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_7240401
_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 H9 F I2 O'
_chemical_formula_sum            'C15 H9 F I2 O'
_chemical_formula_weight         478.02
_chemical_name_systematic
;
5-fluoro-1,2-diiodo-3-[(4-methoxyphenyl)ethynyl]benzene
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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.
;
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_cell_angle_gamma                90
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_cell_volume                     1459.34(5)
_computing_cell_refinement       'Bruker SAINT'
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_computing_publication_material  'Bruker SHELXTL'
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_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
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_diffrn_reflns_limit_l_min       -37
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
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_diffrn_reflns_theta_max         74.087
_diffrn_reflns_theta_min         2.889
_exptl_absorpt_coefficient_mu    33.866
_exptl_absorpt_correction_T_max  0.1121
_exptl_absorpt_correction_T_min  0.0046
_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
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_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexanes/dichloromethane'
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_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.037(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0150
_refine_ls_R_factor_gt           0.0149
_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^)+(0.0147P)^2^+0.2798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0379
_refine_ls_wR_factor_ref         0.0380
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_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2918
_reflns_number_total             2934
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           jus1809
_cod_depositor_comments
'Adding full bibliography for 7240398--7240401.cif.'
_cod_original_cell_volume        1459.35(5)
_cod_database_code               7240401
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.075
_shelx_estimated_absorpt_t_max   0.451
_shelx_res_checksum              20589