Chiral bidentate [N,S]-ferrocene ligands based on a thiazoline framework. Synthesis and use in palladium-catalyzed asymmetric allylic alkylation.
Sánchez-Rodríguez, E P; Hochberger-Roa, F; Corona-Sánchez, R; Barquera-Lozada, J E; Toscano, R. A.; Urrutigoïty, M; Gouygou, M.; Ortega-Alfaro, M C; López-Cortés, J G; Dalton transactions (Cambridge, England : 2003) 46 (2017) 1510–1519; doi:10.1039/c6dt04119a

data_1544970
_publ_section_title
;
 Chiral bidentate [N,S]-ferrocene ligands based on a thiazoline framework.
 Synthesis and use in palladium-catalyzed asymmetric allylic alkylation.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1510
_journal_page_last               1519
_journal_paper_doi               10.1039/c6dt04119a
_journal_volume                  46
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H19 Fe N S2'
_chemical_formula_sum            'C20 H19 Fe N S2'
_chemical_formula_weight         393.33
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-08-30 deposited with the CCDC.
2017-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   10.9404(2)
_cell_length_b                   10.9404(2)
_cell_length_c                   13.0885(3)
_cell_measurement_reflns_used    3557
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.22
_cell_measurement_theta_min      2.65
_cell_volume                     1356.71(5)
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_collection       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11659
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.235
_diffrn_reflns_theta_min         2.149
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.065
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       prism
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.438
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.187
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1604 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4457
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0227P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0626
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3785
_reflns_number_total             4457
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6dt04119a2.cif
_cod_data_source_block           Compound_5c
_cod_depositor_comments
'Adding full bibliography for 1544970--1544972.cif.'
_cod_original_cell_volume        1356.71(6)
_cod_database_code               1544970
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.653
_shelx_estimated_absorpt_t_max   0.826
_shelx_res_checksum              25058