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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 12| December 2011| Page o3329
https://doi.org/10.1107/S1600536811047805

3-Chloro-N-phenyl­benzamide

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 3 November 2011; accepted 10 November 2011; online 16 November 2011)

In the title compound, C13H10ClNO, the meta-chloro group on the benzoyl ring is positioned syn to the C=O bond. The two aromatic rings make a dihedral angle of 88.5 (3)°. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into C(4) chains propagating in [010].

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 our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bhat & Gowda (2000[Bhat, D. K. & Gowda, B. T. (2000). J. Indian Chem. Soc. 77, 279-284.]); 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. (2008[Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o949.]); 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, o2339.]), 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-amides, see: Gowda & Weiss (1994[Gowda, B. T. & Weiss, A. (1994). Z. Naturforsch. Teil A, 49, 695-702.]).

[Scheme 1]

Experimental

Crystal data

  • C13H10ClNO

  • Mr = 231.67

  • Monoclinic, P 21 /c

  • a = 25.0232 (9) Å

  • b = 5.3705 (2) Å

  • c = 8.1289 (3) Å

  • β = 98.537 (3)°

  • V = 1080.32 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.33 mm−1

  • T = 293 K

  • 0.90 × 0.79 × 0.05 mm
Data collection

  • Oxford 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 = 0.752, Tmax = 0.984

  • 18170 measured reflections

  • 3020 independent reflections

  • 2270 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.124

  • S = 1.03

  • 3020 reflections

  • 145 parameters

  • H-atom parameters constrained

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.34 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 2.40 3.2377 (17) 165
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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811047805/ds2154sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047805/ds2154Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811047805/ds2154Isup3.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 (Bhat & Gowda, 2000; Bowes et al., 2003; Gowda et al., 2008; Saeed et al., 2010, N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005) and N-chloro-arylamides (Gowda & Weiss, 1994), in the present work, the crystal structure of 3-Chloro-N-(phenyl)benzamide (I) has been determined (Fig.1).

In (I), the meta-chloro group in the benzoyl ring is positioned syn to the C=O bond, while the N—H and C=O bonds in the C—NH—C(O)—C segment are anti to each other, similar to that observed in 3-Chloro-N-(3-chlorophenyl)-benzamide (II) (Gowda et al., 2008). Further, the two aromatic rings in (I) make the dihedral angle of 88.5 (3)°.

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 our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bhat & Gowda (2000); Bowes et al. (2003); Gowda et al. (2008); 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-amides, see: Gowda & Weiss (1994).

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 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).

Structure description 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 (Bhat & Gowda, 2000; Bowes et al., 2003; Gowda et al., 2008; Saeed et al., 2010, N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005) and N-chloro-arylamides (Gowda & Weiss, 1994), in the present work, the crystal structure of 3-Chloro-N-(phenyl)benzamide (I) has been determined (Fig.1).

In (I), the meta-chloro group in the benzoyl ring is positioned syn to the C=O bond, while the N—H and C=O bonds in the C—NH—C(O)—C segment are anti to each other, similar to that observed in 3-Chloro-N-(3-chlorophenyl)-benzamide (II) (Gowda et al., 2008). Further, the two aromatic rings in (I) make the dihedral angle of 88.5 (3)°.

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.

For the preparation of the title compound, see: Gowda et al. (2003). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bhat & Gowda (2000); Bowes et al. (2003); Gowda et al. (2008); 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-amides, see: Gowda & Weiss (1994).

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-phenylbenzamide top
Crystal data top
C13H10ClNOF(000) = 480
Mr = 231.67Dx = 1.424 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6202 reflections
a = 25.0232 (9) Åθ = 3.8–29.5°
b = 5.3705 (2) ŵ = 0.33 mm−1
c = 8.1289 (3) ÅT = 293 K
β = 98.537 (3)°Rod, colorless
V = 1080.32 (7) Å30.90 × 0.79 × 0.05 mm
Z = 4
Data collection top
Oxford Xcalibur Ruby Gemini
diffractometer		3020 independent reflections
Radiation source: Enhance (Mo) X-ray Source2270 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 10.4340 pixels mm-1θmax = 29.5°, θmin = 3.8°
ω scansh = −34→34
Absorption correction: analytical
[CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]		k = −7→7
Tmin = 0.752, Tmax = 0.984l = −11→11
18170 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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.063P)2 + 0.3141P]
where P = (Fo2 + 2Fc2)/3
3020 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.48 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
Crystal data top
C13H10ClNOV = 1080.32 (7) Å3
Mr = 231.67Z = 4
Monoclinic, P21/cMo Kα radiation
a = 25.0232 (9) ŵ = 0.33 mm−1
b = 5.3705 (2) ÅT = 293 K
c = 8.1289 (3) Å0.90 × 0.79 × 0.05 mm
β = 98.537 (3)°
Data collection top
Oxford Xcalibur Ruby Gemini
diffractometer		3020 independent reflections
Absorption correction: analytical
[CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]		2270 reflections with I > 2σ(I)
Tmin = 0.752, Tmax = 0.984Rint = 0.024
18170 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 1.03Δρmax = 0.48 e Å−3
3020 reflectionsΔρmin = −0.34 e Å−3
145 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
C10.24828 (6)0.1506 (3)0.40582 (19)0.0408 (3)
C20.19382 (5)0.0662 (3)0.44101 (18)0.0387 (3)
C30.14947 (6)0.2149 (3)0.38313 (19)0.0408 (3)
H3A0.15390.36240.32680.049*
C40.09844 (6)0.1399 (3)0.41060 (19)0.0421 (3)
C50.09099 (6)−0.0774 (3)0.4947 (2)0.0474 (4)
H5A0.0565−0.12660.51090.057*
C60.13523 (7)−0.2200 (3)0.5540 (2)0.0505 (4)
H6A0.1306−0.36500.61290.061*
C70.18657 (6)−0.1510 (3)0.5275 (2)0.0451 (3)
H7A0.2161−0.25000.56750.054*
C80.33745 (5)−0.0128 (3)0.35872 (18)0.0374 (3)
C90.35764 (6)−0.1981 (3)0.2665 (2)0.0445 (3)
H9A0.3354−0.32830.22310.053*
C100.41083 (7)−0.1893 (3)0.2391 (2)0.0511 (4)
H10A0.4242−0.31340.17670.061*
C110.44399 (6)0.0017 (3)0.3037 (2)0.0505 (4)
H11A0.47980.00690.28530.061*
C120.42390 (6)0.1857 (3)0.3960 (2)0.0497 (4)
H12A0.44640.31470.44000.060*
C130.37059 (6)0.1805 (3)0.4241 (2)0.0451 (4)
H13A0.35730.30530.48620.054*
Cl10.042556 (15)0.32323 (9)0.33863 (6)0.06042 (18)
N10.28327 (5)−0.0372 (2)0.38904 (16)0.0421 (3)
H1A0.2714−0.18630.39760.051*
O10.25904 (5)0.3707 (2)0.39138 (18)0.0587 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0323 (7)0.0365 (8)0.0530 (8)0.0019 (5)0.0046 (6)0.0003 (6)
C20.0340 (7)0.0361 (7)0.0465 (7)0.0002 (5)0.0074 (6)−0.0040 (6)
C30.0342 (7)0.0363 (7)0.0528 (8)−0.0005 (5)0.0088 (6)−0.0001 (6)
C40.0328 (7)0.0417 (8)0.0522 (8)−0.0004 (6)0.0079 (6)−0.0051 (6)
C50.0405 (8)0.0457 (9)0.0589 (9)−0.0068 (6)0.0174 (7)−0.0050 (7)
C60.0564 (10)0.0402 (8)0.0584 (10)−0.0030 (7)0.0199 (8)0.0050 (7)
C70.0439 (8)0.0399 (8)0.0521 (8)0.0052 (6)0.0096 (6)0.0025 (6)
C80.0306 (6)0.0353 (7)0.0461 (7)0.0018 (5)0.0047 (5)0.0036 (6)
C90.0384 (8)0.0397 (8)0.0549 (9)0.0003 (6)0.0053 (6)−0.0042 (6)
C100.0427 (8)0.0525 (10)0.0600 (10)0.0074 (7)0.0133 (7)−0.0040 (7)
C110.0342 (7)0.0553 (10)0.0634 (10)0.0011 (7)0.0118 (7)0.0063 (8)
C120.0375 (8)0.0454 (9)0.0650 (10)−0.0074 (6)0.0035 (7)0.0014 (7)
C130.0383 (7)0.0392 (8)0.0573 (9)−0.0003 (6)0.0059 (6)−0.0043 (6)
Cl10.0316 (2)0.0611 (3)0.0886 (4)0.00427 (16)0.00877 (19)0.0092 (2)
N10.0326 (6)0.0342 (6)0.0599 (7)−0.0004 (5)0.0085 (5)−0.0018 (5)
O10.0390 (6)0.0354 (6)0.1034 (10)0.0009 (4)0.0155 (6)0.0043 (6)
Geometric parameters (Å, º) top
C1—O11.2220 (18)C8—C131.384 (2)
C1—N11.3558 (18)C8—C91.385 (2)
C1—C21.5033 (19)C8—N11.4195 (18)
C2—C71.387 (2)C9—C101.382 (2)
C2—C31.391 (2)C9—H9A0.9300
C3—C41.3881 (19)C10—C111.374 (2)
C3—H3A0.9300C10—H10A0.9300
C4—C51.379 (2)C11—C121.380 (2)
C4—Cl11.7390 (15)C11—H11A0.9300
C5—C61.374 (2)C12—C131.387 (2)
C5—H5A0.9300C12—H12A0.9300
C6—C71.384 (2)C13—H13A0.9300
C6—H6A0.9300N1—H1A0.8600
C7—H7A0.9300
O1—C1—N1123.72 (14)C13—C8—C9120.04 (13)
O1—C1—C2121.93 (13)C13—C8—N1122.38 (13)
N1—C1—C2114.34 (12)C9—C8—N1117.51 (13)
C7—C2—C3119.74 (13)C10—C9—C8119.99 (15)
C7—C2—C1122.71 (13)C10—C9—H9A120.0
C3—C2—C1117.55 (13)C8—C9—H9A120.0
C4—C3—C2119.06 (14)C11—C10—C9120.34 (15)
C4—C3—H3A120.5C11—C10—H10A119.8
C2—C3—H3A120.5C9—C10—H10A119.8
C5—C4—C3121.36 (14)C10—C11—C12119.62 (15)
C5—C4—Cl1118.99 (11)C10—C11—H11A120.2
C3—C4—Cl1119.65 (12)C12—C11—H11A120.2
C6—C5—C4118.99 (14)C11—C12—C13120.81 (15)
C6—C5—H5A120.5C11—C12—H12A119.6
C4—C5—H5A120.5C13—C12—H12A119.6
C5—C6—C7120.94 (15)C8—C13—C12119.20 (14)
C5—C6—H6A119.5C8—C13—H13A120.4
C7—C6—H6A119.5C12—C13—H13A120.4
C6—C7—C2119.88 (15)C1—N1—C8126.62 (13)
C6—C7—H7A120.1C1—N1—H1A116.7
C2—C7—H7A120.1C8—N1—H1A116.7
O1—C1—C2—C7−150.79 (16)C1—C2—C7—C6−179.20 (15)
N1—C1—C2—C730.3 (2)C13—C8—C9—C10−0.3 (2)
O1—C1—C2—C329.3 (2)N1—C8—C9—C10−177.28 (14)
N1—C1—C2—C3−149.65 (14)C8—C9—C10—C110.4 (3)
C7—C2—C3—C4−1.2 (2)C9—C10—C11—C12−0.2 (3)
C1—C2—C3—C4178.75 (13)C10—C11—C12—C13−0.1 (3)
C2—C3—C4—C50.4 (2)C9—C8—C13—C120.0 (2)
C2—C3—C4—Cl1−179.84 (11)N1—C8—C13—C12176.84 (14)
C3—C4—C5—C60.9 (2)C11—C12—C13—C80.2 (3)
Cl1—C4—C5—C6−178.89 (13)O1—C1—N1—C82.4 (3)
C4—C5—C6—C7−1.3 (3)C2—C1—N1—C8−178.75 (13)
C5—C6—C7—C20.5 (3)C13—C8—N1—C134.8 (2)
C3—C2—C7—C60.7 (2)C9—C8—N1—C1−148.36 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.403.2377 (17)165
Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formulaC13H10ClNO
Mr231.67
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)25.0232 (9), 5.3705 (2), 8.1289 (3)
β (°) 98.537 (3)
V (Å3)1080.32 (7)
Z4
Radiation typeMo Kα
µ (mm−1)0.33
Crystal size (mm)0.90 × 0.79 × 0.05
Data collection
DiffractometerOxford Xcalibur Ruby Gemini
Absorption correctionAnalytical
[CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]
Tmin, Tmax0.752, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections		18170, 3020, 2270
Rint0.024
(sin θ/λ)max (Å−1)0.692
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.124, 1.03
No. of reflections3020
No. of parameters145
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.48, −0.34

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···O1i0.862.403.2377 (17)165.2
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 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

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3329
https://doi.org/10.1107/S1600536811047805
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