N-(4-Bromo-phen-yl)-2-(naphthalen-1-yl)acetamide.

In the title compound, C(18)H(14)BrNO, the naphthalene ring system and the benzene ring form dihedral angles of 78.8 (2) and 19.7 (2)°, respectively, with the acetamide C-C(=O)-N plane. The naphthalene ring system forms a dihedral angle of 64.88 (19)° with the benzene ring. In the crystal, mol-ecules are linked via inter-molecular bifurcated (N,C)-H⋯O hydrogen bonds, generating an R(2) (1)(6) ring motif, forming chains along the b axis.

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 studies of amides in therapy, myocardial infarction and ischemic disease, see: Dorsch et al. (2002 ▶); Wang, Li & Li (2010 ▶); Wang, Beck et al. (2010 ▶). For related structures, see: Fun et al. (2010 ▶); Li & Wu (2010 ▶); Xiao et al. (2010 ▶); Praveen et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the definition of graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H14BrNO

M = 340.21

Orthorhombic,

a = 12.6837 (11) Å

b = 9.4047 (11) Å

c = 25.641 (3) Å

V = 3058.6 (6) Å3

Z = 8

Mo Kα radiation

μ = 2.69 mm−1

T = 296 K

0.40 × 0.30 × 0.28 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.415, T max = 0.523

18691 measured reflections

2999 independent reflections

1864 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.182

S = 1.02

2999 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.53 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/S1600536811041110/is2786sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041110/is2786Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041110/is2786Isup3.cml

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

C18H14BrNO	F(000) = 1376
Mr = 340.21	Dx = 1.478 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3596 reflections
a = 12.6837 (11) Å	θ = 2.3–21.0°
b = 9.4047 (11) Å	µ = 2.69 mm−1
c = 25.641 (3) Å	T = 296 K
V = 3058.6 (6) Å3	Block, colourless
Z = 8	0.40 × 0.30 × 0.28 mm

Bruker SMART APEXII DUO CCD area-detector diffractometer	2999 independent reflections
Radiation source: fine-focus sealed tube	1864 reflections with I > 2σ(I)
graphite	Rint = 0.046
φ and ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.415, Tmax = 0.523	k = −11→11
18691 measured reflections	l = −29→31

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.081P)2 + 1.7994P] where P = (Fo2 + 2Fc2)/3
2999 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.53 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	0.68647 (5)	0.59626 (9)	0.26162 (3)	0.1354 (4)
O1	0.2893 (2)	0.3465 (2)	0.09635 (13)	0.0798 (8)
N1	0.3185 (2)	0.5799 (3)	0.11054 (13)	0.0606 (7)
H1N1	0.2943	0.6557	0.1026	0.073*
C1	0.0129 (3)	0.4200 (4)	0.07382 (18)	0.0776 (11)
C2	0.0061 (4)	0.5306 (5)	0.11333 (19)	0.0917 (13)
H2A	0.0608	0.5956	0.1175	0.110*
C3	−0.0795 (5)	0.5381 (7)	0.1437 (2)	0.1183 (18)
H3A	−0.0837	0.6095	0.1687	0.142*
C4	−0.1616 (5)	0.4428 (8)	0.1390 (3)	0.1343 (16)
H4A	−0.2200	0.4522	0.1606	0.161*
C5	−0.1592 (5)	0.3370 (9)	0.1039 (3)	0.1343 (16)
H5A	−0.2151	0.2734	0.1015	0.161*
C6	−0.0718 (3)	0.3231 (5)	0.07082 (19)	0.0889 (13)
C7	−0.0643 (5)	0.2134 (6)	0.0329 (3)	0.1152 (19)
H7A	−0.1179	0.1463	0.0306	0.138*
C8	0.0194 (6)	0.2039 (6)	−0.0004 (2)	0.1104 (17)
H8A	0.0219	0.1337	−0.0260	0.133*
C9	0.1015 (4)	0.3026 (4)	0.00486 (18)	0.0880 (12)
H9A	0.1595	0.2944	−0.0171	0.106*
C10	0.1007 (3)	0.4098 (4)	0.04051 (16)	0.0719 (10)
C11	0.1911 (3)	0.5111 (4)	0.04556 (17)	0.0749 (10)
H11A	0.1636	0.6049	0.0534	0.090*
H11B	0.2272	0.5167	0.0123	0.090*
C12	0.2695 (3)	0.4708 (3)	0.08686 (15)	0.0604 (8)
C13	0.4021 (3)	0.5751 (3)	0.14681 (13)	0.0573 (8)
C14	0.4212 (3)	0.6974 (4)	0.17541 (16)	0.0740 (10)
H14A	0.3773	0.7759	0.1716	0.089*
C15	0.5052 (4)	0.7029 (5)	0.20955 (17)	0.0906 (13)
H15A	0.5180	0.7851	0.2287	0.109*
C16	0.5701 (3)	0.5868 (5)	0.21535 (18)	0.0838 (12)
C17	0.5511 (3)	0.4651 (5)	0.18744 (18)	0.0819 (11)
H17A	0.5950	0.3866	0.1915	0.098*
C18	0.4673 (3)	0.4587 (4)	0.15334 (16)	0.0707 (10)
H18A	0.4545	0.3758	0.1346	0.085*

	U11	U22	U33	U12	U13	U23
Br1	0.1139 (5)	0.1942 (8)	0.0981 (5)	−0.0291 (4)	−0.0306 (3)	−0.0162 (4)
O1	0.0801 (16)	0.0393 (12)	0.120 (2)	−0.0026 (10)	−0.0274 (15)	0.0069 (13)
N1	0.0672 (16)	0.0380 (12)	0.077 (2)	−0.0013 (11)	0.0057 (14)	0.0018 (13)
C1	0.069 (2)	0.082 (3)	0.082 (3)	0.0096 (19)	−0.017 (2)	0.011 (2)
C2	0.089 (3)	0.090 (3)	0.096 (3)	0.015 (2)	−0.002 (3)	−0.005 (3)
C3	0.112 (4)	0.123 (4)	0.120 (4)	0.025 (3)	0.013 (3)	−0.014 (4)
C4	0.087 (2)	0.174 (5)	0.143 (4)	−0.001 (3)	−0.005 (3)	0.002 (3)
C5	0.087 (2)	0.174 (5)	0.143 (4)	−0.001 (3)	−0.005 (3)	0.002 (3)
C6	0.079 (3)	0.088 (3)	0.100 (3)	−0.006 (2)	−0.035 (2)	0.013 (3)
C7	0.110 (4)	0.099 (4)	0.137 (5)	−0.015 (3)	−0.061 (4)	0.005 (4)
C8	0.136 (5)	0.088 (3)	0.107 (4)	0.014 (3)	−0.048 (4)	−0.014 (3)
C9	0.113 (3)	0.070 (2)	0.081 (3)	0.011 (2)	−0.027 (2)	−0.005 (2)
C10	0.082 (2)	0.064 (2)	0.070 (2)	0.0090 (18)	−0.018 (2)	0.013 (2)
C11	0.085 (2)	0.057 (2)	0.082 (3)	−0.0006 (17)	−0.005 (2)	0.011 (2)
C12	0.0600 (18)	0.0450 (17)	0.076 (2)	−0.0011 (14)	0.0071 (16)	0.0031 (17)
C13	0.0647 (18)	0.0478 (16)	0.059 (2)	−0.0103 (14)	0.0104 (16)	0.0009 (15)
C14	0.090 (3)	0.061 (2)	0.071 (2)	−0.0100 (18)	0.014 (2)	−0.0094 (19)
C15	0.108 (3)	0.091 (3)	0.073 (3)	−0.027 (3)	0.013 (2)	−0.024 (2)
C16	0.078 (3)	0.106 (3)	0.068 (3)	−0.019 (2)	0.002 (2)	−0.003 (2)
C17	0.072 (2)	0.081 (2)	0.093 (3)	−0.0039 (19)	−0.003 (2)	0.003 (2)
C18	0.072 (2)	0.0562 (18)	0.084 (3)	−0.0029 (16)	−0.0043 (19)	−0.0047 (19)

Br1—C16	1.896 (4)	C8—C9	1.402 (8)
O1—C12	1.220 (4)	C8—H8A	0.9300
N1—C12	1.345 (4)	C9—C10	1.361 (6)
N1—C13	1.410 (5)	C9—H9A	0.9300
N1—H1N1	0.8031	C10—C11	1.496 (5)
C1—C10	1.407 (6)	C11—C12	1.501 (5)
C1—C6	1.411 (6)	C11—H11A	0.9700
C1—C2	1.455 (6)	C11—H11B	0.9700
C2—C3	1.337 (7)	C13—C18	1.382 (5)
C2—H2A	0.9300	C13—C14	1.385 (5)
C3—C4	1.379 (8)	C14—C15	1.380 (6)
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.342 (10)	C15—C16	1.374 (7)
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.401 (8)	C16—C17	1.371 (6)
C5—H5A	0.9300	C17—C18	1.378 (6)
C6—C7	1.421 (8)	C17—H17A	0.9300
C7—C8	1.366 (8)	C18—H18A	0.9300
C7—H7A	0.9300
C12—N1—C13	128.4 (3)	C9—C10—C1	117.7 (4)
C12—N1—H1N1	112.7	C9—C10—C11	121.6 (4)
C13—N1—H1N1	119.0	C1—C10—C11	120.7 (4)
C10—C1—C6	121.7 (4)	C10—C11—C12	114.1 (3)
C10—C1—C2	121.2 (4)	C10—C11—H11A	108.7
C6—C1—C2	117.1 (4)	C12—C11—H11A	108.7
C3—C2—C1	119.4 (5)	C10—C11—H11B	108.7
C3—C2—H2A	120.3	C12—C11—H11B	108.7
C1—C2—H2A	120.3	H11A—C11—H11B	107.6
C2—C3—C4	121.9 (6)	O1—C12—N1	123.1 (3)
C2—C3—H3A	119.1	O1—C12—C11	121.3 (3)
C4—C3—H3A	119.1	N1—C12—C11	115.6 (3)
C5—C4—C3	121.5 (7)	C18—C13—C14	119.2 (4)
C5—C4—H4A	119.2	C18—C13—N1	123.7 (3)
C3—C4—H4A	119.2	C14—C13—N1	117.0 (3)
C4—C5—C6	119.5 (6)	C15—C14—C13	120.1 (4)
C4—C5—H5A	120.2	C15—C14—H14A	119.9
C6—C5—H5A	120.2	C13—C14—H14A	119.9
C5—C6—C1	120.6 (5)	C16—C15—C14	120.1 (4)
C5—C6—C7	122.4 (5)	C16—C15—H15A	120.0
C1—C6—C7	117.1 (5)	C14—C15—H15A	120.0
C8—C7—C6	121.9 (5)	C17—C16—C15	120.1 (4)
C8—C7—H7A	119.1	C17—C16—Br1	120.1 (4)
C6—C7—H7A	119.1	C15—C16—Br1	119.8 (3)
C7—C8—C9	118.3 (5)	C16—C17—C18	120.2 (4)
C7—C8—H8A	120.9	C16—C17—H17A	119.9
C9—C8—H8A	120.9	C18—C17—H17A	119.9
C10—C9—C8	123.4 (6)	C17—C18—C13	120.3 (4)
C10—C9—H9A	118.3	C17—C18—H18A	119.9
C8—C9—H9A	118.3	C13—C18—H18A	119.9
C10—C1—C2—C3	178.9 (4)	C2—C1—C10—C11	1.3 (5)
C6—C1—C2—C3	−1.7 (6)	C9—C10—C11—C12	−95.0 (4)
C1—C2—C3—C4	0.6 (8)	C1—C10—C11—C12	83.0 (4)
C2—C3—C4—C5	0.6 (11)	C13—N1—C12—O1	3.8 (6)
C3—C4—C5—C6	−0.5 (11)	C13—N1—C12—C11	−173.5 (3)
C4—C5—C6—C1	−0.6 (9)	C10—C11—C12—O1	34.1 (5)
C4—C5—C6—C7	180.0 (6)	C10—C11—C12—N1	−148.6 (3)
C10—C1—C6—C5	−178.9 (5)	C12—N1—C13—C18	18.9 (5)
C2—C1—C6—C5	1.7 (6)	C12—N1—C13—C14	−164.0 (3)
C10—C1—C6—C7	0.5 (6)	C18—C13—C14—C15	0.7 (5)
C2—C1—C6—C7	−178.9 (4)	N1—C13—C14—C15	−176.5 (3)
C5—C6—C7—C8	177.6 (5)	C13—C14—C15—C16	−0.1 (6)
C1—C6—C7—C8	−1.9 (7)	C14—C15—C16—C17	−0.3 (6)
C6—C7—C8—C9	2.5 (8)	C14—C15—C16—Br1	179.1 (3)
C7—C8—C9—C10	−1.9 (7)	C15—C16—C17—C18	0.2 (7)
C8—C9—C10—C1	0.6 (6)	Br1—C16—C17—C18	−179.2 (3)
C8—C9—C10—C11	178.7 (4)	C16—C17—C18—C13	0.4 (6)
C6—C1—C10—C9	0.0 (5)	C14—C13—C18—C17	−0.8 (6)
C2—C1—C10—C9	179.4 (4)	N1—C13—C18—C17	176.2 (4)
C6—C1—C10—C11	−178.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.80	2.09	2.879 (3)	167
C11—H11A···O1i	0.97	2.59	3.422 (4)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.80	2.09	2.879 (3)	167
C11—H11A⋯O1i	0.97	2.59	3.422 (4)	143

Symmetry code: (i) .