#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/29/2002974.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_2002974 loop_ _publ_author_name 'Ferguson, George' 'Glidewell, Christopher' 'Gregson, Richard M.' 'Lavender, Emma S.' _publ_section_title ; Crystal engineering using bisphenols: interwoven ladders, sheet and framework structures in the binary adducts of 4,4'-sulfonyldiphenol with pyrazine (2/1), 4,4'-bipyridyl (1/1), trans-1,2-bis(4-pyridyl)ethene (1/1), 1,2-bis(4-pyridyl)ethane (1/1) and 4,4'-trimethylenedipyridine (1/1), and in 4,4'-sulfonyldiphenol--4,4'-trimethylenedipiperidine--water (2/2/1) ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 573 _journal_page_last 590 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C12 H10 O4 S, C12 H12 N2' _chemical_formula_sum 'C24 H22 N2 O4 S' _chemical_formula_weight 434.50 _chemical_name_systematic ; 4,4'Sulfonyldiphenol--1,2-bis(4-pyridyl)ethane (1/1) ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 114.003(14) _cell_angle_beta 104.694(14) _cell_angle_gamma 93.690(13) _cell_formula_units_Z 2 _cell_length_a 7.7599(9) _cell_length_b 12.4866(16) _cell_length_c 12.914(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 294.0(10) _cell_measurement_theta_max 22.45 _cell_measurement_theta_min 9.84 _cell_volume 1085.6(3) _computing_cell_refinement 'SET4 & CELDIM (Enraf-Nonius, 1992)' _computing_data_collection 'CAD4 (Enraf-Nonius, 1992)' _computing_data_reduction 'DATRD2 in NRCVAX96 (Gabe et al., 1989)' _computing_molecular_graphics 'NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998)' _computing_publication_material 'NRCVAX96, SHELXL97 and WordPerfect macro PREP8 (Ferguson, 1998)' _computing_structure_refinement 'NRCVAX96 and SHELXL97 (Sheldrick, 1997b)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 294.0(10) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.000 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 4973 _diffrn_reflns_theta_full 27.42 _diffrn_reflns_theta_max 27.42 _diffrn_reflns_theta_min 2.76 _diffrn_standards_decay_% 'no decay, variation 0.7' _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_T_max .9506 _exptl_absorpt_correction_T_min .9335 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'ABSO in NRCVAX (Gabe et al., 1989)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 456 _exptl_crystal_size_max .42 _exptl_crystal_size_mid .42 _exptl_crystal_size_min .32 _refine_diff_density_max 0.434 _refine_diff_density_min -0.318 _refine_ls_extinction_coef 0.015(2) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 283 _refine_ls_number_reflns 4973 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.072 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0418 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0602P)^2^+0.2544P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1225 _reflns_number_gt 3905 _reflns_number_total 4973 _reflns_threshold_expression >2\s(I) _[local]_cod_data_source_file cf0004.cif _[local]_cod_data_source_block 6c _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Gaussian' changed to 'gaussian' 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: '_exptl_absorpt_correction_type' value 'Gaussian' changed to 'gaussian' 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 1085.7(3) _cod_database_code 2002974 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 S1 0.82235(6) 0.55444(4) 0.75430(4) 0.04529(14) Uani d . 1 . . S O11 1.01380(17) 0.56195(12) 0.80197(12) 0.0637(4) Uani d . 1 . . O O12 0.7644(2) 0.62870(11) 0.69620(12) 0.0644(4) Uani d . 1 . . O O14 0.5356(2) 0.05715(11) 0.39760(11) 0.0590(4) Uani d . 1 . . O O24 0.50738(18) 0.68579(13) 1.14705(11) 0.0567(3) Uani d . 1 . . O C11 0.7243(2) 0.40583(14) 0.65068(13) 0.0391(3) Uani d . 1 . . C C12 0.7524(2) 0.31208(15) 0.68072(14) 0.0447(4) Uani d . 1 . . C C13 0.6869(3) 0.19626(15) 0.59558(15) 0.0491(4) Uani d . 1 . . C C14 0.5920(2) 0.17269(14) 0.47903(14) 0.0429(4) Uani d . 1 . . C C15 0.5584(2) 0.26648(16) 0.45090(14) 0.0491(4) Uani d . 1 . . C C16 0.6256(3) 0.38222(15) 0.53616(14) 0.0481(4) Uani d . 1 . . C C21 0.7297(2) 0.58808(13) 0.87172(13) 0.0388(3) Uani d . 1 . . C C22 0.8382(2) 0.61042(16) 0.98433(15) 0.0480(4) Uani d . 1 . . C C23 0.7659(2) 0.64345(17) 1.07763(15) 0.0518(4) Uani d . 1 . . C C24 0.5848(2) 0.65341(14) 1.05917(14) 0.0419(4) Uani d . 1 . . C C25 0.4755(2) 0.62909(14) 0.94553(14) 0.0437(4) Uani d . 1 . . C C26 0.5482(2) 0.59739(14) 0.85305(14) 0.0429(4) Uani d . 1 . . C N31 0.3942(2) 0.01783(13) 0.16574(12) 0.0483(3) Uani d . 1 . . N C32 0.3800(3) 0.09352(16) 0.11731(16) 0.0537(4) Uani d . 1 . . C C33 0.2733(3) 0.06495(18) 0.00375(16) 0.0560(5) Uani d . 1 . . C C34 0.1713(3) -0.04915(17) -0.06678(15) 0.0523(4) Uani d . 1 . . C C35 0.1904(3) -0.12917(16) -0.01837(16) 0.0568(5) Uani d . 1 . . C C36 0.3010(3) -0.09299(16) 0.09651(16) 0.0522(4) Uani d . 1 . . C C37 0.0424(3) -0.0851(2) -0.18997(17) 0.0691(6) Uani d . 1 . . C N41 -0.2507(2) -0.26148(17) -0.63894(13) 0.0607(4) Uani d . 1 . . N C42 -0.1746(3) -0.3384(2) -0.60482(17) 0.0618(5) Uani d . 1 . . C C43 -0.0589(3) -0.30801(19) -0.49284(16) 0.0582(5) Uani d . 1 . . C C44 -0.0141(2) -0.19092(19) -0.41014(15) 0.0549(5) Uani d . 1 . . C C45 -0.0911(3) -0.1100(2) -0.44520(19) 0.0703(6) Uani d . 1 . . C C46 -0.2100(3) -0.1488(2) -0.55931(19) 0.0703(6) Uani d . 1 . . C C47 0.1154(3) -0.1543(2) -0.28671(17) 0.0700(6) Uani d . 1 . . C H14 0.4981 0.0538 0.3308 0.089 Uiso calc R 1 . . H H24 0.5830 0.6972 1.2096 0.085 Uiso calc R 1 . . H H12 0.8156 0.3277 0.7585 0.054 Uiso calc R 1 . . H H13 0.7058 0.1335 0.6157 0.059 Uiso calc R 1 . . H H15 0.4902 0.2513 0.3742 0.059 Uiso calc R 1 . . H H16 0.6043 0.4450 0.5165 0.058 Uiso calc R 1 . . H H22 0.9595 0.6032 0.9970 0.058 Uiso calc R 1 . . H H23 0.8390 0.6591 1.1533 0.062 Uiso calc R 1 . . H H25 0.3534 0.6343 0.9322 0.052 Uiso calc R 1 . . H H26 0.4753 0.5821 0.7774 0.052 Uiso calc R 1 . . H H32 0.4466 0.1708 0.1631 0.064 Uiso calc R 1 . . H H33 0.2694 0.1218 -0.0256 0.067 Uiso calc R 1 . . H H35 0.1287 -0.2078 -0.0632 0.068 Uiso calc R 1 . . H H36 0.3110 -0.1488 0.1272 0.063 Uiso calc R 1 . . H H37A -0.0695 -0.1323 -0.1991 0.083 Uiso calc R 1 . . H H37B 0.0133 -0.0137 -0.1974 0.083 Uiso calc R 1 . . H H42 -0.2012 -0.4182 -0.6601 0.074 Uiso calc R 1 . . H H43 -0.0115 -0.3664 -0.4735 0.070 Uiso calc R 1 . . H H45 -0.0634 -0.0293 -0.3924 0.084 Uiso calc R 1 . . H H46 -0.2631 -0.0929 -0.5804 0.084 Uiso calc R 1 . . H H47A 0.1451 -0.2256 -0.2790 0.084 Uiso calc R 1 . . H H47B 0.2270 -0.1070 -0.2779 0.084 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 S1 0.0500(3) 0.0392(2) 0.0382(2) 0.00062(16) 0.01294(17) 0.01030(16) O11 0.0438(7) 0.0654(8) 0.0552(8) -0.0044(6) 0.0137(6) 0.0038(6) O12 0.0994(11) 0.0450(7) 0.0531(8) 0.0071(7) 0.0283(8) 0.0236(6) O14 0.0811(10) 0.0418(6) 0.0369(6) -0.0001(6) 0.0067(6) 0.0091(5) O24 0.0539(8) 0.0759(9) 0.0389(6) 0.0187(7) 0.0144(6) 0.0227(6) C11 0.0393(8) 0.0390(8) 0.0324(7) 0.0059(6) 0.0096(6) 0.0103(6) C12 0.0498(9) 0.0473(9) 0.0306(7) 0.0039(7) 0.0054(7) 0.0157(7) C13 0.0635(11) 0.0426(9) 0.0391(8) 0.0064(8) 0.0107(8) 0.0193(7) C14 0.0445(9) 0.0415(8) 0.0342(8) 0.0035(7) 0.0099(6) 0.0105(6) C15 0.0533(10) 0.0526(9) 0.0302(7) 0.0161(8) 0.0026(7) 0.0125(7) C16 0.0588(10) 0.0440(9) 0.0372(8) 0.0189(8) 0.0088(7) 0.0159(7) C21 0.0434(8) 0.0322(7) 0.0337(7) 0.0044(6) 0.0076(6) 0.0104(6) C22 0.0405(9) 0.0599(10) 0.0420(8) 0.0153(8) 0.0069(7) 0.0233(8) C23 0.0477(10) 0.0686(12) 0.0352(8) 0.0146(8) 0.0040(7) 0.0237(8) C24 0.0451(9) 0.0412(8) 0.0367(8) 0.0087(7) 0.0097(7) 0.0160(7) C25 0.0372(8) 0.0449(9) 0.0394(8) 0.0073(7) 0.0039(6) 0.0137(7) C26 0.0434(9) 0.0404(8) 0.0314(7) 0.0031(6) -0.0002(6) 0.0103(6) N31 0.0497(8) 0.0463(8) 0.0347(7) 0.0046(6) 0.0056(6) 0.0091(6) C32 0.0593(11) 0.0422(9) 0.0441(9) -0.0019(8) 0.0073(8) 0.0108(7) C33 0.0687(12) 0.0537(10) 0.0436(9) 0.0106(9) 0.0139(8) 0.0214(8) C34 0.0524(10) 0.0563(10) 0.0341(8) 0.0165(8) 0.0091(7) 0.0080(8) C35 0.0596(11) 0.0406(9) 0.0450(9) 0.0019(8) 0.0024(8) 0.0036(7) C36 0.0599(11) 0.0423(9) 0.0450(9) 0.0086(8) 0.0100(8) 0.0138(7) C37 0.0633(13) 0.0865(15) 0.0401(10) 0.0262(11) 0.0071(9) 0.0144(10) N41 0.0490(9) 0.0903(13) 0.0355(7) 0.0141(8) 0.0103(6) 0.0222(8) C42 0.0556(11) 0.0707(13) 0.0414(10) 0.0051(10) 0.0104(8) 0.0114(9) C43 0.0549(11) 0.0718(13) 0.0449(10) 0.0135(9) 0.0130(8) 0.0239(9) C44 0.0418(9) 0.0790(13) 0.0366(8) 0.0129(9) 0.0105(7) 0.0190(9) C45 0.0744(14) 0.0667(13) 0.0475(11) 0.0143(11) 0.0075(10) 0.0102(10) C46 0.0733(14) 0.0842(16) 0.0515(11) 0.0258(12) 0.0120(10) 0.0306(11) C47 0.0533(12) 0.1002(17) 0.0385(9) 0.0218(11) 0.0068(8) 0.0165(10) 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' N N 0.0061 0.0033 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 5 1 0 -3 6 4 -1 1 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O11 S1 O12 118.23(9) no O11 S1 C11 108.62(8) no O12 S1 C11 107.03(8) no O11 S1 C21 107.41(8) no O12 S1 C21 107.97(8) no C11 S1 C21 107.10(7) no S1 C11 C12 121.06(12) no S1 C11 C16 119.12(13) no C12 C11 C16 119.74(15) no C11 C12 C13 119.97(15) no C12 C13 C14 120.09(16) no O14 C14 C13 117.83(15) no O14 C14 C15 122.58(15) no C13 C14 C15 119.58(15) no C14 C15 C16 120.05(15) no C11 C16 C15 120.47(16) no S1 C21 C22 120.42(13) no S1 C21 C26 119.75(12) no C22 C21 C26 119.78(15) no C21 C22 C23 119.83(16) no C22 C23 C24 120.42(15) no O24 C24 C23 122.90(15) no O24 C24 C25 117.50(15) no C23 C24 C25 119.60(15) no C24 C25 C26 119.87(15) no C21 C26 C25 120.49(14) no C32 N31 C36 116.34(15) no N31 C32 C33 124.09(17) no C32 C33 C34 119.55(18) no C33 C34 C35 116.54(16) no C33 C34 C37 122.54(19) no C35 C34 C37 120.91(18) no C34 C35 C36 120.09(17) no N31 C36 C35 123.32(17) no C34 C37 C47 113.61(17) no C42 N41 C46 116.77(17) no N41 C42 C43 124.2(2) no C42 C43 C44 119.3(2) no C43 C44 C45 116.85(17) no C43 C44 C47 120.6(2) no C45 C44 C47 122.6(2) no C44 C45 C46 120.1(2) no N41 C46 C45 122.7(2) no C37 C47 C44 113.62(17) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 O11 1.4373(14) no S1 O12 1.4399(14) no S1 C11 1.7591(16) no S1 C21 1.7510(17) no O14 C14 1.3528(19) no O24 C24 1.347(2) no C11 C12 1.388(2) no C11 C16 1.379(2) no C12 C13 1.374(2) no C13 C14 1.394(2) no C14 C15 1.382(2) no C15 C16 1.375(2) no C21 C22 1.386(2) no C21 C26 1.388(2) no C22 C23 1.381(2) no C23 C24 1.387(2) no C24 C25 1.392(2) no C25 C26 1.374(2) no N31 C32 1.325(2) no N31 C36 1.332(2) no C32 C33 1.373(3) no C33 C34 1.385(3) no C34 C35 1.375(3) no C34 C37 1.512(2) no C35 C36 1.378(3) no C37 C47 1.474(3) no N41 C42 1.323(3) no N41 C46 1.318(3) no C42 C43 1.376(3) no C43 C44 1.369(3) no C44 C45 1.377(3) no C44 C47 1.515(2) no C45 C46 1.389(3) 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 O14 H14 N31 . .82 1.92 2.735(2) 170 no O24 H24 N41 1_667 .82 1.89 2.706(2) 174 no C16 H16 O12 . .93 2.46 2.859(2) 106 no C22 H22 O11 . .93 2.51 2.889(2) 105 no C46 H46 O14 1_454 .93 2.57 3.476(3) 164 yes 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_publ_flag O11 S1 C11 C16 -124.45(15) no O12 S1 C11 C16 4.25(16) no C21 S1 C11 C16 119.84(14) no O11 S1 C11 C12 52.30(16) no O12 S1 C11 C12 -179.00(14) no C21 S1 C11 C12 -63.41(15) no C16 C11 C12 C13 2.0(3) no S1 C11 C12 C13 -174.69(14) no C11 C12 C13 C14 .0(3) no C12 C13 C14 O14 177.82(16) no C12 C13 C14 C15 -2.5(3) no O14 C14 C15 C16 -177.29(17) no C13 C14 C15 C16 3.1(3) no C14 C15 C16 C11 -1.1(3) no C12 C11 C16 C15 -1.5(3) no S1 C11 C16 C15 175.29(14) no O11 S1 C21 C22 -2.71(17) no O12 S1 C21 C22 -131.23(14) no C11 S1 C21 C22 113.81(14) no O11 S1 C21 C26 174.56(13) no O12 S1 C21 C26 46.04(15) no C11 S1 C21 C26 -68.92(14) no C26 C21 C22 C23 -.9(3) no S1 C21 C22 C23 176.34(14) no C21 C22 C23 C24 .6(3) no C22 C23 C24 O24 -179.70(17) no C22 C23 C24 C25 .4(3) no O24 C24 C25 C26 179.04(15) no C23 C24 C25 C26 -1.1(3) no C24 C25 C26 C21 .7(2) no C22 C21 C26 C25 .3(2) no S1 C21 C26 C25 -177.01(12) no C36 N31 C32 C33 1.8(3) no N31 C32 C33 C34 .4(3) no C32 C33 C34 C35 -2.6(3) no C32 C33 C34 C37 176.35(19) no C33 C34 C35 C36 2.5(3) no C37 C34 C35 C36 -176.42(18) no C32 N31 C36 C35 -1.9(3) no C34 C35 C36 N31 -.3(3) no C35 C34 C37 C47 -79.2(3) no C33 C34 C37 C47 101.9(3) no C46 N41 C42 C43 .5(3) no N41 C42 C43 C44 -1.4(3) no C42 C43 C44 C45 .6(3) no C42 C43 C44 C47 -178.99(19) no C43 C44 C45 C46 .9(3) no C47 C44 C45 C46 -179.6(2) no C42 N41 C46 C45 1.1(3) no C44 C45 C46 N41 -1.8(4) no C34 C37 C47 C44 179.7(2) no C43 C44 C47 C37 -126.6(2) no C45 C44 C47 C37 53.9(3) no _cod_database_fobs_code 2002974 _journal_paper_doi 10.1107/S0108768199002645