2-{1-[(2-Nitro­benzene­sulfonamido)­meth­yl]cyclo­hexyl}acetic acid

Kanwal, N.; Akbar Hussain, E.; Şahin, O.; Büyükgüngör, O.

doi:10.1107/S160053681105224X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o86

doi:10.1107/S160053681105224X

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2-{1-[(2-Nitrobenzenesulfonamido)methyl]cyclohexyl}acetic acid

Nosheen Kanwal,^a ^* Erum Akbar Hussain,^a Onur Şahin ^b and Orhan Büyükgüngör ^b

^aDepartment of Chemistry, Lahore College for Women University, Lahore 54000, Pakistan, and ^bDepartment of Physics, Ondokuz Mayıs University, TR-55139 Samsun, Turkey
^*Correspondence e-mail: nosheen.chem.lcwu@gmail.com

(Received 2 December 2011; accepted 3 December 2011; online 10 December 2011)

In the title compound, C₁₅H₂₀N₂O₆S, the C—SO₂—NH—C torsion angle is 64.54 (14)°. In the molecule, there is a bifurcated N—H⋯(O,O) hydrogen bond, forming S(7) rings. In the crystal, inversion dimers are formed via O—H⋯O hydrogen bonds involving the carboxyl group, so forming R₂²(8) rings. These dimers are further linked via pairs of C—H⋯O hydrogen bonds, forming a C(6) chain propagating along the c-axis direction.

Related literature

For commercial uses of gabapentin {systematic name: 2-[1-(aminomethyl)cyclohexyl]acetic acid}, see: Taylor et al. (1998 ); Cesena & Calcutt (1999 ); Field et al. (2000 ). For the ability of gabapentin to inhibit voltage-dependent Ca²⁺ channel currents, see: Stefani et al. (1998 ); Walker & De Waard (1998 ); Martin et al. (2000 ); Sutton et al. (2002 ). For the graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₅H₂₀N₂O₆S
M_r = 356.39
Monoclinic, P 2₁ /c
a = 7.7383 (2) Å
b = 20.7319 (5) Å
c = 11.9460 (3) Å
β = 116.869 (1)°
V = 1709.59 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.37 × 0.33 × 0.32 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
17069 measured reflections
4247 independent reflections
3202 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.110
S = 1.02
4247 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.790 (19)	2.362 (19)	2.978 (2)	135.6 (18)
N1—H1⋯O6	0.790 (19)	2.455 (19)	3.050 (2)	133.0 (18)
O5—H5⋯O6ⁱ	0.82	1.85	2.6595 (18)	168
C12—H12⋯O2ⁱⁱ	0.93	2.50	3.339 (2)	151
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681105224X/su2343sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681105224X/su2343Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681105224X/su2343Isup3.cml

checkCIF report

Comment top

The gabapentin, (systematic name: 2-[1-(aminomethyl)cyclohexyl]acetic acid), is used commercially as an anti-convulsant drug and was originally developed for the treatment of spasticity and partial epilepsy (Taylor et al., 1998; Cesena & Calcutt, 1999; Field et al., 2000). Various studies have been undertaken to investigate possible mechanisms of this drug's action. Stefani et al. (1998) were the first to demonstrate that gabapentin inhibits voltage-dependent Ca²⁺ channel currents recorded from cortical neurons. This ability of gabapentin to inhibit Ca²⁺ channels has also been demonstrated by number of other groups (Walker & De Waard, 1998; Martin et al., 2000; Sutton et al. 2002). However, the drug has poor oral bioavailability and is difficult to synthesize hence, SAR and structural studies on new derivatives of gabapentin is an attractive area of research in medicinal chemistry. Herein, we report on an efficient synthesis and the crystal structure of a new sulfonamide derivative of gabapentin.

The molecular structure of the title compound is shown in Fig. 1. The conformation of the N1—C9 bond in the C—SO₂—NH—C segment has gauche torsions with respect to the S═O bonds. The molecules are twisted at the S1 atom with the C10—S1—N1—C9 torsional angle being 64.54 (14)°. The dihedral angle between the sulfonyl benzene ring and the –SO₂—NH—C (S1,N1,C9) segment is 86.07 (14)°. The values of the ring puckering parameters: Q_T = 0.555 (2) Å, θ = 175.8 (2)° and ϕ = 328 (3)° (Cremer & Pople, 1975), indicate that the cyclohexane ring has a chair conformation. As shown in Fig. 1 and Table 1, bifurcated intramolecular N1—H1···O3 and N1—H1···O6 hydrogen bonds produce S(7) rings (Bernstein et al., 1995).

In the crystal, hydroxyl O5 acts as a hydrogen-bond donor to the carbonly O atom, O6ⁱ, so forming an inversion dimer with an R₂²(8) ring (Table 1 and Fig. 2). As shown in Fig. 2, these dimers are further linked via a C-H···O interaction, so forming a C(6) chain running parallel to [001].

Related literature top

For commercial uses of gabapentin {systematic name: 2-[1-(aminomethyl)cyclohexyl]acetic acid}, see: Taylor et al. (1998); Cesena & Calcutt (1999); Field et al. (2000). For the ability of gabapentin to inhibit voltage-dependent Ca²⁺ channel currents, see: Stefani et al. (1998); Walker & De Waard (1998); Martin et al. (2000); Sutton et al. (2002). For the graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

Gabapentin (0.171 g, 1.00 mmol) was dissolved in distilled water (10 ml) in a round bottom flask (25 ml). The pH of the solution was maintained at 8–9 using 1 M Na2CO3 solution. The 2-nitrobenzenesulfonyl chloride (0.221 g, 1.00 mmol) was added to the above solution and stirred at room temperature. The reaction completion was monitored by TLC. Upon completion of the reaction the pH was adjusted 1–2, using 1 M HCl solution. The precipitate obtained was filtered, washed with distilled water, dried and recrystallized from methanol to yield colourless crystals.

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 Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A view of the molecular structure of the title molecule, showing displacement ellipsoids drawn at the 30% probability level. Hydrogen bonds are indicated by dashed lines.
	Fig. 2. A view of the crystal packing of the title compound, showing the formation of the R₂²(8) rings, and the C(7) chain. For the sake of clarity, H atoms not involved in these motifs have been omitted [Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, -y+1/2, z-1/2; see Table 1 for further details].

2-{1-[(2-Nitrobenzenesulfonamido)methyl]cyclohexyl}acetic acid top

Crystal data top

C₁₅H₂₀N₂O₆S	F(000) = 752
M_r = 356.39	D_x = 1.385 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5311 reflections
a = 7.7383 (2) Å	θ = 2.9–27.2°
b = 20.7319 (5) Å	µ = 0.22 mm⁻¹
c = 11.9460 (3) Å	T = 296 K
β = 116.869 (1)°	Block, colourless
V = 1709.59 (7) Å³	0.37 × 0.33 × 0.32 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3202 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 28.3°, θ_min = 2.0°
phi and ω scans	h = −10→10
17069 measured reflections	k = −27→27
4247 independent reflections	l = −15→15

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0492P)² + 0.4452P] where P = (F_o² + 2F_c²)/3
4247 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₅H₂₀N₂O₆S	V = 1709.59 (7) Å³
M_r = 356.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7383 (2) Å	µ = 0.22 mm⁻¹
b = 20.7319 (5) Å	T = 296 K
c = 11.9460 (3) Å	0.37 × 0.33 × 0.32 mm
β = 116.869 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3202 reflections with I > 2σ(I)
17069 measured reflections	R_int = 0.022
4247 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.29 e Å⁻³
4247 reflections	Δρ_min = −0.32 e Å⁻³
221 parameters

Special details top

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
C1	0.2548 (2)	0.54510 (7)	0.24581 (13)	0.0348 (3)
C2	0.1197 (2)	0.59198 (8)	0.14519 (15)	0.0438 (4)
H2A	0.1787	0.6344	0.1619	0.053*
H2B	0.1059	0.5781	0.0640	0.053*
C3	−0.0799 (3)	0.59682 (9)	0.13939 (18)	0.0553 (4)
H3A	−0.1568	0.6283	0.0765	0.066*
H3B	−0.1449	0.5554	0.1153	0.066*
C4	−0.0631 (3)	0.61664 (10)	0.2658 (2)	0.0656 (5)
H4A	−0.0060	0.6593	0.2871	0.079*
H4B	−0.1912	0.6185	0.2615	0.079*
C5	0.0607 (3)	0.56932 (10)	0.36644 (19)	0.0638 (5)
H5A	−0.0033	0.5277	0.3493	0.077*
H5B	0.0743	0.5841	0.4471	0.077*
C6	0.2613 (3)	0.56180 (9)	0.37290 (15)	0.0498 (4)
H6A	0.3309	0.5281	0.4327	0.060*
H6B	0.3327	0.6017	0.4036	0.060*
C7	0.4633 (2)	0.55220 (8)	0.26081 (15)	0.0441 (4)
H7A	0.5016	0.5971	0.2766	0.053*
H7B	0.5509	0.5275	0.3333	0.053*
C8	0.4837 (2)	0.52997 (8)	0.14850 (17)	0.0453 (4)
C9	0.1812 (2)	0.47606 (7)	0.20560 (14)	0.0371 (3)
H9A	0.0581	0.4708	0.2075	0.045*
H9B	0.1595	0.4694	0.1199	0.045*
C10	0.0958 (2)	0.31795 (7)	0.19092 (14)	0.0377 (3)
C11	0.1750 (2)	0.27787 (7)	0.13323 (14)	0.0408 (3)
C12	0.0613 (3)	0.23949 (8)	0.03334 (17)	0.0548 (4)
H12	0.1174	0.2125	−0.0034	0.066*
C13	−0.1371 (3)	0.24136 (10)	−0.01188 (19)	0.0648 (5)
H13	−0.2155	0.2159	−0.0802	0.078*
C14	−0.2189 (3)	0.28022 (10)	0.0429 (2)	0.0632 (5)
H14	−0.3528	0.2813	0.0116	0.076*
C15	−0.1039 (2)	0.31806 (8)	0.14452 (18)	0.0510 (4)
H15	−0.1610	0.3439	0.1823	0.061*
N1	0.3172 (2)	0.42711 (6)	0.28645 (14)	0.0441 (3)
H1	0.398 (3)	0.4174 (9)	0.2660 (18)	0.054 (6)*
N2	0.3849 (2)	0.27452 (7)	0.17499 (14)	0.0516 (4)
O1	0.4004 (2)	0.32564 (6)	0.40392 (11)	0.0645 (4)
O2	0.1074 (2)	0.38599 (6)	0.37366 (13)	0.0643 (4)
O3	0.47073 (19)	0.32459 (7)	0.18100 (16)	0.0724 (4)
O4	0.4618 (2)	0.22220 (7)	0.19748 (17)	0.0839 (5)
O5	0.4434 (2)	0.56977 (6)	0.05920 (13)	0.0641 (4)
H5	0.4596	0.5525	0.0030	0.096*
O6	0.5377 (2)	0.47314 (6)	0.14477 (13)	0.0626 (4)
S1	0.23737 (6)	0.364280 (19)	0.32720 (4)	0.04464 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0359 (7)	0.0320 (7)	0.0359 (7)	−0.0062 (6)	0.0158 (6)	−0.0050 (6)
C2	0.0451 (9)	0.0381 (8)	0.0469 (9)	−0.0023 (7)	0.0198 (7)	0.0030 (7)
C3	0.0440 (9)	0.0509 (10)	0.0682 (12)	0.0051 (8)	0.0230 (9)	0.0021 (9)
C4	0.0558 (11)	0.0621 (12)	0.0900 (15)	−0.0012 (9)	0.0428 (11)	−0.0182 (11)
C5	0.0784 (13)	0.0681 (13)	0.0635 (12)	−0.0116 (11)	0.0485 (11)	−0.0197 (10)
C6	0.0591 (10)	0.0487 (9)	0.0400 (8)	−0.0074 (8)	0.0210 (8)	−0.0110 (7)
C7	0.0372 (8)	0.0401 (8)	0.0523 (9)	−0.0092 (6)	0.0177 (7)	−0.0065 (7)
C8	0.0384 (8)	0.0411 (9)	0.0626 (10)	−0.0053 (7)	0.0283 (8)	0.0014 (7)
C9	0.0385 (7)	0.0343 (7)	0.0366 (7)	−0.0066 (6)	0.0152 (6)	−0.0046 (6)
C10	0.0450 (8)	0.0285 (7)	0.0408 (8)	−0.0020 (6)	0.0206 (7)	0.0038 (6)
C11	0.0466 (8)	0.0328 (7)	0.0427 (8)	0.0001 (6)	0.0200 (7)	0.0026 (6)
C12	0.0744 (12)	0.0411 (9)	0.0476 (9)	−0.0029 (8)	0.0265 (9)	−0.0061 (7)
C13	0.0679 (13)	0.0529 (11)	0.0524 (11)	−0.0158 (10)	0.0084 (10)	−0.0034 (9)
C14	0.0453 (10)	0.0577 (12)	0.0723 (13)	−0.0093 (9)	0.0140 (9)	0.0066 (10)
C15	0.0471 (9)	0.0443 (9)	0.0654 (11)	−0.0011 (7)	0.0287 (8)	0.0048 (8)
N1	0.0445 (8)	0.0330 (7)	0.0547 (8)	−0.0023 (6)	0.0223 (7)	0.0002 (6)
N2	0.0531 (8)	0.0444 (8)	0.0598 (9)	0.0074 (7)	0.0277 (7)	−0.0005 (7)
O1	0.0750 (9)	0.0464 (7)	0.0474 (7)	0.0032 (6)	0.0059 (6)	0.0072 (6)
O2	0.1011 (11)	0.0500 (7)	0.0670 (8)	−0.0077 (7)	0.0603 (8)	−0.0054 (6)
O3	0.0548 (8)	0.0564 (8)	0.1159 (13)	−0.0022 (6)	0.0474 (8)	−0.0012 (8)
O4	0.0726 (10)	0.0507 (8)	0.1188 (14)	0.0237 (7)	0.0347 (9)	0.0021 (8)
O5	0.0783 (9)	0.0592 (8)	0.0755 (9)	0.0146 (7)	0.0530 (8)	0.0136 (7)
O6	0.0811 (9)	0.0444 (7)	0.0816 (9)	0.0067 (6)	0.0537 (8)	0.0045 (6)
S1	0.0601 (3)	0.0345 (2)	0.0397 (2)	−0.00341 (17)	0.02283 (19)	0.00003 (15)

Geometric parameters (Å, º) top

C1—C2	1.532 (2)	C9—N1	1.467 (2)
C1—C9	1.5350 (19)	C9—H9A	0.9700
C1—C6	1.536 (2)	C9—H9B	0.9700
C1—C7	1.548 (2)	C10—C15	1.386 (2)
C2—C3	1.518 (2)	C10—C11	1.387 (2)
C2—H2A	0.9700	C10—S1	1.7779 (15)
C2—H2B	0.9700	C11—C12	1.372 (2)
C3—C4	1.513 (3)	C11—N2	1.470 (2)
C3—H3A	0.9700	C12—C13	1.379 (3)
C3—H3B	0.9700	C12—H12	0.9300
C4—C5	1.512 (3)	C13—C14	1.360 (3)
C4—H4A	0.9700	C13—H13	0.9300
C4—H4B	0.9700	C14—C15	1.380 (3)
C5—C6	1.527 (3)	C14—H14	0.9300
C5—H5A	0.9700	C15—H15	0.9300
C5—H5B	0.9700	N1—S1	1.6084 (14)
C6—H6A	0.9700	N1—H1	0.790 (19)
C6—H6B	0.9700	N2—O4	1.2077 (19)
C7—C8	1.493 (2)	N2—O3	1.2167 (19)
C7—H7A	0.9700	O1—S1	1.4244 (13)
C7—H7B	0.9700	O2—S1	1.4240 (13)
C8—O6	1.258 (2)	O5—H5	0.8200
C8—O5	1.271 (2)

C2—C1—C9	108.72 (12)	H7A—C7—H7B	107.7
C2—C1—C6	109.79 (13)	O6—C8—O5	122.54 (16)
C9—C1—C6	111.18 (12)	O6—C8—C7	119.54 (15)
C2—C1—C7	109.67 (12)	O5—C8—C7	117.92 (15)
C9—C1—C7	110.16 (12)	N1—C9—C1	112.64 (12)
C6—C1—C7	107.29 (12)	N1—C9—H9A	109.1
C3—C2—C1	113.41 (13)	C1—C9—H9A	109.1
C3—C2—H2A	108.9	N1—C9—H9B	109.1
C1—C2—H2A	108.9	C1—C9—H9B	109.1
C3—C2—H2B	108.9	H9A—C9—H9B	107.8
C1—C2—H2B	108.9	C15—C10—C11	117.76 (15)
H2A—C2—H2B	107.7	C15—C10—S1	118.65 (13)
C4—C3—C2	110.23 (15)	C11—C10—S1	123.43 (12)
C4—C3—H3A	109.6	C12—C11—C10	121.73 (16)
C2—C3—H3A	109.6	C12—C11—N2	116.35 (15)
C4—C3—H3B	109.6	C10—C11—N2	121.92 (14)
C2—C3—H3B	109.6	C11—C12—C13	119.16 (18)
H3A—C3—H3B	108.1	C11—C12—H12	120.4
C5—C4—C3	110.83 (15)	C13—C12—H12	120.4
C5—C4—H4A	109.5	C14—C13—C12	120.38 (18)
C3—C4—H4A	109.5	C14—C13—H13	119.8
C5—C4—H4B	109.5	C12—C13—H13	119.8
C3—C4—H4B	109.5	C13—C14—C15	120.32 (18)
H4A—C4—H4B	108.1	C13—C14—H14	119.8
C4—C5—C6	111.75 (16)	C15—C14—H14	119.8
C4—C5—H5A	109.3	C14—C15—C10	120.63 (17)
C6—C5—H5A	109.3	C14—C15—H15	119.7
C4—C5—H5B	109.3	C10—C15—H15	119.7
C6—C5—H5B	109.3	C9—N1—S1	120.04 (11)
H5A—C5—H5B	107.9	C9—N1—H1	113.8 (14)
C5—C6—C1	113.24 (14)	S1—N1—H1	110.6 (14)
C5—C6—H6A	108.9	O4—N2—O3	123.53 (16)
C1—C6—H6A	108.9	O4—N2—C11	118.41 (15)
C5—C6—H6B	108.9	O3—N2—C11	118.01 (14)
C1—C6—H6B	108.9	C8—O5—H5	109.5
H6A—C6—H6B	107.7	O2—S1—O1	120.24 (9)
C8—C7—C1	113.23 (12)	O2—S1—N1	107.30 (8)
C8—C7—H7A	108.9	O1—S1—N1	107.49 (8)
C1—C7—H7A	108.9	O2—S1—C10	106.03 (8)
C8—C7—H7B	108.9	O1—S1—C10	106.58 (7)
C1—C7—H7B	108.9	N1—S1—C10	108.81 (7)

C9—C1—C2—C3	69.39 (17)	C10—C11—C12—C13	0.8 (3)
C6—C1—C2—C3	−52.45 (18)	N2—C11—C12—C13	−178.76 (16)
C7—C1—C2—C3	−170.10 (13)	C11—C12—C13—C14	−0.8 (3)
C1—C2—C3—C4	57.0 (2)	C12—C13—C14—C15	−0.2 (3)
C2—C3—C4—C5	−57.7 (2)	C13—C14—C15—C10	1.2 (3)
C3—C4—C5—C6	56.3 (2)	C11—C10—C15—C14	−1.1 (2)
C4—C5—C6—C1	−53.1 (2)	S1—C10—C15—C14	−176.65 (14)
C2—C1—C6—C5	50.00 (18)	C1—C9—N1—S1	139.40 (12)
C9—C1—C6—C5	−70.36 (18)	C12—C11—N2—O4	−52.4 (2)
C7—C1—C6—C5	169.12 (15)	C10—C11—N2—O4	128.05 (18)
C2—C1—C7—C8	−67.57 (17)	C12—C11—N2—O3	125.20 (18)
C9—C1—C7—C8	52.07 (17)	C10—C11—N2—O3	−54.3 (2)
C6—C1—C7—C8	173.23 (14)	C9—N1—S1—O2	−49.77 (14)
C1—C7—C8—O6	−94.18 (18)	C9—N1—S1—O1	179.59 (12)
C1—C7—C8—O5	85.21 (18)	C9—N1—S1—C10	64.54 (14)
C2—C1—C9—N1	171.39 (13)	C15—C10—S1—O2	8.75 (15)
C6—C1—C9—N1	−67.63 (17)	C11—C10—S1—O2	−166.48 (13)
C7—C1—C9—N1	51.19 (17)	C15—C10—S1—O1	137.98 (13)
C15—C10—C11—C12	0.2 (2)	C11—C10—S1—O1	−37.26 (15)
S1—C10—C11—C12	175.44 (13)	C15—C10—S1—N1	−106.38 (13)
C15—C10—C11—N2	179.68 (14)	C11—C10—S1—N1	78.38 (14)
S1—C10—C11—N2	−5.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.790 (19)	2.362 (19)	2.978 (2)	135.6 (18)
N1—H1···O6	0.790 (19)	2.455 (19)	3.050 (2)	133.0 (18)
O5—H5···O6ⁱ	0.82	1.85	2.6595 (18)	168
C12—H12···O2ⁱⁱ	0.93	2.50	3.339 (2)	151

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

Experimental details

Crystal data
Chemical formula	C₁₅H₂₀N₂O₆S
M_r	356.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.7383 (2), 20.7319 (5), 11.9460 (3)
β (°)	116.869 (1)
V (Å³)	1709.59 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.37 × 0.33 × 0.32

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	17069, 4247, 3202
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.110, 1.02
No. of reflections	4247
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)	0.29, −0.32

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.790 (19)	2.362 (19)	2.978 (2)	135.6 (18)
N1—H1···O6	0.790 (19)	2.455 (19)	3.050 (2)	133.0 (18)
O5—H5···O6ⁱ	0.82	1.85	2.6595 (18)	168
C12—H12···O2ⁱⁱ	0.93	2.50	3.339 (2)	151

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

Acknowledgements

The authors are grateful to the Department of Chemistry, GC University Lahore, Pakistan, for providing the diffractometer facility.

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