5-(4-Chloro­phen­yl)-1-cyclo­propyl-2-(2-fluoro­phen­yl)-3-phenyl­pentane-1,5-dione

Srinivasan, T.; Senthilkumar, G.; Manikandan, H.; Neelakandan, K.; Velmurugan, D.

doi:10.1107/S1600536813001074

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o252

doi:10.1107/S1600536813001074

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5-(4-Chlorophenyl)-1-cyclopropyl-2-(2-fluorophenyl)-3-phenylpentane-1,5-dione

Thothadri Srinivasan,^a Govindaraj Senthilkumar,^b Haridoss Manikandan,^b Kaliaperumal Neelakandan ^b and Devadasan Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, Tamilnadu, India
^*Correspondence e-mail: shirai2011@gmail.com

(Received 4 January 2013; accepted 11 January 2013; online 19 January 2013)

In the title compound, C₂₆H₂₂ClFO₂, the cyclopropane ring makes dihedral angles of 45.7 (2), 49.0 (2) and 65.2 (2)° with the fluoro-substituted phenyl ring, the benzene ring and the chloro-substituted phenyl ring, respectively. The F and Cl atoms deviate by 0.0307 (11) and 0.0652 (6) Å, respectively, from the planes of the phenyl rings to which they are attached. In the crystal, molecules are linked by C—H⋯F hydrogen bonds, forming chains along the b axis.

Related literature

For the uses and biological importance of diketones, see: Bennett et al. (1999 ); Sato et al. (2008 ). For a related structure, see: Li et al. (2008 ).

Experimental

Crystal data

C₂₆H₂₂ClFO₂
M_r = 420.89
Monoclinic, C 2/c
a = 43.0465 (15) Å
b = 5.7257 (2) Å
c = 18.2828 (6) Å
β = 109.103 (2)°
V = 4258.0 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.940, T_max = 0.960
20606 measured reflections
5308 independent reflections
3857 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.146
S = 1.02
5308 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯F1ⁱ	0.98	2.54	3.433 (2)	151
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813001074/su2549sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813001074/su2549Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813001074/su2549Isup3.cml

checkCIF report

Comment top

Diketones are popular in organic synthesis for their applications in biology and medicine. They are known to exhibit antioxidant, antitumour and antibacterial activities (Bennett et al., 1999). They are also key intermediates in the preparation of various heterocyclic compounds (Sato et al., 2008). We report herein on the synthesis and crystal structure of one the title diketone.

In the title compound, Fig.1, the cyclopropane ring (C1-C3) makes a dihedral angle of 45.7 (2)° with the fluoro substituted phenyl ring (C6-C11). It makes a dihedral angle of 49.0 (2)° with the unsubstituted phenyl ring (C13-C18) and a dihedral angle of 65.2 (2)° with the chloro substituted phenyl ring (C21-C26). The fluorine atom, F1, deviates by 0.0307 (11) Å from the phenyl ring to which it is attached.

The dihedral angle between the unsubstituted phenyl ring and the fluoro substituted phenyl ring is 3.65 (8)° and the dihedral angle between the unsubstituted phenyl ring and the chloro substituted phenyl ring is 71.73 (8)°. The dihedral angle between the fluoro substituted phenyl ring and the chloro substituted phenyl ring is 71.15 (8)°. The chloro atom, Cl1, deviates by 0.0652 (6) Å from the phenyl ring to which it is attached.

In the crystal, C–H···F hydrogen bonds link the molecules to form chains along the b axis (Table 1 and Fig. 2).

Related literature top

For the uses and biological importance of diketones, see: Bennett et al. (1999); Sato et al. (2008). For a related structure, see: Li et al. (2008).

Experimental top

A mixture of 4-chloroacetophenone(0.01mole), benzaldehyde (0.01 mole), cyclopropyl 2-fluorobenzyl ketone (0.01 mole) and sodium hydroxide solution (10 ml, 10%) in ethanol (50 ml) was stirred for 3 hrs at room temperature. The solid that separated was filtered and washed with distilled water. The product was recrystallised from ethanol [Yield = 95%, M.p. = 405 - 407 K] giving block-like colourless crystals of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the b axis. H-atoms not involved in C-H···F hydrogen bonds (dashed lines) have been excluded for clarity.

5-(4-Chlorophenyl)-1-cyclopropyl-2-(2-fluorophenyl)-3-phenylpentane-1,5-dione top

Crystal data top

C₂₆H₂₂ClFO₂	F(000) = 1760
M_r = 420.89	D_x = 1.313 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5308 reflections
a = 43.0465 (15) Å	θ = 2.0–28.3°
b = 5.7257 (2) Å	µ = 0.21 mm⁻¹
c = 18.2828 (6) Å	T = 293 K
β = 109.103 (2)°	Block, colourless
V = 4258.0 (3) Å³	0.30 × 0.25 × 0.20 mm
Z = 8

Data collection top

Bruker SMART APEXII area-detector diffractometer	5308 independent reflections
Radiation source: fine-focus sealed tube	3857 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and ϕ scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −56→55
T_min = 0.940, T_max = 0.960	k = −7→7
20606 measured reflections	l = −24→24

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0784P)² + 1.3969P] where P = (F_o² + 2F_c²)/3
5308 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₂₆H₂₂ClFO₂	V = 4258.0 (3) Å³
M_r = 420.89	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 43.0465 (15) Å	µ = 0.21 mm⁻¹
b = 5.7257 (2) Å	T = 293 K
c = 18.2828 (6) Å	0.30 × 0.25 × 0.20 mm
β = 109.103 (2)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	5308 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3857 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.960	R_int = 0.026
20606 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.02	Δρ_max = 0.28 e Å⁻³
5308 reflections	Δρ_min = −0.41 e Å⁻³
271 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.98198 (5)	0.1534 (5)	0.63987 (11)	0.0788 (6)
H1A	0.9788	0.3107	0.6558	0.095*
H1B	0.9869	0.0376	0.6808	0.095*
C2	0.99781 (5)	0.1272 (5)	0.58082 (13)	0.0856 (7)
H2A	1.0125	−0.0047	0.5853	0.103*
H2B	1.0044	0.2683	0.5604	0.103*
C3	0.96139 (4)	0.0774 (4)	0.55940 (10)	0.0638 (4)
H3	0.9545	−0.0866	0.5525	0.077*
C4	0.93845 (4)	0.2511 (3)	0.51216 (9)	0.0519 (4)
C5	0.90431 (4)	0.1631 (3)	0.46517 (8)	0.0431 (3)
H5	0.9066	0.0034	0.4482	0.052*
C6	0.88405 (4)	0.1533 (3)	0.51978 (8)	0.0438 (3)
C7	0.88474 (4)	0.3324 (3)	0.57192 (8)	0.0528 (4)
H7	0.8982	0.4612	0.5744	0.063*
C8	0.86572 (5)	0.3224 (3)	0.62019 (10)	0.0614 (4)
H8	0.8667	0.4431	0.6549	0.074*
C9	0.84548 (5)	0.1340 (3)	0.61672 (10)	0.0637 (5)
H9	0.8328	0.1277	0.6492	0.076*
C10	0.84387 (5)	−0.0456 (3)	0.56527 (10)	0.0596 (4)
H10	0.8301	−0.1729	0.5622	0.071*
C11	0.86323 (4)	−0.0313 (3)	0.51858 (9)	0.0495 (3)
C12	0.88775 (4)	0.3132 (3)	0.39218 (8)	0.0436 (3)
H12	0.8869	0.4750	0.4088	0.052*
C13	0.90741 (3)	0.3082 (2)	0.33675 (7)	0.0416 (3)
C14	0.92695 (4)	0.4952 (3)	0.33202 (10)	0.0569 (4)
H14	0.9284	0.6236	0.3641	0.068*
C15	0.94436 (5)	0.4954 (3)	0.28052 (12)	0.0671 (5)
H15	0.9573	0.6232	0.2783	0.080*
C16	0.94255 (4)	0.3079 (3)	0.23278 (11)	0.0645 (5)
H16	0.9543	0.3078	0.1982	0.077*
C17	0.92334 (5)	0.1211 (3)	0.23624 (10)	0.0638 (4)
H17	0.9219	−0.0060	0.2036	0.077*
C18	0.90601 (4)	0.1203 (3)	0.28822 (9)	0.0537 (4)
H18	0.8932	−0.0088	0.2905	0.064*
C19	0.85253 (3)	0.2291 (3)	0.35328 (9)	0.0491 (3)
H19A	0.8532	0.0695	0.3360	0.059*
H19B	0.8413	0.2278	0.3915	0.059*
C20	0.83275 (4)	0.3740 (3)	0.28526 (8)	0.0457 (3)
C21	0.80262 (3)	0.2639 (3)	0.22939 (8)	0.0436 (3)
C22	0.79031 (4)	0.0502 (3)	0.24330 (10)	0.0511 (4)
H22	0.8010	−0.0303	0.2888	0.061*
C23	0.76239 (4)	−0.0443 (3)	0.19061 (10)	0.0570 (4)
H23	0.7542	−0.1870	0.2005	0.068*
C24	0.74683 (4)	0.0746 (3)	0.12351 (10)	0.0596 (4)
C25	0.75831 (5)	0.2881 (3)	0.10805 (10)	0.0640 (4)
H25	0.7474	0.3677	0.0625	0.077*
C26	0.78613 (4)	0.3814 (3)	0.16101 (9)	0.0542 (4)
H26	0.7940	0.5249	0.1510	0.065*
O1	0.94554 (4)	0.4569 (2)	0.51323 (8)	0.0786 (4)
O2	0.84006 (3)	0.5733 (2)	0.27563 (7)	0.0614 (3)
F1	0.86105 (3)	−0.20686 (17)	0.46719 (6)	0.0687 (3)
Cl1	0.712537 (14)	−0.05059 (13)	0.05552 (4)	0.0982 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0636 (11)	0.1197 (18)	0.0452 (9)	−0.0021 (11)	0.0071 (8)	−0.0002 (10)
C2	0.0520 (10)	0.131 (2)	0.0690 (12)	0.0048 (11)	0.0131 (9)	−0.0203 (13)
C3	0.0525 (9)	0.0754 (12)	0.0553 (9)	−0.0003 (8)	0.0063 (8)	−0.0035 (9)
C4	0.0535 (8)	0.0638 (10)	0.0385 (7)	−0.0064 (7)	0.0153 (6)	−0.0048 (7)
C5	0.0491 (7)	0.0456 (7)	0.0346 (6)	−0.0001 (6)	0.0137 (6)	−0.0022 (5)
C6	0.0514 (8)	0.0468 (7)	0.0332 (6)	0.0044 (6)	0.0139 (6)	0.0040 (5)
C7	0.0671 (9)	0.0514 (8)	0.0399 (7)	0.0029 (7)	0.0177 (7)	−0.0003 (6)
C8	0.0798 (11)	0.0640 (10)	0.0449 (8)	0.0165 (9)	0.0266 (8)	0.0009 (7)
C9	0.0740 (11)	0.0741 (11)	0.0540 (9)	0.0199 (9)	0.0361 (9)	0.0158 (8)
C10	0.0645 (10)	0.0596 (10)	0.0608 (10)	0.0028 (8)	0.0290 (8)	0.0130 (8)
C11	0.0602 (9)	0.0465 (8)	0.0435 (8)	0.0038 (7)	0.0191 (7)	0.0019 (6)
C12	0.0498 (7)	0.0440 (7)	0.0381 (7)	0.0003 (6)	0.0158 (6)	0.0002 (6)
C13	0.0437 (7)	0.0447 (7)	0.0350 (6)	−0.0019 (6)	0.0111 (5)	0.0005 (5)
C14	0.0669 (10)	0.0517 (9)	0.0554 (9)	−0.0145 (8)	0.0247 (8)	−0.0084 (7)
C15	0.0688 (11)	0.0698 (11)	0.0700 (11)	−0.0222 (9)	0.0328 (9)	−0.0019 (9)
C16	0.0640 (10)	0.0797 (12)	0.0605 (10)	−0.0017 (9)	0.0350 (9)	0.0027 (9)
C17	0.0783 (11)	0.0650 (10)	0.0564 (9)	−0.0045 (9)	0.0334 (9)	−0.0131 (8)
C18	0.0648 (9)	0.0505 (8)	0.0509 (8)	−0.0118 (7)	0.0260 (7)	−0.0076 (7)
C19	0.0458 (7)	0.0585 (9)	0.0445 (8)	0.0021 (7)	0.0169 (6)	0.0104 (6)
C20	0.0487 (7)	0.0494 (8)	0.0434 (7)	0.0060 (6)	0.0210 (6)	0.0053 (6)
C21	0.0444 (7)	0.0474 (7)	0.0428 (7)	0.0075 (6)	0.0195 (6)	0.0044 (6)
C22	0.0483 (8)	0.0550 (9)	0.0530 (8)	0.0065 (7)	0.0208 (7)	0.0114 (7)
C23	0.0503 (8)	0.0549 (9)	0.0700 (10)	−0.0021 (7)	0.0253 (8)	0.0060 (8)
C24	0.0470 (8)	0.0689 (11)	0.0603 (10)	−0.0037 (8)	0.0140 (7)	−0.0006 (8)
C25	0.0627 (10)	0.0692 (11)	0.0525 (9)	0.0006 (9)	0.0085 (8)	0.0134 (8)
C26	0.0588 (9)	0.0514 (8)	0.0508 (8)	0.0003 (7)	0.0157 (7)	0.0090 (7)
O1	0.0813 (9)	0.0664 (8)	0.0730 (9)	−0.0223 (7)	0.0049 (7)	−0.0020 (6)
O2	0.0690 (7)	0.0502 (6)	0.0584 (7)	−0.0017 (5)	0.0118 (6)	0.0076 (5)
F1	0.0890 (7)	0.0537 (6)	0.0725 (7)	−0.0151 (5)	0.0387 (6)	−0.0136 (5)
Cl1	0.0709 (3)	0.1139 (5)	0.0894 (4)	−0.0320 (3)	−0.0017 (3)	0.0073 (3)

Geometric parameters (Å, º) top

C1—C2	1.461 (3)	C13—C14	1.382 (2)
C1—C3	1.512 (3)	C13—C18	1.383 (2)
C1—H1A	0.9700	C14—C15	1.382 (2)
C1—H1B	0.9700	C14—H14	0.9300
C2—C3	1.514 (3)	C15—C16	1.369 (3)
C2—H2A	0.9700	C15—H15	0.9300
C2—H2B	0.9700	C16—C17	1.366 (3)
C3—C4	1.467 (3)	C16—H16	0.9300
C3—H3	0.9800	C17—C18	1.387 (2)
C4—O1	1.216 (2)	C17—H17	0.9300
C4—C5	1.525 (2)	C18—H18	0.9300
C5—C6	1.5266 (19)	C19—C20	1.506 (2)
C5—C12	1.551 (2)	C19—H19A	0.9700
C5—H5	0.9800	C19—H19B	0.9700
C6—C11	1.381 (2)	C20—O2	1.2117 (19)
C6—C7	1.394 (2)	C20—C21	1.502 (2)
C7—C8	1.388 (2)	C21—C22	1.389 (2)
C7—H7	0.9300	C21—C26	1.392 (2)
C8—C9	1.375 (3)	C22—C23	1.381 (2)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.380 (3)	C23—C24	1.371 (3)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.377 (2)	C24—C25	1.382 (3)
C10—H10	0.9300	C24—Cl1	1.7425 (18)
C11—F1	1.3583 (18)	C25—C26	1.378 (2)
C12—C13	1.5182 (19)	C25—H25	0.9300
C12—C19	1.527 (2)	C26—H26	0.9300
C12—H12	0.9800

C2—C1—C3	61.19 (13)	C13—C12—H12	108.1
C2—C1—H1A	117.6	C19—C12—H12	108.1
C3—C1—H1A	117.6	C5—C12—H12	108.1
C2—C1—H1B	117.6	C14—C13—C18	117.53 (13)
C3—C1—H1B	117.6	C14—C13—C12	120.74 (13)
H1A—C1—H1B	114.8	C18—C13—C12	121.72 (13)
C1—C2—C3	61.07 (13)	C13—C14—C15	121.34 (15)
C1—C2—H2A	117.7	C13—C14—H14	119.3
C3—C2—H2A	117.7	C15—C14—H14	119.3
C1—C2—H2B	117.7	C16—C15—C14	120.23 (16)
C3—C2—H2B	117.7	C16—C15—H15	119.9
H2A—C2—H2B	114.8	C14—C15—H15	119.9
C4—C3—C1	116.42 (17)	C17—C16—C15	119.53 (15)
C4—C3—C2	117.72 (19)	C17—C16—H16	120.2
C1—C3—C2	57.75 (13)	C15—C16—H16	120.2
C4—C3—H3	117.2	C16—C17—C18	120.28 (16)
C1—C3—H3	117.2	C16—C17—H17	119.9
C2—C3—H3	117.2	C18—C17—H17	119.9
O1—C4—C3	122.04 (16)	C13—C18—C17	121.08 (15)
O1—C4—C5	121.34 (15)	C13—C18—H18	119.5
C3—C4—C5	116.51 (15)	C17—C18—H18	119.5
C4—C5—C6	107.17 (11)	C20—C19—C12	114.70 (12)
C4—C5—C12	112.84 (12)	C20—C19—H19A	108.6
C6—C5—C12	112.52 (12)	C12—C19—H19A	108.6
C4—C5—H5	108.0	C20—C19—H19B	108.6
C6—C5—H5	108.0	C12—C19—H19B	108.6
C12—C5—H5	108.0	H19A—C19—H19B	107.6
C11—C6—C7	116.25 (13)	O2—C20—C21	120.28 (13)
C11—C6—C5	121.61 (13)	O2—C20—C19	122.37 (14)
C7—C6—C5	122.11 (13)	C21—C20—C19	117.33 (13)
C8—C7—C6	121.30 (16)	C22—C21—C26	118.49 (14)
C8—C7—H7	119.3	C22—C21—C20	122.78 (13)
C6—C7—H7	119.3	C26—C21—C20	118.73 (13)
C9—C8—C7	120.02 (16)	C23—C22—C21	120.96 (15)
C9—C8—H8	120.0	C23—C22—H22	119.5
C7—C8—H8	120.0	C21—C22—H22	119.5
C8—C9—C10	120.37 (15)	C24—C23—C22	119.22 (16)
C8—C9—H9	119.8	C24—C23—H23	120.4
C10—C9—H9	119.8	C22—C23—H23	120.4
C11—C10—C9	118.19 (16)	C23—C24—C25	121.31 (16)
C11—C10—H10	120.9	C23—C24—Cl1	119.07 (14)
C9—C10—H10	120.9	C25—C24—Cl1	119.60 (14)
F1—C11—C10	117.77 (15)	C26—C25—C24	119.07 (16)
F1—C11—C6	118.35 (13)	C26—C25—H25	120.5
C10—C11—C6	123.86 (15)	C24—C25—H25	120.5
C13—C12—C19	111.63 (11)	C25—C26—C21	120.95 (15)
C13—C12—C5	111.38 (12)	C25—C26—H26	119.5
C19—C12—C5	109.43 (12)	C21—C26—H26	119.5

C2—C1—C3—C4	−107.5 (2)	C5—C12—C13—C14	−102.94 (16)
C1—C2—C3—C4	105.2 (2)	C19—C12—C13—C18	−44.28 (19)
C1—C3—C4—O1	38.4 (2)	C5—C12—C13—C18	78.37 (17)
C2—C3—C4—O1	−27.3 (3)	C18—C13—C14—C15	0.3 (3)
C1—C3—C4—C5	−137.90 (16)	C12—C13—C14—C15	−178.45 (16)
C2—C3—C4—C5	156.43 (15)	C13—C14—C15—C16	−0.1 (3)
O1—C4—C5—C6	−94.60 (18)	C14—C15—C16—C17	0.2 (3)
C3—C4—C5—C6	81.72 (16)	C15—C16—C17—C18	−0.6 (3)
O1—C4—C5—C12	29.8 (2)	C14—C13—C18—C17	−0.7 (3)
C3—C4—C5—C12	−153.86 (13)	C12—C13—C18—C17	178.06 (15)
C4—C5—C6—C11	−138.34 (15)	C16—C17—C18—C13	0.8 (3)
C12—C5—C6—C11	97.05 (16)	C13—C12—C19—C20	−61.19 (17)
C4—C5—C6—C7	43.57 (18)	C5—C12—C19—C20	175.04 (12)
C12—C5—C6—C7	−81.04 (17)	C12—C19—C20—O2	−20.5 (2)
C11—C6—C7—C8	0.7 (2)	C12—C19—C20—C21	160.82 (12)
C5—C6—C7—C8	178.87 (14)	O2—C20—C21—C22	−170.23 (14)
C6—C7—C8—C9	−0.5 (3)	C19—C20—C21—C22	8.5 (2)
C7—C8—C9—C10	−0.1 (3)	O2—C20—C21—C26	9.2 (2)
C8—C9—C10—C11	0.6 (3)	C19—C20—C21—C26	−172.05 (13)
C9—C10—C11—F1	−178.87 (15)	C26—C21—C22—C23	0.1 (2)
C9—C10—C11—C6	−0.5 (3)	C20—C21—C22—C23	179.58 (14)
C7—C6—C11—F1	178.22 (13)	C21—C22—C23—C24	0.4 (2)
C5—C6—C11—F1	0.0 (2)	C22—C23—C24—C25	−0.7 (3)
C7—C6—C11—C10	−0.2 (2)	C22—C23—C24—Cl1	177.56 (13)
C5—C6—C11—C10	−178.39 (15)	C23—C24—C25—C26	0.6 (3)
C4—C5—C12—C13	61.90 (15)	Cl1—C24—C25—C26	−177.70 (14)
C6—C5—C12—C13	−176.68 (12)	C24—C25—C26—C21	−0.1 (3)
C4—C5—C12—C19	−174.20 (12)	C22—C21—C26—C25	−0.3 (2)
C6—C5—C12—C19	−52.77 (16)	C20—C21—C26—C25	−179.75 (15)
C19—C12—C13—C14	134.40 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···F1ⁱ	0.98	2.54	3.433 (2)	151

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₂ClFO₂
M_r	420.89
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	43.0465 (15), 5.7257 (2), 18.2828 (6)
β (°)	109.103 (2)
V (Å³)	4258.0 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.940, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	20606, 5308, 3857
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.146, 1.02
No. of reflections	5308
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.41

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), 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
C12—H12···F1ⁱ	0.98	2.54	3.433 (2)	151

Symmetry code: (i) x, y+1, z.

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS also thanks the DST for an Inspire fellowship.

References

Bennett, I., Broom, N. J. P., Cassels, R., Elder, J. S., Masson, N. D. & O'Hanlon, P. J. (1999). Bioorg. Med. Chem. Lett. 9, 1847–1852. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Li, K.-Z., Chen, Y.-T., Zhao, C.-W., Wei, G.-D. & He, Q.-P. (2008). Acta Cryst. E64, o1665. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sato, K., Yamazoe, S., Yamamoto, R., Ohata, S., Tarui, A., Omote, M., Kumadaki, I. & Ando, A. (2008). Org. Lett. 10, 2405–2408. Web of Science CrossRef PubMed CAS 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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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

5-(4-Chloro­phen­yl)-1-cyclo­propyl-2-(2-fluoro­phen­yl)-3-phenyl­pentane-1,5-dione

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