(1RS,6SR)-Ethyl 4,6-bis­(4-fluoro­phen­yl)-2-oxocyclo­hex-3-ene-1-carboxyl­ate

Dutkiewicz, G.; Narayana, B.; Veena, K.; Yathirajan, H.S.; Kubicki, M.

doi:10.1107/S1600536811000171

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o336

doi:10.1107/S1600536811000171

Open

access

(1RS,6SR)-Ethyl 4,6-bis(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate

Grzegorz Dutkiewicz,^a B. Narayana,^b K. Veena,^b H. S. Yathirajan ^c and Maciej Kubicki ^a ^*

^aDepartment of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574199, India, and ^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: mkubicki@amu.edu.pl

(Received 29 December 2010; accepted 4 January 2011; online 12 January 2011)

In the crystal structure of the title compound, C₂₁H₁₈F₂O₃, the cyclohexene ring has a slightly distorted sofa conformation; the two benzene rings are inclined by 76.27 (8)° and their planes make dihedral angles of 16.65 (10) and 67.53 (7)° with the approximately planar part of the cyclohexenone ring [maximum deviation 0.044 (2) Å, while the sixth atom is displaced by 0.648 (3) Å from this plane]. In the crystal, weak intermolecular C—H⋯O, C—H⋯F and C—H⋯π interactions join molecules into a three-dimensional structure.

Related literature

For some biological applications of cyclohexanones, see: Li & Strobel (2001 ). For general properties, see: Jung (1991 ); Tabba et al. (1995 ). For asymmetry parameters, see: Duax & Norton (1975 ). For related structures, see: Anuradha et al. (2009 ); Li et al. (2009 ); Fun et al. (2008 , 2009 , 2010 ); Badshah et al. (2009 ).

Experimental

Crystal data

C₂₁H₁₈F₂O₃
M_r = 356.35
Monoclinic, P 2₁ /n
a = 11.062 (2) Å
b = 11.675 (3) Å
c = 13.854 (3) Å
β = 92.89 (2)°
V = 1787.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.45 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.947, T_max = 1.000
14582 measured reflections
3926 independent reflections
2590 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.168
S = 1.11
3926 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C46—H46⋯O12ⁱ	0.93	2.56	3.244 (3)	130
C5—H52⋯F64ⁱⁱ	0.97	2.49	3.278 (2)	138
C5—H51⋯F44ⁱⁱⁱ	0.97	2.54	3.484 (2)	165
C1—H1⋯Cg1^iv	0.98	2.76	3.653 (3)	152
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+2, -y, -z+1; (iii) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x+2, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000171/dn2648sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000171/dn2648Isup2.hkl

checkCIF report

Comment top

An important feature of chalcones and their heteroanalogs is the ability to act as activated unsaturated systems in conjugated addition reactions of carbanions in the presence of basic catalysts ( Jung, 1991). This type of reaction may be exploited with the view of obtaining highly functionalized cyclohexene derivatives (Tabba et al., 1995). Cyclohexenone derivatives possess a wide variety of biological activities, e.g. they were reported to have fungicidal and antitumor activities (Li & Strobel, 2001). Structures of some similar compounds have been reported earlier (for instance, ethyl 6-(4-chlorophenyl)-4-(4-methoxyphenyl)- 2-oxocyclohex-3-ene-1- carboxylate, Fun et al., 2009, ethyl 4-(4-methoxyphenyl)-2-oxo-6- phenylcyclohex-3-ene-1-carboxylate, Fun et al., 2008, ethyl 4-(4-bromophenyl)-6-(4-ethoxyphenyl)- 2-oxocyclohex-3-enecarboxylate, Badshah et al., 2009, ethyl 6 - r-(2-chlorophenyl)-2-oxo-4- phenylcyclohex-3-ene-1 - t-carboxylate (Anuradha et al., 2009). In the course of our studies on chalcone derivatives, we have synthesized some cyclohexene derivatives. here we report the crystal structure of (1RS,6SR) ethyl 4,6-bis(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate (I, Scheme 1).

In I, the cyclohexene ring adopts slightly distorted sofa conformation (Fig. 1), the asymmetry parameter ΔC_s³ (Duax & Norton, 1975) is 7.8°. This is also confirmed by least-squares calculations: five atoms C1 - C5 are almost coplanar, maximum deviation is 0.044 (2) Å, while the sixth atom, C6, is by 0.648 (3)Å out of this mean plane. The presence of two largest peaks at the difference Fourier map of ca 0.5 e.Å^-3 (more than two times larger than the next peak) close to C1 and C6 atoms suggests the possibility of slight disorder of these two carbon atoms; this kind of disorder was observed previously in similar structures (e.g. Li et al., 2009; Fun et al., 2010)

The overall conformation of I (cf. Fig. 1) can be characterized by the dihedral angles between the phenyl rings, of 76.27 (8)°, and between these rings and the plane of cyclohexene ring which are equal to 16.65 (10)° for the ring at position 4 of the cyclohexene (i.e. next to the double bond) and 67.53 (7)° for fluorophenyl ring at position 6. In the crystal of the methyl analogue, methyl 4,6-bis(4-fluorophenyl)-2-oxocyclohex- 3-ene-1-carboxylate (Fun et al., 2010) there are two symmetry independent molecules, but the overall conformation of both of them is similar to that of I. The dihedral angles between fluorophenyl rings are 79.7 (2)° and 73.7 (2)°, and the angles between the cyclohexene plane and the fluorophenyl rings at position 4 are 14.9° and 29.9°, while those at 6-postion: 73.7° and 84.0°. In the structure of ethyl 4-(4-bromophenyl)-6-(4-ethoxyphenyl)-2-oxo-4- phenylcyclohex-3-enecarboxylate (Badshah et al., 2009) appropriate angles are 81.73 (12)°. 13.8 (3)° and 88.44 (17)°.

In the crystal structure the molecules are joined by weak C—H···O, C—H···F and C—H···πl interactions (Fig. 2).

Related literature top

For some biological applications of cyclohexanones, see: Li & Strobel (2001). For general properties, see: Jung (1991); Tabba et al. (1995). For asymmetry parameters, see: Duax & Norton (1975). For related structures, see: Anuradha et al. (2009); Li et al. (2009); Fun et al. (2008, 2009, 2010); Badshah et al. (2009).

Experimental top

A mixture of (2E)-1,3-bis(4-fluorophenyl)prop-2-en-1-one (0.01 mol) and ethyl acetoacetate (0.01 mol) were refluxed for 2 hr in 10–15 ml of ethanol in the presence of 0.8 ml 10% NaOH. The crystals were obtained by a slow evaporation from toluene solution. C₂₁H₁₈F₂O_3, C: 70.71(70.78%); H: 5.07(5.09%); M.P-367 K.

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: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Anisotropic ellipsoid representation of the components of I together with atom labelling scheme. The ellipsoids are drawn at 50% probability level, hydrogen atoms are depicted as spheres with arbitrary radii.
	Fig. 2. The crystal packing as seen along x-direction. Weak interactions (cf. text) are shown as dashed lines.

(1RS,6SR)-Ethyl 4,6-bis(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate top

Crystal data top

C₂₁H₁₈F₂O₃	F(000) = 744
M_r = 356.35	D_x = 1.325 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6918 reflections
a = 11.062 (2) Å	θ = 2.9–28.1°
b = 11.675 (3) Å	µ = 0.10 mm⁻¹
c = 13.854 (3) Å	T = 295 K
β = 92.89 (2)°	Block, colourless
V = 1787.0 (7) Å³	0.45 × 0.2 × 0.2 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	3926 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2590 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 8.1929 pixels mm^-1	θ_max = 28.2°, θ_min = 2.9°
ω–scan	h = −14→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −15→14
T_min = 0.947, T_max = 1.000	l = −16→17
14582 measured 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0925P)² + 0.1094P] where P = (F_o² + 2F_c²)/3
3926 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₁H₁₈F₂O₃	V = 1787.0 (7) Å³
M_r = 356.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.062 (2) Å	µ = 0.10 mm⁻¹
b = 11.675 (3) Å	T = 295 K
c = 13.854 (3) Å	0.45 × 0.2 × 0.2 mm
β = 92.89 (2)°

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	3926 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2590 reflections with I > 2σ(I)
T_min = 0.947, T_max = 1.000	R_int = 0.021
14582 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 1.11	Δρ_max = 0.60 e Å⁻³
3926 reflections	Δρ_min = −0.24 e Å⁻³
235 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	0.74323 (18)	0.34723 (16)	0.44006 (15)	0.0454 (5)
H1	0.7716	0.3445	0.5082	0.054*
C11	0.61584 (18)	0.29820 (17)	0.43248 (16)	0.0454 (5)
O12	0.55538 (16)	0.28780 (15)	0.35870 (12)	0.0687 (5)
O13	0.58204 (14)	0.26686 (13)	0.51815 (11)	0.0580 (4)
C14	0.4670 (2)	0.2089 (2)	0.5236 (2)	0.0717 (7)
H142	0.4485	0.1662	0.4647	0.086*
H141	0.4029	0.2642	0.5320	0.086*
C15	0.4771 (4)	0.1311 (4)	0.6066 (3)	0.1367 (17)
H153	0.4018	0.0914	0.6125	0.205*
H152	0.4956	0.1743	0.6645	0.205*
H151	0.5404	0.0765	0.5974	0.205*
C2	0.74302 (18)	0.47139 (15)	0.40859 (14)	0.0419 (5)
O2	0.65172 (14)	0.52929 (12)	0.41192 (11)	0.0585 (4)
C3	0.85742 (17)	0.51786 (15)	0.37999 (14)	0.0405 (5)
H3	0.8608	0.5956	0.3659	0.049*
C4	0.95848 (16)	0.45610 (14)	0.37261 (12)	0.0338 (4)
C41	1.07396 (16)	0.50657 (15)	0.34287 (12)	0.0360 (4)
C42	1.18418 (18)	0.45216 (16)	0.36282 (14)	0.0431 (5)
H42	1.1856	0.3826	0.3956	0.052*
C43	1.2921 (2)	0.49924 (19)	0.33490 (16)	0.0525 (5)
H43	1.3656	0.4629	0.3494	0.063*
C44	1.2873 (2)	0.60004 (19)	0.28573 (15)	0.0533 (6)
F44	1.39211 (13)	0.64622 (13)	0.25678 (11)	0.0824 (5)
C45	1.1821 (2)	0.6560 (2)	0.26431 (16)	0.0609 (6)
H45	1.1820	0.7250	0.2309	0.073*
C46	1.0748 (2)	0.60919 (17)	0.29278 (15)	0.0508 (5)
H46	1.0022	0.6471	0.2781	0.061*
C5	0.95652 (16)	0.32986 (14)	0.39434 (14)	0.0381 (4)
H52	0.9885	0.3175	0.4600	0.046*
H51	1.0091	0.2906	0.3512	0.046*
C6	0.82998 (18)	0.27777 (15)	0.38320 (15)	0.0440 (5)
H6	0.8035	0.2847	0.3149	0.053*
C61	0.83451 (16)	0.15033 (15)	0.40669 (15)	0.0417 (5)
C62	0.8266 (2)	0.10661 (18)	0.49880 (16)	0.0557 (6)
H62	0.8161	0.1562	0.5502	0.067*
C63	0.8341 (2)	−0.0113 (2)	0.51561 (18)	0.0629 (6)
H63	0.8284	−0.0411	0.5775	0.075*
C64	0.8499 (2)	−0.08081 (17)	0.4390 (2)	0.0567 (6)
F64	0.85470 (16)	−0.19620 (11)	0.45443 (14)	0.0970 (6)
C65	0.8613 (2)	−0.04147 (17)	0.34810 (19)	0.0593 (6)
H65	0.8746	−0.0914	0.2974	0.071*
C66	0.85233 (19)	0.07498 (16)	0.33294 (16)	0.0491 (5)
H66	0.8586	0.1033	0.2707	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0443 (11)	0.0402 (11)	0.0518 (12)	0.0010 (8)	0.0040 (9)	0.0007 (9)
C11	0.0393 (11)	0.0390 (10)	0.0576 (14)	0.0033 (8)	0.0016 (10)	−0.0015 (9)
O12	0.0698 (12)	0.0782 (12)	0.0573 (10)	−0.0158 (9)	−0.0052 (9)	−0.0040 (8)
O13	0.0470 (9)	0.0678 (10)	0.0592 (10)	−0.0111 (7)	0.0014 (7)	0.0059 (8)
C14	0.0485 (14)	0.0813 (17)	0.0861 (18)	−0.0126 (12)	0.0113 (13)	0.0076 (14)
C15	0.122 (3)	0.164 (4)	0.122 (3)	−0.078 (3)	−0.019 (2)	0.057 (3)
C2	0.0448 (11)	0.0346 (10)	0.0462 (11)	0.0060 (8)	0.0004 (9)	−0.0021 (8)
O2	0.0509 (9)	0.0459 (8)	0.0795 (11)	0.0148 (7)	0.0093 (8)	0.0028 (7)
C3	0.0488 (12)	0.0242 (8)	0.0483 (11)	0.0018 (8)	0.0000 (9)	0.0004 (8)
C4	0.0424 (10)	0.0291 (9)	0.0297 (9)	−0.0012 (7)	0.0005 (7)	−0.0009 (7)
C41	0.0451 (11)	0.0296 (9)	0.0334 (10)	−0.0040 (8)	0.0028 (8)	−0.0023 (7)
C42	0.0467 (11)	0.0351 (9)	0.0478 (12)	−0.0016 (8)	0.0057 (9)	−0.0003 (8)
C43	0.0462 (12)	0.0543 (12)	0.0578 (13)	−0.0023 (10)	0.0113 (10)	−0.0058 (11)
C44	0.0573 (14)	0.0563 (13)	0.0480 (12)	−0.0163 (11)	0.0189 (10)	−0.0014 (10)
F44	0.0719 (10)	0.0901 (11)	0.0885 (10)	−0.0272 (8)	0.0355 (8)	0.0064 (8)
C45	0.0766 (17)	0.0492 (12)	0.0581 (14)	−0.0137 (12)	0.0132 (12)	0.0146 (11)
C46	0.0587 (13)	0.0440 (11)	0.0499 (12)	−0.0008 (9)	0.0046 (10)	0.0142 (9)
C5	0.0398 (10)	0.0301 (9)	0.0450 (11)	0.0022 (7)	0.0073 (8)	0.0018 (8)
C6	0.0482 (12)	0.0328 (10)	0.0512 (12)	0.0010 (8)	0.0048 (9)	0.0011 (8)
C61	0.0360 (10)	0.0313 (9)	0.0581 (13)	−0.0032 (7)	0.0061 (9)	0.0024 (9)
C62	0.0621 (14)	0.0476 (12)	0.0579 (14)	−0.0016 (10)	0.0069 (11)	−0.0028 (10)
C63	0.0655 (16)	0.0566 (14)	0.0661 (16)	−0.0028 (11)	−0.0015 (11)	0.0240 (12)
C64	0.0511 (13)	0.0287 (10)	0.0884 (18)	−0.0007 (9)	−0.0142 (11)	0.0060 (11)
F64	0.1057 (13)	0.0316 (7)	0.1500 (15)	0.0013 (7)	−0.0293 (11)	0.0191 (8)
C65	0.0605 (15)	0.0387 (11)	0.0777 (17)	0.0028 (10)	−0.0064 (12)	−0.0118 (11)
C66	0.0511 (12)	0.0362 (10)	0.0597 (13)	−0.0016 (9)	0.0014 (10)	−0.0003 (9)

Geometric parameters (Å, º) top

C1—C6	1.508 (3)	C43—C44	1.359 (3)
C1—C2	1.514 (3)	C43—H43	0.9300
C1—C11	1.520 (3)	C44—C45	1.354 (3)
C1—H1	0.9800	C44—F44	1.358 (2)
C11—O12	1.199 (2)	C45—C46	1.382 (3)
C11—O13	1.314 (2)	C45—H45	0.9300
O13—C14	1.446 (3)	C46—H46	0.9300
C14—C15	1.466 (4)	C5—C6	1.527 (3)
C14—H142	0.9700	C5—H52	0.9700
C14—H141	0.9700	C5—H51	0.9700
C15—H153	0.9600	C6—C61	1.523 (2)
C15—H152	0.9600	C6—H6	0.9800
C15—H151	0.9600	C61—C66	1.370 (3)
C2—O2	1.218 (2)	C61—C62	1.381 (3)
C2—C3	1.450 (3)	C62—C63	1.398 (3)
C3—C4	1.339 (3)	C62—H62	0.9300
C3—H3	0.9300	C63—C64	1.354 (3)
C4—C41	1.484 (2)	C63—H63	0.9300
C4—C5	1.505 (2)	C64—C65	1.352 (3)
C41—C46	1.385 (3)	C64—F64	1.365 (2)
C41—C42	1.390 (3)	C65—C66	1.379 (3)
C42—C43	1.387 (3)	C65—H65	0.9300
C42—H42	0.9300	C66—H66	0.9300

C6—C1—C2	110.86 (16)	C45—C44—F44	118.8 (2)
C6—C1—C11	111.93 (17)	C45—C44—C43	122.6 (2)
C2—C1—C11	110.66 (16)	F44—C44—C43	118.6 (2)
C6—C1—H1	107.7	C44—C45—C46	119.2 (2)
C2—C1—H1	107.7	C44—C45—H45	120.4
C11—C1—H1	107.7	C46—C45—H45	120.4
O12—C11—O13	124.74 (19)	C45—C46—C41	120.8 (2)
O12—C11—C1	124.9 (2)	C45—C46—H46	119.6
O13—C11—C1	110.33 (18)	C41—C46—H46	119.6
C11—O13—C14	117.95 (18)	C4—C5—C6	113.10 (15)
O13—C14—C15	107.4 (2)	C4—C5—H52	109.0
O13—C14—H142	110.2	C6—C5—H52	109.0
C15—C14—H142	110.2	C4—C5—H51	109.0
O13—C14—H141	110.2	C6—C5—H51	109.0
C15—C14—H141	110.2	H52—C5—H51	107.8
H142—C14—H141	108.5	C1—C6—C61	115.37 (16)
C14—C15—H153	109.5	C1—C6—C5	109.70 (16)
C14—C15—H152	109.5	C61—C6—C5	110.32 (15)
H153—C15—H152	109.5	C1—C6—H6	107.0
C14—C15—H151	109.5	C61—C6—H6	107.0
H153—C15—H151	109.5	C5—C6—H6	107.0
H152—C15—H151	109.5	C66—C61—C62	118.03 (18)
O2—C2—C3	122.63 (17)	C66—C61—C6	118.18 (18)
O2—C2—C1	120.65 (17)	C62—C61—C6	123.74 (18)
C3—C2—C1	116.63 (16)	C61—C62—C63	120.8 (2)
C4—C3—C2	124.26 (17)	C61—C62—H62	119.6
C4—C3—H3	117.9	C63—C62—H62	119.6
C2—C3—H3	117.9	C64—C63—C62	117.9 (2)
C3—C4—C41	122.77 (16)	C64—C63—H63	121.0
C3—C4—C5	119.46 (16)	C62—C63—H63	121.0
C41—C4—C5	117.76 (15)	C65—C64—C63	123.24 (19)
C46—C41—C42	117.85 (17)	C65—C64—F64	118.5 (2)
C46—C41—C4	120.67 (17)	C63—C64—F64	118.3 (2)
C42—C41—C4	121.47 (16)	C64—C65—C66	117.9 (2)
C43—C42—C41	121.47 (19)	C64—C65—H65	121.1
C43—C42—H42	119.3	C66—C65—H65	121.1
C41—C42—H42	119.3	C61—C66—C65	122.1 (2)
C44—C43—C42	118.0 (2)	C61—C66—H66	118.9
C44—C43—H43	121.0	C65—C66—H66	118.9
C42—C43—H43	121.0

C6—C1—C11—O12	−60.8 (3)	C44—C45—C46—C41	0.2 (3)
C2—C1—C11—O12	63.4 (3)	C42—C41—C46—C45	−0.4 (3)
C6—C1—C11—O13	118.10 (19)	C4—C41—C46—C45	−179.49 (18)
C2—C1—C11—O13	−117.69 (18)	C3—C4—C5—C6	23.3 (2)
O12—C11—O13—C14	4.2 (3)	C41—C4—C5—C6	−156.25 (16)
C1—C11—O13—C14	−174.69 (18)	C2—C1—C6—C61	−178.09 (16)
C11—O13—C14—C15	149.6 (3)	C11—C1—C6—C61	−54.0 (2)
C6—C1—C2—O2	148.72 (19)	C2—C1—C6—C5	56.6 (2)
C11—C1—C2—O2	23.9 (3)	C11—C1—C6—C5	−179.31 (16)
C6—C1—C2—C3	−34.5 (2)	C4—C5—C6—C1	−51.6 (2)
C11—C1—C2—C3	−159.36 (17)	C4—C5—C6—C61	−179.72 (15)
O2—C2—C3—C4	−177.82 (19)	C1—C6—C61—C66	144.90 (19)
C1—C2—C3—C4	5.5 (3)	C5—C6—C61—C66	−90.1 (2)
C2—C3—C4—C41	179.85 (16)	C1—C6—C61—C62	−37.8 (3)
C2—C3—C4—C5	0.3 (3)	C5—C6—C61—C62	87.2 (2)
C3—C4—C41—C46	−20.5 (3)	C66—C61—C62—C63	−1.3 (3)
C5—C4—C41—C46	159.02 (18)	C6—C61—C62—C63	−178.6 (2)
C3—C4—C41—C42	160.47 (18)	C61—C62—C63—C64	0.3 (3)
C5—C4—C41—C42	−20.0 (2)	C62—C63—C64—C65	1.4 (3)
C46—C41—C42—C43	0.9 (3)	C62—C63—C64—F64	−178.6 (2)
C4—C41—C42—C43	179.90 (17)	C63—C64—C65—C66	−2.1 (4)
C41—C42—C43—C44	−1.0 (3)	F64—C64—C65—C66	177.94 (19)
C42—C43—C44—C45	0.8 (3)	C62—C61—C66—C65	0.6 (3)
C42—C43—C44—F44	−179.08 (18)	C6—C61—C66—C65	178.04 (19)
F44—C44—C45—C46	179.47 (18)	C64—C65—C66—C61	1.0 (3)
C43—C44—C45—C46	−0.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C46—H46···O12ⁱ	0.93	2.56	3.244 (3)	130
C5—H52···F64ⁱⁱ	0.97	2.49	3.278 (2)	138
C5—H51···F44ⁱⁱⁱ	0.97	2.54	3.484 (2)	165
C1—H1···Cg1^iv	0.98	2.76	3.653 (3)	152

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+2, −y, −z+1; (iii) −x+5/2, y−1/2, −z+1/2; (iv) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈F₂O₃
M_r	356.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	11.062 (2), 11.675 (3), 13.854 (3)
β (°)	92.89 (2)
V (Å³)	1787.0 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.45 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire2 diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.947, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14582, 3926, 2590
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.664

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.168, 1.11
No. of reflections	3926
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.24

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C46—H46···O12ⁱ	0.93	2.56	3.244 (3)	130
C5—H52···F64ⁱⁱ	0.97	2.49	3.278 (2)	138
C5—H51···F44ⁱⁱⁱ	0.97	2.54	3.484 (2)	165
C1—H1···Cg1^iv	0.98	2.76	3.653 (3)	152

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+2, −y, −z+1; (iii) −x+5/2, y−1/2, −z+1/2; (iv) −x+2, −y+1, −z+1.

Acknowledgements

BN thanks the UGC and DST for financial assistance under the SAP and FIST programmes. HSY thanks the UOM for sabbatical leave.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Anuradha, N., Thiruvalluvar, A., Pandiarajan, K. & Yuvaraj, C. (2009). Acta Cryst. E65, o191. Web of Science CSD CrossRef IUCr Journals Google Scholar
Badshah, A., Hasan, A. & Barbarín, C. R. (2009). Acta Cryst. E65, o467. Web of Science CSD CrossRef IUCr Journals Google Scholar
Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, pp. 16–22. New York: Plenum. Google Scholar
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o864–o865. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Fun, H.-K., Jebas, S. R., Girish, K. S. & Kalluraya, B. (2009). Acta Cryst. E65, o1235. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Jebas, S. R., Rao, J. N. & Kalluraya, B. (2008). Acta Cryst. E64, o2448. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jung, M. E. (1991). Comprehensive Organic Synthesis, Vol. 4, edited by B. M. Trost, I. Fleming & M. F. Semmelhack, pp. 1–68. Oxford: Pergamon Press: Oxford. Google Scholar
Li, H., Mayekar, A. N., Narayana, B., Yathirajan, H. S. & Harrison, W. T. A. (2009). Acta Cryst. E65, o1186. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, J. Y. & Strobel, G. A. (2001). Phytochemistry, 57, 261–265. Web of Science CrossRef PubMed CAS Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tabba, H. D., Yousef, N. M. & Al-Arab, M. M. (1995). Coll. Czech. Chem. Commun. 60, 594–604. CSD CrossRef CAS Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o336

doi:10.1107/S1600536811000171

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

(1RS,6SR)-Ethyl 4,6-bis­­(4-fluoro­phen­yl)-2-oxo­cyclo­hex-3-ene-1-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1RS,6SR)-Ethyl 4,6-bis(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate