trans-Bis[4-amino-N-(pyrimidin-2-yl-κN)benzene­sulfonamidato-κN]bis(N,N-dimethyl­formamide-κO)cobalt(II)

Guo, J.J.; Wang, W.; Zhang, Y.D.; Yang, L.; Zhang, S.H.

doi:10.1107/S160053681204336X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages m1398-m1399

doi:10.1107/S160053681204336X

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trans-Bis[4-amino-N-(pyrimidin-2-yl-κN)benzenesulfonamidato-κN]bis(N,N-dimethylformamide-κO)cobalt(II)

Jing Jing Guo,^a Wei Wang,^a Yi Dong Zhang,^a Li Yang ^a and Shu Hua Zhang ^a ^*

^aCollege of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, People's Republic of China
^*Correspondence e-mail: zsh720108@163.com

(Received 14 October 2012; accepted 18 October 2012; online 24 October 2012)

The title complex, [Co(C₁₀H₉N₄O₂S)₂(C₃H₇NO)₂], lies across an inversion center. The Co^II atom is coordinated in a slightly distorted octahedral geometry by four N atoms from two bidentate 4-amino-N-(pyrimidin-2-yl)benzenesulfonamidate (sulfadiazine) anions and two O atoms from two dimethylformamide (DMF) ligands. The dihedral angle between the benzene and pyrimidine rings is 82.37 (13)°. A three-dimensional network is generated by N—H⋯O hydrogen bonds between the amino groups and of the sulfonamidate O atoms of neighbouring molecules. The DMF ligand is disordered over two sets of sites in a 0.559 (4):0.441 (4) ratio.

Related literature

For background to sulfonamides, see: Connor (1998 ). For background to metal complexes of sulfadiazine, see: Wang et al. (2009 , 2010 ); Ajibade et al. (2006 ); Hossain et al. (2011 ); Tommasino et al. (2011 ); Ghosh et al. (2011 ).

Experimental

Crystal data

[Co(C₁₀H₉N₄O₂S)₂(C₃H₇NO)₂]
M_r = 703.67
Monoclinic, P 2₁ /c
a = 8.9008 (6) Å
b = 11.2078 (6) Å
c = 16.5565 (9) Å
β = 102.147 (6)°
V = 1614.67 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 298 K
0.28 × 0.25 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.815, T_max = 0.869
13220 measured reflections
3495 independent reflections
2989 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.095
S = 0.99
3495 reflections
222 parameters
36 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O1	2.065 (19)
Co1—N1	2.121 (2)
Co1—N2	2.1460 (18)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯O3ⁱ	0.86	2.31	3.112 (3)	155
N4—H4C⋯O3ⁱⁱ	0.86	2.27	2.951 (3)	136
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681204336X/wm2693sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204336X/wm2693Isup2.hkl

checkCIF report

Comment top

Sulfonamides are among the most widely used antibacterial agents (Connor, 1998), because of their low cost, low toxicity, and excellent activity against bacterial diseases. Sulfadiazine, or 4-amino-N-pyrimidin-2-yl-benzenesulfonamide, is a sulfanilamide antibiotic and its metal complexes have been studied previously (Wang et al. 2009, 2010; Ajibade et al., 2006; Hossain et al., 2011; Tommasino et al., 2011; Ghosh et al., 2011). The crystal structure of the title compound, [Co(C₁₀H₉N₄O₂S)₂(C₃H₇NO)₂], a cobalt sulfadiazine complex with additional dimethylformamide ligands, (I), is presented herein.

The molecular structure of (I) is shown in Fig. 1. The Co^II ion lies on a centre of inversion and is coordinated by four N atoms from two symmetry-related 4-amino-N-pyrimidin-2-yl-benzenesulfonamidate anions and two O atoms from two dimethylformamide ligands, forming a slightly distorted octahedral N₄O₂ geometry (Table 1). The dihedral angle between the phenyl and pyrimidine rings is 82.37 (13) °. A three-dimensional hydrogen-bonded network is generated by N—H···O interactions (Table 2; Fig.2).

Related literature top

For background to sulfonamides, see: Connor (1998). For background to metal complexes of sulfadiazine, see: Wang et al. (2009, 2010); Ajibade et al. (2006); Hossain et al. (2011); Tommasino et al. (2011); Ghosh et al. (2011).

Experimental top

Complex (I) was prepared from a mixture of sulfadiazine (1 mmol, 0.250 g), Co(NO₃)₂^.6H₂O (0.5 mmol, 0.145 g), triethylamine (0.5 ml) and N,N-dimethylformamid (8 ml) sealed in a 15 ml teflon-lined stainless steel bomb, and kept at 373 K for 96 h under autogenous pressure. After the reaction was slowly cooled to room temperature, red block-like crystals were obtained (yield: 72% based on cobalt). Anal./calc. for C₂₆H₃₂N₁₀CoO₆S₂(%): C 44.38; H 4.58; N 19.90. Found(%): C 44.34; H 4.61; N 19.95.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. [Symmetry code (a); -x, 1 - y, -z.] Both parts of the disordered DMF ligand are shown.
	Fig. 2. Packing diagram of (I) viewed down [010]. Dashed lines denote N—H···O hydrogen bonds.

trans-Bis[4-amino-N-(pyrimidin-2-yl- κN)benzenesulfonamidato-κN]bis(N,N- dimethylformamide-κO)cobalt(II) top

Crystal data top

[Co(C₁₀H₉N₄O₂S)₂(C₃H₇NO)₂]	F(000) = 730
M_r = 703.67	D_x = 1.447 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4388 reflections
a = 8.9008 (6) Å	θ = 3.0–28.7°
b = 11.2078 (6) Å	µ = 0.72 mm⁻¹
c = 16.5565 (9) Å	T = 298 K
β = 102.147 (6)°	Block, red
V = 1614.67 (16) Å³	0.28 × 0.25 × 0.20 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	3495 independent reflections
Radiation source: fine-focus sealed tube	2989 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 0 pixels mm^-1	θ_max = 27.0°, θ_min = 3.0°
phi and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −14→13
T_min = 0.815, T_max = 0.869	l = −21→19
13220 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0311P)² + 1.5416P] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
3495 reflections	Δρ_max = 0.33 e Å⁻³
222 parameters	Δρ_min = −0.35 e Å⁻³
36 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0012 (1)

Crystal data top

[Co(C₁₀H₉N₄O₂S)₂(C₃H₇NO)₂]	V = 1614.67 (16) Å³
M_r = 703.67	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.9008 (6) Å	µ = 0.72 mm⁻¹
b = 11.2078 (6) Å	T = 298 K
c = 16.5565 (9) Å	0.28 × 0.25 × 0.20 mm
β = 102.147 (6)°

Data collection top

Bruker SMART CCD diffractometer	3495 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2989 reflections with I > 2σ(I)
T_min = 0.815, T_max = 0.869	R_int = 0.028
13220 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	36 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 0.99	Δρ_max = 0.33 e Å⁻³
3495 reflections	Δρ_min = −0.35 e Å⁻³
222 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.

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	Occ. (<1)
C1	0.4095 (3)	0.9002 (2)	0.13724 (16)	0.0476 (6)
H1A	0.4447	0.9344	0.0935	0.057*
C2	0.3251 (2)	0.7957 (2)	0.12498 (14)	0.0363 (5)
C3	0.2761 (3)	0.7454 (3)	0.19139 (15)	0.0507 (6)
H3A	0.2212	0.6742	0.1843	0.061*
C4	0.3079 (3)	0.7994 (3)	0.26800 (16)	0.0572 (7)
H4A	0.2744	0.7640	0.3119	0.069*
C5	0.3892 (3)	0.9061 (3)	0.28047 (16)	0.0508 (7)
C6	0.4421 (3)	0.9543 (3)	0.21390 (17)	0.0568 (7)
H6A	0.5002	1.0240	0.2213	0.068*
C7	−0.0153 (2)	0.73277 (19)	0.00525 (13)	0.0319 (5)
C8	−0.1683 (3)	0.8945 (2)	−0.00174 (16)	0.0438 (6)
H8A	−0.1808	0.9767	0.0005	0.053*
C9	−0.2982 (3)	0.8242 (2)	−0.01745 (18)	0.0513 (7)
H9A	−0.3961	0.8573	−0.0260	0.062*
C10	−0.2766 (3)	0.7031 (2)	−0.01992 (17)	0.0497 (6)
H10A	−0.3616	0.6528	−0.0293	0.060*
Co1	0.0000	0.5000	0.0000	0.03466 (14)
N1	−0.1368 (2)	0.65637 (17)	−0.00916 (13)	0.0402 (5)
N2	0.1174 (2)	0.66834 (16)	0.01562 (12)	0.0350 (4)
N3	−0.0252 (2)	0.85105 (17)	0.01044 (12)	0.0372 (4)
N4	0.4124 (3)	0.9634 (3)	0.35511 (15)	0.0724 (8)
H4B	0.3765	0.9335	0.3950	0.087*
H4C	0.4629	1.0294	0.3621	0.087*
O2	0.29575 (19)	0.81638 (15)	−0.03312 (10)	0.0437 (4)
O3	0.38724 (19)	0.62601 (16)	0.02969 (12)	0.0519 (5)
S1	0.28414 (6)	0.72636 (5)	0.02742 (3)	0.03470 (15)
O1	0.0274 (19)	0.4809 (16)	0.1263 (12)	0.053 (2)	0.559 (4)
C11	−0.0332 (9)	0.5365 (7)	0.1739 (6)	0.0563 (17)	0.559 (4)
H11A	−0.1225	0.5630	0.1388	0.084*	0.559 (4)
C13	−0.1386 (10)	0.6711 (8)	0.2810 (5)	0.107 (2)	0.559 (4)
H13A	−0.1134	0.6764	0.3402	0.160*	0.559 (4)
H13B	−0.1218	0.7471	0.2577	0.160*	0.559 (4)
H13C	−0.2446	0.6489	0.2632	0.160*	0.559 (4)
C12	0.0603 (12)	0.5055 (8)	0.3034 (5)	0.098 (2)	0.559 (4)
H12A	0.1286	0.4397	0.3204	0.147*	0.559 (4)
H12B	0.1008	0.5758	0.3334	0.147*	0.559 (4)
H12C	−0.0388	0.4876	0.3145	0.147*	0.559 (4)
N5	−0.0499 (7)	0.5829 (5)	0.2463 (3)	0.0665 (13)	0.559 (4)
O1'	−0.009 (3)	0.501 (2)	0.1318 (16)	0.053 (2)	0.441 (4)
C11'	−0.0812 (12)	0.5748 (10)	0.1647 (7)	0.0563 (17)	0.441 (4)
H11B	−0.1748	0.6128	0.1375	0.084*	0.441 (4)
C13'	0.1448 (14)	0.4546 (11)	0.2886 (6)	0.107 (2)	0.441 (4)
H13D	0.1783	0.4035	0.2493	0.160*	0.441 (4)
H13E	0.2274	0.5065	0.3134	0.160*	0.441 (4)
H13F	0.1146	0.4068	0.3306	0.160*	0.441 (4)
C12'	−0.0588 (13)	0.5888 (10)	0.3139 (5)	0.098 (2)	0.441 (4)
H12D	−0.0379	0.5933	0.3731	0.147*	0.441 (4)
H12E	−0.0382	0.6648	0.2916	0.147*	0.441 (4)
H12F	−0.1647	0.5681	0.2937	0.147*	0.441 (4)
N5'	0.0174 (10)	0.5244 (7)	0.2573 (5)	0.0665 (13)	0.441 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0493 (14)	0.0501 (15)	0.0422 (13)	−0.0135 (12)	0.0066 (11)	0.0020 (12)
C2	0.0331 (11)	0.0383 (12)	0.0342 (11)	−0.0024 (9)	−0.0004 (9)	0.0011 (10)
C3	0.0565 (15)	0.0515 (16)	0.0409 (13)	−0.0211 (13)	0.0031 (11)	0.0010 (12)
C4	0.0653 (17)	0.0698 (19)	0.0340 (13)	−0.0220 (15)	0.0047 (12)	0.0016 (13)
C5	0.0473 (14)	0.0605 (17)	0.0386 (13)	−0.0069 (12)	−0.0049 (11)	−0.0041 (12)
C6	0.0605 (17)	0.0523 (16)	0.0527 (16)	−0.0222 (14)	0.0006 (13)	−0.0068 (13)
C7	0.0351 (11)	0.0280 (11)	0.0313 (11)	−0.0031 (9)	0.0038 (9)	−0.0032 (9)
C8	0.0448 (13)	0.0333 (12)	0.0533 (15)	0.0049 (10)	0.0103 (11)	−0.0007 (11)
C9	0.0366 (12)	0.0485 (15)	0.0697 (18)	0.0047 (11)	0.0130 (12)	0.0027 (13)
C10	0.0359 (13)	0.0469 (15)	0.0657 (17)	−0.0097 (11)	0.0095 (12)	−0.0025 (13)
Co1	0.0448 (3)	0.0246 (2)	0.0328 (2)	−0.00372 (17)	0.00405 (18)	−0.00398 (17)
N1	0.0384 (10)	0.0322 (10)	0.0489 (12)	−0.0077 (8)	0.0066 (9)	−0.0043 (9)
N2	0.0353 (9)	0.0254 (9)	0.0416 (10)	−0.0006 (7)	0.0021 (8)	−0.0041 (8)
N3	0.0375 (10)	0.0269 (9)	0.0457 (11)	−0.0010 (8)	0.0056 (8)	−0.0031 (8)
N4	0.0836 (18)	0.0854 (19)	0.0428 (13)	−0.0255 (16)	0.0012 (13)	−0.0148 (13)
O2	0.0474 (9)	0.0473 (10)	0.0369 (9)	−0.0027 (8)	0.0099 (7)	0.0049 (8)
O3	0.0441 (9)	0.0492 (11)	0.0617 (11)	0.0162 (8)	0.0092 (8)	−0.0004 (9)
S1	0.0324 (3)	0.0339 (3)	0.0365 (3)	0.0030 (2)	0.0044 (2)	0.0001 (2)
O1	0.078 (7)	0.052 (5)	0.033 (2)	−0.005 (4)	0.020 (4)	−0.008 (3)
C11	0.062 (4)	0.067 (4)	0.041 (2)	−0.019 (3)	0.014 (3)	−0.008 (3)
C13	0.140 (5)	0.126 (5)	0.068 (3)	0.001 (4)	0.051 (3)	0.000 (3)
C12	0.128 (5)	0.118 (5)	0.049 (3)	−0.017 (4)	0.020 (3)	−0.012 (3)
N5	0.089 (3)	0.070 (3)	0.0436 (18)	−0.019 (2)	0.021 (2)	−0.007 (2)
O1'	0.078 (7)	0.052 (5)	0.033 (2)	−0.005 (4)	0.020 (4)	−0.008 (3)
C11'	0.062 (4)	0.067 (4)	0.041 (2)	−0.019 (3)	0.014 (3)	−0.008 (3)
C13'	0.140 (5)	0.126 (5)	0.068 (3)	0.001 (4)	0.051 (3)	0.000 (3)
C12'	0.128 (5)	0.118 (5)	0.049 (3)	−0.017 (4)	0.020 (3)	−0.012 (3)
N5'	0.089 (3)	0.070 (3)	0.0436 (18)	−0.019 (2)	0.021 (2)	−0.007 (2)

Geometric parameters (Å, º) top

C1—C6	1.381 (4)	Co1—O1'	2.20 (2)
C1—C2	1.383 (3)	N2—S1	1.5941 (18)
C1—H1A	0.9300	N4—H4B	0.8600
C2—C3	1.385 (3)	N4—H4C	0.8600
C2—S1	1.760 (2)	O2—S1	1.4412 (17)
C3—C4	1.380 (4)	O3—S1	1.4470 (17)
C3—H3A	0.9300	O1—C11	1.216 (13)
C4—C5	1.390 (4)	C11—N5	1.342 (10)
C4—H4A	0.9300	C11—H11A	0.9300
C5—N4	1.370 (3)	C13—N5	1.457 (9)
C5—C6	1.396 (4)	C13—H13A	0.9602
C6—H6A	0.9300	C13—H13B	0.9597
C7—N3	1.333 (3)	C13—H13C	0.9600
C7—N1	1.360 (3)	C13—H12E	0.8765
C7—N2	1.364 (3)	C12—N5	1.489 (11)
C8—N3	1.339 (3)	C12—H12A	0.9599
C8—C9	1.378 (3)	C12—H12B	0.9600
C8—H8A	0.9300	C12—H12C	0.9601
C9—C10	1.373 (4)	O1'—C11'	1.244 (17)
C9—H9A	0.9300	C11'—N5'	1.694 (14)
C10—N1	1.327 (3)	C11'—H11B	0.9593
C10—H10A	0.9300	C13'—N5'	1.386 (13)
Co1—O1ⁱ	2.065 (19)	C13'—H13D	0.9600
Co1—O1	2.065 (19)	C13'—H13E	0.9600
Co1—N1	2.121 (2)	C13'—H13F	0.9600
Co1—N1ⁱ	2.121 (2)	C12'—N5'	1.458 (13)
Co1—N2	2.1460 (18)	C12'—H12D	0.9597
Co1—N2ⁱ	2.1460 (18)	C12'—H12E	0.9601
Co1—O1'ⁱ	2.20 (2)	C12'—H12F	0.9601

C6—C1—C2	120.6 (2)	N5—C13—H13B	107.4
C6—C1—H1A	119.7	H13A—C13—H13B	109.5
C2—C1—H1A	119.7	N5—C13—H13C	106.4
C1—C2—C3	118.7 (2)	H13A—C13—H13C	109.4
C1—C2—S1	120.66 (19)	H13B—C13—H13C	109.5
C3—C2—S1	120.62 (18)	N5—C13—H12E	53.8
C4—C3—C2	120.9 (2)	H13A—C13—H12E	77.9
C4—C3—H3A	119.6	H13B—C13—H12E	85.1
C2—C3—H3A	119.6	H13C—C13—H12E	159.2
C3—C4—C5	120.9 (3)	N5—C13—H12F	63.8
C3—C4—H4A	119.6	H13A—C13—H12F	83.9
C5—C4—H4A	119.6	H13B—C13—H12F	166.5
N4—C5—C4	120.8 (3)	H13C—C13—H12F	65.9
N4—C5—C6	121.2 (3)	H12E—C13—H12F	96.5
C4—C5—C6	117.9 (2)	N5—C12—H12A	157.8
C1—C6—C5	121.0 (2)	N5—C12—H12B	88.6
C1—C6—H6A	119.5	H12A—C12—H12B	109.5
C5—C6—H6A	119.5	N5—C12—H12C	74.6
N3—C7—N1	125.2 (2)	H12A—C12—H12C	109.5
N3—C7—N2	125.86 (19)	H12B—C12—H12C	109.5
N1—C7—N2	108.91 (19)	N5—C12—H13E	125.9
N3—C8—C9	123.7 (2)	H12A—C12—H13E	53.6
N3—C8—H8A	118.2	H12B—C12—H13E	70.9
C9—C8—H8A	118.2	H12C—C12—H13E	159.1
C10—C9—C8	117.0 (2)	N5—C12—H13F	153.6
C10—C9—H9A	121.5	H12B—C12—H13F	117.7
C8—C9—H9A	121.5	H12C—C12—H13F	92.7
N1—C10—C9	121.3 (2)	H13E—C12—H13F	70.1
N1—C10—H10A	119.3	C11—N5—C13	141.8 (7)
C9—C10—H10A	119.3	C11—N5—C12	99.2 (6)
O1ⁱ—Co1—O1	180.0 (10)	C13—N5—C12	119.0 (6)
O1ⁱ—Co1—N1	84.2 (3)	C11—N5—H12E	149.4
O1—Co1—N1	95.8 (3)	C12—N5—H12E	95.2
O1ⁱ—Co1—N1ⁱ	95.8 (3)	C11—N5—H12F	132.3
O1—Co1—N1ⁱ	84.2 (3)	C13—N5—H12F	49.4
N1—Co1—N1ⁱ	180.00 (11)	C12—N5—H12F	92.0
O1ⁱ—Co1—N2	89.0 (6)	H12E—N5—H12F	73.5
O1—Co1—N2	91.0 (6)	C11'—O1'—Co1	124.5 (17)
N1—Co1—N2	62.59 (7)	O1'—C11'—N5'	87.5 (14)
N1ⁱ—Co1—N2	117.41 (7)	O1'—C11'—H11B	124.6
O1ⁱ—Co1—N2ⁱ	91.0 (6)	N5'—C11'—H11B	143.7
O1—Co1—N2ⁱ	89.0 (6)	N5'—C13'—H12A	99.0
N1—Co1—N2ⁱ	117.41 (7)	N5'—C13'—H13D	115.4
N1ⁱ—Co1—N2ⁱ	62.59 (7)	H12A—C13'—H13D	126.7
N2—Co1—N2ⁱ	180.0	N5'—C13'—H13E	108.1
O1ⁱ—Co1—O1'ⁱ	10.6 (8)	H12A—C13'—H13E	95.5
O1—Co1—O1'ⁱ	169.4 (8)	H13D—C13'—H13E	109.5
N1—Co1—O1'ⁱ	94.1 (5)	N5'—C13'—H13F	104.7
N1ⁱ—Co1—O1'ⁱ	85.9 (5)	H13D—C13'—H13F	109.5
N2—Co1—O1'ⁱ	90.2 (7)	H13E—C13'—H13F	109.5
N2ⁱ—Co1—O1'ⁱ	89.8 (7)	N5'—C12'—H13A	154.8
O1ⁱ—Co1—O1'	169.4 (8)	N5'—C12'—H12B	60.6
O1—Co1—O1'	10.6 (8)	H13A—C12'—H12B	117.7
N1—Co1—O1'	85.9 (5)	N5'—C12'—H12C	54.9
N1ⁱ—Co1—O1'	94.1 (5)	H13A—C12'—H12C	150.1
N2—Co1—O1'	89.8 (7)	H12B—C12'—H12C	75.3
N2ⁱ—Co1—O1'	90.2 (7)	N5'—C12'—H12D	131.7
O1'ⁱ—Co1—O1'	180.000 (3)	H13A—C12'—H12D	66.3
C10—N1—C7	117.6 (2)	H12B—C12'—H12D	78.5
C10—N1—Co1	147.50 (17)	H12C—C12'—H12D	92.6
C7—N1—Co1	94.85 (14)	N5'—C12'—H12E	92.3
C7—N2—S1	123.96 (15)	H13A—C12'—H12E	62.9
C7—N2—Co1	93.64 (13)	H12B—C12'—H12E	85.1
S1—N2—Co1	142.24 (11)	H12C—C12'—H12E	146.9
C7—N3—C8	115.21 (19)	H12D—C12'—H12E	109.5
C5—N4—H4B	120.0	N5'—C12'—H12F	102.2
C5—N4—H4C	120.0	H13A—C12'—H12F	83.3
H4B—N4—H4C	120.0	H12B—C12'—H12F	158.7
O2—S1—O3	115.11 (11)	H12C—C12'—H12F	84.4
O2—S1—N2	113.67 (10)	H12D—C12'—H12F	109.5
O3—S1—N2	104.78 (10)	H12E—C12'—H12F	109.5
O2—S1—C2	107.31 (11)	C13'—N5'—C12'	119.6 (8)
O3—S1—C2	108.17 (11)	C13'—N5'—C11'	138.9 (8)
N2—S1—C2	107.48 (10)	C12'—N5'—C11'	101.2 (8)
C11—O1—Co1	129.0 (12)	C13'—N5'—H12B	70.6
O1—C11—N5	157.5 (12)	C12'—N5'—H12B	57.6
O1—C11—H11A	101.2	C11'—N5'—H12B	137.0
N5—C11—H11A	101.2	C13'—N5'—H12C	87.5
O1—C11—H11B	118.0	C12'—N5'—H12C	49.6
N5—C11—H11B	84.2	C11'—N5'—H12C	126.1
N5—C13—H13A	114.5	H12B—N5'—H12C	71.3

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
N4—H4B···O3ⁱⁱ	0.86	2.31	3.112 (3)	155
N4—H4C···O3ⁱⁱⁱ	0.86	2.27	2.951 (3)	136

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₀H₉N₄O₂S)₂(C₃H₇NO)₂]
M_r	703.67
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.9008 (6), 11.2078 (6), 16.5565 (9)
β (°)	102.147 (6)
V (Å³)	1614.67 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.28 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.815, 0.869
No. of measured, independent and observed [I > 2σ(I)] reflections	13220, 3495, 2989
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.095, 0.99
No. of reflections	3495
No. of parameters	222
No. of restraints	36
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.35

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—O1	2.065 (19)	Co1—N2	2.1460 (18)
Co1—N1	2.121 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O3ⁱ	0.86	2.31	3.112 (3)	155.1
N4—H4C···O3ⁱⁱ	0.86	2.27	2.951 (3)	136.0

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

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (No. 21161006), the Innovation Project of Guangxi Graduate Education (2010105960817M03) and by the doctoral start-up research fund of Guilin University of Technology (to SHZ).

References

Ajibade, P. A., Kolawole, G. A., O'Brien, P., Helliwell, M. & Raftery, J. (2006). Inorg. Chim. Acta, 359, 3111–3116. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Connor, E. E. (1998). Prim. Care Update Ob Gyns, 5, 32–35. CrossRef Google Scholar
Ghosh, S., Bag, P. P. & Reddy, C. M. (2011). Cryst. Growth Des. 11, 3489–3503. Web of Science CSD CrossRef CAS Google Scholar
Hossain, G. M. G. (2011). Acta Cryst. E67, m805–m806. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tommasino, J. B., Renaud, F. N. R., Luneau, D. & Pilet, G. (2011). Polyhedron, 30, 1663–1670. Web of Science CSD CrossRef CAS Google Scholar
Wang, Y.-F., Li, F.-X., Peng, Y., Chen, Z.-F. & Liang, H. (2009). Acta Cryst. E65, m1584. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, Y.-F., Zou, H.-L., Luo, X.-J., Chen, Z.-F. & Liang, H. (2010). Acta Cryst. E66, m548. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 11| November 2012| Pages m1398-m1399

doi:10.1107/S160053681204336X

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

trans-Bis[4-amino-N-(pyrimidin-2-yl-κN)benzene­sulfonamidato-κN]bis­(N,N-di­methyl­formamide-κO)cobalt(II)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

trans-Bis[4-amino-N-(pyrimidin-2-yl-κN)benzenesulfonamidato-κN]bis(N,N-dimethylformamide-κO)cobalt(II)