Rapid, room-temperature self-organization of polyarylated 1<i>H</i>-pyrroles from acetylenes and nitriles in the KOBu<sup><i>t</i></sup>/DMSO system.
Schmidt, Elena Yu; Tatarinova, Inna V.; Lobanova, Natal'ya A.; Ushakov, Igor A.; Bagryanskaya, Irina Yu; Trofimov, Boris A.; Organic & biomolecular chemistry 21 (2023) 7209–7218; doi:10.1039/d3ob01311a

data_7159538
_publ_section_title
;
 Rapid, room-temperature self-organization of polyarylated
 1<i>H</i>-pyrroles from acetylenes and nitriles in the
 KOBu<sup><i>t</i></sup>/DMSO system.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7209
_journal_page_last               7218
_journal_paper_doi               10.1039/d3ob01311a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C29 H21 N S'
_chemical_formula_sum            'C29 H21 N S'
_chemical_formula_weight         415.53
_chemical_melting_point          430
_chemical_name_systematic
;
 2-Benzyl-3-phenyl-4-(phenylethynyl)-5-(thiophen-2-yl)-1H-pyrrole
;
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-05-05 deposited with the CCDC.	2023-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.507(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1310(4)
_cell_length_b                   8.5709(3)
_cell_length_c                   13.8389(5)
_cell_measurement_reflns_used    7702
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.06
_cell_measurement_theta_min      2.23
_cell_volume                     1082.67(7)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18631
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.231
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1716 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4956
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0330P)^2^+0.0877P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0756
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4183
_reflns_number_total             4956
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01311a2.cif
_cod_data_source_block           irk845
_cod_depositor_comments          'Adding full bibliography for 7159538.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159538
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.865
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              25799