[(E)-2-(3,5-Dibromo-2-oxidobenzyl­ideneamino)-3-(4-hydroxy­phen­yl)propionato-κ3
               O,N,O′](dimethyl­formamide-κO)copper(II)

doi:10.1107/S1600536808007915

Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): m601–m602.

Published online 2008 March 29. doi: 10.1107/S1600536808007915

PMCID: PMC2961003

[(E)-2-(3,5-Dibromo-2-oxidobenzylideneamino)-3-(4-hydroxyphenyl)propionato-κ³ O,N,O′](dimethylformamide-κO)copper(II)

Ming-Xiong Tan,^a^b^* Zhen-Feng Chen,^c Zhou Neng,^b and Hong Liang^a

^aCollege of Chemistry and Chemical Engineering, Central South University, Changsha, HuNan 410083, People’s Republic of China

^bDepartment of Chemistry and Biology, Yu Lin Normal College, Yulin, Guangxi 537000, People’s Republic of China

^cKey Laboratory of Medicinal Chemical Resources and Molecular Engineering, Ministry of Education, College of Chemistry and Chemical Engineering, Guangxi Normal University, Yucai Road 15, Guilin 541004, People’s Republic of China

Correspondence e-mail: tanmx00/at/163.com

Received February 28, 2008; Accepted March 24, 2008.

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Abstract

In the title complex, [Cu(C₁₆H₁₁Br₂NO₄)(C₃H₇NO)]₂, there are two unique molecules in the asymmetric unit. Each Cu^II atom is coordinated by two O atoms and one N atom from the tridentate ligand L ²⁻ [LH₂ = (E)-2-(3,5-dibromo-2-hydroxybenzylideneamino)-2-(4-hydroxyphenyl)acetic acid] and the O atom of a dimethylformamide molecule to give a slightly distorted square-planar geometry. The two unique molecules form a dimer through weak C—H (...)

O hydrogen bonds. In the dimer, the Cu (...)

Cu distance is 3.712 (1) Å. In the crystal structure, molecules form a one-dimensional chain through C—H (...)

O hydrogen bonds. These are further aggregated into a three-dimensional network by O—H (...)

O and C—H

O hydrogen bonds.

Related literature

For related structures, see: Li et al. 2008

; Zhang et al. (2007a

). For preparative procedures, see: Xia et al. (2007

); Liu et al. (2007

An external file that holds a picture, illustration, etc.
Object name is e-64-0m601-scheme1.jpg Object name is e-64-0m601-scheme1.jpg

Experimental

Crystal data

[Cu(C₁₆H₁₁Br₂NO₄)(C₃H₇NO)]
M _r = 577.71
Triclinic,
a = 11.4316 (19) Å
b = 11.840 (2) Å
c = 15.984 (2) Å
α = 88.998 (3)°
β = 83.562 (2)°
γ = 73.210 (2)°
V = 2057.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 4.98 mm⁻¹
T = 298 (2) K
0.33 × 0.18 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick,1996 ) T _min = 0.267, T _max = 0.498
10763 measured reflections
7143 independent reflections
3697 reflections with > 2s(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.093
S = 1.00
7143 reflections
523 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Data collection: SMART (Bruker, 2001

); cell refinement: SAINT (Bruker, 2001

); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008

); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008

); molecular graphics: SHELXTL (Sheldrick, 2008

); software used to prepare material for publication: SHELXTL.

Table 1

Selected geometric parameters (Å, °)

Table 2

Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007915/sj2468sup1.cif

Click here to view.^{(28K, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007915/sj2468Isup2.hkl

Click here to view.^{(349K, hkl)}

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

Acknowledgments

We acknowledge financial support by the NSFC (No. 20561001) and the EDF of Guangxi (No. 200607LX067).

supplementary crystallographic information

Comment

Herein, we report the structure of a new mononuclear copper coordination complex [Cu(L)(C₃H₇NO)]₂ (1), Fig. 1, of the chiral ligand (E)-2-(3,5-dibromo-2-oxidobenzylideneamino)-2-(4-hydroxyphenyl)acetate LH₂. The Cu(II) atom coordinates a dimethylformamide molecule and the tridentate anionic ligand L^2- which binds through the N atom and carboxylate and phenolate O atoms. Although the LH₂ ligand is chiral, the compound crystallizes as a racemate with two molecules in the asymmetric unit. The coordination geometry about each copper atom is slightly distorted square planar, Table 1. A s expected all other bond distances and angles are within normal ranges (Zhang et al., 2007a,b).

The two unique molecules form a dimer through weak C18—H18C···O7 and C37—H37C···O2 hydrogen bonds, Table 2. In the dimer, the Cu1···Cu2 distance is 3.712 (1) Å. In the crystal structure, molecules of (I) form a one-dimensional chain along c (Fig. 2) through C3–H3B···O8 and C22–H22B···O3 hydrogen bonds. These chains then form a three-dimensional network through O3—H3···O1 and O8—H8···O6 hydrogen bonds and C29–H29···O2 and C35—H35···O2 interactions (Table 2, Figure 3).

Experimental

Complex (I) was prepared following the procedure described by Liu et al. (2007) and Xia et al. (2007) as follows. 3,5-Dibromo-2-hydroxy-benzaldehyde(0.560 g, 2.0 mmol) and 4-hydroxyl-phenylalanine (0.3624 g, 2.0 mmol) were dissolved in 10 ml absolute methanol. The mixture was stirred for 1 h at room temperature to give a yellow solution. 2 ml DMF and 10 ml of a methanolic solution of CuSO₄.5H₂O (0.5 g, 2 mmol) were added, the mixture was refluxed for another 1 h at 363 K, and the resulting blue solution was filtered. Blue single crystals suitable for X–ray analysis were obtained by slow evaporation of the filtrate at room temperature. Yield: 80.1% (based on copper). Elemental analysis for [Cu(C₁₆H₁₁Br₂NO₄)(C₃H₇NO)]₂ calculated: C 46.69, H 3.71, N 5.73%; found: C 46.65, H 3.81, N 5.71%.

Figures

Fig. 1.

The asymmetric unit of (I), with 30% probability displacement ellipsoids for non-H atoms. Hydrogen atoms have been omitted and C—H···O hydrogen bonds are drawn as dashed lines.

Fig. 2.

The formation of one-dimensional chains along c. Hydrogen bonds are drawn as dashed lines.

Fig. 3.

Crystal packing of (I) showing the three-dimensional network, with hydrogen bonds drawn as dashed lines.

Crystal data

[Cu(C₁₆H₁₁Br₂NO₄)(C₃H₇NO)]	Z = 4
M_r = 577.71	F₀₀₀ = 1140
Triclinic, P1	D_x = 1.865 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 11.4316 (19) Å	Cell parameters from 1919 reflections
b = 11.840 (2) Å	θ = 2.2–21.6º
c = 15.984 (2) Å	µ = 4.98 mm⁻¹
α = 88.998 (3)º	T = 298 (2) K
β = 83.562 (2)º	Prism, blue
γ = 73.210 (2)º	0.33 × 0.18 × 0.14 mm
V = 2057.9 (6) Å³

Data collection

Bruker SMART CCD area-detector diffractometer	7143 independent reflections
Radiation source: fine-focus sealed tube	3697 reflections with > 2s(I)
Monochromator: graphite	R_int = 0.041
T = 298(2) K	θ_max = 25.0º
and ω scans	θ_min = 1.3º
Absorption correction: multi-scan(SADABS; Sheldrick,1996)	h = −13→13
T_min = 0.267, T_max = 0.498	k = −14→10
10763 measured reflections	l = −19→16

Refinement

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.024P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
7143 reflections	Δρ_max = 0.60 e Å⁻³
523 parameters	Δρ_min = −0.55 e Å⁻³
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Special details

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)

	x	y	z	U_iso*/U_eq
Cu1	0.45708 (7)	0.70847 (7)	0.17285 (5)	0.0437 (2)
Cu2	0.33188 (7)	0.52131 (7)	0.32557 (5)	0.0433 (2)
Br1	0.47185 (6)	0.32932 (7)	0.06179 (5)	0.0569 (2)
Br2	0.95715 (7)	0.15518 (7)	0.14381 (6)	0.0859 (3)
Br3	0.70303 (6)	0.51591 (6)	0.44153 (5)	0.0583 (2)
Br4	0.88589 (7)	0.02902 (7)	0.36347 (6)	0.0810 (3)
N1	0.6098 (5)	0.6878 (5)	0.2154 (3)	0.0386 (14)
N2	0.1415 (5)	0.6973 (6)	0.0891 (4)	0.0586 (17)
N3	0.3513 (4)	0.3622 (4)	0.2930 (3)	0.0312 (13)
N4	0.3335 (5)	0.8409 (5)	0.4121 (3)	0.0494 (15)
O1	0.4266 (4)	0.8725 (4)	0.2033 (3)	0.0507 (12)
O2	0.4951 (4)	0.9914 (4)	0.2783 (3)	0.0625 (14)
O3	0.7098 (4)	0.9130 (4)	−0.1456 (3)	0.0760 (16)
H3	0.6752	0.9822	−0.1549	0.114*
O4	0.4861 (4)	0.5476 (4)	0.1493 (3)	0.0492 (12)
O5	0.2972 (4)	0.7485 (4)	0.1347 (3)	0.0592 (14)
O6	0.1695 (4)	0.5527 (4)	0.2919 (3)	0.0509 (13)
O7	0.0475 (4)	0.4692 (4)	0.2348 (3)	0.0709 (16)
O8	0.0751 (4)	0.2943 (4)	0.6592 (3)	0.0816 (17)
H8	0.0063	0.3400	0.6711	0.122*
O9	0.4890 (4)	0.4905 (4)	0.3606 (3)	0.0431 (12)
O10	0.2976 (4)	0.6874 (4)	0.3510 (3)	0.0645 (15)
C1	0.5074 (7)	0.8940 (6)	0.2447 (4)	0.0443 (18)
C2	0.6249 (6)	0.7964 (6)	0.2492 (4)	0.0452 (18)
H2	0.6391	0.7842	0.3084	0.054*
C3	0.7327 (6)	0.8309 (6)	0.2023 (4)	0.0483 (18)
H3A	0.7399	0.9013	0.2289	0.058*
H3B	0.8077	0.7682	0.2079	0.058*
C4	0.7220 (5)	0.8543 (6)	0.1097 (4)	0.0390 (17)
C5	0.6648 (6)	0.9636 (6)	0.0814 (4)	0.0467 (18)
H5	0.6290	1.0245	0.1204	0.056*
C6	0.6584 (6)	0.9870 (6)	−0.0033 (4)	0.0492 (19)
H6	0.6202	1.0627	−0.0208	0.059*
C7	0.7089 (6)	0.8970 (6)	−0.0613 (5)	0.0450 (18)
C8	0.7654 (5)	0.7877 (6)	−0.0346 (4)	0.0458 (18)
H8A	0.8003	0.7271	−0.0740	0.055*
C9	0.7724 (5)	0.7642 (6)	0.0503 (4)	0.0394 (17)
H9	0.8107	0.6883	0.0674	0.047*
C10	0.6954 (6)	0.5907 (7)	0.2170 (4)	0.0427 (19)
H10	0.7636	0.5921	0.2432	0.051*
C11	0.6958 (6)	0.4798 (6)	0.1821 (4)	0.0339 (16)
C12	0.5917 (6)	0.4666 (6)	0.1476 (4)	0.0384 (17)
C13	0.6066 (6)	0.3563 (7)	0.1109 (4)	0.0434 (18)
C14	0.7127 (6)	0.2650 (6)	0.1096 (4)	0.0464 (18)
H14	0.7184	0.1930	0.0845	0.056*
C15	0.8119 (6)	0.2807 (6)	0.1461 (4)	0.0473 (19)
C16	0.8028 (6)	0.3859 (6)	0.1807 (4)	0.0451 (19)
H16	0.8697	0.3964	0.2043	0.054*
C17	0.2547 (7)	0.6760 (7)	0.1048 (5)	0.058 (2)
H17	0.3072	0.6007	0.0926	0.070*
C18	0.0959 (7)	0.6084 (7)	0.0547 (5)	0.083 (3)
H18A	0.1634	0.5397	0.0388	0.125*
H18B	0.0554	0.6387	0.0061	0.125*
H18C	0.0387	0.5877	0.0964	0.125*
C19	0.0575 (7)	0.8125 (8)	0.1092 (6)	0.117 (4)
H19A	0.0213	0.8142	0.1666	0.175*
H19B	−0.0061	0.8291	0.0724	0.175*
H19C	0.1011	0.8707	0.1021	0.175*
C20	0.1454 (6)	0.4640 (7)	0.2619 (4)	0.0453 (19)
C21	0.2437 (5)	0.3457 (5)	0.2600 (4)	0.0390 (17)
H21	0.2675	0.3202	0.2010	0.047*
C22	0.1966 (5)	0.2501 (5)	0.3067 (4)	0.0427 (17)
H22A	0.1238	0.2452	0.2829	0.051*
H22B	0.2588	0.1748	0.2964	0.051*
C23	0.1652 (6)	0.2694 (5)	0.4012 (4)	0.0349 (16)
C24	0.2473 (6)	0.2088 (5)	0.4556 (5)	0.0445 (18)
H24	0.3246	0.1613	0.4342	0.053*
C25	0.2147 (6)	0.2189 (6)	0.5402 (5)	0.0504 (19)
H25	0.2707	0.1775	0.5759	0.060*
C26	0.1029 (7)	0.2877 (6)	0.5744 (5)	0.0484 (19)
C27	0.0216 (6)	0.3516 (6)	0.5208 (4)	0.0488 (19)
H27	−0.0538	0.4022	0.5425	0.059*
C28	0.0536 (6)	0.3397 (6)	0.4346 (4)	0.0422 (18)
H28	−0.0023	0.3805	0.3987	0.051*
C29	0.4494 (6)	0.2781 (6)	0.2933 (4)	0.0387 (17)
H29	0.4508	0.2063	0.2698	0.046*
C30	0.5595 (6)	0.2846 (6)	0.3275 (4)	0.0354 (16)
C31	0.5709 (6)	0.3894 (6)	0.3605 (4)	0.0353 (16)
C32	0.6824 (6)	0.3771 (6)	0.3959 (4)	0.0431 (18)
C33	0.7748 (6)	0.2735 (7)	0.3965 (4)	0.050 (2)
H33	0.8461	0.2706	0.4205	0.060*
C34	0.7605 (6)	0.1727 (6)	0.3609 (4)	0.0479 (19)
C35	0.6547 (6)	0.1792 (6)	0.3273 (4)	0.0418 (18)
H35	0.6453	0.1116	0.3036	0.050*
C36	0.3602 (6)	0.7288 (6)	0.3940 (4)	0.0496 (19)
H36	0.4290	0.6775	0.4141	0.059*
C37	0.4104 (6)	0.8861 (6)	0.4608 (4)	0.063 (2)
H37A	0.4721	0.8213	0.4812	0.095*
H37B	0.3607	0.9322	0.5077	0.095*
H37C	0.4494	0.9346	0.4259	0.095*
C38	0.2263 (6)	0.9238 (6)	0.3835 (5)	0.075 (2)
H38A	0.1738	0.8816	0.3644	0.112*
H38B	0.2514	0.9687	0.3380	0.112*
H38C	0.1823	0.9761	0.4291	0.112*

Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0467 (5)	0.0381 (5)	0.0484 (6)	−0.0140 (4)	−0.0101 (4)	0.0016 (4)
Cu2	0.0440 (5)	0.0341 (5)	0.0536 (6)	−0.0120 (4)	−0.0116 (4)	0.0022 (4)
Br1	0.0556 (5)	0.0620 (6)	0.0605 (6)	−0.0290 (4)	−0.0039 (4)	−0.0116 (4)
Br2	0.0567 (5)	0.0566 (6)	0.1299 (9)	0.0036 (5)	−0.0036 (5)	0.0072 (5)
Br3	0.0577 (5)	0.0530 (5)	0.0742 (6)	−0.0261 (4)	−0.0222 (4)	0.0004 (4)
Br4	0.0546 (5)	0.0557 (6)	0.1204 (8)	0.0037 (5)	−0.0123 (5)	0.0119 (5)
N1	0.048 (4)	0.032 (4)	0.039 (4)	−0.015 (3)	−0.009 (3)	0.008 (3)
N2	0.037 (4)	0.065 (5)	0.074 (5)	−0.012 (4)	−0.016 (3)	0.002 (4)
N3	0.032 (3)	0.026 (3)	0.039 (4)	−0.012 (3)	−0.006 (3)	0.002 (2)
N4	0.056 (4)	0.044 (4)	0.048 (4)	−0.016 (4)	0.002 (3)	−0.003 (3)
O1	0.055 (3)	0.042 (3)	0.058 (3)	−0.017 (3)	−0.009 (3)	0.003 (2)
O2	0.084 (4)	0.044 (3)	0.065 (4)	−0.027 (3)	−0.008 (3)	−0.013 (3)
O3	0.108 (4)	0.059 (4)	0.041 (4)	0.007 (3)	−0.005 (3)	−0.003 (3)
O4	0.046 (3)	0.035 (3)	0.066 (3)	−0.007 (3)	−0.017 (2)	0.004 (2)
O5	0.050 (3)	0.055 (4)	0.073 (4)	−0.013 (3)	−0.014 (3)	−0.005 (3)
O6	0.046 (3)	0.042 (3)	0.066 (4)	−0.011 (3)	−0.015 (2)	0.004 (2)
O7	0.049 (3)	0.086 (4)	0.087 (4)	−0.027 (3)	−0.026 (3)	0.019 (3)
O8	0.098 (4)	0.078 (4)	0.041 (4)	0.017 (3)	−0.007 (3)	0.001 (3)
O9	0.048 (3)	0.031 (3)	0.051 (3)	−0.010 (2)	−0.008 (2)	0.001 (2)
O10	0.064 (3)	0.035 (3)	0.095 (4)	−0.005 (3)	−0.033 (3)	−0.002 (3)
C1	0.061 (5)	0.038 (5)	0.037 (5)	−0.021 (5)	−0.003 (4)	0.010 (4)
C2	0.064 (5)	0.049 (5)	0.035 (5)	−0.034 (4)	−0.014 (4)	0.004 (3)
C3	0.059 (5)	0.051 (5)	0.045 (5)	−0.028 (4)	−0.018 (4)	0.000 (3)
C4	0.039 (4)	0.041 (5)	0.046 (5)	−0.024 (4)	−0.007 (4)	−0.003 (4)
C5	0.072 (5)	0.032 (5)	0.037 (5)	−0.018 (4)	0.005 (4)	−0.006 (3)
C6	0.070 (5)	0.025 (4)	0.048 (5)	−0.008 (4)	−0.003 (4)	0.001 (4)
C7	0.046 (4)	0.044 (5)	0.041 (5)	−0.007 (4)	−0.002 (4)	−0.006 (4)
C8	0.045 (4)	0.044 (5)	0.044 (5)	−0.005 (4)	−0.006 (4)	−0.013 (4)
C9	0.038 (4)	0.033 (4)	0.053 (5)	−0.015 (4)	−0.014 (4)	0.002 (4)
C10	0.051 (5)	0.065 (6)	0.027 (4)	−0.036 (5)	−0.014 (4)	0.015 (4)
C11	0.037 (4)	0.032 (4)	0.038 (4)	−0.015 (4)	−0.013 (3)	0.009 (3)
C12	0.054 (5)	0.024 (4)	0.042 (5)	−0.018 (4)	−0.005 (4)	0.007 (3)
C13	0.037 (4)	0.058 (5)	0.043 (5)	−0.025 (4)	−0.006 (3)	0.008 (4)
C14	0.054 (5)	0.030 (5)	0.055 (5)	−0.016 (4)	0.006 (4)	−0.003 (3)
C15	0.045 (5)	0.036 (5)	0.061 (5)	−0.015 (4)	−0.003 (4)	0.012 (4)
C16	0.049 (5)	0.038 (5)	0.054 (5)	−0.022 (4)	−0.006 (4)	0.013 (4)
C17	0.044 (5)	0.067 (6)	0.058 (6)	−0.005 (5)	−0.011 (4)	0.014 (4)
C18	0.076 (6)	0.092 (7)	0.097 (8)	−0.038 (6)	−0.037 (5)	0.019 (5)
C19	0.059 (6)	0.116 (9)	0.169 (11)	−0.004 (6)	−0.033 (6)	−0.046 (7)
C20	0.035 (4)	0.055 (6)	0.046 (5)	−0.016 (5)	0.000 (4)	0.021 (4)
C21	0.042 (4)	0.049 (5)	0.034 (4)	−0.023 (4)	−0.011 (3)	−0.002 (3)
C22	0.045 (4)	0.040 (4)	0.051 (5)	−0.023 (4)	−0.011 (3)	−0.004 (3)
C23	0.039 (4)	0.029 (4)	0.044 (5)	−0.021 (4)	−0.005 (4)	−0.001 (3)
C24	0.037 (4)	0.034 (4)	0.058 (6)	−0.003 (4)	−0.007 (4)	−0.002 (4)
C25	0.050 (5)	0.043 (5)	0.054 (6)	−0.002 (4)	−0.017 (4)	0.005 (4)
C26	0.061 (5)	0.042 (5)	0.042 (5)	−0.014 (4)	−0.010 (4)	0.001 (4)
C27	0.041 (4)	0.050 (5)	0.048 (5)	−0.001 (4)	−0.009 (4)	0.008 (4)
C28	0.035 (4)	0.054 (5)	0.041 (5)	−0.014 (4)	−0.017 (4)	0.011 (4)
C29	0.049 (5)	0.033 (5)	0.035 (4)	−0.015 (4)	0.002 (4)	−0.007 (3)
C30	0.033 (4)	0.035 (4)	0.040 (4)	−0.013 (4)	−0.005 (3)	0.005 (3)
C31	0.039 (4)	0.036 (5)	0.038 (4)	−0.023 (4)	−0.001 (3)	0.002 (3)
C32	0.043 (4)	0.057 (5)	0.041 (5)	−0.033 (4)	−0.005 (4)	0.002 (4)
C33	0.039 (4)	0.051 (5)	0.062 (5)	−0.014 (4)	−0.013 (4)	0.014 (4)
C34	0.045 (5)	0.050 (5)	0.051 (5)	−0.021 (4)	0.001 (4)	0.008 (4)
C35	0.050 (5)	0.037 (5)	0.040 (5)	−0.017 (4)	0.004 (4)	−0.001 (3)
C36	0.057 (5)	0.030 (5)	0.057 (5)	−0.003 (4)	−0.011 (4)	0.006 (4)
C37	0.079 (6)	0.062 (5)	0.052 (5)	−0.027 (5)	−0.001 (4)	−0.013 (4)
C38	0.061 (5)	0.051 (6)	0.103 (7)	0.004 (5)	−0.024 (5)	−0.013 (5)

Geometric parameters (Å, °)

Cu1—O4	1.874 (4)	C10—C11	1.435 (8)
Cu1—N1	1.893 (5)	C10—H10	0.9300
Cu1—O5	1.917 (5)	C11—C16	1.393 (8)
Cu1—O1	1.932 (4)	C11—C12	1.415 (8)
Cu2—O9	1.874 (4)	C12—C13	1.398 (9)
Cu2—N3	1.907 (5)	C13—C14	1.371 (8)
Cu2—O6	1.922 (4)	C14—C15	1.391 (8)
Cu2—O10	1.932 (5)	C14—H14	0.9300
Br1—C13	1.912 (6)	C15—C16	1.344 (9)
Br2—C15	1.878 (7)	C16—H16	0.9300
Br3—C32	1.896 (6)	C17—H17	0.9300
Br4—C34	1.884 (7)	C18—H18A	0.9600
N1—C10	1.279 (7)	C18—H18B	0.9600
N1—C2	1.465 (7)	C18—H18C	0.9600
N2—C17	1.297 (8)	C19—H19A	0.9600
N2—C19	1.440 (9)	C19—H19B	0.9600
N2—C18	1.443 (8)	C19—H19C	0.9600
N3—C29	1.267 (6)	C20—C21	1.520 (8)
N3—C21	1.454 (6)	C21—C22	1.536 (7)
N4—C36	1.303 (8)	C21—H21	0.9800
N4—C38	1.446 (7)	C22—C23	1.518 (8)
N4—C37	1.451 (7)	C22—H22A	0.9700
O1—C1	1.278 (7)	C22—H22B	0.9700
O2—C1	1.245 (7)	C23—C28	1.362 (8)
O3—C7	1.358 (7)	C23—C24	1.387 (7)
O3—H3	0.8200	C24—C25	1.360 (8)
O4—C12	1.305 (7)	C24—H24	0.9300
O5—C17	1.228 (8)	C25—C26	1.361 (8)
O6—C20	1.274 (8)	C25—H25	0.9300
O7—C20	1.229 (7)	C26—C27	1.386 (8)
O8—C26	1.355 (7)	C27—C28	1.384 (8)
O8—H8	0.8200	C27—H27	0.9300
O9—C31	1.289 (6)	C28—H28	0.9300
O10—C36	1.245 (7)	C29—C30	1.449 (7)
C1—C2	1.506 (9)	C29—H29	0.9300
C2—C3	1.524 (8)	C30—C35	1.399 (8)
C2—H2	0.9800	C30—C31	1.403 (8)
C3—C4	1.513 (8)	C31—C32	1.421 (8)
C3—H3A	0.9700	C32—C33	1.368 (8)
C3—H3B	0.9700	C33—C34	1.391 (8)
C4—C5	1.366 (8)	C33—H33	0.9300
C4—C9	1.389 (8)	C34—C35	1.359 (8)
C5—C6	1.383 (8)	C35—H35	0.9300
C5—H5	0.9300	C36—H36	0.9300
C6—C7	1.373 (9)	C37—H37A	0.9600
C6—H6	0.9300	C37—H37B	0.9600
C7—C8	1.354 (8)	C37—H37C	0.9600
C8—C9	1.386 (8)	C38—H38A	0.9600
C8—H8A	0.9300	C38—H38B	0.9600
C9—H9	0.9300	C38—H38C	0.9600

O4—Cu1—N1	94.3 (2)	C11—C16—H16	119.1
O4—Cu1—O5	92.5 (2)	O5—C17—N2	124.5 (8)
N1—Cu1—O5	173.1 (2)	O5—C17—H17	117.8
O4—Cu1—O1	177.0 (2)	N2—C17—H17	117.8
N1—Cu1—O1	84.6 (2)	N2—C18—H18A	109.5
O5—Cu1—O1	88.5 (2)	N2—C18—H18B	109.5
O9—Cu2—N3	95.0 (2)	H18A—C18—H18B	109.5
O9—Cu2—O6	178.9 (2)	N2—C18—H18C	109.5
N3—Cu2—O6	85.1 (2)	H18A—C18—H18C	109.5
O9—Cu2—O10	90.9 (2)	H18B—C18—H18C	109.5
N3—Cu2—O10	173.7 (2)	N2—C19—H19A	109.5
O6—Cu2—O10	89.0 (2)	N2—C19—H19B	109.5
C10—N1—C2	120.1 (5)	H19A—C19—H19B	109.5
C10—N1—Cu1	126.0 (4)	N2—C19—H19C	109.5
C2—N1—Cu1	113.9 (4)	H19A—C19—H19C	109.5
C17—N2—C19	118.9 (7)	H19B—C19—H19C	109.5
C17—N2—C18	122.2 (7)	O7—C20—O6	123.6 (7)
C19—N2—C18	118.9 (6)	O7—C20—C21	118.7 (7)
C29—N3—C21	121.2 (5)	O6—C20—C21	117.7 (6)
C29—N3—Cu2	125.2 (4)	N3—C21—C20	108.7 (5)
C21—N3—Cu2	113.5 (4)	N3—C21—C22	112.6 (4)
C36—N4—C38	120.5 (6)	C20—C21—C22	112.3 (5)
C36—N4—C37	121.2 (6)	N3—C21—H21	107.7
C38—N4—C37	118.3 (6)	C20—C21—H21	107.7
C1—O1—Cu1	114.8 (4)	C22—C21—H21	107.7
C7—O3—H3	109.5	C23—C22—C21	115.3 (5)
C12—O4—Cu1	126.0 (4)	C23—C22—H22A	108.4
C17—O5—Cu1	123.4 (5)	C21—C22—H22A	108.4
C20—O6—Cu2	115.0 (4)	C23—C22—H22B	108.4
C26—O8—H8	109.5	C21—C22—H22B	108.4
C31—O9—Cu2	126.7 (4)	H22A—C22—H22B	107.5
C36—O10—Cu2	124.0 (4)	C28—C23—C24	118.5 (6)
O2—C1—O1	123.5 (7)	C28—C23—C22	121.2 (5)
O2—C1—C2	119.3 (7)	C24—C23—C22	120.1 (6)
O1—C1—C2	117.1 (6)	C25—C24—C23	119.9 (6)
N1—C2—C1	108.5 (6)	C25—C24—H24	120.0
N1—C2—C3	112.6 (6)	C23—C24—H24	120.0
C1—C2—C3	110.1 (5)	C24—C25—C26	122.1 (6)
N1—C2—H2	108.5	C24—C25—H25	118.9
C1—C2—H2	108.5	C26—C25—H25	118.9
C3—C2—H2	108.5	O8—C26—C25	119.7 (6)
C4—C3—C2	114.2 (5)	O8—C26—C27	121.8 (7)
C4—C3—H3A	108.7	C25—C26—C27	118.4 (7)
C2—C3—H3A	108.7	C28—C27—C26	119.5 (7)
C4—C3—H3B	108.7	C28—C27—H27	120.3
C2—C3—H3B	108.7	C26—C27—H27	120.3
H3A—C3—H3B	107.6	C23—C28—C27	121.4 (6)
C5—C4—C9	117.7 (6)	C23—C28—H28	119.3
C5—C4—C3	121.8 (6)	C27—C28—H28	119.3
C9—C4—C3	120.4 (6)	N3—C29—C30	125.3 (6)
C4—C5—C6	122.3 (6)	N3—C29—H29	117.4
C4—C5—H5	118.8	C30—C29—H29	117.4
C6—C5—H5	118.8	C35—C30—C31	121.0 (6)
C7—C6—C5	119.2 (6)	C35—C30—C29	116.3 (6)
C7—C6—H6	120.4	C31—C30—C29	122.7 (6)
C5—C6—H6	120.4	O9—C31—C30	124.6 (6)
C8—C7—O3	117.4 (6)	O9—C31—C32	120.7 (6)
C8—C7—C6	119.5 (7)	C30—C31—C32	114.7 (6)
O3—C7—C6	123.0 (6)	C33—C32—C31	124.1 (6)
C7—C8—C9	121.4 (6)	C33—C32—Br3	119.3 (5)
C7—C8—H8A	119.3	C31—C32—Br3	116.5 (5)
C9—C8—H8A	119.3	C32—C33—C34	119.0 (6)
C8—C9—C4	119.9 (6)	C32—C33—H33	120.5
C8—C9—H9	120.1	C34—C33—H33	120.5
C4—C9—H9	120.1	C35—C34—C33	119.2 (7)
N1—C10—C11	126.0 (6)	C35—C34—Br4	121.5 (6)
N1—C10—H10	117.0	C33—C34—Br4	119.3 (5)
C11—C10—H10	117.0	C34—C35—C30	121.9 (6)
C16—C11—C12	120.7 (6)	C34—C35—H35	119.0
C16—C11—C10	118.3 (6)	C30—C35—H35	119.0
C12—C11—C10	121.0 (6)	O10—C36—N4	122.9 (6)
O4—C12—C13	119.7 (6)	O10—C36—H36	118.5
O4—C12—C11	125.0 (6)	N4—C36—H36	118.5
C13—C12—C11	115.3 (6)	N4—C37—H37A	109.5
C14—C13—C12	123.3 (6)	N4—C37—H37B	109.5
C14—C13—Br1	117.9 (5)	H37A—C37—H37B	109.5
C12—C13—Br1	118.8 (5)	N4—C37—H37C	109.5
C13—C14—C15	119.5 (6)	H37A—C37—H37C	109.5
C13—C14—H14	120.2	H37B—C37—H37C	109.5
C15—C14—H14	120.2	N4—C38—H38A	109.5
C16—C15—C14	119.3 (6)	N4—C38—H38B	109.5
C16—C15—Br2	121.4 (6)	H38A—C38—H38B	109.5
C14—C15—Br2	119.2 (6)	N4—C38—H38C	109.5
C15—C16—C11	121.8 (7)	H38A—C38—H38C	109.5
C15—C16—H16	119.1	H38B—C38—H38C	109.5

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18C···O7	0.96	2.59	3.364 (9)	137
C37—H37C···O2	0.96	2.48	3.307 (8)	144
O3—H3···O1ⁱ	0.82	1.98	2.772 (6)	163
O8—H8···O6ⁱⁱ	0.82	2.07	2.888 (6)	176
C16—H16···O7ⁱⁱⁱ	0.93	2.52	3.422 (9)	163
C29—H29···O2^iv	0.93	2.45	3.291 (8)	150
C35—H35···O2^iv	0.93	2.59	3.408 (8)	147

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2468).

References

Bruker (2001). SAINT and SMART Bruker AXS Inc, Madison, Wisconsin, USA.
Li, G. Z., Zhang, S. H. & Liu, Z. (2008). Acta Cryst. E64, m52. [PMC free article] [PubMed]
Liu, Z., Zhang, S.-H., Feng, X.-Z., Li, G.-Z. & Lin, Y.-B. (2007). Acta Cryst. E63, m156–m158.
Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
Xia, J. H., Zhang, S.-H., Feng, X.-Z., Jin, L.-X. & Zheng, L. (2007). Acta Cryst. E63, m353–m355.
Zhang, S.-H., Feng, X.-Z., Li, G.-Z., Jing, L.-X. & Liu, Z. (2007a). Acta Cryst. E63, m1156–m1157.
Zhang, S.-H., Feng, X.-Z., Li, G.-Z., Jing, L.-X. & Liu, Z. (2007b). Acta Cryst. E63, m535–m536.

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