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#$Date: 2024-10-06 12:07:36 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295321 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/34/7063430.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7063430
loop_
_publ_author_name
'Karataş, Mert Olgun'
'Özdemir, Namık'
'Küçükbay, Hasan'
_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
_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   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                103.148(16)
_cell_angle_beta                 100.212(16)
_cell_angle_gamma                100.313(16)
_cell_formula_units_Z            2
_cell_length_a                   8.0850(16)
_cell_length_b                   9.5451(18)
_cell_length_c                   12.413(3)
_cell_measurement_reflns_used    6596
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      1.73
_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)'
_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       'ω 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
_diffrn_reflns_limit_k_max       11
_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
_diffrn_reflns_point_group_measured_fraction_max 1.000
_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'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_type   integration
_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
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0103(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0172P)²] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4374(3) 1.0950(2) 0.73487(18) 0.0799(7) Uani 1 1 d . . . . .
O2 O 0.0641(3) 0.6104(2) 0.27871(18) 0.0629(6) Uani 1 1 d . . . . .
O3 O 0.0413(3) 0.8087(2) 0.40190(18) 0.0718(7) Uani 1 1 d . . . . .
N1 N 0.2071(3) 0.8030(3) 0.6784(2) 0.0551(7) Uani 1 1 d . . . . .
N2 N 0.2711(3) 0.5841(3) 0.6371(2) 0.0545(7) Uani 1 1 d . . . . .
C1 C 0.5760(5) 1.1891(4) 0.7141(3) 0.0912(12) Uani 1 1 d . . . . .
H1A H 0.609411 1.138810 0.647991 0.137 Uiso 1 1 calc R U . . .
H1B H 0.672025 1.216620 0.778440 0.137 Uiso 1 1 calc R U . . .
H1C H 0.541316 1.276261 0.701515 0.137 Uiso 1 1 calc R U . . .
C2 C 0.2955(4) 1.0446(3) 0.6421(3) 0.0666(9) Uani 1 1 d . . . . .
H2A H 0.330917 0.995676 0.575415 0.080 Uiso 1 1 calc R U . . .
H2B H 0.251951 1.127861 0.626318 0.080 Uiso 1 1 calc R U . . .
C3 C 0.1561(4) 0.9390(3) 0.6668(3) 0.0605(9) Uani 1 1 d . . . . .
H3A H 0.127037 0.986460 0.736525 0.073 Uiso 1 1 calc R U . . .
H3B H 0.053640 0.914776 0.605873 0.073 Uiso 1 1 calc R U . . .
C4 C 0.2749(4) 0.7736(4) 0.7799(3) 0.0585(9) Uani 1 1 d . . . . .
C5 C 0.3058(4) 0.8558(4) 0.8912(3) 0.0733(11) Uani 1 1 d . . . . .
H5 H 0.282791 0.949317 0.908911 0.088 Uiso 1 1 calc R U . . .
C6 C 0.3715(5) 0.7956(4) 0.9750(3) 0.0831(11) Uani 1 1 d . . . . .
H6 H 0.395249 0.849973 1.050514 0.100 Uiso 1 1 calc R U . . .
C7 C 0.4033(5) 0.6552(5) 0.9493(3) 0.0882(12) Uani 1 1 d . . . . .
H7 H 0.444193 0.616374 1.008329 0.106 Uiso 1 1 calc R U . . .
C8 C 0.3761(4) 0.5720(4) 0.8391(3) 0.0750(11) Uani 1 1 d . . . . .
H8 H 0.398573 0.478205 0.821764 0.090 Uiso 1 1 calc R U . . .
C9 C 0.3133(4) 0.6356(3) 0.7555(3) 0.0567(9) Uani 1 1 d . . . . .
C10 C 0.2805(4) 0.4663(3) 0.5510(3) 0.0554(9) Uani 1 1 d . . . . .
H10 H 0.321124 0.383658 0.560363 0.067 Uiso 1 1 calc R U . . .
C11 C 0.2189(4) 0.4942(3) 0.4493(3) 0.0505(8) Uani 1 1 d . . . . .
C12 C 0.1957(4) 0.4162(3) 0.3313(3) 0.0493(8) Uani 1 1 d . . . . .
C13 C 0.2439(4) 0.2825(3) 0.2894(3) 0.0595(9) Uani 1 1 d . . . . .
C14 C 0.3314(4) 0.2059(3) 0.3691(3) 0.0725(10) Uani 1 1 d . . . . .
H14A H 0.252891 0.171992 0.412371 0.109 Uiso 1 1 calc R U . . .
H14B H 0.431895 0.273934 0.419786 0.109 Uiso 1 1 calc R U . . .
H14C H 0.364944 0.123066 0.325959 0.109 Uiso 1 1 calc R U . . .
C15 C 0.2118(4) 0.2215(4) 0.1730(3) 0.0694(10) Uani 1 1 d . . . . .
H15 H 0.244742 0.133775 0.146679 0.083 Uiso 1 1 calc R U . . .
C16 C 0.1331(4) 0.2850(4) 0.0941(3) 0.0692(10) Uani 1 1 d . . . . .
C17 C 0.0990(5) 0.2159(4) -0.0322(3) 0.1002(13) Uani 1 1 d . . . . .
H17A H 0.043929 0.276212 -0.072359 0.150 Uiso 1 1 calc R U . . .
H17B H 0.025048 0.118991 -0.051090 0.150 Uiso 1 1 calc R U . . .
H17C H 0.206281 0.208590 -0.053481 0.150 Uiso 1 1 calc R U . . .
C18 C 0.0873(4) 0.4152(4) 0.1353(3) 0.0667(9) Uani 1 1 d . . . . .
H18 H 0.034802 0.461300 0.084833 0.080 Uiso 1 1 calc R U . . .
C19 C 0.1183(4) 0.4785(3) 0.2507(3) 0.0586(9) Uani 1 1 d . . . . .
C20 C 0.0901(4) 0.6939(4) 0.3899(3) 0.0571(9) Uani 1 1 d . . . . .
C21 C 0.1694(4) 0.6342(3) 0.4741(3) 0.0491(8) Uani 1 1 d . . . . .
C22 C 0.2071(4) 0.6861(3) 0.5919(3) 0.0515(8) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 112.6(3) . . ?
C20 O2 C19 122.6(3) . . ?
C22 N1 C4 107.7(2) . . ?
C22 N1 C3 126.2(2) . . ?
C4 N1 C3 126.0(3) . . ?
C22 N2 C10 110.1(2) . . ?
C22 N2 C9 109.3(3) . . ?
C10 N2 C9 140.5(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 110.2(3) . . ?
O1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
O1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N1 C3 C2 112.3(2) . . ?
N1 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
N1 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C9 119.9(3) . . ?
C5 C4 N1 131.3(3) . . ?
C9 C4 N1 108.8(3) . . ?
C6 C5 C4 118.1(3) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 121.8(3) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 116.2(3) . . ?
C7 C8 H8 121.9 . . ?
C9 C8 H8 121.9 . . ?
C8 C9 C4 122.7(3) . . ?
C8 C9 N2 131.7(3) . . ?
C4 C9 N2 105.6(3) . . ?
C11 C10 N2 107.5(2) . . ?
C11 C10 H10 126.3 . . ?
N2 C10 H10 126.3 . . ?
C10 C11 C21 107.8(3) . . ?
C10 C11 C12 134.4(3) . . ?
C21 C11 C12 117.9(3) . . ?
C19 C12 C13 116.5(3) . . ?
C19 C12 C11 116.9(3) . . ?
C13 C12 C11 126.6(3) . . ?
C15 C13 C12 119.4(3) . . ?
C15 C13 C14 119.5(3) . . ?
C12 C13 C14 121.1(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 123.2(3) . . ?
C16 C15 H15 118.4 . . ?
C13 C15 H15 118.4 . . ?
C18 C16 C15 117.2(3) . . ?
C18 C16 C17 120.7(3) . . ?
C15 C16 C17 122.1(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 120.8(3) . . ?
C16 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C12 123.0(3) . . ?
C18 C19 O2 113.8(3) . . ?
C12 C19 O2 123.3(3) . . ?
O3 C20 O2 115.7(3) . . ?
O3 C20 C21 128.6(3) . . ?
O2 C20 C21 115.7(3) . . ?
C22 C21 C20 130.1(3) . . ?
C22 C21 C11 106.2(3) . . ?
C20 C21 C11 123.6(3) . . ?
N1 C22 N2 108.6(2) . . ?
N1 C22 C21 143.0(3) . . ?
N2 C22 C21 108.4(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.399(3) . ?
O1 C1 1.406(4) . ?
O2 C20 1.386(3) . ?
O2 C19 1.397(3) . ?
O3 C20 1.217(3) . ?
N1 C22 1.361(3) . ?
N1 C4 1.392(3) . ?
N1 C3 1.460(3) . ?
N2 C22 1.363(3) . ?
N2 C10 1.387(3) . ?
N2 C9 1.397(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.496(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.379(4) . ?
C4 C9 1.386(4) . ?
C5 C6 1.371(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(4) . ?
C8 H8 0.9300 . ?
C10 C11 1.375(4) . ?
C10 H10 0.9300 . ?
C11 C21 1.446(4) . ?
C11 C12 1.446(4) . ?
C12 C19 1.389(4) . ?
C12 C13 1.414(4) . ?
C13 C15 1.387(4) . ?
C13 C14 1.510(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.385(4) . ?
C15 H15 0.9300 . ?
C16 C18 1.373(4) . ?
C16 C17 1.511(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.380(4) . ?
C18 H18 0.9300 . ?
C20 C21 1.412(4) . ?
C21 C22 1.391(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C2 C3 177.1(3) . . . . ?
C22 N1 C3 C2 -79.8(4) . . . . ?
C4 N1 C3 C2 95.9(3) . . . . ?
O1 C2 C3 N1 -65.9(3) . . . . ?
C22 N1 C4 C5 178.8(4) . . . . ?
C3 N1 C4 C5 2.5(5) . . . . ?
C22 N1 C4 C9 -1.3(3) . . . . ?
C3 N1 C4 C9 -177.7(3) . . . . ?
C9 C4 C5 C6 -1.2(5) . . . . ?
N1 C4 C5 C6 178.7(3) . . . . ?
C4 C5 C6 C7 -1.2(5) . . . . ?
C5 C6 C7 C8 2.2(6) . . . . ?
C6 C7 C8 C9 -0.7(6) . . . . ?
C7 C8 C9 C4 -1.7(5) . . . . ?
C7 C8 C9 N2 -179.9(4) . . . . ?
C5 C4 C9 C8 2.7(5) . . . . ?
N1 C4 C9 C8 -177.2(3) . . . . ?
C5 C4 C9 N2 -178.7(3) . . . . ?
N1 C4 C9 N2 1.4(3) . . . . ?
C22 N2 C9 C8 177.4(3) . . . . ?
C10 N2 C9 C8 -6.5(7) . . . . ?
C22 N2 C9 C4 -1.0(3) . . . . ?
C10 N2 C9 C4 175.1(4) . . . . ?
C22 N2 C10 C11 -0.8(3) . . . . ?
C9 N2 C10 C11 -176.8(4) . . . . ?
N2 C10 C11 C21 -0.2(3) . . . . ?
N2 C10 C11 C12 179.9(3) . . . . ?
C10 C11 C12 C19 176.4(3) . . . . ?
C21 C11 C12 C19 -3.5(4) . . . . ?
C10 C11 C12 C13 -3.6(5) . . . . ?
C21 C11 C12 C13 176.5(3) . . . . ?
C19 C12 C13 C15 -0.2(4) . . . . ?
C11 C12 C13 C15 179.8(3) . . . . ?
C19 C12 C13 C14 179.1(3) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C12 C13 C15 C16 -0.3(5) . . . . ?
C14 C13 C15 C16 -179.7(3) . . . . ?
C13 C15 C16 C18 0.6(5) . . . . ?
C13 C15 C16 C17 -179.7(3) . . . . ?
C15 C16 C18 C19 -0.4(5) . . . . ?
C17 C16 C18 C19 179.9(3) . . . . ?
C16 C18 C19 C12 -0.1(5) . . . . ?
C16 C18 C19 O2 180.0(3) . . . . ?
C13 C12 C19 C18 0.5(5) . . . . ?
C11 C12 C19 C18 -179.6(3) . . . . ?
C13 C12 C19 O2 -179.7(3) . . . . ?
C11 C12 C19 O2 0.3(4) . . . . ?
C20 O2 C19 C18 -177.3(3) . . . . ?
C20 O2 C19 C12 2.8(4) . . . . ?
C19 O2 C20 O3 177.8(3) . . . . ?
C19 O2 C20 C21 -2.3(4) . . . . ?
O3 C20 C21 C22 2.7(6) . . . . ?
O2 C20 C21 C22 -177.2(3) . . . . ?
O3 C20 C21 C11 178.7(3) . . . . ?
O2 C20 C21 C11 -1.2(4) . . . . ?
C10 C11 C21 C22 1.0(3) . . . . ?
C12 C11 C21 C22 -179.1(3) . . . . ?
C10 C11 C21 C20 -175.8(3) . . . . ?
C12 C11 C21 C20 4.1(4) . . . . ?
C4 N1 C22 N2 0.7(3) . . . . ?
C3 N1 C22 N2 177.1(3) . . . . ?
C4 N1 C22 C21 -177.0(4) . . . . ?
C3 N1 C22 C21 -0.7(6) . . . . ?
C10 N2 C22 N1 -177.2(3) . . . . ?
C9 N2 C22 N1 0.1(3) . . . . ?
C10 N2 C22 C21 1.4(3) . . . . ?
C9 N2 C22 C21 178.7(3) . . . . ?
C20 C21 C22 N1 -7.2(7) . . . . ?
C11 C21 C22 N1 176.3(4) . . . . ?
C20 C21 C22 N2 175.1(3) . . . . ?
C11 C21 C22 N2 -1.5(3) . . . . ?
