A rhodium-catalyzed three-component reaction of arylisocyanides, trifluorodiazoethane, and activated methylene isocyanides or azomethine ylides: an efficient synthesis of trifluoroethyl-substituted imidazoles
Yu, Yang; Zhang, Yan; Wang, Zhuo; Liang, Yong-Xin; Zhao, Yu-Long; Organic Chemistry Frontiers 6 (2019) 3657–; doi:10.1039/C9QO00856J

data_1555088
_publ_section_title
;
 A rhodium-catalyzed three-component reaction of arylisocyanides,
 trifluorodiazoethane, and activated methylene isocyanides or azomethine
 ylides: an efficient synthesis of trifluoroethyl-substituted imidazoles
;
_journal_issue                   21
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3657
_journal_paper_doi               10.1039/C9QO00856J
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C26 H20 Cl F3 N2 O2'
_chemical_formula_weight         484.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-09-07 deposited with the CCDC.	2019-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.172(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2179(10)
_cell_length_b                   17.509(2)
_cell_length_c                   18.867(3)
_cell_measurement_reflns_used    4608
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.39
_cell_measurement_theta_min      4.76
_cell_volume                     2346.9(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6736
_diffrn_reflns_point_group_measured_fraction_full 0.760
_diffrn_reflns_point_group_measured_fraction_max 0.760
_diffrn_reflns_theta_full        67.089
_diffrn_reflns_theta_max         67.089
_diffrn_reflns_theta_min         4.762
_exptl_absorpt_coefficient_mu    1.881
_exptl_absorpt_correction_T_max  0.844
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 826 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(13)
_refine_ls_extinction_coef       0.00140(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0288P)^2^+1.4604P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.558
_reflns_Friedel_fraction_full    0.546
_reflns_Friedel_fraction_max     0.546
_reflns_number_gt                2677
_reflns_number_total             3193
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00856j2.cif
_cod_data_source_block           zhaoyl190513_1_0m
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1555088
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              78341
_shelx_hkl_checksum              70214