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Acta Cryst. (2009). E65, m758    [ doi:10.1107/S160053680902162X ]

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

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

Abstract top

In the title compound, [Cu(C20H10Br4N2O2)(C3H7NO)]·C3H7NO, the CuII 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.

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 CuII 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.

Refinement top

The uncoordinated N,N-dimethylformamide solvent molecule is disordered over two positions with occupancies of 0.741 (4) and 0.259 (4). The N—C(sp3), N—C(sp2) and C—O distances in both disorder components were restrained to 1.460 (3), 1.340 (3) and 1.220 (3) Å, respectively. H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 or 0.98 Å and Uiso(H) = 1.2Ueq(C).

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
[Figure 1] 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)]·C3H7NOZ = 2
Mr = 839.67F(000) = 818
Triclinic, P1Dx = 1.941 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3742 (10) ÅCell parameters from 4531 reflections
b = 11.9542 (19) Åθ = 3.1–27.5°
c = 17.212 (2) ŵ = 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 Anode5305 reflections with I > 2σ(I)
graphiteRint = 0.027
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(RAPID-AUTO; Rigaku, 2004)		h = −8→9
Tmin = 0.299, Tmax = 0.299k = −15→15
11906 measured reflectionsl = −22→22
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0247P)2]
where P = (Fo2 + 2Fc2)/3
6330 reflections(Δ/σ)max = 0.002
392 parametersΔρmax = 0.75 e Å−3
8 restraintsΔρmin = −0.52 e Å−3
Crystal data top
[Cu(C20H10Br4N2O2)(C3H7NO)]·C3H7NOγ = 104.117 (5)°
Mr = 839.67V = 1436.8 (3) Å3
Triclinic, P1Z = 2
a = 7.3742 (10) ÅMo Kα radiation
b = 11.9542 (19) ŵ = 6.36 mm−1
c = 17.212 (2) ÅT = 93 K
α = 94.207 (9)°0.25 × 0.25 × 0.25 mm
β = 100.310 (6)°
Data collection top
Rigaku SPIDER
diffractometer		5305 reflections with I > 2σ(I)
Absorption correction: multi-scan
(RAPID-AUTO; Rigaku, 2004)		Rint = 0.027
Tmin = 0.299, Tmax = 0.299θmax = 27.5°
11906 measured reflectionsStandard reflections: 0
6330 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.063Δρmax = 0.75 e Å−3
S = 1.02Δρmin = −0.52 e Å−3
6330 reflectionsAbsolute structure: ?
392 parametersFlack parameter: ?
8 restraintsRogers parameter: ?
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
xyzUiso*/UeqOcc. (<1)
Cu10.39299 (5)0.60816 (3)0.67052 (2)0.01305 (9)
Br10.12215 (5)0.88993 (3)0.535887 (19)0.01998 (8)
Br2−0.00681 (5)0.60574 (3)0.244696 (18)0.02312 (9)
Br30.74637 (5)0.75127 (3)1.105720 (18)0.02390 (9)
Br40.49378 (5)0.96915 (3)0.842406 (19)0.02212 (9)
O10.2620 (3)0.69347 (17)0.60103 (11)0.0141 (5)
O20.4409 (3)0.73265 (18)0.75456 (11)0.0152 (5)
N10.3449 (3)0.4761 (2)0.58884 (14)0.0124 (5)
N20.4835 (4)0.5038 (2)0.74155 (14)0.0142 (6)
C10.2062 (4)0.6699 (3)0.52455 (17)0.0129 (6)
C20.1319 (4)0.7497 (3)0.48000 (17)0.0137 (6)
C30.0698 (4)0.7320 (3)0.39909 (17)0.0150 (7)
H30.02240.78850.37180.018*
C40.0777 (4)0.6295 (3)0.35772 (17)0.0161 (7)
C50.1450 (4)0.5472 (3)0.39550 (17)0.0157 (7)
H50.14840.47770.36600.019*
C60.2099 (4)0.5664 (3)0.47917 (17)0.0125 (6)
C70.2743 (4)0.4742 (3)0.51432 (18)0.0142 (6)
H70.26420.40610.47990.017*
C80.3973 (4)0.3788 (3)0.61884 (18)0.0134 (6)
C90.3827 (4)0.2740 (3)0.57325 (19)0.0172 (7)
H90.33610.26430.51740.021*
C100.4360 (4)0.1849 (3)0.60964 (19)0.0191 (7)
H100.42720.11390.57880.023*
C110.5026 (5)0.1987 (3)0.69131 (19)0.0217 (7)
H110.53670.13610.71590.026*
C120.5201 (4)0.3013 (3)0.73727 (19)0.0184 (7)
H120.56670.30970.79310.022*
C130.4690 (4)0.3924 (3)0.70124 (18)0.0139 (6)
C140.5440 (4)0.5275 (3)0.81769 (17)0.0149 (7)
H140.58030.46820.84570.018*
C150.5606 (4)0.6358 (3)0.86300 (17)0.0147 (7)
C160.6296 (4)0.6425 (3)0.94604 (17)0.0168 (7)
H160.66000.57710.96800.020*
C170.6526 (4)0.7431 (3)0.99485 (17)0.0172 (7)
C180.6111 (4)0.8407 (3)0.96363 (18)0.0174 (7)
H180.62800.91040.99760.021*
C190.5458 (4)0.8344 (3)0.88351 (18)0.0156 (7)
C200.5124 (4)0.7327 (3)0.82895 (17)0.0142 (7)
O30.7162 (3)0.69177 (19)0.64181 (13)0.0218 (5)
N30.8292 (4)0.8852 (2)0.68559 (16)0.0251 (7)
C210.8417 (5)0.7771 (3)0.6803 (2)0.0272 (8)
H210.95560.76280.70810.033*
C220.6627 (5)0.9150 (3)0.6398 (2)0.0278 (8)
H22A0.57530.84470.60820.033*
H22B0.70520.97190.60430.033*
H22C0.59670.94830.67650.033*
C230.9791 (6)0.9809 (3)0.7305 (3)0.0478 (12)
H23A1.08060.95120.75970.057*
H23B0.92731.02330.76820.057*
H23C1.03151.03330.69410.057*
O41.225 (3)0.6119 (8)1.0649 (3)0.0317 (16)0.741 (4)
C241.1892 (7)0.7023 (4)1.0473 (2)0.0281 (12)0.741 (4)
H241.20900.76321.08910.034*0.741 (4)
N41.1242 (16)0.7216 (4)0.9731 (2)0.0216 (12)0.741 (4)
C251.0952 (8)0.8347 (4)0.9571 (4)0.0382 (14)0.741 (4)
H25A1.10950.88281.00750.046*0.741 (4)
H25B0.96650.82430.92540.046*0.741 (4)
H25C1.19000.87290.92760.046*0.741 (4)
C261.0890 (7)0.6327 (4)0.9057 (3)0.0340 (13)0.741 (4)
H26A1.12860.56490.92400.041*0.741 (4)
H26B1.16220.66370.86630.041*0.741 (4)
H26C0.95250.60950.88150.041*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)
H24'1.12720.54340.94290.022*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)
H25D1.14220.76180.84530.026*0.259 (4)
H25E0.93120.73830.86300.026*0.259 (4)
H25F1.01380.63140.83950.026*0.259 (4)
C26'1.1704 (18)0.8156 (10)1.0052 (7)0.019 (3)0.259 (4)
H26D1.05410.84071.00700.023*0.259 (4)
H26E1.26130.87560.98540.023*0.259 (4)
H26F1.22800.80341.05870.023*0.259 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0175 (2)0.01176 (19)0.01046 (18)0.00541 (16)0.00143 (15)0.00295 (15)
Br10.02559 (19)0.01350 (16)0.02113 (17)0.00819 (14)0.00104 (14)0.00254 (13)
Br20.02115 (18)0.0359 (2)0.01140 (16)0.00857 (15)−0.00079 (13)0.00359 (14)
Br30.02659 (19)0.0333 (2)0.01011 (16)0.00644 (15)0.00017 (14)0.00550 (14)
Br40.0337 (2)0.01807 (17)0.01618 (16)0.01086 (15)0.00296 (14)0.00318 (13)
O10.0191 (12)0.0135 (11)0.0094 (10)0.0063 (9)−0.0006 (9)0.0018 (9)
O20.0226 (12)0.0148 (11)0.0090 (10)0.0081 (10)0.0009 (9)0.0018 (9)
N10.0110 (13)0.0112 (13)0.0143 (13)0.0025 (10)0.0010 (11)0.0016 (11)
N20.0157 (14)0.0127 (13)0.0164 (13)0.0049 (11)0.0060 (11)0.0050 (11)
C10.0115 (15)0.0142 (16)0.0120 (15)0.0013 (12)0.0015 (12)0.0045 (13)
C20.0134 (16)0.0121 (15)0.0160 (16)0.0029 (12)0.0038 (13)0.0035 (13)
C30.0103 (15)0.0182 (17)0.0167 (16)0.0031 (13)0.0013 (13)0.0080 (13)
C40.0119 (16)0.0222 (18)0.0114 (15)0.0017 (13)−0.0014 (13)0.0032 (14)
C50.0166 (17)0.0175 (17)0.0127 (15)0.0043 (13)0.0039 (13)−0.0017 (13)
C60.0146 (16)0.0131 (16)0.0118 (15)0.0057 (13)0.0043 (13)0.0027 (13)
C70.0143 (16)0.0127 (16)0.0160 (16)0.0014 (13)0.0070 (13)0.0017 (13)
C80.0093 (15)0.0114 (15)0.0209 (16)0.0021 (12)0.0058 (13)0.0060 (13)
C90.0149 (16)0.0156 (16)0.0202 (17)0.0039 (13)0.0013 (14)0.0027 (14)
C100.0188 (17)0.0125 (16)0.0267 (18)0.0047 (14)0.0064 (15)0.0015 (14)
C110.0241 (19)0.0177 (17)0.0294 (19)0.0095 (14)0.0117 (15)0.0127 (15)
C120.0197 (17)0.0226 (18)0.0181 (17)0.0098 (14)0.0088 (14)0.0086 (14)
C130.0145 (16)0.0113 (15)0.0179 (16)0.0041 (12)0.0064 (13)0.0031 (13)
C140.0146 (16)0.0183 (17)0.0144 (15)0.0055 (13)0.0049 (13)0.0094 (13)
C150.0122 (16)0.0202 (17)0.0120 (15)0.0049 (13)0.0017 (13)0.0029 (13)
C160.0147 (16)0.0237 (18)0.0150 (16)0.0085 (14)0.0028 (13)0.0101 (14)
C170.0158 (17)0.0257 (18)0.0085 (15)0.0039 (14)0.0001 (13)0.0027 (14)
C180.0152 (17)0.0217 (18)0.0151 (16)0.0047 (14)0.0036 (13)0.0003 (14)
C190.0168 (17)0.0161 (16)0.0159 (16)0.0066 (13)0.0042 (13)0.0049 (13)
C200.0113 (16)0.0193 (17)0.0127 (15)0.0041 (13)0.0034 (12)0.0037 (13)
O30.0247 (13)0.0146 (12)0.0243 (13)0.0014 (10)0.0073 (11)−0.0015 (10)
N30.0296 (17)0.0163 (15)0.0258 (16)0.0010 (13)0.0043 (13)−0.0002 (13)
C210.030 (2)0.029 (2)0.0271 (19)0.0131 (17)0.0084 (17)0.0096 (17)
C220.036 (2)0.0224 (19)0.0259 (19)0.0092 (17)0.0055 (17)0.0013 (16)
C230.047 (3)0.023 (2)0.057 (3)−0.0038 (19)−0.012 (2)−0.001 (2)
O40.0336 (19)0.031 (2)0.029 (3)0.0112 (18)−0.003 (4)0.011 (2)
C240.021 (3)0.032 (3)0.027 (3)0.004 (2)−0.002 (2)0.006 (2)
N40.0193 (16)0.021 (2)0.024 (3)0.005 (2)0.001 (4)0.007 (2)
C250.030 (3)0.035 (3)0.056 (4)0.012 (3)0.014 (3)0.023 (3)
C260.024 (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, °) top
Cu1—O11.910 (2)C16—C171.372 (4)
Cu1—O21.9174 (19)C16—H160.95
Cu1—N11.954 (2)C17—C181.397 (4)
Cu1—N21.958 (2)C18—C191.367 (4)
Cu1—O32.501 (2)C18—H180.95
Br1—C21.894 (3)C19—C201.423 (4)
Br2—C41.911 (3)O3—C211.247 (4)
Br3—C171.897 (3)N3—C211.316 (4)
Br4—C191.901 (3)N3—C231.441 (4)
O1—C11.295 (3)N3—C221.471 (4)
O2—C201.294 (3)C21—H210.95
N1—C71.291 (4)C22—H22A0.98
N1—C81.416 (4)C22—H22B0.98
N2—C141.293 (4)C22—H22C0.98
N2—C131.426 (4)C23—H23A0.98
C1—C21.418 (4)C23—H23B0.98
C1—C61.423 (4)C23—H23C0.98
C2—C31.369 (4)O4—C241.218 (3)
C3—C41.390 (4)C24—N41.340 (3)
C3—H30.95C24—H240.95
C4—C51.361 (4)N4—C261.456 (3)
C5—C61.416 (4)N4—C251.457 (3)
C5—H50.95C25—H25A0.98
C6—C71.434 (4)C25—H25B0.98
C7—H70.95C25—H25C0.98
C8—C91.399 (4)C26—H26A0.98
C8—C131.405 (4)C26—H26B0.98
C9—C101.377 (4)C26—H26C0.98
C9—H90.95O4'—C24'1.220 (3)
C10—C111.387 (4)C24'—N4'1.340 (3)
C10—H100.95C24'—H24'0.95
C11—C121.375 (4)N4'—C25'1.460 (3)
C11—H110.95N4'—C26'1.460 (3)
C12—C131.389 (4)C25'—H25D0.98
C12—H120.95C25'—H25E0.98
C14—C151.428 (4)C25'—H25F0.98
C14—H140.95C26'—H26D0.98
C15—C161.418 (4)C26'—H26E0.98
C15—C201.427 (4)C26'—H26F0.98
O1—Cu1—O289.11 (8)C16—C15—C14115.6 (3)
O1—Cu1—N193.40 (9)C20—C15—C14123.6 (3)
O2—Cu1—N1177.19 (10)C17—C16—C15120.3 (3)
O1—Cu1—N2170.18 (10)C17—C16—H16119.9
O2—Cu1—N293.64 (9)C15—C16—H16119.9
N1—Cu1—N283.67 (10)C16—C17—C18120.7 (3)
O1—Cu1—O396.00 (9)C16—C17—Br3119.8 (2)
O2—Cu1—O389.70 (8)C18—C17—Br3119.4 (2)
N1—Cu1—O391.29 (9)C19—C18—C17119.0 (3)
N2—Cu1—O393.44 (9)C19—C18—H18120.5
C1—O1—Cu1126.73 (19)C17—C18—H18120.5
C20—O2—Cu1126.9 (2)C18—C19—C20124.0 (3)
C7—N1—C8121.5 (3)C18—C19—Br4118.1 (2)
C7—N1—Cu1125.3 (2)C20—C19—Br4117.9 (2)
C8—N1—Cu1113.22 (19)O2—C20—C19119.9 (3)
C14—N2—C13121.4 (3)O2—C20—C15124.9 (3)
C14—N2—Cu1125.7 (2)C19—C20—C15115.2 (3)
C13—N2—Cu1112.92 (19)C21—O3—Cu1126.8 (2)
O1—C1—C2119.9 (3)C21—N3—C23123.2 (3)
O1—C1—C6125.0 (3)C21—N3—C22120.3 (3)
C2—C1—C6115.1 (3)C23—N3—C22116.3 (3)
C3—C2—C1123.8 (3)O3—C21—N3125.4 (3)
C3—C2—Br1118.3 (2)O3—C21—H21117.3
C1—C2—Br1117.8 (2)N3—C21—H21117.3
C2—C3—C4118.6 (3)N3—C22—H22A109.5
C2—C3—H3120.7N3—C22—H22B109.5
C4—C3—H3120.7H22A—C22—H22B109.5
C5—C4—C3121.8 (3)N3—C22—H22C109.5
C5—C4—Br2119.8 (2)H22A—C22—H22C109.5
C3—C4—Br2118.5 (2)H22B—C22—H22C109.5
C4—C5—C6119.3 (3)N3—C23—H23A109.5
C4—C5—H5120.3N3—C23—H23B109.5
C6—C5—H5120.3H23A—C23—H23B109.5
C5—C6—C1121.4 (3)N3—C23—H23C109.5
C5—C6—C7115.7 (3)H23A—C23—H23C109.5
C1—C6—C7123.0 (3)H23B—C23—H23C109.5
N1—C7—C6125.4 (3)O4—C24—N4124.5 (4)
N1—C7—H7117.3O4—C24—H24117.8
C6—C7—H7117.3N4—C24—H24117.8
C9—C8—C13119.4 (3)C24—N4—C26121.2 (4)
C9—C8—N1125.2 (3)C24—N4—C25120.7 (4)
C13—C8—N1115.3 (3)C26—N4—C25118.0 (4)
C10—C9—C8119.8 (3)O4'—C24'—N4'126.4 (14)
C10—C9—H9120.1O4'—C24'—H24'116.8
C8—C9—H9120.1N4'—C24'—H24'116.8
C9—C10—C11120.1 (3)C24'—N4'—C25'122.5 (11)
C9—C10—H10119.9C24'—N4'—C26'119.9 (11)
C11—C10—H10119.9C25'—N4'—C26'117.5 (10)
C12—C11—C10121.2 (3)N4'—C25'—H25D109.5
C12—C11—H11119.4N4'—C25'—H25E109.5
C10—C11—H11119.4H25D—C25'—H25E109.5
C11—C12—C13119.3 (3)N4'—C25'—H25F109.5
C11—C12—H12120.3H25D—C25'—H25F109.5
C13—C12—H12120.3H25E—C25'—H25F109.5
C12—C13—C8120.1 (3)N4'—C26'—H26D109.5
C12—C13—N2125.0 (3)N4'—C26'—H26E109.5
C8—C13—N2114.8 (3)H26D—C26'—H26E109.5
N2—C14—C15125.1 (3)N4'—C26'—H26F109.5
N2—C14—H14117.4H26D—C26'—H26F109.5
C15—C14—H14117.4H26E—C26'—H26F109.5
C16—C15—C20120.8 (3)
O2—Cu1—O1—C1169.2 (2)C8—C9—C10—C110.5 (5)
N1—Cu1—O1—C1−12.0 (2)C9—C10—C11—C12−1.2 (5)
O3—Cu1—O1—C179.6 (2)C10—C11—C12—C130.4 (5)
O1—Cu1—O2—C20171.6 (2)C11—C12—C13—C81.0 (5)
N2—Cu1—O2—C201.1 (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—C79.3 (3)N1—C8—C13—C12178.3 (3)
N2—Cu1—N1—C7179.9 (3)C9—C8—C13—N2178.1 (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—C892.6 (2)C14—N2—C13—C8178.7 (3)
O2—Cu1—N2—C141.5 (3)Cu1—N2—C13—C81.3 (3)
N1—Cu1—N2—C14−177.6 (3)C13—N2—C14—C15−179.1 (3)
O3—Cu1—N2—C1491.5 (3)Cu1—N2—C14—C15−2.0 (4)
O2—Cu1—N2—C13178.8 (2)N2—C14—C15—C16179.7 (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—C17179.3 (3)
Cu1—O1—C1—C68.9 (4)C15—C16—C17—C18−0.9 (5)
O1—C1—C2—C3179.9 (3)C15—C16—C17—Br3−179.6 (2)
C6—C1—C2—C3−1.0 (5)C16—C17—C18—C190.4 (5)
O1—C1—C2—Br11.0 (4)Br3—C17—C18—C19179.2 (2)
C6—C1—C2—Br1−179.9 (2)C17—C18—C19—C201.5 (5)
C1—C2—C3—C40.7 (5)C17—C18—C19—Br4−179.2 (2)
Br1—C2—C3—C4179.6 (2)Cu1—O2—C20—C19177.6 (2)
C2—C3—C4—C50.0 (5)Cu1—O2—C20—C15−3.4 (4)
C2—C3—C4—Br2−179.4 (2)C18—C19—C20—O2176.3 (3)
C3—C4—C5—C6−0.3 (5)Br4—C19—C20—O2−3.0 (4)
Br2—C4—C5—C6179.1 (2)C18—C19—C20—C15−2.8 (5)
C4—C5—C6—C10.0 (5)Br4—C19—C20—C15177.9 (2)
C4—C5—C6—C7178.6 (3)C16—C15—C20—O2−176.8 (3)
O1—C1—C6—C5179.7 (3)C14—C15—C20—O23.3 (5)
C2—C1—C6—C50.6 (4)C16—C15—C20—C192.3 (4)
O1—C1—C6—C71.1 (5)C14—C15—C20—C19−177.6 (3)
C2—C1—C6—C7−177.9 (3)O1—Cu1—O3—C2194.1 (3)
C8—N1—C7—C6177.3 (3)O2—Cu1—O3—C215.0 (3)
Cu1—N1—C7—C6−3.4 (4)N1—Cu1—O3—C21−172.4 (3)
C5—C6—C7—N1177.4 (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—C91.1 (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—C260.4 (17)
Cu1—N1—C8—C131.6 (3)O4—C24—N4—C25−176.8 (12)
C13—C8—C9—C100.9 (5)O4'—C24'—N4'—C25'177 (4)
N1—C8—C9—C10−179.1 (3)O4'—C24'—N4'—C26'1(6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O3i0.952.473.319 (4)148
C7—H7···O3i0.952.373.243 (4)153
C14—H14···O4ii0.952.333.226 (14)156
C22—H22A···O10.982.543.378 (4)143
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+2.
Table 1
Selected geometric parameters (Å) top
Cu1—O11.910 (2)Cu1—N21.958 (2)
Cu1—O21.9174 (19)Cu1—O32.501 (2)
Cu1—N11.954 (2)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O3i0.952.473.319 (4)148
C7—H7···O3i0.952.373.243 (4)153
C14—H14···O4ii0.952.333.226 (14)156
C22—H22A···O10.982.543.378 (4)143
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+2.
Acknowledgements top

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
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.