2-(4-Bromo-phen-yl)-N-(3-chloro-4-fluoro-phen-yl)acetamide.

In the title compound, C(14)H(10)BrClFNO, the benzene rings form a dihedral angle of 64.0 (2)°. In the crystal, mol-ecules are linked via inter-molecular 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 = 342.59

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.120

S = 1.15

4737 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −1.82 e Å−3

Absolute structure: Flack (1983 ▶), 1929 Friedel pairs

Flack parameter: 0.065 (14)

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032977/rz2791sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032977/rz2791Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032977/rz2791Isup3.cml

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

C14H10BrClFNO	F(000) = 680
Mr = 342.59	Dx = 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

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	Rint = 0.032
φ and ω scans	θmax = 32.5°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
Tmin = 0.440, Tmax = 0.806	k = −9→9
10866 measured reflections	l = −46→63

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(Fo2) + (0.0038P)2 + 3.9457P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max = 0.001
4737 reflections	Δρmax = 0.86 e Å−3
173 parameters	Δρmin = −1.82 e Å−3
0 restraints	Absolute structure: Flack (1983), 1929 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.065 (14)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···F1iv	0.95	2.52	3.443 (6)	165

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⋯F1iv	0.95	2.52	3.443 (6)	165

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .