KO(t)Bu-Initiated Aryl C-H Iodination: A Powerful Tool for the Synthesis of High Electron Affinity Compounds.
Shi, Qinqin; Zhang, Siyuan; Zhang, Junxiang; Oswald, Victoria F.; Amassian, Aram; Marder, Seth R.; Blakey, Simon B.; Journal of the American Chemical Society 138 (2016) 3946–3949; doi:10.1021/jacs.5b12259

data_4129973
_publ_section_title
;
 KO(t)Bu-Initiated Aryl C-H Iodination: A Powerful Tool for the Synthesis
 of High Electron Affinity Compounds.
;
_journal_issue                   12
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3946
_journal_page_last               3949
_journal_paper_doi               10.1021/jacs.5b12259
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C6 H2 F I N2 S'
_chemical_formula_sum            'C6 H2 F I N2 S'
_chemical_formula_weight         280.06
_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
_audit_creation_date             2015-06-16
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2015.06.08 svn.r3188 for OlexSys, GUI svn.r5047)
;
_cell_angle_alpha                70.391(2)
_cell_angle_beta                 67.906(2)
_cell_angle_gamma                65.029(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1942(17)
_cell_length_b                   7.6321(18)
_cell_length_c                   8.348(2)
_cell_measurement_reflns_used    5885
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.721
_cell_measurement_theta_min      2.693
_cell_volume                     376.38(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'Superflip (L. Palatinus & G. Chapuis, 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6561
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.734
_diffrn_reflns_theta_min         3.012
_diffrn_source                   'sealed tube'
_diffrn_source_current           35
_diffrn_source_voltage           45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.476
_exptl_absorpt_correction_T_max  0.7504
_exptl_absorpt_correction_T_min  0.0898
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1426 before and 0.0579 after correction.
The Ratio of minimum to maximum transmission is 0.1197.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.471
_exptl_crystal_description       plate
_exptl_crystal_F_000             260
_exptl_crystal_recrystallization_method
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.449
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.072
_refine_diff_density_max         2.350
_refine_diff_density_min         -1.033
_refine_diff_density_rms         0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         2314
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0291
_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^)+(0.0393P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0742
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2148
_reflns_number_total             2314
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b12259_si_002.cif
_cod_data_source_block           qs-ii-267-5
_cod_original_cell_volume        376.37(15)
_cod_database_code               4129973
_shelx_estimated_absorpt_t_max   0.739
_shelx_estimated_absorpt_t_min   0.238
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 C2, N2, C3, C1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N2, S1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N2, C2, C1, N1, S1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3)
;
_shelx_res_checksum              7655
_shelx_hkl_checksum              39054
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id QS-11-267-5
_olex2_submission_special_instructions 'No special instructions were received'