Synthesis of cationic π-extended imidazolium salts by sequential Cu-catalyzed arylation/annulation and photocyclization
Wang, Tianbao; Zheng, Qinze; Wang, Linhua; Huang, Zhenmei; Zhang, Huaxing; Zhang, Yuming; Zhang, Cheng; Gao, Ge; Chemical Communications  (2021) –; doi:10.1039/D1CC06194A

data_7129350
_publ_section_title
;
 Synthesis of cationic \p-extended imidazolium salts by sequential
 Cu-catalyzed arylation/annulation and photocyclization
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06194A
_journal_year                    2021
_chemical_formula_moiety         'B F4, C25 H15 N2'
_chemical_formula_sum            'C25 H15 B F4 N2'
_chemical_formula_weight         430.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-10-06 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.547(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4814(4)
_cell_length_b                   14.5840(9)
_cell_length_c                   16.2845(10)
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      23.898
_cell_measurement_theta_min      2.573
_cell_volume                     1958.23(19)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      301.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0999
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            90776
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_min         2.504
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1095 before and 0.0637 after correction.
The Ratio of minimum to maximum transmission is 0.9409.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4495
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0718
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1353P)^2^+0.6315P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2064
_refine_ls_wR_factor_ref         0.2533
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2523
_reflns_number_total             4495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06194a2.cif
_cod_data_source_block           mo_wtb_3_2_0m_a
_cod_database_code               7129350
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.959
_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), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23)
;
_shelx_res_checksum              96004
_olex2_submission_special_instructions 'No special instructions were received'