Construction of Vicinal All-Carbon Quaternary Stereocenters Enabled by a Catalytic Asymmetric Dearomatization Reaction of β-Naphthols with 3-Bromooxindoles
Liu, Xihong; Wang, Pengxin; Bai, Lutao; Li, Dan; Wang, Linqing; Yang, Dongxu; Wang, Rui; ACS Catalysis 8 (2018) 10888–; doi:10.1021/acscatal.8b03905

data_4515755
_publ_section_title
;
 Construction of Vicinal All-Carbon Quaternary Stereocenters Enabled by a
 Catalytic Asymmetric Dearomatization Reaction of \b-Naphthols with
 3-Bromooxindoles
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              10888
_journal_paper_doi               10.1021/acscatal.8b03905
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_sum            'C25 H21 N O2 S'
_chemical_formula_weight         399.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 107.363(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.960(10)
_cell_length_b                   8.264(3)
_cell_length_c                   9.337(4)
_cell_measurement_reflns_used    3445
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.42
_cell_measurement_theta_min      2.36
_cell_volume                     1985.5(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4763
_diffrn_reflns_point_group_measured_fraction_full 0.874
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         1.583
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.964
_exptl_transmission_factor_min   0.957
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1102 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3065
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0780P)^2^+0.0078P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1048
_reflns_Friedel_coverage         0.667
_reflns_Friedel_fraction_full    0.757
_reflns_Friedel_fraction_max     0.757
_reflns_number_gt                2892
_reflns_number_total             3065
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b03905_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1985.4(13)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4515755
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.964
_shelx_res_checksum              36746
_shelx_hkl_checksum              43530