11-[3-(Dimethyl-amino)prop-yl]-6,11-dihydro-dibenzo[b,e]thiepin-11-ol.

There are two independent mol-ecules (A and B) in the asymmetric unit of the title compound, C(19)H(23)NOS. In each mol-ecule, the seven-membered thiepine ring is bent into a slightly twisted V-shape. The dihedral angles between the mean planes of the two benzene rings fused to the thiepine ring are 75.7 (5) in mol-ecule A and 73.8 (4)° in mol-ecule B. In both mol-ecules, an intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, weak inter-molecular C-H⋯O and C-H⋯π-ring inter-actions are observed.

Related literature

For related structures, see: Bandoli & Nicolini, (1982 ▶); Blaton et al. (1995 ▶); Ieawsuwan et al. (2006 ▶); Linden et al. (2004 ▶); Portalone et al. (2007 ▶); Roszak et al. (1996 ▶); Rudorf et al. (1999 ▶); Yoshinari & Konno, (2009 ▶); Zhang et al. (2008 ▶,2008a ▶). For related background, see: Rudorf et al. (1999 ▶). For antidepressant and anti-inflammatory properties, see: Rajsner et al. (1969 ▶, 1971 ▶); Rooks et al. (1980 ▶); Tomascovic et al. (2000 ▶); Truce et al. (1956 ▶). For pharmacological synthesis and studies, see: Ikuo et al. (1978 ▶); Uchida et al. (1979 ▶); Wyatt et al. (2006 ▶). For NMR, Ir and X-ray studies, see: Kolehmainen et al. (2007 ▶). For density functional theory (DFT), see: Becke (1988 ▶, 1993 ▶); Frisch et al. (2004 ▶); Hehre et al. (1986 ▶); Lee et al. (1988 ▶); Schmidt & Polik (2007 ▶).

Experimental

Crystal data

C19H23NOS

M = 313.44

Monoclinic,

a = 7.7215 (4) Å

b = 15.3729 (10) Å

c = 27.9274 (16) Å

β = 95.401 (6)°

V = 3300.3 (3) Å3

Z = 8

Cu Kα radiation

μ = 1.74 mm−1

T = 110 K

0.51 × 0.42 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.432, T max = 1.000

14666 measured reflections

6565 independent reflections

5490 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.153

S = 1.05

6565 reflections

403 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.56 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053434/lh2968sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053434/lh2968Isup2.hkl

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

C19H23NOS	F(000) = 1344
Mr = 313.44	Dx = 1.262 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 6805 reflections
a = 7.7215 (4) Å	θ = 4.3–74.0°
b = 15.3729 (10) Å	µ = 1.74 mm−1
c = 27.9274 (16) Å	T = 110 K
β = 95.401 (6)°	Plate, colorless
V = 3300.3 (3) Å3	0.51 × 0.42 × 0.14 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	6565 independent reflections
Radiation source: Enhance (Cu) X-ray Source	5490 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 10.5081 pixels mm-1	θmax = 74.2°, θmin = 4.3°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −13→19
Tmin = 0.432, Tmax = 1.000	l = −17→34
14666 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1079P)2 + 0.6589P] where P = (Fo2 + 2Fc2)/3
6565 reflections	(Δ/σ)max = 0.001
403 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1A	0.69626 (7)	0.25999 (3)	0.288172 (19)	0.02978 (15)
O1A	0.91923 (17)	0.54941 (9)	0.28401 (5)	0.0240 (3)
H1A	1.0075	0.5603	0.2696	0.029*
N1A	1.2061 (2)	0.56334 (11)	0.23664 (6)	0.0242 (4)
C1A	0.7385 (2)	0.44069 (13)	0.31337 (6)	0.0189 (4)
C2A	0.6889 (2)	0.50798 (13)	0.34289 (6)	0.0230 (4)
H2AA	0.7418	0.5635	0.3408	0.028*
C3A	0.5643 (3)	0.49613 (15)	0.37524 (7)	0.0276 (4)
H3AA	0.5350	0.5429	0.3952	0.033*
C4A	0.4833 (3)	0.41658 (15)	0.37828 (7)	0.0284 (4)
H4AA	0.3984	0.4079	0.4003	0.034*
C5A	0.5275 (3)	0.34982 (14)	0.34876 (7)	0.0264 (4)
H5AA	0.4697	0.2955	0.3502	0.032*
C6A	0.6554 (2)	0.35985 (13)	0.31669 (6)	0.0202 (4)
C7A	0.7862 (3)	0.28132 (13)	0.23129 (7)	0.0238 (4)
H7AA	0.9147	0.2814	0.2370	0.029*
H7AB	0.7527	0.2330	0.2089	0.029*
C8A	0.7295 (2)	0.36527 (13)	0.20746 (6)	0.0202 (4)
C9A	0.6275 (3)	0.36079 (15)	0.16343 (7)	0.0280 (4)
H9AA	0.5927	0.3055	0.1508	0.034*
C10A	0.5764 (3)	0.43455 (17)	0.13802 (7)	0.0331 (5)
H10A	0.5075	0.4301	0.1081	0.040*
C11A	0.6263 (3)	0.51514 (16)	0.15646 (7)	0.0306 (5)
H11A	0.5926	0.5665	0.1391	0.037*
C12A	0.7258 (2)	0.52091 (13)	0.20050 (7)	0.0232 (4)
H12A	0.7588	0.5766	0.2129	0.028*
C13A	0.7782 (2)	0.44720 (12)	0.22683 (6)	0.0170 (4)
C14A	0.8737 (2)	0.46053 (12)	0.27754 (6)	0.0181 (4)
C15A	1.0403 (2)	0.40533 (13)	0.28923 (6)	0.0207 (4)
H15A	1.1021	0.4278	0.3194	0.025*
H15B	1.0046	0.3448	0.2955	0.025*
C16A	1.1698 (2)	0.40312 (13)	0.25052 (7)	0.0218 (4)
H16A	1.2402	0.3494	0.2550	0.026*
H16B	1.1027	0.3994	0.2186	0.026*
C17A	1.2933 (2)	0.48049 (13)	0.25020 (7)	0.0241 (4)
H17A	1.3558	0.4868	0.2826	0.029*
H17B	1.3810	0.4683	0.2274	0.029*
C18A	1.1570 (3)	0.56816 (15)	0.18463 (7)	0.0296 (5)
H18A	1.0974	0.6234	0.1769	0.044*
H18B	1.0791	0.5197	0.1748	0.044*
H18C	1.2618	0.5646	0.1675	0.044*
C19A	1.3169 (3)	0.63736 (16)	0.25201 (10)	0.0396 (6)
H19A	1.2540	0.6917	0.2442	0.059*
H19B	1.4230	0.6358	0.2353	0.059*
H19C	1.3477	0.6342	0.2868	0.059*
S1B	0.66729 (7)	0.22246 (4)	0.627252 (18)	0.03356 (16)
O1B	0.39362 (17)	0.32974 (9)	0.47928 (5)	0.0224 (3)
H1B	0.2941	0.3119	0.4691	0.027*
N1B	0.0713 (2)	0.27183 (13)	0.45327 (6)	0.0272 (4)
C1B	0.6076 (2)	0.33566 (12)	0.54588 (6)	0.0194 (4)
C2B	0.6575 (2)	0.41167 (13)	0.52343 (7)	0.0225 (4)
H2BA	0.5966	0.4284	0.4937	0.027*
C3B	0.7936 (3)	0.46361 (14)	0.54324 (8)	0.0269 (4)
H3BA	0.8237	0.5154	0.5274	0.032*
C4B	0.8849 (3)	0.43913 (14)	0.58631 (8)	0.0296 (5)
H4BA	0.9773	0.4743	0.6003	0.036*
C5B	0.8406 (3)	0.36365 (14)	0.60857 (7)	0.0279 (4)
H5BA	0.9048	0.3467	0.6378	0.033*
C6B	0.7032 (2)	0.31114 (13)	0.58920 (7)	0.0227 (4)
C7B	0.5684 (3)	0.13299 (14)	0.59244 (7)	0.0292 (4)
H7BA	0.6145	0.0780	0.6070	0.035*
H7BB	0.4418	0.1340	0.5955	0.035*
C8B	0.5951 (2)	0.13126 (13)	0.53919 (7)	0.0249 (4)
C9B	0.6839 (3)	0.05921 (14)	0.52276 (9)	0.0340 (5)
H9BA	0.7316	0.0173	0.5453	0.041*
C10B	0.7035 (3)	0.04778 (15)	0.47439 (10)	0.0382 (6)
H10B	0.7637	−0.0015	0.4638	0.046*
C11B	0.6349 (3)	0.10843 (16)	0.44183 (8)	0.0341 (5)
H11B	0.6440	0.1002	0.4084	0.041*
C12B	0.5524 (2)	0.18169 (14)	0.45762 (7)	0.0257 (4)
H12B	0.5087	0.2240	0.4348	0.031*
C13B	0.5316 (2)	0.19501 (13)	0.50640 (7)	0.0199 (4)
C14B	0.4538 (2)	0.28306 (12)	0.52111 (6)	0.0187 (4)
C15B	0.3036 (2)	0.27781 (14)	0.55385 (7)	0.0231 (4)
H15C	0.3525	0.2592	0.5863	0.028*
H15D	0.2554	0.3370	0.5570	0.028*
C16B	0.1534 (2)	0.21639 (14)	0.53708 (7)	0.0258 (4)
H16C	0.2030	0.1642	0.5227	0.031*
H16D	0.0976	0.1970	0.5657	0.031*
C17B	0.0125 (2)	0.25346 (13)	0.50080 (7)	0.0220 (4)
H17C	−0.0853	0.2116	0.4968	0.026*
H17D	−0.0321	0.3080	0.5140	0.026*
C18B	0.0944 (3)	0.1914 (2)	0.42672 (9)	0.0515 (8)
H18D	0.1890	0.1573	0.4433	0.077*
H18E	0.1232	0.2054	0.3942	0.077*
H18F	−0.0136	0.1575	0.4248	0.077*
C19B	−0.0530 (3)	0.3298 (2)	0.42629 (9)	0.0479 (7)
H19D	−0.0118	0.3430	0.3950	0.072*
H19E	−0.0635	0.3839	0.4444	0.072*
H19F	−0.1668	0.3012	0.4215	0.072*

	U11	U22	U33	U12	U13	U23
S1A	0.0386 (3)	0.0189 (2)	0.0344 (3)	−0.0007 (2)	0.0165 (2)	0.00348 (19)
O1A	0.0191 (7)	0.0210 (7)	0.0333 (7)	−0.0042 (5)	0.0094 (5)	−0.0068 (6)
N1A	0.0208 (8)	0.0233 (8)	0.0293 (8)	−0.0028 (6)	0.0070 (6)	−0.0039 (7)
C1A	0.0150 (8)	0.0269 (9)	0.0148 (8)	0.0016 (7)	0.0015 (6)	0.0003 (7)
C2A	0.0194 (9)	0.0291 (10)	0.0208 (8)	0.0002 (7)	0.0025 (7)	−0.0039 (8)
C3A	0.0247 (10)	0.0398 (12)	0.0188 (8)	0.0059 (9)	0.0047 (7)	−0.0055 (8)
C4A	0.0240 (10)	0.0434 (12)	0.0189 (8)	0.0055 (9)	0.0078 (7)	0.0078 (8)
C5A	0.0249 (10)	0.0315 (11)	0.0234 (9)	0.0026 (8)	0.0059 (7)	0.0092 (8)
C6A	0.0209 (9)	0.0222 (9)	0.0177 (8)	0.0033 (7)	0.0022 (7)	0.0030 (7)
C7A	0.0269 (10)	0.0198 (9)	0.0258 (9)	0.0003 (7)	0.0088 (7)	−0.0037 (7)
C8A	0.0184 (9)	0.0251 (10)	0.0177 (8)	−0.0006 (7)	0.0051 (7)	−0.0007 (7)
C9A	0.0237 (10)	0.0395 (12)	0.0210 (9)	−0.0004 (9)	0.0031 (7)	−0.0090 (8)
C10A	0.0236 (10)	0.0594 (15)	0.0164 (8)	0.0080 (10)	0.0018 (7)	0.0004 (9)
C11A	0.0210 (10)	0.0468 (13)	0.0254 (9)	0.0101 (9)	0.0091 (7)	0.0159 (9)
C12A	0.0166 (8)	0.0265 (10)	0.0277 (9)	0.0028 (7)	0.0089 (7)	0.0068 (8)
C13A	0.0121 (8)	0.0230 (9)	0.0169 (8)	0.0016 (7)	0.0065 (6)	0.0015 (7)
C14A	0.0166 (8)	0.0192 (9)	0.0190 (8)	−0.0008 (7)	0.0041 (6)	−0.0021 (7)
C15A	0.0168 (8)	0.0257 (10)	0.0198 (8)	0.0013 (7)	0.0026 (6)	−0.0003 (7)
C16A	0.0171 (9)	0.0246 (9)	0.0242 (9)	0.0036 (7)	0.0049 (7)	0.0001 (7)
C17A	0.0160 (8)	0.0306 (10)	0.0260 (9)	0.0008 (8)	0.0033 (7)	−0.0002 (8)
C18A	0.0264 (10)	0.0345 (11)	0.0293 (10)	0.0043 (8)	0.0103 (8)	0.0074 (9)
C19A	0.0314 (12)	0.0322 (12)	0.0572 (14)	−0.0121 (10)	0.0155 (11)	−0.0117 (11)
S1B	0.0336 (3)	0.0426 (3)	0.0233 (3)	0.0001 (2)	−0.00317 (19)	0.0080 (2)
O1B	0.0184 (6)	0.0281 (7)	0.0199 (6)	−0.0033 (5)	−0.0022 (5)	0.0059 (5)
N1B	0.0221 (8)	0.0414 (10)	0.0180 (7)	−0.0099 (7)	0.0010 (6)	0.0005 (7)
C1B	0.0158 (8)	0.0226 (9)	0.0200 (8)	0.0041 (7)	0.0026 (7)	−0.0039 (7)
C2B	0.0179 (9)	0.0246 (9)	0.0248 (9)	0.0030 (7)	0.0018 (7)	−0.0044 (8)
C3B	0.0213 (9)	0.0237 (9)	0.0357 (10)	0.0016 (8)	0.0033 (8)	−0.0048 (8)
C4B	0.0206 (9)	0.0308 (11)	0.0362 (11)	0.0004 (8)	−0.0034 (8)	−0.0133 (9)
C5B	0.0222 (10)	0.0354 (11)	0.0250 (9)	0.0063 (8)	−0.0038 (7)	−0.0070 (8)
C6B	0.0213 (9)	0.0254 (9)	0.0212 (8)	0.0062 (7)	0.0014 (7)	−0.0019 (8)
C7B	0.0353 (11)	0.0253 (10)	0.0283 (10)	−0.0100 (9)	0.0094 (8)	0.0047 (8)
C8B	0.0171 (9)	0.0241 (10)	0.0336 (10)	−0.0039 (7)	0.0027 (7)	0.0009 (8)
C9B	0.0218 (10)	0.0223 (10)	0.0581 (14)	−0.0020 (8)	0.0040 (9)	0.0019 (10)
C10B	0.0218 (10)	0.0288 (11)	0.0657 (16)	−0.0039 (9)	0.0135 (10)	−0.0190 (11)
C11B	0.0229 (10)	0.0411 (12)	0.0403 (11)	−0.0105 (9)	0.0127 (9)	−0.0188 (10)
C12B	0.0175 (9)	0.0341 (11)	0.0264 (9)	−0.0067 (8)	0.0061 (7)	−0.0057 (8)
C13B	0.0117 (8)	0.0243 (9)	0.0241 (9)	−0.0032 (7)	0.0045 (6)	−0.0036 (7)
C14B	0.0169 (9)	0.0228 (9)	0.0163 (8)	0.0010 (7)	0.0014 (6)	0.0015 (7)
C15B	0.0168 (9)	0.0341 (10)	0.0184 (8)	0.0037 (8)	0.0022 (7)	0.0015 (8)
C16B	0.0178 (9)	0.0327 (11)	0.0274 (9)	−0.0008 (8)	0.0048 (7)	0.0102 (8)
C17B	0.0169 (9)	0.0289 (10)	0.0206 (8)	−0.0005 (7)	0.0038 (7)	−0.0008 (7)
C18B	0.0343 (13)	0.079 (2)	0.0434 (13)	−0.0256 (13)	0.0172 (11)	−0.0361 (14)
C19B	0.0280 (12)	0.0747 (19)	0.0382 (12)	−0.0149 (12)	−0.0115 (9)	0.0277 (13)

S1A—C6A	1.7713 (19)	S1B—C6B	1.766 (2)
S1A—C7A	1.822 (2)	S1B—C7B	1.811 (2)
O1A—C14A	1.418 (2)	O1B—C14B	1.412 (2)
O1A—H1A	0.8400	O1B—H1B	0.8400
N1A—C19A	1.463 (3)	N1B—C18B	1.461 (3)
N1A—C18A	1.468 (3)	N1B—C19B	1.465 (3)
N1A—C17A	1.473 (3)	N1B—C17B	1.470 (2)
C1A—C2A	1.398 (3)	C1B—C2B	1.397 (3)
C1A—C6A	1.406 (3)	C1B—C6B	1.408 (2)
C1A—C14A	1.543 (2)	C1B—C14B	1.545 (2)
C2A—C3A	1.393 (3)	C2B—C3B	1.393 (3)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.380 (3)	C3B—C4B	1.388 (3)
C3A—H3AA	0.9500	C3B—H3BA	0.9500
C4A—C5A	1.380 (3)	C4B—C5B	1.375 (3)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.402 (3)	C5B—C6B	1.401 (3)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C7A—C8A	1.498 (3)	C7B—C8B	1.521 (3)
C7A—H7AA	0.9900	C7B—H7BA	0.9900
C7A—H7AB	0.9900	C7B—H7BB	0.9900
C8A—C9A	1.398 (3)	C8B—C13B	1.398 (3)
C8A—C13A	1.408 (3)	C8B—C9B	1.402 (3)
C9A—C10A	1.376 (3)	C9B—C10B	1.384 (4)
C9A—H9AA	0.9500	C9B—H9BA	0.9500
C10A—C11A	1.382 (3)	C10B—C11B	1.373 (4)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.390 (3)	C11B—C12B	1.386 (3)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.390 (3)	C12B—C13B	1.402 (3)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.548 (2)	C13B—C14B	1.552 (3)
C14A—C15A	1.550 (2)	C14B—C15B	1.545 (2)
C15A—C16A	1.540 (2)	C15B—C16B	1.534 (3)
C15A—H15A	0.9900	C15B—H15C	0.9900
C15A—H15B	0.9900	C15B—H15D	0.9900
C16A—C17A	1.525 (3)	C16B—C17B	1.525 (3)
C16A—H16A	0.9900	C16B—H16C	0.9900
C16A—H16B	0.9900	C16B—H16D	0.9900
C17A—H17A	0.9900	C17B—H17C	0.9900
C17A—H17B	0.9900	C17B—H17D	0.9900
C18A—H18A	0.9800	C18B—H18D	0.9800
C18A—H18B	0.9800	C18B—H18E	0.9800
C18A—H18C	0.9800	C18B—H18F	0.9800
C19A—H19A	0.9800	C19B—H19D	0.9800
C19A—H19B	0.9800	C19B—H19E	0.9800
C19A—H19C	0.9800	C19B—H19F	0.9800
C6A—S1A—C7A	109.55 (9)	C6B—S1B—C7B	110.20 (9)
C14A—O1A—H1A	109.5	C14B—O1B—H1B	109.5
C19A—N1A—C18A	109.89 (18)	C18B—N1B—C19B	111.0 (2)
C19A—N1A—C17A	110.88 (17)	C18B—N1B—C17B	111.00 (19)
C18A—N1A—C17A	111.53 (16)	C19B—N1B—C17B	109.77 (18)
C2A—C1A—C6A	117.58 (17)	C2B—C1B—C6B	117.73 (17)
C2A—C1A—C14A	118.41 (17)	C2B—C1B—C14B	118.00 (15)
C6A—C1A—C14A	123.95 (16)	C6B—C1B—C14B	124.27 (17)
C3A—C2A—C1A	122.01 (19)	C3B—C2B—C1B	122.07 (18)
C3A—C2A—H2AA	119.0	C3B—C2B—H2BA	119.0
C1A—C2A—H2AA	119.0	C1B—C2B—H2BA	119.0
C4A—C3A—C2A	120.05 (19)	C4B—C3B—C2B	119.4 (2)
C4A—C3A—H3AA	120.0	C4B—C3B—H3BA	120.3
C2A—C3A—H3AA	120.0	C2B—C3B—H3BA	120.3
C5A—C4A—C3A	118.91 (18)	C5B—C4B—C3B	119.56 (19)
C5A—C4A—H4AA	120.5	C5B—C4B—H4BA	120.2
C3A—C4A—H4AA	120.5	C3B—C4B—H4BA	120.2
C4A—C5A—C6A	121.9 (2)	C4B—C5B—C6B	121.55 (18)
C4A—C5A—H5AA	119.0	C4B—C5B—H5BA	119.2
C6A—C5A—H5AA	119.0	C6B—C5B—H5BA	119.2
C5A—C6A—C1A	119.50 (18)	C5B—C6B—C1B	119.62 (19)
C5A—C6A—S1A	110.96 (15)	C5B—C6B—S1B	111.62 (14)
C1A—C6A—S1A	129.40 (14)	C1B—C6B—S1B	128.64 (16)
C8A—C7A—S1A	115.01 (13)	C8B—C7B—S1B	116.69 (14)
C8A—C7A—H7AA	108.5	C8B—C7B—H7BA	108.1
S1A—C7A—H7AA	108.5	S1B—C7B—H7BA	108.1
C8A—C7A—H7AB	108.5	C8B—C7B—H7BB	108.1
S1A—C7A—H7AB	108.5	S1B—C7B—H7BB	108.1
H7AA—C7A—H7AB	107.5	H7BA—C7B—H7BB	107.3
C9A—C8A—C13A	119.34 (18)	C13B—C8B—C9B	119.4 (2)
C9A—C8A—C7A	117.71 (18)	C13B—C8B—C7B	123.82 (18)
C13A—C8A—C7A	122.93 (16)	C9B—C8B—C7B	116.7 (2)
C10A—C9A—C8A	121.6 (2)	C10B—C9B—C8B	121.4 (2)
C10A—C9A—H9AA	119.2	C10B—C9B—H9BA	119.3
C8A—C9A—H9AA	119.2	C8B—C9B—H9BA	119.3
C9A—C10A—C11A	119.35 (18)	C11B—C10B—C9B	119.3 (2)
C9A—C10A—H10A	120.3	C11B—C10B—H10B	120.3
C11A—C10A—H10A	120.3	C9B—C10B—H10B	120.3
C10A—C11A—C12A	119.9 (2)	C10B—C11B—C12B	120.1 (2)
C10A—C11A—H11A	120.1	C10B—C11B—H11B	120.0
C12A—C11A—H11A	120.1	C12B—C11B—H11B	120.0
C13A—C12A—C11A	121.7 (2)	C11B—C12B—C13B	121.7 (2)
C13A—C12A—H12A	119.2	C11B—C12B—H12B	119.1
C11A—C12A—H12A	119.2	C13B—C12B—H12B	119.1
C12A—C13A—C8A	118.18 (17)	C8B—C13B—C12B	117.96 (18)
C12A—C13A—C14A	117.78 (17)	C8B—C13B—C14B	123.96 (16)
C8A—C13A—C14A	123.85 (16)	C12B—C13B—C14B	117.86 (17)
O1A—C14A—C1A	106.40 (14)	O1B—C14B—C1B	106.49 (15)
O1A—C14A—C13A	109.58 (15)	O1B—C14B—C15B	108.00 (14)
C1A—C14A—C13A	105.90 (14)	C1B—C14B—C15B	110.53 (14)
O1A—C14A—C15A	108.06 (14)	O1B—C14B—C13B	109.25 (14)
C1A—C14A—C15A	110.73 (14)	C1B—C14B—C13B	105.96 (14)
C13A—C14A—C15A	115.78 (14)	C15B—C14B—C13B	116.21 (16)
C16A—C15A—C14A	116.41 (15)	C16B—C15B—C14B	116.08 (16)
C16A—C15A—H15A	108.2	C16B—C15B—H15C	108.3
C14A—C15A—H15A	108.2	C14B—C15B—H15C	108.3
C16A—C15A—H15B	108.2	C16B—C15B—H15D	108.3
C14A—C15A—H15B	108.2	C14B—C15B—H15D	108.3
H15A—C15A—H15B	107.3	H15C—C15B—H15D	107.4
C17A—C16A—C15A	115.75 (16)	C17B—C16B—C15B	116.37 (17)
C17A—C16A—H16A	108.3	C17B—C16B—H16C	108.2
C15A—C16A—H16A	108.3	C15B—C16B—H16C	108.2
C17A—C16A—H16B	108.3	C17B—C16B—H16D	108.2
C15A—C16A—H16B	108.3	C15B—C16B—H16D	108.2
H16A—C16A—H16B	107.4	H16C—C16B—H16D	107.3
N1A—C17A—C16A	113.87 (15)	N1B—C17B—C16B	114.20 (16)
N1A—C17A—H17A	108.8	N1B—C17B—H17C	108.7
C16A—C17A—H17A	108.8	C16B—C17B—H17C	108.7
N1A—C17A—H17B	108.8	N1B—C17B—H17D	108.7
C16A—C17A—H17B	108.8	C16B—C17B—H17D	108.7
H17A—C17A—H17B	107.7	H17C—C17B—H17D	107.6
N1A—C18A—H18A	109.5	N1B—C18B—H18D	109.5
N1A—C18A—H18B	109.5	N1B—C18B—H18E	109.5
H18A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
N1A—C18A—H18C	109.5	N1B—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H18E—C18B—H18F	109.5
N1A—C19A—H19A	109.5	N1B—C19B—H19D	109.5
N1A—C19A—H19B	109.5	N1B—C19B—H19E	109.5
H19A—C19A—H19B	109.5	H19D—C19B—H19E	109.5
N1A—C19A—H19C	109.5	N1B—C19B—H19F	109.5
H19A—C19A—H19C	109.5	H19D—C19B—H19F	109.5
H19B—C19A—H19C	109.5	H19E—C19B—H19F	109.5
C6A—C1A—C2A—C3A	1.2 (3)	C6B—C1B—C2B—C3B	−1.7 (3)
C14A—C1A—C2A—C3A	178.23 (17)	C14B—C1B—C2B—C3B	179.50 (17)
C1A—C2A—C3A—C4A	−1.2 (3)	C1B—C2B—C3B—C4B	0.8 (3)
C2A—C3A—C4A—C5A	−0.2 (3)	C2B—C3B—C4B—C5B	0.6 (3)
C3A—C4A—C5A—C6A	1.6 (3)	C3B—C4B—C5B—C6B	−1.0 (3)
C4A—C5A—C6A—C1A	−1.6 (3)	C4B—C5B—C6B—C1B	0.1 (3)
C4A—C5A—C6A—S1A	174.51 (16)	C4B—C5B—C6B—S1B	−176.25 (16)
C2A—C1A—C6A—C5A	0.2 (3)	C2B—C1B—C6B—C5B	1.2 (3)
C14A—C1A—C6A—C5A	−176.66 (16)	C14B—C1B—C6B—C5B	179.94 (17)
C2A—C1A—C6A—S1A	−175.12 (14)	C2B—C1B—C6B—S1B	176.89 (15)
C14A—C1A—C6A—S1A	8.0 (3)	C14B—C1B—C6B—S1B	−4.4 (3)
C7A—S1A—C6A—C5A	156.28 (14)	C7B—S1B—C6B—C5B	−153.88 (15)
C7A—S1A—C6A—C1A	−28.0 (2)	C7B—S1B—C6B—C1B	30.1 (2)
C6A—S1A—C7A—C8A	−29.24 (17)	C6B—S1B—C7B—C8B	22.7 (2)
S1A—C7A—C8A—C9A	−114.43 (17)	S1B—C7B—C8B—C13B	−63.9 (2)
S1A—C7A—C8A—C13A	67.3 (2)	S1B—C7B—C8B—C9B	118.40 (19)
C13A—C8A—C9A—C10A	1.4 (3)	C13B—C8B—C9B—C10B	−2.9 (3)
C7A—C8A—C9A—C10A	−176.99 (18)	C7B—C8B—C9B—C10B	174.94 (19)
C8A—C9A—C10A—C11A	−0.3 (3)	C8B—C9B—C10B—C11B	0.2 (3)
C9A—C10A—C11A—C12A	−0.6 (3)	C9B—C10B—C11B—C12B	2.2 (3)
C10A—C11A—C12A—C13A	0.3 (3)	C10B—C11B—C12B—C13B	−1.9 (3)
C11A—C12A—C13A—C8A	0.7 (3)	C9B—C8B—C13B—C12B	3.1 (3)
C11A—C12A—C13A—C14A	−174.38 (16)	C7B—C8B—C13B—C12B	−174.58 (17)
C9A—C8A—C13A—C12A	−1.6 (3)	C9B—C8B—C13B—C14B	−171.44 (17)
C7A—C8A—C13A—C12A	176.71 (17)	C7B—C8B—C13B—C14B	10.9 (3)
C9A—C8A—C13A—C14A	173.24 (17)	C11B—C12B—C13B—C8B	−0.7 (3)
C7A—C8A—C13A—C14A	−8.5 (3)	C11B—C12B—C13B—C14B	174.11 (17)
C2A—C1A—C14A—O1A	0.3 (2)	C2B—C1B—C14B—O1B	−1.8 (2)
C6A—C1A—C14A—O1A	177.21 (16)	C6B—C1B—C14B—O1B	179.50 (16)
C2A—C1A—C14A—C13A	−116.21 (17)	C2B—C1B—C14B—C15B	−118.81 (18)
C6A—C1A—C14A—C13A	60.7 (2)	C6B—C1B—C14B—C15B	62.4 (2)
C2A—C1A—C14A—C15A	117.54 (18)	C2B—C1B—C14B—C13B	114.50 (18)
C6A—C1A—C14A—C15A	−65.6 (2)	C6B—C1B—C14B—C13B	−64.2 (2)
C12A—C13A—C14A—O1A	−11.1 (2)	C8B—C13B—C14B—O1B	−176.78 (16)
C8A—C13A—C14A—O1A	174.06 (15)	C12B—C13B—C14B—O1B	8.7 (2)
C12A—C13A—C14A—C1A	103.27 (18)	C8B—C13B—C14B—C1B	68.8 (2)
C8A—C13A—C14A—C1A	−71.5 (2)	C12B—C13B—C14B—C1B	−105.66 (18)
C12A—C13A—C14A—C15A	−133.61 (17)	C8B—C13B—C14B—C15B	−54.3 (2)
C8A—C13A—C14A—C15A	51.6 (2)	C12B—C13B—C14B—C15B	131.16 (17)
O1A—C14A—C15A—C16A	−76.66 (19)	O1B—C14B—C15B—C16B	72.5 (2)
C1A—C14A—C15A—C16A	167.18 (15)	C1B—C14B—C15B—C16B	−171.34 (16)
C13A—C14A—C15A—C16A	46.6 (2)	C13B—C14B—C15B—C16B	−50.6 (2)
C14A—C15A—C16A—C17A	81.9 (2)	C14B—C15B—C16B—C17B	−84.3 (2)
C19A—N1A—C17A—C16A	161.24 (17)	C18B—N1B—C17B—C16B	73.7 (2)
C18A—N1A—C17A—C16A	−75.9 (2)	C19B—N1B—C17B—C16B	−163.21 (19)
C15A—C16A—C17A—N1A	−66.7 (2)	C15B—C16B—C17B—N1B	67.5 (2)

Cg1, Cg2, Cg7 and Cg8 are the centroids of the C1A—C6A, C8A—C13A, C1B–C6B and C8B—C13B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···N1A	0.84	1.86	2.693 (2)	170
O1B—H1B···N1B	0.84	1.84	2.679 (2)	174
C4A—H4AA···O1B	0.95	2.51	3.253 (2)	135
C3A—H3AA···Cg7i	0.95	2.74	3.526 (6)	140
C17A—H17A···Cg1ii	0.99	2.67	3.537 (7)	147
C17A—H17B···Cg2ii	0.99	2.75	3.720 (3)	167
C17B—H17C···Cg8iii	0.99	2.68	3.663 (6)	170
C17B—17D···Cg7iii	0.99	2.64	3.538 (1)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯N1A	0.84	1.86	2.693 (2)	170
O1B—H1B⋯N1B	0.84	1.84	2.679 (2)	174
C4A—H4AA⋯O1B	0.95	2.51	3.253 (2)	135
C3A—H3AA⋯Cg7i	0.95	2.74	3.526 (6)	140
C17A—H17A⋯Cg1ii	0.99	2.67	3.537 (7)	147
C17A—H17B⋯Cg2ii	0.99	2.75	3.720 (3)	167
C17B—H17C⋯Cg8iii	0.99	2.68	3.663 (6)	170
C17B—17D⋯Cg7iii	0.99	2.64	3.538 (1)	149

Symmetry codes: (i) ; (ii) ; (iii) . Cg1, Cg2, Cg7 and Cg8 are the centroids of the C1A—C6A, C8A—C13A, C1B–C6B and C8B—C13B rings, respectively.