2-(4-Chloro-phen-yl)-2-oxoethyl 2,4-di-fluoro-benzoate.

The asymmetric unit of title compound, C(15)H(9)ClF(2)O(3), consists of two crystallographically independent mol-ecules. The dihedral angle between the two terminal benzene rings in one mol-ecule is 7.92 (14)°, while that in the other mol-ecule is 73.50 (16)°. In the crystal, mol-ecules are stacked into columns along the b axis by inter-molecular C-H⋯O hydrogen bonds. A π-π inter-action with a centroid-to-centroid distance of 3.747 (2) Å further stabilizes the crystal structure.

Related literature

For background to and applications of phenacyl benzoates, see: Rather & Reid (1919 ▶); Sheehan & Umezaw (1973 ▶); Ruzicka et al. (2002 ▶); Litera et al. (2006 ▶); Huang et al. (1996 ▶); Gandhi et al. (1995 ▶). For reference bond-length values, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H9ClF2O3

M = 310.67

Monoclinic,

a = 16.0179 (17) Å

b = 7.9609 (8) Å

c = 24.0172 (18) Å

β = 115.939 (5)°

V = 2754.1 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.55 × 0.26 × 0.09 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.850, T max = 0.974

17424 measured reflections

6308 independent reflections

3353 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.206

S = 1.03

6308 reflections

379 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.32 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811020630/is2722sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020630/is2722Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020630/is2722Isup3.cml

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

C15H9ClF2O3	F(000) = 1264
Mr = 310.67	Dx = 1.499 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3882 reflections
a = 16.0179 (17) Å	θ = 2.6–22.5°
b = 7.9609 (8) Å	µ = 0.31 mm−1
c = 24.0172 (18) Å	T = 296 K
β = 115.939 (5)°	Needle, colourless
V = 2754.1 (5) Å3	0.55 × 0.26 × 0.09 mm
Z = 8

Bruker SMART APEXII DUO CCD area-detector diffractometer	6308 independent reflections
Radiation source: fine-focus sealed tube	3353 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→19
Tmin = 0.850, Tmax = 0.974	k = −10→10
17424 measured reflections	l = −31→31

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.114P)2 + 0.0306P] where P = (Fo2 + 2Fc2)/3
6308 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Cl1A	0.01833 (6)	0.69373 (15)	0.67059 (4)	0.1116 (4)
F1A	0.77697 (12)	0.3081 (3)	1.00087 (8)	0.1006 (6)
F2A	0.80582 (16)	−0.0433 (3)	1.16292 (10)	0.1139 (7)
O1A	0.32955 (14)	0.3728 (3)	0.93888 (9)	0.0827 (6)
O2A	0.49808 (12)	0.3539 (2)	0.95029 (8)	0.0654 (5)
O3A	0.60473 (13)	0.3792 (3)	0.91508 (8)	0.0869 (7)
C1A	0.1715 (2)	0.4728 (4)	0.83169 (14)	0.0734 (8)
H1AA	0.1615	0.4076	0.8603	0.088*
C2A	0.0965 (2)	0.5297 (4)	0.77968 (15)	0.0828 (9)
H2AA	0.0364	0.5010	0.7727	0.099*
C3A	0.11135 (19)	0.6286 (4)	0.73861 (13)	0.0718 (7)
C4A	0.1996 (2)	0.6748 (4)	0.74836 (13)	0.0710 (7)
H4AA	0.2086	0.7461	0.7208	0.085*
C5A	0.27448 (19)	0.6134 (4)	0.79980 (12)	0.0661 (7)
H5AA	0.3343	0.6413	0.8061	0.079*
C6A	0.26202 (17)	0.5109 (3)	0.84226 (11)	0.0570 (6)
C7A	0.34074 (18)	0.4379 (3)	0.89723 (11)	0.0589 (6)
C8A	0.43456 (17)	0.4445 (3)	0.89777 (11)	0.0608 (6)
H8AA	0.4319	0.3949	0.8601	0.073*
H8AB	0.4547	0.5603	0.8999	0.073*
C9A	0.58203 (18)	0.3275 (3)	0.95319 (11)	0.0590 (6)
C10A	0.64078 (17)	0.2283 (3)	1.00863 (11)	0.0573 (6)
C11A	0.73636 (19)	0.2215 (4)	1.03031 (12)	0.0667 (7)
C12A	0.7933 (2)	0.1312 (4)	1.08180 (13)	0.0754 (8)
H12A	0.8572	0.1285	1.0954	0.091*
C13A	0.7515 (2)	0.0455 (4)	1.11226 (13)	0.0760 (8)
C14A	0.6584 (2)	0.0462 (4)	1.09386 (13)	0.0758 (8)
H14A	0.6325	−0.0152	1.1154	0.091*
C15A	0.6027 (2)	0.1400 (3)	1.04240 (12)	0.0649 (7)
H15A	0.5390	0.1444	1.0301	0.078*
Cl1B	−0.01753 (7)	1.09979 (18)	0.57396 (5)	0.1307 (5)
F1B	0.70241 (15)	1.0849 (3)	0.83037 (10)	0.1280 (9)
F2B	0.92324 (16)	0.8868 (4)	1.01835 (10)	0.1338 (8)
O1B	0.41561 (18)	1.1476 (3)	0.79738 (10)	0.1000 (7)
O2B	0.54117 (14)	0.9566 (3)	0.78473 (8)	0.0834 (6)
O3B	0.49789 (16)	0.8028 (3)	0.84487 (11)	0.1036 (8)
C1B	0.2248 (3)	1.1648 (4)	0.71976 (14)	0.0828 (9)
H1BA	0.2467	1.2199	0.7577	0.099*
C2B	0.1322 (3)	1.1733 (5)	0.67968 (16)	0.0935 (10)
H2BA	0.0915	1.2341	0.6902	0.112*
C3B	0.1000 (2)	1.0906 (4)	0.62378 (13)	0.0838 (9)
C4B	0.1590 (2)	1.0031 (4)	0.60703 (12)	0.0816 (9)
H4BA	0.1365	0.9495	0.5688	0.098*
C5B	0.2515 (2)	0.9953 (4)	0.64709 (11)	0.0717 (7)
H5BA	0.2916	0.9357	0.6358	0.086*
C6B	0.2865 (2)	1.0750 (3)	0.70449 (11)	0.0644 (7)
C7B	0.3848 (2)	1.0667 (3)	0.74964 (12)	0.0696 (7)
C8B	0.4479 (2)	0.9489 (5)	0.73696 (12)	0.0805 (9)
H8BA	0.4248	0.8350	0.7339	0.097*
H8BB	0.4475	0.9778	0.6976	0.097*
C9B	0.5572 (2)	0.8795 (4)	0.83760 (13)	0.0702 (7)
C10B	0.65445 (19)	0.8922 (3)	0.88491 (12)	0.0629 (7)
C11B	0.7239 (2)	0.9844 (4)	0.88009 (13)	0.0757 (8)
C12B	0.8133 (2)	0.9838 (5)	0.92315 (15)	0.0882 (9)
H12B	0.8582	1.0466	0.9179	0.106*
C13B	0.8352 (2)	0.8877 (5)	0.97465 (14)	0.0862 (9)
C14B	0.7698 (3)	0.7944 (4)	0.98378 (14)	0.0864 (9)
H14B	0.7858	0.7300	1.0193	0.104*
C15B	0.6810 (2)	0.8001 (4)	0.93878 (13)	0.0757 (8)
H15B	0.6359	0.7390	0.9445	0.091*

	U11	U22	U33	U12	U13	U23
Cl1A	0.0784 (6)	0.1292 (9)	0.1112 (7)	0.0192 (5)	0.0266 (5)	0.0172 (6)
F1A	0.0685 (11)	0.1358 (18)	0.1080 (13)	−0.0061 (10)	0.0484 (10)	0.0250 (11)
F2A	0.1271 (17)	0.1155 (17)	0.1067 (13)	0.0402 (13)	0.0580 (13)	0.0393 (12)
O1A	0.0813 (13)	0.0993 (16)	0.0837 (12)	−0.0051 (11)	0.0511 (11)	0.0162 (11)
O2A	0.0666 (11)	0.0714 (12)	0.0692 (10)	0.0014 (9)	0.0398 (9)	0.0027 (9)
O3A	0.0691 (12)	0.130 (2)	0.0746 (11)	−0.0026 (11)	0.0432 (10)	0.0174 (11)
C1A	0.0694 (18)	0.0748 (19)	0.0922 (18)	−0.0099 (15)	0.0504 (16)	0.0013 (15)
C2A	0.0612 (17)	0.091 (2)	0.107 (2)	−0.0066 (15)	0.0467 (17)	0.0037 (18)
C3A	0.0655 (17)	0.0686 (18)	0.0827 (17)	0.0034 (14)	0.0337 (14)	−0.0080 (14)
C4A	0.0788 (19)	0.0675 (18)	0.0772 (16)	0.0013 (14)	0.0437 (15)	0.0051 (14)
C5A	0.0656 (16)	0.0652 (17)	0.0790 (16)	−0.0064 (13)	0.0420 (14)	−0.0023 (13)
C6A	0.0631 (15)	0.0524 (14)	0.0665 (13)	−0.0075 (11)	0.0386 (12)	−0.0110 (11)
C7A	0.0722 (17)	0.0505 (14)	0.0670 (14)	−0.0098 (12)	0.0426 (13)	−0.0107 (12)
C8A	0.0652 (16)	0.0622 (16)	0.0629 (13)	−0.0041 (12)	0.0352 (12)	−0.0022 (12)
C9A	0.0619 (15)	0.0620 (16)	0.0619 (13)	−0.0168 (12)	0.0352 (12)	−0.0134 (12)
C10A	0.0647 (15)	0.0523 (15)	0.0632 (13)	−0.0099 (12)	0.0356 (12)	−0.0121 (11)
C11A	0.0684 (17)	0.0688 (18)	0.0739 (15)	−0.0073 (14)	0.0414 (14)	−0.0037 (13)
C12A	0.0723 (18)	0.078 (2)	0.0825 (17)	0.0069 (15)	0.0396 (15)	−0.0008 (15)
C13A	0.096 (2)	0.0638 (18)	0.0739 (16)	0.0151 (16)	0.0419 (16)	0.0045 (14)
C14A	0.099 (2)	0.0632 (18)	0.0848 (18)	−0.0055 (16)	0.0580 (18)	0.0019 (15)
C15A	0.0722 (17)	0.0585 (16)	0.0745 (15)	−0.0096 (13)	0.0416 (14)	−0.0075 (13)
Cl1B	0.0942 (7)	0.1856 (13)	0.1040 (7)	0.0478 (7)	0.0356 (6)	0.0041 (7)
F1B	0.1063 (16)	0.154 (2)	0.1211 (15)	−0.0321 (14)	0.0474 (13)	0.0536 (14)
F2B	0.0901 (15)	0.181 (2)	0.1081 (15)	−0.0141 (15)	0.0231 (13)	0.0130 (15)
O1B	0.1165 (19)	0.0871 (16)	0.0938 (15)	−0.0155 (13)	0.0435 (14)	−0.0334 (12)
O2B	0.0794 (14)	0.1104 (17)	0.0709 (11)	−0.0151 (12)	0.0426 (11)	−0.0034 (11)
O3B	0.0879 (16)	0.0978 (17)	0.1253 (18)	−0.0294 (13)	0.0468 (14)	0.0205 (14)
C1B	0.109 (3)	0.075 (2)	0.0801 (18)	0.0001 (17)	0.0553 (19)	−0.0151 (15)
C2B	0.106 (3)	0.095 (3)	0.096 (2)	0.026 (2)	0.059 (2)	−0.0040 (19)
C3B	0.085 (2)	0.097 (2)	0.0764 (17)	0.0228 (17)	0.0423 (16)	0.0098 (16)
C4B	0.087 (2)	0.102 (2)	0.0608 (15)	0.0152 (17)	0.0365 (16)	−0.0038 (15)
C5B	0.085 (2)	0.078 (2)	0.0655 (15)	0.0082 (15)	0.0451 (15)	−0.0012 (13)
C6B	0.0864 (19)	0.0554 (16)	0.0664 (14)	−0.0021 (13)	0.0472 (14)	0.0018 (12)
C7B	0.093 (2)	0.0588 (17)	0.0702 (15)	−0.0190 (14)	0.0481 (16)	−0.0099 (13)
C8B	0.077 (2)	0.103 (2)	0.0665 (15)	−0.0066 (16)	0.0357 (15)	−0.0138 (15)
C9B	0.0790 (19)	0.0623 (17)	0.0821 (17)	−0.0141 (15)	0.0470 (15)	−0.0104 (14)
C10B	0.0774 (18)	0.0541 (16)	0.0727 (15)	−0.0107 (13)	0.0473 (14)	−0.0084 (12)
C11B	0.089 (2)	0.0713 (19)	0.0778 (17)	−0.0086 (16)	0.0466 (17)	0.0091 (15)
C12B	0.080 (2)	0.100 (3)	0.094 (2)	−0.0243 (18)	0.0477 (18)	−0.0006 (19)
C13B	0.075 (2)	0.103 (3)	0.0771 (18)	−0.0093 (18)	0.0295 (16)	−0.0089 (17)
C14B	0.107 (3)	0.086 (2)	0.0711 (17)	−0.0115 (19)	0.0433 (18)	0.0055 (16)
C15B	0.095 (2)	0.0682 (19)	0.0792 (17)	−0.0194 (15)	0.0523 (17)	−0.0038 (14)

Cl1A—C3A	1.740 (3)	Cl1B—C3B	1.735 (3)
F1A—C11A	1.342 (3)	F1B—C11B	1.351 (3)
F2A—C13A	1.346 (3)	F2B—C13B	1.340 (4)
O1A—C7A	1.207 (3)	O1B—C7B	1.216 (3)
O2A—C9A	1.332 (3)	O2B—C9B	1.330 (3)
O2A—C8A	1.423 (3)	O2B—C8B	1.432 (3)
O3A—C9A	1.196 (3)	O3B—C9B	1.204 (3)
C1A—C2A	1.377 (4)	C1B—C2B	1.372 (5)
C1A—C6A	1.392 (4)	C1B—C6B	1.393 (4)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.362 (4)	C2B—C3B	1.377 (5)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.378 (4)	C3B—C4B	1.368 (4)
C4A—C5A	1.381 (4)	C4B—C5B	1.370 (4)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.387 (3)	C5B—C6B	1.393 (3)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.488 (4)	C6B—C7B	1.472 (4)
C7A—C8A	1.498 (3)	C7B—C8B	1.504 (4)
C8A—H8AA	0.9700	C8B—H8BA	0.9700
C8A—H8AB	0.9700	C8B—H8BB	0.9700
C9A—C10A	1.479 (4)	C9B—C10B	1.477 (4)
C10A—C11A	1.386 (4)	C10B—C11B	1.380 (4)
C10A—C15A	1.399 (3)	C10B—C15B	1.382 (4)
C11A—C12A	1.375 (4)	C11B—C12B	1.350 (4)
C12A—C13A	1.370 (4)	C12B—C13B	1.363 (4)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.357 (4)	C13B—C14B	1.378 (5)
C14A—C15A	1.384 (4)	C14B—C15B	1.360 (4)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C9A—O2A—C8A	116.13 (18)	C9B—O2B—C8B	116.3 (2)
C2A—C1A—C6A	121.3 (3)	C2B—C1B—C6B	121.0 (3)
C2A—C1A—H1AA	119.3	C2B—C1B—H1BA	119.5
C6A—C1A—H1AA	119.3	C6B—C1B—H1BA	119.5
C3A—C2A—C1A	119.2 (3)	C1B—C2B—C3B	119.3 (3)
C3A—C2A—H2AA	120.4	C1B—C2B—H2BA	120.4
C1A—C2A—H2AA	120.4	C3B—C2B—H2BA	120.4
C2A—C3A—C4A	121.5 (3)	C4B—C3B—C2B	121.2 (3)
C2A—C3A—Cl1A	120.2 (2)	C4B—C3B—Cl1B	120.0 (2)
C4A—C3A—Cl1A	118.3 (2)	C2B—C3B—Cl1B	118.8 (2)
C3A—C4A—C5A	118.8 (3)	C3B—C4B—C5B	119.4 (3)
C3A—C4A—H4AA	120.6	C3B—C4B—H4BA	120.3
C5A—C4A—H4AA	120.6	C5B—C4B—H4BA	120.3
C4A—C5A—C6A	121.2 (2)	C4B—C5B—C6B	121.2 (3)
C4A—C5A—H5AA	119.4	C4B—C5B—H5BA	119.4
C6A—C5A—H5AA	119.4	C6B—C5B—H5BA	119.4
C5A—C6A—C1A	117.9 (3)	C1B—C6B—C5B	118.0 (3)
C5A—C6A—C7A	122.9 (2)	C1B—C6B—C7B	118.9 (2)
C1A—C6A—C7A	119.2 (2)	C5B—C6B—C7B	123.1 (2)
O1A—C7A—C6A	121.8 (2)	O1B—C7B—C6B	122.2 (3)
O1A—C7A—C8A	121.3 (2)	O1B—C7B—C8B	119.3 (3)
C6A—C7A—C8A	116.85 (19)	C6B—C7B—C8B	118.4 (2)
O2A—C8A—C7A	108.40 (19)	O2B—C8B—C7B	111.6 (2)
O2A—C8A—H8AA	110.0	O2B—C8B—H8BA	109.3
C7A—C8A—H8AA	110.0	C7B—C8B—H8BA	109.3
O2A—C8A—H8AB	110.0	O2B—C8B—H8BB	109.3
C7A—C8A—H8AB	110.0	C7B—C8B—H8BB	109.3
H8AA—C8A—H8AB	108.4	H8BA—C8B—H8BB	108.0
O3A—C9A—O2A	122.9 (2)	O3B—C9B—O2B	122.5 (3)
O3A—C9A—C10A	125.9 (2)	O3B—C9B—C10B	123.8 (3)
O2A—C9A—C10A	111.19 (19)	O2B—C9B—C10B	113.6 (2)
C11A—C10A—C15A	116.9 (2)	C11B—C10B—C15B	115.6 (3)
C11A—C10A—C9A	121.5 (2)	C11B—C10B—C9B	126.2 (2)
C15A—C10A—C9A	121.5 (2)	C15B—C10B—C9B	118.2 (2)
F1A—C11A—C12A	117.3 (2)	C12B—C11B—F1B	117.0 (3)
F1A—C11A—C10A	119.5 (2)	C12B—C11B—C10B	123.9 (3)
C12A—C11A—C10A	123.2 (2)	F1B—C11B—C10B	119.1 (3)
C13A—C12A—C11A	117.0 (3)	C11B—C12B—C13B	117.6 (3)
C13A—C12A—H12A	121.5	C11B—C12B—H12B	121.2
C11A—C12A—H12A	121.5	C13B—C12B—H12B	121.2
F2A—C13A—C14A	118.7 (3)	F2B—C13B—C12B	118.6 (3)
F2A—C13A—C12A	118.1 (3)	F2B—C13B—C14B	119.0 (3)
C14A—C13A—C12A	123.2 (3)	C12B—C13B—C14B	122.3 (3)
C13A—C14A—C15A	118.7 (3)	C15B—C14B—C13B	117.3 (3)
C13A—C14A—H14A	120.7	C15B—C14B—H14B	121.3
C15A—C14A—H14A	120.7	C13B—C14B—H14B	121.3
C14A—C15A—C10A	121.0 (3)	C14B—C15B—C10B	123.3 (3)
C14A—C15A—H15A	119.5	C14B—C15B—H15B	118.4
C10A—C15A—H15A	119.5	C10B—C15B—H15B	118.4
C6A—C1A—C2A—C3A	−1.6 (5)	C6B—C1B—C2B—C3B	0.4 (5)
C1A—C2A—C3A—C4A	−0.9 (5)	C1B—C2B—C3B—C4B	−1.3 (5)
C1A—C2A—C3A—Cl1A	176.8 (2)	C1B—C2B—C3B—Cl1B	179.1 (3)
C2A—C3A—C4A—C5A	2.6 (4)	C2B—C3B—C4B—C5B	1.1 (5)
Cl1A—C3A—C4A—C5A	−175.1 (2)	Cl1B—C3B—C4B—C5B	−179.3 (3)
C3A—C4A—C5A—C6A	−1.8 (4)	C3B—C4B—C5B—C6B	−0.1 (5)
C4A—C5A—C6A—C1A	−0.5 (4)	C2B—C1B—C6B—C5B	0.5 (4)
C4A—C5A—C6A—C7A	178.1 (2)	C2B—C1B—C6B—C7B	−178.6 (3)
C2A—C1A—C6A—C5A	2.3 (4)	C4B—C5B—C6B—C1B	−0.7 (4)
C2A—C1A—C6A—C7A	−176.4 (3)	C4B—C5B—C6B—C7B	178.4 (3)
C5A—C6A—C7A—O1A	167.5 (2)	C1B—C6B—C7B—O1B	−6.7 (4)
C1A—C6A—C7A—O1A	−13.9 (4)	C5B—C6B—C7B—O1B	174.1 (3)
C5A—C6A—C7A—C8A	−14.2 (3)	C1B—C6B—C7B—C8B	170.9 (3)
C1A—C6A—C7A—C8A	164.4 (2)	C5B—C6B—C7B—C8B	−8.2 (4)
C9A—O2A—C8A—C7A	171.1 (2)	C9B—O2B—C8B—C7B	75.9 (3)
O1A—C7A—C8A—O2A	4.4 (3)	O1B—C7B—C8B—O2B	−2.8 (4)
C6A—C7A—C8A—O2A	−173.96 (19)	C6B—C7B—C8B—O2B	179.4 (2)
C8A—O2A—C9A—O3A	1.6 (4)	C8B—O2B—C9B—O3B	2.2 (4)
C8A—O2A—C9A—C10A	−178.4 (2)	C8B—O2B—C9B—C10B	−179.9 (2)
O3A—C9A—C10A—C11A	16.9 (4)	O3B—C9B—C10B—C11B	−176.8 (3)
O2A—C9A—C10A—C11A	−163.1 (2)	O2B—C9B—C10B—C11B	5.3 (4)
O3A—C9A—C10A—C15A	−164.6 (3)	O3B—C9B—C10B—C15B	5.4 (4)
O2A—C9A—C10A—C15A	15.4 (3)	O2B—C9B—C10B—C15B	−172.5 (2)
C15A—C10A—C11A—F1A	−177.9 (2)	C15B—C10B—C11B—C12B	2.1 (4)
C9A—C10A—C11A—F1A	0.7 (4)	C9B—C10B—C11B—C12B	−175.8 (3)
C15A—C10A—C11A—C12A	1.1 (4)	C15B—C10B—C11B—F1B	−176.4 (3)
C9A—C10A—C11A—C12A	179.7 (2)	C9B—C10B—C11B—F1B	5.7 (4)
F1A—C11A—C12A—C13A	178.9 (3)	F1B—C11B—C12B—C13B	177.6 (3)
C10A—C11A—C12A—C13A	−0.2 (4)	C10B—C11B—C12B—C13B	−0.9 (5)
C11A—C12A—C13A—F2A	−179.8 (2)	C11B—C12B—C13B—F2B	−179.2 (3)
C11A—C12A—C13A—C14A	0.1 (4)	C11B—C12B—C13B—C14B	−0.5 (5)
F2A—C13A—C14A—C15A	178.8 (2)	F2B—C13B—C14B—C15B	179.2 (3)
C12A—C13A—C14A—C15A	−1.1 (4)	C12B—C13B—C14B—C15B	0.5 (5)
C13A—C14A—C15A—C10A	2.1 (4)	C13B—C14B—C15B—C10B	0.9 (5)
C11A—C10A—C15A—C14A	−2.1 (4)	C11B—C10B—C15B—C14B	−2.1 (4)
C9A—C10A—C15A—C14A	179.4 (2)	C9B—C10B—C15B—C14B	176.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8A—H8AB···O3B	0.97	2.60	3.451 (4)	147.
C8A—H8AA···O1Bi	0.97	2.42	3.294 (3)	149.
C5B—H5BA···O3Aii	0.93	2.50	3.376 (4)	158.
C8B—H8BB···O3Aii	0.97	2.58	3.415 (3)	144.
C14B—H14B···O1Aiii	0.93	2.59	3.216 (5)	125.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8A—H8AB⋯O3B	0.97	2.60	3.451 (4)	147
C8A—H8AA⋯O1Bi	0.97	2.42	3.294 (3)	149
C5B—H5BA⋯O3Aii	0.93	2.50	3.376 (4)	158
C8B—H8BB⋯O3Aii	0.97	2.58	3.415 (3)	144
C14B—H14B⋯O1Aiii	0.93	2.59	3.216 (5)	125

Symmetry codes: (i) ; (ii) ; (iii) .