(3,4-Dimeth­oxy­phen­yl)(4-fluoro­phen­yl)methanone

Lv, Q.; Wang, J.

doi:10.1107/S1600536810021008

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1585

doi:10.1107/S1600536810021008

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(3,4-Dimethoxyphenyl)(4-fluorophenyl)methanone

Quanjian Lv ^a ^* and Jianling Wang ^a

^aDepartment of Quality Detection and Management, Zhengzhou College of Animal Husbandry Engineering, Zhengzhou 450011, People's Republic of China
^*Correspondence e-mail: jyzhang2004@126.com

(Received 22 May 2010; accepted 2 June 2010; online 5 June 2010)

In the title compound, C₁₅H₁₃FO₃, the dihedral angle between the two aromatic rings is 52.78 (8)°. In the crystal, intermolecular C—H⋯O hydrogen bonds link molecules 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_r = 260.25
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.056
wR(F²) = 0.173
S = 1.00
2227 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Benzophenone derivatives are an important class of compounds having a broad spectrum of applications in the chemical and biochemical fields (Riechers et al., 1996; Khanum et al., 2009), and are widely used as UV-screens to protect industrial products from light induced damage (Schlecht et al., 2008). In order to develop new applications for benzophenone and its derivatives, structural modifications of benzophenone have been extensively investigated. As a contribution to this field, we report here the crystal structure of the title compound.

The molecular structure of title compound is shown in Fig. 1. The dihedral angle formed by the benzene rings 52.78 (8)°. In the crystal packing (Fig. 2), intermolecular C—H···O hydrogen bonds (Table 1) link molecules into chains running parallel to the c axis.

Related literature top

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

Experimental top

To a solution of 1,2-dimethoxybenzene (138 g, 1.00 mol) in dichloromethane (2.00 l), AlCl₃ (199 g, 1.50 mol) was added. Then 4-fluorobenzoyl chloride (158 g, 2.00 mol) was added. The mixture was stirred at room temperature for 2 h, followed by filtration and purification by crystallization from ethyl acetate, giving the title compound as a colourless crystalline solid.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the compound, with atom labels and 50% probability displacement ellipsoids. Hydrogen atoms are omitted.
	Fig. 2. Crystal packing of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

(3,4-Dimethoxyphenyl)(4-fluorophenyl)methanone top

Crystal data top

C₁₅H₁₃FO₃	F(000) = 544
M_r = 260.25	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0915P)²] where P = (F_o² + 2F_c²)/3
2227 reflections	(Δ/σ)_max < 0.001
174 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₅H₁₃FO₃	V = 1273.6 (2) Å³
M_r = 260.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.8926 (9) Å	µ = 0.10 mm⁻¹
b = 11.3632 (11) Å	T = 298 K
c = 10.8369 (10) Å	0.48 × 0.38 × 0.15 mm
β = 108.285 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2227 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1391 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.985	R_int = 0.083
6183 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 1.00	Δρ_max = 0.20 e Å⁻³
2227 reflections	Δρ_min = −0.32 e Å⁻³
174 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃FO₃
M_r	260.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.8926 (9), 11.3632 (11), 10.8369 (10)
β (°)	108.285 (1)
V (Å³)	1273.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.48 × 0.38 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.952, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	6183, 2227, 1391
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.173, 1.00
No. of reflections	2227
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.32

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1ⁱ	0.93	2.58	3.343 (3)	139.2

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

We gratefully acknowledge financial support from the National Natural Science Foundation of China (No. 20572103).

References

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