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

In the title compound, C(15)H(14)BrNO(2), the 4-bromo-phenyl fragment makes a dihedral angle of 76.55 (17)° with the acetamide unit and the dihedral angle between the two benzene rings is 50.88 (14)°. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds and C-H⋯π contacts connect the mol-ecules, forming chains propagating in [100].

Related literature

For background to phenyl­acetamide derivatives as potential anti­microbial agents, see: Mijin & Marinković (2006 ▶); Mijin et al. (2008 ▶).

Experimental

Crystal data

C15H14BrNO2

M = 320.18

Triclinic,

a = 4.851 (4) Å

b = 12.083 (10) Å

c = 12.265 (10) Å

α = 74.61 (3)°

β = 87.47 (3)°

γ = 85.18 (3)°

V = 690.5 (10) Å3

Z = 2

Mo Kα radiation

μ = 2.97 mm−1

T = 296 K

0.25 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.524, T max = 0.755

3678 measured reflections

2642 independent reflections

1441 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.133

S = 1.01

2642 reflections

177 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.79 e Å−3

Δρmin = −0.62 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051812/hb5263sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051812/hb5263Isup2.hkl

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

C15H14BrNO2	Z = 2
Mr = 320.18	F(000) = 324
Triclinic, P1	Dx = 1.540 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.851 (4) Å	Cell parameters from 1389 reflections
b = 12.083 (10) Å	θ = 2.4–26.0°
c = 12.265 (10) Å	µ = 2.97 mm−1
α = 74.61 (3)°	T = 296 K
β = 87.47 (3)°	Block, colourless
γ = 85.18 (3)°	0.25 × 0.20 × 0.10 mm
V = 690.5 (10) Å3

Bruker SMART APEX CCD diffractometer	2642 independent reflections
Radiation source: fine-focus sealed tube	1441 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scan	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.524, Tmax = 0.755	k = −10→14
3678 measured reflections	l = −14→15

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0528P)2 + 0.5023P] where P = (Fo2 + 2Fc2)/3
2642 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.79 e Å−3
0 restraints	Δρmin = −0.61 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	−0.42219 (14)	0.65388 (5)	0.56611 (5)	0.0755 (3)
C1	0.2053 (9)	0.4363 (4)	0.8358 (4)	0.0410 (12)
C2	0.0778 (11)	0.5420 (4)	0.8452 (4)	0.0501 (14)
H2	0.1226	0.5707	0.9049	0.060*
C3	−0.1146 (11)	0.6050 (4)	0.7670 (4)	0.0519 (14)
H3	−0.2009	0.6741	0.7753	0.062*
C4	−0.1743 (10)	0.5640 (4)	0.6782 (4)	0.0469 (13)
C5	−0.0535 (11)	0.4593 (4)	0.6656 (4)	0.0515 (14)
H5	−0.0979	0.4315	0.6052	0.062*
C6	0.1339 (10)	0.3977 (4)	0.7450 (4)	0.0493 (14)
H6	0.2152	0.3277	0.7371	0.059*
C7	0.4103 (10)	0.3672 (4)	0.9209 (4)	0.0525 (14)
H7A	0.4654	0.4153	0.9669	0.063*
H7B	0.5741	0.3452	0.8811	0.063*
C8	0.2970 (10)	0.2594 (4)	0.9980 (4)	0.0394 (12)
C9	0.4355 (9)	0.0797 (4)	1.1414 (4)	0.0393 (12)
C10	0.5674 (10)	0.0471 (4)	1.2445 (4)	0.0429 (12)
C11	0.5351 (11)	−0.0618 (4)	1.3177 (4)	0.0543 (15)
H11	0.6274	−0.0846	1.3858	0.065*
C12	0.3679 (12)	−0.1345 (4)	1.2889 (5)	0.0589 (15)
H12	0.3461	−0.2064	1.3383	0.071*
C13	0.2316 (12)	−0.1032 (4)	1.1884 (5)	0.0581 (15)
H13	0.1152	−0.1530	1.1708	0.070*
C14	0.2681 (10)	0.0036 (4)	1.1129 (4)	0.0465 (13)
H14	0.1811	0.0240	1.0436	0.056*
C15	0.8674 (12)	0.0996 (5)	1.3693 (5)	0.0636 (16)
H15A	0.7386	0.0774	1.4315	0.095*
H15B	0.9569	0.1654	1.3758	0.095*
H15C	1.0038	0.0369	1.3706	0.095*
H1	0.645 (11)	0.205 (4)	1.063 (4)	0.055 (17)*
N1	0.4851 (9)	0.1880 (3)	1.0651 (3)	0.0432 (11)
O1	0.7238 (7)	0.1276 (3)	1.2659 (3)	0.0558 (10)
O2	0.0524 (7)	0.2422 (3)	0.9995 (3)	0.0567 (10)

	U11	U22	U33	U12	U13	U23
Br1	0.0798 (5)	0.0708 (4)	0.0623 (4)	0.0148 (3)	−0.0253 (3)	0.0037 (3)
C1	0.033 (3)	0.035 (3)	0.050 (3)	−0.009 (2)	−0.005 (2)	0.000 (2)
C2	0.061 (4)	0.039 (3)	0.046 (3)	−0.009 (3)	−0.006 (3)	−0.003 (2)
C3	0.064 (4)	0.035 (3)	0.053 (3)	0.006 (3)	−0.004 (3)	−0.008 (2)
C4	0.048 (3)	0.043 (3)	0.041 (3)	−0.001 (2)	−0.003 (2)	0.004 (2)
C5	0.062 (4)	0.043 (3)	0.050 (3)	−0.005 (3)	−0.007 (3)	−0.011 (2)
C6	0.049 (3)	0.035 (3)	0.059 (4)	0.000 (2)	0.003 (3)	−0.007 (2)
C7	0.036 (3)	0.047 (3)	0.065 (4)	−0.014 (2)	−0.015 (3)	0.008 (3)
C8	0.033 (3)	0.040 (3)	0.042 (3)	−0.006 (2)	−0.004 (2)	−0.005 (2)
C9	0.034 (3)	0.037 (3)	0.043 (3)	−0.005 (2)	0.002 (2)	−0.004 (2)
C10	0.042 (3)	0.035 (3)	0.049 (3)	0.000 (2)	−0.004 (2)	−0.008 (2)
C11	0.062 (4)	0.049 (3)	0.044 (3)	0.008 (3)	−0.004 (3)	−0.001 (3)
C12	0.063 (4)	0.033 (3)	0.069 (4)	−0.002 (3)	0.003 (3)	0.004 (3)
C13	0.061 (4)	0.037 (3)	0.078 (4)	−0.012 (3)	0.000 (3)	−0.015 (3)
C14	0.047 (3)	0.043 (3)	0.048 (3)	−0.009 (2)	−0.005 (3)	−0.008 (2)
C15	0.065 (4)	0.068 (4)	0.058 (4)	−0.001 (3)	−0.018 (3)	−0.015 (3)
N1	0.031 (3)	0.038 (2)	0.053 (3)	−0.011 (2)	−0.010 (2)	0.0044 (19)
O1	0.061 (2)	0.054 (2)	0.049 (2)	−0.0071 (18)	−0.0191 (18)	−0.0043 (17)
O2	0.029 (2)	0.056 (2)	0.072 (3)	−0.0111 (17)	−0.0083 (17)	0.0096 (18)

Br1—C4	1.910 (5)	C9—C10	1.388 (7)
C1—C6	1.383 (7)	C9—C14	1.397 (7)
C1—C2	1.403 (7)	C9—N1	1.424 (6)
C1—C7	1.505 (6)	C10—O1	1.367 (6)
C2—C3	1.394 (7)	C10—C11	1.399 (7)
C2—H2	0.9300	C11—C12	1.365 (8)
C3—C4	1.361 (7)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.372 (7)
C4—C5	1.393 (7)	C12—H12	0.9300
C5—C6	1.381 (7)	C13—C14	1.394 (7)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.521 (6)	C15—O1	1.421 (6)
C7—H7A	0.9700	C15—H15A	0.9600
C7—H7B	0.9700	C15—H15B	0.9600
C8—O2	1.220 (5)	C15—H15C	0.9600
C8—N1	1.346 (6)	N1—H1	0.81 (5)
C6—C1—C2	117.2 (4)	C10—C9—N1	119.0 (4)
C6—C1—C7	121.3 (5)	C14—C9—N1	121.6 (4)
C2—C1—C7	121.6 (5)	O1—C10—C9	115.3 (4)
C3—C2—C1	121.4 (5)	O1—C10—C11	124.8 (5)
C3—C2—H2	119.3	C9—C10—C11	119.9 (5)
C1—C2—H2	119.3	C12—C11—C10	119.9 (5)
C4—C3—C2	119.0 (5)	C12—C11—H11	120.1
C4—C3—H3	120.5	C10—C11—H11	120.1
C2—C3—H3	120.5	C11—C12—C13	121.1 (5)
C3—C4—C5	121.6 (5)	C11—C12—H12	119.4
C3—C4—Br1	119.3 (4)	C13—C12—H12	119.4
C5—C4—Br1	119.1 (4)	C12—C13—C14	119.8 (5)
C6—C5—C4	118.3 (5)	C12—C13—H13	120.1
C6—C5—H5	120.9	C14—C13—H13	120.1
C4—C5—H5	120.9	C13—C14—C9	119.9 (5)
C5—C6—C1	122.5 (5)	C13—C14—H14	120.0
C5—C6—H6	118.7	C9—C14—H14	120.0
C1—C6—H6	118.7	O1—C15—H15A	109.5
C1—C7—C8	113.2 (4)	O1—C15—H15B	109.5
C1—C7—H7A	108.9	H15A—C15—H15B	109.5
C8—C7—H7A	108.9	O1—C15—H15C	109.5
C1—C7—H7B	108.9	H15A—C15—H15C	109.5
C8—C7—H7B	108.9	H15B—C15—H15C	109.5
H7A—C7—H7B	107.7	C8—N1—C9	126.0 (4)
O2—C8—N1	123.6 (4)	C8—N1—H1	120 (4)
O2—C8—C7	121.6 (4)	C9—N1—H1	114 (4)
N1—C8—C7	114.8 (4)	C10—O1—C15	118.3 (4)
C10—C9—C14	119.3 (4)
C6—C1—C2—C3	0.6 (7)	C14—C9—C10—C11	0.9 (7)
C7—C1—C2—C3	−179.2 (4)	N1—C9—C10—C11	−176.1 (4)
C1—C2—C3—C4	−1.6 (7)	O1—C10—C11—C12	178.4 (5)
C2—C3—C4—C5	1.8 (8)	C9—C10—C11—C12	−1.8 (8)
C2—C3—C4—Br1	−176.6 (4)	C10—C11—C12—C13	0.6 (8)
C3—C4—C5—C6	−1.0 (8)	C11—C12—C13—C14	1.4 (8)
Br1—C4—C5—C6	177.4 (4)	C12—C13—C14—C9	−2.2 (8)
C4—C5—C6—C1	−0.1 (7)	C10—C9—C14—C13	1.0 (7)
C2—C1—C6—C5	0.2 (7)	N1—C9—C14—C13	178.0 (5)
C7—C1—C6—C5	180.0 (4)	O2—C8—N1—C9	4.5 (8)
C6—C1—C7—C8	−71.8 (6)	C7—C8—N1—C9	−177.4 (5)
C2—C1—C7—C8	107.9 (5)	C10—C9—N1—C8	−142.9 (5)
C1—C7—C8—O2	−10.1 (7)	C14—C9—N1—C8	40.2 (7)
C1—C7—C8—N1	171.8 (4)	C9—C10—O1—C15	−179.3 (4)
C14—C9—C10—O1	−179.2 (4)	C11—C10—O1—C15	0.6 (7)
N1—C9—C10—O1	3.8 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.81 (5)	2.13 (5)	2.912 (6)	160 (5)
C15—H15C···Cg1i	0.96	2.86	3.617 (7)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.81 (5)	2.13 (5)	2.912 (6)	160 (5)
C15—H15C⋯Cg1i	0.96	2.86	3.617 (7)	137

Symmetry code: (i) . Cg1 is the centroid of the C9–C14 ring.