#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2012456.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_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 '\f scans, and \w scans with \k 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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0520P)^2^+0.1960P] where P = (Fo^2^+2Fc^2^)/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>2\s(I) _[local]_cod_data_source_file sk1516.cif _[local]_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 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_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_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 .0413(6) .0546(7) .0281(5) .0307(5) .0193(4) .0159(4) O2 .0528(6) .0311(5) .0297(5) .0161(5) .0168(5) .0128(4) O3 .0437(6) .0261(5) .0517(6) .0065(4) .0179(5) .0011(4) C1 .0223(6) .0273(6) .0220(5) .0093(5) .0088(5) .0057(5) C2 .0236(6) .0348(7) .0297(6) .0106(5) .0079(5) .0072(5) C11 .0249(6) .0250(6) .0228(6) .0091(5) .0092(5) .0054(5) C12 .0479(8) .0579(9) .0317(7) .0386(8) .0205(6) .0225(7) C13 .0559(9) .0717(11) .0298(7) .0451(9) .0235(7) .0274(7) C14 .0304(6) .0337(7) .0241(6) .0147(5) .0130(5) .0073(5) C15 .0230(6) .0299(6) .0254(6) .0117(5) .0077(5) .0076(5) C16 .0247(6) .0327(7) .0215(5) .0112(5) .0074(5) .0082(5) C21 .0224(6) .0268(6) .0233(6) .0091(5) .0112(5) .0060(5) C22 .0297(6) .0276(7) .0236(6) .0064(5) .0097(5) .0028(5) C23 .0360(7) .0230(6) .0312(6) .0072(5) .0152(6) .0050(5) C24 .0330(7) .0292(7) .0273(6) .0135(5) .0157(5) .0106(5) C25 .0307(6) .0301(7) .0227(6) .0083(5) .0094(5) .0056(5) C26 .0267(6) .0247(6) .0247(6) .0060(5) .0091(5) .0047(5) C31 .0252(6) .0256(6) .0238(6) .0100(5) .0099(5) .0084(5) C32 .0265(6) .0297(7) .0370(7) .0097(5) .0145(6) .0063(5) C33 .0344(7) .0293(7) .0404(7) .0135(6) .0184(6) .0055(6) C34 .0353(7) .0241(6) .0321(6) .0083(5) .0125(6) .0074(5) C35 .0269(6) .0301(7) .0369(7) .0072(5) .0136(6) .0101(5) C36 .0269(6) .0309(7) .0311(6) .0117(5) .0141(5) .0099(5) N41 .0282(6) .0360(6) .0338(6) .0125(5) .0119(5) .0063(5) C42 .0362(8) .0511(9) .0348(7) .0183(7) .0146(6) .0122(6) C43 .0345(8) .0660(11) .0368(8) .0192(8) .0168(6) .0040(7) C44 .0243(7) .0355(8) .0472(8) .0079(6) .0075(6) -.0091(6) C45 .0315(7) .0302(7) .0567(9) .0099(6) .0123(7) .0110(7) C46 .0302(7) .0376(8) .0428(8) .0110(6) .0164(6) .0119(6) C47 .0320(8) .0480(10) .0690(11) .0165(7) .0107(8) -.0162(8) 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