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

In the title compound, C(16)H(13)FO(4), the dihedral angle between the benzene rings is 84.28 (8)°. In the crystal, C-H⋯F and C-H⋯O hydrogen bonds link the mol-ecules to form a three-dimensional network. The crystal structure is consolidated by C-H⋯π inter-actions and short F⋯F contacts [2.7748 (14) Å] also occur.

Related literature

For related structures and background to phenacyl benzoates, see: Fun et al. (2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H13FO4

M = 288.26

Monoclinic,

a = 9.3523 (2) Å

b = 10.1949 (2) Å

c = 15.6465 (4) Å

β = 118.842 (2)°

V = 1306.77 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.29 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.967, T max = 0.984

18005 measured reflections

4669 independent reflections

3194 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.151

S = 1.03

4669 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.29 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/S1600536811049233/hb6504sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049233/hb6504Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811049233/hb6504Isup3.cml

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

C16H13FO4	F(000) = 600
Mr = 288.26	Dx = 1.465 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3370 reflections
a = 9.3523 (2) Å	θ = 2.5–32.1°
b = 10.1949 (2) Å	µ = 0.11 mm−1
c = 15.6465 (4) Å	T = 100 K
β = 118.842 (2)°	Block, yellow
V = 1306.77 (5) Å3	0.29 × 0.25 × 0.15 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4669 independent reflections
Radiation source: fine-focus sealed tube	3194 reflections with I > 2σ(I)
graphite	Rint = 0.061
φ and ω scans	θmax = 32.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.967, Tmax = 0.984	k = −15→10
18005 measured reflections	l = −23→23

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0735P)2 + 0.1795P] where P = (Fo2 + 2Fc2)/3
4669 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.29 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
F1	0.36713 (11)	0.06839 (8)	0.92948 (7)	0.0261 (2)
O1	0.82633 (13)	0.73381 (9)	0.99094 (8)	0.0196 (2)
O2	0.58433 (13)	0.61282 (11)	0.84358 (8)	0.0266 (3)
O3	0.94829 (13)	0.65098 (10)	0.90861 (8)	0.0242 (2)
O4	0.85652 (13)	1.24512 (10)	0.77160 (8)	0.0223 (2)
C1	0.44544 (17)	0.37022 (14)	0.84080 (11)	0.0197 (3)
H1A	0.4037	0.4188	0.7818	0.024*
C2	0.37612 (18)	0.25071 (14)	0.84149 (11)	0.0207 (3)
H2A	0.2882	0.2159	0.7837	0.025*
C3	0.43844 (18)	0.18361 (13)	0.92864 (11)	0.0192 (3)
C4	0.56758 (18)	0.22904 (14)	1.01457 (11)	0.0203 (3)
H4A	0.6071	0.1801	1.0733	0.024*
C5	0.63790 (18)	0.34841 (14)	1.01258 (11)	0.0192 (3)
H5A	0.7281	0.3810	1.0703	0.023*
C6	0.57633 (16)	0.42079 (13)	0.92587 (10)	0.0170 (3)
C7	0.64362 (17)	0.55037 (13)	0.91908 (10)	0.0176 (3)
C8	0.79205 (17)	0.60283 (13)	1.00908 (11)	0.0187 (3)
H8A	0.7709	0.6026	1.0653	0.022*
H8B	0.8874	0.5458	1.0253	0.022*
C9	0.89159 (16)	0.74423 (13)	0.93063 (10)	0.0177 (3)
C10	0.88512 (16)	0.87944 (13)	0.89496 (10)	0.0162 (3)
C11	0.96253 (17)	0.90621 (14)	0.83957 (11)	0.0186 (3)
H11A	1.0230	0.8393	0.8290	0.022*
C12	0.95157 (17)	1.02951 (14)	0.80006 (11)	0.0199 (3)
H12A	1.0049	1.0474	0.7628	0.024*
C13	0.86196 (16)	1.12769 (13)	0.81507 (10)	0.0173 (3)
C14	0.78543 (17)	1.10306 (13)	0.87092 (10)	0.0170 (3)
H14A	0.7259	1.1704	0.8818	0.020*
C15	0.79728 (16)	0.97864 (13)	0.91055 (10)	0.0170 (3)
H15A	0.7451	0.9611	0.9485	0.020*
C16	0.7667 (2)	1.34901 (14)	0.78505 (12)	0.0240 (3)
H16A	0.7724	1.4275	0.7507	0.036*
H16B	0.8136	1.3683	0.8548	0.036*
H16C	0.6525	1.3224	0.7589	0.036*

	U11	U22	U33	U12	U13	U23
F1	0.0259 (5)	0.0168 (4)	0.0324 (5)	−0.0055 (3)	0.0114 (4)	0.0027 (4)
O1	0.0248 (5)	0.0132 (4)	0.0226 (5)	−0.0019 (4)	0.0127 (4)	0.0008 (4)
O2	0.0247 (5)	0.0252 (5)	0.0243 (6)	−0.0029 (4)	0.0074 (4)	0.0073 (4)
O3	0.0250 (5)	0.0178 (5)	0.0330 (6)	0.0038 (4)	0.0166 (5)	0.0028 (4)
O4	0.0279 (6)	0.0165 (5)	0.0305 (6)	0.0026 (4)	0.0203 (5)	0.0046 (4)
C1	0.0189 (6)	0.0205 (6)	0.0190 (6)	0.0015 (5)	0.0087 (5)	0.0032 (5)
C2	0.0177 (6)	0.0206 (7)	0.0207 (7)	−0.0013 (5)	0.0068 (5)	−0.0009 (5)
C3	0.0193 (6)	0.0136 (6)	0.0261 (7)	−0.0010 (5)	0.0119 (6)	0.0000 (5)
C4	0.0227 (7)	0.0173 (6)	0.0196 (7)	0.0014 (5)	0.0091 (6)	0.0029 (5)
C5	0.0198 (6)	0.0170 (6)	0.0191 (6)	0.0002 (5)	0.0080 (5)	0.0001 (5)
C6	0.0164 (6)	0.0160 (6)	0.0203 (6)	−0.0001 (5)	0.0100 (5)	0.0006 (5)
C7	0.0167 (6)	0.0165 (6)	0.0204 (6)	0.0023 (5)	0.0096 (5)	0.0016 (5)
C8	0.0218 (6)	0.0134 (5)	0.0201 (7)	−0.0006 (5)	0.0093 (5)	0.0023 (5)
C9	0.0150 (6)	0.0164 (6)	0.0198 (6)	−0.0012 (5)	0.0069 (5)	−0.0003 (5)
C10	0.0141 (6)	0.0144 (6)	0.0181 (6)	−0.0007 (5)	0.0062 (5)	−0.0003 (5)
C11	0.0157 (6)	0.0173 (6)	0.0228 (7)	0.0002 (5)	0.0094 (5)	−0.0011 (5)
C12	0.0184 (6)	0.0205 (6)	0.0252 (7)	−0.0010 (5)	0.0140 (6)	0.0003 (6)
C13	0.0174 (6)	0.0150 (6)	0.0190 (6)	−0.0016 (5)	0.0084 (5)	0.0009 (5)
C14	0.0177 (6)	0.0150 (6)	0.0198 (6)	0.0004 (5)	0.0103 (5)	−0.0006 (5)
C15	0.0175 (6)	0.0167 (6)	0.0173 (6)	−0.0017 (5)	0.0087 (5)	−0.0008 (5)
C16	0.0302 (8)	0.0172 (6)	0.0301 (8)	0.0041 (6)	0.0188 (7)	0.0034 (6)

F1—C3	1.3541 (16)	C7—C8	1.520 (2)
O1—C9	1.3528 (18)	C8—H8A	0.9900
O1—C8	1.4333 (16)	C8—H8B	0.9900
O2—C7	1.2150 (17)	C9—C10	1.4773 (19)
O3—C9	1.2165 (17)	C10—C15	1.3966 (19)
O4—C13	1.3657 (16)	C10—C11	1.3983 (19)
O4—C16	1.4290 (18)	C11—C12	1.383 (2)
C1—C2	1.383 (2)	C11—H11A	0.9500
C1—C6	1.401 (2)	C12—C13	1.396 (2)
C1—H1A	0.9500	C12—H12A	0.9500
C2—C3	1.378 (2)	C13—C14	1.3936 (19)
C2—H2A	0.9500	C14—C15	1.3926 (19)
C3—C4	1.384 (2)	C14—H14A	0.9500
C4—C5	1.391 (2)	C15—H15A	0.9500
C4—H4A	0.9500	C16—H16A	0.9800
C5—C6	1.401 (2)	C16—H16B	0.9800
C5—H5A	0.9500	C16—H16C	0.9800
C6—C7	1.4889 (19)
C9—O1—C8	115.50 (11)	H8A—C8—H8B	108.2
C13—O4—C16	117.37 (11)	O3—C9—O1	122.76 (13)
C2—C1—C6	120.98 (13)	O3—C9—C10	124.49 (13)
C2—C1—H1A	119.5	O1—C9—C10	112.75 (12)
C6—C1—H1A	119.5	C15—C10—C11	119.40 (13)
C3—C2—C1	117.96 (14)	C15—C10—C9	122.01 (13)
C3—C2—H2A	121.0	C11—C10—C9	118.50 (12)
C1—C2—H2A	121.0	C12—C11—C10	120.38 (13)
F1—C3—C2	117.70 (13)	C12—C11—H11A	119.8
F1—C3—C4	118.95 (13)	C10—C11—H11A	119.8
C2—C3—C4	123.34 (13)	C11—C12—C13	119.84 (13)
C3—C4—C5	118.14 (13)	C11—C12—H12A	120.1
C3—C4—H4A	120.9	C13—C12—H12A	120.1
C5—C4—H4A	120.9	O4—C13—C14	124.28 (12)
C4—C5—C6	120.31 (13)	O4—C13—C12	115.20 (12)
C4—C5—H5A	119.8	C14—C13—C12	120.52 (13)
C6—C5—H5A	119.8	C15—C14—C13	119.25 (13)
C5—C6—C1	119.25 (13)	C15—C14—H14A	120.4
C5—C6—C7	123.09 (13)	C13—C14—H14A	120.4
C1—C6—C7	117.66 (12)	C14—C15—C10	120.60 (13)
O2—C7—C6	121.60 (13)	C14—C15—H15A	119.7
O2—C7—C8	120.06 (13)	C10—C15—H15A	119.7
C6—C7—C8	118.34 (12)	O4—C16—H16A	109.5
O1—C8—C7	109.63 (11)	O4—C16—H16B	109.5
O1—C8—H8A	109.7	H16A—C16—H16B	109.5
C7—C8—H8A	109.7	O4—C16—H16C	109.5
O1—C8—H8B	109.7	H16A—C16—H16C	109.5
C7—C8—H8B	109.7	H16B—C16—H16C	109.5
C6—C1—C2—C3	0.7 (2)	C8—O1—C9—C10	165.35 (11)
C1—C2—C3—F1	178.20 (13)	O3—C9—C10—C15	170.19 (14)
C1—C2—C3—C4	−0.9 (2)	O1—C9—C10—C15	−9.49 (19)
F1—C3—C4—C5	−179.17 (13)	O3—C9—C10—C11	−6.4 (2)
C2—C3—C4—C5	−0.1 (2)	O1—C9—C10—C11	173.95 (12)
C3—C4—C5—C6	1.2 (2)	C15—C10—C11—C12	−0.4 (2)
C4—C5—C6—C1	−1.3 (2)	C9—C10—C11—C12	176.28 (13)
C4—C5—C6—C7	178.76 (13)	C10—C11—C12—C13	−0.4 (2)
C2—C1—C6—C5	0.3 (2)	C16—O4—C13—C14	0.3 (2)
C2—C1—C6—C7	−179.77 (13)	C16—O4—C13—C12	−179.80 (13)
C5—C6—C7—O2	−177.62 (14)	C11—C12—C13—O4	−178.93 (13)
C1—C6—C7—O2	2.5 (2)	C11—C12—C13—C14	1.0 (2)
C5—C6—C7—C8	3.5 (2)	O4—C13—C14—C15	179.01 (13)
C1—C6—C7—C8	−176.36 (12)	C12—C13—C14—C15	−0.9 (2)
C9—O1—C8—C7	−73.21 (15)	C13—C14—C15—C10	0.2 (2)
O2—C7—C8—O1	7.51 (19)	C11—C10—C15—C14	0.4 (2)
C6—C7—C8—O1	−173.62 (11)	C9—C10—C15—C14	−176.08 (13)
C8—O1—C9—O3	−14.3 (2)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···F1i	0.95	2.55	3.1334 (17)	120
C8—H8B···O3ii	0.99	2.43	3.3517 (19)	154
C11—H11A···O4iii	0.95	2.53	3.380 (2)	150
C1—H1A···Cg2iv	0.95	2.59	3.3693 (17)	139
C8—H8A···Cg1v	0.99	2.83	3.5309 (19)	128

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯F1i	0.95	2.55	3.1334 (17)	120
C8—H8B⋯O3ii	0.99	2.43	3.3517 (19)	154
C11—H11A⋯O4iii	0.95	2.53	3.380 (2)	150
C1—H1A⋯Cg2iv	0.95	2.59	3.3693 (17)	139
C8—H8A⋯Cg1v	0.99	2.83	3.5309 (19)	128

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