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organic compounds
(2-Aminophenyl)(p-tolyl)methanone
aSchool of Bio-chemistry and Environmental Engineering, Nanjing Xiaozhuang University, 3601 Hongjing Road, Jiangning District, Nanjing 211171, People's Republic of China, and bDepartment of Chemical Engineering, Nanjing College of Chemical Technology, No 625, Geguan Road, Luhe, Nanjing 210048, People's Republic of China
*Correspondence e-mail: zdlocean@yahoo.com.cn
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). For the synthesis of the title compound, see: Zhu et al. (2005
). For standard bond-length data, see: Allen et al. (1987
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995
); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: SHELXTL (Sheldrick, 2008
); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536810049147/su2231sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810049147/su2231Isup2.hkl
(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.
In the final cycles of
in the absence of significant 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).(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
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
(Fig. 2, Table 1).For the uses of 5-nitrothiophene-2-carboxylic acid, see: Shetty et al. (1999). For the synthesis of the title compound, see: Zhu et al. (2005). For standard bond-length data, see: Allen et al. (1987).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C14H13NO | F(000) = 448 |
Mr = 211.25 | Dx = 1.219 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 7.7720 (16) Å | θ = 9–14° |
b = 10.490 (2) Å | µ = 0.08 mm−1 |
c = 14.114 (3) Å | T = 298 K |
V = 1150.7 (4) Å3 | Plate, brown |
Z = 4 | 0.30 × 0.20 × 0.10 mm |
Enraf–Nonius CAD-4 diffractometer | 984 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 25.4°, θmin = 2.4° |
ω/2θ scans | h = 0→9 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→12 |
Tmin = 0.977, Tmax = 0.992 | l = −17→17 |
2387 measured reflections | 3 standard reflections every 200 reflections |
1241 independent reflections | intensity decay: 1% |
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)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.077P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
1241 reflections | Δρmax = 0.15 e Å−3 |
154 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.029 (5) |
C14H13NO | V = 1150.7 (4) Å3 |
Mr = 211.25 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.7720 (16) Å | µ = 0.08 mm−1 |
b = 10.490 (2) Å | T = 298 K |
c = 14.114 (3) Å | 0.30 × 0.20 × 0.10 mm |
Enraf–Nonius CAD-4 diffractometer | 984 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.023 |
Tmin = 0.977, Tmax = 0.992 | 3 standard reflections every 200 reflections |
2387 measured reflections | intensity decay: 1% |
1241 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.15 e Å−3 |
1241 reflections | Δρmin = −0.12 e Å−3 |
154 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.0723 (5) | 0.48772 (18) | 0.66689 (13) | 0.1072 (11) | |
N1 | 0.0516 (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) | |
C6 | 0.0293 (3) | 0.5256 (2) | 0.42633 (17) | 0.0562 (8) | |
C7 | 0.0251 (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) | |
C10 | 0.0012 (4) | 0.2205 (3) | 0.63780 (18) | 0.0597 (9) | |
C11 | 0.0141 (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) | |
H0B | 0.065 (5) | 0.203 (3) | 0.766 (2) | 0.094 (12)* | |
H1A | −0.17140 | 0.88270 | 0.29780 | 0.1470* | |
H1B | −0.12190 | 0.77690 | 0.22430 | 0.1470* | |
H1C | 0.02260 | 0.85510 | 0.27550 | 0.1470* | |
H0A | 0.029 (5) | 0.336 (3) | 0.743 (2) | 0.082 (11)* | |
H3A | −0.26180 | 0.79950 | 0.44540 | 0.0800* | |
H4A | −0.24660 | 0.65500 | 0.56720 | 0.0730* | |
H6A | 0.10210 | 0.45570 | 0.42040 | 0.0670* | |
H7A | 0.09750 | 0.60730 | 0.30400 | 0.0730* | |
H11A | 0.05570 | 0.03360 | 0.65770 | 0.0800* | |
H12A | −0.02340 | −0.03760 | 0.51200 | 0.0800* | |
H13A | −0.12750 | 0.10230 | 0.39880 | 0.0760* | |
H14A | −0.14530 | 0.31490 | 0.43390 | 0.0660* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.203 (3) | 0.0665 (13) | 0.0521 (10) | 0.0088 (18) | −0.0032 (16) | −0.0151 (10) |
N1 | 0.135 (3) | 0.079 (2) | 0.0570 (15) | −0.006 (2) | −0.0174 (16) | 0.0122 (15) |
C1 | 0.139 (3) | 0.0648 (19) | 0.090 (2) | −0.001 (2) | −0.013 (2) | 0.0186 (16) |
C2 | 0.0806 (19) | 0.0466 (14) | 0.0675 (16) | −0.0038 (15) | −0.0133 (16) | −0.0008 (13) |
C3 | 0.0709 (17) | 0.0412 (13) | 0.0882 (19) | 0.0067 (13) | −0.0089 (17) | −0.0106 (14) |
C4 | 0.0668 (16) | 0.0459 (13) | 0.0706 (15) | −0.0026 (13) | 0.0056 (14) | −0.0141 (13) |
C5 | 0.0588 (15) | 0.0404 (12) | 0.0529 (13) | −0.0011 (11) | −0.0032 (12) | −0.0103 (10) |
C6 | 0.0600 (15) | 0.0458 (13) | 0.0627 (14) | 0.0027 (13) | −0.0049 (13) | −0.0089 (12) |
C7 | 0.0746 (18) | 0.0525 (14) | 0.0566 (13) | −0.0028 (15) | 0.0018 (14) | −0.0057 (12) |
C8 | 0.082 (2) | 0.0539 (15) | 0.0518 (13) | −0.0015 (15) | −0.0025 (15) | −0.0097 (12) |
C9 | 0.0549 (15) | 0.0481 (13) | 0.0515 (13) | −0.0006 (12) | 0.0029 (12) | −0.0006 (11) |
C10 | 0.0597 (16) | 0.0637 (15) | 0.0556 (14) | −0.0069 (14) | 0.0048 (13) | 0.0089 (13) |
C11 | 0.0647 (17) | 0.0523 (15) | 0.0824 (18) | −0.0020 (14) | 0.0066 (16) | 0.0188 (14) |
C12 | 0.0675 (18) | 0.0423 (13) | 0.0912 (19) | −0.0034 (13) | 0.0102 (16) | −0.0006 (14) |
C13 | 0.0690 (17) | 0.0505 (14) | 0.0700 (16) | −0.0059 (14) | −0.0022 (15) | −0.0095 (13) |
C14 | 0.0588 (15) | 0.0487 (12) | 0.0570 (15) | −0.0003 (12) | −0.0055 (12) | −0.0020 (12) |
O1—C8 | 1.223 (3) | C10—C11 | 1.401 (4) |
N1—C10 | 1.363 (4) | C11—C12 | 1.359 (4) |
N1—H0B | 0.82 (3) | C12—C13 | 1.382 (4) |
N1—H0A | 0.87 (3) | C13—C14 | 1.368 (4) |
C1—C2 | 1.504 (4) | C1—H1A | 0.9600 |
C2—C3 | 1.379 (4) | C1—H1B | 0.9600 |
C2—C7 | 1.389 (4) | C1—H1C | 0.9600 |
C3—C4 | 1.381 (4) | C3—H3A | 0.9300 |
C4—C5 | 1.386 (3) | C4—H4A | 0.9300 |
C5—C6 | 1.387 (3) | C6—H6A | 0.9300 |
C5—C8 | 1.491 (3) | C7—H7A | 0.9300 |
C6—C7 | 1.374 (3) | C11—H11A | 0.9300 |
C8—C9 | 1.471 (3) | C12—H12A | 0.9300 |
C9—C14 | 1.397 (3) | C13—H13A | 0.9300 |
C9—C10 | 1.415 (4) | C14—H14A | 0.9300 |
H0B—N1—H0A | 120 (3) | C12—C13—C14 | 118.7 (2) |
C10—N1—H0B | 118 (2) | C9—C14—C13 | 122.5 (2) |
C10—N1—H0A | 118 (2) | C2—C1—H1A | 109.00 |
C1—C2—C3 | 122.1 (2) | C2—C1—H1B | 110.00 |
C1—C2—C7 | 120.8 (3) | C2—C1—H1C | 109.00 |
C3—C2—C7 | 117.1 (2) | H1A—C1—H1B | 109.00 |
C2—C3—C4 | 122.1 (2) | H1A—C1—H1C | 109.00 |
C3—C4—C5 | 120.1 (3) | H1B—C1—H1C | 109.00 |
C4—C5—C6 | 118.3 (2) | C2—C3—H3A | 119.00 |
C4—C5—C8 | 118.7 (2) | C4—C3—H3A | 119.00 |
C6—C5—C8 | 122.9 (2) | C3—C4—H4A | 120.00 |
C5—C6—C7 | 120.8 (2) | C5—C4—H4A | 120.00 |
C2—C7—C6 | 121.6 (2) | C5—C6—H6A | 120.00 |
C5—C8—C9 | 120.3 (2) | C7—C6—H6A | 120.00 |
O1—C8—C9 | 121.8 (2) | C2—C7—H7A | 119.00 |
O1—C8—C5 | 117.9 (2) | C6—C7—H7A | 119.00 |
C8—C9—C10 | 122.0 (2) | C10—C11—H11A | 119.00 |
C8—C9—C14 | 119.9 (2) | C12—C11—H11A | 119.00 |
C10—C9—C14 | 118.1 (2) | C11—C12—H12A | 120.00 |
C9—C10—C11 | 118.2 (2) | C13—C12—H12A | 120.00 |
N1—C10—C9 | 122.7 (3) | C12—C13—H13A | 121.00 |
N1—C10—C11 | 119.1 (3) | C14—C13—H13A | 121.00 |
C10—C11—C12 | 121.5 (3) | C9—C14—H14A | 119.00 |
C11—C12—C13 | 120.9 (2) | C13—C14—H14A | 119.00 |
C1—C2—C3—C4 | −178.7 (3) | O1—C8—C9—C14 | 160.0 (3) |
C7—C2—C3—C4 | 0.4 (4) | C5—C8—C9—C10 | 160.6 (3) |
C1—C2—C7—C6 | −179.2 (3) | C5—C8—C9—C14 | −21.2 (4) |
C3—C2—C7—C6 | 1.7 (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—C6 | 2.6 (4) | C14—C9—C10—N1 | −180.0 (3) |
C3—C4—C5—C8 | 179.4 (2) | C14—C9—C10—C11 | 3.5 (4) |
C4—C5—C6—C7 | −0.5 (4) | C8—C9—C14—C13 | 179.6 (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—C9 | 142.1 (3) | C9—C10—C11—C12 | −2.7 (5) |
C6—C5—C8—O1 | 137.6 (3) | C10—C11—C12—C13 | 0.4 (5) |
C6—C5—C8—C9 | −41.2 (4) | C11—C12—C13—C14 | 1.0 (5) |
C5—C6—C7—C2 | −1.7 (4) | C12—C13—C14—C9 | −0.1 (4) |
O1—C8—C9—C10 | −18.1 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H0A···O1 | 0.87 (3) | 2.08 (3) | 2.723 (4) | 131 (3) |
N1—H0B···O1i | 0.82 (3) | 2.45 (3) | 3.220 (4) | 158 (3) |
C11—H11A···O1i | 0.93 | 2.53 | 3.319 (4) | 143 |
Symmetry code: (i) −x, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C14H13NO |
Mr | 211.25 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 298 |
a, b, c (Å) | 7.7720 (16), 10.490 (2), 14.114 (3) |
V (Å3) | 1150.7 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.977, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2387, 1241, 984 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.603 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.114, 1.01 |
No. of reflections | 1241 |
No. of parameters | 154 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.15, −0.12 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H0A···O1 | 0.87 (3) | 2.08 (3) | 2.723 (4) | 131 (3) |
N1—H0B···O1i | 0.82 (3) | 2.45 (3) | 3.220 (4) | 158 (3) |
C11—H11A···O1i | 0.93 | 2.53 | 3.319 (4) | 143 |
Symmetry code: (i) −x, y−1/2, −z+3/2. |
Acknowledgements
The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.
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. CSD CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
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(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).