organic compounds
2-[Anilino(phenyl)methyl]cycloheptanone
aDepartment of Chemistry, University of Maragheh, Maragheh, Iran, bDepartment of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran, and cDepartment of Physics, Ondokuz Mayıs University, TR-55139, Samsun, Turkey
*Correspondence e-mail: eftekharisis@maragheh.ac.ir
In the title compound, C20H23NO, the cycloheptanone ring adopts a twist-chair conformation, with the aminomethyl substituent in an equatorial position. The of the two stereocenters is R,R. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into chains along [100].
Related literature
For the synthesis of title compound and related compounds, see: Eftekhari-Sis et al. (2013). For the biological activity of β-amino see: Arend et al. (1998); Jadhav et al. (2008); Kalluraya et al. (2001). For information on the Mannich reaction, see, for example: Eftekhari-Sis et al. (2006); Azizi et al. (2006); Cordova (2004). For the crystal structures of related compounds, see: Eftekhari-Sis et al. (2012); Yuan et al. (2007); Fun et al. (2009). For puckering parameters, see: Evans & Boeyens (1989).
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, 2008); 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/S1600536812050659/fy2069sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812050659/fy2069Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812050659/fy2069Isup3.mol
Supporting information file. DOI: https://doi.org/10.1107/S1600536812050659/fy2069Isup4.cml
The title compound was obtained by adding of 0.04 g of Laponite-HPMC nano composite (Eftekhari-Sis et al., 2013) to a mixture of 0.5 mmol of benzaldehyde, 0.5 mmol of aniline and 3 equiv. of cycloheptanone and stirring at room temperature for 24 h. After completion of the reaction, 5 ml EtOH was added and the catalyst was removed by filtration. The filtrate was concentrated under reduced pressure. The obtained crude product was recrystallized from EtOH to afford the title compound in 60% yield. Colorless crystals suitable for
determination were grown from 96% 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 and allowed to refine freely.
Mannich reaction (Eftekhari-Sis et al., 2006; Azizi et al., 2006; Cordova, 2004) is one of the most important basic reactions in organic chemistry for its use in natural product and pharmaceutical syntheses due to formation of C—C and C—N bonds, simultaneously, to furnish β-amino which exhibit biological activity such as anti-inflammatory (Jadhav et al., 2008) and antimicrobial (Kalluraya et al., 2001) activities. We have synthesized the title compound and report its structure here, Fig 1. The cycloheptanone ring adopts twist-chair conformation, with puckering parameters of Q(2) = 0.539 (2) Å, Φ(2) = 41.7 (2)° and Q(3) = 0.644 (2) Å, Φ(3) = 319.2 (2)° (Evans & Boeyens, 1989). The aminomethyl moiety is positioned equatorially on the ring at C1.
For the synthesis of title compound and related compounds, see: Eftekhari-Sis et al. (2013). For the biological activity of β-amino see: Arend et al. (1998); Jadhav et al. (2008); Kalluraya et al. (2001). For information on the Mannich reaction, see, for example: Eftekhari-Sis et al. (2006); Azizi et al. (2006); Cordova (2004). For the crystal structures of related compounds, see: Eftekhari-Sis et al. (2012); Yuan et al. (2007); Fun et al. (2009). For puckering parameters, see: Evans & Boeyens (1989).
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, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).C20H23NO | F(000) = 632 |
Mr = 293.39 | Dx = 1.169 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 10757 reflections |
a = 5.7534 (4) Å | θ = 1.7–28.0° |
b = 16.1336 (8) Å | µ = 0.07 mm−1 |
c = 18.1980 (13) Å | T = 296 K |
β = 99.371 (6)° | Prism, colourless |
V = 1666.65 (19) Å3 | 0.72 × 0.56 × 0.27 mm |
Z = 4 |
Stoe IPDS 2 diffractometer | 3449 independent reflections |
Radiation source: fine-focus sealed tube | 2170 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
rotation method scans | θmax = 26.5°, θmin = 1.7° |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | h = −7→7 |
Tmin = 0.965, Tmax = 0.985 | k = −20→20 |
10757 measured reflections | l = −22→18 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0722P)2] where P = (Fo2 + 2Fc2)/3 |
3449 reflections | (Δ/σ)max < 0.001 |
203 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
C20H23NO | V = 1666.65 (19) Å3 |
Mr = 293.39 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.7534 (4) Å | µ = 0.07 mm−1 |
b = 16.1336 (8) Å | T = 296 K |
c = 18.1980 (13) Å | 0.72 × 0.56 × 0.27 mm |
β = 99.371 (6)° |
Stoe IPDS 2 diffractometer | 3449 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2170 reflections with I > 2σ(I) |
Tmin = 0.965, Tmax = 0.985 | Rint = 0.041 |
10757 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.26 e Å−3 |
3449 reflections | Δρmin = −0.13 e Å−3 |
203 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 | 0.4026 (3) | 0.45073 (9) | 0.32943 (9) | 0.0508 (4) | |
H1 | 0.5213 | 0.4211 | 0.3065 | 0.061* | |
C2 | 0.1676 (3) | 0.41004 (10) | 0.30531 (10) | 0.0545 (4) | |
C3 | 0.1590 (3) | 0.31909 (11) | 0.28983 (11) | 0.0680 (5) | |
H3A | 0.1590 | 0.3111 | 0.2370 | 0.082* | |
H3B | 0.0108 | 0.2978 | 0.3008 | 0.082* | |
C4 | 0.3563 (4) | 0.26786 (11) | 0.33231 (12) | 0.0750 (6) | |
H4A | 0.3205 | 0.2097 | 0.3229 | 0.090* | |
H4B | 0.5002 | 0.2801 | 0.3131 | 0.090* | |
C5 | 0.3998 (5) | 0.28183 (13) | 0.41489 (13) | 0.0919 (7) | |
H5A | 0.2488 | 0.2880 | 0.4315 | 0.110* | |
H5B | 0.4747 | 0.2328 | 0.4388 | 0.110* | |
C6 | 0.5488 (5) | 0.35543 (15) | 0.44101 (12) | 0.0922 (7) | |
H6A | 0.5733 | 0.3557 | 0.4950 | 0.111* | |
H6B | 0.7017 | 0.3476 | 0.4261 | 0.111* | |
C7 | 0.4594 (4) | 0.43901 (13) | 0.41458 (11) | 0.0786 (6) | |
H7A | 0.5761 | 0.4800 | 0.4346 | 0.094* | |
H7B | 0.3177 | 0.4505 | 0.4353 | 0.094* | |
C8 | 0.4030 (3) | 0.54291 (9) | 0.30610 (10) | 0.0533 (4) | |
H8 | 0.2812 | 0.5716 | 0.3283 | 0.064* | |
C9 | 0.5035 (3) | 0.52774 (10) | 0.17700 (11) | 0.0606 (5) | |
H9 | 0.6439 | 0.5026 | 0.1982 | 0.073* | |
C10 | 0.4556 (4) | 0.53841 (12) | 0.10111 (12) | 0.0726 (5) | |
H10 | 0.5642 | 0.5210 | 0.0717 | 0.087* | |
C11 | 0.2490 (4) | 0.57456 (13) | 0.06854 (13) | 0.0801 (6) | |
H11 | 0.2159 | 0.5810 | 0.0171 | 0.096* | |
C12 | 0.0910 (4) | 0.60127 (14) | 0.11243 (14) | 0.0850 (7) | |
H12 | −0.0489 | 0.6264 | 0.0907 | 0.102* | |
C13 | 0.1397 (3) | 0.59089 (12) | 0.18865 (12) | 0.0713 (5) | |
H13 | 0.0314 | 0.6093 | 0.2178 | 0.086* | |
C14 | 0.3459 (3) | 0.55379 (9) | 0.22262 (10) | 0.0530 (4) | |
C15 | 0.6636 (3) | 0.65940 (9) | 0.36011 (9) | 0.0525 (4) | |
C16 | 0.8846 (3) | 0.68313 (11) | 0.39812 (10) | 0.0604 (4) | |
H16 | 1.0051 | 0.6441 | 0.4065 | 0.073* | |
C17 | 0.9275 (4) | 0.76247 (12) | 0.42320 (12) | 0.0706 (5) | |
H17 | 1.0764 | 0.7766 | 0.4481 | 0.085* | |
C18 | 0.7531 (4) | 0.82152 (12) | 0.41206 (12) | 0.0760 (6) | |
H18 | 0.7823 | 0.8754 | 0.4293 | 0.091* | |
C19 | 0.5343 (4) | 0.79933 (11) | 0.37481 (12) | 0.0688 (5) | |
H19 | 0.4152 | 0.8389 | 0.3671 | 0.083* | |
C20 | 0.4877 (3) | 0.71963 (10) | 0.34864 (10) | 0.0587 (4) | |
H20 | 0.3387 | 0.7062 | 0.3233 | 0.070* | |
N1 | 0.6284 (3) | 0.57845 (9) | 0.33722 (10) | 0.0661 (5) | |
O1 | −0.0127 (2) | 0.44979 (8) | 0.30255 (10) | 0.0854 (5) | |
H1A | 0.751 (3) | 0.5457 (11) | 0.3392 (10) | 0.064 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0554 (9) | 0.0428 (8) | 0.0545 (10) | 0.0063 (7) | 0.0095 (7) | −0.0041 (7) |
C2 | 0.0518 (9) | 0.0529 (9) | 0.0604 (11) | 0.0067 (8) | 0.0142 (8) | 0.0069 (8) |
C3 | 0.0697 (11) | 0.0561 (10) | 0.0797 (13) | −0.0070 (9) | 0.0166 (9) | −0.0084 (9) |
C4 | 0.0957 (15) | 0.0449 (9) | 0.0878 (15) | 0.0060 (10) | 0.0253 (11) | 0.0033 (9) |
C5 | 0.132 (2) | 0.0664 (13) | 0.0802 (16) | 0.0179 (13) | 0.0271 (14) | 0.0195 (11) |
C6 | 0.1148 (18) | 0.0980 (17) | 0.0584 (13) | 0.0108 (15) | −0.0023 (12) | 0.0184 (11) |
C7 | 0.1024 (16) | 0.0695 (12) | 0.0605 (12) | 0.0015 (11) | 0.0029 (11) | −0.0085 (10) |
C8 | 0.0482 (9) | 0.0410 (8) | 0.0709 (11) | 0.0037 (7) | 0.0104 (8) | −0.0043 (7) |
C9 | 0.0577 (10) | 0.0510 (9) | 0.0719 (13) | 0.0038 (8) | 0.0067 (9) | −0.0009 (8) |
C10 | 0.0826 (14) | 0.0633 (12) | 0.0738 (14) | 0.0020 (10) | 0.0182 (11) | −0.0008 (9) |
C11 | 0.0962 (16) | 0.0693 (12) | 0.0719 (13) | 0.0007 (12) | 0.0054 (12) | 0.0129 (10) |
C12 | 0.0760 (14) | 0.0830 (14) | 0.0903 (17) | 0.0155 (11) | −0.0031 (12) | 0.0220 (12) |
C13 | 0.0606 (11) | 0.0674 (11) | 0.0857 (15) | 0.0125 (9) | 0.0110 (10) | 0.0134 (10) |
C14 | 0.0509 (9) | 0.0348 (7) | 0.0730 (12) | −0.0021 (7) | 0.0092 (8) | 0.0022 (7) |
C15 | 0.0585 (10) | 0.0456 (8) | 0.0551 (10) | −0.0011 (7) | 0.0142 (7) | −0.0021 (7) |
C16 | 0.0588 (10) | 0.0578 (10) | 0.0639 (11) | 0.0009 (8) | 0.0076 (8) | −0.0071 (8) |
C17 | 0.0700 (12) | 0.0648 (11) | 0.0757 (13) | −0.0106 (10) | 0.0076 (10) | −0.0152 (9) |
C18 | 0.0901 (14) | 0.0522 (10) | 0.0873 (15) | −0.0114 (10) | 0.0198 (11) | −0.0138 (10) |
C19 | 0.0754 (12) | 0.0462 (9) | 0.0876 (14) | 0.0064 (9) | 0.0215 (10) | 0.0000 (9) |
C20 | 0.0591 (10) | 0.0469 (9) | 0.0707 (12) | 0.0001 (8) | 0.0122 (8) | 0.0007 (8) |
N1 | 0.0520 (9) | 0.0463 (8) | 0.0961 (13) | 0.0057 (7) | 0.0010 (8) | −0.0161 (7) |
O1 | 0.0558 (8) | 0.0696 (9) | 0.1328 (14) | 0.0105 (7) | 0.0216 (8) | 0.0106 (8) |
C1—C2 | 1.502 (2) | C9—C14 | 1.390 (2) |
C1—C7 | 1.542 (2) | C9—H9 | 0.9300 |
C1—C8 | 1.547 (2) | C10—C11 | 1.369 (3) |
C1—H1 | 0.9800 | C10—H10 | 0.9300 |
C2—O1 | 1.214 (2) | C11—C12 | 1.373 (3) |
C2—C3 | 1.493 (2) | C11—H11 | 0.9300 |
C3—C4 | 1.511 (3) | C12—C13 | 1.380 (3) |
C3—H3A | 0.9700 | C12—H12 | 0.9300 |
C3—H3B | 0.9700 | C13—C14 | 1.382 (2) |
C4—C5 | 1.500 (3) | C13—H13 | 0.9300 |
C4—H4A | 0.9700 | C15—N1 | 1.376 (2) |
C4—H4B | 0.9700 | C15—C20 | 1.394 (2) |
C5—C6 | 1.496 (3) | C15—C16 | 1.399 (2) |
C5—H5A | 0.9700 | C16—C17 | 1.368 (2) |
C5—H5B | 0.9700 | C16—H16 | 0.9300 |
C6—C7 | 1.495 (3) | C17—C18 | 1.375 (3) |
C6—H6A | 0.9700 | C17—H17 | 0.9300 |
C6—H6B | 0.9700 | C18—C19 | 1.376 (3) |
C7—H7A | 0.9700 | C18—H18 | 0.9300 |
C7—H7B | 0.9700 | C19—C20 | 1.382 (2) |
C8—N1 | 1.446 (2) | C19—H19 | 0.9300 |
C8—C14 | 1.511 (2) | C20—H20 | 0.9300 |
C8—H8 | 0.9800 | N1—H1A | 0.879 (19) |
C9—C10 | 1.374 (3) | ||
C2—C1—C7 | 105.86 (14) | N1—C8—H8 | 107.9 |
C2—C1—C8 | 112.43 (13) | C14—C8—H8 | 107.9 |
C7—C1—C8 | 112.58 (14) | C1—C8—H8 | 107.9 |
C2—C1—H1 | 108.6 | C10—C9—C14 | 121.25 (17) |
C7—C1—H1 | 108.6 | C10—C9—H9 | 119.4 |
C8—C1—H1 | 108.6 | C14—C9—H9 | 119.4 |
O1—C2—C3 | 120.63 (16) | C11—C10—C9 | 120.4 (2) |
O1—C2—C1 | 120.23 (15) | C11—C10—H10 | 119.8 |
C3—C2—C1 | 119.02 (14) | C9—C10—H10 | 119.8 |
C2—C3—C4 | 116.21 (16) | C10—C11—C12 | 119.5 (2) |
C2—C3—H3A | 108.2 | C10—C11—H11 | 120.3 |
C4—C3—H3A | 108.2 | C12—C11—H11 | 120.3 |
C2—C3—H3B | 108.2 | C11—C12—C13 | 120.1 (2) |
C4—C3—H3B | 108.2 | C11—C12—H12 | 120.0 |
H3A—C3—H3B | 107.4 | C13—C12—H12 | 120.0 |
C5—C4—C3 | 114.78 (17) | C12—C13—C14 | 121.4 (2) |
C5—C4—H4A | 108.6 | C12—C13—H13 | 119.3 |
C3—C4—H4A | 108.6 | C14—C13—H13 | 119.3 |
C5—C4—H4B | 108.6 | C13—C14—C9 | 117.37 (18) |
C3—C4—H4B | 108.6 | C13—C14—C8 | 122.03 (16) |
H4A—C4—H4B | 107.5 | C9—C14—C8 | 120.59 (15) |
C6—C5—C4 | 115.53 (18) | N1—C15—C20 | 123.29 (16) |
C6—C5—H5A | 108.4 | N1—C15—C16 | 119.13 (15) |
C4—C5—H5A | 108.4 | C20—C15—C16 | 117.57 (15) |
C6—C5—H5B | 108.4 | C17—C16—C15 | 121.42 (17) |
C4—C5—H5B | 108.4 | C17—C16—H16 | 119.3 |
H5A—C5—H5B | 107.5 | C15—C16—H16 | 119.3 |
C7—C6—C5 | 117.68 (19) | C16—C17—C18 | 120.77 (18) |
C7—C6—H6A | 107.9 | C16—C17—H17 | 119.6 |
C5—C6—H6A | 107.9 | C18—C17—H17 | 119.6 |
C7—C6—H6B | 107.9 | C17—C18—C19 | 118.66 (17) |
C5—C6—H6B | 107.9 | C17—C18—H18 | 120.7 |
H6A—C6—H6B | 107.2 | C19—C18—H18 | 120.7 |
C6—C7—C1 | 116.06 (17) | C18—C19—C20 | 121.50 (18) |
C6—C7—H7A | 108.3 | C18—C19—H19 | 119.3 |
C1—C7—H7A | 108.3 | C20—C19—H19 | 119.3 |
C6—C7—H7B | 108.3 | C19—C20—C15 | 120.08 (17) |
C1—C7—H7B | 108.3 | C19—C20—H20 | 120.0 |
H7A—C7—H7B | 107.4 | C15—C20—H20 | 120.0 |
N1—C8—C14 | 112.45 (14) | C15—N1—C8 | 124.99 (15) |
N1—C8—C1 | 108.37 (13) | C15—N1—H1A | 118.8 (12) |
C14—C8—C1 | 112.20 (13) | C8—N1—H1A | 116.2 (11) |
C7—C1—C2—O1 | 90.59 (19) | C12—C13—C14—C9 | 0.4 (3) |
C8—C1—C2—O1 | −32.7 (2) | C12—C13—C14—C8 | 179.25 (17) |
C7—C1—C2—C3 | −85.34 (18) | C10—C9—C14—C13 | −0.1 (2) |
C8—C1—C2—C3 | 151.35 (16) | C10—C9—C14—C8 | −178.96 (15) |
O1—C2—C3—C4 | −147.48 (19) | N1—C8—C14—C13 | −125.11 (17) |
C1—C2—C3—C4 | 28.4 (2) | C1—C8—C14—C13 | 112.42 (17) |
C2—C3—C4—C5 | 50.6 (2) | N1—C8—C14—C9 | 53.71 (18) |
C3—C4—C5—C6 | −82.4 (3) | C1—C8—C14—C9 | −68.77 (18) |
C4—C5—C6—C7 | 61.6 (3) | N1—C15—C16—C17 | −178.84 (17) |
C5—C6—C7—C1 | −56.2 (3) | C20—C15—C16—C17 | 0.0 (3) |
C2—C1—C7—C6 | 78.4 (2) | C15—C16—C17—C18 | 0.3 (3) |
C8—C1—C7—C6 | −158.42 (19) | C16—C17—C18—C19 | −0.3 (3) |
C2—C1—C8—N1 | 175.01 (14) | C17—C18—C19—C20 | −0.1 (3) |
C7—C1—C8—N1 | 55.55 (19) | C18—C19—C20—C15 | 0.4 (3) |
C2—C1—C8—C14 | −60.23 (18) | N1—C15—C20—C19 | 178.42 (18) |
C7—C1—C8—C14 | −179.69 (15) | C16—C15—C20—C19 | −0.4 (3) |
C14—C9—C10—C11 | −0.6 (3) | C20—C15—N1—C8 | −7.0 (3) |
C9—C10—C11—C12 | 1.0 (3) | C16—C15—N1—C8 | 171.72 (16) |
C10—C11—C12—C13 | −0.7 (3) | C14—C8—N1—C15 | 87.9 (2) |
C11—C12—C13—C14 | 0.0 (3) | C1—C8—N1—C15 | −147.48 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.879 (19) | 2.23 (2) | 3.065 (2) | 158.4 (16) |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C20H23NO |
Mr | 293.39 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 5.7534 (4), 16.1336 (8), 18.1980 (13) |
β (°) | 99.371 (6) |
V (Å3) | 1666.65 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.72 × 0.56 × 0.27 |
Data collection | |
Diffractometer | Stoe IPDS 2 |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.965, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10757, 3449, 2170 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.136, 1.01 |
No. of reflections | 3449 |
No. of parameters | 203 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.26, −0.13 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.879 (19) | 2.23 (2) | 3.065 (2) | 158.4 (16) |
Symmetry code: (i) x+1, y, z. |
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.
Mannich reaction (Eftekhari-Sis et al., 2006; Azizi et al., 2006; Cordova, 2004) is one of the most important basic reactions in organic chemistry for its use in natural product and pharmaceutical syntheses due to formation of C—C and C—N bonds, simultaneously, to furnish β-amino ketones, which exhibit biological activity such as anti-inflammatory (Jadhav et al., 2008) and antimicrobial (Kalluraya et al., 2001) activities. We have synthesized the title compound and report its structure here, Fig 1. The cycloheptanone ring adopts twist-chair conformation, with puckering parameters of Q(2) = 0.539 (2) Å, Φ(2) = 41.7 (2)° and Q(3) = 0.644 (2) Å, Φ(3) = 319.2 (2)° (Evans & Boeyens, 1989). The aminomethyl moiety is positioned equatorially on the ring at C1.