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

The title compound, C(14)H(11)BrClNO, consists of chloro-benzene and bromo-benzene units which are linked at either end of the N-methyl-propionamide group. The chloro-benzene unit [maximum deviation = 0.005 (4) Å] makes a dihedral angle of 68.21 (19)° with the bromo-benzene unit [maximum deviation = 0.012 (3) Å]. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into chains along [010].

Related literature

For the structural similarity of N-substituted 2-aryl­acetamides to the lateral chain of natural benzyl­penicillin, see: Mijin & Marinkovic (2006 ▶); Mijin et al. (2008 ▶). For the coordination abilities of amides, see: Wu et al. (2008 ▶, 2010 ▶). For related structures, see: Praveen et al. (2011a ▶,b ▶,c ▶); Fun et al. (2011a ▶,b ▶).

Experimental

Crystal data

C14H11BrClNO

M = 324.60

Monoclinic,

a = 15.584 (8) Å

b = 4.763 (3) Å

c = 18.139 (10) Å

β = 96.984 (11)°

V = 1336.5 (12) Å3

Z = 4

Mo Kα radiation

μ = 3.26 mm−1

T = 296 K

0.69 × 0.19 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.211, T max = 0.826

12836 measured reflections

3880 independent reflections

1970 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.166

S = 1.03

3880 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.54 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812002383/tk5050sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002383/tk5050Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002383/tk5050Isup3.cml

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

C14H11BrClNO	F(000) = 648
Mr = 324.60	Dx = 1.613 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1975 reflections
a = 15.584 (8) Å	θ = 2.5–24.6°
b = 4.763 (3) Å	µ = 3.26 mm−1
c = 18.139 (10) Å	T = 296 K
β = 96.984 (11)°	Plate, colourless
V = 1336.5 (12) Å3	0.69 × 0.19 × 0.06 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3880 independent reflections
Radiation source: fine-focus sealed tube	1970 reflections with I > 2σ(I)
graphite	Rint = 0.076
φ and ω scans	θmax = 30.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→21
Tmin = 0.211, Tmax = 0.826	k = −6→6
12836 measured reflections	l = −25→24

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.P)2 + 0.5271P] where P = (Fo2 + 2Fc2)/3
3880 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

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	0.28762 (3)	0.70007 (12)	0.35364 (3)	0.0891 (3)
O1	−0.1362 (2)	0.6167 (5)	0.3893 (3)	0.1018 (14)
N1	−0.0827 (2)	1.0487 (6)	0.37965 (19)	0.0562 (9)
Cl1	−0.52585 (7)	0.1650 (2)	0.38444 (7)	0.0663 (3)
C1	0.0462 (3)	0.7777 (7)	0.4237 (2)	0.0594 (10)
H1A	0.0171	0.6980	0.4604	0.071*
C2	0.1300 (3)	0.7001 (8)	0.4179 (2)	0.0607 (10)
H2A	0.1574	0.5677	0.4504	0.073*
C3	0.1732 (3)	0.8182 (8)	0.3642 (2)	0.0573 (9)
C4	0.1331 (3)	1.0177 (8)	0.3172 (2)	0.0667 (11)
H4A	0.1627	1.1011	0.2814	0.080*
C5	0.0495 (3)	1.0933 (8)	0.3232 (3)	0.0652 (11)
H5A	0.0226	1.2285	0.2914	0.078*
C6	0.0047 (2)	0.9718 (6)	0.3758 (2)	0.0471 (8)
C7	−0.1479 (3)	0.8708 (6)	0.3853 (2)	0.0597 (10)
C8	−0.2359 (3)	1.0010 (7)	0.3854 (3)	0.0756 (14)
H8A	−0.2475	1.1210	0.3421	0.091*
H8B	−0.2354	1.1186	0.4291	0.091*
C9	−0.3081 (3)	0.7905 (7)	0.3849 (3)	0.0626 (12)
C10	−0.3510 (3)	0.6898 (7)	0.3188 (3)	0.0634 (11)
H10A	−0.3350	0.7532	0.2740	0.076*
C11	−0.4175 (3)	0.4957 (7)	0.3185 (2)	0.0578 (9)
H11A	−0.4465	0.4305	0.2739	0.069*
C12	−0.4396 (2)	0.4024 (7)	0.3850 (2)	0.0491 (9)
C13	−0.3986 (3)	0.4935 (8)	0.4515 (2)	0.0577 (9)
H13A	−0.4145	0.4264	0.4960	0.069*
C14	−0.3332 (3)	0.6879 (8)	0.4508 (3)	0.0625 (11)
H14A	−0.3049	0.7522	0.4957	0.075*
H1N1	−0.087 (3)	1.197 (8)	0.376 (2)	0.058 (12)*

	U11	U22	U33	U12	U13	U23
Br1	0.0498 (3)	0.1141 (5)	0.1047 (5)	0.0028 (2)	0.0147 (3)	−0.0110 (3)
O1	0.0549 (17)	0.0276 (11)	0.223 (4)	0.0063 (11)	0.018 (2)	−0.0026 (17)
N1	0.055 (2)	0.0268 (13)	0.086 (2)	0.0063 (12)	0.0059 (17)	−0.0021 (13)
Cl1	0.0496 (6)	0.0703 (6)	0.0804 (8)	−0.0048 (4)	0.0137 (5)	−0.0103 (5)
C1	0.059 (2)	0.0541 (19)	0.067 (3)	0.0103 (16)	0.011 (2)	0.0114 (17)
C2	0.057 (2)	0.060 (2)	0.065 (3)	0.0104 (17)	0.004 (2)	0.0087 (18)
C3	0.048 (2)	0.058 (2)	0.065 (3)	−0.0049 (16)	0.005 (2)	−0.0097 (18)
C4	0.062 (3)	0.073 (2)	0.066 (3)	−0.014 (2)	0.013 (2)	0.012 (2)
C5	0.064 (3)	0.0519 (19)	0.076 (3)	−0.0053 (18)	−0.004 (2)	0.0184 (18)
C6	0.0466 (19)	0.0307 (14)	0.063 (2)	0.0002 (13)	0.0010 (17)	−0.0045 (14)
C7	0.055 (2)	0.0294 (14)	0.094 (3)	0.0085 (14)	0.006 (2)	−0.0064 (16)
C8	0.052 (2)	0.0350 (16)	0.140 (4)	0.0064 (15)	0.011 (3)	−0.009 (2)
C9	0.047 (2)	0.0377 (16)	0.102 (4)	0.0123 (14)	0.006 (2)	−0.0054 (18)
C10	0.070 (3)	0.0524 (19)	0.069 (3)	0.0048 (18)	0.010 (2)	0.0058 (18)
C11	0.058 (2)	0.057 (2)	0.058 (2)	0.0030 (17)	0.0024 (19)	−0.0067 (17)
C12	0.0416 (19)	0.0458 (17)	0.060 (2)	0.0098 (14)	0.0067 (18)	−0.0048 (15)
C13	0.050 (2)	0.068 (2)	0.054 (2)	0.0101 (17)	0.0044 (18)	−0.0076 (18)
C14	0.055 (2)	0.060 (2)	0.070 (3)	0.0101 (18)	−0.003 (2)	−0.0201 (19)

Br1—C3	1.902 (4)	C5—H5A	0.9300
O1—C7	1.225 (4)	C7—C8	1.506 (5)
N1—C7	1.337 (5)	C8—C9	1.506 (5)
N1—C6	1.421 (5)	C8—H8A	0.9700
N1—H1N1	0.71 (4)	C8—H8B	0.9700
Cl1—C12	1.756 (4)	C9—C10	1.384 (6)
C1—C2	1.374 (6)	C9—C14	1.391 (6)
C1—C6	1.374 (5)	C10—C11	1.388 (6)
C1—H1A	0.9300	C10—H10A	0.9300
C2—C3	1.370 (6)	C11—C12	1.369 (5)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.376 (6)	C12—C13	1.364 (5)
C4—C5	1.369 (6)	C13—C14	1.379 (6)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.376 (5)	C14—H14A	0.9300
C7—N1—C6	125.6 (3)	C7—C8—C9	113.9 (3)
C7—N1—H1N1	125 (4)	C7—C8—H8A	108.8
C6—N1—H1N1	109 (4)	C9—C8—H8A	108.8
C2—C1—C6	120.7 (4)	C7—C8—H8B	108.8
C2—C1—H1A	119.6	C9—C8—H8B	108.8
C6—C1—H1A	119.6	H8A—C8—H8B	107.7
C3—C2—C1	119.8 (4)	C10—C9—C14	117.7 (4)
C3—C2—H2A	120.1	C10—C9—C8	121.2 (4)
C1—C2—H2A	120.1	C14—C9—C8	121.1 (4)
C2—C3—C4	120.0 (4)	C9—C10—C11	121.1 (4)
C2—C3—Br1	119.9 (3)	C9—C10—H10A	119.4
C4—C3—Br1	120.2 (3)	C11—C10—H10A	119.4
C5—C4—C3	119.8 (4)	C12—C11—C10	118.6 (4)
C5—C4—H4A	120.1	C12—C11—H11A	120.7
C3—C4—H4A	120.1	C10—C11—H11A	120.7
C4—C5—C6	120.8 (4)	C13—C12—C11	122.4 (4)
C4—C5—H5A	119.6	C13—C12—Cl1	119.1 (3)
C6—C5—H5A	119.6	C11—C12—Cl1	118.6 (3)
C1—C6—C5	118.8 (4)	C12—C13—C14	118.2 (4)
C1—C6—N1	121.5 (3)	C12—C13—H13A	120.9
C5—C6—N1	119.7 (3)	C14—C13—H13A	120.9
O1—C7—N1	121.5 (3)	C13—C14—C9	122.0 (4)
O1—C7—C8	122.4 (3)	C13—C14—H14A	119.0
N1—C7—C8	116.1 (3)	C9—C14—H14A	119.0
C6—C1—C2—C3	0.4 (6)	O1—C7—C8—C9	−4.4 (7)
C1—C2—C3—C4	1.2 (6)	N1—C7—C8—C9	174.7 (4)
C1—C2—C3—Br1	−177.5 (3)	C7—C8—C9—C10	−89.3 (5)
C2—C3—C4—C5	−1.4 (6)	C7—C8—C9—C14	89.9 (5)
Br1—C3—C4—C5	177.3 (3)	C14—C9—C10—C11	0.8 (5)
C3—C4—C5—C6	−0.1 (6)	C8—C9—C10—C11	180.0 (3)
C2—C1—C6—C5	−1.8 (6)	C9—C10—C11—C12	−0.7 (5)
C2—C1—C6—N1	178.2 (3)	C10—C11—C12—C13	0.1 (5)
C4—C5—C6—C1	1.7 (6)	C10—C11—C12—Cl1	178.1 (3)
C4—C5—C6—N1	−178.4 (4)	C11—C12—C13—C14	0.4 (5)
C7—N1—C6—C1	−46.6 (6)	Cl1—C12—C13—C14	−177.6 (3)
C7—N1—C6—C5	133.5 (4)	C12—C13—C14—C9	−0.3 (5)
C6—N1—C7—O1	1.5 (7)	C10—C9—C14—C13	−0.3 (5)
C6—N1—C7—C8	−177.6 (4)	C8—C9—C14—C13	−179.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.71 (4)	2.17 (4)	2.843 (4)	160 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.71 (4)	2.17 (4)	2.843 (4)	160 (5)

Symmetry code: (i) .