3-Benzyl­idene-3′,7′-diphenyl­cyclo­hexa­nespiro-6′-(perhydro-2-thiapyrrolizidine)-5′-spiro-3′′-1H-indole-2,2′′-dione

In the title compound, C₃₇H₃₂N₂O₂S, the two rings of the thia­pyrrolizidine residues each adopt an envelope conformation, whereas the cyclo­hexa­none ring adopts a chair conformation. N—H...O hydrogen bonds connect the mol­ecules into centrosymmetric dimers.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.142
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.64 Ratio
PLAT322_ALERT_2_C Check Hybridisation of  S7     in Main Residue .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

3-Benzylidene-3',7'-diphenylcyclohexanespiro-6'-(perhydro-2-thiapyrrolizine)- 5'-spiro-3''-1H-indole-2,2''-dione

Crystal data

C37H32N2O2S	F(000) = 1200
Mr = 568.71	Dx = 1.301 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5486 reflections
a = 10.0312 (6) Å	θ = 2.4–27.1°
b = 20.8599 (13) Å	µ = 0.15 mm^−1
c = 14.1305 (8) Å	T = 293 K
β = 100.973 (1)°	Block, colourless
V = 2902.7 (3) Å^3	0.35 × 0.24 × 0.16 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4985 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 28.0°, θmin = 1.8°
ω scans	h = −12→12
17503 measured reflections	k = −26→27
6460 independent reflections	l = −18→18

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0816P)^2 + 0.4571P] where P = (Fo^2 + 2Fc^2)/3
6460 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
O1	0.40364 (12)	0.44823 (6)	0.05249 (8)	0.0413 (3)
O2	0.70613 (13)	0.25070 (6)	0.22392 (8)	0.0465 (3)
N1	0.42179 (14)	0.39301 (6)	0.24143 (9)	0.0315 (3)
C2	0.53140 (16)	0.38460 (7)	0.18784 (10)	0.0297 (3)
C3	0.51275 (16)	0.31205 (7)	0.14752 (10)	0.0298 (3)
C4	0.43311 (16)	0.28131 (7)	0.22058 (10)	0.0316 (3)
H4	0.4988	0.2736	0.2803	0.038*
C5	0.34015 (17)	0.33524 (7)	0.24125 (11)	0.0343 (4)
H5	0.2602	0.3377	0.1893	0.041*
C6	0.2951 (2)	0.33057 (9)	0.33865 (13)	0.0489 (5)
H6A	0.2871	0.2861	0.3566	0.059*
H6B	0.2079	0.3514	0.3356	0.059*
S7	0.42397 (6)	0.37036 (2)	0.42458 (3)	0.05545 (17)
C8	0.44012 (18)	0.42906 (8)	0.33030 (11)	0.0360 (4)
H8	0.5329	0.4460	0.3436	0.043*
C9	0.51065 (17)	0.43548 (7)	0.10576 (10)	0.0326 (3)
N10	0.63019 (15)	0.46547 (6)	0.10670 (10)	0.0394 (3)
H10	0.6441	0.4927	0.0639	0.047*
C11	0.72877 (17)	0.44682 (7)	0.18604 (11)	0.0340 (3)
C12	0.85933 (19)	0.46936 (8)	0.21341 (13)	0.0440 (4)
H12	0.8938	0.5003	0.1771	0.053*
C13	0.9378 (2)	0.44463 (9)	0.29665 (14)	0.0488 (5)
H13	1.0266	0.4589	0.3165	0.059*
C14	0.8859 (2)	0.39924 (9)	0.35046 (13)	0.0475 (4)
H14	0.9400	0.3834	0.4064	0.057*
C15	0.75376 (18)	0.37674 (8)	0.32233 (11)	0.0390 (4)
H15	0.7193	0.3461	0.3591	0.047*
C16	0.67456 (17)	0.40052 (7)	0.23907 (10)	0.0311 (3)
C17	0.65271 (17)	0.28090 (7)	0.15335 (11)	0.0336 (3)
C18	0.72237 (18)	0.29028 (8)	0.07009 (12)	0.0381 (4)
C19	0.6355 (2)	0.28523 (9)	−0.02892 (12)	0.0470 (4)
H19A	0.6121	0.2407	−0.0431	0.056*
H19B	0.6862	0.3005	−0.0764	0.056*
C20	0.50734 (19)	0.32415 (9)	−0.03561 (11)	0.0427 (4)
H20A	0.4493	0.3170	−0.0979	0.051*
H20B	0.5303	0.3694	−0.0307	0.051*
C21	0.43063 (17)	0.30643 (8)	0.04371 (10)	0.0356 (4)
H21A	0.3987	0.2626	0.0333	0.043*
H21B	0.3513	0.3338	0.0379	0.043*
C22	0.85360 (19)	0.30639 (8)	0.08990 (13)	0.0438 (4)
H22	0.8941	0.3090	0.1547	0.053*
C23	0.94054 (19)	0.32046 (9)	0.01964 (13)	0.0458 (4)
C24	1.0255 (2)	0.37401 (10)	0.03372 (15)	0.0547 (5)
H24	1.0276	0.3996	0.0879	0.066*
C25	1.1060 (2)	0.38945 (13)	−0.03138 (18)	0.0675 (6)
H25	1.1604	0.4258	−0.0216	0.081*
C26	1.1069 (2)	0.35145 (14)	−0.11109 (18)	0.0722 (7)
H26	1.1618	0.3619	−0.1549	0.087*
C27	1.0260 (2)	0.29821 (13)	−0.12502 (17)	0.0682 (6)
H27	1.0266	0.2722	−0.1784	0.082*
C28	0.9433 (2)	0.28272 (11)	−0.06068 (16)	0.0577 (5)
H28	0.8887	0.2464	−0.0714	0.069*
C29	0.36385 (18)	0.21776 (7)	0.19089 (11)	0.0374 (4)
C30	0.4352 (2)	0.16082 (8)	0.21078 (13)	0.0480 (5)
H30	0.5260	0.1620	0.2410	0.058*
C31	0.3730 (3)	0.10227 (10)	0.18617 (16)	0.0660 (6)
H31	0.4221	0.0646	0.2009	0.079*
C32	0.2403 (3)	0.09934 (11)	0.14055 (17)	0.0710 (7)
H32	0.1991	0.0599	0.1240	0.085*
C33	0.1689 (3)	0.15472 (12)	0.11954 (17)	0.0688 (7)
H33	0.0786	0.1530	0.0881	0.083*
C34	0.2295 (2)	0.21363 (10)	0.14462 (15)	0.0556 (5)
H34	0.1791	0.2510	0.1301	0.067*
C35	0.34223 (18)	0.48505 (8)	0.32667 (13)	0.0399 (4)
C36	0.3229 (2)	0.51500 (11)	0.41025 (16)	0.0608 (6)
H36	0.3619	0.4979	0.4699	0.073*
C37	0.2454 (3)	0.57056 (13)	0.4054 (2)	0.0783 (8)
H37	0.2333	0.5905	0.4620	0.094*
C38	0.1869 (3)	0.59610 (11)	0.3187 (2)	0.0744 (7)
H38	0.1368	0.6338	0.3162	0.089*
C39	0.2021 (2)	0.56609 (11)	0.23523 (18)	0.0667 (6)
H39	0.1607	0.5829	0.1759	0.080*
C40	0.2794 (2)	0.51066 (9)	0.23903 (15)	0.0515 (5)
H40	0.2890	0.4904	0.1821	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0403 (7)	0.0435 (7)	0.0382 (6)	0.0008 (5)	0.0022 (5)	0.0150 (5)
O2	0.0451 (8)	0.0472 (7)	0.0468 (7)	0.0107 (6)	0.0080 (6)	0.0101 (5)
N1	0.0355 (8)	0.0300 (6)	0.0309 (6)	−0.0018 (5)	0.0108 (5)	0.0012 (5)
C2	0.0334 (9)	0.0287 (7)	0.0270 (7)	−0.0008 (6)	0.0060 (6)	0.0044 (5)
C3	0.0331 (9)	0.0287 (7)	0.0277 (7)	−0.0012 (6)	0.0066 (6)	0.0018 (5)
C4	0.0340 (9)	0.0300 (8)	0.0310 (7)	−0.0009 (6)	0.0066 (6)	0.0037 (6)
C5	0.0343 (9)	0.0316 (8)	0.0382 (8)	−0.0017 (6)	0.0096 (7)	0.0043 (6)
C6	0.0572 (13)	0.0410 (10)	0.0562 (11)	0.0016 (8)	0.0305 (9)	0.0058 (8)
S7	0.0833 (4)	0.0522 (3)	0.0334 (2)	0.0111 (2)	0.0176 (2)	0.00707 (19)
C8	0.0401 (10)	0.0362 (8)	0.0325 (7)	0.0010 (7)	0.0086 (7)	−0.0009 (6)
C9	0.0381 (9)	0.0295 (7)	0.0306 (7)	−0.0009 (6)	0.0075 (6)	0.0037 (6)
N10	0.0428 (9)	0.0359 (7)	0.0393 (7)	−0.0063 (6)	0.0077 (6)	0.0134 (6)
C11	0.0366 (9)	0.0308 (8)	0.0350 (7)	−0.0014 (6)	0.0079 (6)	0.0009 (6)
C12	0.0417 (11)	0.0379 (9)	0.0536 (10)	−0.0088 (7)	0.0126 (8)	0.0023 (7)
C13	0.0346 (10)	0.0499 (10)	0.0595 (11)	−0.0078 (8)	0.0031 (8)	−0.0059 (9)
C14	0.0412 (11)	0.0542 (11)	0.0425 (9)	0.0002 (8)	−0.0036 (8)	0.0020 (8)
C15	0.0405 (10)	0.0405 (9)	0.0342 (8)	−0.0019 (7)	0.0031 (7)	0.0057 (6)
C16	0.0343 (9)	0.0286 (7)	0.0312 (7)	−0.0014 (6)	0.0084 (6)	0.0003 (6)
C17	0.0359 (9)	0.0286 (7)	0.0359 (8)	−0.0019 (6)	0.0056 (6)	−0.0026 (6)
C18	0.0407 (10)	0.0355 (8)	0.0397 (8)	0.0013 (7)	0.0118 (7)	−0.0039 (6)
C19	0.0477 (12)	0.0579 (11)	0.0381 (8)	−0.0084 (9)	0.0153 (8)	−0.0117 (8)
C20	0.0467 (11)	0.0540 (10)	0.0275 (7)	−0.0068 (8)	0.0075 (7)	−0.0009 (7)
C21	0.0357 (9)	0.0408 (9)	0.0297 (7)	−0.0032 (7)	0.0046 (6)	0.0004 (6)
C22	0.0391 (11)	0.0467 (10)	0.0464 (9)	0.0021 (8)	0.0098 (7)	−0.0027 (8)
C23	0.0338 (10)	0.0522 (11)	0.0517 (10)	0.0029 (8)	0.0092 (8)	0.0015 (8)
C24	0.0357 (11)	0.0671 (13)	0.0590 (11)	−0.0042 (9)	0.0037 (9)	0.0031 (10)
C25	0.0356 (12)	0.0878 (17)	0.0771 (15)	−0.0108 (11)	0.0057 (10)	0.0194 (13)
C26	0.0393 (13)	0.110 (2)	0.0719 (15)	0.0105 (13)	0.0211 (11)	0.0261 (14)
C27	0.0558 (15)	0.0906 (17)	0.0641 (13)	0.0183 (13)	0.0263 (11)	−0.0013 (12)
C28	0.0492 (13)	0.0601 (13)	0.0679 (13)	0.0049 (9)	0.0214 (10)	−0.0079 (10)
C29	0.0487 (11)	0.0318 (8)	0.0341 (7)	−0.0060 (7)	0.0138 (7)	0.0026 (6)
C30	0.0632 (13)	0.0372 (9)	0.0472 (9)	0.0002 (8)	0.0194 (9)	0.0010 (7)
C31	0.101 (2)	0.0326 (10)	0.0718 (14)	−0.0043 (11)	0.0337 (14)	−0.0047 (9)
C32	0.105 (2)	0.0458 (12)	0.0710 (14)	−0.0336 (13)	0.0379 (14)	−0.0144 (10)
C33	0.0688 (16)	0.0691 (15)	0.0689 (14)	−0.0350 (12)	0.0145 (11)	−0.0094 (11)
C34	0.0534 (13)	0.0466 (11)	0.0649 (12)	−0.0128 (9)	0.0066 (10)	0.0020 (9)
C35	0.0359 (10)	0.0358 (9)	0.0494 (9)	−0.0023 (7)	0.0121 (7)	−0.0049 (7)
C36	0.0606 (14)	0.0657 (13)	0.0553 (11)	0.0120 (11)	0.0089 (10)	−0.0171 (10)
C37	0.0797 (19)	0.0726 (16)	0.0836 (17)	0.0190 (13)	0.0184 (14)	−0.0312 (13)
C38	0.0668 (17)	0.0516 (13)	0.109 (2)	0.0188 (11)	0.0258 (14)	−0.0088 (13)
C39	0.0641 (15)	0.0583 (13)	0.0805 (15)	0.0208 (11)	0.0211 (12)	0.0126 (11)
C40	0.0535 (13)	0.0488 (11)	0.0545 (11)	0.0124 (9)	0.0165 (9)	0.0042 (8)

Geometric parameters (Å, º)

O1—C9	1.2174 (19)	C19—H19B	0.9700
O2—C17	1.2146 (18)	C20—C21	1.521 (2)
N1—C8	1.4450 (19)	C20—H20A	0.9700
N1—C5	1.4568 (19)	C20—H20B	0.9700
N1—C2	1.459 (2)	C21—H21A	0.9700
C2—C16	1.517 (2)	C21—H21B	0.9700
C2—C9	1.5567 (19)	C22—C23	1.470 (3)
C2—C3	1.615 (2)	C22—H22	0.9300
C3—C17	1.535 (2)	C23—C28	1.386 (3)
C3—C21	1.5440 (19)	C23—C24	1.396 (3)
C3—C4	1.559 (2)	C24—C25	1.373 (3)
C4—C29	1.518 (2)	C24—H24	0.9300
C4—C5	1.525 (2)	C25—C26	1.379 (4)
C4—H4	0.9800	C25—H25	0.9300
C5—C6	1.531 (2)	C26—C27	1.368 (4)
C5—H5	0.9800	C26—H26	0.9300
C6—S7	1.799 (2)	C27—C28	1.380 (3)
C6—H6A	0.9700	C27—H27	0.9300
C6—H6B	0.9700	C28—H28	0.9300
S7—C8	1.8392 (16)	C29—C34	1.384 (3)
C8—C35	1.520 (2)	C29—C30	1.388 (2)
C8—H8	0.9800	C30—C31	1.386 (3)
C9—O1	1.2174 (19)	C30—H30	0.9300
C9—N10	1.350 (2)	C31—C32	1.366 (4)
N10—C11	1.401 (2)	C31—H31	0.9300
N10—H10	0.8600	C32—C33	1.362 (4)
C11—C12	1.376 (2)	C32—H32	0.9300
C11—C16	1.395 (2)	C33—C34	1.387 (3)
C12—C13	1.384 (3)	C33—H33	0.9300
C12—H12	0.9300	C34—H34	0.9300
C13—C14	1.377 (3)	C35—C36	1.382 (3)
C13—H13	0.9300	C35—C40	1.385 (3)
C14—C15	1.391 (3)	C36—C37	1.390 (3)
C14—H14	0.9300	C36—H36	0.9300
C15—C16	1.380 (2)	C37—C38	1.362 (4)
C15—H15	0.9300	C37—H37	0.9300
C17—O2	1.2146 (18)	C38—C39	1.369 (3)
C17—C18	1.491 (2)	C38—H38	0.9300
C18—C22	1.336 (2)	C39—C40	1.387 (3)
C18—C19	1.505 (2)	C39—H39	0.9300
C19—C20	1.508 (3)	C40—H40	0.9300
C19—H19A	0.9700
C8—N1—C5	114.24 (12)	C17—C18—C19	116.67 (15)
C8—N1—C2	121.98 (13)	C18—C19—C20	110.89 (14)
C5—N1—C2	112.23 (12)	C18—C19—H19A	109.5
N1—C2—C16	117.67 (12)	C20—C19—H19A	109.5
N1—C2—C9	107.31 (12)	C18—C19—H19B	109.5
C16—C2—C9	100.75 (12)	C20—C19—H19B	109.5
N1—C2—C3	104.34 (12)	H19A—C19—H19B	108.0
C16—C2—C3	114.15 (12)	C19—C20—C21	111.57 (14)
C9—C2—C3	112.69 (11)	C19—C20—H20A	109.3
C17—C3—C21	109.63 (12)	C21—C20—H20A	109.3
C17—C3—C4	111.66 (12)	C19—C20—H20B	109.3
C21—C3—C4	110.49 (13)	C21—C20—H20B	109.3
C17—C3—C2	109.53 (12)	H20A—C20—H20B	108.0
C21—C3—C2	114.29 (12)	C20—C21—C3	115.36 (14)
C4—C3—C2	101.03 (11)	C20—C21—H21A	108.4
C29—C4—C5	115.65 (14)	C3—C21—H21A	108.4
C29—C4—C3	116.20 (12)	C20—C21—H21B	108.4
C5—C4—C3	103.45 (12)	C3—C21—H21B	108.4
C29—C4—H4	107.0	H21A—C21—H21B	107.5
C5—C4—H4	107.0	C18—C22—C23	126.61 (17)
C3—C4—H4	107.0	C18—C22—H22	116.7
N1—C5—C4	104.28 (13)	C23—C22—H22	116.7
N1—C5—C6	108.23 (13)	C28—C23—C24	117.67 (19)
C4—C5—C6	114.91 (13)	C28—C23—C22	123.13 (18)
N1—C5—H5	109.7	C24—C23—C22	119.20 (18)
C4—C5—H5	109.7	C25—C24—C23	120.9 (2)
C6—C5—H5	109.7	C25—C24—H24	119.6
C5—C6—S7	106.29 (13)	C23—C24—H24	119.6
C5—C6—H6A	110.5	C24—C25—C26	120.6 (2)
S7—C6—H6A	110.5	C24—C25—H25	119.7
C5—C6—H6B	110.5	C26—C25—H25	119.7
S7—C6—H6B	110.5	C27—C26—C25	119.3 (2)
H6A—C6—H6B	108.7	C27—C26—H26	120.4
C6—S7—C8	88.23 (8)	C25—C26—H26	120.4
N1—C8—C35	113.32 (13)	C26—C27—C28	120.6 (2)
N1—C8—S7	105.60 (10)	C26—C27—H27	119.7
C35—C8—S7	112.98 (12)	C28—C27—H27	119.7
N1—C8—H8	108.2	C27—C28—C23	121.0 (2)
C35—C8—H8	108.2	C27—C28—H28	119.5
S7—C8—H8	108.2	C23—C28—H28	119.5
O1—C9—N10	125.57 (14)	C34—C29—C30	117.44 (16)
O1—C9—N10	125.57 (14)	C34—C29—C4	122.56 (15)
O1—C9—N10	125.57 (14)	C30—C29—C4	120.00 (16)
O1—C9—N10	125.57 (14)	C31—C30—C29	120.9 (2)
O1—C9—C2	125.93 (14)	C31—C30—H30	119.6
O1—C9—C2	125.93 (14)	C29—C30—H30	119.6
O1—C9—C2	125.93 (14)	C32—C31—C30	120.7 (2)
O1—C9—C2	125.93 (14)	C32—C31—H31	119.7
N10—C9—C2	108.42 (13)	C30—C31—H31	119.7
C9—N10—C11	111.67 (13)	C33—C32—C31	119.4 (2)
C9—N10—H10	124.2	C33—C32—H32	120.3
C11—N10—H10	124.2	C31—C32—H32	120.3
C12—C11—C16	122.22 (15)	C32—C33—C34	120.6 (2)
C12—C11—N10	128.24 (15)	C32—C33—H33	119.7
C16—C11—N10	109.52 (14)	C34—C33—H33	119.7
C11—C12—C13	117.91 (16)	C29—C34—C33	121.1 (2)
C11—C12—H12	121.0	C29—C34—H34	119.5
C13—C12—H12	121.0	C33—C34—H34	119.5
C14—C13—C12	120.81 (18)	C36—C35—C40	118.39 (18)
C14—C13—H13	119.6	C36—C35—C8	120.87 (16)
C12—C13—H13	119.6	C40—C35—C8	120.50 (16)
C13—C14—C15	120.92 (17)	C35—C36—C37	120.2 (2)
C13—C14—H14	119.5	C35—C36—H36	119.9
C15—C14—H14	119.5	C37—C36—H36	119.9
C16—C15—C14	119.00 (16)	C38—C37—C36	120.8 (2)
C16—C15—H15	120.5	C38—C37—H37	119.6
C14—C15—H15	120.5	C36—C37—H37	119.6
C15—C16—C11	119.13 (15)	C37—C38—C39	119.8 (2)
C15—C16—C2	131.84 (15)	C37—C38—H38	120.1
C11—C16—C2	109.01 (13)	C39—C38—H38	120.1
O2—C17—C18	121.06 (15)	C38—C39—C40	120.0 (2)
O2—C17—C3	121.32 (14)	C38—C39—H39	120.0
O2—C17—C3	121.32 (14)	C40—C39—H39	120.0
C18—C17—C3	117.60 (13)	C35—C40—C39	120.8 (2)
C22—C18—C17	117.31 (15)	C35—C40—H40	119.6
C22—C18—C19	125.86 (16)	C39—C40—H40	119.6
C8—N1—C2—C16	14.62 (19)	C12—C13—C14—C15	0.4 (3)
C5—N1—C2—C16	−126.46 (14)	C13—C14—C15—C16	0.1 (3)
C8—N1—C2—C9	−97.95 (15)	C14—C15—C16—C11	−0.6 (3)
C5—N1—C2—C9	120.97 (13)	C14—C15—C16—C2	177.53 (17)
C8—N1—C2—C3	142.27 (13)	C12—C11—C16—C15	0.5 (2)
C5—N1—C2—C3	1.19 (15)	N10—C11—C16—C15	−178.14 (15)
N1—C2—C3—C17	−141.23 (12)	C12—C11—C16—C2	−177.98 (15)
C16—C2—C3—C17	−11.46 (16)	N10—C11—C16—C2	3.35 (18)
C9—C2—C3—C17	102.68 (14)	N1—C2—C16—C15	58.9 (2)
N1—C2—C3—C21	95.31 (14)	C9—C2—C16—C15	175.14 (17)
C16—C2—C3—C21	−134.91 (14)	C3—C2—C16—C15	−63.8 (2)
C9—C2—C3—C21	−20.77 (19)	N1—C2—C16—C11	−122.80 (14)
N1—C2—C3—C4	−23.32 (13)	C9—C2—C16—C11	−6.61 (16)
C16—C2—C3—C4	106.46 (13)	C3—C2—C16—C11	114.42 (14)
C9—C2—C3—C4	−139.40 (13)	O2—O2—C17—C18	0.00 (9)
C17—C3—C4—C29	−79.50 (16)	O2—O2—C17—C3	0.00 (7)
C21—C3—C4—C29	42.80 (18)	C21—C3—C17—O2	−142.48 (15)
C2—C3—C4—C29	164.15 (13)	C4—C3—C17—O2	−19.7 (2)
C17—C3—C4—C5	152.65 (12)	C2—C3—C17—O2	91.37 (17)
C21—C3—C4—C5	−85.06 (14)	C21—C3—C17—O2	−142.48 (15)
C2—C3—C4—C5	36.29 (14)	C4—C3—C17—O2	−19.7 (2)
C8—N1—C5—C4	−121.97 (14)	C2—C3—C17—O2	91.37 (17)
C2—N1—C5—C4	22.27 (15)	C21—C3—C17—C18	38.88 (18)
C8—N1—C5—C6	0.80 (19)	C4—C3—C17—C18	161.66 (13)
C2—N1—C5—C6	145.05 (14)	C2—C3—C17—C18	−87.28 (15)
C29—C4—C5—N1	−164.93 (12)	O2—C17—C18—C22	−44.6 (2)
C3—C4—C5—N1	−36.73 (14)	O2—C17—C18—C22	−44.6 (2)
C29—C4—C5—C6	76.77 (18)	C3—C17—C18—C22	134.01 (16)
C3—C4—C5—C6	−155.03 (14)	O2—C17—C18—C19	139.55 (17)
N1—C5—C6—S7	−28.39 (16)	O2—C17—C18—C19	139.55 (17)
C4—C5—C6—S7	87.67 (15)	C3—C17—C18—C19	−41.8 (2)
C5—C6—S7—C8	36.97 (12)	C22—C18—C19—C20	−127.71 (19)
C5—N1—C8—C35	−97.80 (16)	C17—C18—C19—C20	47.7 (2)
C2—N1—C8—C35	121.82 (15)	C18—C19—C20—C21	−53.7 (2)
C5—N1—C8—S7	26.38 (16)	C19—C20—C21—C3	55.96 (19)
C2—N1—C8—S7	−114.00 (13)	C17—C3—C21—C20	−46.37 (18)
C6—S7—C8—N1	−36.43 (12)	C4—C3—C21—C20	−169.85 (14)
C6—S7—C8—C35	87.96 (13)	C2—C3—C21—C20	77.03 (19)
O1—O1—C9—O1	0.00 (3)	C17—C18—C22—C23	−177.4 (2)
O1—O1—C9—O1	0.00 (3)	C19—C18—C22—C23	−2.0 (3)
O1—O1—C9—O1	0.00 (3)	C18—C22—C23—C28	−45.9 (3)
O1—O1—C9—O1	0.00 (3)	C18—C22—C23—C24	134.5 (2)
O1—O1—C9—O1	0.00 (3)	C28—C23—C24—C25	1.7 (3)
O1—O1—C9—O1	0.00 (3)	C22—C23—C24—C25	−178.63 (19)
O1—O1—C9—N10	0.00 (7)	C23—C24—C25—C26	−1.5 (3)
O1—O1—C9—N10	0.00 (7)	C24—C25—C26—C27	0.3 (3)
O1—O1—C9—N10	0.00 (7)	C25—C26—C27—C28	0.5 (4)
O1—O1—C9—C2	0.000 (18)	C26—C27—C28—C23	−0.2 (3)
O1—O1—C9—C2	0.000 (18)	C24—C23—C28—C27	−0.9 (3)
O1—O1—C9—C2	0.000 (18)	C22—C23—C28—C27	179.48 (19)
N1—C2—C9—O1	−45.4 (2)	C5—C4—C29—C34	27.7 (2)
C16—C2—C9—O1	−169.06 (16)	C3—C4—C29—C34	−93.9 (2)
C3—C2—C9—O1	68.9 (2)	C5—C4—C29—C30	−151.67 (15)
N1—C2—C9—O1	−45.4 (2)	C3—C4—C29—C30	86.74 (18)
C16—C2—C9—O1	−169.06 (16)	C34—C29—C30—C31	−0.8 (3)
C3—C2—C9—O1	68.9 (2)	C4—C29—C30—C31	178.58 (17)
N1—C2—C9—O1	−45.4 (2)	C29—C30—C31—C32	0.9 (3)
C16—C2—C9—O1	−169.06 (16)	C30—C31—C32—C33	−0.2 (3)
C3—C2—C9—O1	68.9 (2)	C31—C32—C33—C34	−0.4 (4)
N1—C2—C9—O1	−45.4 (2)	C30—C29—C34—C33	0.2 (3)
C16—C2—C9—O1	−169.06 (16)	C4—C29—C34—C33	−179.20 (19)
C3—C2—C9—O1	68.9 (2)	C32—C33—C34—C29	0.4 (4)
N1—C2—C9—N10	131.52 (13)	N1—C8—C35—C36	164.47 (18)
C16—C2—C9—N10	7.87 (16)	S7—C8—C35—C36	44.4 (2)
C3—C2—C9—N10	−114.19 (14)	N1—C8—C35—C40	−21.1 (2)
O1—C9—N10—C11	170.41 (16)	S7—C8—C35—C40	−141.19 (16)
O1—C9—N10—C11	170.41 (16)	C40—C35—C36—C37	−1.9 (3)
O1—C9—N10—C11	170.41 (16)	C8—C35—C36—C37	172.6 (2)
O1—C9—N10—C11	170.41 (16)	C35—C36—C37—C38	0.3 (4)
C2—C9—N10—C11	−6.54 (18)	C36—C37—C38—C39	1.4 (4)
C9—N10—C11—C12	−176.43 (17)	C37—C38—C39—C40	−1.4 (4)
C9—N10—C11—C16	2.14 (19)	C36—C35—C40—C39	1.9 (3)
C16—C11—C12—C13	0.0 (3)	C8—C35—C40—C39	−172.67 (19)
N10—C11—C12—C13	178.39 (17)	C38—C39—C40—C35	−0.2 (4)
C11—C12—C13—C14	−0.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2	0.98	2.41	2.804 (2)	103
C20—H20B···O1	0.97	2.50	3.134 (2)	122
C21—H21B···O1	0.97	2.44	2.975 (2)	114
C40—H40···O1	0.93	2.50	3.384 (2)	159
N10—H10···O1^i	0.86	2.04	2.851 (2)	157
C25—H25···O1^ii	0.93	2.51	3.236 (3)	135

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