Pd-Catalyzed multicomponent reaction of sulfonyl azides, primary amines and methyl α-isocyanoacetates: highly efficient synthesis of tetrasubstituted imidazolone derivatives
Wang, Fei; Xu, Pei; Liu, Bei-Bei; Wang, Shun-Yi; Ji, Shun-Jun; Organic Chemistry Frontiers 6 (2019) 3754–; doi:10.1039/C9QO01122F

data_1555195
_publ_section_title
;
 Pd-Catalyzed multicomponent reaction of sulfonyl azides, primary amines
 and methyl \a-isocyanoacetates: highly efficient synthesis of
 tetrasubstituted imidazolone derivatives
;
_journal_issue                   22
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3754
_journal_paper_doi               10.1039/C9QO01122F
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C31 H29 N3 O3 S'
_chemical_formula_sum            'C31 H29 N3 O3 S'
_chemical_formula_weight         523.63
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-21 deposited with the CCDC.	2019-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                102.001(2)
_cell_angle_beta                 100.8820(10)
_cell_angle_gamma                107.3370(10)
_cell_formula_units_Z            2
_cell_length_a                   9.8054(5)
_cell_length_b                   11.1916(5)
_cell_length_c                   13.8588(6)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.51
_cell_measurement_theta_min      2.26
_cell_volume                     1367.85(11)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            60843
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         2.259
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         6259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0647
_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^)+(0.0637P)^2^+1.1955P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1555
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4446
_reflns_number_total             6259
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo01122f2.cif
_cod_data_source_block           b180114c_0m
_cod_database_code               1555195
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.970
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C13(H13), C9(H9), C12(H12), C10(H10), C2(H2A), C21(H21), C24(H24),
 C17(H17), C6(H6), C20(H20), C3(H3), C19(H19), C25(H25), C5(H5), C18(H18),
 C27(H27), C28(H28), C26(H26)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              6859
_shelx_hkl_checksum              58784
_olex2_submission_special_instructions 'No special instructions were received'