Aqua­(2,2′-biimidazole)(pyridine-2,6-dicarboxyl­ato)copper(II) monohydrate

Cao, M.-N.; Wang, M.; Luo, F.; Cheng, C.; Hu, Z.

doi:10.1107/S1600536807040366

Aqua(2,2′-biimidazole)(pyridine-2,6-dicarboxylato)copper(II) monohydrate

M.-N. Cao, M. Wang, F. Luo, C. Cheng and Z. Hu

In the title compound, [Cu(C₇H₃NO₄)(C₆H₆N₄)(H₂O)]·H₂O, the central Cu^II ion exhibits a distorted mer-CuN₃O₃ octahedral geometry arising from one water O atom, an N,N-bidentate 2,2′-biimidazole molecule and an N,O,O-tridentate pyridine-2,6-dicarboxylate dianion. The crystal packing is stabilized by O—H

O, N—H

O and C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040366/hb2508sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040366/hb2508Isup2.hkl Contains datablock I

CCDC reference: 660130

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.006 Å
R factor = 0.049
wR factor = 0.148
Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O6     -   H6B    ...          ?

Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C5     -   C7     ...       1.53 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.82(7), Rep     0.83(3) ......       2.33 su-Ra
              O6   -H6B     1.555   1.555

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.31
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          8

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   1 ALERT type 5 Informative message, check

Comment top

Biimidazole (H₂biim) is a bidentate chelating ligand with multiple proton-donor sites which can coordinate to a transition metal in its neutral (H₂biim), singly-deprotonated (Hbiim^-) and doubly-deprotonated (biim^2-) forms. Coordinated H₂biim usually forms hydrogen bonds with counteranions or solvent molecules (Whitesides et al., (1991); Rebek,1990).

Here, we report the synthesis and sructure of the the title compound, (I), which contains Cu(II) ions, neutral H₂biim and pyridine-2,6-dicarboxylate (pda) dianions. The Cu^II ion in (I) exhibits a distorted mer-CuN₃O₃ octahedral geometry (Table 1), arising from N1, N2, N4 and O5 as equatorial atoms and O1 and O3 as axial atoms.

The packing for (I) is mainly governed by a combination of O(or N, C)–H···O hydrogen bonds (Table 2, Fig. 2) linking the constituent species together.

Related literature top

For related literature, see: Whitesides et al. (1991); Rebek (1990); Xiao & Shreeve (2005).

Experimental top

2,2'-biimidazole was synthesized according to the literature procedure (Xiao & Shreeve, 2005). A mixture of Cu(NO₃)₂·4H₂O, pyridine-2,6-dicarboxylic acid, 2,2'-biimidazole and water in a molar ratio of 1:1:1:555 was sealed in a 23 ml polyfluoroethylene-lined stainless steel bomb and heated to 423 K under autogenous pressure for 72 h. After slowly cooling to room temperature and opening the bomb, blue plates of (I) were formed, collected by filtration, washed in deionized water, and finally dried.

Structure description top

The packing for (I) is mainly governed by a combination of O(or N, C)–H···O hydrogen bonds (Table 2, Fig. 2) linking the constituent species together.

For related literature, see: Whitesides et al. (1991); Rebek (1990); Xiao & Shreeve (2005).

Computing details top

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

Figures top

	Fig. 1. View of the molecular structure of (I), showing 50% probability displacement ellipsoids for the non-hydrogen atoms.
	Fig. 2. Part of the crystal structure of (I) showing the formation of the two-dimensinal network. Hydrogen bonds are shown as dashed lines.

Aqua(2,2'-biimidazole)(pyridine-2,6-dicarboxylato)copper(II) monohydrate top

Crystal data top

[Cu(C₇H₃NO₄)(C₆H₆N₄)(H₂O)]·H₂O	Z = 2
M_r = 398.82	F(000) = 406
Triclinic, P1	D_x = 1.711 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5951 (4) Å	Cell parameters from 3382 reflections
b = 10.6971 (7) Å	θ = 2.5–27.8°
c = 11.6112 (7) Å	µ = 1.46 mm⁻¹
α = 97.210 (1)°	T = 296 K
β = 94.384 (1)°	Plate, blue
γ = 106.411 (1)°	0.35 × 0.10 × 0.06 mm
V = 774.16 (8) Å³

Data collection top

Bruker SMART CCD diffractometer	2978 independent reflections
Radiation source: fine-focus sealed tube	2595 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
T_min = 0.630, T_max = 0.918	k = −13→13
7976 measured reflections	l = −14→12

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0837P)² + 1.1035P] where P = (F_o² + 2F_c²)/3
2978 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.82 e Å⁻³
8 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Cu(C₇H₃NO₄)(C₆H₆N₄)(H₂O)]·H₂O	γ = 106.411 (1)°
M_r = 398.82	V = 774.16 (8) Å³
Triclinic, P1	Z = 2
a = 6.5951 (4) Å	Mo Kα radiation
b = 10.6971 (7) Å	µ = 1.46 mm⁻¹
c = 11.6112 (7) Å	T = 296 K
α = 97.210 (1)°	0.35 × 0.10 × 0.06 mm
β = 94.384 (1)°

Data collection top

Bruker SMART CCD diffractometer	2978 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2595 reflections with I > 2σ(I)
T_min = 0.630, T_max = 0.918	R_int = 0.029
7976 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	8 restraints
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.82 e Å⁻³
2978 reflections	Δρ_min = −0.52 e Å⁻³
244 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	0.72700 (7)	0.86989 (4)	0.73050 (4)	0.0290 (2)
C1	0.6942 (6)	0.5957 (3)	0.7217 (3)	0.0269 (8)
C2	0.5990 (7)	0.4613 (4)	0.6989 (4)	0.0376 (10)
H2	0.6697	0.4032	0.7225	0.045*
C3	0.3954 (7)	0.4149 (4)	0.6399 (4)	0.0411 (10)
H3	0.3290	0.3245	0.6229	0.049*
C4	0.2892 (6)	0.5014 (4)	0.6059 (4)	0.0345 (9)
H4	0.1518	0.4711	0.5670	0.041*
C5	0.3952 (6)	0.6344 (3)	0.6320 (3)	0.0261 (8)
C6	0.9129 (6)	0.6668 (4)	0.7889 (3)	0.0277 (8)
C7	0.3065 (6)	0.7458 (4)	0.6035 (3)	0.0281 (8)
C8	0.5874 (6)	0.7965 (4)	0.9848 (4)	0.0348 (9)
H8	0.5183	0.7064	0.9679	0.042*
C9	0.6372 (6)	0.8679 (4)	1.0932 (4)	0.0341 (9)
H9	0.6103	0.8369	1.1635	0.041*
C10	0.7441 (5)	0.9956 (3)	0.9642 (3)	0.0252 (8)
C11	0.8339 (5)	1.1019 (3)	0.9001 (3)	0.0266 (8)
C12	0.9225 (6)	1.1865 (4)	0.7462 (4)	0.0348 (9)
H12	0.9476	1.1949	0.6694	0.042*
C13	0.9615 (7)	1.2875 (4)	0.8357 (4)	0.0379 (10)
H13	1.0156	1.3769	0.8315	0.046*
N1	0.5914 (5)	0.6780 (3)	0.6882 (3)	0.0240 (6)
N2	0.6540 (5)	0.8769 (3)	0.9036 (3)	0.0286 (7)
N4	0.8402 (5)	1.0698 (3)	0.7868 (3)	0.0292 (7)
N3	0.7358 (5)	0.9956 (3)	1.0784 (3)	0.0301 (7)
H3A	0.789 (7)	1.059 (3)	1.131 (3)	0.036*
N5	0.9061 (5)	1.2329 (3)	0.9335 (3)	0.0296 (7)
H5C	0.908 (7)	1.274 (4)	1.000 (3)	0.036*
O1	0.9727 (4)	0.7904 (2)	0.7902 (2)	0.0286 (6)
O2	1.0086 (5)	0.6037 (3)	0.8420 (3)	0.0425 (8)
O3	0.4277 (4)	0.8609 (3)	0.6434 (3)	0.0380 (7)
O4	0.1318 (5)	0.7184 (3)	0.5452 (3)	0.0406 (7)
O5	0.8806 (5)	0.8899 (3)	0.5814 (3)	0.0366 (7)
H5A	0.957 (7)	0.844 (5)	0.569 (4)	0.055*
H5B	0.808 (7)	0.895 (5)	0.520 (3)	0.055*
O6	0.3788 (10)	0.0955 (4)	0.6068 (4)	0.0869 (16)
H6A	0.378 (13)	0.025 (4)	0.632 (7)	0.130*
H6B	0.480 (10)	0.158 (5)	0.639 (7)	0.130*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0276 (3)	0.0193 (3)	0.0376 (3)	0.00591 (19)	−0.0040 (2)	0.0020 (2)
C1	0.031 (2)	0.0192 (16)	0.0275 (19)	0.0061 (14)	−0.0043 (15)	0.0013 (14)
C2	0.038 (2)	0.0214 (18)	0.053 (3)	0.0122 (17)	−0.0073 (19)	0.0037 (18)
C3	0.039 (2)	0.0196 (18)	0.057 (3)	0.0010 (17)	−0.007 (2)	0.0006 (18)
C4	0.029 (2)	0.0236 (18)	0.042 (2)	0.0003 (15)	−0.0056 (17)	−0.0038 (17)
C5	0.0279 (19)	0.0209 (17)	0.0274 (19)	0.0065 (14)	−0.0038 (15)	0.0015 (14)
C6	0.0250 (18)	0.0266 (18)	0.031 (2)	0.0103 (15)	−0.0012 (15)	−0.0026 (15)
C7	0.0277 (19)	0.0259 (18)	0.033 (2)	0.0121 (15)	0.0000 (16)	0.0039 (15)
C8	0.029 (2)	0.0257 (19)	0.049 (3)	0.0062 (16)	0.0053 (18)	0.0071 (18)
C9	0.027 (2)	0.037 (2)	0.041 (2)	0.0114 (17)	0.0029 (17)	0.0113 (18)
C10	0.0174 (16)	0.0228 (17)	0.036 (2)	0.0088 (13)	−0.0022 (14)	0.0036 (15)
C11	0.0197 (17)	0.0188 (16)	0.039 (2)	0.0060 (13)	−0.0024 (15)	−0.0001 (15)
C12	0.033 (2)	0.0236 (18)	0.046 (2)	0.0059 (16)	−0.0005 (18)	0.0088 (17)
C13	0.035 (2)	0.0228 (19)	0.052 (3)	0.0047 (16)	−0.0067 (19)	0.0087 (18)
N1	0.0237 (15)	0.0190 (14)	0.0272 (16)	0.0061 (12)	−0.0032 (12)	0.0000 (12)
N2	0.0235 (15)	0.0214 (15)	0.0389 (19)	0.0056 (12)	0.0017 (13)	0.0009 (13)
N4	0.0273 (16)	0.0180 (14)	0.041 (2)	0.0069 (12)	−0.0018 (14)	0.0026 (13)
N3	0.0222 (16)	0.0287 (16)	0.037 (2)	0.0071 (13)	−0.0029 (13)	−0.0002 (14)
N5	0.0276 (16)	0.0180 (15)	0.041 (2)	0.0076 (12)	−0.0036 (14)	−0.0019 (13)
O1	0.0271 (13)	0.0215 (12)	0.0340 (15)	0.0065 (10)	−0.0060 (11)	−0.0003 (11)
O2	0.0399 (17)	0.0316 (15)	0.055 (2)	0.0174 (13)	−0.0175 (14)	0.0022 (14)
O3	0.0305 (15)	0.0226 (13)	0.0584 (19)	0.0087 (11)	−0.0122 (13)	0.0053 (13)
O4	0.0340 (16)	0.0369 (16)	0.0474 (18)	0.0156 (13)	−0.0170 (13)	−0.0050 (14)
O5	0.0457 (18)	0.0357 (16)	0.0323 (16)	0.0185 (13)	0.0007 (13)	0.0065 (13)
O6	0.147 (5)	0.045 (2)	0.069 (3)	0.048 (3)	−0.043 (3)	−0.004 (2)

Geometric parameters (Å, º) top

Cu1—N1	1.974 (3)	C8—C9	1.353 (6)
Cu1—N4	2.056 (3)	C8—N2	1.369 (5)
Cu1—O5	2.076 (3)	C8—H8	0.9300
Cu1—N2	2.100 (3)	C9—N3	1.376 (5)
Cu1—O3	2.120 (3)	C9—H9	0.9300
Cu1—O1	2.141 (3)	C10—N2	1.321 (5)
C1—N1	1.330 (5)	C10—N3	1.331 (5)
C1—C2	1.378 (5)	C10—C11	1.449 (5)
C1—C6	1.525 (5)	C11—N4	1.324 (5)
C2—C3	1.384 (6)	C11—N5	1.341 (5)
C2—H2	0.9300	C12—C13	1.354 (6)
C3—C4	1.385 (6)	C12—N4	1.371 (5)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.379 (5)	C13—N5	1.369 (6)
C4—H4	0.9300	C13—H13	0.9300
C5—N1	1.331 (5)	N3—H3A	0.83 (3)
C5—C7	1.529 (5)	N5—H5C	0.83 (3)
C6—O2	1.233 (5)	O5—H5A	0.80 (3)
C6—O1	1.267 (4)	O5—H5B	0.84 (3)
C7—O4	1.229 (5)	O6—H6A	0.84 (3)
C7—O3	1.270 (5)	O6—H6B	0.83 (3)

N1—Cu1—N4	173.29 (12)	N2—C8—H8	125.2
N1—Cu1—O5	95.10 (12)	C8—C9—N3	106.1 (4)
N4—Cu1—O5	91.07 (13)	C8—C9—H9	127.0
N1—Cu1—N2	94.58 (12)	N3—C9—H9	127.0
N4—Cu1—N2	79.94 (12)	N2—C10—N3	111.8 (3)
O5—Cu1—N2	164.58 (13)	N2—C10—C11	117.7 (3)
N1—Cu1—O3	77.85 (11)	N3—C10—C11	130.6 (3)
N4—Cu1—O3	99.15 (11)	N4—C11—N5	111.4 (3)
O5—Cu1—O3	93.90 (13)	N4—C11—C10	117.1 (3)
N2—Cu1—O3	99.86 (13)	N5—C11—C10	131.4 (4)
N1—Cu1—O1	77.50 (11)	C13—C12—N4	109.2 (4)
N4—Cu1—O1	105.69 (11)	C13—C12—H12	125.4
O5—Cu1—O1	85.31 (11)	N4—C12—H12	125.4
N2—Cu1—O1	85.10 (11)	C12—C13—N5	106.8 (3)
O3—Cu1—O1	155.16 (10)	C12—C13—H13	126.6
N1—C1—C2	120.4 (4)	N5—C13—H13	126.6
N1—C1—C6	112.9 (3)	C1—N1—C5	121.7 (3)
C2—C1—C6	126.6 (4)	C1—N1—Cu1	119.1 (2)
C1—C2—C3	118.3 (4)	C5—N1—Cu1	119.0 (2)
C1—C2—H2	120.8	C10—N2—C8	105.5 (3)
C3—C2—H2	120.8	C10—N2—Cu1	110.9 (2)
C2—C3—C4	120.8 (4)	C8—N2—Cu1	141.3 (3)
C2—C3—H3	119.6	C11—N4—C12	105.8 (3)
C4—C3—H3	119.6	C11—N4—Cu1	113.0 (2)
C5—C4—C3	117.4 (4)	C12—N4—Cu1	141.3 (3)
C5—C4—H4	121.3	C10—N3—C9	107.0 (3)
C3—C4—H4	121.3	C10—N3—H3A	127 (3)
N1—C5—C4	121.3 (3)	C9—N3—H3A	126 (3)
N1—C5—C7	112.9 (3)	C11—N5—C13	106.8 (3)
C4—C5—C7	125.7 (3)	C11—N5—H5C	127 (3)
O2—C6—O1	125.9 (4)	C13—N5—H5C	126 (3)
O2—C6—C1	119.3 (3)	C6—O1—Cu1	114.4 (2)
O1—C6—C1	114.7 (3)	C7—O3—Cu1	115.6 (2)
O4—C7—O3	126.3 (3)	Cu1—O5—H5A	116 (4)
O4—C7—C5	119.2 (3)	Cu1—O5—H5B	117 (4)
O3—C7—C5	114.4 (3)	H5A—O5—H5B	113 (4)
C9—C8—N2	109.7 (3)	H6A—O6—H6B	112 (5)
C9—C8—H8	125.2

N1—C1—C2—C3	0.3 (6)	N4—Cu1—N2—C10	−10.2 (2)
C6—C1—C2—C3	177.6 (4)	O5—Cu1—N2—C10	44.9 (6)
C1—C2—C3—C4	−0.7 (7)	O3—Cu1—N2—C10	−107.9 (2)
C2—C3—C4—C5	0.7 (7)	O1—Cu1—N2—C10	96.7 (3)
C3—C4—C5—N1	−0.3 (6)	N1—Cu1—N2—C8	14.6 (4)
C3—C4—C5—C7	−179.4 (4)	N4—Cu1—N2—C8	−169.3 (4)
N1—C1—C6—O2	167.6 (3)	O5—Cu1—N2—C8	−114.1 (5)
C2—C1—C6—O2	−9.9 (6)	O3—Cu1—N2—C8	93.1 (4)
N1—C1—C6—O1	−8.0 (5)	O1—Cu1—N2—C8	−62.4 (4)
C2—C1—C6—O1	174.5 (4)	N5—C11—N4—C12	0.5 (4)
N1—C5—C7—O4	175.4 (4)	C10—C11—N4—C12	177.6 (3)
C4—C5—C7—O4	−5.4 (6)	N5—C11—N4—Cu1	−179.2 (2)
N1—C5—C7—O3	−3.9 (5)	C10—C11—N4—Cu1	−2.1 (4)
C4—C5—C7—O3	175.3 (4)	C13—C12—N4—C11	−0.9 (4)
N2—C8—C9—N3	0.4 (5)	C13—C12—N4—Cu1	178.6 (3)
N2—C10—C11—N4	−7.3 (5)	O5—Cu1—N4—C11	−160.8 (3)
N3—C10—C11—N4	172.6 (4)	N2—Cu1—N4—C11	6.6 (3)
N2—C10—C11—N5	169.0 (4)	O3—Cu1—N4—C11	105.0 (3)
N3—C10—C11—N5	−11.1 (7)	O1—Cu1—N4—C11	−75.4 (3)
N4—C12—C13—N5	1.0 (5)	O5—Cu1—N4—C12	19.6 (4)
C2—C1—N1—C5	0.0 (6)	N2—Cu1—N4—C12	−173.0 (4)
C6—C1—N1—C5	−177.6 (3)	O3—Cu1—N4—C12	−74.5 (4)
C2—C1—N1—Cu1	176.5 (3)	O1—Cu1—N4—C12	105.1 (4)
C6—C1—N1—Cu1	−1.1 (4)	N2—C10—N3—C9	1.2 (4)
C4—C5—N1—C1	−0.1 (6)	C11—C10—N3—C9	−178.7 (4)
C7—C5—N1—C1	179.1 (3)	C8—C9—N3—C10	−0.9 (4)
C4—C5—N1—Cu1	−176.5 (3)	N4—C11—N5—C13	0.1 (4)
C7—C5—N1—Cu1	2.6 (4)	C10—C11—N5—C13	−176.4 (4)
O5—Cu1—N1—C1	89.7 (3)	C12—C13—N5—C11	−0.6 (4)
N2—Cu1—N1—C1	−78.3 (3)	O2—C6—O1—Cu1	−162.8 (3)
O3—Cu1—N1—C1	−177.4 (3)	C1—C6—O1—Cu1	12.5 (4)
O1—Cu1—N1—C1	5.7 (3)	N1—Cu1—O1—C6	−10.3 (3)
O5—Cu1—N1—C5	−93.7 (3)	N4—Cu1—O1—C6	163.6 (3)
N2—Cu1—N1—C5	98.3 (3)	O5—Cu1—O1—C6	−106.6 (3)
O3—Cu1—N1—C5	−0.8 (3)	N2—Cu1—O1—C6	85.5 (3)
O1—Cu1—N1—C5	−177.8 (3)	O3—Cu1—O1—C6	−17.4 (4)
N3—C10—N2—C8	−0.9 (4)	O4—C7—O3—Cu1	−176.0 (3)
C11—C10—N2—C8	179.0 (3)	C5—C7—O3—Cu1	3.2 (4)
N3—C10—N2—Cu1	−167.5 (2)	N1—Cu1—O3—C7	−1.5 (3)
C11—C10—N2—Cu1	12.4 (4)	N4—Cu1—O3—C7	−175.4 (3)
C9—C8—N2—C10	0.3 (4)	O5—Cu1—O3—C7	92.9 (3)
C9—C8—N2—Cu1	160.1 (3)	N2—Cu1—O3—C7	−94.1 (3)
N1—Cu1—N2—C10	173.7 (3)	O1—Cu1—O3—C7	5.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O3ⁱ	0.84 (3)	1.90 (4)	2.700 (5)	160 (9)
O5—H5B···O6ⁱⁱ	0.84 (3)	1.88 (3)	2.719 (5)	174 (5)
O5—H5A···O4ⁱⁱⁱ	0.80 (3)	2.01 (3)	2.813 (4)	175 (5)
N5—H5C···O2^iv	0.83 (3)	2.05 (3)	2.871 (5)	166 (4)
N3—H3A···O1^iv	0.83 (3)	1.97 (3)	2.729 (4)	152 (4)
C3—H3···O6	0.93	2.55	3.359 (6)	146
C13—H13···O2^v	0.93	2.43	3.298 (5)	156
C4—H4···O4^vi	0.93	2.48	3.294 (5)	147

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

Experimental details

Crystal data
Chemical formula	[Cu(C₇H₃NO₄)(C₆H₆N₄)(H₂O)]·H₂O
M_r	398.82
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.5951 (4), 10.6971 (7), 11.6112 (7)
α, β, γ (°)	97.210 (1), 94.384 (1), 106.411 (1)
V (Å³)	774.16 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.46
Crystal size (mm)	0.35 × 0.10 × 0.06

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.630, 0.918
No. of measured, independent and observed [I > 2σ(I)] reflections	7976, 2978, 2595
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.148, 1.10
No. of reflections	2978
No. of parameters	244
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.52

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).

Selected bond lengths (Å) top

Cu1—N1	1.974 (3)	Cu1—N2	2.100 (3)
Cu1—N4	2.056 (3)	Cu1—O3	2.120 (3)
Cu1—O5	2.076 (3)	Cu1—O1	2.141 (3)