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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4,6-Dimeth­­oxy-2-(methyl­sulfon­yl)pyrimidine

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Chemistry, Manipal Institute of Technology, Manipal University, Manipal 576 104, India, cOrganic Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and dDepartment of Printing, Manipal Institute of Technology, Manipal University, Manipal 576 104, India
*Correspondence e-mail: hkfun@usm.my

(Received 25 June 2010; accepted 25 June 2010; online 3 July 2010)

The asymmetric unit of the title compound, C7H10N2O4S, comprises of two independent mol­ecules (A and B) which differ in the orientation of the methyl­sulfonyl group [C—S—C—N = 157.98 (13)° in mol­ecule A and 6.09 (18)° in mol­ecule B]. In the crystal structure, mol­ecules of type A are linked into chains along the a axis by inter­molecular C—H⋯O hydrogen bonds. The B mol­ecules are linked to these chains by C—H⋯O hydrogen bonds.

Related literature

For general background and applications of 4,6-dimeth­oxy­pyrimidin-2-yl derivatives, see: Xi et al. (2006[Xi, Z., Yu, Z. H., Niu, C. W., Ban, S. R. & Yang, G. F. (2006). J. Comput. Chem. 27, 1572-1576.]); He et al. (2007[He, Y. Z., Li, Y. X., Zhu, X. L., Xi, Z., Niu, C. W., Wan, J., Zhang, L. & Yang, G. F. (2007). J. Chem. Inf. Model. 47, 2335-2344.]); Li et al. (2006[Li, Y. X., Luo, Y. P., Xi, Z., Niu, C. W., He, Y. Z. & Yang, G. F. (2006). J. Agric. Food Chem. 54, 9135-9139.]); Gerorge (1983[Gerorge, L. (1983). US Patent No. 4 394 506.]).

[Scheme 1]

Experimental

Crystal data
  • C7H10N2O4S

  • Mr = 218.23

  • Triclinic, [P \overline 1]

  • a = 8.349 (2) Å

  • b = 11.067 (3) Å

  • c = 11.438 (3) Å

  • α = 108.457 (8)°

  • β = 92.774 (8)°

  • γ = 98.504 (8)°

  • V = 986.4 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.32 mm−1

  • T = 296 K

  • 0.38 × 0.30 × 0.08 mm

Data collection
  • Bruker APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.889, Tmax = 0.974

  • 29277 measured reflections

  • 7063 independent reflections

  • 4866 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.156

  • S = 1.08

  • 7063 reflections

  • 259 parameters

  • H-atom parameters constrained

  • Δρmax = 0.50 e Å−3

  • Δρmin = −0.50 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3A—H3AA⋯O2Ai 0.93 2.42 3.336 (2) 169
C5A—H5AC⋯O2Bii 0.96 2.55 3.303 (3) 135
C7A—H7AA⋯O4Aiii 0.96 2.50 3.426 (2) 161
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Compounds containing 4,6-dimethoxypyrimidin-2-yl moieties display excellent herbicidal activity (Xi et al., 2006). Most sulfonylurea herbicides and all pyrimidinylbenzoate herbicides (He et al., 2007), such as nicofulfuron, amidosulfuron, halopyrazosulfuron, ethoxysulfuron, pyriminobac-methyl and pyriftalid, possess 4,6-dimethoxypyrimidin-2-yl groups (Li et al., 2006), while sulfometuron-methyl, a kind of sulfonylurea, contains a 4,6-dimethylpyrimidin-2-yl group, which suggests that the two disubstituted pyrimidin- 2-yl groups possess high biological activity (Gerorge, 1983).

There are two molecules, A and B, in the asymmetric unit (Fig. 1) of the title compound. The molecules A and B differ in the orientation of the methylsulfonyl group [C7A—S1A—C1A—N1A = 157.98 (13)° and C7B—S1B—C1B—N2B = 6.09 (18)°]

In the crystal structure, the A molecules are linked into chains along a axis by intermolecular C3A—H3AA···O2A and C7A—H7AA···O4A hydrogen bonds. The B molecules are linked to these chains by intermolecular C5A—H5AC···O2B hydrogen bonds.

Related literature top

For general background and applications of 4,6-dimethoxypyrimidin-2-yl derivatives, see: Xi et al. (2006); He et al. (2007); Li et al. (2006); Gerorge (1983).

Experimental top

Periodic acid (2.63 mmol, 600 mg) was dissolved in acetonitrile (6 ml) by stirring at room temperature for 1 h. To this solution, chromium trioxide (0.125 mmol, 12.5 mg) was added and stirred for 5 min to give a clear orange solution. H5IO6/CrO3 solution (1.7 ml) was added to a solution of 4,6-dimethoxy-2-methylmercaptopyrimidine (0.23 mmol) in ethyl acetate and was stirred at room temperature for 30 min. The reaction mixture was quenched with saturated sodium sulphite and was loaded on to a silica column. The column was eluted with acetone to obtain 4,6-dimethoxy-2-methylsulfonylpyrimidine. Single crystals were recrystallized from an dichloromethane solution (yield: 87%, m.p. 402–405 K).

Refinement top

All H atoms were positioned geometrically [C–H = 0.93 or 0.96 Å] and refined using a riding model, with Uiso(H) = 1.2 or 1.5Ueq(C). A rotating-group model was applied for the methyl groups.

Structure description top

Compounds containing 4,6-dimethoxypyrimidin-2-yl moieties display excellent herbicidal activity (Xi et al., 2006). Most sulfonylurea herbicides and all pyrimidinylbenzoate herbicides (He et al., 2007), such as nicofulfuron, amidosulfuron, halopyrazosulfuron, ethoxysulfuron, pyriminobac-methyl and pyriftalid, possess 4,6-dimethoxypyrimidin-2-yl groups (Li et al., 2006), while sulfometuron-methyl, a kind of sulfonylurea, contains a 4,6-dimethylpyrimidin-2-yl group, which suggests that the two disubstituted pyrimidin- 2-yl groups possess high biological activity (Gerorge, 1983).

There are two molecules, A and B, in the asymmetric unit (Fig. 1) of the title compound. The molecules A and B differ in the orientation of the methylsulfonyl group [C7A—S1A—C1A—N1A = 157.98 (13)° and C7B—S1B—C1B—N2B = 6.09 (18)°]

In the crystal structure, the A molecules are linked into chains along a axis by intermolecular C3A—H3AA···O2A and C7A—H7AA···O4A hydrogen bonds. The B molecules are linked to these chains by intermolecular C5A—H5AC···O2B hydrogen bonds.

For general background and applications of 4,6-dimethoxypyrimidin-2-yl derivatives, see: Xi et al. (2006); He et al. (2007); Li et al. (2006); Gerorge (1983).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The two independent molecules of the title compound with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The crystal packing of title compound, viewed down the b axis showing chains along the a axis.
4,6-Dimethoxy-2-(methylsulfonyl)pyrimidine top
Crystal data top
C7H10N2O4SZ = 4
Mr = 218.23F(000) = 456
Triclinic, P1Dx = 1.470 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.349 (2) ÅCell parameters from 8362 reflections
b = 11.067 (3) Åθ = 2.2–32.1°
c = 11.438 (3) ŵ = 0.32 mm1
α = 108.457 (8)°T = 296 K
β = 92.774 (8)°Plate, colourless
γ = 98.504 (8)°0.38 × 0.30 × 0.08 mm
V = 986.4 (4) Å3
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer
7063 independent reflections
Radiation source: fine-focus sealed tube4866 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
φ and ω scansθmax = 32.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1212
Tmin = 0.889, Tmax = 0.974k = 1616
29277 measured reflectionsl = 1716
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0771P)2 + 0.1962P]
where P = (Fo2 + 2Fc2)/3
7063 reflections(Δ/σ)max = 0.001
259 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.50 e Å3
Crystal data top
C7H10N2O4Sγ = 98.504 (8)°
Mr = 218.23V = 986.4 (4) Å3
Triclinic, P1Z = 4
a = 8.349 (2) ÅMo Kα radiation
b = 11.067 (3) ŵ = 0.32 mm1
c = 11.438 (3) ÅT = 296 K
α = 108.457 (8)°0.38 × 0.30 × 0.08 mm
β = 92.774 (8)°
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer
7063 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
4866 reflections with I > 2σ(I)
Tmin = 0.889, Tmax = 0.974Rint = 0.042
29277 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.156H-atom parameters constrained
S = 1.08Δρmax = 0.50 e Å3
7063 reflectionsΔρmin = 0.50 e Å3
259 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
xyzUiso*/Ueq
S1A0.01034 (4)0.04422 (4)0.19330 (4)0.03856 (12)
O1A0.02361 (19)0.10070 (16)0.32304 (15)0.0632 (4)
O2A0.08995 (15)0.09457 (13)0.10934 (15)0.0518 (3)
O3A0.50597 (16)0.29863 (13)0.14202 (15)0.0528 (3)
O4A0.51835 (16)0.11116 (13)0.16945 (16)0.0543 (3)
N1A0.26662 (16)0.17382 (13)0.16027 (13)0.0362 (3)
N2A0.27464 (15)0.03547 (13)0.17789 (13)0.0364 (3)
C1A0.20400 (17)0.06224 (14)0.17287 (14)0.0334 (3)
C2A0.43408 (19)0.01755 (16)0.16718 (16)0.0386 (3)
C3A0.51867 (19)0.09495 (18)0.15559 (17)0.0435 (4)
H3AA0.63040.10680.15020.052*
C4A0.42742 (19)0.18858 (16)0.15246 (15)0.0378 (3)
C5A0.4131 (3)0.3951 (2)0.1326 (3)0.0608 (5)
H5AA0.48380.46530.11940.091*
H5AB0.36350.42680.20780.091*
H5AC0.33000.35770.06420.091*
C6A0.4289 (3)0.2300 (2)0.1768 (3)0.0630 (6)
H6AA0.50320.28720.18140.095*
H6AB0.35250.27040.10450.095*
H6AC0.37140.21160.24940.095*
C7A0.0758 (2)0.12239 (17)0.1485 (2)0.0476 (4)
H7AA0.19090.14000.15360.071*
H7AB0.01970.15710.20240.071*
H7AC0.05290.16180.06480.071*
S1B0.91824 (6)0.54889 (4)0.18573 (4)0.04122 (12)
O1B1.0732 (2)0.63051 (15)0.21079 (16)0.0655 (4)
O2B0.8041 (2)0.56321 (17)0.09628 (13)0.0639 (4)
O3B0.7212 (2)0.42513 (15)0.54172 (14)0.0673 (5)
O4B0.6688 (2)0.83263 (14)0.52687 (15)0.0629 (4)
N1B0.78624 (19)0.69578 (14)0.36974 (14)0.0437 (3)
N2B0.81160 (19)0.48548 (14)0.37722 (13)0.0414 (3)
C1B0.8263 (2)0.57971 (16)0.32927 (15)0.0382 (3)
C2B0.7173 (2)0.71868 (18)0.47615 (17)0.0471 (4)
C3B0.6896 (3)0.6287 (2)0.53590 (18)0.0574 (5)
H3BA0.63830.64540.60840.069*
C4B0.7415 (3)0.51237 (18)0.48331 (17)0.0479 (4)
C5B0.7711 (4)0.3023 (2)0.4853 (2)0.0658 (6)
H5BA0.77100.25640.54380.099*
H5BB0.87870.31630.46070.099*
H5BC0.69670.25250.41380.099*
C6B0.7263 (4)0.9364 (2)0.4804 (2)0.0717 (7)
H6BA0.70751.01680.53700.108*
H6BB0.66890.92100.40090.108*
H6BC0.84080.94060.47250.108*
C7B0.9425 (3)0.38667 (19)0.1441 (2)0.0596 (6)
H7BA0.98600.36200.06550.089*
H7BB0.83890.33320.13840.089*
H7BC1.01600.37580.20580.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.02471 (18)0.03529 (19)0.0583 (3)0.00757 (13)0.01261 (15)0.01667 (17)
O1A0.0498 (8)0.0687 (9)0.0636 (9)0.0117 (7)0.0238 (7)0.0079 (7)
O2A0.0291 (6)0.0482 (7)0.0888 (10)0.0116 (5)0.0074 (6)0.0351 (7)
O3A0.0338 (6)0.0503 (7)0.0794 (10)0.0034 (5)0.0040 (6)0.0332 (7)
O4A0.0313 (6)0.0516 (7)0.0890 (10)0.0153 (5)0.0114 (6)0.0311 (7)
N1A0.0264 (6)0.0368 (6)0.0450 (7)0.0026 (5)0.0036 (5)0.0143 (5)
N2A0.0255 (6)0.0385 (6)0.0472 (7)0.0077 (5)0.0063 (5)0.0156 (6)
C1A0.0226 (6)0.0364 (7)0.0410 (8)0.0041 (5)0.0052 (5)0.0126 (6)
C2A0.0265 (7)0.0440 (8)0.0473 (9)0.0093 (6)0.0055 (6)0.0159 (7)
C3A0.0235 (7)0.0518 (9)0.0575 (10)0.0048 (6)0.0060 (6)0.0216 (8)
C4A0.0283 (7)0.0419 (8)0.0433 (8)0.0003 (6)0.0034 (6)0.0167 (6)
C5A0.0500 (11)0.0536 (11)0.0890 (16)0.0007 (9)0.0077 (10)0.0411 (11)
C6A0.0476 (11)0.0511 (11)0.1001 (18)0.0169 (9)0.0138 (11)0.0339 (11)
C7A0.0319 (8)0.0385 (8)0.0761 (13)0.0027 (6)0.0102 (8)0.0249 (8)
S1B0.0485 (2)0.0379 (2)0.0431 (2)0.01011 (16)0.01501 (17)0.01859 (16)
O1B0.0583 (9)0.0610 (9)0.0768 (10)0.0036 (7)0.0250 (8)0.0258 (8)
O2B0.0830 (12)0.0751 (10)0.0444 (7)0.0300 (9)0.0083 (7)0.0269 (7)
O3B0.1028 (14)0.0552 (8)0.0543 (8)0.0157 (8)0.0304 (8)0.0283 (7)
O4B0.0800 (11)0.0481 (8)0.0605 (9)0.0220 (7)0.0250 (8)0.0102 (7)
N1B0.0480 (8)0.0403 (7)0.0440 (8)0.0111 (6)0.0096 (6)0.0132 (6)
N2B0.0465 (8)0.0401 (7)0.0396 (7)0.0060 (6)0.0089 (6)0.0160 (6)
C1B0.0382 (8)0.0395 (8)0.0376 (8)0.0067 (6)0.0064 (6)0.0134 (6)
C2B0.0506 (10)0.0433 (9)0.0442 (9)0.0100 (7)0.0103 (7)0.0084 (7)
C3B0.0775 (15)0.0518 (11)0.0430 (10)0.0119 (10)0.0243 (9)0.0126 (8)
C4B0.0593 (11)0.0450 (9)0.0394 (9)0.0040 (8)0.0115 (8)0.0151 (7)
C5B0.0955 (19)0.0489 (11)0.0579 (13)0.0094 (11)0.0111 (12)0.0255 (10)
C6B0.104 (2)0.0477 (11)0.0687 (14)0.0285 (12)0.0197 (13)0.0182 (10)
C7B0.0803 (15)0.0423 (10)0.0653 (13)0.0231 (9)0.0347 (11)0.0206 (9)
Geometric parameters (Å, º) top
S1A—O1A1.4334 (16)S1B—O1B1.4234 (16)
S1A—O2A1.4356 (14)S1B—O2B1.4260 (16)
S1A—C7A1.7429 (18)S1B—C7B1.751 (2)
S1A—C1A1.8059 (15)S1B—C1B1.8018 (17)
O3A—C4A1.338 (2)O3B—C4B1.333 (2)
O3A—C5A1.436 (3)O3B—C5B1.441 (3)
O4A—C2A1.342 (2)O4B—C2B1.342 (2)
O4A—C6A1.443 (2)O4B—C6B1.442 (3)
N1A—C1A1.322 (2)N1B—C1B1.320 (2)
N1A—C4A1.339 (2)N1B—C2B1.339 (2)
N2A—C1A1.321 (2)N2B—C1B1.317 (2)
N2A—C2A1.334 (2)N2B—C4B1.340 (2)
C2A—C3A1.386 (2)C2B—C3B1.375 (3)
C3A—C4A1.382 (2)C3B—C4B1.381 (3)
C3A—H3AA0.93C3B—H3BA0.93
C5A—H5AA0.96C5B—H5BA0.96
C5A—H5AB0.96C5B—H5BB0.96
C5A—H5AC0.96C5B—H5BC0.96
C6A—H6AA0.96C6B—H6BA0.96
C6A—H6AB0.96C6B—H6BB0.96
C6A—H6AC0.96C6B—H6BC0.96
C7A—H7AA0.96C7B—H7BA0.96
C7A—H7AB0.96C7B—H7BB0.96
C7A—H7AC0.96C7B—H7BC0.96
O1A—S1A—O2A117.87 (10)O1B—S1B—O2B117.30 (11)
O1A—S1A—C7A109.37 (10)O1B—S1B—C7B110.02 (12)
O2A—S1A—C7A109.13 (9)O2B—S1B—C7B109.13 (12)
O1A—S1A—C1A107.07 (8)O1B—S1B—C1B107.47 (9)
O2A—S1A—C1A108.07 (8)O2B—S1B—C1B107.25 (9)
C7A—S1A—C1A104.49 (8)C7B—S1B—C1B104.92 (9)
C4A—O3A—C5A118.66 (14)C4B—O3B—C5B118.20 (16)
C2A—O4A—C6A117.66 (14)C2B—O4B—C6B117.81 (17)
C1A—N1A—C4A113.74 (14)C1B—N1B—C2B113.47 (15)
C1A—N2A—C2A113.88 (14)C1B—N2B—C4B113.85 (15)
N2A—C1A—N1A130.25 (14)N2B—C1B—N1B130.63 (16)
N2A—C1A—S1A115.13 (11)N2B—C1B—S1B115.98 (12)
N1A—C1A—S1A114.55 (11)N1B—C1B—S1B113.38 (13)
N2A—C2A—O4A119.16 (15)N1B—C2B—O4B119.64 (18)
N2A—C2A—C3A123.00 (15)N1B—C2B—C3B122.83 (17)
O4A—C2A—C3A117.83 (15)O4B—C2B—C3B117.51 (17)
C4A—C3A—C2A116.11 (15)C2B—C3B—C4B116.88 (17)
C4A—C3A—H3AA121.9C2B—C3B—H3BA121.6
C2A—C3A—H3AA121.9C4B—C3B—H3BA121.6
O3A—C4A—N1A119.54 (15)O3B—C4B—N2B119.62 (17)
O3A—C4A—C3A117.47 (15)O3B—C4B—C3B118.09 (17)
N1A—C4A—C3A122.99 (15)N2B—C4B—C3B122.29 (17)
O3A—C5A—H5AA109.5O3B—C5B—H5BA109.5
O3A—C5A—H5AB109.5O3B—C5B—H5BB109.5
H5AA—C5A—H5AB109.5H5BA—C5B—H5BB109.5
O3A—C5A—H5AC109.5O3B—C5B—H5BC109.5
H5AA—C5A—H5AC109.5H5BA—C5B—H5BC109.5
H5AB—C5A—H5AC109.5H5BB—C5B—H5BC109.5
O4A—C6A—H6AA109.5O4B—C6B—H6BA109.5
O4A—C6A—H6AB109.5O4B—C6B—H6BB109.5
H6AA—C6A—H6AB109.5H6BA—C6B—H6BB109.5
O4A—C6A—H6AC109.5O4B—C6B—H6BC109.5
H6AA—C6A—H6AC109.5H6BA—C6B—H6BC109.5
H6AB—C6A—H6AC109.5H6BB—C6B—H6BC109.5
S1A—C7A—H7AA109.5S1B—C7B—H7BA109.5
S1A—C7A—H7AB109.5S1B—C7B—H7BB109.5
H7AA—C7A—H7AB109.5H7BA—C7B—H7BB109.5
S1A—C7A—H7AC109.5S1B—C7B—H7BC109.5
H7AA—C7A—H7AC109.5H7BA—C7B—H7BC109.5
H7AB—C7A—H7AC109.5H7BB—C7B—H7BC109.5
C2A—N2A—C1A—N1A0.7 (3)C4B—N2B—C1B—N1B1.4 (3)
C2A—N2A—C1A—S1A177.62 (12)C4B—N2B—C1B—S1B179.50 (13)
C4A—N1A—C1A—N2A0.6 (3)C2B—N1B—C1B—N2B1.2 (3)
C4A—N1A—C1A—S1A176.33 (12)C2B—N1B—C1B—S1B179.75 (13)
O1A—S1A—C1A—N2A91.31 (14)O1B—S1B—C1B—N2B110.99 (15)
O2A—S1A—C1A—N2A140.77 (13)O2B—S1B—C1B—N2B122.06 (15)
C7A—S1A—C1A—N2A24.64 (15)C7B—S1B—C1B—N2B6.09 (18)
O1A—S1A—C1A—N1A86.07 (14)O1B—S1B—C1B—N1B68.23 (16)
O2A—S1A—C1A—N1A41.86 (14)O2B—S1B—C1B—N1B58.72 (16)
C7A—S1A—C1A—N1A157.98 (13)C7B—S1B—C1B—N1B174.69 (15)
C1A—N2A—C2A—O4A179.19 (16)C1B—N1B—C2B—O4B179.21 (18)
C1A—N2A—C2A—C3A1.8 (2)C1B—N1B—C2B—C3B0.8 (3)
C6A—O4A—C2A—N2A3.3 (3)C6B—O4B—C2B—N1B14.0 (3)
C6A—O4A—C2A—C3A177.70 (18)C6B—O4B—C2B—C3B167.5 (2)
N2A—C2A—C3A—C4A1.6 (3)N1B—C2B—C3B—C4B2.1 (3)
O4A—C2A—C3A—C4A179.42 (16)O4B—C2B—C3B—C4B179.4 (2)
C5A—O3A—C4A—N1A3.4 (3)C5B—O3B—C4B—N2B2.2 (3)
C5A—O3A—C4A—C3A177.06 (19)C5B—O3B—C4B—C3B178.3 (2)
C1A—N1A—C4A—O3A178.65 (15)C1B—N2B—C4B—O3B179.31 (19)
C1A—N1A—C4A—C3A0.8 (2)C1B—N2B—C4B—C3B0.2 (3)
C2A—C3A—C4A—O3A179.63 (16)C2B—C3B—C4B—O3B177.7 (2)
C2A—C3A—C4A—N1A0.1 (3)C2B—C3B—C4B—N2B1.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3A—H3AA···O2Ai0.932.423.336 (2)169
C5A—H5AC···O2Bii0.962.553.303 (3)135
C7A—H7AA···O4Aiii0.962.503.426 (2)161
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z; (iii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC7H10N2O4S
Mr218.23
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)8.349 (2), 11.067 (3), 11.438 (3)
α, β, γ (°)108.457 (8), 92.774 (8), 98.504 (8)
V3)986.4 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.32
Crystal size (mm)0.38 × 0.30 × 0.08
Data collection
DiffractometerBruker APEXII DUO CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.889, 0.974
No. of measured, independent and
observed [I > 2σ(I)] reflections
29277, 7063, 4866
Rint0.042
(sin θ/λ)max1)0.756
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.156, 1.08
No. of reflections7063
No. of parameters259
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.50, 0.50

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3A—H3AA···O2Ai0.932.423.336 (2)169
C5A—H5AC···O2Bii0.962.553.303 (3)135
C7A—H7AA···O4Aiii0.962.503.426 (2)161
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z; (iii) x1, y, z.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5523-2009.

Acknowledgements

HKF and CSY thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). CSY also thanks USM for the award of a USM Fellowship. AMI is grateful to the Head of the Department of Chemistry and the Director, National Institute of Technology-Karnataka, India, for providing research facilities and for their encouragement. AMI is also thankful to USM for the partial sponsorship of his visit to the X-ray Crystallography Unit, School fo Physics, USM.

References

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First citationHe, Y. Z., Li, Y. X., Zhu, X. L., Xi, Z., Niu, C. W., Wan, J., Zhang, L. & Yang, G. F. (2007). J. Chem. Inf. Model. 47, 2335–2344.  Web of Science CrossRef PubMed CAS Google Scholar
First citationLi, Y. X., Luo, Y. P., Xi, Z., Niu, C. W., He, Y. Z. & Yang, G. F. (2006). J. Agric. Food Chem. 54, 9135–9139.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationXi, Z., Yu, Z. H., Niu, C. W., Ban, S. R. & Yang, G. F. (2006). J. Comput. Chem. 27, 1572–1576.  Web of Science CrossRef Google Scholar

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