#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/00/01/8000163.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_8000163
loop_
_publ_author_name
'Mori, Yutaka'
'Matsumoto, Akikazu'
_publ_section_title
;
 Photodimerization Mechanism of Bis(3,4,5-trifluorobenzyl) (E,E)-Muconate
 in a Columnar Assembly in the Crystalline State
;
_journal_issue                   4
_journal_name_full               'Chemistry Letters'
_journal_page_first              510
_journal_paper_doi               10.1246/cl.2007.510
_journal_volume                  36
_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                 96.784(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.966(2)
_cell_length_b                   20.041(10)
_cell_length_c                   11.556(6)
_cell_measurement_reflns_used    6747
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.0
_cell_volume                     912.1(8)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8431
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_correction_T_min  0.9362
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0697
_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)+(0.0902P)²+0.6550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1943
_refine_ls_wR_factor_ref         0.2075
_reflns_number_gt                1333
_reflns_number_total             2079
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            36-510sup1.cif
_cod_data_source_block           0
_cod_original_cell_volume        912.0(8)
_cod_database_code               8000163
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 0.8010(7) 0.69125(14) 0.77765(19) 0.0954(9) Uani 1 1 d .
F8 F 0.7110(7) 0.81249(12) 0.6797(2) 0.0904(9) Uani 1 1 d .
F9 F 0.3652(8) 0.82486(11) 0.4684(2) 0.1014(10) Uani 1 1 d .
O1 O -0.0939(8) 0.49317(12) 0.3035(2) 0.0703(8) Uani 1 1 d .
O2 O 0.2032(5) 0.58771(10) 0.32513(16) 0.0456(6) Uani 1 1 d .
C1 C 0.0558(8) 0.53710(14) 0.2624(2) 0.0447(7) Uani 1 1 d .
C2 C 0.1026(9) 0.54296(16) 0.1389(3) 0.0502(8) Uani 1 1 d .
H2 H 0.2217 0.5794 0.1146 0.060 Uiso 1 1 calc R
C3 C -0.0183(9) 0.49841(16) 0.0613(2) 0.0497(8) Uani 1 1 d .
H3 H -0.1358 0.4623 0.0873 0.060 Uiso 1 1 calc R
C4 C 0.1587(9) 0.58559(16) 0.4467(2) 0.0491(8) Uani 1 1 d .
H4A H 0.2663 0.5459 0.4823 0.059 Uiso 1 1 calc R
H4B H -0.0813 0.5838 0.4556 0.059 Uiso 1 1 calc R
C5 C 0.3152(7) 0.64683(15) 0.5057(2) 0.0404(7) Uani 1 1 d .
C6 C 0.4900(8) 0.64060(17) 0.6152(3) 0.0498(8) Uani 1 1 d .
H6 H 0.5180 0.5989 0.6503 0.060 Uiso 1 1 calc R
C7 C 0.6226(9) 0.69642(19) 0.6722(3) 0.0565(9) Uani 1 1 d .
C8 C 0.5818(9) 0.75790(17) 0.6232(3) 0.0561(9) Uani 1 1 d .
C9 C 0.4065(10) 0.76365(16) 0.5145(3) 0.0590(9) Uani 1 1 d .
C10 C 0.2739(9) 0.70885(17) 0.4547(3) 0.0533(8) Uani 1 1 d .
H10 H 0.1573 0.7134 0.3804 0.064 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 114.2(2) . .
O1 C1 O2 123.3(3) . .
O1 C1 C2 125.0(3) . .
O2 C1 C2 111.6(3) . .
C3 C2 C1 122.1(3) . .
C3 C2 H2 118.9 . .
C1 C2 H2 118.9 . .
C2 C3 C3 124.7(4) . 3_565
C2 C3 H3 117.7 . .
C3 C3 H3 117.7 3_565 .
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 119.9(3) . .
C6 C5 C4 118.7(3) . .
C10 C5 C4 121.4(3) . .
C7 C6 C5 119.4(3) . .
C7 C6 H6 120.3 . .
C5 C6 H6 120.3 . .
F7 C7 C8 118.3(3) . .
F7 C7 C6 120.4(3) . .
C8 C7 C6 121.3(3) . .
F8 C8 C7 121.1(3) . .
F8 C8 C9 120.1(3) . .
C7 C8 C9 118.9(3) . .
F9 C9 C8 117.9(3) . .
F9 C9 C10 120.8(3) . .
C8 C9 C10 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 1.339(4) .
F8 C8 1.344(4) .
F9 C9 1.339(4) .
O1 C1 1.192(4) .
O2 C1 1.340(3) .
O2 C4 1.437(3) .
C1 C2 1.465(4) .
C2 C3 1.315(4) .
C2 H2 0.9300 .
C3 C3 1.442(6) 3_565
C3 H3 0.9300 .
C4 C5 1.502(4) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.375(4) .
C5 C10 1.377(5) .
C6 C7 1.371(5) .
C6 H6 0.9300 .
C7 C8 1.358(5) .
C8 C9 1.367(5) .
C9 C10 1.369(5) .
C10 H10 0.9300 .
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 -1.4(5) .
C4 O2 C1 C2 178.6(3) .
O1 C1 C2 C3 -0.6(6) .
O2 C1 C2 C3 179.4(3) .
C1 C2 C3 C3 179.7(4) 3_565
C1 O2 C4 C5 -176.4(3) .
O2 C4 C5 C6 -140.4(3) .
O2 C4 C5 C10 42.5(4) .
C10 C5 C6 C7 -0.3(5) .
C4 C5 C6 C7 -177.4(3) .
C5 C6 C7 F7 -178.3(3) .
C5 C6 C7 C8 0.7(5) .
F7 C7 C8 F8 -1.3(5) .
C6 C7 C8 F8 179.7(3) .
F7 C7 C8 C9 178.6(3) .
C6 C7 C8 C9 -0.4(6) .
F8 C8 C9 F9 -1.0(5) .
C7 C8 C9 F9 179.1(3) .
F8 C8 C9 C10 179.6(3) .
C7 C8 C9 C10 -0.3(6) .
F9 C9 C10 C5 -178.6(3) .
C8 C9 C10 C5 0.7(5) .
C6 C5 C10 C9 -0.4(5) .
C4 C5 C10 C9 176.6(3) .
