Three-Component Cascade Synthesis of Fully-substituted Trifluoromethyl Pyrroles via a Cu(II)/Rh(Ⅲ)-promoted aza-Michael Addition/Trifluoromethylation Cyclization/Oxidation Reaction.
Ge, Junying; Ding, Qiuping; Wang, Xinhua; Peng, Yiyuan; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03470

data_4038456
_publ_section_title
;
 Three-Component Cascade Synthesis of Fully-substituted Trifluoromethyl
 Pyrroles via a Cu(II)/Rh(&#x2162;)-promoted aza-Michael
 Addition/Trifluoromethylation Cyclization/Oxidation Reaction.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03470
_journal_year                    2020
_chemical_formula_moiety         'C24 H14 F6 N2 O3'
_chemical_formula_sum            'C24 H14 F6 N2 O3'
_chemical_formula_weight         492.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.6397(7)
_cell_length_b                   11.6276(6)
_cell_length_c                   20.5913(9)
_cell_measurement_reflns_used    6864
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9750
_cell_measurement_theta_min      3.7980
_cell_volume                     4462.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -83.00   1.00   1.00   20.40    --  -15.76 -57.00 -60.00   84
  2  \w    -85.00  54.00   1.00   20.40    --  -15.76   0.00   0.00  139
  3  \w    -32.00  15.00   1.00   20.40    --  -15.76  57.00  90.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0168808000
_diffrn_orient_matrix_UB_12      0.0251126000
_diffrn_orient_matrix_UB_13      0.0274393000
_diffrn_orient_matrix_UB_21      -0.0116723000
_diffrn_orient_matrix_UB_22      -0.0466337000
_diffrn_orient_matrix_UB_23      0.0194814000
_diffrn_orient_matrix_UB_31      0.0320734000
_diffrn_orient_matrix_UB_32      -0.0301998000
_diffrn_orient_matrix_UB_33      -0.0073344000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            25753
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.283
_diffrn_reflns_theta_min         3.430
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.37b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.143
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.466
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5511
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.466
_refine_ls_R_factor_all          0.1469
_refine_ls_R_factor_gt           0.1083
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3634
_refine_ls_wR_factor_ref         0.3985
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3476
_reflns_number_total             5511
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03470_si_002.cif
_cod_data_source_block           gjy20181101
_cod_database_code               4038456
_shelxl_version_number           2014-1
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.987
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C17(H17), C23(H23), C20(H20), C13(H13), C15(H15), C16(H16),
 C22(H22), C14(H14), C10(H10), C6(H6), C8(H8), C9(H9), C7(H7)
;
_shelx_res_checksum              49706
_shelx_hkl_checksum              31807
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.671
_oxdiff_exptl_absorpt_empirical_full_min 0.672