#------------------------------------------------------------------------------
#$Date: 2023-06-09 09:40:09 +0300 (Fri, 09 Jun 2023) $
#$Revision: 284421 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107326.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_8107326
loop_
_publ_author_name
'Shin, Soon Young'
'Lee, Ha-Jin'
'Sung, Jiha'
'Koh, Dongsoo'
_publ_section_title
;
 The crystal structure of 2-(4-methoxynaphthalen-1-yl)-4H-chromen-4-one,
 C20H14O3
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1171
_journal_page_last               1173
_journal_paper_doi               10.1515/ncrs-2022-0446
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C20 H14 O3'
_chemical_formula_sum            'C20 H14 O3'
_chemical_formula_weight         302.31
_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
_cell_angle_alpha                91.691(5)
_cell_angle_beta                 107.708(5)
_cell_angle_gamma                113.607(5)
_cell_formula_units_Z            2
_cell_length_a                   8.3085(10)
_cell_length_b                   8.3918(8)
_cell_length_c                   12.1359(14)
_cell_measurement_reflns_used    7309
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      28.38
_cell_measurement_theta_min      2.79
_cell_volume                     727.42(15)
_computing_cell_refinement       'Bruker SAINT [1]'
_computing_data_collection       'Bruker APEX2 [1]'
_computing_data_reduction        'Bruker SAINT [1]'
_computing_molecular_graphics    'OLEX2 [4]'
_computing_publication_material  'OLEX2 [4]'
_computing_structure_refinement  'SHELXL-2014/7 [3]'
_computing_structure_solution    'Bruker SHELXTL [2]'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30362
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.567
_diffrn_reflns_theta_min         2.690
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       Block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0471
_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)+(0.0438P)²+0.3219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1235
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2605
_reflns_number_total             3696
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0446_suppl.cif
_cod_data_source_block           DK1915
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_cell_volume        727.42(14)
_cod_database_code               8107326
_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   0.980
_shelx_estimated_absorpt_t_max   0.990
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
C1 C 0.7412(2) 1.1182(2) 0.35417(14) 0.0337(3) Uani 1 1 d . . . . .
C2 C 0.6748(2) 0.9777(2) 0.25696(14) 0.0332(3) Uani 1 1 d . . . . .
H2 H 0.7629 0.9547 0.2341 0.040 Uiso 1 1 calc R U . . .
C3 C 0.4921(2) 0.8789(2) 0.19809(13) 0.0306(3) Uani 1 1 d . . . . .
O1 O 0.35604(15) 0.90392(15) 0.22624(10) 0.0378(3) Uani 1 1 d . . . . .
C4 C 0.4064(2) 1.0325(2) 0.31913(13) 0.0311(3) Uani 1 1 d . . . . .
C5 C 0.2595(2) 1.0474(2) 0.34379(15) 0.0412(4) Uani 1 1 d . . . . .
H5 H 0.1346 0.9717 0.2992 0.049 Uiso 1 1 calc R U . . .
C6 C 0.3008(3) 1.1747(3) 0.43452(16) 0.0451(4) Uani 1 1 d . . . . .
H6 H 0.2032 1.1868 0.4522 0.054 Uiso 1 1 calc R U . . .
C7 C 0.4852(3) 1.2861(2) 0.50060(15) 0.0419(4) Uani 1 1 d . . . . .
H7 H 0.5116 1.3732 0.5623 0.050 Uiso 1 1 calc R U . . .
C8 C 0.6299(2) 1.2698(2) 0.47627(14) 0.0373(4) Uani 1 1 d . . . . .
H8 H 0.7545 1.3450 0.5218 0.045 Uiso 1 1 calc R U . . .
C9 C 0.5918(2) 1.1410(2) 0.38363(13) 0.0302(3) Uani 1 1 d . . . . .
O2 O 0.90816(17) 1.21270(18) 0.40833(11) 0.0505(4) Uani 1 1 d . . . . .
C10 C 0.4128(2) 0.7363(2) 0.09618(13) 0.0301(3) Uani 1 1 d . . . . .
C11 C 0.4745(2) 0.7693(2) 0.00315(14) 0.0338(4) Uani 1 1 d . . . . .
H11 H 0.5706 0.8804 0.0078 0.041 Uiso 1 1 calc R U . . .
C12 C 0.3991(2) 0.6429(2) -0.09910(14) 0.0346(4) Uani 1 1 d . . . . .
H12 H 0.4431 0.6703 -0.1621 0.042 Uiso 1 1 calc R U . . .
C13 C 0.2617(2) 0.4801(2) -0.10625(13) 0.0315(3) Uani 1 1 d . . . . .
C14 C 0.1989(2) 0.4344(2) -0.00934(13) 0.0294(3) Uani 1 1 d . . . . .
C15 C 0.0657(2) 0.2631(2) -0.01243(15) 0.0369(4) Uani 1 1 d . . . . .
H15 H 0.0155 0.1770 -0.0800 0.044 Uiso 1 1 calc R U . . .
C16 C 0.0089(2) 0.2210(2) 0.08119(16) 0.0421(4) Uani 1 1 d . . . . .
H16 H -0.0788 0.1059 0.0781 0.050 Uiso 1 1 calc R U . . .
C17 C 0.0800(2) 0.3477(2) 0.18187(16) 0.0416(4) Uani 1 1 d . . . . .
H17 H 0.0399 0.3177 0.2461 0.050 Uiso 1 1 calc R U . . .
C18 C 0.2077(2) 0.5153(2) 0.18702(14) 0.0359(4) Uani 1 1 d . . . . .
H18 H 0.2536 0.5997 0.2549 0.043 Uiso 1 1 calc R U . . .
C19 C 0.2726(2) 0.5645(2) 0.09243(13) 0.0289(3) Uani 1 1 d . . . . .
O3 O 0.17446(17) 0.34911(15) -0.20199(10) 0.0414(3) Uani 1 1 d . . . . .
C20 C 0.2105(3) 0.3948(3) -0.30710(15) 0.0524(5) Uani 1 1 d . . . . .
H20A H 0.1807 0.4929 -0.3278 0.079 Uiso 1 1 calc R U . . .
H20B H 0.1338 0.2941 -0.3702 0.079 Uiso 1 1 calc R U . . .
H20C H 0.3416 0.4284 -0.2948 0.079 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
O2 C1 C2 123.65(15) . .
O2 C1 C9 122.08(14) . .
C2 C1 C9 114.27(13) . .
C3 C2 C1 122.44(14) . .
C3 C2 H2 118.8 . .
C1 C2 H2 118.8 . .
C2 C3 O1 122.21(14) . .
C2 C3 C10 125.84(14) . .
O1 C3 C10 111.94(13) . .
C3 O1 C4 119.31(12) . .
O1 C4 C9 122.04(13) . .
O1 C4 C5 115.85(14) . .
C9 C4 C5 122.11(14) . .
C6 C5 C4 118.60(16) . .
C6 C5 H5 120.7 . .
C4 C5 H5 120.7 . .
C5 C6 C7 120.68(16) . .
C5 C6 H6 119.7 . .
C7 C6 H6 119.7 . .
C8 C7 C6 120.41(16) . .
C8 C7 H7 119.8 . .
C6 C7 H7 119.8 . .
C7 C8 C9 120.15(16) . .
C7 C8 H8 119.9 . .
C9 C8 H8 119.9 . .
C4 C9 C8 118.04(14) . .
C4 C9 C1 119.72(13) . .
C8 C9 C1 122.24(14) . .
C11 C10 C19 119.32(14) . .
C11 C10 C3 119.11(14) . .
C19 C10 C3 121.57(13) . .
C10 C11 C12 122.29(15) . .
C10 C11 H11 118.9 . .
C12 C11 H11 118.9 . .
C13 C12 C11 119.50(14) . .
C13 C12 H12 120.3 . .
C11 C12 H12 120.3 . .
O3 C13 C12 124.72(14) . .
O3 C13 C14 114.48(14) . .
C12 C13 C14 120.80(14) . .
C15 C14 C19 119.31(14) . .
C15 C14 C13 121.52(14) . .
C19 C14 C13 119.17(14) . .
C16 C15 C14 120.81(15) . .
C16 C15 H15 119.6 . .
C14 C15 H15 119.6 . .
C15 C16 C17 120.52(16) . .
C15 C16 H16 119.7 . .
C17 C16 H16 119.7 . .
C18 C17 C16 120.03(16) . .
C18 C17 H17 120.0 . .
C16 C17 H17 120.0 . .
C17 C18 C19 121.44(15) . .
C17 C18 H18 119.3 . .
C19 C18 H18 119.3 . .
C18 C19 C14 117.88(14) . .
C18 C19 C10 123.31(14) . .
C14 C19 C10 118.78(14) . .
C13 O3 C20 117.02(13) . .
O3 C20 H20A 109.5 . .
O3 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
O3 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O2 1.2325(19) .
C1 C2 1.445(2) .
C1 C9 1.470(2) .
C2 C3 1.342(2) .
C2 H2 0.9400 .
C3 O1 1.3636(18) .
C3 C10 1.477(2) .
O1 C4 1.3745(18) .
C4 C9 1.384(2) .
C4 C5 1.392(2) .
C5 C6 1.371(2) .
C5 H5 0.9400 .
C6 C7 1.388(3) .
C6 H6 0.9400 .
C7 C8 1.377(2) .
C7 H7 0.9400 .
C8 C9 1.403(2) .
C8 H8 0.9400 .
C10 C11 1.368(2) .
C10 C19 1.434(2) .
C11 C12 1.405(2) .
C11 H11 0.9400 .
C12 C13 1.364(2) .
C12 H12 0.9400 .
C13 O3 1.3633(18) .
C13 C14 1.429(2) .
C14 C15 1.411(2) .
C14 C19 1.420(2) .
C15 C16 1.362(2) .
C15 H15 0.9400 .
C16 C17 1.398(2) .
C16 H16 0.9400 .
C17 C18 1.366(2) .
C17 H17 0.9400 .
C18 C19 1.416(2) .
C18 H18 0.9400 .
O3 C20 1.426(2) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C20 H20C 0.9700 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O2 0.94 2.45 3.325(2) 155.7 1_455
C17 H17 O2 0.94 2.55 3.486(2) 175.1 1_445
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 -178.74(17) . . . .
C9 C1 C2 C3 0.9(2) . . . .
C1 C2 C3 O1 -0.2(2) . . . .
C1 C2 C3 C10 178.34(15) . . . .
C2 C3 O1 C4 -1.1(2) . . . .
C10 C3 O1 C4 -179.83(13) . . . .
C3 O1 C4 C9 1.7(2) . . . .
C3 O1 C4 C5 -178.72(14) . . . .
O1 C4 C5 C6 -179.19(15) . . . .
C9 C4 C5 C6 0.4(3) . . . .
C4 C5 C6 C7 -0.2(3) . . . .
C5 C6 C7 C8 -0.3(3) . . . .
C6 C7 C8 C9 0.5(3) . . . .
O1 C4 C9 C8 179.39(14) . . . .
C5 C4 C9 C8 -0.2(2) . . . .
O1 C4 C9 C1 -0.9(2) . . . .
C5 C4 C9 C1 179.50(15) . . . .
C7 C8 C9 C4 -0.3(2) . . . .
C7 C8 C9 C1 -179.96(15) . . . .
O2 C1 C9 C4 179.30(16) . . . .
C2 C1 C9 C4 -0.3(2) . . . .
O2 C1 C9 C8 -1.0(2) . . . .
C2 C1 C9 C8 179.34(15) . . . .
C2 C3 C10 C11 -51.0(2) . . . .
O1 C3 C10 C11 127.63(15) . . . .
C2 C3 C10 C19 129.10(17) . . . .
O1 C3 C10 C19 -52.22(19) . . . .
C19 C10 C11 C12 3.0(2) . . . .
C3 C10 C11 C12 -176.86(14) . . . .
C10 C11 C12 C13 -1.1(2) . . . .
C11 C12 C13 O3 177.95(14) . . . .
C11 C12 C13 C14 -2.5(2) . . . .
O3 C13 C14 C15 3.8(2) . . . .
C12 C13 C14 C15 -175.83(15) . . . .
O3 C13 C14 C19 -176.35(13) . . . .
C12 C13 C14 C19 4.1(2) . . . .
C19 C14 C15 C16 -0.7(2) . . . .
C13 C14 C15 C16 179.18(15) . . . .
C14 C15 C16 C17 0.8(3) . . . .
C15 C16 C17 C18 -0.1(3) . . . .
C16 C17 C18 C19 -0.7(3) . . . .
C17 C18 C19 C14 0.8(2) . . . .
C17 C18 C19 C10 -177.00(15) . . . .
C15 C14 C19 C18 -0.1(2) . . . .
C13 C14 C19 C18 -179.96(14) . . . .
C15 C14 C19 C10 177.79(14) . . . .
C13 C14 C19 C10 -2.1(2) . . . .
C11 C10 C19 C18 176.41(15) . . . .
C3 C10 C19 C18 -3.7(2) . . . .
C11 C10 C19 C14 -1.3(2) . . . .
C3 C10 C19 C14 178.53(13) . . . .
C12 C13 O3 C20 -9.6(2) . . . .
C14 C13 O3 C20 170.87(15) . . . .
