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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890

N-(4-Chloro­phen­yl)benzamide

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, bFaculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and cInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, Darmstadt, D-64287, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 20 March 2008; accepted 26 March 2008; online 29 March 2008)

The structure of the title compound, C13H10ClNO, resembles those of N-phen­ylbenzamide, N-(2-chloro­phenyl)­benzamide and other benzanilides, with similar bond parameters. The amide group –NHCO– makes a dihedral angle of 29.95 (9)° with the benzoyl ring, while the benzoyl and aniline rings form a dihedral angle of 60.76 (3)°. The structure shows both intra- and inter­molecular hydrogen bonding. The mol­ecules are linked by N—H⋯O hydrogen bonds into chains running along the [100] direction.

Related literature

For related literature, see: Gowda et al. (2003[Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225-230.], 2007[Gowda, B. T., Sowmya, B. P., Kožíšek, J., Tokarčík, M. & Fuess, H. (2007). Acta Cryst. E63, o2906.], 2008[Gowda, B. T., Tokarčík, M., Kožíšek, J. & Sowmya, B. P. (2008). Acta Cryst. E64, o83.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10ClNO

  • Mr = 231.67

  • Triclinic, [P \overline 1]

  • a = 5.3789 (1) Å

  • b = 7.8501 (2) Å

  • c = 13.6318 (4) Å

  • α = 106.509 (2)°

  • β = 98.380 (2)°

  • γ = 90.631 (2)°

  • V = 545.15 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.33 mm−1

  • T = 295 (2) K

  • 0.52 × 0.25 × 0.08 mm

Data collection
  • Oxford Xcalibur diffractometer

  • Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]), using a multifaceted crystal model based on expressions derived by Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.852, Tmax = 0.975

  • 23656 measured reflections

  • 2087 independent reflections

  • 1773 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.091

  • S = 1.08

  • 2087 reflections

  • 148 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C9—H9⋯O1 0.93 2.43 2.9090 (17) 112
N1—H1N⋯O1i 0.845 (16) 2.390 (16) 3.1710 (15) 154.0 (15)
C13—H13⋯O1i 0.93 2.58 3.2507 (11) 129
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); data reduction: CrysAlis RED; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2002[Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]) and WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

In the present work, the structure of N-(4-chlorophenyl)benzamide (N4CPBA) has been determined to study the effect of substituents on the structures of benzanilides (Gowda et al., 2003, 2007, 2008).

The structure of N4CPBA (Fig.1) is similar to those of N-(phenyl)benzamide, N-(2-chlorophenyl)benzamide, N-(3-chlorophenyl)benzamide and N-(4-methylphenyl)benzamide and other benzanilides (Gowda et al., 2003, 2007, 2008). The amide group –NHCO– forms dihedral angle of 29.95 (9)° with the benzoyl ring, while the two benzene rings (benzoyl and aniline rings) form dihedral angle of 60.76 (3)°. Part of the structure of N4CPBA as viewed down the b axis and showing infinite molecular chains in the [100] direction is shown in Fig. 2. The chains are generated by the intermolecular N—H···O hydrogen bonds (Table 1).

Related literature top

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

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 attached to C atoms were placed in calculated positions and subsequently treated as riding with C—H distance 0.93 Å. H atom of the amide group was refined with the N—H distance restrained to 0.86 (4) Å. The Uiso(H) values were set at 1.2 Ueq(C,N).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), 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. Intramolecular hydrogen bond C9—H9···O1 is shown by dashed line.
[Figure 2] Fig. 2. Part of the crystal structure of the title compound viewed down the b axis and showing infinite molecular chains in the[100] direction. H atoms not involved in intermolecular bonding have been omitted. [Symmetry code: (i) x + 1, y, z]
N-(4-Chlorophenyl)-benzamide top
Crystal data top
C13H10ClNOZ = 2
Mr = 231.67F(000) = 240
Triclinic, P1Dx = 1.411 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.3789 (1) ÅCell parameters from 13860 reflections
b = 7.8501 (2) Åθ = 3.1–29.3°
c = 13.6318 (4) ŵ = 0.33 mm1
α = 106.509 (2)°T = 295 K
β = 98.380 (2)°Block, colorless
γ = 90.631 (2)°0.52 × 0.25 × 0.08 mm
V = 545.15 (2) Å3
Data collection top
Oxford Xcalibur
diffractometer
2087 independent reflections
Radiation source: fine-focus sealed tube1773 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 10.434 pixels mm-1θmax = 25.8°, θmin = 5.6°
ϕ scans, and ω scans with κ offsetsh = 66
Absorption correction: analytical
[CrysAlis RED (Oxford Diffraction, 2007). Analytical absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]
k = 99
Tmin = 0.852, Tmax = 0.975l = 1616
23656 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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0494P)2 + 0.0939P]
where P = (Fo2 + 2Fc2)/3
2087 reflections(Δ/σ)max = 0.001
148 parametersΔρmax = 0.19 e Å3
1 restraintΔρmin = 0.23 e Å3
Crystal data top
C13H10ClNOγ = 90.631 (2)°
Mr = 231.67V = 545.15 (2) Å3
Triclinic, P1Z = 2
a = 5.3789 (1) ÅMo Kα radiation
b = 7.8501 (2) ŵ = 0.33 mm1
c = 13.6318 (4) ÅT = 295 K
α = 106.509 (2)°0.52 × 0.25 × 0.08 mm
β = 98.380 (2)°
Data collection top
Oxford Xcalibur
diffractometer
2087 independent reflections
Absorption correction: analytical
[CrysAlis RED (Oxford Diffraction, 2007). Analytical absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]
1773 reflections with I > 2σ(I)
Tmin = 0.852, Tmax = 0.975Rint = 0.026
23656 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0321 restraint
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.19 e Å3
2087 reflectionsΔρmin = 0.23 e Å3
148 parameters
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
N10.3126 (2)0.77177 (16)0.02982 (9)0.0381 (3)
H1N0.443 (3)0.757 (2)0.0010 (13)0.046*
O10.11350 (19)0.74813 (17)0.00041 (8)0.0563 (3)
C10.0870 (2)0.71549 (18)0.03078 (10)0.0370 (3)
C20.0976 (2)0.61312 (17)0.14032 (10)0.0343 (3)
C30.1018 (2)0.62387 (19)0.21496 (11)0.0396 (3)
H30.23460.69410.19560.047*
C40.1045 (3)0.5314 (2)0.31747 (11)0.0450 (3)
H40.23760.54090.36710.054*
C50.0893 (3)0.4249 (2)0.34662 (11)0.0460 (4)
H50.08710.36210.41580.055*
C60.2867 (3)0.41171 (19)0.27281 (12)0.0452 (3)
H60.41670.33870.29240.054*
C70.2930 (3)0.50593 (18)0.17026 (11)0.0392 (3)
H70.42810.49770.12110.047*
C80.3531 (2)0.87653 (17)0.13439 (10)0.0337 (3)
C90.1943 (3)0.86476 (19)0.20396 (10)0.0396 (3)
H90.05090.78840.18180.048*
C100.2490 (3)0.96646 (19)0.30619 (11)0.0415 (3)
H100.14260.95880.3530.05*
C110.4617 (3)1.07920 (18)0.33843 (10)0.0396 (3)
C120.6211 (3)1.09201 (19)0.27047 (11)0.0419 (3)
H120.76431.16850.2930.05*
C130.56679 (8)0.99040 (5)0.16848 (3)0.0391 (3)
H130.67440.99830.12220.047*
Cl10.53006 (8)1.20876 (5)0.46690 (3)0.06227 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0320 (6)0.0455 (7)0.0326 (6)0.0003 (5)0.0068 (5)0.0037 (5)
O10.0336 (5)0.0849 (8)0.0394 (6)0.0060 (5)0.0073 (4)0.0005 (5)
C10.0337 (7)0.0404 (7)0.0347 (7)0.0024 (5)0.0045 (5)0.0076 (6)
C20.0328 (7)0.0340 (7)0.0345 (7)0.0022 (5)0.0060 (5)0.0069 (5)
C30.0328 (7)0.0422 (7)0.0400 (7)0.0032 (5)0.0043 (5)0.0066 (6)
C40.0402 (8)0.0505 (8)0.0379 (7)0.0029 (6)0.0035 (6)0.0075 (6)
C50.0487 (8)0.0474 (8)0.0342 (7)0.0054 (6)0.0074 (6)0.0009 (6)
C60.0394 (8)0.0436 (8)0.0471 (8)0.0043 (6)0.0117 (6)0.0020 (6)
C70.0335 (7)0.0412 (7)0.0394 (7)0.0023 (5)0.0026 (5)0.0077 (6)
C80.0325 (6)0.0343 (7)0.0323 (6)0.0043 (5)0.0039 (5)0.0067 (5)
C90.0343 (7)0.0451 (8)0.0369 (7)0.0042 (6)0.0026 (5)0.0097 (6)
C100.0404 (7)0.0510 (8)0.0333 (7)0.0031 (6)0.0084 (6)0.0113 (6)
C110.0442 (8)0.0378 (7)0.0317 (7)0.0065 (6)0.0004 (6)0.0043 (5)
C120.0369 (7)0.0385 (7)0.0441 (8)0.0035 (6)0.0005 (6)0.0051 (6)
C130.0347 (7)0.0416 (7)0.0401 (7)0.0007 (5)0.0091 (6)0.0089 (6)
Cl10.0764 (3)0.0615 (3)0.0352 (2)0.0009 (2)0.00138 (18)0.00280 (18)
Geometric parameters (Å, º) top
N1—C11.3560 (18)C6—H60.93
N1—C81.4125 (17)C7—H70.93
N1—H1N0.845 (16)C8—C131.3862 (13)
O1—C11.2196 (16)C8—C91.3862 (18)
C1—C21.4909 (18)C9—C101.3817 (19)
C2—C31.3876 (19)C9—H90.93
C2—C71.3885 (19)C10—C111.377 (2)
C3—C41.377 (2)C10—H100.93
C3—H30.93C11—C121.373 (2)
C4—C51.376 (2)C11—Cl11.7402 (14)
C4—H40.93C12—C131.3786 (15)
C5—C61.379 (2)C12—H120.93
C5—H50.93C13—H130.93
C6—C71.379 (2)
C1—N1—C8126.64 (11)C6—C7—C2120.02 (13)
C1—N1—H1N117.7 (11)C6—C7—H7120
C8—N1—H1N115.0 (12)C2—C7—H7120
O1—C1—N1123.02 (12)C13—C8—C9119.42 (11)
O1—C1—C2121.31 (12)C13—C8—N1117.74 (10)
N1—C1—C2115.66 (11)C9—C8—N1122.80 (12)
C3—C2—C7119.04 (12)C10—C9—C8120.05 (12)
C3—C2—C1117.62 (11)C10—C9—H9120
C7—C2—C1123.33 (12)C8—C9—H9120
C4—C3—C2120.51 (12)C11—C10—C9119.65 (12)
C4—C3—H3119.7C11—C10—H10120.2
C2—C3—H3119.7C9—C10—H10120.2
C5—C4—C3120.17 (13)C12—C11—C10120.97 (13)
C5—C4—H4119.9C12—C11—Cl1119.21 (11)
C3—C4—H4119.9C10—C11—Cl1119.82 (11)
C4—C5—C6119.71 (13)C11—C12—C13119.40 (12)
C4—C5—H5120.1C11—C12—H12120.3
C6—C5—H5120.1C13—C12—H12120.3
C7—C6—C5120.53 (13)C12—C13—C8120.52 (9)
C7—C6—H6119.7C12—C13—H13119.7
C5—C6—H6119.7C8—C13—H13119.7
C8—N1—C1—O11.4 (2)C1—C2—C7—C6178.39 (12)
C8—N1—C1—C2177.27 (12)C1—N1—C8—C13149.06 (12)
O1—C1—C2—C328.33 (19)C1—N1—C8—C933.4 (2)
N1—C1—C2—C3150.35 (12)C13—C8—C9—C100.24 (18)
O1—C1—C2—C7150.27 (14)N1—C8—C9—C10177.75 (12)
N1—C1—C2—C731.06 (18)C8—C9—C10—C110.0 (2)
C7—C2—C3—C40.8 (2)C9—C10—C11—C120.1 (2)
C1—C2—C3—C4179.47 (12)C9—C10—C11—Cl1179.53 (10)
C2—C3—C4—C51.0 (2)C10—C11—C12—C130.0 (2)
C3—C4—C5—C60.3 (2)Cl1—C11—C12—C13179.61 (9)
C4—C5—C6—C70.7 (2)C11—C12—C13—C80.18 (17)
C5—C6—C7—C21.0 (2)C9—C8—C13—C120.32 (15)
C3—C2—C7—C60.2 (2)N1—C8—C13—C12177.95 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O10.932.432.9090 (17)112
N1—H1N···O1i0.85 (2)2.39 (2)3.1710 (15)154 (2)
C13—H13···O1i0.932.583.2507 (11)129
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC13H10ClNO
Mr231.67
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)5.3789 (1), 7.8501 (2), 13.6318 (4)
α, β, γ (°)106.509 (2), 98.380 (2), 90.631 (2)
V3)545.15 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.33
Crystal size (mm)0.52 × 0.25 × 0.08
Data collection
DiffractometerOxford Xcalibur
diffractometer
Absorption correctionAnalytical
[CrysAlis RED (Oxford Diffraction, 2007). Analytical absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]
Tmin, Tmax0.852, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections
23656, 2087, 1773
Rint0.026
(sin θ/λ)max1)0.613
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.091, 1.08
No. of reflections2087
No. of parameters148
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.23

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O10.932.432.9090 (17)111.9
N1—H1N···O1i0.845 (16)2.390 (16)3.1710 (15)154.0 (15)
C13—H13···O1i0.932.583.2507 (11)129.3
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

MT and JK thank the Grant Agency of the Slovak Republic (grant No. VEGA 1/0817/08) and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

References

First citationBrandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationClark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887–897.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationGowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230.  CAS Google Scholar
First citationGowda, B. T., Sowmya, B. P., Kožíšek, J., Tokarčík, M. & Fuess, H. (2007). Acta Cryst. E63, o2906.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGowda, B. T., Tokarčík, M., Kožíšek, J. & Sowmya, B. P. (2008). Acta Cryst. E64, o83.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationOxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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