Nickel-catalysed enantioselective reaction of secondary phosphine oxides and activated vinylcyclopropanes.
Huang, Zhuo; Liu, Xu-Teng; Cui, Ranran; Zhang, Qing-Wei; Organic & biomolecular chemistry 21 (2023) 3096–3100; doi:10.1039/d3ob00389b

data_7159257
_publ_section_title
;
 Nickel-catalysed enantioselective reaction of secondary phosphine oxides
 and activated vinylcyclopropanes.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3096
_journal_page_last               3100
_journal_paper_doi               10.1039/d3ob00389b
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H31 O5 P'
_chemical_formula_sum            'C25 H31 O5 P'
_chemical_formula_weight         442.46
_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
_audit_creation_date             2022-05-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-06-10 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.37551(9)
_cell_length_b                   7.85484(12)
_cell_length_c                   56.3649(9)
_cell_measurement_reflns_used    4299
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.9170
_cell_measurement_theta_min      5.6960
_cell_volume                     2379.94(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4337
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.976
_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    -63.00  -6.00   0.30    4.00    --  -41.76 125.00  60.00  190
  2  \w     14.00 108.20   0.30    4.00    --   41.76  57.00 -60.00  314
  3  \w    139.00 166.00   0.30    8.00    --  106.05  77.00 -60.00   90
  4  \w     35.00 110.90   0.30    8.00    --  106.05-125.00-180.00  253
  5  \w     34.00 117.10   0.30    8.00    --  106.05 -45.00 150.00  277
  6  \w     61.00 166.00   0.30    8.00    --  106.05  15.00  30.00  350
  7  \w    148.00 178.00   0.30    8.00    --  106.05  77.00  60.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1015555000
_diffrn_orient_matrix_UB_12      0.1370542000
_diffrn_orient_matrix_UB_13      0.0169841000
_diffrn_orient_matrix_UB_21      0.0591408000
_diffrn_orient_matrix_UB_22      -0.1157641000
_diffrn_orient_matrix_UB_23      0.0213337000
_diffrn_orient_matrix_UB_31      0.2613365000
_diffrn_orient_matrix_UB_32      0.0794065000
_diffrn_orient_matrix_UB_33      0.0017934000
_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  0.0198
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -68
_diffrn_reflns_number            7177
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.871
_diffrn_reflns_theta_min         5.687
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.289
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.100
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
;
 Flack x determined using 1637 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.020(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4561
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0953
_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^)+(0.0980P)^2^+5.7324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2373
_refine_ls_wR_factor_ref         0.2409
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                4323
_reflns_number_total             4561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00389b2.cif
_cod_data_source_block           3n-pce_auto
_cod_depositor_comments
;
          Adding full bibliography for 7159257.cif.

2025-04-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C50 H62 O10 P2'
_cod_original_formula_weight         884.93
_cod_original_formula_moiety         '2(C25 H31 O5 P)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        2379.93(7)
_cod_database_code               7159257
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C20H20N2O2P1
_shelx_estimated_absorpt_t_max   0.783
_shelx_estimated_absorpt_t_min   0.739
_reflns_odcompleteness_completeness 98.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Restrained distances
 C21-O3
 1.4 with sigma of 0.01
 C21-C22 = C24-C25
 1.5 with sigma of 0.01
2. Rigid bond restraints
 O3, C21, C21, C22, C24, C25
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C20)
\\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq,
Uanis(C25) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(O2) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(O5) \\sim
Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of
0.04
4.a Ternary CH refined with riding coordinates:
 C19(H19)
4.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C13(H13A,H13B), C21(H21A,H21B), C18(H18A,H18B), C24(H24A,H24B)
4.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C5(H5), C8(H8), C3(H3), C11(H11), C10(H10), C6(H6), C9(H9), C2(H2),
 C16(H16), C17(H17)
4.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C22(H22A,H22B,H22C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              42936
_shelx_hkl_checksum              18034
_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 1.339
_oxdiff_exptl_absorpt_empirical_full_min 0.553