Aqua­(2-hydrazino-1,10-phenanthroline)nitratocopper(II) nitrate

Li, H.L.; Liu, Q.S.

doi:10.1107/S1600536808015523

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page m847

doi:10.1107/S1600536808015523

Open

access

Aqua(2-hydrazino-1,10-phenanthroline)nitratocopper(II) nitrate

Hong Liang Li ^a ^* and Qi Sheng Liu ^b

^aDepartment of Chemistry, Dezhou University, Dezhou Shandong 253023, People's Republic of China, and ^bDepartment of Chemistry, Shandong Normal University, Jinan 250014, People's Republic of China
^*Correspondence e-mail: hongliangl1968@yahoo.com.cn

(Received 16 May 2008; accepted 22 May 2008; online 30 May 2008)

In the title mononuclear complex, [Cu(NO₃)(C₁₂H₁₀N₄)(H₂O)]NO₃, the Cu^II ion assumes a distorted square-pyramidal geometry. There is a π–π stacking interaction between the five-membered ring containing the Cu atom and a pyridine ring of a neighboring complex [centroid–centroid distance = 3.567 (2) Å and a perpendicular distance of 3.394 Å]. The crystal structure also contains intermolecular N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds, linking cations and anions. In addition, there is a short intermolecular contact [2.784 (6) Å] between an O atom of the coordinated nitrate group and its symmetry-related atom.

Related literature

For related structures, see: Liu et al. (2008 ); Lewis et al. (1980 ).

Experimental

Crystal data

[Cu(NO₃)(C₁₂H₁₀N₄)(H₂O)]NO₃
M_r = 415.82
Monoclinic, P 2₁ /n
a = 8.7175 (8) Å
b = 10.7746 (10) Å
c = 16.4725 (16) Å
β = 97.175 (2)°
V = 1535.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.48 mm⁻¹
T = 298 (2) K
0.50 × 0.20 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.525, T_max = 0.843
8857 measured reflections
3329 independent reflections
2735 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.112
S = 1.03
3329 reflections
235 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6ⁱ	0.86	2.18	2.936 (4)	146
N1—H1⋯O7ⁱ	0.86	2.54	3.181 (4)	132
N2—H2A⋯O3ⁱⁱ	0.90	2.22	3.111 (4)	169
N2—H2B⋯O7ⁱⁱⁱ	0.90	2.17	3.055 (4)	168
O1—H9⋯O5ⁱⁱⁱ	0.84	1.98	2.818 (3)	175
O1—H9⋯O7ⁱⁱⁱ	0.84	2.58	3.185 (3)	130
O1—H13⋯O6^iv	0.85	1.99	2.821 (3)	167
C2—H2⋯O6ⁱ	0.93	2.56	3.253 (4)	132
C3—H3⋯O1^v	0.93	2.48	3.280 (4)	144
C11—H11⋯O4^vi	0.93	2.43	3.118 (5)	131
Symmetry codes: (i) x-1, y, z-1; (ii) -x+1, -y, -z; (iii) -x+1, -y, -z+1; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) -x, -y+1, -z; (vi) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808015523/wn2264sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015523/wn2264Isup2.hkl

checkCIF report

Comment top

Derivatives of 1,10-phenanthroline play an important role in modern coordination chemistry (Liu et al., 2008), and although complexes with 2,9-dihydrazino-1,10-phenanthroline as ligand have been published (Lewis et al., 1980), to the best of our knowledge, no crystal structure of the title complex has been published.

Fig. 1 shows the structure, revealing that the Cu atom is in a distorted square-pyramidal environment, with atom O1 in the apical position. There is a single π-π stacking interaction involving symmetry-related 1,10-phenanthroline ligands, the relevant distances being Cg1···Cg2^v = 3.567 (2) Å and Cg1···Cg2^v_perp = 3.394 Å and α = 3.76° [symmetry code: (v) -x, 1 - y, -z; Cg1 and Cg2 are the centroids of the Cu1/N5/N6/C8/C9 ring and N6/C7/C8/C10-C12 ring, respectively; Cg1···Cg2¹_perp is the perpendicular distance from ring Cg1 to ring Cg2ⁱ; α is the dihedral angle between ring plane Cg1 and ring plane Cg2ⁱ]. There exists a short contact [2.784 (6) Å] between atom O3 and its symmetry-related atom O3ⁱⁱ [symmetry code: (ii) 1-x,-y,-z], as shown in Fig. 2 (double dashed lines). In addition, the crystal structure contains classical N—H..O and O—H···O hydrogen bonds, also non-classical C—H···O hydrogen bonds, as shown in Table 1 and Fig. 2. The π-π stacking interaction, the short contact between atom O3 and its symmetry-related atom O3ⁱⁱ and the hydrogen bonds stabilize the crystal structure.

Related literature top

For related structures, see: Liu et al. (2008); Lewis et al. (1980).

Experimental top

10 ml methanol solution of 2-hydrazino-1,10-phenanthroline (0.0105 g, 0.0576 mmol) was added to 5 ml aqueous solution of Cu(NO₃)₂.3H₂O (0.0390 g, 0.161 mmol) and the mixture was stirred for a few minutes. Deep-green single crystals were obtained after the filtrate had been allowed to stand at room temperature for two weeks.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

	Fig. 1. Structure of the title complex with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the packing in the crystal structure. Short contacts between atom O3 and its symmetry-related atoms are shown as double dashed lines and hydrogen bonds as dashed lines.

Aqua(2-hydrazino-1,10-phenanthroline)nitratocopper(II) nitrate top

Crystal data top

[Cu(NO₃)(C₁₂H₁₀N₄)(H₂O)]NO₃	F(000) = 844
M_r = 415.82	D_x = 1.799 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2442 reflections
a = 8.7175 (8) Å	θ = 2.3–24.6°
b = 10.7746 (10) Å	µ = 1.48 mm⁻¹
c = 16.4725 (16) Å	T = 298 K
β = 97.175 (2)°	Block, green
V = 1535.1 (2) Å³	0.50 × 0.20 × 0.12 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3329 independent reflections
Radiation source: fine-focus sealed tube	2735 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.525, T_max = 0.843	k = −13→13
8857 measured reflections	l = −12→20

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.058P)² + 0.4576P] where P = (F_o² + 2F_c²)/3
3329 reflections	(Δ/σ)_max = 0.002
235 parameters	Δρ_max = 0.70 e Å⁻³
3 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Cu(NO₃)(C₁₂H₁₀N₄)(H₂O)]NO₃	V = 1535.1 (2) Å³
M_r = 415.82	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.7175 (8) Å	µ = 1.48 mm⁻¹
b = 10.7746 (10) Å	T = 298 K
c = 16.4725 (16) Å	0.50 × 0.20 × 0.12 mm
β = 97.175 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	3329 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2735 reflections with I > 2σ(I)
T_min = 0.525, T_max = 0.843	R_int = 0.034
8857 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	3 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	Δρ_max = 0.70 e Å⁻³
3329 reflections	Δρ_min = −0.33 e Å⁻³
235 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
C1	0.1553 (4)	0.3275 (3)	−0.07122 (17)	0.0395 (7)
C2	0.0545 (4)	0.3975 (3)	−0.12818 (19)	0.0478 (8)
H2	−0.0080	0.3581	−0.1704	0.057*
C3	0.0507 (4)	0.5226 (3)	−0.1201 (2)	0.0492 (8)
H3	−0.0159	0.5689	−0.1568	0.059*
C4	0.1460 (4)	0.5839 (3)	−0.05691 (19)	0.0441 (8)
C5	0.1525 (5)	0.7152 (3)	−0.0411 (2)	0.0539 (9)
H5	0.0886	0.7683	−0.0745	0.065*
C6	0.2498 (4)	0.7624 (3)	0.0215 (2)	0.0541 (9)
H6	0.2504	0.8477	0.0302	0.065*
C7	0.3518 (4)	0.6866 (3)	0.0746 (2)	0.0459 (8)
C8	0.3481 (3)	0.5572 (3)	0.06060 (17)	0.0377 (7)
C9	0.2440 (3)	0.5098 (3)	−0.00470 (18)	0.0364 (6)
C10	0.5401 (4)	0.5172 (3)	0.1667 (2)	0.0462 (8)
H10	0.6058	0.4620	0.1974	0.055*
C11	0.5497 (4)	0.6440 (3)	0.1859 (2)	0.0550 (9)
H11	0.6190	0.6713	0.2297	0.066*
C12	0.4578 (5)	0.7272 (3)	0.1405 (2)	0.0548 (9)
H12	0.4653	0.8113	0.1533	0.066*
Cu1	0.37741 (4)	0.29261 (3)	0.06801 (2)	0.03598 (14)
N1	0.1698 (3)	0.2036 (2)	−0.07207 (16)	0.0478 (7)
H1	0.1211	0.1587	−0.1101	0.057*
N2	0.2703 (3)	0.1510 (2)	−0.00644 (15)	0.0432 (6)
H2A	0.3427	0.1045	−0.0265	0.052*
H2B	0.2160	0.1014	0.0235	0.052*
N3	0.5836 (3)	0.1007 (3)	0.13379 (17)	0.0499 (7)
N4	0.8613 (3)	0.0304 (2)	0.83090 (17)	0.0472 (7)
N5	0.2458 (3)	0.3843 (2)	−0.01228 (14)	0.0362 (5)
N6	0.4397 (3)	0.4735 (2)	0.10578 (15)	0.0376 (5)
O1	0.2264 (3)	0.27432 (18)	0.16726 (12)	0.0440 (5)
H9	0.2273	0.1980	0.1784	0.066*
H13	0.2717	0.3128	0.2083	0.066*
O2	0.5464 (3)	0.21509 (19)	0.13917 (15)	0.0516 (6)
O3	0.5139 (4)	0.0349 (2)	0.08196 (18)	0.0770 (9)
O4	0.6890 (4)	0.0598 (3)	0.1787 (2)	0.1068 (13)
O5	0.7508 (3)	−0.0211 (2)	0.79020 (18)	0.0735 (8)
O6	0.9063 (3)	0.1324 (2)	0.80827 (14)	0.0610 (7)
O7	0.9290 (3)	−0.0178 (2)	0.89371 (16)	0.0627 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0392 (17)	0.0383 (16)	0.0423 (17)	0.0019 (13)	0.0106 (13)	0.0020 (13)
C2	0.0441 (19)	0.052 (2)	0.0457 (18)	0.0053 (15)	0.0008 (14)	0.0062 (15)
C3	0.0418 (19)	0.057 (2)	0.0492 (19)	0.0118 (16)	0.0085 (15)	0.0152 (16)
C4	0.0469 (19)	0.0369 (16)	0.0527 (19)	0.0104 (14)	0.0224 (15)	0.0106 (13)
C5	0.063 (2)	0.0395 (18)	0.062 (2)	0.0131 (16)	0.0210 (18)	0.0150 (16)
C6	0.071 (3)	0.0282 (16)	0.069 (2)	0.0072 (16)	0.034 (2)	0.0047 (15)
C7	0.058 (2)	0.0293 (15)	0.056 (2)	−0.0025 (14)	0.0284 (17)	−0.0018 (13)
C8	0.0413 (17)	0.0320 (15)	0.0436 (16)	−0.0005 (12)	0.0199 (13)	0.0007 (12)
C9	0.0404 (17)	0.0297 (14)	0.0416 (16)	0.0044 (12)	0.0149 (13)	0.0045 (12)
C10	0.0457 (19)	0.0491 (18)	0.0451 (17)	−0.0050 (15)	0.0115 (14)	−0.0034 (14)
C11	0.060 (2)	0.054 (2)	0.053 (2)	−0.0171 (18)	0.0127 (17)	−0.0129 (17)
C12	0.070 (3)	0.0332 (17)	0.066 (2)	−0.0128 (16)	0.0264 (19)	−0.0120 (15)
Cu1	0.0392 (2)	0.0291 (2)	0.0397 (2)	0.00421 (14)	0.00535 (15)	0.00074 (14)
N1	0.0554 (17)	0.0373 (14)	0.0479 (16)	0.0027 (12)	−0.0051 (13)	−0.0059 (11)
N2	0.0515 (17)	0.0317 (13)	0.0464 (14)	0.0037 (11)	0.0065 (12)	−0.0001 (11)
N3	0.0537 (18)	0.0477 (16)	0.0474 (15)	0.0124 (14)	0.0022 (13)	0.0019 (13)
N4	0.0568 (18)	0.0386 (14)	0.0483 (16)	0.0009 (13)	0.0148 (13)	0.0022 (12)
N5	0.0394 (14)	0.0306 (12)	0.0390 (13)	0.0036 (10)	0.0061 (10)	0.0011 (10)
N6	0.0409 (14)	0.0326 (12)	0.0412 (13)	−0.0001 (11)	0.0132 (11)	−0.0014 (11)
O1	0.0505 (14)	0.0375 (11)	0.0447 (12)	0.0008 (9)	0.0091 (10)	0.0001 (9)
O2	0.0519 (15)	0.0406 (12)	0.0600 (14)	0.0120 (10)	−0.0020 (11)	−0.0063 (10)
O3	0.095 (2)	0.0483 (14)	0.0791 (19)	0.0180 (14)	−0.0225 (16)	−0.0118 (14)
O4	0.108 (3)	0.077 (2)	0.119 (3)	0.042 (2)	−0.051 (2)	−0.0025 (19)
O5	0.0673 (18)	0.0551 (15)	0.092 (2)	−0.0193 (14)	−0.0152 (15)	0.0131 (14)
O6	0.0885 (19)	0.0425 (13)	0.0500 (13)	−0.0200 (13)	0.0008 (12)	0.0065 (11)
O7	0.0719 (18)	0.0546 (15)	0.0601 (15)	0.0045 (13)	0.0018 (13)	0.0167 (12)

Geometric parameters (Å, º) top

C1—N5	1.322 (4)	C11—C12	1.362 (5)
C1—N1	1.341 (4)	C11—H11	0.9300
C1—C2	1.420 (4)	C12—H12	0.9300
C2—C3	1.356 (5)	Cu1—N5	1.914 (2)
C2—H2	0.9300	Cu1—O2	1.952 (2)
C3—C4	1.412 (5)	Cu1—N6	2.097 (2)
C3—H3	0.9300	Cu1—N2	2.102 (2)
C4—C9	1.387 (4)	Cu1—O1	2.232 (2)
C4—C5	1.437 (5)	N1—N2	1.422 (3)
C5—C6	1.351 (5)	N1—H1	0.8600
C5—H5	0.9300	N2—H2A	0.9000
C6—C7	1.425 (5)	N2—H2B	0.9000
C6—H6	0.9300	N3—O4	1.190 (4)
C7—C12	1.405 (5)	N3—O3	1.213 (4)
C7—C8	1.412 (4)	N3—O2	1.280 (3)
C8—N6	1.363 (4)	N4—O5	1.234 (3)
C8—C9	1.413 (4)	N4—O7	1.239 (3)
C9—N5	1.358 (4)	N4—O6	1.240 (3)
C10—N6	1.332 (4)	O1—H9	0.8422
C10—C11	1.402 (5)	O1—H13	0.8485
C10—H10	0.9300

N5—C1—N1	114.9 (3)	N5—Cu1—O2	168.02 (11)
N5—C1—C2	120.2 (3)	N5—Cu1—N6	80.55 (10)
N1—C1—C2	125.0 (3)	O2—Cu1—N6	94.10 (9)
C3—C2—C1	118.9 (3)	N5—Cu1—N2	77.72 (10)
C3—C2—H2	120.5	O2—Cu1—N2	106.66 (9)
C1—C2—H2	120.5	N6—Cu1—N2	158.07 (10)
C2—C3—C4	121.3 (3)	N5—Cu1—O1	101.19 (9)
C2—C3—H3	119.4	O2—Cu1—O1	89.57 (10)
C4—C3—H3	119.4	N6—Cu1—O1	91.11 (8)
C9—C4—C3	116.6 (3)	N2—Cu1—O1	95.94 (9)
C9—C4—C5	116.6 (3)	C1—N1—N2	116.0 (2)
C3—C4—C5	126.9 (3)	C1—N1—H1	122.0
C6—C5—C4	121.0 (3)	N2—N1—H1	122.0
C6—C5—H5	119.5	N1—N2—Cu1	109.92 (17)
C4—C5—H5	119.5	N1—N2—H2A	109.7
C5—C6—C7	122.5 (3)	Cu1—N2—H2A	109.7
C5—C6—H6	118.8	N1—N2—H2B	109.7
C7—C6—H6	118.8	Cu1—N2—H2B	109.7
C12—C7—C8	115.7 (3)	H2A—N2—H2B	108.2
C12—C7—C6	126.6 (3)	O4—N3—O3	120.0 (3)
C8—C7—C6	117.8 (3)	O4—N3—O2	119.7 (3)
N6—C8—C7	124.3 (3)	O3—N3—O2	120.2 (3)
N6—C8—C9	117.0 (3)	O5—N4—O7	121.6 (3)
C7—C8—C9	118.7 (3)	O5—N4—O6	119.3 (3)
N5—C9—C4	122.0 (3)	O7—N4—O6	119.1 (3)
N5—C9—C8	114.6 (3)	C1—N5—C9	121.1 (3)
C4—C9—C8	123.4 (3)	C1—N5—Cu1	121.3 (2)
N6—C10—C11	121.9 (3)	C9—N5—Cu1	117.6 (2)
N6—C10—H10	119.0	C10—N6—C8	117.6 (3)
C11—C10—H10	119.0	C10—N6—Cu1	132.3 (2)
C12—C11—C10	120.2 (3)	C8—N6—Cu1	109.92 (19)
C12—C11—H11	119.9	Cu1—O1—H9	104.8
C10—C11—H11	119.9	Cu1—O1—H13	106.4
C11—C12—C7	120.2 (3)	H9—O1—H13	108.2
C11—C12—H12	119.9	N3—O2—Cu1	123.3 (2)
C7—C12—H12	119.9

N5—C1—C2—C3	−1.2 (5)	N1—C1—N5—Cu1	−3.2 (4)
N1—C1—C2—C3	179.7 (3)	C2—C1—N5—Cu1	177.6 (2)
C1—C2—C3—C4	0.7 (5)	C4—C9—N5—C1	1.2 (4)
C2—C3—C4—C9	0.7 (5)	C8—C9—N5—C1	−179.4 (3)
C2—C3—C4—C5	−179.4 (3)	C4—C9—N5—Cu1	−176.2 (2)
C9—C4—C5—C6	0.2 (5)	C8—C9—N5—Cu1	3.2 (3)
C3—C4—C5—C6	−179.7 (3)	O2—Cu1—N5—C1	113.5 (5)
C4—C5—C6—C7	0.5 (5)	N6—Cu1—N5—C1	177.7 (2)
C5—C6—C7—C12	179.3 (3)	N2—Cu1—N5—C1	0.7 (2)
C5—C6—C7—C8	−0.5 (5)	O1—Cu1—N5—C1	−93.0 (2)
C12—C7—C8—N6	−0.5 (4)	O2—Cu1—N5—C9	−69.0 (5)
C6—C7—C8—N6	179.3 (3)	N6—Cu1—N5—C9	−4.8 (2)
C12—C7—C8—C9	180.0 (3)	N2—Cu1—N5—C9	178.2 (2)
C6—C7—C8—C9	−0.2 (4)	O1—Cu1—N5—C9	84.5 (2)
C3—C4—C9—N5	−1.7 (4)	C11—C10—N6—C8	1.7 (5)
C5—C4—C9—N5	178.4 (3)	C11—C10—N6—Cu1	−172.6 (2)
C3—C4—C9—C8	179.0 (3)	C7—C8—N6—C10	−0.6 (4)
C5—C4—C9—C8	−0.9 (4)	C9—C8—N6—C10	178.9 (3)
N6—C8—C9—N5	2.0 (4)	C7—C8—N6—Cu1	174.9 (2)
C7—C8—C9—N5	−178.4 (3)	C9—C8—N6—Cu1	−5.5 (3)
N6—C8—C9—C4	−178.6 (3)	N5—Cu1—N6—C10	−179.9 (3)
C7—C8—C9—C4	0.9 (4)	O2—Cu1—N6—C10	−10.7 (3)
N6—C10—C11—C12	−1.8 (5)	N2—Cu1—N6—C10	−172.0 (3)
C10—C11—C12—C7	0.6 (5)	O1—Cu1—N6—C10	79.0 (3)
C8—C7—C12—C11	0.5 (5)	N5—Cu1—N6—C8	5.51 (18)
C6—C7—C12—C11	−179.3 (3)	O2—Cu1—N6—C8	174.71 (19)
N5—C1—N1—N2	4.7 (4)	N2—Cu1—N6—C8	13.3 (4)
C2—C1—N1—N2	−176.2 (3)	O1—Cu1—N6—C8	−95.65 (19)
C1—N1—N2—Cu1	−4.0 (3)	O4—N3—O2—Cu1	179.2 (3)
N5—Cu1—N2—N1	1.71 (19)	O3—N3—O2—Cu1	0.9 (5)
O2—Cu1—N2—N1	−166.8 (2)	N5—Cu1—O2—N3	−105.8 (5)
N6—Cu1—N2—N1	−6.2 (4)	N6—Cu1—O2—N3	−168.8 (3)
O1—Cu1—N2—N1	101.9 (2)	N2—Cu1—O2—N3	4.1 (3)
N1—C1—N5—C9	179.4 (3)	O1—Cu1—O2—N3	100.2 (3)
C2—C1—N5—C9	0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6ⁱ	0.86	2.18	2.936 (4)	146
N1—H1···O7ⁱ	0.86	2.54	3.181 (4)	132
N2—H2A···O3ⁱⁱ	0.90	2.22	3.111 (4)	169
N2—H2B···O7ⁱⁱⁱ	0.90	2.17	3.055 (4)	168
O1—H9···O5ⁱⁱⁱ	0.84	1.98	2.818 (3)	175
O1—H9···O7ⁱⁱⁱ	0.84	2.58	3.185 (3)	130
O1—H13···O6^iv	0.85	1.99	2.821 (3)	167
C2—H2···O6ⁱ	0.93	2.56	3.253 (4)	132
C3—H3···O1^v	0.93	2.48	3.280 (4)	144
C11—H11···O4^vi	0.93	2.43	3.118 (5)	131

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

Experimental details

Crystal data
Chemical formula	[Cu(NO₃)(C₁₂H₁₀N₄)(H₂O)]NO₃
M_r	415.82
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.7175 (8), 10.7746 (10), 16.4725 (16)
β (°)	97.175 (2)
V (Å³)	1535.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.48
Crystal size (mm)	0.50 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.525, 0.843
No. of measured, independent and observed [I > 2σ(I)] reflections	8857, 3329, 2735
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.112, 1.03
No. of reflections	3329
No. of parameters	235
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.33

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6ⁱ	0.86	2.18	2.936 (4)	145.9
N1—H1···O7ⁱ	0.86	2.54	3.181 (4)	132.1
N2—H2A···O3ⁱⁱ	0.90	2.22	3.111 (4)	169.4
N2—H2B···O7ⁱⁱⁱ	0.90	2.17	3.055 (4)	168.2
O1—H9···O5ⁱⁱⁱ	0.84	1.98	2.818 (3)	174.7
O1—H9···O7ⁱⁱⁱ	0.84	2.58	3.185 (3)	130.2
O1—H13···O6^iv	0.85	1.99	2.821 (3)	166.8
C2—H2···O6ⁱ	0.93	2.56	3.253 (4)	132.1
C3—H3···O1^v	0.93	2.48	3.280 (4)	143.7
C11—H11···O4^vi	0.93	2.43	3.118 (5)	131.1

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

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lewis, J. & O'Donoghue, T. D. (1980). J. Chem. Soc. Dalton Trans. pp. 736–742. CrossRef Web of Science Google Scholar
Liu, Q. S., Liu, L. D. & Shi, J. M. (2008). Acta Cryst. C64, m58–m60. 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page m847

doi:10.1107/S1600536808015523

Open

access