Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines.
Vidal, Xandro; Mascareñas, José L; Gulías, Moisés; Journal of the American Chemical Society 141 (2019) 1862–1866; doi:10.1021/jacs.8b12636

data_4127926
_publ_section_title
;
 Palladium-Catalyzed, Enantioselective Formal Cycloaddition between
 Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched
 Isoquinolines.
;
_journal_issue                   5
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1862
_journal_page_last               1866
_journal_paper_doi               10.1021/jacs.8b12636
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C18 H22 F3 N O2 S'
_chemical_formula_sum            'C18 H22 F3 N O2 S'
_chemical_formula_weight         373.42
_chemical_name_common            18MCD016
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 100.483(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9817(10)
_cell_length_b                   8.5549(9)
_cell_length_c                   10.6135(10)
_cell_measurement_reflns_used    9431
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      32.7788
_cell_measurement_theta_min      2.3807
_cell_volume                     891.19(15)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker APEX3 software'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_radiation_monochromator  'Incoatec HeliosTM multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16431
_diffrn_reflns_theta_full        32.85
_diffrn_reflns_theta_max         32.85
_diffrn_reflns_theta_min         3.08
_diffrn_source                   'Incoatec high brillance I\muS microsource'
_diffrn_source_type              'INCOATEC microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.247
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.444
_refine_ls_abs_structure_details
;

Flack x determined using 2304 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         6516
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0426P)^2^+0.0940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0906
_reflns_number_gt                5640
_reflns_number_total             6516
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b12636_si_002.cif
_cod_data_source_block           18MCD016
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4127926
_shelx_res_checksum              24208
_shelx_hkl_checksum              91719