Formation of Polycyclic Lactones through a Ruthenium-Catalyzed Ring-Closing Metathesis/Hetero-Pauson-Khand Reaction Sequence
David F. Finnegan; Marc L. Snapper; Journal of Organic Chemistry 76 (2011) 3644–3653; doi:10.1021/jo200359c

data_4026303
_publ_section_title
;
 Formation of Polycyclic Lactones through a Ruthenium-Catalyzed
 Ring-Closing Metathesis/Hetero-Pauson-Khand Reaction Sequence
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3644
_journal_page_last               3653
_journal_paper_doi               10.1021/jo200359c
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C19 H17 N O2'
_chemical_formula_weight         291.34
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_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 107.421(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5306(14)
_cell_length_b                   16.650(3)
_cell_length_c                   10.7514(17)
_cell_measurement_reflns_used    2634
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.45
_cell_volume                     1457.0(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_sigmaI/netI    0.0568
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
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_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10872
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9914
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1257
_reflns_number_gt                2676
_reflns_number_total             3625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200359c_si_004.cif
_cod_data_source_block           df01t
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