#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:28:12 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180140 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/37/7103797.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_7103797
loop_
_publ_author_name
'Jin Liu'
'Elisia M. Murray'
'Young Junior,Victor G. '
_publ_section_title
;
ð Stacking interactions in some crystalline cisoid 
E,E-1,4-diaryl-1,3-butadienes
;
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/b301578e
_journal_year                    2003
_chemical_formula_sum            'C21 H10 F10'
_chemical_formula_weight         452.29
_chemical_name_common            02258a
_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                69.683(2)
_cell_angle_beta                 78.016(2)
_cell_angle_gamma                84.341(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1151(11)
_cell_length_b                   9.1761(11)
_cell_length_c                   11.3748(14)
_cell_measurement_reflns_used    3041
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.88
_cell_volume                     872.40(18)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9725
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.9709
_exptl_absorpt_correction_T_min  0.9462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0362
_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)+(0.0524P)²+0.2114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                3253
_reflns_number_total             3926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b301578e.txt
_cod_data_source_block           02258a
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7103797
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.29292(15) 0.01687(15) 0.38994(13) 0.0252(3) Uani 1 1 d . . .
C2 C 0.24710(15) 0.17605(15) 0.31235(13) 0.0249(3) Uani 1 1 d . . .
C3 C 0.27332(16) 0.17424(16) 0.17748(13) 0.0290(3) Uani 1 1 d . . .
H3A H 0.2172 0.2567 0.1183 0.035 Uiso 1 1 calc R . .
C4 C 0.44500(17) 0.16678(18) 0.13131(14) 0.0339(3) Uani 1 1 d . . .
H4A H 0.4952 0.2462 0.1484 0.041 Uiso 1 1 calc R . .
H4B H 0.4698 0.1825 0.0389 0.041 Uiso 1 1 calc R . .
C5 C 0.49173(17) 0.00047(18) 0.21083(14) 0.0337(3) Uani 1 1 d . . .
H5A H 0.5368 -0.0606 0.1550 0.040 Uiso 1 1 calc R . .
H5B H 0.5643 0.0035 0.2636 0.040 Uiso 1 1 calc R . .
C6 C 0.34213(16) -0.06841(16) 0.29509(14) 0.0297(3) Uani 1 1 d . . .
H6A H 0.3414 -0.1844 0.3324 0.036 Uiso 1 1 calc R . .
C7 C 0.23260(18) 0.00632(17) 0.20225(15) 0.0339(3) Uani 1 1 d . . .
H7A H 0.2572 -0.0231 0.1244 0.041 Uiso 1 1 calc R . .
H7B H 0.1264 -0.0152 0.2433 0.041 Uiso 1 1 calc R . .
C8 C 0.28120(15) -0.03504(16) 0.51664(13) 0.0264(3) Uani 1 1 d . . .
H8A H 0.2468 0.0388 0.5584 0.032 Uiso 1 1 calc R . .
C9 C 0.31512(15) -0.19246(16) 0.59891(13) 0.0253(3) Uani 1 1 d . . .
C10 C 0.43731(15) -0.28613(16) 0.57141(13) 0.0258(3) Uani 1 1 d . . .
F10 F 0.53898(9) -0.23312(10) 0.46464(8) 0.0329(2) Uani 1 1 d . . .
C11 C 0.46163(16) -0.43471(16) 0.65219(14) 0.0300(3) Uani 1 1 d . . .
F11 F 0.58060(10) -0.52021(10) 0.62010(9) 0.0404(2) Uani 1 1 d . . .
C12 C 0.36346(18) -0.49444(16) 0.76563(14) 0.0327(3) Uani 1 1 d . . .
F12 F 0.38414(13) -0.63939(10) 0.84261(9) 0.0473(3) Uani 1 1 d . . .
C13 C 0.24306(17) -0.40447(17) 0.79858(13) 0.0309(3) Uani 1 1 d . . .
F13 F 0.14569(11) -0.46294(12) 0.90767(8) 0.0429(2) Uani 1 1 d . . .
C14 C 0.22116(15) -0.25643(17) 0.71657(13) 0.0280(3) Uani 1 1 d . . .
F14 F 0.10152(10) -0.17345(11) 0.75140(8) 0.0384(2) Uani 1 1 d . . .
C15 C 0.18666(15) 0.28790(16) 0.35878(13) 0.0264(3) Uani 1 1 d . . .
H15A H 0.1801 0.2655 0.4477 0.032 Uiso 1 1 calc R . .
C16 C 0.12909(15) 0.44180(15) 0.28793(13) 0.0245(3) Uani 1 1 d . . .
C17 C 0.20074(15) 0.54235(16) 0.17189(13) 0.0258(3) Uani 1 1 d . . .
F17 F 0.33573(9) 0.50335(10) 0.11586(8) 0.0348(2) Uani 1 1 d . . .
C18 C 0.14064(16) 0.68686(16) 0.11146(13) 0.0278(3) Uani 1 1 d . . .
F18 F 0.21394(10) 0.77914(10) 0.00000(8) 0.0380(2) Uani 1 1 d . . .
C19 C 0.00547(16) 0.73684(16) 0.16691(14) 0.0288(3) Uani 1 1 d . . .
F19 F -0.05455(11) 0.87519(10) 0.10915(9) 0.0427(2) Uani 1 1 d . . .
C20 C -0.06686(15) 0.64302(16) 0.28371(13) 0.0278(3) Uani 1 1 d . . .
F20 F -0.19745(10) 0.69155(11) 0.33906(9) 0.0389(2) Uani 1 1 d . . .
C21 C -0.00578(15) 0.49943(16) 0.34116(12) 0.0253(3) Uani 1 1 d . . .
F21 F -0.08192(10) 0.41034(10) 0.45399(8) 0.0331(2) 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'
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
_geom_angle_publ_flag
C8 C1 C2 125.16(12) . . ?
C8 C1 C6 129.90(13) . . ?
C2 C1 C6 104.81(11) . . ?
C15 C2 C1 125.31(12) . . ?
C15 C2 C3 129.57(12) . . ?
C1 C2 C3 104.97(11) . . ?
C2 C3 C7 100.45(11) . . ?
C2 C3 C4 107.24(11) . . ?
C7 C3 C4 100.98(12) . . ?
C2 C3 H3A 115.4 . . ?
C7 C3 H3A 115.4 . . ?
C4 C3 H3A 115.4 . . ?
C3 C4 C5 103.56(12) . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4B 111.0 . . ?
C5 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C6 C5 C4 103.33(11) . . ?
C6 C5 H5A 111.1 . . ?
C4 C5 H5A 111.1 . . ?
C6 C5 H5B 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
C1 C6 C7 100.29(11) . . ?
C1 C6 C5 107.49(11) . . ?
C7 C6 C5 100.79(12) . . ?
C1 C6 H6A 115.4 . . ?
C7 C6 H6A 115.4 . . ?
C5 C6 H6A 115.4 . . ?
C3 C7 C6 94.88(11) . . ?
C3 C7 H7A 112.8 . . ?
C6 C7 H7A 112.8 . . ?
C3 C7 H7B 112.8 . . ?
C6 C7 H7B 112.8 . . ?
H7A C7 H7B 110.2 . . ?
C1 C8 C9 127.71(13) . . ?
C1 C8 H8A 116.1 . . ?
C9 C8 H8A 116.1 . . ?
C10 C9 C14 115.36(13) . . ?
C10 C9 C8 125.47(13) . . ?
C14 C9 C8 119.16(12) . . ?
F10 C10 C11 116.99(12) . . ?
F10 C10 C9 120.36(12) . . ?
C11 C10 C9 122.64(13) . . ?
F11 C11 C12 120.14(13) . . ?
F11 C11 C10 120.01(14) . . ?
C12 C11 C10 119.86(13) . . ?
F12 C12 C13 120.23(14) . . ?
F12 C12 C11 120.16(14) . . ?
C13 C12 C11 119.60(13) . . ?
F13 C13 C12 119.86(13) . . ?
F13 C13 C14 120.58(14) . . ?
C12 C13 C14 119.53(13) . . ?
F14 C14 C13 117.66(13) . . ?
F14 C14 C9 119.35(12) . . ?
C13 C14 C9 122.96(13) . . ?
C2 C15 C16 127.36(12) . . ?
C2 C15 H15A 116.3 . . ?
C16 C15 H15A 116.3 . . ?
C17 C16 C21 115.06(12) . . ?
C17 C16 C15 125.83(12) . . ?
C21 C16 C15 119.04(12) . . ?
F17 C17 C18 117.03(12) . . ?
F17 C17 C16 120.28(12) . . ?
C18 C17 C16 122.65(12) . . ?
F18 C18 C19 119.73(12) . . ?
F18 C18 C17 120.34(13) . . ?
C19 C18 C17 119.92(13) . . ?
F19 C19 C18 120.58(13) . . ?
F19 C19 C20 120.11(13) . . ?
C18 C19 C20 119.30(13) . . ?
F20 C20 C21 120.61(13) . . ?
F20 C20 C19 119.70(12) . . ?
C21 C20 C19 119.68(12) . . ?
F21 C21 C20 117.64(12) . . ?
F21 C21 C16 119.02(12) . . ?
C20 C21 C16 123.33(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C8 1.3359(19) . ?
C1 C2 1.4915(18) . ?
C1 C6 1.5145(19) . ?
C2 C15 1.3341(19) . ?
C2 C3 1.5086(19) . ?
C3 C7 1.536(2) . ?
C3 C4 1.547(2) . ?
C3 H3A 1.0000 . ?
C4 C5 1.550(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.544(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5435(19) . ?
C6 H6A 1.0000 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.4668(18) . ?
C8 H8A 0.9500 . ?
C9 C10 1.3893(19) . ?
C9 C14 1.395(2) . ?
C10 F10 1.3348(16) . ?
C10 C11 1.381(2) . ?
C11 F11 1.3385(16) . ?
C11 C12 1.376(2) . ?
C12 F12 1.3348(16) . ?
C12 C13 1.375(2) . ?
C13 F13 1.3378(17) . ?
C13 C14 1.378(2) . ?
C14 F14 1.3388(16) . ?
C15 C16 1.4691(18) . ?
C15 H15A 0.9500 . ?
C16 C17 1.391(2) . ?
C16 C21 1.3938(18) . ?
C17 F17 1.3395(16) . ?
C17 C18 1.3824(19) . ?
C18 F18 1.3360(16) . ?
C18 C19 1.376(2) . ?
C19 F19 1.3325(16) . ?
C19 C20 1.377(2) . ?
C20 F20 1.3382(15) . ?
C20 C21 1.3717(19) . ?
C21 F21 1.3455(16) . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C1 C2 C15 -0.8(2) . . . . ?
C6 C1 C2 C15 175.43(13) . . . . ?
C8 C1 C2 C3 -176.59(13) . . . . ?
C6 C1 C2 C3 -0.40(14) . . . . ?
C15 C2 C3 C7 -140.59(15) . . . . ?
C1 C2 C3 C7 34.99(13) . . . . ?
C15 C2 C3 C4 114.34(16) . . . . ?
C1 C2 C3 C4 -70.08(13) . . . . ?
C2 C3 C4 C5 69.99(14) . . . . ?
C7 C3 C4 C5 -34.71(13) . . . . ?
C3 C4 C5 C6 -0.71(14) . . . . ?
C8 C1 C6 C7 141.82(15) . . . . ?
C2 C1 C6 C7 -34.13(14) . . . . ?
C8 C1 C6 C5 -113.30(16) . . . . ?
C2 C1 C6 C5 70.75(13) . . . . ?
C4 C5 C6 C1 -68.84(14) . . . . ?
C4 C5 C6 C7 35.68(13) . . . . ?
C2 C3 C7 C6 -54.33(12) . . . . ?
C4 C3 C7 C6 55.72(12) . . . . ?
C1 C6 C7 C3 53.97(13) . . . . ?
C5 C6 C7 C3 -56.24(13) . . . . ?
C2 C1 C8 C9 175.75(13) . . . . ?
C6 C1 C8 C9 0.5(2) . . . . ?
C1 C8 C9 C10 41.2(2) . . . . ?
C1 C8 C9 C14 -140.23(15) . . . . ?
C14 C9 C10 F10 -176.28(11) . . . . ?
C8 C9 C10 F10 2.4(2) . . . . ?
C14 C9 C10 C11 2.43(19) . . . . ?
C8 C9 C10 C11 -178.90(13) . . . . ?
F10 C10 C11 F11 -1.91(19) . . . . ?
C9 C10 C11 F11 179.35(12) . . . . ?
F10 C10 C11 C12 178.03(12) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
F11 C11 C12 F12 -1.8(2) . . . . ?
C10 C11 C12 F12 178.26(12) . . . . ?
F11 C11 C12 C13 178.88(12) . . . . ?
C10 C11 C12 C13 -1.1(2) . . . . ?
F12 C12 C13 F13 -0.5(2) . . . . ?
C11 C12 C13 F13 178.78(12) . . . . ?
F12 C12 C13 C14 -178.37(12) . . . . ?
C11 C12 C13 C14 0.9(2) . . . . ?
F13 C13 C14 F14 1.3(2) . . . . ?
C12 C13 C14 F14 179.11(12) . . . . ?
F13 C13 C14 C9 -176.88(12) . . . . ?
C12 C13 C14 C9 0.9(2) . . . . ?
C10 C9 C14 F14 179.31(11) . . . . ?
C8 C9 C14 F14 0.55(19) . . . . ?
C10 C9 C14 C13 -2.5(2) . . . . ?
C8 C9 C14 C13 178.69(12) . . . . ?
C1 C2 C15 C16 -174.87(13) . . . . ?
C3 C2 C15 C16 -0.1(2) . . . . ?
C2 C15 C16 C17 -45.9(2) . . . . ?
C2 C15 C16 C21 137.17(15) . . . . ?
C21 C16 C17 F17 175.75(11) . . . . ?
C15 C16 C17 F17 -1.3(2) . . . . ?
C21 C16 C17 C18 -2.01(19) . . . . ?
C15 C16 C17 C18 -179.02(12) . . . . ?
F17 C17 C18 F18 2.19(19) . . . . ?
C16 C17 C18 F18 -179.98(12) . . . . ?
F17 C17 C18 C19 -177.08(12) . . . . ?
C16 C17 C18 C19 0.7(2) . . . . ?
F18 C18 C19 F19 1.4(2) . . . . ?
C17 C18 C19 F19 -179.32(12) . . . . ?
F18 C18 C19 C20 -177.92(12) . . . . ?
C17 C18 C19 C20 1.4(2) . . . . ?
F19 C19 C20 F20 -0.2(2) . . . . ?
C18 C19 C20 F20 179.17(12) . . . . ?
F19 C19 C20 C21 178.62(12) . . . . ?
C18 C19 C20 C21 -2.0(2) . . . . ?
F20 C20 C21 F21 0.15(19) . . . . ?
C19 C20 C21 F21 -178.62(12) . . . . ?
F20 C20 C21 C16 179.46(12) . . . . ?
C19 C20 C21 C16 0.7(2) . . . . ?
C17 C16 C21 F21 -179.40(11) . . . . ?
C15 C16 C21 F21 -2.17(18) . . . . ?
C17 C16 C21 C20 1.30(19) . . . . ?
C15 C16 C21 C20 178.53(12) . . . . ?
