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_4035663
_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         'C6 H11 F N, Cl'
_chemical_formula_sum            'C6 H11 Cl F N'
_chemical_formula_weight         151.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 108.882(13)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.502(4)
_cell_length_b                   10.636(3)
_cell_length_c                   12.083(5)
_cell_measurement_reflns_used    552
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.87
_cell_measurement_theta_min      3.84
_cell_volume                     1520.2(9)
_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(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_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  0.0520
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.763
_diffrn_reflns_theta_min         1.722
_exptl_absorpt_coefficient_mu    0.434
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0367P)^2^+0.5294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2158
_reflns_number_total             3199
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02071_si_001.cif
_cod_data_source_block           xray78
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035663
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.835
_shelx_estimated_absorpt_t_max   0.926
_shelx_res_checksum              34509
_shelx_hkl_checksum              55753