Copper-catalyzed [2+3]-annulation of N-H imines with vinyl azides: access to polyaryl 2H-imidazoles.
Zhu, Zhongzhi; Lin, Hanze; Liang, Baihui; Huang, Junjie; Liang, Wanyi; Chen, Lu; Huang, Yubing; Chen, Xiuwen; Li, Yibiao; Chemical communications (Cambridge, England) 56 (2020) 5621–5624; doi:10.1039/c9cc10042c

data_7126351
_publ_section_title
;
 Copper-catalyzed [2+3]-annulation of N-H imines with vinyl azides: access
 to polyaryl 2H-imidazoles.
;
_journal_issue                   42
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5621
_journal_page_last               5624
_journal_paper_doi               10.1039/c9cc10042c
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C21 H14 Br2 N2'
_chemical_formula_sum            'C21 H14 Br2 N2'
_chemical_formula_weight         454.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-23
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-03 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.355(6)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   28.820(9)
_cell_length_b                   13.989(3)
_cell_length_c                   18.950(5)
_cell_measurement_reflns_used    6083
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.05
_cell_measurement_theta_min      2.21
_cell_volume                     7433(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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  0.0740
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            41109
_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         27.536
_diffrn_reflns_theta_min         1.452
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.367
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0895 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.7542.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_description       block
_exptl_crystal_F_000             3584
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         8464
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+10.5642P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.1121
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4498
_reflns_number_total             8464
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc10042c2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
         Adding full bibliography for 7126351.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C21 H14 Br2 N2)'
_cod_original_formula_sum        'C42 H28 Br4 N4'
_cod_original_formula_units_Z    8
_cod_original_formula_weight     908.32
_cod_database_code               7126351
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 Br4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(Br4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24),
  C26(H26), C27(H27), C29(H29), C32(H32), C33(H33), C35(H35), C36(H36),
 C38(H38), C39(H39), C41(H41), C42(H42)
;
_shelx_res_checksum              98926
_olex2_submission_special_instructions 'No special instructions were received'