(E)-Methyl 3-(2-methyl-1-phenyl­sulfonyl-1H-indol-3-yl)but-2-enoate

Kavitha, T.; Thenmozhi, M.; Gobi Rajeshwaran, G.; Mohanakrishnan, A.K.; Ponnuswamy, M.N.

doi:10.1107/S1600536809002931

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o431

doi:10.1107/S1600536809002931

Open

access

(E)-Methyl 3-(2-methyl-1-phenylsulfonyl-1H-indol-3-yl)but-2-enoate

T. Kavitha,^a M. Thenmozhi,^a G. Gobi Rajeshwaran,^b A. K. Mohanakrishnan ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 24 December 2008; accepted 23 January 2009; online 31 January 2009)

In the title compound, C₂₀H₁₉NO₄S, the indole ring system is planar [r.m.s. deviation = 0.023 (2) Å]. The sulfonyl-bound phenyl ring is almost perpendicular to the indole ring system [dihedral angle = 86.75 (7)°]. The ester group is almost planar (r.m.s. deviation = 0.030 Å) and is oriented at an angle of 62.53 (5)° with respect to the indole ring system. Molecules are linked into a two-dimensional network parallel to the ab plane by intermolecular C—H⋯O hydrogen bonds.

Related literature

For the biological activities of indole and its derivatives, see: Chandrakantha et al. (1992 ); Rodriguez et al. (1985 ). For related literature For the configuration at the S atom, see: Bassindale (1984 ). For the N atom hybridization, see: Beddoes et al. (1986 ).

Experimental

Crystal data

C₂₀H₁₉NO₄S
M_r = 369.42
Monoclinic, P 2₁ /c
a = 8.9498 (3) Å
b = 8.8427 (2) Å
c = 23.2836 (7) Å
β = 97.085 (1)°
V = 1828.60 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 (2) K
0.25 × 0.20 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.957, T_max = 0.968
23203 measured reflections
5673 independent reflections
3833 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.137
S = 1.01
5673 reflections
239 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.93	2.58	3.391 (2)	146
C13—H13⋯O3ⁱⁱ	0.93	2.50	3.277 (2)	141
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y-1, z.

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: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002931/ci2752sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002931/ci2752Isup2.hkl

checkCIF report

Comment top

Indole and its derivatives have long been known for their chemical and biological activities (Chandrakantha et al., 1992). The indole ring system is present in a number of natural products, many of which are found to possess pharmacological properties like anti-microbial, anti-inflammatory and anti-implantation activities (Rodriguez et al., 1985).

Due to Thorpe–Ignold effect (Bassindale, 1984), bond angles around atom S1 show significant deviation from ideal tetrahedral value, with significant deviations in angles O1—S1—O2 [120.37 (9)°] and N1—S1—C10 [104.96 (6)°]. The indole ring system is essentially planar. The sum of the bond angles around atom N1 (355.9°) indicates sp² hybridization (Beddoes et al., 1986). The sulfonyl bound phenyl ring is oriented almost perpendicular to the indole ring system as can be seen from the dihedral angle of 86.75 (7)°. The ester group attached to the indole ring system adopts an extended conformation which is confirmed by the torsion angles C3—C17—C19—C20 = -177.59 (14)°, C17—C19—C20—O4 = -176.02 (15)° and C19—C20—O4—C21 = -178.62 (15)°.

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into a two-dimensional network parallel to the ab plane (Fig. 2).

Related literature top

For the biological activities of indole and its derivatives, see: Chandrakantha et al. (1992); Rodriguez et al. (1985). For related literature, see: Bassindale (1984); Beddoes et al. (1986).

Experimental top

To a stirred suspension of NaH (29 mg, 1.20 mmol, hexane washed) in THF (5 ml), a solution of vinyl indole (0.23 g, 1 mmol) in THF (5 ml) was added and stirred for 30 min at room temperature. To the reaction mixture, a solution of PhSO₂Cl (0.21 g, 1.20 mmol) was added and stirring was continued for further 6 h. After the indole was consumed (monitored by TLC), the reaction mixture was quenched with cold diluted HCl (25 ml), extracted with ethyl acetate (2 × 10 ml) and dried (Na₂SO₄). Removal of solvent followed by recrystallization (MeOH) afforded yellow crystals of the title compound.

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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 20% probability level.
	Fig. 2. Crystal packing of the title compound, viewed down the a axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

(E)-Methyl 3-(2-methyl-1-phenylsulfonyl-1H-indol-3-yl)but-2-enoate top

Crystal data top

C₂₀H₁₉NO₄S	F(000) = 776
M_r = 369.42	D_x = 1.342 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5673 reflections
a = 8.9498 (3) Å	θ = 2.3–31.0°
b = 8.8427 (2) Å	µ = 0.20 mm⁻¹
c = 23.2836 (7) Å	T = 293 K
β = 97.085 (1)°	Block, yellow
V = 1828.60 (9) Å³	0.25 × 0.20 × 0.16 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	5673 independent reflections
Radiation source: fine-focus sealed tube	3833 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and ϕ scans	θ_max = 31.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −12→11
T_min = 0.957, T_max = 0.968	k = −7→12
23203 measured reflections	l = −32→33

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)] = 0.046	H-atom parameters constrained
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.0625P)² + 0.402P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.016
5673 reflections	Δρ_max = 0.30 e Å⁻³
239 parameters	Δρ_min = −0.29 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: 0.0057 (11)

Crystal data top

C₂₀H₁₉NO₄S	V = 1828.60 (9) Å³
M_r = 369.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.9498 (3) Å	µ = 0.20 mm⁻¹
b = 8.8427 (2) Å	T = 293 K
c = 23.2836 (7) Å	0.25 × 0.20 × 0.16 mm
β = 97.085 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5673 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3833 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.968	R_int = 0.026
23203 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.01	Δρ_max = 0.30 e Å⁻³
5673 reflections	Δρ_min = −0.29 e Å⁻³
239 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
C2	0.71830 (17)	0.73053 (17)	0.13969 (7)	0.0461 (3)
C3	0.85936 (15)	0.68775 (16)	0.13101 (6)	0.0406 (3)
C4	0.89541 (15)	0.54808 (16)	0.16149 (6)	0.0408 (3)
C5	0.77241 (15)	0.50989 (17)	0.19043 (6)	0.0430 (3)
C6	0.77105 (19)	0.3804 (2)	0.22371 (7)	0.0587 (4)
H6	0.6889	0.3562	0.2428	0.070*
C7	0.8966 (2)	0.2887 (2)	0.22744 (8)	0.0703 (5)
H7	0.8983	0.2001	0.2490	0.084*
C8	1.0202 (2)	0.3256 (2)	0.19985 (9)	0.0682 (5)
H8	1.1036	0.2621	0.2036	0.082*
C9	1.02144 (17)	0.45440 (19)	0.16699 (7)	0.0546 (4)
H9	1.1050	0.4786	0.1487	0.065*
C10	0.42383 (15)	0.44900 (18)	0.13523 (7)	0.0462 (3)
C11	0.38591 (18)	0.4876 (2)	0.07757 (7)	0.0550 (4)
H11	0.3946	0.5871	0.0655	0.066*
C12	0.3352 (2)	0.3766 (2)	0.03848 (9)	0.0702 (5)
H12	0.3097	0.4009	−0.0003	0.084*
C13	0.3223 (2)	0.2295 (2)	0.05676 (10)	0.0739 (6)
H13	0.2870	0.1553	0.0302	0.089*
C14	0.3607 (2)	0.1917 (2)	0.11349 (11)	0.0720 (5)
H14	0.3524	0.0919	0.1253	0.086*
C15	0.41202 (19)	0.3013 (2)	0.15350 (9)	0.0598 (4)
H15	0.4382	0.2760	0.1922	0.072*
C16	0.6333 (2)	0.8675 (2)	0.11697 (10)	0.0724 (5)
H16A	0.6151	0.9315	0.1487	0.109*
H16B	0.5389	0.8374	0.0960	0.109*
H16C	0.6911	0.9218	0.0916	0.109*
C17	0.96483 (16)	0.77322 (16)	0.09861 (6)	0.0430 (3)
C18	1.0118 (2)	0.92731 (19)	0.12070 (8)	0.0648 (5)
H18A	1.1128	0.9231	0.1400	0.097*
H18B	0.9452	0.9609	0.1474	0.097*
H18C	1.0074	0.9967	0.0888	0.097*
C19	1.01726 (16)	0.70573 (17)	0.05409 (7)	0.0466 (3)
H19	0.9820	0.6090	0.0444	0.056*
C20	1.12631 (18)	0.77169 (18)	0.01894 (7)	0.0497 (4)
C21	1.2556 (2)	0.7283 (2)	−0.06194 (8)	0.0670 (5)
H21A	1.2073	0.7956	−0.0909	0.101*
H21B	1.2938	0.6419	−0.0804	0.101*
H21C	1.3373	0.7801	−0.0395	0.101*
N1	0.66229 (13)	0.62376 (15)	0.17753 (5)	0.0465 (3)
O1	0.48023 (16)	0.53321 (19)	0.24184 (5)	0.0801 (4)
O2	0.40094 (14)	0.72716 (15)	0.16816 (7)	0.0756 (4)
O3	1.1914 (2)	0.88897 (17)	0.02638 (7)	0.0984 (6)
O4	1.14823 (13)	0.67953 (13)	−0.02447 (5)	0.0583 (3)
S1	0.48136 (4)	0.59233 (5)	0.185184 (18)	0.05532 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0440 (7)	0.0399 (7)	0.0552 (8)	−0.0028 (6)	0.0092 (6)	−0.0070 (6)
C3	0.0391 (7)	0.0365 (7)	0.0464 (7)	−0.0050 (6)	0.0066 (5)	−0.0042 (6)
C4	0.0347 (6)	0.0432 (7)	0.0444 (7)	−0.0066 (6)	0.0039 (5)	−0.0023 (6)
C5	0.0372 (7)	0.0527 (8)	0.0390 (7)	−0.0063 (6)	0.0038 (5)	−0.0022 (6)
C6	0.0520 (9)	0.0750 (12)	0.0489 (8)	−0.0117 (8)	0.0058 (7)	0.0168 (8)
C7	0.0648 (11)	0.0738 (13)	0.0695 (11)	−0.0025 (10)	−0.0021 (9)	0.0318 (10)
C8	0.0492 (9)	0.0664 (12)	0.0872 (13)	0.0085 (9)	0.0006 (9)	0.0222 (10)
C9	0.0373 (7)	0.0568 (10)	0.0698 (10)	0.0002 (7)	0.0074 (7)	0.0080 (8)
C10	0.0295 (6)	0.0496 (8)	0.0607 (9)	0.0002 (6)	0.0104 (6)	−0.0014 (7)
C11	0.0497 (9)	0.0484 (9)	0.0661 (10)	−0.0034 (7)	0.0034 (7)	0.0018 (7)
C12	0.0663 (12)	0.0699 (12)	0.0706 (12)	−0.0108 (10)	−0.0063 (9)	−0.0070 (9)
C13	0.0593 (11)	0.0595 (12)	0.0994 (15)	−0.0112 (9)	−0.0042 (10)	−0.0160 (11)
C14	0.0521 (10)	0.0459 (10)	0.1173 (17)	−0.0077 (8)	0.0082 (10)	0.0056 (10)
C15	0.0433 (8)	0.0582 (10)	0.0782 (11)	−0.0038 (7)	0.0079 (8)	0.0114 (9)
C16	0.0593 (11)	0.0506 (10)	0.1084 (16)	0.0094 (8)	0.0149 (10)	0.0063 (10)
C17	0.0406 (7)	0.0369 (7)	0.0511 (8)	−0.0059 (6)	0.0045 (6)	0.0012 (6)
C18	0.0794 (12)	0.0473 (9)	0.0714 (11)	−0.0209 (9)	0.0234 (9)	−0.0137 (8)
C19	0.0461 (8)	0.0376 (7)	0.0576 (8)	−0.0109 (6)	0.0119 (6)	−0.0019 (6)
C20	0.0513 (8)	0.0421 (8)	0.0574 (9)	−0.0096 (7)	0.0139 (7)	−0.0024 (7)
C21	0.0692 (11)	0.0700 (12)	0.0673 (11)	−0.0114 (9)	0.0306 (9)	−0.0010 (9)
N1	0.0389 (6)	0.0512 (7)	0.0510 (7)	−0.0031 (5)	0.0118 (5)	−0.0068 (5)
O1	0.0728 (8)	0.1164 (12)	0.0584 (7)	−0.0149 (8)	0.0369 (6)	−0.0148 (7)
O2	0.0534 (7)	0.0642 (8)	0.1135 (11)	0.0126 (6)	0.0278 (7)	−0.0269 (8)
O3	0.1299 (14)	0.0687 (9)	0.1106 (12)	−0.0562 (9)	0.0702 (10)	−0.0333 (8)
O4	0.0646 (7)	0.0522 (7)	0.0626 (7)	−0.0135 (6)	0.0255 (5)	−0.0074 (5)
S1	0.0418 (2)	0.0660 (3)	0.0624 (3)	−0.00185 (18)	0.02337 (17)	−0.01782 (19)

Geometric parameters (Å, º) top

C2—C3	1.357 (2)	C13—H13	0.93
C2—N1	1.4241 (19)	C14—C15	1.383 (3)
C2—C16	1.493 (2)	C14—H14	0.93
C3—C4	1.441 (2)	C15—H15	0.93
C3—C17	1.4857 (19)	C16—H16A	0.96
C4—C9	1.393 (2)	C16—H16B	0.96
C4—C5	1.4012 (19)	C16—H16C	0.96
C5—C6	1.383 (2)	C17—C19	1.331 (2)
C5—N1	1.415 (2)	C17—C18	1.498 (2)
C6—C7	1.380 (3)	C18—H18A	0.96
C6—H6	0.93	C18—H18B	0.96
C7—C8	1.385 (3)	C18—H18C	0.96
C7—H7	0.93	C19—C20	1.470 (2)
C8—C9	1.373 (2)	C19—H19	0.93
C8—H8	0.93	C20—O3	1.1915 (19)
C9—H9	0.93	C20—O4	1.3315 (19)
C10—C15	1.381 (2)	C21—O4	1.4415 (19)
C10—C11	1.386 (2)	C21—H21A	0.96
C10—S1	1.7540 (16)	C21—H21B	0.96
C11—C12	1.377 (3)	C21—H21C	0.96
C11—H11	0.93	N1—S1	1.6740 (12)
C12—C13	1.378 (3)	O1—S1	1.4202 (14)
C12—H12	0.93	O2—S1	1.4234 (14)
C13—C14	1.365 (3)

C3—C2—N1	108.20 (13)	C10—C15—H15	120.4
C3—C2—C16	128.09 (15)	C14—C15—H15	120.4
N1—C2—C16	123.67 (14)	C2—C16—H16A	109.5
C2—C3—C4	108.77 (12)	C2—C16—H16B	109.5
C2—C3—C17	126.51 (13)	H16A—C16—H16B	109.5
C4—C3—C17	124.64 (12)	C2—C16—H16C	109.5
C9—C4—C5	119.20 (14)	H16A—C16—H16C	109.5
C9—C4—C3	133.22 (14)	H16B—C16—H16C	109.5
C5—C4—C3	107.57 (13)	C19—C17—C3	118.34 (13)
C6—C5—C4	122.05 (14)	C19—C17—C18	124.36 (14)
C6—C5—N1	130.83 (13)	C3—C17—C18	117.20 (13)
C4—C5—N1	107.12 (13)	C17—C18—H18A	109.5
C7—C6—C5	117.28 (15)	C17—C18—H18B	109.5
C7—C6—H6	121.4	H18A—C18—H18B	109.5
C5—C6—H6	121.4	C17—C18—H18C	109.5
C6—C7—C8	121.55 (17)	H18A—C18—H18C	109.5
C6—C7—H7	119.2	H18B—C18—H18C	109.5
C8—C7—H7	119.2	C17—C19—C20	125.32 (14)
C9—C8—C7	121.06 (17)	C17—C19—H19	117.3
C9—C8—H8	119.5	C20—C19—H19	117.3
C7—C8—H8	119.5	O3—C20—O4	121.87 (14)
C8—C9—C4	118.85 (15)	O3—C20—C19	127.63 (15)
C8—C9—H9	120.6	O4—C20—C19	110.48 (13)
C4—C9—H9	120.6	O4—C21—H21A	109.5
C15—C10—C11	120.80 (16)	O4—C21—H21B	109.5
C15—C10—S1	120.41 (13)	H21A—C21—H21B	109.5
C11—C10—S1	118.76 (12)	O4—C21—H21C	109.5
C12—C11—C10	119.07 (17)	H21A—C21—H21C	109.5
C12—C11—H11	120.5	H21B—C21—H21C	109.5
C10—C11—H11	120.5	C5—N1—C2	108.30 (11)
C11—C12—C13	120.15 (19)	C5—N1—S1	121.12 (10)
C11—C12—H12	119.9	C2—N1—S1	126.50 (11)
C13—C12—H12	119.9	C20—O4—C21	116.60 (13)
C14—C13—C12	120.61 (19)	O1—S1—O2	120.37 (9)
C14—C13—H13	119.7	O1—S1—N1	106.13 (7)
C12—C13—H13	119.7	O2—S1—N1	107.09 (8)
C13—C14—C15	120.24 (18)	O1—S1—C10	108.35 (9)
C13—C14—H14	119.9	O2—S1—C10	108.88 (8)
C15—C14—H14	119.9	N1—S1—C10	104.96 (6)
C10—C15—C14	119.12 (18)

N1—C2—C3—C4	2.26 (16)	C2—C3—C17—C18	60.7 (2)
C16—C2—C3—C4	179.74 (16)	C4—C3—C17—C18	−115.44 (17)
N1—C2—C3—C17	−174.38 (13)	C3—C17—C19—C20	−177.59 (14)
C16—C2—C3—C17	3.1 (3)	C18—C17—C19—C20	−1.3 (3)
C2—C3—C4—C9	179.15 (16)	C17—C19—C20—O3	5.1 (3)
C17—C3—C4—C9	−4.1 (3)	C17—C19—C20—O4	−176.02 (15)
C2—C3—C4—C5	−1.70 (16)	C6—C5—N1—C2	−178.24 (16)
C17—C3—C4—C5	175.01 (13)	C4—C5—N1—C2	0.92 (15)
C9—C4—C5—C6	−1.0 (2)	C6—C5—N1—S1	−19.6 (2)
C3—C4—C5—C6	179.68 (14)	C4—C5—N1—S1	159.59 (10)
C9—C4—C5—N1	179.72 (13)	C3—C2—N1—C5	−2.00 (16)
C3—C4—C5—N1	0.44 (15)	C16—C2—N1—C5	−179.62 (15)
C4—C5—C6—C7	−0.1 (2)	C3—C2—N1—S1	−159.21 (11)
N1—C5—C6—C7	178.98 (16)	C16—C2—N1—S1	23.2 (2)
C5—C6—C7—C8	1.0 (3)	O3—C20—O4—C21	0.4 (3)
C6—C7—C8—C9	−0.9 (3)	C19—C20—O4—C21	−178.62 (15)
C7—C8—C9—C4	−0.3 (3)	C5—N1—S1—O1	50.95 (13)
C5—C4—C9—C8	1.2 (2)	C2—N1—S1—O1	−154.49 (13)
C3—C4—C9—C8	−179.75 (17)	C5—N1—S1—O2	−179.29 (11)
C15—C10—C11—C12	0.4 (2)	C2—N1—S1—O2	−24.73 (14)
S1—C10—C11—C12	−177.57 (14)	C5—N1—S1—C10	−63.66 (12)
C10—C11—C12—C13	0.2 (3)	C2—N1—S1—C10	90.89 (13)
C11—C12—C13—C14	−0.6 (3)	C15—C10—S1—O1	−11.22 (15)
C12—C13—C14—C15	0.6 (3)	C11—C10—S1—O1	166.71 (12)
C11—C10—C15—C14	−0.4 (2)	C15—C10—S1—O2	−143.79 (13)
S1—C10—C15—C14	177.49 (13)	C11—C10—S1—O2	34.14 (14)
C13—C14—C15—C10	−0.1 (3)	C15—C10—S1—N1	101.83 (13)
C2—C3—C17—C19	−122.74 (17)	C11—C10—S1—N1	−80.24 (13)
C4—C3—C17—C19	61.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.93	2.58	3.391 (2)	146
C13—H13···O3ⁱⁱ	0.93	2.50	3.277 (2)	141

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉NO₄S
M_r	369.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.9498 (3), 8.8427 (2), 23.2836 (7)
β (°)	97.085 (1)
V (Å³)	1828.60 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.25 × 0.20 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.957, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	23203, 5673, 3833
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.724

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.137, 1.01
No. of reflections	5673
No. of parameters	239
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.29

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.93	2.58	3.391 (2)	146
C13—H13···O3ⁱⁱ	0.93	2.50	3.277 (2)	141

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

Acknowledgements

TK thanks Dr Babu Varghese, SAIF, IIT-Madras, Chennai, India, for his help with the data collection.

References

Bassindale, A. (1984). The Third Dimension in Organic Chemistry, ch. 1, p. 11. New York: John Wiley and Sons. Google Scholar
Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787–797. CSD CrossRef Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chandrakantha, T. N., Puttaraja, & Nethaji, M. (1992). Acta Cryst. C48, 60–62. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Rodriguez, J. G., Temprano, F., Esteban-Calderon, C., Martinez-Ripoll, M. & Garcia-Blanco, S. (1985). Tetrahedron, 41, 3813–3823. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar