1,9′-Dimethyl-2′,4′-diphenyl-4′,9′-dihydro-2′H-spiro­[indoline-3,3′-thio­pyrano[2,3-b]indole]-2-thione

The title compound, C₃₂H₂₆N₂S₂, is a new spiro thio­oxindole derivative which was synthesized with the aim that it might be effective in treating a number of diseases. In spite of the existence of the Csp³ atom, the thio­oxindole group is almost planar. There are a number of intra­molecular C—H...S hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.121
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c   ....    P21/a
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.80 Ratio
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10    ..  S2      ..       2.94 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18    ..  S2      ..       2.89 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C10    ..  S2      ..      99.36 Deg.

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

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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1,9'-Dimethyl-2',4'-diphenyl-4',9'-dihydro-2'H-spiro[indoline-3,3'- thiopyrano[2,3-b]indole]-2-thione

Crystal data

C32H26N2S2	F(000) = 1056
Mr = 502.67	Dx = 1.29 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
a = 11.9699 (13) Å	Cell parameters from 2000 reflections
b = 12.3375 (15) Å	θ = 2.0–26.8°
c = 17.8027 (18) Å	µ = 0.23 mm^−1
β = 100.192 (8)°	T = 298 K
V = 2587.6 (5) Å^3	Prism, pale yellow
Z = 4	0.6 × 0.55 × 0.3 mm

Data collection

Stoe IPDS-II diffractometer	5408 independent reflections
Radiation source: fine-focus sealed tube	4680 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 0.15 mm pixels mm^-1	θmax = 26.8°, θmin = 2.0°
rotation method scans	h = −15→15
Absorption correction: numerical shape of crystal determined optically	k = −13→15
Tmin = 0.865, Tmax = 0.945	l = −20→22
12356 measured reflections

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) = 0.121	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0553P)^2 + 0.7891P] where P = (Fo^2 + 2Fc^2)/3
5408 reflections	(Δ/σ)max = 0.024
327 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Experimental. ¹HNMR (CDCl₃) δ 3.40 (s, 3H), 3.83 (s, 3H), 5.30 (s, 1H), 5.50 (s, 1H), 6.21 (d, J=8.0 Hz, 1H), 6.48 (d, J=7.9 Hz, 1H), 6.60 (d, J=7.8 Hz, 1H), 6.70 (t, J=7.6 Hz, 1H), 6.78 (t, J=7.6 Hz, 1H), 6.84 (d, J=7.5 Hz, 2H), 7.01–7.05 (m, 3H), 7.12–7.21 (m, 4H), 7.28 (d, J=7.8 Hz, 1H), 7.33 (d, J=8.2 Hz, 1H), 7.54 (d, J=7.6 Hz, 1H), 7.93 (d, J=7.5 Hz, 1H); ¹³CNMR (CDCl₃) δ 30.5(CH₃), 31.4(CH₃), 52.3(CH), 55.6(CH), 66.4(C), 108.4(CH), 108.8(C), 109.1(CH), 119.3(CH), 119.9(CH), 121.1(CH), 123.5(CH), 126.9(CH), 127.1(CH), 127.5(CH), 127.8(C), 127.9(2CH), 128.8(CH), 128.9(2CH), 129.9(2CH), 130.7(CH), 130.9(C), 131.6(CH), 131.9(C), 135.2(C), 137.7(C), 138.1(C), 146.3(C), 204.3(C).

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. The structure was solved by direct methods. 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
C1	0.62628 (14)	0.58810 (17)	0.89010 (13)	0.0581 (5)
H1C	0.6598	0.5544	0.9374	0.07*
H1B	0.6603	0.6579	0.8863	0.07*
H1A	0.6388	0.5434	0.8482	0.07*
C2	0.45345 (14)	0.62980 (13)	0.94784 (10)	0.0428 (4)
C3	0.50160 (16)	0.65208 (16)	1.02351 (11)	0.0532 (4)
H3	0.5795	0.6465	1.0405	0.064*
C4	0.42985 (19)	0.68252 (16)	1.07190 (11)	0.0593 (5)
H4	0.4598	0.6988	1.1225	0.071*
C5	0.31249 (18)	0.68959 (16)	1.04674 (11)	0.0553 (4)
H5	0.2661	0.7113	1.0807	0.066*
C6	0.26445 (15)	0.66507 (14)	0.97264 (10)	0.0460 (4)
H6	0.1862	0.669	0.9568	0.055*
C7	0.33485 (13)	0.63410 (12)	0.92128 (9)	0.0398 (3)
C8	0.31615 (12)	0.60537 (12)	0.84153 (9)	0.0379 (3)
C9	0.42192 (13)	0.58723 (13)	0.82413 (10)	0.0407 (3)
C10	0.31876 (13)	0.58031 (14)	0.67646 (10)	0.0420 (4)
H10	0.3102	0.6592	0.6728	0.05*
C11	0.32798 (14)	0.53964 (16)	0.59740 (10)	0.0476 (4)
C12	0.33181 (19)	0.43066 (19)	0.57931 (13)	0.0639 (5)
H12	0.3267	0.3787	0.6164	0.077*
C13	0.3432 (2)	0.3980 (3)	0.50635 (14)	0.0784 (7)
H13	0.3444	0.3246	0.4948	0.094*
C14	0.3524 (2)	0.4733 (3)	0.45163 (13)	0.0850 (9)
H14	0.3609	0.4513	0.403	0.102*
C15	0.3493 (2)	0.5809 (3)	0.46858 (13)	0.0839 (8)
H15	0.3553	0.632	0.4311	0.101*
C16	0.33711 (16)	0.6153 (2)	0.54134 (12)	0.0632 (5)
H16	0.3351	0.6889	0.5522	0.076*
C17	0.21727 (12)	0.53655 (13)	0.71157 (9)	0.0377 (3)
C18	0.20667 (12)	0.60497 (13)	0.78491 (9)	0.0370 (3)
H18	0.1932	0.6801	0.7678	0.044*
C19	0.10447 (12)	0.57187 (13)	0.81991 (9)	0.0383 (3)
C20	0.10713 (15)	0.48337 (14)	0.86834 (10)	0.0463 (4)
H20	0.172	0.4405	0.8783	0.056*
C21	0.01470 (17)	0.45794 (16)	0.90200 (13)	0.0573 (5)
H21	0.0178	0.3985	0.9344	0.069*
C22	−0.08206 (17)	0.52100 (19)	0.88744 (15)	0.0683 (6)
H22	−0.1441	0.5046	0.9103	0.082*
C23	−0.08624 (16)	0.60836 (19)	0.83886 (15)	0.0671 (6)
H23	−0.1517	0.6504	0.8284	0.08*
C24	0.00646 (14)	0.63390 (15)	0.80558 (11)	0.0497 (4)
H24	0.003	0.6934	0.7732	0.06*
C25	0.21476 (13)	0.41578 (13)	0.72498 (9)	0.0404 (3)
C26	0.29154 (16)	0.34506 (15)	0.76711 (10)	0.0490 (4)
H26	0.3597	0.3708	0.7946	0.059*
C27	0.2655 (2)	0.23537 (17)	0.76770 (13)	0.0678 (6)
H27	0.3178	0.1873	0.7945	0.081*
C28	0.1645 (3)	0.1972 (2)	0.72960 (15)	0.0799 (7)
H28	0.1486	0.1236	0.7316	0.096*
C29	0.0853 (2)	0.2653 (2)	0.68811 (15)	0.0764 (7)
H29	0.0158	0.2392	0.6628	0.092*
C30	0.11357 (16)	0.37518 (17)	0.68555 (10)	0.0526 (4)
C31	−0.0617 (2)	0.4452 (3)	0.59926 (18)	0.1038 (11)
H31A	−0.1099	0.4105	0.6297	0.125*
H31B	−0.0566	0.4009	0.5556	0.125*
H31C	−0.0928	0.5146	0.5825	0.125*
C32	0.10721 (14)	0.55550 (17)	0.65434 (10)	0.0499 (4)
N1	0.50500 (11)	0.60107 (12)	0.88774 (9)	0.0445 (3)
N2	0.05138 (13)	0.45966 (17)	0.64472 (9)	0.0605 (4)
S1	0.45664 (3)	0.55353 (4)	0.73608 (3)	0.04850 (14)
S2	0.06450 (5)	0.67203 (6)	0.61461 (3)	0.0765 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0306 (8)	0.0587 (11)	0.0819 (14)	−0.0029 (7)	0.0015 (8)	−0.0088 (10)
C2	0.0426 (8)	0.0349 (8)	0.0487 (9)	−0.0023 (6)	0.0020 (7)	0.0001 (7)
C3	0.0514 (10)	0.0484 (10)	0.0538 (10)	−0.0047 (8)	−0.0067 (8)	0.0002 (8)
C4	0.0740 (13)	0.0547 (11)	0.0441 (10)	−0.0050 (9)	−0.0032 (9)	−0.0033 (8)
C5	0.0704 (12)	0.0525 (10)	0.0442 (9)	0.0045 (9)	0.0136 (9)	−0.0024 (8)
C6	0.0499 (9)	0.0434 (9)	0.0452 (9)	0.0032 (7)	0.0100 (7)	−0.0006 (7)
C7	0.0405 (8)	0.0338 (7)	0.0441 (8)	0.0003 (6)	0.0052 (6)	0.0003 (6)
C8	0.0331 (7)	0.0374 (8)	0.0435 (8)	−0.0007 (6)	0.0075 (6)	−0.0020 (6)
C9	0.0332 (7)	0.0394 (8)	0.0494 (9)	−0.0021 (6)	0.0073 (6)	−0.0032 (7)
C10	0.0385 (8)	0.0428 (8)	0.0468 (9)	0.0017 (6)	0.0132 (7)	0.0039 (7)
C11	0.0362 (8)	0.0645 (11)	0.0438 (9)	0.0009 (7)	0.0114 (7)	0.0042 (8)
C12	0.0691 (13)	0.0704 (13)	0.0582 (12)	0.0044 (10)	0.0278 (10)	−0.0053 (10)
C13	0.0678 (13)	0.107 (2)	0.0646 (14)	−0.0017 (13)	0.0229 (11)	−0.0247 (14)
C14	0.0557 (12)	0.155 (3)	0.0446 (11)	−0.0051 (15)	0.0106 (9)	−0.0158 (15)
C15	0.0640 (14)	0.141 (3)	0.0470 (12)	−0.0063 (15)	0.0108 (10)	0.0245 (15)
C16	0.0499 (10)	0.0876 (15)	0.0529 (11)	−0.0035 (10)	0.0111 (9)	0.0164 (11)
C17	0.0308 (7)	0.0444 (8)	0.0381 (8)	0.0022 (6)	0.0066 (6)	0.0029 (6)
C18	0.0314 (7)	0.0373 (8)	0.0427 (8)	0.0028 (6)	0.0079 (6)	0.0009 (6)
C19	0.0329 (7)	0.0401 (8)	0.0429 (8)	0.0008 (6)	0.0092 (6)	−0.0056 (6)
C20	0.0449 (9)	0.0442 (9)	0.0530 (10)	0.0048 (7)	0.0174 (7)	0.0002 (7)
C21	0.0612 (11)	0.0490 (10)	0.0684 (12)	−0.0042 (8)	0.0299 (10)	0.0010 (9)
C22	0.0497 (10)	0.0675 (13)	0.0976 (17)	−0.0027 (9)	0.0402 (11)	−0.0020 (12)
C23	0.0408 (9)	0.0679 (13)	0.0981 (17)	0.0126 (9)	0.0275 (10)	0.0020 (12)
C24	0.0388 (8)	0.0503 (10)	0.0621 (11)	0.0079 (7)	0.0143 (8)	0.0006 (8)
C25	0.0420 (8)	0.0444 (8)	0.0374 (8)	−0.0045 (6)	0.0139 (6)	−0.0049 (7)
C26	0.0612 (10)	0.0443 (9)	0.0438 (9)	0.0034 (8)	0.0154 (8)	0.0024 (7)
C27	0.1074 (18)	0.0459 (10)	0.0577 (12)	0.0020 (11)	0.0350 (12)	0.0048 (9)
C28	0.123 (2)	0.0512 (12)	0.0748 (15)	−0.0232 (14)	0.0435 (16)	−0.0077 (11)
C29	0.0808 (15)	0.0822 (16)	0.0712 (14)	−0.0407 (14)	0.0267 (12)	−0.0280 (13)
C30	0.0497 (9)	0.0661 (12)	0.0442 (9)	−0.0149 (9)	0.0143 (8)	−0.0139 (8)
C31	0.0527 (13)	0.160 (3)	0.0864 (19)	−0.0185 (16)	−0.0201 (13)	−0.016 (2)
C32	0.0371 (8)	0.0762 (13)	0.0365 (8)	0.0091 (8)	0.0066 (7)	0.0030 (8)
N1	0.0309 (6)	0.0446 (8)	0.0558 (8)	−0.0025 (5)	0.0018 (6)	−0.0029 (6)
N2	0.0388 (8)	0.0913 (13)	0.0484 (9)	−0.0087 (8)	−0.0005 (7)	−0.0122 (9)
S1	0.0327 (2)	0.0608 (3)	0.0541 (3)	0.00021 (17)	0.01321 (17)	−0.0086 (2)
S2	0.0651 (3)	0.1012 (5)	0.0623 (3)	0.0352 (3)	0.0088 (3)	0.0294 (3)

Geometric parameters (Å, º)

C1—N1	1.454 (2)	C16—H16	0.93
C1—H1C	0.96	C17—C25	1.510 (2)
C1—H1B	0.96	C17—C32	1.534 (2)
C1—H1A	0.96	C17—C18	1.579 (2)
C2—N1	1.373 (2)	C18—C19	1.524 (2)
C2—C3	1.396 (3)	C18—H18	0.98
C2—C7	1.416 (2)	C19—C24	1.386 (2)
C3—C4	1.372 (3)	C19—C20	1.388 (2)
C3—H3	0.93	C20—C21	1.384 (2)
C4—C5	1.400 (3)	C20—H20	0.93
C4—H4	0.93	C21—C22	1.381 (3)
C5—C6	1.376 (3)	C21—H21	0.93
C5—H5	0.93	C22—C23	1.377 (3)
C6—C7	1.402 (2)	C22—H22	0.93
C6—H6	0.93	C23—C24	1.384 (3)
C7—C8	1.442 (2)	C23—H23	0.93
C8—C9	1.374 (2)	C24—H24	0.93
C8—C18	1.505 (2)	C25—C30	1.382 (2)
C9—N1	1.379 (2)	C25—C26	1.387 (2)
C9—S1	1.7416 (17)	C26—C27	1.389 (3)
C10—C11	1.517 (2)	C26—H26	0.93
C10—C17	1.558 (2)	C27—C28	1.361 (4)
C10—S1	1.8275 (17)	C27—H27	0.93
C10—H10	0.98	C28—C29	1.379 (4)
C11—C16	1.385 (3)	C28—H28	0.93
C11—C12	1.385 (3)	C29—C30	1.400 (3)
C12—C13	1.389 (3)	C29—H29	0.93
C12—H12	0.93	C30—N2	1.406 (3)
C13—C14	1.364 (4)	C31—N2	1.460 (3)
C13—H13	0.93	C31—H31A	0.96
C14—C15	1.363 (4)	C31—H31B	0.96
C14—H14	0.93	C31—H31C	0.96
C15—C16	1.395 (4)	C32—N2	1.354 (3)
C15—H15	0.93	C32—S2	1.643 (2)
N1—C1—H1C	109.5	C10—C17—C18	109.21 (13)
N1—C1—H1B	109.5	C8—C18—C19	113.20 (13)
H1C—C1—H1B	109.5	C8—C18—C17	111.57 (12)
N1—C1—H1A	109.5	C19—C18—C17	112.50 (12)
H1C—C1—H1A	109.5	C8—C18—H18	106.3
H1B—C1—H1A	109.5	C19—C18—H18	106.3
N1—C2—C3	129.59 (16)	C17—C18—H18	106.3
N1—C2—C7	108.17 (14)	C24—C19—C20	118.31 (15)
C3—C2—C7	122.24 (17)	C24—C19—C18	119.44 (15)
C4—C3—C2	117.55 (17)	C20—C19—C18	122.21 (14)
C4—C3—H3	121.2	C21—C20—C19	120.99 (16)
C2—C3—H3	121.2	C21—C20—H20	119.5
C3—C4—C5	121.36 (18)	C19—C20—H20	119.5
C3—C4—H4	119.3	C22—C21—C20	119.94 (19)
C5—C4—H4	119.3	C22—C21—H21	120
C6—C5—C4	121.23 (18)	C20—C21—H21	120
C6—C5—H5	119.4	C23—C22—C21	119.65 (18)
C4—C5—H5	119.4	C23—C22—H22	120.2
C5—C6—C7	119.19 (17)	C21—C22—H22	120.2
C5—C6—H6	120.4	C22—C23—C24	120.29 (18)
C7—C6—H6	120.4	C22—C23—H23	119.9
C6—C7—C2	118.39 (15)	C24—C23—H23	119.9
C6—C7—C8	134.65 (15)	C23—C24—C19	120.82 (18)
C2—C7—C8	106.94 (14)	C23—C24—H24	119.6
C9—C8—C7	105.87 (14)	C19—C24—H24	119.6
C9—C8—C18	125.19 (14)	C30—C25—C26	118.94 (17)
C7—C8—C18	128.70 (13)	C30—C25—C17	108.51 (15)
C8—C9—N1	110.74 (15)	C26—C25—C17	132.55 (15)
C8—C9—S1	128.17 (13)	C25—C26—C27	119.3 (2)
N1—C9—S1	121.09 (12)	C25—C26—H26	120.4
C11—C10—C17	116.60 (14)	C27—C26—H26	120.4
C11—C10—S1	105.83 (11)	C28—C27—C26	120.9 (2)
C17—C10—S1	113.11 (11)	C28—C27—H27	119.5
C11—C10—H10	106.9	C26—C27—H27	119.5
C17—C10—H10	106.9	C27—C28—C29	121.5 (2)
S1—C10—H10	106.9	C27—C28—H28	119.3
C16—C11—C12	118.46 (19)	C29—C28—H28	119.3
C16—C11—C10	118.29 (19)	C28—C29—C30	117.4 (2)
C12—C11—C10	123.21 (17)	C28—C29—H29	121.3
C11—C12—C13	120.7 (2)	C30—C29—H29	121.3
C11—C12—H12	119.6	C25—C30—C29	122.0 (2)
C13—C12—H12	119.6	C25—C30—N2	109.28 (17)
C14—C13—C12	120.3 (3)	C29—C30—N2	128.72 (19)
C14—C13—H13	119.9	N2—C31—H31A	109.5
C12—C13—H13	119.9	N2—C31—H31B	109.5
C15—C14—C13	119.7 (2)	H31A—C31—H31B	109.5
C15—C14—H14	120.1	N2—C31—H31C	109.5
C13—C14—H14	120.1	H31A—C31—H31C	109.5
C14—C15—C16	120.9 (2)	H31B—C31—H31C	109.5
C14—C15—H15	119.6	N2—C32—C17	107.30 (16)
C16—C15—H15	119.6	N2—C32—S2	126.91 (14)
C11—C16—C15	119.9 (3)	C17—C32—S2	125.76 (15)
C11—C16—H16	120	C2—N1—C9	108.28 (13)
C15—C16—H16	120	C2—N1—C1	126.16 (15)
C25—C17—C32	102.51 (14)	C9—N1—C1	125.56 (16)
C25—C17—C10	116.37 (13)	C32—N2—C30	112.19 (14)
C32—C17—C10	108.64 (13)	C32—N2—C31	124.4 (2)
C25—C17—C18	112.96 (13)	C30—N2—C31	123.4 (2)
C32—C17—C18	106.41 (12)	C9—S1—C10	98.33 (7)
N1—C2—C3—C4	177.99 (18)	C24—C19—C20—C21	−0.5 (3)
C7—C2—C3—C4	−2.2 (3)	C18—C19—C20—C21	177.13 (17)
C2—C3—C4—C5	0.9 (3)	C19—C20—C21—C22	0.1 (3)
C3—C4—C5—C6	0.7 (3)	C20—C21—C22—C23	0.6 (4)
C4—C5—C6—C7	−1.0 (3)	C21—C22—C23—C24	−0.9 (4)
C5—C6—C7—C2	−0.3 (2)	C22—C23—C24—C19	0.5 (3)
C5—C6—C7—C8	−178.61 (18)	C20—C19—C24—C23	0.1 (3)
N1—C2—C7—C6	−178.20 (14)	C18—C19—C24—C23	−177.51 (18)
C3—C2—C7—C6	2.0 (2)	C32—C17—C25—C30	−4.10 (16)
N1—C2—C7—C8	0.53 (18)	C10—C17—C25—C30	−122.49 (15)
C3—C2—C7—C8	−179.30 (16)	C18—C17—C25—C30	110.00 (15)
C6—C7—C8—C9	177.57 (18)	C32—C17—C25—C26	175.90 (17)
C2—C7—C8—C9	−0.87 (18)	C10—C17—C25—C26	57.5 (2)
C6—C7—C8—C18	3.1 (3)	C18—C17—C25—C26	−70.0 (2)
C2—C7—C8—C18	−175.29 (15)	C30—C25—C26—C27	0.9 (3)
C7—C8—C9—N1	0.90 (18)	C17—C25—C26—C27	−179.12 (17)
C18—C8—C9—N1	175.58 (14)	C25—C26—C27—C28	−2.1 (3)
C7—C8—C9—S1	−178.01 (13)	C26—C27—C28—C29	1.1 (3)
C18—C8—C9—S1	−3.3 (3)	C27—C28—C29—C30	1.1 (3)
C17—C10—C11—C16	127.30 (17)	C26—C25—C30—C29	1.3 (3)
S1—C10—C11—C16	−105.96 (16)	C17—C25—C30—C29	−178.66 (17)
C17—C10—C11—C12	−55.1 (2)	C26—C25—C30—N2	−177.65 (15)
S1—C10—C11—C12	71.6 (2)	C17—C25—C30—N2	2.36 (19)
C16—C11—C12—C13	−0.8 (3)	C28—C29—C30—C25	−2.3 (3)
C10—C11—C12—C13	−178.37 (19)	C28—C29—C30—N2	176.4 (2)
C11—C12—C13—C14	1.0 (4)	C25—C17—C32—N2	4.48 (17)
C12—C13—C14—C15	−0.7 (4)	C10—C17—C32—N2	128.19 (15)
C13—C14—C15—C16	0.2 (4)	C18—C17—C32—N2	−114.34 (15)
C12—C11—C16—C15	0.3 (3)	C25—C17—C32—S2	−177.20 (13)
C10—C11—C16—C15	178.02 (18)	C10—C17—C32—S2	−53.50 (19)
C14—C15—C16—C11	0.0 (3)	C18—C17—C32—S2	63.98 (17)
C11—C10—C17—C25	62.35 (19)	C3—C2—N1—C9	179.83 (17)
S1—C10—C17—C25	−60.70 (17)	C7—C2—N1—C9	0.01 (18)
C11—C10—C17—C32	−52.64 (19)	C3—C2—N1—C1	−0.6 (3)
S1—C10—C17—C32	−175.68 (12)	C7—C2—N1—C1	179.58 (16)
C11—C10—C17—C18	−168.32 (14)	C8—C9—N1—C2	−0.59 (19)
S1—C10—C17—C18	68.64 (14)	S1—C9—N1—C2	178.41 (12)
C9—C8—C18—C19	151.50 (15)	C8—C9—N1—C1	179.84 (16)
C7—C8—C18—C19	−35.1 (2)	S1—C9—N1—C1	−1.2 (2)
C9—C8—C18—C17	23.4 (2)	C17—C32—N2—C30	−3.4 (2)
C7—C8—C18—C17	−163.19 (15)	S2—C32—N2—C30	178.31 (13)
C25—C17—C18—C8	76.02 (16)	C17—C32—N2—C31	174.9 (2)
C32—C17—C18—C8	−172.25 (13)	S2—C32—N2—C31	−3.4 (3)
C10—C17—C18—C8	−55.15 (16)	C25—C30—N2—C32	0.7 (2)
C25—C17—C18—C19	−52.46 (17)	C29—C30—N2—C32	−178.17 (19)
C32—C17—C18—C19	59.26 (17)	C25—C30—N2—C31	−177.6 (2)
C10—C17—C18—C19	176.36 (13)	C29—C30—N2—C31	3.5 (3)
C8—C18—C19—C24	132.04 (16)	C8—C9—S1—C10	11.79 (17)
C17—C18—C19—C24	−100.33 (18)	N1—C9—S1—C10	−167.01 (14)
C8—C18—C19—C20	−45.5 (2)	C11—C10—S1—C9	−172.11 (12)
C17—C18—C19—C20	82.11 (19)	C17—C10—S1—C9	−43.28 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···S1	0.96	2.69	3.139 (2)	109
C10—H10···S2	0.98	2.95	3.251 (2)	99
C18—H18···S2	0.98	2.89	3.309 (2)	107
C26—H26···S1	0.93	2.82	3.348 (2)	117
C31—H31C···S2	0.96	2.70	3.169 (4)	111