2-Bromo-5,7-dimeth-oxy-4-phenyl-quinoline.

The title compound, C(17)H(14)BrNO(2), was synthesized by the treatment of 5,7-dimeth-oxy-4-phenyl-quinolin-2-one with phosphoryl bromide in a Vilsmeier-type reaction. There are two independent mol-ecules (A and B) in the asymmetric unit which differ by 11.2° in the orientation of the 4-phenyl ring with respect to the planar quinoline ring system [dihedral angles = 55.15 (8) and 66.34 (8)° in mol-ecules A and B, respectively]. In the crystal structure, the independent mol-ecules are linked via C-H⋯N and C-H⋯O hydrogen bonds, forming centrosymmetric tetra-meric units which are cross-linked through C-H⋯π and C-Br⋯π inter-actions with Br⋯centroid distances of 3.4289 (8) and 3.5967 (8) Å.

Related literature

For a study of the anti­tumor activity of some 5,7-dimethoxy­quinolinlone analogues, see: Joseph et al. (2002 ▶).

Experimental

Crystal data

C17H14BrNO2

M = 344.20

Triclinic,

a = 9.7698 (2) Å

b = 9.9799 (3) Å

c = 14.8076 (4) Å

α = 93.499 (1)°

β = 95.154 (1)°

γ = 91.838 (1)°

V = 1434.22 (7) Å3

Z = 4

Mo Kα radiation

μ = 2.87 mm−1

T = 150 K

0.39 × 0.19 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.401, T max = 0.626

27207 measured reflections

5008 independent reflections

4648 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.100

S = 0.87

5008 reflections

491 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900587X/ci2767sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900587X/ci2767Isup2.hkl

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

C17H14BrNO2	Z = 4
Mr = 344.20	F(000) = 696
Triclinic, P1	Dx = 1.594 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7698 (2) Å	Cell parameters from 9202 reflections
b = 9.9799 (3) Å	θ = 2.4–28.0°
c = 14.8076 (4) Å	µ = 2.87 mm−1
α = 93.499 (1)°	T = 150 K
β = 95.154 (1)°	Needle, light yellow
γ = 91.838 (1)°	0.39 × 0.19 × 0.18 mm
V = 1434.22 (7) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	5008 independent reflections
Radiation source: fine-focus sealed tube	4648 reflections with I > 2σ(I)
graphite	Rint = 0.060
φ scans, and ω scans with κ offsets	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −11→11
Tmin = 0.401, Tmax = 0.626	k = −11→11
27207 measured reflections	l = −17→17

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
5008 reflections	(Δ/σ)max = 0.002
491 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.55 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
Br1A	−0.09830 (2)	0.72553 (2)	0.551387 (13)	0.02782 (11)
N1A	0.06082 (17)	0.81444 (17)	0.42221 (11)	0.0205 (4)
C2A	−0.0207 (2)	0.7146 (2)	0.43692 (13)	0.0202 (4)
C3A	−0.0501 (2)	0.5984 (2)	0.38082 (14)	0.0223 (4)
C4A	0.01131 (19)	0.5845 (2)	0.29994 (13)	0.0185 (4)
C5A	0.15706 (19)	0.70379 (19)	0.19273 (13)	0.0176 (4)
C6A	0.24532 (19)	0.8091 (2)	0.18021 (13)	0.0182 (4)
C7A	0.27300 (19)	0.91362 (19)	0.24867 (13)	0.0197 (4)
C8A	0.2096 (2)	0.9153 (2)	0.32701 (13)	0.0204 (4)
C9A	0.11985 (19)	0.80637 (19)	0.34132 (13)	0.0186 (4)
C10A	0.09499 (19)	0.69426 (19)	0.27681 (13)	0.0178 (4)
C11A	−0.0078 (2)	0.4498 (2)	0.25100 (13)	0.0190 (4)
C12A	−0.1389 (2)	0.3890 (2)	0.23443 (13)	0.0220 (4)
C13A	−0.1566 (2)	0.2565 (2)	0.20000 (15)	0.0265 (5)
C14A	−0.0440 (2)	0.1825 (2)	0.18294 (14)	0.0265 (5)
C15A	0.0871 (2)	0.2423 (2)	0.19786 (13)	0.0236 (4)
C16A	0.1057 (2)	0.3744 (2)	0.23107 (13)	0.0196 (4)
C17A	0.1870 (2)	0.6020 (3)	0.04572 (15)	0.0267 (5)
C18A	0.4127 (2)	1.1078 (2)	0.29986 (15)	0.0262 (5)
O1A	0.11992 (14)	0.60380 (14)	0.12739 (9)	0.0216 (3)
O2A	0.36495 (15)	1.01016 (14)	0.22783 (10)	0.0231 (3)
Br1B	0.55112 (2)	0.694767 (19)	0.898615 (13)	0.02541 (11)
N1B	0.54825 (17)	0.51735 (17)	0.74864 (11)	0.0187 (4)
C2B	0.50047 (19)	0.53079 (19)	0.82786 (13)	0.0183 (4)
C3B	0.4198 (2)	0.4360 (2)	0.86636 (14)	0.0191 (4)
C4B	0.38014 (19)	0.3180 (2)	0.81667 (13)	0.0169 (4)
C5B	0.37631 (19)	0.19046 (19)	0.66232 (13)	0.0183 (4)
C6B	0.4281 (2)	0.1790 (2)	0.57944 (14)	0.0205 (4)
C7B	0.5251 (2)	0.2767 (2)	0.55562 (13)	0.0200 (4)
C8B	0.5642 (2)	0.3868 (2)	0.61213 (14)	0.0193 (4)
C9B	0.51012 (19)	0.40097 (19)	0.69749 (13)	0.0175 (4)
C10B	0.42110 (19)	0.30043 (19)	0.72675 (13)	0.0173 (4)
C11B	0.30626 (19)	0.2160 (2)	0.86651 (12)	0.0161 (4)
C12B	0.1834 (2)	0.2501 (2)	0.90227 (13)	0.0185 (4)
C13B	0.1267 (2)	0.1686 (2)	0.96236 (14)	0.0223 (4)
C14B	0.1912 (2)	0.0542 (2)	0.98908 (14)	0.0228 (4)
C15B	0.3122 (2)	0.0188 (2)	0.95183 (14)	0.0218 (4)
C16B	0.36828 (19)	0.0984 (2)	0.89061 (13)	0.0192 (4)
C17B	0.2224 (2)	0.0005 (2)	0.62431 (15)	0.0236 (4)
C18B	0.6704 (2)	0.3438 (2)	0.44447 (16)	0.0266 (5)
O1B	0.28035 (15)	0.10469 (14)	0.68888 (9)	0.0238 (3)
O2B	0.57054 (16)	0.25043 (15)	0.47225 (9)	0.0276 (3)
H3A	−0.102 (3)	0.527 (3)	0.3972 (17)	0.030 (7)*
H6A	0.290 (2)	0.816 (2)	0.1237 (16)	0.020 (5)*
H8A	0.220 (2)	0.987 (3)	0.3705 (16)	0.026 (6)*
H16A	0.193 (2)	0.414 (2)	0.2432 (15)	0.021 (6)*
H14A	−0.053 (2)	0.098 (3)	0.1641 (16)	0.027 (6)*
H13A	−0.241 (3)	0.218 (3)	0.1921 (19)	0.038 (7)*
H15A	0.163 (3)	0.187 (3)	0.1838 (16)	0.033 (6)*
H3B	0.394 (2)	0.452 (2)	0.9274 (17)	0.027 (6)*
H8B	0.622 (2)	0.455 (2)	0.5995 (15)	0.021 (6)*
H12B	0.140 (2)	0.327 (2)	0.8887 (13)	0.010 (5)*
H13B	0.051 (3)	0.194 (3)	0.9858 (18)	0.038 (7)*
H16B	0.451 (2)	0.079 (2)	0.8690 (15)	0.020 (5)*
H15B	0.363 (2)	−0.057 (3)	0.9700 (16)	0.026 (6)*
H6B	0.406 (2)	0.113 (2)	0.5367 (17)	0.024 (6)*
H12A	−0.217 (3)	0.436 (2)	0.2490 (15)	0.029 (6)*
H181	0.480 (3)	1.150 (3)	0.2743 (19)	0.038 (7)*
H182	0.340 (3)	1.171 (3)	0.3149 (17)	0.033 (7)*
H183	0.444 (2)	1.058 (2)	0.3530 (17)	0.027 (6)*
H171	0.163 (2)	0.683 (2)	0.0128 (16)	0.022 (5)*
H172	0.152 (3)	0.531 (3)	0.012 (2)	0.042 (7)*
H173	0.283 (3)	0.593 (3)	0.0583 (17)	0.028 (6)*
H282	0.748 (3)	0.348 (3)	0.4829 (18)	0.032 (7)*
H281	0.634 (2)	0.429 (3)	0.4422 (15)	0.023 (6)*
H283	0.688 (3)	0.308 (3)	0.3863 (19)	0.032 (7)*
H273	0.156 (3)	−0.042 (3)	0.6514 (19)	0.043 (8)*
H272	0.298 (3)	−0.065 (3)	0.6064 (16)	0.034 (6)*
H271	0.177 (2)	0.035 (2)	0.5686 (17)	0.027 (6)*
H14B	0.151 (2)	0.000 (2)	1.0286 (16)	0.022 (6)*

	U11	U22	U33	U12	U13	U23
Br1A	0.03787 (17)	0.02967 (17)	0.01893 (16)	0.00803 (11)	0.01470 (11)	0.00473 (11)
N1A	0.0251 (9)	0.0211 (9)	0.0169 (8)	0.0059 (7)	0.0071 (7)	0.0031 (7)
C2A	0.0236 (10)	0.0240 (11)	0.0147 (9)	0.0077 (8)	0.0072 (8)	0.0052 (8)
C3A	0.0243 (10)	0.0216 (11)	0.0231 (11)	0.0050 (8)	0.0082 (8)	0.0065 (9)
C4A	0.0174 (9)	0.0207 (10)	0.0183 (10)	0.0042 (7)	0.0030 (7)	0.0039 (8)
C5A	0.0183 (9)	0.0176 (10)	0.0175 (9)	0.0043 (7)	0.0037 (7)	0.0011 (8)
C6A	0.0209 (9)	0.0200 (10)	0.0150 (10)	0.0042 (8)	0.0056 (8)	0.0034 (8)
C7A	0.0202 (9)	0.0173 (9)	0.0223 (10)	0.0031 (7)	0.0022 (8)	0.0047 (8)
C8A	0.0244 (10)	0.0185 (10)	0.0183 (10)	0.0025 (8)	0.0038 (8)	−0.0015 (8)
C9A	0.0211 (9)	0.0199 (10)	0.0157 (10)	0.0074 (8)	0.0035 (7)	0.0037 (8)
C10A	0.0184 (9)	0.0188 (10)	0.0171 (10)	0.0055 (7)	0.0021 (7)	0.0034 (8)
C11A	0.0224 (10)	0.0219 (11)	0.0137 (10)	0.0018 (8)	0.0039 (8)	0.0047 (8)
C12A	0.0190 (10)	0.0286 (11)	0.0192 (10)	0.0026 (9)	0.0026 (8)	0.0062 (9)
C13A	0.0233 (11)	0.0311 (12)	0.0242 (11)	−0.0072 (9)	−0.0001 (9)	0.0030 (9)
C14A	0.0390 (12)	0.0202 (12)	0.0192 (11)	−0.0047 (9)	0.0023 (9)	−0.0030 (9)
C15A	0.0283 (11)	0.0273 (11)	0.0156 (10)	0.0055 (9)	0.0042 (8)	−0.0002 (8)
C16A	0.0187 (10)	0.0246 (11)	0.0159 (10)	0.0008 (8)	0.0035 (8)	0.0028 (8)
C17A	0.0328 (13)	0.0314 (13)	0.0165 (10)	0.0019 (10)	0.0095 (9)	−0.0040 (9)
C18A	0.0297 (11)	0.0227 (11)	0.0252 (12)	−0.0050 (9)	−0.0003 (9)	0.0021 (9)
O1A	0.0274 (7)	0.0233 (7)	0.0146 (7)	−0.0021 (6)	0.0081 (5)	−0.0027 (6)
O2A	0.0268 (7)	0.0205 (7)	0.0226 (8)	−0.0052 (6)	0.0074 (6)	0.0002 (6)
Br1B	0.03604 (17)	0.01914 (16)	0.01965 (16)	−0.00615 (10)	−0.00020 (10)	−0.00227 (10)
N1B	0.0190 (8)	0.0197 (9)	0.0170 (8)	−0.0013 (6)	0.0007 (6)	0.0009 (7)
C2B	0.0220 (9)	0.0152 (9)	0.0165 (10)	0.0003 (7)	−0.0026 (8)	−0.0009 (7)
C3B	0.0219 (10)	0.0200 (10)	0.0157 (10)	0.0011 (8)	0.0026 (8)	0.0021 (8)
C4B	0.0147 (9)	0.0182 (10)	0.0176 (10)	0.0021 (7)	0.0004 (7)	0.0012 (8)
C5B	0.0190 (9)	0.0167 (10)	0.0191 (10)	0.0010 (7)	0.0000 (7)	0.0032 (8)
C6B	0.0237 (10)	0.0191 (10)	0.0183 (10)	0.0003 (8)	0.0031 (8)	−0.0027 (8)
C7B	0.0236 (10)	0.0236 (11)	0.0140 (10)	0.0046 (8)	0.0053 (8)	0.0031 (8)
C8B	0.0202 (10)	0.0204 (10)	0.0185 (10)	−0.0003 (8)	0.0048 (8)	0.0059 (8)
C9B	0.0169 (9)	0.0179 (10)	0.0176 (9)	0.0012 (7)	−0.0011 (7)	0.0028 (8)
C10B	0.0170 (9)	0.0196 (10)	0.0157 (9)	0.0028 (7)	0.0011 (7)	0.0033 (8)
C11B	0.0183 (9)	0.0190 (10)	0.0105 (9)	−0.0033 (7)	0.0009 (7)	−0.0017 (7)
C12B	0.0188 (9)	0.0184 (11)	0.0179 (10)	0.0019 (8)	0.0013 (8)	−0.0023 (8)
C13B	0.0180 (10)	0.0284 (11)	0.0208 (10)	−0.0014 (8)	0.0071 (8)	−0.0035 (8)
C14B	0.0274 (10)	0.0226 (11)	0.0182 (10)	−0.0087 (8)	0.0057 (8)	0.0003 (8)
C15B	0.0255 (10)	0.0180 (10)	0.0216 (10)	0.0010 (8)	0.0012 (8)	0.0007 (8)
C16B	0.0180 (10)	0.0205 (10)	0.0189 (10)	−0.0003 (8)	0.0046 (8)	−0.0032 (8)
C17B	0.0263 (11)	0.0195 (11)	0.0238 (11)	−0.0040 (9)	0.0018 (9)	−0.0044 (9)
C18B	0.0319 (12)	0.0260 (12)	0.0246 (12)	0.0037 (10)	0.0134 (10)	0.0073 (9)
O1B	0.0283 (7)	0.0234 (7)	0.0192 (7)	−0.0094 (6)	0.0055 (6)	−0.0020 (6)
O2B	0.0366 (8)	0.0284 (8)	0.0195 (8)	−0.0021 (6)	0.0152 (6)	−0.0023 (6)

Br1A—C2A	1.9168 (19)	Br1B—C2B	1.9147 (19)
N1A—C2A	1.296 (3)	N1B—C2B	1.302 (3)
N1A—C9A	1.374 (3)	N1B—C9B	1.370 (3)
C2A—C3A	1.392 (3)	C2B—C3B	1.393 (3)
C3A—C4A	1.388 (3)	C3B—C4B	1.376 (3)
C3A—H3A	0.92 (3)	C3B—H3B	0.97 (3)
C4A—C10A	1.422 (3)	C4B—C10B	1.427 (3)
C4A—C11A	1.487 (3)	C4B—C11B	1.497 (3)
C5A—O1A	1.364 (2)	C5B—O1B	1.350 (2)
C5A—C6A	1.370 (3)	C5B—C6B	1.369 (3)
C5A—C10A	1.440 (3)	C5B—C10B	1.440 (3)
C6A—C7A	1.412 (3)	C6B—C7B	1.419 (3)
C6A—H6A	0.98 (2)	C6B—H6B	0.89 (3)
C7A—C8A	1.363 (3)	C7B—O2B	1.362 (2)
C7A—O2A	1.364 (2)	C7B—C8B	1.363 (3)
C8A—C9A	1.413 (3)	C8B—C9B	1.414 (3)
C8A—H8A	0.93 (3)	C8B—H8B	0.91 (2)
C9A—C10A	1.426 (3)	C9B—C10B	1.420 (3)
C11A—C12A	1.395 (3)	C11B—C16B	1.389 (3)
C11A—C16A	1.402 (3)	C11B—C12B	1.399 (3)
C12A—C13A	1.387 (3)	C12B—C13B	1.382 (3)
C12A—H12A	0.95 (3)	C12B—H12B	0.92 (2)
C13A—C14A	1.379 (3)	C13B—C14B	1.383 (3)
C13A—H13A	0.89 (3)	C13B—H13B	0.89 (3)
C14A—C15A	1.389 (3)	C14B—C15B	1.395 (3)
C14A—H14A	0.87 (3)	C14B—H14B	0.92 (2)
C15A—C16A	1.379 (3)	C15B—C16B	1.380 (3)
C15A—H15A	0.97 (3)	C15B—H15B	0.96 (3)
C16A—H16A	0.93 (2)	C16B—H16B	0.92 (2)
C17A—O1A	1.426 (2)	C17B—O1B	1.435 (2)
C17A—H171	0.99 (2)	C17B—H273	0.90 (3)
C17A—H172	0.88 (3)	C17B—H272	1.05 (3)
C17A—H173	0.95 (3)	C17B—H271	0.99 (2)
C18A—O2A	1.435 (3)	C18B—O2B	1.432 (3)
C18A—H181	0.90 (3)	C18B—H282	0.91 (3)
C18A—H182	1.00 (3)	C18B—H281	0.94 (3)
C18A—H183	0.99 (3)	C18B—H283	0.95 (3)
C2A—N1A—C9A	116.40 (17)	C2B—N1B—C9B	116.28 (17)
N1A—C2A—C3A	126.61 (18)	N1B—C2B—C3B	126.12 (18)
N1A—C2A—Br1A	115.79 (15)	N1B—C2B—Br1B	116.34 (14)
C3A—C2A—Br1A	117.47 (15)	C3B—C2B—Br1B	117.52 (14)
C4A—C3A—C2A	118.63 (19)	C4B—C3B—C2B	118.86 (18)
C4A—C3A—H3A	118.2 (16)	C4B—C3B—H3B	120.4 (15)
C2A—C3A—H3A	123.0 (16)	C2B—C3B—H3B	120.7 (15)
C3A—C4A—C10A	117.62 (18)	C3B—C4B—C10B	117.97 (18)
C3A—C4A—C11A	115.29 (18)	C3B—C4B—C11B	115.31 (17)
C10A—C4A—C11A	126.82 (17)	C10B—C4B—C11B	126.54 (17)
O1A—C5A—C6A	123.19 (17)	O1B—C5B—C6B	123.94 (18)
O1A—C5A—C10A	115.72 (16)	O1B—C5B—C10B	115.64 (16)
C6A—C5A—C10A	121.07 (18)	C6B—C5B—C10B	120.40 (18)
C5A—C6A—C7A	120.33 (17)	C5B—C6B—C7B	120.30 (19)
C5A—C6A—H6A	122.2 (13)	C5B—C6B—H6B	125.0 (15)
C7A—C6A—H6A	117.5 (13)	C7B—C6B—H6B	114.7 (15)
C8A—C7A—O2A	124.71 (18)	O2B—C7B—C8B	124.74 (19)
C8A—C7A—C6A	121.31 (18)	O2B—C7B—C6B	113.86 (18)
O2A—C7A—C6A	113.98 (16)	C8B—C7B—C6B	121.38 (19)
C7A—C8A—C9A	118.89 (18)	C7B—C8B—C9B	118.94 (19)
C7A—C8A—H8A	122.6 (14)	C7B—C8B—H8B	125.6 (15)
C9A—C8A—H8A	118.5 (14)	C9B—C8B—H8B	115.4 (15)
N1A—C9A—C8A	115.57 (17)	N1B—C9B—C8B	115.72 (17)
N1A—C9A—C10A	122.43 (17)	N1B—C9B—C10B	122.91 (17)
C8A—C9A—C10A	121.98 (17)	C8B—C9B—C10B	121.37 (17)
C4A—C10A—C9A	118.10 (17)	C9B—C10B—C4B	117.57 (17)
C4A—C10A—C5A	125.79 (18)	C9B—C10B—C5B	117.28 (17)
C9A—C10A—C5A	116.11 (17)	C4B—C10B—C5B	125.13 (18)
C12A—C11A—C16A	118.49 (19)	C16B—C11B—C12B	119.27 (18)
C12A—C11A—C4A	120.08 (18)	C16B—C11B—C4B	120.99 (17)
C16A—C11A—C4A	120.93 (17)	C12B—C11B—C4B	118.87 (17)
C13A—C12A—C11A	120.8 (2)	C13B—C12B—C11B	119.92 (19)
C13A—C12A—H12A	118.8 (14)	C13B—C12B—H12B	118.0 (13)
C11A—C12A—H12A	120.3 (14)	C11B—C12B—H12B	122.0 (13)
C14A—C13A—C12A	120.2 (2)	C12B—C13B—C14B	120.80 (19)
C14A—C13A—H13A	120.2 (18)	C12B—C13B—H13B	118.1 (18)
C12A—C13A—H13A	119.6 (18)	C14B—C13B—H13B	121.0 (18)
C13A—C14A—C15A	119.7 (2)	C13B—C14B—C15B	119.15 (19)
C13A—C14A—H14A	121.3 (15)	C13B—C14B—H14B	119.4 (14)
C15A—C14A—H14A	119.1 (15)	C15B—C14B—H14B	121.4 (14)
C16A—C15A—C14A	120.6 (2)	C16B—C15B—C14B	120.41 (19)
C16A—C15A—H15A	122.8 (15)	C16B—C15B—H15B	117.0 (14)
C14A—C15A—H15A	116.6 (15)	C14B—C15B—H15B	122.5 (14)
C15A—C16A—C11A	120.26 (19)	C15B—C16B—C11B	120.38 (18)
C15A—C16A—H16A	121.2 (14)	C15B—C16B—H16B	120.7 (14)
C11A—C16A—H16A	118.4 (14)	C11B—C16B—H16B	118.7 (14)
O1A—C17A—H171	109.2 (13)	O1B—C17B—H273	106.0 (19)
O1A—C17A—H172	106.1 (18)	O1B—C17B—H272	110.5 (13)
H171—C17A—H172	108 (2)	H273—C17B—H272	111 (2)
O1A—C17A—H173	110.7 (15)	O1B—C17B—H271	113.2 (14)
H171—C17A—H173	114 (2)	H273—C17B—H271	107 (2)
H172—C17A—H173	109 (2)	H272—C17B—H271	108.9 (19)
O2A—C18A—H181	100.4 (18)	O2B—C18B—H282	111.3 (16)
O2A—C18A—H182	112.2 (15)	O2B—C18B—H281	110.0 (14)
H181—C18A—H182	111 (2)	H282—C18B—H281	109 (2)
O2A—C18A—H183	107.3 (14)	O2B—C18B—H283	103.4 (16)
H181—C18A—H183	114 (2)	H282—C18B—H283	110 (2)
H182—C18A—H183	111 (2)	H281—C18B—H283	112 (2)
C5A—O1A—C17A	118.03 (16)	C5B—O1B—C17B	118.11 (16)
C7A—O2A—C18A	116.35 (16)	C7B—O2B—C18B	116.83 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C16A—H16A···N1Bi	0.93 (2)	2.59 (2)	3.497 (3)	167 (2)
C16B—H16B···O2Ai	0.92 (2)	2.54 (2)	3.437 (2)	163 (2)
C17B—H272···O2Bii	1.04 (3)	2.57 (3)	3.580 (3)	164 (2)
C12A—H12A···Cg1iii	0.95 (3)	2.87 (3)	3.762 (2)	158 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16A—H16A⋯N1Bi	0.93 (2)	2.59 (2)	3.497 (3)	167 (2)
C16B—H16B⋯O2Ai	0.92 (2)	2.54 (2)	3.437 (2)	163 (2)
C17B—H272⋯O2Bii	1.04 (3)	2.57 (3)	3.580 (3)	164 (2)
C12A—H12A⋯Cg1iii	0.95 (3)	2.87 (3)	3.762 (2)	158 (2)

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the N1B/C2B–C4B/C9B/C10B ring.