2-Benzoyl-2H-1,4-benzothia­zin-3(4H)-one

Shahwar, D.; Tahir, M.N.; Ahmad, N.; Raza, M.A.; Khan, M.A.

doi:10.1107/S1600536810029582

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2145

https://doi.org/10.1107/S1600536810029582

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2-Benzoyl-2H-1,4-benzothiazin-3(4H)-one

Durre Shahwar,^a M. Nawaz Tahir,^b ^* Naeem Ahmad,^a Muhammad Asam Raza ^a and Muhammad Akmal Khan ^a

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 20 July 2010; accepted 25 July 2010; online 31 July 2010)

In the title compound, C₁₅H₁₁NO₂S, the dihedral angle between the aromatic rings is 80.35 (7)°. The heterocyclic six-membered ring is not planar: the puckering parameters of this ring are Q = 0.5308 (15) Å, θ = 63.11 (18) and φ = 23.5 (2)°. The molecules are linked into inversion dimers with R₂²(8) ring motifs by pairs of N—H⋯O hydrogen bonds. The dimers are interlinked into polymeric sheets extending parallel to the bc plane by C—H⋯O hydrogen bonds, generating R₂¹(7) ring motifs. π–π interactions occur between the benzoyl phenyl rings with centroid–centroid separations of 3.9187 (15) Å.

Related literature

For puckering parameters, see: Cremer & Pople (1975 ). For the synthesis and antimicrobial activity of benzimidazole derivatives, see: Güven et al. (2007 ): Nofal et al. (2002 ). For related structures, see: Beryozkina et al. (2004 ): Kumaradhas & Nirmala (1997 ): Zhang et al. (2008 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₁NO₂S
M_r = 269.31
Monoclinic, P 2₁ /n
a = 9.1323 (3) Å
b = 15.2893 (4) Å
c = 10.5214 (4) Å
β = 114.669 (1)°
V = 1334.99 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.25 × 0.20 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.939, T_max = 0.950
10387 measured reflections
2399 independent reflections
2064 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.103
S = 1.04
2399 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	1.98	2.8383 (19)	179
C2—H2⋯O1ⁱⁱ	0.93	2.55	3.453 (2)	165
C8—H8⋯O1ⁱⁱ	0.98	2.36	3.170 (2)	140
Symmetry codes: (i) -x, -y, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810029582/si2280sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810029582/si2280Isup2.hkl

checkCIF report

Comment top

Benzothiazin molecules exhibit a broad spectrum of biological activity such as antifungal (Güven et al., 2007) and antibacterial (Nofal et al., 2002) properties. Our group is engaged in preparation and evaluation of biological activities of such type of compounds.

The crystal structures of (II) i.e., 2-(2-(4-bromophenyl)-2-oxoethyl)-4H-benzo-1,4-thiazin-3-one (Beryozkina et al., 2004), (III) 2-(4-chlorobenzoylmethyl)-2H-1,4-benzothiazin-3(4H)-one (Zhang et al., 2008) and (IV) (±)-2-(hydroxy(4-methoxyphenyl)methyl)-2H-1,4-benzothiazin- 3(4H)-one monohydrate (Kumaradhas & Nirmala et al., 1997) have been published which are related to title compound (I), (Fig. 1).

In (I), the benzene rings A (C1—C6) and B (C10—C15) are planar with r. m. s. deviations of 0.0045 and 0.0084 Å, respectively. The dihedral angle between A/B is 80.35 (7)°. The heterocyclic six membered ring C (C8/C9/N1/C10/C11/S1) fused with phenyl ring group B is not planar. The confirmation of this ring may be described by the puckering parameters (Cremer & Pople, 1975): Q = 0.5308 (15) Å, θ = 63.11 (18)°, φ = 23.5 (2)°. The molecules are stabilized in the form of dimers (Fig. 2) due to N—H···O type of H-bondings (Table 1) with R₂²(8) ring motifs (Bernstein et al., 1995). The dimers are interlinked in the form of polymeric sheets extending parallel to bc-plane due to C—H···O type of H-bondings (Table 1, Fig. 2) and complete R₂¹(7) ring motifs. There exist π–π interaction between the centroids of carbonyl containing phenyl rings at a separation of 3.9187 (15) Å [symmetry code: -x, 1 - y, 1 - z].

Related literature top

For puckering parameters, see: Cremer & Pople (1975). For the synthesis and antimicrobial activity of benzimidazole derivatives, see: Güven et al. (2007): Nofal et al. (2002). For related structures, see: Beryozkina et al. (2004): Kumaradhas & Nirmala (1997): Zhang et al. (2008). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

2-Aminothiophenol (0.01 M, 1.08 ml) and ethyl benzoyl acetate (0.01 M, 1.73) were added to 5 ml dimethylsulfoxide. Resulting mixture was refluxed for 1 h and left overnight at room temperature. The separated solid was filtered, washed with petroleum ether and recrystallized with methanol to affoard light yellow plates.

Structure description top

For puckering parameters, see: Cremer & Pople (1975). For the synthesis and antimicrobial activity of benzimidazole derivatives, see: Güven et al. (2007): Nofal et al. (2002). For related structures, see: Beryozkina et al. (2004): Kumaradhas & Nirmala (1997): Zhang et al. (2008). For graph-set notation, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form dimers which are interlinked in the form of polymeric sheets. The H-atoms not involved in H-bodings are omitted for clarity.

2-Benzoyl-2H-1,4-benzothiazin-3(4H)-one top

Crystal data top

C₁₅H₁₁NO₂S	F(000) = 560
M_r = 269.31	D_x = 1.340 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2064 reflections
a = 9.1323 (3) Å	θ = 3.4–25.3°
b = 15.2893 (4) Å	µ = 0.24 mm⁻¹
c = 10.5214 (4) Å	T = 296 K
β = 114.669 (1)°	Plate, light yellow
V = 1334.99 (8) Å³	0.25 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2399 independent reflections
Radiation source: fine-focus sealed tube	2064 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 8.10 pixels mm^-1	θ_max = 25.3°, θ_min = 3.4°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −18→18
T_min = 0.939, T_max = 0.950	l = −12→12
10387 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.046P)² + 0.5415P] where P = (F_o² + 2F_c²)/3
2399 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₅H₁₁NO₂S	V = 1334.99 (8) Å³
M_r = 269.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.1323 (3) Å	µ = 0.24 mm⁻¹
b = 15.2893 (4) Å	T = 296 K
c = 10.5214 (4) Å	0.25 × 0.20 × 0.10 mm
β = 114.669 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2399 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2064 reflections with I > 2σ(I)
T_min = 0.939, T_max = 0.950	R_int = 0.023
10387 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.04	Δρ_max = 0.29 e Å⁻³
2399 reflections	Δρ_min = −0.41 e Å⁻³
172 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	−0.02233 (6)	0.25059 (3)	0.25961 (5)	0.0528 (2)
O1	0.07429 (16)	0.26350 (9)	0.61431 (13)	0.0569 (4)
O2	−0.15131 (15)	0.08259 (8)	0.46234 (17)	0.0603 (5)
N1	0.08715 (16)	0.09439 (9)	0.45062 (15)	0.0419 (4)
C1	−0.1244 (2)	0.36835 (10)	0.49255 (17)	0.0399 (5)
C2	−0.2555 (2)	0.39269 (12)	0.3713 (2)	0.0508 (6)
C3	−0.3331 (3)	0.47100 (14)	0.3657 (3)	0.0720 (8)
C4	−0.2798 (3)	0.52592 (15)	0.4793 (3)	0.0827 (10)
C5	−0.1488 (3)	0.50307 (15)	0.5989 (3)	0.0795 (9)
C6	−0.0712 (3)	0.42488 (13)	0.6065 (2)	0.0584 (7)
C7	−0.04028 (19)	0.28361 (10)	0.50775 (16)	0.0372 (5)
C8	−0.09851 (19)	0.21947 (10)	0.38628 (16)	0.0365 (5)
C9	−0.05515 (19)	0.12647 (10)	0.43619 (18)	0.0401 (5)
C10	0.2099 (2)	0.13817 (11)	0.42926 (18)	0.0402 (5)
C11	0.1776 (2)	0.21359 (12)	0.34898 (19)	0.0470 (6)
C12	0.3019 (3)	0.25556 (14)	0.3316 (3)	0.0678 (9)
C13	0.4547 (3)	0.22130 (18)	0.3895 (3)	0.0782 (10)
C14	0.4862 (3)	0.14499 (16)	0.4662 (3)	0.0672 (8)
C15	0.3646 (2)	0.10353 (13)	0.4873 (2)	0.0505 (6)
H1	0.10555	0.04056	0.47600	0.0503*
H2	−0.29116	0.35614	0.29359	0.0609*
H3	−0.42186	0.48663	0.28466	0.0864*
H4	−0.33252	0.57860	0.47507	0.0992*
H5	−0.11211	0.54072	0.67529	0.0952*
H6	0.01709	0.40971	0.68826	0.0701*
H8	−0.21632	0.22331	0.34039	0.0439*
H12	0.28195	0.30724	0.28049	0.0813*
H13	0.53768	0.24977	0.37689	0.0939*
H14	0.58965	0.12159	0.50366	0.0807*
H15	0.38578	0.05252	0.54010	0.0606*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0689 (4)	0.0489 (3)	0.0425 (3)	0.0067 (2)	0.0251 (2)	0.0100 (2)
O1	0.0513 (8)	0.0588 (8)	0.0406 (7)	0.0149 (6)	−0.0005 (6)	−0.0002 (6)
O2	0.0459 (7)	0.0373 (7)	0.1062 (12)	0.0049 (6)	0.0402 (8)	0.0184 (7)
N1	0.0378 (7)	0.0277 (7)	0.0595 (9)	0.0014 (6)	0.0196 (7)	0.0057 (6)
C1	0.0436 (9)	0.0314 (8)	0.0425 (9)	−0.0020 (7)	0.0157 (7)	0.0031 (7)
C2	0.0540 (11)	0.0365 (9)	0.0502 (10)	0.0051 (8)	0.0103 (9)	0.0046 (8)
C3	0.0762 (15)	0.0488 (12)	0.0743 (14)	0.0220 (11)	0.0149 (12)	0.0147 (11)
C4	0.112 (2)	0.0438 (12)	0.0907 (18)	0.0277 (13)	0.0407 (16)	0.0041 (12)
C5	0.114 (2)	0.0478 (12)	0.0713 (15)	0.0101 (13)	0.0334 (14)	−0.0125 (11)
C6	0.0721 (13)	0.0466 (11)	0.0477 (10)	0.0033 (10)	0.0163 (10)	−0.0022 (8)
C7	0.0359 (9)	0.0358 (9)	0.0365 (8)	−0.0010 (7)	0.0119 (7)	0.0046 (7)
C8	0.0334 (8)	0.0314 (8)	0.0388 (8)	0.0014 (6)	0.0092 (7)	0.0035 (6)
C9	0.0354 (9)	0.0310 (8)	0.0513 (10)	−0.0004 (7)	0.0154 (7)	0.0032 (7)
C10	0.0412 (9)	0.0362 (9)	0.0468 (9)	−0.0054 (7)	0.0220 (7)	−0.0101 (7)
C11	0.0581 (11)	0.0420 (10)	0.0508 (10)	−0.0057 (8)	0.0326 (9)	−0.0062 (8)
C12	0.0860 (17)	0.0564 (13)	0.0891 (16)	−0.0114 (11)	0.0645 (14)	−0.0042 (11)
C13	0.0770 (16)	0.0757 (16)	0.113 (2)	−0.0253 (13)	0.0704 (16)	−0.0254 (15)
C14	0.0474 (11)	0.0784 (16)	0.0876 (16)	−0.0081 (10)	0.0398 (11)	−0.0316 (13)
C15	0.0437 (10)	0.0492 (10)	0.0607 (11)	0.0002 (8)	0.0239 (9)	−0.0144 (9)

Geometric parameters (Å, º) top

S1—C8	1.8057 (18)	C10—C15	1.389 (3)
S1—C11	1.762 (2)	C10—C11	1.386 (2)
O1—C7	1.211 (2)	C11—C12	1.381 (3)
O2—C9	1.224 (2)	C12—C13	1.372 (4)
N1—C9	1.337 (2)	C13—C14	1.379 (4)
N1—C10	1.402 (2)	C14—C15	1.375 (4)
N1—H1	0.8600	C2—H2	0.9300
C1—C6	1.391 (3)	C3—H3	0.9300
C1—C7	1.481 (2)	C4—H4	0.9300
C1—C2	1.387 (3)	C5—H5	0.9300
C2—C3	1.380 (3)	C6—H6	0.9300
C3—C4	1.373 (4)	C8—H8	0.9800
C4—C5	1.371 (4)	C12—H12	0.9300
C5—C6	1.375 (3)	C13—H13	0.9300
C7—C8	1.520 (2)	C14—H14	0.9300
C8—C9	1.510 (2)	C15—H15	0.9300

S1···O1	3.4635 (14)	C11···O1	3.386 (2)
S1···N1	3.0108 (15)	C14···S1ⁱⁱ	3.505 (3)
S1···C2	3.567 (2)	C15···S1ⁱⁱ	3.432 (2)
S1···C15ⁱ	3.432 (2)	C2···H8	2.6500
S1···O1ⁱ	3.3545 (16)	C2···H13^iv	2.9000
S1···C14ⁱ	3.505 (3)	C8···H2	2.6400
S1···H2	3.0800	C9···H1ⁱⁱⁱ	2.8200
O1···S1	3.4635 (14)	C9···H3^v	3.1000
O1···N1	3.136 (2)	H1···H15	2.3700
O1···C10	3.318 (2)	H1···O2ⁱⁱⁱ	1.9800
O1···C11	3.386 (2)	H1···C9ⁱⁱⁱ	2.8200
O1···S1ⁱⁱ	3.3545 (16)	H1···H1ⁱⁱⁱ	2.5100
O1···C8ⁱⁱ	3.170 (2)	H2···S1	3.0800
O2···N1ⁱⁱⁱ	2.8383 (19)	H2···C8	2.6400
O1···H6	2.4900	H2···H8	2.1300
O1···H8ⁱⁱ	2.3600	H2···O1ⁱ	2.5500
O1···H2ⁱⁱ	2.5500	H3···N1^vi	2.8300
O2···H14^iv	2.6500	H3···C9^vi	3.1000
O2···H1ⁱⁱⁱ	1.9800	H6···O1	2.4900
N1···S1	3.0108 (15)	H8···C2	2.6500
N1···O1	3.136 (2)	H8···H2	2.1300
N1···O2ⁱⁱⁱ	2.8383 (19)	H8···H13^iv	2.4700
N1···H3^v	2.8300	H8···O1ⁱ	2.3600
C2···S1	3.567 (2)	H13···C2^vii	2.9000
C7···C10	3.524 (3)	H13···H8^vii	2.4700
C8···O1ⁱ	3.170 (2)	H14···O2^vii	2.6500
C10···O1	3.318 (2)	H15···H1	2.3700
C10···C7	3.524 (3)

C8—S1—C11	98.87 (9)	S1—C11—C12	120.40 (16)
C9—N1—C10	127.66 (14)	C11—C12—C13	120.2 (2)
C10—N1—H1	116.00	C12—C13—C14	120.5 (3)
C9—N1—H1	116.00	C13—C14—C15	120.0 (3)
C2—C1—C7	122.95 (15)	C10—C15—C14	119.7 (2)
C2—C1—C6	118.88 (17)	C1—C2—H2	120.00
C6—C1—C7	118.16 (16)	C3—C2—H2	120.00
C1—C2—C3	120.18 (19)	C2—C3—H3	120.00
C2—C3—C4	120.3 (2)	C4—C3—H3	120.00
C3—C4—C5	120.0 (2)	C3—C4—H4	120.00
C4—C5—C6	120.4 (2)	C5—C4—H4	120.00
C1—C6—C5	120.3 (2)	C4—C5—H5	120.00
O1—C7—C1	122.07 (15)	C6—C5—H5	120.00
O1—C7—C8	118.58 (15)	C1—C6—H6	120.00
C1—C7—C8	119.35 (14)	C5—C6—H6	120.00
S1—C8—C7	110.07 (12)	S1—C8—H8	108.00
C7—C8—C9	111.48 (13)	C7—C8—H8	108.00
S1—C8—C9	112.26 (12)	C9—C8—H8	108.00
O2—C9—C8	119.05 (16)	C11—C12—H12	120.00
N1—C9—C8	119.09 (15)	C13—C12—H12	120.00
O2—C9—N1	121.86 (15)	C12—C13—H13	120.00
C11—C10—C15	120.25 (18)	C14—C13—H13	120.00
N1—C10—C11	120.91 (17)	C13—C14—H14	120.00
N1—C10—C15	118.82 (16)	C15—C14—H14	120.00
C10—C11—C12	119.31 (19)	C10—C15—H15	120.00
S1—C11—C10	120.12 (15)	C14—C15—H15	120.00

C11—S1—C8—C7	76.58 (13)	O1—C7—C8—S1	−99.48 (17)
C11—S1—C8—C9	−48.23 (14)	O1—C7—C8—C9	25.8 (2)
C8—S1—C11—C10	35.41 (16)	C1—C7—C8—S1	80.43 (18)
C8—S1—C11—C12	−149.38 (18)	C1—C7—C8—C9	−154.32 (16)
C10—N1—C9—O2	−177.54 (17)	S1—C8—C9—O2	−144.64 (15)
C10—N1—C9—C8	2.4 (3)	S1—C8—C9—N1	35.38 (19)
C9—N1—C10—C11	−20.1 (3)	C7—C8—C9—O2	91.3 (2)
C9—N1—C10—C15	161.39 (17)	C7—C8—C9—N1	−88.65 (19)
C6—C1—C2—C3	−1.3 (3)	N1—C10—C11—S1	−5.5 (2)
C7—C1—C2—C3	177.2 (2)	N1—C10—C11—C12	179.22 (19)
C2—C1—C6—C5	0.7 (3)	C15—C10—C11—S1	172.94 (14)
C7—C1—C6—C5	−177.9 (2)	C15—C10—C11—C12	−2.3 (3)
C2—C1—C7—O1	179.82 (18)	N1—C10—C15—C14	179.28 (19)
C2—C1—C7—C8	−0.1 (3)	C11—C10—C15—C14	0.8 (3)
C6—C1—C7—O1	−1.7 (3)	S1—C11—C12—C13	−173.2 (2)
C6—C1—C7—C8	178.41 (19)	C10—C11—C12—C13	2.1 (3)
C1—C2—C3—C4	0.9 (4)	C11—C12—C13—C14	−0.4 (4)
C2—C3—C4—C5	0.1 (4)	C12—C13—C14—C15	−1.2 (4)
C3—C4—C5—C6	−0.7 (4)	C13—C14—C15—C10	1.0 (4)
C4—C5—C6—C1	0.3 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱⁱⁱ	0.86	1.98	2.8383 (19)	179
C2—H2···O1ⁱ	0.93	2.55	3.453 (2)	165
C8—H8···O1ⁱ	0.98	2.36	3.170 (2)	140

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁NO₂S
M_r	269.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.1323 (3), 15.2893 (4), 10.5214 (4)
β (°)	114.669 (1)
V (Å³)	1334.99 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.25 × 0.20 × 0.10

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.939, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	10387, 2399, 2064
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.103, 1.04
No. of reflections	2399
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.41

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	1.98	2.8383 (19)	179
C2—H2···O1ⁱⁱ	0.93	2.55	3.453 (2)	165
C8—H8···O1ⁱⁱ	0.98	2.36	3.170 (2)	140

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

Acknowledgements

DS is grateful to the Higher Education Commission (Pakistan) for funding of this project and Professor Dr Islam Ullah Khan for providing research facilities at Government College University, Lahore, Pakistan.

References

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