Methyl 2-acetonyl-4-hydr­oxy-2H-1,2-benzothia­zine-3-carboxyl­ate 1,1-dioxide

Ahmad, M.; Latif Siddiqui, H.; Zia-ur-Rehman, M.; Tizzard, G.J.; Ahmad, S.

doi:10.1107/S1600536808019156

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1392

doi:10.1107/S1600536808019156

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Methyl 2-acetonyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Matloob Ahmad,^a ^* Hamid Latif Siddiqui,^a Muhammad Zia-ur-Rehman,^b Graham John Tizzard ^c and Saeed Ahmad ^d

^aInstitute of Chemistry, University of The Punjab, Lahore 54590, Pakistan, ^bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, Pakistan, ^cSchool of Chemistry, University of Southampton, England, and ^dChemistry Department, University of Science and Technology, Bannu, Pakistan
^*Correspondence e-mail: matloob_123@yahoo.com

(Received 19 June 2008; accepted 24 June 2008; online 5 July 2008)

In the molecule of the title compound, C₁₃H₁₃NO₆S, the thiazine ring adopts a distorted sofa conformation. The enolic H atom is involved in intramolecular O—H⋯O hydrogen bonding besides the weaker C—H⋯O=S and C—H⋯O=C interactions.

Related literature

For related literature, see: Ahmad et al. (2008 ); Zia-ur-Rehman et al. (2005 , 2006 , 2007 ); Bihovsky et al. (2004 ); Braun (1923 ); Fabiola et al. (1998 ); Kojić-Prodić & Rużić-Toroš (1982 ); Lombardino et al. (1971 ); Turck et al. (1996 ); Weast et al. (1984 ).

Experimental

Crystal data

C₁₃H₁₃NO₆S
M_r = 311.30
Orthorhombic, P c a 2₁
a = 11.7982 (3) Å
b = 8.7206 (2) Å
c = 13.2474 (4) Å
V = 1362.99 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 120 (2) K
0.50 × 0.30 × 0.15 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.879, T_max = 0.961
12553 measured reflections
3095 independent reflections
2849 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.100
S = 1.13
3095 reflections
194 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.64 e Å⁻³
Absolute structure: Flack (1983 ), 1466 Friedel pairs
Flack parameter: 0.00 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4	0.84	1.85	2.580 (2)	145
C3—H3A⋯O1ⁱ	0.95	2.37	3.286 (3)	163
C4—H4⋯O1ⁱⁱ	0.95	2.49	3.267 (3)	139
C11—H11A⋯O2	0.99	2.46	2.830 (3)	102
C11—H11B⋯O5	0.99	2.40	2.994 (3)	118
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y, z]$ ; (ii) $[-x, -y+2, z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CAMERON (Watkin et al., 1993 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019156/bt2729sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808019156/bt2729Isup2.hkl

checkCIF report

Comment top

Benzothiazine 1,1-dioxides are known to possess a versatile range of biological activities and have been synthesized continuously since the very first synthesis in 1923 (Braun, 1923). Among these, Piroxicam (Lombardino et al.,1971; Zia-ur-Rehman et al., 2005), and Meloxicam (Turck et al., 1996) are familiar for their analgesic and anti-inflammatory activities and are being used world wide as non-steroidal anti-inflammatory drugs (NSAIDs). Some of the 3,4-dihydro-1,2-benzothiazine-3-carboxylate 1,1-dioxide α-ketomide and P(2)—P(3) peptide mimetic aldehyde compounds act as potent calpain I inhibitors (Bihovsky et al., 2004) while 1,2-benzothiazin-3-yl-quinazolin-4(3H)-ones possess antibacterial properties (Zia-ur-Rehman et al., 2006). In continuation of our ongoing work (Zia-ur-Rehman et al., 2007; Ahmad et al., 2008), we herein report the synthesis and crystal structure of the title compound.

In this paper, the structure of the title compound (I) is reported (Scheme and figure 1). The thiazine ring, involving two double bonds, exhibits a sofa conformation; with S1/C1/C6/C7 relatively planar and N1 showing significant departure from plane due to its pyramidal geometry. The enolic hydrogen on O3 is involved in intramolecular hydrogen bonding [O3—H3···O4] with the carbonyl oxygen at C4 giving rise to a six-membered hydrogen bond ring (Table 1). The C1—S1 [1.757 (2)Å] bond is shorter than a normal C—S single bond (1.81–2.55Å) (Weast et al., 1984) due to partial double bond character and is in agreement with similar molecules (Kojić-Prodić & Ružić-Toroŝ, 1982; Fabiola et al., 1998]. Each molecule is further linked to neighbouring molecules via weaker C—H···O=S and C—H···O=C interactions (Table 1).

Related literature top

For related literature, see: Ahmad et al. (2008); Zia-ur-Rehman et al. (2005, 2006, 2007).

For related literature, see: Bihovsky et al. (2004); Braun (1923); Fabiola et al. (1998); Kojić-Prodić & Rużić-Toroš (1982); Lombardino et al. (1971); Turck et al. (1996); Weast et al. (1984).

Experimental top

A mixture of mono chloroacetone (1.94 ml; 23.5 mmoles), methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (5.0 g,19.6 mmoles), dimethyl formamide (10.0 ml) and anhydrous sodium carbonate (4.2 g,39.2 mmoles) was stirred under nitrogen atmosphere for 3.0 h at 120 ^oC.The contents were then cooled to room temperature and poured over crushed ice.Title compound (I) was precipitated as white precipitates which were washed with excess of water, filtered and dried. Yield: 4.39 g; 72%; M.p. 455 K. Crystals were grown by slow evaporation of solution of (I) in Chloroform-Methanol (1:1) mixture.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The asymmetric unit of the title compound showing the intramolecular hydrogen bond. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Perspective view of the three-dimensional crystal packing showing hydrogen-bonds and other intermolecular interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

Methyl 2-acetonyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide top

Crystal data top

C₁₃H₁₃NO₆S	F(000) = 648
M_r = 311.30	D_x = 1.517 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 6916 reflections
a = 11.7982 (3) Å	θ = 2.9–27.5°
b = 8.7206 (2) Å	µ = 0.27 mm⁻¹
c = 13.2474 (4) Å	T = 120 K
V = 1362.99 (6) Å³	Block, colourless
Z = 4	0.50 × 0.30 × 0.15 mm

Data collection top

Bruker–Nonius KappaCCD diffractometer	3095 independent reflections
Radiation source: Bruker Nonius FR591 Rotating Anode	2849 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ϕ and ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −11→11
T_min = 0.879, T_max = 0.961	l = −17→17
12553 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.0621P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.100	(Δ/σ)_max < 0.001
S = 1.13	Δρ_max = 0.57 e Å⁻³
3095 reflections	Δρ_min = −0.64 e Å⁻³
194 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.067 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1466 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (8)

Crystal data top

C₁₃H₁₃NO₆S	V = 1362.99 (6) Å³
M_r = 311.30	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 11.7982 (3) Å	µ = 0.27 mm⁻¹
b = 8.7206 (2) Å	T = 120 K
c = 13.2474 (4) Å	0.50 × 0.30 × 0.15 mm

Data collection top

Bruker–Nonius KappaCCD diffractometer	3095 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2849 reflections with I > 2σ(I)
T_min = 0.879, T_max = 0.961	R_int = 0.041
12553 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.100	Δρ_max = 0.57 e Å⁻³
S = 1.13	Δρ_min = −0.64 e Å⁻³
3095 reflections	Absolute structure: Flack (1983), 1466 Friedel pairs
194 parameters	Absolute structure parameter: 0.00 (8)
1 restraint

Special details top

Experimental. SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission: 0.6723 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command

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.

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

	x	y	z	U_iso*/U_eq
S1	0.12520 (4)	0.72682 (5)	0.71113 (5)	0.01779 (15)
O1	0.14000 (12)	0.85887 (19)	0.64793 (13)	0.0249 (4)
O2	0.21431 (12)	0.61542 (17)	0.71678 (14)	0.0255 (4)
O3	−0.19773 (12)	0.91805 (17)	0.77253 (12)	0.0204 (3)
H3	−0.2440	0.8985	0.7261	0.031*
O4	−0.27020 (12)	0.78295 (17)	0.61171 (13)	0.0229 (4)
O5	−0.15104 (13)	0.62248 (18)	0.53092 (12)	0.0234 (4)
O6	−0.03227 (14)	0.48788 (19)	0.85565 (13)	0.0287 (4)
N1	0.00988 (15)	0.63873 (19)	0.67500 (15)	0.0172 (4)
C1	0.08889 (18)	0.7943 (2)	0.83187 (17)	0.0173 (4)
C2	0.16859 (19)	0.8042 (3)	0.90839 (18)	0.0231 (5)
H2	0.2436	0.7675	0.8984	0.028*
C3	0.1371 (2)	0.8685 (3)	0.9994 (2)	0.0258 (5)
H3A	0.1909	0.8765	1.0525	0.031*
C4	0.0269 (2)	0.9218 (3)	1.01423 (18)	0.0244 (5)
H4	0.0061	0.9659	1.0771	0.029*
C5	−0.05253 (19)	0.9105 (2)	0.93717 (17)	0.0195 (4)
H5	−0.1274	0.9473	0.9476	0.023*
C6	−0.02314 (17)	0.8457 (2)	0.84476 (17)	0.0169 (4)
C7	−0.10643 (17)	0.8267 (2)	0.76334 (17)	0.0156 (4)
C8	−0.09225 (18)	0.7266 (2)	0.68505 (15)	0.0155 (4)
C9	−0.17931 (18)	0.7142 (2)	0.60656 (16)	0.0172 (4)
C10	−0.2356 (2)	0.6047 (3)	0.4522 (2)	0.0327 (6)
H10A	−0.3074	0.5716	0.4822	0.049*
H10B	−0.2098	0.5275	0.4035	0.049*
H10C	−0.2465	0.7029	0.4176	0.049*
C11	0.00404 (19)	0.4701 (2)	0.67907 (18)	0.0202 (4)
H11A	0.0763	0.4277	0.6532	0.024*
H11B	−0.0572	0.4350	0.6335	0.024*
C12	−0.01724 (18)	0.4058 (2)	0.78301 (19)	0.0216 (5)
C13	−0.0175 (2)	0.2338 (3)	0.7899 (2)	0.0329 (6)
H13A	−0.0154	0.2028	0.8609	0.049*
H13B	0.0492	0.1928	0.7549	0.049*
H13C	−0.0864	0.1935	0.7582	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0125 (2)	0.0212 (2)	0.0196 (2)	0.00081 (16)	0.0010 (2)	0.0031 (3)
O1	0.0198 (8)	0.0285 (8)	0.0263 (10)	−0.0038 (6)	0.0031 (6)	0.0092 (7)
O2	0.0170 (7)	0.0302 (8)	0.0293 (9)	0.0066 (5)	−0.0005 (7)	−0.0005 (8)
O3	0.0159 (7)	0.0222 (7)	0.0232 (8)	0.0050 (5)	−0.0035 (6)	−0.0042 (7)
O4	0.0176 (8)	0.0256 (7)	0.0256 (8)	0.0052 (6)	−0.0034 (6)	−0.0057 (7)
O5	0.0237 (9)	0.0267 (9)	0.0198 (8)	0.0058 (6)	−0.0048 (6)	−0.0056 (7)
O6	0.0361 (10)	0.0257 (8)	0.0243 (9)	0.0012 (7)	0.0043 (7)	0.0048 (7)
N1	0.0148 (9)	0.0162 (7)	0.0205 (9)	0.0014 (6)	0.0018 (7)	0.0003 (7)
C1	0.0173 (10)	0.0157 (8)	0.0190 (10)	−0.0019 (7)	0.0016 (9)	0.0019 (9)
C2	0.0164 (11)	0.0253 (10)	0.0276 (12)	−0.0014 (8)	−0.0053 (9)	0.0016 (10)
C3	0.0267 (13)	0.0267 (12)	0.0241 (12)	−0.0015 (9)	−0.0110 (9)	0.0007 (10)
C4	0.0310 (13)	0.0232 (10)	0.0191 (11)	0.0003 (9)	−0.0031 (9)	−0.0014 (9)
C5	0.0205 (11)	0.0158 (9)	0.0222 (10)	−0.0019 (7)	0.0009 (9)	0.0011 (9)
C6	0.0181 (11)	0.0119 (8)	0.0208 (11)	−0.0029 (7)	−0.0013 (8)	0.0036 (8)
C7	0.0129 (9)	0.0150 (9)	0.0188 (10)	−0.0008 (7)	0.0016 (8)	0.0030 (8)
C8	0.0137 (9)	0.0141 (9)	0.0188 (11)	−0.0009 (7)	0.0004 (8)	0.0021 (8)
C9	0.0161 (10)	0.0187 (9)	0.0168 (10)	−0.0009 (8)	0.0005 (8)	0.0004 (8)
C10	0.0323 (14)	0.0408 (12)	0.0250 (12)	0.0121 (11)	−0.0117 (10)	−0.0120 (12)
C11	0.0205 (10)	0.0168 (9)	0.0234 (11)	0.0035 (8)	−0.0005 (8)	−0.0019 (9)
C12	0.0144 (11)	0.0200 (10)	0.0303 (13)	0.0005 (7)	−0.0008 (9)	0.0035 (10)
C13	0.0332 (15)	0.0194 (11)	0.0460 (17)	0.0012 (9)	0.0037 (12)	0.0042 (11)

Geometric parameters (Å, º) top

S1—O2	1.4335 (14)	C4—C5	1.389 (3)
S1—O1	1.4345 (17)	C4—H4	0.9500
S1—N1	1.6341 (19)	C5—C6	1.392 (3)
S1—C1	1.757 (2)	C5—H5	0.9500
O3—C7	1.345 (2)	C6—C7	1.469 (3)
O3—H3	0.8400	C7—C8	1.366 (3)
O4—C9	1.231 (3)	C8—C9	1.465 (3)
O5—C9	1.325 (3)	C10—H10A	0.9800
O5—C10	1.452 (3)	C10—H10B	0.9800
O6—C12	1.212 (3)	C10—H10C	0.9800
N1—C8	1.434 (3)	C11—C12	1.508 (3)
N1—C11	1.473 (3)	C11—H11A	0.9900
C1—C2	1.385 (3)	C11—H11B	0.9900
C1—C6	1.406 (3)	C12—C13	1.503 (3)
C2—C3	1.381 (4)	C13—H13A	0.9800
C2—H2	0.9500	C13—H13B	0.9800
C3—C4	1.394 (4)	C13—H13C	0.9800
C3—H3A	0.9500

O2—S1—O1	119.03 (10)	O3—C7—C6	113.72 (18)
O2—S1—N1	107.90 (9)	C8—C7—C6	123.24 (18)
O1—S1—N1	107.93 (10)	C7—C8—N1	120.98 (18)
O2—S1—C1	110.99 (11)	C7—C8—C9	119.99 (18)
O1—S1—C1	106.99 (10)	N1—C8—C9	118.93 (18)
N1—S1—C1	102.77 (10)	O4—C9—O5	123.7 (2)
C7—O3—H3	109.5	O4—C9—C8	122.39 (19)
C9—O5—C10	115.80 (17)	O5—C9—C8	113.86 (18)
C8—N1—C11	119.38 (17)	O5—C10—H10A	109.5
C8—N1—S1	114.92 (13)	O5—C10—H10B	109.5
C11—N1—S1	119.83 (15)	H10A—C10—H10B	109.5
C2—C1—C6	121.9 (2)	O5—C10—H10C	109.5
C2—C1—S1	121.44 (17)	H10A—C10—H10C	109.5
C6—C1—S1	116.52 (16)	H10B—C10—H10C	109.5
C3—C2—C1	118.8 (2)	N1—C11—C12	114.36 (18)
C3—C2—H2	120.6	N1—C11—H11A	108.7
C1—C2—H2	120.6	C12—C11—H11A	108.7
C2—C3—C4	120.6 (2)	N1—C11—H11B	108.7
C2—C3—H3A	119.7	C12—C11—H11B	108.7
C4—C3—H3A	119.7	H11A—C11—H11B	107.6
C5—C4—C3	120.1 (2)	O6—C12—C13	122.8 (2)
C5—C4—H4	119.9	O6—C12—C11	121.97 (18)
C3—C4—H4	119.9	C13—C12—C11	115.3 (2)
C6—C5—C4	120.4 (2)	C12—C13—H13A	109.5
C6—C5—H5	119.8	C12—C13—H13B	109.5
C4—C5—H5	119.8	H13A—C13—H13B	109.5
C5—C6—C1	118.06 (19)	C12—C13—H13C	109.5
C5—C6—C7	121.68 (19)	H13A—C13—H13C	109.5
C1—C6—C7	120.2 (2)	H13B—C13—H13C	109.5
O3—C7—C8	123.04 (19)

O2—S1—N1—C8	167.94 (15)	C5—C6—C7—O3	20.3 (3)
O1—S1—N1—C8	−62.23 (17)	C1—C6—C7—O3	−161.46 (18)
C1—S1—N1—C8	50.61 (17)	C5—C6—C7—C8	−160.21 (19)
O2—S1—N1—C11	15.1 (2)	C1—C6—C7—C8	18.0 (3)
O1—S1—N1—C11	144.91 (16)	O3—C7—C8—N1	175.91 (18)
C1—S1—N1—C11	−102.25 (17)	C6—C7—C8—N1	−3.5 (3)
O2—S1—C1—C2	31.3 (2)	O3—C7—C8—C9	−0.6 (3)
O1—S1—C1—C2	−100.01 (18)	C6—C7—C8—C9	−179.97 (18)
N1—S1—C1—C2	146.46 (18)	C11—N1—C8—C7	118.1 (2)
O2—S1—C1—C6	−152.25 (15)	S1—N1—C8—C7	−34.9 (2)
O1—S1—C1—C6	76.41 (16)	C11—N1—C8—C9	−65.4 (3)
N1—S1—C1—C6	−37.13 (17)	S1—N1—C8—C9	141.61 (16)
C6—C1—C2—C3	−0.9 (3)	C10—O5—C9—O4	−0.7 (3)
S1—C1—C2—C3	175.34 (17)	C10—O5—C9—C8	179.00 (18)
C1—C2—C3—C4	0.3 (3)	C7—C8—C9—O4	−5.5 (3)
C2—C3—C4—C5	0.1 (3)	N1—C8—C9—O4	177.96 (18)
C3—C4—C5—C6	0.2 (3)	C7—C8—C9—O5	174.79 (18)
C4—C5—C6—C1	−0.7 (3)	N1—C8—C9—O5	−1.8 (3)
C4—C5—C6—C7	177.53 (19)	C8—N1—C11—C12	−73.3 (3)
C2—C1—C6—C5	1.1 (3)	S1—N1—C11—C12	78.4 (2)
S1—C1—C6—C5	−175.30 (15)	N1—C11—C12—O6	2.6 (3)
C2—C1—C6—C7	−177.19 (19)	N1—C11—C12—C13	−176.96 (19)
S1—C1—C6—C7	6.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.84	1.85	2.580 (2)	145
C3—H3A···O1ⁱ	0.95	2.37	3.286 (3)	163
C4—H4···O1ⁱⁱ	0.95	2.49	3.267 (3)	139
C11—H11A···O2	0.99	2.46	2.830 (3)	102
C11—H11B···O5	0.99	2.40	2.994 (3)	118

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃NO₆S
M_r	311.30
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	120
a, b, c (Å)	11.7982 (3), 8.7206 (2), 13.2474 (4)
V (Å³)	1362.99 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.50 × 0.30 × 0.15

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.879, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	12553, 3095, 2849
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.100, 1.13
No. of reflections	3095
No. of parameters	194
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.64
Absolute structure	Flack (1983), 1466 Friedel pairs
Absolute structure parameter	0.00 (8)

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CAMERON (Watkin et al., 1993), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.8400	1.8500	2.580 (2)	145.00
C3—H3A···O1ⁱ	0.9500	2.3700	3.286 (3)	163.00
C4—H4···O1ⁱⁱ	0.9500	2.4900	3.267 (3)	139.00
C11—H11A···O2	0.9900	2.4600	2.830 (3)	102.00
C11—H11B···O5	0.9900	2.4000	2.994 (3)	118.00

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

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for the provision of a research grant for the project.

References

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