N-(Naphthalen-1-yl)benzamide

Zhu, R.; Ren, Y.; Li, W.

doi:10.1107/S1600536811045946

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3204

https://doi.org/10.1107/S1600536811045946

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N-(Naphthalen-1-yl)benzamide

Ruitao Zhu,^a ^* Yuehong Ren ^a and Wenjuan Li ^a

^aDepartment of Chemistry, Taiyuan Normal University, Taiyuan 030031, People's Republic of China
^*Correspondence e-mail: ruitaozhu@126.com

(Received 27 October 2011; accepted 1 November 2011; online 5 November 2011)

In the title compound, C₁₇H₁₃NO, 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 molecules 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_r = 247.28
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.056
wR(F²) = 0.129
S = 1.04
2307 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.17 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—H1⋯O1ⁱ	0.86	2.21	2.892 (3)	136
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811045946/lh5366sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045946/lh5366Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811045946/lh5366Isup3.cml

checkCIF report

Comment top

We recently determined the crystal structure of N-(1-naphthyl)benzenesulfonamide (Zhang et al., 2011) and in this paper we present the crystal structure of the title compound (I).

The molecular structure of (I) is shown in Fig. 1. The bond lengths (Allen et al., 1987) and angles are normal. The dihedral angle between the naphthylene ring system and the phenyl ring is 86.63 (5)°. In the crystal, N—H···O hydrogen bonds link molecules into chains along [010] (Fig. 2).

Related literature top

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

Experimental top

To a 100 ml round flask fitted with a condenser was added 1-naphthylamine (1.43 g, 10 mmol), dichloromethane (15 ml) and triethylamine(0.5 ml) with magnetic stirring. Benzoyl chloride (1.16 ml, 10 mmol) was added gradually. The reaction mixture was stirred at room temperature for 1 h and then refluxed for 2 h. The product precipitated as a white powder, which was washed three times with water and dichloromethane. Recrystallization from ethyl alcohol produced the crystals of the title compound.

Structure description top

We recently determined the crystal structure of N-(1-naphthyl)benzenesulfonamide (Zhang et al., 2011) and in this paper we present the crystal structure of the title compound (I).

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

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of (I) with the donor-acceptor distances of hydrogen bonds drawn as dashed lines. H atoms are not shown.

N-(Naphthalen-1-yl)benzamide top

Crystal data top

C₁₇H₁₃NO	F(000) = 1040
M_r = 247.28	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0469P)²] where P = (F_o² + 2F_c²)/3
2307 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₇H₁₃NO	V = 2620.0 (4) Å³
M_r = 247.28	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.2630 (8) Å	µ = 0.08 mm⁻¹
b = 9.3792 (9) Å	T = 298 K
c = 33.806 (3) Å	0.45 × 0.24 × 0.13 mm

Data collection top

Bruker SMART CCD diffractometer	2307 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1253 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.990	R_int = 0.086
12210 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.04	Δρ_max = 0.17 e Å⁻³
2307 reflections	Δρ_min = −0.18 e Å⁻³
172 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃NO
M_r	247.28
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	8.2630 (8), 9.3792 (9), 33.806 (3)
V (Å³)	2620.0 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.24 × 0.13

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.966, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	12210, 2307, 1253
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.129, 1.04
No. of reflections	2307
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.18

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.860	2.214	2.892 (3)	135.61

Symmetry code: (i) −x+1/2, y+1/2, z.

Acknowledgements

The authors gratefully acknowledge the Project of ShanXi scientific and technology (20110321044).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, S., Zhang, Y., Wang, C. & Zhu, R. (2011). Acta Cryst. E67, o2831. Web of Science CSD CrossRef IUCr Journals Google Scholar