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_4035664
_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 H9 F3 N, Cl'
_chemical_formula_sum            'C6 H9 Cl F3 N'
_chemical_formula_weight         187.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_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                   14.266(2)
_cell_length_b                   7.0245(11)
_cell_length_c                   7.9744(13)
_cell_measurement_reflns_used    708
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.06
_cell_measurement_theta_min      2.86
_cell_volume                     799.1(2)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0330
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5596
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.342
_diffrn_reflns_theta_min         2.856
_exptl_absorpt_coefficient_mu    0.464
_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    1.559
_exptl_crystal_description       prizm
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 513 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.22(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1476
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0327P)^2^+0.0728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0648
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.853
_reflns_Friedel_fraction_max     0.807
_reflns_number_gt                1344
_reflns_number_total             1476
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02071_si_003.cif
_cod_data_source_block           xray81
_cod_database_code               4035664
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.858
_shelx_estimated_absorpt_t_max   0.929
_shelx_res_checksum              56010
_shelx_hkl_checksum              64539