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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 66| Part 12| December 2010| Page o3338
https://doi.org/10.1107/S160053681004897X

Methyl 2-(4-chloro­benzamido)­benzoate

Islam Ullah Khan,a* Onur Şahin,b Rashid Javaid,a Shahzad Sharifa and Orhan Büyükgüngörb

aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan, and bDepartment of Physics, Ondokuz Mayıs University, TR-55139 Samsun, Turkey
*Correspondence e-mail: iukhan@gcu.edu.pk, onurs@omu.edu.tr

(Received 1 November 2010; accepted 23 November 2010; online 27 November 2010)

In the title compound, C15H12ClNO3, the central C—C(O)—N—C amide unit makes dihedral angles of 6.60 (2) and 3.42 (2)°, respectively, with the 4-chloro­benzene and anilino rings. The dihedral angle between the two benzene rings is 3.32 (3)°. Intra­molecular N—H⋯O and C—H⋯O hydrogen bonds form S(6) rings and contribute to the planarity of this portion of the mol­ecule. In the crystal, inter­molecular C—H⋯O hydrogen bonds are observed, which link the mol­ecules into [010] C(7) chains.

Related literature

For the graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For related structures, see: Gowda et al. (2008[Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o1365.]); Zhou & Zheng (2007[Zhou, B. & Zheng, P.-W. (2007). Acta Cryst. E63, o4630.]); Khan et al. (2010[Khan, I. U., Javaid, R., Sharif, S. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1687.]). Benzamide derivatives are frequently used in the synthesis of new and effective anti-convulsant agents, see: Clark et al. (1988[Clark, C. R. (1988). Epilepsia, 29, 198-203.]); Leander et al. (1988[Leander, J. D., Robertson, D. W., Clark, C. R., Lawson, R. R. & Rathbun, R. C. (1988). Epilepsia, 29, 83-90.]); Diouf et al. (1997[Diouf, O., Bourhim, M., Lambert, D. M., Poupaert, J. H., Stables, J. P. & Vamecq, J. (1997). Biomed. Pharmacother. 51, 131-136.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C15H12ClNO3

  • Mr = 289.71

  • Orthorhombic, P b c a

  • a = 7.3788 (9) Å

  • b = 16.757 (2) Å

  • c = 21.530 (2) Å

  • V = 2662.0 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.29 mm−1

  • T = 296 K

  • 0.21 × 0.12 × 0.08 mm
Data collection

  • Bruker SMART APEXII diffractometer

  • 11139 measured reflections

  • 2399 independent reflections

  • 814 reflections with I > 2σ(I)

  • Rint = 0.166
Refinement

  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.134

  • S = 0.97

  • 2399 reflections

  • 182 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2⋯O1 0.93 2.21 2.839 (6) 124
N1—H1⋯O2 0.86 1.94 2.646 (5) 138
C3—H3⋯O2i 0.93 2.58 3.422 (6) 151
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681004897X/om2376sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004897X/om2376Isup2.hkl

checkCIF report


Comment top

Benzamide derivatives are frequently used in the synthesis of new and effective anti-convulsant agents (Clark et al., 1988; Leander et al., 1988; Diouf et al., 1997). In continuation of our ongoing structural studies of benzamide derivatives (Khan et al., 2010), herein the crystal structure of title compound is described.

In the title compound, Fig. 1, the C1—N1—C9(O1)—C10 amide unit is planar, r.m.s. deviation 0.0102 Å, and subtends dihedral angles of 3.42 (2)° and 6.60 (2)° respectively to the C1···C6 and C10···C15 rings. The two aromatic rings are inclined at 3.32 (3)°. Bond distances within the molecule are normal (Allen et al. 1987) and similar to those observed in comparable structures (Gowda et al. 2008; Zhou & Zheng 2007).

The intramolecular C2—H2···O1 and N1—H1···O2 hydrogen bonds produce S(6) rings (Bernstein et al., 1995) (Fig. 1). The C3—H3 group in the molecule at acts as a hydrogen-bond donor to atom O2i (symmetry code: -x+1/2, y+1/2, z) forming a C(7) chain running parallel to the [010] direction (Fig. 2).

Related literature top

For the graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995). For related structures, see: Gowda et al. (2008); Zhou & Zheng (2007); Khan et al. (2010). Benzamide derivatives are frequently used in the synthesis of new and effective anti-convulsant agents, see: Clark et al. (1988); Leander et al. (1988); Diouf et al. (1997). For bond-length data, see: Allen et al. (1987).

Experimental top

A solution of methyl anthranilate (390 µl, 3 mmol) in dichloromethane (15 ml) was treated dropwise with 4-chlorobenzoyl chloride (383 µl, 3 mmol) in the presence of triethanolamine (5 ml) as a catalyst. The resulting mixture was stirred for 1 h. On completion of reaction, precipitates formed, were filtered, dried and crystallized from methanol to yield colorless blocks of the title compound.

Refinement top

All H-atoms were refined using riding model for hydrogen bonds with d(C—H) = 0.93Å (Uiso=1.2Ueq of the parent atom) for aromatic carbon atoms, d(N—H) = 0.86Å (Uiso=1.2Ueq of the parent atom) for imine nitrogen atom and d(C—H) = 0.96Å (Uiso=1.5Ueq of the parent atom) for methyl carbon atom.

Structure description top

Benzamide derivatives are frequently used in the synthesis of new and effective anti-convulsant agents (Clark et al., 1988; Leander et al., 1988; Diouf et al., 1997). In continuation of our ongoing structural studies of benzamide derivatives (Khan et al., 2010), herein the crystal structure of title compound is described.

In the title compound, Fig. 1, the C1—N1—C9(O1)—C10 amide unit is planar, r.m.s. deviation 0.0102 Å, and subtends dihedral angles of 3.42 (2)° and 6.60 (2)° respectively to the C1···C6 and C10···C15 rings. The two aromatic rings are inclined at 3.32 (3)°. Bond distances within the molecule are normal (Allen et al. 1987) and similar to those observed in comparable structures (Gowda et al. 2008; Zhou & Zheng 2007).

The intramolecular C2—H2···O1 and N1—H1···O2 hydrogen bonds produce S(6) rings (Bernstein et al., 1995) (Fig. 1). The C3—H3 group in the molecule at acts as a hydrogen-bond donor to atom O2i (symmetry code: -x+1/2, y+1/2, z) forming a C(7) chain running parallel to the [010] direction (Fig. 2).

For the graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995). For related structures, see: Gowda et al. (2008); Zhou & Zheng (2007); Khan et al. (2010). Benzamide derivatives are frequently used in the synthesis of new and effective anti-convulsant agents, see: Clark et al. (1988); Leander et al. (1988); Diouf et al. (1997). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. A view of the title compound showing displacement ellipsoids drawn at the 30% probability level. Hydrogen bonds are indicated by dashed lines.
[Figure 2] Fig. 2. Part of the crystal structure, showing the formation of a C(7) chain running parallel to the [010] direction. For the sake of clarity, H atoms not involved in the motif shown have been omitted (symmetry code: i = -x+1/2, y+1/2, z)).
Methyl 2-(4-chlorobenzamido)benzoate top
Crystal data top
C15H12ClNO3F(000) = 1200
Mr = 289.71Dx = 1.446 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 11747 reflections
a = 7.3788 (9) Åθ = 3.1–16.8°
b = 16.757 (2) ŵ = 0.29 mm−1
c = 21.530 (2) ÅT = 296 K
V = 2662.0 (5) Å3Block, colorless
Z = 80.21 × 0.12 × 0.08 mm
Data collection top
Bruker SMART APEXII
diffractometer		814 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.166
Graphite monochromatorθmax = 25.2°, θmin = 3.1°
φ and ω scansh = −9→5
11139 measured reflectionsk = −20→20
2399 independent reflectionsl = −26→23
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0301P)2]
where P = (Fo2 + 2Fc2)/3
2399 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Crystal data top
C15H12ClNO3V = 2662.0 (5) Å3
Mr = 289.71Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 7.3788 (9) ŵ = 0.29 mm−1
b = 16.757 (2) ÅT = 296 K
c = 21.530 (2) Å0.21 × 0.12 × 0.08 mm
Data collection top
Bruker SMART APEXII
diffractometer		814 reflections with I > 2σ(I)
11139 measured reflectionsRint = 0.166
2399 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.134H-atom parameters constrained
S = 0.97Δρmax = 0.21 e Å−3
2399 reflectionsΔρmin = −0.26 e Å−3
182 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C10.2912 (7)0.0979 (3)0.5068 (2)0.0455 (14)
C20.3378 (8)0.1763 (3)0.5195 (2)0.0592 (16)
H20.39270.18920.55710.071*
C30.3031 (8)0.2348 (3)0.4770 (3)0.0663 (17)
H30.33570.28720.48570.080*
C40.2209 (7)0.2174 (3)0.4215 (3)0.0637 (17)
H40.19550.25800.39330.076*
C50.1760 (7)0.1399 (3)0.4076 (2)0.0533 (16)
H50.12130.12810.36980.064*
C60.2116 (7)0.0788 (3)0.4498 (2)0.0425 (14)
C70.1648 (7)−0.0040 (3)0.4327 (2)0.0487 (16)
C80.0594 (7)−0.0888 (3)0.3536 (2)0.0757 (19)
H8A0.1720−0.11360.34240.113*
H8B−0.0180−0.08610.31780.113*
H8C0.0013−0.11960.38550.113*
C90.3924 (7)0.0410 (3)0.6083 (2)0.0522 (16)
C100.4046 (7)−0.0374 (3)0.6420 (2)0.0447 (14)
C110.3391 (7)−0.1095 (3)0.6209 (2)0.0515 (16)
H110.2803−0.11180.58270.062*
C120.3590 (7)−0.1781 (3)0.6552 (2)0.0559 (16)
H120.3158−0.22650.64010.067*
C130.4442 (7)−0.1741 (3)0.7124 (2)0.0523 (15)
C140.5107 (7)−0.1034 (3)0.7343 (2)0.0571 (16)
H140.5693−0.10130.77250.069*
C150.4904 (7)−0.0356 (3)0.6994 (2)0.0557 (16)
H150.53490.01260.71450.067*
N10.3251 (5)0.0360 (2)0.54958 (18)0.0502 (12)
H10.2999−0.01130.53680.060*
O10.4375 (6)0.1027 (2)0.63322 (15)0.0849 (14)
O20.1871 (5)−0.06159 (18)0.46533 (15)0.0636 (12)
O30.0940 (5)−0.00921 (19)0.37634 (15)0.0615 (11)
Cl10.4671 (2)−0.25964 (8)0.75727 (6)0.0747 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.043 (4)0.042 (3)0.051 (4)0.003 (3)0.009 (3)−0.003 (3)
C20.073 (5)0.050 (4)0.054 (4)−0.003 (3)0.004 (3)−0.004 (3)
C30.085 (5)0.041 (3)0.073 (4)−0.003 (4)0.008 (4)−0.006 (3)
C40.070 (5)0.051 (4)0.070 (4)0.013 (4)0.012 (4)0.008 (3)
C50.054 (5)0.052 (4)0.054 (4)0.004 (3)0.004 (3)0.006 (3)
C60.039 (4)0.047 (3)0.041 (3)0.001 (3)0.005 (3)0.005 (3)
C70.048 (5)0.054 (4)0.044 (4)0.000 (4)0.001 (3)0.004 (3)
C80.110 (6)0.056 (4)0.061 (4)−0.006 (4)−0.022 (4)−0.008 (3)
C90.054 (5)0.058 (4)0.045 (4)0.001 (3)−0.001 (3)−0.008 (3)
C100.042 (4)0.060 (4)0.033 (3)0.003 (3)0.003 (3)−0.006 (3)
C110.057 (5)0.061 (4)0.037 (3)−0.001 (3)−0.010 (3)−0.001 (3)
C120.064 (5)0.055 (4)0.049 (4)0.008 (3)0.000 (3)−0.008 (3)
C130.054 (5)0.056 (4)0.047 (4)0.014 (3)0.010 (3)0.006 (3)
C140.054 (5)0.075 (4)0.042 (3)0.006 (4)−0.003 (3)−0.002 (3)
C150.059 (5)0.065 (4)0.043 (4)−0.005 (3)0.006 (3)−0.009 (3)
N10.060 (4)0.046 (3)0.044 (3)−0.002 (2)−0.006 (2)−0.002 (2)
O10.132 (4)0.061 (3)0.062 (3)−0.015 (3)−0.023 (2)−0.008 (2)
O20.094 (4)0.043 (2)0.054 (2)−0.005 (2)−0.020 (2)0.0071 (18)
O30.085 (4)0.049 (2)0.051 (2)−0.006 (2)−0.015 (2)0.0026 (18)
Cl10.0844 (13)0.0744 (10)0.0654 (9)0.0159 (10)−0.0047 (9)0.0112 (8)
Geometric parameters (Å, º) top
C1—C21.386 (6)C8—H8C0.9600
C1—C61.398 (6)C9—O11.212 (5)
C1—N11.410 (5)C9—N11.360 (5)
C2—C31.365 (6)C9—C101.503 (6)
C2—H20.9300C10—C111.379 (6)
C3—C41.371 (6)C10—C151.388 (6)
C3—H30.9300C11—C121.373 (6)
C4—C51.373 (6)C11—H110.9300
C4—H40.9300C12—C131.385 (6)
C5—C61.393 (6)C12—H120.9300
C5—H50.9300C13—C141.367 (6)
C6—C71.476 (6)C13—Cl11.737 (5)
C7—O21.206 (5)C14—C151.370 (6)
C7—O31.323 (5)C14—H140.9300
C8—O31.443 (5)C15—H150.9300
C8—H8A0.9600N1—H10.8600
C8—H8B0.9600
C2—C1—C6119.7 (5)H8B—C8—H8C109.5
C2—C1—N1121.6 (5)O1—C9—N1124.3 (5)
C6—C1—N1118.7 (4)O1—C9—C10121.0 (5)
C3—C2—C1120.1 (5)N1—C9—C10114.7 (5)
C3—C2—H2120.0C11—C10—C15118.2 (5)
C1—C2—H2120.0C11—C10—C9125.8 (5)
C2—C3—C4121.0 (5)C15—C10—C9116.0 (5)
C2—C3—H3119.5C12—C11—C10121.3 (5)
C4—C3—H3119.5C12—C11—H11119.4
C3—C4—C5119.8 (5)C10—C11—H11119.4
C3—C4—H4120.1C11—C12—C13119.1 (5)
C5—C4—H4120.1C11—C12—H12120.5
C4—C5—C6120.5 (5)C13—C12—H12120.5
C4—C5—H5119.7C14—C13—C12120.8 (5)
C6—C5—H5119.7C14—C13—Cl1119.3 (4)
C5—C6—C1118.9 (5)C12—C13—Cl1120.0 (5)
C5—C6—C7119.0 (5)C13—C14—C15119.4 (5)
C1—C6—C7122.2 (5)C13—C14—H14120.3
O2—C7—O3122.3 (5)C15—C14—H14120.3
O2—C7—C6125.1 (5)C14—C15—C10121.3 (5)
O3—C7—C6112.5 (4)C14—C15—H15119.4
O3—C8—H8A109.5C10—C15—H15119.4
O3—C8—H8B109.5C9—N1—C1128.8 (4)
H8A—C8—H8B109.5C9—N1—H1115.6
O3—C8—H8C109.5C1—N1—H1115.6
H8A—C8—H8C109.5C7—O3—C8116.2 (4)
C6—C1—C2—C31.1 (8)N1—C9—C10—C15173.4 (4)
N1—C1—C2—C3179.9 (5)C15—C10—C11—C12−0.6 (8)
C1—C2—C3—C40.6 (9)C9—C10—C11—C12179.3 (5)
C2—C3—C4—C5−1.5 (9)C10—C11—C12—C131.0 (8)
C3—C4—C5—C60.7 (9)C11—C12—C13—C14−1.1 (8)
C4—C5—C6—C11.0 (8)C11—C12—C13—Cl1178.7 (4)
C4—C5—C6—C7−178.8 (5)C12—C13—C14—C150.9 (8)
C2—C1—C6—C5−1.9 (8)Cl1—C13—C14—C15−179.0 (4)
N1—C1—C6—C5179.3 (4)C13—C14—C15—C10−0.5 (8)
C2—C1—C6—C7177.8 (5)C11—C10—C15—C140.3 (8)
N1—C1—C6—C7−1.0 (7)C9—C10—C15—C14−179.6 (5)
C5—C6—C7—O2−179.1 (5)O1—C9—N1—C1−1.1 (9)
C1—C6—C7—O21.1 (8)C10—C9—N1—C1177.8 (4)
C5—C6—C7—O30.9 (7)C2—C1—N1—C94.7 (8)
C1—C6—C7—O3−178.8 (5)C6—C1—N1—C9−176.5 (5)
O1—C9—C10—C11172.5 (5)O2—C7—O3—C8−5.4 (7)
N1—C9—C10—C11−6.5 (7)C6—C7—O3—C8174.6 (4)
O1—C9—C10—C15−7.7 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.932.212.839 (6)124
N1—H1···O20.861.942.646 (5)138
C3—H3···O2i0.932.583.422 (6)151
Symmetry code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC15H12ClNO3
Mr289.71
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)296
a, b, c (Å)7.3788 (9), 16.757 (2), 21.530 (2)
V (Å3)2662.0 (5)
Z8
Radiation typeMo Kα
µ (mm−1)0.29
Crystal size (mm)0.21 × 0.12 × 0.08
Data collection
DiffractometerBruker SMART APEXII
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		11139, 2399, 814
Rint0.166
(sin θ/λ)max (Å−1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.134, 0.97
No. of reflections2399
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.21, −0.26

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.932.212.839 (6)124
N1—H1···O20.861.942.646 (5)138
C3—H3···O2i0.932.583.422 (6)151
Symmetry code: (i) −x+1/2, y+1/2, z.
 

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer.

References

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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3338
https://doi.org/10.1107/S160053681004897X
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