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

In the title compound, C(16)H(10)ClF(3)O(3), the two benzene rings are slightly twisted from each other, with a dihedral angle of 15.50 (8)° between the planes. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into a layer parallel to the bc plane.

Related literature

For the background and applications of phenacyl benzoates, see: Sheehan & Umezaw (1973 ▶); Ruzicka et al. (2002 ▶); Litera et al. (2006 ▶); Rather & Reid (1919 ▶); Huang et al. (1996 ▶); Gandhi et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H10ClF3O3

M = 342.69

Monoclinic,

a = 14.3036 (7) Å

b = 12.1335 (6) Å

c = 8.5464 (4) Å

β = 101.444 (1)°

V = 1453.76 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 100 K

0.28 × 0.16 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.919, T max = 0.966

15629 measured reflections

3822 independent reflections

2963 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.121

S = 1.04

3822 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.33 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/S1600536811020629/is2720sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020629/is2720Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020629/is2720Isup3.cml

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

C16H10ClF3O3	F(000) = 696
Mr = 342.69	Dx = 1.566 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3750 reflections
a = 14.3036 (7) Å	θ = 2.9–29.9°
b = 12.1335 (6) Å	µ = 0.31 mm−1
c = 8.5464 (4) Å	T = 100 K
β = 101.444 (1)°	Block, colourless
V = 1453.76 (12) Å3	0.28 × 0.16 × 0.11 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3822 independent reflections
Radiation source: fine-focus sealed tube	2963 reflections with I > 2σ(I)
graphite	Rint = 0.046
φ and ω scans	θmax = 29.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
Tmin = 0.919, Tmax = 0.966	k = −10→16
15629 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0486P)2 + 1.0347P] where P = (Fo2 + 2Fc2)/3
3822 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	0.22643 (4)	0.86068 (4)	1.07291 (6)	0.02896 (14)
F1	0.92991 (14)	0.87892 (13)	0.01853 (17)	0.0580 (5)
F2	1.04777 (11)	0.85923 (17)	0.2147 (2)	0.0727 (6)
F3	0.93614 (10)	0.73951 (11)	0.17107 (16)	0.0371 (3)
O1	0.53911 (10)	1.07226 (11)	0.66621 (15)	0.0222 (3)
O2	0.66428 (9)	0.93394 (11)	0.59360 (15)	0.0214 (3)
O3	0.69311 (10)	0.76708 (11)	0.49795 (17)	0.0260 (3)
C1	0.43295 (14)	0.83441 (15)	0.8232 (2)	0.0202 (4)
H1A	0.4678	0.7774	0.7845	0.024*
C2	0.36390 (14)	0.80774 (16)	0.9092 (2)	0.0225 (4)
H2A	0.3509	0.7329	0.9297	0.027*
C3	0.31378 (14)	0.89225 (16)	0.9650 (2)	0.0207 (4)
C4	0.33093 (13)	1.00257 (16)	0.9356 (2)	0.0202 (4)
H4A	0.2957	1.0593	0.9742	0.024*
C5	0.39992 (13)	1.02787 (15)	0.8495 (2)	0.0191 (4)
H5A	0.4122	1.1028	0.8285	0.023*
C6	0.45214 (13)	0.94487 (15)	0.7924 (2)	0.0171 (4)
C7	0.52797 (13)	0.97681 (15)	0.7041 (2)	0.0182 (4)
C8	0.59082 (14)	0.88503 (15)	0.6632 (2)	0.0199 (4)
H8A	0.6195	0.8437	0.7609	0.024*
H8B	0.5526	0.8332	0.5868	0.024*
C9	0.71079 (13)	0.86489 (15)	0.5125 (2)	0.0190 (4)
C10	0.78492 (13)	0.92229 (15)	0.4433 (2)	0.0185 (4)
C11	0.80562 (14)	1.03401 (16)	0.4691 (2)	0.0219 (4)
H11A	0.7732	1.0758	0.5358	0.026*
C12	0.87340 (15)	1.08395 (17)	0.3975 (3)	0.0276 (4)
H12A	0.8872	1.1601	0.4149	0.033*
C13	0.92112 (15)	1.02351 (17)	0.3007 (2)	0.0264 (4)
H13A	0.9673	1.0580	0.2511	0.032*
C14	0.90109 (14)	0.91177 (17)	0.2764 (2)	0.0228 (4)
C15	0.83340 (13)	0.86101 (16)	0.3467 (2)	0.0198 (4)
H15A	0.8200	0.7848	0.3292	0.024*
C16	0.95338 (16)	0.84786 (19)	0.1713 (3)	0.0314 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0281 (3)	0.0281 (3)	0.0351 (3)	−0.0017 (2)	0.0170 (2)	0.0031 (2)
F1	0.1082 (15)	0.0398 (9)	0.0358 (8)	0.0034 (9)	0.0380 (9)	−0.0024 (6)
F2	0.0272 (8)	0.0992 (15)	0.0989 (14)	−0.0158 (8)	0.0301 (8)	−0.0676 (12)
F3	0.0439 (8)	0.0256 (7)	0.0466 (8)	0.0074 (6)	0.0204 (6)	−0.0064 (6)
O1	0.0289 (7)	0.0134 (6)	0.0255 (6)	−0.0011 (5)	0.0082 (6)	0.0029 (5)
O2	0.0242 (7)	0.0165 (6)	0.0263 (6)	−0.0022 (5)	0.0121 (5)	−0.0020 (5)
O3	0.0311 (8)	0.0137 (6)	0.0362 (8)	−0.0031 (6)	0.0140 (6)	−0.0030 (6)
C1	0.0241 (9)	0.0131 (9)	0.0243 (9)	0.0023 (7)	0.0070 (7)	0.0001 (7)
C2	0.0257 (10)	0.0162 (9)	0.0272 (9)	0.0001 (7)	0.0088 (8)	0.0023 (7)
C3	0.0212 (9)	0.0214 (9)	0.0210 (8)	−0.0017 (7)	0.0078 (7)	0.0011 (7)
C4	0.0214 (9)	0.0167 (9)	0.0219 (8)	0.0035 (7)	0.0030 (7)	−0.0010 (7)
C5	0.0224 (9)	0.0140 (8)	0.0199 (8)	0.0012 (7)	0.0020 (7)	0.0013 (7)
C6	0.0200 (9)	0.0140 (8)	0.0175 (7)	−0.0005 (7)	0.0039 (6)	0.0007 (7)
C7	0.0212 (9)	0.0153 (8)	0.0173 (8)	−0.0007 (7)	0.0021 (7)	0.0010 (7)
C8	0.0232 (9)	0.0152 (9)	0.0225 (8)	−0.0007 (7)	0.0074 (7)	0.0011 (7)
C9	0.0203 (9)	0.0170 (9)	0.0200 (8)	0.0011 (7)	0.0046 (7)	−0.0008 (7)
C10	0.0186 (9)	0.0156 (9)	0.0214 (8)	0.0003 (7)	0.0038 (7)	0.0018 (7)
C11	0.0227 (9)	0.0175 (9)	0.0268 (9)	0.0015 (7)	0.0078 (7)	−0.0019 (7)
C12	0.0265 (10)	0.0168 (10)	0.0413 (11)	−0.0027 (8)	0.0112 (9)	−0.0028 (8)
C13	0.0249 (10)	0.0237 (10)	0.0323 (10)	−0.0034 (8)	0.0100 (8)	0.0020 (8)
C14	0.0210 (9)	0.0238 (10)	0.0246 (9)	0.0010 (8)	0.0068 (7)	−0.0039 (8)
C15	0.0216 (9)	0.0161 (9)	0.0219 (8)	0.0000 (7)	0.0043 (7)	−0.0014 (7)
C16	0.0298 (11)	0.0325 (12)	0.0356 (11)	−0.0061 (9)	0.0155 (9)	−0.0119 (9)

Cl1—C3	1.7364 (19)	C5—H5A	0.9500
F1—C16	1.336 (3)	C6—C7	1.490 (3)
F2—C16	1.335 (3)	C7—C8	1.515 (3)
F3—C16	1.338 (3)	C8—H8A	0.9900
O1—C7	1.222 (2)	C8—H8B	0.9900
O2—C9	1.344 (2)	C9—C10	1.486 (3)
O2—C8	1.435 (2)	C10—C15	1.394 (3)
O3—C9	1.215 (2)	C10—C11	1.396 (3)
C1—C2	1.381 (3)	C11—C12	1.385 (3)
C1—C6	1.403 (3)	C11—H11A	0.9500
C1—H1A	0.9500	C12—C13	1.383 (3)
C2—C3	1.389 (3)	C12—H12A	0.9500
C2—H2A	0.9500	C13—C14	1.393 (3)
C3—C4	1.393 (3)	C13—H13A	0.9500
C4—C5	1.378 (3)	C14—C15	1.381 (3)
C4—H4A	0.9500	C14—C16	1.495 (3)
C5—C6	1.398 (3)	C15—H15A	0.9500
C9—O2—C8	115.72 (14)	O3—C9—O2	123.20 (17)
C2—C1—C6	120.70 (17)	O3—C9—C10	124.57 (17)
C2—C1—H1A	119.6	O2—C9—C10	112.22 (16)
C6—C1—H1A	119.6	C15—C10—C11	119.79 (17)
C1—C2—C3	118.83 (18)	C15—C10—C9	117.65 (17)
C1—C2—H2A	120.6	C11—C10—C9	122.55 (17)
C3—C2—H2A	120.6	C12—C11—C10	120.03 (18)
C2—C3—C4	121.75 (18)	C12—C11—H11A	120.0
C2—C3—Cl1	119.64 (15)	C10—C11—H11A	120.0
C4—C3—Cl1	118.61 (15)	C13—C12—C11	120.28 (19)
C5—C4—C3	118.75 (17)	C13—C12—H12A	119.9
C5—C4—H4A	120.6	C11—C12—H12A	119.9
C3—C4—H4A	120.6	C12—C13—C14	119.61 (19)
C4—C5—C6	120.98 (17)	C12—C13—H13A	120.2
C4—C5—H5A	119.5	C14—C13—H13A	120.2
C6—C5—H5A	119.5	C15—C14—C13	120.71 (18)
C5—C6—C1	118.99 (17)	C15—C14—C16	120.48 (19)
C5—C6—C7	118.83 (16)	C13—C14—C16	118.80 (18)
C1—C6—C7	122.16 (16)	C14—C15—C10	119.58 (18)
O1—C7—C6	121.81 (17)	C14—C15—H15A	120.2
O1—C7—C8	121.41 (17)	C10—C15—H15A	120.2
C6—C7—C8	116.78 (15)	F2—C16—F1	106.7 (2)
O2—C8—C7	107.97 (14)	F2—C16—F3	106.1 (2)
O2—C8—H8A	110.1	F1—C16—F3	105.40 (17)
C7—C8—H8A	110.1	F2—C16—C14	112.24 (17)
O2—C8—H8B	110.1	F1—C16—C14	112.5 (2)
C7—C8—H8B	110.1	F3—C16—C14	113.35 (18)
H8A—C8—H8B	108.4
C6—C1—C2—C3	−0.1 (3)	O2—C9—C10—C15	−175.47 (15)
C1—C2—C3—C4	0.5 (3)	O3—C9—C10—C11	−177.10 (18)
C1—C2—C3—Cl1	179.84 (15)	O2—C9—C10—C11	3.2 (2)
C2—C3—C4—C5	−0.4 (3)	C15—C10—C11—C12	0.7 (3)
Cl1—C3—C4—C5	−179.73 (14)	C9—C10—C11—C12	−178.00 (18)
C3—C4—C5—C6	−0.1 (3)	C10—C11—C12—C13	−0.2 (3)
C4—C5—C6—C1	0.4 (3)	C11—C12—C13—C14	−0.4 (3)
C4—C5—C6—C7	−178.17 (16)	C12—C13—C14—C15	0.7 (3)
C2—C1—C6—C5	−0.3 (3)	C12—C13—C14—C16	179.9 (2)
C2—C1—C6—C7	178.24 (17)	C13—C14—C15—C10	−0.2 (3)
C5—C6—C7—O1	−7.6 (2)	C16—C14—C15—C10	−179.49 (17)
C1—C6—C7—O1	173.85 (17)	C11—C10—C15—C14	−0.4 (3)
C5—C6—C7—C8	172.43 (16)	C9—C10—C15—C14	178.31 (16)
C1—C6—C7—C8	−6.1 (2)	C15—C14—C16—F2	−128.0 (2)
C9—O2—C8—C7	−163.11 (14)	C13—C14—C16—F2	52.7 (3)
O1—C7—C8—O2	5.7 (2)	C15—C14—C16—F1	111.7 (2)
C6—C7—C8—O2	−174.34 (14)	C13—C14—C16—F1	−67.6 (2)
C8—O2—C9—O3	−0.2 (3)	C15—C14—C16—F3	−7.8 (3)
C8—O2—C9—C10	179.50 (14)	C13—C14—C16—F3	172.98 (18)
O3—C9—C10—C15	4.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1i	0.95	2.53	3.205 (2)	128.
C4—H4A···O3ii	0.95	2.53	3.289 (2)	137.
C8—H8A···O3iii	0.99	2.48	3.474 (2)	177.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1i	0.95	2.53	3.205 (2)	128
C4—H4A⋯O3ii	0.95	2.53	3.289 (2)	137
C8—H8A⋯O3iii	0.99	2.48	3.474 (2)	177

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