Asymmetric Dearomatization of Naphthols via a Rh-Catalyzed C(sp²)-H Functionalization/Annulation Reaction.
Zheng, Jun; Wang, Shao-Bo; Zheng, Chao; You, Shu-Li; Journal of the American Chemical Society 137 (2015) 4880–4883; doi:10.1021/jacs.5b01707

data_4129382
_publ_section_title
;
 Asymmetric Dearomatization of Naphthols via a Rh-Catalyzed
 C(sp&#x00B2;)-H Functionalization/Annulation Reaction.
;
_journal_issue                   15
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4880
_journal_page_last               4883
_journal_paper_doi               10.1021/jacs.5b01707
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H17 Br O'
_chemical_formula_weight         413.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 114.880(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7015(17)
_cell_length_b                   8.9613(10)
_cell_length_c                   15.8849(18)
_cell_measurement_reflns_used    4263
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      52.905
_cell_measurement_theta_min      4.958
_cell_volume                     1898.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11507
_diffrn_reflns_point_group_measured_fraction_full 0.895
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.479
_exptl_absorpt_coefficient_mu    2.177
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
; 
 Flack x determined using 1810 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.006(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         6635
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0493P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    0.777
_reflns_Friedel_fraction_max     0.765
_reflns_number_gt                5295
_reflns_number_total             6635
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b01707_si_002.cif
_cod_data_source_block           cd214620
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4129382
_shelxl_version_number           2013-4
_shelx_res_checksum              80280
_shelx_hkl_checksum              64202