3,4-Dimethyl-2-(2-oxo-2-phenyl­eth­yl)-2H,4H-pyrazolo­[4,3-c][1,2]benzothia­zine-5,5-dione

Aslam, S.; Siddiqui, H.L.; Ahmad, M.; Bukhari, I.H.; Parvez, M.

doi:10.1107/S1600536812002188

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o502

doi:10.1107/S1600536812002188

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3,4-Dimethyl-2-(2-oxo-2-phenylethyl)-2H,4H-pyrazolo[4,3-c][1,2]benzothiazine-5,5-dione

Sana Aslam,^a Hamid Latif Siddiqui,^a ^* Matloob Ahmad,^b Iftikhar Hussain Bukhari ^b and Masood Parvez ^c

^aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, ^bChemistry Department, Govt. College University, Faisalabad, Pakistan, and ^cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: drhamidlatif@yahoo.com

(Received 7 January 2012; accepted 18 January 2012; online 21 January 2012)

In the title molecule, C₁₉H₁₇N₃O₃S, the heterocyclic thiazine 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 intermolecular C—H⋯O hydrogen-bonding interactions 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_r = 367.42
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.069
wR(F²) = 0.146
S = 1.15
3970 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.44 e Å⁻³

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) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+1, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812002188/pk2383sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812002188/pk2383Isup3.cml

checkCIF report

Comment top

Both benzothiazines and pyrazoles are known as versatile biologically active heterocyclic nuclei. Pyrazoles are found to be cytotoxic agents (Ciciani et al., 2008), anti-tumor (Farag et al., 2008), anti-malarial (Cunico et al., 2006), etc. In continuation of our research interests in biologically active molecules (Ahmad et al., 2010), we have fused both of these heterocycles and herein report the synthesis and crystal structure of the title compound.

The bond distances and angles in the title molecule (Fig. 1) agree very well with the corresponding bond distances and angles reported in closely related compounds (Siddiqui et al., 2008). The heterocyclic thiazine ring adopts a half chair conformation with atoms S1 and N1 displaced by 0.530 (5) and 0.229 (6) Å, respectively, on opposite sides from the mean plane formed by the remaining ring atoms. The ethanone group O3/C12/C13/C14 is oriented at 3.8 (3) °, with the benzene ring (C14–C19) which lies almost perpendicular to the pyrazolyl ring (N2/N3/C7/C8/C10) with a dihedral between the two planes of 89.22 (11)°. The structure is devoid of classical hydrogen bonds. However, intermolecular hydrogen bonding interactions of C—H···O type are present (Table 1).

Related literature top

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 top

Equimolar quantities of 3,4-dimethyl-2,4-dihydropyrazolo[4,3-c][1,2] benzothiazine 5,5-dioxide (1.0 g, 4.01 mmol) and corresponding phenacyl bromide (0.80 g, 4.01 mmol) were dissolved in acetonitrile (20 ml) followed by the addition of equimolar K₂CO₃ (0.55 g, 4.01 mmol). The mixture was subjected to reflux for 7 h. The completion of reaction was monitored with the help of TLC. The precipitates of the title compound were collected and washed with methanol. The crystals suitable for X-ray crystallographic analysis were grown from a solution of CHCl₃:MeOH in 1:1 ratio.

Computing details top

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 (Sheldrick, 2008).

Figures top

	Fig. 1. The title molecule with displacement ellipsoids plotted at the 30% probability level.
	Fig. 2. A part of the unit cell showing intermolecular hydrogen bonding interactions as dashed lines. H-atoms not involved in hydrogen bonding have been excluded for clarity.

3,4-Dimethyl-2-(2-oxo-2-phenylethyl)-2H,4H- pyrazolo[4,3-c][1,2]benzothiazine-5,5-dione top

Crystal data top

C₁₉H₁₇N₃O₃S	F(000) = 1536
M_r = 367.42	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.025P)² + 10.0879P] where P = (F_o² + 2F_c²)/3
3970 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₉H₁₇N₃O₃S	V = 3500.1 (19) Å³
M_r = 367.42	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.380 (6) Å	µ = 0.21 mm⁻¹
b = 11.141 (4) Å	T = 200 K
c = 14.996 (5) Å	0.12 × 0.10 × 0.08 mm
β = 120.76 (2)°

Data collection top

Nonius KappaCCD diffractometer	3970 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	2847 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.983	R_int = 0.073
12615 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.025P)² + 10.0879P] where P = (F_o² + 2F_c²)/3
3970 reflections	Δρ_max = 0.27 e Å⁻³
237 parameters	Δρ_min = −0.44 e Å⁻³

Special details top

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) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y−1/2, −z+1/2; (ii) −x+1, y, −z+1/2; (iii) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇N₃O₃S
M_r	367.42
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	200
a, b, c (Å)	24.380 (6), 11.141 (4), 14.996 (5)
β (°)	120.76 (2)
V (Å³)	3500.1 (19)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.975, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	12615, 3970, 2847
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.146, 1.15
No. of reflections	3970
No. of parameters	237
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.025P)² + 10.0879P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.44

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

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)	162.8
C11—H11C···O1ⁱⁱⁱ	0.98	2.44	3.406 (4)	167.9

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

Acknowledgements

The authors are grateful to the Higher Education Commission, Pakistan, and the Institute of Chemistry, University of the Punjab, Lahore, Pakistan, for financial support.

References

Ahmad, M., Siddiqui, H. L., Zia-ur-Rehman, M. & Parvez, M. (2010). Eur. J. Med. Chem. 45, 698–704. Web of Science CSD CrossRef PubMed CAS Google Scholar
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421–426. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ciciani, G., Coronnello, M., Guerrini, G., Selleri, S., Cantore, M., Failli, P., Mini, E. & Costanzo, A. (2008). Bioorg. Med. Chem. 16, 9409–9419. Web of Science CrossRef PubMed CAS Google Scholar
Cunico, W., Cechinel, C. A., Bonacorso, H. G., Martins, M. A. P., Zanatta, N., Souza, M. V. N., Freitas, I. O., Soaresa, R. P. & Krettli, A. U. (2006). Bioorg. Med. Chem. 16, 649–653. CrossRef CAS Google Scholar
Farag, A. M., Mayhoub, A. S., Barakatb, S. E. & Bayomi, A. H. (2008). Bioorg. Med. Chem. Lett. 16, 881–889. CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siddiqui, W. A., Ahmad, S., Tariq, M. I., Siddiqui, H. L. & Parvez, M. (2008). Acta Cryst. C64, o4–o6. Web of Science CSD CrossRef IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3,4-Di­methyl-2-(2-oxo-2-phenyl­eth­yl)-2H,4H-pyrazolo­[4,3-c][1,2]benzo­thia­zine-5,5-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,4-Dimethyl-2-(2-oxo-2-phenylethyl)-2H,4H-pyrazolo[4,3-c][1,2]benzothiazine-5,5-dione