N-(3-Chloro-4-fluoro-phen-yl)-2-(naphthalen-1-yl)acetamide.

In the title compound, C(18)H(13)ClFNO, the dihedral angle between the mean planes of the chloro- and fluoro-substituted benzene ring and the naphthalene ring system is 60.5 (8)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming a zigzag chain along [101].

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: Davis & Healy (2010 ▶); Li et al. (2010 ▶); Li & Wu (2010 ▶); Wang et al. (2010 ▶); Xiao et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H13ClFNO

M = 313.74

Monoclinic,

a = 8.096 (6) Å

b = 23.323 (6) Å

c = 8.404 (3) Å

β = 110.83 (5)°

V = 1483.4 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 173 K

0.30 × 0.18 × 0.10 mm

Data collection

Oxford Diffraction Oxford Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.924, T max = 0.974

13979 measured reflections

3679 independent reflections

2947 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.119

S = 1.04

3679 reflections

202 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024597/is2737sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024597/is2737Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024597/is2737Isup3.cml

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

C18H13ClFNO	F(000) = 648
Mr = 313.74	Dx = 1.405 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4655 reflections
a = 8.096 (6) Å	θ = 3.1–32.5°
b = 23.323 (6) Å	µ = 0.27 mm−1
c = 8.404 (3) Å	T = 173 K
β = 110.83 (5)°	Block, colorless
V = 1483.4 (13) Å3	0.30 × 0.18 × 0.10 mm
Z = 4

Oxford Diffraction Oxford Xcalibur Eos Gemini diffractometer	3679 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2947 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 16.1500 pixels mm-1	θmax = 28.3°, θmin = 3.1°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −31→31
Tmin = 0.924, Tmax = 0.974	l = −10→11
13979 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0495P)2 + 0.4725P] where P = (Fo2 + 2Fc2)/3
3679 reflections	(Δ/σ)max = 0.001
202 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.31 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 > σ(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	0.38936 (7)	0.11723 (2)	1.00561 (6)	0.06507 (18)
F1	0.17103 (16)	0.03432 (5)	0.75440 (15)	0.0629 (3)
O1	0.21705 (14)	0.22471 (5)	0.22432 (14)	0.0486 (3)
N1	0.43807 (16)	0.20845 (6)	0.47811 (16)	0.0379 (3)
H1N	0.538 (2)	0.2204 (7)	0.544 (2)	0.046*
C1	0.4025 (2)	0.16306 (7)	0.71760 (19)	0.0380 (3)
H1B	0.4762	0.1917	0.7880	0.046*
C2	0.3379 (2)	0.11924 (7)	0.7882 (2)	0.0414 (4)
C3	0.2317 (2)	0.07766 (7)	0.6847 (2)	0.0428 (4)
C4	0.1869 (2)	0.07943 (7)	0.5115 (2)	0.0426 (4)
H4A	0.1126	0.0507	0.4417	0.051*
C5	0.2506 (2)	0.12309 (6)	0.43962 (19)	0.0385 (3)
H5A	0.2205	0.1247	0.3197	0.046*
C6	0.35908 (18)	0.16496 (6)	0.54278 (18)	0.0346 (3)
C7	0.36895 (18)	0.23348 (6)	0.32430 (18)	0.0347 (3)
C8	0.4966 (2)	0.27172 (7)	0.2798 (2)	0.0407 (3)
H8A	0.5850	0.2870	0.3858	0.049*
H8B	0.5604	0.2488	0.2209	0.049*
C9	0.40433 (19)	0.32093 (6)	0.16728 (19)	0.0373 (3)
C10	0.3683 (2)	0.31871 (8)	−0.0039 (2)	0.0460 (4)
H10A	0.4071	0.2866	−0.0507	0.055*
C11	0.2745 (2)	0.36315 (9)	−0.1131 (2)	0.0555 (5)
H11A	0.2509	0.3606	−0.2320	0.067*
C12	0.2185 (2)	0.40899 (8)	−0.0499 (2)	0.0545 (5)
H12A	0.1538	0.4383	−0.1248	0.065*
C13	0.2547 (2)	0.41419 (7)	0.1263 (2)	0.0449 (4)
C14	0.2016 (3)	0.46210 (8)	0.1974 (3)	0.0609 (5)
H14A	0.1363	0.4918	0.1247	0.073*
C15	0.2418 (3)	0.46677 (9)	0.3675 (3)	0.0695 (6)
H15A	0.2056	0.4997	0.4130	0.083*
C16	0.3361 (3)	0.42340 (9)	0.4765 (3)	0.0633 (5)
H16A	0.3648	0.4274	0.5958	0.076*
C17	0.3873 (2)	0.37576 (7)	0.4146 (2)	0.0482 (4)
H17A	0.4493	0.3463	0.4906	0.058*
C18	0.34938 (19)	0.36936 (7)	0.2373 (2)	0.0384 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.0760 (4)	0.0795 (4)	0.0392 (2)	−0.0043 (3)	0.0199 (2)	0.0062 (2)
F1	0.0707 (7)	0.0521 (6)	0.0693 (7)	−0.0078 (5)	0.0291 (6)	0.0142 (5)
O1	0.0360 (6)	0.0473 (6)	0.0456 (6)	−0.0067 (5)	−0.0064 (5)	0.0111 (5)
N1	0.0282 (6)	0.0420 (7)	0.0344 (6)	−0.0039 (5)	−0.0002 (5)	0.0035 (5)
C1	0.0342 (7)	0.0390 (8)	0.0366 (7)	0.0023 (6)	0.0072 (6)	−0.0021 (6)
C2	0.0395 (8)	0.0478 (9)	0.0359 (7)	0.0078 (7)	0.0120 (6)	0.0047 (6)
C3	0.0392 (8)	0.0380 (8)	0.0522 (9)	0.0042 (6)	0.0175 (7)	0.0077 (7)
C4	0.0385 (8)	0.0351 (7)	0.0492 (9)	−0.0008 (6)	0.0096 (7)	−0.0033 (6)
C5	0.0363 (8)	0.0395 (8)	0.0353 (7)	0.0004 (6)	0.0072 (6)	−0.0018 (6)
C6	0.0273 (6)	0.0363 (7)	0.0358 (7)	0.0044 (5)	0.0060 (6)	0.0029 (6)
C7	0.0307 (7)	0.0316 (7)	0.0352 (7)	0.0031 (5)	0.0037 (6)	0.0001 (5)
C8	0.0315 (7)	0.0425 (8)	0.0433 (8)	0.0013 (6)	0.0073 (6)	0.0056 (6)
C9	0.0296 (7)	0.0401 (8)	0.0374 (7)	−0.0049 (6)	0.0058 (6)	0.0060 (6)
C10	0.0420 (9)	0.0526 (10)	0.0402 (8)	−0.0100 (7)	0.0107 (7)	−0.0010 (7)
C11	0.0505 (10)	0.0740 (13)	0.0348 (8)	−0.0145 (9)	0.0064 (7)	0.0117 (8)
C12	0.0429 (9)	0.0570 (11)	0.0527 (10)	−0.0052 (8)	0.0037 (8)	0.0241 (8)
C13	0.0333 (8)	0.0420 (8)	0.0544 (9)	−0.0035 (6)	0.0094 (7)	0.0135 (7)
C14	0.0519 (11)	0.0419 (9)	0.0868 (15)	0.0050 (8)	0.0222 (10)	0.0154 (9)
C15	0.0762 (14)	0.0506 (11)	0.0893 (16)	0.0019 (10)	0.0386 (13)	−0.0080 (11)
C16	0.0754 (14)	0.0589 (12)	0.0604 (12)	−0.0043 (10)	0.0302 (11)	−0.0072 (9)
C17	0.0509 (10)	0.0481 (9)	0.0428 (9)	−0.0026 (7)	0.0133 (8)	0.0034 (7)
C18	0.0309 (7)	0.0390 (8)	0.0414 (8)	−0.0050 (6)	0.0081 (6)	0.0063 (6)

Cl1—C2	1.7242 (17)	C9—C10	1.363 (2)
F1—C3	1.3454 (19)	C9—C18	1.416 (2)
O1—C7	1.235 (2)	C10—C11	1.414 (3)
N1—C7	1.3457 (19)	C10—H10A	0.9500
N1—C6	1.407 (2)	C11—C12	1.343 (3)
N1—H1N	0.849 (14)	C11—H11A	0.9500
C1—C2	1.375 (2)	C12—C13	1.409 (3)
C1—C6	1.385 (2)	C12—H12A	0.9500
C1—H1B	0.9500	C13—C14	1.405 (3)
C2—C3	1.380 (2)	C13—C18	1.429 (2)
C3—C4	1.370 (2)	C14—C15	1.353 (3)
C4—C5	1.375 (2)	C14—H14A	0.9500
C4—H4A	0.9500	C15—C16	1.396 (3)
C5—C6	1.391 (2)	C15—H15A	0.9500
C5—H5A	0.9500	C16—C17	1.353 (3)
C7—C8	1.510 (2)	C16—H16A	0.9500
C8—C9	1.506 (2)	C17—C18	1.418 (2)
C8—H8A	0.9900	C17—H17A	0.9500
C8—H8B	0.9900
C7—N1—C6	126.36 (13)	C10—C9—C18	119.18 (14)
C7—N1—H1N	117.4 (12)	C10—C9—C8	120.38 (15)
C6—N1—H1N	116.2 (12)	C18—C9—C8	120.41 (14)
C2—C1—C6	119.32 (14)	C9—C10—C11	121.43 (18)
C2—C1—H1B	120.3	C9—C10—H10A	119.3
C6—C1—H1B	120.3	C11—C10—H10A	119.3
C1—C2—C3	119.85 (15)	C12—C11—C10	120.37 (17)
C1—C2—Cl1	119.47 (13)	C12—C11—H11A	119.8
C3—C2—Cl1	120.68 (13)	C10—C11—H11A	119.8
F1—C3—C4	119.05 (15)	C11—C12—C13	120.77 (16)
F1—C3—C2	119.71 (15)	C11—C12—H12A	119.6
C4—C3—C2	121.24 (15)	C13—C12—H12A	119.6
C3—C4—C5	119.37 (15)	C14—C13—C12	122.34 (17)
C3—C4—H4A	120.3	C14—C13—C18	118.60 (17)
C5—C4—H4A	120.3	C12—C13—C18	119.06 (17)
C4—C5—C6	119.90 (14)	C15—C14—C13	121.24 (18)
C4—C5—H5A	120.0	C15—C14—H14A	119.4
C6—C5—H5A	120.0	C13—C14—H14A	119.4
C1—C6—C5	120.32 (14)	C14—C15—C16	120.3 (2)
C1—C6—N1	117.00 (13)	C14—C15—H15A	119.8
C5—C6—N1	122.56 (14)	C16—C15—H15A	119.8
O1—C7—N1	123.71 (15)	C17—C16—C15	120.9 (2)
O1—C7—C8	122.22 (14)	C17—C16—H16A	119.5
N1—C7—C8	114.01 (13)	C15—C16—H16A	119.5
C9—C8—C7	112.03 (13)	C16—C17—C18	120.59 (17)
C9—C8—H8A	109.2	C16—C17—H17A	119.7
C7—C8—H8A	109.2	C18—C17—H17A	119.7
C9—C8—H8B	109.2	C9—C18—C17	122.51 (14)
C7—C8—H8B	109.2	C9—C18—C13	119.17 (15)
H8A—C8—H8B	107.9	C17—C18—C13	118.31 (16)
C6—C1—C2—C3	0.3 (2)	C18—C9—C10—C11	−1.2 (2)
C6—C1—C2—Cl1	−179.17 (11)	C8—C9—C10—C11	176.99 (15)
C1—C2—C3—F1	178.93 (14)	C9—C10—C11—C12	0.1 (3)
Cl1—C2—C3—F1	−1.6 (2)	C10—C11—C12—C13	1.1 (3)
C1—C2—C3—C4	−0.8 (2)	C11—C12—C13—C14	178.56 (17)
Cl1—C2—C3—C4	178.65 (13)	C11—C12—C13—C18	−1.1 (2)
F1—C3—C4—C5	−179.02 (14)	C12—C13—C14—C15	−178.31 (18)
C2—C3—C4—C5	0.7 (2)	C18—C13—C14—C15	1.4 (3)
C3—C4—C5—C6	−0.1 (2)	C13—C14—C15—C16	−0.6 (3)
C2—C1—C6—C5	0.3 (2)	C14—C15—C16—C17	−0.8 (3)
C2—C1—C6—N1	−175.86 (14)	C15—C16—C17—C18	1.3 (3)
C4—C5—C6—C1	−0.4 (2)	C10—C9—C18—C17	−177.71 (15)
C4—C5—C6—N1	175.56 (14)	C8—C9—C18—C17	4.1 (2)
C7—N1—C6—C1	−150.76 (15)	C10—C9—C18—C13	1.2 (2)
C7—N1—C6—C5	33.2 (2)	C8—C9—C18—C13	−177.05 (13)
C6—N1—C7—O1	6.9 (3)	C16—C17—C18—C9	178.35 (17)
C6—N1—C7—C8	−170.51 (14)	C16—C17—C18—C13	−0.5 (2)
O1—C7—C8—C9	33.6 (2)	C14—C13—C18—C9	−179.71 (15)
N1—C7—C8—C9	−148.94 (14)	C12—C13—C18—C9	0.0 (2)
C7—C8—C9—C10	−100.15 (18)	C14—C13—C18—C17	−0.8 (2)
C7—C8—C9—C18	78.05 (18)	C12—C13—C18—C17	178.91 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (1)	2.12 (2)	2.914 (2)	157.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (1)	2.12 (2)	2.914 (2)	157 (2)

Symmetry code: (i) .