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_4038826
_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         'C42 H30 F12 N2'
_chemical_formula_sum            'C42 H30 F12 N2'
_chemical_formula_weight         790.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 97.551(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0701(1)
_cell_length_b                   25.7968(6)
_cell_length_c                   10.8547(3)
_cell_measurement_reflns_used    6444
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      69.9400
_cell_measurement_theta_min      3.4240
_cell_volume                     1684.99(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector_area_resol_mean 16.2974
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17251
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.998
_diffrn_reflns_theta_min         7.559
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_description       needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0537P)^2^+0.5685P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2728
_reflns_number_total             3194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01665_si_002.cif
_cod_data_source_block           ov_892
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038826
_shelx_estimated_absorpt_t_min   0.679
_shelx_estimated_absorpt_t_max   0.942
_shelxl_version_number           2013-3
_shelx_res_checksum              47684
_shelx_hkl_checksum              81144