metal-organic compounds
trans-Bis[4-amino-N-(pyrimidin-2-yl-κN)benzenesulfonamidato-κN]bis(N,N-dimethylformamide-κO)cobalt(II)
aCollege of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, People's Republic of China
*Correspondence e-mail: zsh720108@163.com
The title complex, [Co(C10H9N4O2S)2(C3H7NO)2], lies across an inversion center. The CoII 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 ). 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).
see: Connor (1998Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2001); cell 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
10.1107/S160053681204336X/wm2693sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681204336X/wm2693Isup2.hkl
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.
H atoms were positioned geometrically and refined with a riding model, with distances 0.86 Å (N—H), 0.96 Å (CH3) or 0.93 Å (aromatic ring), and with Uiso(H) = 1.2 Ueq(aromatic ring, N—H) or Uiso(H) = 1.5 Ueq(CH3). The DMF ligand is positionally disordered over two sets of sites in a 0.559 (4):0.441 (4) ratio.
Data collection: SMART (Bruker, 2001); cell
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).[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) |
[Co(C10H9N4O2S)2(C3H7NO)2] | V = 1614.67 (16) Å3 |
Mr = 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)° |
Bruker SMART CCD diffractometer | 3495 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2989 reflections with I > 2σ(I) |
Tmin = 0.815, Tmax = 0.869 | Rint = 0.028 |
13220 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 36 restraints |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.33 e Å−3 |
3495 reflections | Δρmin = −0.35 e Å−3 |
222 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. |
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 |
Symmetry code: (i) −x, −y+1, −z. |
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] |
Mr | 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) |
Tmin, Tmax | 0.815, 0.869 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13220, 3495, 2989 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.33, −0.35 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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 CoII 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).