#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:20:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180133 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/31/7103152.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_7103152
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-325-1min-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                92.263(1)
_cell_angle_beta                 110.567(1)
_cell_angle_gamma                107.697(2)
_cell_formula_units_Z            1
_cell_length_a                   8.6677(3)
_cell_length_b                   9.9558(4)
_cell_length_c                   11.1736(4)
_cell_measurement_reflns_used    682
_cell_measurement_temperature    280(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     848.39(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      280(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6842
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_correction_T_min  0.9901
_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    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3329
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0434
_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)+(0.0519P)²+0.1114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1106
_reflns_number_gt                2305
_reflns_number_total             3329
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b802103a.txt
_cod_data_source_block           Diol-2HSA@280k-325nm-1min-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               7103152
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 0.49232(15) 0.14120(12) 0.31083(11) 0.0352(3) Uani 1 1 d D . .
H1O H 0.572(2) 0.147(2) 0.3840(16) 0.059(6) Uiso 1 1 d D . .
C1 C 0.3799(2) 0.39845(19) 0.09826(17) 0.0418(4) Uani 1 1 d . . .
H1A H 0.4603 0.4858 0.1468 0.050 Uiso 1 1 calc R . .
C2 C 0.2535(3) 0.3948(2) -0.02032(17) 0.0496(5) Uani 1 1 d . . .
H2A H 0.2488 0.4795 -0.0512 0.060 Uiso 1 1 calc R . .
C3 C 0.1347(2) 0.2660(2) -0.09266(17) 0.0492(5) Uani 1 1 d . . .
H3A H 0.0485 0.2635 -0.1720 0.059 Uiso 1 1 calc R . .
C4 C 0.1434(2) 0.1419(2) -0.04780(17) 0.0483(5) Uani 1 1 d . . .
H4A H 0.0643 0.0547 -0.0975 0.058 Uiso 1 1 calc R . .
C5 C 0.2696(2) 0.1451(2) 0.07124(16) 0.0408(4) Uani 1 1 d . . .
H5A H 0.2743 0.0601 0.1012 0.049 Uiso 1 1 calc R . .
C6 C 0.38795(19) 0.27366(17) 0.14537(14) 0.0288(4) Uani 1 1 d . . .
C7 C 0.53063(19) 0.28220(17) 0.27729(14) 0.0283(4) Uani 1 1 d . . .
C8 C 0.71088(19) 0.32923(18) 0.26764(14) 0.0305(4) Uani 1 1 d . . .
C9 C 0.7408(2) 0.2408(2) 0.18543(19) 0.0474(5) Uani 1 1 d . . .
H9A H 0.6522 0.1563 0.1378 0.057 Uiso 1 1 calc R . .
C10 C 0.9013(3) 0.2777(2) 0.1740(2) 0.0616(6) Uani 1 1 d . . .
H10A H 0.9205 0.2175 0.1192 0.074 Uiso 1 1 calc R . .
C11 C 1.0328(3) 0.4027(3) 0.2430(2) 0.0589(6) Uani 1 1 d . . .
H11A H 1.1412 0.4268 0.2358 0.071 Uiso 1 1 calc R . .
C12 C 1.0033(2) 0.4915(2) 0.32239(19) 0.0534(5) Uani 1 1 d . . .
H12A H 1.0913 0.5770 0.3683 0.064 Uiso 1 1 calc R . .
C13 C 0.8429(2) 0.4548(2) 0.33474(16) 0.0413(4) Uani 1 1 d . . .
H13A H 0.8242 0.5159 0.3891 0.050 Uiso 1 1 calc R . .
C14 C 0.5215(2) 0.38048(19) 0.37590(15) 0.0332(4) Uani 1 1 d . . .
C15 C 0.5078(2) 0.45603(19) 0.45478(15) 0.0347(4) Uani 1 1 d . . .
O2 O 0.70548(16) 0.12349(14) 0.54918(12) 0.0464(3) Uani 1 1 d . . .
O3 O 0.81015(16) -0.03273(14) 0.65739(12) 0.0449(3) Uani 1 1 d D . .
H3O H 0.713(2) -0.058(2) 0.671(2) 0.077(8) Uiso 1 1 d D . .
C21 C 0.8125(2) 0.06296(19) 0.57896(15) 0.0344(4) Uani 1 1 d . . .
C22 C 0.9507(2) 0.08238(19) 0.52479(16) 0.0363(4) Uani 1 1 d . . .
H22A H 0.9887 0.1791 0.5050 0.044 Uiso 1 1 calc R . .
C23 C 1.1094(2) 0.0351(2) 0.59731(16) 0.0388(4) Uani 1 1 d . . .
H23A H 1.0933 -0.0103 0.6703 0.047 Uiso 1 1 calc R . .
C24 C 1.2884(2) 0.1432(2) 0.63976(17) 0.0449(5) Uani 1 1 d . . .
H24A H 1.3094 0.2079 0.5847 0.054 Uiso 1 1 calc R . .
C25 C 1.4179(2) 0.1541(2) 0.74801(19) 0.0502(5) Uani 1 1 d . . .
H25A H 1.3918 0.0955 0.8061 0.060 Uiso 1 1 calc R . .
C26 C 1.6029(2) 0.2498(2) 0.7889(2) 0.0709(7) Uani 1 1 d . . .
H26A H 1.6777 0.1932 0.8013 0.106 Uiso 1 1 calc R . .
H26B H 1.6359 0.3112 0.8687 0.106 Uiso 1 1 calc R . .
H26C H 1.6145 0.3067 0.7232 0.106 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 106.6(14) . . ?
C6 C1 C2 120.60(17) . . ?
C6 C1 H1A 119.7 . . ?
C2 C1 H1A 119.7 . . ?
C3 C2 C1 119.99(18) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C4 C3 C2 119.80(17) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 120.40(17) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C6 C5 C4 120.31(18) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C1 118.88(15) . . ?
C5 C6 C7 122.08(15) . . ?
C1 C6 C7 119.02(14) . . ?
O1 C7 C14 108.70(13) . . ?
O1 C7 C8 109.44(12) . . ?
C14 C7 C8 112.27(13) . . ?
O1 C7 C6 107.09(13) . . ?
C14 C7 C6 109.11(13) . . ?
C8 C7 C6 110.08(12) . . ?
C13 C8 C9 118.57(16) . . ?
C13 C8 C7 123.38(14) . . ?
C9 C8 C7 118.04(14) . . ?
C10 C9 C8 120.34(18) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C11 C10 C9 120.42(19) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C12 C11 C10 119.56(18) . . ?
C12 C11 H11A 120.2 . . ?
C10 C11 H11A 120.2 . . ?
C11 C12 C13 120.28(19) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C8 C13 C12 120.81(18) . . ?
C8 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C15 C14 C7 177.42(17) . . ?
C14 C15 C15 179.6(3) . 2_666 ?
C21 O3 H3O 111.6(16) . . ?
O2 C21 O3 122.55(15) . . ?
O2 C21 C22 123.54(17) . . ?
O3 C21 C22 113.81(15) . . ?
C21 C22 C23 118.16(14) . . ?
C21 C22 C23 111.90(13) . 2_756 ?
C23 C22 C23 90.85(12) . 2_756 ?
C21 C22 H22A 111.4 . . ?
C23 C22 H22A 111.4 . . ?
C23 C22 H22A 111.4 2_756 . ?
C24 C23 C22 118.09(16) . . ?
C24 C23 C22 117.28(14) . 2_756 ?
C22 C23 C22 89.15(12) . 2_756 ?
C24 C23 H23A 110.2 . . ?
C22 C23 H23A 110.2 . . ?
C22 C23 H23A 110.2 2_756 . ?
C25 C24 C23 125.1(2) . . ?
C25 C24 H24A 117.5 . . ?
C23 C24 H24A 117.5 . . ?
C24 C25 C26 127.1(2) . . ?
C24 C25 H25A 116.4 . . ?
C26 C25 H25A 116.4 . . ?
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 1.4377(19) . ?
O1 H1O 0.850(15) . ?
C1 C6 1.380(2) . ?
C1 C2 1.382(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.374(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.365(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.378(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.534(2) . ?
C7 C14 1.484(2) . ?
C7 C8 1.533(2) . ?
C8 C13 1.374(2) . ?
C8 C9 1.389(2) . ?
C9 C10 1.380(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.374(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.368(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.384(2) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.197(2) . ?
C15 C15 1.380(3) 2_666 ?
O2 C21 1.214(2) . ?
O3 C21 1.320(2) . ?
O3 H3O 0.868(16) . ?
C21 C22 1.489(2) . ?
C22 C23 1.552(2) . ?
C22 C23 1.583(2) 2_756 ?
C22 H22A 0.9800 . ?
C23 C24 1.489(2) . ?
C23 C22 1.583(2) 2_756 ?
C23 H23A 0.9800 . ?
C24 C25 1.303(3) . ?
C24 H24A 0.9300 . ?
C25 C26 1.486(3) . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
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(3) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 C7 -179.54(15) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
C2 C1 C6 C7 179.83(16) . . . . ?
C5 C6 C7 O1 -9.84(19) . . . . ?
C1 C6 C7 O1 171.43(14) . . . . ?
C5 C6 C7 C14 -127.32(16) . . . . ?
C1 C6 C7 C14 53.94(19) . . . . ?
C5 C6 C7 C8 109.06(17) . . . . ?
C1 C6 C7 C8 -69.68(18) . . . . ?
O1 C7 C8 C13 -126.16(16) . . . . ?
C14 C7 C8 C13 -5.4(2) . . . . ?
C6 C7 C8 C13 116.39(18) . . . . ?
O1 C7 C8 C9 54.70(19) . . . . ?
C14 C7 C8 C9 175.49(15) . . . . ?
C6 C7 C8 C9 -62.7(2) . . . . ?
C13 C8 C9 C10 1.3(3) . . . . ?
C7 C8 C9 C10 -179.50(18) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
C9 C8 C13 C12 -1.0(3) . . . . ?
C7 C8 C13 C12 179.85(16) . . . . ?
C11 C12 C13 C8 -0.1(3) . . . . ?
O2 C21 C22 C23 162.83(15) . . . . ?
O3 C21 C22 C23 -20.8(2) . . . . ?
O2 C21 C22 C23 -93.7(2) . . . 2_756 ?
O3 C21 C22 C23 82.69(17) . . . 2_756 ?
C21 C22 C23 C24 -123.70(17) . . . . ?
C23 C22 C23 C24 120.77(17) 2_756 . . . ?
C21 C22 C23 C22 115.53(17) . . . 2_756 ?
C23 C22 C23 C22 0.0 2_756 . . 2_756 ?
C22 C23 C24 C25 142.38(19) . . . . ?
C22 C23 C24 C25 -112.8(2) 2_756 . . . ?
C23 C24 C25 C26 173.37(18) . . . . ?
