#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/53/1545328.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_1545328
loop_
_publ_author_name
'Kaida, Hiroyuki'
'Goya, Tsuyoshi'
'Nishii, Yuji'
'Hirano, Koji'
'Satoh, Tetsuya'
'Miura, Masahiro'
_publ_section_title
;
 Construction of Bisbenzofuro[2,3-b:3',2'-e]pyridines by
 Palladium-Catalyzed Double Intramolecular Oxidative C-H/C-H Coupling.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1236
_journal_page_last               1239
_journal_paper_doi               10.1021/acs.orglett.7b00323
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C25 H25 N O2'
_chemical_formula_sum            'C25 H25 N O2'
_chemical_formula_weight         371.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 100.414(9)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   9.1592(18)
_cell_length_b                   6.7731(12)
_cell_length_c                   16.695(3)
_cell_measurement_reflns_used    2235
_cell_measurement_temperature    273
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.01
_cell_volume                     1018.6(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15'
_computing_molecular_graphics    'CrystalStructure 4.2.1'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273
_diffrn_detector_area_resol_mean 13.653
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10919
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         3.040
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             396.00
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2525
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0666P)²+0.3007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2001
_reflns_number_total             2525
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ol7b00323_si_002.cif
_cod_data_source_block           201654
_cod_depositor_comments          'Adding full bibliography for 1545328.cif.'
_cod_database_code               1545328
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
3 -X,-Y,-Z
4 +X,-1/2-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
O1 O 0.37748(15) 0.2500 0.37131(9) 0.0322(4) Uani 1 2 d S T P
O2 O 0.28635(16) 0.2500 0.63722(9) 0.0344(4) Uani 1 2 d S T P
N3 N 0.31348(19) 0.2500 0.50057(11) 0.0314(4) Uani 1 2 d S T P
C4 C 0.6331(2) 0.2500 0.40525(12) 0.0273(4) Uani 1 2 d S T P
C5 C 0.5728(2) 0.2500 0.47958(13) 0.0276(4) Uani 1 2 d S T P
C6 C 0.5269(2) 0.2500 0.61403(13) 0.0289(5) Uani 1 2 d S T P
C7 C 0.6299(2) 0.2500 0.56257(13) 0.0290(4) Uani 1 2 d S T P
H7 H 0.7316 0.2500 0.5825 0.035 Uiso 1 2 calc R U P
C8 C 0.7745(2) 0.2500 0.38665(13) 0.0297(5) Uani 1 2 d S T P
H8 H 0.8571 0.2500 0.4283 0.036 Uiso 1 2 calc R U P
C9 C 0.5101(2) 0.2500 0.34157(13) 0.0289(4) Uani 1 2 d S T P
C10 C 0.7930(2) 0.2500 0.30559(13) 0.0299(5) Uani 1 2 d S T P
C11 C 0.5316(2) 0.2500 0.70113(13) 0.0309(5) Uani 1 2 d S T P
C12 C 0.4175(2) 0.2500 0.45474(13) 0.0292(5) Uani 1 2 d S T P
C13 C 0.6662(2) 0.2500 0.24426(13) 0.0314(5) Uani 1 2 d S T P
H13 H 0.6783 0.2500 0.1901 0.038 Uiso 1 2 calc R U P
C14 C 0.5226(2) 0.2500 0.26136(13) 0.0321(5) Uani 1 2 d S T P
H14 H 0.4394 0.2500 0.2201 0.038 Uiso 1 2 calc R U P
C15 C 0.3749(2) 0.2500 0.57885(14) 0.0303(5) Uani 1 2 d S T P
C16 C 0.3841(2) 0.2500 0.71141(14) 0.0324(5) Uani 1 2 d S T P
C17 C 0.6449(3) 0.2500 0.76914(13) 0.0342(5) Uani 1 2 d S T P
H17 H 0.7436 0.2500 0.7627 0.041 Uiso 1 2 calc R U P
C18 C 0.9507(2) 0.2500 0.28693(14) 0.0346(5) Uani 1 2 d S T P
C19 C 0.6098(3) 0.2500 0.84687(13) 0.0361(5) Uani 1 2 d S T P
C20 C 0.3443(3) 0.2500 0.78692(15) 0.0381(5) Uani 1 2 d S T P
H20 H 0.2453 0.2500 0.7928 0.046 Uiso 1 2 calc R U P
C21 C 1.03316(17) 0.4352(2) 0.32435(11) 0.0429(4) Uani 1 1 d . . .
H21A H 1.0339 0.4374 0.3819 0.052 Uiso 1 1 calc R U .
H21B H 1.1334 0.4329 0.3148 0.052 Uiso 1 1 calc R U .
H21C H 0.9837 0.5510 0.2997 0.052 Uiso 1 1 calc R U .
C22 C 0.4585(3) 0.2500 0.85382(15) 0.0400(6) Uani 1 2 d S T P
H22 H 0.4344 0.2500 0.9056 0.048 Uiso 1 2 calc R U P
C23 C 0.7301(3) 0.2500 0.92413(14) 0.0441(6) Uani 1 2 d S T P
C24 C 0.9510(3) 0.2500 0.19556(17) 0.0558(8) Uani 1 2 d S T P
C25 C 0.8870(4) 0.2500 0.9056(2) 0.0804(13) Uani 1 2 d S T P
C26 C 0.7146(3) 0.4332(5) 0.97438(16) 0.1056(11) Uani 1 1 d . . .
H26A H 0.7244 0.5489 0.9426 0.127 Uiso 1 1 calc R U .
H26B H 0.6189 0.4333 0.9902 0.127 Uiso 1 1 calc R U .
H26C H 0.7906 0.4333 1.0222 0.127 Uiso 1 1 calc R U .
H27 H 1.056(4) 0.2500 0.1868(18) 0.070(9) Uiso 1 2 d S . P
H28 H 0.901(2) 0.368(3) 0.1688(12) 0.067(6) Uiso 1 1 d . . .
H29 H 0.960(4) 0.2500 0.959(2) 0.094(12) Uiso 1 2 d S . P
H30 H 0.894(4) 0.373(5) 0.874(2) 0.145(14) Uiso 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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(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
C12 O1 C9 105.72(15) . .
C15 O2 C16 105.27(16) . .
C12 N3 C15 110.33(18) . .
C8 C4 C9 119.05(19) . .
C8 C4 C5 135.22(19) . .
C9 C4 C5 105.73(18) . .
C7 C5 C12 118.17(19) . .
C7 C5 C4 136.19(19) . .
C12 C5 C4 105.64(18) . .
C7 C6 C15 118.3(2) . .
C7 C6 C11 136.3(2) . .
C15 C6 C11 105.43(19) . .
C6 C7 C5 116.23(19) . .
C6 C7 H7 121.9 . .
C5 C7 H7 121.9 . .
C4 C8 C10 120.02(19) . .
C4 C8 H8 120.0 . .
C10 C8 H8 120.0 . .
C14 C9 O1 125.65(19) . .
C14 C9 C4 123.1(2) . .
O1 C9 C4 111.26(18) . .
C8 C10 C13 118.6(2) . .
C8 C10 C18 118.82(18) . .
C13 C10 C18 122.6(2) . .
C16 C11 C17 119.7(2) . .
C16 C11 C6 105.72(19) . .
C17 C11 C6 134.5(2) . .
N3 C12 O1 119.80(18) . .
N3 C12 C5 128.6(2) . .
O1 C12 C5 111.63(18) . .
C14 C13 C10 122.5(2) . .
C14 C13 H13 118.8 . .
C10 C13 H13 118.8 . .
C9 C14 C13 116.74(19) . .
C9 C14 H14 121.6 . .
C13 C14 H14 121.6 . .
N3 C15 O2 119.89(18) . .
N3 C15 C6 128.4(2) . .
O2 C15 C6 111.67(19) . .
C20 C16 O2 125.6(2) . .
C20 C16 C11 122.5(2) . .
O2 C16 C11 111.90(19) . .
C19 C17 C11 119.8(2) . .
C19 C17 H17 120.1 . .
C11 C17 H17 120.1 . .
C24 C18 C10 112.08(19) . .
C24 C18 C21 108.45(13) . 4_565
C10 C18 C21 109.24(12) . 4_565
C24 C18 C21 108.45(13) . .
C10 C18 C21 109.24(12) . .
C21 C18 C21 109.34(18) 4_565 .
C17 C19 C22 118.2(2) . .
C17 C19 C23 122.0(2) . .
C22 C19 C23 119.8(2) . .
C16 C20 C22 116.9(2) . .
C16 C20 H20 121.5 . .
C22 C20 H20 121.5 . .
C18 C21 H21A 109.5 . .
C18 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C18 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C20 C22 C19 122.9(2) . .
C20 C22 H22 118.6 . .
C19 C22 H22 118.6 . .
C26 C23 C26 109.6(3) 4_565 .
C26 C23 C25 107.35(19) 4_565 .
C26 C23 C25 107.35(19) . .
C26 C23 C19 109.80(16) 4_565 .
C26 C23 C19 109.80(16) . .
C25 C23 C19 112.9(2) . .
C18 C24 H27 108.8(17) . .
C18 C24 H28 111.6(12) . .
H27 C24 H28 108.1(15) . .
C23 C25 H29 108(2) . .
C23 C25 H30 105.0(19) . .
H29 C25 H30 112(2) . .
C23 C26 H26A 109.5 . .
C23 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C23 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C12 1.375(2) .
O1 C9 1.393(3) .
O2 C15 1.376(3) .
O2 C16 1.391(3) .
N3 C12 1.325(3) .
N3 C15 1.326(3) .
C4 C8 1.385(3) .
C4 C9 1.402(3) .
C4 C5 1.447(3) .
C5 C7 1.390(3) .
C5 C12 1.408(3) .
C6 C7 1.386(3) .
C6 C15 1.410(3) .
C6 C11 1.447(3) .
C7 H7 0.9300 .
C8 C10 1.394(3) .
C8 H8 0.9300 .
C9 C14 1.364(3) .
C10 C13 1.403(3) .
C10 C18 1.531(3) .
C11 C16 1.392(3) .
C11 C17 1.393(3) .
C13 C14 1.396(3) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C16 C20 1.374(3) .
C17 C19 1.392(3) .
C17 H17 0.9300 .
C18 C24 1.526(3) .
C18 C21 1.537(2) 4_565
C18 C21 1.537(2) .
C19 C22 1.411(3) .
C19 C23 1.538(3) .
C20 C22 1.385(4) .
C20 H20 0.9300 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C22 H22 0.9300 .
C23 C26 1.519(3) 4_565
C23 C26 1.519(3) .
C23 C25 1.523(5) .
C24 H27 0.99(3) .
C24 H28 0.99(2) .
C25 H29 1.01(4) .
C25 H30 0.99(3) .
C26 H26A 0.9600 .
C26 H26B 0.9600 .
C26 H26C 0.9600 .
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_4
C8 C4 C5 C7 0.000(1) .
C9 C4 C5 C7 180.000(1) .
C8 C4 C5 C12 180.000(1) .
C9 C4 C5 C12 0.000(0) .
C15 C6 C7 C5 0.000(1) .
C11 C6 C7 C5 180.000(1) .
C12 C5 C7 C6 0.000(1) .
C4 C5 C7 C6 180.000(1) .
C9 C4 C8 C10 0.000(1) .
C5 C4 C8 C10 180.000(1) .
C12 O1 C9 C14 180.000(0) .
C12 O1 C9 C4 0.000(0) .
C8 C4 C9 C14 0.000(1) .
C5 C4 C9 C14 180.000(0) .
C8 C4 C9 O1 180.000(0) .
C5 C4 C9 O1 0.000(0) .
C4 C8 C10 C13 0.000(0) .
C4 C8 C10 C18 180.000(0) .
C7 C6 C11 C16 180.000(1) .
C15 C6 C11 C16 0.000(1) .
C7 C6 C11 C17 0.000(1) .
C15 C6 C11 C17 180.000(1) .
C15 N3 C12 O1 180.000(0) .
C15 N3 C12 C5 0.000(1) .
C9 O1 C12 N3 180.000(0) .
C9 O1 C12 C5 0.000(0) .
C7 C5 C12 N3 0.000(1) .
C4 C5 C12 N3 180.000(1) .
C7 C5 C12 O1 180.000(1) .
C4 C5 C12 O1 0.000(0) .
C8 C10 C13 C14 0.000(0) .
C18 C10 C13 C14 180.000(0) .
O1 C9 C14 C13 180.000(0) .
C4 C9 C14 C13 0.000(1) .
C10 C13 C14 C9 0.000(0) .
C12 N3 C15 O2 180.000(1) .
C12 N3 C15 C6 0.000(1) .
C16 O2 C15 N3 180.000(1) .
C16 O2 C15 C6 0.000(1) .
C7 C6 C15 N3 0.000(1) .
C11 C6 C15 N3 180.000(1) .
C7 C6 C15 O2 180.000(1) .
C11 C6 C15 O2 0.000(1) .
C15 O2 C16 C20 180.000(1) .
C15 O2 C16 C11 0.000(1) .
C17 C11 C16 C20 0.000(1) .
C6 C11 C16 C20 180.000(1) .
C17 C11 C16 O2 180.000(1) .
C6 C11 C16 O2 0.000(1) .
C16 C11 C17 C19 0.000(1) .
C6 C11 C17 C19 180.000(1) .
C8 C10 C18 C24 180.000(0) .
C13 C10 C18 C24 0.000(0) .
C8 C10 C18 C21 59.78(13) 4_565
C13 C10 C18 C21 -120.22(13) 4_565
C8 C10 C18 C21 -59.78(13) .
C13 C10 C18 C21 120.22(13) .
C11 C17 C19 C22 0.000(1) .
C11 C17 C19 C23 180.000(1) .
O2 C16 C20 C22 180.000(1) .
C11 C16 C20 C22 0.000(1) .
C16 C20 C22 C19 0.000(2) .
C17 C19 C22 C20 0.000(1) .
C23 C19 C22 C20 180.000(1) .
C17 C19 C23 C26 -119.74(19) 4_565
C22 C19 C23 C26 60.26(19) 4_565
C17 C19 C23 C26 119.7(2) .
C22 C19 C23 C26 -60.3(2) .
C17 C19 C23 C25 0.000(2) .
C22 C19 C23 C25 180.000(1) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132605897
