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ISSN: 2056-9890

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

(Received 11 December 2007; accepted 14 December 2007; online 21 December 2007)

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, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63. lw2051.]); Gowda et al. (2003[Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225-230.]); Gowda, Sowmya et al. (2007[Gowda, B. T., Sowmya, B. P., Tokarčík, M., Kožíšek, J. & Fuess, H. (2007). Acta Cryst. E63, o3365.]).

[Scheme 1]

Experimental

Crystal data
  • C15H15NO

  • Mr = 225.28

  • Orthorhombic, P b c a

  • a = 9.1082 (2) Å

  • b = 9.8123 (2) Å

  • c = 28.5126 (8) Å

  • V = 2548.24 (10) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 295 (2) K

  • 0.33 × 0.11 × 0.08 mm

Data collection
  • Oxford Diffraction Xcalibur System diffractometer

  • Absorption correction: none

  • 21605 measured reflections

  • 2527 independent reflections

  • 1448 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.194

  • S = 0.97

  • 2527 reflections

  • 159 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O1i 0.84 (2) 2.12 (2) 2.948 (2) 165 (2)
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].

Data collection: CrysAlis CCD (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2002[Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]) and WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

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).

Related literature top

For related literature, see: Gowda, Foro & Fuess (2007); Gowda et al. (2003); Gowda, Sowmya et al. (2007).

Experimental top

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.

Refinement top

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 refinement 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).

Structure description top

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).

For related literature, see: Gowda, Foro & Fuess (2007); Gowda et al. (2003); Gowda, Sowmya et al. (2007).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Part of crystal structure of the title compound showing the hydrogen bonds N1–H1N···O1(i). Symmetry code (i): -x + 1/2, y + 1/2, z.
N-(3,4-Dimethylphenyl)benzamide top
Crystal data top
C15H15NOF(000) = 960
Mr = 225.28Dx = 1.174 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 6829 reflections
a = 9.1082 (2) Åθ = 3.0–29.5°
b = 9.8123 (2) ŵ = 0.07 mm1
c = 28.5126 (8) ÅT = 295 K
V = 2548.24 (10) Å3Prism, colourless
Z = 80.33 × 0.11 × 0.08 mm
Data collection top
Oxford Diffraction Xcalibur System
diffractometer
1448 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.035
Graphite monochromatorθmax = 26.2°, θmin = 5.1°
Detector resolution: 10.4340 pixels mm-1h = 119
ω scans with κ offsetsk = 1212
21605 measured reflectionsl = 3235
2527 independent reflections
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194H 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 parametersΔρmax = 0.37 e Å3
3 restraintsΔρmin = 0.19 e Å3
Crystal data top
C15H15NOV = 2548.24 (10) Å3
Mr = 225.28Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 9.1082 (2) ŵ = 0.07 mm1
b = 9.8123 (2) ÅT = 295 K
c = 28.5126 (8) Å0.33 × 0.11 × 0.08 mm
Data collection top
Oxford Diffraction Xcalibur System
diffractometer
1448 reflections with I > 2σ(I)
21605 measured reflectionsRint = 0.035
2527 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0583 restraints
wR(F2) = 0.194H atoms treated by a mixture of independent and constrained refinement
S = 0.97Δρmax = 0.37 e Å3
2527 reflectionsΔρmin = 0.19 e Å3
159 parameters
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
C10.1683 (2)0.51852 (17)0.15178 (7)0.0543 (5)
C20.04493 (19)0.58368 (18)0.17772 (7)0.0526 (5)
C30.0315 (2)0.5050 (2)0.21000 (8)0.0651 (6)
H30.00630.41390.21410.078*
C40.1439 (3)0.5599 (2)0.23587 (9)0.0762 (7)
H40.19310.50680.25780.091*
C50.1835 (3)0.6937 (2)0.22926 (9)0.0766 (7)
H50.26020.73070.24660.092*
C60.1109 (2)0.7724 (2)0.19736 (9)0.0724 (7)
H60.13840.86270.19290.087*
C70.0038 (2)0.71760 (19)0.17159 (8)0.0608 (6)
H70.05340.77170.15000.073*
C80.4041 (2)0.55741 (19)0.11157 (8)0.0631 (6)
C90.4082 (3)0.4574 (2)0.07867 (8)0.0728 (7)
H90.32090.41710.06900.087*
C100.5432 (3)0.4126 (2)0.05859 (8)0.0762 (7)
C110.6702 (3)0.4749 (2)0.07412 (9)0.0804 (7)
C120.6653 (3)0.5762 (3)0.10680 (10)0.0874 (8)
H120.75200.61750.11650.105*
C130.5336 (2)0.6185 (3)0.12574 (10)0.0751 (7)
H130.53190.68780.14800.090*
C140.8200 (4)0.4325 (3)0.05424 (14)0.1195 (12)
H14A0.89430.49390.06550.179*
H14B0.81690.43580.02060.179*
H14C0.84260.34150.06420.179*
C150.5398 (4)0.3011 (3)0.02331 (12)0.1179 (11)
H15A0.61760.31420.00100.177*
H15B0.44710.30200.00730.177*
H15C0.55250.21500.03880.177*
N10.26924 (19)0.60131 (17)0.13237 (7)0.0614 (5)
H1N0.268 (2)0.685 (2)0.1389 (8)0.074*
O10.17788 (16)0.39356 (13)0.14930 (6)0.0777 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0539 (11)0.0379 (10)0.0710 (13)0.0013 (8)0.0095 (9)0.0014 (8)
C20.0473 (11)0.0428 (11)0.0677 (13)0.0043 (7)0.0114 (9)0.0008 (8)
C30.0660 (14)0.0438 (11)0.0854 (15)0.0053 (9)0.0009 (11)0.0047 (10)
C40.0789 (16)0.0630 (14)0.0869 (16)0.0100 (11)0.0189 (13)0.0031 (11)
C50.0701 (15)0.0670 (15)0.0927 (17)0.0000 (11)0.0149 (12)0.0082 (12)
C60.0709 (14)0.0501 (11)0.0963 (16)0.0082 (10)0.0072 (13)0.0006 (11)
C70.0604 (12)0.0439 (11)0.0781 (14)0.0018 (9)0.0001 (10)0.0058 (10)
C80.0752 (15)0.0450 (11)0.0692 (13)0.0032 (10)0.0047 (11)0.0064 (10)
C90.0859 (17)0.0577 (13)0.0748 (14)0.0017 (11)0.0030 (12)0.0058 (11)
C100.107 (2)0.0519 (13)0.0697 (15)0.0122 (12)0.0034 (13)0.0056 (11)
C110.0936 (19)0.0621 (14)0.0855 (16)0.0091 (12)0.0067 (14)0.0044 (12)
C120.0704 (16)0.0881 (17)0.1036 (19)0.0007 (13)0.0041 (14)0.0054 (15)
C130.0639 (14)0.0710 (15)0.0903 (17)0.0011 (11)0.0054 (12)0.0065 (12)
C140.106 (2)0.108 (2)0.145 (3)0.0300 (18)0.039 (2)0.0006 (19)
C150.174 (3)0.085 (2)0.095 (2)0.0096 (18)0.011 (2)0.0201 (16)
N10.0628 (11)0.0394 (9)0.0821 (12)0.0001 (8)0.0098 (9)0.0019 (8)
O10.0706 (10)0.0401 (9)0.1224 (14)0.0007 (6)0.0090 (9)0.0026 (8)
Geometric parameters (Å, º) top
C1—O11.231 (2)C9—C101.425 (4)
C1—N11.346 (2)C9—H90.9300
C1—C21.490 (3)C10—C111.382 (4)
C2—C71.377 (3)C10—C151.487 (4)
C2—C31.389 (3)C11—C121.363 (4)
C3—C41.372 (3)C11—C141.535 (4)
C3—H30.9300C12—C131.379 (4)
C4—C51.374 (3)C12—H120.9300
C4—H40.9300C13—H130.9300
C5—C61.364 (3)C14—H14A0.9600
C5—H50.9300C14—H14B0.9600
C6—C71.386 (3)C14—H14C0.9600
C6—H60.9300C15—H15A0.9600
C7—H70.9300C15—H15B0.9600
C8—C91.358 (3)C15—H15C0.9600
C8—C131.384 (3)N1—H1N0.84 (2)
C8—N11.430 (3)
O1—C1—N1121.96 (18)C11—C10—C9117.2 (2)
O1—C1—C2120.61 (17)C11—C10—C15124.1 (3)
N1—C1—C2117.41 (15)C9—C10—C15118.7 (3)
C7—C2—C3118.57 (18)C12—C11—C10120.9 (2)
C7—C2—C1123.48 (17)C12—C11—C14118.6 (3)
C3—C2—C1117.95 (16)C10—C11—C14120.4 (3)
C4—C3—C2120.78 (19)C11—C12—C13121.0 (2)
C4—C3—H3119.6C11—C12—H12119.5
C2—C3—H3119.6C13—C12—H12119.5
C3—C4—C5119.8 (2)C12—C13—C8119.8 (2)
C3—C4—H4120.1C12—C13—H13120.1
C5—C4—H4120.1C8—C13—H13120.1
C6—C5—C4120.3 (2)C11—C14—H14A109.5
C6—C5—H5119.8C11—C14—H14B109.5
C4—C5—H5119.8H14A—C14—H14B109.5
C5—C6—C7120.0 (2)C11—C14—H14C109.5
C5—C6—H6120.0H14A—C14—H14C109.5
C7—C6—H6120.0H14B—C14—H14C109.5
C2—C7—C6120.50 (19)C10—C15—H15A109.5
C2—C7—H7119.7C10—C15—H15B109.5
C6—C7—H7119.7H15A—C15—H15B109.5
C9—C8—C13119.4 (2)C10—C15—H15C109.5
C9—C8—N1121.9 (2)H15A—C15—H15C109.5
C13—C8—N1118.7 (2)H15B—C15—H15C109.5
C8—C9—C10121.6 (2)C1—N1—C8125.11 (16)
C8—C9—H9119.2C1—N1—H1N119.4 (16)
C10—C9—H9119.2C8—N1—H1N113.3 (16)
O1—C1—C2—C7161.5 (2)C8—C9—C10—C15179.0 (2)
N1—C1—C2—C719.9 (3)C9—C10—C11—C120.9 (4)
O1—C1—C2—C319.0 (3)C15—C10—C11—C12179.6 (2)
N1—C1—C2—C3159.59 (19)C9—C10—C11—C14180.0 (2)
C7—C2—C3—C41.2 (3)C15—C10—C11—C141.3 (4)
C1—C2—C3—C4178.3 (2)C10—C11—C12—C130.8 (4)
C2—C3—C4—C51.3 (4)C14—C11—C12—C13179.9 (3)
C3—C4—C5—C60.5 (4)C11—C12—C13—C80.1 (4)
C4—C5—C6—C70.3 (4)C9—C8—C13—C120.7 (3)
C3—C2—C7—C60.4 (3)N1—C8—C13—C12178.9 (2)
C1—C2—C7—C6179.1 (2)O1—C1—N1—C87.0 (3)
C5—C6—C7—C20.3 (3)C2—C1—N1—C8171.52 (18)
C13—C8—C9—C100.6 (3)C9—C8—N1—C151.0 (3)
N1—C8—C9—C10179.02 (19)C13—C8—N1—C1128.6 (2)
C8—C9—C10—C110.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.84 (2)2.12 (2)2.948 (2)165 (2)
Symmetry code: (i) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC15H15NO
Mr225.28
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)295
a, b, c (Å)9.1082 (2), 9.8123 (2), 28.5126 (8)
V3)2548.24 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.33 × 0.11 × 0.08
Data collection
DiffractometerOxford Diffraction Xcalibur System
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
21605, 2527, 1448
Rint0.035
(sin θ/λ)max1)0.621
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.194, 0.97
No. of reflections2527
No. of parameters159
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.84 (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

First citationBrandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationGowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63. lw2051.  Google Scholar
First citationGowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230.  CAS Google Scholar
First citationGowda, B. T., Sowmya, B. P., Tokarčík, M., Kožíšek, J. & Fuess, H. (2007). Acta Cryst. E63, o3365.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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