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In the title compound, C30H31NO3S2, the piperidine ring adopts a distorted chair conformation. The thio­phene rings have twisted conformations about the C—C bonds. The mean plane of the piperidine ring makes a near orthogonal conformation with the toluene ring. Two of the phenyl rings in the structure are positionally disordered over two sets of sites with occupancies of 0.56 (2)/0.44 (2) and 0.672 (16)/0.328 (16). A region of disordered electron density was corrected for using the SQUEEZE [Spek (2015). Acta Cryst. C71, 9–18] routine in PLATON. The given chemical formula and other crystal data do not take into account the unknown solvent mol­ecule. In the crystal, O—H...O hydrogen bonds are observed along with intra­molecular S...H, O...H, C...H and H...H contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314621002108/bv4035sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314621002108/bv4035Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314621002108/bv4035Isup3.cml
Supplementary material

CCDC reference: 2064599

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.043
  • wR factor = 0.110
  • Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C NonSolvent Resd 1 C Ueq(max)/Ueq(min) Range 3.1 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00424 Ang. PLAT707_ALERT_1_C D...A Calc 2.855(3), Rep 2.851(3), Dev.. 1.33 Sigma O3 -O3 1.555 3.466 ........ # 96 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 2 Report
Alert level G PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 24 Report PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report PLAT014_ALERT_1_G N.O.K. _shelx_fab_checksum Found in CIF ...... Please Check PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records 2 Report PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records 2 Report PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 33% Note PLAT605_ALERT_4_G Largest Solvent Accessible VOID in the Structure 294 A   3 PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 5 Note PLAT792_ALERT_1_G Model has Chirality at C9 (Polar SPGR) S Verify PLAT792_ALERT_1_G Model has Chirality at C10 (Polar SPGR) S Verify PLAT792_ALERT_1_G Model has Chirality at C13 (Polar SPGR) R Verify PLAT792_ALERT_1_G Model has Chirality at C15 (Polar SPGR) R Verify PLAT792_ALERT_1_G Model has Chirality at C17 (Polar SPGR) R Verify PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms .... ! Info PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 408 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 2 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 1 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 4 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 9 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 21 ALERT level G = General information/check it is not something unexpected 9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Qmol (Gans & Shalloway, 2001); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015) and PLATON (Spek, 2020)'.

13-Benzyl-4,11-dihydroxy-1,8-diphenyl-2,9-dithia-13-azadispiro[4.1.4.3]tetradecan-6-one top
Crystal data top
C30H31NO3S2Melting point: 476.15 K
Mr = 517.68Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P421cCell parameters from 6903 reflections
a = 25.3750 (4) Åθ = 1.1–28.3°
c = 8.6456 (2) ŵ = 0.22 mm1
V = 5566.8 (2) Å3T = 293 K
Z = 8Block, colourless
F(000) = 21920.28 × 0.24 × 0.20 mm
Dx = 1.235 Mg m3
Data collection top
Bruker SMART APEXII area-detector
diffractometer
5681 reflections with I > 2σ(I)
ω and φ scansRint = 0.033
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
θmax = 28.3°, θmin = 1.8°
Tmin = 0.685, Tmax = 0.742h = 3323
30401 measured reflectionsk = 3327
6899 independent reflectionsl = 1111
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0659P)2 + 0.1922P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
6899 reflectionsΔρmax = 0.27 e Å3
389 parametersΔρmin = 0.15 e Å3
408 restraintsAbsolute structure: Flack x determined using 2151 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.04 (2)
Special details top

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.

Refinement. The hydroxy H atoms were refined as riding: O—H = 0.82 Å with Uiso(H) = 1.5Ueq(O)·. The C-bound H atoms were included in calculated positions and treated as riding, with C—H = 0.95–0.98 Å, and with 1.2Ueq(C) for H atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.19875 (3)0.80219 (4)0.82727 (10)0.0581 (2)
S20.07519 (3)0.97740 (3)0.14696 (9)0.04708 (19)
N0.13618 (9)0.81533 (8)0.3251 (2)0.0365 (5)
O10.10182 (9)0.88166 (9)0.7697 (2)0.0528 (5)
H10.0839270.9032370.7225510.079*
O20.17096 (8)0.94891 (7)0.5606 (2)0.0440 (5)
O30.05248 (7)0.94022 (8)0.4969 (2)0.0414 (4)
H30.0205310.9391590.5107860.062*
C10.2681 (4)0.8548 (5)0.6236 (10)0.043 (3)0.44 (2)
C20.3011 (6)0.8117 (5)0.6461 (15)0.051 (2)0.44 (2)
H2A0.2897870.7834220.7059440.061*0.44 (2)
C30.3509 (6)0.8109 (5)0.5791 (16)0.065 (2)0.44 (2)
H3A0.3728920.7820490.5941520.078*0.44 (2)
C40.3677 (4)0.8532 (5)0.4897 (13)0.074 (2)0.44 (2)
H4A0.4010380.8526160.4448620.089*0.44 (2)
C50.3348 (5)0.8963 (5)0.4672 (18)0.067 (2)0.44 (2)
H5A0.3460800.9245560.4073630.081*0.44 (2)
C60.2850 (4)0.8971 (5)0.5342 (17)0.057 (2)0.44 (2)
H6A0.2629740.9259310.5191550.068*0.44 (2)
C1A0.2679 (3)0.8540 (4)0.6274 (8)0.0401 (19)0.56 (2)
C2A0.2951 (4)0.8070 (3)0.6069 (13)0.0478 (18)0.56 (2)
H2AA0.2790470.7751470.6319210.057*0.56 (2)
C3A0.3462 (4)0.8075 (3)0.5489 (12)0.066 (2)0.56 (2)
H3AA0.3643290.7760200.5352250.079*0.56 (2)
C4A0.3701 (3)0.8551 (4)0.5115 (11)0.079 (2)0.56 (2)
H4AA0.4043020.8554440.4727470.094*0.56 (2)
C5A0.3430 (4)0.9022 (4)0.5320 (17)0.072 (2)0.56 (2)
H5AA0.3589930.9339960.5069640.087*0.56 (2)
C6A0.2919 (3)0.9016 (3)0.5899 (14)0.0524 (18)0.56 (2)
H6AA0.2737110.9331240.6036600.063*0.56 (2)
C70.21172 (10)0.85613 (11)0.6917 (3)0.0370 (6)
H70.2081630.8891840.7493870.044*
C80.13063 (12)0.79323 (13)0.7676 (4)0.0495 (7)
H8A0.1268730.7609350.7086000.059*
H8B0.1077570.7912980.8573220.059*
C90.11644 (10)0.84041 (10)0.6689 (3)0.0381 (6)
H90.0869700.8315990.6003580.046*
C100.16622 (10)0.85436 (10)0.5712 (3)0.0319 (5)
C110.17586 (11)0.81241 (10)0.4471 (3)0.0380 (6)
H11A0.2105650.8174500.4024540.046*
H11B0.1749080.7777340.4942230.046*
C120.14383 (11)0.86442 (10)0.2399 (3)0.0381 (6)
H12A0.1230680.8639100.1456870.046*
H12B0.1806340.8682700.2118070.046*
C130.12668 (9)0.91073 (9)0.3422 (3)0.0314 (5)
C140.15673 (9)0.90880 (10)0.4977 (3)0.0315 (5)
C150.06627 (10)0.90622 (10)0.3714 (3)0.0352 (5)
H150.0572080.8697490.3975430.042*
C160.03912 (11)0.92192 (12)0.2229 (4)0.0457 (7)
H16A0.0027800.9316430.2428980.055*
H16B0.0395380.8929390.1497580.055*
C170.13408 (10)0.96560 (10)0.2640 (3)0.0350 (5)
H170.1337540.9918420.3471270.042*
C180.18491 (10)0.97408 (9)0.1735 (3)0.0374 (5)
C190.22921 (12)0.99325 (12)0.2497 (4)0.0505 (7)
H190.2279040.9988130.3559360.061*
C200.27490 (14)1.00411 (13)0.1705 (5)0.0645 (9)
H200.3041601.0167100.2236580.077*
C210.27770 (16)0.99650 (13)0.0129 (5)0.0681 (10)
H210.3085181.0041570.0407640.082*
C220.23375 (16)0.97718 (14)0.0645 (4)0.0664 (10)
H220.2351720.9720660.1709560.080*
C230.18816 (13)0.96554 (12)0.0146 (3)0.0499 (7)
H230.1593200.9518880.0383610.060*
C240.13841 (13)0.76884 (11)0.2234 (3)0.0473 (7)
H24A0.1741110.7641420.1856640.057*
H24B0.1155470.7742370.1348570.057*
C250.1210 (3)0.71931 (18)0.3115 (8)0.0449 (15)0.672 (16)
C260.0695 (2)0.7125 (3)0.3626 (11)0.0587 (17)0.672 (16)
H26A0.0443910.7384010.3433790.070*0.672 (16)
C270.0556 (2)0.6671 (3)0.4425 (10)0.086 (2)0.672 (16)
H27A0.0211070.6625410.4766610.103*0.672 (16)
C280.0931 (4)0.6284 (2)0.4712 (9)0.097 (2)0.672 (16)
H28A0.0837650.5979970.5246300.116*0.672 (16)
C290.1446 (3)0.6352 (2)0.4201 (10)0.089 (2)0.672 (16)
H29A0.1697080.6093120.4393170.106*0.672 (16)
C300.1585 (3)0.6806 (2)0.3402 (9)0.0669 (17)0.672 (16)
H30A0.1929930.6851720.3060330.080*0.672 (16)
C25A0.1208 (6)0.7211 (4)0.2988 (18)0.048 (3)0.328 (16)
C26A0.0731 (6)0.7254 (5)0.377 (2)0.054 (3)0.328 (16)
H26B0.0562430.7578230.3837670.065*0.328 (16)
C27A0.0508 (5)0.6812 (6)0.446 (2)0.080 (3)0.328 (16)
H27B0.0189550.6841080.4987500.096*0.328 (16)
C28A0.0761 (6)0.6327 (5)0.4366 (19)0.089 (3)0.328 (16)
H28B0.0611290.6031720.4827180.106*0.328 (16)
C29A0.1237 (7)0.6284 (4)0.358 (2)0.086 (3)0.328 (16)
H29B0.1405920.5959500.3517040.103*0.328 (16)
C30A0.1460 (5)0.6726 (5)0.2892 (19)0.069 (3)0.328 (16)
H30B0.1778820.6696650.2367200.083*0.328 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0511 (4)0.0731 (5)0.0502 (4)0.0028 (4)0.0115 (4)0.0292 (4)
S20.0453 (4)0.0521 (4)0.0438 (4)0.0018 (3)0.0063 (3)0.0186 (3)
N0.0486 (12)0.0305 (10)0.0305 (11)0.0012 (9)0.0034 (10)0.0029 (9)
O10.0582 (13)0.0577 (13)0.0424 (11)0.0094 (10)0.0105 (10)0.0008 (10)
O20.0581 (12)0.0362 (10)0.0377 (10)0.0013 (8)0.0104 (9)0.0039 (8)
O30.0374 (10)0.0483 (11)0.0386 (10)0.0014 (8)0.0034 (8)0.0008 (9)
C10.039 (5)0.044 (5)0.046 (5)0.005 (4)0.009 (4)0.001 (4)
C20.046 (4)0.045 (4)0.060 (5)0.002 (3)0.010 (4)0.003 (4)
C30.047 (4)0.065 (4)0.084 (5)0.011 (4)0.000 (4)0.004 (4)
C40.051 (4)0.080 (5)0.091 (5)0.006 (4)0.016 (4)0.000 (4)
C50.054 (4)0.072 (4)0.076 (6)0.002 (3)0.009 (5)0.009 (5)
C60.049 (4)0.053 (4)0.068 (6)0.005 (3)0.006 (4)0.013 (4)
C1A0.037 (4)0.043 (4)0.040 (4)0.002 (3)0.006 (3)0.002 (3)
C2A0.043 (3)0.049 (3)0.051 (4)0.002 (2)0.013 (3)0.008 (3)
C3A0.050 (3)0.065 (4)0.081 (4)0.016 (3)0.005 (3)0.012 (3)
C4A0.049 (4)0.084 (4)0.102 (5)0.007 (3)0.019 (4)0.004 (4)
C5A0.052 (4)0.072 (4)0.092 (6)0.001 (3)0.014 (4)0.016 (4)
C6A0.047 (3)0.048 (3)0.062 (5)0.009 (3)0.003 (3)0.010 (3)
C70.0398 (13)0.0405 (13)0.0308 (13)0.0000 (11)0.0042 (10)0.0058 (11)
C80.0467 (16)0.0555 (17)0.0464 (16)0.0029 (13)0.0034 (13)0.0175 (14)
C90.0404 (13)0.0428 (13)0.0310 (13)0.0013 (11)0.0000 (11)0.0049 (12)
C100.0346 (12)0.0328 (12)0.0282 (12)0.0003 (9)0.0023 (10)0.0027 (10)
C110.0426 (14)0.0332 (13)0.0382 (13)0.0037 (10)0.0015 (11)0.0006 (11)
C120.0484 (15)0.0357 (13)0.0302 (12)0.0013 (11)0.0003 (12)0.0004 (11)
C130.0350 (12)0.0318 (11)0.0272 (11)0.0003 (9)0.0006 (10)0.0029 (10)
C140.0319 (12)0.0372 (13)0.0254 (11)0.0021 (10)0.0012 (10)0.0013 (10)
C150.0355 (13)0.0378 (13)0.0324 (13)0.0028 (10)0.0025 (11)0.0040 (11)
C160.0442 (15)0.0496 (16)0.0432 (16)0.0022 (12)0.0107 (12)0.0070 (13)
C170.0396 (13)0.0340 (12)0.0313 (12)0.0015 (10)0.0037 (11)0.0042 (10)
C180.0454 (14)0.0285 (12)0.0383 (13)0.0009 (10)0.0030 (11)0.0043 (11)
C190.0462 (16)0.0539 (17)0.0514 (17)0.0058 (13)0.0004 (14)0.0103 (15)
C200.0486 (18)0.061 (2)0.084 (3)0.0088 (15)0.0008 (19)0.0099 (19)
C210.066 (2)0.0541 (19)0.085 (3)0.0054 (16)0.038 (2)0.0046 (19)
C220.089 (3)0.0534 (19)0.057 (2)0.0153 (18)0.031 (2)0.0065 (17)
C230.0624 (18)0.0438 (15)0.0436 (16)0.0117 (13)0.0110 (14)0.0027 (13)
C240.0670 (19)0.0379 (14)0.0370 (15)0.0026 (13)0.0065 (14)0.0078 (12)
C250.053 (3)0.034 (3)0.047 (3)0.006 (2)0.001 (3)0.007 (2)
C260.054 (3)0.042 (3)0.081 (4)0.009 (3)0.001 (3)0.001 (3)
C270.089 (4)0.060 (5)0.110 (4)0.021 (3)0.024 (4)0.008 (4)
C280.127 (5)0.055 (3)0.109 (5)0.014 (4)0.004 (4)0.023 (3)
C290.109 (5)0.045 (3)0.112 (5)0.014 (3)0.017 (4)0.005 (3)
C300.071 (3)0.041 (3)0.089 (4)0.004 (2)0.003 (3)0.009 (3)
C25A0.055 (5)0.033 (5)0.056 (5)0.003 (5)0.005 (5)0.009 (5)
C26A0.061 (5)0.033 (5)0.070 (5)0.018 (4)0.004 (4)0.008 (5)
C27A0.089 (5)0.046 (6)0.106 (6)0.014 (4)0.016 (5)0.005 (5)
C28A0.105 (6)0.050 (5)0.111 (6)0.012 (5)0.007 (5)0.024 (5)
C29A0.102 (6)0.038 (4)0.117 (7)0.006 (5)0.007 (6)0.008 (5)
C30A0.073 (5)0.036 (4)0.098 (6)0.002 (4)0.002 (5)0.011 (5)
Geometric parameters (Å, º) top
S1—C81.818 (3)C12—H12A0.9700
S1—C71.832 (3)C12—H12B0.9700
S2—C161.803 (3)C13—C141.546 (3)
S2—C171.829 (3)C13—C151.558 (3)
N—C111.460 (3)C13—C171.559 (3)
N—C121.460 (3)C15—C161.511 (4)
N—C241.473 (3)C15—H150.9800
O1—C91.412 (3)C16—H16A0.9700
O1—H10.8200C16—H16B0.9700
O2—C141.209 (3)C17—C181.524 (4)
O3—C151.430 (3)C17—H170.9800
O3—H30.8200C18—C191.390 (4)
C1—C21.3900C18—C231.394 (4)
C1—C61.3900C19—C201.374 (5)
C1—C71.548 (10)C19—H190.9300
C2—C31.3900C20—C211.377 (6)
C2—H2A0.9300C20—H200.9300
C3—C41.3900C21—C221.390 (6)
C3—H3A0.9300C21—H210.9300
C4—C51.3900C22—C231.376 (5)
C4—H4A0.9300C22—H220.9300
C5—C61.3900C23—H230.9300
C5—H5A0.9300C24—C25A1.448 (10)
C6—H6A0.9300C24—C251.535 (6)
C1A—C2A1.3900C24—H24A0.9700
C1A—C6A1.3900C24—H24B0.9700
C1A—C71.532 (8)C25—C261.3900
C2A—C3A1.3900C25—C301.3900
C2A—H2AA0.9300C26—C271.3900
C3A—C4A1.3900C26—H26A0.9300
C3A—H3AA0.9300C27—C281.3900
C4A—C5A1.3900C27—H27A0.9300
C4A—H4AA0.9300C28—C291.3900
C5A—C6A1.3900C28—H28A0.9300
C5A—H5AA0.9300C29—C301.3900
C6A—H6AA0.9300C29—H29A0.9300
C7—C101.556 (3)C30—H30A0.9300
C7—H70.9800C25A—C26A1.3900
C8—C91.514 (4)C25A—C30A1.3900
C8—H8A0.9700C26A—C27A1.3900
C8—H8B0.9700C26A—H26B0.9300
C9—C101.560 (4)C27A—C28A1.3900
C9—H90.9800C27A—H27B0.9300
C10—C111.531 (3)C28A—C29A1.3900
C10—C141.540 (3)C28A—H28B0.9300
C11—H11A0.9700C29A—C30A1.3900
C11—H11B0.9700C29A—H29B0.9300
C12—C131.534 (4)C30A—H30B0.9300
C8—S1—C794.74 (12)C14—C13—C17110.24 (19)
C16—S2—C1794.91 (12)C15—C13—C17104.74 (19)
C11—N—C12108.4 (2)O2—C14—C10121.5 (2)
C11—N—C24111.4 (2)O2—C14—C13120.8 (2)
C12—N—C24112.1 (2)C10—C14—C13117.7 (2)
C9—O1—H1109.5O3—C15—C16112.0 (2)
C15—O3—H3109.5O3—C15—C13108.7 (2)
C2—C1—C6120.0C16—C15—C13106.9 (2)
C2—C1—C7121.3 (8)O3—C15—H15109.7
C6—C1—C7118.6 (8)C16—C15—H15109.7
C3—C2—C1120.0C13—C15—H15109.7
C3—C2—H2A120.0C15—C16—S2106.49 (19)
C1—C2—H2A120.0C15—C16—H16A110.4
C4—C3—C2120.0S2—C16—H16A110.4
C4—C3—H3A120.0C15—C16—H16B110.4
C2—C3—H3A120.0S2—C16—H16B110.4
C3—C4—C5120.0H16A—C16—H16B108.6
C3—C4—H4A120.0C18—C17—C13116.8 (2)
C5—C4—H4A120.0C18—C17—S2112.63 (18)
C6—C5—C4120.0C13—C17—S2106.71 (16)
C6—C5—H5A120.0C18—C17—H17106.7
C4—C5—H5A120.0C13—C17—H17106.7
C5—C6—C1120.0S2—C17—H17106.7
C5—C6—H6A120.0C19—C18—C23118.3 (3)
C1—C6—H6A120.0C19—C18—C17119.4 (2)
C2A—C1A—C6A120.0C23—C18—C17122.3 (3)
C2A—C1A—C7122.5 (6)C20—C19—C18121.1 (3)
C6A—C1A—C7117.5 (6)C20—C19—H19119.5
C1A—C2A—C3A120.0C18—C19—H19119.5
C1A—C2A—H2AA120.0C19—C20—C21120.5 (3)
C3A—C2A—H2AA120.0C19—C20—H20119.7
C4A—C3A—C2A120.0C21—C20—H20119.7
C4A—C3A—H3AA120.0C20—C21—C22119.0 (3)
C2A—C3A—H3AA120.0C20—C21—H21120.5
C3A—C4A—C5A120.0C22—C21—H21120.5
C3A—C4A—H4AA120.0C23—C22—C21120.7 (3)
C5A—C4A—H4AA120.0C23—C22—H22119.6
C4A—C5A—C6A120.0C21—C22—H22119.6
C4A—C5A—H5AA120.0C22—C23—C18120.4 (3)
C6A—C5A—H5AA120.0C22—C23—H23119.8
C5A—C6A—C1A120.0C18—C23—H23119.8
C5A—C6A—H6AA120.0C25A—C24—N112.9 (6)
C1A—C6A—H6AA120.0N—C24—C25110.4 (3)
C1A—C7—C10116.6 (3)N—C24—H24A109.6
C1—C7—C10115.5 (4)C25—C24—H24A109.6
C1A—C7—S1111.9 (4)N—C24—H24B109.6
C1—C7—S1113.1 (5)C25—C24—H24B109.6
C10—C7—S1105.87 (16)H24A—C24—H24B108.1
C1—C7—H7107.3C26—C25—C30120.0
C10—C7—H7107.3C26—C25—C24122.0 (4)
S1—C7—H7107.3C30—C25—C24118.0 (4)
C9—C8—S1106.7 (2)C27—C26—C25120.0
C9—C8—H8A110.4C27—C26—H26A120.0
S1—C8—H8A110.4C25—C26—H26A120.0
C9—C8—H8B110.4C26—C27—C28120.0
S1—C8—H8B110.4C26—C27—H27A120.0
H8A—C8—H8B108.6C28—C27—H27A120.0
O1—C9—C8107.5 (2)C27—C28—C29120.0
O1—C9—C10112.3 (2)C27—C28—H28A120.0
C8—C9—C10107.0 (2)C29—C28—H28A120.0
O1—C9—H9110.0C30—C29—C28120.0
C8—C9—H9110.0C30—C29—H29A120.0
C10—C9—H9110.0C28—C29—H29A120.0
C11—C10—C14111.0 (2)C29—C30—C25120.0
C11—C10—C7111.8 (2)C29—C30—H30A120.0
C14—C10—C7111.51 (19)C25—C30—H30A120.0
C11—C10—C9110.5 (2)C26A—C25A—C30A120.0
C14—C10—C9107.49 (19)C26A—C25A—C24115.0 (10)
C7—C10—C9104.2 (2)C30A—C25A—C24124.9 (10)
N—C11—C10111.2 (2)C25A—C26A—C27A120.0
N—C11—H11A109.4C25A—C26A—H26B120.0
C10—C11—H11A109.4C27A—C26A—H26B120.0
N—C11—H11B109.4C26A—C27A—C28A120.0
C10—C11—H11B109.4C26A—C27A—H27B120.0
H11A—C11—H11B108.0C28A—C27A—H27B120.0
N—C12—C13109.0 (2)C29A—C28A—C27A120.0
N—C12—H12A109.9C29A—C28A—H28B120.0
C13—C12—H12A109.9C27A—C28A—H28B120.0
N—C12—H12B109.9C28A—C29A—C30A120.0
C13—C12—H12B109.9C28A—C29A—H29B120.0
H12A—C12—H12B108.3C30A—C29A—H29B120.0
C12—C13—C14109.70 (19)C29A—C30A—C25A120.0
C12—C13—C15108.5 (2)C29A—C30A—H30B120.0
C14—C13—C15109.98 (19)C25A—C30A—H30B120.0
C12—C13—C17113.6 (2)
C6—C1—C2—C30.0C9—C10—C14—C1385.9 (2)
C7—C1—C2—C3177.8 (7)C12—C13—C14—O2143.1 (2)
C1—C2—C3—C40.0C15—C13—C14—O297.7 (3)
C2—C3—C4—C50.0C17—C13—C14—O217.3 (3)
C3—C4—C5—C60.0C12—C13—C14—C1038.7 (3)
C4—C5—C6—C10.0C15—C13—C14—C1080.5 (2)
C2—C1—C6—C50.0C17—C13—C14—C10164.5 (2)
C7—C1—C6—C5177.8 (7)C12—C13—C15—O3165.0 (2)
C6A—C1A—C2A—C3A0.0C14—C13—C15—O345.1 (3)
C7—C1A—C2A—C3A179.6 (6)C17—C13—C15—O373.4 (2)
C1A—C2A—C3A—C4A0.0C12—C13—C15—C1674.0 (3)
C2A—C3A—C4A—C5A0.0C14—C13—C15—C16166.1 (2)
C3A—C4A—C5A—C6A0.0C17—C13—C15—C1647.6 (3)
C4A—C5A—C6A—C1A0.0O3—C15—C16—S278.5 (2)
C2A—C1A—C6A—C5A0.0C13—C15—C16—S240.4 (3)
C7—C1A—C6A—C5A179.6 (5)C17—S2—C16—C1517.7 (2)
C2A—C1A—C7—C1091.3 (6)C12—C13—C17—C1842.0 (3)
C6A—C1A—C7—C1089.1 (6)C14—C13—C17—C1881.6 (3)
C2A—C1A—C7—S130.8 (6)C15—C13—C17—C18160.2 (2)
C6A—C1A—C7—S1148.8 (6)C12—C13—C17—S285.0 (2)
C2—C1—C7—C10112.3 (8)C14—C13—C17—S2151.45 (16)
C6—C1—C7—C1065.5 (9)C15—C13—C17—S233.2 (2)
C2—C1—C7—S110.0 (9)C16—S2—C17—C18139.0 (2)
C6—C1—C7—S1172.2 (7)C16—S2—C17—C139.6 (2)
C8—S1—C7—C1A143.9 (3)C13—C17—C18—C1988.8 (3)
C8—S1—C7—C1143.4 (4)S2—C17—C18—C19147.2 (2)
C8—S1—C7—C1015.9 (2)C13—C17—C18—C2394.2 (3)
C7—S1—C8—C912.3 (2)S2—C17—C18—C2329.8 (3)
S1—C8—C9—O183.4 (2)C23—C18—C19—C200.7 (4)
S1—C8—C9—C1037.3 (3)C17—C18—C19—C20176.4 (3)
C1A—C7—C10—C1144.5 (5)C18—C19—C20—C210.4 (5)
C1—C7—C10—C1145.3 (6)C19—C20—C21—C220.6 (5)
S1—C7—C10—C1180.7 (2)C20—C21—C22—C230.3 (6)
C1A—C7—C10—C1480.5 (5)C21—C22—C23—C181.5 (5)
C1—C7—C10—C1479.6 (6)C19—C18—C23—C221.6 (5)
S1—C7—C10—C14154.29 (17)C17—C18—C23—C22175.4 (3)
C1A—C7—C10—C9163.8 (4)C11—N—C24—C25A69.8 (7)
C1—C7—C10—C9164.7 (6)C12—N—C24—C25A168.5 (7)
S1—C7—C10—C938.6 (2)C11—N—C24—C2567.9 (4)
O1—C9—C10—C11171.5 (2)C12—N—C24—C25170.4 (3)
C8—C9—C10—C1170.8 (3)N—C24—C25—C2666.9 (5)
O1—C9—C10—C1450.2 (3)N—C24—C25—C30112.9 (5)
C8—C9—C10—C14167.9 (2)C30—C25—C26—C270.0
O1—C9—C10—C768.2 (3)C24—C25—C26—C27179.8 (5)
C8—C9—C10—C749.5 (3)C25—C26—C27—C280.0
C12—N—C11—C1068.0 (3)C26—C27—C28—C290.0
C24—N—C11—C10168.2 (2)C27—C28—C29—C300.0
C14—C10—C11—N48.1 (3)C28—C29—C30—C250.0
C7—C10—C11—N173.3 (2)C26—C25—C30—C290.0
C9—C10—C11—N71.1 (3)C24—C25—C30—C29179.8 (5)
C11—N—C12—C1371.5 (3)N—C24—C25A—C26A48.5 (9)
C24—N—C12—C13165.1 (2)N—C24—C25A—C30A135.6 (10)
N—C12—C13—C1455.1 (3)C30A—C25A—C26A—C27A0.0
N—C12—C13—C1565.1 (3)C24—C25A—C26A—C27A176.1 (11)
N—C12—C13—C17178.9 (2)C25A—C26A—C27A—C28A0.0
C11—C10—C14—O2146.7 (2)C26A—C27A—C28A—C29A0.0
C7—C10—C14—O221.3 (3)C27A—C28A—C29A—C30A0.0
C9—C10—C14—O292.3 (3)C28A—C29A—C30A—C25A0.0
C11—C10—C14—C1335.2 (3)C26A—C25A—C30A—C29A0.0
C7—C10—C14—C13160.5 (2)C24—C25A—C30A—C29A175.7 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.822.313.058 (3)152
O3—H3···O3i0.822.052.851 (3)167
Symmetry code: (i) y1, x+1, z+1.
 

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