Scalable Synthesis of Biologically Relevant Spirocyclic Pyrrolidines.
Melnykov, Kostiantyn P.; Artemenko, Artem N.; Ivanenko, Bohdan O.; Sokolenko, Yevhenii M.; Nosik, Pavel S.; Ostapchuk, Eugeniy N.; Grygorenko, Oleksandr O.; Volochnyuk, Dmitriy M.; Ryabukhin, Sergey V.; ACS omega 4 (2019) 7498–7515; doi:10.1021/acsomega.9b00896

data_4515043
_publ_section_title
;
 Scalable Synthesis of Biologically Relevant Spirocyclic Pyrrolidines.
;
_journal_issue                   4
_journal_name_full               'ACS omega'
_journal_page_first              7498
_journal_page_last               7515
_journal_paper_doi               10.1021/acsomega.9b00896
_journal_volume                  4
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C8 H15 N O2 S, Cl'
_chemical_formula_sum            'C8 H15 Cl N O2 S'
_chemical_formula_weight         224.72
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2398(18)
_cell_length_b                   8.637(2)
_cell_length_c                   16.178(5)
_cell_measurement_reflns_used    463
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      22.86
_cell_measurement_theta_min      2.52
_cell_volume                     1011.6(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11327
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.977
_diffrn_reflns_theta_min         2.518
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       prizm
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 640 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+0.1624P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0840
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1737
_reflns_number_total             1980
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao9b00896_si_002.cif
_cod_data_source_block           xr133
_cod_database_code               4515043
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.874
_shelx_estimated_absorpt_t_max   0.937
_shelx_res_checksum              66840
_shelx_hkl_checksum              49951