catena-Poly[[[bis­(nitrato-κO)copper(II)]-bis­[μ-1,3-bis­(imidazol-1-yl)-5-methyl­benzene-κ2N3:N3′]] dihydrate]

Liu, G.-X.

doi:10.1107/S1600536812023628

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m840

doi:10.1107/S1600536812023628

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catena-Poly[[[bis(nitrato-κO)copper(II)]-bis[μ-1,3-bis(imidazol-1-yl)-5-methylbenzene-κ²N³:N^3′]] dihydrate]

Guang-Xiang Liu ^a ^*

^aSchool of Biochemical and Environmental Engineering, Nanjing Xiaozhuang University, Nanjing 211171, People's Republic of China
^*Correspondence e-mail: liugx@njxzc.edu.cn

(Received 5 May 2012; accepted 24 May 2012; online 31 May 2012)

In the title complex, {[Cu(NO₃)₂(C₁₃H₁₂N₄)₂]·2H₂O}_n, the Cu^II atom is located on a crystallographic center of symmetry and adopts an N₄O₂ octahedral coordination geometry with four imidazole N atoms in the equatorial sites and two O atoms in the axial sites. The dihedral angles between the central benzene ring and the imidazole rings are 4.93 (11) and 46.08 (12)°. The 1,3-bis(imidazol-1-yl)-5-methylbenzene ligand is bis-monodentate, linking symmetry-related Cu^II atoms into sheets in the bc plane. These sheets are further bridged into a three-dimensional supramolecular structure by O—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For background to the coordination chemistry of imidazole derivates, see: Huang et al. (2006 ); Wang et al. (2008 ); Tian et al. (2007 ); Jin et al. (2008 ). For imidazole ligands bearing rigid spacers, see: Qi et al. (2008 ); Li et al. (2007 ); Zhang et al. (2008 ). For the synthesis, see: Altman & Buchwald (2006 ).

Experimental

Crystal data

[Cu(NO₃)₂(C₁₃H₁₂N₄)₂]·2H₂O
M_r = 672.12
Monoclinic, P 2₁ /c
a = 11.585 (4) Å
b = 9.652 (3) Å
c = 15.450 (4) Å
β = 123.604 (17)°
V = 1438.9 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.83 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.839, T_max = 0.865
10260 measured reflections
2672 independent reflections
2114 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.101
S = 1.06
2672 reflections
214 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O3	0.88 (2)	2.04 (2)	2.909 (6)	170 (4)
O1W—H1WB⋯O3ⁱ	0.86 (2)	2.20 (3)	3.020 (5)	159 (5)
O1W—H1WB⋯O2ⁱ	0.86 (2)	2.42 (4)	3.142 (4)	142 (5)
C2—H2⋯O1Wⁱⁱ	0.93	2.36	3.230 (5)	156
C3—H3⋯O1ⁱⁱⁱ	0.93	2.27	3.186 (4)	167
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x, -y+2, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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 I, global. DOI: 10.1107/S1600536812023628/lr2064sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023628/lr2064Isup2.hkl

checkCIF report

Comment top

Imidazole has been well used in crystal engineering, and some zeolite-like porous frameworks with divalent and tetrahedral metal ions with this ligand have been reported (Huang et al., 2006; Wang et al., 2008; Tian et al., 2007). Meanwhile, a large number of imidazole-containing flexible ligands have been extensively studied, and many fascinating coordination polymers based on such poly(imidazole) ligands have been synthesized (Jin et al., 2008). However, to the best of our knowledge, the research on imidazole ligands bearing rigid spacers is still less developed (Qi et al., 2008; Li et al., 2007; Zhang et al., 2008).

Single-crystal X-ray diffraction analysis reveals that the title compound (I) crystallizes in the monoclinic space group P2₁/c. The geometry of the Cu^II ion is surrounded by four imidazole rings of distinct L ligands and two nitrate anions, which illustrates a slightly distorted octahedral coordination environment (Fig. 1). Notably, as shown in Fig. 2, the four-coordinated Cu^II center is connected by the bent ligand L into a two-dimensional sheets in the bc plane. Within the ligand, the dihedral angle between the central benzene ring and terminal imidazole ring is 4.93 (11) and 46.08 (12), respectively. These sheets are further bridged into a three-dimensional supramolecular structure by O—H···O and C—H···O hydrogen bonds (Fig. 3).

Related literature top

For background to the coordination chemistry of imidazole derivates, see: Huang et al. (2006); Wang et al. (2008); Tian et al. (2007); Jin et al. (2008). For imidazole ligands bearing rigid spacers, see: Qi et al. (2008); Li et al. (2007); Zhang et al. (2008). For the synthesis, see: Altman et al. (2006).

Experimental top

The ligand was obtained according to the reported procedure (Altman et al., 2006). A mixture of CH₃OH and H₂O (1:1, 8 ml), as a buffer layer, was carefully layered over a solution of Cu(NO₃)₂ (0.02 mmol) in H₂O (6 ml). Then a solution of 5-methyl-1,3-bis(imidazol-1-yl)benzene (L, 0.06 mmol) in CH₃OH (6 ml) was layered over the buffer layer, and the resultant reaction was left to stand at room temperature. After two weeks, blue blocks of (I) appeared at the boundary. Yield: ~40% (based on L).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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. The title complex with displacement ellipsoids shown at the 30% probability level. Hydrogen atoms are omitted for clarity.
	Fig. 2. Lateral view of the two-dimensional sheet in the bc plane of the title complex. Hydrogen atoms, water molecules and nitrate anions are omitted for clarity.
	Fig. 3. The packing diagram of the title complex, showing the hydrogen bonding as dashed lines.

catena-Poly[[[bis(nitrato-κO)copper(II)]-bis[µ-1,3- bis(imidazol-1-yl)-5-methylbenzene-κ²N³:N^3']] dihydrate] top

Crystal data top

[Cu(NO₃)₂(C₁₃H₁₂N₄)₂]·2H₂O	F(000) = 694
M_r = 672.12	D_x = 1.551 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4382 reflections
a = 11.585 (4) Å	θ = 2.6–26.1°
b = 9.652 (3) Å	µ = 0.83 mm⁻¹
c = 15.450 (4) Å	T = 293 K
β = 123.604 (17)°	Block, blue
V = 1438.9 (8) Å³	0.22 × 0.20 × 0.18 mm
Z = 2

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2672 independent reflections
Radiation source: sealed tube	2114 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
phi and ω scans	θ_max = 25.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→14
T_min = 0.839, T_max = 0.865	k = −11→11
10260 measured reflections	l = −18→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0393P)² + 1.4695P] where P = (F_o² + 2F_c²)/3
2672 reflections	(Δ/σ)_max = 0.002
214 parameters	Δρ_max = 0.43 e Å⁻³
2 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Cu(NO₃)₂(C₁₃H₁₂N₄)₂]·2H₂O	V = 1438.9 (8) Å³
M_r = 672.12	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.585 (4) Å	µ = 0.83 mm⁻¹
b = 9.652 (3) Å	T = 293 K
c = 15.450 (4) Å	0.22 × 0.20 × 0.18 mm
β = 123.604 (17)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2672 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2114 reflections with I > 2σ(I)
T_min = 0.839, T_max = 0.865	R_int = 0.039
10260 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	2 restraints
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.43 e Å⁻³
2672 reflections	Δρ_min = −0.51 e Å⁻³
214 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	0.0000	1.0000	0.5000	0.02941 (15)
N1	0.1444 (2)	0.9308 (2)	0.64001 (17)	0.0311 (5)
N2	0.2629 (2)	0.9008 (2)	0.80892 (16)	0.0283 (5)
N3	0.1879 (2)	1.1172 (2)	1.05555 (16)	0.0310 (5)
N4	0.0729 (2)	1.3057 (2)	1.04231 (17)	0.0333 (5)
N5	0.1839 (3)	0.9479 (3)	0.3683 (2)	0.0465 (6)
O1	0.1000 (3)	0.8849 (3)	0.28647 (19)	0.0649 (7)
O2	0.1663 (2)	0.9523 (3)	0.44070 (18)	0.0589 (6)
O3	0.2867 (4)	1.0002 (4)	0.3790 (3)	0.1209 (15)
O1W	0.5399 (4)	0.9268 (4)	0.3928 (3)	0.0902 (10)
C1	0.2547 (3)	0.8473 (3)	0.6687 (2)	0.0422 (7)
H1	0.2756	0.8095	0.6235	0.051*
C2	0.3288 (3)	0.8274 (3)	0.7721 (2)	0.0432 (7)
H2	0.4089	0.7745	0.8110	0.052*
C3	0.1522 (3)	0.9612 (3)	0.7259 (2)	0.0350 (6)
H3	0.0892	1.0172	0.7290	0.042*
C4	0.3023 (3)	0.9164 (3)	0.91399 (19)	0.0280 (6)
C5	0.4142 (3)	0.8449 (3)	0.9937 (2)	0.0316 (6)
H5	0.4639	0.7847	0.9791	0.038*
C6	0.4530 (3)	0.8625 (3)	1.0961 (2)	0.0309 (6)
C7	0.3782 (3)	0.9530 (3)	1.1169 (2)	0.0310 (6)
H7	0.4033	0.9667	1.1848	0.037*
C8	0.2661 (3)	1.0225 (2)	1.0358 (2)	0.0297 (6)
C9	0.2265 (3)	1.0052 (3)	0.9345 (2)	0.0305 (6)
H9	0.1502	1.0523	0.8808	0.037*
C10	0.5755 (3)	0.7855 (3)	1.1834 (2)	0.0436 (7)
H10A	0.6186	0.8405	1.2455	0.065*
H10B	0.6411	0.7676	1.1652	0.065*
H10C	0.5449	0.6993	1.1951	0.065*
C11	0.1473 (3)	1.2442 (3)	1.0130 (2)	0.0359 (6)
H11	0.1689	1.2832	0.9686	0.043*
C12	0.0659 (3)	1.2134 (3)	1.1069 (2)	0.0372 (6)
H12	0.0194	1.2287	1.1395	0.045*
C13	0.1364 (3)	1.0975 (3)	1.1159 (2)	0.0363 (6)
H13	0.1478	1.0195	1.1553	0.044*
H1WA	0.469 (3)	0.958 (4)	0.393 (3)	0.071 (14)*
H1WB	0.598 (5)	0.964 (5)	0.452 (2)	0.108 (19)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0332 (3)	0.0317 (3)	0.0254 (3)	−0.0040 (2)	0.0176 (2)	−0.00066 (19)
N1	0.0347 (12)	0.0316 (12)	0.0307 (12)	0.0004 (10)	0.0205 (10)	−0.0015 (10)
N2	0.0314 (12)	0.0295 (11)	0.0269 (11)	0.0031 (9)	0.0180 (10)	0.0017 (9)
N3	0.0381 (12)	0.0306 (12)	0.0301 (12)	0.0057 (10)	0.0225 (11)	0.0020 (9)
N4	0.0379 (13)	0.0343 (12)	0.0307 (12)	0.0047 (10)	0.0208 (11)	0.0004 (10)
N5	0.0402 (14)	0.0553 (16)	0.0518 (17)	0.0045 (13)	0.0302 (14)	0.0115 (14)
O1	0.0625 (16)	0.0795 (18)	0.0558 (15)	0.0080 (14)	0.0348 (14)	−0.0128 (14)
O2	0.0598 (15)	0.0764 (16)	0.0548 (15)	0.0019 (12)	0.0408 (13)	−0.0031 (12)
O3	0.087 (2)	0.180 (4)	0.112 (3)	−0.049 (2)	0.066 (2)	0.009 (2)
O1W	0.089 (3)	0.090 (2)	0.088 (3)	−0.026 (2)	0.047 (2)	−0.026 (2)
C1	0.0524 (18)	0.0464 (17)	0.0377 (16)	0.0166 (14)	0.0311 (15)	0.0048 (13)
C2	0.0470 (17)	0.0500 (18)	0.0392 (17)	0.0212 (14)	0.0280 (15)	0.0076 (14)
C3	0.0363 (15)	0.0385 (15)	0.0329 (15)	0.0069 (12)	0.0209 (13)	−0.0012 (12)
C4	0.0312 (13)	0.0284 (13)	0.0277 (13)	−0.0014 (11)	0.0184 (11)	0.0007 (10)
C5	0.0344 (14)	0.0268 (13)	0.0376 (15)	0.0031 (11)	0.0224 (13)	0.0007 (11)
C6	0.0321 (14)	0.0263 (13)	0.0328 (14)	−0.0008 (11)	0.0169 (12)	0.0026 (11)
C7	0.0374 (15)	0.0301 (13)	0.0264 (14)	−0.0017 (11)	0.0182 (12)	0.0015 (11)
C8	0.0355 (14)	0.0277 (14)	0.0315 (14)	0.0009 (11)	0.0221 (12)	0.0001 (10)
C9	0.0315 (13)	0.0314 (13)	0.0287 (14)	0.0056 (11)	0.0169 (11)	0.0045 (11)
C10	0.0428 (17)	0.0446 (17)	0.0368 (16)	0.0118 (14)	0.0179 (14)	0.0093 (13)
C11	0.0491 (17)	0.0350 (15)	0.0331 (15)	0.0073 (13)	0.0287 (14)	0.0060 (12)
C12	0.0446 (16)	0.0406 (16)	0.0371 (16)	0.0016 (13)	0.0294 (14)	0.0000 (12)
C13	0.0504 (17)	0.0342 (15)	0.0360 (15)	0.0020 (12)	0.0312 (14)	0.0049 (12)

Geometric parameters (Å, º) top

Cu1—N1	1.980 (2)	C1—H1	0.9300
Cu1—N1ⁱ	1.980 (2)	C2—H2	0.9300
Cu1—N4ⁱⁱ	2.011 (2)	C3—H3	0.9300
Cu1—N4ⁱⁱⁱ	2.011 (2)	C4—C5	1.381 (4)
N1—C3	1.313 (3)	C4—C9	1.383 (4)
N1—C1	1.360 (4)	C5—C6	1.395 (4)
N2—C3	1.345 (3)	C5—H5	0.9300
N2—C2	1.375 (3)	C6—C7	1.388 (4)
N2—C4	1.430 (3)	C6—C10	1.506 (4)
N3—C11	1.346 (3)	C7—C8	1.380 (4)
N3—C13	1.371 (3)	C7—H7	0.9300
N3—C8	1.434 (3)	C8—C9	1.376 (4)
N4—C11	1.316 (3)	C9—H9	0.9300
N4—C12	1.374 (3)	C10—H10A	0.9600
N4—Cu1^iv	2.011 (2)	C10—H10B	0.9600
N5—O3	1.217 (4)	C10—H10C	0.9600
N5—O2	1.244 (3)	C11—H11	0.9300
N5—O1	1.246 (4)	C12—C13	1.346 (4)
O1W—H1WA	0.877 (19)	C12—H12	0.9300
O1W—H1WB	0.86 (2)	C13—H13	0.9300
C1—C2	1.344 (4)

N1—Cu1—N1ⁱ	180.0	C5—C4—N2	120.8 (2)
N1—Cu1—N4ⁱⁱ	90.60 (9)	C9—C4—N2	118.7 (2)
N1ⁱ—Cu1—N4ⁱⁱ	89.40 (9)	C4—C5—C6	120.3 (2)
N1—Cu1—N4ⁱⁱⁱ	89.40 (9)	C4—C5—H5	119.8
N1ⁱ—Cu1—N4ⁱⁱⁱ	90.60 (9)	C6—C5—H5	119.8
N4ⁱⁱ—Cu1—N4ⁱⁱⁱ	180.0	C7—C6—C5	119.3 (2)
C3—N1—C1	106.1 (2)	C7—C6—C10	120.2 (2)
C3—N1—Cu1	124.95 (19)	C5—C6—C10	120.5 (2)
C1—N1—Cu1	128.98 (18)	C8—C7—C6	119.3 (2)
C3—N2—C2	106.5 (2)	C8—C7—H7	120.3
C3—N2—C4	125.0 (2)	C6—C7—H7	120.3
C2—N2—C4	128.5 (2)	C9—C8—C7	121.8 (2)
C11—N3—C13	107.0 (2)	C9—C8—N3	117.8 (2)
C11—N3—C8	124.6 (2)	C7—C8—N3	120.3 (2)
C13—N3—C8	128.3 (2)	C8—C9—C4	118.8 (2)
C11—N4—C12	105.7 (2)	C8—C9—H9	120.6
C11—N4—Cu1^iv	123.13 (18)	C4—C9—H9	120.6
C12—N4—Cu1^iv	131.13 (18)	C6—C10—H10A	109.5
O3—N5—O2	119.9 (3)	C6—C10—H10B	109.5
O3—N5—O1	119.7 (3)	H10A—C10—H10B	109.5
O2—N5—O1	120.3 (3)	C6—C10—H10C	109.5
H1WA—O1W—H1WB	92 (4)	H10A—C10—H10C	109.5
C2—C1—N1	109.8 (2)	H10B—C10—H10C	109.5
C2—C1—H1	125.1	N4—C11—N3	111.2 (2)
N1—C1—H1	125.1	N4—C11—H11	124.4
C1—C2—N2	106.4 (2)	N3—C11—H11	124.4
C1—C2—H2	126.8	C13—C12—N4	109.8 (2)
N2—C2—H2	126.8	C13—C12—H12	125.1
N1—C3—N2	111.3 (2)	N4—C12—H12	125.1
N1—C3—H3	124.4	C12—C13—N3	106.3 (2)
N2—C3—H3	124.4	C12—C13—H13	126.8
C5—C4—C9	120.5 (2)	N3—C13—H13	126.8

N1ⁱ—Cu1—N1—C3	−12 (3)	C4—C5—C6—C10	−179.6 (2)
N4ⁱⁱ—Cu1—N1—C3	66.7 (2)	C5—C6—C7—C8	0.7 (4)
N4ⁱⁱⁱ—Cu1—N1—C3	−113.3 (2)	C10—C6—C7—C8	−179.9 (3)
N1ⁱ—Cu1—N1—C1	170 (3)	C6—C7—C8—C9	−0.3 (4)
N4ⁱⁱ—Cu1—N1—C1	−111.9 (3)	C6—C7—C8—N3	−179.6 (2)
N4ⁱⁱⁱ—Cu1—N1—C1	68.1 (3)	C11—N3—C8—C9	−44.8 (4)
C3—N1—C1—C2	0.0 (3)	C13—N3—C8—C9	132.7 (3)
Cu1—N1—C1—C2	178.8 (2)	C11—N3—C8—C7	134.5 (3)
N1—C1—C2—N2	0.0 (4)	C13—N3—C8—C7	−48.0 (4)
C3—N2—C2—C1	0.1 (3)	C7—C8—C9—C4	−0.6 (4)
C4—N2—C2—C1	−178.3 (3)	N3—C8—C9—C4	178.7 (2)
C1—N1—C3—N2	0.1 (3)	C5—C4—C9—C8	1.1 (4)
Cu1—N1—C3—N2	−178.82 (17)	N2—C4—C9—C8	−178.6 (2)
C2—N2—C3—N1	−0.1 (3)	C12—N4—C11—N3	0.0 (3)
C4—N2—C3—N1	178.4 (2)	Cu1^iv—N4—C11—N3	177.32 (17)
C3—N2—C4—C5	176.8 (2)	C13—N3—C11—N4	−0.2 (3)
C2—N2—C4—C5	−5.1 (4)	C8—N3—C11—N4	177.7 (2)
C3—N2—C4—C9	−3.5 (4)	C11—N4—C12—C13	0.2 (3)
C2—N2—C4—C9	174.6 (3)	Cu1^iv—N4—C12—C13	−176.8 (2)
C9—C4—C5—C6	−0.7 (4)	N4—C12—C13—N3	−0.3 (3)
N2—C4—C5—C6	179.0 (2)	C11—N3—C13—C12	0.3 (3)
C4—C5—C6—C7	−0.2 (4)	C8—N3—C13—C12	−177.5 (3)

Symmetry codes: (i) −x, −y+2, −z+1; (ii) x, −y+5/2, z−1/2; (iii) −x, y−1/2, −z+3/2; (iv) −x, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3	0.88 (2)	2.04 (2)	2.909 (6)	170 (4)
O1W—H1WB···O3^v	0.86 (2)	2.20 (3)	3.020 (5)	159 (5)
O1W—H1WB···O2^v	0.86 (2)	2.42 (4)	3.142 (4)	142 (5)
C2—H2···O1W^vi	0.93	2.36	3.230 (5)	156
C3—H3···O1ⁱ	0.93	2.27	3.186 (4)	167

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

Experimental details

Crystal data
Chemical formula	[Cu(NO₃)₂(C₁₃H₁₂N₄)₂]·2H₂O
M_r	672.12
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.585 (4), 9.652 (3), 15.450 (4)
β (°)	123.604 (17)
V (Å³)	1438.9 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.83
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.839, 0.865
No. of measured, independent and observed [I > 2σ(I)] reflections	10260, 2672, 2114
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.101, 1.06
No. of reflections	2672
No. of parameters	214
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.51

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), 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
O1W—H1WA···O3	0.88 (2)	2.04 (2)	2.909 (6)	170 (4)
O1W—H1WB···O3ⁱ	0.86 (2)	2.20 (3)	3.020 (5)	159 (5)
O1W—H1WB···O2ⁱ	0.86 (2)	2.42 (4)	3.142 (4)	142 (5)
C2—H2···O1Wⁱⁱ	0.93	2.36	3.230 (5)	156
C3—H3···O1ⁱⁱⁱ	0.93	2.27	3.186 (4)	167

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, −y+3/2, z+1/2; (iii) −x, −y+2, −z+1.

Acknowledgements

This work was supported by the Natural Science Foundation of Anhui Province (No. KJ2012A204).

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