N-(2,6-Dichloro-phen-yl)-2-(naphthalen-1-yl)acetamide.

In the title compound, C(18)H(13)Cl(2)NO, the naphthalene ring system and the benzene ring form dihedral angles of 74.73 (13) and 62.53 (16)°, respectively, with the acetamide grouping [maximum deviation = 0.005 (3) Å]. The naphthalene ring system forms a dihedral angle of 75.14 (13)° with the benzene ring. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming C(4) chains propagating in [010]. The O atom also accepts two C-H⋯O inter-actions.

Related literature

For related structures, see: Fun et al. (2010 ▶, 2011a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H13Cl2NO

M = 330.19

Monoclinic,

a = 13.1918 (13) Å

b = 4.7199 (5) Å

c = 24.878 (2) Å

β = 103.127 (3)°

V = 1508.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 100 K

0.38 × 0.13 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.853, T max = 0.968

13545 measured reflections

4397 independent reflections

3245 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.168

S = 1.08

4397 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.56 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/S1600536812014869/hb6731sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014869/hb6731Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812014869/hb6731Isup3.cml

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

C18H13Cl2NO	F(000) = 680
Mr = 330.19	Dx = 1.454 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3979 reflections
a = 13.1918 (13) Å	θ = 3.2–30.0°
b = 4.7199 (5) Å	µ = 0.43 mm−1
c = 24.878 (2) Å	T = 100 K
β = 103.127 (3)°	Needle, colourless
V = 1508.5 (3) Å3	0.38 × 0.13 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4397 independent reflections
Radiation source: fine-focus sealed tube	3245 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 30.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
Tmin = 0.853, Tmax = 0.968	k = −6→6
13545 measured reflections	l = −35→35

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0606P)2 + 3.359P] where P = (Fo2 + 2Fc2)/3
4397 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.46301 (6)	0.58083 (17)	1.15354 (3)	0.02081 (18)
Cl2	0.13465 (6)	−0.0073 (2)	1.03531 (3)	0.0258 (2)
O1	0.36215 (16)	−0.0699 (5)	1.02088 (9)	0.0167 (4)
N1	0.32626 (19)	0.3664 (5)	1.04970 (10)	0.0128 (5)
C1	0.3584 (2)	0.3527 (7)	1.15041 (12)	0.0160 (6)
C2	0.3352 (2)	0.2594 (8)	1.19925 (13)	0.0221 (7)
H2A	0.3758	0.3204	1.2339	0.026*
C3	0.2519 (3)	0.0759 (8)	1.19680 (14)	0.0247 (7)
H3A	0.2357	0.0096	1.2299	0.030*
C4	0.1922 (3)	−0.0109 (7)	1.14604 (14)	0.0234 (7)
H4A	0.1355	−0.1375	1.1444	0.028*
C5	0.2158 (2)	0.0887 (7)	1.09772 (13)	0.0186 (6)
C6	0.3005 (2)	0.2685 (6)	1.09881 (11)	0.0136 (5)
C7	0.3562 (2)	0.1873 (6)	1.01372 (11)	0.0123 (5)
C8	0.3845 (2)	0.3240 (6)	0.96339 (11)	0.0125 (5)
H8A	0.3733	0.5311	0.9645	0.015*
H8B	0.4592	0.2910	0.9649	0.015*
C9	0.3199 (2)	0.2055 (6)	0.90964 (11)	0.0128 (5)
C10	0.3612 (2)	0.0027 (7)	0.88140 (12)	0.0156 (6)
H10A	0.4293	−0.0667	0.8965	0.019*
C11	0.3044 (2)	−0.1058 (7)	0.83020 (12)	0.0183 (6)
H11A	0.3343	−0.2474	0.8114	0.022*
C12	0.2067 (2)	−0.0057 (7)	0.80799 (12)	0.0177 (6)
H12A	0.1691	−0.0769	0.7735	0.021*
C13	0.1607 (2)	0.2029 (6)	0.83576 (12)	0.0151 (6)
C14	0.0590 (2)	0.3104 (7)	0.81287 (12)	0.0189 (6)
H14A	0.0213	0.2416	0.7782	0.023*
C15	0.0150 (2)	0.5103 (8)	0.83999 (13)	0.0213 (6)
H15A	−0.0527	0.5800	0.8240	0.026*
C16	0.0700 (2)	0.6148 (7)	0.89197 (13)	0.0199 (6)
H16A	0.0387	0.7521	0.9110	0.024*
C17	0.1686 (2)	0.5172 (7)	0.91479 (12)	0.0171 (6)
H17A	0.2052	0.5902	0.9494	0.021*
C18	0.2165 (2)	0.3100 (6)	0.88767 (12)	0.0140 (5)
H1N1	0.332 (3)	0.543 (8)	1.0462 (14)	0.014 (9)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0224 (3)	0.0174 (4)	0.0219 (4)	−0.0038 (3)	0.0033 (3)	−0.0046 (3)
Cl2	0.0198 (3)	0.0294 (5)	0.0285 (4)	−0.0066 (3)	0.0058 (3)	−0.0084 (3)
O1	0.0234 (10)	0.0077 (10)	0.0203 (10)	0.0022 (8)	0.0077 (8)	−0.0007 (8)
N1	0.0208 (11)	0.0034 (12)	0.0152 (11)	0.0017 (9)	0.0057 (9)	0.0020 (9)
C1	0.0189 (13)	0.0116 (14)	0.0176 (13)	0.0024 (11)	0.0045 (10)	0.0000 (11)
C2	0.0277 (15)	0.0230 (18)	0.0161 (14)	0.0069 (14)	0.0062 (11)	0.0013 (13)
C3	0.0322 (16)	0.0236 (18)	0.0224 (15)	0.0066 (15)	0.0148 (13)	0.0064 (14)
C4	0.0271 (15)	0.0159 (16)	0.0317 (17)	0.0004 (13)	0.0163 (13)	0.0055 (14)
C5	0.0205 (13)	0.0154 (15)	0.0211 (14)	0.0029 (12)	0.0070 (11)	−0.0011 (12)
C6	0.0196 (13)	0.0059 (13)	0.0170 (13)	0.0030 (11)	0.0077 (10)	0.0021 (10)
C7	0.0132 (11)	0.0091 (13)	0.0142 (12)	0.0003 (10)	0.0021 (9)	−0.0017 (11)
C8	0.0161 (12)	0.0068 (12)	0.0148 (12)	−0.0002 (10)	0.0041 (10)	−0.0002 (10)
C9	0.0161 (12)	0.0091 (13)	0.0139 (12)	−0.0023 (11)	0.0051 (10)	0.0015 (11)
C10	0.0182 (12)	0.0120 (14)	0.0172 (13)	−0.0008 (12)	0.0052 (10)	0.0002 (11)
C11	0.0257 (14)	0.0131 (15)	0.0174 (13)	0.0008 (12)	0.0075 (11)	−0.0030 (12)
C12	0.0238 (14)	0.0140 (14)	0.0146 (13)	−0.0025 (12)	0.0032 (10)	−0.0021 (12)
C13	0.0192 (13)	0.0108 (14)	0.0154 (13)	−0.0045 (11)	0.0042 (10)	0.0009 (11)
C14	0.0200 (13)	0.0174 (16)	0.0175 (14)	−0.0017 (12)	0.0004 (11)	0.0010 (12)
C15	0.0151 (12)	0.0230 (17)	0.0248 (15)	0.0009 (12)	0.0029 (11)	0.0031 (13)
C16	0.0220 (14)	0.0157 (16)	0.0231 (15)	0.0017 (12)	0.0075 (11)	−0.0010 (12)
C17	0.0208 (13)	0.0136 (14)	0.0175 (13)	0.0006 (12)	0.0054 (10)	−0.0002 (12)
C18	0.0164 (12)	0.0098 (13)	0.0164 (13)	−0.0009 (11)	0.0053 (10)	0.0006 (11)

Cl1—C1	1.738 (3)	C9—C10	1.371 (4)
Cl2—C5	1.734 (3)	C9—C18	1.436 (4)
O1—C7	1.227 (4)	C10—C11	1.418 (4)
N1—C7	1.354 (4)	C10—H10A	0.9500
N1—C6	1.418 (4)	C11—C12	1.367 (4)
N1—H1N1	0.85 (4)	C11—H11A	0.9500
C1—C2	1.390 (4)	C12—C13	1.416 (4)
C1—C6	1.394 (4)	C12—H12A	0.9500
C2—C3	1.390 (5)	C13—C18	1.426 (4)
C2—H2A	0.9500	C13—C14	1.426 (4)
C3—C4	1.390 (5)	C14—C15	1.364 (5)
C3—H3A	0.9500	C14—H14A	0.9500
C4—C5	1.390 (4)	C15—C16	1.420 (4)
C4—H4A	0.9500	C15—H15A	0.9500
C5—C6	1.398 (4)	C16—C17	1.375 (4)
C7—C8	1.528 (4)	C16—H16A	0.9500
C8—C9	1.520 (4)	C17—C18	1.416 (4)
C8—H8A	0.9900	C17—H17A	0.9500
C8—H8B	0.9900
C7—N1—C6	122.0 (3)	C10—C9—C18	119.9 (3)
C7—N1—H1N1	120 (2)	C10—C9—C8	119.9 (3)
C6—N1—H1N1	117 (2)	C18—C9—C8	120.2 (2)
C2—C1—C6	122.1 (3)	C9—C10—C11	121.5 (3)
C2—C1—Cl1	119.1 (2)	C9—C10—H10A	119.3
C6—C1—Cl1	118.8 (2)	C11—C10—H10A	119.3
C3—C2—C1	119.2 (3)	C12—C11—C10	119.7 (3)
C3—C2—H2A	120.4	C12—C11—H11A	120.2
C1—C2—H2A	120.4	C10—C11—H11A	120.2
C4—C3—C2	120.2 (3)	C11—C12—C13	120.8 (3)
C4—C3—H3A	119.9	C11—C12—H12A	119.6
C2—C3—H3A	119.9	C13—C12—H12A	119.6
C3—C4—C5	119.6 (3)	C12—C13—C18	119.9 (3)
C3—C4—H4A	120.2	C12—C13—C14	121.4 (3)
C5—C4—H4A	120.2	C18—C13—C14	118.7 (3)
C4—C5—C6	121.6 (3)	C15—C14—C13	121.1 (3)
C4—C5—Cl2	118.1 (3)	C15—C14—H14A	119.5
C6—C5—Cl2	120.3 (2)	C13—C14—H14A	119.5
C1—C6—C5	117.3 (3)	C14—C15—C16	120.3 (3)
C1—C6—N1	120.8 (3)	C14—C15—H15A	119.9
C5—C6—N1	121.9 (3)	C16—C15—H15A	119.9
O1—C7—N1	122.7 (3)	C17—C16—C15	120.0 (3)
O1—C7—C8	121.2 (3)	C17—C16—H16A	120.0
N1—C7—C8	116.1 (3)	C15—C16—H16A	120.0
C9—C8—C7	111.9 (2)	C16—C17—C18	121.1 (3)
C9—C8—H8A	109.2	C16—C17—H17A	119.4
C7—C8—H8A	109.2	C18—C17—H17A	119.4
C9—C8—H8B	109.2	C17—C18—C13	118.8 (3)
C7—C8—H8B	109.2	C17—C18—C9	122.9 (3)
H8A—C8—H8B	107.9	C13—C18—C9	118.2 (3)
C6—C1—C2—C3	0.1 (5)	C18—C9—C10—C11	0.7 (4)
Cl1—C1—C2—C3	−179.7 (3)	C8—C9—C10—C11	−177.9 (3)
C1—C2—C3—C4	−0.5 (5)	C9—C10—C11—C12	0.5 (5)
C2—C3—C4—C5	−0.5 (5)	C10—C11—C12—C13	−0.8 (5)
C3—C4—C5—C6	1.9 (5)	C11—C12—C13—C18	−0.2 (5)
C3—C4—C5—Cl2	−176.1 (3)	C11—C12—C13—C14	179.6 (3)
C2—C1—C6—C5	1.2 (4)	C12—C13—C14—C15	179.7 (3)
Cl1—C1—C6—C5	−178.9 (2)	C18—C13—C14—C15	−0.5 (5)
C2—C1—C6—N1	−179.8 (3)	C13—C14—C15—C16	−0.2 (5)
Cl1—C1—C6—N1	0.1 (4)	C14—C15—C16—C17	0.9 (5)
C4—C5—C6—C1	−2.3 (4)	C15—C16—C17—C18	−0.8 (5)
Cl2—C5—C6—C1	175.8 (2)	C16—C17—C18—C13	0.1 (5)
C4—C5—C6—N1	178.7 (3)	C16—C17—C18—C9	179.0 (3)
Cl2—C5—C6—N1	−3.2 (4)	C12—C13—C18—C17	−179.6 (3)
C7—N1—C6—C1	117.3 (3)	C14—C13—C18—C17	0.5 (4)
C7—N1—C6—C5	−63.7 (4)	C12—C13—C18—C9	1.4 (4)
C6—N1—C7—O1	0.6 (4)	C14—C13—C18—C9	−178.4 (3)
C6—N1—C7—C8	−178.3 (2)	C10—C9—C18—C17	179.4 (3)
O1—C7—C8—C9	57.7 (3)	C8—C9—C18—C17	−2.0 (4)
N1—C7—C8—C9	−123.3 (3)	C10—C9—C18—C13	−1.7 (4)
C7—C8—C9—C10	−99.9 (3)	C8—C9—C18—C13	176.9 (3)
C7—C8—C9—C18	81.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.84 (4)	2.00 (4)	2.823 (3)	165 (3)
C8—H8A···O1i	0.99	2.37	3.242 (4)	146
C8—H8B···O1ii	0.99	2.53	3.488 (4)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.84 (4)	2.00 (4)	2.823 (3)	165 (3)
C8—H8A⋯O1i	0.99	2.37	3.242 (4)	146
C8—H8B⋯O1ii	0.99	2.53	3.488 (4)	163

Symmetry codes: (i) ; (ii) .