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Acta Crystallogr Sect E Struct Rep Online. 2012 May 1; 68(Pt 5): o1348.
Published online 2012 April 13. doi:  10.1107/S160053681201416X
PMCID: PMC3344482

N-(3-Chloro-4-fluoro­phen­yl)acetamide

Abstract

In the title compound, C8H7ClFNO, the dihedral angle between the benzene ring and the acetamide side chain is 5.47 (6)°. An S(6) ring motif is formed via an intra­molecular C—H(...)O hydrogen bond. In the crystal, N—H(...)O hydrogen bonds link the mol­ecules into C(4) chains along [001].

Related literature  

For background to acetamides, see: Khan et al. (2010 [triangle]); Tahir & Shad (2011 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For a related structure, see: Rosli et al. (2007 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

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Object name is e-68-o1348-scheme1.jpg

Experimental  

Crystal data  

  • C8H7ClFNO
  • M r = 187.60
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-o1348-efi1.jpg
  • a = 7.6776 (4) Å
  • b = 12.7671 (7) Å
  • c = 9.8130 (4) Å
  • β = 124.432 (3)°
  • V = 793.35 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.44 mm−1
  • T = 100 K
  • 0.33 × 0.29 × 0.15 mm

Data collection  

  • Bruker SMART APEXII DUO CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.869, T max = 0.937
  • 14562 measured reflections
  • 3971 independent reflections
  • 3173 reflections with I > 2σ(I)
  • R int = 0.035

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.143
  • S = 1.09
  • 3971 reflections
  • 110 parameters
  • H-atom parameters constrained
  • Δρmax = 1.32 e Å−3
  • Δρmin = −0.50 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201416X/hb6705sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201416X/hb6705Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201416X/hb6705Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PFIZIK/811160). BN thanks the UGC SAP for financial assistance for the purchase of chemicals. DNS thanks Mangalore University for research facilities.

supplementary crystallographic information

Comment

To complement earlier studies of acetamides (Khan et al., 2010; Tahir & Shad, 2011), we report herein the crystal structure of the title compound.

In the title compound (Fig. 1), an S(6) ring motif (Bernstein et al., 1995) is formed via intramolecular C1—H1A···O1 hydrogen bond (Table 1). Bond lengths and angles are within the normal ranges and are comparable with the related structure (Rosli et al., 2007).

In the crystal (Fig. 2), N1—H1···O1 hydrogen bonds (Table 1) link the molecules to form chains along the c axis.

Experimental

3-Chloro-4-fluoro aniline (0.145 g, 1 mmol) was dissolved in acetic acid (20 mL) and refluxed for 4 h. The solution was then cooled and poured into 100 ml of ice-cold water with stirring. The precipitate obtained was filtered, washed with water and dried. Orange blocks were grown from DMF solution by the slow evaporation method. M. P.: 384 K.

Refinement

N-bound H atoms were located from the difference Fourier map and were refined with a riding model with Uiso(H) = 1.2 Ueq(N) [N–H = 0.9003 Å]. The remaining H atoms were positioned geometrically and refined with a riding model with Uiso(H) = 1.2 or 1.5 Ueq(C) [C–H = 0.95 or 0.98 Å]. A rotating group model was applied to the methyl groups. In the final refinement, five outliners were omitted, -3 8 2, -1 0 1, -3 8 1, 1 0 0 and -1 0 4. In the final difference Fourier map, the highest peak and the deepest hole are 0.83 and 0.71Å from atom Cl1.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids. Dashed line indicates the intramolecular hydrogen bond.
Fig. 2.
The crystal packing of the title compound, viewed along the a axis, showing the chains along the c axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Crystal data

C8H7ClFNOF(000) = 384
Mr = 187.60Dx = 1.571 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5541 reflections
a = 7.6776 (4) Åθ = 3.0–36.8°
b = 12.7671 (7) ŵ = 0.44 mm1
c = 9.8130 (4) ÅT = 100 K
β = 124.432 (3)°Block, orange
V = 793.35 (7) Å30.33 × 0.29 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEXII DUO CCD diffractometer3971 independent reflections
Radiation source: fine-focus sealed tube3173 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
[var phi] and ω scansθmax = 36.9°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −12→12
Tmin = 0.869, Tmax = 0.937k = −21→17
14562 measured reflectionsl = −14→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0844P)2 + 0.1402P] where P = (Fo2 + 2Fc2)/3
3971 reflections(Δ/σ)max < 0.001
110 parametersΔρmax = 1.32 e Å3
0 restraintsΔρmin = −0.50 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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)

xyzUiso*/Ueq
Cl10.32215 (5)−0.12199 (2)0.38846 (3)0.02251 (9)
F10.31780 (12)−0.24025 (5)0.13350 (9)0.02207 (16)
O10.18905 (15)0.24972 (7)0.21236 (10)0.02070 (17)
N10.20506 (15)0.18521 (7)0.00234 (11)0.01588 (16)
H10.19790.2007−0.09020.019*
C10.27231 (17)0.03769 (8)0.18824 (12)0.01625 (18)
H1A0.27660.08310.26680.019*
C20.29704 (17)−0.06971 (8)0.21576 (13)0.01634 (18)
C30.29615 (17)−0.13592 (8)0.10379 (13)0.01655 (18)
C40.27098 (18)−0.09670 (9)−0.03746 (13)0.01834 (19)
H4A0.2733−0.1423−0.11290.022*
C50.24229 (17)0.01024 (9)−0.06795 (13)0.01731 (19)
H5A0.22330.0377−0.16550.021*
C60.24111 (16)0.07801 (8)0.04398 (12)0.01421 (17)
C70.17661 (17)0.26277 (8)0.08257 (13)0.01566 (18)
C80.1266 (2)0.36891 (9)0.00122 (14)0.0196 (2)
H8A0.24670.41600.06870.029*
H8B0.00130.3977−0.00910.029*
H8C0.09920.3619−0.10880.029*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.03690 (18)0.01515 (13)0.02113 (14)0.00050 (9)0.01980 (13)0.00337 (8)
F10.0318 (4)0.0111 (3)0.0247 (3)0.0014 (2)0.0167 (3)0.0004 (2)
O10.0340 (4)0.0164 (4)0.0183 (3)0.0011 (3)0.0188 (3)−0.0001 (3)
N10.0246 (4)0.0120 (3)0.0155 (3)−0.0003 (3)0.0140 (3)0.0001 (3)
C10.0230 (5)0.0126 (4)0.0160 (4)−0.0006 (3)0.0128 (4)−0.0006 (3)
C20.0214 (4)0.0136 (4)0.0162 (4)−0.0009 (3)0.0120 (3)0.0003 (3)
C30.0204 (4)0.0116 (4)0.0183 (4)0.0000 (3)0.0114 (4)−0.0005 (3)
C40.0243 (5)0.0152 (4)0.0180 (4)0.0002 (3)0.0134 (4)−0.0029 (3)
C50.0238 (5)0.0153 (4)0.0165 (4)−0.0002 (3)0.0136 (4)−0.0011 (3)
C60.0183 (4)0.0122 (4)0.0148 (4)−0.0007 (3)0.0109 (3)−0.0003 (3)
C70.0201 (4)0.0134 (4)0.0159 (4)−0.0007 (3)0.0116 (3)−0.0003 (3)
C80.0281 (5)0.0136 (4)0.0211 (5)0.0011 (3)0.0163 (4)0.0019 (3)

Geometric parameters (Å, º)

Cl1—C21.7278 (11)C3—C41.3807 (15)
F1—C31.3535 (12)C4—C51.3884 (15)
O1—C71.2335 (13)C4—H4A0.9500
N1—C71.3573 (14)C5—C61.4023 (14)
N1—C61.4102 (14)C5—H5A0.9500
N1—H10.9003C7—C81.5081 (15)
C1—C21.3896 (15)C8—H8A0.9800
C1—C61.3938 (14)C8—H8B0.9800
C1—H1A0.9500C8—H8C0.9800
C2—C31.3832 (15)
C7—N1—C6127.56 (9)C4—C5—C6120.56 (10)
C7—N1—H1119.1C4—C5—H5A119.7
C6—N1—H1113.3C6—C5—H5A119.7
C2—C1—C6119.21 (9)C1—C6—C5119.61 (10)
C2—C1—H1A120.4C1—C6—N1123.06 (9)
C6—C1—H1A120.4C5—C6—N1117.32 (9)
C3—C2—C1120.66 (10)O1—C7—N1123.81 (10)
C3—C2—Cl1119.39 (8)O1—C7—C8121.05 (10)
C1—C2—Cl1119.93 (8)N1—C7—C8115.14 (9)
F1—C3—C4120.24 (9)C7—C8—H8A109.5
F1—C3—C2119.04 (10)C7—C8—H8B109.5
C4—C3—C2120.71 (10)H8A—C8—H8B109.5
C3—C4—C5119.22 (10)C7—C8—H8C109.5
C3—C4—H4A120.4H8A—C8—H8C109.5
C5—C4—H4A120.4H8B—C8—H8C109.5
C6—C1—C2—C31.61 (16)C2—C1—C6—C5−2.14 (16)
C6—C1—C2—Cl1−176.64 (8)C2—C1—C6—N1177.04 (10)
C1—C2—C3—F1−179.12 (10)C4—C5—C6—C11.00 (16)
Cl1—C2—C3—F1−0.85 (14)C4—C5—C6—N1−178.22 (10)
C1—C2—C3—C40.09 (16)C7—N1—C6—C1−6.20 (17)
Cl1—C2—C3—C4178.35 (9)C7—N1—C6—C5172.99 (10)
F1—C3—C4—C5177.95 (10)C6—N1—C7—O13.71 (18)
C2—C3—C4—C5−1.24 (17)C6—N1—C7—C8−176.05 (10)
C3—C4—C5—C60.69 (17)

Hydrogen-bond geometry (Å, º)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.902.002.8996 (12)174
C1—H1A···O10.952.202.8222 (14)122

Symmetry code: (i) x, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6705).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.
  • Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.
  • Khan, F. N., Roopan, S. M., Malathi, N., Hathwar, V. R. & Akkurt, M. (2010). Acta Cryst. E66, o2043–o2044. [PMC free article] [PubMed]
  • Rosli, M. M., Karthikeyan, M. S., Fun, H.-K., Razak, I. A. & Patil, P. S. (2007). Acta Cryst. E63, o67–o68.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Tahir, M. N. & Shad, H. A. (2011). Acta Cryst. E67, o443. [PMC free article] [PubMed]

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