Selective oxymetalation of terminal alkynes <i>via</i> 6-<i>endo</i> cyclization: mechanistic investigation and application to the efficient synthesis of 4-substituted isocoumarins.
Kita, Yuji; Yata, Tetsuji; Nishimoto, Yoshihiro; Chiba, Kouji; Yasuda, Makoto; Chemical science 9 (2018) 6041–6052; doi:10.1039/c8sc01537f

data_1549558
_publ_section_title
;
 Selective oxymetalation of terminal alkynes <i>via</i> 6-<i>endo</i>
 cyclization: mechanistic investigation and application to the efficient
 synthesis of 4-substituted isocoumarins.
;
_journal_issue                   28
_journal_name_full               'Chemical science'
_journal_page_first              6041
_journal_page_last               6052
_journal_paper_doi               10.1039/c8sc01537f
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C17 H20 I2 In N O6'
_chemical_formula_sum            'C17 H20 I2 In N O6'
_chemical_formula_weight         702.98
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_update_record
;
2017-09-25 deposited with the CCDC.
2018-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                94.244(2)
_cell_angle_beta                 92.845(2)
_cell_angle_gamma                113.4183(19)
_cell_formula_units_Z            2
_cell_length_a                   8.5335(6)
_cell_length_b                   8.9158(6)
_cell_length_c                   15.6189(10)
_cell_measurement_reflns_used    13083
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      3.02
_cell_volume                     1083.39(13)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_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 10.000
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
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_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9798
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
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_exptl_absorpt_coefficient_mu    3.971
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_exptl_absorpt_correction_type   multi-scan
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_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
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_exptl_crystal_size_max          0.500
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0010Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                4667
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_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c8sc01537f2.cif
_cod_data_source_block           1823______________________
_cod_depositor_comments
'Adding full bibliography for 1549558--1549561.cif.'
_cod_database_code               1549558