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

Vennila, J.P.; Thiruvadigal, D.J.; Kavitha, H.P.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536811029746

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2186

doi:10.1107/S1600536811029746

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

Jasmine P. Vennila,^a D. John Thiruvadigal,^b Helen P. Kavitha,^c G. Chakkaravarthi ^d ^* and V. Manivannan ^e

^aDepartment of Physics, Panimalar Institute of Technology, Chennai 602 103, India, ^bDepartment of Physics, SRM University, Kattankulathur Campus, Chennai, India, ^cDepartment of Chemistry, SRM University, Ramapuram Campus, Chennai 600 089, India, ^dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com

(Received 21 July 2011; accepted 22 July 2011; online 30 July 2011)

In the title compound, C₁₈H₂₃NO₄S, the dihedral angle between the two aromatic rings is 29.14 (7)°. The S atom has a distorted tetrahedral geometry [106.15 (9)–119.54 (10)°]. The crystal structure exhibits weak C—H⋯O and π–π interactions.

Related literature

For the biological activity of sulfonamide derivatives, see: Chumakov et al. (2006 ); Kremer et al. (2006 ). For related structures, see: Khan et al. (2010 ); Sharif et al. (2010 ).

Experimental

Crystal data

C₁₈H₂₃NO₄S
M_r = 349.43
Monoclinic, P 2₁ /n
a = 5.7814 (4) Å
b = 13.9861 (12) Å
c = 21.9791 (18) Å
β = 92.949 (4)°
V = 1774.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 295 K
0.30 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.942, T_max = 0.960
18724 measured reflections
3343 independent reflections
2614 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.110
S = 1.04
3343 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.93	2.54	3.452 (2)	166
C18—H18B⋯O2ⁱⁱ	0.96	2.38	3.302 (3)	160
Symmetry codes: (i) x-1, y, z; (ii) $[x-{\script{3\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811029746/bt5588sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029746/bt5588Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811029746/bt5588Isup3.cml

checkCIF report

Comment top

Sulfonamide derivatives are extensively used in medicine as they possess a wide range of medicinal, pharmacological and antimicrobial properties (Chumakov et al., 2006, Kremer et al., 2006). We report the crystal structure of the titled compound (I) (Fig. 1).

In the title compound (I), the geometric pararameters are similar with the reported similar structures (Khan et al., 2010; Sharif et al., 2010). The S atom of the title molecule has a distorted tetrahedral geometry, with S1—O1 = 1.4210 (15), S1—O2 = 1.4195 (15), S1—N1 = 1.6391 (17), S1—C1 = 1.7538 (19) Å, O1—S1—O2 = 119.54 (10), O1—S1—N1 = 106.83 (9), O1—S1—C7 = 108.64 (9), O2—S1—N1 = 106.32 (9), O2—S1—C7 = 108.57 (9) and N1—S1—C7 = 106.15 (9)°.

The dihedral angle between the two rings C1—C6 and C11—C16 is 29.14 (7)°. The crystal structure exhibits weak C—H···O (Fig.2 and Table 1) and π–π [Cg1···Cg2 (-x,2 - y,-z) distance of 5.2909 (13)Å and Cg2···Cg2 (-x,1 - y,-z) distance of 4.7146 (12) Å; Cg1 and Cg2 are the centroids of the rings C1—C6 and C11—C16, respectively] interactions.

Related literature top

For the biological activity of sulfonamide derivatives, see: Chumakov et al. (2006); Kremer et al. (2006). For related structures, see: Khan et al. (2010); Sharif et al. (2010).

Experimental top

2-(3,4-dimethoxyphenyl)-N-methyl ethanamine (51 mmol) was dissolved in dichloromethane (20 ml) in a round bottom flask. To this, added triethylamine (10.2 mmol) with stirring for 5 minutes. Then 4-methylbenzene-1-sulfonyl chloride (51 mmol) was added into the reaction mass and heated to 50 °C for 6 hrs. After cooling the reaction mixture to the normal 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 the diffraction quality crystals.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the a axis. H-bonds are shown as dashed lines; H atoms not involved in hydrogen bonding have been omitted.

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

Crystal data top

C₁₈H₂₃NO₄S	F(000) = 744
M_r = 349.43	D_x = 1.308 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6145 reflections
a = 5.7814 (4) Å	θ = 2.4–25.5°
b = 13.9861 (12) Å	µ = 0.20 mm⁻¹
c = 21.9791 (18) Å	T = 295 K
β = 92.949 (4)°	Block, colourless
V = 1774.9 (2) Å³	0.30 × 0.24 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	3343 independent reflections
Radiation source: fine-focus sealed tube	2614 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω and ϕ scans	θ_max = 25.8°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→7
T_min = 0.942, T_max = 0.960	k = −16→17
18724 measured reflections	l = −26→26

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-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0471P)² + 0.6472P] where P = (F_o² + 2F_c²)/3
3343 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₈H₂₃NO₄S	V = 1774.9 (2) Å³
M_r = 349.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.7814 (4) Å	µ = 0.20 mm⁻¹
b = 13.9861 (12) Å	T = 295 K
c = 21.9791 (18) Å	0.30 × 0.24 × 0.20 mm
β = 92.949 (4)°

Data collection top

Bruker Kappa APEXII diffractometer	3343 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2614 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.960	R_int = 0.036
18724 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.04	Δρ_max = 0.19 e Å⁻³
3343 reflections	Δρ_min = −0.30 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.

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

	x	y	z	U_iso*/U_eq
S1	0.58829 (8)	0.85799 (4)	0.11159 (2)	0.04660 (17)
O1	0.6833 (3)	0.87108 (11)	0.05383 (7)	0.0609 (4)
O2	0.7388 (3)	0.84655 (12)	0.16418 (7)	0.0663 (5)
O3	0.0375 (3)	0.48564 (11)	−0.16121 (7)	0.0607 (4)
O4	−0.3215 (2)	0.58964 (12)	−0.18094 (6)	0.0612 (4)
N1	0.4284 (3)	0.76123 (11)	0.10662 (7)	0.0430 (4)
C1	0.3980 (3)	0.95272 (13)	0.12431 (8)	0.0425 (4)
C2	0.3502 (4)	0.97724 (15)	0.18308 (9)	0.0537 (5)
H2	0.4308	0.9487	0.2160	0.064*
C3	0.1823 (4)	1.04423 (16)	0.19236 (11)	0.0628 (6)
H3	0.1501	1.0610	0.2320	0.075*
C4	0.0602 (4)	1.08733 (15)	0.14425 (11)	0.0597 (6)
C5	0.1148 (4)	1.06328 (16)	0.08611 (11)	0.0615 (6)
H5	0.0368	1.0929	0.0532	0.074*
C6	0.2822 (4)	0.99631 (15)	0.07548 (9)	0.0522 (5)
H6	0.3167	0.9807	0.0358	0.063*
C7	−0.1298 (5)	1.15787 (19)	0.15501 (15)	0.0872 (9)
H7A	−0.0652	1.2209	0.1591	0.131*
H7B	−0.2038	1.1412	0.1916	0.131*
H7C	−0.2416	1.1565	0.1212	0.131*
C8	0.3156 (4)	0.73564 (17)	0.16243 (10)	0.0587 (6)
H8A	0.1778	0.7732	0.1656	0.088*
H8B	0.4194	0.7478	0.1971	0.088*
H8C	0.2755	0.6690	0.1613	0.088*
C9	0.2771 (4)	0.75162 (14)	0.05110 (9)	0.0492 (5)
H9A	0.3440	0.7863	0.0181	0.059*
H9B	0.1272	0.7796	0.0580	0.059*
C10	0.2458 (4)	0.64822 (14)	0.03316 (9)	0.0497 (5)
H10A	0.3961	0.6211	0.0256	0.060*
H10B	0.1841	0.6135	0.0669	0.060*
C11	0.0868 (3)	0.63423 (13)	−0.02258 (8)	0.0408 (4)
C12	−0.1148 (3)	0.68548 (15)	−0.03237 (9)	0.0489 (5)
H12	−0.1572	0.7298	−0.0034	0.059*
C13	−0.2558 (3)	0.67224 (15)	−0.08459 (9)	0.0498 (5)
H13	−0.3904	0.7082	−0.0905	0.060*
C14	−0.1991 (3)	0.60677 (14)	−0.12757 (8)	0.0420 (4)
C15	0.0004 (3)	0.55133 (13)	−0.11718 (8)	0.0416 (4)
C16	0.1404 (3)	0.56603 (13)	−0.06575 (9)	0.0431 (5)
H16	0.2742	0.5296	−0.0596	0.052*
C17	0.2289 (4)	0.42275 (18)	−0.15152 (13)	0.0742 (7)
H17A	0.3703	0.4588	−0.1508	0.111*
H17B	0.2287	0.3767	−0.1839	0.111*
H17C	0.2169	0.3903	−0.1133	0.111*
C18	−0.4992 (4)	0.65515 (19)	−0.19872 (11)	0.0662 (7)
H18A	−0.6191	0.6526	−0.1701	0.099*
H18B	−0.5626	0.6386	−0.2386	0.099*
H18C	−0.4363	0.7186	−0.1995	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0386 (3)	0.0522 (3)	0.0483 (3)	0.0061 (2)	−0.0042 (2)	−0.0112 (2)
O1	0.0549 (9)	0.0663 (10)	0.0630 (10)	0.0020 (7)	0.0177 (7)	−0.0123 (8)
O2	0.0512 (8)	0.0763 (11)	0.0685 (10)	0.0111 (8)	−0.0249 (7)	−0.0178 (8)
O3	0.0600 (9)	0.0594 (9)	0.0614 (9)	0.0207 (7)	−0.0094 (7)	−0.0241 (7)
O4	0.0541 (8)	0.0736 (11)	0.0538 (9)	0.0195 (7)	−0.0170 (7)	−0.0185 (8)
N1	0.0453 (9)	0.0435 (9)	0.0394 (9)	0.0073 (7)	−0.0075 (7)	−0.0039 (7)
C1	0.0457 (10)	0.0391 (10)	0.0425 (11)	0.0008 (8)	0.0010 (8)	−0.0059 (8)
C2	0.0714 (14)	0.0478 (12)	0.0420 (12)	0.0067 (10)	0.0031 (10)	−0.0046 (9)
C3	0.0869 (17)	0.0490 (13)	0.0548 (14)	0.0079 (12)	0.0246 (12)	−0.0054 (11)
C4	0.0648 (14)	0.0407 (12)	0.0757 (16)	0.0065 (10)	0.0224 (12)	0.0010 (11)
C5	0.0687 (14)	0.0523 (13)	0.0631 (14)	0.0140 (11)	−0.0003 (11)	0.0081 (11)
C6	0.0634 (13)	0.0507 (12)	0.0426 (11)	0.0062 (10)	0.0041 (9)	−0.0023 (9)
C7	0.0838 (18)	0.0608 (16)	0.120 (2)	0.0226 (14)	0.0352 (17)	0.0052 (16)
C8	0.0647 (14)	0.0592 (14)	0.0520 (13)	0.0055 (11)	0.0017 (10)	−0.0009 (11)
C9	0.0508 (11)	0.0448 (11)	0.0501 (12)	0.0040 (9)	−0.0139 (9)	−0.0035 (9)
C10	0.0555 (12)	0.0445 (12)	0.0480 (12)	0.0055 (9)	−0.0088 (9)	−0.0028 (9)
C11	0.0425 (10)	0.0379 (10)	0.0416 (11)	0.0011 (8)	−0.0021 (8)	−0.0006 (8)
C12	0.0471 (11)	0.0535 (12)	0.0459 (11)	0.0088 (9)	0.0014 (9)	−0.0142 (9)
C13	0.0390 (10)	0.0563 (12)	0.0536 (12)	0.0140 (9)	−0.0031 (9)	−0.0107 (10)
C14	0.0378 (9)	0.0457 (11)	0.0420 (11)	0.0025 (8)	−0.0031 (8)	−0.0035 (9)
C15	0.0424 (10)	0.0368 (10)	0.0453 (11)	0.0031 (8)	0.0012 (8)	−0.0068 (8)
C16	0.0407 (10)	0.0354 (10)	0.0525 (12)	0.0076 (8)	−0.0036 (8)	−0.0023 (9)
C17	0.0615 (14)	0.0631 (16)	0.0972 (19)	0.0222 (12)	−0.0040 (13)	−0.0318 (14)
C18	0.0567 (13)	0.0845 (18)	0.0556 (14)	0.0189 (12)	−0.0147 (11)	−0.0004 (12)

Geometric parameters (Å, º) top

S1—O2	1.4195 (15)	C8—H8A	0.9600
S1—O1	1.4210 (15)	C8—H8B	0.9600
S1—N1	1.6391 (17)	C8—H8C	0.9600
S1—C1	1.7538 (19)	C9—C10	1.507 (3)
O3—C15	1.359 (2)	C9—H9A	0.9700
O3—C17	1.421 (3)	C9—H9B	0.9700
O4—C14	1.360 (2)	C10—C11	1.506 (3)
O4—C18	1.417 (2)	C10—H10A	0.9700
N1—C8	1.463 (3)	C10—H10B	0.9700
N1—C9	1.471 (2)	C11—C12	1.376 (3)
C1—C6	1.378 (3)	C11—C16	1.392 (3)
C1—C2	1.378 (3)	C12—C13	1.386 (3)
C2—C3	1.372 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.367 (3)
C3—C4	1.380 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.399 (3)
C4—C5	1.374 (3)	C15—C16	1.372 (2)
C4—C7	1.504 (3)	C16—H16	0.9300
C5—C6	1.375 (3)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C7—H7A	0.9600	C18—H18A	0.9600
C7—H7B	0.9600	C18—H18B	0.9600
C7—H7C	0.9600	C18—H18C	0.9600

O2—S1—O1	119.54 (10)	N1—C9—H9A	109.4
O2—S1—N1	106.32 (9)	C10—C9—H9A	109.4
O1—S1—N1	106.83 (9)	N1—C9—H9B	109.4
O2—S1—C1	108.57 (9)	C10—C9—H9B	109.4
O1—S1—C1	108.64 (9)	H9A—C9—H9B	108.0
N1—S1—C1	106.15 (9)	C11—C10—C9	113.42 (16)
C15—O3—C17	117.52 (16)	C11—C10—H10A	108.9
C14—O4—C18	117.51 (16)	C9—C10—H10A	108.9
C8—N1—C9	113.66 (16)	C11—C10—H10B	108.9
C8—N1—S1	114.86 (13)	C9—C10—H10B	108.9
C9—N1—S1	116.11 (13)	H10A—C10—H10B	107.7
C6—C1—C2	120.49 (18)	C12—C11—C16	117.84 (17)
C6—C1—S1	119.59 (15)	C12—C11—C10	122.44 (17)
C2—C1—S1	119.67 (15)	C16—C11—C10	119.71 (16)
C3—C2—C1	119.1 (2)	C11—C12—C13	121.17 (18)
C3—C2—H2	120.4	C11—C12—H12	119.4
C1—C2—H2	120.4	C13—C12—H12	119.4
C2—C3—C4	121.5 (2)	C14—C13—C12	120.65 (18)
C2—C3—H3	119.2	C14—C13—H13	119.7
C4—C3—H3	119.2	C12—C13—H13	119.7
C5—C4—C3	118.2 (2)	O4—C14—C13	125.54 (17)
C5—C4—C7	120.8 (2)	O4—C14—C15	115.54 (16)
C3—C4—C7	121.0 (2)	C13—C14—C15	118.91 (17)
C4—C5—C6	121.5 (2)	O3—C15—C16	125.43 (17)
C4—C5—H5	119.3	O3—C15—C14	114.69 (16)
C6—C5—H5	119.3	C16—C15—C14	119.88 (17)
C5—C6—C1	119.15 (19)	C15—C16—C11	121.46 (17)
C5—C6—H6	120.4	C15—C16—H16	119.3
C1—C6—H6	120.4	C11—C16—H16	119.3
C4—C7—H7A	109.5	O3—C17—H17A	109.5
C4—C7—H7B	109.5	O3—C17—H17B	109.5
H7A—C7—H7B	109.5	H17A—C17—H17B	109.5
C4—C7—H7C	109.5	O3—C17—H17C	109.5
H7A—C7—H7C	109.5	H17A—C17—H17C	109.5
H7B—C7—H7C	109.5	H17B—C17—H17C	109.5
N1—C8—H8A	109.5	O4—C18—H18A	109.5
N1—C8—H8B	109.5	O4—C18—H18B	109.5
H8A—C8—H8B	109.5	H18A—C18—H18B	109.5
N1—C8—H8C	109.5	O4—C18—H18C	109.5
H8A—C8—H8C	109.5	H18A—C18—H18C	109.5
H8B—C8—H8C	109.5	H18B—C18—H18C	109.5
N1—C9—C10	111.29 (16)

O2—S1—N1—C8	51.06 (16)	C8—N1—C9—C10	−75.5 (2)
O1—S1—N1—C8	179.76 (14)	S1—N1—C9—C10	147.97 (15)
C1—S1—N1—C8	−64.43 (15)	N1—C9—C10—C11	178.43 (16)
O2—S1—N1—C9	−172.91 (13)	C9—C10—C11—C12	−41.2 (3)
O1—S1—N1—C9	−44.21 (15)	C9—C10—C11—C16	140.1 (2)
C1—S1—N1—C9	71.59 (15)	C16—C11—C12—C13	−2.3 (3)
O2—S1—C1—C6	161.10 (17)	C10—C11—C12—C13	178.9 (2)
O1—S1—C1—C6	29.63 (19)	C11—C12—C13—C14	0.8 (3)
N1—S1—C1—C6	−84.94 (18)	C18—O4—C14—C13	11.4 (3)
O2—S1—C1—C2	−24.6 (2)	C18—O4—C14—C15	−168.70 (19)
O1—S1—C1—C2	−156.06 (17)	C12—C13—C14—O4	−178.3 (2)
N1—S1—C1—C2	89.36 (18)	C12—C13—C14—C15	1.8 (3)
C6—C1—C2—C3	1.4 (3)	C17—O3—C15—C16	4.2 (3)
S1—C1—C2—C3	−172.90 (17)	C17—O3—C15—C14	−176.0 (2)
C1—C2—C3—C4	0.1 (4)	O4—C14—C15—O3	−2.4 (3)
C2—C3—C4—C5	−1.6 (4)	C13—C14—C15—O3	177.47 (19)
C2—C3—C4—C7	177.6 (2)	O4—C14—C15—C16	177.38 (18)
C3—C4—C5—C6	1.7 (4)	C13—C14—C15—C16	−2.7 (3)
C7—C4—C5—C6	−177.6 (2)	O3—C15—C16—C11	−179.08 (18)
C4—C5—C6—C1	−0.2 (3)	C14—C15—C16—C11	1.2 (3)
C2—C1—C6—C5	−1.3 (3)	C12—C11—C16—C15	1.4 (3)
S1—C1—C6—C5	172.95 (17)	C10—C11—C16—C15	−179.82 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.59	2.942 (3)	103
C8—H8B···O2	0.96	2.44	2.895 (3)	109
C9—H9A···O1	0.97	2.39	2.880 (3)	111
C12—H12···O1ⁱ	0.93	2.54	3.452 (2)	166
C18—H18B···O2ⁱⁱ	0.96	2.38	3.302 (3)	160

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₃NO₄S
M_r	349.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	5.7814 (4), 13.9861 (12), 21.9791 (18)
β (°)	92.949 (4)
V (Å³)	1774.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.24 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.942, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	18724, 3343, 2614
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.611

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.110, 1.04
No. of reflections	3343
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.30

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.59	2.942 (3)	103
C8—H8B···O2	0.96	2.44	2.895 (3)	109
C9—H9A···O1	0.97	2.39	2.880 (3)	111
C12—H12···O1ⁱ	0.93	2.54	3.452 (2)	166
C18—H18B···O2ⁱⁱ	0.96	2.38	3.302 (3)	160

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

Acknowledgements

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

References

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