Regio- and Stereoselective Carboindation of Internal Alkynyl Ethers with Organosilicon or -stannane Nucleophiles.
Kang, Kyoungmin; Nishimoto, Yoshihiro; Yasuda, Makoto; The Journal of organic chemistry 84 (2019) 13345–13363; doi:10.1021/acs.joc.9b01505

data_4034524
_publ_section_title
;
 Regio- and Stereoselective Carboindation of Internal Alkynyl Ethers with
 Organosilicon or -stannane Nucleophiles.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13345
_journal_page_last               13363
_journal_paper_doi               10.1021/acs.joc.9b01505
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C23 H21 Br4 I2 In N2 O3'
_chemical_formula_sum            'C23 H21 Br4 I2 In N2 O3'
_chemical_formula_weight         1061.68
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   19.2816(6)
_cell_length_b                   14.7591(4)
_cell_length_c                   20.9864(7)
_cell_measurement_reflns_used    11492
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.07
_cell_measurement_theta_min      2.10
_cell_volume                     5972.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.818
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            38695
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         30.90
_diffrn_reflns_theta_min         1.941
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.255
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            nONE
_exptl_crystal_density_diffrn    2.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       nONE
_exptl_crystal_F_000             3936.00
_refine_diff_density_max         2.230
_refine_diff_density_min         -1.660
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.663
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     337
_refine_ls_number_reflns         7726
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.026
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/\s^2^(Fo)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_ref         0.0332
_reflns_number_gt                6106
_reflns_number_total             7727
_reflns_threshold_expression     F>2.0\s(F)
_cod_data_source_file            jo9b01505_si_002.cif
_cod_data_source_block           4aa/3,5-Br2Py
_cod_database_code               4034524