Csp<sup>3</sup>-H bond functionalization of amines via tunable iminium ions: divergent synthesis of trifluoromethylated arylamines.
Shi, Lou; Wang, Mingshan; Pan, Ling; Li, Yifei; Liu, Qun; Chemical communications (Cambridge, England) 54 (2018) 8721–8724; doi:10.1039/c8cc04936j

data_7121955
_publ_section_title
;
 Csp<sup>3</sup>-H bond functionalization of amines via tunable iminium
 ions: divergent synthesis of trifluoromethylated arylamines.
;
_journal_issue                   63
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8721
_journal_page_last               8724
_journal_paper_doi               10.1039/c8cc04936j
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C22 H20 F6 N2'
_chemical_formula_sum            'C22 H20 F6 N2'
_chemical_formula_weight         426.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-12-04 deposited with the CCDC.
2018-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.355(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6136(7)
_cell_length_b                   15.5641(12)
_cell_length_c                   13.7093(11)
_cell_measurement_reflns_used    6318
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.13
_cell_measurement_theta_min      2.62
_cell_volume                     1987.2(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25644
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.721
_diffrn_reflns_theta_min         2.680
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   121.202
_exptl_transmission_factor_min   0.1374
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0525P)^2^+1.0272P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1460
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2478
_reflns_number_total             3781
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc04936j2.cif
_cod_data_source_block           2
_cod_depositor_comments          'Adding full bibliography for 7121955.cif.'
_cod_database_code               7121955
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(F1B)=Sof(F5A)=Sof(F3B)=Sof(F4A)=Sof(F2B)=Sof(F6A)=1-FVAR(1)
 Sof(F2A)=Sof(F3A)=Sof(F6B)=Sof(F4B)=Sof(F5B)=Sof(F1A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C5(H5), C17(H17), C21(H21)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C23(H23A,H23B), C25(H25A,H25B), C29(H29A,H29B), C30(H30A,H30B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14)
;
_shelx_res_checksum              40464
_olex2_submission_special_instructions 'No special instructions were received'