#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:20:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180133 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/31/7103156.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_7103156
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-8h-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                90.1271(9)
_cell_angle_beta                 109.9222(6)
_cell_angle_gamma                105.7201(5)
_cell_formula_units_Z            1
_cell_length_a                   8.5959(4)
_cell_length_b                   9.6271(4)
_cell_length_c                   11.3333(5)
_cell_measurement_reflns_used    942
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     844.12(6)
_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  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0245
_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            6724
_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         0.230
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3310
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0387
_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          0.0908
_refine_ls_wR_factor_ref         0.0948
_reflns_number_gt                2832
_reflns_number_total             3310
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b802103a.txt
_cod_data_source_block           Diol-2HSA@90k-325nm-8h-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               7103156
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 0.46582(12) 0.12720(10) 0.31264(9) 0.0179(2) Uani 1 1 d D . .
H1O H 0.5476 0.1159 0.3777 0.022 Uiso 1 1 d RD . .
C1 C 0.38638(18) 0.41701(15) 0.10799(13) 0.0187(3) Uani 1 1 d . . .
H1A H 0.4720 0.5014 0.1565 0.022 Uiso 1 1 calc R . .
C2 C 0.26725(18) 0.42892(16) -0.00726(14) 0.0216(3) Uani 1 1 d . . .
H2A H 0.2716 0.5212 -0.0377 0.026 Uiso 1 1 calc R . .
C3 C 0.14191(18) 0.30621(17) -0.07802(14) 0.0229(3) Uani 1 1 d . . .
H3A H 0.0591 0.3144 -0.1565 0.027 Uiso 1 1 calc R . .
C4 C 0.13746(18) 0.17179(16) -0.03423(14) 0.0230(3) Uani 1 1 d . . .
H4A H 0.0520 0.0876 -0.0832 0.028 Uiso 1 1 calc R . .
C5 C 0.25704(17) 0.15893(15) 0.08085(13) 0.0191(3) Uani 1 1 d . . .
H5A H 0.2539 0.0662 0.1101 0.023 Uiso 1 1 calc R . .
C6 C 0.38117(16) 0.28204(14) 0.15301(13) 0.0154(3) Uani 1 1 d . . .
C7 C 0.51574(17) 0.27236(14) 0.28041(13) 0.0154(3) Uani 1 1 d . . .
C8 C 0.69475(17) 0.30630(14) 0.26881(13) 0.0163(3) Uani 1 1 d . . .
C9 C 0.71984(19) 0.21275(16) 0.18753(15) 0.0237(3) Uani 1 1 d . . .
H9A H 0.6274 0.1307 0.1417 0.028 Uiso 1 1 calc R . .
C10 C 0.8785(2) 0.23867(18) 0.17323(17) 0.0299(4) Uani 1 1 d . . .
H10A H 0.8948 0.1742 0.1179 0.036 Uiso 1 1 calc R . .
C11 C 1.01402(19) 0.35876(18) 0.23950(16) 0.0284(4) Uani 1 1 d . . .
H11A H 1.1231 0.3763 0.2300 0.034 Uiso 1 1 calc R . .
C12 C 0.98956(19) 0.45236(17) 0.31918(14) 0.0262(3) Uani 1 1 d . . .
H12A H 1.0820 0.5348 0.3643 0.031 Uiso 1 1 calc R . .
C13 C 0.82975(18) 0.42674(16) 0.33401(13) 0.0207(3) Uani 1 1 d . . .
H13A H 0.8136 0.4919 0.3888 0.025 Uiso 1 1 calc R . .
C14 C 0.51282(16) 0.37421(15) 0.37758(13) 0.0170(3) Uani 1 1 d . . .
C15 C 0.50440(17) 0.45390(15) 0.45545(13) 0.0175(3) Uani 1 1 d . . .
O2 O 0.72667(18) 0.10605(15) 0.51746(12) 0.0295(3) Uani 0.9356(17) 1 d PD A 1
O3 O 0.8502(3) -0.0164(3) 0.6712(2) 0.0216(4) Uani 0.9356(17) 1 d PD A 1
H3O H 0.7441 -0.0489 0.6659 0.026 Uiso 0.9356(17) 1 d PRD A 1
C21 C 0.8565(2) 0.0786(2) 0.58602(17) 0.0183(4) Uani 0.9356(17) 1 d PD A 1
C22 C 1.0302(2) 0.15012(16) 0.58376(15) 0.0212(3) Uani 0.9356(17) 1 d PD A 1
H22A H 1.0398 0.2091 0.5181 0.025 Uiso 0.9356(17) 1 calc PR A 1
C23 C 1.17442(19) 0.13558(16) 0.66998(15) 0.0200(3) Uani 0.9356(17) 1 d PD A 1
H23A H 1.1618 0.0757 0.7346 0.024 Uiso 0.9356(17) 1 calc PR A 1
C24 C 1.3479(2) 0.20308(17) 0.67348(17) 0.0234(4) Uani 0.9356(17) 1 d PD A 1
H24A H 1.3630 0.2563 0.6057 0.028 Uiso 0.9356(17) 1 calc PR A 1
C25 C 1.4869(2) 0.19407(18) 0.76699(19) 0.0253(4) Uani 0.9356(17) 1 d PD A 1
H25A H 1.4689 0.1422 0.8347 0.030 Uiso 0.9356(17) 1 calc PR A 1
C26 C 1.6681(2) 0.25793(18) 0.77528(19) 0.0314(4) Uani 0.9356(17) 1 d PD A 1
H26A H 1.7233 0.1805 0.7786 0.047 Uiso 0.9356(17) 1 calc PR A 1
H26B H 1.7312 0.3262 0.8517 0.047 Uiso 0.9356(17) 1 calc PR A 1
H26C H 1.6698 0.3093 0.7010 0.047 Uiso 0.9356(17) 1 calc PR A 1
O2B O 0.693(3) 0.136(3) 0.545(2) 0.0295(3) Uani 0.0644(17) 1 d PD A 2
O3B O 0.860(6) 0.000(6) 0.650(4) 0.0216(4) Uani 0.0644(17) 1 d PD A 2
H3OB H 0.7353 -0.0655 0.6425 0.026 Uiso 0.0644(17) 1 d PRD A 2
C21B C 0.814(5) 0.090(5) 0.564(4) 0.0183(4) Uani 0.0644(17) 1 d PD A 2
C22B C 0.952(3) 0.079(3) 0.521(2) 0.0212(3) Uani 0.0644(17) 1 d PD . 2
H22B H 0.9892 0.1731 0.4870 0.025 Uiso 0.0644(17) 1 calc PR A 2
C23B C 1.102(2) 0.043(2) 0.588(2) 0.0200(3) Uani 0.0644(17) 1 d PD . 2
H23B H 1.0916 -0.0014 0.6656 0.024 Uiso 0.0644(17) 1 calc PR A 2
C24B C 1.275(2) 0.137(2) 0.615(2) 0.0234(4) Uani 0.0644(17) 1 d PD A 2
H24B H 1.2885 0.2016 0.5542 0.028 Uiso 0.0644(17) 1 calc PR A 2
C25B C 1.414(3) 0.146(3) 0.711(2) 0.0253(4) Uani 0.0644(17) 1 d PD A 2
H25B H 1.4786 0.0959 0.6828 0.030 Uiso 0.0644(17) 1 calc PR A 2
C26B C 1.513(3) 0.199(3) 0.839(2) 0.0314(4) Uani 0.0644(17) 1 d PD A 2
H26D H 1.5477 0.1200 0.8848 0.047 Uiso 0.0644(17) 1 calc PR A 2
H26E H 1.4424 0.2360 0.8760 0.047 Uiso 0.0644(17) 1 calc PR A 2
H26F H 1.6156 0.2773 0.8436 0.047 Uiso 0.0644(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 120.34(13) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C3 C2 C1 119.97(13) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C4 C3 C2 119.85(13) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 120.49(13) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C6 C5 C4 119.80(13) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C5 C6 C1 119.53(13) . . ?
C5 C6 C7 121.39(12) . . ?
C1 C6 C7 119.07(12) . . ?
O1 C7 C14 108.81(10) . . ?
O1 C7 C6 107.47(10) . . ?
C14 C7 C6 108.89(11) . . ?
O1 C7 C8 110.08(10) . . ?
C14 C7 C8 111.87(11) . . ?
C6 C7 C8 109.60(11) . . ?
C13 C8 C9 119.31(13) . . ?
C13 C8 C7 122.58(12) . . ?
C9 C8 C7 118.10(12) . . ?
C10 C9 C8 120.44(14) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C9 C10 C11 120.13(15) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C12 C11 C10 119.71(14) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
C11 C12 C13 120.42(14) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C8 C13 C12 120.00(14) . . ?
C8 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C15 C14 C7 177.65(14) . . ?
C14 C15 C15 179.6(2) . 2_666 ?
C21 O3 H3O 107.5 . . ?
C21 O3 H3OB 101.3 . . ?
O2 C21 O3 121.6(2) . . ?
O2 C21 C22 122.87(16) . . ?
O3 C21 C22 115.53(17) . . ?
C23 C22 C21 122.85(14) . . ?
C23 C22 H22A 118.6 . . ?
C21 C22 H22A 118.6 . . ?
C22 C23 C24 125.58(15) . . ?
C22 C23 H23A 117.2 . . ?
C24 C23 H23A 117.2 . . ?
C25 C24 C23 122.85(16) . . ?
C25 C24 H24A 118.6 . . ?
C23 C24 H24A 118.6 . . ?
C24 C25 C26 125.65(17) . . ?
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 102.7 . . ?
C21B O3B H3OB 98.9 . . ?
O2B C21B O3B 125(3) . . ?
O2B C21B C22B 146(4) . . ?
O3B C21B C22B 89(2) . . ?
C23B C22B C21B 128(2) . . ?
C23B C22B C23B 92.4(17) . 2_756 ?
C21B C22B C23B 115(3) . 2_756 ?
C23B C22B H22B 106.4 . . ?
C21B C22B H22B 106.4 . . ?
C23B C22B H22B 106.4 2_756 . ?
C22B C23B C24B 124.6(19) . . ?
C22B C23B C22B 87.6(17) . 2_756 ?
C24B C23B C22B 112.8(18) . 2_756 ?
C22B C23B H23B 109.8 . . ?
C24B C23B H23B 109.8 . . ?
C22B C23B H23B 109.8 2_756 . ?
C25B C24B C23B 130(2) . . ?
C25B C24B H24B 115.1 . . ?
C23B C24B H24B 115.1 . . ?
C24B C25B C26B 147(3) . . ?
C24B C25B H25B 106.5 . . ?
C26B C25B H25B 106.5 . . ?
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 1.4334(16) . ?
O1 H1O 0.8606 . ?
C1 C2 1.386(2) . ?
C1 C6 1.3919(19) . ?
C1 H1A 0.9500 . ?
C2 C3 1.384(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.382(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.389(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3885(19) . ?
C5 H5A 0.9500 . ?
C6 C7 1.5337(18) . ?
C7 C14 1.4839(19) . ?
C7 C8 1.5354(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 1.378(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.396(2) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 C15 1.2014(19) . ?
C15 C15 1.378(3) 2_666 ?
O2 C21 1.2205(19) . ?
O3 C21 1.336(2) . ?
O3 H3O 0.8616 . ?
C21 C22 1.474(2) . ?
C22 C23 1.334(2) . ?
C22 H22A 0.9500 . ?
C23 C24 1.443(2) . ?
C23 H23A 0.9500 . ?
C24 C25 1.324(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 1.194(18) . ?
O3B C21B 1.332(19) . ?
O3B H3OB 1.0608 . ?
C21B C22B 1.455(18) . ?
C22B C23B 1.396(18) . ?
C22B C23B 1.56(3) 2_756 ?
C22B H22B 1.0000 . ?
C23B C24B 1.442(18) . ?
C23B C22B 1.56(3) 2_756 ?
C23B H23B 1.0000 . ?
C24B C25B 1.290(19) . ?
C24B H24B 0.9500 . ?
C25B C26B 1.416(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 0.2(2) . . . . ?
C1 C2 C3 C4 -0.9(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C1 -1.2(2) . . . . ?
C4 C5 C6 C7 -179.83(12) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C2 C1 C6 C7 179.51(12) . . . . ?
C5 C6 C7 O1 -9.87(16) . . . . ?
C1 C6 C7 O1 171.48(11) . . . . ?
C5 C6 C7 C14 -127.58(13) . . . . ?
C1 C6 C7 C14 53.76(15) . . . . ?
C5 C6 C7 C8 109.75(14) . . . . ?
C1 C6 C7 C8 -68.90(15) . . . . ?
O1 C7 C8 C13 -126.82(13) . . . . ?
C14 C7 C8 C13 -5.71(18) . . . . ?
C6 C7 C8 C13 115.17(14) . . . . ?
O1 C7 C8 C9 54.29(16) . . . . ?
C14 C7 C8 C9 175.41(12) . . . . ?
C6 C7 C8 C9 -63.71(15) . . . . ?
C13 C8 C9 C10 0.8(2) . . . . ?
C7 C8 C9 C10 179.76(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 -179.69(13) . . . . ?
C11 C12 C13 C8 0.3(2) . . . . ?
O2 C21 C22 C23 170.35(18) . . . . ?
O3 C21 C22 C23 -7.8(3) . . . . ?
C21 C22 C23 C24 -179.68(16) . . . . ?
C22 C23 C24 C25 174.43(16) . . . . ?
C23 C24 C25 C26 178.66(15) . . . . ?
O2B C21B C22B C23B 162(6) . . . . ?
O3B C21B C22B C23B -23(5) . . . . ?
O2B C21B C22B C23B -83(8) . . . 2_756 ?
O3B C21B C22B C23B 92(4) . . . 2_756 ?
C21B C22B C23B C24B -119(3) . . . . ?
C23B C22B C23B C24B 116(3) 2_756 . . . ?
C21B C22B C23B C22B 125(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) . . . . ?
