(3,4-Dimeth-oxy-phen-yl)(4-fluoro-phen-yl)methanone.

In the title compound, C(15)H(13)FO(3), the dihedral angle between the two aromatic rings is 52.78 (8)°. In the crystal, inter-molecular C-H⋯O hydrogen bonds link mol-ecules into chains running parallel to the c axis.

Related literature

For applications of benzophenone and its derivatives, see: Riechers et al. (1996 ▶); Khanum et al. (2009 ▶); Schlecht et al. (2008 ▶).

Experimental

Crystal data

C15H13FO3

M = 260.25

Monoclinic,

a = 10.8926 (9) Å

b = 11.3632 (11) Å

c = 10.8369 (10) Å

β = 108.285 (1)°

V = 1273.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.48 × 0.38 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.952, T max = 0.985

6183 measured reflections

2227 independent reflections

1391 reflections with I > 2σ(I)

R int = 0.083

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.173

S = 1.00

2227 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021008/rz2456sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021008/rz2456Isup2.hkl

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

C15H13FO3	F(000) = 544
Mr = 260.25	Dx = 1.357 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1872 reflections
a = 10.8926 (9) Å	θ = 2.7–26.1°
b = 11.3632 (11) Å	µ = 0.10 mm−1
c = 10.8369 (10) Å	T = 298 K
β = 108.285 (1)°	Needle, colourless
V = 1273.6 (2) Å3	0.48 × 0.38 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2227 independent reflections
Radiation source: fine-focus sealed tube	1391 reflections with I > 2σ(I)
graphite	Rint = 0.083
phi and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→12
Tmin = 0.952, Tmax = 0.985	k = −13→13
6183 measured reflections	l = −12→12

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0915P)2] where P = (Fo2 + 2Fc2)/3
2227 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.20 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
F1	0.13858 (16)	0.52452 (18)	−0.33034 (17)	0.0864 (7)
O1	0.46324 (18)	0.62209 (18)	0.24672 (19)	0.0638 (6)
O2	0.88706 (15)	0.85244 (17)	0.40525 (17)	0.0555 (6)
O3	0.86314 (15)	1.01546 (15)	0.23481 (17)	0.0512 (5)
C1	0.4782 (2)	0.6672 (2)	0.1495 (3)	0.0433 (6)
C2	0.5825 (2)	0.7552 (2)	0.1622 (2)	0.0384 (6)
C3	0.6868 (2)	0.7580 (2)	0.2777 (2)	0.0420 (6)
H3	0.6928	0.7015	0.3414	0.050*
C4	0.7801 (2)	0.8432 (2)	0.2976 (2)	0.0405 (6)
C5	0.7682 (2)	0.9316 (2)	0.2037 (2)	0.0392 (6)
C6	0.6666 (2)	0.9291 (2)	0.0898 (2)	0.0416 (6)
H6	0.6597	0.9865	0.0269	0.050*
C7	0.5739 (2)	0.8405 (2)	0.0688 (2)	0.0399 (6)
H7	0.5057	0.8387	−0.0086	0.048*
C8	0.8996 (3)	0.7711 (3)	0.5078 (3)	0.0682 (9)
H8A	0.8272	0.7790	0.5397	0.102*
H8B	0.9782	0.7867	0.5768	0.102*
H8C	0.9020	0.6925	0.4761	0.102*
C9	0.8510 (3)	1.1108 (3)	0.1468 (3)	0.0664 (9)
H9A	0.8506	1.0811	0.0637	0.100*
H9B	0.9225	1.1637	0.1798	0.100*
H9C	0.7715	1.1519	0.1374	0.100*
C10	0.3889 (2)	0.6332 (2)	0.0193 (2)	0.0396 (6)
C11	0.2630 (2)	0.6010 (2)	0.0084 (3)	0.0475 (7)
H11	0.2355	0.6042	0.0813	0.057*
C12	0.1782 (3)	0.5644 (2)	−0.1084 (3)	0.0545 (7)
H12	0.0938	0.5431	−0.1154	0.065*
C13	0.2215 (3)	0.5604 (3)	−0.2141 (3)	0.0554 (8)
C14	0.3456 (3)	0.5881 (3)	−0.2083 (3)	0.0559 (8)
H14	0.3728	0.5816	−0.2812	0.067*
C15	0.4290 (2)	0.6260 (2)	−0.0911 (3)	0.0462 (7)
H15	0.5131	0.6470	−0.0854	0.055*

	U11	U22	U33	U12	U13	U23
F1	0.0788 (12)	0.1100 (15)	0.0628 (12)	−0.0321 (12)	0.0113 (9)	−0.0168 (10)
O1	0.0677 (13)	0.0799 (14)	0.0502 (12)	−0.0215 (11)	0.0274 (10)	0.0033 (10)
O2	0.0450 (11)	0.0706 (13)	0.0473 (11)	−0.0113 (9)	0.0094 (9)	0.0127 (9)
O3	0.0463 (11)	0.0513 (11)	0.0573 (12)	−0.0076 (9)	0.0183 (8)	0.0060 (9)
C1	0.0400 (14)	0.0476 (15)	0.0491 (16)	0.0021 (12)	0.0239 (12)	0.0029 (12)
C2	0.0338 (13)	0.0456 (14)	0.0422 (14)	0.0041 (11)	0.0210 (10)	−0.0028 (11)
C3	0.0398 (14)	0.0480 (15)	0.0446 (15)	0.0002 (12)	0.0223 (11)	0.0055 (12)
C4	0.0317 (13)	0.0504 (15)	0.0427 (15)	0.0043 (12)	0.0165 (11)	0.0016 (12)
C5	0.0366 (13)	0.0412 (14)	0.0457 (15)	0.0032 (12)	0.0215 (11)	−0.0022 (11)
C6	0.0440 (14)	0.0427 (14)	0.0433 (14)	0.0050 (12)	0.0210 (11)	0.0036 (11)
C7	0.0353 (13)	0.0463 (14)	0.0402 (14)	0.0060 (12)	0.0148 (10)	−0.0010 (11)
C8	0.0643 (19)	0.080 (2)	0.0492 (17)	−0.0084 (17)	0.0021 (14)	0.0185 (16)
C9	0.076 (2)	0.0543 (17)	0.069 (2)	−0.0170 (16)	0.0224 (16)	0.0105 (15)
C10	0.0358 (13)	0.0402 (14)	0.0490 (16)	−0.0007 (11)	0.0225 (11)	0.0006 (11)
C11	0.0426 (14)	0.0522 (16)	0.0568 (17)	−0.0010 (13)	0.0286 (12)	0.0019 (13)
C12	0.0389 (14)	0.0595 (18)	0.0688 (19)	−0.0084 (14)	0.0223 (13)	−0.0028 (15)
C13	0.0566 (17)	0.0554 (18)	0.0515 (17)	−0.0119 (15)	0.0132 (13)	−0.0072 (14)
C14	0.0630 (18)	0.0610 (18)	0.0541 (18)	−0.0105 (15)	0.0332 (14)	−0.0102 (14)
C15	0.0396 (14)	0.0513 (15)	0.0560 (17)	−0.0068 (13)	0.0267 (12)	−0.0057 (13)

F1—C13	1.362 (3)	C8—H8A	0.9600
O1—C1	1.227 (3)	C8—H8B	0.9600
O2—C4	1.370 (3)	C8—H8C	0.9600
O2—C8	1.419 (3)	C9—H9A	0.9600
O3—C5	1.368 (3)	C9—H9B	0.9600
O3—C9	1.422 (3)	C9—H9C	0.9600
C1—C2	1.488 (3)	C10—C11	1.388 (3)
C1—C10	1.493 (3)	C10—C15	1.399 (3)
C2—C7	1.383 (3)	C11—C12	1.377 (4)
C2—C3	1.402 (3)	C11—H11	0.9300
C3—C4	1.370 (3)	C12—C13	1.370 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.407 (4)	C13—C14	1.370 (4)
C5—C6	1.376 (3)	C14—C15	1.378 (4)
C6—C7	1.393 (3)	C14—H14	0.9300
C6—H6	0.9300	C15—H15	0.9300
C7—H7	0.9300
C4—O2—C8	117.6 (2)	H8A—C8—H8C	109.5
C5—O3—C9	117.5 (2)	H8B—C8—H8C	109.5
O1—C1—C2	120.3 (2)	O3—C9—H9A	109.5
O1—C1—C10	118.7 (2)	O3—C9—H9B	109.5
C2—C1—C10	120.9 (2)	H9A—C9—H9B	109.5
C7—C2—C3	119.2 (2)	O3—C9—H9C	109.5
C7—C2—C1	121.9 (2)	H9A—C9—H9C	109.5
C3—C2—C1	118.6 (2)	H9B—C9—H9C	109.5
C4—C3—C2	120.6 (2)	C11—C10—C15	118.5 (2)
C4—C3—H3	119.7	C11—C10—C1	118.8 (2)
C2—C3—H3	119.7	C15—C10—C1	122.6 (2)
C3—C4—O2	125.4 (2)	C12—C11—C10	121.2 (2)
C3—C4—C5	119.7 (2)	C12—C11—H11	119.4
O2—C4—C5	114.9 (2)	C10—C11—H11	119.4
O3—C5—C6	124.7 (2)	C13—C12—C11	118.1 (2)
O3—C5—C4	115.4 (2)	C13—C12—H12	121.0
C6—C5—C4	119.9 (2)	C11—C12—H12	121.0
C5—C6—C7	120.0 (2)	F1—C13—C12	118.7 (2)
C5—C6—H6	120.0	F1—C13—C14	118.0 (3)
C7—C6—H6	120.0	C12—C13—C14	123.2 (3)
C2—C7—C6	120.5 (2)	C13—C14—C15	118.0 (3)
C2—C7—H7	119.8	C13—C14—H14	121.0
C6—C7—H7	119.8	C15—C14—H14	121.0
O2—C8—H8A	109.5	C14—C15—C10	120.9 (2)
O2—C8—H8B	109.5	C14—C15—H15	119.5
H8A—C8—H8B	109.5	C10—C15—H15	119.5
O2—C8—H8C	109.5
O1—C1—C2—C7	−153.7 (3)	C3—C2—C7—C6	−0.9 (3)
C10—C1—C2—C7	25.5 (3)	C1—C2—C7—C6	173.2 (2)
O1—C1—C2—C3	20.4 (3)	C5—C6—C7—C2	0.5 (3)
C10—C1—C2—C3	−160.4 (2)	O1—C1—C10—C11	30.4 (3)
C7—C2—C3—C4	−0.7 (4)	C2—C1—C10—C11	−148.8 (2)
C1—C2—C3—C4	−175.1 (2)	O1—C1—C10—C15	−145.9 (3)
C2—C3—C4—O2	−178.5 (2)	C2—C1—C10—C15	34.9 (3)
C2—C3—C4—C5	2.7 (4)	C15—C10—C11—C12	−1.0 (4)
C8—O2—C4—C3	−3.3 (4)	C1—C10—C11—C12	−177.4 (2)
C8—O2—C4—C5	175.4 (2)	C10—C11—C12—C13	0.2 (4)
C9—O3—C5—C6	4.3 (3)	C11—C12—C13—F1	−179.9 (2)
C9—O3—C5—C4	−176.1 (2)	C11—C12—C13—C14	1.6 (5)
C3—C4—C5—O3	177.30 (19)	F1—C13—C14—C15	179.1 (2)
O2—C4—C5—O3	−1.6 (3)	C12—C13—C14—C15	−2.4 (5)
C3—C4—C5—C6	−3.1 (4)	C13—C14—C15—C10	1.5 (4)
O2—C4—C5—C6	178.1 (2)	C11—C10—C15—C14	0.2 (4)
O3—C5—C6—C7	−179.0 (2)	C1—C10—C15—C14	176.5 (2)
C4—C5—C6—C7	1.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1i	0.93	2.58	3.343 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.93	2.58	3.343 (3)	139

Symmetry code: (i) .