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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 11| November 2011| Page o2940
doi:10.1107/S1600536811041651

2-Chloro-N-(4-methyl­phen­yl)benzamide

Vinola Z. Rodrigues,a Peter Herich,b B. Thimme Gowdaa* and Jozef Kožíšekb

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 7 October 2011; accepted 10 October 2011; online 12 October 2011)

In the title compound, C14H12ClNO, the ortho-Cl atom in the benzoyl ring is positioned syn to the C=O bond. The benzoyl and aniline benzene rings are tilted relative to each other by 82.8 (1)°. In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into infinite chains running along the c-axis direction.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003[Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225-230.]). For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: 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.]); Gowda et al. (2000[Gowda, B. T., Paulus, H. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 711-720.]); Saeed et al. (2010[Saeed, A., Arshad, M. & Simpson, J. (2010). Acta Cryst. E66, o2808-o2809.]), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2570.]), on N-(ar­yl)-aryl­sulfonamides, see: Shetty & Gowda (2005[Shetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113-120.]) and on N-chloro-aryl­sulfonamides, see: Gowda & Shetty (2004[Gowda, B. T. & Shetty, M. (2004). J. Phys. Org. Chem. 17, 848-864.]).

[Scheme 1]

Experimental

Crystal data

  • C14H12ClNO

  • Mr = 245.70

  • Monoclinic, P 21 /c

  • a = 20.2969 (14) Å

  • b = 7.1850 (5) Å

  • c = 8.8662 (5) Å

  • β = 93.750 (5)°

  • V = 1290.22 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 293 K

  • 0.92 × 0.28 × 0.07 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 from Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.911, Tmax = 0.981

  • 21209 measured reflections

  • 3594 independent reflections

  • 1870 reflections with I > 2σ(I)

  • Rint = 0.038
Refinement

  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.138

  • S = 1.03

  • 3594 reflections

  • 154 parameters

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.42 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O1i 0.86 2.01 2.847 (2) 165
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811041651/bt5668sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041651/bt5668Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811041651/bt5668Isup3.cml

checkCIF report


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 (Bowes et al., 2003; Gowda et al., 2000; Saeed et al., 2010), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005) and N-chloro-arylsulfonamides (Gowda & Shetty, 2004), in the present work, the crystal structure of 2-chloro-N-(4-methylphenyl)benzamide (I) has been determined (Fig.1).

In (I), the ortho-Cl atom in the benzoyl ring is positioned syn to the C=O bond and anti to the N–H bond of the C—NH—C(O)—C segment.

The central amide group –NHCO– is tilted to the anilino ring with the C9—C8—N1—C1 and C13—C8—N1—C1 torsion angles of -144.4 (2)° and 35.6 (3)°. The C3—C2—C1—N1 and C7—C2—C1—N1 torsion angles are -118.8 (2)° and 64.0 (3)°, respectively, while the C3—C2—C1—O1 and C7—C2—C1—O1 torsion angles are 61.8 (3)° and -115.4 (2)°, respectively. But the C2—C1—N1—C8 and C8—N1—C1—O1 torsion angles are 178.0 (2)° and -2.7 (3)°, respectively.

In the crystal structure, intermolecular N—H···O hydrogen bonds link the molecules into infinite chains running along the c-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. (2003). For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003); Gowda et al. (2000); Saeed et al. (2010), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007), on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005) and on N-chloro-arylsulfonamides, see: Gowda & Shetty (2004).

Experimental top

The title compound was prepared according to the method described by 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. Rod like colourless 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 30 ml of ethanol) at room temperature.

Refinement top

All hydrogen atoms were placed in calculated positions with C–H distances of 0.93Å (C-aromatic), 0.96Å (C-methyl), 0.86Å (N-H) and constrained to ride on their parent atoms. The Uiso(H) values were set at 1.2 Ueq (C-aromatic, N) and 1.5 Ueq(C-methyl).

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. H atoms not involved in intermolecular bonding have been omitted.
2-Chloro-N-(4-methylphenyl)benzamide top
Crystal data top
C14H12ClNOF(000) = 512
Mr = 245.70Dx = 1.265 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3776 reflections
a = 20.2969 (14) Åθ = 3.5–29.5°
b = 7.1850 (5) ŵ = 0.28 mm−1
c = 8.8662 (5) ÅT = 293 K
β = 93.750 (5)°Rod, colorless
V = 1290.22 (15) Å30.92 × 0.28 × 0.07 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		3594 independent reflections
Radiation source: Enhance (Mo) X-ray Source1870 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
Detector resolution: 10.4340 pixels mm-1θmax = 29.5°, θmin = 3.5°
ω scansh = −28→28
Absorption correction: analytical
[CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)]		k = −9→9
Tmin = 0.911, Tmax = 0.981l = −12→12
21209 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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0457P)2 + 0.4284P]
where P = (Fo2 + 2Fc2)/3
3594 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.35 e Å−3
0 restraintsΔρmin = −0.42 e Å−3
Crystal data top
C14H12ClNOV = 1290.22 (15) Å3
Mr = 245.70Z = 4
Monoclinic, P21/cMo Kα radiation
a = 20.2969 (14) ŵ = 0.28 mm−1
b = 7.1850 (5) ÅT = 293 K
c = 8.8662 (5) Å0.92 × 0.28 × 0.07 mm
β = 93.750 (5)°
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		3594 independent reflections
Absorption correction: analytical
[CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)]		1870 reflections with I > 2σ(I)
Tmin = 0.911, Tmax = 0.981Rint = 0.038
21209 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.138H-atom parameters constrained
S = 1.03Δρmax = 0.35 e Å−3
3594 reflectionsΔρmin = −0.42 e Å−3
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
C10.22887 (10)0.1405 (3)0.4095 (2)0.0490 (5)
C20.17841 (10)0.0438 (3)0.30648 (19)0.0481 (5)
C30.11200 (11)0.0438 (3)0.3330 (2)0.0568 (5)
C40.06674 (12)−0.0529 (4)0.2409 (3)0.0719 (6)
H4A0.0221−0.05000.25890.086*
C50.08826 (14)−0.1534 (4)0.1225 (3)0.0820 (8)
H5A0.0581−0.22150.06140.098*
C60.15356 (14)−0.1548 (4)0.0931 (3)0.0808 (8)
H6A0.1675−0.22270.01180.097*
C70.19841 (11)−0.0560 (3)0.1836 (2)0.0616 (6)
H7A0.2427−0.05590.16240.074*
C80.31056 (9)0.3950 (3)0.4145 (2)0.0524 (5)
C90.31260 (12)0.5767 (4)0.3668 (3)0.0693 (6)
H9A0.28260.61780.29010.083*
C100.35880 (13)0.6989 (4)0.4316 (3)0.0797 (7)
H10A0.35900.82180.39870.096*
C110.40448 (12)0.6430 (4)0.5435 (3)0.0757 (7)
C120.40141 (11)0.4610 (5)0.5898 (3)0.0802 (8)
H12A0.43150.42010.66640.096*
C130.35533 (11)0.3354 (4)0.5273 (2)0.0668 (6)
H13A0.35480.21300.56120.080*
C140.45614 (15)0.7752 (5)0.6112 (3)0.1150 (12)
H14C0.48330.71170.68760.138*
H14B0.43490.87910.65560.138*
H14A0.48310.81870.53350.138*
N10.26167 (8)0.2768 (2)0.34391 (17)0.0544 (4)
H1A0.25210.29470.24910.065*
O10.23840 (8)0.0938 (2)0.54154 (14)0.0692 (5)
Cl10.08462 (3)0.17186 (12)0.48200 (8)0.0953 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0552 (11)0.0531 (12)0.0382 (10)0.0015 (10)−0.0008 (8)−0.0014 (9)
C20.0600 (12)0.0441 (11)0.0395 (10)−0.0023 (9)−0.0016 (8)0.0020 (9)
C30.0613 (13)0.0547 (13)0.0540 (11)0.0004 (10)0.0018 (10)−0.0008 (10)
C40.0613 (14)0.0739 (16)0.0796 (16)−0.0134 (12)−0.0017 (12)−0.0015 (14)
C50.0859 (19)0.0788 (18)0.0796 (17)−0.0274 (15)−0.0074 (14)−0.0225 (14)
C60.096 (2)0.0765 (18)0.0701 (15)−0.0153 (15)0.0047 (14)−0.0292 (14)
C70.0690 (14)0.0618 (14)0.0541 (12)−0.0077 (11)0.0048 (10)−0.0105 (11)
C80.0491 (11)0.0684 (15)0.0396 (10)−0.0058 (10)0.0023 (8)−0.0047 (10)
C90.0732 (15)0.0747 (17)0.0586 (13)−0.0149 (13)−0.0072 (11)0.0063 (12)
C100.0863 (18)0.0782 (18)0.0751 (16)−0.0268 (15)0.0082 (14)−0.0070 (14)
C110.0594 (14)0.104 (2)0.0648 (15)−0.0233 (14)0.0090 (12)−0.0228 (15)
C120.0530 (14)0.116 (2)0.0688 (15)0.0004 (15)−0.0146 (11)−0.0135 (16)
C130.0573 (13)0.0780 (16)0.0631 (13)0.0035 (12)−0.0111 (11)−0.0031 (12)
C140.085 (2)0.156 (3)0.105 (2)−0.051 (2)0.0105 (17)−0.046 (2)
N10.0606 (10)0.0670 (11)0.0341 (8)−0.0105 (9)−0.0069 (7)0.0021 (8)
O10.0919 (11)0.0781 (11)0.0360 (7)−0.0142 (9)−0.0084 (7)0.0082 (7)
Cl10.0758 (5)0.1171 (6)0.0947 (5)0.0072 (4)0.0185 (4)−0.0381 (4)
Geometric parameters (Å, º) top
C1—O11.221 (2)C8—C131.375 (3)
C1—N11.339 (2)C8—N11.420 (2)
C1—C21.498 (3)C9—C101.382 (3)
C2—C31.383 (3)C9—H9A0.9300
C2—C71.387 (3)C10—C111.373 (4)
C3—C41.377 (3)C10—H10A0.9300
C3—Cl11.731 (2)C11—C121.373 (4)
C4—C51.369 (3)C11—C141.510 (3)
C4—H4A0.9300C12—C131.389 (3)
C5—C61.368 (4)C12—H12A0.9300
C5—H5A0.9300C13—H13A0.9300
C6—C71.372 (3)C14—H14C0.9600
C6—H6A0.9300C14—H14B0.9600
C7—H7A0.9300C14—H14A0.9600
C8—C91.374 (3)N1—H1A0.8600
O1—C1—N1124.43 (18)C8—C9—C10120.6 (2)
O1—C1—C2121.11 (18)C8—C9—H9A119.7
N1—C1—C2114.45 (15)C10—C9—H9A119.7
C3—C2—C7118.16 (18)C11—C10—C9121.5 (3)
C3—C2—C1122.10 (17)C11—C10—H10A119.3
C7—C2—C1119.68 (18)C9—C10—H10A119.3
C4—C3—C2121.3 (2)C10—C11—C12116.9 (2)
C4—C3—Cl1119.06 (18)C10—C11—C14121.5 (3)
C2—C3—Cl1119.65 (16)C12—C11—C14121.6 (3)
C5—C4—C3119.1 (2)C11—C12—C13122.8 (2)
C5—C4—H4A120.4C11—C12—H12A118.6
C3—C4—H4A120.4C13—C12—H12A118.6
C6—C5—C4120.8 (2)C8—C13—C12118.9 (3)
C6—C5—H5A119.6C8—C13—H13A120.5
C4—C5—H5A119.6C12—C13—H13A120.5
C5—C6—C7119.9 (2)C11—C14—H14C109.5
C5—C6—H6A120.0C11—C14—H14B109.5
C7—C6—H6A120.0H14C—C14—H14B109.5
C6—C7—C2120.7 (2)C11—C14—H14A109.5
C6—C7—H7A119.7H14C—C14—H14A109.5
C2—C7—H7A119.7H14B—C14—H14A109.5
C9—C8—C13119.2 (2)C1—N1—C8126.81 (15)
C9—C8—N1117.82 (18)C1—N1—H1A116.6
C13—C8—N1122.9 (2)C8—N1—H1A116.6
O1—C1—C2—C361.8 (3)C13—C8—C9—C10−0.4 (3)
N1—C1—C2—C3−118.8 (2)N1—C8—C9—C10179.6 (2)
O1—C1—C2—C7−115.4 (2)C8—C9—C10—C110.9 (4)
N1—C1—C2—C763.9 (2)C9—C10—C11—C12−1.1 (4)
C7—C2—C3—C40.3 (3)C9—C10—C11—C14178.3 (3)
C1—C2—C3—C4−177.0 (2)C10—C11—C12—C130.8 (4)
C7—C2—C3—Cl1−178.22 (16)C14—C11—C12—C13−178.6 (2)
C1—C2—C3—Cl14.5 (3)C9—C8—C13—C120.0 (3)
C2—C3—C4—C51.1 (4)N1—C8—C13—C12−180.0 (2)
Cl1—C3—C4—C5179.6 (2)C11—C12—C13—C8−0.2 (4)
C3—C4—C5—C6−1.6 (4)O1—C1—N1—C8−2.7 (3)
C4—C5—C6—C70.6 (4)C2—C1—N1—C8178.00 (18)
C5—C6—C7—C20.9 (4)C9—C8—N1—C1−144.4 (2)
C3—C2—C7—C6−1.3 (3)C13—C8—N1—C135.6 (3)
C1—C2—C7—C6176.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.012.847 (2)165
Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC14H12ClNO
Mr245.70
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)20.2969 (14), 7.1850 (5), 8.8662 (5)
β (°) 93.750 (5)
V (Å3)1290.22 (15)
Z4
Radiation typeMo Kα
µ (mm−1)0.28
Crystal size (mm)0.92 × 0.28 × 0.07
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby Gemini
diffractometer
Absorption correctionAnalytical
[CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)]
Tmin, Tmax0.911, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections		21209, 3594, 1870
Rint0.038
(sin θ/λ)max (Å−1)0.693
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.138, 1.03
No. of reflections3594
No. of parameters154
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.35, −0.42

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···O1i0.862.012.847 (2)164.5
Symmetry code: (i) x, −y+1/2, z−1/2.
 

Acknowledgements

PH and JK thank the VEGA Grant Agency of Slovak Ministry of Education 1/0679/11 and the Research and Development Agency of Slovakia (APVV-0202–10) for financial 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 Google Scholar
 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 Google Scholar
 First citationBrandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
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ISSN: 2056-9890
Volume 67| Part 11| November 2011| Page o2940
doi:10.1107/S1600536811041651
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