ReI-Catalyzed highly regio- and stereoselective C–H addition to terminal and internal alkynes
Chang, Yu-Che; Prakash, Sekar; Cheng, Chien-Hong; Organic Chemistry Frontiers 6 (2019) 432–; doi:10.1039/C8QO01068D

data_1554493
_publ_section_title
;
 ReI-Catalyzed highly regio- and stereoselective C--H addition to terminal
 and internal alkynes
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              432
_journal_paper_doi               10.1039/C8QO01068D
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C20 H14 N2'
_chemical_formula_weight         282.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2018-02-22 deposited with the CCDC.
2018-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                101.080(5)
_cell_angle_beta                 96.416(5)
_cell_angle_gamma                92.665(5)
_cell_formula_units_Z            2
_cell_length_a                   3.9188(4)
_cell_length_b                   12.5127(13)
_cell_length_c                   15.3057(15)
_cell_measurement_reflns_used    8090
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3494
_cell_measurement_theta_min      2.3526
_cell_volume                     730.13(13)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_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  0.0436
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25856
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.623
_diffrn_reflns_theta_min         1.366
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            'Light Brown'
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.010(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0677P)^2^+0.3791P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1325
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2581
_reflns_number_total             2993
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01068d2.cif
_cod_data_source_block           mo_180141LT_0m_a
_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 
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_cod_database_code               1554493
_shelxl_version_number           2014/6
_shelx_res_checksum              60856
_shelx_hkl_checksum              43881