#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:20:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180133 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/31/7103154.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_7103154
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-1h-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                90.1378(5)
_cell_angle_beta                 109.8917(6)
_cell_angle_gamma                105.6692(5)
_cell_formula_units_Z            1
_cell_length_a                   8.5938(3)
_cell_length_b                   9.6260(3)
_cell_length_c                   11.3346(4)
_cell_measurement_reflns_used    942
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     844.32(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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0198
_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       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8782
_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    1.256
_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         0.188
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.002
_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          0.0860
_refine_ls_wR_factor_ref         0.0895
_reflns_number_gt                2901
_reflns_number_total             3318
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b802103a.txt
_cod_data_source_block           Diol-2HSA@90k-325nm-1h-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               7103154
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 0.46560(11) 0.12705(9) 0.31274(8) 0.0171(2) Uani 1 1 d D . .
H1O H 0.5476 0.1157 0.3778 0.021 Uiso 1 1 d RD . .
C1 C 0.38640(16) 0.41705(14) 0.10805(12) 0.0180(3) Uani 1 1 d . . .
H1A H 0.4721 0.5014 0.1565 0.022 Uiso 1 1 calc R . .
C2 C 0.26732(17) 0.42913(15) -0.00711(12) 0.0208(3) Uani 1 1 d . . .
H2A H 0.2718 0.5215 -0.0375 0.025 Uiso 1 1 calc R . .
C3 C 0.14176(17) 0.30649(15) -0.07795(12) 0.0220(3) Uani 1 1 d . . .
H3A H 0.0590 0.3147 -0.1564 0.026 Uiso 1 1 calc R . .
C4 C 0.13732(17) 0.17198(15) -0.03406(12) 0.0223(3) Uani 1 1 d . . .
H4A H 0.0519 0.0878 -0.0830 0.027 Uiso 1 1 calc R . .
C5 C 0.25690(16) 0.15908(14) 0.08108(12) 0.0186(3) Uani 1 1 d . . .
H5A H 0.2537 0.0663 0.1104 0.022 Uiso 1 1 calc R . .
C6 C 0.38115(15) 0.28216(13) 0.15318(11) 0.0148(3) Uani 1 1 d . . .
C7 C 0.51564(15) 0.27232(13) 0.28040(11) 0.0150(3) Uani 1 1 d . . .
C8 C 0.69461(15) 0.30620(13) 0.26881(11) 0.0156(3) Uani 1 1 d . . .
C9 C 0.71965(18) 0.21238(15) 0.18745(13) 0.0230(3) Uani 1 1 d . . .
H9A H 0.6273 0.1303 0.1416 0.028 Uiso 1 1 calc R . .
C10 C 0.87813(19) 0.23820(16) 0.17324(15) 0.0288(3) Uani 1 1 d . . .
H10A H 0.8944 0.1736 0.1181 0.035 Uiso 1 1 calc R . .
C11 C 1.01380(18) 0.35829(17) 0.23930(14) 0.0278(3) Uani 1 1 d . . .
H11A H 1.1227 0.3758 0.2295 0.033 Uiso 1 1 calc R . .
C12 C 0.98957(17) 0.45207(16) 0.31924(13) 0.0254(3) Uani 1 1 d . . .
H12A H 1.0820 0.5344 0.3644 0.031 Uiso 1 1 calc R . .
C13 C 0.82959(16) 0.42633(15) 0.33392(12) 0.0201(3) Uani 1 1 d . . .
H13A H 0.8134 0.4914 0.3887 0.024 Uiso 1 1 calc R . .
C14 C 0.51272(15) 0.37418(14) 0.37757(12) 0.0163(3) Uani 1 1 d . . .
C15 C 0.50435(15) 0.45378(13) 0.45546(11) 0.0165(3) Uani 1 1 d . . .
O2 O 0.72683(16) 0.10597(14) 0.51741(11) 0.0289(3) Uani 0.9436(16) 1 d PD A 1
O3 O 0.8510(4) -0.0156(3) 0.67146(18) 0.0211(4) Uani 0.9436(16) 1 d PD A 1
H3O H 0.7449 -0.0482 0.6662 0.025 Uiso 0.9436(16) 1 d PRD A 1
C21 C 0.8562(3) 0.0785(2) 0.5855(2) 0.0181(4) Uani 0.9436(16) 1 d PD A 1
C22 C 1.03002(18) 0.15007(15) 0.58358(13) 0.0206(3) Uani 0.9436(16) 1 d PD A 1
H22A H 1.0398 0.2091 0.5179 0.025 Uiso 0.9436(16) 1 calc PR A 1
C23 C 1.17439(18) 0.13568(14) 0.66992(13) 0.0196(3) Uani 0.9436(16) 1 d PD A 1
H23A H 1.1618 0.0760 0.7346 0.023 Uiso 0.9436(16) 1 calc PR A 1
C24 C 1.3481(2) 0.20298(15) 0.67345(15) 0.0226(3) Uani 0.9436(16) 1 d PD A 1
H24A H 1.3632 0.2559 0.6056 0.027 Uiso 0.9436(16) 1 calc PR A 1
C25 C 1.4872(2) 0.19424(16) 0.76693(17) 0.0243(3) Uani 0.9436(16) 1 d PD A 1
H25A H 1.4693 0.1427 0.8348 0.029 Uiso 0.9436(16) 1 calc PR A 1
C26 C 1.6682(2) 0.25773(16) 0.77497(17) 0.0305(4) Uani 0.9436(16) 1 d PD A 1
H26A H 1.7232 0.1802 0.7783 0.046 Uiso 0.9436(16) 1 calc PR A 1
H26B H 1.7314 0.3260 0.8513 0.046 Uiso 0.9436(16) 1 calc PR A 1
H26C H 1.6698 0.3090 0.7006 0.046 Uiso 0.9436(16) 1 calc PR A 1
O2B O 0.695(3) 0.134(3) 0.545(2) 0.0289(3) Uani 0.0564(16) 1 d PD A 2
O3B O 0.852(8) -0.011(6) 0.647(4) 0.0211(4) Uani 0.0564(16) 1 d PD A 2
H3OB H 0.7270 -0.0764 0.6395 0.025 Uiso 0.0564(16) 1 d PRD A 2
C21B C 0.826(5) 0.098(5) 0.579(4) 0.0181(4) Uani 0.0564(16) 1 d PD A 2
C22B C 0.950(3) 0.079(3) 0.523(2) 0.0206(3) Uani 0.0564(16) 1 d PD . 2
H22B H 0.9881 0.1730 0.4888 0.025 Uiso 0.0564(16) 1 calc PR A 2
C23B C 1.101(2) 0.043(2) 0.588(2) 0.0196(3) Uani 0.0564(16) 1 d PD . 2
H23B H 1.0897 -0.0036 0.6648 0.023 Uiso 0.0564(16) 1 calc PR A 2
C24B C 1.274(2) 0.138(3) 0.618(2) 0.0226(3) Uani 0.0564(16) 1 d PD A 2
H24B H 1.2860 0.2076 0.5602 0.027 Uiso 0.0564(16) 1 calc PR A 2
C25B C 1.415(3) 0.145(3) 0.711(2) 0.0243(3) Uani 0.0564(16) 1 d PD A 2
H25B H 1.4834 0.1030 0.6803 0.029 Uiso 0.0564(16) 1 calc PR A 2
C26B C 1.508(3) 0.191(3) 0.843(2) 0.0305(4) Uani 0.0564(16) 1 d PD A 2
H26D H 1.5407 0.1091 0.8855 0.046 Uiso 0.0564(16) 1 calc PR A 2
H26E H 1.4350 0.2242 0.8793 0.046 Uiso 0.0564(16) 1 calc PR A 2
H26F H 1.6124 0.2700 0.8527 0.046 Uiso 0.0564(16) 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 120.41(12) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C3 C2 C1 120.00(12) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C4 C3 C2 119.76(12) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 120.50(12) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C6 C5 C4 119.83(12) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C5 C6 C1 119.49(11) . . ?
C5 C6 C7 121.37(11) . . ?
C1 C6 C7 119.12(11) . . ?
O1 C7 C14 108.77(9) . . ?
O1 C7 C6 107.50(10) . . ?
C14 C7 C6 108.87(10) . . ?
O1 C7 C8 110.14(9) . . ?
C14 C7 C8 111.82(10) . . ?
C6 C7 C8 109.64(10) . . ?
C13 C8 C9 119.29(12) . . ?
C13 C8 C7 122.68(11) . . ?
C9 C8 C7 118.02(11) . . ?
C10 C9 C8 120.34(13) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C9 C10 C11 120.29(13) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C12 C11 C10 119.67(12) . . ?
C12 C11 H11A 120.2 . . ?
C10 C11 H11A 120.2 . . ?
C11 C12 C13 120.22(13) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C8 C13 C12 120.18(13) . . ?
C8 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C15 C14 C7 177.65(13) . . ?
C14 C15 C15 179.47(18) . 2_666 ?
C21 O3 H3O 107.2 . . ?
C21 O3 H3OB 103.1 . . ?
O2 C21 O3 121.8(2) . . ?
O2 C21 C22 123.00(16) . . ?
O3 C21 C22 115.12(18) . . ?
C23 C22 C21 122.98(13) . . ?
C23 C22 H22A 118.5 . . ?
C21 C22 H22A 118.5 . . ?
C22 C23 C24 125.67(13) . . ?
C22 C23 H23A 117.2 . . ?
C24 C23 H23A 117.2 . . ?
C25 C24 C23 122.99(14) . . ?
C25 C24 H24A 118.5 . . ?
C23 C24 H24A 118.5 . . ?
C24 C25 C26 125.69(15) . . ?
C24 C25 H25A 117.2 . . ?
C26 C25 H25A 117.2 . . ?
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 104.5 . . ?
C21B O3B H3OB 105.7 . . ?
O2B C21B O3B 126(4) . . ?
O2B C21B C22B 137(4) . . ?
O3B C21B C22B 89(3) . . ?
C23B C22B C21B 124(2) . . ?
C23B C22B C23B 91.2(18) . 2_756 ?
C21B C22B C23B 122(3) . 2_756 ?
C23B C22B H22B 105.6 . . ?
C21B C22B H22B 105.6 . . ?
C23B C22B H22B 105.6 2_756 . ?
C22B C23B C24B 125(2) . . ?
C22B C23B C22B 88.8(18) . 2_756 ?
C24B C23B C22B 112.9(19) . 2_756 ?
C22B C23B H23B 109.4 . . ?
C24B C23B H23B 109.4 . . ?
C22B C23B H23B 109.4 2_756 . ?
C25B C24B C23B 131(2) . . ?
C25B C24B H24B 114.6 . . ?
C23B C24B H24B 114.6 . . ?
C24B C25B C26B 145(3) . . ?
C24B C25B H25B 107.7 . . ?
C26B C25B H25B 107.7 . . ?
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 1.4351(14) . ?
O1 H1O 0.8608 . ?
C1 C2 1.3858(18) . ?
C1 C6 1.3918(18) . ?
C1 H1A 0.9500 . ?
C2 C3 1.3858(19) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3838(19) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3899(18) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3892(18) . ?
C5 H5A 0.9500 . ?
C6 C7 1.5328(17) . ?
C7 C14 1.4839(17) . ?
C7 C8 1.5349(16) . ?
C8 C13 1.3843(18) . ?
C8 C9 1.3959(18) . ?
C9 C10 1.3817(19) . ?
C9 H9A 0.9500 . ?
C10 C11 1.389(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.380(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.3968(18) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 C15 1.2006(18) . ?
C15 C15 1.378(2) 2_666 ?
O2 C21 1.216(2) . ?
O3 C21 1.3357(18) . ?
O3 H3O 0.8617 . ?
C21 C22 1.474(2) . ?
C22 C23 1.335(2) . ?
C22 H22A 0.9500 . ?
C23 C24 1.445(2) . ?
C23 H23A 0.9500 . ?
C24 C25 1.323(2) . ?
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 1.202(19) . ?
O3B C21B 1.33(2) . ?
O3B H3OB 1.0611 . ?
C21B C22B 1.467(19) . ?
C22B C23B 1.396(18) . ?
C22B C23B 1.57(3) 2_756 ?
C22B H22B 1.0000 . ?
C23B C24B 1.445(18) . ?
C23B C22B 1.57(3) 2_756 ?
C23B H23B 1.0000 . ?
C24B C25B 1.293(19) . ?
C24B H24B 0.9500 . ?
C25B C26B 1.429(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 0.16(19) . . . . ?
C1 C2 C3 C4 -0.88(19) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C3 C4 C5 C6 0.45(19) . . . . ?
C4 C5 C6 C1 -1.16(18) . . . . ?
C4 C5 C6 C7 -179.76(11) . . . . ?
C2 C1 C6 C5 0.87(18) . . . . ?
C2 C1 C6 C7 179.50(11) . . . . ?
C5 C6 C7 O1 -9.89(15) . . . . ?
C1 C6 C7 O1 171.51(10) . . . . ?
C5 C6 C7 C14 -127.54(12) . . . . ?
C1 C6 C7 C14 53.85(14) . . . . ?
C5 C6 C7 C8 109.84(12) . . . . ?
C1 C6 C7 C8 -68.76(14) . . . . ?
O1 C7 C8 C13 -126.73(12) . . . . ?
C14 C7 C8 C13 -5.67(16) . . . . ?
C6 C7 C8 C13 115.18(13) . . . . ?
O1 C7 C8 C9 54.31(14) . . . . ?
C14 C7 C8 C9 175.37(11) . . . . ?
C6 C7 C8 C9 -63.78(14) . . . . ?
C13 C8 C9 C10 0.78(19) . . . . ?
C7 C8 C9 C10 179.78(12) . . . . ?
C8 C9 C10 C11 -0.4(2) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C9 C8 C13 C12 -0.76(19) . . . . ?
C7 C8 C13 C12 -179.71(11) . . . . ?
C11 C12 C13 C8 0.3(2) . . . . ?
O2 C21 C22 C23 170.11(17) . . . . ?
O3 C21 C22 C23 -7.4(3) . . . . ?
C21 C22 C23 C24 -179.88(15) . . . . ?
C22 C23 C24 C25 174.42(14) . . . . ?
C23 C24 C25 C26 178.56(14) . . . . ?
O2B C21B C22B C23B 176(5) . . . . ?
O3B C21B C22B C23B -37(5) . . . . ?
O2B C21B C22B C23B -66(7) . . . 2_756 ?
O3B C21B C22B C23B 80(4) . . . 2_756 ?
C21B C22B C23B C24B -111(4) . . . . ?
C23B C22B C23B C24B 117(3) 2_756 . . . ?
C21B C22B C23B C22B 131(4) . . . 2_756 ?
C23B C22B C23B C22B 0.000(3) 2_756 . . 2_756 ?
C22B C23B C24B C25B 151(3) . . . . ?
C22B C23B C24B C25B -104(3) 2_756 . . . ?
C23B C24B C25B C26B -76(6) . . . . ?
