(1RS,6SR)-Ethyl 4,6-bis-(4-fluoro-phen-yl)-2-oxocyclo-hex-3-ene-1-carboxyl-ate.

In the crystal structure of the title compound, C(21)H(18)F(2)O(3), the cyclo-hexene 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 cyclo-hexenone 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 inter-molecular C-H⋯O, C-H⋯F and C-H⋯π inter-actions join mol-ecules 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 = 356.35

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.168

S = 1.11

3926 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H18F2O3	F(000) = 744
Mr = 356.35	Dx = 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

Oxford Diffraction Xcalibur Sapphire2 diffractometer	3926 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2590 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 8.1929 pixels mm-1	θmax = 28.2°, θmin = 2.9°
ω–scan	h = −14→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −15→14
Tmin = 0.947, Tmax = 1.000	l = −16→17
14582 measured reflections

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(Fo2) + (0.0925P)2 + 0.1094P] where P = (Fo2 + 2Fc2)/3
3926 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···Cg1iv	0.98	2.76	3.653 (3)	152

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⋯Cg1iv	0.98	2.76	3.653 (3)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .