#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:20:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180133 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/31/7103151.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_7103151
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-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                89.882(2)
_cell_angle_beta                 110.116(1)
_cell_angle_gamma                105.694(3)
_cell_formula_units_Z            1
_cell_length_a                   8.6391(2)
_cell_length_b                   9.7902(3)
_cell_length_c                   11.4484(3)
_cell_measurement_reflns_used    682
_cell_measurement_temperature    280(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     870.88(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      280(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  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9026
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9968
_exptl_absorpt_correction_T_min  0.9904
_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    1.218
_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         0.140
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3418
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0400
_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          0.0945
_refine_ls_wR_factor_ref         0.1055
_reflns_number_gt                2560
_reflns_number_total             3418
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b802103a.txt
_cod_data_source_block           Diol-2HSA@280k-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               7103151
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 0.46605(12) 0.13356(10) 0.31786(9) 0.0354(2) Uani 1 1 d D . .
H1O H 0.551(2) 0.125(2) 0.3822(15) 0.068(6) Uiso 1 1 d D . .
C1 C 0.38730(18) 0.41705(15) 0.11264(13) 0.0384(3) Uani 1 1 d . . .
H1A H 0.4707 0.4984 0.1593 0.046 Uiso 1 1 calc R . .
C2 C 0.2691(2) 0.42820(18) -0.00192(14) 0.0478(4) Uani 1 1 d . . .
H2A H 0.2732 0.5169 -0.0320 0.057 Uiso 1 1 calc R . .
C3 C 0.14551(19) 0.30852(19) -0.07150(14) 0.0504(4) Uani 1 1 d . . .
H3A H 0.0657 0.3160 -0.1483 0.060 Uiso 1 1 calc R . .
C4 C 0.14075(19) 0.17818(18) -0.02692(14) 0.0514(4) Uani 1 1 d . . .
H4A H 0.0572 0.0972 -0.0740 0.062 Uiso 1 1 calc R . .
C5 C 0.25848(18) 0.16538(16) 0.08710(13) 0.0405(3) Uani 1 1 d . . .
H5A H 0.2546 0.0761 0.1160 0.049 Uiso 1 1 calc R . .
C6 C 0.38202(15) 0.28541(14) 0.15825(11) 0.0288(3) Uani 1 1 d . . .
C7 C 0.51621(15) 0.27598(13) 0.28495(11) 0.0284(3) Uani 1 1 d . . .
C8 C 0.69383(16) 0.30816(14) 0.27309(12) 0.0320(3) Uani 1 1 d . . .
C9 C 0.7200(2) 0.21516(17) 0.19605(17) 0.0522(4) Uani 1 1 d . . .
H9A H 0.6308 0.1350 0.1532 0.063 Uiso 1 1 calc R . .
C10 C 0.8777(3) 0.2403(2) 0.1822(2) 0.0686(5) Uani 1 1 d . . .
H10A H 0.8939 0.1770 0.1302 0.082 Uiso 1 1 calc R . .
C11 C 1.0107(2) 0.3582(2) 0.24492(19) 0.0657(5) Uani 1 1 d . . .
H11A H 1.1171 0.3745 0.2362 0.079 Uiso 1 1 calc R . .
C12 C 0.98548(19) 0.4510(2) 0.31987(17) 0.0594(5) Uani 1 1 d . . .
H12A H 1.0750 0.5314 0.3619 0.071 Uiso 1 1 calc R . .
C13 C 0.82738(17) 0.42700(17) 0.33436(14) 0.0444(4) Uani 1 1 d . . .
H13A H 0.8116 0.4915 0.3857 0.053 Uiso 1 1 calc R . .
C14 C 0.51335(16) 0.37620(15) 0.38003(12) 0.0327(3) Uani 1 1 d . . .
C15 C 0.50458(16) 0.45435(15) 0.45625(12) 0.0342(3) Uani 1 1 d . . .
O2 O 0.72656(15) 0.10184(15) 0.51641(11) 0.0695(4) Uani 1 1 d . . .
O3 O 0.85171(14) -0.01300(12) 0.66934(10) 0.0531(3) Uani 1 1 d D . .
H3O H 0.745(2) -0.053(2) 0.6618(18) 0.073(6) Uiso 1 1 d D . .
C21 C 0.85602(19) 0.07921(16) 0.58497(13) 0.0410(3) Uani 1 1 d . . .
C22 C 1.0282(2) 0.14982(16) 0.58534(14) 0.0460(4) Uani 1 1 d . . .
H22A H 1.0377 0.2078 0.5222 0.055 Uiso 1 1 calc R . .
C23 C 1.17138(19) 0.13664(15) 0.66965(14) 0.0426(4) Uani 1 1 d . . .
H23A H 1.1592 0.0784 0.7321 0.051 Uiso 1 1 calc R . .
C24 C 1.3445(2) 0.20313(16) 0.67488(17) 0.0516(4) Uani 1 1 d . . .
H24A H 1.3591 0.2564 0.6101 0.062 Uiso 1 1 calc R . .
C25 C 1.4828(2) 0.19331(18) 0.76526(19) 0.0597(5) Uani 1 1 d . . .
H25A H 1.4661 0.1420 0.8305 0.072 Uiso 1 1 calc R . .
C26 C 1.6642(2) 0.2563(2) 0.7736(2) 0.0785(6) Uani 1 1 d . . .
H26A H 1.6656 0.3050 0.7010 0.118 Uiso 1 1 calc R . .
H26B H 1.7184 0.1818 0.7781 0.118 Uiso 1 1 calc R . .
H26C H 1.7254 0.3227 0.8472 0.118 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 106.8(12) . . ?
C2 C1 C6 120.33(13) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C3 C2 C1 120.21(14) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C4 C3 C2 119.55(14) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 120.86(14) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C4 C5 C6 119.94(14) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C5 C6 C1 119.11(12) . . ?
C5 C6 C7 121.68(12) . . ?
C1 C6 C7 119.20(11) . . ?
O1 C7 C14 108.67(10) . . ?
O1 C7 C8 110.16(10) . . ?
C14 C7 C8 112.20(10) . . ?
O1 C7 C6 107.47(10) . . ?
C14 C7 C6 108.83(10) . . ?
C8 C7 C6 109.39(10) . . ?
C13 C8 C9 118.63(13) . . ?
C13 C8 C7 122.78(12) . . ?
C9 C8 C7 118.58(12) . . ?
C10 C9 C8 120.51(16) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
C11 C10 C9 120.42(17) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C12 C11 C10 119.44(15) . . ?
C12 C11 H11A 120.3 . . ?
C10 C11 H11A 120.3 . . ?
C11 C12 C13 120.68(16) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C8 C13 C12 120.32(15) . . ?
C8 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C15 C14 C7 177.45(13) . . ?
C14 C15 C15 179.42(19) . 2_666 ?
C21 O3 H3O 109.4(13) . . ?
O2 C21 O3 121.18(15) . . ?
O2 C21 C22 124.42(15) . . ?
O3 C21 C22 114.39(13) . . ?
C23 C22 C21 124.14(14) . . ?
C23 C22 H22A 117.9 . . ?
C21 C22 H22A 117.9 . . ?
C22 C23 C24 126.73(15) . . ?
C22 C23 H23A 116.6 . . ?
C24 C23 H23A 116.6 . . ?
C25 C24 C23 124.12(17) . . ?
C25 C24 H24A 117.9 . . ?
C23 C24 H24A 117.9 . . ?
C24 C25 C26 126.37(19) . . ?
C24 C25 H25A 116.8 . . ?
C26 C25 H25A 116.8 . . ?
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 1.4342(15) . ?
O1 H1O 0.866(14) . ?
C1 C2 1.383(2) . ?
C1 C6 1.3847(19) . ?
C1 H1A 0.9300 . ?
C2 C3 1.374(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.369(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.3823(19) . ?
C5 H5A 0.9300 . ?
C6 C7 1.5352(17) . ?
C7 C14 1.4779(18) . ?
C7 C8 1.5342(17) . ?
C8 C13 1.3774(19) . ?
C8 C9 1.382(2) . ?
C9 C10 1.381(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.374(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.359(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.389(2) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.1967(18) . ?
C15 C15 1.380(3) 2_666 ?
O2 C21 1.2023(18) . ?
O3 C21 1.3237(18) . ?
O3 H3O 0.873(15) . ?
C21 C22 1.459(2) . ?
C22 C23 1.320(2) . ?
C22 H22A 0.9300 . ?
C23 C24 1.441(2) . ?
C23 H23A 0.9300 . ?
C24 C25 1.311(2) . ?
C24 H24A 0.9300 . ?
C25 C26 1.489(2) . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
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 0.866(14) 1.815(15) 2.6803(15) 178.7(19) .
O3 H3O O1 0.873(15) 1.873(15) 2.7337(15) 168.0(18) 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 -0.1(2) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C4 C5 C6 C1 -1.0(2) . . . . ?
C4 C5 C6 C7 -179.50(12) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C2 C1 C6 C7 179.26(12) . . . . ?
C5 C6 C7 O1 -10.06(16) . . . . ?
C1 C6 C7 O1 171.49(11) . . . . ?
C5 C6 C7 C14 -127.56(13) . . . . ?
C1 C6 C7 C14 53.98(15) . . . . ?
C5 C6 C7 C8 109.53(13) . . . . ?
C1 C6 C7 C8 -68.92(14) . . . . ?
O1 C7 C8 C13 -128.18(13) . . . . ?
C14 C7 C8 C13 -6.98(17) . . . . ?
C6 C7 C8 C13 113.90(14) . . . . ?
O1 C7 C8 C9 52.90(16) . . . . ?
C14 C7 C8 C9 174.11(12) . . . . ?
C6 C7 C8 C9 -65.01(15) . . . . ?
C13 C8 C9 C10 0.8(2) . . . . ?
C7 C8 C9 C10 179.74(15) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C9 C8 C13 C12 -0.9(2) . . . . ?
C7 C8 C13 C12 -179.80(13) . . . . ?
C11 C12 C13 C8 0.2(2) . . . . ?
O2 C21 C22 C23 172.09(16) . . . . ?
O3 C21 C22 C23 -6.9(2) . . . . ?
C21 C22 C23 C24 179.87(15) . . . . ?
C22 C23 C24 C25 175.61(16) . . . . ?
C23 C24 C25 C26 178.18(16) . . . . ?
