2-(4-Bromo­phen­yl)-N-(3-chloro-4-fluoro­phen­yl)acetamide

Fun, H.-K.; Quah, C.K.; Nayak, P.S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812032977

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2558

https://doi.org/10.1107/S1600536812032977

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2-(4-Bromophenyl)-N-(3-chloro-4-fluorophenyl)acetamide

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Prakash S. Nayak,^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, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 10 July 2012; accepted 20 July 2012; online 25 July 2012)

In the title compound, C₁₄H₁₀BrClFNO, the benzene rings form a dihedral angle of 64.0 (2)°. In the crystal, molecules are linked via intermolecular N—H⋯O, C—H⋯O, C—H⋯Cl and C—H⋯F hydrogen bonds into layers parallel to (001). The crystal was refined as a merohedral twin with a 0.935 (114):0.065 (14) domain ratio.

Related literature

For general background to the title compound and for related structures, see: Fun et al. (2011a ,b , 2012a ,b ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₄H₁₀BrClFNO
M_r = 342.59
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.9120 (5) Å
b = 6.3131 (6) Å
c = 42.517 (4) Å
V = 1318.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 3.32 mm⁻¹
T = 100 K
0.30 × 0.17 × 0.07 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.440, T_max = 0.806
10866 measured reflections
4737 independent reflections
4358 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.120
S = 1.15
4737 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −1.82 e Å⁻³
Absolute structure: Flack (1983 ), 1929 Friedel pairs
Flack parameter: 0.065 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.88	1.97	2.844 (5)	172
C2—H2A⋯O1ⁱⁱ	0.95	2.58	3.321 (5)	135
C10—H10A⋯Cl1ⁱⁱⁱ	0.95	2.67	3.583 (5)	160
C11—H11A⋯F1^iv	0.95	2.52	3.443 (6)	165
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x-1, y+1, z; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812032977/rz2791sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812032977/rz2791Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812032977/rz2791Isup3.cml

checkCIF report

Comment top

In continuation of our work on the synthesis of amides (Fun et al., 2011a, 2011b, 2012a, 2012b), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the two benzene rings (C1-C6, C9-C14) form a dihedral angle of 64.0 (2)°. Bond lengths and angles are within normal ranges and are comparable to those found in related structures (Fun et al., 2011a, 2011b, 2012a, 2012b). In the crystal structure (Fig. 2), molecules are linked via intermolecular N1–H1N1···O1, C2–H2A···O1, C10–H10A···Cl1 and C11–H11A···F1 hydrogen bonds (Table 1) into two-dimensional layers parallel to (001).

Related literature top

For general background to the title compound and for related structures, see: Fun et al. (2011a,b, 2012a,b). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

4-Bromophenylacetic acid (0.213 g, 1 mmol), 3-chloro-4-fluoroaniline (0.145 g, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) were dissolved in dichloromethane (20 mL). The mixture was stirred in presence of triethylamine at 273 K for about 3 h, poured into 100 mL of ice-cold aqueous hydrochloric acid with stirring and was then extracted thrice with dichloromethane. The organic layer was washed with a saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound. Single crystals were grown from acetone and toluene (1:1 v/v) mixture by the slow evaporation method (m.p.: 415-417 K).

Structure description top

In continuation of our work on the synthesis of amides (Fun et al., 2011a, 2011b, 2012a, 2012b), we report herein the crystal structure of the title compound.

For general background to the title compound and for related structures, see: Fun et al. (2011a,b, 2012a,b). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

2-(4-Bromophenyl)-N-(3-chloro-4-fluorophenyl)acetamide top

Crystal data top

C₁₄H₁₀BrClFNO	F(000) = 680
M_r = 342.59	D_x = 1.726 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4232 reflections
a = 4.9120 (5) Å	θ = 3.5–31.8°
b = 6.3131 (6) Å	µ = 3.32 mm⁻¹
c = 42.517 (4) Å	T = 100 K
V = 1318.4 (2) Å³	Plate, colourless
Z = 4	0.30 × 0.17 × 0.07 mm

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	4737 independent reflections
Radiation source: fine-focus sealed tube	4358 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 32.5°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
T_min = 0.440, T_max = 0.806	k = −9→9
10866 measured reflections	l = −46→63

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0038P)² + 3.9457P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max = 0.001
4737 reflections	Δρ_max = 0.86 e Å⁻³
173 parameters	Δρ_min = −1.82 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1929 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.065 (14)

Crystal data top

C₁₄H₁₀BrClFNO	V = 1318.4 (2) Å³
M_r = 342.59	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.9120 (5) Å	µ = 3.32 mm⁻¹
b = 6.3131 (6) Å	T = 100 K
c = 42.517 (4) Å	0.30 × 0.17 × 0.07 mm

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	4737 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4358 reflections with I > 2σ(I)
T_min = 0.440, T_max = 0.806	R_int = 0.032
10866 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.120	Δρ_max = 0.86 e Å⁻³
S = 1.15	Δρ_min = −1.82 e Å⁻³
4737 reflections	Absolute structure: Flack (1983), 1929 Friedel pairs
173 parameters	Absolute structure parameter: 0.065 (14)
0 restraints

Special details top

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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	0.05032 (9)	1.14272 (6)	0.026647 (9)	0.01959 (9)
Cl1	1.2503 (4)	−0.31406 (18)	0.19870 (3)	0.0379 (3)
F1	0.8185 (7)	−0.1764 (6)	0.24039 (7)	0.0389 (8)
O1	0.5500 (7)	0.4407 (5)	0.12674 (7)	0.0216 (5)
N1	0.9909 (6)	0.3622 (6)	0.13959 (7)	0.0183 (6)
H1N1	1.1678	0.3812	0.1374	0.022*
C1	0.6150 (9)	0.9292 (7)	0.09204 (10)	0.0206 (8)
H1A	0.6939	0.9808	0.1110	0.025*
C2	0.4185 (9)	1.0515 (6)	0.07644 (9)	0.0195 (8)
H2A	0.3622	1.1843	0.0847	0.023*
C3	0.3096 (8)	0.9750 (6)	0.04902 (9)	0.0158 (7)
C4	0.3851 (9)	0.7798 (6)	0.03669 (10)	0.0185 (7)
H4A	0.3046	0.7284	0.0179	0.022*
C5	0.5801 (9)	0.6617 (6)	0.05240 (9)	0.0189 (7)
H5A	0.6354	0.5291	0.0440	0.023*
C6	0.6964 (9)	0.7335 (6)	0.08025 (10)	0.0182 (7)
C7	0.9099 (8)	0.6042 (6)	0.09676 (10)	0.0204 (8)
H7A	1.0466	0.7010	0.1061	0.025*
H7B	1.0043	0.5142	0.0811	0.025*
C8	0.7943 (8)	0.4641 (6)	0.12252 (9)	0.0157 (7)
C9	0.9335 (9)	0.2242 (6)	0.16520 (9)	0.0179 (7)
C10	0.7350 (10)	0.2685 (8)	0.18765 (11)	0.0268 (9)
H10A	0.6262	0.3923	0.1858	0.032*
C11	0.6968 (10)	0.1312 (10)	0.21275 (11)	0.0320 (10)
H11A	0.5588	0.1590	0.2279	0.038*
C12	0.8580 (11)	−0.0440 (8)	0.21570 (11)	0.0275 (9)
C13	1.0540 (12)	−0.0902 (6)	0.19399 (9)	0.0228 (8)
C14	1.0956 (9)	0.0427 (7)	0.16824 (9)	0.0211 (8)
H14A	1.2313	0.0108	0.1530	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01688 (15)	0.01907 (14)	0.02281 (16)	0.00264 (16)	0.00107 (16)	0.00387 (15)
Cl1	0.0564 (9)	0.0216 (5)	0.0357 (6)	0.0089 (5)	−0.0016 (6)	−0.0003 (4)
F1	0.0354 (18)	0.0496 (19)	0.0316 (14)	−0.0056 (16)	0.0028 (13)	0.0207 (14)
O1	0.0082 (11)	0.0314 (13)	0.0253 (13)	−0.0002 (14)	0.0008 (13)	0.0045 (11)
N1	0.0022 (14)	0.0290 (14)	0.0236 (14)	−0.0016 (13)	0.0004 (10)	0.0048 (14)
C1	0.020 (2)	0.0221 (16)	0.0193 (17)	−0.0013 (15)	0.0019 (15)	−0.0015 (14)
C2	0.017 (2)	0.0183 (15)	0.0229 (17)	0.0020 (16)	0.0024 (16)	−0.0017 (13)
C3	0.0116 (17)	0.0151 (14)	0.0206 (17)	−0.0001 (13)	0.0018 (14)	0.0030 (12)
C4	0.0139 (18)	0.0213 (16)	0.0202 (16)	0.0035 (14)	−0.0002 (14)	−0.0024 (13)
C5	0.0202 (19)	0.0135 (14)	0.0231 (16)	0.0030 (16)	−0.0007 (15)	−0.0006 (13)
C6	0.0142 (18)	0.0204 (16)	0.0200 (18)	0.0003 (15)	0.0013 (15)	0.0015 (14)
C7	0.0114 (19)	0.0263 (19)	0.0235 (17)	0.0004 (14)	0.0028 (14)	0.0065 (14)
C8	0.0067 (15)	0.0216 (16)	0.0187 (17)	−0.0004 (14)	−0.0027 (13)	−0.0020 (13)
C9	0.0082 (15)	0.0261 (16)	0.0194 (16)	−0.0035 (16)	−0.0021 (16)	0.0007 (13)
C10	0.018 (2)	0.038 (2)	0.025 (2)	0.0064 (19)	0.0039 (17)	0.0044 (17)
C11	0.019 (2)	0.051 (3)	0.026 (2)	0.009 (2)	0.0075 (17)	0.011 (2)
C12	0.027 (2)	0.033 (2)	0.023 (2)	−0.007 (2)	−0.0017 (18)	0.0093 (17)
C13	0.027 (2)	0.0179 (15)	0.0234 (17)	−0.0008 (18)	−0.0069 (19)	−0.0003 (12)
C14	0.018 (2)	0.0259 (18)	0.0190 (17)	0.0000 (16)	0.0040 (15)	−0.0017 (14)

Geometric parameters (Å, º) top

Br1—C3	1.910 (4)	C5—C6	1.391 (6)
Cl1—C13	1.723 (4)	C5—H5A	0.9500
F1—C12	1.356 (5)	C6—C7	1.503 (6)
O1—C8	1.222 (5)	C7—C8	1.518 (6)
N1—C8	1.369 (5)	C7—H7A	0.9900
N1—C9	1.423 (5)	C7—H7B	0.9900
N1—H1N1	0.8825	C9—C10	1.393 (6)
C1—C6	1.392 (6)	C9—C14	1.401 (6)
C1—C2	1.403 (6)	C10—C11	1.388 (7)
C1—H1A	0.9500	C10—H10A	0.9500
C2—C3	1.371 (6)	C11—C12	1.366 (7)
C2—H2A	0.9500	C11—H11A	0.9500
C3—C4	1.390 (5)	C12—C13	1.365 (7)
C4—C5	1.385 (6)	C13—C14	1.395 (6)
C4—H4A	0.9500	C14—H14A	0.9500

C8—N1—C9	123.6 (3)	C6—C7—H7B	109.0
C8—N1—H1N1	125.0	C8—C7—H7B	109.0
C9—N1—H1N1	111.2	H7A—C7—H7B	107.8
C6—C1—C2	121.1 (4)	O1—C8—N1	123.9 (4)
C6—C1—H1A	119.5	O1—C8—C7	122.9 (4)
C2—C1—H1A	119.5	N1—C8—C7	113.1 (3)
C3—C2—C1	118.5 (4)	C10—C9—C14	119.9 (4)
C3—C2—H2A	120.8	C10—C9—N1	122.7 (4)
C1—C2—H2A	120.8	C14—C9—N1	117.3 (4)
C2—C3—C4	122.0 (4)	C11—C10—C9	119.8 (4)
C2—C3—Br1	119.2 (3)	C11—C10—H10A	120.1
C4—C3—Br1	118.8 (3)	C9—C10—H10A	120.1
C5—C4—C3	118.7 (4)	C12—C11—C10	119.9 (4)
C5—C4—H4A	120.7	C12—C11—H11A	120.1
C3—C4—H4A	120.7	C10—C11—H11A	120.1
C4—C5—C6	121.3 (4)	F1—C12—C13	119.5 (4)
C4—C5—H5A	119.4	F1—C12—C11	119.2 (5)
C6—C5—H5A	119.4	C13—C12—C11	121.3 (4)
C5—C6—C1	118.6 (4)	C12—C13—C14	120.4 (4)
C5—C6—C7	120.5 (4)	C12—C13—Cl1	119.4 (3)
C1—C6—C7	120.9 (4)	C14—C13—Cl1	120.2 (4)
C6—C7—C8	113.1 (3)	C13—C14—C9	118.7 (4)
C6—C7—H7A	109.0	C13—C14—H14A	120.6
C8—C7—H7A	109.0	C9—C14—H14A	120.6

C6—C1—C2—C3	−0.7 (6)	C8—N1—C9—C10	−41.6 (6)
C1—C2—C3—C4	1.1 (6)	C8—N1—C9—C14	141.6 (4)
C1—C2—C3—Br1	−178.0 (3)	C14—C9—C10—C11	−0.7 (7)
C2—C3—C4—C5	−1.2 (6)	N1—C9—C10—C11	−177.4 (4)
Br1—C3—C4—C5	177.8 (3)	C9—C10—C11—C12	1.5 (8)
C3—C4—C5—C6	1.1 (6)	C10—C11—C12—F1	179.8 (5)
C4—C5—C6—C1	−0.7 (6)	C10—C11—C12—C13	−1.4 (8)
C4—C5—C6—C7	−179.3 (4)	F1—C12—C13—C14	179.3 (4)
C2—C1—C6—C5	0.5 (6)	C11—C12—C13—C14	0.5 (8)
C2—C1—C6—C7	179.1 (4)	F1—C12—C13—Cl1	−0.8 (6)
C5—C6—C7—C8	−95.2 (5)	C11—C12—C13—Cl1	−179.6 (4)
C1—C6—C7—C8	86.3 (5)	C12—C13—C14—C9	0.2 (7)
C9—N1—C8—O1	−2.9 (6)	Cl1—C13—C14—C9	−179.6 (3)
C9—N1—C8—C7	179.2 (4)	C10—C9—C14—C13	−0.1 (6)
C6—C7—C8—O1	8.2 (6)	N1—C9—C14—C13	176.7 (4)
C6—C7—C8—N1	−174.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.88	1.97	2.844 (5)	172
C2—H2A···O1ⁱⁱ	0.95	2.58	3.321 (5)	135
C10—H10A···Cl1ⁱⁱⁱ	0.95	2.67	3.583 (5)	160
C11—H11A···F1^iv	0.95	2.52	3.443 (6)	165

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀BrClFNO
M_r	342.59
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	4.9120 (5), 6.3131 (6), 42.517 (4)
V (Å³)	1318.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.32
Crystal size (mm)	0.30 × 0.17 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.440, 0.806
No. of measured, independent and observed [I > 2σ(I)] reflections	10866, 4737, 4358
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.120, 1.15
No. of reflections	4737
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.86, −1.82
Absolute structure	Flack (1983), 1929 Friedel pairs
Absolute structure parameter	0.065 (14)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.8800	1.9700	2.844 (5)	172.00
C2—H2A···O1ⁱⁱ	0.9500	2.5800	3.321 (5)	135.00
C10—H10A···Cl1ⁱⁱⁱ	0.9500	2.6700	3.583 (5)	160.00
C11—H11A···F1^iv	0.9500	2.5200	3.443 (6)	165.00

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors would like to thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). BN also thanks the UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP–DRS-Phase 1 programme.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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