Diethyl 2-[(5-meth­oxy-2-methyl-1-phenyl­sulfonyl-1H-indol-3-yl)methyl­ene]malonate

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

doi:10.1107/S1600536809019369

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Pages o1418-o1419

doi:10.1107/S1600536809019369

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Diethyl 2-[(5-methoxy-2-methyl-1-phenylsulfonyl-1H-indol-3-yl)methylene]malonate

T. Kavitha,^a M. Thenmozhi,^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 31 March 2009; accepted 21 May 2009; online 29 May 2009)

In the title compound, C₂₄H₂₅NO₇S, the sulfonyl-bound phenyl ring is approximately perpendicular to the indole ring system [dihedral angle = 87.72 (5)°]. The methyl group of one of the ester units is disordered over two positions with occupancies of 0.527 (13) and 0.473 (13). An intramolecular C—H⋯O hydrogen bond is observed. In the crystal structure, molecules are linked into a ribbon structure running along the c axis by intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions involving the pyrrole ring.

Related literature

For general background on indoles, see: El-Sayed et al. (1986 ); Farhanullah et al. (2004 ); Okabe & Adachi (1998 ); Schollmeyer et al. (1995 ). For the Thorpe–Ingold effect, see: Bassindale (1984 ). For hybridization, see: Beddoes et al. (1986 ). For a related structure, see: Chakkaravarthi et al. (2008 ).

Experimental

Crystal data

C₂₄H₂₅NO₇S
M_r = 471.51
Triclinic, $[P \overline 1]$
a = 8.7597 (2) Å
b = 10.9029 (2) Å
c = 12.5186 (3) Å
α = 88.402 (1)°
β = 79.723 (1)°
γ = 83.635 (2)°
V = 1169.13 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 293 K
0.22 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.964, T_max = 0.971
27454 measured reflections
6218 independent reflections
4628 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.176
S = 1.07
6218 reflections
309 parameters
16 restraints
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C2–C5 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1	0.93	2.32	2.901 (3)	120
C14—H14⋯O5ⁱ	0.93	2.42	3.349 (3)	173
C25—H25C⋯Cg1ⁱⁱ	0.96	2.92	3.515 (3)	140
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y+1, -z+1.

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, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019369/ci2774sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019369/ci2774Isup2.hkl

checkCIF report

Comment top

Indoles form an integral part of many natural products and possess potentially reactive sites to perform variety of chemical reactions to generate molecular diversity (Farhanullah et al., 2004). Many of the indole derivatives are found to possess antibacterial (Okabe & Adachi, 1998), antitumour (Schollmeyer et al., 1995) and antimicrobial (El-Sayed et al., 1986) activities.

The bond angles around atom S1 show significant deviation from regular tetrahedral geometry. The widening of O1—S1—O2 [120.42 (11)°] and the narrowing of the angle N1—S1—C10 [104.43 (9)°] are attributed to the Thorpe-Ingold effect (Bassindale, 1984). The indole ring system is planar. The bond lengths and angles are comparable to those observed in a related structure (Chakkaravarthi et al., 2008). The sum of bond angles around atom N1 (357.9°) indicates that the atom N1 is in sp² hybridized state (Beddoes et al., 1986). The sulfonyl bound phenyl ring (C10–C15) is approximately perpendicular to the indole ring system, with the dihedral angle being 87.72 (5)°. The C18–C21/O3/O4 ester group shows an extended conformation, as is evident from the torsion angles C18—C19—O4—C20 = 179.8 (2)° and C19—O4—C20—C21 = -169.9 (3)°. The terminal methyl group of the other ester group is disordered over two positions. An intramolecular C6—H6···O1 hydrogen bond is observed.

In the crystal structure, the molecules are linked into a zigzag C(12) chain running along the c axis by intermolecular C—H···O hydrogen bonds involving atoms C14 and O5 (Table 1). The inversion-related molecules of adjacent chains are linked via weak C—H···π interactions involving the N1/C2–C5 ring (centroid Cg1) to form a ribbon structure (Fig. 2).

Related literature top

For general background on indoles, see: El-Sayed et al. (1986); Farhanullah et al. (2004); Okabe & Adachi (1998); Schollmeyer et al. (1995). For the Thorpe–Ingold effect, see: Bassindale (1984). For hybridization, see: Beddoes et al. (1986). For a related structure, see: Chakkaravarthi et al. (2008).

Experimental top

A solution of TiCl₄ (0.37 ml, 3.34 mmol) in dry dichloromethane (DCM; 20 ml) was added drop by drop into dry DCM (10 ml) kept at 273 K and stirred at the same temperature for 45 min. To this, a solution of 5-methoxy-2-methyl-1-(phenylsulfonyl)-1H-indole-3-carbaldehyde (0.5 g, 1.52 mmol) and diethylmalonate (0.24 ml, 1.60 mmol) in dry DCM (20 ml) was slowly added. After the addition was completed, the reaction mixture was stirred at 273 K for 1 h. A solution of pyridine (0.6 ml, 6.08 mmol) in dry DCM (20 ml) was then added dropwise for 30 min. The content was stirred at 273 K for 12 h and then at room temperature for 48 h. The reaction mass was quenched with water and extracted with CHCl₃ (2 × 10 ml). The organic layer was washed with 0.5 M HCl (2 × 20 ml) followed by brine solution (2 × 20 ml). Removal of solvent followed by flash column chromatographic purification (n-hexane–ethyl acetate 97:3) afforded the title compound as a yellow solid. Single crystals were obtained by recrystallizing the compound from n-hexane–ethyl acetate (97:3).

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, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 20% probability level. H atoms have been omitted for clarity. Both disorder components are shown.
	Fig. 2. Crystal packing of the title compound. H atoms not involved in hydrogen bonding (dashed lines) have been omitted.

Diethyl 2-[(5-methoxy-2-methyl-1-phenylsulfonyl-1H-indol-3-yl)methylene]malonate top

Crystal data top

C₂₄H₂₅NO₇S	Z = 2
M_r = 471.51	F(000) = 496
Triclinic, P1	D_x = 1.339 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7597 (2) Å	Cell parameters from 6218 reflections
b = 10.9029 (2) Å	θ = 1.6–29.1°
c = 12.5186 (3) Å	µ = 0.18 mm⁻¹
α = 88.402 (1)°	T = 293 K
β = 79.723 (1)°	Block, yellow
γ = 83.635 (2)°	0.22 × 0.18 × 0.15 mm
V = 1169.13 (4) Å³

Data collection top

Bruker Kappa-APEXII area-detector diffractometer	6218 independent reflections
Radiation source: fine-focus sealed tube	4628 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω and ϕ scans	θ_max = 29.1°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −11→11
T_min = 0.964, T_max = 0.971	k = −14→14
27454 measured reflections	l = −17→17

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.09P)² + 0.3748P] where P = (F_o² + 2F_c²)/3
6218 reflections	(Δ/σ)_max = 0.001
309 parameters	Δρ_max = 0.66 e Å⁻³
16 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₂₄H₂₅NO₇S	γ = 83.635 (2)°
M_r = 471.51	V = 1169.13 (4) Å³
Triclinic, P1	Z = 2
a = 8.7597 (2) Å	Mo Kα radiation
b = 10.9029 (2) Å	µ = 0.18 mm⁻¹
c = 12.5186 (3) Å	T = 293 K
α = 88.402 (1)°	0.22 × 0.18 × 0.15 mm
β = 79.723 (1)°

Data collection top

Bruker Kappa-APEXII area-detector diffractometer	6218 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	4628 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.971	R_int = 0.023
27454 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	16 restraints
wR(F²) = 0.176	H-atom parameters constrained
S = 1.07	Δρ_max = 0.66 e Å⁻³
6218 reflections	Δρ_min = −0.45 e Å⁻³
309 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	0.1929 (2)	0.26604 (18)	0.44185 (16)	0.0459 (4)
C3	0.2837 (2)	0.35252 (17)	0.39343 (15)	0.0423 (4)
C4	0.2631 (2)	0.45572 (17)	0.46608 (14)	0.0390 (4)
C5	0.1556 (2)	0.43026 (17)	0.55745 (15)	0.0399 (4)
C6	0.1105 (2)	0.51428 (18)	0.64167 (15)	0.0462 (4)
H6	0.0372	0.4979	0.7023	0.055*
C7	0.1787 (2)	0.62274 (19)	0.63165 (16)	0.0482 (4)
H7	0.1523	0.6797	0.6876	0.058*
C8	0.2861 (2)	0.64990 (18)	0.54028 (16)	0.0442 (4)
C9	0.3283 (2)	0.56763 (18)	0.45571 (15)	0.0427 (4)
H9	0.3979	0.5861	0.3937	0.051*
C10	0.1592 (2)	0.15262 (18)	0.70459 (16)	0.0461 (4)
C11	0.2091 (3)	0.0301 (2)	0.68271 (18)	0.0550 (5)
H11	0.1655	−0.0122	0.6342	0.066*
C12	0.3239 (3)	−0.0290 (2)	0.7332 (2)	0.0682 (6)
H12	0.3584	−0.1117	0.7190	0.082*
C13	0.3875 (3)	0.0341 (3)	0.8045 (2)	0.0745 (7)
H13	0.4654	−0.0061	0.8384	0.089*
C14	0.3377 (4)	0.1551 (3)	0.8262 (2)	0.0756 (7)
H14	0.3818	0.1968	0.8749	0.091*
C15	0.2218 (3)	0.2167 (2)	0.77638 (19)	0.0611 (6)
H15	0.1873	0.2993	0.7911	0.073*
C16	0.1853 (4)	0.1390 (2)	0.4038 (2)	0.0672 (6)
H16A	0.0883	0.1354	0.3790	0.101*
H16B	0.1924	0.0813	0.4625	0.101*
H16C	0.2704	0.1183	0.3452	0.101*
C17	0.3945 (2)	0.34685 (18)	0.29260 (16)	0.0465 (4)
H17	0.4866	0.3808	0.2952	0.056*
C18	0.3860 (2)	0.30077 (18)	0.19641 (16)	0.0470 (4)
C19	0.2432 (2)	0.2538 (2)	0.17047 (16)	0.0506 (5)
C20	0.1390 (3)	0.0829 (3)	0.1115 (3)	0.0788 (8)
H20A	0.1112	0.1196	0.0452	0.095*
H20B	0.0494	0.0975	0.1693	0.095*
C21	0.1827 (5)	−0.0488 (3)	0.0973 (3)	0.1081 (12)
H21A	0.0969	−0.0865	0.0789	0.162*
H21B	0.2087	−0.0846	0.1636	0.162*
H21C	0.2714	−0.0625	0.0400	0.162*
C22	0.5148 (3)	0.3041 (2)	0.10308 (19)	0.0587 (5)
C23	0.7754 (4)	0.3516 (4)	0.0435 (3)	0.1053 (13)
H23A	0.7917	0.2818	−0.0051	0.126*
H23B	0.8686	0.3537	0.0748	0.126*
C24	0.7462 (13)	0.4658 (8)	−0.0169 (9)	0.136 (4)	0.527 (13)
H24A	0.8345	0.4753	−0.0730	0.204*	0.527 (13)
H24B	0.7299	0.5346	0.0315	0.204*	0.527 (13)
H24C	0.6551	0.4626	−0.0491	0.204*	0.527 (13)
C24'	0.8132 (13)	0.4810 (6)	0.0454 (10)	0.125 (4)	0.473 (13)
H24D	0.9014	0.4925	−0.0102	0.187*	0.473 (13)
H24E	0.8375	0.4977	0.1150	0.187*	0.473 (13)
H24F	0.7251	0.5364	0.0326	0.187*	0.473 (13)
C25	0.4367 (3)	0.8015 (2)	0.4473 (2)	0.0655 (6)
H25A	0.4678	0.8809	0.4593	0.098*
H25B	0.3789	0.8073	0.3887	0.098*
H25C	0.5277	0.7433	0.4291	0.098*
N1	0.10926 (19)	0.31258 (15)	0.54194 (13)	0.0450 (4)
O1	−0.07993 (18)	0.31630 (15)	0.71397 (14)	0.0640 (4)
O2	−0.05720 (19)	0.14123 (16)	0.59054 (15)	0.0668 (5)
O3	0.11914 (19)	0.31388 (18)	0.17716 (15)	0.0703 (5)
O4	0.27014 (18)	0.13750 (15)	0.13834 (14)	0.0620 (4)
O5	0.5020 (3)	0.2806 (3)	0.01285 (16)	0.1019 (8)
O6	0.6431 (2)	0.3383 (2)	0.12855 (16)	0.0883 (7)
O7	0.34224 (19)	0.76187 (14)	0.54229 (13)	0.0588 (4)
S1	0.01286 (6)	0.23002 (5)	0.64069 (4)	0.04951 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0544 (10)	0.0432 (10)	0.0434 (9)	−0.0068 (8)	−0.0163 (8)	0.0002 (8)
C3	0.0455 (9)	0.0434 (9)	0.0398 (9)	−0.0034 (7)	−0.0130 (7)	−0.0031 (7)
C4	0.0372 (8)	0.0437 (9)	0.0376 (8)	−0.0026 (7)	−0.0115 (7)	−0.0017 (7)
C5	0.0388 (8)	0.0407 (9)	0.0412 (9)	−0.0036 (7)	−0.0111 (7)	0.0038 (7)
C6	0.0467 (10)	0.0499 (10)	0.0397 (9)	−0.0027 (8)	−0.0031 (7)	0.0012 (8)
C7	0.0522 (10)	0.0478 (10)	0.0436 (10)	−0.0023 (8)	−0.0064 (8)	−0.0076 (8)
C8	0.0439 (9)	0.0434 (10)	0.0473 (10)	−0.0062 (7)	−0.0128 (8)	−0.0022 (8)
C9	0.0397 (8)	0.0478 (10)	0.0414 (9)	−0.0075 (7)	−0.0079 (7)	−0.0001 (7)
C10	0.0471 (9)	0.0492 (10)	0.0428 (9)	−0.0094 (8)	−0.0088 (8)	0.0095 (8)
C11	0.0635 (12)	0.0507 (11)	0.0528 (11)	−0.0101 (9)	−0.0147 (10)	0.0068 (9)
C12	0.0740 (15)	0.0624 (14)	0.0659 (15)	0.0076 (12)	−0.0171 (12)	0.0075 (12)
C13	0.0711 (15)	0.0868 (14)	0.0675 (15)	0.0054 (13)	−0.0279 (13)	0.0119 (13)
C14	0.0849 (18)	0.0880 (15)	0.0622 (14)	−0.0091 (14)	−0.0347 (14)	−0.0049 (13)
C15	0.0748 (15)	0.0584 (13)	0.0537 (12)	−0.0061 (11)	−0.0216 (11)	−0.0009 (10)
C16	0.1018 (19)	0.0461 (11)	0.0566 (13)	−0.0175 (12)	−0.0155 (13)	−0.0015 (10)
C17	0.0470 (10)	0.0458 (10)	0.0471 (10)	−0.0044 (8)	−0.0089 (8)	−0.0051 (8)
C18	0.0461 (10)	0.0489 (10)	0.0460 (10)	−0.0036 (8)	−0.0078 (8)	−0.0071 (8)
C19	0.0474 (10)	0.0630 (12)	0.0409 (9)	−0.0042 (9)	−0.0062 (8)	−0.0079 (9)
C20	0.0690 (16)	0.093 (2)	0.0817 (18)	−0.0299 (14)	−0.0183 (13)	−0.0193 (15)
C21	0.112 (3)	0.092 (2)	0.126 (3)	−0.050 (2)	−0.008 (2)	−0.026 (2)
C22	0.0522 (11)	0.0685 (14)	0.0543 (12)	−0.0114 (10)	−0.0009 (9)	−0.0172 (10)
C23	0.0772 (19)	0.128 (3)	0.105 (2)	−0.044 (2)	0.0246 (15)	−0.035 (2)
C24	0.135 (4)	0.136 (4)	0.136 (4)	−0.0144 (11)	−0.0234 (12)	0.0001 (10)
C24'	0.125 (4)	0.125 (4)	0.125 (4)	−0.0152 (11)	−0.0213 (12)	0.0003 (10)
C25	0.0642 (14)	0.0622 (14)	0.0728 (15)	−0.0255 (11)	−0.0089 (11)	0.0043 (11)
N1	0.0512 (9)	0.0430 (8)	0.0429 (8)	−0.0096 (7)	−0.0122 (7)	0.0052 (6)
O1	0.0498 (8)	0.0646 (10)	0.0700 (10)	−0.0029 (7)	0.0056 (7)	0.0129 (8)
O2	0.0590 (9)	0.0645 (10)	0.0867 (12)	−0.0265 (8)	−0.0296 (8)	0.0149 (9)
O3	0.0480 (8)	0.0871 (12)	0.0744 (11)	0.0051 (8)	−0.0117 (8)	−0.0208 (9)
O4	0.0545 (8)	0.0616 (9)	0.0736 (10)	−0.0097 (7)	−0.0169 (7)	−0.0169 (8)
O5	0.0799 (13)	0.169 (2)	0.0583 (11)	−0.0429 (14)	0.0093 (9)	−0.0447 (13)
O6	0.0620 (11)	0.1307 (18)	0.0742 (12)	−0.0402 (11)	0.0049 (8)	−0.0285 (12)
O7	0.0675 (9)	0.0513 (8)	0.0599 (9)	−0.0203 (7)	−0.0080 (7)	−0.0071 (7)
S1	0.0422 (3)	0.0513 (3)	0.0567 (3)	−0.0116 (2)	−0.0114 (2)	0.0123 (2)

Geometric parameters (Å, º) top

C2—C3	1.360 (3)	C17—H17	0.93
C2—N1	1.411 (3)	C18—C22	1.475 (3)
C2—C16	1.490 (3)	C18—C19	1.493 (3)
C3—C4	1.442 (2)	C19—O3	1.196 (3)
C3—C17	1.447 (3)	C19—O4	1.324 (3)
C4—C5	1.388 (3)	C20—O4	1.445 (3)
C4—C9	1.396 (3)	C20—C21	1.452 (5)
C5—C6	1.390 (3)	C20—H20A	0.97
C5—N1	1.416 (2)	C20—H20B	0.97
C6—C7	1.376 (3)	C21—H21A	0.96
C6—H6	0.93	C21—H21B	0.96
C7—C8	1.393 (3)	C21—H21C	0.96
C7—H7	0.93	C22—O5	1.193 (3)
C8—O7	1.368 (2)	C22—O6	1.316 (3)
C8—C9	1.379 (3)	C23—O6	1.445 (3)
C9—H9	0.93	C23—C24	1.461 (5)
C10—C15	1.376 (3)	C23—C24'	1.486 (5)
C10—C11	1.378 (3)	C23—H23A	0.97
C10—S1	1.756 (2)	C23—H23B	0.97
C11—C12	1.373 (3)	C24—H24A	0.96
C11—H11	0.93	C24—H24B	0.96
C12—C13	1.370 (4)	C24—H24C	0.96
C12—H12	0.93	C24'—H24D	0.96
C13—C14	1.362 (4)	C24'—H24E	0.96
C13—H13	0.93	C24'—H24F	0.96
C14—C15	1.386 (3)	C25—O7	1.409 (3)
C14—H14	0.93	C25—H25A	0.96
C15—H15	0.93	C25—H25B	0.96
C16—H16A	0.96	C25—H25C	0.96
C16—H16B	0.96	N1—S1	1.6690 (16)
C16—H16C	0.96	O1—S1	1.4141 (17)
C17—C18	1.335 (3)	O2—S1	1.4181 (17)

C3—C2—N1	108.67 (16)	O4—C19—C18	111.98 (17)
C3—C2—C16	128.0 (2)	O4—C20—C21	108.4 (3)
N1—C2—C16	123.20 (19)	O4—C20—H20A	110.0
C2—C3—C4	107.82 (17)	C21—C20—H20A	110.0
C2—C3—C17	129.75 (18)	O4—C20—H20B	110.0
C4—C3—C17	122.24 (17)	C21—C20—H20B	110.0
C5—C4—C9	120.75 (17)	H20A—C20—H20B	108.4
C5—C4—C3	108.18 (16)	C20—C21—H21A	109.5
C9—C4—C3	131.05 (17)	C20—C21—H21B	109.5
C4—C5—C6	121.34 (17)	H21A—C21—H21B	109.5
C4—C5—N1	106.95 (16)	C20—C21—H21C	109.5
C6—C5—N1	131.70 (17)	H21A—C21—H21C	109.5
C7—C6—C5	117.28 (18)	H21B—C21—H21C	109.5
C7—C6—H6	121.4	O5—C22—O6	123.5 (2)
C5—C6—H6	121.4	O5—C22—C18	122.8 (2)
C6—C7—C8	122.06 (18)	O6—C22—C18	113.66 (19)
C6—C7—H7	119.0	O6—C23—C24	109.3 (5)
C8—C7—H7	119.0	O6—C23—C24'	107.6 (5)
O7—C8—C9	124.44 (18)	O6—C23—H23A	109.8
O7—C8—C7	114.95 (17)	C24—C23—H23A	109.8
C9—C8—C7	120.60 (18)	C24'—C23—H23A	140.2
C8—C9—C4	117.94 (17)	O6—C23—H23B	109.8
C8—C9—H9	121.0	C24—C23—H23B	109.8
C4—C9—H9	121.0	C24'—C23—H23B	70.5
C15—C10—C11	121.2 (2)	H23A—C23—H23B	108.3
C15—C10—S1	118.66 (17)	C23—C24—H24A	109.5
C11—C10—S1	120.13 (16)	C23—C24—H24B	109.5
C12—C11—C10	119.4 (2)	H24A—C24—H24B	109.5
C12—C11—H11	120.3	C23—C24—H24C	109.5
C10—C11—H11	120.3	H24A—C24—H24C	109.5
C13—C12—C11	119.9 (2)	H24B—C24—H24C	109.5
C13—C12—H12	120.1	C23—C24'—H24D	109.5
C11—C12—H12	120.1	C23—C24'—H24E	109.5
C14—C13—C12	120.7 (2)	H24D—C24'—H24E	109.5
C14—C13—H13	119.7	C23—C24'—H24F	109.5
C12—C13—H13	119.7	H24D—C24'—H24F	109.5
C13—C14—C15	120.5 (2)	H24E—C24'—H24F	109.5
C13—C14—H14	119.7	O7—C25—H25A	109.5
C15—C14—H14	119.7	O7—C25—H25B	109.5
C10—C15—C14	118.3 (2)	H25A—C25—H25B	109.5
C10—C15—H15	120.8	O7—C25—H25C	109.5
C14—C15—H15	120.8	H25A—C25—H25C	109.5
C2—C16—H16A	109.5	H25B—C25—H25C	109.5
C2—C16—H16B	109.5	C2—N1—C5	108.32 (15)
H16A—C16—H16B	109.5	C2—N1—S1	125.65 (13)
C2—C16—H16C	109.5	C5—N1—S1	123.91 (13)
H16A—C16—H16C	109.5	C19—O4—C20	116.42 (19)
H16B—C16—H16C	109.5	C22—O6—C23	119.1 (2)
C18—C17—C3	130.42 (19)	C8—O7—C25	117.79 (17)
C18—C17—H17	114.8	O1—S1—O2	120.42 (11)
C3—C17—H17	114.8	O1—S1—N1	106.20 (9)
C17—C18—C22	121.49 (19)	O2—S1—N1	107.38 (10)
C17—C18—C19	123.87 (18)	O1—S1—C10	108.77 (10)
C22—C18—C19	114.37 (17)	O2—S1—C10	108.50 (10)
O3—C19—O4	123.8 (2)	N1—S1—C10	104.43 (9)
O3—C19—C18	124.2 (2)

N1—C2—C3—C4	2.4 (2)	C17—C18—C19—O4	−122.7 (2)
C16—C2—C3—C4	−173.8 (2)	C22—C18—C19—O4	63.2 (2)
N1—C2—C3—C17	177.27 (18)	C17—C18—C22—O5	−168.7 (3)
C16—C2—C3—C17	1.0 (3)	C19—C18—C22—O5	5.6 (4)
C2—C3—C4—C5	−1.4 (2)	C17—C18—C22—O6	9.7 (3)
C17—C3—C4—C5	−176.76 (16)	C19—C18—C22—O6	−176.0 (2)
C2—C3—C4—C9	−179.75 (18)	C3—C2—N1—C5	−2.5 (2)
C17—C3—C4—C9	4.9 (3)	C16—C2—N1—C5	173.94 (19)
C9—C4—C5—C6	−0.6 (3)	C3—C2—N1—S1	−166.42 (13)
C3—C4—C5—C6	−179.14 (16)	C16—C2—N1—S1	10.0 (3)
C9—C4—C5—N1	178.41 (15)	C4—C5—N1—C2	1.58 (19)
C3—C4—C5—N1	−0.13 (19)	C6—C5—N1—C2	−179.56 (19)
C4—C5—C6—C7	−1.1 (3)	C4—C5—N1—S1	165.83 (13)
N1—C5—C6—C7	−179.83 (18)	C6—C5—N1—S1	−15.3 (3)
C5—C6—C7—C8	1.4 (3)	O3—C19—O4—C20	−0.6 (3)
C6—C7—C8—O7	179.45 (18)	C18—C19—O4—C20	179.8 (2)
C6—C7—C8—C9	0.0 (3)	C21—C20—O4—C19	−169.9 (3)
O7—C8—C9—C4	178.90 (17)	O5—C22—O6—C23	1.6 (5)
C7—C8—C9—C4	−1.7 (3)	C18—C22—O6—C23	−176.8 (3)
C5—C4—C9—C8	2.0 (3)	C24—C23—O6—C22	75.7 (6)
C3—C4—C9—C8	−179.87 (18)	C24'—C23—O6—C22	121.2 (6)
C15—C10—C11—C12	−0.2 (3)	C9—C8—O7—C25	6.9 (3)
S1—C10—C11—C12	179.85 (18)	C7—C8—O7—C25	−172.56 (19)
C10—C11—C12—C13	0.0 (4)	C2—N1—S1—O1	−167.59 (16)
C11—C12—C13—C14	0.2 (4)	C5—N1—S1—O1	30.90 (18)
C12—C13—C14—C15	−0.1 (5)	C2—N1—S1—O2	−37.54 (18)
C11—C10—C15—C14	0.3 (4)	C5—N1—S1—O2	160.94 (15)
S1—C10—C15—C14	−179.8 (2)	C2—N1—S1—C10	77.54 (17)
C13—C14—C15—C10	−0.1 (4)	C5—N1—S1—C10	−83.98 (16)
C2—C3—C17—C18	41.7 (3)	C15—C10—S1—O1	−34.6 (2)
C4—C3—C17—C18	−144.1 (2)	C11—C10—S1—O1	145.35 (17)
C3—C17—C18—C22	−179.7 (2)	C15—C10—S1—O2	−167.21 (18)
C3—C17—C18—C19	6.6 (4)	C11—C10—S1—O2	12.7 (2)
C17—C18—C19—O3	57.7 (3)	C15—C10—S1—N1	78.50 (19)
C22—C18—C19—O3	−116.4 (2)	C11—C10—S1—N1	−101.59 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.32	2.901 (3)	120
C14—H14···O5ⁱ	0.93	2.42	3.349 (3)	173
C25—H25C···Cg1ⁱⁱ	0.96	2.92	3.515 (3)	140

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₅NO₇S
M_r	471.51
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.7597 (2), 10.9029 (2), 12.5186 (3)
α, β, γ (°)	88.402 (1), 79.723 (1), 83.635 (2)
V (Å³)	1169.13 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.22 × 0.18 × 0.15

Data collection
Diffractometer	Bruker Kappa-APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.964, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	27454, 6218, 4628
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.684

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.176, 1.07
No. of reflections	6218
No. of parameters	309
No. of restraints	16
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.45

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
C6—H6···O1	0.93	2.32	2.901 (3)	120
C14—H14···O5ⁱ	0.93	2.42	3.349 (3)	173
C25—H25C···Cg1ⁱⁱ	0.96	2.92	3.515 (3)	140

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

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
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o1139. Web of Science CSD CrossRef IUCr Journals Google Scholar
El-Sayed, K., Barnhart, D. M., Ammon, H. L. & Wassel, G. M. (1986). Acta Cryst. C42, 1383–1385. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Farhanullah, S. A., Maulik, P. R. & Ji Ram, V. (2004). Tetrahedron Lett. 45, 5099–5102. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Okabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386–387. Web of Science CSD CrossRef IUCr Journals Google Scholar
Schollmeyer, D., Fischer, G. & Pindur, U. (1995). Acta Cryst. C51, 2572–2575. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2001). SADABS. University of Go¨ttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 6| June 2009| Pages o1418-o1419

doi:10.1107/S1600536809019369

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

Di­ethyl 2-[(5-meth­­oxy-2-methyl-1-phenyl­sulfonyl-1H-indol-3-yl)methyl­ene]malonate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Diethyl 2-[(5-methoxy-2-methyl-1-phenylsulfonyl-1H-indol-3-yl)methylene]malonate