A second polymorph of aqua­(2,9-di­methyl-1,10-phenanthroline-κ2N,N′)bis­(formato-κO)copper(II)

Lin, J.-L.; Xu, W.; Xie, H.-Z.

doi:10.1107/S1600536808022812

metal-organic compounds

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Volume 64| Part 8| August 2008| Page m1062

doi:10.1107/S1600536808022812

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A second polymorph of aqua(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)bis(formato-κO)copper(II)

Jian-Li Lin,^a ^* Wei Xu ^a and Hong-Zhen Xie ^a

^aState Key Laboratory Base of Novel Functional Materials and Preparation Science, Faculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, People's Republic of China
^*Correspondence e-mail: zhengyueqing@nbu.edu.cn

(Received 17 June 2008; accepted 21 July 2008; online 26 July 2008)

A new monoclinic polymorphic form of the title compound, [Cu(HCO₂)₂(C₁₄H₁₂N₂)(H₂O)], is described. It differs from the first orthorhombic polymorph [Pan, Lin & Zheng (2005 ). Z. Kristallogr. New Cryst. Struct. 220, 495–496] in the deviation of the Cu atom relative to the plane of the 2,9-dimethyl-1,10-phenanthroline (dmp) ligand. In the present structure, the Cu atom is shifted from the mean plane of the dmp ligand by only 0.005 (1) Å, compared with 0.318 (6) Å in the orthorhombic form. Hydrogen-bonding and π–π stacking interactions (mean interplanar distance of 3.59 Å in the title compound) in the two different polymorphs are both essential to the supramolecular assembly.

Related literature

For the orthorhombic polymorph, see: Pan et al. (2005).

Experimental

Crystal data

[Cu(HCO₂)₂(C₁₄H₁₂N₂)(H₂O)]
M_r = 379.85
Monoclinic, P 2₁ /c
a = 10.669 (2) Å
b = 7.7677 (16) Å
c = 19.338 (4) Å
β = 94.22 (3)°
V = 1598.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.40 mm⁻¹
T = 295 (2) K
0.26 × 0.17 × 0.09 mm

Data collection

Bruker P4 diffractometer
Absorption correction: multi-scan (XSCANS; Siemens, 1996 ) T_min = 0.749, T_max = 0.879
15099 measured reflections
3632 independent reflections
3202 reflections with I > 2σ(I)
R_int = 0.019
3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.072
S = 1.06
3632 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu—O1	1.9450 (12)
Cu—O3	1.9546 (12)
Cu—O5	1.9726 (12)
Cu—N1	2.0328 (13)
Cu—N2	2.2801 (15)

O1—Cu—O3	95.53 (6)
O1—Cu—O5	87.40 (6)
O1—Cu—N1	174.06 (6)
O1—Cu—N2	107.40 (6)
O3—Cu—O5	167.05 (6)
O3—Cu—N1	86.33 (5)
O3—Cu—N2	95.28 (6)
O5—Cu—N1	89.57 (5)
O5—Cu—N2	95.87 (5)
N1—Cu—N2	77.98 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5C⋯O2ⁱ	0.88	1.86	2.714 (2)	166
O5—H5B⋯O4ⁱⁱ	0.89	1.72	2.605 (2)	175
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z.

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022812/fj2128sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022812/fj2128Isup2.hkl

checkCIF report

Comment top

We reported a structure of the copper-dmp complex aqua-(2,9-dimethyl-1,10-phenanthroline-κ²N:N')-diromato-copper(II) previously, which crystallizes in space group Pna2₁ (Pan, et al.,2005). On repeating the experiment recently, to our surprise, we found a new polyporph, (I), that had crystallized in the space group P2₁/c.

The crystal structure of the title compound is very similar to the previously reported complex, built up by the [Cu(dmp)(H₂O)(HCOO)₂] complex molecules. The Cu atoms are each square pyramidally coordinated by two N atoms of one dmp ligand, three O atoms of two formate anions and one water molecule with the N2 atom of the dmp ligand at the apical position. The apical and basal Cu—N bond distances are 2.280 (1) and 2.033 (2) Å, respectively. The Cu—O bond distances to the formate anions are 1.945 (1) and 1.955 (1) Å, slightly longer than that to the water molecule (1.973 (1) Å). Suggesting that the formate anions possess better coordinating capability to the water molecule in the structure, which also show no significant difference from the isomer crystal structure that reported by us. The Cu atom is shifted by 0.153 (1) Å from the equatorial plane through N1, O1, O3 and O5 atoms towards the apical N2 atom. Through the intermolecular hydrogen bond the complex molecules are link into double chains with the chelating dmp ligands extending parallelly on one side along [010]. The substituted phenanthroline ligands of one double chain protrude into the grooves between adjacent aromatic planes of the neighboring double chain, yielding two-dimensional layers parallel to (100). It is found that the assembly of the double chains is due to interchain π-π stacking interactions between the dmp ligands (mean interplanar distance: 3.59 Å).

Related literature top

For the first orthorhom polymorph, see: Pan et al. (2005).

Experimental top

Dropwise addition of 2.0 ml (1.0 M) Na₂CO₃ to an aqueous solution of 0.075 g (0.442 mmol) CuCl₂.2H₂O in 5.0 ml H₂O yielded pale blue deposit, which was separated by centrifugation and washed with doubly distilled water until no Cl^- anions are detectable in the supernatant. The precipitate was then added to a solution of 0.100 g (0.442 mmol) 2,9-dimethyl-1,10-phenanthroline in a mixed solvent consisting of 15 ml H₂O and 15 ml me thanol. To the mixture 1.77 ml (1.0 M) formic acid was dropped and the precipitate was slowly dissolved under continuous stirring. The resulting blue solution was allowed to stand at room temperature, and slow evaporation for 10 days afforded blue plate crystals.

Computing details top

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

Figures top

	Fig. 1. ORTEP view of the title compound. The displacement ellipsoids are drawn at 40% probability level.
	Fig. 2. A perspective view of the crystal structure of (I), with hydrogen bonds shown as dashed lines.

aqua(2,9-dimethyl-1,10-phenanthroline- κ²N,N')bis(formato-κO)copper(II) top

Crystal data top

[Cu(HCO₂)₂(C₁₄H₁₂N₂)(H₂O)]	F(000) = 780
M_r = 379.85	D_x = 1.579 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.669 (2) Å	θ = 5.0–12.5°
b = 7.7677 (16) Å	µ = 1.40 mm⁻¹
c = 19.338 (4) Å	T = 295 K
β = 94.22 (3)°	Plate, blue
V = 1598.3 (6) Å³	0.26 × 0.17 × 0.09 mm
Z = 4

Data collection top

Bruker P4 diffractometer	3202 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.019
Graphite monochromator	θ_max = 27.5°, θ_min = 3.3°
θ/2θ scans	h = −13→13
Absorption correction: multi-scan (XSCANS; Siemens, 1996)	k = −10→9
T_min = 0.749, T_max = 0.879	l = −24→25
15099 measured reflections	3 standard reflections every 97 reflections
3632 independent reflections	intensity decay: none

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0413P)² + 0.5201P] where P = (F_o² + 2F_c²)/3
3632 reflections	(Δ/σ)_max = 0.001
219 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

[Cu(HCO₂)₂(C₁₄H₁₂N₂)(H₂O)]	V = 1598.3 (6) Å³
M_r = 379.85	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.669 (2) Å	µ = 1.40 mm⁻¹
b = 7.7677 (16) Å	T = 295 K
c = 19.338 (4) Å	0.26 × 0.17 × 0.09 mm
β = 94.22 (3)°

Data collection top

Bruker P4 diffractometer	3202 reflections with I > 2σ(I)
Absorption correction: multi-scan (XSCANS; Siemens, 1996)	R_int = 0.019
T_min = 0.749, T_max = 0.879	3 standard reflections every 97 reflections
15099 measured reflections	intensity decay: none
3632 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.072	H-atom parameters constrained
S = 1.06	Δρ_max = 0.35 e Å⁻³
3632 reflections	Δρ_min = −0.22 e Å⁻³
219 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
Cu	0.209657 (18)	0.90493 (2)	0.156116 (9)	0.02440 (7)
N1	0.21922 (12)	0.80402 (17)	0.05966 (6)	0.0257 (3)
N2	0.42113 (13)	0.89494 (17)	0.14606 (7)	0.0275 (3)
C1	0.11886 (17)	0.7632 (2)	0.01841 (9)	0.0325 (4)
C2	0.1317 (2)	0.6999 (3)	−0.04910 (10)	0.0472 (5)
H2A	0.0605	0.6741	−0.0778	0.057*
C3	0.2471 (2)	0.6765 (3)	−0.07224 (10)	0.0508 (5)
H3A	0.2552	0.6332	−0.1165	0.061*
C4	0.35505 (19)	0.7178 (3)	−0.02912 (9)	0.0393 (4)
C5	0.4803 (2)	0.6986 (3)	−0.04949 (11)	0.0541 (6)
H5A	0.4929	0.6540	−0.0931	0.065*
C6	0.5804 (2)	0.7435 (3)	−0.00711 (11)	0.0537 (6)
H6A	0.6609	0.7298	−0.0217	0.064*
C7	0.56433 (17)	0.8120 (3)	0.05998 (10)	0.0397 (4)
C8	0.66470 (19)	0.8661 (3)	0.10598 (12)	0.0511 (5)
H8A	0.7468	0.8577	0.0931	0.061*
C9	0.64241 (19)	0.9302 (3)	0.16884 (12)	0.0478 (5)
H9A	0.7091	0.9659	0.1992	0.057*
C10	0.51845 (17)	0.9430 (2)	0.18838 (9)	0.0350 (4)
C11	0.44274 (15)	0.8321 (2)	0.08260 (8)	0.0289 (3)
C12	0.33615 (16)	0.7831 (2)	0.03694 (8)	0.0281 (3)
C13	−0.00801 (18)	0.7856 (3)	0.04536 (10)	0.0438 (4)
H13A	−0.0302	0.6831	0.0694	0.066*
H13B	−0.0691	0.8066	0.0073	0.066*
H13C	−0.0062	0.8816	0.0767	0.066*
C14	0.4920 (2)	1.0068 (3)	0.25888 (10)	0.0537 (6)
H14A	0.4243	1.0884	0.2547	0.081*
H14B	0.5659	1.0614	0.2802	0.081*
H14C	0.4691	0.9116	0.2870	0.081*
O1	0.18364 (13)	0.98991 (18)	0.24857 (6)	0.0408 (3)
O2	−0.02000 (15)	1.0452 (3)	0.22488 (8)	0.0613 (4)
C15	0.0760 (2)	1.0407 (3)	0.26275 (10)	0.0471 (5)
O3	0.18495 (13)	1.12747 (15)	0.10994 (6)	0.0365 (3)
O4	0.18327 (18)	1.41073 (16)	0.10823 (8)	0.0530 (4)
C16	0.19793 (18)	1.2723 (2)	0.13792 (9)	0.0360 (4)
O5	0.19568 (12)	0.67025 (15)	0.19376 (6)	0.0344 (3)
H5B	0.1958	0.5834	0.1636	0.051*
H5C	0.1416	0.6452	0.2242	0.054*
H15	0.0751	1.0904	0.3111	0.052*
H16	0.2383	1.2705	0.1852	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.02683 (11)	0.02277 (11)	0.02410 (11)	0.00161 (7)	0.00524 (7)	−0.00126 (7)
N1	0.0280 (7)	0.0227 (6)	0.0263 (6)	−0.0003 (5)	0.0021 (5)	−0.0001 (5)
N2	0.0267 (7)	0.0283 (7)	0.0276 (6)	−0.0012 (5)	0.0032 (5)	0.0011 (5)
C1	0.0353 (9)	0.0304 (8)	0.0313 (8)	−0.0023 (7)	−0.0011 (7)	−0.0003 (7)
C2	0.0495 (12)	0.0554 (12)	0.0350 (9)	−0.0055 (10)	−0.0086 (8)	−0.0096 (9)
C3	0.0627 (14)	0.0601 (13)	0.0297 (9)	−0.0010 (11)	0.0040 (9)	−0.0158 (9)
C4	0.0467 (11)	0.0421 (10)	0.0300 (8)	0.0022 (8)	0.0093 (7)	−0.0060 (8)
C5	0.0587 (14)	0.0690 (15)	0.0373 (10)	0.0073 (11)	0.0227 (9)	−0.0110 (10)
C6	0.0430 (12)	0.0737 (15)	0.0474 (11)	0.0080 (10)	0.0234 (9)	−0.0016 (11)
C7	0.0319 (9)	0.0479 (11)	0.0408 (9)	0.0023 (8)	0.0126 (7)	0.0052 (9)
C8	0.0246 (9)	0.0722 (14)	0.0575 (12)	−0.0005 (9)	0.0102 (8)	0.0079 (11)
C9	0.0306 (10)	0.0592 (13)	0.0526 (12)	−0.0096 (9)	−0.0033 (8)	0.0047 (10)
C10	0.0323 (9)	0.0346 (9)	0.0374 (9)	−0.0041 (7)	−0.0018 (7)	0.0021 (7)
C11	0.0292 (8)	0.0288 (8)	0.0295 (7)	0.0007 (6)	0.0077 (6)	0.0020 (7)
C12	0.0327 (8)	0.0264 (7)	0.0258 (7)	0.0020 (6)	0.0070 (6)	0.0006 (6)
C13	0.0308 (9)	0.0564 (12)	0.0434 (10)	−0.0056 (9)	−0.0033 (8)	0.0005 (9)
C14	0.0484 (12)	0.0687 (15)	0.0426 (11)	−0.0057 (11)	−0.0066 (9)	−0.0160 (11)
O1	0.0475 (8)	0.0463 (8)	0.0293 (6)	0.0104 (6)	0.0073 (5)	−0.0055 (6)
O2	0.0465 (9)	0.0904 (13)	0.0485 (8)	0.0135 (9)	0.0128 (7)	−0.0072 (9)
C15	0.0577 (13)	0.0534 (12)	0.0319 (9)	0.0127 (10)	0.0159 (9)	−0.0061 (9)
O3	0.0529 (8)	0.0249 (6)	0.0319 (6)	0.0037 (5)	0.0045 (5)	0.0000 (5)
O4	0.0859 (12)	0.0259 (7)	0.0479 (8)	0.0012 (7)	0.0098 (8)	0.0004 (6)
C16	0.0443 (10)	0.0292 (9)	0.0346 (8)	−0.0012 (7)	0.0028 (7)	−0.0013 (7)
O5	0.0415 (7)	0.0271 (6)	0.0359 (6)	−0.0028 (5)	0.0122 (5)	0.0032 (5)

Geometric parameters (Å, º) top

Cu—O1	1.9450 (12)	C7—C11	1.408 (2)
Cu—O3	1.9546 (12)	C8—C9	1.351 (3)
Cu—O5	1.9726 (12)	C8—H8A	0.9300
Cu—N1	2.0328 (13)	C9—C10	1.405 (3)
Cu—N2	2.2801 (15)	C9—H9A	0.9300
N1—C1	1.326 (2)	C10—C14	1.497 (3)
N1—C12	1.363 (2)	C11—C12	1.439 (2)
N2—C10	1.327 (2)	C13—H13A	0.9600
N2—C11	1.356 (2)	C13—H13B	0.9600
C1—C2	1.411 (2)	C13—H13C	0.9600
C1—C13	1.496 (3)	C14—H14A	0.9600
C2—C3	1.353 (3)	C14—H14B	0.9600
C2—H2A	0.9300	C14—H14C	0.9600
C3—C4	1.408 (3)	O1—C15	1.264 (2)
C3—H3A	0.9300	O2—C15	1.215 (3)
C4—C12	1.403 (2)	C15—H15	1.0122
C4—C5	1.429 (3)	O3—C16	1.252 (2)
C5—C6	1.343 (3)	O4—C16	1.223 (2)
C5—H5A	0.9300	C16—H16	0.9821
C6—C7	1.424 (3)	O5—H5B	0.8914
C6—H6A	0.9300	O5—H5C	0.8760
C7—C8	1.405 (3)

O1—Cu—O3	95.53 (6)	C9—C8—H8A	119.9
O1—Cu—O5	87.40 (6)	C7—C8—H8A	119.9
O1—Cu—N1	174.06 (6)	C8—C9—C10	119.97 (19)
O1—Cu—N2	107.40 (6)	C8—C9—H9A	120.0
O3—Cu—O5	167.05 (6)	C10—C9—H9A	120.0
O3—Cu—N1	86.33 (5)	N2—C10—C9	121.54 (18)
O3—Cu—N2	95.28 (6)	N2—C10—C14	117.62 (17)
O5—Cu—N1	89.57 (5)	C9—C10—C14	120.81 (18)
O5—Cu—N2	95.87 (5)	N2—C11—C7	122.89 (16)
N1—Cu—N2	77.98 (6)	N2—C11—C12	118.11 (14)
C1—N1—C12	119.71 (14)	C7—C11—C12	119.01 (15)
C1—N1—Cu	123.47 (11)	N1—C12—C4	122.22 (16)
C12—N1—Cu	116.80 (11)	N1—C12—C11	118.15 (14)
C10—N2—C11	118.80 (15)	C4—C12—C11	119.63 (16)
C10—N2—Cu	132.20 (12)	C1—C13—H13A	109.5
C11—N2—Cu	108.95 (11)	C1—C13—H13B	109.5
N1—C1—C2	120.71 (17)	H13A—C13—H13B	109.5
N1—C1—C13	118.29 (15)	C1—C13—H13C	109.5
C2—C1—C13	121.00 (17)	H13A—C13—H13C	109.5
C3—C2—C1	120.38 (18)	H13B—C13—H13C	109.5
C3—C2—H2A	119.8	C10—C14—H14A	109.5
C1—C2—H2A	119.8	C10—C14—H14B	109.5
C2—C3—C4	119.86 (17)	H14A—C14—H14B	109.5
C2—C3—H3A	120.1	C10—C14—H14C	109.5
C4—C3—H3A	120.1	H14A—C14—H14C	109.5
C12—C4—C3	117.10 (18)	H14B—C14—H14C	109.5
C12—C4—C5	119.28 (18)	C15—O1—Cu	119.93 (13)
C3—C4—C5	123.61 (18)	O2—C15—O1	128.13 (18)
C6—C5—C4	121.48 (18)	O2—C15—H15	118.8
C6—C5—H5A	119.3	O1—C15—H15	112.9
C4—C5—H5A	119.3	C16—O3—Cu	126.20 (12)
C5—C6—C7	120.61 (18)	O4—C16—O3	125.51 (17)
C5—C6—H6A	119.7	O4—C16—H16	118.8
C7—C6—H6A	119.7	O3—C16—H16	114.6
C8—C7—C11	116.55 (17)	Cu—O5—H5B	117.0
C8—C7—C6	123.44 (18)	Cu—O5—H5C	121.6
C11—C7—C6	119.99 (19)	H5B—O5—H5C	107.7
C9—C8—C7	120.23 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5C···O2ⁱ	0.88	1.86	2.714 (2)	166
O5—H5B···O4ⁱⁱ	0.89	1.72	2.605 (2)	175

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

Experimental details

Crystal data
Chemical formula	[Cu(HCO₂)₂(C₁₄H₁₂N₂)(H₂O)]
M_r	379.85
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.669 (2), 7.7677 (16), 19.338 (4)
β (°)	94.22 (3)
V (Å³)	1598.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.40
Crystal size (mm)	0.26 × 0.17 × 0.09

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	Multi-scan (XSCANS; Siemens, 1996)
T_min, T_max	0.749, 0.879
No. of measured, independent and observed [I > 2σ(I)] reflections	15099, 3632, 3202
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.072, 1.06
No. of reflections	3632
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.22

Computer programs: XSCANS (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu—O1	1.9450 (12)	Cu—N1	2.0328 (13)
Cu—O3	1.9546 (12)	Cu—N2	2.2801 (15)
Cu—O5	1.9726 (12)

O1—Cu—O3	95.53 (6)	O3—Cu—N1	86.33 (5)
O1—Cu—O5	87.40 (6)	O3—Cu—N2	95.28 (6)
O1—Cu—N1	174.06 (6)	O5—Cu—N1	89.57 (5)
O1—Cu—N2	107.40 (6)	O5—Cu—N2	95.87 (5)
O3—Cu—O5	167.05 (6)	N1—Cu—N2	77.98 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5C···O2ⁱ	0.88	1.86	2.714 (2)	166
O5—H5B···O4ⁱⁱ	0.89	1.72	2.605 (2)	175

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

Acknowledgements

This project was sponsored by the K. C. Wong Magna Fund in Ningbo University, the Expert Project of Key Basic Research of the Ministry of Science and Technology of China (grant No. 2003CCA00800), and the Ningbo Municipal Natural Science Foundation (grant No. 2006 A610061).

References

Pan, J. G., Lin, J. L. & Zheng, Y. Q. (2005). Z. Kristallogr. New Cryst. Struct. 220, 495–496. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

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