Preparation of Polysubstituted Isochromanes by Addition of ortho-Lithiated Aryloxiranes to Enaminones
Antonio Salomone; Filippo Maria Perna; Francesca Claudia Sassone; Aurelia Falcicchio; Jure Bezenšek; Jurij Svete; Branko Stanovnik; Saverio Florio; Vito Capriati; Journal of Organic Chemistry 78 (2013) 11059–11065; doi:10.1021/jo401689e

data_4028699
_publ_section_title
;
 Preparation of Polysubstituted Isochromanes by Addition of
 ortho-Lithiated Aryloxiranes to Enaminones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11059
_journal_page_last               11065
_journal_paper_doi               10.1021/jo401689e
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C27 H29 N O4'
_chemical_formula_weight         431.51
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 105.71
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.212
_cell_length_b                   13.035
_cell_length_c                   8.790
_cell_measurement_temperature    293(2)
_cell_volume                     2339.632
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1470
_diffrn_reflns_av_sigmaI/netI    0.1583
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13659
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         5.07
_exptl_absorpt_coefficient_mu    0.082
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             920
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   7(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5133
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1773
_refine_ls_R_factor_gt           0.0768
_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^)+(0.0653P)^2^+0.1294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1435
_refine_ls_wR_factor_ref         0.1827
_reflns_number_gt                2494
_reflns_number_total             5133
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401689e_si_002.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        2339.7
_cod_database_code               4028699