6-(4-Bromo-phen-yl)-2-eth-oxy-4-(2,4,6-trimethoxy-phen-yl)nicotinonitrile.

In the asymmetric unit of the title nicotinonitrile derivative, C(23)H(21)BrN(2)O(4), there are two non-planar independent mol-ecules. The central pyridine ring makes dihedral angles of 9.05 (7) and 77.06 (7)°, respectively, with the 4-bromo-phenyl and 2,4,6-trimethoxy-phenyl rings in one mol-ecule, whereas the corresponding values are 5.96 (7) and 82.37 (7)° in the other. All the three meth-oxy groups are essentially in the plane of the attached benzene ring [C-O-C-C angles = 2.99 (19), 4.8 (2) and -6.2 (2)° in one mol-ecule, and 2.69 (18), 176.73 (15) and 1.3 (2)° in the other]. The eth-oxy group is slightly twisted in one mol-ecule [C-C-O-C = 173.84 (12)°], whereas it is coplanar with the pyridine ring in the other [C-C-O-C = -177.23 (13)°]. Weak intra-molecular C-H⋯N inter-actions generate S(5) ring motifs. In the crystal structure, the mol-ecules are linked by weak inter-molecular C-H⋯N and C-H⋯O inter-actions into a supra-molecular three-dimensional network in such a way that the nicotinonitrile units of neighboring mol-ecules are stacked in an anti-parallel manner along the c axis. The crystal is further stabilized by C-H⋯π inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the synthesis and applications of nicotinonitrile derivatives, see: Abdel-Aziz (2007 ▶); Borgna et al. (1993 ▶); Chantrapromma et al. (2009 ▶); Goda et al. (2004 ▶); Raghukumar et al. (2003 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C23H21BrN2O4

M = 469.32

Monoclinic,

a = 14.1799 (2) Å

b = 18.0877 (3) Å

c = 16.6881 (2) Å

β = 95.081 (1)°

V = 4263.38 (11) Å3

Z = 8

Mo Kα radiation

μ = 1.96 mm−1

T = 100 K

0.51 × 0.49 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.437, T max = 0.669

85168 measured reflections

18727 independent reflections

12072 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.095

S = 1.01

18727 reflections

549 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.45 e Å−3

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/S1600536809043943/is2473sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043943/is2473Isup2.hkl

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

C23H21BrN2O4	F(000) = 1920
Mr = 469.32	Dx = 1.462 Mg m−3
Monoclinic, P21/c	Melting point = 423–424 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.1799 (2) Å	Cell parameters from 18727 reflections
b = 18.0877 (3) Å	θ = 2.1–35.0°
c = 16.6881 (2) Å	µ = 1.96 mm−1
β = 95.081 (1)°	T = 100 K
V = 4263.38 (11) Å3	Block, colorless
Z = 8	0.51 × 0.49 × 0.22 mm

Bruker APEXII CCD area-detector diffractometer	18727 independent reflections
Radiation source: sealed tube	12072 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 35.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −22→22
Tmin = 0.437, Tmax = 0.669	k = −29→27
85168 measured reflections	l = −26→25

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0378P)2 + 1.2763P] where P = (Fo2 + 2Fc2)/3
18727 reflections	(Δ/σ)max = 0.003
549 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

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

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	0.415133 (12)	0.399816 (9)	0.519413 (10)	0.02931 (5)
O1A	0.93118 (7)	0.24881 (5)	0.28179 (6)	0.0205 (2)
O2A	0.88259 (7)	0.02891 (5)	0.50720 (6)	0.01749 (19)
O3A	0.79300 (9)	−0.21035 (6)	0.41508 (6)	0.0279 (2)
O4A	0.74715 (8)	0.00621 (5)	0.24317 (6)	0.0216 (2)
N1A	0.79667 (8)	0.25126 (6)	0.35033 (7)	0.0163 (2)
N2A	0.99990 (10)	0.06683 (8)	0.24974 (8)	0.0274 (3)
C1A	0.64576 (11)	0.33207 (8)	0.40150 (9)	0.0213 (3)
H1AA	0.6868	0.3535	0.3677	0.026*
C2A	0.57443 (11)	0.37470 (8)	0.42979 (10)	0.0244 (3)
H2AA	0.5670	0.4240	0.4146	0.029*
C3A	0.51453 (10)	0.34262 (8)	0.48100 (9)	0.0212 (3)
C4A	0.52353 (10)	0.26904 (8)	0.50332 (9)	0.0210 (3)
H4AA	0.4827	0.2483	0.5377	0.025*
C5A	0.59440 (10)	0.22651 (8)	0.47372 (8)	0.0186 (3)
H5AA	0.6002	0.1769	0.4878	0.022*
C6A	0.65723 (10)	0.25764 (7)	0.42278 (8)	0.0166 (2)
C7A	0.73374 (10)	0.21320 (7)	0.39098 (8)	0.0153 (2)
C8A	0.74013 (10)	0.13710 (7)	0.40206 (8)	0.0163 (2)
H8AA	0.6982	0.1130	0.4330	0.020*
C9A	0.80937 (10)	0.09694 (7)	0.36680 (8)	0.0159 (2)
C10A	0.87236 (10)	0.13553 (7)	0.32258 (8)	0.0166 (2)
C11A	0.86418 (10)	0.21338 (7)	0.31897 (8)	0.0169 (3)
C12A	0.81270 (9)	0.01486 (7)	0.37548 (8)	0.0157 (2)
C13A	0.84560 (10)	−0.01815 (7)	0.44856 (8)	0.0161 (2)
C14A	0.84073 (10)	−0.09404 (7)	0.45904 (9)	0.0181 (3)
H14A	0.8641	−0.1157	0.5073	0.022*
C15A	0.80025 (11)	−0.13720 (7)	0.39600 (9)	0.0199 (3)
C16A	0.76879 (10)	−0.10705 (8)	0.32189 (9)	0.0195 (3)
H16A	0.7434	−0.1367	0.2799	0.023*
C17A	0.77663 (10)	−0.03050 (7)	0.31265 (8)	0.0173 (3)
C18A	0.93260 (11)	0.32872 (8)	0.28667 (9)	0.0208 (3)
H18A	0.9353	0.3446	0.3423	0.025*
H18B	0.8761	0.3493	0.2580	0.025*
C19A	1.01910 (12)	0.35363 (9)	0.24895 (10)	0.0294 (4)
H19A	1.0228	0.4066	0.2506	0.044*
H19B	1.0156	0.3372	0.1941	0.044*
H19C	1.0744	0.3330	0.2780	0.044*
C20A	0.92176 (10)	−0.00406 (8)	0.58126 (8)	0.0194 (3)
H20A	0.9507	0.0336	0.6158	0.029*
H20B	0.9685	−0.0401	0.5700	0.029*
H20C	0.8722	−0.0277	0.6075	0.029*
C21A	0.75721 (18)	−0.25954 (9)	0.35314 (11)	0.0464 (5)
H21A	0.7560	−0.3089	0.3741	0.070*
H21B	0.7973	−0.2580	0.3097	0.070*
H21C	0.6942	−0.2449	0.3338	0.070*
C22A	0.71499 (11)	−0.03616 (8)	0.17402 (9)	0.0233 (3)
H22A	0.6994	−0.0036	0.1294	0.035*
H22B	0.6598	−0.0639	0.1850	0.035*
H22C	0.7641	−0.0695	0.1611	0.035*
C23A	0.94346 (11)	0.09810 (8)	0.28221 (9)	0.0200 (3)
Br1B	1.103317 (12)	0.395272 (9)	0.476239 (10)	0.02990 (5)
O1B	0.57485 (7)	0.27568 (5)	0.71164 (6)	0.0202 (2)
O2B	0.62698 (7)	0.02194 (5)	0.51718 (6)	0.01751 (19)
O3B	0.73304 (9)	−0.19538 (6)	0.66989 (7)	0.0289 (3)
O4B	0.76063 (8)	0.04510 (5)	0.78231 (6)	0.0212 (2)
N1B	0.71233 (8)	0.26852 (6)	0.64794 (7)	0.0165 (2)
N2B	0.47997 (10)	0.09979 (8)	0.73356 (9)	0.0300 (3)
C1B	0.86314 (11)	0.34248 (8)	0.58904 (9)	0.0224 (3)
H1BA	0.8191	0.3678	0.6168	0.027*
C2B	0.93700 (12)	0.38133 (8)	0.55887 (10)	0.0255 (3)
H2BA	0.9428	0.4321	0.5666	0.031*
C3B	1.00145 (11)	0.34315 (8)	0.51734 (9)	0.0211 (3)
C4B	0.99424 (10)	0.26760 (8)	0.50491 (9)	0.0212 (3)
H4BA	1.0382	0.2429	0.4765	0.025*
C5B	0.92041 (10)	0.22931 (8)	0.53546 (9)	0.0197 (3)
H5BA	0.9150	0.1786	0.5274	0.024*
C6B	0.85397 (10)	0.26631 (7)	0.57832 (8)	0.0161 (2)
C7B	0.77575 (9)	0.22614 (7)	0.61271 (8)	0.0154 (2)
C8B	0.76838 (10)	0.14930 (7)	0.61027 (8)	0.0159 (2)
H8BA	0.8128	0.1216	0.5855	0.019*
C9B	0.69472 (10)	0.11389 (7)	0.64472 (8)	0.0152 (2)
C10B	0.62731 (10)	0.15791 (7)	0.67798 (8)	0.0163 (2)
C11B	0.64068 (10)	0.23539 (7)	0.67824 (8)	0.0164 (2)
C12B	0.69364 (9)	0.03151 (7)	0.65008 (8)	0.0156 (2)
C13B	0.66365 (9)	−0.01382 (7)	0.58520 (8)	0.0151 (2)
C14B	0.67260 (10)	−0.09074 (7)	0.58966 (9)	0.0181 (3)
H14B	0.6503	−0.1205	0.5466	0.022*
C15B	0.71545 (11)	−0.12171 (8)	0.65961 (9)	0.0205 (3)
C16B	0.74559 (11)	−0.07822 (7)	0.72598 (9)	0.0194 (3)
H16B	0.7735	−0.0998	0.7728	0.023*
C17B	0.73323 (10)	−0.00229 (7)	0.72081 (8)	0.0165 (3)
C18B	0.58732 (11)	0.35528 (7)	0.71198 (9)	0.0212 (3)
H18C	0.5843	0.3740	0.6574	0.025*
H18D	0.6483	0.3684	0.7392	0.025*
C19B	0.50878 (13)	0.38711 (9)	0.75552 (11)	0.0322 (4)
H19D	0.5140	0.4400	0.7567	0.048*
H19E	0.5130	0.3685	0.8096	0.048*
H19F	0.4490	0.3732	0.7282	0.048*
C20B	0.59292 (10)	−0.02279 (8)	0.44918 (9)	0.0196 (3)
H20D	0.5672	0.0086	0.4063	0.029*
H20E	0.5446	−0.0557	0.4646	0.029*
H20F	0.6443	−0.0511	0.4313	0.029*
C21B	0.70011 (16)	−0.24452 (9)	0.60668 (11)	0.0396 (5)
H21D	0.7188	−0.2941	0.6210	0.059*
H21E	0.7270	−0.2306	0.5581	0.059*
H21F	0.6323	−0.2419	0.5984	0.059*
C22B	0.80585 (12)	0.01372 (9)	0.85449 (9)	0.0252 (3)
H22D	0.8217	0.0523	0.8928	0.038*
H22E	0.8625	−0.0115	0.8425	0.038*
H22F	0.7637	−0.0207	0.8766	0.038*
C23B	0.54596 (11)	0.12606 (8)	0.70986 (9)	0.0203 (3)

	U11	U22	U33	U12	U13	U23
Br1A	0.02877 (9)	0.03090 (8)	0.02875 (9)	0.01345 (6)	0.00520 (6)	−0.00364 (7)
O1A	0.0216 (5)	0.0169 (5)	0.0241 (5)	−0.0004 (4)	0.0076 (4)	0.0033 (4)
O2A	0.0201 (5)	0.0157 (4)	0.0159 (5)	0.0020 (4)	−0.0026 (4)	−0.0004 (4)
O3A	0.0481 (7)	0.0126 (5)	0.0226 (5)	−0.0021 (5)	0.0006 (5)	−0.0012 (4)
O4A	0.0311 (6)	0.0173 (5)	0.0156 (5)	0.0008 (4)	−0.0028 (4)	−0.0009 (4)
N1A	0.0176 (5)	0.0148 (5)	0.0165 (5)	0.0008 (4)	0.0013 (4)	0.0010 (4)
N2A	0.0293 (7)	0.0286 (7)	0.0250 (7)	0.0085 (6)	0.0069 (5)	0.0033 (5)
C1A	0.0248 (7)	0.0159 (6)	0.0235 (7)	0.0014 (5)	0.0039 (6)	0.0008 (5)
C2A	0.0286 (8)	0.0165 (6)	0.0285 (8)	0.0051 (6)	0.0044 (6)	−0.0014 (6)
C3A	0.0199 (7)	0.0230 (7)	0.0202 (7)	0.0063 (5)	−0.0006 (5)	−0.0048 (5)
C4A	0.0194 (7)	0.0254 (7)	0.0183 (7)	0.0040 (5)	0.0020 (5)	0.0016 (5)
C5A	0.0186 (7)	0.0180 (6)	0.0190 (7)	0.0024 (5)	0.0009 (5)	0.0021 (5)
C6A	0.0174 (6)	0.0156 (6)	0.0167 (6)	0.0012 (5)	0.0006 (5)	−0.0002 (5)
C7A	0.0169 (6)	0.0144 (6)	0.0144 (6)	0.0007 (5)	−0.0003 (5)	−0.0002 (5)
C8A	0.0178 (6)	0.0145 (6)	0.0167 (6)	0.0002 (5)	0.0022 (5)	−0.0001 (5)
C9A	0.0171 (6)	0.0137 (6)	0.0165 (6)	0.0012 (5)	−0.0005 (5)	−0.0006 (5)
C10A	0.0170 (6)	0.0170 (6)	0.0158 (6)	0.0022 (5)	0.0013 (5)	0.0008 (5)
C11A	0.0183 (6)	0.0164 (6)	0.0159 (6)	−0.0001 (5)	0.0012 (5)	0.0022 (5)
C12A	0.0160 (6)	0.0133 (6)	0.0181 (6)	0.0009 (5)	0.0028 (5)	−0.0002 (5)
C13A	0.0159 (6)	0.0146 (6)	0.0180 (6)	0.0013 (5)	0.0020 (5)	−0.0028 (5)
C14A	0.0212 (7)	0.0143 (6)	0.0187 (6)	0.0027 (5)	0.0009 (5)	0.0005 (5)
C15A	0.0246 (7)	0.0135 (6)	0.0222 (7)	0.0013 (5)	0.0046 (6)	−0.0011 (5)
C16A	0.0226 (7)	0.0162 (6)	0.0199 (7)	−0.0008 (5)	0.0017 (5)	−0.0049 (5)
C17A	0.0180 (6)	0.0167 (6)	0.0173 (6)	0.0025 (5)	0.0018 (5)	−0.0003 (5)
C18A	0.0240 (7)	0.0164 (6)	0.0221 (7)	−0.0024 (5)	0.0017 (6)	0.0029 (5)
C19A	0.0315 (9)	0.0280 (8)	0.0295 (8)	−0.0077 (7)	0.0068 (7)	0.0046 (7)
C20A	0.0203 (7)	0.0207 (6)	0.0168 (6)	0.0033 (5)	−0.0005 (5)	−0.0003 (5)
C21A	0.0914 (17)	0.0167 (7)	0.0298 (9)	−0.0114 (9)	−0.0025 (10)	−0.0053 (7)
C22A	0.0291 (8)	0.0252 (7)	0.0156 (7)	−0.0035 (6)	0.0007 (6)	−0.0022 (5)
C23A	0.0227 (7)	0.0186 (6)	0.0188 (6)	0.0022 (5)	0.0022 (5)	0.0036 (5)
Br1B	0.03256 (9)	0.03036 (8)	0.02790 (8)	−0.01565 (7)	0.00899 (7)	−0.00084 (6)
O1B	0.0215 (5)	0.0148 (4)	0.0251 (5)	0.0019 (4)	0.0066 (4)	−0.0036 (4)
O2B	0.0203 (5)	0.0152 (4)	0.0164 (5)	0.0000 (4)	−0.0017 (4)	0.0008 (4)
O3B	0.0466 (7)	0.0111 (4)	0.0266 (6)	−0.0007 (4)	−0.0092 (5)	0.0014 (4)
O4B	0.0309 (6)	0.0161 (5)	0.0159 (5)	0.0000 (4)	−0.0021 (4)	−0.0010 (4)
N1B	0.0180 (6)	0.0140 (5)	0.0174 (5)	0.0003 (4)	0.0013 (4)	−0.0017 (4)
N2B	0.0264 (7)	0.0298 (7)	0.0349 (8)	−0.0051 (6)	0.0099 (6)	−0.0027 (6)
C1B	0.0265 (8)	0.0163 (6)	0.0255 (7)	−0.0029 (5)	0.0077 (6)	−0.0017 (5)
C2B	0.0346 (9)	0.0158 (6)	0.0271 (8)	−0.0078 (6)	0.0072 (7)	−0.0023 (6)
C3B	0.0229 (7)	0.0207 (7)	0.0197 (7)	−0.0074 (5)	0.0018 (5)	0.0029 (5)
C4B	0.0198 (7)	0.0203 (7)	0.0238 (7)	−0.0013 (5)	0.0038 (6)	0.0014 (5)
C5B	0.0205 (7)	0.0158 (6)	0.0231 (7)	−0.0005 (5)	0.0031 (5)	0.0015 (5)
C6B	0.0185 (6)	0.0145 (6)	0.0152 (6)	−0.0010 (5)	−0.0001 (5)	0.0012 (5)
C7B	0.0172 (6)	0.0145 (6)	0.0146 (6)	−0.0004 (5)	0.0011 (5)	−0.0002 (5)
C8B	0.0169 (6)	0.0131 (5)	0.0178 (6)	0.0014 (5)	0.0022 (5)	0.0000 (5)
C9B	0.0166 (6)	0.0131 (6)	0.0157 (6)	−0.0002 (4)	0.0004 (5)	0.0009 (5)
C10B	0.0172 (6)	0.0154 (6)	0.0163 (6)	−0.0008 (5)	0.0017 (5)	−0.0005 (5)
C11B	0.0174 (6)	0.0151 (6)	0.0165 (6)	0.0014 (5)	0.0010 (5)	−0.0028 (5)
C12B	0.0163 (6)	0.0120 (5)	0.0189 (6)	−0.0007 (4)	0.0035 (5)	0.0002 (5)
C13B	0.0133 (6)	0.0151 (6)	0.0171 (6)	−0.0005 (4)	0.0022 (5)	0.0013 (5)
C14B	0.0202 (7)	0.0142 (6)	0.0196 (7)	−0.0022 (5)	0.0005 (5)	−0.0004 (5)
C15B	0.0246 (7)	0.0130 (6)	0.0238 (7)	−0.0016 (5)	0.0024 (6)	0.0021 (5)
C16B	0.0251 (7)	0.0146 (6)	0.0182 (6)	−0.0012 (5)	−0.0007 (5)	0.0033 (5)
C17B	0.0185 (6)	0.0141 (6)	0.0171 (6)	−0.0027 (5)	0.0022 (5)	−0.0007 (5)
C18B	0.0252 (7)	0.0143 (6)	0.0241 (7)	0.0021 (5)	0.0015 (6)	−0.0029 (5)
C19B	0.0352 (9)	0.0256 (8)	0.0371 (9)	0.0069 (7)	0.0102 (7)	−0.0078 (7)
C20B	0.0190 (7)	0.0203 (6)	0.0191 (7)	−0.0007 (5)	−0.0010 (5)	−0.0019 (5)
C21B	0.0672 (14)	0.0138 (7)	0.0347 (10)	−0.0012 (8)	−0.0124 (9)	−0.0030 (7)
C22B	0.0341 (9)	0.0239 (7)	0.0168 (7)	0.0015 (6)	−0.0025 (6)	0.0000 (6)
C23B	0.0219 (7)	0.0170 (6)	0.0221 (7)	0.0001 (5)	0.0030 (5)	−0.0034 (5)

Br1A—C3A	1.9047 (14)	Br1B—C3B	1.9029 (14)
O1A—C11A	1.3426 (16)	O1B—C11B	1.3436 (16)
O1A—C18A	1.4478 (17)	O1B—C18B	1.4505 (17)
O2A—C13A	1.3662 (16)	O2B—C13B	1.3684 (16)
O2A—C20A	1.4389 (17)	O2B—C20B	1.4418 (17)
O3A—C15A	1.3668 (17)	O3B—C15B	1.3637 (17)
O3A—C21A	1.423 (2)	O3B—C21B	1.4259 (19)
O4A—C17A	1.3690 (17)	O4B—C17B	1.3669 (16)
O4A—C22A	1.4262 (17)	O4B—C22B	1.4310 (18)
N1A—C11A	1.3223 (17)	N1B—C11B	1.3185 (17)
N1A—C7A	1.3555 (17)	N1B—C7B	1.3550 (17)
N2A—C23A	1.1536 (19)	N2B—C23B	1.1504 (19)
C1A—C2A	1.387 (2)	C1B—C2B	1.392 (2)
C1A—C6A	1.3982 (19)	C1B—C6B	1.3940 (19)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.385 (2)	C2B—C3B	1.380 (2)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.385 (2)	C3B—C4B	1.385 (2)
C4A—C5A	1.3907 (19)	C4B—C5B	1.3894 (19)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.4026 (19)	C5B—C6B	1.4021 (19)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.4856 (19)	C6B—C7B	1.4833 (18)
C7A—C8A	1.3908 (18)	C7B—C8B	1.3942 (18)
C8A—C9A	1.3929 (18)	C8B—C9B	1.3921 (18)
C8A—H8AA	0.9300	C8B—H8BA	0.9300
C9A—C10A	1.3952 (19)	C9B—C10B	1.3962 (18)
C9A—C12A	1.4919 (18)	C9B—C12B	1.4930 (18)
C10A—C11A	1.4137 (19)	C10B—C11B	1.4141 (18)
C10A—C23A	1.4314 (19)	C10B—C23B	1.4333 (19)
C12A—C17A	1.3924 (19)	C12B—C13B	1.3943 (19)
C12A—C13A	1.4002 (19)	C12B—C17B	1.4017 (19)
C13A—C14A	1.3863 (18)	C13B—C14B	1.3985 (18)
C14A—C15A	1.392 (2)	C14B—C15B	1.386 (2)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—C16A	1.389 (2)	C15B—C16B	1.394 (2)
C16A—C17A	1.3987 (19)	C16B—C17B	1.3862 (19)
C16A—H16A	0.9300	C16B—H16B	0.9300
C18A—C19A	1.497 (2)	C18B—C19B	1.498 (2)
C18A—H18A	0.9700	C18B—H18C	0.9700
C18A—H18B	0.9700	C18B—H18D	0.9700
C19A—H19A	0.9600	C19B—H19D	0.9600
C19A—H19B	0.9600	C19B—H19E	0.9600
C19A—H19C	0.9600	C19B—H19F	0.9600
C20A—H20A	0.9600	C20B—H20D	0.9600
C20A—H20B	0.9600	C20B—H20E	0.9600
C20A—H20C	0.9600	C20B—H20F	0.9600
C21A—H21A	0.9600	C21B—H21D	0.9600
C21A—H21B	0.9600	C21B—H21E	0.9600
C21A—H21C	0.9600	C21B—H21F	0.9600
C22A—H22A	0.9600	C22B—H22D	0.9600
C22A—H22B	0.9600	C22B—H22E	0.9600
C22A—H22C	0.9600	C22B—H22F	0.9600
C11A—O1A—C18A	117.22 (11)	C11B—O1B—C18B	116.81 (11)
C13A—O2A—C20A	116.84 (11)	C13B—O2B—C20B	117.63 (10)
C15A—O3A—C21A	117.74 (12)	C15B—O3B—C21B	118.15 (12)
C17A—O4A—C22A	118.45 (11)	C17B—O4B—C22B	117.36 (11)
C11A—N1A—C7A	117.82 (11)	C11B—N1B—C7B	118.22 (11)
C2A—C1A—C6A	121.37 (14)	C2B—C1B—C6B	121.14 (14)
C2A—C1A—H1AA	119.3	C2B—C1B—H1BA	119.4
C6A—C1A—H1AA	119.3	C6B—C1B—H1BA	119.4
C3A—C2A—C1A	118.86 (14)	C3B—C2B—C1B	118.81 (13)
C3A—C2A—H2AA	120.6	C3B—C2B—H2BA	120.6
C1A—C2A—H2AA	120.6	C1B—C2B—H2BA	120.6
C2A—C3A—C4A	121.46 (13)	C2B—C3B—C4B	121.72 (13)
C2A—C3A—Br1A	119.52 (11)	C2B—C3B—Br1B	119.39 (11)
C4A—C3A—Br1A	118.99 (11)	C4B—C3B—Br1B	118.90 (11)
C3A—C4A—C5A	119.23 (13)	C3B—C4B—C5B	119.01 (14)
C3A—C4A—H4AA	120.4	C3B—C4B—H4BA	120.5
C5A—C4A—H4AA	120.4	C5B—C4B—H4BA	120.5
C4A—C5A—C6A	120.73 (13)	C4B—C5B—C6B	120.76 (13)
C4A—C5A—H5AA	119.6	C4B—C5B—H5BA	119.6
C6A—C5A—H5AA	119.6	C6B—C5B—H5BA	119.6
C1A—C6A—C5A	118.34 (13)	C1B—C6B—C5B	118.55 (13)
C1A—C6A—C7A	120.16 (12)	C1B—C6B—C7B	119.93 (12)
C5A—C6A—C7A	121.49 (12)	C5B—C6B—C7B	121.52 (12)
N1A—C7A—C8A	122.09 (12)	N1B—C7B—C8B	121.72 (12)
N1A—C7A—C6A	115.98 (11)	N1B—C7B—C6B	116.01 (11)
C8A—C7A—C6A	121.94 (12)	C8B—C7B—C6B	122.26 (12)
C7A—C8A—C9A	120.00 (12)	C9B—C8B—C7B	120.24 (12)
C7A—C8A—H8AA	120.0	C9B—C8B—H8BA	119.9
C9A—C8A—H8AA	120.0	C7B—C8B—H8BA	119.9
C8A—C9A—C10A	118.08 (12)	C8B—C9B—C10B	117.84 (12)
C8A—C9A—C12A	119.70 (12)	C8B—C9B—C12B	119.73 (12)
C10A—C9A—C12A	122.20 (12)	C10B—C9B—C12B	122.30 (12)
C9A—C10A—C11A	117.83 (12)	C9B—C10B—C11B	118.04 (12)
C9A—C10A—C23A	121.53 (12)	C9B—C10B—C23B	121.34 (12)
C11A—C10A—C23A	120.63 (12)	C11B—C10B—C23B	120.62 (12)
N1A—C11A—O1A	120.15 (12)	N1B—C11B—O1B	119.99 (12)
N1A—C11A—C10A	123.97 (12)	N1B—C11B—C10B	123.84 (12)
O1A—C11A—C10A	115.87 (12)	O1B—C11B—C10B	116.16 (12)
C17A—C12A—C13A	118.45 (12)	C13B—C12B—C17B	117.99 (12)
C17A—C12A—C9A	120.45 (12)	C13B—C12B—C9B	122.99 (12)
C13A—C12A—C9A	120.94 (12)	C17B—C12B—C9B	118.71 (12)
O2A—C13A—C14A	123.15 (13)	O2B—C13B—C12B	115.69 (11)
O2A—C13A—C12A	115.80 (11)	O2B—C13B—C14B	122.72 (12)
C14A—C13A—C12A	121.05 (13)	C12B—C13B—C14B	121.58 (13)
C13A—C14A—C15A	118.79 (13)	C15B—C14B—C13B	118.55 (13)
C13A—C14A—H14A	120.6	C15B—C14B—H14B	120.7
C15A—C14A—H14A	120.6	C13B—C14B—H14B	120.7
O3A—C15A—C16A	124.25 (13)	O3B—C15B—C14B	124.23 (13)
O3A—C15A—C14A	113.65 (13)	O3B—C15B—C16B	114.31 (13)
C16A—C15A—C14A	122.08 (13)	C14B—C15B—C16B	121.46 (13)
C15A—C16A—C17A	117.68 (13)	C17B—C16B—C15B	118.77 (13)
C15A—C16A—H16A	121.2	C17B—C16B—H16B	120.6
C17A—C16A—H16A	121.2	C15B—C16B—H16B	120.6
O4A—C17A—C12A	114.60 (12)	O4B—C17B—C16B	123.28 (13)
O4A—C17A—C16A	123.52 (13)	O4B—C17B—C12B	115.13 (12)
C12A—C17A—C16A	121.85 (13)	C16B—C17B—C12B	121.57 (13)
O1A—C18A—C19A	106.54 (12)	O1B—C18B—C19B	106.73 (12)
O1A—C18A—H18A	110.4	O1B—C18B—H18C	110.4
C19A—C18A—H18A	110.4	C19B—C18B—H18C	110.4
O1A—C18A—H18B	110.4	O1B—C18B—H18D	110.4
C19A—C18A—H18B	110.4	C19B—C18B—H18D	110.4
H18A—C18A—H18B	108.6	H18C—C18B—H18D	108.6
C18A—C19A—H19A	109.5	C18B—C19B—H19D	109.5
C18A—C19A—H19B	109.5	C18B—C19B—H19E	109.5
H19A—C19A—H19B	109.5	H19D—C19B—H19E	109.5
C18A—C19A—H19C	109.5	C18B—C19B—H19F	109.5
H19A—C19A—H19C	109.5	H19D—C19B—H19F	109.5
H19B—C19A—H19C	109.5	H19E—C19B—H19F	109.5
O2A—C20A—H20A	109.5	O2B—C20B—H20D	109.5
O2A—C20A—H20B	109.5	O2B—C20B—H20E	109.5
H20A—C20A—H20B	109.5	H20D—C20B—H20E	109.5
O2A—C20A—H20C	109.5	O2B—C20B—H20F	109.5
H20A—C20A—H20C	109.5	H20D—C20B—H20F	109.5
H20B—C20A—H20C	109.5	H20E—C20B—H20F	109.5
O3A—C21A—H21A	109.5	O3B—C21B—H21D	109.5
O3A—C21A—H21B	109.5	O3B—C21B—H21E	109.5
H21A—C21A—H21B	109.5	H21D—C21B—H21E	109.5
O3A—C21A—H21C	109.5	O3B—C21B—H21F	109.5
H21A—C21A—H21C	109.5	H21D—C21B—H21F	109.5
H21B—C21A—H21C	109.5	H21E—C21B—H21F	109.5
O4A—C22A—H22A	109.5	O4B—C22B—H22D	109.5
O4A—C22A—H22B	109.5	O4B—C22B—H22E	109.5
H22A—C22A—H22B	109.5	H22D—C22B—H22E	109.5
O4A—C22A—H22C	109.5	O4B—C22B—H22F	109.5
H22A—C22A—H22C	109.5	H22D—C22B—H22F	109.5
H22B—C22A—H22C	109.5	H22E—C22B—H22F	109.5
N2A—C23A—C10A	178.83 (16)	N2B—C23B—C10B	178.29 (17)
C6A—C1A—C2A—C3A	0.9 (2)	C6B—C1B—C2B—C3B	0.4 (2)
C1A—C2A—C3A—C4A	−1.0 (2)	C1B—C2B—C3B—C4B	0.2 (2)
C1A—C2A—C3A—Br1A	−179.19 (12)	C1B—C2B—C3B—Br1B	−179.62 (12)
C2A—C3A—C4A—C5A	0.1 (2)	C2B—C3B—C4B—C5B	−0.3 (2)
Br1A—C3A—C4A—C5A	178.29 (11)	Br1B—C3B—C4B—C5B	179.45 (11)
C3A—C4A—C5A—C6A	1.0 (2)	C3B—C4B—C5B—C6B	0.0 (2)
C2A—C1A—C6A—C5A	0.1 (2)	C2B—C1B—C6B—C5B	−0.7 (2)
C2A—C1A—C6A—C7A	179.46 (14)	C2B—C1B—C6B—C7B	178.65 (14)
C4A—C5A—C6A—C1A	−1.1 (2)	C4B—C5B—C6B—C1B	0.5 (2)
C4A—C5A—C6A—C7A	179.61 (13)	C4B—C5B—C6B—C7B	−178.82 (13)
C11A—N1A—C7A—C8A	1.8 (2)	C11B—N1B—C7B—C8B	−2.1 (2)
C11A—N1A—C7A—C6A	−178.00 (12)	C11B—N1B—C7B—C6B	178.93 (12)
C1A—C6A—C7A—N1A	8.23 (19)	C1B—C6B—C7B—N1B	5.09 (19)
C5A—C6A—C7A—N1A	−172.45 (13)	C5B—C6B—C7B—N1B	−175.57 (13)
C1A—C6A—C7A—C8A	−171.55 (13)	C1B—C6B—C7B—C8B	−173.91 (14)
C5A—C6A—C7A—C8A	7.8 (2)	C5B—C6B—C7B—C8B	5.4 (2)
N1A—C7A—C8A—C9A	−3.9 (2)	N1B—C7B—C8B—C9B	−0.2 (2)
C6A—C7A—C8A—C9A	175.86 (13)	C6B—C7B—C8B—C9B	178.75 (13)
C7A—C8A—C9A—C10A	1.6 (2)	C7B—C8B—C9B—C10B	2.8 (2)
C7A—C8A—C9A—C12A	−176.91 (13)	C7B—C8B—C9B—C12B	−173.05 (13)
C8A—C9A—C10A—C11A	2.4 (2)	C8B—C9B—C10B—C11B	−3.1 (2)
C12A—C9A—C10A—C11A	−179.11 (13)	C12B—C9B—C10B—C11B	172.60 (13)
C8A—C9A—C10A—C23A	−177.84 (13)	C8B—C9B—C10B—C23B	175.86 (13)
C12A—C9A—C10A—C23A	0.6 (2)	C12B—C9B—C10B—C23B	−8.4 (2)
C7A—N1A—C11A—O1A	−176.51 (12)	C7B—N1B—C11B—O1B	−178.12 (12)
C7A—N1A—C11A—C10A	2.6 (2)	C7B—N1B—C11B—C10B	1.7 (2)
C18A—O1A—C11A—N1A	7.48 (19)	C18B—O1B—C11B—N1B	0.12 (19)
C18A—O1A—C11A—C10A	−171.71 (12)	C18B—O1B—C11B—C10B	−179.68 (12)
C9A—C10A—C11A—N1A	−4.7 (2)	C9B—C10B—C11B—N1B	1.0 (2)
C23A—C10A—C11A—N1A	175.50 (13)	C23B—C10B—C11B—N1B	−178.04 (13)
C9A—C10A—C11A—O1A	174.41 (12)	C9B—C10B—C11B—O1B	−179.24 (12)
C23A—C10A—C11A—O1A	−5.3 (2)	C23B—C10B—C11B—O1B	1.8 (2)
C8A—C9A—C12A—C17A	101.45 (16)	C8B—C9B—C12B—C13B	−79.57 (18)
C10A—C9A—C12A—C17A	−77.02 (18)	C10B—C9B—C12B—C13B	104.76 (16)
C8A—C9A—C12A—C13A	−73.84 (18)	C8B—C9B—C12B—C17B	93.84 (16)
C10A—C9A—C12A—C13A	107.69 (16)	C10B—C9B—C12B—C17B	−81.82 (17)
C20A—O2A—C13A—C14A	2.99 (19)	C20B—O2B—C13B—C12B	−178.53 (11)
C20A—O2A—C13A—C12A	−176.57 (11)	C20B—O2B—C13B—C14B	2.69 (18)
C17A—C12A—C13A—O2A	178.24 (12)	C17B—C12B—C13B—O2B	−178.96 (11)
C9A—C12A—C13A—O2A	−6.38 (19)	C9B—C12B—C13B—O2B	−5.51 (19)
C17A—C12A—C13A—C14A	−1.3 (2)	C17B—C12B—C13B—C14B	−0.2 (2)
C9A—C12A—C13A—C14A	174.04 (13)	C9B—C12B—C13B—C14B	173.29 (13)
O2A—C13A—C14A—C15A	178.92 (12)	O2B—C13B—C14B—C15B	176.43 (12)
C12A—C13A—C14A—C15A	−1.5 (2)	C12B—C13B—C14B—C15B	−2.3 (2)
C21A—O3A—C15A—C16A	4.8 (2)	C21B—O3B—C15B—C14B	−4.1 (2)
C21A—O3A—C15A—C14A	−176.65 (16)	C21B—O3B—C15B—C16B	176.73 (15)
C13A—C14A—C15A—O3A	−175.49 (13)	C13B—C14B—C15B—O3B	−176.30 (13)
C13A—C14A—C15A—C16A	3.1 (2)	C13B—C14B—C15B—C16B	2.8 (2)
O3A—C15A—C16A—C17A	176.75 (13)	O3B—C15B—C16B—C17B	178.31 (13)
C14A—C15A—C16A—C17A	−1.7 (2)	C14B—C15B—C16B—C17B	−0.9 (2)
C22A—O4A—C17A—C12A	175.92 (12)	C22B—O4B—C17B—C16B	1.3 (2)
C22A—O4A—C17A—C16A	−6.2 (2)	C22B—O4B—C17B—C12B	−176.93 (12)
C13A—C12A—C17A—O4A	−179.24 (12)	C15B—C16B—C17B—O4B	−179.75 (13)
C9A—C12A—C17A—O4A	5.36 (18)	C15B—C16B—C17B—C12B	−1.7 (2)
C13A—C12A—C17A—C16A	2.8 (2)	C13B—C12B—C17B—O4B	−179.59 (12)
C9A—C12A—C17A—C16A	−172.59 (13)	C9B—C12B—C17B—O4B	6.66 (18)
C15A—C16A—C17A—O4A	−179.09 (13)	C13B—C12B—C17B—C16B	2.2 (2)
C15A—C16A—C17A—C12A	−1.3 (2)	C9B—C12B—C17B—C16B	−171.56 (13)
C11A—O1A—C18A—C19A	173.84 (12)	C11B—O1B—C18B—C19B	−177.23 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C1A—H1AA···N1A	0.93	2.45	2.7872 (19)	101
C1A—H1AA···O4Bi	0.93	2.60	3.4813 (18)	159
C8A—H8AA···O2B	0.93	2.44	3.3391 (16)	162
C1B—H1BA···N1B	0.93	2.43	2.7751 (19)	102
C8B—H8BA···O2A	0.93	2.39	3.2889 (16)	162
C18A—H18B···O4Bi	0.97	2.57	3.3360 (18)	136
C20A—H20B···O2Aii	0.96	2.58	3.2869 (17)	131
C20B—H20E···O2Biii	0.96	2.55	3.2169 (17)	126
C21A—H21B···O3Biv	0.96	2.57	3.154 (2)	119
C22A—H22B···N2Biii	0.96	2.58	3.479 (2)	155
C18B—H18D···Cg1iv	0.97	2.93	3.7798 (16)	147
C20A—H20C···Cg3	0.96	2.60	3.5075 (15)	157
C20B—H20F···Cg2	0.96	2.51	3.3845 (15)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1A—H1AA⋯N1A	0.93	2.45	2.7872 (19)	101
C1A—H1AA⋯O4Bi	0.93	2.60	3.4813 (18)	159
C8A—H8AA⋯O2B	0.93	2.44	3.3391 (16)	162
C1B—H1BA⋯N1B	0.93	2.43	2.7751 (19)	102
C8B—H8BA⋯O2A	0.93	2.39	3.2889 (16)	162
C18A—H18B⋯O4Bi	0.97	2.57	3.3360 (18)	136
C20A—H20B⋯O2Aii	0.96	2.58	3.2869 (17)	131
C20B—H20E⋯O2Biii	0.96	2.55	3.2169 (17)	126
C21A—H21B⋯O3Biv	0.96	2.57	3.154 (2)	119
C22A—H22B⋯N2Biii	0.96	2.58	3.479 (2)	155
C18B—H18D⋯Cg1iv	0.97	2.93	3.7798 (16)	147
C20A—H20C⋯Cg3	0.96	2.60	3.5075 (15)	157
C20B—H20F⋯Cg2	0.96	2.51	3.3845 (15)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1, Cg2 and Cg3 are the centroids of the C7A–C11A/N1A, C12A–C17A and C12B–C17B rings, respectively.