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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/26/1502695.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_1502695
loop_
_publ_author_name
'Balomenou, Ioanna'
'Kaloudi-Chantzea, Antonia'
'Bokias, Georgios'
'Kallitsis, Joannis K.'
'Raptopoulou, Catherine P.'
'Terzis, Aris'
'Pistolis, George'
_publ_section_title
;
 Medium effect on the geometric isomerism of a centrosymmetrically
 disubstituted naphthalene derivative with flexible methoxytriethylene
 glycol chains.
;
_journal_issue                   24
_journal_name_full               'The journal of physical chemistry. B'
_journal_page_first              8181
_journal_page_last               8190
_journal_paper_doi               10.1021/jp103095z
_journal_volume                  114
_journal_year                    2010
_chemical_formula_sum            'C24 H36 O8'
_chemical_formula_weight         452.53
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.1297(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6041(2)
_cell_length_b                   7.88330(10)
_cell_length_c                   18.1199(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1205.93(4)
_computing_cell_refinement       'CrystalClear, Rigaku MSC, 2005'
_computing_data_collection       'CrystalClear, Rigaku MSC, 2005'
_computing_data_reduction        'CrystalClear, Rigaku MSC, 2005'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IPDS'
_diffrn_measurement_method       'θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8010
_diffrn_reflns_theta_full        67.98
_diffrn_reflns_theta_max         67.98
_diffrn_reflns_theta_min         7.47
_diffrn_standards_decay_%        -0.9
_exptl_absorpt_coefficient_mu    0.765
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parall
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0038(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0579
_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+0.5915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1666
_refine_ls_wR_factor_ref         0.1718
_reflns_number_gt                1818
_reflns_number_total             2087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp103095z_si_001.cif
_cod_data_source_block           npeg
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               1502695
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, z'
'-x, -y, -z'
'-x-1/2, y-1/2, -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
O1 O 0.61486(16) 0.0223(2) 0.84787(8) 0.0482(4) Uani 1 1 d .
O2 O 0.29198(16) -0.0536(2) 0.78249(8) 0.0504(5) Uani 1 1 d .
O3 O 0.18942(19) -0.3185(2) 0.67154(9) 0.0640(5) Uani 1 1 d .
C1 C 0.9397(2) 0.0404(2) 1.01529(10) 0.0382(5) Uani 1 1 d .
C2 C 0.7868(2) 0.0623(3) 0.97024(11) 0.0411(5) Uani 1 1 d .
C3 C 0.7558(2) 0.0059(3) 0.89715(11) 0.0397(5) Uani 1 1 d .
C4 C 0.8761(2) -0.0755(3) 0.86674(12) 0.0454(5) Uani 1 1 d .
C5 C 1.0230(2) -0.0971(3) 0.90911(11) 0.0463(5) Uani 1 1 d .
C6 C 0.4825(3) 0.0878(3) 0.87543(13) 0.0510(6) Uani 1 1 d .
H6A H 0.506(3) 0.201(4) 0.8996(14) 0.059(7) Uiso 1 1 d .
H6B H 0.454(3) 0.008(3) 0.9134(15) 0.059(7) Uiso 1 1 d .
C7 C 0.3482(3) 0.1068(3) 0.80984(15) 0.0568(6) Uani 1 1 d .
H7A H 0.266(3) 0.169(4) 0.8258(16) 0.075(8) Uiso 1 1 d .
H7B H 0.390(3) 0.173(4) 0.7656(16) 0.075(8) Uiso 1 1 d .
C8 C 0.1675(3) -0.0405(4) 0.71927(14) 0.0604(7) Uani 1 1 d .
H8A H 0.212(3) 0.014(4) 0.6785(17) 0.070(8) Uiso 1 1 d .
H8B H 0.091(4) 0.044(4) 0.7315(18) 0.084(9) Uiso 1 1 d .
C9 C 0.0884(3) -0.2073(4) 0.70045(15) 0.0639(7) Uani 1 1 d .
H9A H 0.056(3) -0.259(4) 0.7461(17) 0.080(8) Uiso 1 1 d .
H9B H -0.007(3) -0.189(4) 0.6619(17) 0.077(8) Uiso 1 1 d .
C10 C 0.1147(5) -0.4744(5) 0.6495(2) 0.0927(12) Uani 1 1 d .
H10A H 0.023(6) -0.447(6) 0.605(3) 0.149(18) Uiso 1 1 d .
H10B H 0.066(5) -0.521(6) 0.685(3) 0.133(16) Uiso 1 1 d .
C11 C 0.2182(6) -0.5910(5) 0.6182(2) 0.1189(15) Uani 1 1 d .
H11A H 0.3155 -0.6067 0.6548 0.143 Uiso 1 1 calc R
H11B H 0.1665 -0.7005 0.6097 0.143 Uiso 1 1 calc R
O4 O 0.2531(7) -0.5377(5) 0.5554(2) 0.203(2) Uani 1 1 d .
C12 C 0.3146(8) -0.6403(8) 0.5109(3) 0.171(2) Uani 1 1 d .
H12A H 0.3207 -0.5824 0.4650 0.222 Uiso 1 1 calc R
H12B H 0.2488 -0.7389 0.4999 0.222 Uiso 1 1 calc R
H12C H 0.4189 -0.6740 0.5356 0.222 Uiso 1 1 calc R
H2 H 0.710(3) 0.123(3) 0.9927(13) 0.047(6) Uiso 1 1 d .
H4 H 0.848(3) -0.118(3) 0.8177(15) 0.056(7) Uiso 1 1 d .
H5 H 1.106(3) -0.158(3) 0.8885(13) 0.051(6) 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 0.0181 0.0091 '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 0.0492 0.0322 '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
C3 O1 C6 118.28(15) . .
C7 O2 C8 111.96(19) . .
C9 O3 C10 111.6(2) . .
C5 C1 C2 121.98(18) 3_757 .
C5 C1 C1 118.2(2) 3_757 3_757
C2 C1 C1 119.8(2) . 3_757
C3 C2 C1 120.11(18) . .
C3 C2 H2 123.0(13) . .
C1 C2 H2 116.8(13) . .
O1 C3 C2 125.61(18) . .
O1 C3 C4 114.31(17) . .
C2 C3 C4 120.07(19) . .
C5 C4 C3 120.52(19) . .
C5 C4 H4 122.3(14) . .
C3 C4 H4 117.2(15) . .
C4 C5 C1 121.28(19) . 3_757
C4 C5 H5 120.5(13) . .
C1 C5 H5 118.2(13) 3_757 .
O1 C6 C7 107.76(19) . .
O1 C6 H6A 111.7(14) . .
C7 C6 H6A 108.6(15) . .
O1 C6 H6B 109.3(15) . .
C7 C6 H6B 110.8(15) . .
H6A C6 H6B 109(2) . .
O2 C7 C6 110.4(2) . .
O2 C7 H7A 110.5(18) . .
C6 C7 H7A 108.3(17) . .
O2 C7 H7B 108.4(15) . .
C6 C7 H7B 108.9(15) . .
H7A C7 H7B 110(2) . .
O2 C8 C9 111.2(2) . .
O2 C8 H8A 107.1(16) . .
C9 C8 H8A 115.9(17) . .
O2 C8 H8B 107.5(18) . .
C9 C8 H8B 110.5(19) . .
H8A C8 H8B 104(2) . .
O3 C9 C8 110.3(2) . .
O3 C9 H9A 110.1(18) . .
C8 C9 H9A 110.9(18) . .
O3 C9 H9B 108.6(17) . .
C8 C9 H9B 108.3(17) . .
H9A C9 H9B 109(2) . .
O3 C10 C11 112.2(3) . .
O3 C10 H10A 106(3) . .
C11 C10 H10A 105(3) . .
O3 C10 H10B 113(3) . .
C11 C10 H10B 115(3) . .
H10A C10 H10B 104(4) . .
O4 C11 C10 113.3(4) . .
O4 C11 H11A 108.9 . .
C10 C11 H11A 108.9 . .
O4 C11 H11B 108.9 . .
C10 C11 H11B 108.9 . .
H11A C11 H11B 107.7 . .
C11 O4 C12 121.5(5) . .
O4 C12 H12A 109.5 . .
O4 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
O4 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.366(2) .
O1 C6 1.426(2) .
O2 C7 1.410(3) .
O2 C8 1.413(3) .
O3 C9 1.405(3) .
O3 C10 1.409(4) .
C1 C5 1.418(3) 3_757
C1 C2 1.418(3) .
C1 C1 1.418(4) 3_757
C2 C3 1.373(3) .
C2 H2 0.96(2) .
C3 C4 1.416(3) .
C4 C5 1.357(3) .
C4 H4 0.94(3) .
C5 C1 1.418(3) 3_757
C5 H5 0.99(2) .
C6 C7 1.497(3) .
C6 H6A 1.00(3) .
C6 H6B 1.00(3) .
C7 H7A 0.95(3) .
C7 H7B 1.07(3) .
C8 C9 1.490(4) .
C8 H8A 0.99(3) .
C8 H8B 0.99(3) .
C9 H9A 1.01(3) .
C9 H9B 0.98(3) .
C10 C11 1.467(6) .
C10 H10A 1.03(5) .
C10 H10B 0.91(5) .
C11 O4 1.301(5) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
O4 C12 1.323(5) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 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_4
C5 C1 C2 C3 179.8(2) 3_757 .
C1 C1 C2 C3 -0.2(3) 3_757 .
C6 O1 C3 C2 -6.7(3) . .
C6 O1 C3 C4 174.1(2) . .
C1 C2 C3 O1 -178.70(18) . .
C1 C2 C3 C4 0.5(3) . .
O1 C3 C4 C5 178.69(19) . .
C2 C3 C4 C5 -0.6(3) . .
C3 C4 C5 C1 0.3(3) . 3_757
C3 O1 C6 C7 175.29(19) . .
C8 O2 C7 C6 -178.5(2) . .
O1 C6 C7 O2 69.6(3) . .
C7 O2 C8 C9 -168.7(2) . .
C10 O3 C9 C8 -176.8(3) . .
O2 C8 C9 O3 -70.2(3) . .
C9 O3 C10 C11 179.3(3) . .
O3 C10 C11 O4 -65.5(6) . .
C10 C11 O4 C12 -164.8(5) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102508214
