#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:20:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180133 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/31/7103157.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_7103157
loop_
_publ_author_name
'Zheng, Shao-Liang'
'Pham, Oanh'
'Vande Velde, Christophe M L'
'Gembicky, Milan'
'Coppens, Philip'
_publ_section_title
;
 Competitive isomerization and dimerization in co-crystals of
 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol and sorbic acid: a new look
 at stereochemical requirements for [2+2] dimerization.
;
_journal_issue                   22
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2538
_journal_page_last               2540
_journal_paper_doi               10.1039/b802103a
_journal_year                    2008
_chemical_formula_sum            'C42 H38 O6'
_chemical_formula_weight         638.72
_chemical_melting_point          ?
_chemical_name_common            Diol-2HSA@280k-before-337nm-exposure
_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                89.852(1)
_cell_angle_beta                 110.013(2)
_cell_angle_gamma                105.768(1)
_cell_formula_units_Z            1
_cell_length_a                   8.6394(2)
_cell_length_b                   9.7970(2)
_cell_length_c                   11.4362(3)
_cell_measurement_reflns_used    689
_cell_measurement_temperature    280(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     870.90(4)
_computing_cell_refinement       'Bruker APEXII'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      280(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11527
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9968
_exptl_absorpt_correction_T_min  0.9888
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'Blessing, R. (1995) Acta Crystallogr., A51, 33-38'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3418
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0378
_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)+(0.0436P)²+0.2023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0975
_reflns_number_gt                2995
_reflns_number_total             3418
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b802103a.txt
_cod_data_source_block           Diol-2HSA@280k-before-337nm-exposure
_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 

The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7103157
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
O1 O 0.46615(10) 0.13363(8) 0.31779(8) 0.0348(2) Uani 1 1 d D . .
H1O H 0.5488(19) 0.1213(17) 0.3805(14) 0.061(5) Uiso 1 1 d D . .
C1 C 0.38729(16) 0.41705(13) 0.11267(11) 0.0383(3) Uani 1 1 d . . .
H1A H 0.4707 0.4983 0.1592 0.046 Uiso 1 1 calc R . .
C2 C 0.26915(18) 0.42842(15) -0.00177(12) 0.0475(3) Uani 1 1 d . . .
H2A H 0.2734 0.5172 -0.0317 0.057 Uiso 1 1 calc R . .
C3 C 0.14525(17) 0.30852(17) -0.07152(12) 0.0504(3) Uani 1 1 d . . .
H3A H 0.0653 0.3161 -0.1482 0.061 Uiso 1 1 calc R . .
C4 C 0.14056(18) 0.17813(16) -0.02716(12) 0.0514(3) Uani 1 1 d . . .
H4A H 0.0572 0.0972 -0.0744 0.062 Uiso 1 1 calc R . .
C5 C 0.25841(16) 0.16519(13) 0.08724(11) 0.0403(3) Uani 1 1 d . . .
H5A H 0.2544 0.0760 0.1162 0.048 Uiso 1 1 calc R . .
C6 C 0.38219(13) 0.28558(12) 0.15839(9) 0.0287(2) Uani 1 1 d . . .
C7 C 0.51614(13) 0.27587(11) 0.28489(10) 0.0284(2) Uani 1 1 d . . .
C8 C 0.69398(14) 0.30821(12) 0.27312(10) 0.0318(2) Uani 1 1 d . . .
C9 C 0.71977(19) 0.21501(15) 0.19590(15) 0.0516(3) Uani 1 1 d . . .
H9A H 0.6304 0.1351 0.1529 0.062 Uiso 1 1 calc R . .
C10 C 0.8778(2) 0.24011(19) 0.18231(19) 0.0684(5) Uani 1 1 d . . .
H10A H 0.8944 0.1767 0.1305 0.082 Uiso 1 1 calc R . .
C11 C 1.01094(19) 0.3585(2) 0.24506(17) 0.0655(5) Uani 1 1 d . . .
H11A H 1.1175 0.3747 0.2365 0.079 Uiso 1 1 calc R . .
C12 C 0.98531(17) 0.45166(19) 0.31979(15) 0.0592(4) Uani 1 1 d . . .
H12A H 1.0745 0.5324 0.3613 0.071 Uiso 1 1 calc R . .
C13 C 0.82736(15) 0.42729(15) 0.33456(12) 0.0440(3) Uani 1 1 d . . .
H13A H 0.8115 0.4915 0.3860 0.053 Uiso 1 1 calc R . .
C14 C 0.51341(13) 0.37611(12) 0.38014(10) 0.0324(2) Uani 1 1 d . . .
C15 C 0.50467(14) 0.45444(12) 0.45626(10) 0.0340(3) Uani 1 1 d . . .
O2 O 0.72660(14) 0.10187(14) 0.51652(10) 0.0698(3) Uani 1 1 d . . .
O3 O 0.85181(12) -0.01303(11) 0.66943(9) 0.0528(3) Uani 1 1 d D . .
H3O H 0.7458(19) -0.0515(18) 0.6634(16) 0.069(5) Uiso 1 1 d D . .
C21 C 0.85615(17) 0.07907(14) 0.58518(11) 0.0411(3) Uani 1 1 d . . .
C22 C 1.02821(18) 0.15000(14) 0.58514(12) 0.0458(3) Uani 1 1 d . . .
H22A H 1.0378 0.2080 0.5220 0.055 Uiso 1 1 calc R . .
C23 C 1.17137(17) 0.13653(13) 0.66971(12) 0.0425(3) Uani 1 1 d . . .
H23A H 1.1591 0.0781 0.7321 0.051 Uiso 1 1 calc R . .
C24 C 1.34435(18) 0.20335(14) 0.67471(15) 0.0516(3) Uani 1 1 d . . .
H24A H 1.3590 0.2568 0.6100 0.062 Uiso 1 1 calc R . .
C25 C 1.48286(19) 0.19328(16) 0.76545(17) 0.0590(4) Uani 1 1 d . . .
H25A H 1.4659 0.1420 0.8307 0.071 Uiso 1 1 calc R . .
C26 C 1.6640(2) 0.25606(19) 0.7736(2) 0.0783(6) Uani 1 1 d . . .
H26A H 1.6656 0.3048 0.7009 0.117 Uiso 1 1 calc R . .
H26B H 1.7179 0.1816 0.7780 0.117 Uiso 1 1 calc R . .
H26C H 1.7253 0.3223 0.8473 0.117 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1O 108.9(11) . . ?
C2 C1 C6 120.49(11) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C3 C2 C1 120.16(12) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C4 C3 C2 119.57(12) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 120.86(12) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C6 C5 C4 119.83(12) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C1 C6 C5 119.09(10) . . ?
C1 C6 C7 119.37(10) . . ?
C5 C6 C7 121.52(10) . . ?
O1 C7 C14 108.76(8) . . ?
O1 C7 C6 107.58(8) . . ?
C14 C7 C6 108.75(8) . . ?
O1 C7 C8 110.05(8) . . ?
C14 C7 C8 112.07(9) . . ?
C6 C7 C8 109.52(8) . . ?
C13 C8 C9 118.95(11) . . ?
C13 C8 C7 122.68(10) . . ?
C9 C8 C7 118.36(10) . . ?
C10 C9 C8 120.32(14) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C11 C10 C9 120.37(15) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C12 C11 C10 119.50(13) . . ?
C12 C11 H11A 120.3 . . ?
C10 C11 H11A 120.3 . . ?
C11 C12 C13 120.65(14) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C8 C13 C12 120.20(13) . . ?
C8 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C15 C14 C7 177.47(11) . . ?
C14 C15 C15 179.58(17) . 2_666 ?
C21 O3 H3O 109.3(12) . . ?
O2 C21 O3 121.28(13) . . ?
O2 C21 C22 124.20(12) . . ?
O3 C21 C22 114.51(11) . . ?
C23 C22 C21 123.84(12) . . ?
C23 C22 H22A 118.1 . . ?
C21 C22 H22A 118.1 . . ?
C22 C23 C24 126.48(13) . . ?
C22 C23 H23A 116.8 . . ?
C24 C23 H23A 116.8 . . ?
C25 C24 C23 123.92(14) . . ?
C25 C24 H24A 118.0 . . ?
C23 C24 H24A 118.0 . . ?
C24 C25 C26 126.28(17) . . ?
C24 C25 H25A 116.9 . . ?
C26 C25 H25A 116.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
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
O1 C7 1.4324(13) . ?
O1 H1O 0.857(13) . ?
C1 C2 1.3834(17) . ?
C1 C6 1.3841(16) . ?
C1 H1A 0.9300 . ?
C2 C3 1.378(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.369(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.3863(18) . ?
C4 H4A 0.9300 . ?
C5 C6 1.3859(16) . ?
C5 H5A 0.9300 . ?
C6 C7 1.5344(14) . ?
C7 C14 1.4789(15) . ?
C7 C8 1.5349(14) . ?
C8 C13 1.3791(17) . ?
C8 C9 1.3829(17) . ?
C9 C10 1.3828(19) . ?
C9 H9A 0.9300 . ?
C10 C11 1.377(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.363(2) . ?
C11 H11A 0.9300 . ?
C12 C13 1.3885(18) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.1969(16) . ?
C15 C15 1.380(2) 2_666 ?
O2 C21 1.2052(16) . ?
O3 C21 1.3212(15) . ?
O3 H3O 0.869(14) . ?
C21 C22 1.4600(18) . ?
C22 C23 1.3236(19) . ?
C22 H22A 0.9300 . ?
C23 C24 1.4405(18) . ?
C23 H23A 0.9300 . ?
C24 C25 1.316(2) . ?
C24 H24A 0.9300 . ?
C25 C26 1.487(2) . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O2 0.857(13) 1.827(14) 2.6836(13) 177.9(16) .
O3 H3O O1 0.869(14) 1.875(14) 2.7336(12) 169.5(17) 2_656
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
C6 C1 C2 C3 -0.13(19) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C2 C1 C6 C5 0.79(17) . . . . ?
C2 C1 C6 C7 179.28(10) . . . . ?
C4 C5 C6 C1 -0.93(18) . . . . ?
C4 C5 C6 C7 -179.39(11) . . . . ?
C1 C6 C7 O1 171.53(9) . . . . ?
C5 C6 C7 O1 -10.02(13) . . . . ?
C1 C6 C7 C14 53.90(13) . . . . ?
C5 C6 C7 C14 -127.65(11) . . . . ?
C1 C6 C7 C8 -68.87(12) . . . . ?
C5 C6 C7 C8 109.58(11) . . . . ?
O1 C7 C8 C13 -128.21(11) . . . . ?
C14 C7 C8 C13 -7.05(15) . . . . ?
C6 C7 C8 C13 113.72(12) . . . . ?
O1 C7 C8 C9 52.95(13) . . . . ?
C14 C7 C8 C9 174.10(11) . . . . ?
C6 C7 C8 C9 -65.12(13) . . . . ?
C13 C8 C9 C10 1.0(2) . . . . ?
C7 C8 C9 C10 179.88(13) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C10 C11 C12 C13 0.9(2) . . . . ?
C9 C8 C13 C12 -0.73(19) . . . . ?
C7 C8 C13 C12 -179.57(11) . . . . ?
C11 C12 C13 C8 -0.2(2) . . . . ?
O2 C21 C22 C23 172.10(14) . . . . ?
O3 C21 C22 C23 -6.83(19) . . . . ?
C21 C22 C23 C24 179.94(12) . . . . ?
C22 C23 C24 C25 175.60(14) . . . . ?
C23 C24 C25 C26 178.00(14) . . . . ?
