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_4034316
_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
'C25 H40 N6, 4(Cl), 1.7(C2 H3 N), 1.2(C H4 O), 0.4(H2 O)'
_chemical_formula_sum            'C29.6 H50.7 Cl4 N7.7 O1.6'
_chemical_formula_weight         681.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.11(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.394(3)
_cell_length_b                   15.759(4)
_cell_length_c                   11.845(4)
_cell_measurement_reflns_used    5143
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      30.65
_cell_measurement_theta_min      3.00
_cell_volume                     1752.3(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      85(2)
_diffrn_detector_area_resol_mean 10.3456
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.893
_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  0.0179
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10317
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.780
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.721
_diffrn_reflns_theta_min         3.011
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             726
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 3018 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         8507
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0380P)^2^+0.3748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.883
_reflns_Friedel_fraction_max     0.658
_reflns_number_gt                7902
_reflns_number_total             8507
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00614_si_001.cif
_cod_data_source_block           1B_jgm4h
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C29.60 H50.70 Cl4 N7.70 O1.60'
_cod_database_code               4034316
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.823
_shelx_estimated_absorpt_t_max   0.861
_shelx_res_checksum              11847
_shelx_hkl_checksum              24179