N-[2-(3,4-Dimeth­oxy­phenyl)eth­yl]-N-methyl­naphthalene-1-sulfonamide

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

doi:10.1107/S1600536812008203

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o890

doi:10.1107/S1600536812008203

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N-[2-(3,4-Dimethoxyphenyl)ethyl]-N-methylnaphthalene-1-sulfonamide

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 February 2012; accepted 23 February 2012; online 29 February 2012)

In the title compound, C₂₁H₂₃NO₄S, the dihedral angle between the naphthalene residue and the benzene ring is 7.66 (3)°. In the molecule, there are some short C—H⋯O interactions. In the crystal, the structure is stabilized by weak intramolecular C—H⋯O hydrogen bonds and the crystal structure is stabilized by weak C—H⋯O, C—H⋯π and π–π [centroid–centroid distance = 3.710 (2) Å] interactions.

Related literature

For biological activities of sulfonamide derivatives, see: Schultz et al. (2001 ); Sheppard (2006 ); Xiong et al. (2007 ). For related structures, see: Vennila, Thilagavathi et al. (2008 ); Vennila, Kavitha et al. (2008 ).

Experimental

Crystal data

C₂₁H₂₃NO₄S
M_r = 385.46
Orthorhombic, P b c a
a = 10.070 (5) Å
b = 14.120 (4) Å
c = 27.229 (5) Å
V = 3872 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 295 K
0.34 × 0.30 × 0.28 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.937, T_max = 0.948
9215 measured reflections
5239 independent reflections
3248 reflections with I > 2σ(I)
R_int = 0.041
Standard reflections: 0

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.120
S = 1.01
5239 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C2–C7 and C14–C19 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2	0.93	2.53	3.132 (3)	122
C10—H10⋯O1	0.93	2.37	2.804 (3)	109
C11—H11B⋯O2	0.96	2.34	2.821 (3)	110
C4—H4⋯O3ⁱ	0.93	2.46	3.310 (3)	152
C8—H8⋯Cg3ⁱⁱ	0.93	2.59	3.488 (3)	163
C20—H20C⋯Cg2ⁱⁱⁱ	0.96	2.92	3.740 (3)	144
Symmetry codes: (i) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536812008203/bt5826sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008203/bt5826Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812008203/bt5826Isup3.cml

checkCIF report

Comment top

In view of the biological activities of sulfonamide derivatives such as insecticidal, antimicrobial and anticancer (Schultz et al., 2001; Sheppard et al., 2006; Xiong et al., 2007), we herewith report the crystal structure of the title compound (I), (Fig. 1). The geometric parameters of the title compound (I) are comparable with the similar reported compounds (Vennila, Thilagavathi et al., 2008; Vennila, Kavitha et al., 2008).

The naphthalene and benzene rings are oriented at an angle of 7.66 (3)°. The molecular structure is stabilized by weak intramolecular C-H···O hydrogen bonds (Table 1) and the crystal structure is formed by weak intermolecular C-H···O (Fig. 2), C-H..π (Table 1) and π–π [Cg1···Cg3 (x,1/2-y,1/2+z) distance 3.710 (2)Å; Cg1 and Cg3 are the centroids of the rings (C1/C2/C7/C8/C9/C10) and (C14-C19), respectively] interactions.

Related literature top

For biological activities of sulfonamide derivatives, see: Schultz et al. (2001); Sheppard (2006); Xiong et al. (2007). For related structures, see: Vennila, Thilagavathi et al. (2008); Vennila, Kavitha et al. (2008).

Experimental top

About 5.0 g (25 mmol) of [2-(3, 4-dimethoxy-phenyl)-ethyl]-methyl-amine and 6.8 g (30 mmol) of naphthalene-1-sulfonyl chloride were dissolved in 40mL of methylene dichloride. To this mixture, 5.1 g (51 mmol) of triethylamine was added at 298 K. The reaction mixture was warmed to 313 K and maintained at that temperature for 4 to 6 hrs. The completion of the reaction was checked by TLC. The reaction mixture was cooled to 288 K and added 50 mL of water. The organic layer was separated, washed to neutral pH with 5 % aqueous sodium bicarbonate solution, dried over anhydrous sodium sulphate and concentrated. The crude compound was column purified by using petroleum ether and ethyl acetate. Recrystallisation of the compound with the mixture of ethyl acetate and n-heptane mixture yielded colourless crystals of diffraction quality.

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. Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

N-[2-(3,4-Dimethoxyphenyl)ethyl]-N-methylnaphthalene-1-sulfonamide top

Crystal data top

C₂₁H₂₃NO₄S	F(000) = 1632
M_r = 385.46	D_x = 1.323 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 26403 reflections
a = 10.070 (5) Å	θ = 2.5–29.3°
b = 14.120 (4) Å	µ = 0.19 mm⁻¹
c = 27.229 (5) Å	T = 295 K
V = 3872 (2) Å³	Block, colourless
Z = 8	0.34 × 0.30 × 0.28 mm

Data collection top

Bruker Kappa APEXII diffractometer	5239 independent reflections
Radiation source: fine-focus sealed tube	3248 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω and ϕ scans	θ_max = 29.3°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.937, T_max = 0.948	k = −10→19
9215 measured reflections	l = −36→37

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0441P)² + 1.1352P] where P = (F_o² + 2F_c²)/3
5239 reflections	(Δ/σ)_max < 0.001
247 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₁H₂₃NO₄S	V = 3872 (2) Å³
M_r = 385.46	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.070 (5) Å	µ = 0.19 mm⁻¹
b = 14.120 (4) Å	T = 295 K
c = 27.229 (5) Å	0.34 × 0.30 × 0.28 mm

Data collection top

Bruker Kappa APEXII diffractometer	5239 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3248 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.948	R_int = 0.041
9215 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.01	Δρ_max = 0.21 e Å⁻³
5239 reflections	Δρ_min = −0.38 e Å⁻³
247 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.92055 (17)	0.36733 (11)	0.08433 (6)	0.0419 (4)
C2	0.94855 (17)	0.35623 (11)	0.13542 (6)	0.0404 (4)
C3	0.8706 (2)	0.30395 (13)	0.16901 (7)	0.0524 (5)
H3	0.7930	0.2749	0.1583	0.063*
C4	0.9080 (2)	0.29561 (14)	0.21685 (7)	0.0623 (6)
H4	0.8551	0.2612	0.2384	0.075*
C5	1.0239 (2)	0.33759 (14)	0.23403 (7)	0.0640 (6)
H5	1.0485	0.3303	0.2667	0.077*
C6	1.1009 (2)	0.38904 (14)	0.20327 (7)	0.0583 (5)
H6	1.1779	0.4173	0.2151	0.070*
C7	1.06558 (19)	0.40032 (12)	0.15342 (6)	0.0463 (4)
C8	1.1458 (2)	0.45408 (13)	0.12135 (8)	0.0586 (5)
H8	1.2222	0.4829	0.1334	0.070*
C9	1.1141 (2)	0.46457 (14)	0.07347 (8)	0.0614 (5)
H9	1.1674	0.5012	0.0531	0.074*
C10	1.0010 (2)	0.42025 (12)	0.05468 (7)	0.0521 (5)
H10	0.9803	0.4268	0.0216	0.063*
C11	0.6973 (2)	0.13869 (18)	0.06506 (9)	0.0765 (7)
H11A	0.6656	0.1242	0.0327	0.115*
H11B	0.6282	0.1695	0.0834	0.115*
H11C	0.7224	0.0812	0.0814	0.115*
C12	0.92293 (19)	0.16608 (13)	0.03129 (6)	0.0498 (4)
H12A	0.9896	0.2153	0.0282	0.060*
H12B	0.8901	0.1516	−0.0014	0.060*
C13	0.98652 (19)	0.07800 (12)	0.05306 (6)	0.0493 (4)
H13A	0.9214	0.0274	0.0533	0.059*
H13B	1.0591	0.0583	0.0320	0.059*
C14	1.03892 (17)	0.09117 (11)	0.10439 (6)	0.0408 (4)
C15	0.98454 (18)	0.04479 (12)	0.14386 (6)	0.0481 (4)
H15	0.9130	0.0042	0.1390	0.058*
C16	1.03471 (19)	0.05758 (12)	0.19086 (6)	0.0496 (4)
H16	0.9955	0.0264	0.2172	0.059*
C17	1.14125 (18)	0.11561 (12)	0.19879 (6)	0.0432 (4)
C18	1.19942 (16)	0.16272 (12)	0.15871 (6)	0.0400 (4)
C19	1.14727 (16)	0.15094 (12)	0.11246 (6)	0.0396 (4)
H19	1.1847	0.1833	0.0861	0.048*
C20	1.1405 (3)	0.08946 (18)	0.28507 (7)	0.0775 (7)
H20A	1.0503	0.1109	0.2878	0.116*
H20B	1.1889	0.1075	0.3140	0.116*
H20C	1.1417	0.0218	0.2818	0.116*
C21	1.3788 (2)	0.25648 (17)	0.12955 (8)	0.0718 (6)
H21A	1.4030	0.2076	0.1068	0.108*
H21B	1.4575	0.2871	0.1415	0.108*
H21C	1.3233	0.3021	0.1133	0.108*
N1	0.81255 (14)	0.20151 (10)	0.06160 (5)	0.0460 (4)
O1	0.78111 (16)	0.34316 (12)	0.00575 (6)	0.0787 (5)
O2	0.66402 (14)	0.33351 (11)	0.08444 (7)	0.0782 (5)
O3	1.20031 (14)	0.13109 (10)	0.24318 (4)	0.0611 (4)
O4	1.30859 (13)	0.21602 (10)	0.16952 (5)	0.0563 (3)
S1	0.78111 (5)	0.31428 (4)	0.056242 (19)	0.05377 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0431 (9)	0.0320 (8)	0.0507 (10)	0.0023 (7)	0.0041 (8)	0.0032 (7)
C2	0.0467 (9)	0.0276 (8)	0.0469 (9)	0.0013 (7)	0.0096 (8)	−0.0001 (7)
C3	0.0557 (11)	0.0467 (11)	0.0549 (11)	−0.0065 (9)	0.0141 (9)	0.0008 (8)
C4	0.0846 (15)	0.0499 (12)	0.0524 (12)	−0.0034 (11)	0.0223 (11)	0.0054 (9)
C5	0.0966 (17)	0.0504 (12)	0.0449 (10)	0.0050 (12)	0.0016 (11)	−0.0040 (9)
C6	0.0765 (14)	0.0458 (11)	0.0526 (11)	−0.0035 (10)	−0.0043 (10)	−0.0114 (9)
C7	0.0569 (11)	0.0311 (9)	0.0510 (10)	−0.0020 (8)	0.0051 (8)	−0.0066 (7)
C8	0.0617 (12)	0.0451 (11)	0.0689 (13)	−0.0199 (9)	0.0048 (10)	−0.0040 (9)
C9	0.0691 (13)	0.0511 (12)	0.0640 (12)	−0.0204 (10)	0.0132 (11)	0.0092 (10)
C10	0.0632 (12)	0.0449 (10)	0.0484 (10)	−0.0020 (9)	0.0045 (9)	0.0100 (8)
C11	0.0538 (13)	0.0750 (16)	0.1008 (18)	−0.0260 (11)	−0.0027 (12)	−0.0060 (13)
C12	0.0542 (11)	0.0564 (11)	0.0389 (9)	−0.0039 (9)	−0.0016 (8)	−0.0026 (8)
C13	0.0562 (11)	0.0451 (10)	0.0467 (10)	−0.0019 (9)	−0.0007 (8)	−0.0122 (8)
C14	0.0465 (9)	0.0346 (8)	0.0413 (9)	0.0060 (7)	0.0008 (7)	−0.0070 (7)
C15	0.0513 (10)	0.0409 (9)	0.0521 (10)	−0.0090 (8)	−0.0017 (9)	−0.0022 (8)
C16	0.0579 (11)	0.0460 (10)	0.0447 (10)	−0.0100 (9)	0.0034 (8)	0.0051 (8)
C17	0.0489 (10)	0.0420 (9)	0.0388 (9)	−0.0004 (8)	−0.0017 (8)	−0.0016 (7)
C18	0.0384 (9)	0.0369 (9)	0.0447 (9)	0.0000 (7)	0.0020 (7)	−0.0030 (7)
C19	0.0416 (9)	0.0367 (9)	0.0405 (9)	0.0037 (7)	0.0068 (7)	−0.0008 (7)
C20	0.1034 (19)	0.0884 (16)	0.0407 (11)	−0.0257 (15)	−0.0018 (12)	0.0064 (11)
C21	0.0554 (12)	0.0881 (17)	0.0717 (14)	−0.0249 (12)	0.0095 (11)	0.0059 (12)
N1	0.0383 (7)	0.0474 (9)	0.0524 (9)	−0.0076 (6)	−0.0042 (6)	0.0007 (7)
O1	0.0816 (11)	0.0849 (11)	0.0697 (10)	−0.0032 (9)	−0.0314 (8)	0.0276 (8)
O2	0.0397 (8)	0.0758 (11)	0.1191 (14)	0.0113 (7)	0.0055 (8)	0.0047 (9)
O3	0.0721 (9)	0.0705 (9)	0.0408 (7)	−0.0192 (7)	−0.0081 (6)	0.0050 (6)
O4	0.0484 (7)	0.0687 (9)	0.0518 (7)	−0.0179 (6)	−0.0003 (6)	0.0008 (6)
S1	0.0413 (2)	0.0552 (3)	0.0648 (3)	0.0029 (2)	−0.0096 (2)	0.0108 (2)

Geometric parameters (Å, º) top

C1—C10	1.366 (2)	C12—H12B	0.9700
C1—C2	1.428 (2)	C13—C14	1.506 (2)
C1—S1	1.7656 (19)	C13—H13A	0.9700
C2—C3	1.413 (2)	C13—H13B	0.9700
C2—C7	1.420 (2)	C14—C15	1.372 (2)
C3—C4	1.361 (3)	C14—C19	1.397 (2)
C3—H3	0.9300	C15—C16	1.388 (2)
C4—C5	1.390 (3)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.367 (2)
C5—C6	1.353 (3)	C16—H16	0.9300
C5—H5	0.9300	C17—O3	1.365 (2)
C6—C7	1.412 (3)	C17—C18	1.406 (2)
C6—H6	0.9300	C18—O4	1.364 (2)
C7—C8	1.411 (3)	C18—C19	1.375 (2)
C8—C9	1.350 (3)	C19—H19	0.9300
C8—H8	0.9300	C20—O3	1.418 (2)
C9—C10	1.396 (3)	C20—H20A	0.9600
C9—H9	0.9300	C20—H20B	0.9600
C10—H10	0.9300	C20—H20C	0.9600
C11—N1	1.464 (2)	C21—O4	1.418 (2)
C11—H11A	0.9600	C21—H21A	0.9600
C11—H11B	0.9600	C21—H21B	0.9600
C11—H11C	0.9600	C21—H21C	0.9600
C12—N1	1.472 (2)	N1—S1	1.6300 (16)
C12—C13	1.519 (2)	O1—S1	1.4341 (15)
C12—H12A	0.9700	O2—S1	1.4330 (16)

C10—C1—C2	121.23 (16)	C14—C13—H13B	108.7
C10—C1—S1	116.60 (14)	C12—C13—H13B	108.7
C2—C1—S1	122.17 (12)	H13A—C13—H13B	107.6
C3—C2—C7	117.79 (17)	C15—C14—C19	118.48 (16)
C3—C2—C1	125.33 (17)	C15—C14—C13	121.88 (16)
C7—C2—C1	116.87 (15)	C19—C14—C13	119.63 (15)
C4—C3—C2	120.74 (19)	C14—C15—C16	120.98 (17)
C4—C3—H3	119.6	C14—C15—H15	119.5
C2—C3—H3	119.6	C16—C15—H15	119.5
C3—C4—C5	121.16 (19)	C17—C16—C15	120.63 (16)
C3—C4—H4	119.4	C17—C16—H16	119.7
C5—C4—H4	119.4	C15—C16—H16	119.7
C6—C5—C4	120.11 (19)	O3—C17—C16	125.31 (16)
C6—C5—H5	119.9	O3—C17—C18	115.48 (16)
C4—C5—H5	119.9	C16—C17—C18	119.20 (16)
C5—C6—C7	120.8 (2)	O4—C18—C19	124.91 (15)
C5—C6—H6	119.6	O4—C18—C17	115.41 (15)
C7—C6—H6	119.6	C19—C18—C17	119.66 (16)
C8—C7—C6	120.76 (18)	C18—C19—C14	121.04 (15)
C8—C7—C2	119.83 (17)	C18—C19—H19	119.5
C6—C7—C2	119.41 (17)	C14—C19—H19	119.5
C9—C8—C7	121.38 (19)	O3—C20—H20A	109.5
C9—C8—H8	119.3	O3—C20—H20B	109.5
C7—C8—H8	119.3	H20A—C20—H20B	109.5
C8—C9—C10	119.84 (18)	O3—C20—H20C	109.5
C8—C9—H9	120.1	H20A—C20—H20C	109.5
C10—C9—H9	120.1	H20B—C20—H20C	109.5
C1—C10—C9	120.81 (18)	O4—C21—H21A	109.5
C1—C10—H10	119.6	O4—C21—H21B	109.5
C9—C10—H10	119.6	H21A—C21—H21B	109.5
N1—C11—H11A	109.5	O4—C21—H21C	109.5
N1—C11—H11B	109.5	H21A—C21—H21C	109.5
H11A—C11—H11B	109.5	H21B—C21—H21C	109.5
N1—C11—H11C	109.5	C11—N1—C12	115.39 (16)
H11A—C11—H11C	109.5	C11—N1—S1	116.34 (14)
H11B—C11—H11C	109.5	C12—N1—S1	115.37 (12)
N1—C12—C13	112.19 (14)	C17—O3—C20	117.45 (16)
N1—C12—H12A	109.2	C18—O4—C21	117.28 (15)
C13—C12—H12A	109.2	O2—S1—O1	117.38 (10)
N1—C12—H12B	109.2	O2—S1—N1	107.27 (9)
C13—C12—H12B	109.2	O1—S1—N1	111.32 (9)
H12A—C12—H12B	107.9	O2—S1—C1	109.99 (10)
C14—C13—C12	114.14 (14)	O1—S1—C1	107.14 (9)
C14—C13—H13A	108.7	N1—S1—C1	102.78 (8)
C12—C13—H13A	108.7

C10—C1—C2—C3	179.26 (17)	C15—C16—C17—C18	0.3 (3)
S1—C1—C2—C3	−0.5 (2)	O3—C17—C18—O4	1.2 (2)
C10—C1—C2—C7	−1.8 (2)	C16—C17—C18—O4	−177.34 (16)
S1—C1—C2—C7	178.39 (12)	O3—C17—C18—C19	179.58 (15)
C7—C2—C3—C4	−0.7 (3)	C16—C17—C18—C19	1.0 (3)
C1—C2—C3—C4	178.20 (17)	O4—C18—C19—C14	176.77 (15)
C2—C3—C4—C5	−0.4 (3)	C17—C18—C19—C14	−1.4 (2)
C3—C4—C5—C6	1.0 (3)	C15—C14—C19—C18	0.5 (2)
C4—C5—C6—C7	−0.5 (3)	C13—C14—C19—C18	−178.45 (15)
C5—C6—C7—C8	179.94 (19)	C13—C12—N1—C11	−65.3 (2)
C5—C6—C7—C2	−0.6 (3)	C13—C12—N1—S1	154.41 (12)
C3—C2—C7—C8	−179.36 (17)	C16—C17—O3—C20	−5.1 (3)
C1—C2—C7—C8	1.6 (2)	C18—C17—O3—C20	176.43 (18)
C3—C2—C7—C6	1.2 (2)	C19—C18—O4—C21	−4.9 (3)
C1—C2—C7—C6	−177.81 (16)	C17—C18—O4—C21	173.40 (17)
C6—C7—C8—C9	179.26 (19)	C11—N1—S1—O2	34.67 (17)
C2—C7—C8—C9	−0.2 (3)	C12—N1—S1—O2	174.52 (13)
C7—C8—C9—C10	−1.2 (3)	C11—N1—S1—O1	−95.00 (16)
C2—C1—C10—C9	0.5 (3)	C12—N1—S1—O1	44.86 (15)
S1—C1—C10—C9	−179.67 (15)	C11—N1—S1—C1	150.62 (15)
C8—C9—C10—C1	1.0 (3)	C12—N1—S1—C1	−69.52 (14)
N1—C12—C13—C14	−57.6 (2)	C10—C1—S1—O2	−130.70 (15)
C12—C13—C14—C15	113.75 (19)	C2—C1—S1—O2	49.10 (16)
C12—C13—C14—C19	−67.3 (2)	C10—C1—S1—O1	−2.07 (17)
C19—C14—C15—C16	0.7 (3)	C2—C1—S1—O1	177.73 (14)
C13—C14—C15—C16	179.70 (16)	C10—C1—S1—N1	115.32 (14)
C14—C15—C16—C17	−1.1 (3)	C2—C1—S1—N1	−64.88 (15)
C15—C16—C17—O3	−178.17 (17)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C2–C7 and C14–C19 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2	0.93	2.53	3.132 (3)	122
C10—H10···O1	0.93	2.37	2.804 (3)	109
C11—H11B···O2	0.96	2.34	2.821 (3)	110
C4—H4···O3ⁱ	0.93	2.46	3.310 (3)	152
C8—H8···Cg3ⁱⁱ	0.93	2.59	3.488 (3)	163
C20—H20C···Cg2ⁱⁱⁱ	0.96	2.92	3.740 (3)	144

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₃NO₄S
M_r	385.46
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	10.070 (5), 14.120 (4), 27.229 (5)
V (Å³)	3872 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.34 × 0.30 × 0.28

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.937, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	9215, 5239, 3248
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.689

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.120, 1.01
No. of reflections	5239
No. of parameters	247
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.38

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

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C2–C7 and C14–C19 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2	0.93	2.53	3.132 (3)	122
C10—H10···O1	0.93	2.37	2.804 (3)	109
C11—H11B···O2	0.96	2.34	2.821 (3)	110
C4—H4···O3ⁱ	0.93	2.46	3.310 (3)	152
C8—H8···Cg3ⁱⁱ	0.93	2.59	3.488 (3)	163
C20—H20C···Cg2ⁱⁱⁱ	0.96	2.92	3.740 (3)	144

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

Acknowledgements

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

References

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