Literature DB >> 21581248

2-(2-Fluoro-benzoyl-meth-yl)benzoic acid.

Muhammad Tahir Hussain, Tariq Mahmood Babar, Ghulam Qadeer, Nasim Hasan Rama, Ales Ruzicka.

Abstract

In the title compound, C(15)H(11)FO(3), the aromatic rings are oriented at a dihedral angle of 69.26 (3)°. In the crystal structure, inversion dimers arise from pairs of inter-molecular O-H⋯O hydrogen bonds, and C-H⋯O hydrogen bonds further consolidate the packing. There are also C-H⋯π contacts between the benzoic acid and 2-fluoro-benzene rings.

Entities: Chemical Disease Gene

Year: 2008 PMID： 21581248 PMCID： PMC2960007 DOI： 10.1107/S160053680803540X

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the biological activity of isocoumarin and 3,4-dihydroisocoumarin derivatives, see: Hill (1986 ▶); Napolitano (1997 ▶); Oikawa et al. (1997 ▶); Kongsaeree et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H11FO3 M = 258.24 Monoclinic, a = 8.3011 (6) Å b = 15.3232 (8) Å c = 9.9078 (10) Å β = 96.942 (8)° V = 1251.02 (17) Å3 Z = 4 Mo Kα radiation μ = 0.10 mm−1 T = 150 (1) K 0.52 × 0.38 × 0.30 mm

Data collection

Bruker–Nonius Kappa CCD area-detector diffractometer Absorption correction: Gaussian (Coppens, 1970 ▶) T min = 0.962, T max = 0.975 8420 measured reflections 2782 independent reflections 2117 reflections with I > 2σ(I) R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.136 S = 1.12 2782 reflections 172 parameters H-atom parameters constrained Δρmax = 0.23 e Å−3 Δρmin = −0.29 e Å−3 Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: COLLECT and DENZO (Otwinowski & Minor, 1997 ▶); data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803540X/hk2566sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680803540X/hk2566Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₁FO₃	F₀₀₀ = 536
M_r = 258.24	D_x = 1.371 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 404(1) K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 8.3011 (6) Å	Cell parameters from 8503 reflections
b = 15.3232 (8) Å	θ = 1–27.5º
c = 9.9078 (10) Å	µ = 0.11 mm⁻¹
β = 96.942 (8)º	T = 150 (1) K
V = 1251.02 (17) Å³	Block, colorless
Z = 4	0.52 × 0.38 × 0.31 mm

Bruker–Nonius Kappa CCD area-detector diffractometer	2782 independent reflections
Radiation source: fine-focus sealed tube	2117 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.040
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5º
T = 150(1) K	θ_min = 2.5º
φ and ω scans	h = −9→10
Absorption correction: Gaussian(Coppens, 1970)	k = −18→19
T_min = 0.962, T_max = 0.975	l = −12→12
8420 measured reflections

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.136	w = 1/[σ²(F_o²) + (0.0382P)² + 0.8217P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
2782 reflections	Δρ_max = 0.23 e Å⁻³
172 parameters	Δρ_min = −0.29 e Å⁻³
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	U_iso*/U_eq
F1	0.15542 (18)	−0.18437 (8)	0.10130 (16)	0.0594 (4)
O1	0.3928 (2)	−0.00007 (12)	0.35571 (16)	0.0573 (5)
O2	0.61607 (19)	0.07728 (11)	0.40921 (15)	0.0504 (4)
H2	0.6161	0.0506	0.4809	0.061*
O3	0.0632 (2)	0.07181 (10)	0.1708 (2)	0.0626 (5)
C1	0.4909 (2)	0.05329 (13)	0.3244 (2)	0.0361 (4)
C2	0.4762 (2)	0.09750 (12)	0.1908 (2)	0.0326 (4)
C3	0.3662 (2)	0.06805 (12)	0.08185 (19)	0.0316 (4)
C4	0.3530 (3)	0.11624 (15)	−0.0370 (2)	0.0410 (5)
H4	0.2814	0.0979	−0.1111	0.049*
C5	0.4429 (3)	0.19136 (15)	−0.0483 (2)	0.0477 (6)
H5	0.4292	0.2236	−0.1284	0.057*
C6	0.5523 (3)	0.21865 (14)	0.0580 (2)	0.0468 (5)
H6	0.6140	0.2686	0.0499	0.056*
C7	0.5704 (3)	0.17144 (13)	0.1770 (2)	0.0397 (5)
H7	0.6464	0.1889	0.2485	0.048*
C8	0.2660 (2)	−0.01340 (13)	0.0886 (2)	0.0335 (4)
H8A	0.3338	−0.0593	0.1325	0.040*
H8B	0.2282	−0.0325	−0.0032	0.040*
C9	0.1223 (2)	0.00021 (12)	0.1651 (2)	0.0344 (4)
C10	0.0483 (2)	−0.07466 (12)	0.2322 (2)	0.0330 (4)
C11	0.0665 (2)	−0.16193 (13)	0.2005 (2)	0.0395 (5)
C12	−0.0064 (3)	−0.22847 (15)	0.2627 (3)	0.0520 (6)
H12	0.0071	−0.2862	0.2371	0.062*
C13	−0.1001 (3)	−0.20839 (18)	0.3633 (3)	0.0599 (7)
H13	−0.1490	−0.2527	0.4079	0.072*
C14	−0.1213 (3)	−0.12269 (19)	0.3988 (3)	0.0603 (7)
H14	−0.1854	−0.1092	0.4667	0.072*
C15	−0.0491 (3)	−0.05654 (16)	0.3331 (2)	0.0469 (5)
H15	−0.0654	0.0011	0.3573	0.056*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0607 (9)	0.0356 (7)	0.0886 (11)	−0.0018 (6)	0.0356 (8)	−0.0117 (7)
O1	0.0577 (10)	0.0698 (12)	0.0414 (9)	−0.0320 (9)	−0.0064 (7)	0.0151 (8)
O2	0.0525 (9)	0.0544 (10)	0.0422 (8)	−0.0221 (8)	−0.0034 (7)	0.0060 (7)
O3	0.0532 (10)	0.0293 (8)	0.1121 (15)	0.0072 (7)	0.0381 (10)	0.0056 (9)
C1	0.0367 (10)	0.0344 (10)	0.0375 (10)	−0.0062 (8)	0.0057 (8)	−0.0028 (8)
C2	0.0350 (10)	0.0281 (9)	0.0369 (10)	0.0002 (7)	0.0126 (8)	−0.0010 (7)
C3	0.0277 (9)	0.0324 (10)	0.0365 (10)	0.0044 (7)	0.0108 (8)	0.0008 (8)
C4	0.0351 (10)	0.0487 (12)	0.0402 (11)	0.0050 (9)	0.0086 (8)	0.0075 (9)
C5	0.0467 (12)	0.0463 (12)	0.0538 (13)	0.0066 (10)	0.0210 (11)	0.0179 (10)
C6	0.0495 (13)	0.0339 (11)	0.0614 (14)	−0.0047 (9)	0.0245 (11)	0.0058 (10)
C7	0.0410 (11)	0.0350 (11)	0.0455 (12)	−0.0050 (8)	0.0146 (9)	−0.0054 (9)
C8	0.0329 (10)	0.0320 (10)	0.0360 (10)	−0.0013 (8)	0.0050 (8)	−0.0019 (8)
C9	0.0309 (9)	0.0291 (10)	0.0432 (11)	0.0000 (8)	0.0046 (8)	−0.0005 (8)
C10	0.0293 (9)	0.0331 (10)	0.0363 (10)	−0.0006 (7)	0.0023 (7)	0.0001 (8)
C11	0.0325 (10)	0.0343 (10)	0.0522 (13)	0.0020 (8)	0.0068 (9)	0.0013 (9)
C12	0.0460 (12)	0.0328 (11)	0.0772 (17)	−0.0012 (9)	0.0074 (12)	0.0106 (11)
C13	0.0589 (15)	0.0561 (15)	0.0653 (16)	−0.0107 (12)	0.0103 (13)	0.0231 (13)
C14	0.0649 (17)	0.0703 (18)	0.0504 (14)	−0.0106 (13)	0.0257 (12)	0.0032 (12)
C15	0.0514 (13)	0.0455 (12)	0.0459 (12)	−0.0052 (10)	0.0142 (10)	−0.0059 (10)

F1—C11	1.343 (2)	C8—H8A	0.9700
O1—C1	1.220 (2)	C8—H8B	0.9700
O2—C1	1.308 (2)	C9—O3	1.206 (2)
O2—H2	0.8199	C9—C8	1.503 (3)
C2—C1	1.479 (3)	C9—C10	1.495 (3)
C2—C3	1.402 (3)	C10—C11	1.386 (3)
C2—C7	1.393 (3)	C10—C15	1.388 (3)
C3—C4	1.383 (3)	C11—C12	1.370 (3)
C3—C8	1.506 (3)	C12—C13	1.371 (4)
C4—C5	1.384 (3)	C12—H12	0.9299
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.370 (3)	C14—C13	1.376 (4)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9299	C15—C14	1.380 (3)
C7—C6	1.376 (3)	C15—H15	0.9300
C7—H7	0.9300

C1—O2—H2	109.5	C9—C8—H8B	109.1
O1—C1—O2	121.87 (19)	C3—C8—H8B	109.1
O1—C1—C2	123.30 (18)	H8A—C8—H8B	107.8
O2—C1—C2	114.80 (17)	O3—C9—C10	119.08 (18)
C7—C2—C3	120.47 (18)	O3—C9—C8	120.14 (18)
C7—C2—C1	118.31 (18)	C10—C9—C8	120.77 (16)
C3—C2—C1	121.18 (17)	C11—C10—C15	116.41 (19)
C4—C3—C2	117.49 (18)	C11—C10—C9	125.32 (18)
C4—C3—C8	119.50 (18)	C15—C10—C9	118.26 (18)
C2—C3—C8	123.00 (17)	F1—C11—C12	116.77 (19)
C3—C4—C5	121.6 (2)	F1—C11—C10	119.81 (18)
C3—C4—H4	119.2	C12—C11—C10	123.4 (2)
C5—C4—H4	119.2	C11—C12—C13	118.7 (2)
C6—C5—C4	120.4 (2)	C11—C12—H12	120.7
C6—C5—H5	119.7	C13—C12—H12	120.6
C4—C5—H5	119.9	C12—C13—C14	120.1 (2)
C5—C6—C7	119.4 (2)	C12—C13—H13	120.0
C5—C6—H6	120.4	C14—C13—H13	119.9
C7—C6—H6	120.2	C13—C14—C15	120.2 (2)
C6—C7—C2	120.5 (2)	C13—C14—H14	120.0
C6—C7—H7	119.7	C15—C14—H14	119.8
C2—C7—H7	119.8	C14—C15—C10	121.1 (2)
C9—C8—C3	112.56 (16)	C14—C15—H15	119.5
C9—C8—H8A	109.1	C10—C15—H15	119.4
C3—C8—H8A	109.1

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.80	2.621 (3)	175
C12—H12···O3ⁱⁱ	0.93	2.46	3.178 (3)	134
C4—H4···Cg2ⁱⁱⁱ	0.93	2.72	3.535 (3)	146
C13—H13···Cg1ⁱⁱ	0.93	3.06	3.868 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	1.80	2.621 (3)	175
C12—H12⋯O3ⁱⁱ	0.93	2.46	3.178 (3)	134
C4—H4⋯Cg2ⁱⁱⁱ	0.93	2.72	3.535 (3)	146
C13—H13⋯Cg1ⁱⁱ	0.93	3.06	3.868 (3)	146

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C2–C7 and C10–C15 rings, respectively.

3 in total

2-(2-Fluoro-benzoyl-meth-yl)benzoic acid.

Related literature

Experimental

Crystal data

Data collection

Refinement

1. A short history of SHELX.

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