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_7063430
_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         'C22 H20 N2 O3'
_chemical_formula_sum            'C22 H20 N2 O3'
_chemical_formula_weight         360.40
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_space_group_name_Hall           '-P 1'
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_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                103.148(16)
_cell_angle_beta                 100.212(16)
_cell_angle_gamma                100.313(16)
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_cell_length_b                   9.5451(18)
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_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.37
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_cell_volume                     893.7(3)
_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)'
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'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)
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_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  0.0958
_diffrn_reflns_av_unetI/netI     0.1114
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
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_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9482
_diffrn_reflns_point_group_measured_fraction_full 1.000
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_diffrn_reflns_theta_full        25.049
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_min         1.730
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
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_exptl_absorpt_correction_T_min  0.9751
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_exptl_absorpt_process_details   'X-RED32 (Stoe & Cie, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
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_refine_diff_density_min         -0.142
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_refine_ls_extinction_coef       0.0103(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.882
_refine_ls_R_factor_all          0.1585
_refine_ls_R_factor_gt           0.0516
_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^)+(0.0172P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0864
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1346
_reflns_number_total             3167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj03146f2.cif
_cod_data_source_block           2j
_cod_depositor_comments
'Adding full bibliography for 7063428--7063431.cif.'
_cod_database_code               7063430
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              59303