Synthesis of Five-Membered Iodine-Nitrogen Heterocycles from Benzimidazole-Based Iodonium Salts.
Vlasenko, Yulia A.; Postnikov, Pavel S.; Trusova, Marina E.; Shafir, Alexandr; Zhdankin, Viktor V.; Yoshimura, Akira; Yusubov, Mekhman S.; The Journal of organic chemistry 83 (2018) 12056–12070; doi:10.1021/acs.joc.8b01995

data_4035252
_publ_section_title
;
 Synthesis of Five-Membered Iodine-Nitrogen Heterocycles from
 Benzimidazole-Based Iodonium Salts.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12056
_journal_page_last               12070
_journal_paper_doi               10.1021/acs.joc.8b01995
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C23 H19 Cl F3 I N2 O3 S'
_chemical_formula_weight         622.81
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                71.101(3)
_cell_angle_beta                 80.004(3)
_cell_angle_gamma                77.429(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0971(16)
_cell_length_b                   11.752(2)
_cell_length_c                   13.384(3)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.59
_cell_volume                     1168.7(4)
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
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_diffrn_reflns_point_group_measured_fraction_full 0.997
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.430
_diffrn_reflns_theta_min         1.860
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_current           0.6
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    1.627
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 TWINABS Version 2008/0 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.770
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_refine_diff_density_max         2.789
_refine_diff_density_min         -1.373
_refine_diff_density_rms         0.169
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_parameters     529
_refine_ls_number_reflns         6389
_refine_ls_number_restraints     473
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0614
_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^)+(0.0886P)^2^+1.9044P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1568
_refine_ls_wR_factor_ref         0.1700
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5049
_reflns_number_total             6389
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01995_si_005.cif
_cod_data_source_block           mo_YV163-05
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1168.6(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4035252
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.854
_shelx_estimated_absorpt_t_max   0.953
_shelx_res_checksum              86473
_shelx_hkl_checksum              57514