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#$Date: 2025-09-23 04:40:58 +0300 (Tue, 23 Sep 2025) $
#$Revision: 302222 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/08/7250895.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_7250895
loop_
_publ_author_name
'Feyzi, Aynaz'
'Jafarpour, Farnaz'
_publ_section_title
;
 Regioselective C3--C4 difunctionalization of 4-bromocoumarins via
 Pd/norbornene catalysis
;
_journal_issue                   41
_journal_name_full               'RSC Advances'
_journal_page_first              34434
_journal_page_last               34438
_journal_paper_doi               10.1039/D5RA05007C
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C20 H16 O4'
_chemical_formula_sum            'C20 H16 O4'
_chemical_formula_weight         320.33
_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     dual
_audit_creation_date             2020-08-27
_audit_creation_method
;

;
_audit_update_record
;
2025-03-11 deposited with the CCDC.	2025-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                72.75(3)
_cell_angle_beta                 85.55(3)
_cell_angle_gamma                86.34(3)
_cell_formula_units_Z            2
_cell_length_a                   5.6698(11)
_cell_length_b                   10.893(2)
_cell_length_c                   13.585(3)
_cell_measurement_reflns_used    4677
_cell_measurement_temperature    290
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.8
_cell_volume                     798.1(3)
_computing_cell_refinement       'Automar software package (3.3a, 2015)'
_computing_data_collection       'MAR345 dtb Program (1.24-4, 2013)'
_computing_data_reduction        'Automar software package (3.3a, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'PLATON (2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      290
_diffrn_detector                 'image-plate detector'
_diffrn_detector_area_resol_mean 0.81
_diffrn_detector_type            MAR345-dtb
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_device       'one-circle diffractometer'
_diffrn_measurement_device_type  MAR345
_diffrn_measurement_method       'image-plate detector - phi oscillation'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.883
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4747
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.850
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.21562
_exptl_absorpt_correction_T_min  0.86684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'R.H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0772
_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)+(0.1023P)²+0.4574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2176
_refine_ls_wR_factor_ref         0.2259
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2057
_reflns_number_total             2478
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ra05007c2.cif
_cod_data_source_block           1
_cod_database_code               7250895
_shelx_shelxl_version_number     2018/3
_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_max   0.986
_shelx_estimated_absorpt_t_min   0.973
_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C16(H16), C18(H18), C19(H19), C11(H11), C20(H20), C17(H17), C9(H9),
 C6(H6), C8(H8), C7(H7)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_submission_special_instructions 'No special instructions were received'
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
O3 O -0.0324(4) 0.7098(2) 0.51948(18) 0.0626(7) Uani 1 1 d . . . . .
O4 O 0.1848(5) 0.5255(2) 0.57408(19) 0.0688(8) Uani 1 1 d . . . . .
O1 O 0.7766(4) 0.9448(2) 0.09601(18) 0.0595(7) Uani 1 1 d . . . . .
O2 O 0.6086(5) 0.8446(3) 0.00324(19) 0.0757(8) Uani 1 1 d . . . . .
C10 C 0.2835(6) 0.7942(3) 0.3526(2) 0.0519(8) Uani 1 1 d . . . . .
H10 H 0.147025 0.843440 0.360409 0.062 Uiso 1 1 calc R U . . .
C16 C 0.5513(6) 0.5383(3) 0.1983(3) 0.0531(8) Uani 1 1 d . . . . .
H16 H 0.639099 0.581792 0.231363 0.064 Uiso 1 1 calc R U . . .
C18 C 0.4974(6) 0.3496(3) 0.1476(3) 0.0603(9) Uani 1 1 d . . . . .
H18 H 0.546788 0.266917 0.146408 0.072 Uiso 1 1 calc R U . . .
C15 C 0.3474(5) 0.5970(3) 0.1521(2) 0.0475(7) Uani 1 1 d . . . . .
C19 C 0.2959(7) 0.4067(4) 0.1012(3) 0.0632(9) Uani 1 1 d . . . . .
H19 H 0.209192 0.363084 0.067860 0.076 Uiso 1 1 calc R U . . .
C2 C 0.4375(6) 0.8153(3) 0.1727(2) 0.0514(8) Uani 1 1 d . . . . .
C11 C 0.3167(6) 0.6842(3) 0.4221(2) 0.0561(8) Uani 1 1 d . . . . .
H11 H 0.453548 0.635468 0.414063 0.067 Uiso 1 1 calc R U . . .
C14 C 0.2560(6) 0.7301(3) 0.1551(3) 0.0568(8) Uani 1 1 d . . . . .
H14A H 0.185875 0.773465 0.090310 0.068 Uiso 1 1 calc R U . . .
H14B H 0.131096 0.720140 0.209562 0.068 Uiso 1 1 calc R U . . .
C1 C 0.6048(7) 0.8667(3) 0.0849(3) 0.0577(9) Uani 1 1 d . . . . .
C12 C 0.1529(6) 0.6305(3) 0.5133(2) 0.0531(8) Uani 1 1 d . . . . .
C20 C 0.2207(6) 0.5296(3) 0.1039(3) 0.0588(9) Uani 1 1 d . . . . .
H20 H 0.082856 0.567192 0.072687 0.071 Uiso 1 1 calc R U . . .
C3 C 0.4495(6) 0.8466(3) 0.2614(2) 0.0502(8) Uani 1 1 d . . . . .
C4 C 0.6246(6) 0.9355(3) 0.2690(2) 0.0518(8) Uani 1 1 d . . . . .
C17 C 0.6260(6) 0.4152(3) 0.1958(3) 0.0584(9) Uani 1 1 d . . . . .
H17 H 0.763634 0.377079 0.226818 0.070 Uiso 1 1 calc R U . . .
C5 C 0.7837(6) 0.9815(3) 0.1838(3) 0.0540(8) Uani 1 1 d . . . . .
C9 C 0.6471(7) 0.9777(3) 0.3557(3) 0.0626(9) Uani 1 1 d . . . . .
H9 H 0.545439 0.947939 0.413966 0.075 Uiso 1 1 calc R U . . .
C6 C 0.9590(6) 1.0654(3) 0.1848(3) 0.0619(9) Uani 1 1 d . . . . .
H6 H 1.063793 1.094347 0.127486 0.074 Uiso 1 1 calc R U . . .
C13 C -0.2103(7) 0.6610(4) 0.6021(3) 0.0703(10) Uani 1 1 d . . . . .
H13A H -0.291450 0.593839 0.588196 0.105 Uiso 1 1 calc R U . . .
H13B H -0.321866 0.729492 0.606707 0.105 Uiso 1 1 calc R U . . .
H13C H -0.135454 0.627396 0.666270 0.105 Uiso 1 1 calc R U . . .
C8 C 0.8162(7) 1.0619(3) 0.3561(3) 0.0683(10) Uani 1 1 d . . . . .
H8 H 0.825190 1.090681 0.413642 0.082 Uiso 1 1 calc R U . . .
C7 C 0.9754(7) 1.1047(3) 0.2703(3) 0.0709(11) Uani 1 1 d . . . . .
H7 H 1.092574 1.159986 0.271671 0.085 Uiso 1 1 calc R U . . .
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'
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
C12 O3 C13 116.2(3) . . ?
C5 O1 C1 121.8(3) . . ?
C11 C10 H10 117.8 . . ?
C11 C10 C3 124.3(3) . . ?
C3 C10 H10 117.8 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.7(3) . . ?
C17 C16 H16 119.6 . . ?
C19 C18 H18 120.2 . . ?
C19 C18 C17 119.6(3) . . ?
C17 C18 H18 120.2 . . ?
C16 C15 C14 122.5(3) . . ?
C20 C15 C16 118.2(3) . . ?
C20 C15 C14 119.3(3) . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C1 C2 C14 115.2(3) . . ?
C3 C2 C14 124.5(3) . . ?
C3 C2 C1 120.3(3) . . ?
C10 C11 H11 117.5 . . ?
C10 C11 C12 125.0(3) . . ?
C12 C11 H11 117.5 . . ?
C15 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
C2 C14 C15 115.8(3) . . ?
C2 C14 H14A 108.3 . . ?
C2 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
O1 C1 C2 118.3(3) . . ?
O2 C1 O1 116.5(3) . . ?
O2 C1 C2 125.2(3) . . ?
O3 C12 C11 112.6(3) . . ?
O4 C12 O3 124.2(3) . . ?
O4 C12 C11 123.1(3) . . ?
C15 C20 C19 121.0(3) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C2 C3 C10 121.5(3) . . ?
C2 C3 C4 120.3(3) . . ?
C4 C3 C10 118.2(3) . . ?
C5 C4 C3 117.7(3) . . ?
C5 C4 C9 117.2(3) . . ?
C9 C4 C3 125.0(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
O1 C5 C4 121.4(3) . . ?
O1 C5 C6 116.9(3) . . ?
C6 C5 C4 121.6(3) . . ?
C4 C9 H9 119.4 . . ?
C8 C9 C4 121.2(3) . . ?
C8 C9 H9 119.4 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 120.2 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C8 H8 119.9 . . ?
C9 C8 C7 120.2(4) . . ?
C7 C8 H8 119.9 . . ?
C6 C7 C8 120.2(4) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
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
O3 C12 1.330(4) . ?
O3 C13 1.449(4) . ?
O4 C12 1.208(4) . ?
O1 C1 1.378(4) . ?
O1 C5 1.370(4) . ?
O2 C1 1.202(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.301(4) . ?
C10 C3 1.488(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.386(5) . ?
C16 C17 1.390(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(5) . ?
C18 C17 1.375(5) . ?
C15 C14 1.519(5) . ?
C15 C20 1.382(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(5) . ?
C2 C14 1.507(5) . ?
C2 C1 1.460(5) . ?
C2 C3 1.354(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.483(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C20 H20 0.9300 . ?
C3 C4 1.460(5) . ?
C4 C5 1.399(5) . ?
C4 C9 1.402(5) . ?
C17 H17 0.9300 . ?
C5 C6 1.395(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.370(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.363(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C8 H8 0.9300 . ?
C8 C7 1.400(6) . ?
C7 H7 0.9300 . ?
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
O1 C5 C6 C7 -179.7(3) . . . . ?
C10 C11 C12 O3 -2.3(5) . . . . ?
C10 C11 C12 O4 176.9(4) . . . . ?
C10 C3 C4 C5 178.4(3) . . . . ?
C10 C3 C4 C9 -1.1(5) . . . . ?
C16 C15 C14 C2 23.0(4) . . . . ?
C16 C15 C20 C19 -0.3(5) . . . . ?
C18 C19 C20 C15 0.6(5) . . . . ?
C15 C16 C17 C18 -0.3(5) . . . . ?
C19 C18 C17 C16 0.5(5) . . . . ?
C2 C3 C4 C5 -2.8(4) . . . . ?
C2 C3 C4 C9 177.7(3) . . . . ?
C11 C10 C3 C2 86.0(4) . . . . ?
C11 C10 C3 C4 -95.2(4) . . . . ?
C14 C15 C20 C19 -178.7(3) . . . . ?
C14 C2 C1 O1 -179.6(3) . . . . ?
C14 C2 C1 O2 -1.1(5) . . . . ?
C14 C2 C3 C10 2.0(5) . . . . ?
C14 C2 C3 C4 -176.8(3) . . . . ?
C1 O1 C5 C4 3.7(4) . . . . ?
C1 O1 C5 C6 -177.2(3) . . . . ?
C1 C2 C14 C15 73.1(4) . . . . ?
C1 C2 C3 C10 -179.1(3) . . . . ?
C1 C2 C3 C4 2.1(4) . . . . ?
C20 C15 C14 C2 -158.7(3) . . . . ?
C3 C10 C11 C12 -179.9(3) . . . . ?
C3 C2 C14 C15 -108.0(4) . . . . ?
C3 C2 C1 O1 1.4(4) . . . . ?
C3 C2 C1 O2 179.9(3) . . . . ?
C3 C4 C5 O1 0.0(4) . . . . ?
C3 C4 C5 C6 -179.1(3) . . . . ?
C3 C4 C9 C8 -179.7(3) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
C4 C9 C8 C7 -1.9(6) . . . . ?
C17 C16 C15 C14 178.5(3) . . . . ?
C17 C16 C15 C20 0.2(5) . . . . ?
C17 C18 C19 C20 -0.7(5) . . . . ?
C5 O1 C1 O2 177.0(3) . . . . ?
C5 O1 C1 C2 -4.3(4) . . . . ?
C5 C4 C9 C8 0.8(5) . . . . ?
C5 C6 C7 C8 -0.5(5) . . . . ?
C9 C4 C5 O1 179.5(3) . . . . ?
C9 C4 C5 C6 0.4(5) . . . . ?
C9 C8 C7 C6 1.7(6) . . . . ?
C13 O3 C12 O4 -3.4(5) . . . . ?
C13 O3 C12 C11 175.7(3) . . . . ?
