Penta­aqua­(1H-benzimidazole-5,6-di­carboxyl­ato-κN3)copper(II) penta­hydrate

Gao, Q.; Gao, W.-H.; Zhang, C.-Y.; Xie, Y.-B.

doi:10.1107/S1600536808017595

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page m928

doi:10.1107/S1600536808017595

Pentaaqua(1H-benzimidazole-5,6-dicarboxylato-κN³)copper(II) pentahydrate

Qian Gao,^a Wei-Hong Gao,^a Chao-Yan Zhang ^a and Ya-Bo Xie ^a ^*

^aCollege of Environmental and Energy Engineering, Beijing University of Technology, Beijing 100022, People's Republic of China
^*Correspondence e-mail: xieyabo@bjut.edu.cn

(Received 19 November 2007; accepted 11 June 2008; online 19 June 2008)

The title compound, [Cu(C₉H₄N₂O₄)(H₂O)₅]·5H₂O, contains one crystallographically independent Cu^II atom and one 1H-benzimidazole-5,6-dicarboxylate (bdc) ligand, along with five coordinated and five uncoordinated water molecules. The Cu^II atom is six-coordinated by one N atom from the bdc ligand and five O atoms from water molecules, giving an octahedral coordination geometry. Hydrogen bonds link the mononuclear complex and uncoordinated water molecules into a three-dimensional network.

Related literature

For related literature, see: Lemos et al. (2004 ); Park et al. (2006 ); Zhang et al. (2007 ).

Experimental

Crystal data

[Cu(C₉H₄N₂O₄)(H₂O)₅]·5H₂O
M_r = 447.84
Triclinic, $[P \overline 1]$
a = 6.8449 (5) Å
b = 11.4381 (8) Å
c = 12.3549 (9) Å
α = 78.1549 (1)°
β = 78.6224 (1)°
γ = 74.8804 (1)°
V = 903.29 (11) Å³
Z = 2
Mo Kα radiation
μ = 1.28 mm⁻¹
T = 296 (2) K
0.24 × 0.24 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.748, T_max = 0.748
4648 measured reflections
3164 independent reflections
2774 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.092
S = 1.05
3164 reflections
295 parameters
20 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10W—H10A⋯O1Wⁱ	0.80 (3)	2.09 (3)	2.855 (3)	160 (4)
O10W—H10B⋯O3ⁱⁱ	0.81 (3)	2.05 (3)	2.802 (3)	155 (4)
O9W—H9B⋯O4ⁱⁱⁱ	0.81 (3)	1.94 (3)	2.739 (3)	174 (4)
O7W—H7B⋯O6W	0.83 (3)	1.95 (3)	2.758 (4)	166 (4)
O7W—H7A⋯O3	0.81 (3)	1.94 (3)	2.735 (3)	165 (4)
O6W—H6C⋯O2	0.79 (3)	2.03 (3)	2.773 (3)	156 (5)
O6W—H6B⋯O1^iv	0.84 (3)	1.96 (3)	2.772 (4)	162 (5)
O5W—H5A⋯O2^v	0.78 (2)	1.84 (3)	2.611 (3)	170 (4)
O5W—H5B⋯O10W	0.80 (2)	2.01 (3)	2.793 (3)	169 (4)
O4W—H4A⋯O10W^vi	0.81 (3)	1.96 (3)	2.760 (3)	168 (5)
O4W—H4B⋯O7Wⁱⁱ	0.79 (3)	1.97 (3)	2.723 (4)	160 (5)
O3W—H3C⋯O9Wⁱ	0.78 (2)	2.05 (3)	2.820 (3)	172 (4)
O3W—H3B⋯O3ⁱⁱ	0.81 (2)	2.00 (3)	2.800 (3)	170 (4)
O2W—H2A⋯O4^vii	0.82 (3)	1.93 (3)	2.709 (3)	160 (4)
O2W—H2B⋯O9W	0.80 (3)	1.94 (3)	2.735 (3)	172 (4)
O1W—H1D⋯O1^v	0.78 (2)	1.85 (3)	2.621 (3)	170 (4)
N1—H1A⋯O7Wⁱⁱⁱ	0.86	1.97	2.805 (3)	163
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) -x+1, -y+1, -z; (iv) x-1, y, z; (v) -x+1, -y+1, -z+1; (vi) -x+1, -y+2, -z+1; (vii) x-1, y+1, z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017595/kj2082sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017595/kj2082Isup2.hkl

checkCIF report

Comment top

Several coordination polymers formed by the ligand 1H-benzoimidazole-5,6-dicarboxylic acid have been reported recently: µ²-2,2'-Bibenzimidazolato-N',N'',N''')tetrakis (triphenylphosphine)-di-copper(I) dichloromethane solvate (Lemos et al., 2004), catena-poly [tetrakis(µ²Benzimidazolato-N,N')-di-Co(II) unknown clathrate hydrate] (Park et al., 2006), and catena-poly [bis (µ⁵Benzotriazole-5-carboxylate) -bis(µ²-hydroxo)-tri-Co(II)] (Zhang et al., 2007) The first complex is a binuclear structure and the latter two are 3D porous metal-organic frameworks. However, up to now, the Cu^II complex of the 1H-benzoimidazole-5,6-dicarboxylic acid ligand (H₂L), has not been reported.

As shown in Figure 1, the title compound has a mononuclear structure, in which there exists only one crystallographically independent Cu (II) atom and only one 1H-benzoimidazole-5,6-dicarboxylate ligand, along with five coordinated and five uncoordinated water. Each Cu (II) is six-coordinated with one N atom from the ligand, and five O atoms from water molecules, giving an octahedral coordination geometry. Hydrogen bonds link the mononuclear complex and uncoordinated water molecules into a three-dimensional network.

Related literature top

For related literature, see: Lemos et al. (2004); Park et al. (2006); Zhang et al. (2007).

Experimental top

The title complex was synthesized by carefully layering a solution of Cu(NO₃)₂.3H₂O (24 mg, 0.1 mmol) in MeOH (10 ml) on top of a solution of H₂L (27 mg, 0.1 mmol) and LiOH (8.4 mg, 0.2 mmol) in H₂O (10 ml) in a test-tube. After about several months at room temperature, green block-shaped single crystals suitable for X-ray investigation appeared at the boundary between MeOH and H₂O with a yield of 25%.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Structure of the title complex, showing displacement ellipsoids at the 30% probability level.

Pentaaqua(1H-benzimidazole-5,6-dicarboxylato-κN³)copper(II) pentahydrate top

Crystal data top

[Cu(C₉H₄N₂O₄)(H₂O)₅]·5H₂O	Z = 2
M_r = 447.84	F(000) = 466
Triclinic, P1	D_x = 1.647 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8449 (5) Å	Cell parameters from 2164 reflections
b = 11.4381 (8) Å	θ = 2.7–27.7°
c = 12.3549 (9) Å	µ = 1.28 mm⁻¹
α = 78.1549 (1)°	T = 296 K
β = 78.6224 (1)°	Block, green
γ = 74.8804 (1)°	0.24 × 0.24 × 0.24 mm
V = 903.29 (11) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3164 independent reflections
Radiation source: fine-focus sealed tube	2774 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −8→7
T_min = 0.748, T_max = 0.748	k = −13→9
4648 measured reflections	l = −14→13

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0394P)² + 1.2855P] where P = (F_o² + 2F_c²)/3
3164 reflections	(Δ/σ)_max = 0.001
295 parameters	Δρ_max = 0.32 e Å⁻³
20 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

[Cu(C₉H₄N₂O₄)(H₂O)₅]·5H₂O	γ = 74.8804 (1)°
M_r = 447.84	V = 903.29 (11) Å³
Triclinic, P1	Z = 2
a = 6.8449 (5) Å	Mo Kα radiation
b = 11.4381 (8) Å	µ = 1.28 mm⁻¹
c = 12.3549 (9) Å	T = 296 K
α = 78.1549 (1)°	0.24 × 0.24 × 0.24 mm
β = 78.6224 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3164 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2774 reflections with I > 2σ(I)
T_min = 0.748, T_max = 0.748	R_int = 0.018
4648 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	20 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.32 e Å⁻³
3164 reflections	Δρ_min = −0.54 e Å⁻³
295 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
Cu2	0.40064 (5)	0.90276 (3)	0.25900 (3)	0.01956 (13)
C1	0.5610 (5)	0.7927 (3)	0.0504 (2)	0.0208 (6)
H1B	0.5372	0.8719	0.0100	0.025*
C2	0.5701 (4)	0.6408 (2)	0.1857 (2)	0.0155 (6)
C3	0.5523 (4)	0.5625 (2)	0.2878 (2)	0.0164 (6)
H3A	0.4908	0.5933	0.3535	0.020*
C4	0.6288 (4)	0.4374 (2)	0.2891 (2)	0.0164 (6)
C5	0.7248 (4)	0.3904 (3)	0.1890 (2)	0.0174 (6)
C6	0.7410 (5)	0.4686 (3)	0.0879 (2)	0.0209 (6)
H6A	0.8036	0.4385	0.0220	0.025*
C7	0.6613 (4)	0.5927 (3)	0.0878 (2)	0.0188 (6)
C8	0.6183 (4)	0.3556 (2)	0.4017 (2)	0.0181 (6)
C9	0.7972 (5)	0.2539 (3)	0.1890 (2)	0.0200 (6)
N1	0.6497 (4)	0.6937 (2)	0.0032 (2)	0.0232 (6)
H1A	0.6921	0.6925	−0.0670	0.028*
N2	0.5095 (4)	0.7684 (2)	0.16013 (19)	0.0178 (5)
O1	0.7832 (3)	0.3070 (2)	0.43846 (19)	0.0333 (6)
O1W	0.1811 (3)	0.8182 (2)	0.36057 (18)	0.0231 (5)
H1D	0.206 (6)	0.780 (3)	0.418 (2)	0.035*
H1C	0.145 (6)	0.774 (3)	0.331 (3)	0.035*
O2	0.4460 (3)	0.3461 (2)	0.45410 (18)	0.0296 (5)
O2W	0.2065 (4)	0.9916 (2)	0.14521 (19)	0.0267 (5)
H2B	0.151 (6)	0.950 (3)	0.122 (3)	0.040*
H2A	0.119 (5)	1.055 (3)	0.154 (3)	0.040*
O3	0.6926 (3)	0.18604 (18)	0.25581 (18)	0.0281 (5)
O3W	0.6198 (3)	0.9979 (2)	0.16683 (18)	0.0236 (5)
H3B	0.652 (6)	1.045 (3)	0.196 (3)	0.035*
H3C	0.719 (5)	0.957 (3)	0.139 (3)	0.035*
O4	0.9510 (3)	0.21717 (19)	0.12100 (18)	0.0296 (5)
O4W	0.2824 (5)	1.0432 (2)	0.3484 (2)	0.0410 (7)
H4B	0.255 (7)	1.113 (3)	0.320 (4)	0.061*
H4A	0.275 (7)	1.030 (4)	0.416 (2)	0.061*
O5W	0.6079 (3)	0.8194 (2)	0.36953 (18)	0.0241 (5)
H5B	0.647 (6)	0.873 (3)	0.385 (3)	0.036*
H5A	0.579 (6)	0.775 (3)	0.424 (2)	0.036*
O6W	0.0815 (4)	0.4415 (2)	0.3683 (2)	0.0397 (6)
H6B	−0.005 (6)	0.402 (4)	0.403 (4)	0.060*
H6C	0.164 (6)	0.421 (4)	0.410 (3)	0.060*
O7W	0.2891 (4)	0.2718 (2)	0.2314 (2)	0.0330 (5)
H7A	0.406 (4)	0.257 (4)	0.244 (4)	0.050*
H7B	0.224 (6)	0.331 (3)	0.262 (3)	0.050*
O8W	0.9900 (4)	0.6813 (2)	0.2776 (2)	0.0353 (6)
H8B	0.874 (4)	0.710 (4)	0.303 (3)	0.053*
H8A	1.008 (7)	0.609 (3)	0.303 (4)	0.053*
O9W	−0.0044 (4)	0.8476 (2)	0.0862 (2)	0.0339 (6)
H9B	0.018 (7)	0.825 (4)	0.027 (3)	0.051*
H9A	0.013 (7)	0.789 (3)	0.133 (3)	0.051*
O10W	0.8011 (4)	0.9835 (2)	0.4212 (2)	0.0312 (5)
H10B	0.779 (6)	1.053 (3)	0.387 (3)	0.047*
H10A	0.919 (4)	0.953 (4)	0.402 (3)	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu2	0.0244 (2)	0.0145 (2)	0.0180 (2)	−0.00297 (14)	−0.00237 (14)	−0.00150 (14)
C1	0.0287 (16)	0.0122 (14)	0.0197 (15)	−0.0042 (12)	−0.0049 (12)	0.0018 (11)
C2	0.0185 (14)	0.0112 (13)	0.0165 (14)	−0.0022 (11)	−0.0039 (11)	−0.0021 (11)
C3	0.0208 (15)	0.0161 (14)	0.0120 (13)	−0.0041 (11)	−0.0004 (11)	−0.0040 (11)
C4	0.0193 (14)	0.0141 (14)	0.0159 (14)	−0.0041 (11)	−0.0056 (11)	0.0005 (11)
C5	0.0193 (14)	0.0140 (14)	0.0183 (14)	−0.0022 (11)	−0.0033 (11)	−0.0031 (11)
C6	0.0280 (16)	0.0184 (15)	0.0141 (14)	−0.0040 (12)	0.0024 (12)	−0.0046 (11)
C7	0.0242 (15)	0.0157 (14)	0.0146 (14)	−0.0038 (12)	−0.0028 (11)	0.0010 (11)
C8	0.0270 (16)	0.0118 (14)	0.0153 (14)	−0.0054 (12)	−0.0039 (12)	0.0000 (11)
C9	0.0253 (16)	0.0148 (14)	0.0203 (15)	−0.0010 (12)	−0.0084 (12)	−0.0037 (12)
N1	0.0372 (15)	0.0161 (13)	0.0117 (12)	−0.0040 (11)	0.0002 (11)	0.0016 (10)
N2	0.0240 (13)	0.0106 (12)	0.0168 (12)	−0.0022 (10)	−0.0031 (10)	−0.0002 (9)
O1	0.0296 (13)	0.0388 (14)	0.0270 (12)	−0.0103 (10)	−0.0113 (10)	0.0145 (10)
O1W	0.0278 (12)	0.0234 (12)	0.0173 (11)	−0.0090 (9)	−0.0051 (9)	0.0038 (9)
O2	0.0263 (12)	0.0315 (13)	0.0239 (12)	−0.0079 (10)	−0.0016 (9)	0.0111 (10)
O2W	0.0290 (13)	0.0182 (12)	0.0315 (12)	0.0036 (9)	−0.0134 (10)	−0.0038 (10)
O3	0.0342 (13)	0.0142 (11)	0.0338 (13)	−0.0069 (9)	−0.0013 (10)	−0.0013 (9)
O3W	0.0270 (12)	0.0193 (11)	0.0253 (12)	−0.0088 (9)	0.0003 (9)	−0.0050 (9)
O4	0.0333 (13)	0.0177 (11)	0.0302 (12)	0.0044 (9)	0.0016 (10)	−0.0061 (9)
O4W	0.0744 (19)	0.0175 (12)	0.0255 (13)	−0.0081 (12)	0.0065 (13)	−0.0079 (11)
O5W	0.0322 (12)	0.0231 (12)	0.0182 (11)	−0.0122 (10)	−0.0075 (9)	0.0053 (9)
O6W	0.0334 (15)	0.0358 (15)	0.0475 (17)	−0.0081 (12)	−0.0107 (12)	0.0035 (12)
O7W	0.0357 (14)	0.0362 (14)	0.0265 (12)	−0.0074 (12)	−0.0041 (11)	−0.0054 (10)
O8W	0.0307 (13)	0.0291 (13)	0.0446 (15)	−0.0055 (11)	−0.0069 (11)	−0.0029 (11)
O9W	0.0407 (14)	0.0334 (14)	0.0280 (13)	−0.0050 (11)	−0.0076 (11)	−0.0080 (11)
O10W	0.0313 (13)	0.0268 (13)	0.0305 (13)	−0.0033 (11)	−0.0033 (11)	0.0007 (10)

Geometric parameters (Å, º) top

Cu2—O4W	2.037 (2)	C9—O4	1.248 (4)
Cu2—O2W	2.055 (2)	C9—O3	1.261 (4)
Cu2—N2	2.055 (2)	N1—H1A	0.8600
Cu2—O1W	2.070 (2)	O1W—H1D	0.78 (2)
Cu2—O5W	2.076 (2)	O1W—H1C	0.80 (2)
Cu2—O3W	2.097 (2)	O2W—H2B	0.80 (3)
C1—N2	1.322 (4)	O2W—H2A	0.82 (3)
C1—N1	1.328 (4)	O3W—H3B	0.81 (2)
C1—H1B	0.9300	O3W—H3C	0.78 (2)
C2—C3	1.393 (4)	O4W—H4B	0.79 (3)
C2—N2	1.396 (3)	O4W—H4A	0.81 (3)
C2—C7	1.397 (4)	O5W—H5B	0.80 (2)
C3—C4	1.387 (4)	O5W—H5A	0.78 (2)
C3—H3A	0.9300	O6W—H6B	0.84 (3)
C4—C5	1.420 (4)	O6W—H6C	0.79 (3)
C4—C8	1.510 (4)	O7W—H7A	0.81 (3)
C5—C6	1.382 (4)	O7W—H7B	0.83 (3)
C5—C9	1.510 (4)	O8W—H8B	0.80 (3)
C6—C7	1.381 (4)	O8W—H8A	0.81 (3)
C6—H6A	0.9300	O9W—H9B	0.81 (3)
C7—N1	1.387 (4)	O9W—H9A	0.79 (3)
C8—O2	1.248 (4)	O10W—H10B	0.81 (3)
C8—O1	1.249 (4)	O10W—H10A	0.80 (3)

O4W—Cu2—O2W	88.82 (10)	C6—C7—C2	122.3 (3)
O4W—Cu2—N2	176.07 (10)	N1—C7—C2	105.0 (2)
O2W—Cu2—N2	87.32 (9)	O2—C8—O1	124.5 (3)
O4W—Cu2—O1W	86.06 (10)	O2—C8—C4	118.2 (2)
O2W—Cu2—O1W	92.49 (9)	O1—C8—C4	117.3 (3)
N2—Cu2—O1W	94.83 (9)	O4—C9—O3	125.0 (3)
O4W—Cu2—O5W	90.71 (11)	O4—C9—C5	117.9 (3)
O2W—Cu2—O5W	176.77 (9)	O3—C9—C5	117.0 (3)
N2—Cu2—O5W	93.11 (9)	C1—N1—C7	107.4 (2)
O1W—Cu2—O5W	90.66 (9)	C1—N1—H1A	126.3
O4W—Cu2—O3W	89.28 (10)	C7—N1—H1A	126.3
O2W—Cu2—O3W	89.14 (9)	C1—N2—C2	104.4 (2)
N2—Cu2—O3W	89.94 (9)	C1—N2—Cu2	122.93 (19)
O1W—Cu2—O3W	175.03 (9)	C2—N2—Cu2	132.25 (19)
O5W—Cu2—O3W	87.67 (9)	Cu2—O1W—H1D	118 (3)
N2—C1—N1	113.8 (2)	Cu2—O1W—H1C	113 (3)
N2—C1—H1B	123.1	H1D—O1W—H1C	106 (4)
N1—C1—H1B	123.1	Cu2—O2W—H2B	117 (3)
C3—C2—N2	130.6 (3)	Cu2—O2W—H2A	123 (3)
C3—C2—C7	120.0 (3)	H2B—O2W—H2A	105 (4)
N2—C2—C7	109.4 (2)	Cu2—O3W—H3B	118 (3)
C4—C3—C2	118.3 (3)	Cu2—O3W—H3C	115 (3)
C4—C3—H3A	120.8	H3B—O3W—H3C	109 (4)
C2—C3—H3A	120.8	Cu2—O4W—H4B	123 (3)
C3—C4—C5	120.9 (3)	Cu2—O4W—H4A	120 (3)
C3—C4—C8	117.1 (2)	H4B—O4W—H4A	116 (5)
C5—C4—C8	121.9 (2)	Cu2—O5W—H5B	107 (3)
C6—C5—C4	120.5 (3)	Cu2—O5W—H5A	122 (3)
C6—C5—C9	118.4 (3)	H5B—O5W—H5A	109 (4)
C4—C5—C9	121.0 (3)	H6B—O6W—H6C	100 (5)
C7—C6—C5	117.9 (3)	H7A—O7W—H7B	107 (4)
C7—C6—H6A	121.0	H8B—O8W—H8A	104 (5)
C5—C6—H6A	121.0	H9B—O9W—H9A	108 (4)
C6—C7—N1	132.7 (3)	H10B—O10W—H10A	107 (4)

N2—C2—C3—C4	−179.4 (3)	C4—C5—C9—O4	−148.5 (3)
C7—C2—C3—C4	0.6 (4)	C6—C5—C9—O3	−141.7 (3)
C2—C3—C4—C5	0.7 (4)	C4—C5—C9—O3	33.8 (4)
C2—C3—C4—C8	176.6 (3)	N2—C1—N1—C7	−0.4 (4)
C3—C4—C5—C6	−1.1 (4)	C6—C7—N1—C1	−178.6 (3)
C8—C4—C5—C6	−176.7 (3)	C2—C7—N1—C1	1.0 (3)
C3—C4—C5—C9	−176.4 (3)	N1—C1—N2—C2	−0.5 (3)
C8—C4—C5—C9	7.9 (4)	N1—C1—N2—Cu2	172.7 (2)
C4—C5—C6—C7	0.1 (4)	C3—C2—N2—C1	−178.9 (3)
C9—C5—C6—C7	175.5 (3)	C7—C2—N2—C1	1.1 (3)
C5—C6—C7—N1	−179.2 (3)	C3—C2—N2—Cu2	8.8 (5)
C5—C6—C7—C2	1.3 (5)	C7—C2—N2—Cu2	−171.1 (2)
C3—C2—C7—C6	−1.6 (5)	O2W—Cu2—N2—C1	47.3 (2)
N2—C2—C7—C6	178.3 (3)	O1W—Cu2—N2—C1	139.6 (2)
C3—C2—C7—N1	178.7 (3)	O5W—Cu2—N2—C1	−129.5 (2)
N2—C2—C7—N1	−1.3 (3)	O3W—Cu2—N2—C1	−41.8 (2)
C3—C4—C8—O2	67.2 (4)	O2W—Cu2—N2—C2	−141.6 (3)
C5—C4—C8—O2	−116.9 (3)	O1W—Cu2—N2—C2	−49.4 (3)
C3—C4—C8—O1	−109.2 (3)	O5W—Cu2—N2—C2	41.6 (3)
C5—C4—C8—O1	66.7 (4)	O3W—Cu2—N2—C2	129.2 (3)
C6—C5—C9—O4	36.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10W—H10A···O1Wⁱ	0.80 (3)	2.09 (3)	2.855 (3)	160 (4)
O10W—H10B···O3ⁱⁱ	0.81 (3)	2.05 (3)	2.802 (3)	155 (4)
O9W—H9B···O4ⁱⁱⁱ	0.81 (3)	1.94 (3)	2.739 (3)	174 (4)
O7W—H7B···O6W	0.83 (3)	1.95 (3)	2.758 (4)	166 (4)
O7W—H7A···O3	0.81 (3)	1.94 (3)	2.735 (3)	165 (4)
O6W—H6C···O2	0.79 (3)	2.03 (3)	2.773 (3)	156 (5)
O6W—H6B···O1^iv	0.84 (3)	1.96 (3)	2.772 (4)	162 (5)
O5W—H5A···O2^v	0.78 (2)	1.84 (3)	2.611 (3)	170 (4)
O5W—H5B···O10W	0.80 (2)	2.01 (3)	2.793 (3)	169 (4)
O4W—H4A···O10W^vi	0.81 (3)	1.96 (3)	2.760 (3)	168 (5)
O4W—H4B···O7Wⁱⁱ	0.79 (3)	1.97 (3)	2.723 (4)	160 (5)
O3W—H3C···O9Wⁱ	0.78 (2)	2.05 (3)	2.820 (3)	172 (4)
O3W—H3B···O3ⁱⁱ	0.81 (2)	2.00 (3)	2.800 (3)	170 (4)
O2W—H2A···O4^vii	0.82 (3)	1.93 (3)	2.709 (3)	160 (4)
O2W—H2B···O9W	0.80 (3)	1.94 (3)	2.735 (3)	172 (4)
O1W—H1D···O1^v	0.78 (2)	1.85 (3)	2.621 (3)	170 (4)
N1—H1A···O7Wⁱⁱⁱ	0.86	1.97	2.805 (3)	163

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

Experimental details

Crystal data
Chemical formula	[Cu(C₉H₄N₂O₄)(H₂O)₅]·5H₂O
M_r	447.84
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.8449 (5), 11.4381 (8), 12.3549 (9)
α, β, γ (°)	78.1549 (1), 78.6224 (1), 74.8804 (1)
V (Å³)	903.29 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.28
Crystal size (mm)	0.24 × 0.24 × 0.24

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.748, 0.748
No. of measured, independent and observed [I > 2σ(I)] reflections	4648, 3164, 2774
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.05
No. of reflections	3164
No. of parameters	295
No. of restraints	20
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.54

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10W—H10A···O1Wⁱ	0.80 (3)	2.09 (3)	2.855 (3)	160 (4)
O10W—H10B···O3ⁱⁱ	0.81 (3)	2.05 (3)	2.802 (3)	155 (4)
O9W—H9B···O4ⁱⁱⁱ	0.81 (3)	1.94 (3)	2.739 (3)	174 (4)
O7W—H7B···O6W	0.83 (3)	1.95 (3)	2.758 (4)	166 (4)
O7W—H7A···O3	0.81 (3)	1.94 (3)	2.735 (3)	165 (4)
O6W—H6C···O2	0.79 (3)	2.03 (3)	2.773 (3)	156 (5)
O6W—H6B···O1^iv	0.84 (3)	1.96 (3)	2.772 (4)	162 (5)
O5W—H5A···O2^v	0.78 (2)	1.84 (3)	2.611 (3)	170 (4)
O5W—H5B···O10W	0.80 (2)	2.01 (3)	2.793 (3)	169 (4)
O4W—H4A···O10W^vi	0.81 (3)	1.96 (3)	2.760 (3)	168 (5)
O4W—H4B···O7Wⁱⁱ	0.79 (3)	1.97 (3)	2.723 (4)	160 (5)
O3W—H3C···O9Wⁱ	0.78 (2)	2.05 (3)	2.820 (3)	172 (4)
O3W—H3B···O3ⁱⁱ	0.81 (2)	2.00 (3)	2.800 (3)	170 (4)
O2W—H2A···O4^vii	0.82 (3)	1.93 (3)	2.709 (3)	160 (4)
O2W—H2B···O9W	0.80 (3)	1.94 (3)	2.735 (3)	172 (4)
O1W—H1D···O1^v	0.78 (2)	1.85 (3)	2.621 (3)	170 (4)
N1—H1A···O7Wⁱⁱⁱ	0.86	1.97	2.805 (3)	162.5

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

Acknowledgements

This work was supported by the Funding Project for Academic Human Resources Development in Institutions of Higher Learning under the Jurisdiction of Beijing Municipality.

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lemos, S. S., Deflon, V. M., Bessler, K. E., Abbott, M. P. & Niquet, E. (2004). Transition Met. Chem. 29, 46–50. Web of Science CSD CrossRef CAS Google Scholar
Park, K. S., Ni, Z., Choi, J. Y., Huang, R., Uribe-Romo, F. J., Chae, H. K., O'Keeffe, M. & Yaghi, O. M. (2006). Proc. Natl Acad. Sci. USA, 103, 10186–10191. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, X.-M., Hao, Z.-M., Zhang, W.-X. & Chen, X.-M. (2007). Angew. Chem. Int. Ed. 46, 3456–3459. Web of Science CSD CrossRef CAS Google Scholar

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Volume 64| Part 7| July 2008| Page m928

doi:10.1107/S1600536808017595

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