Download citation
Download citation
link to html
In the title mol­ecule, C15H12ClNO3, the planar chloro­phenyl moiety forms a dihedral angle of 60.70 (7)° with the mean plane through the rest of the non-H atoms in the mol­ecule. The carbonyl O atoms are involved in intramolecular N—H...O and C—H...O hydrogen bonds. In the solid state, the mol­ecules exist as centrosymmetric C—H...O hydrogen-bonded dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201807X/ci6167sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680201807X/ci6167Isup2.hkl
Contains datablock I

CCDC reference: 200750

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.065
  • wR factor = 0.174
  • Data-to-parameter ratio = 13.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair,1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Methyl 2-(2-chlorobenzamido)benzoate top
Crystal data top
C15H12ClNO3F(000) = 600
Mr = 289.71Dx = 1.389 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 10.072 (1) Åθ = 10.1–15.4°
b = 12.371 (2) ŵ = 0.28 mm1
c = 11.275 (1) ÅT = 293 K
β = 99.62 (2)°Needle, colourless
V = 1385.1 (3) Å30.38 × 0.26 × 0.18 mm
Z = 4
Data collection top
Enraf-Nonius CAD-4
diffractometer
1236 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 25.0°, θmin = 2.5°
ω–2θ scansh = 011
Absorption correction: ψ scan
(North et al., 1968)
k = 014
Tmin = 0.868, Tmax = 0.998l = 1313
2571 measured reflections3 standard reflections every 60 min
2425 independent reflections intensity decay: none
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0851P)2 + 0.2726P]
where P = (Fo2 + 2Fc2)/3
2425 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.29 e Å3
Special details top

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
Cl0.36609 (13)0.17615 (12)0.56552 (12)0.1027 (6)
N10.0388 (3)0.3216 (2)0.3613 (2)0.0514 (8)
H1N0.02510.28020.37590.062*
O10.2026 (3)0.2912 (2)0.4170 (3)0.0747 (8)
O20.3269 (2)0.4354 (2)0.4361 (3)0.0732 (8)
O30.2593 (3)0.3147 (2)0.3392 (3)0.0863 (10)
C10.0036 (3)0.4294 (3)0.3435 (3)0.0462 (8)
C20.1233 (3)0.4653 (3)0.3667 (3)0.0480 (9)
C30.1576 (4)0.5726 (3)0.3510 (3)0.0577 (10)
H30.23990.59610.36840.069*
C40.0725 (4)0.6464 (3)0.3099 (4)0.0672 (11)
H40.09740.71860.29890.081*
C50.0492 (4)0.6112 (3)0.2857 (4)0.0660 (11)
H50.10690.66040.25820.079*
C60.0881 (4)0.5054 (3)0.3010 (3)0.0558 (10)
H60.17090.48370.28320.067*
C70.2173 (3)0.3875 (3)0.4089 (3)0.0530 (9)
C80.4227 (4)0.3636 (4)0.4805 (5)0.0936 (16)
H8A0.44870.30700.42300.140*
H8B0.50100.40400.49190.140*
H8C0.38150.33260.55570.140*
C90.1577 (4)0.2711 (3)0.3596 (3)0.0535 (9)
C100.1525 (4)0.1517 (3)0.3859 (3)0.0535 (9)
C110.0538 (5)0.0891 (3)0.3198 (4)0.0707 (12)
H110.01190.12200.26360.085*
C120.0505 (6)0.0213 (4)0.3354 (5)0.0909 (14)
H120.01520.06270.28830.109*
C130.1439 (6)0.0693 (4)0.4201 (5)0.0887 (15)
H130.14150.14380.43080.106*
C140.2412 (5)0.0096 (4)0.4898 (4)0.0801 (13)
H140.30400.04290.54840.096*
C150.2453 (4)0.1019 (3)0.4719 (4)0.0631 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0889 (9)0.1074 (11)0.1003 (10)0.0067 (7)0.0176 (7)0.0232 (8)
N10.0443 (17)0.0452 (18)0.067 (2)0.0002 (14)0.0157 (14)0.0060 (14)
O10.0628 (18)0.0531 (18)0.115 (2)0.0007 (14)0.0349 (16)0.0090 (16)
O20.0484 (15)0.0731 (19)0.104 (2)0.0023 (14)0.0300 (15)0.0000 (16)
O30.0552 (17)0.0677 (19)0.143 (3)0.0051 (14)0.0382 (18)0.0310 (18)
C10.0445 (19)0.048 (2)0.0465 (19)0.0003 (16)0.0089 (15)0.0007 (17)
C20.045 (2)0.048 (2)0.051 (2)0.0024 (16)0.0063 (16)0.0015 (16)
C30.052 (2)0.051 (2)0.070 (3)0.0071 (19)0.0081 (19)0.0040 (19)
C40.075 (3)0.044 (2)0.081 (3)0.005 (2)0.009 (2)0.009 (2)
C50.072 (3)0.052 (3)0.076 (3)0.007 (2)0.017 (2)0.011 (2)
C60.054 (2)0.056 (2)0.060 (2)0.0003 (19)0.0155 (19)0.0028 (18)
C70.043 (2)0.057 (3)0.058 (2)0.0047 (18)0.0058 (17)0.0018 (19)
C80.068 (3)0.094 (4)0.131 (4)0.003 (3)0.053 (3)0.007 (3)
C90.049 (2)0.052 (2)0.061 (2)0.0079 (19)0.0148 (18)0.0101 (18)
C100.053 (2)0.061 (2)0.050 (2)0.0072 (19)0.0199 (18)0.0066 (19)
C110.081 (3)0.060 (3)0.072 (3)0.003 (2)0.016 (2)0.006 (2)
C120.117 (4)0.070 (3)0.087 (3)0.008 (3)0.020 (3)0.007 (3)
C130.128 (5)0.053 (3)0.094 (4)0.006 (3)0.042 (3)0.007 (3)
C140.098 (4)0.067 (3)0.080 (3)0.026 (3)0.030 (3)0.027 (2)
C150.069 (3)0.065 (3)0.059 (2)0.010 (2)0.021 (2)0.014 (2)
Geometric parameters (Å, º) top
Cl—C151.735 (4)C5—H50.93
N1—C91.354 (4)C6—H60.93
N1—C11.386 (4)C8—H8A0.96
N1—H1N0.86C8—H8B0.96
O1—C71.202 (4)C8—H8C0.96
O2—C71.333 (4)C9—C101.509 (5)
O2—C81.461 (5)C10—C151.375 (5)
O3—C91.213 (4)C10—C111.377 (5)
C1—C61.405 (5)C11—C121.378 (6)
C1—C21.419 (5)C11—H110.93
C2—C31.375 (5)C12—C131.360 (6)
C2—C71.483 (5)C12—H120.93
C3—C41.385 (5)C13—C141.366 (6)
C3—H30.93C13—H130.93
C4—C51.371 (5)C14—C151.396 (6)
C4—H40.93C14—H140.93
C5—C61.368 (5)
Cl···N1i3.494 (3)O3···C8ii3.385 (5)
Cl···C1i3.463 (4)O3···C12vi3.595 (7)
Cl···C8ii3.392 (5)O3···C13vi3.537 (7)
N1···C3iii3.517 (4)C1···C2iii3.537 (5)
O1···C4iv3.598 (5)C1···C3iii3.534 (5)
O2···C6iii3.567 (4)C5···C7iii3.574 (5)
O2···C12v3.525 (6)C6···C7iii3.567 (5)
C9—N1—C1130.4 (3)O2—C8—H8B109.5
C9—N1—H1N114.8H8A—C8—H8B109.5
C1—N1—H1N114.8O2—C8—H8C109.5
C7—O2—C8115.4 (3)H8A—C8—H8C109.5
N1—C1—C6122.6 (3)H8B—C8—H8C109.5
N1—C1—C2119.4 (3)O3—C9—N1125.0 (3)
C6—C1—C2118.0 (3)O3—C9—C10122.1 (3)
C3—C2—C1119.5 (3)N1—C9—C10112.9 (3)
C3—C2—C7120.5 (3)C15—C10—C11118.3 (4)
C1—C2—C7119.9 (3)C15—C10—C9122.4 (4)
C2—C3—C4121.6 (4)C11—C10—C9119.3 (3)
C2—C3—H3119.2C10—C11—C12121.2 (5)
C4—C3—H3119.2C10—C11—H11119.4
C5—C4—C3118.8 (4)C12—C11—H11119.4
C5—C4—H4120.6C13—C12—C11119.6 (5)
C3—C4—H4120.6C13—C12—H12120.2
C6—C5—C4121.7 (4)C11—C12—H12120.2
C6—C5—H5119.2C12—C13—C14120.9 (5)
C4—C5—H5119.2C12—C13—H13119.6
C5—C6—C1120.4 (3)C14—C13—H13119.6
C5—C6—H6119.8C13—C14—C15119.1 (4)
C1—C6—H6119.8C13—C14—H14120.4
O1—C7—O2121.2 (4)C15—C14—H14120.4
O1—C7—C2126.3 (3)C10—C15—C14120.8 (4)
O2—C7—C2112.5 (3)C10—C15—Cl121.1 (3)
O2—C8—H8A109.5C14—C15—Cl118.1 (4)
C9—N1—C1—C69.9 (6)C1—C2—C7—O2174.8 (3)
C9—N1—C1—C2171.2 (3)C1—N1—C9—O31.0 (6)
N1—C1—C2—C3178.9 (3)C1—N1—C9—C10179.0 (3)
C6—C1—C2—C32.1 (5)O3—C9—C10—C1551.3 (5)
N1—C1—C2—C70.4 (5)N1—C9—C10—C15128.7 (4)
C6—C1—C2—C7178.6 (3)O3—C9—C10—C11127.0 (4)
C1—C2—C3—C41.7 (5)N1—C9—C10—C1153.0 (5)
C7—C2—C3—C4179.0 (4)C15—C10—C11—C122.6 (6)
C2—C3—C4—C50.7 (6)C9—C10—C11—C12175.7 (4)
C3—C4—C5—C60.1 (6)C10—C11—C12—C132.0 (7)
C4—C5—C6—C10.6 (6)C11—C12—C13—C140.2 (8)
N1—C1—C6—C5179.5 (3)C12—C13—C14—C151.0 (7)
C2—C1—C6—C51.6 (5)C11—C10—C15—C141.4 (6)
C8—O2—C7—O12.5 (6)C9—C10—C15—C14176.8 (4)
C8—O2—C7—C2178.9 (3)C11—C10—C15—Cl175.8 (3)
C3—C2—C7—O1174.0 (4)C9—C10—C15—Cl5.9 (5)
C1—C2—C7—O16.7 (6)C13—C14—C15—C100.3 (6)
C3—C2—C7—O24.5 (5)C13—C14—C15—Cl177.6 (3)
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1, y, z; (iii) x, y+1, z+1; (iv) x1/2, y1/2, z+1/2; (v) x1/2, y+1/2, z+1/2; (vi) x+1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.861.932.639 (4)139
C6—H6···O30.932.322.912 (5)121
C13—H13···O1vii0.932.513.300 (6)143
Symmetry code: (vii) x, y, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds