catena-Poly[[(dimethyl­formamide-κO)copper(II)]-bis­(μ-4-nitro­phenyl­cyanamido-κ2N1:N3)]

Chiniforoshan, H.; Jalilpour, S.; Shirinfar, B.; Khavasi, H.R.

doi:10.1107/S160053680900796X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m386

doi:10.1107/S160053680900796X

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catena-Poly[[(dimethylformamide-κO)copper(II)]-bis(μ-4-nitrophenylcyanamido-κ²N¹:N³)]

Hossein Chiniforoshan,^a ^* Soghra Jalilpour,^a Bahare Shirinfar ^a and Hamid Reza Khavasi ^b

^aDepartment of Chemistry, Isfahan University of Technology, Isfahan 84156-38111, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G.C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: chinif@cc.iut.ac.ir

(Received 9 January 2009; accepted 4 March 2009; online 11 March 2009)

In the title compound, [Cu(C₇H₄N₃O₂)₂(C₃H₇NO)], the Cu^II atom is five-coordinated in a distorted square-pyramidal geometry, with the N atoms in equatorial positions and the dimethylformamide O atom in an axial position. The dihedral angle between adjacent benzene rings is 70.33 (12)°.

Related literature

The phenylcyanamide molecule can function as bridging ligand and can coordinate to two different metallic centers by means of the nitrile and amine N atoms (μ_1,3 bonding mode), forming di- and polynuclear complexes, see: Ainscough et al. (1991 ); Brader et al. (1990 ); Crutchley (2001 ); Escuer et al. (2004 ). For the magnetic properties of coordination polymers, see: Grosshenny et al. (1996 ). For the preparation of 4-NO₂-phenylcyanamide used in the synthesis, see: Crutchley & Naklicki (1989 ).

Experimental

Crystal data

[Cu(C₇H₄N₃O₂)₂(C₃H₇NO)]
M_r = 460.91
Monoclinic, P 2₁ /c
a = 21.5103 (12) Å
b = 8.7883 (5) Å
c = 9.9195 (5) Å
β = 101.746 (4)°
V = 1835.91 (17) Å³
Z = 4
Mo Kα radiation
μ = 1.24 mm⁻¹
T = 120 K
0.50 × 0.23 × 0.15 mm

Data collection

Stoe IPDS-II diffractometer
Absorption correction: numerical with shape of crystal determined optically T_min = 0.720, T_max = 0.832
13057 measured reflections
4874 independent reflections
4496 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.091
S = 1.08
4874 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.99 e Å⁻³
Δρ_min = −0.91 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

N2—Cu1	2.0862 (13)
N5—Cu1	2.0599 (12)
Cu1—N4ⁱ	1.9648 (13)
Cu1—N1ⁱⁱ	1.9748 (13)
Cu1—O5	2.1443 (12)

N4ⁱ—Cu1—N1ⁱⁱ	154.42 (6)
N4ⁱ—Cu1—N5	90.85 (5)
N1ⁱⁱ—Cu1—N2	90.41 (5)
N5—Cu1—N2	172.66 (5)
N4ⁱ—Cu1—O5	102.75 (5)
N1ⁱⁱ—Cu1—O5	102.83 (5)
N5—Cu1—O5	92.25 (5)
N2—Cu1—O5	95.08 (5)
Symmetry codes: (i) $[x, -y-{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y-{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2005 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900796X/bq2120sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900796X/bq2120Isup2.hkl

checkCIF report

Comment top

Phenylcyanamide ligands are used in the construction of transition metal coordination complexes. The study of coordination polymeric materials holds great interest. The phenylcyanamide can function as bridging ligand and can coordinate to two different metallic centers by means of the nitrile and amine nitrogen (µ_1,3 bonding mode), forming di- and polynuclear complexes (Brader et al., 1990; Crutchley et al., 2001; Ainscough et al., 1991; Escuer et al., 2004). It can modify the solubility and crystallinety of resulting compounds and there is the different coordination in complexes. We are attempting to construct conductive inorganic polymer chains that are cross-linked by cyanamide groups to a coordination complex. Coordination polymers also hold promise as novel materials because of their magnetic properties (Grosshenny et al., 1996). More recently various aromatic cyanamide complexes have been studied by x-ray crystallography.

In the molecule of the title compound, (I), (Fig. 1) the selected bond lengths and angles are listed in Table 1. In this molecule, the {Cu(4—NO₂-pcyd)₂(DMF)}_n one-dimensional chain coordination polymer bridged by 4-NO₂-phenylcyanamide. Each copper atom has a distored square pyramidal geometry, that nitrogen atoms are in equatorial position and oxygen atom from DMF molecule is in axial position (Table 1.). The dihedral angle between adjacent phenyl rings in the polymeric chain is 70.33 (12)°.

Related literature top

The phenylcyanamide can function as bridging ligand and cancoordinate to two different metallic centers by means of the nitrile and amine nitrogen (µ_1,3 bonding mode), forming di- and polynuclear complexes, see: Ainscough et al. (1991); Brader et al. (1990); Crutchley (2001); Escuer et al. (2004). For the magnetic properties of coordination polymers, see: Grosshenny et al. (1996). For the preparation of 4-NO₂-phenylcyanamide used in the synthesis, see: Crutchley & Naklicki (1989);

Experimental top

The 4-NO2-phenylcyanamide (Crutchley et al.,1989) (0.163 gr, 0.5 mmol) dissolved in methanol (30 ml) was added slowly to a solution of copper(II) acetate monohydrate (0.998 gr, 1 mmol) in methanol (30 ml). The mixture was stirred for 4 h. The solid filtered and crystals suitable for X-ray structure determination were obtained by dissolving in DMF then diffused by n-Hexane, after 1 week.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. View of (I) with 30% probability displacement ellipsoids. Symmetry code (i): x, -y - 3/2, z - 1/2.

catena-Poly[[(dimethylformamide-κO)copper(II)]- bis(µ-4-nitrophenylcyanamido-κ²N¹:N³)] top

Crystal data top

[Cu(C₇H₄N₃O₂)₂(C₃H₇NO)]	F(000) = 940
M_r = 460.91	D_x = 1.668 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1359 reflections
a = 21.5103 (12) Å	θ = 3.0–29.3°
b = 8.7883 (5) Å	µ = 1.24 mm⁻¹
c = 9.9195 (5) Å	T = 120 K
β = 101.746 (4)°	Prism, violet
V = 1835.91 (17) Å³	0.5 × 0.23 × 0.15 mm
Z = 4

Data collection top

Stoe IPDS-II diffractometer	4496 reflections with I > 2σ(I)
rotation method scans	R_int = 0.050
Absorption correction: numerical shape of crystal determined optically	θ_max = 29.3°, θ_min = 3.0°
T_min = 0.720, T_max = 0.832	h = −29→24
13057 measured reflections	k = −10→12
4874 independent reflections	l = −13→13

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.033	w = 1/[σ²(F_o²) + (0.051P)² + 0.8628P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.091	(Δ/σ)_max = 0.017
S = 1.08	Δρ_max = 0.99 e Å⁻³
4874 reflections	Δρ_min = −0.91 e Å⁻³
273 parameters

Crystal data top

[Cu(C₇H₄N₃O₂)₂(C₃H₇NO)]	V = 1835.91 (17) Å³
M_r = 460.91	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.5103 (12) Å	µ = 1.24 mm⁻¹
b = 8.7883 (5) Å	T = 120 K
c = 9.9195 (5) Å	0.5 × 0.23 × 0.15 mm
β = 101.746 (4)°

Data collection top

Stoe IPDS-II diffractometer	4874 independent reflections
Absorption correction: numerical shape of crystal determined optically	4496 reflections with I > 2σ(I)
T_min = 0.720, T_max = 0.832	R_int = 0.050
13057 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.08	Δρ_max = 0.99 e Å⁻³
4874 reflections	Δρ_min = −0.91 e Å⁻³
273 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.

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

	x	y	z	U_iso*/U_eq
C1	0.18470 (7)	−0.78476 (17)	0.48486 (14)	0.0134 (3)
C2	0.11109 (7)	−0.85879 (17)	0.61210 (15)	0.0134 (3)
C3	0.06225 (7)	−0.77637 (19)	0.52815 (15)	0.0170 (3)
H3	0.0717	−0.7132	0.4599	0.02*
C4	−0.00005 (7)	−0.78755 (19)	0.54535 (16)	0.0187 (3)
H4	−0.0323	−0.7327	0.4893	0.022*
C5	−0.01325 (7)	−0.8821 (2)	0.64786 (16)	0.0179 (3)
C6	0.03397 (8)	−0.96827 (18)	0.73088 (16)	0.0177 (3)
H6	0.0239	−1.0325	0.7978	0.021*
C7	0.09602 (7)	−0.95722 (17)	0.71271 (15)	0.0155 (3)
H7	0.1278	−1.015	0.7671	0.019*
C8	0.31962 (7)	−0.74093 (18)	1.03158 (14)	0.0140 (3)
C9	0.39374 (7)	−0.82569 (17)	0.90993 (15)	0.0142 (3)
C10	0.41040 (7)	−0.94717 (18)	0.83254 (15)	0.0156 (3)
H10	0.3799	−1.0178	0.7932	0.019*
C11	0.47252 (7)	−0.96186 (19)	0.81480 (15)	0.0179 (3)
H11	0.4839	−1.0419	0.7634	0.021*
C12	0.51748 (8)	−0.8551 (2)	0.87497 (16)	0.0186 (3)
C13	0.50288 (7)	−0.7369 (2)	0.95631 (16)	0.0192 (3)
H13	0.534	−0.6688	0.9982	0.023*
C14	0.44059 (7)	−0.72297 (19)	0.97349 (15)	0.0170 (3)
H14	0.4299	−0.6448	1.0277	0.02*
C15	0.23643 (8)	−1.18081 (18)	0.70530 (16)	0.0164 (3)
H15	0.2162	−1.1469	0.6187	0.02*
C16	0.27640 (9)	−1.3914 (2)	0.85538 (18)	0.0239 (3)
H16A	0.2471	−1.4544	0.8914	0.029*
H16B	0.2907	−1.3101	0.9187	0.029*
H16C	0.3121	−1.4514	0.8431	0.029*
C17	0.22428 (9)	−1.4360 (2)	0.61151 (18)	0.0242 (3)
H17C	0.195	−1.5073	0.6375	0.029*
H17B	0.2605	−1.4896	0.5928	0.029*
H17A	0.2038	−1.382	0.5305	0.029*
N1	0.19773 (6)	−0.73209 (16)	0.38708 (13)	0.0159 (2)
N2	0.17467 (6)	−0.84608 (14)	0.59891 (13)	0.0133 (2)
N3	−0.07813 (7)	−0.8905 (2)	0.67009 (16)	0.0245 (3)
N4	0.30602 (6)	−0.68183 (17)	1.12639 (13)	0.0169 (3)
N5	0.32972 (6)	−0.80866 (16)	0.92140 (12)	0.0136 (2)
N6	0.58231 (7)	−0.8682 (2)	0.85134 (15)	0.0249 (3)
N7	0.24485 (6)	−1.32833 (16)	0.72334 (14)	0.0166 (3)
Cu1	0.252435 (8)	−0.842098 (19)	0.763487 (17)	0.01030 (7)
O1	−0.11924 (6)	−0.8137 (2)	0.59671 (16)	0.0360 (3)
O2	−0.08874 (8)	−0.9731 (2)	0.7622 (2)	0.0497 (5)
O3	0.61904 (7)	−0.7620 (2)	0.88752 (16)	0.0380 (4)
O4	0.59667 (7)	−0.9839 (2)	0.79478 (16)	0.0379 (4)
O5	0.25389 (6)	−1.08324 (13)	0.79693 (11)	0.0182 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0091 (6)	0.0152 (6)	0.0141 (6)	−0.0002 (5)	−0.0015 (5)	−0.0010 (5)
C2	0.0118 (6)	0.0143 (6)	0.0137 (6)	−0.0026 (5)	0.0017 (5)	−0.0023 (5)
C3	0.0150 (7)	0.0208 (7)	0.0146 (6)	0.0011 (5)	0.0017 (5)	0.0014 (5)
C4	0.0131 (7)	0.0228 (8)	0.0189 (6)	0.0024 (6)	0.0005 (5)	−0.0020 (6)
C5	0.0116 (6)	0.0208 (7)	0.0219 (7)	−0.0027 (6)	0.0047 (5)	−0.0059 (6)
C6	0.0162 (7)	0.0176 (7)	0.0204 (7)	−0.0046 (5)	0.0062 (5)	−0.0007 (5)
C7	0.0139 (6)	0.0158 (6)	0.0163 (6)	−0.0025 (5)	0.0019 (5)	0.0004 (5)
C8	0.0089 (6)	0.0183 (7)	0.0135 (6)	−0.0012 (5)	−0.0009 (5)	0.0010 (5)
C9	0.0115 (6)	0.0182 (7)	0.0125 (6)	0.0023 (5)	0.0015 (5)	0.0023 (5)
C10	0.0134 (6)	0.0177 (7)	0.0145 (6)	0.0020 (5)	0.0005 (5)	−0.0002 (5)
C11	0.0163 (7)	0.0224 (7)	0.0147 (6)	0.0060 (6)	0.0029 (5)	0.0012 (5)
C12	0.0116 (6)	0.0271 (8)	0.0173 (7)	0.0029 (6)	0.0035 (5)	0.0051 (6)
C13	0.0133 (6)	0.0246 (8)	0.0190 (7)	−0.0025 (6)	0.0019 (5)	0.0015 (6)
C14	0.0144 (7)	0.0204 (7)	0.0159 (6)	0.0002 (5)	0.0025 (5)	−0.0024 (5)
C15	0.0183 (7)	0.0142 (7)	0.0169 (6)	−0.0004 (5)	0.0039 (5)	0.0002 (5)
C16	0.0293 (8)	0.0163 (7)	0.0251 (8)	0.0047 (6)	0.0031 (6)	0.0053 (6)
C17	0.0303 (9)	0.0170 (7)	0.0265 (8)	−0.0018 (6)	0.0089 (7)	−0.0079 (6)
N1	0.0104 (5)	0.0230 (7)	0.0139 (5)	−0.0003 (5)	0.0014 (4)	0.0018 (5)
N2	0.0100 (5)	0.0181 (6)	0.0110 (5)	−0.0018 (4)	0.0006 (4)	0.0006 (4)
N3	0.0151 (6)	0.0283 (8)	0.0312 (7)	−0.0031 (6)	0.0074 (5)	−0.0066 (6)
N4	0.0105 (5)	0.0263 (7)	0.0130 (5)	−0.0018 (5)	−0.0001 (4)	−0.0031 (5)
N5	0.0093 (5)	0.0191 (6)	0.0119 (5)	0.0002 (4)	0.0007 (4)	−0.0023 (4)
N6	0.0147 (6)	0.0396 (9)	0.0211 (6)	0.0052 (6)	0.0049 (5)	0.0051 (6)
N7	0.0183 (6)	0.0130 (6)	0.0186 (6)	−0.0008 (4)	0.0039 (5)	−0.0012 (4)
Cu1	0.00955 (10)	0.01191 (10)	0.00912 (10)	−0.00041 (6)	0.00118 (6)	−0.00033 (5)
O1	0.0144 (6)	0.0544 (10)	0.0386 (8)	0.0052 (6)	0.0040 (5)	−0.0007 (7)
O2	0.0246 (7)	0.0595 (11)	0.0711 (12)	0.0005 (7)	0.0246 (8)	0.0261 (10)
O3	0.0161 (6)	0.0527 (10)	0.0463 (8)	−0.0059 (6)	0.0087 (6)	−0.0026 (7)
O4	0.0244 (7)	0.0487 (9)	0.0443 (8)	0.0094 (7)	0.0154 (6)	−0.0049 (7)
O5	0.0248 (6)	0.0119 (5)	0.0169 (5)	−0.0014 (4)	0.0017 (4)	−0.0005 (4)

Geometric parameters (Å, º) top

C1—N1	1.160 (2)	C13—C14	1.390 (2)
C1—N2	1.3099 (18)	C13—H13	0.93
C2—C3	1.402 (2)	C14—H14	0.93
C2—N2	1.4046 (19)	C15—O5	1.250 (2)
C2—C7	1.408 (2)	C15—N7	1.316 (2)
C3—C4	1.388 (2)	C15—H15	0.93
C3—H3	0.93	C16—N7	1.457 (2)
C4—C5	1.387 (2)	C16—H16A	0.96
C4—H4	0.93	C16—H16B	0.96
C5—C6	1.394 (2)	C16—H16C	0.96
C5—N3	1.458 (2)	C17—N7	1.457 (2)
C6—C7	1.386 (2)	C17—H17C	0.96
C6—H6	0.93	C17—H17B	0.96
C7—H7	0.93	C17—H17A	0.96
C8—N4	1.163 (2)	N1—Cu1ⁱ	1.9748 (13)
C8—N5	1.3010 (19)	N2—Cu1	2.0862 (13)
C9—C14	1.403 (2)	N3—O2	1.224 (2)
C9—C10	1.403 (2)	N3—O1	1.227 (2)
C9—N5	1.4126 (19)	N4—Cu1ⁱⁱ	1.9648 (13)
C10—C11	1.389 (2)	N5—Cu1	2.0599 (12)
C10—H10	0.93	N6—O3	1.229 (2)
C11—C12	1.392 (2)	N6—O4	1.230 (2)
C11—H11	0.93	Cu1—N4ⁱ	1.9648 (13)
C12—C13	1.390 (2)	Cu1—N1ⁱⁱ	1.9748 (13)
C12—N6	1.465 (2)	Cu1—O5	2.1443 (12)

N1—C1—N2	175.56 (15)	N7—C16—H16A	109.5
C3—C2—N2	121.98 (13)	N7—C16—H16B	109.5
C3—C2—C7	119.06 (14)	H16A—C16—H16B	109.5
N2—C2—C7	118.96 (13)	N7—C16—H16C	109.5
C4—C3—C2	121.05 (14)	H16A—C16—H16C	109.5
C4—C3—H3	119.5	H16B—C16—H16C	109.5
C2—C3—H3	119.5	N7—C17—H17C	109.5
C5—C4—C3	118.64 (14)	N7—C17—H17B	109.5
C5—C4—H4	120.7	H17C—C17—H17B	109.5
C3—C4—H4	120.7	N7—C17—H17A	109.5
C4—C5—C6	121.70 (14)	H17C—C17—H17A	109.5
C4—C5—N3	119.07 (15)	H17B—C17—H17A	109.5
C6—C5—N3	119.22 (15)	C1—N1—Cu1ⁱ	158.01 (12)
C7—C6—C5	119.36 (14)	C1—N2—C2	116.60 (12)
C7—C6—H6	120.3	C1—N2—Cu1	114.97 (10)
C5—C6—H6	120.3	C2—N2—Cu1	124.69 (9)
C6—C7—C2	120.15 (14)	O2—N3—O1	123.22 (16)
C6—C7—H7	119.9	O2—N3—C5	118.16 (16)
C2—C7—H7	119.9	O1—N3—C5	118.63 (16)
N4—C8—N5	175.15 (15)	C8—N4—Cu1ⁱⁱ	152.54 (13)
C14—C9—C10	119.68 (14)	C8—N5—C9	116.64 (12)
C14—C9—N5	121.22 (13)	C8—N5—Cu1	117.20 (10)
C10—C9—N5	119.09 (14)	C9—N5—Cu1	124.94 (9)
C11—C10—C9	119.96 (15)	O3—N6—O4	123.70 (16)
C11—C10—H10	120	O3—N6—C12	118.03 (16)
C9—C10—H10	120	O4—N6—C12	118.26 (16)
C10—C11—C12	119.05 (14)	C15—N7—C17	121.62 (15)
C10—C11—H11	120.5	C15—N7—C16	121.55 (14)
C12—C11—H11	120.5	C17—N7—C16	116.82 (14)
C13—C12—C11	122.23 (14)	N4ⁱ—Cu1—N1ⁱⁱ	154.42 (6)
C13—C12—N6	119.11 (15)	N4ⁱ—Cu1—N5	90.85 (5)
C11—C12—N6	118.65 (15)	N1ⁱⁱ—Cu1—N5	88.36 (5)
C14—C13—C12	118.31 (15)	N4ⁱ—Cu1—N2	87.13 (5)
C14—C13—H13	120.8	N1ⁱⁱ—Cu1—N2	90.41 (5)
C12—C13—H13	120.8	N5—Cu1—N2	172.66 (5)
C13—C14—C9	120.69 (14)	N4ⁱ—Cu1—O5	102.75 (5)
C13—C14—H14	119.7	N1ⁱⁱ—Cu1—O5	102.83 (5)
C9—C14—H14	119.7	N5—Cu1—O5	92.25 (5)
O5—C15—N7	124.33 (15)	N2—Cu1—O5	95.08 (5)
O5—C15—H15	117.8	C15—O5—Cu1	124.92 (11)
N7—C15—H15	117.8

N2—C2—C3—C4	−178.27 (14)	C14—C9—N5—C8	−27.7 (2)
C7—C2—C3—C4	1.7 (2)	C10—C9—N5—C8	152.76 (14)
C2—C3—C4—C5	0.1 (2)	C14—C9—N5—Cu1	139.25 (12)
C3—C4—C5—C6	−1.6 (2)	C10—C9—N5—Cu1	−40.26 (19)
C3—C4—C5—N3	177.78 (15)	C13—C12—N6—O3	−10.4 (2)
C4—C5—C6—C7	1.3 (2)	C11—C12—N6—O3	169.52 (16)
N3—C5—C6—C7	−178.12 (14)	C13—C12—N6—O4	170.58 (16)
C5—C6—C7—C2	0.6 (2)	C11—C12—N6—O4	−9.5 (2)
C3—C2—C7—C6	−2.0 (2)	O5—C15—N7—C17	−178.97 (15)
N2—C2—C7—C6	177.94 (14)	O5—C15—N7—C16	−0.3 (3)
C14—C9—C10—C11	−2.5 (2)	C8—N5—Cu1—N4ⁱ	147.21 (12)
N5—C9—C10—C11	177.06 (13)	C9—N5—Cu1—N4ⁱ	−19.70 (13)
C9—C10—C11—C12	0.2 (2)	C8—N5—Cu1—N1ⁱⁱ	−7.22 (12)
C10—C11—C12—C13	2.2 (2)	C9—N5—Cu1—N1ⁱⁱ	−174.13 (13)
C10—C11—C12—N6	−177.70 (14)	C8—N5—Cu1—O5	−110.00 (12)
C11—C12—C13—C14	−2.2 (2)	C9—N5—Cu1—O5	83.09 (13)
N6—C12—C13—C14	177.69 (14)	C1—N2—Cu1—N4ⁱ	−21.30 (11)
C12—C13—C14—C9	−0.1 (2)	C2—N2—Cu1—N4ⁱ	−178.68 (12)
C10—C9—C14—C13	2.5 (2)	C1—N2—Cu1—N1ⁱⁱ	133.23 (11)
N5—C9—C14—C13	−177.06 (14)	C2—N2—Cu1—N1ⁱⁱ	−24.15 (12)
C3—C2—N2—C1	−16.4 (2)	C1—N2—Cu1—O5	−123.85 (11)
C7—C2—N2—C1	163.60 (14)	C2—N2—Cu1—O5	78.76 (12)
C3—C2—N2—Cu1	140.62 (12)	N7—C15—O5—Cu1	171.10 (11)
C7—C2—N2—Cu1	−39.34 (18)	N4ⁱ—Cu1—O5—C15	−57.95 (14)
C4—C5—N3—O2	−179.12 (18)	N1ⁱⁱ—Cu1—O5—C15	121.84 (13)
C6—C5—N3—O2	0.3 (3)	N5—Cu1—O5—C15	−149.33 (13)
C4—C5—N3—O1	0.3 (2)	N2—Cu1—O5—C15	30.25 (13)
C6—C5—N3—O1	179.73 (16)

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

Experimental details

Crystal data
Chemical formula	[Cu(C₇H₄N₃O₂)₂(C₃H₇NO)]
M_r	460.91
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	21.5103 (12), 8.7883 (5), 9.9195 (5)
β (°)	101.746 (4)
V (Å³)	1835.91 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.24
Crystal size (mm)	0.5 × 0.23 × 0.15

Data collection
Diffractometer	Stoe IPDS-II diffractometer
Absorption correction	Numerical shape of crystal determined optically
T_min, T_max	0.720, 0.832
No. of measured, independent and observed [I > 2σ(I)] reflections	13057, 4874, 4496
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.091, 1.08
No. of reflections	4874
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.99, −0.91

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXTL (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

N2—Cu1	2.0862 (13)	Cu1—N1ⁱⁱ	1.9748 (13)
N5—Cu1	2.0599 (12)	Cu1—O5	2.1443 (12)
Cu1—N4ⁱ	1.9648 (13)

N4ⁱ—Cu1—N1ⁱⁱ	154.42 (6)	N4ⁱ—Cu1—O5	102.75 (5)
N4ⁱ—Cu1—N5	90.85 (5)	N1ⁱⁱ—Cu1—O5	102.83 (5)
N1ⁱⁱ—Cu1—N2	90.41 (5)	N5—Cu1—O5	92.25 (5)
N5—Cu1—N2	172.66 (5)	N2—Cu1—O5	95.08 (5)

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

Acknowledgements

The authors acknowledge financial support from Isfahan University of Technology.

References

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