CAMDOL-enabled diastereoselective synthesis of α-substituted phosphonates.
Huang, Yu; Zhang, Yulong; Pan, Li; Wu, Qian; Li, Ning; Shi, Enxue; Xiao, Junhua; Chemical communications (Cambridge, England) 60 (2024) 1924–1927; doi:10.1039/d3cc05436e

data_7132614
_publ_section_title
;
 CAMDOL-enabled diastereoselective synthesis of &#x3b1;-substituted
 phosphonates.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1924
_journal_page_last               1927
_journal_paper_doi               10.1039/d3cc05436e
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H33 O3 P'
_chemical_formula_sum            'C30 H33 O3 P'
_chemical_formula_weight         472.53
_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             2021-12-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-08-05 deposited with the CCDC.	2024-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.0231(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.97433(16)
_cell_length_b                   9.78846(14)
_cell_length_c                   11.7517(2)
_cell_measurement_reflns_used    6463
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      73.2780
_cell_measurement_theta_min      3.8050
_cell_volume                     1234.70(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_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     56.00 117.00   1.00    1.00    --   40.73  77.00 120.00   61
  2  \w    128.00 177.00   1.00    1.00    --  106.95 125.00   0.00   49
  3  \w     96.00 134.00   1.00    1.00    --  106.95 125.00  60.00   38
  4  \w     78.00 178.00   1.00    1.00    --  106.95  61.00 120.00  100
  5  \w    102.00 128.00   1.00    1.00    --  106.95 -30.00 -30.00   26
  6  \w     83.00 170.00   1.00    1.00    --  106.95  30.00-120.00   87
  7  \w     66.00  92.00   1.00    1.00    --  106.95 -30.00 -30.00   26
  8  \w     43.00 129.00   1.00    1.00    --  106.95 -61.00 -30.00   86
  9  \w     27.00  92.00   1.00    1.00    --   40.73-125.00 -90.00   65
 10  \w      2.00  54.00   1.00    1.00    --   40.73 -99.00   0.00   52
 11  \w    -49.00  -4.00   1.00    1.00    --  -40.73 125.00  30.00   45
 12  \w    -93.00 -36.00   1.00    1.00    --  -40.98 -38.00-120.00   57
 13  \w   -111.00 -52.00   1.00    1.00    --  -40.98 -57.00-150.00   59
 14  \w      8.00  65.00   1.00    1.00    --   40.98 -99.00  90.00   57
 15  \w     27.00  54.00   1.00    1.00    --   40.98-125.00 -60.00   27
 16  \w     75.00 155.00   1.00    1.00    --  106.95  77.00 -90.00   80
 17  \w     79.00 123.00   1.00    1.00    --  106.95  61.00  90.00   44
 18  \w     89.00 129.00   1.00    1.00    --  106.95  45.00-180.00   40
 19  \w     95.00 121.00   1.00    1.00    --  106.95-125.00 -90.00   26
 20  \w     78.00 103.00   1.00    1.00    --  106.95  61.00-120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0764282000
_diffrn_orient_matrix_UB_12      0.0350514000
_diffrn_orient_matrix_UB_13      -0.1219193000
_diffrn_orient_matrix_UB_21      0.0962170000
_diffrn_orient_matrix_UB_22      0.1102424000
_diffrn_orient_matrix_UB_23      -0.0136259000
_diffrn_orient_matrix_UB_31      0.0742286000
_diffrn_orient_matrix_UB_32      -0.1066745000
_diffrn_orient_matrix_UB_33      -0.0539564000
_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  0.0209
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7634
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.480
_diffrn_reflns_theta_min         3.846
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.217
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1866 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4546
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0451P)^2^+0.1162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.893
_reflns_Friedel_fraction_max     0.835
_reflns_number_gt                4460
_reflns_number_total             4546
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05436e2.cif
_cod_data_source_block           8195
_cod_depositor_comments          'Adding full bibliography for 7132614.cif.'
_cod_original_cell_volume        1234.69(3)
_cod_database_code               7132614
_shelx_shelxl_version_number     2018/3
_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:
 C12(H12), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C24(H24A,H24B,
 H24C)
;
_shelx_res_checksum              19581
_shelx_hkl_checksum              59009
_olex2_date_sample_data_collection 2021-12-18
_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 1.380
_oxdiff_exptl_absorpt_empirical_full_min 0.684