4-Bromo-N,N′-di­phenyl­benzimidamide N′-oxide

The title compound, C₁₉H₁₅BrN₂O, crystallizes with two similar mol­ecules in the asymmetric unit. The extended structure features dimers linked by pairs of N—H...O and C—H...O hydrogen bonds. The HNCNO moiety of the title compound shows delocalization over the N—C—N part, as evidenced by the similar C—N bond distances.

Computing details

4-Bromo-N,N'-diphenylbenzimidamide N'-oxide

Crystal data

C19H15BrN2O	Dx = 1.500 Mg m^−3
Mr = 367.24	Ga Kα radiation, λ = 1.34139 Å
Orthorhombic, Pna21	Cell parameters from 9781 reflections
a = 17.7036 (16) Å	θ = 4.5–54.4°
b = 5.8468 (6) Å	µ = 2.30 mm^−1
c = 31.418 (3) Å	T = 150 K
V = 3252.0 (5) Å^3	Needle, clear light colourless
Z = 8	0.19 × 0.03 × 0.03 mm
F(000) = 1488

Data collection

Bruker Venture Metaljet diffractometer	6071 independent reflections
Radiation source: Metal Jet, Gallium Liquid Metal Jet Source	4793 reflections with I > 2σ(I)
Helios MX Mirror Optics monochromator	Rint = 0.090
Detector resolution: 10.42 pixels mm^-1	θmax = 54.9°, θmin = 2.5°
ω and φ scans	h = −21→21
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −6→7
Tmin = 0.079, Tmax = 0.201	l = −38→37
100504 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.055	w = 1/[σ^2(Fo^2) + (0.0728P)^2 + 6.1028P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.158	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 1.13 e Å^−3
6071 reflections	Δρmin = −0.64 e Å^−3
416 parameters	Absolute structure: Refined as an inversion twin.
1 restraint	Absolute structure parameter: 0.23 (6)
Primary atom site location: dual

Special details

Experimental. X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Venture diffractometer equipped with a Photon III CMOS Detector, a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.

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. Refined as a 2-component inversion twin.

Hydrogen atoms attached to nitrogen were first located from Fourier difference map then refined using the equivalent calculated positions. The C-bound H atoms were geometrically placed and refined as riding atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1A	0.61038 (7)	0.6881 (3)	0.25148 (3)	0.0760 (4)
O1A	0.4180 (4)	0.7299 (11)	0.4878 (2)	0.0500 (18)
N1A	0.4538 (4)	0.7506 (11)	0.4507 (3)	0.0344 (17)
C1A	0.4319 (4)	0.6209 (13)	0.4185 (3)	0.0351 (18)
N2A	0.3778 (4)	0.4681 (13)	0.4271 (2)	0.0417 (17)
H2A	0.363970	0.461329	0.453973	0.050*
C3A	0.4695 (4)	0.6315 (15)	0.3761 (3)	0.0369 (18)
C4A	0.5143 (5)	0.4453 (15)	0.3630 (3)	0.0402 (19)
H4A	0.516330	0.310580	0.379883	0.048*
C5A	0.5558 (5)	0.4585 (18)	0.3253 (3)	0.047 (2)
H5A	0.586546	0.334943	0.315994	0.057*
C6A	0.5504 (6)	0.6599 (19)	0.3018 (3)	0.051 (2)
C7A	0.5056 (6)	0.8449 (17)	0.3136 (3)	0.047 (2)
H7A	0.503148	0.978161	0.296394	0.057*
C8A	0.4644 (5)	0.8303 (17)	0.3516 (3)	0.043 (2)
H8A	0.433335	0.953821	0.360476	0.051*
C9A	0.5134 (5)	0.9239 (15)	0.4500 (3)	0.0396 (19)
C10A	0.4990 (5)	1.1212 (15)	0.4729 (3)	0.0380 (19)
H10A	0.451900	1.142036	0.486832	0.046*
C11A	0.5530 (5)	1.2838 (15)	0.4752 (3)	0.040 (2)
H11A	0.543730	1.417141	0.491620	0.048*
C12A	0.6217 (5)	1.2623 (15)	0.4542 (4)	0.042 (2)
H12A	0.658205	1.381271	0.455257	0.051*
C13A	0.6354 (5)	1.0632 (17)	0.4319 (3)	0.048 (2)
H13A	0.682490	1.045000	0.417789	0.057*
C14A	0.5821 (5)	0.8882 (14)	0.4296 (3)	0.0409 (19)
H14A	0.592282	0.750290	0.414638	0.049*
C15A	0.3389 (5)	0.3147 (16)	0.3995 (3)	0.041 (2)
C16A	0.3139 (5)	0.1128 (15)	0.4159 (3)	0.044 (2)
H16A	0.323975	0.076505	0.444787	0.053*
C17A	0.2739 (5)	−0.0410 (16)	0.3908 (3)	0.047 (2)
H17A	0.256372	−0.180680	0.402644	0.056*
C18A	0.2594 (5)	0.0097 (19)	0.3481 (3)	0.052 (3)
H18A	0.233473	−0.096676	0.330491	0.062*
C19A	0.2838 (6)	0.2216 (18)	0.3316 (4)	0.051 (3)
H19A	0.272754	0.260575	0.302911	0.061*
C20A	0.3238 (5)	0.3733 (16)	0.3568 (3)	0.045 (2)
H20A	0.340832	0.514948	0.345548	0.055*
C1B	0.3236 (4)	0.3768 (15)	0.5820 (3)	0.0370 (18)
Br1B	0.14367 (7)	0.2681 (2)	0.74742 (3)	0.0701 (4)
N1B	0.3017 (4)	0.2490 (11)	0.5494 (3)	0.0336 (17)
O1B	0.3366 (4)	0.2703 (11)	0.5123 (2)	0.0478 (17)
N2B	0.3789 (4)	0.5326 (12)	0.5731 (2)	0.0417 (17)
H2B	0.393219	0.539951	0.546301	0.050*
C3B	0.2863 (5)	0.3580 (16)	0.6241 (3)	0.0387 (19)
C4B	0.2924 (5)	0.1630 (16)	0.6482 (3)	0.0391 (19)
H4B	0.325401	0.044035	0.639406	0.047*
C5B	0.2506 (5)	0.1381 (18)	0.6856 (3)	0.048 (2)
H5B	0.254569	0.001873	0.701917	0.058*
C6B	0.2046 (6)	0.3074 (19)	0.6984 (3)	0.048 (2)
C7B	0.1990 (5)	0.5162 (18)	0.6760 (3)	0.050 (2)
H7B	0.167883	0.637004	0.686058	0.060*
C8B	0.2411 (5)	0.5390 (16)	0.6382 (3)	0.041 (2)
H8B	0.238858	0.677153	0.622357	0.049*
C9B	0.2439 (5)	0.0776 (15)	0.5503 (3)	0.0393 (19)
C10B	0.2578 (5)	−0.1214 (15)	0.5272 (3)	0.040 (2)
H10B	0.304907	−0.142167	0.513284	0.049*
C11B	0.2031 (6)	−0.2875 (16)	0.5248 (3)	0.042 (2)
H11B	0.212594	−0.422652	0.508851	0.051*
C12B	0.1340 (5)	−0.2606 (14)	0.5453 (4)	0.041 (2)
H12B	0.096363	−0.376087	0.543340	0.049*
C13B	0.1207 (5)	−0.0633 (17)	0.5685 (3)	0.042 (2)
H13B	0.074096	−0.045649	0.583136	0.051*
C14B	0.1746 (5)	0.1094 (15)	0.5707 (3)	0.0401 (19)
H14B	0.164413	0.246787	0.585759	0.048*
C15B	0.4160 (5)	0.6836 (15)	0.6013 (3)	0.040 (2)
C16B	0.4421 (4)	0.8874 (15)	0.5840 (3)	0.041 (2)
H16B	0.433158	0.921877	0.554880	0.050*
C17B	0.4814 (5)	1.0404 (17)	0.6097 (3)	0.049 (2)
H17B	0.498950	1.180375	0.597936	0.059*
C18B	0.4953 (5)	0.9913 (18)	0.6523 (4)	0.054 (3)
H18B	0.521577	1.097190	0.669808	0.065*
C19B	0.4695 (6)	0.7814 (18)	0.6691 (5)	0.053 (3)
H19B	0.479286	0.744164	0.698056	0.063*
C20B	0.4308 (5)	0.6319 (17)	0.6440 (3)	0.046 (2)
H20B	0.413583	0.491091	0.655569	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1A	0.0716 (8)	0.1182 (10)	0.0382 (7)	−0.0140 (7)	0.0150 (7)	0.0000 (9)
O1A	0.060 (4)	0.053 (4)	0.038 (4)	−0.010 (3)	0.018 (3)	−0.007 (3)
N1A	0.040 (4)	0.032 (4)	0.031 (5)	−0.006 (3)	0.006 (4)	−0.006 (3)
C1A	0.039 (4)	0.026 (4)	0.040 (5)	−0.002 (3)	0.003 (3)	0.002 (3)
N2A	0.045 (4)	0.044 (4)	0.036 (4)	−0.005 (3)	0.004 (3)	−0.004 (3)
C3A	0.037 (4)	0.036 (4)	0.037 (5)	−0.002 (4)	0.002 (4)	0.000 (4)
C4A	0.042 (5)	0.040 (5)	0.038 (4)	0.000 (4)	−0.001 (4)	−0.004 (4)
C5A	0.048 (5)	0.055 (6)	0.039 (5)	−0.005 (4)	0.003 (4)	−0.004 (4)
C6A	0.046 (5)	0.069 (7)	0.037 (5)	−0.012 (5)	−0.003 (4)	−0.003 (5)
C7A	0.057 (6)	0.040 (5)	0.046 (6)	−0.007 (5)	−0.015 (5)	0.001 (4)
C8A	0.038 (4)	0.047 (5)	0.043 (6)	0.001 (4)	−0.001 (4)	0.001 (4)
C9A	0.038 (4)	0.041 (5)	0.039 (4)	−0.002 (4)	−0.007 (4)	0.005 (4)
C10A	0.039 (4)	0.045 (5)	0.031 (4)	0.004 (4)	−0.002 (3)	0.001 (4)
C11A	0.049 (5)	0.043 (5)	0.028 (5)	0.002 (4)	−0.007 (4)	0.002 (4)
C12A	0.047 (5)	0.036 (5)	0.045 (6)	−0.005 (4)	−0.008 (4)	0.001 (4)
C13A	0.042 (5)	0.051 (6)	0.050 (6)	−0.002 (4)	−0.003 (4)	0.002 (5)
C14A	0.043 (5)	0.032 (4)	0.048 (5)	0.001 (4)	−0.003 (4)	−0.002 (4)
C15A	0.034 (4)	0.050 (5)	0.039 (5)	−0.001 (4)	0.005 (4)	−0.005 (4)
C16A	0.046 (5)	0.039 (5)	0.048 (5)	−0.004 (4)	−0.001 (4)	−0.005 (4)
C17A	0.050 (5)	0.032 (5)	0.059 (6)	−0.003 (4)	0.003 (4)	−0.002 (4)
C18A	0.049 (5)	0.049 (6)	0.057 (6)	−0.008 (5)	−0.010 (4)	−0.012 (5)
C19A	0.052 (6)	0.063 (7)	0.037 (7)	−0.005 (5)	−0.008 (4)	−0.007 (5)
C20A	0.043 (5)	0.045 (5)	0.049 (5)	−0.002 (4)	−0.003 (4)	−0.001 (4)
C1B	0.036 (4)	0.041 (5)	0.034 (4)	0.002 (4)	0.003 (3)	0.000 (4)
Br1B	0.0672 (7)	0.1061 (9)	0.0369 (6)	−0.0024 (6)	0.0184 (6)	0.0002 (7)
N1B	0.041 (4)	0.032 (4)	0.028 (5)	−0.001 (3)	0.004 (3)	−0.004 (3)
O1B	0.053 (4)	0.051 (4)	0.040 (4)	−0.004 (3)	0.010 (3)	−0.002 (3)
N2B	0.046 (4)	0.038 (4)	0.041 (4)	−0.007 (3)	0.006 (3)	−0.001 (3)
C3B	0.033 (4)	0.045 (5)	0.037 (5)	0.001 (4)	−0.001 (3)	0.001 (4)
C4B	0.038 (4)	0.041 (5)	0.038 (5)	−0.003 (4)	0.001 (4)	0.001 (4)
C5B	0.046 (5)	0.061 (6)	0.036 (5)	−0.013 (5)	−0.010 (4)	0.008 (4)
C6B	0.057 (6)	0.063 (6)	0.024 (5)	−0.002 (5)	−0.001 (4)	−0.007 (4)
C7B	0.041 (5)	0.066 (6)	0.043 (5)	0.006 (4)	0.005 (4)	−0.021 (5)
C8B	0.043 (5)	0.039 (5)	0.040 (5)	0.002 (4)	0.004 (4)	−0.002 (4)
C9B	0.043 (5)	0.039 (5)	0.035 (4)	0.000 (4)	0.004 (4)	0.000 (4)
C10B	0.046 (5)	0.040 (5)	0.036 (4)	0.003 (4)	−0.004 (4)	−0.005 (4)
C11B	0.053 (6)	0.037 (5)	0.037 (6)	−0.004 (4)	−0.005 (4)	−0.004 (4)
C12B	0.043 (5)	0.040 (5)	0.040 (6)	−0.005 (4)	−0.005 (4)	−0.002 (4)
C13B	0.036 (4)	0.044 (6)	0.047 (5)	0.003 (4)	−0.003 (4)	−0.003 (4)
C14B	0.037 (4)	0.042 (5)	0.041 (4)	0.001 (4)	0.004 (4)	−0.003 (4)
C15B	0.037 (5)	0.041 (5)	0.042 (5)	−0.005 (4)	−0.003 (4)	0.000 (4)
C16B	0.036 (4)	0.044 (5)	0.044 (5)	0.003 (4)	0.006 (4)	−0.007 (4)
C17B	0.048 (5)	0.044 (5)	0.054 (6)	−0.002 (4)	0.009 (4)	0.001 (5)
C18B	0.042 (5)	0.051 (6)	0.070 (7)	−0.008 (4)	−0.004 (5)	−0.011 (5)
C19B	0.052 (6)	0.057 (7)	0.048 (7)	−0.004 (5)	−0.007 (5)	−0.005 (5)
C20B	0.039 (5)	0.052 (6)	0.046 (5)	−0.001 (4)	0.002 (4)	0.004 (4)

Geometric parameters (Å, º)

Br1A—C6A	1.911 (10)	C1B—N1B	1.325 (11)
O1A—N1A	1.333 (11)	C1B—N2B	1.366 (11)
N1A—C1A	1.321 (11)	C1B—C3B	1.485 (12)
N1A—C9A	1.463 (11)	Br1B—C6B	1.894 (10)
C1A—N2A	1.338 (11)	N1B—O1B	1.326 (10)
C1A—C3A	1.491 (12)	N1B—C9B	1.433 (11)
N2A—H2A	0.8800	N2B—H2B	0.8800
N2A—C15A	1.423 (12)	N2B—C15B	1.415 (12)
C3A—C4A	1.408 (12)	C3B—C4B	1.373 (14)
C3A—C8A	1.398 (14)	C3B—C8B	1.398 (13)
C4A—H4A	0.9500	C4B—H4B	0.9500
C4A—C5A	1.397 (13)	C4B—C5B	1.396 (13)
C5A—H5A	0.9500	C5B—H5B	0.9500
C5A—C6A	1.393 (15)	C5B—C6B	1.343 (15)
C6A—C7A	1.392 (15)	C6B—C7B	1.413 (15)
C7A—H7A	0.9500	C7B—H7B	0.9500
C7A—C8A	1.400 (14)	C7B—C8B	1.407 (13)
C8A—H8A	0.9500	C8B—H8B	0.9500
C9A—C10A	1.383 (12)	C9B—C10B	1.393 (12)
C9A—C14A	1.391 (12)	C9B—C14B	1.396 (12)
C10A—H10A	0.9500	C10B—H10B	0.9500
C10A—C11A	1.350 (13)	C10B—C11B	1.374 (13)
C11A—H11A	0.9500	C11B—H11B	0.9500
C11A—C12A	1.387 (14)	C11B—C12B	1.392 (14)
C12A—H12A	0.9500	C12B—H12B	0.9500
C12A—C13A	1.381 (14)	C12B—C13B	1.385 (14)
C13A—H13A	0.9500	C13B—H13B	0.9500
C13A—C14A	1.394 (13)	C13B—C14B	1.391 (13)
C14A—H14A	0.9500	C14B—H14B	0.9500
C15A—C16A	1.361 (13)	C15B—C16B	1.389 (13)
C15A—C20A	1.410 (13)	C15B—C20B	1.398 (13)
C16A—H16A	0.9500	C16B—H16B	0.9500
C16A—C17A	1.391 (13)	C16B—C17B	1.391 (13)
C17A—H17A	0.9500	C17B—H17B	0.9500
C17A—C18A	1.397 (15)	C17B—C18B	1.393 (15)
C18A—H18A	0.9500	C18B—H18B	0.9500
C18A—C19A	1.412 (16)	C18B—C19B	1.411 (15)
C19A—H19A	0.9500	C19B—H19B	0.9500
C19A—C20A	1.384 (14)	C19B—C20B	1.364 (15)
C20A—H20A	0.9500	C20B—H20B	0.9500
O1A—N1A—C9A	114.7 (7)	N1B—C1B—N2B	115.3 (7)
C1A—N1A—O1A	118.6 (7)	N1B—C1B—C3B	121.2 (8)
C1A—N1A—C9A	126.7 (8)	N2B—C1B—C3B	123.4 (7)
N1A—C1A—N2A	116.1 (7)	C1B—N1B—O1B	119.3 (7)
N1A—C1A—C3A	121.9 (7)	C1B—N1B—C9B	126.0 (8)
N2A—C1A—C3A	121.8 (7)	O1B—N1B—C9B	114.6 (7)
C1A—N2A—H2A	114.9	C1B—N2B—H2B	115.8
C1A—N2A—C15A	130.1 (8)	C1B—N2B—C15B	128.4 (7)
C15A—N2A—H2A	114.9	C15B—N2B—H2B	115.8
C4A—C3A—C1A	118.7 (8)	C4B—C3B—C1B	121.2 (8)
C8A—C3A—C1A	119.9 (8)	C4B—C3B—C8B	119.9 (9)
C8A—C3A—C4A	121.2 (9)	C8B—C3B—C1B	118.8 (8)
C3A—C4A—H4A	120.0	C3B—C4B—H4B	119.7
C5A—C4A—C3A	120.1 (9)	C3B—C4B—C5B	120.6 (9)
C5A—C4A—H4A	120.0	C5B—C4B—H4B	119.7
C4A—C5A—H5A	121.3	C4B—C5B—H5B	120.1
C6A—C5A—C4A	117.4 (9)	C6B—C5B—C4B	119.8 (9)
C6A—C5A—H5A	121.3	C6B—C5B—H5B	120.1
C5A—C6A—Br1A	118.2 (8)	C5B—C6B—Br1B	119.9 (8)
C5A—C6A—C7A	123.7 (10)	C5B—C6B—C7B	122.0 (9)
C7A—C6A—Br1A	118.1 (8)	C7B—C6B—Br1B	118.0 (7)
C6A—C7A—H7A	120.7	C6B—C7B—H7B	121.2
C6A—C7A—C8A	118.5 (9)	C8B—C7B—C6B	117.7 (9)
C8A—C7A—H7A	120.7	C8B—C7B—H7B	121.2
C3A—C8A—C7A	119.1 (9)	C3B—C8B—C7B	119.9 (9)
C3A—C8A—H8A	120.4	C3B—C8B—H8B	120.1
C7A—C8A—H8A	120.4	C7B—C8B—H8B	120.1
C10A—C9A—N1A	116.0 (7)	C10B—C9B—N1B	116.6 (7)
C10A—C9A—C14A	121.7 (8)	C10B—C9B—C14B	120.3 (8)
C14A—C9A—N1A	122.2 (8)	C14B—C9B—N1B	122.9 (8)
C9A—C10A—H10A	120.5	C9B—C10B—H10B	120.1
C11A—C10A—C9A	119.0 (8)	C11B—C10B—C9B	119.7 (8)
C11A—C10A—H10A	120.5	C11B—C10B—H10B	120.1
C10A—C11A—H11A	118.9	C10B—C11B—H11B	119.5
C10A—C11A—C12A	122.1 (9)	C10B—C11B—C12B	120.9 (9)
C12A—C11A—H11A	118.9	C12B—C11B—H11B	119.5
C11A—C12A—H12A	120.9	C11B—C12B—H12B	120.4
C13A—C12A—C11A	118.1 (9)	C13B—C12B—C11B	119.1 (8)
C13A—C12A—H12A	120.9	C13B—C12B—H12B	120.4
C12A—C13A—H13A	119.1	C12B—C13B—H13B	119.5
C12A—C13A—C14A	121.8 (9)	C12B—C13B—C14B	120.9 (9)
C14A—C13A—H13A	119.1	C14B—C13B—H13B	119.5
C9A—C14A—C13A	117.2 (8)	C9B—C14B—H14B	120.5
C9A—C14A—H14A	121.4	C13B—C14B—C9B	118.9 (8)
C13A—C14A—H14A	121.4	C13B—C14B—H14B	120.5
C16A—C15A—N2A	118.3 (9)	C16B—C15B—N2B	116.3 (8)
C16A—C15A—C20A	120.5 (9)	C16B—C15B—C20B	120.0 (9)
C20A—C15A—N2A	121.2 (8)	C20B—C15B—N2B	123.6 (8)
C15A—C16A—H16A	119.6	C15B—C16B—H16B	120.3
C15A—C16A—C17A	120.9 (9)	C15B—C16B—C17B	119.4 (9)
C17A—C16A—H16A	119.6	C17B—C16B—H16B	120.3
C16A—C17A—H17A	120.0	C16B—C17B—H17B	119.5
C16A—C17A—C18A	120.1 (9)	C16B—C17B—C18B	120.9 (9)
C18A—C17A—H17A	120.0	C18B—C17B—H17B	119.5
C17A—C18A—H18A	120.6	C17B—C18B—H18B	120.6
C17A—C18A—C19A	118.8 (9)	C17B—C18B—C19B	118.9 (10)
C19A—C18A—H18A	120.6	C19B—C18B—H18B	120.6
C18A—C19A—H19A	119.7	C18B—C19B—H19B	119.9
C20A—C19A—C18A	120.6 (11)	C20B—C19B—C18B	120.2 (12)
C20A—C19A—H19A	119.7	C20B—C19B—H19B	119.9
C15A—C20A—H20A	120.4	C15B—C20B—H20B	119.7
C19A—C20A—C15A	119.1 (10)	C19B—C20B—C15B	120.7 (10)
C19A—C20A—H20A	120.4	C19B—C20B—H20B	119.7
Br1A—C6A—C7A—C8A	−176.9 (7)	C1B—N1B—C9B—C10B	−140.5 (9)
O1A—N1A—C1A—N2A	−3.9 (12)	C1B—N1B—C9B—C14B	43.6 (13)
O1A—N1A—C1A—C3A	−179.3 (8)	C1B—N2B—C15B—C16B	−151.1 (8)
O1A—N1A—C9A—C10A	−37.2 (11)	C1B—N2B—C15B—C20B	32.5 (14)
O1A—N1A—C9A—C14A	139.3 (8)	C1B—C3B—C4B—C5B	−173.1 (8)
N1A—C1A—N2A—C15A	175.7 (8)	C1B—C3B—C8B—C7B	173.5 (8)
N1A—C1A—C3A—C4A	109.5 (9)	Br1B—C6B—C7B—C8B	−176.4 (7)
N1A—C1A—C3A—C8A	−65.9 (11)	N1B—C1B—N2B—C15B	−176.6 (8)
N1A—C9A—C10A—C11A	177.1 (8)	N1B—C1B—C3B—C4B	66.9 (11)
N1A—C9A—C14A—C13A	−178.4 (8)	N1B—C1B—C3B—C8B	−109.9 (10)
C1A—N1A—C9A—C10A	141.1 (9)	N1B—C9B—C10B—C11B	−176.4 (8)
C1A—N1A—C9A—C14A	−42.3 (13)	N1B—C9B—C14B—C13B	177.5 (8)
C1A—N2A—C15A—C16A	149.9 (9)	O1B—N1B—C9B—C10B	37.1 (11)
C1A—N2A—C15A—C20A	−32.7 (14)	O1B—N1B—C9B—C14B	−138.8 (8)
C1A—C3A—C4A—C5A	−174.1 (8)	N2B—C1B—N1B—O1B	3.9 (11)
C1A—C3A—C8A—C7A	174.2 (8)	N2B—C1B—N1B—C9B	−178.6 (8)
N2A—C1A—C3A—C4A	−65.7 (11)	N2B—C1B—C3B—C4B	−117.0 (10)
N2A—C1A—C3A—C8A	119.0 (9)	N2B—C1B—C3B—C8B	66.2 (11)
N2A—C15A—C16A—C17A	178.3 (8)	N2B—C15B—C16B—C17B	−177.9 (8)
N2A—C15A—C20A—C19A	−178.0 (9)	N2B—C15B—C20B—C19B	177.4 (9)
C3A—C1A—N2A—C15A	−8.9 (14)	C3B—C1B—N1B—O1B	−179.8 (7)
C3A—C4A—C5A—C6A	−0.3 (13)	C3B—C1B—N1B—C9B	−2.3 (13)
C4A—C3A—C8A—C7A	−1.0 (13)	C3B—C1B—N2B—C15B	7.1 (14)
C4A—C5A—C6A—Br1A	177.0 (7)	C3B—C4B—C5B—C6B	−0.8 (14)
C4A—C5A—C6A—C7A	−0.8 (14)	C4B—C3B—C8B—C7B	−3.3 (13)
C5A—C6A—C7A—C8A	0.9 (14)	C4B—C5B—C6B—Br1B	176.7 (7)
C6A—C7A—C8A—C3A	0.0 (13)	C4B—C5B—C6B—C7B	−2.4 (14)
C8A—C3A—C4A—C5A	1.2 (13)	C5B—C6B—C7B—C8B	2.7 (14)
C9A—N1A—C1A—N2A	177.8 (8)	C6B—C7B—C8B—C3B	0.2 (13)
C9A—N1A—C1A—C3A	2.4 (13)	C8B—C3B—C4B—C5B	3.7 (13)
C9A—C10A—C11A—C12A	1.9 (14)	C9B—C10B—C11B—C12B	−0.4 (15)
C10A—C9A—C14A—C13A	−2.0 (13)	C10B—C9B—C14B—C13B	1.7 (13)
C10A—C11A—C12A—C13A	−2.6 (15)	C10B—C11B—C12B—C13B	−0.2 (16)
C11A—C12A—C13A—C14A	0.9 (15)	C11B—C12B—C13B—C14B	1.6 (15)
C12A—C13A—C14A—C9A	1.3 (14)	C12B—C13B—C14B—C9B	−2.4 (14)
C14A—C9A—C10A—C11A	0.5 (13)	C14B—C9B—C10B—C11B	−0.3 (13)
C15A—C16A—C17A—C18A	0.6 (14)	C15B—C16B—C17B—C18B	0.4 (13)
C16A—C15A—C20A—C19A	−0.6 (14)	C16B—C15B—C20B—C19B	1.1 (14)
C16A—C17A—C18A—C19A	−2.1 (14)	C16B—C17B—C18B—C19B	0.8 (14)
C17A—C18A—C19A—C20A	2.2 (15)	C17B—C18B—C19B—C20B	−1.0 (15)
C18A—C19A—C20A—C15A	−0.9 (15)	C18B—C19B—C20B—C15B	0.1 (15)
C20A—C15A—C16A—C17A	0.8 (14)	C20B—C15B—C16B—C17B	−1.3 (13)

Hydrogen-bond geometry (Å, º)

Cg2, Cg3, Cg5 and Cg6 are the centroids of the C9A–C14A, C15A–C20A, C9B–C14B and C15B–C20B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A···O1B	0.88	2.20	3.005 (11)	152
C10A—H10A···O1B^i	0.95	2.32	3.249 (12)	167
C16A—H16A···O1B	0.95	2.41	3.191 (12)	139
N2B—H2B···O1A	0.88	2.19	2.999 (10)	152
C10B—H10B···O1A^ii	0.95	2.28	3.214 (12)	167
C16B—H16B···O1A	0.95	2.40	3.188 (12)	140
C4A—H4A···Cg2^ii	0.95	2.77	3.614 (10)	149
C4B—H4B···Cg6^ii	0.95	2.64	3.534 (10)	157
C8A—H8A···Cg3^i	0.95	2.71	3.591 (10)	154
C8B—H8B···Cg5^i	0.95	2.85	3.688 (10)	148

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.