2-Chloro-N-(2,6-dichloro-phen-yl)benzamide.

In the structure of the title compound (N26DCP2CBA), C(13)H(8)Cl(3)NO, the conformations of N-H and C=O bonds in the amide group are trans to each other, similar to that observed in N-(2,6-dichloro-phen-yl)benzamide, 2-chloro-N-phenyl-benzamide, 2-chloro-N-(2-chloro-phen-yl)benzamide and 2-chloro-N-(2,3-dichloro-phen-yl)benzamide with similar bond parameters. Furthermore, the position of the amide O atom is syn to the ortho-chloro group in the benzoyl ring. The amide group makes a dihedral angle of 59.8 (1)° with the benzoyl ring, while the benzoyl and aniline rings make a dihedral angle of 8.1 (2)°. The mol-ecules are linked by N-H⋯O hydrogen bonds into infinite chains running along the b axis.

Related literature

For related literature, see Gowda et al. (2003 ▶, 2007 ▶, 2008a ▶,b ▶).

Experimental

Crystal data

C13H8Cl3NO

M = 300.55

Orthorhombic,

a = 21.3949 (4) Å

b = 4.8159 (1) Å

c = 12.5036 (3) Å

V = 1288.32 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.70 mm−1

T = 295 (2) K

0.42 × 0.16 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur System diffractometer

Absorption correction: analytical [CrysAlis RED; Oxford Diffraction, 2007 ▶ (based on Clark & Reid, 1995 ▶)] T min = 0.802, T max = 0.951

26609 measured reflections

1306 independent reflections

1216 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.073

S = 1.08

1306 reflections

163 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1167 Friedel pairs

Flack parameter: 0.14 (8)

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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021223/bx2156sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021223/bx2156Isup2.hkl

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

C13H8Cl3NO	F000 = 608
Mr = 300.55	Dx = 1.55 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 13276 reflections
a = 21.3949 (4) Å	θ = 3.3–29.5º
b = 4.81590 (10) Å	µ = 0.70 mm−1
c = 12.5036 (3) Å	T = 295 (2) K
V = 1288.32 (5) Å3	Rod, colourless
Z = 4	0.42 × 0.16 × 0.08 mm

Oxford Diffraction Xcalibur System diffractometer	1306 independent reflections
Monochromator: graphite	1216 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.030
T = 295(2) K	θmax = 26.0º
ω scans with κ offsets	θmin = 5.3º
Absorption correction: analytical(CrysAlis RED; Oxford Diffraction, 2007)	h = −26→26
Tmin = 0.802, Tmax = 0.951	k = −5→5
26609 measured reflections	l = −15→15

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.027	w = 1/[σ2(Fo2) + (0.044P)2 + 0.2234P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.073	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.21 e Å−3
1306 reflections	Δρmin = −0.21 e Å−3
163 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 1167 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.14 (8)
Secondary atom site location: difference Fourier map

Experimental. CrysAlis RED, Oxford Diffraction (2007). Analytical absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995).

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
C1	0.36930 (11)	0.1547 (5)	0.4253 (2)	0.0334 (5)
C2	0.42847 (11)	0.2602 (5)	0.4746 (2)	0.0357 (6)
C3	0.48616 (13)	0.1593 (6)	0.4430 (3)	0.0429 (7)
C4	0.54063 (13)	0.2457 (7)	0.4927 (3)	0.0579 (9)
H4	0.5791	0.1756	0.4709	0.069*
C5	0.53744 (18)	0.4341 (8)	0.5737 (4)	0.0687 (12)
H5	0.5739	0.4915	0.6075	0.082*
C6	0.48090 (19)	0.5403 (8)	0.6060 (3)	0.0634 (11)
H6	0.4792	0.6695	0.6612	0.076*
C7	0.42636 (16)	0.4543 (6)	0.5560 (3)	0.0481 (8)
H7	0.3881	0.5275	0.5775	0.058*
C8	0.27485 (10)	0.2660 (5)	0.3315 (2)	0.0334 (5)
C9	0.27249 (14)	0.1003 (6)	0.2411 (3)	0.0470 (7)
C10	0.21674 (15)	0.0145 (9)	0.1969 (3)	0.0609 (10)
H10	0.2164	−0.0982	0.1365	0.073*
C11	0.16185 (15)	0.0976 (7)	0.2434 (3)	0.0592 (9)
H11	0.124	0.0388	0.2144	0.071*
C12	0.16174 (12)	0.2649 (7)	0.3313 (3)	0.0491 (7)
H12	0.1242	0.322	0.3618	0.059*
C13	0.21824 (12)	0.3488 (6)	0.3745 (3)	0.0389 (6)
N1	0.33226 (9)	0.3444 (4)	0.37870 (19)	0.0337 (5)
H1N	0.3436	0.5157	0.3775	0.04*
O1	0.35555 (10)	−0.0906 (4)	0.4302 (2)	0.0510 (6)
Cl1	0.49200 (4)	−0.07634 (17)	0.33767 (8)	0.0588 (2)
Cl2	0.34152 (4)	0.0008 (2)	0.17928 (9)	0.0734 (3)
Cl3	0.21723 (4)	0.5602 (2)	0.48512 (8)	0.0670 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0284 (12)	0.0289 (12)	0.0429 (14)	0.0002 (10)	0.0006 (11)	0.0002 (11)
C2	0.0316 (12)	0.0281 (12)	0.0473 (15)	−0.0025 (10)	−0.0049 (12)	0.0079 (11)
C3	0.0363 (14)	0.0375 (15)	0.0547 (18)	−0.0027 (11)	−0.0038 (13)	0.0107 (13)
C4	0.0299 (14)	0.0577 (19)	0.086 (2)	−0.0036 (13)	−0.0126 (16)	0.018 (2)
C5	0.051 (2)	0.060 (2)	0.095 (3)	−0.0124 (17)	−0.039 (2)	0.010 (2)
C6	0.073 (2)	0.051 (2)	0.067 (3)	−0.0040 (18)	−0.032 (2)	−0.0082 (17)
C7	0.0501 (18)	0.0384 (15)	0.0558 (19)	0.0023 (13)	−0.0142 (15)	−0.0031 (14)
C8	0.0289 (11)	0.0280 (11)	0.0435 (14)	−0.0012 (9)	−0.0038 (11)	−0.0033 (12)
C9	0.0329 (14)	0.0548 (17)	0.0532 (18)	0.0029 (12)	−0.0013 (12)	−0.0146 (15)
C10	0.0459 (18)	0.073 (2)	0.064 (2)	−0.0028 (15)	−0.0125 (17)	−0.0282 (19)
C11	0.0336 (16)	0.067 (2)	0.077 (2)	−0.0063 (14)	−0.0159 (15)	−0.0159 (19)
C12	0.0267 (12)	0.0532 (17)	0.068 (2)	0.0012 (12)	−0.0004 (14)	−0.0072 (18)
C13	0.0347 (13)	0.0348 (14)	0.0471 (16)	−0.0002 (10)	−0.0009 (11)	−0.0076 (12)
N1	0.0284 (10)	0.0227 (9)	0.0498 (13)	−0.0009 (8)	−0.0055 (9)	−0.0042 (9)
O1	0.0432 (11)	0.0228 (9)	0.0870 (17)	−0.0051 (8)	−0.0100 (11)	0.0027 (10)
Cl1	0.0449 (4)	0.0632 (5)	0.0683 (5)	0.0093 (3)	0.0088 (4)	−0.0048 (4)
Cl2	0.0437 (4)	0.1065 (7)	0.0700 (6)	0.0068 (4)	0.0051 (4)	−0.0439 (5)
Cl3	0.0447 (4)	0.0801 (6)	0.0762 (6)	0.0001 (4)	0.0058 (4)	−0.0413 (5)

C1—O1	1.219 (3)	C8—C13	1.384 (4)
C1—N1	1.343 (3)	C8—C9	1.385 (4)
C1—C2	1.497 (3)	C8—N1	1.414 (3)
C2—C7	1.383 (4)	C9—C10	1.378 (4)
C2—C3	1.384 (4)	C9—Cl2	1.734 (3)
C3—C4	1.385 (4)	C10—C11	1.370 (5)
C3—Cl1	1.743 (4)	C10—H10	0.93
C4—C5	1.361 (6)	C11—C12	1.363 (5)
C4—H4	0.93	C11—H11	0.93
C5—C6	1.374 (6)	C12—C13	1.384 (4)
C5—H5	0.93	C12—H12	0.93
C6—C7	1.387 (5)	C13—Cl3	1.717 (3)
C6—H6	0.93	N1—H1N	0.86
C7—H7	0.93
O1—C1—N1	122.6 (2)	C13—C8—C9	116.8 (2)
O1—C1—C2	120.9 (2)	C13—C8—N1	121.4 (3)
N1—C1—C2	116.5 (2)	C9—C8—N1	121.7 (2)
C7—C2—C3	118.5 (3)	C10—C9—C8	122.1 (3)
C7—C2—C1	120.3 (3)	C10—C9—Cl2	118.4 (3)
C3—C2—C1	121.1 (3)	C8—C9—Cl2	119.5 (2)
C2—C3—C4	121.1 (3)	C11—C10—C9	119.0 (3)
C2—C3—Cl1	120.6 (2)	C11—C10—H10	120.5
C4—C3—Cl1	118.3 (3)	C9—C10—H10	120.5
C5—C4—C3	119.5 (3)	C12—C11—C10	121.1 (3)
C5—C4—H4	120.3	C12—C11—H11	119.5
C3—C4—H4	120.3	C10—C11—H11	119.5
C4—C5—C6	120.7 (3)	C11—C12—C13	119.1 (3)
C4—C5—H5	119.6	C11—C12—H12	120.5
C6—C5—H5	119.6	C13—C12—H12	120.5
C5—C6—C7	119.8 (3)	C8—C13—C12	121.9 (3)
C5—C6—H6	120.1	C8—C13—Cl3	119.6 (2)
C7—C6—H6	120.1	C12—C13—Cl3	118.5 (2)
C2—C7—C6	120.4 (3)	C1—N1—C8	120.8 (2)
C2—C7—H7	119.8	C1—N1—H1N	119.6
C6—C7—H7	119.8	C8—N1—H1N	119.6
O1—C1—C2—C7	−118.3 (3)	C13—C8—C9—Cl2	177.2 (2)
N1—C1—C2—C7	60.1 (3)	N1—C8—C9—Cl2	−3.5 (4)
O1—C1—C2—C3	59.2 (4)	C8—C9—C10—C11	0.6 (6)
N1—C1—C2—C3	−122.4 (3)	Cl2—C9—C10—C11	−178.3 (3)
C7—C2—C3—C4	1.2 (4)	C9—C10—C11—C12	0.7 (7)
C1—C2—C3—C4	−176.4 (3)	C10—C11—C12—C13	−0.7 (6)
C7—C2—C3—Cl1	−177.7 (2)	C9—C8—C13—C12	1.7 (5)
C1—C2—C3—Cl1	4.7 (4)	N1—C8—C13—C12	−177.6 (3)
C2—C3—C4—C5	−0.3 (5)	C9—C8—C13—Cl3	−178.7 (2)
Cl1—C3—C4—C5	178.6 (3)	N1—C8—C13—Cl3	2.0 (4)
C3—C4—C5—C6	−0.4 (6)	C11—C12—C13—C8	−0.5 (5)
C4—C5—C6—C7	0.3 (6)	C11—C12—C13—Cl3	179.9 (3)
C3—C2—C7—C6	−1.3 (4)	O1—C1—N1—C8	−0.5 (4)
C1—C2—C7—C6	176.2 (3)	C2—C1—N1—C8	−178.9 (3)
C5—C6—C7—C2	0.6 (5)	C13—C8—N1—C1	112.2 (3)
C13—C8—C9—C10	−1.7 (5)	C9—C8—N1—C1	−67.0 (4)
N1—C8—C9—C10	177.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.02	2.840 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.02	2.840 (3)	158

Symmetry code: (i) .