2-Methyl-1-phenyl­sulfonyl-1H-indole-3-carbonitrile

The title compound, C₁₆H₁₂N₂O₂S, crystallizes with two almost identical mol­ecules in the asymmetric unit. The phenyl ring makes dihedral angles with the mean plane of the indole system of 71.15 (13) and 75.43 (12)°. The mol­ecular structure is stabilized by C—H...O and C—H...N inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.057
• wR factor = 0.184
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.98 Deg.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) .....         10 Ang.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12B   -   C17B    ..       6.02 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C12B
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C8A    -   C10A   ...       1.42 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C8B    -   C10B   ...       1.43 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

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

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

2-Methyl-1-phenylsulfonyl-1H-indole-3-carbonitrile

Crystal data

C16H12N2O2S	Z = 4
Mr = 296.35	F(000) = 616
Triclinic, P1	Dx = 1.405 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7344 (1) Å	Cell parameters from 25 reflections
b = 12.3295 (1) Å	θ = 15–20°
c = 13.3352 (2) Å	µ = 0.24 mm^−1
α = 102.629 (2)°	T = 293 K
β = 97.849 (1)°	Block, colourless
γ = 112.325 (2)°	0.32 × 0.28 × 0.18 mm
V = 1401.30 (4) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	2439 reflections with I > 2σ(I)
Radiation source: fine focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
Nonprofiled ω/2θ scans	h = −1→11
Absorption correction: ψ scan (North et al., 1968)	k = −14→13
Tmin = 0.928, Tmax = 0.959	l = −15→15
5861 measured reflections	3 standard reflections every 100 reflections
4917 independent reflections	intensity decay: 2%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.184	w = 1/[σ^2(Fo^2) + (0.1003P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1	(Δ/σ)max < 0.001
4917 reflections	Δρmax = 0.52 e Å^−3
381 parameters	Δρmin = −0.29 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	Uiso*/Ueq
S1A	0.76301 (14)	0.10871 (10)	0.37440 (10)	0.0536 (4)
O1A	0.8557 (4)	0.0583 (3)	0.4192 (3)	0.0706 (14)
O2A	0.6637 (4)	0.0469 (3)	0.2714 (2)	0.0672 (12)
N1A	0.8866 (4)	0.2454 (3)	0.3688 (3)	0.0466 (12)
N2A	1.0130 (5)	0.5858 (4)	0.2315 (4)	0.0823 (17)
C2A	1.0324 (5)	0.3200 (4)	0.4391 (3)	0.0482 (16)
C3A	1.1116 (5)	0.3004 (5)	0.5240 (4)	0.0631 (17)
C4A	1.2538 (6)	0.3910 (5)	0.5769 (4)	0.0656 (19)
C5A	1.3184 (5)	0.4983 (5)	0.5497 (4)	0.0667 (19)
C6A	1.2397 (5)	0.5178 (4)	0.4667 (4)	0.0603 (17)
C7A	1.0939 (5)	0.4279 (4)	0.4114 (3)	0.0471 (16)
C8A	0.9830 (5)	0.4202 (4)	0.3254 (3)	0.0492 (17)
C9A	0.8571 (5)	0.3102 (4)	0.3002 (3)	0.0483 (17)
C10A	0.9970 (6)	0.5119 (5)	0.2735 (4)	0.0623 (17)
C11A	0.7141 (5)	0.2683 (5)	0.2173 (4)	0.0664 (19)
C12A	0.6582 (5)	0.1445 (4)	0.4639 (3)	0.0465 (16)
C13A	0.7111 (6)	0.1621 (4)	0.5696 (4)	0.0584 (17)
C14A	0.6261 (8)	0.1872 (4)	0.6388 (4)	0.071 (2)
C15A	0.4923 (7)	0.1919 (4)	0.6013 (4)	0.067 (2)
C16A	0.4410 (6)	0.1754 (5)	0.4957 (4)	0.0674 (19)
C17A	0.5223 (5)	0.1487 (4)	0.4263 (4)	0.0542 (17)
S1B	0.65669 (14)	0.77085 (10)	0.11227 (11)	0.0562 (4)
O1B	0.6880 (4)	0.7532 (3)	0.2137 (3)	0.0748 (14)
O2B	0.5200 (3)	0.7808 (3)	0.0742 (3)	0.0803 (16)
N1B	0.8000 (4)	0.9042 (3)	0.1172 (3)	0.0441 (11)
N2B	1.2981 (5)	1.2233 (4)	0.2714 (4)	0.0815 (17)
C2B	0.7879 (5)	0.9832 (4)	0.0560 (3)	0.0425 (14)
C3B	0.6709 (5)	0.9709 (4)	−0.0221 (4)	0.0546 (17)
C4B	0.6955 (6)	1.0649 (5)	−0.0668 (4)	0.0584 (17)
C5B	0.8332 (5)	1.1691 (4)	−0.0350 (4)	0.0560 (17)
C6B	0.9508 (5)	1.1828 (4)	0.0437 (3)	0.0514 (17)
C7B	0.9284 (5)	1.0861 (4)	0.0885 (3)	0.0421 (14)
C8B	1.0232 (5)	1.0701 (4)	0.1708 (3)	0.0450 (16)
C9B	0.9471 (5)	0.9598 (4)	0.1860 (3)	0.0453 (17)
C10B	1.1761 (6)	1.1556 (4)	0.2277 (4)	0.0550 (17)
C11B	1.0060 (6)	0.9064 (4)	0.2615 (4)	0.0645 (19)
C12B	0.6762 (5)	0.6583 (4)	0.0173 (4)	0.0459 (14)
C13B	0.7520 (6)	0.5942 (4)	0.0496 (4)	0.0613 (17)
C14B	0.7669 (7)	0.5057 (5)	−0.0251 (6)	0.080 (2)
C15B	0.7064 (7)	0.4811 (5)	−0.1301 (5)	0.084 (2)
C16B	0.6297 (7)	0.5451 (5)	−0.1620 (5)	0.082 (2)
C17B	0.6132 (6)	0.6348 (4)	−0.0883 (4)	0.0679 (19)
H3A	1.06954	0.22910	0.54354	0.0753*
H4A	1.30910	0.38006	0.63340	0.0788*
H5A	1.41543	0.55738	0.58770	0.0803*
H6A	1.28279	0.58953	0.44787	0.0724*
H11D	0.72131	0.33157	0.18453	0.1003*
H11E	0.62845	0.25071	0.24916	0.1003*
H11F	0.70018	0.19546	0.16481	0.1003*
H13A	0.80201	0.15713	0.59410	0.0703*
H14A	0.66059	0.20082	0.71095	0.0846*
H15A	0.43433	0.20662	0.64814	0.0807*
H16A	0.35130	0.18232	0.47161	0.0807*
H17A	0.48604	0.13346	0.35406	0.0652*
H3B	0.57825	0.90139	−0.04401	0.0659*
H4B	0.61762	1.05855	−0.11981	0.0703*
H5B	0.84612	1.23056	−0.06753	0.0675*
H6B	1.04198	1.25366	0.06659	0.0614*
H11A	1.11357	0.95593	0.29124	0.0971*
H11B	0.98964	0.82459	0.22497	0.0971*
H11C	0.95296	0.90404	0.31716	0.0971*
H13B	0.79296	0.61008	0.12120	0.0735*
H14B	0.81912	0.46203	−0.00367	0.0968*
H15B	0.71726	0.42104	−0.17994	0.1003*
H16B	0.58822	0.52816	−0.23376	0.0980*
H17B	0.56070	0.67824	−0.10976	0.0811*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0529 (7)	0.0403 (6)	0.0610 (8)	0.0155 (6)	0.0193 (6)	0.0069 (5)
O1A	0.069 (2)	0.050 (2)	0.104 (3)	0.0333 (18)	0.028 (2)	0.0249 (19)
O2A	0.068 (2)	0.055 (2)	0.053 (2)	0.0131 (18)	0.0150 (17)	−0.0096 (15)
N1A	0.043 (2)	0.045 (2)	0.048 (2)	0.0178 (18)	0.0101 (18)	0.0088 (18)
N2A	0.081 (3)	0.084 (3)	0.089 (3)	0.034 (3)	0.012 (3)	0.046 (3)
C2A	0.040 (2)	0.048 (3)	0.060 (3)	0.020 (2)	0.015 (2)	0.018 (2)
C3A	0.055 (3)	0.060 (3)	0.074 (3)	0.020 (3)	0.010 (3)	0.031 (3)
C4A	0.060 (3)	0.071 (4)	0.064 (3)	0.031 (3)	0.005 (3)	0.017 (3)
C5A	0.044 (3)	0.064 (3)	0.079 (4)	0.015 (3)	0.000 (3)	0.020 (3)
C6A	0.050 (3)	0.051 (3)	0.075 (3)	0.017 (2)	0.014 (3)	0.018 (3)
C7A	0.047 (3)	0.041 (2)	0.054 (3)	0.021 (2)	0.017 (2)	0.008 (2)
C8A	0.046 (3)	0.053 (3)	0.051 (3)	0.022 (2)	0.010 (2)	0.019 (2)
C9A	0.046 (3)	0.054 (3)	0.042 (3)	0.022 (2)	0.013 (2)	0.006 (2)
C10A	0.059 (3)	0.069 (3)	0.060 (3)	0.027 (3)	0.012 (3)	0.023 (3)
C11A	0.052 (3)	0.083 (4)	0.058 (3)	0.026 (3)	0.003 (3)	0.020 (3)
C12A	0.049 (3)	0.035 (2)	0.052 (3)	0.014 (2)	0.017 (2)	0.010 (2)
C13A	0.074 (3)	0.050 (3)	0.048 (3)	0.025 (3)	0.008 (3)	0.015 (2)
C14A	0.114 (5)	0.051 (3)	0.039 (3)	0.027 (3)	0.024 (3)	0.010 (2)
C15A	0.087 (4)	0.047 (3)	0.072 (4)	0.025 (3)	0.047 (3)	0.017 (3)
C16A	0.061 (3)	0.067 (3)	0.076 (4)	0.028 (3)	0.025 (3)	0.018 (3)
C17A	0.049 (3)	0.057 (3)	0.049 (3)	0.017 (2)	0.017 (2)	0.008 (2)
S1B	0.0541 (7)	0.0424 (7)	0.0780 (9)	0.0196 (6)	0.0332 (7)	0.0202 (6)
O1B	0.102 (3)	0.063 (2)	0.067 (2)	0.028 (2)	0.047 (2)	0.0301 (18)
O2B	0.046 (2)	0.053 (2)	0.144 (4)	0.0194 (17)	0.033 (2)	0.030 (2)
N1B	0.042 (2)	0.0385 (19)	0.053 (2)	0.0176 (17)	0.0155 (17)	0.0122 (17)
N2B	0.062 (3)	0.078 (3)	0.081 (3)	0.012 (3)	−0.007 (3)	0.026 (3)
C2B	0.045 (2)	0.035 (2)	0.046 (3)	0.017 (2)	0.014 (2)	0.0071 (19)
C3B	0.041 (3)	0.049 (3)	0.066 (3)	0.017 (2)	0.006 (2)	0.010 (2)
C4B	0.059 (3)	0.068 (3)	0.052 (3)	0.040 (3)	−0.001 (2)	0.010 (3)
C5B	0.065 (3)	0.058 (3)	0.054 (3)	0.030 (3)	0.017 (3)	0.025 (2)
C6B	0.049 (3)	0.048 (3)	0.057 (3)	0.018 (2)	0.011 (2)	0.021 (2)
C7B	0.046 (3)	0.040 (2)	0.040 (2)	0.018 (2)	0.016 (2)	0.0081 (19)
C8B	0.041 (2)	0.046 (3)	0.047 (3)	0.018 (2)	0.012 (2)	0.012 (2)
C9B	0.053 (3)	0.046 (3)	0.044 (3)	0.027 (2)	0.018 (2)	0.012 (2)
C10B	0.057 (3)	0.059 (3)	0.047 (3)	0.023 (3)	0.009 (2)	0.017 (2)
C11B	0.082 (4)	0.068 (3)	0.061 (3)	0.044 (3)	0.019 (3)	0.029 (3)
C12B	0.044 (2)	0.039 (2)	0.053 (3)	0.014 (2)	0.015 (2)	0.015 (2)
C13B	0.071 (3)	0.048 (3)	0.069 (3)	0.029 (3)	0.016 (3)	0.019 (3)
C14B	0.082 (4)	0.050 (3)	0.111 (5)	0.032 (3)	0.031 (4)	0.015 (3)
C15B	0.086 (4)	0.042 (3)	0.095 (5)	0.009 (3)	0.041 (4)	−0.013 (3)
C16B	0.079 (4)	0.060 (4)	0.079 (4)	0.011 (3)	0.016 (3)	0.005 (3)
C17B	0.058 (3)	0.051 (3)	0.085 (4)	0.017 (3)	0.006 (3)	0.020 (3)

Geometric parameters (Å, º)

S1A—O1A	1.414 (4)	C11A—H11E	0.9600
S1A—O2A	1.422 (3)	C11A—H11F	0.9600
S1A—N1A	1.683 (4)	C13A—H13A	0.9300
S1A—C12A	1.762 (5)	C14A—H14A	0.9300
S1B—O1B	1.427 (4)	C15A—H15A	0.9300
S1B—O2B	1.418 (4)	C16A—H16A	0.9300
S1B—N1B	1.685 (4)	C17A—H17A	0.9300
S1B—C12B	1.750 (5)	C2B—C3B	1.371 (7)
N1A—C9A	1.407 (6)	C2B—C7B	1.396 (7)
N1A—C2A	1.417 (6)	C3B—C4B	1.373 (8)
N2A—C10A	1.143 (8)	C4B—C5B	1.388 (8)
N1B—C9B	1.408 (6)	C5B—C6B	1.374 (7)
N1B—C2B	1.427 (6)	C6B—C7B	1.406 (6)
N2B—C10B	1.137 (8)	C7B—C8B	1.432 (6)
C2A—C7A	1.391 (7)	C8B—C9B	1.355 (7)
C2A—C3A	1.399 (7)	C8B—C10B	1.433 (7)
C3A—C4A	1.370 (8)	C9B—C11B	1.482 (7)
C4A—C5A	1.385 (8)	C12B—C13B	1.364 (8)
C5A—C6A	1.376 (7)	C12B—C17B	1.376 (7)
C6A—C7A	1.396 (7)	C13B—C14B	1.374 (9)
C7A—C8A	1.423 (6)	C14B—C15B	1.361 (10)
C8A—C9A	1.371 (7)	C15B—C16B	1.367 (10)
C8A—C10A	1.424 (7)	C16B—C17B	1.385 (8)
C9A—C11A	1.487 (7)	C3B—H3B	0.9300
C12A—C13A	1.372 (6)	C4B—H4B	0.9300
C12A—C17A	1.374 (7)	C5B—H5B	0.9300
C13A—C14A	1.382 (9)	C6B—H6B	0.9300
C14A—C15A	1.357 (10)	C11B—H11A	0.9600
C15A—C16A	1.371 (7)	C11B—H11B	0.9600
C16A—C17A	1.362 (8)	C11B—H11C	0.9600
C3A—H3A	0.9300	C13B—H13B	0.9300
C4A—H4A	0.9300	C14B—H14B	0.9300
C5A—H5A	0.9300	C15B—H15B	0.9300
C6A—H6A	0.9300	C16B—H16B	0.9300
C11A—H11D	0.9600	C17B—H17B	0.9300
S1A···H3A	3.0900	C14A···H15B^xi	3.0600
S1A···H11E	3.1600	C14A···H6A^iv	3.0800
S1B···H3B	3.0800	C14B···H6B^vii	3.0600
S1B···H11B	3.1300	C15A···H6A^iv	3.0300
O1A···C3A	2.940 (7)	C15B···H6B^vii	3.0900
O1A···C11B^i	3.357 (7)	C16A···H6A^iv	2.9600
O1B···C11B	2.837 (7)	C16B···H6B^vii	3.0800
O1B···C15A^ii	3.314 (7)	C17A···H11E	3.0300
O2A···C2B^i	3.319 (5)	C17A···H6A^iv	2.9900
O2A···N1B^i	3.166 (5)	C17B···H6B^vii	3.0500
O2A···C11A	2.855 (7)	H3A···S1A	3.0900
O2B···C4B^iii	3.330 (7)	H3A···O1A	2.3900
O2B···C3B	2.918 (6)	H3B···S1B	3.0800
O1A···H13A	2.6000	H3B···C11A^v	3.0600
O1A···H11C^i	2.6400	H3B···O2B	2.3800
O1A···H3A	2.3900	H4A···O1B^iv	2.8900
O1B···H11C	2.5100	H4B···O2B^iii	2.7900
O1B···H4A^iv	2.8900	H4B···O2A^v	2.8100
O1B···H15A^ii	2.3900	H6A···C16A^iv	2.9600
O1B···H11B	2.7000	H6A···C17A^iv	2.9900
O1B···H13B	2.5400	H6A···C15A^iv	3.0300
O2A···H17A	2.6000	H6A···C10A	3.0500
O2A···H4B^v	2.8100	H6A···C12A^iv	3.0300
O2A···H11F	2.5100	H6A···C14A^iv	3.0800
O2A···H11E	2.7300	H6B···C10B	3.0600
O2B···H3B	2.3800	H6B···C14B^vii	3.0600
O2B···H4B^iii	2.7900	H6B···C15B^vii	3.0900
O2B···H17B	2.6600	H6B···C16B^vii	3.0800
N1B···O2A^vi	3.166 (5)	H6B···C17B^vii	3.0500
N2A···C13B	3.313 (8)	H6B···C12B^vii	3.0100
N2B···C17B^vii	3.326 (7)	H6B···C13B^vii	3.0300
N2B···C17A^viii	3.317 (7)	H11A···C10B	2.6600
N2B···C16A^viii	3.390 (7)	H11A···H13A^iv	2.5300
N2B···C16B^vii	3.369 (8)	H11B···O1B	2.7000
N2A···H13B	2.5800	H11B···S1B	3.1300
N2A···H15B^ix	2.8300	H11B···H13B	2.5300
N2B···H17B^vii	2.9500	H11B···C13B	3.0800
N2B···H17A^viii	2.7000	H11C···O1B	2.5100
N2B···H16A^viii	2.8400	H11C···O1A^vi	2.6400
C2B···O2A^vi	3.319 (5)	H11D···C10A	2.6500
C3A···O1A	2.940 (7)	H11E···O2A	2.7300
C3B···O2B	2.918 (6)	H11E···C17A	3.0300
C4B···O2B^iii	3.330 (7)	H11E···H17A	2.4200
C11A···O2A	2.855 (7)	H11E···S1A	3.1600
C11B···O1B	2.837 (7)	H11F···O2A	2.5100
C11B···O1A^vi	3.357 (7)	H13A···O1A	2.6000
C13B···N2A	3.313 (8)	H13A···C11B^iv	2.9300
C15A···O1B^ii	3.314 (7)	H13A···H11A^iv	2.5300
C16A···N2B^x	3.390 (7)	H13B···N2A	2.5800
C16B···N2B^vii	3.369 (8)	H13B···H11B	2.5300
C17A···N2B^x	3.317 (7)	H13B···O1B	2.5400
C17B···N2B^vii	3.326 (7)	H14A···H15B^xi	2.5900
C10A···H11D	2.6500	H15A···O1B^ii	2.3900
C10A···H6A	3.0500	H15B···N2A^ix	2.8300
C10B···H11A	2.6600	H15B···C14A^xii	3.0600
C10B···H6B	3.0600	H15B···H14A^xii	2.5900
C11A···H3B^v	3.0600	H16A···N2B^x	2.8400
C11B···H13A^iv	2.9300	H17A···O2A	2.6000
C12A···H6A^iv	3.0300	H17A···N2B^x	2.7000
C12B···H6B^vii	3.0100	H17A···H11E	2.4200
C13B···H11B	3.0800	H17B···O2B	2.6600
C13B···H6B^vii	3.0300	H17B···N2B^vii	2.9500
O1A—S1A—O2A	120.7 (2)	C14A—C13A—H13A	121.00
O1A—S1A—N1A	105.1 (2)	C15A—C14A—H14A	120.00
O1A—S1A—C12A	109.5 (2)	C13A—C14A—H14A	120.00
O2A—S1A—N1A	106.2 (2)	C16A—C15A—H15A	119.00
O2A—S1A—C12A	109.2 (2)	C14A—C15A—H15A	119.00
N1A—S1A—C12A	104.9 (2)	C15A—C16A—H16A	120.00
O1B—S1B—N1B	106.0 (2)	C17A—C16A—H16A	120.00
O1B—S1B—C12B	108.9 (2)	C16A—C17A—H17A	120.00
O2B—S1B—N1B	105.4 (2)	C12A—C17A—H17A	120.00
O2B—S1B—C12B	109.5 (2)	N1B—C2B—C3B	131.7 (4)
N1B—S1B—C12B	105.1 (2)	N1B—C2B—C7B	106.5 (4)
O1B—S1B—O2B	120.8 (2)	C3B—C2B—C7B	121.8 (4)
S1A—N1A—C9A	125.8 (3)	C2B—C3B—C4B	117.6 (5)
S1A—N1A—C2A	125.6 (3)	C3B—C4B—C5B	121.8 (5)
C2A—N1A—C9A	108.3 (4)	C4B—C5B—C6B	121.0 (5)
S1B—N1B—C2B	124.9 (3)	C5B—C6B—C7B	117.7 (4)
S1B—N1B—C9B	126.2 (3)	C2B—C7B—C6B	119.9 (4)
C2B—N1B—C9B	108.8 (4)	C2B—C7B—C8B	107.5 (4)
C3A—C2A—C7A	121.5 (5)	C6B—C7B—C8B	132.5 (4)
N1A—C2A—C3A	130.9 (4)	C7B—C8B—C9B	109.5 (4)
N1A—C2A—C7A	107.6 (4)	C7B—C8B—C10B	125.8 (4)
C2A—C3A—C4A	117.0 (5)	C9B—C8B—C10B	124.6 (4)
C3A—C4A—C5A	122.6 (5)	N1B—C9B—C8B	107.7 (4)
C4A—C5A—C6A	120.3 (5)	N1B—C9B—C11B	125.6 (4)
C5A—C6A—C7A	118.7 (5)	C8B—C9B—C11B	126.7 (4)
C2A—C7A—C8A	107.1 (4)	N2B—C10B—C8B	178.9 (5)
C6A—C7A—C8A	132.9 (4)	S1B—C12B—C13B	119.2 (4)
C2A—C7A—C6A	119.9 (4)	S1B—C12B—C17B	119.6 (4)
C9A—C8A—C10A	124.4 (4)	C13B—C12B—C17B	121.2 (5)
C7A—C8A—C10A	126.2 (5)	C12B—C13B—C14B	119.1 (5)
C7A—C8A—C9A	109.4 (4)	C13B—C14B—C15B	120.9 (6)
N1A—C9A—C11A	126.3 (4)	C14B—C15B—C16B	119.7 (6)
N1A—C9A—C8A	107.5 (4)	C15B—C16B—C17B	120.5 (6)
C8A—C9A—C11A	126.3 (4)	C12B—C17B—C16B	118.6 (5)
N2A—C10A—C8A	177.7 (7)	C2B—C3B—H3B	121.00
S1A—C12A—C13A	119.0 (4)	C4B—C3B—H3B	121.00
S1A—C12A—C17A	119.6 (3)	C3B—C4B—H4B	119.00
C13A—C12A—C17A	121.3 (5)	C5B—C4B—H4B	119.00
C12A—C13A—C14A	118.5 (5)	C4B—C5B—H5B	119.00
C13A—C14A—C15A	119.9 (5)	C6B—C5B—H5B	119.00
C14A—C15A—C16A	121.2 (6)	C5B—C6B—H6B	121.00
C15A—C16A—C17A	119.5 (6)	C7B—C6B—H6B	121.00
C12A—C17A—C16A	119.4 (5)	C9B—C11B—H11A	109.00
C4A—C3A—H3A	122.00	C9B—C11B—H11B	109.00
C2A—C3A—H3A	121.00	C9B—C11B—H11C	109.00
C3A—C4A—H4A	119.00	H11A—C11B—H11B	109.00
C5A—C4A—H4A	119.00	H11A—C11B—H11C	109.00
C6A—C5A—H5A	120.00	H11B—C11B—H11C	109.00
C4A—C5A—H5A	120.00	C12B—C13B—H13B	120.00
C5A—C6A—H6A	121.00	C14B—C13B—H13B	120.00
C7A—C6A—H6A	121.00	C13B—C14B—H14B	120.00
C9A—C11A—H11D	109.00	C15B—C14B—H14B	120.00
C9A—C11A—H11F	109.00	C14B—C15B—H15B	120.00
H11D—C11A—H11E	109.00	C16B—C15B—H15B	120.00
H11D—C11A—H11F	110.00	C15B—C16B—H16B	120.00
H11E—C11A—H11F	109.00	C17B—C16B—H16B	120.00
C9A—C11A—H11E	109.00	C12B—C17B—H17B	121.00
C12A—C13A—H13A	121.00	C16B—C17B—H17B	121.00
O1A—S1A—N1A—C2A	−29.5 (4)	C3A—C4A—C5A—C6A	0.1 (9)
O1A—S1A—N1A—C9A	157.0 (4)	C4A—C5A—C6A—C7A	0.4 (8)
O2A—S1A—N1A—C2A	−158.4 (4)	C5A—C6A—C7A—C8A	178.4 (5)
O2A—S1A—N1A—C9A	28.0 (4)	C5A—C6A—C7A—C2A	−1.4 (7)
C12A—S1A—N1A—C2A	86.0 (4)	C6A—C7A—C8A—C9A	179.7 (5)
C12A—S1A—N1A—C9A	−87.6 (4)	C2A—C7A—C8A—C9A	−0.5 (5)
O1A—S1A—C12A—C13A	22.2 (5)	C2A—C7A—C8A—C10A	178.6 (5)
O1A—S1A—C12A—C17A	−154.8 (4)	C6A—C7A—C8A—C10A	−1.3 (9)
O2A—S1A—C12A—C13A	156.4 (4)	C10A—C8A—C9A—C11A	−1.2 (8)
O2A—S1A—C12A—C17A	−20.7 (5)	C10A—C8A—C9A—N1A	−179.9 (5)
N1A—S1A—C12A—C13A	−90.1 (4)	C7A—C8A—C9A—N1A	−0.8 (5)
N1A—S1A—C12A—C17A	92.8 (4)	C7A—C8A—C9A—C11A	177.9 (5)
N1B—S1B—C12B—C17B	−84.3 (5)	S1A—C12A—C17A—C16A	179.5 (4)
C12B—S1B—N1B—C2B	92.2 (4)	C13A—C12A—C17A—C16A	2.5 (8)
C12B—S1B—N1B—C9B	−91.9 (4)	C17A—C12A—C13A—C14A	−1.5 (7)
O1B—S1B—C12B—C13B	−16.6 (5)	S1A—C12A—C13A—C14A	−178.5 (4)
O1B—S1B—N1B—C2B	−152.5 (4)	C12A—C13A—C14A—C15A	1.1 (7)
O1B—S1B—N1B—C9B	23.3 (5)	C13A—C14A—C15A—C16A	−1.8 (8)
O2B—S1B—N1B—C2B	−23.4 (4)	C14A—C15A—C16A—C17A	2.8 (8)
O2B—S1B—N1B—C9B	152.5 (4)	C15A—C16A—C17A—C12A	−3.1 (8)
O1B—S1B—C12B—C17B	162.5 (4)	C7B—C2B—C3B—C4B	−1.0 (7)
O2B—S1B—C12B—C13B	−150.6 (4)	N1B—C2B—C7B—C6B	−178.6 (4)
O2B—S1B—C12B—C17B	28.5 (5)	N1B—C2B—C7B—C8B	−1.4 (5)
N1B—S1B—C12B—C13B	96.6 (4)	N1B—C2B—C3B—C4B	−179.7 (5)
S1A—N1A—C2A—C7A	−176.5 (3)	C3B—C2B—C7B—C6B	2.5 (7)
C9A—N1A—C2A—C7A	−2.0 (5)	C3B—C2B—C7B—C8B	179.6 (4)
C9A—N1A—C2A—C3A	177.3 (5)	C2B—C3B—C4B—C5B	0.1 (8)
S1A—N1A—C2A—C3A	2.8 (8)	C3B—C4B—C5B—C6B	−0.5 (8)
S1A—N1A—C9A—C8A	176.2 (3)	C4B—C5B—C6B—C7B	1.9 (7)
C2A—N1A—C9A—C8A	1.7 (5)	C5B—C6B—C7B—C8B	−179.2 (5)
S1A—N1A—C9A—C11A	−2.5 (7)	C5B—C6B—C7B—C2B	−2.8 (7)
C2A—N1A—C9A—C11A	−177.0 (4)	C2B—C7B—C8B—C9B	2.3 (5)
C2B—N1B—C9B—C11B	−179.0 (4)	C2B—C7B—C8B—C10B	−178.8 (5)
C9B—N1B—C2B—C3B	178.9 (5)	C6B—C7B—C8B—C9B	179.0 (5)
S1B—N1B—C2B—C7B	176.5 (3)	C6B—C7B—C8B—C10B	−2.1 (9)
S1B—N1B—C2B—C3B	−4.7 (7)	C7B—C8B—C9B—C11B	178.1 (5)
S1B—N1B—C9B—C11B	4.6 (7)	C10B—C8B—C9B—N1B	178.8 (5)
S1B—N1B—C9B—C8B	−175.0 (3)	C10B—C8B—C9B—C11B	−0.8 (8)
C9B—N1B—C2B—C7B	0.1 (5)	C7B—C8B—C9B—N1B	−2.2 (5)
C2B—N1B—C9B—C8B	1.4 (5)	S1B—C12B—C13B—C14B	179.9 (5)
C7A—C2A—C3A—C4A	−1.5 (8)	C17B—C12B—C13B—C14B	0.8 (8)
N1A—C2A—C7A—C6A	−178.6 (4)	S1B—C12B—C17B—C16B	−179.8 (4)
N1A—C2A—C3A—C4A	179.3 (5)	C13B—C12B—C17B—C16B	−0.7 (8)
C3A—C2A—C7A—C6A	2.0 (7)	C12B—C13B—C14B—C15B	−0.4 (9)
N1A—C2A—C7A—C8A	1.5 (5)	C13B—C14B—C15B—C16B	0.0 (10)
C3A—C2A—C7A—C8A	−177.9 (5)	C14B—C15B—C16B—C17B	0.0 (10)
C2A—C3A—C4A—C5A	0.4 (8)	C15B—C16B—C17B—C12B	0.3 (9)

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z; (iv) −x+2, −y+1, −z+1; (v) −x+1, −y+1, −z; (vi) x, y+1, z; (vii) −x+2, −y+2, −z; (viii) x+1, y+1, z; (ix) −x+2, −y+1, −z; (x) x−1, y−1, z; (xi) x, y, z+1; (xii) x, y, z−1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3A—H3A···O1A	0.9300	2.3900	2.940 (7)	118.00
C3B—H3B···O2B	0.9300	2.3800	2.918 (6)	117.00
C11B—H11C···O1B	0.9600	2.5100	2.837 (7)	100.00
C11A—H11F···O2A	0.9600	2.5100	2.855 (7)	101.00
C13B—H13B···O1B	0.9300	2.5400	2.906 (7)	104.00
C13B—H13B···N2A	0.9300	2.5800	3.313 (8)	136.00
C15A—H15A···O1B^ii	0.9300	2.3900	3.314 (7)	172.00
C17A—H17A···O2A	0.9300	2.6000	2.948 (6)	103.00

Symmetry code: (ii) −x+1, −y+1, −z+1.