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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/4/50/40/4504001.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_4504001
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           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                106.49(3)
_cell_angle_beta                 98.19(3)
_cell_angle_gamma                98.82(2)
_cell_formula_units_Z            1
_cell_length_a                   3.9341(14)
_cell_length_b                   9.978(4)
_cell_length_c                   12.089(4)
_cell_measurement_reflns_used    3927
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     440.9(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    SIR88
_diffrn_ambient_temperature      203(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_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    0.0227
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            1947
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_correction_T_min  0.9412
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             218
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0420
_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)+(0.0768P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1166
_reflns_number_gt                1346
_reflns_number_total             1947
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060643bsi20060925_060150.cif
_cod_data_source_block           (Z,Z)-4
_cod_database_code               4504001
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
F7 F 1.6170(3) 0.93685(10) 0.31037(10) 0.0521(3) Uani 1 1 d .
F8 F 1.7534(3) 0.89545(10) 0.52309(9) 0.0487(3) Uani 1 1 d .
F9 F 1.4354(3) 0.65553(12) 0.55411(9) 0.0564(4) Uani 1 1 d .
O1 O 0.3652(3) 0.26841(13) -0.00838(11) 0.0474(4) Uani 1 1 d .
O2 O 0.6621(3) 0.36135(11) 0.17621(9) 0.0326(3) Uani 1 1 d .
C1 C 0.4332(4) 0.25831(16) 0.08842(14) 0.0287(4) Uani 1 1 d .
C2 C 0.2892(4) 0.14078(16) 0.12961(14) 0.0342(4) Uani 1 1 d .
H2 H 0.3584 0.1510 0.2098 0.041 Uiso 1 1 calc R
C3 C 0.0668(4) 0.02010(17) 0.06224(14) 0.0333(4) Uani 1 1 d .
H3 H -0.0101 -0.0454 0.1005 0.040 Uiso 1 1 calc R
C4 C 0.8149(4) 0.48192(15) 0.14439(14) 0.0296(4) Uani 1 1 d .
H4A H 0.6289 0.5255 0.1151 0.036 Uiso 1 1 calc R
H4B H 0.9436 0.4502 0.0813 0.036 Uiso 1 1 calc R
C5 C 1.0595(4) 0.59000(16) 0.24865(13) 0.0260(3) Uani 1 1 d .
C6 C 1.2220(4) 0.71533(16) 0.23300(14) 0.0300(4) Uani 1 1 d .
H6 H 1.1738 0.7307 0.1597 0.036 Uiso 1 1 calc R
C7 C 1.4534(4) 0.81642(16) 0.32540(15) 0.0333(4) Uani 1 1 d .
C8 C 1.5248(4) 0.79699(17) 0.43349(14) 0.0325(4) Uani 1 1 d .
C9 C 1.3615(4) 0.67316(18) 0.44755(15) 0.0348(4) Uani 1 1 d .
C10 C 1.1299(4) 0.56831(16) 0.35677(14) 0.0309(4) Uani 1 1 d .
H10 H 1.0221 0.4838 0.3682 0.037 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 114.96(12) . .
O1 C1 O2 121.70(14) . .
O1 C1 C2 127.38(14) . .
O2 C1 C2 110.92(13) . .
C3 C2 C1 125.29(15) . .
C3 C2 H2 117.4 . .
C1 C2 H2 117.4 . .
C2 C3 C3 127.07(19) . 2
C2 C3 H3 116.5 . .
C3 C3 H3 116.5 2 .
O2 C4 C5 110.30(12) . .
O2 C4 H4A 109.6 . .
C5 C4 H4A 109.6 . .
O2 C4 H4B 109.6 . .
C5 C4 H4B 109.6 . .
H4A C4 H4B 108.1 . .
C10 C5 C6 120.01(14) . .
C10 C5 C4 122.62(13) . .
C6 C5 C4 117.36(14) . .
C7 C6 C5 119.49(15) . .
C7 C6 H6 120.3 . .
C5 C6 H6 120.3 . .
F7 C7 C8 118.86(14) . .
F7 C7 C6 119.87(15) . .
C8 C7 C6 121.27(14) . .
F8 C8 C9 120.49(15) . .
F8 C8 C7 121.01(14) . .
C9 C8 C7 118.49(15) . .
F9 C9 C8 117.75(15) . .
F9 C9 C10 120.15(14) . .
C8 C9 C10 122.10(15) . .
C9 C10 C5 118.63(14) . .
C9 C10 H10 120.7 . .
C5 C10 H10 120.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F7 C7 1.3459(18) .
F8 C8 1.3396(18) .
F9 C9 1.3464(19) .
O1 C1 1.199(2) .
O2 C1 1.3484(19) .
O2 C4 1.4366(18) .
C1 C2 1.467(2) .
C2 C3 1.340(2) .
C2 H2 0.9400 .
C3 C3 1.439(3) 2
C3 H3 0.9400 .
C4 C5 1.497(2) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C5 C10 1.381(2) .
C5 C6 1.390(2) .
C6 C7 1.372(2) .
C6 H6 0.9400 .
C7 C8 1.371(2) .
C8 C9 1.369(2) .
C9 C10 1.378(2) .
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 -0.1(2) .
C4 O2 C1 C2 -179.45(13) .
O1 C1 C2 C3 3.7(3) .
O2 C1 C2 C3 -177.02(17) .
C1 C2 C3 C3 1.7(4) 2
C1 O2 C4 C5 179.18(13) .
O2 C4 C5 C10 2.6(2) .
O2 C4 C5 C6 -178.29(13) .
C10 C5 C6 C7 0.4(2) .
C4 C5 C6 C7 -178.80(15) .
C5 C6 C7 F7 178.72(14) .
C5 C6 C7 C8 -0.7(3) .
F7 C7 C8 F8 -0.1(3) .
C6 C7 C8 F8 179.37(16) .
F7 C7 C8 C9 -178.98(15) .
C6 C7 C8 C9 0.5(3) .
F8 C8 C9 F9 0.9(2) .
C7 C8 C9 F9 179.77(16) .
F8 C8 C9 C10 -178.75(16) .
C7 C8 C9 C10 0.1(3) .
F9 C9 C10 C5 179.87(15) .
C8 C9 C10 C5 -0.5(3) .
C6 C5 C10 C9 0.2(2) .
C4 C5 C10 C9 179.36(15) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102332114
