4-Chloro-N-phenyl­benzamide

Rodrigues, V.Z.; Kucková, L.; Gowda, B.T.; Kožíšek, J.

doi:10.1107/S1600536811045107

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3171

https://doi.org/10.1107/S1600536811045107

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4-Chloro-N-phenylbenzamide

Vinola Z. Rodrigues,^a Lenka Kucková,^b B. Thimme Gowda ^a ^* and Jozef Kožíšek ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 26 October 2011; accepted 27 October 2011; online 5 November 2011)

In the title compound, C₁₃H₁₀ClNO, the dihedral angle between the two benzene rings is 59.6 (1)°. The crystal structure features N—H⋯O hydrogen bonds, which link the molecules into C(4) chains running along the a axis.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bhat & Gowda (2000 ); Bowes et al. (2003 ); Gowda et al. (2008 ); Saeed et al. (2010 ), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ), on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005 ) and on N-chloro-amides, Gowda & Weiss (1994 ).

Experimental

Crystal data

C₁₃H₁₀ClNO
M_r = 231.67
Triclinic, $[P \overline 1]$
a = 5.3934 (3) Å
b = 7.7679 (5) Å
c = 13.7831 (8) Å
α = 105.887 (5)°
β = 100.849 (4)°
γ = 90.023 (4)°
V = 544.64 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 298 K
0.99 × 0.51 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ), based on expressions derived by Clark & Reid (1995 )] T_min = 0.821, T_max = 0.953
8972 measured reflections
3010 independent reflections
2330 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.115
S = 1.07
3010 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.39	3.1987 (16)	157
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811045107/bt5692sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045107/bt5692Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811045107/bt5692Isup3.cml

checkCIF report

Comment top

The amide moiety is the constituent of many biologically significant compounds. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bhat & Gowda, 2000; Bowes et al., 2003; Gowda et al., 2008; Saeed et al., 2010, N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005) and N-chloro-arylamides (Gowda & Weiss, 1994), in the present work, the crystal structure of N-(phenyl)-4-chlorobenzamide (I) has been determined (Fig.1).

In (I), the N—H and C=O bonds in the C—NH—C(O)—C segment are anti to each other, similar to that observed in N-(4-chlorophenyl)-benzamide (II)(Gowda et al., 2008).

The dihedral angle between the two benzene rings is 59.6 (1)°, compared to the value of 60.8 (1)° in (II).

The packing of molecules linked by N—H···O hydrogen bonds into infinite chains is shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Gowda et al. (2003). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bhat & Gowda (2000); Bowes et al. (2003); Gowda et al. (2008); Saeed et al. (2010), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007), on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005) and on N-chloro-amides, Gowda & Weiss (1994).

Experimental top

The title compound was prepared according to the method described by 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. Rod-like colourless single crystals of the title compound were obtained by slow evaporation from an ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.

Structure description top

In (I), the N—H and C=O bonds in the C—NH—C(O)—C segment are anti to each other, similar to that observed in N-(4-chlorophenyl)-benzamide (II)(Gowda et al., 2008).

The dihedral angle between the two benzene rings is 59.6 (1)°, compared to the value of 60.8 (1)° in (II).

The packing of molecules linked by N—H···O hydrogen bonds into infinite chains is shown in Fig. 2.

For the preparation of the title compound, see: Gowda et al. (2003). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bhat & Gowda (2000); Bowes et al. (2003); Gowda et al. (2008); Saeed et al. (2010), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007), on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005) and on N-chloro-amides, Gowda & Weiss (1994).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2002); software used to prepare material for publication: enCIFer (Allen et al., 2004).

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.
	Fig. 2. Part of the crystal structure of the title compound. Molecular chains are generated by N—H···O hydrogen bonds which are shown by dashed lines.

4-Chloro-N-phenylbenzamide top

Crystal data top

C₁₃H₁₀ClNO	Z = 2
M_r = 231.67	F(000) = 240
Triclinic, P1	D_x = 1.413 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3934 (3) Å	Cell parameters from 3954 reflections
b = 7.7679 (5) Å	θ = 3.5–29.4°
c = 13.7831 (8) Å	µ = 0.33 mm⁻¹
α = 105.887 (5)°	T = 298 K
β = 100.849 (4)°	Plate, colourless
γ = 90.023 (4)°	0.99 × 0.51 × 0.15 mm
V = 544.64 (5) Å³

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3010 independent reflections
Radiation source: fine-focus sealed tube	2330 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
Detector resolution: 10.4340 pixels mm^-1	θ_max = 29.4°, θ_min = 3.5°
ω scans	h = −7→7
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	k = −10→10
T_min = 0.821, T_max = 0.953	l = −18→18
8972 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0498P)² + 0.2195P] where P = (F_o² + 2F_c²)/3
3010 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₃H₁₀ClNO	γ = 90.023 (4)°
M_r = 231.67	V = 544.64 (5) Å³
Triclinic, P1	Z = 2
a = 5.3934 (3) Å	Mo Kα radiation
b = 7.7679 (5) Å	µ = 0.33 mm⁻¹
c = 13.7831 (8) Å	T = 298 K
α = 105.887 (5)°	0.99 × 0.51 × 0.15 mm
β = 100.849 (4)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3010 independent reflections
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	2330 reflections with I > 2σ(I)
T_min = 0.821, T_max = 0.953	R_int = 0.013
8972 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.07	Δρ_max = 0.25 e Å⁻³
3010 reflections	Δρ_min = −0.38 e Å⁻³
145 parameters

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived (Clark & Reid, 1995).

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
C1	0.0813 (3)	0.2427 (2)	0.47100 (11)	0.0338 (3)
C2	0.0923 (3)	0.24248 (19)	0.36321 (11)	0.0309 (3)
C3	0.2913 (3)	0.3259 (2)	0.33873 (12)	0.0354 (3)
H3A	0.4279	0.3806	0.3902	0.042*
C4	0.2871 (3)	0.3280 (2)	0.23842 (12)	0.0381 (3)
H4A	0.4191	0.3849	0.2223	0.046*
C5	0.0845 (3)	0.2446 (2)	0.16262 (11)	0.0368 (3)
C6	−0.1146 (3)	0.1601 (2)	0.18473 (12)	0.0394 (3)
H6A	−0.2494	0.1037	0.1328	0.047*
C7	−0.1100 (3)	0.1608 (2)	0.28539 (12)	0.0358 (3)
H7A	−0.2442	0.1058	0.3013	0.043*
C8	0.3529 (3)	0.25180 (19)	0.63918 (11)	0.0302 (3)
C9	0.1937 (3)	0.3348 (2)	0.70443 (11)	0.0352 (3)
H9A	0.0466	0.3833	0.6787	0.042*
C10	0.2563 (3)	0.3443 (2)	0.80795 (12)	0.0397 (3)
H10A	0.1506	0.4001	0.8518	0.048*
C11	0.4737 (3)	0.2720 (2)	0.84716 (12)	0.0421 (4)
H11A	0.5144	0.2794	0.9169	0.050*
C12	0.6304 (3)	0.1886 (2)	0.78171 (13)	0.0410 (4)
H12A	0.7766	0.1392	0.8076	0.049*
C13	0.5711 (3)	0.1780 (2)	0.67819 (12)	0.0352 (3)
H13A	0.6771	0.1216	0.6346	0.042*
N1	0.3086 (2)	0.24555 (17)	0.53357 (9)	0.0340 (3)
H1A	0.4398	0.2433	0.5063	0.041*
O1	−0.1215 (2)	0.2392 (2)	0.49853 (9)	0.0507 (3)
Cl1	0.07987 (11)	0.24911 (8)	0.03678 (3)	0.06247 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0306 (7)	0.0405 (8)	0.0314 (7)	0.0001 (6)	0.0075 (5)	0.0109 (6)
C2	0.0292 (6)	0.0351 (7)	0.0299 (7)	0.0041 (5)	0.0073 (5)	0.0105 (5)
C3	0.0301 (7)	0.0422 (8)	0.0342 (7)	−0.0018 (6)	0.0043 (6)	0.0126 (6)
C4	0.0367 (7)	0.0430 (8)	0.0397 (8)	0.0003 (6)	0.0129 (6)	0.0161 (7)
C5	0.0436 (8)	0.0413 (8)	0.0284 (7)	0.0086 (6)	0.0109 (6)	0.0121 (6)
C6	0.0364 (8)	0.0465 (8)	0.0317 (7)	−0.0011 (6)	0.0025 (6)	0.0080 (6)
C7	0.0294 (7)	0.0439 (8)	0.0347 (7)	−0.0020 (6)	0.0066 (6)	0.0116 (6)
C8	0.0285 (6)	0.0340 (7)	0.0292 (7)	−0.0019 (5)	0.0058 (5)	0.0106 (5)
C9	0.0306 (7)	0.0427 (8)	0.0339 (7)	0.0052 (6)	0.0082 (6)	0.0121 (6)
C10	0.0376 (8)	0.0496 (9)	0.0334 (8)	0.0020 (6)	0.0131 (6)	0.0101 (7)
C11	0.0410 (8)	0.0565 (10)	0.0313 (7)	−0.0044 (7)	0.0053 (6)	0.0177 (7)
C12	0.0319 (7)	0.0517 (9)	0.0427 (9)	0.0034 (6)	0.0031 (6)	0.0217 (7)
C13	0.0301 (7)	0.0414 (8)	0.0368 (8)	0.0041 (6)	0.0095 (6)	0.0132 (6)
N1	0.0285 (6)	0.0470 (7)	0.0293 (6)	0.0034 (5)	0.0081 (5)	0.0135 (5)
O1	0.0287 (5)	0.0897 (10)	0.0361 (6)	−0.0018 (6)	0.0085 (4)	0.0204 (6)
Cl1	0.0798 (4)	0.0789 (4)	0.0331 (2)	0.0003 (3)	0.0155 (2)	0.0199 (2)

Geometric parameters (Å, º) top

C1—O1	1.2257 (17)	C8—C13	1.390 (2)
C1—N1	1.3558 (19)	C8—C9	1.391 (2)
C1—C2	1.4976 (19)	C8—N1	1.4173 (17)
C2—C7	1.389 (2)	C9—C10	1.384 (2)
C2—C3	1.3933 (19)	C9—H9A	0.9300
C3—C4	1.383 (2)	C10—C11	1.382 (2)
C3—H3A	0.9300	C10—H10A	0.9300
C4—C5	1.380 (2)	C11—C12	1.384 (2)
C4—H4A	0.9300	C11—H11A	0.9300
C5—C6	1.382 (2)	C12—C13	1.382 (2)
C5—Cl1	1.7398 (15)	C12—H12A	0.9300
C6—C7	1.382 (2)	C13—H13A	0.9300
C6—H6A	0.9300	N1—H1A	0.8600
C7—H7A	0.9300

O1—C1—N1	123.61 (14)	C13—C8—C9	119.85 (13)
O1—C1—C2	121.13 (13)	C13—C8—N1	117.54 (12)
N1—C1—C2	115.26 (12)	C9—C8—N1	122.54 (13)
C7—C2—C3	119.09 (13)	C10—C9—C8	119.35 (14)
C7—C2—C1	118.05 (12)	C10—C9—H9A	120.3
C3—C2—C1	122.82 (13)	C8—C9—H9A	120.3
C4—C3—C2	120.48 (14)	C11—C10—C9	120.98 (14)
C4—C3—H3A	119.8	C11—C10—H10A	119.5
C2—C3—H3A	119.8	C9—C10—H10A	119.5
C5—C4—C3	119.13 (14)	C10—C11—C12	119.37 (15)
C5—C4—H4A	120.4	C10—C11—H11A	120.3
C3—C4—H4A	120.4	C12—C11—H11A	120.3
C4—C5—C6	121.55 (14)	C13—C12—C11	120.46 (14)
C4—C5—Cl1	118.82 (12)	C13—C12—H12A	119.8
C6—C5—Cl1	119.62 (12)	C11—C12—H12A	119.8
C7—C6—C5	118.82 (14)	C12—C13—C8	119.98 (14)
C7—C6—H6A	120.6	C12—C13—H13A	120.0
C5—C6—H6A	120.6	C8—C13—H13A	120.0
C6—C7—C2	120.92 (13)	C1—N1—C8	126.94 (12)
C6—C7—H7A	119.5	C1—N1—H1A	116.5
C2—C7—H7A	119.5	C8—N1—H1A	116.5

O1—C1—C2—C7	−28.3 (2)	C1—C2—C7—C6	178.28 (14)
N1—C1—C2—C7	151.19 (14)	C13—C8—C9—C10	0.7 (2)
O1—C1—C2—C3	149.28 (16)	N1—C8—C9—C10	−176.47 (14)
N1—C1—C2—C3	−31.2 (2)	C8—C9—C10—C11	−0.3 (2)
C7—C2—C3—C4	0.3 (2)	C9—C10—C11—C12	−0.2 (2)
C1—C2—C3—C4	−177.34 (14)	C10—C11—C12—C13	0.3 (2)
C2—C3—C4—C5	−0.7 (2)	C11—C12—C13—C8	0.1 (2)
C3—C4—C5—C6	0.4 (2)	C9—C8—C13—C12	−0.6 (2)
C3—C4—C5—Cl1	179.60 (12)	N1—C8—C13—C12	176.70 (13)
C4—C5—C6—C7	0.4 (2)	O1—C1—N1—C8	−2.5 (3)
Cl1—C5—C6—C7	−178.78 (12)	C2—C1—N1—C8	177.96 (13)
C5—C6—C7—C2	−0.9 (2)	C13—C8—N1—C1	152.65 (15)
C3—C2—C7—C6	0.6 (2)	C9—C8—N1—C1	−30.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.39	3.1987 (16)	157

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)	298
a, b, c (Å)	5.3934 (3), 7.7679 (5), 13.7831 (8)
α, β, γ (°)	105.887 (5), 100.849 (4), 90.023 (4)
V (Å³)	544.64 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.99 × 0.51 × 0.15

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini
Absorption correction	Analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.821, 0.953
No. of measured, independent and observed [I > 2σ(I)] reflections	8972, 3010, 2330
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.690

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.115, 1.07
No. of reflections	3010
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.38

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2002), enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.39	3.1987 (16)	157.2

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

Acknowledgements

LK and JK thank the Grant Agencies for their financial support (VEGA Grant Agency of Slovak Ministry of Education 1/0679/11; Research and Development Agency of Slovakia (APVV-0202–10) and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer. VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS research fellowship.

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