Methyl 4-hy­droxy-2-isopropyl-1,1-dioxo-2H-1,2-benzothia­zine-3-carboxyl­ate

Arshad, M.N.; Khan, I.U.; Zia-ur-Rehman, M.; Rafique, H.M.; Holman, K.T.

doi:10.1107/S1600536811024573

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages o1823-o1824

doi:10.1107/S1600536811024573

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Methyl 4-hydroxy-2-isopropyl-1,1-dioxo-2H-1,2-benzothiazine-3-carboxylate

Muhammad Nadeem Arshad,^a ^*‡ Islam Ullah Khan,^b Muhammad Zia-ur-Rehman,^c H. M. Rafique ^a and K. Travis Holman ^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 Center, PCSIR Laboratories Complex, Ferozpur Road, Lahore 54600, Pakistan, and ^dDepartment of Chemistry, Georgetown University, 37th and Oth St NW, Washington DC 20057, USA
^*Correspondence e-mail: mnachemist@hotmail.com

(Received 14 June 2011; accepted 22 June 2011; online 25 June 2011)

In the crystal structure of the title molecule, C₁₃H₁₅NO₅S, the S and N atoms of the thiazine ring exihibit the maximum deviations from the least-squares plane of 0.3008 (6) and 0.3280 (7) Å, respectively. The ring therefore adopts a half chair conformation. The thiazine ring is twisted by an angle of 13.29 (7)° with respect to the aromatic ring. The isopropyl substituent is oriented at a dihedral angle of 53.2 (12)° with respect to the thiazine ring. An intramolecular O—H⋯O hydrogen bond occurs. Intermolecular hydrogen bonding is observed in the crystal structure.

Related literature

For the synthetic procedure, see: Arshad et al. (2011 ). For the biological activity of related compounds, see: Lombardino et al. (1971 ); Vidal et al. (2006 ); Turck et al. (1996); Zia-ur-Rehman et al. (2006 ). For related structures, see: Arshad et al. (2008 , 2009 ). For graph-set analysis, see Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₃H₁₅NO₅S
M_r = 297.32
Monoclinic, P 2₁ /n
a = 11.3896 (6) Å
b = 9.8421 (5) Å
c = 12.7680 (7) Å
β = 105.782 (1)°
V = 1377.31 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.43 × 0.27 × 0.27 mm

Data collection

Siemens SMART 1K diffractometer with a Bruker APEXII detector
Absorption correction: multi-scan (SADABS; Bruker 2001 ) T_min = 0.899, T_max = 0.949
16137 measured reflections
3380 independent reflections
2967 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.092
S = 1.06
3380 reflections
187 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2ⁱ	0.93	2.49	3.311 (2)	147
C3—H3⋯O2ⁱⁱ	0.93	2.46	3.370 (2)	165
C11—H11⋯O1ⁱⁱⁱ	0.98	2.39	3.317 (2)	157
O3—H3O⋯O4	0.88 (2)	1.77 (2)	2.578 (2)	151 (2)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (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 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811024573/im2299sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024573/im2299Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024573/im2299Isup3.cml

checkCIF report

Comment top

Benzothiazine 1,1-dioxide derivatives are the constituents of various drugs including Piroxicam and Meloxicam which are being used as non-steroidal anti-inflammatory drugs (NSAIDs) (Lombardino et al., 1971; Turck et al., 1996). Besides other biological activities (Zia-ur-Rehman et al., 2006) these type of molecules have found their applications as intermediates (Vidal et al., 2006). Our research group already reported the synthesis, biological activities (Arshad et al., 2011) and crystal structures (Arshad et al., 2008; 2009) of benzothiazine derivatives, II and III.

The title compound, I, is varied in structure with respect to III only concerning the alkyl group attached to the nitrogen atom of the thiazine ring. The characteristic intramolecular O—H···O hydrogen bond is observed in the structure of I as for II and III forming a six membered S¹₁(6) ring (C7/C8/C9/O4 H3O/O3) system (Bernstein, et al., 1995). The observed ring is inclined at dihedral angles of 18.9 (4)° and 16.1 (4)° with respect to the thiazine (C1/C6/C7/C8/N1/S1) and aromatic (C1/C2/C3/C4/C5/C6) rings. The isopropyl group is oriented at a dihedral angle of 53.2 (1)° relative to the thiazine ring. The dihedral angle between the thiazine and aromatic ring is 13.29 (7)°. Alongwith the O—H···O type hydrogen bonding interaction the molecule is connected to it's neighboring symmetry equivalents by additional weak C—H···O type interactions producing a three dimensional network (Fig. 2. Tab. 1).

Related literature top

For the synthetic procedure, see: Arshad et al. (2011); For the biological activity of related compounds, see: Lombardino et al. (1971); Vidal et al. (2006); Turck et al. (1996); Zia-ur-Rehman et al. (2006). For related structures, see: Arshad et al. (2008, 2009). For graph-set analysis, see Bernstein et al. (1995).

Experimental top

The synthesis of the titled compound has already been published (Arshad et al., 2011). Recrystallization from methanol under slow evaporation of the solvent leads to the formation of crystals suitable for structural analysis.

Computing details top

Data collection: APEX2 (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 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Ortep diagram for (I), thermal ellipsoids are drawn at the 50% probability level.
	Fig. 2. Unit cell packing for (I) showing hydrogen bonds as dashed lines. Hydrogen atoms not involved in hydrogen bonding interactions have been omitted.

Methyl 4-hydroxy-2-isopropyl-1,1-dioxo-2H-1,2-benzothiazine-3-carboxylate top

Crystal data top

C₁₃H₁₅NO₅S	F(000) = 624
M_r = 297.32	D_x = 1.434 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7059 reflections
a = 11.3896 (6) Å	θ = 2.7–28.4°
b = 9.8421 (5) Å	µ = 0.25 mm⁻¹
c = 12.7680 (7) Å	T = 100 K
β = 105.782 (1)°	Needle, colorless
V = 1377.31 (13) Å³	0.43 × 0.27 × 0.27 mm
Z = 4

Data collection top

Siemens SMART 1K diffractometer with a Bruker APEXII detector	3380 independent reflections
Radiation source: fine-focus sealed tube	2967 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker 2001)	h = −15→15
T_min = 0.899, T_max = 0.949	k = −13→12
16137 measured reflections	l = −16→16

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0464P)² + 0.6953P] where P = (F_o² + 2F_c²)/3
3380 reflections	(Δ/σ)_max < 0.001
187 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₃H₁₅NO₅S	V = 1377.31 (13) Å³
M_r = 297.32	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.3896 (6) Å	µ = 0.25 mm⁻¹
b = 9.8421 (5) Å	T = 100 K
c = 12.7680 (7) Å	0.43 × 0.27 × 0.27 mm
β = 105.782 (1)°

Data collection top

Siemens SMART 1K diffractometer with a Bruker APEXII detector	3380 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2001)	2967 reflections with I > 2σ(I)
T_min = 0.899, T_max = 0.949	R_int = 0.024
16137 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.43 e Å⁻³
3380 reflections	Δρ_min = −0.40 e Å⁻³
187 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	0.45158 (3)	0.80155 (3)	0.24103 (3)	0.01449 (10)
O1	0.41963 (9)	0.73289 (10)	0.32827 (8)	0.0204 (2)
O2	0.46334 (9)	0.72358 (10)	0.14956 (8)	0.0208 (2)
O4	0.32490 (9)	1.14730 (11)	−0.03579 (8)	0.0239 (2)
O5	0.19108 (9)	1.00457 (10)	0.00818 (8)	0.0206 (2)
O3	0.54813 (10)	1.14548 (11)	0.08196 (9)	0.0235 (2)
N1	0.35223 (10)	0.92191 (11)	0.19471 (9)	0.0148 (2)
C1	0.58852 (11)	0.89070 (13)	0.29337 (10)	0.0144 (2)
C2	0.67716 (12)	0.84231 (14)	0.38274 (11)	0.0167 (3)
H2	0.6646	0.7626	0.4174	0.020*
C3	0.78531 (12)	0.91527 (15)	0.41972 (11)	0.0194 (3)
H3	0.8463	0.8834	0.4788	0.023*
C4	0.80243 (13)	1.03493 (15)	0.36896 (12)	0.0213 (3)
H4	0.8745	1.0835	0.3950	0.026*
C5	0.71319 (13)	1.08340 (15)	0.27951 (11)	0.0207 (3)
H5	0.7258	1.1639	0.2459	0.025*
C6	0.60455 (12)	1.01095 (14)	0.24018 (11)	0.0163 (3)
C7	0.50866 (12)	1.05859 (14)	0.14559 (11)	0.0171 (3)
C8	0.39091 (12)	1.01442 (13)	0.12351 (11)	0.0159 (3)
C9	0.30108 (12)	1.06172 (14)	0.02519 (11)	0.0180 (3)
C10	0.09884 (14)	1.05700 (17)	−0.08516 (12)	0.0271 (3)
H10A	0.0828	1.1505	−0.0728	0.041*
H10B	0.0252	1.0051	−0.0954	0.041*
H10C	0.1276	1.0500	−0.1490	0.041*
C11	0.28252 (12)	0.98889 (14)	0.26547 (11)	0.0181 (3)
H11	0.2354	1.0621	0.2214	0.022*
C13	0.36474 (14)	1.05728 (17)	0.36523 (12)	0.0258 (3)
H13A	0.4031	0.9894	0.4173	0.039*
H13B	0.3170	1.1166	0.3970	0.039*
H13C	0.4262	1.1091	0.3444	0.039*
C12	0.18920 (13)	0.89440 (17)	0.29256 (13)	0.0263 (3)
H12A	0.1452	0.8473	0.2280	0.039*
H12B	0.1332	0.9466	0.3205	0.039*
H12C	0.2303	0.8297	0.3464	0.039*
H3O	0.482 (2)	1.167 (2)	0.0300 (17)	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01430 (16)	0.01178 (16)	0.01607 (17)	0.00005 (11)	0.00187 (12)	0.00036 (11)
O1	0.0185 (5)	0.0178 (5)	0.0237 (5)	−0.0013 (4)	0.0035 (4)	0.0067 (4)
O2	0.0194 (5)	0.0180 (5)	0.0225 (5)	0.0020 (4)	0.0015 (4)	−0.0060 (4)
O4	0.0277 (5)	0.0229 (5)	0.0188 (5)	0.0008 (4)	0.0023 (4)	0.0069 (4)
O5	0.0186 (5)	0.0226 (5)	0.0176 (5)	0.0017 (4)	−0.0002 (4)	0.0023 (4)
O3	0.0259 (5)	0.0252 (5)	0.0178 (5)	−0.0055 (4)	0.0033 (4)	0.0078 (4)
N1	0.0158 (5)	0.0139 (5)	0.0145 (5)	0.0027 (4)	0.0041 (4)	0.0021 (4)
C1	0.0147 (6)	0.0149 (6)	0.0138 (6)	−0.0013 (5)	0.0043 (5)	−0.0027 (5)
C2	0.0189 (6)	0.0158 (6)	0.0157 (6)	0.0011 (5)	0.0055 (5)	0.0003 (5)
C3	0.0172 (6)	0.0237 (7)	0.0157 (6)	0.0019 (5)	0.0020 (5)	−0.0018 (5)
C4	0.0175 (6)	0.0252 (7)	0.0205 (7)	−0.0058 (5)	0.0042 (5)	−0.0036 (6)
C5	0.0225 (7)	0.0209 (7)	0.0190 (7)	−0.0056 (5)	0.0063 (5)	0.0019 (5)
C6	0.0179 (6)	0.0180 (6)	0.0134 (6)	−0.0011 (5)	0.0048 (5)	−0.0003 (5)
C7	0.0228 (7)	0.0153 (6)	0.0137 (6)	−0.0013 (5)	0.0054 (5)	0.0003 (5)
C8	0.0199 (6)	0.0142 (6)	0.0133 (6)	0.0006 (5)	0.0037 (5)	0.0007 (5)
C9	0.0214 (6)	0.0160 (6)	0.0161 (6)	0.0020 (5)	0.0040 (5)	−0.0008 (5)
C10	0.0232 (7)	0.0304 (8)	0.0220 (7)	0.0037 (6)	−0.0036 (6)	0.0038 (6)
C11	0.0191 (6)	0.0181 (6)	0.0182 (7)	0.0042 (5)	0.0072 (5)	0.0004 (5)
C13	0.0286 (8)	0.0290 (8)	0.0211 (7)	0.0014 (6)	0.0091 (6)	−0.0053 (6)
C12	0.0212 (7)	0.0291 (8)	0.0314 (8)	0.0017 (6)	0.0117 (6)	0.0037 (6)

Geometric parameters (Å, º) top

S1—O1	1.4319 (10)	C4—H4	0.9300
S1—O2	1.4338 (10)	C5—C6	1.3978 (19)
S1—N1	1.6338 (11)	C5—H5	0.9300
S1—C1	1.7556 (13)	C6—C7	1.4675 (18)
O4—C9	1.2264 (17)	C7—C8	1.3644 (19)
O5—C9	1.3361 (17)	C8—C9	1.4632 (18)
O5—C10	1.4524 (16)	C10—H10A	0.9600
O3—C7	1.3387 (16)	C10—H10B	0.9600
O3—H3O	0.88 (2)	C10—H10C	0.9600
N1—C8	1.4378 (17)	C11—C13	1.518 (2)
N1—C11	1.5072 (16)	C11—C12	1.521 (2)
C1—C2	1.3862 (18)	C11—H11	0.9800
C1—C6	1.4009 (18)	C13—H13A	0.9600
C2—C3	1.3926 (19)	C13—H13B	0.9600
C2—H2	0.9300	C13—H13C	0.9600
C3—C4	1.383 (2)	C12—H12A	0.9600
C3—H3	0.9300	C12—H12B	0.9600
C4—C5	1.390 (2)	C12—H12C	0.9600

O1—S1—O2	118.74 (6)	C8—C7—C6	122.54 (12)
O1—S1—N1	109.04 (6)	C7—C8—N1	121.61 (12)
O2—S1—N1	107.59 (6)	C7—C8—C9	119.64 (12)
O1—S1—C1	109.10 (6)	N1—C8—C9	118.75 (11)
O2—S1—C1	107.90 (6)	O4—C9—O5	123.06 (12)
N1—S1—C1	103.39 (6)	O4—C9—C8	122.64 (13)
C9—O5—C10	114.88 (11)	O5—C9—C8	114.29 (12)
C7—O3—H3O	104.6 (14)	O5—C10—H10A	109.5
C8—N1—C11	113.82 (10)	O5—C10—H10B	109.5
C8—N1—S1	112.76 (9)	H10A—C10—H10B	109.5
C11—N1—S1	121.74 (9)	O5—C10—H10C	109.5
C2—C1—C6	121.84 (12)	H10A—C10—H10C	109.5
C2—C1—S1	120.95 (10)	H10B—C10—H10C	109.5
C6—C1—S1	117.20 (10)	N1—C11—C13	113.06 (11)
C1—C2—C3	118.74 (13)	N1—C11—C12	112.55 (11)
C1—C2—H2	120.6	C13—C11—C12	112.96 (12)
C3—C2—H2	120.6	N1—C11—H11	105.8
C4—C3—C2	120.30 (13)	C13—C11—H11	105.8
C4—C3—H3	119.8	C12—C11—H11	105.8
C2—C3—H3	119.8	C11—C13—H13A	109.5
C3—C4—C5	120.81 (13)	C11—C13—H13B	109.5
C3—C4—H4	119.6	H13A—C13—H13B	109.5
C5—C4—H4	119.6	C11—C13—H13C	109.5
C4—C5—C6	119.86 (13)	H13A—C13—H13C	109.5
C4—C5—H5	120.1	H13B—C13—H13C	109.5
C6—C5—H5	120.1	C11—C12—H12A	109.5
C5—C6—C1	118.43 (12)	C11—C12—H12B	109.5
C5—C6—C7	121.37 (12)	H12A—C12—H12B	109.5
C1—C6—C7	120.19 (12)	C11—C12—H12C	109.5
O3—C7—C8	123.48 (12)	H12A—C12—H12C	109.5
O3—C7—C6	113.95 (12)	H12B—C12—H12C	109.5

O1—S1—N1—C8	167.45 (9)	C5—C6—C7—O3	20.73 (19)
O2—S1—N1—C8	−62.53 (10)	C1—C6—C7—O3	−159.37 (12)
C1—S1—N1—C8	51.48 (10)	C5—C6—C7—C8	−161.14 (13)
O1—S1—N1—C11	26.69 (11)	C1—C6—C7—C8	18.8 (2)
O2—S1—N1—C11	156.70 (10)	O3—C7—C8—N1	−179.43 (12)
C1—S1—N1—C11	−89.28 (11)	C6—C7—C8—N1	2.6 (2)
O1—S1—C1—C2	31.83 (13)	O3—C7—C8—C9	0.6 (2)
O2—S1—C1—C2	−98.46 (12)	C6—C7—C8—C9	−177.37 (12)
N1—S1—C1—C2	147.76 (11)	C11—N1—C8—C7	102.87 (14)
O1—S1—C1—C6	−149.00 (10)	S1—N1—C8—C7	−41.11 (16)
O2—S1—C1—C6	80.71 (11)	C11—N1—C8—C9	−77.14 (15)
N1—S1—C1—C6	−33.07 (11)	S1—N1—C8—C9	138.88 (11)
C6—C1—C2—C3	−0.5 (2)	C10—O5—C9—O4	−3.37 (19)
S1—C1—C2—C3	178.64 (10)	C10—O5—C9—C8	176.14 (12)
C1—C2—C3—C4	1.1 (2)	C7—C8—C9—O4	−4.9 (2)
C2—C3—C4—C5	−0.9 (2)	N1—C8—C9—O4	175.11 (12)
C3—C4—C5—C6	0.1 (2)	C7—C8—C9—O5	175.59 (12)
C4—C5—C6—C1	0.5 (2)	N1—C8—C9—O5	−4.40 (18)
C4—C5—C6—C7	−179.64 (13)	C8—N1—C11—C13	−80.86 (14)
C2—C1—C6—C5	−0.3 (2)	S1—N1—C11—C13	59.52 (15)
S1—C1—C6—C5	−179.45 (10)	C8—N1—C11—C12	149.66 (12)
C2—C1—C6—C7	179.81 (12)	S1—N1—C11—C12	−69.95 (14)
S1—C1—C6—C7	0.65 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.93	2.49	3.311 (2)	147
C3—H3···O2ⁱⁱ	0.93	2.46	3.370 (2)	165
C11—H11···O1ⁱⁱⁱ	0.98	2.39	3.317 (2)	157
O3—H3O···O4	0.88 (2)	1.77 (2)	2.578 (2)	151 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₅NO₅S
M_r	297.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	11.3896 (6), 9.8421 (5), 12.7680 (7)
β (°)	105.782 (1)
V (Å³)	1377.31 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.43 × 0.27 × 0.27

Data collection
Diffractometer	Siemens SMART 1K diffractometer with a Bruker APEXII detector
Absorption correction	Multi-scan (SADABS; Bruker 2001)
T_min, T_max	0.899, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	16137, 3380, 2967
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.06
No. of reflections	3380
No. of parameters	187
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.40

Computer programs: APEX2 (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (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
C4—H4···O2ⁱ	0.93	2.49	3.311 (2)	147
C3—H3···O2ⁱⁱ	0.93	2.46	3.370 (2)	165
C11—H11···O1ⁱⁱⁱ	0.98	2.39	3.317 (2)	157
O3—H3O···O4	0.88 (2)	1.77 (2)	2.578 (2)	151 (2)

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

Footnotes

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

Acknowledgements

The authors acknowledge the Higher Education Commission of Pakistan for providing fellowships to MNA (PIN # 042-120607-Ps2-183 & PIN # IRSIP-10-PS-2).

References

Arshad, M. N., Khan, I. U., Zia-ur-Rehman, M. & Shafiq, M. (2011). Asian J. Chem. 23, 2801–2805. CAS Google Scholar
Arshad, M. N., Tahir, M. N., Khan, I. U., Shafiq, M. & Siddiqui, W. A. (2008). Acta Cryst. E64, o2045. Web of Science CSD CrossRef IUCr Journals Google Scholar
Arshad, M. N., Zia-ur-Rehman, M. & Khan, I. U. (2009). Acta Cryst. E65, o3077. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2001). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Lombardino, J. G., Wiseman, E. H. & McLamore, W. (1971). J. Med. Chem. 14, 1171–1175. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Turck, D., Busch, U., Heinzel, G., Narjes, H. & Nehmiz, G. (1996). J. Clin. Pharmacol. 36, 79–84. PubMed Web of Science Google Scholar
Vidal, A., Madelmont, J. C. & Mounetou, E. (2006). Synthesis, pp. 591–594. CrossRef Google Scholar
Zia-ur-Rehman, M., Anwar, J., Ahmad, S. & &Siddiqui, H. L. (2006). Chem. Pharm. Bull. 54, 1175–1178. Web of Science PubMed CAS Google Scholar