catena-Poly[[(dimethyl­formamide-κO)cobalt(II)]-bis­[μ-(4-nitro­phenyl)­cyanamido]-κ2N1:N3;κ2N3:N1]

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

doi:10.1107/S160053681000557X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m331

doi:10.1107/S160053681000557X

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catena-Poly[[(dimethylformamide-κO)cobalt(II)]-bis[μ-(4-nitrophenyl)cyanamido]-κ²N¹:N³;κ²N³:N¹]

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

^aDepartment of Chemistry, Isfahan University of Technology, Isfahan 84456-38111, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: chinif@cc.iut.ac.ir

(Received 4 January 2010; accepted 10 February 2010; online 24 February 2010)

In the title coordination polymer, [Co(C₇H₄N₃O₂)₂(C₃H₇NO)]_n, the Co^II atom is five-coordinated in a distorted square-pyramidal CoON₄ geometry with the O atom from a dimethylformamide molecule in an equatorial position. The bridging phenylcyanamide anions generate an infinite chain propagating in [001].

Related literature

For background to models of ligand bonding, see: Storhoff & Lewis (1977 ); Chisholm et al. (1987 ); Crutchley et al. (1999 ). For related structures, see: Escuer et al. (2003a ,b , 2004 ); Chiniforoshan et al. (2009 ). For further synthetic details, see: Crutchley & Naklicki (1989 ).

Experimental

Crystal data

[Co(C₇H₄N₃O₂)₂(C₃H₇NO)]
M_r = 456.29
Monoclinic, P 2₁ /c
a = 21.8692 (16) Å
b = 8.8517 (6) Å
c = 9.9827 (8) Å
β = 100.151 (6)°
V = 1902.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.95 mm⁻¹
T = 120 K
0.30 × 0.12 × 0.10 mm

Data collection

STOE IPDS II diffractometer
Absorption correction: numerical [optical; X-RED and X-SHAPE (Stoe & Cie, 2005 )] T_min = 0.740, T_max = 0.800
22258 measured reflections
5131 independent reflections
4161 reflections with I > 2σ(I)
R_int = 0.074

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.104
S = 1.20
5131 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.70 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O5	1.9807 (19)
Co1—N3	1.994 (2)
Co1—N5	2.198 (2)
Co1—N6ⁱ	1.971 (2)
Co1—N2ⁱ	2.2896 (19)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000557X/hb5302sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681000557X/hb5302Isup2.hkl

checkCIF report

Comment top

Phenylcyanamide ligands (Pcyd) are interesting and practically ligands from the synthetic and magnetic point of view. Recently, we have reported the first magnetic measurements on systems with different dimensionality containing the MnII-(NCN)2- unit (Escuer et al., 2003a,b) the cyanamido group(NCN) being coordinated in the end-to-end mode. From the synthetic point of view, pcyd ligands offer a wide range of possibilities based on the use different X-pcyd derivatives which can coordinate properties of the two nitrogen atoms: one N-nitrile, which coordinate preferently and one N-amide atom, with characteristic bond parameters in each case (Escuer et al., 2004). Following our work with this family of ligands, we now report four new Co^II-Xpcyd compounds (using 4-nitro,4-fluoro,4-chloro,4-bromophenylcyanamide) in combination with the dimethylformamide ligand. These compounds contain the unusual end-to-end phenyl-cyanamide bridge and give supramolecular one dimensional network by means of H-bonds involving the N-amid atoms of the phenylcyanamide ligands. Side-on coordination of a nitrile group is extremely rare (Storhoff & Lewis, 1977) but is more common for cyanamide ligands due to the participation of the nitrile lone pair in bridging interaction (Chisholm et al., 1987). We are attempting to construct conductive polymer chains that are cross-linked by cyanamide groups to a coordination complex. Conductivity within this linked system will arise provided the polymer p-pi orbitals and the metal dp orbital are both symmetry and energy matched (Crutchley et al., 1999). More recently various aromatic cyanamide complexes have been studied by x-ray crystallography (Chiniforoshan et al., 2009).

We report here the synthesis and crystal structure of the title complex, (I).

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 {Co(4—NO₂-pcyd)₂(DMF)}_n one-dimensional chain coordination polymer bridged by 4-NO₂-phenylcyanamide. Each cobalt atom has a distored square pyramidal geometry, that nitrogen atoms are in equatirial position and oxygen atom from DMF molecules is in axial position, Table 1. The dihedral angle between adjacent phenyl rings in the polymeric chain is 89.02 (10) °.

Related literature top

For background to models of ligand bonding, see: Storhoff & Lewis (1977); Chisholm et al. (1987); Crutchley et al. (1999). For related structures, see: Escuer et al. (2003a,b, 2004); Chiniforoshan et al. (2009). For further synthetic details, see: Crutchley & Naklicki (1989).

Experimental top

4-Nitrophenylcyanamide (Crutchley et al.,1989) (0.326 g, 0.5 mmol) was dissolved in methanol (25 ml) and was added slowly to a solution of cobalt(II) acetate (0.249 g, 0.25 mmol) in methanol (25 ml). The mixture was stirred for 5 h. The resulting solid was filtered off and violet needles of (I) obtained by dissolving in DMF then diffused by acetonitrile after 2 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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. View of (I) (30% probability displacement ellipsoids), (i) x,-y+1/2,z-1/2.

catena-Poly[[(dimethylformamide-κO)cobalt(II)]-bis[µ-(4- nitrophenyl)cyanamido]- κ²N¹:N³;κ²N³:N¹] top

Crystal data top

[Co(C₇H₄N₃O₂)₂(C₃H₇NO)]	F(000) = 932
M_r = 456.29	D_x = 1.593 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 987 reflections
a = 21.8692 (16) Å	θ = 1.9–29.3°
b = 8.8517 (6) Å	µ = 0.95 mm⁻¹
c = 9.9827 (8) Å	T = 120 K
β = 100.151 (6)°	Needle, violet
V = 1902.2 (2) Å³	0.3 × 0.12 × 0.1 mm
Z = 4

Data collection top

STOE IPDS II diffractometer	5131 independent reflections
Radiation source: fine-focus sealed tube	4161 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
rotation method scans	θ_max = 29.3°, θ_min = 1.9°
Absorption correction: numerical [optical; X-RED and X-SHAPE (Stoe & Cie, 2005)]	h = −30→30
T_min = 0.740, T_max = 0.800	k = −12→12
22258 measured reflections	l = −13→13

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.20	w = 1/[σ²(F_o²) + (0.0287P)² + 1.1087P] where P = (F_o² + 2F_c²)/3
5131 reflections	(Δ/σ)_max = 0.023
273 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

[Co(C₇H₄N₃O₂)₂(C₃H₇NO)]	V = 1902.2 (2) Å³
M_r = 456.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.8692 (16) Å	µ = 0.95 mm⁻¹
b = 8.8517 (6) Å	T = 120 K
c = 9.9827 (8) Å	0.3 × 0.12 × 0.1 mm
β = 100.151 (6)°

Data collection top

STOE IPDS II diffractometer	5131 independent reflections
Absorption correction: numerical [optical; X-RED and X-SHAPE (Stoe & Cie, 2005)]	4161 reflections with I > 2σ(I)
T_min = 0.740, T_max = 0.800	R_int = 0.074
22258 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.20	Δρ_max = 0.35 e Å⁻³
5131 reflections	Δρ_min = −0.70 e Å⁻³
273 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.40669 (12)	0.4544 (3)	0.2890 (2)	0.0367 (5)
H1	0.3765	0.5107	0.2332	0.044*
C2	0.46736 (13)	0.4600 (3)	0.2693 (3)	0.0418 (6)
H2	0.4782	0.5200	0.2007	0.050*
C3	0.51209 (12)	0.3757 (3)	0.3524 (3)	0.0411 (6)
C4	0.49727 (12)	0.2877 (3)	0.4559 (3)	0.0432 (6)
H4	0.5279	0.2326	0.5116	0.052*
C5	0.43659 (12)	0.2821 (3)	0.4759 (2)	0.0392 (6)
H5	0.4264	0.2228	0.5457	0.047*
C6	0.39001 (10)	0.3643 (3)	0.3927 (2)	0.0299 (4)
C7	0.31504 (10)	0.2978 (3)	0.5177 (2)	0.0295 (4)
C8	0.08686 (12)	0.0534 (3)	0.6636 (2)	0.0391 (6)
H8	0.1158	−0.0163	0.7060	0.047*
C9	0.02663 (13)	0.0479 (4)	0.6859 (3)	0.0455 (7)
H9	0.0145	−0.0259	0.7420	0.055*
C10	−0.01572 (12)	0.1535 (4)	0.6238 (3)	0.0457 (7)
C11	0.00043 (13)	0.2613 (4)	0.5372 (3)	0.0479 (7)
H11	−0.0289	0.3300	0.4948	0.057*
C12	0.06063 (13)	0.2663 (3)	0.5141 (3)	0.0421 (6)
H12	0.0720	0.3388	0.4557	0.051*
C13	0.10495 (11)	0.1630 (3)	0.5777 (2)	0.0320 (5)
C14	0.17962 (11)	0.2310 (3)	0.4517 (2)	0.0329 (5)
C15	0.26634 (13)	−0.1792 (3)	0.7963 (3)	0.0404 (6)
H15	0.2886	−0.1460	0.8791	0.049*
C16	0.22430 (18)	−0.3852 (4)	0.6534 (3)	0.0590 (8)
H16A	0.2522	−0.4419	0.6084	0.071*
H16B	0.2065	−0.3041	0.5956	0.071*
H16C	0.1918	−0.4503	0.6726	0.071*
C17	0.28133 (19)	−0.4310 (4)	0.8862 (4)	0.0623 (9)
H17A	0.2471	−0.4804	0.9163	0.075*
H17B	0.3056	−0.3781	0.9612	0.075*
H17C	0.3068	−0.5050	0.8522	0.075*
Co1	0.246533 (14)	0.14018 (3)	0.72734 (3)	0.02718 (9)
N1	0.57585 (12)	0.3801 (4)	0.3298 (3)	0.0590 (7)
N2	0.32762 (9)	0.3587 (2)	0.40707 (17)	0.0315 (4)
N3	0.29935 (9)	0.2463 (2)	0.61327 (19)	0.0341 (4)
N4	−0.07929 (13)	0.1482 (4)	0.6502 (3)	0.0655 (8)
N5	0.16710 (9)	0.1668 (2)	0.56040 (18)	0.0331 (4)
N6	0.19618 (10)	0.2829 (3)	0.3580 (2)	0.0429 (5)
N7	0.25790 (11)	−0.3243 (2)	0.7787 (2)	0.0417 (5)
O1	0.61519 (11)	0.3055 (4)	0.4033 (3)	0.0845 (9)
O2	0.58758 (13)	0.4571 (5)	0.2362 (4)	0.1081 (12)
O3	−0.11534 (13)	0.2481 (5)	0.6018 (3)	0.0965 (11)
O4	−0.09355 (14)	0.0446 (5)	0.7210 (3)	0.1003 (11)
O5	0.24632 (10)	−0.0826 (2)	0.70889 (18)	0.0443 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0355 (12)	0.0426 (14)	0.0319 (12)	−0.0053 (11)	0.0057 (9)	0.0042 (10)
C2	0.0403 (14)	0.0475 (15)	0.0397 (14)	−0.0138 (12)	0.0128 (11)	−0.0023 (11)
C3	0.0308 (12)	0.0495 (15)	0.0439 (14)	−0.0093 (11)	0.0090 (10)	−0.0164 (12)
C4	0.0332 (13)	0.0552 (17)	0.0398 (14)	0.0041 (12)	0.0024 (10)	−0.0030 (12)
C5	0.0384 (13)	0.0484 (15)	0.0308 (12)	0.0026 (11)	0.0063 (10)	0.0051 (11)
C6	0.0299 (10)	0.0337 (11)	0.0258 (10)	−0.0057 (10)	0.0040 (8)	−0.0036 (9)
C7	0.0275 (10)	0.0345 (11)	0.0253 (10)	−0.0014 (9)	0.0014 (8)	−0.0020 (9)
C8	0.0400 (14)	0.0454 (15)	0.0327 (12)	−0.0077 (11)	0.0083 (10)	0.0024 (10)
C9	0.0438 (15)	0.0599 (18)	0.0349 (13)	−0.0200 (13)	0.0126 (11)	−0.0042 (12)
C10	0.0331 (12)	0.071 (2)	0.0344 (12)	−0.0112 (13)	0.0104 (10)	−0.0166 (13)
C11	0.0357 (14)	0.067 (2)	0.0403 (14)	0.0050 (13)	0.0050 (11)	−0.0051 (13)
C12	0.0382 (14)	0.0554 (17)	0.0331 (13)	−0.0019 (12)	0.0073 (10)	0.0057 (11)
C13	0.0306 (11)	0.0429 (14)	0.0223 (10)	−0.0048 (10)	0.0038 (8)	−0.0019 (9)
C14	0.0255 (11)	0.0475 (14)	0.0250 (11)	−0.0020 (10)	0.0021 (8)	0.0006 (9)
C15	0.0488 (15)	0.0371 (13)	0.0353 (13)	−0.0011 (11)	0.0070 (11)	−0.0001 (9)
C16	0.068 (2)	0.0443 (17)	0.065 (2)	−0.0063 (15)	0.0124 (16)	−0.0074 (14)
C17	0.081 (3)	0.0446 (17)	0.063 (2)	−0.0005 (17)	0.0191 (18)	0.0159 (15)
Co1	0.03239 (15)	0.02822 (15)	0.02268 (13)	0.00103 (14)	0.00971 (10)	0.00032 (12)
N1	0.0367 (13)	0.077 (2)	0.0663 (17)	−0.0085 (13)	0.0166 (12)	−0.0189 (15)
N2	0.0314 (9)	0.0402 (10)	0.0232 (8)	−0.0030 (9)	0.0053 (7)	0.0037 (8)
N3	0.0279 (10)	0.0477 (12)	0.0263 (9)	−0.0028 (8)	0.0037 (7)	0.0051 (8)
N4	0.0382 (14)	0.108 (3)	0.0527 (15)	−0.0140 (17)	0.0163 (12)	−0.0224 (17)
N5	0.0303 (9)	0.0470 (12)	0.0226 (9)	−0.0016 (8)	0.0062 (7)	0.0051 (8)
N6	0.0295 (10)	0.0722 (16)	0.0268 (10)	−0.0046 (10)	0.0046 (8)	0.0128 (10)
N7	0.0458 (12)	0.0328 (11)	0.0499 (12)	−0.0012 (10)	0.0180 (10)	0.0008 (9)
O1	0.0370 (12)	0.122 (3)	0.094 (2)	0.0105 (15)	0.0106 (13)	−0.0062 (18)
O2	0.0537 (17)	0.154 (3)	0.128 (3)	−0.0070 (18)	0.0467 (18)	0.039 (2)
O3	0.0409 (14)	0.154 (3)	0.097 (2)	0.0129 (17)	0.0192 (14)	−0.003 (2)
O4	0.0613 (17)	0.146 (3)	0.105 (2)	−0.0246 (19)	0.0463 (16)	0.010 (2)
O5	0.0588 (12)	0.0305 (8)	0.0408 (10)	0.0021 (8)	0.0012 (9)	0.0004 (7)

Geometric parameters (Å, º) top

C1—C2	1.376 (4)	C13—N5	1.400 (3)
C1—C6	1.405 (3)	C14—N6	1.157 (3)
C1—H1	0.9300	C14—N5	1.296 (3)
C2—C3	1.385 (4)	C15—O5	1.245 (3)
C2—H2	0.9300	C15—N7	1.305 (3)
C3—C4	1.377 (4)	C15—H15	0.9300
C3—N1	1.452 (3)	C16—N7	1.440 (4)
C4—C5	1.377 (4)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C6	1.400 (3)	C16—H16C	0.9600
C5—H5	0.9300	C17—N7	1.453 (4)
C6—N2	1.398 (3)	C17—H17A	0.9600
C7—N3	1.162 (3)	C17—H17B	0.9600
C7—N2	1.301 (3)	C17—H17C	0.9600
C8—C9	1.375 (4)	Co1—O5	1.9807 (19)
C8—C13	1.397 (3)	Co1—N3	1.994 (2)
C8—H8	0.9300	Co1—N5	2.198 (2)
C9—C10	1.383 (4)	Co1—N6ⁱ	1.971 (2)
C9—H9	0.9300	Co1—N2ⁱ	2.2896 (19)
C10—C11	1.375 (4)	N1—O2	1.220 (4)
C10—N4	1.461 (3)	N1—O1	1.222 (4)
C11—C12	1.377 (4)	N2—Co1ⁱⁱ	2.2896 (19)
C11—H11	0.9300	N4—O3	1.226 (5)
C12—C13	1.400 (4)	N4—O4	1.231 (4)
C12—H12	0.9300	N6—Co1ⁱⁱ	1.971 (2)

C2—C1—C6	120.5 (2)	N7—C16—H16A	109.5
C2—C1—H1	119.7	N7—C16—H16B	109.5
C6—C1—H1	119.7	H16A—C16—H16B	109.5
C1—C2—C3	119.5 (2)	N7—C16—H16C	109.5
C1—C2—H2	120.3	H16A—C16—H16C	109.5
C3—C2—H2	120.3	H16B—C16—H16C	109.5
C4—C3—C2	121.3 (2)	N7—C17—H17A	109.5
C4—C3—N1	119.4 (3)	N7—C17—H17B	109.5
C2—C3—N1	119.2 (3)	H17A—C17—H17B	109.5
C3—C4—C5	119.3 (3)	N7—C17—H17C	109.5
C3—C4—H4	120.3	H17A—C17—H17C	109.5
C5—C4—H4	120.3	H17B—C17—H17C	109.5
C4—C5—C6	120.9 (2)	N6ⁱ—Co1—O5	114.40 (10)
C4—C5—H5	119.5	N6ⁱ—Co1—N3	131.52 (10)
C6—C5—H5	119.5	O5—Co1—N3	114.07 (9)
N2—C6—C5	122.8 (2)	N6ⁱ—Co1—N5	90.32 (8)
N2—C6—C1	118.7 (2)	O5—Co1—N5	92.72 (8)
C5—C6—C1	118.4 (2)	N3—Co1—N5	88.66 (8)
N3—C7—N2	175.0 (2)	N6ⁱ—Co1—N2ⁱ	85.75 (8)
C9—C8—C13	120.4 (3)	O5—Co1—N2ⁱ	93.78 (8)
C9—C8—H8	119.8	N3—Co1—N2ⁱ	89.94 (8)
C13—C8—H8	119.8	N5—Co1—N2ⁱ	173.35 (8)
C8—C9—C10	119.3 (3)	O2—N1—O1	122.8 (3)
C8—C9—H9	120.4	O2—N1—C3	118.1 (3)
C10—C9—H9	120.4	O1—N1—C3	119.1 (3)
C11—C10—C9	121.7 (2)	C7—N2—C6	117.25 (19)
C11—C10—N4	119.6 (3)	C7—N2—Co1ⁱⁱ	114.63 (15)
C9—C10—N4	118.7 (3)	C6—N2—Co1ⁱⁱ	123.69 (13)
C10—C11—C12	119.1 (3)	C7—N3—Co1	159.71 (19)
C10—C11—H11	120.4	O3—N4—O4	123.6 (3)
C12—C11—H11	120.4	O3—N4—C10	118.2 (3)
C11—C12—C13	120.6 (3)	O4—N4—C10	118.2 (3)
C11—C12—H12	119.7	C14—N5—C13	117.8 (2)
C13—C12—H12	119.7	C14—N5—Co1	115.24 (16)
C8—C13—C12	118.9 (2)	C13—N5—Co1	123.95 (14)
C8—C13—N5	118.6 (2)	C14—N6—Co1ⁱⁱ	164.6 (2)
C12—C13—N5	122.5 (2)	C15—N7—C16	121.6 (3)
N6—C14—N5	173.8 (3)	C15—N7—C17	121.1 (3)
O5—C15—N7	123.9 (3)	C16—N7—C17	117.3 (3)
O5—C15—H15	118.0	C15—O5—Co1	128.61 (18)
N7—C15—H15	118.0

C6—C1—C2—C3	0.2 (4)	C1—C6—N2—Co1ⁱⁱ	37.3 (3)
C1—C2—C3—C4	−0.9 (4)	N6ⁱ—Co1—N3—C7	−104.7 (6)
C1—C2—C3—N1	179.0 (2)	O5—Co1—N3—C7	76.9 (6)
C2—C3—C4—C5	0.8 (4)	N5—Co1—N3—C7	−15.5 (6)
N1—C3—C4—C5	−179.1 (3)	N2ⁱ—Co1—N3—C7	171.0 (6)
C3—C4—C5—C6	0.0 (4)	C11—C10—N4—O3	−5.4 (4)
C4—C5—C6—N2	178.2 (2)	C9—C10—N4—O3	175.4 (3)
C4—C5—C6—C1	−0.7 (4)	C11—C10—N4—O4	175.3 (3)
C2—C1—C6—N2	−178.4 (2)	C9—C10—N4—O4	−3.9 (4)
C2—C1—C6—C5	0.7 (4)	C8—C13—N5—C14	157.8 (2)
C13—C8—C9—C10	−0.9 (4)	C12—C13—N5—C14	−23.2 (4)
C8—C9—C10—C11	1.9 (4)	C8—C13—N5—Co1	−42.7 (3)
C8—C9—C10—N4	−178.9 (3)	C12—C13—N5—Co1	136.2 (2)
C9—C10—C11—C12	−1.4 (4)	N6ⁱ—Co1—N5—C14	133.7 (2)
N4—C10—C11—C12	179.4 (3)	O5—Co1—N5—C14	−111.83 (19)
C10—C11—C12—C13	0.0 (4)	N3—Co1—N5—C14	2.21 (19)
C9—C8—C13—C12	−0.5 (4)	N6ⁱ—Co1—N5—C13	−26.2 (2)
C9—C8—C13—N5	178.5 (2)	O5—Co1—N5—C13	88.3 (2)
C11—C12—C13—C8	0.9 (4)	N3—Co1—N5—C13	−157.7 (2)
C11—C12—C13—N5	−178.0 (2)	O5—C15—N7—C16	0.4 (4)
C4—C3—N1—O2	178.9 (3)	O5—C15—N7—C17	−178.6 (3)
C2—C3—N1—O2	−1.0 (5)	N7—C15—O5—Co1	172.1 (2)
C4—C3—N1—O1	−0.1 (4)	N6ⁱ—Co1—O5—C15	−63.6 (3)
C2—C3—N1—O1	−180.0 (3)	N3—Co1—O5—C15	115.0 (2)
C5—C6—N2—C7	13.3 (4)	N5—Co1—O5—C15	−155.2 (2)
C1—C6—N2—C7	−167.7 (2)	N2ⁱ—Co1—O5—C15	23.4 (3)
C5—C6—N2—Co1ⁱⁱ	−141.7 (2)

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

Experimental details

Crystal data
Chemical formula	[Co(C₇H₄N₃O₂)₂(C₃H₇NO)]
M_r	456.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	21.8692 (16), 8.8517 (6), 9.9827 (8)
β (°)	100.151 (6)
V (Å³)	1902.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.95
Crystal size (mm)	0.3 × 0.12 × 0.1

Data collection
Diffractometer	STOE IPDS II diffractometer
Absorption correction	Numerical [optical; X-RED and X-SHAPE (Stoe & Cie, 2005)]
T_min, T_max	0.740, 0.800
No. of measured, independent and observed [I > 2σ(I)] reflections	22258, 5131, 4161
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.689

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.104, 1.20
No. of reflections	5131
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.70

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Co1—O5	1.9807 (19)	Co1—N6ⁱ	1.971 (2)
Co1—N3	1.994 (2)	Co1—N2ⁱ	2.2896 (19)
Co1—N5	2.198 (2)

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

The authors wish to acknowledge Isfahan University of Technology for financial support.

References

Chiniforoshan, H., Jalilpour, S., Shirinfar, B. & Khavasi, H. R. (2009). Acta Cryst. E65, m386. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chisholm, M. H., Hufman, J. C. & Marchant, N. S. (1987). Organometallics, 6, 1073–1080. CSD CrossRef CAS Web of Science Google Scholar
Crutchley, R. J., Desjardins, P. & Yap, G. P. A. (1999). Inorg. Chem. 38, 5901–5905. Google Scholar
Crutchley, R. J. & Naklicki, M. L. (1989). Inorg. Chem. 28, 1955–1958. CrossRef CAS Web of Science Google Scholar
Escuer, A., Mautner, F. A., Sanz, N. & Vicente, R. (2003a). Dalton Trans. pp. 2121–2125. Web of Science CSD CrossRef Google Scholar
Escuer, A., Mautner, F. A., Sanz, N. & Vicente, R. (2003b). Inorg. Chem. 42, 541–551. Web of Science CSD CrossRef PubMed CAS Google Scholar
Escuer, A., Mautner, F. A., Sanz, N. & Vicente, R. (2004). Polyhedron, 23, 1409–1417. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2005). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany. Google Scholar
Storhoff, B. N. & Lewis, H. C. (1977). J. Coord. Chem. Rev. 23, 1–29. CAS Google Scholar

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