Parallel kinetic resolution of aziridines <i>via</i> chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening.
Liu, Juan; Du, Yi-Ying; He, Yu-Shi; Liang, Yan; Liu, Shang-Zhong; Li, Yi-Yi; Cao, Yi-Ming; Chemical science 14 (2023) 12152–12159; doi:10.1039/d3sc03899h

data_1570101
_publ_section_title
;
 Parallel kinetic resolution of aziridines <i>via</i> chiral phosphoric
 acid-catalyzed apparent hydrolytic ring-opening.
;
_journal_issue                   43
_journal_name_full               'Chemical science'
_journal_page_first              12152
_journal_page_last               12159
_journal_paper_doi               10.1039/d3sc03899h
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H19 N O4 S'
_chemical_formula_sum            'C16 H19 N O4 S'
_chemical_formula_weight         321.38
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-02-24 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.54870(10)
_cell_length_b                   11.1741(2)
_cell_length_c                   18.1225(3)
_cell_measurement_reflns_used    8900
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.457
_cell_measurement_theta_min      2.438
_cell_volume                     1528.63(4)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10288
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.450
_diffrn_reflns_theta_min         4.649
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.044
_exptl_absorpt_correction_T_max  0.1163
_exptl_absorpt_correction_T_min  0.0175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1143 before and 0.0713 after correction. The Ratio of minimum to maximum transmission is 0.1505. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1201 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3070
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0659P)^2^+0.0835P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                2991
_reflns_number_total             3070
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03899h2.cif
_cod_data_source_block           s_0m
_cod_depositor_comments          'Adding full bibliography for 1570101.cif.'
_cod_database_code               1570101
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.905
_shelx_estimated_absorpt_t_min   0.792
_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, All O(H) groups
2. Restrained distances
 N1-H1
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C10(H10), C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C15(H15), C16(H16), C12(H12), C4(H4A), C14(H14), C13(H13), C7(H7),
 C3(H3A)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
3.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'