| Figure 1 The crystal structure of the title compound, showing a hydrogen-bonded dimer with labelling and displacement ellipsoids drawn at the 50% probability level. Hydrogen bonding is indicated by dashed lines. [Symmetry code: (i) −x, 2 − y, 1 − z.] |
Experimental
Compound (I
) was commercially available from Acros Organics (Loughborough, England). It was recrystallized from an aqueous solution.
Data collection
SMART 6000 CCD area-detector diffractometer ω scans Absorption correction: none 9290 measured reflections 2036 independent reflections 1773 reflections with I > 2σ(I) Rint = 0.067 θmax = 30.0° h = −5 → 5 k = −8 → 8 l = −42 → 42
|
F—C3 | 1.3595 (17) | O1—C7 | 1.3076 (18) | O2—C7 | 1.2354 (18) | C1—C6 | 1.389 (2) | C1—C2 | 1.395 (2) | C1—C7 | 1.481 (2) | C2—C3 | 1.379 (2) | C3—C4 | 1.389 (2) | C4—C5 | 1.396 (2) | C4—C8 | 1.505 (2) | C5—C6 | 1.393 (2) | | C6—C1—C2 | 120.18 (13) | C3—C2—C1 | 117.86 (14) | F—C3—C2 | 117.88 (14) | F—C3—C4 | 117.96 (13) | C2—C3—C4 | 124.15 (14) | C3—C4—C5 | 116.56 (14) | C3—C4—C8 | 121.47 (14) | C5—C4—C8 | 121.97 (15) | C6—C5—C4 | 121.15 (14) | C1—C6—C5 | 120.10 (14) | | |
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | O1—H01⋯O2i | 0.92 (4) | 1.70 (4) | 2.6117 (17) | 176 (3) | Symmetry code: (i) -x,2-y,1-z. | |
All H atoms were located in a difference map and were refined freely.
Data collection: SMART (Bruker, 2001
); cell refinement: SMART; data reduction: SAINT (Bruker, 2001
); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997
); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997
); molecular graphics: SHELXTL (Bruker, 2001
); software used to prepare material for publication: SHELXTL.
Supporting information
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
3-fluoro-4-methylbenzoic acid
top Crystal data top C8H7FO2 | F(000) = 320 |
Mr = 154.14 | Dx = 1.469 Mg m−3 |
Monoclinic, P21/c | Melting point = 442–444 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 3.8132 (5) Å | Cell parameters from 979 reflections |
b = 6.0226 (8) Å | θ = 10.3–26.0° |
c = 30.378 (4) Å | µ = 0.12 mm−1 |
β = 92.50 (2)° | T = 120 K |
V = 696.98 (16) Å3 | Prism, colourless |
Z = 4 | 0.55 × 0.19 × 0.16 mm |
Data collection top SMART 6000 CCD area-detector diffractometer | 1773 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.067 |
Graphite monochromator | θmax = 30.0°, θmin = 1.3° |
Detector resolution: 8 pixels mm-1 | h = −5→5 |
ω scans | k = −8→8 |
9290 measured reflections | l = −42→42 |
2036 independent reflections | |
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)] = 0.054 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.157 | All H-atom parameters refined |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0713P)2 + 0.4137P] where P = (Fo2 + 2Fc2)/3 |
2036 reflections | (Δ/σ)max < 0.001 |
128 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Special details top Experimental. The data collection nominally covered full sphere of reciprocal space, by a combination of 4 sets of ω scans; each set at different φ and/or 2θ angles and each scan (10 sec exposure) covering 0.3° in ω. Crystal to detector distance 4.85 cm. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
F | 0.1213 (3) | 0.71029 (19) | 0.29337 (3) | 0.0340 (3) | |
O1 | 0.2296 (4) | 0.7513 (2) | 0.48864 (4) | 0.0310 (3) | |
H01 | 0.167 (9) | 0.843 (6) | 0.5110 (11) | 0.069 (9)* | |
O2 | −0.0547 (3) | 0.9999 (2) | 0.44542 (4) | 0.0273 (3) | |
C1 | 0.2068 (4) | 0.6875 (2) | 0.41215 (5) | 0.0194 (3) | |
C2 | 0.1227 (4) | 0.7663 (3) | 0.36981 (5) | 0.0211 (3) | |
H2 | −0.001 (6) | 0.911 (4) | 0.3651 (7) | 0.028 (5)* | |
C3 | 0.2043 (4) | 0.6340 (3) | 0.33464 (5) | 0.0227 (3) | |
C4 | 0.3647 (4) | 0.4276 (3) | 0.33872 (5) | 0.0222 (3) | |
C5 | 0.4442 (4) | 0.3533 (3) | 0.38153 (5) | 0.0232 (3) | |
H5 | 0.565 (6) | 0.209 (4) | 0.3840 (7) | 0.026 (5)* | |
C6 | 0.3668 (4) | 0.4818 (3) | 0.41798 (5) | 0.0220 (3) | |
H6 | 0.423 (6) | 0.428 (4) | 0.4486 (7) | 0.030 (5)* | |
C7 | 0.1160 (4) | 0.8265 (2) | 0.45024 (5) | 0.0206 (3) | |
C8 | 0.4497 (5) | 0.2923 (3) | 0.29891 (6) | 0.0305 (4) | |
H81 | 0.597 (7) | 0.368 (5) | 0.2804 (9) | 0.049 (7)* | |
H82 | 0.592 (8) | 0.165 (5) | 0.3067 (9) | 0.052 (8)* | |
H83 | 0.247 (8) | 0.252 (5) | 0.2817 (10) | 0.049 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F | 0.0460 (6) | 0.0376 (6) | 0.0181 (5) | 0.0058 (5) | −0.0011 (4) | 0.0025 (4) |
O1 | 0.0440 (7) | 0.0308 (6) | 0.0179 (5) | 0.0139 (5) | −0.0005 (5) | −0.0008 (4) |
O2 | 0.0357 (6) | 0.0240 (6) | 0.0219 (5) | 0.0085 (5) | 0.0003 (4) | −0.0002 (4) |
C1 | 0.0196 (6) | 0.0198 (6) | 0.0191 (6) | 0.0008 (5) | 0.0015 (5) | −0.0002 (5) |
C2 | 0.0216 (6) | 0.0207 (7) | 0.0211 (7) | 0.0017 (5) | 0.0008 (5) | 0.0007 (5) |
C3 | 0.0240 (7) | 0.0265 (7) | 0.0176 (6) | −0.0024 (6) | 0.0002 (5) | 0.0007 (5) |
C4 | 0.0177 (6) | 0.0258 (7) | 0.0231 (7) | −0.0013 (5) | 0.0025 (5) | −0.0048 (5) |
C5 | 0.0214 (6) | 0.0216 (7) | 0.0267 (7) | 0.0023 (5) | 0.0014 (5) | −0.0017 (5) |
C6 | 0.0220 (6) | 0.0222 (7) | 0.0218 (7) | 0.0018 (5) | 0.0003 (5) | 0.0002 (5) |
C7 | 0.0223 (6) | 0.0209 (7) | 0.0186 (6) | 0.0011 (5) | 0.0013 (5) | 0.0003 (5) |
C8 | 0.0293 (8) | 0.0356 (9) | 0.0268 (8) | 0.0023 (7) | 0.0031 (6) | −0.0099 (7) |
Geometric parameters (Å, º) top F—C3 | 1.3595 (17) | C3—C4 | 1.389 (2) |
O1—C7 | 1.3076 (18) | C4—C5 | 1.396 (2) |
O1—H01 | 0.92 (4) | C4—C8 | 1.505 (2) |
O2—C7 | 1.2354 (18) | C5—C6 | 1.393 (2) |
C1—C6 | 1.389 (2) | C5—H5 | 0.98 (2) |
C1—C2 | 1.395 (2) | C6—H6 | 1.00 (2) |
C1—C7 | 1.481 (2) | C8—H81 | 0.93 (3) |
C2—C3 | 1.379 (2) | C8—H82 | 0.96 (3) |
C2—H2 | 1.00 (2) | C8—H83 | 0.95 (3) |
| | | |
C7—O1—H01 | 111 (2) | C6—C5—H5 | 123.0 (13) |
C6—C1—C2 | 120.18 (13) | C4—C5—H5 | 115.8 (13) |
C6—C1—C7 | 121.39 (13) | C1—C6—C5 | 120.10 (14) |
C2—C1—C7 | 118.42 (13) | C1—C6—H6 | 118.9 (14) |
C3—C2—C1 | 117.86 (14) | C5—C6—H6 | 121.0 (14) |
C3—C2—H2 | 120.9 (13) | O2—C7—O1 | 123.44 (14) |
C1—C2—H2 | 121.2 (13) | O2—C7—C1 | 121.65 (13) |
F—C3—C2 | 117.88 (14) | O1—C7—C1 | 114.91 (13) |
F—C3—C4 | 117.96 (13) | C4—C8—H81 | 112.2 (18) |
C2—C3—C4 | 124.15 (14) | C4—C8—H82 | 111.8 (17) |
C3—C4—C5 | 116.56 (14) | H81—C8—H82 | 101 (2) |
C3—C4—C8 | 121.47 (14) | C4—C8—H83 | 112.7 (18) |
C5—C4—C8 | 121.97 (15) | H81—C8—H83 | 107 (2) |
C6—C5—C4 | 121.15 (14) | H82—C8—H83 | 112 (2) |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
O1—H01···O2i | 0.92 (4) | 1.70 (4) | 2.6117 (17) | 176 (3) |
Symmetry code: (i) −x, −y+2, −z+1. |
References
Antonioli, G. C. (2004). PhD thesis, University of Durham, England. Google Scholar
Bruker (2001). SMART (Version 5.625), SAINT (Version 6.02A) and SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Takwale, M. G. & Pant, L. M. (1971). Acta Cryst. B27, 1152–1158. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
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