Halogen-Bond-Promoted Double Radical Isocyanide Insertion under Visible-Light Irradiation: Synthesis of 2-Fluoroalkylated Quinoxalines.
Sun, Xiaoyang; Wang, Wenmin; Li, Yanle; Ma, Jing; Yu, Shouyun; Organic letters 18 (2016) 4638–4641; doi:10.1021/acs.orglett.6b02271

data_1555736
_publ_section_title
;
 Halogen-Bond-Promoted Double Radical Isocyanide Insertion under
 Visible-Light Irradiation: Synthesis of 2-Fluoroalkylated Quinoxalines.
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_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4638
_journal_page_last               4641
_journal_paper_doi               10.1021/acs.orglett.6b02271
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C51 H18 F51 I3 N6 O3'
_chemical_formula_weight         2112.41
_chemical_melting_point          ?
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.096(2)
_cell_angle_beta                 85.285(2)
_cell_angle_gamma                73.926(2)
_cell_formula_units_Z            2
_cell_length_a                   11.5390(13)
_cell_length_b                   16.419(2)
_cell_length_c                   18.984(2)
_cell_measurement_reflns_used    5923
_cell_measurement_temperature    300
_cell_measurement_theta_max      24.1602
_cell_measurement_theta_min      2.2017
_cell_volume                     3368.0(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22685
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.581
_exptl_absorpt_correction_T_max  0.8839
_exptl_absorpt_correction_T_min  0.7427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS:Bruker, 2000'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.083
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.325
_refine_diff_density_min         -1.296
_refine_diff_density_rms         0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1202
_refine_ls_number_reflns         15275
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1135P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1700
_refine_ls_wR_factor_ref         0.2052
_reflns_number_gt                8221
_reflns_number_total             15275
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02271_si_003.cif
_cod_data_source_block           3-iodo-5-methoxy-2-(perfluorooctyl)quinoxaline
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

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

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               1555736