Mixed Macrocycles Derived from 2,6-Diformylpyridine and Opposite Enantiomers of trans-1,2-Diaminocyclopentane and trans-1,2-Diaminocyclohexane.
Frydrych, Rafał; Ślepokura, Katarzyna; Bil, Andrzej; Gregoliński, Janusz; The Journal of organic chemistry 84 (2019) 5695–5711; doi:10.1021/acs.joc.9b00614

data_4034317
_publ_section_title
;
 Mixed Macrocycles Derived from 2,6-Diformylpyridine and Opposite
 Enantiomers of trans-1,2-Diaminocyclopentane and
 trans-1,2-Diaminocyclohexane.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5695
_journal_page_last               5711
_journal_paper_doi               10.1021/acs.joc.9b00614
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C50 H80 N12, 8(Cl), 5(H2 O)'
_chemical_formula_sum            'C50 H90 Cl8 N12 O5'
_chemical_formula_weight         1222.93
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                77.96(2)
_cell_angle_beta                 82.87(2)
_cell_angle_gamma                64.67(3)
_cell_formula_units_Z            2
_cell_length_a                   12.549(3)
_cell_length_b                   13.394(3)
_cell_length_c                   20.848(5)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.63
_cell_measurement_theta_min      3.05
_cell_volume                     3095.2(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_detector_type            'Sapphire2, large Be window'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Kuma KM-4 CCD, kappa-geometry diffractometer with a Sapphire2 CCD camera'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23275
_diffrn_reflns_point_group_measured_fraction_full 0.636
_diffrn_reflns_point_group_measured_fraction_max 0.568
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.664
_diffrn_reflns_theta_min         3.000
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.417
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       plate
_exptl_crystal_F_000             1300
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1389
_refine_ls_number_reflns         18088
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0668
_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^)+(0.1126P)^2^+1.3611P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1714
_refine_ls_wR_factor_ref         0.1904
_reflns_Friedel_coverage         0.269
_reflns_Friedel_fraction_full    0.291
_reflns_Friedel_fraction_max     0.241
_reflns_number_gt                14984
_reflns_number_total             18088
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00614_si_001.cif
_cod_data_source_block           2B_mh42c
_cod_database_code               4034317
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.828
_shelx_estimated_absorpt_t_max   0.975
_shelx_res_checksum              14315
_shelx_hkl_checksum              21652