data_2002978 _journal_name_full 'Acta Crystallographica, Section B' _journal_year 1999 _journal_volume B55 _journal_page_first 591 _journal_page_last 600 _publ_section_title ; Crystal Engineering using Bis-phenols and Tris-phenols. Complexes with 1,10-Phenanthroline: Hydrogen-bonded Chains in 4 ,4'-Biphenol-1,10-Phenanthroline (1/1) and 4,4'-Sulfonyldiphenol-1,10-Phenanthroline (2/3), \p-\p Stacked Chains in 4,4'-Thiodiphenol-1,10-Phenanthroline (1/2), and Pairwise-Interwoven Nets in 1,1,1-Tris(4-hydroxyphenyl)ethane-1,10-Phenanthroline-Methanol (1/1/1). ; loop_ _publ_author_name 'Ferguson, George' 'Glidewell, Christopher' 'Lavender, Emma S.' _chemical_name_systematic ; 4,4'-Thiodiphenol--1,10-phenanthroline (1/2) ; _chemical_name_common ? _chemical_formula_moiety 'C12 H10 O2 S, 2(C12 H8 N2)' _chemical_formula_sum 'C36 H26 N4 O2 S' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_weight 578.69 _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7342(5) _cell_length_b 13.3624(14) _cell_length_c 14.9843(11) _cell_angle_alpha 110.514(6) _cell_angle_beta 95.195(6) _cell_angle_gamma 95.895(7) _cell_volume 1429.3(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.64 _cell_measurement_theta_max 18.56 _cell_measurement_temperature 294.0(10) _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max .42 _exptl_crystal_size_mid .35 _exptl_crystal_size_min .22 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method ? _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 0.155 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'ABSORB in NRCVAX (Gabe et al., 1989)' _exptl_absorpt_correction_T_min 0.9455 _exptl_absorpt_correction_T_max 0.9696 _diffrn_ambient_temperature 294.0(10) _diffrn_radiation_type 'Molybdenum K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method '\q/2\q' _diffrn_reflns_number 5184 _diffrn_reflns_av_R_equivalents 0.000 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.20 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 'no decay, variation 0.5' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 1 -7 1 -3 -5 3 -4 0 _reflns_number_total 5184 _reflns_number_gt 3431 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.1004 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_number_reflns 5184 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0561P)^2^+0.0505P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.203 _refine_diff_density_min -0.203 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.030(2) 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' 'NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998)' 'NRCVAX96, SHELXL97 and WordPerfect macro PRPCIF97 (Ferguson, 1997)' 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 0.36375(7) 0.03072(4) 0.13013(4) 0.07258(19) Uani d . 1 . . S O14 0.99514(15) 0.22322(11) 0.41741(8) 0.0663(4) Uani d . 1 . . O O24 0.08412(17) 0.30651(13) -0.06518(10) 0.0772(4) Uani d . 1 . . O C11 0.5529(2) 0.10110(13) 0.21361(12) 0.0538(4) Uani d . 1 . . C C12 0.5377(2) 0.16396(15) 0.30720(12) 0.0591(5) Uani d . 1 . . C C13 0.6831(2) 0.20743(15) 0.37570(12) 0.0575(4) Uani d . 1 . . C C14 0.8485(2) 0.18691(14) 0.35218(11) 0.0515(4) Uani d . 1 . . C C15 0.8649(2) 0.12613(15) 0.25832(12) 0.0618(5) Uani d . 1 . . C C16 0.7188(3) 0.08397(15) 0.18996(12) 0.0620(5) Uani d . 1 . . C C21 0.2941(2) 0.12155(13) 0.07634(10) 0.0483(4) Uani d . 1 . . C C22 0.1162(2) 0.12248(14) 0.06042(11) 0.0549(4) Uani d . 1 . . C C23 0.0488(2) 0.18181(15) 0.01042(12) 0.0575(5) Uani d . 1 . . C C24 0.1594(2) 0.24503(14) -0.02205(11) 0.0531(4) Uani d . 1 . . C C25 0.3385(2) 0.24510(14) -0.00630(12) 0.0551(4) Uani d . 1 . . C C26 0.4046(2) 0.18255(14) 0.04110(12) 0.0536(4) Uani d . 1 . . C N31 0.89380(18) 0.22912(11) 0.58957(10) 0.0525(4) Uani d . 1 . . N C32 0.84012(19) 0.30006(13) 0.66846(11) 0.0449(4) Uani d . 1 . . C C33 0.7962(2) 0.27033(14) 0.74569(12) 0.0521(4) Uani d . 1 . . C C34 0.8110(3) 0.16413(16) 0.73920(15) 0.0684(5) Uani d . 1 . . C C35 0.8638(3) 0.09403(16) 0.65972(16) 0.0727(6) Uani d . 1 . . C C36 0.9037(2) 0.13053(15) 0.58673(14) 0.0647(5) Uani d . 1 . . C C37 0.7403(2) 0.34799(16) 0.82617(12) 0.0598(5) Uani d . 1 . . C N41 0.87423(17) 0.43519(11) 0.59691(9) 0.0510(3) Uani d . 1 . . N C42 0.82876(19) 0.40831(13) 0.67189(10) 0.0437(4) Uani d . 1 . . C C43 0.77184(19) 0.48229(13) 0.75312(11) 0.0480(4) Uani d . 1 . . C C44 0.7622(2) 0.58675(14) 0.75393(13) 0.0578(5) Uani d . 1 . . C C45 0.8095(2) 0.61360(15) 0.67954(14) 0.0618(5) Uani d . 1 . . C C46 0.8647(2) 0.53572(15) 0.60317(13) 0.0576(4) Uani d . 1 . . C C47 0.7284(2) 0.44886(16) 0.82991(12) 0.0582(5) Uani d . 1 . . C N51 0.23204(19) 0.43628(13) -0.15447(10) 0.0608(4) Uani d . 1 . . N C52 0.2832(2) 0.41071(13) -0.24258(12) 0.0487(4) Uani d . 1 . . C C53 0.3006(2) 0.48535(14) -0.28915(13) 0.0558(4) Uani d . 1 . . C C54 0.2639(3) 0.58927(17) -0.2404(2) 0.0781(6) Uani d . 1 . . C C55 0.2102(3) 0.61362(18) -0.1529(2) 0.0868(7) Uani d . 1 . . C C56 0.1955(3) 0.53514(19) -0.11229(16) 0.0777(6) Uani d . 1 . . C C57 0.3494(2) 0.45268(18) -0.38288(15) 0.0684(5) Uani d . 1 . . C N61 0.3047(2) 0.23299(13) -0.24347(12) 0.0657(4) Uani d . 1 . . N C62 0.3178(2) 0.30195(14) -0.29116(12) 0.0504(4) Uani d . 1 . . C C63 0.3610(2) 0.27259(15) -0.38517(13) 0.0579(5) Uani d . 1 . . C C64 0.3883(3) 0.16648(19) -0.43103(17) 0.0796(6) Uani d . 1 . . C C65 0.3748(3) 0.09661(19) -0.3850(2) 0.0900(7) Uani d . 1 . . C C66 0.3342(3) 0.13232(18) -0.2912(2) 0.0868(7) Uani d . 1 . . C C67 0.3761(2) 0.35096(19) -0.42946(14) 0.0698(5) Uani d . 1 . . C H14 0.9676 0.2467 0.4717 0.099 Uiso calc R 1 . . H H24 0.1575 0.3326 -0.0901 0.116 Uiso calc R 1 . . H H12 0.4272 0.1771 0.3242 0.071 Uiso calc R 1 . . H H13 0.6703 0.2507 0.4380 0.069 Uiso calc R 1 . . H H15 0.9754 0.1135 0.2411 0.074 Uiso calc R 1 . . H H16 0.7320 0.0434 0.1270 0.074 Uiso calc R 1 . . H H22 0.0402 0.0822 0.0839 0.066 Uiso calc R 1 . . H H23 -0.0720 0.1792 -0.0015 0.069 Uiso calc R 1 . . H H25 0.4146 0.2875 -0.0278 0.066 Uiso calc R 1 . . H H26 0.5249 0.1814 0.0495 0.064 Uiso calc R 1 . . H H34 0.7846 0.1418 0.7893 0.082 Uiso calc R 1 . . H H35 0.8731 0.0234 0.6543 0.087 Uiso calc R 1 . . H H36 0.9396 0.0821 0.5325 0.078 Uiso calc R 1 . . H H37 0.7114 0.3284 0.8773 0.072 Uiso calc R 1 . . H H44 0.7234 0.6376 0.8055 0.069 Uiso calc R 1 . . H H45 0.8050 0.6829 0.6797 0.074 Uiso calc R 1 . . H H46 0.8974 0.5555 0.5527 0.069 Uiso calc R 1 . . H H47 0.6912 0.4977 0.8834 0.070 Uiso calc R 1 . . H H54 0.2764 0.6415 -0.2681 0.094 Uiso calc R 1 . . H H55 0.1834 0.6822 -0.1203 0.104 Uiso calc R 1 . . H H56 0.1579 0.5529 -0.0521 0.093 Uiso calc R 1 . . H H57 0.3631 0.5029 -0.4127 0.082 Uiso calc R 1 . . H H64 0.4158 0.1439 -0.4935 0.095 Uiso calc R 1 . . H H65 0.3924 0.0254 -0.4153 0.108 Uiso calc R 1 . . H H66 0.3272 0.0833 -0.2600 0.104 Uiso calc R 1 . . H H67 0.4049 0.3313 -0.4916 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 0.0902(4) 0.0529(3) 0.0697(3) -0.0112(2) -0.0169(3) 0.0289(2) O14 0.0625(8) 0.0841(9) 0.0474(7) 0.0028(7) 0.0056(6) 0.0203(7) O24 0.0680(8) 0.1062(11) 0.0761(9) 0.0238(8) 0.0078(7) 0.0536(8) C11 0.0704(11) 0.0466(10) 0.0471(9) 0.0026(8) 0.0007(8) 0.0236(8) C12 0.0641(11) 0.0640(12) 0.0545(11) 0.0191(9) 0.0082(9) 0.0253(9) C13 0.0704(12) 0.0613(11) 0.0405(9) 0.0175(9) 0.0081(8) 0.0156(8) C14 0.0602(10) 0.0551(10) 0.0438(9) 0.0034(8) 0.0071(8) 0.0250(8) C15 0.0639(11) 0.0757(13) 0.0461(10) 0.0062(9) 0.0163(8) 0.0215(9) C16 0.0816(13) 0.0619(12) 0.0400(9) 0.0045(10) 0.0129(9) 0.0161(8) C21 0.0597(10) 0.0439(9) 0.0334(8) -0.0011(7) 0.0026(7) 0.0078(7) C22 0.0598(11) 0.0570(11) 0.0417(9) -0.0046(8) 0.0136(8) 0.0122(8) C23 0.0460(9) 0.0733(12) 0.0471(10) 0.0057(9) 0.0086(8) 0.0146(9) C24 0.0555(10) 0.0642(11) 0.0381(8) 0.0109(8) 0.0053(7) 0.0162(8) C25 0.0521(10) 0.0656(11) 0.0522(10) 0.0029(8) 0.0101(8) 0.0279(9) C26 0.0478(9) 0.0601(11) 0.0513(10) 0.0043(8) 0.0035(7) 0.0201(8) N31 0.0577(8) 0.0472(9) 0.0487(8) 0.0141(7) 0.0004(6) 0.0125(7) C32 0.0398(8) 0.0505(10) 0.0393(8) 0.0039(7) -0.0054(6) 0.0133(7) C33 0.0485(9) 0.0584(11) 0.0474(9) 0.0002(8) -0.0060(7) 0.0219(8) C34 0.0718(12) 0.0699(13) 0.0692(13) -0.0017(10) -0.0071(10) 0.0394(11) C35 0.0819(14) 0.0515(12) 0.0836(15) 0.0099(10) -0.0077(11) 0.0278(11) C36 0.0710(12) 0.0535(12) 0.0652(12) 0.0153(9) -0.0011(9) 0.0169(9) C37 0.0597(11) 0.0762(13) 0.0429(9) -0.0017(9) 0.0025(8) 0.0249(9) N41 0.0569(8) 0.0538(9) 0.0434(8) 0.0110(7) 0.0040(6) 0.0190(6) C42 0.0389(8) 0.0513(9) 0.0369(8) 0.0054(7) -0.0031(6) 0.0133(7) C43 0.0418(9) 0.0525(10) 0.0407(9) 0.0044(7) -0.0016(7) 0.0084(7) C44 0.0550(10) 0.0500(11) 0.0567(11) 0.0099(8) 0.0042(8) 0.0054(8) C45 0.0643(11) 0.0503(11) 0.0693(12) 0.0109(9) 0.0039(9) 0.0204(10) C46 0.0636(11) 0.0593(12) 0.0544(10) 0.0104(9) 0.0037(8) 0.0268(9) C47 0.0544(10) 0.0727(13) 0.0392(9) 0.0061(9) 0.0053(7) 0.0113(8) N51 0.0583(9) 0.0650(10) 0.0517(9) 0.0088(7) 0.0004(7) 0.0141(8) C52 0.0404(9) 0.0520(10) 0.0510(10) 0.0043(7) -0.0051(7) 0.0185(8) C53 0.0443(9) 0.0531(11) 0.0714(12) 0.0042(8) -0.0051(8) 0.0283(9) C54 0.0597(12) 0.0585(13) 0.1169(19) 0.0059(10) -0.0052(12) 0.0377(13) C55 0.0708(14) 0.0538(13) 0.115(2) 0.0098(10) 0.0047(13) 0.0069(14) C56 0.0671(13) 0.0764(15) 0.0657(13) 0.0090(11) 0.0017(10) -0.0015(12) C57 0.0601(12) 0.0847(15) 0.0745(13) 0.0052(10) 0.0011(10) 0.0494(12) N61 0.0647(10) 0.0595(10) 0.0823(11) 0.0081(8) 0.0040(8) 0.0390(9) C62 0.0413(9) 0.0531(10) 0.0569(10) 0.0034(7) -0.0039(7) 0.0236(8) C63 0.0447(9) 0.0633(12) 0.0578(11) 0.0082(8) 0.0005(8) 0.0136(9) C64 0.0660(13) 0.0735(15) 0.0818(15) 0.0112(11) 0.0078(11) 0.0071(12) C65 0.0713(14) 0.0582(14) 0.120(2) 0.0146(11) 0.0092(14) 0.0075(14) C66 0.0745(14) 0.0609(14) 0.136(2) 0.0083(11) 0.0023(14) 0.0531(15) C67 0.0608(12) 0.0975(17) 0.0549(11) 0.0085(11) 0.0070(9) 0.0332(12)