2-(3,4-Dimethyl-5,5-dioxo-2H,4H-pyrazolo-[4,3-c][1,2]benzothia-zin-2-yl)-1-(4-meth-oxy-phen-yl)ethanone.

In the title mol-ecule, C(20)H(19)N(3)O(4)S, the heterocyclic thia-zine 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, mol-ecules 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 = 397.44

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.132

S = 1.15

4221 reflections

256 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.34 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/S1600536812001286/lx2223sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812001286/lx2223Isup3.cml

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

C20H19N3O4S	F(000) = 832
Mr = 397.44	Dx = 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

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

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(Fo2) + (0.0125P)2 + 3.1849P] where P = (Fo2 + 2Fc2)/3
4221 reflections	(Δ/σ)max < 0.001
256 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.34 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	0.74841 (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*

	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)

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)

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···O2iv	0.98	2.56	3.498 (4)	161.
C12—H12B···O2iv	0.99	2.33	3.309 (4)	170.

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⋯O2iv	0.98	2.56	3.498 (4)	161
C12—H12B⋯O2iv	0.99	2.33	3.309 (4)	170

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