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_7240399
_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         'C15 H7 F3 I2'
_chemical_formula_sum            'C15 H7 F3 I2'
_chemical_formula_weight         498.01
_chemical_name_systematic
;
1,2-diiodo-3-{[4-(trifluoromethyl)phenyl]ethynyl}benzene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 90.1567(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1687(8)
_cell_length_b                   4.3193(3)
_cell_length_c                   27.7962(17)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.22
_cell_volume                     1460.97(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0171
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            16567
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.530
_diffrn_reflns_theta_min         1.465
_exptl_absorpt_coefficient_mu    4.324
_exptl_absorpt_correction_T_max  0.3623
_exptl_absorpt_correction_T_min  0.2634
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.264
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexanes/dichloromethane'
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.119
_refine_diff_density_max         1.059
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0241P)^2^+1.1974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0563
_refine_ls_wR_factor_ref         0.0575
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4127
_reflns_number_total             4473
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra01569e2.cif
_cod_data_source_block           jus1808
_cod_depositor_comments
'Adding full bibliography for 7240398--7240401.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240399
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.502
_shelx_estimated_absorpt_t_max   0.627
_shelx_res_checksum              89203