Reduction of 2-<i>H</i>-substituted pyrrolinium cations: the carbon-carbon single bond in air stable 2,2'-bipyrrolidines as a two-electron-source.
Nayak, Mithilesh Kumar; Elvers, Benedict J.; Mandal, Debdeep; Das, Ayan; Ramakrishnan, Raghunathan; Mote, Kaustubh R.; Schulzke, Carola; Yildiz, Cem Burak; Jana, Anukul; Chemical communications (Cambridge, England) 59 (2023) 6698–6701; doi:10.1039/d3cc00891f

data_7131595
_publ_section_title
;
 Reduction of 2-<i>H</i>-substituted pyrrolinium cations: the
 carbon-carbon single bond in air stable 2,2'-bipyrrolidines as a
 two-electron-source.
;
_journal_issue                   44
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6698
_journal_page_last               6701
_journal_paper_doi               10.1039/d3cc00891f
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C24 H48 N2'
_chemical_formula_sum            'C24 H48 N2'
_chemical_formula_weight         364.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-01-15 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.727(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.4911(16)
_cell_length_b                   8.0630(7)
_cell_length_c                   15.8001(11)
_cell_measurement_reflns_used    2926
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.0430
_cell_measurement_theta_min      3.0790
_cell_volume                     2339.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2376
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.993
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.059
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.035
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0755
_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^)+(0.0554P)^2^+3.0596P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1825
_refine_ls_wR_factor_ref         0.1996
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1530
_reflns_number_total             2376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00891f2.cif
_cod_data_source_block           AJ1609_tw
_cod_depositor_comments
'Adding full bibliography for 7131595--7131596.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7131595
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              39298
_shelx_hkl_checksum              61598