2-(4-Bromo­phen­yl)-N-(2-methoxy­phen­yl)acetamide

Xiao, Z.-P.; Ouyang, Y.-Z.; Qin, S.-D.; Xie, T.; Yang, J.

doi:10.1107/S1600536809051812

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o67

doi:10.1107/S1600536809051812

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2-(4-Bromophenyl)-N-(2-methoxyphenyl)acetamide

Zhu-Ping Xiao,^a ^* Yu-Zhu Ouyang,^a Shi-Dong Qin,^a Tian Xie ^a and Jia Yang ^a

^aCollege of Chemistry & Chemical Engineering, Jishou University, Jishou 416000, People's Republic of China
^*Correspondence e-mail: xiaozhuping2005@163.com

(Received 1 December 2009; accepted 1 December 2009; online 9 December 2009)

In the title compound, C₁₅H₁₄BrNO₂, the 4-bromophenyl 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, intermolecular N—H⋯O hydrogen bonds and C—H⋯π contacts connect the molecules, 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_r = 320.18
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.133
S = 1.01
2642 reflections
177 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.62 e Å⁻³

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) x+1, y, z. Cg1 is the centroid of the C9–C14 ring.

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.

Supporting information

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

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

checkCIF report

Comment top

N-Substituted 2-phenylacetamides are very interesting compounds because of their structural similarity to the lateral chain of natural benzylpenicillin (Mijin et al., 2008; Mijin et al., 2006). As part of our work involving the synthesis of a series of phenylacetamide derivatives for antimicrobial activity screening, we report herein the crystal structure of the title phenylacetamide derivative (I).

The molecular structure of the title compound is shown in Fig. 1. The two benzene rings in form a dihedral angle of 50.88 (14) °. The acetamide fragment makes a dihedral angle of 76.55 (17) ° with the p-bromophenyl group [Br1/C1-C6]. The two benzene rings and the acetamide skeleton show a W-shape figuration. In the crystal structure, intermolecular N—H···O together with C—H···π contacts connect molecules to form an infinite line running along the crystallographic a-axis direction (see Fig. 2).

Related literature top

For background to phenylacetamide derivatives as potential antimicrobial agents, see: Mijin & Marinković (2006); Mijin et al. (2008). Cg1 is the centroid of the C9–C14 ring.

Experimental top

1.17 g (5 mmol) of 4-bromophenylacetyl chloride and 0.62 g (5 mmol) of 2-methoxyaniline were dissolved into 20 mL of fresh distilled CH₂Cl₂. The mixture was stirred in the present of triethylamine at 273 K for about 3 h. The contents were poured into 100 ml of ice-cold aqueous hydrochloride acid (w % = 5%) with stirring, which was extracted thrice with EtOAc. The EtOAc solution was washed with aqueous saturated NaHCO₃ and brine, dried and concentrated under reduced pressure to give the product as a light yellow solid which on crystallization from EtOAc-petrolium ether gave colourless blocks of (I).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of (I) with hydrogen bonds indicated by thin dashed lines and C—H···π contacts shown as thick dashed lines.

2-(4-Bromophenyl)-N-(2-methoxyphenyl)acetamide top

Crystal data top

C₁₅H₁₄BrNO₂	Z = 2
M_r = 320.18	F(000) = 324
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0528P)² + 0.5023P] where P = (F_o² + 2F_c²)/3
2642 reflections	(Δ/σ)_max < 0.001
177 parameters	Δρ_max = 0.79 e Å⁻³
0 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

C₁₅H₁₄BrNO₂	γ = 85.18 (3)°
M_r = 320.18	V = 690.5 (10) Å³
Triclinic, P1	Z = 2
a = 4.851 (4) Å	Mo Kα radiation
b = 12.083 (10) Å	µ = 2.97 mm⁻¹
c = 12.265 (10) Å	T = 296 K
α = 74.61 (3)°	0.25 × 0.20 × 0.10 mm
β = 87.47 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	2642 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1441 reflections with I > 2σ(I)
T_min = 0.524, T_max = 0.755	R_int = 0.027
3678 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.79 e Å⁻³
2642 reflections	Δρ_min = −0.62 e Å⁻³
177 parameters

Special details top

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	−0.42219 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄BrNO₂
M_r	320.18
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	4.851 (4), 12.083 (10), 12.265 (10)
α, β, γ (°)	74.61 (3), 87.47 (3), 85.18 (3)
V (Å³)	690.5 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.97
Crystal size (mm)	0.25 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.524, 0.755
No. of measured, independent and observed [I > 2σ(I)] reflections	3678, 2642, 1441
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.133, 1.01
No. of reflections	2642
No. of parameters	177
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.62

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)	137.0

Symmetry code: (i) x+1, y, z.

Acknowledgements

This work was supported by the Scientific Research Fund of Hunan Provincial Education Department, China (grant No. 09B083) and the Key Laboratory of Hunan Forest Products and Chemical Industry Engineering of Hunan Province, China (grant No. JDZ200904).

References

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