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_1574060
_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         'C14 H17 O7 P'
_chemical_formula_sum            'C14 H17 O7 P'
_chemical_formula_weight         328.24
_chemical_name_systematic
;
methyl 4-((2R,3R)-2-(dimethoxyphosphoryl)-3-methyl-4-oxooxetan-2-yl)benzoate

;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_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                92.9757(16)
_cell_angle_beta                 90.6187(17)
_cell_angle_gamma                101.8462(16)
_cell_formula_units_Z            2
_cell_length_a                   6.35385(12)
_cell_length_b                   7.76034(15)
_cell_length_c                   16.0686(3)
_cell_measurement_reflns_used    17245
_cell_measurement_temperature    173
_cell_measurement_theta_max      30.4360
_cell_measurement_theta_min      2.5440
_cell_volume                     774.20(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_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_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P200K'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.912
_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  89.00   0.50   10.00    --    0.00  -1.00-150.00  356
  2  \w   -108.00 -18.00   0.50   10.00    --  -18.30  -1.00-150.00  180
  3  \w   -108.00  71.00   0.50   10.00    --  -18.30  42.00   0.00  358
  4  \w   -108.00  71.00   0.50   10.00    --  -18.30  42.00-150.00  358
  5  \w   -108.00  71.00   0.50   10.00    --  -18.30  42.00-120.00  358
  6  \w   -108.00  71.00   0.50   10.00    --  -18.30  42.00 150.00  358
  7  \w   -108.00  71.00   0.50   10.00    --  -18.30  42.00  90.00  358
  8  \w   -108.00  71.00   0.50   10.00    --  -18.30  42.00 -90.00  358
  9  \w   -108.00  71.00   0.50   10.00    --  -18.30  42.00 -30.00  358
 10  \w   -108.00  71.00   0.50   10.00    --  -18.30  42.00 -30.00  358
 11  \w   -108.00  71.00   0.50   10.00    --  -18.30  42.00  60.00  358
 12  \w   -108.00  71.00   0.50   10.00    --  -18.30  42.00 -60.00  358
 13  \w   -108.00  71.00   0.50   10.00    --  -18.30  42.00  30.00  358
 14  \w   -108.00  71.00   0.50   10.00    --  -18.30  42.00 120.00  358
;
_diffrn_measurement_device       'AFC11: Quarter \c 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0049953000
_diffrn_orient_matrix_UB_12      -0.0004374000
_diffrn_orient_matrix_UB_13      0.0441056000
_diffrn_orient_matrix_UB_21      0.1001136000
_diffrn_orient_matrix_UB_22      -0.0267796000
_diffrn_orient_matrix_UB_23      -0.0022371000
_diffrn_orient_matrix_UB_31      0.0544867000
_diffrn_orient_matrix_UB_32      0.0896161000
_diffrn_orient_matrix_UB_33      0.0020990000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            43057
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.342
_diffrn_reflns_theta_min         2.539
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku FR-X'
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.53a (Rigaku Oxford Diffraction, 2022)
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    1.408
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/hexane'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 3584 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   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         8979
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0512P)^2^+0.0721P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0876
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.851
_reflns_number_gt                8109
_reflns_number_total             8979
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00322a2.cif
_cod_data_source_block           18
_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_cell_volume        774.21(3)
_cod_original_sg_symbol_H-M      P1
_cod_database_code               1574060
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.963
_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), C27(H27)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C29(H29), C30(H30), C32(H32), C33(H33)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C),
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C36(H36A,H36B,H36C), C37(H37A,H37B,
 H37C)
;
_shelx_res_checksum              48200