3-(1,2-Diphenyl­vinyl)-2-methyl-1-phenyl­sulfonyl-1H-indole

Palani, K.; Jaisankar, P.; Srinivasan, P.C.; Ponnuswamy, M.N.

doi:10.1107/S1600536805041607

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3-(1,2-Diphenylvinyl)-2-methyl-1-phenylsulfonyl-1H-indole

K. Palani, P. Jaisankar, P. C. Srinivasan and M. N. Ponnuswamy

In the title compound, C₂₉H₂₃NO₂S, the bond angles around the S atom indicate a distorted tetrahedral configuration. The crystal structure is stabilized by weak C—H

O and C—H

π hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041607/ci6719sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041607/ci6719Isup2.hkl Contains datablock I

CCDC reference: 296540

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.052
wR factor = 0.137
Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.67 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           27.97
           From the CIF: _reflns_number_total               2905
           Count of symmetry unique reflns         2923
           Completeness (_total/calc)             99.38%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The indole unit is observed in many plants (Nigovic et al., 2000). Indole- 3-acetic acid is a naturally occurring plant growth hormone that controls a number of plant-growth activities (Fargasova, 1994). Many indole- containing natural products are found to exhibit psychotropic (Grinev et al., 1978) and hypertensive (Merk, 1971) properties. A large number of biologically active compounds, mostly those affecting the central nervous system (Zhang & Liebeskind, 1996), contain indolines and their oxidized counterparts as important pharmacophores. Some of the indole derivatives possess antitumour (Schollmeyer et al., 1995) and antibacterial (Okabe & Adachi, 1998) activities. In view of this importance, the crystal structure of the title compound, (I), has been determined and the results are presented here.

A ZORTEP (Zsolnai, 1997) plot of the molecule is shown in Fig.1. The S—O, S—C and S—N bond distances are comparable with the reported values of 1.435 (5), 1.767 (7) and 1.685 (5) Å, respectively (Govindasamy et al., 1998). As observed in other phenylsulfonylindoles (Rodriguez et al., 1995; Govindasamy et al., 1997, 1998), the C—N distances in the indole ring system are longer due to the electron- withdrawing character of the phenylsulfonyl group. The widening of the O1—S1—O2 angle to 119.4 (2)°, and the resultant narrowing of the N1—S1—C10 angle to 104.5 (1)°, from the ideal tetrahedral value, are attributed to the Thorpe–Ingold effect (Bassindale, 1984). The C10–C15, C18–C23 and C25–C30 phenyl rings are oriented at angles of 75.1 (1), 81.3 (1), 59.9 (1)°, respectively, with respect to the indole ring system.

C—H···O-type hydrogen bonds are observed in the molecular structure. The crystal structure is stabilized by intermolecular C—H···O and C—H···π hydrogen bonds (Table 2 and Fig. 2). Cg denotes the centroid of C4–C9 benzene ring.

Experimental top

A solution of 2-methyl-3-diaryl vinylindole (5 mmol) in dry tetrahydrofuran (THF, 10 ml) was added slowly to a stirred suspension of 50% sodium hydride (0.24 g, 10 mmol) in dry THF (4 ml) under nitrogen atmosphere at room temperature. The reaction mixture was refluxed for 3 h and cooled to 268 K. A solution of phenylsulfonyl chloride (1.15 ml, 8 mmol) in dry THF (10 ml) was then added slowly. The solution was then treated with saturated ammonium chloride solution (50 ml) and the organic layer was separated. The aqueous layer was extracted with chloroform (4 x 15 ml), and the combined organic layers were dried over anhydrous Na₂SO₄ and concentrated under reduced pressure to give a white oil. This was crystallized from ethyl acetate and hexane (2:8) to give a crystalline solid (yield 1.59 g (71%), m.p. 427 K). ¹H NMR (400 MHz, CDCl₃): d = 2.24 (s, 3H, CH₃), 6.93–7.58 (m, 18H, Ar—H & 1H vinylic), 8.23–8.25 (d, 1H, J = 8.0 Hz, indole-7H). Mass (m/z %): 449(M+, 75.6), 308 (77.2), 293 (39.1), 230 (100), 217 (10.8), 77 (34.2), 57(10.3).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-labelling scheme. Dashed lines indicate C—H···O hydrogen bonds.
	Fig. 2. The crystal packing of (I), viewed down the a axis. Dashed lines indicate C—H···π interactions.

3-(1,2-Diphenylvinyl)-2-methyl-1-phenylsulfonyl-1H-indole top

Crystal data top

C₂₉H₂₃NO₂S	F(000) = 472
M_r = 449.54	D_x = 1.272 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 9.029 (3) Å	θ = 2.3–28.0°
b = 14.891 (7) Å	µ = 0.16 mm⁻¹
c = 9.8459 (17) Å	T = 293 K
β = 117.588 (18)°	Block, yellow
V = 1173.3 (7) Å³	0.36 × 0.28 × 0.18 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.036
Radiation source: fine-focus sealed tube	θ_max = 28.0°, θ_min = 2.3°
Graphite monochromator	h = 0→11
ω scans	k = 0→19
3078 measured reflections	l = −12→11
2905 independent reflections	3 standard reflections every 60 min
2520 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.1042P)² + 0.0294P] where P = (F_o² + 2F_c²)/3
2905 reflections	(Δ/σ)_max = 0.001
299 parameters	Δρ_max = 0.57 e Å⁻³
1 restraint	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₉H₂₃NO₂S	V = 1173.3 (7) Å³
M_r = 449.54	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.029 (3) Å	µ = 0.16 mm⁻¹
b = 14.891 (7) Å	T = 293 K
c = 9.8459 (17) Å	0.36 × 0.28 × 0.18 mm
β = 117.588 (18)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.036
3078 measured reflections	3 standard reflections every 60 min
2905 independent reflections	intensity decay: none
2520 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.052	1 restraint
wR(F²) = 0.137	H-atom parameters constrained
S = 1.06	Δρ_max = 0.57 e Å⁻³
2905 reflections	Δρ_min = −0.43 e Å⁻³
299 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
S1	−0.01053 (7)	0.07534 (5)	0.39551 (8)	0.03998 (19)
O1	−0.1116 (3)	0.1142 (2)	0.2493 (3)	0.0547 (6)
O2	−0.0602 (3)	0.0833 (2)	0.5127 (3)	0.0553 (6)
N1	0.1761 (3)	0.1241 (2)	0.4600 (3)	0.0381 (5)
C2	0.3054 (3)	0.1152 (2)	0.6152 (3)	0.0390 (6)
C3	0.4550 (3)	0.1171 (2)	0.6152 (3)	0.0368 (6)
C4	0.4279 (3)	0.1246 (2)	0.4598 (3)	0.0344 (5)
C5	0.2559 (3)	0.1279 (2)	0.3656 (3)	0.0346 (5)
C6	0.1891 (4)	0.1386 (3)	0.2081 (3)	0.0473 (7)
H6	0.0743	0.1427	0.1458	0.057*
C7	0.2992 (5)	0.1427 (3)	0.1475 (4)	0.0570 (9)
H7	0.2577	0.1482	0.0420	0.068*
C8	0.4702 (5)	0.1390 (3)	0.2402 (4)	0.0560 (9)
H8	0.5414	0.1429	0.1960	0.067*
C9	0.5366 (4)	0.1296 (3)	0.3964 (4)	0.0476 (7)
H9	0.6516	0.1267	0.4581	0.057*
C10	0.0266 (4)	−0.0384 (2)	0.3737 (4)	0.0429 (6)
C11	0.0085 (6)	−0.0695 (3)	0.2352 (5)	0.0624 (10)
H11	−0.0271	−0.0312	0.1513	0.075*
C12	0.0441 (8)	−0.1588 (3)	0.2225 (6)	0.0775 (13)
H12	0.0327	−0.1803	0.1295	0.093*
C13	0.0954 (7)	−0.2155 (3)	0.3442 (6)	0.0812 (13)
H13	0.1172	−0.2755	0.3341	0.097*
C14	0.1146 (9)	−0.1836 (3)	0.4808 (6)	0.0920 (19)
H14	0.1535	−0.2219	0.5649	0.110*
C15	0.0775 (7)	−0.0953 (3)	0.4973 (5)	0.0692 (12)
H15	0.0868	−0.0748	0.5902	0.083*
C16	0.2723 (4)	0.1129 (3)	0.7500 (4)	0.0559 (9)
H16A	0.3759	0.1058	0.8420	0.084*
H16B	0.1998	0.0633	0.7398	0.084*
H16C	0.2198	0.1680	0.7550	0.084*
C17	0.6222 (4)	0.1124 (2)	0.7518 (3)	0.0407 (6)
C18	0.7218 (4)	0.0304 (2)	0.7618 (3)	0.0410 (6)
C19	0.6437 (5)	−0.0501 (3)	0.6958 (4)	0.0541 (8)
H19	0.5276	−0.0522	0.6421	0.065*
C20	0.7352 (6)	−0.1272 (3)	0.7087 (5)	0.0698 (11)
H20	0.6804	−0.1805	0.6641	0.084*
C21	0.9077 (6)	−0.1253 (3)	0.7873 (5)	0.0667 (11)
H21	0.9696	−0.1770	0.7968	0.080*
C22	0.9863 (5)	−0.0457 (3)	0.8514 (4)	0.0583 (9)
H22	1.1024	−0.0438	0.9044	0.070*
C23	0.8956 (4)	0.0314 (3)	0.8383 (4)	0.0474 (7)
H23	0.9514	0.0846	0.8813	0.057*
C24	0.6775 (4)	0.1740 (2)	0.8629 (3)	0.0453 (7)
H24	0.7796	0.1614	0.9472	0.054*
C25	0.5992 (4)	0.2591 (2)	0.8700 (4)	0.0458 (7)
C26	0.5074 (5)	0.3138 (3)	0.7428 (5)	0.0627 (10)
H26	0.4949	0.2973	0.6470	0.075*
C27	0.4348 (7)	0.3927 (3)	0.7585 (7)	0.0829 (15)
H27	0.3718	0.4278	0.6727	0.099*
C28	0.4555 (7)	0.4192 (4)	0.8998 (8)	0.0843 (15)
H28	0.4061	0.4719	0.9095	0.101*
C29	0.5480 (6)	0.3682 (4)	1.0254 (6)	0.0744 (12)
H29	0.5622	0.3865	1.1210	0.089*
C30	0.6216 (5)	0.2891 (3)	1.0121 (5)	0.0567 (9)
H30	0.6867	0.2556	1.0994	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0222 (3)	0.0509 (4)	0.0441 (3)	0.0026 (3)	0.0130 (2)	0.0020 (3)
O1	0.0289 (10)	0.0639 (15)	0.0556 (13)	0.0077 (10)	0.0063 (9)	0.0103 (12)
O2	0.0366 (10)	0.0700 (16)	0.0692 (15)	0.0010 (12)	0.0329 (11)	−0.0041 (14)
N1	0.0251 (10)	0.0524 (14)	0.0335 (10)	−0.0003 (10)	0.0107 (9)	0.0011 (10)
C2	0.0294 (12)	0.0513 (16)	0.0326 (12)	−0.0024 (12)	0.0112 (10)	0.0006 (12)
C3	0.0272 (12)	0.0487 (15)	0.0301 (12)	−0.0011 (11)	0.0094 (10)	0.0002 (11)
C4	0.0271 (11)	0.0419 (15)	0.0306 (11)	−0.0005 (11)	0.0103 (9)	0.0007 (11)
C5	0.0271 (11)	0.0430 (14)	0.0292 (11)	−0.0016 (11)	0.0092 (9)	−0.0009 (11)
C6	0.0354 (14)	0.070 (2)	0.0280 (12)	−0.0043 (14)	0.0076 (11)	0.0039 (13)
C7	0.0569 (19)	0.079 (3)	0.0339 (14)	−0.0103 (18)	0.0203 (14)	−0.0027 (15)
C8	0.0504 (18)	0.081 (3)	0.0493 (17)	−0.0104 (18)	0.0339 (15)	−0.0052 (17)
C9	0.0326 (13)	0.064 (2)	0.0478 (16)	−0.0033 (14)	0.0199 (12)	−0.0031 (15)
C10	0.0337 (13)	0.0457 (16)	0.0486 (16)	−0.0006 (12)	0.0185 (12)	0.0009 (13)
C11	0.078 (3)	0.061 (2)	0.0531 (19)	0.001 (2)	0.0350 (19)	0.0048 (17)
C12	0.107 (4)	0.065 (3)	0.077 (3)	0.000 (3)	0.056 (3)	−0.007 (2)
C13	0.104 (4)	0.053 (2)	0.088 (3)	0.004 (2)	0.045 (3)	0.004 (2)
C14	0.142 (5)	0.053 (2)	0.068 (3)	0.014 (3)	0.038 (3)	0.014 (2)
C15	0.098 (3)	0.060 (2)	0.050 (2)	0.001 (2)	0.034 (2)	0.0065 (17)
C16	0.0464 (17)	0.086 (3)	0.0395 (15)	−0.0076 (17)	0.0230 (13)	−0.0011 (17)
C17	0.0302 (12)	0.0508 (16)	0.0343 (13)	0.0020 (12)	0.0092 (11)	0.0050 (12)
C18	0.0356 (14)	0.0512 (17)	0.0318 (12)	0.0039 (13)	0.0119 (11)	0.0060 (12)
C19	0.0427 (16)	0.0535 (19)	0.0521 (17)	0.0039 (14)	0.0099 (14)	0.0010 (15)
C20	0.066 (2)	0.054 (2)	0.071 (2)	0.005 (2)	0.015 (2)	−0.002 (2)
C21	0.067 (2)	0.066 (2)	0.069 (2)	0.026 (2)	0.033 (2)	0.013 (2)
C22	0.0431 (17)	0.079 (3)	0.0535 (18)	0.0178 (18)	0.0233 (15)	0.0149 (19)
C23	0.0347 (13)	0.065 (2)	0.0391 (14)	0.0035 (14)	0.0138 (11)	0.0036 (14)
C24	0.0330 (13)	0.0542 (17)	0.0352 (13)	0.0034 (13)	0.0044 (11)	0.0017 (13)
C25	0.0376 (14)	0.0486 (16)	0.0448 (15)	−0.0025 (13)	0.0138 (12)	−0.0016 (13)
C26	0.064 (2)	0.052 (2)	0.054 (2)	0.0035 (18)	0.0123 (18)	0.0045 (16)
C27	0.075 (3)	0.054 (2)	0.086 (3)	0.018 (2)	0.010 (2)	0.008 (2)
C28	0.078 (3)	0.059 (3)	0.117 (4)	0.010 (2)	0.045 (3)	−0.013 (3)
C29	0.084 (3)	0.069 (3)	0.080 (3)	−0.005 (3)	0.046 (3)	−0.018 (2)
C30	0.056 (2)	0.060 (2)	0.0528 (19)	−0.0028 (17)	0.0235 (16)	−0.0046 (16)

Geometric parameters (Å, º) top

S1—O1	1.423 (2)	C15—H15	0.93
S1—O2	1.423 (2)	C16—H16A	0.96
S1—N1	1.667 (2)	C16—H16B	0.96
S1—C10	1.759 (4)	C16—H16C	0.96
N1—C5	1.417 (3)	C17—C24	1.335 (5)
N1—C2	1.436 (3)	C17—C18	1.492 (5)
C2—C3	1.351 (4)	C18—C19	1.390 (5)
C2—C16	1.490 (4)	C18—C23	1.391 (4)
C3—C4	1.438 (4)	C19—C20	1.387 (6)
C3—C17	1.487 (4)	C19—H19	0.93
C4—C9	1.388 (4)	C20—C21	1.381 (7)
C4—C5	1.393 (3)	C20—H20	0.93
C5—C6	1.389 (4)	C21—C22	1.375 (7)
C6—C7	1.377 (5)	C21—H21	0.93
C6—H6	0.93	C22—C23	1.381 (6)
C7—C8	1.383 (5)	C22—H22	0.93
C7—H7	0.93	C23—H23	0.93
C8—C9	1.375 (5)	C24—C25	1.468 (5)
C8—H8	0.93	C24—H24	0.93
C9—H9	0.93	C25—C30	1.391 (5)
C10—C15	1.375 (5)	C25—C26	1.400 (5)
C10—C11	1.376 (5)	C26—C27	1.387 (7)
C11—C12	1.387 (7)	C26—H26	0.93
C11—H11	0.93	C27—C28	1.373 (9)
C12—C13	1.359 (7)	C27—H27	0.93
C12—H12	0.93	C28—C29	1.359 (8)
C13—C14	1.359 (8)	C28—H28	0.93
C13—H13	0.93	C29—C30	1.388 (7)
C14—C15	1.386 (7)	C29—H29	0.93
C14—H14	0.93	C30—H30	0.93

O1—S1—O2	119.43 (15)	C14—C15—H15	120.6
O1—S1—N1	105.63 (14)	C2—C16—H16A	109.5
O2—S1—N1	107.29 (14)	C2—C16—H16B	109.5
O1—S1—C10	109.71 (17)	H16A—C16—H16B	109.5
O2—S1—C10	109.22 (17)	C2—C16—H16C	109.5
N1—S1—C10	104.47 (14)	H16A—C16—H16C	109.5
C5—N1—C2	106.9 (2)	H16B—C16—H16C	109.5
C5—N1—S1	119.93 (19)	C24—C17—C3	123.1 (3)
C2—N1—S1	123.1 (2)	C24—C17—C18	121.5 (3)
C3—C2—N1	108.6 (2)	C3—C17—C18	115.3 (3)
C3—C2—C16	127.8 (3)	C19—C18—C23	117.6 (3)
N1—C2—C16	123.4 (2)	C19—C18—C17	121.0 (3)
C2—C3—C4	108.9 (2)	C23—C18—C17	121.4 (3)
C2—C3—C17	126.5 (3)	C20—C19—C18	121.3 (3)
C4—C3—C17	124.5 (2)	C20—C19—H19	119.3
C9—C4—C5	120.1 (3)	C18—C19—H19	119.3
C9—C4—C3	132.5 (3)	C21—C20—C19	120.2 (4)
C5—C4—C3	107.4 (2)	C21—C20—H20	119.9
C6—C5—C4	121.4 (3)	C19—C20—H20	119.9
C6—C5—N1	130.3 (2)	C22—C21—C20	118.9 (4)
C4—C5—N1	108.1 (2)	C22—C21—H21	120.5
C7—C6—C5	117.5 (3)	C20—C21—H21	120.5
C7—C6—H6	121.3	C21—C22—C23	121.0 (4)
C5—C6—H6	121.3	C21—C22—H22	119.5
C6—C7—C8	121.4 (3)	C23—C22—H22	119.5
C6—C7—H7	119.3	C22—C23—C18	120.9 (4)
C8—C7—H7	119.3	C22—C23—H23	119.6
C9—C8—C7	121.2 (3)	C18—C23—H23	119.6
C9—C8—H8	119.4	C17—C24—C25	128.8 (3)
C7—C8—H8	119.4	C17—C24—H24	115.6
C8—C9—C4	118.4 (3)	C25—C24—H24	115.6
C8—C9—H9	120.8	C30—C25—C26	117.6 (4)
C4—C9—H9	120.8	C30—C25—C24	118.5 (3)
C15—C10—C11	120.5 (4)	C26—C25—C24	123.9 (3)
C15—C10—S1	119.3 (3)	C27—C26—C25	120.5 (4)
C11—C10—S1	120.2 (3)	C27—C26—H26	119.7
C10—C11—C12	119.1 (4)	C25—C26—H26	119.7
C10—C11—H11	120.5	C28—C27—C26	120.4 (5)
C12—C11—H11	120.5	C28—C27—H27	119.8
C13—C12—C11	121.0 (5)	C26—C27—H27	119.8
C13—C12—H12	119.5	C29—C28—C27	120.0 (4)
C11—C12—H12	119.5	C29—C28—H28	120.0
C12—C13—C14	119.4 (5)	C27—C28—H28	120.0
C12—C13—H13	120.3	C28—C29—C30	120.5 (5)
C14—C13—H13	120.3	C28—C29—H29	119.8
C13—C14—C15	121.4 (4)	C30—C29—H29	119.8
C13—C14—H14	119.3	C29—C30—C25	121.0 (4)
C15—C14—H14	119.3	C29—C30—H30	119.5
C10—C15—C14	118.7 (4)	C25—C30—H30	119.5
C10—C15—H15	120.6

O1—S1—N1—C5	−50.4 (3)	N1—S1—C10—C11	−92.3 (3)
O2—S1—N1—C5	−178.8 (2)	C15—C10—C11—C12	−0.7 (7)
C10—S1—N1—C5	65.3 (3)	S1—C10—C11—C12	177.8 (4)
O1—S1—N1—C2	168.7 (3)	C10—C11—C12—C13	0.3 (8)
O2—S1—N1—C2	40.3 (3)	C11—C12—C13—C14	−1.1 (9)
C10—S1—N1—C2	−75.6 (3)	C12—C13—C14—C15	2.2 (10)
C5—N1—C2—C3	2.3 (4)	C11—C10—C15—C14	1.8 (8)
S1—N1—C2—C3	147.4 (2)	S1—C10—C15—C14	−176.7 (5)
C5—N1—C2—C16	177.4 (3)	C13—C14—C15—C10	−2.6 (10)
S1—N1—C2—C16	−37.5 (4)	C2—C3—C17—C24	−62.0 (5)
N1—C2—C3—C4	−1.7 (4)	C4—C3—C17—C24	118.0 (4)
C16—C2—C3—C4	−176.5 (3)	C2—C3—C17—C18	114.4 (4)
N1—C2—C3—C17	178.3 (3)	C4—C3—C17—C18	−65.5 (4)
C16—C2—C3—C17	3.5 (6)	C24—C17—C18—C19	148.5 (3)
C2—C3—C4—C9	179.6 (4)	C3—C17—C18—C19	−28.1 (4)
C17—C3—C4—C9	−0.4 (6)	C24—C17—C18—C23	−30.9 (4)
C2—C3—C4—C5	0.5 (4)	C3—C17—C18—C23	152.6 (3)
C17—C3—C4—C5	−179.5 (3)	C23—C18—C19—C20	1.4 (6)
C9—C4—C5—C6	−1.7 (5)	C17—C18—C19—C20	−178.0 (4)
C3—C4—C5—C6	177.5 (3)	C18—C19—C20—C21	−0.4 (7)
C9—C4—C5—N1	−178.3 (3)	C19—C20—C21—C22	−0.4 (7)
C3—C4—C5—N1	1.0 (3)	C20—C21—C22—C23	0.1 (7)
C2—N1—C5—C6	−178.2 (3)	C21—C22—C23—C18	0.9 (6)
S1—N1—C5—C6	35.4 (5)	C19—C18—C23—C22	−1.7 (5)
C2—N1—C5—C4	−2.0 (3)	C17—C18—C23—C22	177.7 (3)
S1—N1—C5—C4	−148.4 (2)	C3—C17—C24—C25	−5.7 (6)
C4—C5—C6—C7	2.1 (5)	C18—C17—C24—C25	178.1 (3)
N1—C5—C6—C7	177.9 (4)	C17—C24—C25—C30	146.4 (4)
C5—C6—C7—C8	−1.8 (6)	C17—C24—C25—C26	−35.8 (6)
C6—C7—C8—C9	1.0 (7)	C30—C25—C26—C27	−3.3 (6)
C7—C8—C9—C4	−0.5 (6)	C24—C25—C26—C27	179.0 (4)
C5—C4—C9—C8	0.8 (5)	C25—C26—C27—C28	1.6 (8)
C3—C4—C9—C8	−178.2 (4)	C26—C27—C28—C29	0.3 (9)
O1—S1—C10—C15	−160.9 (3)	C27—C28—C29—C30	−0.3 (8)
O2—S1—C10—C15	−28.3 (4)	C28—C29—C30—C25	−1.5 (7)
N1—S1—C10—C15	86.2 (3)	C26—C25—C30—C29	3.2 (6)
O1—S1—C10—C11	20.5 (4)	C24—C25—C30—C29	−178.9 (4)
O2—S1—C10—C11	153.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.37	2.948 (5)	120
C9—H9···O2ⁱ	0.93	2.49	3.344 (5)	153
C16—H16B···O2	0.96	2.40	2.858 (5)	109
C20—H20···Cgⁱⁱ	0.93	2.83	3.658 (5)	148

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

Experimental details

Crystal data
Chemical formula	C₂₉H₂₃NO₂S
M_r	449.54
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	9.029 (3), 14.891 (7), 9.8459 (17)
β (°)	117.588 (18)
V (Å³)	1173.3 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.36 × 0.28 × 0.18

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3078, 2905, 2520
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.137, 1.06
No. of reflections	2905
No. of parameters	299
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.43

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997), PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

S1—O1	1.423 (2)	S1—C10	1.759 (4)
S1—O2	1.423 (2)	N1—C5	1.417 (3)
S1—N1	1.667 (2)	N1—C2	1.436 (3)

O1—S1—N1—C5	−50.4 (3)	C10—S1—N1—C5	65.3 (3)
O2—S1—N1—C5	−178.8 (2)	O1—S1—N1—C2	168.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.37	2.948 (5)	120
C9—H9···O2ⁱ	0.93	2.49	3.344 (5)	153
C16—H16B···O2	0.96	2.40	2.858 (5)	109
C20—H20···Cgⁱⁱ	0.93	2.83	3.658 (5)	148

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

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