#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/24/2012456.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2012456
loop_
_publ_author_name
'Zakaria, Choudhury M'
'Ferguson, George'
'Lough, Alan J.'
'Glidewell, Christopher'
_publ_section_title
;
 Adducts of 1,1,1-tris(4-hydroxyphenyl)ethane with
 1,2-bis(4-pyridyl)ethane and 1,2-bis(4-pyridyl)ethene: continuously
 interwoven structures in three dimensions
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o1
_journal_page_last               o5
_journal_paper_doi               10.1107/S0108270101017139
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C12 H12 N2, 2C20 H18 O3'
_chemical_formula_moiety         'C12 H12 N2, 2C20 H18 O3'
_chemical_formula_sum            'C52 H48 N2 O6'
_chemical_formula_weight         796.92
_chemical_name_systematic
;
1,2-Bis(4'-pyridyl)ethane--1,1,1-tris(4-hydroxyphenyl)ethane (1/2)
;
_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
_cell_angle_alpha                100.9920(16)
_cell_angle_beta                 109.4530(14)
_cell_angle_gamma                101.6700(11)
_cell_formula_units_Z            1
_cell_length_a                   10.2076(2)
_cell_length_b                   10.6559(2)
_cell_length_c                   10.9341(2)
_cell_measurement_reflns_used    4446
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.08
_cell_volume                     1054.49(4)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'PLATON (Spek, 2001)'
_computing_publication_material  'SHELXL97 and  PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full .991
_diffrn_measured_fraction_theta_max .991
_diffrn_measurement_device_type  Kappa-CCD
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .031
_diffrn_reflns_av_sigmaI/netI    .0483
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13679
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.08
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    .082
_exptl_absorpt_correction_T_max  .9854
_exptl_absorpt_correction_T_min  .9759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO-SMN; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             422
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .18
_refine_diff_density_max         .216
_refine_diff_density_min         -.281
_refine_ls_extinction_coef       .074(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          .0564
_refine_ls_R_factor_gt           .0439
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0520P)²+0.1960P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .1136
_refine_ls_wR_factor_ref         .1226
_reflns_number_gt                3886
_reflns_number_total             4797
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1516.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1054.49(3)
_cod_database_code               2012456
_cod_database_fobs_code          2012456
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 1.07976(11) .19588(11) .54229(9) .0364(3) Uani d . 1 . . O
O2 1.24756(12) .34767(10) -.20730(9) .0363(2) Uani d . 1 . . O
O3 1.07237(12) -.50019(10) -.14460(11) .0426(3) Uani d . 1 . . O
C1 1.34508(13) .04092(12) .17400(12) .0237(3) Uani d . 1 . . C
C2 1.51061(13) .07340(14) .25400(13) .0299(3) Uani d . 1 . . C
C11 1.27299(13) .08509(12) .27198(12) .0241(3) Uani d . 1 . . C
C12 1.31224(17) .06065(16) .39778(14) .0392(4) Uani d . 1 . . C
C13 1.24684(18) .09705(18) .48618(14) .0443(4) Uani d . 1 . . C
C14 1.13922(14) .15989(13) .45060(12) .0280(3) Uani d . 1 . . C
C15 1.09683(13) .18381(13) .32569(12) .0259(3) Uani d . 1 . . C
C16 1.16273(13) .14611(13) .23781(12) .0262(3) Uani d . 1 . . C
C21 1.32052(13) .11895(12) .06746(12) .0234(3) Uani d . 1 . . C
C22 1.38429(14) .25688(13) .10620(12) .0281(3) Uani d . 1 . . C
C23 1.35965(15) .33185(13) .01504(13) .0300(3) Uani d . 1 . . C
C24 1.27008(14) .26951(13) -.11934(12) .0276(3) Uani d . 1 . . C
C25 1.20579(14) .13329(13) -.16115(12) .0284(3) Uani d . 1 . . C
C26 1.23157(13) .05955(12) -.06776(12) .0261(3) Uani d . 1 . . C
C31 1.27828(13) -.10920(12) .10285(12) .0241(3) Uani d . 1 . . C
C32 1.35497(14) -.18380(13) .05045(13) .0307(3) Uani d . 1 . . C
C33 1.28890(15) -.31416(13) -.03031(14) .0336(3) Uani d . 1 . . C
C34 1.14415(15) -.37398(13) -.06062(13) .0307(3) Uani d . 1 . . C
C35 1.06642(14) -.30349(13) -.00677(13) .0310(3) Uani d . 1 . . C
C36 1.13350(13) -.17336(13) .07377(13) .0281(3) Uani d . 1 . . C
N41 .86824(12) .30647(12) .49551(11) .0327(3) Uani d . 1 . . N
C42 .81396(16) .29772(16) .58974(15) .0395(3) Uani d . 1 . . C
C43 .71869(17) .36662(18) .61082(15) .0457(4) Uani d . 1 . . C
C44 .67745(15) .45044(15) .53263(16) .0406(4) Uani d . 1 . . C
C45 .73375(16) .45926(15) .43425(17) .0408(3) Uani d . 1 . . C
C46 .82787(15) .38664(14) .41886(15) .0360(3) Uani d . 1 . . C
C47 .57473(17) .52853(18) .55278(19) .0561(5) Uani d . 1 . . C
H1 1.0110 .2263 .5072 .055 Uiso calc R 1 . . H
H2 1.1993 .2986 -.2865 .054 Uiso calc R 1 . . H
H3 1.1316 -.5353 -.1652 .064 Uiso calc R 1 . . H
H2A 1.5291 .0120 .3097 .045 Uiso calc R 1 . . H
H2B 1.5481 .1654 .3122 .045 Uiso calc R 1 . . H
H2C 1.5592 .0634 .1906 .045 Uiso calc R 1 . . H
H12 1.3860 .0178 .4239 .047 Uiso calc R 1 . . H
H13 1.2759 .0788 .5714 .053 Uiso calc R 1 . . H
H15 1.0225 .2261 .2997 .031 Uiso calc R 1 . . H
H16 1.1316 .1625 .1518 .031 Uiso calc R 1 . . H
H22 1.4464 .3004 .1979 .034 Uiso calc R 1 . . H
H23 1.4038 .4255 .0443 .036 Uiso calc R 1 . . H
H25 1.1443 .0902 -.2531 .034 Uiso calc R 1 . . H
H26 1.1870 -.0341 -.0975 .031 Uiso calc R 1 . . H
H32 1.4546 -.1443 .0706 .037 Uiso calc R 1 . . H
H33 1.3434 -.3627 -.0650 .040 Uiso calc R 1 . . H
H35 .9676 -.3444 -.0251 .037 Uiso calc R 1 . . H
H36 1.0793 -.1262 .1104 .034 Uiso calc R 1 . . H
H42 .8421 .2414 .6452 .047 Uiso calc R 1 . . H
H43 .6818 .3564 .6786 .055 Uiso calc R 1 . . H
H45 .7077 .5151 .3776 .049 Uiso calc R 1 . . H
H46 .8654 .3940 .3510 .043 Uiso calc R 1 . . H
H47A .5706 .5311 .6424 .067 Uiso calc R 1 . . H
H47B .6133 .6215 .5526 .067 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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_site_symmetry_1
_geom_angle
_geom_angle_publ_flag
C14 O1 H1 . 109.5 no
C24 O2 H2 . 109.5 no
C34 O3 H3 . 109.5 no
C31 C1 C21 . 109.27(9) no
C31 C1 C11 . 109.93(9) no
C21 C1 C11 . 109.30(9) no
C31 C1 C2 . 110.58(10) no
C21 C1 C2 . 108.43(10) no
C11 C1 C2 . 109.29(10) no
C1 C2 H2A . 109.5 no
C1 C2 H2B . 109.5 no
H2A C2 H2B . 109.5 no
C1 C2 H2C . 109.5 no
H2A C2 H2C . 109.5 no
H2B C2 H2C . 109.5 no
C12 C11 C16 . 116.72(11) no
C12 C11 C1 . 120.93(10) no
C16 C11 C1 . 122.31(10) no
C13 C12 C11 . 121.87(12) no
C13 C12 H12 . 119.1 no
C11 C12 H12 . 119.1 no
C14 C13 C12 . 120.21(12) no
C14 C13 H13 . 119.9 no
C12 C13 H13 . 119.9 no
O1 C14 C15 . 122.87(11) no
O1 C14 C13 . 117.98(11) no
C15 C14 C13 . 119.15(11) no
C14 C15 C16 . 120.03(11) no
C14 C15 H15 . 120.0 no
C16 C15 H15 . 120.0 no
C15 C16 C11 . 122.01(11) no
C15 C16 H16 . 119.0 no
C11 C16 H16 . 119.0 no
C26 C21 C22 . 116.96(11) no
C26 C21 C1 . 122.94(11) no
C22 C21 C1 . 120.04(10) no
C23 C22 C21 . 121.98(11) no
C23 C22 H22 . 119.0 no
C21 C22 H22 . 119.0 no
C22 C23 C24 . 119.64(12) no
C22 C23 H23 . 120.2 no
C24 C23 H23 . 120.2 no
O2 C24 C25 . 122.11(11) no
O2 C24 C23 . 118.01(11) no
C25 C24 C23 . 119.88(11) no
C24 C25 C26 . 119.63(11) no
C24 C25 H25 . 120.2 no
C26 C25 H25 . 120.2 no
C21 C26 C25 . 121.90(11) no
C21 C26 H26 . 119.0 no
C25 C26 H26 . 119.0 no
C36 C31 C32 . 116.93(12) no
C36 C31 C1 . 121.58(10) no
C32 C31 C1 . 121.08(11) no
C33 C32 C31 . 121.45(12) no
C33 C32 H32 . 119.3 no
C31 C32 H32 . 119.3 no
C34 C33 C32 . 120.36(12) no
C34 C33 H33 . 119.8 no
C32 C33 H33 . 119.8 no
O3 C34 C33 . 122.59(12) no
O3 C34 C35 . 117.99(12) no
C33 C34 C35 . 119.41(12) no
C36 C35 C34 . 119.72(12) no
C36 C35 H35 . 120.1 no
C34 C35 H35 . 120.1 no
C35 C36 C31 . 122.09(11) no
C35 C36 H36 . 119.0 no
C31 C36 H36 . 119.0 no
C42 N41 C46 . 117.53(12) no
N41 C42 C43 . 123.19(14) no
N41 C42 H42 . 118.4 no
C43 C42 H42 . 118.4 no
C44 C43 C42 . 119.55(14) no
C44 C43 H43 . 120.2 no
C42 C43 H43 . 120.2 no
C43 C44 C45 . 117.24(12) no
C43 C44 C47 . 121.42(15) no
C45 C44 C47 . 121.35(16) no
C46 C45 C44 . 119.80(14) no
C46 C45 H45 . 120.1 no
C44 C45 H45 . 120.1 no
N41 C46 C45 . 122.70(13) no
N41 C46 H46 . 118.7 no
C45 C46 H46 . 118.7 no
C47 C47 C44 2_666 113.21(16) no
C47 C47 H47A 2_666 108.9 no
C44 C47 H47A . 108.9 no
C47 C47 H47B 2_666 108.9 no
C44 C47 H47B . 108.9 no
H47A C47 H47B . 107.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C14 . 1.3688(14) no
O1 H1 . .84 no
O2 C24 . 1.3810(14) no
O2 H2 . .84 no
O3 C34 . 1.3678(16) no
O3 H3 . .84 no
C1 C31 . 1.5362(17) no
C1 C21 . 1.5396(16) no
C1 C11 . 1.5439(15) no
C1 C2 . 1.5503(17) no
C2 H2A . .98 no
C2 H2B . .98 no
C2 H2C . .98 no
C11 C12 . 1.3900(17) no
C11 C16 . 1.3920(16) no
C12 C13 . 1.3864(18) no
C12 H12 . .95 no
C13 C14 . 1.3852(18) no
C13 H13 . .95 no
C14 C15 . 1.3789(17) no
C15 C16 . 1.3893(16) no
C15 H15 . .95 no
C16 H16 . .95 no
C21 C26 . 1.3884(17) no
C21 C22 . 1.3983(18) no
C22 C23 . 1.3831(17) no
C22 H22 . .95 no
C23 C24 . 1.3869(18) no
C23 H23 . .95 no
C24 C25 . 1.3814(18) no
C25 C26 . 1.3928(17) no
C25 H25 . .95 no
C26 H26 . .95 no
C31 C36 . 1.3957(17) no
C31 C32 . 1.3963(17) no
C32 C33 . 1.3860(19) no
C32 H32 . .95 no
C33 C34 . 1.3826(19) no
C33 H33 . .95 no
C34 C35 . 1.3872(18) no
C35 C36 . 1.3841(19) no
C35 H35 . .95 no
C36 H36 . .95 no
N41 C42 . 1.3316(18) no
N41 C46 . 1.3369(17) no
C42 C43 . 1.383(2) no
C42 H42 . .95 no
C43 C44 . 1.382(2) no
C43 H43 . .95 no
C44 C45 . 1.387(2) no
C44 C47 . 1.5091(19) no
C45 C46 . 1.3817(19) no
C45 H45 . .95 no
C46 H46 . .95 no
C47 C47 2_666 1.488(3) no
C47 H47A . .99 no
C47 H47B . .99 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N41 . .84 1.81 2.6145(18) 159 y
O2 H2 O1 1_554 .84 1.83 2.6671(13) 175 y
O3 H3 O2 1_545 .84 1.98 2.8039(17) 168 y
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_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C31 C1 C11 C12 . 78.67(15) no
C21 C1 C11 C12 . -161.39(13) no
C2 C1 C11 C12 . -42.87(17) y
C31 C1 C11 C16 . -98.83(13) no
C21 C1 C11 C16 . 21.11(16) no
C2 C1 C11 C16 . 139.63(12) no
C16 C11 C12 C13 . -1.0(2) no
C1 C11 C12 C13 . -178.68(14) no
C11 C12 C13 C14 . -.1(3) no
C12 C13 C14 O1 . -178.90(15) no
C12 C13 C14 C15 . .9(2) no
O1 C14 C15 C16 . 179.26(12) no
C13 C14 C15 C16 . -.6(2) no
C14 C15 C16 C11 . -.6(2) no
C12 C11 C16 C15 . 1.4(2) no
C1 C11 C16 C15 . 179.02(12) no
C31 C1 C21 C26 . 9.19(15) no
C11 C1 C21 C26 . -111.15(12) no
C2 C1 C21 C26 . 129.80(12) no
C31 C1 C21 C22 . -173.54(10) no
C11 C1 C21 C22 . 66.12(13) no
C2 C1 C21 C22 . -52.93(14) y
C26 C21 C22 C23 . .53(17) no
C1 C21 C22 C23 . -176.90(11) no
C21 C22 C23 C24 . -.48(19) no
C22 C23 C24 O2 . 179.74(11) no
C22 C23 C24 C25 . .21(19) no
O2 C24 C25 C26 . -179.53(11) no
C23 C24 C25 C26 . -.02(18) no
C22 C21 C26 C25 . -.33(17) no
C1 C21 C26 C25 . 177.02(10) no
C24 C25 C26 C21 . .09(19) no
C21 C1 C31 C36 . -88.13(13) no
C11 C1 C31 C36 . 31.82(15) no
C2 C1 C31 C36 . 152.59(11) no
C21 C1 C31 C32 . 84.24(13) no
C11 C1 C31 C32 . -155.81(11) no
C2 C1 C31 C32 . -35.04(15) y
C36 C31 C32 C33 . 2.03(19) no
C1 C31 C32 C33 . -170.68(12) no
C31 C32 C33 C34 . -.3(2) no
C32 C33 C34 O3 . 177.04(12) no
C32 C33 C34 C35 . -1.6(2) no
O3 C34 C35 C36 . -177.11(12) no
C33 C34 C35 C36 . 1.6(2) no
C34 C35 C36 C31 . .28(19) no
C32 C31 C36 C35 . -2.04(18) no
C1 C31 C36 C35 . 170.63(11) no
C46 N41 C42 C43 . .3(2) no
N41 C42 C43 C44 . -.8(2) no
C42 C43 C44 C45 . .9(2) no
C42 C43 C44 C47 . -179.48(14) no
C43 C44 C45 C46 . -.5(2) no
C47 C44 C45 C46 . 179.81(14) no
C42 N41 C46 C45 . .1(2) no
C44 C45 C46 N41 . .1(2) no
C43 C44 C47 C47 2_666 -104.0(3) y
C45 C44 C47 C47 2_666 75.7(3) no
