Methyl (2E)-2-({2-[(2E)-2-benzyl­idene-3-meth­oxy-3-oxoprop­yl]-1,3-dioxoindan-2-yl}meth­yl)-3-phenyl­prop-2-enoate

Lakshmanan, D.; Murugavel, S.; Kannan, D.; Bakthadoss, M.

doi:10.1107/S1600536812017965

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1563-o1564

doi:10.1107/S1600536812017965

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Methyl (2E)-2-({2-[(2E)-2-benzylidene-3-methoxy-3-oxopropyl]-1,3-dioxoindan-2-yl}methyl)-3-phenylprop-2-enoate

D. Lakshmanan,^a S. Murugavel,^b ^* D. Kannan ^c and M. Bakthadoss ^c ‡

^aDepartment of Physics, C. Abdul Hakeem College of Engineering & Technology, Melvisharam, Vellore 632 509, India, ^bDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, and ^cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
^*Correspondence e-mail: smurugavel27@gmail.com

(Received 8 April 2012; accepted 22 April 2012; online 28 April 2012)

In the title compound, C₃₁H₂₆O₆, the five-membered ring of the indane unit adopts a slight envelope conformation with the flap atom displaced by 1.38 (14) Å. The molecular conformation is stabilized by an intramolecular C—H⋯O hydrogen bond, which generates an S(9) ring motif. In the crystal, pairs of C—H⋯O hydrogen bonds link centrosymmetrically related molecules into dimers, generating R₂²(22) ring motifs. The crystal packing is further stabilized by C—H⋯π interactions.

Related literature

Indene ring systems are present in a large number of biologically active compounds, and their metallocene complexes are able to catalyse olefin polymerization, see: Rayabarapu et al. (2003 ); Senanayake et al. (1995 ). For ring puckering analysis, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₃₁H₂₆O₆
M_r = 494.52
Triclinic, $[P \overline 1]$
a = 10.5657 (4) Å
b = 10.9275 (5) Å
c = 11.8961 (5) Å
α = 71.250 (2)°
β = 77.889 (3)°
γ = 76.656 (2)°
V = 1251.70 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.25 × 0.23 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.978, T_max = 0.985
25995 measured reflections
6921 independent reflections
5016 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.128
S = 1.04
6921 reflections
337 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C13–C18 and C24–C29 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1	0.93	2.40	3.288 (2)	161
C27—H27⋯O2ⁱ	0.93	2.46	3.207 (2)	137
C31—H31C⋯Cg1ⁱⁱ	0.96	2.87	3.554 (2)	129
C20—H20B⋯Cg2ⁱⁱⁱ	0.96	2.86	3.500 (2)	125
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+1, -z; (iii) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812017965/bt5874sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812017965/bt5874Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812017965/bt5874Isup3.cml

checkCIF report

Comment top

Indene ring frameworks are present in a large number of biologically active compounds, and their metallocene complexes are able to catalyze olefin polymerization (Senanayake et al., 1995; Rayabarapu et al., 2003). Some derivatives have shown analgesic and myorelaxation activity, and others are used as valuable intermediates for the synthesis of indenyl chrysanthemates that possess insecticidal properties. So in the recent three decades, many chemists have been attracted by the synthesis of indenes. In view of this biological importance, the crystal structure of the title compound has been determined and the results are presented here.

Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The cyclopentane (C1/C2/C3/C8/C9) ring adopts an envelope conformation with the C1 [displacement = 1.38 (14) Å] atom as the flap atom and with puckering parameters (Cremer & Pople, 1975), q₂ = 0.1418 (13) Å and ϕ₂ = 184.2 (6)°. The indene (C1–C9) moeity forms dihedral angles of 50.0 (1)° and 22.7 (1)° respectively, with the C13–C18 and C24–C29 benzene rings. The dihedral angle between two benzene rings is 65.0 (1)°.

The molecular structure is stabilized by C14—H14···O1 intramolecular hydrogen bond, forming S(9) ring motif (Bernstein et al., 1995) (Table 1). In the crystal packing (Fig. 2), the molecules at x, y, z and 1 - x,-y,1 - z are linked by C27—H27··· O2 hydrogen bonds into cyclic centrosymmetric R₂²(22) dimers. The crystal packing is further stabilized by two C—H···π interactions, the first one between a methyl H31C atom and neighbouring benene ring (C13–C18), with a C31—H31C···Cg1ⁱⁱ seperation of 2.87 Å (Fig. 3 and Table 1; Cg1 is the centroid of the C13–C18 benzene ring, Symmetry code as in Fig.3), and the second one between another methyl H20B atom and neighbouring benzene ring (C24–C29), with a C20—H20B···Cg2ⁱⁱⁱ seperation of 2.86 Å (Fig. 3 and Table 1; Cg2 is the centroid of the C24–C29 benzene ring, Symmetry code as in Fig.3).

Related literature top

Indene ring frameworks are present in a large number of biologically activecompounds, and their metallocene complexes are able to catalyse olefin polymerization, see: Rayabarapu et al. (2003); Senanayake et al. (1995). For ring puckering analysis, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

To a stirred solution of 2,3-dihydro-1H-indene-1,3-dione (1 mmol, 0.146 g) and potassium carbonate (2.5 mmol, 0.345 g) was stirred for 15 minutes in acetonitrile as solvent at room temperature. To this solution, methyl (2Z)-2-(bromomethyl) -3-phenylprop-2-enoate (2 mmol, 0.510 g) was added till the addition is complete. After the completion of the reaction as indicated by TLC, acetonitrile solvent was evaporated. Ethylacetate (15 ml) and water (15 ml) were added to the crude mass. The organic layer was dried over anhydrous sodium sulfate. Removal of solvent led to the crude product. The pure title compound was obtained as a colorless solid (0.475 g, 96% yield). Recrystallization was carried out using ethylacetate as solvent.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (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. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 10% probability level. H atoms are presented as a small cycles of arbitrary radius.
	Fig. 2. Part of the crystal structure of the title compound showing C—H···O intermolecular hydrogen bonds (dotted lines) generating R²₂(22) centrosymmetric dimer. [Symmetry code: (i) 1 - x, -y, 1 - z].
	Fig. 3. A view of the C—H···π interactions (dotted lines) in the crystal structure of the title compound. Cg1 and Cg2 denotes centroids of the C13–C18 benzene ring and C24–C29 benzene ring, respectively. [Symmetry codes: (ii) -x, 1 - y, -z; (iii) -x, -y, 1 - z].

Methyl (2E)-2-({2-[(2E)-2-benzylidene-3-methoxy-3-oxopropyl]-1,3-dioxoindan-2-yl}methyl)-3-phenylprop-2-enoate top

Crystal data top

C₃₁H₂₆O₆	Z = 2
M_r = 494.52	F(000) = 520
Triclinic, P1	D_x = 1.312 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.5657 (4) Å	Cell parameters from 7169 reflections
b = 10.9275 (5) Å	θ = 2.0–29.8°
c = 11.8961 (5) Å	µ = 0.09 mm⁻¹
α = 71.250 (2)°	T = 293 K
β = 77.889 (3)°	Block, colourless
γ = 76.656 (2)°	0.25 × 0.23 × 0.17 mm
V = 1251.70 (9) Å³

Data collection top

Bruker APEXII CCD diffractometer	6921 independent reflections
Radiation source: fine-focus sealed tube	5016 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 10.0 pixels mm^-1	θ_max = 29.8°, θ_min = 2.0°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −15→15
T_min = 0.978, T_max = 0.985	l = −12→16
25995 measured reflections

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.0592P)² + 0.201P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
6921 reflections	Δρ_max = 0.28 e Å⁻³
337 parameters	Δρ_min = −0.18 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: 0.0071 (18)

Crystal data top

C₃₁H₂₆O₆	γ = 76.656 (2)°
M_r = 494.52	V = 1251.70 (9) Å³
Triclinic, P1	Z = 2
a = 10.5657 (4) Å	Mo Kα radiation
b = 10.9275 (5) Å	µ = 0.09 mm⁻¹
c = 11.8961 (5) Å	T = 293 K
α = 71.250 (2)°	0.25 × 0.23 × 0.17 mm
β = 77.889 (3)°

Data collection top

Bruker APEXII CCD diffractometer	6921 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5016 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.985	R_int = 0.028
25995 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.04	Δρ_max = 0.28 e Å⁻³
6921 reflections	Δρ_min = −0.18 e Å⁻³
337 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
C1	0.25024 (11)	0.03216 (11)	0.19693 (10)	0.0334 (2)
C2	0.29043 (12)	−0.11776 (12)	0.22493 (11)	0.0379 (3)
C3	0.27268 (11)	−0.15476 (12)	0.12061 (11)	0.0357 (3)
C4	0.31247 (13)	−0.27427 (13)	0.09515 (13)	0.0441 (3)
H4	0.3578	−0.3463	0.1468	0.053*
C5	0.28266 (14)	−0.28279 (15)	−0.00914 (14)	0.0508 (4)
H5	0.3097	−0.3616	−0.0288	0.061*
C6	0.21335 (15)	−0.17655 (16)	−0.08524 (14)	0.0525 (4)
H6	0.1929	−0.1857	−0.1541	0.063*
C7	0.17414 (13)	−0.05732 (14)	−0.06069 (12)	0.0455 (3)
H7	0.1277	0.0142	−0.1120	0.055*
C8	0.20613 (11)	−0.04741 (12)	0.04293 (11)	0.0352 (3)
C9	0.17798 (11)	0.06785 (11)	0.08894 (10)	0.0335 (2)
C10	0.17153 (12)	0.08121 (12)	0.30306 (11)	0.0364 (3)
H10A	0.2062	0.0235	0.3749	0.044*
H10B	0.1909	0.1673	0.2916	0.044*
C11	0.02411 (12)	0.09234 (11)	0.32861 (10)	0.0344 (2)
C12	−0.05926 (13)	0.20136 (12)	0.33956 (12)	0.0395 (3)
H12	−0.1460	0.1918	0.3706	0.047*
C13	−0.03082 (12)	0.33552 (12)	0.30845 (12)	0.0404 (3)
C14	0.02253 (14)	0.39710 (14)	0.19283 (14)	0.0496 (3)
H14	0.0492	0.3504	0.1364	0.060*
C15	0.03664 (16)	0.52755 (15)	0.16017 (17)	0.0594 (4)
H15	0.0699	0.5686	0.0815	0.071*
C16	0.00162 (16)	0.59609 (15)	0.24355 (18)	0.0610 (4)
H16	0.0123	0.6832	0.2221	0.073*
C17	−0.04925 (17)	0.53541 (15)	0.35889 (17)	0.0610 (4)
H17	−0.0714	0.5814	0.4158	0.073*
C18	−0.06809 (16)	0.40642 (14)	0.39177 (14)	0.0517 (3)
H18	−0.1056	0.3675	0.4695	0.062*
C19	−0.02906 (13)	−0.02882 (12)	0.34965 (11)	0.0389 (3)
C20	−0.21535 (18)	−0.13120 (16)	0.41099 (18)	0.0694 (5)
H20A	−0.2102	−0.1496	0.3363	0.104*
H20B	−0.3058	−0.1147	0.4460	0.104*
H20C	−0.1688	−0.2052	0.4648	0.104*
C21	0.38551 (12)	0.08067 (12)	0.16164 (12)	0.0387 (3)
H21A	0.4251	0.0591	0.2337	0.046*
H21B	0.4434	0.0330	0.1089	0.046*
C22	0.37728 (11)	0.22488 (13)	0.10063 (11)	0.0379 (3)
C23	0.38335 (13)	0.31646 (13)	0.15049 (12)	0.0411 (3)
H23	0.3673	0.4022	0.1013	0.049*
C24	0.41114 (12)	0.30482 (12)	0.27018 (12)	0.0392 (3)
C25	0.51220 (13)	0.21207 (14)	0.32403 (13)	0.0459 (3)
H25	0.5591	0.1478	0.2881	0.055*
C26	0.54314 (14)	0.21504 (16)	0.43022 (14)	0.0529 (4)
H26	0.6109	0.1528	0.4650	0.063*
C27	0.47525 (16)	0.30853 (17)	0.48491 (14)	0.0569 (4)
H27	0.4971	0.3102	0.5561	0.068*
C28	0.37445 (16)	0.39995 (16)	0.43375 (14)	0.0549 (4)
H28	0.3275	0.4632	0.4709	0.066*
C29	0.34272 (14)	0.39827 (13)	0.32762 (13)	0.0463 (3)
H29	0.2744	0.4607	0.2939	0.056*
C30	0.36793 (13)	0.26335 (14)	−0.02990 (12)	0.0437 (3)
C31	0.3415 (2)	0.4347 (2)	−0.20839 (15)	0.0730 (5)
H31A	0.4247	0.4020	−0.2489	0.110*
H31B	0.3243	0.5289	−0.2364	0.110*
H31C	0.2732	0.4010	−0.2247	0.110*
O1	0.10725 (9)	0.17082 (9)	0.05059 (8)	0.0454 (2)
O2	0.33508 (11)	−0.18975 (10)	0.31315 (9)	0.0565 (3)
O3	−0.15730 (10)	−0.01759 (9)	0.38974 (10)	0.0549 (3)
O4	0.03542 (11)	−0.12708 (10)	0.32961 (12)	0.0659 (3)
O5	0.34473 (12)	0.39300 (10)	−0.08061 (9)	0.0581 (3)
O6	0.38424 (11)	0.18503 (11)	−0.08508 (9)	0.0588 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0328 (5)	0.0355 (6)	0.0339 (6)	−0.0033 (4)	−0.0080 (5)	−0.0124 (5)
C2	0.0363 (6)	0.0370 (6)	0.0400 (7)	−0.0031 (5)	−0.0089 (5)	−0.0107 (5)
C3	0.0314 (5)	0.0373 (6)	0.0389 (6)	−0.0072 (5)	−0.0020 (5)	−0.0129 (5)
C4	0.0413 (7)	0.0373 (6)	0.0543 (8)	−0.0094 (5)	−0.0011 (6)	−0.0160 (6)
C5	0.0496 (8)	0.0499 (8)	0.0620 (9)	−0.0160 (6)	0.0051 (7)	−0.0316 (7)
C6	0.0507 (8)	0.0688 (10)	0.0513 (8)	−0.0167 (7)	−0.0036 (6)	−0.0337 (8)
C7	0.0428 (7)	0.0575 (8)	0.0408 (7)	−0.0080 (6)	−0.0090 (6)	−0.0192 (6)
C8	0.0314 (6)	0.0405 (6)	0.0357 (6)	−0.0072 (5)	−0.0033 (5)	−0.0141 (5)
C9	0.0301 (5)	0.0375 (6)	0.0323 (6)	−0.0052 (4)	−0.0038 (4)	−0.0101 (5)
C10	0.0394 (6)	0.0395 (6)	0.0335 (6)	−0.0062 (5)	−0.0070 (5)	−0.0142 (5)
C11	0.0402 (6)	0.0346 (6)	0.0295 (6)	−0.0086 (5)	−0.0023 (5)	−0.0109 (5)
C12	0.0383 (6)	0.0384 (6)	0.0428 (7)	−0.0099 (5)	0.0010 (5)	−0.0153 (5)
C13	0.0372 (6)	0.0356 (6)	0.0507 (7)	−0.0030 (5)	−0.0072 (5)	−0.0174 (6)
C14	0.0503 (8)	0.0433 (7)	0.0570 (9)	−0.0119 (6)	0.0022 (6)	−0.0205 (6)
C15	0.0567 (9)	0.0449 (8)	0.0729 (11)	−0.0169 (7)	0.0007 (8)	−0.0130 (7)
C16	0.0551 (9)	0.0371 (7)	0.0962 (13)	−0.0076 (6)	−0.0189 (9)	−0.0217 (8)
C17	0.0724 (10)	0.0440 (8)	0.0787 (12)	0.0041 (7)	−0.0265 (9)	−0.0344 (8)
C18	0.0603 (9)	0.0432 (7)	0.0536 (8)	0.0021 (6)	−0.0142 (7)	−0.0207 (6)
C19	0.0453 (7)	0.0360 (6)	0.0339 (6)	−0.0095 (5)	0.0016 (5)	−0.0111 (5)
C20	0.0665 (10)	0.0526 (9)	0.0910 (13)	−0.0333 (8)	0.0190 (9)	−0.0265 (9)
C21	0.0317 (6)	0.0418 (6)	0.0442 (7)	−0.0032 (5)	−0.0073 (5)	−0.0155 (5)
C22	0.0298 (5)	0.0454 (7)	0.0386 (6)	−0.0076 (5)	−0.0044 (5)	−0.0118 (5)
C23	0.0407 (6)	0.0418 (7)	0.0405 (7)	−0.0106 (5)	−0.0073 (5)	−0.0085 (5)
C24	0.0365 (6)	0.0425 (7)	0.0405 (7)	−0.0140 (5)	−0.0049 (5)	−0.0100 (5)
C25	0.0363 (6)	0.0542 (8)	0.0496 (8)	−0.0072 (6)	−0.0054 (6)	−0.0192 (6)
C26	0.0405 (7)	0.0676 (9)	0.0510 (8)	−0.0086 (6)	−0.0135 (6)	−0.0139 (7)
C27	0.0559 (9)	0.0772 (11)	0.0461 (8)	−0.0196 (8)	−0.0102 (7)	−0.0223 (8)
C28	0.0583 (9)	0.0600 (9)	0.0536 (9)	−0.0114 (7)	−0.0029 (7)	−0.0286 (7)
C29	0.0455 (7)	0.0440 (7)	0.0509 (8)	−0.0093 (6)	−0.0072 (6)	−0.0144 (6)
C30	0.0355 (6)	0.0536 (8)	0.0428 (7)	−0.0125 (5)	−0.0025 (5)	−0.0135 (6)
C31	0.0816 (12)	0.0871 (13)	0.0457 (9)	−0.0209 (10)	−0.0202 (8)	−0.0016 (9)
O1	0.0458 (5)	0.0430 (5)	0.0455 (5)	0.0049 (4)	−0.0157 (4)	−0.0133 (4)
O2	0.0703 (7)	0.0465 (6)	0.0492 (6)	0.0059 (5)	−0.0277 (5)	−0.0085 (5)
O3	0.0466 (5)	0.0408 (5)	0.0757 (7)	−0.0176 (4)	0.0115 (5)	−0.0207 (5)
O4	0.0585 (6)	0.0452 (6)	0.0961 (9)	−0.0152 (5)	0.0167 (6)	−0.0367 (6)
O5	0.0748 (7)	0.0553 (6)	0.0427 (6)	−0.0113 (5)	−0.0180 (5)	−0.0061 (5)
O6	0.0670 (7)	0.0698 (7)	0.0467 (6)	−0.0169 (5)	−0.0023 (5)	−0.0268 (5)

Geometric parameters (Å, º) top

C1—C9	1.5289 (16)	C17—C18	1.386 (2)
C1—C10	1.5368 (17)	C17—H17	0.9300
C1—C2	1.5370 (17)	C18—H18	0.9300
C1—C21	1.5668 (16)	C19—O4	1.1970 (15)
C2—O2	1.2035 (15)	C19—O3	1.3297 (16)
C2—C3	1.4812 (17)	C20—O3	1.4374 (17)
C3—C8	1.3855 (17)	C20—H20A	0.9600
C3—C4	1.3862 (17)	C20—H20B	0.9600
C4—C5	1.378 (2)	C20—H20C	0.9600
C4—H4	0.9300	C21—C22	1.4985 (18)
C5—C6	1.383 (2)	C21—H21A	0.9700
C5—H5	0.9300	C21—H21B	0.9700
C6—C7	1.378 (2)	C22—C23	1.3359 (18)
C6—H6	0.9300	C22—C30	1.4911 (19)
C7—C8	1.3868 (17)	C23—C24	1.4735 (18)
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.4752 (17)	C24—C29	1.3902 (19)
C9—O1	1.2073 (14)	C24—C25	1.3957 (19)
C10—C11	1.5070 (17)	C25—C26	1.381 (2)
C10—H10A	0.9700	C25—H25	0.9300
C10—H10B	0.9700	C26—C27	1.369 (2)
C11—C12	1.3339 (17)	C26—H26	0.9300
C11—C19	1.4841 (17)	C27—C28	1.376 (2)
C12—C13	1.4779 (17)	C27—H27	0.9300
C12—H12	0.9300	C28—C29	1.379 (2)
C13—C14	1.385 (2)	C28—H28	0.9300
C13—C18	1.3882 (19)	C29—H29	0.9300
C14—C15	1.387 (2)	C30—O6	1.1994 (17)
C14—H14	0.9300	C30—O5	1.3354 (17)
C15—C16	1.370 (2)	C31—O5	1.4453 (19)
C15—H15	0.9300	C31—H31A	0.9600
C16—C17	1.372 (3)	C31—H31B	0.9600
C16—H16	0.9300	C31—H31C	0.9600

C9—C1—C10	114.88 (10)	C16—C17—H17	119.5
C9—C1—C2	102.63 (9)	C18—C17—H17	119.5
C10—C1—C2	114.96 (10)	C17—C18—C13	119.89 (15)
C9—C1—C21	112.06 (10)	C17—C18—H18	120.1
C10—C1—C21	108.52 (9)	C13—C18—H18	120.1
C2—C1—C21	103.19 (9)	O4—C19—O3	122.35 (12)
O2—C2—C3	126.87 (12)	O4—C19—C11	123.84 (12)
O2—C2—C1	125.44 (12)	O3—C19—C11	113.78 (10)
C3—C2—C1	107.57 (10)	O3—C20—H20A	109.5
C8—C3—C4	120.86 (12)	O3—C20—H20B	109.5
C8—C3—C2	109.67 (10)	H20A—C20—H20B	109.5
C4—C3—C2	129.47 (12)	O3—C20—H20C	109.5
C5—C4—C3	117.82 (13)	H20A—C20—H20C	109.5
C5—C4—H4	121.1	H20B—C20—H20C	109.5
C3—C4—H4	121.1	C22—C21—C1	114.63 (10)
C4—C5—C6	121.34 (13)	C22—C21—H21A	108.6
C4—C5—H5	119.3	C1—C21—H21A	108.6
C6—C5—H5	119.3	C22—C21—H21B	108.6
C7—C6—C5	121.08 (13)	C1—C21—H21B	108.6
C7—C6—H6	119.5	H21A—C21—H21B	107.6
C5—C6—H6	119.5	C23—C22—C30	119.34 (12)
C6—C7—C8	117.83 (13)	C23—C22—C21	126.49 (12)
C6—C7—H7	121.1	C30—C22—C21	114.10 (11)
C8—C7—H7	121.1	C22—C23—C24	131.01 (12)
C3—C8—C7	121.04 (12)	C22—C23—H23	114.5
C3—C8—C9	110.18 (10)	C24—C23—H23	114.5
C7—C8—C9	128.78 (12)	C29—C24—C25	117.80 (12)
O1—C9—C8	126.17 (11)	C29—C24—C23	118.80 (12)
O1—C9—C1	125.91 (11)	C25—C24—C23	123.09 (12)
C8—C9—C1	107.88 (9)	C26—C25—C24	120.52 (13)
C11—C10—C1	120.19 (10)	C26—C25—H25	119.7
C11—C10—H10A	107.3	C24—C25—H25	119.7
C1—C10—H10A	107.3	C27—C26—C25	120.79 (14)
C11—C10—H10B	107.3	C27—C26—H26	119.6
C1—C10—H10B	107.3	C25—C26—H26	119.6
H10A—C10—H10B	106.9	C26—C27—C28	119.49 (14)
C12—C11—C19	118.89 (11)	C26—C27—H27	120.3
C12—C11—C10	124.08 (11)	C28—C27—H27	120.3
C19—C11—C10	116.93 (10)	C27—C28—C29	120.30 (14)
C11—C12—C13	128.02 (12)	C27—C28—H28	119.8
C11—C12—H12	116.0	C29—C28—H28	119.8
C13—C12—H12	116.0	C28—C29—C24	121.09 (13)
C14—C13—C18	118.65 (12)	C28—C29—H29	119.5
C14—C13—C12	120.66 (12)	C24—C29—H29	119.5
C18—C13—C12	120.43 (13)	O6—C30—O5	123.11 (13)
C13—C14—C15	120.79 (14)	O6—C30—C22	123.02 (13)
C13—C14—H14	119.6	O5—C30—C22	113.82 (12)
C15—C14—H14	119.6	O5—C31—H31A	109.5
C16—C15—C14	120.12 (16)	O5—C31—H31B	109.5
C16—C15—H15	119.9	H31A—C31—H31B	109.5
C14—C15—H15	119.9	O5—C31—H31C	109.5
C15—C16—C17	119.57 (14)	H31A—C31—H31C	109.5
C15—C16—H16	120.2	H31B—C31—H31C	109.5
C17—C16—H16	120.2	C19—O3—C20	116.63 (11)
C16—C17—C18	120.93 (14)	C30—O5—C31	115.67 (13)

C9—C1—C2—O2	−169.81 (13)	C11—C12—C13—C18	−127.96 (15)
C10—C1—C2—O2	−44.38 (17)	C18—C13—C14—C15	−1.0 (2)
C21—C1—C2—O2	73.58 (15)	C12—C13—C14—C15	173.24 (14)
C9—C1—C2—C3	13.99 (12)	C13—C14—C15—C16	2.1 (2)
C10—C1—C2—C3	139.42 (10)	C14—C15—C16—C17	−1.0 (3)
C21—C1—C2—C3	−102.62 (10)	C15—C16—C17—C18	−1.2 (2)
O2—C2—C3—C8	173.92 (13)	C16—C17—C18—C13	2.3 (2)
C1—C2—C3—C8	−9.95 (13)	C14—C13—C18—C17	−1.2 (2)
O2—C2—C3—C4	−6.3 (2)	C12—C13—C18—C17	−175.45 (13)
C1—C2—C3—C4	169.83 (12)	C12—C11—C19—O4	171.63 (14)
C8—C3—C4—C5	−0.54 (19)	C10—C11—C19—O4	−11.90 (19)
C2—C3—C4—C5	179.70 (12)	C12—C11—C19—O3	−6.35 (17)
C3—C4—C5—C6	−1.1 (2)	C10—C11—C19—O3	170.13 (11)
C4—C5—C6—C7	1.5 (2)	C9—C1—C21—C22	55.81 (13)
C5—C6—C7—C8	−0.2 (2)	C10—C1—C21—C22	−72.09 (13)
C4—C3—C8—C7	1.85 (19)	C2—C1—C21—C22	165.52 (10)
C2—C3—C8—C7	−178.35 (11)	C1—C21—C22—C23	102.49 (14)
C4—C3—C8—C9	−178.62 (11)	C1—C21—C22—C30	−80.62 (13)
C2—C3—C8—C9	1.18 (14)	C30—C22—C23—C24	−170.34 (12)
C6—C7—C8—C3	−1.47 (19)	C21—C22—C23—C24	6.4 (2)
C6—C7—C8—C9	179.09 (12)	C22—C23—C24—C29	−142.60 (15)
C3—C8—C9—O1	−169.82 (12)	C22—C23—C24—C25	44.0 (2)
C7—C8—C9—O1	9.7 (2)	C29—C24—C25—C26	−0.69 (19)
C3—C8—C9—C1	8.11 (13)	C23—C24—C25—C26	172.75 (13)
C7—C8—C9—C1	−172.40 (12)	C24—C25—C26—C27	0.2 (2)
C10—C1—C9—O1	39.12 (17)	C25—C26—C27—C28	0.5 (2)
C2—C1—C9—O1	164.60 (12)	C26—C27—C28—C29	−0.6 (2)
C21—C1—C9—O1	−85.33 (14)	C27—C28—C29—C24	0.1 (2)
C10—C1—C9—C8	−138.82 (10)	C25—C24—C29—C28	0.6 (2)
C2—C1—C9—C8	−13.33 (12)	C23—C24—C29—C28	−173.17 (13)
C21—C1—C9—C8	96.74 (11)	C23—C22—C30—O6	167.08 (13)
C9—C1—C10—C11	32.08 (15)	C21—C22—C30—O6	−10.05 (18)
C2—C1—C10—C11	−86.71 (13)	C23—C22—C30—O5	−10.50 (17)
C21—C1—C10—C11	158.36 (10)	C21—C22—C30—O5	172.37 (11)
C1—C10—C11—C12	−126.37 (13)	O4—C19—O3—C20	1.5 (2)
C1—C10—C11—C19	57.36 (15)	C11—C19—O3—C20	179.47 (13)
C19—C11—C12—C13	−171.64 (12)	O6—C30—O5—C31	−0.5 (2)
C10—C11—C12—C13	12.2 (2)	C22—C30—O5—C31	177.03 (13)
C11—C12—C13—C14	57.91 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C13–C18 and C24–C29 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1	0.93	2.40	3.288 (2)	161
C27—H27···O2ⁱ	0.93	2.46	3.207 (2)	137
C31—H31C···Cg1ⁱⁱ	0.96	2.87	3.554 (2)	129
C20—H20B···Cg2ⁱⁱⁱ	0.96	2.86	3.500 (2)	125

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

Experimental details

Crystal data
Chemical formula	C₃₁H₂₆O₆
M_r	494.52
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.5657 (4), 10.9275 (5), 11.8961 (5)
α, β, γ (°)	71.250 (2), 77.889 (3), 76.656 (2)
V (Å³)	1251.70 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.23 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.978, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	25995, 6921, 5016
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.699

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.128, 1.04
No. of reflections	6921
No. of parameters	337
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.18

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C13–C18 and C24–C29 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1	0.93	2.40	3.288 (2)	161.0
C27—H27···O2ⁱ	0.93	2.46	3.207 (2)	137.3
C31—H31C···Cg1ⁱⁱ	0.96	2.87	3.554 (2)	129.0
C20—H20B···Cg2ⁱⁱⁱ	0.96	2.86	3.500 (2)	125.0

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

Footnotes

‡Additional correspondence author, e-mail: bhakthadoss@yahoo.com.

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Rayabarapu, D. K., Yang, C. H. & Cheng, C. H. (2003). J. Org. Chem. 68, 6726–6731. Web of Science CrossRef PubMed CAS Google Scholar
Senanayake, C. H., Roberts, F. E., DiMichele, L. M., Ryan, K. M., Liu, J., Fredenburgh, L. E., Foster, B. S., Douglas, A. W., Larsen, R. D., Verhoeven, T. R. & Reider, P. J. (1995). Tetrahedron Lett. 36, 3993–3996. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). 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. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 5| May 2012| Pages o1563-o1564

doi:10.1107/S1600536812017965

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

Methyl (2E)-2-({2-[(2E)-2-benzyl­­idene-3-meth­­oxy-3-oxoprop­yl]-1,3-dioxoindan-2-yl}meth­yl)-3-phenyl­prop-2-enoate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Methyl (2E)-2-({2-[(2E)-2-benzylidene-3-methoxy-3-oxopropyl]-1,3-dioxoindan-2-yl}methyl)-3-phenylprop-2-enoate