Palladium-catalyzed highly regioselective mono and double Sonogashira cross-coupling reactions of 5-substituted-1,2,3-triiodobenzene under ambient conditions
Al-Zoubi, Raed M.; Al-Omari, Mothana K.; Al-Jammal, Walid K.; Ferguson, Michael J.; RSC Advances 10 (2020) 16366–16376; doi:10.1039/D0RA01569E

data_7240398
_publ_section_title
;
 Palladium-catalyzed highly regioselective mono and double Sonogashira
 cross-coupling reactions of 5-substituted-1,2,3-triiodobenzene under
 ambient conditions
;
_journal_issue                   28
_journal_name_full               'RSC Advances'
_journal_page_first              16366
_journal_page_last               16376
_journal_paper_doi               10.1039/D0RA01569E
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C24 H10 Cl F6 I'
_chemical_formula_sum            'C24 H10 Cl F6 I'
_chemical_formula_weight         574.67
_chemical_name_systematic
;
5-chloro-2-iodo-1,3-bis{[4-trifluoromethyl)phenyl]ethynyl}benzene
;
_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
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-02-05 deposited with the CCDC.	2020-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                91.3034(15)
_cell_angle_beta                 91.6389(14)
_cell_angle_gamma                111.5614(14)
_cell_formula_units_Z            2
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_cell_length_b                   10.0715(12)
_cell_length_c                   11.7314(14)
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_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.24
_cell_volume                     1075.9(2)
_computing_cell_refinement       'Bruker SAINT'
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_computing_molecular_graphics    'Bruker SHELXTL'
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_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick 2015)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8291
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.590
_diffrn_reflns_theta_min         1.738
_exptl_absorpt_coefficient_mu    1.673
_exptl_absorpt_correction_T_max  0.9260
_exptl_absorpt_correction_T_min  0.7647
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_description       fragment
_exptl_crystal_F_000             556
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.103
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0510P)^2^+0.8785P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3710
_reflns_number_total             4456
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra01569e2.cif
_cod_data_source_block           jus1803
_cod_depositor_comments
'Adding full bibliography for 7240398--7240401.cif.'
_cod_database_code               7240398
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.689
_shelx_estimated_absorpt_t_max   0.847
_shelx_res_checksum              8656