Total Synthesis and Stereochemical Assignment of Delavatine A: Rh-Catalyzed Asymmetric Hydrogenation of Indene-Type Tetrasubstituted Olefins and Kinetic Resolution through Pd-Catalyzed Triflamide-Directed C-H Olefination.
Zhang, Zhongyin; Wang, Jinxin; Li, Jian; Yang, Fan; Liu, Guodu; Tang, Wenjun; He, Weiwei; Fu, Jian-Jun; Shen, Yun-Heng; Li, Ang; Zhang, Wei-Dong; Journal of the American Chemical Society 139 (2017) 5558–5567; doi:10.1021/jacs.7b01718

data_4126157
_publ_section_title
;
 Total Synthesis and Stereochemical Assignment of Delavatine A:
 Rh-Catalyzed Asymmetric Hydrogenation of Indene-Type Tetrasubstituted
 Olefins and Kinetic Resolution through Pd-Catalyzed Triflamide-Directed
 C-H Olefination.
;
_journal_issue                   15
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5558
_journal_page_last               5567
_journal_paper_doi               10.1021/jacs.7b01718
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H17 F4 N O4 S'
_chemical_formula_sum            'C16 H17 F4 N O4 S'
_chemical_formula_weight         395.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1711(2)
_cell_length_b                   8.6014(2)
_cell_length_c                   38.2861(12)
_cell_measurement_reflns_used    7250
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.47
_cell_measurement_theta_min      4.62
_cell_volume                     1702.92(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 VENTURE CMOS photon 100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            9467
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.498
_diffrn_reflns_theta_max         66.498
_diffrn_reflns_theta_min         2.308
_exptl_absorpt_coefficient_mu    2.302
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.141
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0712
_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^)+(0.1300P)^2^+0.0577P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1549
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2837
_reflns_number_total             2958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b01718_si_006.cif
_cod_data_source_block           P
_cod_database_code               4126157
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              5297
_shelx_hkl_checksum              81248