#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/05/2230590.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230590
loop_
_publ_author_name
'Zhao, Baohai'
'Lin, Jimao'
'Zhao, Cuihua'
'Wang, Ziying'
_publ_section_title
;
 1,4-Dimethoxy-2,5-bis{2-[4-(trifluoromethyl)phenyl]ethynyl}benzene
;
_journal_coeditor_code           CV5093
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1601
_journal_paper_doi               10.1107/S160053681102099X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C26 H16 F6 O2'
_chemical_formula_moiety         'C26 H16 F6 O2'
_chemical_formula_sum            'C26 H16 F6 O2'
_chemical_formula_weight         474.39
_chemical_name_systematic
;
1,4-Dimethoxy-2,5-bis{2-[4-(trifluoromethyl)phenyl]ethynyl}benzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.467(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.1473(4)
_cell_length_b                   13.0795(6)
_cell_length_c                   7.5875(4)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.41
_cell_volume                     1096.88(9)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9899
_diffrn_reflns_theta_full        27.38
_diffrn_reflns_theta_max         27.38
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.9767
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.211
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0422
_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)+(0.0488P)²+0.2350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1172
_reflns_number_gt                1753
_reflns_number_total             2484
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv5093.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230590
_cod_database_fobs_code          2230590
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.75647(18) 0.83209(17) 0.5592(3) 0.0718(6) Uani d D 1 1 . .
C C2 0.63855(14) 0.85402(14) 0.6275(2) 0.0527(4) Uani d . 1 1 A .
C C3 0.54917(16) 0.78099(15) 0.6153(3) 0.0588(5) Uani d . 1 1 . .
H H3 0.5617 0.7178 0.5647 0.071 Uiso calc R 1 1 A .
C C4 0.44076(15) 0.80134(14) 0.6781(2) 0.0562(5) Uani d . 1 1 A .
H H4 0.3805 0.7518 0.6697 0.067 Uiso calc R 1 1 . .
C C5 0.42165(13) 0.89548(14) 0.7537(2) 0.0473(4) Uani d . 1 1 . .
C C6 0.51220(16) 0.96868(14) 0.7635(3) 0.0589(5) Uani d . 1 1 A .
H H6 0.4999 1.0322 0.8131 0.071 Uiso calc R 1 1 . .
C C7 0.62038(16) 0.94824(15) 0.7003(3) 0.0608(5) Uani d . 1 1 . .
H H7 0.6806 0.9978 0.7069 0.073 Uiso calc R 1 1 A .
C C8 0.31058(14) 0.91755(14) 0.8243(2) 0.0525(4) Uani d . 1 1 A .
C C9 0.22045(14) 0.93931(13) 0.8846(2) 0.0497(4) Uani d . 1 1 . .
C C10 0.10877(13) 0.96910(12) 0.9454(2) 0.0452(4) Uani d . 1 1 A .
C C11 0.03456(14) 1.03921(12) 0.8455(2) 0.0477(4) Uani d . 1 1 . .
H H11 0.0584 1.0656 0.7417 0.057 Uiso calc R 1 1 A .
C C12 0.07381(13) 0.92971(12) 1.1021(2) 0.0455(4) Uani d . 1 1 . .
C C13 0.1199(2) 0.82346(18) 1.3576(3) 0.0769(6) Uani d . 1 1 . .
H H13A 0.1109 0.8791 1.4372 0.115 Uiso calc R 1 1 A .
H H13B 0.1823 0.7782 1.4105 0.115 Uiso calc R 1 1 . .
H H13C 0.0449 0.7867 1.3348 0.115 Uiso calc R 1 1 . .
O O1 0.15207(10) 0.86246(10) 1.19450(17) 0.0605(4) Uani d . 1 1 A .
F F1 0.7461(6) 0.8553(4) 0.3877(5) 0.0928(16) Uani d PD 0.530(10) 1 A 1
F F2 0.8484(5) 0.8832(9) 0.6296(14) 0.183(5) Uani d PD 0.530(10) 1 A 1
F F3 0.7807(6) 0.7351(3) 0.5523(9) 0.125(3) Uani d PD 0.530(10) 1 A 1
F F1' 0.7695(6) 0.7396(4) 0.5079(11) 0.136(4) Uani d PD 0.470(10) 1 A 2
F F2' 0.8458(4) 0.8398(6) 0.6905(7) 0.0953(18) Uani d PD 0.470(10) 1 A 2
F F3' 0.7830(9) 0.8979(10) 0.4453(17) 0.205(6) Uani d PD 0.470(10) 1 A 2
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F2 C1 F3' . . 71.9(5) ?
F2 C1 F1' . . 120.1(5) ?
F3' C1 F1' . . 112.5(6) ?
F2 C1 F3 . . 111.5(5) ?
F3' C1 F3 . . 124.1(6) ?
F1' C1 F3 . . 15.5(5) ?
F2 C1 F2' . . 32.8(6) ?
F3' C1 F2' . . 103.9(7) ?
F1' C1 F2' . . 101.3(4) ?
F3 C1 F2' . . 87.9(5) ?
F2 C1 F1 . . 104.7(6) ?
F3' C1 F1 . . 35.2(8) ?
F1' C1 F1 . . 85.2(4) ?
F3 C1 F1 . . 100.1(4) ?
F2' C1 F1 . . 133.2(3) ?
F2 C1 C2 . . 116.4(3) ?
F3' C1 C2 . . 113.2(3) ?
F1' C1 C2 . . 115.0(4) ?
F3 C1 C2 . . 113.4(3) ?
F2' C1 C2 . . 109.5(3) ?
F1 C1 C2 . . 109.1(3) ?
C3 C2 C7 . . 120.41(15) ?
C3 C2 C1 . . 120.20(17) ?
C7 C2 C1 . . 119.38(17) ?
C2 C3 C4 . . 120.11(17) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C3 C4 C5 . . 120.14(17) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C6 C5 C4 . . 119.06(14) ?
C6 C5 C8 . . 119.78(16) ?
C4 C5 C8 . . 121.15(16) ?
C7 C6 C5 . . 120.70(17) ?
C7 C6 H6 . . 119.6 ?
C5 C6 H6 . . 119.6 ?
C2 C7 C6 . . 119.57(17) ?
C2 C7 H7 . . 120.2 ?
C6 C7 H7 . . 120.2 ?
C9 C8 C5 . . 177.5(2) ?
C8 C9 C10 . . 175.89(19) ?
C11 C10 C12 . . 119.64(13) ?
C11 C10 C9 . . 118.86(14) ?
C12 C10 C9 . . 121.50(15) ?
C12 C11 C10 3_577 . 121.18(15) ?
C12 C11 H11 3_577 . 119.4 ?
C10 C11 H11 . . 119.4 ?
O1 C12 C11 . 3_577 124.45(15) ?
O1 C12 C10 . . 116.37(13) ?
C11 C12 C10 3_577 . 119.18(15) ?
O1 C13 H13A . . 109.5 ?
O1 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O1 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C12 O1 C13 . . 117.37(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 F2 . 1.281(4) ?
C1 F3' . 1.281(4) ?
C1 F1' . 1.285(4) ?
C1 F3 . 1.300(4) ?
C1 F2' . 1.318(4) ?
C1 F1 . 1.327(4) ?
C1 C2 . 1.502(2) ?
C2 C3 . 1.375(3) ?
C2 C7 . 1.376(3) ?
C3 C4 . 1.381(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.386(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.386(2) ?
C5 C8 . 1.441(2) ?
C6 C7 . 1.380(2) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.191(2) ?
C9 C10 . 1.437(2) ?
C10 C11 . 1.391(2) ?
C10 C12 . 1.397(2) ?
C11 C12 3_577 1.381(2) ?
C11 H11 . 0.9300 ?
C12 O1 . 1.3664(19) ?
C12 C11 3_577 1.381(2) ?
C13 O1 . 1.427(2) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
F2 C1 C2 C3 . . . . -154.8(8) ?
F3' C1 C2 C3 . . . . 124.7(9) ?
F1' C1 C2 C3 . . . . -6.6(5) ?
F3 C1 C2 C3 . . . . -23.5(4) ?
F2' C1 C2 C3 . . . . -119.9(4) ?
F1 C1 C2 C3 . . . . 87.1(3) ?
F2 C1 C2 C7 . . . . 26.0(8) ?
F3' C1 C2 C7 . . . . -54.5(10) ?
F1' C1 C2 C7 . . . . 174.2(5) ?
F3 C1 C2 C7 . . . . 157.3(4) ?
F2' C1 C2 C7 . . . . 60.9(4) ?
F1 C1 C2 C7 . . . . -92.1(3) ?
C7 C2 C3 C4 . . . . -0.8(3) ?
C1 C2 C3 C4 . . . . -179.95(18) ?
C2 C3 C4 C5 . . . . 0.0(3) ?
C3 C4 C5 C6 . . . . 0.6(3) ?
C3 C4 C5 C8 . . . . -178.37(17) ?
C4 C5 C6 C7 . . . . -0.5(3) ?
C8 C5 C6 C7 . . . . 178.50(18) ?
C3 C2 C7 C6 . . . . 0.9(3) ?
C1 C2 C7 C6 . . . . -179.94(18) ?
C5 C6 C7 C2 . . . . -0.3(3) ?
C6 C5 C8 C9 . . . . -1(5) ?
C4 C5 C8 C9 . . . . 18E1(10) ?
C5 C8 C9 C10 . . . . 85(5) ?
C8 C9 C10 C11 . . . . -11(3) ?
C8 C9 C10 C12 . . . . 169(3) ?
C12 C10 C11 C12 . . . 3_577 -0.4(3) ?
C9 C10 C11 C12 . . . 3_577 179.90(16) ?
C11 C10 C12 O1 . . . . -179.04(15) ?
C9 C10 C12 O1 . . . . 0.6(2) ?
C11 C10 C12 C11 . . . 3_577 0.4(3) ?
C9 C10 C12 C11 . . . 3_577 -179.92(16) ?
C11 C12 O1 C13 3_577 . . . -1.1(3) ?
C10 C12 O1 C13 . . . . 178.26(17) ?
