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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(E)-2-[(1-Benzyl­piperidin-4-yl)imino­meth­yl]phenol

aState Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, People's Republic of China, and bSchool of Life Science and Technology, University of Electronic Science and Technology of China, Chengdu 610054, People's Republic of China
*Correspondence e-mail: fangrq@uestc.edu.cn

(Received 23 November 2011; accepted 2 December 2011; online 10 December 2011)

There are two mol­ecules in the asymmetric unit of the title compound, C19H22N2O. Both mol­ecules have an E conformation about their C=N bonds and both piperdine rings adopt chair conformations with their N atoms adopting pyramidal geometries [bond angle sums = 329.8 (4) and 330.2 (4)°]. Both mol­ecules feature an intra­molecular O—H⋯N hydrogen bond, which generates an S(6) ring. The dihedral angles between the phenyl and benzene ring planes are 45.97 (18) and 66.0 (2)°. Short O—H⋯O contacts occur in the crystal.

Related literature

For a related structure, see: Stilinovic et al. (2008[Stilinovic, V., Cincic, D. & Kaitner, B. (2008). Acta. Chim. Solv. 55, 874-879.]).

[Scheme 1]

Experimental

Crystal data
  • C19H22N2O

  • Mr = 294.39

  • Monoclinic, P 21 /c

  • a = 10.603 (2) Å

  • b = 9.6330 (19) Å

  • c = 32.595 (7) Å

  • β = 95.60 (3)°

  • V = 3313.3 (11) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 293 K

  • 0.40 × 0.40 × 0.20 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.971, Tmax = 0.986

  • 6837 measured reflections

  • 6473 independent reflections

  • 2764 reflections with I > 2σ(I)

  • Rint = 0.117

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.082

  • wR(F2) = 0.268

  • S = 1.09

  • 6473 reflections

  • 406 parameters

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

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N1 1.01 (8) 1.73 (7) 2.597 (5) 141 (6)
O2—H2A⋯N3 1.05 (7) 1.66 (7) 2.588 (6) 144 (5)
O1—H1⋯O1i 1.01 (8) 2.49 (7) 2.869 (7) 102 (5)
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, 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, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The cystal structure of 1,4-bis-((1-benzylpiperidin-4-ylimino)methyl)benzene has been reported, which was synthesized by 4-amino-N-benzylpiperidine and terephtaldialdehyde. (Stilinovic et al., 2008). While, the title compund has been obtained by 4-amino-N-benzylpiperidine and salicyaldehyde. The molecular structure of title compound (I) with atom numbering are given in is shown in Fig. 1, there are two (E)-2-((1-benzylpiperidin-4-ylimino)methyl)phenol in an asymmetric unit. Both C7=N1 and C26=N3 are of the E configuration, with the bond lengths of 1.262 (6) and 1.267 (6) Å. The torsion angle of C9—C8—N1—C7 and C28—C27—N3—C26 is -118.2 (5) ° and 107.9 (5) °, respectively. The Rms of two six-member piperidine rings of chair conformation are 0.2354 Å and 0.2322 Å. The dihedral angles between two phenyl planes in two molecules are 45.97 (18) and 65.97 (21)°. In each molecule, intramolecular O—H···N hydrogen bonds occur, and molecules are linked through intermolecular O—H···O hydrogen bonds to form a packing network along b axis.(Fig. 2).

Related literature top

For a related structure, see: Stilinovic et al. (2008).

Experimental top

The title compound was prepared by stirring a mixture of salicylaldehyde (122 mg, 1 mmol) and 4-amino-N-benzylpiperidine (190 mg, 1 mmol) in methanol (15 ml) for 4 h at room temperature. After keeping the solution in air for 3 d, yellow block-shaped crystals of (I) were formed. The crystals were isolated, washed three times with methanol and dried in a vacuum desiccator containing anhydrous CaCl2.

Refinement top

All the H atoms, were placed in idealized positions (C—H = 0.93- 0.96 Å, O—H = 0.82 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The structure of (I) showing 35% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of (I), viewed along the b axis. Hydrogen bonds are shown as dashed lines.
(E)-2-[(1-Benzylpiperidin-4-yl)iminomethyl]phenol top
Crystal data top
C19H22N2OF(000) = 1264
Mr = 294.39Dx = 1.180 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2318 reflections
a = 10.603 (2) Åθ = 2.6–24.7°
b = 9.6330 (19) ŵ = 0.07 mm1
c = 32.595 (7) ÅT = 293 K
β = 95.60 (3)°Block, yellow
V = 3313.3 (11) Å30.40 × 0.40 × 0.20 mm
Z = 8
Data collection top
Enraf–Nonius CAD-4
diffractometer
2764 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.117
Graphite monochromatorθmax = 26.0°, θmin = 1.3°
ω/2θ scanh = 013
Absorption correction: ψ scan
(North et al., 1968)
k = 011
Tmin = 0.971, Tmax = 0.986l = 4039
6837 measured reflections3 standard reflections every 200 reflections
6473 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.082H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.268 w = 1/[σ2(Fo2) + (0.0628P)2 + 4.8871P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
6473 reflectionsΔρmax = 0.22 e Å3
406 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0089 (11)
Crystal data top
C19H22N2OV = 3313.3 (11) Å3
Mr = 294.39Z = 8
Monoclinic, P21/cMo Kα radiation
a = 10.603 (2) ŵ = 0.07 mm1
b = 9.6330 (19) ÅT = 293 K
c = 32.595 (7) Å0.40 × 0.40 × 0.20 mm
β = 95.60 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
2764 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.117
Tmin = 0.971, Tmax = 0.9863 standard reflections every 200 reflections
6837 measured reflections intensity decay: 1%
6473 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0820 restraints
wR(F2) = 0.268H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.22 e Å3
6473 reflectionsΔρmin = 0.20 e Å3
406 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
C10.3352 (5)0.6495 (5)1.08004 (15)0.0556 (13)
C20.3051 (6)0.6876 (5)1.11893 (17)0.0748 (16)
H20.22260.71481.12230.090*
C30.3932 (8)0.6864 (6)1.15252 (19)0.088 (2)
H30.37140.71361.17830.106*
C40.5159 (7)0.6437 (6)1.14746 (18)0.0829 (18)
H40.57670.64311.17000.099*
C50.5483 (5)0.6028 (6)1.10994 (16)0.0698 (15)
H50.63040.57261.10720.084*
C60.4601 (5)0.6057 (5)1.07583 (15)0.0581 (13)
C70.2416 (5)0.6562 (5)1.04446 (17)0.0576 (13)
H70.16040.68721.04820.069*
C80.1693 (5)0.6312 (5)0.97399 (15)0.0566 (13)
H80.09120.66810.98360.068*
C90.1432 (5)0.4880 (5)0.95584 (16)0.0632 (14)
H9A0.22280.44430.95100.076*
H9B0.10310.43130.97550.076*
C100.0583 (5)0.4942 (5)0.91573 (16)0.0672 (15)
H10A0.04830.40150.90430.081*
H10B0.02480.52750.92120.081*
C110.1222 (5)0.7256 (5)0.90270 (16)0.0621 (14)
H11A0.03980.75860.90900.075*
H11B0.15270.78760.88240.075*
C120.2130 (5)0.7276 (5)0.94143 (15)0.0601 (14)
H12A0.21950.82140.95220.072*
H12B0.29650.69930.93480.072*
C130.0265 (5)0.5833 (6)0.84734 (17)0.0780 (17)
H13A0.05630.61710.85290.094*
H13B0.01640.48790.83810.094*
C140.0717 (5)0.6680 (6)0.81311 (17)0.0674 (15)
C150.0101 (6)0.7503 (7)0.7894 (2)0.094 (2)
H150.09430.75480.79500.113*
C160.0286 (8)0.8274 (8)0.7570 (2)0.112 (3)
H160.02950.88270.74130.134*
C170.1515 (8)0.8224 (8)0.74818 (19)0.100 (2)
H170.17790.87380.72640.121*
C180.2346 (7)0.7413 (9)0.7715 (2)0.114 (3)
H180.31880.73750.76590.137*
C190.1952 (7)0.6646 (8)0.8034 (2)0.095 (2)
H190.25350.60880.81890.114*
C200.8513 (5)0.8847 (5)1.08785 (16)0.0553 (13)
C210.8191 (6)0.8677 (6)1.12796 (18)0.0803 (17)
H210.73700.84101.13210.096*
C220.9048 (7)0.8893 (8)1.1613 (2)0.100 (2)
H220.88150.87671.18780.120*
C231.0274 (6)0.9302 (6)1.15529 (19)0.0836 (18)
H231.08650.94471.17790.100*
C241.0607 (5)0.9488 (6)1.11692 (18)0.0693 (15)
H241.14270.97721.11340.083*
C250.9754 (5)0.9267 (5)1.08249 (16)0.0564 (13)
C260.7581 (5)0.8606 (5)1.05304 (16)0.0573 (13)
H260.67730.83131.05780.069*
C270.6858 (5)0.8565 (5)0.98220 (15)0.0605 (14)
H270.61280.81000.99240.073*
C280.6448 (5)0.9970 (5)0.96375 (16)0.0632 (14)
H28A0.60561.05150.98410.076*
H28B0.71851.04720.95630.076*
C290.5523 (5)0.9782 (5)0.92612 (17)0.0661 (15)
H29A0.47670.93240.93390.079*
H29B0.52781.06840.91480.079*
C300.6422 (5)0.7581 (5)0.91122 (16)0.0694 (15)
H30A0.67890.70400.89030.083*
H30B0.56690.71020.91830.083*
C310.7362 (5)0.7691 (5)0.94894 (16)0.0682 (15)
H31A0.81420.80990.94130.082*
H31B0.75570.67680.95970.082*
C320.5155 (5)0.8848 (6)0.85825 (17)0.0768 (16)
H32A0.48210.97660.85140.092*
H32B0.44530.82720.86500.092*
C330.5680 (5)0.8258 (6)0.82132 (17)0.0676 (15)
C340.5566 (6)0.6876 (7)0.8109 (2)0.0862 (18)
H340.51680.62840.82810.103*
C350.6009 (7)0.6343 (8)0.7766 (2)0.099 (2)
H350.59300.53980.77110.119*
C360.6567 (7)0.7187 (10)0.7504 (2)0.102 (2)
H360.68470.68270.72640.122*
C370.6717 (7)0.8574 (9)0.7594 (2)0.103 (2)
H370.71100.91570.74170.123*
C380.6278 (6)0.9096 (7)0.7950 (2)0.0878 (19)
H380.63901.00320.80130.105*
N10.2660 (4)0.6217 (4)1.00875 (13)0.0562 (11)
N20.1097 (4)0.5853 (4)0.88561 (12)0.0586 (11)
N30.7836 (4)0.8785 (4)1.01623 (13)0.0578 (11)
N40.6071 (4)0.8956 (4)0.89468 (13)0.0597 (11)
O10.4961 (4)0.5668 (4)1.03919 (12)0.0746 (11)
O21.0116 (4)0.9462 (4)1.04478 (12)0.0777 (12)
H2A0.937 (7)0.915 (7)1.023 (2)0.14 (3)*
H10.424 (7)0.574 (8)1.017 (2)0.15 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.072 (4)0.037 (3)0.060 (3)0.002 (2)0.016 (3)0.001 (2)
C20.102 (5)0.061 (4)0.065 (4)0.009 (3)0.024 (4)0.001 (3)
C30.133 (6)0.067 (4)0.066 (4)0.003 (4)0.019 (4)0.013 (3)
C40.109 (5)0.075 (4)0.062 (4)0.018 (4)0.009 (4)0.003 (3)
C50.082 (4)0.068 (4)0.059 (3)0.013 (3)0.003 (3)0.004 (3)
C60.074 (4)0.047 (3)0.054 (3)0.011 (3)0.007 (3)0.003 (2)
C70.058 (3)0.039 (3)0.078 (4)0.001 (2)0.016 (3)0.007 (3)
C80.054 (3)0.047 (3)0.069 (3)0.007 (2)0.008 (3)0.005 (3)
C90.063 (3)0.041 (3)0.086 (4)0.002 (2)0.007 (3)0.010 (3)
C100.066 (3)0.047 (3)0.087 (4)0.005 (3)0.000 (3)0.008 (3)
C110.069 (3)0.041 (3)0.077 (4)0.004 (3)0.004 (3)0.006 (3)
C120.073 (4)0.036 (3)0.071 (3)0.007 (2)0.004 (3)0.000 (2)
C130.075 (4)0.069 (4)0.086 (4)0.009 (3)0.011 (3)0.005 (3)
C140.067 (4)0.066 (4)0.066 (3)0.004 (3)0.005 (3)0.005 (3)
C150.070 (4)0.114 (6)0.094 (5)0.011 (4)0.010 (4)0.017 (4)
C160.114 (7)0.134 (7)0.084 (5)0.015 (5)0.007 (4)0.035 (5)
C170.104 (6)0.129 (6)0.067 (4)0.009 (5)0.003 (4)0.009 (4)
C180.085 (5)0.163 (8)0.094 (5)0.009 (5)0.011 (4)0.012 (5)
C190.088 (5)0.115 (6)0.082 (4)0.028 (4)0.003 (4)0.015 (4)
C200.060 (3)0.040 (3)0.068 (3)0.003 (2)0.014 (3)0.005 (2)
C210.074 (4)0.091 (4)0.079 (4)0.013 (3)0.020 (3)0.005 (4)
C220.107 (6)0.122 (6)0.072 (4)0.023 (5)0.014 (4)0.010 (4)
C230.092 (5)0.087 (5)0.070 (4)0.002 (4)0.002 (3)0.005 (3)
C240.064 (4)0.065 (4)0.078 (4)0.008 (3)0.005 (3)0.013 (3)
C250.061 (3)0.045 (3)0.065 (3)0.008 (2)0.014 (3)0.009 (2)
C260.060 (3)0.038 (3)0.077 (4)0.002 (2)0.022 (3)0.003 (3)
C270.066 (3)0.047 (3)0.070 (3)0.009 (3)0.014 (3)0.002 (3)
C280.062 (3)0.047 (3)0.081 (4)0.002 (3)0.013 (3)0.004 (3)
C290.058 (3)0.049 (3)0.093 (4)0.009 (3)0.014 (3)0.002 (3)
C300.085 (4)0.049 (3)0.075 (4)0.005 (3)0.007 (3)0.005 (3)
C310.084 (4)0.043 (3)0.077 (4)0.011 (3)0.007 (3)0.002 (3)
C320.065 (4)0.076 (4)0.088 (4)0.010 (3)0.001 (3)0.001 (3)
C330.064 (4)0.063 (4)0.073 (4)0.003 (3)0.009 (3)0.003 (3)
C340.089 (5)0.076 (4)0.094 (5)0.003 (4)0.008 (4)0.008 (4)
C350.103 (6)0.096 (5)0.095 (5)0.012 (4)0.004 (4)0.013 (5)
C360.092 (5)0.140 (7)0.070 (4)0.032 (5)0.005 (4)0.012 (5)
C370.106 (6)0.123 (7)0.078 (5)0.008 (5)0.003 (4)0.028 (5)
C380.092 (5)0.076 (4)0.091 (5)0.002 (4)0.013 (4)0.007 (4)
N10.058 (3)0.049 (2)0.063 (3)0.004 (2)0.010 (2)0.002 (2)
N20.065 (3)0.041 (2)0.068 (3)0.004 (2)0.005 (2)0.000 (2)
N30.058 (3)0.049 (2)0.069 (3)0.003 (2)0.016 (2)0.000 (2)
N40.056 (3)0.047 (2)0.075 (3)0.007 (2)0.004 (2)0.001 (2)
O10.065 (2)0.101 (3)0.059 (2)0.006 (2)0.010 (2)0.011 (2)
O20.062 (2)0.101 (3)0.072 (3)0.010 (2)0.019 (2)0.008 (2)
Geometric parameters (Å, º) top
C1—C21.386 (7)C20—C251.404 (6)
C1—C61.409 (7)C20—C261.449 (7)
C1—C71.453 (7)C21—C221.362 (8)
C2—C31.368 (8)C21—H210.9300
C2—H20.9300C22—C231.390 (8)
C3—C41.389 (8)C22—H220.9300
C3—H30.9300C23—C241.344 (7)
C4—C51.361 (7)C23—H230.9300
C4—H40.9300C24—C251.387 (7)
C5—C61.381 (7)C24—H240.9300
C5—H50.9300C25—O21.336 (6)
C6—O11.342 (6)C26—N31.267 (6)
C7—N11.262 (6)C26—H260.9300
C7—H70.9300C27—N31.458 (6)
C8—N11.455 (6)C27—C311.511 (7)
C8—C91.516 (7)C27—C281.527 (7)
C8—C121.517 (6)C27—H270.9800
C8—H80.9800C28—C291.504 (7)
C9—C101.514 (7)C28—H28A0.9700
C9—H9A0.9700C28—H28B0.9700
C9—H9B0.9700C29—N41.462 (6)
C10—N21.461 (6)C29—H29A0.9700
C10—H10A0.9700C29—H29B0.9700
C10—H10B0.9700C30—N41.464 (6)
C11—N21.462 (6)C30—C311.509 (7)
C11—C121.512 (6)C30—H30A0.9700
C11—H11A0.9700C30—H30B0.9700
C11—H11B0.9700C31—H31A0.9700
C12—H12A0.9700C31—H31B0.9700
C12—H12B0.9700C32—N41.463 (6)
C13—N21.456 (6)C32—C331.487 (7)
C13—C141.498 (7)C32—H32A0.9700
C13—H13A0.9700C32—H32B0.9700
C13—H13B0.9700C33—C381.376 (8)
C14—C151.360 (7)C33—C341.377 (8)
C14—C191.377 (8)C34—C351.353 (8)
C15—C161.384 (9)C34—H340.9300
C15—H150.9300C35—C361.357 (9)
C16—C171.363 (9)C35—H350.9300
C16—H160.9300C36—C371.374 (10)
C17—C181.355 (9)C36—H360.9300
C17—H170.9300C37—C381.388 (9)
C18—C191.372 (9)C37—H370.9300
C18—H180.9300C38—H380.9300
C19—H190.9300O1—H11.01 (8)
C20—C211.393 (7)O2—H2A1.05 (7)
C2—C1—C6118.1 (5)C20—C21—H21119.2
C2—C1—C7121.2 (5)C21—C22—C23119.4 (6)
C6—C1—C7120.7 (5)C21—C22—H22120.3
C3—C2—C1121.9 (6)C23—C22—H22120.3
C3—C2—H2119.0C24—C23—C22120.2 (6)
C1—C2—H2119.0C24—C23—H23119.9
C2—C3—C4118.8 (6)C22—C23—H23119.9
C2—C3—H3120.6C23—C24—C25121.5 (6)
C4—C3—H3120.6C23—C24—H24119.2
C5—C4—C3120.9 (6)C25—C24—H24119.2
C5—C4—H4119.5O2—C25—C24120.0 (5)
C3—C4—H4119.5O2—C25—C20120.8 (5)
C4—C5—C6120.5 (6)C24—C25—C20119.2 (5)
C4—C5—H5119.8N3—C26—C20121.8 (5)
C6—C5—H5119.8N3—C26—H26119.1
O1—C6—C5118.8 (5)C20—C26—H26119.1
O1—C6—C1121.4 (5)N3—C27—C31110.5 (4)
C5—C6—C1119.7 (5)N3—C27—C28109.0 (4)
N1—C7—C1122.6 (5)C31—C27—C28108.6 (4)
N1—C7—H7118.7N3—C27—H27109.6
C1—C7—H7118.7C31—C27—H27109.6
N1—C8—C9109.6 (4)C28—C27—H27109.6
N1—C8—C12110.0 (4)C29—C28—C27110.6 (4)
C9—C8—C12109.9 (4)C29—C28—H28A109.5
N1—C8—H8109.1C27—C28—H28A109.5
C9—C8—H8109.1C29—C28—H28B109.5
C12—C8—H8109.1C27—C28—H28B109.5
C10—C9—C8111.8 (4)H28A—C28—H28B108.1
C10—C9—H9A109.3N4—C29—C28111.4 (4)
C8—C9—H9A109.3N4—C29—H29A109.3
C10—C9—H9B109.3C28—C29—H29A109.3
C8—C9—H9B109.3N4—C29—H29B109.3
H9A—C9—H9B107.9C28—C29—H29B109.3
N2—C10—C9112.0 (4)H29A—C29—H29B108.0
N2—C10—H10A109.2N4—C30—C31111.1 (4)
C9—C10—H10A109.2N4—C30—H30A109.4
N2—C10—H10B109.2C31—C30—H30A109.4
C9—C10—H10B109.2N4—C30—H30B109.4
H10A—C10—H10B107.9C31—C30—H30B109.4
N2—C11—C12110.9 (4)H30A—C30—H30B108.0
N2—C11—H11A109.5C30—C31—C27111.8 (4)
C12—C11—H11A109.5C30—C31—H31A109.3
N2—C11—H11B109.5C27—C31—H31A109.3
C12—C11—H11B109.5C30—C31—H31B109.3
H11A—C11—H11B108.1C27—C31—H31B109.3
C11—C12—C8111.3 (4)H31A—C31—H31B107.9
C11—C12—H12A109.4N4—C32—C33114.4 (4)
C8—C12—H12A109.4N4—C32—H32A108.7
C11—C12—H12B109.4C33—C32—H32A108.7
C8—C12—H12B109.4N4—C32—H32B108.7
H12A—C12—H12B108.0C33—C32—H32B108.7
N2—C13—C14114.8 (5)H32A—C32—H32B107.6
N2—C13—H13A108.6C38—C33—C34116.6 (6)
C14—C13—H13A108.6C38—C33—C32120.8 (6)
N2—C13—H13B108.6C34—C33—C32122.6 (6)
C14—C13—H13B108.6C35—C34—C33122.8 (7)
H13A—C13—H13B107.5C35—C34—H34118.6
C15—C14—C19116.8 (6)C33—C34—H34118.6
C15—C14—C13120.6 (6)C34—C35—C36120.0 (7)
C19—C14—C13122.6 (5)C34—C35—H35120.0
C14—C15—C16121.7 (7)C36—C35—H35120.0
C14—C15—H15119.1C35—C36—C37119.8 (7)
C16—C15—H15119.1C35—C36—H36120.1
C17—C16—C15120.2 (7)C37—C36—H36120.1
C17—C16—H16119.9C36—C37—C38119.3 (7)
C15—C16—H16119.9C36—C37—H37120.4
C18—C17—C16119.0 (7)C38—C37—H37120.4
C18—C17—H17120.5C33—C38—C37121.5 (7)
C16—C17—H17120.5C33—C38—H38119.3
C17—C18—C19120.4 (7)C37—C38—H38119.3
C17—C18—H18119.8C7—N1—C8120.6 (4)
C19—C18—H18119.8C13—N2—C10109.5 (4)
C18—C19—C14121.8 (6)C13—N2—C11111.3 (4)
C18—C19—H19119.1C10—N2—C11109.0 (4)
C14—C19—H19119.1C26—N3—C27119.9 (4)
C21—C20—C25118.0 (5)C29—N4—C32109.3 (4)
C21—C20—C26120.4 (5)C29—N4—C30109.8 (4)
C25—C20—C26121.7 (5)C32—N4—C30111.1 (4)
C22—C21—C20121.7 (6)C6—O1—H1111 (4)
C22—C21—H21119.2C25—O2—H2A109 (4)
C6—C1—C2—C31.4 (8)C21—C20—C25—C240.3 (7)
C7—C1—C2—C3177.8 (5)C26—C20—C25—C24179.7 (5)
C1—C2—C3—C41.0 (9)C21—C20—C26—N3178.2 (5)
C2—C3—C4—C50.5 (9)C25—C20—C26—N31.1 (7)
C3—C4—C5—C61.4 (9)N3—C27—C28—C29174.9 (4)
C4—C5—C6—O1178.9 (5)C31—C27—C28—C2954.5 (6)
C4—C5—C6—C10.9 (8)C27—C28—C29—N458.7 (6)
C2—C1—C6—O1179.7 (5)N4—C30—C31—C2757.2 (6)
C7—C1—C6—O11.1 (7)N3—C27—C31—C30173.5 (4)
C2—C1—C6—C50.5 (7)C28—C27—C31—C3054.0 (6)
C7—C1—C6—C5178.7 (5)N4—C32—C33—C3885.8 (7)
C2—C1—C7—N1179.7 (5)N4—C32—C33—C3496.1 (7)
C6—C1—C7—N11.2 (7)C38—C33—C34—C350.1 (9)
N1—C8—C9—C10171.3 (4)C32—C33—C34—C35178.0 (6)
C12—C8—C9—C1050.2 (6)C33—C34—C35—C361.6 (10)
C8—C9—C10—N255.4 (6)C34—C35—C36—C372.1 (11)
N2—C11—C12—C858.8 (6)C35—C36—C37—C380.9 (11)
N1—C8—C12—C11172.8 (4)C34—C33—C38—C371.4 (9)
C9—C8—C12—C1152.1 (5)C32—C33—C38—C37176.8 (5)
N2—C13—C14—C15136.4 (6)C36—C37—C38—C330.9 (10)
N2—C13—C14—C1945.2 (8)C1—C7—N1—C8179.5 (4)
C19—C14—C15—C160.2 (10)C9—C8—N1—C7118.2 (5)
C13—C14—C15—C16178.7 (6)C12—C8—N1—C7120.8 (5)
C14—C15—C16—C170.0 (12)C14—C13—N2—C10177.4 (5)
C15—C16—C17—C180.1 (12)C14—C13—N2—C1162.1 (6)
C16—C17—C18—C190.5 (12)C9—C10—N2—C13178.0 (4)
C17—C18—C19—C140.7 (12)C9—C10—N2—C1160.0 (5)
C15—C14—C19—C180.6 (10)C12—C11—N2—C13177.6 (4)
C13—C14—C19—C18179.0 (6)C12—C11—N2—C1061.6 (5)
C25—C20—C21—C220.8 (9)C20—C26—N3—C27178.4 (4)
C26—C20—C21—C22179.9 (6)C31—C27—N3—C26132.8 (5)
C20—C21—C22—C230.5 (11)C28—C27—N3—C26107.9 (5)
C21—C22—C23—C240.3 (10)C28—C29—N4—C32177.8 (4)
C22—C23—C24—C250.7 (9)C28—C29—N4—C3060.1 (5)
C23—C24—C25—O2180.0 (5)C33—C32—N4—C29169.3 (5)
C23—C24—C25—C200.4 (8)C33—C32—N4—C3069.5 (6)
C21—C20—C25—O2179.3 (5)C31—C30—N4—C2958.7 (6)
C26—C20—C25—O20.1 (7)C31—C30—N4—C32179.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N11.01 (8)1.73 (7)2.597 (5)141 (6)
O2—H2A···N31.05 (7)1.66 (7)2.588 (6)144 (5)
O1—H1···O1i1.01 (8)2.49 (7)2.869 (7)102 (5)
Symmetry code: (i) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC19H22N2O
Mr294.39
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)10.603 (2), 9.6330 (19), 32.595 (7)
β (°) 95.60 (3)
V3)3313.3 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.40 × 0.40 × 0.20
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.971, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
6837, 6473, 2764
Rint0.117
(sin θ/λ)max1)0.616
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.082, 0.268, 1.09
No. of reflections6473
No. of parameters406
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.20

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N11.01 (8)1.73 (7)2.597 (5)141 (6)
O2—H2A···N31.05 (7)1.66 (7)2.588 (6)144 (5)
O1—H1···O1i1.01 (8)2.49 (7)2.869 (7)102 (5)
Symmetry code: (i) x+1, y+1, z+2.
 

Acknowledgements

We are grateful to the China Postdoctoral Science Foundation (20110491380) and the Fundamental Research Funds for the Central Universities (ZYGX2009J085) for support.

References

First citationEnraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationStilinovic, V., Cincic, D. & Kaitner, B. (2008). Acta. Chim. Solv. 55, 874–879.  CAS

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