Transition-Metal-Free Dehydrosilylative Difluoroamidation of Tetrahydroisoquinolines under Mild Conditions.
Chen, Qiao; Zhou, Jiawei; Wang, Yanan; Wang, Chao; Liu, Xihong; Xu, Zhaoqing; Lin, Li; Wang, Rui; Organic letters 17 (2015) 4212–4215; doi:10.1021/acs.orglett.5b01997

data_1529420
_publ_section_title
;
 Transition-Metal-Free Dehydrosilylative Difluoroamidation of
 Tetrahydroisoquinolines under Mild Conditions.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4212
_journal_page_last               4215
_journal_paper_doi               10.1021/acs.orglett.5b01997
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H23 Cl F2 N2 O'
_chemical_formula_sum            'C21 H23 Cl F2 N2 O'
_chemical_formula_weight         392.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-21
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.299(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1195(9)
_cell_length_b                   25.1207(17)
_cell_length_c                   6.0786(4)
_cell_measurement_reflns_used    1124
_cell_measurement_temperature    173
_cell_measurement_theta_max      23.2020
_cell_measurement_theta_min      4.1820
_cell_volume                     1949.6(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N2
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -15.00   24.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000   30.0000 26

  2 omega  -27.00   40.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000 -180.0000 45

  3 omega   10.00   76.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000  -60.0000 44

  4 omega   26.00   86.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000    0.0000 40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0465111000
_diffrn_orient_matrix_UB_12      0.0085058000
_diffrn_orient_matrix_UB_13      -0.0764680000
_diffrn_orient_matrix_UB_21      -0.0163666000
_diffrn_orient_matrix_UB_22      -0.0268524000
_diffrn_orient_matrix_UB_23      -0.0183750000
_diffrn_orient_matrix_UB_31      -0.0255164000
_diffrn_orient_matrix_UB_32      0.0016800000
_diffrn_orient_matrix_UB_33      0.0907690000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4002
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.54
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(8)
_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     246
_refine_ls_number_reflns         2456
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0323P)^2^+0.2836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0889
_reflns_number_gt                2099
_reflns_number_total             2456
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01997_si_002.cif
_cod_data_source_block           wangchao0421
_cod_depositor_comments          'Adding full bibliography for 1529420.cif.'
_cod_database_code               1529420
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C12(H12A,H12B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_olex2_date_sample_data_collection 2015-04-21
_olex2_submission_special_instructions 'No special instructions were received'