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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/40/4504002.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_4504002
loop_
_publ_author_name
'Mori, Yutaka'
'Matsumoto, Akikazu'
_publ_section_title
;
 Molecular Stacking and Photoreactions of Fluorine-Substituted Benzyl
 Muconates in the Crystals
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              377
_journal_paper_doi               10.1021/cg060643b
_journal_volume                  7
_journal_year                    2007
_chemical_formula_moiety         'C20 H10 F8 O4 '
_chemical_formula_sum            'C20 H10 F8 O4'
_chemical_formula_weight         466.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 104.50(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.483(5)
_cell_length_b                   7.009(3)
_cell_length_c                   11.849(5)
_cell_measurement_reflns_used    7883
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.4
_cell_volume                     923.3(7)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      203(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2076
_diffrn_reflns_theta_full        27.38
_diffrn_reflns_theta_max         27.38
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.9752
_exptl_absorpt_correction_T_min  0.9130
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0686
_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)+(0.1216P)²+0.4069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1843
_refine_ls_wR_factor_ref         0.2056
_reflns_number_gt                1413
_reflns_number_total             2076
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060643bsi20060925_060206.cif
_cod_data_source_block           (Z,Z)-5
_cod_original_cell_volume        923.3(6)
_cod_database_code               4504002
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F6 F -0.20983(18) 0.0722(2) 0.24498(15) 0.0573(5) Uani 1 1 d .
F7 F -0.3391(2) -0.2368(3) 0.1570(2) 0.0686(6) Uani 1 1 d .
F8 F -0.4455(2) -0.2607(3) -0.0745(2) 0.0774(7) Uani 1 1 d .
F9 F -0.4283(2) 0.0363(3) -0.21612(18) 0.0754(7) Uani 1 1 d .
O1 O -0.0588(2) 0.7146(3) 0.15758(17) 0.0502(6) Uani 1 1 d .
O2 O -0.1614(2) 0.5099(3) 0.02347(16) 0.0466(5) Uani 1 1 d .
C1 C -0.0970(2) 0.6714(4) 0.0569(2) 0.0382(6) Uani 1 1 d .
C2 C -0.0855(3) 0.7760(4) -0.0477(2) 0.0420(6) Uani 1 1 d .
H2 H -0.1205 0.7191 -0.1201 0.050 Uiso 1 1 calc R
C3 C -0.0306(3) 0.9428(4) -0.0503(2) 0.0415(6) Uani 1 1 d .
H3 H -0.0312 0.9919 -0.1243 0.050 Uiso 1 1 calc R
C4 C -0.1814(3) 0.3915(4) 0.1158(2) 0.0434(7) Uani 1 1 d .
H4A H -0.2256 0.4626 0.1629 0.052 Uiso 1 1 calc R
H4B H -0.1044 0.3504 0.1665 0.052 Uiso 1 1 calc R
C5 C -0.2531(3) 0.2210(4) 0.0609(2) 0.0402(6) Uani 1 1 d .
C6 C -0.2639(3) 0.0675(4) 0.1304(2) 0.0429(7) Uani 1 1 d .
C7 C -0.3291(3) -0.0929(4) 0.0862(3) 0.0486(7) Uani 1 1 d .
C8 C -0.3837(3) -0.1042(4) -0.0313(3) 0.0536(8) Uani 1 1 d .
C9 C -0.3734(3) 0.0483(5) -0.1014(3) 0.0517(7) Uani 1 1 d .
C10 C -0.3104(3) 0.2098(4) -0.0568(2) 0.0462(7) Uani 1 1 d .
H10 H -0.3062 0.3130 -0.1064 0.055 Uiso 1 1 calc R
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'
F F 0.0171 0.0103 '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
C1 O2 C4 116.1(2) . .
O1 C1 O2 122.5(2) . .
O1 C1 C2 128.5(3) . .
O2 C1 C2 109.1(2) . .
C3 C2 C1 126.7(3) . .
C3 C2 H2 116.6 . .
C1 C2 H2 116.6 . .
C2 C3 C3 126.6(3) . 3_575
C2 C3 H3 116.7 . .
C3 C3 H3 116.7 3_575 .
O2 C4 C5 107.8(2) . .
O2 C4 H4A 110.2 . .
C5 C4 H4A 110.2 . .
O2 C4 H4B 110.2 . .
C5 C4 H4B 110.2 . .
H4A C4 H4B 108.5 . .
C6 C5 C10 117.7(3) . .
C6 C5 C4 118.9(3) . .
C10 C5 C4 123.4(2) . .
F6 C6 C7 118.2(2) . .
F6 C6 C5 119.7(3) . .
C7 C6 C5 122.1(3) . .
F7 C7 C8 120.1(3) . .
F7 C7 C6 120.1(3) . .
C8 C7 C6 119.8(3) . .
F8 C8 C9 121.5(3) . .
F8 C8 C7 119.9(3) . .
C9 C8 C7 118.6(3) . .
F9 C9 C10 120.4(3) . .
F9 C9 C8 118.1(3) . .
C10 C9 C8 121.6(3) . .
C9 C10 C5 120.2(3) . .
C9 C10 H10 119.9 . .
C5 C10 H10 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F6 C6 1.345(3) .
F7 C7 1.335(3) .
F8 C8 1.337(4) .
F9 C9 1.350(4) .
O1 C1 1.202(3) .
O2 C1 1.356(3) .
O2 C4 1.437(3) .
C1 C2 1.474(4) .
C2 C3 1.332(4) .
C2 H2 0.9400 .
C3 C3 1.462(6) 3_575
C3 H3 0.9400 .
C4 C5 1.503(4) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C5 C6 1.379(4) .
C5 C10 1.388(4) .
C6 C7 1.379(4) .
C7 C8 1.378(5) .
C8 C9 1.377(5) .
C9 C10 1.376(4) .
C10 H10 0.9400 .
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_4
C4 O2 C1 O1 -0.2(4) .
C4 O2 C1 C2 -179.7(2) .
O1 C1 C2 C3 -0.9(5) .
O2 C1 C2 C3 178.5(3) .
C1 C2 C3 C3 0.4(6) 3_575
C1 O2 C4 C5 -179.7(2) .
O2 C4 C5 C6 167.3(2) .
O2 C4 C5 C10 -13.2(4) .
C10 C5 C6 F6 180.0(2) .
C4 C5 C6 F6 -0.5(4) .
C10 C5 C6 C7 -0.1(4) .
C4 C5 C6 C7 179.5(3) .
F6 C6 C7 F7 1.2(4) .
C5 C6 C7 F7 -178.8(3) .
F6 C6 C7 C8 -178.7(3) .
C5 C6 C7 C8 1.4(4) .
F7 C7 C8 F8 -0.8(4) .
C6 C7 C8 F8 179.1(3) .
F7 C7 C8 C9 178.8(3) .
C6 C7 C8 C9 -1.3(5) .
F8 C8 C9 F9 0.3(5) .
C7 C8 C9 F9 -179.3(3) .
F8 C8 C9 C10 179.6(3) .
C7 C8 C9 C10 0.0(5) .
F9 C9 C10 C5 -179.4(3) .
C8 C9 C10 C5 1.3(5) .
C6 C5 C10 C9 -1.2(4) .
C4 C5 C10 C9 179.2(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102275443
