Methyl 2-(4-chloro-benzamido)-benzoate.

In the title compound, C(15)H(12)ClNO(3), the central C-C(O)-N-C amide unit makes dihedral angles of 6.60 (2) and 3.42 (2)°, respectively, with the 4-chloro-benzene and anilino rings. The dihedral angle between the two benzene rings is 3.32 (3)°. Intra-molecular N-H⋯O and C-H⋯O hydrogen bonds form S(6) rings and contribute to the planarity of this portion of the mol-ecule. In the crystal, inter-molecular C-H⋯O hydrogen bonds are observed, which link the mol-ecules into [010] C(7) chains.

Related literature

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

Crystal data

C15H12ClNO3

M = 289.71

Orthorhombic,

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)

R int = 0.166

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 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

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004897X/om2376Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H12ClNO3	F(000) = 1200
Mr = 289.71	Dx = 1.446 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 11747 reflections
a = 7.3788 (9) Å	θ = 3.1–16.8°
b = 16.757 (2) Å	µ = 0.29 mm−1
c = 21.530 (2) Å	T = 296 K
V = 2662.0 (5) Å3	Block, colorless
Z = 8	0.21 × 0.12 × 0.08 mm

Bruker SMART APEXII diffractometer	814 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.166
graphite	θmax = 25.2°, θmin = 3.1°
φ and ω scans	h = −9→5
11139 measured reflections	k = −20→20
2399 independent reflections	l = −26→23

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-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 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.2912 (7)	0.0979 (3)	0.5068 (2)	0.0455 (14)
C2	0.3378 (8)	0.1763 (3)	0.5195 (2)	0.0592 (16)
H2	0.3927	0.1892	0.5571	0.071*
C3	0.3031 (8)	0.2348 (3)	0.4770 (3)	0.0663 (17)
H3	0.3357	0.2872	0.4857	0.080*
C4	0.2209 (7)	0.2174 (3)	0.4215 (3)	0.0637 (17)
H4	0.1955	0.2580	0.3933	0.076*
C5	0.1760 (7)	0.1399 (3)	0.4076 (2)	0.0533 (16)
H5	0.1213	0.1281	0.3698	0.064*
C6	0.2116 (7)	0.0788 (3)	0.4498 (2)	0.0425 (14)
C7	0.1648 (7)	−0.0040 (3)	0.4327 (2)	0.0487 (16)
C8	0.0594 (7)	−0.0888 (3)	0.3536 (2)	0.0757 (19)
H8A	0.1720	−0.1136	0.3424	0.113*
H8B	−0.0180	−0.0861	0.3178	0.113*
H8C	0.0013	−0.1196	0.3855	0.113*
C9	0.3924 (7)	0.0410 (3)	0.6083 (2)	0.0522 (16)
C10	0.4046 (7)	−0.0374 (3)	0.6420 (2)	0.0447 (14)
C11	0.3391 (7)	−0.1095 (3)	0.6209 (2)	0.0515 (16)
H11	0.2803	−0.1118	0.5827	0.062*
C12	0.3590 (7)	−0.1781 (3)	0.6552 (2)	0.0559 (16)
H12	0.3158	−0.2265	0.6401	0.067*
C13	0.4442 (7)	−0.1741 (3)	0.7124 (2)	0.0523 (15)
C14	0.5107 (7)	−0.1034 (3)	0.7343 (2)	0.0571 (16)
H14	0.5693	−0.1013	0.7725	0.069*
C15	0.4904 (7)	−0.0356 (3)	0.6994 (2)	0.0557 (16)
H15	0.5349	0.0126	0.7145	0.067*
N1	0.3251 (5)	0.0360 (2)	0.54958 (18)	0.0502 (12)
H1	0.2999	−0.0113	0.5368	0.060*
O1	0.4375 (6)	0.1027 (2)	0.63322 (15)	0.0849 (14)
O2	0.1871 (5)	−0.06159 (18)	0.46533 (15)	0.0636 (12)
O3	0.0940 (5)	−0.00921 (19)	0.37634 (15)	0.0615 (11)
Cl1	0.4671 (2)	−0.25964 (8)	0.75727 (6)	0.0747 (6)

	U11	U22	U33	U12	U13	U23
C1	0.043 (4)	0.042 (3)	0.051 (4)	0.003 (3)	0.009 (3)	−0.003 (3)
C2	0.073 (5)	0.050 (4)	0.054 (4)	−0.003 (3)	0.004 (3)	−0.004 (3)
C3	0.085 (5)	0.041 (3)	0.073 (4)	−0.003 (4)	0.008 (4)	−0.006 (3)
C4	0.070 (5)	0.051 (4)	0.070 (4)	0.013 (4)	0.012 (4)	0.008 (3)
C5	0.054 (5)	0.052 (4)	0.054 (4)	0.004 (3)	0.004 (3)	0.006 (3)
C6	0.039 (4)	0.047 (3)	0.041 (3)	0.001 (3)	0.005 (3)	0.005 (3)
C7	0.048 (5)	0.054 (4)	0.044 (4)	0.000 (4)	0.001 (3)	0.004 (3)
C8	0.110 (6)	0.056 (4)	0.061 (4)	−0.006 (4)	−0.022 (4)	−0.008 (3)
C9	0.054 (5)	0.058 (4)	0.045 (4)	0.001 (3)	−0.001 (3)	−0.008 (3)
C10	0.042 (4)	0.060 (4)	0.033 (3)	0.003 (3)	0.003 (3)	−0.006 (3)
C11	0.057 (5)	0.061 (4)	0.037 (3)	−0.001 (3)	−0.010 (3)	−0.001 (3)
C12	0.064 (5)	0.055 (4)	0.049 (4)	0.008 (3)	0.000 (3)	−0.008 (3)
C13	0.054 (5)	0.056 (4)	0.047 (4)	0.014 (3)	0.010 (3)	0.006 (3)
C14	0.054 (5)	0.075 (4)	0.042 (3)	0.006 (4)	−0.003 (3)	−0.002 (3)
C15	0.059 (5)	0.065 (4)	0.043 (4)	−0.005 (3)	0.006 (3)	−0.009 (3)
N1	0.060 (4)	0.046 (3)	0.044 (3)	−0.002 (2)	−0.006 (2)	−0.002 (2)
O1	0.132 (4)	0.061 (3)	0.062 (3)	−0.015 (3)	−0.023 (2)	−0.008 (2)
O2	0.094 (4)	0.043 (2)	0.054 (2)	−0.005 (2)	−0.020 (2)	0.0071 (18)
O3	0.085 (4)	0.049 (2)	0.051 (2)	−0.006 (2)	−0.015 (2)	0.0026 (18)
Cl1	0.0844 (13)	0.0744 (10)	0.0654 (9)	0.0159 (10)	−0.0047 (9)	0.0112 (8)

C1—C2	1.386 (6)	C8—H8C	0.9600
C1—C6	1.398 (6)	C9—O1	1.212 (5)
C1—N1	1.410 (5)	C9—N1	1.360 (5)
C2—C3	1.365 (6)	C9—C10	1.503 (6)
C2—H2	0.9300	C10—C11	1.379 (6)
C3—C4	1.371 (6)	C10—C15	1.388 (6)
C3—H3	0.9300	C11—C12	1.373 (6)
C4—C5	1.373 (6)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.385 (6)
C5—C6	1.393 (6)	C12—H12	0.9300
C5—H5	0.9300	C13—C14	1.367 (6)
C6—C7	1.476 (6)	C13—Cl1	1.737 (5)
C7—O2	1.206 (5)	C14—C15	1.370 (6)
C7—O3	1.323 (5)	C14—H14	0.9300
C8—O3	1.443 (5)	C15—H15	0.9300
C8—H8A	0.9600	N1—H1	0.8600
C8—H8B	0.9600
C2—C1—C6	119.7 (5)	H8B—C8—H8C	109.5
C2—C1—N1	121.6 (5)	O1—C9—N1	124.3 (5)
C6—C1—N1	118.7 (4)	O1—C9—C10	121.0 (5)
C3—C2—C1	120.1 (5)	N1—C9—C10	114.7 (5)
C3—C2—H2	120.0	C11—C10—C15	118.2 (5)
C1—C2—H2	120.0	C11—C10—C9	125.8 (5)
C2—C3—C4	121.0 (5)	C15—C10—C9	116.0 (5)
C2—C3—H3	119.5	C12—C11—C10	121.3 (5)
C4—C3—H3	119.5	C12—C11—H11	119.4
C3—C4—C5	119.8 (5)	C10—C11—H11	119.4
C3—C4—H4	120.1	C11—C12—C13	119.1 (5)
C5—C4—H4	120.1	C11—C12—H12	120.5
C4—C5—C6	120.5 (5)	C13—C12—H12	120.5
C4—C5—H5	119.7	C14—C13—C12	120.8 (5)
C6—C5—H5	119.7	C14—C13—Cl1	119.3 (4)
C5—C6—C1	118.9 (5)	C12—C13—Cl1	120.0 (5)
C5—C6—C7	119.0 (5)	C13—C14—C15	119.4 (5)
C1—C6—C7	122.2 (5)	C13—C14—H14	120.3
O2—C7—O3	122.3 (5)	C15—C14—H14	120.3
O2—C7—C6	125.1 (5)	C14—C15—C10	121.3 (5)
O3—C7—C6	112.5 (4)	C14—C15—H15	119.4
O3—C8—H8A	109.5	C10—C15—H15	119.4
O3—C8—H8B	109.5	C9—N1—C1	128.8 (4)
H8A—C8—H8B	109.5	C9—N1—H1	115.6
O3—C8—H8C	109.5	C1—N1—H1	115.6
H8A—C8—H8C	109.5	C7—O3—C8	116.2 (4)
C6—C1—C2—C3	1.1 (8)	N1—C9—C10—C15	173.4 (4)
N1—C1—C2—C3	179.9 (5)	C15—C10—C11—C12	−0.6 (8)
C1—C2—C3—C4	0.6 (9)	C9—C10—C11—C12	179.3 (5)
C2—C3—C4—C5	−1.5 (9)	C10—C11—C12—C13	1.0 (8)
C3—C4—C5—C6	0.7 (9)	C11—C12—C13—C14	−1.1 (8)
C4—C5—C6—C1	1.0 (8)	C11—C12—C13—Cl1	178.7 (4)
C4—C5—C6—C7	−178.8 (5)	C12—C13—C14—C15	0.9 (8)
C2—C1—C6—C5	−1.9 (8)	Cl1—C13—C14—C15	−179.0 (4)
N1—C1—C6—C5	179.3 (4)	C13—C14—C15—C10	−0.5 (8)
C2—C1—C6—C7	177.8 (5)	C11—C10—C15—C14	0.3 (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—O2	1.1 (8)	C10—C9—N1—C1	177.8 (4)
C5—C6—C7—O3	0.9 (7)	C2—C1—N1—C9	4.7 (8)
C1—C6—C7—O3	−178.8 (5)	C6—C1—N1—C9	−176.5 (5)
O1—C9—C10—C11	172.5 (5)	O2—C7—O3—C8	−5.4 (7)
N1—C9—C10—C11	−6.5 (7)	C6—C7—O3—C8	174.6 (4)
O1—C9—C10—C15	−7.7 (8)

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

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) .