data_4000074 _journal_name_full 'Chemistry of Materials' _journal_year 2001 _chemical_name_common bis(guanidinium)(4,4'-biphenyldisulfonate).3(2 _chemical_formula_sum 'C25 H28 N3 O3 S' _chemical_formula_weight 450.56 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P2(1)/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.5509(7) _cell_length_b 25.493(2) _cell_length_c 12.0573(12) _cell_angle_alpha 90.00 _cell_angle_beta 91.574(2) _cell_angle_gamma 90.00 _cell_volume 2320.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2348 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 956 _exptl_absorpt_coefficient_mu 0.171 _exptl_absorpt_correction_type simulated psi-scans _exptl_absorpt_correction_T_min 0.9331 _exptl_absorpt_correction_T_max 0.9797 _exptl_absorpt_process_details 'SADABS, G. Sheldrick (1999)' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART platform CCD, Bruker _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12086 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0657 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4078 _reflns_number_gt 2475 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0462P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4078 _refine_ls_number_parameters 368 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0814 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.0950 _refine_ls_wR_factor_gt 0.0880 _refine_ls_goodness_of_fit_ref 0.852 _refine_ls_restrained_S_all 0.860 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.95261(7) 0.20737(2) 0.53550(5) 0.03568(17) Uani 1 1 d . . . O1 O 1.10847(18) 0.22843(6) 0.48177(11) 0.0401(4) Uani 1 1 d . . . N1 N 1.1113(2) 0.25483(7) 0.24989(15) 0.0464(5) Uani 1 1 d . . . H1A H 1.1138 0.2494 0.3220 0.056 Uiso 1 1 calc R . . H1B H 1.2109 0.2570 0.2140 0.056 Uiso 1 1 calc R . . C1 C 0.9655(3) 0.13861(8) 0.52420(17) 0.0326(5) Uani 1 1 d . . . O2 O 0.78925(18) 0.22319(5) 0.47768(11) 0.0392(4) Uani 1 1 d . . . N2 N 0.8079(2) 0.25654(7) 0.24905(15) 0.0433(5) Uani 1 1 d . . . H2A H 0.8101 0.2511 0.3212 0.052 Uiso 1 1 calc R . . H2B H 0.7058 0.2598 0.2127 0.052 Uiso 1 1 calc R . . C2 C 0.9044(3) 0.11315(9) 0.42974(19) 0.0452(6) Uani 1 1 d . . . H2 H 0.8525 0.1329 0.3704 0.054 Uiso 1 1 calc R . . O3 O 0.95307(18) 0.21934(5) 0.65349(11) 0.0392(4) Uani 1 1 d . . . N3 N 0.9543(2) 0.26787(7) 0.08677(15) 0.0431(5) Uani 1 1 d . . . H3A H 0.8523 0.2712 0.0504 0.052 Uiso 1 1 calc R . . H3B H 1.0541 0.2700 0.0510 0.052 Uiso 1 1 calc R . . C3 C 0.9178(3) 0.05933(9) 0.42049(18) 0.0442(6) Uani 1 1 d . . . H3 H 0.8742 0.0427 0.3548 0.053 Uiso 1 1 calc R . . C4 C 0.9935(3) 0.02888(8) 0.50489(17) 0.0324(5) Uani 1 1 d . . . C5 C 1.0560(3) 0.05546(9) 0.59865(19) 0.0494(7) Uani 1 1 d . . . H5 H 1.1101 0.0360 0.6577 0.059 Uiso 1 1 calc R . . C6 C 1.0422(3) 0.10901(9) 0.60864(19) 0.0488(7) Uani 1 1 d . . . H6 H 1.0857 0.1258 0.6742 0.059 Uiso 1 1 calc R . . C7 C 0.9576(3) 0.25973(8) 0.19543(19) 0.0361(6) Uani 1 1 d . . . C1A C 0.4255(3) 0.03879(7) 0.35271(13) 0.0389(11) Uani 0.754(3) 1 d PG A 1 H1A1 H 0.3707 0.0378 0.4226 0.047 Uiso 0.754(3) 1 calc PR A 1 C2A C 0.4613(3) 0.08672(6) 0.30314(15) 0.0448(12) Uani 0.754(3) 1 d PG A 1 C3A C 0.5416(3) 0.08819(6) 0.20082(16) 0.0438(12) Uani 0.754(3) 1 d PG A 1 C4A C 0.5861(3) 0.04172(7) 0.14807(14) 0.0410(12) Uani 0.754(3) 1 d PG A 1 H4A H 0.6410 0.0427 0.0781 0.049 Uiso 0.754(3) 1 calc PR A 1 C5A C 0.5503(2) -0.00620(6) 0.19764(12) 0.0329(11) Uani 0.754(3) 1 d PG A 1 C6A C 0.4700(2) -0.00767(6) 0.29996(12) 0.0390(11) Uani 0.754(3) 1 d PG A 1 C7A C 0.4342(3) -0.05560(7) 0.34954(16) 0.0476(13) Uani 0.754(3) 1 d PG A 1 H7A H 0.3794 -0.0566 0.4195 0.057 Uiso 0.754(3) 1 calc PR A 1 C8A C 0.4787(3) -0.10206(6) 0.2968(2) 0.0562(12) Uani 0.754(3) 1 d PG A 1 H8A H 0.4543 -0.1348 0.3307 0.067 Uiso 0.754(3) 1 calc PR A 1 C9A C 0.5590(3) -0.10060(6) 0.1945(2) 0.0539(12) Uani 0.754(3) 1 d PG A 1 H9A H 0.5895 -0.1324 0.1584 0.065 Uiso 0.754(3) 1 calc PR A 1 C10A C 0.5948(3) -0.05267(7) 0.14490(16) 0.0482(13) Uani 0.754(3) 1 d PG A 1 H10A H 0.6497 -0.0517 0.0750 0.058 Uiso 0.754(3) 1 calc PR A 1 C11A C 0.4111(4) 0.13759(7) 0.3618(2) 0.0688(16) Uani 0.754(3) 1 d PG A 1 H11A H 0.3574 0.1292 0.4328 0.103 Uiso 0.754(3) 1 calc PR A 1 H11B H 0.3262 0.1572 0.3150 0.103 Uiso 0.754(3) 1 calc PR A 1 H11C H 0.5176 0.1589 0.3753 0.103 Uiso 0.754(3) 1 calc PR A 1 C12A C 0.5708(4) 0.14046(7) 0.1409(2) 0.0738(16) Uani 0.754(3) 1 d PG A 1 H12A H 0.4585 0.1597 0.1351 0.111 Uiso 0.754(3) 1 calc PR A 1 H12B H 0.6141 0.1337 0.0664 0.111 Uiso 0.754(3) 1 calc PR A 1 H12C H 0.6583 0.1614 0.1829 0.111 Uiso 0.754(3) 1 calc PR A 1 C1B C 0.4348(8) 0.0023(2) 0.3583(4) 0.047(4) Uani 0.246(3) 1 d PG A 2 H1B1 H 0.3842 0.0009 0.4295 0.056 Uiso 0.246(3) 1 calc PR A 2 C2B C 0.4844(8) -0.0438(2) 0.3059(4) 0.052(4) Uani 0.246(3) 1 d PG A 2 C3B C 0.5584(8) -0.0417(2) 0.2017(4) 0.053(4) Uani 0.246(3) 1 d PG A 2 C4B C 0.5828(8) 0.0063(2) 0.1499(4) 0.037(4) Uani 0.246(3) 1 d PG A 2 H4B H 0.6333 0.0077 0.0787 0.045 Uiso 0.246(3) 1 calc PR A 2 C5B C 0.5331(7) 0.0524(2) 0.2024(4) 0.049(4) Uani 0.246(3) 1 d PG A 2 C6B C 0.4591(7) 0.0504(2) 0.3066(4) 0.032(3) Uani 0.246(3) 1 d PGU A 2 C7B C 0.4094(10) 0.0964(2) 0.3591(5) 0.058(4) Uani 0.246(3) 1 d PG A 2 H7B H 0.3589 0.0950 0.4303 0.070 Uiso 0.246(3) 1 calc PR A 2 C8B C 0.4338(11) 0.1445(2) 0.3073(6) 0.081(6) Uani 0.246(3) 1 d PG A 2 H8B H 0.3998 0.1760 0.3432 0.097 Uiso 0.246(3) 1 calc PR A 2 C9B C 0.5078(11) 0.1465(2) 0.2031(6) 0.082(6) Uani 0.246(3) 1 d PG A 2 H9B H 0.5244 0.1794 0.1677 0.099 Uiso 0.246(3) 1 calc PR A 2 C10B C 0.5574(10) 0.1005(2) 0.1506(5) 0.035(3) Uani 0.246(3) 1 d PG A 2 H10B H 0.6080 0.1019 0.0794 0.042 Uiso 0.246(3) 1 calc PR A 2 C11B C 0.4493(12) -0.0918(2) 0.3596(6) 0.054(4) Uani 0.246(3) 1 d PG A 2 H11D H 0.3779 -0.1143 0.3099 0.082 Uiso 0.246(3) 1 calc PR A 2 H11E H 0.3842 -0.0849 0.4273 0.082 Uiso 0.246(3) 1 calc PR A 2 H11F H 0.5613 -0.1094 0.3788 0.082 Uiso 0.246(3) 1 calc PR A 2 C12B C 0.6021(12) -0.0878(2) 0.1403(6) 0.063(5) Uani 0.246(3) 1 d PG A 2 H12D H 0.7015 -0.1059 0.1776 0.095 Uiso 0.246(3) 1 calc PR A 2 H12E H 0.6354 -0.0778 0.0652 0.095 Uiso 0.246(3) 1 calc PR A 2 H12F H 0.4992 -0.1112 0.1360 0.095 Uiso 0.246(3) 1 calc PR A 2 C1C C 0.9107(5) 0.03486(12) -0.1050(3) 0.066(3) Uani 0.50 1 d PG B 3 H1C H 0.8540 0.0362 -0.1763 0.079 Uiso 0.50 1 calc PR B 3 C2C C 0.9498(4) 0.08106(10) -0.0482(3) 0.048(2) Uani 0.50 1 d PG B 3 C3C C 1.0329(4) 0.07914(8) 0.0560(3) 0.057(2) Uani 0.50 1 d PG B 3 C4C C 1.0768(5) 0.03101(9) 0.1035(3) 0.048(2) Uani 0.50 1 d PGU B 3 H4C H 1.1335 0.0297 0.1747 0.057 Uiso 0.50 1 calc PR B 3 C5C C 1.0376(5) -0.01519(8) 0.0467(3) 0.052(2) Uani 0.50 1 d PG B 3 C6C C 0.9546(5) -0.01326(11) -0.0576(3) 0.052(2) Uani 0.50 1 d PGU B 3 C7C C 0.9155(6) -0.05946(13) -0.1144(4) 0.072(3) Uani 0.50 1 d PG B 3 H7C H 0.8587 -0.0581 -0.1856 0.086 Uiso 0.50 1 calc PR B 3 C8C C 0.9594(7) -0.10759(11) -0.0669(5) 0.084(3) Uani 0.50 1 d PG B 3 H8C H 0.9326 -0.1392 -0.1057 0.101 Uiso 0.50 1 calc PR B 3 C9C C 1.0424(7) -0.10951(8) 0.0374(5) 0.077(3) Uani 0.50 1 d PG B 3 H9C H 1.0724 -0.1424 0.0698 0.093 Uiso 0.50 1 calc PR B 3 C10C C 1.0815(6) -0.06331(9) 0.0941(4) 0.056(2) Uani 0.50 1 d PG B 3 H10C H 1.1383 -0.0646 0.1654 0.068 Uiso 0.50 1 calc PR B 3 C11C C 0.9110(5) 0.13349(12) -0.0993(3) 0.081(2) Uani 0.50 1 d PG B 3 H11G H 1.0226 0.1518 -0.1127 0.121 Uiso 0.50 1 calc PR B 3 H11H H 0.8399 0.1544 -0.0487 0.121 Uiso 0.50 1 calc PR B 3 H11I H 0.8452 0.1287 -0.1697 0.121 Uiso 0.50 1 calc PR B 3 C12C C 1.0714(5) 0.12828(9) 0.1219(3) 0.0699(18) Uani 0.50 1 d PG B 3 H12G H 1.1238 0.1188 0.1945 0.105 Uiso 0.50 1 calc PR B 3 H12H H 0.9610 0.1476 0.1324 0.105 Uiso 0.50 1 calc PR B 3 H12I H 1.1545 0.1503 0.0818 0.105 Uiso 0.50 1 calc PR B 3 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0281(3) 0.0465(3) 0.0325(3) 0.0004(3) 0.0014(2) 0.0015(3) O1 0.0308(9) 0.0535(9) 0.0361(9) 0.0053(7) 0.0007(7) -0.0044(7) N1 0.0290(12) 0.0741(14) 0.0359(12) 0.0133(10) 0.0005(9) 0.0010(10) C1 0.0235(12) 0.0473(13) 0.0269(12) -0.0005(11) 0.0007(9) 0.0022(11) O2 0.0283(9) 0.0512(9) 0.0380(9) 0.0023(7) -0.0015(7) 0.0055(7) N2 0.0296(11) 0.0629(13) 0.0374(12) 0.0094(10) -0.0002(9) -0.0025(9) C2 0.0515(16) 0.0500(16) 0.0337(14) 0.0059(12) -0.0099(12) 0.0080(12) O3 0.0370(9) 0.0500(10) 0.0306(9) -0.0035(7) 0.0011(7) 0.0023(7) N3 0.0297(11) 0.0647(13) 0.0350(12) 0.0073(10) 0.0007(9) -0.0011(10) C3 0.0539(16) 0.0490(15) 0.0292(13) -0.0026(11) -0.0101(12) 0.0022(12) C4 0.0213(12) 0.0476(12) 0.0285(12) 0.0007(11) 0.0022(9) 0.0011(11) C5 0.0610(18) 0.0479(16) 0.0379(15) -0.0001(12) -0.0208(13) 0.0071(13) C6 0.0568(17) 0.0501(16) 0.0386(15) -0.0061(12) -0.0181(13) 0.0045(13) C7 0.0341(15) 0.0364(13) 0.0378(15) 0.0053(11) 0.0002(12) -0.0026(10) C1A 0.027(2) 0.062(3) 0.027(2) 0.003(2) 0.0029(16) 0.000(2) C2A 0.028(2) 0.058(3) 0.047(3) -0.022(2) -0.0068(19) 0.001(2) C3A 0.032(2) 0.056(3) 0.043(3) 0.003(2) -0.005(2) -0.007(2) C4A 0.032(2) 0.053(3) 0.037(2) -0.008(2) -0.0003(17) -0.003(2) C5A 0.026(2) 0.039(2) 0.035(3) 0.0011(19) 0.0036(18) 0.0021(18) C6A 0.029(2) 0.051(3) 0.036(3) 0.000(2) -0.0058(19) 0.0053(18) C7A 0.039(3) 0.062(3) 0.041(3) 0.006(2) -0.003(2) 0.004(2) C8A 0.054(3) 0.046(2) 0.068(3) 0.011(2) -0.006(2) 0.002(2) C9A 0.057(3) 0.043(2) 0.061(3) -0.009(2) -0.010(2) 0.014(2) C10A 0.046(3) 0.050(3) 0.048(3) 0.004(2) -0.006(2) 0.000(2) C11A 0.059(3) 0.067(3) 0.079(4) -0.036(3) -0.003(3) 0.004(3) C12A 0.076(3) 0.047(3) 0.098(4) 0.007(3) 0.000(3) -0.002(2) C1B 0.044(8) 0.043(8) 0.053(9) 0.024(7) -0.020(6) 0.000(6) C2B 0.025(7) 0.107(13) 0.025(8) 0.010(8) 0.000(6) 0.004(7) C3B 0.040(8) 0.100(13) 0.018(7) 0.007(7) -0.014(6) 0.001(8) C4B 0.021(6) 0.052(8) 0.040(8) -0.004(6) 0.012(5) -0.025(6) C5B 0.052(8) 0.029(7) 0.064(10) 0.002(7) -0.026(7) -0.008(6) C6B 0.032(5) 0.027(6) 0.036(6) 0.014(5) 0.007(5) -0.018(5) C7B 0.060(9) 0.056(9) 0.057(9) 0.003(8) -0.033(7) 0.007(7) C8B 0.067(11) 0.135(14) 0.041(9) -0.025(9) -0.020(8) 0.044(10) C9B 0.073(11) 0.056(9) 0.116(15) 0.038(9) -0.049(11) -0.014(7) C10B 0.040(7) 0.033(7) 0.032(7) 0.006(6) -0.005(5) 0.020(5) C11B 0.033(7) 0.088(11) 0.043(8) -0.012(8) 0.005(6) -0.003(7) C12B 0.035(7) 0.119(14) 0.035(8) 0.020(8) 0.000(6) -0.011(8) C1C 0.032(4) 0.135(9) 0.032(4) -0.024(5) 0.004(3) -0.020(5) C2C 0.033(4) 0.081(7) 0.029(4) 0.005(5) -0.003(3) -0.001(4) C3C 0.038(4) 0.089(6) 0.043(5) -0.023(4) 0.002(3) -0.005(4) C4C 0.027(3) 0.092(6) 0.023(4) -0.014(4) -0.008(3) -0.002(4) C5C 0.029(4) 0.099(7) 0.030(4) -0.022(4) 0.001(3) -0.005(4) C6C 0.027(3) 0.106(6) 0.021(4) -0.024(4) -0.009(3) -0.012(4) C7C 0.034(4) 0.131(8) 0.051(5) -0.040(5) 0.001(3) -0.007(5) C8C 0.045(4) 0.138(8) 0.070(6) -0.068(6) -0.014(4) -0.004(5) C9C 0.064(5) 0.079(7) 0.089(6) -0.007(5) -0.006(4) 0.011(5) C10C 0.033(4) 0.107(7) 0.029(4) -0.026(4) -0.012(3) -0.001(4) C11C 0.059(4) 0.106(5) 0.077(5) 0.019(4) -0.011(4) -0.005(4) C12C 0.051(4) 0.094(5) 0.063(4) -0.001(4) -0.020(3) 0.001(4)