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_4034314
_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 syn
_chemical_formula_moiety         'C50 H56 N12, C H2 Cl2'
_chemical_formula_sum            'C51 H58 Cl2 N12'
_chemical_formula_weight         909.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           3
_space_group_name_Hall           'P 2y'
_space_group_name_H-M_alt        'P 1 2 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                90
_cell_angle_beta                 91.35(3)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   14.606(4)
_cell_length_b                   5.425(2)
_cell_length_c                   15.600(4)
_cell_measurement_reflns_used    1150
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.83
_cell_measurement_theta_min      2.78
_cell_volume                     1235.8(7)
_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 8.1956
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur PX kappa-geometry diffractometer with an Onyx CCD camera'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.1061
_diffrn_reflns_av_unetI/netI     0.1177
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4624
_diffrn_reflns_point_group_measured_fraction_full 0.843
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         67.994
_diffrn_reflns_theta_min         2.833
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.552
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.687
_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    1.223
_exptl_crystal_description       plate
_exptl_crystal_F_000             482
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.35(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4624
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0746
_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^)+(0.0850P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1741
_refine_ls_wR_factor_ref         0.1934
_reflns_Friedel_coverage         0.513
_reflns_Friedel_fraction_full    0.645
_reflns_Friedel_fraction_max     0.645
_reflns_number_gt                2556
_reflns_number_total             4624
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00614_si_001.cif
_cod_data_source_block           2A_i42
_cod_original_sg_symbol_H-M      'P 2'
_cod_database_code               4034314
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.499
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              33079
_shelx_hkl_checksum              58691