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organic compounds
N-(2,6-Dimethylphenyl)benzamide
aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, bFaculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and cInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com
The title compound, C15H15NO, crystallizes with two molecules in the The H—N—C=O units are in a trans conformation, similar to that observed in N-(3,4-dimethylphenyl)benzamide, N-(2,6-dichlorophenyl)benzamide and other benzanilides. The central –NHCO– bridging unit is tilted at angles of 17.1 (3) and 16.4 (3)° to the benzoyl ring in the two molecules. The two rings (benzoyl and aniline) are almost orthogonal with respect to each other, making dihedral angles of 86.3 (1) and 86.0 (1)° in the two molecules. N—H⋯O hydrogen bonds link molecules into infinite chains running along the c axis.
Experimental
Crystal data
|
Refinement
|
|
Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell CrysAlis RED (Oxford Diffraction, 2007
); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: ORTEP-3 (Farrugia, 1997
) and DIAMOND (Brandenburg, 2002
); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003
) and WinGX (Farrugia, 1999
).
Supporting information
10.1107/S1600536808018230/bt2724sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808018230/bt2724Isup2.hkl
The title compound was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.
All H atoms were placed in calculated positions and constrained to ride on their parent atoms, with C–H distances of 0.93Å (C-aromatic), 0.96Å (C-methyl) and N–H distances 0.86 Å. The Uiso(H) values were set at 1.2 Ueq(C,N) and 1.5 Ueq (C-methyl). The displacement parameters of C-atoms in aniline ring of both molecules were restrained by use of the SHELXL97 DELU command with default standard deviations.
Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell
CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).C15H15NO | F(000) = 480 |
Mr = 225.28 | Dx = 1.169 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2 y c | Cell parameters from 18913 reflections |
a = 16.4389 (8) Å | θ = 3.1–29.3° |
b = 8.2903 (4) Å | µ = 0.07 mm−1 |
c = 9.4902 (3) Å | T = 295 K |
β = 98.165 (4)° | Block, colourless |
V = 1280.25 (10) Å3 | 0.52 × 0.46 × 0.22 mm |
Z = 4 |
Oxford Diffraction Xcalibur diffractometer | 2504 independent reflections |
Graphite monochromator | 2110 reflections with I > 2σ(I) |
Detector resolution: 10.434 pixels mm-1 | Rint = 0.059 |
ω scans with κ offsets | θmax = 26.0°, θmin = 5.3° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | h = −20→20 |
Tmin = 0.924, Tmax = 0.985 | k = −10→10 |
38015 measured reflections | l = −11→11 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0851P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.001 |
2504 reflections | Δρmax = 0.13 e Å−3 |
307 parameters | Δρmin = −0.14 e Å−3 |
35 restraints | Absolute structure: Flack (1983), 2493 Friedel pairs |
Primary atom site location: structure-invariant direct methods |
C15H15NO | V = 1280.25 (10) Å3 |
Mr = 225.28 | Z = 4 |
Monoclinic, Pc | Mo Kα radiation |
a = 16.4389 (8) Å | µ = 0.07 mm−1 |
b = 8.2903 (4) Å | T = 295 K |
c = 9.4902 (3) Å | 0.52 × 0.46 × 0.22 mm |
β = 98.165 (4)° |
Oxford Diffraction Xcalibur diffractometer | 2504 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 2110 reflections with I > 2σ(I) |
Tmin = 0.924, Tmax = 0.985 | Rint = 0.059 |
38015 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 35 restraints |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.13 e Å−3 |
2504 reflections | Δρmin = −0.14 e Å−3 |
307 parameters | Absolute structure: Flack (1983), 2493 Friedel pairs |
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 | ||
N1 | 0.32493 (12) | 0.0027 (2) | 0.63912 (17) | 0.0476 (4) | |
H1N | 0.324 | −0.0067 | 0.7291 | 0.057* | |
O1 | 0.27687 (12) | −0.0838 (2) | 0.41847 (15) | 0.0654 (5) | |
C1 | 0.27534 (13) | −0.0900 (2) | 0.5470 (2) | 0.0446 (5) | |
C2 | 0.21752 (13) | −0.2015 (2) | 0.6052 (2) | 0.0435 (5) | |
C3 | 0.15307 (16) | −0.2637 (3) | 0.5109 (2) | 0.0523 (5) | |
H3 | 0.1478 | −0.2349 | 0.4153 | 0.063* | |
C4 | 0.09687 (16) | −0.3669 (3) | 0.5561 (3) | 0.0601 (6) | |
H4 | 0.0532 | −0.4056 | 0.492 | 0.072* | |
C5 | 0.10537 (18) | −0.4130 (3) | 0.6967 (3) | 0.0664 (7) | |
H5 | 0.0679 | −0.4843 | 0.7276 | 0.08* | |
C6 | 0.16901 (17) | −0.3537 (3) | 0.7909 (3) | 0.0655 (7) | |
H6 | 0.1745 | −0.3852 | 0.8859 | 0.079* | |
C7 | 0.22549 (17) | −0.2472 (3) | 0.7468 (2) | 0.0534 (5) | |
H7 | 0.2683 | −0.2068 | 0.8118 | 0.064* | |
C8 | 0.37898 (15) | 0.1165 (3) | 0.5877 (2) | 0.0523 (5) | |
C9 | 0.36263 (18) | 0.2796 (3) | 0.5956 (3) | 0.0611 (6) | |
C10 | 0.4128 (2) | 0.3869 (4) | 0.5370 (4) | 0.0872 (10) | |
H10 | 0.4028 | 0.4971 | 0.5414 | 0.105* | |
C11 | 0.4773 (3) | 0.3323 (6) | 0.4721 (5) | 0.1051 (13) | |
H11 | 0.5097 | 0.4056 | 0.431 | 0.126* | |
C12 | 0.4940 (2) | 0.1719 (6) | 0.4678 (4) | 0.0922 (10) | |
H12 | 0.5382 | 0.1373 | 0.4245 | 0.111* | |
C13 | 0.44632 (17) | 0.0583 (4) | 0.5268 (3) | 0.0714 (7) | |
C14 | 0.46683 (19) | −0.1163 (3) | 0.5241 (4) | 0.0916 (10) | |
H14A | 0.5245 | −0.1288 | 0.5198 | 0.137* | |
H14B | 0.4358 | −0.1657 | 0.4421 | 0.137* | |
H14C | 0.4535 | −0.1671 | 0.6088 | 0.137* | |
C15 | 0.29134 (19) | 0.3401 (3) | 0.6634 (3) | 0.0813 (8) | |
H15A | 0.3035 | 0.329 | 0.7649 | 0.122* | |
H15B | 0.2817 | 0.4516 | 0.6394 | 0.122* | |
H15C | 0.2432 | 0.2782 | 0.6291 | 0.122* | |
N2 | 0.82433 (12) | 0.5011 (2) | 0.52006 (18) | 0.0491 (4) | |
H2N | 0.8272 | 0.4924 | 0.6109 | 0.059* | |
O2 | 0.87411 (12) | 0.4211 (2) | 0.32326 (16) | 0.0615 (5) | |
C21 | 0.87462 (13) | 0.4123 (3) | 0.4518 (2) | 0.0432 (5) | |
C22 | 0.93234 (13) | 0.2984 (2) | 0.5387 (2) | 0.0432 (5) | |
C23 | 0.99704 (15) | 0.2371 (3) | 0.4762 (2) | 0.0524 (5) | |
H23 | 1.0031 | 0.268 | 0.3841 | 0.063* | |
C24 | 1.05223 (16) | 0.1314 (3) | 0.5484 (3) | 0.0617 (6) | |
H24 | 1.0959 | 0.0927 | 0.5058 | 0.074* | |
C25 | 1.04286 (19) | 0.0830 (4) | 0.6833 (3) | 0.0695 (7) | |
H25 | 1.0798 | 0.0102 | 0.7319 | 0.083* | |
C26 | 0.9794 (2) | 0.1416 (4) | 0.7462 (3) | 0.0706 (7) | |
H26 | 0.9733 | 0.1089 | 0.8379 | 0.085* | |
C27 | 0.92362 (17) | 0.2497 (3) | 0.6748 (2) | 0.0552 (6) | |
H27 | 0.8805 | 0.2892 | 0.7185 | 0.066* | |
C28 | 0.76616 (16) | 0.6096 (3) | 0.4456 (3) | 0.0574 (6) | |
C29 | 0.69959 (18) | 0.5439 (5) | 0.3541 (3) | 0.0782 (8) | |
C30 | 0.6445 (3) | 0.6494 (8) | 0.2804 (4) | 0.1161 (14) | |
H30 | 0.5997 | 0.6093 | 0.2198 | 0.139* | |
C31 | 0.6549 (4) | 0.8115 (8) | 0.2950 (5) | 0.1338 (18) | |
H31 | 0.6174 | 0.8807 | 0.2432 | 0.161* | |
C32 | 0.7200 (3) | 0.8750 (5) | 0.3850 (5) | 0.1149 (14) | |
H32 | 0.7256 | 0.9862 | 0.3944 | 0.138* | |
C33 | 0.7778 (2) | 0.7734 (4) | 0.4626 (3) | 0.0749 (8) | |
C34 | 0.8494 (3) | 0.8415 (4) | 0.5588 (4) | 0.0956 (11) | |
H34A | 0.8985 | 0.7854 | 0.5439 | 0.143* | |
H34B | 0.8406 | 0.8288 | 0.6561 | 0.143* | |
H34C | 0.855 | 0.954 | 0.5383 | 0.143* | |
C35 | 0.6868 (2) | 0.3667 (5) | 0.3381 (4) | 0.0944 (11) | |
H35A | 0.6348 | 0.3462 | 0.2812 | 0.142* | |
H35B | 0.6876 | 0.3186 | 0.4303 | 0.142* | |
H35C | 0.73 | 0.3209 | 0.2924 | 0.142* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0636 (11) | 0.0502 (11) | 0.0299 (8) | −0.0042 (8) | 0.0098 (7) | −0.0009 (7) |
O1 | 0.0973 (13) | 0.0703 (11) | 0.0302 (8) | −0.0220 (9) | 0.0143 (8) | −0.0006 (7) |
C1 | 0.0622 (13) | 0.0405 (11) | 0.0317 (10) | 0.0035 (9) | 0.0088 (9) | 0.0025 (8) |
C2 | 0.0584 (12) | 0.0382 (10) | 0.0354 (10) | 0.0056 (9) | 0.0121 (9) | −0.0022 (8) |
C3 | 0.0676 (14) | 0.0524 (12) | 0.0370 (10) | 0.0002 (11) | 0.0074 (10) | −0.0012 (9) |
C4 | 0.0624 (14) | 0.0608 (15) | 0.0580 (14) | −0.0097 (12) | 0.0113 (11) | −0.0109 (11) |
C5 | 0.0785 (16) | 0.0621 (15) | 0.0651 (16) | −0.0169 (13) | 0.0318 (13) | −0.0066 (12) |
C6 | 0.0941 (19) | 0.0658 (15) | 0.0404 (12) | −0.0114 (14) | 0.0224 (12) | 0.0041 (11) |
C7 | 0.0704 (15) | 0.0549 (13) | 0.0356 (10) | −0.0044 (11) | 0.0096 (10) | 0.0001 (9) |
C8 | 0.0583 (12) | 0.0603 (14) | 0.0375 (11) | −0.0109 (10) | 0.0040 (9) | 0.0008 (9) |
C9 | 0.0758 (16) | 0.0583 (14) | 0.0465 (13) | −0.0119 (12) | −0.0011 (11) | 0.0019 (10) |
C10 | 0.112 (2) | 0.0695 (19) | 0.077 (2) | −0.0283 (17) | 0.0019 (18) | 0.0093 (15) |
C11 | 0.102 (3) | 0.116 (3) | 0.099 (3) | −0.047 (2) | 0.021 (2) | 0.018 (2) |
C12 | 0.0732 (18) | 0.118 (3) | 0.089 (2) | −0.0255 (19) | 0.0234 (17) | 0.001 (2) |
C13 | 0.0634 (15) | 0.090 (2) | 0.0615 (16) | −0.0082 (14) | 0.0117 (13) | −0.0007 (14) |
C14 | 0.083 (2) | 0.097 (2) | 0.100 (3) | 0.0162 (18) | 0.0284 (18) | −0.0079 (19) |
C15 | 0.116 (2) | 0.0602 (16) | 0.0685 (17) | 0.0098 (16) | 0.0150 (16) | 0.0055 (14) |
N2 | 0.0646 (11) | 0.0517 (11) | 0.0318 (9) | 0.0042 (9) | 0.0095 (7) | 0.0007 (7) |
O2 | 0.0854 (11) | 0.0690 (11) | 0.0316 (8) | 0.0136 (8) | 0.0131 (7) | 0.0056 (7) |
C21 | 0.0534 (11) | 0.0406 (11) | 0.0354 (11) | −0.0037 (9) | 0.0056 (9) | 0.0006 (8) |
C22 | 0.0566 (12) | 0.0389 (10) | 0.0337 (10) | −0.0058 (9) | 0.0050 (9) | −0.0026 (8) |
C23 | 0.0650 (14) | 0.0505 (13) | 0.0431 (11) | 0.0003 (11) | 0.0126 (10) | −0.0022 (9) |
C24 | 0.0620 (14) | 0.0627 (15) | 0.0594 (14) | 0.0096 (12) | 0.0054 (11) | −0.0100 (11) |
C25 | 0.0839 (18) | 0.0638 (16) | 0.0554 (15) | 0.0191 (14) | −0.0085 (13) | −0.0017 (12) |
C26 | 0.103 (2) | 0.0713 (16) | 0.0367 (12) | 0.0173 (16) | 0.0076 (12) | 0.0101 (11) |
C27 | 0.0738 (15) | 0.0550 (13) | 0.0378 (11) | 0.0078 (11) | 0.0109 (11) | 0.0026 (10) |
C28 | 0.0638 (14) | 0.0676 (15) | 0.0428 (12) | 0.0141 (11) | 0.0149 (10) | 0.0050 (10) |
C29 | 0.0598 (15) | 0.117 (2) | 0.0581 (16) | 0.0097 (16) | 0.0087 (12) | 0.0036 (16) |
C30 | 0.083 (2) | 0.167 (4) | 0.093 (3) | 0.041 (3) | −0.006 (2) | 0.006 (3) |
C31 | 0.133 (4) | 0.157 (4) | 0.105 (3) | 0.079 (3) | −0.006 (3) | 0.026 (3) |
C32 | 0.163 (4) | 0.086 (2) | 0.098 (3) | 0.058 (3) | 0.025 (3) | 0.015 (2) |
C33 | 0.106 (2) | 0.0647 (17) | 0.0579 (16) | 0.0229 (15) | 0.0245 (15) | 0.0070 (12) |
C34 | 0.155 (3) | 0.0564 (17) | 0.078 (2) | −0.009 (2) | 0.024 (2) | −0.0030 (15) |
C35 | 0.0733 (19) | 0.114 (3) | 0.094 (3) | −0.0303 (19) | 0.0074 (18) | −0.014 (2) |
N1—C1 | 1.348 (3) | N2—C21 | 1.341 (3) |
N1—C8 | 1.429 (3) | N2—C28 | 1.425 (3) |
N1—H1N | 0.86 | N2—H2N | 0.86 |
O1—C1 | 1.225 (2) | O2—C21 | 1.221 (3) |
C1—C2 | 1.487 (3) | C21—C22 | 1.500 (3) |
C2—C3 | 1.385 (3) | C22—C27 | 1.380 (3) |
C2—C7 | 1.385 (3) | C22—C23 | 1.386 (3) |
C3—C4 | 1.373 (4) | C23—C24 | 1.372 (4) |
C3—H3 | 0.93 | C23—H23 | 0.93 |
C4—C5 | 1.376 (4) | C24—C25 | 1.372 (4) |
C4—H4 | 0.93 | C24—H24 | 0.93 |
C5—C6 | 1.368 (4) | C25—C26 | 1.364 (4) |
C5—H5 | 0.93 | C25—H25 | 0.93 |
C6—C7 | 1.389 (4) | C26—C27 | 1.388 (4) |
C6—H6 | 0.93 | C26—H26 | 0.93 |
C7—H7 | 0.93 | C27—H27 | 0.93 |
C8—C9 | 1.383 (4) | C28—C33 | 1.378 (4) |
C8—C13 | 1.405 (4) | C28—C29 | 1.406 (4) |
C9—C10 | 1.382 (4) | C29—C30 | 1.376 (5) |
C9—C15 | 1.501 (4) | C29—C35 | 1.489 (6) |
C10—C11 | 1.376 (6) | C30—C31 | 1.359 (8) |
C10—H10 | 0.93 | C30—H30 | 0.93 |
C11—C12 | 1.360 (6) | C31—C32 | 1.375 (8) |
C11—H11 | 0.93 | C31—H31 | 0.93 |
C12—C13 | 1.392 (5) | C32—C33 | 1.398 (5) |
C12—H12 | 0.93 | C32—H32 | 0.93 |
C13—C14 | 1.488 (4) | C33—C34 | 1.494 (5) |
C14—H14A | 0.96 | C34—H34A | 0.96 |
C14—H14B | 0.96 | C34—H34B | 0.96 |
C14—H14C | 0.96 | C34—H34C | 0.96 |
C15—H15A | 0.96 | C35—H35A | 0.96 |
C15—H15B | 0.96 | C35—H35B | 0.96 |
C15—H15C | 0.9599 | C35—H35C | 0.96 |
C1—N1—C8 | 120.20 (17) | C21—N2—C28 | 121.55 (17) |
C1—N1—H1N | 119.9 | C21—N2—H2N | 119.2 |
C8—N1—H1N | 119.9 | C28—N2—H2N | 119.2 |
O1—C1—N1 | 121.7 (2) | O2—C21—N2 | 122.2 (2) |
O1—C1—C2 | 120.00 (19) | O2—C21—C22 | 120.06 (19) |
N1—C1—C2 | 118.25 (17) | N2—C21—C22 | 117.74 (17) |
C3—C2—C7 | 118.9 (2) | C27—C22—C23 | 118.8 (2) |
C3—C2—C1 | 117.52 (18) | C27—C22—C21 | 123.8 (2) |
C7—C2—C1 | 123.5 (2) | C23—C22—C21 | 117.35 (17) |
C4—C3—C2 | 121.1 (2) | C24—C23—C22 | 120.9 (2) |
C4—C3—H3 | 119.4 | C24—C23—H23 | 119.6 |
C2—C3—H3 | 119.4 | C22—C23—H23 | 119.6 |
C3—C4—C5 | 119.8 (2) | C23—C24—C25 | 120.0 (2) |
C3—C4—H4 | 120.1 | C23—C24—H24 | 120 |
C5—C4—H4 | 120.1 | C25—C24—H24 | 120 |
C6—C5—C4 | 119.8 (2) | C26—C25—C24 | 119.9 (2) |
C6—C5—H5 | 120.1 | C26—C25—H25 | 120 |
C4—C5—H5 | 120.1 | C24—C25—H25 | 120 |
C5—C6—C7 | 120.9 (2) | C25—C26—C27 | 120.7 (2) |
C5—C6—H6 | 119.6 | C25—C26—H26 | 119.7 |
C7—C6—H6 | 119.6 | C27—C26—H26 | 119.7 |
C2—C7—C6 | 119.4 (2) | C22—C27—C26 | 119.8 (2) |
C2—C7—H7 | 120.3 | C22—C27—H27 | 120.1 |
C6—C7—H7 | 120.3 | C26—C27—H27 | 120.1 |
C9—C8—C13 | 121.9 (2) | C33—C28—C29 | 122.5 (3) |
C9—C8—N1 | 119.5 (2) | C33—C28—N2 | 119.5 (3) |
C13—C8—N1 | 118.6 (2) | C29—C28—N2 | 118.1 (3) |
C10—C9—C8 | 118.4 (3) | C30—C29—C28 | 117.8 (4) |
C10—C9—C15 | 120.3 (3) | C30—C29—C35 | 120.2 (4) |
C8—C9—C15 | 121.3 (2) | C28—C29—C35 | 122.1 (3) |
C11—C10—C9 | 120.6 (3) | C31—C30—C29 | 120.8 (4) |
C11—C10—H10 | 119.7 | C31—C30—H30 | 119.6 |
C9—C10—H10 | 119.7 | C29—C30—H30 | 119.6 |
C12—C11—C10 | 120.5 (3) | C30—C31—C32 | 121.1 (4) |
C12—C11—H11 | 119.8 | C30—C31—H31 | 119.4 |
C10—C11—H11 | 119.8 | C32—C31—H31 | 119.4 |
C11—C12—C13 | 121.5 (3) | C31—C32—C33 | 120.5 (4) |
C11—C12—H12 | 119.3 | C31—C32—H32 | 119.8 |
C13—C12—H12 | 119.3 | C33—C32—H32 | 119.8 |
C12—C13—C8 | 117.0 (3) | C28—C33—C32 | 117.3 (4) |
C12—C13—C14 | 120.6 (3) | C28—C33—C34 | 121.9 (3) |
C8—C13—C14 | 122.3 (2) | C32—C33—C34 | 120.8 (3) |
C13—C14—H14A | 109.5 | C33—C34—H34A | 109.5 |
C13—C14—H14B | 109.5 | C33—C34—H34B | 109.5 |
H14A—C14—H14B | 109.5 | H34A—C34—H34B | 109.5 |
C13—C14—H14C | 109.5 | C33—C34—H34C | 109.5 |
H14A—C14—H14C | 109.5 | H34A—C34—H34C | 109.5 |
H14B—C14—H14C | 109.5 | H34B—C34—H34C | 109.5 |
C9—C15—H15A | 109.5 | C29—C35—H35A | 109.5 |
C9—C15—H15B | 109.5 | C29—C35—H35B | 109.5 |
H15A—C15—H15B | 109.5 | H35A—C35—H35B | 109.5 |
C9—C15—H15C | 109.4 | C29—C35—H35C | 109.5 |
H15A—C15—H15C | 109.5 | H35A—C35—H35C | 109.5 |
H15B—C15—H15C | 109.5 | H35B—C35—H35C | 109.5 |
C8—N1—C1—O1 | 2.5 (3) | C28—N2—C21—O2 | 1.0 (3) |
C8—N1—C1—C2 | −177.4 (2) | C28—N2—C21—C22 | −178.5 (2) |
O1—C1—C2—C3 | −16.4 (3) | O2—C21—C22—C27 | −162.8 (2) |
N1—C1—C2—C3 | 163.44 (19) | N2—C21—C22—C27 | 16.7 (3) |
O1—C1—C2—C7 | 162.8 (2) | O2—C21—C22—C23 | 15.9 (3) |
N1—C1—C2—C7 | −17.3 (3) | N2—C21—C22—C23 | −164.55 (19) |
C7—C2—C3—C4 | 1.0 (3) | C27—C22—C23—C24 | −0.8 (3) |
C1—C2—C3—C4 | −179.8 (2) | C21—C22—C23—C24 | −179.6 (2) |
C2—C3—C4—C5 | −1.5 (4) | C22—C23—C24—C25 | 1.2 (4) |
C3—C4—C5—C6 | 1.0 (4) | C23—C24—C25—C26 | −0.9 (4) |
C4—C5—C6—C7 | 0.0 (4) | C24—C25—C26—C27 | 0.3 (5) |
C3—C2—C7—C6 | 0.0 (3) | C23—C22—C27—C26 | 0.2 (3) |
C1—C2—C7—C6 | −179.2 (2) | C21—C22—C27—C26 | 178.9 (2) |
C5—C6—C7—C2 | −0.5 (4) | C25—C26—C27—C22 | 0.1 (4) |
C1—N1—C8—C9 | 108.7 (2) | C21—N2—C28—C33 | −110.2 (3) |
C1—N1—C8—C13 | −69.7 (3) | C21—N2—C28—C29 | 68.3 (3) |
C13—C8—C9—C10 | 2.4 (4) | C33—C28—C29—C30 | −0.3 (4) |
N1—C8—C9—C10 | −175.9 (2) | N2—C28—C29—C30 | −178.8 (3) |
C13—C8—C9—C15 | −178.9 (3) | C33—C28—C29—C35 | −179.0 (3) |
N1—C8—C9—C15 | 2.8 (3) | N2—C28—C29—C35 | 2.5 (4) |
C8—C9—C10—C11 | 0.1 (4) | C28—C29—C30—C31 | 0.6 (6) |
C15—C9—C10—C11 | −178.7 (3) | C35—C29—C30—C31 | 179.4 (4) |
C9—C10—C11—C12 | −1.6 (6) | C29—C30—C31—C32 | −0.9 (8) |
C10—C11—C12—C13 | 0.7 (6) | C30—C31—C32—C33 | 0.8 (8) |
C11—C12—C13—C8 | 1.6 (5) | C29—C28—C33—C32 | 0.3 (4) |
C11—C12—C13—C14 | −178.5 (3) | N2—C28—C33—C32 | 178.7 (3) |
C9—C8—C13—C12 | −3.2 (4) | C29—C28—C33—C34 | −179.2 (3) |
N1—C8—C13—C12 | 175.1 (2) | N2—C28—C33—C34 | −0.8 (4) |
C9—C8—C13—C14 | 176.9 (3) | C31—C32—C33—C28 | −0.5 (6) |
N1—C8—C13—C14 | −4.8 (4) | C31—C32—C33—C34 | 179.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.86 | 2.19 | 2.949 (2) | 147 |
N2—H2N···O2ii | 0.86 | 2.17 | 2.949 (2) | 150 |
Symmetry codes: (i) x, −y, z+1/2; (ii) x, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H15NO |
Mr | 225.28 |
Crystal system, space group | Monoclinic, Pc |
Temperature (K) | 295 |
a, b, c (Å) | 16.4389 (8), 8.2903 (4), 9.4902 (3) |
β (°) | 98.165 (4) |
V (Å3) | 1280.25 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.52 × 0.46 × 0.22 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.924, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 38015, 2504, 2110 |
Rint | 0.059 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.108, 0.98 |
No. of reflections | 2504 |
No. of parameters | 307 |
No. of restraints | 35 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.13, −0.14 |
Absolute structure | Flack (1983), 2493 Friedel pairs |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.86 | 2.19 | 2.949 (2) | 147.4 |
N2—H2N···O2ii | 0.86 | 2.17 | 2.949 (2) | 149.8 |
Symmetry codes: (i) x, −y, z+1/2; (ii) x, −y+1, z+1/2. |
Acknowledgements
MT and JK thank the Grant Agency of the Slovak Republic (VEGA 1/0817/08) and Structural Funds (Interreg IIIA) for financial support in the purchase of the diffractometer.
References
Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230. CAS Google Scholar
Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008a). Acta Cryst. E64, o340. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008b). Acta Cryst. E64, o540. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
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.
In the present work, the structure of N-(2,6-dimethylphenyl)-benzamide (N26DMPBA) has been determined to study the effect of substituents on the solid state geometries of benzanilides (Gowda et al., 2003; Gowda et al., 2008a; Gowda et al., 2008b). The conformations of the N—H and C=O bonds in N26DMPBA (Fig.1) are anti to each other, similar to that observed in N-(3,4-dimethylphenyl)-benzamide (Gowda et al., 2008a), N-(2,6-dichlorophenyl)-benzamide (Gowda et al., 2008b) and other benzanilides (Gowda et al., 2003). The structure of N26DMPBA has two molecules in its asymmetric unit. The central amide group –NHCO– is tilted to the benzoyl ring at the angles of 17.1 (3)° and 16.4 (3)°, in molecule 1 and 2, respectively. The two rings (benzoyl and aniline) are almost orthogonal, with the dihedral angles of 86.3 (1)° and 86.0 (1)° in molecules 1 and 2, respectively.
Part of the crystal structure of the title compound showing molecular chains as viewed down the b axis is shown in Fig.2. Hydrogen bonds N1–H1N···O1(i) and N2–H2N···O2(ii) give rise to infinite molecular chains running along the c axis (Symmetry codes: (i) x,-y,z + 1/2; (ii) x,-y + 1,z + 1/2).