ortho-Perfluoroalkylation and Ethoxycarbonyldifluoromethylation of Aromatic Triazenes
Andreas Hafner; Angela Bihlmeier; Martin Nieger; Wim Klopper; Stefan Bräse; Journal of Organic Chemistry 78 (2013) 7938–7948; doi:10.1021/jo401145g

data_4028498
_publ_contact_author
;
        Martin Nieger
        Laboratory of Inorganic Chemistry
        Department of Chemistry
        Universitity of Helsinki
        P.O. Box 55
        FIN-00014 University of Helsinki
        Finland
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_publ_contact_author_email       martin.nieger@helsinki.fi
_publ_contact_author_fax         '++358 9 191 50198'
_publ_contact_author_phone       '++358 9 191 50192'
_publ_section_title
;
 ortho-Perfluoroalkylation and Ethoxycarbonyldifluoromethylation of
 Aromatic Triazenes
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7938
_journal_page_last               7948
_journal_paper_doi               10.1021/jo401145g
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C14 H16 F6 I N3'
_chemical_formula_sum            'C14 H16 F6 I N3'
_chemical_formula_weight         467.20
_chemical_name_systematic
; 
 (E)-1-(4-iodo-2,6-bis(trifluoromethyl)phenyl)-3,3-diisopropyl-
 triaz-1-ene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.26(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   13.155(2)
_cell_length_b                   14.570(2)
_cell_length_c                   27.548(4)
_cell_measurement_reflns_used    930
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.5
_cell_volume                     5280.0(13)
_computing_cell_refinement       EVALCCD
_computing_data_collection       Collect
_computing_data_reduction        EVALCCD
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 1 deg.'
_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  0.0599
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            67772
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    1.879
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.6814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plates
_exptl_crystal_F_000             2736
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.642
_refine_diff_density_min         -0.885
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     650
_refine_ls_number_reflns         12074
_refine_ls_number_restraints     1029
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0215P)^2^+10.6620P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0801
_reflns_number_gt                10144
_reflns_number_total             12074
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401145g_si_001_1.cif
_cod_data_source_block           sb446_tw_compound_9a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4028498