organic compounds
4-Methyl-3-phenyl-2,4-dihydropyrazolo[4,3-c][1,2]benzothiazine 5,5-dioxide†
aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, bDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan, cApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, Pakistan, and dDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
*Correspondence e-mail: matloob_123@yahoo.com
In the title molecule, C16H13N3O2S, the heterocyclic thiazine ring adopts a twist chair conformation with the S atom and an adjacent C atom displaced by 0.946 (5) and 0.405 (6) Å, respectively, on the same side of the mean plane formed by the remaining ring atoms. The mean planes of the benzene rings make dihedral angles of 16.61 (10) and 15.32 (10)° with the mean plane of the pyrazole ring. The molecular structure is consolidated by intramolecular C—H⋯N interactions and the crystal packing is stabilized by N—H⋯O and C—H⋯N hydrogen bonds. The crystal studied was an with the refined ratio of the twin components being 0.53 (11):0.47 (11).
Related literature
For the biological activity of related compounds, see: Turck et al. (1996); Silverstein et al. (2000); Lombardino et al. (1973); Zinnes et al. (1973); Ahmad et al. (2010a,b). For related structures, see: Siddiqui et al. (2008, 2009).
Experimental
Crystal data
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Data collection: COLLECT (Nonius, 1999); cell DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812033284/yk2066sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812033284/yk2066Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812033284/yk2066Isup3.cml
A mixture of 3-benzoyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine 1,1-dioxide (5.0 g, 0.020 mol), hydrazine hydrate (5 ml) and ethanol (30 ml) was refluxed for 5 h followed by the removal of solvent under vacuum. The residue obtained was washed with cold water to get the title compound as a white crystalline product. Transparent crystals suitable for X-ray crystallographic studies were grown from a CHCl3 solution at room temperature by slow evaporation.
All H atoms were positioned geometrically and refined using a riding model, with N—H = 0.86 Å and C—H = 0.93 and 0.96 Å, for aryl and methyl type H-atoms, respectively. The Uiso(H) were allowed at 1.2Ueq(N/C). An
was not determined as the crystal was a racemic twin with BASF parameter refined to 0.53 (11); 1306 Friedel pairs of reflections were not merged. A low angle reflection (0 1 1) was omitted as it was hindered by the beam stop.Data collection: COLLECT (Nonius, 1999); cell
DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C16H13N3O2S | F(000) = 648 |
Mr = 311.35 | Dx = 1.469 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 1837 reflections |
a = 12.1028 (5) Å | θ = 1.0–27.5° |
b = 16.3934 (7) Å | µ = 0.24 mm−1 |
c = 7.0962 (3) Å | T = 295 K |
V = 1407.93 (10) Å3 | Prism, colourless |
Z = 4 | 0.20 × 0.10 × 0.06 mm |
Nonius KappaCCD diffractometer | 3037 independent reflections |
Radiation source: fine-focus sealed tube | 2798 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
ω and ϕ scans | θmax = 27.5°, θmin = 2.5° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −15→15 |
Tmin = 0.953, Tmax = 0.986 | k = −21→21 |
8451 measured reflections | l = −9→9 |
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)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.112 | w = 1/[σ2(Fo2) + (0.0308P)2 + 1.3942P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
3037 reflections | Δρmax = 0.20 e Å−3 |
201 parameters | Δρmin = −0.24 e Å−3 |
1 restraint | Absolute structure: racemic twin; used 1306 unmerged Friedel pairs (Flack, 1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.53 (11) |
C16H13N3O2S | V = 1407.93 (10) Å3 |
Mr = 311.35 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 12.1028 (5) Å | µ = 0.24 mm−1 |
b = 16.3934 (7) Å | T = 295 K |
c = 7.0962 (3) Å | 0.20 × 0.10 × 0.06 mm |
Nonius KappaCCD diffractometer | 3037 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 2798 reflections with I > 2σ(I) |
Tmin = 0.953, Tmax = 0.986 | Rint = 0.049 |
8451 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.112 | Δρmax = 0.20 e Å−3 |
S = 1.08 | Δρmin = −0.24 e Å−3 |
3037 reflections | Absolute structure: racemic twin; used 1306 unmerged Friedel pairs (Flack, 1983) |
201 parameters | Absolute structure parameter: 0.53 (11) |
1 restraint |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 | ||
S1 | 0.68932 (5) | −0.05378 (4) | 0.08389 (12) | 0.03515 (17) | |
O1 | 0.57190 (16) | −0.05177 (14) | 0.1024 (4) | 0.0499 (6) | |
O2 | 0.73666 (18) | −0.03884 (14) | −0.0982 (3) | 0.0431 (5) | |
N1 | 0.74275 (18) | 0.01482 (14) | 0.2279 (4) | 0.0337 (5) | |
N2 | 1.03707 (18) | 0.01490 (15) | 0.2736 (4) | 0.0382 (6) | |
H2N | 1.1019 | 0.0358 | 0.2852 | 0.046* | |
N3 | 1.0195 (2) | −0.06632 (14) | 0.2734 (4) | 0.0390 (6) | |
C1 | 0.7415 (2) | −0.14793 (18) | 0.1673 (4) | 0.0358 (6) | |
C2 | 0.6783 (3) | −0.2185 (2) | 0.1532 (5) | 0.0440 (8) | |
H2 | 0.6065 | −0.2164 | 0.1068 | 0.053* | |
C3 | 0.7239 (3) | −0.2915 (2) | 0.2091 (5) | 0.0495 (8) | |
H3 | 0.6826 | −0.3392 | 0.1997 | 0.059* | |
C4 | 0.8309 (3) | −0.29478 (19) | 0.2793 (5) | 0.0478 (8) | |
H4 | 0.8610 | −0.3447 | 0.3148 | 0.057* | |
C5 | 0.8928 (3) | −0.22450 (18) | 0.2968 (5) | 0.0408 (7) | |
H5 | 0.9637 | −0.2271 | 0.3471 | 0.049* | |
C6 | 0.8497 (2) | −0.14990 (17) | 0.2397 (4) | 0.0332 (6) | |
C7 | 0.9096 (2) | −0.07256 (17) | 0.2537 (4) | 0.0327 (6) | |
C8 | 0.8602 (2) | 0.00418 (16) | 0.2414 (4) | 0.0307 (6) | |
C9 | 0.9449 (2) | 0.06124 (16) | 0.2543 (4) | 0.0324 (6) | |
C10 | 0.6875 (3) | 0.0225 (2) | 0.4135 (5) | 0.0475 (8) | |
H10A | 0.7147 | 0.0700 | 0.4774 | 0.057* | |
H10B | 0.7027 | −0.0251 | 0.4880 | 0.057* | |
H10C | 0.6092 | 0.0275 | 0.3953 | 0.057* | |
C11 | 0.9476 (2) | 0.15030 (17) | 0.2437 (4) | 0.0330 (6) | |
C12 | 1.0427 (3) | 0.19349 (18) | 0.2942 (5) | 0.0399 (7) | |
H12 | 1.1040 | 0.1658 | 0.3404 | 0.048* | |
C13 | 1.0454 (3) | 0.2779 (2) | 0.2753 (5) | 0.0473 (8) | |
H13 | 1.1087 | 0.3064 | 0.3095 | 0.057* | |
C14 | 0.9552 (3) | 0.31974 (19) | 0.2063 (5) | 0.0466 (8) | |
H14 | 0.9577 | 0.3762 | 0.1935 | 0.056* | |
C15 | 0.8613 (3) | 0.2772 (2) | 0.1563 (5) | 0.0463 (8) | |
H15 | 0.8002 | 0.3051 | 0.1099 | 0.056* | |
C16 | 0.8575 (3) | 0.19346 (19) | 0.1748 (5) | 0.0405 (7) | |
H16 | 0.7937 | 0.1655 | 0.1407 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0238 (3) | 0.0454 (4) | 0.0363 (3) | −0.0041 (3) | −0.0014 (3) | 0.0004 (4) |
O1 | 0.0255 (9) | 0.0642 (14) | 0.0602 (16) | −0.0059 (9) | −0.0010 (12) | −0.0025 (13) |
O2 | 0.0328 (11) | 0.0613 (14) | 0.0351 (12) | −0.0066 (10) | −0.0014 (9) | 0.0053 (11) |
N1 | 0.0255 (11) | 0.0361 (12) | 0.0394 (13) | 0.0005 (9) | 0.0004 (10) | −0.0021 (11) |
N2 | 0.0275 (11) | 0.0361 (12) | 0.0511 (16) | −0.0026 (10) | −0.0064 (11) | 0.0006 (12) |
N3 | 0.0299 (12) | 0.0363 (12) | 0.0508 (16) | 0.0026 (9) | −0.0067 (12) | −0.0013 (12) |
C1 | 0.0328 (14) | 0.0401 (16) | 0.0343 (15) | −0.0047 (12) | 0.0035 (12) | −0.0021 (13) |
C2 | 0.0412 (17) | 0.0538 (19) | 0.0370 (16) | −0.0166 (14) | 0.0052 (14) | −0.0069 (15) |
C3 | 0.060 (2) | 0.0394 (17) | 0.049 (2) | −0.0164 (15) | 0.0029 (17) | −0.0051 (15) |
C4 | 0.062 (2) | 0.0345 (15) | 0.0468 (19) | −0.0032 (14) | 0.0076 (17) | −0.0014 (14) |
C5 | 0.0442 (16) | 0.0382 (16) | 0.0399 (17) | 0.0011 (13) | 0.0043 (14) | 0.0002 (13) |
C6 | 0.0334 (13) | 0.0364 (14) | 0.0298 (14) | −0.0009 (11) | 0.0019 (12) | −0.0022 (12) |
C7 | 0.0282 (13) | 0.0352 (13) | 0.0348 (15) | −0.0003 (11) | −0.0022 (12) | −0.0015 (12) |
C8 | 0.0247 (12) | 0.0365 (14) | 0.0310 (14) | −0.0012 (10) | −0.0027 (11) | −0.0007 (12) |
C9 | 0.0285 (13) | 0.0369 (14) | 0.0320 (14) | −0.0004 (10) | −0.0045 (12) | −0.0029 (13) |
C10 | 0.0391 (18) | 0.0520 (19) | 0.051 (2) | 0.0004 (14) | 0.0098 (15) | −0.0118 (16) |
C11 | 0.0320 (13) | 0.0386 (14) | 0.0283 (14) | −0.0022 (11) | 0.0004 (11) | −0.0007 (12) |
C12 | 0.0375 (15) | 0.0390 (15) | 0.0433 (18) | −0.0030 (12) | −0.0069 (14) | 0.0004 (14) |
C13 | 0.0493 (18) | 0.0417 (16) | 0.051 (2) | −0.0117 (14) | −0.0067 (16) | −0.0053 (16) |
C14 | 0.061 (2) | 0.0300 (14) | 0.049 (2) | −0.0025 (14) | 0.0047 (16) | −0.0004 (13) |
C15 | 0.0499 (19) | 0.0404 (16) | 0.0487 (19) | 0.0091 (14) | −0.0037 (16) | 0.0025 (15) |
C16 | 0.0379 (15) | 0.0398 (15) | 0.0439 (18) | 0.0005 (12) | −0.0069 (14) | −0.0015 (14) |
S1—O1 | 1.428 (2) | C5—H5 | 0.9300 |
S1—O2 | 1.435 (2) | C6—C7 | 1.464 (4) |
S1—N1 | 1.651 (3) | C7—C8 | 1.395 (4) |
S1—C1 | 1.770 (3) | C8—C9 | 1.390 (4) |
N1—C8 | 1.436 (3) | C9—C11 | 1.462 (4) |
N1—C10 | 1.483 (4) | C10—H10A | 0.9600 |
N2—N3 | 1.348 (3) | C10—H10B | 0.9600 |
N2—C9 | 1.356 (3) | C10—H10C | 0.9600 |
N2—H2N | 0.8600 | C11—C16 | 1.388 (4) |
N3—C7 | 1.342 (3) | C11—C12 | 1.398 (4) |
C1—C2 | 1.391 (4) | C12—C13 | 1.390 (4) |
C1—C6 | 1.406 (4) | C12—H12 | 0.9300 |
C2—C3 | 1.377 (5) | C13—C14 | 1.379 (5) |
C2—H2 | 0.9300 | C13—H13 | 0.9300 |
C3—C4 | 1.389 (5) | C14—C15 | 1.380 (5) |
C3—H3 | 0.9300 | C14—H14 | 0.9300 |
C4—C5 | 1.380 (4) | C15—C16 | 1.379 (4) |
C4—H4 | 0.9300 | C15—H15 | 0.9300 |
C5—C6 | 1.390 (4) | C16—H16 | 0.9300 |
O1—S1—O2 | 118.47 (16) | N3—C7—C6 | 124.3 (2) |
O1—S1—N1 | 108.48 (14) | C8—C7—C6 | 124.4 (2) |
O2—S1—N1 | 106.54 (13) | C9—C8—C7 | 106.7 (2) |
O1—S1—C1 | 110.17 (14) | C9—C8—N1 | 130.7 (2) |
O2—S1—C1 | 107.91 (14) | C7—C8—N1 | 122.5 (2) |
N1—S1—C1 | 104.31 (14) | N2—C9—C8 | 103.6 (2) |
C8—N1—C10 | 113.4 (3) | N2—C9—C11 | 123.1 (2) |
C8—N1—S1 | 110.27 (19) | C8—C9—C11 | 133.2 (2) |
C10—N1—S1 | 115.5 (2) | N1—C10—H10A | 109.5 |
N3—N2—C9 | 115.1 (2) | N1—C10—H10B | 109.5 |
N3—N2—H2N | 122.5 | H10A—C10—H10B | 109.5 |
C9—N2—H2N | 122.5 | N1—C10—H10C | 109.5 |
C7—N3—N2 | 103.4 (2) | H10A—C10—H10C | 109.5 |
C2—C1—C6 | 121.3 (3) | H10B—C10—H10C | 109.5 |
C2—C1—S1 | 120.3 (2) | C16—C11—C12 | 118.6 (3) |
C6—C1—S1 | 118.3 (2) | C16—C11—C9 | 120.6 (3) |
C3—C2—C1 | 118.8 (3) | C12—C11—C9 | 120.7 (3) |
C3—C2—H2 | 120.6 | C13—C12—C11 | 119.9 (3) |
C1—C2—H2 | 120.6 | C13—C12—H12 | 120.0 |
C2—C3—C4 | 120.7 (3) | C11—C12—H12 | 120.0 |
C2—C3—H3 | 119.6 | C14—C13—C12 | 120.7 (3) |
C4—C3—H3 | 119.6 | C14—C13—H13 | 119.6 |
C5—C4—C3 | 120.4 (3) | C12—C13—H13 | 119.6 |
C5—C4—H4 | 119.8 | C15—C14—C13 | 119.4 (3) |
C3—C4—H4 | 119.8 | C15—C14—H14 | 120.3 |
C4—C5—C6 | 120.3 (3) | C13—C14—H14 | 120.3 |
C4—C5—H5 | 119.9 | C16—C15—C14 | 120.4 (3) |
C6—C5—H5 | 119.9 | C16—C15—H15 | 119.8 |
C5—C6—C1 | 118.4 (3) | C14—C15—H15 | 119.8 |
C5—C6—C7 | 123.8 (3) | C15—C16—C11 | 120.9 (3) |
C1—C6—C7 | 117.8 (3) | C15—C16—H16 | 119.5 |
N3—C7—C8 | 111.2 (2) | C11—C16—H16 | 119.5 |
O1—S1—N1—C8 | 168.8 (2) | C5—C6—C7—C8 | −163.6 (3) |
O2—S1—N1—C8 | −62.7 (2) | C1—C6—C7—C8 | 15.2 (4) |
C1—S1—N1—C8 | 51.3 (2) | N3—C7—C8—C9 | 0.0 (4) |
O1—S1—N1—C10 | 38.5 (3) | C6—C7—C8—C9 | −177.8 (3) |
O2—S1—N1—C10 | 167.1 (2) | N3—C7—C8—N1 | −177.3 (3) |
C1—S1—N1—C10 | −78.9 (2) | C6—C7—C8—N1 | 4.9 (5) |
C9—N2—N3—C7 | −0.3 (4) | C10—N1—C8—C9 | −86.5 (4) |
O1—S1—C1—C2 | 30.8 (3) | S1—N1—C8—C9 | 142.1 (3) |
O2—S1—C1—C2 | −99.9 (3) | C10—N1—C8—C7 | 90.0 (3) |
N1—S1—C1—C2 | 147.0 (2) | S1—N1—C8—C7 | −41.3 (4) |
O1—S1—C1—C6 | −152.0 (2) | N3—N2—C9—C8 | 0.3 (4) |
O2—S1—C1—C6 | 77.3 (3) | N3—N2—C9—C11 | −177.4 (3) |
N1—S1—C1—C6 | −35.8 (3) | C7—C8—C9—N2 | −0.2 (3) |
C6—C1—C2—C3 | −0.9 (5) | N1—C8—C9—N2 | 176.8 (3) |
S1—C1—C2—C3 | 176.2 (3) | C7—C8—C9—C11 | 177.2 (3) |
C1—C2—C3—C4 | 0.4 (5) | N1—C8—C9—C11 | −5.8 (6) |
C2—C3—C4—C5 | 1.0 (6) | N2—C9—C11—C16 | 162.7 (3) |
C3—C4—C5—C6 | −1.7 (5) | C8—C9—C11—C16 | −14.3 (5) |
C4—C5—C6—C1 | 1.1 (5) | N2—C9—C11—C12 | −14.2 (5) |
C4—C5—C6—C7 | 179.8 (3) | C8—C9—C11—C12 | 168.7 (3) |
C2—C1—C6—C5 | 0.2 (4) | C16—C11—C12—C13 | 0.1 (5) |
S1—C1—C6—C5 | −176.9 (2) | C9—C11—C12—C13 | 177.2 (3) |
C2—C1—C6—C7 | −178.6 (3) | C11—C12—C13—C14 | −0.3 (6) |
S1—C1—C6—C7 | 4.2 (4) | C12—C13—C14—C15 | 0.2 (6) |
N2—N3—C7—C8 | 0.2 (3) | C13—C14—C15—C16 | −0.1 (6) |
N2—N3—C7—C6 | 178.0 (3) | C14—C15—C16—C11 | 0.0 (5) |
C5—C6—C7—N3 | 18.9 (5) | C12—C11—C16—C15 | 0.0 (5) |
C1—C6—C7—N3 | −162.4 (3) | C9—C11—C16—C15 | −177.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O2i | 0.86 | 2.12 | 2.912 (3) | 152 |
C3—H3···N3ii | 0.93 | 2.56 | 3.429 (4) | 155 |
C10—H10C···O1 | 0.96 | 2.49 | 2.883 (4) | 104 |
C16—H16···N1 | 0.93 | 2.62 | 3.263 (4) | 127 |
Symmetry codes: (i) −x+2, −y, z+1/2; (ii) x−1/2, −y−1/2, z. |
Experimental details
Crystal data | |
Chemical formula | C16H13N3O2S |
Mr | 311.35 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 295 |
a, b, c (Å) | 12.1028 (5), 16.3934 (7), 7.0962 (3) |
V (Å3) | 1407.93 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.20 × 0.10 × 0.06 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1997) |
Tmin, Tmax | 0.953, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8451, 3037, 2798 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.112, 1.08 |
No. of reflections | 3037 |
No. of parameters | 201 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.24 |
Absolute structure | Racemic twin; used 1306 unmerged Friedel pairs (Flack, 1983) |
Absolute structure parameter | 0.53 (11) |
Computer programs: COLLECT (Nonius, 1999), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O2i | 0.86 | 2.12 | 2.912 (3) | 152.4 |
C3—H3···N3ii | 0.93 | 2.56 | 3.429 (4) | 155.1 |
C16—H16···N1 | 0.93 | 2.62 | 3.263 (4) | 126.7 |
Symmetry codes: (i) −x+2, −y, z+1/2; (ii) x−1/2, −y−1/2, z. |
Footnotes
†This paper is dedicated to Dr Hamid Latif Siddiqui who passed away to heaven on July 26, 2012.
Acknowledgements
The authors are grateful to the Higher Education Commission, Pakistan, and Institute of Chemistry, University of the Punjab, Lahore, Pakistan, for financial support.
References
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Among the broad class of heterocyclic compounds, pyrazole and benzothiazine nuclei are well known for their biological activity potential. Oxicam drugs are benzothiazine based potent anti-inflammatory and analgesic drugs (Turck et al. 1996; Lombardino et al., 1973; Zinnes et al., 1973), whereas celecoxib, an anti-inflammatory drug and selective inhibitor of cox-2 enzyme, contains pyrazole fragment (Silverstein et al., 2000). Keeping in view these facts and figures, we have prepared some pyrazolobenzothiazines which contain both of these medicinally important heterocycles fused with eachother (Ahmad et al., 2010a & b). We report here the crystal structure of the title compound.
The bond distances and angles in the title compound (Fig. 1) agree very well with the corresponding bond distances and angles observed in closely related structures (Siddiqui et al., 2008; 2009). The heterocyclic thiazine ring adopts a twist chair conformation with atoms S1 and C1 displaced by 0.946 (5) and 0.405 (6) Å, respectively, on the same side from the mean plane formed by the remaining ring atoms (N1/C6–C8). The mean planes of the benzene rings C1–C6 and C11–C16 make dihedral angles 16.61 (10) and 15.32 (10)°, respectively, with the mean-plane of the pyrazole ring (N2/N3/C7/C8/C10).
The molecular structure of the title compound is consolidated by intramolecular interactions C10—H10C···O1 and C16—H16···N1. The crystal structure is stabilized by intermolecular hydrogen bonding interactions N2—H2N···O2 and C3—H3···N3 (Fig. 2 and Table 1).