Enantioselective Indole N–H Functionalization Enabled by Addition of Carbene Catalyst to Indole Aldehyde at Remote Site
Yang, Xing; Luo, Guoyong; Zhou, Liejin; Liu, Bin; Zhang, Xiaolei; Gao, Hui; Jin, Zhichao; Chi, Yonggui Robin; ACS Catalysis  (2019) 10971–; doi:10.1021/acscatal.9b03163

data_4515254
_publ_section_title
;
 Enantioselective Indole N--H Functionalization Enabled by Addition of
 Carbene Catalyst to Indole Aldehyde at Remote Site
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              10971
_journal_paper_doi               10.1021/acscatal.9b03163
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H17 F3 N2 O4 S'
_chemical_formula_weight         510.47
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 97.442(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9025(7)
_cell_length_b                   8.5425(5)
_cell_length_c                   26.6115(16)
_cell_measurement_reflns_used    3658
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      25.5035
_cell_measurement_theta_min      3.3171
_cell_volume                     2232.2(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5700
_diffrn_reflns_theta_full        27.09
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_min         2.31
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.399
_refine_ls_abs_structure_details
;

No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     652
_refine_ls_number_reflns         5700
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0299P)^2^+1.1821P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                4534
_reflns_number_total             5700
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03163_si_002.cif
_cod_data_source_block           cyg281m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4515254
_shelx_res_checksum              64940
_shelx_hkl_checksum              57767