13-Benzyl-4,11-dihy­droxy-1,8-diphen­yl-2,9-di­thia-13-aza­dispiro­[4.1.4.3]tetra­decan-6-one

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.

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

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

Crystal data

C30H31NO3S2	Melting point: 476.15 K
Mr = 517.68	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P421c	Cell parameters from 6903 reflections
a = 25.3750 (4) Å	θ = 1.1–28.3°
c = 8.6456 (2) Å	µ = 0.22 mm^−1
V = 5566.8 (2) Å^3	T = 293 K
Z = 8	Block, colourless
F(000) = 2192	0.28 × 0.24 × 0.20 mm
Dx = 1.235 Mg m^−3

Data collection

Bruker SMART APEXII area-detector diffractometer	5681 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.033
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 28.3°, θmin = 1.8°
Tmin = 0.685, Tmax = 0.742	h = −33→23
30401 measured reflections	k = −33→27
6899 independent reflections	l = −11→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0659P)^2 + 0.1922P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
6899 reflections	Δρmax = 0.27 e Å^−3
389 parameters	Δρmin = −0.15 e Å^−3
408 restraints	Absolute structure: Flack x determined using 2151 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (2)

Special details

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 U_iso(H) = 1.5U_eq(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 1.2U_eq(C) for H atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.19875 (3)	0.80219 (4)	0.82727 (10)	0.0581 (2)
S2	0.07519 (3)	0.97740 (3)	0.14696 (9)	0.04708 (19)
N	0.13618 (9)	0.81533 (8)	0.3251 (2)	0.0365 (5)
O1	0.10182 (9)	0.88166 (9)	0.7697 (2)	0.0528 (5)
H1	0.083927	0.903237	0.722551	0.079*
O2	0.17096 (8)	0.94891 (7)	0.5606 (2)	0.0440 (5)
O3	0.05248 (7)	0.94022 (8)	0.4969 (2)	0.0414 (4)
H3	0.020531	0.939159	0.510786	0.062*
C1	0.2681 (4)	0.8548 (5)	0.6236 (10)	0.043 (3)	0.44 (2)
C2	0.3011 (6)	0.8117 (5)	0.6461 (15)	0.051 (2)	0.44 (2)
H2A	0.289787	0.783422	0.705944	0.061*	0.44 (2)
C3	0.3509 (6)	0.8109 (5)	0.5791 (16)	0.065 (2)	0.44 (2)
H3A	0.372892	0.782049	0.594152	0.078*	0.44 (2)
C4	0.3677 (4)	0.8532 (5)	0.4897 (13)	0.074 (2)	0.44 (2)
H4A	0.401038	0.852616	0.444862	0.089*	0.44 (2)
C5	0.3348 (5)	0.8963 (5)	0.4672 (18)	0.067 (2)	0.44 (2)
H5A	0.346080	0.924556	0.407363	0.081*	0.44 (2)
C6	0.2850 (4)	0.8971 (5)	0.5342 (17)	0.057 (2)	0.44 (2)
H6A	0.262974	0.925931	0.519155	0.068*	0.44 (2)
C1A	0.2679 (3)	0.8540 (4)	0.6274 (8)	0.0401 (19)	0.56 (2)
C2A	0.2951 (4)	0.8070 (3)	0.6069 (13)	0.0478 (18)	0.56 (2)
H2AA	0.279047	0.775147	0.631921	0.057*	0.56 (2)
C3A	0.3462 (4)	0.8075 (3)	0.5489 (12)	0.066 (2)	0.56 (2)
H3AA	0.364329	0.776020	0.535225	0.079*	0.56 (2)
C4A	0.3701 (3)	0.8551 (4)	0.5115 (11)	0.079 (2)	0.56 (2)
H4AA	0.404302	0.855444	0.472747	0.094*	0.56 (2)
C5A	0.3430 (4)	0.9022 (4)	0.5320 (17)	0.072 (2)	0.56 (2)
H5AA	0.358993	0.933996	0.506964	0.087*	0.56 (2)
C6A	0.2919 (3)	0.9016 (3)	0.5899 (14)	0.0524 (18)	0.56 (2)
H6AA	0.273711	0.933124	0.603660	0.063*	0.56 (2)
C7	0.21172 (10)	0.85613 (11)	0.6917 (3)	0.0370 (6)
H7	0.208163	0.889184	0.749387	0.044*
C8	0.13063 (12)	0.79323 (13)	0.7676 (4)	0.0495 (7)
H8A	0.126873	0.760935	0.708600	0.059*
H8B	0.107757	0.791298	0.857322	0.059*
C9	0.11644 (10)	0.84041 (10)	0.6689 (3)	0.0381 (6)
H9	0.086970	0.831599	0.600358	0.046*
C10	0.16622 (10)	0.85436 (10)	0.5712 (3)	0.0319 (5)
C11	0.17586 (11)	0.81241 (10)	0.4471 (3)	0.0380 (6)
H11A	0.210565	0.817450	0.402454	0.046*
H11B	0.174908	0.777734	0.494223	0.046*
C12	0.14383 (11)	0.86442 (10)	0.2399 (3)	0.0381 (6)
H12A	0.123068	0.863910	0.145687	0.046*
H12B	0.180634	0.868270	0.211807	0.046*
C13	0.12668 (9)	0.91073 (9)	0.3422 (3)	0.0314 (5)
C14	0.15673 (9)	0.90880 (10)	0.4977 (3)	0.0315 (5)
C15	0.06627 (10)	0.90622 (10)	0.3714 (3)	0.0352 (5)
H15	0.057208	0.869749	0.397543	0.042*
C16	0.03912 (11)	0.92192 (12)	0.2229 (4)	0.0457 (7)
H16A	0.002780	0.931643	0.242898	0.055*
H16B	0.039538	0.892939	0.149758	0.055*
C17	0.13408 (10)	0.96560 (10)	0.2640 (3)	0.0350 (5)
H17	0.133754	0.991842	0.347127	0.042*
C18	0.18491 (10)	0.97408 (9)	0.1735 (3)	0.0374 (5)
C19	0.22921 (12)	0.99325 (12)	0.2497 (4)	0.0505 (7)
H19	0.227904	0.998813	0.355936	0.061*
C20	0.27490 (14)	1.00411 (13)	0.1705 (5)	0.0645 (9)
H20	0.304160	1.016710	0.223658	0.077*
C21	0.27770 (16)	0.99650 (13)	0.0129 (5)	0.0681 (10)
H21	0.308518	1.004157	−0.040764	0.082*
C22	0.23375 (16)	0.97718 (14)	−0.0645 (4)	0.0664 (10)
H22	0.235172	0.972066	−0.170956	0.080*
C23	0.18816 (13)	0.96554 (12)	0.0146 (3)	0.0499 (7)
H23	0.159320	0.951888	−0.038361	0.060*
C24	0.13841 (13)	0.76884 (11)	0.2234 (3)	0.0473 (7)
H24A	0.174111	0.764142	0.185664	0.057*
H24B	0.115547	0.774237	0.134857	0.057*
C25	0.1210 (3)	0.71931 (18)	0.3115 (8)	0.0449 (15)	0.672 (16)
C26	0.0695 (2)	0.7125 (3)	0.3626 (11)	0.0587 (17)	0.672 (16)
H26A	0.044391	0.738401	0.343379	0.070*	0.672 (16)
C27	0.0556 (2)	0.6671 (3)	0.4425 (10)	0.086 (2)	0.672 (16)
H27A	0.021107	0.662541	0.476661	0.103*	0.672 (16)
C28	0.0931 (4)	0.6284 (2)	0.4712 (9)	0.097 (2)	0.672 (16)
H28A	0.083765	0.597997	0.524630	0.116*	0.672 (16)
C29	0.1446 (3)	0.6352 (2)	0.4201 (10)	0.089 (2)	0.672 (16)
H29A	0.169708	0.609312	0.439317	0.106*	0.672 (16)
C30	0.1585 (3)	0.6806 (2)	0.3402 (9)	0.0669 (17)	0.672 (16)
H30A	0.192993	0.685172	0.306033	0.080*	0.672 (16)
C25A	0.1208 (6)	0.7211 (4)	0.2988 (18)	0.048 (3)	0.328 (16)
C26A	0.0731 (6)	0.7254 (5)	0.377 (2)	0.054 (3)	0.328 (16)
H26B	0.056243	0.757823	0.383767	0.065*	0.328 (16)
C27A	0.0508 (5)	0.6812 (6)	0.446 (2)	0.080 (3)	0.328 (16)
H27B	0.018955	0.684108	0.498750	0.096*	0.328 (16)
C28A	0.0761 (6)	0.6327 (5)	0.4366 (19)	0.089 (3)	0.328 (16)
H28B	0.061129	0.603172	0.482718	0.106*	0.328 (16)
C29A	0.1237 (7)	0.6284 (4)	0.358 (2)	0.086 (3)	0.328 (16)
H29B	0.140592	0.595950	0.351704	0.103*	0.328 (16)
C30A	0.1460 (5)	0.6726 (5)	0.2892 (19)	0.069 (3)	0.328 (16)
H30B	0.177882	0.669665	0.236720	0.083*	0.328 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0511 (4)	0.0731 (5)	0.0502 (4)	−0.0028 (4)	−0.0115 (4)	0.0292 (4)
S2	0.0453 (4)	0.0521 (4)	0.0438 (4)	0.0018 (3)	−0.0063 (3)	0.0186 (3)
N	0.0486 (12)	0.0305 (10)	0.0305 (11)	−0.0012 (9)	−0.0034 (10)	−0.0029 (9)
O1	0.0582 (13)	0.0577 (13)	0.0424 (11)	0.0094 (10)	0.0105 (10)	−0.0008 (10)
O2	0.0581 (12)	0.0362 (10)	0.0377 (10)	−0.0013 (8)	−0.0104 (9)	−0.0039 (8)
O3	0.0374 (10)	0.0483 (11)	0.0386 (10)	0.0014 (8)	0.0034 (8)	0.0008 (9)
C1	0.039 (5)	0.044 (5)	0.046 (5)	0.005 (4)	−0.009 (4)	0.001 (4)
C2	0.046 (4)	0.045 (4)	0.060 (5)	−0.002 (3)	−0.010 (4)	0.003 (4)
C3	0.047 (4)	0.065 (4)	0.084 (5)	0.011 (4)	0.000 (4)	−0.004 (4)
C4	0.051 (4)	0.080 (5)	0.091 (5)	0.006 (4)	0.016 (4)	0.000 (4)
C5	0.054 (4)	0.072 (4)	0.076 (6)	−0.002 (3)	0.009 (5)	0.009 (5)
C6	0.049 (4)	0.053 (4)	0.068 (6)	0.005 (3)	0.006 (4)	0.013 (4)
C1A	0.037 (4)	0.043 (4)	0.040 (4)	0.002 (3)	−0.006 (3)	0.002 (3)
C2A	0.043 (3)	0.049 (3)	0.051 (4)	0.002 (2)	−0.013 (3)	−0.008 (3)
C3A	0.050 (3)	0.065 (4)	0.081 (4)	0.016 (3)	−0.005 (3)	−0.012 (3)
C4A	0.049 (4)	0.084 (4)	0.102 (5)	0.007 (3)	0.019 (4)	0.004 (4)
C5A	0.052 (4)	0.072 (4)	0.092 (6)	−0.001 (3)	0.014 (4)	0.016 (4)
C6A	0.047 (3)	0.048 (3)	0.062 (5)	0.009 (3)	0.003 (3)	0.010 (3)
C7	0.0398 (13)	0.0405 (13)	0.0308 (13)	0.0000 (11)	−0.0042 (10)	0.0058 (11)
C8	0.0467 (16)	0.0555 (17)	0.0464 (16)	−0.0029 (13)	−0.0034 (13)	0.0175 (14)
C9	0.0404 (13)	0.0428 (13)	0.0310 (13)	−0.0013 (11)	0.0000 (11)	0.0049 (12)
C10	0.0346 (12)	0.0328 (12)	0.0282 (12)	−0.0003 (9)	−0.0023 (10)	0.0027 (10)
C11	0.0426 (14)	0.0332 (13)	0.0382 (13)	0.0037 (10)	−0.0015 (11)	0.0006 (11)
C12	0.0484 (15)	0.0357 (13)	0.0302 (12)	0.0013 (11)	0.0003 (12)	−0.0004 (11)
C13	0.0350 (12)	0.0318 (11)	0.0272 (11)	−0.0003 (9)	−0.0006 (10)	0.0029 (10)
C14	0.0319 (12)	0.0372 (13)	0.0254 (11)	0.0021 (10)	0.0012 (10)	0.0013 (10)
C15	0.0355 (13)	0.0378 (13)	0.0324 (13)	−0.0028 (10)	−0.0025 (11)	0.0040 (11)
C16	0.0442 (15)	0.0496 (16)	0.0432 (16)	−0.0022 (12)	−0.0107 (12)	0.0070 (13)
C17	0.0396 (13)	0.0340 (12)	0.0313 (12)	0.0015 (10)	−0.0037 (11)	0.0042 (10)
C18	0.0454 (14)	0.0285 (12)	0.0383 (13)	0.0009 (10)	0.0030 (11)	0.0043 (11)
C19	0.0462 (16)	0.0539 (17)	0.0514 (17)	−0.0058 (13)	0.0004 (14)	0.0103 (15)
C20	0.0486 (18)	0.061 (2)	0.084 (3)	−0.0088 (15)	−0.0008 (19)	0.0099 (19)
C21	0.066 (2)	0.0541 (19)	0.085 (3)	−0.0054 (16)	0.038 (2)	0.0046 (19)
C22	0.089 (3)	0.0534 (19)	0.057 (2)	−0.0153 (18)	0.031 (2)	−0.0065 (17)
C23	0.0624 (18)	0.0438 (15)	0.0436 (16)	−0.0117 (13)	0.0110 (14)	−0.0027 (13)
C24	0.0670 (19)	0.0379 (14)	0.0370 (15)	−0.0026 (13)	0.0065 (14)	−0.0078 (12)
C25	0.053 (3)	0.034 (3)	0.047 (3)	−0.006 (2)	0.001 (3)	−0.007 (2)
C26	0.054 (3)	0.042 (3)	0.081 (4)	−0.009 (3)	0.001 (3)	0.001 (3)
C27	0.089 (4)	0.060 (5)	0.110 (4)	−0.021 (3)	0.024 (4)	0.008 (4)
C28	0.127 (5)	0.055 (3)	0.109 (5)	−0.014 (4)	0.004 (4)	0.023 (3)
C29	0.109 (5)	0.045 (3)	0.112 (5)	0.014 (3)	−0.017 (4)	0.005 (3)
C30	0.071 (3)	0.041 (3)	0.089 (4)	0.004 (2)	−0.003 (3)	−0.009 (3)
C25A	0.055 (5)	0.033 (5)	0.056 (5)	0.003 (5)	−0.005 (5)	−0.009 (5)
C26A	0.061 (5)	0.033 (5)	0.070 (5)	−0.018 (4)	0.004 (4)	−0.008 (5)
C27A	0.089 (5)	0.046 (6)	0.106 (6)	−0.014 (4)	0.016 (5)	0.005 (5)
C28A	0.105 (6)	0.050 (5)	0.111 (6)	−0.012 (5)	0.007 (5)	0.024 (5)
C29A	0.102 (6)	0.038 (4)	0.117 (7)	0.006 (5)	−0.007 (6)	0.008 (5)
C30A	0.073 (5)	0.036 (4)	0.098 (6)	0.002 (4)	0.002 (5)	−0.011 (5)

Geometric parameters (Å, º)

S1—C8	1.818 (3)	C12—H12A	0.9700
S1—C7	1.832 (3)	C12—H12B	0.9700
S2—C16	1.803 (3)	C13—C14	1.546 (3)
S2—C17	1.829 (3)	C13—C15	1.558 (3)
N—C11	1.460 (3)	C13—C17	1.559 (3)
N—C12	1.460 (3)	C15—C16	1.511 (4)
N—C24	1.473 (3)	C15—H15	0.9800
O1—C9	1.412 (3)	C16—H16A	0.9700
O1—H1	0.8200	C16—H16B	0.9700
O2—C14	1.209 (3)	C17—C18	1.524 (4)
O3—C15	1.430 (3)	C17—H17	0.9800
O3—H3	0.8200	C18—C19	1.390 (4)
C1—C2	1.3900	C18—C23	1.394 (4)
C1—C6	1.3900	C19—C20	1.374 (5)
C1—C7	1.548 (10)	C19—H19	0.9300
C2—C3	1.3900	C20—C21	1.377 (6)
C2—H2A	0.9300	C20—H20	0.9300
C3—C4	1.3900	C21—C22	1.390 (6)
C3—H3A	0.9300	C21—H21	0.9300
C4—C5	1.3900	C22—C23	1.376 (5)
C4—H4A	0.9300	C22—H22	0.9300
C5—C6	1.3900	C23—H23	0.9300
C5—H5A	0.9300	C24—C25A	1.448 (10)
C6—H6A	0.9300	C24—C25	1.535 (6)
C1A—C2A	1.3900	C24—H24A	0.9700
C1A—C6A	1.3900	C24—H24B	0.9700
C1A—C7	1.532 (8)	C25—C26	1.3900
C2A—C3A	1.3900	C25—C30	1.3900
C2A—H2AA	0.9300	C26—C27	1.3900
C3A—C4A	1.3900	C26—H26A	0.9300
C3A—H3AA	0.9300	C27—C28	1.3900
C4A—C5A	1.3900	C27—H27A	0.9300
C4A—H4AA	0.9300	C28—C29	1.3900
C5A—C6A	1.3900	C28—H28A	0.9300
C5A—H5AA	0.9300	C29—C30	1.3900
C6A—H6AA	0.9300	C29—H29A	0.9300
C7—C10	1.556 (3)	C30—H30A	0.9300
C7—H7	0.9800	C25A—C26A	1.3900
C8—C9	1.514 (4)	C25A—C30A	1.3900
C8—H8A	0.9700	C26A—C27A	1.3900
C8—H8B	0.9700	C26A—H26B	0.9300
C9—C10	1.560 (4)	C27A—C28A	1.3900
C9—H9	0.9800	C27A—H27B	0.9300
C10—C11	1.531 (3)	C28A—C29A	1.3900
C10—C14	1.540 (3)	C28A—H28B	0.9300
C11—H11A	0.9700	C29A—C30A	1.3900
C11—H11B	0.9700	C29A—H29B	0.9300
C12—C13	1.534 (4)	C30A—H30B	0.9300
C8—S1—C7	94.74 (12)	C14—C13—C17	110.24 (19)
C16—S2—C17	94.91 (12)	C15—C13—C17	104.74 (19)
C11—N—C12	108.4 (2)	O2—C14—C10	121.5 (2)
C11—N—C24	111.4 (2)	O2—C14—C13	120.8 (2)
C12—N—C24	112.1 (2)	C10—C14—C13	117.7 (2)
C9—O1—H1	109.5	O3—C15—C16	112.0 (2)
C15—O3—H3	109.5	O3—C15—C13	108.7 (2)
C2—C1—C6	120.0	C16—C15—C13	106.9 (2)
C2—C1—C7	121.3 (8)	O3—C15—H15	109.7
C6—C1—C7	118.6 (8)	C16—C15—H15	109.7
C3—C2—C1	120.0	C13—C15—H15	109.7
C3—C2—H2A	120.0	C15—C16—S2	106.49 (19)
C1—C2—H2A	120.0	C15—C16—H16A	110.4
C4—C3—C2	120.0	S2—C16—H16A	110.4
C4—C3—H3A	120.0	C15—C16—H16B	110.4
C2—C3—H3A	120.0	S2—C16—H16B	110.4
C3—C4—C5	120.0	H16A—C16—H16B	108.6
C3—C4—H4A	120.0	C18—C17—C13	116.8 (2)
C5—C4—H4A	120.0	C18—C17—S2	112.63 (18)
C6—C5—C4	120.0	C13—C17—S2	106.71 (16)
C6—C5—H5A	120.0	C18—C17—H17	106.7
C4—C5—H5A	120.0	C13—C17—H17	106.7
C5—C6—C1	120.0	S2—C17—H17	106.7
C5—C6—H6A	120.0	C19—C18—C23	118.3 (3)
C1—C6—H6A	120.0	C19—C18—C17	119.4 (2)
C2A—C1A—C6A	120.0	C23—C18—C17	122.3 (3)
C2A—C1A—C7	122.5 (6)	C20—C19—C18	121.1 (3)
C6A—C1A—C7	117.5 (6)	C20—C19—H19	119.5
C1A—C2A—C3A	120.0	C18—C19—H19	119.5
C1A—C2A—H2AA	120.0	C19—C20—C21	120.5 (3)
C3A—C2A—H2AA	120.0	C19—C20—H20	119.7
C4A—C3A—C2A	120.0	C21—C20—H20	119.7
C4A—C3A—H3AA	120.0	C20—C21—C22	119.0 (3)
C2A—C3A—H3AA	120.0	C20—C21—H21	120.5
C3A—C4A—C5A	120.0	C22—C21—H21	120.5
C3A—C4A—H4AA	120.0	C23—C22—C21	120.7 (3)
C5A—C4A—H4AA	120.0	C23—C22—H22	119.6
C4A—C5A—C6A	120.0	C21—C22—H22	119.6
C4A—C5A—H5AA	120.0	C22—C23—C18	120.4 (3)
C6A—C5A—H5AA	120.0	C22—C23—H23	119.8
C5A—C6A—C1A	120.0	C18—C23—H23	119.8
C5A—C6A—H6AA	120.0	C25A—C24—N	112.9 (6)
C1A—C6A—H6AA	120.0	N—C24—C25	110.4 (3)
C1A—C7—C10	116.6 (3)	N—C24—H24A	109.6
C1—C7—C10	115.5 (4)	C25—C24—H24A	109.6
C1A—C7—S1	111.9 (4)	N—C24—H24B	109.6
C1—C7—S1	113.1 (5)	C25—C24—H24B	109.6
C10—C7—S1	105.87 (16)	H24A—C24—H24B	108.1
C1—C7—H7	107.3	C26—C25—C30	120.0
C10—C7—H7	107.3	C26—C25—C24	122.0 (4)
S1—C7—H7	107.3	C30—C25—C24	118.0 (4)
C9—C8—S1	106.7 (2)	C27—C26—C25	120.0
C9—C8—H8A	110.4	C27—C26—H26A	120.0
S1—C8—H8A	110.4	C25—C26—H26A	120.0
C9—C8—H8B	110.4	C26—C27—C28	120.0
S1—C8—H8B	110.4	C26—C27—H27A	120.0
H8A—C8—H8B	108.6	C28—C27—H27A	120.0
O1—C9—C8	107.5 (2)	C27—C28—C29	120.0
O1—C9—C10	112.3 (2)	C27—C28—H28A	120.0
C8—C9—C10	107.0 (2)	C29—C28—H28A	120.0
O1—C9—H9	110.0	C30—C29—C28	120.0
C8—C9—H9	110.0	C30—C29—H29A	120.0
C10—C9—H9	110.0	C28—C29—H29A	120.0
C11—C10—C14	111.0 (2)	C29—C30—C25	120.0
C11—C10—C7	111.8 (2)	C29—C30—H30A	120.0
C14—C10—C7	111.51 (19)	C25—C30—H30A	120.0
C11—C10—C9	110.5 (2)	C26A—C25A—C30A	120.0
C14—C10—C9	107.49 (19)	C26A—C25A—C24	115.0 (10)
C7—C10—C9	104.2 (2)	C30A—C25A—C24	124.9 (10)
N—C11—C10	111.2 (2)	C25A—C26A—C27A	120.0
N—C11—H11A	109.4	C25A—C26A—H26B	120.0
C10—C11—H11A	109.4	C27A—C26A—H26B	120.0
N—C11—H11B	109.4	C26A—C27A—C28A	120.0
C10—C11—H11B	109.4	C26A—C27A—H27B	120.0
H11A—C11—H11B	108.0	C28A—C27A—H27B	120.0
N—C12—C13	109.0 (2)	C29A—C28A—C27A	120.0
N—C12—H12A	109.9	C29A—C28A—H28B	120.0
C13—C12—H12A	109.9	C27A—C28A—H28B	120.0
N—C12—H12B	109.9	C28A—C29A—C30A	120.0
C13—C12—H12B	109.9	C28A—C29A—H29B	120.0
H12A—C12—H12B	108.3	C30A—C29A—H29B	120.0
C12—C13—C14	109.70 (19)	C29A—C30A—C25A	120.0
C12—C13—C15	108.5 (2)	C29A—C30A—H30B	120.0
C14—C13—C15	109.98 (19)	C25A—C30A—H30B	120.0
C12—C13—C17	113.6 (2)
C6—C1—C2—C3	0.0	C9—C10—C14—C13	−85.9 (2)
C7—C1—C2—C3	177.8 (7)	C12—C13—C14—O2	143.1 (2)
C1—C2—C3—C4	0.0	C15—C13—C14—O2	−97.7 (3)
C2—C3—C4—C5	0.0	C17—C13—C14—O2	17.3 (3)
C3—C4—C5—C6	0.0	C12—C13—C14—C10	−38.7 (3)
C4—C5—C6—C1	0.0	C15—C13—C14—C10	80.5 (2)
C2—C1—C6—C5	0.0	C17—C13—C14—C10	−164.5 (2)
C7—C1—C6—C5	−177.8 (7)	C12—C13—C15—O3	165.0 (2)
C6A—C1A—C2A—C3A	0.0	C14—C13—C15—O3	45.1 (3)
C7—C1A—C2A—C3A	−179.6 (6)	C17—C13—C15—O3	−73.4 (2)
C1A—C2A—C3A—C4A	0.0	C12—C13—C15—C16	−74.0 (3)
C2A—C3A—C4A—C5A	0.0	C14—C13—C15—C16	166.1 (2)
C3A—C4A—C5A—C6A	0.0	C17—C13—C15—C16	47.6 (3)
C4A—C5A—C6A—C1A	0.0	O3—C15—C16—S2	78.5 (2)
C2A—C1A—C6A—C5A	0.0	C13—C15—C16—S2	−40.4 (3)
C7—C1A—C6A—C5A	179.6 (5)	C17—S2—C16—C15	17.7 (2)
C2A—C1A—C7—C10	−91.3 (6)	C12—C13—C17—C18	−42.0 (3)
C6A—C1A—C7—C10	89.1 (6)	C14—C13—C17—C18	81.6 (3)
C2A—C1A—C7—S1	30.8 (6)	C15—C13—C17—C18	−160.2 (2)
C6A—C1A—C7—S1	−148.8 (6)	C12—C13—C17—S2	85.0 (2)
C2—C1—C7—C10	−112.3 (8)	C14—C13—C17—S2	−151.45 (16)
C6—C1—C7—C10	65.5 (9)	C15—C13—C17—S2	−33.2 (2)
C2—C1—C7—S1	10.0 (9)	C16—S2—C17—C18	139.0 (2)
C6—C1—C7—S1	−172.2 (7)	C16—S2—C17—C13	9.6 (2)
C8—S1—C7—C1A	−143.9 (3)	C13—C17—C18—C19	−88.8 (3)
C8—S1—C7—C1	−143.4 (4)	S2—C17—C18—C19	147.2 (2)
C8—S1—C7—C10	−15.9 (2)	C13—C17—C18—C23	94.2 (3)
C7—S1—C8—C9	−12.3 (2)	S2—C17—C18—C23	−29.8 (3)
S1—C8—C9—O1	−83.4 (2)	C23—C18—C19—C20	0.7 (4)
S1—C8—C9—C10	37.3 (3)	C17—C18—C19—C20	−176.4 (3)
C1A—C7—C10—C11	44.5 (5)	C18—C19—C20—C21	0.4 (5)
C1—C7—C10—C11	45.3 (6)	C19—C20—C21—C22	−0.6 (5)
S1—C7—C10—C11	−80.7 (2)	C20—C21—C22—C23	−0.3 (6)
C1A—C7—C10—C14	−80.5 (5)	C21—C22—C23—C18	1.5 (5)
C1—C7—C10—C14	−79.6 (6)	C19—C18—C23—C22	−1.6 (5)
S1—C7—C10—C14	154.29 (17)	C17—C18—C23—C22	175.4 (3)
C1A—C7—C10—C9	163.8 (4)	C11—N—C24—C25A	69.8 (7)
C1—C7—C10—C9	164.7 (6)	C12—N—C24—C25A	−168.5 (7)
S1—C7—C10—C9	38.6 (2)	C11—N—C24—C25	67.9 (4)
O1—C9—C10—C11	−171.5 (2)	C12—N—C24—C25	−170.4 (3)
C8—C9—C10—C11	70.8 (3)	N—C24—C25—C26	66.9 (5)
O1—C9—C10—C14	−50.2 (3)	N—C24—C25—C30	−112.9 (5)
C8—C9—C10—C14	−167.9 (2)	C30—C25—C26—C27	0.0
O1—C9—C10—C7	68.2 (3)	C24—C25—C26—C27	−179.8 (5)
C8—C9—C10—C7	−49.5 (3)	C25—C26—C27—C28	0.0
C12—N—C11—C10	68.0 (3)	C26—C27—C28—C29	0.0
C24—N—C11—C10	−168.2 (2)	C27—C28—C29—C30	0.0
C14—C10—C11—N	−48.1 (3)	C28—C29—C30—C25	0.0
C7—C10—C11—N	−173.3 (2)	C26—C25—C30—C29	0.0
C9—C10—C11—N	71.1 (3)	C24—C25—C30—C29	179.8 (5)
C11—N—C12—C13	−71.5 (3)	N—C24—C25A—C26A	48.5 (9)
C24—N—C12—C13	165.1 (2)	N—C24—C25A—C30A	−135.6 (10)
N—C12—C13—C14	55.1 (3)	C30A—C25A—C26A—C27A	0.0
N—C12—C13—C15	−65.1 (3)	C24—C25A—C26A—C27A	176.1 (11)
N—C12—C13—C17	178.9 (2)	C25A—C26A—C27A—C28A	0.0
C11—C10—C14—O2	−146.7 (2)	C26A—C27A—C28A—C29A	0.0
C7—C10—C14—O2	−21.3 (3)	C27A—C28A—C29A—C30A	0.0
C9—C10—C14—O2	92.3 (3)	C28A—C29A—C30A—C25A	0.0
C11—C10—C14—C13	35.2 (3)	C26A—C25A—C30A—C29A	0.0
C7—C10—C14—C13	160.5 (2)	C24—C25A—C30A—C29A	−175.7 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.82	2.31	3.058 (3)	152
O3—H3···O3^i	0.82	2.05	2.851 (3)	167

Symmetry code: (i) y−1, −x+1, −z+1.