Rhodium-Catalyzed Cascade Oxidative Annulation Leading to Substituted Naphtho[1,8-bc]pyrans by Sequential Cleavage of C(sp2)-H/C(sp3)-H and C(sp2)-H/O-H Bonds
Xing Tan; Bingxian Liu; Xiangyu Li; Bin Li; Shansheng Xu; Haibin Song; Baiquan Wang; Journal of the American Chemical Society 134 (2012) 16163–16166; doi:10.1021/ja3075242

data_4118719
_publ_section_title
;
 Rhodium-Catalyzed Cascade Oxidative Annulation Leading to Substituted
 Naphtho[1,8-bc]pyrans by Sequential Cleavage of C(sp2)-H/C(sp3)-H and
 C(sp2)-H/O-H Bonds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16163
_journal_page_last               16166
_journal_paper_doi               10.1021/ja3075242
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C27 H19 N O'
_chemical_formula_weight         373.43
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 118.718(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.948(19)
_cell_length_b                   5.519(5)
_cell_length_c                   20.221(19)
_cell_measurement_reflns_used    3139
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      1.1
_cell_volume                     1952(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.22
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0910
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9418
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         1.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.9848
_exptl_absorpt_correction_type   MULTI=SCAN
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      0
_exptl_crystal_description       Prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.8(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4520
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0240P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0841
_reflns_number_gt                2781
_reflns_number_total             4520
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3075242_si_002_5.cif
_cod_data_source_block           3ae
_cod_database_code               4118719