trans-Bis[4-amino-N-(pyrimidin-2-yl-κN)benzene-sulfonamidato-κN]bis(N,N-dimethyl-formamide-κO)cobalt(II).

The title complex, [Co(C(10)H(9)N(4)O(2)S)(2)(C(3)H(7)NO)(2)], lies across an inversion center. The Co(II) atom is coordinated in a slightly distorted octa-hedral geometry by four N atoms from two bidentate 4-amino-N-(pyrimidin-2-yl)benzene-sulfonamidate (sulfadiazine) anions and two O atoms from two dimethyl-formamide (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 mol-ecules. 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 = 703.67

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.095

S = 0.99

3495 reflections

222 parameters

36 restraints

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.35 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681204336X/wm2693sup1.cif

Click here for additional data file.

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

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

[Co(C10H9N4O2S)2(C3H7NO)2]	F(000) = 730
Mr = 703.67	Dx = 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

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

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(Fo2) + (0.0311P)2 + 1.5416P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
3495 reflections	Δρmax = 0.33 e Å−3
222 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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

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

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) ; (ii) .