Bis(nitrato-κO)tetra­kis­[1-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-1-one]copper(II)

Cai, H.; Guo, Y.; Li, J.-G.; Wu, Y.

doi:10.1107/S160053681103529X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page m1385

https://doi.org/10.1107/S160053681103529X

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Bis(nitrato-κO)tetrakis[1-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-1-one]copper(II)

Hua Cai,^a ^* Ying Guo,^a Jian-Gang Li ^a and Yao Wu ^a

^aCollege of Science, Civil Aviation University of China, Tianjin 300300, People's Republic of China
^*Correspondence e-mail: caihua-1109@163.com

(Received 17 August 2011; accepted 29 August 2011; online 14 September 2011)

In the title complex, [Cu(NO₃)₂(C₁₁H₁₁N₃O)₄], the Cu^II atom is situated on a centre of inversion and is coordinated by two O atoms from two nitrate anions and four N atoms from four monodentate 1-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-1-one ligands in a distorted octahedral geometry. Weak intermolecular C—H⋯O and C—H⋯N hydrogen bonds result in a supramolecular layer parallel to (101). These layers are connected by π–π interactions between the benzene rings [centroid–centroid distance = 3.891 (2) Å].

Related literature

For background to complexes with neutral N-containing ligands, see: Barnett & Champness (2003 ); Roesky & Andruh (2003 ); Zaworotko (2001 ). For a related structure, see: Cai et al. (2010 ).

Experimental

Crystal data

[Cu(NO₃)₂(C₁₁H₁₁N₃O)₄]
M_r = 992.47
Triclinic, $[P \overline 1]$
a = 7.7742 (14) Å
b = 12.472 (2) Å
c = 12.498 (2) Å
α = 102.232 (3)°
β = 100.737 (3)°
γ = 104.394 (3)°
V = 1110.0 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.57 mm⁻¹
T = 296 K
0.24 × 0.20 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.876, T_max = 0.925
5737 measured reflections
3905 independent reflections
3295 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.105
S = 1.03
3905 reflections
313 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯N2ⁱ	0.97	2.50	3.368 (4)	148
C19—H19⋯O5ⁱⁱ	0.93	2.56	3.291 (4)	136
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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) and DIAMOND (Brandenburg & Berndt, 1999 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681103529X/hy2463sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681103529X/hy2463Isup2.hkl

checkCIF report

Comment top

Neutral organic ligands containing rigid or flexible spacers, such as 4,4'-bipyridine, 1,2-bis(4-pyridyl)ethane, 1,2-bis(4-pyridyl)propane and many others, have been used to generate a rich variety of metal-organic architectures with different metal ions by various reaction procedures (Barnett & Champness, 2003; Roesky & Andruh, 2003; Zaworotko, 2001). Recently, we have initiated a research program of synthesizing supermolecules based on pseudohalides and a flexible ligand, which consists of a propanone unit substituted with a triazole and a phenyl group (Cai et al., 2010). To further explore this series, we synthesized the title compound, a new Cu(II) complex based on the ligand 1-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-1-one (L).

In the neutral mononuclear title complex (Fig. 1), the Cu^II atom is six-coordinated by four monodentate L ligands in the equatorial plane and two O atoms from two NO₃^- anions in the axial positions, displaying a CuN₄O₂ octahedral geometry. The triazol and phenyl rings in the ligands are not coplanar. The dihedral angels formed by the least-squares planes of the phenyl and triazole rings are 43.8 (2) and 65.9 (2)°. Weak intermolecular C—H···O and C—H···N hydrogen bonds (Table 1) extend the monomeric units into a two-dimensional supramolecular layer parallel to (1 0 1), as shown in Fig. 2.

Related literature top

For background to complexes with neutral N-containing ligands, see: Barnett & Champness (2003); Roesky & Andruh (2003); Zaworotko (2001). For a related structure, see: Cai et al. (2010).

Experimental top

Cu(NO₃)₂.3H₂O (24.2 mg, 0.1 mmol) and L (22.3 mg, 0.1 mmol) were mixed in a CH₃CN/H₂O (20 ml, v/v 1:1) solution with vigorous stirring for ca 30 min. The resulting solution was filtered and left to stand at room temperature. Colourless block crystals of the title compound suitable for X-ray analysis were obtained in 65% yield by slow evaporation of the solvent over a period of 1 week. Analysis, calculated for C₄₆H₄₄MnN₁₄O₄S₂: C 53.25, H 4.47, N 19.76%; found: C 53.45, H 4.43, N 19.62%.

Structure description top

For background to complexes with neutral N-containing ligands, see: Barnett & Champness (2003); Roesky & Andruh (2003); Zaworotko (2001). For a related structure, see: Cai et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (A) -x, 1-y, -z.]
	Fig. 2. The two-dimensional layer structure of the title compound, showing C—H···O and C—H···N hydrogen bonds as red dashed lines.

Bis(nitrato-κO)tetrakis[1-phenyl-3-(1H-1,2,4-triazol- 1-yl)propan-1-one]copper(II) top

Crystal data top

[Cu(NO₃)₂(C₁₁H₁₁N₃O)₄]	Z = 1
M_r = 992.47	F(000) = 515
Triclinic, P1	D_x = 1.485 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7742 (14) Å	Cell parameters from 2167 reflections
b = 12.472 (2) Å	θ = 2.8–25.5°
c = 12.498 (2) Å	µ = 0.57 mm⁻¹
α = 102.232 (3)°	T = 296 K
β = 100.737 (3)°	Block, blue
γ = 104.394 (3)°	0.24 × 0.20 × 0.14 mm
V = 1110.0 (3) Å³

Data collection top

Bruker APEXII CCD diffractometer	3905 independent reflections
Radiation source: fine-focus sealed tube	3295 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.876, T_max = 0.925	k = −14→10
5737 measured reflections	l = −13→14

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0485P)² + 0.6085P] where P = (F_o² + 2F_c²)/3
3905 reflections	(Δ/σ)_max < 0.001
313 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Cu(NO₃)₂(C₁₁H₁₁N₃O)₄]	γ = 104.394 (3)°
M_r = 992.47	V = 1110.0 (3) Å³
Triclinic, P1	Z = 1
a = 7.7742 (14) Å	Mo Kα radiation
b = 12.472 (2) Å	µ = 0.57 mm⁻¹
c = 12.498 (2) Å	T = 296 K
α = 102.232 (3)°	0.24 × 0.20 × 0.14 mm
β = 100.737 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3905 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3295 reflections with I > 2σ(I)
T_min = 0.876, T_max = 0.925	R_int = 0.016
5737 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.03	Δρ_max = 0.55 e Å⁻³
3905 reflections	Δρ_min = −0.34 e Å⁻³
313 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.0000	0.5000	0.0000	0.03192 (15)
O1	0.1209 (3)	−0.14388 (17)	−0.15924 (18)	0.0600 (6)
O2	0.6023 (4)	0.8407 (2)	0.42668 (19)	0.0725 (7)
O3	−0.2044 (3)	0.38551 (18)	0.0827 (2)	0.0617 (6)
O4	−0.4197 (4)	0.2377 (2)	−0.0202 (2)	0.0874 (8)
O5	−0.4769 (4)	0.3628 (3)	0.1018 (3)	0.1086 (11)
N1	0.0657 (3)	0.36119 (17)	−0.06904 (17)	0.0338 (5)
N2	0.2167 (4)	0.26287 (19)	−0.1668 (2)	0.0493 (6)
N3	0.1188 (3)	0.19722 (17)	−0.11162 (17)	0.0351 (5)
N4	0.1884 (3)	0.51953 (16)	0.14694 (16)	0.0335 (5)
N5	0.3189 (3)	0.47333 (18)	0.29969 (18)	0.0414 (5)
N6	0.4316 (3)	0.56936 (17)	0.28594 (17)	0.0330 (5)
N7	−0.3682 (3)	0.3303 (2)	0.0570 (2)	0.0495 (6)
C1	0.0307 (4)	0.2570 (2)	−0.0540 (2)	0.0374 (6)
H1	−0.0444	0.2297	−0.0097	0.045*
C2	0.1795 (4)	0.3605 (2)	−0.1381 (2)	0.0468 (7)
H2	0.2276	0.4237	−0.1633	0.056*
C3	0.1336 (4)	0.0823 (2)	−0.1151 (2)	0.0426 (6)
H3A	0.0389	0.0418	−0.0848	0.051*
H3B	0.2518	0.0884	−0.0681	0.051*
C4	0.1139 (4)	0.0150 (2)	−0.2340 (2)	0.0397 (6)
H4A	0.2116	0.0543	−0.2630	0.048*
H4B	−0.0020	0.0122	−0.2815	0.048*
C5	0.1208 (3)	−0.1061 (2)	−0.2409 (2)	0.0382 (6)
C6	0.1233 (3)	−0.1786 (2)	−0.3521 (2)	0.0376 (6)
C7	0.0983 (4)	−0.1428 (2)	−0.4503 (2)	0.0486 (7)
H7	0.0843	−0.0704	−0.4472	0.058*
C8	0.0941 (4)	−0.2141 (3)	−0.5531 (3)	0.0581 (8)
H8	0.0746	−0.1901	−0.6187	0.070*
C9	0.1190 (4)	−0.3198 (3)	−0.5576 (3)	0.0610 (9)
H9	0.1160	−0.3677	−0.6264	0.073*
C10	0.1481 (4)	−0.3550 (2)	−0.4609 (3)	0.0581 (9)
H10	0.1668	−0.4264	−0.4644	0.070*
C11	0.1500 (4)	−0.2856 (2)	−0.3582 (3)	0.0461 (7)
H11	0.1692	−0.3105	−0.2932	0.055*
C12	0.3529 (3)	0.5953 (2)	0.1955 (2)	0.0332 (6)
H12	0.4050	0.6574	0.1698	0.040*
C13	0.1750 (4)	0.4467 (2)	0.2141 (2)	0.0412 (6)
H13	0.0727	0.3835	0.2006	0.049*
C14	0.6175 (3)	0.6206 (2)	0.3603 (2)	0.0400 (6)
H14A	0.6857	0.6797	0.3316	0.048*
H14B	0.6794	0.5618	0.3585	0.048*
C15	0.6195 (4)	0.6732 (2)	0.4821 (2)	0.0383 (6)
H15A	0.5158	0.6264	0.5009	0.046*
H15B	0.7306	0.6721	0.5317	0.046*
C16	0.6107 (4)	0.7953 (2)	0.5032 (2)	0.0409 (6)
C17	0.6149 (3)	0.8587 (2)	0.6201 (2)	0.0382 (6)
C18	0.6220 (4)	0.8080 (2)	0.7086 (2)	0.0445 (7)
H18	0.6255	0.7325	0.6964	0.053*
C19	0.6238 (4)	0.8694 (3)	0.8155 (3)	0.0580 (8)
H19	0.6280	0.8348	0.8745	0.070*
C20	0.6193 (4)	0.9811 (3)	0.8344 (3)	0.0600 (9)
H20	0.6210	1.0220	0.9062	0.072*
C21	0.6123 (4)	1.0324 (3)	0.7475 (3)	0.0601 (9)
H21	0.6091	1.1081	0.7605	0.072*
C22	0.6099 (4)	0.9717 (2)	0.6406 (3)	0.0504 (7)
H22	0.6049	1.0069	0.5819	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0358 (3)	0.0315 (2)	0.0255 (2)	0.01221 (18)	0.00439 (18)	0.00191 (17)
O1	0.0937 (17)	0.0467 (12)	0.0502 (13)	0.0292 (12)	0.0234 (12)	0.0209 (10)
O2	0.126 (2)	0.0701 (15)	0.0463 (13)	0.0520 (15)	0.0302 (14)	0.0325 (12)
O3	0.0424 (12)	0.0555 (13)	0.0895 (17)	0.0057 (10)	0.0197 (11)	0.0325 (12)
O4	0.095 (2)	0.0634 (16)	0.0724 (18)	−0.0020 (14)	−0.0014 (15)	0.0032 (14)
O5	0.102 (2)	0.094 (2)	0.170 (3)	0.0450 (18)	0.096 (2)	0.048 (2)
N1	0.0401 (12)	0.0319 (11)	0.0282 (11)	0.0125 (9)	0.0091 (9)	0.0031 (9)
N2	0.0711 (17)	0.0410 (13)	0.0495 (15)	0.0233 (12)	0.0348 (13)	0.0159 (11)
N3	0.0445 (12)	0.0296 (11)	0.0316 (11)	0.0116 (9)	0.0123 (10)	0.0063 (9)
N4	0.0382 (12)	0.0321 (11)	0.0281 (11)	0.0103 (9)	0.0050 (9)	0.0070 (9)
N5	0.0489 (13)	0.0389 (12)	0.0352 (13)	0.0097 (10)	0.0065 (11)	0.0155 (10)
N6	0.0361 (11)	0.0338 (11)	0.0277 (11)	0.0090 (9)	0.0071 (9)	0.0079 (9)
N7	0.0480 (15)	0.0492 (15)	0.0577 (16)	0.0122 (12)	0.0174 (13)	0.0272 (13)
C1	0.0429 (15)	0.0340 (14)	0.0332 (14)	0.0084 (11)	0.0137 (12)	0.0050 (11)
C2	0.069 (2)	0.0383 (15)	0.0432 (16)	0.0201 (14)	0.0271 (15)	0.0153 (12)
C3	0.0554 (17)	0.0328 (14)	0.0414 (16)	0.0169 (12)	0.0116 (13)	0.0100 (12)
C4	0.0471 (15)	0.0319 (13)	0.0381 (15)	0.0149 (12)	0.0068 (12)	0.0054 (11)
C5	0.0360 (14)	0.0334 (13)	0.0428 (16)	0.0097 (11)	0.0065 (12)	0.0096 (12)
C6	0.0321 (13)	0.0309 (13)	0.0446 (16)	0.0066 (10)	0.0067 (12)	0.0055 (11)
C7	0.0565 (18)	0.0384 (15)	0.0459 (17)	0.0142 (13)	0.0092 (14)	0.0044 (13)
C8	0.061 (2)	0.0571 (19)	0.0442 (18)	0.0099 (16)	0.0091 (15)	0.0020 (15)
C9	0.0533 (19)	0.0520 (19)	0.061 (2)	0.0097 (15)	0.0167 (16)	−0.0149 (16)
C10	0.0476 (17)	0.0343 (15)	0.086 (3)	0.0137 (13)	0.0185 (17)	−0.0007 (16)
C11	0.0393 (15)	0.0345 (14)	0.064 (2)	0.0112 (12)	0.0145 (14)	0.0115 (13)
C12	0.0392 (14)	0.0333 (13)	0.0278 (13)	0.0104 (11)	0.0094 (11)	0.0097 (10)
C13	0.0470 (16)	0.0364 (14)	0.0347 (15)	0.0060 (12)	0.0066 (12)	0.0090 (11)
C14	0.0334 (14)	0.0492 (16)	0.0356 (15)	0.0142 (12)	0.0054 (11)	0.0087 (12)
C15	0.0376 (14)	0.0430 (15)	0.0302 (14)	0.0095 (12)	0.0012 (11)	0.0110 (11)
C16	0.0413 (15)	0.0482 (16)	0.0348 (15)	0.0152 (12)	0.0050 (12)	0.0166 (12)
C17	0.0333 (13)	0.0407 (14)	0.0349 (15)	0.0078 (11)	0.0016 (11)	0.0089 (11)
C18	0.0502 (16)	0.0390 (15)	0.0350 (15)	0.0042 (12)	0.0039 (12)	0.0076 (12)
C19	0.066 (2)	0.0575 (19)	0.0357 (17)	0.0012 (16)	0.0055 (15)	0.0091 (14)
C20	0.057 (2)	0.066 (2)	0.0393 (18)	0.0092 (16)	0.0051 (15)	−0.0056 (15)
C21	0.060 (2)	0.0468 (17)	0.061 (2)	0.0198 (15)	−0.0002 (16)	−0.0022 (15)
C22	0.0531 (18)	0.0471 (17)	0.0475 (18)	0.0177 (14)	−0.0001 (14)	0.0138 (14)

Geometric parameters (Å, º) top

Cu1—N1	1.9931 (19)	C6—C11	1.389 (4)
Cu1—N4	2.0515 (19)	C7—C8	1.388 (4)
Cu1—O3	2.396 (2)	C7—H7	0.9300
O1—C5	1.211 (3)	C8—C9	1.370 (4)
O2—C16	1.210 (3)	C8—H8	0.9300
O3—N7	1.232 (3)	C9—C10	1.370 (5)
O4—N7	1.257 (3)	C9—H9	0.9300
O5—N7	1.201 (3)	C10—C11	1.384 (4)
N1—C1	1.321 (3)	C10—H10	0.9300
N1—C2	1.346 (3)	C11—H11	0.9300
N2—C2	1.313 (3)	C12—H12	0.9300
N2—N3	1.360 (3)	C13—H13	0.9300
N3—C1	1.325 (3)	C14—C15	1.520 (4)
N3—C3	1.459 (3)	C14—H14A	0.9700
N4—C12	1.328 (3)	C14—H14B	0.9700
N4—C13	1.360 (3)	C15—C16	1.512 (4)
N5—C13	1.313 (3)	C15—H15A	0.9700
N5—N6	1.361 (3)	C15—H15B	0.9700
N6—C12	1.324 (3)	C16—C17	1.496 (4)
N6—C14	1.467 (3)	C17—C18	1.385 (4)
C1—H1	0.9300	C17—C22	1.391 (4)
C2—H2	0.9300	C18—C19	1.387 (4)
C3—C4	1.503 (4)	C18—H18	0.9300
C3—H3A	0.9700	C19—C20	1.373 (5)
C3—H3B	0.9700	C19—H19	0.9300
C4—C5	1.510 (3)	C20—C21	1.371 (5)
C4—H4A	0.9700	C20—H20	0.9300
C4—H4B	0.9700	C21—C22	1.384 (4)
C5—C6	1.495 (4)	C21—H21	0.9300
C6—C7	1.389 (4)	C22—H22	0.9300

N1—Cu1—N1ⁱ	180.00 (11)	C11—C6—C5	119.3 (3)
N1—Cu1—N4ⁱ	91.68 (8)	C8—C7—C6	120.7 (3)
N1ⁱ—Cu1—N4ⁱ	88.32 (8)	C8—C7—H7	119.7
N1—Cu1—N4	88.32 (8)	C6—C7—H7	119.7
N1ⁱ—Cu1—N4	91.68 (8)	C9—C8—C7	119.8 (3)
N4ⁱ—Cu1—N4	180.00 (11)	C9—C8—H8	120.1
N1—Cu1—O3ⁱ	90.37 (8)	C7—C8—H8	120.1
N1ⁱ—Cu1—O3ⁱ	89.63 (8)	C10—C9—C8	120.1 (3)
N4ⁱ—Cu1—O3ⁱ	82.97 (8)	C10—C9—H9	119.9
N4—Cu1—O3ⁱ	97.03 (8)	C8—C9—H9	119.9
N1—Cu1—O3	89.63 (8)	C9—C10—C11	120.6 (3)
N1ⁱ—Cu1—O3	90.37 (8)	C9—C10—H10	119.7
N4ⁱ—Cu1—O3	97.03 (8)	C11—C10—H10	119.7
N4—Cu1—O3	82.97 (8)	C10—C11—C6	120.1 (3)
O3ⁱ—Cu1—O3	180.0	C10—C11—H11	120.0
N7—O3—Cu1	136.91 (19)	C6—C11—H11	120.0
C1—N1—C2	103.6 (2)	N6—C12—N4	109.9 (2)
C1—N1—Cu1	132.14 (18)	N6—C12—H12	125.1
C2—N1—Cu1	123.99 (17)	N4—C12—H12	125.1
C2—N2—N3	102.5 (2)	N5—C13—N4	114.2 (2)
C1—N3—N2	110.0 (2)	N5—C13—H13	122.9
C1—N3—C3	129.9 (2)	N4—C13—H13	122.9
N2—N3—C3	119.9 (2)	N6—C14—C15	113.0 (2)
C12—N4—C13	103.1 (2)	N6—C14—H14A	109.0
C12—N4—Cu1	131.17 (17)	C15—C14—H14A	109.0
C13—N4—Cu1	125.54 (17)	N6—C14—H14B	109.0
C13—N5—N6	102.6 (2)	C15—C14—H14B	109.0
C12—N6—N5	110.2 (2)	H14A—C14—H14B	107.8
C12—N6—C14	130.0 (2)	C16—C15—C14	113.0 (2)
N5—N6—C14	119.5 (2)	C16—C15—H15A	109.0
O5—N7—O3	122.4 (3)	C14—C15—H15A	109.0
O5—N7—O4	120.4 (3)	C16—C15—H15B	109.0
O3—N7—O4	117.3 (3)	C14—C15—H15B	109.0
N1—C1—N3	109.7 (2)	H15A—C15—H15B	107.8
N1—C1—H1	125.2	O2—C16—C17	121.1 (3)
N3—C1—H1	125.2	O2—C16—C15	120.1 (3)
N2—C2—N1	114.3 (2)	C17—C16—C15	118.8 (2)
N2—C2—H2	122.8	C18—C17—C22	118.7 (3)
N1—C2—H2	122.8	C18—C17—C16	122.1 (2)
N3—C3—C4	111.1 (2)	C22—C17—C16	119.1 (2)
N3—C3—H3A	109.4	C17—C18—C19	120.3 (3)
C4—C3—H3A	109.4	C17—C18—H18	119.8
N3—C3—H3B	109.4	C19—C18—H18	119.8
C4—C3—H3B	109.4	C20—C19—C18	120.2 (3)
H3A—C3—H3B	108.0	C20—C19—H19	119.9
C3—C4—C5	112.3 (2)	C18—C19—H19	119.9
C3—C4—H4A	109.1	C21—C20—C19	120.1 (3)
C5—C4—H4A	109.1	C21—C20—H20	119.9
C3—C4—H4B	109.1	C19—C20—H20	119.9
C5—C4—H4B	109.1	C20—C21—C22	120.0 (3)
H4A—C4—H4B	107.9	C20—C21—H21	120.0
O1—C5—C6	121.2 (2)	C22—C21—H21	120.0
O1—C5—C4	120.9 (2)	C21—C22—C17	120.6 (3)
C6—C5—C4	118.0 (2)	C21—C22—H22	119.7
C7—C6—C11	118.6 (3)	C17—C22—H22	119.7
C7—C6—C5	122.1 (2)

N1—Cu1—O3—N7	−92.4 (3)	C3—C4—C5—C6	−173.5 (2)
N1ⁱ—Cu1—O3—N7	87.6 (3)	O1—C5—C6—C7	171.1 (3)
N4ⁱ—Cu1—O3—N7	−0.8 (3)	C4—C5—C6—C7	−7.5 (4)
N4—Cu1—O3—N7	179.2 (3)	O1—C5—C6—C11	−8.4 (4)
N4ⁱ—Cu1—N1—C1	−107.5 (2)	C4—C5—C6—C11	172.9 (2)
N4—Cu1—N1—C1	72.5 (2)	C11—C6—C7—C8	2.1 (4)
O3ⁱ—Cu1—N1—C1	169.5 (2)	C5—C6—C7—C8	−177.5 (3)
O3—Cu1—N1—C1	−10.5 (2)	C6—C7—C8—C9	−1.5 (5)
N4ⁱ—Cu1—N1—C2	79.8 (2)	C7—C8—C9—C10	−0.1 (5)
N4—Cu1—N1—C2	−100.2 (2)	C8—C9—C10—C11	1.0 (5)
O3ⁱ—Cu1—N1—C2	−3.2 (2)	C9—C10—C11—C6	−0.4 (4)
O3—Cu1—N1—C2	176.8 (2)	C7—C6—C11—C10	−1.2 (4)
C2—N2—N3—C1	−0.2 (3)	C5—C6—C11—C10	178.4 (2)
C2—N2—N3—C3	−175.6 (2)	N5—N6—C12—N4	0.2 (3)
N1—Cu1—N4—C12	107.1 (2)	C14—N6—C12—N4	173.7 (2)
N1ⁱ—Cu1—N4—C12	−72.9 (2)	C13—N4—C12—N6	−0.2 (3)
O3ⁱ—Cu1—N4—C12	16.9 (2)	Cu1—N4—C12—N6	−175.26 (16)
O3—Cu1—N4—C12	−163.1 (2)	N6—N5—C13—N4	−0.1 (3)
N1—Cu1—N4—C13	−66.9 (2)	C12—N4—C13—N5	0.2 (3)
N1ⁱ—Cu1—N4—C13	113.1 (2)	Cu1—N4—C13—N5	175.61 (17)
O3ⁱ—Cu1—N4—C13	−157.1 (2)	C12—N6—C14—C15	118.9 (3)
O3—Cu1—N4—C13	22.9 (2)	N5—N6—C14—C15	−68.1 (3)
C13—N5—N6—C12	0.0 (3)	N6—C14—C15—C16	−85.4 (3)
C13—N5—N6—C14	−174.4 (2)	C14—C15—C16—O2	0.3 (4)
Cu1—O3—N7—O5	−107.0 (4)	C14—C15—C16—C17	−178.9 (2)
Cu1—O3—N7—O4	72.1 (4)	O2—C16—C17—C18	179.1 (3)
C2—N1—C1—N3	−0.2 (3)	C15—C16—C17—C18	−1.7 (4)
Cu1—N1—C1—N3	−173.99 (16)	O2—C16—C17—C22	−0.3 (4)
N2—N3—C1—N1	0.3 (3)	C15—C16—C17—C22	179.0 (2)
C3—N3—C1—N1	175.1 (2)	C22—C17—C18—C19	0.1 (4)
N3—N2—C2—N1	0.0 (3)	C16—C17—C18—C19	−179.3 (3)
C1—N1—C2—N2	0.1 (3)	C17—C18—C19—C20	−0.2 (5)
Cu1—N1—C2—N2	174.55 (19)	C18—C19—C20—C21	0.2 (5)
C1—N3—C3—C4	137.6 (3)	C19—C20—C21—C22	−0.1 (5)
N2—N3—C3—C4	−48.0 (3)	C20—C21—C22—C17	−0.1 (5)
N3—C3—C4—C5	−177.6 (2)	C18—C17—C22—C21	0.1 (4)
C3—C4—C5—O1	7.8 (4)	C16—C17—C22—C21	179.5 (3)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···N2ⁱⁱ	0.97	2.50	3.368 (4)	148
C19—H19···O5ⁱⁱⁱ	0.93	2.56	3.291 (4)	136

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

Experimental details

Crystal data
Chemical formula	[Cu(NO₃)₂(C₁₁H₁₁N₃O)₄]
M_r	992.47
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.7742 (14), 12.472 (2), 12.498 (2)
α, β, γ (°)	102.232 (3), 100.737 (3), 104.394 (3)
V (Å³)	1110.0 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.57
Crystal size (mm)	0.24 × 0.20 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.876, 0.925
No. of measured, independent and observed [I > 2σ(I)] reflections	5737, 3905, 3295
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.105, 1.03
No. of reflections	3905
No. of parameters	313
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.34

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···N2ⁱ	0.97	2.50	3.368 (4)	148.2
C19—H19···O5ⁱⁱ	0.93	2.56	3.291 (4)	136.0

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

Acknowledgements

We acknowledge financial support by the Special Fund for Central Universities (ZXH2009D011), the Natural Science Foundation of Tianjin (09JCYBJC04200), the National Natural Science Foundation of the Civil Aviation Administration of China (61079010) and the Scientific Research Foundation of the Civil Aviation University of China (No. 2011KYS05)

References

Barnett, S. A. & Champness, N. R. (2003). Coord. Chem. Rev. 246, 145–168. Web of Science CrossRef CAS Google Scholar
Brandenburg, K. & Berndt, M. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cai, H., Guo, Y. & Li, J.-G. (2010). Acta Cryst. E66, m1605. Web of Science CSD CrossRef IUCr Journals Google Scholar
Roesky, H. W. & Andruh, M. (2003). Coord. Chem. Rev. 236, 91–119. Web of Science CrossRef CAS 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
Zaworotko, M. J. (2001). Chem. Commun. pp. 1–9. Web of Science CrossRef Google Scholar

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Volume 67| Part 10| October 2011| Page m1385

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis(nitrato-κO)tetra­kis­[1-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-1-one]copper(II)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(nitrato-κO)tetrakis[1-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-1-one]copper(II)