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#$Date: 2023-06-05 06:34:38 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284171 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/15/7131596.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7131596
loop_
_publ_author_name
'Nayak, Mithilesh Kumar'
'Elvers, Benedict J.'
'Mandal, Debdeep'
'Das, Ayan'
'Ramakrishnan, Raghunathan'
'Mote, Kaustubh R.'
'Schulzke, Carola'
'Yildiz, Cem Burak'
'Jana, Anukul'
_publ_section_title
;
 Reduction of 2-H-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         'C40 H64 N2'
_chemical_formula_sum            'C40 H64 N2'
_chemical_formula_weight         572.93
_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                 115.474(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.980(2)
_cell_length_b                   9.5392(8)
_cell_length_c                   20.618(3)
_cell_measurement_reflns_used    4632
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.1240
_cell_measurement_theta_min      2.9070
_cell_volume                     3547.6(8)
_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, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1445
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25298
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.415
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85065
_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    1.073
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0084(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0598
_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/[σ²(Fo²)+(0.0793P)²+1.1511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1539
_refine_ls_wR_factor_ref         0.1703
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2139
_reflns_number_total             3124
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc00891f2.cif
_cod_data_source_block           AJ1598-1
_cod_depositor_comments
'Adding full bibliography for 7131595--7131596.cif.'
_cod_original_cell_volume        3547.5(8)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7131596
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.57763(8) 0.51794(15) 0.34497(7) 0.0391(4) Uani 1 1 d . . . . .
C1 C 0.50061(9) 0.49166(17) 0.28852(8) 0.0343(4) Uani 1 1 d . . . . .
H1 H 0.471830 0.574161 0.289495 0.041 Uiso 1 1 calc R U . . .
C2 C 0.47091(10) 0.36786(19) 0.31980(10) 0.0460(5) Uani 1 1 d . . . . .
C3 C 0.54150(11) 0.3063(2) 0.37887(11) 0.0557(6) Uani 1 1 d . . . . .
H3A H 0.530758 0.266371 0.416630 0.067 Uiso 1 1 calc R U . . .
H3B H 0.560914 0.232709 0.359294 0.067 Uiso 1 1 calc R U . . .
C4 C 0.59803(11) 0.4237(2) 0.40899(10) 0.0520(5) Uani 1 1 d . . . . .
C5 C 0.59625(14) 0.4961(3) 0.47501(11) 0.0697(7) Uani 1 1 d . . . . .
H5A H 0.627984 0.576867 0.487510 0.105 Uiso 1 1 calc R U . . .
H5B H 0.613213 0.431839 0.514700 0.105 Uiso 1 1 calc R U . . .
H5C H 0.546441 0.524670 0.463972 0.105 Uiso 1 1 calc R U . . .
C6 C 0.67614(13) 0.3636(3) 0.43475(13) 0.0778(7) Uani 1 1 d . . . . .
H6A H 0.681498 0.321324 0.394986 0.117 Uiso 1 1 calc R U . . .
H6B H 0.684176 0.294158 0.471054 0.117 Uiso 1 1 calc R U . . .
H6C H 0.711839 0.437536 0.454385 0.117 Uiso 1 1 calc R U . . .
C7 C 0.42056(12) 0.4245(2) 0.35335(12) 0.0612(6) Uani 1 1 d . . . . .
H7A H 0.444855 0.501088 0.384915 0.092 Uiso 1 1 calc R U . . .
H7B H 0.410887 0.351164 0.380072 0.092 Uiso 1 1 calc R U . . .
H7C H 0.374606 0.456398 0.315927 0.092 Uiso 1 1 calc R U . . .
C8 C 0.42392(12) 0.2550(2) 0.26717(13) 0.0623(6) Uani 1 1 d . . . . .
H8A H 0.382917 0.298291 0.228173 0.093 Uiso 1 1 calc R U . . .
H8B H 0.405598 0.190736 0.291582 0.093 Uiso 1 1 calc R U . . .
H8C H 0.453772 0.205118 0.248725 0.093 Uiso 1 1 calc R U . . .
C9 C 0.61086(10) 0.65681(19) 0.35724(9) 0.0434(5) Uani 1 1 d . . . . .
C10 C 0.67976(11) 0.6769(2) 0.35394(11) 0.0593(6) Uani 1 1 d . . . . .
C11 C 0.71443(15) 0.8065(3) 0.37136(15) 0.0839(8) Uani 1 1 d . . . . .
H11 H 0.760614 0.817134 0.371167 0.101 Uiso 1 1 calc R U . . .
C12 C 0.68339(18) 0.9186(3) 0.38870(16) 0.0931(9) Uani 1 1 d . . . . .
H12 H 0.707619 1.004599 0.399745 0.112 Uiso 1 1 calc R U . . .
C13 C 0.61640(16) 0.9024(2) 0.38959(13) 0.0748(7) Uani 1 1 d . . . . .
H13 H 0.594531 0.979862 0.400088 0.090 Uiso 1 1 calc R U . . .
C14 C 0.57873(12) 0.7743(2) 0.37538(10) 0.0506(5) Uani 1 1 d . . . . .
C15 C 0.50484(12) 0.7750(2) 0.37907(10) 0.0540(5) Uani 1 1 d . . . . .
H15 H 0.486915 0.678088 0.373641 0.065 Uiso 1 1 calc R U . . .
C16 C 0.50982(17) 0.8312(3) 0.45112(14) 0.0847(8) Uani 1 1 d . . . . .
H16A H 0.547111 0.780119 0.490005 0.127 Uiso 1 1 calc R U . . .
H16B H 0.462789 0.819660 0.452653 0.127 Uiso 1 1 calc R U . . .
H16C H 0.522656 0.928852 0.455558 0.127 Uiso 1 1 calc R U . . .
C17 C 0.44807(15) 0.8608(3) 0.31784(14) 0.0776(7) Uani 1 1 d . . . . .
H17A H 0.464738 0.956139 0.321626 0.116 Uiso 1 1 calc R U . . .
H17B H 0.401317 0.858063 0.320567 0.116 Uiso 1 1 calc R U . . .
H17C H 0.442370 0.822337 0.272730 0.116 Uiso 1 1 calc R U . . .
C18 C 0.71910(12) 0.5682(3) 0.32923(14) 0.0727(7) Uani 1 1 d . . . . .
H18 H 0.688910 0.482781 0.315801 0.087 Uiso 1 1 calc R U . . .
C19 C 0.72833(16) 0.6215(4) 0.26318(16) 0.1003(10) Uani 1 1 d . . . . .
H19A H 0.680631 0.645239 0.225786 0.150 Uiso 1 1 calc R U . . .
H19B H 0.750631 0.549600 0.246409 0.150 Uiso 1 1 calc R U . . .
H19C H 0.759494 0.703131 0.276090 0.150 Uiso 1 1 calc R U . . .
C20 C 0.79714(14) 0.5306(4) 0.38782(19) 0.1175(12) Uani 1 1 d . . . . .
H20A H 0.831295 0.604143 0.391220 0.176 Uiso 1 1 calc R U . . .
H20B H 0.813457 0.444343 0.375332 0.176 Uiso 1 1 calc R U . . .
H20C H 0.795052 0.519992 0.433212 0.176 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C1 121.80(13) . . ?
C9 N1 C4 117.48(14) . . ?
C1 N1 C4 112.49(13) . . ?
N1 C1 C1 110.37(15) . 2_655 ?
N1 C1 C2 104.41(13) . . ?
C1 C1 C2 124.43(11) 2_655 . ?
N1 C1 H1 105.4 . . ?
C1 C1 H1 105.4 2_655 . ?
C2 C1 H1 105.4 . . ?
C3 C2 C8 111.64(17) . . ?
C3 C2 C7 109.46(16) . . ?
C8 C2 C7 104.17(17) . . ?
C3 C2 C1 103.45(14) . . ?
C8 C2 C1 117.42(16) . . ?
C7 C2 C1 110.70(15) . . ?
C4 C3 C2 108.11(15) . . ?
C4 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
N1 C4 C3 102.06(14) . . ?
N1 C4 C6 112.39(16) . . ?
C3 C4 C6 109.49(18) . . ?
N1 C4 C5 114.09(16) . . ?
C3 C4 C5 113.30(17) . . ?
C6 C4 C5 105.64(18) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 117.63(17) . . ?
C14 C9 N1 122.73(16) . . ?
C10 C9 N1 119.60(16) . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 C18 115.1(2) . . ?
C9 C10 C18 125.26(18) . . ?
C12 C11 C10 122.4(2) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C13 C12 C11 118.6(2) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 122.8(2) . . ?
C12 C13 H13 118.6 . . ?
C14 C13 H13 118.6 . . ?
C13 C14 C9 118.8(2) . . ?
C13 C14 C15 115.79(19) . . ?
C9 C14 C15 125.40(17) . . ?
C14 C15 C17 110.86(18) . . ?
C14 C15 C16 112.99(18) . . ?
C17 C15 C16 109.15(18) . . ?
C14 C15 H15 107.9 . . ?
C17 C15 H15 107.9 . . ?
C16 C15 H15 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 C19 110.4(2) . . ?
C10 C18 C20 112.9(2) . . ?
C19 C18 C20 107.7(2) . . ?
C10 C18 H18 108.6 . . ?
C19 C18 H18 108.6 . . ?
C20 C18 H18 108.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.454(2) . ?
N1 C1 1.498(2) . ?
N1 C4 1.501(2) . ?
C1 C1 1.578(3) 2_655 ?
C1 C2 1.579(2) . ?
C1 H1 0.9800 . ?
C2 C3 1.530(3) . ?
C2 C8 1.530(3) . ?
C2 C7 1.543(3) . ?
C3 C4 1.521(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C6 1.528(3) . ?
C4 C5 1.540(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C14 1.419(3) . ?
C9 C10 1.420(3) . ?
C10 C11 1.387(3) . ?
C10 C18 1.516(3) . ?
C11 C12 1.358(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.355(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.399(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.511(3) . ?
C15 C17 1.523(3) . ?
C15 C16 1.542(3) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.538(4) . ?
C18 C20 1.549(4) . ?
C18 H18 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
