N-(4-Chloro­phen­yl)benzamide

Gowda, B.T.; Tokarčík, M.; Kožíšek, J.; Sowmya, B.P.; Fuess, H.

doi:10.1107/S1600536808008155

organic compounds

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Volume 64| Part 4| April 2008| Page o769

doi:10.1107/S1600536808008155

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N-(4-Chlorophenyl)benzamide

B. Thimme Gowda,^a ^* Miroslav Tokarčík,^b Jozef Kožíšek,^b B. P. Sowmya ^a and Hartmut Fuess ^c

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bFaculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and ^cInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, Darmstadt, D-64287, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 20 March 2008; accepted 26 March 2008; online 29 March 2008)

The structure of the title compound, C₁₃H₁₀ClNO, resembles those of N-phenylbenzamide, N-(2-chlorophenyl)benzamide and other benzanilides, with similar bond parameters. The amide group –NHCO– makes a dihedral angle of 29.95 (9)° with the benzoyl ring, while the benzoyl and aniline rings form a dihedral angle of 60.76 (3)°. The structure shows both intra- and intermolecular hydrogen bonding. The molecules are linked by N—H⋯O hydrogen bonds into chains running along the [100] direction.

Related literature

For related literature, see: Gowda et al. (2003 , 2007 , 2008 ).

Experimental

Crystal data

C₁₃H₁₀ClNO
M_r = 231.67
Triclinic, $[P \overline 1]$
a = 5.3789 (1) Å
b = 7.8501 (2) Å
c = 13.6318 (4) Å
α = 106.509 (2)°
β = 98.380 (2)°
γ = 90.631 (2)°
V = 545.15 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 295 (2) K
0.52 × 0.25 × 0.08 mm

Data collection

Oxford Xcalibur diffractometer
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ), using a multifaceted crystal model based on expressions derived by Clark & Reid (1995 )] T_min = 0.852, T_max = 0.975
23656 measured reflections
2087 independent reflections
1773 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.091
S = 1.08
2087 reflections
148 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1	0.93	2.43	2.9090 (17)	112
N1—H1N⋯O1ⁱ	0.845 (16)	2.390 (16)	3.1710 (15)	154.0 (15)
C13—H13⋯O1ⁱ	0.93	2.58	3.2507 (11)	129
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008155/dn2327sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008155/dn2327Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of N-(4-chlorophenyl)benzamide (N4CPBA) has been determined to study the effect of substituents on the structures of benzanilides (Gowda et al., 2003, 2007, 2008).

The structure of N4CPBA (Fig.1) is similar to those of N-(phenyl)benzamide, N-(2-chlorophenyl)benzamide, N-(3-chlorophenyl)benzamide and N-(4-methylphenyl)benzamide and other benzanilides (Gowda et al., 2003, 2007, 2008). The amide group –NHCO– forms dihedral angle of 29.95 (9)° with the benzoyl ring, while the two benzene rings (benzoyl and aniline rings) form dihedral angle of 60.76 (3)°. Part of the structure of N4CPBA as viewed down the b axis and showing infinite molecular chains in the [100] direction is shown in Fig. 2. The chains are generated by the intermolecular N—H···O hydrogen bonds (Table 1).

Related literature top

For related literature, see: Gowda et al. (2003, 2007, 2008).

Experimental top

The title compound was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii. Intramolecular hydrogen bond C9—H9···O1 is shown by dashed line.
	Fig. 2. Part of the crystal structure of the title compound viewed down the b axis and showing infinite molecular chains in the[100] direction. H atoms not involved in intermolecular bonding have been omitted. [Symmetry code: (i) x + 1, y, z]

N-(4-Chlorophenyl)-benzamide top

Crystal data top

C₁₃H₁₀ClNO	Z = 2
M_r = 231.67	F(000) = 240
Triclinic, P1	D_x = 1.411 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3789 (1) Å	Cell parameters from 13860 reflections
b = 7.8501 (2) Å	θ = 3.1–29.3°
c = 13.6318 (4) Å	µ = 0.33 mm⁻¹
α = 106.509 (2)°	T = 295 K
β = 98.380 (2)°	Block, colorless
γ = 90.631 (2)°	0.52 × 0.25 × 0.08 mm
V = 545.15 (2) Å³

Data collection top

Oxford Xcalibur diffractometer	2087 independent reflections
Radiation source: fine-focus sealed tube	1773 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 10.434 pixels mm^-1	θ_max = 25.8°, θ_min = 5.6°
ϕ scans, and ω scans with κ offsets	h = −6→6
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2007). Analytical absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]	k = −9→9
T_min = 0.852, T_max = 0.975	l = −16→16
23656 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0494P)² + 0.0939P] where P = (F_o² + 2F_c²)/3
2087 reflections	(Δ/σ)_max = 0.001
148 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₃H₁₀ClNO	γ = 90.631 (2)°
M_r = 231.67	V = 545.15 (2) Å³
Triclinic, P1	Z = 2
a = 5.3789 (1) Å	Mo Kα radiation
b = 7.8501 (2) Å	µ = 0.33 mm⁻¹
c = 13.6318 (4) Å	T = 295 K
α = 106.509 (2)°	0.52 × 0.25 × 0.08 mm
β = 98.380 (2)°

Data collection top

Oxford Xcalibur diffractometer	2087 independent reflections
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2007). Analytical absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]	1773 reflections with I > 2σ(I)
T_min = 0.852, T_max = 0.975	R_int = 0.026
23656 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	1 restraint
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.19 e Å⁻³
2087 reflections	Δρ_min = −0.23 e Å⁻³
148 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	0.3126 (2)	0.77177 (16)	0.02982 (9)	0.0381 (3)
H1N	0.443 (3)	0.757 (2)	0.0010 (13)	0.046*
O1	−0.11350 (19)	0.74813 (17)	0.00041 (8)	0.0563 (3)
C1	0.0870 (2)	0.71549 (18)	−0.03078 (10)	0.0370 (3)
C2	0.0976 (2)	0.61312 (17)	−0.14032 (10)	0.0343 (3)
C3	−0.1018 (2)	0.62387 (19)	−0.21496 (11)	0.0396 (3)
H3	−0.2346	0.6941	−0.1956	0.047*
C4	−0.1045 (3)	0.5314 (2)	−0.31747 (11)	0.0450 (3)
H4	−0.2376	0.5409	−0.3671	0.054*
C5	0.0893 (3)	0.4249 (2)	−0.34662 (11)	0.0460 (4)
H5	0.0871	0.3621	−0.4158	0.055*
C6	0.2867 (3)	0.41171 (19)	−0.27281 (12)	0.0452 (3)
H6	0.4167	0.3387	−0.2924	0.054*
C7	0.2930 (3)	0.50593 (18)	−0.17026 (11)	0.0392 (3)
H7	0.4281	0.4977	−0.1211	0.047*
C8	0.3531 (2)	0.87653 (17)	0.13439 (10)	0.0337 (3)
C9	0.1943 (3)	0.86476 (19)	0.20396 (10)	0.0396 (3)
H9	0.0509	0.7884	0.1818	0.048*
C10	0.2490 (3)	0.96646 (19)	0.30619 (11)	0.0415 (3)
H10	0.1426	0.9588	0.353	0.05*
C11	0.4617 (3)	1.07920 (18)	0.33843 (10)	0.0396 (3)
C12	0.6211 (3)	1.09201 (19)	0.27047 (11)	0.0419 (3)
H12	0.7643	1.1685	0.293	0.05*
C13	0.56679 (8)	0.99040 (5)	0.16848 (3)	0.0391 (3)
H13	0.6744	0.9983	0.1222	0.047*
Cl1	0.53006 (8)	1.20876 (5)	0.46690 (3)	0.06227 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0320 (6)	0.0455 (7)	0.0326 (6)	0.0003 (5)	0.0068 (5)	0.0037 (5)
O1	0.0336 (5)	0.0849 (8)	0.0394 (6)	0.0060 (5)	0.0073 (4)	−0.0005 (5)
C1	0.0337 (7)	0.0404 (7)	0.0347 (7)	0.0024 (5)	0.0045 (5)	0.0076 (6)
C2	0.0328 (7)	0.0340 (7)	0.0345 (7)	−0.0022 (5)	0.0060 (5)	0.0069 (5)
C3	0.0328 (7)	0.0422 (7)	0.0400 (7)	0.0032 (5)	0.0043 (5)	0.0066 (6)
C4	0.0402 (8)	0.0505 (8)	0.0379 (7)	−0.0029 (6)	−0.0035 (6)	0.0075 (6)
C5	0.0487 (8)	0.0474 (8)	0.0342 (7)	−0.0054 (6)	0.0074 (6)	−0.0009 (6)
C6	0.0394 (8)	0.0436 (8)	0.0471 (8)	0.0043 (6)	0.0117 (6)	0.0020 (6)
C7	0.0335 (7)	0.0412 (7)	0.0394 (7)	0.0023 (5)	0.0026 (5)	0.0077 (6)
C8	0.0325 (6)	0.0343 (7)	0.0323 (6)	0.0043 (5)	0.0039 (5)	0.0067 (5)
C9	0.0343 (7)	0.0451 (8)	0.0369 (7)	−0.0042 (6)	0.0026 (5)	0.0097 (6)
C10	0.0404 (7)	0.0510 (8)	0.0333 (7)	0.0031 (6)	0.0084 (6)	0.0113 (6)
C11	0.0442 (8)	0.0378 (7)	0.0317 (7)	0.0065 (6)	0.0004 (6)	0.0043 (5)
C12	0.0369 (7)	0.0385 (7)	0.0441 (8)	−0.0035 (6)	0.0005 (6)	0.0051 (6)
C13	0.0347 (7)	0.0416 (7)	0.0401 (7)	0.0007 (5)	0.0091 (6)	0.0089 (6)
Cl1	0.0764 (3)	0.0615 (3)	0.0352 (2)	−0.0009 (2)	−0.00138 (18)	−0.00280 (18)

Geometric parameters (Å, º) top

N1—C1	1.3560 (18)	C6—H6	0.93
N1—C8	1.4125 (17)	C7—H7	0.93
N1—H1N	0.845 (16)	C8—C13	1.3862 (13)
O1—C1	1.2196 (16)	C8—C9	1.3862 (18)
C1—C2	1.4909 (18)	C9—C10	1.3817 (19)
C2—C3	1.3876 (19)	C9—H9	0.93
C2—C7	1.3885 (19)	C10—C11	1.377 (2)
C3—C4	1.377 (2)	C10—H10	0.93
C3—H3	0.93	C11—C12	1.373 (2)
C4—C5	1.376 (2)	C11—Cl1	1.7402 (14)
C4—H4	0.93	C12—C13	1.3786 (15)
C5—C6	1.379 (2)	C12—H12	0.93
C5—H5	0.93	C13—H13	0.93
C6—C7	1.379 (2)

C1—N1—C8	126.64 (11)	C6—C7—C2	120.02 (13)
C1—N1—H1N	117.7 (11)	C6—C7—H7	120
C8—N1—H1N	115.0 (12)	C2—C7—H7	120
O1—C1—N1	123.02 (12)	C13—C8—C9	119.42 (11)
O1—C1—C2	121.31 (12)	C13—C8—N1	117.74 (10)
N1—C1—C2	115.66 (11)	C9—C8—N1	122.80 (12)
C3—C2—C7	119.04 (12)	C10—C9—C8	120.05 (12)
C3—C2—C1	117.62 (11)	C10—C9—H9	120
C7—C2—C1	123.33 (12)	C8—C9—H9	120
C4—C3—C2	120.51 (12)	C11—C10—C9	119.65 (12)
C4—C3—H3	119.7	C11—C10—H10	120.2
C2—C3—H3	119.7	C9—C10—H10	120.2
C5—C4—C3	120.17 (13)	C12—C11—C10	120.97 (13)
C5—C4—H4	119.9	C12—C11—Cl1	119.21 (11)
C3—C4—H4	119.9	C10—C11—Cl1	119.82 (11)
C4—C5—C6	119.71 (13)	C11—C12—C13	119.40 (12)
C4—C5—H5	120.1	C11—C12—H12	120.3
C6—C5—H5	120.1	C13—C12—H12	120.3
C7—C6—C5	120.53 (13)	C12—C13—C8	120.52 (9)
C7—C6—H6	119.7	C12—C13—H13	119.7
C5—C6—H6	119.7	C8—C13—H13	119.7

C8—N1—C1—O1	−1.4 (2)	C1—C2—C7—C6	178.39 (12)
C8—N1—C1—C2	177.27 (12)	C1—N1—C8—C13	−149.06 (12)
O1—C1—C2—C3	28.33 (19)	C1—N1—C8—C9	33.4 (2)
N1—C1—C2—C3	−150.35 (12)	C13—C8—C9—C10	0.24 (18)
O1—C1—C2—C7	−150.27 (14)	N1—C8—C9—C10	177.75 (12)
N1—C1—C2—C7	31.06 (18)	C8—C9—C10—C11	0.0 (2)
C7—C2—C3—C4	−0.8 (2)	C9—C10—C11—C12	−0.1 (2)
C1—C2—C3—C4	−179.47 (12)	C9—C10—C11—Cl1	179.53 (10)
C2—C3—C4—C5	1.0 (2)	C10—C11—C12—C13	0.0 (2)
C3—C4—C5—C6	−0.3 (2)	Cl1—C11—C12—C13	−179.61 (9)
C4—C5—C6—C7	−0.7 (2)	C11—C12—C13—C8	0.18 (17)
C5—C6—C7—C2	1.0 (2)	C9—C8—C13—C12	−0.32 (15)
C3—C2—C7—C6	−0.2 (2)	N1—C8—C13—C12	−177.95 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.93	2.43	2.9090 (17)	112
N1—H1N···O1ⁱ	0.85 (2)	2.39 (2)	3.1710 (15)	154 (2)
C13—H13···O1ⁱ	0.93	2.58	3.2507 (11)	129

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀ClNO
M_r	231.67
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	5.3789 (1), 7.8501 (2), 13.6318 (4)
α, β, γ (°)	106.509 (2), 98.380 (2), 90.631 (2)
V (Å³)	545.15 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.52 × 0.25 × 0.08

Data collection
Diffractometer	Oxford Xcalibur diffractometer
Absorption correction	Analytical [CrysAlis RED (Oxford Diffraction, 2007). Analytical absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.852, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	23656, 2087, 1773
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.613

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.091, 1.08
No. of reflections	2087
No. of parameters	148
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.23

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.93	2.43	2.9090 (17)	111.9
N1—H1N···O1ⁱ	0.845 (16)	2.390 (16)	3.1710 (15)	154.0 (15)
C13—H13···O1ⁱ	0.93	2.58	3.2507 (11)	129.3

Symmetry code: (i) x+1, y, z.

Acknowledgements

MT and JK thank the Grant Agency of the Slovak Republic (grant No. VEGA 1/0817/08) and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

References

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