2-Chloro-N-(3,5-dichloro-phenyl)-benzamide.

The amide group in the structure of the title compound (N35DCP2CBA), C(13)H(8)Cl(3)NO, is trans-planar, similar to that observed in N-(3-chloro-phen-yl)benzamide, N-(3,5-dichloro-phen-yl)benzamide, 2-chloro-N-phenyl-benzamide 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 mol-ecules 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 = 300.55

Orthorhombic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.230

S = 1.08

2686 reflections

166 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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.

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

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

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

C13H8Cl3NO	F000 = 1216
Mr = 300.55	Dx = 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 = 2.3–28.0º
b = 8.736 (1) Å	µ = 0.68 mm−1
c = 20.445 (2) Å	T = 299 (2) K
V = 2625.4 (4) Å3	Needle, colourless
Z = 8	0.38 × 0.14 × 0.06 mm

Oxford Diffraction Xcalibur diffractometer	2686 independent reflections
Radiation source: fine-focus sealed tube	1288 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.094
T = 299(2) K	θmax = 26.4º
Rotation method using ω and φ scans	θmin = 2.4º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −16→18
Tmin = 0.781, Tmax = 0.960	k = −10→10
12954 measured reflections	l = −25→25

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.230	w = 1/[σ2(Fo2) + (0.12P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
2686 reflections	Δρmax = 0.45 e Å−3
166 parameters	Δρmin = −0.34 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) .