Photochemical In-Flow Synthesis of 2,4-Methanopyrrolidines: Pyrrolidine Analogues with Improved Water Solubility and Reduced Lipophilicity.
Levterov, Vadym V.; Michurin, Oleg; Borysko, Petro O.; Zozulya, Sergey; Sadkova, Iryna V.; Tolmachev, Andrey A.; Mykhailiuk, Pavel K.; The Journal of organic chemistry 83 (2018) 14350–14361; doi:10.1021/acs.joc.8b02071

data_4035666
_publ_section_title
;
 Photochemical In-Flow Synthesis of 2,4-Methanopyrrolidines: Pyrrolidine
 Analogues with Improved Water Solubility and Reduced Lipophilicity.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14350
_journal_page_last               14361
_journal_paper_doi               10.1021/acs.joc.8b02071
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C8 H14 N O2, Cl'
_chemical_formula_sum            'C8 H14 Cl N O2'
_chemical_formula_weight         191.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 93.433(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0902(18)
_cell_length_b                   6.5152(17)
_cell_length_c                   24.172(7)
_cell_measurement_reflns_used    687
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.79
_cell_measurement_theta_min      3.24
_cell_volume                     957.4(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      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0854
_diffrn_reflns_av_unetI/netI     0.0934
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5959
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         1.688
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0762
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+0.3911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1545
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1095
_reflns_number_total             1711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02071_si_004.cif
_cod_data_source_block           xray80
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4035666
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.855
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              21356
_shelx_hkl_checksum              53773