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#$Date: 2023-06-09 09:56:21 +0300 (Fri, 09 Jun 2023) $
#$Revision: 284425 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107330.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_8107330
loop_
_publ_author_name
'Shin, Soon Young'
'Ahn, Seunghyun'
'Koh, Dongsoo'
_publ_section_title
;
 The crystal structure of
 (Z)-2-(2,3-dimethoxybenzylidene)naphtho[1,2-b]furan-3(2H)-one, C21H16O4
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1189
_journal_page_last               1191
_journal_paper_doi               10.1515/ncrs-2022-0454
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C21 H16 O4'
_chemical_formula_sum            'C21 H16 O4'
_chemical_formula_weight         332.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.322(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.531(6)
_cell_length_b                   8.390(3)
_cell_length_c                   14.288(5)
_cell_measurement_reflns_used    6783
_cell_measurement_temperature    243(2)
_cell_measurement_theta_max      27.76
_cell_measurement_theta_min      2.18
_cell_volume                     1615.1(11)
_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      243(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'PHOTON III M14'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1039
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22301
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.286
_diffrn_reflns_theta_min         2.176
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.121
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0588
_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)+(0.0920P)²+0.3816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1795
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2950
_reflns_number_total             3996
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0454_suppl.cif
_cod_data_source_block           DK3610
_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_sg_symbol_H-M      'P 21/n'
_cod_database_code               8107330
_shelx_shelxl_version_number     2014/7
_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   0.968
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_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 0.44741(14) 0.1623(2) 0.46621(12) 0.0357(4) Uani 1 1 d . . . . .
C2 C 0.50026(13) 0.2727(2) 0.53500(12) 0.0344(4) Uani 1 1 d . . . . .
C3 C 0.34777(12) 0.24218(19) 0.57697(12) 0.0329(4) Uani 1 1 d . . . . .
C4 C 0.34783(13) 0.1507(2) 0.49765(12) 0.0350(4) Uani 1 1 d . . . . .
C5 C 0.26188(15) 0.0662(2) 0.46344(14) 0.0445(5) Uani 1 1 d . . . . .
H5 H 0.2612 0.0039 0.4087 0.053 Uiso 1 1 calc R U . . .
C6 C 0.18013(15) 0.0771(2) 0.51164(15) 0.0477(5) Uani 1 1 d . . . . .
H6 H 0.1222 0.0221 0.4891 0.057 Uiso 1 1 calc R U . . .
C7 C 0.17957(14) 0.1695(2) 0.59558(14) 0.0398(4) Uani 1 1 d . . . . .
C8 C 0.26597(12) 0.25499(19) 0.63075(12) 0.0348(4) Uani 1 1 d . . . . .
C9 C 0.26689(14) 0.3431(2) 0.71501(14) 0.0407(4) Uani 1 1 d . . . . .
H9 H 0.3244 0.3986 0.7382 0.049 Uiso 1 1 calc R U . . .
C10 C 0.18381(16) 0.3475(2) 0.76279(16) 0.0482(5) Uani 1 1 d . . . . .
H10 H 0.1846 0.4054 0.8192 0.058 Uiso 1 1 calc R U . . .
C11 C 0.09771(16) 0.2661(3) 0.72817(17) 0.0514(5) Uani 1 1 d . . . . .
H11 H 0.0408 0.2708 0.7612 0.062 Uiso 1 1 calc R U . . .
C12 C 0.09554(15) 0.1800(3) 0.64707(17) 0.0488(5) Uani 1 1 d . . . . .
H12 H 0.0369 0.1265 0.6250 0.059 Uiso 1 1 calc R U . . .
C13 C 0.59487(13) 0.3185(2) 0.53678(13) 0.0357(4) Uani 1 1 d . . . . .
H13 H 0.6303 0.2741 0.4895 0.043 Uiso 1 1 calc R U . . .
C14 C 0.65183(13) 0.42726(19) 0.60096(12) 0.0332(4) Uani 1 1 d . . . . .
C15 C 0.75494(13) 0.4328(2) 0.59891(12) 0.0346(4) Uani 1 1 d . . . . .
C16 C 0.81202(13) 0.5389(2) 0.65694(12) 0.0364(4) Uani 1 1 d . . . . .
C17 C 0.76600(14) 0.6373(2) 0.71726(14) 0.0419(4) Uani 1 1 d . . . . .
H17 H 0.8039 0.7099 0.7557 0.050 Uiso 1 1 calc R U . . .
C18 C 0.66408(14) 0.6294(2) 0.72118(13) 0.0419(4) Uani 1 1 d . . . . .
H18 H 0.6336 0.6955 0.7631 0.050 Uiso 1 1 calc R U . . .
C19 C 0.60726(13) 0.5258(2) 0.66439(13) 0.0373(4) Uani 1 1 d . . . . .
H19 H 0.5383 0.5209 0.6681 0.045 Uiso 1 1 calc R U . . .
C20 C 0.85538(19) 0.3787(3) 0.47303(16) 0.0585(6) Uani 1 1 d . . . . .
H20A H 0.8207 0.4667 0.4404 0.088 Uiso 1 1 calc R U . . .
H20B H 0.8642 0.2932 0.4289 0.088 Uiso 1 1 calc R U . . .
H20C H 0.9198 0.4148 0.5005 0.088 Uiso 1 1 calc R U . . .
C21 C 0.97169(15) 0.6384(3) 0.70991(15) 0.0494(5) Uani 1 1 d . . . . .
H21A H 0.9539 0.7478 0.6942 0.074 Uiso 1 1 calc R U . . .
H21B H 1.0411 0.6213 0.7011 0.074 Uiso 1 1 calc R U . . .
H21C H 0.9608 0.6179 0.7750 0.074 Uiso 1 1 calc R U . . .
O1 O 0.48285(10) 0.09806(16) 0.40039(9) 0.0452(4) Uani 1 1 d . . . . .
O2 O 0.43599(9) 0.31936(14) 0.60111(9) 0.0366(3) Uani 1 1 d . . . . .
O3 O 0.79900(10) 0.32251(15) 0.54507(10) 0.0434(3) Uani 1 1 d . . . . .
O4 O 0.91200(10) 0.53332(18) 0.65050(10) 0.0480(4) Uani 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
O1 C1 C4 130.27(17) . .
O1 C1 C2 125.90(17) . .
C4 C1 C2 103.83(15) . .
C13 C2 O2 124.21(16) . .
C13 C2 C1 126.47(16) . .
O2 C2 C1 109.29(15) . .
C4 C3 O2 113.89(15) . .
C4 C3 C8 123.72(16) . .
O2 C3 C8 122.38(15) . .
C3 C4 C5 120.34(17) . .
C3 C4 C1 106.76(16) . .
C5 C4 C1 132.89(17) . .
C6 C5 C4 118.32(18) . .
C6 C5 H5 120.8 . .
C4 C5 H5 120.8 . .
C5 C6 C7 121.98(18) . .
C5 C6 H6 119.0 . .
C7 C6 H6 119.0 . .
C12 C7 C8 117.34(18) . .
C12 C7 C6 122.54(18) . .
C8 C7 C6 120.12(17) . .
C3 C8 C9 124.04(16) . .
C3 C8 C7 115.49(16) . .
C9 C8 C7 120.46(16) . .
C10 C9 C8 119.78(18) . .
C10 C9 H9 120.1 . .
C8 C9 H9 120.1 . .
C9 C10 C11 120.4(2) . .
C9 C10 H10 119.8 . .
C11 C10 H10 119.8 . .
C12 C11 C10 120.67(19) . .
C12 C11 H11 119.7 . .
C10 C11 H11 119.7 . .
C11 C12 C7 121.36(19) . .
C11 C12 H12 119.3 . .
C7 C12 H12 119.3 . .
C2 C13 C14 129.85(17) . .
C2 C13 H13 115.1 . .
C14 C13 H13 115.1 . .
C15 C14 C19 118.89(16) . .
C15 C14 C13 118.45(15) . .
C19 C14 C13 122.65(16) . .
O3 C15 C14 118.34(16) . .
O3 C15 C16 121.05(16) . .
C14 C15 C16 120.36(16) . .
O4 C16 C17 124.67(17) . .
O4 C16 C15 115.74(16) . .
C17 C16 C15 119.57(17) . .
C16 C17 C18 120.22(17) . .
C16 C17 H17 119.9 . .
C18 C17 H17 119.9 . .
C19 C18 C17 120.69(17) . .
C19 C18 H18 119.7 . .
C17 C18 H18 119.7 . .
C18 C19 C14 120.21(17) . .
C18 C19 H19 119.9 . .
C14 C19 H19 119.9 . .
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 . .
O4 C21 H21A 109.5 . .
O4 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
O4 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C3 O2 C2 106.20(13) . .
C15 O3 C20 118.23(15) . .
C16 O4 C21 116.74(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.220(2) .
C1 C4 1.463(3) .
C1 C2 1.485(3) .
C2 C13 1.335(2) .
C2 O2 1.398(2) .
C3 C4 1.369(2) .
C3 O2 1.374(2) .
C3 C8 1.409(2) .
C4 C5 1.410(3) .
C5 C6 1.359(3) .
C5 H5 0.9400 .
C6 C7 1.429(3) .
C6 H6 0.9400 .
C7 C12 1.413(3) .
C7 C8 1.423(3) .
C8 C9 1.412(3) .
C9 C10 1.369(3) .
C9 H9 0.9400 .
C10 C11 1.400(3) .
C10 H10 0.9400 .
C11 C12 1.363(3) .
C11 H11 0.9400 .
C12 H12 0.9400 .
C13 C14 1.461(2) .
C13 H13 0.9400 .
C14 C15 1.399(2) .
C14 C19 1.403(2) .
C15 O3 1.374(2) .
C15 C16 1.399(3) .
C16 O4 1.365(2) .
C16 C17 1.383(3) .
C17 C18 1.387(3) .
C17 H17 0.9400 .
C18 C19 1.374(3) .
C18 H18 0.9400 .
C19 H19 0.9400 .
C20 O3 1.418(2) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C20 H20C 0.9700 .
C21 O4 1.423(2) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C21 H21C 0.9700 .
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
O1 C1 C2 C13 -0.6(3) . . . .
C4 C1 C2 C13 178.68(17) . . . .
O1 C1 C2 O2 -178.83(16) . . . .
C4 C1 C2 O2 0.49(18) . . . .
O2 C3 C4 C5 -179.07(15) . . . .
C8 C3 C4 C5 2.0(3) . . . .
O2 C3 C4 C1 2.1(2) . . . .
C8 C3 C4 C1 -176.78(16) . . . .
O1 C1 C4 C3 177.78(18) . . . .
C2 C1 C4 C3 -1.49(18) . . . .
O1 C1 C4 C5 -0.8(3) . . . .
C2 C1 C4 C5 179.90(19) . . . .
C3 C4 C5 C6 -0.6(3) . . . .
C1 C4 C5 C6 177.87(19) . . . .
C4 C5 C6 C7 -0.7(3) . . . .
C5 C6 C7 C12 -179.1(2) . . . .
C5 C6 C7 C8 0.6(3) . . . .
C4 C3 C8 C9 176.93(17) . . . .
O2 C3 C8 C9 -1.9(3) . . . .
C4 C3 C8 C7 -2.1(3) . . . .
O2 C3 C8 C7 179.14(15) . . . .
C12 C7 C8 C3 -179.59(17) . . . .
C6 C7 C8 C3 0.8(3) . . . .
C12 C7 C8 C9 1.4(3) . . . .
C6 C7 C8 C9 -178.27(17) . . . .
C3 C8 C9 C10 -179.49(18) . . . .
C7 C8 C9 C10 -0.5(3) . . . .
C8 C9 C10 C11 -0.5(3) . . . .
C9 C10 C11 C12 0.7(3) . . . .
C10 C11 C12 C7 0.2(3) . . . .
C8 C7 C12 C11 -1.2(3) . . . .
C6 C7 C12 C11 178.4(2) . . . .
O2 C2 C13 C14 -2.8(3) . . . .
C1 C2 C13 C14 179.27(16) . . . .
C2 C13 C14 C15 168.13(18) . . . .
C2 C13 C14 C19 -11.8(3) . . . .
C19 C14 C15 O3 172.17(15) . . . .
C13 C14 C15 O3 -7.8(2) . . . .
C19 C14 C15 C16 -2.2(2) . . . .
C13 C14 C15 C16 177.89(16) . . . .
O3 C15 C16 O4 4.9(2) . . . .
C14 C15 C16 O4 179.13(15) . . . .
O3 C15 C16 C17 -173.49(16) . . . .
C14 C15 C16 C17 0.7(3) . . . .
O4 C16 C17 C18 -177.37(18) . . . .
C15 C16 C17 C18 0.9(3) . . . .
C16 C17 C18 C19 -1.0(3) . . . .
C17 C18 C19 C14 -0.5(3) . . . .
C15 C14 C19 C18 2.1(3) . . . .
C13 C14 C19 C18 -178.00(16) . . . .
C4 C3 O2 C2 -1.78(19) . . . .
C8 C3 O2 C2 177.12(16) . . . .
C13 C2 O2 C3 -177.55(17) . . . .
C1 C2 O2 C3 0.70(17) . . . .
C14 C15 O3 C20 121.6(2) . . . .
C16 C15 O3 C20 -64.1(2) . . . .
C17 C16 O4 C21 -0.7(3) . . . .
C15 C16 O4 C21 -179.07(16) . . . .
