Regio- and Stereoselective Synthesis of Thiazole-Containing Triarylethylenes by Hydroarylation of Alkynes.
Lee, Woohyeong; Shin, Changhoon; Park, Soo Eun; Joo, Jung Min; The Journal of organic chemistry 84 (2019) 12913–12924; doi:10.1021/acs.joc.9b01619

data_4034087
_publ_section_title
;
 Regio- and Stereoselective Synthesis of Thiazole-Containing
 Triarylethylenes by Hydroarylation of Alkynes.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12913
_journal_page_last               12924
_journal_paper_doi               10.1021/acs.joc.9b01619
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C17 H13 N S'
_chemical_formula_weight         263.34
_space_group_crystal_system      trigonal
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_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
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_cell_angle_beta                 90
_cell_angle_gamma                120
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_cell_length_b                   9.7128(17)
_cell_length_c                   12.1114(18)
_cell_measurement_reflns_used    8356
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.42
_cell_volume                     989.5(3)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Breeze CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12439
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.490
_diffrn_reflns_theta_min         2.421
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0291
_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^)+(0.0364P)^2^+0.1476P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0727
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3076
_reflns_number_total             3233
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01619_si_002.cif
_cod_data_source_block           ss
_cod_original_cell_volume        989.5(4)
_cod_database_code               4034087
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.960
_shelx_res_checksum              97982
_shelx_hkl_checksum              52450