Diaqua­(5-methyl-1H-pyrazole-3-carboxyl­ato)(4-nitro­benzoato)copper(II)

Hu, F.; Yin, X.; Feng, Y.; Mi, Y.; Zhang, S.

doi:10.1107/S160053680900169X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m210

doi:10.1107/S160053680900169X

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Diaqua(5-methyl-1H-pyrazole-3-carboxylato)(4-nitrobenzoato)copper(II)

Fei-long Hu,^a Xian-hong Yin,^a ^* Yu Feng,^a Yan Mi ^a and Shan-shan Zhang ^a

^aCollege of Chemistry and Ecological Engineering, Guangxi University for Nationalities, Nanning 530006, People's Republic of China
^*Correspondence e-mail: yxhphd@163.com

(Received 23 December 2008; accepted 14 January 2009; online 23 January 2009)

In the title complex, [Cu(C₇H₄NO₄)(C₅H₅N₂O₂)(H₂O)₂], the Cu^II ion is coordinated in a slightly distorted square-pyramidal enviroment. The basal plane is formed by an N atom and an O atom from a 5-methyl-1H-pyrazole-3-carboxylate ligand and by two O atoms from two water ligands. The apical position is occupied by a carboxylate O atom from a 4-nitrobenzoate ligand. In the crystal structure, intermolecular O—H⋯O and N—H⋯O hydrogen bonds link complex moleclues, forming extended chains parallel to the a axis.

Related literature

For background information, see: Montoya et al. (2007 ).

Experimental

Crystal data

[Cu(C₇H₄NO₄)(C₅H₅N₂O₂)(H₂O)₂]
M_r = 390.79
Triclinic, $[P \overline 1]$
a = 6.965 (1) Å
b = 9.1860 (13) Å
c = 12.4220 (16) Å
α = 96.633 (1)°
β = 105.116 (2)°
γ = 103.978 (2)°
V = 730.91 (17) Å³
Z = 2
Mo Kα radiation
μ = 1.55 mm⁻¹
T = 298 (2) K
0.40 × 0.21 × 0.20 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.577, T_max = 0.748
3783 measured reflections
2526 independent reflections
2249 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.073
S = 1.04
2526 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O8	1.9344 (17)
Cu1—O7	1.9489 (17)
Cu1—N1	1.970 (2)
Cu1—O1	1.9811 (16)
Cu1—O3	2.3164 (19)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O2ⁱ	0.85	1.96	2.799 (2)	173
O7—H7B⋯O3ⁱⁱ	0.84	1.83	2.631 (2)	157
O8—H8A⋯O1ⁱⁱⁱ	0.85	1.97	2.803 (3)	165
O8—H8B⋯O4ⁱⁱ	0.85	1.78	2.582 (2)	156
N2—H2⋯O2ⁱ	0.86	1.97	2.781 (3)	157
Symmetry codes: (i) x-1, y, z; (ii) -x, -y, -z+2; (iii) -x+1, -y, -z+2.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900169X/lh2751sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900169X/lh2751Isup2.hkl

checkCIF report

Comment top

The chemical and pharmacological properties of pyrazoles have been investigated extensively, owing to their chelating ability with metal ions and their potentially beneficial chemical and biological activities (Montoya et al., 2007.) As part of our studies on the synthesis and characterization of these types of compounds, we report here the synthesis and crystal structure of the title compound (I).

The molecular structure of (I) is shown in Fig. 1. The Cu atom is five-coordinated by four O atoms and one N atom. The basal plane is formed by an N atom and an O atom from a 5-methyl-1H-pyrazole-3-carboxylato ligand and two O atoms from coordinated water molecules. In the crystal structure, intermolecular O—H···O and N—H···O hydrogen bonds (Fig. 2) link complex molecules, to form extended chains parallel to the a axis. The coordinated water molecules act as hydrogen donors for symmetry related carboxyl O atoms (see Table 2). In addition, the crystal structure contains various π-π stacking interactions involving the C7-C12, N1/N2/C2-C4 and Cu1/O1/C1/C2/N1 rings with a range of centroid-to-centroid distances of 3.265 (1)-3.849 (1)Å (see Fig. 3).

Related literature top

For background information, see: Montoya et al. (2007).

Experimental top

5-methyl-1H-pyrazole-3-carboxylic acid,4-nitrobenzoic acid and CuCl₂.6H₂O were available commercially and were used without further purification. Equimolar amounts of 5-methyl-1H-pyrazole-3-carboxylic acid (0.5 mmol, 63.02 mg) and 4-nitrobenzoic acid (0.5 mmol, 83.51 mg) were dissolved in anhydrous alcohol (15 ml). The mixture was stirred to give a clear solution, to this solution was added CuCl₂.6H₂O (0.5 mmol, 113 mg) in anhydrous alcohol (10 ml). After keeping the resulting solution in air to evaporate about half of the solvents, blue prisms of the title compound were formed. The crystals were isolated, washed with alcohol three times and dried in a vacuum desiccator using silica gel (Yield 75%). Elemental analysis: found: C, 36.82; H, 3.38; N, 10.65%. calc. for C₁₂H₁₃CuN₃O₈: C, 36.88; H, 3.35; N, 10.75%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound (I) showing 50% proability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Part of the crystal structure of (I) showing the donor-to-acceptor distances of hydrogen bonds as dashed lines.
	Fig. 3. Part of the crystal structure of (I) illustrating π-π stacking interactions as dashed lines.

Diaqua(5-methyl-1H-pyrazole-3-carboxylato)(4-nitrobenzoato)copper(II) top

Crystal data top

[Cu(C₇H₄NO₄)(C₅H₅N₂O₂)(H₂O)₂]	Z = 2
M_r = 390.79	F(000) = 398
Triclinic, P1	D_x = 1.776 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.965 (1) Å	Cell parameters from 2564 reflections
b = 9.1860 (13) Å	θ = 2.6–27.9°
c = 12.4220 (16) Å	µ = 1.55 mm⁻¹
α = 96.633 (1)°	T = 298 K
β = 105.116 (2)°	Block, blue
γ = 103.978 (2)°	0.40 × 0.21 × 0.20 mm
V = 730.91 (17) Å³

Data collection top

Siemens SMART CCD diffractometer	2526 independent reflections
Radiation source: fine-focus sealed tube	2249 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.577, T_max = 0.748	k = −10→10
3783 measured reflections	l = −10→14

Refinement top

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0335P)² + 0.6897P] where P = (F_o² + 2F_c²)/3
2526 reflections	(Δ/σ)_max = 0.001
218 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Cu(C₇H₄NO₄)(C₅H₅N₂O₂)(H₂O)₂]	γ = 103.978 (2)°
M_r = 390.79	V = 730.91 (17) Å³
Triclinic, P1	Z = 2
a = 6.965 (1) Å	Mo Kα radiation
b = 9.1860 (13) Å	µ = 1.55 mm⁻¹
c = 12.4220 (16) Å	T = 298 K
α = 96.633 (1)°	0.40 × 0.21 × 0.20 mm
β = 105.116 (2)°

Data collection top

Siemens SMART CCD diffractometer	2526 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2249 reflections with I > 2σ(I)
T_min = 0.577, T_max = 0.748	R_int = 0.013
3783 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.04	Δρ_max = 0.39 e Å⁻³
2526 reflections	Δρ_min = −0.32 e Å⁻³
218 parameters

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

	x	y	z	U_iso*/U_eq
Cu1	0.29638 (4)	0.19451 (3)	0.99760 (3)	0.02357 (11)
O1	0.5665 (3)	0.2069 (2)	0.96944 (15)	0.0277 (4)
O2	0.7980 (3)	0.3422 (2)	0.89863 (17)	0.0381 (5)
O3	0.1131 (3)	−0.0129 (2)	0.85168 (15)	0.0304 (4)
O4	−0.1882 (3)	−0.0059 (3)	0.73675 (17)	0.0436 (5)
O5	0.3529 (4)	0.3559 (3)	0.4025 (2)	0.0652 (7)
O6	0.6072 (4)	0.2702 (4)	0.4743 (3)	0.0742 (9)
O7	0.0648 (3)	0.2226 (2)	1.04985 (15)	0.0300 (4)
H7A	−0.0183	0.2515	0.9997	0.045*
H7B	0.0013	0.1397	1.0639	0.045*
O8	0.3635 (3)	0.0686 (2)	1.10838 (15)	0.0307 (4)
H8A	0.3628	−0.0188	1.0768	0.046*
H8B	0.2798	0.0576	1.1478	0.046*
N1	0.2972 (3)	0.3507 (2)	0.90140 (17)	0.0220 (4)
N2	0.1750 (3)	0.4334 (2)	0.85329 (17)	0.0240 (4)
H2	0.0547	0.4290	0.8609	0.029*
N3	0.4354 (4)	0.2843 (3)	0.4672 (2)	0.0445 (6)
C1	0.6256 (4)	0.3104 (3)	0.9141 (2)	0.0240 (5)
C2	0.4692 (3)	0.3913 (3)	0.8697 (2)	0.0212 (5)
C3	0.4564 (4)	0.5001 (3)	0.8016 (2)	0.0265 (5)
H3	0.5558	0.5468	0.7693	0.032*
C4	0.2652 (4)	0.5246 (3)	0.7917 (2)	0.0265 (5)
C5	0.1576 (5)	0.6251 (4)	0.7292 (3)	0.0449 (8)
H5A	0.0132	0.5718	0.6957	0.067*
H5B	0.2181	0.6526	0.6707	0.067*
H5C	0.1721	0.7159	0.7811	0.067*
C6	0.0028 (4)	0.0150 (3)	0.7621 (2)	0.0272 (6)
C7	0.1138 (4)	0.0802 (3)	0.6810 (2)	0.0252 (5)
C8	0.3027 (4)	0.0557 (3)	0.6794 (2)	0.0293 (6)
H8	0.3590	−0.0045	0.7267	0.035*
C9	0.4072 (4)	0.1196 (3)	0.6083 (2)	0.0321 (6)
H9	0.5324	0.1022	0.6064	0.038*
C10	0.3217 (4)	0.2099 (3)	0.5403 (2)	0.0311 (6)
C11	0.1344 (4)	0.2360 (3)	0.5388 (2)	0.0344 (6)
H11	0.0796	0.2969	0.4916	0.041*
C12	0.0298 (4)	0.1692 (3)	0.6095 (2)	0.0318 (6)
H12	−0.0978	0.1841	0.6090	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01987 (17)	0.02766 (19)	0.02970 (19)	0.00910 (12)	0.01187 (13)	0.01551 (13)
O1	0.0231 (9)	0.0327 (10)	0.0370 (10)	0.0137 (8)	0.0148 (8)	0.0191 (8)
O2	0.0228 (10)	0.0500 (13)	0.0556 (13)	0.0161 (9)	0.0218 (9)	0.0290 (10)
O3	0.0326 (10)	0.0323 (10)	0.0270 (10)	0.0051 (8)	0.0103 (8)	0.0141 (8)
O4	0.0300 (11)	0.0721 (15)	0.0385 (11)	0.0153 (10)	0.0180 (9)	0.0289 (11)
O5	0.0705 (17)	0.0853 (19)	0.0645 (16)	0.0304 (15)	0.0368 (14)	0.0546 (15)
O6	0.0562 (16)	0.110 (2)	0.095 (2)	0.0382 (16)	0.0546 (15)	0.0648 (18)
O7	0.0239 (9)	0.0356 (11)	0.0418 (11)	0.0134 (8)	0.0176 (8)	0.0230 (9)
O8	0.0342 (10)	0.0357 (10)	0.0351 (10)	0.0173 (8)	0.0194 (8)	0.0204 (8)
N1	0.0207 (10)	0.0243 (11)	0.0259 (11)	0.0088 (8)	0.0108 (8)	0.0102 (9)
N2	0.0195 (10)	0.0278 (11)	0.0317 (11)	0.0115 (9)	0.0122 (9)	0.0128 (9)
N3	0.0464 (16)	0.0533 (17)	0.0445 (15)	0.0145 (13)	0.0242 (12)	0.0257 (13)
C1	0.0205 (12)	0.0245 (13)	0.0291 (13)	0.0067 (10)	0.0094 (10)	0.0086 (10)
C2	0.0180 (12)	0.0211 (12)	0.0262 (13)	0.0036 (9)	0.0102 (10)	0.0067 (10)
C3	0.0255 (13)	0.0275 (14)	0.0326 (14)	0.0071 (11)	0.0164 (11)	0.0127 (11)
C4	0.0294 (14)	0.0265 (14)	0.0295 (14)	0.0102 (11)	0.0134 (11)	0.0132 (11)
C5	0.0460 (18)	0.053 (2)	0.0553 (19)	0.0281 (15)	0.0255 (15)	0.0348 (16)
C6	0.0290 (14)	0.0264 (14)	0.0271 (14)	0.0052 (11)	0.0116 (11)	0.0070 (11)
C7	0.0250 (13)	0.0268 (14)	0.0221 (13)	0.0038 (10)	0.0072 (10)	0.0054 (10)
C8	0.0283 (14)	0.0326 (15)	0.0299 (14)	0.0112 (11)	0.0084 (11)	0.0121 (11)
C9	0.0248 (13)	0.0395 (16)	0.0357 (15)	0.0108 (12)	0.0121 (11)	0.0109 (12)
C10	0.0299 (14)	0.0369 (15)	0.0290 (14)	0.0058 (12)	0.0143 (11)	0.0110 (11)
C11	0.0371 (15)	0.0409 (17)	0.0318 (15)	0.0165 (13)	0.0112 (12)	0.0190 (12)
C12	0.0250 (13)	0.0440 (17)	0.0312 (14)	0.0136 (12)	0.0099 (11)	0.0142 (12)

Geometric parameters (Å, º) top

Cu1—O8	1.9344 (17)	C1—C2	1.488 (3)
Cu1—O7	1.9489 (17)	C2—C3	1.387 (3)
Cu1—N1	1.970 (2)	C3—C4	1.380 (3)
Cu1—O1	1.9811 (16)	C3—H3	0.9300
Cu1—O3	2.3164 (19)	C4—C5	1.488 (4)
O1—C1	1.286 (3)	C5—H5A	0.9600
O2—C1	1.236 (3)	C5—H5B	0.9600
O3—C6	1.269 (3)	C5—H5C	0.9600
O4—C6	1.244 (3)	C6—C7	1.515 (3)
O5—N3	1.213 (3)	C7—C12	1.388 (4)
O6—N3	1.216 (3)	C7—C8	1.392 (4)
O7—H7A	0.8468	C8—C9	1.379 (4)
O7—H7B	0.8446	C8—H8	0.9300
O8—H8A	0.8503	C9—C10	1.376 (4)
O8—H8B	0.8496	C9—H9	0.9300
N1—C2	1.339 (3)	C10—C11	1.378 (4)
N1—N2	1.345 (3)	C11—C12	1.386 (4)
N2—C4	1.352 (3)	C11—H11	0.9300
N2—H2	0.8599	C12—H12	0.9300
N3—C10	1.475 (3)

O8—Cu1—O7	91.42 (7)	C4—C3—C2	105.6 (2)
O8—Cu1—N1	166.43 (8)	C4—C3—H3	127.2
O7—Cu1—N1	96.45 (7)	C2—C3—H3	127.2
O8—Cu1—O1	88.78 (7)	N2—C4—C3	106.6 (2)
O7—Cu1—O1	167.50 (8)	N2—C4—C5	121.2 (2)
N1—Cu1—O1	81.15 (7)	C3—C4—C5	132.2 (2)
O8—Cu1—O3	93.71 (7)	C4—C5—H5A	109.5
O7—Cu1—O3	97.90 (7)	C4—C5—H5B	109.5
N1—Cu1—O3	96.12 (7)	H5A—C5—H5B	109.5
O1—Cu1—O3	94.56 (7)	C4—C5—H5C	109.5
C1—O1—Cu1	115.62 (15)	H5A—C5—H5C	109.5
C6—O3—Cu1	116.46 (16)	H5B—C5—H5C	109.5
Cu1—O7—H7A	110.3	O4—C6—O3	125.0 (2)
Cu1—O7—H7B	109.9	O4—C6—C7	118.0 (2)
H7A—O7—H7B	109.5	O3—C6—C7	117.0 (2)
Cu1—O8—H8A	111.4	C12—C7—C8	119.3 (2)
Cu1—O8—H8B	111.3	C12—C7—C6	119.8 (2)
H8A—O8—H8B	109.4	C8—C7—C6	120.8 (2)
C2—N1—N2	105.59 (19)	C9—C8—C7	120.7 (2)
C2—N1—Cu1	114.33 (15)	C9—C8—H8	119.6
N2—N1—Cu1	140.08 (16)	C7—C8—H8	119.6
N1—N2—C4	111.61 (19)	C10—C9—C8	118.4 (2)
N1—N2—H2	124.2	C10—C9—H9	120.8
C4—N2—H2	124.2	C8—C9—H9	120.8
O5—N3—O6	123.2 (3)	C9—C10—C11	122.6 (2)
O5—N3—C10	118.5 (2)	C9—C10—N3	119.2 (2)
O6—N3—C10	118.3 (2)	C11—C10—N3	118.2 (2)
O2—C1—O1	123.6 (2)	C10—C11—C12	118.3 (2)
O2—C1—C2	121.8 (2)	C10—C11—H11	120.9
O1—C1—C2	114.6 (2)	C12—C11—H11	120.9
N1—C2—C3	110.7 (2)	C11—C12—C7	120.6 (2)
N1—C2—C1	114.0 (2)	C11—C12—H12	119.7
C3—C2—C1	135.4 (2)	C7—C12—H12	119.7

O8—Cu1—O1—C1	−165.77 (18)	O1—C1—C2—C3	−175.1 (3)
O7—Cu1—O1—C1	−74.7 (4)	N1—C2—C3—C4	−0.4 (3)
N1—Cu1—O1—C1	5.10 (18)	C1—C2—C3—C4	179.1 (3)
O3—Cu1—O1—C1	100.61 (18)	N1—N2—C4—C3	−0.5 (3)
O8—Cu1—O3—C6	167.18 (17)	N1—N2—C4—C5	179.1 (2)
O7—Cu1—O3—C6	75.23 (18)	C2—C3—C4—N2	0.6 (3)
N1—Cu1—O3—C6	−22.18 (18)	C2—C3—C4—C5	−179.1 (3)
O1—Cu1—O3—C6	−103.75 (17)	Cu1—O3—C6—O4	−100.5 (3)
O8—Cu1—N1—C2	40.1 (4)	Cu1—O3—C6—C7	78.9 (2)
O7—Cu1—N1—C2	165.23 (17)	O4—C6—C7—C12	25.6 (4)
O1—Cu1—N1—C2	−2.40 (17)	O3—C6—C7—C12	−153.8 (2)
O3—Cu1—N1—C2	−96.07 (17)	O4—C6—C7—C8	−156.2 (3)
O8—Cu1—N1—N2	−140.9 (3)	O3—C6—C7—C8	24.3 (4)
O7—Cu1—N1—N2	−15.8 (3)	C12—C7—C8—C9	0.5 (4)
O1—Cu1—N1—N2	176.6 (3)	C6—C7—C8—C9	−177.7 (2)
O3—Cu1—N1—N2	82.9 (3)	C7—C8—C9—C10	0.9 (4)
C2—N1—N2—C4	0.3 (3)	C8—C9—C10—C11	−1.4 (4)
Cu1—N1—N2—C4	−178.7 (2)	C8—C9—C10—N3	177.5 (3)
Cu1—O1—C1—O2	173.2 (2)	O5—N3—C10—C9	175.5 (3)
Cu1—O1—C1—C2	−6.5 (3)	O6—N3—C10—C9	−4.0 (4)
N2—N1—C2—C3	0.1 (3)	O5—N3—C10—C11	−5.5 (4)
Cu1—N1—C2—C3	179.42 (17)	O6—N3—C10—C11	174.9 (3)
N2—N1—C2—C1	−179.5 (2)	C9—C10—C11—C12	0.4 (4)
Cu1—N1—C2—C1	−0.2 (3)	N3—C10—C11—C12	−178.4 (3)
O2—C1—C2—N1	−175.2 (2)	C10—C11—C12—C7	1.0 (4)
O1—C1—C2—N1	4.5 (3)	C8—C7—C12—C11	−1.4 (4)
O2—C1—C2—C3	5.2 (5)	C6—C7—C12—C11	176.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O2ⁱ	0.85	1.96	2.799 (2)	173
O7—H7B···O3ⁱⁱ	0.84	1.83	2.631 (2)	157
O8—H8A···O1ⁱⁱⁱ	0.85	1.97	2.803 (3)	165
O8—H8B···O4ⁱⁱ	0.85	1.78	2.582 (2)	156
N2—H2···O2ⁱ	0.86	1.97	2.781 (3)	157

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

Experimental details

Crystal data
Chemical formula	[Cu(C₇H₄NO₄)(C₅H₅N₂O₂)(H₂O)₂]
M_r	390.79
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.965 (1), 9.1860 (13), 12.4220 (16)
α, β, γ (°)	96.633 (1), 105.116 (2), 103.978 (2)
V (Å³)	730.91 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.55
Crystal size (mm)	0.40 × 0.21 × 0.20

Data collection
Diffractometer	Siemens SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.577, 0.748
No. of measured, independent and observed [I > 2σ(I)] reflections	3783, 2526, 2249
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.073, 1.04
No. of reflections	2526
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.32

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O8	1.9344 (17)	Cu1—O1	1.9811 (16)
Cu1—O7	1.9489 (17)	Cu1—O3	2.3164 (19)
Cu1—N1	1.970 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O2ⁱ	0.85	1.96	2.799 (2)	172.6
O7—H7B···O3ⁱⁱ	0.84	1.83	2.631 (2)	156.8
O8—H8A···O1ⁱⁱⁱ	0.85	1.97	2.803 (3)	165.3
O8—H8B···O4ⁱⁱ	0.85	1.78	2.582 (2)	155.9
N2—H2···O2ⁱ	0.86	1.97	2.781 (3)	156.5

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

Acknowledgements

The authors thank the National Natural Science Foundation of China (20761002), the Natural Science Foundation of Guangxi (0832080), the Ministry of Education, Science and Technology Key Projects (205121) and the Science Foundation of the State Ethnic Affairs Commission (07GX05). The project was supported by the Open Fund of the Key Laboratory of Development & Application of Forest Chemicals of Guangxi (GXFC08–07), the Fund of the Talent Highland Research Program of Guangxi University, the Development Foundation of Guangxi Research Institute of the Chemical Industry, the Science Foundation of Guangxi University for Nationalities (0409032, 0409012,0509ZD047) and the Innovation Project of Guangxi University for Nationalities (gxun-chx0876).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Montoya, V., Pons, J., Garcia-Antón, J., Solans, X., Font-Bardia, M. & Ros, J. (2007). Inorg. Chim. Acta, 360, 625–637. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

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Volume 65| Part 2| February 2009| Page m210

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