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_4118717
_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            'C38 H25 N O2'
_chemical_formula_weight         527.60
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.81(3)
_cell_angle_beta                 96.14(3)
_cell_angle_gamma                104.89(3)
_cell_formula_units_Z            2
_cell_length_a                   11.087(2)
_cell_length_b                   11.313(2)
_cell_length_c                   11.699(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1400.5(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1265
_diffrn_reflns_av_sigmaI/netI    0.2045
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11852
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.9848
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         4918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.1826
_refine_ls_R_factor_gt           0.0690
_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^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1830
_reflns_number_gt                1454
_reflns_number_total             4918
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3075242_si_002_3.cif
_cod_data_source_block           3la-2
_cod_database_code               4118717