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_7711846
_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_absolute_configuration ad
_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           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     dual
_audit_creation_date             2022-11-01
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-01 deposited with the CCDC.	2022-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.0260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.43980(10)
_cell_length_b                   11.36250(10)
_cell_length_c                   19.06660(10)
_cell_measurement_reflns_used    44456
_cell_measurement_temperature    99.9(10)
_cell_measurement_theta_max      75.7730
_cell_measurement_theta_min      2.3010
_cell_volume                     2258.57(3)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_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     29.00  55.00   0.50    0.10    --   52.00  77.00  72.98   52
  2  \w     33.00  59.00   0.50    0.10    --   56.00  77.00 111.73   52
  3  \w     96.00 128.00   0.50    0.10    --   56.00  77.00 111.73   64
  4  \w     84.00 125.00   0.50    0.10    --   52.00  77.00  72.98   82
  5  \w     45.00  74.00   0.50    0.10    --   68.00  77.00  46.57   58
  6  \w     42.00  68.00   0.50    0.10    --   64.00  77.00  14.66   52
  7  \w     45.00  71.00   0.50    0.10    --   68.00  77.00  82.88   52
  8  \w    103.00 129.00   0.50    0.10    --   68.00  77.00  46.57   52
  9  \w    115.00 140.00   0.50    0.10    --   68.00  75.00 -24.97   50
 10  \w     37.00  86.00   0.50    0.10    --   60.00  77.00 -31.11   98
 11  \w     46.00  72.00   0.50    0.10    --   68.00  77.00 -58.84   52
 12  \w     46.00  73.00   0.50    0.10    --   68.00  75.00 -81.45   54
 13  \w     46.00  72.00   0.50    0.10    --   68.00  75.00 -24.97   52
 14  \w     34.00  64.00   0.50    0.10    --   56.00  75.00 -93.22   60
 15  \w     69.00  95.00   0.50    0.10    --   56.00  75.00 -93.22   52
 16  \w     33.00  81.00   0.50    0.10    --   56.00  77.00-177.51   96
 17  \w     42.00  67.00   0.50    0.10    --   64.00  75.00-147.53   50
 18  \w     46.00  77.00   0.50    0.10    --   64.00  71.00-128.74   62
 19  \w     52.00  78.00   0.50    0.10    --   72.00  70.00  23.26   52
 20  \w     39.00  75.00   0.50    0.10    --   60.00  72.00  15.14   72
 21  \w     45.00  97.00   0.50    0.10    --   47.45  37.00  30.00  104
 22  \w     44.00  72.00   0.50    0.10    --   64.00  73.00 146.14   56
 23  \w     91.00 135.00   0.50    0.10    --   64.00  73.00 146.14   88
 24  \w    -61.00 -36.00   0.50    0.20    -- -105.86  61.00  60.00   50
 25  \w    -76.00 -35.00   0.50    0.20    -- -105.86 105.00 115.00   82
 26  \w   -122.00 -83.00   0.50    0.20    -- -105.86 140.00 167.13   78
 27  \w   -106.00 -80.00   0.50    0.20    -- -105.86 105.00 115.00   52
 28  \w   -111.00 -71.00   0.50    0.20    -- -105.86 125.00  60.00   80
 29  \w    -70.00 -34.00   0.50    0.20    -- -105.86  61.00 -90.00   72
 30  \w    -83.00 -19.00   0.50    0.10    --  -47.45 105.00 115.00  128
 31  \w    -41.00 -15.00   0.50    0.10    --    8.00 129.00 112.67   52
 32  \w     -9.00  16.00   0.50    0.10    --   24.00 101.00 125.99   50
 33  \w      6.00  31.00   0.50    0.10    --   36.00  93.00 138.02   50
 34  \w     17.00  42.00   0.50    0.10    --   44.00  87.00 178.04   50
 35  \w     17.00  42.00   0.50    0.10    --   44.00  86.00  16.23   50
 36  \w    -27.00  -2.00   0.50    0.10    --   12.00 109.00 -64.29   50
 37  \w     -5.00  26.00   0.50    0.10    --   24.00  97.00-100.74   62
 38  \w     12.00  37.00   0.50    0.10    --   40.00  88.00-114.32   50
 39  \w     17.00  42.00   0.50    0.10    --   44.00  86.00 -14.38   50
 40  \w    125.00 151.00   0.50    0.20    --  105.86 105.00 115.00   52
 41  \w     71.00  96.00   0.50    0.20    --  105.86 -77.00-150.00   50
 42  \w     35.00  60.00   0.50    0.20    --  105.86 -77.00-150.00   50
 43  \w    -23.00  61.00   0.50    0.10    --   47.45 -57.00  60.00  168
 44  \w     33.00 100.00   0.50    0.20    --  105.86 -77.00  90.00  134
 45  \w     34.00 105.00   0.50    0.20    --  105.86 -77.00   0.00  142
 46  \w     35.00  60.00   0.50    0.20    --  105.86 -94.00 -30.00   50
 47  \w     59.00 106.00   0.50    0.20    --  105.86-105.00  14.00   94
 48  \w     36.00  98.00   0.50    0.20    --  105.86 -94.00 -60.00  124
 49  \w     36.00 104.00   0.50    0.20    --  105.86 -94.00-120.00  136
 50  \w     35.00 105.00   0.50    0.20    --  105.86-125.00-150.00  140
 51  \w     70.00 103.00   0.50    0.20    --  105.86 -94.00 -30.00   66
 52  \w     12.00  57.00   0.50    0.10    --   47.45-105.00  14.00   90
 53  \w    -92.00 -67.00   0.50    0.20    --  -84.00 -62.00 -73.90   50
 54  \w   -125.00 -81.00   0.50    0.20    -- -104.00 -79.00 -67.73   88
 55  \w   -162.00-111.00   0.50    0.20    --  -92.00 -77.00 -62.81  102
 56  \w   -177.00-152.00   0.50    0.20    -- -104.00 -79.00 -67.73   50
 57  \w   -168.00 -74.00   0.50    0.20    --  -96.00 -77.00 -45.40  188
 58  \w   -160.00 -73.00   0.50    0.20    --  -96.00 -77.00-104.96  174
 59  \w   -168.00 -73.00   0.50    0.20    --  -96.00 -77.00-125.17  190
 60  \w    -91.00 -65.00   0.50    0.20    --  -88.00 -77.00 -91.01   52
 61  \w   -101.00 -69.00   0.50    0.20    --  -92.00 -77.00 -62.81   64
 62  \w    -79.00 -53.00   0.50    0.10    --  -76.00 -76.00 -93.43   52
 63  \w   -148.00 -73.00   0.50    0.20    --  -96.00 -76.00  19.05  150
 64  \w   -162.00-136.00   0.50    0.20    --  -96.00 -76.00  77.73   52
 65  \w   -176.00 -83.00   0.50    0.20    -- -105.86 -76.00 136.66  186
 66  \w   -101.00 -70.00   0.50    0.20    --  -92.00 -74.00 177.90   62
 67  \w    -99.00 -69.00   0.50    0.20    --  -92.00 -76.00 146.23   60
 68  \w   -130.00-105.00   0.50    0.20    --  -92.00 -76.00 146.23   50
 69  \w   -163.00-106.00   0.50    0.20    --  -92.00 -74.00 177.90  114
 70  \w    -84.00 -58.00   0.50    0.20    --  -80.00 -74.00 149.28   52
 71  \w    -80.00 -54.00   0.50    0.10    --  -76.00 -74.00 100.39   52
 72  \w   -100.00 -74.00   0.50    0.20    --  -96.00 -76.00  77.73   52
 73  \w    -68.00 -38.00   0.50    0.10    --  -60.00 -74.00  18.43   60
 74  \w   -113.00 -71.00   0.50    0.20    --  -92.00 -73.00 157.27   84
 75  \w   -165.00 -70.00   0.50    0.20    --  -92.00 -75.00  37.09  190
 76  \w    -85.00 -59.00   0.50    0.20    --  -80.00 -73.00  39.21   52
 77  \w    -93.00 -60.00   0.50    0.20    --  -80.00 -73.00 175.26   66
 78  \w   -154.00-128.00   0.50    0.20    --  -92.00 -73.00 157.27   52
 79  \w   -108.00 -66.00   0.50    0.20    --  -88.00 -74.00 -10.02   84
 80  \w    -86.00 -60.00   0.50    0.20    --  -80.00 -73.00  93.72   52
 81  \w   -145.00-114.00   0.50    0.20    --  -92.00 -73.00-100.84   62
 82  \w    -83.00 -58.00   0.50    0.20    --  -80.00 -74.00-155.04   50
 83  \w    -78.00 -46.00   0.50    0.10    --  -68.00 -74.00-140.40   64
 84  \w    -98.00 -72.00   0.50    0.20    --  -92.00 -73.00-100.84   52
 85  \w    -85.00 -59.00   0.50    0.20    --  -80.00 -73.00 -42.04   52
 86  \w    -99.00 -67.00   0.50    0.20    --  -88.00 -73.00 -22.22   64
 87  \w   -140.00-115.00   0.50    0.20    --  -88.00 -73.00 -22.22   50
 88  \w   -149.00-123.00   0.50    0.20    --  -80.00 -70.00-144.87   52
 89  \w    -85.00 -59.00   0.50    0.20    --  -80.00 -72.00  77.45   52
 90  \w    -73.00 -48.00   0.50    0.10    --  -68.00 -71.00 115.92   50
 91  \w    -76.00 -51.00   0.50    0.10    --  -72.00 -72.00 158.84   50
 92  \w   -161.00 -67.00   0.50    0.20    --  -88.00 -72.00 125.81  188
 93  \w   -164.00 -73.00   0.50    0.20    --  -92.00 -70.00  48.31  182
 94  \w   -163.00 -79.00   0.50    0.20    --  -96.00 -67.00 -32.42  168
 95  \w    -91.00 -60.00   0.50    0.20    --  -80.00 -70.00-144.87   62
 96  \w   -167.00 -77.00   0.50    0.20    --  -96.00 -67.00-171.45  180
 97  \w   -146.00-120.00   0.50    0.20    --  -96.00 -68.00-148.78   52
 98  \w   -117.00 -77.00   0.50    0.20    --  -96.00 -68.00-148.78   80
 99  \w   -142.00 -78.00   0.50    0.20    --  -96.00 -65.00  74.65  128
100  \w    -94.00 -66.00   0.50    0.20    --  -84.00 -65.00 100.21   56
101  \w   -103.00 -78.00   0.50    0.20    --  -96.00 -64.00 100.04   50
102  \w   -164.00 -80.00   0.50    0.20    --  -96.00 -64.00  86.12  168
103  \w   -157.00-131.00   0.50    0.20    --  -96.00 -64.00 100.04   52
104  \w   -135.00 -98.00   0.50    0.20    -- -105.86-105.00  14.00   74
105  \w    -41.00 -14.00   0.50    0.10    --  -40.00 -83.00 -81.86   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0858
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       12
_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            65402
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.718
_diffrn_reflns_theta_min         2.321
_exptl_absorpt_coefficient_mu    6.147
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.137
_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    1.330
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.273
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.006(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         9084
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0598P)^2^+1.1978P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                8740
_reflns_number_total             9084
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt02930h2.cif
_cod_data_source_block           mil462_corr
_cod_database_code               7711846
_shelx_shelxl_version_number     2019/2
_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. Rigid body (RIGU) restrains
 C22B, C23B, C22C, C23C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Sof(C22C)=Sof(H22C)=Sof(H22D)=Sof(C23C)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(1)
 Sof(C22B)=Sof(H22A)=Sof(H22B)=Sof(C23B)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C16A(H16A), C16B(H16B)
4.b Secondary CH2 refined with riding coordinates:
 C20A(H20C,H20D), C20B(H20A,H20B), C22A(H22E,H22F), C22B(H22A,H22B), C22C(H22C,
 H22D)
4.c Aromatic/amide H refined with riding coordinates:
 C29A(H29A), C11A(H11A), C8A(H8A), C25A(H25A), C9B(H9B), C29B(H29B), C9A(H9A),
 C28A(H28A), C26A(H26A), C10A(H10A), C12A(H12A), C11B(H11B), C10B(H10B),
 C8B(H8B), C14A(H14A), C15A(H15A), C12B(H12B), C14B(H14B), C13A(H13A),
 C27A(H27A), C15B(H15B), C28B(H28B), C13B(H13B), C25B(H25B), C27B(H27B),
 C26B(H26B)
4.d Idealised Me refined as rotating group:
 C17A(H17D,H17E,H17F), C18A(H18D,H18E,H18F), C17B(H17A,H17B,H17C), C19A(H19D,
 H19E,H19F), C23A(H23G,H23H,H23I), C19B(H19A,H19B,H19C), C21A(H21D,H21E,H21F),
 C21B(H21A,H21B,H21C), C23B(H23A,H23B,H23C), C18B(H18A,H18B,H18C), C23C(H23D,
 H23E,H23F)
;
_shelx_res_checksum              96475
_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
;