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

In the title compound, C26H22ClFO2, the cyclo-propane ring is disordered over two orientations, with site-occupancy factors of 0.64 (2) and 0.36 (2). The major occupancy component of the cyclo-propane ring makes dihedral angles of 47.6 (7), 50.4 (7) and 65.4 (7)° with the fluoro-, chloro- and unsubstituted benzene rings, respectively [the corresponding values for the minor occupancy component are 47.6 (12), 51.0 (12) and 60.9 (12)°]. An intra-molecular C-H⋯O hydrogen bond occurs. The F and Cl atoms deviate by 0.0508 (12) and 0.0592 (7) Å from the planes of their attached benzene rings. In the crystal, C-H⋯F hydrogen bonds link the mol-ecules into chains 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 a related structure, see: Li et al. (2008 ▶).

Experimental

Crystal data

C26H22ClFO2

M = 420.89

Monoclinic,

a = 40.0712 (18) Å

b = 5.6840 (2) Å

c = 18.6470 (8) Å

β = 92.903 (2)°

V = 4241.7 (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 = 0.959

20059 measured reflections

5298 independent reflections

3397 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.125

S = 1.02

5298 reflections

299 parameters

40 restraints

H-atom parameters constrained

Δρmax = 0.30 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/S1600536813011276/pv2628sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011276/pv2628Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011276/pv2628Isup3.cml

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

C26H22ClFO2	F(000) = 1760
Mr = 420.89	Dx = 1.318 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5298 reflections
a = 40.0712 (18) Å	θ = 2.0–28.4°
b = 5.6840 (2) Å	µ = 0.21 mm−1
c = 18.6470 (8) Å	T = 293 K
β = 92.903 (2)°	Block, colourless
V = 4241.7 (3) Å3	0.30 × 0.25 × 0.20 mm
Z = 8

Bruker SMART APEXII area-detector diffractometer	5298 independent reflections
Radiation source: fine-focus sealed tube	3397 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω and φ scans	θmax = 28.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −53→46
Tmin = 0.940, Tmax = 0.959	k = −6→7
20059 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0482P)2 + 2.4951P] where P = (Fo2 + 2Fc2)/3
5298 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.30 e Å−3
40 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	Occ. (<1)
C1	0.4715 (2)	0.5122 (16)	0.0640 (6)	0.096 (2)	0.64 (2)
H1A	0.4709	0.3917	0.0272	0.115*	0.64 (2)
H1B	0.4770	0.6687	0.0476	0.115*	0.64 (2)
C2	0.48333 (18)	0.4440 (17)	0.1374 (7)	0.087 (2)	0.64 (2)
H2A	0.4962	0.5588	0.1656	0.104*	0.64 (2)
H2B	0.4901	0.2820	0.1452	0.104*	0.64 (2)
C3	0.44683 (13)	0.4917 (11)	0.1227 (6)	0.061 (2)	0.64 (2)
H3	0.4378	0.6380	0.1417	0.074*	0.64 (2)
C1'	0.4818 (4)	0.455 (3)	0.0871 (9)	0.095 (3)	0.36 (2)
H1'1	0.4849	0.3187	0.0568	0.114*	0.36 (2)
H1'2	0.4923	0.5981	0.0711	0.114*	0.36 (2)
C2'	0.4808 (4)	0.416 (3)	0.1652 (9)	0.082 (3)	0.36 (2)
H2'1	0.4908	0.5347	0.1968	0.098*	0.36 (2)
H2'2	0.4834	0.2555	0.1826	0.098*	0.36 (2)
C3'	0.4489 (3)	0.477 (2)	0.1234 (11)	0.076 (4)	0.36 (2)
H3'	0.4405	0.6375	0.1296	0.092*	0.36 (2)
C4	0.42390 (4)	0.2929 (3)	0.11268 (8)	0.0460 (4)
C5	0.38759 (4)	0.3590 (3)	0.09542 (8)	0.0401 (4)
H5	0.3872	0.5188	0.0757	0.048*
C6	0.36916 (4)	0.3639 (3)	0.16514 (8)	0.0402 (4)
C7	0.37293 (5)	0.1868 (3)	0.21654 (8)	0.0471 (4)
H7	0.3867	0.0594	0.2079	0.057*
C8	0.35657 (5)	0.1965 (4)	0.28028 (9)	0.0538 (5)
H8	0.3593	0.0755	0.3136	0.065*
C9	0.33630 (5)	0.3840 (4)	0.29427 (9)	0.0548 (5)
H9	0.3255	0.3907	0.3372	0.066*
C10	0.33198 (5)	0.5618 (3)	0.24466 (10)	0.0539 (5)
H10	0.3184	0.6900	0.2536	0.065*
C11	0.34822 (5)	0.5464 (3)	0.18149 (9)	0.0460 (4)
C12	0.37113 (4)	0.1936 (3)	0.03779 (8)	0.0412 (4)
H12	0.3693	0.0370	0.0592	0.049*
C13	0.39268 (4)	0.1719 (3)	−0.02688 (8)	0.0396 (4)
C14	0.39404 (5)	0.3478 (3)	−0.07800 (9)	0.0483 (4)
H14	0.3815	0.4839	−0.0730	0.058*
C15	0.41382 (5)	0.3247 (4)	−0.13672 (9)	0.0547 (5)
H15	0.4143	0.4434	−0.1710	0.066*
C16	0.43258 (5)	0.1254 (4)	−0.14354 (9)	0.0512 (4)
C17	0.43202 (5)	−0.0512 (4)	−0.09335 (10)	0.0568 (5)
H17	0.4450	−0.1854	−0.0981	0.068*
C18	0.41202 (5)	−0.0269 (3)	−0.03580 (10)	0.0524 (4)
H18	0.4115	−0.1472	−0.0021	0.063*
C19	0.33593 (4)	0.2781 (3)	0.01664 (9)	0.0471 (4)
H19A	0.3234	0.2913	0.0596	0.056*
H19B	0.3373	0.4340	−0.0042	0.056*
C20	0.31696 (4)	0.1198 (3)	−0.03613 (9)	0.0462 (4)
C21	0.28700 (4)	0.2161 (3)	−0.07669 (8)	0.0440 (4)
C22	0.27314 (5)	0.0884 (4)	−0.13424 (10)	0.0583 (5)
H22	0.2830	−0.0523	−0.1473	0.070*
C23	0.24508 (5)	0.1663 (5)	−0.17219 (12)	0.0718 (6)
H23	0.2364	0.0797	−0.2111	0.086*
C24	0.22983 (5)	0.3707 (4)	−0.15316 (12)	0.0690 (6)
H24	0.2104	0.4207	−0.1782	0.083*
C25	0.24318 (5)	0.5017 (4)	−0.09711 (12)	0.0663 (6)
H25	0.2330	0.6416	−0.0845	0.080*
C26	0.27181 (5)	0.4263 (4)	−0.05916 (11)	0.0567 (5)
H26	0.2809	0.5174	−0.0216	0.068*
O1	0.43244 (4)	0.0882 (2)	0.11642 (7)	0.0627 (4)
O2	0.32562 (4)	−0.0827 (2)	−0.04499 (8)	0.0632 (4)
F1	0.34265 (3)	0.72072 (19)	0.13225 (6)	0.0685 (3)
Cl1	0.456570 (16)	0.08923 (13)	−0.21778 (3)	0.0826 (2)

	U11	U22	U33	U12	U13	U23
C1	0.059 (3)	0.113 (4)	0.118 (4)	−0.011 (3)	0.019 (3)	0.030 (3)
C2	0.049 (3)	0.104 (4)	0.106 (5)	−0.015 (2)	−0.001 (4)	0.000 (5)
C3	0.044 (3)	0.055 (3)	0.084 (4)	−0.008 (3)	0.002 (3)	−0.013 (3)
C1'	0.069 (6)	0.128 (7)	0.091 (6)	−0.017 (5)	0.018 (5)	0.026 (6)
C2'	0.060 (5)	0.107 (6)	0.078 (6)	−0.021 (4)	0.000 (5)	0.006 (5)
C3'	0.062 (7)	0.094 (8)	0.074 (7)	−0.012 (6)	0.005 (6)	0.003 (6)
C4	0.0513 (10)	0.0538 (11)	0.0331 (7)	−0.0001 (9)	0.0035 (7)	−0.0024 (7)
C5	0.0479 (9)	0.0374 (8)	0.0352 (7)	−0.0046 (7)	0.0027 (6)	0.0009 (6)
C6	0.0447 (9)	0.0410 (9)	0.0345 (7)	−0.0061 (7)	−0.0004 (6)	−0.0028 (7)
C7	0.0522 (10)	0.0487 (10)	0.0404 (8)	0.0009 (8)	0.0019 (7)	0.0019 (7)
C8	0.0603 (11)	0.0629 (12)	0.0381 (8)	−0.0090 (10)	0.0010 (8)	0.0072 (8)
C9	0.0550 (11)	0.0699 (13)	0.0403 (9)	−0.0131 (10)	0.0094 (8)	−0.0109 (9)
C10	0.0535 (11)	0.0524 (11)	0.0566 (10)	−0.0019 (9)	0.0094 (8)	−0.0145 (9)
C11	0.0534 (10)	0.0403 (9)	0.0444 (8)	−0.0045 (8)	0.0015 (7)	−0.0017 (7)
C12	0.0506 (10)	0.0390 (8)	0.0343 (7)	−0.0064 (7)	0.0032 (6)	0.0005 (6)
C13	0.0449 (9)	0.0397 (9)	0.0341 (7)	−0.0055 (7)	0.0001 (6)	0.0002 (6)
C14	0.0578 (11)	0.0458 (10)	0.0415 (8)	0.0020 (8)	0.0034 (7)	0.0048 (7)
C15	0.0659 (12)	0.0577 (11)	0.0409 (9)	−0.0092 (10)	0.0057 (8)	0.0086 (8)
C16	0.0481 (10)	0.0661 (12)	0.0398 (8)	−0.0115 (9)	0.0062 (7)	−0.0094 (8)
C17	0.0609 (12)	0.0533 (11)	0.0567 (10)	0.0063 (9)	0.0078 (9)	−0.0075 (9)
C18	0.0680 (12)	0.0433 (10)	0.0464 (9)	0.0020 (9)	0.0073 (8)	0.0044 (8)
C19	0.0477 (10)	0.0527 (10)	0.0410 (8)	−0.0043 (8)	0.0044 (7)	−0.0070 (8)
C20	0.0484 (10)	0.0488 (10)	0.0417 (8)	−0.0093 (8)	0.0064 (7)	−0.0020 (8)
C21	0.0423 (9)	0.0481 (10)	0.0423 (8)	−0.0095 (8)	0.0079 (7)	0.0012 (7)
C22	0.0518 (11)	0.0647 (12)	0.0581 (11)	−0.0049 (9)	0.0001 (9)	−0.0122 (10)
C23	0.0571 (13)	0.0924 (17)	0.0646 (13)	−0.0050 (12)	−0.0094 (10)	−0.0107 (12)
C24	0.0518 (12)	0.0860 (16)	0.0686 (13)	−0.0023 (12)	−0.0044 (10)	0.0138 (12)
C25	0.0580 (13)	0.0586 (12)	0.0831 (14)	0.0038 (10)	0.0100 (11)	0.0095 (11)
C26	0.0561 (12)	0.0543 (11)	0.0599 (11)	−0.0073 (9)	0.0043 (9)	−0.0038 (9)
O1	0.0640 (9)	0.0567 (9)	0.0663 (8)	0.0095 (7)	−0.0058 (7)	−0.0002 (7)
O2	0.0662 (9)	0.0488 (8)	0.0732 (9)	−0.0011 (7)	−0.0107 (7)	−0.0074 (7)
F1	0.0872 (8)	0.0500 (6)	0.0693 (7)	0.0144 (6)	0.0138 (6)	0.0116 (6)
Cl1	0.0771 (4)	0.1152 (5)	0.0580 (3)	−0.0121 (3)	0.0268 (3)	−0.0149 (3)

C1—C2	1.476 (7)	C10—H10	0.9300
C1—C3	1.515 (7)	C11—F1	1.3615 (19)
C1—H1A	0.9700	C12—C19	1.523 (2)
C1—H1B	0.9700	C12—C13	1.524 (2)
C2—C3	1.499 (5)	C12—H12	0.9800
C2—H2A	0.9700	C13—C18	1.385 (2)
C2—H2B	0.9700	C13—C14	1.384 (2)
C3—C4	1.463 (4)	C14—C15	1.390 (2)
C3—H3	0.9800	C14—H14	0.9300
C1'—C2'	1.475 (9)	C15—C16	1.369 (3)
C1'—C3'	1.516 (8)	C15—H15	0.9300
C1'—H1'1	0.9700	C16—C17	1.373 (3)
C1'—H1'2	0.9700	C16—Cl1	1.7371 (17)
C2'—C3'	1.505 (9)	C17—C18	1.379 (3)
C2'—H2'1	0.9700	C17—H17	0.9300
C2'—H2'2	0.9700	C18—H18	0.9300
C3'—C4	1.458 (7)	C19—C20	1.510 (2)
C3'—H3'	0.9800	C19—H19A	0.9700
C4—O1	1.214 (2)	C19—H19B	0.9700
C4—C5	1.521 (2)	C20—O2	1.216 (2)
C5—C6	1.528 (2)	C20—C21	1.491 (2)
C5—C12	1.550 (2)	C21—C26	1.387 (3)
C5—H5	0.9800	C21—C22	1.388 (2)
C6—C11	1.378 (2)	C22—C23	1.372 (3)
C6—C7	1.393 (2)	C22—H22	0.9300
C7—C8	1.387 (2)	C23—C24	1.368 (3)
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.373 (3)	C24—C25	1.370 (3)
C8—H8	0.9300	C24—H24	0.9300
C9—C10	1.375 (3)	C25—C26	1.385 (3)
C9—H9	0.9300	C25—H25	0.9300
C10—C11	1.377 (2)	C26—H26	0.9300
C2—C1—C3	60.1 (3)	C10—C9—H9	120.1
C2—C1—H1A	117.8	C9—C10—C11	118.67 (17)
C3—C1—H1A	117.8	C9—C10—H10	120.7
C2—C1—H1B	117.8	C11—C10—H10	120.7
C3—C1—H1B	117.8	F1—C11—C10	117.53 (16)
H1A—C1—H1B	114.9	F1—C11—C6	118.65 (14)
C1—C2—C3	61.2 (3)	C10—C11—C6	123.81 (16)
C1—C2—H2A	117.6	C19—C12—C13	112.05 (13)
C3—C2—H2A	117.6	C19—C12—C5	110.16 (13)
C1—C2—H2B	117.6	C13—C12—C5	111.07 (13)
C3—C2—H2B	117.6	C19—C12—H12	107.8
H2A—C2—H2B	114.8	C13—C12—H12	107.8
C4—C3—C2	119.0 (6)	C5—C12—H12	107.8
C4—C3—C1	113.3 (6)	C18—C13—C14	117.70 (15)
C2—C3—C1	58.6 (3)	C18—C13—C12	120.29 (14)
C4—C3—H3	117.5	C14—C13—C12	122.00 (15)
C2—C3—H3	117.5	C13—C14—C15	121.21 (17)
C1—C3—H3	117.5	C13—C14—H14	119.4
C2'—C1'—C3'	60.4 (4)	C15—C14—H14	119.4
C2'—C1'—H1'1	117.7	C16—C15—C14	119.26 (17)
C3'—C1'—H1'1	117.7	C16—C15—H15	120.4
C2'—C1'—H1'2	117.7	C14—C15—H15	120.4
C3'—C1'—H1'2	117.7	C15—C16—C17	120.91 (16)
H1'1—C1'—H1'2	114.9	C15—C16—Cl1	120.03 (15)
C1'—C2'—C3'	61.2 (4)	C17—C16—Cl1	119.04 (16)
C1'—C2'—H2'1	117.7	C16—C17—C18	119.19 (18)
C3'—C2'—H2'1	117.7	C16—C17—H17	120.4
C1'—C2'—H2'2	117.7	C18—C17—H17	120.4
C3'—C2'—H2'2	117.7	C17—C18—C13	121.73 (17)
H2'1—C2'—H2'2	114.8	C17—C18—H18	119.1
C4—C3'—C2'	117.6 (13)	C13—C18—H18	119.1
C4—C3'—C1'	119.1 (10)	C20—C19—C12	114.19 (15)
C2'—C3'—C1'	58.4 (4)	C20—C19—H19A	108.7
C4—C3'—H3'	116.4	C12—C19—H19A	108.7
C2'—C3'—H3'	116.4	C20—C19—H19B	108.7
C1'—C3'—H3'	116.4	C12—C19—H19B	108.7
O1—C4—C3'	119.4 (7)	H19A—C19—H19B	107.6
O1—C4—C3	124.0 (3)	O2—C20—C21	120.46 (16)
O1—C4—C5	120.85 (16)	O2—C20—C19	121.01 (17)
C3'—C4—C5	119.7 (7)	C21—C20—C19	118.53 (15)
C3—C4—C5	115.1 (3)	C26—C21—C22	118.03 (17)
C4—C5—C6	108.84 (12)	C26—C21—C20	123.26 (16)
C4—C5—C12	111.47 (14)	C22—C21—C20	118.70 (16)
C6—C5—C12	113.19 (13)	C23—C22—C21	121.0 (2)
C4—C5—H5	107.7	C23—C22—H22	119.5
C6—C5—H5	107.7	C21—C22—H22	119.5
C12—C5—H5	107.7	C24—C23—C22	120.4 (2)
C11—C6—C7	115.96 (15)	C24—C23—H23	119.8
C11—C6—C5	121.87 (14)	C22—C23—H23	119.8
C7—C6—C5	122.16 (15)	C23—C24—C25	119.8 (2)
C8—C7—C6	121.44 (17)	C23—C24—H24	120.1
C8—C7—H7	119.3	C25—C24—H24	120.1
C6—C7—H7	119.3	C24—C25—C26	120.2 (2)
C9—C8—C7	120.20 (17)	C24—C25—H25	119.9
C9—C8—H8	119.9	C26—C25—H25	119.9
C7—C8—H8	119.9	C25—C26—C21	120.50 (19)
C8—C9—C10	119.89 (16)	C25—C26—H26	119.7
C8—C9—H9	120.1	C21—C26—H26	119.7
C1—C2—C3—C4	101.0 (8)	C5—C6—C11—C10	−177.77 (16)
C2—C1—C3—C4	−110.8 (7)	C4—C5—C12—C19	−174.70 (13)
C1'—C2'—C3'—C4	108.8 (13)	C6—C5—C12—C19	62.20 (17)
C2'—C1'—C3'—C4	−106.3 (17)	C4—C5—C12—C13	−49.96 (18)
C2'—C3'—C4—O1	−23 (2)	C6—C5—C12—C13	−173.05 (13)
C1'—C3'—C4—O1	44 (2)	C19—C12—C13—C18	−133.75 (17)
C2'—C3'—C4—C3	155 (17)	C5—C12—C13—C18	102.58 (18)
C1'—C3'—C4—C3	−138 (17)	C19—C12—C13—C14	46.9 (2)
C2'—C3'—C4—C5	158.4 (12)	C5—C12—C13—C14	−76.75 (19)
C1'—C3'—C4—C5	−134.2 (14)	C18—C13—C14—C15	0.7 (3)
C2—C3—C4—O1	1.1 (11)	C12—C13—C14—C15	−179.92 (16)
C1—C3—C4—O1	66.9 (9)	C13—C14—C15—C16	−0.8 (3)
C2—C3—C4—C3'	−1 (15)	C14—C15—C16—C17	0.1 (3)
C1—C3—C4—C3'	64 (15)	C14—C15—C16—Cl1	178.20 (14)
C2—C3—C4—C5	−177.9 (7)	C15—C16—C17—C18	0.6 (3)
C1—C3—C4—C5	−112.0 (7)	Cl1—C16—C17—C18	−177.55 (15)
O1—C4—C5—C6	86.48 (19)	C16—C17—C18—C13	−0.6 (3)
C3'—C4—C5—C6	−94.9 (9)	C14—C13—C18—C17	−0.1 (3)
C3—C4—C5—C6	−94.5 (5)	C12—C13—C18—C17	−179.41 (17)
O1—C4—C5—C12	−39.1 (2)	C13—C12—C19—C20	59.33 (19)
C3'—C4—C5—C12	139.6 (9)	C5—C12—C19—C20	−176.48 (13)
C3—C4—C5—C12	139.9 (5)	C12—C19—C20—O2	18.5 (2)
C4—C5—C6—C11	133.68 (16)	C12—C19—C20—C21	−162.26 (14)
C12—C5—C6—C11	−101.78 (18)	O2—C20—C21—C26	166.47 (17)
C4—C5—C6—C7	−45.1 (2)	C19—C20—C21—C26	−12.7 (2)
C12—C5—C6—C7	79.41 (19)	O2—C20—C21—C22	−12.5 (3)
C11—C6—C7—C8	−0.3 (2)	C19—C20—C21—C22	168.31 (16)
C5—C6—C7—C8	178.58 (15)	C26—C21—C22—C23	−0.6 (3)
C6—C7—C8—C9	−0.5 (3)	C20—C21—C22—C23	178.36 (19)
C7—C8—C9—C10	0.6 (3)	C21—C22—C23—C24	−1.1 (3)
C8—C9—C10—C11	0.2 (3)	C22—C23—C24—C25	1.8 (3)
C9—C10—C11—F1	177.85 (16)	C23—C24—C25—C26	−0.8 (3)
C9—C10—C11—C6	−1.1 (3)	C24—C25—C26—C21	−1.0 (3)
C7—C6—C11—F1	−177.82 (15)	C22—C21—C26—C25	1.7 (3)
C5—C6—C11—F1	3.3 (2)	C20—C21—C26—C25	−177.30 (17)
C7—C6—C11—C10	1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···F1i	0.98	2.52	3.440 (2)	155
C5—H5···F1	0.98	2.41	2.840 (2)	106
C7—H7···O1	0.93	2.57	3.152 (2)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯F1i	0.98	2.52	3.440 (2)	155
C7—H7⋯O1	0.93	2.57	3.152 (2)	121

Symmetry code: (i) .