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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/4/50/39/4503996.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_4503996
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           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.484(16)
_cell_angle_beta                 97.572(18)
_cell_angle_gamma                104.33(2)
_cell_formula_units_Z            1
_cell_length_a                   5.128(2)
_cell_length_b                   5.4881(17)
_cell_length_c                   17.557(6)
_cell_measurement_reflns_used    3708
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      3.5
_cell_volume                     472.3(3)
_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 0.928
_diffrn_measured_fraction_theta_max 0.928
_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    0.0080
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            1998
_diffrn_reflns_theta_full        27.38
_diffrn_reflns_theta_max         27.38
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  0.9600
_exptl_absorpt_correction_T_min  0.9076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             234
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0679
_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)+(0.1327P)²+0.0893P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1969
_refine_ls_wR_factor_ref         0.2108
_reflns_number_gt                1559
_reflns_number_total             1998
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060643bsi20060925_055641.cif
_cod_data_source_block           (E,E)-7
_cod_database_code               4503996
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F6 F -0.2144(4) 0.7747(4) 0.23519(12) 0.0965(6) Uani 1 1 d .
F7 F -0.3997(5) 0.6381(6) 0.08529(15) 0.1460(12) Uani 1 1 d .
F9 F 0.1499(6) 0.0601(5) 0.08421(13) 0.1422(11) Uani 1 1 d .
F10 F 0.3343(4) 0.2019(4) 0.23427(12) 0.0913(6) Uani 1 1 d .
O1 O -0.2289(3) 0.5538(3) 0.40868(10) 0.0622(5) Uani 1 1 d .
O2 O 0.0647(3) 0.3540(3) 0.36592(8) 0.0573(5) Uani 1 1 d .
C1 C -0.1422(4) 0.3693(4) 0.40419(11) 0.0468(5) Uani 1 1 d .
C2 C -0.2464(4) 0.1347(4) 0.43934(11) 0.0492(5) Uani 1 1 d .
H2 H -0.1705 -0.0025 0.4315 0.059 Uiso 1 1 calc R
C3 C -0.4457(4) 0.1129(4) 0.48193(11) 0.0484(5) Uani 1 1 d .
H3 H -0.5199 0.2516 0.4889 0.058 Uiso 1 1 calc R
C4 C 0.1727(5) 0.5657(4) 0.32356(12) 0.0570(5) Uani 1 1 d .
H4A H 0.3722 0.6076 0.3321 0.068 Uiso 1 1 calc R
H4B H 0.1158 0.7142 0.3415 0.068 Uiso 1 1 calc R
C5 C 0.0661(5) 0.4931(5) 0.23885(13) 0.0625(6) Uani 1 1 d .
C6 C -0.1215(6) 0.5990(6) 0.19885(16) 0.0766(8) Uani 1 1 d .
C7 C -0.2172(7) 0.5268(9) 0.1212(2) 0.1043(13) Uani 1 1 d .
C8 C -0.1299(9) 0.3438(9) 0.0817(2) 0.1156(16) Uani 1 1 d .
H8 H -0.1976 0.2932 0.0292 0.139 Uiso 1 1 calc R
C9 C 0.0564(9) 0.2381(7) 0.1203(2) 0.0999(12) Uani 1 1 d .
C10 C 0.1535(6) 0.3115(5) 0.19784(15) 0.0762(8) 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'
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 117.23(15) . .
O1 C1 O2 123.44(19) . .
O1 C1 C2 124.94(19) . .
O2 C1 C2 111.62(16) . .
C3 C2 C1 121.34(17) . .
C3 C2 H2 119.3 . .
C1 C2 H2 119.3 . .
C2 C3 C3 123.5(2) . 2_456
C2 C3 H3 118.2 . .
C3 C3 H3 118.2 2_456 .
O2 C4 C5 108.48(18) . .
O2 C4 H4A 110.0 . .
C5 C4 H4A 110.0 . .
O2 C4 H4B 110.0 . .
C5 C4 H4B 110.0 . .
H4A C4 H4B 108.4 . .
C6 C5 C10 117.1(3) . .
C6 C5 C4 122.5(2) . .
C10 C5 C4 120.4(2) . .
F6 C6 C5 120.0(3) . .
F6 C6 C7 118.9(3) . .
C5 C6 C7 121.1(4) . .
F7 C7 C8 120.9(4) . .
F7 C7 C6 118.3(5) . .
C8 C7 C6 120.9(4) . .
C9 C8 C7 118.7(3) . .
C9 C8 H8 120.7 . .
C7 C8 H8 120.7 . .
F9 C9 C8 121.0(4) . .
F9 C9 C10 118.6(4) . .
C8 C9 C10 120.4(4) . .
F10 C10 C9 118.9(3) . .
F10 C10 C5 119.3(2) . .
C9 C10 C5 121.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F6 C6 1.340(4) .
F7 C7 1.349(5) .
F9 C9 1.350(5) .
F10 C10 1.341(4) .
O1 C1 1.205(2) .
O2 C1 1.345(2) .
O2 C4 1.451(3) .
C1 C2 1.472(3) .
C2 C3 1.330(3) .
C2 H2 0.9400 .
C3 C3 1.448(4) 2_456
C3 H3 0.9400 .
C4 C5 1.508(3) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C5 C6 1.380(4) .
C5 C10 1.390(4) .
C6 C7 1.385(5) .
C7 C8 1.382(7) .
C8 C9 1.365(6) .
C8 H8 0.9400 .
C9 C10 1.384(4) .
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 -4.7(3) .
C4 O2 C1 C2 175.43(15) .
O1 C1 C2 C3 -2.1(3) .
O2 C1 C2 C3 177.84(18) .
C1 C2 C3 C3 -179.7(2) 2_456
C1 O2 C4 C5 -103.1(2) .
O2 C4 C5 C6 110.2(2) .
O2 C4 C5 C10 -69.1(3) .
C10 C5 C6 F6 179.8(2) .
C4 C5 C6 F6 0.4(4) .
C10 C5 C6 C7 -0.1(4) .
C4 C5 C6 C7 -179.5(2) .
F6 C6 C7 F7 0.3(4) .
C5 C6 C7 F7 -179.8(2) .
F6 C6 C7 C8 -179.1(3) .
C5 C6 C7 C8 0.8(5) .
F7 C7 C8 C9 179.5(3) .
C6 C7 C8 C9 -1.1(5) .
C7 C8 C9 F9 -179.4(3) .
C7 C8 C9 C10 0.6(5) .
F9 C9 C10 F10 -0.6(4) .
C8 C9 C10 F10 179.3(3) .
F9 C9 C10 C5 -179.8(3) .
C8 C9 C10 C5 0.1(5) .
C6 C5 C10 F10 -179.6(2) .
C4 C5 C10 F10 -0.2(4) .
C6 C5 C10 C9 -0.4(4) .
C4 C5 C10 C9 179.0(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101253897
