Synthesis of Novel Hexahydroindoles from the Dearomatization of Indoline
MacLeod, Brianna L.; Pienkos, Jared A.; Wilson, Katy B.; Sabat, Michal; Myers, William H.; Harman, W. Dean; Organometallics 35 (2016) 370–; doi:10.1021/acs.organomet.5b00959

data_4088250
_publ_section_title
;
 Synthesis of Novel Hexahydroindoles from the Dearomatization of Indoline
;
_journal_issue                   3
_journal_name_full               Organometallics
_journal_page_first              370
_journal_paper_doi               10.1021/acs.organomet.5b00959
_journal_volume                  35
_journal_year                    2016
_chemical_formula_sum            'C23 H36 B2 F5 N8 O2 P W'
_chemical_formula_weight         788.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 100.7520(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.6659(9)
_cell_length_b                   16.0480(9)
_cell_length_c                   25.4887(15)
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      36.91
_cell_measurement_theta_min      3.95
_cell_volume                     6295.5(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            41847
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.514
_exptl_absorpt_coefficient_mu    3.785
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_correction_T_min  0.6651
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3120
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.340
_refine_diff_density_max         1.491
_refine_diff_density_min         -2.391
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.232
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         6398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.232
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0159P)^2^+5.3119P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6249
_reflns_number_total             6398
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00959_si_002.cif
_cod_data_source_block           C23H36B2F5N8O2PW
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4088250
_shelx_estimated_absorpt_t_min   0.269
_shelx_estimated_absorpt_t_max   0.359
_shelxl_version_number           2013-4
_shelx_res_checksum              24233
_shelx_hkl_checksum              75107