Design and process study of chiral separation of (2S,4S)-1-(tert-butoxy carbonyl)-4-(methoxymethyl) pyrrolidine-2-carboxylic acid for green manufacturing
Ge, Shuwang; Fu, Mingwei; Gu, Dihai; Wei, Lai; Qian, Kun; Rui, Qi; Ma, Yan; Li, Liang; Wang, Huaiqiu; Li, Lingchao; Ge, Min; Wang, Yihong; Green Chemistry 26 (2024) 2673–2683; doi:10.1039/D3GC04435A

data_7248017
_publ_section_title
;
 Design and process study of chiral separation of (2S,4S)-1-(tert-butoxy
 carbonyl)-4-(methoxymethyl) pyrrolidine-2-carboxylic acid for green
 manufacturing
;
_journal_issue                   5
_journal_name_full               'Green Chemistry'
_journal_page_first              2673
_journal_page_last               2683
_journal_paper_doi               10.1039/D3GC04435A
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C12 H21 N O5, H2 O'
_chemical_formula_sum            'C12 H23 N O6'
_chemical_formula_weight         277.31
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-06-26 deposited with the CCDC.	2024-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                71.6660(10)
_cell_angle_beta                 86.2690(10)
_cell_angle_gamma                86.1690(10)
_cell_formula_units_Z            1
_cell_length_a                   5.8953(2)
_cell_length_b                   7.8109(2)
_cell_length_c                   8.5294(2)
_cell_measurement_reflns_used    7688
_cell_measurement_temperature    170
_cell_measurement_theta_max      79.974
_cell_measurement_theta_min      9.539
_cell_volume                     371.586(18)
_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      170.0
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_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       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7140
_diffrn_reflns_point_group_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        66.577
_diffrn_reflns_theta_max         66.577
_diffrn_reflns_theta_min         9.539
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0935 before and 0.0512 after correction. The Ratio of minimum to maximum transmission is 0.9223. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       needle
_exptl_crystal_F_000             150
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.107
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 1084 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0243
_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^)+(0.0243P)^2^+0.0464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0619
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.841
_reflns_Friedel_fraction_max     0.841
_reflns_number_gt                2355
_reflns_number_total             2362
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc04435a3.cif
_cod_data_source_block           GSW_TBMP_Monohydrate
_cod_depositor_comments
'Adding full bibliography for 7248016--7248017.cif.'
_cod_database_code               7248017
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.907
_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, All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
2.c Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C2(H2A,H2B), C5(H5A,H5B)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C6(H6A,H6B,H6C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'