N-(4-Chloro­phen­yl)-2-(naphthalen-1-yl)acetamide

Fun, H.-K.; Quah, C.K.; Nayak, P.S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812031613

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2463

https://doi.org/10.1107/S1600536812031613

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N-(4-Chlorophenyl)-2-(naphthalen-1-yl)acetamide

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Prakash S. Nayak,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 8 July 2012; accepted 11 July 2012; online 18 July 2012)

In the title compound, C₁₈H₁₄ClNO, 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, molecules 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_r = 295.75
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.060
wR(F²) = 0.208
S = 1.01
2611 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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) x, y+1, z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812031613/hb6893sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031613/hb6893Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812031613/hb6893Isup3.cml

checkCIF report

Comment top

In continuation of our work on synthesis of amides (Fun et al., 2010, 2011a,b, 2012), we report herein the crystal structure of the title compound.

The molecular structure is shown in Fig. 1. Bond lengths are comparable to related structures (Fun et al., 2010, 2011a,b, 2012). The naphthalene ring system (C1–C10, maximum deviation of 0.014 (9) Å at atom C5) forms a dihedral angle of 74.8 (2)° with the benzene ring (C13–C18).

In the crystal structure, Fig. 2, molecules are linked via N1—H1N1···O1 hydrogen bonds (Table 1) into one-dimensional chains along [010].

Related literature top

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

Experimental top

1-Naphthalene acetic acid (0.186 g, 1 mmol), 4-chloroaniline (0.127 g, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) were dissolved in dichloromethane (20 ml). The mixture was stirred in presence of triethylamine at 273 K for about 3 h. The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring, which was extracted thrice with dichloromethane. Organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound. Colourless blocks were grown from acetone and toluene (1:1) mixture by the slow evaporation method (m.p. 449–451 K).

Structure description top

In continuation of our work on synthesis of amides (Fun et al., 2010, 2011a,b, 2012), we report herein the crystal structure of the title compound.

In the crystal structure, Fig. 2, molecules are linked via N1—H1N1···O1 hydrogen bonds (Table 1) into one-dimensional chains along [010].

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

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

N-(4-Chlorophenyl)-2-(naphthalen-1-yl)acetamide top

Crystal data top

C₁₈H₁₄ClNO	F(000) = 616
M_r = 295.75	D_x = 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 × 0.14 × 0.09 mm
Z = 4

Data collection top

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

Refinement top

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(F_o²) + (0.0913P)² + 0.5172P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
2611 reflections	Δρ_max = 0.32 e Å⁻³
195 parameters	Δρ_min = −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)

Crystal data top

C₁₈H₁₄ClNO	V = 1494.6 (7) Å³
M_r = 295.75	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.163 (6) Å	µ = 0.25 mm⁻¹
b = 5.0458 (11) Å	T = 296 K
c = 17.252 (4) Å	0.35 × 0.14 × 0.09 mm
β = 116.365 (5)°

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	2611 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1185 reflections with I > 2σ(I)
T_min = 0.916, T_max = 0.978	R_int = 0.050
9206 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.208	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.32 e Å⁻³
2611 reflections	Δρ_min = −0.18 e Å⁻³
195 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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄ClNO
M_r	295.75
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	19.163 (6), 5.0458 (11), 17.252 (4)
β (°)	116.365 (5)
V (Å³)	1494.6 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.35 × 0.14 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.916, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	9206, 2611, 1185
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.208, 1.01
No. of reflections	2611
No. of parameters	195
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.18

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). BN also thanks UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP-DRS-Phase 1 programme.

References

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