Synthesis of imidazole-fused pentacyclic pyrrolo[3,4-c]coumarins via base-promoted rearrangement of coumarin-substituted N-heterocyclic carbene precursors
Karataş, Mert Olgun; Özdemir, Namık; Küçükbay, Hasan; New Journal of Chemistry 48 (2024) 16676–16682; doi:10.1039/D4NJ03146F

data_7063428
_publ_section_title
;
 Synthesis of imidazole-fused pentacyclic pyrrolo[3,4-c]coumarins via
 base-promoted rearrangement of coumarin-substituted N-heterocyclic
 carbene precursors
;
_journal_issue                   38
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16676
_journal_page_last               16682
_journal_paper_doi               10.1039/D4NJ03146F
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C23 H22 N2 O2'
_chemical_formula_sum            'C23 H22 N2 O2'
_chemical_formula_weight         358.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2023-12-17 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.9870(9)
_cell_length_b                   17.1569(16)
_cell_length_c                   24.1034(18)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      1.69
_cell_volume                     3716.5(6)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    '0.8 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0830
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15712
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.050
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_min         1.690
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9610
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-RED32 (Stoe & Cie, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       prism
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.900
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0493P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1210
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1591
_reflns_number_total             3294
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj03146f2.cif
_cod_data_source_block           2a
_cod_depositor_comments
'Adding full bibliography for 7063428--7063431.cif.'
_cod_database_code               7063428
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              83948