catena-Poly[[(dimethyl-formamide-κO)copper(II)]-bis-(μ-4-nitro-phenyl-cyanamido-κN:N)].

In the title compound, [Cu(C(7)H(4)N(3)O(2))(2)(C(3)H(7)NO)], the Cu(II) atom is five-coordinated in a distorted square-pyramidal geometry, with the N atoms in equatorial positions and the dimethyl-formamide 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 (μ1,3 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 = 460.91

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.091

S = 1.08

4874 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.99 e Å−3

Δρmin = −0.91 e Å−3

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 ▶).

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

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

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

[Cu(C7H4N3O2)2(C3H7NO)]	F(000) = 940
Mr = 460.91	Dx = 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

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

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033	w = 1/[σ2(Fo2) + (0.051P)2 + 0.8628P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.091	(Δ/σ)max = 0.017
S = 1.08	Δρmax = 0.99 e Å−3
4874 reflections	Δρmin = −0.91 e Å−3
273 parameters

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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) ; (ii) .