![Crystal structures of the sulfones of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2,3-diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one (1)](https://i0.wp.com/journals.iucr.org/logos/jicons/e_36x36.png "Crystal structures of the sulfones of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2,3-diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one (1)")
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![Crystal structures of the sulfones of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2,3-diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one (3)](https://i0.wp.com/journals.iucr.org/logos/buttonlogos/cross.png "Crystal structures of the sulfones of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2,3-diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one (3)")
Acta Cryst. (2023). E79, 221-225
https://doi.org/10.1107/S2056989023001524
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(PDF) Investment, Pass-Through, and Exchange Rates: A Cross ......0 Investment, Pass-Through, and Exchange Rates: A Cross-Country Comparison January 1998 revision Jose Manuel Campa Linda - PDFSLIDE.NETOpen ![Crystal structures of the sulfones of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2,3-diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one (24)](https://i0.wp.com/journals.iucr.org/logos/buttonlogos/open.png "Crystal structures of the sulfones of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2,3-diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one (24)")
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![Crystal structures of the sulfones of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2,3-diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one (26)](https://i0.wp.com/crossmark-cdn.crossref.org/widget/v2.0/logos/CROSSMARK_Color_square_no_text.svg "Crystal structures of the sulfones of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2,3-diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one (26)")
H. P. Yennawar, T. K. Mal, C. N. Pacheco, A. F. Lagalante, M. A. Olsen, M. W. Russell, G. C. Muench, Q. J. Moyer and L. J. Silverberg
The title sulfones crystallize in space group P21/n with two molecules in each of the asymmetric units and have almost identical unit cells and extended structures. In both structures, the thiazine rings exhibit a screw-boat pucker.
Keywords: sulfone; 1,3-thiazin-4-one; screw-boat pucker; S-oxidation; crystal structure.
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Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023001524/hb8054sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2056989023001524/hb80541sup2.hkl | |
MDL mol file https://doi.org/10.1107/S2056989023001524/hb80541sup4.mol | |
Structure factor file (CIF format) https://doi.org/10.1107/S2056989023001524/hb80542sup3.hkl | |
MDL mol file https://doi.org/10.1107/S2056989023001524/hb80542sup5.mol | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989023001524/hb80541sup6.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989023001524/hb80542sup7.cml |
CCDC references: 2236814; 2236815
Computing details top
Data collection: CrysAlis PRO 1.171.42.63a (Rigaku OD, 2022) for (1); SMART V5.634 (Bruker, 2001) for (2). Cell refinement: CrysAlis PRO 1.171.42.63a (Rigaku OD, 2022) for (1); SAINT V6.36A (Bruker, 2001) for (2). Data reduction: CrysAlis PRO 1.171.42.63a (Rigaku OD, 2022) for (1); SAINT V6.36A (Bruker, 2016) for (2). Program(s) used to solve structure: olex2.solve 1.3-ac4 (Bourhis et al., 2015) for (1); SHELXS (Sheldrick, 2008) for (2). For both structures, program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: Olex2 1.3-ac4 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.3-ac4 (Dolomanov et al., 2009).
Crystal data
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| C20H15NO3S | F(000) = 1456 |
| Mr = 349.39 | Dx = 1.394 Mg m−3 |
| Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
| a = 6.8530 (6) Å | Cell parameters from 6963 reflections |
| b = 25.7472 (15) Å | θ = 2.9–70.6° |
| c = 19.0240 (12) Å | µ = 1.89 mm−1 |
| β = 97.394 (7)° | T = 173 K |
| V = 3328.8 (4) Å3 | Block, clear colourless |
| Z = 8 | 0.2 × 0.06 × 0.04 mm |
Data collection
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| ROD, Synergy Custom system, HyPix-Arc 150 diffractometer | 6557 independent reflections |
| Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source | 4087 reflections with I > 2σ(I) |
| Mirror monochromator | Rint = 0.074 |
| Detector resolution: 10.0000 pixels mm-1 | θmax = 75.7°, θmin = 2.9° |
| ω scans | h = −8→8 |
| Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022) | k = −31→31 |
| Tmin = 0.649, Tmax = 1.000 | l = −23→18 |
| 21581 measured reflections |
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| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.092 | w = 1/[σ2(Fo2) + (0.1722P)2 + 1.2363P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.300 | (Δ/σ)max < 0.001 |
| S = 1.10 | Δρmax = 0.66 e Å−3 |
| 6557 reflections | Δρmin = −1.06 e Å−3 |
| 452 parameters | Extinction correction: SHELXL2018/3 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 0 restraints | Extinction coefficient: 0.0038 (5) |
| Primary atom site location: iterative |
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Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
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| x | y | z | Uiso*/Ueq | ||
| S1 | 0.62556 (19) | 0.74906 (4) | 0.62956 (6) | 0.0454 (4) | |
| O1 | 0.4248 (5) | 0.76270 (12) | 0.63479 (18) | 0.0532 (9) | |
| O2 | 0.7399 (6) | 0.78342 (13) | 0.59272 (17) | 0.0608 (10) | |
| O3 | 0.5497 (5) | 0.61116 (11) | 0.74902 (16) | 0.0456 (8) | |
| N1 | 0.6484 (5) | 0.69574 (13) | 0.74977 (18) | 0.0390 (8) | |
| C1 | 0.6386 (7) | 0.68627 (17) | 0.5944 (2) | 0.0407 (10) | |
| C2 | 0.6537 (7) | 0.6796 (2) | 0.5231 (3) | 0.0501 (12) | |
| H2 | 0.654648 | 0.708677 | 0.492500 | 0.060* | |
| C3 | 0.6673 (8) | 0.6295 (2) | 0.4972 (3) | 0.0544 (13) | |
| H3 | 0.680789 | 0.624314 | 0.448640 | 0.065* | |
| C4 | 0.6615 (7) | 0.58719 (19) | 0.5413 (3) | 0.0517 (12) | |
| H4 | 0.668259 | 0.553102 | 0.522656 | 0.062* | |
| C5 | 0.6457 (7) | 0.59407 (18) | 0.6128 (3) | 0.0489 (12) | |
| H5 | 0.643583 | 0.564708 | 0.642941 | 0.059* | |
| C6 | 0.6330 (7) | 0.64378 (17) | 0.6404 (2) | 0.0419 (10) | |
| C7 | 0.6090 (7) | 0.64872 (16) | 0.7171 (2) | 0.0424 (10) | |
| C8 | 0.7557 (7) | 0.73578 (16) | 0.7164 (2) | 0.0428 (10) | |
| H8 | 0.887282 | 0.721153 | 0.709704 | 0.051* | |
| C9 | 0.7905 (7) | 0.78609 (15) | 0.7569 (2) | 0.0399 (10) | |
| C10 | 0.6351 (7) | 0.81491 (17) | 0.7762 (2) | 0.0464 (11) | |
| H10 | 0.504192 | 0.802207 | 0.766774 | 0.056* | |
| C11 | 0.6728 (9) | 0.86284 (18) | 0.8097 (2) | 0.0537 (13) | |
| H11 | 0.566833 | 0.883072 | 0.822377 | 0.064* | |
| C12 | 0.8631 (8) | 0.88091 (18) | 0.8244 (3) | 0.0515 (12) | |
| H12 | 0.888316 | 0.913247 | 0.847853 | 0.062* | |
| C13 | 1.0162 (8) | 0.85202 (19) | 0.8050 (3) | 0.0533 (13) | |
| H13 | 1.147062 | 0.864694 | 0.814852 | 0.064* | |
| C14 | 0.9815 (8) | 0.80463 (18) | 0.7713 (2) | 0.0490 (12) | |
| H14 | 1.088108 | 0.784884 | 0.758093 | 0.059* | |
| C15 | 0.6318 (7) | 0.69896 (16) | 0.8253 (2) | 0.0429 (11) | |
| C16 | 0.7980 (8) | 0.69680 (18) | 0.8737 (2) | 0.0516 (12) | |
| H16 | 0.923333 | 0.691947 | 0.858343 | 0.062* | |
| C17 | 0.7812 (10) | 0.7018 (2) | 0.9453 (3) | 0.0638 (16) | |
| H17 | 0.895753 | 0.700715 | 0.979190 | 0.077* | |
| C18 | 0.6001 (11) | 0.7083 (2) | 0.9673 (3) | 0.0691 (18) | |
| H18 | 0.589298 | 0.712069 | 1.016297 | 0.083* | |
| C19 | 0.4346 (10) | 0.7092 (2) | 0.9185 (3) | 0.0669 (16) | |
| H19 | 0.309207 | 0.713126 | 0.934068 | 0.080* | |
| C20 | 0.4482 (8) | 0.70451 (19) | 0.8461 (3) | 0.0537 (12) | |
| H20 | 0.333554 | 0.705118 | 0.812218 | 0.064* | |
| S2 | 0.13252 (18) | 0.49892 (4) | 0.65164 (6) | 0.0439 (4) | |
| O4 | −0.0701 (5) | 0.48580 (12) | 0.65590 (18) | 0.0540 (9) | |
| O5 | 0.2516 (6) | 0.46129 (12) | 0.62200 (17) | 0.0565 (10) | |
| O6 | 0.0546 (5) | 0.64719 (11) | 0.74688 (16) | 0.0467 (8) | |
| N2 | 0.1453 (6) | 0.56260 (13) | 0.76148 (18) | 0.0408 (9) | |
| C21 | 0.1453 (7) | 0.55831 (17) | 0.6066 (2) | 0.0413 (10) | |
| C22 | 0.1579 (7) | 0.55769 (18) | 0.5345 (2) | 0.0481 (11) | |
| H22 | 0.161209 | 0.525749 | 0.509711 | 0.058* | |
| C23 | 0.1655 (8) | 0.6047 (2) | 0.4994 (2) | 0.0506 (12) | |
| H23 | 0.174775 | 0.605013 | 0.449995 | 0.061* | |
| C24 | 0.1596 (7) | 0.65089 (18) | 0.5357 (3) | 0.0506 (12) | |
| H24 | 0.164357 | 0.682885 | 0.511127 | 0.061* | |
| C25 | 0.1468 (7) | 0.65103 (18) | 0.6081 (2) | 0.0461 (11) | |
| H25 | 0.145517 | 0.683064 | 0.632868 | 0.055* | |
| C26 | 0.1357 (7) | 0.60427 (17) | 0.6446 (2) | 0.0403 (10) | |
| C27 | 0.1111 (7) | 0.60690 (16) | 0.7219 (2) | 0.0420 (10) | |
| C28 | 0.2553 (7) | 0.51938 (16) | 0.7368 (2) | 0.0419 (10) | |
| H28 | 0.387925 | 0.532827 | 0.729278 | 0.050* | |
| C29 | 0.2872 (8) | 0.47302 (16) | 0.7859 (2) | 0.0454 (11) | |
| C30 | 0.1322 (9) | 0.44441 (18) | 0.8061 (2) | 0.0556 (14) | |
| H30 | 0.000299 | 0.454607 | 0.790836 | 0.067* | |
| C31 | 0.1698 (11) | 0.4010 (2) | 0.8486 (3) | 0.0698 (17) | |
| H31 | 0.063439 | 0.381662 | 0.862724 | 0.084* | |
| C32 | 0.3619 (12) | 0.3856 (2) | 0.8706 (3) | 0.078 (2) | |
| H32 | 0.386987 | 0.355338 | 0.898849 | 0.093* | |
| C33 | 0.5153 (11) | 0.4141 (2) | 0.8514 (3) | 0.0766 (19) | |
| H33 | 0.646738 | 0.404008 | 0.867541 | 0.092* | |
| C34 | 0.4806 (9) | 0.4575 (2) | 0.8087 (3) | 0.0590 (14) | |
| H34 | 0.587839 | 0.476665 | 0.794842 | 0.071* | |
| C35 | 0.1235 (7) | 0.56603 (16) | 0.8364 (2) | 0.0434 (11) | |
| C36 | −0.0597 (8) | 0.5610 (2) | 0.8570 (3) | 0.0567 (13) | |
| H36 | −0.172083 | 0.556851 | 0.822632 | 0.068* | |
| C37 | −0.0791 (10) | 0.5620 (2) | 0.9288 (3) | 0.0699 (16) | |
| H37 | −0.205174 | 0.558456 | 0.944078 | 0.084* | |
| C38 | 0.0863 (11) | 0.5680 (3) | 0.9778 (3) | 0.0791 (19) | |
| H38 | 0.073055 | 0.568055 | 1.026936 | 0.095* | |
| C39 | 0.2698 (11) | 0.5741 (3) | 0.9570 (3) | 0.0789 (19) | |
| H39 | 0.381975 | 0.578891 | 0.991238 | 0.095* | |
| C40 | 0.2890 (9) | 0.5731 (2) | 0.8853 (2) | 0.0570 (13) | |
| H40 | 0.414579 | 0.577332 | 0.869928 | 0.068* |
Atomic displacement parameters (Å2)
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| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0655 (9) | 0.0296 (6) | 0.0391 (6) | −0.0001 (5) | −0.0002 (5) | 0.0001 (4) |
| O1 | 0.061 (2) | 0.0395 (17) | 0.057 (2) | 0.0105 (16) | −0.0017 (16) | −0.0030 (15) |
| O2 | 0.097 (3) | 0.0413 (19) | 0.0443 (18) | −0.0202 (18) | 0.0095 (18) | 0.0079 (15) |
| O3 | 0.058 (2) | 0.0301 (15) | 0.0467 (17) | −0.0032 (14) | 0.0004 (14) | −0.0002 (13) |
| N1 | 0.053 (2) | 0.0259 (17) | 0.0377 (19) | −0.0017 (15) | 0.0038 (16) | −0.0035 (14) |
| C1 | 0.050 (3) | 0.033 (2) | 0.039 (2) | 0.0015 (19) | 0.0021 (18) | −0.0064 (18) |
| C2 | 0.057 (3) | 0.048 (3) | 0.042 (3) | −0.005 (2) | −0.003 (2) | 0.000 (2) |
| C3 | 0.059 (3) | 0.057 (3) | 0.046 (3) | 0.000 (3) | 0.001 (2) | −0.013 (2) |
| C4 | 0.060 (3) | 0.044 (3) | 0.050 (3) | 0.000 (2) | 0.002 (2) | −0.021 (2) |
| C5 | 0.056 (3) | 0.035 (2) | 0.053 (3) | 0.003 (2) | −0.004 (2) | −0.008 (2) |
| C6 | 0.055 (3) | 0.032 (2) | 0.038 (2) | 0.0004 (19) | 0.0021 (19) | −0.0066 (18) |
| C7 | 0.054 (3) | 0.024 (2) | 0.048 (3) | 0.0027 (19) | 0.002 (2) | −0.0033 (18) |
| C8 | 0.060 (3) | 0.025 (2) | 0.043 (2) | −0.0033 (19) | 0.007 (2) | −0.0053 (18) |
| C9 | 0.056 (3) | 0.0244 (19) | 0.039 (2) | 0.0002 (18) | 0.0016 (19) | −0.0020 (17) |
| C10 | 0.059 (3) | 0.032 (2) | 0.046 (3) | 0.001 (2) | −0.003 (2) | −0.003 (2) |
| C11 | 0.080 (4) | 0.035 (2) | 0.044 (3) | 0.005 (2) | 0.000 (2) | −0.001 (2) |
| C12 | 0.075 (4) | 0.030 (2) | 0.048 (3) | −0.010 (2) | 0.001 (2) | −0.005 (2) |
| C13 | 0.061 (3) | 0.042 (3) | 0.055 (3) | −0.013 (2) | 0.001 (2) | −0.004 (2) |
| C14 | 0.061 (3) | 0.038 (2) | 0.047 (3) | −0.007 (2) | 0.002 (2) | −0.001 (2) |
| C15 | 0.062 (3) | 0.027 (2) | 0.039 (2) | −0.003 (2) | 0.006 (2) | −0.0033 (18) |
| C16 | 0.069 (3) | 0.043 (3) | 0.039 (2) | −0.005 (2) | −0.007 (2) | 0.005 (2) |
| C17 | 0.102 (5) | 0.047 (3) | 0.038 (3) | −0.004 (3) | −0.006 (3) | 0.001 (2) |
| C18 | 0.128 (6) | 0.038 (3) | 0.043 (3) | −0.012 (3) | 0.020 (3) | −0.003 (2) |
| C19 | 0.097 (5) | 0.047 (3) | 0.063 (3) | −0.009 (3) | 0.033 (3) | −0.014 (3) |
| C20 | 0.067 (3) | 0.042 (3) | 0.055 (3) | 0.000 (2) | 0.017 (2) | −0.009 (2) |
| S2 | 0.0639 (8) | 0.0257 (5) | 0.0396 (6) | 0.0007 (5) | −0.0026 (5) | −0.0015 (4) |
| O4 | 0.063 (2) | 0.0390 (17) | 0.057 (2) | −0.0106 (16) | −0.0041 (16) | 0.0020 (15) |
| O5 | 0.087 (3) | 0.0370 (17) | 0.0442 (18) | 0.0210 (17) | 0.0040 (17) | −0.0065 (14) |
| O6 | 0.060 (2) | 0.0281 (15) | 0.0503 (18) | 0.0065 (14) | 0.0026 (15) | −0.0040 (14) |
| N2 | 0.056 (2) | 0.0279 (17) | 0.0372 (19) | −0.0005 (16) | 0.0035 (16) | 0.0005 (15) |
| C21 | 0.051 (3) | 0.031 (2) | 0.039 (2) | 0.0002 (19) | −0.0025 (19) | 0.0034 (18) |
| C22 | 0.059 (3) | 0.041 (2) | 0.043 (2) | 0.006 (2) | 0.001 (2) | −0.006 (2) |
| C23 | 0.061 (3) | 0.052 (3) | 0.038 (2) | 0.005 (2) | 0.004 (2) | 0.008 (2) |
| C24 | 0.058 (3) | 0.037 (2) | 0.056 (3) | 0.001 (2) | 0.004 (2) | 0.016 (2) |
| C25 | 0.053 (3) | 0.034 (2) | 0.050 (3) | 0.000 (2) | 0.000 (2) | 0.004 (2) |
| C26 | 0.050 (3) | 0.032 (2) | 0.038 (2) | 0.0057 (18) | −0.0014 (18) | 0.0016 (18) |
| C27 | 0.052 (3) | 0.029 (2) | 0.043 (2) | −0.0015 (19) | −0.0007 (19) | 0.0006 (19) |
| C28 | 0.060 (3) | 0.030 (2) | 0.035 (2) | 0.001 (2) | 0.0034 (19) | −0.0011 (18) |
| C29 | 0.071 (3) | 0.028 (2) | 0.035 (2) | 0.003 (2) | −0.002 (2) | −0.0009 (18) |
| C30 | 0.091 (4) | 0.035 (2) | 0.041 (3) | −0.004 (2) | 0.007 (2) | 0.002 (2) |
| C31 | 0.125 (6) | 0.038 (3) | 0.046 (3) | −0.002 (3) | 0.012 (3) | 0.003 (2) |
| C32 | 0.142 (7) | 0.042 (3) | 0.045 (3) | 0.018 (4) | −0.004 (4) | 0.009 (2) |
| C33 | 0.109 (5) | 0.057 (3) | 0.057 (3) | 0.023 (4) | −0.018 (3) | 0.004 (3) |
| C34 | 0.079 (4) | 0.043 (3) | 0.049 (3) | 0.011 (3) | −0.013 (3) | 0.000 (2) |
| C35 | 0.062 (3) | 0.030 (2) | 0.039 (2) | 0.003 (2) | 0.008 (2) | 0.0006 (18) |
| C36 | 0.064 (3) | 0.053 (3) | 0.054 (3) | 0.003 (3) | 0.011 (2) | 0.009 (2) |
| C37 | 0.087 (5) | 0.069 (4) | 0.057 (3) | 0.013 (3) | 0.022 (3) | 0.008 (3) |
| C38 | 0.114 (6) | 0.076 (4) | 0.050 (3) | 0.006 (4) | 0.021 (4) | −0.005 (3) |
| C39 | 0.106 (5) | 0.088 (5) | 0.040 (3) | −0.006 (4) | −0.003 (3) | −0.007 (3) |
| C40 | 0.074 (4) | 0.055 (3) | 0.039 (3) | −0.005 (3) | −0.004 (2) | −0.005 (2) |
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| S1—O1 | 1.436 (4) | S2—O4 | 1.442 (4) |
| S1—O2 | 1.425 (3) | S2—O5 | 1.429 (3) |
| S1—C1 | 1.756 (4) | S2—C21 | 1.760 (4) |
| S1—C8 | 1.806 (5) | S2—C28 | 1.805 (4) |
| O3—C7 | 1.239 (5) | O6—C27 | 1.224 (5) |
| N1—C7 | 1.372 (5) | N2—C27 | 1.370 (5) |
| N1—C8 | 1.459 (5) | N2—C28 | 1.455 (5) |
| N1—C15 | 1.458 (5) | N2—C35 | 1.454 (5) |
| C1—C2 | 1.383 (6) | C21—C22 | 1.385 (6) |
| C1—C6 | 1.405 (6) | C21—C26 | 1.393 (6) |
| C2—H2 | 0.9500 | C22—H22 | 0.9500 |
| C2—C3 | 1.387 (7) | C22—C23 | 1.386 (6) |
| C3—H3 | 0.9500 | C23—H23 | 0.9500 |
| C3—C4 | 1.378 (7) | C23—C24 | 1.380 (7) |
| C4—H4 | 0.9500 | C24—H24 | 0.9500 |
| C4—C5 | 1.390 (6) | C24—C25 | 1.392 (6) |
| C5—H5 | 0.9500 | C25—H25 | 0.9500 |
| C5—C6 | 1.390 (6) | C25—C26 | 1.397 (6) |
| C6—C7 | 1.494 (6) | C26—C27 | 1.502 (6) |
| C8—H8 | 1.0000 | C28—H28 | 1.0000 |
| C8—C9 | 1.510 (5) | C28—C29 | 1.514 (6) |
| C9—C10 | 1.386 (6) | C29—C30 | 1.387 (7) |
| C9—C14 | 1.387 (7) | C29—C34 | 1.399 (7) |
| C10—H10 | 0.9500 | C30—H30 | 0.9500 |
| C10—C11 | 1.398 (6) | C30—C31 | 1.383 (7) |
| C11—H11 | 0.9500 | C31—H31 | 0.9500 |
| C11—C12 | 1.379 (7) | C31—C32 | 1.387 (9) |
| C12—H12 | 0.9500 | C32—H32 | 0.9500 |
| C12—C13 | 1.375 (7) | C32—C33 | 1.370 (9) |
| C13—H13 | 0.9500 | C33—H33 | 0.9500 |
| C13—C14 | 1.385 (6) | C33—C34 | 1.383 (7) |
| C14—H14 | 0.9500 | C34—H34 | 0.9500 |
| C15—C16 | 1.370 (6) | C35—C36 | 1.369 (7) |
| C15—C20 | 1.375 (7) | C35—C40 | 1.383 (6) |
| C16—H16 | 0.9500 | C36—H36 | 0.9500 |
| C16—C17 | 1.388 (7) | C36—C37 | 1.391 (7) |
| C17—H17 | 0.9500 | C37—H37 | 0.9500 |
| C17—C18 | 1.370 (9) | C37—C38 | 1.381 (9) |
| C18—H18 | 0.9500 | C38—H38 | 0.9500 |
| C18—C19 | 1.370 (9) | C38—C39 | 1.375 (9) |
| C19—H19 | 0.9500 | C39—H39 | 0.9500 |
| C19—C20 | 1.397 (7) | C39—C40 | 1.387 (7) |
| C20—H20 | 0.9500 | C40—H40 | 0.9500 |
| O1—S1—C1 | 110.4 (2) | O4—S2—C21 | 109.8 (2) |
| O1—S1—C8 | 110.4 (2) | O4—S2—C28 | 111.0 (2) |
| O2—S1—O1 | 118.4 (2) | O5—S2—O4 | 117.8 (2) |
| O2—S1—C1 | 109.0 (2) | O5—S2—C21 | 109.3 (2) |
| O2—S1—C8 | 109.2 (2) | O5—S2—C28 | 109.2 (2) |
| C1—S1—C8 | 97.5 (2) | C21—S2—C28 | 97.9 (2) |
| C7—N1—C8 | 120.4 (4) | C27—N2—C28 | 121.2 (4) |
| C7—N1—C15 | 117.5 (4) | C27—N2—C35 | 117.1 (4) |
| C15—N1—C8 | 119.8 (3) | C35—N2—C28 | 119.0 (3) |
| C2—C1—S1 | 120.2 (4) | C22—C21—S2 | 119.0 (3) |
| C2—C1—C6 | 121.6 (4) | C22—C21—C26 | 122.5 (4) |
| C6—C1—S1 | 118.2 (3) | C26—C21—S2 | 118.5 (3) |
| C1—C2—H2 | 120.6 | C21—C22—H22 | 120.7 |
| C1—C2—C3 | 118.7 (5) | C21—C22—C23 | 118.6 (4) |
| C3—C2—H2 | 120.6 | C23—C22—H22 | 120.7 |
| C2—C3—H3 | 119.7 | C22—C23—H23 | 119.8 |
| C4—C3—C2 | 120.6 (4) | C24—C23—C22 | 120.4 (4) |
| C4—C3—H3 | 119.7 | C24—C23—H23 | 119.8 |
| C3—C4—H4 | 119.8 | C23—C24—H24 | 119.7 |
| C3—C4—C5 | 120.5 (4) | C23—C24—C25 | 120.5 (4) |
| C5—C4—H4 | 119.8 | C25—C24—H24 | 119.7 |
| C4—C5—H5 | 119.9 | C24—C25—H25 | 119.9 |
| C4—C5—C6 | 120.2 (5) | C24—C25—C26 | 120.3 (4) |
| C6—C5—H5 | 119.9 | C26—C25—H25 | 119.9 |
| C1—C6—C7 | 123.9 (4) | C21—C26—C25 | 117.7 (4) |
| C5—C6—C1 | 118.3 (4) | C21—C26—C27 | 124.4 (4) |
| C5—C6—C7 | 117.8 (4) | C25—C26—C27 | 117.9 (4) |
| O3—C7—N1 | 121.6 (4) | O6—C27—N2 | 122.1 (4) |
| O3—C7—C6 | 119.8 (4) | O6—C27—C26 | 119.9 (4) |
| N1—C7—C6 | 118.6 (4) | N2—C27—C26 | 117.9 (4) |
| S1—C8—H8 | 107.6 | S2—C28—H28 | 107.4 |
| N1—C8—S1 | 108.3 (3) | N2—C28—S2 | 108.2 (3) |
| N1—C8—H8 | 107.6 | N2—C28—H28 | 107.4 |
| N1—C8—C9 | 116.0 (4) | N2—C28—C29 | 116.3 (4) |
| C9—C8—S1 | 109.3 (3) | C29—C28—S2 | 109.7 (3) |
| C9—C8—H8 | 107.6 | C29—C28—H28 | 107.4 |
| C10—C9—C8 | 121.2 (4) | C30—C29—C28 | 122.3 (5) |
| C10—C9—C14 | 120.1 (4) | C30—C29—C34 | 119.4 (5) |
| C14—C9—C8 | 118.6 (4) | C34—C29—C28 | 118.2 (5) |
| C9—C10—H10 | 120.3 | C29—C30—H30 | 120.0 |
| C9—C10—C11 | 119.4 (5) | C31—C30—C29 | 119.9 (6) |
| C11—C10—H10 | 120.3 | C31—C30—H30 | 120.0 |
| C10—C11—H11 | 119.8 | C30—C31—H31 | 119.8 |
| C12—C11—C10 | 120.3 (5) | C30—C31—C32 | 120.4 (6) |
| C12—C11—H11 | 119.8 | C32—C31—H31 | 119.8 |
| C11—C12—H12 | 120.1 | C31—C32—H32 | 120.1 |
| C13—C12—C11 | 119.8 (5) | C33—C32—C31 | 119.8 (5) |
| C13—C12—H12 | 120.1 | C33—C32—H32 | 120.1 |
| C12—C13—H13 | 119.7 | C32—C33—H33 | 119.7 |
| C12—C13—C14 | 120.6 (5) | C32—C33—C34 | 120.6 (6) |
| C14—C13—H13 | 119.7 | C34—C33—H33 | 119.7 |
| C9—C14—H14 | 120.1 | C29—C34—H34 | 120.1 |
| C13—C14—C9 | 119.7 (5) | C33—C34—C29 | 119.8 (6) |
| C13—C14—H14 | 120.1 | C33—C34—H34 | 120.1 |
| C16—C15—N1 | 119.7 (4) | C36—C35—N2 | 119.2 (4) |
| C16—C15—C20 | 121.6 (5) | C36—C35—C40 | 121.5 (5) |
| C20—C15—N1 | 118.7 (4) | C40—C35—N2 | 119.3 (4) |
| C15—C16—H16 | 120.4 | C35—C36—H36 | 120.4 |
| C15—C16—C17 | 119.3 (5) | C35—C36—C37 | 119.2 (5) |
| C17—C16—H16 | 120.4 | C37—C36—H36 | 120.4 |
| C16—C17—H17 | 119.9 | C36—C37—H37 | 120.3 |
| C18—C17—C16 | 120.3 (5) | C38—C37—C36 | 119.4 (6) |
| C18—C17—H17 | 119.9 | C38—C37—H37 | 120.3 |
| C17—C18—H18 | 120.0 | C37—C38—H38 | 119.3 |
| C17—C18—C19 | 119.9 (5) | C39—C38—C37 | 121.3 (6) |
| C19—C18—H18 | 120.0 | C39—C38—H38 | 119.3 |
| C18—C19—H19 | 119.6 | C38—C39—H39 | 120.4 |
| C18—C19—C20 | 120.8 (6) | C38—C39—C40 | 119.2 (6) |
| C20—C19—H19 | 119.6 | C40—C39—H39 | 120.4 |
| C15—C20—C19 | 118.2 (5) | C35—C40—C39 | 119.4 (6) |
| C15—C20—H20 | 120.9 | C35—C40—H40 | 120.3 |
| C19—C20—H20 | 120.9 | C39—C40—H40 | 120.3 |
| S1—C1—C2—C3 | 178.8 (4) | S2—C21—C22—C23 | 179.2 (4) |
| S1—C1—C6—C5 | −179.3 (4) | S2—C21—C26—C25 | 179.8 (3) |
| S1—C1—C6—C7 | 2.4 (6) | S2—C21—C26—C27 | −1.2 (7) |
| S1—C8—C9—C10 | 65.3 (5) | S2—C28—C29—C30 | −62.1 (5) |
| S1—C8—C9—C14 | −111.2 (4) | S2—C28—C29—C34 | 114.8 (4) |
| O1—S1—C1—C2 | 98.3 (4) | O4—S2—C21—C22 | −95.0 (4) |
| O1—S1—C1—C6 | −81.6 (4) | O4—S2—C21—C26 | 82.9 (4) |
| O1—S1—C8—N1 | 55.2 (3) | O4—S2—C28—N2 | −56.2 (3) |
| O1—S1—C8—C9 | −72.2 (4) | O4—S2—C28—C29 | 71.6 (4) |
| O2—S1—C1—C2 | −33.3 (5) | O5—S2—C21—C22 | 35.7 (4) |
| O2—S1—C1—C6 | 146.8 (4) | O5—S2—C21—C26 | −146.4 (4) |
| O2—S1—C8—N1 | −173.1 (3) | O5—S2—C28—N2 | 172.3 (3) |
| O2—S1—C8—C9 | 59.6 (4) | O5—S2—C28—C29 | −59.9 (4) |
| N1—C8—C9—C10 | −57.5 (6) | N2—C28—C29—C30 | 61.0 (6) |
| N1—C8—C9—C14 | 125.9 (5) | N2—C28—C29—C34 | −122.0 (5) |
| N1—C15—C16—C17 | 177.7 (4) | N2—C35—C36—C37 | 177.2 (5) |
| N1—C15—C20—C19 | −178.0 (4) | N2—C35—C40—C39 | −177.1 (5) |
| C1—S1—C8—N1 | −59.9 (3) | C21—S2—C28—N2 | 58.7 (3) |
| C1—S1—C8—C9 | 172.8 (3) | C21—S2—C28—C29 | −173.5 (4) |
| C1—C2—C3—C4 | 1.5 (8) | C21—C22—C23—C24 | −0.3 (8) |
| C1—C6—C7—O3 | 159.3 (4) | C21—C26—C27—O6 | −161.4 (4) |
| C1—C6—C7—N1 | −18.8 (7) | C21—C26—C27—N2 | 15.7 (7) |
| C2—C1—C6—C5 | 0.8 (7) | C22—C21—C26—C25 | −2.4 (7) |
| C2—C1—C6—C7 | −177.5 (4) | C22—C21—C26—C27 | 176.6 (4) |
| C2—C3—C4—C5 | −1.3 (8) | C22—C23—C24—C25 | 0.3 (8) |
| C3—C4—C5—C6 | 0.9 (8) | C23—C24—C25—C26 | −1.3 (7) |
| C4—C5—C6—C1 | −0.6 (7) | C24—C25—C26—C21 | 2.3 (7) |
| C4—C5—C6—C7 | 177.8 (4) | C24—C25—C26—C27 | −176.8 (4) |
| C5—C6—C7—O3 | −19.0 (7) | C25—C26—C27—O6 | 17.6 (7) |
| C5—C6—C7—N1 | 162.8 (4) | C25—C26—C27—N2 | −165.3 (4) |
| C6—C1—C2—C3 | −1.3 (7) | C26—C21—C22—C23 | 1.4 (8) |
| C7—N1—C8—S1 | 56.4 (5) | C27—N2—C28—S2 | −57.3 (5) |
| C7—N1—C8—C9 | 179.8 (4) | C27—N2—C28—C29 | 178.8 (4) |
| C7—N1—C15—C16 | 100.3 (5) | C27—N2—C35—C36 | 83.8 (5) |
| C7—N1—C15—C20 | −80.1 (5) | C27—N2—C35—C40 | −97.7 (5) |
| C8—S1—C1—C2 | −146.7 (4) | C28—S2—C21—C22 | 149.2 (4) |
| C8—S1—C1—C6 | 33.4 (4) | C28—S2—C21—C26 | −32.9 (4) |
| C8—N1—C7—O3 | 167.2 (4) | C28—N2—C27—O6 | −165.2 (4) |
| C8—N1—C7—C6 | −14.7 (6) | C28—N2—C27—C26 | 17.7 (6) |
| C8—N1—C15—C16 | −62.6 (5) | C28—N2—C35—C36 | −114.4 (5) |
| C8—N1—C15—C20 | 117.0 (5) | C28—N2—C35—C40 | 64.1 (6) |
| C8—C9—C10—C11 | −176.0 (4) | C28—C29—C30—C31 | 177.1 (4) |
| C8—C9—C14—C13 | 176.6 (4) | C28—C29—C34—C33 | −177.5 (5) |
| C9—C10—C11—C12 | −1.0 (7) | C29—C30—C31—C32 | −0.6 (8) |
| C10—C9—C14—C13 | 0.0 (7) | C30—C29—C34—C33 | −0.5 (7) |
| C10—C11—C12—C13 | 1.0 (7) | C30—C31—C32—C33 | 1.4 (9) |
| C11—C12—C13—C14 | −0.5 (7) | C31—C32—C33—C34 | −1.7 (9) |
| C12—C13—C14—C9 | 0.0 (7) | C32—C33—C34—C29 | 1.2 (8) |
| C14—C9—C10—C11 | 0.5 (7) | C34—C29—C30—C31 | 0.2 (7) |
| C15—N1—C7—O3 | 4.4 (7) | C35—N2—C27—O6 | −3.8 (7) |
| C15—N1—C7—C6 | −177.5 (4) | C35—N2—C27—C26 | 179.1 (4) |
| C15—N1—C8—S1 | −141.2 (3) | C35—N2—C28—S2 | 141.6 (3) |
| C15—N1—C8—C9 | −17.8 (6) | C35—N2—C28—C29 | 17.7 (6) |
| C15—C16—C17—C18 | 0.7 (8) | C35—C36—C37—C38 | 0.1 (8) |
| C16—C15—C20—C19 | 1.5 (7) | C36—C35—C40—C39 | 1.4 (8) |
| C16—C17—C18—C19 | 0.7 (8) | C36—C37—C38—C39 | 1.2 (10) |
| C17—C18—C19—C20 | −1.0 (8) | C37—C38—C39—C40 | −1.1 (10) |
| C18—C19—C20—C15 | −0.1 (7) | C38—C39—C40—C35 | −0.1 (9) |
| C20—C15—C16—C17 | −1.8 (7) | C40—C35—C36—C37 | −1.3 (8) |
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| D—H···A | D—H | H···A | D···A | D—H···A |
| C3—H3···O5i | 0.95 | 2.65 | 3.353 (6) | 131 |
| C8—H8···O6ii | 1.00 | 2.29 | 3.070 (6) | 134 |
| C16—H16···O6ii | 0.95 | 2.67 | 3.410 (6) | 135 |
| C20—H20···O6 | 0.95 | 2.61 | 3.422 (6) | 144 |
| C28—H28···O3 | 1.00 | 2.31 | 3.096 (5) | 135 |
| C36—H36···O3iii | 0.95 | 2.62 | 3.412 (6) | 141 |
| C40—H40···O3 | 0.95 | 2.73 | 3.473 (7) | 136 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, y, z.
Crystal data
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| C19H14N2O3S | F(000) = 1456 |
| Mr = 350.38 | Dx = 1.406 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| a = 6.8584 (19) Å | Cell parameters from 5480 reflections |
| b = 25.487 (7) Å | θ = 2.3–26.1° |
| c = 19.008 (5) Å | µ = 0.22 mm−1 |
| β = 94.669 (7)° | T = 298 K |
| V = 3311.6 (16) Å3 | Needle, colorless |
| Z = 8 | 0.22 × 0.04 × 0.02 mm |
Data collection
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| Bruker CCD area detector diffractometer | 5509 reflections with I > 2σ(I) |
| phi and ω scans | Rint = 0.040 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | θmax = 28.4°, θmin = 1.3° |
| Tmin = 0.237, Tmax = 0.9 | h = −9→9 |
| 29524 measured reflections | k = −32→32 |
| 7909 independent reflections | l = −23→24 |
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| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
| wR(F2) = 0.138 | w = 1/[σ2(Fo2) + (0.0689P)2 + 0.239P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max = 0.001 |
| 7909 reflections | Δρmax = 0.31 e Å−3 |
| 451 parameters | Δρmin = −0.26 e Å−3 |
| 0 restraints |
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Experimental. The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of ω scans each set at different φ and/or 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 5.82 cm. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
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| x | y | z | Uiso*/Ueq | ||
| S1 | 0.63430 (8) | 0.74816 (2) | 0.62562 (3) | 0.04230 (15) | |
| O1 | 0.4325 (2) | 0.75929 (6) | 0.63311 (8) | 0.0578 (4) | |
| O2 | 0.7474 (3) | 0.78399 (6) | 0.58785 (8) | 0.0681 (5) | |
| O3 | 0.5672 (2) | 0.60846 (5) | 0.74613 (7) | 0.0460 (3) | |
| N1 | 0.6591 (2) | 0.69392 (5) | 0.74620 (8) | 0.0339 (3) | |
| C1 | 0.6539 (3) | 0.68391 (7) | 0.59048 (10) | 0.0372 (4) | |
| N2 | 0.6667 (3) | 0.68078 (7) | 0.52113 (9) | 0.0485 (4) | |
| C3 | 0.6840 (3) | 0.63236 (9) | 0.49538 (11) | 0.0536 (6) | |
| H3 | 0.693463 | 0.628667 | 0.447104 | 0.064* | |
| C4 | 0.6885 (3) | 0.58773 (8) | 0.53596 (11) | 0.0484 (5) | |
| H4 | 0.702610 | 0.554955 | 0.515465 | 0.058* | |
| C5 | 0.6718 (3) | 0.59221 (7) | 0.60787 (11) | 0.0409 (5) | |
| H5 | 0.672293 | 0.562470 | 0.636234 | 0.049* | |
| C6 | 0.6543 (3) | 0.64206 (7) | 0.63705 (10) | 0.0342 (4) | |
| C7 | 0.6251 (3) | 0.64642 (7) | 0.71450 (10) | 0.0348 (4) | |
| C8 | 0.7641 (3) | 0.73481 (6) | 0.71038 (9) | 0.0329 (4) | |
| H8 | 0.892706 | 0.720657 | 0.701537 | 0.039* | |
| C9 | 0.7973 (3) | 0.78510 (6) | 0.75095 (9) | 0.0349 (4) | |
| C10 | 0.6433 (3) | 0.81482 (7) | 0.77271 (11) | 0.0434 (5) | |
| H10 | 0.515080 | 0.803440 | 0.763175 | 0.052* | |
| C11 | 0.6813 (4) | 0.86115 (8) | 0.80844 (11) | 0.0521 (6) | |
| H11 | 0.578441 | 0.880859 | 0.823488 | 0.062* | |
| C12 | 0.8701 (4) | 0.87842 (8) | 0.82198 (12) | 0.0566 (6) | |
| H12 | 0.894905 | 0.909751 | 0.846138 | 0.068* | |
| C13 | 1.0224 (4) | 0.84948 (9) | 0.79988 (12) | 0.0586 (6) | |
| H13 | 1.150197 | 0.861340 | 0.808938 | 0.070* | |
| C14 | 0.9866 (3) | 0.80271 (8) | 0.76418 (11) | 0.0465 (5) | |
| H14 | 1.090055 | 0.783227 | 0.749150 | 0.056* | |
| C15 | 0.6365 (3) | 0.69882 (7) | 0.82159 (10) | 0.0386 (4) | |
| C16 | 0.7981 (4) | 0.69689 (8) | 0.86865 (11) | 0.0536 (6) | |
| H16 | 0.920527 | 0.689583 | 0.853283 | 0.064* | |
| C17 | 0.7772 (5) | 0.70596 (10) | 0.93957 (13) | 0.0721 (7) | |
| H17 | 0.886765 | 0.705311 | 0.971784 | 0.087* | |
| C18 | 0.5986 (5) | 0.71578 (10) | 0.96239 (14) | 0.0763 (9) | |
| H18 | 0.586778 | 0.722023 | 1.010056 | 0.092* | |
| C19 | 0.4354 (5) | 0.71657 (10) | 0.91580 (16) | 0.0763 (8) | |
| H19 | 0.313012 | 0.722843 | 0.931876 | 0.092* | |
| C20 | 0.4533 (3) | 0.70791 (9) | 0.84404 (13) | 0.0576 (6) | |
| H20 | 0.343538 | 0.708267 | 0.811932 | 0.069* | |
| S2 | 0.13994 (8) | 0.49436 (2) | 0.65360 (2) | 0.03987 (15) | |
| O4 | −0.0638 (2) | 0.48498 (5) | 0.66084 (8) | 0.0538 (4) | |
| O5 | 0.2549 (3) | 0.45389 (5) | 0.62563 (8) | 0.0642 (5) | |
| O6 | 0.0749 (2) | 0.64799 (5) | 0.73881 (7) | 0.0468 (4) | |
| N3 | 0.1540 (2) | 0.56289 (5) | 0.75909 (8) | 0.0356 (4) | |
| C21 | 0.1620 (3) | 0.55275 (6) | 0.60387 (10) | 0.0348 (4) | |
| N4 | 0.1748 (2) | 0.54607 (6) | 0.53518 (8) | 0.0432 (4) | |
| C23 | 0.1843 (3) | 0.58965 (8) | 0.49718 (11) | 0.0485 (5) | |
| H23 | 0.191493 | 0.586542 | 0.448712 | 0.058* | |
| C24 | 0.1841 (3) | 0.63940 (8) | 0.52628 (11) | 0.0469 (5) | |
| H24 | 0.192899 | 0.668864 | 0.497855 | 0.056* | |
| C25 | 0.1706 (3) | 0.64482 (7) | 0.59793 (11) | 0.0410 (5) | |
| H25 | 0.169557 | 0.677987 | 0.618283 | 0.049* | |
| C26 | 0.1587 (2) | 0.60021 (6) | 0.63938 (9) | 0.0327 (4) | |
| C27 | 0.1291 (3) | 0.60600 (7) | 0.71683 (10) | 0.0354 (4) | |
| C28 | 0.2623 (3) | 0.51705 (6) | 0.73556 (9) | 0.0340 (4) | |
| H28 | 0.392932 | 0.529097 | 0.725573 | 0.041* | |
| C29 | 0.2885 (3) | 0.47234 (7) | 0.78757 (10) | 0.0416 (5) | |
| C30 | 0.1352 (4) | 0.44247 (8) | 0.80797 (11) | 0.0533 (6) | |
| H30 | 0.007471 | 0.450892 | 0.791761 | 0.064* | |
| C31 | 0.1710 (5) | 0.40003 (9) | 0.85245 (13) | 0.0733 (8) | |
| H31 | 0.067265 | 0.379812 | 0.865727 | 0.088* | |
| C32 | 0.3580 (6) | 0.38766 (11) | 0.87699 (14) | 0.0930 (11) | |
| H32 | 0.381106 | 0.359142 | 0.907028 | 0.112* | |
| C33 | 0.5112 (5) | 0.41710 (12) | 0.85749 (15) | 0.0914 (10) | |
| H33 | 0.638235 | 0.408655 | 0.874614 | 0.110* | |
| C34 | 0.4785 (4) | 0.45936 (9) | 0.81249 (13) | 0.0633 (6) | |
| H34 | 0.583346 | 0.479040 | 0.798928 | 0.076* | |
| C35 | 0.1232 (3) | 0.56794 (7) | 0.83321 (10) | 0.0422 (5) | |
| C36 | −0.0608 (4) | 0.55993 (9) | 0.85463 (13) | 0.0618 (6) | |
| H36 | −0.165756 | 0.553010 | 0.821831 | 0.074* | |
| C37 | −0.0874 (5) | 0.56238 (12) | 0.92666 (17) | 0.0913 (10) | |
| H37 | −0.210699 | 0.556903 | 0.942374 | 0.110* | |
| C38 | 0.0697 (7) | 0.57292 (14) | 0.97419 (16) | 0.1078 (12) | |
| H38 | 0.052867 | 0.573858 | 1.022227 | 0.129* | |
| C39 | 0.2486 (6) | 0.58194 (15) | 0.95149 (15) | 0.1071 (12) | |
| H39 | 0.353065 | 0.589783 | 0.984069 | 0.129* | |
| C40 | 0.2778 (4) | 0.57965 (10) | 0.88050 (12) | 0.0692 (7) | |
| H40 | 0.400987 | 0.585986 | 0.865134 | 0.083* |
Atomic displacement parameters (Å2)
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| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0610 (4) | 0.0304 (2) | 0.0346 (3) | 0.0002 (2) | −0.0017 (2) | −0.00136 (19) |
| O1 | 0.0600 (10) | 0.0494 (8) | 0.0608 (10) | 0.0194 (7) | −0.0144 (8) | −0.0116 (7) |
| O2 | 0.1144 (14) | 0.0454 (9) | 0.0452 (9) | −0.0225 (9) | 0.0100 (9) | 0.0039 (7) |
| O3 | 0.0600 (9) | 0.0318 (7) | 0.0461 (8) | −0.0101 (6) | 0.0053 (7) | −0.0014 (6) |
| N1 | 0.0438 (9) | 0.0268 (7) | 0.0309 (8) | −0.0005 (6) | 0.0024 (7) | −0.0046 (6) |
| C1 | 0.0402 (11) | 0.0361 (9) | 0.0349 (10) | 0.0008 (8) | 0.0009 (8) | −0.0062 (8) |
| N2 | 0.0591 (11) | 0.0516 (10) | 0.0347 (9) | −0.0033 (8) | 0.0032 (8) | −0.0088 (8) |
| C3 | 0.0576 (14) | 0.0645 (14) | 0.0385 (12) | −0.0032 (11) | 0.0019 (10) | −0.0208 (11) |
| C4 | 0.0447 (12) | 0.0473 (11) | 0.0531 (13) | −0.0001 (9) | 0.0036 (10) | −0.0232 (10) |
| C5 | 0.0395 (11) | 0.0353 (10) | 0.0473 (12) | 0.0008 (8) | −0.0003 (9) | −0.0110 (8) |
| C6 | 0.0326 (10) | 0.0308 (9) | 0.0389 (10) | −0.0009 (7) | 0.0012 (8) | −0.0095 (7) |
| C7 | 0.0355 (10) | 0.0298 (9) | 0.0385 (10) | 0.0002 (7) | −0.0008 (8) | −0.0051 (8) |
| C8 | 0.0362 (10) | 0.0277 (8) | 0.0344 (10) | 0.0000 (7) | 0.0011 (8) | −0.0026 (7) |
| C9 | 0.0458 (11) | 0.0249 (8) | 0.0334 (10) | −0.0018 (7) | 0.0002 (8) | −0.0012 (7) |
| C10 | 0.0490 (12) | 0.0327 (9) | 0.0477 (12) | 0.0019 (8) | −0.0012 (9) | −0.0064 (8) |
| C11 | 0.0706 (16) | 0.0340 (10) | 0.0513 (13) | 0.0069 (10) | 0.0034 (11) | −0.0091 (9) |
| C12 | 0.0846 (18) | 0.0377 (11) | 0.0478 (13) | −0.0140 (11) | 0.0078 (12) | −0.0137 (10) |
| C13 | 0.0616 (15) | 0.0550 (13) | 0.0587 (15) | −0.0228 (11) | 0.0017 (12) | −0.0157 (11) |
| C14 | 0.0502 (13) | 0.0427 (11) | 0.0466 (12) | −0.0043 (9) | 0.0038 (10) | −0.0091 (9) |
| C15 | 0.0544 (12) | 0.0278 (9) | 0.0342 (10) | −0.0031 (8) | 0.0074 (9) | −0.0057 (7) |
| C16 | 0.0689 (15) | 0.0515 (12) | 0.0396 (12) | 0.0056 (11) | −0.0005 (11) | −0.0025 (10) |
| C17 | 0.110 (2) | 0.0658 (16) | 0.0388 (13) | 0.0026 (15) | −0.0039 (14) | −0.0051 (12) |
| C18 | 0.135 (3) | 0.0554 (15) | 0.0415 (14) | −0.0112 (16) | 0.0260 (17) | −0.0101 (11) |
| C19 | 0.098 (2) | 0.0676 (17) | 0.0699 (19) | −0.0138 (15) | 0.0470 (17) | −0.0170 (14) |
| C20 | 0.0604 (15) | 0.0546 (13) | 0.0598 (15) | −0.0074 (11) | 0.0178 (12) | −0.0099 (11) |
| S2 | 0.0619 (3) | 0.0239 (2) | 0.0325 (3) | 0.0015 (2) | −0.0038 (2) | −0.00153 (18) |
| O4 | 0.0589 (10) | 0.0428 (8) | 0.0571 (9) | −0.0192 (7) | −0.0116 (7) | 0.0086 (7) |
| O5 | 0.1104 (14) | 0.0397 (8) | 0.0414 (9) | 0.0282 (8) | −0.0011 (8) | −0.0074 (6) |
| O6 | 0.0610 (9) | 0.0305 (7) | 0.0485 (8) | 0.0107 (6) | 0.0025 (7) | −0.0063 (6) |
| N3 | 0.0479 (10) | 0.0271 (7) | 0.0316 (8) | 0.0024 (6) | 0.0031 (7) | −0.0017 (6) |
| C21 | 0.0401 (11) | 0.0308 (9) | 0.0330 (10) | 0.0023 (7) | −0.0005 (8) | 0.0036 (7) |
| N4 | 0.0545 (11) | 0.0441 (9) | 0.0307 (9) | 0.0005 (7) | 0.0023 (7) | 0.0013 (7) |
| C23 | 0.0561 (13) | 0.0559 (13) | 0.0332 (11) | 0.0003 (10) | 0.0026 (9) | 0.0088 (9) |
| C24 | 0.0473 (12) | 0.0451 (11) | 0.0479 (12) | −0.0036 (9) | 0.0014 (10) | 0.0175 (9) |
| C25 | 0.0416 (11) | 0.0301 (9) | 0.0503 (12) | −0.0004 (8) | −0.0018 (9) | 0.0051 (8) |
| C26 | 0.0316 (10) | 0.0288 (8) | 0.0373 (10) | 0.0006 (7) | −0.0002 (8) | 0.0001 (7) |
| C27 | 0.0369 (10) | 0.0291 (9) | 0.0392 (10) | −0.0010 (7) | −0.0019 (8) | −0.0042 (7) |
| C28 | 0.0424 (10) | 0.0265 (8) | 0.0324 (9) | 0.0014 (7) | −0.0010 (8) | −0.0018 (7) |
| C29 | 0.0632 (13) | 0.0293 (9) | 0.0310 (10) | 0.0043 (9) | −0.0030 (9) | 0.0000 (8) |
| C30 | 0.0805 (17) | 0.0383 (11) | 0.0418 (12) | −0.0025 (10) | 0.0081 (11) | 0.0017 (9) |
| C31 | 0.133 (3) | 0.0419 (12) | 0.0476 (14) | −0.0040 (14) | 0.0228 (16) | 0.0059 (11) |
| C32 | 0.170 (4) | 0.0582 (17) | 0.0487 (16) | 0.028 (2) | −0.001 (2) | 0.0197 (13) |
| C33 | 0.119 (3) | 0.086 (2) | 0.0635 (18) | 0.035 (2) | −0.0273 (18) | 0.0165 (16) |
| C34 | 0.0714 (17) | 0.0604 (14) | 0.0548 (14) | 0.0069 (12) | −0.0152 (12) | 0.0078 (11) |
| C35 | 0.0615 (14) | 0.0312 (9) | 0.0346 (10) | 0.0008 (9) | 0.0086 (9) | −0.0022 (8) |
| C36 | 0.0666 (16) | 0.0621 (14) | 0.0587 (15) | 0.0074 (12) | 0.0179 (12) | 0.0076 (12) |
| C37 | 0.111 (3) | 0.093 (2) | 0.077 (2) | 0.0220 (19) | 0.053 (2) | 0.0210 (18) |
| C38 | 0.171 (4) | 0.116 (3) | 0.0408 (17) | 0.009 (3) | 0.033 (2) | 0.0017 (17) |
| C39 | 0.144 (3) | 0.137 (3) | 0.0400 (16) | −0.025 (3) | 0.0044 (18) | −0.0144 (18) |
| C40 | 0.0865 (19) | 0.0826 (18) | 0.0381 (13) | −0.0191 (15) | 0.0032 (12) | −0.0114 (12) |
top
| S1—O1 | 1.4309 (16) | S2—O4 | 1.4349 (16) |
| S1—O2 | 1.4289 (16) | S2—O5 | 1.4268 (15) |
| S1—C1 | 1.7776 (18) | S2—C21 | 1.7762 (18) |
| S1—C8 | 1.8085 (19) | S2—C28 | 1.8037 (18) |
| O3—C7 | 1.222 (2) | O6—C27 | 1.218 (2) |
| N1—C7 | 1.364 (2) | N3—C27 | 1.364 (2) |
| N1—C8 | 1.466 (2) | N3—C28 | 1.473 (2) |
| N1—C15 | 1.459 (2) | N3—C35 | 1.447 (2) |
| C1—N2 | 1.331 (2) | C21—N4 | 1.327 (2) |
| C1—C6 | 1.386 (3) | C21—C26 | 1.386 (2) |
| N2—C3 | 1.336 (3) | N4—C23 | 1.329 (2) |
| C3—H3 | 0.9300 | C23—H23 | 0.9300 |
| C3—C4 | 1.373 (3) | C23—C24 | 1.383 (3) |
| C4—H4 | 0.9300 | C24—H24 | 0.9300 |
| C4—C5 | 1.386 (3) | C24—C25 | 1.379 (3) |
| C5—H5 | 0.9300 | C25—H25 | 0.9300 |
| C5—C6 | 1.395 (2) | C25—C26 | 1.389 (2) |
| C6—C7 | 1.506 (3) | C26—C27 | 1.510 (3) |
| C8—H8 | 0.9800 | C28—H28 | 0.9800 |
| C8—C9 | 1.503 (2) | C28—C29 | 1.510 (2) |
| C9—C10 | 1.390 (3) | C29—C30 | 1.379 (3) |
| C9—C14 | 1.377 (3) | C29—C34 | 1.390 (3) |
| C10—H10 | 0.9300 | C30—H30 | 0.9300 |
| C10—C11 | 1.376 (3) | C30—C31 | 1.383 (3) |
| C11—H11 | 0.9300 | C31—H31 | 0.9300 |
| C11—C12 | 1.372 (3) | C31—C32 | 1.365 (4) |
| C12—H12 | 0.9300 | C32—H32 | 0.9300 |
| C12—C13 | 1.372 (3) | C32—C33 | 1.367 (4) |
| C13—H13 | 0.9300 | C33—H33 | 0.9300 |
| C13—C14 | 1.383 (3) | C33—C34 | 1.382 (3) |
| C14—H14 | 0.9300 | C34—H34 | 0.9300 |
| C15—C16 | 1.367 (3) | C35—C36 | 1.372 (3) |
| C15—C20 | 1.379 (3) | C35—C40 | 1.366 (3) |
| C16—H16 | 0.9300 | C36—H36 | 0.9300 |
| C16—C17 | 1.387 (3) | C36—C37 | 1.397 (4) |
| C17—H17 | 0.9300 | C37—H37 | 0.9300 |
| C17—C18 | 1.356 (4) | C37—C38 | 1.375 (5) |
| C18—H18 | 0.9300 | C38—H38 | 0.9300 |
| C18—C19 | 1.370 (4) | C38—C39 | 1.353 (5) |
| C19—H19 | 0.9300 | C39—H39 | 0.9300 |
| C19—C20 | 1.397 (3) | C39—C40 | 1.382 (4) |
| C20—H20 | 0.9300 | C40—H40 | 0.9300 |
| O1—S1—C1 | 108.86 (9) | O4—S2—C21 | 108.44 (8) |
| O1—S1—C8 | 111.01 (9) | O4—S2—C28 | 111.03 (9) |
| O2—S1—O1 | 119.48 (10) | O5—S2—O4 | 119.14 (10) |
| O2—S1—C1 | 109.82 (9) | O5—S2—C21 | 109.50 (9) |
| O2—S1—C8 | 108.66 (9) | O5—S2—C28 | 108.74 (9) |
| C1—S1—C8 | 96.59 (8) | C21—S2—C28 | 97.89 (8) |
| C7—N1—C8 | 119.92 (15) | C27—N3—C28 | 120.15 (15) |
| C7—N1—C15 | 118.80 (14) | C27—N3—C35 | 118.72 (14) |
| C15—N1—C8 | 119.39 (13) | C35—N3—C28 | 118.90 (14) |
| N2—C1—S1 | 116.15 (14) | N4—C21—S2 | 115.57 (13) |
| N2—C1—C6 | 126.13 (17) | N4—C21—C26 | 126.60 (16) |
| C6—C1—S1 | 117.72 (14) | C26—C21—S2 | 117.81 (14) |
| C1—N2—C3 | 115.68 (18) | C21—N4—C23 | 115.95 (16) |
| N2—C3—H3 | 118.0 | N4—C23—H23 | 118.4 |
| N2—C3—C4 | 123.90 (19) | N4—C23—C24 | 123.15 (19) |
| C4—C3—H3 | 118.0 | C24—C23—H23 | 118.4 |
| C3—C4—H4 | 120.5 | C23—C24—H24 | 120.4 |
| C3—C4—C5 | 119.07 (18) | C25—C24—C23 | 119.26 (17) |
| C5—C4—H4 | 120.5 | C25—C24—H24 | 120.4 |
| C4—C5—H5 | 120.5 | C24—C25—H25 | 120.3 |
| C4—C5—C6 | 118.94 (19) | C24—C25—C26 | 119.32 (17) |
| C6—C5—H5 | 120.5 | C26—C25—H25 | 120.3 |
| C1—C6—C5 | 116.27 (17) | C21—C26—C25 | 115.71 (17) |
| C1—C6—C7 | 125.04 (15) | C21—C26—C27 | 124.67 (15) |
| C5—C6—C7 | 118.58 (16) | C25—C26—C27 | 119.46 (16) |
| O3—C7—N1 | 122.41 (17) | O6—C27—N3 | 122.22 (17) |
| O3—C7—C6 | 119.79 (15) | O6—C27—C26 | 119.29 (16) |
| N1—C7—C6 | 117.77 (15) | N3—C27—C26 | 118.39 (15) |
| S1—C8—H8 | 107.5 | S2—C28—H28 | 107.6 |
| N1—C8—S1 | 108.82 (12) | N3—C28—S2 | 107.80 (12) |
| N1—C8—H8 | 107.5 | N3—C28—H28 | 107.6 |
| N1—C8—C9 | 115.31 (14) | N3—C28—C29 | 115.84 (15) |
| C9—C8—S1 | 109.85 (12) | C29—C28—S2 | 110.23 (12) |
| C9—C8—H8 | 107.5 | C29—C28—H28 | 107.6 |
| C10—C9—C8 | 122.03 (16) | C30—C29—C28 | 123.24 (19) |
| C14—C9—C8 | 118.21 (16) | C30—C29—C34 | 119.20 (19) |
| C14—C9—C10 | 119.72 (17) | C34—C29—C28 | 117.46 (19) |
| C9—C10—H10 | 120.1 | C29—C30—H30 | 119.9 |
| C11—C10—C9 | 119.8 (2) | C29—C30—C31 | 120.2 (2) |
| C11—C10—H10 | 120.1 | C31—C30—H30 | 119.9 |
| C10—C11—H11 | 119.8 | C30—C31—H31 | 119.8 |
| C12—C11—C10 | 120.4 (2) | C32—C31—C30 | 120.3 (3) |
| C12—C11—H11 | 119.8 | C32—C31—H31 | 119.8 |
| C11—C12—H12 | 120.0 | C31—C32—H32 | 119.9 |
| C11—C12—C13 | 120.03 (19) | C31—C32—C33 | 120.1 (3) |
| C13—C12—H12 | 120.0 | C33—C32—H32 | 119.9 |
| C12—C13—H13 | 119.9 | C32—C33—H33 | 119.8 |
| C12—C13—C14 | 120.3 (2) | C32—C33—C34 | 120.4 (3) |
| C14—C13—H13 | 119.9 | C34—C33—H33 | 119.8 |
| C9—C14—C13 | 119.8 (2) | C29—C34—H34 | 120.1 |
| C9—C14—H14 | 120.1 | C33—C34—C29 | 119.8 (3) |
| C13—C14—H14 | 120.1 | C33—C34—H34 | 120.1 |
| C16—C15—N1 | 119.61 (18) | C36—C35—N3 | 119.09 (19) |
| C16—C15—C20 | 120.9 (2) | C40—C35—N3 | 119.53 (19) |
| C20—C15—N1 | 119.38 (18) | C40—C35—C36 | 121.4 (2) |
| C15—C16—H16 | 120.4 | C35—C36—H36 | 120.6 |
| C15—C16—C17 | 119.2 (2) | C35—C36—C37 | 118.7 (3) |
| C17—C16—H16 | 120.4 | C37—C36—H36 | 120.6 |
| C16—C17—H17 | 119.7 | C36—C37—H37 | 120.2 |
| C18—C17—C16 | 120.6 (3) | C38—C37—C36 | 119.6 (3) |
| C18—C17—H17 | 119.7 | C38—C37—H37 | 120.2 |
| C17—C18—H18 | 119.7 | C37—C38—H38 | 119.8 |
| C17—C18—C19 | 120.5 (2) | C39—C38—C37 | 120.4 (3) |
| C19—C18—H18 | 119.7 | C39—C38—H38 | 119.8 |
| C18—C19—H19 | 120.1 | C38—C39—H39 | 119.6 |
| C18—C19—C20 | 119.8 (3) | C38—C39—C40 | 120.8 (3) |
| C20—C19—H19 | 120.1 | C40—C39—H39 | 119.6 |
| C15—C20—C19 | 118.9 (2) | C35—C40—C39 | 119.0 (3) |
| C15—C20—H20 | 120.5 | C35—C40—H40 | 120.5 |
| C19—C20—H20 | 120.5 | C39—C40—H40 | 120.5 |
| S1—C1—N2—C3 | 179.14 (15) | S2—C21—N4—C23 | 177.70 (14) |
| S1—C1—C6—C5 | −179.38 (14) | S2—C21—C26—C25 | −178.19 (14) |
| S1—C1—C6—C7 | 4.6 (3) | S2—C21—C26—C27 | −2.7 (2) |
| S1—C8—C9—C10 | 64.1 (2) | S2—C28—C29—C30 | −56.3 (2) |
| S1—C8—C9—C14 | −113.40 (17) | S2—C28—C29—C34 | 119.99 (18) |
| O1—S1—C1—N2 | 97.46 (17) | O4—S2—C21—N4 | −95.33 (16) |
| O1—S1—C1—C6 | −82.47 (16) | O4—S2—C21—C26 | 82.93 (16) |
| O1—S1—C8—N1 | 52.60 (14) | O4—S2—C28—N3 | −53.75 (14) |
| O1—S1—C8—C9 | −74.51 (14) | O4—S2—C28—C29 | 73.56 (15) |
| O2—S1—C1—N2 | −35.07 (19) | O5—S2—C21—N4 | 36.17 (18) |
| O2—S1—C1—C6 | 145.00 (15) | O5—S2—C21—C26 | −145.57 (15) |
| O2—S1—C8—N1 | −174.07 (12) | O5—S2—C28—N3 | 173.30 (12) |
| O2—S1—C8—C9 | 58.82 (15) | O5—S2—C28—C29 | −59.39 (16) |
| N1—C8—C9—C10 | −59.3 (2) | N3—C28—C29—C30 | 66.4 (2) |
| N1—C8—C9—C14 | 123.22 (18) | N3—C28—C29—C34 | −117.3 (2) |
| N1—C15—C16—C17 | 174.64 (19) | N3—C35—C36—C37 | 176.9 (2) |
| N1—C15—C20—C19 | −175.11 (19) | N3—C35—C40—C39 | −177.0 (2) |
| C1—S1—C8—N1 | −60.54 (13) | C21—S2—C28—N3 | 59.54 (13) |
| C1—S1—C8—C9 | 172.35 (13) | C21—S2—C28—C29 | −173.14 (14) |
| C1—N2—C3—C4 | 0.1 (3) | C21—N4—C23—C24 | 0.9 (3) |
| C1—C6—C7—O3 | 157.04 (18) | C21—C26—C27—O6 | −159.73 (18) |
| C1—C6—C7—N1 | −20.8 (3) | C21—C26—C27—N3 | 16.7 (3) |
| N2—C1—C6—C5 | 0.7 (3) | N4—C21—C26—C25 | −0.1 (3) |
| N2—C1—C6—C7 | −175.37 (18) | N4—C21—C26—C27 | 175.31 (18) |
| N2—C3—C4—C5 | 0.9 (3) | N4—C23—C24—C25 | −0.9 (3) |
| C3—C4—C5—C6 | −1.1 (3) | C23—C24—C25—C26 | 0.4 (3) |
| C4—C5—C6—C1 | 0.4 (3) | C24—C25—C26—C21 | 0.1 (3) |
| C4—C5—C6—C7 | 176.70 (17) | C24—C25—C26—C27 | −175.55 (17) |
| C5—C6—C7—O3 | −18.9 (3) | C25—C26—C27—O6 | 15.6 (3) |
| C5—C6—C7—N1 | 163.18 (16) | C25—C26—C27—N3 | −167.98 (16) |
| C6—C1—N2—C3 | −0.9 (3) | C26—C21—N4—C23 | −0.4 (3) |
| C7—N1—C8—S1 | 57.44 (18) | C27—N3—C28—S2 | −58.41 (19) |
| C7—N1—C8—C9 | −178.63 (15) | C27—N3—C28—C29 | 177.60 (16) |
| C7—N1—C15—C16 | 99.0 (2) | C27—N3—C35—C36 | 89.0 (2) |
| C7—N1—C15—C20 | −84.2 (2) | C27—N3—C35—C40 | −92.1 (2) |
| C8—S1—C1—N2 | −147.65 (16) | C28—S2—C21—N4 | 149.32 (15) |
| C8—S1—C1—C6 | 32.42 (16) | C28—S2—C21—C26 | −32.42 (16) |
| C8—N1—C7—O3 | 167.93 (17) | C28—N3—C27—O6 | −165.63 (17) |
| C8—N1—C7—C6 | −14.3 (2) | C28—N3—C27—C26 | 18.0 (2) |
| C8—N1—C15—C16 | −65.4 (2) | C28—N3—C35—C36 | −107.9 (2) |
| C8—N1—C15—C20 | 111.5 (2) | C28—N3—C35—C40 | 70.9 (2) |
| C8—C9—C10—C11 | −178.63 (18) | C28—C29—C30—C31 | 175.96 (19) |
| C8—C9—C14—C13 | 178.46 (19) | C28—C29—C34—C33 | −176.8 (2) |
| C9—C10—C11—C12 | 0.7 (3) | C29—C30—C31—C32 | 0.6 (4) |
| C10—C9—C14—C13 | 0.9 (3) | C30—C29—C34—C33 | −0.4 (3) |
| C10—C11—C12—C13 | 0.0 (3) | C30—C31—C32—C33 | −0.2 (4) |
| C11—C12—C13—C14 | −0.3 (4) | C31—C32—C33—C34 | −0.4 (5) |
| C12—C13—C14—C9 | −0.2 (3) | C32—C33—C34—C29 | 0.7 (4) |
| C14—C9—C10—C11 | −1.2 (3) | C34—C29—C30—C31 | −0.3 (3) |
| C15—N1—C7—O3 | 3.7 (3) | C35—N3—C27—O6 | −2.8 (3) |
| C15—N1—C7—C6 | −178.52 (15) | C35—N3—C27—C26 | −179.13 (16) |
| C15—N1—C8—S1 | −138.38 (14) | C35—N3—C28—S2 | 138.78 (14) |
| C15—N1—C8—C9 | −14.5 (2) | C35—N3—C28—C29 | 14.8 (2) |
| C15—C16—C17—C18 | 1.1 (4) | C35—C36—C37—C38 | 0.3 (4) |
| C16—C15—C20—C19 | 1.7 (3) | C36—C35—C40—C39 | 1.9 (4) |
| C16—C17—C18—C19 | 0.4 (4) | C36—C37—C38—C39 | 1.3 (5) |
| C17—C18—C19—C20 | −0.9 (4) | C37—C38—C39—C40 | −1.4 (6) |
| C18—C19—C20—C15 | −0.2 (3) | C38—C39—C40—C35 | −0.2 (5) |
| C20—C15—C16—C17 | −2.2 (3) | C40—C35—C36—C37 | −1.9 (3) |
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| D—H···A | D—H | H···A | D···A | D—H···A |
| C3—H3···O5i | 0.93 | 2.56 | 3.234 (3) | 130 |
| C5—H5···O4ii | 0.93 | 2.69 | 3.388 (2) | 132 |
| C8—H8···O6ii | 0.98 | 2.31 | 3.089 (2) | 136 |
| C16—H16···O6ii | 0.93 | 2.71 | 3.466 (3) | 139 |
| C20—H20···O6 | 0.93 | 2.70 | 3.496 (3) | 145 |
| C25—H25···O1 | 0.93 | 2.75 | 3.463 (3) | 135 |
| C28—H28···O3 | 0.98 | 2.37 | 3.126 (2) | 134 |
| C36—H36···O3iii | 0.93 | 2.64 | 3.381 (3) | 137 |
| C40—H40···O3 | 0.93 | 2.68 | 3.439 (3) | 140 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, y, z.
![Crystal structures of the sulfones of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2,3-diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one (2024)](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAQAAAC1HAwCAAAAC0lEQVR42mP8/h8AAvMB+NzmkbcAAAAASUVORK5CYII=)