#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/64/1506465.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_1506465
loop_
_publ_author_name
'Liu, Jin'
'Wendt, Natalie L.'
'Boarman, Kelly J.'
_publ_section_title
;
 Trifluoromethyl groups in crystal design of 1,4-diphenyl-1,3-butadienes
 for topochemical [2 + 2] photodimerization.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1007
_journal_page_last               1010
_journal_paper_doi               10.1021/ol0475111
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C18 H10 F8'
_chemical_formula_sum            'C18 H10 F8'
_chemical_formula_weight         378.26
_chemical_name_common            04256a
_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                104.706(2)
_cell_angle_beta                 97.670(2)
_cell_angle_gamma                104.072(2)
_cell_formula_units_Z            1
_cell_length_a                   4.7834(9)
_cell_length_b                   7.7026(15)
_cell_length_c                   11.290(2)
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.86
_cell_volume                     381.74(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4509
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.9649
_exptl_absorpt_correction_T_min  0.9449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             190
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1731
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0351
_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)+(0.0412P)²+0.1826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0966
_reflns_number_gt                1448
_reflns_number_total             1731
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0475111si20050128_024635.cif
_cod_data_source_block           04256a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        381.72(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1506465
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
C1 C -0.0833(3) 0.29841(19) 0.29319(13) 0.0199(3) Uani 1 1 d .
C2 C -0.3070(3) 0.12635(19) 0.24358(13) 0.0188(3) Uani 1 1 d .
C3 C -0.5424(3) 0.1011(2) 0.14753(13) 0.0211(3) Uani 1 1 d .
H3A H -0.6925 -0.0152 0.1149 0.025 Uiso 1 1 calc R
C4 C -0.5521(3) 0.2483(2) 0.10126(13) 0.0227(3) Uani 1 1 d .
F1 F -0.7816(2) 0.22380(13) 0.00719(8) 0.0306(2) Uani 1 1 d .
C5 C -0.3393(3) 0.4190(2) 0.14535(14) 0.0248(3) Uani 1 1 d .
H5A H -0.3513 0.5182 0.1110 0.030 Uiso 1 1 calc R
C6 C -0.1079(3) 0.4422(2) 0.24097(14) 0.0242(3) Uani 1 1 d .
H6A H 0.0396 0.5597 0.2724 0.029 Uiso 1 1 calc R
C7 C -0.3024(3) -0.0356(2) 0.29450(14) 0.0222(3) Uani 1 1 d .
F2 F -0.3129(2) 0.00493(14) 0.41645(9) 0.0335(2) Uani 1 1 d .
F3 F -0.05760(18) -0.09111(12) 0.28438(9) 0.0267(2) Uani 1 1 d .
F4 F -0.52999(19) -0.18796(12) 0.23498(9) 0.0321(2) Uani 1 1 d .
C8 C 0.1682(3) 0.3280(2) 0.39463(14) 0.0238(3) Uani 1 1 d .
H8A H 0.1811 0.2232 0.4225 0.029 Uiso 1 1 calc R
C9 C 0.3791(3) 0.4892(2) 0.45062(13) 0.0226(3) Uani 1 1 d .
H9A H 0.3692 0.5954 0.4239 0.027 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0190(6) 0.0206(7) 0.0196(7) 0.0048(5) 0.0051(5) 0.0057(5)
C2 0.0184(6) 0.0200(7) 0.0205(7) 0.0063(5) 0.0079(5) 0.0077(5)
C3 0.0170(6) 0.0211(7) 0.0232(7) 0.0041(5) 0.0047(5) 0.0043(5)
C4 0.0200(7) 0.0278(7) 0.0199(7) 0.0059(6) 0.0015(5) 0.0087(6)
F1 0.0257(5) 0.0331(5) 0.0290(5) 0.0097(4) -0.0059(4) 0.0069(4)
C5 0.0273(7) 0.0237(7) 0.0253(7) 0.0104(6) 0.0035(6) 0.0087(6)
C6 0.0235(7) 0.0202(7) 0.0263(7) 0.0068(6) 0.0025(6) 0.0033(6)
C7 0.0193(6) 0.0216(7) 0.0273(7) 0.0087(6) 0.0073(5) 0.0058(5)
F2 0.0444(6) 0.0364(5) 0.0307(5) 0.0196(4) 0.0178(4) 0.0162(4)
F3 0.0209(4) 0.0255(5) 0.0391(5) 0.0144(4) 0.0075(4) 0.0105(3)
F4 0.0217(4) 0.0221(5) 0.0512(6) 0.0154(4) 0.0037(4) 0.0017(4)
C8 0.0238(7) 0.0240(7) 0.0245(7) 0.0094(6) 0.0030(6) 0.0075(6)
C9 0.0220(7) 0.0246(7) 0.0220(7) 0.0069(6) 0.0033(6) 0.0086(6)
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'
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
C6 C1 C2 116.93(13) . .
C6 C1 C8 120.74(13) . .
C2 C1 C8 122.34(13) . .
C3 C2 C1 121.44(13) . .
C3 C2 C7 117.62(12) . .
C1 C2 C7 120.93(12) . .
C4 C3 C2 118.36(13) . .
C4 C3 H3A 120.8 . .
C2 C3 H3A 120.8 . .
F1 C4 C3 118.46(13) . .
F1 C4 C5 118.71(13) . .
C3 C4 C5 122.83(13) . .
C4 C5 C6 118.15(13) . .
C4 C5 H5A 120.9 . .
C6 C5 H5A 120.9 . .
C5 C6 C1 122.29(13) . .
C5 C6 H6A 118.9 . .
C1 C6 H6A 118.9 . .
F4 C7 F2 106.45(11) . .
F4 C7 F3 105.82(11) . .
F2 C7 F3 106.04(11) . .
F4 C7 C2 112.59(12) . .
F2 C7 C2 112.56(12) . .
F3 C7 C2 112.83(11) . .
C9 C8 C1 125.68(13) . .
C9 C8 H8A 117.2 . .
C1 C8 H8A 117.2 . .
C8 C9 C9 123.55(17) . 2_666
C8 C9 H9A 118.2 . .
C9 C9 H9A 118.2 2_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.402(2) .
C1 C2 1.4103(19) .
C1 C8 1.4754(19) .
C2 C3 1.3937(19) .
C2 C7 1.5035(19) .
C3 C4 1.371(2) .
C3 H3A 0.9500 .
C4 F1 1.3619(16) .
C4 C5 1.377(2) .
C5 C6 1.382(2) .
C5 H5A 0.9500 .
C6 H6A 0.9500 .
C7 F4 1.3406(17) .
C7 F2 1.3428(18) .
C7 F3 1.3499(16) .
C8 C9 1.334(2) .
C8 H8A 0.9500 .
C9 C9 1.441(3) 2_666
C9 H9A 0.9500 .
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
C6 C1 C2 C3 -0.3(2) .
C8 C1 C2 C3 -179.85(13) .
C6 C1 C2 C7 -179.16(13) .
C8 C1 C2 C7 1.3(2) .
C1 C2 C3 C4 0.2(2) .
C7 C2 C3 C4 179.09(12) .
C2 C3 C4 F1 179.84(12) .
C2 C3 C4 C5 0.2(2) .
F1 C4 C5 C6 179.88(13) .
C3 C4 C5 C6 -0.5(2) .
C4 C5 C6 C1 0.3(2) .
C2 C1 C6 C5 0.1(2) .
C8 C1 C6 C5 179.57(13) .
C3 C2 C7 F4 1.94(18) .
C1 C2 C7 F4 -179.19(12) .
C3 C2 C7 F2 -118.38(14) .
C1 C2 C7 F2 60.48(17) .
C3 C2 C7 F3 121.65(13) .
C1 C2 C7 F3 -59.49(17) .
C6 C1 C8 C9 4.3(2) .
C2 C1 C8 C9 -176.23(14) .
C1 C8 C9 C9 -179.90(16) 2_666
