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

doi:10.1107/S160053681201416X

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

Hoong-Kun Fun,^a^*^‡ Wan-Sin Loh,^a^§ Divya N. Shetty,^b B. Narayana,^b and B. K. Sarojini^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia

^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India

^cDepartment of Chemistry, P.A. College of Engineering, Nadupadavu, Mangalore 574 153, India

Correspondence e-mail: hkfun/at/usm.my

^‡Thomson Reuters ResearcherID: A-3561-2009.

^§Thomson Reuters ResearcherID: C-7581-2009.

Received March 26, 2012; Accepted April 1, 2012.

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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

); Tahir & Shad (2011

). For hydrogen-bond motifs, see: Bernstein et al. (1995

). For a related structure, see: Rosli et al. (2007

). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986

An external file that holds a picture, illustration, etc.
Object name is e-68-o1348-scheme1.jpg Object name is e-68-o1348-scheme1.jpg

Experimental

Crystal data

C₈H₇ClFNO
M _r = 187.60
Monoclinic,
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 ) 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
Δρ_max = 1.32 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Data collection: APEX2 (Bruker, 2009

); cell refinement: SAINT (Bruker, 2009

); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008

); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009

Table 1

Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Click here to view.^{(19K, cif)}

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

Click here to view.^{(195K, 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.

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

C₈H₇ClFNO	F(000) = 384
M_r = 187.60	D_x = 1.571 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5541 reflections
a = 7.6776 (4) Å	θ = 3.0–36.8°
b = 12.7671 (7) Å	µ = 0.44 mm⁻¹
c = 9.8130 (4) Å	T = 100 K
β = 124.432 (3)°	Block, orange
V = 793.35 (7) Å³	0.33 × 0.29 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEXII DUO CCD diffractometer	3971 independent reflections
Radiation source: fine-focus sealed tube	3173 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
and ω scans	θ_max = 36.9°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
T_min = 0.869, T_max = 0.937	k = −21→17
14562 measured reflections	l = −14→16

Refinement

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0844P)² + 0.1402P] where P = (F_o² + 2F_c²)/3
3971 reflections	(Δ/σ)_max < 0.001
110 parameters	Δρ_max = 1.32 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

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)

	x	y	z	U_iso*/U_eq
Cl1	0.32215 (5)	−0.12199 (2)	0.38846 (3)	0.02251 (9)
F1	0.31780 (12)	−0.24025 (5)	0.13350 (9)	0.02207 (16)
O1	0.18905 (15)	0.24972 (7)	0.21236 (10)	0.02070 (17)
N1	0.20506 (15)	0.18521 (7)	0.00234 (11)	0.01588 (16)
H1	0.1979	0.2007	−0.0902	0.019*
C1	0.27231 (17)	0.03769 (8)	0.18824 (12)	0.01625 (18)
H1A	0.2766	0.0831	0.2668	0.019*
C2	0.29704 (17)	−0.06971 (8)	0.21576 (13)	0.01634 (18)
C3	0.29615 (17)	−0.13592 (8)	0.10379 (13)	0.01655 (18)
C4	0.27098 (18)	−0.09670 (9)	−0.03746 (13)	0.01834 (19)
H4A	0.2733	−0.1423	−0.1129	0.022*
C5	0.24229 (17)	0.01024 (9)	−0.06795 (13)	0.01731 (19)
H5A	0.2233	0.0377	−0.1655	0.021*
C6	0.24111 (16)	0.07801 (8)	0.04398 (12)	0.01421 (17)
C7	0.17661 (17)	0.26277 (8)	0.08257 (13)	0.01566 (18)
C8	0.1266 (2)	0.36891 (9)	0.00122 (14)	0.0196 (2)
H8A	0.2467	0.4160	0.0687	0.029*
H8B	0.0013	0.3977	−0.0091	0.029*
H8C	0.0992	0.3619	−0.1088	0.029*

Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.03690 (18)	0.01515 (13)	0.02113 (14)	0.00050 (9)	0.01980 (13)	0.00337 (8)
F1	0.0318 (4)	0.0111 (3)	0.0247 (3)	0.0014 (2)	0.0167 (3)	0.0004 (2)
O1	0.0340 (4)	0.0164 (4)	0.0183 (3)	0.0011 (3)	0.0188 (3)	−0.0001 (3)
N1	0.0246 (4)	0.0120 (3)	0.0155 (3)	−0.0003 (3)	0.0140 (3)	0.0001 (3)
C1	0.0230 (5)	0.0126 (4)	0.0160 (4)	−0.0006 (3)	0.0128 (4)	−0.0006 (3)
C2	0.0214 (4)	0.0136 (4)	0.0162 (4)	−0.0009 (3)	0.0120 (3)	0.0003 (3)
C3	0.0204 (4)	0.0116 (4)	0.0183 (4)	0.0000 (3)	0.0114 (4)	−0.0005 (3)
C4	0.0243 (5)	0.0152 (4)	0.0180 (4)	0.0002 (3)	0.0134 (4)	−0.0029 (3)
C5	0.0238 (5)	0.0153 (4)	0.0165 (4)	−0.0002 (3)	0.0136 (4)	−0.0011 (3)
C6	0.0183 (4)	0.0122 (4)	0.0148 (4)	−0.0007 (3)	0.0109 (3)	−0.0003 (3)
C7	0.0201 (4)	0.0134 (4)	0.0159 (4)	−0.0007 (3)	0.0116 (3)	−0.0003 (3)
C8	0.0281 (5)	0.0136 (4)	0.0211 (5)	0.0011 (3)	0.0163 (4)	0.0019 (3)

Geometric parameters (Å, º)

Cl1—C2	1.7278 (11)	C3—C4	1.3807 (15)
F1—C3	1.3535 (12)	C4—C5	1.3884 (15)
O1—C7	1.2335 (13)	C4—H4A	0.9500
N1—C7	1.3573 (14)	C5—C6	1.4023 (14)
N1—C6	1.4102 (14)	C5—H5A	0.9500
N1—H1	0.9003	C7—C8	1.5081 (15)
C1—C2	1.3896 (15)	C8—H8A	0.9800
C1—C6	1.3938 (14)	C8—H8B	0.9800
C1—H1A	0.9500	C8—H8C	0.9800
C2—C3	1.3832 (15)

C7—N1—C6	127.56 (9)	C4—C5—C6	120.56 (10)
C7—N1—H1	119.1	C4—C5—H5A	119.7
C6—N1—H1	113.3	C6—C5—H5A	119.7
C2—C1—C6	119.21 (9)	C1—C6—C5	119.61 (10)
C2—C1—H1A	120.4	C1—C6—N1	123.06 (9)
C6—C1—H1A	120.4	C5—C6—N1	117.32 (9)
C3—C2—C1	120.66 (10)	O1—C7—N1	123.81 (10)
C3—C2—Cl1	119.39 (8)	O1—C7—C8	121.05 (10)
C1—C2—Cl1	119.93 (8)	N1—C7—C8	115.14 (9)
F1—C3—C4	120.24 (9)	C7—C8—H8A	109.5
F1—C3—C2	119.04 (10)	C7—C8—H8B	109.5
C4—C3—C2	120.71 (10)	H8A—C8—H8B	109.5
C3—C4—C5	119.22 (10)	C7—C8—H8C	109.5
C3—C4—H4A	120.4	H8A—C8—H8C	109.5
C5—C4—H4A	120.4	H8B—C8—H8C	109.5

C6—C1—C2—C3	1.61 (16)	C2—C1—C6—C5	−2.14 (16)
C6—C1—C2—Cl1	−176.64 (8)	C2—C1—C6—N1	177.04 (10)
C1—C2—C3—F1	−179.12 (10)	C4—C5—C6—C1	1.00 (16)
Cl1—C2—C3—F1	−0.85 (14)	C4—C5—C6—N1	−178.22 (10)
C1—C2—C3—C4	0.09 (16)	C7—N1—C6—C1	−6.20 (17)
Cl1—C2—C3—C4	178.35 (9)	C7—N1—C6—C5	172.99 (10)
F1—C3—C4—C5	177.95 (10)	C6—N1—C7—O1	3.71 (18)
C2—C3—C4—C5	−1.24 (17)	C6—N1—C7—C8	−176.05 (10)
C3—C4—C5—C6	0.69 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.90	2.00	2.8996 (12)	174
C1—H1A···O1	0.95	2.20	2.8222 (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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