Methyl 2-[(methyl­sulfon­yl)(prop­yl)amino]benzoate

Shafiq, M.; Tahir, M.N.; Khan, I.U.; Arshad, M.N.; Haider, Z.

doi:10.1107/S1600536809054920

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o248

doi:10.1107/S1600536809054920

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Methyl 2-[(methylsulfonyl)(propyl)amino]benzoate

Muhammad Shafiq,^a M. Nawaz Tahir,^b ^* Islam Ullah Khan,^a Muhammad Nadeem Arshad ^a and Zeeshan Haider ^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 19 December 2009; accepted 21 December 2009; online 24 December 2009)

The asymmetric unit of the title compound, C₁₂H₁₇NO₄S, contains two molecules, both of which show disorder of the two terminal C atoms of the propyl chain over two sets of sites with an occupancy ratio of 0.581 (6):0.419 (6). Intramolecular C—H⋯O interactions help to establish the molecular conformations: in one molecule, the dihedral angle between the methyl ester group and the benzene ring is 41.0 (2)°, whereas in the other molecule it is 36.12 (17)°. In the crystal, molecules are linked by intermolecular C—H⋯O and C—H⋯π interactions.

Related literature

For related structures, see: Shafiq et al. (2008 , 2009a ,b ).

Experimental

Crystal data

C₁₂H₁₇NO₄S
M_r = 271.33
Monoclinic, P 2₁ /c
a = 10.1762 (4) Å
b = 15.0178 (6) Å
c = 18.0900 (8) Å
β = 92.787 (2)°
V = 2761.3 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.25 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.955, T_max = 0.968
25991 measured reflections
5409 independent reflections
2607 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.193
S = 1.01
5409 reflections
328 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C14–C19 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O8ⁱ	0.93	2.59	3.483 (6)	161
C11A—H11C⋯O1	0.96	2.57	3.486 (15)	159
C16—H16⋯O4	0.93	2.51	3.429 (5)	168
C20—H20C⋯O3ⁱⁱ	0.96	2.57	3.172 (6)	121
C21—H21A⋯O1	0.97	2.55	3.192 (6)	124
C12—H12A⋯Cg2ⁱⁱⁱ	0.96	2.84	3.660 (5)	144
C18—H18⋯Cg1^iv	0.93	2.87	3.588 (5)	135
Symmetry codes: (i) x+1, y, z; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 (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/S1600536809054920/hb5288sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809054920/hb5288Isup2.hkl

checkCIF report

Comment top

In continuation to our work on the synthesis of benzothiazine derivatives, we have reported various molecules of this series (Shafiq et al., 2008, 2009a, 2009b). The title compound (I, Fig. 1, Fig. 2) is being reported here in this context.

The asymmtric unit of title compound consists of two molecules. In both molecules the two terminal C-atoms of propyl moiety are disordered over two set of sites with occupancy ratio of 0.581 (6):0.419 (6). The two molecules of asymmetric units differ from each other as the dihedral angle between methyl ester A (O2/C1/O1/C8) with benzene ring B (C2–C7) is 40.96 (21)°, whereas in the other molecule it is 36.12 (17)° between C (O6/C13/O5/C20) and D (C13–C19). The molecules are stabilized due to intra as well as intermolecular and C–H···π interactions (Table 1, Fig. 2).

Related literature top

For related structures, see: Shafiq et al. (2008, 2009a,b).

Experimental top

For the preparation of the title compound, the suspension of hexane-washed sodium hydride (50% in mineral oil) was prepared in dry dimethylformamide (3 ml). A solution of methyl N-methylsulfonylanthranilate (70 mg, 0.306 mmol) in dry dimethylformamide (5 ml) was added to the suspension and stirred for 45 min at room temperature. Then, a solution of propyl iodide (156.40 mg, 0.92 mmol) was added to it. The resulting white suspension was stirred for 2.5–3 h, added to ice and pH adjusted at 4–4.5 and kept in freezer. Solid product obtained was filtered and dried to obtain white prisms of title compound.

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 (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 (I) with the atom numbering scheme having atoms of greater occupancy ratio. The thermal ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 2. View of (I) with the atom numbering scheme having atoms of smaller occupancy ratio. The thermal ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 3. The partial packing of (I), which shows that the molecules are stacked in polymeric chains due to intermolecular H-bodings that extend along the crystallographic b axis.

Methyl 2-[(methylsulfonyl)(propyl)amino]benzoate top

Crystal data top

C₁₂H₁₇NO₄S	F(000) = 1152
M_r = 271.33	D_x = 1.305 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2607 reflections
a = 10.1762 (4) Å	θ = 2.0–26.0°
b = 15.0178 (6) Å	µ = 0.24 mm⁻¹
c = 18.0900 (8) Å	T = 296 K
β = 92.787 (2)°	Prismatic, white
V = 2761.3 (2) Å³	0.25 × 0.12 × 0.10 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	5409 independent reflections
Radiation source: fine-focus sealed tube	2607 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
Detector resolution: 7.70 pixels mm^-1	θ_max = 26.0°, θ_min = 2.0°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −18→18
T_min = 0.955, T_max = 0.968	l = −22→22
25991 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.193	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0837P)² + 1.0657P] where P = (F_o² + 2F_c²)/3
5409 reflections	(Δ/σ)_max < 0.001
328 parameters	Δρ_max = 0.50 e Å⁻³
7 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₂H₁₇NO₄S	V = 2761.3 (2) Å³
M_r = 271.33	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.1762 (4) Å	µ = 0.24 mm⁻¹
b = 15.0178 (6) Å	T = 296 K
c = 18.0900 (8) Å	0.25 × 0.12 × 0.10 mm
β = 92.787 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5409 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2607 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.968	R_int = 0.078
25991 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	7 restraints
wR(F²) = 0.193	H-atom parameters constrained
S = 1.01	Δρ_max = 0.50 e Å⁻³
5409 reflections	Δρ_min = −0.40 e Å⁻³
328 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	Occ. (<1)
S1	0.56276 (10)	0.24818 (8)	0.18894 (6)	0.0513 (4)
O1	0.3570 (3)	0.1598 (3)	0.0442 (2)	0.0822 (15)
O2	0.3266 (3)	0.2903 (2)	−0.01117 (18)	0.0740 (13)
O3	0.4772 (3)	0.3112 (2)	0.15293 (16)	0.0706 (13)
O4	0.5151 (3)	0.1951 (2)	0.24718 (17)	0.0744 (13)
N1	0.6139 (3)	0.1809 (2)	0.12571 (18)	0.0499 (11)
C1	0.4009 (4)	0.2243 (3)	0.0166 (2)	0.0544 (19)
C2	0.5427 (4)	0.2403 (3)	0.0037 (2)	0.0444 (14)
C3	0.5756 (4)	0.2752 (3)	−0.0643 (2)	0.0527 (16)
C4	0.7044 (5)	0.2844 (3)	−0.0819 (3)	0.0598 (17)
C5	0.8031 (4)	0.2615 (3)	−0.0303 (3)	0.0632 (19)
C6	0.7722 (4)	0.2291 (3)	0.0375 (3)	0.0557 (16)
C7	0.6419 (4)	0.2167 (3)	0.0549 (2)	0.0450 (14)
C8	0.1861 (4)	0.2808 (4)	−0.0041 (3)	0.097 (3)
C9	0.6872 (5)	0.0997 (3)	0.1507 (3)	0.079 (2)
C10A	0.6733 (13)	0.0159 (9)	0.1078 (9)	0.132 (3)	0.581 (6)
C11A	0.5345 (13)	−0.0144 (10)	0.1283 (8)	0.132 (3)	0.581 (6)
C12	0.6994 (4)	0.3062 (3)	0.2254 (3)	0.0604 (17)
C11B	0.616 (2)	−0.0690 (11)	0.1372 (10)	0.132 (3)	0.419 (6)
C10B	0.6124 (19)	0.0243 (11)	0.1107 (12)	0.132 (3)	0.419 (6)
S2	0.06182 (10)	0.20113 (8)	0.25426 (7)	0.0580 (4)
O5	−0.1063 (3)	−0.0120 (3)	0.2656 (2)	0.0812 (14)
O6	−0.1371 (3)	−0.0088 (2)	0.38509 (17)	0.0717 (13)
O7	−0.0179 (3)	0.1979 (2)	0.31664 (18)	0.0755 (11)
O8	0.0053 (3)	0.2294 (3)	0.1850 (2)	0.0885 (14)
N2	0.1202 (3)	0.1019 (2)	0.24272 (18)	0.0494 (12)
C13	−0.0629 (4)	−0.0033 (3)	0.3280 (3)	0.0556 (17)
C14	0.0786 (4)	0.0076 (3)	0.3503 (2)	0.0449 (16)
C15	0.1667 (4)	0.0543 (3)	0.3081 (2)	0.0448 (16)
C16	0.2983 (4)	0.0561 (3)	0.3294 (3)	0.0548 (17)
C17	0.3441 (4)	0.0123 (3)	0.3916 (3)	0.0661 (19)
C18	0.2600 (5)	−0.0339 (3)	0.4335 (3)	0.0649 (17)
C19	0.1271 (4)	−0.0351 (3)	0.4137 (3)	0.0569 (17)
C20	−0.2745 (4)	−0.0294 (4)	0.3686 (3)	0.089 (2)
C21	0.1850 (5)	0.0829 (4)	0.1726 (3)	0.082 (2)
C22A	0.1036 (14)	0.0153 (10)	0.1341 (8)	0.132 (3)	0.581 (6)
C23A	0.1593 (14)	−0.0270 (9)	0.0668 (7)	0.132 (3)	0.581 (6)
C24	0.1951 (5)	0.2699 (3)	0.2772 (3)	0.0776 (19)
C23B	0.0401 (17)	−0.0269 (13)	0.1068 (10)	0.132 (3)	0.419 (6)
C22B	0.1746 (18)	−0.0121 (14)	0.1428 (12)	0.132 (3)	0.419 (6)
H4	0.72516	0.30591	−0.12807	0.0720*
H3	0.50905	0.29256	−0.09837	0.0634*
H8A	0.15863	0.22292	−0.02137	0.1453*
H8B	0.14059	0.32570	−0.03309	0.1453*
H8C	0.16584	0.28730	0.04692	0.1453*
H9A	0.77999	0.11479	0.15369	0.0946*
H9B	0.66248	0.08683	0.20068	0.0946*
H10A	0.73989	−0.02731	0.12339	0.1582*	0.581 (6)
H10B	0.67740	0.02645	0.05509	0.1582*	0.581 (6)
H11A	0.53481	−0.02692	0.18035	0.1977*	0.581 (6)
H11B	0.51025	−0.06709	0.10089	0.1977*	0.581 (6)
H11C	0.47223	0.03209	0.11640	0.1977*	0.581 (6)
H12A	0.74009	0.33773	0.18643	0.0906*
H12B	0.76128	0.26493	0.24797	0.0906*
H12C	0.67209	0.34778	0.26191	0.0906*
H5	0.89078	0.26802	−0.04155	0.0756*
H6	0.83923	0.21524	0.07235	0.0665*
H10C	0.52060	0.04192	0.10716	0.1582*	0.419 (6)
H10D	0.64197	0.02323	0.06052	0.1582*	0.419 (6)
H11D	0.61294	−0.10870	0.09558	0.1977*	0.419 (6)
H11E	0.54081	−0.07986	0.16638	0.1977*	0.419 (6)
H11F	0.69491	−0.07898	0.16696	0.1977*	0.419 (6)
H17	0.43332	0.01407	0.40544	0.0795*
H16	0.35661	0.08746	0.30122	0.0657*
H20A	−0.31611	0.01976	0.34291	0.1338*
H20B	−0.31734	−0.03998	0.41394	0.1338*
H20C	−0.28119	−0.08168	0.33812	0.1338*
H21A	0.18963	0.13638	0.14277	0.0977*
H21B	0.27359	0.06069	0.18276	0.0977*
H22A	0.01994	0.04238	0.11918	0.1582*	0.581 (6)
H22B	0.08591	−0.03154	0.16917	0.1582*	0.581 (6)
H23A	0.14796	0.01266	0.02539	0.1977*	0.581 (6)
H23B	0.11414	−0.08189	0.05589	0.1977*	0.581 (6)
H23C	0.25133	−0.03867	0.07639	0.1977*	0.581 (6)
H24A	0.25346	0.27095	0.23705	0.1170*
H24B	0.24125	0.24753	0.32089	0.1170*
H24C	0.16432	0.32910	0.28629	0.1170*
H18	0.29179	−0.06454	0.47530	0.0778*
H19	0.06943	−0.06503	0.44334	0.0684*
H22C	0.24098	−0.02177	0.10690	0.1582*	0.419 (6)
H22D	0.18982	−0.05415	0.18295	0.1582*	0.419 (6)
H23D	−0.02474	−0.02240	0.14340	0.1977*	0.419 (6)
H23E	0.03615	−0.08499	0.08474	0.1977*	0.419 (6)
H23F	0.02312	0.01742	0.06925	0.1977*	0.419 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0426 (6)	0.0712 (8)	0.0403 (6)	0.0018 (5)	0.0048 (4)	0.0047 (6)
O1	0.0583 (19)	0.100 (3)	0.088 (3)	−0.0200 (19)	0.0010 (18)	0.031 (2)
O2	0.0456 (17)	0.096 (3)	0.080 (2)	0.0064 (17)	−0.0020 (16)	0.028 (2)
O3	0.0594 (18)	0.098 (3)	0.054 (2)	0.0344 (17)	−0.0012 (15)	−0.0018 (18)
O4	0.0695 (19)	0.106 (3)	0.0490 (19)	−0.0232 (18)	0.0167 (16)	0.0120 (19)
N1	0.0535 (19)	0.056 (2)	0.040 (2)	0.0046 (17)	−0.0007 (16)	0.0079 (17)
C1	0.049 (3)	0.072 (4)	0.042 (3)	−0.005 (2)	0.000 (2)	0.008 (2)
C2	0.048 (2)	0.048 (3)	0.037 (2)	−0.0028 (19)	0.0003 (19)	0.001 (2)
C3	0.061 (3)	0.059 (3)	0.038 (2)	−0.007 (2)	0.001 (2)	0.001 (2)
C4	0.074 (3)	0.064 (3)	0.043 (3)	−0.015 (2)	0.018 (2)	−0.005 (2)
C5	0.051 (3)	0.083 (4)	0.057 (3)	−0.007 (2)	0.018 (2)	−0.008 (3)
C6	0.051 (2)	0.067 (3)	0.049 (3)	0.004 (2)	0.003 (2)	−0.003 (2)
C7	0.048 (2)	0.050 (3)	0.037 (2)	−0.0003 (19)	0.0030 (19)	−0.0008 (19)
C8	0.049 (3)	0.143 (6)	0.099 (5)	0.006 (3)	0.001 (3)	0.022 (4)
C9	0.106 (4)	0.059 (4)	0.072 (4)	0.008 (3)	0.005 (3)	0.012 (3)
C10A	0.156 (6)	0.125 (5)	0.116 (4)	0.008 (4)	0.018 (4)	−0.031 (4)
C11A	0.156 (6)	0.125 (5)	0.116 (4)	0.008 (4)	0.018 (4)	−0.031 (4)
C12	0.063 (3)	0.064 (3)	0.054 (3)	−0.006 (2)	0.000 (2)	0.000 (2)
C11B	0.156 (6)	0.125 (5)	0.116 (4)	0.008 (4)	0.018 (4)	−0.031 (4)
C10B	0.156 (6)	0.125 (5)	0.116 (4)	0.008 (4)	0.018 (4)	−0.031 (4)
S2	0.0460 (6)	0.0661 (8)	0.0621 (8)	0.0074 (5)	0.0061 (5)	0.0158 (6)
O5	0.065 (2)	0.116 (3)	0.062 (2)	−0.028 (2)	−0.0037 (18)	0.012 (2)
O6	0.0513 (18)	0.103 (3)	0.062 (2)	−0.0208 (17)	0.0156 (16)	−0.0030 (19)
O7	0.0662 (19)	0.086 (2)	0.077 (2)	0.0189 (17)	0.0312 (18)	0.0109 (19)
O8	0.076 (2)	0.114 (3)	0.074 (2)	0.023 (2)	−0.0118 (19)	0.035 (2)
N2	0.051 (2)	0.057 (2)	0.041 (2)	0.0002 (17)	0.0104 (16)	0.0067 (17)
C13	0.055 (3)	0.060 (3)	0.052 (3)	−0.016 (2)	0.004 (3)	0.004 (2)
C14	0.048 (2)	0.044 (3)	0.043 (3)	−0.0025 (19)	0.004 (2)	0.002 (2)
C15	0.047 (2)	0.044 (3)	0.044 (3)	0.0004 (19)	0.0072 (19)	−0.001 (2)
C16	0.048 (3)	0.049 (3)	0.068 (3)	0.000 (2)	0.010 (2)	0.006 (2)
C17	0.048 (3)	0.063 (3)	0.086 (4)	0.003 (2)	−0.010 (3)	0.001 (3)
C18	0.078 (3)	0.056 (3)	0.059 (3)	0.007 (3)	−0.013 (3)	0.007 (2)
C19	0.065 (3)	0.054 (3)	0.052 (3)	−0.006 (2)	0.005 (2)	0.006 (2)
C20	0.054 (3)	0.119 (5)	0.096 (4)	−0.029 (3)	0.014 (3)	−0.009 (4)
C21	0.103 (4)	0.089 (4)	0.054 (3)	0.002 (3)	0.017 (3)	0.001 (3)
C22A	0.156 (6)	0.125 (5)	0.116 (4)	0.008 (4)	0.018 (4)	−0.031 (4)
C23A	0.156 (6)	0.125 (5)	0.116 (4)	0.008 (4)	0.018 (4)	−0.031 (4)
C24	0.070 (3)	0.055 (3)	0.108 (4)	−0.002 (2)	0.006 (3)	0.008 (3)
C23B	0.156 (6)	0.125 (5)	0.116 (4)	0.008 (4)	0.018 (4)	−0.031 (4)
C22B	0.156 (6)	0.125 (5)	0.116 (4)	0.008 (4)	0.018 (4)	−0.031 (4)

Geometric parameters (Å, º) top

S1—O3	1.422 (3)	C11A—H11B	0.9600
S1—O4	1.425 (3)	C11A—H11C	0.9600
S1—N1	1.630 (3)	C11A—H11A	0.9600
S1—C12	1.743 (5)	C11B—H11D	0.9600
S2—O7	1.422 (3)	C11B—H11E	0.9600
S2—O8	1.418 (4)	C11B—H11F	0.9600
S2—N2	1.622 (3)	C12—H12C	0.9600
S2—C24	1.739 (5)	C12—H12A	0.9600
O1—C1	1.187 (6)	C12—H12B	0.9600
O2—C1	1.330 (5)	C13—C14	1.485 (6)
O2—C8	1.449 (5)	C14—C15	1.395 (6)
O5—C13	1.199 (6)	C14—C19	1.384 (6)
O6—C13	1.311 (6)	C15—C16	1.376 (6)
O6—C20	1.449 (5)	C16—C17	1.366 (7)
N1—C7	1.431 (5)	C17—C18	1.361 (7)
N1—C9	1.488 (6)	C18—C19	1.382 (7)
N2—C21	1.486 (6)	C21—C22A	1.465 (16)
N2—C15	1.442 (5)	C21—C22B	1.53 (2)
C1—C2	1.492 (6)	C22A—C23A	1.51 (2)
C2—C3	1.393 (5)	C22B—C23B	1.50 (3)
C2—C7	1.383 (6)	C16—H16	0.9300
C3—C4	1.371 (7)	C17—H17	0.9300
C4—C5	1.381 (7)	C18—H18	0.9300
C5—C6	1.370 (7)	C19—H19	0.9300
C6—C7	1.390 (6)	C20—H20A	0.9600
C9—C10A	1.482 (15)	C20—H20B	0.9600
C9—C10B	1.527 (19)	C20—H20C	0.9600
C10A—C11A	1.546 (19)	C21—H21A	0.9700
C10B—C11B	1.48 (2)	C21—H21B	0.9700
C3—H3	0.9300	C22A—H22A	0.9700
C4—H4	0.9300	C22A—H22B	0.9700
C5—H5	0.9300	C22B—H22D	0.9700
C6—H6	0.9300	C22B—H22C	0.9700
C8—H8C	0.9600	C23A—H23B	0.9600
C8—H8A	0.9600	C23A—H23C	0.9600
C8—H8B	0.9600	C23A—H23A	0.9600
C9—H9B	0.9700	C23B—H23D	0.9600
C9—H9A	0.9700	C23B—H23F	0.9600
C10A—H10A	0.9700	C23B—H23E	0.9600
C10A—H10B	0.9700	C24—H24B	0.9600
C10B—H10C	0.9700	C24—H24C	0.9600
C10B—H10D	0.9700	C24—H24A	0.9600

O3—S1—O4	119.22 (19)	H11D—C11B—H11F	110.00
O3—S1—N1	107.47 (17)	H11E—C11B—H11F	109.00
O3—S1—C12	107.5 (2)	C10B—C11B—H11D	110.00
O4—S1—N1	107.69 (18)	H11D—C11B—H11E	109.00
O4—S1—C12	107.1 (2)	H12B—C12—H12C	109.00
N1—S1—C12	107.4 (2)	S1—C12—H12A	109.00
O7—S2—O8	119.26 (19)	S1—C12—H12B	109.00
O7—S2—N2	107.31 (18)	S1—C12—H12C	109.00
O7—S2—C24	107.4 (2)	H12A—C12—H12B	109.00
O8—S2—N2	107.3 (2)	H12A—C12—H12C	110.00
O8—S2—C24	108.1 (2)	O5—C13—O6	122.3 (4)
N2—S2—C24	106.9 (2)	O5—C13—C14	125.1 (4)
C1—O2—C8	116.0 (4)	O6—C13—C14	112.4 (4)
C13—O6—C20	116.0 (4)	C13—C14—C15	123.2 (4)
S1—N1—C7	118.7 (3)	C13—C14—C19	118.4 (4)
S1—N1—C9	117.8 (3)	C15—C14—C19	118.3 (4)
C7—N1—C9	117.5 (3)	N2—C15—C14	120.3 (3)
S2—N2—C15	117.2 (3)	N2—C15—C16	119.8 (4)
S2—N2—C21	117.9 (3)	C14—C15—C16	120.0 (4)
C15—N2—C21	117.6 (3)	C15—C16—C17	120.7 (4)
O1—C1—O2	123.3 (4)	C16—C17—C18	120.4 (4)
O1—C1—C2	125.7 (4)	C17—C18—C19	119.8 (5)
O2—C1—C2	110.9 (4)	C14—C19—C18	120.9 (4)
C1—C2—C3	118.3 (3)	N2—C21—C22A	106.0 (7)
C1—C2—C7	122.3 (3)	N2—C21—C22B	117.1 (9)
C3—C2—C7	119.3 (4)	C21—C22A—C23A	116.7 (11)
C2—C3—C4	121.1 (4)	C21—C22B—C23B	109.7 (14)
C3—C4—C5	119.4 (5)	C15—C16—H16	120.00
C4—C5—C6	120.2 (4)	C17—C16—H16	120.00
C5—C6—C7	120.9 (4)	C16—C17—H17	120.00
C2—C7—C6	119.2 (4)	C18—C17—H17	120.00
N1—C7—C6	119.1 (4)	C17—C18—H18	120.00
N1—C7—C2	121.7 (4)	C19—C18—H18	120.00
N1—C9—C10A	120.2 (7)	C14—C19—H19	119.00
N1—C9—C10B	103.5 (8)	C18—C19—H19	120.00
C9—C10A—C11A	100.9 (10)	O6—C20—H20A	110.00
C9—C10B—C11B	123.0 (16)	O6—C20—H20B	109.00
C2—C3—H3	119.00	O6—C20—H20C	109.00
C4—C3—H3	119.00	H20A—C20—H20B	109.00
C3—C4—H4	120.00	H20A—C20—H20C	109.00
C5—C4—H4	120.00	H20B—C20—H20C	109.00
C6—C5—H5	120.00	N2—C21—H21A	111.00
C4—C5—H5	120.00	N2—C21—H21B	111.00
C5—C6—H6	120.00	C22A—C21—H21A	111.00
C7—C6—H6	120.00	C22A—C21—H21B	111.00
O2—C8—H8B	110.00	H21A—C21—H21B	109.00
O2—C8—H8A	109.00	C22B—C21—H21A	126.00
H8B—C8—H8C	109.00	C22B—C21—H21B	78.00
H8A—C8—H8C	109.00	C21—C22A—H22A	108.00
O2—C8—H8C	109.00	C21—C22A—H22B	108.00
H8A—C8—H8B	109.00	C23A—C22A—H22A	108.00
N1—C9—H9A	107.00	C23A—C22A—H22B	108.00
N1—C9—H9B	107.00	H22A—C22A—H22B	107.00
C10A—C9—H9A	107.00	C23B—C22B—H22D	110.00
C10A—C9—H9B	107.00	H22C—C22B—H22D	108.00
C10B—C9—H9A	131.00	C21—C22B—H22C	110.00
C10B—C9—H9B	99.00	C21—C22B—H22D	110.00
H9A—C9—H9B	107.00	C23B—C22B—H22C	110.00
C9—C10A—H10A	112.00	C22A—C23A—H23C	109.00
C11A—C10A—H10A	112.00	H23A—C23A—H23B	110.00
C11A—C10A—H10B	112.00	H23A—C23A—H23C	109.00
C9—C10A—H10B	112.00	C22A—C23A—H23A	109.00
H10A—C10A—H10B	109.00	C22A—C23A—H23B	109.00
C9—C10B—H10C	107.00	H23B—C23A—H23C	109.00
C9—C10B—H10D	107.00	C22B—C23B—H23D	109.00
H10C—C10B—H10D	107.00	C22B—C23B—H23E	109.00
C11B—C10B—H10D	106.00	H23D—C23B—H23F	109.00
C11B—C10B—H10C	107.00	H23E—C23B—H23F	109.00
H11A—C11A—H11C	109.00	C22B—C23B—H23F	109.00
H11B—C11A—H11C	109.00	H23D—C23B—H23E	110.00
C10A—C11A—H11B	109.00	S2—C24—H24C	110.00
C10A—C11A—H11A	109.00	H24B—C24—H24C	110.00
H11A—C11A—H11B	109.00	H24A—C24—H24B	109.00
C10A—C11A—H11C	109.00	H24A—C24—H24C	109.00
C10B—C11B—H11E	109.00	S2—C24—H24A	109.00
C10B—C11B—H11F	110.00	S2—C24—H24B	109.00

O3—S1—N1—C7	38.0 (3)	O1—C1—C2—C7	−40.1 (7)
O3—S1—N1—C9	−170.0 (3)	O2—C1—C2—C3	−40.3 (5)
O4—S1—N1—C7	167.6 (3)	C1—C2—C7—C6	176.5 (4)
O4—S1—N1—C9	−40.4 (3)	C1—C2—C3—C4	−174.5 (4)
C12—S1—N1—C7	−77.4 (3)	C7—C2—C3—C4	1.7 (7)
C12—S1—N1—C9	74.6 (3)	C1—C2—C7—N1	−4.3 (7)
C24—S2—N2—C21	−76.9 (4)	C3—C2—C7—N1	179.7 (4)
O8—S2—N2—C15	−171.7 (3)	C3—C2—C7—C6	0.6 (7)
O7—S2—N2—C15	−42.4 (3)	C2—C3—C4—C5	−2.2 (7)
O7—S2—N2—C21	168.1 (3)	C3—C4—C5—C6	0.6 (7)
O8—S2—N2—C21	38.8 (4)	C4—C5—C6—C7	1.6 (7)
C24—S2—N2—C15	72.6 (3)	C5—C6—C7—C2	−2.1 (7)
C8—O2—C1—C2	178.1 (4)	C5—C6—C7—N1	178.7 (4)
C8—O2—C1—O1	1.8 (6)	N1—C9—C10A—C11A	−74.2 (11)
C20—O6—C13—O5	2.2 (7)	O5—C13—C14—C15	35.4 (7)
C20—O6—C13—C14	−173.4 (4)	O5—C13—C14—C19	−140.6 (5)
S1—N1—C7—C6	103.8 (4)	O6—C13—C14—C15	−149.2 (4)
C9—N1—C7—C2	132.5 (4)	O6—C13—C14—C19	34.9 (6)
C9—N1—C7—C6	−48.3 (5)	C13—C14—C15—N2	5.8 (6)
S1—N1—C9—C10A	146.0 (7)	C13—C14—C15—C16	−175.2 (4)
C7—N1—C9—C10A	−61.7 (8)	C19—C14—C15—N2	−178.3 (4)
S1—N1—C7—C2	−75.4 (5)	C19—C14—C15—C16	0.8 (6)
C15—N2—C21—C22A	95.0 (7)	C13—C14—C19—C18	174.2 (4)
S2—N2—C15—C14	83.4 (4)	C15—C14—C19—C18	−2.0 (7)
S2—N2—C15—C16	−95.7 (4)	N2—C15—C16—C17	179.3 (4)
C21—N2—C15—C14	−127.0 (4)	C14—C15—C16—C17	0.2 (7)
C21—N2—C15—C16	53.9 (6)	C15—C16—C17—C18	0.0 (7)
S2—N2—C21—C22A	−115.6 (7)	C16—C17—C18—C19	−1.2 (7)
O1—C1—C2—C3	135.9 (5)	C17—C18—C19—C14	2.2 (7)
O2—C1—C2—C7	143.7 (4)	N2—C21—C22A—C23A	−170.3 (10)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C2–C7 and C14–C19 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O8ⁱ	0.93	2.59	3.483 (6)	161
C11A—H11C···O1	0.96	2.57	3.486 (15)	159
C16—H16···O4	0.93	2.51	3.429 (5)	168
C20—H20C···O3ⁱⁱ	0.96	2.57	3.172 (6)	121
C21—H21A···O1	0.97	2.55	3.192 (6)	124
C12—H12A···Cg2ⁱⁱⁱ	0.96	2.84	3.660 (5)	144
C18—H18···Cg1^iv	0.93	2.87	3.588 (5)	135

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₇NO₄S
M_r	271.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.1762 (4), 15.0178 (6), 18.0900 (8)
β (°)	92.787 (2)
V (Å³)	2761.3 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.25 × 0.12 × 0.10

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.955, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	25991, 5409, 2607
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.193, 1.01
No. of reflections	5409
No. of parameters	328
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.40

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), 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

Cg1 and Cg2 are the centroids of the C2–C7 and C14–C19 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O8ⁱ	0.93	2.59	3.483 (6)	161
C11A—H11C···O1	0.96	2.57	3.486 (15)	159
C16—H16···O4	0.93	2.51	3.429 (5)	168
C20—H20C···O3ⁱⁱ	0.96	2.57	3.172 (6)	121
C21—H21A···O1	0.97	2.55	3.192 (6)	124
C12—H12A···Cg2ⁱⁱⁱ	0.96	2.84	3.660 (5)	144
C18—H18···Cg1^iv	0.93	2.87	3.588 (5)	135

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

Acknowledgements

MS gratefully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing a Scholarship under the Indigenous PhD Program (PIN 042–120567-PS2–276).

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). 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
Shafiq, M., Tahir, M. N., Khan, I. U., Arshad, M. N. & Haider, Z. (2009a). Acta Cryst. E65, o1413. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shafiq, M., Tahir, M. N., Khan, I. U., Arshad, M. N. & Khan, M. H. (2009b). Acta Cryst. E65, o955. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shafiq, M., Tahir, M. N., Khan, I. U., Siddiqui, W. A. & Arshad, M. N. (2008). Acta Cryst. E64, o389. Web of Science CSD CrossRef IUCr Journals 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

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