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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1035.
Published online 2009 April 18. doi:  10.1107/S1600536809011817
PMCID: PMC2977718

(+)-[1-(4-Methoxy­benz­yl)pyrrolidin-2-yl]diphenyl­methanol

Abstract

The title compound, C25H27NO2, was obtained as the product of a Grignard reagent and an inter­mediate ester synthesized from L-(-)-proline. The asymmetric unit contains two independent mol­ecules, both of which feature an intra­molecular O—H(...)N hydrogen bond. In one of the mol­ecules, the pyrrolidine ring is disordered over two orientations in a 0.63 (3):0.37 (3) ratio.

Related literature

For the synthesis, see: Baker et al. (1991 [triangle]); Zhao et al. (1999 [triangle]). For background on the applications of this family of compounds, see: Kagabu et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1035-scheme1.jpg

Experimental

Crystal data

  • C25H27NO2
  • M r = 373.48
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1035-efi1.jpg
  • a = 33.131 (4) Å
  • b = 5.9916 (7) Å
  • c = 21.472 (3) Å
  • β = 97.715 (3)°
  • V = 4223.8 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 292 K
  • 0.20 × 0.10 × 0.04 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: none
  • 20497 measured reflections
  • 4093 independent reflections
  • 2040 reflections with I > 2σ(I)
  • R int = 0.107

Refinement

  • R[F 2 > 2σ(F 2)] = 0.067
  • wR(F 2) = 0.179
  • S = 0.93
  • 4093 reflections
  • 536 parameters
  • 7 restraints
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011817/hb2936sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011817/hb2936Isup2.hkl

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

Acknowledgments

This research was supported by the National Natural Science Foundation of China (No. 20672073) and Shanghai Key Laboratory of Lanthanide Functional Materials (No. 07dz22303)

supplementary crystallographic information

Comment

Pyrrolidine derivatives have received much attention on their potential applications in chiral catalysis, medicine intermediate and pesticide (e.g. Kagabu et al., 2007). We report here the synthesis and crystal structure of the title compound (I).

There are four aromatic rings in one molecule structure (Figure 1), namely a pyrrolidine ring (N2/C39—C42), phenyl rings (C26—C31), (C32—C37), (C44—C49) (Fig 1). the phenyl ring (C26—C31) and phenyl ring (C32—C37) forms dihedral angle of 71.5 (8)°; the phenyl ring (C32—C37) and phenyl ring (C44—C49) forms dihedral angle of 83.4 (6)°; the phenyl ring (C26—C31) and phenyl ring (C44—C49) forms dihedral angle of 41.1 (6)°. It is interesting that the dihedral angle of the phenyl ring (C26—C31) and phenyl ring (C44—C49) are smaller than the other two dihedral angles. It probably because that the —OCH3 effect the phenyl ring (C44—C49). Another structure feature that should be mentioned here is the N—C bond length data (C18—N1 1.45 Å and C43—N2 1.45 Å) in the crystal of compound (I) are between the standard C—N (1.47 Å) and C=N (1.26 Å), which shows that the nitrogen atom may have weak conjugation with the carbon atom (C18 and C43).

The title compound (I) belongs to monoclinic crystal system with space group C2. Each asymmetric unit contains two independent conformational isomer molecules, and two intramolecular hydrogen bonds (O3—H3A···N2) and (O1—H1···N1) are observed (Table 1) forming two five-membered rings (O1, H1, N1, C13, C14) and (O3, H3A, N2, C38, C39).

Experimental

The title compound was prepared by the literature method (Zhao et al., 1999; Baker et al., 1991) and crystals were grown using volatilization of dichloromethane and methanol solution at room temperature. 1H NMR (DMSO-d6, 400 MHz): 6.67–7.66 (m, 14H, Ph—H), 4.95(s, 1H, —OH),3.95(m, 1H, pyrrol N—H), 3.61(s, 3H, —OCH3), 2.95(m, 2H, CH2), 2.69(m, 1H, pyrrol N—H), 2.17(m, 1H, pyrrol N—H), 1.78(m, 1H, pyrrol N—H), 1.45(m, 3H, pyrrol N—H); Analysis calculated for C25H27NO2: C 80.61, H 7.04, N 3.76%; found: C 80.40, H 7.29, N 3.75%. Colourless plates of (I) suitable for single-crystal X-ray diffraction were selected directly from the sample as prepared.

Refinement

Anomalous dispersion was negligible and Friedel pairs were merged before refinement. The H atoms were placed in idealised locations (C—H = 0.93–0.98Å, O—H = 0.82Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C, O).

Figures

Fig. 1.
The molecular structure of the N2 molecule (I), showing 30% displacement ellipsoids for the non-hydrogen atoms. The hydrogen bond is shown as a double dashed line.
Fig. 2.
Supplementary figure.

Crystal data

C25H27NO2F(000) = 1600
Mr = 373.48Dx = 1.175 Mg m3
Monoclinic, C2Melting point: 391 K
Hall symbol: C 2yMo Kα radiation, λ = 0.71073 Å
a = 33.131 (4) ÅCell parameters from 1185 reflections
b = 5.9916 (7) Åθ = 2.5–17.0°
c = 21.472 (3) ŵ = 0.07 mm1
β = 97.715 (3)°T = 292 K
V = 4223.8 (9) Å3Plate, colourless
Z = 80.20 × 0.10 × 0.04 mm

Data collection

Bruker SMART CCD diffractometer2040 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.107
graphiteθmax = 25.0°, θmin = 1.7°
ω scansh = −39→39
20497 measured reflectionsk = −7→7
4093 independent reflectionsl = −25→25

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.179w = 1/[σ2(Fo2) + (0.0935P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max < 0.001
4093 reflectionsΔρmax = 0.19 e Å3
536 parametersΔρmin = −0.16 e Å3
7 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0016 (4)

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*/UeqOcc. (<1)
C10.08941 (17)0.3509 (11)0.3865 (3)0.0601 (17)
C20.0964 (2)0.1590 (16)0.4202 (3)0.099 (2)
H20.10870.03830.40300.119*
C30.0852 (3)0.143 (2)0.4800 (4)0.122 (3)
H30.09110.01150.50260.146*
C40.0666 (3)0.303 (2)0.5063 (4)0.112 (3)
H40.05850.28410.54580.135*
C50.0596 (3)0.4983 (19)0.4745 (3)0.114 (3)
H50.04720.61610.49280.136*
C60.0709 (2)0.5235 (14)0.4141 (3)0.097 (3)
H60.06590.65770.39270.117*
C70.04379 (19)0.6188 (11)0.2672 (3)0.0637 (17)
H70.05270.73430.29450.076*
C80.0106 (2)0.6517 (14)0.2239 (3)0.0721 (18)
H8−0.00300.78770.22260.087*
C9−0.0031 (2)0.4887 (18)0.1823 (3)0.088 (2)
H9−0.02570.51260.15230.106*
C100.0170 (2)0.2886 (14)0.1852 (4)0.090 (2)
H100.00790.17550.15710.109*
C110.0506 (2)0.2531 (12)0.2294 (3)0.0760 (19)
H110.06400.11630.23050.091*
C120.06482 (16)0.4176 (10)0.2720 (2)0.0485 (15)
C130.10208 (18)0.3747 (12)0.3204 (3)0.0633 (17)
C140.13520 (17)0.5563 (14)0.3190 (2)0.073 (2)
H140.12370.70680.32010.087*
C170.2001 (3)0.488 (5)0.2787 (6)0.099 (7)0.63 (3)
H17A0.21480.62690.27610.119*0.63 (3)
H17B0.21000.37930.25100.119*0.63 (3)
C160.2048 (4)0.401 (5)0.3470 (5)0.091 (7)0.63 (3)
H16A0.20190.24030.34820.109*0.63 (3)
H16B0.23100.44280.36980.109*0.63 (3)
C150.1699 (8)0.519 (5)0.3738 (15)0.077 (8)0.63 (3)
H15A0.17910.66050.39230.093*0.63 (3)
H15B0.16040.42710.40610.093*0.63 (3)
C15'0.1681 (16)0.600 (12)0.379 (3)0.117 (17)0.37 (3)
H15C0.16320.74120.39860.140*0.37 (3)
H15D0.16810.48110.40930.140*0.37 (3)
C16'0.2083 (9)0.605 (11)0.3506 (11)0.134 (16)0.37 (3)
H16C0.22520.72900.36760.161*0.37 (3)
H16D0.22330.46730.35970.161*0.37 (3)
C17'0.1961 (6)0.633 (6)0.2798 (10)0.089 (10)0.37 (3)
H17C0.19420.78990.26900.107*0.37 (3)
H17D0.21630.56420.25720.107*0.37 (3)
C180.14033 (19)0.6485 (12)0.2070 (3)0.0732 (19)
H18A0.14750.80430.21380.088*
H18B0.11080.63830.20030.088*
C190.15663 (18)0.5684 (12)0.1493 (3)0.0616 (17)
C200.18472 (19)0.6911 (13)0.1207 (3)0.0732 (19)
H200.19330.82960.13690.088*
C210.2001 (2)0.6082 (14)0.0680 (3)0.077 (2)
H210.21960.68950.05050.092*
C220.1868 (2)0.4085 (14)0.0416 (3)0.0696 (19)
C230.15938 (19)0.2875 (12)0.0687 (3)0.0729 (18)
H230.15000.15180.05140.087*
C240.14537 (19)0.3664 (13)0.1223 (3)0.0725 (19)
H240.12740.27790.14120.087*
C250.1898 (2)0.1469 (16)−0.0416 (3)0.110 (3)
H25A0.19580.0253−0.01280.165*
H25B0.20340.1238−0.07780.165*
H25C0.16090.1544−0.05450.165*
C260.33222 (18)0.4931 (11)0.3688 (3)0.0618 (16)
C270.3166 (2)0.6886 (14)0.3858 (4)0.097 (2)
H270.31660.81090.35920.117*
C280.3004 (3)0.7125 (19)0.4421 (5)0.130 (4)
H280.29150.85200.45340.156*
C290.2977 (3)0.545 (2)0.4790 (4)0.117 (3)
H290.28480.55980.51460.140*
C300.3142 (3)0.343 (2)0.4651 (4)0.115 (3)
H300.31420.22370.49280.138*
C310.3311 (2)0.3178 (14)0.4090 (3)0.093 (2)
H310.34160.18030.39910.112*
C320.39796 (18)0.4804 (10)0.3256 (2)0.0550 (15)
C330.4203 (2)0.3095 (12)0.3570 (3)0.0680 (18)
H330.40700.18050.36700.082*
C340.4615 (2)0.3257 (13)0.3735 (3)0.0731 (19)
H340.47560.20960.39530.088*
C350.4820 (2)0.5112 (17)0.3582 (3)0.085 (2)
H350.51010.51970.36890.102*
C360.4613 (2)0.6840 (14)0.3273 (3)0.079 (2)
H360.47540.81060.31750.094*
C370.4193 (2)0.6723 (11)0.3103 (3)0.0661 (18)
H370.40530.79020.28900.079*
C380.35166 (18)0.4709 (10)0.3084 (3)0.0587 (16)
C390.33731 (17)0.2594 (11)0.2707 (2)0.0595 (16)
H390.35120.12780.29040.071*
C400.29109 (17)0.2231 (13)0.2623 (3)0.075 (2)
H40A0.28460.07940.27930.090*
H40B0.27790.33900.28390.090*
C410.2770 (2)0.232 (2)0.1931 (3)0.126 (4)
H41A0.25610.12070.18110.151*
H41B0.26610.37810.18080.151*
C420.3128 (2)0.1855 (15)0.1642 (3)0.093 (2)
H42A0.31040.25130.12260.111*
H42B0.31660.02580.16050.111*
C430.38595 (19)0.1928 (12)0.1945 (2)0.0728 (19)
H43A0.38430.03120.19460.087*
H43B0.40640.23720.22890.087*
C440.39916 (18)0.2683 (12)0.1334 (3)0.0614 (16)
C450.3946 (2)0.1367 (12)0.0805 (3)0.0738 (19)
H450.3817−0.00060.08190.089*
C460.4086 (2)0.2006 (15)0.0252 (3)0.087 (2)
H460.40570.1063−0.00950.105*
C470.4267 (2)0.4038 (14)0.0225 (3)0.075 (2)
C480.4315 (2)0.5416 (13)0.0744 (3)0.081 (2)
H480.44400.68010.07320.097*
C490.4172 (2)0.4680 (13)0.1279 (3)0.075 (2)
H490.42010.56190.16270.090*
C500.4464 (3)0.326 (2)−0.0772 (4)0.193 (6)
H50A0.46710.2198−0.06200.289*
H50B0.45400.4015−0.11320.289*
H50C0.42100.2487−0.08880.289*
N10.15568 (14)0.5227 (11)0.2625 (2)0.0742 (16)
N20.34699 (14)0.2840 (9)0.20507 (19)0.0600 (13)
O10.12066 (13)0.1661 (8)0.30748 (19)0.0831 (14)
H10.12780.17050.27240.125*
O20.20340 (14)0.3502 (10)−0.0118 (2)0.0925 (15)
O30.33741 (13)0.6575 (7)0.26944 (19)0.0773 (13)
H3A0.34820.65530.23720.116*
O40.44186 (16)0.4827 (12)−0.0294 (2)0.1126 (19)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.062 (4)0.069 (5)0.048 (3)0.006 (4)0.001 (3)0.000 (4)
C20.128 (7)0.098 (6)0.069 (5)0.007 (5)0.002 (4)0.027 (5)
C30.164 (9)0.119 (9)0.081 (6)0.005 (8)0.014 (6)0.035 (6)
C40.133 (8)0.138 (9)0.068 (5)0.000 (7)0.023 (5)0.023 (7)
C50.143 (7)0.139 (9)0.063 (5)0.032 (7)0.032 (5)0.004 (6)
C60.153 (7)0.082 (5)0.065 (4)0.040 (6)0.047 (5)0.014 (4)
C70.076 (4)0.053 (4)0.063 (4)0.019 (4)0.015 (4)−0.007 (3)
C80.066 (4)0.080 (5)0.067 (4)0.009 (4)−0.003 (4)0.000 (4)
C90.065 (4)0.125 (8)0.072 (5)0.003 (5)−0.002 (4)0.011 (5)
C100.098 (6)0.070 (5)0.095 (5)−0.005 (5)−0.019 (5)−0.020 (5)
C110.088 (5)0.064 (5)0.074 (4)0.007 (4)0.005 (4)−0.008 (4)
C120.051 (3)0.051 (4)0.045 (3)−0.010 (3)0.009 (3)−0.005 (3)
C130.068 (4)0.069 (5)0.054 (4)0.005 (4)0.010 (3)−0.008 (3)
C140.060 (4)0.110 (6)0.050 (4)−0.009 (4)0.010 (3)−0.018 (4)
C170.062 (9)0.15 (2)0.083 (10)0.032 (10)0.009 (7)0.011 (11)
C160.058 (8)0.146 (18)0.061 (8)0.001 (10)−0.022 (6)−0.004 (9)
C150.054 (10)0.13 (2)0.041 (9)−0.009 (10)0.001 (7)−0.019 (12)
C15'0.09 (3)0.14 (4)0.11 (4)0.00 (2)−0.03 (2)−0.01 (3)
C16'0.09 (2)0.19 (5)0.12 (2)−0.02 (2)0.001 (16)0.01 (2)
C17'0.046 (14)0.14 (3)0.082 (17)0.044 (15)0.026 (11)−0.009 (18)
C180.081 (4)0.074 (5)0.067 (4)−0.001 (4)0.021 (4)0.005 (4)
C190.059 (4)0.069 (5)0.057 (4)0.002 (4)0.008 (3)−0.001 (4)
C200.076 (4)0.074 (5)0.071 (4)−0.010 (4)0.014 (4)−0.001 (4)
C210.077 (5)0.089 (6)0.069 (4)−0.006 (4)0.025 (4)0.014 (4)
C220.069 (4)0.092 (6)0.049 (4)0.008 (4)0.013 (3)0.002 (4)
C230.090 (5)0.066 (4)0.064 (4)−0.005 (4)0.017 (4)0.006 (4)
C240.079 (5)0.083 (6)0.057 (4)−0.009 (4)0.018 (3)0.012 (4)
C250.122 (7)0.120 (8)0.089 (5)0.013 (6)0.020 (5)−0.020 (6)
C260.076 (4)0.053 (4)0.058 (4)−0.004 (4)0.015 (3)−0.003 (4)
C270.115 (6)0.072 (6)0.114 (6)0.006 (5)0.049 (5)0.001 (5)
C280.157 (9)0.114 (8)0.139 (8)−0.020 (7)0.096 (7)−0.042 (7)
C290.118 (7)0.146 (10)0.098 (7)−0.047 (7)0.055 (5)−0.042 (8)
C300.158 (8)0.121 (8)0.070 (5)−0.024 (7)0.033 (5)0.002 (6)
C310.134 (6)0.092 (6)0.059 (4)0.001 (5)0.033 (4)0.005 (5)
C320.072 (4)0.048 (4)0.046 (3)0.000 (4)0.014 (3)−0.004 (3)
C330.072 (5)0.063 (5)0.068 (4)0.007 (4)0.004 (3)0.004 (4)
C340.077 (5)0.084 (6)0.058 (4)0.000 (4)0.009 (4)0.003 (4)
C350.075 (5)0.110 (7)0.073 (5)−0.011 (6)0.018 (4)−0.019 (5)
C360.085 (5)0.080 (6)0.078 (5)−0.017 (5)0.037 (4)−0.015 (5)
C370.101 (6)0.050 (4)0.051 (4)−0.006 (4)0.023 (3)−0.005 (3)
C380.081 (4)0.046 (4)0.051 (3)0.009 (3)0.018 (3)0.013 (3)
C390.065 (4)0.061 (4)0.051 (3)0.006 (3)0.003 (3)0.006 (3)
C400.074 (4)0.093 (6)0.058 (4)0.003 (4)0.002 (3)−0.003 (4)
C410.082 (5)0.213 (12)0.082 (5)−0.020 (7)0.011 (4)−0.027 (7)
C420.107 (6)0.097 (6)0.068 (4)−0.016 (5)−0.011 (4)0.007 (5)
C430.095 (5)0.078 (5)0.045 (3)0.029 (4)0.006 (3)0.009 (4)
C440.068 (4)0.062 (5)0.052 (4)0.014 (4)0.000 (3)−0.002 (4)
C450.102 (5)0.064 (4)0.058 (4)−0.005 (4)0.018 (4)−0.014 (4)
C460.108 (6)0.109 (7)0.046 (4)−0.015 (5)0.013 (4)−0.025 (4)
C470.078 (5)0.095 (6)0.051 (4)−0.015 (4)0.008 (4)0.003 (4)
C480.092 (5)0.076 (5)0.076 (5)−0.005 (4)0.017 (4)−0.012 (5)
C490.080 (5)0.080 (6)0.063 (4)0.009 (4)0.003 (4)−0.018 (4)
C500.250 (13)0.238 (15)0.107 (7)−0.108 (12)0.088 (8)−0.051 (9)
N10.055 (3)0.121 (5)0.045 (3)0.016 (3)0.002 (2)−0.005 (3)
N20.063 (3)0.069 (4)0.046 (3)0.005 (3)0.001 (2)0.002 (3)
O10.098 (3)0.072 (3)0.076 (3)0.037 (3)−0.001 (2)−0.019 (3)
O20.097 (3)0.114 (4)0.072 (3)−0.005 (3)0.028 (3)−0.009 (3)
O30.104 (3)0.056 (3)0.071 (3)0.017 (3)0.010 (2)0.019 (3)
O40.128 (4)0.146 (5)0.068 (3)−0.026 (4)0.028 (3)0.001 (4)

Geometric parameters (Å, °)

C1—C21.362 (10)C25—O21.421 (10)
C1—C61.376 (9)C25—H25A0.9600
C1—C131.540 (8)C25—H25B0.9600
C2—C31.388 (11)C25—H25C0.9600
C2—H20.9300C26—C271.350 (9)
C3—C41.308 (12)C26—C311.362 (9)
C3—H30.9300C26—C381.529 (8)
C4—C51.359 (13)C27—C281.394 (10)
C4—H40.9300C27—H270.9300
C5—C61.404 (9)C28—C291.291 (13)
C5—H50.9300C28—H280.9300
C6—H60.9300C29—C301.375 (14)
C7—C81.357 (8)C29—H290.9300
C7—C121.389 (8)C30—C311.403 (10)
C7—H70.9300C30—H300.9300
C8—C91.360 (10)C31—H310.9300
C8—H80.9300C32—C331.384 (8)
C9—C101.369 (11)C32—C371.411 (8)
C9—H90.9300C32—C381.530 (8)
C10—C111.379 (9)C33—C341.366 (8)
C10—H100.9300C33—H330.9300
C11—C121.383 (8)C34—C351.364 (11)
C11—H110.9300C34—H340.9300
C12—C131.525 (8)C35—C361.363 (10)
C13—O11.437 (8)C35—H350.9300
C13—C141.548 (9)C36—C371.394 (9)
C14—N11.482 (7)C36—H360.9300
C14—C151.55 (4)C37—H370.9300
C14—C15'1.59 (8)C38—O31.438 (7)
C14—H140.9800C38—C391.545 (9)
C17—N11.481 (8)C39—N21.493 (7)
C17—C161.542 (9)C39—C401.533 (8)
C17—H17A0.9700C39—H390.9800
C17—H17B0.9700C40—C411.499 (8)
C16—C151.531 (10)C40—H40A0.9700
C16—H16A0.9700C40—H40B0.9700
C16—H16B0.9700C41—C421.437 (9)
C15—H15A0.9700C41—H41A0.9700
C15—H15B0.9700C41—H41B0.9700
C15'—C16'1.535 (11)C42—N21.461 (8)
C15'—H15C0.9700C42—H42A0.9700
C15'—H15D0.9700C42—H42B0.9700
C16'—C17'1.528 (10)C43—N21.447 (7)
C16'—H16C0.9700C43—C441.507 (8)
C16'—H16D0.9700C43—H43A0.9700
C17'—N11.493 (10)C43—H43B0.9700
C17'—H17C0.9700C44—C491.349 (9)
C17'—H17D0.9700C44—C451.375 (8)
C18—N11.444 (7)C45—C461.384 (8)
C18—C191.496 (8)C45—H450.9300
C18—H18A0.9700C46—C471.362 (10)
C18—H18B0.9700C46—H460.9300
C19—C241.371 (9)C47—O41.367 (7)
C19—C201.392 (8)C47—C481.378 (9)
C20—C211.392 (8)C48—C491.374 (9)
C20—H200.9300C48—H480.9300
C21—C221.372 (9)C49—H490.9300
C21—H210.9300C50—O41.415 (12)
C22—C231.353 (9)C50—H50A0.9600
C22—O21.381 (7)C50—H50B0.9600
C23—C241.381 (8)C50—H50C0.9600
C23—H230.9300O1—H10.8200
C24—H240.9300O3—H3A0.8200
C2—C1—C6117.3 (6)H25A—C25—H25B109.5
C2—C1—C13121.3 (6)O2—C25—H25C109.5
C6—C1—C13121.4 (6)H25A—C25—H25C109.5
C1—C2—C3120.3 (9)H25B—C25—H25C109.5
C1—C2—H2119.9C27—C26—C31117.0 (6)
C3—C2—H2119.9C27—C26—C38121.7 (6)
C4—C3—C2123.1 (9)C31—C26—C38121.3 (6)
C4—C3—H3118.4C26—C27—C28122.0 (8)
C2—C3—H3118.4C26—C27—H27119.0
C3—C4—C5118.3 (8)C28—C27—H27119.0
C3—C4—H4120.9C29—C28—C27121.2 (9)
C5—C4—H4120.9C29—C28—H28119.4
C4—C5—C6120.5 (9)C27—C28—H28119.4
C4—C5—H5119.7C28—C29—C30119.3 (8)
C6—C5—H5119.7C28—C29—H29120.4
C1—C6—C5120.4 (8)C30—C29—H29120.4
C1—C6—H6119.8C29—C30—C31119.8 (9)
C5—C6—H6119.8C29—C30—H30120.1
C8—C7—C12122.0 (6)C31—C30—H30120.1
C8—C7—H7119.0C26—C31—C30120.6 (8)
C12—C7—H7119.0C26—C31—H31119.7
C7—C8—C9120.9 (7)C30—C31—H31119.7
C7—C8—H8119.5C33—C32—C37117.7 (6)
C9—C8—H8119.5C33—C32—C38122.9 (6)
C8—C9—C10118.8 (7)C37—C32—C38119.4 (6)
C8—C9—H9120.6C34—C33—C32121.6 (6)
C10—C9—H9120.6C34—C33—H33119.2
C9—C10—C11120.7 (7)C32—C33—H33119.2
C9—C10—H10119.7C35—C34—C33120.5 (7)
C11—C10—H10119.7C35—C34—H34119.8
C10—C11—C12121.1 (7)C33—C34—H34119.8
C10—C11—H11119.5C36—C35—C34120.2 (7)
C12—C11—H11119.5C36—C35—H35119.9
C11—C12—C7116.5 (5)C34—C35—H35119.9
C11—C12—C13120.2 (6)C35—C36—C37120.5 (7)
C7—C12—C13123.3 (5)C35—C36—H36119.7
O1—C13—C12110.1 (5)C37—C36—H36119.7
O1—C13—C1105.9 (5)C36—C37—C32119.6 (6)
C12—C13—C1110.4 (4)C36—C37—H37120.2
O1—C13—C14106.5 (5)C32—C37—H37120.2
C12—C13—C14112.3 (5)O3—C38—C26106.5 (5)
C1—C13—C14111.4 (5)O3—C38—C32110.6 (5)
N1—C14—C15103.1 (7)C26—C38—C32108.3 (5)
N1—C14—C13108.9 (5)O3—C38—C39106.2 (4)
C15—C14—C13109.8 (11)C26—C38—C39112.4 (5)
N1—C14—C15'110.1 (12)C32—C38—C39112.7 (5)
C15—C14—C15'18 (3)N2—C39—C40104.0 (4)
C13—C14—C15'121 (2)N2—C39—C38108.9 (5)
N1—C14—H14111.5C40—C39—C38114.2 (5)
C15—C14—H14111.5N2—C39—H39109.9
C13—C14—H14111.5C40—C39—H39109.9
C15'—C14—H1493.2C38—C39—H39109.9
N1—C17—C16104.0 (8)C41—C40—C39106.5 (5)
N1—C17—H17A110.9C41—C40—H40A110.4
C16—C17—H17A110.9C39—C40—H40A110.4
N1—C17—H17B110.9C41—C40—H40B110.4
C16—C17—H17B110.9C39—C40—H40B110.4
H17A—C17—H17B109.0H40A—C40—H40B108.6
C15—C16—C17102.5 (15)C42—C41—C40104.8 (6)
C15—C16—H16A111.3C42—C41—H41A110.8
C17—C16—H16A111.3C40—C41—H41A110.8
C15—C16—H16B111.3C42—C41—H41B110.8
C17—C16—H16B111.3C40—C41—H41B110.8
H16A—C16—H16B109.2H41A—C41—H41B108.9
C16—C15—C14107.7 (19)C41—C42—N2106.4 (6)
C16—C15—H15A110.2C41—C42—H42A110.5
C14—C15—H15A110.2N2—C42—H42A110.5
C16—C15—H15B110.2C41—C42—H42B110.5
C14—C15—H15B110.2N2—C42—H42B110.5
H15A—C15—H15B108.5H42A—C42—H42B108.6
C16'—C15'—C14103 (4)N2—C43—C44113.1 (5)
C16'—C15'—H15C111.2N2—C43—H43A109.0
C14—C15'—H15C111.2C44—C43—H43A109.0
C16'—C15'—H15D111.2N2—C43—H43B109.0
C14—C15'—H15D111.2C44—C43—H43B109.0
H15C—C15'—H15D109.1H43A—C43—H43B107.8
C17'—C16'—C15'105 (3)C49—C44—C45115.9 (6)
C17'—C16'—H16C110.7C49—C44—C43121.7 (6)
C15'—C16'—H16C110.7C45—C44—C43122.4 (7)
C17'—C16'—H16D110.7C44—C45—C46122.6 (7)
C15'—C16'—H16D110.7C44—C45—H45118.7
H16C—C16'—H16D108.8C46—C45—H45118.7
N1—C17'—C16'108.1 (18)C47—C46—C45118.9 (6)
N1—C17'—H17C110.1C47—C46—H46120.5
C16'—C17'—H17C110.1C45—C46—H46120.5
N1—C17'—H17D110.1C46—C47—O4123.8 (7)
C16'—C17'—H17D110.1C46—C47—C48120.3 (6)
H17C—C17'—H17D108.4O4—C47—C48115.9 (7)
N1—C18—C19112.9 (5)C49—C48—C47117.9 (7)
N1—C18—H18A109.0C49—C48—H48121.0
C19—C18—H18A109.0C47—C48—H48121.0
N1—C18—H18B109.0C44—C49—C48124.4 (6)
C19—C18—H18B109.0C44—C49—H49117.8
H18A—C18—H18B107.8C48—C49—H49117.8
C24—C19—C20116.1 (6)O4—C50—H50A109.5
C24—C19—C18121.6 (6)O4—C50—H50B109.5
C20—C19—C18122.2 (7)H50A—C50—H50B109.5
C19—C20—C21120.6 (7)O4—C50—H50C109.5
C19—C20—H20119.7H50A—C50—H50C109.5
C21—C20—H20119.7H50B—C50—H50C109.5
C22—C21—C20121.0 (6)C18—N1—C17119.8 (8)
C22—C21—H21119.5C18—N1—C14117.1 (5)
C20—C21—H21119.5C17—N1—C14112.0 (7)
C23—C22—C21119.1 (6)C18—N1—C17'100.4 (13)
C23—C22—O2126.0 (7)C17—N1—C17'34.3 (9)
C21—C22—O2115.0 (7)C14—N1—C17'103.2 (10)
C22—C23—C24119.7 (7)C43—N2—C42113.0 (5)
C22—C23—H23120.1C43—N2—C39114.8 (4)
C24—C23—H23120.1C42—N2—C39106.2 (5)
C19—C24—C23123.4 (6)C13—O1—H1109.5
C19—C24—H24118.3C22—O2—C25116.9 (6)
C23—C24—H24118.3C38—O3—H3A109.5
O2—C25—H25A109.5C47—O4—C50116.6 (8)
O2—C25—H25B109.5
C6—C1—C2—C3−0.3 (11)C33—C34—C35—C361.2 (10)
C13—C1—C2—C3179.1 (7)C34—C35—C36—C37−0.8 (10)
C1—C2—C3—C42.2 (15)C35—C36—C37—C320.4 (9)
C2—C3—C4—C5−2.9 (16)C33—C32—C37—C36−0.5 (8)
C3—C4—C5—C61.9 (15)C38—C32—C37—C36178.4 (5)
C2—C1—C6—C5−0.6 (11)C27—C26—C38—O3−18.6 (8)
C13—C1—C6—C5180.0 (7)C31—C26—C38—O3163.5 (6)
C4—C5—C6—C1−0.2 (14)C27—C26—C38—C32100.4 (7)
C12—C7—C8—C9−1.2 (10)C31—C26—C38—C32−77.5 (7)
C7—C8—C9—C100.7 (10)C27—C26—C38—C39−134.5 (7)
C8—C9—C10—C11−0.2 (11)C31—C26—C38—C3947.7 (8)
C9—C10—C11—C120.3 (11)C33—C32—C38—O3−172.7 (5)
C10—C11—C12—C7−0.8 (9)C37—C32—C38—O38.5 (7)
C10—C11—C12—C13−180.0 (6)C33—C32—C38—C2670.9 (7)
C8—C7—C12—C111.2 (8)C37—C32—C38—C26−107.9 (6)
C8—C7—C12—C13−179.6 (5)C33—C32—C38—C39−54.1 (7)
C11—C12—C13—O18.0 (7)C37—C32—C38—C39127.1 (5)
C7—C12—C13—O1−171.2 (5)O3—C38—C39—N246.9 (6)
C11—C12—C13—C1−108.6 (6)C26—C38—C39—N2162.9 (5)
C7—C12—C13—C172.3 (7)C32—C38—C39—N2−74.3 (5)
C11—C12—C13—C14126.5 (6)O3—C38—C39—C40−68.8 (6)
C7—C12—C13—C14−52.6 (7)C26—C38—C39—C4047.2 (6)
C2—C1—C13—O1−0.2 (8)C32—C38—C39—C40170.0 (5)
C6—C1—C13—O1179.2 (6)N2—C39—C40—C41−0.7 (8)
C2—C1—C13—C12118.9 (7)C38—C39—C40—C41117.9 (7)
C6—C1—C13—C12−61.7 (8)C39—C40—C41—C4221.2 (10)
C2—C1—C13—C14−115.7 (7)C40—C41—C42—N2−34.2 (10)
C6—C1—C13—C1463.7 (8)N2—C43—C44—C4981.8 (7)
O1—C13—C14—N146.6 (6)N2—C43—C44—C45−100.0 (7)
C12—C13—C14—N1−74.1 (6)C49—C44—C45—C461.7 (10)
C1—C13—C14—N1161.6 (5)C43—C44—C45—C46−176.6 (6)
O1—C13—C14—C15−65.7 (10)C44—C45—C46—C47−1.5 (11)
C12—C13—C14—C15173.7 (9)C45—C46—C47—O4179.4 (6)
C1—C13—C14—C1549.4 (10)C45—C46—C47—C480.9 (11)
O1—C13—C14—C15'−82 (2)C46—C47—C48—C49−0.6 (11)
C12—C13—C14—C15'157 (2)O4—C47—C48—C49−179.2 (6)
C1—C13—C14—C15'33 (2)C45—C44—C49—C48−1.3 (10)
N1—C17—C16—C15−31.8 (18)C43—C44—C49—C48177.0 (6)
C17—C16—C15—C1429.8 (18)C47—C48—C49—C440.8 (11)
N1—C14—C15—C16−16.0 (18)C19—C18—N1—C1751.2 (15)
C13—C14—C15—C1699.9 (16)C19—C18—N1—C14−167.6 (6)
C15'—C14—C15—C16−130 (7)C19—C18—N1—C17'81.6 (13)
N1—C14—C15'—C16'4(5)C16—C17—N1—C18166.6 (10)
C15—C14—C15'—C16'75 (5)C16—C17—N1—C1423.6 (17)
C13—C14—C15'—C16'132 (3)C16—C17—N1—C17'105 (3)
C14—C15'—C16'—C17'16 (5)C15—C14—N1—C18−149.1 (12)
C15'—C16'—C17'—N1−31 (4)C13—C14—N1—C1894.3 (7)
N1—C18—C19—C2469.7 (8)C15'—C14—N1—C18−131 (3)
N1—C18—C19—C20−108.7 (7)C15—C14—N1—C17−5.0 (17)
C24—C19—C20—C21−0.3 (9)C13—C14—N1—C17−121.6 (14)
C18—C19—C20—C21178.2 (6)C15'—C14—N1—C1713 (3)
C19—C20—C21—C222.6 (10)C15—C14—N1—C17'−39.9 (18)
C20—C21—C22—C23−2.4 (10)C13—C14—N1—C17'−156.5 (15)
C20—C21—C22—O2177.7 (6)C15'—C14—N1—C17'−22 (3)
C21—C22—C23—C240.0 (10)C16'—C17'—N1—C18154 (2)
O2—C22—C23—C24179.8 (6)C16'—C17'—N1—C17−77 (3)
C20—C19—C24—C23−2.2 (10)C16'—C17'—N1—C1432 (2)
C18—C19—C24—C23179.3 (6)C44—C43—N2—C4272.0 (7)
C22—C23—C24—C192.4 (10)C44—C43—N2—C39−166.0 (6)
C31—C26—C27—C280.8 (11)C41—C42—N2—C43161.0 (7)
C38—C26—C27—C28−177.2 (7)C41—C42—N2—C3934.4 (8)
C26—C27—C28—C29−3.8 (14)C40—C39—N2—C43−145.4 (6)
C27—C28—C29—C305.6 (15)C38—C39—N2—C4392.5 (6)
C28—C29—C30—C31−4.6 (15)C40—C39—N2—C42−19.8 (7)
C27—C26—C31—C300.2 (11)C38—C39—N2—C42−141.9 (6)
C38—C26—C31—C30178.1 (7)C23—C22—O2—C251.6 (9)
C29—C30—C31—C261.7 (13)C21—C22—O2—C25−178.6 (6)
C37—C32—C33—C341.0 (8)C46—C47—O4—C50−13.6 (11)
C38—C32—C33—C34−177.9 (6)C48—C47—O4—C50165.0 (8)
C32—C33—C34—C35−1.4 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.822.322.673 (8)106
O3—H3A···N20.822.332.672 (7)106

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2936).

References

  • Baker, K. V., Brown, M., Hughe, N., Skarnulis, A. J. & Sexton, A. (1991). J. Org. Chem.56, 698-703.
  • Bruker (2000). SADABS, SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Kagabu, S., Ishihara, R., Hieda, Y., Nishimura, K. & Naruse, Y. (2007). J. Agric. Food Chem.55, 812-818. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhao, S. K., Freeman, J. P., Bacon, C. L., Fox, G. B., O’Driscoll, E., Foley, A. G., Kelly, J., Regan, C., Mizsak, S. A. & Szmuszkovicz, J. (1999). Bioorg. Med. Chem.7, 1647-1654. [PubMed]

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