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The reaction of copper(II) chloride with 2-bromo-1,4-benzene­di­carboxyl­ic acid (H2bbdc) and 2,2′-bi­pyridine in aqueous solution under hydro­thermal conditions gave the title compound, [Cu(C8H4BrO4)2(C10H8N2)]. The CuII atom lies on a twofold axis and is coordinated by two singly deprotonated 2-bromo-1,4-benzene­di­carboxyl­ate groups and one 2,2′-bi­pyridine ligand in a square-planar geometry. Intermolecular O—H...O hydrogen bonds between carboxyl­ate groups ensure a two-dimensional architecture with double sheets.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803014806/ob6268sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803014806/ob6268Isup2.hkl
Contains datablock I

CCDC reference: 221622

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.057
  • wR factor = 0.134
  • Data-to-parameter ratio = 15.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
CRYSC_01 Alert C The word below has not been recognised as a standard identifier. deep
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
[Cu(C8H4BrO4)2(C10H8N2)]F(000) = 1396
Mr = 707.77Dx = 1.831 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2ycCell parameters from 2917 reflections
a = 12.0675 (12) Åθ = 2.2–27.4°
b = 15.2713 (16) ŵ = 4.02 mm1
c = 14.4430 (15) ÅT = 296 K
β = 105.325 (11)°Block, deep blue
V = 2567.0 (5) Å30.29 × 0.21 × 0.11 mm
Z = 4
Data collection top
Rigaku RAXIS-RAPID
diffractometer
2917 independent reflections
Radiation source: fine-focus sealed tube2127 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
Detector resolution: 10.00 pixels mm-1θmax = 27.4°, θmin = 2.2°
ω scansh = 1515
Absorption correction: multi-scan
ABSCOR (Higashi, 1995)
k = 1919
Tmin = 0.315, Tmax = 0.647l = 1818
10701 measured reflections
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0435P)2 + 15.099P]
where P = (Fo2 + 2Fc2)/3
2917 reflections(Δ/σ)max = 0.002
186 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = 0.56 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*/UeqOcc. (<1)
Cu10.50000.26514 (5)0.25000.0331 (2)
Br10.12831 (5)0.12190 (4)0.07584 (6)0.0516 (2)0.90
Br20.4646 (13)0.2244 (5)0.1569 (10)0.123 (4)0.10
O10.3899 (3)0.1751 (2)0.1913 (3)0.0452 (10)
O20.4827 (4)0.1314 (3)0.0854 (3)0.0615 (13)
O30.2588 (4)0.2869 (3)0.1132 (4)0.0712 (14)
O40.0884 (3)0.2214 (2)0.0892 (3)0.0522 (11)
N10.6057 (3)0.3627 (2)0.2998 (3)0.0320 (9)
C10.3475 (4)0.0352 (3)0.1210 (4)0.0332 (11)
C20.2299 (4)0.0256 (3)0.1015 (4)0.0346 (11)
H20.18330.07500.09360.042*0.10
C30.1802 (4)0.0576 (3)0.0936 (4)0.0345 (11)
H30.10080.06350.07850.041*
C40.2490 (4)0.1305 (3)0.1081 (4)0.0362 (12)
C50.3676 (5)0.1219 (3)0.1270 (5)0.0454 (14)
H50.41470.17110.13600.054*0.90
C60.4141 (5)0.0388 (3)0.1322 (5)0.0472 (15)
H60.49330.03290.14370.057*
C70.4100 (4)0.1222 (3)0.1313 (4)0.0388 (12)
C80.2011 (5)0.2212 (3)0.1040 (4)0.0435 (13)
C90.5608 (4)0.4432 (3)0.2794 (4)0.0322 (11)
C100.6256 (5)0.5173 (3)0.3106 (4)0.0445 (13)
H100.59290.57260.29710.053*
C110.7388 (5)0.5087 (4)0.3619 (4)0.0470 (14)
H110.78380.55810.38240.056*
C120.7849 (5)0.4256 (4)0.3825 (4)0.0432 (13)
H120.86110.41810.41690.052*
C130.7158 (5)0.3554 (3)0.3511 (4)0.0397 (12)
H130.74620.29960.36580.048*
H40.05790.26900.08100.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0303 (4)0.0144 (4)0.0501 (6)0.0000.0029 (4)0.000
Br10.0385 (3)0.0304 (3)0.0820 (5)0.0015 (2)0.0088 (3)0.0050 (3)
Br20.187 (12)0.038 (4)0.159 (10)0.001 (6)0.072 (10)0.003 (5)
O10.0342 (19)0.0212 (18)0.077 (3)0.0050 (14)0.0092 (19)0.0109 (18)
O20.068 (3)0.047 (3)0.077 (3)0.040 (2)0.032 (3)0.014 (2)
O30.071 (3)0.022 (2)0.124 (4)0.002 (2)0.033 (3)0.007 (2)
O40.048 (2)0.029 (2)0.083 (3)0.0185 (17)0.023 (2)0.0069 (19)
N10.031 (2)0.023 (2)0.042 (2)0.0011 (16)0.0098 (19)0.0018 (17)
C10.032 (2)0.020 (2)0.049 (3)0.0101 (18)0.013 (2)0.003 (2)
C20.036 (3)0.024 (2)0.045 (3)0.007 (2)0.014 (2)0.002 (2)
C30.032 (2)0.028 (3)0.046 (3)0.011 (2)0.015 (2)0.004 (2)
C40.040 (3)0.022 (2)0.049 (3)0.011 (2)0.015 (2)0.006 (2)
C50.041 (3)0.021 (2)0.078 (4)0.002 (2)0.023 (3)0.001 (3)
C60.032 (3)0.027 (3)0.083 (4)0.009 (2)0.015 (3)0.006 (3)
C70.036 (3)0.021 (2)0.055 (3)0.009 (2)0.002 (3)0.001 (2)
C80.054 (3)0.028 (3)0.052 (3)0.009 (2)0.021 (3)0.004 (2)
C90.040 (3)0.021 (2)0.038 (3)0.0020 (19)0.016 (2)0.000 (2)
C100.058 (3)0.023 (3)0.056 (3)0.005 (2)0.021 (3)0.006 (2)
C110.053 (3)0.034 (3)0.054 (3)0.015 (3)0.013 (3)0.011 (3)
C120.035 (3)0.047 (3)0.048 (3)0.008 (2)0.013 (3)0.003 (3)
C130.039 (3)0.028 (3)0.050 (3)0.002 (2)0.010 (3)0.001 (2)
Geometric parameters (Å, º) top
Cu1—O11.945 (3)C2—H20.9300
Cu1—O1i1.945 (3)C3—C41.371 (7)
Cu1—N11.970 (4)C3—H30.9300
Cu1—N1i1.970 (4)C4—C51.391 (7)
Br1—C21.887 (5)C4—C81.496 (6)
Br2—C51.934 (12)C5—C61.381 (7)
Br2—Br2i2.60 (3)C5—H50.9300
O1—C71.255 (6)C6—H60.9300
O2—C71.239 (7)C9—C101.381 (7)
O3—C81.208 (7)C9—C9i1.489 (10)
O4—C81.319 (7)C10—C111.378 (8)
O4—H40.809C10—H100.9300
N1—C91.344 (6)C11—C121.386 (8)
N1—C131.344 (7)C11—H110.9300
C1—C61.373 (7)C12—C131.361 (7)
C1—C21.379 (7)C12—H120.9300
C1—C71.516 (6)C13—H130.9300
C2—C31.397 (6)
O1—Cu1—O1i90.0 (2)C6—C5—H5120.7
O1—Cu1—N1175.07 (17)C4—C5—H5120.7
O1i—Cu1—N194.26 (16)C1—C6—C5122.2 (5)
O1—Cu1—N1i94.26 (16)C1—C6—H6118.9
O1i—Cu1—N1i175.07 (17)C5—C6—H6118.9
N1—Cu1—N1i81.6 (2)O2—C7—O1126.2 (5)
C5—Br2—Br2i104.2 (5)O2—C7—C1116.9 (5)
C7—O1—Cu1121.4 (3)O1—C7—C1116.7 (5)
C9—N1—C13118.6 (4)O3—C8—O4123.7 (5)
C9—N1—Cu1115.3 (3)O3—C8—C4124.0 (5)
C13—N1—Cu1126.1 (3)O4—C8—C4112.3 (5)
C6—C1—C2118.4 (4)N1—C9—C10121.2 (5)
C6—C1—C7116.7 (4)N1—C9—C9i113.8 (3)
C2—C1—C7124.9 (4)C10—C9—C9i125.0 (3)
C1—C2—C3120.6 (5)C11—C10—C9119.5 (5)
C1—C2—Br1122.5 (4)C11—C10—H10120.3
C3—C2—Br1116.8 (4)C9—C10—H10120.3
C1—C2—H2119.7C10—C11—C12119.2 (5)
C4—C3—C2119.8 (4)C10—C11—H11120.4
C4—C3—H3120.1C12—C11—H11120.4
C2—C3—H3120.1C13—C12—C11118.3 (5)
C3—C4—C5120.2 (4)C13—C12—H12120.8
C3—C4—C8122.3 (5)C11—C12—H12120.8
C5—C4—C8117.5 (5)N1—C13—C12123.2 (5)
C6—C5—C4118.7 (5)N1—C13—H13118.4
C6—C5—Br2121.2 (6)C12—C13—H13118.4
C4—C5—Br2119.9 (5)C8—O4—H4115.8
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O2ii0.811.782.578 (6)168
C11—H11···O3iii0.932.433.141 (8)134
C12—H12···O2iv0.932.603.368 (7)140
C13—H13···O1i0.922.513.028 (6)116
Symmetry codes: (i) x+1, y, z+1/2; (ii) x1/2, y1/2, z; (iii) x+1, y+1, z+1/2; (iv) x+1/2, y+1/2, z+1/2.
 

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