N-(3-Chloro­phen­yl)benzamide

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

doi:10.1107/S1600536808001311

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o462

doi:10.1107/S1600536808001311

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N-(3-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, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 11 January 2008; accepted 13 January 2008; online 16 January 2008)

The conformation of the N—H bond in the structure of the title compound (N3CPBA), C₁₃H₁₀ClNO, is anti to the meta chloro substituent in the aniline benzene ring, similar to that observed with respect to the ortho chloro substituent in N-(2-chlorophenyl)benzamide (N2CPBA) and meta chloro substituent in N-(3,4-dichlorophenyl)benzamide (N34DCPBA), but in contrast to the syn conformation observed with respect to both the ortho and the meta chloro substituents in N-(2,3-dichlorophenyl)benzamide (N23DCPBA). The bond parameters in N3CPBA are similar to those in N-phenylbenzamide, N2CPBA, N23DCPBA, N34DCPBA and other benzanilides. The amide group –NHCO– makes a dihedral angle of 18.2 (2)° with the benzoyl ring, while the dihedral angle between the two benzene rings is 61.0 (1)°. The molecules are linked into chains along the b axis by N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2003 ); Gowda, Sowmya, Kožíšek et al. (2007 ); Gowda, Sowmya, Tokarčík et al. (2007 ).

Experimental

Crystal data

C₁₃H₁₀ClNO
M_r = 231.67
Orthorhombic, P b c a
a = 9.3585 (2) Å
b = 9.7851 (2) Å
c = 25.1419 (6) Å
V = 2302.34 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 295 (2) K
0.41 × 0.13 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ). Analytical numeric absorption correction using a multifaceted crystal model (Clark & Reid, 1995 ). T_min = 0.915, T_max = 0.984
53566 measured reflections
2252 independent reflections
1639 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.101
S = 1.08
2252 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 = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.834 (16)	2.089 (17)	2.8989 (17)	163.5 (17)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

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/S1600536808001311/dn2311sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808001311/dn2311Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of N-(3-chlorophenyl)-benzamide (N3CPBA) has been determined to explore the effect of substituents on the structure of N-aromatic amides (Gowda et al., 2003; Gowda, Sowmya, Kožíšek et al., 2007; Gowda, Sowmya, Tokarčík et al., 2007). The conformation of the N—H bond in the structure of N3CPBA(Fig.1) is anti to the meta chloro substituent in the aniline phenyl ring, similar to that observed with respect to the ortho-chloro substituent in N-(2-chlorophenyl)-benzamide (N2CPBA)(Gowda, Sowmya, Kožíšek et al., 2007) and meta-chloro substituent in N-(3,4-dichlorophenyl)-benzamide (N34DCPBA) (Gowda, Sowmya, Tokarčík et al., 2007), but in contrast to the syn conformation observed with respect to both the ortho & meta-Chloro substituents in N-(2,3-dichlorophenyl)- benzamide (N23DCPBA)(Gowda, Sowmya, Tokarčík et al., 2007). The bond parameters in N3CPBA are similar to those in N-(phenyl)-benzamide, N2CPBA, N23DCPBA, N34DCPBA and other benzanilides. The amide group –NHCO– has the dihedral angle of 18.2 (2)° with the benzoyl ring, while the dihedral angle between the two benzene rings (benzoyl and aniline) is 61.0 (1)°. One-dimensional chains of the title compound along the base vector [0 1 0] formed by hydrogen bonds N1–H1N···O1 (Table 1) as viewed down the a axis is shown in Fig.2.

Related literature top

For related literature, see: Gowda et al. (2003); Gowda, Sowmya, Kožíšek et al. (2007); Gowda, Sowmya, Tokarčík et al. (2007).

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.
	Fig. 2. Crystal structure of the title compound viewed down the axis a. One-dimensional chains along the base vector [0 1 0] are formed by hydrogen bonds N1–H1N···O1(i). H atoms not involved in hydrogen bonding are omitted. [Symmetry code: (i) -x + 1/2, y - 1/2, z]

N-(3-Chlorophenyl)benzamide top

Crystal data top

C₁₃H₁₀ClNO	F(000) = 960
M_r = 231.67	D_x = 1.337 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 14003 reflections
a = 9.3585 (2) Å	θ = 3.0–29.5°
b = 9.7851 (2) Å	µ = 0.31 mm⁻¹
c = 25.1419 (6) Å	T = 295 K
V = 2302.34 (9) Å³	Prism, colourless
Z = 8	0.41 × 0.13 × 0.06 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	2252 independent reflections
Graphite monochromator	1639 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm^-1	R_int = 0.047
ϕ scans, and ω scans with κ offsets	θ_max = 26.0°, θ_min = 4.7°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007). Analytical numeric absorption correction using a multifaceted crystal model (Clark & Reid, 1995).	h = −11→11
T_min = 0.915, T_max = 0.984	k = −12→12
53566 measured reflections	l = −31→31

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0491P)² + 0.2808P] where P = (F_o² + 2F_c²)/3
2252 reflections	(Δ/σ)_max < 0.001
148 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₃H₁₀ClNO	V = 2302.34 (9) Å³
M_r = 231.67	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.3585 (2) Å	µ = 0.31 mm⁻¹
b = 9.7851 (2) Å	T = 295 K
c = 25.1419 (6) Å	0.41 × 0.13 × 0.06 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	2252 independent reflections
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007). Analytical numeric absorption correction using a multifaceted crystal model (Clark & Reid, 1995).	1639 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.984	R_int = 0.047
53566 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.19 e Å⁻³
2252 reflections	Δρ_min = −0.25 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	0.27214 (14)	0.48267 (13)	0.12047 (5)	0.0462 (4)
H1N	0.2650 (19)	0.4004 (17)	0.1287 (6)	0.055*
O1	0.19225 (12)	0.69327 (10)	0.14128 (5)	0.0565 (3)
Cl1	0.54083 (6)	0.81350 (6)	−0.00120 (2)	0.0875 (2)
C1	0.17675 (16)	0.56906 (15)	0.14234 (6)	0.0405 (4)
C2	0.05098 (15)	0.50735 (14)	0.16988 (6)	0.0392 (4)
C3	−0.02405 (19)	0.58822 (17)	0.20536 (7)	0.0546 (5)
H3	0.0038	0.6784	0.2108	0.065*
C4	−0.1391 (2)	0.53666 (19)	0.23252 (8)	0.0671 (5)
H4	−0.1877	0.5916	0.2567	0.081*
C5	−0.1830 (2)	0.4050 (2)	0.22432 (8)	0.0684 (6)
H5	−0.2613	0.3706	0.2427	0.082*
C6	−0.1111 (2)	0.32411 (18)	0.18890 (8)	0.0654 (5)
H6	−0.1414	0.2349	0.1829	0.079*
C7	0.00613 (18)	0.37454 (17)	0.16203 (7)	0.0519 (4)
H7	0.0553	0.3185	0.1384	0.062*
C8	0.40219 (17)	0.52388 (15)	0.09631 (6)	0.0444 (4)
C9	0.40661 (17)	0.63258 (16)	0.06157 (6)	0.0471 (4)
H9	0.3235	0.6796	0.0528	0.056*
C10	0.53533 (19)	0.67062 (18)	0.04005 (7)	0.0544 (5)
C11	0.6590 (2)	0.6017 (2)	0.05099 (8)	0.0719 (6)
H11	0.7453	0.6288	0.0359	0.086*
C12	0.6527 (2)	0.4918 (2)	0.08464 (10)	0.0808 (6)
H12	0.7355	0.4428	0.092	0.097*
C13	0.5255 (2)	0.4528 (2)	0.10771 (8)	0.0657 (5)
H13	0.523	0.3788	0.1309	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0440 (8)	0.0309 (6)	0.0636 (9)	0.0007 (6)	0.0069 (7)	0.0025 (6)
O1	0.0570 (7)	0.0299 (6)	0.0827 (8)	−0.0007 (5)	0.0119 (6)	0.0004 (5)
Cl1	0.0668 (4)	0.0990 (5)	0.0968 (4)	−0.0134 (3)	0.0102 (3)	0.0423 (3)
C1	0.0405 (9)	0.0349 (8)	0.0462 (9)	0.0023 (7)	−0.0054 (7)	0.0006 (7)
C2	0.0387 (8)	0.0353 (8)	0.0437 (8)	0.0030 (6)	−0.0031 (7)	0.0027 (6)
C3	0.0621 (11)	0.0407 (9)	0.0609 (10)	0.0035 (8)	0.0091 (9)	−0.0026 (8)
C4	0.0711 (13)	0.0596 (11)	0.0707 (12)	0.0091 (10)	0.0291 (11)	0.0013 (9)
C5	0.0605 (12)	0.0658 (12)	0.0789 (13)	−0.0021 (10)	0.0232 (11)	0.0136 (10)
C6	0.0615 (12)	0.0485 (10)	0.0862 (14)	−0.0122 (9)	0.0123 (11)	0.0001 (9)
C7	0.0495 (10)	0.0433 (9)	0.0628 (11)	−0.0030 (8)	0.0084 (8)	−0.0081 (8)
C8	0.0418 (9)	0.0393 (8)	0.0521 (9)	0.0005 (7)	0.0040 (7)	−0.0044 (7)
C9	0.0392 (9)	0.0500 (9)	0.0520 (9)	−0.0007 (8)	−0.0016 (8)	−0.0003 (8)
C10	0.0489 (11)	0.0621 (11)	0.0521 (10)	−0.0090 (8)	0.0025 (8)	0.0038 (8)
C11	0.0435 (11)	0.0900 (14)	0.0824 (14)	−0.0024 (10)	0.0133 (10)	0.0107 (12)
C12	0.0461 (12)	0.0917 (15)	0.1046 (16)	0.0207 (11)	0.0101 (11)	0.0216 (13)
C13	0.0528 (12)	0.0615 (11)	0.0827 (13)	0.0112 (9)	0.0081 (10)	0.0170 (10)

Geometric parameters (Å, º) top

N1—C1	1.3468 (19)	C6—C7	1.380 (2)
N1—C8	1.419 (2)	C6—H6	0.93
N1—H1N	0.834 (16)	C7—H7	0.93
O1—C1	1.2244 (17)	C8—C9	1.377 (2)
Cl1—C10	1.7415 (18)	C8—C13	1.378 (2)
C1—C2	1.493 (2)	C9—C10	1.372 (2)
C2—C7	1.380 (2)	C9—H9	0.93
C2—C3	1.384 (2)	C10—C11	1.368 (3)
C3—C4	1.371 (2)	C11—C12	1.369 (3)
C3—H3	0.93	C11—H11	0.93
C4—C5	1.368 (3)	C12—C13	1.378 (3)
C4—H4	0.93	C12—H12	0.93
C5—C6	1.368 (3)	C13—H13	0.93
C5—H5	0.93

C1—N1—C8	124.41 (13)	C2—C7—C6	120.57 (16)
C1—N1—H1N	116.9 (12)	C2—C7—H7	119.7
C8—N1—H1N	116.7 (12)	C6—C7—H7	119.7
O1—C1—N1	122.38 (14)	C9—C8—C13	119.78 (15)
O1—C1—C2	120.33 (14)	C9—C8—N1	121.12 (14)
N1—C1—C2	117.26 (13)	C13—C8—N1	119.10 (14)
C7—C2—C3	118.46 (15)	C10—C9—C8	119.09 (15)
C7—C2—C1	123.66 (14)	C10—C9—H9	120.5
C3—C2—C1	117.88 (13)	C8—C9—H9	120.5
C4—C3—C2	120.60 (16)	C11—C10—C9	122.00 (17)
C4—C3—H3	119.7	C11—C10—Cl1	119.38 (14)
C2—C3—H3	119.7	C9—C10—Cl1	118.60 (14)
C5—C4—C3	120.47 (17)	C10—C11—C12	118.36 (18)
C5—C4—H4	119.8	C10—C11—H11	120.8
C3—C4—H4	119.8	C12—C11—H11	120.8
C4—C5—C6	119.71 (17)	C11—C12—C13	120.98 (19)
C4—C5—H5	120.1	C11—C12—H12	119.5
C6—C5—H5	120.1	C13—C12—H12	119.5
C5—C6—C7	120.18 (17)	C8—C13—C12	119.76 (18)
C5—C6—H6	119.9	C8—C13—H13	120.1
C7—C6—H6	119.9	C12—C13—H13	120.1

C8—N1—C1—O1	3.0 (2)	C5—C6—C7—C2	−1.0 (3)
C8—N1—C1—C2	−175.25 (14)	C1—N1—C8—C9	−45.2 (2)
O1—C1—C2—C7	163.26 (16)	C1—N1—C8—C13	135.30 (17)
N1—C1—C2—C7	−18.5 (2)	C13—C8—C9—C10	−1.9 (2)
O1—C1—C2—C3	−17.0 (2)	N1—C8—C9—C10	178.61 (14)
N1—C1—C2—C3	161.30 (14)	C8—C9—C10—C11	1.7 (3)
C7—C2—C3—C4	0.8 (3)	C8—C9—C10—Cl1	−176.82 (12)
C1—C2—C3—C4	−178.95 (15)	C9—C10—C11—C12	−0.2 (3)
C2—C3—C4—C5	−1.1 (3)	Cl1—C10—C11—C12	178.29 (17)
C3—C4—C5—C6	0.3 (3)	C10—C11—C12—C13	−1.1 (3)
C4—C5—C6—C7	0.8 (3)	C9—C8—C13—C12	0.6 (3)
C3—C2—C7—C6	0.2 (3)	N1—C8—C13—C12	−179.87 (18)
C1—C2—C7—C6	179.94 (16)	C11—C12—C13—C8	0.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.83 (2)	2.09 (2)	2.8989 (17)	164 (2)

Symmetry code: (i) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀ClNO
M_r	231.67
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	9.3585 (2), 9.7851 (2), 25.1419 (6)
V (Å³)	2302.34 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.41 × 0.13 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2007). Analytical numeric absorption correction using a multifaceted crystal model (Clark & Reid, 1995).
T_min, T_max	0.915, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	53566, 2252, 1639
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.101, 1.08
No. of reflections	2252
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, −0.25

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
N1—H1N···O1ⁱ	0.834 (16)	2.089 (17)	2.8989 (17)	163.5 (17)

Symmetry code: (i) −x+1/2, y−1/2, 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.

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