Bis[2,4-di­bromo-6-(N-{4-[(E)-1-(benzyl­oxy­imino)­eth­yl]phen­yl}carboximido­yl)phenolato]copper(II)

Li, X.-B.; Li, X.-J.; Meng, W.-S.; Zhang, Y.-J.; Li, G.

doi:10.1107/S1600536813009847

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page m267

https://doi.org/10.1107/S1600536813009847

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Bis[2,4-dibromo-6-(N-{4-[(E)-1-(benzyloxyimino)ethyl]phenyl}carboximidoyl)phenolato]copper(II)

Xiao-Bing Li,^a,^b ^* Xiao-Jun Li,^c Wei-Sheng Meng,^d Yu-Jie Zhang ^d and Gang Li ^d

^aInformation Centre, Gansu Institute of Forestry Survey and Planning, Lanzhou 730020, People's Republic of China, ^bCollege of Earth and Environmental Scieces, Lanzhou University, Lanzhou 730000, People's Republic of China, ^cZhaosheng Office of Gansu Province, Lanzhou 730030, People's Republic of China, and ^dSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: li_gang78@126.com

(Received 7 April 2013; accepted 10 April 2013; online 13 April 2013)

In the title complex, [Cu(C₂₂H₁₇Br₂N₂O₂)₂], the Cu^II ion is four-coordinated in a trans-CuN₂O₂ square-planar geometry by two phenolate O and two imino N atoms from two deprotonated N,O-bidentate ligands. In the crystal, the packing of the molecules is controlled by C—H⋯π and π–π interactions [centroid–centroid distances = 3.568 (3), 3.678 (2), 3.717 (3) and 3.799 (2) Å] and weak Br⋯Br halogen bonds [3.508 (4) Å], linking the molecules into an infinite three-dimensional supramolecular network.

Related literature

For background to oxime-based salen-type tetradentate ligands, see: Akine et al. (2001 ); Dong & Ding (2007 ); Dong et al. (2012 ); Bertolasi et al. (1982 ); Tarafder et al. (2002 ). For the synthesis and related crystal structures, see: Zhao & Ng (2010 ); Zhao et al. (2012 ); Dong et al. (2010 ).

Experimental

Crystal data

[Cu(C₂₂H₁₇Br₂N₂O₂)₂]
M_r = 1065.93
Monoclinic, C 2/c
a = 27.4484 (7) Å
b = 13.3116 (3) Å
c = 22.3609 (5) Å
β = 91.165 (2)°
V = 8168.6 (3) Å³
Z = 8
Mo Kα radiation
μ = 4.50 mm⁻¹
T = 293 K
0.30 × 0.21 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.346, T_max = 0.662
27775 measured reflections
7199 independent reflections
4682 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.078
S = 1.01
7199 reflections
514 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the Cu/O4/C33–C31/N4 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯Cg1ⁱ	0.93	2.82	3.575 (5)	118
C16—H16B⋯Cg2ⁱ	0.97	2.96	3.511 (5)	117
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813009847/zl2543sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813009847/zl2543Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813009847/zl2543Isup3.tif

checkCIF report

Comment top

Cu^II complexes with Schiff base ligands have been widely investigated in coordination chemistry and biological chemistry (Akine et al., 2001; Dong et al., 2012). In the last few years there has been a burgeoning effort to identify the biological activities of Cu^II ions, primarily through techniques associated with the interface of biology/biochemistry/coordination chemistry (Dong et al., 2007; Tarafder et al., 2002). The oxime moiety can both donate and accept hydrogen bonds, which makes it a very interesting building block in supramolecular chemistry (Bertolasi et al., 1982). Herein a new double functional group ligand bearing both a Schiff base and an oxime group, 2,4-dibromo-6-(N-{4-[(E)-1-(phenoxyimino)ethyl]phenyl}carboximidoyl)phenol and its Cu^II complex, [Cu(C₂₂H₁₇Br₂N₂O₂)₂], are reported.

The structure of the title complex is shown in Fig. 1. In the title complex, all bond lengths and angles are in normal ranges. The molecule has approximate chemical inversion symmetry, but no crystallographic inversion symmetry. The Cu^II ion is four-coordinated in a trans-CuN₂O₂ square-planar geometry, with two phenolate O and two imino N atoms from two deprotonated N,O-bidentate ligands (Dong et al., 2010). The copper atom of [Cu(C₂₂H₁₇Br₂N₂O₂)₂] has a square planar geometry distorted tetrahedrally by 13.91 (5)° (defined by the angle between two sets of N—Cu—O planes). A similar distortion has also been observed for the ethoxyl analogue of the title complex (23.33 (3)°) (Zhao et al., 2012).

In the crystal structure, the molecules are linked into an infinite supramolecular network by two C—H···π interactions, C19—H19···Cg1 (N4/Cu1/O4/C31—C33) and C16—H16B···Cg2 (C10—C15), and four intermolecular π···π stacking interactions, Cg2ⁱ···Cg3 (Cu1/O2/N2/C9—C11) [3.799 (2) Å], Cg3···Cg4ⁱⁱ (C17—C22) [3.568 (3)Å], Cg2···Cg2ⁱ [3.678 (2) Å] and Cg5 (C32—C37)···Cg5ⁱⁱⁱ [3.717 (3) Å] [symmetry codes: (i) 1/2 - x,3/2 - y,1 - z, (ii) x, 1-y, -1/2+z, (iii) 1-x, y, 3/2-z] (Fig. 2). In addition, the crystal packing is further stabilized by weak intermolecular Br···Br halogen bonds with a distance of 3.508 (4) Å.

Related literature top

For background to oxime-based salen-type tetradentate ligands, see: Akine et al. (2001); Dong & Ding (2007); Dong et al. (2012); Bertolasi et al. (1982); Tarafder et al. (2002). For the synthesis and related crystal structures, see: Zhao & Ng (2010); Zhao et al. (2012); Dong et al. (2010).

Experimental top

1-(4-{[(E)-3,5-dibromo-2-hydroxybenzylidene]amino}phenyl)ethanone O-benzyloxime was synthesized by reaction of O-benzylhydroxylamine, 4-aminoacetophenone and 3,5-dibromosalicylaldehyde (Zhao et al., 2010).

To an ethanol solution (6 ml) of O-benzylhydroxylamine (340.9 mg, 3 mmol) was added an ethanol solution (12 ml) of 4-aminoacetophenone (349.5 mg, 3 mmol) and 3 drops of acetic acid. The reaction solution was stirred at 338 K for 24 h. The solvent was evaporated under vacuo. After cooling to room temperature, the formed precipitate was filtered off and washed successively with ethanol and ethanol/water (1:4), respectively, resulting in 640.6 mg of ({4-amino}phenyl)ethanone O-benzyloxime as a crystalline solid. Yield, 92.8%, m.p. 348–350 K. Anal. Calcd. for C₁₅H₁₆N_2O (%): C, 74.97; H, 6.71; N, 11.66. Found: C, 74.68; H, 6.80; N, 11.52.

To an ethanol solution (4 ml) of ({4-amino}phenyl)ethanone O-benzyloxime (213.2 mg, 0.89 mmol) was added an ethanol solution (2 ml) of 3,5-dibromosalicylaldehyde (2 49.3 mg, 0.89 mmol). The reaction solution was stirred at 333 K for 18 h. After cooling to room temperature, the formed precipitate was filtered off and washed successively with ethanol and ethanol/n-hexane (1:4), respectively. The product was dried in vacuo and purified by recrystallization from ethanol to yield 273.3 mg of 1-(4-{[(E)-3,5-dibromo-2-hydroxybenzylidene]amino}phenyl)ethanone O-benzyloxime. Yield, 59.1%. m.p. 441–442 K. IR: ν C=N, 1608 cm^-1 and ν Ar—O, 1198 cm^-1. Anal. Calcd. for C₂₂H₁₈Br₂N₂O₂ (%): C, 52.62; H, 3.61; N, 5.58. Found: C, 52.49; H, 3.57, N, 5.53.

A pale-blue methanol solution (3 ml) of Cu^II acetate monohydrate (0.5 mg, 0.001 mmol) was added dropwise to a red ethyl acetate solution (3 ml) of 1-(4-{[(E)-3,5-dibromo-2-hydroxybenzylidene]amino}phenyl)ethanone O-benzyloxime (2.6 mg, 0.002 mmol) at room temperature. Upon mixing, the color of the solution turned slowly to brown and the solution was allowed to stand at room temperature for about one week. The solvent was partially evaporated and brown block-like single crystals suitable for X-ray crystallographic analysis were obtained. IR: ν C=N, 1605 cm^-1 and ν Ar—O, 1186 cm^-1. Anal. Calcd. for [Cu(C₂₂H₁₇Br₂N₂O₂)₂] (C₄₄H₃₄Br₄CuN₄O₄) (%): C, 49.58; H, 3.22; N, 5.26; Cu, 5.96. Found: C, 49.75; H, 3.13; N, 5.06; Cu, 5.72.

Structure description top

For background to oxime-based salen-type tetradentate ligands, see: Akine et al. (2001); Dong & Ding (2007); Dong et al. (2012); Bertolasi et al. (1982); Tarafder et al. (2002). For the synthesis and related crystal structures, see: Zhao & Ng (2010); Zhao et al. (2012); Dong et al. (2010).

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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex with the atom numbering scheme, showing 30% probability displacement ellipsoids. All the H atoms on carbon have been omitted for clarity.
	Fig. 2. View of the C—H···π and π···π interactions of the title complex (hydrogen atoms, except those forming hydrogen bonds, are omitted for clarity).
	Fig. 3. Synthetic route to 1-(4-{[(E)-3,5-dibromo-2-hydroxybenzylidene]amino} phenyl)ethanone O-benzyloxime

Bis[2,4-dibromo-6-(N-{4-[(E)-1-(benzyloxyimino)ethyl]phenyl}carboximidoyl)phenolato]copper(II) top

Crystal data top

[Cu(C₂₂H₁₇Br₂N₂O₂)₂]	F(000) = 4216
M_r = 1065.93	D_x = 1.733 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5329 reflections
a = 27.4484 (7) Å	θ = 2.5–28.4°
b = 13.3116 (3) Å	µ = 4.50 mm⁻¹
c = 22.3609 (5) Å	T = 293 K
β = 91.165 (2)°	Block-like, brown
V = 8168.6 (3) Å³	0.30 × 0.21 × 0.10 mm
Z = 8

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	7199 independent reflections
Radiation source: fine-focus sealed tube	4682 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
phi and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −32→32
T_min = 0.346, T_max = 0.662	k = −15→15
27775 measured reflections	l = −26→26

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0217P)² + 4.428P] where P = (F_o² + 2F_c²)/3
7199 reflections	(Δ/σ)_max = 0.001
514 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Cu(C₂₂H₁₇Br₂N₂O₂)₂]	V = 8168.6 (3) Å³
M_r = 1065.93	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 27.4484 (7) Å	µ = 4.50 mm⁻¹
b = 13.3116 (3) Å	T = 293 K
c = 22.3609 (5) Å	0.30 × 0.21 × 0.10 mm
β = 91.165 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	7199 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4682 reflections with I > 2σ(I)
T_min = 0.346, T_max = 0.662	R_int = 0.063
27775 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.01	Δρ_max = 0.38 e Å⁻³
7199 reflections	Δρ_min = −0.36 e Å⁻³
514 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	0.393085 (19)	0.80478 (4)	0.56844 (2)	0.03676 (15)
Br1	0.313417 (19)	1.00341 (3)	0.41540 (2)	0.05451 (16)
Br2	0.202079 (18)	0.66785 (3)	0.34341 (2)	0.04794 (14)
Br3	0.51425 (2)	0.59414 (4)	0.66431 (3)	0.07055 (19)
Br4	0.61488 (2)	0.93975 (4)	0.74609 (3)	0.0720 (2)
N1	0.40018 (14)	0.3244 (3)	0.75569 (17)	0.0462 (10)
N2	0.36392 (12)	0.6673 (2)	0.56013 (14)	0.0334 (9)
N3	0.34560 (16)	1.3351 (3)	0.44525 (19)	0.0558 (12)
N4	0.41632 (12)	0.9450 (2)	0.58442 (15)	0.0369 (9)
O1	0.41180 (12)	0.2328 (2)	0.78465 (14)	0.0582 (9)
O2	0.35153 (10)	0.85865 (18)	0.50786 (12)	0.0377 (7)
O3	0.32379 (14)	1.4261 (2)	0.42526 (16)	0.0681 (11)
O4	0.44441 (10)	0.74996 (19)	0.61628 (12)	0.0427 (8)
C1	0.4484 (2)	0.2458 (4)	0.6779 (2)	0.0712 (17)
H1A	0.4798	0.2719	0.6680	0.107*
H1B	0.4326	0.2197	0.6425	0.107*
H1C	0.4523	0.1929	0.7068	0.107*
C2	0.41821 (17)	0.3274 (3)	0.7033 (2)	0.0403 (11)
C3	0.40625 (15)	0.4177 (3)	0.66696 (19)	0.0356 (11)
C4	0.38720 (17)	0.5041 (3)	0.69259 (19)	0.0466 (12)
H4	0.3828	0.5063	0.7337	0.056*
C5	0.37466 (17)	0.5867 (3)	0.6582 (2)	0.0457 (12)
H5	0.3629	0.6444	0.6765	0.055*
C6	0.37943 (15)	0.5841 (3)	0.59716 (19)	0.0352 (11)
C7	0.39876 (15)	0.4995 (3)	0.57136 (19)	0.0406 (11)
H7	0.4030	0.4976	0.5302	0.049*
C8	0.41192 (16)	0.4171 (3)	0.60602 (19)	0.0390 (11)
H8	0.4248	0.3605	0.5877	0.047*
C9	0.33200 (15)	0.6446 (3)	0.51906 (17)	0.0354 (11)
H9	0.3225	0.5776	0.5175	0.042*
C10	0.30944 (15)	0.7097 (3)	0.47563 (17)	0.0312 (10)
C11	0.32100 (15)	0.8134 (3)	0.47231 (18)	0.0331 (10)
C12	0.29653 (15)	0.8671 (3)	0.42596 (18)	0.0325 (10)
C13	0.26243 (15)	0.8249 (3)	0.38851 (18)	0.0363 (11)
H13	0.2468	0.8636	0.3593	0.044*
C14	0.25130 (15)	0.7241 (3)	0.39428 (18)	0.0360 (11)
C15	0.27448 (15)	0.6672 (3)	0.43670 (18)	0.0372 (11)
H15	0.2670	0.5992	0.4399	0.045*
C16	0.38905 (19)	0.2287 (4)	0.8420 (2)	0.0617 (15)
H16A	0.3783	0.1605	0.8494	0.074*
H16B	0.3605	0.2717	0.8413	0.074*
C17	0.42285 (17)	0.2612 (4)	0.8916 (2)	0.0478 (13)
C18	0.44426 (19)	0.1915 (4)	0.9290 (2)	0.0588 (14)
H18	0.4375	0.1237	0.9235	0.071*
C19	0.4758 (2)	0.2208 (5)	0.9748 (2)	0.0738 (17)
H19	0.4898	0.1729	1.0000	0.089*
C20	0.4861 (2)	0.3197 (6)	0.9829 (3)	0.0772 (18)
H20	0.5074	0.3395	1.0135	0.093*
C21	0.4656 (2)	0.3894 (5)	0.9463 (3)	0.0780 (18)
H21	0.4727	0.4571	0.9519	0.094*
C22	0.4340 (2)	0.3602 (4)	0.9009 (2)	0.0674 (16)
H22	0.4199	0.4087	0.8761	0.081*
C23	0.28957 (18)	1.3574 (3)	0.5297 (2)	0.0584 (14)
H23A	0.3038	1.3891	0.5644	0.088*
H23B	0.2659	1.3089	0.5419	0.088*
H23C	0.2740	1.4073	0.5049	0.088*
C24	0.32845 (18)	1.3061 (3)	0.4953 (2)	0.0445 (12)
C25	0.35100 (17)	1.2114 (3)	0.5185 (2)	0.0408 (12)
C26	0.33122 (18)	1.1602 (3)	0.5662 (2)	0.0509 (13)
H26	0.3039	1.1860	0.5848	0.061*
C27	0.35166 (17)	1.0705 (3)	0.5865 (2)	0.0494 (13)
H27	0.3378	1.0361	0.6181	0.059*
C28	0.39222 (16)	1.0333 (3)	0.5599 (2)	0.0364 (11)
C29	0.41171 (17)	1.0817 (3)	0.5122 (2)	0.0496 (13)
H29	0.4387	1.0548	0.4935	0.060*
C30	0.39136 (18)	1.1708 (3)	0.4915 (2)	0.0502 (13)
H30	0.4050	1.2036	0.4592	0.060*
C31	0.45492 (16)	0.9665 (3)	0.61517 (19)	0.0432 (12)
H31	0.4622	1.0344	0.6191	0.052*
C32	0.48802 (16)	0.8982 (3)	0.64407 (19)	0.0412 (12)
C33	0.48142 (17)	0.7931 (3)	0.64184 (18)	0.0398 (11)
C34	0.51902 (17)	0.7353 (3)	0.66960 (19)	0.0432 (12)
C35	0.55761 (17)	0.7769 (3)	0.70001 (19)	0.0468 (13)
H35	0.5808	0.7359	0.7186	0.056*
C36	0.56205 (17)	0.8805 (3)	0.7030 (2)	0.0482 (13)
C37	0.52853 (17)	0.9402 (3)	0.6752 (2)	0.0504 (13)
H37	0.5323	1.0096	0.6765	0.060*
C38	0.3297 (2)	1.4292 (4)	0.3611 (2)	0.0734 (17)
H38A	0.3619	1.4047	0.3515	0.088*
H38B	0.3271	1.4982	0.3474	0.088*
C39	0.2922 (2)	1.3669 (4)	0.3295 (2)	0.0670 (16)
C40	0.2531 (3)	1.4106 (5)	0.2979 (3)	0.094 (2)
H40	0.2512	1.4800	0.2937	0.112*
C41	0.2170 (3)	1.3490 (7)	0.2726 (3)	0.099 (2)
H41	0.1913	1.3782	0.2512	0.119*
C42	0.2187 (3)	1.2477 (7)	0.2784 (3)	0.100 (2)
H42	0.1936	1.2082	0.2625	0.120*
C43	0.2571 (3)	1.2046 (5)	0.3074 (2)	0.088 (2)
H43	0.2589	1.1350	0.3104	0.106*
C44	0.2934 (2)	1.2630 (4)	0.3324 (2)	0.0703 (17)
H44	0.3196	1.2319	0.3518	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0360 (3)	0.0314 (3)	0.0423 (3)	0.0009 (2)	−0.0114 (3)	0.0010 (2)
Br1	0.0655 (4)	0.0335 (2)	0.0637 (3)	−0.0007 (2)	−0.0166 (3)	0.0084 (2)
Br2	0.0466 (3)	0.0513 (3)	0.0453 (3)	−0.0020 (2)	−0.0140 (2)	−0.0079 (2)
Br3	0.0702 (4)	0.0431 (3)	0.0970 (4)	0.0108 (3)	−0.0295 (4)	0.0048 (3)
Br4	0.0546 (4)	0.0807 (4)	0.0791 (4)	−0.0073 (3)	−0.0361 (3)	−0.0002 (3)
N1	0.048 (3)	0.042 (2)	0.049 (3)	0.0007 (19)	−0.001 (2)	0.015 (2)
N2	0.036 (2)	0.0293 (18)	0.035 (2)	0.0047 (17)	−0.0067 (19)	0.0026 (16)
N3	0.069 (3)	0.037 (2)	0.061 (3)	0.010 (2)	−0.012 (3)	0.007 (2)
N4	0.034 (2)	0.0289 (19)	0.047 (2)	0.0040 (17)	−0.013 (2)	−0.0001 (17)
O1	0.067 (2)	0.055 (2)	0.053 (2)	0.0056 (18)	0.0068 (19)	0.0220 (17)
O2	0.0375 (18)	0.0325 (15)	0.0427 (18)	−0.0023 (14)	−0.0125 (16)	0.0009 (14)
O3	0.095 (3)	0.043 (2)	0.065 (2)	0.018 (2)	−0.006 (2)	0.0105 (18)
O4	0.044 (2)	0.0315 (16)	0.0516 (19)	0.0005 (14)	−0.0208 (17)	0.0043 (14)
C1	0.085 (4)	0.065 (4)	0.063 (4)	0.029 (3)	0.012 (3)	0.016 (3)
C2	0.040 (3)	0.039 (3)	0.042 (3)	0.005 (2)	−0.003 (2)	0.008 (2)
C3	0.035 (3)	0.035 (2)	0.037 (3)	0.000 (2)	0.001 (2)	0.002 (2)
C4	0.061 (3)	0.048 (3)	0.031 (3)	0.006 (3)	0.002 (2)	0.005 (2)
C5	0.057 (3)	0.038 (3)	0.042 (3)	0.008 (2)	0.000 (3)	−0.002 (2)
C6	0.035 (3)	0.031 (2)	0.039 (3)	0.002 (2)	−0.010 (2)	0.003 (2)
C7	0.046 (3)	0.045 (3)	0.031 (3)	0.002 (2)	0.001 (2)	0.003 (2)
C8	0.042 (3)	0.035 (2)	0.039 (3)	0.004 (2)	0.001 (2)	0.001 (2)
C9	0.037 (3)	0.033 (2)	0.036 (3)	−0.002 (2)	−0.003 (2)	−0.003 (2)
C10	0.029 (3)	0.034 (2)	0.030 (2)	0.002 (2)	0.000 (2)	0.001 (2)
C11	0.031 (3)	0.034 (2)	0.034 (3)	0.004 (2)	0.001 (2)	−0.002 (2)
C12	0.030 (3)	0.033 (2)	0.034 (2)	0.004 (2)	0.001 (2)	0.002 (2)
C13	0.038 (3)	0.040 (3)	0.031 (2)	0.007 (2)	−0.002 (2)	0.002 (2)
C14	0.034 (3)	0.043 (3)	0.031 (2)	0.001 (2)	−0.005 (2)	−0.007 (2)
C15	0.039 (3)	0.034 (2)	0.038 (3)	−0.004 (2)	−0.001 (2)	0.001 (2)
C16	0.055 (4)	0.073 (4)	0.057 (3)	−0.007 (3)	0.007 (3)	0.028 (3)
C17	0.039 (3)	0.058 (3)	0.047 (3)	0.000 (3)	0.012 (3)	0.012 (3)
C18	0.060 (4)	0.062 (3)	0.055 (3)	0.009 (3)	0.012 (3)	0.013 (3)
C19	0.065 (4)	0.100 (5)	0.058 (4)	0.014 (4)	0.007 (3)	0.020 (4)
C20	0.060 (4)	0.115 (6)	0.057 (4)	−0.015 (4)	0.009 (3)	−0.001 (4)
C21	0.082 (5)	0.077 (4)	0.076 (4)	−0.013 (4)	0.020 (4)	−0.006 (4)
C22	0.065 (4)	0.067 (4)	0.070 (4)	0.004 (3)	0.011 (3)	0.017 (3)
C23	0.055 (3)	0.042 (3)	0.078 (4)	0.006 (3)	−0.006 (3)	0.007 (3)
C24	0.045 (3)	0.033 (3)	0.055 (3)	0.001 (2)	−0.009 (3)	−0.002 (2)
C25	0.040 (3)	0.030 (2)	0.051 (3)	−0.003 (2)	−0.010 (3)	0.001 (2)
C26	0.047 (3)	0.047 (3)	0.058 (3)	0.015 (3)	0.001 (3)	0.007 (3)
C27	0.050 (3)	0.043 (3)	0.056 (3)	0.009 (3)	0.004 (3)	0.009 (2)
C28	0.033 (3)	0.029 (2)	0.048 (3)	−0.003 (2)	−0.010 (2)	0.000 (2)
C29	0.040 (3)	0.044 (3)	0.065 (3)	0.008 (2)	0.004 (3)	0.006 (3)
C30	0.051 (3)	0.043 (3)	0.057 (3)	0.002 (3)	0.003 (3)	0.012 (2)
C31	0.043 (3)	0.034 (2)	0.052 (3)	0.002 (2)	−0.008 (3)	−0.002 (2)
C32	0.040 (3)	0.036 (3)	0.047 (3)	0.002 (2)	−0.013 (2)	0.003 (2)
C33	0.039 (3)	0.044 (3)	0.036 (3)	0.005 (2)	−0.004 (2)	0.000 (2)
C34	0.044 (3)	0.042 (3)	0.043 (3)	0.006 (2)	−0.007 (3)	0.002 (2)
C35	0.041 (3)	0.054 (3)	0.045 (3)	0.007 (3)	−0.010 (3)	0.006 (2)
C36	0.040 (3)	0.056 (3)	0.049 (3)	0.000 (2)	−0.018 (3)	0.001 (2)
C37	0.049 (3)	0.043 (3)	0.058 (3)	−0.003 (2)	−0.016 (3)	−0.004 (2)
C38	0.098 (5)	0.059 (4)	0.063 (4)	0.017 (3)	0.012 (4)	0.020 (3)
C39	0.077 (5)	0.078 (4)	0.046 (3)	0.030 (4)	0.003 (3)	0.007 (3)
C40	0.111 (6)	0.103 (5)	0.067 (4)	0.053 (5)	0.002 (4)	−0.005 (4)
C41	0.085 (6)	0.144 (7)	0.069 (5)	0.057 (5)	−0.013 (4)	−0.006 (5)
C42	0.079 (5)	0.150 (7)	0.071 (5)	0.015 (5)	−0.003 (4)	−0.008 (5)
C43	0.096 (5)	0.108 (5)	0.061 (4)	0.003 (5)	−0.012 (4)	0.003 (4)
C44	0.073 (4)	0.081 (4)	0.056 (4)	0.010 (4)	−0.011 (3)	0.003 (3)

Geometric parameters (Å, º) top

Cu1—O2	1.894 (2)	C17—C18	1.373 (6)
Cu1—O4	1.897 (3)	C18—C19	1.382 (7)
Cu1—N4	2.002 (3)	C18—H18	0.9300
Cu1—N2	2.005 (3)	C19—C20	1.358 (7)
Br1—C12	1.888 (4)	C19—H19	0.9300
Br2—C14	1.902 (4)	C20—C21	1.352 (7)
Br3—C34	1.887 (4)	C20—H20	0.9300
Br4—C36	1.896 (4)	C21—C22	1.377 (7)
N1—C2	1.282 (5)	C21—H21	0.9300
N1—O1	1.413 (4)	C22—H22	0.9300
N2—C9	1.292 (4)	C23—C24	1.494 (6)
N2—C6	1.442 (5)	C23—H23A	0.9600
N3—C24	1.283 (6)	C23—H23B	0.9600
N3—O3	1.420 (4)	C23—H23C	0.9600
N4—C31	1.284 (5)	C24—C25	1.492 (6)
N4—C28	1.451 (5)	C25—C30	1.383 (6)
O1—C16	1.438 (5)	C25—C26	1.385 (6)
O2—C11	1.292 (4)	C26—C27	1.392 (5)
O3—C38	1.447 (6)	C26—H26	0.9300
O4—C33	1.290 (5)	C27—C28	1.366 (6)
C1—C2	1.487 (6)	C27—H27	0.9300
C1—H1A	0.9600	C28—C29	1.364 (6)
C1—H1B	0.9600	C29—C30	1.387 (6)
C1—H1C	0.9600	C29—H29	0.9300
C2—C3	1.483 (5)	C30—H30	0.9300
C3—C8	1.375 (5)	C31—C32	1.430 (5)
C3—C4	1.393 (5)	C31—H31	0.9300
C4—C5	1.381 (5)	C32—C33	1.411 (5)
C4—H4	0.9300	C32—C37	1.415 (5)
C5—C6	1.375 (6)	C33—C34	1.420 (5)
C5—H5	0.9300	C34—C35	1.364 (6)
C6—C7	1.377 (5)	C35—C36	1.386 (6)
C7—C8	1.387 (5)	C35—H35	0.9300
C7—H7	0.9300	C36—C37	1.357 (6)
C8—H8	0.9300	C37—H37	0.9300
C9—C10	1.433 (5)	C38—C39	1.490 (7)
C9—H9	0.9300	C38—H38A	0.9700
C10—C15	1.402 (5)	C38—H38B	0.9700
C10—C11	1.419 (5)	C39—C44	1.385 (7)
C11—C12	1.417 (5)	C39—C40	1.398 (7)
C12—C13	1.365 (5)	C40—C41	1.396 (9)
C13—C14	1.382 (5)	C40—H40	0.9300
C13—H13	0.9300	C41—C42	1.355 (9)
C14—C15	1.362 (5)	C41—H41	0.9300
C15—H15	0.9300	C42—C43	1.354 (8)
C16—C17	1.496 (6)	C42—H42	0.9300
C16—H16A	0.9700	C43—C44	1.375 (7)
C16—H16B	0.9700	C43—H43	0.9300
C17—C22	1.368 (6)	C44—H44	0.9300

O2—Cu1—O4	168.03 (13)	C21—C20—C19	120.0 (6)
O2—Cu1—N4	87.69 (12)	C21—C20—H20	120.0
O4—Cu1—N4	91.59 (12)	C19—C20—H20	120.0
O2—Cu1—N2	92.63 (12)	C20—C21—C22	120.0 (6)
O4—Cu1—N2	89.52 (12)	C20—C21—H21	120.0
N4—Cu1—N2	173.08 (15)	C22—C21—H21	120.0
C2—N1—O1	111.0 (4)	C17—C22—C21	121.3 (5)
C9—N2—C6	114.6 (3)	C17—C22—H22	119.3
C9—N2—Cu1	122.9 (3)	C21—C22—H22	119.3
C6—N2—Cu1	122.4 (2)	C24—C23—H23A	109.5
C24—N3—O3	111.8 (4)	C24—C23—H23B	109.5
C31—N4—C28	112.7 (3)	H23A—C23—H23B	109.5
C31—N4—Cu1	124.0 (3)	C24—C23—H23C	109.5
C28—N4—Cu1	123.2 (2)	H23A—C23—H23C	109.5
N1—O1—C16	110.1 (3)	H23B—C23—H23C	109.5
C11—O2—Cu1	129.6 (2)	N3—C24—C25	113.6 (5)
N3—O3—C38	106.3 (4)	N3—C24—C23	126.2 (4)
C33—O4—Cu1	130.3 (3)	C25—C24—C23	120.2 (4)
C2—C1—H1A	109.5	C30—C25—C26	118.3 (4)
C2—C1—H1B	109.5	C30—C25—C24	120.6 (4)
H1A—C1—H1B	109.5	C26—C25—C24	121.1 (5)
C2—C1—H1C	109.5	C25—C26—C27	120.8 (5)
H1A—C1—H1C	109.5	C25—C26—H26	119.6
H1B—C1—H1C	109.5	C27—C26—H26	119.6
N1—C2—C3	116.2 (4)	C28—C27—C26	119.7 (5)
N1—C2—C1	123.7 (4)	C28—C27—H27	120.2
C3—C2—C1	120.1 (4)	C26—C27—H27	120.2
C8—C3—C4	117.6 (4)	C29—C28—C27	120.4 (4)
C8—C3—C2	120.7 (4)	C29—C28—N4	119.6 (4)
C4—C3—C2	121.6 (4)	C27—C28—N4	119.9 (4)
C5—C4—C3	121.4 (4)	C28—C29—C30	120.2 (5)
C5—C4—H4	119.3	C28—C29—H29	119.9
C3—C4—H4	119.3	C30—C29—H29	119.9
C6—C5—C4	120.3 (4)	C25—C30—C29	120.6 (5)
C6—C5—H5	119.8	C25—C30—H30	119.7
C4—C5—H5	119.8	C29—C30—H30	119.7
C5—C6—C7	118.8 (4)	N4—C31—C32	127.6 (4)
C5—C6—N2	121.2 (4)	N4—C31—H31	116.2
C7—C6—N2	120.0 (4)	C32—C31—H31	116.2
C6—C7—C8	120.7 (4)	C33—C32—C37	120.5 (4)
C6—C7—H7	119.6	C33—C32—C31	122.3 (4)
C8—C7—H7	119.6	C37—C32—C31	117.2 (4)
C3—C8—C7	121.1 (4)	O4—C33—C32	123.8 (4)
C3—C8—H8	119.5	O4—C33—C34	120.7 (4)
C7—C8—H8	119.5	C32—C33—C34	115.5 (4)
N2—C9—C10	128.1 (4)	C35—C34—C33	123.2 (4)
N2—C9—H9	115.9	C35—C34—Br3	119.2 (3)
C10—C9—H9	115.9	C33—C34—Br3	117.6 (3)
C15—C10—C11	120.8 (4)	C34—C35—C36	119.6 (4)
C15—C10—C9	117.2 (4)	C34—C35—H35	120.2
C11—C10—C9	122.0 (4)	C36—C35—H35	120.2
O2—C11—C12	120.4 (4)	C37—C36—C35	120.1 (4)
O2—C11—C10	124.3 (3)	C37—C36—Br4	119.6 (3)
C12—C11—C10	115.2 (4)	C35—C36—Br4	120.3 (3)
C13—C12—C11	123.3 (4)	C36—C37—C32	120.9 (4)
C13—C12—Br1	119.1 (3)	C36—C37—H37	119.6
C11—C12—Br1	117.5 (3)	C32—C37—H37	119.6
C12—C13—C14	119.5 (4)	O3—C38—C39	111.4 (5)
C12—C13—H13	120.2	O3—C38—H38A	109.4
C14—C13—H13	120.2	C39—C38—H38A	109.4
C15—C14—C13	120.3 (4)	O3—C38—H38B	109.4
C15—C14—Br2	120.9 (3)	C39—C38—H38B	109.4
C13—C14—Br2	118.8 (3)	H38A—C38—H38B	108.0
C14—C15—C10	120.8 (4)	C44—C39—C40	117.2 (6)
C14—C15—H15	119.6	C44—C39—C38	121.2 (5)
C10—C15—H15	119.6	C40—C39—C38	121.6 (6)
O1—C16—C17	112.1 (4)	C41—C40—C39	119.4 (6)
O1—C16—H16A	109.2	C41—C40—H40	120.3
C17—C16—H16A	109.2	C39—C40—H40	120.3
O1—C16—H16B	109.2	C42—C41—C40	121.5 (6)
C17—C16—H16B	109.2	C42—C41—H41	119.2
H16A—C16—H16B	107.9	C40—C41—H41	119.2
C22—C17—C18	117.8 (5)	C43—C42—C41	119.4 (7)
C22—C17—C16	121.7 (5)	C43—C42—H42	120.3
C18—C17—C16	120.6 (5)	C41—C42—H42	120.3
C17—C18—C19	121.0 (5)	C42—C43—C44	120.4 (7)
C17—C18—H18	119.5	C42—C43—H43	119.8
C19—C18—H18	119.5	C44—C43—H43	119.8
C20—C19—C18	119.9 (5)	C43—C44—C39	122.0 (6)
C20—C19—H19	120.1	C43—C44—H44	119.0
C18—C19—H19	120.1	C39—C44—H44	119.0

O2—Cu1—N2—C9	5.8 (3)	C22—C17—C18—C19	0.4 (8)
O4—Cu1—N2—C9	−162.4 (3)	C16—C17—C18—C19	179.6 (5)
O2—Cu1—N2—C6	−178.4 (3)	C17—C18—C19—C20	−0.5 (8)
O4—Cu1—N2—C6	13.3 (3)	C18—C19—C20—C21	0.3 (9)
O2—Cu1—N4—C31	−165.0 (4)	C19—C20—C21—C22	0.1 (9)
O4—Cu1—N4—C31	3.0 (4)	C18—C17—C22—C21	0.0 (8)
O2—Cu1—N4—C28	12.1 (3)	C16—C17—C22—C21	−179.3 (5)
O4—Cu1—N4—C28	−179.9 (4)	C20—C21—C22—C17	−0.2 (9)
C2—N1—O1—C16	−176.9 (4)	O3—N3—C24—C25	−179.0 (3)
O4—Cu1—O2—C11	93.3 (6)	O3—N3—C24—C23	1.3 (6)
N4—Cu1—O2—C11	−179.9 (4)	N3—C24—C25—C30	9.1 (6)
N2—Cu1—O2—C11	−6.9 (4)	C23—C24—C25—C30	−171.1 (4)
C24—N3—O3—C38	−156.9 (4)	N3—C24—C25—C26	−168.6 (4)
O2—Cu1—O4—C33	79.9 (7)	C23—C24—C25—C26	11.1 (6)
N4—Cu1—O4—C33	−6.5 (4)	C30—C25—C26—C27	0.5 (7)
N2—Cu1—O4—C33	−179.7 (4)	C24—C25—C26—C27	178.2 (4)
O1—N1—C2—C3	176.8 (3)	C25—C26—C27—C28	1.1 (7)
O1—N1—C2—C1	−1.5 (6)	C26—C27—C28—C29	−2.3 (6)
N1—C2—C3—C8	−162.1 (4)	C26—C27—C28—N4	174.3 (4)
C1—C2—C3—C8	16.3 (7)	C31—N4—C28—C29	74.8 (5)
N1—C2—C3—C4	15.4 (7)	Cu1—N4—C28—C29	−102.5 (4)
C1—C2—C3—C4	−166.3 (4)	C31—N4—C28—C27	−101.9 (5)
C8—C3—C4—C5	−0.4 (7)	Cu1—N4—C28—C27	80.7 (5)
C2—C3—C4—C5	−177.9 (4)	C27—C28—C29—C30	2.0 (7)
C3—C4—C5—C6	2.0 (7)	N4—C28—C29—C30	−174.6 (4)
C4—C5—C6—C7	−2.7 (7)	C26—C25—C30—C29	−0.8 (7)
C4—C5—C6—N2	176.4 (4)	C24—C25—C30—C29	−178.5 (4)
C9—N2—C6—C5	−122.6 (4)	C28—C29—C30—C25	−0.5 (7)
Cu1—N2—C6—C5	61.4 (5)	C28—N4—C31—C32	−178.1 (4)
C9—N2—C6—C7	56.4 (5)	Cu1—N4—C31—C32	−0.8 (7)
Cu1—N2—C6—C7	−119.6 (4)	N4—C31—C32—C33	−0.1 (8)
C5—C6—C7—C8	1.8 (7)	N4—C31—C32—C37	179.5 (5)
N2—C6—C7—C8	−177.2 (4)	Cu1—O4—C33—C32	7.5 (7)
C4—C3—C8—C7	−0.5 (7)	Cu1—O4—C33—C34	−172.0 (3)
C2—C3—C8—C7	177.1 (4)	C37—C32—C33—O4	177.3 (4)
C6—C7—C8—C3	−0.3 (7)	C31—C32—C33—O4	−3.2 (7)
C6—N2—C9—C10	179.8 (4)	C37—C32—C33—C34	−3.3 (7)
Cu1—N2—C9—C10	−4.2 (6)	C31—C32—C33—C34	176.2 (4)
N2—C9—C10—C15	−178.1 (4)	O4—C33—C34—C35	−176.4 (4)
N2—C9—C10—C11	0.9 (7)	C32—C33—C34—C35	4.2 (7)
Cu1—O2—C11—C12	−174.0 (3)	O4—C33—C34—Br3	2.9 (6)
Cu1—O2—C11—C10	5.7 (6)	C32—C33—C34—Br3	−176.5 (3)
C15—C10—C11—O2	177.6 (4)	C33—C34—C35—C36	−2.1 (7)
C9—C10—C11—O2	−1.3 (7)	Br3—C34—C35—C36	178.6 (4)
C15—C10—C11—C12	−2.7 (6)	C34—C35—C36—C37	−0.9 (8)
C9—C10—C11—C12	178.4 (4)	C34—C35—C36—Br4	179.0 (4)
O2—C11—C12—C13	−177.2 (4)	C35—C36—C37—C32	1.7 (8)
C10—C11—C12—C13	3.0 (6)	Br4—C36—C37—C32	−178.3 (4)
O2—C11—C12—Br1	4.0 (5)	C33—C32—C37—C36	0.5 (7)
C10—C11—C12—Br1	−175.8 (3)	C31—C32—C37—C36	−179.0 (5)
C11—C12—C13—C14	−1.5 (7)	N3—O3—C38—C39	80.7 (5)
Br1—C12—C13—C14	177.3 (3)	O3—C38—C39—C44	−71.0 (7)
C12—C13—C14—C15	−0.6 (7)	O3—C38—C39—C40	106.2 (6)
C12—C13—C14—Br2	177.9 (3)	C44—C39—C40—C41	1.8 (9)
C13—C14—C15—C10	0.8 (7)	C38—C39—C40—C41	−175.5 (6)
Br2—C14—C15—C10	−177.6 (3)	C39—C40—C41—C42	0.6 (10)
C11—C10—C15—C14	0.9 (6)	C40—C41—C42—C43	−2.5 (11)
C9—C10—C15—C14	179.8 (4)	C41—C42—C43—C44	2.0 (10)
N1—O1—C16—C17	−96.1 (4)	C42—C43—C44—C39	0.5 (10)
O1—C16—C17—C22	75.4 (6)	C40—C39—C44—C43	−2.4 (9)
O1—C16—C17—C18	−103.8 (5)	C38—C39—C44—C43	174.9 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the Cu/O4/C33–C31/N4 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···Cg1ⁱ	0.93	2.82	3.575 (5)	118
C16—H16B···Cg2ⁱ	0.97	2.96	3.511 (5)	117

Symmetry code: (i) −x+1/2, y+3/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cu(C₂₂H₁₇Br₂N₂O₂)₂]
M_r	1065.93
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	27.4484 (7), 13.3116 (3), 22.3609 (5)
β (°)	91.165 (2)
V (Å³)	8168.6 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	4.50
Crystal size (mm)	0.30 × 0.21 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.346, 0.662
No. of measured, independent and observed [I > 2σ(I)] reflections	27775, 7199, 4682
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.078, 1.01
No. of reflections	7199
No. of parameters	514
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.36

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the Cu/O4/C33–C31/N4 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···Cg1ⁱ	0.93	2.82	3.575 (5)	118
C16—H16B···Cg2ⁱ	0.97	2.96	3.511 (5)	117

Symmetry code: (i) −x+1/2, y+3/2, −z+1/2.

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (0904–11), which is gratefully acknowledged.

References

Akine, S., Taniguchi, T. & Nabeshima, T. (2001). Chem. Lett. 30, 682–683. CSD CrossRef Google Scholar
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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis[2,4-di­bromo-6-(N-{4-[(E)-1-(benzyl­­oxy­imino)­eth­yl]phen­yl}carboximido­yl)phenolato]copper(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[2,4-dibromo-6-(N-{4-[(E)-1-(benzyloxyimino)ethyl]phenyl}carboximidoyl)phenolato]copper(II)