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

In the title compound, C(18)H(14)ClNO, the naphthalene ring system [maximum deviation = 0.014 (9) Å] forms a dihedral angle of 74.8 (2)° with the benzene ring. In the crystal, mol-ecules are linked via N-H⋯O hydrogen bonds into chains propagating along [010].

Related literature

For general background to and related structures of the title compound, see: Fun et al. (2010 ▶, 2011a ▶,b ▶, 2012 ▶).

Experimental

Crystal data

C18H14ClNO

M = 295.75

Monoclinic,

a = 19.163 (6) Å

b = 5.0458 (11) Å

c = 17.252 (4) Å

β = 116.365 (5)°

V = 1494.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.35 × 0.15 × 0.09 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.916, T max = 0.978

9206 measured reflections

2611 independent reflections

1185 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.208

S = 1.01

2611 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.18 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/S1600536812031613/hb6893sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031613/hb6893Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031613/hb6893Isup3.cml

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

C18H14ClNO	F(000) = 616
Mr = 295.75	Dx = 1.314 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1386 reflections
a = 19.163 (6) Å	θ = 2.4–21.5°
b = 5.0458 (11) Å	µ = 0.25 mm−1
c = 17.252 (4) Å	T = 296 K
β = 116.365 (5)°	Block, colourless
V = 1494.6 (7) Å3	0.35 × 0.15 × 0.09 mm
Z = 4

Bruker SMART APEXII DUO CCD diffractometer	2611 independent reflections
Radiation source: fine-focus sealed tube	1185 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −22→22
Tmin = 0.916, Tmax = 0.978	k = −5→3
9206 measured reflections	l = −20→19

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)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.208	w = 1/[σ2(Fo2) + (0.0913P)2 + 0.5172P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
2611 reflections	Δρmax = 0.32 e Å−3
195 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (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
Cl1	0.30184 (7)	0.9142 (3)	0.11979 (9)	0.1183 (7)
O1	0.64245 (16)	0.5769 (5)	0.1247 (2)	0.0885 (10)
N1	0.6142 (2)	1.0067 (7)	0.1325 (2)	0.0681 (10)
C1	0.8073 (3)	0.5845 (12)	0.0810 (4)	0.1051 (16)
H1A	0.7783	0.6565	0.0263	0.126*
C2	0.8600 (4)	0.3825 (15)	0.0897 (6)	0.130 (2)
H2A	0.8650	0.3194	0.0418	0.156*
C3	0.9041 (4)	0.2791 (13)	0.1703 (7)	0.138 (3)
H3A	0.9402	0.1460	0.1780	0.166*
C4	0.8942 (3)	0.3771 (11)	0.2422 (5)	0.1032 (17)
C5	0.9390 (4)	0.2649 (14)	0.3251 (8)	0.147 (3)
H5A	0.9739	0.1276	0.3328	0.176*
C6	0.9296 (5)	0.363 (2)	0.3916 (7)	0.166 (3)
H6A	0.9598	0.2925	0.4463	0.199*
C8	0.8326 (3)	0.6693 (12)	0.3047 (5)	0.1102 (17)
H8A	0.7972	0.8025	0.2994	0.132*
C7	0.8779 (4)	0.5606 (17)	0.3840 (5)	0.133 (2)
H7A	0.8737	0.6209	0.4326	0.160*
C9	0.8398 (3)	0.5767 (9)	0.2290 (4)	0.0863 (14)
C10	0.7961 (3)	0.6808 (9)	0.1472 (4)	0.0880 (14)
C11	0.7373 (2)	0.9033 (9)	0.1340 (3)	0.0958 (14)
H11A	0.7606	1.0297	0.1810	0.115*
H11B	0.7266	0.9955	0.0806	0.115*
C12	0.6607 (2)	0.8082 (8)	0.1304 (3)	0.0723 (11)
C13	0.5384 (2)	0.9812 (7)	0.1258 (2)	0.0589 (10)
C14	0.4866 (2)	0.7824 (7)	0.0781 (2)	0.0666 (11)
H14A	0.5013	0.6598	0.0479	0.080*
C15	0.4140 (3)	0.7658 (8)	0.0751 (3)	0.0710 (11)
H15A	0.3801	0.6312	0.0436	0.085*
C16	0.3914 (2)	0.9466 (9)	0.1184 (3)	0.0748 (12)
C17	0.4414 (3)	1.1482 (8)	0.1643 (3)	0.0794 (13)
H17A	0.4259	1.2735	0.1931	0.095*
C18	0.5136 (3)	1.1623 (8)	0.1672 (2)	0.0717 (11)
H18B	0.5469	1.2989	0.1982	0.086*
H1N1	0.630 (3)	1.193 (10)	0.140 (3)	0.115 (16)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0979 (10)	0.1515 (14)	0.1228 (12)	0.0188 (9)	0.0646 (9)	0.0142 (10)
O1	0.0811 (19)	0.0456 (17)	0.144 (3)	−0.0048 (15)	0.0547 (19)	−0.0001 (17)
N1	0.077 (2)	0.0456 (19)	0.080 (2)	−0.0074 (18)	0.0337 (19)	0.0019 (17)
C1	0.102 (4)	0.106 (4)	0.128 (5)	−0.025 (3)	0.069 (4)	−0.014 (4)
C2	0.111 (5)	0.121 (5)	0.196 (7)	−0.027 (4)	0.102 (5)	−0.054 (5)
C3	0.083 (4)	0.085 (4)	0.261 (10)	−0.017 (3)	0.090 (6)	−0.022 (6)
C4	0.052 (3)	0.076 (3)	0.175 (6)	−0.002 (3)	0.045 (4)	0.020 (4)
C5	0.077 (4)	0.095 (5)	0.247 (10)	−0.004 (3)	0.053 (6)	0.030 (6)
C6	0.105 (6)	0.170 (9)	0.208 (10)	−0.025 (6)	0.056 (6)	0.021 (8)
C8	0.094 (4)	0.114 (4)	0.128 (5)	−0.027 (3)	0.054 (4)	−0.001 (4)
C7	0.105 (5)	0.166 (7)	0.129 (6)	−0.022 (5)	0.052 (4)	0.011 (5)
C9	0.067 (3)	0.062 (3)	0.133 (5)	−0.015 (2)	0.048 (3)	0.001 (3)
C10	0.079 (3)	0.066 (3)	0.128 (5)	−0.019 (3)	0.054 (3)	0.003 (3)
C11	0.078 (3)	0.065 (3)	0.143 (4)	−0.006 (3)	0.049 (3)	0.020 (3)
C12	0.077 (3)	0.046 (2)	0.093 (3)	0.000 (2)	0.037 (2)	0.008 (2)
C13	0.087 (3)	0.040 (2)	0.052 (2)	0.004 (2)	0.032 (2)	0.0031 (17)
C14	0.080 (3)	0.051 (2)	0.070 (3)	0.003 (2)	0.035 (2)	−0.0098 (19)
C15	0.076 (3)	0.065 (3)	0.067 (3)	−0.005 (2)	0.026 (2)	−0.006 (2)
C16	0.077 (3)	0.092 (3)	0.064 (3)	0.016 (3)	0.039 (2)	0.015 (3)
C17	0.119 (4)	0.061 (3)	0.068 (3)	0.010 (3)	0.051 (3)	−0.003 (2)
C18	0.098 (3)	0.053 (2)	0.065 (3)	−0.002 (2)	0.038 (2)	−0.001 (2)

Cl1—C16	1.736 (4)	C8—C9	1.451 (7)
O1—C12	1.210 (4)	C8—H8A	0.9300
N1—C12	1.352 (5)	C7—H7A	0.9300
N1—C13	1.411 (5)	C9—C10	1.386 (6)
N1—H1N1	0.98 (5)	C10—C11	1.535 (6)
C1—C10	1.344 (7)	C11—C12	1.518 (6)
C1—C2	1.394 (8)	C11—H11A	0.9700
C1—H1A	0.9300	C11—H11B	0.9700
C2—C3	1.371 (9)	C13—C18	1.368 (5)
C2—H2A	0.9300	C13—C14	1.395 (5)
C3—C4	1.423 (9)	C14—C15	1.371 (5)
C3—H3A	0.9300	C14—H14A	0.9300
C4—C9	1.394 (7)	C15—C16	1.365 (5)
C4—C5	1.420 (10)	C15—H15A	0.9300
C5—C6	1.331 (10)	C16—C17	1.380 (6)
C5—H5A	0.9300	C17—C18	1.365 (6)
C6—C7	1.372 (10)	C17—H17A	0.9300
C6—H6A	0.9300	C18—H18B	0.9300
C8—C7	1.367 (8)
C12—N1—C13	126.7 (3)	C1—C10—C9	118.4 (5)
C12—N1—H1N1	123 (3)	C1—C10—C11	121.6 (6)
C13—N1—H1N1	111 (3)	C9—C10—C11	120.0 (5)
C10—C1—C2	123.6 (6)	C12—C11—C10	114.0 (3)
C10—C1—H1A	118.2	C12—C11—H11A	108.7
C2—C1—H1A	118.2	C10—C11—H11A	108.7
C3—C2—C1	118.6 (7)	C12—C11—H11B	108.7
C3—C2—H2A	120.7	C10—C11—H11B	108.7
C1—C2—H2A	120.7	H11A—C11—H11B	107.6
C2—C3—C4	119.4 (7)	O1—C12—N1	123.1 (4)
C2—C3—H3A	120.3	O1—C12—C11	123.3 (4)
C4—C3—H3A	120.3	N1—C12—C11	113.7 (4)
C9—C4—C5	121.8 (7)	C18—C13—C14	117.8 (4)
C9—C4—C3	119.2 (7)	C18—C13—N1	118.7 (4)
C5—C4—C3	119.0 (7)	C14—C13—N1	123.4 (3)
C6—C5—C4	117.9 (8)	C15—C14—C13	120.7 (4)
C6—C5—H5A	121.0	C15—C14—H14A	119.7
C4—C5—H5A	121.0	C13—C14—H14A	119.7
C5—C6—C7	123.7 (10)	C16—C15—C14	120.1 (4)
C5—C6—H6A	118.2	C16—C15—H15A	119.9
C7—C6—H6A	118.2	C14—C15—H15A	119.9
C7—C8—C9	119.9 (6)	C15—C16—C17	120.0 (4)
C7—C8—H8A	120.0	C15—C16—Cl1	120.0 (4)
C9—C8—H8A	120.0	C17—C16—Cl1	119.9 (4)
C8—C7—C6	120.0 (8)	C18—C17—C16	119.5 (4)
C8—C7—H7A	120.0	C18—C17—H17A	120.2
C6—C7—H7A	120.0	C16—C17—H17A	120.2
C10—C9—C4	120.7 (6)	C17—C18—C13	121.9 (4)
C10—C9—C8	122.6 (5)	C17—C18—H18B	119.1
C4—C9—C8	116.7 (6)	C13—C18—H18B	119.1
C10—C1—C2—C3	−1.4 (8)	C8—C9—C10—C11	0.0 (6)
C1—C2—C3—C4	0.9 (9)	C1—C10—C11—C12	101.4 (5)
C2—C3—C4—C9	0.0 (8)	C9—C10—C11—C12	−79.4 (5)
C2—C3—C4—C5	178.7 (5)	C13—N1—C12—O1	−2.2 (7)
C9—C4—C5—C6	−2.3 (9)	C13—N1—C12—C11	176.7 (4)
C3—C4—C5—C6	179.0 (6)	C10—C11—C12—O1	−10.9 (7)
C4—C5—C6—C7	1.6 (12)	C10—C11—C12—N1	170.2 (4)
C9—C8—C7—C6	−0.6 (8)	C12—N1—C13—C18	149.8 (4)
C5—C6—C7—C8	−0.2 (11)	C12—N1—C13—C14	−31.2 (6)
C5—C4—C9—C10	−179.2 (4)	C18—C13—C14—C15	−1.9 (5)
C3—C4—C9—C10	−0.5 (6)	N1—C13—C14—C15	179.0 (4)
C5—C4—C9—C8	1.6 (6)	C13—C14—C15—C16	0.8 (6)
C3—C4—C9—C8	−179.7 (4)	C14—C15—C16—C17	0.7 (6)
C7—C8—C9—C10	−179.3 (4)	C14—C15—C16—Cl1	−176.3 (3)
C7—C8—C9—C4	−0.2 (7)	C15—C16—C17—C18	−1.0 (6)
C2—C1—C10—C9	0.8 (7)	Cl1—C16—C17—C18	176.0 (3)
C2—C1—C10—C11	−179.9 (4)	C16—C17—C18—C13	−0.2 (6)
C4—C9—C10—C1	0.2 (6)	C14—C13—C18—C17	1.6 (5)
C8—C9—C10—C1	179.3 (4)	N1—C13—C18—C17	−179.3 (3)
C4—C9—C10—C11	−179.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.98 (5)	1.98 (5)	2.942 (4)	166 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.98 (5)	1.98 (5)	2.942 (4)	166 (4)

Symmetry code: (i) .