1-(1-Hydr-oxy-9H-carbazol-2-yl)-3-methyl-but-2-en-1-one.

The title compound, C(17)H(15)NO(2), was prepared as one of two products of the AlCl(3)/POCl(3)-catalysed reaction of 9-carbazol-1-ol with 3,3-dimethyacrylic acid. It crystallizes with two crystallographically independent mol-ecules, A and B, which are virtually superimposable but not related by any translational or other pseudosymmetry. Both independent mol-ecules are almost planar [r.m.s. deviations from planarity = 0.053 (1) and 0.079 (1) Å in A and B, respectively] and contain an intramolecular O-H⋯O hydrogen bond. Each type of mol-ecules is connected via pairs of N-H⋯O hydrogen bonds, forming centrosymmetric A(2) and B(2) dimers which are, in turn, arranged in offset π-stacks extending along the a-axis direction. The offset of the dimers and the tilt angle of the mol-ecules allows the formation of alternating C-H⋯π inter-actions between A and B mol-ecules of parallel stacks.

Related literature

For synthetic strategies for the synthesis of carbazole and its derivatives, see: Chakraborty (1993 ▶). For the isolation of pyran­ocarbazoles from various plant species, see: Knölker & Reddy (2002 ▶, and references therein). For the synthesis of related compounds, see: Kavitha & Rajendra Prasad (2003a ▶,b ▶); Patel (1982 ▶). For the structure of the second product of the reaction yielding the title compound, see: Sridharan et al. (2008 ▶).

Experimental

Crystal data

C17H15NO2

M = 265.30

Triclinic,

a = 6.3416 (9) Å

b = 15.202 (2) Å

c = 15.462 (3) Å

α = 115.216 (5)°

β = 95.042 (5)°

γ = 101.922 (4)°

V = 1293.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.31 × 0.19 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (APEX2; Bruker, 2007 ▶) T min = 0.749, T max = 0.986

13387 measured reflections

6364 independent reflections

4788 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.123

S = 1.01

6364 reflections

367 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 ▶) and publCIF (McMahon & Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810000322/bv2136sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000322/bv2136Isup2.hkl

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

C17H15NO2	Z = 4
Mr = 265.30	F(000) = 560
Triclinic, P1	Dx = 1.363 Mg m−3
Hall symbol: -P 1	Melting point: 483 K
a = 6.3416 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.202 (2) Å	Cell parameters from 3373 reflections
c = 15.462 (3) Å	θ = 2.7–29.0°
α = 115.216 (5)°	µ = 0.09 mm−1
β = 95.042 (5)°	T = 100 K
γ = 101.922 (4)°	Plate, orange
V = 1293.2 (4) Å3	0.31 × 0.19 × 0.16 mm

Bruker SMART APEX CCD diffractometer	6364 independent reflections
Radiation source: fine-focus sealed tube	4788 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan (APEX2; Bruker, 2007)	h = −8→8
Tmin = 0.749, Tmax = 0.986	k = −20→20
13387 measured reflections	l = −20→20

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0531P)2 + 0.5261P] where P = (Fo2 + 2Fc2)/3
6364 reflections	(Δ/σ)max < 0.001
367 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.25 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
C1A	0.7818 (2)	0.24361 (12)	0.56142 (11)	0.0177 (3)
C2A	0.6819 (3)	0.31619 (12)	0.61788 (11)	0.0198 (3)
H2A	0.5434	0.2975	0.6334	0.024*
C3A	0.7926 (3)	0.41613 (12)	0.65017 (12)	0.0220 (3)
H3A	0.7278	0.4672	0.6882	0.026*
C4A	0.9985 (3)	0.44455 (12)	0.62833 (12)	0.0224 (3)
H4A	1.0709	0.5141	0.6522	0.027*
C5A	1.0970 (3)	0.37214 (12)	0.57234 (11)	0.0206 (3)
H5A	1.2366	0.3916	0.5580	0.025*
C6A	0.9881 (2)	0.26989 (12)	0.53716 (11)	0.0175 (3)
C7A	0.8360 (2)	−0.00303 (12)	0.40772 (11)	0.0164 (3)
C8A	0.8533 (2)	0.09890 (12)	0.46513 (11)	0.0165 (3)
C9A	1.0325 (2)	0.17577 (11)	0.47439 (11)	0.0164 (3)
C10A	1.2026 (2)	0.15003 (12)	0.42390 (11)	0.0179 (3)
H10A	1.3252	0.2011	0.4289	0.021*
C11A	1.1880 (2)	0.04945 (12)	0.36717 (11)	0.0177 (3)
H11A	1.3029	0.0321	0.3334	0.021*
C12A	1.0068 (2)	−0.02914 (11)	0.35748 (11)	0.0164 (3)
C13A	0.9842 (2)	−0.13732 (12)	0.29741 (11)	0.0181 (3)
C14A	1.1542 (3)	−0.17222 (12)	0.24376 (11)	0.0190 (3)
H14A	1.2805	−0.1225	0.2493	0.023*
C15A	1.1436 (3)	−0.26979 (12)	0.18718 (11)	0.0201 (3)
C16A	0.9526 (3)	−0.35834 (12)	0.16533 (12)	0.0238 (3)
H16A	0.9365	−0.3639	0.2254	0.036*
H16B	0.9790	−0.4204	0.1171	0.036*
H16C	0.8178	−0.3485	0.1392	0.036*
C17A	1.3362 (3)	−0.29673 (13)	0.14197 (12)	0.0237 (3)
H17A	1.4516	−0.2348	0.1590	0.036*
H17B	1.2888	−0.3343	0.0709	0.036*
H17C	1.3937	−0.3386	0.1665	0.036*
C1B	0.6941 (2)	−0.19517 (12)	0.77600 (11)	0.0178 (3)
C2B	0.7881 (3)	−0.27530 (12)	0.73361 (11)	0.0205 (3)
H2B	0.9299	−0.2729	0.7617	0.025*
C3B	0.6655 (3)	−0.35811 (12)	0.64911 (12)	0.0224 (3)
H3B	0.7260	−0.4132	0.6179	0.027*
C4B	0.4536 (3)	−0.36301 (12)	0.60808 (12)	0.0218 (3)
H4B	0.3725	−0.4217	0.5508	0.026*
C5B	0.3619 (3)	−0.28337 (12)	0.65017 (11)	0.0197 (3)
H5B	0.2188	−0.2870	0.6223	0.024*
C6B	0.4834 (2)	−0.19745 (12)	0.73445 (11)	0.0171 (3)
C7B	0.6547 (2)	0.05079 (11)	0.94208 (11)	0.0168 (3)
C8B	0.6330 (2)	−0.04659 (11)	0.86929 (11)	0.0169 (3)
C9B	0.4459 (2)	−0.10097 (11)	0.79421 (11)	0.0163 (3)
C10B	0.2753 (2)	−0.05548 (12)	0.79034 (11)	0.0180 (3)
H10B	0.1488	−0.0906	0.7394	0.022*
C11B	0.2948 (2)	0.04032 (12)	0.86139 (11)	0.0181 (3)
H11B	0.1798	0.0710	0.8586	0.022*
C12B	0.4818 (2)	0.09561 (11)	0.93938 (11)	0.0168 (3)
C13B	0.5056 (2)	0.19747 (12)	1.01756 (11)	0.0182 (3)
C14B	0.3307 (2)	0.24795 (12)	1.02043 (11)	0.0192 (3)
H14B	0.1949	0.2088	0.9761	0.023*
C15B	0.3472 (3)	0.34515 (12)	1.08080 (12)	0.0205 (3)
C16B	0.5470 (3)	0.41995 (13)	1.15485 (13)	0.0277 (4)
H16D	0.5608	0.4072	1.2118	0.042*
H16E	0.5326	0.4885	1.1750	0.042*
H16F	0.6781	0.4130	1.1262	0.042*
C17B	0.1508 (3)	0.38542 (13)	1.07778 (13)	0.0267 (4)
H17D	0.0296	0.3324	1.0266	0.040*
H17E	0.1892	0.4432	1.0637	0.040*
H17F	0.1055	0.4070	1.1410	0.040*
N1A	0.7042 (2)	0.13977 (10)	0.51833 (9)	0.0180 (3)
H1A	0.5806	0.1055	0.5239	0.022*
N1B	0.7808 (2)	−0.10416 (10)	0.85829 (9)	0.0182 (3)
H1B	0.9085	−0.0858	0.8972	0.022*
O1A	0.65515 (17)	−0.07178 (8)	0.40157 (8)	0.0203 (2)
H1C	0.6662	−0.1302	0.3672	0.030*
O2A	0.81641 (18)	−0.20127 (8)	0.29274 (8)	0.0235 (3)
O1B	0.83971 (17)	0.09766 (8)	1.01146 (8)	0.0207 (2)
H1D	0.8316	0.1547	1.0516	0.031*
O2B	0.67656 (18)	0.24120 (8)	1.08281 (8)	0.0233 (3)

	U11	U22	U33	U12	U13	U23
C1A	0.0170 (7)	0.0206 (8)	0.0164 (7)	0.0041 (6)	0.0024 (6)	0.0099 (6)
C2A	0.0189 (7)	0.0237 (8)	0.0185 (8)	0.0080 (6)	0.0058 (6)	0.0097 (7)
C3A	0.0249 (8)	0.0231 (8)	0.0192 (8)	0.0095 (7)	0.0050 (6)	0.0093 (7)
C4A	0.0245 (8)	0.0185 (8)	0.0237 (8)	0.0043 (6)	0.0023 (6)	0.0103 (7)
C5A	0.0184 (7)	0.0236 (8)	0.0207 (8)	0.0043 (6)	0.0033 (6)	0.0115 (7)
C6A	0.0170 (7)	0.0210 (8)	0.0166 (7)	0.0059 (6)	0.0031 (6)	0.0103 (6)
C7A	0.0139 (7)	0.0206 (8)	0.0159 (7)	0.0037 (6)	0.0027 (6)	0.0100 (6)
C8A	0.0149 (7)	0.0214 (8)	0.0153 (7)	0.0059 (6)	0.0034 (6)	0.0097 (6)
C9A	0.0155 (7)	0.0205 (8)	0.0149 (7)	0.0039 (6)	0.0015 (6)	0.0102 (6)
C10A	0.0153 (7)	0.0210 (8)	0.0192 (8)	0.0032 (6)	0.0036 (6)	0.0117 (6)
C11A	0.0149 (7)	0.0228 (8)	0.0183 (7)	0.0060 (6)	0.0056 (6)	0.0112 (6)
C12A	0.0156 (7)	0.0204 (8)	0.0152 (7)	0.0056 (6)	0.0028 (6)	0.0097 (6)
C13A	0.0168 (7)	0.0213 (8)	0.0172 (7)	0.0045 (6)	0.0025 (6)	0.0101 (6)
C14A	0.0176 (7)	0.0213 (8)	0.0197 (8)	0.0058 (6)	0.0052 (6)	0.0101 (7)
C15A	0.0201 (7)	0.0252 (8)	0.0181 (8)	0.0082 (6)	0.0040 (6)	0.0117 (7)
C16A	0.0226 (8)	0.0212 (8)	0.0264 (9)	0.0071 (6)	0.0061 (7)	0.0088 (7)
C17A	0.0218 (8)	0.0263 (9)	0.0233 (8)	0.0096 (7)	0.0065 (6)	0.0098 (7)
C1B	0.0183 (7)	0.0198 (8)	0.0167 (7)	0.0043 (6)	0.0047 (6)	0.0097 (6)
C2B	0.0215 (8)	0.0223 (8)	0.0208 (8)	0.0077 (6)	0.0059 (6)	0.0114 (7)
C3B	0.0302 (9)	0.0203 (8)	0.0210 (8)	0.0097 (7)	0.0098 (7)	0.0111 (7)
C4B	0.0268 (8)	0.0187 (8)	0.0167 (8)	0.0022 (6)	0.0041 (6)	0.0071 (6)
C5B	0.0191 (7)	0.0232 (8)	0.0174 (7)	0.0033 (6)	0.0038 (6)	0.0107 (7)
C6B	0.0168 (7)	0.0194 (8)	0.0175 (7)	0.0050 (6)	0.0057 (6)	0.0103 (6)
C7B	0.0151 (7)	0.0200 (8)	0.0151 (7)	0.0031 (6)	0.0016 (6)	0.0090 (6)
C8B	0.0154 (7)	0.0201 (8)	0.0177 (7)	0.0054 (6)	0.0041 (6)	0.0104 (6)
C9B	0.0164 (7)	0.0184 (7)	0.0145 (7)	0.0028 (6)	0.0043 (6)	0.0083 (6)
C10B	0.0148 (7)	0.0226 (8)	0.0173 (7)	0.0040 (6)	0.0014 (6)	0.0106 (6)
C11B	0.0157 (7)	0.0216 (8)	0.0194 (8)	0.0068 (6)	0.0028 (6)	0.0109 (6)
C12B	0.0171 (7)	0.0187 (8)	0.0168 (7)	0.0054 (6)	0.0047 (6)	0.0098 (6)
C13B	0.0186 (7)	0.0196 (8)	0.0179 (7)	0.0049 (6)	0.0050 (6)	0.0097 (6)
C14B	0.0169 (7)	0.0223 (8)	0.0184 (8)	0.0055 (6)	0.0026 (6)	0.0093 (7)
C15B	0.0205 (8)	0.0233 (8)	0.0208 (8)	0.0071 (6)	0.0080 (6)	0.0116 (7)
C16B	0.0222 (8)	0.0213 (9)	0.0325 (10)	0.0055 (7)	0.0056 (7)	0.0060 (8)
C17B	0.0264 (9)	0.0265 (9)	0.0246 (9)	0.0128 (7)	0.0041 (7)	0.0071 (7)
N1A	0.0156 (6)	0.0186 (6)	0.0200 (7)	0.0046 (5)	0.0070 (5)	0.0085 (5)
N1B	0.0145 (6)	0.0198 (7)	0.0187 (6)	0.0060 (5)	0.0013 (5)	0.0071 (5)
O1A	0.0173 (5)	0.0181 (5)	0.0243 (6)	0.0028 (4)	0.0085 (4)	0.0087 (5)
O2A	0.0206 (6)	0.0208 (6)	0.0263 (6)	0.0032 (5)	0.0082 (5)	0.0085 (5)
O1B	0.0179 (5)	0.0194 (6)	0.0194 (6)	0.0052 (4)	−0.0021 (4)	0.0048 (5)
O2B	0.0209 (6)	0.0205 (6)	0.0226 (6)	0.0048 (5)	−0.0020 (5)	0.0060 (5)

C1A—N1A	1.380 (2)	C1B—C6B	1.418 (2)
C1A—C2A	1.395 (2)	C2B—C3B	1.383 (2)
C1A—C6A	1.418 (2)	C2B—H2B	0.9500
C2A—C3A	1.379 (2)	C3B—C4B	1.408 (2)
C2A—H2A	0.9500	C3B—H3B	0.9500
C3A—C4A	1.406 (2)	C4B—C5B	1.383 (2)
C3A—H3A	0.9500	C4B—H4B	0.9500
C4A—C5A	1.385 (2)	C5B—C6B	1.398 (2)
C4A—H4A	0.9500	C5B—H5B	0.9500
C5A—C6A	1.400 (2)	C6B—C9B	1.446 (2)
C5A—H5A	0.9500	C7B—O1B	1.3478 (17)
C6A—C9A	1.449 (2)	C7B—C8B	1.395 (2)
C7A—O1A	1.3479 (17)	C7B—C12B	1.412 (2)
C7A—C8A	1.393 (2)	C8B—N1B	1.3833 (19)
C7A—C12A	1.414 (2)	C8B—C9B	1.405 (2)
C8A—N1A	1.3786 (19)	C9B—C10B	1.409 (2)
C8A—C9A	1.399 (2)	C10B—C11B	1.372 (2)
C9A—C10A	1.410 (2)	C10B—H10B	0.9500
C10A—C11A	1.378 (2)	C11B—C12B	1.428 (2)
C10A—H10A	0.9500	C11B—H11B	0.9500
C11A—C12A	1.421 (2)	C12B—C13B	1.469 (2)
C11A—H11A	0.9500	C13B—O2B	1.2545 (19)
C12A—C13A	1.472 (2)	C13B—C14B	1.467 (2)
C13A—O2A	1.2577 (18)	C14B—C15B	1.345 (2)
C13A—C14A	1.466 (2)	C14B—H14B	0.9500
C14A—C15A	1.347 (2)	C15B—C16B	1.500 (2)
C14A—H14A	0.9500	C15B—C17B	1.502 (2)
C15A—C17A	1.503 (2)	C16B—H16D	0.9800
C15A—C16A	1.504 (2)	C16B—H16E	0.9800
C16A—H16A	0.9800	C16B—H16F	0.9800
C16A—H16B	0.9800	C17B—H17D	0.9800
C16A—H16C	0.9800	C17B—H17E	0.9800
C17A—H17A	0.9800	C17B—H17F	0.9800
C17A—H17B	0.9800	N1A—H1A	0.8800
C17A—H17C	0.9800	N1B—H1B	0.8800
C1B—N1B	1.378 (2)	O1A—H1C	0.8400
C1B—C2B	1.399 (2)	O1B—H1D	0.8400
N1A—C1A—C2A	128.77 (14)	C3B—C2B—H2B	121.5
N1A—C1A—C6A	108.97 (13)	C1B—C2B—H2B	121.5
C2A—C1A—C6A	122.23 (14)	C2B—C3B—C4B	121.82 (15)
C3A—C2A—C1A	117.24 (15)	C2B—C3B—H3B	119.1
C3A—C2A—H2A	121.4	C4B—C3B—H3B	119.1
C1A—C2A—H2A	121.4	C5B—C4B—C3B	120.82 (15)
C2A—C3A—C4A	121.82 (15)	C5B—C4B—H4B	119.6
C2A—C3A—H3A	119.1	C3B—C4B—H4B	119.6
C4A—C3A—H3A	119.1	C4B—C5B—C6B	118.86 (15)
C5A—C4A—C3A	120.66 (15)	C4B—C5B—H5B	120.6
C5A—C4A—H4A	119.7	C6B—C5B—H5B	120.6
C3A—C4A—H4A	119.7	C5B—C6B—C1B	119.39 (14)
C4A—C5A—C6A	119.11 (15)	C5B—C6B—C9B	133.95 (14)
C4A—C5A—H5A	120.4	C1B—C6B—C9B	106.65 (13)
C6A—C5A—H5A	120.4	O1B—C7B—C8B	118.52 (13)
C5A—C6A—C1A	118.91 (14)	O1B—C7B—C12B	123.14 (14)
C5A—C6A—C9A	134.61 (14)	C8B—C7B—C12B	118.34 (13)
C1A—C6A—C9A	106.44 (13)	N1B—C8B—C7B	127.82 (14)
O1A—C7A—C8A	118.30 (13)	N1B—C8B—C9B	109.87 (13)
O1A—C7A—C12A	123.26 (14)	C7B—C8B—C9B	122.31 (14)
C8A—C7A—C12A	118.43 (13)	C8B—C9B—C10B	119.36 (14)
N1A—C8A—C7A	127.35 (14)	C8B—C9B—C6B	106.02 (13)
N1A—C8A—C9A	110.20 (13)	C10B—C9B—C6B	134.60 (14)
C7A—C8A—C9A	122.44 (14)	C11B—C10B—C9B	118.89 (14)
C8A—C9A—C10A	119.29 (14)	C11B—C10B—H10B	120.6
C8A—C9A—C6A	106.02 (13)	C9B—C10B—H10B	120.6
C10A—C9A—C6A	134.66 (14)	C10B—C11B—C12B	122.35 (14)
C11A—C10A—C9A	118.85 (14)	C10B—C11B—H11B	118.8
C11A—C10A—H10A	120.6	C12B—C11B—H11B	118.8
C9A—C10A—H10A	120.6	C7B—C12B—C11B	118.72 (14)
C10A—C11A—C12A	122.25 (14)	C7B—C12B—C13B	117.64 (13)
C10A—C11A—H11A	118.9	C11B—C12B—C13B	123.64 (14)
C12A—C11A—H11A	118.9	O2B—C13B—C14B	119.83 (14)
C7A—C12A—C11A	118.74 (14)	O2B—C13B—C12B	119.54 (14)
C7A—C12A—C13A	117.25 (13)	C14B—C13B—C12B	120.63 (14)
C11A—C12A—C13A	124.01 (14)	C15B—C14B—C13B	125.25 (15)
O2A—C13A—C14A	119.28 (14)	C15B—C14B—H14B	117.4
O2A—C13A—C12A	119.28 (14)	C13B—C14B—H14B	117.4
C14A—C13A—C12A	121.43 (13)	C14B—C15B—C16B	125.88 (15)
C15A—C14A—C13A	124.55 (14)	C14B—C15B—C17B	119.22 (15)
C15A—C14A—H14A	117.7	C16B—C15B—C17B	114.89 (14)
C13A—C14A—H14A	117.7	C15B—C16B—H16D	109.5
C14A—C15A—C17A	119.65 (15)	C15B—C16B—H16E	109.5
C14A—C15A—C16A	125.41 (15)	H16D—C16B—H16E	109.5
C17A—C15A—C16A	114.93 (14)	C15B—C16B—H16F	109.5
C15A—C16A—H16A	109.5	H16D—C16B—H16F	109.5
C15A—C16A—H16B	109.5	H16E—C16B—H16F	109.5
H16A—C16A—H16B	109.5	C15B—C17B—H17D	109.5
C15A—C16A—H16C	109.5	C15B—C17B—H17E	109.5
H16A—C16A—H16C	109.5	H17D—C17B—H17E	109.5
H16B—C16A—H16C	109.5	C15B—C17B—H17F	109.5
C15A—C17A—H17A	109.5	H17D—C17B—H17F	109.5
C15A—C17A—H17B	109.5	H17E—C17B—H17F	109.5
H17A—C17A—H17B	109.5	C8A—N1A—C1A	108.35 (12)
C15A—C17A—H17C	109.5	C8A—N1A—H1A	125.8
H17A—C17A—H17C	109.5	C1A—N1A—H1A	125.8
H17B—C17A—H17C	109.5	C1B—N1B—C8B	108.43 (12)
N1B—C1B—C2B	128.95 (14)	C1B—N1B—H1B	125.8
N1B—C1B—C6B	109.01 (13)	C8B—N1B—H1B	125.8
C2B—C1B—C6B	122.02 (14)	C7A—O1A—H1C	109.5
C3B—C2B—C1B	117.05 (15)	C7B—O1B—H1D	109.5
N1A—C1A—C2A—C3A	−178.05 (15)	C3B—C4B—C5B—C6B	0.0 (2)
C6A—C1A—C2A—C3A	−0.2 (2)	C4B—C5B—C6B—C1B	−1.7 (2)
C1A—C2A—C3A—C4A	−0.6 (2)	C4B—C5B—C6B—C9B	176.91 (15)
C2A—C3A—C4A—C5A	0.5 (2)	N1B—C1B—C6B—C5B	−179.42 (13)
C3A—C4A—C5A—C6A	0.3 (2)	C2B—C1B—C6B—C5B	2.0 (2)
C4A—C5A—C6A—C1A	−1.1 (2)	N1B—C1B—C6B—C9B	1.62 (16)
C4A—C5A—C6A—C9A	176.35 (16)	C2B—C1B—C6B—C9B	−176.96 (14)
N1A—C1A—C6A—C5A	179.28 (13)	O1B—C7B—C8B—N1B	0.3 (2)
C2A—C1A—C6A—C5A	1.1 (2)	C12B—C7B—C8B—N1B	−179.84 (14)
N1A—C1A—C6A—C9A	1.17 (16)	O1B—C7B—C8B—C9B	180.00 (13)
C2A—C1A—C6A—C9A	−177.06 (14)	C12B—C7B—C8B—C9B	−0.1 (2)
O1A—C7A—C8A—N1A	0.1 (2)	N1B—C8B—C9B—C10B	−178.81 (13)
C12A—C7A—C8A—N1A	178.99 (14)	C7B—C8B—C9B—C10B	1.4 (2)
O1A—C7A—C8A—C9A	−178.67 (13)	N1B—C8B—C9B—C6B	0.17 (17)
C12A—C7A—C8A—C9A	0.2 (2)	C7B—C8B—C9B—C6B	−179.61 (13)
N1A—C8A—C9A—C10A	−178.80 (13)	C5B—C6B—C9B—C8B	−179.81 (16)
C7A—C8A—C9A—C10A	0.2 (2)	C1B—C6B—C9B—C8B	−1.08 (16)
N1A—C8A—C9A—C6A	−0.38 (16)	C5B—C6B—C9B—C10B	−1.1 (3)
C7A—C8A—C9A—C6A	178.57 (13)	C1B—C6B—C9B—C10B	177.67 (16)
C5A—C6A—C9A—C8A	−178.16 (16)	C8B—C9B—C10B—C11B	−1.3 (2)
C1A—C6A—C9A—C8A	−0.48 (16)	C6B—C9B—C10B—C11B	−179.88 (15)
C5A—C6A—C9A—C10A	−0.1 (3)	C9B—C10B—C11B—C12B	−0.2 (2)
C1A—C6A—C9A—C10A	177.58 (16)	O1B—C7B—C12B—C11B	178.60 (14)
C8A—C9A—C10A—C11A	−0.4 (2)	C8B—C7B—C12B—C11B	−1.3 (2)
C6A—C9A—C10A—C11A	−178.27 (15)	O1B—C7B—C12B—C13B	−1.2 (2)
C9A—C10A—C11A—C12A	0.3 (2)	C8B—C7B—C12B—C13B	178.92 (13)
O1A—C7A—C12A—C11A	178.50 (13)	C10B—C11B—C12B—C7B	1.5 (2)
C8A—C7A—C12A—C11A	−0.3 (2)	C10B—C11B—C12B—C13B	−178.77 (14)
O1A—C7A—C12A—C13A	−1.2 (2)	C7B—C12B—C13B—O2B	0.6 (2)
C8A—C7A—C12A—C13A	180.00 (13)	C11B—C12B—C13B—O2B	−179.21 (14)
C10A—C11A—C12A—C7A	0.1 (2)	C7B—C12B—C13B—C14B	−178.87 (14)
C10A—C11A—C12A—C13A	179.72 (14)	C11B—C12B—C13B—C14B	1.4 (2)
C7A—C12A—C13A—O2A	0.3 (2)	O2B—C13B—C14B—C15B	9.6 (2)
C11A—C12A—C13A—O2A	−179.31 (14)	C12B—C13B—C14B—C15B	−170.95 (15)
C7A—C12A—C13A—C14A	−178.98 (13)	C13B—C14B—C15B—C16B	1.0 (3)
C11A—C12A—C13A—C14A	1.4 (2)	C13B—C14B—C15B—C17B	−177.81 (15)
O2A—C13A—C14A—C15A	1.0 (2)	C7A—C8A—N1A—C1A	−177.76 (14)
C12A—C13A—C14A—C15A	−179.66 (15)	C9A—C8A—N1A—C1A	1.12 (17)
C13A—C14A—C15A—C17A	−175.27 (14)	C2A—C1A—N1A—C8A	176.66 (15)
C13A—C14A—C15A—C16A	3.4 (3)	C6A—C1A—N1A—C8A	−1.42 (16)
N1B—C1B—C2B—C3B	−178.80 (15)	C2B—C1B—N1B—C8B	176.92 (15)
C6B—C1B—C2B—C3B	−0.5 (2)	C6B—C1B—N1B—C8B	−1.54 (17)
C1B—C2B—C3B—C4B	−1.2 (2)	C7B—C8B—N1B—C1B	−179.39 (14)
C2B—C3B—C4B—C5B	1.5 (2)	C9B—C8B—N1B—C1B	0.85 (17)

Cg1, Cg2 and Cg3 are the centroids of the phenyl rings C1B–C6B, C7A–C12A and C1A–C6A, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1D···O2B	0.84	1.73	2.4762 (16)	146
O1A—H1C···O2A	0.84	1.72	2.4626 (16)	146
N1B—H1B···O1Bi	0.88	2.12	2.9561 (17)	157
N1A—H1A···O1Aii	0.88	2.08	2.8996 (16)	155
C10A—H10A···Cg1iii	0.95	2.66	3.365 (2)	132
C10B—H10B···Cg2ii	0.95	2.68	3.427 (2)	136
C16A—H16A···Cg3iii	0.95	2.77	3.659 (2)	152
C16B—H16D···Cg1iv	0.95	2.96	3.846 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the phenyl rings C1B–C6B, C7A–C12A and C1A–C6A, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1B—H1D⋯O2B	0.84	1.73	2.4762 (16)	146
O1A—H1C⋯O2A	0.84	1.72	2.4626 (16)	146
N1B—H1B⋯O1Bi	0.88	2.12	2.9561 (17)	157
N1A—H1A⋯O1Aii	0.88	2.08	2.8996 (16)	155
C10A—H10A⋯Cg1iii	0.95	2.66	3.365 (2)	132
C10B—H10B⋯Cg2ii	0.95	2.68	3.427 (2)	136
C16A—H16A⋯Cg3iii	0.95	2.77	3.659 (2)	152
C16B—H16D⋯Cg1iv	0.95	2.96	3.846 (2)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .