Ethyl 3-[2-(3,4-dimeth­oxy­benz­yl)-1-phenyl­sulfonyl-1H-indol-3-yl]acrylate chloro­form hemisolvate

Thenmozhi, M.; Kavitha, T.; Dhayalan, V.; Mohanakrishnan, A.K.; Ponnuswamy, M.N.

doi:10.1107/S1600536811017740

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1460-o1461

doi:10.1107/S1600536811017740

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Ethyl 3-[2-(3,4-dimethoxybenzyl)-1-phenylsulfonyl-1H-indol-3-yl]acrylate chloroform hemisolvate

M. Thenmozhi,^a T. Kavitha,^a V. Dhayalan,^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 4 April 2011; accepted 11 May 2011; online 20 May 2011)

In the title compound, C₂₈H₂₇NO₆S·0.5CHCl₃, the ethyl acrylate substituent adopts an extented conformation with all torsion angles close to 180°. The chloroform solvent molecule is disordered across an inversion centre and is therefore half occupied. The molecular packing is controlled by intermolecular C—H⋯O interactions.

Related literature

For general background to indoles, see: Hu et al. (2005 ); Nieto et al. (2005 ); Mathiesen et al. (2005 ); Olgen & Nebioglu (2002 ). For the sulfonyl moiety, see: Bassindale (1984 ). For hybridization, see: Beddoes et al. (1986 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₈H₂₇NO₆S·0.5CHCl₃
M_r = 565.25
Triclinic, $[P \overline 1]$
a = 10.2154 (3) Å
b = 12.0504 (4) Å
c = 12.6310 (4) Å
α = 70.602 (2)°
β = 69.613 (1)°
γ = 77.056 (2)°
V = 1364.39 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.913, T_max = 0.941
38797 measured reflections
10612 independent reflections
7709 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.189
S = 1.04
10612 reflections
364 parameters
27 restraints
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O4ⁱ	0.93	2.53	3.411 (3)	159
C24—H24B⋯O7ⁱⁱ	0.96	2.51	3.461 (2)	169
C24—H24A⋯O7ⁱⁱⁱ	0.96	2.52	3.367 (3)	147
C30—H30A⋯O3^iv	0.96	2.59	3.429 (7)	146
C30—H30A⋯O4^iv	0.96	2.55	3.424 (7)	151
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z+1; (iii) -x+1, -y+1, -z; (iv) 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: SHELXS97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811017740/bt5508sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017740/bt5508Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017740/bt5508Isup3.cml

checkCIF report

Comment top

Carboxylic acid indoles act as inhibitors of plasminogen activator inhibitor-1 (Hu et al., 2005). The benzenesulfonamide group attached to the indole ring exhibit significant biological activities, such as antibacterial etc., (Nieto et al., 2005). Also, the indole derivatives are identified as the molecules which interfere with a G protein-independent signaling pathway of the CRTH2 receptor (Mathiesen et al.,2005). N-substituted indole carboxylic acid esters have been prepared as possible cyclo-oxygenase-2 (COX-2) enzyme inhibitors (Olgen & Nebioglu, 2002).

Fig.1 shows the ORTEP plot of the title compound. The indole moiety is planar with the maximum deviation of -0.033 (2)Å and 0.028 (2)Å for atoms C5 and C7, respectively. The indole ring system is oriented equatorially to the phenyl sulfonyl ring [dihedral angle = 78.18 (6)°]. The O—S—O and N—S—C angles [See Table1] deviate significantly from their ideal value due to the Thrope-Ingold effect (Bassindale, 1984). The dimethoxybenzyl group is also equatorially oriented to the planar indole ring, which can be observed from the dihedral angle [78.04 (4)°].

The ethyl acrylate group substituted at C3 position of the indole ring takes up an extented conformation which is evident from the torsion angle values [C25—C26—C27—O8 =] -179.10 (16)°; [C25—C26—C27- O7 =] 1.8 (3)°; [C26—C27—O8—C28 =] 179.8 (2)°; [C29—C28—O8—C27 =] 179.7 (2)°. The sum of the bond angles around N1[359.37°] shows that atom N1 exhibits sp² hybridization (Beddoes et al., 1986). The chloroform solvent is disordered across inversion centre with the site occupancies of 0.5 for each.

The molecular packing is controlled by intra and intermolecular C—H···O interactions in addition to van der Waals forces (Table 2). Atom H15 of C15 form an intermolecular hydrogen bonding with atom O4, leading to a C11 linear chains (Bernstein et al., 1995) with C—H···O type of interactions running along a-axis. The intermolecular interaction C24—H24A···O7 leads to R₂²(13) dimers, which are connected through C24—H24B···O7 interaction as closed loops running along c-axis. Intermolecular bifurcated C—H···O hydrogen bonds involving the two oxygen atoms of the dimethoxybenzyl group and the hydrogen atom of the chloroform, solvent generates R₁²(5) ring motif (Fig.2).

Related literature top

For general background to indoles, see: Hu et al. (2005); Nieto et al. (2005); Mathiesen et al. (2005); Olgen & Nebioglu (2002). For the sulfonyl moiety, see: Bassindale (1984). For hybridization, see: Beddoes et al. (1986). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

To a solution of (E)-Ethyl 3-(2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl) acrylate (0.3 g, 0.66 mmol) in dry DME (10 ml), ZnBr₂ (0.3 g, 1.3 mmol), K₂CO₃ (0.18 g, 1.33 mmol) and veratrole (0.11 g, 0.79 mmol) were added. The reaction mixture was then refluxed for 12hrs under N₂ atmosphere. The solvent was removed and the reaction mixture was quenched with ice-water (100 mL) containing 2 mL of conc.HCl. It was then extracted with chloroform (20 mL) and dried (Na₂SO₄). Removal of the solvent followed by crystallization from methanol afforded the product as pale yellow 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: SHELXS97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The ORTEP plot of the title compound, showing 30% probability displacement ellipsoids. H atoms omitted for clarity.
	Fig. 2. The packing of the molecules showing intermolecular C—H···O hydrogen bonds (dashed lines).

Ethyl 3-[2-(3,4-dimethoxybenzyl)-1-phenylsulfonyl-1H-indol-3-yl]prop-2-enoate chloroform hemisolvate top

Crystal data top

C₂₈H₂₇NO₆S·0.5CHCl₃	Z = 2
M_r = 565.25	F(000) = 590
Triclinic, P1	D_x = 1.376 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2154 (3) Å	Cell parameters from 10612 reflections
b = 12.0504 (4) Å	θ = 1.8–34.4°
c = 12.6310 (4) Å	µ = 0.31 mm⁻¹
α = 70.602 (2)°	T = 293 K
β = 69.613 (1)°	Block, yellow
γ = 77.056 (2)°	0.30 × 0.25 × 0.20 mm
V = 1364.39 (7) Å³

Data collection top

Bruker Kappa APEXII area-detector diffractometer	10612 independent reflections
Radiation source: fine-focus sealed tube	7709 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and ϕ scans	θ_max = 34.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −15→16
T_min = 0.913, T_max = 0.941	k = −18→18
38797 measured reflections	l = −18→19

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.189	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1059P)² + 0.3616P] where P = (F_o² + 2F_c²)/3
10612 reflections	(Δ/σ)_max = 0.005
364 parameters	Δρ_max = 0.73 e Å⁻³
27 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₂₈H₂₇NO₆S·0.5CHCl₃	γ = 77.056 (2)°
M_r = 565.25	V = 1364.39 (7) Å³
Triclinic, P1	Z = 2
a = 10.2154 (3) Å	Mo Kα radiation
b = 12.0504 (4) Å	µ = 0.31 mm⁻¹
c = 12.6310 (4) Å	T = 293 K
α = 70.602 (2)°	0.30 × 0.25 × 0.20 mm
β = 69.613 (1)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	10612 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	7709 reflections with I > 2σ(I)
T_min = 0.913, T_max = 0.941	R_int = 0.026
38797 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	27 restraints
wR(F²) = 0.189	H-atom parameters constrained
S = 1.04	Δρ_max = 0.73 e Å⁻³
10612 reflections	Δρ_min = −0.46 e Å⁻³
364 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	Occ. (<1)
C2	0.72857 (13)	0.61852 (12)	0.05863 (12)	0.0264 (2)
C3	0.81718 (13)	0.63351 (12)	−0.05351 (12)	0.0274 (2)
C4	0.95289 (13)	0.65050 (12)	−0.05427 (12)	0.0263 (2)
C5	1.07996 (14)	0.66763 (13)	−0.14331 (13)	0.0315 (3)
H5	1.0889	0.6670	−0.2189	0.038*
C6	1.19275 (15)	0.68563 (15)	−0.11662 (15)	0.0364 (3)
H6	1.2784	0.6974	−0.1750	0.044*
C7	1.17913 (15)	0.68629 (15)	−0.00368 (16)	0.0379 (3)
H7	1.2559	0.7000	0.0116	0.045*
C8	1.05530 (15)	0.66722 (15)	0.08678 (14)	0.0356 (3)
H8	1.0476	0.6666	0.1625	0.043*
C9	0.94241 (13)	0.64898 (12)	0.05935 (12)	0.0279 (2)
C10	0.70544 (17)	0.78432 (16)	0.26272 (14)	0.0377 (3)
C11	0.5742 (2)	0.84292 (17)	0.25639 (15)	0.0432 (4)
H11	0.5084	0.8035	0.2523	0.052*
C12	0.5421 (3)	0.9606 (2)	0.2561 (2)	0.0574 (5)
H12	0.4541	1.0006	0.2523	0.069*
C13	0.6404 (3)	1.0186 (2)	0.2616 (3)	0.0744 (8)
H13	0.6187	1.0980	0.2609	0.089*
C14	0.7695 (3)	0.9599 (3)	0.2680 (3)	0.0806 (9)
H14	0.8348	0.9999	0.2720	0.097*
C15	0.8049 (2)	0.8418 (2)	0.2685 (2)	0.0587 (6)
H15	0.8931	0.8022	0.2727	0.070*
C16	0.58220 (13)	0.58587 (12)	0.10469 (13)	0.0292 (3)
H16A	0.5727	0.5253	0.1792	0.035*
H16B	0.5688	0.5514	0.0504	0.035*
C17	0.46644 (13)	0.68702 (12)	0.12265 (12)	0.0269 (2)
C18	0.47327 (14)	0.79830 (13)	0.04363 (13)	0.0312 (3)
H18	0.5530	0.8133	−0.0208	0.037*
C19	0.36222 (16)	0.88845 (13)	0.05909 (14)	0.0347 (3)
H19	0.3682	0.9628	0.0047	0.042*
C20	0.24365 (15)	0.86818 (14)	0.15431 (15)	0.0350 (3)
C21	0.23710 (14)	0.75648 (14)	0.23783 (13)	0.0326 (3)
C22	0.34699 (14)	0.66710 (13)	0.22105 (12)	0.0296 (3)
H22	0.3417	0.5928	0.2756	0.036*
C23	0.1240 (3)	1.0559 (2)	0.0848 (3)	0.0857 (10)
H23A	0.1932	1.1019	0.0787	0.129*
H23B	0.0323	1.1002	0.1029	0.129*
H23C	0.1440	1.0385	0.0115	0.129*
C24	0.1089 (2)	0.6366 (2)	0.42176 (19)	0.0577 (5)
H24A	0.1140	0.5729	0.3903	0.087*
H24B	0.0213	0.6415	0.4826	0.087*
H24C	0.1855	0.6224	0.4539	0.087*
C25	0.79102 (15)	0.63214 (13)	−0.15877 (13)	0.0311 (3)
H25	0.8700	0.6102	−0.2158	0.037*
C26	0.67095 (15)	0.65761 (15)	−0.18607 (13)	0.0342 (3)
H26	0.5864	0.6751	−0.1316	0.041*
C27	0.67332 (16)	0.65776 (16)	−0.30294 (13)	0.0358 (3)
C28	0.5395 (2)	0.6890 (3)	−0.43115 (17)	0.0634 (6)
H28A	0.5753	0.6117	−0.4448	0.076*
H28B	0.5976	0.7465	−0.4927	0.076*
C29	0.3931 (3)	0.7211 (3)	−0.4337 (2)	0.0673 (7)
H29A	0.3356	0.6655	−0.3710	0.101*
H29B	0.3881	0.7196	−0.5077	0.101*
H29C	0.3599	0.7993	−0.4242	0.101*
N1	0.80387 (12)	0.62707 (11)	0.13020 (10)	0.0292 (2)
O1	0.61261 (13)	0.58330 (11)	0.31986 (10)	0.0420 (3)
O2	0.85541 (15)	0.58180 (14)	0.31850 (11)	0.0509 (3)
O3	0.12766 (14)	0.94873 (12)	0.17533 (14)	0.0550 (4)
O4	0.11775 (12)	0.74569 (12)	0.33019 (12)	0.0468 (3)
O7	0.77576 (14)	0.63380 (17)	−0.37800 (13)	0.0608 (4)
O8	0.54527 (12)	0.68657 (14)	−0.31723 (10)	0.0482 (3)
S1	0.74189 (4)	0.63276 (4)	0.26998 (3)	0.03379 (10)
C30	1.0269 (8)	−0.0254 (6)	0.4558 (6)	0.113 (3)	0.50
H30A	1.0428	−0.0660	0.3979	0.136*	0.50
Cl1	0.9317 (6)	0.1115 (4)	0.4302 (5)	0.199 (2)	0.50
Cl2	0.9683 (8)	−0.1068 (4)	0.5950 (4)	0.223 (3)	0.50
Cl3	1.1858 (5)	0.0222 (6)	0.4566 (6)	0.241 (2)	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0239 (5)	0.0266 (6)	0.0284 (6)	−0.0029 (4)	−0.0068 (4)	−0.0083 (5)
C3	0.0237 (5)	0.0287 (6)	0.0294 (6)	−0.0024 (4)	−0.0067 (4)	−0.0093 (5)
C4	0.0233 (5)	0.0246 (6)	0.0297 (6)	−0.0015 (4)	−0.0063 (4)	−0.0084 (5)
C5	0.0256 (6)	0.0342 (7)	0.0311 (6)	−0.0035 (5)	−0.0032 (5)	−0.0102 (5)
C6	0.0237 (6)	0.0394 (8)	0.0433 (8)	−0.0042 (5)	−0.0032 (5)	−0.0149 (6)
C7	0.0250 (6)	0.0452 (8)	0.0483 (9)	−0.0049 (5)	−0.0097 (6)	−0.0199 (7)
C8	0.0286 (6)	0.0450 (8)	0.0383 (8)	−0.0033 (5)	−0.0102 (5)	−0.0186 (6)
C9	0.0242 (5)	0.0283 (6)	0.0311 (6)	−0.0017 (4)	−0.0072 (4)	−0.0102 (5)
C10	0.0395 (7)	0.0459 (8)	0.0285 (7)	−0.0127 (6)	−0.0010 (5)	−0.0162 (6)
C11	0.0526 (9)	0.0454 (9)	0.0356 (8)	−0.0058 (7)	−0.0139 (7)	−0.0158 (7)
C12	0.0707 (13)	0.0472 (11)	0.0538 (12)	−0.0002 (9)	−0.0168 (10)	−0.0197 (9)
C13	0.0876 (18)	0.0528 (13)	0.0797 (18)	−0.0212 (12)	0.0009 (14)	−0.0335 (12)
C14	0.0689 (15)	0.0828 (18)	0.102 (2)	−0.0386 (14)	0.0080 (14)	−0.0570 (17)
C15	0.0406 (9)	0.0773 (15)	0.0694 (14)	−0.0203 (9)	0.0008 (8)	−0.0441 (12)
C16	0.0246 (5)	0.0294 (6)	0.0327 (6)	−0.0057 (4)	−0.0051 (5)	−0.0095 (5)
C17	0.0223 (5)	0.0303 (6)	0.0278 (6)	−0.0055 (4)	−0.0055 (4)	−0.0081 (5)
C18	0.0268 (6)	0.0339 (7)	0.0293 (6)	−0.0069 (5)	−0.0041 (5)	−0.0066 (5)
C19	0.0325 (6)	0.0293 (7)	0.0364 (7)	−0.0056 (5)	−0.0072 (5)	−0.0038 (5)
C20	0.0287 (6)	0.0310 (7)	0.0409 (8)	−0.0015 (5)	−0.0059 (5)	−0.0104 (6)
C21	0.0250 (6)	0.0362 (7)	0.0332 (7)	−0.0061 (5)	−0.0021 (5)	−0.0104 (6)
C22	0.0260 (5)	0.0300 (6)	0.0296 (6)	−0.0064 (4)	−0.0052 (5)	−0.0055 (5)
C23	0.0520 (12)	0.0391 (11)	0.113 (2)	0.0090 (9)	0.0024 (13)	0.0079 (12)
C24	0.0444 (9)	0.0549 (11)	0.0452 (10)	−0.0098 (8)	0.0117 (8)	−0.0017 (8)
C25	0.0298 (6)	0.0364 (7)	0.0278 (6)	−0.0047 (5)	−0.0068 (5)	−0.0110 (5)
C26	0.0302 (6)	0.0446 (8)	0.0295 (6)	−0.0017 (5)	−0.0078 (5)	−0.0156 (6)
C27	0.0322 (6)	0.0477 (8)	0.0293 (7)	−0.0073 (6)	−0.0066 (5)	−0.0141 (6)
C28	0.0493 (10)	0.116 (2)	0.0294 (8)	−0.0157 (11)	−0.0110 (7)	−0.0228 (10)
C29	0.0630 (13)	0.103 (2)	0.0438 (11)	−0.0165 (13)	−0.0262 (10)	−0.0151 (12)
N1	0.0253 (5)	0.0349 (6)	0.0271 (5)	−0.0041 (4)	−0.0054 (4)	−0.0106 (4)
O1	0.0429 (6)	0.0477 (7)	0.0297 (5)	−0.0165 (5)	−0.0017 (4)	−0.0060 (5)
O2	0.0485 (7)	0.0687 (9)	0.0352 (6)	−0.0030 (6)	−0.0203 (5)	−0.0084 (6)
O3	0.0369 (6)	0.0367 (6)	0.0681 (9)	0.0056 (5)	0.0009 (6)	−0.0092 (6)
O4	0.0319 (5)	0.0444 (7)	0.0440 (7)	−0.0035 (5)	0.0078 (5)	−0.0077 (5)
O7	0.0395 (7)	0.1053 (13)	0.0413 (7)	−0.0004 (7)	−0.0046 (5)	−0.0383 (8)
O8	0.0346 (6)	0.0831 (10)	0.0283 (5)	−0.0080 (6)	−0.0089 (4)	−0.0174 (6)
S1	0.03402 (18)	0.0409 (2)	0.02481 (17)	−0.00679 (14)	−0.00670 (12)	−0.00787 (14)
C30	0.145 (6)	0.099 (5)	0.098 (5)	0.038 (4)	−0.053 (4)	−0.047 (4)
Cl1	0.273 (5)	0.147 (3)	0.235 (5)	0.091 (3)	−0.201 (5)	−0.071 (3)
Cl2	0.327 (6)	0.129 (3)	0.147 (3)	−0.070 (4)	0.001 (4)	−0.003 (2)
Cl3	0.162 (3)	0.292 (6)	0.246 (5)	0.010 (4)	−0.066 (3)	−0.065 (4)

Geometric parameters (Å, º) top

C2—C3	1.3669 (19)	C23—O3	1.416 (3)
C2—N1	1.4146 (17)	C23—H23A	0.9600
C2—C16	1.4948 (17)	C23—H23B	0.9600
C3—C4	1.4424 (17)	C23—H23C	0.9600
C3—C25	1.4503 (19)	C24—O4	1.430 (2)
C4—C5	1.3932 (18)	C24—H24A	0.9600
C4—C9	1.3956 (19)	C24—H24B	0.9600
C5—C6	1.385 (2)	C24—H24C	0.9600
C5—H5	0.9300	C25—C26	1.332 (2)
C6—C7	1.387 (2)	C25—H25	0.9300
C6—H6	0.9300	C26—C27	1.467 (2)
C7—C8	1.381 (2)	C26—H26	0.9300
C7—H7	0.9300	C27—O7	1.1969 (19)
C8—C9	1.3931 (19)	C27—O8	1.3355 (19)
C8—H8	0.9300	C28—O8	1.451 (2)
C9—N1	1.4148 (17)	C28—C29	1.467 (3)
C10—C11	1.384 (3)	C28—H28A	0.9700
C10—C15	1.385 (2)	C28—H28B	0.9700
C10—S1	1.7581 (18)	C29—H29A	0.9600
C11—C12	1.381 (3)	C29—H29B	0.9600
C11—H11	0.9300	C29—H29C	0.9600
C12—C13	1.377 (4)	N1—S1	1.6749 (12)
C12—H12	0.9300	O1—S1	1.4211 (12)
C13—C14	1.366 (4)	O2—S1	1.4225 (13)
C13—H13	0.9300	C30—C30ⁱ	1.341 (14)
C14—C15	1.387 (4)	C30—Cl2ⁱ	1.512 (8)
C14—H14	0.9300	C30—Cl1ⁱ	1.601 (8)
C15—H15	0.9300	C30—Cl2	1.673 (7)
C16—C17	1.5121 (19)	C30—Cl1	1.708 (6)
C16—H16A	0.9700	C30—Cl3	1.842 (8)
C16—H16B	0.9700	C30—Cl3ⁱ	2.065 (10)
C17—C18	1.380 (2)	C30—H30A	0.9600
C17—C22	1.4028 (18)	Cl1—Cl2ⁱ	0.952 (7)
C18—C19	1.393 (2)	Cl1—C30ⁱ	1.601 (8)
C18—H18	0.9300	Cl1—Cl3ⁱ	2.054 (8)
C19—C20	1.377 (2)	Cl2—Cl1ⁱ	0.952 (7)
C19—H19	0.9300	Cl2—C30ⁱ	1.512 (8)
C20—O3	1.3613 (19)	Cl2—Cl3ⁱ	1.871 (8)
C20—C21	1.406 (2)	Cl3—Cl2ⁱ	1.871 (8)
C21—O4	1.3577 (17)	Cl3—Cl1ⁱ	2.054 (8)
C21—C22	1.382 (2)	Cl3—C30ⁱ	2.065 (10)
C22—H22	0.9300

C3—C2—N1	108.14 (11)	C26—C25—H25	115.1
C3—C2—C16	127.64 (12)	C3—C25—H25	115.1
N1—C2—C16	123.93 (12)	C25—C26—C27	119.37 (13)
C2—C3—C4	108.30 (12)	C25—C26—H26	120.3
C2—C3—C25	129.64 (12)	C27—C26—H26	120.3
C4—C3—C25	122.05 (12)	O7—C27—O8	122.46 (15)
C5—C4—C9	119.96 (12)	O7—C27—C26	125.42 (15)
C5—C4—C3	132.26 (13)	O8—C27—C26	112.11 (13)
C9—C4—C3	107.78 (11)	O8—C28—C29	109.08 (17)
C6—C5—C4	118.49 (14)	O8—C28—H28A	109.9
C6—C5—H5	120.8	C29—C28—H28A	109.9
C4—C5—H5	120.8	O8—C28—H28B	109.9
C5—C6—C7	120.58 (13)	C29—C28—H28B	109.9
C5—C6—H6	119.7	H28A—C28—H28B	108.3
C7—C6—H6	119.7	C28—C29—H29A	109.5
C8—C7—C6	122.15 (14)	C28—C29—H29B	109.5
C8—C7—H7	118.9	H29A—C29—H29B	109.5
C6—C7—H7	118.9	C28—C29—H29C	109.5
C7—C8—C9	116.95 (14)	H29A—C29—H29C	109.5
C7—C8—H8	121.5	H29B—C29—H29C	109.5
C9—C8—H8	121.5	C2—N1—C9	108.64 (11)
C8—C9—C4	121.85 (13)	C2—N1—S1	128.29 (9)
C8—C9—N1	131.06 (13)	C9—N1—S1	122.44 (10)
C4—C9—N1	107.10 (11)	C20—O3—C23	116.43 (16)
C11—C10—C15	121.11 (18)	C21—O4—C24	117.78 (14)
C11—C10—S1	118.80 (13)	C27—O8—C28	115.21 (14)
C15—C10—S1	120.02 (16)	O1—S1—O2	120.63 (8)
C12—C11—C10	119.32 (19)	O1—S1—N1	106.73 (7)
C12—C11—H11	120.3	O2—S1—N1	105.65 (7)
C10—C11—H11	120.3	O1—S1—C10	108.29 (8)
C13—C12—C11	120.1 (2)	O2—S1—C10	108.90 (9)
C13—C12—H12	120.0	N1—S1—C10	105.65 (7)
C11—C12—H12	120.0	C30ⁱ—C30—Cl2ⁱ	71.5 (6)
C14—C13—C12	120.2 (2)	C30ⁱ—C30—Cl1ⁱ	70.3 (6)
C14—C13—H13	119.9	Cl2ⁱ—C30—Cl1ⁱ	128.4 (6)
C12—C13—H13	119.9	C30ⁱ—C30—Cl2	59.0 (5)
C13—C14—C15	121.2 (2)	Cl2ⁱ—C30—Cl2	130.5 (5)
C13—C14—H14	119.4	Cl1ⁱ—C30—Cl2	33.7 (3)
C15—C14—H14	119.4	C30ⁱ—C30—Cl1	62.0 (5)
C10—C15—C14	118.2 (2)	Cl2ⁱ—C30—Cl1	33.7 (3)
C10—C15—H15	120.9	Cl1ⁱ—C30—Cl1	132.3 (4)
C14—C15—H15	120.9	Cl2—C30—Cl1	112.0 (4)
C2—C16—C17	115.26 (11)	C30ⁱ—C30—Cl3	79.2 (7)
C2—C16—H16A	108.5	Cl2ⁱ—C30—Cl3	67.0 (4)
C17—C16—H16A	108.5	Cl1ⁱ—C30—Cl3	72.9 (4)
C2—C16—H16B	108.5	Cl2—C30—Cl3	101.7 (5)
C17—C16—H16B	108.5	Cl1—C30—Cl3	97.4 (4)
H16A—C16—H16B	107.5	C30ⁱ—C30—Cl3ⁱ	61.2 (6)
C18—C17—C22	118.73 (13)	Cl2ⁱ—C30—Cl3ⁱ	98.2 (4)
C18—C17—C16	121.92 (12)	Cl1ⁱ—C30—Cl3ⁱ	92.5 (4)
C22—C17—C16	119.34 (12)	Cl2—C30—Cl3ⁱ	59.0 (4)
C17—C18—C19	120.84 (13)	Cl1—C30—Cl3ⁱ	65.2 (3)
C17—C18—H18	119.6	Cl3—C30—Cl3ⁱ	140.4 (4)
C19—C18—H18	119.6	C30ⁱ—C30—H30A	166.2
C20—C19—C18	120.44 (14)	Cl2ⁱ—C30—H30A	113.6
C20—C19—H19	119.8	Cl1ⁱ—C30—H30A	111.7
C18—C19—H19	119.8	Cl2—C30—H30A	114.6
O3—C20—C19	125.06 (15)	Cl1—C30—H30A	114.5
O3—C20—C21	115.52 (13)	Cl3—C30—H30A	114.6
C19—C20—C21	119.42 (13)	Cl3ⁱ—C30—H30A	105.0
O4—C21—C22	125.01 (14)	Cl2ⁱ—Cl1—C30ⁱ	77.3 (4)
O4—C21—C20	115.26 (13)	Cl2ⁱ—Cl1—C30	61.8 (5)
C22—C21—C20	119.73 (13)	C30ⁱ—Cl1—C30	47.7 (4)
C21—C22—C17	120.79 (13)	Cl2ⁱ—Cl1—Cl3ⁱ	126.3 (5)
C21—C22—H22	119.6	C30ⁱ—Cl1—Cl3ⁱ	59.0 (4)
C17—C22—H22	119.6	C30—Cl1—Cl3ⁱ	65.8 (3)
O3—C23—H23A	109.5	Cl1ⁱ—Cl2—C30ⁱ	84.5 (6)
O3—C23—H23B	109.5	Cl1ⁱ—Cl2—C30	69.0 (5)
H23A—C23—H23B	109.5	C30ⁱ—Cl2—C30	49.5 (5)
O3—C23—H23C	109.5	Cl1ⁱ—Cl2—Cl3ⁱ	139.6 (5)
H23A—C23—H23C	109.5	C30ⁱ—Cl2—Cl3ⁱ	65.0 (4)
H23B—C23—H23C	109.5	C30—Cl2—Cl3ⁱ	71.0 (4)
O4—C24—H24A	109.5	C30—Cl3—Cl2ⁱ	48.0 (3)
O4—C24—H24B	109.5	C30—Cl3—Cl1ⁱ	48.2 (3)
H24A—C24—H24B	109.5	Cl2ⁱ—Cl3—Cl1ⁱ	91.0 (3)
O4—C24—H24C	109.5	C30—Cl3—C30ⁱ	39.6 (4)
H24A—C24—H24C	109.5	Cl2ⁱ—Cl3—C30ⁱ	50.0 (2)
H24B—C24—H24C	109.5	Cl1ⁱ—Cl3—C30ⁱ	49.0 (2)
C26—C25—C3	129.71 (14)

N1—C2—C3—C4	0.77 (15)	O7—C27—O8—C28	−1.2 (3)
C16—C2—C3—C4	−173.17 (13)	C26—C27—O8—C28	179.76 (18)
N1—C2—C3—C25	179.76 (14)	C29—C28—O8—C27	179.7 (2)
C16—C2—C3—C25	5.8 (2)	C2—N1—S1—O1	21.70 (15)
C2—C3—C4—C5	178.86 (15)	C9—N1—S1—O1	−168.44 (11)
C25—C3—C4—C5	−0.2 (2)	C2—N1—S1—O2	151.24 (13)
C2—C3—C4—C9	−1.78 (15)	C9—N1—S1—O2	−38.90 (14)
C25—C3—C4—C9	179.13 (13)	C2—N1—S1—C10	−93.43 (13)
C9—C4—C5—C6	−1.5 (2)	C9—N1—S1—C10	76.43 (13)
C3—C4—C5—C6	177.80 (15)	C11—C10—S1—O1	−25.83 (15)
C4—C5—C6—C7	0.1 (2)	C15—C10—S1—O1	151.37 (15)
C5—C6—C7—C8	1.2 (3)	C11—C10—S1—O2	−158.70 (13)
C6—C7—C8—C9	−1.0 (2)	C15—C10—S1—O2	18.50 (18)
C7—C8—C9—C4	−0.4 (2)	C11—C10—S1—N1	88.22 (14)
C7—C8—C9—N1	179.80 (15)	C15—C10—S1—N1	−94.58 (16)
C5—C4—C9—C8	1.7 (2)	C30ⁱ—C30—Cl1—Cl2ⁱ	98.6 (8)
C3—C4—C9—C8	−177.79 (13)	Cl1ⁱ—C30—Cl1—Cl2ⁱ	98.6 (8)
C5—C4—C9—N1	−178.49 (12)	Cl2—C30—Cl1—Cl2ⁱ	131.0 (6)
C3—C4—C9—N1	2.06 (15)	Cl3—C30—Cl1—Cl2ⁱ	25.1 (6)
C15—C10—C11—C12	−0.1 (3)	Cl3ⁱ—C30—Cl1—Cl2ⁱ	167.8 (7)
S1—C10—C11—C12	177.03 (15)	Cl2ⁱ—C30—Cl1—C30ⁱ	−98.6 (8)
C10—C11—C12—C13	0.3 (3)	Cl1ⁱ—C30—Cl1—C30ⁱ	0.0
C11—C12—C13—C14	−0.4 (4)	Cl2—C30—Cl1—C30ⁱ	32.3 (5)
C12—C13—C14—C15	0.3 (5)	Cl3—C30—Cl1—C30ⁱ	−73.5 (6)
C11—C10—C15—C14	0.1 (3)	Cl3ⁱ—C30—Cl1—C30ⁱ	69.2 (6)
S1—C10—C15—C14	−177.1 (2)	C30ⁱ—C30—Cl1—Cl3ⁱ	−69.2 (6)
C13—C14—C15—C10	−0.2 (4)	Cl2ⁱ—C30—Cl1—Cl3ⁱ	−167.8 (7)
C3—C2—C16—C17	−103.22 (16)	Cl1ⁱ—C30—Cl1—Cl3ⁱ	−69.2 (6)
N1—C2—C16—C17	83.73 (16)	Cl2—C30—Cl1—Cl3ⁱ	−36.8 (5)
C2—C16—C17—C18	40.18 (19)	Cl3—C30—Cl1—Cl3ⁱ	−142.7 (4)
C2—C16—C17—C22	−141.19 (13)	C30ⁱ—C30—Cl2—Cl1ⁱ	−101.1 (8)
C22—C17—C18—C19	−1.8 (2)	Cl2ⁱ—C30—Cl2—Cl1ⁱ	−101.1 (8)
C16—C17—C18—C19	176.82 (13)	Cl1—C30—Cl2—Cl1ⁱ	−134.6 (6)
C17—C18—C19—C20	0.4 (2)	Cl3—C30—Cl2—Cl1ⁱ	−31.5 (6)
C18—C19—C20—O3	−177.63 (16)	Cl3ⁱ—C30—Cl2—Cl1ⁱ	−174.0 (7)
C18—C19—C20—C21	1.8 (2)	Cl2ⁱ—C30—Cl2—C30ⁱ	0.0
O3—C20—C21—O4	−2.2 (2)	Cl1ⁱ—C30—Cl2—C30ⁱ	101.1 (8)
C19—C20—C21—O4	178.36 (15)	Cl1—C30—Cl2—C30ⁱ	−33.4 (4)
O3—C20—C21—C22	176.88 (15)	Cl3—C30—Cl2—C30ⁱ	69.6 (6)
C19—C20—C21—C22	−2.6 (2)	Cl3ⁱ—C30—Cl2—C30ⁱ	−72.9 (6)
O4—C21—C22—C17	−179.85 (14)	C30ⁱ—C30—Cl2—Cl3ⁱ	72.9 (6)
C20—C21—C22—C17	1.2 (2)	Cl2ⁱ—C30—Cl2—Cl3ⁱ	72.9 (6)
C18—C17—C22—C21	1.0 (2)	Cl1ⁱ—C30—Cl2—Cl3ⁱ	174.0 (7)
C16—C17—C22—C21	−177.68 (13)	Cl1—C30—Cl2—Cl3ⁱ	39.4 (5)
C2—C3—C25—C26	26.6 (3)	Cl3—C30—Cl2—Cl3ⁱ	142.5 (4)
C4—C3—C25—C26	−154.55 (16)	C30ⁱ—C30—Cl3—Cl2ⁱ	−74.4 (5)
C3—C25—C26—C27	175.66 (15)	Cl1ⁱ—C30—Cl3—Cl2ⁱ	−146.9 (5)
C25—C26—C27—O7	1.8 (3)	Cl2—C30—Cl3—Cl2ⁱ	−129.3 (5)
C25—C26—C27—O8	−179.10 (16)	Cl1—C30—Cl3—Cl2ⁱ	−14.8 (3)
C3—C2—N1—C9	0.52 (15)	Cl3ⁱ—C30—Cl3—Cl2ⁱ	−74.4 (5)
C16—C2—N1—C9	174.73 (12)	C30ⁱ—C30—Cl3—Cl1ⁱ	72.6 (5)
C3—C2—N1—S1	171.49 (10)	Cl2ⁱ—C30—Cl3—Cl1ⁱ	146.9 (5)
C16—C2—N1—S1	−14.3 (2)	Cl2—C30—Cl3—Cl1ⁱ	17.7 (3)
C8—C9—N1—C2	178.21 (15)	Cl1—C30—Cl3—Cl1ⁱ	132.1 (4)
C4—C9—N1—C2	−1.62 (15)	Cl3ⁱ—C30—Cl3—Cl1ⁱ	72.6 (5)
C8—C9—N1—S1	6.6 (2)	Cl2ⁱ—C30—Cl3—C30ⁱ	74.4 (5)
C4—C9—N1—S1	−173.23 (10)	Cl1ⁱ—C30—Cl3—C30ⁱ	−72.6 (5)
C19—C20—O3—C23	7.7 (3)	Cl2—C30—Cl3—C30ⁱ	−54.9 (5)
C21—C20—O3—C23	−171.8 (2)	Cl1—C30—Cl3—C30ⁱ	59.5 (5)
C22—C21—O4—C24	4.9 (3)	Cl3ⁱ—C30—Cl3—C30ⁱ	0.000 (1)
C20—C21—O4—C24	−176.06 (18)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2	0.93	2.38	2.928 (2)	118
C15—H15···O4ⁱⁱ	0.93	2.53	3.411 (3)	159
C16—H16A···O1	0.97	2.30	2.831 (2)	114
C24—H24B···O7ⁱⁱⁱ	0.96	2.51	3.461 (2)	169
C24—H24A···O7^iv	0.96	2.52	3.367 (3)	147
C25—H25···O7	0.93	2.46	2.821 (2)	103
C30—H30A···O3^v	0.96	2.59	3.429 (7)	146
C30—H30A···O4^v	0.96	2.55	3.424 (7)	151

Symmetry codes: (ii) x+1, y, z; (iii) x−1, y, z+1; (iv) −x+1, −y+1, −z; (v) x+1, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₇NO₆S·0.5CHCl₃
M_r	565.25
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.2154 (3), 12.0504 (4), 12.6310 (4)
α, β, γ (°)	70.602 (2), 69.613 (1), 77.056 (2)
V (Å³)	1364.39 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.913, 0.941
No. of measured, independent and observed [I > 2σ(I)] reflections	38797, 10612, 7709
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.794

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.189, 1.04
No. of reflections	10612
No. of parameters	364
No. of restraints	27
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.46

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2	0.93	2.38	2.928 (2)	118
C15—H15···O4ⁱ	0.93	2.53	3.411 (3)	159
C16—H16A···O1	0.97	2.30	2.831 (2)	114
C24—H24B···O7ⁱⁱ	0.96	2.51	3.461 (2)	169
C24—H24A···O7ⁱⁱⁱ	0.96	2.52	3.367 (3)	147
C25—H25···O7	0.93	2.46	2.821 (2)	103
C30—H30A···O3^iv	0.96	2.59	3.429 (7)	146
C30—H30A···O4^iv	0.96	2.55	3.424 (7)	151

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

Acknowledgements

MT thanks the UGC for financial support in the form of a Research Fellowship in Science for Meritorious Students.

References

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 3-[2-(3,4-dimeth­­oxy­benz­yl)-1-phenyl­sulfonyl-1H-indol-3-yl]acrylate chloro­form hemisolvate

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Experimental

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Data collection

Refinement

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Acknowledgements

References

organic compounds

Ethyl 3-[2-(3,4-dimethoxybenzyl)-1-phenylsulfonyl-1H-indol-3-yl]acrylate chloroform hemisolvate