#------------------------------------------------------------------------------
#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/94/7119484.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_7119484
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         'C27 H22 O4'
_chemical_formula_sum            'C27 H22 O4'
_chemical_formula_weight         410.45
_chemical_melting_point          133
_chemical_name_systematic
; 
Ethyl 4-benzoyl-3-benzyl-1-hydroxy-2-naphthoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             '01 May 2013'
_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                104.062(3)
_cell_angle_beta                 94.660(3)
_cell_angle_gamma                116.023(2)
_cell_formula_units_Z            2
_cell_length_a                   9.173(2)
_cell_length_b                   10.382(3)
_cell_length_c                   12.748(3)
_cell_measurement_reflns_used    4575
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.30
_cell_volume                     1033.4(4)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10078
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_correction_T_min  0.9758
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3635
_refine_ls_number_restraints     204
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0466
_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)+(0.0829P)²+0.2205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1368
_reflns_number_gt                3133
_reflns_number_total             3635
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc03510h2.cif
_cod_data_source_block           CBA13-9b
_cod_database_code               7119484
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.19475(18) 0.02295(16) 0.11873(11) 0.0183(3) Uani 1 1 d U . .
C2 C 0.34378(18) 0.16178(16) 0.17094(11) 0.0194(3) Uani 1 1 d U . .
C3 C 0.49849(18) 0.18332(17) 0.14539(13) 0.0244(3) Uani 1 1 d U . .
H3 H 0.5050 0.1040 0.0937 0.029 Uiso 1 1 calc R . .
C4 C 0.63925(19) 0.31853(18) 0.19509(14) 0.0283(4) Uani 1 1 d U . .
H4 H 0.7425 0.3334 0.1765 0.034 Uiso 1 1 calc R . .
C5 C 0.63085(19) 0.43504(18) 0.27348(13) 0.0290(4) Uani 1 1 d U . .
H5 H 0.7291 0.5278 0.3084 0.035 Uiso 1 1 calc R . .
C6 C 0.48275(18) 0.41635(17) 0.30003(12) 0.0251(4) Uani 1 1 d U . .
H6 H 0.4796 0.4963 0.3534 0.030 Uiso 1 1 calc R . .
C7 C 0.33389(17) 0.27933(16) 0.24897(11) 0.0191(3) Uani 1 1 d U . .
C8 C 0.17608(17) 0.25659(15) 0.27187(11) 0.0175(3) Uani 1 1 d U . .
C9 C 0.03144(17) 0.12563(15) 0.21907(11) 0.0167(3) Uani 1 1 d U . .
C10 C 0.04059(17) 0.00292(15) 0.14041(11) 0.0172(3) Uani 1 1 d U . .
C11 C 0.17317(17) 0.38203(15) 0.36140(11) 0.0190(3) Uani 1 1 d U . .
C12 C 0.14235(16) 0.49869(15) 0.32964(11) 0.0176(3) Uani 1 1 d U . .
C13 C 0.11991(17) 0.49680(15) 0.21985(12) 0.0202(3) Uani 1 1 d U . .
H13 H 0.1256 0.4211 0.1636 0.024 Uiso 1 1 calc R . .
C14 C 0.08918(18) 0.60535(17) 0.19249(12) 0.0240(3) Uani 1 1 d U . .
H14 H 0.0737 0.6042 0.1176 0.029 Uiso 1 1 calc R . .
C15 C 0.08115(18) 0.71559(16) 0.27508(13) 0.0244(3) Uani 1 1 d U . .
H15 H 0.0596 0.7896 0.2562 0.029 Uiso 1 1 calc R . .
C16 C 0.10411(17) 0.71927(16) 0.38473(12) 0.0223(3) Uani 1 1 d U . .
H16 H 0.0990 0.7957 0.4406 0.027 Uiso 1 1 calc R . .
C17 C 0.13454(17) 0.61079(15) 0.41261(12) 0.0198(3) Uani 1 1 d U . .
H17 H 0.1500 0.6125 0.4876 0.024 Uiso 1 1 calc R . .
C18 C -0.13079(17) 0.11704(15) 0.24422(12) 0.0185(3) Uani 1 1 d U . .
H18A H -0.2108 0.0780 0.1729 0.022 Uiso 1 1 calc R . .
H18B H -0.1105 0.2209 0.2807 0.022 Uiso 1 1 calc R . .
C19 C -0.21284(17) 0.02080(15) 0.31655(11) 0.0189(3) Uani 1 1 d U . .
C20 C -0.36881(18) 0.00019(17) 0.33334(12) 0.0245(3) Uani 1 1 d U . .
H20 H -0.4192 0.0489 0.3019 0.029 Uiso 1 1 calc R . .
C21 C -0.45134(19) -0.09090(18) 0.39558(13) 0.0298(4) Uani 1 1 d U . .
H21 H -0.5584 -0.1054 0.4054 0.036 Uiso 1 1 calc R . .
C22 C -0.3788(2) -0.16035(17) 0.44313(13) 0.0296(4) Uani 1 1 d U . .
H22 H -0.4356 -0.2224 0.4857 0.035 Uiso 1 1 calc R . .
C23 C -0.2225(2) -0.13928(17) 0.42862(13) 0.0275(4) Uani 1 1 d U . .
H23 H -0.1718 -0.1867 0.4613 0.033 Uiso 1 1 calc R . .
C24 C -0.14010(18) -0.04818(16) 0.36584(12) 0.0217(3) Uani 1 1 d U . .
H24 H -0.0326 -0.0332 0.3567 0.026 Uiso 1 1 calc R . .
C25 C -0.10386(18) -0.14711(15) 0.08298(11) 0.0182(3) Uani 1 1 d U . .
C26 C -0.38938(18) -0.31591(16) 0.05604(13) 0.0244(4) Uani 1 1 d U . .
H26A H -0.3641 -0.3877 0.0821 0.029 Uiso 1 1 calc R . .
H26B H -0.4118 -0.3485 -0.0259 0.029 Uiso 1 1 calc R . .
C27 C -0.5379(2) -0.31129(18) 0.09593(14) 0.0351(4) Uani 1 1 d U . .
H27A H -0.5177 -0.2869 0.1767 0.053 Uiso 1 1 calc R . .
H27B H -0.6365 -0.4099 0.0623 0.053 Uiso 1 1 calc R . .
H27C H -0.5562 -0.2340 0.0747 0.053 Uiso 1 1 calc R . .
O1 O -0.09046(13) -0.25258(11) 0.02283(8) 0.0232(3) Uani 1 1 d U . .
O2 O 0.21480(13) -0.08459(11) 0.04791(8) 0.0240(3) Uani 1 1 d U . .
H2 H 0.1225 -0.1625 0.0214 0.036 Uiso 1 1 calc R . .
O3 O 0.19929(15) 0.38724(12) 0.45773(8) 0.0308(3) Uani 1 1 d U . .
O4 O -0.24964(12) -0.16315(11) 0.10152(8) 0.0220(3) Uani 1 1 d 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
O2 C1 C10 123.26(13) . .
O2 C1 C2 115.15(12) . .
C10 C1 C2 121.60(13) . .
C3 C2 C7 120.08(13) . .
C3 C2 C1 121.29(13) . .
C7 C2 C1 118.62(13) . .
C4 C3 C2 120.20(14) . .
C4 C3 H3 119.9 . .
C2 C3 H3 119.9 . .
C3 C4 C5 120.06(14) . .
C3 C4 H4 120.0 . .
C5 C4 H4 120.0 . .
C6 C5 C4 120.72(14) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C5 C6 C7 120.95(14) . .
C5 C6 H6 119.5 . .
C7 C6 H6 119.5 . .
C2 C7 C6 117.96(13) . .
C2 C7 C8 119.25(12) . .
C6 C7 C8 122.78(13) . .
C9 C8 C7 122.49(12) . .
C9 C8 C11 120.15(12) . .
C7 C8 C11 117.32(12) . .
C8 C9 C10 118.69(13) . .
C8 C9 C18 118.19(12) . .
C10 C9 C18 123.12(12) . .
C1 C10 C9 119.28(12) . .
C1 C10 C25 116.42(12) . .
C9 C10 C25 124.26(12) . .
O3 C11 C12 121.19(12) . .
O3 C11 C8 119.36(12) . .
C12 C11 C8 119.44(12) . .
C13 C12 C17 119.92(13) . .
C13 C12 C11 121.26(12) . .
C17 C12 C11 118.81(13) . .
C14 C13 C12 120.05(13) . .
C14 C13 H13 120.0 . .
C12 C13 H13 120.0 . .
C15 C14 C13 119.64(14) . .
C15 C14 H14 120.2 . .
C13 C14 H14 120.2 . .
C16 C15 C14 120.91(14) . .
C16 C15 H15 119.5 . .
C14 C15 H15 119.5 . .
C15 C16 C17 119.72(13) . .
C15 C16 H16 120.1 . .
C17 C16 H16 120.1 . .
C16 C17 C12 119.75(13) . .
C16 C17 H17 120.1 . .
C12 C17 H17 120.1 . .
C9 C18 C19 117.11(11) . .
C9 C18 H18A 108.0 . .
C19 C18 H18A 108.0 . .
C9 C18 H18B 108.0 . .
C19 C18 H18B 108.0 . .
H18A C18 H18B 107.3 . .
C24 C19 C20 118.51(13) . .
C24 C19 C18 123.04(13) . .
C20 C19 C18 118.45(13) . .
C21 C20 C19 120.62(15) . .
C21 C20 H20 119.7 . .
C19 C20 H20 119.7 . .
C22 C21 C20 120.40(14) . .
C22 C21 H21 119.8 . .
C20 C21 H21 119.8 . .
C21 C22 C23 119.73(14) . .
C21 C22 H22 120.1 . .
C23 C22 H22 120.1 . .
C22 C23 C24 119.78(15) . .
C22 C23 H23 120.1 . .
C24 C23 H23 120.1 . .
C19 C24 C23 120.92(14) . .
C19 C24 H24 119.5 . .
C23 C24 H24 119.5 . .
O1 C25 O4 121.38(12) . .
O1 C25 C10 122.78(13) . .
O4 C25 C10 115.83(12) . .
O4 C26 C27 107.01(12) . .
O4 C26 H26A 110.3 . .
C27 C26 H26A 110.3 . .
O4 C26 H26B 110.3 . .
C27 C26 H26B 110.3 . .
H26A C26 H26B 108.6 . .
C26 C27 H27A 109.5 . .
C26 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C26 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C1 O2 H2 109.5 . .
C25 O4 C26 115.93(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O2 1.3464(17) .
C1 C10 1.397(2) .
C1 C2 1.430(2) .
C2 C3 1.415(2) .
C2 C7 1.417(2) .
C3 C4 1.372(2) .
C3 H3 0.9500 .
C4 C5 1.405(2) .
C4 H4 0.9500 .
C5 C6 1.369(2) .
C5 H5 0.9500 .
C6 C7 1.419(2) .
C6 H6 0.9500 .
C7 C8 1.428(2) .
C8 C9 1.3745(19) .
C8 C11 1.5207(19) .
C9 C10 1.4568(19) .
C9 C18 1.5167(19) .
C10 C25 1.4815(19) .
C11 O3 1.2153(17) .
C11 C12 1.494(2) .
C12 C13 1.392(2) .
C12 C17 1.4020(19) .
C13 C14 1.387(2) .
C13 H13 0.9500 .
C14 C15 1.387(2) .
C14 H14 0.9500 .
C15 C16 1.385(2) .
C15 H15 0.9500 .
C16 C17 1.388(2) .
C16 H16 0.9500 .
C17 H17 0.9500 .
C18 C19 1.5217(19) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C24 1.387(2) .
C19 C20 1.394(2) .
C20 C21 1.390(2) .
C20 H20 0.9500 .
C21 C22 1.377(2) .
C21 H21 0.9500 .
C22 C23 1.388(2) .
C22 H22 0.9500 .
C23 C24 1.395(2) .
C23 H23 0.9500 .
C24 H24 0.9500 .
C25 O1 1.2359(17) .
C25 O4 1.3217(17) .
C26 O4 1.4640(16) .
C26 C27 1.509(2) .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
O2 H2 0.8400 .
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
O2 C1 C2 C3 2.2(2) . . . .
C10 C1 C2 C3 -177.52(12) . . . .
O2 C1 C2 C7 -178.30(12) . . . .
C10 C1 C2 C7 2.0(2) . . . .
C7 C2 C3 C4 -0.7(2) . . . .
C1 C2 C3 C4 178.80(13) . . . .
C2 C3 C4 C5 1.4(2) . . . .
C3 C4 C5 C6 -1.0(2) . . . .
C4 C5 C6 C7 -0.2(2) . . . .
C3 C2 C7 C6 -0.5(2) . . . .
C1 C2 C7 C6 -179.98(13) . . . .
C3 C2 C7 C8 178.65(13) . . . .
C1 C2 C7 C8 -0.85(19) . . . .
C5 C6 C7 C2 0.9(2) . . . .
C5 C6 C7 C8 -178.16(13) . . . .
C2 C7 C8 C9 -1.6(2) . . . .
C6 C7 C8 C9 177.50(13) . . . .
C2 C7 C8 C11 176.23(12) . . . .
C6 C7 C8 C11 -4.7(2) . . . .
C7 C8 C9 C10 2.8(2) . . . .
C11 C8 C9 C10 -174.93(12) . . . .
C7 C8 C9 C18 -176.14(12) . . . .
C11 C8 C9 C18 6.11(19) . . . .
O2 C1 C10 C9 179.56(12) . . . .
C2 C1 C10 C9 -0.7(2) . . . .
O2 C1 C10 C25 1.6(2) . . . .
C2 C1 C10 C25 -178.71(12) . . . .
C8 C9 C10 C1 -1.64(19) . . . .
C18 C9 C10 C1 177.26(12) . . . .
C8 C9 C10 C25 176.16(12) . . . .
C18 C9 C10 C25 -4.9(2) . . . .
C9 C8 C11 O3 93.29(17) . . . .
C7 C8 C11 O3 -84.57(16) . . . .
C9 C8 C11 C12 -88.18(16) . . . .
C7 C8 C11 C12 93.96(15) . . . .
O3 C11 C12 C13 177.04(13) . . . .
C8 C11 C12 C13 -1.46(19) . . . .
O3 C11 C12 C17 -3.6(2) . . . .
C8 C11 C12 C17 177.91(12) . . . .
C17 C12 C13 C14 -0.3(2) . . . .
C11 C12 C13 C14 179.11(13) . . . .
C12 C13 C14 C15 0.1(2) . . . .
C13 C14 C15 C16 0.3(2) . . . .
C14 C15 C16 C17 -0.4(2) . . . .
C15 C16 C17 C12 0.2(2) . . . .
C13 C12 C17 C16 0.1(2) . . . .
C11 C12 C17 C16 -179.26(12) . . . .
C8 C9 C18 C19 -106.09(15) . . . .
C10 C9 C18 C19 75.00(17) . . . .
C9 C18 C19 C24 4.93(19) . . . .
C9 C18 C19 C20 -174.59(12) . . . .
C24 C19 C20 C21 -1.8(2) . . . .
C18 C19 C20 C21 177.78(13) . . . .
C19 C20 C21 C22 1.0(2) . . . .
C20 C21 C22 C23 -0.1(2) . . . .
C21 C22 C23 C24 -0.1(2) . . . .
C20 C19 C24 C23 1.6(2) . . . .
C18 C19 C24 C23 -177.95(13) . . . .
C22 C23 C24 C19 -0.7(2) . . . .
C1 C10 C25 O1 3.3(2) . . . .
C9 C10 C25 O1 -174.61(13) . . . .
C1 C10 C25 O4 -178.00(11) . . . .
C9 C10 C25 O4 4.1(2) . . . .
O1 C25 O4 C26 5.96(19) . . . .
C10 C25 O4 C26 -172.80(11) . . . .
C27 C26 O4 C25 174.63(12) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102130462
