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#$Date: 2023-01-17 12:10:46 +0200 (Tue, 17 Jan 2023) $
#$Revision: 280377 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106482.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_8106482
loop_
_publ_author_name
'El-Sayed, Nahed N.E.'
'Almaneai, Norah M.'
'Ghabbour, Hazem A.'
'Alafeefy, Ahmed M.'
_publ_section_title
;
 Crystal structure of
 (E)-2-(4-hydroxy-3-methoxybenzylidene)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one,
 C19H18O4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              203
_journal_page_last               205
_journal_paper_doi               10.1515/ncrs-2016-0195
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C19 H18 O4'
_chemical_formula_weight         310.33
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.1472(8)
_cell_length_b                   9.7978(4)
_cell_length_c                   14.5181(6)
_cell_measurement_reflns_used    8339
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.64
_cell_measurement_theta_min      2.81
_cell_volume                     3008.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus micro tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1344
_diffrn_reflns_av_sigmaI/netI    0.0788
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            39151
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.558
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0520
_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)+(0.0310P)²+1.6400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1194
_reflns_number_gt                2466
_reflns_number_total             3461
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0195_suppl.cif
_cod_data_source_block           a_a
_cod_database_code               8106482
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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
O1 O 0.45468(6) 0.82075(12) -0.11321(9) 0.0172(3) Uani 1 1 d . . .
O2 O 0.72991(6) 1.06912(13) -0.11627(9) 0.0207(3) Uani 1 1 d . . .
O3 O 0.36151(6) 0.37388(14) 0.36125(9) 0.0197(3) Uani 1 1 d . . .
O4 O 0.28832(6) 0.58164(13) 0.31800(9) 0.0232(3) Uani 1 1 d . . .
C1 C 0.49596(9) 0.81438(17) -0.05242(12) 0.0142(4) Uani 1 1 d . . .
C2 C 0.55753(9) 0.88251(17) -0.06542(12) 0.0147(4) Uani 1 1 d . . .
C3 C 0.57352(9) 0.93631(17) -0.15192(12) 0.0155(4) Uani 1 1 d . . .
H3A H 0.5446 0.9309 -0.2000 0.019 Uiso 1 1 calc R . .
C4 C 0.63112(9) 0.99665(19) -0.16657(13) 0.0173(4) Uani 1 1 d . . .
H4A H 0.6414 1.0304 -0.2245 0.021 Uiso 1 1 calc R . .
C5 C 0.67441(9) 1.00737(18) -0.09393(13) 0.0167(4) Uani 1 1 d . . .
C6 C 0.65949(9) 0.95551(18) -0.00765(13) 0.0155(4) Uani 1 1 d . . .
H6A H 0.6882 0.9633 0.0405 0.019 Uiso 1 1 calc R . .
C7 C 0.60138(9) 0.89180(17) 0.00671(12) 0.0150(4) Uani 1 1 d . . .
C8 C 0.58494(9) 0.83213(19) 0.09932(13) 0.0179(4) Uani 1 1 d . . .
H8A H 0.5619 0.8992 0.1352 0.021 Uiso 1 1 calc R . .
H8B H 0.6235 0.8101 0.1323 0.021 Uiso 1 1 calc R . .
C9 C 0.54469(9) 0.70305(19) 0.08894(13) 0.0178(4) Uani 1 1 d . . .
H9A H 0.5692 0.6325 0.0586 0.021 Uiso 1 1 calc R . .
H9B H 0.5325 0.6697 0.1493 0.021 Uiso 1 1 calc R . .
C10 C 0.48615(9) 0.73407(17) 0.03296(13) 0.0155(4) Uani 1 1 d . . .
C11 C 0.42684(9) 0.69864(17) 0.05672(12) 0.0158(4) Uani 1 1 d . . .
H11A H 0.3943 0.7351 0.0213 0.019 Uiso 1 1 calc R . .
C12 C 0.40819(9) 0.60866(18) 0.13255(12) 0.0158(4) Uani 1 1 d . . .
C13 C 0.44199(9) 0.49039(18) 0.15217(13) 0.0180(4) Uani 1 1 d . . .
H13A H 0.4763 0.4663 0.1156 0.022 Uiso 1 1 calc R . .
C14. C 0.42482(9) 0.40813(18) 0.22580(13) 0.0168(4) Uani 1 1 d . . .
H14A H 0.4469 0.3276 0.2368 0.020 Uiso 1 1 calc R . .
C15 C 0.37567(9) 0.44399(18) 0.28277(13) 0.0154(4) Uani 1 1 d . . .
C16 C 0.33833(9) 0.55846(18) 0.26053(13) 0.0160(4) Uani 1 1 d . . .
C17 C 0.35452(9) 0.63824(18) 0.18579(13) 0.0164(4) Uani 1 1 d . . .
H17A H 0.3294 0.7128 0.1705 0.020 Uiso 1 1 calc R . .
C18 C 0.77579(10) 1.0899(2) -0.04455(14) 0.0247(5) Uani 1 1 d . . .
H18A H 0.8132 1.1303 -0.0702 0.037 Uiso 1 1 calc R . .
H18B H 0.7863 1.0037 -0.0171 0.037 Uiso 1 1 calc R . .
H18C H 0.7585 1.1494 0.0015 0.037 Uiso 1 1 calc R . .
C19 C 0.24712(10) 0.6916(2) 0.29427(15) 0.0257(5) Uani 1 1 d . . .
H19A H 0.2121 0.6937 0.3363 0.039 Uiso 1 1 calc R . .
H19B H 0.2317 0.6789 0.2327 0.039 Uiso 1 1 calc R . .
H19C H 0.2698 0.7763 0.2979 0.039 Uiso 1 1 calc R . .
H1O3 H 0.3905(12) 0.308(3) 0.3694(17) 0.049(8) 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
C5 O2 C18 118.21(15) . .
C15 O3 H1O3 108.9(16) . .
C16 O4 C19 116.78(15) . .
O1 C1 C2 120.41(16) . .
O1 C1 C10 121.47(17) . .
C2 C1 C10 118.07(15) . .
C7 C2 C3 119.00(17) . .
C7 C2 C1 121.17(16) . .
C3 C2 C1 119.81(16) . .
C4 C3 C2 121.00(17) . .
C4 C3 H3A 119.5 . .
C2 C3 H3A 119.5 . .
C3 C4 C5 119.77(18) . .
C3 C4 H4A 120.1 . .
C5 C4 H4A 120.1 . .
O2 C5 C6 125.05(17) . .
O2 C5 C4 114.71(16) . .
C6 C5 C4 120.23(17) . .
C5 C6 C7 119.95(17) . .
C5 C6 H6A 120.0 . .
C7 C6 H6A 120.0 . .
C6 C7 C2 120.03(17) . .
C6 C7 C8 120.70(16) . .
C2 C7 C8 119.27(16) . .
C7 C8 C9 111.14(15) . .
C7 C8 H8A 109.4 . .
C9 C8 H8A 109.4 . .
C7 C8 H8B 109.4 . .
C9 C8 H8B 109.4 . .
H8A C8 H8B 108.0 . .
C10 C9 C8 109.99(15) . .
C10 C9 H9A 109.7 . .
C8 C9 H9A 109.7 . .
C10 C9 H9B 109.7 . .
C8 C9 H9B 109.7 . .
H9A C9 H9B 108.2 . .
C11 C10 C1 118.77(17) . .
C11 C10 C9 124.98(17) . .
C1 C10 C9 116.20(16) . .
C10 C11 C12 126.78(17) . .
C10 C11 H11A 116.6 . .
C12 C11 H11A 116.6 . .
C13 C12 C17 118.35(17) . .
C13 C12 C11 121.13(17) . .
C17 C12 C11 120.50(16) . .
C14. C13 C12 120.49(18) . .
C14. C13 H13A 119.8 . .
C12 C13 H13A 119.8 . .
C15 C14. C13 120.88(17) . .
C15 C14. H14A 119.6 . .
C13 C14. H14A 119.6 . .
O3 C15 C14. 122.70(17) . .
O3 C15 C16 117.99(17) . .
C14. C15 C16 119.31(17) . .
O4 C16 C17 125.31(17) . .
O4 C16 C15 115.23(16) . .
C17 C16 C15 119.45(17) . .
C16 C17 C12 121.10(17) . .
C16 C17 H17A 119.4 . .
C12 C17 H17A 119.4 . .
O2 C18 H18A 109.5 . .
O2 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
O2 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
O4 C19 H19A 109.5 . .
O4 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
O4 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.243(2) .
O2 C5 1.360(2) .
O2 C18 1.438(2) .
O3 C15 1.364(2) .
O3 H1O3 0.90(3) .
O4 C16 1.366(2) .
O4 C19 1.428(2) .
C1 C2 1.475(3) .
C1 C10 1.483(3) .
C2 C7 1.402(3) .
C2 C3 1.403(3) .
C3 C4 1.371(3) .
C3 H3A 0.9300 .
C4 C5 1.400(3) .
C4 H4A 0.9300 .
C5 C6 1.388(3) .
C6 C7 1.394(3) .
C6 H6A 0.9300 .
C7 C8 1.507(3) .
C8 C9 1.532(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.512(3) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.346(3) .
C11 C12 1.464(3) .
C11 H11A 0.9300 .
C12 C13 1.391(3) .
C12 C17 1.403(3) .
C13 C14. 1.387(3) .
C13 H13A 0.9300 .
C14. C15 1.374(3) .
C14. H14A 0.9300 .
C15 C16 1.409(3) .
C16 C17 1.380(3) .
C17 H17A 0.9300 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C1 C2 C7 171.52(16) . . . .
C10 C1 C2 C7 -11.0(2) . . . .
O1 C1 C2 C3 -10.1(3) . . . .
C10 C1 C2 C3 167.41(16) . . . .
C7 C2 C3 C4 0.3(3) . . . .
C1 C2 C3 C4 -178.13(16) . . . .
C2 C3 C4 C5 -1.2(3) . . . .
C18 O2 C5 C6 -3.7(3) . . . .
C18 O2 C5 C4 177.17(16) . . . .
C3 C4 C5 O2 -179.92(16) . . . .
C3 C4 C5 C6 0.9(3) . . . .
O2 C5 C6 C7 -178.75(16) . . . .
C4 C5 C6 C7 0.4(3) . . . .
C5 C6 C7 C2 -1.3(3) . . . .
C5 C6 C7 C8 178.63(17) . . . .
C3 C2 C7 C6 0.9(3) . . . .
C1 C2 C7 C6 179.35(16) . . . .
C3 C2 C7 C8 -178.98(16) . . . .
C1 C2 C7 C8 -0.6(3) . . . .
C6 C7 C8 C9 -145.47(17) . . . .
C2 C7 C8 C9 34.4(2) . . . .
C7 C8 C9 C10 -55.8(2) . . . .
O1 C1 C10 C11 -18.1(3) . . . .
C2 C1 C10 C11 164.45(16) . . . .
O1 C1 C10 C9 164.23(16) . . . .
C2 C1 C10 C9 -13.2(2) . . . .
C8 C9 C10 C11 -131.41(19) . . . .
C8 C9 C10 C1 46.1(2) . . . .
C1 C10 C11 C12 173.35(16) . . . .
C9 C10 C11 C12 -9.2(3) . . . .
C10 C11 C12 C13 -40.5(3) . . . .
C10 C11 C12 C17 141.14(19) . . . .
C17 C12 C13 C14. -3.5(3) . . . .
C11 C12 C13 C14. 178.20(17) . . . .
C12 C13 C14. C15 -2.3(3) . . . .
C13 C14. C15 O3 -172.93(16) . . . .
C13 C14. C15 C16 6.4(3) . . . .
C19 O4 C16 C17 4.8(3) . . . .
C19 O4 C16 C15 -176.18(16) . . . .
O3 C15 C16 O4 -4.3(2) . . . .
C14. C15 C16 O4 176.28(16) . . . .
O3 C15 C16 C17 174.72(16) . . . .
C14. C15 C16 C17 -4.7(3) . . . .
O4 C16 C17 C12 177.80(17) . . . .
C15 C16 C17 C12 -1.1(3) . . . .
C13 C12 C17 C16 5.2(3) . . . .
C11 C12 C17 C16 -176.47(17) . . . .
