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Acta Cryst. (2007). E63, o3365    [ doi:10.1107/S1600536807031571 ]

N-(3,4-Dichlorophenyl)benzamide

B. T. Gowda, B. P. Sowmya, M. Tokarcík, J. Kozísek and H. Fuess

Abstract top

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.

Comment top

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 top

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).

Experimental top

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.

Refinement top

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 Uiso(H) = 1.2 Ueq(C) for all H atoms.

Computing details top

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 top
[Figure 1] 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.
[Figure 2] 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 top
Crystal data top
C13H9Cl2NOF(000) = 544
Mr = 266.11Dx = 1.498 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7847 reflections
a = 11.2828 (2) Åθ = 3.6–29.5°
b = 5.1400 (1) ŵ = 0.53 mm−1
c = 20.9368 (5) ÅT = 295 K
β = 103.657 (2)°Prism, colorless
V = 1179.87 (4) Å30.32 × 0.09 × 0.05 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur System
diffractometer		2316 independent reflections
graphite1788 reflections with I > 2σ(I)
Detector resolution: 10.4340 pixels mm-1Rint = 0.025
ω scans with κ offsetsθmax = 26.0°, θmin = 4.1°
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2006)		h = −13→13
Tmin = 0.811, Tmax = 0.963k = −5→6
18488 measured reflectionsl = −25→25
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: difference Fourier map
wR(F2) = 0.093H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.043P)2 + 0.3587P]
where P = (Fo2 + 2Fc2)/3
2316 reflections(Δ/σ)max = 0.001
154 parametersΔρmax = 0.18 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C13H9Cl2NOV = 1179.87 (4) Å3
Mr = 266.11Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.2828 (2) ŵ = 0.53 mm−1
b = 5.1400 (1) ÅT = 295 K
c = 20.9368 (5) Å0.32 × 0.09 × 0.05 mm
β = 103.657 (2)°
Data collection top
Oxford Diffraction Xcalibur System
diffractometer		2316 independent reflections
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2006)		1788 reflections with I > 2σ(I)
Tmin = 0.811, Tmax = 0.963Rint = 0.025
18488 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.093Δρmax = 0.18 e Å−3
S = 1.07Δρmin = −0.24 e Å−3
2316 reflectionsAbsolute structure: ?
154 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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 (Å2) top
xyzUiso*/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)
H3−0.15330.9145−0.03450.062*
C4−0.3116 (2)0.7460 (5)−0.07990 (11)0.0657 (6)
H4−0.32930.8602−0.11530.079*
C5−0.3899 (2)0.5489 (5)−0.07623 (11)0.0650 (6)
H5−0.46070.5277−0.10920.078*
C6−0.3641 (2)0.3810 (4)−0.02368 (12)0.0662 (6)
H6−0.41810.2474−0.02080.079*
C7−0.25851 (19)0.4096 (4)0.02470 (11)0.0557 (5)
H7−0.24110.29410.05990.067*
C80.07957 (16)0.4545 (3)0.16650 (9)0.0400 (4)
C90.17486 (16)0.6320 (3)0.17660 (9)0.0437 (4)
H90.17840.75550.14460.052*
C100.26459 (16)0.6244 (3)0.23455 (9)0.0446 (4)
C110.25928 (17)0.4446 (4)0.28304 (9)0.0452 (4)
C120.16527 (18)0.2642 (4)0.27169 (10)0.0498 (5)
H120.16220.13930.30340.06*
C130.07682 (17)0.2684 (4)0.21419 (9)0.0455 (4)
H130.01450.14570.20710.055*
N1−0.01460 (13)0.4513 (3)0.10875 (7)0.0438 (4)
H1−0.04140.30120.09390.053*
O1−0.02755 (13)0.8827 (2)0.08692 (7)0.0553 (4)
Cl10.38564 (5)0.83887 (10)0.24432 (3)0.06298 (19)
Cl20.36741 (5)0.43840 (12)0.35648 (3)0.0683 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0444 (10)0.0324 (9)0.0443 (10)−0.0021 (8)0.0079 (8)−0.0013 (7)
C20.0415 (10)0.0337 (9)0.0444 (10)0.0007 (7)0.0077 (8)−0.0044 (7)
C30.0554 (12)0.0465 (11)0.0502 (11)−0.0031 (9)0.0065 (9)0.0026 (9)
C40.0719 (15)0.0642 (14)0.0517 (12)0.0027 (12)−0.0041 (11)0.0066 (11)
C50.0529 (13)0.0624 (14)0.0672 (14)0.0036 (11)−0.0109 (10)−0.0110 (11)
C60.0482 (12)0.0563 (13)0.0852 (16)−0.0118 (10)−0.0021 (11)−0.0018 (12)
C70.0500 (12)0.0441 (11)0.0668 (13)−0.0064 (9)0.0014 (10)0.0067 (10)
C80.0421 (10)0.0300 (9)0.0465 (10)0.0025 (7)0.0077 (8)−0.0030 (7)
C90.0420 (10)0.0341 (10)0.0526 (11)−0.0001 (8)0.0062 (8)0.0035 (8)
C100.0384 (10)0.0367 (10)0.0566 (11)0.0008 (8)0.0071 (8)−0.0052 (8)
C110.0433 (10)0.0433 (10)0.0466 (10)0.0094 (8)0.0056 (8)−0.0033 (8)
C120.0537 (12)0.0437 (11)0.0518 (11)0.0047 (9)0.0121 (9)0.0070 (9)
C130.0468 (11)0.0339 (10)0.0550 (11)−0.0028 (8)0.0106 (9)−0.0001 (8)
N10.0454 (9)0.0276 (7)0.0529 (9)−0.0039 (6)0.0008 (7)−0.0025 (6)
O10.0621 (9)0.0302 (7)0.0630 (8)−0.0058 (6)−0.0065 (7)0.0000 (6)
Cl10.0441 (3)0.0544 (3)0.0815 (4)−0.0097 (2)−0.0030 (2)0.0019 (3)
Cl20.0620 (4)0.0785 (4)0.0540 (3)0.0084 (3)−0.0070 (2)−0.0007 (3)
Geometric parameters (Å, °) top
C1—O11.225 (2)C8—C91.388 (2)
C1—N11.356 (2)C8—C131.388 (3)
C1—C21.491 (2)C8—N11.409 (2)
C2—C31.378 (3)C9—C101.385 (3)
C2—C71.387 (3)C9—H90.93
C3—C41.379 (3)C10—C111.384 (3)
C3—H30.93C10—Cl11.7293 (18)
C4—C51.358 (3)C11—C121.387 (3)
C4—H40.93C11—Cl21.7228 (19)
C5—C61.375 (3)C12—C131.371 (3)
C5—H50.93C12—H120.93
C6—C71.377 (3)C13—H130.93
C6—H60.93N1—H10.86
C7—H70.93
O1—C1—N1122.29 (16)C9—C8—C13119.44 (16)
O1—C1—C2121.63 (16)C9—C8—N1122.58 (16)
N1—C1—C2116.07 (14)C13—C8—N1117.97 (16)
C3—C2—C7118.71 (17)C10—C9—C8119.65 (17)
C3—C2—C1118.64 (16)C10—C9—H9120.2
C7—C2—C1122.51 (16)C8—C9—H9120.2
C2—C3—C4120.44 (19)C11—C10—C9120.79 (17)
C2—C3—H3119.8C11—C10—Cl1120.56 (15)
C4—C3—H3119.8C9—C10—Cl1118.63 (14)
C5—C4—C3120.6 (2)C10—C11—C12118.98 (17)
C5—C4—H4119.7C10—C11—Cl2121.52 (15)
C3—C4—H4119.7C12—C11—Cl2119.50 (15)
C4—C5—C6119.8 (2)C13—C12—C11120.59 (18)
C4—C5—H5120.1C13—C12—H12119.7
C6—C5—H5120.1C11—C12—H12119.7
C5—C6—C7120.3 (2)C12—C13—C8120.48 (17)
C5—C6—H6119.9C12—C13—H13119.8
C7—C6—H6119.9C8—C13—H13119.8
C6—C7—C2120.2 (2)C1—N1—C8126.38 (14)
C6—C7—H7119.9C1—N1—H1116.8
C2—C7—H7119.9C8—N1—H1116.8
O1—C1—C2—C328.3 (3)C8—C9—C10—Cl1177.27 (14)
N1—C1—C2—C3−153.17 (17)C9—C10—C11—C122.7 (3)
O1—C1—C2—C7−147.4 (2)Cl1—C10—C11—C12−175.68 (14)
N1—C1—C2—C731.1 (3)C9—C10—C11—Cl2−177.98 (14)
C7—C2—C3—C4−0.4 (3)Cl1—C10—C11—Cl23.6 (2)
C1—C2—C3—C4−176.28 (18)C10—C11—C12—C13−1.9 (3)
C2—C3—C4—C50.3 (3)Cl2—C11—C12—C13178.72 (15)
C3—C4—C5—C60.4 (4)C11—C12—C13—C8−0.4 (3)
C4—C5—C6—C7−0.9 (4)C9—C8—C13—C121.9 (3)
C5—C6—C7—C20.8 (3)N1—C8—C13—C12−179.20 (17)
C3—C2—C7—C6−0.1 (3)O1—C1—N1—C88.0 (3)
C1—C2—C7—C6175.59 (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—C1143.61 (18)
C8—C9—C10—C11−1.1 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.162.9568 (19)153
Symmetry codes: (i) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.162.9568 (19)153
Symmetry codes: (i) x, y−1, z.
Acknowledgements top

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany for extensions of his research fellowship. MT and JK thank the Grant Agency of the Slovak Republic (grant No. 1/2449/05).

references
References top

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