Palladium-Catalyzed Intramolecular Aminotrifluoromethoxylation of Alkenes.
Chen, Chaohuang; Chen, Pinhong; Liu, Guosheng; Journal of the American Chemical Society 137 (2015) 15648–15651; doi:10.1021/jacs.5b10971

data_4129844
_publ_section_title
;
 Palladium-Catalyzed Intramolecular Aminotrifluoromethoxylation of
 Alkenes.
;
_journal_issue                   50
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15648
_journal_page_last               15651
_journal_paper_doi               10.1021/jacs.5b10971
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C19 H28 F3 N O3 S'
_chemical_formula_sum            'C19 H28 F3 N O3 S'
_chemical_formula_weight         407.48
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                86.431(8)
_cell_angle_beta                 89.627(8)
_cell_angle_gamma                71.394(7)
_cell_formula_units_Z            4
_cell_length_a                   8.376(4)
_cell_length_b                   12.224(6)
_cell_length_c                   21.474(10)
_cell_measurement_reflns_used    281
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      19.957
_cell_measurement_theta_min      3.441
_cell_volume                     2079.5(17)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.985
_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_unetI/netI     0.1555
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9460
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.653
_diffrn_reflns_theta_min         1.761
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2008/4 (Bruker,2010) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0695 before and 0.0347 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0781 before and 0.0430 after correction.
 The Ratio of minimum to maximum transmission is 0.67.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 18912 reflections, Rint = 0.0746
 (3928 with I > 3sig(I), Rint = 0.0457)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     496
_refine_ls_number_reflns         9460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.885
_refine_ls_R_factor_all          0.1490
_refine_ls_R_factor_gt           0.0605
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0387P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4577
_reflns_number_total             9460
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b10971_si_003.cif
_cod_data_source_block           mo_dm15698_0m
_cod_original_cell_volume        2079.5(16)
_cod_database_code               4129844
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.971
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7226(11) 0.2774(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C21(H21), C24(H24)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C20(H20A,
 H20B), C22(H22A,H22B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B)
3.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18), C33(H33), C34(H34), C36(H36), C37(H37)
3.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C19(H19A,H19B,
 H19C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C38(H38A,
 H38B,H38C)
;
_shelx_res_checksum              15650
_shelx_hkl_checksum              67078
_olex2_submission_special_instructions 'No special instructions were received'