Synthesis and application of chiral <i>cis</i>-2,5-disubstituted pyrrolidine organocatalysts.
Singh, Suraj; Kumar, Rohtash; Dubey, Navneet Nandgopal; Appayee, Chandrakumar; Chemical communications (Cambridge, England) 60 (2024) 8768–8771; doi:10.1039/d4cc03132f

data_7133382
_publ_section_title
;
 Synthesis and application of chiral <i>cis</i>-2,5-disubstituted
 pyrrolidine organocatalysts.
;
_journal_issue                   66
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8768
_journal_page_last               8771
_journal_paper_doi               10.1039/d4cc03132f
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration S
_chemical_formula_moiety         'C27 H31 N O4 S'
_chemical_formula_sum            'C27 H31 N O4 S'
_chemical_formula_weight         465.59
_chemical_melting_point          349.5(15)
_chemical_name_common            dihydroxy_tosylate
_chemical_name_systematic
3-((2R,5S)-5-(hydroxydiphenylmethyl)-1-tosylpyrrolidin-2-yl)propan-1-ol
_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_method           SHELXL-2018/3
_audit_update_record
;
2023-11-23 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2369(3)
_cell_length_b                   10.0180(5)
_cell_length_c                   39.109(2)
_cell_measurement_reflns_used    9837
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.50
_cell_measurement_theta_min      2.28
_cell_volume                     2443.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            54504
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        22.593
_diffrn_reflns_theta_max         22.593
_diffrn_reflns_theta_min         2.083
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   1
_exptl_transmission_factor_min   0
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1207 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.289
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.289
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0462
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1435
_refine_ls_wR_factor_ref         0.1453
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3105
_reflns_number_total             3228
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03132f2.cif
_cod_data_source_block           ACK_DiOl_NTs_NEW_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '348-351k' was changed to
'349.5(15)' -- the average value was taken and precision was
estimated.

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' 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 7133382--7133383.cif.
;
_cod_database_code               7133382
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              34372
_shelx_hkl_checksum              87446