3,4-Dimethyl-2-(2-oxo-2-phenyl-eth-yl)-2H,4H-pyrazolo-[4,3-c][1,2]benzothia-zine-5,5-dione.

In the title mol-ecule, C(19)H(17)N(3)O(3)S, the heterocyclic thia-zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.530 (5) and 0.229 (6) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The ethanone group lies at an angle of 3.8 (3)° with respect to the benzene ring, which lies almost perendicular to the pyrazole ring, with a dihedral between the two planes of 89.22 (11)°. Weak inter-molecular C-H⋯O hydrogen-bonding inter-actions are present.

Related literature

For the biological activity of pyrazoles, see: Farag et al. (2008 ▶); Ciciani et al. (2008 ▶); Cunico et al. (2006 ▶); Ahmad et al. (2010 ▶). For related structures, see: Siddiqui et al. (2008 ▶).

Experimental

Crystal data

C19H17N3O3S

M = 367.42

Monoclinic,

a = 24.380 (6) Å

b = 11.141 (4) Å

c = 14.996 (5) Å

β = 120.76 (2)°

V = 3500.1 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 200 K

0.12 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.975, T max = 0.983

12615 measured reflections

3970 independent reflections

2847 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.146

S = 1.15

3970 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.44 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); 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/S1600536812002188/pk2383sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002188/pk2383Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002188/pk2383Isup3.cml

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

C19H17N3O3S	F(000) = 1536
Mr = 367.42	Dx = 1.394 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6235 reflections
a = 24.380 (6) Å	θ = 1.0–27.5°
b = 11.141 (4) Å	µ = 0.21 mm−1
c = 14.996 (5) Å	T = 200 K
β = 120.76 (2)°	Block, colorless
V = 3500.1 (19) Å3	0.12 × 0.10 × 0.08 mm
Z = 8

Nonius KappaCCD diffractometer	3970 independent reflections
Radiation source: fine-focus sealed tube	2847 reflections with I > 2σ(I)
graphite	Rint = 0.073
ω and φ scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −31→30
Tmin = 0.975, Tmax = 0.983	k = −14→14
12615 measured reflections	l = −18→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.025P)2 + 10.0879P] where P = (Fo2 + 2Fc2)/3
3970 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.37478 (4)	0.35736 (7)	0.23368 (6)	0.0377 (2)
O1	0.41198 (11)	0.3575 (2)	0.18465 (19)	0.0511 (6)
O2	0.33464 (11)	0.4586 (2)	0.21844 (19)	0.0470 (6)
O3	0.42366 (12)	0.1146 (2)	0.65556 (19)	0.0555 (7)
N1	0.42423 (11)	0.3433 (2)	0.3603 (2)	0.0348 (6)
N2	0.31406 (11)	0.2240 (2)	0.43305 (19)	0.0333 (6)
N3	0.35687 (12)	0.2864 (2)	0.51876 (19)	0.0337 (6)
C1	0.26868 (14)	0.0818 (3)	0.2346 (2)	0.0356 (7)
H1	0.2551	0.0498	0.2788	0.043*
C2	0.24943 (16)	0.0283 (3)	0.1398 (3)	0.0445 (8)
H2	0.2219	−0.0394	0.1190	0.053*
C3	0.26953 (17)	0.0715 (3)	0.0750 (3)	0.0496 (9)
H3	0.2563	0.0329	0.0106	0.059*
C4	0.30886 (17)	0.1711 (3)	0.1036 (3)	0.0447 (8)
H4	0.3230	0.2010	0.0595	0.054*
C5	0.32727 (14)	0.2264 (3)	0.1974 (2)	0.0347 (7)
C6	0.30809 (13)	0.1828 (3)	0.2652 (2)	0.0311 (6)
C7	0.33508 (13)	0.2388 (3)	0.3667 (2)	0.0304 (6)
C8	0.39001 (14)	0.3110 (3)	0.4110 (2)	0.0320 (6)
C9	0.48457 (15)	0.2765 (3)	0.3945 (3)	0.0445 (8)
H9A	0.5120	0.2825	0.4701	0.067*
H9B	0.5067	0.3109	0.3614	0.067*
H9C	0.4748	0.1919	0.3747	0.067*
C10	0.40399 (14)	0.3389 (3)	0.5091 (2)	0.0354 (7)
C11	0.45835 (17)	0.4063 (3)	0.5944 (3)	0.0501 (9)
H11A	0.4820	0.4479	0.5668	0.075*
H11B	0.4869	0.3501	0.6487	0.075*
H11C	0.4420	0.4651	0.6236	0.075*
C12	0.35231 (15)	0.2791 (3)	0.6109 (2)	0.0365 (7)
H12A	0.3071	0.2675	0.5907	0.044*
H12B	0.3673	0.3555	0.6499	0.044*
C13	0.39244 (14)	0.1753 (3)	0.6804 (2)	0.0351 (7)
C14	0.39025 (14)	0.1515 (3)	0.7764 (2)	0.0345 (7)
C15	0.35436 (16)	0.2220 (3)	0.8039 (2)	0.0432 (8)
H15	0.3320	0.2899	0.7632	0.052*
C16	0.35119 (18)	0.1929 (4)	0.8912 (3)	0.0551 (10)
H16	0.3268	0.2414	0.9102	0.066*
C17	0.38329 (16)	0.0941 (3)	0.9503 (3)	0.0442 (8)
H17	0.3802	0.0735	1.0091	0.053*
C18	0.41977 (15)	0.0256 (3)	0.9241 (2)	0.0389 (7)
H18	0.4425	−0.0417	0.9656	0.047*
C19	0.42368 (15)	0.0537 (3)	0.8375 (2)	0.0378 (7)
H19	0.4492	0.0063	0.8200	0.045*

	U11	U22	U33	U12	U13	U23
S1	0.0417 (4)	0.0377 (4)	0.0452 (5)	0.0021 (4)	0.0305 (4)	0.0067 (4)
O1	0.0548 (15)	0.0607 (16)	0.0576 (15)	0.0012 (13)	0.0430 (13)	0.0104 (13)
O2	0.0550 (15)	0.0386 (13)	0.0570 (15)	0.0097 (11)	0.0356 (13)	0.0128 (12)
O3	0.0629 (16)	0.0654 (18)	0.0503 (15)	0.0271 (14)	0.0377 (13)	0.0125 (13)
N1	0.0318 (13)	0.0371 (15)	0.0427 (15)	−0.0028 (11)	0.0243 (12)	0.0012 (12)
N2	0.0305 (13)	0.0380 (14)	0.0324 (13)	0.0011 (11)	0.0169 (11)	0.0020 (11)
N3	0.0353 (13)	0.0373 (14)	0.0313 (13)	0.0017 (12)	0.0190 (11)	0.0019 (11)
C1	0.0288 (15)	0.0397 (18)	0.0354 (17)	0.0004 (14)	0.0144 (14)	0.0027 (14)
C2	0.0388 (18)	0.0427 (19)	0.0447 (19)	−0.0034 (15)	0.0160 (16)	−0.0040 (16)
C3	0.054 (2)	0.053 (2)	0.0355 (18)	0.0026 (18)	0.0183 (17)	−0.0076 (17)
C4	0.053 (2)	0.050 (2)	0.0370 (18)	0.0111 (17)	0.0275 (17)	0.0050 (16)
C5	0.0332 (16)	0.0378 (17)	0.0358 (16)	0.0070 (14)	0.0196 (14)	0.0080 (14)
C6	0.0265 (14)	0.0351 (16)	0.0311 (16)	0.0044 (12)	0.0143 (12)	0.0051 (13)
C7	0.0276 (14)	0.0348 (16)	0.0315 (15)	0.0022 (13)	0.0171 (13)	0.0034 (13)
C8	0.0322 (15)	0.0333 (16)	0.0350 (16)	−0.0010 (13)	0.0204 (13)	0.0001 (13)
C9	0.0341 (17)	0.047 (2)	0.059 (2)	0.0022 (16)	0.0292 (17)	0.0043 (18)
C10	0.0341 (16)	0.0352 (17)	0.0391 (17)	0.0011 (14)	0.0203 (14)	0.0011 (14)
C11	0.046 (2)	0.054 (2)	0.050 (2)	−0.0121 (18)	0.0240 (18)	−0.0155 (18)
C12	0.0428 (17)	0.0383 (17)	0.0343 (16)	0.0014 (15)	0.0241 (15)	−0.0009 (14)
C13	0.0324 (15)	0.0393 (17)	0.0348 (16)	0.0031 (14)	0.0179 (14)	−0.0005 (14)
C14	0.0312 (15)	0.0403 (17)	0.0320 (16)	−0.0004 (14)	0.0162 (13)	0.0009 (14)
C15	0.0458 (19)	0.050 (2)	0.0403 (18)	0.0174 (17)	0.0265 (16)	0.0124 (16)
C16	0.058 (2)	0.070 (3)	0.049 (2)	0.025 (2)	0.036 (2)	0.015 (2)
C17	0.0404 (18)	0.057 (2)	0.0380 (18)	0.0040 (17)	0.0223 (16)	0.0093 (17)
C18	0.0358 (16)	0.0367 (17)	0.0371 (17)	0.0002 (14)	0.0136 (14)	0.0045 (14)
C19	0.0362 (17)	0.0367 (18)	0.0411 (18)	0.0059 (14)	0.0202 (15)	0.0002 (14)

S1—O1	1.430 (2)	C8—C10	1.365 (4)
S1—O2	1.433 (2)	C9—H9A	0.9800
S1—N1	1.656 (3)	C9—H9B	0.9800
S1—C5	1.766 (3)	C9—H9C	0.9800
O3—C13	1.211 (4)	C10—C11	1.490 (4)
N1—C8	1.432 (3)	C11—H11A	0.9800
N1—C9	1.486 (4)	C11—H11B	0.9800
N2—C7	1.342 (3)	C11—H11C	0.9800
N2—N3	1.361 (3)	C12—C13	1.530 (4)
N3—C10	1.362 (4)	C12—H12A	0.9900
N3—C12	1.444 (4)	C12—H12B	0.9900
C1—C2	1.383 (4)	C13—C14	1.491 (4)
C1—C6	1.396 (4)	C14—C15	1.386 (4)
C1—H1	0.9500	C14—C19	1.387 (4)
C2—C3	1.381 (5)	C15—C16	1.388 (4)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.383 (5)	C16—C17	1.378 (5)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.383 (4)	C17—C18	1.374 (4)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.406 (4)	C18—C19	1.386 (4)
C6—C7	1.454 (4)	C18—H18	0.9500
C7—C8	1.404 (4)	C19—H19	0.9500
O1—S1—O2	118.56 (15)	N1—C9—H9C	109.5
O1—S1—N1	107.98 (14)	H9A—C9—H9C	109.5
O2—S1—N1	107.12 (14)	H9B—C9—H9C	109.5
O1—S1—C5	109.31 (15)	N3—C10—C8	104.9 (3)
O2—S1—C5	108.32 (14)	N3—C10—C11	123.6 (3)
N1—S1—C5	104.67 (14)	C8—C10—C11	131.4 (3)
C8—N1—C9	115.7 (3)	C10—C11—H11A	109.5
C8—N1—S1	110.62 (19)	C10—C11—H11B	109.5
C9—N1—S1	117.0 (2)	H11A—C11—H11B	109.5
C7—N2—N3	103.8 (2)	C10—C11—H11C	109.5
N2—N3—C10	113.6 (2)	H11A—C11—H11C	109.5
N2—N3—C12	118.5 (2)	H11B—C11—H11C	109.5
C10—N3—C12	127.5 (3)	N3—C12—C13	111.0 (2)
C2—C1—C6	120.0 (3)	N3—C12—H12A	109.4
C2—C1—H1	120.0	C13—C12—H12A	109.4
C6—C1—H1	120.0	N3—C12—H12B	109.4
C3—C2—C1	121.1 (3)	C13—C12—H12B	109.4
C3—C2—H2	119.4	H12A—C12—H12B	108.0
C1—C2—H2	119.4	O3—C13—C14	122.5 (3)
C2—C3—C4	120.0 (3)	O3—C13—C12	119.7 (3)
C2—C3—H3	120.0	C14—C13—C12	117.8 (3)
C4—C3—H3	120.0	C15—C14—C19	119.7 (3)
C3—C4—C5	119.1 (3)	C15—C14—C13	121.7 (3)
C3—C4—H4	120.4	C19—C14—C13	118.6 (3)
C5—C4—H4	120.4	C14—C15—C16	119.8 (3)
C4—C5—C6	121.7 (3)	C14—C15—H15	120.1
C4—C5—S1	120.1 (2)	C16—C15—H15	120.1
C6—C5—S1	118.1 (2)	C17—C16—C15	120.4 (3)
C1—C6—C5	117.9 (3)	C17—C16—H16	119.8
C1—C6—C7	123.9 (3)	C15—C16—H16	119.8
C5—C6—C7	118.0 (3)	C18—C17—C16	119.8 (3)
N2—C7—C8	110.7 (3)	C18—C17—H17	120.1
N2—C7—C6	125.7 (3)	C16—C17—H17	120.1
C8—C7—C6	123.5 (3)	C17—C18—C19	120.5 (3)
C10—C8—C7	107.0 (3)	C17—C18—H18	119.8
C10—C8—N1	128.5 (3)	C19—C18—H18	119.8
C7—C8—N1	124.5 (3)	C18—C19—C14	119.8 (3)
N1—C9—H9A	109.5	C18—C19—H19	120.1
N1—C9—H9B	109.5	C14—C19—H19	120.1
H9A—C9—H9B	109.5
O1—S1—N1—C8	−164.8 (2)	C6—C7—C8—C10	−174.9 (3)
O2—S1—N1—C8	66.5 (2)	N2—C7—C8—N1	179.7 (3)
C5—S1—N1—C8	−48.4 (2)	C6—C7—C8—N1	3.3 (5)
O1—S1—N1—C9	−29.4 (3)	C9—N1—C8—C10	74.8 (4)
O2—S1—N1—C9	−158.1 (2)	S1—N1—C8—C10	−149.2 (3)
C5—S1—N1—C9	87.0 (2)	C9—N1—C8—C7	−103.0 (4)
C7—N2—N3—C10	−0.4 (3)	S1—N1—C8—C7	33.0 (4)
C7—N2—N3—C12	−173.6 (3)	N2—N3—C10—C8	1.3 (3)
C6—C1—C2—C3	1.3 (5)	C12—N3—C10—C8	173.8 (3)
C1—C2—C3—C4	−0.9 (5)	N2—N3—C10—C11	−176.5 (3)
C2—C3—C4—C5	−0.3 (5)	C12—N3—C10—C11	−4.0 (5)
C3—C4—C5—C6	1.3 (5)	C7—C8—C10—N3	−1.6 (3)
C3—C4—C5—S1	−177.4 (3)	N1—C8—C10—N3	−179.7 (3)
O1—S1—C5—C4	−27.1 (3)	C7—C8—C10—C11	176.0 (3)
O2—S1—C5—C4	103.5 (3)	N1—C8—C10—C11	−2.2 (6)
N1—S1—C5—C4	−142.5 (3)	N2—N3—C12—C13	90.0 (3)
O1—S1—C5—C6	154.2 (2)	C10—N3—C12—C13	−82.2 (4)
O2—S1—C5—C6	−75.3 (3)	N3—C12—C13—O3	1.9 (4)
N1—S1—C5—C6	38.8 (3)	N3—C12—C13—C14	−176.9 (3)
C2—C1—C6—C5	−0.3 (4)	O3—C13—C14—C15	179.8 (3)
C2—C1—C6—C7	−174.6 (3)	C12—C13—C14—C15	−1.4 (5)
C4—C5—C6—C1	−0.9 (4)	O3—C13—C14—C19	−2.1 (5)
S1—C5—C6—C1	177.8 (2)	C12—C13—C14—C19	176.6 (3)
C4—C5—C6—C7	173.6 (3)	C19—C14—C15—C16	−1.2 (5)
S1—C5—C6—C7	−7.7 (4)	C13—C14—C15—C16	176.8 (3)
N3—N2—C7—C8	−0.7 (3)	C14—C15—C16—C17	−0.3 (6)
N3—N2—C7—C6	175.7 (3)	C15—C16—C17—C18	1.4 (6)
C1—C6—C7—N2	−18.5 (5)	C16—C17—C18—C19	−1.1 (5)
C5—C6—C7—N2	167.3 (3)	C17—C18—C19—C14	−0.4 (5)
C1—C6—C7—C8	157.4 (3)	C15—C14—C19—C18	1.5 (5)
C5—C6—C7—C8	−16.8 (4)	C13—C14—C19—C18	−176.6 (3)
N2—C7—C8—C10	1.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2i	0.95	2.43	3.246 (5)	144
C9—H9B···O1ii	0.98	2.46	3.413 (4)	163.
C11—H11C···O1iii	0.98	2.44	3.406 (4)	168.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2i	0.95	2.43	3.246 (5)	144
C9—H9B⋯O1ii	0.98	2.46	3.413 (4)	163
C11—H11C⋯O1iii	0.98	2.44	3.406 (4)	168

Symmetry codes: (i) ; (ii) ; (iii) .