N-(3,5-Dichloro-phen-yl)-2-(naphthalen-1-yl)acetamide.

In the title compound, C(18)H(13)Cl(2)NO, the naphthalene ring system [maximum deviation = 0.038 (4) Å] and the benzene ring form dihedral angles of 69.5 (2) and 37.2 (2)°, respectively, with the essentially planar acetamide unit [maximum deviation = 0.004 (4) Å]. The naphthalene ring system forms a dihedral angle of 52.36 (18)° with the benzene ring. In the crystal, mol-ecules are linked via inter-molecular N-H⋯O hydrogen bonds, forming chains along [001].

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 related structures, see: Fun et al. (2010 ▶, 2011 ▶); Li & Wu (2010 ▶); Xiao et al. (2010 ▶); Praveen et al. (2011 ▶); Wang et al. (2010 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H13Cl2NO

M = 330.19

Monoclinic,

a = 7.8090 (14) Å

b = 24.811 (4) Å

c = 9.6783 (13) Å

β = 125.05 (1)°

V = 1535.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 296 K

0.38 × 0.29 × 0.06 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.855, T max = 0.974

16035 measured reflections

4453 independent reflections

2621 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.198

S = 1.03

4453 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.33 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/S1600536811041468/lh5351sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041468/lh5351Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041468/lh5351Isup3.cml

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

C18H13Cl2NO	F(000) = 680
Mr = 330.19	Dx = 1.429 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3344 reflections
a = 7.8090 (14) Å	θ = 2.7–29.8°
b = 24.811 (4) Å	µ = 0.42 mm−1
c = 9.6783 (13) Å	T = 296 K
β = 125.05 (1)°	Plate, colourless
V = 1535.1 (4) Å3	0.38 × 0.29 × 0.06 mm
Z = 4

Bruker SMART APEXII DUO CCD area-detector diffractometer	4453 independent reflections
Radiation source: fine-focus sealed tube	2621 reflections with I > 2σ(I)
graphite	Rint = 0.051
φ and ω scans	θmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→8
Tmin = 0.855, Tmax = 0.974	k = −33→34
16035 measured reflections	l = −13→13

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0681P)2 + 1.5936P] where P = (Fo2 + 2Fc2)/3
4453 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.33 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
Cl1	0.6802 (2)	0.95869 (4)	0.44624 (14)	0.0775 (4)
Cl2	0.27251 (17)	0.91840 (5)	−0.21419 (12)	0.0771 (3)
O1	0.8282 (4)	0.75802 (9)	0.4568 (3)	0.0637 (7)
N1	0.8058 (4)	0.78590 (10)	0.2249 (3)	0.0414 (6)
C1	0.7351 (5)	0.86778 (12)	0.3249 (4)	0.0420 (6)
H1A	0.8298	0.8575	0.4369	0.050*
C2	0.6296 (5)	0.91611 (12)	0.2847 (4)	0.0485 (7)
C3	0.4862 (5)	0.93244 (13)	0.1200 (4)	0.0511 (8)
H3A	0.4155	0.9651	0.0954	0.061*
C4	0.4521 (5)	0.89863 (13)	−0.0058 (4)	0.0488 (7)
C5	0.5533 (5)	0.85030 (12)	0.0274 (4)	0.0440 (7)
H5A	0.5265	0.8282	−0.0606	0.053*
C6	0.6960 (4)	0.83471 (11)	0.1934 (3)	0.0377 (6)
C7	0.8686 (5)	0.75141 (12)	0.3535 (4)	0.0438 (7)
C8	0.9966 (6)	0.70397 (14)	0.3588 (5)	0.0580 (9)
H8A	0.9423	0.6935	0.2440	0.070*
H8B	1.1401	0.7156	0.4125	0.070*
C9	0.9946 (5)	0.65549 (13)	0.4519 (4)	0.0484 (7)
C10	0.8751 (6)	0.61214 (15)	0.3661 (6)	0.0665 (10)
H10A	0.7960	0.6125	0.2488	0.080*
C11	0.8659 (7)	0.56650 (17)	0.4478 (7)	0.0776 (13)
H11A	0.7824	0.5373	0.3852	0.093*
C12	0.9787 (8)	0.56556 (16)	0.6169 (8)	0.0826 (14)
H12A	0.9710	0.5356	0.6707	0.099*
C13	1.1104 (5)	0.60953 (14)	0.7160 (5)	0.0558 (9)
C14	1.2266 (8)	0.6089 (2)	0.8930 (7)	0.0880 (15)
H14A	1.2177	0.5794	0.9480	0.106*
C15	1.3489 (8)	0.6501 (3)	0.9818 (7)	0.0930 (16)
H15A	1.4222	0.6496	1.0987	0.112*
C16	1.3700 (6)	0.6941 (2)	0.9035 (6)	0.0808 (13)
H16A	1.4621	0.7217	0.9691	0.097*
C17	1.2573 (5)	0.69744 (16)	0.7315 (5)	0.0622 (9)
H17A	1.2705	0.7274	0.6807	0.075*
C18	1.1179 (5)	0.65423 (13)	0.6294 (4)	0.0464 (7)
H1N1	0.822 (5)	0.7771 (14)	0.154 (5)	0.055 (10)*

	U11	U22	U33	U12	U13	U23
Cl1	0.1246 (9)	0.0497 (5)	0.0709 (6)	0.0016 (5)	0.0636 (7)	−0.0107 (4)
Cl2	0.0783 (6)	0.0938 (8)	0.0501 (5)	0.0249 (5)	0.0315 (5)	0.0248 (5)
O1	0.1054 (19)	0.0600 (15)	0.0634 (15)	0.0303 (13)	0.0705 (15)	0.0228 (12)
N1	0.0576 (15)	0.0437 (14)	0.0380 (13)	0.0069 (11)	0.0363 (12)	0.0059 (10)
C1	0.0505 (16)	0.0400 (16)	0.0393 (14)	−0.0035 (12)	0.0280 (13)	0.0014 (12)
C2	0.0622 (19)	0.0408 (17)	0.0527 (18)	−0.0036 (14)	0.0388 (16)	−0.0025 (14)
C3	0.0610 (19)	0.0444 (18)	0.058 (2)	0.0096 (14)	0.0401 (17)	0.0085 (14)
C4	0.0522 (17)	0.0537 (19)	0.0464 (17)	0.0050 (14)	0.0318 (15)	0.0125 (14)
C5	0.0535 (17)	0.0475 (18)	0.0398 (15)	−0.0035 (13)	0.0319 (14)	0.0020 (12)
C6	0.0445 (15)	0.0372 (15)	0.0384 (14)	−0.0011 (11)	0.0279 (13)	0.0029 (11)
C7	0.0585 (17)	0.0451 (16)	0.0429 (15)	0.0079 (13)	0.0380 (15)	0.0071 (12)
C8	0.082 (2)	0.058 (2)	0.061 (2)	0.0252 (17)	0.057 (2)	0.0190 (16)
C9	0.0566 (18)	0.0458 (18)	0.0555 (19)	0.0134 (14)	0.0395 (16)	0.0054 (14)
C10	0.063 (2)	0.057 (2)	0.081 (3)	0.0047 (17)	0.042 (2)	−0.017 (2)
C11	0.083 (3)	0.050 (2)	0.119 (4)	−0.0045 (19)	0.069 (3)	−0.018 (2)
C12	0.106 (3)	0.047 (2)	0.141 (5)	0.020 (2)	0.098 (4)	0.020 (3)
C13	0.0616 (19)	0.054 (2)	0.069 (2)	0.0263 (16)	0.0474 (18)	0.0243 (17)
C14	0.101 (4)	0.105 (4)	0.084 (3)	0.050 (3)	0.068 (3)	0.045 (3)
C15	0.072 (3)	0.134 (5)	0.066 (3)	0.033 (3)	0.035 (2)	0.022 (3)
C16	0.047 (2)	0.114 (4)	0.064 (3)	−0.002 (2)	0.0219 (19)	−0.014 (3)
C17	0.0520 (19)	0.073 (2)	0.067 (2)	0.0016 (17)	0.0376 (18)	−0.0055 (19)
C18	0.0479 (16)	0.0506 (18)	0.0517 (17)	0.0164 (13)	0.0350 (15)	0.0117 (14)

Cl1—C2	1.734 (3)	C9—C10	1.352 (5)
Cl2—C4	1.740 (3)	C9—C18	1.407 (4)
O1—C7	1.220 (3)	C10—C11	1.406 (6)
N1—C7	1.349 (4)	C10—H10A	0.9300
N1—C6	1.412 (4)	C11—C12	1.341 (7)
N1—H1N1	0.80 (4)	C11—H11A	0.9300
C1—C2	1.378 (4)	C12—C13	1.426 (6)
C1—C6	1.393 (4)	C12—H12A	0.9300
C1—H1A	0.9300	C13—C14	1.405 (6)
C2—C3	1.381 (5)	C13—C18	1.411 (4)
C3—C4	1.373 (5)	C14—C15	1.325 (7)
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.369 (4)	C15—C16	1.392 (7)
C5—C6	1.385 (4)	C15—H15A	0.9300
C5—H5A	0.9300	C16—C17	1.367 (6)
C7—C8	1.526 (4)	C16—H16A	0.9300
C8—C9	1.509 (5)	C17—C18	1.441 (5)
C8—H8A	0.9700	C17—H17A	0.9300
C8—H8B	0.9700
C7—N1—C6	126.6 (2)	C10—C9—C18	118.6 (3)
C7—N1—H1N1	118 (3)	C10—C9—C8	120.5 (3)
C6—N1—H1N1	115 (3)	C18—C9—C8	120.8 (3)
C2—C1—C6	118.2 (3)	C9—C10—C11	122.4 (4)
C2—C1—H1A	120.9	C9—C10—H10A	118.8
C6—C1—H1A	120.9	C11—C10—H10A	118.8
C1—C2—C3	122.6 (3)	C12—C11—C10	119.4 (4)
C1—C2—Cl1	119.1 (2)	C12—C11—H11A	120.3
C3—C2—Cl1	118.4 (2)	C10—C11—H11A	120.3
C4—C3—C2	117.4 (3)	C11—C12—C13	121.4 (4)
C4—C3—H3A	121.3	C11—C12—H12A	119.3
C2—C3—H3A	121.3	C13—C12—H12A	119.3
C5—C4—C3	122.4 (3)	C14—C13—C18	121.0 (4)
C5—C4—Cl2	119.4 (3)	C14—C13—C12	121.5 (4)
C3—C4—Cl2	118.2 (3)	C18—C13—C12	117.5 (4)
C4—C5—C6	119.2 (3)	C15—C14—C13	120.2 (5)
C4—C5—H5A	120.4	C15—C14—H14A	119.9
C6—C5—H5A	120.4	C13—C14—H14A	119.9
C5—C6—C1	120.3 (3)	C14—C15—C16	121.3 (5)
C5—C6—N1	118.3 (3)	C14—C15—H15A	119.4
C1—C6—N1	121.4 (3)	C16—C15—H15A	119.4
O1—C7—N1	122.9 (3)	C17—C16—C15	121.0 (5)
O1—C7—C8	123.3 (3)	C17—C16—H16A	119.5
N1—C7—C8	113.8 (2)	C15—C16—H16A	119.5
C9—C8—C7	113.8 (3)	C16—C17—C18	119.7 (4)
C9—C8—H8A	108.8	C16—C17—H17A	120.2
C7—C8—H8A	108.8	C18—C17—H17A	120.2
C9—C8—H8B	108.8	C9—C18—C13	120.6 (3)
C7—C8—H8B	108.8	C9—C18—C17	122.6 (3)
H8A—C8—H8B	107.7	C13—C18—C17	116.8 (3)
C6—C1—C2—C3	0.7 (5)	C8—C9—C10—C11	−178.9 (3)
C6—C1—C2—Cl1	−178.5 (2)	C9—C10—C11—C12	0.2 (6)
C1—C2—C3—C4	−0.6 (5)	C10—C11—C12—C13	−0.9 (6)
Cl1—C2—C3—C4	178.6 (2)	C11—C12—C13—C14	179.2 (4)
C2—C3—C4—C5	0.4 (5)	C11—C12—C13—C18	−0.1 (5)
C2—C3—C4—Cl2	−179.9 (2)	C18—C13—C14—C15	−1.3 (6)
C3—C4—C5—C6	−0.2 (5)	C12—C13—C14—C15	179.4 (4)
Cl2—C4—C5—C6	−180.0 (2)	C13—C14—C15—C16	−1.7 (7)
C4—C5—C6—C1	0.3 (4)	C14—C15—C16—C17	3.1 (7)
C4—C5—C6—N1	−177.1 (3)	C15—C16—C17—C18	−1.4 (6)
C2—C1—C6—C5	−0.5 (4)	C10—C9—C18—C13	−2.6 (4)
C2—C1—C6—N1	176.8 (3)	C8—C9—C18—C13	177.9 (3)
C7—N1—C6—C5	−146.4 (3)	C10—C9—C18—C17	177.1 (3)
C7—N1—C6—C1	36.2 (4)	C8—C9—C18—C17	−2.4 (4)
C6—N1—C7—O1	3.1 (5)	C14—C13—C18—C9	−177.4 (3)
C6—N1—C7—C8	−176.2 (3)	C12—C13—C18—C9	1.9 (4)
O1—C7—C8—C9	23.7 (5)	C14—C13—C18—C17	2.9 (5)
N1—C7—C8—C9	−157.1 (3)	C12—C13—C18—C17	−177.9 (3)
C7—C8—C9—C10	103.2 (4)	C16—C17—C18—C9	178.8 (3)
C7—C8—C9—C18	−77.3 (4)	C16—C17—C18—C13	−1.5 (5)
C18—C9—C10—C11	1.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.80 (4)	2.12 (4)	2.911 (4)	170 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.80 (4)	2.12 (4)	2.911 (4)	170 (4)

Symmetry code: (i) .