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In the centrosymmetric title compound, [Cu2(C9H7Br2NO4S)2(CH3OH)2], each CuII atom adopts a distorted square-pyramidal CuO4N coordination geometry, formed by one N atom and three O atoms from two different 2-[(E)-(3,5-dibromo-2-oxidophen­yl)­methyl­eneamino]ethanesulfonate ligands and one O atom from a methanol mol­ecule. Adjacent CuII atoms are linked by bridging sulfonate groups to form a dinuclear compound, with a Cu...Cu distance of 5.41 (1) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015905/bi2166sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015905/bi2166Isup2.hkl
Contains datablock I

CCDC reference: 606334

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.016 Å
  • R factor = 0.071
  • wR factor = 0.209
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 16
Alert level C PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Bis{2-[(E)-(3,5-dibromo-2-oxidophenyl)methyleneamino]ethanesulfonato- κ3N,O·O':O''}bis[methanolcopper(II)] top
Crystal data top
[Cu2(C9H7Br2NO4S)2(CH4O)2]Z = 1
Mr = 961.24F(000) = 466
Triclinic, P1Dx = 2.271 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.280 (1) ÅCell parameters from 182 reflections
b = 9.374 (2) Åθ = 2.6–25.0°
c = 14.785 (3) ŵ = 7.40 mm1
α = 87.97 (3)°T = 293 K
β = 88.26 (3)°Prism, blue
γ = 74.02 (3)°0.28 × 0.22 × 0.20 mm
V = 702.8 (2) Å3
Data collection top
Bruker SMART CCD
diffractometer
2473 independent reflections
Radiation source: fine-focus sealed tube1583 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 66
Tmin = 0.122, Tmax = 0.228k = 1011
3971 measured reflectionsl = 179
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.209H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1257P)2]
where P = (Fo2 + 2Fc2)/3
2473 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 1.63 e Å3
6 restraintsΔρmin = 1.24 e Å3
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
xyzUiso*/Ueq
Br10.6146 (3)1.03091 (14)0.33139 (10)0.0514 (5)
Br20.0076 (2)0.72579 (14)0.53216 (9)0.0440 (4)
C10.640 (2)0.7293 (12)0.3043 (8)0.029 (3)
C20.511 (2)0.8550 (12)0.3539 (8)0.032 (3)
C30.325 (2)0.8562 (12)0.4211 (8)0.032 (3)
H30.24850.94220.45240.038*
C40.254 (2)0.7257 (13)0.4415 (8)0.033 (3)
C50.366 (2)0.5985 (13)0.3936 (8)0.035 (3)
H50.31400.51260.40610.042*
C60.560 (2)0.6001 (12)0.3254 (8)0.029 (3)
C70.672 (2)0.4612 (12)0.2794 (8)0.027 (3)
H70.60360.38240.29640.033*
C80.931 (2)0.2838 (11)0.1824 (7)0.027 (3)
H8A0.79400.23540.19740.033*
H8B1.09200.22650.21060.033*
C90.9724 (19)0.2881 (12)0.0822 (8)0.028 (3)
H9A0.83610.36890.05580.033*
H9B0.95780.19610.05770.033*
C101.164 (3)0.8851 (12)0.1369 (10)0.045 (3)
H10A1.04590.93040.08930.068*
H10B1.32180.91650.13070.068*
H10C1.08000.91430.19440.068*
Cu11.0223 (2)0.58622 (13)0.17155 (9)0.0264 (4)
N10.8534 (17)0.4361 (9)0.2181 (6)0.027 (2)
O10.8188 (15)0.7362 (8)0.2442 (5)0.0324 (19)
O21.3002 (14)0.4409 (8)0.1045 (6)0.035 (2)
O31.2841 (14)0.3481 (8)0.0445 (5)0.0318 (18)
O41.4800 (15)0.1801 (8)0.0767 (6)0.036 (2)
O51.2290 (14)0.7240 (7)0.1310 (5)0.033 (2)
H5A1.28190.72580.07830.050*
S11.2836 (5)0.3124 (3)0.0525 (2)0.0248 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0671 (9)0.0318 (7)0.0594 (10)0.0221 (6)0.0286 (8)0.0134 (7)
Br20.0443 (8)0.0442 (8)0.0421 (8)0.0117 (6)0.0224 (6)0.0044 (6)
C10.040 (7)0.029 (6)0.021 (6)0.014 (5)0.005 (5)0.004 (5)
C20.038 (6)0.025 (6)0.035 (7)0.012 (5)0.006 (6)0.003 (6)
C30.038 (6)0.023 (6)0.028 (7)0.001 (5)0.006 (5)0.002 (5)
C40.027 (6)0.039 (6)0.031 (7)0.007 (5)0.017 (5)0.007 (6)
C50.043 (7)0.028 (6)0.037 (7)0.012 (5)0.011 (6)0.006 (6)
C60.024 (5)0.026 (6)0.038 (7)0.010 (4)0.009 (5)0.001 (5)
C70.025 (6)0.025 (5)0.032 (7)0.009 (4)0.001 (5)0.002 (5)
C80.037 (6)0.020 (5)0.029 (6)0.015 (5)0.011 (5)0.009 (5)
C90.024 (5)0.025 (5)0.037 (7)0.013 (4)0.006 (5)0.010 (5)
C100.051 (6)0.029 (5)0.056 (7)0.012 (5)0.010 (6)0.000 (6)
Cu10.0288 (7)0.0225 (7)0.0304 (8)0.0118 (6)0.0102 (6)0.0063 (6)
N10.029 (5)0.021 (4)0.029 (5)0.005 (4)0.011 (4)0.008 (4)
O10.042 (4)0.026 (4)0.033 (5)0.018 (3)0.017 (4)0.009 (4)
O20.029 (4)0.027 (4)0.057 (6)0.020 (3)0.018 (4)0.021 (4)
O30.032 (4)0.032 (4)0.032 (4)0.010 (3)0.008 (4)0.002 (4)
O40.037 (4)0.034 (4)0.040 (5)0.013 (4)0.002 (4)0.000 (4)
O50.036 (4)0.025 (4)0.041 (5)0.013 (3)0.024 (4)0.010 (4)
S10.0226 (13)0.0210 (13)0.0323 (16)0.0088 (11)0.0070 (12)0.0042 (12)
Geometric parameters (Å, º) top
Br1—C21.891 (11)C8—H8B0.970
Br2—C41.894 (11)C9—S11.761 (10)
C1—O11.289 (12)C9—H9A0.970
C1—C21.407 (16)C9—H9B0.970
C1—C61.412 (14)C10—O51.459 (13)
C2—C31.372 (15)C10—H10A0.960
C3—C41.396 (15)C10—H10B0.960
C3—H30.930C10—H10C0.960
C4—C51.385 (16)Cu1—O11.868 (7)
C5—C61.418 (15)Cu1—N11.959 (9)
C5—H50.930Cu1—O21.974 (7)
C6—C71.456 (15)Cu1—O51.974 (7)
C7—N11.279 (13)Cu1—O3i2.466 (4)
C7—H70.930O2—S11.476 (8)
C8—N11.484 (13)O3—S11.460 (8)
C8—C91.491 (15)O4—S11.423 (8)
C8—H8A0.970O5—H5A0.821
O1—C1—C2120.5 (10)C8—C9—S1111.6 (8)
O1—C1—C6124.1 (10)C8—C9—H9A109.3
C2—C1—C6115.4 (10)S1—C9—H9A109.3
C3—C2—C1124.3 (10)C8—C9—H9B109.3
C3—C2—Br1117.7 (9)S1—C9—H9B109.3
C1—C2—Br1117.8 (8)H9A—C9—H9B108.0
C2—C3—C4118.8 (10)O1—Cu1—N194.4 (3)
C2—C3—H3120.6O1—Cu1—O2167.9 (3)
C4—C3—H3120.6N1—Cu1—O293.5 (3)
C5—C4—C3120.4 (10)O1—Cu1—O588.2 (3)
C5—C4—Br2120.1 (9)N1—Cu1—O5173.6 (3)
C3—C4—Br2119.5 (9)O2—Cu1—O583.0 (3)
C4—C5—C6119.6 (11)C7—N1—C8115.8 (9)
C4—C5—H5120.2C7—N1—Cu1123.4 (7)
C6—C5—H5120.2C8—N1—Cu1120.7 (6)
C1—C6—C5121.5 (11)C1—O1—Cu1128.9 (7)
C1—C6—C7122.3 (10)S1—O2—Cu1129.9 (4)
C5—C6—C7116.3 (9)C10—O5—Cu1129.5 (7)
N1—C7—C6126.9 (10)C10—O5—H5A92.7
N1—C7—H7116.5Cu1—O5—H5A120.9
C6—C7—H7116.5O4—S1—O3112.9 (5)
N1—C8—C9110.8 (8)O4—S1—O2112.6 (5)
N1—C8—H8A109.5O3—S1—O2110.3 (5)
C9—C8—H8A109.5O4—S1—C9108.5 (5)
N1—C8—H8B109.5O3—S1—C9107.6 (5)
C9—C8—H8B109.5O2—S1—C9104.6 (5)
H8A—C8—H8B108.1
Symmetry code: (i) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O3ii0.822.252.758 (10)121
Symmetry code: (ii) x+3, y+1, z.
 

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