Ferrocene-based <i>P</i>-chiral amidophosphinate: stereoselective synthesis and X-ray structural study.
Shekurov, Ruslan P.; Zagidullin, Almaz A.; Khrizanforov, Mikhail N.; Islamov, Daut R.; Gerasimova, Tatiana P.; Akhmatkhanova, Farida F.; Miluykov, Vasily A.; Dalton transactions (Cambridge, England : 2003)  (2022) –; doi:10.1039/d2dt02930h

data_7711847
_publ_section_title
;
 Ferrocene-based <i>P</i>-chiral amidophosphinate: stereoselective
 synthesis and X-ray structural study.
;
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_paper_doi               10.1039/d2dt02930h
_journal_year                    2022
_chemical_formula_moiety         'C24 H33 Fe N2 O P'
_chemical_formula_sum            'C24 H33 Fe N2 O P'
_chemical_formula_weight         452.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-14
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2021-05-24 deposited with the CCDC.	2022-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.5750(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.55720(10)
_cell_length_b                   11.51440(10)
_cell_length_c                   18.7369(2)
_cell_measurement_reflns_used    17904
_cell_measurement_temperature    99.9(9)
_cell_measurement_theta_max      76.1830
_cell_measurement_theta_min      4.4860
_cell_volume                     2257.78(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(9)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     34.00  64.00   0.50    0.12    --   47.45  57.00 -60.00   60
  2  \w     36.00  73.00   0.50    0.12    --   47.45  37.00 -90.00   74
  3  \w     51.00  76.00   0.50    0.12    --   47.45  60.00 144.00   50
  4  \w     74.00 119.00   0.50    0.12    --   47.45 125.00   0.00   90
  5  \w     74.00 118.00   0.50    0.12    --   47.45 125.00 -30.00   88
  6  \w     84.00 111.00   0.50    0.12    --   47.45 125.00  30.00   54
  7  \w     75.00 120.00   0.50    0.12    --   47.45 125.00-180.00   90
  8  \w     76.00 116.00   0.50    0.12    --   47.45 125.00-120.00   80
  9  \w     84.00 110.00   0.50    0.49    --  105.86  77.00-150.00   52
 10  \w     93.00 119.00   0.50    0.49    --  105.86  61.00-120.00   52
 11  \w    133.00 158.00   0.50    0.49    --  105.86  45.00 -90.00   50
 12  \w    153.00 178.00   0.50    0.49    --  105.86  15.00-120.00   50
 13  \w     93.00 119.00   0.50    0.49    --  105.86  45.00 -90.00   52
 14  \w     97.00 170.00   0.50    0.49    --  105.86  15.00 -60.00  146
 15  \w     93.00 152.00   0.50    0.49    --  105.86  15.00   0.00  118
 16  \w     99.00 124.00   0.50    0.49    --  105.86  61.00  60.00   50
 17  \w    134.00 159.00   0.50    0.49    --  105.86  60.00 144.00   50
 18  \w    135.00 168.00   0.50    0.49    --  105.86  61.00  60.00   66
 19  \w     93.00 120.00   0.50    0.49    --  105.86  15.00-120.00   54
 20  \w     35.00  62.00   0.50    0.49    --  105.86 -60.00   4.00   54
 21  \w     33.00  70.00   0.50    0.49    --  105.86 -61.00  30.00   74
 22  \w     38.00  71.00   0.50    0.49    --  105.86 -61.00 120.00   66
 23  \w     40.00  71.00   0.50    0.49    --  105.86 -61.00 150.00   62
 24  \w     33.00 105.00   0.50    0.49    --  105.86 -77.00  30.00  144
 25  \w    -24.00  60.00   0.50    0.12    --   47.45 -60.00   4.00  168
 26  \w     34.00  60.00   0.50    0.49    --  105.86 -61.00-150.00   52
 27  \w     33.00  71.00   0.50    0.49    --  105.86 -61.00-180.00   76
 28  \w     64.00 110.00   0.50    0.49    --  105.86-125.00 -90.00   92
 29  \w     33.00  99.00   0.50    0.49    --  105.86 -94.00   0.00  132
 30  \w    -49.00  17.00   0.50    0.12    --  -47.45  60.00 144.00  132
 31  \w    -27.00  26.00   0.50    0.12    --  -47.45  19.00 120.00  106
 32  \w    -68.00 -34.00   0.50    0.49    -- -105.86  60.00 144.00   68
 33  \w    -70.00 -33.00   0.50    0.49    -- -105.86  61.00 120.00   74
 34  \w    -61.00 -36.00   0.50    0.49    -- -105.86  61.00   0.00   50
 35  \w    -71.00 -40.00   0.50    0.49    -- -105.86  61.00-180.00   62
 36  \w   -109.00 -83.00   0.50    0.49    -- -105.86 -77.00 -60.00   52
 37  \w   -118.00 -89.00   0.50    0.49    -- -105.86 -61.00 -90.00   58
 38  \w   -175.00-149.00   0.50    0.49    -- -105.86 -77.00 -60.00   52
 39  \w   -169.00-143.00   0.50    0.49    -- -105.86 -61.00 -90.00   52
 40  \w   -143.00-118.00   0.50    0.49    -- -105.86 -61.00 -60.00   50
 41  \w   -114.00 -89.00   0.50    0.49    -- -105.86 -61.00 -60.00   50
 42  \w   -174.00-131.00   0.50    0.49    -- -105.86 -60.00   4.00   86
 43  \w   -174.00-134.00   0.50    0.49    -- -105.86 -43.00-135.26   80
 44  \w   -177.00-141.00   0.50    0.49    -- -105.86 -45.00-150.00   72
 45  \w   -142.00 -94.00   0.50    0.49    -- -105.86 -45.00-120.00   96
 46  \w   -127.00 -97.00   0.50    0.49    -- -105.86 -45.00-150.00   60
 47  \w   -117.00 -92.00   0.50    0.49    -- -105.86 -43.00-135.26   50
 48  \w   -131.00 -93.00   0.50    0.49    -- -105.86 -30.00-150.00   76
 49  \w   -125.00 -93.00   0.50    0.49    -- -105.86 -30.00 -90.00   64
 50  \w   -122.00 -63.00   0.50    0.12    --  -47.45 -19.00-180.00  118
 51  \w    -87.00 -47.00   0.50    0.12    --  -47.45 -60.00   4.00   80
 52  \w   -144.00 -95.00   0.50    0.49    -- -105.86 -15.00  60.00   98
 53  \w   -169.00-100.00   0.50    0.49    -- -105.86 -30.00  60.00  138
 54  \w   -113.00 -88.00   0.50    0.49    -- -105.86 -85.00 -70.01   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1334563000
_diffrn_orient_matrix_UB_12      -0.0259627000
_diffrn_orient_matrix_UB_13      -0.0209087000
_diffrn_orient_matrix_UB_21      -0.0588656000
_diffrn_orient_matrix_UB_22      -0.0907924000
_diffrn_orient_matrix_UB_23      -0.0550764000
_diffrn_orient_matrix_UB_31      -0.0198393000
_diffrn_orient_matrix_UB_32      0.0947253000
_diffrn_orient_matrix_UB_33      -0.0584299000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31490
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.713
_diffrn_reflns_theta_min         4.518
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.149
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_T_min  0.343
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.331
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.117
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+1.2304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0803
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4491
_reflns_number_total             4692
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt02930h2.cif
_cod_data_source_block           zag507_corr
_cod_database_code               7711847
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C24H33FeN2OP
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C25(H25), C10(H10), C29(H29), C14(H14), C12(H12), C27(H27),
 C15(H15), C11(H11), C13(H13), C26(H26), C28(H28)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C23(H23A,H23B,H23C), C18(H18A,H18B,
 H18C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              97953
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.287
_oxdiff_exptl_absorpt_empirical_full_min 0.585