(Dimethyl­formamide-κO){4,4′,6,6′-tetra­bromo-2,2′-[o-phenyl­enebis(nitrilo­methyl­idyne)]diphenolato-κ4O,N,N′,O′}copper(II) dimethyl­formamide solvate

Wu, Y.; Xie, B.; Zou, L.-K.; Wu, W.-P.; Lu, L.

doi:10.1107/S160053680902162X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m758

doi:10.1107/S160053680902162X

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(Dimethylformamide-κO){4,4′,6,6′-tetrabromo-2,2′-[o-phenylenebis(nitrilomethylidyne)]diphenolato-κ⁴O,N,N′,O′}copper(II) dimethylformamide solvate

Yu Wu,^a ^* Bin Xie,^a Li-Ke Zou,^a Wei-Ping Wu ^a and Lu Lu ^a

^aCollege of Chemistry and Pharmaceutical Engineering, Sichuan University of Science and Engineering, Zigong, Sichuan 643000, People's Republic of China
^*Correspondence e-mail: solicitor.wu@126.com

(Received 30 May 2009; accepted 7 June 2009; online 10 June 2009)

In the title compound, [Cu(C₂₀H₁₀Br₄N₂O₂)(C₃H₇NO)]·C₃H₇NO, the Cu^II ion is coordinated by two N atoms and two O atoms from a tetradentate Schiff base ligand and the O atom of one dimethylformamide ligand in an almost square-pyramidal geometry. The uncoordinated dimethylformamide solvent molecule is disordered over two sets of positions with occupancies of 0.741 (4) and 0.259 (4). The crystal packing is stabilized by C—H⋯O interactions.

Related literature

For the preparation of 3,5-dibromosalicylaldehyde, see: Elzbieta et al. (1964 ). For a related structure, see: Bei et al. (2003 ).

Experimental

Crystal data

[Cu(C₂₀H₁₀Br₄N₂O₂)(C₃H₇NO)]·C₃H₇NO
M_r = 839.67
Triclinic, $[P \overline 1]$
a = 7.3742 (10) Å
b = 11.9542 (19) Å
c = 17.212 (2) Å
α = 94.207 (9)°
β = 100.310 (6)°
γ = 104.117 (5)°
V = 1436.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 6.36 mm⁻¹
T = 93 K
0.25 × 0.25 × 0.25 mm

Data collection

Rigaku SPIDER diffractometer
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 2004 ) T_min = 0.299, T_max = 0.299 (expected range = 0.204–0.204)
11906 measured reflections
6330 independent reflections
5305 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.063
S = 1.02
6330 reflections
392 parameters
8 restraints
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.910 (2)
Cu1—O2	1.9174 (19)
Cu1—N1	1.954 (2)
Cu1—N2	1.958 (2)
Cu1—O3	2.501 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3ⁱ	0.95	2.47	3.319 (4)	148
C7—H7⋯O3ⁱ	0.95	2.37	3.243 (4)	153
C14—H14⋯O4ⁱⁱ	0.95	2.33	3.226 (14)	156
C22—H22A⋯O1	0.98	2.54	3.378 (4)	143
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z+2.

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902162X/ci2819sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902162X/ci2819Isup2.hkl

checkCIF report

Comment top

The crystal structure and some properties of 1,2-N,N'-disalicylidenephenylaminato-nickel(II) was previously reported by Bei et al. (2003). We report here the synthesis and crystal structure of the title complex, [Cu(C₁₄H₈N₂O₃Br₂)(C₃H₇NO)](C₃H₇NO).

The contents of the asymmetric unit are shown in Fig.1. The Cu^II ion is coordinated by two N atoms and two O atoms from one 4,4',6,6'-tetrabromo-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenolate dianion and one O atom of N,N-dimethylformamide ligand in a square-pyramidal geometry (Table 1). The crystal packing is stabilized by C—H···O interactions (Table 2).

Related literature top

For the preparation of 3,5-dibromosalicylaldehyde, see: Elzbieta et al. (1964). For a related structure, see: Bei et al. (2003).

Experimental top

The title complex was synthesized in two stages. In the first stage, 3,5- dibromosalicylaldehyde was prepared according to Elzbieta et al. (1964). Two mole equivalents of 3,5-dibromosalicylaldehyde in ethanol (50 ml) was slowly added to 1,2-phenylenediamine (6 g) in ethanol (100 ml) with continuous stirring. The Schiff base molecule, viz. 4,4',6,6'-tetrabromo-2,2'-[1,2-phenylenebis(nitrilomethylidyne)] diphenol, precipitated immediately. In the second stage, the ligand (1 mmol), Cu(OAc)₂ (1 mmol) and DMF (25 ml) were refluxed for 1 h. The hot solution was filtered and allowed to stand at room temperature undisturbed for about three weeks, resulting in dark green crystals.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the title complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for the sake of clarity. Both disorder components of the uncoordinated solvent molecule are shown.

(Dimethylformamide-κO){4,4',6,6'-tetrabromo-2,2'-[o- phenylenebis(nitrilomethylidyne)]diphenolato- κ⁴O,N,N',O'}copper(II) dimethylformamide solvate top

Crystal data top

[Cu(C₂₀H₁₀Br₄N₂O₂)(C₃H₇NO)]·C₃H₇NO	Z = 2
M_r = 839.67	F(000) = 818
Triclinic, P1	D_x = 1.941 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3742 (10) Å	Cell parameters from 4531 reflections
b = 11.9542 (19) Å	θ = 3.1–27.5°
c = 17.212 (2) Å	µ = 6.36 mm⁻¹
α = 94.207 (9)°	T = 93 K
β = 100.310 (6)°	Block, dark green
γ = 104.117 (5)°	0.25 × 0.25 × 0.25 mm
V = 1436.8 (3) Å³

Data collection top

Rigaku SPIDER diffractometer	6330 independent reflections
Radiation source: Rotating Anode	5305 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 2004)	h = −8→9
T_min = 0.299, T_max = 0.299	k = −15→15
11906 measured reflections	l = −22→22

Refinement top

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0247P)²] where P = (F_o² + 2F_c²)/3
6330 reflections	(Δ/σ)_max = 0.002
392 parameters	Δρ_max = 0.75 e Å⁻³
8 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Cu(C₂₀H₁₀Br₄N₂O₂)(C₃H₇NO)]·C₃H₇NO	γ = 104.117 (5)°
M_r = 839.67	V = 1436.8 (3) Å³
Triclinic, P1	Z = 2
a = 7.3742 (10) Å	Mo Kα radiation
b = 11.9542 (19) Å	µ = 6.36 mm⁻¹
c = 17.212 (2) Å	T = 93 K
α = 94.207 (9)°	0.25 × 0.25 × 0.25 mm
β = 100.310 (6)°

Data collection top

Rigaku SPIDER diffractometer	6330 independent reflections
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 2004)	5305 reflections with I > 2σ(I)
T_min = 0.299, T_max = 0.299	R_int = 0.027
11906 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	8 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 1.02	Δρ_max = 0.75 e Å⁻³
6330 reflections	Δρ_min = −0.52 e Å⁻³
392 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.39299 (5)	0.60816 (3)	0.67052 (2)	0.01305 (9)
Br1	0.12215 (5)	0.88993 (3)	0.535887 (19)	0.01998 (8)
Br2	−0.00681 (5)	0.60574 (3)	0.244696 (18)	0.02312 (9)
Br3	0.74637 (5)	0.75127 (3)	1.105720 (18)	0.02390 (9)
Br4	0.49378 (5)	0.96915 (3)	0.842406 (19)	0.02212 (9)
O1	0.2620 (3)	0.69347 (17)	0.60103 (11)	0.0141 (5)
O2	0.4409 (3)	0.73265 (18)	0.75456 (11)	0.0152 (5)
N1	0.3449 (3)	0.4761 (2)	0.58884 (14)	0.0124 (5)
N2	0.4835 (4)	0.5038 (2)	0.74155 (14)	0.0142 (6)
C1	0.2062 (4)	0.6699 (3)	0.52455 (17)	0.0129 (6)
C2	0.1319 (4)	0.7497 (3)	0.48000 (17)	0.0137 (6)
C3	0.0698 (4)	0.7320 (3)	0.39909 (17)	0.0150 (7)
H3	0.0224	0.7885	0.3718	0.018*
C4	0.0777 (4)	0.6295 (3)	0.35772 (17)	0.0161 (7)
C5	0.1450 (4)	0.5472 (3)	0.39550 (17)	0.0157 (7)
H5	0.1484	0.4777	0.3660	0.019*
C6	0.2099 (4)	0.5664 (3)	0.47917 (17)	0.0125 (6)
C7	0.2743 (4)	0.4742 (3)	0.51432 (18)	0.0142 (6)
H7	0.2642	0.4061	0.4799	0.017*
C8	0.3973 (4)	0.3788 (3)	0.61884 (18)	0.0134 (6)
C9	0.3827 (4)	0.2740 (3)	0.57325 (19)	0.0172 (7)
H9	0.3361	0.2643	0.5174	0.021*
C10	0.4360 (4)	0.1849 (3)	0.60964 (19)	0.0191 (7)
H10	0.4272	0.1139	0.5788	0.023*
C11	0.5026 (5)	0.1987 (3)	0.69131 (19)	0.0217 (7)
H11	0.5367	0.1361	0.7159	0.026*
C12	0.5201 (4)	0.3013 (3)	0.73727 (19)	0.0184 (7)
H12	0.5667	0.3097	0.7931	0.022*
C13	0.4690 (4)	0.3924 (3)	0.70124 (18)	0.0139 (6)
C14	0.5440 (4)	0.5275 (3)	0.81769 (17)	0.0149 (7)
H14	0.5803	0.4682	0.8457	0.018*
C15	0.5606 (4)	0.6358 (3)	0.86300 (17)	0.0147 (7)
C16	0.6296 (4)	0.6425 (3)	0.94604 (17)	0.0168 (7)
H16	0.6600	0.5771	0.9680	0.020*
C17	0.6526 (4)	0.7431 (3)	0.99485 (17)	0.0172 (7)
C18	0.6111 (4)	0.8407 (3)	0.96363 (18)	0.0174 (7)
H18	0.6280	0.9104	0.9976	0.021*
C19	0.5458 (4)	0.8344 (3)	0.88351 (18)	0.0156 (7)
C20	0.5124 (4)	0.7327 (3)	0.82895 (17)	0.0142 (7)
O3	0.7162 (3)	0.69177 (19)	0.64181 (13)	0.0218 (5)
N3	0.8292 (4)	0.8852 (2)	0.68559 (16)	0.0251 (7)
C21	0.8417 (5)	0.7771 (3)	0.6803 (2)	0.0272 (8)
H21	0.9556	0.7628	0.7081	0.033*
C22	0.6627 (5)	0.9150 (3)	0.6398 (2)	0.0278 (8)
H22A	0.5753	0.8447	0.6082	0.033*
H22B	0.7052	0.9719	0.6043	0.033*
H22C	0.5967	0.9483	0.6765	0.033*
C23	0.9791 (6)	0.9809 (3)	0.7305 (3)	0.0478 (12)
H23A	1.0806	0.9512	0.7597	0.057*
H23B	0.9273	1.0233	0.7682	0.057*
H23C	1.0315	1.0333	0.6941	0.057*
O4	1.225 (3)	0.6119 (8)	1.0649 (3)	0.0317 (16)	0.741 (4)
C24	1.1892 (7)	0.7023 (4)	1.0473 (2)	0.0281 (12)	0.741 (4)
H24	1.2090	0.7632	1.0891	0.034*	0.741 (4)
N4	1.1242 (16)	0.7216 (4)	0.9731 (2)	0.0216 (12)	0.741 (4)
C25	1.0952 (8)	0.8347 (4)	0.9571 (4)	0.0382 (14)	0.741 (4)
H25A	1.1095	0.8828	1.0075	0.046*	0.741 (4)
H25B	0.9665	0.8243	0.9254	0.046*	0.741 (4)
H25C	1.1900	0.8729	0.9276	0.046*	0.741 (4)
C26	1.0890 (7)	0.6327 (4)	0.9057 (3)	0.0340 (13)	0.741 (4)
H26A	1.1286	0.5649	0.9240	0.041*	0.741 (4)
H26B	1.1622	0.6637	0.8663	0.041*	0.741 (4)
H26C	0.9525	0.6095	0.8815	0.041*	0.741 (4)
O4'	1.229 (8)	0.603 (3)	1.0485 (10)	0.0317 (16)	0.26
C24'	1.1591 (17)	0.6115 (9)	0.9800 (7)	0.018 (3)	0.259 (4)
H24'	1.1272	0.5434	0.9429	0.022*	0.259 (4)
N4'	1.123 (5)	0.7071 (13)	0.9520 (7)	0.0216 (12)	0.26
C25'	1.0462 (17)	0.7099 (12)	0.8680 (6)	0.022 (3)	0.259 (4)
H25D	1.1422	0.7618	0.8453	0.026*	0.259 (4)
H25E	0.9312	0.7383	0.8630	0.026*	0.259 (4)
H25F	1.0138	0.6314	0.8395	0.026*	0.259 (4)
C26'	1.1704 (18)	0.8156 (10)	1.0052 (7)	0.019 (3)	0.259 (4)
H26D	1.0541	0.8407	1.0070	0.023*	0.259 (4)
H26E	1.2613	0.8756	0.9854	0.023*	0.259 (4)
H26F	1.2280	0.8034	1.0587	0.023*	0.259 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0175 (2)	0.01176 (19)	0.01046 (18)	0.00541 (16)	0.00143 (15)	0.00295 (15)
Br1	0.02559 (19)	0.01350 (16)	0.02113 (17)	0.00819 (14)	0.00104 (14)	0.00254 (13)
Br2	0.02115 (18)	0.0359 (2)	0.01140 (16)	0.00857 (15)	−0.00079 (13)	0.00359 (14)
Br3	0.02659 (19)	0.0333 (2)	0.01011 (16)	0.00644 (15)	0.00017 (14)	0.00550 (14)
Br4	0.0337 (2)	0.01807 (17)	0.01618 (16)	0.01086 (15)	0.00296 (14)	0.00318 (13)
O1	0.0191 (12)	0.0135 (11)	0.0094 (10)	0.0063 (9)	−0.0006 (9)	0.0018 (9)
O2	0.0226 (12)	0.0148 (11)	0.0090 (10)	0.0081 (10)	0.0009 (9)	0.0018 (9)
N1	0.0110 (13)	0.0112 (13)	0.0143 (13)	0.0025 (10)	0.0010 (11)	0.0016 (11)
N2	0.0157 (14)	0.0127 (13)	0.0164 (13)	0.0049 (11)	0.0060 (11)	0.0050 (11)
C1	0.0115 (15)	0.0142 (16)	0.0120 (15)	0.0013 (12)	0.0015 (12)	0.0045 (13)
C2	0.0134 (16)	0.0121 (15)	0.0160 (16)	0.0029 (12)	0.0038 (13)	0.0035 (13)
C3	0.0103 (15)	0.0182 (17)	0.0167 (16)	0.0031 (13)	0.0013 (13)	0.0080 (13)
C4	0.0119 (16)	0.0222 (18)	0.0114 (15)	0.0017 (13)	−0.0014 (13)	0.0032 (14)
C5	0.0166 (17)	0.0175 (17)	0.0127 (15)	0.0043 (13)	0.0039 (13)	−0.0017 (13)
C6	0.0146 (16)	0.0131 (16)	0.0118 (15)	0.0057 (13)	0.0043 (13)	0.0027 (13)
C7	0.0143 (16)	0.0127 (16)	0.0160 (16)	0.0014 (13)	0.0070 (13)	0.0017 (13)
C8	0.0093 (15)	0.0114 (15)	0.0209 (16)	0.0021 (12)	0.0058 (13)	0.0060 (13)
C9	0.0149 (16)	0.0156 (16)	0.0202 (17)	0.0039 (13)	0.0013 (14)	0.0027 (14)
C10	0.0188 (17)	0.0125 (16)	0.0267 (18)	0.0047 (14)	0.0064 (15)	0.0015 (14)
C11	0.0241 (19)	0.0177 (17)	0.0294 (19)	0.0095 (14)	0.0117 (15)	0.0127 (15)
C12	0.0197 (17)	0.0226 (18)	0.0181 (17)	0.0098 (14)	0.0088 (14)	0.0086 (14)
C13	0.0145 (16)	0.0113 (15)	0.0179 (16)	0.0041 (12)	0.0064 (13)	0.0031 (13)
C14	0.0146 (16)	0.0183 (17)	0.0144 (15)	0.0055 (13)	0.0049 (13)	0.0094 (13)
C15	0.0122 (16)	0.0202 (17)	0.0120 (15)	0.0049 (13)	0.0017 (13)	0.0029 (13)
C16	0.0147 (16)	0.0237 (18)	0.0150 (16)	0.0085 (14)	0.0028 (13)	0.0101 (14)
C17	0.0158 (17)	0.0257 (18)	0.0085 (15)	0.0039 (14)	0.0001 (13)	0.0027 (14)
C18	0.0152 (17)	0.0217 (18)	0.0151 (16)	0.0047 (14)	0.0036 (13)	0.0003 (14)
C19	0.0168 (17)	0.0161 (16)	0.0159 (16)	0.0066 (13)	0.0042 (13)	0.0049 (13)
C20	0.0113 (16)	0.0193 (17)	0.0127 (15)	0.0041 (13)	0.0034 (12)	0.0037 (13)
O3	0.0247 (13)	0.0146 (12)	0.0243 (13)	0.0014 (10)	0.0073 (11)	−0.0015 (10)
N3	0.0296 (17)	0.0163 (15)	0.0258 (16)	0.0010 (13)	0.0043 (13)	−0.0002 (13)
C21	0.030 (2)	0.029 (2)	0.0271 (19)	0.0131 (17)	0.0084 (17)	0.0096 (17)
C22	0.036 (2)	0.0224 (19)	0.0259 (19)	0.0092 (17)	0.0055 (17)	0.0013 (16)
C23	0.047 (3)	0.023 (2)	0.057 (3)	−0.0038 (19)	−0.012 (2)	−0.001 (2)
O4	0.0336 (19)	0.031 (2)	0.029 (3)	0.0112 (18)	−0.003 (4)	0.011 (2)
C24	0.021 (3)	0.032 (3)	0.027 (3)	0.004 (2)	−0.002 (2)	0.006 (2)
N4	0.0193 (16)	0.021 (2)	0.024 (3)	0.005 (2)	0.001 (4)	0.007 (2)
C25	0.030 (3)	0.035 (3)	0.056 (4)	0.012 (3)	0.014 (3)	0.023 (3)
C26	0.024 (3)	0.049 (4)	0.032 (3)	0.010 (3)	0.008 (2)	0.012 (3)
O4'	0.0336 (19)	0.031 (2)	0.029 (3)	0.0112 (18)	−0.003 (4)	0.011 (2)
C24'	0.013 (6)	0.013 (6)	0.028 (7)	−0.004 (5)	0.007 (6)	0.011 (6)
N4'	0.0193 (16)	0.021 (2)	0.024 (3)	0.005 (2)	0.001 (4)	0.007 (2)
C25'	0.014 (7)	0.037 (8)	0.014 (6)	0.006 (6)	−0.003 (5)	0.016 (6)
C26'	0.013 (7)	0.021 (8)	0.024 (7)	0.005 (6)	0.004 (6)	−0.002 (6)

Geometric parameters (Å, º) top

Cu1—O1	1.910 (2)	C16—C17	1.372 (4)
Cu1—O2	1.9174 (19)	C16—H16	0.95
Cu1—N1	1.954 (2)	C17—C18	1.397 (4)
Cu1—N2	1.958 (2)	C18—C19	1.367 (4)
Cu1—O3	2.501 (2)	C18—H18	0.95
Br1—C2	1.894 (3)	C19—C20	1.423 (4)
Br2—C4	1.911 (3)	O3—C21	1.247 (4)
Br3—C17	1.897 (3)	N3—C21	1.316 (4)
Br4—C19	1.901 (3)	N3—C23	1.441 (4)
O1—C1	1.295 (3)	N3—C22	1.471 (4)
O2—C20	1.294 (3)	C21—H21	0.95
N1—C7	1.291 (4)	C22—H22A	0.98
N1—C8	1.416 (4)	C22—H22B	0.98
N2—C14	1.293 (4)	C22—H22C	0.98
N2—C13	1.426 (4)	C23—H23A	0.98
C1—C2	1.418 (4)	C23—H23B	0.98
C1—C6	1.423 (4)	C23—H23C	0.98
C2—C3	1.369 (4)	O4—C24	1.218 (3)
C3—C4	1.390 (4)	C24—N4	1.340 (3)
C3—H3	0.95	C24—H24	0.95
C4—C5	1.361 (4)	N4—C26	1.456 (3)
C5—C6	1.416 (4)	N4—C25	1.457 (3)
C5—H5	0.95	C25—H25A	0.98
C6—C7	1.434 (4)	C25—H25B	0.98
C7—H7	0.95	C25—H25C	0.98
C8—C9	1.399 (4)	C26—H26A	0.98
C8—C13	1.405 (4)	C26—H26B	0.98
C9—C10	1.377 (4)	C26—H26C	0.98
C9—H9	0.95	O4'—C24'	1.220 (3)
C10—C11	1.387 (4)	C24'—N4'	1.340 (3)
C10—H10	0.95	C24'—H24'	0.95
C11—C12	1.375 (4)	N4'—C25'	1.460 (3)
C11—H11	0.95	N4'—C26'	1.460 (3)
C12—C13	1.389 (4)	C25'—H25D	0.98
C12—H12	0.95	C25'—H25E	0.98
C14—C15	1.428 (4)	C25'—H25F	0.98
C14—H14	0.95	C26'—H26D	0.98
C15—C16	1.418 (4)	C26'—H26E	0.98
C15—C20	1.427 (4)	C26'—H26F	0.98

O1—Cu1—O2	89.11 (8)	C16—C15—C14	115.6 (3)
O1—Cu1—N1	93.40 (9)	C20—C15—C14	123.6 (3)
O2—Cu1—N1	177.19 (10)	C17—C16—C15	120.3 (3)
O1—Cu1—N2	170.18 (10)	C17—C16—H16	119.9
O2—Cu1—N2	93.64 (9)	C15—C16—H16	119.9
N1—Cu1—N2	83.67 (10)	C16—C17—C18	120.7 (3)
O1—Cu1—O3	96.00 (9)	C16—C17—Br3	119.8 (2)
O2—Cu1—O3	89.70 (8)	C18—C17—Br3	119.4 (2)
N1—Cu1—O3	91.29 (9)	C19—C18—C17	119.0 (3)
N2—Cu1—O3	93.44 (9)	C19—C18—H18	120.5
C1—O1—Cu1	126.73 (19)	C17—C18—H18	120.5
C20—O2—Cu1	126.9 (2)	C18—C19—C20	124.0 (3)
C7—N1—C8	121.5 (3)	C18—C19—Br4	118.1 (2)
C7—N1—Cu1	125.3 (2)	C20—C19—Br4	117.9 (2)
C8—N1—Cu1	113.22 (19)	O2—C20—C19	119.9 (3)
C14—N2—C13	121.4 (3)	O2—C20—C15	124.9 (3)
C14—N2—Cu1	125.7 (2)	C19—C20—C15	115.2 (3)
C13—N2—Cu1	112.92 (19)	C21—O3—Cu1	126.8 (2)
O1—C1—C2	119.9 (3)	C21—N3—C23	123.2 (3)
O1—C1—C6	125.0 (3)	C21—N3—C22	120.3 (3)
C2—C1—C6	115.1 (3)	C23—N3—C22	116.3 (3)
C3—C2—C1	123.8 (3)	O3—C21—N3	125.4 (3)
C3—C2—Br1	118.3 (2)	O3—C21—H21	117.3
C1—C2—Br1	117.8 (2)	N3—C21—H21	117.3
C2—C3—C4	118.6 (3)	N3—C22—H22A	109.5
C2—C3—H3	120.7	N3—C22—H22B	109.5
C4—C3—H3	120.7	H22A—C22—H22B	109.5
C5—C4—C3	121.8 (3)	N3—C22—H22C	109.5
C5—C4—Br2	119.8 (2)	H22A—C22—H22C	109.5
C3—C4—Br2	118.5 (2)	H22B—C22—H22C	109.5
C4—C5—C6	119.3 (3)	N3—C23—H23A	109.5
C4—C5—H5	120.3	N3—C23—H23B	109.5
C6—C5—H5	120.3	H23A—C23—H23B	109.5
C5—C6—C1	121.4 (3)	N3—C23—H23C	109.5
C5—C6—C7	115.7 (3)	H23A—C23—H23C	109.5
C1—C6—C7	123.0 (3)	H23B—C23—H23C	109.5
N1—C7—C6	125.4 (3)	O4—C24—N4	124.5 (4)
N1—C7—H7	117.3	O4—C24—H24	117.8
C6—C7—H7	117.3	N4—C24—H24	117.8
C9—C8—C13	119.4 (3)	C24—N4—C26	121.2 (4)
C9—C8—N1	125.2 (3)	C24—N4—C25	120.7 (4)
C13—C8—N1	115.3 (3)	C26—N4—C25	118.0 (4)
C10—C9—C8	119.8 (3)	O4'—C24'—N4'	126.4 (14)
C10—C9—H9	120.1	O4'—C24'—H24'	116.8
C8—C9—H9	120.1	N4'—C24'—H24'	116.8
C9—C10—C11	120.1 (3)	C24'—N4'—C25'	122.5 (11)
C9—C10—H10	119.9	C24'—N4'—C26'	119.9 (11)
C11—C10—H10	119.9	C25'—N4'—C26'	117.5 (10)
C12—C11—C10	121.2 (3)	N4'—C25'—H25D	109.5
C12—C11—H11	119.4	N4'—C25'—H25E	109.5
C10—C11—H11	119.4	H25D—C25'—H25E	109.5
C11—C12—C13	119.3 (3)	N4'—C25'—H25F	109.5
C11—C12—H12	120.3	H25D—C25'—H25F	109.5
C13—C12—H12	120.3	H25E—C25'—H25F	109.5
C12—C13—C8	120.1 (3)	N4'—C26'—H26D	109.5
C12—C13—N2	125.0 (3)	N4'—C26'—H26E	109.5
C8—C13—N2	114.8 (3)	H26D—C26'—H26E	109.5
N2—C14—C15	125.1 (3)	N4'—C26'—H26F	109.5
N2—C14—H14	117.4	H26D—C26'—H26F	109.5
C15—C14—H14	117.4	H26E—C26'—H26F	109.5
C16—C15—C20	120.8 (3)

O2—Cu1—O1—C1	169.2 (2)	C8—C9—C10—C11	0.5 (5)
N1—Cu1—O1—C1	−12.0 (2)	C9—C10—C11—C12	−1.2 (5)
O3—Cu1—O1—C1	79.6 (2)	C10—C11—C12—C13	0.4 (5)
O1—Cu1—O2—C20	171.6 (2)	C11—C12—C13—C8	1.0 (5)
N2—Cu1—O2—C20	1.1 (3)	C11—C12—C13—N2	−178.7 (3)
O3—Cu1—O2—C20	−92.4 (2)	C9—C8—C13—C12	−1.6 (5)
O1—Cu1—N1—C7	9.3 (3)	N1—C8—C13—C12	178.3 (3)
N2—Cu1—N1—C7	179.9 (3)	C9—C8—C13—N2	178.1 (3)
O3—Cu1—N1—C7	−86.8 (3)	N1—C8—C13—N2	−1.9 (4)
O1—Cu1—N1—C8	−171.3 (2)	C14—N2—C13—C12	−1.5 (5)
N2—Cu1—N1—C8	−0.7 (2)	Cu1—N2—C13—C12	−179.0 (3)
O3—Cu1—N1—C8	92.6 (2)	C14—N2—C13—C8	178.7 (3)
O2—Cu1—N2—C14	1.5 (3)	Cu1—N2—C13—C8	1.3 (3)
N1—Cu1—N2—C14	−177.6 (3)	C13—N2—C14—C15	−179.1 (3)
O3—Cu1—N2—C14	91.5 (3)	Cu1—N2—C14—C15	−2.0 (4)
O2—Cu1—N2—C13	178.8 (2)	N2—C14—C15—C16	179.7 (3)
N1—Cu1—N2—C13	−0.3 (2)	N2—C14—C15—C20	−0.4 (5)
O3—Cu1—N2—C13	−91.2 (2)	C20—C15—C16—C17	−0.6 (5)
Cu1—O1—C1—C2	−172.1 (2)	C14—C15—C16—C17	179.3 (3)
Cu1—O1—C1—C6	8.9 (4)	C15—C16—C17—C18	−0.9 (5)
O1—C1—C2—C3	179.9 (3)	C15—C16—C17—Br3	−179.6 (2)
C6—C1—C2—C3	−1.0 (5)	C16—C17—C18—C19	0.4 (5)
O1—C1—C2—Br1	1.0 (4)	Br3—C17—C18—C19	179.2 (2)
C6—C1—C2—Br1	−179.9 (2)	C17—C18—C19—C20	1.5 (5)
C1—C2—C3—C4	0.7 (5)	C17—C18—C19—Br4	−179.2 (2)
Br1—C2—C3—C4	179.6 (2)	Cu1—O2—C20—C19	177.6 (2)
C2—C3—C4—C5	0.0 (5)	Cu1—O2—C20—C15	−3.4 (4)
C2—C3—C4—Br2	−179.4 (2)	C18—C19—C20—O2	176.3 (3)
C3—C4—C5—C6	−0.3 (5)	Br4—C19—C20—O2	−3.0 (4)
Br2—C4—C5—C6	179.1 (2)	C18—C19—C20—C15	−2.8 (5)
C4—C5—C6—C1	0.0 (5)	Br4—C19—C20—C15	177.9 (2)
C4—C5—C6—C7	178.6 (3)	C16—C15—C20—O2	−176.8 (3)
O1—C1—C6—C5	179.7 (3)	C14—C15—C20—O2	3.3 (5)
C2—C1—C6—C5	0.6 (4)	C16—C15—C20—C19	2.3 (4)
O1—C1—C6—C7	1.1 (5)	C14—C15—C20—C19	−177.6 (3)
C2—C1—C6—C7	−177.9 (3)	O1—Cu1—O3—C21	94.1 (3)
C8—N1—C7—C6	177.3 (3)	O2—Cu1—O3—C21	5.0 (3)
Cu1—N1—C7—C6	−3.4 (4)	N1—Cu1—O3—C21	−172.4 (3)
C5—C6—C7—N1	177.4 (3)	N2—Cu1—O3—C21	−88.6 (3)
C1—C6—C7—N1	−4.0 (5)	Cu1—O3—C21—N3	−66.7 (4)
C7—N1—C8—C9	1.1 (5)	C23—N3—C21—O3	−179.6 (4)
Cu1—N1—C8—C9	−178.4 (2)	C22—N3—C21—O3	−4.2 (5)
C7—N1—C8—C13	−178.9 (3)	O4—C24—N4—C26	0.4 (17)
Cu1—N1—C8—C13	1.6 (3)	O4—C24—N4—C25	−176.8 (12)
C13—C8—C9—C10	0.9 (5)	O4'—C24'—N4'—C25'	177 (4)
N1—C8—C9—C10	−179.1 (3)	O4'—C24'—N4'—C26'	1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.95	2.47	3.319 (4)	148
C7—H7···O3ⁱ	0.95	2.37	3.243 (4)	153
C14—H14···O4ⁱⁱ	0.95	2.33	3.226 (14)	156
C22—H22A···O1	0.98	2.54	3.378 (4)	143

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[Cu(C₂₀H₁₀Br₄N₂O₂)(C₃H₇NO)]·C₃H₇NO
M_r	839.67
Crystal system, space group	Triclinic, P1
Temperature (K)	93
a, b, c (Å)	7.3742 (10), 11.9542 (19), 17.212 (2)
α, β, γ (°)	94.207 (9), 100.310 (6), 104.117 (5)
V (Å³)	1436.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	6.36
Crystal size (mm)	0.25 × 0.25 × 0.25

Data collection
Diffractometer	Rigaku SPIDER diffractometer
Absorption correction	Multi-scan (RAPID-AUTO; Rigaku, 2004)
T_min, T_max	0.299, 0.299
No. of measured, independent and observed [I > 2σ(I)] reflections	11906, 6330, 5305
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.063, 1.02
No. of reflections	6330
No. of parameters	392
No. of restraints	8
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.52

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Selected bond lengths (Å) top

Cu1—O1	1.910 (2)	Cu1—N2	1.958 (2)
Cu1—O2	1.9174 (19)	Cu1—O3	2.501 (2)
Cu1—N1	1.954 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.95	2.47	3.319 (4)	148
C7—H7···O3ⁱ	0.95	2.37	3.243 (4)	153
C14—H14···O4ⁱⁱ	0.95	2.33	3.226 (14)	156
C22—H22A···O1	0.98	2.54	3.378 (4)	143

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+2.

Acknowledgements

The authors acknowledge financial assistance from Sichuan University of Science and Engineering (grant No. 2007 ZR005), the Education Committee of Sichuan Province of China (grant Nos. 2006 A110 and 07ZA161) and the Science and Technology Office of Zigong City, China (grant No. 08X01).

References

Bei, F.-L., Ma, W.-X. & Wang, J. (2003). Chin. J. Inorg. Chem. 19, 609–612. Google Scholar
Elzbieta, C., Zygmunt, E. & Romuald, K. (1964). Diss. Pharm. 15, 369–378. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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