(2R)-2-(1,3-Dioxoisoindolin-2-yl)-4-(methyl­sulfan­yl)butanoic acid

Raza, A.R.; Tahir, M.N.; Saddiqa, A.; Danish, M.; Iqbal, M.S.

doi:10.1107/S1600536809028992

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o2002

doi:10.1107/S1600536809028992

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(2R)-2-(1,3-Dioxoisoindolin-2-yl)-4-(methylsulfanyl)butanoic acid

Abdul Rauf Raza,^a M. Nawaz Tahir,^b ^* Aisha Saddiqa,^a Muhammad Danish ^a and M. Saeed Iqbal ^c

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

(Received 8 July 2009; accepted 22 July 2009; online 25 July 2009)

The title compound, C₁₃H₁₃NO₄S, the 1,3-dioxoisoindolin-2-yl unit is planar (r.m.s. deviation 0.0192 Å) and is oriented at a dihedral angle of 79.14 (18)° to the carboxylate group. An intramolecular C—H⋯O hydrogen bond leads to the formation of a planar (r.m.s. deviation 0.0419 Å)R(5) ring motif. In the crystal, molecules are connected through O—H⋯O and C—H⋯O hydrogen bonds with R₂²(9) ring motifs into chains extending along the b axis.

Related literature

For the biological activity of isocoumarin and 3,4-dihydroisocoumarin, see: Hill (1986 ); Canedo et al. (1997 ); Whyte et al. (1996 ). For related structures, see: Barooah et al. (2007 ); Feeder & Jones (1994 ); Rajagopal et al. (2003 ). For graph-set motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₃H₁₃NO₄S
M_r = 279.30
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.7923 (6) Å
b = 9.9581 (8) Å
c = 20.0970 (17) Å
V = 1359.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.20 × 0.14 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.969, T_max = 0.985
7865 measured reflections
1864 independent reflections
1679 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.098
S = 1.06
1864 reflections
179 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3ⁱ	0.77 (3)	1.96 (3)	2.673 (3)	154 (3)
C3—H3⋯O2ⁱⁱ	0.9300	2.4200	3.328 (4)	165.00
C9—H9⋯O4	0.96 (3)	2.48 (3)	2.905 (3)	106.4 (18)
C11—H11B⋯O1ⁱⁱⁱ	0.9700	2.5400	3.443 (3)	156.00
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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: 10.1107/S1600536809028992/pb2001sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028992/pb2001Isup2.hkl

checkCIF report

Comment top

Isocoumarin and 3,4-dihydroisocoumarin have shown an impressive array of biological activities such as anti-tumor (Hill et al., 1986), anti-leucemic (Canedo et al., 1997) and anti-microbial (Whyte et al., 1996). The titled compound (I, Fig. 1) is an intermediate towards the synthesis of chiral isocoumarin. The biological activity of the title compound and synthesis of its complexes are in progress.

The crystal structures of 2-Phthalimidoethanoic acid monohydrate (Feeder & Jones, 1994), N-Phthaloylglycine (Barooah et al., 2007) and DL-Methioninium trichloroacetate (Rajagopal et al., 2003) have been published which contain the moieties of the title compound.

In the title compound the aromatic ring and heterocyclic ring along with O-atoms of carbonyl groups A (C1—C8/N1/O3/O4), the linear chain B (C9—C11/S1/C12) and the carboxylate group C (O1/C13/O2) are planar. There exists an intramolecular H-bond of type C—H···O completing a planar S(5) ring motif (Bernstein et al., 1995). The value of dihedral angle between A/B, A/C and B/C is 80.04 (7)°, 79.14 (18)° and 20.54 (30)°, respectively. Due to the intermolecular H-bonding (Table 1), the molecules are connected in one dimensional polymeric chains through ring motifs R₂²(9) extending along the b-axis.

Related literature top

For the biological activity of isocoumarin and 3,4-dihydroisocoumarin, see: Hill (1986); Canedo et al. (1997); Whyte et al. (1996). For related structures, see: Barooah et al. (2007); Feeder & Jones (1994); Rajagopal et al. (2003). For graph-set motifs, see: Bernstein et al. (1995).

Experimental top

The methionine (2.0 g, 13.4 mmol) and phthalic anhydride (2.13 g, 14.38 mmol) were added to a flask with constant stirring at 423 K for 2 h. The reaction mixture was brought to room temperature and the crystalline phthallic anhydride on the walls of the flask were removed. The solid crude product was purified by crystallization from ethanol/water (7:3) that afforded colorless prisms of the title compound (I).

Yield 81%.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 50% probability level. H-atoms are shown by small circles of arbitrary radii. The dotted line indicate the intramolecular H-bond.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form polymeric chains extending along the b-axis.

(2R)-2-(1,3-Dioxoisoindolin-2-yl)-4-(methylsulfanyl)butanoic acid top

Crystal data top

C₁₃H₁₃NO₄S	F(000) = 584
M_r = 279.30	D_x = 1.365 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1864 reflections
a = 6.7923 (6) Å	θ = 2.3–28.0°
b = 9.9581 (8) Å	µ = 0.25 mm⁻¹
c = 20.0970 (17) Å	T = 296 K
V = 1359.3 (2) Å³	Prismatic, colorless
Z = 4	0.20 × 0.14 × 0.10 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	1864 independent reflections
Radiation source: fine-focus sealed tube	1679 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 7.50 pixels mm^-1	θ_max = 28.0°, θ_min = 2.3°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→7
T_min = 0.969, T_max = 0.985	l = −23→26
7865 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.057P)² + 0.2154P] where P = (F_o² + 2F_c²)/3
1864 reflections	(Δ/σ)_max < 0.001
179 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₃H₁₃NO₄S	V = 1359.3 (2) Å³
M_r = 279.30	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.7923 (6) Å	µ = 0.25 mm⁻¹
b = 9.9581 (8) Å	T = 296 K
c = 20.0970 (17) Å	0.20 × 0.14 × 0.10 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	1864 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1679 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.985	R_int = 0.024
7865 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.20 e Å⁻³
1864 reflections	Δρ_min = −0.33 e Å⁻³
179 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 esds 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	−0.16661 (11)	0.67441 (7)	0.42200 (3)	0.0592 (2)
O1	0.3364 (3)	0.2322 (2)	0.26744 (9)	0.0561 (6)
O2	0.3978 (3)	0.3163 (2)	0.36803 (8)	0.0651 (7)
O3	0.3730 (2)	0.55141 (18)	0.23747 (8)	0.0475 (5)
O4	−0.2132 (3)	0.3346 (2)	0.21563 (10)	0.0656 (7)
N1	0.0832 (3)	0.43417 (17)	0.24261 (8)	0.0355 (5)
C1	0.2192 (3)	0.5168 (2)	0.21199 (11)	0.0361 (6)
C2	0.1381 (4)	0.5487 (2)	0.14518 (10)	0.0390 (6)
C3	0.2158 (5)	0.6255 (3)	0.09427 (12)	0.0543 (8)
C4	0.1055 (5)	0.6347 (3)	0.03591 (13)	0.0638 (9)
C5	−0.0735 (6)	0.5715 (3)	0.03025 (14)	0.0668 (9)
C6	−0.1514 (5)	0.4944 (3)	0.08144 (13)	0.0594 (8)
C7	−0.0415 (4)	0.4844 (2)	0.13909 (11)	0.0430 (6)
C8	−0.0790 (3)	0.4072 (2)	0.20120 (11)	0.0422 (7)
C9	0.1029 (3)	0.3829 (2)	0.31004 (10)	0.0358 (6)
C10	0.0710 (3)	0.4911 (2)	0.36262 (11)	0.0423 (6)
C11	−0.1370 (4)	0.5462 (3)	0.36027 (11)	0.0465 (7)
C12	−0.4193 (6)	0.7176 (4)	0.40992 (18)	0.0927 (14)
C13	0.2982 (3)	0.3089 (2)	0.31883 (11)	0.0412 (6)
H1	0.435 (5)	0.196 (3)	0.2742 (16)	0.0673*
H3	0.33622	0.66910	0.09873	0.0652*
H4	0.15390	0.68438	0.00030	0.0764*
H5	−0.14459	0.58059	−0.00904	0.0801*
H6	−0.27220	0.45141	0.07712	0.0713*
H9	0.002 (4)	0.316 (3)	0.3151 (12)	0.0430*
H10A	0.09595	0.45360	0.40636	0.0507*
H10B	0.16374	0.56373	0.35543	0.0507*
H11A	−0.23038	0.47436	0.36834	0.0558*
H11B	−0.16321	0.58325	0.31651	0.0558*
H12A	−0.43704	0.75226	0.36576	0.1385*
H12B	−0.45705	0.78452	0.44181	0.1385*
H12C	−0.49950	0.63905	0.41568	0.1385*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0668 (4)	0.0560 (3)	0.0549 (4)	0.0046 (3)	0.0121 (3)	−0.0137 (3)
O1	0.0542 (10)	0.0646 (11)	0.0494 (10)	0.0238 (9)	−0.0114 (9)	−0.0182 (9)
O2	0.0685 (11)	0.0852 (14)	0.0417 (9)	0.0298 (11)	−0.0157 (8)	−0.0100 (9)
O3	0.0448 (8)	0.0545 (9)	0.0432 (9)	−0.0130 (8)	−0.0076 (7)	0.0070 (7)
O4	0.0510 (10)	0.0801 (13)	0.0656 (12)	−0.0252 (10)	−0.0100 (9)	0.0065 (11)
N1	0.0360 (8)	0.0381 (8)	0.0323 (8)	−0.0015 (8)	−0.0004 (7)	0.0012 (7)
C1	0.0399 (10)	0.0326 (9)	0.0359 (10)	0.0005 (8)	0.0000 (8)	−0.0018 (8)
C2	0.0508 (12)	0.0346 (9)	0.0315 (10)	0.0027 (9)	−0.0023 (9)	−0.0029 (8)
C3	0.0728 (17)	0.0508 (12)	0.0394 (12)	−0.0090 (12)	−0.0011 (12)	0.0059 (10)
C4	0.097 (2)	0.0591 (14)	0.0353 (12)	−0.0061 (16)	−0.0088 (14)	0.0057 (11)
C5	0.100 (2)	0.0601 (15)	0.0404 (13)	0.0027 (17)	−0.0261 (15)	0.0002 (12)
C6	0.0686 (16)	0.0573 (13)	0.0524 (14)	−0.0024 (14)	−0.0235 (14)	−0.0051 (12)
C7	0.0502 (12)	0.0398 (10)	0.0391 (11)	0.0021 (10)	−0.0066 (10)	−0.0046 (9)
C8	0.0398 (11)	0.0440 (11)	0.0427 (12)	−0.0016 (9)	−0.0058 (9)	−0.0035 (9)
C9	0.0382 (10)	0.0369 (10)	0.0324 (10)	0.0002 (9)	0.0022 (8)	0.0020 (8)
C10	0.0460 (12)	0.0467 (11)	0.0342 (10)	0.0049 (10)	0.0008 (9)	−0.0039 (9)
C11	0.0494 (12)	0.0517 (12)	0.0383 (11)	0.0096 (11)	0.0036 (10)	−0.0045 (10)
C12	0.089 (2)	0.111 (3)	0.078 (2)	0.053 (2)	0.0201 (19)	−0.001 (2)
C13	0.0466 (11)	0.0424 (10)	0.0347 (10)	0.0074 (10)	0.0002 (9)	0.0013 (9)

Geometric parameters (Å, º) top

S1—C11	1.792 (3)	C7—C8	1.488 (3)
S1—C12	1.786 (4)	C9—C13	1.528 (3)
O1—C13	1.311 (3)	C9—C10	1.525 (3)
O2—C13	1.200 (3)	C10—C11	1.516 (3)
O3—C1	1.213 (3)	C3—H3	0.9300
O4—C8	1.199 (3)	C4—H4	0.9300
O1—H1	0.77 (3)	C5—H5	0.9300
N1—C8	1.407 (3)	C6—H6	0.9300
N1—C9	1.454 (3)	C9—H9	0.96 (3)
N1—C1	1.382 (3)	C10—H10A	0.9700
C1—C2	1.486 (3)	C10—H10B	0.9700
C2—C7	1.383 (4)	C11—H11A	0.9700
C2—C3	1.382 (3)	C11—H11B	0.9700
C3—C4	1.395 (4)	C12—H12A	0.9600
C4—C5	1.374 (5)	C12—H12B	0.9600
C5—C6	1.389 (4)	C12—H12C	0.9600
C6—C7	1.382 (4)

S1···C7ⁱ	3.610 (2)	C10···O3	3.301 (3)
S1···H5ⁱⁱ	3.1600	C11···C8	3.506 (3)
S1···H12Bⁱⁱⁱ	3.1100	C13···O3	2.960 (3)
O1···N1	2.693 (3)	C1···H1^vi	2.96 (3)
O1···C1	3.148 (3)	C1···H10B	2.9400
O1···O3^iv	2.673 (3)	C2···H9ⁱ	2.94 (3)
O2···C4^v	3.409 (3)	C3···H9ⁱ	3.02 (3)
O2···C3^iv	3.328 (4)	C8···H11B	2.9600
O3···C13	2.960 (3)	H1···O3^iv	1.96 (3)
O3···C10	3.301 (3)	H1···C1^iv	2.96 (3)
O3···O4ⁱ	3.165 (3)	H3···O2^vi	2.4200
O3···O1^vi	2.673 (3)	H4···O2^viii	2.6800
O4···O3^vii	3.165 (3)	H5···S1^ix	3.1600
O1···H12A^vii	2.7700	H6···H12B^x	2.5100
O1···H11B^vii	2.5400	H9···O4	2.48 (3)
O2···H3^iv	2.4200	H9···H11A	2.4700
O2···H10A	2.5800	H9···C2^vii	2.94 (3)
O2···H4^v	2.6800	H9···C3^vii	3.02 (3)
O3···H10B	2.7700	H10A···O2	2.5800
O3···H1^vi	1.96 (3)	H10B···O3	2.7700
O4···H9	2.48 (3)	H10B···C1	2.9400
N1···O1	2.693 (3)	H11A···H9	2.4700
N1···H11B	2.6900	H11B···N1	2.6900
C1···O1	3.148 (3)	H11B···C8	2.9600
C3···O2^vi	3.328 (4)	H11B···O1ⁱ	2.5400
C4···O2^viii	3.409 (3)	H12A···O1ⁱ	2.7700
C7···S1^vii	3.610 (2)	H12B···S1^xi	3.1100
C8···C11	3.506 (3)	H12B···H6^xii	2.5100

C11—S1—C12	100.68 (15)	O1—C13—O2	125.0 (2)
C13—O1—H1	108 (2)	C2—C3—H3	122.00
C1—N1—C8	111.95 (17)	C4—C3—H3	122.00
C1—N1—C9	124.23 (18)	C3—C4—H4	119.00
C8—N1—C9	123.80 (18)	C5—C4—H4	120.00
O3—C1—N1	123.8 (2)	C4—C5—H5	119.00
O3—C1—C2	129.8 (2)	C6—C5—H5	119.00
N1—C1—C2	106.38 (18)	C5—C6—H6	121.00
C1—C2—C7	107.94 (18)	C7—C6—H6	121.00
C3—C2—C7	121.8 (2)	N1—C9—H9	106.0 (15)
C1—C2—C3	130.2 (2)	C10—C9—H9	108.4 (16)
C2—C3—C4	117.0 (3)	C13—C9—H9	105.8 (17)
C3—C4—C5	121.0 (3)	C9—C10—H10A	109.00
C4—C5—C6	122.0 (3)	C9—C10—H10B	109.00
C5—C6—C7	117.1 (3)	C11—C10—H10A	109.00
C2—C7—C8	108.42 (19)	C11—C10—H10B	109.00
C6—C7—C8	130.4 (2)	H10A—C10—H10B	108.00
C2—C7—C6	121.2 (2)	S1—C11—H11A	110.00
O4—C8—N1	124.6 (2)	S1—C11—H11B	110.00
N1—C8—C7	105.28 (18)	C10—C11—H11A	110.00
O4—C8—C7	130.1 (2)	C10—C11—H11B	110.00
N1—C9—C10	112.62 (16)	H11A—C11—H11B	108.00
C10—C9—C13	112.59 (17)	S1—C12—H12A	109.00
N1—C9—C13	110.92 (17)	S1—C12—H12B	109.00
C9—C10—C11	111.50 (18)	S1—C12—H12C	109.00
S1—C11—C10	109.93 (17)	H12A—C12—H12B	110.00
O1—C13—C9	111.22 (18)	H12A—C12—H12C	109.00
O2—C13—C9	123.7 (2)	H12B—C12—H12C	109.00

C12—S1—C11—C10	−178.69 (19)	C1—C2—C7—C8	−1.1 (2)
C8—N1—C1—O3	−178.4 (2)	C3—C2—C7—C6	0.0 (4)
C8—N1—C1—C2	1.0 (2)	C3—C2—C7—C8	178.1 (2)
C9—N1—C1—O3	2.7 (3)	C2—C3—C4—C5	1.0 (4)
C9—N1—C1—C2	−177.97 (18)	C3—C4—C5—C6	−1.0 (5)
C1—N1—C8—O4	177.4 (2)	C4—C5—C6—C7	0.5 (5)
C1—N1—C8—C7	−1.6 (2)	C5—C6—C7—C2	0.0 (4)
C9—N1—C8—O4	−3.6 (3)	C5—C6—C7—C8	−177.6 (3)
C9—N1—C8—C7	177.32 (18)	C2—C7—C8—O4	−177.3 (2)
C1—N1—C9—C10	72.2 (2)	C2—C7—C8—N1	1.7 (2)
C1—N1—C9—C13	−55.0 (2)	C6—C7—C8—O4	0.6 (4)
C8—N1—C9—C10	−106.6 (2)	C6—C7—C8—N1	179.6 (3)
C8—N1—C9—C13	126.1 (2)	N1—C9—C10—C11	63.5 (2)
O3—C1—C2—C3	0.3 (4)	C13—C9—C10—C11	−170.15 (18)
O3—C1—C2—C7	179.4 (2)	N1—C9—C13—O1	−42.6 (2)
N1—C1—C2—C3	−179.0 (2)	N1—C9—C13—O2	140.5 (2)
N1—C1—C2—C7	0.2 (2)	C10—C9—C13—O1	−169.85 (18)
C1—C2—C3—C4	178.6 (2)	C10—C9—C13—O2	13.3 (3)
C7—C2—C3—C4	−0.5 (4)	C9—C10—C11—S1	−179.19 (15)
C1—C2—C7—C6	−179.3 (2)

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x−1/2, −y+1, z+1/2; (iii) x+1/2, −y+3/2, −z+1; (iv) −x+1, y−1/2, −z+1/2; (v) −x+1/2, −y+1, z+1/2; (vi) −x+1, y+1/2, −z+1/2; (vii) −x, y−1/2, −z+1/2; (viii) −x+1/2, −y+1, z−1/2; (ix) −x−1/2, −y+1, z−1/2; (x) −x−1, y−1/2, −z+1/2; (xi) x−1/2, −y+3/2, −z+1; (xii) −x−1, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^iv	0.77 (3)	1.96 (3)	2.673 (3)	154 (3)
C3—H3···O2^vi	0.9300	2.4200	3.328 (4)	165.00
C9—H9···O4	0.96 (3)	2.48 (3)	2.905 (3)	106.4 (18)
C11—H11B···O1ⁱ	0.9700	2.5400	3.443 (3)	156.00

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃NO₄S
M_r	279.30
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	6.7923 (6), 9.9581 (8), 20.0970 (17)
V (Å³)	1359.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.20 × 0.14 × 0.10

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.969, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	7865, 1864, 1679
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.098, 1.06
No. of reflections	1864
No. of parameters	179
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.33

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), 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
O1—H1···O3ⁱ	0.77 (3)	1.96 (3)	2.673 (3)	154 (3)
C3—H3···O2ⁱⁱ	0.9300	2.4200	3.328 (4)	165.00
C9—H9···O4	0.96 (3)	2.48 (3)	2.905 (3)	106.4 (18)
C11—H11B···O1ⁱⁱⁱ	0.9700	2.5400	3.443 (3)	156.00

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

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, and Bana International, Karachi, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore, and for technical support, respectively.

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