#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:20:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180133 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/31/7103155.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_7103155
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@90k-325nm-3h-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                90.1441(6)
_cell_angle_beta                 109.9089(5)
_cell_angle_gamma                105.7044(7)
_cell_formula_units_Z            1
_cell_length_a                   8.5943(3)
_cell_length_b                   9.6258(4)
_cell_length_c                   11.3318(4)
_cell_measurement_reflns_used    942
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     843.86(5)
_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      90(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6651
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_correction_T_min  0.9917
_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    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3308
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0390
_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)+(0.0335P)²+0.3327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0956
_reflns_number_gt                2834
_reflns_number_total             3308
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b802103a.txt
_cod_data_source_block           Diol-2HSA@90k-325nm-3h-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               7103155
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 0.46577(12) 0.12709(10) 0.31270(9) 0.0177(2) Uani 1 1 d D . .
H1O H 0.5478 0.1158 0.3778 0.021 Uiso 1 1 d RD . .
C1 C 0.38642(18) 0.41700(15) 0.10796(13) 0.0186(3) Uani 1 1 d . . .
H1A H 0.4722 0.5014 0.1564 0.022 Uiso 1 1 calc R . .
C2 C 0.26724(18) 0.42895(16) -0.00720(14) 0.0216(3) Uani 1 1 d . . .
H2A H 0.2715 0.5213 -0.0376 0.026 Uiso 1 1 calc R . .
C3 C 0.14182(18) 0.30615(17) -0.07798(14) 0.0226(3) Uani 1 1 d . . .
H3A H 0.0591 0.3143 -0.1564 0.027 Uiso 1 1 calc R . .
C4 C 0.13732(18) 0.17186(16) -0.03425(14) 0.0232(3) Uani 1 1 d . . .
H4A H 0.0519 0.0877 -0.0833 0.028 Uiso 1 1 calc R . .
C5 C 0.25678(18) 0.15886(15) 0.08103(13) 0.0192(3) Uani 1 1 d . . .
H5A H 0.2534 0.0661 0.1104 0.023 Uiso 1 1 calc R . .
C6 C 0.38108(16) 0.28203(15) 0.15298(13) 0.0153(3) Uani 1 1 d . . .
C7 C 0.51569(17) 0.27236(14) 0.28033(13) 0.0153(3) Uani 1 1 d . . .
C8 C 0.69463(17) 0.30629(15) 0.26867(13) 0.0161(3) Uani 1 1 d . . .
C9 C 0.71961(19) 0.21266(16) 0.18739(15) 0.0238(3) Uani 1 1 d . . .
H9A H 0.6272 0.1306 0.1415 0.029 Uiso 1 1 calc R . .
C10 C 0.8784(2) 0.23861(17) 0.17319(17) 0.0296(4) Uani 1 1 d . . .
H10A H 0.8946 0.1741 0.1179 0.036 Uiso 1 1 calc R . .
C11 C 1.01395(19) 0.35862(18) 0.23950(16) 0.0284(4) Uani 1 1 d . . .
H11A H 1.1230 0.3761 0.2300 0.034 Uiso 1 1 calc R . .
C12 C 0.98952(19) 0.45236(18) 0.31925(14) 0.0258(3) Uani 1 1 d . . .
H12A H 1.0819 0.5348 0.3644 0.031 Uiso 1 1 calc R . .
C13 C 0.82975(18) 0.42668(16) 0.33397(13) 0.0204(3) Uani 1 1 d . . .
H13A H 0.8136 0.4918 0.3888 0.024 Uiso 1 1 calc R . .
C14 C 0.51267(17) 0.37416(15) 0.37759(13) 0.0169(3) Uani 1 1 d . . .
C15 C 0.50442(17) 0.45393(15) 0.45538(13) 0.0172(3) Uani 1 1 d . . .
O2 O 0.72689(18) 0.10605(16) 0.51749(12) 0.0295(3) Uani 0.9368(17) 1 d PD A 1
O3 O 0.8501(3) -0.0164(3) 0.6710(2) 0.0214(4) Uani 0.9368(17) 1 d PD A 1
H3O H 0.7439 -0.0489 0.6658 0.026 Uiso 0.9368(17) 1 d PRD A 1
C21 C 0.8564(3) 0.0785(3) 0.5857(2) 0.0184(4) Uani 0.9368(17) 1 d PD A 1
C22 C 1.0301(2) 0.15010(16) 0.58365(15) 0.0207(3) Uani 0.9368(17) 1 d PD A 1
H22A H 1.0398 0.2092 0.5180 0.025 Uiso 0.9368(17) 1 calc PR A 1
C23 C 1.1746(2) 0.13562(16) 0.67007(15) 0.0202(3) Uani 0.9368(17) 1 d PD A 1
H23A H 1.1621 0.0758 0.7347 0.024 Uiso 0.9368(17) 1 calc PR A 1
C24 C 1.3479(2) 0.20319(17) 0.67339(17) 0.0231(4) Uani 0.9368(17) 1 d PD A 1
H24A H 1.3629 0.2565 0.6056 0.028 Uiso 0.9368(17) 1 calc PR A 1
C25 C 1.4868(2) 0.19416(18) 0.76666(19) 0.0249(4) Uani 0.9368(17) 1 d PD A 1
H25A H 1.4687 0.1422 0.8343 0.030 Uiso 0.9368(17) 1 calc PR A 1
C26 C 1.6681(2) 0.25787(18) 0.77523(19) 0.0311(4) Uani 0.9368(17) 1 d PD A 1
H26A H 1.7231 0.1804 0.7786 0.047 Uiso 0.9368(17) 1 calc PR A 1
H26B H 1.7311 0.3260 0.8517 0.047 Uiso 0.9368(17) 1 calc PR A 1
H26C H 1.6701 0.3094 0.7010 0.047 Uiso 0.9368(17) 1 calc PR A 1
O2B O 0.692(3) 0.135(3) 0.542(2) 0.0295(3) Uani 0.0632(17) 1 d PD A 2
O3B O 0.865(6) 0.002(5) 0.654(5) 0.0214(4) Uani 0.0632(17) 1 d PD A 2
H3OB H 0.7405 -0.0638 0.6461 0.026 Uiso 0.0632(17) 1 d PRD A 2
C21B C 0.817(5) 0.093(5) 0.570(4) 0.0184(4) Uani 0.0632(17) 1 d PD A 2
C22B C 0.950(3) 0.079(3) 0.521(2) 0.0207(3) Uani 0.0632(17) 1 d PD . 2
H22B H 0.9885 0.1732 0.4881 0.025 Uiso 0.0632(17) 1 calc PR A 2
C23B C 1.101(2) 0.041(2) 0.587(2) 0.0202(3) Uani 0.0632(17) 1 d PD . 2
H23B H 1.0914 -0.0039 0.6652 0.024 Uiso 0.0632(17) 1 calc PR A 2
C24B C 1.272(2) 0.138(2) 0.614(2) 0.0231(4) Uani 0.0632(17) 1 d PD A 2
H24B H 1.2837 0.2041 0.5535 0.028 Uiso 0.0632(17) 1 calc PR A 2
C25B C 1.410(3) 0.147(3) 0.709(2) 0.0249(4) Uani 0.0632(17) 1 d PD A 2
H25B H 1.4731 0.0981 0.6784 0.030 Uiso 0.0632(17) 1 calc PR A 2
C26B C 1.514(3) 0.195(3) 0.836(2) 0.0311(4) Uani 0.0632(17) 1 d PD A 2
H26D H 1.5462 0.1136 0.8790 0.047 Uiso 0.0632(17) 1 calc PR A 2
H26E H 1.4489 0.2341 0.8774 0.047 Uiso 0.0632(17) 1 calc PR A 2
H26F H 1.6183 0.2713 0.8403 0.047 Uiso 0.0632(17) 1 calc PR 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'
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 108.7 . . ?
C2 C1 C6 120.33(13) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C3 C2 C1 119.95(13) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C4 C3 C2 119.87(13) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 120.54(14) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C6 C5 C4 119.69(13) . . ?
C6 C5 H5A 120.2 . . ?
C4 C5 H5A 120.2 . . ?
C5 C6 C1 119.60(13) . . ?
C5 C6 C7 121.34(12) . . ?
C1 C6 C7 119.04(12) . . ?
O1 C7 C14 108.72(11) . . ?
O1 C7 C6 107.50(10) . . ?
C14 C7 C6 108.89(11) . . ?
O1 C7 C8 110.11(10) . . ?
C14 C7 C8 111.91(11) . . ?
C6 C7 C8 109.60(11) . . ?
C13 C8 C9 119.33(13) . . ?
C13 C8 C7 122.60(12) . . ?
C9 C8 C7 118.06(12) . . ?
C10 C9 C8 120.35(14) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C9 C10 C11 120.21(15) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C12 C11 C10 119.69(14) . . ?
C12 C11 H11A 120.2 . . ?
C10 C11 H11A 120.2 . . ?
C11 C12 C13 120.33(14) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C8 C13 C12 120.08(14) . . ?
C8 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C15 C14 C7 177.76(14) . . ?
C14 C15 C15 179.7(2) . 2_666 ?
C21 O3 H3O 107.6 . . ?
C21 O3 H3OB 102.9 . . ?
O2 C21 O3 121.6(2) . . ?
O2 C21 C22 122.88(17) . . ?
O3 C21 C22 115.52(17) . . ?
C23 C22 C21 122.88(14) . . ?
C23 C22 H22A 118.6 . . ?
C21 C22 H22A 118.6 . . ?
C22 C23 C24 125.49(15) . . ?
C22 C23 H23A 117.3 . . ?
C24 C23 H23A 117.3 . . ?
C25 C24 C23 122.80(16) . . ?
C25 C24 H24A 118.6 . . ?
C23 C24 H24A 118.6 . . ?
C24 C25 C26 125.83(17) . . ?
C24 C25 H25A 117.1 . . ?
C26 C25 H25A 117.1 . . ?
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 . . ?
C21B O3B H3O 100.2 . . ?
C21B O3B H3OB 98.4 . . ?
O2B C21B O3B 129(4) . . ?
O2B C21B C22B 141(4) . . ?
O3B C21B C22B 88(2) . . ?
C23B C22B C21B 127(2) . . ?
C23B C22B C23B 91.3(17) . 2_756 ?
C21B C22B C23B 118(3) . 2_756 ?
C23B C22B H22B 106.1 . . ?
C21B C22B H22B 106.1 . . ?
C23B C22B H22B 106.1 2_756 . ?
C22B C23B C24B 122.8(19) . . ?
C22B C23B C22B 88.7(17) . 2_756 ?
C24B C23B C22B 112.7(19) . 2_756 ?
C22B C23B H23B 110.2 . . ?
C24B C23B H23B 110.2 . . ?
C22B C23B H23B 110.2 2_756 . ?
C25B C24B C23B 129(2) . . ?
C25B C24B H24B 115.6 . . ?
C23B C24B H24B 115.6 . . ?
C24B C25B C26B 150(3) . . ?
C24B C25B H25B 104.9 . . ?
C26B C25B H25B 104.9 . . ?
C25B C26B H26D 109.5 . . ?
C25B C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
C25B C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 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 1.4349(16) . ?
O1 H1O 0.8606 . ?
C1 C2 1.385(2) . ?
C1 C6 1.3919(19) . ?
C1 H1A 0.9500 . ?
C2 C3 1.385(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.381(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3885(19) . ?
C5 H5A 0.9500 . ?
C6 C7 1.5334(18) . ?
C7 C14 1.4845(19) . ?
C7 C8 1.5348(18) . ?
C8 C13 1.386(2) . ?
C8 C9 1.394(2) . ?
C9 C10 1.384(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.388(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.379(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.395(2) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 C15 1.200(2) . ?
C15 C15 1.378(3) 2_666 ?
O2 C21 1.218(2) . ?
O3 C21 1.336(2) . ?
O3 H3O 0.8615 . ?
C21 C22 1.474(3) . ?
C22 C23 1.337(2) . ?
C22 H22A 0.9500 . ?
C23 C24 1.442(2) . ?
C23 H23A 0.9500 . ?
C24 C25 1.321(3) . ?
C24 H24A 0.9500 . ?
C25 C26 1.481(2) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O2B C21B 1.199(19) . ?
O3B C21B 1.33(2) . ?
O3B H3OB 1.0608 . ?
C21B C22B 1.461(19) . ?
C22B C23B 1.406(18) . ?
C22B C23B 1.55(3) 2_756 ?
C22B H22B 1.0000 . ?
C23B C24B 1.441(18) . ?
C23B C22B 1.55(3) 2_756 ?
C23B H23B 1.0000 . ?
C24B C25B 1.282(19) . ?
C24B H24B 0.9500 . ?
C25B C26B 1.409(19) . ?
C25B H25B 0.9500 . ?
C26B H26D 0.9800 . ?
C26B H26E 0.9800 . ?
C26B H26F 0.9800 . ?
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 0.1(2) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 C1 -1.0(2) . . . . ?
C4 C5 C6 C7 -179.72(12) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C2 C1 C6 C7 179.54(12) . . . . ?
C5 C6 C7 O1 -9.77(16) . . . . ?
C1 C6 C7 O1 171.50(11) . . . . ?
C5 C6 C7 C14 -127.39(13) . . . . ?
C1 C6 C7 C14 53.88(15) . . . . ?
C5 C6 C7 C8 109.89(14) . . . . ?
C1 C6 C7 C8 -68.83(15) . . . . ?
O1 C7 C8 C13 -126.70(13) . . . . ?
C14 C7 C8 C13 -5.67(18) . . . . ?
C6 C7 C8 C13 115.24(14) . . . . ?
O1 C7 C8 C9 54.32(16) . . . . ?
C14 C7 C8 C9 175.36(12) . . . . ?
C6 C7 C8 C9 -63.73(15) . . . . ?
C13 C8 C9 C10 0.8(2) . . . . ?
C7 C8 C9 C10 179.81(13) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C9 C8 C13 C12 -0.8(2) . . . . ?
C7 C8 C13 C12 -179.73(13) . . . . ?
C11 C12 C13 C8 0.2(2) . . . . ?
O2 C21 C22 C23 170.18(19) . . . . ?
O3 C21 C22 C23 -7.7(3) . . . . ?
C21 C22 C23 C24 -179.75(17) . . . . ?
C22 C23 C24 C25 174.54(16) . . . . ?
C23 C24 C25 C26 178.64(15) . . . . ?
O2B C21B C22B C23B 170(6) . . . . ?
O3B C21B C22B C23B -25(5) . . . . ?
O2B C21B C22B C23B -74(8) . . . 2_756 ?
O3B C21B C22B C23B 91(4) . . . 2_756 ?
C21B C22B C23B C24B -116(4) . . . . ?
C23B C22B C23B C24B 116(3) 2_756 . . . ?
C21B C22B C23B C22B 128(4) . . . 2_756 ?
C23B C22B C23B C22B 0.000(2) 2_756 . . 2_756 ?
C22B C23B C24B C25B 149(3) . . . . ?
C22B C23B C24B C25B -107(3) 2_756 . . . ?
C23B C24B C25B C26B -79(6) . . . . ?
