Bis(cyanamide-κN)[4-(1H-imidazol-1-yl)phenol-κN]bis-(nitrato-κO)copper(II).

A pair of linear cyanamide (NCNH(2)) ligands, two monodentate 4-(1H-imidazol-1-yl)phenol (L) ligands and two nitrate anions link the Cu(II) atom into a mononuclear unit, [Cu(NO(3))(2)(C(9)H(8)N(2)O)(2)(NCNH(2))(2)]. The coordination polyhedron of the Cu atom is an elongated octa-hedron distorted by Jahn-Teller effects. Inter-molecular O-H⋯O, O-H⋯N, N-H⋯O and N-H⋯N hydrogen-bonding inter-actions link these units into a three-dimensional supra-molecular architecture.

Related literature

For background to related compounds, see: Ferlay et al. (1995 ▶); Ribas et al. (1999 ▶). For related structures, see: Becker et al. (2000 ▶); Berger & Schnick (1994 ▶); Liao & Dronskowski (2006 ▶); Liu et al. (2005 ▶); Meyer et al. (2000 ▶); Chaudhuri et al. (1985 ▶); Tanabe et al. (2002 ▶); Yuan et al. (2004 ▶, 2007 ▶).

Experimental

Crystal data

[Cu(NO3)2(C9H8N2O)2(CH2N2)2]

M = 592.00

Triclinic,

a = 8.2235 (7) Å

b = 8.7144 (8) Å

c = 9.4553 (9) Å

α = 110.808 (1)°

β = 96.696 (2)°

γ = 98.883 (2)°

V = 614.92 (10) Å3

Z = 1

Mo Kα radiation

μ = 0.96 mm−1

T = 273 K

0.25 × 0.21 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.796, T max = 0.847

4951 measured reflections

2396 independent reflections

2229 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.105

S = 1.07

2396 reflections

178 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811032399/pk2338sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032399/pk2338Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(NO3)2(C9H8N2O)2(CH2N2)2]	Z = 1
Mr = 592.00	F(000) = 303
Triclinic, P1	Dx = 1.599 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2235 (7) Å	Cell parameters from 2396 reflections
b = 8.7144 (8) Å	θ = 2.4–26.0°
c = 9.4553 (9) Å	µ = 0.96 mm−1
α = 110.808 (1)°	T = 273 K
β = 96.696 (2)°	Block, blue
γ = 98.883 (2)°	0.25 × 0.21 × 0.18 mm
V = 614.92 (10) Å3

Bruker SMART CCD area-detector diffractometer	2396 independent reflections
Radiation source: fine-focus sealed tube	2229 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −9→10
Tmin = 0.796, Tmax = 0.847	k = −10→10
4951 measured reflections	l = −11→11

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.059P)2 + 0.2239P] where P = (Fo2 + 2Fc2)/3
2396 reflections	(Δ/σ)max < 0.001
178 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cu1	0.0000	0.5000	0.0000	0.03730 (17)
O1	1.0200 (2)	1.3124 (2)	0.3638 (2)	0.0522 (5)
HO1	1.0559	1.3039	0.2822	0.078*
O3	0.1612 (2)	0.3321 (3)	0.1247 (2)	0.0588 (5)
O4	0.3655 (3)	0.4115 (4)	0.3168 (3)	0.0738 (7)
O2	0.4149 (3)	0.4075 (3)	0.0983 (2)	0.0598 (5)
N1	−0.1364 (3)	0.5376 (3)	0.1629 (3)	0.0465 (5)
N2	−0.2913 (3)	0.5888 (3)	0.3748 (3)	0.0516 (6)
HN2B	−0.3876	0.5230	0.3578	0.062*
HN2A	−0.2331	0.6083	0.4636	0.062*
N3	0.1547 (3)	0.7184 (2)	0.1239 (2)	0.0390 (5)
N4	0.3757 (2)	0.9254 (2)	0.2240 (2)	0.0389 (5)
N5	0.3155 (3)	0.3834 (3)	0.1788 (3)	0.0433 (5)
C1	0.1064 (3)	0.8598 (3)	0.2122 (3)	0.0473 (6)
H1	−0.0025	0.8663	0.2274	0.057*
C2	0.2407 (3)	0.9884 (3)	0.2740 (3)	0.0484 (7)
H2	0.2417	1.0981	0.3378	0.058*
C3	0.3189 (3)	0.7628 (3)	0.1334 (3)	0.0392 (6)
H3	0.3853	0.6910	0.0841	0.047*
C4	0.5449 (3)	1.0196 (3)	0.2591 (3)	0.0372 (5)
C5	0.6081 (3)	1.1383 (3)	0.4066 (3)	0.0459 (6)
H5	0.5432	1.1533	0.4828	0.055*
C6	0.7685 (3)	1.2339 (3)	0.4393 (3)	0.0460 (6)
H6	0.8122	1.3130	0.5381	0.055*
C7	0.8639 (3)	1.2124 (3)	0.3258 (3)	0.0393 (6)
C8	0.8007 (3)	1.0926 (3)	0.1790 (3)	0.0427 (6)
H8	0.8656	1.0774	0.1028	0.051*
C9	0.6406 (3)	0.9957 (3)	0.1462 (3)	0.0415 (6)
H9	0.5980	0.9146	0.0481	0.050*
C10	−0.2100 (3)	0.5568 (3)	0.2602 (3)	0.0387 (6)

	U11	U22	U33	U12	U13	U23
Cu1	0.0265 (2)	0.0408 (3)	0.0357 (3)	−0.00682 (16)	0.00593 (17)	0.00971 (18)
O1	0.0305 (10)	0.0649 (12)	0.0477 (11)	−0.0127 (8)	0.0005 (8)	0.0169 (9)
O3	0.0357 (11)	0.0773 (14)	0.0555 (12)	−0.0089 (9)	0.0010 (9)	0.0269 (10)
O4	0.0382 (12)	0.125 (2)	0.0533 (13)	−0.0089 (12)	0.0036 (10)	0.0399 (13)
O2	0.0486 (12)	0.0711 (13)	0.0574 (13)	0.0021 (10)	0.0240 (10)	0.0215 (10)
N1	0.0330 (12)	0.0554 (13)	0.0397 (12)	−0.0069 (10)	0.0084 (10)	0.0108 (10)
N2	0.0368 (12)	0.0724 (15)	0.0368 (12)	0.0016 (11)	0.0091 (10)	0.0138 (11)
N3	0.0290 (11)	0.0387 (11)	0.0431 (12)	−0.0023 (8)	0.0051 (9)	0.0127 (9)
N4	0.0281 (11)	0.0352 (10)	0.0461 (12)	−0.0018 (8)	0.0040 (9)	0.0111 (9)
N5	0.0352 (12)	0.0428 (11)	0.0474 (13)	0.0025 (9)	0.0101 (10)	0.0132 (10)
C1	0.0298 (13)	0.0472 (14)	0.0621 (17)	0.0050 (11)	0.0115 (12)	0.0176 (13)
C2	0.0367 (14)	0.0362 (13)	0.0633 (18)	0.0045 (10)	0.0115 (13)	0.0090 (12)
C3	0.0291 (12)	0.0369 (12)	0.0439 (14)	−0.0008 (10)	0.0059 (10)	0.0098 (10)
C4	0.0279 (12)	0.0341 (11)	0.0448 (14)	−0.0013 (9)	0.0027 (10)	0.0139 (10)
C5	0.0369 (14)	0.0490 (14)	0.0430 (14)	−0.0049 (11)	0.0085 (11)	0.0125 (11)
C6	0.0392 (14)	0.0472 (14)	0.0378 (14)	−0.0070 (11)	0.0001 (11)	0.0086 (11)
C7	0.0279 (12)	0.0402 (12)	0.0461 (14)	−0.0017 (10)	0.0002 (10)	0.0175 (11)
C8	0.0338 (13)	0.0488 (14)	0.0415 (14)	0.0039 (11)	0.0086 (11)	0.0139 (11)
C9	0.0342 (13)	0.0382 (12)	0.0405 (14)	−0.0001 (10)	−0.0006 (11)	0.0069 (10)
C10	0.0281 (12)	0.0408 (13)	0.0386 (14)	−0.0028 (10)	−0.0008 (11)	0.0114 (10)

Cu1—N1	1.974 (2)	N4—C2	1.372 (3)
Cu1—N1i	1.974 (2)	N4—C4	1.438 (3)
Cu1—N3	1.9837 (19)	C1—C2	1.349 (4)
Cu1—N3i	1.9837 (19)	C1—H1	0.9300
O1—C7	1.365 (3)	C2—H2	0.9300
O1—HO1	0.8409	C3—H3	0.9300
O3—N5	1.259 (3)	C4—C9	1.375 (4)
O4—N5	1.244 (3)	C4—C5	1.388 (4)
O2—N5	1.224 (3)	C5—C6	1.383 (4)
N1—C10	1.136 (3)	C5—H5	0.9300
N2—C10	1.308 (3)	C6—C7	1.378 (4)
N2—HN2B	0.8638	C6—H6	0.9300
N2—HN2A	0.8613	C7—C8	1.386 (4)
N3—C3	1.329 (3)	C8—C9	1.385 (3)
N3—C1	1.368 (3)	C8—H8	0.9300
N4—C3	1.342 (3)	C9—H9	0.9300
N1—Cu1—N1i	180.00 (14)	C1—C2—H2	126.8
N1—Cu1—N3	89.82 (9)	N4—C2—H2	126.8
N1i—Cu1—N3	90.18 (8)	N3—C3—N4	110.7 (2)
N1—Cu1—N3i	90.18 (9)	N3—C3—H3	124.7
N1i—Cu1—N3i	89.82 (8)	N4—C3—H3	124.7
N3—Cu1—N3i	180.0	C9—C4—C5	120.6 (2)
C7—O1—HO1	108.5	C9—C4—N4	120.2 (2)
C10—N1—Cu1	177.0 (2)	C5—C4—N4	119.1 (2)
C10—N2—HN2B	116.0	C6—C5—C4	119.4 (3)
C10—N2—HN2A	115.8	C6—C5—H5	120.3
HN2B—N2—HN2A	112.2	C4—C5—H5	120.3
C3—N3—C1	106.0 (2)	C7—C6—C5	120.2 (2)
C3—N3—Cu1	129.22 (18)	C7—C6—H6	119.9
C1—N3—Cu1	124.71 (17)	C5—C6—H6	119.9
C3—N4—C2	107.3 (2)	O1—C7—C6	117.7 (2)
C3—N4—C4	127.0 (2)	O1—C7—C8	122.1 (2)
C2—N4—C4	125.7 (2)	C6—C7—C8	120.2 (2)
O2—N5—O4	120.4 (2)	C9—C8—C7	119.7 (2)
O2—N5—O3	120.9 (2)	C9—C8—H8	120.1
O4—N5—O3	118.8 (2)	C7—C8—H8	120.1
C2—C1—N3	109.6 (2)	C4—C9—C8	119.8 (2)
C2—C1—H1	125.2	C4—C9—H9	120.1
N3—C1—H1	125.2	C8—C9—H9	120.1
C1—C2—N4	106.5 (2)	N1—C10—N2	176.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—HO1···O3ii	0.84	1.88	2.704 (3)	168.
O1—HO1···O4ii	0.84	2.51	2.970 (3)	115.
O1—HO1···N5ii	0.84	2.55	3.262 (3)	143.
N2—HN2B···O4iii	0.86	2.04	2.888 (3)	168.
N2—HN2B···O2iii	0.86	2.55	3.096 (3)	122.
N2—HN2B···N5iii	0.86	2.64	3.399 (3)	148.
N2—HN2A···O1iv	0.86	2.09	2.904 (3)	157.
N2—HN2A···O4v	0.86	2.50	3.049 (3)	122.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—HO1⋯O3i	0.84	1.88	2.704 (3)	168
O1—HO1⋯O4i	0.84	2.51	2.970 (3)	115
O1—HO1⋯N5i	0.84	2.55	3.262 (3)	143
N2—HN2B⋯O4ii	0.86	2.04	2.888 (3)	168
N2—HN2B⋯O2ii	0.86	2.55	3.096 (3)	122
N2—HN2B⋯N5ii	0.86	2.64	3.399 (3)	148
N2—HN2A⋯O1iii	0.86	2.09	2.904 (3)	157
N2—HN2A⋯O4iv	0.86	2.50	3.049 (3)	122

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .