4-Chloro-N-(2-chloro­phen­yl)benzamide

Saeed, A.; Khera, R.A.; Gotoh, K.; Ishida, H.

doi:10.1107/S1600536808028882

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1934

doi:10.1107/S1600536808028882

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4-Chloro-N-(2-chlorophenyl)benzamide

Aamer Saeed,^a ^* Rasheed Ahmad Khera,^a Kazuma Gotoh ^b and Hiroyuki Ishida ^b

^aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, Japan
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 19 August 2008; accepted 9 September 2008; online 13 September 2008)

In the molecular structure of the title compound, C₁₃H₉Cl₂NO, the amide N—C=O plane makes dihedral angles of 31.53 (8) and 36.23 (8)°, respectively, with the 4-chloro- and 2-chlorophenyl rings. The dihedral angle between the two benzene rings is 6.25 (8)°. The molecules are stacked in columns along the b axis through intermolecular N—H⋯O hydrogen bonds. The columns are further connected by weak C—H⋯O hydrogen bonds. The compound is not isomorphous with the fluoro analogue.

Related literature

For general background, see: Capdeville et al. (2002 ); Chopra & Row (2005 ); Ho et al. (2002 ); Igawa et al. (1999 ); Jackson et al. (1994 ); Makino et al. (2003 ); Zhichkin et al. (2007 ). For related structures, see: Chopra & Row (2005).

Experimental

Crystal data

C₁₃H₉Cl₂NO
M_r = 266.13
Monoclinic, P 2₁ /n
a = 10.7913 (14) Å
b = 4.8078 (6) Å
c = 23.570 (3) Å
β = 97.718 (3)°
V = 1211.8 (3) Å³
Z = 4
Mo- Kα radiation
μ = 0.52 mm⁻¹
T = 223 (1) K
0.35 × 0.31 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID II diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.884, T_max = 0.975
14924 measured reflections
3527 independent reflections
1847 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.154
S = 1.00
3527 reflections
158 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.85 (2)	2.12 (2)	2.901 (2)	154 (2)
C2—H2⋯O1ⁱⁱ	0.94	2.59	3.456 (3)	153
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+2, -z+1.

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028882/bh2189sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808028882/bh2189Isup2.hkl

checkCIF report

Comment top

The benzanilide core is present in compounds with a wide range of biological activities, and for this reason it has been called a privileged structure. Benzanilides serve as intermediates towards benzothiadiazin-4-ones (Makino et al., 2003), benzodiazepine-2,5-diones (Ho et al., 2002), and 2,3-disubstituted 3H-quinazoline-4-ones (Zhichkin et al., 2007). Benzanilides have established their efficacy as centroid elements of ligands that bind to a wide variety of receptor types. Thus, benzanilides containing aminoalkyl groups originally designed as peptidomimetic compounds, have been incorporated in an Arg-Gly-Asp cyclic peptide, yielding a high affinity GPIIb/IIIa ligand (Jackson et al., 1994). Imatinib is an ATP-site binding kinase inhibitor and platelet-derived growth factor receptor kinase (Capdeville et al., 2002). Benzamides have activities as acetyl-CoA carboxylase and farnesyl transferase inhibitors (Igawa et al., 1999).

In the crystal structure of the title compound (Fig. 1), the molecules are stacked in columns along the b cell-axis through intermolecular N—H···O hydrogen bonds (Table 1). The columns are also connected by weak C—H···O hydrogen bonds (Fig. 2). No significant π–π interactions are observed in the columns. The title compound is not isomorphous with the F analogue compound, 4-fluoro-N-(2-fluorophenyl)-benzamide, which exhibits a dimorphic behaviour, with non-centrosymmetric space groups P2₁ and Pca2₁ (Chopra & Row, 2005). The different crystal structures of the F analogue are probably originated from the intermolecular C—H···F interactions.

Related literature top

For related literature, see: Capdeville et al. (2002); Chopra & Row (2005); Ho et al. (2002); Igawa et al. (1999); Jackson et al. (1994); Makino et al. (2003); Zhichkin et al. (2007).

Experimental top

4-Chorobenzoyl chloride (5.4 mmol) in CHCl₃ was treated with 2-chloroaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 4 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with aq. 1 M HCl and saturated aq. NaHCO₃. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue in CHCl₃ afforded the title compound (84%). Anal. calcd. for C₁₃H₉Cl₂NO: C 58.67, H 3.41, N 5.26%; found: C 58.23, H 3.46, N 5.08%.

Computing details top

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO (Rigaku/MSC, 2004); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound. The displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. Crystal packing, viewed along the b axis. Intermolecular C—H···O hydrogen bonds are shown as dashed lines.

4-Chloro-N-(2-chlorophenyl)benzamide top

Crystal data top

C₁₃H₉Cl₂NO	F(000) = 544.00
M_r = 266.13	D_x = 1.459 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 8924 reflections
a = 10.7913 (14) Å	θ = 3.0–30.0°
b = 4.8078 (6) Å	µ = 0.52 mm⁻¹
c = 23.570 (3) Å	T = 223 K
β = 97.718 (3)°	Plate, colourless
V = 1211.8 (3) Å³	0.35 × 0.31 × 0.05 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID II diffractometer	1847 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.042
ω scans	θ_max = 30.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −15→15
T_min = 0.884, T_max = 0.975	k = −6→6
14924 measured reflections	l = −31→33
3527 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	0 constraints
R[F² > 2σ(F²)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.154	w = 1/[σ²(F_o²) + (0.079P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3527 reflections	Δρ_max = 0.23 e Å⁻³
158 parameters	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₃H₉Cl₂NO	V = 1211.8 (3) Å³
M_r = 266.13	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.7913 (14) Å	µ = 0.52 mm⁻¹
b = 4.8078 (6) Å	T = 223 K
c = 23.570 (3) Å	0.35 × 0.31 × 0.05 mm
β = 97.718 (3)°

Data collection top

Rigaku R-AXIS RAPID II diffractometer	3527 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1847 reflections with I > 2σ(I)
T_min = 0.884, T_max = 0.975	R_int = 0.042
14924 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.23 e Å⁻³
3527 reflections	Δρ_min = −0.39 e Å⁻³
158 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.01681 (5)	0.18996 (11)	0.55784 (3)	0.0701 (2)
Cl2	0.40856 (8)	0.29994 (18)	0.27592 (3)	0.1044 (3)
O1	0.31900 (14)	0.9176 (3)	0.52035 (6)	0.0704 (4)
N1	0.24949 (15)	0.4883 (3)	0.54060 (7)	0.0533 (4)
H1	0.246 (2)	0.321 (5)	0.5293 (10)	0.074 (7)*
C1	0.32607 (17)	0.5666 (4)	0.45021 (8)	0.0523 (4)
C2	0.4236 (2)	0.6900 (4)	0.42566 (10)	0.0650 (6)
H2	0.4721	0.8303	0.4456	0.078*
C3	0.4487 (2)	0.6070 (5)	0.37257 (11)	0.0725 (6)
H3	0.5152	0.6882	0.3565	0.087*
C4	0.3765 (2)	0.4053 (5)	0.34303 (10)	0.0695 (6)
C5	0.2787 (2)	0.2815 (5)	0.36606 (10)	0.0680 (6)
H5	0.2295	0.1444	0.3454	0.082*
C6	0.25440 (19)	0.3623 (4)	0.41982 (9)	0.0599 (5)
H6	0.1887	0.2780	0.4359	0.072*
C7	0.29897 (17)	0.6734 (3)	0.50645 (9)	0.0528 (5)
C8	0.20311 (18)	0.5546 (4)	0.59237 (8)	0.0531 (4)
C9	0.09424 (19)	0.4263 (4)	0.60525 (8)	0.0554 (5)
C10	0.0457 (2)	0.4875 (5)	0.65537 (9)	0.0727 (6)
H10	−0.0267	0.3965	0.6639	0.087*
C11	0.1041 (3)	0.6823 (6)	0.69252 (11)	0.0870 (8)
H11	0.0701	0.7295	0.7259	0.104*
C12	0.2115 (3)	0.8069 (5)	0.68088 (11)	0.0833 (8)
H12	0.2517	0.9368	0.7069	0.100*
C13	0.2623 (2)	0.7451 (4)	0.63118 (10)	0.0694 (6)
H13	0.3366	0.8322	0.6239	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0638 (4)	0.0686 (4)	0.0792 (4)	−0.0099 (2)	0.0140 (3)	−0.0038 (3)
Cl2	0.1190 (6)	0.1252 (6)	0.0763 (5)	0.0111 (5)	0.0399 (4)	−0.0089 (4)
O1	0.0844 (10)	0.0411 (7)	0.0895 (11)	−0.0058 (7)	0.0258 (8)	−0.0078 (7)
N1	0.0588 (10)	0.0416 (8)	0.0610 (10)	−0.0015 (7)	0.0138 (7)	−0.0073 (7)
C1	0.0492 (11)	0.0427 (9)	0.0664 (12)	0.0048 (8)	0.0125 (9)	0.0010 (8)
C2	0.0556 (12)	0.0544 (11)	0.0883 (16)	−0.0030 (9)	0.0215 (11)	−0.0019 (10)
C3	0.0654 (14)	0.0695 (13)	0.0890 (16)	0.0007 (11)	0.0333 (12)	0.0051 (12)
C4	0.0710 (14)	0.0737 (14)	0.0667 (13)	0.0155 (11)	0.0193 (11)	0.0037 (11)
C5	0.0673 (14)	0.0718 (13)	0.0649 (14)	−0.0011 (11)	0.0085 (10)	−0.0083 (10)
C6	0.0560 (12)	0.0605 (11)	0.0647 (12)	−0.0051 (9)	0.0137 (9)	−0.0010 (9)
C7	0.0468 (10)	0.0411 (9)	0.0714 (12)	0.0028 (7)	0.0114 (9)	−0.0016 (8)
C8	0.0581 (11)	0.0459 (9)	0.0546 (11)	0.0081 (8)	0.0050 (8)	−0.0026 (8)
C9	0.0584 (12)	0.0542 (10)	0.0536 (10)	0.0086 (9)	0.0078 (9)	0.0019 (9)
C10	0.0785 (15)	0.0826 (14)	0.0596 (12)	0.0170 (12)	0.0185 (11)	0.0073 (12)
C11	0.111 (2)	0.0959 (19)	0.0554 (14)	0.0370 (17)	0.0142 (14)	−0.0010 (13)
C12	0.105 (2)	0.0804 (16)	0.0593 (14)	0.0151 (15)	−0.0073 (13)	−0.0202 (11)
C13	0.0756 (15)	0.0632 (12)	0.0665 (14)	0.0028 (11)	−0.0010 (11)	−0.0106 (10)

Geometric parameters (Å, º) top

Cl1—C9	1.729 (2)	C5—C6	1.384 (3)
Cl2—C4	1.739 (2)	C5—H5	0.9400
O1—C7	1.230 (2)	C6—H6	0.9400
N1—C7	1.357 (2)	C8—C13	1.388 (3)
N1—C8	1.416 (2)	C8—C9	1.396 (3)
N1—H1	0.84 (2)	C9—C10	1.387 (3)
C1—C6	1.388 (3)	C10—C11	1.376 (4)
C1—C2	1.399 (3)	C10—H10	0.9400
C1—C7	1.487 (3)	C11—C12	1.364 (4)
C2—C3	1.375 (3)	C11—H11	0.9400
C2—H2	0.9400	C12—C13	1.391 (3)
C3—C4	1.373 (3)	C12—H12	0.9400
C3—H3	0.9400	C13—H13	0.9400
C4—C5	1.384 (3)

C7—N1—C8	125.20 (16)	O1—C7—N1	122.49 (18)
C7—N1—H1	116.3 (16)	O1—C7—C1	121.24 (16)
C8—N1—H1	118.4 (16)	N1—C7—C1	116.26 (16)
C6—C1—C2	118.98 (18)	C13—C8—C9	118.34 (19)
C6—C1—C7	122.80 (16)	C13—C8—N1	122.11 (19)
C2—C1—C7	118.10 (18)	C9—C8—N1	119.55 (17)
C3—C2—C1	120.3 (2)	C10—C9—C8	121.1 (2)
C3—C2—H2	119.8	C10—C9—Cl1	119.00 (17)
C1—C2—H2	119.8	C8—C9—Cl1	119.86 (15)
C4—C3—C2	119.9 (2)	C11—C10—C9	119.5 (2)
C4—C3—H3	120.0	C11—C10—H10	120.2
C2—C3—H3	120.0	C9—C10—H10	120.2
C3—C4—C5	121.0 (2)	C12—C11—C10	120.0 (2)
C3—C4—Cl2	119.89 (18)	C12—C11—H11	120.0
C5—C4—Cl2	119.1 (2)	C10—C11—H11	120.0
C6—C5—C4	119.1 (2)	C11—C12—C13	121.2 (2)
C6—C5—H5	120.4	C11—C12—H12	119.4
C4—C5—H5	120.4	C13—C12—H12	119.4
C5—C6—C1	120.66 (19)	C8—C13—C12	119.8 (2)
C5—C6—H6	119.7	C8—C13—H13	120.1
C1—C6—H6	119.7	C12—C13—H13	120.1

C6—C1—C2—C3	−0.8 (3)	C2—C1—C7—N1	−151.15 (18)
C7—C1—C2—C3	−177.11 (19)	C7—N1—C8—C13	−39.9 (3)
C1—C2—C3—C4	1.1 (3)	C7—N1—C8—C9	140.0 (2)
C2—C3—C4—C5	−0.5 (3)	C13—C8—C9—C10	0.3 (3)
C2—C3—C4—Cl2	−179.88 (18)	N1—C8—C9—C10	−179.58 (17)
C3—C4—C5—C6	−0.4 (3)	C13—C8—C9—Cl1	179.47 (15)
Cl2—C4—C5—C6	179.04 (17)	N1—C8—C9—Cl1	−0.4 (2)
C4—C5—C6—C1	0.6 (3)	C8—C9—C10—C11	1.4 (3)
C2—C1—C6—C5	0.0 (3)	Cl1—C9—C10—C11	−177.82 (17)
C7—C1—C6—C5	176.07 (19)	C9—C10—C11—C12	−2.2 (4)
C8—N1—C7—O1	7.0 (3)	C10—C11—C12—C13	1.4 (4)
C8—N1—C7—C1	−171.95 (16)	C9—C8—C13—C12	−1.1 (3)
C6—C1—C7—O1	−146.2 (2)	N1—C8—C13—C12	178.72 (19)
C2—C1—C7—O1	29.9 (3)	C11—C12—C13—C8	0.3 (4)
C6—C1—C7—N1	32.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.85 (2)	2.12 (2)	2.901 (2)	154 (2)
C2—H2···O1ⁱⁱ	0.94	2.59	3.456 (3)	153
C13—H13···O1	0.94	2.46	2.884 (3)	108

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₉Cl₂NO
M_r	266.13
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	223
a, b, c (Å)	10.7913 (14), 4.8078 (6), 23.570 (3)
β (°)	97.718 (3)
V (Å³)	1211.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.35 × 0.31 × 0.05

Data collection
Diffractometer	Rigaku R-AXIS RAPID II diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.884, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	14924, 3527, 1847
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.154, 1.00
No. of reflections	3527
No. of parameters	158
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.39

Computer programs: PROCESS-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.85 (2)	2.12 (2)	2.901 (2)	154 (2)
C2—H2···O1ⁱⁱ	0.94	2.59	3.456 (3)	153

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+2, −z+1.

Acknowledgements

AS gratefully acknowledges a research grant from Quaid-I-Azam University, Islamabad.

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