#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/69/2216900.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_2216900
loop_
_publ_author_name
'Wu Zhang'
'Li Yao'
'Ruo-Jie Tao'
_publ_section_title
;
 4,4'-Bis(prop-2-ynyloxy)biphenyl
;
_journal_coeditor_code           BH2156
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o307
_journal_page_last               o307
_journal_paper_doi               10.1107/S160053680706638X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C18 H14 O2'
_chemical_formula_moiety         'C18 H14 O2'
_chemical_formula_sum            'C18 H14 O2'
_chemical_formula_weight         262.29
_chemical_name_systematic
;
4,4'-Bis(prop-2-ynyloxy)biphenyl
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5881(16)
_cell_length_b                   8.2061(18)
_cell_length_c                   22.873(5)
_cell_measurement_reflns_used    1896
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.823
_cell_measurement_theta_min      5.366
_cell_volume                     1424.3(5)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics
;
SHELXTL (Bruker, 2005) and DIAMOND (Brandenburg,
1998)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_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  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7569
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.22
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0510
_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)+(0.0448P)²+0.3393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                1037
_reflns_number_total             1392
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2156.cif
_cod_data_source_block           I
_cod_database_code               2216900
_cod_database_fobs_code          2216900
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
C C1 0.0440(4) 0.7955(3) 0.21976(10) 0.0956(9) Uani d . 1
H H1 0.0256 0.8708 0.2495 0.115 Uiso calc R 1
C C2 0.0669(3) 0.7021(2) 0.18279(8) 0.0636(5) Uani d . 1
C C3 0.0975(3) 0.5881(2) 0.13510(8) 0.0587(5) Uani d . 1
H H3A 0.0660 0.6382 0.0981 0.070 Uiso calc R 1
H H3B 0.2212 0.5586 0.1336 0.070 Uiso calc R 1
C C4 0.0023(2) 0.32626(19) 0.10298(7) 0.0408(4) Uani d . 1
C C5 -0.0877(2) 0.1838(2) 0.11486(7) 0.0474(4) Uani d . 1
H H5A -0.1484 0.1728 0.1500 0.057 Uiso calc R 1
C C6 -0.0879(2) 0.0580(2) 0.07515(7) 0.0465(4) Uani d . 1
H H6A -0.1493 -0.0369 0.0842 0.056 Uiso calc R 1
C C7 0.0007(2) 0.06755(18) 0.02165(6) 0.0381(4) Uani d . 1
C C8 0.0918(2) 0.2113(2) 0.01155(7) 0.0483(5) Uani d . 1
H H8A 0.1545 0.2222 -0.0232 0.058 Uiso calc R 1
C C9 0.0934(2) 0.3391(2) 0.05092(7) 0.0493(5) Uani d . 1
H H9A 0.1558 0.4337 0.0424 0.059 Uiso calc R 1
O O1 -0.00711(15) 0.44653(14) 0.14459(5) 0.0507(4) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.139(3) 0.0774(17) 0.0706(14) -0.0022(17) 0.0079(14) -0.0255(13)
C2 0.0802(14) 0.0552(12) 0.0554(11) -0.0051(11) 0.0010(10) -0.0046(10)
C3 0.0691(13) 0.0485(11) 0.0586(11) -0.0098(10) 0.0079(10) -0.0049(9)
C4 0.0390(9) 0.0414(9) 0.0421(8) 0.0028(8) -0.0008(7) 0.0011(7)
C5 0.0483(10) 0.0518(11) 0.0421(9) -0.0054(8) 0.0082(8) 0.0036(8)
C6 0.0485(10) 0.0439(10) 0.0470(9) -0.0094(8) 0.0049(8) 0.0042(8)
C7 0.0323(8) 0.0388(9) 0.0431(8) 0.0033(7) -0.0009(7) 0.0052(7)
C8 0.0523(10) 0.0459(10) 0.0468(9) -0.0057(8) 0.0132(8) 0.0021(8)
C9 0.0541(11) 0.0407(10) 0.0531(10) -0.0093(8) 0.0111(8) 0.0018(8)
O1 0.0577(8) 0.0463(7) 0.0480(6) -0.0062(6) 0.0081(6) -0.0044(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'
O O 0.0106 0.0060 '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_3
_geom_angle
C2 C1 H1 . 180.0
C1 C2 C3 . 178.3(2)
O1 C3 C2 . 108.71(15)
O1 C3 H3A . 109.9
C2 C3 H3A . 109.9
O1 C3 H3B . 109.9
C2 C3 H3B . 109.9
H3A C3 H3B . 108.3
O1 C4 C5 . 116.53(14)
O1 C4 C9 . 124.67(15)
C5 C4 C9 . 118.80(15)
C6 C5 C4 . 120.43(15)
C6 C5 H5A . 119.8
C4 C5 H5A . 119.8
C5 C6 C7 . 122.35(15)
C5 C6 H6A . 118.8
C7 C6 H6A . 118.8
C8 C7 C6 . 115.68(14)
C8 C7 C7 5 121.82(17)
C6 C7 C7 5 122.50(17)
C9 C8 C7 . 122.78(15)
C9 C8 H8A . 118.6
C7 C8 H8A . 118.6
C4 C9 C8 . 119.95(15)
C4 C9 H9A . 120.0
C8 C9 H9A . 120.0
C4 O1 C3 . 116.87(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.155(3)
C1 H1 . 0.9300
C2 C3 . 1.456(3)
C3 O1 . 1.424(2)
C3 H3A . 0.9700
C3 H3B . 0.9700
C4 O1 . 1.3729(19)
C4 C5 . 1.381(2)
C4 C9 . 1.381(2)
C5 C6 . 1.375(2)
C5 H5A . 0.9300
C6 C7 . 1.399(2)
C6 H6A . 0.9300
C7 C8 . 1.386(2)
C7 C7 5 1.487(3)
C8 C9 . 1.382(2)
C8 H8A . 0.9300
C9 H9A . 0.9300
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_4
_geom_torsion
O1 C4 C5 C6 . . 178.87(15)
C9 C4 C5 C6 . . -0.8(2)
C4 C5 C6 C7 . . -0.1(3)
C5 C6 C7 C8 . . 1.1(2)
C5 C6 C7 C7 . 5 -179.38(18)
C6 C7 C8 C9 . . -1.2(2)
C7 C7 C8 C9 5 . 179.30(18)
O1 C4 C9 C8 . . -178.91(16)
C5 C4 C9 C8 . . 0.7(3)
C7 C8 C9 C4 . . 0.3(3)
C5 C4 O1 C3 . . 174.67(16)
C9 C4 O1 C3 . . -5.7(2)
C2 C3 O1 C4 . . 178.71(15)
