Ethyl 2-cyano-5-oxo-5-(thio­phen-2-yl)-3-(3,4,5-trimeth­oxy­phen­yl)penta­noate

Prabhuswamy, M.; Madan Kumar, S.; Raghavendra, K.R.; Abdoh, M.M.M.; Shashikanth, S.; Lokanath, N.K.

doi:10.1107/S1600536812044522

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3275

doi:10.1107/S1600536812044522

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Ethyl 2-cyano-5-oxo-5-(thiophen-2-yl)-3-(3,4,5-trimethoxyphenyl)pentanoate

M. Prabhuswamy,^a S. Madan Kumar,^a K. R. Raghavendra,^b M. M. M. Abdoh,^c S. Shashikanth ^b and N. K. Lokanath ^a ^*

^aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Physics, Faculty of Science, An Najah National University, Nabtus West Bank, Palestinian Territories
^*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

(Received 18 October 2012; accepted 27 October 2012; online 3 November 2012)

In the title compound, C₂₁H₂₃NO₆S, the dihedral angle between the thiopene and benzene rings is 88.66 (6)°. In the crystal, molecules are connected by C—H⋯N and C—H⋯O hydrogen bonds, forming a tape along [10-1]. In addition, C—H⋯π and π–π stacking [centroid–centroid distance = 3.879 (2) Å between the thiophene rings] interactions are observed.

Related literature

For applications of thiophenes, see: Günther & Steinmetz (1963 ). For a similar structure, see: Harrison et al. (2010 ).

Experimental

Crystal data

C₂₁H₂₃NO₆S
M_r = 417.47
Triclinic, $[P \overline 1]$
a = 8.4308 (5) Å
b = 10.5025 (6) Å
c = 12.3059 (6) Å
α = 98.530 (2)°
β = 107.950 (2)°
γ = 97.966 (3)°
V = 1005.26 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.22 × 0.20 × 0.19 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
16712 measured reflections
3965 independent reflections
3498 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.080
S = 1.04
3965 reflections
266 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1ⁱ	0.93	2.49	3.368 (2)	157
C18—H18B⋯O2ⁱⁱ	0.96	2.56	3.385 (2)	143
C17—H17A⋯Cg2ⁱⁱⁱ	0.96	2.85	3.6327 (16)	139
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: Mercury.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812044522/is5211sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812044522/is5211Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812044522/is5211Isup3.cml

checkCIF report

Comment top

Thiophenes have importance to give cycloaddition products with carbenes (Günther et al.,1963). In the title molecule, C₂₁H₂₃NO₆S (Fig. 1.), the thiopene ring is basically planar and its geometry is similar to (2E)-3-(1,3-benzodioxol-5-yl)-1-(3-bromo-2-thienyl)prop-2-en-1-one (Harrison et al., 2010). The dihedral angle between the thiopene ring and the trimethoxyphenyl unit is 88.66 (6)°, which signifies the thiopene ring is almost perpendicular to the trimethoxyphenyl unit. The molecules are connected by C—H···N and C—H···O interactions (Table 1) into a tape structure (Fig. 2). In addition, the crystal is stabilized with π–π stacking interactions between thiophene rings, related by unit translation along the a axis with the distance of 3.879 (2) Å [-x+1, -y+1, -z+1]. Also, short contacts C—H···π (Table 1) and C—O···π with a distance of 3.733 (1) Å [87.10 (9)°] [x+1, y, z] are present.

Related literature top

For applications of thiophenes, see: Günther & Steinmetz (1963). For a similar structure, see: Harrison et al. (2010).

Experimental top

Freshly distilled ethyl cyanoacetate (8.5 g, 0.72 mol) was added in to a stirred suspension of powdered sodium (2.51 g, 0.109 mol) in dry benzene (40 ml) at room temperature. To this mixture Chalcone-1{3-(benzo[1,3] dioxol-5-yl)-1(thiophene-2-yl)prop-2-ene-1-one} was added and stirred for 36 hrs, at room temperature. Salts were filtered off, the filterate was with 5% NaOH (100 ml), brine solution (100 ml), and dried over anhydrous sodium sulfate. Concentration of the solvent furnished crude product, which was purified by column chromatography using benzene-ethyl acetate (8:2) as eluent gave ethyl 2-cyano-5-oxo-5-(thiophen-2-yl)-3-(3,4,5-trimethoxyphenyl)pentanoate as pale yellow oily product in 78% yield (14.5 g). Recrystallization with benzene led to the formation of the crystals.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: Mercury (Macrae et al., 2006).

Figures top

	Fig. 1. An ORTEP diagram of the title compound with 50% probability ellipsoids.
	Fig. 2. A packing diagram of the title compound, viewed along the a-axis. C—H···N and C—H···O hydrogen bonds are indicated by dashed lines.

Ethyl 2-cyano-5-oxo-5-(thiophen-2-yl)-3-(3,4,5-trimethoxyphenyl)pentanoate top

Crystal data top

C₂₁H₂₃NO₆S	Z = 2
M_r = 417.47	F(000) = 440
Triclinic, P1	D_x = 1.379 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4308 (5) Å	Cell parameters from 3965 reflections
b = 10.5025 (6) Å	θ = 1.8–26.0°
c = 12.3059 (6) Å	µ = 0.20 mm⁻¹
α = 98.530 (2)°	T = 296 K
β = 107.950 (2)°	Block, white
γ = 97.966 (3)°	0.22 × 0.20 × 0.19 mm
V = 1005.26 (10) Å³

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3498 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 26.0°, θ_min = 1.8°
Detector resolution: 16.0839 pixels mm^-1	h = −10→10
ω scans	k = −12→12
16712 measured reflections	l = −15→15
3965 independent reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0336P)² + 0.4919P] where P = (F_o² + 2F_c²)/3
3965 reflections	(Δ/σ)_max < 0.001
266 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₁H₂₃NO₆S	γ = 97.966 (3)°
M_r = 417.47	V = 1005.26 (10) Å³
Triclinic, P1	Z = 2
a = 8.4308 (5) Å	Mo Kα radiation
b = 10.5025 (6) Å	µ = 0.20 mm⁻¹
c = 12.3059 (6) Å	T = 296 K
α = 98.530 (2)°	0.22 × 0.20 × 0.19 mm
β = 107.950 (2)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3498 reflections with I > 2σ(I)
16712 measured reflections	R_int = 0.027
3965 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.04	Δρ_max = 0.30 e Å⁻³
3965 reflections	Δρ_min = −0.29 e Å⁻³
266 parameters

Special details top

Experimental. IR: 2249 cm^-1 (CN), 1758 cm^-1 (esterCO). ¹H NMR: 400 MHz (CDCl₃) δ: 7.8 (1H, s), 7.3 (1H, s), 7.15 (1H, s), 6.6 (2H, s), 4.3 (1H, m), 4.2 (2H, q), 3.91 (1H, d), 3.88(6H, s), 3.8 (3H, s), 3.58 (2H, d), 1.23 (3H, t). MS: (M⁺+1): 417.114.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.28565 (5)	1.06346 (3)	0.11584 (3)	0.0210 (1)
O1	0.51411 (14)	0.95781 (10)	0.30335 (8)	0.0242 (3)
O2	0.30973 (12)	0.61342 (9)	0.55116 (8)	0.0190 (3)
O3	0.05123 (12)	0.47024 (9)	0.37057 (8)	0.0185 (3)
O4	0.07586 (12)	0.41627 (10)	0.15717 (8)	0.0196 (3)
O5	0.97151 (12)	0.73365 (10)	0.20324 (8)	0.0209 (3)
O6	1.01797 (12)	0.78955 (9)	0.39592 (8)	0.0170 (3)
N1	0.65206 (15)	0.45085 (12)	0.09731 (11)	0.0234 (4)
C1	0.18369 (17)	1.03613 (14)	−0.03091 (12)	0.0200 (4)
C2	0.21615 (18)	0.92745 (14)	−0.08935 (12)	0.0207 (4)
C3	0.32723 (18)	0.86473 (14)	−0.01290 (12)	0.0193 (4)
C4	0.37613 (17)	0.92704 (13)	0.10141 (12)	0.0160 (4)
C5	0.49077 (17)	0.89505 (13)	0.20599 (11)	0.0161 (4)
C6	0.58474 (17)	0.78544 (13)	0.18750 (11)	0.0156 (4)
C7	0.63629 (16)	0.72138 (12)	0.29378 (11)	0.0139 (3)
C8	0.48318 (16)	0.64602 (12)	0.31321 (11)	0.0140 (3)
C9	0.47425 (17)	0.66368 (13)	0.42533 (11)	0.0146 (3)
C10	0.33230 (17)	0.60120 (13)	0.44517 (11)	0.0152 (4)
C11	0.19780 (17)	0.52151 (13)	0.35220 (11)	0.0150 (4)
C12	0.21070 (16)	0.49990 (13)	0.24072 (11)	0.0153 (3)
C13	0.35232 (17)	0.56266 (13)	0.22062 (11)	0.0151 (4)
C14	0.77024 (16)	0.63512 (13)	0.28577 (11)	0.0147 (4)
C15	0.93232 (17)	0.72248 (13)	0.28766 (11)	0.0149 (3)
C17	0.44421 (18)	0.69491 (14)	0.64868 (11)	0.0201 (4)
C18	0.03823 (19)	0.33577 (14)	0.37964 (13)	0.0224 (4)
C19	0.09595 (18)	0.37209 (14)	0.04739 (12)	0.0216 (4)
C20	0.70638 (17)	0.53120 (13)	0.17950 (12)	0.0168 (4)
C21	1.17352 (17)	0.88197 (14)	0.41028 (12)	0.0202 (4)
C22	1.1345 (2)	1.00956 (14)	0.37958 (13)	0.0243 (4)
H1	0.11360	1.08950	−0.06710	0.0240*
H2	0.17080	0.89800	−0.16980	0.0250*
H3	0.36310	0.78930	−0.03780	0.0230*
H6A	0.68590	0.82030	0.17130	0.0190*
H6B	0.51270	0.71930	0.12010	0.0190*
H7	0.69170	0.79260	0.36220	0.0170*
H9	0.56340	0.71740	0.48710	0.0180*
H13	0.35970	0.54910	0.14610	0.0180*
H14	0.79750	0.59380	0.35390	0.0180*
H17A	0.54680	0.66130	0.65800	0.0300*
H17B	0.41450	0.69530	0.71800	0.0300*
H17C	0.46160	0.78280	0.63550	0.0300*
H18A	0.03270	0.28360	0.30710	0.0340*
H18B	−0.06280	0.30720	0.39710	0.0340*
H18C	0.13600	0.32590	0.44090	0.0340*
H19A	0.11030	0.44550	0.01080	0.0320*
H19B	−0.00320	0.30890	−0.00200	0.0320*
H19C	0.19420	0.33230	0.05960	0.0320*
H21A	1.23170	0.84380	0.36060	0.0240*
H21B	1.24880	0.89780	0.49050	0.0240*
H22A	1.06580	0.99480	0.29880	0.0360*
H22B	1.23870	1.06950	0.39310	0.0360*
H22C	1.07400	1.04620	0.42710	0.0360*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0241 (2)	0.0211 (2)	0.0196 (2)	0.0112 (2)	0.0066 (1)	0.0051 (1)
O1	0.0334 (6)	0.0209 (5)	0.0182 (5)	0.0120 (4)	0.0065 (4)	0.0025 (4)
O2	0.0206 (5)	0.0222 (5)	0.0150 (5)	0.0019 (4)	0.0084 (4)	0.0029 (4)
O3	0.0158 (5)	0.0190 (5)	0.0255 (5)	0.0046 (4)	0.0120 (4)	0.0068 (4)
O4	0.0160 (5)	0.0241 (5)	0.0162 (5)	−0.0015 (4)	0.0058 (4)	0.0008 (4)
O5	0.0206 (5)	0.0233 (5)	0.0196 (5)	0.0014 (4)	0.0101 (4)	0.0021 (4)
O6	0.0154 (5)	0.0173 (5)	0.0168 (5)	−0.0002 (4)	0.0046 (4)	0.0036 (4)
N1	0.0211 (6)	0.0187 (6)	0.0283 (7)	0.0050 (5)	0.0073 (5)	−0.0007 (5)
C1	0.0162 (7)	0.0214 (7)	0.0230 (7)	0.0041 (6)	0.0047 (6)	0.0096 (6)
C2	0.0208 (7)	0.0197 (7)	0.0185 (7)	0.0020 (6)	0.0031 (6)	0.0043 (5)
C3	0.0203 (7)	0.0151 (7)	0.0215 (7)	0.0027 (5)	0.0065 (6)	0.0029 (5)
C4	0.0148 (6)	0.0136 (7)	0.0211 (7)	0.0038 (5)	0.0071 (5)	0.0049 (5)
C5	0.0164 (7)	0.0140 (6)	0.0189 (7)	0.0017 (5)	0.0070 (5)	0.0049 (5)
C6	0.0158 (7)	0.0156 (7)	0.0184 (6)	0.0039 (5)	0.0083 (5)	0.0061 (5)
C7	0.0146 (6)	0.0122 (6)	0.0155 (6)	0.0029 (5)	0.0056 (5)	0.0030 (5)
C8	0.0143 (6)	0.0123 (6)	0.0184 (6)	0.0061 (5)	0.0069 (5)	0.0057 (5)
C9	0.0150 (6)	0.0125 (6)	0.0159 (6)	0.0039 (5)	0.0038 (5)	0.0035 (5)
C10	0.0187 (7)	0.0151 (7)	0.0158 (6)	0.0075 (5)	0.0084 (5)	0.0056 (5)
C11	0.0143 (6)	0.0138 (6)	0.0207 (7)	0.0059 (5)	0.0084 (5)	0.0064 (5)
C12	0.0141 (6)	0.0136 (6)	0.0183 (6)	0.0050 (5)	0.0045 (5)	0.0036 (5)
C13	0.0166 (7)	0.0162 (7)	0.0153 (6)	0.0060 (5)	0.0073 (5)	0.0047 (5)
C14	0.0153 (7)	0.0134 (6)	0.0159 (6)	0.0034 (5)	0.0056 (5)	0.0034 (5)
C15	0.0138 (6)	0.0134 (6)	0.0186 (6)	0.0064 (5)	0.0054 (5)	0.0036 (5)
C17	0.0239 (7)	0.0224 (7)	0.0139 (6)	0.0047 (6)	0.0063 (5)	0.0034 (5)
C18	0.0232 (7)	0.0192 (7)	0.0263 (7)	0.0006 (6)	0.0112 (6)	0.0066 (6)
C19	0.0207 (7)	0.0232 (7)	0.0176 (7)	0.0005 (6)	0.0063 (6)	−0.0016 (6)
C20	0.0132 (6)	0.0159 (7)	0.0241 (7)	0.0055 (5)	0.0083 (5)	0.0061 (6)
C21	0.0133 (7)	0.0214 (7)	0.0220 (7)	−0.0010 (6)	0.0027 (5)	0.0033 (6)
C22	0.0264 (8)	0.0184 (7)	0.0273 (8)	0.0003 (6)	0.0105 (6)	0.0033 (6)

Geometric parameters (Å, º) top

S1—C1	1.7040 (14)	C14—C15	1.528 (2)
S1—C4	1.7254 (15)	C14—C20	1.4734 (19)
O1—C5	1.2219 (16)	C21—C22	1.497 (2)
O2—C10	1.3653 (16)	C1—H1	0.9300
O2—C17	1.4303 (17)	C2—H2	0.9300
O3—C11	1.3755 (18)	C3—H3	0.9300
O3—C18	1.4249 (18)	C6—H6A	0.9700
O4—C12	1.3623 (17)	C6—H6B	0.9700
O4—C19	1.4304 (17)	C7—H7	0.9800
O5—C15	1.1996 (17)	C9—H9	0.9300
O6—C15	1.3342 (16)	C13—H13	0.9300
O6—C21	1.4651 (18)	C14—H14	0.9800
N1—C20	1.1397 (19)	C17—H17A	0.9600
C1—C2	1.364 (2)	C17—H17B	0.9600
C2—C3	1.417 (2)	C17—H17C	0.9600
C3—C4	1.368 (2)	C18—H18A	0.9600
C4—C5	1.4679 (19)	C18—H18B	0.9600
C5—C6	1.514 (2)	C18—H18C	0.9600
C6—C7	1.5309 (18)	C19—H19A	0.9600
C7—C8	1.521 (2)	C19—H19B	0.9600
C7—C14	1.559 (2)	C19—H19C	0.9600
C8—C9	1.3913 (18)	C21—H21A	0.9700
C8—C13	1.3941 (19)	C21—H21B	0.9700
C9—C10	1.390 (2)	C22—H22A	0.9600
C10—C11	1.3959 (19)	C22—H22B	0.9600
C11—C12	1.3971 (18)	C22—H22C	0.9600
C12—C13	1.391 (2)

C1—S1—C4	91.52 (7)	C4—C3—H3	124.00
C10—O2—C17	117.05 (11)	C5—C6—H6A	109.00
C11—O3—C18	113.37 (11)	C5—C6—H6B	109.00
C12—O4—C19	117.02 (11)	C7—C6—H6A	109.00
C15—O6—C21	115.87 (11)	C7—C6—H6B	109.00
S1—C1—C2	112.56 (11)	H6A—C6—H6B	108.00
C1—C2—C3	111.94 (13)	C6—C7—H7	107.00
C2—C3—C4	112.82 (13)	C8—C7—H7	107.00
S1—C4—C3	111.16 (11)	C14—C7—H7	107.00
S1—C4—C5	119.12 (10)	C8—C9—H9	120.00
C3—C4—C5	129.71 (13)	C10—C9—H9	120.00
O1—C5—C4	121.25 (13)	C8—C13—H13	120.00
O1—C5—C6	121.58 (12)	C12—C13—H13	120.00
C4—C5—C6	117.12 (11)	C7—C14—H14	109.00
C5—C6—C7	112.22 (11)	C15—C14—H14	109.00
C6—C7—C8	112.13 (11)	C20—C14—H14	109.00
C6—C7—C14	110.99 (11)	O2—C17—H17A	109.00
C8—C7—C14	112.42 (11)	O2—C17—H17B	109.00
C7—C8—C9	118.67 (12)	O2—C17—H17C	109.00
C7—C8—C13	121.01 (12)	H17A—C17—H17B	109.00
C9—C8—C13	120.31 (13)	H17A—C17—H17C	109.00
C8—C9—C10	120.15 (12)	H17B—C17—H17C	109.00
O2—C10—C9	124.82 (12)	O3—C18—H18A	109.00
O2—C10—C11	115.26 (13)	O3—C18—H18B	109.00
C9—C10—C11	119.90 (12)	O3—C18—H18C	109.00
O3—C11—C10	119.50 (12)	H18A—C18—H18B	110.00
O3—C11—C12	120.84 (12)	H18A—C18—H18C	109.00
C10—C11—C12	119.60 (13)	H18B—C18—H18C	109.00
O4—C12—C11	115.00 (12)	O4—C19—H19A	109.00
O4—C12—C13	124.50 (12)	O4—C19—H19B	109.00
C11—C12—C13	120.51 (12)	O4—C19—H19C	109.00
C8—C13—C12	119.43 (12)	H19A—C19—H19B	109.00
C7—C14—C15	109.30 (11)	H19A—C19—H19C	109.00
C7—C14—C20	111.98 (11)	H19B—C19—H19C	110.00
C15—C14—C20	109.62 (11)	O6—C21—H21A	109.00
O5—C15—O6	125.34 (13)	O6—C21—H21B	109.00
O5—C15—C14	124.81 (12)	C22—C21—H21A	109.00
O6—C15—C14	109.74 (11)	C22—C21—H21B	109.00
N1—C20—C14	177.91 (16)	H21A—C21—H21B	108.00
O6—C21—C22	111.19 (12)	C21—C22—H22A	109.00
S1—C1—H1	124.00	C21—C22—H22B	109.00
C2—C1—H1	124.00	C21—C22—H22C	110.00
C1—C2—H2	124.00	H22A—C22—H22B	109.00
C3—C2—H2	124.00	H22A—C22—H22C	109.00
C2—C3—H3	124.00	H22B—C22—H22C	109.00

C4—S1—C1—C2	0.13 (13)	C14—C7—C8—C9	100.64 (14)
C1—S1—C4—C3	−0.09 (13)	C14—C7—C8—C13	−80.57 (15)
C1—S1—C4—C5	179.01 (12)	C6—C7—C14—C15	63.27 (13)
C17—O2—C10—C9	−1.2 (2)	C6—C7—C14—C20	−58.39 (15)
C17—O2—C10—C11	−179.64 (12)	C8—C7—C14—C15	−170.23 (10)
C18—O3—C11—C10	−101.99 (15)	C8—C7—C14—C20	68.11 (14)
C18—O3—C11—C12	81.04 (16)	C7—C8—C9—C10	176.92 (12)
C19—O4—C12—C11	−168.81 (12)	C13—C8—C9—C10	−1.9 (2)
C19—O4—C12—C13	12.0 (2)	C7—C8—C13—C12	−177.12 (12)
C21—O6—C15—O5	−1.1 (2)	C9—C8—C13—C12	1.7 (2)
C21—O6—C15—C14	−177.57 (11)	C8—C9—C10—O2	−178.97 (13)
C15—O6—C21—C22	82.45 (15)	C8—C9—C10—C11	−0.6 (2)
S1—C1—C2—C3	−0.14 (17)	O2—C10—C11—O3	4.74 (19)
C1—C2—C3—C4	0.1 (2)	O2—C10—C11—C12	−178.24 (12)
C2—C3—C4—S1	0.03 (18)	C9—C10—C11—O3	−173.80 (13)
C2—C3—C4—C5	−178.95 (15)	C9—C10—C11—C12	3.2 (2)
S1—C4—C5—O1	5.0 (2)	O3—C11—C12—O4	−5.74 (19)
S1—C4—C5—C6	−172.23 (10)	O3—C11—C12—C13	173.52 (13)
C3—C4—C5—O1	−176.11 (16)	C10—C11—C12—O4	177.29 (12)
C3—C4—C5—C6	6.7 (2)	C10—C11—C12—C13	−3.5 (2)
O1—C5—C6—C7	27.39 (19)	O4—C12—C13—C8	−179.79 (13)
C4—C5—C6—C7	−155.42 (12)	C11—C12—C13—C8	1.0 (2)
C5—C6—C7—C8	67.74 (14)	C7—C14—C15—O5	−100.86 (16)
C5—C6—C7—C14	−165.60 (11)	C7—C14—C15—O6	75.65 (13)
C6—C7—C8—C9	−133.47 (13)	C20—C14—C15—O5	22.22 (19)
C6—C7—C8—C13	45.31 (17)	C20—C14—C15—O6	−161.28 (11)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1ⁱ	0.93	2.49	3.368 (2)	157
C18—H18B···O2ⁱⁱ	0.96	2.56	3.385 (2)	143
C17—H17A···Cg2ⁱⁱⁱ	0.96	2.85	3.6327 (16)	139

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₃NO₆S
M_r	417.47
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.4308 (5), 10.5025 (6), 12.3059 (6)
α, β, γ (°)	98.530 (2), 107.950 (2), 97.966 (3)
V (Å³)	1005.26 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.22 × 0.20 × 0.19

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16712, 3965, 3498
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.080, 1.04
No. of reflections	3965
No. of parameters	266
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.29

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1ⁱ	0.93	2.49	3.368 (2)	157
C18—H18B···O2ⁱⁱ	0.96	2.56	3.385 (2)	143
C17—H17A···Cg2ⁱⁱⁱ	0.96	2.85	3.6327 (16)	139

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

Acknowledgements

SMK thanks the UGC–BRS and the University of Mysore for the award of a fellowship.

References

Günther, O. S. & Steinmetz, R. (1963). Liebigs Ann. Chem. 668, 19–30. Google Scholar
Harrison, W. T. A., Chidan Kumar, C. S., Yathirajan, H. S., Ashalatha, B. V. & Narayana, B. (2010). Acta Cryst. E66, o2477. Web of Science CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 12| December 2012| Page o3275

doi:10.1107/S1600536812044522

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

Ethyl 2-cyano-5-oxo-5-(thio­phen-2-yl)-3-(3,4,5-trimeth­­oxy­phen­yl)penta­noate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 2-cyano-5-oxo-5-(thiophen-2-yl)-3-(3,4,5-trimethoxyphenyl)pentanoate