Related literature {#sec1}
==================

For related structures and background to phenacyl benzoates, see: Fun *et al.* (2011**a*[@bb3],b* [@bb4]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[@bb2]).

Experimental {#sec2}
============

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~16~H~13~FO~4~*M* *~r~* = 288.26Monoclinic,*a* = 9.3523 (2) Å*b* = 10.1949 (2) Å*c* = 15.6465 (4) Åβ = 118.842 (2)°*V* = 1306.77 (5) Å^3^*Z* = 4Mo *K*α radiationμ = 0.11 mm^−1^*T* = 100 K0.29 × 0.25 × 0.15 mm

### Data collection {#sec2.1.2}

Bruker SMART APEXII CCD diffractometerAbsorption correction: multi-scan (*SADABS*; Bruker, 2009[@bb1]) *T* ~min~ = 0.967, *T* ~max~ = 0.98418005 measured reflections4669 independent reflections3194 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.061

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.055*wR*(*F* ^2^) = 0.151*S* = 1.034669 reflections191 parametersH-atom parameters constrainedΔρ~max~ = 0.53 e Å^−3^Δρ~min~ = −0.29 e Å^−3^

 {#d5e505}

Data collection: *APEX2* (Bruker, 2009[@bb1]); cell refinement: *SAINT* (Bruker, 2009[@bb1]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXTL* (Sheldrick, 2008[@bb5]); program(s) used to refine structure: *SHELXTL*; molecular graphics: *SHELXTL*; software used to prepare material for publication: *SHELXTL* and *PLATON* (Spek, 2009[@bb6]).

Supplementary Material
======================

Crystal structure: contains datablock(s) global, I. DOI: [10.1107/S1600536811049233/hb6504sup1.cif](http://dx.doi.org/10.1107/S1600536811049233/hb6504sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536811049233/hb6504Isup2.hkl](http://dx.doi.org/10.1107/S1600536811049233/hb6504Isup2.hkl)

Supplementary material file. DOI: [10.1107/S1600536811049233/hb6504Isup3.cml](http://dx.doi.org/10.1107/S1600536811049233/hb6504Isup3.cml)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?hb6504&file=hb6504sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?hb6504sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?hb6504&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [HB6504](http://scripts.iucr.org/cgi-bin/sendsup?hb6504)).

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PFIZIK/811160). AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young scientist award. SMN thanks the Department of Information Technology, New Delhi, India, for financial support.

Comment
=======

As part of our ongoing studies of phenacyl benzoates (Fun *et al.*, 2011*a*,*b*), we now report the synthesis and structure of the title compound.

In the title compound (Fig. 1), the dihedral angle formed between the fluoro-substituted (C1--C6) and the methoxy-substituted (C10--C15) benzene rings is 84.28 (8)°. Bond lengths and angles are within the normal ranges and are comparable to the related structures (Fun *et al.*, 2011**a*,b*).

In the crystal (Fig. 2), C4---H4A···F1, C8---H8B···O3 and C11---H11A···O4 hydrogen bonds (Table 1) link the molecules together to form a three-dimensional network. The crystal structure is further stabilized by C--H···π interactions (Table 1) involving the fluoro-substituted (*Cg*1) and the methoxy-substituted (*Cg*2) benzene rings.

Experimental {#experimental}
============

A mixture of 4-methoxybenzoic acid (1.0 g, 0.0065 mol), potassium carbonate (0.99 g, 0.0072 mol) and 2-bromo-1-(4-fluorophenyl)ethanone (1.41 g, 0.0065 mol) in dimethylformamide (10 ml) was stirred at room temperature for 2 h. On cooling, colourless needle-shaped crystals of 2-(4-fluorophenyl)-2-oxoethyl 4-methoxybenzoate began to separate. It was collected by filtration and recrystallized from ethanol to yield yellow blocks of (I). Yield: 1.72 g, 91.0%. *M.p*: 387--388 K.

Refinement {#refinement}
==========

All H atoms were positioned geometrically and refined with a riding model with *U*~iso~(H) = 1.2 or 1.5 *U*~eq~(C) \[C--H = 0.95 or 0.99 Å\]. A rotating group model was applied to the methyl group.

Figures
=======

![The molecular structure of the title compound, showing 50% probability displacement ellipsoids.](e-67-o3456-fig1){#Fap1}

![The crystal packing of the title compound, viewed along the b axis, showing the three-dimensional network. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.](e-67-o3456-fig2){#Fap2}

Crystal data {#tablewrapcrystaldatalong}
============

  ------------------------- ---------------------------------------
  C~16~H~13~FO~4~           *F*(000) = 600
  *M~r~* = 288.26           *D*~x~ = 1.465 Mg m^−3^
  Monoclinic, *P*2~1~/*c*   Mo *K*α 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) Å^3^    0.29 × 0.25 × 0.15 mm
  *Z* = 4                   
  ------------------------- ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  ------------------------------------------------------------ --------------------------------------
  Bruker SMART APEXII CCD diffractometer                       4669 independent reflections
  Radiation source: fine-focus sealed tube                     3194 reflections with *I* \> 2σ(*I*)
  graphite                                                     *R*~int~ = 0.061
  φ and ω scans                                                θ~max~ = 32.4°, θ~min~ = 2.5°
  Absorption correction: multi-scan (*SADABS*; Bruker, 2009)   *h* = −14→14
  *T*~min~ = 0.967, *T*~max~ = 0.984                           *k* = −15→10
  18005 measured reflections                                   *l* = −23→23
  ------------------------------------------------------------ --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- -------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.055   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.151                  H-atom parameters constrained
  *S* = 1.03                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0735*P*)^2^ + 0.1795*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  4669 reflections                      (Δ/σ)~max~ \< 0.001
  191 parameters                        Δρ~max~ = 0.53 e Å^−3^
  0 restraints                          Δρ~min~ = −0.29 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  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 *F*^2^ against ALL reflections. The weighted *R*-factor *wR* and goodness of fit *S* are based on *F*^2^, conventional *R*-factors *R* are based on *F*, with *F* set to zero for negative *F*^2^. The threshold expression of *F*^2^ \> σ(*F*^2^) is used only for calculating *R*-factors(gt) *etc*. and is not relevant to the choice of reflections for refinement. *R*-factors based on *F*^2^ 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 (Å^2^) {#tablewrapcoords}
==================================================================================================

  ------ -------------- -------------- -------------- -------------------- --
         *x*            *y*            *z*            *U*~iso~\*/*U*~eq~   
  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\*              
  ------ -------------- -------------- -------------- -------------------- --

Atomic displacement parameters (Å^2^) {#tablewrapadps}
=====================================

  ----- ------------ ------------ ------------ ------------- ------------ -------------
        *U*^11^      *U*^22^      *U*^33^      *U*^12^       *U*^13^      *U*^23^
  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)
  ----- ------------ ------------ ------------ ------------- ------------ -------------

Geometric parameters (Å, °) {#tablewrapgeomlong}
===========================

  ------------------- -------------- ----------------------- --------------
  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)                              
  ------------------- -------------- ----------------------- --------------

Hydrogen-bond geometry (Å, °) {#tablewraphbondslong}
=============================

  -------------------------------------------------------------------------------
  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···F1^i^       0.95      2.55      3.1334 (17)   120
  C8---H8B···O3^ii^      0.99      2.43      3.3517 (19)   154
  C11---H11A···O4^iii^   0.95      2.53      3.380 (2)     150
  C1---H1A···Cg2^iv^     0.95      2.59      3.3693 (17)   139
  C8---H8A···Cg1^v^      0.99      2.83      3.5309 (19)   128
  ---------------------- --------- --------- ------------- ---------------

Symmetry codes: (i) −*x*+1, −*y*, −*z*+2; (ii) −*x*+2, −*y*+1, −*z*+2; (iii) −*x*+2, *y*−1/2, −*z*+3/2; (iv) −*x*+1, *y*−1/2, −*z*+3/2; (v) −*x*+1, −*y*+1, −*z*+2.

###### Hydrogen-bond geometry (Å, °)

*Cg*1 and *Cg*2 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---H4*A*⋯F1^i^       0.95      2.55    3.1334 (17)   120
  C8---H8*B*⋯O3^ii^      0.99      2.43    3.3517 (19)   154
  C11---H11*A*⋯O4^iii^   0.95      2.53    3.380 (2)     150
  C1---H1*A*⋯*Cg*2^iv^   0.95      2.59    3.3693 (17)   139
  C8---H8*A*⋯*Cg*1^v^    0.99      2.83    3.5309 (19)   128

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

[^1]: Thomson Reuters ResearcherID: A-3561-2009.

[^2]: Thomson Reuters ResearcherID: C-7581-2009.
