#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:21:30 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179574 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/39/4503994.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_4503994
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           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                74.13(2)
_cell_angle_beta                 81.53(2)
_cell_angle_gamma                87.59(3)
_cell_formula_units_Z            1
_cell_length_a                   3.9694(12)
_cell_length_b                   10.829(3)
_cell_length_c                   10.846(3)
_cell_measurement_reflns_used    4160
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     443.5(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    SIR88
_diffrn_ambient_temperature      203(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_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    0.0153
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            1950
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9745
_exptl_absorpt_correction_T_min  0.9500
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             202
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0456
_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)+(0.0717P)²+0.0596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1325
_reflns_number_gt                1428
_reflns_number_total             1950
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060643bsi20060925_055548.cif
_cod_data_source_block           (E,E)-3
_cod_database_code               4503994
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 -0.1288(4) -0.45603(10) 0.84176(13) 0.0782(4) Uani 1 1 d .
F9 F -0.4372(4) -0.17873(12) 1.10281(11) 0.0779(4) Uani 1 1 d .
O1 O 0.3988(3) 0.19965(11) 0.49746(12) 0.0527(4) Uani 1 1 d .
O2 O 0.0455(3) 0.10851(10) 0.67721(11) 0.0415(3) Uani 1 1 d .
C1 C 0.1739(4) 0.20942(14) 0.58125(15) 0.0376(4) Uani 1 1 d .
C2 C 0.0056(4) 0.33018(15) 0.59186(16) 0.0416(4) Uani 1 1 d .
H2 H -0.1553 0.3307 0.6646 0.050 Uiso 1 1 calc R
C3 C 0.0786(4) 0.43878(14) 0.49966(16) 0.0410(4) Uani 1 1 d .
H3 H 0.2442 0.4356 0.4291 0.049 Uiso 1 1 calc R
C4 C 0.2029(4) -0.01257(15) 0.67278(17) 0.0422(4) Uani 1 1 d .
H4A H 0.4442 -0.0105 0.6822 0.051 Uiso 1 1 calc R
H4B H 0.1878 -0.0286 0.5891 0.051 Uiso 1 1 calc R
C5 C 0.0257(4) -0.11784(15) 0.78020(16) 0.0382(4) Uani 1 1 d .
C6 C 0.0285(4) -0.23950(15) 0.76174(17) 0.0431(4) Uani 1 1 d .
H6 H 0.1344 -0.2550 0.6839 0.052 Uiso 1 1 calc R
C7 C -0.1283(5) -0.33698(16) 0.86068(18) 0.0495(5) Uani 1 1 d .
C8 C -0.2858(5) -0.32057(17) 0.97629(18) 0.0520(5) Uani 1 1 d .
H8 H -0.3902 -0.3891 1.0424 0.062 Uiso 1 1 calc R
C9 C -0.2825(5) -0.19885(18) 0.99022(17) 0.0502(5) Uani 1 1 d .
C10 C -0.1321(5) -0.09661(16) 0.89497(17) 0.0469(4) Uani 1 1 d .
H10 H -0.1366 -0.0141 0.9078 0.056 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 114.59(13) . .
O1 C1 O2 122.97(15) . .
O1 C1 C2 125.02(14) . .
O2 C1 C2 112.01(14) . .
C3 C2 C1 120.65(15) . .
C3 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C2 C3 C3 124.6(2) . 2_566
C2 C3 H3 117.7 . .
C3 C3 H3 117.7 2_566 .
O2 C4 C5 109.42(14) . .
O2 C4 H4A 109.8 . .
C5 C4 H4A 109.8 . .
O2 C4 H4B 109.8 . .
C5 C4 H4B 109.8 . .
H4A C4 H4B 108.2 . .
C10 C5 C6 120.28(15) . .
C10 C5 C4 122.06(15) . .
C6 C5 C4 117.65(16) . .
C7 C6 C5 117.99(17) . .
C7 C6 H6 121.0 . .
C5 C6 H6 121.0 . .
F7 C7 C8 118.37(16) . .
F7 C7 C6 117.89(17) . .
C8 C7 C6 123.74(17) . .
C9 C8 C7 116.26(16) . .
C9 C8 H8 121.9 . .
C7 C8 H8 121.9 . .
F9 C9 C8 117.98(16) . .
F9 C9 C10 118.92(17) . .
C8 C9 C10 123.11(17) . .
C9 C10 C5 118.62(16) . .
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 1.360(2) .
F9 C9 1.352(2) .
O1 C1 1.200(2) .
O2 C1 1.3436(18) .
O2 C4 1.438(2) .
C1 C2 1.468(2) .
C2 C3 1.329(2) .
C2 H2 0.9400 .
C3 C3 1.443(3) 2_566
C3 H3 0.9400 .
C4 C5 1.500(2) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C5 C10 1.382(2) .
C5 C6 1.385(2) .
C6 C7 1.376(2) .
C6 H6 0.9400 .
C7 C8 1.370(3) .
C8 C9 1.368(3) .
C8 H8 0.9400 .
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 0.9(2) .
C4 O2 C1 C2 -179.39(14) .
O1 C1 C2 C3 5.4(3) .
O2 C1 C2 C3 -174.34(15) .
C1 C2 C3 C3 178.6(2) 2_566
C1 O2 C4 C5 -177.01(13) .
O2 C4 C5 C10 -28.7(2) .
O2 C4 C5 C6 152.20(15) .
C10 C5 C6 C7 -0.2(2) .
C4 C5 C6 C7 178.88(15) .
C5 C6 C7 F7 179.22(16) .
C5 C6 C7 C8 -0.2(3) .
F7 C7 C8 C9 -179.18(17) .
C6 C7 C8 C9 0.2(3) .
C7 C8 C9 F9 179.65(17) .
C7 C8 C9 C10 0.1(3) .
F9 C9 C10 C5 179.95(16) .
C8 C9 C10 C5 -0.5(3) .
C6 C5 C10 C9 0.6(2) .
C4 C5 C10 C9 -178.50(16) .
