#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/39/4503997.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_4503997
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 H8 F10 O4 '
_chemical_formula_sum            'C20 H8 F10 O4'
_chemical_formula_weight         502.26
_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                93.41(4)
_cell_angle_beta                 95.44(3)
_cell_angle_gamma                105.30(4)
_cell_formula_units_Z            1
_cell_length_a                   5.200(2)
_cell_length_b                   5.486(2)
_cell_length_c                   17.773(7)
_cell_measurement_reflns_used    4437
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.5
_cell_volume                     485.0(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 0.904
_diffrn_measured_fraction_theta_max 0.904
_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    0.0114
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            1994
_diffrn_reflns_theta_full        27.39
_diffrn_reflns_theta_max         27.39
_diffrn_reflns_theta_min         3.87
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.9560
_exptl_absorpt_correction_T_min  0.9228
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             250
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0594
_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)+(0.0945P)²+0.1630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1647
_refine_ls_wR_factor_ref         0.1806
_reflns_number_gt                1450
_reflns_number_total             1994
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060643bsi20060925_055706.cif
_cod_data_source_block           (E,E)-8
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_diffrn_measurement_device_typ' was replaced with
'_diffrn_measurement_device_type' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_database_code               4503997
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 0.3159(4) 0.8062(4) 0.25051(14) 0.0942(7) Uani 1 1 d .
F7 F 0.1197(5) 0.6787(7) 0.10472(17) 0.1572(14) Uani 1 1 d .
F8 F 0.2789(7) 0.3161(7) 0.02251(13) 0.1787(18) Uani 1 1 d .
F9 F 0.6443(7) 0.0980(6) 0.08779(15) 0.1552(14) Uani 1 1 d .
F10 F 0.8373(4) 0.2265(4) 0.23389(13) 0.0935(7) Uani 1 1 d .
O1 O 0.2744(4) 0.5578(3) 0.40796(10) 0.0568(5) Uani 1 1 d .
O2 O 0.5818(3) 0.3702(3) 0.37089(9) 0.0516(4) Uani 1 1 d .
C1 C 0.3670(4) 0.3779(4) 0.40574(11) 0.0407(5) Uani 1 1 d .
C2 C 0.2621(4) 0.1421(4) 0.44141(12) 0.0434(5) Uani 1 1 d .
H2 H 0.3426 0.0087 0.4354 0.052 Uiso 1 1 calc R
C3 C 0.0556(4) 0.1138(4) 0.48206(12) 0.0427(5) Uani 1 1 d .
H3 H -0.0221 0.2493 0.4877 0.051 Uiso 1 1 calc R
C4 C 0.6925(5) 0.5846(5) 0.32852(14) 0.0523(6) Uani 1 1 d .
H4A H 0.8887 0.6221 0.3336 0.063 Uiso 1 1 calc R
H4B H 0.6446 0.7349 0.3486 0.063 Uiso 1 1 calc R
C5 C 0.5823(5) 0.5211(5) 0.24679(15) 0.0581(6) Uani 1 1 d .
C6 C 0.4002(6) 0.6281(7) 0.21144(19) 0.0755(9) Uani 1 1 d .
C7 C 0.2967(7) 0.5657(10) 0.1360(3) 0.1029(14) Uani 1 1 d .
C8 C 0.3786(11) 0.3822(12) 0.0953(2) 0.122(2) Uani 1 1 d .
C9 C 0.5614(10) 0.2738(8) 0.1280(2) 0.1043(15) Uani 1 1 d .
C10 C 0.6592(7) 0.3395(6) 0.20294(18) 0.0755(9) 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 116.75(17) . .
O1 C1 O2 123.76(19) . .
O1 C1 C2 124.9(2) . .
O2 C1 C2 111.38(17) . .
C3 C2 C1 121.38(19) . .
C3 C2 H2 119.3 . .
C1 C2 H2 119.3 . .
C2 C3 C3 123.6(2) . 2_556
C2 C3 H3 118.2 . .
C3 C3 H3 118.2 2_556 .
O2 C4 C5 109.1(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 . .
C6 C5 C10 116.3(3) . .
C6 C5 C4 123.5(3) . .
C10 C5 C4 120.2(3) . .
F6 C6 C5 119.6(3) . .
F6 C6 C7 117.3(4) . .
C5 C6 C7 123.1(4) . .
F7 C7 C8 121.8(5) . .
F7 C7 C6 120.0(5) . .
C8 C7 C6 118.1(4) . .
F8 C8 C9 120.1(7) . .
F8 C8 C7 119.3(6) . .
C9 C8 C7 120.6(4) . .
F9 C9 C8 120.5(5) . .
F9 C9 C10 119.8(5) . .
C8 C9 C10 119.7(4) . .
F10 C10 C9 118.2(4) . .
F10 C10 C5 119.6(3) . .
C9 C10 C5 122.2(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F6 C6 1.353(4) .
F7 C7 1.336(5) .
F8 C8 1.338(5) .
F9 C9 1.349(5) .
F10 C10 1.339(4) .
O1 C1 1.207(2) .
O2 C1 1.336(3) .
O2 C4 1.453(3) .
C1 C2 1.471(3) .
C2 C3 1.331(3) .
C2 H2 0.9400 .
C3 C3 1.443(4) 2_556
C3 H3 0.9400 .
C4 C5 1.495(4) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C5 C6 1.364(4) .
C5 C10 1.392(4) .
C6 C7 1.384(5) .
C7 C8 1.384(8) .
C8 C9 1.353(8) .
C9 C10 1.371(5) .
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 -5.2(3) .
C4 O2 C1 C2 175.55(18) .
O1 C1 C2 C3 -2.2(3) .
O2 C1 C2 C3 177.01(19) .
C1 C2 C3 C3 179.7(2) 2_556
C1 O2 C4 C5 -96.2(2) .
O2 C4 C5 C6 108.8(3) .
O2 C4 C5 C10 -69.5(3) .
C10 C5 C6 F6 180.0(2) .
C4 C5 C6 F6 1.6(4) .
C10 C5 C6 C7 -0.8(4) .
C4 C5 C6 C7 -179.1(3) .
F6 C6 C7 F7 -0.4(4) .
C5 C6 C7 F7 -179.7(3) .
F6 C6 C7 C8 -179.4(3) .
C5 C6 C7 C8 1.3(5) .
F7 C7 C8 F8 0.2(6) .
C6 C7 C8 F8 179.1(3) .
F7 C7 C8 C9 178.9(3) .
C6 C7 C8 C9 -2.1(6) .
F8 C8 C9 F9 -0.1(6) .
C7 C8 C9 F9 -178.9(3) .
F8 C8 C9 C10 -178.9(3) .
C7 C8 C9 C10 2.4(6) .
F9 C9 C10 F10 0.4(5) .
C8 C9 C10 F10 179.2(3) .
F9 C9 C10 C5 179.4(3) .
C8 C9 C10 C5 -1.8(5) .
C6 C5 C10 F10 180.0(2) .
C4 C5 C10 F10 -1.6(4) .
C6 C5 C10 C9 1.0(4) .
C4 C5 C10 C9 179.4(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102245549
