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_4026301
_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_moiety         'C15 H17 N O2'
_chemical_formula_sum            'C15 H17 N O2'
_chemical_formula_weight         243.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.370(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.509(2)
_cell_length_b                   5.4181(11)
_cell_length_c                   19.681(4)
_cell_measurement_reflns_used    2943
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.53
_cell_volume                     1210.9(4)
_computing_cell_refinement       'SMART, SAINT'
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXP-93 (Sheldrick, 1993)'
_computing_publication_material  'SHELXCIF-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '0.3 deg wide \w exposures'
_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  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12019
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_correction_T_min  0.9930
_exptl_absorpt_correction_type   'multi-scan (SADABS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       na
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2384
_refine_ls_number_restraints     179
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0477P)^2^+0.9529P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1378
_reflns_number_gt                1804
_reflns_number_total             2384
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200359c_si_002.cif
_cod_data_source_block           C15H17NO2
_cod_database_code               4026301