(5S,6R)-5-Methyl-6-phenyl-4-propyl-1,3,4-oxadiazinane-2-thione.

The title mol-ecule, C(13)H(18)N(2)OS, is an oxadiazinanthione derived from (1R,2S)-norephedrine. There are two molecules in the asymmetric. Both adopt roughly half-chair conformations; however, the 5-position carbon orients out of opposite faces of the oxadiazinanthiones plane in the two molecules. In the crystal structure, they are oriented as a dimer linked by a pair of N-H⋯S hydrogen bonds. The absolute configuration has been established from anomalous dispersion and confirms the known stereochemistry based on the synthetic procedure.

Related literature

For background, see: Hitchcock et al. (2002 ▶, 2008 ▶); Trepanier et al. (1968 ▶). For related compounds, see: Burgeson et al. (2004 ▶); Casper, Blackburn et al. (2002 ▶); Casper, Burgeson et al. (2002 ▶); Cremer & Pople (1975 ▶); Ferrence et al. (2003 ▶); Hitchcock et al. (2001 ▶, 2004 ▶); Rodrigues et al. (2005 ▶, 2006 ▶); Squire et al. (2005 ▶); Szczepura et al. (2004 ▶). For structural analysis, see: Boeyens (1978 ▶); Bruno et al. (2004 ▶); Cremer & Pople (1975 ▶); Spek (2009 ▶).

Experimental

Crystal data

C13H18N2OS

M = 250.36

Monoclinic,

a = 12.5888 (6) Å

b = 8.0648 (4) Å

c = 14.2862 (7) Å

β = 112.4488 (7)°

V = 1340.51 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 193 K

0.45 × 0.3 × 0.26 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 1999 ▶) T min = 0.812, T max = 0.943

10254 measured reflections

5344 independent reflections

5154 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.076

S = 1.03

5344 reflections

315 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶)

Flack parameter: 0.03 (4)

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (McMahon & Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019382/fj2214sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019382/fj2214Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Enhanced figure: interactive version of Fig. 3

C13H18N2OS	F(000) = 536
Mr = 250.36	Dx = 1.24 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4757 reflections
a = 12.5888 (6) Å	θ = 2.7–26.4°
b = 8.0648 (4) Å	µ = 0.23 mm−1
c = 14.2862 (7) Å	T = 193 K
β = 112.4488 (7)°	Prism, colourless
V = 1340.51 (11) Å3	0.45 × 0.3 × 0.26 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	5154 reflections with I > 2σ(I)
graphite	Rint = 0.016
ω scans	θmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 1999)	h = −15→15
Tmin = 0.812, Tmax = 0.943	k = −9→10
10254 measured reflections	l = −17→17
5344 independent reflections

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0464P)2 + 0.1813P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.028	(Δ/σ)max = 0.001
wR(F2) = 0.076	Δρmax = 0.23 e Å−3
S = 1.03	Δρmin = −0.19 e Å−3
5344 reflections	Absolute structure: Flack (1983)
315 parameters	Flack parameter: 0.03 (4)
1 restraint

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.

	x	y	z	Uiso*/Ueq
H3	0.5801 (17)	0.487 (3)	0.3637 (14)	0.037 (5)*
H53	0.4291 (18)	0.298 (3)	0.1944 (15)	0.044 (6)*
O1	0.82647 (9)	0.40738 (15)	0.38779 (8)	0.0317 (2)
C2	0.71123 (12)	0.3987 (2)	0.35160 (11)	0.0266 (3)
N3	0.65394 (10)	0.49797 (16)	0.38728 (9)	0.0277 (3)
N4	0.70414 (10)	0.60668 (16)	0.47180 (9)	0.0260 (3)
C5	0.81231 (12)	0.67014 (19)	0.46870 (12)	0.0284 (3)
H5	0.7956	0.7334	0.4044	0.034*
C6	0.88793 (11)	0.5206 (2)	0.47089 (11)	0.0281 (3)
H6	0.9556	0.5635	0.458	0.034*
C7	0.93458 (12)	0.4261 (2)	0.56893 (12)	0.0292 (3)
C8	0.86992 (13)	0.3065 (2)	0.59413 (12)	0.0337 (3)
H8	0.7935	0.2837	0.5487	0.04*
C9	0.91621 (16)	0.2203 (2)	0.68504 (13)	0.0402 (4)
H9	0.8718	0.1386	0.7015	0.048*
C10	1.02754 (15)	0.2541 (3)	0.75165 (13)	0.0427 (4)
H10	1.0599	0.1942	0.8134	0.051*
C11	1.09113 (15)	0.3742 (3)	0.72841 (13)	0.0432 (4)
H11	1.1666	0.3988	0.7751	0.052*
C12	1.04608 (13)	0.4594 (2)	0.63761 (12)	0.0365 (4)
H12	1.0912	0.5409	0.6219	0.044*
C13	0.87021 (14)	0.7838 (2)	0.55843 (13)	0.0384 (4)
H13A	0.8199	0.8784	0.5548	0.058*
H13B	0.9431	0.8239	0.557	0.058*
H13C	0.8851	0.7227	0.6214	0.058*
C14	0.61975 (13)	0.7372 (2)	0.46634 (11)	0.0301 (3)
H14A	0.6508	0.8031	0.5295	0.036*
H14B	0.5488	0.6824	0.465	0.036*
C15	0.58656 (15)	0.8565 (2)	0.37746 (13)	0.0386 (4)
H15A	0.5536	0.794	0.3131	0.046*
H15B	0.6557	0.916	0.3782	0.046*
C16	0.4989 (2)	0.9805 (3)	0.38432 (19)	0.0642 (6)
H16A	0.4772	1.0565	0.3265	0.096*
H16B	0.5325	1.0438	0.4474	0.096*
H16C	0.4306	0.9212	0.3835	0.096*
S17	0.64745 (3)	0.25776 (5)	0.25998 (3)	0.03521 (10)
O51	0.18836 (8)	0.39587 (13)	0.16424 (8)	0.0282 (2)
C52	0.30313 (12)	0.39369 (19)	0.20313 (11)	0.0261 (3)
N53	0.35868 (11)	0.29154 (17)	0.16570 (9)	0.0277 (3)
N54	0.30882 (10)	0.15932 (16)	0.09668 (9)	0.0273 (3)
C55	0.19357 (12)	0.12386 (19)	0.09575 (12)	0.0270 (3)
H55	0.1528	0.0502	0.0366	0.032*
C56	0.12635 (11)	0.28685 (18)	0.07989 (11)	0.0252 (3)
H56	0.1237	0.3395	0.0156	0.03*
C57	0.00531 (11)	0.27209 (18)	0.07641 (10)	0.0252 (3)
C58	−0.02242 (13)	0.3144 (2)	0.15848 (11)	0.0331 (3)
H58	0.0358	0.3553	0.2186	0.04*
C59	−0.13361 (14)	0.2977 (2)	0.15410 (13)	0.0371 (4)
H59	−0.1513	0.3264	0.211	0.045*
C60	−0.21914 (13)	0.2390 (2)	0.06632 (13)	0.0355 (3)
H60	−0.2956	0.2271	0.063	0.043*
C61	−0.19292 (13)	0.1979 (2)	−0.01602 (13)	0.0334 (3)
H61	−0.2517	0.1584	−0.0762	0.04*
C62	−0.08151 (13)	0.21385 (19)	−0.01173 (12)	0.0289 (3)
H62	−0.0642	0.1851	−0.0688	0.035*
C63	0.20153 (14)	0.0328 (2)	0.19114 (12)	0.0351 (3)
H63A	0.2454	−0.0698	0.1975	0.053*
H63B	0.124	0.0061	0.1873	0.053*
H63C	0.2403	0.1034	0.2503	0.053*
C64	0.31096 (13)	0.1969 (2)	−0.00361 (11)	0.0323 (3)
H64A	0.2733	0.3053	−0.0271	0.039*
H64B	0.2663	0.1114	−0.0525	0.039*
C65	0.43186 (14)	0.2023 (3)	−0.00219 (13)	0.0449 (5)
H65A	0.4725	0.0983	0.0277	0.054*
H65B	0.4743	0.2957	0.0408	0.054*
C66	0.43043 (18)	0.2236 (4)	−0.10884 (15)	0.0600 (6)
H66A	0.5095	0.226	−0.1058	0.09*
H66B	0.3918	0.3277	−0.1379	0.09*
H66C	0.3891	0.1306	−0.1513	0.09*
S67	0.36887 (3)	0.52486 (5)	0.29914 (3)	0.03515 (10)

	U11	U22	U33	U12	U13	U23
O1	0.0211 (5)	0.0432 (7)	0.0292 (5)	0.0010 (4)	0.0078 (4)	−0.0076 (5)
C2	0.0228 (7)	0.0307 (8)	0.0260 (7)	−0.0016 (6)	0.0090 (6)	0.0002 (6)
N3	0.0196 (6)	0.0315 (7)	0.0300 (6)	−0.0015 (5)	0.0072 (5)	−0.0047 (5)
N4	0.0235 (6)	0.0285 (7)	0.0252 (6)	−0.0016 (5)	0.0083 (5)	−0.0027 (5)
C5	0.0240 (7)	0.0301 (8)	0.0301 (7)	−0.0016 (6)	0.0093 (6)	0.0020 (6)
C6	0.0196 (6)	0.0349 (8)	0.0288 (7)	−0.0049 (6)	0.0081 (5)	−0.0034 (7)
C7	0.0230 (7)	0.0330 (8)	0.0310 (8)	0.0022 (6)	0.0096 (6)	−0.0041 (6)
C8	0.0276 (7)	0.0352 (8)	0.0355 (8)	−0.0006 (6)	0.0089 (6)	−0.0010 (7)
C9	0.0446 (10)	0.0385 (10)	0.0410 (9)	0.0034 (7)	0.0201 (8)	0.0034 (8)
C10	0.0461 (9)	0.0476 (10)	0.0314 (8)	0.0139 (9)	0.0112 (7)	0.0050 (8)
C11	0.0313 (8)	0.0539 (11)	0.0350 (9)	0.0074 (8)	0.0021 (7)	−0.0035 (8)
C12	0.0255 (8)	0.0433 (9)	0.0364 (8)	−0.0012 (7)	0.0070 (6)	−0.0025 (7)
C13	0.0339 (8)	0.0358 (9)	0.0408 (9)	−0.0067 (7)	0.0089 (7)	−0.0054 (7)
C14	0.0286 (7)	0.0344 (8)	0.0282 (7)	0.0022 (6)	0.0119 (6)	−0.0039 (6)
C15	0.0381 (9)	0.0367 (9)	0.0407 (9)	0.0073 (7)	0.0146 (7)	0.0047 (7)
C16	0.0586 (13)	0.0610 (15)	0.0805 (15)	0.0297 (11)	0.0349 (12)	0.0218 (12)
S17	0.02566 (18)	0.0418 (2)	0.0374 (2)	−0.00325 (16)	0.01108 (15)	−0.01413 (17)
O51	0.0194 (5)	0.0265 (5)	0.0336 (6)	−0.0015 (4)	0.0045 (4)	−0.0038 (4)
C52	0.0217 (7)	0.0280 (8)	0.0261 (7)	−0.0011 (6)	0.0063 (6)	0.0034 (6)
N53	0.0190 (6)	0.0345 (7)	0.0256 (6)	−0.0024 (5)	0.0040 (5)	−0.0028 (5)
N54	0.0221 (6)	0.0291 (7)	0.0279 (6)	−0.0005 (5)	0.0063 (5)	−0.0024 (5)
C55	0.0228 (7)	0.0250 (7)	0.0307 (8)	−0.0020 (6)	0.0073 (6)	−0.0007 (6)
C56	0.0222 (7)	0.0258 (7)	0.0250 (6)	−0.0022 (6)	0.0062 (5)	−0.0001 (6)
C57	0.0209 (6)	0.0241 (7)	0.0272 (7)	−0.0002 (5)	0.0053 (5)	0.0020 (6)
C58	0.0273 (7)	0.0420 (9)	0.0256 (7)	−0.0035 (6)	0.0052 (6)	0.0004 (6)
C59	0.0327 (8)	0.0471 (10)	0.0348 (8)	−0.0014 (7)	0.0164 (7)	−0.0006 (7)
C60	0.0234 (7)	0.0362 (9)	0.0473 (9)	−0.0019 (6)	0.0139 (7)	−0.0004 (8)
C61	0.0229 (7)	0.0315 (8)	0.0388 (8)	−0.0038 (6)	0.0039 (6)	−0.0063 (7)
C62	0.0262 (7)	0.0282 (8)	0.0303 (7)	−0.0003 (6)	0.0086 (6)	−0.0045 (6)
C63	0.0316 (7)	0.0327 (8)	0.0397 (8)	0.0012 (7)	0.0123 (6)	0.0072 (7)
C64	0.0262 (7)	0.0392 (9)	0.0285 (7)	−0.0016 (6)	0.0072 (6)	−0.0055 (7)
C65	0.0295 (8)	0.0701 (13)	0.0359 (9)	0.0009 (8)	0.0135 (7)	−0.0035 (9)
C66	0.0442 (10)	0.1014 (18)	0.0394 (10)	−0.0052 (11)	0.0218 (8)	−0.0079 (12)
S67	0.02293 (17)	0.0437 (2)	0.03399 (19)	−0.00201 (16)	0.00548 (14)	−0.01305 (17)

O1—C2	1.3432 (17)	O51—C52	1.3355 (17)
O1—C6	1.4627 (18)	O51—C56	1.4548 (16)
C2—N3	1.305 (2)	C52—N53	1.319 (2)
C2—S17	1.6873 (15)	C52—S67	1.6788 (15)
N3—N4	1.4294 (17)	N53—N54	1.4250 (18)
N3—H3	0.86 (2)	N53—H53	0.82 (2)
N4—C5	1.4711 (18)	N54—C55	1.4739 (18)
N4—C14	1.476 (2)	N54—C64	1.475 (2)
C5—C13	1.517 (2)	C55—C63	1.517 (2)
C5—C6	1.530 (2)	C55—C56	1.533 (2)
C5—H5	1	C55—H55	1
C6—C7	1.503 (2)	C56—C57	1.5101 (18)
C6—H6	1	C56—H56	1
C7—C8	1.396 (2)	C57—C58	1.388 (2)
C7—C12	1.397 (2)	C57—C62	1.3963 (19)
C8—C9	1.390 (2)	C58—C59	1.384 (2)
C8—H8	0.95	C58—H58	0.95
C9—C10	1.388 (3)	C59—C60	1.388 (2)
C9—H9	0.95	C59—H59	0.95
C10—C11	1.375 (3)	C60—C61	1.378 (2)
C10—H10	0.95	C60—H60	0.95
C11—C12	1.384 (2)	C61—C62	1.386 (2)
C11—H11	0.95	C61—H61	0.95
C12—H12	0.95	C62—H62	0.95
C13—H13A	0.98	C63—H63A	0.98
C13—H13B	0.98	C63—H63B	0.98
C13—H13C	0.98	C63—H63C	0.98
C14—C15	1.519 (2)	C64—C65	1.515 (2)
C14—H14A	0.99	C64—H64A	0.99
C14—H14B	0.99	C64—H64B	0.99
C15—C16	1.520 (3)	C65—C66	1.527 (3)
C15—H15A	0.99	C65—H65A	0.99
C15—H15B	0.99	C65—H65B	0.99
C16—H16A	0.98	C66—H66A	0.98
C16—H16B	0.98	C66—H66B	0.98
C16—H16C	0.98	C66—H66C	0.98
C2—O1—C6	120.25 (12)	C52—O51—C56	119.32 (11)
N3—C2—O1	119.64 (13)	N53—C52—O51	119.77 (13)
N3—C2—S17	123.11 (11)	N53—C52—S67	123.55 (11)
O1—C2—S17	117.25 (11)	O51—C52—S67	116.68 (11)
C2—N3—N4	125.07 (12)	C52—N53—N54	125.90 (12)
C2—N3—H3	117.2 (13)	C52—N53—H53	113.1 (15)
N4—N3—H3	117.1 (13)	N54—N53—H53	120.0 (15)
N3—N4—C5	107.68 (11)	N53—N54—C55	108.87 (11)
N3—N4—C14	108.40 (11)	N53—N54—C64	110.61 (12)
C5—N4—C14	113.96 (12)	C55—N54—C64	114.47 (11)
N4—C5—C13	109.66 (13)	N54—C55—C63	111.02 (12)
N4—C5—C6	107.52 (12)	N54—C55—C56	108.73 (12)
C13—C5—C6	111.41 (12)	C63—C55—C56	113.03 (13)
N4—C5—H5	109.4	N54—C55—H55	108
C13—C5—H5	109.4	C63—C55—H55	108
C6—C5—H5	109.4	C56—C55—H55	108
O1—C6—C7	109.73 (13)	O51—C56—C57	106.89 (11)
O1—C6—C5	110.08 (11)	O51—C56—C55	107.73 (11)
C7—C6—C5	115.94 (12)	C57—C56—C55	115.50 (12)
O1—C6—H6	106.9	O51—C56—H56	108.9
C7—C6—H6	106.9	C57—C56—H56	108.9
C5—C6—H6	106.9	C55—C56—H56	108.9
C8—C7—C12	118.68 (15)	C58—C57—C62	118.80 (13)
C8—C7—C6	122.14 (13)	C58—C57—C56	121.94 (12)
C12—C7—C6	119.17 (14)	C62—C57—C56	119.26 (13)
C9—C8—C7	120.61 (15)	C59—C58—C57	120.97 (14)
C9—C8—H8	119.7	C59—C58—H58	119.5
C7—C8—H8	119.7	C57—C58—H58	119.5
C10—C9—C8	119.73 (17)	C58—C59—C60	119.77 (15)
C10—C9—H9	120.1	C58—C59—H59	120.1
C8—C9—H9	120.1	C60—C59—H59	120.1
C11—C10—C9	120.09 (16)	C61—C60—C59	119.83 (14)
C11—C10—H10	120	C61—C60—H60	120.1
C9—C10—H10	120	C59—C60—H60	120.1
C10—C11—C12	120.52 (16)	C60—C61—C62	120.54 (14)
C10—C11—H11	119.7	C60—C61—H61	119.7
C12—C11—H11	119.7	C62—C61—H61	119.7
C11—C12—C7	120.34 (17)	C61—C62—C57	120.09 (14)
C11—C12—H12	119.8	C61—C62—H62	120
C7—C12—H12	119.8	C57—C62—H62	120
C5—C13—H13A	109.5	C55—C63—H63A	109.5
C5—C13—H13B	109.5	C55—C63—H63B	109.5
H13A—C13—H13B	109.5	H63A—C63—H63B	109.5
C5—C13—H13C	109.5	C55—C63—H63C	109.5
H13A—C13—H13C	109.5	H63A—C63—H63C	109.5
H13B—C13—H13C	109.5	H63B—C63—H63C	109.5
N4—C14—C15	117.29 (12)	N54—C64—C65	112.58 (13)
N4—C14—H14A	108	N54—C64—H64A	109.1
C15—C14—H14A	108	C65—C64—H64A	109.1
N4—C14—H14B	108	N54—C64—H64B	109.1
C15—C14—H14B	108	C65—C64—H64B	109.1
H14A—C14—H14B	107.2	H64A—C64—H64B	107.8
C14—C15—C16	109.73 (16)	C64—C65—C66	111.17 (15)
C14—C15—H15A	109.7	C64—C65—H65A	109.4
C16—C15—H15A	109.7	C66—C65—H65A	109.4
C14—C15—H15B	109.7	C64—C65—H65B	109.4
C16—C15—H15B	109.7	C66—C65—H65B	109.4
H15A—C15—H15B	108.2	H65A—C65—H65B	108
C15—C16—H16A	109.5	C65—C66—H66A	109.5
C15—C16—H16B	109.5	C65—C66—H66B	109.5
H16A—C16—H16B	109.5	H66A—C66—H66B	109.5
C15—C16—H16C	109.5	C65—C66—H66C	109.5
H16A—C16—H16C	109.5	H66A—C66—H66C	109.5
H16B—C16—H16C	109.5	H66B—C66—H66C	109.5
C6—O1—C2—N3	3.6 (2)	C56—O51—C52—N53	−0.9 (2)
C6—O1—C2—S17	−176.82 (11)	C56—O51—C52—S67	179.09 (10)
O1—C2—N3—N4	−7.4 (2)	O51—C52—N53—N54	−11.2 (2)
S17—C2—N3—N4	173.03 (11)	S67—C52—N53—N54	168.81 (11)
C2—N3—N4—C5	36.25 (18)	C52—N53—N54—C55	−15.85 (19)
C2—N3—N4—C14	159.97 (14)	C52—N53—N54—C64	110.75 (16)
N3—N4—C5—C13	−178.87 (12)	N53—N54—C55—C63	−74.51 (15)
C14—N4—C5—C13	60.85 (16)	C64—N54—C55—C63	161.14 (14)
N3—N4—C5—C6	−57.59 (14)	N53—N54—C55—C56	50.43 (15)
C14—N4—C5—C6	−177.87 (11)	C64—N54—C55—C56	−73.92 (16)
C2—O1—C6—C7	100.10 (15)	C52—O51—C56—C57	160.86 (12)
C2—O1—C6—C5	−28.65 (18)	C52—O51—C56—C55	36.15 (16)
N4—C5—C6—O1	55.69 (15)	N54—C55—C56—O51	−60.99 (14)
C13—C5—C6—O1	175.87 (12)	C63—C55—C56—O51	62.77 (15)
N4—C5—C6—C7	−69.59 (16)	N54—C55—C56—C57	179.65 (11)
C13—C5—C6—C7	50.59 (17)	C63—C55—C56—C57	−56.60 (17)
O1—C6—C7—C8	−43.15 (19)	O51—C56—C57—C58	−17.70 (19)
C5—C6—C7—C8	82.32 (19)	C55—C56—C57—C58	102.13 (17)
O1—C6—C7—C12	137.21 (14)	O51—C56—C57—C62	162.47 (13)
C5—C6—C7—C12	−97.32 (17)	C55—C56—C57—C62	−77.70 (17)
C12—C7—C8—C9	−1.0 (2)	C62—C57—C58—C59	0.7 (2)
C6—C7—C8—C9	179.35 (15)	C56—C57—C58—C59	−179.12 (15)
C7—C8—C9—C10	0.3 (3)	C57—C58—C59—C60	−0.4 (3)
C8—C9—C10—C11	1.0 (3)	C58—C59—C60—C61	−0.2 (3)
C9—C10—C11—C12	−1.6 (3)	C59—C60—C61—C62	0.4 (3)
C10—C11—C12—C7	0.9 (3)	C60—C61—C62—C57	−0.1 (2)
C8—C7—C12—C11	0.4 (2)	C58—C57—C62—C61	−0.5 (2)
C6—C7—C12—C11	−179.97 (16)	C56—C57—C62—C61	179.38 (14)
N3—N4—C14—C15	−65.19 (17)	N53—N54—C64—C65	66.76 (17)
C5—N4—C14—C15	54.69 (18)	C55—N54—C64—C65	−169.82 (14)
N4—C14—C15—C16	179.66 (16)	N54—C64—C65—C66	174.12 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···S67	0.86 (2)	2.48 (2)	3.3257 (14)	167 (2)
N53—H53···S17	0.82 (2)	2.56 (2)	3.3711 (15)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯S67	0.86 (2)	2.48 (2)	3.3257 (14)	167 (2)
N53—H53⋯S17	0.82 (2)	2.56 (2)	3.3711 (15)	167 (2)