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_1544971
_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         'C14 H17 Fe N O S'
_chemical_formula_sum            'C14 H17 Fe N O S'
_chemical_formula_weight         303.19
_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   mixed
_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                90
_cell_formula_units_Z            4
_cell_length_a                   7.6132(8)
_cell_length_b                   10.3234(11)
_cell_length_c                   17.0932(19)
_cell_measurement_reflns_used    7812
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      2.30
_cell_volume                     1343.4(3)
_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 0.993
_diffrn_measured_fraction_theta_max 0.992
_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  0.0534
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11096
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.384
_diffrn_reflns_theta_min         2.383
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.264
_exptl_absorpt_correction_T_max  0.8154
_exptl_absorpt_correction_T_min  0.5903
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(Sheldrick, 2000)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.476
_exptl_crystal_size_mid          0.422
_exptl_crystal_size_min          0.168
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 912 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     233
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0234
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0254P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0522
_refine_ls_wR_factor_ref         0.0529
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2310
_reflns_number_total             2462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6dt04119a2.cif
_cod_data_source_block           Compound_3
_cod_depositor_comments
'Adding full bibliography for 1544970--1544972.cif.'
_cod_database_code               1544971
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.584
_shelx_estimated_absorpt_t_max   0.816
_shelx_res_checksum              39957