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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3050–o3051.
Published online 2010 November 6. doi:  10.1107/S1600536810044181
PMCID: PMC3011737

5-Isobutyl-4-phenyl­sulfonyl-1H-pyrazol-3(2H)-one

Abstract

The title compound, C13H16N2O3S, consists of two crystallographically independent mol­ecules with similar geometries and exists in a keto form, the C=O bond lengths being 1.267 (2) and 1.254 (2) Å. In both mol­ecules, the pyrazole rings are approximately planar, with maximum deviations of 0.017 (2) and 0.010 (2) Å, and the dihedral angles between the pyrazole and phenyl rings are 83.63 (11) and 70.07 (12)°. In one mol­ecule, an intra­molecular C—H(...)O hydrogen bond with an S(6) ring motif is observed. In the crystal, inter­molecular N—H(...)O and C—H(...)O hydrogen bonds link the mol­ecules into two-dimensional networks parallel to the ab plane.

Related literature

For background to pyrazole derivatives and their microbial activities, see: Ragavan et al. (2009 [triangle], 2010 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For related structures, see: Loh, Fun, Ragavan, Vijayakumar & Sarveswari (2010 [triangle]); Loh, Fun, Ragavan, Vijayakumar & Venkatesh (2010 [triangle]); Shahani et al. (2010 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3050-scheme1.jpg

Experimental

Crystal data

  • C13H16N2O3S
  • M r = 280.34
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3050-efi1.jpg
  • a = 11.3423 (8) Å
  • b = 11.9987 (9) Å
  • c = 12.4657 (9) Å
  • α = 98.579 (3)°
  • β = 113.038 (3)°
  • γ = 112.882 (3)°
  • V = 1344.42 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.25 mm−1
  • T = 100 K
  • 0.56 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.875, T max = 0.958
  • 18458 measured reflections
  • 5202 independent reflections
  • 4816 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.109
  • S = 1.04
  • 5202 reflections
  • 363 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.67 e Å−3
  • Δρmin = −0.38 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044181/is2619sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044181/is2619Isup2.hkl

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

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (grant No. 1001/PFIZIK/811160). WSL also thanks the Malaysian government and USM for the award of a research fellowship. VV is grateful to DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

supplementary crystallographic information

Comment

Antibacterial and antifungal activities of the azoles are most widely studied and some of them are in clinical practice as anti-microbial agents. However, the azole-resistant strains had led to the development of new anti-microbial compounds. In particular, pyrazole derivatives are extensively studied and used as anti-microbial agents. Pyrazole is an important class of heterocyclic compounds and many pyrazole derivatives are reported to have the broad spectrum of biological properties such as anti-inflammatory, antifungal, herbicidal, anti-tumour, cytotoxic, molecular modelling and antiviral activities. Pyrazole derivatives also act as anti-angiogenic agents, A3 adenosine receptor antagonists, neuropeptide YY5 receptor antagonists as well as kinase inhibitor for treatment of type 2 diabetes, hyperlipidemia, obesity and thrombopiotinmimetics. Recently urea derivatives of pyrazoles have been reported as potent inhibitors of p38 kinase. Since the high electronegativity of halogens (particularly chlorine and fluorine) in the aromatic part of the drug molecules play an important role in enhancing their biological activity, we are interested to have 4-fluoro or 4-chloro substitution in the aryls of 1,5-diaryl pyrazoles. As part of our on-going research aiming the synthesis of new anti-microbial compounds, we have reported the synthesis of novel pyrazole derivatives and their microbial activities (Ragavan et al., 2009, 2010).

The title compound consists of two crystallographically independent molecules, with similar geometries, namely molecules A and B and exist in keto-form. This indicates that the compound undergoes an enol-to-keto tautomerism during the crystallization process with the bond lengths of C═ O being 1.267 (2) and 1.254 (2) Å in molecule A and B, respectively. In molecule A, the pyrazole ring (C7A/C8A/N1A/N2A/C9A) is approximately planar with a maximum deviation of 0.017 (2) Å at atom C7A and almost perpendicular with the phenyl ring (C1A–C6A) with a dihedral angle of 83.63 (11)°. In molecule B, the pyrazole ring (C7B/C8B/N1B/N2B/C9B) with a maximum deviation being 0.010 (2) Å at C8B forms a dihedral angle of 70.07 (12)° with the phenyl ring (C1B–C6B) and further stabilized by an S(6) ring motif (Bernstein et al., 1995) via the intramolecular C10B—H10D···O1B hydrogen bond. Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the related structures (Loh, Fun, Ragavan, Vijayakumar & Sarveswari, 2010; Loh, Fun, Ragavan, Vijayakumar & Venkatesh, 2010; Shahani et al., 2010).

In the crystal packing, intermolecular N1A—H1NA···O3A, N2A—H2NA···O3B, N1B—H1NB···O1A, N2B—H2NB···O3A, C5A—H5AA···O1B, C5B—H5BA···O2A and C10A—H10B···O3B hydrogen bonds (Table 1) link the molecules into two-dimensional networks parallel to ab plane (Fig. 2).

Experimental

3-Isobutyl-4-(phenylthiol)-1H-pyrazol-5-ol was synthesized using the method available in the literature (Ragavan et al., 2010). It was then dissolved in 1:1 mixture of THF/Water. Oxone was then added and the solution was stirred at room temperature for 3 h. The reaction mixture was diluted with water (20 ml) and then extracted with ethylacetate (2 x 50 ml). The combined extract was washed with water (20 ml) and brine solution. The titled compound was recrystallized using the ethanol-chloroform 1:1 mixture. Yield: 50%. M. p. = 487–489 K.

Refinement

N-bound H atoms were located in a difference Fourier map and was refined freely [N—H = 0.79 (3) to 0.88 (3) Å]. The remaining H atoms were positioned geometrically with the bond length of C—H being 0.93 to 0.98 Å and were refined using a riding model, with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to the methyl groups.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. The dashed line indicates the intramolecular hydrogen bond.
Fig. 2.
The crystal packing of the title compound, showing two-dimensional networks parallel to the ab plane. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Crystal data

C13H16N2O3SZ = 4
Mr = 280.34F(000) = 592
Triclinic, P1Dx = 1.385 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.3423 (8) ÅCell parameters from 9939 reflections
b = 11.9987 (9) Åθ = 2.6–35.0°
c = 12.4657 (9) ŵ = 0.25 mm1
α = 98.579 (3)°T = 100 K
β = 113.038 (3)°Block, colourless
γ = 112.882 (3)°0.56 × 0.20 × 0.18 mm
V = 1344.42 (17) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer5202 independent reflections
Radiation source: fine-focus sealed tube4816 reflections with I > 2σ(I)
graphiteRint = 0.034
[var phi] and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −13→13
Tmin = 0.875, Tmax = 0.958k = −14→14
18458 measured reflectionsl = −15→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0553P)2 + 1.2051P] where P = (Fo2 + 2Fc2)/3
5202 reflections(Δ/σ)max = 0.001
363 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = −0.38 e Å3

Special details

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 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)

xyzUiso*/Ueq
S1A0.61779 (4)0.56939 (4)0.30323 (4)0.01287 (12)
O1A0.52206 (14)0.62292 (12)0.29583 (12)0.0177 (3)
O2A0.56191 (14)0.44944 (12)0.20809 (11)0.0176 (3)
O3A0.81177 (13)0.88563 (12)0.44040 (11)0.0155 (3)
N1A0.96797 (17)0.87383 (15)0.36853 (14)0.0144 (3)
N2A0.97863 (17)0.77840 (15)0.30426 (13)0.0146 (3)
C1A0.7407 (2)0.46688 (18)0.46562 (17)0.0190 (4)
H1AA0.74150.41990.39960.023*
C2A0.7970 (2)0.45448 (19)0.58116 (18)0.0223 (4)
H2AA0.83690.39980.59340.027*
C3A0.7936 (2)0.52380 (19)0.67853 (17)0.0221 (4)
H3AA0.83170.51570.75610.027*
C4A0.7335 (2)0.60524 (19)0.66063 (17)0.0227 (4)
H4AA0.72990.64990.72590.027*
C5A0.6789 (2)0.62047 (18)0.54597 (17)0.0192 (4)
H5AA0.64050.67620.53410.023*
C6A0.68325 (19)0.55035 (16)0.44963 (16)0.0144 (3)
C7A0.77240 (19)0.68499 (17)0.31001 (15)0.0137 (3)
C8A0.84468 (18)0.82068 (16)0.37900 (15)0.0128 (3)
C9A0.86263 (19)0.66367 (17)0.26817 (15)0.0132 (3)
C10A0.84569 (19)0.54146 (17)0.19624 (15)0.0155 (3)
H10A0.80840.47430.22770.019*
H10B0.94180.55590.21070.019*
C11A0.7416 (2)0.49321 (18)0.05437 (16)0.0190 (4)
H11A0.65100.49440.04070.023*
C12A0.7026 (3)0.3539 (2)−0.0044 (2)0.0394 (6)
H12A0.63530.3223−0.09220.059*
H12B0.65760.30060.03370.059*
H12C0.79050.35110.00840.059*
C13A0.8111 (2)0.5804 (2)−0.00512 (18)0.0249 (4)
H13A0.74270.5505−0.09240.037*
H13B0.89860.57840.00540.037*
H13C0.83580.66750.03410.037*
S1B0.32612 (5)0.06328 (4)0.30231 (4)0.01364 (12)
O1B0.44172 (14)0.19562 (12)0.37062 (12)0.0203 (3)
O2B0.20554 (14)0.01636 (13)0.32778 (12)0.0184 (3)
O3B0.18314 (13)−0.24470 (12)0.26728 (12)0.0177 (3)
N1B0.41780 (16)−0.21360 (15)0.33582 (14)0.0156 (3)
N2B0.55364 (17)−0.11548 (15)0.36901 (14)0.0158 (3)
C1B0.1298 (2)−0.07887 (19)0.05619 (17)0.0221 (4)
H1BA0.0925−0.14620.08270.026*
C2B0.0666 (2)−0.0952 (2)−0.06954 (19)0.0300 (5)
H2BA−0.0139−0.1743−0.12800.036*
C3B0.1230 (3)0.0058 (2)−0.10850 (19)0.0320 (5)
H3BA0.0792−0.0057−0.19280.038*
C4B0.2432 (3)0.1227 (2)−0.0231 (2)0.0304 (5)
H4BA0.28100.1893−0.05020.036*
C5B0.3091 (2)0.14218 (19)0.10415 (19)0.0224 (4)
H5BA0.39040.22110.16230.027*
C6B0.2500 (2)0.04043 (18)0.14147 (16)0.0163 (4)
C7B0.40072 (19)−0.03787 (17)0.32486 (15)0.0135 (3)
C8B0.31688 (19)−0.17245 (17)0.30481 (15)0.0141 (3)
C9B0.54630 (19)−0.00867 (17)0.36371 (15)0.0139 (3)
C10B0.68105 (19)0.11342 (17)0.39661 (16)0.0166 (4)
H10C0.75810.13240.47880.020*
H10D0.65920.18400.40090.020*
C11B0.7392 (2)0.10832 (19)0.30404 (17)0.0207 (4)
H11B0.75860.03550.29870.025*
C12B0.6260 (2)0.0862 (3)0.1743 (2)0.0346 (5)
H12D0.66460.08250.11850.052*
H12E0.60430.15600.17770.052*
H12F0.53760.00600.14490.052*
C13B0.8834 (2)0.2320 (2)0.3531 (2)0.0273 (4)
H13D0.92170.22720.29730.041*
H13E0.95280.24240.43420.041*
H13F0.86660.30470.35880.041*
H1NA1.035 (3)0.944 (3)0.412 (2)0.028 (6)*
H2NA1.054 (3)0.795 (2)0.296 (2)0.032 (7)*
H1NB0.407 (3)−0.289 (3)0.332 (2)0.026 (6)*
H2NB0.632 (3)−0.125 (2)0.390 (2)0.026 (6)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S1A0.0104 (2)0.0121 (2)0.0158 (2)0.00489 (17)0.00692 (16)0.00437 (16)
O1A0.0132 (6)0.0178 (6)0.0253 (6)0.0090 (5)0.0106 (5)0.0082 (5)
O2A0.0161 (6)0.0136 (6)0.0181 (6)0.0045 (5)0.0079 (5)0.0026 (5)
O3A0.0119 (6)0.0154 (6)0.0190 (6)0.0073 (5)0.0082 (5)0.0027 (5)
N1A0.0108 (7)0.0123 (7)0.0174 (7)0.0041 (6)0.0074 (6)0.0020 (6)
N2A0.0122 (7)0.0164 (7)0.0168 (7)0.0072 (6)0.0088 (6)0.0043 (6)
C1A0.0214 (9)0.0169 (9)0.0207 (9)0.0096 (8)0.0121 (8)0.0060 (7)
C2A0.0231 (10)0.0194 (9)0.0233 (9)0.0108 (8)0.0095 (8)0.0090 (7)
C3A0.0208 (10)0.0221 (9)0.0176 (8)0.0054 (8)0.0087 (7)0.0091 (7)
C4A0.0219 (10)0.0241 (10)0.0194 (9)0.0075 (8)0.0131 (8)0.0039 (7)
C5A0.0176 (9)0.0176 (9)0.0222 (9)0.0073 (7)0.0118 (7)0.0047 (7)
C6A0.0124 (8)0.0133 (8)0.0167 (8)0.0040 (7)0.0085 (7)0.0060 (6)
C7A0.0124 (8)0.0143 (8)0.0156 (8)0.0069 (7)0.0076 (7)0.0056 (6)
C8A0.0103 (8)0.0158 (8)0.0122 (7)0.0069 (7)0.0047 (6)0.0058 (6)
C9A0.0129 (8)0.0157 (8)0.0123 (7)0.0077 (7)0.0062 (6)0.0063 (6)
C10A0.0152 (8)0.0156 (8)0.0166 (8)0.0080 (7)0.0085 (7)0.0046 (7)
C11A0.0199 (9)0.0199 (9)0.0149 (8)0.0090 (8)0.0081 (7)0.0038 (7)
C12A0.0616 (17)0.0238 (11)0.0218 (10)0.0181 (11)0.0157 (11)0.0026 (9)
C13A0.0250 (10)0.0301 (11)0.0193 (9)0.0120 (9)0.0117 (8)0.0098 (8)
S1B0.0122 (2)0.0146 (2)0.0157 (2)0.00772 (18)0.00735 (17)0.00464 (16)
O1B0.0167 (7)0.0157 (6)0.0240 (6)0.0081 (6)0.0075 (5)0.0024 (5)
O2B0.0166 (6)0.0225 (7)0.0225 (6)0.0122 (6)0.0126 (5)0.0085 (5)
O3B0.0127 (6)0.0190 (6)0.0234 (6)0.0082 (5)0.0103 (5)0.0073 (5)
N1B0.0123 (7)0.0151 (8)0.0222 (7)0.0075 (6)0.0098 (6)0.0079 (6)
N2B0.0108 (7)0.0185 (8)0.0188 (7)0.0082 (6)0.0072 (6)0.0062 (6)
C1B0.0190 (9)0.0246 (10)0.0216 (9)0.0102 (8)0.0099 (8)0.0078 (8)
C2B0.0224 (10)0.0404 (12)0.0197 (9)0.0156 (10)0.0064 (8)0.0032 (9)
C3B0.0368 (12)0.0576 (15)0.0221 (10)0.0364 (12)0.0170 (9)0.0209 (10)
C4B0.0405 (13)0.0420 (13)0.0377 (11)0.0315 (11)0.0284 (10)0.0290 (10)
C5B0.0237 (10)0.0226 (10)0.0306 (10)0.0150 (8)0.0167 (8)0.0140 (8)
C6B0.0154 (9)0.0207 (9)0.0179 (8)0.0123 (8)0.0088 (7)0.0083 (7)
C7B0.0127 (8)0.0155 (8)0.0144 (8)0.0081 (7)0.0075 (6)0.0055 (6)
C8B0.0147 (9)0.0182 (9)0.0136 (8)0.0097 (7)0.0089 (7)0.0061 (7)
C9B0.0137 (8)0.0173 (8)0.0121 (7)0.0078 (7)0.0075 (7)0.0050 (6)
C10B0.0132 (8)0.0172 (9)0.0186 (8)0.0069 (7)0.0081 (7)0.0055 (7)
C11B0.0183 (9)0.0235 (10)0.0248 (9)0.0110 (8)0.0133 (8)0.0098 (8)
C12B0.0247 (11)0.0568 (15)0.0258 (10)0.0180 (11)0.0156 (9)0.0195 (10)
C13B0.0229 (10)0.0261 (10)0.0363 (11)0.0103 (9)0.0191 (9)0.0120 (9)

Geometric parameters (Å, °)

S1A—O2A1.4397 (13)S1B—O1B1.4385 (13)
S1A—O1A1.4428 (13)S1B—O2B1.4431 (13)
S1A—C7A1.7215 (18)S1B—C7B1.7269 (17)
S1A—C6A1.7691 (17)S1B—C6B1.7713 (18)
O3A—C8A1.267 (2)O3B—C8B1.254 (2)
N1A—C8A1.361 (2)N1B—C8B1.362 (2)
N1A—N2A1.370 (2)N1B—N2B1.370 (2)
N1A—H1NA0.79 (3)N1B—H1NB0.86 (3)
N2A—C9A1.331 (2)N2B—C9B1.326 (2)
N2A—H2NA0.84 (3)N2B—H2NB0.88 (3)
C1A—C2A1.386 (3)C1B—C2B1.389 (3)
C1A—C6A1.390 (3)C1B—C6B1.390 (3)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.388 (3)C2B—C3B1.389 (3)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.390 (3)C3B—C4B1.375 (3)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.390 (3)C4B—C5B1.398 (3)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.389 (2)C5B—C6B1.391 (3)
C5A—H5AA0.9300C5B—H5BA0.9300
C7A—C9A1.402 (2)C7B—C9B1.399 (2)
C7A—C8A1.433 (2)C7B—C8B1.440 (2)
C9A—C10A1.498 (2)C9B—C10B1.496 (2)
C10A—C11A1.544 (2)C10B—C11B1.541 (2)
C10A—H10A0.9700C10B—H10C0.9700
C10A—H10B0.9700C10B—H10D0.9700
C11A—C13A1.521 (3)C11B—C13B1.520 (3)
C11A—C12A1.528 (3)C11B—C12B1.522 (3)
C11A—H11A0.9800C11B—H11B0.9800
C12A—H12A0.9600C12B—H12D0.9600
C12A—H12B0.9600C12B—H12E0.9600
C12A—H12C0.9600C12B—H12F0.9600
C13A—H13A0.9600C13B—H13D0.9600
C13A—H13B0.9600C13B—H13E0.9600
C13A—H13C0.9600C13B—H13F0.9600
O2A—S1A—O1A119.07 (8)O1B—S1B—O2B118.68 (8)
O2A—S1A—C7A108.50 (8)O1B—S1B—C7B109.29 (8)
O1A—S1A—C7A107.89 (8)O2B—S1B—C7B106.75 (8)
O2A—S1A—C6A108.27 (8)O1B—S1B—C6B107.72 (8)
O1A—S1A—C6A107.77 (8)O2B—S1B—C6B107.22 (8)
C7A—S1A—C6A104.39 (8)C7B—S1B—C6B106.56 (8)
C8A—N1A—N2A109.89 (14)C8B—N1B—N2B110.67 (15)
C8A—N1A—H1NA123.5 (19)C8B—N1B—H1NB130.6 (16)
N2A—N1A—H1NA123.7 (19)N2B—N1B—H1NB118.5 (16)
C9A—N2A—N1A110.01 (15)C9B—N2B—N1B109.61 (15)
C9A—N2A—H2NA128.6 (17)C9B—N2B—H2NB126.7 (16)
N1A—N2A—H2NA121.2 (17)N1B—N2B—H2NB123.7 (16)
C2A—C1A—C6A119.19 (16)C2B—C1B—C6B118.48 (19)
C2A—C1A—H1AA120.4C2B—C1B—H1BA120.8
C6A—C1A—H1AA120.4C6B—C1B—H1BA120.8
C1A—C2A—C3A119.87 (18)C3B—C2B—C1B120.4 (2)
C1A—C2A—H2AA120.1C3B—C2B—H2BA119.8
C3A—C2A—H2AA120.1C1B—C2B—H2BA119.8
C2A—C3A—C4A120.31 (17)C4B—C3B—C2B120.35 (19)
C2A—C3A—H3AA119.8C4B—C3B—H3BA119.8
C4A—C3A—H3AA119.8C2B—C3B—H3BA119.8
C3A—C4A—C5A120.56 (17)C3B—C4B—C5B120.6 (2)
C3A—C4A—H4AA119.7C3B—C4B—H4BA119.7
C5A—C4A—H4AA119.7C5B—C4B—H4BA119.7
C6A—C5A—C4A118.31 (17)C6B—C5B—C4B118.23 (19)
C6A—C5A—H5AA120.8C6B—C5B—H5BA120.9
C4A—C5A—H5AA120.8C4B—C5B—H5BA120.9
C5A—C6A—C1A121.74 (16)C1B—C6B—C5B121.91 (17)
C5A—C6A—S1A119.60 (14)C1B—C6B—S1B118.50 (14)
C1A—C6A—S1A118.65 (13)C5B—C6B—S1B119.57 (14)
C9A—C7A—C8A107.66 (15)C9B—C7B—C8B107.90 (15)
C9A—C7A—S1A127.02 (14)C9B—C7B—S1B128.47 (14)
C8A—C7A—S1A124.58 (13)C8B—C7B—S1B123.63 (13)
O3A—C8A—N1A123.49 (16)O3B—C8B—N1B123.41 (16)
O3A—C8A—C7A131.50 (16)O3B—C8B—C7B132.46 (16)
N1A—C8A—C7A105.00 (14)N1B—C8B—C7B104.14 (15)
N2A—C9A—C7A107.31 (15)N2B—C9B—C7B107.66 (16)
N2A—C9A—C10A121.56 (15)N2B—C9B—C10B120.20 (16)
C7A—C9A—C10A131.14 (16)C7B—C9B—C10B132.14 (16)
C9A—C10A—C11A113.81 (14)C9B—C10B—C11B114.21 (15)
C9A—C10A—H10A108.8C9B—C10B—H10C108.7
C11A—C10A—H10A108.8C11B—C10B—H10C108.7
C9A—C10A—H10B108.8C9B—C10B—H10D108.7
C11A—C10A—H10B108.8C11B—C10B—H10D108.7
H10A—C10A—H10B107.7H10C—C10B—H10D107.6
C13A—C11A—C12A111.09 (17)C13B—C11B—C12B111.52 (17)
C13A—C11A—C10A111.16 (15)C13B—C11B—C10B109.50 (16)
C12A—C11A—C10A109.05 (16)C12B—C11B—C10B111.26 (16)
C13A—C11A—H11A108.5C13B—C11B—H11B108.1
C12A—C11A—H11A108.5C12B—C11B—H11B108.1
C10A—C11A—H11A108.5C10B—C11B—H11B108.1
C11A—C12A—H12A109.5C11B—C12B—H12D109.5
C11A—C12A—H12B109.5C11B—C12B—H12E109.5
H12A—C12A—H12B109.5H12D—C12B—H12E109.5
C11A—C12A—H12C109.5C11B—C12B—H12F109.5
H12A—C12A—H12C109.5H12D—C12B—H12F109.5
H12B—C12A—H12C109.5H12E—C12B—H12F109.5
C11A—C13A—H13A109.5C11B—C13B—H13D109.5
C11A—C13A—H13B109.5C11B—C13B—H13E109.5
H13A—C13A—H13B109.5H13D—C13B—H13E109.5
C11A—C13A—H13C109.5C11B—C13B—H13F109.5
H13A—C13A—H13C109.5H13D—C13B—H13F109.5
H13B—C13A—H13C109.5H13E—C13B—H13F109.5
C8A—N1A—N2A—C9A2.14 (19)C8B—N1B—N2B—C9B1.50 (19)
C6A—C1A—C2A—C3A0.8 (3)C6B—C1B—C2B—C3B0.1 (3)
C1A—C2A—C3A—C4A0.3 (3)C1B—C2B—C3B—C4B0.8 (3)
C2A—C3A—C4A—C5A−1.3 (3)C2B—C3B—C4B—C5B−0.9 (3)
C3A—C4A—C5A—C6A1.3 (3)C3B—C4B—C5B—C6B0.1 (3)
C4A—C5A—C6A—C1A−0.2 (3)C2B—C1B—C6B—C5B−0.9 (3)
C4A—C5A—C6A—S1A−178.87 (14)C2B—C1B—C6B—S1B177.62 (15)
C2A—C1A—C6A—C5A−0.8 (3)C4B—C5B—C6B—C1B0.8 (3)
C2A—C1A—C6A—S1A177.83 (15)C4B—C5B—C6B—S1B−177.67 (14)
O2A—S1A—C6A—C5A−150.20 (15)O1B—S1B—C6B—C1B−176.39 (14)
O1A—S1A—C6A—C5A−20.19 (17)O2B—S1B—C6B—C1B−47.59 (16)
C7A—S1A—C6A—C5A94.35 (16)C7B—S1B—C6B—C1B66.43 (16)
O2A—S1A—C6A—C1A31.11 (16)O1B—S1B—C6B—C5B2.15 (17)
O1A—S1A—C6A—C1A161.12 (14)O2B—S1B—C6B—C5B130.95 (15)
C7A—S1A—C6A—C1A−84.34 (15)C7B—S1B—C6B—C5B−115.03 (15)
O2A—S1A—C7A—C9A−21.55 (18)O1B—S1B—C7B—C9B−20.70 (18)
O1A—S1A—C7A—C9A−151.82 (15)O2B—S1B—C7B—C9B−150.22 (15)
C6A—S1A—C7A—C9A93.73 (16)C6B—S1B—C7B—C9B95.44 (16)
O2A—S1A—C7A—C8A169.54 (14)O1B—S1B—C7B—C8B159.51 (14)
O1A—S1A—C7A—C8A39.28 (16)O2B—S1B—C7B—C8B29.99 (16)
C6A—S1A—C7A—C8A−75.18 (16)C6B—S1B—C7B—C8B−84.35 (15)
N2A—N1A—C8A—O3A175.65 (15)N2B—N1B—C8B—O3B177.71 (15)
N2A—N1A—C8A—C7A−3.48 (18)N2B—N1B—C8B—C7B−1.81 (18)
C9A—C7A—C8A—O3A−175.45 (17)C9B—C7B—C8B—O3B−177.96 (17)
S1A—C7A—C8A—O3A−4.7 (3)S1B—C7B—C8B—O3B1.9 (3)
C9A—C7A—C8A—N1A3.59 (18)C9B—C7B—C8B—N1B1.50 (18)
S1A—C7A—C8A—N1A174.31 (12)S1B—C7B—C8B—N1B−178.68 (12)
N1A—N2A—C9A—C7A0.25 (19)N1B—N2B—C9B—C7B−0.46 (19)
N1A—N2A—C9A—C10A−179.75 (15)N1B—N2B—C9B—C10B179.60 (14)
C8A—C7A—C9A—N2A−2.40 (19)C8B—C7B—C9B—N2B−0.66 (19)
S1A—C7A—C9A—N2A−172.83 (13)S1B—C7B—C9B—N2B179.53 (13)
C8A—C7A—C9A—C10A177.60 (16)C8B—C7B—C9B—C10B179.26 (17)
S1A—C7A—C9A—C10A7.2 (3)S1B—C7B—C9B—C10B−0.5 (3)
N2A—C9A—C10A—C11A−99.45 (19)N2B—C9B—C10B—C11B67.8 (2)
C7A—C9A—C10A—C11A80.6 (2)C7B—C9B—C10B—C11B−112.2 (2)
C9A—C10A—C11A—C13A71.2 (2)C9B—C10B—C11B—C13B−174.69 (16)
C9A—C10A—C11A—C12A−166.01 (17)C9B—C10B—C11B—C12B61.6 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1A—H1NA···O3Ai0.79 (3)2.05 (3)2.816 (2)164 (3)
N2A—H2NA···O3Bii0.85 (4)1.85 (4)2.640 (3)155 (2)
N1B—H1NB···O1Aiii0.86 (3)2.10 (4)2.733 (3)130 (3)
N2B—H2NB···O3Aiii0.88 (4)1.83 (4)2.700 (3)170 (2)
C5A—H5AA···O1Biv0.932.473.256 (3)143
C5B—H5BA···O2A0.932.483.307 (3)149
C10A—H10B···O3Bii0.972.573.324 (3)135
C10B—H10D···O1B0.972.413.152 (3)133

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2619).

References

  • 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.
  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst.19, 105–107.
  • Loh, W.-S., Fun, H.-K., Ragavan, R. V., Vijayakumar, V. & Sarveswari, S. (2010). Acta Cryst. E66, o2925. [PMC free article] [PubMed]
  • Loh, W.-S., Fun, H.-K., Ragavan, R. V., Vijayakumar, V. & Venkatesh, M. (2010). Acta Cryst. E66, o2563–o2564. [PMC free article] [PubMed]
  • Ragavan, R. V., Vijayakumar, V. & Sucheta Kumari, N. (2009). Eur. J. Med. Chem.44, 3852–3857. [PubMed]
  • Ragavan, R. V., Vijayakumar, V. & Sucheta Kumari, N. (2010). Eur. J. Med. Chem.45, 1173–1180. [PubMed]
  • Shahani, T., Fun, H.-K., Ragavan, R. V., Vijayakumar, V. & Sarveswari, S. (2010). Acta Cryst. E66, o1482–o1483. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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