2,6-Dichloro-N-(4-chloro-phen-yl)benzamide.

In the title compound, C(13)H(8)Cl(3)NO, the dihedral angle between the benzene rings is 63.2 (2)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules 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 = 300.55

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.181

S = 1.00

2459 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.29 e Å−3

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 class="Chemical">N (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812007556/hb6644sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812007556/hb6644Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H8Cl3NO	Dx = 1.488 Mg m−3
Mr = 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

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

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(Fo2) + (0.095P)2] where P = (Fo2 + 2Fc2)/3
2459 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .