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_7129349
_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         'C F3 O3 S, C33 H19 N2'
_chemical_formula_sum            'C34 H19 F3 N2 O3 S'
_chemical_formula_weight         592.57
_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             2021-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-10-06 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                81.633(5)
_cell_angle_beta                 87.519(5)
_cell_angle_gamma                83.289(5)
_cell_formula_units_Z            2
_cell_length_a                   9.3567(6)
_cell_length_b                   10.7079(6)
_cell_length_c                   14.3234(8)
_cell_measurement_reflns_used    2594
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3180
_cell_measurement_theta_min      3.2420
_cell_volume                     1409.56(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -83.00    1.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -57.0000   30.0000 84

  2 omega  -23.00    5.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -99.0000    0.0000 28

  3 omega  -21.00   21.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -99.0000 -180.0000 42

  4 omega  -21.00   35.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6648  -99.0000 -180.0000 56

  5 omega   -1.00   87.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6648   38.0000    0.0000 88

  6 omega  -54.00   37.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6648  -19.0000 -180.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0755172000
_diffrn_orient_matrix_UB_12      0.0016017000
_diffrn_orient_matrix_UB_13      -0.0039471000
_diffrn_orient_matrix_UB_21      0.0053110000
_diffrn_orient_matrix_UB_22      -0.0665929000
_diffrn_orient_matrix_UB_23      0.0143416000
_diffrn_orient_matrix_UB_31      -0.0099667000
_diffrn_orient_matrix_UB_32      0.0101198000
_diffrn_orient_matrix_UB_33      0.0478104000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11362
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.952
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.992
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0749
_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^)+(0.1137P)^2^+0.2339P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2067
_refine_ls_wR_factor_ref         0.2298
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3522
_reflns_number_total             5757
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06194a2.cif
_cod_data_source_block           210907_s2_wtb
_cod_original_cell_volume        1409.56(14)
_cod_database_code               7129349
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         c12h12n2o3s1
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.942
_reflns_odcompleteness_completeness 99.84
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28), C29(H29),
  C30(H30), C31(H31)
;
_shelx_res_checksum              54222
_olex2_submission_special_instructions 'No special instructions were received'