organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

(Received 17 August 2012; accepted 26 August 2012; online 1 September 2012)

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[Eftekhari-Sis, B., Mohajer, S., Mahdavinia, G. R. & Büyükgüngör, O. (2012a). Tetrahedron Lett. Submitted.],b[Eftekhari-Sis, B., Mohajer, S., Mozaffarnia, S. & Büyükgüngör, O. (2012b). Acta Cryst. E68. Submitted [FB2265].]). For the biological activity of β-amino ketones, see: Arend et al. (1998[Arend, M., Westermann, B. & Risch, N. (1998). Angew. Chem. Int. Ed. 37, 1044-1070.]). For the anti-inflammatory and anti­microbial activity of β-amino ketones, see: Jadhav et al. (2008[Jadhav, V. J., Kulkarni, M. V., Rasal, V. P., Biradar, S. S. & Vinay, M. D. (2008). Eur. J. Med. Chem. 43, 1721-1729.]) and Kalluraya et al. (2001[Kalluraya, B., Isloor, A. M., Chimbalkar, R. & Shenoy, S. (2001). Indian J. Heterocycl. Chem. pp. 239-240.]), respectively. For information on the Mannich reaction, see: Eftekhari-Sis et al. (2006[Eftekhari-Sis, B., Abdollahifar, A., Hashemi, M. M. & Zirak, M. (2006). Eur. J. Org. Chem. pp. 5152-5157.]); Samet et al. (2009[Samet, M., Eftekhari-Sis, B., Hashemi, M. M. & Farmad, F. (2009). Synth. Commun. 39, 4441-4453.]); Azizi et al. (2006[Azizi, N., Torkiyan, L. & Saidi, M. R. (2006). Org. Lett. 8, 2079-2082.]); Cordova (2004[Cordova, A. (2004). Acc. Chem. Res. 37, 102-112.]). For related structures, see: Eftekhari-Sis et al. (2012b[Eftekhari-Sis, B., Mohajer, S., Mozaffarnia, S. & Büyükgüngör, O. (2012b). Acta Cryst. E68. Submitted [FB2265].]); Yuan et al. (2007[Yuan, G.-X., Sun, J.-B., Zhang, L.-H. & Lu, G. (2007). Acta Cryst. E63, o3960.]); Fun et al. (2009[Fun, H.-K., Chantrapromma, S., Rai, S., Shetty, P. & Isloor, A. M. (2009). Acta Cryst. E65, o539-o540.]).

[Scheme 1]

Experimental

Crystal data
  • C19H20N2O3

  • Mr = 324.37

  • Monoclinic, P 21 /c

  • a = 9.0535 (8) Å

  • b = 11.9947 (7) Å

  • c = 17.2267 (15) Å

  • β = 117.355 (6)°

  • V = 1661.5 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.62 × 0.43 × 0.21 mm

Data collection
  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.784, Tmax = 0.958

  • 10888 measured reflections

  • 3434 independent reflections

  • 2210 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.160

  • S = 0.97

  • 3434 reflections

  • 221 parameters

  • 16 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.79 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2–8); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


Comment top

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.

Related literature top

For the synthesis of the title compound and related compounds, see: Eftekhari-Sis et al. (2012a,b). For the biological activity of β-amino ketones, see: Arend et al. (1998). For the anti-inflammatory and antimicrobial activity of β-amino ketones, 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 top

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 crystal structure determination were grown from EtOH.

Refinement top

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.

Structure description top

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.

For the synthesis of the title compound and related compounds, see: Eftekhari-Sis et al. (2012a,b). For the biological activity of β-amino ketones, see: Arend et al. (1998). For the anti-inflammatory and antimicrobial activity of β-amino ketones, 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).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The structure of title compound, showing 35% probability displacement ellipsoids and the atom numbering scheme. Intramolecular hydrogen bond are shown as dashed lines.
[Figure 2] Fig. 2. The stabilization of molecules in the crystal by inter- and intramolecular N—H···O hydrogen bonds and C—H···O interactions.
2-[(Anilino)(2-nitrophenyl)methyl]cyclohexanone top
Crystal data top
C19H20N2O3F(000) = 688
Mr = 324.37Dx = 1.297 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10888 reflections
a = 9.0535 (8) Åθ = 1.7–28.1°
b = 11.9947 (7) ŵ = 0.09 mm1
c = 17.2267 (15) ÅT = 296 K
β = 117.355 (6)°Prism, colorless
V = 1661.5 (2) Å30.62 × 0.43 × 0.21 mm
Z = 4
Data collection top
Stoe IPDS 2
diffractometer
3434 independent reflections
Radiation source: fine-focus sealed tube2210 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
rotation method scansθmax = 26.5°, θmin = 2.5°
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
h = 1111
Tmin = 0.784, Tmax = 0.958k = 1514
10888 measured reflectionsl = 2120
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H 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 parametersΔρmax = 0.79 e Å3
16 restraintsΔρmin = 0.23 e Å3
Crystal data top
C19H20N2O3V = 1661.5 (2) Å3
Mr = 324.37Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.0535 (8) ŵ = 0.09 mm1
b = 11.9947 (7) ÅT = 296 K
c = 17.2267 (15) Å0.62 × 0.43 × 0.21 mm
β = 117.355 (6)°
Data collection top
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 = 0.958Rint = 0.043
10888 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05416 restraints
wR(F2) = 0.160H atoms treated by a mixture of independent and constrained refinement
S = 0.97Δρmax = 0.79 e Å3
3434 reflectionsΔρmin = 0.23 e Å3
221 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3530 (2)0.26145 (18)0.22061 (12)0.0453 (5)
H10.29660.30310.24820.054*
C20.2739 (2)0.1473 (2)0.19939 (13)0.0505 (5)
C30.0911 (3)0.1470 (3)0.13652 (16)0.0690 (7)
H3A0.03010.18280.16350.083*
H3B0.05220.07070.12290.083*
C40.0580 (3)0.2080 (3)0.05272 (15)0.0731 (8)
H4A0.10800.16700.02230.088*
H4B0.06100.21150.01490.088*
C50.1274 (3)0.3236 (3)0.07141 (16)0.0730 (8)
H5A0.06990.36670.09690.088*
H5B0.10890.35920.01720.088*
C60.3130 (3)0.3223 (2)0.13399 (16)0.0660 (7)
H6A0.35320.39840.14680.079*
H6B0.37130.28560.10590.079*
C70.5407 (2)0.26636 (18)0.28430 (12)0.0429 (5)
H70.57590.34360.28400.052*
C80.5807 (2)0.23927 (17)0.37935 (12)0.0414 (4)
C90.5888 (2)0.31751 (17)0.44110 (13)0.0448 (5)
C100.6289 (3)0.2903 (2)0.52741 (15)0.0574 (6)
H100.63440.34550.56660.069*
C110.6599 (3)0.1815 (2)0.55354 (16)0.0655 (7)
H110.68370.16130.61020.079*
C120.6555 (3)0.1022 (2)0.49480 (16)0.0636 (6)
H120.67720.02810.51230.076*
C130.6193 (3)0.13097 (19)0.41035 (14)0.0531 (5)
H130.62090.07570.37290.064*
C140.8043 (2)0.20265 (19)0.28812 (12)0.0455 (5)
C150.8911 (3)0.3024 (2)0.31590 (16)0.0613 (6)
H150.83410.36860.31110.074*
C161.0631 (3)0.3029 (3)0.35075 (17)0.0752 (8)
H161.12080.36980.36930.090*
C171.1495 (3)0.2056 (3)0.35827 (16)0.0750 (9)
H171.26500.20630.38300.090*
C181.0634 (3)0.1077 (3)0.32882 (17)0.0726 (8)
H181.12080.04220.33200.087*
C190.8934 (3)0.1054 (2)0.29467 (15)0.0580 (6)
H190.83700.03810.27570.070*
N10.6308 (2)0.19843 (17)0.25075 (11)0.0467 (4)
N20.5569 (2)0.43539 (16)0.41868 (13)0.0545 (5)
O10.3490 (2)0.06234 (15)0.22935 (12)0.0718 (5)
O20.4393 (2)0.46052 (15)0.34977 (12)0.0711 (5)
O30.6465 (3)0.50448 (17)0.47103 (14)0.0861 (6)
H1A0.593 (3)0.133 (2)0.2363 (14)0.046 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0372 (9)0.0539 (13)0.0416 (10)0.0030 (8)0.0155 (8)0.0015 (9)
C20.0409 (10)0.0643 (13)0.0424 (11)0.0054 (8)0.0158 (8)0.0008 (9)
C30.0425 (11)0.090 (2)0.0587 (14)0.0105 (11)0.0094 (10)0.0033 (13)
C40.0445 (12)0.115 (3)0.0449 (12)0.0038 (13)0.0080 (10)0.0011 (13)
C50.0605 (14)0.093 (2)0.0534 (14)0.0169 (13)0.0157 (11)0.0192 (13)
C60.0604 (13)0.0680 (17)0.0568 (14)0.0042 (11)0.0160 (11)0.0186 (12)
C70.0384 (9)0.0447 (11)0.0438 (10)0.0013 (8)0.0173 (8)0.0015 (9)
C80.0294 (8)0.0471 (12)0.0420 (10)0.0005 (7)0.0116 (7)0.0023 (9)
C90.0356 (9)0.0486 (12)0.0474 (11)0.0007 (8)0.0166 (8)0.0039 (9)
C100.0526 (12)0.0719 (17)0.0474 (12)0.0040 (10)0.0226 (10)0.0071 (11)
C110.0619 (13)0.086 (2)0.0441 (11)0.0112 (12)0.0205 (10)0.0105 (12)
C120.0692 (14)0.0574 (16)0.0569 (14)0.0108 (11)0.0227 (11)0.0139 (12)
C130.0545 (11)0.0482 (13)0.0485 (11)0.0039 (9)0.0168 (9)0.0007 (10)
C140.0387 (9)0.0631 (14)0.0350 (9)0.0016 (8)0.0171 (8)0.0002 (9)
C150.0499 (12)0.0755 (17)0.0601 (13)0.0119 (11)0.0267 (10)0.0143 (12)
C160.0541 (14)0.111 (2)0.0618 (15)0.0289 (14)0.0275 (12)0.0200 (15)
C170.0396 (11)0.135 (3)0.0495 (13)0.0052 (14)0.0200 (10)0.0048 (15)
C180.0518 (13)0.104 (2)0.0636 (15)0.0196 (14)0.0278 (11)0.0205 (15)
C190.0481 (11)0.0691 (16)0.0570 (13)0.0066 (10)0.0243 (10)0.0072 (11)
N10.0382 (8)0.0505 (12)0.0492 (10)0.0036 (7)0.0184 (7)0.0092 (8)
N20.0535 (10)0.0533 (12)0.0605 (12)0.0005 (8)0.0294 (9)0.0071 (9)
O10.0614 (10)0.0610 (11)0.0812 (12)0.0048 (7)0.0226 (9)0.0008 (9)
O20.0737 (11)0.0559 (11)0.0707 (11)0.0117 (8)0.0220 (9)0.0046 (9)
O30.0958 (14)0.0607 (12)0.0903 (13)0.0195 (10)0.0329 (11)0.0274 (10)
Geometric parameters (Å, º) top
C1—C21.510 (3)C9—N21.459 (3)
C1—C71.543 (2)C10—C111.367 (4)
C1—C61.547 (3)C10—H100.9300
C1—H10.9800C11—C121.376 (4)
C2—O11.202 (3)C11—H110.9300
C2—C31.505 (3)C12—C131.380 (3)
C3—C41.521 (4)C12—H120.9300
C3—H3A0.9700C13—H130.9300
C3—H3B0.9700C14—C151.391 (3)
C4—C51.494 (4)C14—C191.392 (3)
C4—H4A0.9700C14—N11.399 (2)
C4—H4B0.9700C15—C161.388 (3)
C5—C61.523 (3)C15—H150.9300
C5—H5A0.9700C16—C171.378 (4)
C5—H5B0.9700C16—H160.9300
C6—H6A0.9700C17—C181.371 (4)
C6—H6B0.9700C17—H170.9300
C7—N11.448 (3)C18—C191.373 (3)
C7—C81.541 (3)C18—H180.9300
C7—H70.9800C19—H190.9300
C8—C131.387 (3)N1—H1A0.85 (2)
C8—C91.395 (3)N2—O21.214 (2)
C9—C101.398 (3)N2—O31.219 (3)
C2—C1—C7116.84 (17)C9—C8—C7124.96 (18)
C2—C1—C6108.61 (18)C8—C9—C10123.4 (2)
C7—C1—C6111.16 (16)C8—C9—N2121.02 (19)
C2—C1—H1106.5C10—C9—N2115.56 (19)
C7—C1—H1106.5C11—C10—C9119.2 (2)
C6—C1—H1106.5C11—C10—H10120.4
O1—C2—C3121.7 (2)C9—C10—H10120.4
O1—C2—C1123.57 (18)C10—C11—C12119.0 (2)
C3—C2—C1114.8 (2)C10—C11—H11120.5
C2—C3—C4110.71 (19)C12—C11—H11120.5
C2—C3—H3A109.5C11—C12—C13121.0 (2)
C4—C3—H3A109.5C11—C12—H12119.5
C2—C3—H3B109.5C13—C12—H12119.5
C4—C3—H3B109.5C12—C13—C8122.4 (2)
H3A—C3—H3B108.1C12—C13—H13118.8
C5—C4—C3111.2 (2)C8—C13—H13118.8
C5—C4—H4A109.4C15—C14—C19118.60 (19)
C3—C4—H4A109.4C15—C14—N1121.8 (2)
C5—C4—H4B109.4C19—C14—N1119.5 (2)
C3—C4—H4B109.4C16—C15—C14119.8 (2)
H4A—C4—H4B108.0C16—C15—H15120.1
C4—C5—C6111.1 (2)C14—C15—H15120.1
C4—C5—H5A109.4C17—C16—C15120.9 (3)
C6—C5—H5A109.4C17—C16—H16119.6
C4—C5—H5B109.4C15—C16—H16119.6
C6—C5—H5B109.4C18—C17—C16119.3 (2)
H5A—C5—H5B108.0C18—C17—H17120.4
C5—C6—C1112.4 (2)C16—C17—H17120.4
C5—C6—H6A109.1C17—C18—C19120.7 (3)
C1—C6—H6A109.1C17—C18—H18119.6
C5—C6—H6B109.1C19—C18—H18119.6
C1—C6—H6B109.1C18—C19—C14120.7 (2)
H6A—C6—H6B107.9C18—C19—H19119.6
N1—C7—C8113.92 (16)C14—C19—H19119.6
N1—C7—C1109.45 (16)C14—N1—C7121.03 (17)
C8—C7—C1113.04 (15)C14—N1—H1A112.7 (14)
N1—C7—H7106.6C7—N1—H1A114.4 (14)
C8—C7—H7106.6O2—N2—O3122.8 (2)
C1—C7—H7106.6O2—N2—C9118.52 (18)
C13—C8—C9114.90 (19)O3—N2—C9118.7 (2)
C13—C8—C7120.08 (18)
C7—C1—C2—O10.1 (3)C8—C9—C10—C111.0 (3)
C6—C1—C2—O1126.8 (2)N2—C9—C10—C11179.8 (2)
C7—C1—C2—C3179.56 (18)C9—C10—C11—C121.9 (3)
C6—C1—C2—C352.9 (2)C10—C11—C12—C130.4 (4)
O1—C2—C3—C4125.0 (3)C11—C12—C13—C82.1 (4)
C1—C2—C3—C454.7 (3)C9—C8—C13—C122.9 (3)
C2—C3—C4—C555.0 (3)C7—C8—C13—C12179.79 (19)
C3—C4—C5—C656.5 (3)C19—C14—C15—C161.2 (3)
C4—C5—C6—C156.3 (3)N1—C14—C15—C16178.5 (2)
C2—C1—C6—C552.8 (3)C14—C15—C16—C170.0 (4)
C7—C1—C6—C5177.3 (2)C15—C16—C17—C181.6 (4)
C2—C1—C7—N156.4 (2)C16—C17—C18—C192.0 (4)
C6—C1—C7—N169.0 (2)C17—C18—C19—C140.8 (4)
C2—C1—C7—C871.8 (2)C15—C14—C19—C180.8 (3)
C6—C1—C7—C8162.83 (19)N1—C14—C19—C18178.2 (2)
N1—C7—C8—C1332.7 (2)C15—C14—N1—C739.6 (3)
C1—C7—C8—C1393.1 (2)C19—C14—N1—C7143.1 (2)
N1—C7—C8—C9144.35 (18)C8—C7—N1—C1463.0 (2)
C1—C7—C8—C989.9 (2)C1—C7—N1—C14169.39 (18)
C13—C8—C9—C101.4 (3)C8—C9—N2—O244.2 (3)
C7—C8—C9—C10178.57 (17)C10—C9—N2—O2136.5 (2)
C13—C8—C9—N2177.87 (17)C8—C9—N2—O3137.9 (2)
C7—C8—C9—N20.7 (3)C10—C9—N2—O341.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.85 (2)2.31 (2)2.906 (3)127.0 (18)
N1—H1A···O2i0.85 (2)2.48 (2)3.246 (3)150.2 (19)
Symmetry code: (i) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC19H20N2O3
Mr324.37
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)9.0535 (8), 11.9947 (7), 17.2267 (15)
β (°) 117.355 (6)
V3)1661.5 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.62 × 0.43 × 0.21
Data collection
DiffractometerStoe IPDS 2
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.784, 0.958
No. of measured, independent and
observed [I > 2σ(I)] reflections
10888, 3434, 2210
Rint0.043
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.160, 0.97
No. of reflections3434
No. of parameters221
No. of restraints16
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.85 (2)2.31 (2)2.906 (3)127.0 (18)
N1—H1A···O2i0.85 (2)2.48 (2)3.246 (3)150.2 (19)
Symmetry code: (i) x+1, y1/2, z+1/2.
 

Acknowledgements

The research council of the University of Maragheh is acknowledged for financial support.

References

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