Catalytic Enantioselective Alkylation of Indoles with trans-4-Methylthio-β-Nitrostyrene
Méndez, Isabel; Ferrer, Carlos; Rodríguez, Ricardo; Lahoz, Fernando J.; García-Orduña, Pilar; Carmona, Daniel; ACS Omega 5 (2020) 27978–27989; doi:10.1021/acsomega.0c03485

data_4518150
_publ_section_title
;
 Catalytic Enantioselective Alkylation of Indoles with
 trans-4-Methylthio-\b-Nitrostyrene
;
_journal_issue                   43
_journal_name_full               'ACS Omega'
_journal_page_first              27978
_journal_page_last               27989
_journal_paper_doi               10.1021/acsomega.0c03485
_journal_volume                  5
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety
'C46 H50 Ir N O2 P2 S, 2(F6 Sb),1.5(C H2 Cl2), H2 O'
_chemical_formula_sum            'C47.5 H55 Cl3 F12 Ir N O3 P2 S Sb2'
_chemical_formula_weight         1551.97
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 93.038(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9760(18)
_cell_length_b                   46.000(8)
_cell_length_c                   10.9840(18)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.267
_cell_measurement_theta_min      2.284
_cell_volume                     5538.0(16)
_computing_cell_refinement
'SAINT+ in APEX3 v. 2017.3 (Bruker AXS, 2008)'
_computing_data_collection       'SMART in APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_data_reduction
'SAINT+ in APEX3 v. 2017.3 (Bruker AXS, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'XCIF program, PLATON(Spek, 1998)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX DUO system'
_diffrn_measurement_method       'narrow \w frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       59
_diffrn_reflns_limit_k_min       -59
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            59017
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.567
_diffrn_reflns_theta_min         1.328
_exptl_absorpt_coefficient_mu    3.687
_exptl_absorpt_correction_T_max  0.7955
_exptl_absorpt_correction_T_min  0.6212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'twinabs 2008/2'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_description       prism
_exptl_crystal_F_000             3020
_exptl_crystal_size_max          0.104
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.053
_refine_diff_density_max         1.574
_refine_diff_density_min         -0.837
_refine_diff_density_rms         0.132
_refine_ls_abs_structure_details
;
 Flack x determined using 7798 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1321
_refine_ls_number_reflns         25261
_refine_ls_number_restraints     115
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0366P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.947
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                21281
_reflns_number_total             25261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c03485_si_002.cif
_cod_data_source_block           cmpnd_4S
_cod_depositor_comments
;
Adding full bibliography for 4518149--4518150.cif.

2025-07-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C95 H110 Cl6 F24 Ir2 N2 O6 P4 S2 Sb4'
_cod_original_formula_weight         3103.94
_cod_original_formula_moiety
'2(C46 H50 Ir N O2 P2 S), 4(F6 Sb),3(C H2 Cl2), 2(H2 O)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        5537.9(16)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4518150
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              70985
_shelx_hkl_checksum              39853