#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:21:30 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179574 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/39/4503993.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_4503993
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 H14 F4 O4 '
_chemical_formula_sum            'C20 H14 F4 O4'
_chemical_formula_weight         394.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 98.82
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   19.165(3)
_cell_length_b                   8.2749(13)
_cell_length_c                   5.4329(8)
_cell_measurement_reflns_used    4526
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      3.8
_cell_volume                     851.4(2)
_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 0.998
_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  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7868
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_correction_T_min  0.9417
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1940
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0370
_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)+(0.0493P)²+0.0119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0916
_reflns_number_gt                1394
_reflns_number_total             1940
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060643bsi20060925_055533.cif
_cod_data_source_block           (E,E)-2
_cod_database_code               4503993
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, 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 0.76868(4) 0.04771(11) 0.50636(14) 0.0479(3) Uani 1 1 d .
F10 F 0.82662(5) 0.34094(10) -0.17107(16) 0.0511(3) Uani 1 1 d .
O1 O 0.58192(5) 0.20613(13) 0.05362(18) 0.0435(3) Uani 1 1 d .
O2 O 0.68386(5) 0.17999(11) -0.09943(16) 0.0337(2) Uani 1 1 d .
C1 C 0.61403(7) 0.16149(15) -0.1085(2) 0.0301(3) Uani 1 1 d .
C2 C 0.58352(7) 0.08216(16) -0.3423(2) 0.0343(3) Uani 1 1 d .
H2 H 0.6125 0.0618 -0.4636 0.041 Uiso 1 1 calc R
C3 C 0.51623(7) 0.03846(16) -0.3868(2) 0.0335(3) Uani 1 1 d .
H3 H 0.4880 0.0589 -0.2631 0.040 Uiso 1 1 calc R
C4 C 0.72109(7) 0.26298(17) 0.1173(2) 0.0324(3) Uani 1 1 d .
H4A H 0.6972 0.2447 0.2620 0.039 Uiso 1 1 calc R
H4B H 0.7223 0.3795 0.0859 0.039 Uiso 1 1 calc R
C5 C 0.79416(7) 0.19653(15) 0.1648(2) 0.0277(3) Uani 1 1 d .
C6 C 0.81590(7) 0.08948(16) 0.3566(2) 0.0330(3) Uani 1 1 d .
C7 C 0.88223(8) 0.02347(18) 0.4033(3) 0.0431(4) Uani 1 1 d .
H7 H 0.8948 -0.0488 0.5362 0.052 Uiso 1 1 calc R
C8 C 0.92996(8) 0.06665(19) 0.2488(3) 0.0469(4) Uani 1 1 d .
H8 H 0.9757 0.0223 0.2766 0.056 Uiso 1 1 calc R
C9 C 0.91208(7) 0.17309(19) 0.0552(3) 0.0441(4) Uani 1 1 d .
H9 H 0.9449 0.2024 -0.0490 0.053 Uiso 1 1 calc R
C10 C 0.84499(7) 0.23513(16) 0.0188(2) 0.0338(3) 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 116.6(7) . .
O1 C1 O2 123.8(6) . .
O1 C1 C2 126.0(2) . .
O2 C1 C2 110.2(8) . .
C3 C2 C1 121.8(8) . .
C3 C2 H2 119.1 . .
C1 C2 H2 119.1 . .
C2 C3 C3 123.9(7) . 3_654
C2 C3 H3 118.1 . .
C3 C3 H3 118.1 3_654 .
O2 C4 C5 107.3(7) . .
O2 C4 H4A 110.2 . .
C5 C4 H4A 110.2 . .
O2 C4 H4B 110.2 . .
C5 C4 H4B 110.2 . .
H4A C4 H4B 108.5 . .
C6 C5 C10 115.0(3) . .
C6 C5 C4 122.3(7) . .
C10 C5 C4 122.7(4) . .
F6 C6 C7 118.3(4) . .
F6 C6 C5 117.7(3) . .
C7 C6 C5 124.0(6) . .
C6 C7 C8 117.8(4) . .
C6 C7 H7 121.1 . .
C8 C7 H7 121.1 . .
C9 C8 C7 121.4(3) . .
C9 C8 H8 119.3 . .
C7 C8 H8 119.3 . .
C10 C9 C8 118.0(7) . .
C10 C9 H9 121.0 . .
C8 C9 H9 121.0 . .
F10 C10 C9 118.6(7) . .
F10 C10 C5 117.4(3) . .
C9 C10 C5 123.9(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F6 C6 1.352(10) .
F10 C10 1.358(5) .
O1 C1 1.207(8) .
O2 C1 1.3405(17) .
O2 C4 1.452(10) .
C1 C2 1.469(9) .
C2 C3 1.325(4) .
C2 H2 0.9400 .
C3 C3 1.439(10) 3_654
C3 H3 0.9400 .
C4 C5 1.490(5) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C5 C6 1.382(6) .
C5 C10 1.384(10) .
C6 C7 1.371(5) .
C7 C8 1.380(10) .
C7 H7 0.9400 .
C8 C9 1.374(5) .
C8 H8 0.9400 .
C9 C10 1.370(4) .
C9 H9 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 -1.75(19) .
C4 O2 C1 C2 177.58(10) .
O1 C1 C2 C3 -6.3(2) .
O2 C1 C2 C3 174.43(13) .
C1 C2 C3 C3 179.56(15) 3_654
C1 O2 C4 C5 149.78(13) .
O2 C4 C5 C6 -104.56(13) .
O2 C4 C5 C10 74.46(15) .
C10 C5 C6 F6 179.70(11) .
C4 C5 C6 F6 -1.21(18) .
C10 C5 C6 C7 -0.35(19) .
C4 C5 C6 C7 178.74(13) .
F6 C6 C7 C8 179.84(12) .
C5 C6 C7 C8 -0.1(2) .
C6 C7 C8 C9 0.4(2) .
C7 C8 C9 C10 -0.3(2) .
C8 C9 C10 F10 179.74(12) .
C8 C9 C10 C5 -0.2(2) .
C6 C5 C10 F10 -179.46(11) .
C4 C5 C10 F10 1.46(18) .
C6 C5 C10 C9 0.53(19) .
C4 C5 C10 C9 -178.56(13) .
