organic compounds
2-[(Anilino)(2-nitrophenyl)methyl]cyclohexanone
aDepartment of Chemistry, University of Maragheh, Maragheh, Iran, and bDepartment of Physics, Ondokuz Mayis University, TR-55139 Samsun, Turkey
*Correspondence e-mail: eftekharisis@maragheh.ac.ir
In the title compound, C19H20N2O3, the cyclohexanone ring adopts a chair conformation with the aminomethyl group is positioned equatorially. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, molecules are linked by N—H⋯O hydrogen bonds.
Related literature
For the synthesis of the title compound and related compounds, see: Eftekhari-Sis et al. (2012a,b). For the biological activity of β-amino see: Arend et al. (1998). For the anti-inflammatory and antimicrobial activity of β-amino see: Jadhav et al. (2008) and Kalluraya et al. (2001), respectively. For information on the Mannich reaction, see: Eftekhari-Sis et al. (2006); Samet et al. (2009); Azizi et al. (2006); Cordova (2004). For related structures, see: Eftekhari-Sis et al. (2012b); Yuan et al. (2007); Fun et al. (2009).
Experimental
Crystal data
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Refinement
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Data collection: X-AREA (Stoe & Cie, 2002); cell X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2–8); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
https://doi.org/10.1107/S1600536812036859/fj2593sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812036859/fj2593Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812036859/fj2593Isup3.mol
Supporting information file. DOI: https://doi.org/10.1107/S1600536812036859/fj2593Isup4.cml
The title compound was obtained by adding of 0.04 g of Laponite-HMPC nano composite (Eftekhari-Sis et al., 2012a,b) to a mixture of 0.5 mmol of 2-nitrobenzaldehyde, 0.5 mmol of aniline and 3 equiv. of cyclohexanone and stirring at room temperature for 24 h. After completion of the reaction, 5 ml EtOH was added and catalyst was removed by filtration, and filtrate was concentrated under reduced pressure. The obtained crud product was recrystallized from EtOH to afford title compound in 62% yield. Colorless crystals suitable for
determination were grown from EtOH.Carbon bound H atoms were positioned geometrically, with C—H=0.93, 0.97, and 0.98 Å for aromatic, methylene and methine H, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C). The nitrogen H atoms were located from the difference Fourier map allowed to refine freely.
β-amino are widely found in natural and un-natural products, which exhibit anti-inflammatory (Jadhav et al., 2008) and antimicrobial (Kalluraya et al., 2001) activities. Mannich reaction (Eftekhari-Sis et al., 2006; Samet et al., 2009; Azizi et al., 2006; Cordova, 2004) is one of the most important basic reactions in organic chemistry for its use in synthesis of β-Amino We have synthesized the title compound and report its structure here, Fig 1. The cyclohexanone ring adopts chair conformation, and aminomethyl moiety is positioned equatorially on ring at C1.
For the synthesis of the title compound and related compounds, see: Eftekhari-Sis et al. (2012a,b). For the biological activity of β-amino see: Arend et al. (1998). For the anti-inflammatory and antimicrobial activity of β-amino see: Jadhav et al. (2008) and Kalluraya et al. (2001), respectively. For information on the Mannich reaction, see: Eftekhari-Sis et al. (2006); Samet et al. (2009); Azizi et al. (2006); Cordova (2004). For related structures, see: Eftekhari-Sis et al. (2012b); Yuan et al. (2007); Fun et al. (2009).
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2–8); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).C19H20N2O3 | F(000) = 688 |
Mr = 324.37 | Dx = 1.297 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 10888 reflections |
a = 9.0535 (8) Å | θ = 1.7–28.1° |
b = 11.9947 (7) Å | µ = 0.09 mm−1 |
c = 17.2267 (15) Å | T = 296 K |
β = 117.355 (6)° | Prism, colorless |
V = 1661.5 (2) Å3 | 0.62 × 0.43 × 0.21 mm |
Z = 4 |
Stoe IPDS 2 diffractometer | 3434 independent reflections |
Radiation source: fine-focus sealed tube | 2210 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
rotation method scans | θmax = 26.5°, θmin = 2.5° |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | h = −11→11 |
Tmin = 0.784, Tmax = 0.958 | k = −15→14 |
10888 measured reflections | l = −21→20 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | w = 1/[σ2(Fo2) + (0.099P)2] where P = (Fo2 + 2Fc2)/3 |
3434 reflections | (Δ/σ)max < 0.001 |
221 parameters | Δρmax = 0.79 e Å−3 |
16 restraints | Δρmin = −0.23 e Å−3 |
C19H20N2O3 | V = 1661.5 (2) Å3 |
Mr = 324.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.0535 (8) Å | µ = 0.09 mm−1 |
b = 11.9947 (7) Å | T = 296 K |
c = 17.2267 (15) Å | 0.62 × 0.43 × 0.21 mm |
β = 117.355 (6)° |
Stoe IPDS 2 diffractometer | 3434 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2210 reflections with I > 2σ(I) |
Tmin = 0.784, Tmax = 0.958 | Rint = 0.043 |
10888 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 16 restraints |
wR(F2) = 0.160 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.79 e Å−3 |
3434 reflections | Δρmin = −0.23 e Å−3 |
221 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 | 0.3530 (2) | 0.26145 (18) | 0.22061 (12) | 0.0453 (5) | |
H1 | 0.2966 | 0.3031 | 0.2482 | 0.054* | |
C2 | 0.2739 (2) | 0.1473 (2) | 0.19939 (13) | 0.0505 (5) | |
C3 | 0.0911 (3) | 0.1470 (3) | 0.13652 (16) | 0.0690 (7) | |
H3A | 0.0301 | 0.1828 | 0.1635 | 0.083* | |
H3B | 0.0522 | 0.0707 | 0.1229 | 0.083* | |
C4 | 0.0580 (3) | 0.2080 (3) | 0.05272 (15) | 0.0731 (8) | |
H4A | 0.1080 | 0.1670 | 0.0223 | 0.088* | |
H4B | −0.0610 | 0.2115 | 0.0149 | 0.088* | |
C5 | 0.1274 (3) | 0.3236 (3) | 0.07141 (16) | 0.0730 (8) | |
H5A | 0.0699 | 0.3667 | 0.0969 | 0.088* | |
H5B | 0.1089 | 0.3592 | 0.0172 | 0.088* | |
C6 | 0.3130 (3) | 0.3223 (2) | 0.13399 (16) | 0.0660 (7) | |
H6A | 0.3532 | 0.3984 | 0.1468 | 0.079* | |
H6B | 0.3713 | 0.2856 | 0.1059 | 0.079* | |
C7 | 0.5407 (2) | 0.26636 (18) | 0.28430 (12) | 0.0429 (5) | |
H7 | 0.5759 | 0.3436 | 0.2840 | 0.052* | |
C8 | 0.5807 (2) | 0.23927 (17) | 0.37935 (12) | 0.0414 (4) | |
C9 | 0.5888 (2) | 0.31751 (17) | 0.44110 (13) | 0.0448 (5) | |
C10 | 0.6289 (3) | 0.2903 (2) | 0.52741 (15) | 0.0574 (6) | |
H10 | 0.6344 | 0.3455 | 0.5666 | 0.069* | |
C11 | 0.6599 (3) | 0.1815 (2) | 0.55354 (16) | 0.0655 (7) | |
H11 | 0.6837 | 0.1613 | 0.6102 | 0.079* | |
C12 | 0.6555 (3) | 0.1022 (2) | 0.49480 (16) | 0.0636 (6) | |
H12 | 0.6772 | 0.0281 | 0.5123 | 0.076* | |
C13 | 0.6193 (3) | 0.13097 (19) | 0.41035 (14) | 0.0531 (5) | |
H13 | 0.6209 | 0.0757 | 0.3729 | 0.064* | |
C14 | 0.8043 (2) | 0.20265 (19) | 0.28812 (12) | 0.0455 (5) | |
C15 | 0.8911 (3) | 0.3024 (2) | 0.31590 (16) | 0.0613 (6) | |
H15 | 0.8341 | 0.3686 | 0.3111 | 0.074* | |
C16 | 1.0631 (3) | 0.3029 (3) | 0.35075 (17) | 0.0752 (8) | |
H16 | 1.1208 | 0.3698 | 0.3693 | 0.090* | |
C17 | 1.1495 (3) | 0.2056 (3) | 0.35827 (16) | 0.0750 (9) | |
H17 | 1.2650 | 0.2063 | 0.3830 | 0.090* | |
C18 | 1.0634 (3) | 0.1077 (3) | 0.32882 (17) | 0.0726 (8) | |
H18 | 1.1208 | 0.0422 | 0.3320 | 0.087* | |
C19 | 0.8934 (3) | 0.1054 (2) | 0.29467 (15) | 0.0580 (6) | |
H19 | 0.8370 | 0.0381 | 0.2757 | 0.070* | |
N1 | 0.6308 (2) | 0.19843 (17) | 0.25075 (11) | 0.0467 (4) | |
N2 | 0.5569 (2) | 0.43539 (16) | 0.41868 (13) | 0.0545 (5) | |
O1 | 0.3490 (2) | 0.06234 (15) | 0.22935 (12) | 0.0718 (5) | |
O2 | 0.4393 (2) | 0.46052 (15) | 0.34977 (12) | 0.0711 (5) | |
O3 | 0.6465 (3) | 0.50448 (17) | 0.47103 (14) | 0.0861 (6) | |
H1A | 0.593 (3) | 0.133 (2) | 0.2363 (14) | 0.046 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0372 (9) | 0.0539 (13) | 0.0416 (10) | 0.0030 (8) | 0.0155 (8) | 0.0015 (9) |
C2 | 0.0409 (10) | 0.0643 (13) | 0.0424 (11) | −0.0054 (8) | 0.0158 (8) | 0.0008 (9) |
C3 | 0.0425 (11) | 0.090 (2) | 0.0587 (14) | −0.0105 (11) | 0.0094 (10) | 0.0033 (13) |
C4 | 0.0445 (12) | 0.115 (3) | 0.0449 (12) | 0.0038 (13) | 0.0080 (10) | −0.0011 (13) |
C5 | 0.0605 (14) | 0.093 (2) | 0.0534 (14) | 0.0169 (13) | 0.0157 (11) | 0.0192 (13) |
C6 | 0.0604 (13) | 0.0680 (17) | 0.0568 (14) | 0.0042 (11) | 0.0160 (11) | 0.0186 (12) |
C7 | 0.0384 (9) | 0.0447 (11) | 0.0438 (10) | −0.0013 (8) | 0.0173 (8) | −0.0015 (9) |
C8 | 0.0294 (8) | 0.0471 (12) | 0.0420 (10) | −0.0005 (7) | 0.0116 (7) | −0.0023 (9) |
C9 | 0.0356 (9) | 0.0486 (12) | 0.0474 (11) | 0.0007 (8) | 0.0166 (8) | −0.0039 (9) |
C10 | 0.0526 (12) | 0.0719 (17) | 0.0474 (12) | 0.0040 (10) | 0.0226 (10) | −0.0071 (11) |
C11 | 0.0619 (13) | 0.086 (2) | 0.0441 (11) | 0.0112 (12) | 0.0205 (10) | 0.0105 (12) |
C12 | 0.0692 (14) | 0.0574 (16) | 0.0569 (14) | 0.0108 (11) | 0.0227 (11) | 0.0139 (12) |
C13 | 0.0545 (11) | 0.0482 (13) | 0.0485 (11) | 0.0039 (9) | 0.0168 (9) | 0.0007 (10) |
C14 | 0.0387 (9) | 0.0631 (14) | 0.0350 (9) | −0.0016 (8) | 0.0171 (8) | 0.0002 (9) |
C15 | 0.0499 (12) | 0.0755 (17) | 0.0601 (13) | −0.0119 (11) | 0.0267 (10) | −0.0143 (12) |
C16 | 0.0541 (14) | 0.111 (2) | 0.0618 (15) | −0.0289 (14) | 0.0275 (12) | −0.0200 (15) |
C17 | 0.0396 (11) | 0.135 (3) | 0.0495 (13) | −0.0052 (14) | 0.0200 (10) | 0.0048 (15) |
C18 | 0.0518 (13) | 0.104 (2) | 0.0636 (15) | 0.0196 (14) | 0.0278 (11) | 0.0205 (15) |
C19 | 0.0481 (11) | 0.0691 (16) | 0.0570 (13) | 0.0066 (10) | 0.0243 (10) | 0.0072 (11) |
N1 | 0.0382 (8) | 0.0505 (12) | 0.0492 (10) | −0.0036 (7) | 0.0184 (7) | −0.0092 (8) |
N2 | 0.0535 (10) | 0.0533 (12) | 0.0605 (12) | −0.0005 (8) | 0.0294 (9) | −0.0071 (9) |
O1 | 0.0614 (10) | 0.0610 (11) | 0.0812 (12) | −0.0048 (7) | 0.0226 (9) | 0.0008 (9) |
O2 | 0.0737 (11) | 0.0559 (11) | 0.0707 (11) | 0.0117 (8) | 0.0220 (9) | 0.0046 (9) |
O3 | 0.0958 (14) | 0.0607 (12) | 0.0903 (13) | −0.0195 (10) | 0.0329 (11) | −0.0274 (10) |
C1—C2 | 1.510 (3) | C9—N2 | 1.459 (3) |
C1—C7 | 1.543 (2) | C10—C11 | 1.367 (4) |
C1—C6 | 1.547 (3) | C10—H10 | 0.9300 |
C1—H1 | 0.9800 | C11—C12 | 1.376 (4) |
C2—O1 | 1.202 (3) | C11—H11 | 0.9300 |
C2—C3 | 1.505 (3) | C12—C13 | 1.380 (3) |
C3—C4 | 1.521 (4) | C12—H12 | 0.9300 |
C3—H3A | 0.9700 | C13—H13 | 0.9300 |
C3—H3B | 0.9700 | C14—C15 | 1.391 (3) |
C4—C5 | 1.494 (4) | C14—C19 | 1.392 (3) |
C4—H4A | 0.9700 | C14—N1 | 1.399 (2) |
C4—H4B | 0.9700 | C15—C16 | 1.388 (3) |
C5—C6 | 1.523 (3) | C15—H15 | 0.9300 |
C5—H5A | 0.9700 | C16—C17 | 1.378 (4) |
C5—H5B | 0.9700 | C16—H16 | 0.9300 |
C6—H6A | 0.9700 | C17—C18 | 1.371 (4) |
C6—H6B | 0.9700 | C17—H17 | 0.9300 |
C7—N1 | 1.448 (3) | C18—C19 | 1.373 (3) |
C7—C8 | 1.541 (3) | C18—H18 | 0.9300 |
C7—H7 | 0.9800 | C19—H19 | 0.9300 |
C8—C13 | 1.387 (3) | N1—H1A | 0.85 (2) |
C8—C9 | 1.395 (3) | N2—O2 | 1.214 (2) |
C9—C10 | 1.398 (3) | N2—O3 | 1.219 (3) |
C2—C1—C7 | 116.84 (17) | C9—C8—C7 | 124.96 (18) |
C2—C1—C6 | 108.61 (18) | C8—C9—C10 | 123.4 (2) |
C7—C1—C6 | 111.16 (16) | C8—C9—N2 | 121.02 (19) |
C2—C1—H1 | 106.5 | C10—C9—N2 | 115.56 (19) |
C7—C1—H1 | 106.5 | C11—C10—C9 | 119.2 (2) |
C6—C1—H1 | 106.5 | C11—C10—H10 | 120.4 |
O1—C2—C3 | 121.7 (2) | C9—C10—H10 | 120.4 |
O1—C2—C1 | 123.57 (18) | C10—C11—C12 | 119.0 (2) |
C3—C2—C1 | 114.8 (2) | C10—C11—H11 | 120.5 |
C2—C3—C4 | 110.71 (19) | C12—C11—H11 | 120.5 |
C2—C3—H3A | 109.5 | C11—C12—C13 | 121.0 (2) |
C4—C3—H3A | 109.5 | C11—C12—H12 | 119.5 |
C2—C3—H3B | 109.5 | C13—C12—H12 | 119.5 |
C4—C3—H3B | 109.5 | C12—C13—C8 | 122.4 (2) |
H3A—C3—H3B | 108.1 | C12—C13—H13 | 118.8 |
C5—C4—C3 | 111.2 (2) | C8—C13—H13 | 118.8 |
C5—C4—H4A | 109.4 | C15—C14—C19 | 118.60 (19) |
C3—C4—H4A | 109.4 | C15—C14—N1 | 121.8 (2) |
C5—C4—H4B | 109.4 | C19—C14—N1 | 119.5 (2) |
C3—C4—H4B | 109.4 | C16—C15—C14 | 119.8 (2) |
H4A—C4—H4B | 108.0 | C16—C15—H15 | 120.1 |
C4—C5—C6 | 111.1 (2) | C14—C15—H15 | 120.1 |
C4—C5—H5A | 109.4 | C17—C16—C15 | 120.9 (3) |
C6—C5—H5A | 109.4 | C17—C16—H16 | 119.6 |
C4—C5—H5B | 109.4 | C15—C16—H16 | 119.6 |
C6—C5—H5B | 109.4 | C18—C17—C16 | 119.3 (2) |
H5A—C5—H5B | 108.0 | C18—C17—H17 | 120.4 |
C5—C6—C1 | 112.4 (2) | C16—C17—H17 | 120.4 |
C5—C6—H6A | 109.1 | C17—C18—C19 | 120.7 (3) |
C1—C6—H6A | 109.1 | C17—C18—H18 | 119.6 |
C5—C6—H6B | 109.1 | C19—C18—H18 | 119.6 |
C1—C6—H6B | 109.1 | C18—C19—C14 | 120.7 (2) |
H6A—C6—H6B | 107.9 | C18—C19—H19 | 119.6 |
N1—C7—C8 | 113.92 (16) | C14—C19—H19 | 119.6 |
N1—C7—C1 | 109.45 (16) | C14—N1—C7 | 121.03 (17) |
C8—C7—C1 | 113.04 (15) | C14—N1—H1A | 112.7 (14) |
N1—C7—H7 | 106.6 | C7—N1—H1A | 114.4 (14) |
C8—C7—H7 | 106.6 | O2—N2—O3 | 122.8 (2) |
C1—C7—H7 | 106.6 | O2—N2—C9 | 118.52 (18) |
C13—C8—C9 | 114.90 (19) | O3—N2—C9 | 118.7 (2) |
C13—C8—C7 | 120.08 (18) | ||
C7—C1—C2—O1 | 0.1 (3) | C8—C9—C10—C11 | −1.0 (3) |
C6—C1—C2—O1 | 126.8 (2) | N2—C9—C10—C11 | 179.8 (2) |
C7—C1—C2—C3 | −179.56 (18) | C9—C10—C11—C12 | 1.9 (3) |
C6—C1—C2—C3 | −52.9 (2) | C10—C11—C12—C13 | −0.4 (4) |
O1—C2—C3—C4 | −125.0 (3) | C11—C12—C13—C8 | −2.1 (4) |
C1—C2—C3—C4 | 54.7 (3) | C9—C8—C13—C12 | 2.9 (3) |
C2—C3—C4—C5 | −55.0 (3) | C7—C8—C13—C12 | −179.79 (19) |
C3—C4—C5—C6 | 56.5 (3) | C19—C14—C15—C16 | −1.2 (3) |
C4—C5—C6—C1 | −56.3 (3) | N1—C14—C15—C16 | −178.5 (2) |
C2—C1—C6—C5 | 52.8 (3) | C14—C15—C16—C17 | 0.0 (4) |
C7—C1—C6—C5 | −177.3 (2) | C15—C16—C17—C18 | 1.6 (4) |
C2—C1—C7—N1 | 56.4 (2) | C16—C17—C18—C19 | −2.0 (4) |
C6—C1—C7—N1 | −69.0 (2) | C17—C18—C19—C14 | 0.8 (4) |
C2—C1—C7—C8 | −71.8 (2) | C15—C14—C19—C18 | 0.8 (3) |
C6—C1—C7—C8 | 162.83 (19) | N1—C14—C19—C18 | 178.2 (2) |
N1—C7—C8—C13 | −32.7 (2) | C15—C14—N1—C7 | −39.6 (3) |
C1—C7—C8—C13 | 93.1 (2) | C19—C14—N1—C7 | 143.1 (2) |
N1—C7—C8—C9 | 144.35 (18) | C8—C7—N1—C14 | −63.0 (2) |
C1—C7—C8—C9 | −89.9 (2) | C1—C7—N1—C14 | 169.39 (18) |
C13—C8—C9—C10 | −1.4 (3) | C8—C9—N2—O2 | 44.2 (3) |
C7—C8—C9—C10 | −178.57 (17) | C10—C9—N2—O2 | −136.5 (2) |
C13—C8—C9—N2 | 177.87 (17) | C8—C9—N2—O3 | −137.9 (2) |
C7—C8—C9—N2 | 0.7 (3) | C10—C9—N2—O3 | 41.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1 | 0.85 (2) | 2.31 (2) | 2.906 (3) | 127.0 (18) |
N1—H1A···O2i | 0.85 (2) | 2.48 (2) | 3.246 (3) | 150.2 (19) |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H20N2O3 |
Mr | 324.37 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 9.0535 (8), 11.9947 (7), 17.2267 (15) |
β (°) | 117.355 (6) |
V (Å3) | 1661.5 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.62 × 0.43 × 0.21 |
Data collection | |
Diffractometer | Stoe IPDS 2 |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.784, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10888, 3434, 2210 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.160, 0.97 |
No. of reflections | 3434 |
No. of parameters | 221 |
No. of restraints | 16 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.79, −0.23 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2–8), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1 | 0.85 (2) | 2.31 (2) | 2.906 (3) | 127.0 (18) |
N1—H1A···O2i | 0.85 (2) | 2.48 (2) | 3.246 (3) | 150.2 (19) |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
Acknowledgements
The research council of the University of Maragheh is acknowledged for financial support.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
β-amino ketones are widely found in natural and un-natural products, which exhibit anti-inflammatory (Jadhav et al., 2008) and antimicrobial (Kalluraya et al., 2001) activities. Mannich reaction (Eftekhari-Sis et al., 2006; Samet et al., 2009; Azizi et al., 2006; Cordova, 2004) is one of the most important basic reactions in organic chemistry for its use in synthesis of β-Amino ketones. We have synthesized the title compound and report its structure here, Fig 1. The cyclohexanone ring adopts chair conformation, and aminomethyl moiety is positioned equatorially on ring at C1.