Methyl 2-(3-chloro-benzamido)-benzoate.

In the mol-ecule of the title compound, C15H12ClNO3, the chloro-benzamide and benzoate units are almost co-planar, with a dihedral angle between the six-membered rings of 2.99 (10)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, each mol-ecule is linked to a symmetry-equivalent counterpart across a twofold rotation axis by weak C-H⋯O and C-H⋯Cl hydrogen bonds, forming dimers. The packing is stabilized through weak π-π stacking along the b-axis direction, leading to π-stacked columns of inversion-related mol-ecules, with an inter-planar distance of 3.46 (2) Å and a centroid-centroid vector of 3.897 (2) Å.

Related literature

For details of the synthesis, see: Shariat & Abdollahi (2004 ▶); Xingwen et al. (2007 ▶); Chandrika et al. (2008 ▶). For background to the potential biological use of benzoxazinone derivatives, see: Kurosaki & Naishi (1983 ▶); Ponchet et al. (1988 ▶); Hedsrom et al. (1984 ▶); Krantz et al. (1990 ▶).

Experimental

Crystal data

C15H12ClNO3

M = 289.71

Monoclinic,

a = 25.7464 (10) Å

b = 6.9203 (2) Å

c = 16.9735 (6) Å

β = 116.045 (2)°

V = 2717.10 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.36 × 0.31 × 0.27 mm

Data collection

Bruker X8 APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.957, T max = 0.997

20126 measured reflections

3511 independent reflections

2143 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.144

S = 1.02

3511 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2012 ▶) and Mercury (Macrae et al. 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046934/zl2515sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046934/zl2515Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046934/zl2515Isup3.cml

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

C15H12ClNO3	F(000) = 1200
Mr = 289.71	Dx = 1.416 Mg m−3
Monoclinic, C2/c	Melting point: 361.5 K
Hall symbol: -c 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 25.7464 (10) Å	Cell parameters from 3511 reflections
b = 6.9203 (2) Å	θ = 3.1–28.7°
c = 16.9735 (6) Å	µ = 0.29 mm−1
β = 116.045 (2)°	T = 296 K
V = 2717.10 (16) Å3	Block, colourless
Z = 8	0.36 × 0.31 × 0.27 mm

Bruker X8 APEXII diffractometer	3511 independent reflections
Radiation source: fine-focus sealed tube	2143 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 28.7°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −34→34
Tmin = 0.957, Tmax = 0.997	k = −6→9
20126 measured reflections	l = −22→22

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0663P)2 + 1.0088P] where P = (Fo2 + 2Fc2)/3
3511 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	1.07779 (8)	0.3043 (3)	0.40699 (12)	0.0493 (4)
H1	1.0601	0.3084	0.3460	0.059*
C2	1.13694 (8)	0.3154 (3)	0.45261 (13)	0.0532 (5)
C3	1.16464 (8)	0.3122 (3)	0.54250 (13)	0.0576 (5)
H3	1.2047	0.3199	0.5720	0.069*
C4	1.13189 (9)	0.2973 (3)	0.58835 (13)	0.0598 (5)
H4	1.1500	0.2962	0.6493	0.072*
C5	1.07250 (8)	0.2840 (3)	0.54427 (12)	0.0523 (5)
H5	1.0508	0.2732	0.5758	0.063*
C6	1.04473 (7)	0.2867 (2)	0.45306 (11)	0.0450 (4)
C7	0.98059 (8)	0.2750 (3)	0.40006 (12)	0.0491 (4)
C8	0.89076 (8)	0.2154 (3)	0.41741 (12)	0.0479 (4)
C9	0.85177 (9)	0.2244 (3)	0.32896 (13)	0.0643 (6)
H9	0.8653	0.2354	0.2865	0.077*
C10	0.79331 (9)	0.2169 (4)	0.30448 (14)	0.0770 (7)
H10	0.7677	0.2245	0.2453	0.092*
C11	0.77171 (9)	0.1984 (4)	0.36551 (15)	0.0751 (7)
H11	0.7321	0.1932	0.3479	0.090*
C12	0.80976 (8)	0.1878 (3)	0.45261 (14)	0.0613 (5)
H12	0.7955	0.1743	0.4940	0.074*
C13	0.86918 (8)	0.1966 (3)	0.48050 (11)	0.0470 (4)
C14	0.90870 (8)	0.1895 (3)	0.57552 (12)	0.0497 (4)
C15	0.91577 (12)	0.1812 (5)	0.71856 (14)	0.0935 (9)
H15A	0.8921	0.1509	0.7476	0.112*
H15B	0.9333	0.3057	0.7375	0.112*
H15C	0.9454	0.0851	0.7327	0.112*
N1	0.95046 (6)	0.2249 (2)	0.44555 (10)	0.0496 (4)
H2	0.9712	0.1946	0.4996	0.060*
O1	0.95798 (6)	0.3078 (3)	0.32160 (9)	0.0813 (5)
O2	0.96083 (6)	0.1874 (2)	0.60722 (8)	0.0627 (4)
O3	0.88031 (6)	0.1841 (2)	0.62469 (9)	0.0710 (4)
Cl1	1.17831 (2)	0.33637 (11)	0.39517 (4)	0.0870 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0453 (10)	0.0606 (11)	0.0458 (10)	−0.0014 (8)	0.0234 (8)	−0.0021 (8)
C2	0.0452 (10)	0.0637 (12)	0.0583 (11)	−0.0011 (8)	0.0298 (9)	−0.0003 (9)
C3	0.0397 (10)	0.0745 (13)	0.0562 (11)	−0.0021 (9)	0.0190 (9)	−0.0015 (9)
C4	0.0485 (11)	0.0805 (14)	0.0461 (11)	−0.0045 (10)	0.0169 (9)	−0.0017 (9)
C5	0.0454 (11)	0.0680 (12)	0.0473 (10)	−0.0040 (9)	0.0238 (9)	−0.0012 (8)
C6	0.0406 (9)	0.0493 (9)	0.0479 (10)	−0.0006 (7)	0.0219 (8)	−0.0016 (8)
C7	0.0439 (10)	0.0626 (11)	0.0445 (10)	−0.0023 (8)	0.0228 (8)	−0.0027 (8)
C8	0.0378 (9)	0.0596 (11)	0.0458 (10)	−0.0027 (8)	0.0178 (8)	−0.0009 (8)
C9	0.0446 (11)	0.1000 (16)	0.0459 (11)	−0.0092 (11)	0.0175 (9)	−0.0012 (10)
C10	0.0443 (12)	0.123 (2)	0.0511 (12)	−0.0117 (12)	0.0092 (10)	0.0035 (12)
C11	0.0351 (10)	0.1150 (19)	0.0692 (14)	−0.0091 (11)	0.0173 (10)	0.0055 (13)
C12	0.0434 (11)	0.0823 (14)	0.0628 (12)	−0.0034 (10)	0.0276 (10)	0.0032 (11)
C13	0.0405 (10)	0.0532 (10)	0.0479 (10)	−0.0017 (8)	0.0198 (8)	−0.0001 (8)
C14	0.0472 (11)	0.0575 (11)	0.0495 (10)	−0.0008 (8)	0.0259 (9)	0.0026 (8)
C15	0.0829 (18)	0.157 (3)	0.0497 (13)	0.0046 (17)	0.0375 (13)	0.0061 (14)
N1	0.0364 (8)	0.0701 (10)	0.0430 (8)	0.0001 (7)	0.0180 (7)	0.0044 (7)
O1	0.0493 (9)	0.1499 (15)	0.0442 (8)	−0.0092 (9)	0.0199 (7)	0.0100 (8)
O2	0.0461 (8)	0.0951 (11)	0.0464 (7)	−0.0013 (7)	0.0198 (6)	0.0058 (7)
O3	0.0586 (9)	0.1105 (12)	0.0529 (8)	0.0034 (8)	0.0326 (7)	0.0034 (7)
Cl1	0.0521 (3)	0.1486 (7)	0.0740 (4)	−0.0057 (3)	0.0405 (3)	0.0009 (4)

C1—C2	1.374 (3)	C9—C10	1.375 (3)
C1—C6	1.391 (2)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.380 (3)
C2—C3	1.372 (3)	C10—H10	0.9300
C2—Cl1	1.7374 (18)	C11—C12	1.371 (3)
C3—C4	1.380 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.390 (3)
C4—C5	1.379 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.482 (3)
C5—C6	1.392 (3)	C14—O2	1.207 (2)
C5—H5	0.9300	C14—O3	1.329 (2)
C6—C7	1.496 (3)	C15—O3	1.448 (3)
C7—O1	1.218 (2)	C15—H15A	0.9600
C7—N1	1.358 (2)	C15—H15B	0.9600
C8—C9	1.394 (3)	C15—H15C	0.9600
C8—N1	1.397 (2)	N1—H2	0.8600
C8—C13	1.412 (2)
C2—C1—C6	119.22 (17)	C8—C9—H9	120.0
C2—C1—H1	120.4	C9—C10—C11	121.7 (2)
C6—C1—H1	120.4	C9—C10—H10	119.2
C3—C2—C1	122.16 (17)	C11—C10—H10	119.2
C3—C2—Cl1	118.55 (15)	C12—C11—C10	118.80 (19)
C1—C2—Cl1	119.28 (15)	C12—C11—H11	120.6
C2—C3—C4	118.71 (18)	C10—C11—H11	120.6
C2—C3—H3	120.6	C11—C12—C13	121.57 (19)
C4—C3—H3	120.6	C11—C12—H12	119.2
C5—C4—C3	120.37 (18)	C13—C12—H12	119.2
C5—C4—H4	119.8	C12—C13—C8	119.09 (17)
C3—C4—H4	119.8	C12—C13—C14	119.73 (16)
C4—C5—C6	120.56 (17)	C8—C13—C14	121.17 (16)
C4—C5—H5	119.7	O2—C14—O3	122.00 (17)
C6—C5—H5	119.7	O2—C14—C13	125.66 (16)
C1—C6—C5	118.96 (16)	O3—C14—C13	112.34 (16)
C1—C6—C7	116.94 (16)	O3—C15—H15A	109.5
C5—C6—C7	124.09 (16)	O3—C15—H15B	109.5
O1—C7—N1	123.45 (17)	H15A—C15—H15B	109.5
O1—C7—C6	121.25 (16)	O3—C15—H15C	109.5
N1—C7—C6	115.29 (16)	H15A—C15—H15C	109.5
C9—C8—N1	122.04 (16)	H15B—C15—H15C	109.5
C9—C8—C13	118.94 (17)	C7—N1—C8	129.44 (16)
N1—C8—C13	119.03 (15)	C7—N1—H2	115.3
C10—C9—C8	119.93 (19)	C8—N1—H2	115.3
C10—C9—H9	120.0	C14—O3—C15	115.88 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2···O2	0.86	1.96	2.6506 (19)	137
C1—H1···O1i	0.93	2.67	3.573 (2)	163
C9—H9···Cl1i	0.93	2.87	3.617 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2⋯O2	0.86	1.96	2.6506 (19)	137
C1—H1⋯O1i	0.93	2.67	3.573 (2)	163
C9—H9⋯Cl1i	0.93	2.87	3.617 (2)	139

Symmetry code: (i) .