2-Fluoro-N-(4-methoxy­phen­yl)benzamide

Saeed, A.; Khera, R.A.; Arfan, M.; Simpson, J.; Stanley, R.G.

doi:10.1107/S1600536809008927

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o802-o803

doi:10.1107/S1600536809008927

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2-Fluoro-N-(4-methoxyphenyl)benzamide

Aamer Saeed,^a ^* Rasheed Ahmad Khera,^a Madiah Arfan,^a Jim Simpson ^b and Roderick G. Stanley ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 3 March 2009; accepted 11 March 2009; online 19 March 2009)

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—H⋯O and C—H⋯F interactions further stabilize the packing, forming corrugated sheets in the bc plane.

Related literature

For the biological activity of benzamides and related compounds and their use in organic synthesis, see: Vega-Noverola et al. (1989 ); Yoo et al. (2005 ); Saeed et al. (2008 ). For related structures, see: Saeed et al. (2008); Chopra & Guru Row (2008 ); Donnelly et al. (2008 ); Cockroft et al. (2007 ); Spitaleri et al. (2004 ).

Experimental

Crystal data

C₁₄H₁₂FNO₂
M_r = 245.25
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.2901 (2) Å
b = 6.6435 (3) Å
c = 31.7823 (11) Å
V = 1116.98 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 89 K
0.30 × 0.23 × 0.04 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.853, T_max = 0.996
19727 measured reflections
2185 independent reflections
1980 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.096
S = 1.06
2185 reflections
168 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z]$ . Cg2 is the centroid of the C3–C8 benzene ring.

Data collection: APEX2 (Bruker 2006); cell refinement: APEX2 and SAINT (Bruker 2006); data reduction: SAINT; 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; molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008927/si2159sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809008927/si2159Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

For the biological activity of benzamides and related compounds and their use in organic synthesis, see: Vega-Noverola et al. (1989); Yoo et al. (2005); Saeed et al. (2008). For related structures, see: Saeed et al. (2008); Chopra & Guru Row (2008); Donnelly et al. (2008); Cockroft et al. (2007); Spitaleri et al. (2004). Cg2 is the centroid of the C3–C8 benzene ring.

Experimental top

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%

Computing details top

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).

Figures top

	Fig. 1. The structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level.
	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.

2-Fluoro-N-(4-methoxyphenyl)benzamide top

Crystal data top

C₁₄H₁₂FNO₂	F(000) = 512
M_r = 245.25	D_x = 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

Data collection top

Bruker APEXII CCD area-detector diffractometer	2185 independent reflections
Radiation source: fine-focus sealed tube	1980 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ω scans	θ_max = 31.5°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −7→7
T_min = 0.853, T_max = 0.996	k = −8→9
19727 measured reflections	l = −46→45

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)] = 0.035	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(F_o²) + (0.0587P)² + 0.1314P] where P = (F_o² + 2F_c²)/3
2185 reflections	(Δ/σ)_max < 0.001
168 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₁₂FNO₂	V = 1116.98 (8) Å³
M_r = 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

Data collection top

Bruker APEXII CCD area-detector diffractometer	2185 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	1980 reflections with I > 2σ(I)
T_min = 0.853, T_max = 0.996	R_int = 0.049
19727 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.37 e Å⁻³
2185 reflections	Δρ_min = −0.24 e Å⁻³
168 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂FNO₂
M_r	245.25
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	89
a, b, c (Å)	5.2901 (2), 6.6435 (3), 31.7823 (11)
V (Å³)	1116.98 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.23 × 0.04

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.853, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	19727, 2185, 1980
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.735

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.096, 1.06
No. of reflections	2185
No. of parameters	168
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.24

Computer programs: , APEX2 (Bruker 2006) and SAINT (Bruker 2006), SAINT (Bruker 2006), SHELXS97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999), SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

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)	142.7
C14—H14B···O2ⁱⁱⁱ	0.98	2.61	3.3753 (18)	135.1

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+1/2; (iii) x+1/2, −y+5/2, −z.

Acknowledgements

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.

References

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