Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-1-(4-bromo­phen­yl)-3-(3-fluoro­phen­yl)prop-2-en-1-one

The title halogenated organic chalcone was prepared by a Claisen–Schmidt condensation reaction. A Hirshfeld surface analysis was carried out to reveal the percentage contributions of the inter­molecular inter­actions. A theoretical study was performed using the density functional theory (DFT) at B3LYP with the 6–311 G++(d,p) basis set level to compare with the experimental results of the X-ray analysis and UV–vis absorption analysis in term of the geometrical parameters, HOMO-LUMO energy gap and charge distributions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.158
• Data-to-parameter ratio = 22.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.332 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         24 Report
PLAT922_ALERT_1_C wR2 in the CIF and FCF Differ by ...............    -0.0018 Check
PLAT923_ALERT_1_C S    Values in the CIF and FCF Differ by .......     -0.012 Check
PLAT927_ALERT_1_C Reported and Calculated  wR2 Differ by .........    -0.0026 Check
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as      mixed Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br1A     ..Br1B             3.60 Ang.
                                               -1-x,1-y,1-z  =      2_466 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         12 Note
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2018 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         44 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

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

(E)-1-(4-Bromophenyl)-3-(3-fluorophenyl)prop-2-en-1-one

Crystal data

C15H10BrFO	Z = 4
Mr = 305.14	F(000) = 608
Triclinic, P1	Dx = 1.579 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0090 (4) Å	Cell parameters from 8958 reflections
b = 10.8695 (7) Å	θ = 2.5–28.0°
c = 20.5616 (12) Å	µ = 3.20 mm^−1
α = 102.803 (1)°	T = 296 K
β = 96.938 (1)°	Plate, yellow
γ = 97.276 (1)°	0.56 × 0.39 × 0.29 mm
V = 1283.57 (14) Å^3

Data collection

Bruker SMART APEXII Duo CCD area-detector diffractometer	7437 independent reflections
Radiation source: fine-focus sealed tube	4832 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.267, Tmax = 0.455	k = −15→15
27389 measured reflections	l = −28→28

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0792P)^2 + 0.4733P] where P = (Fo^2 + 2Fc^2)/3
7437 reflections	(Δ/σ)max = 0.001
325 parameters	Δρmax = 0.85 e Å^−3
0 restraints	Δρmin = −1.35 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1A	−0.36851 (7)	1.01488 (4)	0.369778 (19)	0.07958 (15)
F1A	0.5304 (4)	0.3263 (2)	0.74576 (11)	0.0894 (7)
O1A	0.3367 (4)	0.6239 (3)	0.46486 (13)	0.0805 (8)
C1A	−0.1316 (5)	0.7958 (3)	0.49478 (14)	0.0533 (6)
H1AA	−0.1703	0.7725	0.5333	0.064*
C2A	−0.2576 (5)	0.8732 (3)	0.46588 (16)	0.0595 (7)
H2AA	−0.3807	0.9017	0.4846	0.071*
C3A	−0.1989 (5)	0.9074 (3)	0.40938 (15)	0.0564 (7)
C4A	−0.0175 (6)	0.8661 (3)	0.38068 (16)	0.0632 (8)
H4AA	0.0205	0.8903	0.3423	0.076*
C5A	0.1071 (5)	0.7882 (3)	0.40975 (15)	0.0583 (7)
H5AA	0.2293	0.7596	0.3906	0.070*
C6A	0.0523 (4)	0.7524 (2)	0.46713 (13)	0.0462 (5)
C7A	0.1930 (5)	0.6668 (3)	0.49525 (14)	0.0526 (6)
C8A	0.1559 (5)	0.6354 (3)	0.55997 (14)	0.0513 (6)
H8AA	0.0430	0.6682	0.5824	0.062*
C9A	0.2801 (5)	0.5616 (3)	0.58648 (13)	0.0492 (6)
H9AA	0.3932	0.5324	0.5628	0.059*
C10A	0.2592 (5)	0.5208 (2)	0.64885 (12)	0.0457 (5)
C11A	0.4081 (5)	0.4430 (3)	0.66883 (14)	0.0531 (6)
H11A	0.5195	0.4181	0.6433	0.064*
C12A	0.3866 (6)	0.4042 (3)	0.72699 (15)	0.0606 (7)
C13A	0.2265 (6)	0.4381 (3)	0.76688 (15)	0.0685 (9)
H13A	0.2171	0.4102	0.8062	0.082*
C14A	0.0807 (7)	0.5147 (4)	0.74667 (17)	0.0750 (9)
H14A	−0.0297	0.5390	0.7727	0.090*
C15A	0.0953 (6)	0.5562 (3)	0.68819 (15)	0.0637 (8)
H15A	−0.0050	0.6080	0.6752	0.076*
Br1B	−0.33082 (7)	−0.20429 (4)	0.72238 (2)	0.09061 (17)
F1B	1.2882 (4)	0.0939 (2)	1.06936 (14)	0.1021 (8)
O1B	0.3006 (4)	0.34757 (19)	0.91642 (11)	0.0632 (5)
C1B	−0.0157 (5)	0.1510 (3)	0.83454 (15)	0.0538 (6)
H1BA	−0.0513	0.2333	0.8440	0.065*
C2B	−0.1694 (5)	0.0535 (3)	0.79170 (15)	0.0587 (7)
H2BA	−0.3074	0.0694	0.7722	0.070*
C3B	−0.1153 (5)	−0.0677 (3)	0.77835 (16)	0.0590 (7)
C4B	0.0883 (6)	−0.0930 (3)	0.80586 (19)	0.0730 (9)
H4BA	0.1231	−0.1754	0.7959	0.088*
C5B	0.2415 (5)	0.0063 (3)	0.84882 (17)	0.0646 (8)
H5BA	0.3799	−0.0101	0.8677	0.077*
C6B	0.1921 (5)	0.1289 (3)	0.86397 (13)	0.0484 (6)
C7B	0.3501 (5)	0.2405 (2)	0.90990 (13)	0.0483 (6)
C8B	0.5623 (5)	0.2192 (3)	0.94716 (14)	0.0522 (6)
H8BA	0.6019	0.1378	0.9396	0.063*
C9B	0.6961 (5)	0.3151 (3)	0.99126 (13)	0.0481 (5)
H9BA	0.6479	0.3943	0.9971	0.058*
C10B	0.9115 (5)	0.3113 (2)	1.03206 (12)	0.0458 (5)
C11B	0.9974 (5)	0.1983 (3)	1.03227 (15)	0.0574 (7)
H11B	0.9164	0.1202	1.0071	0.069*
C12B	1.2032 (6)	0.2045 (3)	1.07027 (16)	0.0623 (7)
C13B	1.3312 (5)	0.3157 (3)	1.10868 (15)	0.0611 (7)
H13B	1.4703	0.3159	1.1341	0.073*
C14B	1.2459 (6)	0.4271 (3)	1.10829 (14)	0.0607 (7)
H14B	1.3291	0.5046	1.1335	0.073*
C15B	1.0377 (5)	0.4254 (3)	1.07085 (13)	0.0527 (6)
H15B	0.9816	0.5016	1.0717	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1A	0.0856 (3)	0.0670 (2)	0.0818 (3)	0.01918 (18)	−0.02313 (19)	0.02390 (17)
F1A	0.1164 (18)	0.0866 (14)	0.0753 (13)	0.0378 (13)	−0.0027 (12)	0.0375 (11)
O1A	0.0840 (17)	0.1058 (19)	0.0857 (16)	0.0548 (15)	0.0438 (14)	0.0557 (15)
C1A	0.0548 (15)	0.0585 (16)	0.0497 (14)	0.0147 (12)	0.0070 (12)	0.0166 (12)
C2A	0.0569 (16)	0.0606 (17)	0.0612 (16)	0.0184 (13)	0.0026 (13)	0.0134 (13)
C3A	0.0599 (16)	0.0471 (14)	0.0552 (15)	0.0058 (12)	−0.0141 (13)	0.0115 (11)
C4A	0.073 (2)	0.0651 (18)	0.0542 (16)	0.0068 (15)	0.0018 (14)	0.0268 (14)
C5A	0.0599 (17)	0.0622 (17)	0.0578 (16)	0.0161 (13)	0.0103 (13)	0.0206 (13)
C6A	0.0467 (13)	0.0440 (12)	0.0471 (13)	0.0050 (10)	0.0029 (10)	0.0128 (10)
C7A	0.0535 (15)	0.0521 (14)	0.0570 (15)	0.0134 (12)	0.0103 (12)	0.0191 (12)
C8A	0.0537 (15)	0.0519 (14)	0.0521 (14)	0.0143 (12)	0.0119 (12)	0.0153 (11)
C9A	0.0504 (14)	0.0487 (13)	0.0495 (13)	0.0093 (11)	0.0076 (11)	0.0129 (11)
C10A	0.0509 (14)	0.0421 (12)	0.0417 (12)	0.0054 (10)	0.0032 (10)	0.0083 (10)
C11A	0.0605 (16)	0.0479 (13)	0.0482 (14)	0.0101 (12)	0.0009 (12)	0.0090 (11)
C12A	0.075 (2)	0.0516 (15)	0.0514 (15)	0.0051 (13)	−0.0077 (14)	0.0159 (12)
C13A	0.083 (2)	0.078 (2)	0.0440 (15)	0.0016 (17)	0.0046 (15)	0.0221 (14)
C14A	0.077 (2)	0.098 (3)	0.0557 (17)	0.021 (2)	0.0217 (16)	0.0213 (18)
C15A	0.071 (2)	0.0728 (19)	0.0533 (16)	0.0248 (16)	0.0120 (14)	0.0185 (14)
Br1B	0.0727 (3)	0.0615 (2)	0.1139 (3)	0.01018 (17)	−0.0328 (2)	−0.00307 (19)
F1B	0.0907 (16)	0.0653 (13)	0.140 (2)	0.0298 (11)	−0.0343 (15)	0.0209 (13)
O1B	0.0684 (13)	0.0461 (10)	0.0725 (13)	0.0170 (9)	−0.0053 (10)	0.0128 (9)
C1B	0.0542 (16)	0.0488 (13)	0.0599 (15)	0.0171 (11)	0.0020 (12)	0.0147 (12)
C2B	0.0498 (15)	0.0613 (17)	0.0632 (17)	0.0151 (13)	−0.0054 (13)	0.0153 (13)
C3B	0.0537 (16)	0.0529 (15)	0.0638 (16)	0.0070 (12)	−0.0068 (13)	0.0091 (13)
C4B	0.0655 (19)	0.0492 (16)	0.093 (2)	0.0170 (14)	−0.0145 (17)	0.0023 (15)
C5B	0.0523 (16)	0.0541 (16)	0.081 (2)	0.0168 (13)	−0.0117 (14)	0.0102 (14)
C6B	0.0473 (13)	0.0519 (14)	0.0472 (13)	0.0113 (11)	0.0024 (11)	0.0151 (11)
C7B	0.0513 (14)	0.0462 (13)	0.0483 (13)	0.0105 (11)	0.0034 (11)	0.0138 (10)
C8B	0.0528 (15)	0.0472 (13)	0.0567 (15)	0.0134 (11)	0.0017 (12)	0.0134 (11)
C9B	0.0520 (14)	0.0462 (13)	0.0477 (13)	0.0114 (11)	0.0055 (11)	0.0135 (10)
C10B	0.0506 (14)	0.0462 (13)	0.0410 (12)	0.0097 (10)	0.0056 (10)	0.0112 (10)
C11B	0.0600 (16)	0.0450 (13)	0.0626 (16)	0.0068 (12)	−0.0056 (13)	0.0125 (12)
C12B	0.0648 (18)	0.0560 (16)	0.0659 (17)	0.0164 (14)	−0.0031 (14)	0.0176 (14)
C13B	0.0552 (16)	0.0719 (19)	0.0547 (15)	0.0077 (14)	−0.0022 (13)	0.0190 (14)
C14B	0.0633 (18)	0.0603 (17)	0.0484 (14)	0.0039 (13)	−0.0039 (13)	0.0017 (12)
C15B	0.0635 (17)	0.0485 (14)	0.0438 (13)	0.0121 (12)	0.0054 (12)	0.0060 (11)

Geometric parameters (Å, º)

Br1A—C3A	1.894 (3)	Br1B—C3B	1.898 (3)
F1A—C12A	1.365 (4)	F1B—C12B	1.362 (4)
O1A—C7A	1.207 (4)	O1B—C7B	1.221 (3)
C1A—C2A	1.381 (4)	C1B—C2B	1.376 (4)
C1A—C6A	1.390 (4)	C1B—C6B	1.393 (4)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.367 (5)	C2B—C3B	1.374 (4)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.378 (5)	C3B—C4B	1.371 (4)
C4A—C5A	1.383 (4)	C4B—C5B	1.386 (4)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.385 (4)	C5B—C6B	1.379 (4)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.494 (4)	C6B—C7B	1.499 (4)
C7A—C8A	1.481 (4)	C7B—C8B	1.477 (4)
C8A—C9A	1.321 (4)	C8B—C9B	1.322 (4)
C8A—H8AA	0.9300	C8B—H8BA	0.9300
C9A—C10A	1.461 (4)	C9B—C10B	1.465 (4)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—C15A	1.387 (4)	C10B—C15B	1.388 (4)
C10A—C11A	1.393 (4)	C10B—C11B	1.393 (4)
C11A—C12A	1.368 (4)	C11B—C12B	1.366 (4)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.371 (5)	C12B—C13B	1.368 (5)
C13A—C14A	1.373 (5)	C13B—C14B	1.375 (5)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.383 (5)	C14B—C15B	1.383 (4)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C2A—C1A—C6A	121.0 (3)	C2B—C1B—C6B	121.4 (3)
C2A—C1A—H1AA	119.5	C2B—C1B—H1BA	119.3
C6A—C1A—H1AA	119.5	C6B—C1B—H1BA	119.3
C3A—C2A—C1A	119.1 (3)	C3B—C2B—C1B	118.8 (3)
C3A—C2A—H2AA	120.4	C3B—C2B—H2BA	120.6
C1A—C2A—H2AA	120.4	C1B—C2B—H2BA	120.6
C2A—C3A—C4A	121.4 (3)	C4B—C3B—C2B	121.6 (3)
C2A—C3A—Br1A	119.5 (2)	C4B—C3B—Br1B	119.2 (2)
C4A—C3A—Br1A	119.0 (2)	C2B—C3B—Br1B	119.2 (2)
C3A—C4A—C5A	119.1 (3)	C3B—C4B—C5B	118.9 (3)
C3A—C4A—H4AA	120.5	C3B—C4B—H4BA	120.5
C5A—C4A—H4AA	120.5	C5B—C4B—H4BA	120.5
C4A—C5A—C6A	120.8 (3)	C6B—C5B—C4B	121.1 (3)
C4A—C5A—H5AA	119.6	C6B—C5B—H5BA	119.5
C6A—C5A—H5AA	119.6	C4B—C5B—H5BA	119.5
C5A—C6A—C1A	118.6 (3)	C5B—C6B—C1B	118.2 (3)
C5A—C6A—C7A	117.8 (2)	C5B—C6B—C7B	123.8 (2)
C1A—C6A—C7A	123.6 (2)	C1B—C6B—C7B	118.0 (2)
O1A—C7A—C8A	120.4 (3)	O1B—C7B—C8B	120.9 (3)
O1A—C7A—C6A	119.5 (2)	O1B—C7B—C6B	119.5 (2)
C8A—C7A—C6A	120.0 (2)	C8B—C7B—C6B	119.6 (2)
C9A—C8A—C7A	121.3 (3)	C9B—C8B—C7B	120.4 (2)
C9A—C8A—H8AA	119.4	C9B—C8B—H8BA	119.8
C7A—C8A—H8AA	119.4	C7B—C8B—H8BA	119.8
C8A—C9A—C10A	127.1 (3)	C8B—C9B—C10B	127.6 (2)
C8A—C9A—H9AA	116.4	C8B—C9B—H9BA	116.2
C10A—C9A—H9AA	116.4	C10B—C9B—H9BA	116.2
C15A—C10A—C11A	119.3 (2)	C15B—C10B—C11B	118.6 (3)
C15A—C10A—C9A	122.1 (3)	C15B—C10B—C9B	118.7 (2)
C11A—C10A—C9A	118.6 (2)	C11B—C10B—C9B	122.7 (2)
C12A—C11A—C10A	118.4 (3)	C12B—C11B—C10B	118.6 (3)
C12A—C11A—H11A	120.8	C12B—C11B—H11B	120.7
C10A—C11A—H11A	120.8	C10B—C11B—H11B	120.7
F1A—C12A—C11A	118.2 (3)	F1B—C12B—C11B	118.3 (3)
F1A—C12A—C13A	118.3 (3)	F1B—C12B—C13B	117.7 (3)
C11A—C12A—C13A	123.5 (3)	C11B—C12B—C13B	123.9 (3)
C12A—C13A—C14A	117.6 (3)	C12B—C13B—C14B	117.3 (3)
C12A—C13A—H13A	121.2	C12B—C13B—H13B	121.3
C14A—C13A—H13A	121.2	C14B—C13B—H13B	121.3
C13A—C14A—C15A	121.1 (3)	C13B—C14B—C15B	120.8 (3)
C13A—C14A—H14A	119.5	C13B—C14B—H14B	119.6
C15A—C14A—H14A	119.5	C15B—C14B—H14B	119.6
C14A—C15A—C10A	120.1 (3)	C14B—C15B—C10B	120.8 (3)
C14A—C15A—H15A	119.9	C14B—C15B—H15B	119.6
C10A—C15A—H15A	119.9	C10B—C15B—H15B	119.6
C6A—C1A—C2A—C3A	−0.2 (5)	C6B—C1B—C2B—C3B	0.3 (5)
C1A—C2A—C3A—C4A	0.2 (5)	C1B—C2B—C3B—C4B	−0.9 (5)
C1A—C2A—C3A—Br1A	−179.4 (2)	C1B—C2B—C3B—Br1B	177.4 (2)
C2A—C3A—C4A—C5A	0.1 (5)	C2B—C3B—C4B—C5B	0.8 (6)
Br1A—C3A—C4A—C5A	179.6 (2)	Br1B—C3B—C4B—C5B	−177.5 (3)
C3A—C4A—C5A—C6A	−0.3 (5)	C3B—C4B—C5B—C6B	−0.1 (6)
C4A—C5A—C6A—C1A	0.3 (5)	C4B—C5B—C6B—C1B	−0.5 (5)
C4A—C5A—C6A—C7A	179.3 (3)	C4B—C5B—C6B—C7B	−179.9 (3)
C2A—C1A—C6A—C5A	0.0 (4)	C2B—C1B—C6B—C5B	0.4 (4)
C2A—C1A—C6A—C7A	−179.0 (3)	C2B—C1B—C6B—C7B	179.8 (3)
C5A—C6A—C7A—O1A	−5.7 (4)	C5B—C6B—C7B—O1B	174.3 (3)
C1A—C6A—C7A—O1A	173.3 (3)	C1B—C6B—C7B—O1B	−5.2 (4)
C5A—C6A—C7A—C8A	174.3 (3)	C5B—C6B—C7B—C8B	−6.3 (4)
C1A—C6A—C7A—C8A	−6.8 (4)	C1B—C6B—C7B—C8B	174.2 (3)
O1A—C7A—C8A—C9A	1.0 (5)	O1B—C7B—C8B—C9B	3.9 (4)
C6A—C7A—C8A—C9A	−179.0 (3)	C6B—C7B—C8B—C9B	−175.5 (3)
C7A—C8A—C9A—C10A	−178.7 (3)	C7B—C8B—C9B—C10B	−179.7 (3)
C8A—C9A—C10A—C15A	0.9 (5)	C8B—C9B—C10B—C15B	173.9 (3)
C8A—C9A—C10A—C11A	−179.6 (3)	C8B—C9B—C10B—C11B	−4.5 (5)
C15A—C10A—C11A—C12A	0.0 (4)	C15B—C10B—C11B—C12B	−0.5 (4)
C9A—C10A—C11A—C12A	−179.4 (3)	C9B—C10B—C11B—C12B	177.9 (3)
C10A—C11A—C12A—F1A	178.9 (3)	C10B—C11B—C12B—F1B	−178.9 (3)
C10A—C11A—C12A—C13A	−0.2 (5)	C10B—C11B—C12B—C13B	0.2 (5)
F1A—C12A—C13A—C14A	−178.9 (3)	F1B—C12B—C13B—C14B	178.8 (3)
C11A—C12A—C13A—C14A	0.3 (5)	C11B—C12B—C13B—C14B	−0.3 (5)
C12A—C13A—C14A—C15A	−0.1 (6)	C12B—C13B—C14B—C15B	0.6 (5)
C13A—C14A—C15A—C10A	−0.1 (6)	C13B—C14B—C15B—C10B	−0.9 (5)
C11A—C10A—C15A—C14A	0.1 (5)	C11B—C10B—C15B—C14B	0.8 (4)
C9A—C10A—C15A—C14A	179.6 (3)	C9B—C10B—C15B—C14B	−177.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13A—H13A···O1B	0.93	2.52	3.427 (4)	165
C9A—H9AA···O1A^i	0.93	2.52	3.362 (4)	151
C11A—H11A···O1A^i	0.93	2.45	3.294 (4)	151
C15B—H15B···O1B^ii	0.93	2.50	3.377 (4)	157

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2.