Acta Cryst. (2009). E65, o802-o803 [ doi:10.1107/S1600536809008927 ]
In the title compound, C14H12FNO2, the fluorobenzene and methoxybenzene rings are inclined at 27.06 (7) and 23.86 (7)°, respectively, to the amide portion of the molecule and at 3.46 (9)° to one another. The methoxy substituent lies close to the methoxybenzene ring plane, with a maximum deviation of 0.152 (3) Å for the methyl C atom. In the crystal structure, intermolecular N-H
O hydrogen bonds link molecules into rows along a. Weak C-HO and C-HF interactions further stabilize the packing, forming corrugated sheets in the bc plane.
2-Fluorobenzoyl chloride (5.4 mmol) in CHCl3 was treated with 4-methoxyaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 3 h. Upon cooling, the reaction mixture was diluted with CHCl3 and washed consecutively with aq 1 M HCl and saturated aq NaHCO3. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Crystallization of the residue from CHCl3 afforded the title compound (81%) as white needles: Anal. calcd. for C14H12FNO2: C 68.56, H 4.93, N 5.71%; found: C 68.49, H 4.97, N 5.63%
The H atom bound to N1 was located in a difference map and refined isotropically. All other H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.95 Å, Uiso=1.2Ueq (C) for aromatic and 0.98 Å, Uiso = 1.5Ueq (C) for CH3 hydrogen atoms. In the absence of significant anomalous scattering effects, Friedel pairs were merged and a Flack parameter is not reported.
Data collection: APEX2 (Bruker 2006); cell refinement: APEX2 (Bruker 2006) and SAINT (Bruker 2006); data reduction: SAINT (Bruker 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2009).
![[Figure 1]](./si2159fig1thm.gif)
| Fig. 1. The structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level. |
![[Figure 2]](./si2159fig2thm.gif)
| Fig. 2. Crystal packing for (I) viewed down the b axis with hydrogen bonds drawn as dashed lines and H atoms not involved in hydrogen bonding omitted. |
| C14H12FNO2 | F(000) = 512 |
| Mr = 245.25 | Dx = 1.458 Mg m−3 |
| Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 5036 reflections |
| a = 5.2901 (2) Å | θ = 3.1–31.4° |
| b = 6.6435 (3) Å | µ = 0.11 mm−1 |
| c = 31.7823 (11) Å | T = 89 K |
| V = 1116.98 (8) Å3 | Rectangular, colourless |
| Z = 4 | 0.30 × 0.23 × 0.04 mm |
| Bruker APEXII CCD area-detector diffractometer | 2185 independent reflections |
| Radiation source: fine-focus sealed tube | 1980 reflections with I > 2σ(I) |
| graphite | Rint = 0.049 |
| ω scans | θmax = 31.5°, θmin = 1.3° |
| Absorption correction: multi-scan (SADABS; Bruker, 2006) | h = −7→7 |
| Tmin = 0.853, Tmax = 0.996 | k = −8→9 |
| 19727 measured reflections | l = −46→45 |
| 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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.096 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0587P)2 + 0.1314P] where P = (Fo2 + 2Fc2)/3 |
| 2185 reflections | (Δ/σ)max < 0.001 |
| 168 parameters | Δρmax = 0.37 e Å−3 |
| 0 restraints | Δρmin = −0.24 e Å−3 |
| C14H12FNO2 | V = 1116.98 (8) Å3 |
| Mr = 245.25 | Z = 4 |
| Orthorhombic, P212121 | Mo Kα radiation |
| a = 5.2901 (2) Å | µ = 0.11 mm−1 |
| b = 6.6435 (3) Å | T = 89 K |
| c = 31.7823 (11) Å | 0.30 × 0.23 × 0.04 mm |
| Bruker APEXII CCD area-detector diffractometer | 2185 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2006) | 1980 reflections with I > 2σ(I) |
| Tmin = 0.853, Tmax = 0.996 | Rint = 0.049 |
| 19727 measured reflections | θmax = 31.5° |
| R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.096 | Δρmax = 0.37 e Å−3 |
| S = 1.06 | Δρmin = −0.24 e Å−3 |
| 2185 reflections | Absolute structure: ? |
| 168 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| N1 | 0.8287 (2) | 0.30490 (19) | 0.12515 (4) | 0.0120 (2) | |
| H1N | 0.681 (4) | 0.274 (3) | 0.1327 (6) | 0.018 (5)* | |
| C1 | 1.0253 (3) | 0.1910 (2) | 0.13830 (4) | 0.0122 (3) | |
| O1 | 1.2460 (2) | 0.21863 (18) | 0.12733 (3) | 0.0195 (2) | |
| C2 | 0.9628 (3) | 0.0195 (2) | 0.16750 (4) | 0.0113 (2) | |
| C3 | 0.7617 (3) | 0.0129 (2) | 0.19568 (4) | 0.0138 (3) | |
| F1 | 0.60670 (19) | 0.17461 (15) | 0.19944 (3) | 0.0211 (2) | |
| C4 | 0.7144 (3) | −0.1504 (3) | 0.22153 (4) | 0.0172 (3) | |
| H4 | 0.5746 | −0.1494 | 0.2403 | 0.021* | |
| C5 | 0.8740 (3) | −0.3153 (2) | 0.21964 (5) | 0.0175 (3) | |
| H5 | 0.8427 | −0.4295 | 0.2369 | 0.021* | |
| C6 | 1.0809 (3) | −0.3137 (2) | 0.19238 (5) | 0.0176 (3) | |
| H6 | 1.1921 | −0.4259 | 0.1912 | 0.021* | |
| C7 | 1.1234 (3) | −0.1472 (2) | 0.16695 (4) | 0.0151 (3) | |
| H7 | 1.2656 | −0.1467 | 0.1487 | 0.018* | |
| C8 | 0.8450 (3) | 0.4821 (2) | 0.10044 (4) | 0.0109 (2) | |
| C9 | 0.6527 (3) | 0.6247 (2) | 0.10514 (4) | 0.0124 (3) | |
| H9 | 0.5154 | 0.5977 | 0.1236 | 0.015* | |
| C10 | 0.6600 (3) | 0.8048 (2) | 0.08330 (4) | 0.0127 (3) | |
| H10 | 0.5290 | 0.9010 | 0.0869 | 0.015* | |
| C11 | 0.8609 (3) | 0.8447 (2) | 0.05591 (4) | 0.0113 (3) | |
| C12 | 1.0490 (3) | 0.7011 (2) | 0.05019 (4) | 0.0120 (3) | |
| H12 | 1.1830 | 0.7261 | 0.0310 | 0.014* | |
| C13 | 1.0418 (3) | 0.5203 (2) | 0.07255 (4) | 0.0123 (3) | |
| H13 | 1.1716 | 0.4232 | 0.0687 | 0.015* | |
| O2 | 0.8549 (2) | 1.02823 (15) | 0.03604 (3) | 0.0144 (2) | |
| C14 | 1.0690 (3) | 1.0759 (2) | 0.01050 (5) | 0.0159 (3) | |
| H14A | 1.2233 | 1.0662 | 0.0274 | 0.024* | |
| H14B | 1.0517 | 1.2132 | −0.0004 | 0.024* | |
| H14C | 1.0788 | 0.9811 | −0.0131 | 0.024* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0097 (5) | 0.0108 (5) | 0.0155 (5) | 0.0003 (5) | 0.0019 (4) | 0.0030 (4) |
| C1 | 0.0124 (6) | 0.0103 (6) | 0.0138 (6) | −0.0004 (5) | 0.0005 (5) | 0.0013 (5) |
| O1 | 0.0117 (5) | 0.0212 (6) | 0.0255 (5) | 0.0005 (4) | 0.0013 (4) | 0.0099 (5) |
| C2 | 0.0125 (6) | 0.0102 (6) | 0.0112 (5) | −0.0008 (5) | −0.0003 (5) | 0.0000 (5) |
| C3 | 0.0124 (6) | 0.0157 (6) | 0.0132 (6) | 0.0011 (5) | −0.0009 (5) | −0.0002 (5) |
| F1 | 0.0214 (5) | 0.0231 (5) | 0.0189 (4) | 0.0094 (4) | 0.0071 (4) | 0.0027 (4) |
| C4 | 0.0154 (6) | 0.0228 (8) | 0.0134 (6) | −0.0033 (6) | 0.0003 (5) | 0.0036 (6) |
| C5 | 0.0194 (7) | 0.0161 (7) | 0.0169 (6) | −0.0054 (6) | −0.0028 (5) | 0.0056 (6) |
| C6 | 0.0198 (7) | 0.0132 (7) | 0.0200 (6) | 0.0019 (6) | −0.0024 (6) | 0.0027 (6) |
| C7 | 0.0159 (6) | 0.0139 (6) | 0.0156 (6) | 0.0020 (6) | 0.0005 (5) | 0.0006 (5) |
| C8 | 0.0117 (6) | 0.0087 (5) | 0.0122 (5) | 0.0001 (5) | −0.0013 (5) | 0.0005 (5) |
| C9 | 0.0108 (6) | 0.0125 (6) | 0.0140 (6) | 0.0000 (5) | 0.0022 (5) | −0.0004 (5) |
| C10 | 0.0116 (6) | 0.0114 (6) | 0.0150 (6) | 0.0013 (5) | 0.0006 (5) | −0.0002 (5) |
| C11 | 0.0124 (6) | 0.0091 (6) | 0.0123 (5) | −0.0005 (5) | −0.0018 (5) | 0.0008 (5) |
| C12 | 0.0110 (5) | 0.0123 (6) | 0.0127 (5) | 0.0003 (5) | 0.0010 (5) | 0.0009 (5) |
| C13 | 0.0119 (6) | 0.0112 (6) | 0.0139 (6) | 0.0020 (5) | 0.0013 (5) | 0.0001 (5) |
| O2 | 0.0145 (5) | 0.0108 (5) | 0.0178 (5) | 0.0019 (4) | 0.0029 (4) | 0.0042 (4) |
| C14 | 0.0146 (6) | 0.0133 (6) | 0.0199 (6) | −0.0009 (6) | 0.0029 (6) | 0.0047 (5) |
| N1—C1 | 1.3522 (19) | C8—C13 | 1.3909 (18) |
| N1—C8 | 1.4177 (17) | C8—C9 | 1.3980 (19) |
| N1—H1N | 0.84 (2) | C9—C10 | 1.3835 (19) |
| C1—O1 | 1.2317 (17) | C9—H9 | 0.9500 |
| C1—C2 | 1.5066 (19) | C10—C11 | 1.3992 (19) |
| C2—C3 | 1.3914 (19) | C10—H10 | 0.9500 |
| C2—C7 | 1.396 (2) | C11—O2 | 1.3734 (16) |
| C3—F1 | 1.3567 (17) | C11—C12 | 1.3902 (19) |
| C3—C4 | 1.384 (2) | C12—C13 | 1.3959 (19) |
| C4—C5 | 1.384 (2) | C12—H12 | 0.9500 |
| C4—H4 | 0.9500 | C13—H13 | 0.9500 |
| C5—C6 | 1.396 (2) | O2—C14 | 1.4289 (18) |
| C5—H5 | 0.9500 | C14—H14A | 0.9800 |
| C6—C7 | 1.388 (2) | C14—H14B | 0.9800 |
| C6—H6 | 0.9500 | C14—H14C | 0.9800 |
| C7—H7 | 0.9500 | ||
| C1—N1—C8 | 126.09 (12) | C13—C8—N1 | 123.38 (12) |
| C1—N1—H1N | 119.3 (14) | C9—C8—N1 | 117.36 (12) |
| C8—N1—H1N | 114.6 (14) | C10—C9—C8 | 120.82 (13) |
| O1—C1—N1 | 123.93 (13) | C10—C9—H9 | 119.6 |
| O1—C1—C2 | 119.66 (13) | C8—C9—H9 | 119.6 |
| N1—C1—C2 | 116.40 (12) | C9—C10—C11 | 119.81 (13) |
| C3—C2—C7 | 116.65 (13) | C9—C10—H10 | 120.1 |
| C3—C2—C1 | 126.02 (13) | C11—C10—H10 | 120.1 |
| C7—C2—C1 | 117.31 (12) | O2—C11—C12 | 124.45 (12) |
| F1—C3—C4 | 117.34 (13) | O2—C11—C10 | 115.90 (12) |
| F1—C3—C2 | 119.61 (13) | C12—C11—C10 | 119.66 (12) |
| C4—C3—C2 | 123.02 (14) | C11—C12—C13 | 120.29 (13) |
| C3—C4—C5 | 118.98 (14) | C11—C12—H12 | 119.9 |
| C3—C4—H4 | 120.5 | C13—C12—H12 | 119.9 |
| C5—C4—H4 | 120.5 | C8—C13—C12 | 120.13 (13) |
| C4—C5—C6 | 119.95 (14) | C8—C13—H13 | 119.9 |
| C4—C5—H5 | 120.0 | C12—C13—H13 | 119.9 |
| C6—C5—H5 | 120.0 | C11—O2—C14 | 116.09 (11) |
| C7—C6—C5 | 119.60 (14) | O2—C14—H14A | 109.5 |
| C7—C6—H6 | 120.2 | O2—C14—H14B | 109.5 |
| C5—C6—H6 | 120.2 | H14A—C14—H14B | 109.5 |
| C6—C7—C2 | 121.77 (14) | O2—C14—H14C | 109.5 |
| C6—C7—H7 | 119.1 | H14A—C14—H14C | 109.5 |
| C2—C7—H7 | 119.1 | H14B—C14—H14C | 109.5 |
| C13—C8—C9 | 119.26 (13) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O1i | 0.84 (2) | 2.34 (2) | 3.1366 (17) | 158.5 (17) |
| C4—H4···F1ii | 0.95 | 2.44 | 3.2472 (17) | 143 |
| C14—H14B···O2iii | 0.98 | 2.61 | 3.3753 (18) | 135 |
| Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+1/2; (iii) x+1/2, −y+5/2, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O1i | 0.84 (2) | 2.34 (2) | 3.1366 (17) | 158.5 (17) |
| C4—H4···F1ii | 0.95 | 2.44 | 3.2472 (17) | 143 |
| C14—H14B···O2iii | 0.98 | 2.61 | 3.3753 (18) | 135 |
| Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+1/2; (iii) x+1/2, −y+5/2, −z. |
MA gratefully acknowledges a research scholarship from the HEC, Islamabad, under the HEC Indigenous PhD Scholarship 5000 Scheme. We also thank the University of Otago for the purchase of the diffractometer.
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The benzanilide core is present in compounds with a wide range of biological activity and benzanilides and benzamides are also used extensively in organic synthesis (Saeed et al., 2008). Various N-substituted benzamides exhibit potent antiemetic activity (Vega-Noverola et al., 1989). A one-pot conversion of 2-nitro-n-arylbenzamides to 2,3-dihydro-1H-quinazoline-4-ones has also been reported (Yoo et al., 2005).
As part of our work on the structure of benzanilides and related compounds, we report here the structure of the title 2-fluorobenzamide derivative, I, Fig 1. In the structure of (I), the C2···C7 and C8···C13 rings are inclined at 27.06 (7)° and 23.86 (7)° respectively to the C2/C1/O1/N1/C8 amide portion of the molecule and at 3.46 (9)° to one another. The methoxy substituent lies close to the methoxybenzene ring plane with a maximum deviation of 0.152 (3) Å for C14. N-aryl 2-fluorobenzamide derivatives are reasonably common and bond distances and angles in the present molecule agree well with those in similar structures (see for example Saeed et al. 2008, Chopra & Guru Row, 2008, Donnelly et al. 2008, Cockroft et al. (2007), Spitaleri et al. 2004).
In the crystal structure intermolecular N1—H1N···O1 hydrogen bonds link molecules into rows along a. Weak C—H···O and C—H···F interactions further stabilize the packing, forming corrugated sheets in the bc plane (Table 1 and Fig.2).