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_1549559
_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         'C10 H8 I3 In O2'
_chemical_formula_sum            'C10 H8 I3 In O2'
_chemical_formula_weight         655.71
_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
;
2017-10-13 deposited with the CCDC.
2018-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                71.041(7)
_cell_angle_beta                 73.634(6)
_cell_angle_gamma                78.807(6)
_cell_formula_units_Z            2
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_cell_length_b                   10.6797(9)
_cell_length_c                   10.9105(8)
_cell_measurement_reflns_used    5776
_cell_measurement_temperature    123
_cell_measurement_theta_max      74.07
_cell_measurement_theta_min      4.39
_cell_volume                     766.42(10)
_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'
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_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
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_diffrn_reflns_limit_k_min       -13
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_diffrn_reflns_limit_l_min       -9
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_exptl_absorpt_correction_T_min  0.001
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_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            metalliccolourless
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_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
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'Larson (1970) Crystallographic Computing eq. 22'
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_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
    Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
    9471.2800    13325.8000    4355.8900
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0805
_reflns_number_gt                2743
_reflns_number_total             3090
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_cod_data_source_block           xcalibur
_cod_depositor_comments
'Adding full bibliography for 1549558--1549561.cif.'
_cod_database_code               1549559