2-(3,4-Dimethyl-5,5-dioxo-2H,4H-pyrazolo­[4,3-c][1,2]benzothia­zin-2-yl)-1-(4-meth­oxy­phen­yl)ethanone

Aslam, S.; Siddiqui, H.L.; Ahmad, M.; Hussain, T.; Parvez, M.

doi:10.1107/S1600536812001286

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o458-o459

doi:10.1107/S1600536812001286

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2-(3,4-Dimethyl-5,5-dioxo-2H,4H-pyrazolo[4,3-c][1,2]benzothiazin-2-yl)-1-(4-methoxyphenyl)ethanone

Sana Aslam,^a Hamid Latif Siddiqui,^a ^* Matloob Ahmad,^b Tanvir Hussain ^a 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 29 December 2011; accepted 11 January 2012; online 18 January 2012)

In the title molecule, C₂₀H₁₉N₃O₄S, the heterocyclic thiazine ring adopts a half-chair conformation with the S and N atoms displaced by 0.492 (6) and 0.199 (6) Å, respectively, on opposite sides from the mean plane formed by the remaining ring atoms. The ethanone group lies at an angle of 9.4 (2)° with respect to the benzene ring, which lies almost perpendicular to the pyrazole ring, with a dihedral between the two planes of 78.07 (9)°. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds.

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 a related structure, see: Siddiqui et al. (2008 ).

Experimental

Crystal data

C₂₀H₁₉N₃O₄S
M_r = 397.44
Monoclinic, P 2₁ /n
a = 13.862 (5) Å
b = 8.079 (2) Å
c = 17.748 (7) Å
β = 108.372 (18)°
V = 1886.3 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.14 × 0.09 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.972, T_max = 0.986
7270 measured reflections
4221 independent reflections
3206 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.132
S = 1.15
4221 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1ⁱ	0.95	2.34	3.216 (3)	154
C4—H4⋯O4ⁱⁱ	0.95	2.53	3.435 (4)	159
C9—H9A⋯O3ⁱⁱⁱ	0.98	2.54	3.335 (4)	138
C11—H11C⋯O2^iv	0.98	2.56	3.498 (4)	161
C12—H12B⋯O2^iv	0.99	2.33	3.309 (4)	170
Symmetry codes: (i) x, y-1, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z.

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/S1600536812001286/lx2223sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001286/lx2223Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812001286/lx2223Isup3.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 to 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 compound (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 the atoms S1 and N1 displaced by 0.492 (5) and 0.199 (5) Å, respectively, on the opposite sides from the mean plane formed by the remaining ring atoms. The ethanone group O3/C12/C13/C14 is oriented at 9.4 (2)° with the benzene ring (C14–C19) which forms a dihedral angle 78.07 (9)° with the pyrazolyl ring (N2/N3/C7/C8/C10). The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds (see, 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 a related structure, 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 p–methoxyphenacyl bromide (0.92 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 formed 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 molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the C—-H···O hydrogen bonds (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen- bonding were omitted for clarity. [Symmetry codes: (i) x, y + 1, z; (ii) - x + 1/2, y + 1/2, - z + 1/2; (iii) - x + 3/2, y + 1/2, - z + 1/2; (iv) x - 1/2, y - 1/2, z + 1/2.]

2-(3,4-Dimethyl-5,5-dioxo-2H,4H-pyrazolo[4,3- c][1,2]benzothiazin-2-yl)-1-(4-methoxyphenyl)ethanone top

Crystal data top

C₂₀H₁₉N₃O₄S	F(000) = 832
M_r = 397.44	D_x = 1.399 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7270 reflections
a = 13.862 (5) Å	θ = 1.0–27.5°
b = 8.079 (2) Å	µ = 0.20 mm⁻¹
c = 17.748 (7) Å	T = 173 K
β = 108.372 (18)°	Block, colorless
V = 1886.3 (11) Å³	0.14 × 0.09 × 0.07 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	4221 independent reflections
Radiation source: fine-focus sealed tube	3206 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ω and ϕ scans	θ_max = 27.5°, θ_min = 2.8°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −17→17
T_min = 0.972, T_max = 0.986	k = −9→10
7270 measured reflections	l = −22→22

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)] = 0.063	Hydrogen site location: difference Fourier map
wR(F²) = 0.132	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0125P)² + 3.1849P] where P = (F_o² + 2F_c²)/3
4221 reflections	(Δ/σ)_max < 0.001
256 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₀H₁₉N₃O₄S	V = 1886.3 (11) Å³
M_r = 397.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.862 (5) Å	µ = 0.20 mm⁻¹
b = 8.079 (2) Å	T = 173 K
c = 17.748 (7) Å	0.14 × 0.09 × 0.07 mm
β = 108.372 (18)°

Data collection top

Nonius KappaCCD diffractometer	4221 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	3206 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.986	R_int = 0.046
7270 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.15	Δρ_max = 0.27 e Å⁻³
4221 reflections	Δρ_min = −0.34 e Å⁻³
256 parameters

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	0.74841 (6)	0.70621 (8)	−0.04740 (5)	0.02818 (18)
O1	0.80588 (18)	0.8557 (2)	−0.03966 (15)	0.0421 (6)
O2	0.65575 (16)	0.6908 (3)	−0.11268 (13)	0.0364 (5)
O3	0.69947 (17)	0.1379 (3)	0.20986 (14)	0.0450 (6)
O4	0.42507 (16)	−0.3992 (2)	0.30314 (12)	0.0328 (5)
N1	0.71869 (18)	0.6790 (3)	0.03472 (15)	0.0278 (5)
N2	0.68248 (17)	0.2335 (3)	0.02702 (14)	0.0249 (5)
N3	0.61920 (17)	0.2872 (3)	0.06695 (14)	0.0247 (5)
C1	0.8567 (2)	0.2439 (3)	−0.04096 (18)	0.0285 (6)
H1	0.8446	0.1375	−0.0230	0.034*
C2	0.9282 (2)	0.2633 (4)	−0.08003 (19)	0.0318 (7)
H2	0.9630	0.1689	−0.0903	0.038*
C3	0.9497 (2)	0.4180 (4)	−0.10439 (18)	0.0305 (7)
H3	0.9994	0.4292	−0.1306	0.037*
C4	0.8986 (2)	0.5564 (4)	−0.09057 (17)	0.0290 (6)
H4	0.9138	0.6633	−0.1061	0.035*
C5	0.8247 (2)	0.5358 (3)	−0.05350 (16)	0.0225 (6)
C6	0.8025 (2)	0.3805 (3)	−0.02802 (16)	0.0226 (6)
C7	0.7262 (2)	0.3726 (3)	0.01260 (16)	0.0222 (5)
C8	0.6893 (2)	0.5120 (3)	0.04242 (16)	0.0238 (6)
C9	0.7789 (3)	0.7683 (4)	0.1072 (2)	0.0394 (8)
H9A	0.7481	0.7517	0.1493	0.059*
H9B	0.7799	0.8867	0.0956	0.059*
H9C	0.8486	0.7255	0.1248	0.059*
C10	0.6204 (2)	0.4540 (3)	0.07777 (17)	0.0248 (6)
C11	0.5603 (2)	0.5422 (4)	0.12170 (19)	0.0353 (7)
H11A	0.5545	0.6594	0.1068	0.053*
H11B	0.5947	0.5319	0.1789	0.053*
H11C	0.4923	0.4932	0.1083	0.053*
C12	0.5584 (2)	0.1665 (4)	0.09241 (18)	0.0287 (6)
H12A	0.5394	0.0759	0.0529	0.034*
H12B	0.4949	0.2199	0.0943	0.034*
C13	0.6139 (2)	0.0936 (4)	0.17351 (17)	0.0266 (6)
C14	0.5596 (2)	−0.0342 (3)	0.20525 (16)	0.0235 (6)
C15	0.4571 (2)	−0.0723 (3)	0.16869 (17)	0.0259 (6)
H15	0.4197	−0.0147	0.1220	0.031*
C16	0.4092 (2)	−0.1932 (3)	0.19962 (17)	0.0260 (6)
H16	0.3393	−0.2170	0.1747	0.031*
C17	0.4642 (2)	−0.2790 (3)	0.26725 (16)	0.0248 (6)
C18	0.5671 (2)	−0.2441 (3)	0.30382 (17)	0.0276 (6)
H18	0.6048	−0.3039	0.3498	0.033*
C19	0.6139 (2)	−0.1229 (3)	0.27307 (17)	0.0257 (6)
H19	0.6838	−0.0993	0.2982	0.031*
C20	0.3188 (2)	−0.4360 (4)	0.2697 (2)	0.0394 (8)
H20A	0.2989	−0.5161	0.3035	0.059*
H20B	0.3057	−0.4829	0.2164	0.059*
H20C	0.2792	−0.3342	0.2662	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0339 (4)	0.0189 (3)	0.0368 (4)	0.0020 (3)	0.0185 (3)	0.0031 (3)
O1	0.0553 (15)	0.0190 (10)	0.0655 (17)	−0.0036 (10)	0.0381 (13)	0.0001 (10)
O2	0.0346 (12)	0.0403 (12)	0.0350 (12)	0.0117 (10)	0.0121 (10)	0.0103 (10)
O3	0.0344 (13)	0.0554 (15)	0.0397 (13)	−0.0191 (11)	0.0039 (10)	0.0091 (11)
O4	0.0365 (12)	0.0297 (11)	0.0334 (12)	−0.0089 (9)	0.0127 (10)	0.0030 (9)
N1	0.0366 (14)	0.0194 (11)	0.0333 (14)	−0.0045 (10)	0.0192 (11)	−0.0043 (10)
N2	0.0261 (12)	0.0233 (11)	0.0282 (13)	−0.0023 (9)	0.0128 (10)	0.0000 (9)
N3	0.0280 (12)	0.0231 (11)	0.0255 (12)	−0.0010 (9)	0.0120 (10)	0.0012 (9)
C1	0.0302 (15)	0.0218 (14)	0.0339 (16)	−0.0019 (11)	0.0106 (13)	−0.0032 (12)
C2	0.0284 (15)	0.0289 (15)	0.0399 (17)	0.0046 (12)	0.0133 (13)	−0.0059 (13)
C3	0.0276 (15)	0.0327 (15)	0.0354 (17)	−0.0001 (12)	0.0157 (13)	−0.0026 (13)
C4	0.0284 (15)	0.0294 (15)	0.0293 (15)	−0.0024 (12)	0.0092 (13)	0.0034 (12)
C5	0.0238 (14)	0.0204 (13)	0.0243 (14)	0.0013 (10)	0.0088 (11)	−0.0010 (10)
C6	0.0228 (13)	0.0207 (13)	0.0242 (14)	−0.0026 (10)	0.0073 (11)	−0.0028 (10)
C7	0.0245 (14)	0.0203 (13)	0.0221 (13)	−0.0030 (10)	0.0078 (11)	−0.0008 (10)
C8	0.0269 (14)	0.0193 (13)	0.0247 (14)	−0.0009 (11)	0.0075 (12)	−0.0006 (10)
C9	0.047 (2)	0.0304 (16)	0.0435 (19)	−0.0080 (14)	0.0187 (16)	−0.0124 (14)
C10	0.0248 (14)	0.0254 (13)	0.0240 (14)	0.0004 (11)	0.0075 (12)	−0.0017 (11)
C11	0.0389 (18)	0.0334 (16)	0.0387 (18)	−0.0004 (13)	0.0197 (15)	−0.0057 (14)
C12	0.0277 (15)	0.0262 (14)	0.0339 (16)	−0.0051 (12)	0.0122 (13)	0.0029 (12)
C13	0.0248 (15)	0.0292 (14)	0.0273 (15)	−0.0037 (12)	0.0105 (12)	−0.0029 (12)
C14	0.0250 (14)	0.0225 (13)	0.0256 (14)	−0.0008 (11)	0.0116 (12)	−0.0019 (11)
C15	0.0245 (14)	0.0261 (14)	0.0278 (15)	0.0006 (11)	0.0094 (12)	0.0039 (11)
C16	0.0199 (13)	0.0287 (14)	0.0302 (15)	−0.0011 (11)	0.0092 (11)	0.0001 (12)
C17	0.0297 (15)	0.0207 (13)	0.0269 (14)	−0.0039 (11)	0.0131 (12)	−0.0039 (11)
C18	0.0307 (15)	0.0268 (14)	0.0245 (14)	0.0027 (12)	0.0074 (12)	0.0027 (11)
C19	0.0217 (14)	0.0264 (14)	0.0271 (14)	0.0003 (11)	0.0051 (12)	−0.0018 (11)
C20	0.0378 (18)	0.0431 (19)	0.0376 (18)	−0.0157 (15)	0.0124 (15)	0.0034 (15)

Geometric parameters (Å, º) top

S1—O1	1.429 (2)	C8—C10	1.380 (4)
S1—O2	1.439 (2)	C9—H9A	0.9800
S1—N1	1.650 (3)	C9—H9B	0.9800
S1—C5	1.760 (3)	C9—H9C	0.9800
O3—C13	1.212 (3)	C10—C11	1.489 (4)
O4—C17	1.365 (3)	C11—H11A	0.9800
O4—C20	1.435 (4)	C11—H11B	0.9800
N1—C8	1.428 (3)	C11—H11C	0.9800
N1—C9	1.482 (4)	C12—C13	1.521 (4)
N2—C7	1.340 (3)	C12—H12A	0.9900
N2—N3	1.361 (3)	C12—H12B	0.9900
N3—C10	1.360 (3)	C13—C14	1.489 (4)
N3—C12	1.451 (3)	C14—C15	1.397 (4)
C1—C2	1.386 (4)	C14—C19	1.399 (4)
C1—C6	1.394 (4)	C15—C16	1.387 (4)
C1—H1	0.9500	C15—H15	0.9500
C2—C3	1.385 (4)	C16—C17	1.388 (4)
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.386 (4)	C17—C18	1.397 (4)
C3—H3	0.9500	C18—C19	1.378 (4)
C4—C5	1.391 (4)	C18—H18	0.9500
C4—H4	0.9500	C19—H19	0.9500
C5—C6	1.400 (4)	C20—H20A	0.9800
C6—C7	1.457 (4)	C20—H20B	0.9800
C7—C8	1.407 (4)	C20—H20C	0.9800

O1—S1—O2	118.68 (14)	H9B—C9—H9C	109.5
O1—S1—N1	108.34 (13)	N3—C10—C8	104.5 (2)
O2—S1—N1	106.97 (13)	N3—C10—C11	124.4 (3)
O1—S1—C5	109.83 (13)	C8—C10—C11	131.1 (3)
O2—S1—C5	106.49 (13)	C10—C11—H11A	109.5
N1—S1—C5	105.80 (13)	C10—C11—H11B	109.5
C17—O4—C20	117.5 (2)	H11A—C11—H11B	109.5
C8—N1—C9	118.4 (2)	C10—C11—H11C	109.5
C8—N1—S1	111.63 (18)	H11A—C11—H11C	109.5
C9—N1—S1	118.2 (2)	H11B—C11—H11C	109.5
C7—N2—N3	103.7 (2)	N3—C12—C13	112.6 (2)
C10—N3—N2	114.1 (2)	N3—C12—H12A	109.1
C10—N3—C12	127.2 (2)	C13—C12—H12A	109.1
N2—N3—C12	118.7 (2)	N3—C12—H12B	109.1
C2—C1—C6	120.0 (3)	C13—C12—H12B	109.1
C2—C1—H1	120.0	H12A—C12—H12B	107.8
C6—C1—H1	120.0	O3—C13—C14	122.0 (3)
C3—C2—C1	121.1 (3)	O3—C13—C12	120.5 (3)
C3—C2—H2	119.5	C14—C13—C12	117.5 (2)
C1—C2—H2	119.5	C15—C14—C19	118.6 (2)
C2—C3—C4	120.1 (3)	C15—C14—C13	122.6 (2)
C2—C3—H3	120.0	C19—C14—C13	118.8 (2)
C4—C3—H3	120.0	C16—C15—C14	121.0 (3)
C3—C4—C5	118.7 (3)	C16—C15—H15	119.5
C3—C4—H4	120.7	C14—C15—H15	119.5
C5—C4—H4	120.7	C15—C16—C17	119.5 (3)
C4—C5—C6	122.0 (3)	C15—C16—H16	120.2
C4—C5—S1	118.8 (2)	C17—C16—H16	120.2
C6—C5—S1	118.9 (2)	O4—C17—C16	124.6 (3)
C1—C6—C5	118.1 (2)	O4—C17—C18	115.2 (2)
C1—C6—C7	124.0 (2)	C16—C17—C18	120.2 (3)
C5—C6—C7	117.8 (2)	C19—C18—C17	119.9 (3)
N2—C7—C8	111.0 (2)	C19—C18—H18	120.1
N2—C7—C6	125.0 (2)	C17—C18—H18	120.1
C8—C7—C6	123.9 (2)	C18—C19—C14	120.8 (3)
C10—C8—C7	106.6 (2)	C18—C19—H19	119.6
C10—C8—N1	128.6 (2)	C14—C19—H19	119.6
C7—C8—N1	124.8 (2)	O4—C20—H20A	109.5
N1—C9—H9A	109.5	O4—C20—H20B	109.5
N1—C9—H9B	109.5	H20A—C20—H20B	109.5
H9A—C9—H9B	109.5	O4—C20—H20C	109.5
N1—C9—H9C	109.5	H20A—C20—H20C	109.5
H9A—C9—H9C	109.5	H20B—C20—H20C	109.5

O1—S1—N1—C8	−162.2 (2)	C6—C7—C8—N1	2.2 (4)
O2—S1—N1—C8	68.8 (2)	C9—N1—C8—C10	69.1 (4)
C5—S1—N1—C8	−44.4 (2)	S1—N1—C8—C10	−148.3 (3)
O1—S1—N1—C9	−19.6 (3)	C9—N1—C8—C7	−112.1 (3)
O2—S1—N1—C9	−148.6 (2)	S1—N1—C8—C7	30.4 (4)
C5—S1—N1—C9	98.2 (2)	N2—N3—C10—C8	−0.1 (3)
C7—N2—N3—C10	0.6 (3)	C12—N3—C10—C8	−179.5 (3)
C7—N2—N3—C12	180.0 (2)	N2—N3—C10—C11	−178.1 (3)
C6—C1—C2—C3	2.2 (5)	C12—N3—C10—C11	2.5 (5)
C1—C2—C3—C4	−0.7 (5)	C7—C8—C10—N3	−0.4 (3)
C2—C3—C4—C5	−1.3 (4)	N1—C8—C10—N3	178.5 (3)
C3—C4—C5—C6	1.7 (4)	C7—C8—C10—C11	177.4 (3)
C3—C4—C5—S1	−171.8 (2)	N1—C8—C10—C11	−3.7 (5)
O1—S1—C5—C4	−33.1 (3)	C10—N3—C12—C13	−92.9 (3)
O2—S1—C5—C4	96.6 (2)	N2—N3—C12—C13	87.7 (3)
N1—S1—C5—C4	−149.8 (2)	N3—C12—C13—O3	0.4 (4)
O1—S1—C5—C6	153.1 (2)	N3—C12—C13—C14	−179.0 (2)
O2—S1—C5—C6	−77.2 (2)	O3—C13—C14—C15	172.2 (3)
N1—S1—C5—C6	36.4 (3)	C12—C13—C14—C15	−8.5 (4)
C2—C1—C6—C5	−1.8 (4)	O3—C13—C14—C19	−9.7 (4)
C2—C1—C6—C7	−179.8 (3)	C12—C13—C14—C19	169.6 (3)
C4—C5—C6—C1	−0.2 (4)	C19—C14—C15—C16	1.3 (4)
S1—C5—C6—C1	173.3 (2)	C13—C14—C15—C16	179.4 (3)
C4—C5—C6—C7	178.0 (3)	C14—C15—C16—C17	−0.9 (4)
S1—C5—C6—C7	−8.5 (3)	C20—O4—C17—C16	−1.8 (4)
N3—N2—C7—C8	−0.8 (3)	C20—O4—C17—C18	177.9 (3)
N3—N2—C7—C6	178.8 (2)	C15—C16—C17—O4	179.5 (3)
C1—C6—C7—N2	−15.4 (4)	C15—C16—C17—C18	−0.1 (4)
C5—C6—C7—N2	166.6 (3)	O4—C17—C18—C19	−179.0 (2)
C1—C6—C7—C8	164.2 (3)	C16—C17—C18—C19	0.7 (4)
C5—C6—C7—C8	−13.9 (4)	C17—C18—C19—C14	−0.2 (4)
N2—C7—C8—C10	0.8 (3)	C15—C14—C19—C18	−0.7 (4)
C6—C7—C8—C10	−178.8 (3)	C13—C14—C19—C18	−179.0 (3)
N2—C7—C8—N1	−178.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1ⁱ	0.95	2.34	3.216 (3)	154
C4—H4···O4ⁱⁱ	0.95	2.53	3.435 (4)	159
C9—H9A···O3ⁱⁱⁱ	0.98	2.54	3.335 (4)	138
C11—H11C···O2^iv	0.98	2.56	3.498 (4)	161
C12—H12B···O2^iv	0.99	2.33	3.309 (4)	170

Symmetry codes: (i) x, y−1, z; (ii) x+1/2, −y+1/2, z−1/2; (iii) −x+3/2, y+1/2, −z+1/2; (iv) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉N₃O₄S
M_r	397.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	13.862 (5), 8.079 (2), 17.748 (7)
β (°)	108.372 (18)
V (Å³)	1886.3 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.14 × 0.09 × 0.07

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.972, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	7270, 4221, 3206
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.132, 1.15
No. of reflections	4221
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.34

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···O1ⁱ	0.95	2.34	3.216 (3)	153.8
C4—H4···O4ⁱⁱ	0.95	2.53	3.435 (4)	158.9
C9—H9A···O3ⁱⁱⁱ	0.98	2.54	3.335 (4)	137.7
C11—H11C···O2^iv	0.98	2.56	3.498 (4)	161.4
C12—H12B···O2^iv	0.99	2.33	3.309 (4)	170.4

Symmetry codes: (i) x, y−1, z; (ii) x+1/2, −y+1/2, z−1/2; (iii) −x+3/2, y+1/2, −z+1/2; (iv) −x+1, −y+1, −z.

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. Lett. 16, 649–653. Web of Science CrossRef PubMed CAS Google Scholar
Farag, A. M., Mayhoub, A. S., Barakatb, S. E. & Bayomi, A. H. (2008). Bioorg. Med. Chem. 16, 881–889. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hooft, R. (1998). COLLECT. Nonius B V, 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
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Volume 68| Part 2| February 2012| Pages o458-o459

doi:10.1107/S1600536812001286

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

2-(3,4-Di­methyl-5,5-dioxo-2H,4H-pyrazolo­[4,3-c][1,2]benzo­thia­zin-2-yl)-1-(4-meth­­oxy­phen­yl)ethanone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-(3,4-Dimethyl-5,5-dioxo-2H,4H-pyrazolo[4,3-c][1,2]benzothiazin-2-yl)-1-(4-methoxyphenyl)ethanone