In the title molecule, C
15H
12ClNO
3, 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
CCDC reference: 200750
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C15H12ClNO3 | F(000) = 600 |
Mr = 289.71 | Dx = 1.389 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 10.072 (1) Å | θ = 10.1–15.4° |
b = 12.371 (2) Å | µ = 0.28 mm−1 |
c = 11.275 (1) Å | T = 293 K |
β = 99.62 (2)° | Needle, colourless |
V = 1385.1 (3) Å3 | 0.38 × 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 tube | Rint = 0.033 |
Graphite monochromator | θmax = 25.0°, θmin = 2.5° |
ω–2θ scans | h = 0→11 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→14 |
Tmin = 0.868, Tmax = 0.998 | l = −13→13 |
2571 measured reflections | 3 standard reflections every 60 min |
2425 independent reflections | intensity decay: none |
Refinement top
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.174 | H-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 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl | 0.36609 (13) | 0.17615 (12) | 0.56552 (12) | 0.1027 (6) | |
N1 | 0.0388 (3) | 0.3216 (2) | 0.3613 (2) | 0.0514 (8) | |
H1N | −0.0251 | 0.2802 | 0.3759 | 0.062* | |
O1 | −0.2026 (3) | 0.2912 (2) | 0.4170 (3) | 0.0747 (8) | |
O2 | −0.3269 (2) | 0.4354 (2) | 0.4361 (3) | 0.0732 (8) | |
O3 | 0.2593 (3) | 0.3147 (2) | 0.3392 (3) | 0.0863 (10) | |
C1 | 0.0036 (3) | 0.4294 (3) | 0.3435 (3) | 0.0462 (8) | |
C2 | −0.1233 (3) | 0.4653 (3) | 0.3667 (3) | 0.0480 (9) | |
C3 | −0.1576 (4) | 0.5726 (3) | 0.3510 (3) | 0.0577 (10) | |
H3 | −0.2399 | 0.5961 | 0.3684 | 0.069* | |
C4 | −0.0725 (4) | 0.6464 (3) | 0.3099 (4) | 0.0672 (11) | |
H4 | −0.0974 | 0.7186 | 0.2989 | 0.081* | |
C5 | 0.0492 (4) | 0.6112 (3) | 0.2857 (4) | 0.0660 (11) | |
H5 | 0.1069 | 0.6604 | 0.2582 | 0.079* | |
C6 | 0.0881 (4) | 0.5054 (3) | 0.3010 (3) | 0.0558 (10) | |
H6 | 0.1709 | 0.4837 | 0.2832 | 0.067* | |
C7 | −0.2173 (3) | 0.3875 (3) | 0.4089 (3) | 0.0530 (9) | |
C8 | −0.4227 (4) | 0.3636 (4) | 0.4805 (5) | 0.0936 (16) | |
H8A | −0.4487 | 0.3070 | 0.4230 | 0.140* | |
H8B | −0.5010 | 0.4040 | 0.4919 | 0.140* | |
H8C | −0.3815 | 0.3326 | 0.5557 | 0.140* | |
C9 | 0.1577 (4) | 0.2711 (3) | 0.3596 (3) | 0.0535 (9) | |
C10 | 0.1525 (4) | 0.1517 (3) | 0.3859 (3) | 0.0535 (9) | |
C11 | 0.0538 (5) | 0.0891 (3) | 0.3198 (4) | 0.0707 (12) | |
H11 | −0.0119 | 0.1220 | 0.2636 | 0.085* | |
C12 | 0.0505 (6) | −0.0213 (4) | 0.3354 (5) | 0.0909 (14) | |
H12 | −0.0152 | −0.0627 | 0.2883 | 0.109* | |
C13 | 0.1439 (6) | −0.0693 (4) | 0.4201 (5) | 0.0887 (15) | |
H13 | 0.1415 | −0.1438 | 0.4308 | 0.106* | |
C14 | 0.2412 (5) | −0.0096 (4) | 0.4898 (4) | 0.0801 (13) | |
H14 | 0.3040 | −0.0429 | 0.5484 | 0.096* | |
C15 | 0.2453 (4) | 0.1019 (3) | 0.4719 (4) | 0.0631 (10) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl | 0.0889 (9) | 0.1074 (11) | 0.1003 (10) | −0.0067 (7) | −0.0176 (7) | 0.0232 (8) |
N1 | 0.0443 (17) | 0.0452 (18) | 0.067 (2) | −0.0002 (14) | 0.0157 (14) | 0.0060 (14) |
O1 | 0.0628 (18) | 0.0531 (18) | 0.115 (2) | −0.0007 (14) | 0.0349 (16) | 0.0090 (16) |
O2 | 0.0484 (15) | 0.0731 (19) | 0.104 (2) | 0.0023 (14) | 0.0300 (15) | 0.0000 (16) |
O3 | 0.0552 (17) | 0.0677 (19) | 0.143 (3) | 0.0051 (14) | 0.0382 (18) | 0.0310 (18) |
C1 | 0.0445 (19) | 0.048 (2) | 0.0465 (19) | −0.0003 (16) | 0.0089 (15) | −0.0007 (17) |
C2 | 0.045 (2) | 0.048 (2) | 0.051 (2) | −0.0024 (16) | 0.0063 (16) | 0.0015 (16) |
C3 | 0.052 (2) | 0.051 (2) | 0.070 (3) | 0.0071 (19) | 0.0081 (19) | −0.0040 (19) |
C4 | 0.075 (3) | 0.044 (2) | 0.081 (3) | 0.005 (2) | 0.009 (2) | 0.009 (2) |
C5 | 0.072 (3) | 0.052 (3) | 0.076 (3) | −0.007 (2) | 0.017 (2) | 0.011 (2) |
C6 | 0.054 (2) | 0.056 (2) | 0.060 (2) | −0.0003 (19) | 0.0155 (19) | 0.0028 (18) |
C7 | 0.043 (2) | 0.057 (3) | 0.058 (2) | 0.0047 (18) | 0.0058 (17) | −0.0018 (19) |
C8 | 0.068 (3) | 0.094 (4) | 0.131 (4) | −0.003 (3) | 0.053 (3) | 0.007 (3) |
C9 | 0.049 (2) | 0.052 (2) | 0.061 (2) | 0.0079 (19) | 0.0148 (18) | 0.0101 (18) |
C10 | 0.053 (2) | 0.061 (2) | 0.050 (2) | 0.0072 (19) | 0.0199 (18) | 0.0066 (19) |
C11 | 0.081 (3) | 0.060 (3) | 0.072 (3) | 0.003 (2) | 0.016 (2) | 0.006 (2) |
C12 | 0.117 (4) | 0.070 (3) | 0.087 (3) | −0.008 (3) | 0.020 (3) | −0.007 (3) |
C13 | 0.128 (5) | 0.053 (3) | 0.094 (4) | 0.006 (3) | 0.042 (3) | 0.007 (3) |
C14 | 0.098 (4) | 0.067 (3) | 0.080 (3) | 0.026 (3) | 0.030 (3) | 0.027 (2) |
C15 | 0.069 (3) | 0.065 (3) | 0.059 (2) | 0.010 (2) | 0.021 (2) | 0.014 (2) |
Geometric parameters (Å, º) top
Cl—C15 | 1.735 (4) | C5—H5 | 0.93 |
N1—C9 | 1.354 (4) | C6—H6 | 0.93 |
N1—C1 | 1.386 (4) | C8—H8A | 0.96 |
N1—H1N | 0.86 | C8—H8B | 0.96 |
O1—C7 | 1.202 (4) | C8—H8C | 0.96 |
O2—C7 | 1.333 (4) | C9—C10 | 1.509 (5) |
O2—C8 | 1.461 (5) | C10—C15 | 1.375 (5) |
O3—C9 | 1.213 (4) | C10—C11 | 1.377 (5) |
C1—C6 | 1.405 (5) | C11—C12 | 1.378 (6) |
C1—C2 | 1.419 (5) | C11—H11 | 0.93 |
C2—C3 | 1.375 (5) | C12—C13 | 1.360 (6) |
C2—C7 | 1.483 (5) | C12—H12 | 0.93 |
C3—C4 | 1.385 (5) | C13—C14 | 1.366 (6) |
C3—H3 | 0.93 | C13—H13 | 0.93 |
C4—C5 | 1.371 (5) | C14—C15 | 1.396 (6) |
C4—H4 | 0.93 | C14—H14 | 0.93 |
C5—C6 | 1.368 (5) | | |
| | | |
Cl···N1i | 3.494 (3) | O3···C8ii | 3.385 (5) |
Cl···C1i | 3.463 (4) | O3···C12vi | 3.595 (7) |
Cl···C8ii | 3.392 (5) | O3···C13vi | 3.537 (7) |
N1···C3iii | 3.517 (4) | C1···C2iii | 3.537 (5) |
O1···C4iv | 3.598 (5) | C1···C3iii | 3.534 (5) |
O2···C6iii | 3.567 (4) | C5···C7iii | 3.574 (5) |
O2···C12v | 3.525 (6) | C6···C7iii | 3.567 (5) |
| | | |
C9—N1—C1 | 130.4 (3) | O2—C8—H8B | 109.5 |
C9—N1—H1N | 114.8 | H8A—C8—H8B | 109.5 |
C1—N1—H1N | 114.8 | O2—C8—H8C | 109.5 |
C7—O2—C8 | 115.4 (3) | H8A—C8—H8C | 109.5 |
N1—C1—C6 | 122.6 (3) | H8B—C8—H8C | 109.5 |
N1—C1—C2 | 119.4 (3) | O3—C9—N1 | 125.0 (3) |
C6—C1—C2 | 118.0 (3) | O3—C9—C10 | 122.1 (3) |
C3—C2—C1 | 119.5 (3) | N1—C9—C10 | 112.9 (3) |
C3—C2—C7 | 120.5 (3) | C15—C10—C11 | 118.3 (4) |
C1—C2—C7 | 119.9 (3) | C15—C10—C9 | 122.4 (4) |
C2—C3—C4 | 121.6 (4) | C11—C10—C9 | 119.3 (3) |
C2—C3—H3 | 119.2 | C10—C11—C12 | 121.2 (5) |
C4—C3—H3 | 119.2 | C10—C11—H11 | 119.4 |
C5—C4—C3 | 118.8 (4) | C12—C11—H11 | 119.4 |
C5—C4—H4 | 120.6 | C13—C12—C11 | 119.6 (5) |
C3—C4—H4 | 120.6 | C13—C12—H12 | 120.2 |
C6—C5—C4 | 121.7 (4) | C11—C12—H12 | 120.2 |
C6—C5—H5 | 119.2 | C12—C13—C14 | 120.9 (5) |
C4—C5—H5 | 119.2 | C12—C13—H13 | 119.6 |
C5—C6—C1 | 120.4 (3) | C14—C13—H13 | 119.6 |
C5—C6—H6 | 119.8 | C13—C14—C15 | 119.1 (4) |
C1—C6—H6 | 119.8 | C13—C14—H14 | 120.4 |
O1—C7—O2 | 121.2 (4) | C15—C14—H14 | 120.4 |
O1—C7—C2 | 126.3 (3) | C10—C15—C14 | 120.8 (4) |
O2—C7—C2 | 112.5 (3) | C10—C15—Cl | 121.1 (3) |
O2—C8—H8A | 109.5 | C14—C15—Cl | 118.1 (4) |
| | | |
C9—N1—C1—C6 | 9.9 (6) | C1—C2—C7—O2 | 174.8 (3) |
C9—N1—C1—C2 | −171.2 (3) | C1—N1—C9—O3 | −1.0 (6) |
N1—C1—C2—C3 | 178.9 (3) | C1—N1—C9—C10 | 179.0 (3) |
C6—C1—C2—C3 | −2.1 (5) | O3—C9—C10—C15 | 51.3 (5) |
N1—C1—C2—C7 | −0.4 (5) | N1—C9—C10—C15 | −128.7 (4) |
C6—C1—C2—C7 | 178.6 (3) | O3—C9—C10—C11 | −127.0 (4) |
C1—C2—C3—C4 | 1.7 (5) | N1—C9—C10—C11 | 53.0 (5) |
C7—C2—C3—C4 | −179.0 (4) | C15—C10—C11—C12 | −2.6 (6) |
C2—C3—C4—C5 | −0.7 (6) | C9—C10—C11—C12 | 175.7 (4) |
C3—C4—C5—C6 | 0.1 (6) | C10—C11—C12—C13 | 2.0 (7) |
C4—C5—C6—C1 | −0.6 (6) | C11—C12—C13—C14 | −0.2 (8) |
N1—C1—C6—C5 | −179.5 (3) | C12—C13—C14—C15 | −1.0 (7) |
C2—C1—C6—C5 | 1.6 (5) | C11—C10—C15—C14 | 1.4 (6) |
C8—O2—C7—O1 | 2.5 (6) | C9—C10—C15—C14 | −176.8 (4) |
C8—O2—C7—C2 | −178.9 (3) | C11—C10—C15—Cl | −175.8 (3) |
C3—C2—C7—O1 | 174.0 (4) | C9—C10—C15—Cl | 5.9 (5) |
C1—C2—C7—O1 | −6.7 (6) | C13—C14—C15—C10 | 0.3 (6) |
C3—C2—C7—O2 | −4.5 (5) | C13—C14—C15—Cl | 177.6 (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) −x−1/2, y−1/2, −z+1/2; (v) −x−1/2, y+1/2, −z+1/2; (vi) −x+1/2, y+1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.86 | 1.93 | 2.639 (4) | 139 |
C6—H6···O3 | 0.93 | 2.32 | 2.912 (5) | 121 |
C13—H13···O1vii | 0.93 | 2.51 | 3.300 (6) | 143 |
Symmetry code: (vii) −x, −y, −z+1. |