Bis{2-bromo-4-chloro-6-[2-(phenyl-sulfon-yl)hydrazonometh-yl]phenolato-κN,O}copper(II).

The Cu atom in the title compound, [Cu(C(13)H(9)BrClN(2)O(3)S)(2)], is chelated by two deprotonated Schiff base ligands in a square-planar coordination geometry; the Cu atom lies on a center of inversion. The -NH- group of one anion forms an intra-molecular hydrogen bond to the phenolate atom of the symmetry-related ion.

Related literature

For the structure of the copper derivative of a similar Schiff base ligand, see: Ali et al. (2007 ▶).

Experimental

Crystal data

[Cu(C13H9BrClN2O3S)2]

M = 840.82

Triclinic,

a = 8.0688 (1) Å

b = 8.2755 (1) Å

c = 11.7386 (2) Å

α = 95.955 (1)°

β = 90.133 (1)°

γ = 115.159 (1)°

V = 704.70 (2) Å3

Z = 1

Mo Kα radiation

μ = 4.00 mm−1

T = 100 (2) K

0.20 × 0.09 × 0.09 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.502, T max = 0.715

8995 measured reflections

3214 independent reflections

2928 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.061

S = 1.05

3214 reflections

200 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022022/hg2424sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022022/hg2424Isup2.hkl

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

[Cu(C13H9BrClN2O3S)2]	Z = 1
Mr = 840.82	F000 = 415
Triclinic, P1	Dx = 1.981 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.0688 (1) Å	Cell parameters from 5423 reflections
b = 8.2755 (1) Å	θ = 2.7–28.4º
c = 11.7386 (2) Å	µ = 4.00 mm−1
α = 95.955 (1)º	T = 100 (2) K
β = 90.133 (1)º	Block, purple
γ = 115.159 (1)º	0.20 × 0.09 × 0.09 mm
V = 704.70 (2) Å3

Bruker SMART APEX diffractometer	3214 independent reflections
Radiation source: fine-focus sealed tube	2928 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.017
T = 100(2) K	θmax = 27.5º
ω scans	θmin = 1.8º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)	h = −8→10
Tmin = 0.502, Tmax = 0.715	k = −10→10
8995 measured reflections	l = −15→15

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)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.061	w = 1/[σ2(Fo2) + (0.0332P)2 + 0.5714P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3214 reflections	Δρmax = 0.52 e Å−3
200 parameters	Δρmin = −0.29 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
Br1	0.46994 (3)	0.68016 (3)	0.125566 (17)	0.01926 (7)
Cu1	0.5000	0.5000	0.5000	0.01271 (9)
Cl1	−0.18066 (7)	0.07143 (7)	0.02818 (4)	0.02134 (12)
S1	0.09184 (7)	0.33794 (7)	0.69365 (4)	0.01590 (11)
O1	0.4287 (2)	0.53987 (19)	0.35457 (12)	0.0156 (3)
O2	−0.0713 (2)	0.2946 (2)	0.62483 (13)	0.0201 (3)
O3	0.0825 (2)	0.2833 (2)	0.80598 (13)	0.0223 (3)
N1	0.2591 (2)	0.2994 (2)	0.51073 (14)	0.0139 (3)
N2	0.2075 (2)	0.2348 (2)	0.62019 (14)	0.0149 (3)
H2N	0.309 (2)	0.267 (4)	0.663 (2)	0.025 (7)*
C1	0.2899 (3)	0.4324 (3)	0.28525 (17)	0.0142 (4)
C2	0.2784 (3)	0.4722 (3)	0.17138 (17)	0.0150 (4)
C3	0.1374 (3)	0.3636 (3)	0.09341 (17)	0.0165 (4)
H3	0.1350	0.3938	0.0177	0.020*
C4	−0.0018 (3)	0.2085 (3)	0.12702 (17)	0.0161 (4)
C5	0.0002 (3)	0.1631 (3)	0.23553 (17)	0.0162 (4)
H5	−0.0958	0.0571	0.2570	0.019*
C6	0.1451 (3)	0.2739 (3)	0.31582 (16)	0.0140 (4)
C7	0.1325 (3)	0.2211 (3)	0.42942 (17)	0.0151 (4)
H7	0.0238	0.1219	0.4461	0.018*
C8	0.2345 (3)	0.5685 (3)	0.69679 (18)	0.0168 (4)
C9	0.2357 (3)	0.6526 (3)	0.60000 (18)	0.0175 (4)
H9	0.1500	0.5902	0.5372	0.021*
C10	0.3634 (3)	0.8287 (3)	0.5961 (2)	0.0215 (4)
H10	0.3658	0.8877	0.5305	0.026*
C11	0.4881 (3)	0.9189 (3)	0.6887 (2)	0.0254 (5)
H11	0.5770	1.0388	0.6856	0.030*
C12	0.4833 (3)	0.8350 (3)	0.7848 (2)	0.0269 (5)
H12	0.5673	0.8987	0.8481	0.032*
C13	0.3572 (3)	0.6584 (3)	0.79044 (19)	0.0216 (4)
H13	0.3547	0.6004	0.8566	0.026*

	U11	U22	U33	U12	U13	U23
Br1	0.02148 (12)	0.01787 (11)	0.01395 (11)	0.00366 (9)	−0.00187 (8)	0.00401 (7)
Cu1	0.01245 (17)	0.01403 (16)	0.00878 (16)	0.00304 (13)	−0.00122 (12)	0.00080 (12)
Cl1	0.0154 (2)	0.0276 (3)	0.0122 (2)	0.0018 (2)	−0.00463 (18)	−0.00208 (19)
S1	0.0156 (2)	0.0193 (2)	0.0112 (2)	0.0056 (2)	0.00112 (18)	0.00311 (18)
O1	0.0151 (7)	0.0171 (7)	0.0111 (7)	0.0035 (6)	−0.0023 (5)	0.0018 (5)
O2	0.0148 (7)	0.0249 (8)	0.0179 (7)	0.0054 (6)	0.0001 (6)	0.0047 (6)
O3	0.0253 (8)	0.0291 (8)	0.0123 (7)	0.0107 (7)	0.0031 (6)	0.0054 (6)
N1	0.0167 (9)	0.0141 (8)	0.0095 (8)	0.0052 (7)	0.0006 (6)	0.0018 (6)
N2	0.0160 (9)	0.0166 (8)	0.0106 (8)	0.0051 (7)	−0.0009 (6)	0.0029 (6)
C1	0.0146 (10)	0.0162 (9)	0.0121 (9)	0.0074 (8)	−0.0016 (7)	−0.0007 (7)
C2	0.0161 (10)	0.0148 (9)	0.0134 (9)	0.0061 (8)	0.0005 (8)	0.0012 (7)
C3	0.0181 (10)	0.0214 (10)	0.0111 (9)	0.0096 (9)	−0.0002 (8)	0.0014 (8)
C4	0.0132 (10)	0.0196 (10)	0.0129 (9)	0.0060 (8)	−0.0037 (7)	−0.0043 (7)
C5	0.0145 (10)	0.0171 (9)	0.0149 (9)	0.0055 (8)	0.0002 (8)	−0.0014 (7)
C6	0.0147 (10)	0.0158 (9)	0.0112 (9)	0.0064 (8)	−0.0006 (7)	0.0003 (7)
C7	0.0155 (10)	0.0140 (9)	0.0139 (9)	0.0048 (8)	0.0003 (8)	0.0005 (7)
C8	0.0162 (10)	0.0177 (9)	0.0158 (9)	0.0074 (8)	0.0002 (8)	−0.0015 (8)
C9	0.0160 (10)	0.0184 (10)	0.0165 (10)	0.0062 (8)	−0.0006 (8)	0.0001 (8)
C10	0.0200 (11)	0.0198 (10)	0.0242 (11)	0.0079 (9)	0.0035 (9)	0.0027 (9)
C11	0.0190 (11)	0.0190 (11)	0.0330 (13)	0.0053 (9)	0.0000 (10)	−0.0058 (9)
C12	0.0247 (12)	0.0260 (12)	0.0257 (12)	0.0101 (10)	−0.0090 (9)	−0.0118 (9)
C13	0.0249 (12)	0.0246 (11)	0.0169 (10)	0.0137 (9)	−0.0039 (9)	−0.0047 (8)

Br1—C2	1.890 (2)	C3—H3	0.9500
Cu1—O1	1.905 (1)	C4—C5	1.367 (3)
Cu1—O1i	1.905 (1)	C5—C6	1.415 (3)
Cu1—N1i	1.963 (2)	C5—H5	0.9500
Cu1—N1	1.963 (2)	C6—C7	1.436 (3)
Cl1—C4	1.744 (2)	C7—H7	0.9500
S1—O3	1.4297 (15)	C8—C9	1.391 (3)
S1—O2	1.4309 (16)	C8—C13	1.393 (3)
S1—N2	1.6945 (19)	C9—C10	1.387 (3)
S1—C8	1.756 (2)	C9—H9	0.9500
O1—C1	1.306 (2)	C10—C11	1.393 (3)
N1—C7	1.296 (3)	C10—H10	0.9500
N1—N2	1.437 (2)	C11—C12	1.376 (4)
N2—H2N	0.88 (1)	C11—H11	0.9500
C1—C6	1.418 (3)	C12—C13	1.390 (3)
C1—C2	1.421 (3)	C12—H12	0.9500
C2—C3	1.377 (3)	C13—H13	0.9500
C3—C4	1.395 (3)
O1—Cu1—O1i	180.000 (1)	C5—C4—Cl1	119.90 (16)
O1—Cu1—N1	91.28 (6)	C3—C4—Cl1	119.02 (15)
O1—Cu1—N1i	88.72 (6)	C4—C5—C6	120.01 (19)
O1i—Cu1—N1i	91.28 (6)	C4—C5—H5	120.0
O1i—Cu1—N1	88.72 (6)	C6—C5—H5	120.0
N1i—Cu1—N1	180.0	C5—C6—C1	120.83 (18)
O3—S1—O2	120.99 (10)	C5—C6—C7	116.47 (18)
O3—S1—N2	104.25 (9)	C1—C6—C7	122.65 (18)
O2—S1—N2	105.94 (9)	N1—C7—C6	124.48 (19)
O3—S1—C8	110.55 (10)	N1—C7—H7	117.8
O2—S1—C8	109.09 (10)	C6—C7—H7	117.8
N2—S1—C8	104.59 (10)	C9—C8—C13	121.3 (2)
C1—O1—Cu1	128.38 (13)	C9—C8—S1	118.74 (16)
C7—N1—N2	114.29 (17)	C13—C8—S1	119.62 (17)
C7—N1—Cu1	126.86 (14)	C10—C9—C8	119.2 (2)
N2—N1—Cu1	118.75 (12)	C10—C9—H9	120.4
N1—N2—S1	112.10 (13)	C8—C9—H9	120.4
N1—N2—H2N	107.8 (18)	C9—C10—C11	119.9 (2)
S1—N2—H2N	103.9 (18)	C9—C10—H10	120.1
O1—C1—C6	124.07 (18)	C11—C10—H10	120.1
O1—C1—C2	119.77 (18)	C12—C11—C10	120.3 (2)
C6—C1—C2	116.16 (18)	C12—C11—H11	119.9
C3—C2—C1	122.80 (19)	C10—C11—H11	119.9
C3—C2—Br1	119.33 (15)	C11—C12—C13	120.9 (2)
C1—C2—Br1	117.84 (15)	C11—C12—H12	119.5
C2—C3—C4	119.11 (18)	C13—C12—H12	119.5
C2—C3—H3	120.4	C12—C13—C8	118.4 (2)
C4—C3—H3	120.4	C12—C13—H13	120.8
C5—C4—C3	121.08 (19)	C8—C13—H13	120.8
N1i—Cu1—O1—C1	163.78 (17)	C4—C5—C6—C7	177.20 (19)
N1—Cu1—O1—C1	−16.22 (17)	O1—C1—C6—C5	−179.35 (19)
O1—Cu1—N1—C7	11.64 (18)	C2—C1—C6—C5	0.6 (3)
O1i—Cu1—N1—C7	−168.36 (18)	O1—C1—C6—C7	3.4 (3)
O1—Cu1—N1—N2	−164.50 (14)	C2—C1—C6—C7	−176.57 (19)
O1i—Cu1—N1—N2	15.50 (14)	N2—N1—C7—C6	173.81 (18)
C7—N1—N2—S1	−84.65 (18)	Cu1—N1—C7—C6	−2.5 (3)
Cu1—N1—N2—S1	91.96 (14)	C5—C6—C7—N1	174.74 (19)
O3—S1—N2—N1	−169.59 (13)	C1—C6—C7—N1	−7.9 (3)
O2—S1—N2—N1	61.73 (15)	O3—S1—C8—C9	−169.03 (17)
C8—S1—N2—N1	−53.47 (15)	O2—S1—C8—C9	−33.7 (2)
Cu1—O1—C1—C6	11.6 (3)	N2—S1—C8—C9	79.30 (19)
Cu1—O1—C1—C2	−168.43 (14)	O3—S1—C8—C13	17.7 (2)
O1—C1—C2—C3	179.09 (19)	O2—S1—C8—C13	153.05 (17)
C6—C1—C2—C3	−0.9 (3)	N2—S1—C8—C13	−93.98 (19)
O1—C1—C2—Br1	0.9 (3)	C13—C8—C9—C10	0.9 (3)
C6—C1—C2—Br1	−179.07 (14)	S1—C8—C9—C10	−172.22 (17)
C1—C2—C3—C4	0.7 (3)	C8—C9—C10—C11	−0.1 (3)
Br1—C2—C3—C4	178.82 (15)	C9—C10—C11—C12	−1.1 (3)
C2—C3—C4—C5	−0.2 (3)	C10—C11—C12—C13	1.4 (4)
C2—C3—C4—Cl1	179.83 (16)	C11—C12—C13—C8	−0.5 (4)
C3—C4—C5—C6	−0.1 (3)	C9—C8—C13—C12	−0.6 (3)
Cl1—C4—C5—C6	179.93 (15)	S1—C8—C13—C12	172.46 (18)
C4—C5—C6—C1	−0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1i	0.88 (1)	2.07 (2)	2.722 (2)	130 (2)

Cu1—O1	1.905 (1)
Cu1—N1	1.963 (2)

O1—Cu1—N1	91.28 (6)
O1—Cu1—N1i	88.72 (6)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1i	0.88 (1)	2.07 (2)	2.722 (2)	130 (2)

Symmetry code: (i) .