Methyl 2-benzyl-4-hy­droxy-1,1-dioxo-1,2,3,4-tetra­hydro-1λ6,2-benzothia­zine-3-carboxyl­ate

Arshad, M.N.; Khan, I.U.; Zia-ur-Rehman, M.; Shafiq, M.; Asiri, A.M.

doi:10.1107/S1600536811020289

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages o1588-o1589

doi:10.1107/S1600536811020289

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Methyl 2-benzyl-4-hydroxy-1,1-dioxo-1,2,3,4-tetrahydro-1λ⁶,2-benzothiazine-3-carboxylate

Muhammad Nadeem Arshad,^a ^*‡ Islam Ullah Khan,^b Muhammad Zia-ur-Rehman,^c Muhammad Shafiq ^b and Abdullah M. Asiri ^d

^aX-ray Diffraction and Crystallography Laboratory, Department of Physics, School of Physical Sciences, University of the Punjab, Quaid-e-Azam Campus, Lahore 54590, Pakistan, ^bMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, ^cApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, Pakistan, and ^dThe Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah, PO Box 80203, Saudi Arabia
^*Correspondence e-mail: mnachemist@hotmail.com

(Received 25 May 2011; accepted 27 May 2011; online 4 June 2011)

In the title compound, C₁₇H₁₅NO₅S, the benzene ring of the fused-ring system is twisted by 11.67 (6)° with respect to the thiazine ring. The atoms of the four-atom methyl ester group and the phenyl ring of the benzyl unit are inclined at 16.50 (7) and 44.52 (3)° with respect to the thiazine ring. An intramolecular O—H⋯O hydrogen bond gives rise to a six-membered S(6) ring motif. In the crystal, molecules are extended through a C—H⋯O interaction along the a axis. C—H⋯π interactions are also observed.

Related literature

For the biological properties of benzothiazines, see: Zia-ur-Rehman et al. (2005 , 2006 ). For a related structure, see: Arshad et al. (2009 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₇H₁₅NO₅S
M_r = 345.36
Monoclinic, P 2₁ /c
a = 9.4920 (15) Å
b = 10.9607 (17) Å
c = 15.050 (2) Å
β = 99.758 (2)°
V = 1543.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.43 × 0.25 × 0.19 mm

Data collection

Bruker SMART 1K diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.905, T_max = 0.956
13430 measured reflections
3719 independent reflections
3297 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 1.06
3719 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O4ⁱ	0.95	2.49	3.1861 (19)	130
O1—H1O⋯O4	0.93 (2)	1.72 (2)	2.5580 (15)	149 (2)
C10—H10B⋯Cg1ⁱⁱ	0.80	2.94	3.6391 (18)	130
Symmetry codes: (i) x+1, y, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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: X-SEED (Barbour, 2001), WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020289/ng5172sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020289/ng5172Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020289/ng5172Isup3.cml

checkCIF report

Comment top

Crystallographic and biological studies of benzothiazine molecules and their derivatives gained much attraction in recent literature (Zia-ur-Rehman et al. 2005, 2006) and (Arshad et al. 2009).

The title compound is N-alkylated derivative of methyl -4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide. The methyl ester moiety attached to the thiazine ring is almost planer showing the r. m. s. deviation of 0.0087Å and is oriented at dihedral angle of 16.50 (7)° with respect to the thiazine ring. The typical intramolecular O–H···O interaction of 4-hydroxy benzothiazine molecules observed and generates almost planer six membered ring motif S₁¹(6)(Bernstein, et al., 1995) with the r.m.s deviaton of 0.0085Å and produces dihedral angles of 16.02 (33)° & 15.87 (32)° with respect to the thiazine and aromatic (C1/C2/C3/C4/C5/C6) rings respectively. The thiazine ring adopted the half chair shaped as the S1 and N1 showed maximum deviation from the least square plane measure 0.3113 (7)Å and 0.3082 (8)Å respectively and root mean square deviation for the ring is 0.2031Å. A weak intermolecular hydrogen bonding interaction observed along the a axes (Fig.2. Tab.1). Further hydrogen atom from methyl group of ester moiety involved in symmetry related C—H···.π interaction [C10—H10B···.Cg1, where Cg1 is centroid of (C1—C6)] table 1. The benzyl ring attached to nitogen atom of thiazine ring is oriented at dihedral angle of 51.33 (3)° and 44.52 (3)° with respect to the aromatic (C1—C6) and thiazine rings respectively.

Related literature top

For the biological properties of benzothiazines, see: Zia-ur-Rehman et al. (2005, 2006). For a related structure, see: Arshad et al. (2009). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

A mixture of methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide (350 mg, 1.37 mmol), sodium hydride (77 mg, 3.2 mmol) and dimethylformamide (5 ml) was prperaed in a round bottom flask. Benzyl Chloride (202 mg, 1.6 mmol) was added drop wise to the above mixture. Contents were allowed to stirr at room temperature for 5 h under nitrogen atmosphere and poured over ice cooled water (100 ml). The pH was adjusted 2-3 using 1N HCL which yielded precipetates . The precipitates were filtered, washed with cold water and dried. Single crystals were obtained by re-crystallization from a methanol solution under slow evaporation.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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: X-SEED (Barbour, 2001), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The labelled diagram of (I) with thermal ellipsoids drawn at 50% probability level.
	Fig. 2. Unit cell packing for (I) showinh the inter and intramolecular hydrogen bondings using dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

Methyl 2-benzyl-4-hydroxy-1,1-dioxo-1,2,3,4-tetrahydro-1λ⁶,2- benzothiazine-3-carboxylate top

Crystal data top

C₁₇H₁₅NO₅S	F(000) = 720
M_r = 345.36	D_x = 1.487 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 422 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.4920 (15) Å	Cell parameters from 6007 reflections
b = 10.9607 (17) Å	θ = 2.3–28.3°
c = 15.050 (2) Å	µ = 0.24 mm⁻¹
β = 99.758 (2)°	T = 173 K
V = 1543.1 (4) Å³	Block, colorless
Z = 4	0.43 × 0.25 × 0.19 mm

Data collection top

Bruker SMART 1K diffractometer	3719 independent reflections
Radiation source: fine-focus sealed tube	3297 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
T_min = 0.905, T_max = 0.956	k = −14→14
13430 measured reflections	l = −20→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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0721P)² + 0.6338P] where P = (F_o² + 2F_c²)/3
3719 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 0.79 e Å⁻³
0 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

C₁₇H₁₅NO₅S	V = 1543.1 (4) Å³
M_r = 345.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4920 (15) Å	µ = 0.24 mm⁻¹
b = 10.9607 (17) Å	T = 173 K
c = 15.050 (2) Å	0.43 × 0.25 × 0.19 mm
β = 99.758 (2)°

Data collection top

Bruker SMART 1K diffractometer	3719 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3297 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.956	R_int = 0.033
13430 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.79 e Å⁻³
3719 reflections	Δρ_min = −0.57 e Å⁻³
221 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 > 2σ(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	0.81488 (4)	0.52594 (3)	0.28570 (2)	0.01595 (12)
O4	0.30241 (11)	0.50771 (10)	0.17813 (7)	0.0183 (2)
C1	0.83777 (15)	0.56206 (13)	0.17521 (10)	0.0157 (3)
O1	0.46409 (11)	0.60454 (10)	0.07788 (7)	0.0187 (2)
C2	0.97337 (16)	0.58108 (14)	0.15447 (10)	0.0188 (3)
H2	1.0565	0.5666	0.1981	0.023*
O5	0.40378 (11)	0.40446 (10)	0.30203 (7)	0.0177 (2)
C3	0.98459 (17)	0.62175 (14)	0.06835 (11)	0.0209 (3)
H3	1.0763	0.6351	0.0529	0.025*
O2	0.93353 (11)	0.45544 (11)	0.33020 (7)	0.0220 (3)
C4	0.86248 (17)	0.64307 (14)	0.00470 (10)	0.0204 (3)
H4	0.8715	0.6726	−0.0534	0.025*
O3	0.77720 (12)	0.63674 (10)	0.32661 (7)	0.0211 (2)
C5	0.72758 (16)	0.62151 (13)	0.02546 (10)	0.0176 (3)
H5	0.6448	0.6353	−0.0185	0.021*
N1	0.67339 (13)	0.43784 (11)	0.26853 (8)	0.0156 (3)
C6	0.71401 (15)	0.57923 (13)	0.11162 (10)	0.0152 (3)
C7	0.57231 (15)	0.55402 (13)	0.13462 (10)	0.0153 (3)
C8	0.55400 (15)	0.48728 (13)	0.20867 (10)	0.0150 (3)
C9	0.40936 (16)	0.46801 (13)	0.22778 (10)	0.0154 (3)
C11	0.69172 (16)	0.30226 (13)	0.26997 (10)	0.0169 (3)
H11A	0.6125	0.2651	0.2957	0.020*
H11B	0.7821	0.2818	0.3105	0.020*
C12	0.69472 (16)	0.24606 (13)	0.17890 (10)	0.0165 (3)
C13	0.56919 (17)	0.20116 (14)	0.12780 (11)	0.0212 (3)
H13	0.4816	0.2081	0.1500	0.025*
C14	0.5710 (2)	0.14639 (16)	0.04476 (12)	0.0307 (4)
H14	0.4848	0.1168	0.0101	0.037*
C15	0.6992 (2)	0.13497 (16)	0.01245 (12)	0.0340 (4)
H15	0.7007	0.0970	−0.0441	0.041*
C16	0.8247 (2)	0.17886 (16)	0.06271 (12)	0.0308 (4)
H16	0.9123	0.1703	0.0408	0.037*
C10	0.26012 (16)	0.38959 (15)	0.32309 (11)	0.0199 (3)
H10A	0.2184	0.4700	0.3303	0.030*
H10B	0.2652	0.3431	0.3792	0.030*
H10C	0.2003	0.3456	0.2739	0.030*
C17	0.82300 (18)	0.23540 (14)	0.14515 (11)	0.0225 (3)
H17	0.9091	0.2669	0.1787	0.027*
H1O	0.381 (3)	0.583 (2)	0.0989 (14)	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01167 (19)	0.0206 (2)	0.0152 (2)	−0.00077 (12)	0.00123 (13)	0.00070 (13)
O4	0.0117 (5)	0.0229 (5)	0.0201 (5)	0.0010 (4)	0.0018 (4)	−0.0008 (4)
C1	0.0153 (7)	0.0163 (7)	0.0155 (7)	0.0000 (5)	0.0030 (5)	0.0000 (5)
O1	0.0134 (5)	0.0227 (6)	0.0193 (5)	0.0025 (4)	0.0007 (4)	0.0035 (4)
C2	0.0148 (7)	0.0206 (7)	0.0210 (7)	0.0001 (5)	0.0030 (5)	0.0004 (6)
O5	0.0134 (5)	0.0198 (5)	0.0207 (5)	0.0004 (4)	0.0051 (4)	0.0023 (4)
C3	0.0174 (7)	0.0230 (8)	0.0240 (8)	−0.0024 (6)	0.0085 (6)	−0.0010 (6)
O2	0.0121 (5)	0.0308 (6)	0.0219 (6)	0.0010 (4)	−0.0002 (4)	0.0060 (4)
C4	0.0236 (8)	0.0207 (7)	0.0181 (7)	−0.0009 (6)	0.0066 (6)	0.0007 (6)
O3	0.0199 (5)	0.0238 (6)	0.0196 (5)	−0.0038 (4)	0.0033 (4)	−0.0037 (4)
C5	0.0175 (7)	0.0179 (7)	0.0169 (7)	0.0004 (5)	0.0015 (5)	−0.0009 (5)
N1	0.0122 (6)	0.0165 (6)	0.0178 (6)	0.0004 (4)	0.0018 (5)	0.0015 (5)
C6	0.0147 (7)	0.0142 (7)	0.0169 (7)	0.0005 (5)	0.0030 (5)	−0.0012 (5)
C7	0.0136 (7)	0.0152 (6)	0.0169 (7)	0.0013 (5)	0.0018 (5)	−0.0021 (5)
C8	0.0119 (7)	0.0149 (7)	0.0176 (7)	0.0016 (5)	0.0010 (5)	−0.0008 (5)
C9	0.0153 (7)	0.0137 (7)	0.0172 (7)	−0.0004 (5)	0.0028 (5)	−0.0028 (5)
C11	0.0161 (7)	0.0174 (7)	0.0173 (7)	0.0025 (5)	0.0028 (5)	0.0033 (5)
C12	0.0178 (7)	0.0134 (7)	0.0186 (7)	0.0017 (5)	0.0039 (5)	0.0031 (5)
C13	0.0195 (7)	0.0174 (7)	0.0250 (8)	0.0022 (6)	−0.0012 (6)	0.0029 (6)
C14	0.0420 (10)	0.0189 (8)	0.0259 (8)	0.0036 (7)	−0.0092 (7)	0.0020 (6)
C15	0.0651 (13)	0.0198 (8)	0.0181 (8)	0.0076 (8)	0.0103 (8)	0.0023 (6)
C16	0.0448 (11)	0.0209 (8)	0.0330 (9)	0.0054 (7)	0.0244 (8)	0.0064 (7)
C10	0.0140 (7)	0.0219 (8)	0.0249 (8)	−0.0017 (5)	0.0066 (6)	0.0006 (6)
C17	0.0228 (8)	0.0185 (7)	0.0286 (8)	−0.0006 (6)	0.0110 (6)	0.0033 (6)

Geometric parameters (Å, º) top

S1—O3	1.4341 (12)	C6—C7	1.471 (2)
S1—O2	1.4347 (11)	C7—C8	1.369 (2)
S1—N1	1.6387 (13)	C8—C9	1.465 (2)
S1—C1	1.7583 (15)	C11—C12	1.507 (2)
O4—C9	1.2333 (18)	C11—H11A	0.9900
C1—C2	1.391 (2)	C11—H11B	0.9900
C1—C6	1.397 (2)	C12—C13	1.394 (2)
O1—C7	1.3393 (17)	C12—C17	1.401 (2)
O1—H1O	0.93 (2)	C13—C14	1.389 (2)
C2—C3	1.392 (2)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.391 (3)
O5—C9	1.3254 (18)	C14—H14	0.9500
O5—C10	1.4606 (17)	C15—C16	1.384 (3)
C3—C4	1.393 (2)	C15—H15	0.9500
C3—H3	0.9500	C16—C17	1.389 (2)
C4—C5	1.389 (2)	C16—H16	0.9500
C4—H4	0.9500	C10—H10A	0.9800
C5—C6	1.403 (2)	C10—H10B	0.9800
C5—H5	0.9500	C10—H10C	0.9800
N1—C8	1.4295 (18)	C17—H17	0.9500
N1—C11	1.4959 (19)

O3—S1—O2	119.27 (7)	N1—C8—C9	119.40 (13)
O3—S1—N1	108.02 (6)	O4—C9—O5	123.35 (13)
O2—S1—N1	108.29 (7)	O4—C9—C8	122.20 (13)
O3—S1—C1	107.16 (7)	O5—C9—C8	114.46 (13)
O2—S1—C1	110.47 (7)	N1—C11—C12	114.38 (12)
N1—S1—C1	102.29 (7)	N1—C11—H11A	108.7
C2—C1—C6	121.94 (13)	C12—C11—H11A	108.7
C2—C1—S1	120.90 (11)	N1—C11—H11B	108.7
C6—C1—S1	117.00 (11)	C12—C11—H11B	108.7
C7—O1—H1O	106.1 (14)	H11A—C11—H11B	107.6
C1—C2—C3	118.48 (14)	C13—C12—C17	118.98 (14)
C1—C2—H2	120.8	C13—C12—C11	119.99 (13)
C3—C2—H2	120.8	C17—C12—C11	121.01 (14)
C9—O5—C10	114.45 (11)	C14—C13—C12	120.60 (15)
C2—C3—C4	120.55 (14)	C14—C13—H13	119.7
C2—C3—H3	119.7	C12—C13—H13	119.7
C4—C3—H3	119.7	C13—C14—C15	119.92 (17)
C5—C4—C3	120.55 (14)	C13—C14—H14	120.0
C5—C4—H4	119.7	C15—C14—H14	120.0
C3—C4—H4	119.7	C16—C15—C14	120.03 (16)
C4—C5—C6	119.77 (14)	C16—C15—H15	120.0
C4—C5—H5	120.1	C14—C15—H15	120.0
C6—C5—H5	120.1	C15—C16—C17	120.24 (16)
C8—N1—C11	117.62 (11)	C15—C16—H16	119.9
C8—N1—S1	114.65 (10)	C17—C16—H16	119.9
C11—N1—S1	119.53 (10)	O5—C10—H10A	109.5
C1—C6—C5	118.65 (13)	O5—C10—H10B	109.5
C1—C6—C7	120.66 (13)	H10A—C10—H10B	109.5
C5—C6—C7	120.68 (13)	O5—C10—H10C	109.5
O1—C7—C8	123.41 (13)	H10A—C10—H10C	109.5
O1—C7—C6	113.92 (12)	H10B—C10—H10C	109.5
C8—C7—C6	122.65 (13)	C16—C17—C12	120.22 (16)
C7—C8—N1	121.28 (13)	C16—C17—H17	119.9
C7—C8—C9	119.31 (13)	C12—C17—H17	119.9

O3—S1—C1—C2	98.81 (13)	O1—C7—C8—N1	−178.36 (13)
O2—S1—C1—C2	−32.60 (15)	C6—C7—C8—N1	0.0 (2)
N1—S1—C1—C2	−147.69 (13)	O1—C7—C8—C9	0.5 (2)
O3—S1—C1—C6	−76.69 (13)	C6—C7—C8—C9	178.95 (13)
O2—S1—C1—C6	151.90 (11)	C11—N1—C8—C7	−111.02 (15)
N1—S1—C1—C6	36.80 (13)	S1—N1—C8—C7	37.42 (17)
C6—C1—C2—C3	1.9 (2)	C11—N1—C8—C9	70.08 (17)
S1—C1—C2—C3	−173.42 (11)	S1—N1—C8—C9	−141.49 (11)
C1—C2—C3—C4	0.1 (2)	C10—O5—C9—O4	−2.7 (2)
C2—C3—C4—C5	−1.4 (2)	C10—O5—C9—C8	177.58 (12)
C3—C4—C5—C6	0.7 (2)	C7—C8—C9—O4	1.7 (2)
O3—S1—N1—C8	61.81 (11)	N1—C8—C9—O4	−179.41 (13)
O2—S1—N1—C8	−167.73 (10)	C7—C8—C9—O5	−178.62 (13)
C1—S1—N1—C8	−51.05 (11)	N1—C8—C9—O5	0.31 (19)
O3—S1—N1—C11	−150.40 (10)	C8—N1—C11—C12	54.00 (17)
O2—S1—N1—C11	−19.94 (13)	S1—N1—C11—C12	−92.85 (14)
C1—S1—N1—C11	96.74 (11)	N1—C11—C12—C13	−93.63 (16)
C2—C1—C6—C5	−2.5 (2)	N1—C11—C12—C17	87.87 (17)
S1—C1—C6—C5	172.92 (11)	C17—C12—C13—C14	0.1 (2)
C2—C1—C6—C7	177.73 (14)	C11—C12—C13—C14	−178.38 (14)
S1—C1—C6—C7	−6.82 (19)	C12—C13—C14—C15	0.6 (2)
C4—C5—C6—C1	1.2 (2)	C13—C14—C15—C16	−0.4 (3)
C4—C5—C6—C7	−179.06 (14)	C14—C15—C16—C17	−0.6 (3)
C1—C6—C7—O1	162.79 (13)	C15—C16—C17—C12	1.4 (2)
C5—C6—C7—O1	−16.94 (19)	C13—C12—C17—C16	−1.2 (2)
C1—C6—C7—C8	−15.8 (2)	C11—C12—C17—C16	177.36 (14)
C5—C6—C7—C8	164.52 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4ⁱ	0.95	2.49	3.1861 (19)	130
O1—H1O···O4	0.93 (2)	1.72 (2)	2.5580 (15)	149 (2)
C10—H10B···Cg1ⁱⁱ	0.80	2.94	3.6391 (18)	130

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅NO₅S
M_r	345.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	9.4920 (15), 10.9607 (17), 15.050 (2)
β (°)	99.758 (2)
V (Å³)	1543.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.43 × 0.25 × 0.19

Data collection
Diffractometer	Bruker SMART 1K diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.905, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	13430, 3719, 3297
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 1.06
No. of reflections	3719
No. of parameters	221
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.57

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), X-SEED (Barbour, 2001), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4ⁱ	0.95	2.49	3.1861 (19)	130
O1—H1O···O4	0.93 (2)	1.72 (2)	2.5580 (15)	149 (2)
C10—H10B···Cg1ⁱⁱ	0.8017	2.94	3.6391 (18)	130

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

Footnotes

‡Current address: Materials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan.

Acknowledgements

MNA acknowledges the HEC for providing a Fellowship under the International Research Support Initiative Program (IRSIP)

References

Arshad, M. N., Zia-ur-Rehman, M. & Khan, I. U. (2009). Acta Cryst. E65, o3077. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 67| Part 7| July 2011| Pages o1588-o1589

doi:10.1107/S1600536811020289

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