Method for the Large-Scale Synthesis of Multifunctional 1,4-Dihydro-pyrrolo[3,2-<i>b</i>]pyrroles.
Tasior, Mariusz; Vakuliuk, Olena; Koga, Daiki; Koszarna, Beata; Górski, Krzysztof; Grzybowski, Marek; Kielesiński, Łukasz; Krzeszewski, Maciej; Gryko, Daniel T.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01665

data_4038825
_publ_section_title
;
 Method for the Large-Scale Synthesis of Multifunctional
 1,4-Dihydro-pyrrolo[3,2-<i>b</i>]pyrroles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01665
_journal_year                    2020
_chemical_formula_moiety         'C40 H28 N6 O2'
_chemical_formula_sum            'C40 H28 N6 O2'
_chemical_formula_weight         624.68
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                93.163(2)
_cell_angle_beta                 100.157(2)
_cell_angle_gamma                107.529(2)
_cell_formula_units_Z            2
_cell_length_a                   11.3043(4)
_cell_length_b                   11.6698(4)
_cell_length_c                   13.0106(4)
_cell_measurement_reflns_used    3658
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.59
_cell_measurement_theta_min      3.47
_cell_volume                     1600.24(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            45223
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_min         3.474
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  0.8980
_exptl_absorpt_correction_T_min  0.8300
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.168
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     501
_refine_ls_number_reflns         5522
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0903P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1477
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3658
_reflns_number_total             5522
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01665_si_003.cif
_cod_data_source_block           MT1257_0m
_cod_original_cell_volume        1600.24(9)
_cod_database_code               4038825
_shelx_estimated_absorpt_t_min   0.830
_shelx_estimated_absorpt_t_max   0.898
_shelxl_version_number           2014-3
_shelx_res_checksum              38971
_shelx_hkl_checksum              89136