PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3359.
Published online 2010 November 30. doi:  10.1107/S1600536810049147
PMCID: PMC3011377

(2-Amino­phen­yl)(p-tol­yl)methanone

Abstract

In the title compound, C14H13NO, the two six-membered rings make a dihedral angle of 52.8 (3)°. An intra­molecular N—H(...)O hydrogen bond involving an amine H atom and the adjacent carbonyl O atom occurs. In the crystal, N—H(...)O and C—H(...)N inter­molecular hydrogen bonds are observed, which may be effective in stabilizing the structure.

Related literature

For the uses of 5-nitro­thio­phene-2-carb­oxy­lic acid, see: Shetty et al. (1999 [triangle]). For the synthesis of the title compound, see: Zhu et al. (2005 [triangle]). For standard bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3359-scheme1.jpg

Experimental

Crystal data

  • C14H13NO
  • M r = 211.25
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3359-efi1.jpg
  • a = 7.7720 (16) Å
  • b = 10.490 (2) Å
  • c = 14.114 (3) Å
  • V = 1150.7 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.977, T max = 0.992
  • 2387 measured reflections
  • 1241 independent reflections
  • 984 reflections with I > 2σ(I)
  • R int = 0.023
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.114
  • S = 1.01
  • 1241 reflections
  • 154 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.12 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810049147/su2231sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049147/su2231Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

supplementary crystallographic information

Comment

(2-Aminophenyl)(p-tolyl)methanone and its derivitives are important monomers, being utilized to synthesize oligomers containing a quinoline unit (Shetty et al., 1999). We report herein on the crystal structure of the title compound, (2-Aminophenyl)(p-tolyl)methanone.

In the title molecule (Fig. 1) the bond lengths (Allen et al., 1987) and angles are within normal ranges. An amine H-atom and the adjacent carbonyl O-atom forms an intramolecular N-H···O hydrogen bond (Fig. 1, Table 1). The two aromatic rings are planar, with a dihedral angle of 52.8 (3)°.

In the crystal, N-H···O and C—H···N intermolecular hydrogen bonds are observed, which stabilize the crystal structure (Fig. 2, Table 1).

Experimental

(2-Aminophenyl)(p-tolyl)methanone was prepared by the method reported in the literature (Zhu et al., 2005). Single crystals were obtained by dissolving (2-aminophenyl)(p-tolyl)methanone (0.5 g, 2.37 mmol) in ethyl acetate (50 ml) and evaporating the solvent slowly at room temperature for about 10 d.

Refinement

In the final cycles of refinement, in the absence of significant anomalous scattering effects, Friedel pairs were merged and Δf " set to zero. After checking their presence in a difference map, the NH2 H-atoms were freely refined. The C-bound H-atoms were positioned geometrically [C—H = 0.93 Å] and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level [The intermolecular N-H···O hydrogen bond is shown as a dashed line - Table 1].
Fig. 2.
Crystal packing of the title compound viewed along the c-axis [The hydrogen bonds are shown as dashed lines; details are given in Table 1].

Crystal data

C14H13NOF(000) = 448
Mr = 211.25Dx = 1.219 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 7.7720 (16) Åθ = 9–14°
b = 10.490 (2) ŵ = 0.08 mm1
c = 14.114 (3) ÅT = 298 K
V = 1150.7 (4) Å3Plate, brown
Z = 40.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer984 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
graphiteθmax = 25.4°, θmin = 2.4°
ω/2θ scansh = 0→9
Absorption correction: ψ scan (North et al., 1968)k = 0→12
Tmin = 0.977, Tmax = 0.992l = −17→17
2387 measured reflections3 standard reflections every 200 reflections
1241 independent reflections intensity decay: 1%

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114w = 1/[σ2(Fo2) + (0.077P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
1241 reflectionsΔρmax = 0.15 e Å3
154 parametersΔρmin = −0.12 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.029 (5)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles
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)

xyzUiso*/Ueq
O1−0.0723 (5)0.48772 (18)0.66689 (13)0.1072 (11)
N10.0516 (5)0.2583 (3)0.72595 (18)0.0903 (13)
C1−0.0893 (6)0.8175 (3)0.2825 (2)0.0979 (14)
C2−0.0848 (4)0.7203 (2)0.36079 (19)0.0649 (10)
C3−0.1864 (4)0.7310 (2)0.4405 (2)0.0668 (10)
C4−0.1798 (4)0.6431 (2)0.51329 (19)0.0611 (8)
C5−0.0737 (3)0.5373 (2)0.50607 (16)0.0507 (8)
C60.0293 (3)0.5256 (2)0.42633 (17)0.0562 (8)
C70.0251 (4)0.6161 (2)0.35603 (17)0.0612 (9)
C8−0.0684 (4)0.4450 (2)0.58631 (17)0.0626 (9)
C9−0.0553 (3)0.3074 (2)0.56775 (17)0.0515 (8)
C100.0012 (4)0.2205 (3)0.63780 (18)0.0597 (9)
C110.0141 (4)0.0914 (3)0.6133 (2)0.0665 (10)
C12−0.0327 (4)0.0487 (2)0.5261 (2)0.0670 (10)
C13−0.0940 (4)0.1319 (2)0.45806 (19)0.0632 (9)
C14−0.1042 (3)0.2588 (3)0.47965 (16)0.0548 (8)
H0B0.065 (5)0.203 (3)0.766 (2)0.094 (12)*
H1A−0.171400.882700.297800.1470*
H1B−0.121900.776900.224300.1470*
H1C0.022600.855100.275500.1470*
H0A0.029 (5)0.336 (3)0.743 (2)0.082 (11)*
H3A−0.261800.799500.445400.0800*
H4A−0.246600.655000.567200.0730*
H6A0.102100.455700.420400.0670*
H7A0.097500.607300.304000.0730*
H11A0.055700.033600.657700.0800*
H12A−0.02340−0.037600.512000.0800*
H13A−0.127500.102300.398800.0760*
H14A−0.145300.314900.433900.0660*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.203 (3)0.0665 (13)0.0521 (10)0.0088 (18)−0.0032 (16)−0.0151 (10)
N10.135 (3)0.079 (2)0.0570 (15)−0.006 (2)−0.0174 (16)0.0122 (15)
C10.139 (3)0.0648 (19)0.090 (2)−0.001 (2)−0.013 (2)0.0186 (16)
C20.0806 (19)0.0466 (14)0.0675 (16)−0.0038 (15)−0.0133 (16)−0.0008 (13)
C30.0709 (17)0.0412 (13)0.0882 (19)0.0067 (13)−0.0089 (17)−0.0106 (14)
C40.0668 (16)0.0459 (13)0.0706 (15)−0.0026 (13)0.0056 (14)−0.0141 (13)
C50.0588 (15)0.0404 (12)0.0529 (13)−0.0011 (11)−0.0032 (12)−0.0103 (10)
C60.0600 (15)0.0458 (13)0.0627 (14)0.0027 (13)−0.0049 (13)−0.0089 (12)
C70.0746 (18)0.0525 (14)0.0566 (13)−0.0028 (15)0.0018 (14)−0.0057 (12)
C80.082 (2)0.0539 (15)0.0518 (13)−0.0015 (15)−0.0025 (15)−0.0097 (12)
C90.0549 (15)0.0481 (13)0.0515 (13)−0.0006 (12)0.0029 (12)−0.0006 (11)
C100.0597 (16)0.0637 (15)0.0556 (14)−0.0069 (14)0.0048 (13)0.0089 (13)
C110.0647 (17)0.0523 (15)0.0824 (18)−0.0020 (14)0.0066 (16)0.0188 (14)
C120.0675 (18)0.0423 (13)0.0912 (19)−0.0034 (13)0.0102 (16)−0.0006 (14)
C130.0690 (17)0.0505 (14)0.0700 (16)−0.0059 (14)−0.0022 (15)−0.0095 (13)
C140.0588 (15)0.0487 (12)0.0570 (15)−0.0003 (12)−0.0055 (12)−0.0020 (12)

Geometric parameters (Å, °)

O1—C81.223 (3)C10—C111.401 (4)
N1—C101.363 (4)C11—C121.359 (4)
N1—H0B0.82 (3)C12—C131.382 (4)
N1—H0A0.87 (3)C13—C141.368 (4)
C1—C21.504 (4)C1—H1A0.9600
C2—C31.379 (4)C1—H1B0.9600
C2—C71.389 (4)C1—H1C0.9600
C3—C41.381 (4)C3—H3A0.9300
C4—C51.386 (3)C4—H4A0.9300
C5—C61.387 (3)C6—H6A0.9300
C5—C81.491 (3)C7—H7A0.9300
C6—C71.374 (3)C11—H11A0.9300
C8—C91.471 (3)C12—H12A0.9300
C9—C141.397 (3)C13—H13A0.9300
C9—C101.415 (4)C14—H14A0.9300
H0B—N1—H0A120 (3)C12—C13—C14118.7 (2)
C10—N1—H0B118 (2)C9—C14—C13122.5 (2)
C10—N1—H0A118 (2)C2—C1—H1A109.00
C1—C2—C3122.1 (2)C2—C1—H1B110.00
C1—C2—C7120.8 (3)C2—C1—H1C109.00
C3—C2—C7117.1 (2)H1A—C1—H1B109.00
C2—C3—C4122.1 (2)H1A—C1—H1C109.00
C3—C4—C5120.1 (3)H1B—C1—H1C109.00
C4—C5—C6118.3 (2)C2—C3—H3A119.00
C4—C5—C8118.7 (2)C4—C3—H3A119.00
C6—C5—C8122.9 (2)C3—C4—H4A120.00
C5—C6—C7120.8 (2)C5—C4—H4A120.00
C2—C7—C6121.6 (2)C5—C6—H6A120.00
C5—C8—C9120.3 (2)C7—C6—H6A120.00
O1—C8—C9121.8 (2)C2—C7—H7A119.00
O1—C8—C5117.9 (2)C6—C7—H7A119.00
C8—C9—C10122.0 (2)C10—C11—H11A119.00
C8—C9—C14119.9 (2)C12—C11—H11A119.00
C10—C9—C14118.1 (2)C11—C12—H12A120.00
C9—C10—C11118.2 (2)C13—C12—H12A120.00
N1—C10—C9122.7 (3)C12—C13—H13A121.00
N1—C10—C11119.1 (3)C14—C13—H13A121.00
C10—C11—C12121.5 (3)C9—C14—H14A119.00
C11—C12—C13120.9 (2)C13—C14—H14A119.00
C1—C2—C3—C4−178.7 (3)O1—C8—C9—C14160.0 (3)
C7—C2—C3—C40.4 (4)C5—C8—C9—C10160.6 (3)
C1—C2—C7—C6−179.2 (3)C5—C8—C9—C14−21.2 (4)
C3—C2—C7—C61.7 (4)C8—C9—C10—N1−1.8 (4)
C2—C3—C4—C5−2.6 (4)C8—C9—C10—C11−178.4 (3)
C3—C4—C5—C62.6 (4)C14—C9—C10—N1−180.0 (3)
C3—C4—C5—C8179.4 (2)C14—C9—C10—C113.5 (4)
C4—C5—C6—C7−0.5 (4)C8—C9—C14—C13179.6 (3)
C8—C5—C6—C7−177.2 (2)C10—C9—C14—C13−2.2 (4)
C4—C5—C8—O1−39.1 (4)N1—C10—C11—C12−179.3 (3)
C4—C5—C8—C9142.1 (3)C9—C10—C11—C12−2.7 (5)
C6—C5—C8—O1137.6 (3)C10—C11—C12—C130.4 (5)
C6—C5—C8—C9−41.2 (4)C11—C12—C13—C141.0 (5)
C5—C6—C7—C2−1.7 (4)C12—C13—C14—C9−0.1 (4)
O1—C8—C9—C10−18.1 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H0A···O10.87 (3)2.08 (3)2.723 (4)131 (3)
N1—H0B···O1i0.82 (3)2.45 (3)3.220 (4)158 (3)
C11—H11A···O1i0.932.533.319 (4)143

Symmetry codes: (i) −x, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2231).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shetty, A. S., Liu, E. B., Lachicotte, R. J. & Jenekhe, S. A. (1999). Chem. Mater.11, 2292–2295.
  • Zhu, H.-J., Wang, D.-D., Song, G.-L., Wang, J.-T. & Wang, K.-L. (2005). Acta Cryst. E61, o2209–o2210.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography