Dibromido{2-hydr­oxy-N′-[phen­yl(2-pyrid­yl)methyl­ene]benzohydrazide}copper(II)

Kong, L.-Q.; Ju, X.-P.; Li, D.-C.

doi:10.1107/S1600536809038070

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page m1251

doi:10.1107/S1600536809038070

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Dibromido{2-hydroxy-N′-[phenyl(2-pyridyl)methylene]benzohydrazide}copper(II)

Ling-Qian Kong,^a,^b Xiu-Ping Ju ^a and Da-Cheng Li ^b ^*

^aDongchang College of Liaocheng University, Shandong 25200, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: lidacheng@lcu.edu.cn

(Received 17 September 2009; accepted 21 September 2009; online 26 September 2009)

In the title complex, [CuBr₂(C₁₉H₁₅N₃O₂)], the metal ion is coordinated by the N,N′,O-tridentate 2-hydroxy-N′-[phenyl(2-pyridyl)methylene]benzohydrazide ligand and two bromide ions, resulting in a distorted CuN₂OBr₂ square-based pyramidal coordination geometry with one bromide ion in the apical site. An intramolecular N—H⋯O hydrogen bond occurs in the ligand. In the crystal, molecules are connected by intermolecular C—H⋯O, C—H⋯Br and O—H⋯Br interactions.

Related literature

For the crystal structures of metal complexes with 2-benzoylpyridine salicyloylhydrazone, see: Sur et al. (1993 ); Seth & Chakraborty (1984 ); Dan et al. (1989 ).

Experimental

Crystal data

[CuBr₂(C₁₉H₁₅N₃O₂)]
M_r = 540.70
Monoclinic, P 2₁ /n
a = 8.0779 (11) Å
b = 16.302 (2) Å
c = 15.0376 (18) Å
β = 97.624 (2)°
V = 1962.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 5.20 mm⁻¹
T = 298 K
0.23 × 0.19 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.381, T_max = 0.509
8676 measured reflections
3446 independent reflections
2426 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.082
S = 1.01
3446 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.94 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—N2	1.966 (3)
Cu1—N3	2.018 (3)
Cu1—O1	2.083 (2)
Cu1—Br1	2.3469 (6)
Cu1—Br2	2.5931 (8)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	1.92	2.574 (4)	131
O2—H2⋯Br2ⁱ	0.82	2.35	3.153 (3)	166
C11—H11⋯O1ⁱⁱ	0.93	2.58	3.503 (5)	170
C10—H10⋯Br1ⁱⁱ	0.93	2.81	3.575 (4)	141
C15—H15⋯Br2ⁱⁱⁱ	0.93	2.82	3.742 (4)	171
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z.

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); 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 I, global. DOI: 10.1107/S1600536809038070/hb5107sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809038070/hb5107Isup2.hkl

checkCIF report

Comment top

A large number of salicyloylhydrazone complexes have been reported and studied. However, the metal complexes of 2-benzoylpyridine salicyloylhydrazone reported are limited to Zn (Sur et al., 1993), Ni (Seth et al., 1984) and (Dan et al., 1989). Here, we have synthesized and will report a new 2-benzoylpyridine salicyloylhydrazone complex Cu₍C₁₉H₁₅N₃O₂)Br₂, which was was characterized by X-ray diffraction and elemental analysis. The crystals suitable for X-ray diffraction studies were obtained by slow evaporation of the mother liquid. In this paper, we will display the crystal structure of the title complex.

The title complex(Fig.1), Cu₍C₁₉H₁₅N₃O₂)Br₂ is composed of a Cu atom, a 2-benzoylpyridine salicyloylhydrazone ligand molecule and two bromines. The ligand is bound to Cu atom by a carbonyl O, a pyridine N and a hydrazone N to form two juxtaposed five-membered chelate rings. Cu lies in a five-coordinated and square-pyramid coordination geometry with the _ON₂Br₂ set of donor atoms. The equatorial coordination sits are occupied by O1, N2, N3, Br1 and the axial coordination atom is Br2 with the distance of Cu1—Br2 2.5931 (8) A. In the structure, there are intramolecular N—H···O interactions. Except that, the complex is linked into one-dimensional chain by intermolecular C—H···Br interactions, and the neighboring chains form a two-dimensional network structure via C—H···Br and O—H···Br interactions. A three-dimensional network structure is connected via C—H···O and C—H···Br interactions between adjacent two-dimensional networks. So the complex is linked into a three-dimensional network structure via intermolecular C—H···O, C—H···Br and O—H···Br interactions.

Related literature top

For the crystal structures of metal complexes with 2-benzoylpyridine salicyloylhydrazone, see: Sur et al. (1993); Seth et al. (1984); Dan et al. (1989).

Experimental top

CuBr₂.H₂O (0.25 mmol 0.065 g) was dissolved in 10 ml MeOH and a 10 ml 1,1-dichlorinemethane solution of 2-benzoylpyridine salicyloylhydrazone (0.25 mmol 0.080 g) was added dropwise to the former. The mixture was stirred for six hours until the solution color became dark green.The dark green solution was stirred for five hours and filtered. The filtrate layered with Et₂O to resulted in dark green blocks of (I) at room temperature. m.p.>573 K. Elemental analysis for _C19_H15_CuN₃O₂Br₂ calculated: C 42.21, H 2.80 N 7.77%; found: C 42.32, H 2.54, N 7.68%.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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 (I) showing 30% displacement ellipsoids. C-bound H atoms have been omitted for clarity.

Dibromido{2-hydroxy-N'-[phenyl(2- pyridyl)methylene]benzohydrazide}copper(II) top

Crystal data top

[CuBr₂(C₁₉H₁₅N₃O₂)]	F(000) = 1060
M_r = 540.70	D_x = 1.830 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2246 reflections
a = 8.0779 (11) Å	θ = 2.5–25.1°
b = 16.302 (2) Å	µ = 5.20 mm⁻¹
c = 15.0376 (18) Å	T = 298 K
β = 97.624 (2)°	Block, dark green
V = 1962.8 (4) Å³	0.23 × 0.19 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3446 independent reflections
Radiation source: fine-focus sealed tube	2426 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −9→9
T_min = 0.381, T_max = 0.509	k = −17→19
8676 measured reflections	l = −17→11

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0396P)²] where P = (F_o² + 2F_c²)/3
3446 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.94 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

[CuBr₂(C₁₉H₁₅N₃O₂)]	V = 1962.8 (4) Å³
M_r = 540.70	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0779 (11) Å	µ = 5.20 mm⁻¹
b = 16.302 (2) Å	T = 298 K
c = 15.0376 (18) Å	0.23 × 0.19 × 0.15 mm
β = 97.624 (2)°

Data collection top

Bruker SMART CCD diffractometer	3446 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	2426 reflections with I > 2σ(I)
T_min = 0.381, T_max = 0.509	R_int = 0.034
8676 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.01	Δρ_max = 0.94 e Å⁻³
3446 reflections	Δρ_min = −0.58 e Å⁻³
244 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	0.63317 (6)	0.70295 (3)	0.15437 (3)	0.03541 (16)
Br1	0.63665 (6)	0.81344 (2)	0.05459 (3)	0.04420 (15)
Br2	0.92790 (7)	0.70189 (3)	0.24686 (4)	0.06244 (18)
N1	0.5874 (4)	0.53300 (18)	0.1785 (2)	0.0390 (9)
H1	0.5667	0.4870	0.2027	0.047*
N2	0.5516 (4)	0.60651 (17)	0.2140 (2)	0.0349 (8)
N3	0.5009 (4)	0.75634 (19)	0.2434 (2)	0.0347 (8)
O1	0.6872 (4)	0.60672 (14)	0.07174 (18)	0.0389 (7)
O2	0.5854 (4)	0.37576 (16)	0.1626 (2)	0.0585 (10)
H2	0.5800	0.3273	0.1765	0.088*
C1	0.6586 (5)	0.5380 (2)	0.1020 (3)	0.0337 (10)
C2	0.7003 (5)	0.4611 (2)	0.0589 (3)	0.0341 (10)
C3	0.6649 (5)	0.3826 (2)	0.0886 (3)	0.0392 (11)
C4	0.7099 (6)	0.3140 (2)	0.0427 (3)	0.0481 (12)
H4	0.6868	0.2618	0.0625	0.058*
C5	0.7887 (6)	0.3237 (3)	−0.0321 (3)	0.0523 (13)
H5	0.8161	0.2774	−0.0631	0.063*
C6	0.8283 (6)	0.3997 (3)	−0.0622 (3)	0.0530 (13)
H6	0.8842	0.4053	−0.1121	0.064*
C7	0.7826 (6)	0.4679 (2)	−0.0164 (3)	0.0453 (12)
H7	0.8076	0.5198	−0.0365	0.054*
C8	0.4677 (5)	0.6152 (2)	0.2817 (3)	0.0347 (10)
C9	0.4411 (5)	0.7033 (2)	0.3016 (3)	0.0330 (10)
C10	0.3652 (5)	0.7305 (2)	0.3723 (3)	0.0382 (11)
H10	0.3305	0.6934	0.4131	0.046*
C11	0.3407 (6)	0.8137 (2)	0.3823 (3)	0.0464 (12)
H11	0.2869	0.8332	0.4290	0.056*
C12	0.3965 (6)	0.8670 (2)	0.3226 (3)	0.0474 (12)
H12	0.3790	0.9232	0.3275	0.057*
C13	0.4786 (6)	0.8367 (2)	0.2553 (3)	0.0441 (12)
H13	0.5204	0.8735	0.2166	0.053*
C14	0.4049 (5)	0.5474 (2)	0.3330 (3)	0.0323 (10)
C15	0.2398 (5)	0.5486 (2)	0.3512 (3)	0.0410 (11)
H15	0.1692	0.5914	0.3300	0.049*
C16	0.1819 (6)	0.4863 (2)	0.4004 (3)	0.0466 (12)
H16	0.0725	0.4878	0.4133	0.056*
C17	0.2839 (6)	0.4219 (3)	0.4306 (3)	0.0530 (13)
H17	0.2435	0.3798	0.4634	0.064*
C18	0.4474 (6)	0.4201 (3)	0.4120 (3)	0.0520 (13)
H18	0.5165	0.3763	0.4319	0.062*
C19	0.5076 (5)	0.4825 (2)	0.3643 (3)	0.0428 (11)
H19	0.6180	0.4814	0.3529	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0471 (3)	0.0269 (3)	0.0353 (3)	0.0016 (2)	0.0168 (3)	0.0001 (2)
Br1	0.0552 (3)	0.0367 (2)	0.0453 (3)	0.0031 (2)	0.0238 (2)	0.0088 (2)
Br2	0.0575 (3)	0.0528 (3)	0.0716 (4)	0.0197 (2)	−0.0113 (3)	−0.0204 (3)
N1	0.057 (2)	0.0228 (17)	0.042 (2)	0.0029 (15)	0.0223 (19)	−0.0013 (15)
N2	0.048 (2)	0.0262 (18)	0.033 (2)	0.0023 (15)	0.0149 (18)	−0.0039 (15)
N3	0.041 (2)	0.0322 (19)	0.033 (2)	0.0046 (15)	0.0129 (17)	0.0022 (15)
O1	0.060 (2)	0.0265 (15)	0.0343 (18)	−0.0017 (13)	0.0203 (15)	−0.0002 (12)
O2	0.086 (3)	0.0286 (16)	0.068 (2)	−0.0033 (15)	0.038 (2)	0.0041 (15)
C1	0.038 (3)	0.034 (2)	0.031 (3)	0.0028 (18)	0.010 (2)	0.0000 (19)
C2	0.039 (3)	0.025 (2)	0.038 (3)	−0.0001 (17)	0.007 (2)	−0.0042 (18)
C3	0.042 (3)	0.031 (2)	0.046 (3)	−0.0022 (19)	0.009 (2)	−0.004 (2)
C4	0.053 (3)	0.026 (2)	0.066 (3)	−0.001 (2)	0.008 (3)	−0.004 (2)
C5	0.069 (4)	0.038 (3)	0.049 (3)	0.010 (2)	0.007 (3)	−0.014 (2)
C6	0.075 (4)	0.045 (3)	0.043 (3)	0.008 (2)	0.021 (3)	−0.009 (2)
C7	0.062 (3)	0.033 (2)	0.044 (3)	0.001 (2)	0.016 (3)	0.004 (2)
C8	0.034 (2)	0.034 (2)	0.036 (3)	−0.0020 (18)	0.005 (2)	−0.0017 (19)
C9	0.038 (3)	0.032 (2)	0.030 (2)	0.0024 (18)	0.009 (2)	0.0025 (18)
C10	0.049 (3)	0.036 (2)	0.033 (3)	−0.0011 (19)	0.016 (2)	−0.0008 (19)
C11	0.058 (3)	0.046 (3)	0.039 (3)	0.006 (2)	0.020 (2)	−0.006 (2)
C12	0.073 (4)	0.031 (2)	0.040 (3)	0.008 (2)	0.016 (3)	−0.002 (2)
C13	0.065 (3)	0.028 (2)	0.042 (3)	0.007 (2)	0.016 (3)	0.003 (2)
C14	0.040 (3)	0.030 (2)	0.029 (2)	0.0015 (18)	0.009 (2)	0.0044 (18)
C15	0.040 (3)	0.034 (2)	0.050 (3)	0.0055 (19)	0.009 (2)	0.001 (2)
C16	0.041 (3)	0.042 (3)	0.060 (3)	−0.009 (2)	0.020 (3)	−0.003 (2)
C17	0.071 (4)	0.039 (3)	0.052 (3)	−0.011 (2)	0.019 (3)	0.009 (2)
C18	0.066 (3)	0.037 (3)	0.054 (3)	0.011 (2)	0.014 (3)	0.015 (2)
C19	0.041 (3)	0.045 (3)	0.045 (3)	0.005 (2)	0.012 (2)	0.006 (2)

Geometric parameters (Å, º) top

Cu1—N2	1.966 (3)	C6—H6	0.9300
Cu1—N3	2.018 (3)	C7—H7	0.9300
Cu1—O1	2.083 (2)	C8—C14	1.474 (5)
Cu1—Br1	2.3469 (6)	C8—C9	1.490 (5)
Cu1—Br2	2.5931 (8)	C9—C10	1.370 (5)
N1—C1	1.355 (5)	C10—C11	1.381 (5)
N1—N2	1.358 (4)	C10—H10	0.9300
N1—H1	0.8600	C11—C12	1.369 (6)
N2—C8	1.304 (5)	C11—H11	0.9300
N3—C13	1.338 (5)	C12—C13	1.373 (5)
N3—C9	1.363 (5)	C12—H12	0.9300
O1—C1	1.242 (4)	C13—H13	0.9300
O2—C3	1.361 (5)	C14—C19	1.388 (5)
O2—H2	0.8200	C14—C15	1.397 (5)
C1—C2	1.471 (5)	C15—C16	1.375 (5)
C2—C7	1.393 (5)	C15—H15	0.9300
C2—C3	1.396 (5)	C16—C17	1.374 (6)
C3—C4	1.388 (5)	C16—H16	0.9300
C4—C5	1.373 (6)	C17—C18	1.386 (6)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.373 (6)	C18—C19	1.371 (5)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.383 (5)	C19—H19	0.9300

N2—Cu1—N3	78.67 (12)	C6—C7—C2	121.9 (4)
N2—Cu1—O1	77.25 (11)	C6—C7—H7	119.0
N3—Cu1—O1	153.13 (12)	C2—C7—H7	119.0
N2—Cu1—Br1	159.76 (10)	N2—C8—C14	125.3 (3)
N3—Cu1—Br1	98.37 (9)	N2—C8—C9	111.4 (3)
O1—Cu1—Br1	100.10 (7)	C14—C8—C9	123.3 (3)
N2—Cu1—Br2	95.15 (10)	N3—C9—C10	121.8 (3)
N3—Cu1—Br2	100.15 (10)	N3—C9—C8	114.2 (3)
O1—Cu1—Br2	93.71 (8)	C10—C9—C8	124.0 (3)
Br1—Cu1—Br2	105.07 (2)	C9—C10—C11	119.2 (4)
C1—N1—N2	114.6 (3)	C9—C10—H10	120.4
C1—N1—H1	122.7	C11—C10—H10	120.4
N2—N1—H1	122.7	C12—C11—C10	119.2 (4)
C8—N2—N1	124.2 (3)	C12—C11—H11	120.4
C8—N2—Cu1	120.7 (2)	C10—C11—H11	120.4
N1—N2—Cu1	115.1 (2)	C11—C12—C13	119.2 (4)
C13—N3—C9	118.0 (3)	C11—C12—H12	120.4
C13—N3—Cu1	127.2 (3)	C13—C12—H12	120.4
C9—N3—Cu1	114.6 (2)	N3—C13—C12	122.6 (4)
C1—O1—Cu1	113.3 (2)	N3—C13—H13	118.7
C3—O2—H2	109.5	C12—C13—H13	118.7
O1—C1—N1	119.1 (3)	C19—C14—C15	119.2 (3)
O1—C1—C2	122.9 (4)	C19—C14—C8	121.1 (4)
N1—C1—C2	118.0 (3)	C15—C14—C8	119.7 (3)
C7—C2—C3	118.3 (4)	C16—C15—C14	119.8 (4)
C7—C2—C1	116.9 (3)	C16—C15—H15	120.1
C3—C2—C1	124.9 (4)	C14—C15—H15	120.1
O2—C3—C4	121.6 (4)	C17—C16—C15	120.7 (4)
O2—C3—C2	118.4 (3)	C17—C16—H16	119.7
C4—C3—C2	120.0 (4)	C15—C16—H16	119.7
C5—C4—C3	119.7 (4)	C16—C17—C18	119.7 (4)
C5—C4—H4	120.1	C16—C17—H17	120.1
C3—C4—H4	120.1	C18—C17—H17	120.1
C4—C5—C6	121.9 (4)	C19—C18—C17	120.2 (4)
C4—C5—H5	119.1	C19—C18—H18	119.9
C6—C5—H5	119.1	C17—C18—H18	119.9
C5—C6—C7	118.2 (4)	C18—C19—C14	120.4 (4)
C5—C6—H6	120.9	C18—C19—H19	119.8
C7—C6—H6	120.9	C14—C19—H19	119.8

C1—N1—N2—C8	172.6 (4)	C3—C4—C5—C6	1.5 (8)
C1—N1—N2—Cu1	−6.5 (4)	C4—C5—C6—C7	−1.7 (8)
N3—Cu1—N2—C8	−4.6 (3)	C5—C6—C7—C2	0.7 (7)
O1—Cu1—N2—C8	−172.6 (3)	C3—C2—C7—C6	0.5 (7)
Br1—Cu1—N2—C8	−88.0 (4)	C1—C2—C7—C6	179.9 (4)
Br2—Cu1—N2—C8	94.8 (3)	N1—N2—C8—C14	2.8 (6)
N3—Cu1—N2—N1	174.6 (3)	Cu1—N2—C8—C14	−178.1 (3)
O1—Cu1—N2—N1	6.6 (3)	N1—N2—C8—C9	−176.9 (4)
Br1—Cu1—N2—N1	91.2 (4)	Cu1—N2—C8—C9	2.2 (5)
Br2—Cu1—N2—N1	−86.1 (3)	C13—N3—C9—C10	−2.2 (6)
N2—Cu1—N3—C13	−179.8 (4)	Cu1—N3—C9—C10	172.6 (3)
O1—Cu1—N3—C13	−153.1 (3)	C13—N3—C9—C8	178.5 (4)
Br1—Cu1—N3—C13	−20.1 (4)	Cu1—N3—C9—C8	−6.8 (4)
Br2—Cu1—N3—C13	87.0 (3)	N2—C8—C9—N3	3.1 (5)
N2—Cu1—N3—C9	6.0 (3)	C14—C8—C9—N3	−176.6 (4)
O1—Cu1—N3—C9	32.7 (5)	N2—C8—C9—C10	−176.2 (4)
Br1—Cu1—N3—C9	165.7 (3)	C14—C8—C9—C10	4.1 (7)
Br2—Cu1—N3—C9	−87.2 (3)	N3—C9—C10—C11	3.4 (7)
N2—Cu1—O1—C1	−6.0 (3)	C8—C9—C10—C11	−177.3 (4)
N3—Cu1—O1—C1	−32.8 (5)	C9—C10—C11—C12	−1.6 (7)
Br1—Cu1—O1—C1	−165.6 (3)	C10—C11—C12—C13	−1.4 (7)
Br2—Cu1—O1—C1	88.4 (3)	C9—N3—C13—C12	−0.9 (6)
Cu1—O1—C1—N1	4.5 (5)	Cu1—N3—C13—C12	−174.9 (3)
Cu1—O1—C1—C2	−174.8 (3)	C11—C12—C13—N3	2.7 (7)
N2—N1—C1—O1	1.1 (6)	N2—C8—C14—C19	48.2 (6)
N2—N1—C1—C2	−179.6 (3)	C9—C8—C14—C19	−132.1 (4)
O1—C1—C2—C7	3.1 (6)	N2—C8—C14—C15	−132.3 (4)
N1—C1—C2—C7	−176.1 (4)	C9—C8—C14—C15	47.4 (6)
O1—C1—C2—C3	−177.5 (4)	C19—C14—C15—C16	0.7 (6)
N1—C1—C2—C3	3.2 (6)	C8—C14—C15—C16	−178.8 (4)
C7—C2—C3—O2	179.6 (4)	C14—C15—C16—C17	−1.2 (7)
C1—C2—C3—O2	0.3 (6)	C15—C16—C17—C18	0.5 (7)
C7—C2—C3—C4	−0.7 (7)	C16—C17—C18—C19	0.6 (7)
C1—C2—C3—C4	180.0 (4)	C17—C18—C19—C14	−1.1 (7)
O2—C3—C4—C5	179.5 (4)	C15—C14—C19—C18	0.4 (7)
C2—C3—C4—C5	−0.2 (7)	C8—C14—C19—C18	179.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.92	2.574 (4)	131
O2—H2···Br2ⁱ	0.82	2.35	3.153 (3)	166
C11—H11···O1ⁱⁱ	0.93	2.58	3.503 (5)	170
C10—H10···Br1ⁱⁱ	0.93	2.81	3.575 (4)	141
C15—H15···Br2ⁱⁱⁱ	0.93	2.82	3.742 (4)	171

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+3/2, z+1/2; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[CuBr₂(C₁₉H₁₅N₃O₂)]
M_r	540.70
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.0779 (11), 16.302 (2), 15.0376 (18)
β (°)	97.624 (2)
V (Å³)	1962.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.20
Crystal size (mm)	0.23 × 0.19 × 0.15

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.381, 0.509
No. of measured, independent and observed [I > 2σ(I)] reflections	8676, 3446, 2426
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.082, 1.01
No. of reflections	3446
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.94, −0.58

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—N2	1.966 (3)	Cu1—Br1	2.3469 (6)
Cu1—N3	2.018 (3)	Cu1—Br2	2.5931 (8)
Cu1—O1	2.083 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.92	2.574 (4)	131
O2—H2···Br2ⁱ	0.82	2.35	3.153 (3)	166
C11—H11···O1ⁱⁱ	0.93	2.58	3.503 (5)	170
C10—H10···Br1ⁱⁱ	0.93	2.81	3.575 (4)	141
C15—H15···Br2ⁱⁱⁱ	0.93	2.82	3.742 (4)	171

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+3/2, z+1/2; (iii) x−1, y, z.

Acknowledgements

We acknowledge the financial support of the National Natural Science Foundation of China (grant No. 20671048).

References

Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dan, J., Seth, S. & Chakraborty, S. (1989). Acta Cryst. C45, 1018–1021. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Seth, S. & Chakraborty, S. (1984). Acta Cryst. C40, 1530–1533. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sur, H., Roychowdhuri, S. & Seth, S. (1993). Acta Cryst. C49, 870–873. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar

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Volume 65| Part 10| October 2009| Page m1251

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

Di­bromido{2-hydr­­oxy-N′-[phen­yl(2-pyrid­yl)methyl­ene]benzohydrazide}copper(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Dibromido{2-hydroxy-N′-[phenyl(2-pyridyl)methylene]benzohydrazide}copper(II)