2-Chloro-N-(2-chloro­phen­yl)benzamide

The conformation of the N—H bond in the structure of the title compound, C₁₃H₉Cl₂NO, is syn to the ortho-Cl substituent in the aniline ring, similar to that observed in N-(2,3-dichloro­phen­yl)benzamide with respect to both the ortho-Cl and meta-Cl substituents, but in contrast to the anti conformation observed with respect to the ortho-Cl substituent in N-(2-chloro­phen­yl)benzamide. The bond parameters are similar to those in 2-chloro-N-phenyl­benzamide and other benzanilides. The mol­ecules are linked into chains in the direction of the b axis through N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.078
• wR factor = 0.156
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

In the present work, as part of a study of the substituent effects on the structures of N-aromatic amides (Gowda, Jyothi et al., 2003; Gowda, Sowmya et al., 2007a, b), the structure of N-(2-chlorophenyl)- 2-chlorobenzamide has been determined. The conformation of the N—H bond is syn to the ortho-Cl substituent in the aniline ring (Fig. 1), similar to that observed in N-(2,3-dichlorophenyl)-benzamide (Gowda, Sowmya et al., 2007b) with respect to both the ortho-Cl and meta-Cl substituents, but in contrast to the anti conformation observed with respect to the ortho-Cl substituent in N-(2-chlorophenyl)-benzamide (Gowda, Sowmya et al., 2007a). The bond parameters are similar to those in N-(phenyl)-2-chlorobenzamide (Gowda, Jyothi et al.,2003) and other benzanilides. The crystal packing is characterized by N—H^···O hydrogen bonds (Table 1) leading to chains in the direction of the b axis (Fig. 2).

Related literature

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

S2. Experimental

The title compound was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

S3. Refinement

The H atoms were positioned geometrically and including in the refinement in the riding-model approximation, with C—H = 0.93 Å, N—H = 0.86 Å and with U_iso(H) = 1.2 U_eq of the parent atom.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Molecular packing of the title compound with hydrogen bonds shown as dashed lines.

2-Chloro-N-(2-chlorophenyl)benzamide

Crystal data

C13H9Cl2NO	F(000) = 1088
Mr = 266.11	Dx = 1.455 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6575 reflections
a = 5.9466 (5) Å	θ = 3.0–27.6°
b = 9.8323 (8) Å	µ = 0.52 mm^−1
c = 41.559 (3) Å	T = 299 K
V = 2429.9 (3) Å^3	Prism, colourless
Z = 8	0.50 × 0.50 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur single-crystal X-ray diffractometer with Sapphire CCD detector	2489 independent reflections
Radiation source: fine-focus sealed tube	2116 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Rotation method data acquisition using ω and phi scans.	θmax = 26.4°, θmin = 4.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −7→7
Tmin = 0.777, Tmax = 0.824	k = −12→12
28151 measured reflections	l = −51→51

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.156	H-atom parameters constrained
S = 1.29	w = 1/[σ^2(Fo^2) + (0.0123P)^2 + 6.6653P] where P = (Fo^2 + 2Fc^2)/3
2489 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.0524 (7)	0.1362 (4)	0.15997 (9)	0.0383 (9)
C2	0.0696 (7)	0.0990 (4)	0.19211 (9)	0.0440 (10)
C3	−0.0719 (9)	0.1534 (5)	0.21502 (11)	0.0616 (13)
H3	−0.0573	0.1287	0.2365	0.074*
C4	−0.2344 (10)	0.2444 (6)	0.20579 (12)	0.0677 (14)
H4	−0.3306	0.2805	0.2212	0.081*
C5	−0.2581 (9)	0.2836 (5)	0.17411 (12)	0.0629 (13)
H5	−0.3690	0.3452	0.1681	0.076*
C6	−0.1136 (8)	0.2293 (4)	0.15167 (10)	0.0504 (11)
H6	−0.1274	0.2557	0.1303	0.061*
C7	0.1937 (7)	0.0726 (4)	0.13436 (9)	0.0419 (9)
C8	0.4467 (7)	0.1213 (4)	0.08982 (9)	0.0400 (9)
C9	0.4116 (8)	0.1720 (4)	0.05922 (9)	0.0457 (10)
C10	0.5503 (10)	0.1354 (6)	0.03421 (12)	0.0685 (15)
H10	0.5260	0.1703	0.0137	0.082*
C11	0.7245 (12)	0.0472 (6)	0.03968 (16)	0.0831 (19)
H11	0.8175	0.0215	0.0227	0.100*
C12	0.7632 (10)	−0.0038 (5)	0.07010 (16)	0.0742 (16)
H12	0.8824	−0.0631	0.0738	0.089*
C13	0.6235 (8)	0.0338 (4)	0.09495 (12)	0.0560 (12)
H13	0.6491	−0.0004	0.1155	0.067*
Cl1	0.2734 (3)	−0.01613 (14)	0.20427 (3)	0.0688 (4)
Cl2	0.1935 (2)	0.28517 (14)	0.05234 (3)	0.0700 (4)
N1	0.3050 (6)	0.1613 (3)	0.11571 (7)	0.0430 (8)
H1N	0.2899	0.2467	0.1196	0.052*
O1	0.2008 (6)	−0.0508 (3)	0.13050 (7)	0.0597 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.050 (2)	0.0260 (17)	0.0387 (19)	−0.0059 (17)	0.0031 (18)	−0.0024 (15)
C2	0.051 (2)	0.038 (2)	0.043 (2)	−0.008 (2)	−0.0042 (19)	0.0003 (18)
C3	0.080 (4)	0.064 (3)	0.041 (2)	−0.012 (3)	0.013 (2)	0.000 (2)
C4	0.070 (3)	0.063 (3)	0.071 (3)	0.000 (3)	0.026 (3)	−0.013 (3)
C5	0.063 (3)	0.049 (3)	0.077 (3)	0.010 (3)	0.010 (3)	−0.005 (3)
C6	0.067 (3)	0.035 (2)	0.049 (2)	0.002 (2)	0.000 (2)	0.0049 (19)
C7	0.055 (3)	0.035 (2)	0.036 (2)	−0.0010 (19)	−0.0031 (18)	0.0005 (16)
C8	0.050 (2)	0.0297 (19)	0.041 (2)	−0.0057 (18)	0.0048 (18)	−0.0046 (16)
C9	0.055 (3)	0.041 (2)	0.041 (2)	−0.010 (2)	0.0023 (19)	−0.0036 (17)
C10	0.085 (4)	0.072 (3)	0.048 (3)	−0.021 (3)	0.020 (3)	−0.011 (2)
C11	0.083 (4)	0.079 (4)	0.088 (4)	−0.013 (4)	0.038 (4)	−0.031 (3)
C12	0.060 (3)	0.049 (3)	0.114 (5)	0.007 (3)	0.013 (3)	−0.020 (3)
C13	0.059 (3)	0.038 (2)	0.071 (3)	0.002 (2)	−0.001 (2)	−0.004 (2)
Cl1	0.0846 (9)	0.0649 (8)	0.0569 (7)	0.0116 (7)	−0.0214 (7)	0.0030 (6)
Cl2	0.0795 (9)	0.0737 (8)	0.0568 (7)	0.0097 (7)	−0.0141 (6)	0.0075 (6)
N1	0.062 (2)	0.0271 (15)	0.0403 (17)	0.0003 (16)	0.0064 (16)	−0.0027 (14)
O1	0.090 (3)	0.0259 (14)	0.0635 (19)	−0.0028 (16)	0.0167 (18)	−0.0053 (13)

Geometric parameters (Å, º)

C1—C2	1.389 (5)	C8—C13	1.375 (6)
C1—C6	1.389 (6)	C8—C9	1.382 (5)
C1—C7	1.493 (5)	C8—N1	1.422 (5)
C2—C3	1.379 (6)	C9—C10	1.375 (6)
C2—Cl1	1.734 (4)	C9—Cl2	1.733 (5)
C3—C4	1.372 (7)	C10—C11	1.370 (8)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.379 (7)	C11—C12	1.379 (8)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.376 (6)	C12—C13	1.376 (7)
C5—H5	0.9300	C12—H12	0.9300
C6—H6	0.9300	C13—H13	0.9300
C7—O1	1.225 (5)	N1—H1N	0.8600
C7—N1	1.341 (5)
C2—C1—C6	117.7 (4)	C13—C8—C9	118.9 (4)
C2—C1—C7	122.3 (4)	C13—C8—N1	120.6 (4)
C6—C1—C7	119.9 (4)	C9—C8—N1	120.5 (4)
C3—C2—C1	121.1 (4)	C10—C9—C8	120.7 (5)
C3—C2—Cl1	118.6 (3)	C10—C9—Cl2	119.5 (4)
C1—C2—Cl1	120.3 (3)	C8—C9—Cl2	119.8 (3)
C4—C3—C2	119.3 (4)	C11—C10—C9	119.6 (5)
C4—C3—H3	120.3	C11—C10—H10	120.2
C2—C3—H3	120.3	C9—C10—H10	120.2
C3—C4—C5	121.4 (5)	C10—C11—C12	120.5 (5)
C3—C4—H4	119.3	C10—C11—H11	119.7
C5—C4—H4	119.3	C12—C11—H11	119.7
C6—C5—C4	118.3 (5)	C13—C12—C11	119.3 (5)
C6—C5—H5	120.8	C13—C12—H12	120.3
C4—C5—H5	120.8	C11—C12—H12	120.3
C5—C6—C1	122.1 (4)	C8—C13—C12	120.9 (5)
C5—C6—H6	119.0	C8—C13—H13	119.6
C1—C6—H6	119.0	C12—C13—H13	119.6
O1—C7—N1	123.5 (4)	C7—N1—C8	123.3 (3)
O1—C7—C1	121.8 (4)	C7—N1—H1N	118.3
N1—C7—C1	114.7 (3)	C8—N1—H1N	118.3
C6—C1—C2—C3	−0.5 (6)	C13—C8—C9—C10	0.3 (6)
C7—C1—C2—C3	−176.1 (4)	N1—C8—C9—C10	178.9 (4)
C6—C1—C2—Cl1	−179.8 (3)	C13—C8—C9—Cl2	−178.7 (3)
C7—C1—C2—Cl1	4.6 (5)	N1—C8—C9—Cl2	0.0 (5)
C1—C2—C3—C4	0.9 (7)	C8—C9—C10—C11	0.3 (7)
Cl1—C2—C3—C4	−179.8 (4)	Cl2—C9—C10—C11	179.2 (4)
C2—C3—C4—C5	−0.6 (8)	C9—C10—C11—C12	−0.7 (8)
C3—C4—C5—C6	−0.2 (8)	C10—C11—C12—C13	0.6 (9)
C4—C5—C6—C1	0.6 (7)	C9—C8—C13—C12	−0.4 (6)
C2—C1—C6—C5	−0.2 (6)	N1—C8—C13—C12	−179.1 (4)
C7—C1—C6—C5	175.5 (4)	C11—C12—C13—C8	0.0 (8)
C2—C1—C7—O1	54.3 (6)	O1—C7—N1—C8	−1.2 (7)
C6—C1—C7—O1	−121.2 (5)	C1—C7—N1—C8	−179.4 (4)
C2—C1—C7—N1	−127.5 (4)	C13—C8—N1—C7	−56.3 (6)
C6—C1—C7—N1	57.0 (5)	C9—C8—N1—C7	125.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.86	2.04	2.896 (4)	172

Symmetry code: (i) −x+1/2, y+1/2, z.