N-[(R)-1-Phenyl­ethyl]thio­benzamide

The title compound, C₁₅H₁₅NS, crystallizes with two crystallographically independent and conformationally almost identical mol­ecules in the asymmetric unit. Both mol­ecules are non-planar, the dihedral angle between the two phenyl planes in each mol­ecule being 76.41 (11) and 86.65 (10)°. An anti conformation of the amide and thio groups is observed in the thio­amide fragment. In the solid state, the structure is stabilized by weak C—H...S intra­molecular inter­actions, inter­molecular N—H...S hydrogen bonds and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.117
• Data-to-parameter ratio = 21.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13A   ..  CG2     ..       2.97 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15F   ..  CG3     ..       3.11 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8AA   ..  CG4     ..       2.98 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2BA   ..  CG4     ..       3.13 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         14
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C15 H15 N S

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           29.00
           From the CIF: _reflns_number_total               6772
           Count of symmetry unique reflns         3790
           Completeness (_total/calc)            178.68%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2982
           Fraction of Friedel pairs measured     0.787
           Are heavy atom types Z>Si present        yes

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   7 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

N-[(R)-1-Phenylethyl]thiobenzamide

Crystal data

C15H15NS	Dx = 1.257 Mg m^−3
Mr = 241.35	Melting point = 338–339 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6772 reflections
a = 10.4149 (3) Å	θ = 1.8–29.0°
b = 15.0106 (5) Å	µ = 0.23 mm^−1
c = 16.3110 (5) Å	T = 100 K
V = 2549.96 (14) Å^3	Needle, yellow
Z = 8	0.50 × 0.24 × 0.24 mm
F(000) = 1024

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	6772 independent reflections
Radiation source: fine-focus sealed tube	6150 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
Detector resolution: 8.33 pixels mm^-1	θmax = 29.0°, θmin = 1.8°
ω scans	h = −12→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −20→20
Tmin = 0.936, Tmax = 0.946	l = −22→22
50018 measured reflections

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)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0579P)^2 + 0.9357P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.001
6772 reflections	Δρmax = 0.43 e Å^−3
317 parameters	Δρmin = −0.35 e Å^−3
0 restraints	Absolute structure: Flack (1983), 2982 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (6)

Special details

Experimental. The low-temparture data were collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
S1A	0.50319 (6)	0.44060 (4)	0.97712 (3)	0.02289 (12)
N1A	0.3307 (2)	0.37466 (12)	0.87364 (10)	0.0206 (4)
C1A	0.5838 (2)	0.52140 (16)	0.80813 (14)	0.0249 (5)
H1AA	0.5938	0.5533	0.8566	0.030*
C2A	0.6447 (2)	0.55053 (18)	0.73696 (15)	0.0306 (5)
H2AA	0.6945	0.6019	0.7377	0.037*
C3A	0.6306 (2)	0.50226 (19)	0.66480 (15)	0.0306 (5)
H3AA	0.6713	0.5214	0.6172	0.037*
C4A	0.5568 (2)	0.42658 (17)	0.66348 (13)	0.0261 (5)
H4AA	0.5470	0.3951	0.6148	0.031*
C5A	0.4964 (2)	0.39655 (15)	0.73464 (12)	0.0224 (4)
H5AA	0.4484	0.3443	0.7336	0.027*
C6A	0.5080 (2)	0.44499 (14)	0.80748 (12)	0.0194 (4)
C7A	0.4406 (2)	0.41715 (14)	0.88413 (12)	0.0179 (4)
C8A	0.2408 (2)	0.34686 (15)	0.93850 (12)	0.0222 (4)
H8AA	0.2837	0.3557	0.9913	0.027*
C9A	0.1231 (2)	0.40747 (15)	0.93661 (12)	0.0222 (5)
C10A	−0.0005 (2)	0.37546 (16)	0.95161 (13)	0.0255 (4)
H10A	−0.0129	0.3153	0.9627	0.031*
C11A	−0.1052 (2)	0.43292 (18)	0.95005 (14)	0.0286 (5)
H11A	−0.1872	0.4106	0.9594	0.034*
C12A	−0.0889 (2)	0.52309 (18)	0.93468 (14)	0.0294 (5)
H12A	−0.1591	0.5614	0.9342	0.035*
C13A	0.0342 (2)	0.55537 (17)	0.91992 (15)	0.0298 (5)
H13A	0.0465	0.6157	0.9097	0.036*
C14A	0.1381 (2)	0.49824 (16)	0.92039 (13)	0.0253 (5)
H14A	0.2197	0.5206	0.9097	0.030*
C15A	0.2131 (2)	0.24741 (15)	0.92945 (14)	0.0261 (5)
H15A	0.2926	0.2155	0.9247	0.039*
H15B	0.1621	0.2376	0.8812	0.039*
H15C	0.1671	0.2267	0.9768	0.039*
S1B	1.18146 (6)	0.28211 (4)	0.70624 (3)	0.02361 (13)
N1B	1.16272 (18)	0.43063 (12)	0.61946 (10)	0.0198 (4)
C1B	1.1588 (2)	0.33151 (14)	0.46755 (12)	0.0208 (4)
H1BA	1.0998	0.3779	0.4694	0.025*
C2B	1.1882 (2)	0.29161 (15)	0.39296 (13)	0.0234 (4)
H2BA	1.1489	0.3113	0.3451	0.028*
C3B	1.2763 (2)	0.22240 (16)	0.39018 (13)	0.0252 (5)
H3BA	1.2960	0.1955	0.3404	0.030*
C4B	1.3349 (2)	0.19329 (15)	0.46175 (14)	0.0254 (5)
H4BA	1.3943	0.1471	0.4596	0.031*
C5B	1.3058 (2)	0.23241 (14)	0.53607 (13)	0.0235 (4)
H5BA	1.3451	0.2122	0.5838	0.028*
C6B	1.2174 (2)	0.30230 (14)	0.53970 (12)	0.0188 (4)
C7B	1.1866 (2)	0.34414 (14)	0.62053 (12)	0.0186 (4)
C8B	1.1217 (2)	0.48434 (14)	0.69057 (12)	0.0199 (4)
H8BA	1.1621	0.4586	0.7394	0.024*
C9B	1.1718 (2)	0.57873 (14)	0.68147 (11)	0.0187 (4)
C10B	1.0941 (2)	0.65238 (15)	0.69479 (13)	0.0225 (4)
H10B	1.0088	0.6443	0.7101	0.027*
C11B	1.1424 (3)	0.73789 (16)	0.68549 (13)	0.0272 (5)
H11B	1.0889	0.7867	0.6937	0.033*
C12B	1.2696 (3)	0.75125 (16)	0.66406 (13)	0.0272 (5)
H12B	1.3015	0.8087	0.6578	0.033*
C13B	1.3486 (2)	0.67860 (16)	0.65210 (14)	0.0264 (5)
H13B	1.4343	0.6871	0.6382	0.032*
C14B	1.3005 (2)	0.59282 (15)	0.66078 (13)	0.0225 (4)
H14B	1.3544	0.5442	0.6527	0.027*
C15B	0.9769 (2)	0.47600 (16)	0.70140 (14)	0.0261 (5)
H15D	0.9533	0.4142	0.7014	0.039*
H15E	0.9342	0.5060	0.6571	0.039*
H15F	0.9521	0.5026	0.7525	0.039*
H1NB	1.158 (3)	0.4566 (18)	0.5744 (18)	0.030 (7)*
H1NA	0.304 (3)	0.364 (2)	0.827 (2)	0.048 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0245 (3)	0.0295 (3)	0.0146 (2)	0.0019 (2)	−0.0029 (2)	−0.0031 (2)
N1A	0.0274 (10)	0.0242 (10)	0.0102 (7)	−0.0001 (8)	0.0007 (7)	0.0006 (6)
C1A	0.0265 (12)	0.0270 (12)	0.0211 (10)	0.0005 (9)	0.0011 (9)	0.0010 (9)
C2A	0.0270 (12)	0.0356 (13)	0.0291 (11)	−0.0059 (11)	0.0027 (9)	0.0046 (10)
C3A	0.0251 (12)	0.0443 (15)	0.0224 (11)	0.0052 (11)	0.0068 (9)	0.0092 (10)
C4A	0.0254 (11)	0.0378 (14)	0.0151 (9)	0.0076 (10)	0.0023 (8)	0.0001 (9)
C5A	0.0236 (10)	0.0247 (11)	0.0187 (9)	0.0027 (10)	0.0013 (9)	−0.0011 (8)
C6A	0.0204 (9)	0.0229 (10)	0.0148 (8)	0.0084 (9)	0.0034 (8)	0.0002 (7)
C7A	0.0198 (10)	0.0203 (10)	0.0136 (9)	0.0042 (8)	−0.0015 (7)	−0.0004 (7)
C8A	0.0273 (11)	0.0284 (11)	0.0110 (9)	−0.0025 (9)	0.0013 (8)	0.0021 (8)
C9A	0.0282 (11)	0.0279 (12)	0.0104 (9)	−0.0012 (9)	−0.0015 (8)	−0.0024 (8)
C10A	0.0316 (12)	0.0285 (11)	0.0163 (9)	−0.0060 (10)	0.0021 (10)	0.0008 (8)
C11A	0.0247 (11)	0.0405 (14)	0.0206 (10)	−0.0022 (10)	0.0023 (9)	−0.0011 (10)
C12A	0.0297 (12)	0.0381 (14)	0.0205 (10)	0.0061 (10)	0.0004 (9)	−0.0072 (10)
C13A	0.0378 (13)	0.0247 (12)	0.0270 (11)	−0.0003 (11)	−0.0006 (10)	−0.0044 (9)
C14A	0.0290 (12)	0.0257 (12)	0.0212 (10)	−0.0064 (9)	0.0015 (9)	−0.0034 (9)
C15A	0.0324 (12)	0.0254 (11)	0.0206 (10)	0.0001 (10)	0.0005 (9)	0.0037 (9)
S1B	0.0360 (3)	0.0208 (2)	0.0140 (2)	−0.0022 (2)	−0.0013 (2)	0.00253 (19)
N1B	0.0280 (10)	0.0206 (9)	0.0108 (7)	0.0003 (8)	0.0002 (7)	0.0010 (6)
C1B	0.0254 (11)	0.0207 (10)	0.0161 (9)	0.0025 (9)	0.0006 (8)	−0.0005 (8)
C2B	0.0293 (11)	0.0263 (11)	0.0146 (9)	−0.0017 (10)	−0.0004 (8)	−0.0012 (8)
C3B	0.0300 (12)	0.0268 (11)	0.0188 (10)	−0.0036 (10)	0.0041 (9)	−0.0056 (9)
C4B	0.0271 (12)	0.0233 (11)	0.0259 (11)	0.0047 (9)	0.0029 (9)	−0.0019 (9)
C5B	0.0277 (11)	0.0225 (11)	0.0204 (10)	0.0002 (9)	−0.0019 (8)	−0.0008 (8)
C6B	0.0229 (10)	0.0188 (10)	0.0147 (9)	−0.0030 (8)	0.0010 (7)	−0.0015 (7)
C7B	0.0216 (10)	0.0199 (10)	0.0144 (8)	−0.0020 (9)	−0.0021 (8)	−0.0012 (7)
C8B	0.0269 (11)	0.0204 (10)	0.0124 (9)	−0.0002 (9)	0.0008 (8)	−0.0013 (7)
C9B	0.0248 (11)	0.0206 (10)	0.0108 (8)	−0.0019 (8)	−0.0026 (7)	−0.0002 (7)
C10B	0.0266 (11)	0.0262 (11)	0.0148 (9)	0.0023 (9)	−0.0010 (8)	−0.0033 (8)
C11B	0.0391 (14)	0.0232 (12)	0.0192 (10)	0.0067 (10)	−0.0054 (9)	−0.0035 (8)
C12B	0.0415 (14)	0.0217 (11)	0.0184 (10)	−0.0084 (10)	−0.0059 (9)	0.0005 (8)
C13B	0.0257 (12)	0.0328 (13)	0.0208 (10)	−0.0055 (10)	−0.0019 (9)	0.0002 (9)
C14B	0.0229 (11)	0.0269 (11)	0.0176 (9)	0.0023 (9)	−0.0009 (8)	−0.0007 (8)
C15B	0.0282 (12)	0.0290 (11)	0.0211 (10)	−0.0046 (9)	0.0040 (9)	−0.0032 (9)

Geometric parameters (Å, º)

S1A—C7A	1.688 (2)	S1B—C7B	1.681 (2)
N1A—C7A	1.321 (3)	N1B—C7B	1.322 (3)
N1A—C8A	1.473 (3)	N1B—C8B	1.476 (3)
N1A—H1NA	0.83 (4)	N1B—H1NB	0.83 (3)
C1A—C6A	1.392 (3)	C1B—C2B	1.390 (3)
C1A—C2A	1.393 (3)	C1B—C6B	1.396 (3)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.390 (4)	C2B—C3B	1.386 (3)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.372 (4)	C3B—C4B	1.388 (3)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.395 (3)	C4B—C5B	1.381 (3)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.398 (3)	C5B—C6B	1.397 (3)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.494 (3)	C6B—C7B	1.495 (3)
C8A—C9A	1.527 (3)	C8B—C9B	1.517 (3)
C8A—C15A	1.528 (3)	C8B—C15B	1.523 (3)
C8A—H8AA	0.9800	C8B—H8BA	0.9800
C9A—C10A	1.396 (3)	C9B—C10B	1.387 (3)
C9A—C14A	1.397 (3)	C9B—C14B	1.398 (3)
C10A—C11A	1.391 (4)	C10B—C11B	1.387 (3)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.387 (4)	C11B—C12B	1.384 (4)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.391 (4)	C12B—C13B	1.380 (4)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.381 (4)	C13B—C14B	1.389 (3)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C7A—N1A—C8A	126.46 (18)	C7B—N1B—C8B	125.49 (17)
C7A—N1A—H1NA	120 (2)	C7B—N1B—H1NB	118.7 (19)
C8A—N1A—H1NA	113 (2)	C8B—N1B—H1NB	115.0 (19)
C6A—C1A—C2A	120.7 (2)	C2B—C1B—C6B	120.4 (2)
C6A—C1A—H1AA	119.7	C2B—C1B—H1BA	119.8
C2A—C1A—H1AA	119.7	C6B—C1B—H1BA	119.8
C3A—C2A—C1A	119.6 (2)	C3B—C2B—C1B	119.8 (2)
C3A—C2A—H2AA	120.2	C3B—C2B—H2BA	120.1
C1A—C2A—H2AA	120.2	C1B—C2B—H2BA	120.1
C4A—C3A—C2A	120.3 (2)	C2B—C3B—C4B	120.0 (2)
C4A—C3A—H3AA	119.9	C2B—C3B—H3BA	120.0
C2A—C3A—H3AA	119.9	C4B—C3B—H3BA	120.0
C3A—C4A—C5A	120.5 (2)	C5B—C4B—C3B	120.5 (2)
C3A—C4A—H4AA	119.8	C5B—C4B—H4BA	119.7
C5A—C4A—H4AA	119.8	C3B—C4B—H4BA	119.7
C4A—C5A—C6A	120.0 (2)	C4B—C5B—C6B	120.1 (2)
C4A—C5A—H5AA	120.0	C4B—C5B—H5BA	120.0
C6A—C5A—H5AA	120.0	C6B—C5B—H5BA	120.0
C1A—C6A—C5A	118.9 (2)	C1B—C6B—C5B	119.21 (19)
C1A—C6A—C7A	119.38 (18)	C1B—C6B—C7B	121.17 (19)
C5A—C6A—C7A	121.7 (2)	C5B—C6B—C7B	119.61 (19)
N1A—C7A—C6A	115.71 (18)	N1B—C7B—C6B	116.18 (17)
N1A—C7A—S1A	123.48 (16)	N1B—C7B—S1B	123.30 (15)
C6A—C7A—S1A	120.81 (16)	C6B—C7B—S1B	120.51 (15)
N1A—C8A—C9A	109.07 (17)	N1B—C8B—C9B	109.48 (17)
N1A—C8A—C15A	109.12 (18)	N1B—C8B—C15B	109.46 (18)
C9A—C8A—C15A	115.40 (19)	C9B—C8B—C15B	115.39 (19)
N1A—C8A—H8AA	107.7	N1B—C8B—H8BA	107.4
C9A—C8A—H8AA	107.7	C9B—C8B—H8BA	107.4
C15A—C8A—H8AA	107.7	C15B—C8B—H8BA	107.4
C10A—C9A—C14A	118.2 (2)	C10B—C9B—C14B	118.5 (2)
C10A—C9A—C8A	122.1 (2)	C10B—C9B—C8B	121.9 (2)
C14A—C9A—C8A	119.7 (2)	C14B—C9B—C8B	119.7 (2)
C11A—C10A—C9A	120.4 (2)	C11B—C10B—C9B	120.6 (2)
C11A—C10A—H10A	119.8	C11B—C10B—H10B	119.7
C9A—C10A—H10A	119.8	C9B—C10B—H10B	119.7
C12A—C11A—C10A	120.8 (2)	C12B—C11B—C10B	120.6 (2)
C12A—C11A—H11A	119.6	C12B—C11B—H11B	119.7
C10A—C11A—H11A	119.6	C10B—C11B—H11B	119.7
C11A—C12A—C13A	119.0 (2)	C13B—C12B—C11B	119.5 (2)
C11A—C12A—H12A	120.5	C13B—C12B—H12B	120.3
C13A—C12A—H12A	120.5	C11B—C12B—H12B	120.3
C14A—C13A—C12A	120.3 (2)	C12B—C13B—C14B	120.2 (2)
C14A—C13A—H13A	119.8	C12B—C13B—H13B	119.9
C12A—C13A—H13A	119.8	C14B—C13B—H13B	119.9
C13A—C14A—C9A	121.3 (2)	C13B—C14B—C9B	120.7 (2)
C13A—C14A—H14A	119.4	C13B—C14B—H14B	119.6
C9A—C14A—H14A	119.4	C9B—C14B—H14B	119.6
C8A—C15A—H15A	109.5	C8B—C15B—H15D	109.5
C8A—C15A—H15B	109.5	C8B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C8A—C15A—H15C	109.5	C8B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C6A—C1A—C2A—C3A	−0.6 (4)	C6B—C1B—C2B—C3B	0.0 (3)
C1A—C2A—C3A—C4A	0.2 (4)	C1B—C2B—C3B—C4B	−0.1 (4)
C2A—C3A—C4A—C5A	−0.8 (4)	C2B—C3B—C4B—C5B	0.4 (4)
C3A—C4A—C5A—C6A	1.7 (3)	C3B—C4B—C5B—C6B	−0.5 (4)
C2A—C1A—C6A—C5A	1.6 (3)	C2B—C1B—C6B—C5B	−0.1 (3)
C2A—C1A—C6A—C7A	−178.0 (2)	C2B—C1B—C6B—C7B	−179.8 (2)
C4A—C5A—C6A—C1A	−2.1 (3)	C4B—C5B—C6B—C1B	0.3 (3)
C4A—C5A—C6A—C7A	177.5 (2)	C4B—C5B—C6B—C7B	180.0 (2)
C8A—N1A—C7A—C6A	−174.60 (19)	C8B—N1B—C7B—C6B	175.5 (2)
C8A—N1A—C7A—S1A	4.8 (3)	C8B—N1B—C7B—S1B	−3.6 (3)
C1A—C6A—C7A—N1A	149.5 (2)	C1B—C6B—C7B—N1B	−34.8 (3)
C5A—C6A—C7A—N1A	−30.0 (3)	C5B—C6B—C7B—N1B	145.5 (2)
C1A—C6A—C7A—S1A	−29.9 (3)	C1B—C6B—C7B—S1B	144.27 (19)
C5A—C6A—C7A—S1A	150.53 (18)	C5B—C6B—C7B—S1B	−35.4 (3)
C7A—N1A—C8A—C9A	106.5 (2)	C7B—N1B—C8B—C9B	149.3 (2)
C7A—N1A—C8A—C15A	−126.6 (2)	C7B—N1B—C8B—C15B	−83.3 (3)
N1A—C8A—C9A—C10A	142.6 (2)	N1B—C8B—C9B—C10B	133.5 (2)
C15A—C8A—C9A—C10A	19.4 (3)	C15B—C8B—C9B—C10B	9.5 (3)
N1A—C8A—C9A—C14A	−38.2 (3)	N1B—C8B—C9B—C14B	−47.8 (2)
C15A—C8A—C9A—C14A	−161.38 (19)	C15B—C8B—C9B—C14B	−171.83 (18)
C14A—C9A—C10A—C11A	0.2 (3)	C14B—C9B—C10B—C11B	1.8 (3)
C8A—C9A—C10A—C11A	179.42 (19)	C8B—C9B—C10B—C11B	−179.59 (19)
C9A—C10A—C11A—C12A	−0.8 (3)	C9B—C10B—C11B—C12B	−1.1 (3)
C10A—C11A—C12A—C13A	0.6 (3)	C10B—C11B—C12B—C13B	−0.2 (3)
C11A—C12A—C13A—C14A	0.2 (4)	C11B—C12B—C13B—C14B	0.6 (3)
C12A—C13A—C14A—C9A	−0.8 (4)	C12B—C13B—C14B—C9B	0.1 (3)
C10A—C9A—C14A—C13A	0.7 (3)	C10B—C9B—C14B—C13B	−1.3 (3)
C8A—C9A—C14A—C13A	−178.6 (2)	C8B—C9B—C14B—C13B	180.00 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···S1B^i	0.83 (3)	2.65 (3)	3.4353 (18)	160 (3)
N1B—H1NB···S1A^ii	0.83 (3)	2.78 (3)	3.4803 (18)	143 (3)
C1A—H1AA···S1A	0.93	2.76	3.126 (2)	105
C8A—H8AA···S1A	0.98	2.63	3.138 (2)	113
C5B—H5BA···S1B	0.93	2.83	3.152 (2)	102
C8B—H8BA···S1B	0.98	2.71	3.109 (2)	105
C14B—H14B···Cg1^iii	0.93	2.83	3.547 (2)	135
C13A—H13A···Cg2^iv	0.93	2.97	3.637 (3)	130
C15B—H15F···Cg3^iii	0.96	3.11	3.845 (2)	134
C8A—H8AA···Cg4^iv	0.98	2.98	3.852 (2)	148
C2B—H2BA···Cg4^v	0.93	3.13	3.764 (2)	127

Symmetry codes: (i) x−1, y, z; (ii) −x+3/2, −y+1, z−1/2; (iii) x+1, y+1, z; (iv) −x+3/2, −y+1, z+1/2; (v) −x+5/2, −y+1, z−1/2.