The preparation of ferrocene-containing phosphinamine ligands possessing central and planar chirality and their application in palladium-catalysed allylic substitution
Meaney, Keith; Goddard, Richard; Bronger, Raymond P.J.; Guiry, Patrick J.; Tetrahedron 90 (2021) 132088–; doi:10.1016/j.tet.2021.132088

data_1566165
_publ_section_title
;
 The preparation of ferrocene-containing phosphinamine ligands possessing
 central and planar chirality and their application in palladium-catalysed
 allylic substitution
;
_journal_name_full               Tetrahedron
_journal_page_first              132088
_journal_paper_doi               10.1016/j.tet.2021.132088
_journal_volume                  90
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C30 H36 Fe N P Si'
_chemical_formula_sum            'C30 H36 Fe N P Si'
_chemical_formula_weight         525.51
_chemical_melting_point          400.0(10)
_chemical_name_systematic
;
 2-[(2R)-1-methylpyrrolidin-2-yl]-
 (3S)-trimethylsilyl-(1R)-ferrocenyldiphenylphosphine
;
_chemical_properties_physical    none
_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     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 98.5640(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.23440(10)
_cell_length_b                   17.3214(3)
_cell_length_c                   22.1734(5)
_cell_measurement_reflns_used    32078
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      1.0
_cell_volume                     2747.57(9)
_computing_cell_refinement       'Denzo / Scalepack (Otwinowski 1997)'
_computing_data_collection       'Collect software (Nonius, 1998)'
_computing_data_reduction        'Denzo / Scalepack (Otwinowski 1997)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2014)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD \w-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.3 mm focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.1686
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15027
_diffrn_reflns_point_group_measured_fraction_full 0.901
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.743
_diffrn_reflns_theta_min         5.474
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  0.9732
_exptl_absorpt_correction_T_min  0.9573
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            orange-yellow
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             1112
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent:  ethanol'
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details
;
 Flack x determined using 2007 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         10191
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1390
_refine_ls_R_factor_gt           0.0791
_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^)+5.2389P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1506
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.809
_reflns_Friedel_fraction_max     0.755
_reflns_number_gt                6667
_reflns_number_total             10191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            Tetrahedron-2021-90-132088.cif
_cod_data_source_block           4033
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '399-401' was changed to
'400.0(10)' -- the average value was taken and precision was
estimated.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1566165
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              3235
_shelx_hkl_checksum              39870