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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2006.
Published online 2010 July 14. doi:  10.1107/S1600536810026152
PMCID: PMC3007212

3-[(2-Hy­droxy-1-naphth­yl)(pyrrolidin-1-yl)meth­yl]benzonitrile

Abstract

The title compound, C22H20N2O, was obtained from the condensation reaction of 3-formyl­benzonitrile, 2-naphthol and pyrrolidine. There are two mol­ecules in the asymmetric unit, having similar conformations. Intra­molecular O—H(...)N and C—H(...)O hydrogen bonds occur, with only van der Waals forces between mol­ecules. The dihedral angles between the naphthalene ring system and the phenyl ring in the two molecules are 75.28 (10) and 76.07 (11)°. The five-membered rings adopt half-chair conformations.

Related literature

For the applications of Betti-type reactions, see: Lu et al. (2002 [triangle]); Xu et al. (2004 [triangle]); Wang et al. (2005 [triangle]).

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Object name is e-66-o2006-scheme1.jpg

Experimental

Crystal data

  • C22H20N2O
  • M r = 328.40
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2006-efi1.jpg
  • a = 18.735 (4) Å
  • b = 10.475 (2) Å
  • c = 18.122 (4) Å
  • V = 3556.4 (12) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.20 × 0.20 × 0.20 mm

Data collection

  • Rigaku Mercury2 diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.825, T max = 1.000
  • 31413 measured reflections
  • 3612 independent reflections
  • 2166 reflections with I > 2σ(I)
  • R int = 0.125

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.149
  • S = 1.07
  • 3612 reflections
  • 452 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL/PC (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL/PC.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810026152/rz2464sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026152/rz2464Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the Natural Science Foundation (04KJD150112) of Jiangsu Provincial Education Department.

supplementary crystallographic information

Comment

Over one hundred years ago, Betti developed a straightforward synthesis involving the condensation of 2-naphthol, ammonia and equivalents of benzaldehyde, followed by the addition of HCl and KOH to yield 1-(a-aminobenzyl)-2-naphthol. This product which possesses an asymmetric carbon center is known as a Betti base. Betti-type reaction is an important method to synthesize chiral ligands and by this method many unnatural homochiral amino-phenol compounds have been obtained (Lu et al. 2002; Xu et al. 2004; Wang et al. 2005). Here we report the synthesis and crystal structure of the title compound, 3-[(2-hydroxynaphthalen-1-yl)(pyrrolidin-1-yl)methyl]benzonitrile (Fig. 1).

Both molecules in the asymmetric unit have the same relative conformation at the chiral carbon atoms. The naphthalene (A; C1–C10, B; C23–C32) and benzene (C; C16–C21, D; C34–C39) rings are strictly planar and the dihedral angles between A/C and B/D are 75.28 (10) and 76.07 (11)°, respectively. The two molecules are stabilized by intramolecular O—H···N hydrogen bonding, whereas only one is involved in intramolecular C—H···O hydrogen bonds (Table 1). Intermolecular interactions are only van der Waals forces.

Experimental

3-Formylbenzonitrile (1.97 g, 0.015 mol) and pyrrolidine (1.065 g, 0.015 mol) was added to 2-naphthol (2.16 g, 0.015 mol) without solvent under nitrogen. The temperature was raised gradually to 120°C in one hour and the mixture was stirred at this temperature for 12 h. The system was treated with 30 ml of ethanol 95% and cooled. The precipitate was filtered and washed with a small amount of ethanol 95%. The title compound was isolated using column chromatography (petroleum ether:ethyl acetate 4:1 v/v). Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of an ethyl acetate solution at room temperature.

Refinement

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å, O—H = 0.82 Å, and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(O). In the absence of significant anomalous scattering effects, the 3377 Friedel pairs were merged. The relatively high Rint value and the low data/parameter ratio reflects the poor quality of the crystal.

Figures

Fig. 1.
Perspective structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C22H20N2OF(000) = 1392
Mr = 328.40Dx = 1.227 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 3612 reflections
a = 18.735 (4) Åθ = 2.6–26.0°
b = 10.475 (2) ŵ = 0.08 mm1
c = 18.122 (4) ÅT = 293 K
V = 3556.4 (12) Å3Prism, colourless
Z = 80.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer3612 independent reflections
Radiation source: fine-focus sealed tube2166 reflections with I > 2σ(I)
graphiteRint = 0.125
Detector resolution: 13.6612 pixels mm-1θmax = 26.0°, θmin = 3.1°
CCD_Profile_fitting scansh = −23→23
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −12→12
Tmin = 0.825, Tmax = 1.000l = −22→22
31413 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.065P)2 + 0.150P] where P = (Fo2 + 2Fc2)/3
3612 reflections(Δ/σ)max < 0.001
452 parametersΔρmax = 0.16 e Å3
1 restraintΔρmin = −0.16 e Å3

Special details

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)

xyzUiso*/Ueq
O10.99425 (19)0.9948 (4)0.6386 (2)0.0722 (11)
H1A0.98480.92790.61730.108*
O20.1596 (2)0.5126 (4)0.3506 (2)0.0758 (11)
H2A0.17990.58050.35870.114*
C200.8916 (3)0.9893 (4)0.4063 (3)0.0511 (12)
C340.2940 (2)0.6121 (4)0.4724 (3)0.0481 (11)
C10.8658 (3)1.0060 (5)0.6434 (3)0.0506 (12)
N30.1789 (2)0.7119 (3)0.4331 (2)0.0556 (11)
C170.8022 (3)0.8267 (5)0.4799 (3)0.0613 (13)
H17A0.77170.77070.50440.074*
C160.8526 (2)0.8953 (4)0.5204 (3)0.0478 (11)
N10.9174 (2)0.7925 (4)0.6241 (2)0.0553 (11)
C350.3411 (3)0.6798 (5)0.5162 (3)0.0649 (14)
H35A0.32320.73540.55160.078*
C230.1768 (2)0.4942 (4)0.4814 (3)0.0540 (12)
C210.8972 (2)0.9772 (4)0.4825 (3)0.0511 (12)
H21A0.93121.02450.50810.061*
C330.2139 (2)0.6242 (4)0.4850 (3)0.0512 (12)
H33A0.20680.65830.53480.061*
C20.9328 (3)1.0546 (5)0.6582 (3)0.0560 (13)
C90.8046 (3)1.0760 (5)0.6660 (2)0.0495 (12)
C390.3220 (2)0.5309 (4)0.4191 (3)0.0504 (12)
H39A0.29150.48410.38900.060*
C110.8581 (3)0.8773 (4)0.6034 (3)0.0521 (13)
H11A0.81370.83750.62040.063*
C310.1686 (3)0.4212 (5)0.5466 (3)0.0596 (14)
C220.9394 (3)1.0752 (6)0.3687 (3)0.0764 (17)
C260.1079 (3)0.2602 (6)0.4724 (5)0.084 (2)
H26A0.08420.18250.46890.100*
C420.1570 (3)0.9229 (6)0.3957 (4)0.091 (2)
H42A0.15930.92490.34220.110*
H42B0.16281.00910.41420.110*
C320.1309 (3)0.3015 (5)0.5413 (4)0.0719 (18)
C410.2134 (3)0.8384 (4)0.4258 (3)0.0692 (15)
H41A0.25380.83410.39250.083*
H41B0.22970.86910.47340.083*
C100.8134 (3)1.1955 (5)0.7035 (3)0.0591 (14)
C40.8831 (3)1.2381 (5)0.7176 (3)0.0683 (16)
H4A0.88951.31370.74360.082*
C380.3954 (2)0.5194 (5)0.4108 (3)0.0522 (12)
C30.9407 (3)1.1739 (5)0.6948 (3)0.0665 (15)
H3A0.98601.20720.70300.080*
C120.9237 (3)0.6728 (5)0.5805 (3)0.0701 (16)
H12A0.94320.68940.53180.084*
H12B0.87780.63080.57540.084*
C80.7341 (3)1.0379 (5)0.6519 (3)0.0622 (14)
H8A0.72650.96300.62540.075*
C300.1949 (3)0.4570 (6)0.6151 (4)0.0794 (18)
H30A0.22110.53200.61930.095*
C240.1520 (3)0.4480 (5)0.4139 (4)0.0611 (14)
C440.1058 (3)0.7426 (5)0.4580 (4)0.0766 (17)
H44A0.10420.75140.51120.092*
H44B0.07260.67610.44330.092*
C270.1212 (4)0.2315 (6)0.6069 (6)0.098 (3)
H27A0.09670.15430.60420.118*
C250.1188 (3)0.3286 (5)0.4107 (4)0.0712 (16)
H25A0.10400.29620.36540.085*
C190.8404 (3)0.9221 (5)0.3668 (3)0.0645 (15)
H19A0.83600.93260.31600.077*
C180.7966 (3)0.8401 (5)0.4044 (3)0.0686 (15)
H18A0.76270.79290.37870.082*
C370.4410 (3)0.5868 (5)0.4566 (3)0.0708 (16)
H37A0.49010.57740.45170.085*
C50.7527 (4)1.2623 (5)0.7266 (3)0.0744 (16)
H5A0.75901.33840.75230.089*
C150.9121 (3)0.7469 (5)0.7019 (3)0.0729 (16)
H15A0.86400.71900.71310.088*
H15B0.92560.81380.73620.088*
N20.9776 (4)1.1433 (6)0.3394 (3)0.114 (2)
C280.1449 (5)0.2691 (8)0.6720 (6)0.113 (3)
H28A0.13650.22040.71410.136*
C400.4246 (3)0.4309 (6)0.3597 (4)0.0746 (17)
C60.6855 (4)1.2217 (7)0.7135 (4)0.0821 (18)
H40A0.64641.26910.72940.099*
C70.6758 (3)1.1065 (7)0.6754 (4)0.0794 (18)
H7A0.63001.07640.66610.095*
C130.9750 (4)0.5932 (6)0.6269 (4)0.103 (2)
H13A0.96430.50290.62220.123*
H13B1.02400.60770.61180.123*
N40.4512 (3)0.3616 (7)0.3192 (4)0.119 (2)
C430.0872 (3)0.8681 (6)0.4207 (5)0.103 (2)
H43A0.05580.85390.37890.123*
H43B0.06380.92540.45510.123*
C290.1831 (5)0.3845 (8)0.6764 (4)0.111 (3)
H29A0.20060.41170.72170.134*
C140.9633 (4)0.6377 (6)0.7056 (4)0.100 (2)
H14A0.94370.56920.73530.121*
H14B1.00810.66490.72740.121*
C360.4140 (3)0.6667 (5)0.5085 (4)0.0752 (17)
H36A0.44470.71270.53890.090*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.060 (2)0.066 (2)0.090 (3)−0.0146 (19)0.007 (2)−0.011 (2)
O20.081 (3)0.067 (3)0.079 (3)−0.006 (2)−0.009 (2)−0.005 (2)
C200.055 (3)0.046 (3)0.052 (3)0.000 (2)−0.001 (3)0.007 (2)
C340.051 (3)0.041 (3)0.052 (3)−0.006 (2)−0.002 (2)0.001 (2)
C10.055 (3)0.046 (3)0.051 (3)−0.010 (2)0.003 (2)0.000 (2)
N30.053 (2)0.039 (2)0.074 (3)0.0024 (18)0.012 (2)−0.004 (2)
C170.050 (3)0.063 (3)0.071 (4)−0.015 (3)0.003 (3)−0.009 (3)
C160.049 (3)0.043 (3)0.052 (3)−0.004 (2)0.002 (2)−0.009 (2)
N10.065 (3)0.047 (2)0.054 (3)−0.001 (2)−0.002 (2)0.002 (2)
C350.075 (4)0.050 (3)0.070 (4)−0.005 (3)−0.004 (3)−0.011 (3)
C230.047 (3)0.042 (3)0.073 (3)0.001 (2)0.016 (3)−0.001 (3)
C210.050 (3)0.049 (3)0.055 (3)−0.007 (2)0.000 (2)−0.005 (2)
C330.064 (3)0.035 (2)0.055 (3)−0.001 (2)0.012 (3)−0.002 (2)
C20.055 (3)0.054 (3)0.059 (3)−0.009 (3)0.010 (3)−0.001 (2)
C90.059 (3)0.048 (3)0.041 (3)−0.007 (2)0.004 (2)0.002 (2)
C390.052 (3)0.044 (3)0.055 (3)−0.006 (2)0.004 (2)−0.005 (2)
C110.049 (3)0.045 (3)0.062 (3)−0.009 (2)−0.001 (2)0.004 (2)
C310.061 (3)0.041 (3)0.077 (4)0.003 (2)0.023 (3)−0.001 (3)
C220.088 (4)0.084 (5)0.057 (4)−0.013 (4)−0.007 (3)0.006 (3)
C260.046 (3)0.047 (3)0.158 (7)−0.004 (3)0.008 (4)−0.017 (5)
C420.090 (5)0.056 (4)0.129 (6)0.017 (3)0.001 (4)0.007 (4)
C320.052 (3)0.043 (3)0.121 (6)0.005 (3)0.030 (4)0.014 (3)
C410.076 (4)0.042 (3)0.090 (4)−0.003 (3)0.003 (3)0.002 (3)
C100.068 (4)0.052 (3)0.058 (3)−0.002 (3)0.002 (3)0.001 (3)
C40.084 (4)0.056 (3)0.065 (4)−0.018 (3)0.005 (3)−0.010 (3)
C380.047 (3)0.050 (3)0.059 (3)−0.005 (2)0.007 (3)0.004 (3)
C30.069 (4)0.065 (3)0.066 (4)−0.022 (3)0.004 (3)−0.011 (3)
C120.090 (4)0.054 (3)0.067 (4)0.009 (3)−0.009 (3)−0.003 (3)
C80.064 (4)0.057 (3)0.066 (4)−0.004 (3)0.004 (3)0.001 (3)
C300.101 (5)0.058 (4)0.079 (5)0.003 (3)0.026 (4)0.012 (4)
C240.049 (3)0.049 (3)0.085 (4)−0.007 (2)0.005 (3)−0.015 (3)
C440.063 (3)0.066 (4)0.101 (5)0.005 (3)0.012 (3)0.001 (3)
C270.086 (5)0.049 (4)0.160 (8)0.008 (3)0.048 (5)0.029 (5)
C250.053 (3)0.051 (3)0.110 (5)−0.005 (3)0.000 (3)−0.015 (4)
C190.071 (4)0.064 (4)0.058 (3)0.001 (3)−0.002 (3)−0.005 (3)
C180.070 (4)0.066 (4)0.070 (4)−0.012 (3)−0.010 (3)−0.014 (3)
C370.046 (3)0.070 (4)0.097 (5)−0.007 (3)−0.003 (3)0.000 (3)
C50.094 (5)0.065 (3)0.064 (4)0.006 (4)0.007 (3)−0.007 (3)
C150.096 (4)0.062 (4)0.061 (4)−0.001 (3)−0.011 (3)0.002 (3)
N20.135 (5)0.125 (5)0.083 (4)−0.047 (4)0.015 (4)0.016 (4)
C280.148 (8)0.080 (6)0.112 (7)0.016 (5)0.056 (6)0.050 (5)
C400.045 (3)0.090 (5)0.089 (5)0.003 (3)0.007 (3)−0.012 (4)
C60.084 (5)0.081 (5)0.081 (5)0.026 (4)0.003 (4)−0.002 (4)
C70.060 (4)0.092 (5)0.086 (5)0.007 (4)0.004 (3)0.007 (4)
C130.146 (7)0.076 (4)0.087 (5)0.021 (4)−0.015 (5)0.003 (4)
N40.072 (4)0.150 (6)0.134 (6)0.023 (4)0.011 (4)−0.041 (5)
C430.070 (4)0.074 (4)0.164 (7)0.015 (3)0.006 (5)−0.002 (5)
C290.158 (7)0.096 (6)0.081 (5)0.014 (5)0.043 (5)0.018 (4)
C140.136 (6)0.067 (4)0.098 (6)0.013 (4)−0.035 (5)0.008 (4)
C360.071 (4)0.061 (4)0.094 (5)−0.014 (3)−0.014 (3)−0.018 (3)

Geometric parameters (Å, °)

O1—C21.357 (6)C41—H41A0.9700
O1—H1A0.8200C41—H41B0.9700
O2—C241.339 (7)C10—C51.400 (8)
O2—H2A0.8200C10—C41.403 (7)
C20—C191.388 (7)C4—C31.336 (8)
C20—C211.391 (7)C4—H4A0.9300
C20—C221.441 (8)C38—C371.384 (7)
C34—C351.382 (7)C38—C401.419 (8)
C34—C391.389 (7)C3—H3A0.9300
C34—C331.523 (6)C12—C131.526 (8)
C1—C21.381 (7)C12—H12A0.9700
C1—C91.421 (7)C12—H12B0.9700
C1—C111.537 (7)C8—C71.376 (8)
N3—C331.469 (6)C8—H8A0.9300
N3—C441.477 (6)C30—C291.363 (9)
N3—C411.481 (6)C30—H30A0.9300
C17—C181.381 (8)C24—C251.399 (7)
C17—C161.395 (7)C44—C431.519 (8)
C17—H17A0.9300C44—H44A0.9700
C16—C211.381 (6)C44—H44B0.9700
C16—C111.520 (7)C27—C281.322 (11)
N1—C111.471 (6)C27—H27A0.9300
N1—C121.487 (6)C25—H25A0.9300
N1—C151.491 (7)C19—C181.369 (8)
C35—C361.381 (7)C19—H19A0.9300
C35—H35A0.9300C18—H18A0.9300
C23—C241.395 (8)C37—C361.357 (8)
C23—C311.415 (7)C37—H37A0.9300
C23—C331.531 (6)C5—C61.351 (9)
C21—H21A0.9300C5—H5A0.9300
C33—H33A0.9800C15—C141.494 (8)
C2—C31.423 (7)C15—H15A0.9700
C9—C81.403 (7)C15—H15B0.9700
C9—C101.433 (7)C28—C291.408 (12)
C39—C381.389 (6)C28—H28A0.9300
C39—H39A0.9300C40—N41.147 (7)
C11—H11A0.9800C6—C71.402 (9)
C31—C301.388 (8)C6—H40A0.9300
C31—C321.442 (8)C7—H7A0.9300
C22—N21.142 (7)C13—C141.516 (9)
C26—C251.343 (9)C13—H13A0.9700
C26—C321.389 (9)C13—H13B0.9700
C26—H26A0.9300C43—H43A0.9700
C42—C411.482 (8)C43—H43B0.9700
C42—C431.497 (9)C29—H29A0.9300
C42—H42A0.9700C14—H14A0.9700
C42—H42B0.9700C14—H14B0.9700
C32—C271.409 (10)C36—H36A0.9300
C2—O1—H1A109.5C39—C38—C40120.6 (5)
C24—O2—H2A109.5C4—C3—C2120.1 (5)
C19—C20—C21121.3 (5)C4—C3—H3A119.9
C19—C20—C22120.1 (5)C2—C3—H3A119.9
C21—C20—C22118.6 (5)N1—C12—C13102.5 (4)
C35—C34—C39118.2 (4)N1—C12—H12A111.3
C35—C34—C33120.0 (4)C13—C12—H12A111.3
C39—C34—C33121.8 (4)N1—C12—H12B111.3
C2—C1—C9119.1 (4)C13—C12—H12B111.3
C2—C1—C11120.0 (4)H12A—C12—H12B109.2
C9—C1—C11120.9 (4)C7—C8—C9122.8 (5)
C33—N3—C44110.8 (4)C7—C8—H8A118.6
C33—N3—C41114.9 (4)C9—C8—H8A118.6
C44—N3—C41103.7 (4)C29—C30—C31121.4 (7)
C18—C17—C16121.3 (5)C29—C30—H30A119.3
C18—C17—H17A119.3C31—C30—H30A119.3
C16—C17—H17A119.3O2—C24—C23122.8 (4)
C21—C16—C17118.0 (5)O2—C24—C25117.6 (6)
C21—C16—C11121.9 (4)C23—C24—C25119.7 (6)
C17—C16—C11120.2 (4)N3—C44—C43105.3 (5)
C11—N1—C12115.7 (4)N3—C44—H44A110.7
C11—N1—C15112.6 (4)C43—C44—H44A110.7
C12—N1—C15103.7 (4)N3—C44—H44B110.7
C36—C35—C34121.5 (5)C43—C44—H44B110.7
C36—C35—H35A119.2H44A—C44—H44B108.8
C34—C35—H35A119.2C28—C27—C32123.7 (7)
C24—C23—C31120.5 (5)C28—C27—H27A118.1
C24—C23—C33119.8 (5)C32—C27—H27A118.1
C31—C23—C33119.7 (5)C26—C25—C24120.6 (6)
C16—C21—C20120.3 (5)C26—C25—H25A119.7
C16—C21—H21A119.9C24—C25—H25A119.7
C20—C21—H21A119.9C18—C19—C20118.4 (5)
N3—C33—C34113.3 (4)C18—C19—H19A120.8
N3—C33—C23109.1 (4)C20—C19—H19A120.8
C34—C33—C23111.5 (4)C19—C18—C17120.8 (5)
N3—C33—H33A107.6C19—C18—H18A119.6
C34—C33—H33A107.6C17—C18—H18A119.6
C23—C33—H33A107.6C36—C37—C38120.1 (5)
O1—C2—C1123.4 (4)C36—C37—H37A120.0
O1—C2—C3116.0 (5)C38—C37—H37A120.0
C1—C2—C3120.6 (5)C6—C5—C10123.2 (6)
C8—C9—C1124.0 (4)C6—C5—H5A118.4
C8—C9—C10116.3 (5)C10—C5—H5A118.4
C1—C9—C10119.7 (4)N1—C15—C14104.2 (5)
C34—C39—C38120.1 (4)N1—C15—H15A110.9
C34—C39—H39A119.9C14—C15—H15A110.9
C38—C39—H39A119.9N1—C15—H15B110.9
N1—C11—C16112.2 (4)C14—C15—H15B110.9
N1—C11—C1109.8 (4)H15A—C15—H15B108.9
C16—C11—C1111.4 (4)C27—C28—C29118.5 (7)
N1—C11—H11A107.7C27—C28—H28A120.8
C16—C11—H11A107.7C29—C28—H28A120.8
C1—C11—H11A107.7N4—C40—C38176.9 (6)
C30—C31—C23124.2 (5)C5—C6—C7118.6 (6)
C30—C31—C32117.9 (6)C5—C6—H40A120.7
C23—C31—C32117.8 (6)C7—C6—H40A120.7
N2—C22—C20179.4 (7)C8—C7—C6119.9 (6)
C25—C26—C32122.4 (5)C8—C7—H7A120.0
C25—C26—H26A118.8C6—C7—H7A120.0
C32—C26—H26A118.8C14—C13—C12105.1 (5)
C41—C42—C43106.4 (5)C14—C13—H13A110.7
C41—C42—H42A110.4C12—C13—H13A110.7
C43—C42—H42A110.4C14—C13—H13B110.7
C41—C42—H42B110.4C12—C13—H13B110.7
C43—C42—H42B110.4H13A—C13—H13B108.8
H42A—C42—H42B108.6C42—C43—C44105.4 (5)
C26—C32—C27123.8 (7)C42—C43—H43A110.7
C26—C32—C31118.8 (6)C44—C43—H43A110.7
C27—C32—C31117.4 (7)C42—C43—H43B110.7
N3—C41—C42104.8 (4)C44—C43—H43B110.7
N3—C41—H41A110.8H43A—C43—H43B108.8
C42—C41—H41A110.8C30—C29—C28121.1 (8)
N3—C41—H41B110.8C30—C29—H29A119.5
C42—C41—H41B110.8C28—C29—H29A119.5
H41A—C41—H41B108.9C15—C14—C13106.6 (5)
C5—C10—C4122.9 (5)C15—C14—H14A110.4
C5—C10—C9119.0 (5)C13—C14—H14A110.4
C4—C10—C9118.1 (5)C15—C14—H14B110.4
C3—C4—C10122.4 (5)C13—C14—H14B110.4
C3—C4—H4A118.8H14A—C14—H14B108.6
C10—C4—H4A118.8C37—C36—C35120.0 (5)
C37—C38—C39120.1 (5)C37—C36—H36A120.0
C37—C38—C40119.1 (5)C35—C36—H36A120.0

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.821.902.576 (5)139
O2—H2A···N30.821.932.593 (5)138
C39—H39A···O20.932.583.292 (6)133

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2464).

References

  • Lu, J., Xu, X. N., Wang, C. D., He, J. G., Hu, Y. F. & Hu, H. W. (2002). Tetrahedron Lett.43, 8367–8369.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, X. Y., Dong, Y. M., Sun, J. W., Xu, X. N., Li, R. & Hu, Y. F. (2005). J. Org. Chem.70, 1897–1900. [PubMed]
  • Xu, X. N., Lu, J., Dong, Y. M., Li, R., Ge, Z. M. & Hu, Y. F. (2004). Tetrahedron Asymmetry, 15, 475–479.

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