4-Methyl-3-phenyl-2,4-dihydro-pyrazolo-[4,3-c][1,2]benzothia-zine 5,5-dioxide.

In the title mol-ecule, C(16)H(13)N(3)O(2)S, the heterocyclic thia-zine 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 mol-ecular structure is consolidated by intra-molecular C-H⋯N inter-actions and the crystal packing is stabilized by N-H⋯O and C-H⋯N hydrogen bonds. The crystal studied was an inversion twin 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

C16H13N3O2S

M = 311.35

Orthorhombic,

a = 12.1028 (5) Å

b = 16.3934 (7) Å

c = 7.0962 (3) Å

V = 1407.93 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 295 K

0.20 × 0.10 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.953, T max = 0.986

8451 measured reflections

3037 independent reflections

2798 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.112

S = 1.08

3037 reflections

201 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: inversion twin; used 1306 unmerged Friedel pairs (Flack, 1983 ▶)

Flack parameter: 0.53 (11)

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812033284/yk2066sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033284/yk2066Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033284/yk2066Isup3.cml

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

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	Flack parameter: 0.53 (11)

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

Table 1

Hydrogen-bond geometry (Å, °)

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
C16—H16⋯N1	0.93	2.62	3.263 (4)	127

Symmetry codes: (i) ; (ii) .