3-Chloro-N-(3-chloro-phen-yl)benzamide.

In the crystal structure of the title compound, C(13)H(9)Cl(2)NO, the N-H and C=O bonds are anti to each other in the two independent mol-ecules. In one mol-ecule, the N-H bond is syn to the meta-chloro group of the attached ring; it is anti in the other mol-ecule. This relationship is also observed between the C=O bond and the meta-chloro substituent of its attached ring. The amide -NHCO- group makes dihedral angles of 31.5 (4) and 34.7 (3)° with the aniline rings; it makes dihedral angles of 37.4 (3) and 37.2 (3)° with the benzoyl rings. The two rings are nearly coplanar, with dihedral angles of 9.1 (2) and 7.3 (3)° in the two independent mol-ecules. Adjacent mol-ecules are linked into infinite chains through N-H⋯O hydrogen bonds.

Related literature

For background literature, see: Gowda et al. (2003 ▶, 2007 ▶, 2008 ▶).

Experimental

Crystal data

C13H9Cl2NO

M = 266.11

Monoclinic,

a = 8.577 (1) Å

b = 13.551 (1) Å

c = 10.357 (1) Å

β = 93.04 (1)°

V = 1202.1 (2) Å3

Z = 4

Cu Kα radiation

μ = 4.70 mm−1

T = 296 (2) K

0.60 × 0.28 × 0.23 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.265, T max = 0.341

3088 measured reflections

2249 independent reflections

2165 reflections with I > 2˘I)

R int = 0.022

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.131

S = 1.10

2249 reflections

308 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.49 e Å−3

Absolute structure: Flack (1983 ▶), no Friedel pairs

Flack parameter: 0.07 (2)

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); 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/S1600536808012099/ng2449sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012099/ng2449Isup2.hkl

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

C13H9Cl2NO	F000 = 544
Mr = 266.11	Dx = 1.470 Mg m−3
Monoclinic, P21	Cu Kα radiation λ = 1.54180 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 8.577 (1) Å	θ = 6.5–27.0º
b = 13.551 (1) Å	µ = 4.70 mm−1
c = 10.357 (1) Å	T = 296 (2) K
β = 93.04 (1)º	Thick needle, colourless
V = 1202.1 (2) Å3	0.60 × 0.28 × 0.23 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.022
Radiation source: medium-focus sealed tube	θmax = 67.0º
Monochromator: graphite	θmin = 4.3º
T = 296(2) K	h = −10→3
ω–2θ scans	k = −16→0
Absorption correction: ψ scan(North et al., 1968)	l = −12→12
Tmin = 0.265, Tmax = 0.341	3 standard reflections
3088 measured reflections	every 120 min
2249 independent reflections	intensity decay: none
2165 reflections with I > 2˘I)

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046	w = 1/[σ2(Fo2) + (0.0835P)2 + 0.4755P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.131	(Δ/σ)max = 0.010
S = 1.10	Δρmax = 0.37 e Å−3
2249 reflections	Δρmin = −0.49 e Å−3
308 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.0062 (9)
Primary atom site location: structure-invariant direct methods	Absolute structure: No Flack (1983), no Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.07 (2)

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	0.32030 (17)	−0.00289 (12)	−0.13075 (14)	0.0740 (5)
Cl2	1.14912 (18)	0.14458 (13)	0.63527 (15)	0.0799 (5)
O1	0.5608 (3)	0.1667 (2)	0.2587 (3)	0.0503 (8)
N1	0.7425 (4)	0.0481 (3)	0.2308 (4)	0.0460 (8)
H1N	0.8369	0.0308	0.2520	0.055*
C1	0.6552 (5)	−0.0173 (3)	0.1482 (4)	0.0431 (10)
C2	0.5418 (5)	0.0182 (4)	0.0581 (4)	0.0456 (10)
H2	0.5206	0.0853	0.0511	0.055*
C3	0.4622 (5)	−0.0494 (4)	−0.0200 (4)	0.0445 (10)
C4	0.4926 (6)	−0.1489 (4)	−0.0152 (5)	0.0515 (11)
H4	0.4385	−0.1926	−0.0703	0.062*
C5	0.6063 (6)	−0.1817 (4)	0.0742 (4)	0.0535 (11)
H5	0.6279	−0.2489	0.0807	0.064*
C6	0.6879 (5)	−0.1163 (4)	0.1537 (4)	0.0488 (10)
H6	0.7660	−0.1394	0.2117	0.059*
C7	0.6948 (4)	0.1331 (3)	0.2792 (4)	0.0422 (9)
C8	0.8119 (4)	0.1892 (4)	0.3622 (4)	0.0393 (9)
C9	0.9189 (5)	0.1425 (4)	0.4483 (4)	0.0441 (9)
H9	0.9228	0.0741	0.4541	0.053*
C10	1.0191 (5)	0.2006 (4)	0.5251 (4)	0.0459 (10)
C11	1.0193 (6)	0.3013 (4)	0.5145 (5)	0.0485 (10)
H11	1.0898	0.3389	0.5649	0.058*
C12	0.9142 (5)	0.3464 (4)	0.4286 (5)	0.0496 (11)
H12	0.9139	0.4148	0.4208	0.060*
C13	0.8099 (5)	0.2910 (4)	0.3546 (4)	0.0456 (10)
H13	0.7371	0.3222	0.2987	0.055*
Cl3	0.1457 (2)	0.46405 (11)	0.18206 (16)	0.0753 (4)
Cl4	0.39972 (18)	−0.34554 (10)	0.31885 (16)	0.0731 (4)
O2	0.0590 (3)	−0.0229 (2)	0.2416 (3)	0.0517 (8)
N2	0.2432 (4)	0.0962 (3)	0.2377 (4)	0.0485 (9)
H2N	0.3378	0.1108	0.2621	0.058*
C14	0.1548 (5)	0.1709 (3)	0.1702 (4)	0.0428 (10)
C15	0.1861 (5)	0.2671 (4)	0.2042 (4)	0.0465 (10)
H15	0.2607	0.2819	0.2697	0.056*
C16	0.1049 (6)	0.3412 (4)	0.1395 (5)	0.0502 (11)
C17	−0.0064 (6)	0.3217 (4)	0.0413 (5)	0.0576 (12)
H17	−0.0604	0.3727	−0.0011	0.069*
C18	−0.0353 (6)	0.2251 (4)	0.0079 (5)	0.0604 (13)
H18	−0.1089	0.2106	−0.0585	0.072*
C19	0.0435 (6)	0.1493 (4)	0.0719 (4)	0.0532 (10)
H19	0.0222	0.0841	0.0493	0.064*
C20	0.1947 (5)	0.0069 (3)	0.2667 (4)	0.0433 (9)
C21	0.3143 (5)	−0.0594 (3)	0.3333 (4)	0.0425 (9)
C22	0.3057 (5)	−0.1578 (4)	0.3017 (4)	0.0425 (10)
H22	0.2313	−0.1802	0.2400	0.051*
C23	0.4090 (5)	−0.2227 (3)	0.3627 (4)	0.0464 (10)
C24	0.5166 (5)	−0.1926 (4)	0.4561 (5)	0.0518 (11)
H24	0.5846	−0.2378	0.4966	0.062*
C25	0.5229 (6)	−0.0953 (4)	0.4891 (5)	0.0560 (12)
H25	0.5951	−0.0742	0.5535	0.067*
C26	0.4227 (5)	−0.0268 (4)	0.4277 (4)	0.0477 (10)
H26	0.4286	0.0397	0.4498	0.057*

	U11	U22	U33	U12	U13	U23
Cl1	0.0702 (8)	0.0747 (9)	0.0728 (8)	−0.0055 (7)	−0.0370 (6)	0.0012 (7)
Cl2	0.0704 (8)	0.0792 (10)	0.0852 (10)	−0.0037 (8)	−0.0431 (7)	0.0120 (8)
O1	0.0270 (13)	0.052 (2)	0.0705 (19)	0.0027 (12)	−0.0092 (12)	−0.0101 (15)
N1	0.0294 (16)	0.051 (2)	0.056 (2)	0.0007 (15)	−0.0091 (14)	−0.0052 (18)
C1	0.0343 (19)	0.048 (3)	0.046 (2)	−0.0029 (18)	0.0001 (16)	−0.0051 (19)
C2	0.042 (2)	0.045 (2)	0.049 (2)	−0.0022 (18)	−0.0042 (17)	−0.0010 (19)
C3	0.034 (2)	0.056 (3)	0.042 (2)	−0.0049 (19)	−0.0059 (17)	−0.004 (2)
C4	0.047 (2)	0.059 (3)	0.048 (2)	−0.011 (2)	−0.0056 (19)	−0.009 (2)
C5	0.060 (3)	0.046 (3)	0.055 (3)	0.003 (2)	0.003 (2)	−0.006 (2)
C6	0.042 (2)	0.061 (3)	0.042 (2)	0.000 (2)	−0.0042 (17)	−0.001 (2)
C7	0.0293 (18)	0.050 (3)	0.047 (2)	−0.0013 (18)	−0.0030 (15)	0.0009 (19)
C8	0.0307 (18)	0.048 (2)	0.0391 (19)	−0.0065 (17)	−0.0021 (15)	−0.0006 (17)
C9	0.041 (2)	0.042 (2)	0.048 (2)	−0.0057 (19)	−0.0043 (17)	0.0012 (19)
C10	0.037 (2)	0.057 (3)	0.043 (2)	0.0004 (19)	−0.0072 (16)	0.002 (2)
C11	0.047 (2)	0.052 (3)	0.047 (2)	−0.010 (2)	−0.0028 (18)	−0.011 (2)
C12	0.049 (3)	0.041 (2)	0.058 (3)	−0.0035 (19)	0.003 (2)	−0.006 (2)
C13	0.039 (2)	0.049 (3)	0.049 (2)	0.0023 (18)	0.0013 (17)	0.002 (2)
Cl3	0.0863 (10)	0.0465 (7)	0.0935 (10)	0.0010 (7)	0.0074 (8)	0.0058 (7)
Cl4	0.0804 (8)	0.0452 (7)	0.0932 (10)	0.0119 (6)	0.0009 (7)	−0.0068 (7)
O2	0.0252 (13)	0.0485 (18)	0.080 (2)	−0.0024 (13)	−0.0067 (12)	0.0044 (16)
N2	0.0358 (19)	0.047 (2)	0.062 (2)	0.0023 (16)	−0.0041 (16)	0.0028 (19)
C14	0.0340 (19)	0.049 (3)	0.046 (2)	0.0101 (17)	0.0044 (16)	0.0074 (19)
C15	0.040 (2)	0.049 (3)	0.051 (2)	0.0023 (19)	0.0038 (18)	0.0041 (19)
C16	0.049 (2)	0.044 (3)	0.059 (3)	0.0066 (19)	0.009 (2)	0.005 (2)
C17	0.051 (3)	0.062 (3)	0.059 (3)	0.015 (2)	−0.004 (2)	0.015 (2)
C18	0.053 (3)	0.066 (3)	0.060 (3)	0.007 (2)	−0.015 (2)	0.008 (3)
C19	0.060 (3)	0.049 (2)	0.049 (2)	0.004 (2)	−0.0058 (19)	0.002 (2)
C20	0.038 (2)	0.044 (2)	0.048 (2)	0.0064 (18)	−0.0026 (16)	−0.0033 (19)
C21	0.039 (2)	0.045 (2)	0.043 (2)	0.0084 (18)	0.0011 (16)	0.0008 (18)
C22	0.0335 (19)	0.052 (3)	0.041 (2)	0.0070 (18)	−0.0013 (16)	−0.0019 (18)
C23	0.046 (2)	0.042 (2)	0.051 (2)	0.0043 (19)	0.0058 (18)	0.0039 (19)
C24	0.044 (2)	0.051 (3)	0.060 (3)	0.012 (2)	−0.005 (2)	0.012 (2)
C25	0.047 (3)	0.066 (3)	0.054 (2)	−0.004 (2)	−0.013 (2)	0.004 (2)
C26	0.050 (2)	0.040 (2)	0.052 (2)	0.002 (2)	−0.0029 (18)	0.000 (2)

Cl1—C3	1.745 (4)	Cl3—C16	1.753 (5)
Cl2—C10	1.729 (4)	Cl4—C23	1.726 (5)
O1—C7	1.244 (5)	O2—C20	1.246 (5)
N1—C7	1.330 (6)	N2—C20	1.319 (6)
N1—C1	1.418 (5)	N2—C14	1.425 (5)
N1—H1N	0.8600	N2—H2N	0.8600
C1—C6	1.370 (7)	C14—C15	1.373 (7)
C1—C2	1.397 (6)	C14—C19	1.390 (6)
C2—C3	1.379 (6)	C15—C16	1.376 (7)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.373 (7)	C16—C17	1.383 (7)
C4—C5	1.383 (7)	C17—C18	1.373 (8)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.376 (7)	C18—C19	1.380 (7)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.493 (6)	C20—C21	1.503 (6)
C8—C13	1.382 (6)	C21—C22	1.374 (6)
C8—C9	1.397 (6)	C21—C26	1.386 (6)
C9—C10	1.385 (6)	C22—C23	1.378 (6)
C9—H9	0.9300	C22—H22	0.9300
C10—C11	1.369 (7)	C23—C24	1.363 (7)
C11—C12	1.375 (7)	C24—C25	1.364 (8)
C11—H11	0.9300	C24—H24	0.9300
C12—C13	1.372 (6)	C25—C26	1.395 (7)
C12—H12	0.9300	C25—H25	0.9300
C13—H13	0.9300	C26—H26	0.9300
C7—N1—C1	127.3 (4)	C20—N2—C14	126.6 (4)
C7—N1—H1N	116.3	C20—N2—H2N	116.7
C1—N1—H1N	116.3	C14—N2—H2N	116.7
C6—C1—C2	119.9 (4)	C15—C14—C19	120.3 (4)
C6—C1—N1	119.1 (4)	C15—C14—N2	117.2 (4)
C2—C1—N1	121.0 (4)	C19—C14—N2	122.5 (4)
C3—C2—C1	117.9 (4)	C14—C15—C16	118.8 (4)
C3—C2—H2	121.0	C14—C15—H15	120.6
C1—C2—H2	121.0	C16—C15—H15	120.6
C4—C3—C2	122.9 (5)	C15—C16—C17	122.0 (5)
C4—C3—Cl1	120.2 (4)	C15—C16—Cl3	118.8 (4)
C2—C3—Cl1	116.9 (4)	C17—C16—Cl3	119.2 (4)
C3—C4—C5	117.8 (4)	C18—C17—C16	118.4 (5)
C3—C4—H4	121.1	C18—C17—H17	120.8
C5—C4—H4	121.1	C16—C17—H17	120.8
C6—C5—C4	120.7 (5)	C17—C18—C19	120.8 (5)
C6—C5—H5	119.6	C17—C18—H18	119.6
C4—C5—H5	119.6	C19—C18—H18	119.6
C1—C6—C5	120.6 (4)	C18—C19—C14	119.7 (5)
C1—C6—H6	119.7	C18—C19—H19	120.2
C5—C6—H6	119.7	C14—C19—H19	120.2
O1—C7—N1	123.5 (4)	O2—C20—N2	123.5 (4)
O1—C7—C8	120.0 (4)	O2—C20—C21	120.6 (4)
N1—C7—C8	116.5 (4)	N2—C20—C21	115.9 (4)
C13—C8—C9	119.6 (4)	C22—C21—C26	120.2 (4)
C13—C8—C7	118.0 (4)	C22—C21—C20	116.3 (4)
C9—C8—C7	122.4 (4)	C26—C21—C20	123.3 (4)
C10—C9—C8	118.4 (4)	C21—C22—C23	119.0 (4)
C10—C9—H9	120.8	C21—C22—H22	120.5
C8—C9—H9	120.8	C23—C22—H22	120.5
C11—C10—C9	121.6 (4)	C24—C23—C22	121.9 (5)
C11—C10—Cl2	119.2 (4)	C24—C23—Cl4	119.7 (4)
C9—C10—Cl2	119.2 (4)	C22—C23—Cl4	118.4 (4)
C10—C11—C12	119.4 (5)	C25—C24—C23	118.9 (4)
C10—C11—H11	120.3	C25—C24—H24	120.5
C12—C11—H11	120.3	C23—C24—H24	120.5
C13—C12—C11	120.3 (5)	C24—C25—C26	120.9 (5)
C13—C12—H12	119.9	C24—C25—H25	119.5
C11—C12—H12	119.9	C26—C25—H25	119.5
C12—C13—C8	120.6 (4)	C21—C26—C25	118.9 (5)
C12—C13—H13	119.7	C21—C26—H26	120.5
C8—C13—H13	119.7	C25—C26—H26	120.5
C7—N1—C1—C6	−150.4 (5)	C20—N2—C14—C15	147.2 (5)
C7—N1—C1—C2	32.5 (7)	C20—N2—C14—C19	−34.2 (7)
C6—C1—C2—C3	2.2 (6)	C19—C14—C15—C16	0.3 (6)
N1—C1—C2—C3	179.4 (4)	N2—C14—C15—C16	178.9 (4)
C1—C2—C3—C4	−1.8 (7)	C14—C15—C16—C17	−0.3 (7)
C1—C2—C3—Cl1	179.6 (3)	C14—C15—C16—Cl3	−179.6 (3)
C2—C3—C4—C5	1.3 (7)	C15—C16—C17—C18	−0.3 (8)
Cl1—C3—C4—C5	179.9 (4)	Cl3—C16—C17—C18	179.1 (4)
C3—C4—C5—C6	−1.2 (7)	C16—C17—C18—C19	0.8 (8)
C2—C1—C6—C5	−2.3 (7)	C17—C18—C19—C14	−0.8 (8)
N1—C1—C6—C5	−179.5 (4)	C15—C14—C19—C18	0.2 (7)
C4—C5—C6—C1	1.7 (7)	N2—C14—C19—C18	−178.3 (4)
C1—N1—C7—O1	1.2 (7)	C14—N2—C20—O2	−2.7 (7)
C1—N1—C7—C8	−178.8 (4)	C14—N2—C20—C21	177.2 (4)
O1—C7—C8—C13	−36.2 (6)	O2—C20—C21—C22	35.5 (6)
N1—C7—C8—C13	143.8 (4)	N2—C20—C21—C22	−144.4 (4)
O1—C7—C8—C9	142.1 (4)	O2—C20—C21—C26	−140.5 (4)
N1—C7—C8—C9	−37.9 (6)	N2—C20—C21—C26	39.5 (6)
C13—C8—C9—C10	0.8 (6)	C26—C21—C22—C23	−1.7 (6)
C7—C8—C9—C10	−177.5 (4)	C20—C21—C22—C23	−177.9 (4)
C8—C9—C10—C11	−2.6 (7)	C21—C22—C23—C24	1.9 (7)
C8—C9—C10—Cl2	178.4 (3)	C21—C22—C23—Cl4	−178.4 (3)
C9—C10—C11—C12	2.1 (8)	C22—C23—C24—C25	−0.6 (7)
Cl2—C10—C11—C12	−178.8 (4)	Cl4—C23—C24—C25	179.7 (4)
C10—C11—C12—C13	0.2 (7)	C23—C24—C25—C26	−0.8 (8)
C11—C12—C13—C8	−2.0 (7)	C22—C21—C26—C25	0.3 (6)
C9—C8—C13—C12	1.5 (7)	C20—C21—C26—C25	176.3 (4)
C7—C8—C13—C12	179.8 (4)	C24—C25—C26—C21	0.9 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O2i	0.86	2.05	2.877 (4)	161.7
N2—H2n···O1	0.86	2.06	2.884 (5)	160.5

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O2i	0.86	2.05	2.877 (4)	162
N2—H2n⋯O1	0.86	2.06	2.884 (5)	161

Symmetry code: (i) .