#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/53/2225394.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_2225394
loop_
_publ_author_name
'Sundar, J. Kalyana'
'Kumar, K. Mohan'
'Vijayakumar, V.'
'Suresh, J.'
'Natarajan, S.'
'Lakshman, P. L. Nilantha'
_publ_section_title
;
 (E)-1,1,4,4-Tetraphenylbut-2-yne-1,4-diol
;
_journal_coeditor_code           TK2631
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o679
_journal_paper_doi               10.1107/S160053681000629X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C28 H22 O2'
_chemical_formula_moiety         'C28 H22 O2'
_chemical_formula_sum            'C28 H22 O2'
_chemical_formula_weight         390.46
_chemical_name_systematic
;
(E)-1,1,4,4-Tetraphenylbut-2-yne-1,4-diol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 104.930(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.7760(7)
_cell_length_b                   6.1154(4)
_cell_length_c                   14.7620(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     1027.20(12)
_computing_cell_refinement       'CAD-4 Express (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 Express (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1996)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (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  'Nonius Mach3'
_diffrn_measurement_method       ω-2θ
_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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2268
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.56
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_correction_T_min  0.9823
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1793
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0523
_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)+(0.191P)²+0.1322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1884
_refine_ls_wR_factor_ref         0.2762
_reflns_number_gt                1190
_reflns_number_total             1793
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2631.cif
_cod_data_source_block           I
_cod_original_cell_volume        1027.20(11)
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2225394
_cod_database_fobs_code          2225394
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_disorder_assembly
_atom_site_disorder_group
C C14 0.4922(3) 0.4489(5) 0.03168(19) 0.0503(8) Uani d . 1 . .
O O1 0.5081(2) 0.0924(4) 0.09705(15) 0.0718(9) Uani d . 1 . .
H H1A 0.4679 0.0450 0.0471 0.108 Uiso calc R 1 . .
C C12 0.5499(2) 0.3958(5) 0.20504(18) 0.0443(8) Uani d . 1 . .
C C13 0.4735(3) 0.3145(5) 0.10995(18) 0.0471(8) Uani d . 1 . .
C C11 0.5673(3) 0.2553(6) 0.2819(2) 0.0619(9) Uani d . 1 . .
H H11 0.5343 0.1162 0.2752 0.074 Uiso calc R 1 . .
C C6 0.3446(3) 0.3186(5) 0.11176(17) 0.0496(8) Uani d . 1 . .
C C7 0.5985(3) 0.5994(5) 0.2167(2) 0.0569(9) Uani d . 1 . .
H H7 0.5862 0.6945 0.1659 0.068 Uiso calc R 1 . .
C C1 0.2929(4) 0.1361(7) 0.1416(2) 0.0754(12) Uani d . 1 . .
H H1 0.3356 0.0079 0.1585 0.090 Uiso calc R 1 . .
C C5 0.2780(3) 0.5067(6) 0.0880(2) 0.0605(9) Uani d . 1 . .
H H5 0.3123 0.6296 0.0690 0.073 Uiso calc R 1 . .
C C9 0.6848(3) 0.5280(7) 0.3798(2) 0.0707(11) Uani d . 1 . .
H H9 0.7307 0.5718 0.4381 0.085 Uiso calc R 1 . .
C C10 0.6348(3) 0.3262(7) 0.3685(2) 0.0742(11) Uani d . 1 . .
H H10 0.6459 0.2334 0.4199 0.089 Uiso calc R 1 . .
C C8 0.6667(3) 0.6660(7) 0.3044(3) 0.0681(10) Uani d . 1 . .
H H8 0.6999 0.8049 0.3116 0.082 Uiso calc R 1 . .
C C4 0.1615(3) 0.5167(8) 0.0917(3) 0.0861(14) Uani d . 1 . .
H H4 0.1181 0.6442 0.0749 0.103 Uiso calc R 1 . .
C C2 0.1750(5) 0.1500(11) 0.1458(3) 0.0978(17) Uani d . 1 . .
H H2 0.1398 0.0299 0.1660 0.117 Uiso calc R 1 . .
C C3 0.1116(4) 0.3374(12) 0.1204(3) 0.1031(19) Uani d . 1 . .
H H3 0.0335 0.3425 0.1228 0.124 Uiso calc R 1 . .
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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 C14 C13 3_665 . 178.3(4) ?
C13 O1 H1A . . 109.5 ?
C7 C12 C11 . . 119.4(3) ?
C7 C12 C13 . . 122.5(2) ?
C11 C12 C13 . . 118.1(3) ?
O1 C13 C14 . . 108.4(2) ?
O1 C13 C6 . . 109.5(3) ?
C14 C13 C6 . . 110.7(2) ?
O1 C13 C12 . . 107.7(2) ?
C14 C13 C12 . . 111.3(2) ?
C6 C13 C12 . . 109.2(2) ?
C10 C11 C12 . . 119.0(3) ?
C10 C11 H11 . . 120.5 ?
C12 C11 H11 . . 120.5 ?
C5 C6 C1 . . 118.7(3) ?
C5 C6 C13 . . 120.7(3) ?
C1 C6 C13 . . 120.6(3) ?
C12 C7 C8 . . 120.4(3) ?
C12 C7 H7 . . 119.8 ?
C8 C7 H7 . . 119.8 ?
C6 C1 C2 . . 118.7(5) ?
C6 C1 H1 . . 120.6 ?
C2 C1 H1 . . 120.6 ?
C6 C5 C4 . . 121.8(4) ?
C6 C5 H5 . . 119.1 ?
C4 C5 H5 . . 119.1 ?
C10 C9 C8 . . 119.2(3) ?
C10 C9 H9 . . 120.4 ?
C8 C9 H9 . . 120.4 ?
C9 C10 C11 . . 121.6(3) ?
C9 C10 H10 . . 119.2 ?
C11 C10 H10 . . 119.2 ?
C9 C8 C7 . . 120.4(3) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C3 C4 C5 . . 119.1(5) ?
C3 C4 H4 . . 120.5 ?
C5 C4 H4 . . 120.5 ?
C3 C2 C1 . . 120.9(4) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C4 C3 C2 . . 120.8(4) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
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
C14 C14 3_665 1.178(5) ?
C14 C13 . 1.480(4) ?
O1 C13 . 1.445(3) ?
O1 H1A . 0.8200 ?
C12 C7 . 1.363(4) ?
C12 C11 . 1.395(4) ?
C12 C13 . 1.541(4) ?
C13 C6 . 1.526(4) ?
C11 C10 . 1.389(5) ?
C11 H11 . 0.9300 ?
C6 C5 . 1.385(5) ?
C6 C1 . 1.395(5) ?
C7 C8 . 1.396(5) ?
C7 H7 . 0.9300 ?
C1 C2 . 1.408(7) ?
C1 H1 . 0.9300 ?
C5 C4 . 1.389(5) ?
C5 H5 . 0.9300 ?
C9 C10 . 1.359(5) ?
C9 C8 . 1.370(5) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C8 H8 . 0.9300 ?
C4 C3 . 1.362(7) ?
C4 H4 . 0.9300 ?
C2 C3 . 1.366(7) ?
C2 H2 . 0.9300 ?
C3 H3 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1a O1 3_655 0.82 2.37 3.040(3) 139
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
C14 C14 C13 O1 3_665 . . . 7(15) ?
C14 C14 C13 C6 3_665 . . . -114(15) ?
C14 C14 C13 C12 3_665 . . . 125(15) ?
C7 C12 C13 O1 . . . . 137.1(3) ?
C11 C12 C13 O1 . . . . -44.2(3) ?
C7 C12 C13 C14 . . . . 18.4(4) ?
C11 C12 C13 C14 . . . . -162.8(3) ?
C7 C12 C13 C6 . . . . -104.1(3) ?
C11 C12 C13 C6 . . . . 74.7(3) ?
C7 C12 C11 C10 . . . . -0.5(5) ?
C13 C12 C11 C10 . . . . -179.3(3) ?
O1 C13 C6 C5 . . . . -155.4(2) ?
C14 C13 C6 C5 . . . . -36.0(4) ?
C12 C13 C6 C5 . . . . 86.8(3) ?
O1 C13 C6 C1 . . . . 27.6(3) ?
C14 C13 C6 C1 . . . . 147.0(3) ?
C12 C13 C6 C1 . . . . -90.2(3) ?
C11 C12 C7 C8 . . . . 1.0(5) ?
C13 C12 C7 C8 . . . . 179.7(3) ?
C5 C6 C1 C2 . . . . 0.4(5) ?
C13 C6 C1 C2 . . . . 177.5(3) ?
C1 C6 C5 C4 . . . . -1.0(5) ?
C13 C6 C5 C4 . . . . -178.1(3) ?
C8 C9 C10 C11 . . . . 1.1(6) ?
C12 C11 C10 C9 . . . . -0.6(6) ?
C10 C9 C8 C7 . . . . -0.6(5) ?
C12 C7 C8 C9 . . . . -0.4(5) ?
C6 C5 C4 C3 . . . . 0.6(5) ?
C6 C1 C2 C3 . . . . 0.5(6) ?
C5 C4 C3 C2 . . . . 0.4(6) ?
C1 C2 C3 C4 . . . . -0.9(7) ?
