Metal-Free Synthesis of Functionalized Tetrasubstituted Alkenes by Three-Component Reaction of Alkynes, Iodine, and Sodium Sulfinates.
Zhang, Jitan; Liang, Zhenda; Wang, Jun; Guo, Ziyi; Liu, Changqing; Xie, Meihua; ACS omega 3 (2018) 18002–18015; doi:10.1021/acsomega.8b02966

data_4516143
_publ_section_title
;
 Metal-Free Synthesis of Functionalized Tetrasubstituted Alkenes by
 Three-Component Reaction of Alkynes, Iodine, and Sodium Sulfinates.
;
_journal_issue                   12
_journal_name_full               'ACS omega'
_journal_page_first              18002
_journal_page_last               18015
_journal_paper_doi               10.1021/acsomega.8b02966
_journal_volume                  3
_journal_year                    2018
_chemical_formula_moiety         'C22 H13 F2 I O2 S'
_chemical_formula_sum            'C22 H13 F2 I O2 S'
_chemical_formula_weight         506.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.2560(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1270(17)
_cell_length_b                   9.2725(10)
_cell_length_c                   15.5544(17)
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.29
_cell_volume                     2059.7(4)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22436
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         1.629
_exptl_absorpt_coefficient_mu    1.688
_exptl_absorpt_correction_T_max  0.7398
_exptl_absorpt_correction_T_min  0.6975
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         1.118
_refine_diff_density_min         -1.020
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0098(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0295P)^2^+2.1917P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0795
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4272
_reflns_number_total             4692
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b02966_si_004.cif
_cod_data_source_block           test_0m
_cod_database_code               4516143
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.740
_shelx_estimated_absorpt_t_min   0.698
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13),
 C18(H18), C19(H19), C21(H21), C22(H22)
;
_shelx_res_checksum              27362
_shelx_hkl_checksum              19970
_olex2_submission_special_instructions 'No special instructions were received'