Two-Step Macrocycle Synthesis by Classical Ugi Reaction.
Abdelraheem, Eman M. M.; Khaksar, Samad; Kurpiewska, Katarzyna; Kalinowska-Tłuścik, Justyna; Shaabani, Shabnam; Dömling, Alexander; The Journal of organic chemistry 83 (2018) 1441–1447; doi:10.1021/acs.joc.7b02984

data_4033428
_publ_section_title
;
 Two-Step Macrocycle Synthesis by Classical Ugi Reaction.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1441
_journal_page_last               1447
_journal_paper_doi               10.1021/acs.joc.7b02984
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C22 H33 N3 O3 S'
_chemical_formula_sum            'C22 H33 N3 O3 S'
_chemical_formula_weight         419.57
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-10-03T21:48:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                63.848(4)
_cell_angle_beta                 75.238(5)
_cell_angle_gamma                85.703(4)
_cell_formula_units_Z            2
_cell_length_a                   10.2751(6)
_cell_length_b                   10.9293(5)
_cell_length_c                   11.4868(5)
_cell_measurement_reflns_used    9471
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      28.588
_cell_measurement_theta_min      3.675
_cell_volume                     1118.65(11)
_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-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0677621
_diffrn_orient_matrix_UB_12      -0.0028391
_diffrn_orient_matrix_UB_13      -0.0332106
_diffrn_orient_matrix_UB_21      0.0125468
_diffrn_orient_matrix_UB_22      0.0683983
_diffrn_orient_matrix_UB_23      -0.0131781
_diffrn_orient_matrix_UB_31      0.0188824
_diffrn_orient_matrix_UB_32      -0.0234668
_diffrn_orient_matrix_UB_33      0.0613612
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15096
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.671
_diffrn_reflns_theta_min         3.232
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8978
_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            white
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       prism
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.448
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.15
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5163
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.1178
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1226P)^2^+14.2611P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3688
_refine_ls_wR_factor_ref         0.3714
_reflns_Friedel_coverage         0
_reflns_number_gt                4659
_reflns_number_total             5163
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02984_si_002.cif
_cod_data_source_block           ea649a_1
_cod_depositor_comments
'Adding full bibliography for 4033426--4033428.cif.'
_cod_database_code               4033428
_shelx_estimated_absorpt_t_min   0.95
_shelx_estimated_absorpt_t_max   0.983