[2-(2,5-Dichloro­benz­yl)-4-hy­droxy-1,1-dioxo-2H-1,2-benzothia­zin-3-yl](phen­yl)methanone

Sattar, N.; Siddiqui, H.L.; Ahmad, M.; Akram, M.; Parvez, M.

doi:10.1107/S160053681201481X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1359

doi:10.1107/S160053681201481X

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[2-(2,5-Dichlorobenzyl)-4-hydroxy-1,1-dioxo-2H-1,2-benzothiazin-3-yl](phenyl)methanone

Nazia Sattar,^a Hamid Latif Siddiqui,^a ^* Matloob Ahmad,^b Muhammad Akram ^c and Masood Parvez ^d

^aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, ^bChemistry Department, Govt. College University, Faisalabad, Pakistan, ^cDepartment of Chemistry, Universiti Teknologi Malaysia, 81310 UTM Skudai, Johor, Darul Ta'zim, Malaysia, and ^dDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: drhamidlatif@hotmail.com

(Received 9 March 2012; accepted 4 April 2012; online 13 April 2012)

In the title molecule, C₂₂H₁₅Cl₂NO₄S, the heterocyclic thiazine ring adopts a half-chair conformation, with the S and N atoms displaced by 0.343 (5) and 0.402 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The molecular structure is consolidated by an intramolecular O—H⋯O hydrogen bond, which generates an S(?) ring. In the crystal, the molecules are linked by C—H⋯O interactions into [010] chains.

Related literature

For background information on the activity of anti-inflammatory and analgesic oxicams, see: Lombardino et al. (1971 ); Soler (1985 ); Carty et al. (1993 ); Turck et al. (1995 ); Blackham & Owen (1975 ). For the biological activity of benzothiazine derivatives, see: Zia-ur-Rehman et al. (2005 ); Ahmad et al. (2010 ). For the syntheses and crystal stuctures of related benzothiazine derivatives, see: Ahmad et al. (2011 ); Aslam et al. (2012 ).

Experimental

Crystal data

C₂₂H₁₅Cl₂NO₄S
M_r = 460.32
Monoclinic, P 2₁ /c
a = 12.8172 (5) Å
b = 9.9215 (4) Å
c = 16.7155 (5) Å
β = 110.511 (2)°
V = 1990.89 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 173 K
0.20 × 0.18 × 0.16 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.913, T_max = 0.930
16108 measured reflections
4592 independent reflections
3598 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.118
S = 1.11
4592 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.33 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
C3—H3⋯O4ⁱ	0.95	2.60	3.310 (4)	132
O3—H3O⋯O4	0.84	1.80	2.539 (3)	146
Symmetry code: (i) x, 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 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681201481X/rk2344sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201481X/rk2344Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201481X/rk2344Isup3.cml

checkCIF report

Comment top

Oxicam is the most recent class of non-steroidal anti-inflammatory drugs (NSAIDs) and includes molecules that are derived from 1,2-benzothiazine-1,1-dioxide nuclei which are found to be potent anti-inflammatory and analgesic agents, e.g., piroxicam (Lombardino et al., 1971), droxicam (Soler, 1985), ampiroxicam (Carty et al., 1993), meloxicam (Turck et al., 1995) and sudoxicam (Blackham & Owen, 1975), etc. Besides oxicam, a large number of benzothiazine derivatives are found to possess anti-microbial (Zia-ur-Rehman et al., 2005) and anti-oxidant activities (Ahmad et al., 2010). As part of our ongoing research we are interested in the synthesis and characterization of novel benzothiazine derivatives (Aslam et al., 2012; Ahmad et al., 2011). In this paper we report the synthesis, molecular and crystal structure of the title compound.

The bond distances and angles in the title compound (Fig. 1) agree well with the corresponding bond distances and angles reported for structures of closely related compounds (Ahmad et al., 2011; Aslam et al., 2012). The heterocyclic thiazine ring adopts a half chair conformation with atoms N1 and S1 displaced by 0.402 (5)Å and 0.343 (5)Å, respectively, on the opposite sides from the mean plane formed by the remaining ring atoms. The dihedral angle between the mean planes of benzene rings C1-C6 and C17-C22 is 31.17 (7)° while the mean planes of the benzene rings C1-C6 and C10-C15 are oriented at 35.09 (9)° with respect to each other. The molecular structure of the title compound is stabilized by intramolecular interactions O3–H3O···O4, C11–H11···N1 and C16–H16A···O2, etc, while the crystal packing is consolidated by C3–H3···O4ⁱ intermolecular nonclassical hydrogen bonds resulting in chains of molecules lying along the b-axis (Fig. 2 and Table 1). Symmetry code: (i) x, y+1, z.

Related literature top

For background information on the activity of anti-inflammatory and analgesic oxicams, see: Lombardino et al. (1971); Soler (1985); Carty et al. (1993); Turck et al. (1995); Blackham & Owen (1975). For the biological activity of benzothiazine derivatives, see: Zia-ur-Rehman et al. (2005); Ahmad et al. (2010). For the syntheses and crystal stuctures of novel benzothiazine derivatives, see: Ahmad et al. (2011); Aslam et al. (2012).

Experimental top

A mixture of 3-benzoyl-4-hydroxy-2H-1,2-benzothiazine 1,1-dioxide (1.0 g, 3.32 mmol), aqueous sodium hydroxide (0.26 g, 6.6 mmol) and 2-(bromomethyl)-1,4-dichlorobenzene (0.80 g, 3.32 mmol) in acetone (10 ml) was subjected to ultrasonic irradiation for 20 minutes at 318 K. The reaction mixture was then acidified to pH = 3 by using dilute hydrochloric acid. The precipitates were filtered, washed with excess of distilled water and dried at room temperature to get chrome yellow powder of the title compound (1.38 g, 90.3%). The crystals suitable for X-ray crystallographic analysis were grown from methanol by slow evaporation at room temperature.

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 (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 25% probability level. The H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A part of the unit cell showing intermolecular and intramolecular hydrogen bonds (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity.

[2-(2,5-Dichlorobenzyl)-4-hydroxy-1,1-dioxo-2H-1,2-benzothiazin- 3-yl](phenyl)methanone top

Crystal data top

C₂₂H₁₅Cl₂NO₄S	F(000) = 944
M_r = 460.32	D_x = 1.536 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8696 reflections
a = 12.8172 (5) Å	θ = 1.0–27.5°
b = 9.9215 (4) Å	µ = 0.46 mm⁻¹
c = 16.7155 (5) Å	T = 173 K
β = 110.511 (2)°	Prism, yellow
V = 1990.89 (13) Å³	0.20 × 0.18 × 0.16 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	4592 independent reflections
Radiation source: fine-focus sealed tube	3598 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
ω and ϕ scans	θ_max = 27.6°, θ_min = 2.7°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −16→16
T_min = 0.913, T_max = 0.930	k = −12→12
16108 measured reflections	l = −21→20

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0232P)² + 2.3517P] where P = (F_o² + 2F_c²)/3
4592 reflections	(Δ/σ)_max = 0.001
272 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₂₂H₁₅Cl₂NO₄S	V = 1990.89 (13) Å³
M_r = 460.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.8172 (5) Å	µ = 0.46 mm⁻¹
b = 9.9215 (4) Å	T = 173 K
c = 16.7155 (5) Å	0.20 × 0.18 × 0.16 mm
β = 110.511 (2)°

Data collection top

Nonius KappaCCD diffractometer	4592 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	3598 reflections with I > 2σ(I)
T_min = 0.913, T_max = 0.930	R_int = 0.055
16108 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.11	Δρ_max = 0.33 e Å⁻³
4592 reflections	Δρ_min = −0.44 e Å⁻³
272 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.52481 (7)	−0.04749 (10)	0.39033 (6)	0.0658 (3)
Cl2	0.50174 (9)	0.57915 (12)	0.37257 (7)	0.0804 (3)
S1	0.87675 (5)	0.25684 (7)	0.53887 (4)	0.03478 (16)
O1	0.98780 (15)	0.2067 (2)	0.56375 (12)	0.0457 (5)
O2	0.84712 (17)	0.3467 (2)	0.59407 (11)	0.0465 (5)
O3	0.79566 (17)	0.0186 (2)	0.31269 (11)	0.0418 (5)
H3O	0.7866	−0.0624	0.3235	0.050*
O4	0.77251 (15)	−0.18006 (19)	0.40080 (11)	0.0408 (5)
N1	0.79342 (17)	0.1262 (2)	0.52149 (12)	0.0331 (5)
C1	0.8421 (2)	0.3280 (3)	0.43643 (16)	0.0339 (6)
C2	0.8521 (2)	0.4653 (3)	0.42629 (18)	0.0406 (6)
H2	0.8739	0.5236	0.4744	0.049*
C3	0.8297 (2)	0.5165 (3)	0.34482 (19)	0.0465 (7)
H3	0.8365	0.6104	0.3369	0.056*
C4	0.7977 (3)	0.4316 (3)	0.27565 (18)	0.0483 (7)
H4	0.7830	0.4676	0.2201	0.058*
C5	0.7866 (2)	0.2949 (3)	0.28534 (17)	0.0421 (7)
H5	0.7638	0.2378	0.2366	0.050*
C6	0.8089 (2)	0.2404 (3)	0.36662 (15)	0.0318 (5)
C7	0.7989 (2)	0.0952 (3)	0.37903 (15)	0.0326 (6)
C8	0.7978 (2)	0.0396 (3)	0.45361 (14)	0.0307 (5)
C9	0.7971 (2)	−0.1051 (3)	0.46462 (16)	0.0334 (6)
C10	0.8276 (2)	−0.1656 (3)	0.55114 (16)	0.0357 (6)
C11	0.9160 (2)	−0.1140 (3)	0.61913 (17)	0.0403 (6)
H11	0.9531	−0.0345	0.6119	0.048*
C12	0.9498 (2)	−0.1792 (3)	0.69745 (18)	0.0463 (7)
H12	1.0107	−0.1448	0.7438	0.056*
C13	0.8954 (3)	−0.2934 (3)	0.70810 (19)	0.0498 (8)
H13	0.9190	−0.3376	0.7619	0.060*
C14	0.8066 (3)	−0.3445 (3)	0.6410 (2)	0.0505 (8)
H14	0.7685	−0.4226	0.6491	0.061*
C15	0.7735 (3)	−0.2815 (3)	0.56220 (19)	0.0448 (7)
H15	0.7137	−0.3175	0.5157	0.054*
C16	0.6823 (2)	0.1408 (3)	0.53043 (16)	0.0376 (6)
H16A	0.6906	0.1968	0.5813	0.045*
H16B	0.6560	0.0507	0.5403	0.045*
C17	0.5954 (2)	0.2036 (3)	0.45391 (16)	0.0396 (6)
C18	0.5232 (2)	0.1274 (4)	0.38632 (19)	0.0502 (8)
C19	0.4486 (3)	0.1900 (5)	0.3150 (2)	0.0661 (11)
H19	0.4009	0.1372	0.2695	0.079*
C20	0.4435 (3)	0.3273 (5)	0.3101 (2)	0.0685 (11)
H20	0.3933	0.3699	0.2606	0.082*
C21	0.5114 (3)	0.4044 (4)	0.37701 (19)	0.0564 (9)
C22	0.5870 (2)	0.3432 (3)	0.44836 (17)	0.0437 (7)
H22	0.6336	0.3972	0.4938	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0454 (4)	0.0807 (7)	0.0762 (6)	−0.0194 (4)	0.0274 (4)	−0.0311 (5)
Cl2	0.0780 (7)	0.0882 (8)	0.0780 (6)	0.0331 (6)	0.0310 (5)	0.0324 (6)
S1	0.0355 (3)	0.0382 (4)	0.0259 (3)	−0.0025 (3)	0.0048 (2)	−0.0050 (3)
O1	0.0316 (10)	0.0547 (13)	0.0402 (10)	−0.0033 (9)	−0.0006 (8)	−0.0019 (9)
O2	0.0582 (13)	0.0452 (12)	0.0332 (10)	−0.0025 (10)	0.0124 (9)	−0.0114 (9)
O3	0.0569 (12)	0.0388 (11)	0.0303 (9)	−0.0066 (10)	0.0160 (9)	−0.0086 (8)
O4	0.0440 (11)	0.0395 (11)	0.0358 (10)	−0.0041 (9)	0.0102 (8)	−0.0087 (8)
N1	0.0342 (11)	0.0379 (12)	0.0265 (10)	−0.0022 (10)	0.0100 (9)	−0.0041 (9)
C1	0.0311 (13)	0.0375 (15)	0.0310 (13)	−0.0010 (11)	0.0082 (10)	−0.0024 (11)
C2	0.0414 (15)	0.0378 (15)	0.0399 (15)	−0.0015 (12)	0.0108 (12)	−0.0062 (12)
C3	0.0529 (18)	0.0349 (16)	0.0515 (17)	0.0000 (13)	0.0178 (14)	0.0047 (13)
C4	0.0578 (19)	0.0464 (18)	0.0389 (15)	−0.0002 (15)	0.0146 (14)	0.0081 (13)
C5	0.0469 (16)	0.0474 (17)	0.0304 (13)	−0.0005 (13)	0.0117 (12)	−0.0024 (12)
C6	0.0305 (12)	0.0366 (14)	0.0276 (11)	−0.0021 (11)	0.0092 (10)	−0.0020 (11)
C7	0.0281 (12)	0.0398 (15)	0.0290 (12)	−0.0016 (11)	0.0088 (10)	−0.0074 (11)
C8	0.0276 (12)	0.0380 (14)	0.0246 (11)	−0.0008 (11)	0.0066 (9)	−0.0035 (10)
C9	0.0274 (12)	0.0388 (15)	0.0337 (13)	−0.0021 (11)	0.0103 (10)	−0.0028 (11)
C10	0.0379 (14)	0.0354 (14)	0.0349 (13)	0.0042 (12)	0.0140 (11)	0.0028 (11)
C11	0.0391 (15)	0.0417 (16)	0.0387 (14)	0.0041 (12)	0.0119 (12)	0.0034 (12)
C12	0.0454 (16)	0.0536 (19)	0.0365 (15)	0.0096 (14)	0.0102 (13)	0.0026 (13)
C13	0.062 (2)	0.0496 (19)	0.0413 (16)	0.0147 (16)	0.0226 (15)	0.0116 (14)
C14	0.067 (2)	0.0375 (17)	0.0579 (19)	0.0017 (15)	0.0351 (17)	0.0071 (14)
C15	0.0504 (17)	0.0423 (17)	0.0449 (16)	−0.0002 (13)	0.0206 (14)	−0.0016 (13)
C16	0.0365 (14)	0.0490 (17)	0.0306 (13)	−0.0006 (12)	0.0156 (11)	−0.0037 (12)
C17	0.0292 (13)	0.0628 (19)	0.0296 (13)	0.0001 (13)	0.0138 (11)	−0.0029 (12)
C18	0.0313 (14)	0.079 (2)	0.0444 (16)	−0.0037 (15)	0.0190 (13)	−0.0138 (16)
C19	0.0351 (17)	0.119 (4)	0.0399 (18)	−0.002 (2)	0.0073 (14)	−0.013 (2)
C20	0.0389 (18)	0.124 (4)	0.0366 (17)	0.018 (2)	0.0057 (14)	0.015 (2)
C21	0.0395 (16)	0.088 (3)	0.0434 (17)	0.0170 (17)	0.0171 (14)	0.0127 (17)
C22	0.0343 (14)	0.065 (2)	0.0340 (14)	0.0068 (14)	0.0142 (12)	0.0029 (13)

Geometric parameters (Å, º) top

Cl1—C18	1.736 (4)	C9—C10	1.486 (3)
Cl2—C21	1.738 (4)	C10—C15	1.389 (4)
S1—O1	1.425 (2)	C10—C11	1.391 (4)
S1—O2	1.4268 (19)	C11—C12	1.386 (4)
S1—N1	1.640 (2)	C11—H11	0.9500
S1—C1	1.759 (3)	C12—C13	1.375 (4)
O3—C7	1.333 (3)	C12—H12	0.9500
O3—H3O	0.8400	C13—C14	1.384 (4)
O4—C9	1.247 (3)	C13—H13	0.9500
N1—C8	1.440 (3)	C14—C15	1.384 (4)
N1—C16	1.491 (3)	C14—H14	0.9500
C1—C2	1.384 (4)	C15—H15	0.9500
C1—C6	1.397 (3)	C16—C17	1.506 (4)
C2—C3	1.386 (4)	C16—H16A	0.9900
C2—H2	0.9500	C16—H16B	0.9900
C3—C4	1.372 (4)	C17—C22	1.389 (4)
C3—H3	0.9500	C17—C18	1.404 (4)
C4—C5	1.379 (4)	C18—C19	1.387 (5)
C4—H4	0.9500	C19—C20	1.365 (6)
C5—C6	1.396 (4)	C19—H19	0.9500
C5—H5	0.9500	C20—C21	1.383 (5)
C6—C7	1.467 (4)	C20—H20	0.9500
C7—C8	1.368 (3)	C21—C22	1.386 (4)
C8—C9	1.448 (4)	C22—H22	0.9500

O1—S1—O2	119.62 (12)	C12—C11—C10	119.7 (3)
O1—S1—N1	107.33 (12)	C12—C11—H11	120.1
O2—S1—N1	107.70 (12)	C10—C11—H11	120.1
O1—S1—C1	108.03 (12)	C13—C12—C11	120.1 (3)
O2—S1—C1	110.19 (12)	C13—C12—H12	119.9
N1—S1—C1	102.62 (11)	C11—C12—H12	119.9
C7—O3—H3O	109.5	C12—C13—C14	120.5 (3)
C8—N1—C16	116.06 (19)	C12—C13—H13	119.7
C8—N1—S1	114.13 (16)	C14—C13—H13	119.7
C16—N1—S1	119.42 (18)	C13—C14—C15	119.8 (3)
C2—C1—C6	121.6 (2)	C13—C14—H14	120.1
C2—C1—S1	120.8 (2)	C15—C14—H14	120.1
C6—C1—S1	117.5 (2)	C14—C15—C10	120.0 (3)
C1—C2—C3	119.0 (3)	C14—C15—H15	120.0
C1—C2—H2	120.5	C10—C15—H15	120.0
C3—C2—H2	120.5	N1—C16—C17	113.8 (2)
C4—C3—C2	120.1 (3)	N1—C16—H16A	108.8
C4—C3—H3	120.0	C17—C16—H16A	108.8
C2—C3—H3	120.0	N1—C16—H16B	108.8
C3—C4—C5	121.2 (3)	C17—C16—H16B	108.8
C3—C4—H4	119.4	H16A—C16—H16B	107.7
C5—C4—H4	119.4	C22—C17—C18	118.0 (3)
C4—C5—C6	120.1 (3)	C22—C17—C16	119.1 (3)
C4—C5—H5	120.0	C18—C17—C16	122.9 (3)
C6—C5—H5	120.0	C19—C18—C17	120.7 (3)
C5—C6—C1	118.1 (2)	C19—C18—Cl1	118.4 (3)
C5—C6—C7	121.3 (2)	C17—C18—Cl1	120.8 (3)
C1—C6—C7	120.6 (2)	C20—C19—C18	120.3 (3)
O3—C7—C8	121.4 (2)	C20—C19—H19	119.9
O3—C7—C6	114.9 (2)	C18—C19—H19	119.9
C8—C7—C6	123.7 (2)	C19—C20—C21	119.9 (3)
C7—C8—N1	119.5 (2)	C19—C20—H20	120.0
C7—C8—C9	121.2 (2)	C21—C20—H20	120.0
N1—C8—C9	119.2 (2)	C20—C21—C22	120.4 (4)
O4—C9—C8	119.6 (2)	C20—C21—Cl2	120.1 (3)
O4—C9—C10	119.6 (2)	C22—C21—Cl2	119.4 (3)
C8—C9—C10	120.8 (2)	C21—C22—C17	120.5 (3)
C15—C10—C11	119.9 (3)	C21—C22—H22	119.7
C15—C10—C9	119.4 (2)	C17—C22—H22	119.7
C11—C10—C9	120.5 (2)

O1—S1—N1—C8	−61.89 (19)	S1—N1—C8—C9	138.3 (2)
O2—S1—N1—C8	168.09 (17)	C7—C8—C9—O4	−16.1 (4)
C1—S1—N1—C8	51.8 (2)	N1—C8—C9—O4	161.9 (2)
O1—S1—N1—C16	154.46 (18)	C7—C8—C9—C10	162.6 (2)
O2—S1—N1—C16	24.5 (2)	N1—C8—C9—C10	−19.5 (3)
C1—S1—N1—C16	−91.83 (19)	O4—C9—C10—C15	−36.4 (4)
O1—S1—C1—C2	−96.7 (2)	C8—C9—C10—C15	144.9 (3)
O2—S1—C1—C2	35.6 (3)	O4—C9—C10—C11	138.0 (3)
N1—S1—C1—C2	150.1 (2)	C8—C9—C10—C11	−40.7 (4)
O1—S1—C1—C6	80.8 (2)	C15—C10—C11—C12	0.3 (4)
O2—S1—C1—C6	−146.9 (2)	C9—C10—C11—C12	−174.1 (3)
N1—S1—C1—C6	−32.4 (2)	C10—C11—C12—C13	−0.7 (4)
C6—C1—C2—C3	−0.8 (4)	C11—C12—C13—C14	0.0 (4)
S1—C1—C2—C3	176.6 (2)	C12—C13—C14—C15	1.1 (5)
C1—C2—C3—C4	0.3 (4)	C13—C14—C15—C10	−1.5 (4)
C2—C3—C4—C5	0.3 (5)	C11—C10—C15—C14	0.8 (4)
C3—C4—C5—C6	−0.5 (5)	C9—C10—C15—C14	175.3 (3)
C4—C5—C6—C1	0.0 (4)	C8—N1—C16—C17	−62.6 (3)
C4—C5—C6—C7	−179.3 (3)	S1—N1—C16—C17	80.4 (3)
C2—C1—C6—C5	0.7 (4)	N1—C16—C17—C22	−86.3 (3)
S1—C1—C6—C5	−176.8 (2)	N1—C16—C17—C18	92.3 (3)
C2—C1—C6—C7	−180.0 (2)	C22—C17—C18—C19	2.1 (4)
S1—C1—C6—C7	2.5 (3)	C16—C17—C18—C19	−176.5 (3)
C5—C6—C7—O3	16.2 (4)	C22—C17—C18—Cl1	−177.5 (2)
C1—C6—C7—O3	−163.1 (2)	C16—C17—C18—Cl1	3.9 (4)
C5—C6—C7—C8	−166.5 (2)	C17—C18—C19—C20	−0.7 (5)
C1—C6—C7—C8	14.2 (4)	Cl1—C18—C19—C20	178.9 (3)
O3—C7—C8—N1	−175.6 (2)	C18—C19—C20—C21	−1.2 (5)
C6—C7—C8—N1	7.3 (4)	C19—C20—C21—C22	1.8 (5)
O3—C7—C8—C9	2.3 (4)	C19—C20—C21—Cl2	−177.8 (3)
C6—C7—C8—C9	−174.8 (2)	C20—C21—C22—C17	−0.4 (4)
C16—N1—C8—C7	101.2 (3)	Cl2—C21—C22—C17	179.2 (2)
S1—N1—C8—C7	−43.8 (3)	C18—C17—C22—C21	−1.5 (4)
C16—N1—C8—C9	−76.8 (3)	C16—C17—C22—C21	177.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4ⁱ	0.95	2.60	3.310 (4)	132
O3—H3O···O4	0.84	1.80	2.539 (3)	146
C11—H11···N1	0.95	2.62	3.003 (3)	105
C16—H16A···O2	0.99	2.45	2.862 (3)	105
C16—H16B···Cl1	0.99	2.67	3.120 (3)	108

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₅Cl₂NO₄S
M_r	460.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	12.8172 (5), 9.9215 (4), 16.7155 (5)
β (°)	110.511 (2)
V (Å³)	1990.89 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.913, 0.930
No. of measured, independent and observed [I > 2σ(I)] reflections	16108, 4592, 3598
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.118, 1.11
No. of reflections	4592
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.44

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4ⁱ	0.95	2.60	3.310 (4)	132.0
O3—H3O···O4	0.84	1.80	2.539 (3)	146.3
C11—H11···N1	0.95	2.62	3.003 (3)	104.7
C16—H16A···O2	0.99	2.45	2.862 (3)	104.7
C16—H16B···Cl1	0.99	2.67	3.120 (3)	108.2

Symmetry code: (i) x, 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

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Volume 68| Part 5| May 2012| Page o1359

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

[2-(2,5-Di­chloro­benz­yl)-4-hy­dr­oxy-1,1-dioxo-2H-1,2-benzo­thia­zin-3-yl](phen­yl)methanone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

[2-(2,5-Dichlorobenzyl)-4-hydroxy-1,1-dioxo-2H-1,2-benzothiazin-3-yl](phenyl)methanone