2-Chloro-N-(3,5-dichloro­phenyl)­benzamide

Gowda, B.T.; Foro, S.; Sowmya, B.P.; Fuess, H.

doi:10.1107/S1600536808018072

organic compounds

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Volume 64| Part 7| July 2008| Page o1294

doi:10.1107/S1600536808018072

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2-Chloro-N-(3,5-dichlorophenyl)benzamide

B. Thimme Gowda,^a ^* Sabine Foro,^b B. P. Sowmya ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 11 June 2008; accepted 13 June 2008; online 19 June 2008)

The amide group in the structure of the title compound (N35DCP2CBA), C₁₃H₈Cl₃NO, is trans-planar, similar to that observed in N-(3-chlorophenyl)benzamide, N-(3,5-dichlorophenyl)benzamide, 2-chloro-N-phenylbenzamide and other benzanilides. The C=O bond in N35DCP2CBA is anti to the ortho-chloro substituent in the benzoyl ring. The amide group makes dihedral angles of 63.1 (12) and 31.1 (17)°, respectively, with the benzoyl and aniline benzene rings, while the dihedral angle between the two benzene rings is 32.1 (2)°. 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, Foro et al. (2008 ); Gowda, Tokarčík et al. (2008 ).

Experimental

Crystal data

C₁₃H₈Cl₃NO
M_r = 300.55
Orthorhombic, P b c a
a = 14.699 (1) Å
b = 8.736 (1) Å
c = 20.445 (2) Å
V = 2625.4 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.68 mm⁻¹
T = 299 (2) K
0.38 × 0.14 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.781, T_max = 0.960
12954 measured reflections
2686 independent reflections
1288 reflections with I > 2σ(I)
R_int = 0.094

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.230
S = 1.08
2686 reflections
166 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.81 (5)	2.14 (5)	2.913 (5)	160 (5)
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: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018072/ci2616sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018072/ci2616Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of 2-chloro-N-(3,5-dichlorophenyl)-benzamide (N35DCP2CBA) has been determined to explore the effect of substituents on the structure of benzanilides (Gowda et al., 2003; Gowda, Foro et al., 2008; Gowda, Tokarčík et al., 2008). The N—H and C═O bonds in the amide group of N35DCP2CBA are trans to each other (Fig.1), similar to that observed in N-(3-chlorophenyl)-benzamide(N3CPBA) (Gowda, Tokarčík et al., 2008), N-(3,5-dichlorophenyl)-benzamide (N35DCPBA) (Gowda, Foro et al., 2008), 2-chloro-N-(phenyl)-benzamide (NP2CBA) (Gowda et al., 2003) and other benzanilides. Further, the conformation of the C═O bond in the structure of N35DCP2CBA is anti to the ortho-chloro substituent in the benzoyl ring, compared to the syn conformation observed in NP2CBA. The amide group –NHCO– makes dihedral angles of 63.1 (12)° and 31.1 (17)° with the benzoyl and aniline rings, respectively, while the two benzene rings (benzoyl and aniline) form a dihedral angle of 32.1 (2)°, compared to the corresponding values of 14.3 (8)°, 44.4 (4)° and 58.3 (1)° in N35DCPBA.

In the crystal structure, the molecules are linked by N—H···O hydrogen bonds (Table 1) forming chains running along the a axis, as shown in Fig. 2.

Related literature top

For related literature, see: Gowda et al. (2003); Gowda, Foro et al. (2008); Gowda, Tokarčík et al. (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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

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. Molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

2-Chloro-N-(3,5-dichlorophenyl)benzamide top

Crystal data top

C₁₃H₈Cl₃NO	F(000) = 1216
M_r = 300.55	D_x = 1.521 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2008 reflections
a = 14.699 (1) Å	θ = 2.3–28.0°
b = 8.736 (1) Å	µ = 0.68 mm⁻¹
c = 20.445 (2) Å	T = 299 K
V = 2625.4 (4) Å³	Needle, colourless
Z = 8	0.38 × 0.14 × 0.06 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	2686 independent reflections
Radiation source: fine-focus sealed tube	1288 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.094
Rotation method using ω and ϕ scans	θ_max = 26.4°, θ_min = 2.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −16→18
T_min = 0.781, T_max = 0.960	k = −10→10
12954 measured reflections	l = −25→25

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) = 0.230	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.12P)²] where P = (F_o² + 2F_c²)/3
2686 reflections	(Δ/σ)_max = 0.001
166 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₃H₈Cl₃NO	V = 2625.4 (4) Å³
M_r = 300.55	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.699 (1) Å	µ = 0.68 mm⁻¹
b = 8.736 (1) Å	T = 299 K
c = 20.445 (2) Å	0.38 × 0.14 × 0.06 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	2686 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	1288 reflections with I > 2σ(I)
T_min = 0.781, T_max = 0.960	R_int = 0.094
12954 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.230	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.45 e Å⁻³
2686 reflections	Δρ_min = −0.34 e Å⁻³
166 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
Cl1	0.60823 (8)	0.38987 (17)	0.43298 (7)	0.0724 (5)
Cl2	0.35071 (9)	0.06746 (18)	0.55821 (7)	0.0769 (5)
Cl3	0.27012 (13)	0.5045 (3)	0.22328 (10)	0.1267 (9)
O1	0.1652 (2)	0.2743 (4)	0.36978 (19)	0.0721 (11)
N1	0.2723 (2)	0.4586 (4)	0.3792 (2)	0.0479 (10)
H1N	0.284 (3)	0.545 (6)	0.367 (2)	0.057*
C1	0.3381 (3)	0.3802 (5)	0.4176 (2)	0.0444 (10)
C2	0.4295 (3)	0.4206 (5)	0.4086 (2)	0.0500 (11)
H2	0.4460	0.4947	0.3782	0.060*
C3	0.4950 (3)	0.3468 (5)	0.4463 (2)	0.0533 (12)
C4	0.4722 (3)	0.2395 (5)	0.4929 (2)	0.0551 (12)
H4	0.5165	0.1927	0.5185	0.066*
C5	0.3819 (3)	0.2042 (5)	0.5002 (2)	0.0485 (11)
C6	0.3138 (3)	0.2729 (5)	0.4639 (2)	0.0455 (10)
H6	0.2531	0.2474	0.4706	0.055*
C7	0.1939 (3)	0.4018 (5)	0.3566 (2)	0.0463 (11)
C8	0.1385 (3)	0.5072 (4)	0.3149 (2)	0.0421 (10)
C9	0.1654 (3)	0.5573 (6)	0.2540 (3)	0.0619 (13)
C10	0.1078 (5)	0.6459 (7)	0.2155 (3)	0.090 (2)
H10	0.1259	0.6788	0.1742	0.108*
C11	0.0241 (5)	0.6837 (7)	0.2398 (4)	0.094 (2)
H11	−0.0148	0.7439	0.2148	0.113*
C12	−0.0030 (4)	0.6354 (7)	0.2991 (4)	0.0825 (18)
H12	−0.0604	0.6622	0.3144	0.099*
C13	0.0520 (3)	0.5485 (5)	0.3367 (3)	0.0577 (13)
H13	0.0320	0.5158	0.3775	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0387 (7)	0.0917 (10)	0.0867 (11)	−0.0057 (6)	−0.0020 (6)	0.0066 (8)
Cl2	0.0570 (8)	0.0977 (11)	0.0759 (10)	0.0016 (7)	−0.0032 (7)	0.0413 (8)
Cl3	0.0856 (14)	0.213 (3)	0.0812 (13)	0.0195 (13)	0.0327 (10)	0.0204 (14)
O1	0.070 (2)	0.0475 (19)	0.098 (3)	−0.0128 (16)	−0.037 (2)	0.0190 (19)
N1	0.044 (2)	0.0401 (19)	0.060 (3)	−0.0031 (17)	−0.0158 (18)	0.0114 (18)
C1	0.042 (2)	0.044 (2)	0.047 (3)	0.0060 (19)	−0.0056 (19)	−0.004 (2)
C2	0.042 (3)	0.053 (3)	0.055 (3)	−0.004 (2)	0.001 (2)	−0.004 (2)
C3	0.039 (3)	0.060 (3)	0.061 (3)	−0.004 (2)	−0.008 (2)	−0.005 (3)
C4	0.046 (3)	0.068 (3)	0.052 (3)	0.010 (2)	−0.009 (2)	0.003 (3)
C5	0.044 (2)	0.052 (2)	0.050 (3)	0.002 (2)	0.000 (2)	0.008 (2)
C6	0.035 (2)	0.047 (2)	0.055 (3)	0.0028 (19)	−0.002 (2)	0.004 (2)
C7	0.043 (3)	0.041 (2)	0.055 (3)	0.0052 (19)	−0.007 (2)	−0.002 (2)
C8	0.039 (2)	0.041 (2)	0.046 (3)	−0.0013 (17)	−0.0121 (19)	−0.002 (2)
C9	0.054 (3)	0.074 (3)	0.057 (3)	−0.001 (2)	−0.005 (2)	0.009 (3)
C10	0.111 (6)	0.095 (5)	0.065 (4)	−0.004 (4)	−0.030 (4)	0.028 (4)
C11	0.099 (6)	0.061 (4)	0.121 (7)	0.012 (3)	−0.065 (5)	0.005 (4)
C12	0.062 (4)	0.083 (4)	0.103 (5)	0.026 (3)	−0.027 (4)	−0.017 (4)
C13	0.048 (3)	0.059 (3)	0.066 (3)	0.010 (2)	−0.011 (2)	−0.007 (3)

Geometric parameters (Å, º) top

Cl1—C3	1.728 (5)	C5—C6	1.383 (6)
Cl2—C5	1.744 (5)	C6—H6	0.93
Cl3—C9	1.725 (6)	C7—C8	1.496 (6)
O1—C7	1.221 (5)	C8—C9	1.376 (7)
N1—C7	1.338 (6)	C8—C13	1.396 (6)
N1—C1	1.422 (5)	C9—C10	1.392 (8)
N1—H1N	0.81 (5)	C10—C11	1.368 (9)
C1—C6	1.380 (6)	C10—H10	0.93
C1—C2	1.400 (6)	C11—C12	1.344 (9)
C2—C3	1.392 (6)	C11—H11	0.93
C2—H2	0.93	C12—C13	1.350 (7)
C3—C4	1.378 (6)	C12—H12	0.93
C4—C5	1.371 (6)	C13—H13	0.93
C4—H4	0.93

C7—N1—C1	126.7 (4)	O1—C7—N1	124.1 (4)
C7—N1—H1N	115 (3)	O1—C7—C8	119.9 (4)
C1—N1—H1N	118 (4)	N1—C7—C8	115.9 (4)
C6—C1—C2	120.7 (4)	C9—C8—C13	117.9 (4)
C6—C1—N1	122.0 (4)	C9—C8—C7	123.7 (4)
C2—C1—N1	117.3 (4)	C13—C8—C7	118.2 (4)
C3—C2—C1	118.3 (4)	C8—C9—C10	120.9 (5)
C3—C2—H2	120.9	C8—C9—Cl3	120.0 (4)
C1—C2—H2	120.9	C10—C9—Cl3	119.0 (5)
C4—C3—C2	122.0 (4)	C11—C10—C9	118.5 (6)
C4—C3—Cl1	119.4 (4)	C11—C10—H10	120.8
C2—C3—Cl1	118.5 (4)	C9—C10—H10	120.8
C5—C4—C3	117.6 (4)	C12—C11—C10	121.2 (5)
C5—C4—H4	121.2	C12—C11—H11	119.4
C3—C4—H4	121.2	C10—C11—H11	119.4
C4—C5—C6	123.0 (4)	C11—C12—C13	120.8 (6)
C4—C5—Cl2	118.8 (3)	C11—C12—H12	119.6
C6—C5—Cl2	118.1 (3)	C13—C12—H12	119.6
C1—C6—C5	118.4 (4)	C12—C13—C8	120.6 (5)
C1—C6—H6	120.8	C12—C13—H13	119.7
C5—C6—H6	120.8	C8—C13—H13	119.7

C7—N1—C1—C6	−35.1 (7)	O1—C7—C8—C9	−115.6 (6)
C7—N1—C1—C2	147.4 (5)	N1—C7—C8—C9	66.7 (6)
C6—C1—C2—C3	1.6 (6)	O1—C7—C8—C13	59.7 (6)
N1—C1—C2—C3	179.1 (4)	N1—C7—C8—C13	−118.0 (5)
C1—C2—C3—C4	−1.8 (7)	C13—C8—C9—C10	−0.2 (7)
C1—C2—C3—Cl1	177.2 (3)	C7—C8—C9—C10	175.1 (5)
C2—C3—C4—C5	1.5 (7)	C13—C8—C9—Cl3	−177.8 (4)
Cl1—C3—C4—C5	−177.5 (4)	C7—C8—C9—Cl3	−2.5 (6)
C3—C4—C5—C6	−1.1 (7)	C8—C9—C10—C11	0.7 (9)
C3—C4—C5—Cl2	179.4 (3)	Cl3—C9—C10—C11	178.3 (5)
C2—C1—C6—C5	−1.2 (6)	C9—C10—C11—C12	−0.7 (10)
N1—C1—C6—C5	−178.6 (4)	C10—C11—C12—C13	0.3 (9)
C4—C5—C6—C1	1.0 (7)	C11—C12—C13—C8	0.2 (8)
Cl2—C5—C6—C1	−179.5 (3)	C9—C8—C13—C12	−0.2 (7)
C1—N1—C7—O1	4.9 (8)	C7—C8—C13—C12	−175.8 (4)
C1—N1—C7—C8	−177.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.81 (5)	2.14 (5)	2.913 (5)	160 (5)

Symmetry code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₈Cl₃NO
M_r	300.55
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	299
a, b, c (Å)	14.699 (1), 8.736 (1), 20.445 (2)
V (Å³)	2625.4 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.68
Crystal size (mm)	0.38 × 0.14 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.781, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	12954, 2686, 1288
R_int	0.094
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.230, 1.09
No. of reflections	2686
No. of parameters	166
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.34

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.81 (5)	2.14 (5)	2.913 (5)	160 (5)

Symmetry code: (i) −x+1/2, y+1/2, z.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o1243. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230. CAS Google Scholar
Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o462. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar