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_7126637
_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 H15 F N2'
_chemical_formula_sum            'C21 H15 F N2'
_chemical_formula_weight         314.35
_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
_audit_block_doi                 10.5517/ccdc.csd.cc250jd4
_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
;
2020-04-13 deposited with the CCDC.	2020-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                89.574(9)
_cell_angle_beta                 84.573(9)
_cell_angle_gamma                78.861(9)
_cell_formula_units_Z            2
_cell_length_a                   8.768(7)
_cell_length_b                   9.173(7)
_cell_length_c                   10.452(8)
_cell_measurement_reflns_used    2032
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.49
_cell_measurement_theta_min      2.26
_cell_volume                     821.1(11)
_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)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.966
_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  0.0400
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9147
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.408
_diffrn_reflns_theta_min         1.957
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0693 before and 0.0475 after correction.
The Ratio of minimum to maximum transmission is 0.7375.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0696P)^2^+0.0074P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1401
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2216
_reflns_number_total             3614
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc10042c2.cif
_cod_data_source_block           1904232_0m
_cod_original_cell_volume        821.0(11)
_cod_database_code               7126637
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_shelx_res_checksum              2888
_olex2_submission_special_instructions 'No special instructions were received'