4-Chloro-N-(3-methoxy-phen-yl)-benz-amide.

The title benzamide derivative, C(14)H(12)ClNO(2), crystallizes with two independent mol-ecules in the asymmetric unit. Both are close to being planar, with dihedral angles between the two benzene rings of 11.92 (6) and 12.80 (7)°. In the crystal structure, N-H⋯O hydrogen bonds link mol-ecules into chains along a. These inter-actions are augmented by C-H⋯O hydrogen bonds to form two-dimensional layers in the ac plane. Additional C-H⋯O inter-actions result in a three-dimensional network consisting of undulating rows along c. The crystal studied was an inversion twin with a 0.59 (3):0.41 (3) domain ratio.

Related literature

For background on the applications of benzanilides, see: Zhichkin et al. (2007 ▶); Igawa et al. (1999 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H12ClNO2

M = 261.70

Orthorhombic,

a = 9.6952 (4) Å

b = 10.5671 (3) Å

c = 24.3512 (8) Å

V = 2494.78 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.30 mm−1

T = 91 (2) K

0.80 × 0.27 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.771, T max = 0.948

47170 measured reflections

8997 independent reflections

8334 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.087

S = 1.05

8997 reflections

336 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 3581 Friedel pairs

Flack parameter: 0.59 (3)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: n class="Gene">APEX2 and SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029899/hb2792sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029899/hb2792Isup2.hkl

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

C14H12ClNO2	F(000) = 1088
Mr = 261.70	Dx = 1.393 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8842 reflections
a = 9.6952 (4) Å	θ = 2.3–32.7°
b = 10.5671 (3) Å	µ = 0.30 mm−1
c = 24.3512 (8) Å	T = 91 K
V = 2494.78 (15) Å3	Rod, colourless
Z = 8	0.80 × 0.27 × 0.18 mm

Bruker APEXII CCD area-detector diffractometer	8997 independent reflections
Radiation source: fine-focus sealed tube	8334 reflections with I > 2σ(I)
graphite	Rint = 0.038
ω scans	θmax = 33.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −14→11
Tmin = 0.771, Tmax = 0.948	k = −16→16
47170 measured reflections	l = −35→36

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0497P)2 + 0.3361P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
8997 reflections	Δρmax = 0.43 e Å−3
336 parameters	Δρmin = −0.26 e Å−3
0 restraints	Absolute structure: Flack (1983), 3581 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.59 (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	0.44661 (12)	−0.01256 (11)	0.37778 (4)	0.01480 (19)
O1A	0.33061 (9)	−0.01825 (10)	0.39873 (4)	0.0241 (2)
C2A	0.46264 (12)	0.02718 (10)	0.31915 (4)	0.01340 (18)
C3A	0.36632 (12)	0.11223 (11)	0.29781 (5)	0.0164 (2)
H3A	0.2946	0.1434	0.3207	0.020*
C4A	0.37391 (13)	0.15185 (11)	0.24357 (5)	0.0172 (2)
H4A	0.3095	0.2113	0.2295	0.021*
C5A	0.47765 (13)	0.10288 (10)	0.21016 (4)	0.0166 (2)
Cl1A	0.48931 (4)	0.15338 (3)	0.142463 (11)	0.02479 (7)
C6A	0.57279 (13)	0.01592 (11)	0.22997 (4)	0.0175 (2)
H6A	0.6418	−0.0180	0.2065	0.021*
C7A	0.56516 (12)	−0.02073 (10)	0.28487 (4)	0.01525 (19)
H7A	0.6306	−0.0791	0.2991	0.018*
N1A	0.56370 (10)	−0.04026 (9)	0.40506 (4)	0.01410 (17)
H1NA	0.6396 (18)	−0.0282 (16)	0.3886 (7)	0.021 (4)*
C8A	0.57503 (12)	−0.08292 (10)	0.46008 (4)	0.01315 (18)
C9A	0.47507 (12)	−0.05885 (10)	0.49949 (4)	0.01510 (19)
H9A	0.3933	−0.0145	0.4899	0.018*
C10A	0.49561 (12)	−0.10044 (10)	0.55337 (4)	0.0160 (2)
O2A	0.39068 (10)	−0.07027 (9)	0.58869 (3)	0.02047 (17)
C14A	0.39789 (14)	−0.11940 (12)	0.64324 (5)	0.0224 (2)
H14A	0.3922	−0.2120	0.6421	0.034*
H14B	0.3210	−0.0859	0.6650	0.034*
H14C	0.4854	−0.0941	0.6601	0.034*
C11A	0.61594 (13)	−0.16314 (11)	0.56841 (5)	0.0179 (2)
H11A	0.6298	−0.1903	0.6052	0.021*
C12A	0.71576 (13)	−0.18529 (11)	0.52836 (5)	0.0185 (2)
H12A	0.7989	−0.2270	0.5383	0.022*
C13A	0.69619 (12)	−0.14772 (11)	0.47434 (5)	0.0162 (2)
H13A	0.7641	−0.1656	0.4473	0.019*
C1B	−0.05241 (12)	−0.00261 (10)	0.37999 (4)	0.01368 (19)
O1B	−0.16985 (9)	−0.00419 (9)	0.36016 (3)	0.01997 (17)
C2B	−0.02802 (12)	0.04716 (10)	0.43684 (4)	0.01360 (18)
C3B	0.07492 (12)	−0.00094 (11)	0.47086 (4)	0.01501 (19)
H3B	0.1339	−0.0660	0.4577	0.018*
C4B	0.09238 (13)	0.04536 (11)	0.52393 (4)	0.0172 (2)
H4B	0.1618	0.0118	0.5473	0.021*
C5B	0.00613 (13)	0.14154 (10)	0.54198 (4)	0.0171 (2)
Cl1B	0.02837 (4)	0.19996 (3)	0.608166 (12)	0.02653 (7)
C6B	−0.09805 (13)	0.19097 (11)	0.50899 (5)	0.0193 (2)
H6B	−0.1558	0.2570	0.5221	0.023*
C7B	−0.11618 (13)	0.14216 (11)	0.45660 (5)	0.0174 (2)
H7B	−0.1886	0.1732	0.4340	0.021*
N1B	0.06041 (10)	−0.04339 (9)	0.35250 (4)	0.01450 (17)
H1NB	0.1425 (18)	−0.0346 (16)	0.3682 (7)	0.021 (4)*
C8B	0.06282 (12)	−0.09968 (10)	0.29958 (4)	0.01377 (19)
C9B	−0.04236 (12)	−0.08284 (11)	0.26127 (4)	0.0157 (2)
H9B	−0.1206	−0.0327	0.2701	0.019*
C10B	−0.03149 (13)	−0.14050 (11)	0.20975 (4)	0.0163 (2)
O2B	−0.14035 (10)	−0.11702 (9)	0.17528 (4)	0.02185 (18)
C14B	−0.13097 (13)	−0.16277 (12)	0.12016 (4)	0.0205 (2)
H14D	−0.0436	−0.1350	0.1039	0.031*
H14E	−0.2080	−0.1292	0.0985	0.031*
H14F	−0.1349	−0.2554	0.1202	0.031*
C11B	0.08319 (13)	−0.21239 (11)	0.19574 (5)	0.0193 (2)
H11B	0.0899	−0.2509	0.1606	0.023*
C12B	0.18814 (14)	−0.22688 (12)	0.23434 (5)	0.0204 (2)
H12B	0.2675	−0.2751	0.2251	0.024*
C13B	0.17912 (13)	−0.17224 (11)	0.28614 (5)	0.0175 (2)
H13B	0.2510	−0.1839	0.3122	0.021*

	U11	U22	U33	U12	U13	U23
C1A	0.0113 (5)	0.0201 (5)	0.0130 (4)	−0.0011 (4)	−0.0008 (4)	0.0000 (3)
O1A	0.0102 (4)	0.0468 (6)	0.0152 (4)	−0.0008 (4)	0.0008 (3)	0.0043 (4)
C2A	0.0114 (5)	0.0159 (4)	0.0129 (4)	−0.0015 (4)	−0.0004 (4)	−0.0008 (3)
C3A	0.0152 (5)	0.0199 (5)	0.0142 (4)	0.0028 (4)	−0.0003 (4)	−0.0018 (4)
C4A	0.0194 (5)	0.0167 (4)	0.0155 (4)	0.0020 (4)	−0.0035 (4)	−0.0001 (4)
C5A	0.0193 (5)	0.0188 (4)	0.0116 (4)	−0.0043 (4)	−0.0018 (4)	0.0007 (3)
Cl1A	0.03200 (17)	0.02910 (14)	0.01326 (10)	−0.00233 (12)	0.00006 (11)	0.00451 (9)
C6A	0.0160 (5)	0.0236 (5)	0.0129 (4)	0.0002 (4)	0.0015 (4)	−0.0023 (4)
C7A	0.0126 (5)	0.0188 (4)	0.0143 (4)	0.0016 (4)	−0.0010 (4)	−0.0014 (4)
N1A	0.0097 (4)	0.0202 (4)	0.0124 (4)	−0.0002 (3)	0.0005 (3)	0.0010 (3)
C8A	0.0125 (5)	0.0151 (4)	0.0118 (4)	−0.0022 (4)	−0.0016 (4)	0.0005 (3)
C9A	0.0130 (5)	0.0179 (4)	0.0144 (4)	0.0006 (4)	−0.0009 (4)	0.0008 (3)
C10A	0.0164 (5)	0.0173 (4)	0.0143 (4)	−0.0004 (4)	0.0004 (4)	0.0005 (3)
O2A	0.0190 (4)	0.0299 (4)	0.0125 (3)	0.0046 (4)	0.0033 (3)	0.0028 (3)
C14A	0.0258 (6)	0.0283 (6)	0.0129 (4)	−0.0009 (5)	0.0033 (5)	0.0034 (4)
C11A	0.0192 (5)	0.0199 (5)	0.0145 (4)	0.0013 (4)	−0.0012 (4)	0.0036 (4)
C12A	0.0170 (5)	0.0191 (5)	0.0194 (5)	0.0036 (4)	−0.0018 (4)	0.0036 (4)
C13A	0.0132 (5)	0.0182 (5)	0.0174 (5)	0.0012 (4)	0.0012 (4)	0.0019 (4)
C1B	0.0103 (5)	0.0179 (4)	0.0128 (4)	0.0003 (4)	0.0025 (3)	0.0020 (3)
O1B	0.0096 (4)	0.0351 (5)	0.0152 (3)	0.0004 (3)	0.0008 (3)	−0.0002 (3)
C2B	0.0115 (5)	0.0172 (4)	0.0121 (4)	−0.0004 (4)	0.0022 (4)	0.0015 (3)
C3B	0.0129 (5)	0.0187 (4)	0.0135 (4)	0.0023 (4)	0.0020 (4)	−0.0005 (4)
C4B	0.0157 (5)	0.0220 (5)	0.0138 (4)	0.0014 (4)	0.0010 (4)	−0.0009 (4)
C5B	0.0197 (6)	0.0184 (4)	0.0133 (4)	−0.0021 (4)	0.0040 (4)	−0.0032 (3)
Cl1B	0.03451 (17)	0.02830 (14)	0.01679 (11)	−0.00085 (13)	0.00243 (12)	−0.00894 (10)
C6B	0.0214 (6)	0.0177 (4)	0.0188 (5)	0.0048 (4)	0.0065 (4)	−0.0002 (4)
C7B	0.0160 (5)	0.0206 (5)	0.0157 (5)	0.0037 (4)	0.0030 (4)	0.0026 (4)
N1B	0.0094 (4)	0.0220 (4)	0.0121 (4)	0.0009 (3)	−0.0001 (3)	−0.0009 (3)
C8B	0.0129 (5)	0.0172 (4)	0.0113 (4)	−0.0006 (4)	0.0017 (4)	0.0005 (3)
C9B	0.0134 (5)	0.0201 (5)	0.0137 (4)	0.0022 (4)	0.0008 (4)	−0.0011 (4)
C10B	0.0158 (5)	0.0199 (5)	0.0133 (4)	0.0009 (4)	−0.0003 (4)	−0.0008 (3)
O2B	0.0181 (4)	0.0333 (5)	0.0142 (3)	0.0051 (4)	−0.0031 (3)	−0.0068 (3)
C14B	0.0219 (6)	0.0268 (5)	0.0127 (4)	−0.0008 (5)	0.0004 (4)	−0.0045 (4)
C11B	0.0203 (6)	0.0210 (5)	0.0165 (5)	0.0044 (4)	0.0011 (4)	−0.0033 (4)
C12B	0.0182 (6)	0.0234 (5)	0.0195 (5)	0.0075 (5)	0.0008 (4)	−0.0022 (4)
C13B	0.0147 (5)	0.0215 (5)	0.0164 (5)	0.0044 (4)	0.0003 (4)	−0.0004 (4)

C1A—O1A	1.2364 (14)	C1B—O1B	1.2369 (14)
C1A—N1A	1.3475 (14)	C1B—N1B	1.3529 (14)
C1A—C2A	1.4964 (14)	C1B—C2B	1.4997 (14)
C2A—C7A	1.3932 (15)	C2B—C3B	1.3931 (15)
C2A—C3A	1.3963 (15)	C2B—C7B	1.4035 (15)
C3A—C4A	1.3875 (15)	C3B—C4B	1.3920 (15)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.3933 (17)	C4B—C5B	1.3876 (16)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—C6A	1.3884 (17)	C5B—C6B	1.3921 (17)
C5A—Cl1A	1.7364 (10)	C5B—Cl1B	1.7394 (11)
C6A—C7A	1.3939 (15)	C6B—C7B	1.3872 (16)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—H7A	0.9500	C7B—H7B	0.9500
N1A—C8A	1.4178 (13)	N1B—C8B	1.4194 (13)
N1A—H1NA	0.847 (18)	N1B—H1NB	0.887 (18)
C8A—C9A	1.3874 (15)	C8B—C9B	1.3936 (16)
C8A—C13A	1.4033 (16)	C8B—C13B	1.4023 (16)
C9A—C10A	1.3980 (14)	C9B—C10B	1.3987 (14)
C9A—H9A	0.9500	C9B—H9B	0.9500
C10A—O2A	1.3697 (14)	C10B—O2B	1.3711 (14)
C10A—C11A	1.3908 (17)	C10B—C11B	1.3891 (17)
O2A—C14A	1.4281 (14)	O2B—C14B	1.4295 (13)
C14A—H14A	0.9800	C14B—H14D	0.9800
C14A—H14B	0.9800	C14B—H14E	0.9800
C14A—H14C	0.9800	C14B—H14F	0.9800
C11A—C12A	1.3938 (17)	C11B—C12B	1.3936 (17)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.3869 (16)	C12B—C13B	1.3900 (16)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—H13A	0.9500	C13B—H13B	0.9500
O1A—C1A—N1A	123.52 (10)	O1B—C1B—N1B	123.15 (10)
O1A—C1A—C2A	120.13 (10)	O1B—C1B—C2B	120.68 (10)
N1A—C1A—C2A	116.35 (10)	N1B—C1B—C2B	116.17 (10)
C7A—C2A—C3A	119.22 (10)	C3B—C2B—C7B	119.56 (10)
C7A—C2A—C1A	122.94 (10)	C3B—C2B—C1B	122.27 (10)
C3A—C2A—C1A	117.79 (10)	C7B—C2B—C1B	118.12 (10)
C4A—C3A—C2A	120.86 (10)	C4B—C3B—C2B	120.73 (10)
C4A—C3A—H3A	119.6	C4B—C3B—H3B	119.6
C2A—C3A—H3A	119.6	C2B—C3B—H3B	119.6
C3A—C4A—C5A	118.82 (11)	C5B—C4B—C3B	118.56 (11)
C3A—C4A—H4A	120.6	C5B—C4B—H4B	120.7
C5A—C4A—H4A	120.6	C3B—C4B—H4B	120.7
C6A—C5A—C4A	121.50 (10)	C4B—C5B—C6B	121.96 (10)
C6A—C5A—Cl1A	119.34 (9)	C4B—C5B—Cl1B	118.60 (9)
C4A—C5A—Cl1A	119.16 (9)	C6B—C5B—Cl1B	119.43 (9)
C5A—C6A—C7A	118.81 (10)	C7B—C6B—C5B	118.88 (10)
C5A—C6A—H6A	120.6	C7B—C6B—H6B	120.6
C7A—C6A—H6A	120.6	C5B—C6B—H6B	120.6
C2A—C7A—C6A	120.76 (10)	C6B—C7B—C2B	120.27 (11)
C2A—C7A—H7A	119.6	C6B—C7B—H7B	119.9
C6A—C7A—H7A	119.6	C2B—C7B—H7B	119.9
C1A—N1A—C8A	126.89 (10)	C1B—N1B—C8B	126.59 (10)
C1A—N1A—H1NA	117.8 (11)	C1B—N1B—H1NB	118.6 (11)
C8A—N1A—H1NA	115.3 (11)	C8B—N1B—H1NB	114.8 (11)
C9A—C8A—C13A	120.19 (10)	C9B—C8B—C13B	120.13 (10)
C9A—C8A—N1A	122.76 (10)	C9B—C8B—N1B	122.83 (10)
C13A—C8A—N1A	117.00 (10)	C13B—C8B—N1B	117.02 (10)
C8A—C9A—C10A	119.48 (10)	C8B—C9B—C10B	119.33 (10)
C8A—C9A—H9A	120.3	C8B—C9B—H9B	120.3
C10A—C9A—H9A	120.3	C10B—C9B—H9B	120.3
O2A—C10A—C11A	124.65 (10)	O2B—C10B—C11B	124.39 (10)
O2A—C10A—C9A	114.22 (10)	O2B—C10B—C9B	114.35 (10)
C11A—C10A—C9A	121.10 (10)	C11B—C10B—C9B	121.25 (11)
C10A—O2A—C14A	117.59 (9)	C10B—O2B—C14B	117.69 (9)
O2A—C14A—H14A	109.5	O2B—C14B—H14D	109.5
O2A—C14A—H14B	109.5	O2B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
O2A—C14A—H14C	109.5	O2B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C10A—C11A—C12A	118.56 (10)	C10B—C11B—C12B	118.61 (10)
C10A—C11A—H11A	120.7	C10B—C11B—H11B	120.7
C12A—C11A—H11A	120.7	C12B—C11B—H11B	120.7
C13A—C12A—C11A	121.37 (11)	C13B—C12B—C11B	121.37 (11)
C13A—C12A—H12A	119.3	C13B—C12B—H12B	119.3
C11A—C12A—H12A	119.3	C11B—C12B—H12B	119.3
C12A—C13A—C8A	119.27 (10)	C12B—C13B—C8B	119.31 (11)
C12A—C13A—H13A	120.4	C12B—C13B—H13B	120.3
C8A—C13A—H13A	120.4	C8B—C13B—H13B	120.3
O1A—C1A—C2A—C7A	−146.54 (12)	O1B—C1B—C2B—C3B	147.65 (12)
N1A—C1A—C2A—C7A	33.66 (15)	N1B—C1B—C2B—C3B	−32.96 (15)
O1A—C1A—C2A—C3A	30.77 (16)	O1B—C1B—C2B—C7B	−29.90 (15)
N1A—C1A—C2A—C3A	−149.03 (11)	N1B—C1B—C2B—C7B	149.49 (10)
C7A—C2A—C3A—C4A	−1.76 (17)	C7B—C2B—C3B—C4B	−0.84 (17)
C1A—C2A—C3A—C4A	−179.17 (10)	C1B—C2B—C3B—C4B	−178.36 (10)
C2A—C3A—C4A—C5A	1.56 (17)	C2B—C3B—C4B—C5B	−0.79 (17)
C3A—C4A—C5A—C6A	−0.02 (17)	C3B—C4B—C5B—C6B	1.13 (17)
C3A—C4A—C5A—Cl1A	−179.20 (9)	C3B—C4B—C5B—Cl1B	−179.70 (9)
C4A—C5A—C6A—C7A	−1.29 (17)	C4B—C5B—C6B—C7B	0.20 (18)
Cl1A—C5A—C6A—C7A	177.90 (9)	Cl1B—C5B—C6B—C7B	−178.97 (9)
C3A—C2A—C7A—C6A	0.41 (16)	C5B—C6B—C7B—C2B	−1.86 (17)
C1A—C2A—C7A—C6A	177.69 (10)	C3B—C2B—C7B—C6B	2.19 (16)
C5A—C6A—C7A—C2A	1.08 (17)	C1B—C2B—C7B—C6B	179.81 (10)
O1A—C1A—N1A—C8A	1.95 (19)	O1B—C1B—N1B—C8B	−3.85 (18)
C2A—C1A—N1A—C8A	−178.25 (10)	C2B—C1B—N1B—C8B	176.77 (10)
C1A—N1A—C8A—C9A	−24.49 (17)	C1B—N1B—C8B—C9B	22.32 (17)
C1A—N1A—C8A—C13A	157.99 (11)	C1B—N1B—C8B—C13B	−159.27 (11)
C13A—C8A—C9A—C10A	−0.46 (16)	C13B—C8B—C9B—C10B	0.94 (17)
N1A—C8A—C9A—C10A	−177.90 (10)	N1B—C8B—C9B—C10B	179.31 (10)
C8A—C9A—C10A—O2A	179.44 (10)	C8B—C9B—C10B—O2B	−179.68 (10)
C8A—C9A—C10A—C11A	1.42 (17)	C8B—C9B—C10B—C11B	−1.12 (17)
C11A—C10A—O2A—C14A	−7.68 (17)	C11B—C10B—O2B—C14B	−4.22 (17)
C9A—C10A—O2A—C14A	174.37 (10)	C9B—C10B—O2B—C14B	174.29 (10)
O2A—C10A—C11A—C12A	−178.57 (11)	O2B—C10B—C11B—C12B	178.73 (12)
C9A—C10A—C11A—C12A	−0.76 (17)	C9B—C10B—C11B—C12B	0.32 (18)
C10A—C11A—C12A—C13A	−0.87 (18)	C10B—C11B—C12B—C13B	0.67 (19)
C11A—C12A—C13A—C8A	1.81 (18)	C11B—C12B—C13B—C8B	−0.83 (18)
C9A—C8A—C13A—C12A	−1.13 (17)	C9B—C8B—C13B—C12B	0.01 (17)
N1A—C8A—C13A—C12A	176.46 (10)	N1B—C8B—C13B—C12B	−178.44 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1NB···O1A	0.887 (18)	1.977 (18)	2.8638 (13)	176.4 (15)
C3B—H3B···O1A	0.95	2.44	3.0436 (14)	121
C4B—H4B···O2A	0.95	2.59	3.5134 (15)	165
N1A—H1NA···O1Bi	0.847 (18)	1.989 (18)	2.8309 (13)	172.0 (16)
C6A—H6A···O2Bi	0.95	2.48	3.3885 (15)	161
C7A—H7A···O1Bi	0.95	2.57	3.1611 (14)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1B—H1NB⋯O1A	0.887 (18)	1.977 (18)	2.8638 (13)	176.4 (15)
C3B—H3B⋯O1A	0.95	2.44	3.0436 (14)	121
C4B—H4B⋯O2A	0.95	2.59	3.5134 (15)	165
N1A—H1NA⋯O1Bi	0.847 (18)	1.989 (18)	2.8309 (13)	172.0 (16)
C6A—H6A⋯O2Bi	0.95	2.48	3.3885 (15)	161
C7A—H7A⋯O1Bi	0.95	2.57	3.1611 (14)	121

Symmetry code: (i) .