Nitrato(1,10-phenanthroline)(1H-1,2,4-triazole-3-carboxyl­ato)copper(II)

Zhu, J.; Yin, X.-H.; Wei, Y.-Y.; Qin, R.-W.; Lin, C.-W.; Nong, H.-F.

doi:10.1107/S1600536808001803

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m392

doi:10.1107/S1600536808001803

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Nitrato(1,10-phenanthroline)(1H-1,2,4-triazole-3-carboxylato)copper(II)

Jie Zhu,^a,^b Xian-Hong Yin,^a,^b ^* Ya-Yan Wei,^a Ru-Wen Qin,^a Cui-Wu Lin ^b and Hong-Feng Nong ^a

^aCollege of Chemistry and Ecological Engineering, Guangxi University for Nationalities, Nanning 530006, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, People's Republic of China
^*Correspondence e-mail: yxhphd@163.com

(Received 13 January 2008; accepted 17 January 2008; online 23 January 2008)

In the title complex, [Cu(C₃H₂N₃O₂)(NO₃)(C₁₂H₈N₂)], the Cu^II ion is coordinated by an N and an O atom from a bidentate 1H-1,2,4-triazole-3-carboxylate (TRIA) ligand, two N atoms from a 1,10-phenanthroline (phen) ligand, and an O atom from a nitrate ligand in a slightly distorted square-pyramidal environment. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link molecules into one-dimensional chains propagating along the b axis direction.

Related literature

For related literature, see: Guo & Wang (2005 ); Zhu et al. (2007 ); Zhu, Yin, Feng, Zhang et al. (2008 ); Zhu, Yin, Feng, Hu et al. (2008 ).

Experimental

Crystal data

[Cu(C₃H₂N₃O₂)(NO₃)(C₁₂H₈N₂)]
M_r = 417.83
Monoclinic, P 2₁ /c
a = 12.3779 (14) Å
b = 12.6444 (15) Å
c = 10.0196 (10) Å
β = 107.416 (2)°
V = 1496.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.51 mm⁻¹
T = 298 (2) K
0.34 × 0.30 × 0.25 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.628, T_max = 0.704
7489 measured reflections
2601 independent reflections
2102 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.086
S = 1.06
2601 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.9540 (19)
Cu1—N4	1.988 (2)
Cu1—N3	2.005 (2)
Cu1—N5	2.015 (2)
Cu1—O3	2.315 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	1.92	2.775 (3)	172
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808001803/lh2590sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808001803/lh2590Isup2.hkl

checkCIF report

Comment top

In connection with our on-going studies in coordination chemistry (Zhu et al., 2007; Zhu, Yin, Feng, Hu et al., 2008; Zhu, Yin, Feng, Zhang et al., 2008) and the biological importance of triazole molecules (Guo et al., 2005), the crystal structure of a new ternary Cu(II) complex with 1H-1,2,4-triazole-3-carboxylate (TRIA), 1,10-phenanthroline (phen) and NO₃ ligands is described. The molecular structure of the title compound is shown in Fig. 1. The Cu^II ion is bis-chelated by an N and an O atom, from a TRIA ligand, two N atoms from the chelating phen ligand, and the coordination geometry is completed by a O atom from an NO₃ ligand. The atom O3 from the NO₃ ligand occupies the apical site in a slightly distorted square-pyramidal ON₃O coordination environment. The primary intermolecular contacts in the crystal structure are of the type N—H···O and involve the non-coordinating O atom of the carbonyl group and the N—H group of the TRIA ligand.

Related literature top

For related literature, see: Guo & Wang (2005); Zhu et al. (2007); Zhu, Yin, Feng, Zhang et al. (2008); Zhu, Yin, Feng, Hu et al. (2008).

Experimental top

CuNO₃.3H₂O (0.5 mmol, 120.8 mg) dissolved in distilled water (5 ml) was added with stirring at 323 K to 1H-1,2,4-triazole-3-carboxylic acid (0.5 mmol, 56.5 mg) also dissolved in distilled water (15 ml). The resulting blue solution was allowed to react for 30 min and 1,10-phenanthroline (0.5 mmol, 99.1 mg) dissolved in ethanol (5 ml) was added. Dark-blue crystals suitable for X-ray analysis were obtained by slow evaporation over a period of one month (yield 55%). Analysis. Found: C 43.28, H 2.22, N 20.33, O 19.01%. C₁₅H₁₀CuN₆O₅ requires: C 43.12, H 2.41, N 20.11, O 19.15%.

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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Part of the crystal structure of the title compound showing hydrogen bonds as dashed lines.

Nitrato(1,10-phenanthroline)(1H-1,2,4-triazole-3-carboxylato)copper(II) top

Crystal data top

[Cu(C₃H₂N₃O₂)(NO₃)(C₁₂H₈N₂)]	F(000) = 844
M_r = 417.83	D_x = 1.855 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3888 reflections
a = 12.3779 (14) Å	θ = 2.7–27.7°
b = 12.6444 (15) Å	µ = 1.51 mm⁻¹
c = 10.0196 (10) Å	T = 298 K
β = 107.416 (2)°	Block, dark-blue
V = 1496.3 (3) Å³	0.34 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2601 independent reflections
Radiation source: fine-focus sealed tube	2102 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→8
T_min = 0.628, T_max = 0.704	k = −14→15
7489 measured reflections	l = −11→11

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0436P)² + 0.8762P] where P = (F_o² + 2F_c²)/3
2601 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Cu(C₃H₂N₃O₂)(NO₃)(C₁₂H₈N₂)]	V = 1496.3 (3) Å³
M_r = 417.83	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3779 (14) Å	µ = 1.51 mm⁻¹
b = 12.6444 (15) Å	T = 298 K
c = 10.0196 (10) Å	0.34 × 0.30 × 0.25 mm
β = 107.416 (2)°

Data collection top

Bruker SMART CCD diffractometer	2601 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2102 reflections with I > 2σ(I)
T_min = 0.628, T_max = 0.704	R_int = 0.033
7489 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.06	Δρ_max = 0.31 e Å⁻³
2601 reflections	Δρ_min = −0.29 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	0.67882 (3)	1.02713 (2)	0.58353 (3)	0.02944 (14)
N1	0.57639 (19)	1.32426 (17)	0.6760 (2)	0.0321 (5)
H1	0.5704	1.3918	0.6815	0.039*
N2	0.52709 (19)	1.25284 (17)	0.7412 (2)	0.0309 (5)
N3	0.62666 (18)	1.17198 (17)	0.6177 (2)	0.0279 (5)
N4	0.69970 (18)	0.87706 (17)	0.5374 (2)	0.0277 (5)
N5	0.78098 (19)	1.05325 (17)	0.4636 (2)	0.0298 (5)
N6	0.8485 (2)	1.07924 (19)	0.8885 (2)	0.0360 (6)
O1	0.56644 (17)	0.98205 (14)	0.6733 (2)	0.0369 (5)
O2	0.46508 (19)	1.03880 (15)	0.8074 (2)	0.0449 (6)
O3	0.83942 (18)	1.03049 (17)	0.7753 (2)	0.0451 (5)
O4	0.76459 (19)	1.08825 (19)	0.9301 (2)	0.0512 (6)
O5	0.9405 (2)	1.1152 (2)	0.9554 (3)	0.0639 (7)
C1	0.5273 (2)	1.0534 (2)	0.7344 (3)	0.0304 (6)
C2	0.5598 (2)	1.1626 (2)	0.7031 (3)	0.0268 (6)
C3	0.6344 (2)	1.2759 (2)	0.6036 (3)	0.0315 (6)
H3	0.6746	1.3093	0.5507	0.038*
C4	0.6555 (2)	0.7905 (2)	0.5753 (3)	0.0312 (6)
H4A	0.6063	0.7972	0.6290	0.037*
C5	0.6811 (2)	0.6898 (2)	0.5364 (3)	0.0355 (7)
H5A	0.6479	0.6306	0.5629	0.043*
C6	0.7544 (2)	0.6778 (2)	0.4597 (3)	0.0367 (7)
H6	0.7714	0.6107	0.4336	0.044*
C7	0.8041 (2)	0.7676 (2)	0.4206 (3)	0.0300 (6)
C8	0.7725 (2)	0.8658 (2)	0.4602 (3)	0.0255 (6)
C9	0.8155 (2)	0.9609 (2)	0.4195 (2)	0.0261 (6)
C10	0.8887 (2)	0.9563 (2)	0.3374 (3)	0.0314 (6)
C11	0.9255 (3)	1.0523 (3)	0.2966 (3)	0.0403 (7)
H11	0.9718	1.0534	0.2387	0.048*
C12	0.8919 (3)	1.1448 (2)	0.3435 (3)	0.0427 (8)
H12	0.9169	1.2092	0.3190	0.051*
C13	0.8209 (2)	1.1429 (2)	0.4275 (3)	0.0375 (7)
H13	0.8005	1.2066	0.4597	0.045*
C14	0.8817 (2)	0.7653 (2)	0.3406 (3)	0.0371 (7)
H14	0.9051	0.7004	0.3153	0.044*
C15	0.9220 (2)	0.8549 (2)	0.3007 (3)	0.0368 (7)
H15	0.9725	0.8508	0.2483	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0405 (2)	0.01967 (19)	0.0373 (2)	−0.00062 (14)	0.02555 (16)	−0.00268 (14)
N1	0.0420 (14)	0.0163 (11)	0.0440 (13)	0.0013 (10)	0.0220 (12)	−0.0007 (10)
N2	0.0386 (13)	0.0201 (11)	0.0407 (13)	0.0001 (10)	0.0221 (11)	0.0015 (10)
N3	0.0353 (13)	0.0223 (11)	0.0327 (12)	−0.0008 (9)	0.0202 (10)	−0.0008 (9)
N4	0.0314 (12)	0.0261 (12)	0.0292 (11)	−0.0020 (10)	0.0146 (10)	−0.0007 (10)
N5	0.0370 (13)	0.0252 (12)	0.0329 (12)	−0.0017 (10)	0.0190 (11)	−0.0019 (10)
N6	0.0483 (16)	0.0258 (12)	0.0368 (14)	−0.0026 (11)	0.0172 (13)	0.0039 (11)
O1	0.0511 (13)	0.0207 (10)	0.0525 (12)	−0.0022 (8)	0.0361 (11)	−0.0036 (9)
O2	0.0627 (15)	0.0243 (11)	0.0683 (14)	0.0007 (9)	0.0509 (12)	0.0013 (10)
O3	0.0444 (13)	0.0571 (15)	0.0368 (11)	0.0069 (10)	0.0165 (10)	−0.0106 (10)
O4	0.0593 (15)	0.0496 (14)	0.0559 (14)	0.0053 (11)	0.0343 (12)	−0.0101 (11)
O5	0.0640 (17)	0.0648 (17)	0.0596 (15)	−0.0248 (14)	0.0132 (13)	−0.0089 (13)
C1	0.0362 (16)	0.0225 (13)	0.0379 (15)	0.0015 (11)	0.0194 (13)	0.0012 (12)
C2	0.0298 (14)	0.0226 (14)	0.0310 (14)	0.0013 (11)	0.0140 (12)	−0.0009 (11)
C3	0.0387 (16)	0.0241 (14)	0.0367 (15)	−0.0015 (12)	0.0189 (13)	0.0011 (12)
C4	0.0370 (16)	0.0276 (14)	0.0306 (14)	−0.0006 (12)	0.0129 (13)	0.0009 (11)
C5	0.0420 (17)	0.0244 (14)	0.0406 (16)	−0.0032 (12)	0.0134 (14)	0.0017 (12)
C6	0.0425 (18)	0.0239 (14)	0.0427 (16)	0.0052 (12)	0.0109 (14)	−0.0039 (12)
C7	0.0340 (15)	0.0281 (15)	0.0292 (14)	0.0029 (12)	0.0112 (12)	−0.0035 (11)
C8	0.0267 (14)	0.0271 (14)	0.0237 (13)	0.0011 (11)	0.0090 (11)	−0.0028 (11)
C9	0.0290 (14)	0.0270 (14)	0.0243 (13)	0.0001 (11)	0.0109 (11)	−0.0019 (11)
C10	0.0284 (15)	0.0396 (17)	0.0291 (14)	−0.0008 (12)	0.0130 (12)	−0.0023 (12)
C11	0.0413 (18)	0.0448 (19)	0.0421 (17)	−0.0041 (14)	0.0237 (15)	0.0021 (14)
C12	0.0499 (19)	0.0366 (17)	0.0524 (19)	−0.0053 (14)	0.0319 (16)	0.0055 (14)
C13	0.0464 (18)	0.0246 (15)	0.0483 (18)	−0.0022 (12)	0.0245 (15)	−0.0018 (13)
C14	0.0417 (17)	0.0338 (16)	0.0390 (16)	0.0071 (13)	0.0169 (14)	−0.0092 (13)
C15	0.0340 (16)	0.0440 (18)	0.0389 (16)	0.0040 (13)	0.0207 (13)	−0.0072 (13)

Geometric parameters (Å, º) top

Cu1—O1	1.9540 (19)	C3—H3	0.9300
Cu1—N4	1.988 (2)	C4—C5	1.396 (4)
Cu1—N3	2.005 (2)	C4—H4A	0.9300
Cu1—N5	2.015 (2)	C5—C6	1.362 (4)
Cu1—O3	2.315 (2)	C5—H5A	0.9300
N1—C3	1.314 (3)	C6—C7	1.402 (4)
N1—N2	1.361 (3)	C6—H6	0.9300
N1—H1	0.8600	C7—C8	1.395 (4)
N2—C2	1.305 (3)	C7—C14	1.424 (4)
N3—C3	1.329 (3)	C8—C9	1.423 (4)
N3—C2	1.363 (3)	C9—C10	1.396 (4)
N4—C4	1.329 (3)	C10—C11	1.401 (4)
N4—C8	1.359 (3)	C10—C15	1.427 (4)
N5—C13	1.329 (4)	C11—C12	1.371 (4)
N5—C9	1.362 (3)	C11—H11	0.9300
N6—O5	1.223 (3)	C12—C13	1.387 (4)
N6—O4	1.234 (3)	C12—H12	0.9300
N6—O3	1.267 (3)	C13—H13	0.9300
O1—C1	1.266 (3)	C14—C15	1.347 (4)
O2—C1	1.225 (3)	C14—H14	0.9300
C1—C2	1.497 (4)	C15—H15	0.9300

O1—Cu1—N4	89.34 (8)	N4—C4—C5	121.7 (3)
O1—Cu1—N3	82.99 (8)	N4—C4—H4A	119.2
N4—Cu1—N3	169.22 (9)	C5—C4—H4A	119.2
O1—Cu1—N5	169.26 (8)	C6—C5—C4	120.3 (3)
N4—Cu1—N5	82.50 (9)	C6—C5—H5A	119.9
N3—Cu1—N5	104.10 (9)	C4—C5—H5A	119.9
O1—Cu1—O3	100.15 (8)	C5—C6—C7	119.3 (3)
N4—Cu1—O3	94.09 (8)	C5—C6—H6	120.3
N3—Cu1—O3	94.71 (8)	C7—C6—H6	120.3
N5—Cu1—O3	87.45 (8)	C8—C7—C6	117.2 (2)
C3—N1—N2	110.7 (2)	C8—C7—C14	118.2 (3)
C3—N1—H1	124.6	C6—C7—C14	124.5 (3)
N2—N1—H1	124.6	N4—C8—C7	123.0 (2)
C2—N2—N1	102.5 (2)	N4—C8—C9	116.3 (2)
C3—N3—C2	103.2 (2)	C7—C8—C9	120.6 (2)
C3—N3—Cu1	148.06 (19)	N5—C9—C10	123.3 (2)
C2—N3—Cu1	108.37 (16)	N5—C9—C8	116.8 (2)
C4—N4—C8	118.4 (2)	C10—C9—C8	119.9 (2)
C4—N4—Cu1	128.81 (18)	C9—C10—C11	117.4 (3)
C8—N4—Cu1	112.74 (17)	C9—C10—C15	118.6 (3)
C13—N5—C9	117.7 (2)	C11—C10—C15	124.0 (3)
C13—N5—Cu1	130.77 (19)	C12—C11—C10	118.8 (3)
C9—N5—Cu1	111.51 (17)	C12—C11—H11	120.6
O5—N6—O4	121.3 (3)	C10—C11—H11	120.6
O5—N6—O3	119.4 (3)	C11—C12—C13	120.3 (3)
O4—N6—O3	119.3 (2)	C11—C12—H12	119.8
C1—O1—Cu1	116.28 (17)	C13—C12—H12	119.8
N6—O3—Cu1	125.19 (17)	N5—C13—C12	122.4 (3)
O2—C1—O1	125.5 (2)	N5—C13—H13	118.8
O2—C1—C2	121.4 (2)	C12—C13—H13	118.8
O1—C1—C2	113.0 (2)	C15—C14—C7	121.5 (3)
N2—C2—N3	114.1 (2)	C15—C14—H14	119.3
N2—C2—C1	128.3 (2)	C7—C14—H14	119.3
N3—C2—C1	117.6 (2)	C14—C15—C10	121.2 (3)
N1—C3—N3	109.4 (2)	C14—C15—H15	119.4
N1—C3—H3	125.3	C10—C15—H15	119.4
N3—C3—H3	125.3

C3—N1—N2—C2	0.2 (3)	O1—C1—C2—N2	174.8 (3)
O1—Cu1—N3—C3	−178.1 (4)	O2—C1—C2—N3	−178.1 (3)
N4—Cu1—N3—C3	−133.1 (5)	O1—C1—C2—N3	−1.0 (4)
N5—Cu1—N3—C3	−6.3 (4)	N2—N1—C3—N3	−0.2 (3)
O3—Cu1—N3—C3	82.3 (4)	C2—N3—C3—N1	0.2 (3)
O1—Cu1—N3—C2	10.49 (17)	Cu1—N3—C3—N1	−171.5 (3)
N4—Cu1—N3—C2	55.4 (5)	C8—N4—C4—C5	−0.7 (4)
N5—Cu1—N3—C2	−177.73 (17)	Cu1—N4—C4—C5	−178.4 (2)
O3—Cu1—N3—C2	−89.18 (18)	N4—C4—C5—C6	1.1 (4)
O1—Cu1—N4—C4	−5.8 (2)	C4—C5—C6—C7	0.1 (4)
N3—Cu1—N4—C4	−50.4 (6)	C5—C6—C7—C8	−1.7 (4)
N5—Cu1—N4—C4	−178.8 (2)	C5—C6—C7—C14	−179.9 (3)
O3—Cu1—N4—C4	94.3 (2)	C4—N4—C8—C7	−0.9 (4)
O1—Cu1—N4—C8	176.37 (18)	Cu1—N4—C8—C7	177.13 (19)
N3—Cu1—N4—C8	131.8 (4)	C4—N4—C8—C9	178.6 (2)
N5—Cu1—N4—C8	3.38 (17)	Cu1—N4—C8—C9	−3.4 (3)
O3—Cu1—N4—C8	−83.50 (18)	C6—C7—C8—N4	2.1 (4)
O1—Cu1—N5—C13	139.0 (4)	C14—C7—C8—N4	−179.5 (2)
N4—Cu1—N5—C13	179.9 (3)	C6—C7—C8—C9	−177.4 (2)
N3—Cu1—N5—C13	8.6 (3)	C14—C7—C8—C9	1.0 (4)
O3—Cu1—N5—C13	−85.6 (3)	C13—N5—C9—C10	−0.9 (4)
O1—Cu1—N5—C9	−43.7 (5)	Cu1—N5—C9—C10	−178.6 (2)
N4—Cu1—N5—C9	−2.82 (17)	C13—N5—C9—C8	179.5 (2)
N3—Cu1—N5—C9	−174.14 (17)	Cu1—N5—C9—C8	1.8 (3)
O3—Cu1—N5—C9	91.65 (18)	N4—C8—C9—N5	1.0 (3)
N4—Cu1—O1—C1	175.3 (2)	C7—C8—C9—N5	−179.5 (2)
N3—Cu1—O1—C1	−12.3 (2)	N4—C8—C9—C10	−178.6 (2)
N5—Cu1—O1—C1	−144.3 (4)	C7—C8—C9—C10	0.9 (4)
O3—Cu1—O1—C1	81.2 (2)	N5—C9—C10—C11	−1.6 (4)
O5—N6—O3—Cu1	−148.4 (2)	C8—C9—C10—C11	178.0 (2)
O4—N6—O3—Cu1	32.6 (3)	N5—C9—C10—C15	178.1 (2)
O1—Cu1—O3—N6	−52.7 (2)	C8—C9—C10—C15	−2.3 (4)
N4—Cu1—O3—N6	−142.7 (2)	C9—C10—C11—C12	2.6 (4)
N3—Cu1—O3—N6	31.0 (2)	C15—C10—C11—C12	−177.0 (3)
N5—Cu1—O3—N6	135.0 (2)	C10—C11—C12—C13	−1.3 (5)
Cu1—O1—C1—O2	−172.5 (2)	C9—N5—C13—C12	2.4 (4)
Cu1—O1—C1—C2	10.6 (3)	Cu1—N5—C13—C12	179.5 (2)
N1—N2—C2—N3	−0.1 (3)	C11—C12—C13—N5	−1.3 (5)
N1—N2—C2—C1	−176.0 (3)	C8—C7—C14—C15	−1.6 (4)
C3—N3—C2—N2	0.0 (3)	C6—C7—C14—C15	176.7 (3)
Cu1—N3—C2—N2	175.33 (18)	C7—C14—C15—C10	0.2 (4)
C3—N3—C2—C1	176.3 (2)	C9—C10—C15—C14	1.8 (4)
Cu1—N3—C2—C1	−8.3 (3)	C11—C10—C15—C14	−178.5 (3)
O2—C1—C2—N2	−2.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	1.92	2.775 (3)	172

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Cu(C₃H₂N₃O₂)(NO₃)(C₁₂H₈N₂)]
M_r	417.83
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.3779 (14), 12.6444 (15), 10.0196 (10)
β (°)	107.416 (2)
V (Å³)	1496.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.51
Crystal size (mm)	0.34 × 0.30 × 0.25

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.628, 0.704
No. of measured, independent and observed [I > 2σ(I)] reflections	7489, 2601, 2102
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.086, 1.06
No. of reflections	2601
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.29

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O1	1.9540 (19)	Cu1—N5	2.015 (2)
Cu1—N4	1.988 (2)	Cu1—O3	2.315 (2)
Cu1—N3	2.005 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	1.92	2.775 (3)	171.8

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant No. 20761002). This research was also sponsored by the Talented Highland Research Programme of Guangxi University, the Science Foundation of the State Ethnic Affairs Commission (grant No. 07GX05), the Development Foundation Guangxi Research Institute of Chemical Industry, the Ministry of Education, Science and Technology Key Projects (grant No. 205121), and the Science Foundation of Guangxi University for Nationalities (grant Nos. 0409032, 0409012, 0509ZD047), People's Republic of China.

References

Guo, X.-H. & Wang, Q.-X. (2005). Acta Cryst. E61, o3217–o3218. Web of Science CSD CrossRef IUCr Journals 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
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhu, J., Yin, X.-H., Feng, Y., Hu, F.-L., Zhuang, Y. & Lin, C.-W. (2008). Acta Cryst. E64, m119. Web of Science CSD CrossRef IUCr Journals Google Scholar
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