Deconstructing the Catalytic, Vicinal Difluorination of Alkenes: HF-Free Synthesis and Structural Study of p-TolIF2.
Sarie, Jérôme C; Thiehoff, Christian; Mudd, Richard J.; Daniliuc, Constantin G.; Kehr, Gerald; Gilmour, Ryan; The Journal of organic chemistry 82 (2017) 11792–11798; doi:10.1021/acs.joc.7b01671

data_4033310
_publ_section_title
;
 Deconstructing the Catalytic, Vicinal Difluorination of Alkenes: HF-Free
 Synthesis and Structural Study of p-TolIF2.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11792
_journal_page_last               11798
_journal_paper_doi               10.1021/acs.joc.7b01671
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C7 H7 F2 I'
_chemical_formula_weight         256.03
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.9542(8)
_cell_length_b                   11.5049(5)
_cell_length_c                   7.3428(3)
_cell_measurement_reflns_used    7847
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      27.4822
_cell_measurement_theta_min      2.2687
_cell_volume                     1516.74(11)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection
;

APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12280
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.88
_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    4.176
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.551
_refine_ls_abs_structure_details
;

Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.30(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3384
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0197
_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^)+(0.0132P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0386
_refine_ls_wR_factor_ref         0.0399
_reflns_number_gt                3134
_reflns_number_total             3384
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01671_si_001.cif
_cod_data_source_block           gil8757
_cod_database_code               4033310
_shelx_res_checksum              39713
_shelx_hkl_checksum              15887