Iron(II)-Catalyzed Azidotrifluoromethylation of Olefins and N-Heterocycles for Expedient Vicinal Trifluoromethyl Amine Synthesis.
Zhu, Cheng-Liang; Wang, Cheng; Qin, Qi-Xue; Yruegas, Sam; Martin, Caleb D.; Xu, Hao; ACS catalysis 8 (2018) 5032–5037; doi:10.1021/acscatal.8b01253

data_4515658
_publ_section_title
;
 Iron(II)-Catalyzed Azidotrifluoromethylation of Olefins and
 N-Heterocycles for Expedient Vicinal Trifluoromethyl Amine Synthesis.
;
_journal_issue                   6
_journal_name_full               'ACS catalysis'
_journal_page_first              5032
_journal_page_last               5037
_journal_paper_doi               10.1021/acscatal.8b01253
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C15 H19 Fe N9 O2, C H2 Cl2'
_chemical_formula_sum            'C16 H21 Cl2 Fe N9 O2'
_chemical_formula_weight         498.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7551(17)
_cell_length_b                   18.856(2)
_cell_length_c                   8.4263(9)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.65
_cell_measurement_theta_min      2.65
_cell_volume                     2185.5(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1018
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            49112
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.870
_diffrn_reflns_theta_min         2.619
_exptl_absorpt_coefficient_mu    0.967
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.9178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABs
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_description       platelike
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details
;
 Flack x determined using 1598 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.029(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5180
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0664
_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^)+(0.0600P)^2^+6.4681P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1503
_refine_ls_wR_factor_ref         0.1609
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4103
_reflns_number_total             5180
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b01253_si_007.cif
_cod_data_source_block           XH01
_cod_database_code               4515658
_shelx_estimated_absorpt_t_min   0.454
_shelx_estimated_absorpt_t_max   0.855
_shelxl_version_number           2013-4
_shelx_res_checksum              30604
_shelx_hkl_checksum              92596