A route to asymmetrically substituted secondary phosphines
Koschabek, Sarah; El Sayed Moussa, Mehdi; Riesinger, Christoph; Balazs, Gabor; Scheer, Manfred; Chemical Communications  (2026) –; doi:10.1039/D6CC01138A

data_7135678
_publ_section_title
;
 A route to asymmetrically substituted secondary phosphines.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7979
_journal_page_last               7983
_journal_paper_doi               10.1039/d6cc01138a
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C14 H25 Fe P5'
_chemical_formula_sum            'C14 H25 Fe P5'
_chemical_formula_weight         404.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-11-09
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7317)
;
_audit_update_record
;
2026-02-02 deposited with the CCDC.	2026-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.1030(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.00330(10)
_cell_length_b                   15.17660(10)
_cell_length_c                   12.33030(10)
_cell_measurement_reflns_used    17177
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      66.5240
_cell_measurement_theta_min      4.1490
_cell_volume                     1968.01(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.2047
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -89.00 -53.00   1.00    1.75    --  -43.23 -43.00-141.00   36
  2  \w    -19.00  27.00   1.00    1.75    --   43.23 -43.00-141.00   46
  3  \w     26.00 113.00   1.00    1.75    --   43.23  43.00  10.00   87
  4  \w     85.00 110.00   1.00    7.00    --   86.50  43.00  10.00   25
  5  \w    -56.00 -31.00   1.00    7.00    --  -90.00  43.00  10.00   25
  6  \w   -113.00 -87.00   1.00    7.00    --  -90.00  43.00  10.00   26
  7  \w   -150.00-113.00   1.00    7.00    --  -90.00 -43.00-141.00   37
  8  \w    -43.00 -17.00   1.00    1.75    --  -43.23  43.00  10.00   26
  9  \w    -93.00 -28.00   1.00    1.75    --  -43.23 125.00-180.00   65
 10  \w     18.00 111.00   1.00    1.75    --   43.23  57.00 120.00   93
 11  \w     62.00  88.00   1.00    7.00    --   86.50  61.00 150.00   26
 12  \w   -137.00-111.00   1.00    7.00    --  -90.00 -30.00 120.00   26
 13  \w   -155.00-108.00   1.00    7.00    --  -90.00-125.00 -30.00   47
 14  \w   -100.00 -63.00   1.00    7.00    --  -90.00 -61.00  60.00   37
 15  \w    -99.00 -61.00   1.00    7.00    --  -90.00 -68.00 113.56   38
 16  \w   -159.00-133.00   1.00    7.00    --  -90.00 -61.00  60.00   26
 17  \w   -163.00-103.00   1.00    7.00    --  -90.00 -77.00   0.00   60
 18  \w   -129.00-103.00   1.00    7.00    --  -90.00 -45.00-180.00   26
 19  \w    -64.00 -20.00   1.00    7.00    --  -90.00  45.00 120.00   44
 20  \w   -170.00-144.00   1.00    7.00    --  -90.00 -94.00 -60.00   26
 21  \w   -103.00 -77.00   1.00    7.00    --  -90.00  45.00-150.00   26
 22  \w   -160.00 -66.00   1.00    7.00    --  -90.00 -43.00 103.50   94
 23  \w   -159.00-133.00   1.00    7.00    --  -90.00 -68.00 113.56   26
 24  \w   -103.00 -69.00   1.00    7.00    --  -90.00 -45.00  22.22   34
 25  \w    -94.00 -64.00   1.00    7.00    --  -90.00 -61.00  30.00   30
 26  \w   -129.00-103.00   1.00    7.00    --  -90.00  15.00  60.00   26
 27  \w    -68.00 -16.00   1.00    7.00    --  -90.00  15.00  60.00   52
 28  \w   -116.00 -68.00   1.00    7.00    --  -90.00  61.00-150.00   48
 29  \w    -46.00 -21.00   1.00    7.00    --  -90.00  61.00-150.00   25
 30  \w    -42.00 -17.00   1.00    7.00    --  -90.00  30.00 -30.00   25
 31  \w   -100.00 -75.00   1.00    7.00    --  -90.00 -45.00-180.00   25
 32  \w   -116.00 -90.00   1.00    7.00    --  -90.00 -68.00-124.80   26
 33  \w    -91.00 -66.00   1.00    7.00    --  -90.00 -61.00 120.00   25
 34  \w   -104.00 -67.00   1.00    7.00    --  -90.00 -68.00 -76.56   37
 35  \w   -132.00 -90.00   1.00    7.00    --  -90.00 -15.00-120.00   42
 36  \w    -86.00 -56.00   1.00    7.00    --  -90.00 -15.00-120.00   30
 37  \w   -121.00 -96.00   1.00    7.00    --  -90.00 -45.00  60.00   25
 38  \w   -110.00 -66.00   1.00    7.00    --  -90.00 -61.00  90.00   44
 39  \w   -157.00 -96.00   1.00    7.00    --  -90.00 -45.00 150.00   61
 40  \w   -143.00-118.00   1.00    7.00    --  -90.00 -45.00  90.00   25
 41  \w    -65.00 -39.00   1.00    7.00    --  -90.00  46.00-177.02   26
 42  \w    -97.00 -44.00   1.00    7.00    --  -90.00  45.00 -90.00   53
 43  \w    -91.00 -22.00   1.00    7.00    --  -90.00  61.00  60.00   69
 44  \w   -128.00 -61.00   1.00    7.00    --  -90.00 -15.00 -30.00   67
 45  \w   -122.00 -97.00   1.00    7.00    --  -90.00-125.00   0.00   25
 46  \w   -161.00-120.00   1.00    7.00    --  -90.00-125.00 120.00   41
 47  \w   -161.00-136.00   1.00    7.00    --  -90.00 -95.00 130.24   25
 48  \w   -112.00 -27.00   1.00    7.00    --  -90.00 125.00 -90.00   85
 49  \w   -116.00 -91.00   1.00    7.00    --  -90.00 -53.00 -85.56   25
 50  \w   -150.00-124.00   1.00    7.00    --  -90.00 -51.00 -82.72   26
 51  \w   -107.00 -82.00   1.00    7.00    --  -90.00 -45.00-150.00   25
 52  \w   -149.00-119.00   1.00    7.00    --  -90.00 -61.00-180.00   30
 53  \w   -111.00 -86.00   1.00    7.00    --  -90.00  30.00 -30.00   25
 54  \w    -73.00 -48.00   1.00    7.00    --  -90.00  45.00-150.00   25
 55  \w    -98.00 -72.00   1.00    7.00    --  -90.00  30.00 120.00   26
 56  \w    -52.00 -23.00   1.00    7.00    --  -90.00  30.00 120.00   29
 57  \w   -119.00 -94.00   1.00    7.00    --  -90.00 -30.00  30.00   25
 58  \w   -138.00-113.00   1.00    7.00    --  -90.00 -77.00 -90.00   25
 59  \w   -118.00 -93.00   1.00    7.00    --  -90.00  77.00-180.00   25
 60  \w    -48.00 -10.00   1.00    7.00    --  -90.00   0.00 -60.00   38
 61  \w   -141.00-116.00   1.00    7.00    --  -90.00-125.00  30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dualflex, TitanS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0763427000
_diffrn_orient_matrix_UB_12      0.0224532000
_diffrn_orient_matrix_UB_13      -0.1230262000
_diffrn_orient_matrix_UB_21      0.0985402000
_diffrn_orient_matrix_UB_22      -0.0495421000
_diffrn_orient_matrix_UB_23      -0.0436325000
_diffrn_orient_matrix_UB_31      -0.0768857000
_diffrn_orient_matrix_UB_32      -0.0857298000
_diffrn_orient_matrix_UB_33      -0.0069833000
_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  0.1043
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            31700
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.639
_diffrn_reflns_theta_max         66.639
_diffrn_reflns_theta_min         4.204
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0949P)^2^+1.0109P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1306
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3288
_reflns_number_total             3488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc01138a2.cif
_cod_data_source_block           sk190_auto
_cod_depositor_comments          'Adding full bibliography for 7135678.cif.'
_cod_database_code               7135678
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H25 Fe P5'
_cell_oxdiff_angle_alpha         89.996(2)
_cell_oxdiff_angle_beta          107.100(2)
_cell_oxdiff_angle_gamma         89.984(2)
_cell_oxdiff_length_a            11.0053(3)
_cell_oxdiff_length_b            15.1736(4)
_cell_oxdiff_length_c            12.3302(3)
_cell_oxdiff_measurement_reflns_used 17177
_cell_oxdiff_volume              1968.00(8)
_shelx_estimated_absorpt_t_max   0.638
_shelx_estimated_absorpt_t_min   0.125
_diffrn_oxdiff_digest_hkl
;
01c42e8ec956f9e732ae9e002ef97583842f35
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C3(H3A,H3B,H3C),
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C2(H2A,H2B,H2C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              21340
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.445
_oxdiff_exptl_absorpt_empirical_full_min 0.549