Crystal structures of two 2,9-di­thia-13-aza­dispiro­[4.1.4⁷.3⁵]tetra­decan-6-ones

The title compounds, (I) and (II), differ only in the substituent on the N atom of the central piperidine ring; methyl in (I) and benzyl in (II). In each mol­ecule, the 4,11-dihy­droxy groups are involved in intra­molecular O—H...O hydrogen bonds. In the crystal of (I), mol­ecules are linked via O—H...N hydrogen bonds, forming chains along the b-axis direction. In the crystal of (II), mol­ecules are linked via O—H...O hydrogen bonds, forming inversion dimers with an (8) ring motif.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.052
• wR factor = 0.141
• Data-to-parameter ratio = 20.0

Structure: II

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.136
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT220_ALERT_2_C Large Non-Solvent  C     Ueq(max)/Ueq(min) Range        4.1 Ratio
PLAT222_ALERT_3_C Large Non-Solvent  H     Uiso(max)/Uiso(min) ...        4.6 Ratio
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....         S2 Check
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....        C23 Check
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....        C19 Check
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....        C22 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.496 Check

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT793_ALERT_4_G The Model has Chirality at C7      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C9      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C10     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C14     (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C16     (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C18     (Centro SPGR)          R Verify
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         18 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  14 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   9 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT220_ALERT_2_C Large Non-Solvent  C     Ueq(max)/Ueq(min) Range        3.2 Ratio
PLAT222_ALERT_3_C Large Non-Solvent  H     Uiso(max)/Uiso(min) ...        6.7 Ratio
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....         S1 Check
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....        C16 Check
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -2.589 Report
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          8 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT793_ALERT_4_G The Model has Chirality at C7      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C9      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C10     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C13     (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C15     (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C17     (Centro SPGR)          R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         41 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  14 ALERT level G = General information/check it is not something unexpected

   3 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
   4 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

Computing details

For both compounds, 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: SHELXL97 (Sheldrick, 2008). Molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008) for (I); ORTEP-3 for Windows (Farrugia, 2012) for (II). For both compounds, software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

(I) 4,11-Dihydroxy-13-methyl-1,8-di-p-tolyl-2,9-dithia-13-azadispiro[4.1.4⁷.3⁵]tetradecan-6-one

Crystal data

C26H31NO3S2	F(000) = 1000
Mr = 469.64	Dx = 1.325 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5871 reflections
a = 10.7160 (8) Å	θ = 1.6–28.4°
b = 8.5570 (5) Å	µ = 0.26 mm^−1
c = 25.6960 (3) Å	T = 293 K
β = 92.374 (5)°	Block, colourless
V = 2354.2 (2) Å^3	0.23 × 0.16 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEXII area-detector diffractometer	5871 independent reflections
Radiation source: fine-focus sealed tube	4793 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω and φ scans	θmax = 28.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→11
Tmin = 0.944, Tmax = 0.975	k = −11→10
21401 measured reflections	l = −34→33

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0662P)^2 + 1.3213P] where P = (Fo^2 + 2Fc^2)/3
5871 reflections	(Δ/σ)max = 0.003
294 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −0.73 e Å^−3

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. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	0.4048 (2)	0.3240 (4)	0.03800 (10)	0.0719 (8)
C2	0.3926 (2)	0.4410 (4)	0.07393 (10)	0.0664 (7)
H2	0.3493	0.5313	0.0642	0.080*
C3	0.44302 (18)	0.4284 (3)	0.12434 (9)	0.0505 (5)
H3	0.4324	0.5097	0.1478	0.061*
C4	0.50904 (16)	0.2962 (2)	0.14024 (7)	0.0398 (4)
C5	0.5191 (2)	0.1764 (3)	0.10455 (10)	0.0628 (7)
H5	0.5603	0.0847	0.1144	0.075*
C6	0.4687 (3)	0.1914 (4)	0.05435 (11)	0.0801 (9)
H6	0.4781	0.1099	0.0309	0.096*
C7	0.57099 (15)	0.2778 (2)	0.19388 (7)	0.0333 (3)
H7	0.5748	0.1657	0.2015	0.040*
C8	0.61777 (19)	0.4164 (3)	0.28561 (8)	0.0506 (5)
H8A	0.6268	0.5288	0.2886	0.061*
H8B	0.6088	0.3736	0.3202	0.061*
C9	0.73237 (16)	0.3465 (2)	0.26119 (6)	0.0350 (4)
H9	0.8056	0.4119	0.2695	0.042*
C10	0.70612 (14)	0.34308 (18)	0.20101 (6)	0.0271 (3)
C11	0.71732 (14)	0.50788 (19)	0.17824 (7)	0.0304 (3)
H11A	0.6813	0.5084	0.1430	0.036*
H11B	0.6696	0.5799	0.1987	0.036*
N1	0.84734 (12)	0.56261 (15)	0.17741 (5)	0.0292 (3)
C13	0.91738 (15)	0.46072 (19)	0.14329 (6)	0.0318 (3)
H13A	1.0008	0.5028	0.1401	0.038*
H13B	0.8767	0.4602	0.1089	0.038*
C14	0.92727 (14)	0.29212 (18)	0.16352 (6)	0.0281 (3)
O2	0.77004 (12)	0.09535 (14)	0.16831 (5)	0.0386 (3)
C16	1.01479 (16)	0.2846 (2)	0.21325 (7)	0.0353 (4)
H16	0.9936	0.3678	0.2375	0.042*
C17	1.14797 (17)	0.3050 (2)	0.19615 (9)	0.0494 (5)
H17A	1.2058	0.2529	0.2205	0.059*
H17B	1.1694	0.4150	0.1952	0.059*
C18	0.99011 (15)	0.1806 (2)	0.12465 (7)	0.0377 (4)
H18	0.9768	0.0736	0.1368	0.045*
C19	0.94465 (18)	0.1872 (2)	0.06847 (8)	0.0409 (4)
C20	0.8536 (2)	0.0833 (3)	0.05035 (9)	0.0619 (6)
H20	0.8218	0.0099	0.0730	0.074*
C21	0.8096 (3)	0.0873 (4)	−0.00077 (10)	0.0759 (8)
H21	0.7479	0.0171	−0.0119	0.091*
C22	0.8553 (3)	0.1937 (3)	−0.03593 (9)	0.0641 (7)
C23	0.9493 (4)	0.2889 (4)	−0.01808 (10)	0.0872 (10)
H23	0.9846	0.3581	−0.0412	0.105*
C24	0.9938 (3)	0.2863 (3)	0.03268 (10)	0.0762 (8)
H24	1.0585	0.3531	0.0431	0.091*
C25	0.8072 (4)	0.1958 (4)	−0.09210 (10)	0.0960 (11)
H25A	0.8141	0.2997	−0.1058	0.144*
H25B	0.7213	0.1638	−0.0940	0.144*
H25C	0.8558	0.1254	−0.1121	0.144*
C26	0.3467 (3)	0.3383 (6)	−0.01659 (11)	0.1097 (14)
H26A	0.2664	0.2885	−0.0180	0.165*
H26B	0.3999	0.2887	−0.0408	0.165*
H26C	0.3372	0.4468	−0.0255	0.165*
C12	0.79789 (14)	0.23038 (18)	0.17614 (6)	0.0269 (3)
O1	0.75164 (16)	0.19543 (18)	0.28197 (6)	0.0525 (4)
H1	0.8168	0.1593	0.2714	0.079*
C15	0.8473 (2)	0.7232 (2)	0.15654 (8)	0.0446 (4)
H15A	0.8097	0.7236	0.1220	0.067*
H15B	0.9317	0.7604	0.1555	0.067*
H15C	0.8006	0.7901	0.1785	0.067*
O3	0.99559 (13)	0.13534 (15)	0.23626 (6)	0.0469 (4)
H3A	1.0500	0.1195	0.2590	0.070*
S1	0.48173 (4)	0.36957 (7)	0.24461 (2)	0.04803 (15)
S2	1.15760 (5)	0.22095 (9)	0.13244 (3)	0.0704 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0418 (12)	0.126 (3)	0.0471 (12)	−0.0248 (14)	−0.0074 (10)	0.0022 (15)
C2	0.0447 (12)	0.0852 (18)	0.0676 (15)	−0.0093 (12)	−0.0171 (11)	0.0202 (14)
C3	0.0368 (10)	0.0577 (13)	0.0560 (12)	−0.0038 (9)	−0.0094 (8)	0.0011 (10)
C4	0.0253 (7)	0.0494 (11)	0.0442 (10)	−0.0069 (7)	−0.0038 (7)	−0.0061 (8)
C5	0.0459 (11)	0.0785 (17)	0.0628 (14)	0.0043 (11)	−0.0140 (10)	−0.0290 (13)
C6	0.0547 (14)	0.124 (3)	0.0605 (15)	−0.0036 (16)	−0.0079 (12)	−0.0399 (17)
C7	0.0265 (7)	0.0333 (8)	0.0399 (9)	−0.0033 (6)	0.0006 (6)	−0.0029 (7)
C8	0.0446 (10)	0.0681 (14)	0.0391 (10)	0.0032 (10)	0.0008 (8)	−0.0118 (10)
C9	0.0376 (8)	0.0361 (9)	0.0309 (8)	0.0005 (7)	−0.0045 (7)	0.0004 (7)
C10	0.0253 (7)	0.0252 (7)	0.0306 (7)	−0.0007 (6)	−0.0032 (6)	0.0002 (6)
C11	0.0275 (7)	0.0262 (8)	0.0369 (8)	0.0019 (6)	−0.0057 (6)	0.0019 (6)
N1	0.0308 (6)	0.0204 (6)	0.0356 (7)	−0.0021 (5)	−0.0067 (5)	0.0029 (5)
C13	0.0320 (8)	0.0275 (8)	0.0356 (8)	−0.0019 (6)	−0.0010 (6)	0.0045 (6)
C14	0.0254 (7)	0.0243 (7)	0.0343 (8)	−0.0003 (6)	−0.0039 (6)	−0.0002 (6)
O2	0.0362 (6)	0.0242 (6)	0.0553 (8)	−0.0033 (5)	−0.0002 (5)	−0.0032 (5)
C16	0.0311 (8)	0.0267 (8)	0.0468 (10)	0.0002 (6)	−0.0131 (7)	0.0022 (7)
C17	0.0302 (9)	0.0431 (11)	0.0735 (14)	−0.0027 (8)	−0.0142 (9)	−0.0014 (10)
C18	0.0286 (8)	0.0345 (9)	0.0501 (10)	−0.0001 (7)	0.0036 (7)	−0.0061 (8)
C19	0.0434 (9)	0.0361 (9)	0.0439 (10)	−0.0021 (8)	0.0114 (8)	−0.0066 (7)
C20	0.0665 (14)	0.0687 (15)	0.0501 (12)	−0.0223 (12)	−0.0034 (10)	0.0051 (11)
C21	0.0777 (18)	0.093 (2)	0.0565 (14)	−0.0207 (16)	−0.0076 (13)	−0.0030 (14)
C22	0.0916 (19)	0.0608 (15)	0.0403 (11)	0.0116 (14)	0.0070 (11)	−0.0041 (10)
C23	0.145 (3)	0.0724 (18)	0.0464 (13)	−0.034 (2)	0.0259 (16)	−0.0004 (13)
C24	0.102 (2)	0.0764 (18)	0.0517 (13)	−0.0419 (16)	0.0238 (14)	−0.0095 (12)
C25	0.152 (3)	0.091 (2)	0.0439 (14)	0.020 (2)	−0.0038 (17)	−0.0071 (14)
C26	0.079 (2)	0.196 (4)	0.0527 (16)	−0.046 (2)	−0.0196 (14)	0.019 (2)
C12	0.0272 (7)	0.0241 (7)	0.0289 (7)	0.0000 (6)	−0.0057 (6)	0.0019 (6)
O1	0.0690 (10)	0.0477 (8)	0.0404 (7)	0.0051 (7)	−0.0010 (7)	0.0140 (6)
C15	0.0531 (11)	0.0247 (8)	0.0552 (11)	−0.0025 (8)	−0.0083 (9)	0.0095 (8)
O3	0.0449 (7)	0.0321 (7)	0.0614 (9)	−0.0024 (6)	−0.0254 (6)	0.0127 (6)
S1	0.0324 (2)	0.0625 (3)	0.0495 (3)	−0.0011 (2)	0.00694 (19)	−0.0103 (2)
S2	0.0279 (2)	0.0881 (5)	0.0956 (5)	−0.0015 (3)	0.0089 (3)	−0.0326 (4)

Geometric parameters (Å, º)

C1—C2	1.372 (4)	C14—C16	1.555 (2)
C1—C6	1.382 (5)	O2—C12	1.2082 (19)
C1—C26	1.516 (4)	C16—O3	1.426 (2)
C2—C3	1.387 (3)	C16—C17	1.521 (3)
C2—H2	0.9300	C16—H16	0.9800
C3—C4	1.387 (3)	C17—S2	1.795 (2)
C3—H3	0.9300	C17—H17A	0.9700
C4—C5	1.383 (3)	C17—H17B	0.9700
C4—C7	1.513 (2)	C18—C19	1.505 (3)
C5—C6	1.384 (4)	C18—S2	1.8306 (18)
C5—H5	0.9300	C18—H18	0.9800
C6—H6	0.9300	C19—C24	1.372 (3)
C7—C10	1.556 (2)	C19—C20	1.386 (3)
C7—S1	1.8260 (18)	C20—C21	1.377 (3)
C7—H7	0.9800	C20—H20	0.9300
C8—C9	1.524 (3)	C21—C22	1.386 (4)
C8—S1	1.808 (2)	C21—H21	0.9300
C8—H8A	0.9700	C22—C23	1.360 (4)
C8—H8B	0.9700	C22—C25	1.512 (4)
C9—O1	1.411 (2)	C23—C24	1.370 (4)
C9—C10	1.560 (2)	C23—H23	0.9300
C9—H9	0.9800	C24—H24	0.9300
C10—C11	1.533 (2)	C25—H25A	0.9600
C10—C12	1.535 (2)	C25—H25B	0.9600
C11—N1	1.471 (2)	C25—H25C	0.9600
C11—H11A	0.9700	C26—H26A	0.9600
C11—H11B	0.9700	C26—H26B	0.9600
N1—C13	1.465 (2)	C26—H26C	0.9600
N1—C15	1.475 (2)	O1—H1	0.8200
C13—C14	1.536 (2)	C15—H15A	0.9600
C13—H13A	0.9700	C15—H15B	0.9600
C13—H13B	0.9700	C15—H15C	0.9600
C14—C12	1.531 (2)	O3—H3A	0.8200
C14—C18	1.555 (2)
C2—C1—C6	117.0 (2)	C18—C14—C16	103.88 (13)
C2—C1—C26	121.1 (3)	O3—C16—C17	112.07 (15)
C6—C1—C26	121.8 (3)	O3—C16—C14	106.59 (13)
C1—C2—C3	121.8 (3)	C17—C16—C14	107.41 (15)
C1—C2—H2	119.1	O3—C16—H16	110.2
C3—C2—H2	119.1	C17—C16—H16	110.2
C2—C3—C4	120.8 (2)	C14—C16—H16	110.2
C2—C3—H3	119.6	C16—C17—S2	107.92 (13)
C4—C3—H3	119.6	C16—C17—H17A	110.1
C5—C4—C3	117.6 (2)	S2—C17—H17A	110.1
C5—C4—C7	118.93 (19)	C16—C17—H17B	110.1
C3—C4—C7	123.51 (18)	S2—C17—H17B	110.1
C4—C5—C6	120.7 (3)	H17A—C17—H17B	108.4
C4—C5—H5	119.6	C19—C18—C14	117.47 (15)
C6—C5—H5	119.6	C19—C18—S2	112.00 (13)
C1—C6—C5	122.0 (3)	C14—C18—S2	105.22 (11)
C1—C6—H6	119.0	C19—C18—H18	107.2
C5—C6—H6	119.0	C14—C18—H18	107.2
C4—C7—C10	116.18 (14)	S2—C18—H18	107.2
C4—C7—S1	112.50 (12)	C24—C19—C20	117.1 (2)
C10—C7—S1	105.91 (11)	C24—C19—C18	123.24 (19)
C4—C7—H7	107.3	C20—C19—C18	119.57 (18)
C10—C7—H7	107.3	C21—C20—C19	120.8 (2)
S1—C7—H7	107.3	C21—C20—H20	119.6
C9—C8—S1	108.49 (13)	C19—C20—H20	119.6
C9—C8—H8A	110.0	C20—C21—C22	121.5 (3)
S1—C8—H8A	110.0	C20—C21—H21	119.3
C9—C8—H8B	110.0	C22—C21—H21	119.3
S1—C8—H8B	110.0	C23—C22—C21	116.7 (2)
H8A—C8—H8B	108.4	C23—C22—C25	122.2 (3)
O1—C9—C8	108.14 (16)	C21—C22—C25	121.0 (3)
O1—C9—C10	112.04 (14)	C22—C23—C24	122.4 (2)
C8—C9—C10	107.47 (14)	C22—C23—H23	118.8
O1—C9—H9	109.7	C24—C23—H23	118.8
C8—C9—H9	109.7	C23—C24—C19	121.3 (3)
C10—C9—H9	109.7	C23—C24—H24	119.3
C11—C10—C12	110.93 (13)	C19—C24—H24	119.3
C11—C10—C7	111.86 (13)	C22—C25—H25A	109.5
C12—C10—C7	109.54 (13)	C22—C25—H25B	109.5
C11—C10—C9	110.30 (13)	H25A—C25—H25B	109.5
C12—C10—C9	109.40 (12)	C22—C25—H25C	109.5
C7—C10—C9	104.61 (13)	H25A—C25—H25C	109.5
N1—C11—C10	112.80 (12)	H25B—C25—H25C	109.5
N1—C11—H11A	109.0	C1—C26—H26A	109.5
C10—C11—H11A	109.0	C1—C26—H26B	109.5
N1—C11—H11B	109.0	H26A—C26—H26B	109.5
C10—C11—H11B	109.0	C1—C26—H26C	109.5
H11A—C11—H11B	107.8	H26A—C26—H26C	109.5
C13—N1—C11	109.16 (12)	H26B—C26—H26C	109.5
C13—N1—C15	109.21 (14)	O2—C12—C14	120.96 (14)
C11—N1—C15	108.43 (13)	O2—C12—C10	120.79 (14)
N1—C13—C14	112.73 (13)	C14—C12—C10	118.21 (13)
N1—C13—H13A	109.0	C9—O1—H1	109.5
C14—C13—H13A	109.0	N1—C15—H15A	109.5
N1—C13—H13B	109.0	N1—C15—H15B	109.5
C14—C13—H13B	109.0	H15A—C15—H15B	109.5
H13A—C13—H13B	107.8	N1—C15—H15C	109.5
C12—C14—C13	110.21 (12)	H15A—C15—H15C	109.5
C12—C14—C18	110.14 (13)	H15B—C15—H15C	109.5
C13—C14—C18	112.64 (14)	C16—O3—H3A	109.5
C12—C14—C16	109.42 (13)	C8—S1—C7	94.46 (8)
C13—C14—C16	110.36 (13)	C17—S2—C18	94.71 (9)
C6—C1—C2—C3	0.7 (4)	C13—C14—C16—C17	−73.29 (17)
C26—C1—C2—C3	178.7 (2)	C18—C14—C16—C17	47.69 (17)
C1—C2—C3—C4	0.5 (3)	O3—C16—C17—S2	84.70 (17)
C2—C3—C4—C5	−1.9 (3)	C14—C16—C17—S2	−32.04 (17)
C2—C3—C4—C7	177.32 (19)	C12—C14—C18—C19	75.91 (18)
C3—C4—C5—C6	2.2 (3)	C13—C14—C18—C19	−47.6 (2)
C7—C4—C5—C6	−177.1 (2)	C16—C14—C18—C19	−167.00 (15)
C2—C1—C6—C5	−0.4 (4)	C12—C14—C18—S2	−158.70 (11)
C26—C1—C6—C5	−178.3 (3)	C13—C14—C18—S2	77.82 (15)
C4—C5—C6—C1	−1.1 (4)	C16—C14—C18—S2	−41.61 (15)
C5—C4—C7—C10	92.4 (2)	C14—C18—C19—C24	88.9 (3)
C3—C4—C7—C10	−86.9 (2)	S2—C18—C19—C24	−33.0 (3)
C5—C4—C7—S1	−145.32 (17)	C14—C18—C19—C20	−94.8 (2)
C3—C4—C7—S1	35.4 (2)	S2—C18—C19—C20	143.26 (19)
S1—C8—C9—O1	−91.31 (17)	C24—C19—C20—C21	−3.9 (4)
S1—C8—C9—C10	29.8 (2)	C18—C19—C20—C21	179.6 (2)
C4—C7—C10—C11	46.91 (19)	C19—C20—C21—C22	0.6 (5)
S1—C7—C10—C11	−78.80 (14)	C20—C21—C22—C23	2.9 (5)
C4—C7—C10—C12	−76.51 (18)	C20—C21—C22—C25	179.4 (3)
S1—C7—C10—C12	157.79 (11)	C21—C22—C23—C24	−3.0 (5)
C4—C7—C10—C9	166.31 (15)	C25—C22—C23—C24	−179.4 (3)
S1—C7—C10—C9	40.61 (14)	C22—C23—C24—C19	−0.4 (5)
O1—C9—C10—C11	−166.28 (14)	C20—C19—C24—C23	3.9 (4)
C8—C9—C10—C11	75.07 (18)	C18—C19—C24—C23	−179.8 (3)
O1—C9—C10—C12	−44.00 (18)	C13—C14—C12—O2	144.04 (15)
C8—C9—C10—C12	−162.66 (15)	C18—C14—C12—O2	19.1 (2)
O1—C9—C10—C7	73.28 (17)	C16—C14—C12—O2	−94.44 (18)
C8—C9—C10—C7	−45.38 (18)	C13—C14—C12—C10	−38.32 (18)
C12—C10—C11—N1	−48.75 (17)	C18—C14—C12—C10	−163.20 (13)
C7—C10—C11—N1	−171.38 (13)	C16—C14—C12—C10	83.21 (16)
C9—C10—C11—N1	72.63 (17)	C11—C10—C12—O2	−144.83 (15)
C10—C11—N1—C13	62.95 (16)	C7—C10—C12—O2	−20.9 (2)
C10—C11—N1—C15	−178.17 (14)	C9—C10—C12—O2	93.27 (17)
C11—N1—C13—C14	−64.23 (16)	C11—C10—C12—C14	37.52 (18)
C15—N1—C13—C14	177.37 (13)	C7—C10—C12—C14	161.49 (13)
N1—C13—C14—C12	50.91 (17)	C9—C10—C12—C14	−84.38 (16)
N1—C13—C14—C18	174.35 (13)	C9—C8—S1—C7	−4.88 (16)
N1—C13—C14—C16	−70.05 (17)	C4—C7—S1—C8	−149.17 (14)
C12—C14—C16—O3	44.99 (18)	C10—C7—S1—C8	−21.24 (14)
C13—C14—C16—O3	166.42 (14)	C16—C17—S2—C18	6.01 (15)
C18—C14—C16—O3	−72.60 (17)	C19—C18—S2—C17	150.01 (14)
C12—C14—C16—C17	165.27 (14)	C14—C18—S2—C17	21.28 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.82	2.16	2.955 (2)	163
O3—H3A···N1^i	0.82	1.99	2.798 (2)	167
C16—H16···O3^ii	0.98	2.39	3.273 (2)	150

Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2.

(II) 13-Benzyl-4,11-dihydroxy-1,8-bis(4-methylphenyl)-2,9-dithia-13-azadispiro[4.1.4⁷.3⁵]tetradecan-6-one

Crystal data

C32H35NO3S2	Z = 2
Mr = 545.73	F(000) = 580
Triclinic, P1	Dx = 1.301 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9803 (6) Å	Cell parameters from 5668 reflections
b = 11.7773 (8) Å	θ = 1.7–26.4°
c = 13.6506 (14) Å	µ = 0.23 mm^−1
α = 105.524 (5)°	T = 293 K
β = 107.215 (5)°	Block, colourless
γ = 103.087 (4)°	0.20 × 0.15 × 0.10 mm
V = 1392.90 (19) Å^3

Data collection

Bruker SMART APEXII area-detector diffractometer	5668 independent reflections
Radiation source: fine-focus sealed tube	4271 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω and φ scans	θmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
Tmin = 0.956, Tmax = 0.978	k = −14→14
20239 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0561P)^2 + 0.7912P] where P = (Fo^2 + 2Fc^2)/3
5668 reflections	(Δ/σ)max = 0.039
349 parameters	Δρmax = 0.30 e Å^−3
1 restraint	Δρmin = −0.50 e Å^−3

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. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	0.8797 (3)	0.6378 (2)	0.1804 (2)	0.0523 (6)
C2	0.7697 (3)	0.5580 (2)	0.1950 (2)	0.0553 (6)
H2	0.7056	0.5894	0.2227	0.066*
C3	0.7519 (2)	0.4328 (2)	0.1697 (2)	0.0476 (5)
H3	0.6769	0.3818	0.1814	0.057*
C4	0.8438 (2)	0.38122 (19)	0.12686 (17)	0.0356 (4)
C5	0.9562 (2)	0.4619 (2)	0.1134 (2)	0.0447 (5)
H5	1.0209	0.4309	0.0861	0.054*
C6	0.9737 (3)	0.5873 (2)	0.1399 (2)	0.0528 (6)
H6	1.0503	0.6391	0.1304	0.063*
C7	0.8278 (2)	0.24410 (19)	0.09546 (17)	0.0373 (4)
H7	0.8458	0.2197	0.0273	0.045*
C8	0.7035 (2)	0.0592 (2)	0.1530 (2)	0.0504 (6)
H8A	0.6998	0.0943	0.2246	0.061*
H8B	0.6416	−0.0281	0.1200	0.061*
C9	0.8627 (2)	0.07220 (19)	0.16339 (18)	0.0406 (5)
H9	0.9133	0.0549	0.2283	0.049*
C10	0.9391 (2)	0.21064 (17)	0.18060 (16)	0.0319 (4)
C11	0.9745 (2)	0.29249 (19)	0.29918 (16)	0.0353 (4)
H11A	1.0086	0.3800	0.3082	0.042*
H11B	0.8854	0.2764	0.3156	0.042*
C12	1.2306 (2)	0.31299 (19)	0.36365 (17)	0.0367 (4)
H12A	1.3110	0.3084	0.4217	0.044*
H12B	1.2495	0.3999	0.3709	0.044*
C13	1.2257 (2)	0.23660 (18)	0.25115 (16)	0.0332 (4)
C14	1.0832 (2)	0.22128 (17)	0.15850 (16)	0.0326 (4)
C15	1.2342 (3)	0.1062 (2)	0.25259 (19)	0.0434 (5)
H15	1.1806	0.0807	0.2969	0.052*
C16	1.3981 (3)	0.1214 (3)	0.3083 (3)	0.0771 (9)
H16A	1.4221	0.0556	0.2641	0.093*
H16B	1.4155	0.1138	0.3797	0.093*
C17	1.3638 (2)	0.2929 (2)	0.22724 (18)	0.0370 (4)
H17	1.3493	0.2396	0.1536	0.044*
C18	1.3963 (2)	0.4256 (2)	0.22939 (17)	0.0359 (4)
C19	1.3530 (3)	0.4447 (2)	0.1302 (2)	0.0473 (5)
H19	1.3093	0.3764	0.0645	0.057*
C20	1.3742 (3)	0.5639 (2)	0.1281 (2)	0.0549 (6)
H20	1.3431	0.5741	0.0607	0.066*
C21	1.4403 (3)	0.6678 (2)	0.2232 (2)	0.0517 (6)
C22	1.4881 (2)	0.6492 (2)	0.3219 (2)	0.0462 (5)
H22	1.5353	0.7179	0.3872	0.055*
C23	1.4670 (2)	0.5305 (2)	0.32530 (18)	0.0407 (5)
H23	1.5007	0.5207	0.3927	0.049*
C24	1.0994 (2)	0.3146 (2)	0.48788 (17)	0.0419 (5)
H24A	1.1076	0.4020	0.5070	0.050*
H24B	1.1883	0.3091	0.5373	0.050*
C25	0.9655 (2)	0.2443 (2)	0.50273 (17)	0.0414 (5)
C26	0.8899 (3)	0.3059 (3)	0.5544 (2)	0.0653 (7)
H26	0.9200	0.3926	0.5789	0.078*
C27	0.7694 (4)	0.2405 (5)	0.5704 (3)	0.0973 (13)
H27	0.7191	0.2835	0.6055	0.117*
C28	0.7242 (4)	0.1134 (5)	0.5352 (3)	0.1005 (14)
H28	0.6438	0.0698	0.5468	0.121*
C29	0.7973 (4)	0.0500 (4)	0.4825 (3)	0.0861 (11)
H29	0.7659	−0.0368	0.4575	0.103*
C30	0.9178 (3)	0.1153 (3)	0.4668 (2)	0.0587 (6)
H30	0.9676	0.0719	0.4314	0.070*
C31	0.8977 (4)	0.7745 (3)	0.2073 (3)	0.0809 (10)
H31A	0.9992	0.8238	0.2536	0.121*
H31B	0.8339	0.7951	0.2448	0.121*
H31C	0.8714	0.7918	0.1405	0.121*
C32	1.4589 (4)	0.7978 (3)	0.2204 (3)	0.0879 (11)
H32A	1.3655	0.8123	0.2075	0.132*
H32B	1.4918	0.8054	0.1623	0.132*
H32C	1.5313	0.8582	0.2894	0.132*
N1	1.08991 (17)	0.26497 (15)	0.37491 (13)	0.0336 (4)
O1	0.8638 (2)	−0.01340 (14)	0.06942 (15)	0.0594 (5)
H1	0.9499	−0.0057	0.0757	0.089*
O2	1.08398 (17)	0.21434 (14)	0.06883 (12)	0.0427 (4)
O3	1.1736 (2)	0.01162 (16)	0.14756 (17)	0.0606 (5)
S1	0.64069 (6)	0.14300 (6)	0.06705 (6)	0.0616 (2)
S2	1.51660 (6)	0.27141 (6)	0.32504 (6)	0.05307 (19)
H3A	1.170 (10)	0.013 (8)	0.087 (3)	0.28 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0624 (15)	0.0476 (13)	0.0453 (14)	0.0226 (12)	0.0122 (12)	0.0202 (11)
C2	0.0549 (15)	0.0619 (15)	0.0620 (16)	0.0323 (13)	0.0272 (13)	0.0255 (13)
C3	0.0361 (11)	0.0606 (14)	0.0571 (15)	0.0189 (10)	0.0224 (11)	0.0301 (12)
C4	0.0296 (10)	0.0438 (11)	0.0346 (11)	0.0125 (8)	0.0090 (8)	0.0193 (9)
C5	0.0390 (12)	0.0499 (12)	0.0545 (14)	0.0153 (10)	0.0240 (11)	0.0255 (11)
C6	0.0541 (14)	0.0488 (13)	0.0579 (15)	0.0095 (11)	0.0229 (12)	0.0272 (12)
C7	0.0288 (10)	0.0433 (11)	0.0362 (11)	0.0075 (8)	0.0079 (8)	0.0174 (9)
C8	0.0362 (12)	0.0482 (13)	0.0552 (15)	−0.0008 (10)	0.0116 (11)	0.0197 (11)
C9	0.0395 (11)	0.0353 (10)	0.0405 (12)	0.0049 (9)	0.0112 (9)	0.0144 (9)
C10	0.0269 (9)	0.0329 (10)	0.0334 (10)	0.0073 (8)	0.0091 (8)	0.0130 (8)
C11	0.0304 (10)	0.0392 (10)	0.0348 (11)	0.0110 (8)	0.0110 (8)	0.0130 (9)
C12	0.0284 (10)	0.0417 (11)	0.0358 (11)	0.0070 (8)	0.0100 (9)	0.0137 (9)
C13	0.0297 (10)	0.0362 (10)	0.0371 (11)	0.0121 (8)	0.0132 (8)	0.0169 (9)
C14	0.0329 (10)	0.0281 (9)	0.0338 (11)	0.0074 (8)	0.0112 (8)	0.0105 (8)
C15	0.0480 (13)	0.0407 (11)	0.0486 (13)	0.0180 (10)	0.0201 (11)	0.0223 (10)
C16	0.0608 (17)	0.0567 (16)	0.111 (3)	0.0266 (14)	0.0117 (17)	0.0439 (17)
C17	0.0308 (10)	0.0460 (11)	0.0412 (12)	0.0162 (9)	0.0170 (9)	0.0197 (9)
C18	0.0243 (9)	0.0473 (11)	0.0417 (12)	0.0123 (8)	0.0154 (9)	0.0211 (10)
C19	0.0397 (12)	0.0549 (13)	0.0420 (13)	0.0062 (10)	0.0117 (10)	0.0216 (11)
C20	0.0470 (13)	0.0650 (16)	0.0535 (15)	0.0112 (12)	0.0117 (12)	0.0370 (13)
C21	0.0387 (12)	0.0509 (13)	0.0675 (17)	0.0115 (10)	0.0173 (12)	0.0303 (13)
C22	0.0345 (11)	0.0456 (12)	0.0534 (14)	0.0078 (9)	0.0158 (10)	0.0159 (11)
C23	0.0293 (10)	0.0534 (13)	0.0411 (12)	0.0103 (9)	0.0137 (9)	0.0220 (10)
C24	0.0373 (11)	0.0495 (12)	0.0340 (11)	0.0089 (9)	0.0123 (9)	0.0139 (9)
C25	0.0357 (11)	0.0583 (13)	0.0329 (11)	0.0170 (10)	0.0127 (9)	0.0196 (10)
C26	0.0576 (16)	0.093 (2)	0.0606 (17)	0.0383 (15)	0.0315 (14)	0.0303 (15)
C27	0.062 (2)	0.177 (4)	0.094 (3)	0.060 (3)	0.054 (2)	0.068 (3)
C28	0.0418 (16)	0.175 (4)	0.093 (3)	0.012 (2)	0.0281 (18)	0.077 (3)
C29	0.069 (2)	0.092 (2)	0.083 (2)	−0.0077 (18)	0.0185 (18)	0.0480 (19)
C30	0.0553 (15)	0.0636 (16)	0.0601 (16)	0.0120 (12)	0.0257 (13)	0.0288 (13)
C31	0.110 (3)	0.0518 (16)	0.078 (2)	0.0338 (17)	0.025 (2)	0.0267 (15)
C32	0.090 (2)	0.0593 (18)	0.110 (3)	0.0150 (17)	0.023 (2)	0.0478 (19)
N1	0.0278 (8)	0.0414 (9)	0.0312 (9)	0.0091 (7)	0.0107 (7)	0.0150 (7)
O1	0.0632 (11)	0.0353 (8)	0.0706 (12)	0.0061 (8)	0.0314 (10)	0.0070 (8)
O2	0.0425 (8)	0.0520 (9)	0.0334 (8)	0.0138 (7)	0.0155 (7)	0.0153 (7)
O3	0.0809 (13)	0.0417 (9)	0.0590 (12)	0.0265 (9)	0.0248 (10)	0.0146 (8)
S1	0.0285 (3)	0.0585 (4)	0.0774 (5)	−0.0016 (3)	−0.0024 (3)	0.0320 (4)
S2	0.0349 (3)	0.0693 (4)	0.0699 (4)	0.0264 (3)	0.0209 (3)	0.0390 (3)

Geometric parameters (Å, º)

C1—C2	1.375 (4)	C16—H16A	0.9700
C1—C6	1.387 (4)	C16—H16B	0.9700
C1—C31	1.508 (4)	C17—C18	1.513 (3)
C2—C3	1.377 (3)	C17—S2	1.823 (2)
C2—H2	0.9300	C17—H17	0.9800
C3—C4	1.390 (3)	C18—C19	1.389 (3)
C3—H3	0.9300	C18—C23	1.390 (3)
C4—C5	1.389 (3)	C19—C20	1.380 (3)
C4—C7	1.513 (3)	C19—H19	0.9300
C5—C6	1.378 (3)	C20—C21	1.377 (4)
C5—H5	0.9300	C20—H20	0.9300
C6—H6	0.9300	C21—C22	1.385 (3)
C7—C10	1.555 (3)	C21—C32	1.512 (4)
C7—S1	1.837 (2)	C22—C23	1.381 (3)
C7—H7	0.9800	C22—H22	0.9300
C8—C9	1.520 (3)	C23—H23	0.9300
C8—S1	1.791 (3)	C24—N1	1.461 (3)
C8—H8A	0.9700	C24—C25	1.504 (3)
C8—H8B	0.9700	C24—H24A	0.9700
C9—O1	1.408 (3)	C24—H24B	0.9700
C9—C10	1.556 (3)	C25—C26	1.371 (3)
C9—H9	0.9800	C25—C30	1.382 (3)
C10—C11	1.532 (3)	C26—C27	1.384 (5)
C10—C14	1.539 (3)	C26—H26	0.9300
C11—N1	1.464 (3)	C27—C28	1.362 (6)
C11—H11A	0.9700	C27—H27	0.9300
C11—H11B	0.9700	C28—C29	1.370 (6)
C12—N1	1.460 (2)	C28—H28	0.9300
C12—C13	1.538 (3)	C29—C30	1.382 (4)
C12—H12A	0.9700	C29—H29	0.9300
C12—H12B	0.9700	C30—H30	0.9300
C13—C14	1.534 (3)	C31—H31A	0.9600
C13—C17	1.553 (3)	C31—H31B	0.9600
C13—C15	1.562 (3)	C31—H31C	0.9600
C14—O2	1.207 (2)	C32—H32A	0.9600
C15—O3	1.410 (3)	C32—H32B	0.9600
C15—C16	1.531 (4)	C32—H32C	0.9600
C15—H15	0.9800	O1—H1	0.8200
C16—S2	1.803 (3)	O3—H3A	0.82 (2)
C2—C1—C6	117.2 (2)	S2—C16—H16A	109.5
C2—C1—C31	121.5 (3)	C15—C16—H16B	109.5
C6—C1—C31	121.3 (3)	S2—C16—H16B	109.5
C1—C2—C3	121.8 (2)	H16A—C16—H16B	108.1
C1—C2—H2	119.1	C18—C17—C13	117.59 (16)
C3—C2—H2	119.1	C18—C17—S2	113.06 (14)
C2—C3—C4	121.2 (2)	C13—C17—S2	104.14 (13)
C2—C3—H3	119.4	C18—C17—H17	107.2
C4—C3—H3	119.4	C13—C17—H17	107.2
C5—C4—C3	117.1 (2)	S2—C17—H17	107.2
C5—C4—C7	119.27 (19)	C19—C18—C23	117.6 (2)
C3—C4—C7	123.64 (19)	C19—C18—C17	118.6 (2)
C6—C5—C4	121.1 (2)	C23—C18—C17	123.76 (19)
C6—C5—H5	119.4	C20—C19—C18	120.8 (2)
C4—C5—H5	119.4	C20—C19—H19	119.6
C5—C6—C1	121.5 (2)	C18—C19—H19	119.6
C5—C6—H6	119.2	C21—C20—C19	121.7 (2)
C1—C6—H6	119.2	C21—C20—H20	119.2
C4—C7—C10	115.31 (16)	C19—C20—H20	119.2
C4—C7—S1	113.35 (14)	C20—C21—C22	117.6 (2)
C10—C7—S1	106.77 (13)	C20—C21—C32	121.4 (3)
C4—C7—H7	107.0	C22—C21—C32	121.0 (3)
C10—C7—H7	107.0	C23—C22—C21	121.3 (2)
S1—C7—H7	107.0	C23—C22—H22	119.3
C9—C8—S1	106.11 (15)	C21—C22—H22	119.3
C9—C8—H8A	110.5	C22—C23—C18	120.9 (2)
S1—C8—H8A	110.5	C22—C23—H23	119.5
C9—C8—H8B	110.5	C18—C23—H23	119.5
S1—C8—H8B	110.5	N1—C24—C25	111.66 (17)
H8A—C8—H8B	108.7	N1—C24—H24A	109.3
O1—C9—C8	110.11 (19)	C25—C24—H24A	109.3
O1—C9—C10	112.94 (17)	N1—C24—H24B	109.3
C8—C9—C10	106.43 (17)	C25—C24—H24B	109.3
O1—C9—H9	109.1	H24A—C24—H24B	107.9
C8—C9—H9	109.1	C26—C25—C30	118.3 (2)
C10—C9—H9	109.1	C26—C25—C24	121.2 (2)
C11—C10—C14	110.28 (15)	C30—C25—C24	120.4 (2)
C11—C10—C7	112.19 (16)	C25—C26—C27	120.8 (3)
C14—C10—C7	110.24 (16)	C25—C26—H26	119.6
C11—C10—C9	108.78 (16)	C27—C26—H26	119.6
C14—C10—C9	108.77 (16)	C28—C27—C26	120.3 (3)
C7—C10—C9	106.46 (15)	C28—C27—H27	119.9
N1—C11—C10	109.70 (16)	C26—C27—H27	119.9
N1—C11—H11A	109.7	C27—C28—C29	119.9 (3)
C10—C11—H11A	109.7	C27—C28—H28	120.1
N1—C11—H11B	109.7	C29—C28—H28	120.1
C10—C11—H11B	109.7	C28—C29—C30	119.8 (4)
H11A—C11—H11B	108.2	C28—C29—H29	120.1
N1—C12—C13	110.40 (16)	C30—C29—H29	120.1
N1—C12—H12A	109.6	C25—C30—C29	120.9 (3)
C13—C12—H12A	109.6	C25—C30—H30	119.6
N1—C12—H12B	109.6	C29—C30—H30	119.6
C13—C12—H12B	109.6	C1—C31—H31A	109.5
H12A—C12—H12B	108.1	C1—C31—H31B	109.5
C14—C13—C12	110.81 (16)	H31A—C31—H31B	109.5
C14—C13—C17	109.88 (16)	C1—C31—H31C	109.5
C12—C13—C17	113.19 (16)	H31A—C31—H31C	109.5
C14—C13—C15	110.49 (16)	H31B—C31—H31C	109.5
C12—C13—C15	108.44 (16)	C21—C32—H32A	109.5
C17—C13—C15	103.81 (16)	C21—C32—H32B	109.5
O2—C14—C13	120.01 (18)	H32A—C32—H32B	109.5
O2—C14—C10	120.85 (18)	C21—C32—H32C	109.5
C13—C14—C10	119.11 (16)	H32A—C32—H32C	109.5
O3—C15—C16	109.4 (2)	H32B—C32—H32C	109.5
O3—C15—C13	114.05 (18)	C12—N1—C24	112.54 (16)
C16—C15—C13	107.70 (18)	C12—N1—C11	108.66 (15)
O3—C15—H15	108.5	C24—N1—C11	111.57 (16)
C16—C15—H15	108.5	C9—O1—H1	109.5
C13—C15—H15	108.5	C15—O3—H3A	132 (6)
C15—C16—S2	110.68 (17)	C8—S1—C7	95.12 (10)
C15—C16—H16A	109.5	C16—S2—C17	91.17 (11)
C6—C1—C2—C3	−0.6 (4)	C17—C13—C15—O3	−83.2 (2)
C31—C1—C2—C3	179.4 (3)	C14—C13—C15—C16	156.2 (2)
C1—C2—C3—C4	−0.7 (4)	C12—C13—C15—C16	−82.2 (2)
C2—C3—C4—C5	1.5 (3)	C17—C13—C15—C16	38.4 (3)
C2—C3—C4—C7	−178.8 (2)	O3—C15—C16—S2	113.2 (2)
C3—C4—C5—C6	−1.0 (3)	C13—C15—C16—S2	−11.3 (3)
C7—C4—C5—C6	179.3 (2)	C14—C13—C17—C18	66.7 (2)
C4—C5—C6—C1	−0.3 (4)	C12—C13—C17—C18	−57.8 (2)
C2—C1—C6—C5	1.2 (4)	C15—C13—C17—C18	−175.15 (18)
C31—C1—C6—C5	−178.9 (2)	C14—C13—C17—S2	−167.34 (13)
C5—C4—C7—C10	78.8 (2)	C12—C13—C17—S2	68.19 (18)
C3—C4—C7—C10	−100.8 (2)	C15—C13—C17—S2	−49.17 (18)
C5—C4—C7—S1	−157.71 (17)	C13—C17—C18—C19	−99.7 (2)
C3—C4—C7—S1	22.6 (3)	S2—C17—C18—C19	138.84 (17)
S1—C8—C9—O1	−80.24 (19)	C13—C17—C18—C23	80.1 (2)
S1—C8—C9—C10	42.5 (2)	S2—C17—C18—C23	−41.3 (2)
C4—C7—C10—C11	35.2 (2)	C23—C18—C19—C20	−2.7 (3)
S1—C7—C10—C11	−91.72 (17)	C17—C18—C19—C20	177.1 (2)
C4—C7—C10—C14	−88.1 (2)	C18—C19—C20—C21	0.9 (4)
S1—C7—C10—C14	144.97 (14)	C19—C20—C21—C22	1.4 (4)
C4—C7—C10—C9	154.07 (17)	C19—C20—C21—C32	−178.1 (3)
S1—C7—C10—C9	27.17 (19)	C20—C21—C22—C23	−1.6 (3)
O1—C9—C10—C11	−163.04 (17)	C32—C21—C22—C23	177.9 (2)
C8—C9—C10—C11	76.0 (2)	C21—C22—C23—C18	−0.3 (3)
O1—C9—C10—C14	−42.9 (2)	C19—C18—C23—C22	2.5 (3)
C8—C9—C10—C14	−163.83 (17)	C17—C18—C23—C22	−177.36 (18)
O1—C9—C10—C7	75.9 (2)	N1—C24—C25—C26	−131.5 (2)
C8—C9—C10—C7	−45.1 (2)	N1—C24—C25—C30	50.1 (3)
C14—C10—C11—N1	−51.4 (2)	C30—C25—C26—C27	0.3 (4)
C7—C10—C11—N1	−174.70 (15)	C24—C25—C26—C27	−178.1 (3)
C9—C10—C11—N1	67.8 (2)	C25—C26—C27—C28	0.1 (5)
N1—C12—C13—C14	48.6 (2)	C26—C27—C28—C29	−0.7 (6)
N1—C12—C13—C17	172.50 (16)	C27—C28—C29—C30	0.8 (5)
N1—C12—C13—C15	−72.9 (2)	C26—C25—C30—C29	−0.1 (4)
C12—C13—C14—O2	148.46 (18)	C24—C25—C30—C29	178.3 (2)
C17—C13—C14—O2	22.6 (2)	C28—C29—C30—C25	−0.4 (5)
C15—C13—C14—O2	−91.3 (2)	C13—C12—N1—C24	166.97 (17)
C12—C13—C14—C10	−33.5 (2)	C13—C12—N1—C11	−69.0 (2)
C17—C13—C14—C10	−159.36 (16)	C25—C24—N1—C12	−167.72 (17)
C15—C13—C14—C10	86.7 (2)	C25—C24—N1—C11	69.8 (2)
C11—C10—C14—O2	−146.97 (18)	C10—C11—N1—C12	70.60 (19)
C7—C10—C14—O2	−22.5 (2)	C10—C11—N1—C24	−164.76 (16)
C9—C10—C14—O2	93.8 (2)	C9—C8—S1—C7	−23.05 (18)
C11—C10—C14—C13	35.0 (2)	C4—C7—S1—C8	−130.77 (16)
C7—C10—C14—C13	159.47 (16)	C10—C7—S1—C8	−2.71 (16)
C9—C10—C14—C13	−84.2 (2)	C15—C16—S2—C17	−15.5 (2)
C14—C13—C15—O3	34.5 (2)	C18—C17—S2—C16	166.52 (18)
C12—C13—C15—O3	156.18 (18)	C13—C17—S2—C16	37.74 (18)

Hydrogen-bond geometry (Å, º)

Cg4 and Cg5 are the centroids of the B (C1–C6) and C (C18–C23) toluyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.82	2.09	2.873 (3)	159
O3—H3A···O1^i	0.82 (6)	2.06 (5)	2.880 (3)	174 (1)
C2—H2···Cg5^ii	0.93	2.80	3.620 (3)	148
C20—H20···Cg4^iii	0.93	2.79	3.616 (3)	149

Symmetry codes: (i) −x+2, −y, −z; (ii) x−1, y, z; (iii) −x+2, −y+1, −z.