organic compounds
N-(3,4-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 conformation of the NH bond in the structure of the title compound (N34DMPBA), C15H15NO, is anti to the meta-methyl substituent in the aniline ring, similar to that observed with respect to the meta-chloro substituent in N-(3,4-dichlorophenyl)benzamide (N34DCPBA), but in contrast to the syn conformation observed with respect to the meta-methyl substituent in N-(3,4-dimethylphenyl)acetamide. The bond parameters in N34DMPBA are similar to those in N34DCPBA and other benzanilides. The molecules in N34DMPBA are packed into a column-like structure in the direction of the a axis through N—H⋯O hydrogen bonds.
Related literature
For related literature, see: Gowda, Foro & Fuess (2007); Gowda et al. (2003); Gowda, Sowmya et al. (2007).
Experimental
Crystal data
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Data collection
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Refinement
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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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); 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
https://doi.org/10.1107/S1600536807066937/dn2302sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807066937/dn2302Isup2.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.
H atoms bonded to C atoms were placed in geometrically calculated positions and subsequently treated as riding with C–H distance 0.93Å for ring, 0.96Å for methyl. H(N) atom was visible in difference map. In the
the N–H distance was restrained to 0.86 (5) Å. The Uiso(H) values were set at 1.2 Ueq(C,N) of the parent atom (1.5 for methyl).In the present work, the structure of N-(3,4-dimethylphenyl)-benzamide (N34DMPBA) has been determined to explore the effect of substituents on the structure of N-aromatic
(Gowda et al., 2003; Gowda, Sowmya et al., 2007; Gowda, Foro & Fuess, 2007). The conformation of the N—H bond in N34DMPBA (FIg. 1) is anti to the meta methyl substituent in the aniline phenyl ring, similar to that observed with respect to the meta chloro substituent in N-(3,4-dichlorophenyl)-benzamide (N34DCPBA) (Gowda, Sowmya et al., 2007), but in contrast to the syn conformation observed with respect to the meta methyl substituent in the N-(3,4-dimethylphenyl)- acetamide (Gowda, Foro & Fuess, 2007). The bond parameters in N34DMPBA are similar to those in N34DCPBA and other benzanilides (Gowda et al., 2003). The molecules in N34DMPBA are packed into Column like s tructure in the direction of a axis through N—H···O hydrogen bonds (Table 1 & Fig. 2).For related literature, see: Gowda, Foro & Fuess (2007); Gowda et al. (2003); Gowda, Sowmya et al. (2007).
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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).C15H15NO | F(000) = 960 |
Mr = 225.28 | Dx = 1.174 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 6829 reflections |
a = 9.1082 (2) Å | θ = 3.0–29.5° |
b = 9.8123 (2) Å | µ = 0.07 mm−1 |
c = 28.5126 (8) Å | T = 295 K |
V = 2548.24 (10) Å3 | Prism, colourless |
Z = 8 | 0.33 × 0.11 × 0.08 mm |
Oxford Diffraction Xcalibur System diffractometer | 1448 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.035 |
Graphite monochromator | θmax = 26.2°, θmin = 5.1° |
Detector resolution: 10.4340 pixels mm-1 | h = −11→9 |
ω scans with κ offsets | k = −12→12 |
21605 measured reflections | l = −32→35 |
2527 independent reflections |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.194 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | w = 1/[σ2(Fo2) + (0.1315P)2] where P = (Fo2 + 2Fc2)/3 |
2527 reflections | (Δ/σ)max < 0.001 |
159 parameters | Δρmax = 0.37 e Å−3 |
3 restraints | Δρmin = −0.19 e Å−3 |
C15H15NO | V = 2548.24 (10) Å3 |
Mr = 225.28 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 9.1082 (2) Å | µ = 0.07 mm−1 |
b = 9.8123 (2) Å | T = 295 K |
c = 28.5126 (8) Å | 0.33 × 0.11 × 0.08 mm |
Oxford Diffraction Xcalibur System diffractometer | 1448 reflections with I > 2σ(I) |
21605 measured reflections | Rint = 0.035 |
2527 independent reflections |
R[F2 > 2σ(F2)] = 0.058 | 3 restraints |
wR(F2) = 0.194 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.37 e Å−3 |
2527 reflections | Δρmin = −0.19 e Å−3 |
159 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 | 0.1683 (2) | 0.51852 (17) | 0.15178 (7) | 0.0543 (5) | |
C2 | 0.04493 (19) | 0.58368 (18) | 0.17772 (7) | 0.0526 (5) | |
C3 | −0.0315 (2) | 0.5050 (2) | 0.21000 (8) | 0.0651 (6) | |
H3 | −0.0063 | 0.4139 | 0.2141 | 0.078* | |
C4 | −0.1439 (3) | 0.5599 (2) | 0.23587 (9) | 0.0762 (7) | |
H4 | −0.1931 | 0.5068 | 0.2578 | 0.091* | |
C5 | −0.1835 (3) | 0.6937 (2) | 0.22926 (9) | 0.0766 (7) | |
H5 | −0.2602 | 0.7307 | 0.2466 | 0.092* | |
C6 | −0.1109 (2) | 0.7724 (2) | 0.19736 (9) | 0.0724 (7) | |
H6 | −0.1384 | 0.8627 | 0.1929 | 0.087* | |
C7 | 0.0038 (2) | 0.71760 (19) | 0.17159 (8) | 0.0608 (6) | |
H7 | 0.0534 | 0.7717 | 0.1500 | 0.073* | |
C8 | 0.4041 (2) | 0.55741 (19) | 0.11157 (8) | 0.0631 (6) | |
C9 | 0.4082 (3) | 0.4574 (2) | 0.07867 (8) | 0.0728 (7) | |
H9 | 0.3209 | 0.4171 | 0.0690 | 0.087* | |
C10 | 0.5432 (3) | 0.4126 (2) | 0.05859 (8) | 0.0762 (7) | |
C11 | 0.6702 (3) | 0.4749 (2) | 0.07412 (9) | 0.0804 (7) | |
C12 | 0.6653 (3) | 0.5762 (3) | 0.10680 (10) | 0.0874 (8) | |
H12 | 0.7520 | 0.6175 | 0.1165 | 0.105* | |
C13 | 0.5336 (2) | 0.6185 (3) | 0.12574 (10) | 0.0751 (7) | |
H13 | 0.5319 | 0.6878 | 0.1480 | 0.090* | |
C14 | 0.8200 (4) | 0.4325 (3) | 0.05424 (14) | 0.1195 (12) | |
H14A | 0.8943 | 0.4939 | 0.0655 | 0.179* | |
H14B | 0.8169 | 0.4358 | 0.0206 | 0.179* | |
H14C | 0.8426 | 0.3415 | 0.0642 | 0.179* | |
C15 | 0.5398 (4) | 0.3011 (3) | 0.02331 (12) | 0.1179 (11) | |
H15A | 0.6176 | 0.3142 | 0.0010 | 0.177* | |
H15B | 0.4471 | 0.3020 | 0.0073 | 0.177* | |
H15C | 0.5525 | 0.2150 | 0.0388 | 0.177* | |
N1 | 0.26924 (19) | 0.60131 (17) | 0.13237 (7) | 0.0614 (5) | |
H1N | 0.268 (2) | 0.685 (2) | 0.1389 (8) | 0.074* | |
O1 | 0.17788 (16) | 0.39356 (13) | 0.14930 (6) | 0.0777 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0539 (11) | 0.0379 (10) | 0.0710 (13) | −0.0013 (8) | −0.0095 (9) | 0.0014 (8) |
C2 | 0.0473 (11) | 0.0428 (11) | 0.0677 (13) | −0.0043 (7) | −0.0114 (9) | 0.0008 (8) |
C3 | 0.0660 (14) | 0.0438 (11) | 0.0854 (15) | −0.0053 (9) | −0.0009 (11) | 0.0047 (10) |
C4 | 0.0789 (16) | 0.0630 (14) | 0.0869 (16) | −0.0100 (11) | 0.0189 (13) | 0.0031 (11) |
C5 | 0.0701 (15) | 0.0670 (15) | 0.0927 (17) | 0.0000 (11) | 0.0149 (12) | −0.0082 (12) |
C6 | 0.0709 (14) | 0.0501 (11) | 0.0963 (16) | 0.0082 (10) | 0.0072 (13) | −0.0006 (11) |
C7 | 0.0604 (12) | 0.0439 (11) | 0.0781 (14) | −0.0018 (9) | 0.0001 (10) | 0.0058 (10) |
C8 | 0.0752 (15) | 0.0450 (11) | 0.0692 (13) | 0.0032 (10) | 0.0047 (11) | 0.0064 (10) |
C9 | 0.0859 (17) | 0.0577 (13) | 0.0748 (14) | −0.0017 (11) | −0.0030 (12) | 0.0058 (11) |
C10 | 0.107 (2) | 0.0519 (13) | 0.0697 (15) | 0.0122 (12) | 0.0034 (13) | 0.0056 (11) |
C11 | 0.0936 (19) | 0.0621 (14) | 0.0855 (16) | 0.0091 (12) | 0.0067 (14) | 0.0044 (12) |
C12 | 0.0704 (16) | 0.0881 (17) | 0.1036 (19) | 0.0007 (13) | 0.0041 (14) | −0.0054 (15) |
C13 | 0.0639 (14) | 0.0710 (15) | 0.0903 (17) | −0.0011 (11) | 0.0054 (12) | −0.0065 (12) |
C14 | 0.106 (2) | 0.108 (2) | 0.145 (3) | 0.0300 (18) | 0.039 (2) | 0.0006 (19) |
C15 | 0.174 (3) | 0.085 (2) | 0.095 (2) | 0.0096 (18) | 0.011 (2) | −0.0201 (16) |
N1 | 0.0628 (11) | 0.0394 (9) | 0.0821 (12) | 0.0001 (8) | 0.0098 (9) | −0.0019 (8) |
O1 | 0.0706 (10) | 0.0401 (9) | 0.1224 (14) | 0.0007 (6) | 0.0090 (9) | 0.0026 (8) |
C1—O1 | 1.231 (2) | C9—C10 | 1.425 (4) |
C1—N1 | 1.346 (2) | C9—H9 | 0.9300 |
C1—C2 | 1.490 (3) | C10—C11 | 1.382 (4) |
C2—C7 | 1.377 (3) | C10—C15 | 1.487 (4) |
C2—C3 | 1.389 (3) | C11—C12 | 1.363 (4) |
C3—C4 | 1.372 (3) | C11—C14 | 1.535 (4) |
C3—H3 | 0.9300 | C12—C13 | 1.379 (4) |
C4—C5 | 1.374 (3) | C12—H12 | 0.9300 |
C4—H4 | 0.9300 | C13—H13 | 0.9300 |
C5—C6 | 1.364 (3) | C14—H14A | 0.9600 |
C5—H5 | 0.9300 | C14—H14B | 0.9600 |
C6—C7 | 1.386 (3) | C14—H14C | 0.9600 |
C6—H6 | 0.9300 | C15—H15A | 0.9600 |
C7—H7 | 0.9300 | C15—H15B | 0.9600 |
C8—C9 | 1.358 (3) | C15—H15C | 0.9600 |
C8—C13 | 1.384 (3) | N1—H1N | 0.84 (2) |
C8—N1 | 1.430 (3) | ||
O1—C1—N1 | 121.96 (18) | C11—C10—C9 | 117.2 (2) |
O1—C1—C2 | 120.61 (17) | C11—C10—C15 | 124.1 (3) |
N1—C1—C2 | 117.41 (15) | C9—C10—C15 | 118.7 (3) |
C7—C2—C3 | 118.57 (18) | C12—C11—C10 | 120.9 (2) |
C7—C2—C1 | 123.48 (17) | C12—C11—C14 | 118.6 (3) |
C3—C2—C1 | 117.95 (16) | C10—C11—C14 | 120.4 (3) |
C4—C3—C2 | 120.78 (19) | C11—C12—C13 | 121.0 (2) |
C4—C3—H3 | 119.6 | C11—C12—H12 | 119.5 |
C2—C3—H3 | 119.6 | C13—C12—H12 | 119.5 |
C3—C4—C5 | 119.8 (2) | C12—C13—C8 | 119.8 (2) |
C3—C4—H4 | 120.1 | C12—C13—H13 | 120.1 |
C5—C4—H4 | 120.1 | C8—C13—H13 | 120.1 |
C6—C5—C4 | 120.3 (2) | C11—C14—H14A | 109.5 |
C6—C5—H5 | 119.8 | C11—C14—H14B | 109.5 |
C4—C5—H5 | 119.8 | H14A—C14—H14B | 109.5 |
C5—C6—C7 | 120.0 (2) | C11—C14—H14C | 109.5 |
C5—C6—H6 | 120.0 | H14A—C14—H14C | 109.5 |
C7—C6—H6 | 120.0 | H14B—C14—H14C | 109.5 |
C2—C7—C6 | 120.50 (19) | C10—C15—H15A | 109.5 |
C2—C7—H7 | 119.7 | C10—C15—H15B | 109.5 |
C6—C7—H7 | 119.7 | H15A—C15—H15B | 109.5 |
C9—C8—C13 | 119.4 (2) | C10—C15—H15C | 109.5 |
C9—C8—N1 | 121.9 (2) | H15A—C15—H15C | 109.5 |
C13—C8—N1 | 118.7 (2) | H15B—C15—H15C | 109.5 |
C8—C9—C10 | 121.6 (2) | C1—N1—C8 | 125.11 (16) |
C8—C9—H9 | 119.2 | C1—N1—H1N | 119.4 (16) |
C10—C9—H9 | 119.2 | C8—N1—H1N | 113.3 (16) |
O1—C1—C2—C7 | −161.5 (2) | C8—C9—C10—C15 | 179.0 (2) |
N1—C1—C2—C7 | 19.9 (3) | C9—C10—C11—C12 | −0.9 (4) |
O1—C1—C2—C3 | 19.0 (3) | C15—C10—C11—C12 | −179.6 (2) |
N1—C1—C2—C3 | −159.59 (19) | C9—C10—C11—C14 | 180.0 (2) |
C7—C2—C3—C4 | −1.2 (3) | C15—C10—C11—C14 | 1.3 (4) |
C1—C2—C3—C4 | 178.3 (2) | C10—C11—C12—C13 | 0.8 (4) |
C2—C3—C4—C5 | 1.3 (4) | C14—C11—C12—C13 | 179.9 (3) |
C3—C4—C5—C6 | −0.5 (4) | C11—C12—C13—C8 | 0.1 (4) |
C4—C5—C6—C7 | −0.3 (4) | C9—C8—C13—C12 | −0.7 (3) |
C3—C2—C7—C6 | 0.4 (3) | N1—C8—C13—C12 | 178.9 (2) |
C1—C2—C7—C6 | −179.1 (2) | O1—C1—N1—C8 | −7.0 (3) |
C5—C6—C7—C2 | 0.3 (3) | C2—C1—N1—C8 | 171.52 (18) |
C13—C8—C9—C10 | 0.6 (3) | C9—C8—N1—C1 | 51.0 (3) |
N1—C8—C9—C10 | −179.02 (19) | C13—C8—N1—C1 | −128.6 (2) |
C8—C9—C10—C11 | 0.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.84 (2) | 2.12 (2) | 2.948 (2) | 165 (2) |
Symmetry code: (i) −x+1/2, y+1/2, z. |
Experimental details
Crystal data | |
Chemical formula | C15H15NO |
Mr | 225.28 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 295 |
a, b, c (Å) | 9.1082 (2), 9.8123 (2), 28.5126 (8) |
V (Å3) | 2548.24 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.33 × 0.11 × 0.08 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur System |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21605, 2527, 1448 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.621 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.194, 0.97 |
No. of reflections | 2527 |
No. of parameters | 159 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.37, −0.19 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.84 (2) | 2.12 (2) | 2.948 (2) | 165 (2) |
Symmetry code: (i) −x+1/2, y+1/2, z. |
Acknowledgements
MT and JK thank the Grant Agency of the Slovak Republic (grant No. 1/2449/05).
References
Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
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In the present work, the structure of N-(3,4-dimethylphenyl)-benzamide (N34DMPBA) has been determined to explore the effect of substituents on the structure of N-aromatic amides (Gowda et al., 2003; Gowda, Sowmya et al., 2007; Gowda, Foro & Fuess, 2007). The conformation of the N—H bond in N34DMPBA (FIg. 1) is anti to the meta methyl substituent in the aniline phenyl ring, similar to that observed with respect to the meta chloro substituent in N-(3,4-dichlorophenyl)-benzamide (N34DCPBA) (Gowda, Sowmya et al., 2007), but in contrast to the syn conformation observed with respect to the meta methyl substituent in the N-(3,4-dimethylphenyl)- acetamide (Gowda, Foro & Fuess, 2007). The bond parameters in N34DMPBA are similar to those in N34DCPBA and other benzanilides (Gowda et al., 2003). The molecules in N34DMPBA are packed into Column like s tructure in the direction of a axis through N—H···O hydrogen bonds (Table 1 & Fig. 2).