data_2002979 _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'-Sulfonyldiphenol--1,10-phenanthroline (2/3) ; _chemical_name_common ? _chemical_formula_moiety '2(C12 H10 O4 S), 3(C12 H8 N2)' _chemical_formula_sum 'C60 H44 N6 O8 S2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_weight 1041.13 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.8692(16) _cell_length_b 24.3728(17) _cell_length_c 13.0952(9) _cell_angle_alpha 90.00 _cell_angle_beta 102.362(8) _cell_angle_gamma 90.00 _cell_volume 4947.5(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.21 _cell_measurement_theta_max 18.28 _cell_measurement_temperature 294.0(10) _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.10 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method ? _exptl_crystal_F_000 2168 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'ABSORB in NRCVAX (Gabe et al., 1989)' _exptl_absorpt_correction_T_min .9367 _exptl_absorpt_correction_T_max .9833 _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 4636 _diffrn_reflns_av_R_equivalents 0.006 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.14 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1.7 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 -9 2 3 1 5 0 -4 6 _reflns_number_total 4434 _reflns_number_gt 3182 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1040 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_number_reflns 4434 _refine_ls_number_parameters 346 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+1.3074P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.221 _refine_diff_density_min -0.298 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00124(18) 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 0.30076(3) 0.51893(2) 0.06788(4) 0.03971(16) Uani d . 1 . . S O11 0.21571(9) 0.50137(6) 0.07611(13) 0.0542(4) Uani d . 1 . . O O12 0.31144(10) 0.53995(6) -0.03161(11) 0.0537(4) Uani d . 1 . . O O14 0.52449(9) 0.32527(6) 0.14013(13) 0.0519(4) Uani d . 1 . . O O24 0.40470(15) 0.68772(7) 0.38834(14) 0.0788(6) Uani d . 1 . . O C11 0.36983(12) 0.46251(7) 0.10120(15) 0.0348(4) Uani d . 1 . . C C12 0.33602(13) 0.41287(8) 0.12514(15) 0.0366(5) Uani d . 1 . . C C13 0.38733(13) 0.36666(8) 0.14025(16) 0.0410(5) Uani d . 1 . . C C14 0.47214(13) 0.36959(8) 0.12947(16) 0.0400(5) Uani d . 1 . . C C15 0.50681(14) 0.41987(8) 0.11007(17) 0.0438(5) Uani d . 1 . . C C16 0.45568(14) 0.46615(8) 0.09618(16) 0.0419(5) Uani d . 1 . . C C21 0.33627(12) 0.56929(7) 0.16260(16) 0.0373(5) Uani d . 1 . . C C22 0.32840(15) 0.56028(8) 0.26461(18) 0.0486(6) Uani d . 1 . . C C23 0.35180(16) 0.60072(9) 0.33827(18) 0.0545(6) Uani d . 1 . . C C24 0.38339(15) 0.65037(8) 0.31102(18) 0.0500(6) Uani d . 1 . . C C25 0.39243(14) 0.65918(8) 0.20995(18) 0.0464(5) Uani d . 1 . . C C26 0.36950(13) 0.61855(8) 0.13610(17) 0.0427(5) Uani d . 1 . . C N31 0.43551(11) 0.22495(6) 0.15909(14) 0.0454(5) Uani d . 1 . . N C32 0.46443(12) 0.17660(7) 0.20493(16) 0.0366(5) Uani d . 1 . . C C33 0.42827(13) 0.12595(8) 0.16557(17) 0.0435(5) Uani d . 1 . . C C34 0.35779(14) 0.12676(9) 0.08027(19) 0.0525(6) Uani d . 1 . . C C35 0.32814(15) 0.17518(10) 0.0368(2) 0.0594(7) Uani d . 1 . . C C36 0.37003(15) 0.22315(9) 0.07717(19) 0.0571(6) Uani d . 1 . . C C37 0.46525(16) 0.07569(8) 0.21074(19) 0.0561(6) Uani d . 1 . . C N41 0.39058(13) 0.79510(7) 0.29143(16) 0.0587(5) Uani d . 1 . . N C42 0.43405(14) 0.83940(8) 0.33762(17) 0.0432(5) Uani d . 1 . . C C43 0.40639(13) 0.89354(8) 0.31043(17) 0.0430(5) Uani d . 1 . . C C44 0.33280(15) 0.90033(10) 0.23003(19) 0.0543(6) Uani d . 1 . . C C45 0.28969(16) 0.85595(11) 0.1843(2) 0.0650(7) Uani d . 1 . . C C46 0.32111(17) 0.80426(11) 0.2181(2) 0.0696(7) Uani d . 1 . . C C47 0.45315(15) 0.93845(9) 0.36505(19) 0.0509(6) Uani d . 1 . . C N51 0.53579(13) 0.77841(7) 0.44305(17) 0.0573(5) Uani d . 1 . . N C52 0.50987(13) 0.83069(8) 0.41960(17) 0.0437(5) Uani d . 1 . . C C53 0.55290(13) 0.87631(8) 0.47196(18) 0.0453(5) Uani d . 1 . . C C54 0.62420(15) 0.86635(10) 0.5533(2) 0.0585(6) Uani d . 1 . . C C55 0.64958(16) 0.81401(11) 0.5777(2) 0.0700(8) Uani d . 1 . . C C56 0.60375(17) 0.77131(10) 0.5201(2) 0.0696(8) Uani d . 1 . . C C57 0.52271(15) 0.93050(9) 0.44202(19) 0.0521(6) Uani d . 1 . . C H14 0.4977 0.2981 0.1519 0.078 Uiso calc R 1 . . H H24 0.4147 0.7173 0.3635 0.118 Uiso calc R 1 . . H H12 0.2787 0.4107 0.1310 0.044 Uiso calc R 1 . . H H13 0.3650 0.3335 0.1577 0.049 Uiso calc R 1 . . H H15 0.5646 0.4223 0.1064 0.053 Uiso calc R 1 . . H H16 0.4790 0.4998 0.0834 0.050 Uiso calc R 1 . . H H22 0.3073 0.5270 0.2831 0.058 Uiso calc R 1 . . H H23 0.3464 0.5947 0.4067 0.065 Uiso calc R 1 . . H H25 0.4139 0.6924 0.1917 0.056 Uiso calc R 1 . . H H26 0.3764 0.6242 0.0681 0.051 Uiso calc R 1 . . H H34 0.3316 0.0941 0.0537 0.063 Uiso calc R 1 . . H H35 0.2807 0.1765 -0.0189 0.071 Uiso calc R 1 . . H H36 0.3508 0.2561 0.0445 0.069 Uiso calc R 1 . . H H37 0.4406 0.0425 0.1851 0.067 Uiso calc R 1 . . H H44 0.3138 0.9354 0.2083 0.065 Uiso calc R 1 . . H H45 0.2403 0.8598 0.1318 0.078 Uiso calc R 1 . . H H46 0.2908 0.7739 0.1865 0.083 Uiso calc R 1 . . H H47 0.4350 0.9741 0.3468 0.061 Uiso calc R 1 . . H H54 0.6540 0.8955 0.5904 0.070 Uiso calc R 1 . . H H55 0.6967 0.8067 0.6318 0.084 Uiso calc R 1 . . H H56 0.6222 0.7356 0.5371 0.084 Uiso calc R 1 . . H H57 0.5517 0.9606 0.4764 0.062 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 0.0414(3) 0.0326(3) 0.0410(3) 0.0001(2) -0.0006(2) -0.0005(2) O11 0.0388(8) 0.0420(8) 0.0766(12) -0.0023(7) 0.0010(7) -0.0023(8) O12 0.0722(10) 0.0470(9) 0.0366(9) 0.0024(7) -0.0001(7) 0.0064(7) O14 0.0527(9) 0.0367(8) 0.0617(11) 0.0067(7) 0.0017(8) -0.0053(8) O24 0.1305(17) 0.0460(10) 0.0591(12) -0.0276(11) 0.0183(11) -0.0170(9) C11 0.0391(11) 0.0315(10) 0.0314(11) -0.0018(8) 0.0019(8) -0.0023(8) C12 0.0370(11) 0.0362(11) 0.0350(12) -0.0033(8) 0.0041(9) -0.0001(9) C13 0.0479(12) 0.0313(10) 0.0404(12) -0.0068(9) 0.0020(9) 0.0010(9) C14 0.0450(12) 0.0352(10) 0.0361(12) 0.0038(9) 0.0003(9) -0.0042(9) C15 0.0391(11) 0.0461(12) 0.0460(13) 0.0005(9) 0.0090(10) -0.0008(10) C16 0.0485(12) 0.0348(11) 0.0422(12) -0.0066(9) 0.0091(10) 0.0017(9) C21 0.0397(11) 0.0300(10) 0.0402(12) 0.0022(8) 0.0042(9) 0.0004(9) C22 0.0637(14) 0.0320(11) 0.0500(14) -0.0088(10) 0.0118(11) 0.0027(10) C23 0.0807(17) 0.0419(12) 0.0413(13) -0.0106(12) 0.0137(12) -0.0018(10) C24 0.0618(14) 0.0356(11) 0.0487(14) -0.0047(10) 0.0034(11) -0.0069(10) C25 0.0547(13) 0.0300(11) 0.0520(14) -0.0051(9) 0.0060(11) 0.0067(10) C26 0.0487(12) 0.0366(11) 0.0413(12) -0.0025(9) 0.0064(10) 0.0038(9) N31 0.0465(10) 0.0316(9) 0.0516(11) 0.0020(7) -0.0038(9) -0.0004(8) C32 0.0403(11) 0.0278(10) 0.0416(12) 0.0011(8) 0.0085(9) -0.0011(9) C33 0.0489(12) 0.0347(11) 0.0465(13) -0.0044(9) 0.0096(10) -0.0045(9) C34 0.0501(13) 0.0454(13) 0.0577(15) -0.0101(10) 0.0020(11) -0.0098(11) C35 0.0508(14) 0.0544(14) 0.0619(16) -0.0010(11) -0.0128(12) -0.0085(12) C36 0.0556(14) 0.0451(13) 0.0603(16) 0.0066(11) -0.0108(12) 0.0005(11) C37 0.0767(17) 0.0264(10) 0.0609(16) -0.0073(10) 0.0055(12) -0.0030(10) N41 0.0599(12) 0.0434(11) 0.0673(14) -0.0075(9) 0.0014(11) -0.0071(10) C42 0.0479(12) 0.0352(11) 0.0479(13) -0.0031(9) 0.0132(10) -0.0027(9) C43 0.0458(12) 0.0402(11) 0.0463(13) 0.0041(9) 0.0168(10) 0.0030(10) C44 0.0547(14) 0.0569(14) 0.0517(15) 0.0106(11) 0.0124(11) 0.0066(12) C45 0.0531(15) 0.0798(19) 0.0560(16) 0.0043(13) -0.0016(12) -0.0030(14) C46 0.0638(16) 0.0644(17) 0.0720(19) -0.0140(13) -0.0044(14) -0.0117(14) C47 0.0588(14) 0.0311(11) 0.0658(16) 0.0044(10) 0.0197(12) 0.0041(11) N51 0.0591(12) 0.0361(10) 0.0745(15) 0.0017(9) 0.0093(11) 0.0089(10) C52 0.0454(12) 0.0343(11) 0.0525(14) -0.0013(9) 0.0128(10) 0.0030(10) C53 0.0424(12) 0.0418(12) 0.0523(14) -0.0049(9) 0.0115(10) 0.0008(10) C54 0.0468(13) 0.0615(15) 0.0642(17) -0.0138(11) 0.0056(12) -0.0003(13) C55 0.0476(14) 0.0744(18) 0.081(2) -0.0006(13) -0.0023(13) 0.0232(15) C56 0.0624(16) 0.0514(15) 0.092(2) 0.0076(12) 0.0096(15) 0.0245(14) C57 0.0571(14) 0.0364(12) 0.0631(16) -0.0073(10) 0.0136(12) -0.0077(11)