Bis[μ-N′-(5-bromo-3-meth­oxy-2-oxido­benzyl­idene)-2-hydroxybenzohydra­zidato]bis[(N,N-dimethyl­formamide)­copper(II)]

Zhao, S.; Li, L.; Liu, X.; Feng, W.; Lü, X.

doi:10.1107/S1600536812036100

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page m1216

doi:10.1107/S1600536812036100

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Bis[μ-N′-(5-bromo-3-methoxy-2-oxidobenzylidene)-2-hydroxybenzohydrazidato]bis[(N,N-dimethylformamide)copper(II)]

Shunsheng Zhao,^a ^* Lanlan Li,^a Xiangrong Liu,^a Weixu Feng ^b and Xingqiang Lü ^b

^aCollege of Chemistry and Chemical Engineering, Xi'an University of Science and Technology, Xi'an 710054, Shaanxi, People's Republic of China, and ^bCollege of Chemical Engineering, Northwest University, Xi'an 710069, Shaanxi, People's Republic of China
^*Correspondence e-mail: shshzhao@xust.edu.cn

(Received 5 August 2012; accepted 16 August 2012; online 25 August 2012)

The title compound, [Cu₂(C₁₅H₁₁BrN₂O₄)₂(C₃H₇NO)₂], is derived from the reaction of N′-(5-bromo-2-hydroxy-3-methoxybenzylidene)-2-hydroxybenzohydrazide and copper nitrate in a dimethylformamide solution in the presence of sodium hydroxide. The compound can be regarded as a binuclear centrosymmetric complex. In the crystal, the Cu^II atom is fivefold surrounded and adopts a distorted square-pyramidal coordination environment. An intramolecular O—H⋯N hydrogen bond stabilizes the molecular conformation.

Related literature

For the synthesis of N′-(5-bromo-2-hydroxy-3-methoxybenzylidene)-2-hydroxybenzohydrazide and its crystal structure, see: Zhao et al. (2012 ). For the crystal structure of a complex with a similar coordination environment, see: Huang et al. (2010 ).

Experimental

Crystal data

[Cu₂(C₁₅H₁₁BrN₂O₄)₂(C₃H₇NO)₂]
M_r = 999.61
Triclinic, $[P \overline 1]$
a = 8.3861 (17) Å
b = 9.5795 (19) Å
c = 12.275 (3) Å
α = 90.446 (3)°
β = 97.850 (3)°
γ = 101.688 (3)°
V = 956.0 (3) Å³
Z = 1
Mo Kα radiation
μ = 3.27 mm⁻¹
T = 296 K
0.38 × 0.25 × 0.16 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.371, T_max = 0.620
5880 measured reflections
4354 independent reflections
2957 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.123
S = 0.99
4354 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯N2	0.82	1.84	2.566 (3)	146

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 and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812036100/bt5995sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812036100/bt5995Isup2.hkl

checkCIF report

Comment top

Hydrazones attract the interest of researchers due to their various biological activities and their capacity for chelating to most kind of metals. As Fig. 1 shows, the Cu_II ion exists in a distorted square-pyramidal coordination geometry and it is located in the center of the coordination basal plane, which is defined by three donor atoms (O2, N1 and O3) of the hydrozone ligand and O5 atom from the DMF molecule with a mean plane deviation of 0.0367 (4) Å. The axial position is occupied by O3 atom from another asymmetric unit. The molecular conformation is stabilized by an intramolecular O—H···N hydrogen bond (Table 1).

Related literature top

For the synthesis of N'-(5-bromo-2-hydroxy-3-methoxybenzylidene)-2-hydroxybenzohydrazide and its crystal structure, see: Zhao et al. (2012). For the crystal structure of a complex with a similar coordination environment, see: Huang et al. (2010).

Experimental top

A solution of copper nitrate (186.2 mg, 1.0 mmol) in DMF (2 ml) was added to a solution of N'-(5-bromo-2-hydroxy-3-methoxybenzylidene)-2-hydroxybenzohydrazide (361.5 mg, 1.0 mmol) in DMF (10 ml) and stirred at room temperature for 2 h before being filtered. The dark green filtrate was allow to evaperate slowly in the air for several days. Green crystals was collected by filtration and dried under vacumn, yield 59.3%.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 and local programs.

Figures top

Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.

Bis[µ-N'-(5-bromo-3-methoxy-2- oxidobenzylidene)-2-hydroxybenzohydrazidato]bis[(N,N- dimethylformamide)copper(II)] top

Crystal data top

[Cu₂(C₁₅H₁₁BrN₂O₄)₂(C₃H₇NO)₂]	Z = 1
M_r = 999.61	F(000) = 502
Triclinic, P1	D_x = 1.736 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3861 (17) Å	Cell parameters from 3650 reflections
b = 9.5795 (19) Å	θ = 1.8–26.5°
c = 12.275 (3) Å	µ = 3.27 mm⁻¹
α = 90.446 (3)°	T = 296 K
β = 97.850 (3)°	Block, green
γ = 101.688 (3)°	0.38 × 0.25 × 0.16 mm
V = 956.0 (3) Å³

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	4354 independent reflections
Radiation source: fine-focus sealed tube	2957 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
thin–slice ω scans	θ_max = 29.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→9
T_min = 0.371, T_max = 0.620	k = −13→9
5880 measured reflections	l = −15→16

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.069P)²] where P = (F_o² + 2F_c²)/3
4354 reflections	(Δ/σ)_max = 0.001
256 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

[Cu₂(C₁₅H₁₁BrN₂O₄)₂(C₃H₇NO)₂]	γ = 101.688 (3)°
M_r = 999.61	V = 956.0 (3) Å³
Triclinic, P1	Z = 1
a = 8.3861 (17) Å	Mo Kα radiation
b = 9.5795 (19) Å	µ = 3.27 mm⁻¹
c = 12.275 (3) Å	T = 296 K
α = 90.446 (3)°	0.38 × 0.25 × 0.16 mm
β = 97.850 (3)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	4354 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2957 reflections with I > 2σ(I)
T_min = 0.371, T_max = 0.620	R_int = 0.022
5880 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 0.99	Δρ_max = 0.59 e Å⁻³
4354 reflections	Δρ_min = −0.58 e Å⁻³
256 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
Cu1	0.08579 (5)	0.69096 (4)	1.00600 (3)	0.04176 (15)
Br1	−0.38768 (6)	1.16095 (5)	1.23139 (4)	0.0821 (2)
O2	0.1023 (3)	0.8271 (2)	1.11968 (18)	0.0456 (6)
O3	0.0529 (3)	0.5575 (2)	0.88176 (17)	0.0472 (6)
N1	−0.1145 (3)	0.7314 (3)	0.9327 (2)	0.0383 (6)
C8	−0.1977 (4)	0.8182 (4)	0.9650 (3)	0.0435 (8)
H8A	−0.2920	0.8293	0.9194	0.052*
N2	−0.1691 (3)	0.6616 (3)	0.8310 (2)	0.0397 (6)
O4	−0.3540 (3)	0.5853 (3)	0.6472 (2)	0.0592 (7)
H4A	−0.3231	0.6295	0.7064	0.089*
O1	0.1737 (3)	0.9882 (3)	1.29675 (19)	0.0532 (6)
C7	−0.0064 (4)	0.8995 (3)	1.1382 (2)	0.0373 (7)
C5	−0.2652 (4)	0.9817 (4)	1.0956 (3)	0.0473 (8)
H5A	−0.3618	0.9825	1.0485	0.057*
C2	0.0244 (4)	0.9885 (4)	1.2357 (3)	0.0427 (8)
C15	−0.0090 (4)	0.4028 (4)	0.6826 (3)	0.0503 (9)
H15A	0.0814	0.3948	0.7334	0.060*
C9	−0.0709 (4)	0.5740 (3)	0.8131 (2)	0.0378 (7)
C10	−0.1099 (4)	0.4926 (3)	0.7074 (3)	0.0404 (7)
C3	−0.0851 (4)	1.0652 (4)	1.2625 (3)	0.0463 (8)
H3A	−0.0634	1.1207	1.3274	0.056*
C13	−0.1735 (5)	0.3340 (5)	0.5115 (3)	0.0665 (11)
H13A	−0.1945	0.2805	0.4456	0.080*
C11	−0.2471 (4)	0.5005 (4)	0.6306 (3)	0.0442 (8)
C4	−0.2312 (5)	1.0593 (4)	1.1908 (3)	0.0501 (9)
C12	−0.2778 (5)	0.4198 (4)	0.5330 (3)	0.0595 (10)
H12A	−0.3695	0.4240	0.4822	0.071*
C6	−0.1546 (4)	0.8990 (3)	1.0669 (3)	0.0396 (7)
C14	−0.0388 (5)	0.3255 (5)	0.5852 (3)	0.0641 (11)
H14A	0.0322	0.2676	0.5694	0.077*
O5	0.2998 (3)	0.6509 (2)	1.06249 (19)	0.0480 (6)
N3	0.5109 (3)	0.6665 (3)	1.1985 (2)	0.0469 (7)
C17	0.3796 (4)	0.7041 (4)	1.1530 (3)	0.0456 (8)
H17A	0.3414	0.7742	1.1886	0.055*
C16	0.6002 (5)	0.7336 (5)	1.3018 (3)	0.0617 (11)
H16A	0.5433	0.8023	1.3272	0.093*
H16B	0.7090	0.7806	1.2907	0.093*
H16C	0.6073	0.6622	1.3557	0.093*
C1	0.2101 (6)	1.0583 (5)	1.4017 (3)	0.0672 (11)
H1A	0.3178	1.0496	1.4351	0.101*
H1B	0.1304	1.0154	1.4472	0.101*
H1C	0.2066	1.1573	1.3941	0.101*
C18	0.5749 (5)	0.5542 (5)	1.1512 (4)	0.0654 (11)
H18A	0.4883	0.4937	1.1028	0.098*
H18B	0.6171	0.4988	1.2089	0.098*
H18C	0.6616	0.5955	1.1104	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0362 (2)	0.0507 (3)	0.0374 (2)	0.01501 (18)	−0.00696 (16)	−0.00787 (17)
Br1	0.0733 (3)	0.1088 (4)	0.0734 (3)	0.0549 (3)	−0.0096 (2)	−0.0330 (3)
O2	0.0385 (13)	0.0546 (14)	0.0435 (12)	0.0180 (11)	−0.0066 (10)	−0.0112 (10)
O3	0.0419 (13)	0.0591 (15)	0.0408 (12)	0.0209 (11)	−0.0079 (10)	−0.0123 (10)
N1	0.0389 (15)	0.0411 (15)	0.0336 (13)	0.0104 (12)	−0.0023 (11)	−0.0008 (11)
C8	0.0374 (17)	0.046 (2)	0.0449 (18)	0.0123 (15)	−0.0077 (14)	−0.0012 (15)
N2	0.0387 (15)	0.0393 (15)	0.0375 (14)	0.0080 (12)	−0.0067 (11)	−0.0072 (11)
O4	0.0599 (16)	0.0672 (18)	0.0486 (15)	0.0250 (14)	−0.0163 (12)	−0.0091 (12)
O1	0.0450 (14)	0.0676 (17)	0.0441 (13)	0.0160 (12)	−0.0094 (11)	−0.0157 (12)
C7	0.0384 (17)	0.0368 (17)	0.0360 (16)	0.0086 (14)	0.0018 (13)	−0.0004 (13)
C5	0.0402 (19)	0.059 (2)	0.0440 (19)	0.0185 (16)	−0.0023 (15)	−0.0039 (16)
C2	0.0405 (18)	0.048 (2)	0.0374 (17)	0.0088 (15)	−0.0014 (14)	−0.0027 (14)
C15	0.043 (2)	0.061 (2)	0.047 (2)	0.0170 (17)	−0.0022 (15)	−0.0081 (16)
C9	0.0331 (16)	0.0435 (19)	0.0334 (16)	0.0037 (14)	−0.0015 (13)	0.0015 (13)
C10	0.0389 (18)	0.0436 (19)	0.0354 (16)	0.0040 (15)	0.0006 (13)	−0.0007 (14)
C3	0.050 (2)	0.049 (2)	0.0398 (18)	0.0120 (16)	0.0042 (15)	−0.0070 (15)
C13	0.071 (3)	0.083 (3)	0.045 (2)	0.020 (2)	−0.0027 (19)	−0.022 (2)
C11	0.046 (2)	0.046 (2)	0.0379 (17)	0.0096 (16)	−0.0007 (15)	0.0021 (14)
C4	0.048 (2)	0.054 (2)	0.051 (2)	0.0195 (17)	0.0041 (16)	−0.0053 (16)
C12	0.062 (3)	0.069 (3)	0.040 (2)	0.009 (2)	−0.0111 (17)	−0.0053 (18)
C6	0.0348 (17)	0.0389 (18)	0.0440 (18)	0.0088 (14)	0.0004 (13)	−0.0017 (14)
C14	0.063 (3)	0.076 (3)	0.056 (2)	0.024 (2)	0.0040 (19)	−0.019 (2)
O5	0.0379 (13)	0.0562 (15)	0.0488 (13)	0.0164 (11)	−0.0074 (10)	−0.0079 (11)
N3	0.0310 (14)	0.0506 (18)	0.0537 (17)	0.0044 (12)	−0.0062 (12)	−0.0006 (13)
C17	0.0346 (18)	0.049 (2)	0.050 (2)	0.0069 (15)	−0.0017 (15)	0.0024 (16)
C16	0.047 (2)	0.070 (3)	0.060 (2)	0.0083 (19)	−0.0155 (18)	−0.0032 (19)
C1	0.061 (3)	0.077 (3)	0.055 (2)	0.010 (2)	−0.014 (2)	−0.022 (2)
C18	0.045 (2)	0.076 (3)	0.077 (3)	0.026 (2)	−0.003 (2)	−0.005 (2)

Geometric parameters (Å, º) top

Cu1—O2	1.874 (2)	C9—C10	1.470 (4)
Cu1—N1	1.907 (3)	C10—C11	1.399 (4)
Cu1—O3	1.936 (2)	C3—C4	1.398 (5)
Cu1—O5	1.948 (2)	C3—H3A	0.9300
Br1—C4	1.899 (4)	C13—C14	1.364 (6)
O2—C7	1.294 (4)	C13—C12	1.365 (6)
O3—C9	1.282 (4)	C13—H13A	0.9300
N1—C8	1.281 (4)	C11—C12	1.385 (5)
N1—N2	1.386 (3)	C12—H12A	0.9300
C8—C6	1.429 (4)	C14—H14A	0.9300
C8—H8A	0.9300	O5—C17	1.262 (4)
N2—C9	1.326 (4)	N3—C17	1.284 (4)
O4—C11	1.359 (4)	N3—C18	1.446 (5)
O4—H4A	0.8200	N3—C16	1.454 (5)
O1—C2	1.369 (4)	C17—H17A	0.9300
O1—C1	1.414 (4)	C16—H16A	0.9600
C7—C6	1.418 (4)	C16—H16B	0.9600
C7—C2	1.426 (4)	C16—H16C	0.9600
C5—C4	1.345 (5)	C1—H1A	0.9600
C5—C6	1.412 (5)	C1—H1B	0.9600
C5—H5A	0.9300	C1—H1C	0.9600
C2—C3	1.358 (5)	C18—H18A	0.9600
C15—C14	1.367 (5)	C18—H18B	0.9600
C15—C10	1.382 (5)	C18—H18C	0.9600
C15—H15A	0.9300

O2—Cu1—N1	93.33 (10)	O4—C11—C12	117.5 (3)
O2—Cu1—O3	174.87 (9)	O4—C11—C10	122.6 (3)
N1—Cu1—O3	81.62 (10)	C12—C11—C10	119.8 (3)
O2—Cu1—O5	91.67 (10)	C5—C4—C3	122.0 (3)
N1—Cu1—O5	172.69 (11)	C5—C4—Br1	119.4 (3)
O3—Cu1—O5	93.28 (9)	C3—C4—Br1	118.7 (3)
C7—O2—Cu1	127.5 (2)	C13—C12—C11	120.0 (4)
C9—O3—Cu1	110.17 (19)	C13—C12—H12A	120.0
C8—N1—N2	118.0 (3)	C11—C12—H12A	120.0
C8—N1—Cu1	127.4 (2)	C5—C6—C7	119.7 (3)
N2—N1—Cu1	114.56 (19)	C5—C6—C8	117.7 (3)
N1—C8—C6	124.1 (3)	C7—C6—C8	122.6 (3)
N1—C8—H8A	118.0	C13—C14—C15	119.5 (4)
C6—C8—H8A	118.0	C13—C14—H14A	120.2
C9—N2—N1	109.4 (2)	C15—C14—H14A	120.2
C11—O4—H4A	109.5	C17—O5—Cu1	122.1 (2)
C2—O1—C1	118.4 (3)	C17—N3—C18	121.9 (3)
O2—C7—C6	124.4 (3)	C17—N3—C16	121.1 (3)
O2—C7—C2	118.6 (3)	C18—N3—C16	117.0 (3)
C6—C7—C2	117.0 (3)	O5—C17—N3	123.4 (3)
C4—C5—C6	120.2 (3)	O5—C17—H17A	118.3
C4—C5—H5A	119.9	N3—C17—H17A	118.3
C6—C5—H5A	119.9	N3—C16—H16A	109.5
C3—C2—O1	124.7 (3)	N3—C16—H16B	109.5
C3—C2—C7	122.2 (3)	H16A—C16—H16B	109.5
O1—C2—C7	113.1 (3)	N3—C16—H16C	109.5
C14—C15—C10	121.6 (3)	H16A—C16—H16C	109.5
C14—C15—H15A	119.2	H16B—C16—H16C	109.5
C10—C15—H15A	119.2	O1—C1—H1A	109.5
O3—C9—N2	123.8 (3)	O1—C1—H1B	109.5
O3—C9—C10	119.6 (3)	H1A—C1—H1B	109.5
N2—C9—C10	116.5 (3)	O1—C1—H1C	109.5
C15—C10—C11	118.0 (3)	H1A—C1—H1C	109.5
C15—C10—C9	119.2 (3)	H1B—C1—H1C	109.5
C11—C10—C9	122.8 (3)	N3—C18—H18A	109.5
C2—C3—C4	118.9 (3)	N3—C18—H18B	109.5
C2—C3—H3A	120.6	H18A—C18—H18B	109.5
C4—C3—H3A	120.6	N3—C18—H18C	109.5
C14—C13—C12	120.9 (4)	H18A—C18—H18C	109.5
C14—C13—H13A	119.6	H18B—C18—H18C	109.5
C12—C13—H13A	119.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···N2	0.82	1.84	2.566 (3)	146

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₅H₁₁BrN₂O₄)₂(C₃H₇NO)₂]
M_r	999.61
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.3861 (17), 9.5795 (19), 12.275 (3)
α, β, γ (°)	90.446 (3), 97.850 (3), 101.688 (3)
V (Å³)	956.0 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	3.27
Crystal size (mm)	0.38 × 0.25 × 0.16

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.371, 0.620
No. of measured, independent and observed [I > 2σ(I)] reflections	5880, 4354, 2957
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.694

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.123, 0.99
No. of reflections	4354
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.58

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···N2	0.82	1.84	2.566 (3)	146.4

Acknowledgements

This project was supported by the National Natural Science Foundation of China (program Nos. 21103135 and 21073139), the Natural Science Basic Research Plan in Shaanxi Province of China (program No. 2011JQ2011), the Foundation of Xi'an University of Science and Technology (program No. 2010QDJ030), the Scientific Research Program funded by Shaanxi Provincial Education Department (program No.12 J K0622) and the Open Foundation of the Laboratory of Space Materials Science and Technology of NWPU.

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Huang, S.-M., Jiang, F.-F., Chen, X.-H. & Wu, Q.-J. (2010). Acta Cryst. E66, m456. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, S., Li, L., Liu, X., Feng, W. & Lü, X. (2012). Acta Cryst. E68, o2040. CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 9| September 2012| Page m1216

doi:10.1107/S1600536812036100

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis[μ-N′-(5-bromo-3-meth­­oxy-2-oxido­benzyl­­idene)-2-hydroxybenzohydra­zidato]bis­[(N,N-di­methyl­formamide)­copper(II)]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[μ-N′-(5-bromo-3-methoxy-2-oxidobenzylidene)-2-hydroxybenzohydrazidato]bis[(N,N-dimethylformamide)copper(II)]