#------------------------------------------------------------------------------ #$Date: 2009-11-14 15:09:05 +0200 (Sat, 14 Nov 2009) $ #$Revision: 846 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2002980.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_2002980 _journal_name_full 'Acta Crystallographica, Section B' _journal_volume 55 _journal_year 1999 _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 ; 1,1,1-Tris(4-hydroxyphenyl)ethane--1,10-phenanthroline--methanol (1/1/1) ; _chemical_name_common ? _chemical_formula_moiety 'C20 H18 O3, C12 H8 N2, C H4 O' _chemical_formula_sum 'C33 H30 N2 O4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_weight 518.59 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z' 'x, -y+1/2, z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z' '-x, y-1/2, -z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 22.811(3) _cell_length_b 22.029(3) _cell_length_c 10.7965(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5425.3(12) _cell_formula_units_Z 8 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.93 _cell_measurement_theta_max 15.70 _cell_measurement_temperature 294.0(10) _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max .42 _exptl_crystal_size_mid .42 _exptl_crystal_size_min .14 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method ? _exptl_crystal_F_000 2192 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min 1.0000 _exptl_absorpt_correction_T_max 1.0000 _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 5200 _diffrn_reflns_av_R_equivalents 0.008 _diffrn_reflns_av_sigmaI/netI 0.0785 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.15 _diffrn_reflns_theta_full 25.15 _diffrn_measured_fraction_theta_max 0.99 _diffrn_measured_fraction_theta_full 0.99 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1.6 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -6 -9 0 9 2 3 9 -2 3 _reflns_number_total 4861 _reflns_number_gt 2178 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1305 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1075 _refine_ls_goodness_of_fit_ref 0.874 _refine_ls_restrained_S_all 0.874 _refine_ls_number_reflns 4861 _refine_ls_number_parameters 358 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0580P)^2^] 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 0.158 _refine_diff_density_min -0.143 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0025(3) 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' ##'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 C1 -0.16889(7) 0.13242(8) 0.44931(19) 0.0420(5) Uani d . 1 . . C C2 -0.12824(9) 0.07829(9) 0.4818(2) 0.0595(6) Uani d . 1 . . C C11 -0.12945(7) 0.18741(8) 0.42207(19) 0.0402(5) Uani d . 1 . . C C12 -0.13105(8) 0.24074(9) 0.48848(19) 0.0471(5) Uani d . 1 . . C C13 -0.09496(9) 0.28919(9) 0.4603(2) 0.0514(5) Uani d . 1 . . C C14 -0.05624(9) 0.28508(9) 0.3644(2) 0.0526(6) Uani d . 1 . . C O14 -0.01994(9) 0.33235(8) 0.33196(16) 0.0879(6) Uani d . 1 . . O C15 -0.05346(9) 0.23247(10) 0.2961(2) 0.0583(6) Uani d . 1 . . C C16 -0.08960(9) 0.18476(9) 0.3246(2) 0.0533(6) Uani d . 1 . . C C21 -0.20458(8) 0.11707(8) 0.33243(19) 0.0420(5) Uani d . 1 . . C C22 -0.22405(9) 0.05840(9) 0.3074(2) 0.0521(6) Uani d . 1 . . C C23 -0.25645(9) 0.04520(10) 0.2026(2) 0.0574(6) Uani d . 1 . . C C24 -0.27059(8) 0.09013(10) 0.1193(2) 0.0506(6) Uani d . 1 . . C O24 -0.30283(7) 0.07455(7) 0.01706(14) 0.0709(5) Uani d . 1 . . O C25 -0.25273(8) 0.14858(9) 0.14228(19) 0.0513(5) Uani d . 1 . . C C26 -0.22046(9) 0.16144(9) 0.2477(2) 0.0491(5) Uani d . 1 . . C C31 -0.21001(8) 0.14540(8) 0.55852(19) 0.0425(5) Uani d . 1 . . C C32 -0.26691(8) 0.16467(10) 0.5431(2) 0.0558(6) Uani d . 1 . . C C33 -0.30353(9) 0.17657(10) 0.6424(2) 0.0591(6) Uani d . 1 . . C C34 -0.28382(9) 0.16879(9) 0.7608(2) 0.0510(6) Uani d . 1 . . C O34 -0.31872(6) 0.17712(8) 0.86381(14) 0.0723(5) Uani d . 1 . . O C35 -0.22688(9) 0.15172(11) 0.7795(2) 0.0665(7) Uani d . 1 . . C C36 -0.19098(9) 0.14054(10) 0.6794(2) 0.0630(7) Uani d . 1 . . C N41 0.02443(9) 0.37652(10) 0.56006(19) 0.0681(6) Uani d . 1 . . N C42 0.07088(13) 0.34605(14) 0.5959(3) 0.0935(9) Uani d . 1 . . C C43 0.10249(14) 0.3596(2) 0.7021(4) 0.1140(13) Uani d . 1 . . C C44 0.08533(15) 0.4065(2) 0.7739(3) 0.1087(12) Uani d . 1 . . C C45 0.03554(13) 0.44034(14) 0.7404(3) 0.0792(8) Uani d . 1 . . C C46 0.01375(17) 0.49021(17) 0.8110(3) 0.1045(12) Uani d . 1 . . C C47 -0.03415(19) 0.51962(15) 0.7756(4) 0.1081(12) Uani d . 1 . . C C48 -0.06523(14) 0.50418(12) 0.6651(3) 0.0791(8) Uani d . 1 . . C C49 -0.11577(18) 0.53446(14) 0.6256(4) 0.1081(12) Uani d . 1 . . C C410 -0.14212(15) 0.51726(19) 0.5199(5) 0.1152(14) Uani d . 1 . . C C411 -0.11815(14) 0.47019(15) 0.4536(3) 0.0954(10) Uani d . 1 . . C N412 -0.07091(9) 0.43950(9) 0.4859(2) 0.0711(6) Uani d . 1 . . N C413 -0.04475(10) 0.45656(10) 0.5925(2) 0.0591(6) Uani d . 1 . . C C414 0.00641(10) 0.42342(11) 0.6310(2) 0.0590(6) Uani d . 1 . . C O51 0.06663(7) 0.31812(10) 0.16278(16) 0.0862(6) Uani d . 1 . . O C51 0.03656(12) 0.32226(14) 0.0494(3) 0.0935(9) Uani d . 1 . . C H2A -0.1015 0.0902 0.5460 0.089 Uiso calc R 1 . . H H2B -0.1066 0.0664 0.4096 0.089 Uiso calc R 1 . . H H2C -0.1515 0.0447 0.5101 0.089 Uiso calc R 1 . . H H12 -0.1572 0.2443 0.5542 0.057 Uiso calc R 1 . . H H13 -0.0971 0.3246 0.5069 0.062 Uiso calc R 1 . . H H14 -0.0159 0.3552 0.3913 0.132 Uiso calc R 1 . . H H15 -0.0271 0.2293 0.2307 0.070 Uiso calc R 1 . . H H16 -0.0874 0.1495 0.2774 0.064 Uiso calc R 1 . . H H22 -0.2150 0.0273 0.3625 0.062 Uiso calc R 1 . . H H23 -0.2688 0.0056 0.1883 0.069 Uiso calc R 1 . . H H24 -0.3113 0.1053 -0.0219 0.106 Uiso calc R 1 . . H H25 -0.2623 0.1795 0.0871 0.062 Uiso calc R 1 . . H H26 -0.2090 0.2013 0.2623 0.059 Uiso calc R 1 . . H H32 -0.2813 0.1699 0.4632 0.067 Uiso calc R 1 . . H H33 -0.3417 0.1899 0.6285 0.071 Uiso calc R 1 . . H H34 -0.3530 0.1804 0.8422 0.108 Uiso calc R 1 . . H H35 -0.2124 0.1476 0.8596 0.080 Uiso calc R 1 . . H H36 -0.1523 0.1293 0.6939 0.076 Uiso calc R 1 . . H H42 0.0833 0.3136 0.5475 0.112 Uiso calc R 1 . . H H43 0.1352 0.3367 0.7235 0.137 Uiso calc R 1 . . H H44 0.1063 0.4164 0.8450 0.130 Uiso calc R 1 . . H H46 0.0333 0.5022 0.8825 0.125 Uiso calc R 1 . . H H47 -0.0480 0.5513 0.8244 0.130 Uiso calc R 1 . . H H49 -0.1310 0.5663 0.6721 0.130 Uiso calc R 1 . . H H410 -0.1758 0.5368 0.4923 0.138 Uiso calc R 1 . . H H411 -0.1367 0.4591 0.3803 0.114 Uiso calc R 1 . . H H51 0.0431 0.3206 0.2201 0.129 Uiso calc R 1 . . H H51A 0.0576 0.3000 -0.0130 0.130 Uiso d P 0.50 . . H H51B -0.0020 0.3055 0.0582 0.130 Uiso d P 0.50 . . H H51C 0.0336 0.3640 0.0249 0.130 Uiso d P 0.50 . . H H51D 0.0258 0.2823 0.0218 0.130 Uiso d P 0.50 . . H H51E 0.0019 0.3463 0.0597 0.130 Uiso d P 0.50 . . H H51F 0.0615 0.3408 -0.0115 0.130 Uiso d P 0.50 . . 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 C1 0.0434(11) 0.0421(11) 0.0405(13) 0.0008(9) -0.0022(10) 0.0013(10) C2 0.0634(13) 0.0551(13) 0.0601(17) 0.0066(11) -0.0050(12) 0.0053(12) C11 0.0398(11) 0.0459(11) 0.0348(13) 0.0001(9) 0.0002(10) 0.0000(10) C12 0.0490(11) 0.0558(13) 0.0365(13) -0.0018(10) 0.0088(10) -0.0021(11) C13 0.0619(13) 0.0483(12) 0.0438(14) -0.0100(11) 0.0080(12) -0.0058(11) C14 0.0575(13) 0.0612(14) 0.0391(14) -0.0198(11) 0.0062(12) -0.0030(12) O14 0.1103(13) 0.0897(12) 0.0636(13) -0.0553(10) 0.0359(11) -0.0190(10) C15 0.0549(13) 0.0776(16) 0.0425(14) -0.0150(11) 0.0172(11) -0.0090(13) C16 0.0544(12) 0.0571(13) 0.0483(15) -0.0084(11) 0.0129(12) -0.0130(11) C21 0.0467(11) 0.0419(11) 0.0376(13) -0.0009(9) 0.0056(10) 0.0008(11) C22 0.0630(13) 0.0441(12) 0.0491(15) -0.0061(10) 0.0011(12) 0.0030(11) C23 0.0665(14) 0.0485(13) 0.0572(16) -0.0142(11) 0.0021(13) -0.0060(12) C24 0.0539(13) 0.0614(14) 0.0366(14) -0.0117(11) 0.0041(11) -0.0098(12) O24 0.0859(11) 0.0816(11) 0.0453(11) -0.0203(10) -0.0076(9) -0.0106(9) C25 0.0622(13) 0.0547(13) 0.0370(13) -0.0078(11) -0.0013(12) 0.0035(11) C26 0.0591(13) 0.0440(12) 0.0442(14) -0.0097(10) 0.0001(11) -0.0031(11) C31 0.0433(11) 0.0473(12) 0.0368(14) -0.0051(9) -0.0003(10) 0.0059(10) C32 0.0545(13) 0.0795(15) 0.0335(13) 0.0103(11) -0.0033(11) 0.0045(12) C33 0.0487(12) 0.0856(16) 0.0429(15) 0.0137(11) -0.0037(12) -0.0004(13) C34 0.0479(13) 0.0663(14) 0.0388(15) -0.0057(11) 0.0026(11) 0.0001(12) O34 0.0544(9) 0.1226(13) 0.0398(10) 0.0026(10) 0.0050(8) -0.0052(9) C35 0.0514(13) 0.115(2) 0.0334(14) -0.0043(13) -0.0048(12) 0.0093(14) C36 0.0424(12) 0.1016(19) 0.0449(16) 0.0021(12) -0.0022(12) 0.0135(14) N41 0.0611(12) 0.0741(13) 0.0691(15) -0.0114(10) 0.0048(12) 0.0067(13) C42 0.0723(18) 0.105(2) 0.104(3) -0.0053(18) 0.016(2) 0.020(2) C43 0.069(2) 0.159(4) 0.114(3) -0.009(2) -0.002(2) 0.056(3) C44 0.078(2) 0.175(4) 0.073(3) -0.048(2) -0.016(2) 0.038(3) C45 0.0784(19) 0.105(2) 0.0546(19) -0.0466(17) -0.0034(16) 0.0126(18) C46 0.134(3) 0.121(3) 0.058(2) -0.071(2) 0.007(2) -0.017(2) C47 0.150(3) 0.082(2) 0.093(3) -0.045(2) 0.045(3) -0.023(2) C48 0.096(2) 0.0594(16) 0.082(2) -0.0229(16) 0.0248(19) 0.0002(17) C49 0.110(3) 0.070(2) 0.144(4) 0.006(2) 0.044(3) 0.021(2) C410 0.085(2) 0.099(3) 0.162(4) -0.003(2) 0.013(3) 0.050(3) C411 0.087(2) 0.089(2) 0.110(3) -0.0259(18) -0.022(2) 0.034(2) N412 0.0746(14) 0.0687(13) 0.0700(17) -0.0213(11) -0.0152(12) 0.0103(12) C413 0.0658(15) 0.0523(14) 0.0593(17) -0.0238(12) 0.0076(14) 0.0080(14) C414 0.0629(15) 0.0635(14) 0.0505(16) -0.0288(13) 0.0021(13) 0.0051(13) O51 0.0582(9) 0.1455(16) 0.0548(12) -0.0236(11) -0.0002(9) -0.0008(12) C51 0.097(2) 0.124(2) 0.060(2) -0.0228(17) -0.0107(17) 0.0039(17)