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#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/94/7119483.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_7119483
loop_
_publ_author_name
Hikaru
Yanai
Nobuyuki
Ishii
Takashi
Matsumoto
_publ_section_title
;
 Synthesis of 1,2,3,4-tetrasubstituted naphthalenes through a cascade
 reaction triggered by silyl acetal activation
;
_journal_name_full               Chem.Commun.
_journal_page_first              7974
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration .
_chemical_formula_moiety         'C25 H16 O3'
_chemical_formula_sum            'C25 H16 O3'
_chemical_formula_weight         364.38
_chemical_melting_point          178
_chemical_name_systematic
;
11-Benzoyl-6-hydroxytetracen-5(12H)-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             'August 21 2014'
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-03-21 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.869(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.507(4)
_cell_length_b                   8.1552(14)
_cell_length_c                   16.661(3)
_cell_measurement_reflns_used    2632
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.45
_cell_volume                     3461.4(10)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8153
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0404P)²+1.9447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                2504
_reflns_number_total             3046
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc03510h2.cif
_cod_data_source_block           CBA13-11
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7119483
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.23184(5) 0.69087(17) 0.34501(8) 0.0164(3) Uani 1 1 d . . .
C2 C 0.21794(5) 0.62204(17) 0.42270(8) 0.0157(3) Uani 1 1 d . . .
C3 C 0.16767(6) 0.64941(18) 0.45000(9) 0.0193(3) Uani 1 1 d . . .
H3 H 0.1431 0.7124 0.4183 0.023 Uiso 1 1 calc R . .
C4 C 0.15352(6) 0.58568(18) 0.52244(9) 0.0216(3) Uani 1 1 d . . .
H4 H 0.1194 0.6050 0.5410 0.026 Uiso 1 1 calc R . .
C5 C 0.18979(6) 0.49265(18) 0.56816(9) 0.0216(3) Uani 1 1 d . . .
H5 H 0.1803 0.4481 0.6181 0.026 Uiso 1 1 calc R . .
C6 C 0.23944(6) 0.46469(17) 0.54148(9) 0.0195(3) Uani 1 1 d . . .
H6 H 0.2637 0.4007 0.5733 0.023 Uiso 1 1 calc R . .
C7 C 0.25444(5) 0.52908(17) 0.46852(8) 0.0162(3) Uani 1 1 d . . .
C8 C 0.30900(5) 0.49720(17) 0.44188(8) 0.0163(3) Uani 1 1 d . . .
H8A H 0.3143 0.3771 0.4398 0.020 Uiso 1 1 calc R . .
H8B H 0.3343 0.5412 0.4834 0.020 Uiso 1 1 calc R . .
C9 C 0.32232(5) 0.56833(16) 0.36176(8) 0.0143(3) Uani 1 1 d . . .
C10 C 0.37108(5) 0.54236(17) 0.33222(8) 0.0153(3) Uani 1 1 d . . .
C11 C 0.38286(5) 0.59758(17) 0.25347(8) 0.0160(3) Uani 1 1 d . . .
C12 C 0.43114(6) 0.56509(18) 0.21839(9) 0.0194(3) Uani 1 1 d . . .
H12 H 0.4573 0.5041 0.2479 0.023 Uiso 1 1 calc R . .
C13 C 0.44103(6) 0.61957(18) 0.14290(9) 0.0210(3) Uani 1 1 d . . .
H13 H 0.4734 0.5933 0.1203 0.025 Uiso 1 1 calc R . .
C14 C 0.40366(6) 0.71398(18) 0.09848(9) 0.0196(3) Uani 1 1 d . . .
H14 H 0.4112 0.7537 0.0467 0.024 Uiso 1 1 calc R . .
C15 C 0.35659(6) 0.74822(17) 0.13015(8) 0.0174(3) Uani 1 1 d . . .
H15 H 0.3314 0.8121 0.1001 0.021 Uiso 1 1 calc R . .
C16 C 0.34490(5) 0.68971(16) 0.20721(8) 0.0156(3) Uani 1 1 d . . .
C17 C 0.29556(5) 0.72056(16) 0.23995(8) 0.0150(3) Uani 1 1 d . . .
C18 C 0.28378(5) 0.65945(16) 0.31523(8) 0.0147(3) Uani 1 1 d . . .
C19 C 0.41447(5) 0.46699(18) 0.38556(8) 0.0169(3) Uani 1 1 d . . .
C20 C 0.43380(5) 0.29874(17) 0.36857(8) 0.0173(3) Uani 1 1 d . . .
C21 C 0.40840(6) 0.20003(18) 0.31040(9) 0.0199(3) Uani 1 1 d . . .
H21 H 0.3788 0.2410 0.2798 0.024 Uiso 1 1 calc R . .
C22 C 0.42628(6) 0.04200(18) 0.29708(10) 0.0252(4) Uani 1 1 d . . .
H22 H 0.4087 -0.0256 0.2578 0.030 Uiso 1 1 calc R . .
C23 C 0.46975(6) -0.0168(2) 0.34114(10) 0.0281(4) Uani 1 1 d . . .
H23 H 0.4818 -0.1253 0.3323 0.034 Uiso 1 1 calc R . .
C24 C 0.47806(6) 0.23885(19) 0.41231(9) 0.0210(3) Uani 1 1 d . . .
H24 H 0.4958 0.3059 0.4516 0.025 Uiso 1 1 calc R . .
C25 C 0.49579(6) 0.0816(2) 0.39810(10) 0.0267(4) Uani 1 1 d . . .
H25 H 0.5259 0.0409 0.4275 0.032 Uiso 1 1 calc R . .
O1 O 0.26085(4) 0.80846(12) 0.19490(6) 0.0201(2) Uani 1 1 d . . .
O2 O 0.19904(4) 0.77598(12) 0.30518(6) 0.0215(3) Uani 1 1 d . . .
O3 O 0.43334(4) 0.54713(13) 0.44188(6) 0.0234(3) Uani 1 1 d . . .
H1 H 0.2300(7) 0.814(2) 0.2284(11) 0.035 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 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
O2 C1 C18 120.72(13) . .
O2 C1 C2 119.62(13) . .
C18 C1 C2 119.66(12) . .
C7 C2 C3 120.34(13) . .
C7 C2 C1 120.30(13) . .
C3 C2 C1 119.36(13) . .
C4 C3 C2 120.57(14) . .
C4 C3 H3 119.7 . .
C2 C3 H3 119.7 . .
C3 C4 C5 119.22(14) . .
C3 C4 H4 120.4 . .
C5 C4 H4 120.4 . .
C6 C5 C4 120.54(14) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C5 C6 C7 120.93(14) . .
C5 C6 H6 119.5 . .
C7 C6 H6 119.5 . .
C6 C7 C2 118.41(13) . .
C6 C7 C8 119.36(13) . .
C2 C7 C8 122.24(13) . .
C7 C8 C9 116.54(12) . .
C7 C8 H8A 108.2 . .
C9 C8 H8A 108.2 . .
C7 C8 H8B 108.2 . .
C9 C8 H8B 108.2 . .
H8A C8 H8B 107.3 . .
C10 C9 C18 119.68(13) . .
C10 C9 C8 120.28(12) . .
C18 C9 C8 120.02(12) . .
C9 C10 C11 120.90(13) . .
C9 C10 C19 119.96(12) . .
C11 C10 C19 118.95(12) . .
C12 C11 C16 117.30(13) . .
C12 C11 C10 123.11(13) . .
C16 C11 C10 119.59(13) . .
C13 C12 C11 121.53(13) . .
C13 C12 H12 119.2 . .
C11 C12 H12 119.2 . .
C12 C13 C14 120.65(14) . .
C12 C13 H13 119.7 . .
C14 C13 H13 119.7 . .
C15 C14 C13 119.66(14) . .
C15 C14 H14 120.2 . .
C13 C14 H14 120.2 . .
C14 C15 C16 120.75(13) . .
C14 C15 H15 119.6 . .
C16 C15 H15 119.6 . .
C15 C16 C17 121.35(13) . .
C15 C16 C11 120.07(13) . .
C17 C16 C11 118.59(13) . .
O1 C17 C18 121.90(13) . .
O1 C17 C16 116.97(12) . .
C18 C17 C16 121.13(13) . .
C17 C18 C9 119.98(13) . .
C17 C18 C1 118.83(13) . .
C9 C18 C1 121.19(13) . .
O3 C19 C20 121.12(13) . .
O3 C19 C10 118.79(13) . .
C20 C19 C10 120.08(12) . .
C21 C20 C24 119.65(14) . .
C21 C20 C19 121.13(13) . .
C24 C20 C19 119.21(13) . .
C22 C21 C20 120.13(14) . .
C22 C21 H21 119.9 . .
C20 C21 H21 119.9 . .
C23 C22 C21 119.85(15) . .
C23 C22 H22 120.1 . .
C21 C22 H22 120.1 . .
C22 C23 C25 120.37(15) . .
C22 C23 H23 119.8 . .
C25 C23 H23 119.8 . .
C25 C24 C20 119.72(14) . .
C25 C24 H24 120.1 . .
C20 C24 H24 120.1 . .
C24 C25 C23 120.26(15) . .
C24 C25 H25 119.9 . .
C23 C25 H25 119.9 . .
C17 O1 H1 103.4(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O2 1.2515(17) .
C1 C18 1.460(2) .
C1 C2 1.470(2) .
C2 C7 1.398(2) .
C2 C3 1.3999(19) .
C3 C4 1.379(2) .
C3 H3 0.9500 .
C4 C5 1.393(2) .
C4 H4 0.9500 .
C5 C6 1.382(2) .
C5 H5 0.9500 .
C6 C7 1.395(2) .
C6 H6 0.9500 .
C7 C8 1.5043(19) .
C8 C9 1.510(2) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.377(2) .
C9 C18 1.4294(19) .
C10 C11 1.433(2) .
C10 C19 1.5146(19) .
C11 C12 1.414(2) .
C11 C16 1.4219(19) .
C12 C13 1.369(2) .
C12 H12 0.9500 .
C13 C14 1.407(2) .
C13 H13 0.9500 .
C14 C15 1.364(2) .
C14 H14 0.9500 .
C15 C16 1.415(2) .
C15 H15 0.9500 .
C16 C17 1.419(2) .
C17 O1 1.3396(17) .
C17 C18 1.396(2) .
C19 O3 1.2223(17) .
C19 C20 1.490(2) .
C20 C21 1.394(2) .
C20 C24 1.401(2) .
C21 C22 1.389(2) .
C21 H21 0.9500 .
C22 C23 1.385(2) .
C22 H22 0.9500 .
C23 C25 1.387(2) .
C23 H23 0.9500 .
C24 C25 1.385(2) .
C24 H24 0.9500 .
C25 H25 0.9500 .
O1 H1 0.987(18) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139187355
