Controlling chirality in the synthesis of 4 + 4 diastereomeric amine macrocycles derived from <i>trans</i>-1,2-diaminocyclopentane and 2,6-diformylpyridine.
Fedorowicz, Dominika; Banach, Sylwia; Koza, Patrycja; Frydrych, Rafał; Ślepokura, Katarzyna; Gregoliński, Janusz; Organic & biomolecular chemistry 20 (2022) 1080–1094; doi:10.1039/d1ob02410h

data_7158468
_publ_section_title
;
 Controlling chirality in the synthesis of 4 + 4 diastereomeric amine
 macrocycles derived from <i>trans</i>-1,2-diaminocyclopentane and
 2,6-diformylpyridine.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1080
_journal_page_last               1094
_journal_paper_doi               10.1039/d1ob02410h
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C48 H76 N12, 8(Cl), 9(H2 O)'
_chemical_formula_sum            'C48 H94 Cl8 N12 O9'
_chemical_formula_weight         1266.95
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-07-22 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                75.36(2)
_cell_angle_beta                 79.83(2)
_cell_angle_gamma                89.70(2)
_cell_formula_units_Z            2
_cell_length_a                   12.441(2)
_cell_length_b                   12.772(2)
_cell_length_c                   20.693(4)
_cell_measurement_reflns_used    60334
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.21
_cell_measurement_theta_min      1.66
_cell_volume                     3128.6(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            126831
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         1.793
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.80a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       column
_exptl_crystal_F_000             1348
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 9363 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1472
_refine_ls_number_reflns         24381
_refine_ls_number_restraints     151
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1008P)^2^+2.3143P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1547
_refine_ls_wR_factor_ref         0.1597
_reflns_Friedel_coverage         0.976
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                21727
_reflns_number_total             24381
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02410h2.cif
_cod_data_source_block           4_l14rhc-mo
_cod_depositor_comments
'Adding full bibliography for 7158467--7158470.cif.'
_cod_database_code               7158468
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.921
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              52032