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_4034318
_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
'C75 H120 N18, 12(Cl), 2(C2 H3 N), 3.5(C H4 O), 6.5(H2 O)'
_chemical_formula_sum            'C82.5 H153 Cl12 N20 O10'
_chemical_formula_weight         2010.64
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                97.64(4)
_cell_angle_beta                 117.19(5)
_cell_angle_gamma                91.85(3)
_cell_formula_units_Z            1
_cell_length_a                   14.186(5)
_cell_length_b                   15.161(5)
_cell_length_c                   15.444(6)
_cell_measurement_reflns_used    5493
_cell_measurement_temperature    80(2)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      2.72
_cell_volume                     2912(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      80(2)
_diffrn_detector_area_resol_mean 10.3456
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type
'Agilent Technologies Xcalibur R kappa-geometry diffractometer with a Ruby CCD camera'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17447
_diffrn_reflns_point_group_measured_fraction_full 0.578
_diffrn_reflns_point_group_measured_fraction_max 0.569
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.726
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.873
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details
;
 Flack x determined using 1509 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1145
_refine_ls_number_reflns         13022
_refine_ls_number_restraints     226
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0881
_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^)+(0.1935P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2522
_refine_ls_wR_factor_ref         0.2747
_reflns_Friedel_coverage         0.172
_reflns_Friedel_fraction_full    0.178
_reflns_Friedel_fraction_max     0.167
_reflns_number_gt                10330
_reflns_number_total             13022
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00614_si_001.cif
_cod_data_source_block           3B_mhga
_cod_original_formula_sum        'C82.50 H153 Cl12 N20 O10'
_cod_database_code               4034318
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.865
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              36504
_shelx_hkl_checksum              52064