Stereoselective Synthesis of all Possible Phosferrox Ligand Diastereoisomers Displaying Three Elements of Chirality: Stereochemical Optimization for Asymmetric Catalysis.
Arthurs, Ross A.; Hughes, David L.; Richards, Christopher John; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03342

data_4038058
_publ_section_title
;
 Stereoselective Synthesis of all Possible Phosferrox Ligand
 Diastereoisomers Displaying Three Elements of Chirality: Stereochemical
 Optimization for Asymmetric Catalysis.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03342
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C27 H26 Fe N O P'
_chemical_formula_structural     'Cp Fe C5H3-(cyclo-CNCHMeCH2O),2-PPh(tol)'
_chemical_formula_sum            'C27 H26 Fe N O P'
_chemical_formula_weight         467.31
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-05-17 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                74.336(3)
_cell_angle_beta                 74.502(4)
_cell_angle_gamma                87.802(3)
_cell_formula_units_Z            1
_cell_length_a                   8.0680(3)
_cell_length_b                   8.1779(3)
_cell_length_c                   9.0160(4)
_cell_measurement_reflns_used    6383
_cell_measurement_temperature    140.0(8)
_cell_measurement_theta_max      32.5720
_cell_measurement_theta_min      3.6770
_cell_volume                     551.58(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976 and Farrugia, 2012)'
_computing_publication_material
'SHELXL-2014/7 (Sheldrick, 2015b) and WINGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      140(1)
_diffrn_detector_area_resol_mean 16.0050
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 3/Sapphire3 CCD'
_diffrn_measurement_method       'Thin slice \f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8378
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         3.038
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
 Empirical absorption correction using spherical harmonics,
  implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange-red
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 2238 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5019
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0282P)^2^+0.4338P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0823
_reflns_Friedel_coverage         0.975
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                4852
_reflns_number_total             5019
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03342_si_002.cif
_cod_data_source_block           rossa21
_cod_database_code               4038058
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              51620
_shelx_hkl_checksum              18878