2,6-Dichloro-N-(4-chloro­phen­yl)benzamide

Zhu, J.; Li, M.; Wei, H.; Wang, J.; Guo, C.

doi:10.1107/S1600536812007556

organic compounds

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Volume 68| Part 3| March 2012| Page o843

doi:10.1107/S1600536812007556

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2,6-Dichloro-N-(4-chlorophenyl)benzamide

Jing Zhu,^a Ming Li,^a Hong-xia Wei,^a Jian-qiang Wang ^a and Cheng Guo ^a ^*

^aCollege of Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: guocheng@njut.edu.cn

(Received 18 February 2012; accepted 20 February 2012; online 24 February 2012)

In the title compound, C₁₃H₈Cl₃NO, the dihedral angle between the benzene rings is 63.2 (2)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into C(4) chains propagating in [001]. Weak aromatic π–π stacking also occurs [centroid–centroid separations = 3.759 (3) and 3.776 (3) Å].

Related literature

For further synthetic details, see: Lai & Huang (2005 ).

Experimental

Crystal data

C₁₃H₈Cl₃NO
M_r = 300.55
Monoclinic, P 2₁ /c
a = 11.241 (2) Å
b = 12.590 (3) Å
c = 9.6450 (19) Å
β = 100.60 (3)°
V = 1341.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.67 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.825, T_max = 0.936
2587 measured reflections
2459 independent reflections
1481 reflections with I > 2σ(I)
R_int = 0.031
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.181
S = 1.00
2459 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯Oⁱ	0.86	1.97	2.828 (4)	176
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97; software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812007556/hb6644sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007556/hb6644Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007556/hb6644Isup3.cml

checkCIF report

Related literature top

For further synthetic details, see: Lai et al. (2005).

Experimental top

2,6-Dichlorobenzoyl chloride (0.02 mol, 4.20 g)and 4-chloroaniline (0.02 mol, 2.55 g) were refluxed in triethylamine (6 ml) and tetrahydrofuran (50 ml) for 8h, then the solvents were evaporated to give raw product, which was finally washed by water and collected by filtration. Colourless blocks were obtained by slow evaporation of an ethyl acetate solution.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I) viewed down the b axis. Hydrogen bonds are drawn as dashed lines.

2,6-Dichloro-N-(4-chlorophenyl)benzamide top

Crystal data top

C₁₃H₈Cl₃NO	D_x = 1.488 Mg m⁻³
M_r = 300.55	Melting point: 397 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.241 (2) Å	Cell parameters from 25 reflections
b = 12.590 (3) Å	θ = 9–13°
c = 9.6450 (19) Å	µ = 0.67 mm⁻¹
β = 100.60 (3)°	T = 293 K
V = 1341.7 (5) Å³	Block, colourless
Z = 4	0.30 × 0.20 × 0.10 mm
F(000) = 608

Data collection top

Enraf–Nonius CAD-4 diffractometer	1481 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 25.4°, θ_min = 1.8°
ω/2θ scans	h = −13→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→15
T_min = 0.825, T_max = 0.936	l = −11→11
2587 measured reflections	3 standard reflections every 200 reflections
2459 independent reflections	intensity decay: 1%

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.181	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.095P)²] where P = (F_o² + 2F_c²)/3
2459 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₃H₈Cl₃NO	V = 1341.7 (5) Å³
M_r = 300.55	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.241 (2) Å	µ = 0.67 mm⁻¹
b = 12.590 (3) Å	T = 293 K
c = 9.6450 (19) Å	0.30 × 0.20 × 0.10 mm
β = 100.60 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1481 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.031
T_min = 0.825, T_max = 0.936	3 standard reflections every 200 reflections
2587 measured reflections	intensity decay: 1%
2459 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.181	H-atom parameters constrained
S = 1.00	Δρ_max = 0.26 e Å⁻³
2459 reflections	Δρ_min = −0.29 e Å⁻³
163 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N	0.7580 (3)	0.3117 (2)	0.1127 (3)	0.0423 (8)
H0A	0.7677	0.2870	0.1972	0.051*
O	0.7776 (3)	0.2668 (2)	−0.1093 (3)	0.0660 (9)
Cl1	0.57123 (16)	0.75067 (10)	0.0703 (2)	0.1055 (6)
C1	0.7243 (4)	0.4801 (4)	−0.0171 (5)	0.0593 (12)
H1A	0.7651	0.4547	−0.0859	0.071*
Cl2	0.64198 (10)	0.05573 (10)	0.07481 (12)	0.0617 (4)
C2	0.6810 (5)	0.5830 (4)	−0.0246 (5)	0.0668 (13)
H2A	0.6917	0.6268	−0.0990	0.080*
Cl3	1.06285 (13)	0.25773 (11)	0.06642 (19)	0.0927 (6)
C3	0.6224 (4)	0.6202 (4)	0.0774 (6)	0.0594 (12)
C4	0.6040 (4)	0.5568 (4)	0.1854 (6)	0.0660 (13)
H4A	0.5638	0.5829	0.2543	0.079*
C5	0.6460 (4)	0.4524 (4)	0.1924 (5)	0.0544 (11)
H5A	0.6323	0.4082	0.2652	0.065*
C6	0.7070 (3)	0.4148 (3)	0.0926 (4)	0.0394 (9)
C7	0.7928 (4)	0.2481 (3)	0.0165 (4)	0.0443 (10)
C8	0.8579 (4)	0.1497 (3)	0.0788 (4)	0.0434 (10)
C9	0.7988 (4)	0.0590 (3)	0.1085 (4)	0.0465 (10)
C10	0.8603 (5)	−0.0302 (4)	0.1654 (5)	0.0595 (12)
H10A	0.8188	−0.0911	0.1831	0.071*
C11	0.9838 (5)	−0.0267 (5)	0.1951 (6)	0.0765 (15)
H11A	1.0264	−0.0859	0.2346	0.092*
C12	1.0461 (5)	0.0615 (5)	0.1683 (6)	0.0753 (15)
H12A	1.1302	0.0628	0.1906	0.090*
C13	0.9836 (4)	0.1479 (4)	0.1082 (5)	0.0593 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.055 (2)	0.0430 (19)	0.0289 (16)	0.0040 (16)	0.0070 (14)	0.0032 (15)
O	0.109 (3)	0.0540 (19)	0.0365 (17)	0.0039 (17)	0.0164 (17)	−0.0042 (14)
Cl1	0.1079 (13)	0.0498 (8)	0.1576 (16)	0.0283 (8)	0.0215 (11)	0.0106 (9)
C1	0.077 (3)	0.052 (3)	0.051 (3)	0.006 (2)	0.018 (2)	0.010 (2)
Cl2	0.0515 (7)	0.0637 (7)	0.0707 (8)	−0.0022 (5)	0.0132 (5)	0.0087 (6)
C2	0.085 (4)	0.046 (3)	0.068 (3)	0.004 (3)	0.011 (3)	0.016 (2)
Cl3	0.0706 (9)	0.0743 (10)	0.1392 (14)	−0.0252 (7)	0.0347 (9)	−0.0239 (9)
C3	0.048 (3)	0.043 (3)	0.084 (4)	0.003 (2)	0.002 (2)	0.003 (2)
C4	0.063 (3)	0.063 (3)	0.078 (3)	0.013 (2)	0.028 (3)	−0.007 (3)
C5	0.062 (3)	0.052 (3)	0.053 (3)	0.004 (2)	0.019 (2)	0.006 (2)
C6	0.042 (2)	0.036 (2)	0.039 (2)	−0.0007 (17)	0.0032 (17)	−0.0009 (17)
C7	0.058 (3)	0.044 (2)	0.031 (2)	−0.0057 (19)	0.0088 (18)	−0.0004 (18)
C8	0.052 (2)	0.043 (2)	0.036 (2)	0.0019 (19)	0.0082 (18)	−0.0073 (18)
C9	0.049 (2)	0.052 (2)	0.040 (2)	0.006 (2)	0.0127 (18)	−0.001 (2)
C10	0.071 (3)	0.049 (3)	0.061 (3)	0.013 (2)	0.021 (2)	0.011 (2)
C11	0.076 (4)	0.076 (4)	0.076 (4)	0.032 (3)	0.008 (3)	0.011 (3)
C12	0.046 (3)	0.095 (4)	0.082 (4)	0.013 (3)	0.003 (3)	−0.013 (3)
C13	0.055 (3)	0.052 (3)	0.071 (3)	−0.003 (2)	0.013 (2)	−0.015 (2)

Geometric parameters (Å, º) top

N—C7	1.338 (5)	C4—H4A	0.9300
N—C6	1.417 (5)	C5—C6	1.366 (5)
N—H0A	0.8600	C5—H5A	0.9300
O—C7	1.216 (4)	C7—C8	1.506 (5)
Cl1—C3	1.737 (5)	C8—C9	1.378 (6)
C1—C6	1.381 (5)	C8—C13	1.389 (6)
C1—C2	1.382 (6)	C9—C10	1.379 (6)
C1—H1A	0.9300	C10—C11	1.365 (7)
Cl2—C9	1.733 (4)	C10—H10A	0.9300
C2—C3	1.365 (7)	C11—C12	1.363 (7)
C2—H2A	0.9300	C11—H11A	0.9300
Cl3—C13	1.732 (5)	C12—C13	1.365 (7)
C3—C4	1.358 (7)	C12—H12A	0.9300
C4—C5	1.394 (6)

C7—N—C6	128.0 (3)	O—C7—N	124.9 (4)
C7—N—H0A	116.0	O—C7—C8	121.7 (4)
C6—N—H0A	116.0	N—C7—C8	113.4 (3)
C6—C1—C2	120.1 (4)	C9—C8—C13	117.1 (4)
C6—C1—H1A	120.0	C9—C8—C7	123.2 (4)
C2—C1—H1A	120.0	C13—C8—C7	119.7 (4)
C3—C2—C1	119.8 (4)	C8—C9—C10	122.2 (4)
C3—C2—H2A	120.1	C8—C9—Cl2	119.6 (3)
C1—C2—H2A	120.1	C10—C9—Cl2	118.3 (3)
C4—C3—C2	120.9 (4)	C11—C10—C9	118.2 (5)
C4—C3—Cl1	119.4 (4)	C11—C10—H10A	120.9
C2—C3—Cl1	119.7 (4)	C9—C10—H10A	120.9
C3—C4—C5	119.6 (4)	C12—C11—C10	121.7 (5)
C3—C4—H4A	120.2	C12—C11—H11A	119.2
C5—C4—H4A	120.2	C10—C11—H11A	119.2
C6—C5—C4	120.2 (4)	C11—C12—C13	119.1 (5)
C6—C5—H5A	119.9	C11—C12—H12A	120.4
C4—C5—H5A	119.9	C13—C12—H12A	120.4
C5—C6—C1	119.5 (4)	C12—C13—C8	121.7 (5)
C5—C6—N	117.6 (3)	C12—C13—Cl3	119.2 (4)
C1—C6—N	122.7 (4)	C8—C13—Cl3	119.1 (4)

C6—C1—C2—C3	0.8 (7)	O—C7—C8—C13	82.0 (5)
C1—C2—C3—C4	−1.2 (8)	N—C7—C8—C13	−96.3 (5)
C1—C2—C3—Cl1	178.4 (4)	C13—C8—C9—C10	0.3 (6)
C2—C3—C4—C5	0.2 (7)	C7—C8—C9—C10	179.9 (4)
Cl1—C3—C4—C5	−179.4 (4)	C13—C8—C9—Cl2	179.9 (3)
C3—C4—C5—C6	1.2 (7)	C7—C8—C9—Cl2	−0.5 (5)
C4—C5—C6—C1	−1.6 (6)	C8—C9—C10—C11	1.2 (6)
C4—C5—C6—N	173.8 (4)	Cl2—C9—C10—C11	−178.5 (4)
C2—C1—C6—C5	0.6 (7)	C9—C10—C11—C12	−0.8 (8)
C2—C1—C6—N	−174.5 (4)	C10—C11—C12—C13	−1.1 (8)
C7—N—C6—C5	161.0 (4)	C11—C12—C13—C8	2.6 (8)
C7—N—C6—C1	−23.7 (6)	C11—C12—C13—Cl3	−177.0 (4)
C6—N—C7—O	−5.6 (7)	C9—C8—C13—C12	−2.2 (6)
C6—N—C7—C8	172.6 (3)	C7—C8—C13—C12	178.2 (4)
O—C7—C8—C9	−97.7 (5)	C9—C8—C13—Cl3	177.4 (3)
N—C7—C8—C9	84.1 (5)	C7—C8—C13—Cl3	−2.2 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···Oⁱ	0.86	1.97	2.828 (4)	176

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₈Cl₃NO
M_r	300.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.241 (2), 12.590 (3), 9.6450 (19)
β (°)	100.60 (3)
V (Å³)	1341.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.67
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.825, 0.936
No. of measured, independent and observed [I > 2σ(I)] reflections	2587, 2459, 1481
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.181, 1.00
No. of reflections	2459
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.29

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···Oⁱ	0.86	1.97	2.828 (4)	176

Symmetry code: (i) x, −y+1/2, z+1/2.

References

Enraf–Nonius (1989). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Lai, Y.-Y. & Huang, L.-J. (2005). Bioorg. Med. Chem. 13, 265–275. Web of Science CrossRef PubMed CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o843

doi:10.1107/S1600536812007556

Open

access