organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
*Correspondence e-mail: gowdabt@yahoo.com

(Received 9 November 2011; accepted 1 December 2011; online 7 December 2011)

In the title compound, C13H9Cl2NO, the meta-Cl atom in the benzoyl ring is positioned anti to the C=O bond, while the ortho-Cl atom in the aniline ring is positioned syn to the N—H bond. The two aromatic rings are almost coplanar, making a dihedral angle of 4.73 (5)°. The crystal structure is stabilized by N—H⋯O hydrogen bonds, which link the mol­ecules into chains along the b axis.

Related literature

For the preparation of the title compound, see: Gowda et al. (2008[Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o949.]). For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2000[Gowda, B. T., Paulus, H. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 791-800.], 2008[Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o949.]); Bowes et al. (2003[Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1-o3.]); Saeed et al. (2010[Saeed, A., Arshad, M. & Simpson, J. (2010). Acta Cryst. E66, o2808-o2809.]), on N-(ar­yl)-methane­sulfonamides, see: Jayalakshmi & Gowda (2004[Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491-500.]), on N-(ar­yl)-aryl­sulfonamides, see: Shetty & Gowda (2005[Shetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113-120.]) and on N-chloro­aryl­amides, see: Gowda et al. (1996[Gowda, B. T., Dou, S. & Weiss, A. (1996). Z. Naturforsch. Teil A, 51, 627-636.]).

[Scheme 1]

Experimental

Crystal data
  • C13H9Cl2NO

  • Mr = 266.11

  • Monoclinic, P 21 /n

  • a = 11.1371 (4) Å

  • b = 4.85230 (17) Å

  • c = 21.5198 (8) Å

  • β = 90.142 (3)°

  • V = 1162.94 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.54 mm−1

  • T = 293 K

  • 0.66 × 0.30 × 0.08 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer

  • Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]), based on expressions derived by Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.824, Tmax = 0.958

  • 22845 measured reflections

  • 3262 independent reflections

  • 2279 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.118

  • S = 1.07

  • 3262 reflections

  • 154 parameters

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O1i 0.86 2.14 2.9157 (17) 151
Symmetry code: (i) x, y+1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2002[Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]).

Supporting information


Comment top

The amide and sulfonamide moieties are the constituents of many biologically significant compounds. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2000, 2008; Bowes et al., 2003; Saeed et al., 2010), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005) and N-chloro-arylamides (Gowda et al., 1996), in the present work, the crystal structure of 3-Chloro-N-(2-chlorophenyl)benzamide (I) has been determined (Fig.1).

In (I), the meta-Cl atom in the benzoyl ring is positioned anti to the C=O bond, while the ortho-Cl group in the anilino ring is positioned syn to the N—H bond, the N—H and C=O bonds in the C—NH—C(O)—C segment being anti to each other.

Further, the two aromatic rings are nearly coplanar with the dihedral angle of 4.73 (5)°, compared to the values of 9.1 (2)° and 7.3 (3)° in the two independent molecules of 3-chloro-N-(3-chlorophenyl)benzamide (Gowda et al., 2008).

In the crystal structure, intermolecular N—H···O hydrogen bonds link the molecules into infinite chains running along the a-axis. Part of the crystal structure is shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Gowda et al. (2008). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2000, 2008); Bowes et al. (2003); Saeed et al. (2010), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004), on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005) and on N-chloroarylamides, see: Gowda et al. (1996).

Experimental top

The title compound was prepared according to the method described by Gowda et al. (2008). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra.

Rod like colorless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of an ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.

Refinement top

All H atoms were visible in difference maps and then treated as riding atoms with C–H distances of 0.93Å (C-aromatic) and N—H = 0.86 Å. The Uiso(H) values were set at 1.2 Ueq(C-aromatic, N).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2002); software used to prepare material for publication: enCIFer (Allen et al., 2004).

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 the crystal structure of the title compound. Molecular chains are generated by N—H···O hydrogen bonds which are shown by dashed lines.
3-Chloro-N-(2-chlorophenyl)benzamide top
Crystal data top
C13H9Cl2NOF(000) = 544
Mr = 266.11Dx = 1.520 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 11869 reflections
a = 11.1371 (4) Åθ = 3.4–29.6°
b = 4.85230 (17) ŵ = 0.54 mm1
c = 21.5198 (8) ÅT = 293 K
β = 90.142 (3)°Rod, colorless
V = 1162.94 (7) Å30.66 × 0.30 × 0.08 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer
3262 independent reflections
Radiation source: Enhance (Mo) X-ray Source2279 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 10.4340 pixels mm-1θmax = 29.6°, θmin = 3.4°
ω scansh = 1515
Absorption correction: analytical
[CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]
k = 66
Tmin = 0.824, Tmax = 0.958l = 2929
22845 measured reflections
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0694P)2 + 0.1106P]
where P = (Fo2 + 2Fc2)/3
3262 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C13H9Cl2NOV = 1162.94 (7) Å3
Mr = 266.11Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.1371 (4) ŵ = 0.54 mm1
b = 4.85230 (17) ÅT = 293 K
c = 21.5198 (8) Å0.66 × 0.30 × 0.08 mm
β = 90.142 (3)°
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer
3262 independent reflections
Absorption correction: analytical
[CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]
2279 reflections with I > 2σ(I)
Tmin = 0.824, Tmax = 0.958Rint = 0.034
22845 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 1.07Δρmax = 0.31 e Å3
3262 reflectionsΔρmin = 0.26 e Å3
154 parameters
Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived (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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.28710 (14)0.3142 (3)0.01071 (8)0.0380 (4)
C20.34075 (14)0.4188 (3)0.04824 (7)0.0375 (3)
C30.28456 (14)0.6171 (3)0.08504 (7)0.0376 (3)
H3A0.21150.69300.07310.045*
C40.33904 (15)0.6991 (3)0.13953 (7)0.0389 (4)
C50.44901 (16)0.5933 (4)0.15784 (8)0.0454 (4)
H5A0.48540.65370.19420.055*
C60.50336 (16)0.3967 (4)0.12103 (9)0.0476 (4)
H6A0.57720.32400.13270.057*
C70.44943 (15)0.3067 (3)0.06703 (8)0.0421 (4)
H7A0.48600.17050.04320.050*
C80.16652 (14)0.4468 (3)0.10141 (7)0.0363 (3)
C90.05966 (15)0.5829 (3)0.11471 (7)0.0380 (4)
C100.00095 (17)0.5387 (4)0.16973 (9)0.0498 (4)
H10A0.07190.63280.17780.060*
C110.04410 (19)0.3552 (4)0.21236 (9)0.0553 (5)
H11A0.00320.32350.24930.066*
C120.15079 (18)0.2166 (4)0.20030 (9)0.0518 (5)
H12A0.18160.09250.22920.062*
C130.21073 (16)0.2639 (4)0.14537 (8)0.0450 (4)
H13A0.28230.17130.13760.054*
N10.22659 (12)0.5014 (3)0.04507 (6)0.0378 (3)
H1A0.22450.66790.03140.045*
O10.29906 (12)0.0726 (2)0.02617 (6)0.0521 (3)
Cl10.00096 (4)0.81078 (10)0.06110 (2)0.05256 (16)
Cl20.26902 (4)0.94011 (10)0.18730 (2)0.05402 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0412 (8)0.0296 (8)0.0432 (9)0.0022 (6)0.0019 (7)0.0005 (6)
C20.0435 (8)0.0289 (7)0.0400 (8)0.0024 (6)0.0023 (7)0.0034 (6)
C30.0408 (8)0.0315 (7)0.0406 (8)0.0012 (6)0.0042 (7)0.0026 (6)
C40.0462 (9)0.0320 (8)0.0384 (8)0.0015 (7)0.0005 (7)0.0016 (6)
C50.0499 (9)0.0456 (9)0.0409 (9)0.0042 (8)0.0093 (7)0.0007 (7)
C60.0416 (9)0.0484 (10)0.0529 (10)0.0025 (8)0.0084 (8)0.0044 (8)
C70.0432 (9)0.0381 (9)0.0448 (9)0.0036 (7)0.0002 (7)0.0020 (7)
C80.0407 (8)0.0285 (7)0.0397 (8)0.0044 (6)0.0024 (6)0.0018 (6)
C90.0422 (8)0.0317 (8)0.0402 (8)0.0002 (7)0.0001 (7)0.0034 (6)
C100.0500 (10)0.0503 (10)0.0492 (10)0.0021 (8)0.0120 (8)0.0012 (8)
C110.0672 (12)0.0553 (11)0.0435 (10)0.0023 (10)0.0150 (9)0.0090 (8)
C120.0654 (12)0.0467 (10)0.0433 (10)0.0013 (9)0.0004 (8)0.0110 (8)
C130.0477 (9)0.0392 (8)0.0481 (10)0.0041 (7)0.0003 (7)0.0070 (7)
N10.0467 (7)0.0268 (6)0.0398 (7)0.0008 (5)0.0065 (6)0.0043 (5)
O10.0702 (8)0.0258 (6)0.0603 (8)0.0037 (5)0.0152 (6)0.0042 (5)
Cl10.0524 (3)0.0506 (3)0.0547 (3)0.0111 (2)0.0019 (2)0.01349 (19)
Cl20.0654 (3)0.0488 (3)0.0479 (3)0.0055 (2)0.0006 (2)0.01029 (19)
Geometric parameters (Å, º) top
C1—O11.2257 (19)C8—C131.387 (2)
C1—N11.352 (2)C8—C91.391 (2)
C1—C21.493 (2)C8—N11.411 (2)
C2—C71.388 (2)C9—C101.381 (2)
C2—C31.393 (2)C9—Cl11.7337 (16)
C3—C41.380 (2)C10—C111.373 (3)
C3—H3A0.9300C10—H10A0.9300
C4—C51.386 (2)C11—C121.390 (3)
C4—Cl21.7404 (16)C11—H11A0.9300
C5—C61.379 (3)C12—C131.378 (3)
C5—H5A0.9300C12—H12A0.9300
C6—C71.380 (3)C13—H13A0.9300
C6—H6A0.9300N1—H1A0.8600
C7—H7A0.9300
O1—C1—N1123.23 (15)C13—C8—C9117.77 (15)
O1—C1—C2120.84 (15)C13—C8—N1122.54 (15)
N1—C1—C2115.93 (13)C9—C8—N1119.69 (14)
C7—C2—C3119.73 (15)C10—C9—C8121.52 (15)
C7—C2—C1117.73 (14)C10—C9—Cl1118.63 (13)
C3—C2—C1122.53 (14)C8—C9—Cl1119.84 (12)
C4—C3—C2118.95 (15)C11—C10—C9119.68 (17)
C4—C3—H3A120.5C11—C10—H10A120.2
C2—C3—H3A120.5C9—C10—H10A120.2
C3—C4—C5121.70 (15)C10—C11—C12120.00 (17)
C3—C4—Cl2119.88 (13)C10—C11—H11A120.0
C5—C4—Cl2118.41 (13)C12—C11—H11A120.0
C6—C5—C4118.66 (16)C13—C12—C11119.71 (17)
C6—C5—H5A120.7C13—C12—H12A120.1
C4—C5—H5A120.7C11—C12—H12A120.1
C5—C6—C7120.75 (16)C12—C13—C8121.31 (17)
C5—C6—H6A119.6C12—C13—H13A119.3
C7—C6—H6A119.6C8—C13—H13A119.3
C6—C7—C2120.17 (16)C1—N1—C8125.58 (13)
C6—C7—H7A119.9C1—N1—H1A117.2
C2—C7—H7A119.9C8—N1—H1A117.2
O1—C1—C2—C734.2 (2)N1—C8—C9—C10178.97 (16)
N1—C1—C2—C7145.40 (15)C13—C8—C9—Cl1179.20 (13)
O1—C1—C2—C3144.21 (17)N1—C8—C9—Cl11.8 (2)
N1—C1—C2—C336.2 (2)C8—C9—C10—C110.5 (3)
C7—C2—C3—C40.4 (2)Cl1—C9—C10—C11178.75 (15)
C1—C2—C3—C4178.75 (14)C9—C10—C11—C120.6 (3)
C2—C3—C4—C51.3 (2)C10—C11—C12—C130.2 (3)
C2—C3—C4—Cl2178.43 (11)C11—C12—C13—C80.3 (3)
C3—C4—C5—C61.5 (3)C9—C8—C13—C120.4 (3)
Cl2—C4—C5—C6178.26 (14)N1—C8—C13—C12179.35 (16)
C4—C5—C6—C70.0 (3)O1—C1—N1—C82.0 (3)
C5—C6—C7—C21.7 (3)C2—C1—N1—C8178.39 (14)
C3—C2—C7—C61.8 (2)C13—C8—N1—C137.2 (2)
C1—C2—C7—C6179.71 (15)C9—C8—N1—C1143.89 (16)
C13—C8—C9—C100.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.142.9157 (17)151
Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC13H9Cl2NO
Mr266.11
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)11.1371 (4), 4.85230 (17), 21.5198 (8)
β (°) 90.142 (3)
V3)1162.94 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.54
Crystal size (mm)0.66 × 0.30 × 0.08
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby Gemini
diffractometer
Absorption correctionAnalytical
[CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]
Tmin, Tmax0.824, 0.958
No. of measured, independent and
observed [I > 2σ(I)] reflections
22845, 3262, 2279
Rint0.034
(sin θ/λ)max1)0.694
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.118, 1.07
No. of reflections3262
No. of parameters154
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.26

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2002), enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.142.9157 (17)150.7
Symmetry code: (i) x, y+1, z.
 

Acknowledgements

PH and JK thank the VEGA Grant Agency of the Slovak Ministry of Education (1/0679/11) and the Research and Development Agency of Slovakia (APVV-0202–10) for support, and the Structural Funds, Inter­reg IIIA, for financial support in purchasing the diffractometer. VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS research fellowship.

References

First citationAllen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338.  Web of Science CrossRef CAS IUCr Journals
First citationBowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1–o3.  Web of Science CSD CrossRef CAS IUCr Journals
First citationBrandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationClark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887–897.  CrossRef CAS Web of Science IUCr Journals
First citationGowda, B. T., Dou, S. & Weiss, A. (1996). Z. Naturforsch. Teil A, 51, 627–636.  CAS
First citationGowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o949.  Web of Science CSD CrossRef IUCr Journals
First citationGowda, B. T., Paulus, H. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 791–800.  CAS
First citationJayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491–500.  CAS
First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
First citationSaeed, A., Arshad, M. & Simpson, J. (2010). Acta Cryst. E66, o2808–o2809.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationShetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113–120.  CAS

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds