#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:22:48 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179575 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/40/4504004.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_4504004
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
_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                 98.20(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.626(12)
_cell_length_b                   5.409(7)
_cell_length_c                   18.84(2)
_cell_measurement_reflns_used    6274
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.3
_cell_volume                     971(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      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_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  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5054
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.9476
_exptl_absorpt_correction_T_min  0.9148
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.1487
_refine_ls_R_factor_gt           0.1012
_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)+(0.1394P)²+0.9220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3204
_refine_ls_wR_factor_ref         0.3539
_reflns_number_gt                1111
_reflns_number_total             2081
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060643bsi20060925_060238.cif
_cod_data_source_block           (Z,Z)-8
_cod_database_code               4504004
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
_atom_site_disorder_assembly
_atom_site_disorder_group
F6 F 0.2262(4) 0.3929(9) 0.7372(2) 0.1223(16) Uani 1 1 d . . .
F7 F 0.2618(5) 0.3177(12) 0.6021(3) 0.156(2) Uani 1 1 d . . .
F8 F 0.1416(13) -0.076(3) 0.5288(6) 0.089(7) Uiso 0.47(6) 1 d P A 1
F8D1 F 0.157(2) 0.019(8) 0.5279(12) 0.117(10) Uiso 0.27(3) 1 d P A 2
F8D2 F 0.117(2) -0.179(7) 0.5284(9) 0.103(8) Uiso 0.27(3) 1 d P A 2
F9 F -0.0247(5) -0.3887(10) 0.5933(3) 0.149(2) Uani 1 1 d . . .
F10 F -0.0584(4) -0.3193(9) 0.7312(3) 0.1246(16) Uani 1 1 d . A .
O1 O 0.2966(5) 0.2357(9) 0.8948(3) 0.1096(17) Uani 1 1 d . . .
O2 O 0.1567(4) -0.0787(9) 0.8614(2) 0.0966(14) Uani 1 1 d . . .
C1 C 0.2717(6) 0.0218(12) 0.8988(3) 0.0741(14) Uani 1 1 d . . .
C2 C 0.3547(6) -0.1610(11) 0.9423(3) 0.0830(16) Uani 1 1 d . . .
H2 H 0.3266 -0.3250 0.9361 0.100 Uiso 1 1 calc R . .
C3 C 0.4695(6) -0.1153(11) 0.9910(3) 0.0799(15) Uani 1 1 d . . .
H3 H 0.5123 -0.2516 1.0150 0.096 Uiso 1 1 calc R . .
C4 C 0.0645(6) 0.0765(15) 0.8148(3) 0.098(2) Uani 1 1 d . . .
H4A H 0.0834 0.2483 0.8274 0.118 Uiso 1 1 calc R . .
H4B H -0.0320 0.0412 0.8208 0.118 Uiso 1 1 calc R . .
C5 C 0.0834(5) 0.0354(13) 0.7375(3) 0.0856(18) Uani 1 1 d . A .
C6 C 0.1632(6) 0.1888(13) 0.7027(3) 0.0893(18) Uani 1 1 d . . .
C7 C 0.1831(7) 0.1578(17) 0.6340(4) 0.106(2) Uani 1 1 d . A .
C8 C 0.1194(7) -0.0385(19) 0.5960(4) 0.112(3) Uani 1 1 d . . .
C9 C 0.0374(7) -0.2039(16) 0.6295(4) 0.105(2) Uani 1 1 d . A .
C10 C 0.0207(6) -0.1623(13) 0.6992(4) 0.0905(18) 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
F8D2 F8D1 C8 70.0(19) . .
F8D1 F8D2 C8 63.8(18) . .
C1 O2 C4 118.6(5) . .
O1 C1 O2 121.4(5) . .
O1 C1 C2 127.0(5) . .
O2 C1 C2 111.6(5) . .
C3 C2 C1 126.1(6) . .
C3 C2 H2 117.0 . .
C1 C2 H2 117.0 . .
C2 C3 C3 126.9(7) . 3_657
C2 C3 H3 116.5 . .
C3 C3 H3 116.5 3_657 .
O2 C4 C5 110.9(5) . .
O2 C4 H4A 109.5 . .
C5 C4 H4A 109.5 . .
O2 C4 H4B 109.5 . .
C5 C4 H4B 109.5 . .
H4A C4 H4B 108.1 . .
C6 C5 C10 117.0(6) . .
C6 C5 C4 122.0(7) . .
C10 C5 C4 121.0(6) . .
C7 C6 C5 123.8(7) . .
C7 C6 F6 116.1(7) . .
C5 C6 F6 120.1(6) . .
C6 C7 F7 121.0(8) . .
C6 C7 C8 118.9(7) . .
F7 C7 C8 120.0(7) . .
F8 C8 C7 119.6(11) . .
F8 C8 C9 120.6(11) . .
C7 C8 C9 119.7(7) . .
F8 C8 F8D1 22.2(18) . .
C7 C8 F8D1 98.7(18) . .
C9 C8 F8D1 141.4(18) . .
F8 C8 F8D2 24.1(13) . .
C7 C8 F8D2 142.7(16) . .
C9 C8 F8D2 96.9(16) . .
F8D1 C8 F8D2 46(3) . .
F9 C9 C10 121.4(8) . .
F9 C9 C8 119.9(8) . .
C10 C9 C8 118.6(7) . .
F10 C10 C9 118.7(7) . .
F10 C10 C5 119.3(6) . .
C9 C10 C5 121.9(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F6 C6 1.377(8) .
F7 C7 1.346(9) .
F8 C8 1.328(13) .
F8D1 F8D2 1.14(8) .
F8D1 C8 1.42(3) .
F8D2 C8 1.48(3) .
F9 C9 1.305(8) .
F10 C10 1.340(8) .
O1 C1 1.186(7) .
O2 C1 1.340(6) .
O2 C4 1.429(7) .
C1 C2 1.450(8) .
C2 C3 1.355(8) .
C2 H2 0.9300 .
C3 C3 1.400(12) 3_657
C3 H3 0.9300 .
C4 C5 1.508(9) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.361(9) .
C5 C10 1.380(9) .
C6 C7 1.344(10) .
C7 C8 1.375(12) .
C8 C9 1.402(11) .
C9 C10 1.364(10) .
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 1.2(8) .
C4 O2 C1 C2 -179.0(5) .
O1 C1 C2 C3 6.3(11) .
O2 C1 C2 C3 -173.5(6) .
C1 C2 C3 C3 0.0(12) 3_657
C1 O2 C4 C5 103.5(7) .
O2 C4 C5 C6 -98.9(7) .
O2 C4 C5 C10 80.6(6) .
C10 C5 C6 C7 0.2(9) .
C4 C5 C6 C7 179.7(6) .
C10 C5 C6 F6 178.5(5) .
C4 C5 C6 F6 -1.9(8) .
C5 C6 C7 F7 179.1(6) .
F6 C6 C7 F7 0.7(9) .
C5 C6 C7 C8 0.4(10) .
F6 C6 C7 C8 -178.1(5) .
C6 C7 C8 F8 -177.9(8) .
F7 C7 C8 F8 3.3(11) .
C6 C7 C8 C9 -1.1(10) .
F7 C7 C8 C9 -179.9(6) .
C6 C7 C8 F8D1 174.2(11) .
F7 C7 C8 F8D1 -4.6(12) .
C6 C7 C8 F8D2 -168.5(15) .
F7 C7 C8 F8D2 12.7(19) .
F8D2 F8D1 C8 F8 4(3) .
F8D2 F8D1 C8 C7 165.6(11) .
F8D2 F8D1 C8 C9 -21(2) .
F8D1 F8D2 C8 F8 -4(3) .
F8D1 F8D2 C8 C7 -24(2) .
F8D1 F8D2 C8 C9 167.0(13) .
F8 C8 C9 F9 -4.0(11) .
C7 C8 C9 F9 179.2(6) .
F8D1 C8 C9 F9 7(2) .
F8D2 C8 C9 F9 -8.5(10) .
F8 C8 C9 C10 178.1(8) .
C7 C8 C9 C10 1.3(10) .
F8D1 C8 C9 C10 -171.3(18) .
F8D2 C8 C9 C10 173.7(9) .
F9 C9 C10 F10 1.7(9) .
C8 C9 C10 F10 179.5(5) .
F9 C9 C10 C5 -178.6(5) .
C8 C9 C10 C5 -0.8(9) .
C6 C5 C10 F10 179.7(5) .
C4 C5 C10 F10 0.2(8) .
C6 C5 C10 C9 0.1(8) .
C4 C5 C10 C9 -179.5(6) .
