N-(Naphthalen-1-yl)benzamide.

In the title compound, C(17)H(13)NO, the N-H and C=O bonds are anti with respect to each other. The dihedral angle between the naphthalene ring system and the phenyl ring is 86.63 (5)°. In the crystal, N-H⋯O hydrogen bonds link mol-ecules into chains along [010].

Related literature

For a related structure, see: Zhang et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H13NO

M = 247.28

Orthorhombic,

a = 8.2630 (8) Å

b = 9.3792 (9) Å

c = 33.806 (3) Å

V = 2620.0 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.45 × 0.24 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.966, T max = 0.990

12210 measured reflections

2307 independent reflections

1253 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.129

S = 1.04

2307 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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) I, global. DOI: 10.1107/S1600536811045946/lh5366sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045946/lh5366Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045946/lh5366Isup3.cml

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

C17H13NO	F(000) = 1040
Mr = 247.28	Dx = 1.254 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1469 reflections
a = 8.2630 (8) Å	θ = 2.7–20.5°
b = 9.3792 (9) Å	µ = 0.08 mm−1
c = 33.806 (3) Å	T = 298 K
V = 2620.0 (4) Å3	Prism, colorless
Z = 8	0.45 × 0.24 × 0.13 mm

Bruker SMART CCD diffractometer	2307 independent reflections
Radiation source: fine-focus sealed tube	1253 reflections with I > 2σ(I)
graphite	Rint = 0.086
φ and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→8
Tmin = 0.966, Tmax = 0.990	k = −10→11
12210 measured reflections	l = −40→26

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0469P)2] where P = (Fo2 + 2Fc2)/3
2307 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
N1	0.2455 (2)	0.6961 (2)	0.36346 (6)	0.0567 (6)
H1	0.2671	0.7855	0.3655	0.068*
O1	0.3279 (2)	0.48418 (17)	0.33881 (5)	0.0644 (5)
C1	0.3422 (3)	0.6140 (3)	0.34048 (7)	0.0511 (7)
C2	0.4657 (3)	0.6894 (3)	0.31610 (7)	0.0439 (6)
C3	0.5181 (3)	0.6226 (3)	0.28213 (8)	0.0538 (7)
H3	0.4779	0.5330	0.2756	0.065*
C4	0.6293 (3)	0.6871 (3)	0.25781 (8)	0.0650 (8)
H4	0.6620	0.6423	0.2346	0.078*
C5	0.6924 (3)	0.8183 (3)	0.26772 (9)	0.0701 (8)
H5	0.7681	0.8617	0.2513	0.084*
C6	0.6433 (3)	0.8845 (3)	0.30176 (9)	0.0717 (8)
H6	0.6874	0.9722	0.3087	0.086*
C7	0.5284 (3)	0.8213 (3)	0.32578 (8)	0.0602 (7)
H7	0.4933	0.8677	0.3485	0.072*
C8	0.1091 (3)	0.6407 (2)	0.38450 (7)	0.0520 (7)
C9	−0.0404 (4)	0.6895 (3)	0.37506 (8)	0.0648 (8)
H9	−0.0521	0.7592	0.3557	0.078*
C10	−0.1779 (3)	0.6353 (3)	0.39436 (9)	0.0813 (9)
H10	−0.2800	0.6700	0.3880	0.098*
C11	−0.1619 (4)	0.5323 (3)	0.42238 (9)	0.0821 (9)
H11	−0.2536	0.4944	0.4344	0.099*
C12	−0.0082 (3)	0.4827 (3)	0.43327 (8)	0.0628 (8)
C13	0.1314 (3)	0.5404 (2)	0.41501 (7)	0.0516 (7)
C14	0.2849 (3)	0.4941 (3)	0.42846 (8)	0.0630 (8)
H14	0.3783	0.5321	0.4173	0.076*
C15	0.2966 (4)	0.3944 (3)	0.45750 (9)	0.0806 (9)
H15	0.3983	0.3662	0.4663	0.097*
C16	0.1598 (5)	0.3343 (4)	0.47420 (9)	0.0965 (11)
H16	0.1698	0.2635	0.4933	0.116*
C17	0.0127 (5)	0.3784 (3)	0.46272 (9)	0.0897 (10)
H17	−0.0783	0.3388	0.4746	0.108*

	U11	U22	U33	U12	U13	U23
N1	0.0702 (14)	0.0349 (11)	0.0651 (14)	−0.0063 (11)	0.0122 (12)	0.0000 (11)
O1	0.0830 (14)	0.0361 (10)	0.0742 (13)	−0.0041 (9)	0.0132 (10)	0.0025 (10)
C1	0.0635 (18)	0.0372 (15)	0.0526 (16)	0.0037 (14)	−0.0026 (14)	0.0038 (14)
C2	0.0440 (14)	0.0370 (14)	0.0507 (15)	0.0007 (12)	−0.0028 (12)	0.0061 (14)
C3	0.0499 (16)	0.0433 (16)	0.0681 (18)	0.0021 (12)	−0.0011 (14)	−0.0042 (15)
C4	0.0602 (17)	0.0634 (19)	0.0714 (19)	0.0100 (15)	0.0134 (15)	0.0011 (17)
C5	0.0666 (19)	0.0567 (19)	0.087 (2)	−0.0005 (16)	0.0210 (16)	0.0140 (18)
C6	0.076 (2)	0.0451 (16)	0.094 (2)	−0.0135 (15)	0.0137 (17)	−0.0008 (18)
C7	0.0731 (18)	0.0453 (16)	0.0621 (17)	−0.0050 (14)	0.0059 (14)	−0.0019 (15)
C8	0.0624 (18)	0.0399 (14)	0.0538 (16)	0.0019 (13)	0.0041 (14)	−0.0017 (14)
C9	0.0682 (19)	0.0570 (17)	0.0691 (19)	0.0079 (16)	0.0035 (16)	0.0083 (15)
C10	0.061 (2)	0.096 (2)	0.088 (2)	0.0123 (18)	0.0057 (17)	0.006 (2)
C11	0.072 (2)	0.090 (2)	0.084 (2)	−0.0040 (19)	0.0180 (17)	0.012 (2)
C12	0.078 (2)	0.0556 (17)	0.0551 (17)	0.0001 (15)	0.0143 (15)	0.0084 (15)
C13	0.0720 (19)	0.0381 (14)	0.0448 (14)	0.0031 (14)	0.0037 (14)	−0.0027 (13)
C14	0.0745 (19)	0.0567 (18)	0.0577 (18)	0.0079 (15)	0.0008 (15)	0.0013 (15)
C15	0.103 (3)	0.076 (2)	0.0631 (19)	0.0211 (19)	−0.0074 (18)	0.0149 (19)
C16	0.138 (3)	0.085 (2)	0.067 (2)	0.024 (3)	0.015 (2)	0.028 (2)
C17	0.109 (3)	0.083 (2)	0.077 (2)	0.005 (2)	0.0259 (19)	0.020 (2)

N1—C1	1.354 (3)	C8—C13	1.408 (3)
N1—C8	1.431 (3)	C9—C10	1.405 (4)
N1—H1	0.8600	C9—H9	0.9300
O1—C1	1.225 (2)	C10—C11	1.360 (4)
C1—C2	1.490 (3)	C10—H10	0.9300
C2—C3	1.378 (3)	C11—C12	1.402 (4)
C2—C7	1.381 (3)	C11—H11	0.9300
C3—C4	1.373 (3)	C12—C17	1.406 (4)
C3—H3	0.9300	C12—C13	1.415 (3)
C4—C5	1.377 (3)	C13—C14	1.416 (3)
C4—H4	0.9300	C14—C15	1.359 (3)
C5—C6	1.369 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.384 (4)
C6—C7	1.383 (3)	C15—H15	0.9300
C6—H6	0.9300	C16—C17	1.341 (4)
C7—H7	0.9300	C16—H16	0.9300
C8—C9	1.356 (3)	C17—H17	0.9300
C1—N1—C8	122.9 (2)	C8—C9—C10	120.3 (3)
C1—N1—H1	118.5	C8—C9—H9	119.8
C8—N1—H1	118.5	C10—C9—H9	119.8
O1—C1—N1	122.3 (2)	C11—C10—C9	120.2 (3)
O1—C1—C2	120.8 (2)	C11—C10—H10	119.9
N1—C1—C2	116.9 (2)	C9—C10—H10	119.9
C3—C2—C7	119.1 (2)	C10—C11—C12	120.4 (3)
C3—C2—C1	117.4 (2)	C10—C11—H11	119.8
C7—C2—C1	123.4 (2)	C12—C11—H11	119.8
C4—C3—C2	120.6 (2)	C11—C12—C17	121.8 (3)
C4—C3—H3	119.7	C11—C12—C13	119.8 (3)
C2—C3—H3	119.7	C17—C12—C13	118.3 (3)
C3—C4—C5	120.1 (3)	C8—C13—C12	117.9 (2)
C3—C4—H4	120.0	C8—C13—C14	123.9 (2)
C5—C4—H4	120.0	C12—C13—C14	118.2 (2)
C6—C5—C4	119.8 (3)	C15—C14—C13	120.5 (3)
C6—C5—H5	120.1	C15—C14—H14	119.8
C4—C5—H5	120.1	C13—C14—H14	119.8
C5—C6—C7	120.1 (3)	C14—C15—C16	121.1 (3)
C5—C6—H6	119.9	C14—C15—H15	119.4
C7—C6—H6	119.9	C16—C15—H15	119.4
C2—C7—C6	120.2 (2)	C17—C16—C15	119.7 (3)
C2—C7—H7	119.9	C17—C16—H16	120.1
C6—C7—H7	119.9	C15—C16—H16	120.1
C9—C8—C13	121.1 (2)	C16—C17—C12	122.1 (3)
C9—C8—N1	118.6 (2)	C16—C17—H17	119.0
C13—C8—N1	120.2 (2)	C12—C17—H17	119.0
C8—N1—C1—O1	−6.5 (4)	C9—C10—C11—C12	2.2 (4)
C8—N1—C1—C2	171.9 (2)	C10—C11—C12—C17	178.7 (3)
O1—C1—C2—C3	24.1 (3)	C10—C11—C12—C13	0.1 (4)
N1—C1—C2—C3	−154.3 (2)	C9—C8—C13—C12	5.4 (3)
O1—C1—C2—C7	−156.2 (2)	N1—C8—C13—C12	−176.3 (2)
N1—C1—C2—C7	25.4 (3)	C9—C8—C13—C14	−174.6 (2)
C7—C2—C3—C4	−1.1 (3)	N1—C8—C13—C14	3.7 (3)
C1—C2—C3—C4	178.6 (2)	C11—C12—C13—C8	−3.8 (4)
C2—C3—C4—C5	1.6 (4)	C17—C12—C13—C8	177.6 (2)
C3—C4—C5—C6	−0.4 (4)	C11—C12—C13—C14	176.2 (2)
C4—C5—C6—C7	−1.2 (4)	C17—C12—C13—C14	−2.4 (4)
C3—C2—C7—C6	−0.5 (4)	C8—C13—C14—C15	−178.5 (2)
C1—C2—C7—C6	179.8 (2)	C12—C13—C14—C15	1.5 (4)
C5—C6—C7—C2	1.7 (4)	C13—C14—C15—C16	1.0 (4)
C1—N1—C8—C9	−117.0 (3)	C14—C15—C16—C17	−2.6 (5)
C1—N1—C8—C13	64.6 (3)	C15—C16—C17—C12	1.5 (5)
C13—C8—C9—C10	−3.2 (4)	C11—C12—C17—C16	−177.6 (3)
N1—C8—C9—C10	178.4 (2)	C13—C12—C17—C16	1.0 (5)
C8—C9—C10—C11	−0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.21	2.892 (3)	136.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.21	2.892 (3)	136

Symmetry code: (i) .