Bis{μ-N′-[1-(5-bromo-2-oxidophen­yl)ethyl­idene]benzene­sulfono­hydrazidato}-κ3
               O
               2,N′:N;κ3
               N:O
               2,N′-bis­[(dimethyl sulfoxide-κO)copper(II)]

doi:10.1107/S1600536808002201

supplementary crystallographic information

Experimental

The Schiff base ligand was synthesized by refluxing 5-bromo-2-hydroxyacetophenone (0.6 g, 2.8 mmol) with benzene sulfonohydrazide (0.48 g,2.8 mmol)in ethanol for 2 h. The ligand then was refluxed with Copper (II) acetate for 5 h. The brown crystal were obtained by recrystalization the product from DMSO.

Figures

Fig. 1.

The molecular structure with displacement ellipsoids drawn at the 50% probability level, and H atoms shown as spheres of arbitrary radii [symmetry code: (i) -x + 2, -y + 1, -z].

Crystal data

[Cu₂(C₁₅H₁₁BrN₂O₃S)₂(C₂H₆OS)₂]	Z = 1
M_r = 1017.77	F(000) = 510
Triclinic, P1	D_x = 1.778 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0831 (1) Å	Cell parameters from 7546 reflections
b = 10.4972 (2) Å	θ = 2.7–31.0°
c = 12.9481 (2) Å	µ = 3.49 mm⁻¹
α = 68.157 (1)°	T = 123 K
β = 74.928 (1)°	Block, green
γ = 70.691 (1)°	0.40 × 0.31 × 0.20 mm
V = 950.56 (3) Å³

Data collection

Bruker APEXII diffractometer	4318 independent reflections
Radiation source: medium-focus sealed tube	3788 reflections with I > 2σ(I)
Graphite	R_int = 0.027
and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.335, T_max = 0.542	k = −13→13
12330 measured reflections	l = −16→16

Refinement

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.21	w = 1/[σ²(F_o²) + (0.0827P)² + 1.8365P] where P = (F_o² + 2F_c²)/3
4318 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 1.75 e Å⁻³
0 restraints	Δρ_min = −0.89 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

	x	y	z	U_iso*/U_eq
Br1	0.33316 (6)	0.23924 (5)	0.54963 (4)	0.03789 (17)
Cu1	1.09563 (6)	0.32031 (5)	0.10740 (4)	0.02020 (15)
S1	1.13219 (13)	0.63204 (10)	0.05283 (8)	0.0213 (2)
S2	1.41379 (13)	0.06832 (10)	0.18255 (8)	0.0230 (2)
O1	1.0528 (4)	0.2167 (3)	0.2622 (3)	0.0285 (6)
O2	1.2628 (4)	0.4956 (3)	0.0677 (3)	0.0278 (6)
O3	1.1615 (4)	0.7489 (3)	−0.0472 (3)	0.0292 (7)
O4	1.3150 (4)	0.1704 (3)	0.0840 (2)	0.0253 (6)
N1	0.9142 (4)	0.4879 (3)	0.1354 (3)	0.0195 (6)
N2	0.9352 (4)	0.6205 (3)	0.0558 (3)	0.0198 (6)
C1	0.8917 (5)	0.2298 (4)	0.3191 (3)	0.0219 (8)
C2	0.8558 (6)	0.1098 (5)	0.4082 (3)	0.0269 (9)
H2	0.9472	0.0236	0.4212	0.032*
C3	0.6946 (6)	0.1120 (5)	0.4770 (3)	0.0274 (9)
H3	0.6759	0.0294	0.5370	0.033*
C4	0.5591 (6)	0.2368 (5)	0.4575 (3)	0.0249 (8)
C5	0.5843 (5)	0.3557 (4)	0.3695 (4)	0.0243 (8)
H5	0.4889	0.4393	0.3569	0.029*
C6	0.7481 (5)	0.3565 (4)	0.2975 (3)	0.0208 (7)
C7	0.7691 (5)	0.4889 (4)	0.2075 (3)	0.0217 (8)
C8	0.6221 (7)	0.6230 (5)	0.1999 (5)	0.0392 (12)
H8A	0.6631	0.7033	0.1428	0.059*
H8B	0.5875	0.6396	0.2731	0.059*
H8C	0.5198	0.6135	0.1788	0.059*
C10	1.1190 (5)	0.6831 (4)	0.1713 (3)	0.0220 (8)
C11	1.1381 (6)	0.5793 (5)	0.2752 (4)	0.0269 (8)
H11	1.1558	0.4822	0.2833	0.032*
C12	1.1307 (6)	0.6200 (5)	0.3673 (4)	0.0318 (9)
H12	1.1418	0.5505	0.4393	0.038*
C13	1.1072 (6)	0.7618 (5)	0.3547 (4)	0.0327 (10)
H13	1.1064	0.7884	0.4174	0.039*
C14	1.0849 (6)	0.8649 (5)	0.2507 (4)	0.0304 (9)
H14	1.0656	0.9622	0.2429	0.036*
C15	1.0910 (6)	0.8258 (4)	0.1583 (4)	0.0249 (8)
H15	1.0761	0.8957	0.0869	0.030*
C16	1.6285 (6)	0.0005 (5)	0.1132 (4)	0.0294 (9)
H16A	1.6190	−0.0542	0.0690	0.044*
H16B	1.7060	−0.0613	0.1694	0.044*
H16C	1.6786	0.0797	0.0631	0.044*
C17	1.4719 (6)	0.1775 (5)	0.2371 (4)	0.0310 (9)
H17A	1.3669	0.2215	0.2823	0.046*
H17B	1.5168	0.2519	0.1746	0.046*
H17C	1.5640	0.1193	0.2844	0.046*

Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0284 (3)	0.0359 (3)	0.0357 (3)	−0.01063 (19)	0.00829 (19)	−0.0030 (2)
Cu1	0.0171 (3)	0.0210 (3)	0.0222 (3)	−0.00342 (18)	−0.00075 (18)	−0.00929 (19)
S1	0.0190 (5)	0.0249 (5)	0.0240 (5)	−0.0098 (4)	0.0014 (3)	−0.0118 (4)
S2	0.0192 (5)	0.0238 (5)	0.0253 (5)	−0.0066 (4)	−0.0020 (4)	−0.0070 (4)
O1	0.0205 (14)	0.0309 (15)	0.0248 (14)	0.0000 (12)	−0.0005 (11)	−0.0063 (12)
O2	0.0179 (14)	0.0312 (16)	0.0391 (17)	−0.0064 (12)	0.0007 (12)	−0.0200 (13)
O3	0.0320 (17)	0.0352 (16)	0.0255 (15)	−0.0200 (14)	0.0015 (13)	−0.0095 (13)
O4	0.0220 (14)	0.0278 (14)	0.0245 (14)	0.0011 (11)	−0.0040 (11)	−0.0130 (12)
N1	0.0206 (16)	0.0187 (15)	0.0205 (15)	−0.0074 (12)	−0.0020 (12)	−0.0063 (12)
N2	0.0201 (16)	0.0205 (15)	0.0214 (15)	−0.0094 (12)	−0.0014 (12)	−0.0074 (12)
C1	0.0202 (18)	0.0271 (19)	0.0204 (18)	−0.0047 (15)	−0.0025 (14)	−0.0113 (15)
C2	0.030 (2)	0.0246 (19)	0.0213 (19)	0.0012 (16)	−0.0058 (16)	−0.0085 (15)
C3	0.036 (2)	0.0252 (19)	0.0199 (18)	−0.0089 (17)	−0.0040 (17)	−0.0047 (15)
C4	0.024 (2)	0.029 (2)	0.0213 (18)	−0.0088 (16)	0.0002 (15)	−0.0081 (16)
C5	0.0196 (18)	0.0247 (19)	0.028 (2)	−0.0055 (15)	−0.0014 (15)	−0.0090 (16)
C6	0.0190 (18)	0.0193 (17)	0.0245 (18)	−0.0061 (14)	−0.0008 (15)	−0.0081 (14)
C7	0.0190 (18)	0.0202 (18)	0.0255 (19)	−0.0070 (14)	0.0012 (15)	−0.0084 (15)
C8	0.030 (2)	0.021 (2)	0.046 (3)	−0.0012 (18)	0.011 (2)	−0.0033 (19)
C10	0.0177 (18)	0.0252 (19)	0.0275 (19)	−0.0056 (15)	−0.0009 (15)	−0.0149 (16)
C11	0.025 (2)	0.026 (2)	0.029 (2)	−0.0045 (16)	−0.0016 (16)	−0.0115 (16)
C12	0.029 (2)	0.038 (2)	0.027 (2)	−0.0038 (19)	−0.0042 (17)	−0.0122 (18)
C13	0.030 (2)	0.044 (3)	0.032 (2)	−0.0112 (19)	−0.0001 (18)	−0.023 (2)
C14	0.030 (2)	0.030 (2)	0.037 (2)	−0.0118 (18)	0.0038 (18)	−0.0194 (19)
C15	0.024 (2)	0.0241 (19)	0.027 (2)	−0.0099 (16)	0.0023 (16)	−0.0099 (16)
C16	0.023 (2)	0.027 (2)	0.038 (2)	−0.0021 (16)	−0.0020 (17)	−0.0153 (18)
C17	0.031 (2)	0.038 (2)	0.031 (2)	−0.0086 (19)	−0.0062 (18)	−0.0181 (19)

Geometric parameters (Å, °)

Br1—C4	1.902 (4)	C5—H5	0.9500
Cu1—O1	1.894 (3)	C6—C7	1.472 (5)
Cu1—O4	1.986 (3)	C7—C8	1.501 (6)
Cu1—N1	1.967 (3)	C8—H8A	0.9800
Cu1—N2ⁱ	2.026 (3)	C8—H8B	0.9800
S1—O3	1.445 (3)	C8—H8C	0.9800
S1—O2	1.450 (3)	C10—C11	1.388 (6)
S1—N2	1.626 (3)	C10—C15	1.390 (6)
S1—C10	1.772 (4)	C11—C12	1.391 (6)
S2—O4	1.537 (3)	C11—H11	0.9500
S2—C17	1.779 (4)	C12—C13	1.387 (7)
S2—C16	1.781 (4)	C12—H12	0.9500
O1—C1	1.310 (5)	C13—C14	1.389 (7)
N1—C7	1.295 (5)	C13—H13	0.9500
N1—N2	1.423 (4)	C14—C15	1.388 (6)
N2—Cu1ⁱ	2.026 (3)	C14—H14	0.9500
C1—C2	1.410 (6)	C15—H15	0.9500
C1—C6	1.438 (5)	C16—H16A	0.9800
C2—C3	1.372 (6)	C16—H16B	0.9800
C2—H2	0.9500	C16—H16C	0.9800
C3—C4	1.388 (6)	C17—H17A	0.9800
C3—H3	0.9500	C17—H17B	0.9800
C4—C5	1.374 (6)	C17—H17C	0.9800
C5—C6	1.407 (6)

O1—Cu1—N1	89.77 (13)	C1—C6—C7	122.5 (4)
O1—Cu1—O4	91.02 (13)	N1—C7—C6	119.4 (3)
N1—Cu1—O4	167.44 (13)	N1—C7—C8	120.8 (4)
O1—Cu1—N2ⁱ	153.28 (14)	C6—C7—C8	119.7 (4)
N1—Cu1—N2ⁱ	93.89 (13)	C7—C8—H8A	109.5
O4—Cu1—N2ⁱ	91.03 (13)	C7—C8—H8B	109.5
O3—S1—O2	118.67 (19)	H8A—C8—H8B	109.5
O3—S1—N2	105.18 (18)	C7—C8—H8C	109.5
O2—S1—N2	112.07 (17)	H8A—C8—H8C	109.5
O3—S1—C10	107.86 (19)	H8B—C8—H8C	109.5
O2—S1—C10	106.05 (19)	C11—C10—C15	121.3 (4)
N2—S1—C10	106.37 (18)	C11—C10—S1	119.2 (3)
O4—S2—C17	105.9 (2)	C15—C10—S1	119.5 (3)
O4—S2—C16	102.9 (2)	C10—C11—C12	118.8 (4)
C17—S2—C16	98.1 (2)	C10—C11—H11	120.6
C1—O1—Cu1	121.3 (3)	C12—C11—H11	120.6
S2—O4—Cu1	120.97 (17)	C13—C12—C11	120.3 (4)
C7—N1—N2	117.5 (3)	C13—C12—H12	119.8
C7—N1—Cu1	127.0 (3)	C11—C12—H12	119.8
N2—N1—Cu1	114.7 (2)	C12—C13—C14	120.3 (4)
N1—N2—S1	108.2 (2)	C12—C13—H13	119.9
N1—N2—Cu1ⁱ	122.8 (2)	C14—C13—H13	119.9
S1—N2—Cu1ⁱ	105.85 (17)	C15—C14—C13	119.9 (4)
O1—C1—C2	117.5 (4)	C15—C14—H14	120.0
O1—C1—C6	125.2 (4)	C13—C14—H14	120.0
C2—C1—C6	117.3 (4)	C14—C15—C10	119.3 (4)
C3—C2—C1	122.9 (4)	C14—C15—H15	120.4
C3—C2—H2	118.5	C10—C15—H15	120.4
C1—C2—H2	118.5	S2—C16—H16A	109.5
C2—C3—C4	119.0 (4)	S2—C16—H16B	109.5
C2—C3—H3	120.5	H16A—C16—H16B	109.5
C4—C3—H3	120.5	S2—C16—H16C	109.5
C5—C4—C3	120.7 (4)	H16A—C16—H16C	109.5
C5—C4—Br1	119.9 (3)	H16B—C16—H16C	109.5
C3—C4—Br1	119.3 (3)	S2—C17—H17A	109.5
C4—C5—C6	121.5 (4)	S2—C17—H17B	109.5
C4—C5—H5	119.2	H17A—C17—H17B	109.5
C6—C5—H5	119.2	S2—C17—H17C	109.5
C5—C6—C1	118.4 (4)	H17A—C17—H17C	109.5
C5—C6—C7	119.0 (4)	H17B—C17—H17C	109.5

N1—Cu1—O1—C1	40.0 (3)	C3—C4—C5—C6	−1.3 (7)
O4—Cu1—O1—C1	−152.5 (3)	Br1—C4—C5—C6	−178.1 (3)
N2ⁱ—Cu1—O1—C1	−58.2 (5)	C4—C5—C6—C1	−1.1 (6)
C17—S2—O4—Cu1	−58.7 (3)	C4—C5—C6—C7	−177.5 (4)
C16—S2—O4—Cu1	−161.2 (2)	O1—C1—C6—C5	−177.2 (4)
O1—Cu1—O4—S2	−23.1 (2)	C2—C1—C6—C5	3.2 (6)
N1—Cu1—O4—S2	70.5 (7)	O1—C1—C6—C7	−0.9 (6)
N2ⁱ—Cu1—O4—S2	−176.4 (2)	C2—C1—C6—C7	179.6 (4)
O1—Cu1—N1—C7	−34.4 (4)	N2—N1—C7—C6	−174.7 (3)
O4—Cu1—N1—C7	−128.1 (6)	Cu1—N1—C7—C6	15.4 (5)
N2ⁱ—Cu1—N1—C7	119.1 (3)	N2—N1—C7—C8	5.6 (6)
O1—Cu1—N1—N2	155.5 (3)	Cu1—N1—C7—C8	−164.3 (4)
O4—Cu1—N1—N2	61.8 (7)	C5—C6—C7—N1	−174.6 (4)
N2ⁱ—Cu1—N1—N2	−51.0 (3)	C1—C6—C7—N1	9.1 (6)
C7—N1—N2—S1	132.6 (3)	C5—C6—C7—C8	5.1 (6)
Cu1—N1—N2—S1	−56.4 (3)	C1—C6—C7—C8	−171.2 (4)
C7—N1—N2—Cu1ⁱ	−103.8 (4)	O3—S1—C10—C11	−163.2 (3)
Cu1—N1—N2—Cu1ⁱ	67.3 (3)	O2—S1—C10—C11	−35.1 (4)
O3—S1—N2—N1	166.0 (2)	N2—S1—C10—C11	84.4 (4)
O2—S1—N2—N1	35.8 (3)	O3—S1—C10—C15	16.4 (4)
C10—S1—N2—N1	−79.7 (3)	O2—S1—C10—C15	144.5 (3)
O3—S1—N2—Cu1ⁱ	32.7 (2)	N2—S1—C10—C15	−96.0 (3)
O2—S1—N2—Cu1ⁱ	−97.6 (2)	C15—C10—C11—C12	−0.7 (6)
C10—S1—N2—Cu1ⁱ	146.95 (18)	S1—C10—C11—C12	178.8 (3)
Cu1—O1—C1—C2	148.7 (3)	C10—C11—C12—C13	−0.9 (7)
Cu1—O1—C1—C6	−30.8 (5)	C11—C12—C13—C14	2.1 (7)
O1—C1—C2—C3	177.1 (4)	C12—C13—C14—C15	−1.7 (7)
C6—C1—C2—C3	−3.3 (6)	C13—C14—C15—C10	0.1 (7)
C1—C2—C3—C4	1.1 (7)	C11—C10—C15—C14	1.1 (6)
C2—C3—C4—C5	1.3 (7)	S1—C10—C15—C14	−178.5 (3)
C2—C3—C4—Br1	178.2 (3)

Symmetry codes: (i) −x+2, −y+1, −z.

Formats:

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