Dibromido[1,1'-dibutyl-2,2'-(pentane-1,1-di-yl)di-1H-benzimidazole]-copper(II).

In the title compound, [CuBr(2)(C(27)H(36)N(4))], the Cu(II) ion exhibits a distorted tetra-hedral coordination geometry provided by two bromide ions and by chelation of two imine N-atom donors from a bis-(benzimidazole) ligand. Chelation results in a six-membered boat-shaped ring which links the benzimidazole groups. Each bis-(benzimidazole) fragment contains three n-butyl substituents, two of which have the expected trans conformation; the third exhibits the higher-energy cis conformation, an orientation consistent with several short intra-molecular C-H⋯Br inter-actions. Essentially planar (r.m.s. deviations of 0.0101 and 0.0183 Å) benzimidazole groups are oriented so as to give the bis-(benzimidazole) fragment a V-shaped appearance in profile with the cis and trans n-butyl groups directed to opposite sides of the planes. In the crystal, columns of mol-ecules along the b-axis direction form layers parallel to the (202) planes. Within a given column, the mol-ecules are linked by C-H⋯Br hydrogen bonds. The mol-ecules in adjacent columns are also linked by inter-molecular C-H⋯π interactions, forming a three-dimensional network.

Related literature

For the applications of bis­(imidazoles), bis­(benzimidazoles), and their complexes with metal ions, see: Stibrany et al. (2002 ▶, 2003 ▶, 2004 ▶); Knapp et al. (1990 ▶). For related structures see: Stibrany (2009 ▶); Stibrany et al. 2005 ▶); Stibrany & Potenza (2006 ▶, 2008 ▶); Hou et al. (2006 ▶).

Experimental

Crystal data

[CuBr2(C27H36N4)]

M = 639.96

Monoclinic,

a = 13.521 (2) Å

b = 14.604 (3) Å

c = 13.881 (2) Å

β = 96.636 (3)°

V = 2722.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 3.76 mm−1

T = 100 K

0.45 × 0.18 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.644, T max = 1.00

25644 measured reflections

5405 independent reflections

4692 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.066

S = 1.00

5405 reflections

310 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-32 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681002088X/lh5058sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002088X/lh5058Isup2.hkl

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

[CuBr2(C27H36N4)]	F(000) = 1300
Mr = 639.96	Dx = 1.561 Mg m−3
Monoclinic, P21/n	Melting point: 486 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 13.521 (2) Å	Cell parameters from 982 reflections
b = 14.604 (3) Å	θ = 2.2–25.9°
c = 13.881 (2) Å	µ = 3.76 mm−1
β = 96.636 (3)°	T = 100 K
V = 2722.6 (8) Å3	Blade, red
Z = 4	0.45 × 0.18 × 0.07 mm

Bruker SMART CCD area-detector diffractometer	5405 independent reflections
Radiation source: fine-focus sealed tube	4692 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 26.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −16→16
Tmin = 0.644, Tmax = 1.00	k = −18→18
25644 measured reflections	l = −17→16

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0324P)2 + 2.745P] where P = (Fo2 + 2Fc2)/3
5405 reflections	(Δ/σ)max = 0.001
310 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.38 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
Cu1	0.10186 (2)	0.119645 (19)	0.230340 (19)	0.01124 (8)
Br1	0.045118 (19)	−0.023221 (16)	0.167330 (18)	0.01896 (7)
Br2	−0.049244 (18)	0.184464 (17)	0.267178 (17)	0.01820 (7)
N11	0.34142 (15)	0.24098 (13)	0.12023 (14)	0.0130 (4)
N13	0.20969 (15)	0.16010 (13)	0.15332 (14)	0.0122 (4)
N21	0.30460 (14)	0.21513 (13)	0.45058 (14)	0.0131 (4)
N23	0.18474 (14)	0.15045 (13)	0.35070 (13)	0.0115 (4)
C1	0.27426 (17)	0.27602 (15)	0.27828 (16)	0.0116 (5)
H1	0.3394	0.3081	0.2948	0.014*
C2	0.18961 (18)	0.34819 (16)	0.26140 (17)	0.0146 (5)
H2A	0.2043	0.3897	0.2085	0.018*
H2B	0.1265	0.3162	0.2395	0.018*
C3	0.17497 (19)	0.40545 (17)	0.35029 (18)	0.0188 (5)
H3A	0.2319	0.4479	0.3640	0.023*
H3B	0.1739	0.3646	0.4071	0.023*
C4	0.0784 (2)	0.46057 (19)	0.3362 (2)	0.0280 (6)
H4A	0.0215	0.4175	0.3301	0.034*
H4B	0.0739	0.4983	0.3948	0.034*
C5	0.0688 (2)	0.52288 (19)	0.2482 (2)	0.0321 (7)
H5A	0.0632	0.4857	0.1890	0.048*
H5B	0.1279	0.5621	0.2503	0.048*
H5C	0.0093	0.5611	0.2484	0.048*
C11	0.31456 (18)	0.18592 (16)	0.03975 (17)	0.0141 (5)
C12	0.27675 (17)	0.22314 (16)	0.18544 (16)	0.0118 (5)
C13	0.23188 (18)	0.13538 (16)	0.06078 (17)	0.0135 (5)
C14	0.18405 (18)	0.07574 (17)	−0.00812 (17)	0.0159 (5)
H14	0.1276	0.0411	0.0049	0.019*
C15	0.22204 (19)	0.06923 (18)	−0.09575 (18)	0.0206 (5)
H15	0.1911	0.0291	−0.1440	0.025*
C16	0.3049 (2)	0.1202 (2)	−0.11563 (19)	0.0254 (6)
H16	0.3288	0.1137	−0.1770	0.030*
C17	0.3529 (2)	0.17963 (18)	−0.04871 (18)	0.0199 (5)
H17	0.4091	0.2144	−0.0622	0.024*
C18	0.42282 (19)	0.30825 (16)	0.12849 (19)	0.0175 (5)
H18A	0.4043	0.3605	0.1682	0.021*
H18B	0.4310	0.3319	0.0630	0.021*
C19	0.52200 (19)	0.26958 (18)	0.17390 (19)	0.0211 (5)
H19A	0.5114	0.2389	0.2355	0.025*
H19B	0.5685	0.3212	0.1900	0.025*
C1A	0.5710 (2)	0.20174 (19)	0.1109 (2)	0.0250 (6)
H1A1	0.5247	0.1503	0.0936	0.030*
H1A2	0.5842	0.2324	0.0501	0.030*
C1B	0.6683 (2)	0.1643 (2)	0.1619 (2)	0.0350 (7)
H1B1	0.6549	0.1296	0.2194	0.053*
H1B2	0.7134	0.2151	0.1815	0.053*
H1B3	0.6993	0.1239	0.1175	0.053*
C21	0.26253 (18)	0.14778 (15)	0.50387 (17)	0.0131 (5)
C22	0.25617 (17)	0.21300 (15)	0.35975 (16)	0.0112 (5)
C23	0.18673 (18)	0.10799 (16)	0.44063 (17)	0.0129 (5)
C24	0.12813 (18)	0.03726 (16)	0.47082 (17)	0.0152 (5)
H24	0.0759	0.0107	0.4282	0.018*
C25	0.14950 (19)	0.00760 (17)	0.56540 (18)	0.0187 (5)
H25	0.1114	−0.0407	0.5884	0.022*
C26	0.2264 (2)	0.04736 (17)	0.62821 (18)	0.0193 (5)
H26	0.2392	0.0248	0.6926	0.023*
C27	0.28417 (19)	0.11836 (17)	0.59950 (17)	0.0172 (5)
H27	0.3357	0.1455	0.6425	0.021*
C29	0.48784 (19)	0.24181 (18)	0.46606 (19)	0.0216 (6)
H29A	0.5389	0.2877	0.4896	0.026*
H29B	0.4872	0.2372	0.3948	0.026*
C28	0.38695 (18)	0.27632 (17)	0.48784 (18)	0.0167 (5)
H28A	0.3876	0.2827	0.5589	0.020*
H28B	0.3751	0.3377	0.4586	0.020*
C2A	0.5186 (2)	0.14970 (18)	0.5108 (2)	0.0226 (6)
H2A1	0.4689	0.1029	0.4865	0.027*
H2A2	0.5193	0.1536	0.5821	0.027*
C2B	0.6213 (2)	0.1199 (2)	0.4870 (2)	0.0291 (6)
H2B1	0.6709	0.1657	0.5114	0.044*
H2B2	0.6203	0.1141	0.4166	0.044*
H2B3	0.6384	0.0607	0.5177	0.044*

	U11	U22	U33	U12	U13	U23
Cu1	0.01029 (15)	0.01486 (14)	0.00862 (14)	−0.00107 (11)	0.00129 (11)	−0.00152 (11)
Br1	0.01931 (14)	0.01686 (13)	0.02065 (13)	−0.00290 (10)	0.00205 (10)	−0.00428 (10)
Br2	0.01408 (13)	0.02410 (14)	0.01700 (13)	0.00417 (10)	0.00434 (9)	−0.00078 (10)
N11	0.0141 (10)	0.0135 (10)	0.0115 (10)	−0.0003 (8)	0.0023 (8)	0.0012 (8)
N13	0.0134 (10)	0.0129 (9)	0.0106 (9)	0.0011 (8)	0.0025 (8)	−0.0001 (8)
N21	0.0134 (10)	0.0136 (10)	0.0121 (10)	−0.0023 (8)	0.0006 (8)	0.0010 (8)
N23	0.0133 (10)	0.0123 (9)	0.0088 (9)	0.0001 (8)	0.0007 (8)	0.0007 (7)
C1	0.0120 (11)	0.0123 (11)	0.0107 (11)	−0.0004 (9)	0.0019 (9)	0.0011 (9)
C2	0.0169 (13)	0.0129 (11)	0.0141 (12)	0.0003 (9)	0.0015 (9)	0.0011 (9)
C3	0.0214 (14)	0.0182 (12)	0.0172 (13)	0.0023 (10)	0.0038 (10)	−0.0035 (10)
C4	0.0233 (15)	0.0259 (14)	0.0359 (16)	0.0070 (12)	0.0078 (12)	−0.0091 (12)
C5	0.0291 (16)	0.0205 (14)	0.0444 (19)	0.0098 (12)	−0.0054 (14)	−0.0088 (13)
C11	0.0141 (12)	0.0166 (12)	0.0116 (11)	0.0024 (9)	0.0020 (9)	0.0021 (9)
C12	0.0108 (11)	0.0142 (11)	0.0104 (11)	0.0032 (9)	0.0011 (9)	0.0035 (9)
C13	0.0141 (12)	0.0156 (12)	0.0112 (11)	0.0057 (9)	0.0028 (9)	0.0011 (9)
C14	0.0155 (12)	0.0184 (12)	0.0136 (12)	0.0021 (10)	0.0005 (9)	−0.0002 (10)
C15	0.0188 (13)	0.0277 (14)	0.0148 (12)	−0.0010 (11)	−0.0005 (10)	−0.0048 (10)
C16	0.0232 (14)	0.0417 (16)	0.0121 (13)	0.0002 (12)	0.0063 (11)	−0.0020 (11)
C17	0.0174 (13)	0.0284 (14)	0.0151 (12)	−0.0025 (11)	0.0067 (10)	0.0003 (10)
C18	0.0197 (13)	0.0150 (12)	0.0192 (13)	−0.0050 (10)	0.0078 (10)	0.0023 (10)
C19	0.0161 (13)	0.0224 (13)	0.0247 (14)	−0.0059 (10)	0.0027 (11)	0.0011 (11)
C1A	0.0202 (14)	0.0263 (14)	0.0295 (15)	−0.0002 (11)	0.0073 (12)	0.0036 (12)
C1B	0.0213 (15)	0.0355 (17)	0.049 (2)	0.0031 (13)	0.0057 (14)	0.0073 (15)
C21	0.0140 (12)	0.0115 (11)	0.0142 (11)	−0.0002 (9)	0.0037 (9)	0.0002 (9)
C22	0.0114 (11)	0.0123 (11)	0.0103 (11)	0.0015 (9)	0.0025 (9)	−0.0009 (9)
C23	0.0128 (12)	0.0144 (11)	0.0117 (11)	0.0016 (9)	0.0019 (9)	−0.0013 (9)
C24	0.0150 (12)	0.0159 (12)	0.0147 (12)	−0.0028 (10)	0.0021 (9)	−0.0018 (9)
C25	0.0200 (13)	0.0190 (12)	0.0181 (13)	−0.0030 (10)	0.0068 (10)	0.0010 (10)
C26	0.0248 (14)	0.0213 (13)	0.0117 (12)	0.0016 (11)	0.0021 (10)	0.0012 (10)
C27	0.0211 (13)	0.0195 (12)	0.0104 (12)	−0.0013 (10)	−0.0004 (10)	−0.0002 (9)
C29	0.0164 (13)	0.0274 (14)	0.0201 (13)	−0.0068 (11)	−0.0017 (10)	0.0035 (11)
C28	0.0191 (13)	0.0158 (12)	0.0143 (12)	−0.0063 (10)	−0.0029 (10)	0.0010 (10)
C2A	0.0201 (14)	0.0242 (13)	0.0233 (14)	−0.0033 (11)	0.0017 (11)	−0.0019 (11)
C2B	0.0227 (15)	0.0338 (16)	0.0304 (16)	0.0012 (12)	0.0018 (12)	−0.0054 (13)

Cu1—N23	1.9536 (19)	C16—C17	1.377 (4)
Cu1—N13	1.994 (2)	C16—H16	0.9500
Cu1—Br1	2.3563 (5)	C17—H17	0.9500
Cu1—Br2	2.3608 (5)	C18—C19	1.523 (4)
N11—C12	1.354 (3)	C18—H18A	0.9900
N11—C11	1.390 (3)	C18—H18B	0.9900
N11—C18	1.470 (3)	C19—C1A	1.523 (4)
N13—C12	1.332 (3)	C19—H19A	0.9900
N13—C13	1.400 (3)	C19—H19B	0.9900
N21—C22	1.352 (3)	C1A—C1B	1.522 (4)
N21—C21	1.391 (3)	C1A—H1A1	0.9900
N21—C28	1.474 (3)	C1A—H1A2	0.9900
N23—C22	1.325 (3)	C1B—H1B1	0.9800
N23—C23	1.391 (3)	C1B—H1B2	0.9800
C1—C22	1.500 (3)	C1B—H1B3	0.9800
C1—C12	1.506 (3)	C21—C27	1.394 (3)
C1—C2	1.554 (3)	C21—C23	1.397 (3)
C1—H1	1.0000	C23—C24	1.395 (3)
C2—C3	1.522 (3)	C24—C25	1.381 (3)
C2—H2A	0.9900	C24—H24	0.9500
C2—H2B	0.9900	C25—C26	1.403 (4)
C3—C4	1.527 (4)	C25—H25	0.9500
C3—H3A	0.9900	C26—C27	1.384 (4)
C3—H3B	0.9900	C26—H26	0.9500
C4—C5	1.517 (4)	C27—H27	0.9500
C4—H4A	0.9900	C29—C28	1.517 (4)
C4—H4B	0.9900	C29—C2A	1.519 (4)
C5—H5A	0.9800	C29—H29A	0.9900
C5—H5B	0.9800	C29—H29B	0.9900
C5—H5C	0.9800	C28—H28A	0.9900
C11—C17	1.390 (3)	C28—H28B	0.9900
C11—C13	1.398 (3)	C2A—C2B	1.526 (4)
C13—C14	1.396 (3)	C2A—H2A1	0.9900
C14—C15	1.377 (3)	C2A—H2A2	0.9900
C14—H14	0.9500	C2B—H2B1	0.9800
C15—C16	1.400 (4)	C2B—H2B2	0.9800
C15—H15	0.9500	C2B—H2B3	0.9800
N23—Cu1—N13	90.44 (8)	N11—C18—C19	113.6 (2)
N23—Cu1—Br1	130.64 (6)	N11—C18—H18A	108.9
N13—Cu1—Br1	106.87 (6)	C19—C18—H18A	108.9
N23—Cu1—Br2	98.49 (6)	N11—C18—H18B	108.9
N13—Cu1—Br2	134.58 (6)	C19—C18—H18B	108.9
Br1—Cu1—Br2	100.523 (16)	H18A—C18—H18B	107.7
C12—N11—C11	107.27 (19)	C18—C19—C1A	115.1 (2)
C12—N11—C18	127.7 (2)	C18—C19—H19A	108.5
C11—N11—C18	125.0 (2)	C1A—C19—H19A	108.5
C12—N13—C13	105.99 (19)	C18—C19—H19B	108.5
C12—N13—Cu1	122.46 (16)	C1A—C19—H19B	108.5
C13—N13—Cu1	131.53 (16)	H19A—C19—H19B	107.5
C22—N21—C21	107.20 (19)	C1B—C1A—C19	112.2 (2)
C22—N21—C28	127.3 (2)	C1B—C1A—H1A1	109.2
C21—N21—C28	125.5 (2)	C19—C1A—H1A1	109.2
C22—N23—C23	106.50 (19)	C1B—C1A—H1A2	109.2
C22—N23—Cu1	125.43 (15)	C19—C1A—H1A2	109.2
C23—N23—Cu1	127.91 (16)	H1A1—C1A—H1A2	107.9
C22—C1—C12	110.63 (19)	C1A—C1B—H1B1	109.5
C22—C1—C2	110.39 (19)	C1A—C1B—H1B2	109.5
C12—C1—C2	107.92 (18)	H1B1—C1B—H1B2	109.5
C22—C1—H1	109.3	C1A—C1B—H1B3	109.5
C12—C1—H1	109.3	H1B1—C1B—H1B3	109.5
C2—C1—H1	109.3	H1B2—C1B—H1B3	109.5
C3—C2—C1	114.4 (2)	N21—C21—C27	132.1 (2)
C3—C2—H2A	108.7	N21—C21—C23	106.0 (2)
C1—C2—H2A	108.7	C27—C21—C23	121.9 (2)
C3—C2—H2B	108.7	N23—C22—N21	111.9 (2)
C1—C2—H2B	108.7	N23—C22—C1	122.2 (2)
H2A—C2—H2B	107.6	N21—C22—C1	125.8 (2)
C2—C3—C4	112.0 (2)	N23—C23—C24	130.3 (2)
C2—C3—H3A	109.2	N23—C23—C21	108.4 (2)
C4—C3—H3A	109.2	C24—C23—C21	121.3 (2)
C2—C3—H3B	109.2	C25—C24—C23	117.0 (2)
C4—C3—H3B	109.2	C25—C24—H24	121.5
H3A—C3—H3B	107.9	C23—C24—H24	121.5
C5—C4—C3	114.3 (2)	C24—C25—C26	121.3 (2)
C5—C4—H4A	108.7	C24—C25—H25	119.3
C3—C4—H4A	108.7	C26—C25—H25	119.3
C5—C4—H4B	108.7	C27—C26—C25	122.2 (2)
C3—C4—H4B	108.7	C27—C26—H26	118.9
H4A—C4—H4B	107.6	C25—C26—H26	118.9
C4—C5—H5A	109.5	C26—C27—C21	116.2 (2)
C4—C5—H5B	109.5	C26—C27—H27	121.9
H5A—C5—H5B	109.5	C21—C27—H27	121.9
C4—C5—H5C	109.5	C28—C29—C2A	115.0 (2)
H5A—C5—H5C	109.5	C28—C29—H29A	108.5
H5B—C5—H5C	109.5	C2A—C29—H29A	108.5
C17—C11—N11	131.2 (2)	C28—C29—H29B	108.5
C17—C11—C13	122.6 (2)	C2A—C29—H29B	108.5
N11—C11—C13	106.2 (2)	H29A—C29—H29B	107.5
N13—C12—N11	112.1 (2)	N21—C28—C29	112.9 (2)
N13—C12—C1	124.0 (2)	N21—C28—H28A	109.0
N11—C12—C1	123.6 (2)	C29—C28—H28A	109.0
C14—C13—C11	120.3 (2)	N21—C28—H28B	109.0
C14—C13—N13	131.2 (2)	C29—C28—H28B	109.0
C11—C13—N13	108.5 (2)	H28A—C28—H28B	107.8
C15—C14—C13	117.2 (2)	C29—C2A—C2B	112.2 (2)
C15—C14—H14	121.4	C29—C2A—H2A1	109.2
C13—C14—H14	121.4	C2B—C2A—H2A1	109.2
C14—C15—C16	121.8 (2)	C29—C2A—H2A2	109.2
C14—C15—H15	119.1	C2B—C2A—H2A2	109.2
C16—C15—H15	119.1	H2A1—C2A—H2A2	107.9
C17—C16—C15	121.9 (2)	C2A—C2B—H2B1	109.5
C17—C16—H16	119.1	C2A—C2B—H2B2	109.5
C15—C16—H16	119.1	H2B1—C2B—H2B2	109.5
C16—C17—C11	116.3 (2)	C2A—C2B—H2B3	109.5
C16—C17—H17	121.9	H2B1—C2B—H2B3	109.5
C11—C17—H17	121.9	H2B2—C2B—H2B3	109.5
N23—Cu1—N13—C12	−27.22 (18)	C14—C15—C16—C17	0.0 (4)
Br1—Cu1—N13—C12	−160.30 (16)	C15—C16—C17—C11	0.1 (4)
Br2—Cu1—N13—C12	75.19 (19)	N11—C11—C17—C16	−176.7 (3)
N23—Cu1—N13—C13	154.6 (2)	C13—C11—C17—C16	−0.1 (4)
Br1—Cu1—N13—C13	21.6 (2)	C12—N11—C18—C19	91.0 (3)
Br2—Cu1—N13—C13	−102.9 (2)	C11—N11—C18—C19	−91.9 (3)
N13—Cu1—N23—C22	26.70 (19)	N11—C18—C19—C1A	70.4 (3)
Br1—Cu1—N23—C22	139.59 (16)	C18—C19—C1A—C1B	−178.6 (2)
Br2—Cu1—N23—C22	−108.60 (18)	C22—N21—C21—C27	178.3 (3)
N13—Cu1—N23—C23	−147.9 (2)	C28—N21—C21—C27	−1.4 (4)
Br1—Cu1—N23—C23	−35.1 (2)	C22—N21—C21—C23	−1.1 (3)
Br2—Cu1—N23—C23	76.75 (19)	C28—N21—C21—C23	179.1 (2)
C22—C1—C2—C3	56.9 (3)	C23—N23—C22—N21	−0.7 (3)
C12—C1—C2—C3	178.0 (2)	Cu1—N23—C22—N21	−176.26 (15)
C1—C2—C3—C4	−168.1 (2)	C23—N23—C22—C1	−177.4 (2)
C2—C3—C4—C5	−56.2 (3)	Cu1—N23—C22—C1	7.0 (3)
C12—N11—C11—C17	177.0 (3)	C21—N21—C22—N23	1.1 (3)
C18—N11—C11—C17	−0.6 (4)	C28—N21—C22—N23	−179.1 (2)
C12—N11—C11—C13	−0.1 (3)	C21—N21—C22—C1	177.7 (2)
C18—N11—C11—C13	−177.6 (2)	C28—N21—C22—C1	−2.5 (4)
C13—N13—C12—N11	−0.2 (3)	C12—C1—C22—N23	−47.6 (3)
Cu1—N13—C12—N11	−178.77 (15)	C2—C1—C22—N23	71.8 (3)
C13—N13—C12—C1	173.4 (2)	C12—C1—C22—N21	136.1 (2)
Cu1—N13—C12—C1	−5.2 (3)	C2—C1—C22—N21	−104.5 (3)
C11—N11—C12—N13	0.2 (3)	C22—N23—C23—C24	−179.5 (2)
C18—N11—C12—N13	177.7 (2)	Cu1—N23—C23—C24	−4.1 (4)
C11—N11—C12—C1	−173.5 (2)	C22—N23—C23—C21	−0.1 (3)
C18—N11—C12—C1	4.0 (4)	Cu1—N23—C23—C21	175.39 (16)
C22—C1—C12—N13	46.7 (3)	N21—C21—C23—N23	0.7 (3)
C2—C1—C12—N13	−74.2 (3)	C27—C21—C23—N23	−178.8 (2)
C22—C1—C12—N11	−140.4 (2)	N21—C21—C23—C24	−179.7 (2)
C2—C1—C12—N11	98.7 (3)	C27—C21—C23—C24	0.7 (4)
C17—C11—C13—C14	−0.1 (4)	N23—C23—C24—C25	178.5 (2)
N11—C11—C13—C14	177.3 (2)	C21—C23—C24—C25	−1.0 (4)
C17—C11—C13—N13	−177.5 (2)	C23—C24—C25—C26	0.3 (4)
N11—C11—C13—N13	−0.1 (3)	C24—C25—C26—C27	0.5 (4)
C12—N13—C13—C14	−176.8 (2)	C25—C26—C27—C21	−0.7 (4)
Cu1—N13—C13—C14	1.6 (4)	N21—C21—C27—C26	−179.3 (2)
C12—N13—C13—C11	0.2 (3)	C23—C21—C27—C26	0.1 (4)
Cu1—N13—C13—C11	178.54 (16)	C22—N21—C28—C29	−83.8 (3)
C11—C13—C14—C15	0.2 (3)	C21—N21—C28—C29	95.9 (3)
N13—C13—C14—C15	176.9 (2)	C2A—C29—C28—N21	−61.6 (3)
C13—C14—C15—C16	−0.2 (4)	C28—C29—C2A—C2B	−179.3 (2)

Cg1 is the centroid of the N11/C11/C13/N13/C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Br1	0.95	2.79	3.551 (3)	138
C17—H17···Br2i	0.95	2.90	3.606 (3)	132
C18—H18A···Br1ii	0.99	2.86	3.741 (3)	148
C5—H5B···Cg1iii	0.98	2.87	3.631 (3)	135
C2B—H2B1···Cg1iv	0.98	2.82	3.777 (3)	165

Cu1—N23	1.9536 (19)
Cu1—N13	1.994 (2)
Cu1—Br1	2.3563 (5)
Cu1—Br2	2.3608 (5)

N23—Cu1—N13	90.44 (8)
N23—Cu1—Br1	130.64 (6)
N13—Cu1—Br1	106.87 (6)
N23—Cu1—Br2	98.49 (6)
N13—Cu1—Br2	134.58 (6)
Br1—Cu1—Br2	100.523 (16)
C22—C1—C12	110.63 (19)

Table 2

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N11/C11/C13/N13/C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯Br1	0.95	2.79	3.551 (3)	138
C17—H17⋯Br2i	0.95	2.90	3.606 (3)	132
C18—H18A⋯Br1ii	0.99	2.86	3.741 (3)	148
C5—H5B⋯Cg1ii	0.98	2.87	3.631 (3)	135
C2B—H2B1⋯Cg1iii	0.98	2.82	3.777 (3)	165

Symmetry codes: (i) ; (ii) ; (iii) .