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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/4/50/39/4503995.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_4503995
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 H12 F6 O4 '
_chemical_formula_sum            'C20 H12 F6 O4'
_chemical_formula_weight         430.30
_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                 96.466(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.8986(7)
_cell_length_b                   20.073(5)
_cell_length_c                   11.586(2)
_cell_measurement_reflns_used    5222
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.7
_cell_volume                     900.9(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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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    0.0275
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2022
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9424
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0666
_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)+(0.0692P)²+1.4349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1825
_refine_ls_wR_factor_ref         0.1906
_reflns_number_gt                1391
_reflns_number_total             2022
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060643bsi20060925_055608.cif
_cod_data_source_block           (E,E)-4
_cod_database_code               4503995
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
F7 F 1.3011(7) 0.19240(13) 1.27981(19) 0.0607(7) Uani 1 1 d .
F8 F 1.2100(7) 0.31349(11) 1.1804(2) 0.0579(7) Uani 1 1 d .
F9 F 0.8623(8) 0.32536(11) 0.9678(2) 0.0636(8) Uani 1 1 d .
O1 O 0.4072(7) -0.00745(13) 0.8044(2) 0.0465(7) Uani 1 1 d .
O2 O 0.7077(6) 0.08783(11) 0.82546(17) 0.0304(5) Uani 1 1 d .
C1 C 0.5576(8) 0.03706(15) 0.7627(3) 0.0295(7) Uani 1 1 d .
C2 C 0.6047(9) 0.04335(16) 0.6389(3) 0.0337(7) Uani 1 1 d .
H2 H 0.7245 0.0804 0.6140 0.040 Uiso 1 1 calc R
C3 C 0.4822(9) -0.00196(17) 0.5614(3) 0.0337(7) Uani 1 1 d .
H3 H 0.3652 -0.0389 0.5880 0.040 Uiso 1 1 calc R
C4 C 0.6635(9) 0.08493(16) 0.9477(3) 0.0317(7) Uani 1 1 d .
H4A H 0.7787 0.0453 0.9829 0.038 Uiso 1 1 calc R
H4B H 0.4175 0.0821 0.9574 0.038 Uiso 1 1 calc R
C5 C 0.8176(7) 0.14678(16) 1.0065(3) 0.0265(6) Uani 1 1 d .
C6 C 0.9924(9) 0.14072(17) 1.1170(3) 0.0336(7) Uani 1 1 d .
H6 H 1.0204 0.0988 1.1529 0.040 Uiso 1 1 calc R
C7 C 1.1242(9) 0.19696(18) 1.1736(3) 0.0355(8) Uani 1 1 d .
C8 C 1.0810(9) 0.25880(17) 1.1243(3) 0.0368(8) Uani 1 1 d .
C9 C 0.9041(10) 0.26409(17) 1.0146(3) 0.0384(8) Uani 1 1 d .
C10 C 0.7738(9) 0.20878(17) 0.9549(3) 0.0347(8) Uani 1 1 d .
H10 H 0.6561 0.2130 0.8799 0.042 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 113.9(2) . .
O1 C1 O2 123.3(3) . .
O1 C1 C2 125.2(3) . .
O2 C1 C2 111.5(3) . .
C3 C2 C1 121.6(3) . .
C3 C2 H2 119.2 . .
C1 C2 H2 119.2 . .
C2 C3 C3 124.0(4) . 3_656
C2 C3 H3 118.0 . .
C3 C3 H3 118.0 3_656 .
O2 C4 C5 108.9(2) . .
O2 C4 H4A 109.9 . .
C5 C4 H4A 109.9 . .
O2 C4 H4B 109.9 . .
C5 C4 H4B 109.9 . .
H4A C4 H4B 108.3 . .
C10 C5 C6 120.1(3) . .
C10 C5 C4 121.5(3) . .
C6 C5 C4 118.3(3) . .
C7 C6 C5 119.1(3) . .
C7 C6 H6 120.5 . .
C5 C6 H6 120.5 . .
F7 C7 C8 118.0(3) . .
F7 C7 C6 120.4(3) . .
C8 C7 C6 121.6(3) . .
F8 C8 C7 121.1(3) . .
F8 C8 C9 120.2(3) . .
C7 C8 C9 118.6(3) . .
F9 C9 C10 120.9(3) . .
F9 C9 C8 117.8(3) . .
C10 C9 C8 121.3(3) . .
C9 C10 C5 119.3(3) . .
C9 C10 H10 120.4 . .
C5 C10 H10 120.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F7 C7 1.345(4) .
F8 C8 1.344(4) .
F9 C9 1.347(4) .
O1 C1 1.200(4) .
O2 C1 1.347(4) .
O2 C4 1.447(3) .
C1 C2 1.472(4) .
C2 C3 1.328(4) .
C2 H2 0.9400 .
C3 C3 1.448(6) 3_656
C3 H3 0.9400 .
C4 C5 1.508(4) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C5 C10 1.383(5) .
C5 C6 1.387(4) .
C6 C7 1.375(5) .
C6 H6 0.9400 .
C7 C8 1.369(5) .
C8 C9 1.380(5) .
C9 C10 1.375(5) .
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 -1.6(5) .
C4 O2 C1 C2 178.8(3) .
O1 C1 C2 C3 -0.7(6) .
O2 C1 C2 C3 178.9(3) .
C1 C2 C3 C3 179.4(4) 3_656
C1 O2 C4 C5 -175.6(3) .
O2 C4 C5 C10 41.3(4) .
O2 C4 C5 C6 -141.7(3) .
C10 C5 C6 C7 -0.8(5) .
C4 C5 C6 C7 -177.8(3) .
C5 C6 C7 F7 -178.6(3) .
C5 C6 C7 C8 1.3(5) .
F7 C7 C8 F8 -0.3(5) .
C6 C7 C8 F8 179.8(3) .
F7 C7 C8 C9 179.1(3) .
C6 C7 C8 C9 -0.8(5) .
F8 C8 C9 F9 -1.0(5) .
C7 C8 C9 F9 179.6(3) .
F8 C8 C9 C10 179.2(3) .
C7 C8 C9 C10 -0.2(5) .
F9 C9 C10 C5 -179.1(3) .
C8 C9 C10 C5 0.8(5) .
C6 C5 C10 C9 -0.2(5) .
C4 C5 C10 C9 176.7(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102332118
