N-(3,4-Dichloro­phen­yl)benzamide

The conformation of the N—H bond in the structure of the title compound, C₁₃H₉Cl₂NO, is anti to the meta-chloro substituent in the dichlorophenyl ring, similar to that observed with respect to the meta-chloro substituent in N-(3,4-dichloro­phen­yl)acetamide and ortho-chloro substituent in N-(2-chloro­phen­yl)benzamide, but in contrast to the syn conformation observed with respect to both the ortho-chloro and meta-chloro substituents in N-(2,3-dichloro­phen­yl)benzamide. The bond parameters are similar to those in 2-chloro-N-phenyl­benzamide, N-(2-chloro­phen­yl)benzamide and N-(2,3-dichloro­phen­yl)benzamide. The mol­ecules are packed into chains in the direction of the b axis through N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.033
• wR factor = 0.093
• Data-to-parameter ratio = 15.0

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S1. Comment

In the present work, the structure of N-(3,4-dichlorophenyl)-benzamide has been determined to explore the substituent effects on the structures of N-aromatic amides (Gowda et al., 2003; Gowda, Kozisek et al., 2007; Gowda, Sowmya, Kožíšek et al. 2007; Gowda, Sowmya, Tokarcik et al., 2007). The conformation of the N—H bond (Fig. 1) is anti to the meta-chloro substituent in the aniline phenyl ring, similar to that observed with respect to the meta chloro substituent in N-(3,4-dichlorophenyl)-acetamide (Jones et al., 1990) and ortho chloro substituent in N-(2-chlorophenyl)-benzamide (Gowda, Sowmya, Kožíšek et al. 2007), but in contrast to the syn conformation observed with respect to both the ortho-chloro and meta-chloro substituents in N-(2,3-dichlorophenyl)-benzamide (Gowda, Sowmya, Tokarcik et al., 2007). The bond parameters are similar to those in N-(phenyl)-2-chlorobenzamide (Gowda et al., 2003), N-(2-chlorophenyl)-benzamide (Gowda, Sowmya, Kožíšek et al. 2007) and N-(2,3-dichlorophenyl)-benzamide (Gowda, Sowmya, Tokarcik et al., 2007). Hydrogen bond link the molecules to chains running along the b axis (Fig.2).

Related literature

For related literature, see: Gowda et al. (2003); Gowda, Kozisek et al. (2007); Gowda, Sowmya, Kožíšek et al. (2007); Gowda, Sowmya, Tokarcik et al. (2007); Jones et al. (1990); Clark & Reid (1995).

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

H atoms were seen in difference map and refined using a riding model with C–H distances 0.93Å for the ring hydrogen atoms, 0.86Å for the H(N) atom, and with U_iso(H) = 1.2 U_eq(C) for all H atoms.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); 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).

Figures

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Part of crystal structure of the title; hydrogen bonds shown as dashes lines. H atoms not involved in hydrogen bonding have been omitted. Symmetry code (i): x, y - 1, z.

N-(3,4-Dichlorophenyl)benzamide

Crystal data

C13H9Cl2NO	F(000) = 544
Mr = 266.11	Dx = 1.498 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7847 reflections
a = 11.2828 (2) Å	θ = 3.6–29.5°
b = 5.1400 (1) Å	µ = 0.53 mm^−1
c = 20.9368 (5) Å	T = 295 K
β = 103.657 (2)°	Prism, colorless
V = 1179.87 (4) Å^3	0.32 × 0.09 × 0.05 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur System diffractometer	2316 independent reflections
Graphite monochromator	1788 reflections with I > 2σ(I)
Detector resolution: 10.4340 pixels mm^-1	Rint = 0.025
ω scans with κ offsets	θmax = 26.0°, θmin = 4.1°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006)	h = −13→13
Tmin = 0.811, Tmax = 0.963	k = −5→6
18488 measured reflections	l = −25→25

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)] = 0.033	Hydrogen site location: difference Fourier map
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.043P)^2 + 0.3587P] where P = (Fo^2 + 2Fc^2)/3
2316 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.24 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	−0.06707 (16)	0.6618 (3)	0.07436 (9)	0.0408 (4)
C2	−0.17812 (16)	0.6102 (3)	0.02116 (9)	0.0403 (4)
C3	−0.20601 (19)	0.7783 (4)	−0.03154 (10)	0.0517 (5)
H3	−0.1533	0.9145	−0.0345	0.062*
C4	−0.3116 (2)	0.7460 (5)	−0.07990 (11)	0.0657 (6)
H4	−0.3293	0.8602	−0.1153	0.079*
C5	−0.3899 (2)	0.5489 (5)	−0.07623 (11)	0.0650 (6)
H5	−0.4607	0.5277	−0.1092	0.078*
C6	−0.3641 (2)	0.3810 (4)	−0.02368 (12)	0.0662 (6)
H6	−0.4181	0.2474	−0.0208	0.079*
C7	−0.25851 (19)	0.4096 (4)	0.02470 (11)	0.0557 (5)
H7	−0.2411	0.2941	0.0599	0.067*
C8	0.07957 (16)	0.4545 (3)	0.16650 (9)	0.0400 (4)
C9	0.17486 (16)	0.6320 (3)	0.17660 (9)	0.0437 (4)
H9	0.1784	0.7555	0.1446	0.052*
C10	0.26459 (16)	0.6244 (3)	0.23455 (9)	0.0446 (4)
C11	0.25928 (17)	0.4446 (4)	0.28304 (9)	0.0452 (4)
C12	0.16527 (18)	0.2642 (4)	0.27169 (10)	0.0498 (5)
H12	0.1622	0.1393	0.3034	0.06*
C13	0.07682 (17)	0.2684 (4)	0.21419 (9)	0.0455 (4)
H13	0.0145	0.1457	0.2071	0.055*
N1	−0.01460 (13)	0.4513 (3)	0.10875 (7)	0.0438 (4)
H1	−0.0414	0.3012	0.0939	0.053*
O1	−0.02755 (13)	0.8827 (2)	0.08692 (7)	0.0553 (4)
Cl1	0.38564 (5)	0.83887 (10)	0.24432 (3)	0.06298 (19)
Cl2	0.36741 (5)	0.43840 (12)	0.35648 (3)	0.0683 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0444 (10)	0.0324 (9)	0.0443 (10)	−0.0021 (8)	0.0079 (8)	−0.0013 (7)
C2	0.0415 (10)	0.0337 (9)	0.0444 (10)	0.0007 (7)	0.0077 (8)	−0.0044 (7)
C3	0.0554 (12)	0.0465 (11)	0.0502 (11)	−0.0031 (9)	0.0065 (9)	0.0026 (9)
C4	0.0719 (15)	0.0642 (14)	0.0517 (12)	0.0027 (12)	−0.0041 (11)	0.0066 (11)
C5	0.0529 (13)	0.0624 (14)	0.0672 (14)	0.0036 (11)	−0.0109 (10)	−0.0110 (11)
C6	0.0482 (12)	0.0563 (13)	0.0852 (16)	−0.0118 (10)	−0.0021 (11)	−0.0018 (12)
C7	0.0500 (12)	0.0441 (11)	0.0668 (13)	−0.0064 (9)	0.0014 (10)	0.0067 (10)
C8	0.0421 (10)	0.0300 (9)	0.0465 (10)	0.0025 (7)	0.0077 (8)	−0.0030 (7)
C9	0.0420 (10)	0.0341 (10)	0.0526 (11)	−0.0001 (8)	0.0062 (8)	0.0035 (8)
C10	0.0384 (10)	0.0367 (10)	0.0566 (11)	0.0008 (8)	0.0071 (8)	−0.0052 (8)
C11	0.0433 (10)	0.0433 (10)	0.0466 (10)	0.0094 (8)	0.0056 (8)	−0.0033 (8)
C12	0.0537 (12)	0.0437 (11)	0.0518 (11)	0.0047 (9)	0.0121 (9)	0.0070 (9)
C13	0.0468 (11)	0.0339 (10)	0.0550 (11)	−0.0028 (8)	0.0106 (9)	−0.0001 (8)
N1	0.0454 (9)	0.0276 (7)	0.0529 (9)	−0.0039 (6)	0.0008 (7)	−0.0025 (6)
O1	0.0621 (9)	0.0302 (7)	0.0630 (8)	−0.0058 (6)	−0.0065 (7)	0.0000 (6)
Cl1	0.0441 (3)	0.0544 (3)	0.0815 (4)	−0.0097 (2)	−0.0030 (2)	0.0019 (3)
Cl2	0.0620 (4)	0.0785 (4)	0.0540 (3)	0.0084 (3)	−0.0070 (2)	−0.0007 (3)

Geometric parameters (Å, º)

C1—O1	1.225 (2)	C8—C9	1.388 (2)
C1—N1	1.356 (2)	C8—C13	1.388 (3)
C1—C2	1.491 (2)	C8—N1	1.409 (2)
C2—C3	1.378 (3)	C9—C10	1.385 (3)
C2—C7	1.387 (3)	C9—H9	0.93
C3—C4	1.379 (3)	C10—C11	1.384 (3)
C3—H3	0.93	C10—Cl1	1.7293 (18)
C4—C5	1.358 (3)	C11—C12	1.387 (3)
C4—H4	0.93	C11—Cl2	1.7228 (19)
C5—C6	1.375 (3)	C12—C13	1.371 (3)
C5—H5	0.93	C12—H12	0.93
C6—C7	1.377 (3)	C13—H13	0.93
C6—H6	0.93	N1—H1	0.86
C7—H7	0.93
O1—C1—N1	122.29 (16)	C9—C8—C13	119.44 (16)
O1—C1—C2	121.63 (16)	C9—C8—N1	122.58 (16)
N1—C1—C2	116.07 (14)	C13—C8—N1	117.97 (16)
C3—C2—C7	118.71 (17)	C10—C9—C8	119.65 (17)
C3—C2—C1	118.64 (16)	C10—C9—H9	120.2
C7—C2—C1	122.51 (16)	C8—C9—H9	120.2
C2—C3—C4	120.44 (19)	C11—C10—C9	120.79 (17)
C2—C3—H3	119.8	C11—C10—Cl1	120.56 (15)
C4—C3—H3	119.8	C9—C10—Cl1	118.63 (14)
C5—C4—C3	120.6 (2)	C10—C11—C12	118.98 (17)
C5—C4—H4	119.7	C10—C11—Cl2	121.52 (15)
C3—C4—H4	119.7	C12—C11—Cl2	119.50 (15)
C4—C5—C6	119.8 (2)	C13—C12—C11	120.59 (18)
C4—C5—H5	120.1	C13—C12—H12	119.7
C6—C5—H5	120.1	C11—C12—H12	119.7
C5—C6—C7	120.3 (2)	C12—C13—C8	120.48 (17)
C5—C6—H6	119.9	C12—C13—H13	119.8
C7—C6—H6	119.9	C8—C13—H13	119.8
C6—C7—C2	120.2 (2)	C1—N1—C8	126.38 (14)
C6—C7—H7	119.9	C1—N1—H1	116.8
C2—C7—H7	119.9	C8—N1—H1	116.8
O1—C1—C2—C3	28.3 (3)	C8—C9—C10—Cl1	177.27 (14)
N1—C1—C2—C3	−153.17 (17)	C9—C10—C11—C12	2.7 (3)
O1—C1—C2—C7	−147.4 (2)	Cl1—C10—C11—C12	−175.68 (14)
N1—C1—C2—C7	31.1 (3)	C9—C10—C11—Cl2	−177.98 (14)
C7—C2—C3—C4	−0.4 (3)	Cl1—C10—C11—Cl2	3.6 (2)
C1—C2—C3—C4	−176.28 (18)	C10—C11—C12—C13	−1.9 (3)
C2—C3—C4—C5	0.3 (3)	Cl2—C11—C12—C13	178.72 (15)
C3—C4—C5—C6	0.4 (4)	C11—C12—C13—C8	−0.4 (3)
C4—C5—C6—C7	−0.9 (4)	C9—C8—C13—C12	1.9 (3)
C5—C6—C7—C2	0.8 (3)	N1—C8—C13—C12	−179.20 (17)
C3—C2—C7—C6	−0.1 (3)	O1—C1—N1—C8	8.0 (3)
C1—C2—C7—C6	175.59 (19)	C2—C1—N1—C8	−170.51 (16)
C13—C8—C9—C10	−1.2 (3)	C9—C8—N1—C1	−37.6 (3)
N1—C8—C9—C10	−179.99 (16)	C13—C8—N1—C1	143.61 (18)
C8—C9—C10—C11	−1.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.86	2.16	2.9568 (19)	153

Symmetry code: (i) x, y−1, z.