Bis(3-hydroxy­benzoato-κO)bis­(1H-imidazole-κN³)copper(II)

The metal atom in the title compound, [Cu(C₇H₅O₃)₂(C₃H₄N₂)₂], is coordinated by two O atoms (from two carboxyl­ate anions) and two N atoms (from two N-heterocycles) in a square-planar geometry; it occupies a special position of site symmetry . Above and below the square are the hydroxy O atoms of adjacent mol­ecules. This weak inter­action [2.646 (2) Å] leads to the formation of a linear chain; the chains are consolidated into a layer through hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.132
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.22
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O3   -H3O     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              N2   -H2N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O3   -H3O     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              N2   -H2N     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.76(3), Rep   1.760(10) ......       3.00 su-Ra
              H3O  -O2      1.555   1.556

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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

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Computing details

Data collection: APEX2 software (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: Difference Fourier synthesis, with Cu1 at (1/2, 1/2, 1/2); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2006).

(I)

Crystal data

[Cu(C7H5O3)2(C3H4N2)2]	F(000) = 486
Mr = 473.92	Dx = 1.573 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3090 reflections
a = 9.299 (1) Å	θ = 2.7–29.0°
b = 13.333 (1) Å	µ = 1.14 mm^−1
c = 8.078 (1) Å	T = 295 K
β = 92.196 (1)°	Block, blue
V = 1000.80 (18) Å^3	0.32 × 0.22 × 0.13 mm
Z = 2

Data collection

Bruker APEX2 area-detector diffractometer	2281 independent reflections
Radiation source: fine-focus sealed tube	1859 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.712, Tmax = 0.866	k = −10→17
6475 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0767P)^2 + 0.451P] where P = (Fo^2 + 2Fc^2)/3
2281 reflections	(Δ/σ)max = 0.001
150 parameters	Δρmax = 1.00 e Å^−3
2 restraints	Δρmin = −0.45 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cu1	0.5000	0.5000	0.5000	0.0278 (2)
O1	0.6093 (2)	0.5471 (1)	0.7003 (2)	0.0332 (4)
O2	0.8294 (2)	0.5635 (2)	0.6012 (2)	0.0518 (6)
O3	0.7265 (2)	0.5086 (2)	1.3120 (3)	0.0397 (5)
N1	0.5549 (2)	0.3608 (2)	0.5588 (3)	0.0310 (5)
N2	0.5375 (3)	0.2049 (2)	0.6409 (3)	0.0407 (6)
C1	0.7452 (3)	0.5632 (2)	0.7165 (3)	0.0303 (5)
C2	0.8028 (3)	0.5819 (2)	0.8897 (3)	0.0266 (5)
C3	0.7332 (3)	0.5418 (2)	1.0247 (3)	0.0277 (5)
C4	0.7913 (3)	0.5551 (2)	1.1839 (3)	0.0281 (5)
C5	0.9152 (3)	0.6114 (2)	1.2093 (3)	0.0392 (7)
C6	0.9825 (4)	0.6523 (3)	1.0748 (4)	0.0486 (8)
C7	0.9288 (3)	0.6365 (2)	0.9157 (3)	0.0394 (7)
C8	0.6895 (3)	0.3247 (2)	0.6034 (4)	0.0436 (7)
C9	0.6793 (3)	0.2285 (2)	0.6554 (4)	0.0449 (7)
C10	0.4670 (3)	0.2858 (2)	0.5827 (4)	0.0396 (6)
H3	0.6479	0.5061	1.0079	0.033*
H5	0.9531	0.6218	1.3161	0.047*
H6	1.0651	0.6908	1.0922	0.058*
H7	0.9767	0.6622	0.8262	0.047*
H8	0.7747	0.3610	0.5986	0.052*
H9	0.7541	0.1872	0.6933	0.054*
H10	0.3681	0.2885	0.5619	0.047*
H3o	0.770 (4)	0.525 (3)	1.402 (3)	0.06 (1)*
H2n	0.495 (4)	0.152 (2)	0.673 (5)	0.06 (1)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0357 (3)	0.0247 (3)	0.0220 (3)	0.0007 (2)	−0.0136 (2)	−0.0012 (2)
O1	0.038 (1)	0.036 (1)	0.024 (1)	0.003 (1)	−0.014 (1)	−0.006 (1)
O2	0.056 (1)	0.083 (2)	0.017 (1)	−0.014 (1)	0.000 (1)	−0.004 (1)
O3	0.043 (1)	0.056 (1)	0.020 (1)	−0.011 (1)	0.00 (1)	0.004 (1)
N1	0.037 (1)	0.028 (1)	0.027 (1)	0.001 (1)	−0.006 (1)	0.002 (1)
N2	0.046 (1)	0.031 (1)	0.045 (1)	−0.002 (1)	0.002 (1)	0.009 (1)
C1	0.041 (1)	0.031 (1)	0.019 (1)	−0.002 (1)	−0.007 (1)	−0.001 (1)
C2	0.031 (1)	0.032 (1)	0.016 (1)	0.001 (1)	−0.006 (1)	−0.001 (1)
C3	0.027 (1)	0.035 (1)	0.021 (1)	−0.005 (1)	−0.005 (1)	−0.002 (1)
C4	0.030 (1)	0.036 (1)	0.019 (1)	0.000 (1)	−0.002 (1)	−0.001 (1)
C5	0.041 (2)	0.058 (2)	0.018 (1)	−0.012 (1)	−0.008 (1)	−0.004 (1)
C6	0.044 (2)	0.072 (2)	0.030 (2)	−0.029 (2)	−0.006 (1)	−0.002 (1)
C7	0.041 (2)	0.056 (2)	0.021 (1)	−0.016 (1)	0.000 (1)	0.002 (1)
C8	0.036 (2)	0.038 (2)	0.056 (2)	−0.003 (1)	−0.013 (1)	0.007 (1)
C9	0.044 (2)	0.036 (2)	0.053 (2)	0.006 (1)	−0.012 (1)	0.009 (1)
C10	0.035 (1)	0.034 (1)	0.049 (2)	0.000 (1)	−0.004 (1)	0.006 (1)

Geometric parameters (Å, º)

Cu1—N1	1.978 (2)	C2—C3	1.396 (3)
Cu1—N1^i	1.978 (2)	C3—C4	1.387 (3)
Cu1—O1	1.980 (2)	C4—C5	1.384 (4)
Cu1—O1^i	1.980 (2)	C5—C6	1.386 (4)
Cu1—O3^ii	2.646 (2)	C6—C7	1.377 (4)
Cu1—O3^iii	2.646 (2)	C8—C9	1.354 (4)
O1—C1	1.284 (3)	O3—H3o	0.85 (1)
O2—C1	1.239 (3)	N2—H2n	0.85 (1)
O3—C4	1.366 (3)	C3—H3	0.93
N1—C10	1.310 (4)	C5—H5	0.93
N1—C8	1.376 (4)	C6—H6	0.93
N2—C10	1.338 (4)	C7—H7	0.93
N2—C9	1.357 (4)	C8—H8	0.93
C1—C2	1.500 (3)	C9—H9	0.93
C2—C7	1.388 (4)	C10—H10	0.93
N1—Cu1—N1^i	180	O3—C4—C5	121.5 (2)
N1—Cu1—O1	89.0 (1)	O3—C4—C3	118.5 (2)
N1—Cu1—O1^i	91.1 (1)	C5—C4—C3	119.9 (2)
N1—Cu1—O3^ii	88.52 (1)	C4—C5—C6	119.7 (2)
N1—Cu1—O3^iii	91.5 (1)	C7—C6—C5	120.8 (3)
N1^i—Cu1—O1	91.1 (1)	C6—C7—C2	119.7 (2)
N1^i—Cu1—O1^i	89.0 (1)	C9—C8—N1	109.8 (3)
O1—Cu1—O1^i	180	C8—C9—N2	105.8 (3)
N1^i—Cu1—O3^iii	88.52 (8)	N1—C10—N2	111.6 (3)
O1—Cu1—O3^iii	86.55 (7)	C4—O3—H3o	109 (3)
O1^i—Cu1—O3^iii	93.45 (7)	C10—N2—H2n	123 (3)
N1^i—Cu1—O3^ii	91.48 (8)	C9—N2—H2n	129 (3)
O1—Cu1—O3^ii	93.45 (7)	C4—C3—H3	120.0
O1^i—Cu1—O3^ii	86.55 (7)	C2—C3—H3	120.0
O3^iii—Cu1—O3^ii	180.0	C4—C5—H5	120.1
C1—O1—Cu1	127.5 (2)	C6—C5—H5	120.1
C10—N1—C8	105.1 (2)	C7—C6—H6	119.6
C10—N1—Cu1	126.5 (2)	C5—C6—H6	119.6
C8—N1—Cu1	127.9 (2)	C6—C7—H7	120.1
C10—N2—C9	107.7 (2)	C2—C7—H7	120.1
O2—C1—O1	124.9 (2)	C9—C8—H8	125.1
O2—C1—C2	119.1 (2)	N1—C8—H8	125.1
O1—C1—C2	115.9 (2)	C8—C9—H9	127.1
C7—C2—C3	119.7 (2)	N2—C9—H9	127.1
C7—C2—C1	119.9 (2)	N1—C10—H10	124.2
C3—C2—C1	120.4 (2)	N2—C10—H10	124.2
C4—C3—C2	120.0 (2)
N1^i—Cu1—O1—C1	−97.3 (2)	C7—C2—C3—C4	−1.0 (4)
N1—Cu1—O1—C1	82.7 (2)	C1—C2—C3—C4	176.7 (2)
O3^iii—Cu1—O1—C1	174.3 (2)	C2—C3—C4—O3	−175.1 (2)
O3^ii—Cu1—O1—C1	−5.7 (2)	C2—C3—C4—C5	2.4 (4)
O1—Cu1—N1—C10	122.8 (3)	O3—C4—C5—C6	176.0 (3)
O1^i—Cu1—N1—C10	−57.2 (3)	C3—C4—C5—C6	−1.5 (4)
O3^iii—Cu1—N1—C10	36.3 (3)	C4—C5—C6—C7	−0.9 (5)
O3^ii—Cu1—N1—C10	−143.7 (3)	C5—C6—C7—C2	2.3 (5)
O1—Cu1—N1—C8	−48.2 (3)	C3—C2—C7—C6	−1.3 (4)
O1^i—Cu1—N1—C8	131.8 (3)	C1—C2—C7—C6	−179.0 (3)
O3^iii—Cu1—N1—C8	−134.7 (3)	C10—N1—C8—C9	−0.7 (4)
O3^ii—Cu1—N1—C8	45.3 (3)	Cu1—N1—C8—C9	171.8 (2)
Cu1—O1—C1—O2	9.4 (4)	N1—C8—C9—N2	0.7 (4)
Cu1—O1—C1—C2	−170.1 (2)	C10—N2—C9—C8	−0.4 (4)
O2—C1—C2—C7	25.4 (4)	C8—N1—C10—N2	0.5 (4)
O1—C1—C2—C7	−155.1 (3)	Cu1—N1—C10—N2	−172.2 (2)
O2—C1—C2—C3	−152.3 (3)	C9—N2—C10—N1	−0.1 (4)
O1—C1—C2—C3	27.2 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O2^iv	0.85 (1)	1.76 (1)	2.596 (3)	170 (4)
N2—H2n···O1^v	0.85 (1)	2.01 (2)	2.841 (3)	166 (4)

Symmetry codes: (iv) x, y, z+1; (v) −x+1, y−1/2, −z+3/2.