N'-[(E)-4-Bromo-benzyl-idene]-2-(4-isobutyl-phen-yl)propanohydrazide.

The asymmetric unit of the title compound, C(20)H(23)BrN(2)O, contains two independent mol-ecules (A and B), in which the orientations of the 4-isobutyl-phenyl units are different. The dihedral angle between the two benzene rings is 88.45 (8)° in mol-ecule A and 89.87 (8)° in mol-ecule B. Mol-ecules A and B are linked by a C-H⋯N hydrogen bond. In the crystal, mol-ecules are linked into chains running along the a axis by inter-molcular N-H⋯O and C-H⋯O hydrogen bonds. The crystal structure is further stabilized by C-H⋯π inter-actions. The presence of pseudosymmetry in the structure suggests the higher symmetry space group Pbca. However, attempts to refine the structure in this space group resulted in a disorder model with high R (0.097) and wR (0.257) values. The crystal studied was an inversion twin with a 0.595 (4):0.405 (4) domain ratio.

Related literature

For the biological activities of hydrazone derivatives, see: Bedia et al. (2006 ▶); Rollas et al. (2002 ▶); Terzioglu & Gürsoy (2003 ▶); Sridhar & Perumal (2003 ▶); Amir & Kumar (2007 ▶). For a related structure, see: Fun et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H23BrN2O

M = 387.31

Orthorhombic,

a = 9.1440 (1) Å

b = 12.0110 (1) Å

c = 33.5670 (4) Å

V = 3686.62 (7) Å3

Z = 8

Mo Kα radiation

μ = 2.24 mm−1

T = 100 K

0.49 × 0.38 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.407, T max = 0.682

120355 measured reflections

20557 independent reflections

13317 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.103

S = 1.04

20557 reflections

448 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.72 e Å−3

Δρmin = −0.62 e Å−3

Absolute structure: Flack (1983 ▶), 9205 Friedel pairs

Flack parameter: 0.595 (4)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015542/ci2787sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015542/ci2787Isup2.hkl

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

C20H23BrN2O	F(000) = 1600
Mr = 387.31	Dx = 1.396 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9400 reflections
a = 9.1440 (1) Å	θ = 2.5–31.7°
b = 12.0110 (1) Å	µ = 2.24 mm−1
c = 33.5670 (4) Å	T = 100 K
V = 3686.62 (7) Å3	Block, colourless
Z = 8	0.49 × 0.38 × 0.19 mm

Bruker SMART APEXII CCD area-detector diffractometer	20557 independent reflections
Radiation source: fine-focus sealed tube	13317 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 38.6°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→16
Tmin = 0.407, Tmax = 0.682	k = −21→20
120355 measured reflections	l = −58→56

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0498P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
20557 reflections	Δρmax = 0.72 e Å−3
448 parameters	Δρmin = −0.61 e Å−3
0 restraints	Absolute structure: Flack (1983), 9205 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.595 (4)

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.849271 (19)	0.479672 (14)	0.078235 (6)	0.02563 (4)
O1A	0.88325 (12)	1.00346 (11)	0.27706 (3)	0.0213 (2)
N1A	0.73139 (15)	0.87330 (12)	0.22421 (4)	0.0173 (3)
N2A	0.66653 (15)	0.94990 (12)	0.24939 (4)	0.0164 (3)
C1A	0.81210 (19)	0.67440 (14)	0.17959 (5)	0.0184 (3)
H1AA	0.8601	0.6813	0.2039	0.022*
C2A	0.85669 (18)	0.59430 (13)	0.15259 (5)	0.0187 (3)
H2AA	0.9328	0.5460	0.1589	0.022*
C3A	0.78674 (19)	0.58675 (14)	0.11603 (5)	0.0189 (3)
C4A	0.6703 (2)	0.65496 (14)	0.10623 (5)	0.0211 (3)
H4AA	0.6243	0.6487	0.0816	0.025*
C5A	0.62366 (19)	0.73315 (14)	0.13401 (5)	0.0192 (3)
H5AA	0.5437	0.7781	0.1281	0.023*
C6A	0.6946 (2)	0.74535 (13)	0.17050 (5)	0.0165 (3)
C7A	0.64467 (19)	0.83222 (13)	0.19787 (5)	0.0176 (3)
H7AA	0.5490	0.8581	0.1962	0.021*
C8A	0.74894 (16)	1.00775 (15)	0.27548 (5)	0.0170 (3)
C9A	0.65950 (18)	1.07453 (13)	0.30584 (5)	0.0172 (3)
H9AA	0.5624	1.0888	0.2946	0.021*
C10A	0.64245 (16)	0.99942 (13)	0.34220 (4)	0.0155 (3)
C11A	0.51587 (18)	0.93583 (14)	0.34705 (5)	0.0185 (3)
H11A	0.4397	0.9428	0.3289	0.022*
C12A	0.50265 (19)	0.86228 (13)	0.37874 (5)	0.0182 (3)
H12A	0.4167	0.8217	0.3817	0.022*
C13A	0.61539 (18)	0.84797 (13)	0.40622 (4)	0.0172 (3)
C14A	0.74046 (17)	0.91272 (14)	0.40148 (5)	0.0204 (3)
H14A	0.8167	0.9056	0.4196	0.025*
C15A	0.75390 (17)	0.98781 (15)	0.37016 (5)	0.0200 (3)
H15A	0.8382	1.0307	0.3679	0.024*
C16A	0.60190 (19)	0.76581 (13)	0.43996 (5)	0.0194 (3)
H16A	0.6991	0.7508	0.4502	0.023*
H16B	0.5640	0.6965	0.4293	0.023*
C17A	0.50438 (19)	0.80147 (14)	0.47485 (5)	0.0219 (3)
H17A	0.4035	0.8064	0.4652	0.026*
C18A	0.5468 (3)	0.91335 (16)	0.49144 (6)	0.0442 (6)
H18A	0.5341	0.9693	0.4713	0.066*
H18B	0.6473	0.9116	0.4997	0.066*
H18C	0.4859	0.9305	0.5139	0.066*
C19A	0.5104 (2)	0.71186 (15)	0.50728 (5)	0.0274 (4)
H19A	0.4477	0.7328	0.5290	0.041*
H19B	0.6090	0.7046	0.5168	0.041*
H19C	0.4784	0.6420	0.4964	0.041*
C20A	0.73368 (19)	1.18646 (15)	0.31432 (6)	0.0229 (4)
H20A	0.6876	1.2212	0.3368	0.034*
H20B	0.7246	1.2339	0.2914	0.034*
H20C	0.8353	1.1744	0.3200	0.034*
Br1B	0.63994 (2)	−0.015149 (14)	0.077318 (5)	0.02449 (4)
O1B	0.61864 (12)	0.49983 (11)	0.27805 (3)	0.0206 (2)
N1B	0.77028 (15)	0.36554 (11)	0.22662 (4)	0.0161 (3)
N2B	0.83490 (16)	0.44565 (12)	0.25061 (4)	0.0165 (3)
C1B	0.68109 (19)	0.17270 (13)	0.18046 (5)	0.0175 (3)
H1BA	0.6314	0.1809	0.2045	0.021*
C2B	0.63144 (18)	0.09615 (13)	0.15256 (5)	0.0183 (3)
H2BA	0.5492	0.0529	0.1577	0.022*
C3B	0.7075 (2)	0.08541 (13)	0.11670 (5)	0.0190 (3)
C4B	0.83235 (19)	0.14694 (13)	0.10867 (5)	0.0190 (3)
H4BA	0.8824	0.1379	0.0848	0.023*
C5B	0.88101 (19)	0.22226 (13)	0.13705 (5)	0.0180 (3)
H5BA	0.9654	0.2633	0.1323	0.022*
C6B	0.8045 (2)	0.23731 (13)	0.17286 (5)	0.0164 (3)
C7B	0.85619 (19)	0.32373 (13)	0.20041 (5)	0.0175 (3)
H7BA	0.9524	0.3484	0.1988	0.021*
C8B	0.75320 (16)	0.50621 (14)	0.27594 (4)	0.0153 (3)
C9B	0.84083 (18)	0.58372 (12)	0.30309 (4)	0.0144 (3)
H9BA	0.9371	0.5957	0.2910	0.017*
C10B	0.86268 (16)	0.52286 (12)	0.34255 (4)	0.0146 (3)
C11B	0.96862 (18)	0.43906 (13)	0.34546 (5)	0.0165 (3)
H11B	1.0261	0.4219	0.3234	0.020*
C12B	0.98872 (19)	0.38154 (13)	0.38080 (5)	0.0188 (3)
H12B	1.0601	0.3265	0.3821	0.023*
C13B	0.90454 (18)	0.40422 (13)	0.41439 (5)	0.0182 (3)
C14B	0.80027 (18)	0.48834 (14)	0.41132 (5)	0.0205 (3)
H14B	0.7433	0.5056	0.4334	0.025*
C15B	0.77918 (18)	0.54699 (13)	0.37620 (5)	0.0182 (3)
H15B	0.7088	0.6028	0.3751	0.022*
C16B	0.9216 (2)	0.33528 (14)	0.45152 (5)	0.0215 (3)
H16C	0.8740	0.3733	0.4735	0.026*
H16D	1.0248	0.3293	0.4579	0.026*
C17B	0.85697 (19)	0.21766 (13)	0.44763 (5)	0.0195 (3)
H17B	0.9058	0.1806	0.4253	0.023*
C18B	0.8867 (2)	0.14987 (15)	0.48509 (5)	0.0313 (4)
H18D	0.8488	0.0759	0.4817	0.047*
H18E	0.8399	0.1847	0.5075	0.047*
H18F	0.9902	0.1463	0.4897	0.047*
C19B	0.6939 (2)	0.22087 (16)	0.43873 (6)	0.0285 (4)
H19D	0.6584	0.1464	0.4350	0.043*
H19E	0.6771	0.2634	0.4149	0.043*
H19F	0.6432	0.2549	0.4606	0.043*
C20B	0.76379 (18)	0.69647 (14)	0.30640 (5)	0.0190 (3)
H20D	0.8130	0.7416	0.3258	0.029*
H20E	0.6641	0.6853	0.3144	0.029*
H20F	0.7659	0.7332	0.2810	0.029*
H1NA	0.568 (2)	0.9602 (19)	0.2475 (6)	0.034 (6)*
H1NB	0.918 (2)	0.4564 (18)	0.2501 (6)	0.022 (6)*

	U11	U22	U33	U12	U13	U23
Br1A	0.02409 (8)	0.02207 (8)	0.03074 (9)	0.00076 (7)	0.00373 (8)	−0.00849 (8)
O1A	0.0144 (5)	0.0287 (6)	0.0207 (5)	0.0038 (5)	0.0014 (5)	−0.0010 (5)
N1A	0.0173 (7)	0.0183 (6)	0.0162 (7)	0.0044 (6)	0.0033 (5)	0.0026 (5)
N2A	0.0131 (6)	0.0205 (6)	0.0155 (6)	0.0042 (6)	0.0016 (5)	−0.0004 (5)
C1A	0.0171 (8)	0.0192 (7)	0.0188 (8)	0.0012 (7)	−0.0003 (7)	0.0027 (6)
C2A	0.0161 (8)	0.0172 (7)	0.0228 (8)	0.0033 (7)	0.0031 (7)	0.0018 (6)
C3A	0.0178 (8)	0.0179 (7)	0.0209 (8)	−0.0027 (7)	0.0042 (7)	−0.0021 (6)
C4A	0.0196 (8)	0.0222 (8)	0.0216 (8)	0.0005 (7)	−0.0010 (7)	−0.0018 (6)
C5A	0.0159 (8)	0.0193 (7)	0.0225 (8)	0.0028 (7)	−0.0008 (7)	0.0008 (6)
C6A	0.0152 (9)	0.0174 (7)	0.0169 (8)	0.0003 (6)	0.0018 (6)	0.0015 (6)
C7A	0.0162 (8)	0.0176 (7)	0.0190 (7)	0.0044 (7)	0.0014 (7)	0.0004 (6)
C8A	0.0170 (7)	0.0194 (8)	0.0146 (7)	0.0024 (7)	0.0025 (6)	0.0047 (6)
C9A	0.0137 (7)	0.0185 (7)	0.0194 (7)	0.0033 (7)	0.0019 (6)	0.0010 (6)
C10A	0.0143 (7)	0.0179 (6)	0.0144 (6)	0.0015 (6)	0.0024 (5)	−0.0011 (5)
C11A	0.0153 (7)	0.0213 (8)	0.0188 (8)	−0.0011 (6)	−0.0001 (6)	−0.0003 (6)
C12A	0.0180 (8)	0.0182 (7)	0.0185 (8)	−0.0042 (6)	0.0003 (6)	−0.0019 (6)
C13A	0.0183 (7)	0.0173 (6)	0.0160 (7)	−0.0005 (6)	0.0027 (6)	−0.0021 (5)
C14A	0.0160 (7)	0.0293 (8)	0.0160 (7)	−0.0025 (7)	−0.0004 (6)	0.0036 (6)
C15A	0.0133 (7)	0.0284 (8)	0.0184 (7)	−0.0060 (7)	−0.0002 (5)	0.0019 (6)
C16A	0.0206 (8)	0.0173 (7)	0.0203 (7)	0.0020 (6)	0.0031 (6)	0.0025 (6)
C17A	0.0228 (8)	0.0232 (8)	0.0197 (8)	0.0028 (7)	0.0051 (6)	0.0041 (6)
C18A	0.0875 (18)	0.0250 (9)	0.0202 (9)	0.0014 (11)	0.0156 (11)	−0.0014 (7)
C19A	0.0312 (10)	0.0280 (9)	0.0231 (8)	−0.0014 (8)	0.0046 (7)	0.0094 (7)
C20A	0.0222 (9)	0.0197 (8)	0.0269 (9)	0.0020 (7)	0.0041 (7)	0.0033 (7)
Br1B	0.03377 (10)	0.01815 (7)	0.02155 (8)	0.00059 (7)	−0.00595 (8)	−0.00540 (7)
O1B	0.0119 (5)	0.0290 (6)	0.0210 (5)	−0.0029 (5)	0.0010 (4)	−0.0038 (5)
N1B	0.0165 (6)	0.0165 (6)	0.0153 (6)	−0.0018 (6)	−0.0010 (5)	−0.0015 (5)
N2B	0.0129 (7)	0.0206 (7)	0.0160 (6)	−0.0039 (6)	0.0007 (5)	−0.0023 (5)
C1B	0.0196 (9)	0.0174 (7)	0.0154 (7)	0.0001 (7)	0.0008 (7)	0.0005 (6)
C2B	0.0186 (8)	0.0163 (6)	0.0200 (7)	0.0002 (7)	−0.0004 (7)	0.0016 (6)
C3B	0.0249 (8)	0.0126 (6)	0.0194 (8)	0.0011 (7)	−0.0037 (7)	−0.0018 (6)
C4B	0.0222 (8)	0.0185 (7)	0.0161 (7)	0.0041 (7)	−0.0001 (7)	−0.0011 (6)
C5B	0.0189 (8)	0.0185 (7)	0.0167 (7)	0.0014 (7)	0.0005 (6)	0.0007 (6)
C6B	0.0171 (9)	0.0157 (7)	0.0166 (8)	0.0021 (6)	−0.0024 (6)	−0.0007 (6)
C7B	0.0171 (8)	0.0192 (7)	0.0163 (7)	0.0002 (7)	−0.0012 (6)	−0.0005 (6)
C8B	0.0167 (7)	0.0160 (7)	0.0132 (7)	−0.0022 (6)	0.0009 (5)	0.0009 (6)
C9B	0.0145 (7)	0.0150 (6)	0.0135 (6)	−0.0022 (6)	0.0000 (6)	0.0007 (5)
C10B	0.0143 (7)	0.0139 (6)	0.0157 (6)	−0.0014 (6)	−0.0014 (5)	−0.0005 (5)
C11B	0.0162 (7)	0.0173 (7)	0.0160 (7)	0.0007 (6)	0.0015 (6)	−0.0022 (6)
C12B	0.0172 (8)	0.0146 (6)	0.0245 (8)	0.0023 (6)	−0.0027 (6)	−0.0005 (6)
C13B	0.0213 (7)	0.0173 (6)	0.0160 (7)	−0.0021 (6)	−0.0030 (6)	0.0005 (5)
C14B	0.0255 (8)	0.0221 (7)	0.0139 (6)	0.0036 (7)	0.0012 (6)	0.0000 (6)
C15B	0.0180 (7)	0.0184 (7)	0.0182 (7)	0.0038 (6)	0.0007 (6)	−0.0006 (6)
C16B	0.0285 (9)	0.0212 (7)	0.0148 (7)	−0.0026 (7)	−0.0066 (6)	0.0023 (6)
C17B	0.0236 (8)	0.0190 (7)	0.0159 (7)	0.0002 (7)	−0.0014 (6)	0.0021 (5)
C18B	0.0449 (12)	0.0244 (8)	0.0246 (9)	−0.0040 (8)	−0.0040 (8)	0.0067 (7)
C19B	0.0244 (9)	0.0293 (9)	0.0318 (9)	−0.0033 (7)	0.0007 (8)	0.0004 (8)
C20B	0.0224 (8)	0.0166 (7)	0.0180 (7)	0.0015 (6)	−0.0013 (6)	0.0018 (6)

Br1A—C3A	1.8948 (17)	Br1B—C3B	1.8944 (16)
O1A—C8A	1.2304 (19)	O1B—C8B	1.2349 (18)
N1A—C7A	1.286 (2)	N1B—C7B	1.282 (2)
N1A—N2A	1.3830 (18)	N1B—N2B	1.3868 (18)
N2A—C8A	1.348 (2)	N2B—C8B	1.345 (2)
N2A—H1NA	0.91 (2)	N2B—H1NB	0.770 (19)
C1A—C2A	1.383 (2)	C1B—C2B	1.389 (2)
C1A—C6A	1.405 (3)	C1B—C6B	1.393 (3)
C1A—H1AA	0.93	C1B—H1BA	0.93
C2A—C3A	1.387 (2)	C2B—C3B	1.396 (2)
C2A—H2AA	0.93	C2B—H2BA	0.93
C3A—C4A	1.383 (2)	C3B—C4B	1.386 (2)
C4A—C5A	1.390 (2)	C4B—C5B	1.387 (2)
C4A—H4AA	0.93	C4B—H4BA	0.93
C5A—C6A	1.394 (2)	C5B—C6B	1.403 (2)
C5A—H5AA	0.93	C5B—H5BA	0.93
C6A—C7A	1.463 (2)	C6B—C7B	1.468 (2)
C7A—H7AA	0.93	C7B—H7BA	0.93
C8A—C9A	1.533 (2)	C8B—C9B	1.530 (2)
C9A—C10A	1.526 (2)	C9B—C10B	1.526 (2)
C9A—C20A	1.532 (2)	C9B—C20B	1.531 (2)
C9A—H9AA	0.98	C9B—H9BA	0.98
C10A—C15A	1.393 (2)	C10B—C15B	1.394 (2)
C10A—C11A	1.396 (2)	C10B—C11B	1.400 (2)
C11A—C12A	1.388 (2)	C11B—C12B	1.385 (2)
C11A—H11A	0.93	C11B—H11B	0.93
C12A—C13A	1.394 (2)	C12B—C13B	1.392 (2)
C12A—H12A	0.93	C12B—H12B	0.93
C13A—C14A	1.392 (2)	C13B—C14B	1.393 (2)
C13A—C16A	1.507 (2)	C13B—C16B	1.505 (2)
C14A—C15A	1.390 (2)	C14B—C15B	1.387 (2)
C14A—H14A	0.93	C14B—H14B	0.93
C15A—H15A	0.93	C15B—H15B	0.93
C16A—C17A	1.533 (2)	C16B—C17B	1.537 (2)
C16A—H16A	0.97	C16B—H16C	0.97
C16A—H16B	0.97	C16B—H16D	0.97
C17A—C18A	1.505 (3)	C17B—C19B	1.522 (3)
C17A—C19A	1.532 (2)	C17B—C18B	1.523 (2)
C17A—H17A	0.98	C17B—H17B	0.98
C18A—H18A	0.96	C18B—H18D	0.96
C18A—H18B	0.96	C18B—H18E	0.96
C18A—H18C	0.96	C18B—H18F	0.96
C19A—H19A	0.96	C19B—H19D	0.96
C19A—H19B	0.96	C19B—H19E	0.96
C19A—H19C	0.96	C19B—H19F	0.96
C20A—H20A	0.96	C20B—H20D	0.96
C20A—H20B	0.96	C20B—H20E	0.96
C20A—H20C	0.96	C20B—H20F	0.96
C7A—N1A—N2A	114.27 (13)	C7B—N1B—N2B	114.15 (13)
C8A—N2A—N1A	120.01 (13)	C8B—N2B—N1B	120.36 (13)
C8A—N2A—H1NA	121.9 (14)	C8B—N2B—H1NB	118.0 (16)
N1A—N2A—H1NA	118.1 (14)	N1B—N2B—H1NB	121.7 (16)
C2A—C1A—C6A	120.33 (16)	C2B—C1B—C6B	120.66 (15)
C2A—C1A—H1AA	119.8	C2B—C1B—H1BA	119.7
C6A—C1A—H1AA	119.8	C6B—C1B—H1BA	119.7
C1A—C2A—C3A	119.30 (15)	C1B—C2B—C3B	118.66 (16)
C1A—C2A—H2AA	120.3	C1B—C2B—H2BA	120.7
C3A—C2A—H2AA	120.3	C3B—C2B—H2BA	120.7
C4A—C3A—C2A	121.77 (15)	C4B—C3B—C2B	121.92 (15)
C4A—C3A—Br1A	118.38 (13)	C4B—C3B—Br1B	118.22 (12)
C2A—C3A—Br1A	119.85 (13)	C2B—C3B—Br1B	119.86 (13)
C3A—C4A—C5A	118.49 (16)	C3B—C4B—C5B	118.57 (15)
C3A—C4A—H4AA	120.8	C3B—C4B—H4BA	120.7
C5A—C4A—H4AA	120.8	C5B—C4B—H4BA	120.7
C4A—C5A—C6A	121.17 (16)	C4B—C5B—C6B	120.84 (16)
C4A—C5A—H5AA	119.4	C4B—C5B—H5BA	119.6
C6A—C5A—H5AA	119.4	C6B—C5B—H5BA	119.6
C5A—C6A—C1A	118.87 (15)	C1B—C6B—C5B	119.29 (15)
C5A—C6A—C7A	118.81 (16)	C1B—C6B—C7B	122.62 (15)
C1A—C6A—C7A	122.32 (15)	C5B—C6B—C7B	118.06 (16)
N1A—C7A—C6A	120.87 (16)	N1B—C7B—C6B	120.80 (16)
N1A—C7A—H7AA	119.6	N1B—C7B—H7BA	119.6
C6A—C7A—H7AA	119.6	C6B—C7B—H7BA	119.6
O1A—C8A—N2A	124.37 (16)	O1B—C8B—N2B	123.79 (15)
O1A—C8A—C9A	121.71 (15)	O1B—C8B—C9B	121.70 (15)
N2A—C8A—C9A	113.78 (13)	N2B—C8B—C9B	114.50 (13)
C10A—C9A—C20A	114.55 (13)	C10B—C9B—C8B	107.11 (12)
C10A—C9A—C8A	106.07 (12)	C10B—C9B—C20B	114.91 (13)
C20A—C9A—C8A	110.26 (14)	C8B—C9B—C20B	109.92 (13)
C10A—C9A—H9AA	108.6	C10B—C9B—H9BA	108.2
C20A—C9A—H9AA	108.6	C8B—C9B—H9BA	108.2
C8A—C9A—H9AA	108.6	C20B—C9B—H9BA	108.2
C15A—C10A—C11A	118.25 (14)	C15B—C10B—C11B	118.15 (14)
C15A—C10A—C9A	121.57 (14)	C15B—C10B—C9B	122.14 (13)
C11A—C10A—C9A	120.10 (14)	C11B—C10B—C9B	119.70 (13)
C12A—C11A—C10A	120.65 (15)	C12B—C11B—C10B	120.68 (15)
C12A—C11A—H11A	119.7	C12B—C11B—H11B	119.7
C10A—C11A—H11A	119.7	C10B—C11B—H11B	119.7
C11A—C12A—C13A	121.41 (15)	C11B—C12B—C13B	121.51 (15)
C11A—C12A—H12A	119.3	C11B—C12B—H12B	119.2
C13A—C12A—H12A	119.3	C13B—C12B—H12B	119.2
C14A—C13A—C12A	117.58 (14)	C12B—C13B—C14B	117.42 (14)
C14A—C13A—C16A	121.26 (15)	C12B—C13B—C16B	120.39 (15)
C12A—C13A—C16A	121.16 (15)	C14B—C13B—C16B	122.10 (15)
C15A—C14A—C13A	121.43 (15)	C15B—C14B—C13B	121.77 (15)
C15A—C14A—H14A	119.3	C15B—C14B—H14B	119.1
C13A—C14A—H14A	119.3	C13B—C14B—H14B	119.1
C14A—C15A—C10A	120.65 (15)	C14B—C15B—C10B	120.47 (15)
C14A—C15A—H15A	119.7	C14B—C15B—H15B	119.8
C10A—C15A—H15A	119.7	C10B—C15B—H15B	119.8
C13A—C16A—C17A	116.02 (13)	C13B—C16B—C17B	113.29 (13)
C13A—C16A—H16A	108.3	C13B—C16B—H16C	108.9
C17A—C16A—H16A	108.3	C17B—C16B—H16C	108.9
C13A—C16A—H16B	108.3	C13B—C16B—H16D	108.9
C17A—C16A—H16B	108.3	C17B—C16B—H16D	108.9
H16A—C16A—H16B	107.4	H16C—C16B—H16D	107.7
C18A—C17A—C19A	110.80 (15)	C19B—C17B—C18B	110.54 (15)
C18A—C17A—C16A	112.47 (16)	C19B—C17B—C16B	111.74 (15)
C19A—C17A—C16A	109.00 (14)	C18B—C17B—C16B	110.65 (13)
C18A—C17A—H17A	108.1	C19B—C17B—H17B	107.9
C19A—C17A—H17A	108.1	C18B—C17B—H17B	107.9
C16A—C17A—H17A	108.1	C16B—C17B—H17B	107.9
C17A—C18A—H18A	109.5	C17B—C18B—H18D	109.5
C17A—C18A—H18B	109.5	C17B—C18B—H18E	109.5
H18A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
C17A—C18A—H18C	109.5	C17B—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H18E—C18B—H18F	109.5
C17A—C19A—H19A	109.5	C17B—C19B—H19D	109.5
C17A—C19A—H19B	109.5	C17B—C19B—H19E	109.5
H19A—C19A—H19B	109.5	H19D—C19B—H19E	109.5
C17A—C19A—H19C	109.5	C17B—C19B—H19F	109.5
H19A—C19A—H19C	109.5	H19D—C19B—H19F	109.5
H19B—C19A—H19C	109.5	H19E—C19B—H19F	109.5
C9A—C20A—H20A	109.5	C9B—C20B—H20D	109.5
C9A—C20A—H20B	109.5	C9B—C20B—H20E	109.5
H20A—C20A—H20B	109.5	H20D—C20B—H20E	109.5
C9A—C20A—H20C	109.5	C9B—C20B—H20F	109.5
H20A—C20A—H20C	109.5	H20D—C20B—H20F	109.5
H20B—C20A—H20C	109.5	H20E—C20B—H20F	109.5
C7A—N1A—N2A—C8A	−172.90 (15)	C7B—N1B—N2B—C8B	171.64 (15)
C6A—C1A—C2A—C3A	1.7 (3)	C6B—C1B—C2B—C3B	−0.1 (2)
C1A—C2A—C3A—C4A	−2.0 (3)	C1B—C2B—C3B—C4B	1.5 (2)
C1A—C2A—C3A—Br1A	178.62 (12)	C1B—C2B—C3B—Br1B	−178.25 (12)
C2A—C3A—C4A—C5A	0.3 (3)	C2B—C3B—C4B—C5B	−0.9 (2)
Br1A—C3A—C4A—C5A	179.62 (13)	Br1B—C3B—C4B—C5B	178.82 (12)
C3A—C4A—C5A—C6A	1.8 (3)	C3B—C4B—C5B—C6B	−1.0 (2)
C4A—C5A—C6A—C1A	−2.1 (3)	C2B—C1B—C6B—C5B	−1.7 (2)
C4A—C5A—C6A—C7A	177.39 (16)	C2B—C1B—C6B—C7B	176.39 (15)
C2A—C1A—C6A—C5A	0.3 (3)	C4B—C5B—C6B—C1B	2.3 (2)
C2A—C1A—C6A—C7A	−179.19 (15)	C4B—C5B—C6B—C7B	−175.90 (14)
N2A—N1A—C7A—C6A	−176.44 (13)	N2B—N1B—C7B—C6B	179.61 (13)
C5A—C6A—C7A—N1A	−155.46 (16)	C1B—C6B—C7B—N1B	−20.0 (2)
C1A—C6A—C7A—N1A	24.0 (2)	C5B—C6B—C7B—N1B	158.13 (15)
N1A—N2A—C8A—O1A	5.2 (3)	N1B—N2B—C8B—O1B	−4.2 (3)
N1A—N2A—C8A—C9A	−170.40 (13)	N1B—N2B—C8B—C9B	174.74 (13)
O1A—C8A—C9A—C10A	−82.77 (19)	O1B—C8B—C9B—C10B	82.66 (19)
N2A—C8A—C9A—C10A	93.00 (16)	N2B—C8B—C9B—C10B	−96.26 (16)
O1A—C8A—C9A—C20A	41.8 (2)	O1B—C8B—C9B—C20B	−42.8 (2)
N2A—C8A—C9A—C20A	−142.45 (15)	N2B—C8B—C9B—C20B	138.28 (14)
C8A—C9A—C10A—C11A	−96.54 (17)	C8B—C9B—C10B—C11B	77.53 (17)
C8A—C9A—C10A—C15A	80.18 (18)	C8B—C9B—C10B—C15B	−101.83 (16)
C20A—C9A—C10A—C11A	141.61 (15)	C20B—C9B—C10B—C11B	−160.06 (14)
C20A—C9A—C10A—C15A	−41.7 (2)	C20B—C9B—C10B—C15B	20.6 (2)
C15A—C10A—C11A—C12A	−0.6 (2)	C15B—C10B—C11B—C12B	0.4 (2)
C9A—C10A—C11A—C12A	176.19 (15)	C9B—C10B—C11B—C12B	−178.97 (15)
C10A—C11A—C12A—C13A	−1.1 (2)	C10B—C11B—C12B—C13B	0.4 (2)
C11A—C12A—C13A—C14A	1.9 (2)	C11B—C12B—C13B—C14B	−0.9 (2)
C11A—C12A—C13A—C16A	−178.41 (14)	C11B—C12B—C13B—C16B	175.84 (15)
C12A—C13A—C14A—C15A	−1.0 (2)	C12B—C13B—C14B—C15B	0.6 (2)
C16A—C13A—C14A—C15A	179.36 (15)	C16B—C13B—C14B—C15B	−176.03 (15)
C13A—C14A—C15A—C10A	−0.8 (3)	C13B—C14B—C15B—C10B	0.1 (3)
C11A—C10A—C15A—C14A	1.6 (2)	C11B—C10B—C15B—C14B	−0.7 (2)
C9A—C10A—C15A—C14A	−175.20 (15)	C9B—C10B—C15B—C14B	178.71 (15)
C14A—C13A—C16A—C17A	103.66 (19)	C12B—C13B—C16B—C17B	−72.7 (2)
C12A—C13A—C16A—C17A	−76.0 (2)	C14B—C13B—C16B—C17B	103.90 (18)
C13A—C16A—C17A—C18A	−53.4 (2)	C13B—C16B—C17B—C19B	−60.1 (2)
C13A—C16A—C17A—C19A	−176.68 (15)	C13B—C16B—C17B—C18B	176.24 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H1NA···O1Bi	0.91 (2)	1.97 (2)	2.830 (2)	157 (2)
N2B—H1NB···O1Aii	0.77 (2)	2.11 (2)	2.826 (2)	155 (2)
C7A—H7AA···O1Bi	0.93	2.45	3.241 (2)	143
C7B—H7BA···O1Aii	0.93	2.53	3.307 (3)	141
C20B—H20F···N1A	0.96	2.56	3.494 (2)	164
C12A—H12A···Cg2i	0.93	2.66	3.482 (2)	148
C12B—H12B···Cg1ii	0.93	2.79	3.680 (2)	160

Table 1

Selected torsion angles (°)

C8A—C9A—C10A—C11A	−96.54 (17)
C8A—C9A—C10A—C15A	80.18 (18)
C20A—C9A—C10A—C11A	141.61 (15)
C20A—C9A—C10A—C15A	−41.7 (2)
C8B—C9B—C10B—C11B	77.53 (17)
C8B—C9B—C10B—C15B	−101.83 (16)
C20B—C9B—C10B—C11B	−160.06 (14)
C20B—C9B—C10B—C15B	20.6 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H1NA⋯O1Bi	0.91 (2)	1.97 (2)	2.830 (2)	157 (2)
N2B—H1NB⋯O1Aii	0.77 (2)	2.11 (2)	2.826 (2)	155 (2)
C7A—H7AA⋯O1Bi	0.93	2.45	3.241 (2)	143
C7B—H7BA⋯O1Aii	0.93	2.53	3.307 (3)	141
C20B—H20F⋯N1A	0.96	2.56	3.494 (2)	164
C12A—H12A⋯Cg2i	0.93	2.66	3.482 (2)	148
C12B—H12B⋯Cg1ii	0.93	2.79	3.680 (2)	160

Symmetry codes: (i) ; (ii) . Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B benzene rings, respectively.