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

In the title compound, C(26)H(22)F(2)O(2), the cyclo-propane ring makes dihedral angles of 47.6 (2), 51.3 (2) and 63.9 (2)° with the 2-fluoro-substituted phenyl ring, the unsubstituted phenyl ring and the 4-fluoro-substituted phenyl ring, respectively. There is a short C-H⋯F contact in the molecule. In the crystal, weak C-H⋯F hydrogen bonds lead to chains of mol-ecules extending along the b-axis direction.

Related literature

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

Experimental

Crystal data

C26H22F2O2

M = 404.44

Monoclinic,

a = 38.9453 (14) Å

b = 5.7769 (2) Å

c = 18.3045 (7) Å

β = 95.334 (2)°

V = 4100.4 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 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 = 0.972, T max = 0.982

18721 measured reflections

5017 independent reflections

3326 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.133

S = 1.02

5017 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.20 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 (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/S1600536813000032/pv2615sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000032/pv2615Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000032/pv2615Isup3.cml

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

C26H22F2O2	F(000) = 1696
Mr = 404.44	Dx = 1.310 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5017 reflections
a = 38.9453 (14) Å	θ = 1.1–28.3°
b = 5.7769 (2) Å	µ = 0.09 mm−1
c = 18.3045 (7) Å	T = 293 K
β = 95.334 (2)°	Block, colourless
V = 4100.4 (3) Å3	0.30 × 0.25 × 0.20 mm
Z = 8

Bruker SMART APEXII area-detector diffractometer	5017 independent reflections
Radiation source: fine-focus sealed tube	3326 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω and φ scans	θmax = 28.3°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −50→43
Tmin = 0.972, Tmax = 0.982	k = −7→7
18721 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0504P)2 + 2.5291P] where P = (Fo2 + 2Fc2)/3
5017 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.20 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	0.00262 (5)	0.6122 (5)	0.08432 (12)	0.0835 (7)
H1A	−0.0048	0.7524	0.0583	0.100*
H1B	−0.0123	0.4795	0.0741	0.100*
C2	0.01946 (5)	0.6368 (5)	0.15898 (11)	0.0768 (6)
H2A	0.0149	0.5191	0.1946	0.092*
H2B	0.0224	0.7920	0.1788	0.092*
C3	0.04098 (5)	0.5684 (4)	0.09772 (11)	0.0628 (5)
H3	0.0487	0.4070	0.0966	0.075*
C4	0.06452 (4)	0.7452 (3)	0.07330 (9)	0.0494 (4)
C5	0.10063 (4)	0.6636 (3)	0.05999 (8)	0.0402 (3)
H5	0.0987	0.5069	0.0395	0.048*
C6	0.12138 (4)	0.6493 (3)	0.13465 (8)	0.0403 (3)
C7	0.12022 (4)	0.8227 (3)	0.18717 (8)	0.0473 (4)
H7	0.1065	0.9523	0.1765	0.057*
C8	0.13904 (5)	0.8064 (3)	0.25495 (9)	0.0553 (4)
H8	0.1378	0.9238	0.2894	0.066*
C9	0.15958 (5)	0.6159 (3)	0.27130 (9)	0.0565 (5)
H9	0.1721	0.6045	0.3170	0.068*
C10	0.16176 (5)	0.4425 (3)	0.22048 (10)	0.0549 (4)
H10	0.1758	0.3142	0.2310	0.066*
C11	0.14271 (4)	0.4636 (3)	0.15372 (9)	0.0464 (4)
C12	0.11779 (4)	0.8197 (3)	0.00456 (8)	0.0406 (3)
H12	0.1183	0.9786	0.0233	0.049*
C13	0.09715 (4)	0.8184 (3)	−0.07003 (8)	0.0397 (3)
C14	0.07706 (5)	1.0070 (3)	−0.09310 (10)	0.0536 (4)
H14	0.0760	1.1340	−0.0622	0.064*
C15	0.05858 (5)	1.0098 (4)	−0.16130 (11)	0.0645 (5)
H15	0.0451	1.1378	−0.1757	0.077*
C16	0.05997 (5)	0.8243 (4)	−0.20788 (10)	0.0615 (5)
H16	0.0476	0.8265	−0.2539	0.074*
C17	0.07965 (5)	0.6367 (3)	−0.18606 (10)	0.0596 (5)
H17	0.0807	0.5106	−0.2174	0.072*
C18	0.09808 (5)	0.6331 (3)	−0.11760 (9)	0.0506 (4)
H18	0.1113	0.5039	−0.1034	0.061*
C19	0.15504 (4)	0.7407 (3)	−0.00056 (9)	0.0468 (4)
H19A	0.1669	0.7392	0.0484	0.056*
H19B	0.1548	0.5833	−0.0190	0.056*
C20	0.17512 (4)	0.8902 (3)	−0.04919 (8)	0.0436 (4)
C21	0.20585 (4)	0.7867 (3)	−0.08010 (8)	0.0417 (3)
C22	0.22127 (5)	0.9066 (3)	−0.13411 (10)	0.0552 (4)
H22	0.2121	1.0477	−0.1507	0.066*
C23	0.24992 (5)	0.8207 (4)	−0.16359 (11)	0.0689 (6)
H23	0.2600	0.9015	−0.2000	0.083*
C24	0.26322 (5)	0.6147 (4)	−0.13818 (11)	0.0625 (5)
C25	0.24916 (5)	0.4901 (3)	−0.08487 (11)	0.0613 (5)
H25	0.2589	0.3506	−0.0682	0.074*
C26	0.22017 (4)	0.5761 (3)	−0.05628 (10)	0.0520 (4)
H26	0.2101	0.4921	−0.0206	0.062*
O1	0.05644 (4)	0.9477 (3)	0.06815 (9)	0.0757 (4)
O2	0.16725 (3)	1.0902 (2)	−0.06242 (7)	0.0608 (3)
F1	0.14564 (3)	0.29321 (18)	0.10349 (6)	0.0686 (3)
F2	0.29148 (3)	0.5295 (3)	−0.16639 (8)	0.0974 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0478 (11)	0.132 (2)	0.0718 (13)	−0.0092 (12)	0.0112 (10)	−0.0214 (14)
C2	0.0593 (12)	0.1175 (19)	0.0566 (11)	0.0007 (12)	0.0211 (10)	0.0027 (12)
C3	0.0491 (10)	0.0742 (13)	0.0678 (12)	−0.0008 (9)	0.0193 (9)	−0.0031 (10)
C4	0.0478 (9)	0.0616 (11)	0.0393 (8)	0.0067 (8)	0.0073 (7)	−0.0017 (8)
C5	0.0431 (8)	0.0415 (8)	0.0367 (7)	0.0007 (7)	0.0072 (6)	−0.0015 (6)
C6	0.0438 (8)	0.0432 (8)	0.0350 (7)	−0.0025 (7)	0.0096 (6)	0.0018 (6)
C7	0.0551 (10)	0.0476 (9)	0.0403 (8)	0.0012 (8)	0.0107 (7)	−0.0014 (7)
C8	0.0668 (11)	0.0597 (11)	0.0402 (8)	−0.0128 (9)	0.0092 (8)	−0.0061 (8)
C9	0.0608 (11)	0.0682 (12)	0.0395 (8)	−0.0144 (9)	−0.0011 (8)	0.0081 (8)
C10	0.0562 (10)	0.0533 (10)	0.0542 (10)	0.0009 (8)	0.0002 (8)	0.0125 (8)
C11	0.0545 (10)	0.0425 (9)	0.0428 (8)	−0.0013 (7)	0.0073 (7)	−0.0007 (7)
C12	0.0445 (8)	0.0402 (8)	0.0377 (7)	−0.0009 (7)	0.0071 (6)	0.0000 (6)
C13	0.0393 (8)	0.0422 (8)	0.0383 (7)	0.0015 (6)	0.0080 (6)	0.0014 (6)
C14	0.0599 (11)	0.0474 (9)	0.0532 (10)	0.0121 (8)	0.0037 (8)	−0.0021 (8)
C15	0.0638 (12)	0.0655 (12)	0.0625 (11)	0.0212 (10)	−0.0038 (10)	0.0098 (10)
C16	0.0576 (11)	0.0767 (13)	0.0478 (9)	0.0017 (10)	−0.0072 (8)	0.0041 (9)
C17	0.0727 (12)	0.0582 (11)	0.0468 (9)	0.0041 (9)	−0.0006 (9)	−0.0088 (8)
C18	0.0595 (10)	0.0470 (9)	0.0450 (9)	0.0119 (8)	0.0027 (8)	−0.0011 (7)
C19	0.0426 (8)	0.0560 (10)	0.0420 (8)	−0.0002 (7)	0.0046 (7)	0.0090 (7)
C20	0.0448 (9)	0.0466 (9)	0.0389 (8)	−0.0052 (7)	0.0013 (7)	0.0029 (7)
C21	0.0393 (8)	0.0467 (9)	0.0386 (7)	−0.0071 (7)	0.0009 (6)	−0.0019 (7)
C22	0.0538 (10)	0.0564 (10)	0.0564 (10)	−0.0007 (8)	0.0111 (8)	0.0107 (8)
C23	0.0596 (12)	0.0859 (15)	0.0649 (12)	−0.0009 (11)	0.0246 (10)	0.0106 (11)
C24	0.0458 (10)	0.0771 (13)	0.0657 (12)	0.0027 (9)	0.0114 (9)	−0.0142 (10)
C25	0.0554 (11)	0.0542 (10)	0.0735 (12)	0.0065 (9)	0.0021 (10)	−0.0025 (10)
C26	0.0503 (10)	0.0512 (10)	0.0548 (10)	−0.0027 (8)	0.0061 (8)	0.0052 (8)
O1	0.0719 (9)	0.0683 (9)	0.0911 (11)	0.0222 (7)	0.0290 (8)	0.0081 (8)
O2	0.0657 (8)	0.0478 (7)	0.0717 (8)	0.0030 (6)	0.0217 (7)	0.0074 (6)
F1	0.0890 (8)	0.0519 (6)	0.0636 (6)	0.0169 (6)	0.0003 (6)	−0.0103 (5)
F2	0.0719 (8)	0.1137 (11)	0.1122 (11)	0.0203 (7)	0.0387 (8)	−0.0110 (9)

C1—C2	1.467 (3)	C13—C18	1.382 (2)
C1—C3	1.513 (3)	C13—C14	1.384 (2)
C1—H1A	0.9700	C14—C15	1.382 (3)
C1—H1B	0.9700	C14—H14	0.9300
C2—C3	1.514 (3)	C15—C16	1.373 (3)
C2—H2A	0.9700	C15—H15	0.9300
C2—H2B	0.9700	C16—C17	1.366 (3)
C3—C4	1.469 (3)	C16—H16	0.9300
C3—H3	0.9800	C17—C18	1.385 (2)
C4—O1	1.213 (2)	C17—H17	0.9300
C4—C5	1.524 (2)	C18—H18	0.9300
C5—C6	1.524 (2)	C19—C20	1.510 (2)
C5—C12	1.554 (2)	C19—H19A	0.9700
C5—H5	0.9800	C19—H19B	0.9700
C6—C11	1.382 (2)	C20—O2	1.2138 (19)
C6—C7	1.392 (2)	C20—C21	1.495 (2)
C7—C8	1.384 (2)	C21—C22	1.389 (2)
C7—H7	0.9300	C21—C26	1.391 (2)
C8—C9	1.377 (3)	C22—C23	1.376 (3)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.375 (3)	C23—C24	1.362 (3)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.375 (2)	C24—F2	1.351 (2)
C10—H10	0.9300	C24—C25	1.367 (3)
C11—F1	1.3589 (18)	C25—C26	1.380 (3)
C12—C13	1.519 (2)	C25—H25	0.9300
C12—C19	1.532 (2)	C26—H26	0.9300
C12—H12	0.9800
C2—C1—C3	61.04 (13)	C13—C12—H12	108.1
C2—C1—H1A	117.7	C19—C12—H12	108.1
C3—C1—H1A	117.7	C5—C12—H12	108.1
C2—C1—H1B	117.7	C18—C13—C14	117.68 (15)
C3—C1—H1B	117.7	C18—C13—C12	121.82 (14)
H1A—C1—H1B	114.8	C14—C13—C12	120.49 (14)
C1—C2—C3	60.98 (13)	C15—C14—C13	121.11 (16)
C1—C2—H2A	117.7	C15—C14—H14	119.4
C3—C2—H2A	117.7	C13—C14—H14	119.4
C1—C2—H2B	117.7	C16—C15—C14	120.31 (17)
C3—C2—H2B	117.7	C16—C15—H15	119.8
H2A—C2—H2B	114.8	C14—C15—H15	119.8
C4—C3—C1	117.96 (19)	C17—C16—C15	119.41 (17)
C4—C3—C2	116.61 (18)	C17—C16—H16	120.3
C1—C3—C2	57.98 (13)	C15—C16—H16	120.3
C4—C3—H3	117.1	C16—C17—C18	120.40 (17)
C1—C3—H3	117.1	C16—C17—H17	119.8
C2—C3—H3	117.1	C18—C17—H17	119.8
O1—C4—C3	121.98 (17)	C13—C18—C17	121.09 (16)
O1—C4—C5	121.47 (16)	C13—C18—H18	119.5
C3—C4—C5	116.41 (15)	C17—C18—H18	119.5
C6—C5—C4	107.08 (12)	C20—C19—C12	114.29 (13)
C6—C5—C12	113.11 (12)	C20—C19—H19A	108.7
C4—C5—C12	112.61 (13)	C12—C19—H19A	108.7
C6—C5—H5	107.9	C20—C19—H19B	108.7
C4—C5—H5	107.9	C12—C19—H19B	108.7
C12—C5—H5	107.9	H19A—C19—H19B	107.6
C11—C6—C7	116.21 (14)	O2—C20—C21	120.10 (14)
C11—C6—C5	121.66 (13)	O2—C20—C19	121.79 (15)
C7—C6—C5	122.13 (14)	C21—C20—C19	118.10 (14)
C8—C7—C6	121.43 (16)	C22—C21—C26	118.17 (16)
C8—C7—H7	119.3	C22—C21—C20	118.95 (15)
C6—C7—H7	119.3	C26—C21—C20	122.88 (14)
C9—C8—C7	119.85 (16)	C23—C22—C21	121.29 (17)
C9—C8—H8	120.1	C23—C22—H22	119.4
C7—C8—H8	120.1	C21—C22—H22	119.4
C10—C9—C8	120.41 (16)	C24—C23—C22	118.51 (18)
C10—C9—H9	119.8	C24—C23—H23	120.7
C8—C9—H9	119.8	C22—C23—H23	120.7
C11—C10—C9	118.35 (17)	F2—C24—C23	119.03 (19)
C11—C10—H10	120.8	F2—C24—C25	118.37 (19)
C9—C10—H10	120.8	C23—C24—C25	122.60 (18)
F1—C11—C10	117.72 (15)	C24—C25—C26	118.49 (18)
F1—C11—C6	118.55 (14)	C24—C25—H25	120.8
C10—C11—C6	123.72 (15)	C26—C25—H25	120.8
C13—C12—C19	111.64 (12)	C25—C26—C21	120.94 (17)
C13—C12—C5	111.11 (12)	C25—C26—H26	119.5
C19—C12—C5	109.56 (12)	C21—C26—H26	119.5
C2—C1—C3—C4	−105.4 (2)	C5—C12—C13—C18	−76.16 (18)
C1—C2—C3—C4	107.8 (2)	C19—C12—C13—C14	−132.39 (16)
C1—C3—C4—O1	27.0 (3)	C5—C12—C13—C14	104.98 (17)
C2—C3—C4—O1	−39.1 (3)	C18—C13—C14—C15	0.0 (3)
C1—C3—C4—C5	−157.23 (16)	C12—C13—C14—C15	178.94 (16)
C2—C3—C4—C5	136.69 (17)	C13—C14—C15—C16	−0.3 (3)
O1—C4—C5—C6	95.68 (19)	C14—C15—C16—C17	0.3 (3)
C3—C4—C5—C6	−80.10 (17)	C15—C16—C17—C18	0.0 (3)
O1—C4—C5—C12	−29.3 (2)	C14—C13—C18—C17	0.3 (3)
C3—C4—C5—C12	154.95 (14)	C12—C13—C18—C17	−178.64 (16)
C4—C5—C6—C11	136.23 (16)	C16—C17—C18—C13	−0.3 (3)
C12—C5—C6—C11	−99.12 (17)	C13—C12—C19—C20	60.36 (18)
C4—C5—C6—C7	−44.37 (19)	C5—C12—C19—C20	−176.12 (13)
C12—C5—C6—C7	80.28 (17)	C12—C19—C20—O2	23.4 (2)
C11—C6—C7—C8	−1.0 (2)	C12—C19—C20—C21	−157.76 (14)
C5—C6—C7—C8	179.55 (15)	O2—C20—C21—C22	−11.6 (2)
C6—C7—C8—C9	0.3 (3)	C19—C20—C21—C22	169.58 (15)
C7—C8—C9—C10	0.6 (3)	O2—C20—C21—C26	167.32 (16)
C8—C9—C10—C11	−0.6 (3)	C19—C20—C21—C26	−11.5 (2)
C9—C10—C11—F1	178.71 (15)	C26—C21—C22—C23	0.0 (3)
C9—C10—C11—C6	−0.1 (3)	C20—C21—C22—C23	179.00 (17)
C7—C6—C11—F1	−177.89 (14)	C21—C22—C23—C24	−0.5 (3)
C5—C6—C11—F1	1.5 (2)	C22—C23—C24—F2	−179.57 (18)
C7—C6—C11—C10	0.9 (2)	C22—C23—C24—C25	0.2 (3)
C5—C6—C11—C10	−179.62 (15)	F2—C24—C25—C26	−179.61 (17)
C6—C5—C12—C13	177.05 (12)	C23—C24—C25—C26	0.6 (3)
C4—C5—C12—C13	−61.37 (16)	C24—C25—C26—C21	−1.1 (3)
C6—C5—C12—C19	53.22 (17)	C22—C21—C26—C25	0.8 (2)
C4—C5—C12—C19	174.80 (13)	C20—C21—C26—C25	−178.12 (16)
C19—C12—C13—C18	46.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···F1i	0.98	2.51	3.402 (2)	151
C5—H5···F1	0.98	2.42	2.833 (2)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯F1i	0.98	2.51	3.402 (2)	151
C5—H5⋯F1	0.98	2.42	2.833 (2)	105

Symmetry code: (i) .