Isothiourea-catalysed enantioselective synthesis of phosphonate-functionalised β-lactones
Platt, Ffion M.; Wang, Yihong; Cordes, David B.; McKay, Aidan P.; Slawin, Alexandra M. Z.; Panchal, Heena; Smith, Andrew D.; Chemical Science 16 (2025) 6828–6836; doi:10.1039/D5SC00322A

data_1574061
_publ_section_title
;
 Isothiourea-catalysed enantioselective synthesis of
 phosphonate-functionalised \b-lactones
;
_journal_issue                   16
_journal_name_full               'Chemical Science'
_journal_page_first              6828
_journal_page_last               6836
_journal_paper_doi               10.1039/D5SC00322A
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H17 O5 P'
_chemical_formula_sum            'C16 H17 O5 P'
_chemical_formula_weight         320.26
_chemical_name_systematic
;
dimethyl ((2R,3R)-3-methyl-2-naphthalen-2-yl-4-oxooxetan-2-yl)phosphonate
;
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-12
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-14 deposited with the CCDC.	2025-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2790(2)
_cell_length_b                   8.1645(3)
_cell_length_c                   30.2310(10)
_cell_measurement_reflns_used    11547
_cell_measurement_temperature    173
_cell_measurement_theta_max      67.8940
_cell_measurement_theta_min      5.7940
_cell_volume                     1549.79(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_type            'Dectris PILATUS P100K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f      0.00 200.00   0.50    1.00   0.00 -30.00   0.00    --   400
  2  \w    -72.00   1.00   0.50    1.00    --  -30.00 -72.00 -90.00  146
  3  \w   -111.00 -69.00   0.50    1.00    --  -30.00 180.00 -45.00   84
  4  \f      0.00 200.00   0.50    1.00   0.00 -67.00   0.00    --   400
  5  \w    -83.00 -11.00   0.50    1.00    --  -67.00  72.00  90.00  144
  6  \w   -133.00 -93.00   0.50    1.00    --  -67.00 180.00   0.00   80
  7  \w    -83.00 -10.00   0.50    1.00    --  -67.00  72.00 -90.00  146
  8  \w   -126.00 -86.00   0.50    1.00    --  -67.00 180.00-180.00   80
  9  \f      0.00 200.00   0.50    1.00 -25.00-110.00   0.00    --   400
 10  \w   -126.00 -20.00   0.50    1.00    -- -110.00  72.00-135.00  212
 11  \w   -126.00 -20.00   0.50    1.00    -- -110.00  72.00  45.00  212
 12  \w   -115.00 -20.00   0.50    1.00    -- -110.00  72.00 -45.00  190
 13  \w   -113.00 -23.00   0.50    1.00    -- -110.00  72.00 135.00  180
 14  \w   -141.00 -46.00   0.50    1.00    -- -110.00 180.00 -90.00  190
 15  \w   -141.00 -46.00   0.50    1.00    -- -110.00 180.00-180.00  190
 16  \w   -141.00 -59.00   0.50    1.00    -- -110.00 180.00  90.00  164
 17  \w   -141.00 -55.00   0.50    1.00    -- -110.00 180.00   0.00  172
 18  \w   -141.00 -59.00   0.50    1.00    -- -110.00 180.00  45.00  164
 19  \w   -141.00 -78.00   0.50    1.00    -- -110.00 180.00 -45.00  126
 20  \w   -140.00 -77.00   0.50    1.00    -- -110.00 180.00-135.00  126
 21  \w   -140.00 -56.00   0.50    1.00    -- -110.00 180.00 135.00  168
;
_diffrn_measurement_device       'AFC12: Kappa 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P100K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2352868000
_diffrn_orient_matrix_UB_12      -0.0399899000
_diffrn_orient_matrix_UB_13      -0.0096502000
_diffrn_orient_matrix_UB_21      0.0394612000
_diffrn_orient_matrix_UB_22      0.1800077000
_diffrn_orient_matrix_UB_23      -0.0128342000
_diffrn_orient_matrix_UB_31      0.0575195000
_diffrn_orient_matrix_UB_32      0.0399688000
_diffrn_orient_matrix_UB_33      0.0483540000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0915
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16081
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.319
_diffrn_reflns_theta_min         2.923
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_exptl_absorpt_coefficient_mu    1.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
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    1.373
_exptl_crystal_description       rod
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/hexane'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 997 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0895P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1135
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2601
_reflns_number_total             2816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00322a2.cif
_cod_data_source_block           26
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1574060--1574062.cif.
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1574061
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.569
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              81666