#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:20:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180133 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/31/7103153.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_7103153
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-before-325nm-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                90.0309(6)
_cell_angle_beta                 109.7910(9)
_cell_angle_gamma                105.4502(8)
_cell_formula_units_Z            1
_cell_length_a                   8.5870(3)
_cell_length_b                   9.6052(2)
_cell_length_c                   11.3407(1)
_cell_measurement_reflns_used    942
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     844.07(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      90(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  0.0152
_diffrn_reflns_av_sigmaI/netI    0.0134
_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            11072
_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         0.290
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3317
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.001
_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          0.0780
_refine_ls_wR_factor_ref         0.0799
_reflns_number_gt                3062
_reflns_number_total             3317
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b802103a.txt
_cod_data_source_block           Diol-2HSA@90k-before-325nm-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               7103153
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 0.46438(9) 0.12607(7) 0.31308(7) 0.01395(16) Uani 1 1 d D . .
H1O H 0.5490(18) 0.1152(16) 0.3779(13) 0.036(4) Uiso 1 1 d D . .
C1 C 0.38668(13) 0.41800(11) 0.10860(9) 0.0150(2) Uani 1 1 d . . .
H1A H 0.4725 0.5019 0.1569 0.018 Uiso 1 1 calc R . .
C2 C 0.26781(13) 0.43088(11) -0.00643(10) 0.0173(2) Uani 1 1 d . . .
H2A H 0.2724 0.5236 -0.0367 0.021 Uiso 1 1 calc R . .
C3 C 0.14220(13) 0.30867(12) -0.07736(10) 0.0180(2) Uani 1 1 d . . .
H3A H 0.0600 0.3176 -0.1557 0.022 Uiso 1 1 calc R . .
C4 C 0.13719(13) 0.17346(12) -0.03334(10) 0.0181(2) Uani 1 1 d . . .
H4A H 0.0518 0.0896 -0.0822 0.022 Uiso 1 1 calc R . .
C5 C 0.25615(13) 0.15968(11) 0.08172(9) 0.0153(2) Uani 1 1 d . . .
H5A H 0.2524 0.0667 0.1111 0.018 Uiso 1 1 calc R . .
C6 C 0.38071(12) 0.28237(11) 0.15366(9) 0.0125(2) Uani 1 1 d . . .
C7 C 0.51478(12) 0.27155(10) 0.28077(9) 0.0124(2) Uani 1 1 d . . .
C8 C 0.69348(13) 0.30441(11) 0.26871(9) 0.0136(2) Uani 1 1 d . . .
C9 C 0.71824(14) 0.21039(11) 0.18741(11) 0.0197(2) Uani 1 1 d . . .
H9A H 0.6259 0.1287 0.1418 0.024 Uiso 1 1 calc R . .
C10 C 0.87691(16) 0.23561(13) 0.17285(12) 0.0258(3) Uani 1 1 d . . .
H10A H 0.8931 0.1708 0.1176 0.031 Uiso 1 1 calc R . .
C11 C 1.01246(14) 0.35514(13) 0.23858(12) 0.0255(3) Uani 1 1 d . . .
H11A H 1.1213 0.3722 0.2286 0.031 Uiso 1 1 calc R . .
C12 C 0.98818(14) 0.44921(13) 0.31856(10) 0.0229(2) Uani 1 1 d . . .
H12A H 1.0805 0.5313 0.3634 0.027 Uiso 1 1 calc R . .
C13 C 0.82865(13) 0.42418(12) 0.33370(10) 0.0179(2) Uani 1 1 d . . .
H13A H 0.8126 0.4893 0.3887 0.021 Uiso 1 1 calc R . .
C14 C 0.51197(12) 0.37346(11) 0.37756(9) 0.0137(2) Uani 1 1 d . . .
C15 C 0.50424(12) 0.45370(11) 0.45539(9) 0.0141(2) Uani 1 1 d . . .
O2 O 0.72728(10) 0.10586(9) 0.51664(7) 0.02596(19) Uani 1 1 d . . .
O3 O 0.85312(10) -0.01475(8) 0.67098(7) 0.01926(17) Uani 1 1 d D . .
H3O H 0.7449(17) -0.0508(17) 0.6662(14) 0.040(4) Uiso 1 1 d D . .
C21 C 0.85745(13) 0.07986(11) 0.58550(9) 0.0161(2) Uani 1 1 d . . .
C22 C 1.03016(14) 0.15036(11) 0.58320(10) 0.0180(2) Uani 1 1 d . . .
H22A H 1.0400 0.2091 0.5172 0.022 Uiso 1 1 calc R . .
C23 C 1.17450(13) 0.13576(11) 0.66976(10) 0.0167(2) Uani 1 1 d . . .
H23A H 1.1621 0.0762 0.7347 0.020 Uiso 1 1 calc R . .
C24 C 1.34794(14) 0.20315(11) 0.67258(11) 0.0197(2) Uani 1 1 d . . .
H24A H 1.3627 0.2558 0.6044 0.024 Uiso 1 1 calc R . .
C25 C 1.48770(14) 0.19456(11) 0.76665(11) 0.0212(2) Uani 1 1 d . . .
H25A H 1.4702 0.1439 0.8351 0.025 Uiso 1 1 calc R . .
C26 C 1.66966(14) 0.25796(13) 0.77362(12) 0.0265(3) Uani 1 1 d . . .
H26A H 1.6706 0.3081 0.6985 0.040 Uiso 1 1 calc R . .
H26B H 1.7251 0.1802 0.7779 0.040 Uiso 1 1 calc R . .
H26C H 1.7328 0.3272 0.8490 0.040 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 107.6(10) . . ?
C2 C1 C6 120.27(9) . . ?
C2 C1 H1A 119.9 . . ?
C6 C1 H1A 119.9 . . ?
C1 C2 C3 120.13(10) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 H2A 119.9 . . ?
C4 C3 C2 119.69(9) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 120.50(10) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 C6 119.85(9) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C5 C6 C1 119.55(9) . . ?
C5 C6 C7 121.41(9) . . ?
C1 C6 C7 119.03(9) . . ?
O1 C7 C14 108.86(8) . . ?
O1 C7 C6 107.47(8) . . ?
C14 C7 C6 108.87(8) . . ?
O1 C7 C8 110.13(7) . . ?
C14 C7 C8 111.89(8) . . ?
C6 C7 C8 109.50(8) . . ?
C13 C8 C9 119.34(9) . . ?
C13 C8 C7 122.59(9) . . ?
C9 C8 C7 118.07(9) . . ?
C10 C9 C8 120.30(10) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C9 C10 C11 120.29(11) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C12 C11 C10 119.63(10) . . ?
C12 C11 H11A 120.2 . . ?
C10 C11 H11A 120.2 . . ?
C11 C12 C13 120.31(10) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C8 C13 C12 120.14(10) . . ?
C8 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C15 C14 C7 177.89(10) . . ?
C14 C15 C15 179.78(15) . 2_666 ?
C21 O3 H3O 108.5(10) . . ?
O2 C21 O3 121.81(10) . . ?
O2 C21 C22 123.44(10) . . ?
O3 C21 C22 114.74(9) . . ?
C23 C22 C21 122.97(9) . . ?
C23 C22 H22A 118.5 . . ?
C21 C22 H22A 118.5 . . ?
C22 C23 C24 125.37(10) . . ?
C22 C23 H23A 117.3 . . ?
C24 C23 H23A 117.3 . . ?
C25 C24 C23 122.79(10) . . ?
C25 C24 H24A 118.6 . . ?
C23 C24 H24A 118.6 . . ?
C24 C25 C26 125.45(11) . . ?
C24 C25 H25A 117.3 . . ?
C26 C25 H25A 117.3 . . ?
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 1.4352(11) . ?
O1 H1O 0.871(13) . ?
C1 C2 1.3874(14) . ?
C1 C6 1.3943(14) . ?
C1 H1A 0.9500 . ?
C2 C3 1.3875(15) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3868(15) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3905(14) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3910(14) . ?
C5 H5A 0.9500 . ?
C6 C7 1.5344(13) . ?
C7 C14 1.4809(13) . ?
C7 C8 1.5353(13) . ?
C8 C13 1.3865(15) . ?
C8 C9 1.3947(15) . ?
C9 C10 1.3852(15) . ?
C9 H9A 0.9500 . ?
C10 C11 1.3886(18) . ?
C10 H10A 0.9500 . ?
C11 C12 1.3821(17) . ?
C11 H11A 0.9500 . ?
C12 C13 1.3956(15) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 C15 1.2014(15) . ?
C15 C15 1.380(2) 2_666 ?
O2 C21 1.2163(13) . ?
O3 C21 1.3320(13) . ?
O3 H3O 0.884(13) . ?
C21 C22 1.4663(15) . ?
C22 C23 1.3372(15) . ?
C22 H22A 0.9500 . ?
C23 C24 1.4464(15) . ?
C23 H23A 0.9500 . ?
C24 C25 1.3308(16) . ?
C24 H24A 0.9500 . ?
C25 C26 1.4926(15) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
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 0.871(13) 1.808(13) 2.6774(10) 175.9(15) .
O3 H3O O1 0.884(13) 1.844(13) 2.7185(10) 169.8(15) 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 -0.01(15) . . . . ?
C1 C2 C3 C4 -0.68(15) . . . . ?
C2 C3 C4 C5 0.53(16) . . . . ?
C3 C4 C5 C6 0.31(15) . . . . ?
C4 C5 C6 C1 -1.00(15) . . . . ?
C4 C5 C6 C7 -179.68(9) . . . . ?
C2 C1 C6 C5 0.85(15) . . . . ?
C2 C1 C6 C7 179.56(9) . . . . ?
C5 C6 C7 O1 -9.74(12) . . . . ?
C1 C6 C7 O1 171.57(8) . . . . ?
C5 C6 C7 C14 -127.50(10) . . . . ?
C1 C6 C7 C14 53.81(11) . . . . ?
C5 C6 C7 C8 109.88(10) . . . . ?
C1 C6 C7 C8 -68.81(11) . . . . ?
O1 C7 C8 C13 -126.76(10) . . . . ?
C14 C7 C8 C13 -5.54(13) . . . . ?
C6 C7 C8 C13 115.27(10) . . . . ?
O1 C7 C8 C9 54.23(11) . . . . ?
C14 C7 C8 C9 175.45(9) . . . . ?
C6 C7 C8 C9 -63.74(11) . . . . ?
C13 C8 C9 C10 0.71(16) . . . . ?
C7 C8 C9 C10 179.76(10) . . . . ?
C8 C9 C10 C11 -0.33(17) . . . . ?
C9 C10 C11 C12 -0.14(17) . . . . ?
C10 C11 C12 C13 0.23(17) . . . . ?
C9 C8 C13 C12 -0.61(15) . . . . ?
C7 C8 C13 C12 -179.62(9) . . . . ?
C11 C12 C13 C8 0.15(16) . . . . ?
O2 C21 C22 C23 170.90(10) . . . . ?
O3 C21 C22 C23 -8.15(15) . . . . ?
C21 C22 C23 C24 -179.67(10) . . . . ?
C22 C23 C24 C25 174.32(11) . . . . ?
C23 C24 C25 C26 178.21(10) . . . . ?
