[Bis(quinolin-2-ylcarbon-yl)amido-κ(3) N,N',N'']bromido-(N,N-di-methyl-formamide-κO)copper(II).

In the mononuclear title complex, [CuBr(C20H12N3O2)(C3H7NO)], synthesized from the quinoline-derived reduced Schiff base 4-(quinolin-2-ylmeth-yl)amino-phenol, the coordination geometry around Cu(2+) is distorted square-pyramidal, comprising a bromide anion at the apex [Cu-Br = 2.4671 (5) Å]. The base of the pyramid is built up from one di-methyl-formamide O-atom donor [Cu-O = 2.078 (2) Å] and three N-atom donors from the monoanionic, tridentate bis-(quinolin-2-ylcarbon-yl)di-imide ligand [Cu-Ndi-imide = 1.941 (3) Å, and Cu-Nquinol-yl = 2.060 (3) and 2.049 (3) Å]. An intra-molecular C-H⋯O occurs. In the crystal, weak methyl and aromatic C-H⋯Br and formyl C-H⋯Ocarbon-yl hydrogen-bonding inter-actions generate an overall layered structure lying parallel to (001).

Related literature

For applications of the title complex and related structures, see: Castro et al. (1990 ▶, 1991 ▶, 1999 ▶); Vangdal et al. (2002 ▶); Sahu et al. (2010 ▶); Carlucci et al. (2011 ▶); Calatayud et al. (2000 ▶); Lebon et al. (1998 ▶).

Experimental

Crystal data

[CuBr(C20H12N3O2)(C3H7NO)]

M = 542.87

Monoclinic,

a = 9.2137 (6) Å

b = 23.5220 (16) Å

c = 10.4842 (7) Å

β = 110.284 (1)°

V = 2131.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.93 mm−1

T = 100 K

0.26 × 0.20 × 0.14 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.592, T max = 0.681

13799 measured reflections

3753 independent reflections

3223 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.081

S = 1.06

3753 reflections

301 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.81 e Å−3

Δρmin = −0.45 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenberg & Putz, 2006 ▶); software used to prepare material for publication: DIAMOND.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814010058/zs2296sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010058/zs2296Isup2.hkl

CCDC reference: 1000734

Additional supporting information: crystallographic information; 3D view; checkCIF report

[CuBr(C20H12N3O2)(C3H7NO)]	F(000) = 1092
Mr = 542.87	Dx = 1.692 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7192 reflections
a = 9.2137 (6) Å	θ = 2.2–28.3°
b = 23.5220 (16) Å	µ = 2.93 mm−1
c = 10.4842 (7) Å	T = 100 K
β = 110.284 (1)°	Needle, red
V = 2131.3 (2) Å3	0.26 × 0.20 × 0.14 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3753 independent reflections
Radiation source: fine-focus sealed tube	3223 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω and φ scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
Tmin = 0.592, Tmax = 0.681	k = −27→27
13799 measured reflections	l = −12→10

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0432P)2 + 2.2471P] where P = (Fo2 + 2Fc2)/3
3753 reflections	(Δ/σ)max = 0.001
301 parameters	Δρmax = 0.81 e Å−3
0 restraints	Δρmin = −0.45 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
C1	1.2311 (4)	0.17727 (13)	0.9003 (3)	0.0186 (7)
C2	1.2627 (4)	0.11829 (14)	0.9138 (3)	0.0225 (8)
H2	1.1818	0.0922	0.8872	0.027*
C3	1.4112 (4)	0.09975 (15)	0.9655 (3)	0.0276 (8)
H3	1.4309	0.0609	0.9747	0.033*
C4	1.5355 (4)	0.13798 (16)	1.0051 (4)	0.0305 (9)
H4	1.6365	0.1244	1.0397	0.037*
C5	1.5086 (4)	0.19471 (16)	0.9931 (4)	0.0294 (9)
H5	1.5916	0.2199	1.0191	0.035*
C6	1.3571 (4)	0.21600 (14)	0.9420 (3)	0.0245 (8)
C7	1.3227 (5)	0.27458 (15)	0.9297 (4)	0.0298 (9)
H7	1.4024	0.3011	0.9549	0.036*
C8	1.1742 (4)	0.29206 (14)	0.8811 (4)	0.0277 (8)
H8	1.1511	0.3307	0.8747	0.033*
C9	1.0551 (4)	0.25196 (13)	0.8405 (3)	0.0219 (8)
C10	0.8890 (4)	0.27133 (14)	0.7873 (3)	0.0238 (8)
N4	0.7906 (3)	0.22593 (11)	0.7571 (3)	0.0210 (6)
C12	0.6353 (4)	0.23086 (14)	0.7065 (3)	0.0249 (8)
C13	0.5577 (4)	0.17340 (14)	0.6804 (3)	0.0207 (7)
C14	0.3975 (4)	0.17069 (15)	0.6286 (3)	0.0255 (8)
H14	0.3388	0.2038	0.6070	0.031*
C15	0.3275 (4)	0.11898 (16)	0.6097 (3)	0.0292 (8)
H15	0.2202	0.1164	0.5748	0.035*
C16	0.4180 (4)	0.06968 (15)	0.6433 (3)	0.0235 (8)
C17	0.3511 (4)	0.01469 (16)	0.6265 (4)	0.0307 (9)
H17	0.2441	0.0106	0.5903	0.037*
C18	0.4423 (4)	−0.03185 (15)	0.6630 (4)	0.0304 (9)
H18	0.3975	−0.0678	0.6510	0.036*
C19	0.6035 (4)	−0.02662 (14)	0.7185 (3)	0.0269 (8)
H19	0.6643	−0.0590	0.7454	0.032*
C20	0.6726 (4)	0.02559 (14)	0.7337 (3)	0.0219 (7)
H20	0.7799	0.0285	0.7688	0.026*
C21	0.5808 (4)	0.07501 (14)	0.6959 (3)	0.0195 (7)
C22	0.9923 (4)	0.10622 (13)	1.0635 (3)	0.0191 (7)
H22	1.0592	0.1372	1.0867	0.023*
C23	1.0494 (6)	0.09139 (18)	1.3042 (4)	0.0348 (10)
C24	0.8692 (5)	0.02789 (15)	1.1333 (4)	0.0341 (9)
H24A	0.8694	0.0116	1.2173	0.051*
H24B	0.9036	0.0000	1.0833	0.051*
H24C	0.7663	0.0399	1.0806	0.051*
N1	1.0803 (3)	0.19603 (11)	0.8492 (3)	0.0183 (6)
N2	0.6487 (3)	0.12808 (11)	0.7128 (3)	0.0180 (6)
N3	0.9720 (3)	0.07624 (11)	1.1617 (3)	0.0219 (6)
O1	0.9264 (3)	0.09523 (9)	0.9413 (2)	0.0223 (5)
O2	0.8575 (3)	0.32184 (9)	0.7751 (3)	0.0337 (6)
O3	0.5551 (3)	0.27363 (10)	0.6817 (3)	0.0399 (7)
Cu1	0.87800 (5)	0.150012 (15)	0.77633 (4)	0.01711 (12)
Br1	0.93628 (4)	0.090477 (13)	0.60641 (3)	0.01868 (11)
H23A	0.972 (5)	0.1009 (16)	1.346 (4)	0.033 (11)*
H23B	1.114 (5)	0.0610 (18)	1.354 (4)	0.038 (11)*
H23C	1.111 (4)	0.1234 (17)	1.315 (4)	0.030 (11)*

	U11	U22	U33	U12	U13	U23
C1	0.0256 (18)	0.0192 (17)	0.0137 (16)	−0.0035 (14)	0.0102 (14)	−0.0026 (13)
C2	0.032 (2)	0.0153 (17)	0.0189 (17)	−0.0025 (14)	0.0067 (15)	0.0008 (13)
C3	0.033 (2)	0.0251 (19)	0.0238 (18)	0.0015 (16)	0.0085 (16)	0.0017 (15)
C4	0.028 (2)	0.034 (2)	0.0267 (19)	−0.0001 (17)	0.0058 (16)	0.0017 (16)
C5	0.030 (2)	0.034 (2)	0.0247 (19)	−0.0120 (17)	0.0100 (16)	−0.0072 (16)
C6	0.036 (2)	0.0228 (18)	0.0163 (17)	−0.0076 (16)	0.0110 (16)	−0.0064 (14)
C7	0.040 (2)	0.0210 (19)	0.030 (2)	−0.0163 (17)	0.0143 (18)	−0.0087 (15)
C8	0.045 (2)	0.0115 (16)	0.031 (2)	−0.0079 (16)	0.0188 (18)	−0.0034 (14)
C9	0.038 (2)	0.0120 (16)	0.0193 (17)	−0.0020 (14)	0.0138 (16)	−0.0019 (13)
C10	0.042 (2)	0.0134 (17)	0.0223 (18)	0.0008 (15)	0.0191 (17)	−0.0008 (13)
N4	0.0318 (17)	0.0102 (13)	0.0229 (15)	0.0016 (12)	0.0120 (13)	0.0002 (11)
C12	0.033 (2)	0.0202 (18)	0.0254 (19)	0.0062 (16)	0.0154 (16)	0.0062 (14)
C13	0.0279 (19)	0.0181 (17)	0.0183 (16)	0.0049 (15)	0.0107 (15)	0.0050 (13)
C14	0.0264 (19)	0.0274 (19)	0.0229 (18)	0.0069 (16)	0.0090 (15)	0.0060 (15)
C15	0.0232 (19)	0.041 (2)	0.0225 (18)	−0.0011 (17)	0.0068 (16)	0.0034 (16)
C16	0.0286 (19)	0.0279 (19)	0.0141 (16)	−0.0057 (15)	0.0073 (15)	−0.0014 (14)
C17	0.029 (2)	0.037 (2)	0.0237 (18)	−0.0135 (17)	0.0067 (16)	−0.0029 (16)
C18	0.040 (2)	0.0223 (19)	0.0288 (19)	−0.0165 (17)	0.0123 (18)	−0.0041 (15)
C19	0.040 (2)	0.0159 (17)	0.0259 (18)	−0.0040 (15)	0.0120 (17)	−0.0017 (14)
C20	0.0268 (18)	0.0182 (17)	0.0219 (17)	−0.0022 (14)	0.0100 (15)	−0.0020 (13)
C21	0.0280 (19)	0.0188 (17)	0.0133 (16)	−0.0031 (14)	0.0093 (14)	−0.0027 (13)
C22	0.0299 (19)	0.0083 (15)	0.0213 (18)	0.0001 (14)	0.0115 (15)	−0.0014 (13)
C23	0.061 (3)	0.028 (2)	0.0172 (18)	0.000 (2)	0.015 (2)	−0.0017 (16)
C24	0.039 (2)	0.026 (2)	0.036 (2)	−0.0036 (17)	0.0112 (18)	0.0131 (17)
N1	0.0292 (16)	0.0115 (14)	0.0165 (13)	−0.0043 (11)	0.0107 (12)	−0.0022 (10)
N2	0.0246 (15)	0.0150 (14)	0.0163 (14)	−0.0011 (11)	0.0095 (12)	0.0005 (11)
N3	0.0347 (17)	0.0133 (14)	0.0193 (14)	−0.0003 (12)	0.0114 (13)	0.0018 (11)
O1	0.0359 (14)	0.0137 (11)	0.0151 (12)	−0.0038 (10)	0.0061 (11)	0.0021 (9)
O2	0.0499 (17)	0.0094 (13)	0.0490 (17)	0.0040 (11)	0.0262 (14)	0.0010 (11)
O3	0.0388 (16)	0.0192 (14)	0.0627 (19)	0.0107 (12)	0.0188 (14)	0.0121 (13)
Cu1	0.0243 (2)	0.0083 (2)	0.0190 (2)	−0.00018 (15)	0.00791 (17)	0.00038 (15)
Br1	0.02579 (19)	0.01385 (17)	0.01721 (17)	0.00011 (13)	0.00847 (14)	−0.00126 (12)

Br1—Cu1	2.4671 (5)	C13—C14	1.386 (5)
Cu1—O1	2.078 (2)	C14—C15	1.359 (5)
Cu1—N1	2.060 (3)	C15—C16	1.400 (5)
Cu1—N2	2.049 (3)	C16—C17	1.417 (5)
Cu1—N4	1.941 (3)	C16—C21	1.413 (5)
O1—C22	1.240 (4)	C17—C18	1.352 (5)
O2—C10	1.219 (4)	C18—C19	1.400 (5)
O3—C12	1.222 (4)	C19—C20	1.367 (5)
N1—C1	1.377 (5)	C20—C21	1.411 (5)
N1—C9	1.334 (4)	C2—H2	0.9300
N2—C13	1.326 (4)	C3—H3	0.9300
N2—C21	1.380 (4)	C4—H4	0.9300
N3—C22	1.314 (4)	C5—H5	0.9300
N3—C23	1.459 (5)	C7—H7	0.9300
N3—C24	1.444 (5)	C8—H8	0.9300
N4—C10	1.365 (4)	C14—H14	0.9300
N4—C12	1.348 (5)	C15—H15	0.9300
C1—C2	1.415 (5)	C17—H17	0.9300
C1—C6	1.420 (5)	C18—H18	0.9300
C2—C3	1.357 (5)	C19—H19	0.9300
C3—C4	1.401 (5)	C20—H20	0.9300
C4—C5	1.355 (5)	C22—H22	0.9300
C5—C6	1.403 (5)	C23—H23A	0.98 (5)
C6—C7	1.410 (5)	C23—H23B	0.96 (4)
C7—C8	1.348 (6)	C23—H23C	0.93 (4)
C8—C9	1.397 (5)	C24—H24A	0.9600
C9—C10	1.506 (5)	C24—H24B	0.9600
C12—C13	1.509 (5)	C24—H24C	0.9600
Br1—Cu1—O1	102.21 (6)	C15—C16—C17	122.0 (3)
Br1—Cu1—N1	99.83 (8)	C15—C16—C21	118.9 (3)
Br1—Cu1—N2	94.61 (8)	C17—C16—C21	119.1 (3)
Br1—Cu1—N4	129.33 (9)	C16—C17—C18	120.2 (4)
O1—Cu1—N1	96.41 (11)	C17—C18—C19	120.8 (3)
O1—Cu1—N2	90.80 (11)	C18—C19—C20	120.8 (3)
O1—Cu1—N4	128.23 (11)	C19—C20—C21	119.9 (3)
N1—Cu1—N2	162.09 (11)	N2—C21—C16	120.2 (3)
N1—Cu1—N4	81.05 (12)	N2—C21—C20	120.6 (3)
N2—Cu1—N4	81.60 (11)	C16—C21—C20	119.2 (3)
Cu1—O1—C22	128.2 (2)	O1—C22—N3	123.1 (3)
Cu1—N1—C1	129.6 (2)	C1—C2—H2	120.00
Cu1—N1—C9	112.3 (2)	C3—C2—H2	120.00
C1—N1—C9	118.1 (3)	C2—C3—H3	119.00
Cu1—N2—C13	111.7 (2)	C4—C3—H3	119.00
Cu1—N2—C21	129.8 (2)	C3—C4—H4	120.00
C13—N2—C21	118.4 (3)	C5—C4—H4	120.00
C22—N3—C23	121.3 (3)	C4—C5—H5	120.00
C22—N3—C24	121.5 (3)	C6—C5—H5	120.00
C23—N3—C24	117.2 (3)	C6—C7—H7	120.00
Cu1—N4—C10	118.5 (2)	C8—C7—H7	120.00
Cu1—N4—C12	117.8 (2)	C7—C8—H8	120.00
C10—N4—C12	123.6 (3)	C9—C8—H8	120.00
N1—C1—C2	119.9 (3)	C13—C14—H14	120.00
N1—C1—C6	121.4 (3)	C15—C14—H14	120.00
C2—C1—C6	118.7 (3)	C14—C15—H15	120.00
C1—C2—C3	119.9 (3)	C16—C15—H15	120.00
C2—C3—C4	121.3 (3)	C16—C17—H17	120.00
C3—C4—C5	120.0 (4)	C18—C17—H17	120.00
C4—C5—C6	120.9 (4)	C17—C18—H18	120.00
C1—C6—C5	119.2 (3)	C19—C18—H18	120.00
C1—C6—C7	117.7 (3)	C18—C19—H19	120.00
C5—C6—C7	123.1 (4)	C20—C19—H19	120.00
C6—C7—C8	120.0 (4)	C19—C20—H20	120.00
C7—C8—C9	119.8 (3)	C21—C20—H20	120.00
N1—C9—C8	123.1 (3)	O1—C22—H22	118.00
N1—C9—C10	117.0 (3)	N3—C22—H22	118.00
C8—C9—C10	119.9 (3)	N3—C23—H23A	110 (2)
O2—C10—N4	128.6 (3)	N3—C23—H23B	111 (2)
O2—C10—C9	120.5 (3)	N3—C23—H23C	113 (2)
N4—C10—C9	110.9 (3)	H23A—C23—H23B	110 (3)
O3—C12—N4	129.5 (3)	H23A—C23—H23C	106 (3)
O3—C12—C13	119.0 (3)	H23B—C23—H23C	108 (4)
N4—C12—C13	111.5 (3)	N3—C24—H24A	109.00
N2—C13—C12	117.1 (3)	N3—C24—H24B	110.00
N2—C13—C14	123.8 (3)	N3—C24—H24C	109.00
C12—C13—C14	119.0 (3)	H24A—C24—H24B	109.00
C13—C14—C15	119.0 (3)	H24A—C24—H24C	109.00
C14—C15—C16	119.6 (3)	H24B—C24—H24C	110.00
C6—C1—C2—C3	−0.1 (5)	C12—C13—C14—C15	−177.7 (3)
N1—C1—C2—C3	−179.3 (3)	N2—C13—C14—C15	0.4 (5)
C2—C1—C6—C5	1.0 (5)	C12—C13—N2—C21	177.2 (3)
C2—C1—C6—C7	−179.1 (3)	C12—C13—N2—Cu1	−5.0 (4)
N1—C1—C6—C5	−179.8 (3)	C14—C13—N2—C21	−0.9 (5)
N1—C1—C6—C7	0.1 (5)	C14—C13—N2—Cu1	177.0 (3)
C2—C1—N1—C9	178.7 (3)	C13—C14—C15—C16	0.1 (5)
C2—C1—N1—Cu1	−2.9 (5)	C14—C15—C16—C17	179.6 (3)
C6—C1—N1—C9	−0.4 (5)	C14—C15—C16—C21	−0.1 (5)
C6—C1—N1—Cu1	177.9 (2)	C15—C16—C17—C18	−178.5 (3)
C1—C2—C3—C4	−0.6 (5)	C21—C16—C17—C18	1.2 (5)
C2—C3—C4—C5	0.4 (6)	C15—C16—C21—C20	178.0 (3)
C3—C4—C5—C6	0.5 (6)	C15—C16—C21—N2	−0.4 (5)
C4—C5—C6—C1	−1.3 (5)	C17—C16—C21—C20	−1.6 (5)
C4—C5—C6—C7	178.9 (4)	C17—C16—C21—N2	179.9 (3)
C1—C6—C7—C8	0.8 (5)	C16—C17—C18—C19	0.5 (6)
C5—C6—C7—C8	−179.3 (4)	C17—C18—C19—C20	−1.8 (6)
C6—C7—C8—C9	−1.3 (6)	C18—C19—C20—C21	1.4 (5)
C7—C8—C9—C10	179.5 (3)	C19—C20—C21—C16	0.4 (5)
C7—C8—C9—N1	1.0 (6)	C19—C20—C21—N2	178.8 (3)
C8—C9—C10—N4	−178.3 (3)	C16—C21—N2—C13	0.9 (5)
C8—C9—C10—O2	2.4 (5)	C16—C21—N2—Cu1	−176.5 (2)
N1—C9—C10—N4	0.4 (4)	C20—C21—N2—C13	−177.5 (3)
N1—C9—C10—O2	−179.0 (3)	C20—C21—N2—Cu1	5.1 (5)
C8—C9—N1—C1	−0.1 (5)	O1—C22—N3—C23	−178.7 (3)
C8—C9—N1—Cu1	−178.7 (3)	O1—C22—N3—C24	−0.4 (5)
C10—C9—N1—C1	−178.6 (3)	N3—C22—O1—Cu1	155.7 (2)
C10—C9—N1—Cu1	2.7 (4)	C1—N1—Cu1—N4	178.0 (3)
C9—C10—N4—C12	−179.4 (3)	C1—N1—Cu1—N2	163.4 (3)
C9—C10—N4—Cu1	−3.6 (4)	C1—N1—Cu1—O1	50.2 (3)
O2—C10—N4—C12	−0.0 (6)	C1—N1—Cu1—Br1	−53.4 (3)
O2—C10—N4—Cu1	175.7 (3)	C9—N1—Cu1—N4	−3.6 (2)
C10—N4—C12—C13	178.7 (3)	C9—N1—Cu1—N2	−18.2 (5)
C10—N4—C12—O3	−1.9 (6)	C9—N1—Cu1—O1	−131.4 (2)
Cu1—N4—C12—C13	3.0 (4)	C9—N1—Cu1—Br1	125.0 (2)
Cu1—N4—C12—O3	−177.6 (3)	C13—N2—Cu1—N4	5.1 (2)
C10—N4—Cu1—N1	4.1 (2)	C13—N2—Cu1—N1	19.6 (5)
C10—N4—Cu1—N2	179.6 (3)	C13—N2—Cu1—O1	133.6 (2)
C10—N4—Cu1—O1	95.2 (3)	C13—N2—Cu1—Br1	−124.1 (2)
C10—N4—Cu1—Br1	−91.4 (2)	C21—N2—Cu1—N4	−177.4 (3)
C12—N4—Cu1—N1	−180.0 (3)	C21—N2—Cu1—N1	−162.8 (3)
C12—N4—Cu1—N2	−4.5 (2)	C21—N2—Cu1—O1	−48.8 (3)
C12—N4—Cu1—O1	−88.8 (3)	C21—N2—Cu1—Br1	53.5 (3)
C12—N4—Cu1—Br1	84.6 (3)	C22—O1—Cu1—N4	−45.9 (3)
N4—C12—C13—C14	179.8 (3)	C22—O1—Cu1—N1	37.8 (3)
N4—C12—C13—N2	1.6 (4)	C22—O1—Cu1—N2	−125.8 (3)
O3—C12—C13—C14	0.3 (5)	C22—O1—Cu1—Br1	139.3 (3)
O3—C12—C13—N2	−177.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23A···Br1i	0.98 (5)	2.87 (4)	3.663 (5)	138 (3)
C15—H15···Br1ii	0.93	2.82	3.655 (4)	151
C20—H20···O1	0.93	2.42	3.059 (4)	126
C22—H22···O3iii	0.93	2.33	3.060 (4)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23A⋯Br1i	0.98 (5)	2.87 (4)	3.663 (5)	138 (3)
C15—H15⋯Br1ii	0.93	2.82	3.655 (4)	151
C20—H20⋯O1	0.93	2.42	3.059 (4)	126
C22—H22⋯O3iii	0.93	2.33	3.060 (4)	135

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