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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

3-Methyl-4-[2-(4-nitro­phen­yl)hydrazin-1-yl­­idene]-5-oxo-4,5-di­hydro-1H-pyrazole-1-carbo­thio­amide

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
*Correspondence e-mail: hkfun@usm.my

(Received 11 June 2012; accepted 15 June 2012; online 23 June 2012)

The asymmetric unit of the title compound, C11H10N6O3S, contains two independent mol­ecules, each of which is stabilized by an intra­molecular N—H⋯O hydrogen bond, forming an S(6) ring motif. In one mol­ecule, the pyrazole ring forms a dihedral angle of 10.93 (14)° with the benzene ring. The corresponding dihedral angle in the other mol­ecule is 7.03 (14)°. In the crystal, mol­ecules are linked via pairs of (N,N)—H⋯O bifurcated acceptor bonds which, together with C—H⋯O hydrogen bonds, form sheets parallel to (001).

Related literature

For general background to and the pharmacological activity of pyrazole derivatives, see: Isloor et al. (2009[Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44, 3784-3787.]); Rai et al. (2008[Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S. & Puranic, V. G. (2008). Eur. J. Med. Chem. 43, 1715-1720.]); Bradbury & Pucci (2008[Bradbury, B. J. & Pucci, M. J. (2008). Curr. Opin. Pharmacol. 8, 574-581.]); Girisha et al. (2010[Girisha, K. S., Kalluraya, B., Narayana, V. & Padmashree (2010). Eur. J. Med. Chem. 45, 4640-4644.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10N6O3S

  • Mr = 306.31

  • Monoclinic, P 21 /c

  • a = 11.5331 (4) Å

  • b = 17.2540 (6) Å

  • c = 13.6025 (5) Å

  • β = 105.840 (2)°

  • V = 2604.01 (16) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 100 K

  • 0.23 × 0.19 × 0.13 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.940, Tmax = 0.965

  • 29927 measured reflections

  • 7706 independent reflections

  • 5153 reflections with I > 2σ(I)

  • Rint = 0.086

Refinement
  • R[F2 > 2σ(F2)] = 0.074

  • wR(F2) = 0.187

  • S = 1.05

  • 7706 reflections

  • 405 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.17 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N5B—H2N5⋯O3B 0.97 (3) 2.08 (3) 2.810 (3) 131 (3)
N1A—H1N1⋯O3Bi 0.88 (4) 2.00 (4) 2.859 (3) 165 (4)
N5A—H1N5⋯O3A 0.92 (3) 2.11 (4) 2.802 (3) 131 (3)
N1B—H3N1⋯O3Aii 0.87 (3) 1.99 (4) 2.848 (3) 171 (3)
C10B—H10B⋯O2Aiii 0.95 2.51 3.418 (3) 161
Symmetry codes: (i) x, y-1, 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

The pyrazole ring is a prominent structural moiety found in numerous pharmaceutically active compounds. This is mainly due to the easy preparation and the important pharmacological activity. Therefore, the synthesis and selective functionalization of pyrazoles have been the focus of active research over the years (Isloor et al., 2009). Pyrazoles have been reported to possess antibacterial activity (Rai et al., 2008), and inhibitor activity against DNA gyrase and topoisomerase IV at their respective ATP-binding sites (Bradbury & Pucci, 2008). Moreover, pyrazole-containing compounds have received considerable attention owing to their diverse chemotherapeutic potentials including versatile anti-inflammatory and antimicrobial activities (Girisha et al., 2010). The synthetic route followed for obtaining the title compound involves the diazotization of substituted anilines to give the diazonium salts followed by coupling with ethyl acetoacetate in the presence of sodium acetate to give the corresponding oxobutanoate which on further reaction with thiosemicarbazide in acetic acid gave the required thioamides.

The asymmetric unit contains two independent molecules (Fig. 1), A and B. Each molecule is stabilized by an intramolecular N–H···O hydrogen bond (Table 1), forming a S(6) ring motif (Bernstein et al., 1995). In molecule A, the pyrazole ring (N2A/N3A/C2A-C4A) forms a dihedral angle of 10.93 (14)° with the benzene ring (C5A-C10A). The corresponding dihedral angle in the molecule B is 7.03 (14)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal (Fig.2), molecules are linked via pairs of intermolecular N5B–H2N5···O3B, N1A–H1N1···O3B and N5A–H1N5···O3A, N1B–H3N1···O3A bifurcated acceptor bonds (Table 1) which together with C10B–H10B···O2A hydrogen bonds form two-dimensional sheets parallel to (001).

Related literature top

For general background to and the pharmacological activity of pyrazole derivatives, see: Isloor et al. (2009); Rai et al. (2008); Bradbury & Pucci (2008); Girisha et al. (2010). For standard bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

To a solution of ethyl-2-[(4-nitrophenyl)hydrazono]-3-oxobutanoate (0.01 mol) dissolved in glacial acetic acid (20 ml), a solution of thiosemicarbazide (0.02 mol) in glacial acetic acid (25 ml) was added and the mixture was refluxed for 4 h. This was cooled and allowed to stand overnight. The solid product which separated out was filtered and dried. It was then recrystallized from ethanol. Crystals suitable for X-ray analysis were obtained by slow evaporation of a solution of the title compound in a 1:2 mixture of DMF and ethanol.

Refinement top

N-bound H atoms were located in a difference Fourier map and refined freely [N–H = 0.84 (4)- 0.98 (4) Å]. The rest of hydrogen atoms were positioned geometrically and refined using a riding model with C–H = 0.95 or 0.98 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating-group model was applied for the methyl groups.

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
Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms. Intramolecular bonds are shown as dashed lines.

Fig. 2. The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.
3-Methyl-4-[2-(4-nitrophenyl)hydrazin-1-ylidene]-5-oxo-4,5-dihydro-1H- pyrazole-1-carbothioamide top
Crystal data top
C11H10N6O3SF(000) = 1264
Mr = 306.31Dx = 1.563 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4616 reflections
a = 11.5331 (4) Åθ = 2.4–29.9°
b = 17.2540 (6) ŵ = 0.27 mm1
c = 13.6025 (5) ÅT = 100 K
β = 105.840 (2)°Block, orange
V = 2604.01 (16) Å30.23 × 0.19 × 0.13 mm
Z = 8
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
7706 independent reflections
Radiation source: fine-focus sealed tube5153 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.086
ϕ and ω scansθmax = 30.2°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1614
Tmin = 0.940, Tmax = 0.965k = 2422
29927 measured reflectionsl = 1919
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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0947P)2 + 0.6575P]
where P = (Fo2 + 2Fc2)/3
7706 reflections(Δ/σ)max = 0.001
405 parametersΔρmax = 1.17 e Å3
0 restraintsΔρmin = 0.45 e Å3
Crystal data top
C11H10N6O3SV = 2604.01 (16) Å3
Mr = 306.31Z = 8
Monoclinic, P21/cMo Kα radiation
a = 11.5331 (4) ŵ = 0.27 mm1
b = 17.2540 (6) ÅT = 100 K
c = 13.6025 (5) Å0.23 × 0.19 × 0.13 mm
β = 105.840 (2)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
7706 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
5153 reflections with I > 2σ(I)
Tmin = 0.940, Tmax = 0.965Rint = 0.086
29927 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0740 restraints
wR(F2) = 0.187H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 1.17 e Å3
7706 reflectionsΔρmin = 0.45 e Å3
405 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > 2sigma(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
S1A0.49627 (7)0.07456 (4)0.34900 (6)0.02459 (18)
O1A1.23941 (18)0.56130 (12)0.40495 (19)0.0319 (5)
O2A1.10770 (18)0.65219 (11)0.39347 (18)0.0290 (5)
O3A0.67596 (17)0.21463 (11)0.36767 (15)0.0218 (4)
N1A0.2988 (2)0.15650 (15)0.3363 (2)0.0228 (5)
N2A0.46510 (19)0.22947 (12)0.34390 (17)0.0167 (4)
N3A0.38600 (19)0.29408 (12)0.33564 (18)0.0183 (5)
N4A0.65953 (19)0.38832 (13)0.35212 (16)0.0171 (4)
N5A0.77001 (19)0.36389 (13)0.36300 (17)0.0172 (4)
N6A1.1355 (2)0.58362 (13)0.39233 (18)0.0193 (5)
C1A0.4155 (2)0.15527 (14)0.3430 (2)0.0182 (5)
C2A0.5845 (2)0.25291 (14)0.35571 (19)0.0154 (5)
C3A0.5750 (2)0.33756 (14)0.35069 (19)0.0157 (5)
C4A0.4505 (2)0.35624 (14)0.3387 (2)0.0176 (5)
C5A0.8602 (2)0.41880 (14)0.36467 (19)0.0163 (5)
C6A0.9803 (2)0.39484 (15)0.3935 (2)0.0179 (5)
H6AA0.99960.34180.40830.021*
C7A1.0711 (2)0.44859 (15)0.4003 (2)0.0182 (5)
H7AA1.15320.43310.41940.022*
C8A1.0399 (2)0.52539 (15)0.37867 (19)0.0165 (5)
C9A0.9203 (2)0.55040 (15)0.3490 (2)0.0182 (5)
H9AA0.90150.60360.33490.022*
C10A0.8299 (2)0.49643 (15)0.3407 (2)0.0182 (5)
H10A0.74780.51180.31890.022*
C11A0.3981 (3)0.43569 (15)0.3332 (2)0.0253 (6)
H11A0.31030.43270.30570.038*
H11B0.43150.46810.28830.038*
H11C0.41810.45840.40170.038*
S1B0.01234 (7)1.16479 (4)0.38971 (6)0.02669 (19)
O1B0.77974 (19)0.69756 (14)0.4551 (2)0.0433 (7)
O2B0.65439 (19)0.60220 (12)0.43636 (18)0.0322 (5)
O3B0.19810 (17)1.02711 (11)0.41542 (15)0.0217 (4)
N1B0.1838 (2)1.07880 (16)0.3673 (2)0.0268 (6)
N2B0.0135 (2)1.00943 (12)0.37488 (17)0.0173 (4)
N3B0.0931 (2)0.94476 (12)0.35002 (17)0.0180 (5)
N4B0.1857 (2)0.85527 (12)0.37418 (16)0.0170 (4)
N5B0.2965 (2)0.88122 (13)0.39365 (18)0.0187 (5)
N6B0.6769 (2)0.67177 (14)0.43667 (19)0.0240 (5)
C1B0.0669 (3)1.08329 (14)0.3765 (2)0.0202 (5)
C2B0.1063 (2)0.98794 (14)0.39107 (19)0.0161 (5)
C3B0.0986 (2)0.90382 (14)0.3735 (2)0.0163 (5)
C4B0.0271 (2)0.88367 (14)0.3494 (2)0.0164 (5)
C5B0.3899 (2)0.82832 (15)0.39719 (19)0.0166 (5)
C6B0.5065 (2)0.85661 (15)0.4119 (2)0.0198 (5)
H6BA0.52070.91090.41510.024*
C7B0.6014 (2)0.80571 (16)0.4220 (2)0.0204 (5)
H7BA0.68140.82420.43190.024*
C8B0.5766 (2)0.72671 (15)0.4171 (2)0.0195 (5)
C9B0.4603 (2)0.69750 (15)0.3996 (2)0.0206 (5)
H9BA0.44620.64320.39470.025*
C10B0.3651 (2)0.74874 (14)0.3893 (2)0.0184 (5)
H10B0.28490.73030.37720.022*
C11B0.0786 (2)0.80485 (15)0.3263 (2)0.0227 (6)
H11D0.16660.80830.30170.034*
H11E0.05610.77310.38840.034*
H11F0.04700.78100.27350.034*
H2N10.263 (3)0.200 (2)0.335 (3)0.044 (11)*
H2N50.313 (3)0.936 (2)0.407 (2)0.032 (9)*
H1N10.261 (3)0.115 (2)0.349 (3)0.042 (11)*
H4N10.215 (4)1.035 (3)0.359 (3)0.049 (12)*
H1N50.788 (3)0.312 (2)0.370 (3)0.033 (9)*
H3N10.223 (3)1.122 (2)0.362 (3)0.038 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0290 (4)0.0084 (3)0.0381 (4)0.0001 (3)0.0121 (3)0.0029 (3)
O1A0.0179 (10)0.0187 (11)0.0617 (15)0.0028 (8)0.0156 (10)0.0040 (10)
O2A0.0235 (10)0.0090 (9)0.0543 (14)0.0009 (8)0.0102 (10)0.0037 (8)
O3A0.0193 (9)0.0125 (9)0.0339 (11)0.0033 (7)0.0080 (8)0.0001 (7)
N1A0.0193 (12)0.0125 (11)0.0360 (14)0.0033 (9)0.0063 (10)0.0034 (10)
N2A0.0182 (10)0.0062 (9)0.0275 (12)0.0016 (8)0.0091 (9)0.0004 (8)
N3A0.0162 (10)0.0107 (10)0.0285 (12)0.0029 (8)0.0069 (9)0.0023 (8)
N4A0.0166 (10)0.0135 (10)0.0218 (11)0.0006 (8)0.0061 (8)0.0002 (8)
N5A0.0146 (10)0.0117 (10)0.0259 (12)0.0006 (8)0.0063 (9)0.0000 (8)
N6A0.0181 (11)0.0132 (10)0.0281 (12)0.0011 (8)0.0089 (9)0.0009 (8)
C1A0.0228 (13)0.0106 (11)0.0207 (13)0.0027 (10)0.0050 (10)0.0018 (9)
C2A0.0168 (12)0.0111 (11)0.0203 (12)0.0003 (9)0.0081 (9)0.0003 (9)
C3A0.0170 (12)0.0106 (11)0.0204 (12)0.0004 (9)0.0068 (9)0.0009 (9)
C4A0.0186 (12)0.0114 (12)0.0244 (13)0.0001 (9)0.0088 (10)0.0009 (9)
C5A0.0179 (12)0.0126 (12)0.0203 (13)0.0018 (9)0.0083 (10)0.0014 (9)
C6A0.0187 (12)0.0127 (12)0.0224 (13)0.0014 (10)0.0060 (10)0.0014 (9)
C7A0.0147 (12)0.0146 (12)0.0259 (14)0.0022 (9)0.0065 (10)0.0006 (10)
C8A0.0166 (12)0.0130 (12)0.0211 (13)0.0029 (9)0.0074 (10)0.0022 (9)
C9A0.0204 (12)0.0110 (11)0.0235 (13)0.0023 (9)0.0066 (10)0.0004 (9)
C10A0.0183 (12)0.0135 (12)0.0239 (13)0.0027 (9)0.0076 (10)0.0012 (9)
C11A0.0252 (14)0.0117 (12)0.0409 (17)0.0033 (11)0.0124 (12)0.0063 (11)
S1B0.0341 (4)0.0078 (3)0.0424 (4)0.0005 (3)0.0175 (3)0.0010 (3)
O1B0.0184 (10)0.0305 (13)0.084 (2)0.0083 (9)0.0201 (11)0.0189 (12)
O2B0.0283 (11)0.0157 (10)0.0526 (14)0.0077 (9)0.0109 (10)0.0033 (9)
O3B0.0201 (9)0.0125 (9)0.0339 (11)0.0004 (7)0.0098 (8)0.0006 (7)
N1B0.0234 (12)0.0125 (12)0.0452 (16)0.0068 (10)0.0108 (11)0.0016 (10)
N2B0.0198 (11)0.0070 (9)0.0268 (12)0.0001 (8)0.0095 (9)0.0000 (8)
N3B0.0179 (10)0.0099 (10)0.0269 (12)0.0006 (8)0.0074 (9)0.0000 (8)
N4B0.0198 (11)0.0116 (10)0.0204 (11)0.0015 (8)0.0067 (9)0.0020 (8)
N5B0.0173 (10)0.0124 (10)0.0266 (12)0.0007 (8)0.0061 (9)0.0008 (8)
N6B0.0201 (11)0.0223 (13)0.0327 (13)0.0078 (10)0.0123 (10)0.0054 (10)
C1B0.0275 (14)0.0096 (11)0.0245 (14)0.0057 (10)0.0087 (11)0.0021 (9)
C2B0.0197 (12)0.0091 (11)0.0211 (13)0.0008 (9)0.0081 (10)0.0035 (9)
C3B0.0168 (12)0.0098 (11)0.0235 (13)0.0019 (9)0.0074 (10)0.0010 (9)
C4B0.0192 (12)0.0093 (11)0.0214 (12)0.0007 (9)0.0069 (10)0.0001 (9)
C5B0.0173 (12)0.0143 (12)0.0186 (12)0.0024 (9)0.0057 (9)0.0006 (9)
C6B0.0210 (13)0.0135 (12)0.0250 (13)0.0005 (10)0.0061 (10)0.0034 (10)
C7B0.0177 (12)0.0206 (13)0.0238 (13)0.0009 (10)0.0075 (10)0.0050 (10)
C8B0.0216 (13)0.0163 (13)0.0226 (13)0.0070 (10)0.0095 (10)0.0022 (10)
C9B0.0243 (13)0.0130 (12)0.0257 (14)0.0021 (10)0.0088 (11)0.0008 (10)
C10B0.0177 (12)0.0139 (12)0.0244 (13)0.0010 (10)0.0074 (10)0.0015 (10)
C11B0.0202 (13)0.0116 (12)0.0366 (16)0.0009 (10)0.0083 (11)0.0023 (10)
Geometric parameters (Å, º) top
S1A—C1A1.665 (3)S1B—C1B1.660 (3)
O1A—N6A1.226 (3)O1B—N6B1.227 (3)
O2A—N6A1.227 (3)O2B—N6B1.228 (3)
O3A—C2A1.218 (3)O3B—C2B1.223 (3)
N1A—C1A1.324 (4)N1B—C1B1.322 (4)
N1A—H2N10.85 (4)N1B—H4N10.84 (4)
N1A—H1N10.88 (4)N1B—H3N10.86 (4)
N2A—C1A1.401 (3)N2B—C2B1.389 (3)
N2A—C2A1.401 (3)N2B—C1B1.418 (3)
N2A—N3A1.425 (3)N2B—N3B1.426 (3)
N3A—C4A1.299 (3)N3B—C4B1.302 (3)
N4A—C3A1.306 (3)N4B—C3B1.305 (3)
N4A—N5A1.312 (3)N4B—N5B1.312 (3)
N5A—C5A1.403 (3)N5B—C5B1.403 (3)
N5A—H1N50.92 (4)N5B—H2N50.98 (4)
N6A—C8A1.465 (3)N6B—C8B1.463 (3)
C2A—C3A1.465 (3)C2B—C3B1.470 (3)
C3A—C4A1.438 (4)C3B—C4B1.439 (3)
C4A—C11A1.492 (4)C4B—C11B1.483 (3)
C5A—C6A1.395 (4)C5B—C6B1.392 (4)
C5A—C10A1.400 (4)C5B—C10B1.401 (4)
C6A—C7A1.383 (4)C6B—C7B1.381 (4)
C6A—H6AA0.9500C6B—H6BA0.9500
C7A—C8A1.383 (4)C7B—C8B1.391 (4)
C7A—H7AA0.9500C7B—H7BA0.9500
C8A—C9A1.396 (4)C8B—C9B1.392 (4)
C9A—C10A1.379 (4)C9B—C10B1.386 (4)
C9A—H9AA0.9500C9B—H9BA0.9500
C10A—H10A0.9500C10B—H10B0.9500
C11A—H11A0.9800C11B—H11D0.9800
C11A—H11B0.9800C11B—H11E0.9800
C11A—H11C0.9800C11B—H11F0.9800
C1A—N1A—H2N1119 (3)C1B—N1B—H4N1117 (3)
C1A—N1A—H1N1122 (3)C1B—N1B—H3N1117 (2)
H2N1—N1A—H1N1117 (4)H4N1—N1B—H3N1125 (4)
C1A—N2A—C2A130.6 (2)C2B—N2B—C1B130.9 (2)
C1A—N2A—N3A117.6 (2)C2B—N2B—N3B112.16 (19)
C2A—N2A—N3A111.77 (19)C1B—N2B—N3B116.9 (2)
C4A—N3A—N2A107.1 (2)C4B—N3B—N2B107.2 (2)
C3A—N4A—N5A118.9 (2)C3B—N4B—N5B119.2 (2)
N4A—N5A—C5A118.6 (2)N4B—N5B—C5B118.8 (2)
N4A—N5A—H1N5121 (2)N4B—N5B—H2N5120 (2)
C5A—N5A—H1N5121 (2)C5B—N5B—H2N5121 (2)
O1A—N6A—O2A123.4 (2)O1B—N6B—O2B123.2 (2)
O1A—N6A—C8A118.4 (2)O1B—N6B—C8B118.3 (2)
O2A—N6A—C8A118.2 (2)O2B—N6B—C8B118.5 (2)
N1A—C1A—N2A113.0 (2)N1B—C1B—N2B112.5 (2)
N1A—C1A—S1A124.1 (2)N1B—C1B—S1B125.2 (2)
N2A—C1A—S1A122.8 (2)N2B—C1B—S1B122.3 (2)
O3A—C2A—N2A130.3 (2)O3B—C2B—N2B130.2 (2)
O3A—C2A—C3A126.7 (2)O3B—C2B—C3B126.8 (2)
N2A—C2A—C3A103.0 (2)N2B—C2B—C3B103.0 (2)
N4A—C3A—C4A124.7 (2)N4B—C3B—C4B124.9 (2)
N4A—C3A—C2A128.5 (2)N4B—C3B—C2B128.3 (2)
C4A—C3A—C2A106.7 (2)C4B—C3B—C2B106.7 (2)
N3A—C4A—C3A111.3 (2)N3B—C4B—C3B111.0 (2)
N3A—C4A—C11A122.5 (2)N3B—C4B—C11B122.9 (2)
C3A—C4A—C11A126.2 (2)C3B—C4B—C11B126.1 (2)
C6A—C5A—C10A121.0 (2)C6B—C5B—C10B121.6 (2)
C6A—C5A—N5A118.6 (2)C6B—C5B—N5B118.6 (2)
C10A—C5A—N5A120.4 (2)C10B—C5B—N5B119.8 (2)
C7A—C6A—C5A119.7 (2)C7B—C6B—C5B120.0 (2)
C7A—C6A—H6AA120.1C7B—C6B—H6BA120.0
C5A—C6A—H6AA120.1C5B—C6B—H6BA120.0
C6A—C7A—C8A118.7 (2)C6B—C7B—C8B118.1 (2)
C6A—C7A—H7AA120.7C6B—C7B—H7BA121.0
C8A—C7A—H7AA120.7C8B—C7B—H7BA121.0
C7A—C8A—C9A122.5 (2)C7B—C8B—C9B122.6 (2)
C7A—C8A—N6A119.1 (2)C7B—C8B—N6B119.0 (2)
C9A—C8A—N6A118.3 (2)C9B—C8B—N6B118.3 (2)
C10A—C9A—C8A118.7 (2)C10B—C9B—C8B119.1 (2)
C10A—C9A—H9AA120.7C10B—C9B—H9BA120.5
C8A—C9A—H9AA120.7C8B—C9B—H9BA120.5
C9A—C10A—C5A119.5 (2)C9B—C10B—C5B118.6 (2)
C9A—C10A—H10A120.3C9B—C10B—H10B120.7
C5A—C10A—H10A120.3C5B—C10B—H10B120.7
C4A—C11A—H11A109.5C4B—C11B—H11D109.5
C4A—C11A—H11B109.5C4B—C11B—H11E109.5
H11A—C11A—H11B109.5H11D—C11B—H11E109.5
C4A—C11A—H11C109.5C4B—C11B—H11F109.5
H11A—C11A—H11C109.5H11D—C11B—H11F109.5
H11B—C11A—H11C109.5H11E—C11B—H11F109.5
C1A—N2A—N3A—C4A179.6 (2)C2B—N2B—N3B—C4B0.5 (3)
C2A—N2A—N3A—C4A1.9 (3)C1B—N2B—N3B—C4B177.9 (2)
C3A—N4A—N5A—C5A179.9 (2)C3B—N4B—N5B—C5B178.2 (2)
C2A—N2A—C1A—N1A176.0 (3)C2B—N2B—C1B—N1B173.6 (3)
N3A—N2A—C1A—N1A1.2 (3)N3B—N2B—C1B—N1B8.4 (3)
C2A—N2A—C1A—S1A4.4 (4)C2B—N2B—C1B—S1B5.8 (4)
N3A—N2A—C1A—S1A178.36 (18)N3B—N2B—C1B—S1B172.19 (18)
C1A—N2A—C2A—O3A0.5 (5)C1B—N2B—C2B—O3B3.6 (5)
N3A—N2A—C2A—O3A177.8 (3)N3B—N2B—C2B—O3B178.3 (3)
C1A—N2A—C2A—C3A179.3 (3)C1B—N2B—C2B—C3B177.4 (3)
N3A—N2A—C2A—C3A2.0 (3)N3B—N2B—C2B—C3B0.7 (3)
N5A—N4A—C3A—C4A179.6 (2)N5B—N4B—C3B—C4B177.4 (2)
N5A—N4A—C3A—C2A2.7 (4)N5B—N4B—C3B—C2B0.7 (4)
O3A—C2A—C3A—N4A4.2 (5)O3B—C2B—C3B—N4B4.4 (5)
N2A—C2A—C3A—N4A176.0 (3)N2B—C2B—C3B—N4B176.5 (3)
O3A—C2A—C3A—C4A178.5 (3)O3B—C2B—C3B—C4B178.4 (3)
N2A—C2A—C3A—C4A1.3 (3)N2B—C2B—C3B—C4B0.7 (3)
N2A—N3A—C4A—C3A0.9 (3)N2B—N3B—C4B—C3B0.0 (3)
N2A—N3A—C4A—C11A179.3 (2)N2B—N3B—C4B—C11B179.9 (2)
N4A—C3A—C4A—N3A177.2 (2)N4B—C3B—C4B—N3B176.9 (3)
C2A—C3A—C4A—N3A0.2 (3)C2B—C3B—C4B—N3B0.4 (3)
N4A—C3A—C4A—C11A4.5 (4)N4B—C3B—C4B—C11B3.0 (4)
C2A—C3A—C4A—C11A178.1 (3)C2B—C3B—C4B—C11B179.7 (3)
N4A—N5A—C5A—C6A169.2 (2)N4B—N5B—C5B—C6B176.3 (2)
N4A—N5A—C5A—C10A9.0 (4)N4B—N5B—C5B—C10B5.8 (4)
C10A—C5A—C6A—C7A1.1 (4)C10B—C5B—C6B—C7B1.8 (4)
N5A—C5A—C6A—C7A177.0 (2)N5B—C5B—C6B—C7B176.1 (2)
C5A—C6A—C7A—C8A0.4 (4)C5B—C6B—C7B—C8B0.1 (4)
C6A—C7A—C8A—C9A0.8 (4)C6B—C7B—C8B—C9B2.0 (4)
C6A—C7A—C8A—N6A175.9 (2)C6B—C7B—C8B—N6B174.6 (2)
O1A—N6A—C8A—C7A12.7 (4)O1B—N6B—C8B—C7B1.2 (4)
O2A—N6A—C8A—C7A165.3 (3)O2B—N6B—C8B—C7B177.0 (3)
O1A—N6A—C8A—C9A170.4 (3)O1B—N6B—C8B—C9B177.9 (3)
O2A—N6A—C8A—C9A11.6 (4)O2B—N6B—C8B—C9B0.3 (4)
C7A—C8A—C9A—C10A0.2 (4)C7B—C8B—C9B—C10B1.9 (4)
N6A—C8A—C9A—C10A177.0 (2)N6B—C8B—C9B—C10B174.7 (2)
C8A—C9A—C10A—C5A1.7 (4)C8B—C9B—C10B—C5B0.1 (4)
C6A—C5A—C10A—C9A2.2 (4)C6B—C5B—C10B—C9B1.9 (4)
N5A—C5A—C10A—C9A175.9 (2)N5B—C5B—C10B—C9B175.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5B—H2N5···O3B0.97 (3)2.08 (3)2.810 (3)131 (3)
N1A—H1N1···O3Bi0.88 (4)2.00 (4)2.859 (3)165 (4)
N5A—H1N5···O3A0.92 (3)2.11 (4)2.802 (3)131 (3)
N1B—H3N1···O3Aii0.87 (3)1.99 (4)2.848 (3)171 (3)
C10B—H10B···O2Aiii0.952.513.418 (3)161
Symmetry codes: (i) x, y1, z; (ii) x1, y+1, z; (iii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC11H10N6O3S
Mr306.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)11.5331 (4), 17.2540 (6), 13.6025 (5)
β (°) 105.840 (2)
V3)2604.01 (16)
Z8
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.23 × 0.19 × 0.13
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.940, 0.965
No. of measured, independent and
observed [I > 2σ(I)] reflections
29927, 7706, 5153
Rint0.086
(sin θ/λ)max1)0.708
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.187, 1.05
No. of reflections7706
No. of parameters405
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.17, 0.45

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
N5B—H2N5···O3B0.97 (3)2.08 (3)2.810 (3)131 (3)
N1A—H1N1···O3Bi0.88 (4)2.00 (4)2.859 (3)165 (4)
N5A—H1N5···O3A0.92 (3)2.11 (4)2.802 (3)131 (3)
N1B—H3N1···O3Aii0.87 (3)1.99 (4)2.848 (3)171 (3)
C10B—H10B···O2Aiii0.95002.51003.418 (3)161.00
Symmetry codes: (i) x, y1, z; (ii) x1, y+1, z; (iii) x1, y, z.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). CKQ also thanks USM for an Incentive Grant.

References

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