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organic compounds
1,2-Diphenyl-2-(m-tolylamino)ethanone1
aDepartamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo, C/ Julián Clavería, 8, 33006 Oviedo, Spain, and bDepartamento de Química, Facultad de Ciencias Naturales, Universidad de Oriente, Santiago de Cuba, Cuba
*Correspondence e-mail: sgg@uniovi.es
The title compound, C21H19NO, belongs to the family of α-aminoketones. The structure contains three benzene rings, two of which [the phenyl ring in the 1-position (B) and the methylaniline ring (A)] are nearly coplanar [dihedral angle = 5.4 (1)°], whereas the phenyl ring in the 2-position (C) is nearly normal to them [dihedral angles = 81.8 (1) and 87.0 (1)° for A/C and B/C, respectively]. The conformation of the N—H bond is syn to the C=O bond, favouring the formation of a centrosymmetric dimer of molecules in the The molecular packing is consolidated by this N—H⋯O hydrogen-bonding network.
Related literature
For the structure of alpha-aminoketones, see: Batsanov et al. (2006). For the of 1,2-diphenyl-2-(p-tolylamino)ethanone, see: Au & Tafeenko (1986
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell CrysAlis RED (Oxford Diffraction, 2008
); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1994
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997
); software used to prepare material for publication: WinGX (Farrugia, 1999
) and PLATON (Spek, 2009
).
Supporting information
https://doi.org/10.1107/S1600536810013371/su2170sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810013371/su2170Isup2.hkl
0.0235 mol benzoin, 0.0235 mol 3-methylaniline and 0.0235 mol boric acid were added to 10 ml of ethyleneglycol. The mixture was heated to reflux for 1 h, then 15 ml of ethanol were added and the mixture cooled to RT. The reaction was followed using TLC. The yellow precipitate obtained was washed with cold water and ethanol (yield 85%). Yellow needle-like crystals, suitable for x-ray
were obtained after a week by slow evaporation of a solution in ethanol.The NH H-atom was located in difference electron-density map and was freely refined: N-H = 0.858 (17) Å. The C-bound H-atoms were included in calculated positions and treated as riding atoms: C-H = 0.98 Å, 0.93 Å and 0.96 Å for tertiary CH, aromatic CH and CH3 H-atoms, respectively, with Uiso(H) = k × Ueq(C), where k = 1.2 for CH H-atoms, and 1.5 for CH3 H-atoms.
The structure of various members of the alpha-aminoketone family have been extensively studied (Batsanov et al., 2006). These compounds can be used as intermediates to synthesize other biologically active compounds like thiosemicarbazones. Alpha-aminoketones also exhibit biological activity but are less active than the thiosemicarbazones. They are generally synthesised by the reaction of an alpha-hydroxiketone with an amine.
The molecular structure of the title molecule is illustrated in Fig. 1. According to the dihedral angles between the benzene rings planes, two benzene rings are nearly coplanar whereas the central ring is almost normal to them (5.3 (1)° for A/B, 81.8 (1)° for A/C and 87.0 (1)° for B/C). Comparing these values with those in the similar structure where the methyl subtitutent is in the para position (5.1° for A/B, 86.28° for A/C and 84.19° for B/C), there are no noticeable differences (Au & Tafeenko, 1986).
In the ═O and N—H bonds into a syn orientation. The intermolecular distance between the centroids of the parallel benzene rings is ca. 3.77 Å. This value suggests the absence of any relevant π-stacking interactions.
the molecular packing is made up of a network of weak hydrogen-bonding interactions (Fig. 2 & Table 1), favouring the formation of centrosymmetric dimers. Such conformations bring the CFor the structure of alpha-aminoketones, see: Batsanov et al. (2006). For the
of 1,2-diphenyl-2-(p-tolylamino)ethanone, see: Au & Tafeenko (1986).Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell
CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).C21H19NO | Z = 2 |
Mr = 301.37 | F(000) = 320 |
Triclinic, P1 | Dx = 1.242 Mg m−3 |
Hall symbol: -P 1 | Melting point: 385.14 K |
a = 6.0510 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 11.5745 (4) Å | Cell parameters from 4346 reflections |
c = 12.9458 (7) Å | θ = 3.8–66.7° |
α = 112.542 (5)° | µ = 0.59 mm−1 |
β = 97.396 (4)° | T = 293 K |
γ = 99.960 (4)° | Needle, yellow |
V = 805.62 (8) Å3 | 0.34 × 0.12 × 0.07 mm |
Oxford Diffraction Xcalibur Gemini S diffractometer | 2833 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 2174 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 16.0827 pixels mm-1 | θmax = 66.7°, θmin = 3.8° |
ω scans | h = −6→7 |
Absorption correction: part of the [cubic fit to sin(theta)/lambda - 24 parameters; Parkin et al. (1995)] | model (ΔF) k = −10→13 |
Tmin = 0.919, Tmax = 0.960 | l = −15→14 |
8027 measured reflections |
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)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.0863P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
2833 reflections | Δρmax = 0.25 e Å−3 |
213 parameters | Δρmin = −0.16 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: 0.0041 (11) |
C21H19NO | γ = 99.960 (4)° |
Mr = 301.37 | V = 805.62 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.0510 (3) Å | Cu Kα radiation |
b = 11.5745 (4) Å | µ = 0.59 mm−1 |
c = 12.9458 (7) Å | T = 293 K |
α = 112.542 (5)° | 0.34 × 0.12 × 0.07 mm |
β = 97.396 (4)° |
Oxford Diffraction Xcalibur Gemini S diffractometer | 2833 independent reflections |
Absorption correction: part of the refinement model (ΔF) [cubic fit to sin(theta)/lambda - 24 parameters; Parkin et al. (1995)] | 2174 reflections with I > 2σ(I) |
Tmin = 0.919, Tmax = 0.960 | Rint = 0.027 |
8027 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.137 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.25 e Å−3 |
2833 reflections | Δρmin = −0.16 e Å−3 |
213 parameters |
Experimental. 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 > 2sigma(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. |
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 | 0.52659 (18) | 0.50924 (11) | 0.14596 (9) | 0.0662 (4) | |
N1 | 0.1300 (2) | 0.38301 (13) | 0.00199 (11) | 0.0529 (4) | |
C1 | 0.6200 (3) | 0.63202 (19) | 0.38272 (15) | 0.0714 (6) | |
C2 | 0.6620 (4) | 0.6946 (2) | 0.50033 (17) | 0.0880 (8) | |
C3 | 0.4898 (4) | 0.6891 (2) | 0.55688 (17) | 0.0847 (8) | |
C4 | 0.2717 (4) | 0.6232 (2) | 0.49658 (17) | 0.0863 (8) | |
C5 | 0.2260 (3) | 0.56261 (18) | 0.37817 (15) | 0.0707 (6) | |
C6 | 0.4006 (3) | 0.56467 (14) | 0.31949 (13) | 0.0497 (5) | |
C7 | 0.3671 (2) | 0.49865 (14) | 0.19224 (13) | 0.0480 (5) | |
C8 | 0.1322 (2) | 0.41085 (13) | 0.12058 (12) | 0.0452 (4) | |
C9 | 0.0958 (2) | 0.28933 (13) | 0.14383 (11) | 0.0454 (4) | |
C10 | −0.0802 (3) | 0.25707 (16) | 0.19337 (14) | 0.0586 (5) | |
C11 | −0.1102 (3) | 0.14576 (19) | 0.21171 (17) | 0.0757 (7) | |
C12 | 0.0364 (4) | 0.06604 (19) | 0.18093 (18) | 0.0819 (7) | |
C13 | 0.2102 (3) | 0.09623 (17) | 0.13051 (17) | 0.0742 (7) | |
C14 | 0.2411 (3) | 0.20731 (15) | 0.11226 (14) | 0.0574 (5) | |
C15 | −0.0560 (2) | 0.30252 (13) | −0.08485 (12) | 0.0452 (4) | |
C16 | −0.2728 (3) | 0.26933 (15) | −0.06433 (14) | 0.0540 (5) | |
C17 | −0.4522 (3) | 0.18600 (16) | −0.15360 (14) | 0.0597 (6) | |
C18 | −0.4218 (3) | 0.13398 (16) | −0.26408 (15) | 0.0633 (6) | |
C19 | −0.2086 (3) | 0.16684 (16) | −0.28761 (14) | 0.0578 (5) | |
C20 | −0.0286 (3) | 0.25155 (14) | −0.19799 (13) | 0.0510 (5) | |
C21 | −0.1709 (4) | 0.1084 (2) | −0.40766 (16) | 0.0896 (8) | |
H1 | 0.74080 | 0.63510 | 0.34540 | 0.0860* | |
H2 | 0.81000 | 0.74100 | 0.54130 | 0.1060* | |
H3 | 0.52000 | 0.73000 | 0.63640 | 0.1020* | |
H4 | 0.15330 | 0.61900 | 0.53520 | 0.1040* | |
H5 | 0.07610 | 0.52010 | 0.33780 | 0.0850* | |
H8 | 0.01180 | 0.45580 | 0.14410 | 0.0540* | |
H10 | −0.17960 | 0.31080 | 0.21460 | 0.0700* | |
H11 | −0.22970 | 0.12480 | 0.24490 | 0.0910* | |
H12 | 0.01770 | −0.00810 | 0.19430 | 0.0980* | |
H13 | 0.30790 | 0.04160 | 0.10850 | 0.0890* | |
H14 | 0.36020 | 0.22730 | 0.07850 | 0.0690* | |
H16 | −0.29700 | 0.30340 | 0.00980 | 0.0650* | |
H17 | −0.59640 | 0.16470 | −0.13870 | 0.0720* | |
H18 | −0.54410 | 0.07680 | −0.32300 | 0.0760* | |
H20 | 0.11400 | 0.27500 | −0.21360 | 0.0610* | |
H21A | −0.31250 | 0.05270 | −0.45850 | 0.1340* | |
H21B | −0.05730 | 0.05940 | −0.40990 | 0.1340* | |
H21C | −0.11860 | 0.17570 | −0.43120 | 0.1340* | |
H22 | 0.262 (3) | 0.4037 (17) | −0.0130 (15) | 0.062 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0533 (7) | 0.0727 (8) | 0.0548 (7) | −0.0058 (6) | 0.0118 (5) | 0.0167 (6) |
N1 | 0.0473 (7) | 0.0602 (8) | 0.0438 (7) | 0.0004 (6) | 0.0051 (6) | 0.0207 (6) |
C1 | 0.0584 (10) | 0.0864 (13) | 0.0546 (10) | 0.0023 (9) | 0.0014 (8) | 0.0235 (9) |
C2 | 0.0714 (12) | 0.1108 (17) | 0.0540 (11) | −0.0008 (11) | −0.0099 (10) | 0.0220 (11) |
C3 | 0.1014 (16) | 0.0868 (14) | 0.0459 (10) | 0.0088 (12) | 0.0028 (10) | 0.0164 (10) |
C4 | 0.0896 (14) | 0.0886 (14) | 0.0559 (11) | 0.0028 (12) | 0.0230 (10) | 0.0096 (10) |
C5 | 0.0637 (10) | 0.0698 (11) | 0.0536 (10) | 0.0000 (9) | 0.0116 (8) | 0.0066 (9) |
C6 | 0.0528 (8) | 0.0442 (8) | 0.0467 (8) | 0.0051 (6) | 0.0043 (7) | 0.0180 (7) |
C7 | 0.0482 (8) | 0.0424 (8) | 0.0495 (9) | 0.0043 (6) | 0.0072 (7) | 0.0189 (7) |
C8 | 0.0449 (7) | 0.0435 (7) | 0.0419 (8) | 0.0067 (6) | 0.0063 (6) | 0.0148 (6) |
C9 | 0.0449 (7) | 0.0429 (8) | 0.0373 (7) | 0.0024 (6) | −0.0008 (6) | 0.0114 (6) |
C10 | 0.0547 (9) | 0.0597 (9) | 0.0553 (10) | 0.0018 (7) | 0.0080 (7) | 0.0239 (8) |
C11 | 0.0766 (12) | 0.0717 (12) | 0.0716 (13) | −0.0114 (10) | 0.0029 (10) | 0.0387 (10) |
C12 | 0.0939 (14) | 0.0551 (10) | 0.0810 (14) | −0.0101 (10) | −0.0212 (11) | 0.0360 (10) |
C13 | 0.0802 (12) | 0.0503 (10) | 0.0758 (12) | 0.0156 (9) | −0.0107 (10) | 0.0177 (9) |
C14 | 0.0583 (9) | 0.0513 (9) | 0.0527 (9) | 0.0100 (7) | 0.0032 (7) | 0.0152 (7) |
C15 | 0.0466 (8) | 0.0422 (7) | 0.0455 (8) | 0.0090 (6) | 0.0030 (6) | 0.0199 (6) |
C16 | 0.0487 (8) | 0.0590 (9) | 0.0502 (9) | 0.0106 (7) | 0.0078 (7) | 0.0202 (7) |
C17 | 0.0452 (8) | 0.0632 (10) | 0.0640 (11) | 0.0057 (7) | 0.0031 (7) | 0.0253 (9) |
C18 | 0.0583 (10) | 0.0554 (9) | 0.0591 (10) | 0.0013 (8) | −0.0093 (8) | 0.0178 (8) |
C19 | 0.0662 (10) | 0.0531 (9) | 0.0479 (9) | 0.0111 (7) | 0.0037 (7) | 0.0187 (7) |
C20 | 0.0531 (8) | 0.0517 (8) | 0.0481 (9) | 0.0092 (7) | 0.0085 (7) | 0.0230 (7) |
C21 | 0.0968 (15) | 0.0917 (15) | 0.0515 (11) | 0.0013 (12) | 0.0072 (10) | 0.0113 (10) |
O1—C7 | 1.2123 (18) | C17—C18 | 1.374 (2) |
N1—C8 | 1.4405 (19) | C18—C19 | 1.386 (3) |
N1—C15 | 1.3810 (19) | C19—C20 | 1.388 (2) |
N1—H22 | 0.862 (19) | C19—C21 | 1.505 (3) |
C1—C6 | 1.383 (3) | C1—H1 | 0.9300 |
C1—C2 | 1.378 (3) | C2—H2 | 0.9300 |
C2—C3 | 1.355 (3) | C3—H3 | 0.9300 |
C3—C4 | 1.365 (3) | C4—H4 | 0.9300 |
C4—C5 | 1.385 (3) | C5—H5 | 0.9300 |
C5—C6 | 1.381 (3) | C8—H8 | 0.9800 |
C6—C7 | 1.495 (2) | C10—H10 | 0.9300 |
C7—C8 | 1.534 (2) | C11—H11 | 0.9300 |
C8—C9 | 1.534 (2) | C12—H12 | 0.9300 |
C9—C14 | 1.388 (2) | C13—H13 | 0.9300 |
C9—C10 | 1.381 (2) | C14—H14 | 0.9300 |
C10—C11 | 1.383 (3) | C16—H16 | 0.9300 |
C11—C12 | 1.375 (3) | C17—H17 | 0.9300 |
C12—C13 | 1.371 (3) | C18—H18 | 0.9300 |
C13—C14 | 1.380 (3) | C20—H20 | 0.9300 |
C15—C20 | 1.398 (2) | C21—H21A | 0.9600 |
C15—C16 | 1.390 (2) | C21—H21B | 0.9600 |
C16—C17 | 1.380 (2) | C21—H21C | 0.9600 |
C8—N1—C15 | 122.36 (13) | C6—C1—H1 | 120.00 |
C8—N1—H22 | 115.3 (12) | C1—C2—H2 | 120.00 |
C15—N1—H22 | 120.7 (12) | C3—C2—H2 | 120.00 |
C2—C1—C6 | 120.89 (18) | C2—C3—H3 | 120.00 |
C1—C2—C3 | 120.6 (2) | C4—C3—H3 | 120.00 |
C2—C3—C4 | 119.66 (19) | C3—C4—H4 | 120.00 |
C3—C4—C5 | 120.3 (2) | C5—C4—H4 | 120.00 |
C4—C5—C6 | 120.71 (18) | C4—C5—H5 | 120.00 |
C1—C6—C7 | 118.15 (15) | C6—C5—H5 | 120.00 |
C1—C6—C5 | 117.76 (15) | N1—C8—H8 | 109.00 |
C5—C6—C7 | 124.08 (15) | C7—C8—H8 | 109.00 |
O1—C7—C8 | 119.84 (13) | C9—C8—H8 | 109.00 |
O1—C7—C6 | 120.53 (14) | C9—C10—H10 | 120.00 |
C6—C7—C8 | 119.55 (13) | C11—C10—H10 | 120.00 |
N1—C8—C9 | 112.77 (13) | C10—C11—H11 | 120.00 |
C7—C8—C9 | 107.94 (12) | C12—C11—H11 | 120.00 |
N1—C8—C7 | 108.31 (12) | C11—C12—H12 | 120.00 |
C10—C9—C14 | 118.55 (16) | C13—C12—H12 | 120.00 |
C8—C9—C10 | 122.18 (13) | C12—C13—H13 | 120.00 |
C8—C9—C14 | 119.26 (13) | C14—C13—H13 | 120.00 |
C9—C10—C11 | 120.72 (17) | C9—C14—H14 | 120.00 |
C10—C11—C12 | 120.06 (19) | C13—C14—H14 | 120.00 |
C11—C12—C13 | 119.8 (2) | C15—C16—H16 | 120.00 |
C12—C13—C14 | 120.36 (19) | C17—C16—H16 | 120.00 |
C9—C14—C13 | 120.52 (16) | C16—C17—H17 | 119.00 |
C16—C15—C20 | 117.97 (14) | C18—C17—H17 | 119.00 |
N1—C15—C16 | 122.36 (13) | C17—C18—H18 | 120.00 |
N1—C15—C20 | 119.68 (13) | C19—C18—H18 | 120.00 |
C15—C16—C17 | 120.25 (15) | C15—C20—H20 | 119.00 |
C16—C17—C18 | 121.25 (17) | C19—C20—H20 | 119.00 |
C17—C18—C19 | 119.89 (17) | C19—C21—H21A | 109.00 |
C18—C19—C20 | 118.88 (16) | C19—C21—H21B | 109.00 |
C18—C19—C21 | 120.58 (17) | C19—C21—H21C | 110.00 |
C20—C19—C21 | 120.51 (17) | H21A—C21—H21B | 109.00 |
C15—C20—C19 | 121.73 (16) | H21A—C21—H21C | 110.00 |
C2—C1—H1 | 120.00 | H21B—C21—H21C | 109.00 |
C15—N1—C8—C7 | 177.87 (14) | N1—C8—C9—C14 | 55.51 (17) |
C15—N1—C8—C9 | 58.48 (18) | C7—C8—C9—C10 | 117.19 (14) |
C8—N1—C15—C16 | 17.0 (2) | C7—C8—C9—C14 | −64.09 (16) |
C8—N1—C15—C20 | −162.92 (15) | C8—C9—C10—C11 | 179.09 (15) |
C6—C1—C2—C3 | 1.5 (4) | C14—C9—C10—C11 | 0.4 (2) |
C2—C1—C6—C5 | 0.1 (3) | C8—C9—C14—C13 | −178.99 (15) |
C2—C1—C6—C7 | −179.82 (19) | C10—C9—C14—C13 | −0.2 (2) |
C1—C2—C3—C4 | −1.4 (4) | C9—C10—C11—C12 | 0.2 (3) |
C2—C3—C4—C5 | −0.3 (4) | C10—C11—C12—C13 | −1.0 (3) |
C3—C4—C5—C6 | 1.9 (4) | C11—C12—C13—C14 | 1.1 (3) |
C4—C5—C6—C1 | −1.8 (3) | C12—C13—C14—C9 | −0.5 (3) |
C4—C5—C6—C7 | 178.17 (19) | N1—C15—C16—C17 | −178.40 (17) |
C1—C6—C7—O1 | −3.4 (3) | C20—C15—C16—C17 | 1.5 (3) |
C1—C6—C7—C8 | 173.22 (17) | N1—C15—C20—C19 | 177.80 (17) |
C5—C6—C7—O1 | 176.72 (18) | C16—C15—C20—C19 | −2.2 (3) |
C5—C6—C7—C8 | −6.7 (3) | C15—C16—C17—C18 | 0.1 (3) |
O1—C7—C8—N1 | −16.0 (2) | C16—C17—C18—C19 | −1.1 (3) |
O1—C7—C8—C9 | 106.37 (17) | C17—C18—C19—C20 | 0.5 (3) |
C6—C7—C8—N1 | 167.39 (14) | C17—C18—C19—C21 | 178.57 (19) |
C6—C7—C8—C9 | −70.22 (17) | C18—C19—C20—C15 | 1.1 (3) |
N1—C8—C9—C10 | −123.21 (14) | C21—C19—C20—C15 | −176.92 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H22···O1i | 0.859 (17) | 2.660 (17) | 3.3913 (17) | 143.8 (15) |
Symmetry code: (i) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C21H19NO |
Mr | 301.37 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 6.0510 (3), 11.5745 (4), 12.9458 (7) |
α, β, γ (°) | 112.542 (5), 97.396 (4), 99.960 (4) |
V (Å3) | 805.62 (8) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 0.59 |
Crystal size (mm) | 0.34 × 0.12 × 0.07 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Gemini S |
Absorption correction | Part of the refinement model (ΔF) [cubic fit to sin(theta)/lambda - 24 parameters; Parkin et al. (1995)] |
Tmin, Tmax | 0.919, 0.960 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8027, 2833, 2174 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.137, 1.09 |
No. of reflections | 2833 |
No. of parameters | 213 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.25, −0.16 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H22···O1i | 0.859 (17) | 2.660 (17) | 3.3913 (17) | 143.8 (15) |
Symmetry code: (i) −x+1, −y+1, −z. |
Footnotes
1Dedicated to the memory of Professor José Manuel Concellón.
Acknowledgements
Financial support by the Agencia Española de Cooperación Internacional y Desarrollo (AECID), FEDER funding, the Spanish MICINN (MAT2006–01997 and Factoría de Cristalización Consolider Ingenio 2010) and the Gobierno del Principado de Asturias (PCTI) is acknowledged. Special acknowledgements go to Professor José Manuel Concellón for his support and scientific advice.
References
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The structure of various members of the alpha-aminoketone family have been extensively studied (Batsanov et al., 2006). These compounds can be used as intermediates to synthesize other biologically active compounds like thiosemicarbazones. Alpha-aminoketones also exhibit biological activity but are less active than the thiosemicarbazones. They are generally synthesised by the reaction of an alpha-hydroxiketone with an amine.
The molecular structure of the title molecule is illustrated in Fig. 1. According to the dihedral angles between the benzene rings planes, two benzene rings are nearly coplanar whereas the central ring is almost normal to them (5.3 (1)° for A/B, 81.8 (1)° for A/C and 87.0 (1)° for B/C). Comparing these values with those in the similar structure where the methyl subtitutent is in the para position (5.1° for A/B, 86.28° for A/C and 84.19° for B/C), there are no noticeable differences (Au & Tafeenko, 1986).
In the crystal structure, the molecular packing is made up of a network of weak hydrogen-bonding interactions (Fig. 2 & Table 1), favouring the formation of centrosymmetric dimers. Such conformations bring the C═O and N—H bonds into a syn orientation. The intermolecular distance between the centroids of the parallel benzene rings is ca. 3.77 Å. This value suggests the absence of any relevant π-stacking interactions.