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_1566164
_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         'C27 H28 Fe N P'
_chemical_formula_sum            'C27 H28 Fe N P'
_chemical_formula_weight         453.32
_chemical_melting_point          386.0(10)
_chemical_name_systematic
;
 {2-[(2R)-1-Methylpyrrolidin-2-yl]-(1R)-ferrocenyl
diphenylphosphine}
;
_chemical_properties_physical    none
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9001(4)
_cell_length_b                   14.5614(7)
_cell_length_c                   17.2157(8)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.21
_cell_measurement_theta_min      1.83
_cell_volume                     2231.12(18)
_computing_cell_refinement       'SMART software (Siemens, 1995)'
_computing_data_collection       'SMART software (Siemens, 1995)'
_computing_data_reduction        'SAINT software (Siemens, 1995)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Siemens SMART'
_diffrn_measurement_method       'CCD \w-scan'
_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  0.0566
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24554
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.207
_diffrn_reflns_theta_min         1.832
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent:  ethanol'
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 2522 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_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         8244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0477P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0934
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                6821
_reflns_number_total             8244
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            Tetrahedron-2021-90-132088.cif
_cod_data_source_block           3746
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '385-387' was changed to
'386.0(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_database_code               1566164
_shelx_estimated_absorpt_t_min   0.725
_shelx_estimated_absorpt_t_max   0.909
_shelx_res_checksum              25929
_shelx_hkl_checksum              67947