N-[2-(3,4-Dimeth­oxy­phen­yl)eth­yl]-N-methyl­benzene­sulfonamide

Vennila, J.P.; Thiruvadigal, D.J.; Kamala, E.T.S.; Kavitha, H.P.; Manivannan, V.

doi:10.1107/S1600536812005272

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o882

doi:10.1107/S1600536812005272

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N-[2-(3,4-Dimethoxyphenyl)ethyl]-N-methylbenzenesulfonamide

Jasmine P. Vennila,^a ^* D. John Thiruvadigal,^b E. Theboral Sugi Kamala,^c Helen P. Kavitha ^d and V. Manivannan ^e

^aDepartment of Physics, Panimalar Institute of Technology, Chennai 602 103, India, ^bDepartment of Physics, SRM University, Kattankulathur Campus, Chennai 603 203, India, ^cDepartment of Physics, Easwari Engineering College, Ramapuram, Chennai 600 089, India, ^dDepartment of Chemistry, SRM University, Ramapuram Campus, Chennai 600 089, India, and ^eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, India
^*Correspondence e-mail: jasprabhu1@yahoo.co.in

(Received 27 January 2012; accepted 6 February 2012; online 29 February 2012)

In the title compound, C₁₇H₂₁NO₄S, the phenyl and dimethoxyphenyl rings are almost perpendicular to each other, making a dihedral angle of 82.57 (5)°. The structure is stabilized by intermolecular C—H⋯O interactions and the packing is further enhanced by C—H ⋯π interactions.

Related literature

For the biological activity of sulfonamide derivatives, see: Zareef et al. (2007 ); Pomarnacka & Kozlarska-Kedra (2003 ); Siddiqui et al. (2007 ); Gennarte et al. (1994 ). For standard bond distances, see: Allen et al. (1987 ). For geometric parameters, see: Khan et al. (2010 ). For asymmetry parameters, see: Nardelli (1983 ).

Experimental

Crystal data

C₁₇H₂₁NO₄S
M_r = 335.41
Monoclinic, P 2₁ /c
a = 9.9383 (3) Å
b = 14.6494 (4) Å
c = 12.0097 (3) Å
β = 108.535 (1)°
V = 1657.80 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.40 × 0.40 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.879, T_max = 0.938
20493 measured reflections
4353 independent reflections
3342 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.115
S = 1.00
4353 reflections
212 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the phenyl plane C10–C15.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2ⁱ	0.93	2.60	3.380 (2)	142
C8—H8A⋯O3ⁱⁱ	0.97	2.71	3.620 (2)	156
C4—H4⋯O1ⁱⁱⁱ	0.93	2.65	3.369 (2)	135
C3—H3⋯Cg2^iv	0.93	2.91	3.661 (2)	139
C6—H6⋯Cg2ⁱⁱ	0.93	3.05	3.827 (8)	123
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); 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: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812005272/sj5187sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005272/sj5187Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005272/sj5187Isup3.cml

checkCIF report

Comment top

Sulfonamides exhibit a wide vareity of pharmocological activities such as antibacterial, antitumour, anti-carbonic anhydrase, diuretic hypoglycaemic, antithyroid and protease inhibitory activity. Sulfonamides have also been used clinically as antimalarial agents (Zareef et al., 2007). Sulfonamide derivatives are known to exhibit anticancer and HIV activities (Pomarnacka & Kozlarska-Kedra, 2003). They are also used as anti-convulsants (Siddiqui et al., 2007) and for the treatment of inflammatory rheumatic & non-rheumatic processes (Gennarte et al., 1994).

Fig. 1 shows the structure of compound (I). Bond lengths are comparable with other reported values (Allen et al., 1987).

In the title compound (I) the geometric parameters are similar with those of a similar structure (Khan et al., 2010). The phenyl rings are almost perpendicular to each other making a dihedral angle of 82.57 (5)°. The sum of bond angles around N atom [345.31°] indicates sp² hybridization. The asymmetry parameters for the phenyl rings C1—C6 and C10—C15 are given by Δ_s (C2) = 0.46°, Δ₂ (C1) = 0.28°, Δ_s (C12) = 0.32° and Δ₂ (C11) = 0.22° [Nardelli, 1983]. The crystal packing shows that the molecules are linked into a three dimensional framework through intermolecular C14—H14···02, C8—H8A···03 and C4—H4···01 hydrogen bonds . The packing is further stabilized by C3—H3···Cg(2) and C6—H6···Cg(2) C—H··· π interactions. [Cg(2) is the centroid of the C10—C15 ring], with a distances 3.661 (2)Å and 3.827 (8) Å respectively.

Related literature top

For the biological activity of sulfonamide derivatives, see: Zareef et al. (2007); Pomarnacka & Kozlarska-Kedra (2003); Siddiqui et al. (2007); Gennarte et al. (1994). For standard bond distances, see: Allen et al. (1987). For geometric parameters, see: Khan et al. (2010). For asymmetry parameters, see: Nardelli (1983).

Experimental top

2-(3,4-dimethoxyphenyl)-N-methyl ethanamine (5 mmol) was dissolved in dichloromethane (20 ml) in a round bottom flask. To this, triethylamine (10.2 mmol) was added with stirring for 5 minutes. Then benzenesulfonyl chloride (51 mmol) was added into the reaction mixture and heated to 50 °C for 6 hrs. After cooling the reaction mixture to the ambient temperature, it was added to water (20 ml). The aqueous layer was separated. The ethyl acetate layer was washed twice with 10% sodium chloride solution. The organic layer was dried over 2 g of anhydrous sodium sulfate and filtered. The filtrate was evaporated under vacuum to isolate the crude compound. Recrystallization of the compound using ethyl acetate and hexane mixture yielded diffraction quality crystals.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); 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: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids.
	Fig. 2. The packing of the molecules viewed along b axis.

N-[2-(3,4-Dimethoxyphenyl)ethyl]-N-methylbenzenesulfonamide top

Crystal data top

C₁₇H₂₁NO₄S	F(000) = 712
M_r = 335.41	D_x = 1.344 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7936 reflections
a = 9.9383 (3) Å	θ = 2.2–29.0°
b = 14.6494 (4) Å	µ = 0.22 mm⁻¹
c = 12.0097 (3) Å	T = 293 K
β = 108.535 (1)°	Block, colourless
V = 1657.80 (8) Å³	0.40 × 0.40 × 0.30 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4353 independent reflections
Radiation source: fine-focus sealed tube	3342 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω and ϕ scans	θ_max = 29.2°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→8
T_min = 0.879, T_max = 0.938	k = −19→19
20493 measured reflections	l = −16→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.0586P)² + 0.383P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
4353 reflections	Δρ_max = 0.27 e Å⁻³
212 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (10)

Crystal data top

C₁₇H₂₁NO₄S	V = 1657.80 (8) Å³
M_r = 335.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9383 (3) Å	µ = 0.22 mm⁻¹
b = 14.6494 (4) Å	T = 293 K
c = 12.0097 (3) Å	0.40 × 0.40 × 0.30 mm
β = 108.535 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4353 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3342 reflections with I > 2σ(I)
T_min = 0.879, T_max = 0.938	R_int = 0.028
20493 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.00	Δρ_max = 0.27 e Å⁻³
4353 reflections	Δρ_min = −0.30 e Å⁻³
212 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	0.11829 (14)	0.66352 (10)	0.73921 (12)	0.0389 (3)
C2	−0.02018 (16)	0.69298 (11)	0.71549 (15)	0.0503 (4)
H2	−0.0811	0.6630	0.7481	0.060*
C3	−0.06711 (18)	0.76743 (13)	0.64283 (16)	0.0590 (4)
H3	−0.1597	0.7881	0.6275	0.071*
C4	0.02163 (19)	0.81095 (11)	0.59322 (15)	0.0557 (4)
H4	−0.0108	0.8607	0.5440	0.067*
C5	0.15918 (18)	0.78080 (11)	0.61644 (16)	0.0548 (4)
H5	0.2191	0.8102	0.5822	0.066*
C6	0.20867 (15)	0.70752 (10)	0.68983 (15)	0.0477 (4)
H6	0.3019	0.6878	0.7060	0.057*
C7	0.01095 (18)	0.45745 (13)	0.66936 (16)	0.0588 (4)
H7A	−0.0252	0.4999	0.6060	0.088*
H7B	−0.0454	0.4605	0.7210	0.088*
H7C	0.0068	0.3968	0.6383	0.088*
C8	0.25582 (17)	0.47960 (10)	0.66388 (14)	0.0463 (3)
H8A	0.3467	0.5047	0.7102	0.056*
H8B	0.2175	0.5182	0.5955	0.056*
C9	0.2778 (2)	0.38392 (11)	0.62405 (14)	0.0531 (4)
H9A	0.1862	0.3602	0.5770	0.064*
H9B	0.3364	0.3884	0.5733	0.064*
C10	0.34519 (14)	0.31529 (10)	0.71947 (12)	0.0404 (3)
C11	0.33172 (14)	0.22281 (10)	0.68971 (12)	0.0413 (3)
H11	0.2803	0.2059	0.6134	0.050*
C12	0.39284 (14)	0.15593 (10)	0.77076 (12)	0.0399 (3)
C13	0.47154 (13)	0.18065 (10)	0.88626 (12)	0.0391 (3)
C14	0.48459 (14)	0.27165 (10)	0.91596 (12)	0.0429 (3)
H14	0.5360	0.2887	0.9922	0.051*
C15	0.42196 (14)	0.33848 (10)	0.83345 (13)	0.0437 (3)
H15	0.4319	0.3996	0.8554	0.052*
C16	0.6248 (2)	0.13091 (15)	1.07208 (15)	0.0661 (5)
H16A	0.7043	0.1641	1.0636	0.099*
H16B	0.6576	0.0755	1.1147	0.099*
H16C	0.5771	0.1676	1.1142	0.099*
C17	0.3105 (2)	0.03597 (13)	0.63220 (16)	0.0655 (5)
H17A	0.2136	0.0561	0.6104	0.098*
H17B	0.3130	−0.0294	0.6279	0.098*
H17C	0.3553	0.0619	0.5796	0.098*
N	0.15832 (12)	0.48049 (8)	0.73455 (10)	0.0398 (3)
O1	0.08318 (15)	0.54928 (9)	0.89196 (10)	0.0632 (3)
O2	0.32561 (12)	0.57504 (8)	0.88559 (10)	0.0597 (3)
O3	0.38351 (13)	0.06447 (7)	0.74855 (10)	0.0576 (3)
O4	0.52907 (12)	0.10956 (8)	0.95905 (9)	0.0554 (3)
S	0.17728 (4)	0.56558 (3)	0.82594 (3)	0.04282 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0437 (7)	0.0361 (7)	0.0379 (7)	0.0028 (5)	0.0145 (5)	−0.0021 (5)
C2	0.0480 (8)	0.0537 (9)	0.0563 (9)	0.0072 (7)	0.0267 (7)	0.0050 (7)
C3	0.0517 (9)	0.0619 (10)	0.0654 (10)	0.0210 (8)	0.0212 (8)	0.0074 (9)
C4	0.0664 (10)	0.0433 (9)	0.0581 (9)	0.0135 (7)	0.0207 (8)	0.0087 (7)
C5	0.0618 (10)	0.0416 (8)	0.0678 (11)	−0.0012 (7)	0.0302 (8)	0.0063 (8)
C6	0.0408 (7)	0.0415 (8)	0.0624 (9)	0.0015 (6)	0.0188 (6)	0.0014 (7)
C7	0.0508 (8)	0.0637 (11)	0.0547 (9)	−0.0121 (8)	0.0066 (7)	−0.0042 (8)
C8	0.0567 (8)	0.0405 (8)	0.0447 (8)	0.0030 (6)	0.0202 (7)	0.0036 (6)
C9	0.0715 (10)	0.0485 (9)	0.0413 (8)	0.0107 (8)	0.0209 (7)	−0.0004 (7)
C10	0.0421 (7)	0.0416 (8)	0.0407 (7)	0.0026 (6)	0.0175 (5)	−0.0027 (6)
C11	0.0421 (7)	0.0450 (8)	0.0355 (7)	0.0008 (6)	0.0107 (5)	−0.0069 (6)
C12	0.0386 (6)	0.0399 (7)	0.0404 (7)	0.0005 (5)	0.0115 (5)	−0.0052 (6)
C13	0.0341 (6)	0.0463 (8)	0.0366 (7)	0.0022 (5)	0.0108 (5)	−0.0026 (6)
C14	0.0356 (6)	0.0515 (8)	0.0391 (7)	−0.0031 (6)	0.0083 (5)	−0.0107 (6)
C15	0.0434 (7)	0.0401 (8)	0.0481 (8)	−0.0037 (6)	0.0153 (6)	−0.0093 (6)
C16	0.0598 (10)	0.0829 (13)	0.0438 (8)	0.0087 (9)	0.0000 (7)	0.0054 (9)
C17	0.0789 (12)	0.0467 (9)	0.0563 (10)	0.0028 (8)	0.0009 (9)	−0.0181 (8)
N	0.0436 (6)	0.0363 (6)	0.0381 (6)	−0.0006 (5)	0.0110 (5)	−0.0007 (5)
O1	0.0888 (9)	0.0641 (8)	0.0482 (6)	0.0084 (6)	0.0383 (6)	0.0079 (6)
O2	0.0581 (7)	0.0543 (7)	0.0491 (6)	0.0022 (5)	−0.0080 (5)	−0.0059 (5)
O3	0.0729 (8)	0.0390 (6)	0.0486 (6)	0.0019 (5)	0.0021 (5)	−0.0087 (5)
O4	0.0631 (7)	0.0524 (7)	0.0422 (6)	0.0095 (5)	0.0048 (5)	0.0015 (5)
S	0.0521 (2)	0.0410 (2)	0.03312 (18)	0.00382 (15)	0.01030 (14)	0.00021 (14)

Geometric parameters (Å, º) top

C1—C6	1.383 (2)	C10—C15	1.381 (2)
C1—C2	1.383 (2)	C10—C11	1.397 (2)
C1—S	1.7604 (14)	C11—C12	1.379 (2)
C2—C3	1.382 (2)	C11—H11	0.9300
C2—H2	0.9300	C12—O3	1.3635 (18)
C3—C4	1.369 (3)	C12—C13	1.4062 (18)
C3—H3	0.9300	C13—O4	1.3631 (17)
C4—C5	1.378 (2)	C13—C14	1.375 (2)
C4—H4	0.9300	C14—C15	1.391 (2)
C5—C6	1.377 (2)	C14—H14	0.9300
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—O4	1.4229 (19)
C7—N	1.4638 (19)	C16—H16A	0.9600
C7—H7A	0.9600	C16—H16B	0.9600
C7—H7B	0.9600	C16—H16C	0.9600
C7—H7C	0.9600	C17—O3	1.4173 (19)
C8—N	1.4773 (19)	C17—H17A	0.9600
C8—C9	1.519 (2)	C17—H17B	0.9600
C8—H8A	0.9700	C17—H17C	0.9600
C8—H8B	0.9700	N—S	1.6317 (12)
C9—C10	1.511 (2)	O1—S	1.4254 (13)
C9—H9A	0.9700	O2—S	1.4262 (11)
C9—H9B	0.9700

C6—C1—C2	120.38 (14)	C12—C11—C10	121.59 (13)
C6—C1—S	119.60 (11)	C12—C11—H11	119.2
C2—C1—S	119.92 (12)	C10—C11—H11	119.2
C3—C2—C1	119.37 (15)	O3—C12—C11	124.96 (12)
C3—C2—H2	120.3	O3—C12—C13	115.34 (13)
C1—C2—H2	120.3	C11—C12—C13	119.70 (13)
C4—C3—C2	120.51 (15)	O4—C13—C14	126.05 (12)
C4—C3—H3	119.7	O4—C13—C12	115.10 (12)
C2—C3—H3	119.7	C14—C13—C12	118.85 (13)
C3—C4—C5	119.85 (15)	C13—C14—C15	120.89 (13)
C3—C4—H4	120.1	C13—C14—H14	119.6
C5—C4—H4	120.1	C15—C14—H14	119.6
C6—C5—C4	120.59 (16)	C10—C15—C14	120.93 (14)
C6—C5—H5	119.7	C10—C15—H15	119.5
C4—C5—H5	119.7	C14—C15—H15	119.5
C5—C6—C1	119.30 (14)	O4—C16—H16A	109.5
C5—C6—H6	120.4	O4—C16—H16B	109.5
C1—C6—H6	120.4	H16A—C16—H16B	109.5
N—C7—H7A	109.5	O4—C16—H16C	109.5
N—C7—H7B	109.5	H16A—C16—H16C	109.5
H7A—C7—H7B	109.5	H16B—C16—H16C	109.5
N—C7—H7C	109.5	O3—C17—H17A	109.5
H7A—C7—H7C	109.5	O3—C17—H17B	109.5
H7B—C7—H7C	109.5	H17A—C17—H17B	109.5
N—C8—C9	112.04 (13)	O3—C17—H17C	109.5
N—C8—H8A	109.2	H17A—C17—H17C	109.5
C9—C8—H8A	109.2	H17B—C17—H17C	109.5
N—C8—H8B	109.2	C7—N—C8	114.72 (12)
C9—C8—H8B	109.2	C7—N—S	114.70 (11)
H8A—C8—H8B	107.9	C8—N—S	115.88 (9)
C10—C9—C8	116.64 (13)	C12—O3—C17	117.65 (13)
C10—C9—H9A	108.1	C13—O4—C16	117.44 (13)
C8—C9—H9A	108.1	O2—S—O1	119.54 (8)
C10—C9—H9B	108.1	O2—S—N	106.98 (7)
C8—C9—H9B	108.1	O1—S—N	106.87 (7)
H9A—C9—H9B	107.3	O2—S—C1	108.34 (7)
C15—C10—C11	118.04 (13)	O1—S—C1	108.16 (7)
C15—C10—C9	124.05 (14)	N—S—C1	106.21 (6)
C11—C10—C9	117.90 (13)

C6—C1—C2—C3	−0.6 (2)	C11—C10—C15—C14	0.3 (2)
S—C1—C2—C3	−177.00 (13)	C9—C10—C15—C14	−178.10 (14)
C1—C2—C3—C4	1.0 (3)	C13—C14—C15—C10	−0.1 (2)
C2—C3—C4—C5	−0.5 (3)	C9—C8—N—C7	−67.78 (17)
C3—C4—C5—C6	−0.4 (3)	C9—C8—N—S	154.94 (11)
C4—C5—C6—C1	0.8 (3)	C11—C12—O3—C17	2.8 (2)
C2—C1—C6—C5	−0.2 (2)	C13—C12—O3—C17	−177.37 (15)
S—C1—C6—C5	176.16 (12)	C14—C13—O4—C16	−7.8 (2)
N—C8—C9—C10	−62.34 (19)	C12—C13—O4—C16	171.97 (14)
C8—C9—C10—C15	−18.9 (2)	C7—N—S—O2	176.93 (11)
C8—C9—C10—C11	162.67 (14)	C8—N—S—O2	−45.78 (12)
C15—C10—C11—C12	−0.1 (2)	C7—N—S—O1	47.78 (13)
C9—C10—C11—C12	178.44 (14)	C8—N—S—O1	−174.93 (10)
C10—C11—C12—O3	179.51 (14)	C7—N—S—C1	−67.51 (12)
C10—C11—C12—C13	−0.4 (2)	C8—N—S—C1	69.77 (11)
O3—C12—C13—O4	0.95 (19)	C6—C1—S—O2	32.79 (14)
C11—C12—C13—O4	−179.17 (13)	C2—C1—S—O2	−150.81 (13)
O3—C12—C13—C14	−179.30 (13)	C6—C1—S—O1	163.73 (12)
C11—C12—C13—C14	0.6 (2)	C2—C1—S—O1	−19.87 (15)
O4—C13—C14—C15	179.37 (14)	C6—C1—S—N	−81.85 (13)
C12—C13—C14—C15	−0.3 (2)	C2—C1—S—N	94.55 (13)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the phenyl plane C10–C15.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2ⁱ	0.93	2.60	3.380 (2)	142
C8—H8A···O3ⁱⁱ	0.97	2.71	3.620 (2)	156
C4—H4···O1ⁱⁱⁱ	0.93	2.65	3.369 (2)	135
C3—H3···Cg2^iv	0.93	2.91	3.661 (2)	139
C6—H6···Cg2ⁱⁱ	0.93	3.05	3.827 (8)	123

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₁NO₄S
M_r	335.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.9383 (3), 14.6494 (4), 12.0097 (3)
β (°)	108.535 (1)
V (Å³)	1657.80 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.40 × 0.40 × 0.30

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.879, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	20493, 4353, 3342
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.115, 1.00
No. of reflections	4353
No. of parameters	212
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.30

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the phenyl plane C10–C15.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2ⁱ	0.93	2.60	3.380 (2)	142.2
C8—H8A···O3ⁱⁱ	0.97	2.71	3.620 (2)	156.0
C4—H4···O1ⁱⁱⁱ	0.93	2.65	3.369 (2)	134.5
C3—H3···Cg2^iv	0.93	2.91	3.661 (2)	139
C6—H6···Cg2ⁱⁱ	0.93	3.05	3.827 (8)	123

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

Acknowledgements

The authors wish to acknowledge SAIF, IIT-Madras, for the data collection.

References

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Volume 68| Part 3| March 2012| Page o882

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