5-(4-Chloro-phen-yl)-1-cyclo-propyl-2-(2-fluoro-phen-yl)-3-phenyl-pentane-1,5-dione.

In the title compound, C(26)H(22)ClFO(2), the cyclo-propane 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, mol-ecules 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 = 420.89

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.146

S = 1.02

5308 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.41 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813001074/su2549sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001074/su2549Isup3.cml

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

C26H22ClFO2	F(000) = 1760
Mr = 420.89	Dx = 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

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

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(Fo2) + (0.0784P)2 + 1.3969P] where P = (Fo2 + 2Fc2)/3
5308 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .