Enantiopure Tertiary Urea and Thiourea Derivatives of Trianglamine Macrocycle: Structural Studies and Metallogeling Properties.
Prusinowska, Natalia; Szymkowiak, Joanna; Kwit, Marcin; The Journal of organic chemistry 83 (2018) 1167–1175; doi:10.1021/acs.joc.7b02600

data_4033389
_publ_section_title
;
 Enantiopure Tertiary Urea and Thiourea Derivatives of Trianglamine
 Macrocycle: Structural Studies and Metallogeling Properties.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1167
_journal_page_last               1175
_journal_paper_doi               10.1021/acs.joc.7b02600
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration R
_chemical_formula_moiety         'C45 H54 N6 S3, 1.5(C4 H8 O2)'
_chemical_formula_sum            'C51 H66 N6 O3 S3'
_chemical_formula_weight         907.27
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.949(11)
_cell_angle_gamma                90
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_cell_length_b                   13.6590(12)
_cell_length_c                   29.429(3)
_cell_measurement_reflns_used    13122
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      25.8280
_cell_measurement_theta_min      3.4150
_cell_volume                     5364.8(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics
'Mercury, Version 3.9 for Windows; ORTEP-3 for Windows'
_computing_structure_refinement
'SHELXL-2014/7 (Sheldrick, 2014), PLATON SQUEEZE (Spek, 2015)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 8.0169
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       '/w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_av_unetI/netI     0.0881
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            94981
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         4.089
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_description       prism
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 4516 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     973
_refine_ls_number_reflns         18854
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0961
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1066P)^2^+5.9019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2243
_refine_ls_wR_factor_ref         0.2389
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                14445
_reflns_number_total             18854
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02600_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 4033389.cif.'
_cod_database_code               4033389
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              22092
_shelx_hkl_checksum              83497