organic compounds
Methyl 2-(3-chlorobenzamido)benzoate
aLaboratoire de Chimie Bio-organique et Macromoléculaire, Faculté des Sciences et Techniques Guéliz, Marrakech, Morocco, bUnité de Chimie Biomoléculaire et Médicinale, Faculté des Sciences Semlalia, Marrakech, Morocco, cLaboratoire de la Matière Condensée et des Nanostructures, Faculté des Sciences et Techniques Guéliz, Marrakech, Morocco, and dLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: a_ouahrouch@yahoo.fr
In the molecule of the title compound, C15H12ClNO3, the chlorobenzamide and benzoate units are almost co-planar, with a dihedral angle between the six-membered rings of 2.99 (10)°. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, each molecule 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 molecules, with an interplanar 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
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell 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).
Supporting information
10.1107/S1600536812046934/zl2515sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812046934/zl2515Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812046934/zl2515Isup3.cml
In the first step, follwowing a literature procedure (Xingwen et al., 2007; Chandrika et al., 2008) anthranilic acid (2-amino benzoic acid) was reacted with benzoyl chloride in dry pyridine at 273 K for 4 h to obtain 2-(3-chlorophenyl)-benzo[d][1,3] oxazin-4-one in good yield (75%). This products was then mixed with 0.5 eq of potassium carbonate in methanol to form the title compound in close to quantitative yield. The crude product was purified by passing through a column packed with silica gel. The solvent used for δ (ppm): 3.95 (s, 3H, -OCH3), 7.08-7.14 (m, 1H, H-Aromatic), 7.40-7.61 (m, 3H, H-Aromatic), 7.86 (d, 1H, H-Aromatic), 8.02-8.07 (m, 2H, H-Aromatic), 8.85 (m, 1H, H-Aromatic), 11.90 (s, 1H, -NH-). 13C NMR (300 MHz, CDCl3) δ (ppm): 52.54 (-OCH3), 120.47, 122.89, 125.10, 128.05, 130.05, 130.98, 131.94, 134.84 (CH-Aromatic), 115.28, 135.10, 136.71, 141.56 (C-Aromatic), 164.45 (CO), 169.05 (CO).
was methylene chloride. A colourless crystal suitable for X-ray analysis was obtained by slow evaporation of a solution in methanol. The compound was characterized by 1H and 13C NMR and its structure was confirmed by X-ray 1H NMR (300 MHz, CDCl3)H atoms were located in a difference map and treated as riding with C—H = 0.96 Å, C—H = 0.97 Å, C—H = 0.93 Å and N—H = 0.86 Å for methyl, methylene, aromatic CH and NH respectively. All hydrogen atoms were refined with Uiso(H) = 1.2 Ueq (aromatic, methylene) or Uiso(H) = 1.5 Ueq for methyl.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).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 |
C15H12ClNO3 | V = 2717.10 (16) Å3 |
Mr = 289.71 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 25.7464 (10) Å | µ = 0.29 mm−1 |
b = 6.9203 (2) Å | T = 296 K |
c = 16.9735 (6) Å | 0.36 × 0.31 × 0.27 mm |
β = 116.045 (2)° |
Bruker X8 APEXII diffractometer | 3511 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2143 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.997 | Rint = 0.038 |
20126 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.31 e Å−3 |
3511 reflections | Δρmin = −0.40 e Å−3 |
181 parameters |
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 |
Symmetry code: (i) −x+2, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H12ClNO3 |
Mr | 289.71 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 296 |
a, b, c (Å) | 25.7464 (10), 6.9203 (2), 16.9735 (6) |
β (°) | 116.045 (2) |
V (Å3) | 2717.10 (16) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.36 × 0.31 × 0.27 |
Data collection | |
Diffractometer | Bruker X8 APEXII diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.957, 0.997 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20126, 3511, 2143 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.676 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.144, 1.02 |
No. of reflections | 3511 |
No. of parameters | 181 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.40 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al. 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H2···O2 | 0.86 | 1.96 | 2.6506 (19) | 136.6 |
C1—H1···O1i | 0.93 | 2.67 | 3.573 (2) | 162.7 |
C9—H9···Cl1i | 0.93 | 2.87 | 3.617 (2) | 138.6 |
Symmetry code: (i) −x+2, y, −z+1/2. |
Acknowledgements
The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Benzoxazinone derivatives were found to be inhibitors of standard serine proteases of the chrymotrypsin superfamily (Kurosaki & Naishi, 1983, Ponchet et al., 1988) and inhibit by formation of an acyl-enzyme complex through attack of the active site serine on the carbonyl group (Hedsrom et al., 1984, Krantz et al., 1990). The benzoxazinone derivatives have two available sites for nucleophilic attack. The two sites have partial positive charges that can guide different types of nucleophiles towards the opening of the heterocyles of the benzoxazinone derivatives. In general, benzoxazinone derivatives show good reactivity towards substitution reactions at position number 2 of the heterocycle and at positions 5, 6, 7 and 8 of the aromatic ring (Shariat & Abdollahi 2004). In connection to our studies on the synthesis of new bis-hyterocyclic compounds with different substituents, we decided to attempt to open the benzoxazinone heterocycle under basic conditions. Ring opening of 2-(3-chlorophenyl)-benzo[d][1,3] oxazin-4-one with potassium carbonate in methanol yielded the title compound.
The crystal structure of the methyl-2-(3-chlorobenzamido)benzoate features two aromatic six-membered rings (C1 to C6 and C8 to C13) which are, as expected, virtually planar, with maximum deviations of 0.006 (2) Å and -0.004 (2) Å for C1 and C9, respectively as shown in Fig.1. Moreover, the two rings are nearly coplanar as indicated by the dihedral angle between them of 2.99 (10) °. The two rings are linked through a connecting amide group with a C6—C7—N1—C8 dihedral angle of 174.71 (17)° (anti-periplanar conformation).
The cohesion of the molecules in the crystal structure is ensured by C1—H1···O1 and C9—H9···Cl1 non classic weak hydrogen bonds between symmetry equivalent molecules across a twofold rotation axis, forming dimers (Fig.2 and Table 2, symmetry operator (i) -x+2, y, -z+1/2). The structure is further stabilized by weak π–π stacking interactions between inversion-related molecules (symmetry operator (ii) -x+2, -y+1, -z+1), with an interplanar distance of 3.46 (2) Å and a centroid–centroid vector of 3.897 (2) Å, leading to formation of π-stacked columns of inversion-related molecules along the direction of the b-axis.