2-(4-Fluoro-phen-yl)-2-oxoethyl 3-(trifluoro-meth-yl)benzoate.

In the title compound, C(16)H(10)F(4)O(3), the fluoro-form group is disordered over two orientations with an occupancy ratio of 0.834 (4):0.166 (4). The dihedral angle between the two aromatic rings is 20.34 (9)°. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into layers lying parallel to the bc plane.

Related literature

For background to the chemistry of phenacyl benzoate deriv­atives, see: Huang et al. (1996 ▶); Gandhi et al. (1995 ▶); Ruzicka et al. (2002 ▶); Litera et al. (2006 ▶); Sheehan & Umezaw (1973 ▶). For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Fun et al. (2011 ▶).

Experimental

Crystal data

C16H10F4O3

M = 326.24

Monoclinic,

a = 14.7694 (19) Å

b = 12.1602 (16) Å

c = 8.0929 (10) Å

β = 95.886 (2)°

V = 1445.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 296 K

0.38 × 0.25 × 0.07 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.950, T max = 0.990

18790 measured reflections

4815 independent reflections

2841 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.182

S = 1.04

4815 reflections

221 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.35 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: SHELXTLand PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103947X/hb6418sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103947X/hb6418Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103947X/hb6418Isup3.cml

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

C16H10F4O3	F(000) = 664
Mr = 326.24	Dx = 1.499 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4165 reflections
a = 14.7694 (19) Å	θ = 2.2–27.2°
b = 12.1602 (16) Å	µ = 0.14 mm−1
c = 8.0929 (10) Å	T = 296 K
β = 95.886 (2)°	Block, colourless
V = 1445.8 (3) Å3	0.38 × 0.25 × 0.07 mm
Z = 4

Bruker SMART APEXII DUO CCD diffractometer	4815 independent reflections
Radiation source: fine-focus sealed tube	2841 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 31.6°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→21
Tmin = 0.950, Tmax = 0.990	k = −17→17
18790 measured reflections	l = −11→11

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0745P)2 + 0.3289P] where P = (Fo2 + 2Fc2)/3
4815 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.35 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	Occ. (<1)
F1	0.41559 (16)	0.37665 (19)	−0.5044 (2)	0.1144 (9)	0.834 (4)
F2	0.44559 (19)	0.25120 (16)	−0.3326 (4)	0.1179 (11)	0.834 (4)
F3	0.53719 (16)	0.3931 (3)	−0.3405 (5)	0.1359 (12)	0.834 (4)
F1X	0.5096 (11)	0.4001 (13)	−0.4146 (18)	0.110 (5)*	0.166 (4)
F2X	0.4251 (10)	0.2913 (17)	−0.413 (2)	0.137 (6)*	0.166 (4)
F3X	0.5187 (7)	0.2898 (8)	−0.2308 (12)	0.096 (3)*	0.166 (4)
F4	−0.27124 (10)	0.35096 (15)	0.5827 (2)	0.1118 (6)
O1	0.18686 (10)	0.27074 (10)	−0.0004 (2)	0.0756 (4)
O2	0.15270 (8)	0.43444 (10)	0.10304 (15)	0.0578 (3)
O3	0.02656 (9)	0.56904 (9)	0.18644 (16)	0.0623 (3)
C1	−0.11779 (12)	0.51838 (14)	0.3751 (2)	0.0522 (4)
H1A	−0.1071	0.5922	0.3543	0.063*
C2	−0.18848 (13)	0.48938 (17)	0.4648 (2)	0.0628 (5)
H2A	−0.2257	0.5427	0.5050	0.075*
C3	−0.20243 (14)	0.38007 (19)	0.4931 (3)	0.0707 (5)
C4	−0.14948 (14)	0.29857 (17)	0.4363 (3)	0.0720 (5)
H4A	−0.1609	0.2250	0.4577	0.086*
C5	−0.07894 (13)	0.32825 (14)	0.3467 (2)	0.0577 (4)
H5A	−0.0423	0.2741	0.3071	0.069*
C6	−0.06199 (11)	0.43833 (12)	0.31499 (18)	0.0447 (3)
C7	0.01478 (11)	0.47363 (12)	0.22220 (19)	0.0458 (3)
C8	0.07752 (12)	0.38408 (13)	0.1730 (2)	0.0523 (4)
H8A	0.0994	0.3408	0.2696	0.063*
H8B	0.0451	0.3356	0.0921	0.063*
C9	0.20286 (12)	0.36718 (13)	0.0189 (2)	0.0520 (4)
C10	0.27900 (11)	0.42548 (13)	−0.0491 (2)	0.0502 (4)
C11	0.30026 (13)	0.53430 (15)	−0.0112 (3)	0.0658 (5)
H11A	0.2676	0.5727	0.0624	0.079*
C12	0.36985 (16)	0.58564 (18)	−0.0826 (3)	0.0818 (7)
H12A	0.3833	0.6589	−0.0581	0.098*
C13	0.41962 (15)	0.52905 (18)	−0.1900 (3)	0.0753 (6)
H13A	0.4665	0.5639	−0.2379	0.090*
C14	0.39943 (13)	0.42070 (16)	−0.2259 (2)	0.0604 (4)
C15	0.32944 (12)	0.36853 (14)	−0.1566 (2)	0.0550 (4)
H15A	0.3161	0.2953	−0.1820	0.066*
C16	0.45169 (18)	0.3601 (2)	−0.3439 (4)	0.0866 (7)

	U11	U22	U33	U12	U13	U23
F1	0.153 (2)	0.1219 (18)	0.0750 (12)	0.0103 (13)	0.0431 (12)	−0.0150 (11)
F2	0.162 (2)	0.0723 (12)	0.1333 (19)	0.0433 (13)	0.0827 (18)	0.0078 (12)
F3	0.0656 (13)	0.194 (3)	0.156 (3)	−0.0032 (14)	0.0486 (15)	−0.064 (2)
F4	0.0863 (10)	0.1217 (13)	0.1375 (13)	−0.0144 (9)	0.0607 (9)	0.0101 (10)
O1	0.0871 (10)	0.0428 (7)	0.1035 (11)	−0.0067 (6)	0.0413 (8)	−0.0073 (7)
O2	0.0601 (7)	0.0439 (6)	0.0729 (8)	−0.0040 (5)	0.0234 (6)	−0.0052 (5)
O3	0.0732 (8)	0.0360 (6)	0.0797 (8)	−0.0019 (5)	0.0170 (6)	0.0077 (5)
C1	0.0571 (9)	0.0416 (8)	0.0576 (9)	0.0070 (7)	0.0040 (7)	−0.0007 (7)
C2	0.0567 (10)	0.0668 (12)	0.0655 (10)	0.0109 (9)	0.0099 (8)	−0.0044 (9)
C3	0.0556 (11)	0.0800 (14)	0.0791 (13)	−0.0082 (10)	0.0185 (9)	0.0035 (10)
C4	0.0748 (13)	0.0512 (10)	0.0933 (14)	−0.0120 (9)	0.0253 (11)	0.0056 (10)
C5	0.0640 (10)	0.0377 (8)	0.0735 (11)	−0.0022 (7)	0.0171 (8)	−0.0004 (7)
C6	0.0494 (8)	0.0350 (7)	0.0493 (8)	0.0001 (6)	0.0033 (6)	0.0004 (6)
C7	0.0542 (9)	0.0338 (7)	0.0491 (8)	−0.0008 (6)	0.0042 (6)	0.0008 (6)
C8	0.0580 (9)	0.0404 (8)	0.0606 (9)	−0.0023 (7)	0.0164 (7)	0.0015 (7)
C9	0.0572 (9)	0.0425 (8)	0.0574 (9)	0.0022 (7)	0.0117 (7)	0.0004 (7)
C10	0.0503 (9)	0.0429 (8)	0.0581 (9)	0.0028 (6)	0.0090 (7)	0.0009 (7)
C11	0.0630 (11)	0.0483 (9)	0.0894 (13)	−0.0005 (8)	0.0236 (10)	−0.0124 (9)
C12	0.0803 (14)	0.0515 (11)	0.1196 (18)	−0.0159 (10)	0.0387 (13)	−0.0176 (11)
C13	0.0658 (12)	0.0634 (12)	0.1012 (16)	−0.0088 (10)	0.0307 (11)	−0.0018 (11)
C14	0.0562 (10)	0.0586 (10)	0.0685 (11)	0.0035 (8)	0.0172 (8)	−0.0001 (8)
C15	0.0596 (10)	0.0446 (8)	0.0623 (10)	0.0038 (7)	0.0129 (8)	−0.0012 (7)
C16	0.0847 (16)	0.0780 (16)	0.1050 (19)	−0.0056 (13)	0.0472 (14)	−0.0146 (14)

F1—C16	1.368 (4)	C5—C6	1.391 (2)
F2—C16	1.331 (3)	C5—H5A	0.9300
F3—C16	1.323 (3)	C6—C7	1.486 (2)
F1X—C16	1.182 (16)	C7—C8	1.510 (2)
F2X—C16	1.059 (17)	C8—H8A	0.9700
F3X—C16	1.537 (10)	C8—H8B	0.9700
F4—C3	1.355 (2)	C9—C10	1.482 (2)
O1—C9	1.203 (2)	C10—C11	1.387 (2)
O2—C9	1.336 (2)	C10—C15	1.387 (2)
O2—C8	1.4342 (19)	C11—C12	1.379 (3)
O3—C7	1.2126 (18)	C11—H11A	0.9300
C1—C2	1.377 (3)	C12—C13	1.379 (3)
C1—C6	1.395 (2)	C12—H12A	0.9300
C1—H1A	0.9300	C13—C14	1.375 (3)
C2—C3	1.368 (3)	C13—H13A	0.9300
C2—H2A	0.9300	C14—C15	1.380 (2)
C3—C4	1.371 (3)	C14—C16	1.484 (3)
C4—C5	1.377 (3)	C15—H15A	0.9300
C4—H4A	0.9300
C9—O2—C8	115.59 (13)	C12—C11—C10	120.07 (17)
C2—C1—C6	120.80 (16)	C12—C11—H11A	120.0
C2—C1—H1A	119.6	C10—C11—H11A	120.0
C6—C1—H1A	119.6	C13—C12—C11	120.44 (18)
C3—C2—C1	118.20 (17)	C13—C12—H12A	119.8
C3—C2—H2A	120.9	C11—C12—H12A	119.8
C1—C2—H2A	120.9	C14—C13—C12	119.56 (19)
F4—C3—C2	118.5 (2)	C14—C13—H13A	120.2
F4—C3—C4	118.41 (19)	C12—C13—H13A	120.2
C2—C3—C4	123.04 (18)	C13—C14—C15	120.65 (18)
C3—C4—C5	118.40 (18)	C13—C14—C16	119.73 (19)
C3—C4—H4A	120.8	C15—C14—C16	119.59 (19)
C5—C4—H4A	120.8	C14—C15—C10	119.88 (16)
C4—C5—C6	120.66 (17)	C14—C15—H15A	120.1
C4—C5—H5A	119.7	C10—C15—H15A	120.1
C6—C5—H5A	119.7	F2X—C16—F1X	108.5 (12)
C5—C6—C1	118.91 (15)	F2X—C16—F3	123.5 (9)
C5—C6—C7	122.18 (14)	F1X—C16—F2	120.0 (8)
C1—C6—C7	118.90 (14)	F3—C16—F2	111.8 (3)
O3—C7—C6	122.18 (14)	F2X—C16—F1	61.8 (11)
O3—C7—C8	121.35 (14)	F1X—C16—F1	73.2 (7)
C6—C7—C8	116.47 (12)	F3—C16—F1	104.7 (3)
O2—C8—C7	108.49 (12)	F2—C16—F1	100.9 (3)
O2—C8—H8A	110.0	F2X—C16—C14	122.9 (9)
C7—C8—H8A	110.0	F1X—C16—C14	123.9 (8)
O2—C8—H8B	110.0	F3—C16—C14	113.3 (2)
C7—C8—H8B	110.0	F2—C16—C14	114.0 (2)
H8A—C8—H8B	108.4	F1—C16—C14	111.1 (2)
O1—C9—O2	123.44 (16)	F2X—C16—F3X	93.2 (11)
O1—C9—C10	124.35 (16)	F1X—C16—F3X	93.6 (8)
O2—C9—C10	112.20 (14)	F3—C16—F3X	66.5 (4)
C11—C10—C15	119.39 (16)	F2—C16—F3X	56.6 (4)
C11—C10—C9	122.52 (15)	F1—C16—F3X	144.3 (4)
C15—C10—C9	118.08 (15)	C14—C16—F3X	103.9 (4)
C6—C1—C2—C3	0.0 (3)	C15—C10—C11—C12	1.2 (3)
C1—C2—C3—F4	179.32 (18)	C9—C10—C11—C12	−177.7 (2)
C1—C2—C3—C4	−0.1 (3)	C10—C11—C12—C13	−0.9 (4)
F4—C3—C4—C5	−179.30 (19)	C11—C12—C13—C14	0.0 (4)
C2—C3—C4—C5	0.1 (3)	C12—C13—C14—C15	0.6 (3)
C3—C4—C5—C6	0.0 (3)	C12—C13—C14—C16	178.9 (2)
C4—C5—C6—C1	−0.1 (3)	C13—C14—C15—C10	−0.3 (3)
C4—C5—C6—C7	178.56 (17)	C16—C14—C15—C10	−178.6 (2)
C2—C1—C6—C5	0.2 (2)	C11—C10—C15—C14	−0.6 (3)
C2—C1—C6—C7	−178.58 (15)	C9—C10—C15—C14	178.38 (16)
C5—C6—C7—O3	175.79 (16)	C13—C14—C16—F2X	−154.8 (13)
C1—C6—C7—O3	−5.5 (2)	C15—C14—C16—F2X	23.5 (14)
C5—C6—C7—C8	−3.7 (2)	C13—C14—C16—F1X	−2.1 (9)
C1—C6—C7—C8	174.96 (14)	C15—C14—C16—F1X	176.3 (9)
C9—O2—C8—C7	−165.10 (14)	C13—C14—C16—F3	32.0 (4)
O3—C7—C8—O2	7.2 (2)	C15—C14—C16—F3	−149.7 (3)
C6—C7—C8—O2	−173.24 (13)	C13—C14—C16—F2	161.3 (3)
C8—O2—C9—O1	0.9 (3)	C15—C14—C16—F2	−20.3 (4)
C8—O2—C9—C10	−179.97 (14)	C13—C14—C16—F1	−85.5 (3)
O1—C9—C10—C11	−173.9 (2)	C15—C14—C16—F1	92.9 (3)
O2—C9—C10—C11	7.0 (2)	C13—C14—C16—F3X	102.0 (5)
O1—C9—C10—C15	7.2 (3)	C15—C14—C16—F3X	−79.6 (5)
O2—C9—C10—C15	−171.99 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O3i	0.93	2.50	3.263 (2)	139
C8—H8A···O1ii	0.97	2.55	3.502 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O3i	0.93	2.50	3.263 (2)	139
C8—H8A⋯O1ii	0.97	2.55	3.502 (2)	169

Symmetry codes: (i) ; (ii) .