data_4000421 _journal_name_full 'Chemistry of Materials' _journal_year 2004 _chemical_name_common 'guanidinium tetradecylbenzenesulfonate' _chemical_formula_sum 'C21 H39 N3 O3 S' _chemical_formula_weight 413.61 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.8868(8) _cell_length_b 10.1325(10) _cell_length_c 59.017(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.131(2) _cell_angle_gamma 90.00 _cell_volume 4713.0(8) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3307 _cell_measurement_theta_min 4.523 _cell_measurement_theta_max 51.417 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.166 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1808 _exptl_absorpt_coefficient_mu 0.162 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.712407 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'SADABS, R. Blessing, 1995' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART Platform CCD' _diffrn_measurement_method 'area detector, omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28804 _diffrn_reflns_av_R_equivalents 0.0776 _diffrn_reflns_av_sigmaI/netI 0.1075 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -75 _diffrn_reflns_limit_l_max 53 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 27.12 _reflns_number_total 10302 _reflns_number_gt 6158 _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^)+(0.0614P)^2^+9.7073P] 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 10302 _refine_ls_number_parameters 507 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1553 _refine_ls_R_factor_gt 0.0973 _refine_ls_wR_factor_ref 0.2372 _refine_ls_wR_factor_gt 0.2173 _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_restrained_S_all 1.135 _refine_ls_shift/su_max 0.000 _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 0.51252(13) 0.52493(11) 0.036165(18) 0.0245(3) Uani 1 1 d . . . S2 S 0.01547(14) 0.93036(11) 0.052047(19) 0.0278(3) Uani 1 1 d . . . O1 O 0.3597(4) 0.4450(3) 0.03341(5) 0.0292(7) Uani 1 1 d . . . O2 O 0.6620(4) 0.4453(3) 0.03207(5) 0.0291(7) Uani 1 1 d . . . O3 O -0.1390(4) 0.8648(3) 0.04408(5) 0.0324(8) Uani 1 1 d . . . O4 O 0.1655(4) 0.8708(3) 0.04268(5) 0.0322(8) Uani 1 1 d . . . C5 C 0.5275(5) 0.5656(4) 0.06482(7) 0.0244(9) Uani 1 1 d . . . O6 O 0.5037(4) 0.6472(3) 0.02366(5) 0.0333(8) Uani 1 1 d . . . N7 N 0.8536(4) 0.7035(4) 0.00316(6) 0.0298(9) Uani 1 1 d . . . H7A H 0.7552 0.6792 -0.0030 0.036 Uiso 1 1 calc R . . H7B H 0.8571 0.7540 0.0153 0.036 Uiso 1 1 calc R . . N8 N 0.9898(5) 0.5884(4) -0.02399(6) 0.0286(9) Uani 1 1 d . . . H8A H 0.8914 0.5641 -0.0302 0.034 Uiso 1 1 calc R . . H8B H 1.0847 0.5621 -0.0300 0.034 Uiso 1 1 calc R . . N9 N 1.1440(4) 0.7029(4) 0.00331(6) 0.0289(9) Uani 1 1 d . . . H9A H 1.1477 0.7548 0.0153 0.035 Uiso 1 1 calc R . . H9B H 1.2388 0.6766 -0.0027 0.035 Uiso 1 1 calc R . . N10 N 0.6570(5) 1.1629(4) 0.04156(7) 0.0365(10) Uani 1 1 d . . . H10A H 0.6561 1.2498 0.0415 0.044 Uiso 1 1 calc R . . H10B H 0.7541 1.1201 0.0416 0.044 Uiso 1 1 calc R . . C11 C 0.6361(6) 0.4975(5) 0.08002(8) 0.0346(11) Uani 1 1 d . . . H11 H 0.7041 0.4276 0.0747 0.042 Uiso 1 1 calc R . . C12 C 0.9366(6) 0.6573(5) 0.25513(8) 0.0340(11) Uani 1 1 d . . . H12A H 0.8226 0.6460 0.2613 0.041 Uiso 1 1 calc R . . H12B H 0.9575 0.7532 0.2537 0.041 Uiso 1 1 calc R . . C13 C 0.9952(6) 0.6643(4) -0.00574(7) 0.0246(10) Uani 1 1 d . . . C14 C 0.8055(6) 0.6543(5) 0.21542(8) 0.0359(11) Uani 1 1 d . . . H14A H 0.8282 0.7499 0.2138 0.043 Uiso 1 1 calc R . . H14B H 0.6921 0.6446 0.2219 0.043 Uiso 1 1 calc R . . O15 O 0.0118(4) 1.0716(3) 0.04896(6) 0.0373(8) Uani 1 1 d . . . C16 C 0.5556(7) 0.6739(5) 0.13559(8) 0.0384(12) Uani 1 1 d . . . H16A H 0.4391 0.6712 0.1413 0.046 Uiso 1 1 calc R . . H16B H 0.5927 0.7672 0.1360 0.046 Uiso 1 1 calc R . . C17 C 0.9362(6) 0.5963(5) 0.23187(8) 0.0362(12) Uani 1 1 d . . . H17A H 0.9150 0.5004 0.2333 0.043 Uiso 1 1 calc R . . H17B H 1.0501 0.6076 0.2256 0.043 Uiso 1 1 calc R . . C18 C 0.0743(6) 0.8507(5) 0.12781(8) 0.0337(11) Uani 1 1 d . . . C19 C 1.0640(6) 0.6607(5) 0.29521(8) 0.0374(12) Uani 1 1 d . . . H19A H 0.9478 0.6524 0.3008 0.045 Uiso 1 1 calc R . . H19B H 1.0896 0.7560 0.2940 0.045 Uiso 1 1 calc R . . C20 C 0.6209(7) 0.9057(5) 0.28727(8) 0.0380(12) Uani 1 1 d . . . H20A H 0.5997 1.0017 0.2884 0.046 Uiso 1 1 calc R . . H20B H 0.7364 0.8934 0.2816 0.046 Uiso 1 1 calc R . . N21 N 0.3685(5) 1.1616(4) 0.04156(8) 0.0427(11) Uani 1 1 d . . . H21A H 0.2721 1.1181 0.0421 0.051 Uiso 1 1 calc R . . H21B H 0.3682 1.2483 0.0410 0.051 Uiso 1 1 calc R . . C22 C 0.4934(6) 0.8460(5) 0.27053(8) 0.0369(12) Uani 1 1 d . . . H22A H 0.3784 0.8564 0.2765 0.044 Uiso 1 1 calc R . . H22B H 0.5164 0.7503 0.2693 0.044 Uiso 1 1 calc R . . C23 C 0.6695(6) 0.5975(5) 0.15206(8) 0.0331(11) Uani 1 1 d . . . H23A H 0.7861 0.5960 0.1464 0.040 Uiso 1 1 calc R . . H23B H 0.6290 0.5051 0.1528 0.040 Uiso 1 1 calc R . . C24 C 0.0901(7) 0.8184(5) 0.15271(8) 0.0390(12) Uani 1 1 d . . . H24A H 0.1156 0.7231 0.1542 0.047 Uiso 1 1 calc R . . H24B H -0.0219 0.8333 0.1593 0.047 Uiso 1 1 calc R . . C25 C 0.2296(6) 0.8414(5) 0.19119(8) 0.0368(12) Uani 1 1 d . . . H25A H 0.1167 0.8536 0.1977 0.044 Uiso 1 1 calc R . . H25B H 0.2524 0.7454 0.1907 0.044 Uiso 1 1 calc R . . C26 C 0.8014(6) 0.5919(5) 0.19205(8) 0.0357(11) Uani 1 1 d . . . H26A H 0.9158 0.5982 0.1858 0.043 Uiso 1 1 calc R . . H26B H 0.7733 0.4971 0.1935 0.043 Uiso 1 1 calc R . . C27 C 0.5468(6) 0.6308(4) 0.11129(7) 0.0278(10) Uani 1 1 d . . . C28 C 1.0675(6) 0.6001(5) 0.27191(8) 0.0371(12) Uani 1 1 d . . . H28A H 1.0479 0.5039 0.2732 0.045 Uiso 1 1 calc R . . H28B H 1.1818 0.6129 0.2659 0.045 Uiso 1 1 calc R . . C29 C 0.6742(6) 0.6558(5) 0.17561(8) 0.0341(11) Uani 1 1 d . . . H29A H 0.5598 0.6481 0.1818 0.041 Uiso 1 1 calc R . . H29B H 0.7011 0.7510 0.1745 0.041 Uiso 1 1 calc R . . C30 C 0.6122(6) 0.8437(5) 0.31086(8) 0.0367(12) Uani 1 1 d . . . H30A H 0.4949 0.8526 0.3161 0.044 Uiso 1 1 calc R . . H30B H 0.6373 0.7483 0.3097 0.044 Uiso 1 1 calc R . . C31 C 0.5128(6) 1.0969(5) 0.04162(8) 0.0347(11) Uani 1 1 d . . . C32 C 1.1783(7) 0.6591(5) 0.33594(9) 0.0413(12) Uani 1 1 d . . . H32A H 1.0594 0.6546 0.3407 0.050 Uiso 1 1 calc R . . H32B H 1.2102 0.7535 0.3352 0.050 Uiso 1 1 calc R . . C33 C 0.4956(7) 0.9069(5) 0.24708(8) 0.0374(12) Uani 1 1 d . . . H33A H 0.4739 1.0028 0.2483 0.045 Uiso 1 1 calc R . . H33B H 0.6099 0.8952 0.2410 0.045 Uiso 1 1 calc R . . C34 C 0.7336(7) 0.9044(5) 0.32859(8) 0.0379(12) Uani 1 1 d . . . H34A H 0.8515 0.8914 0.3239 0.046 Uiso 1 1 calc R . . H34B H 0.7124 1.0006 0.3294 0.046 Uiso 1 1 calc R . . C35 C 0.3619(7) 0.9056(5) 0.20692(8) 0.0388(12) Uani 1 1 d . . . H35A H 0.3380 1.0013 0.2079 0.047 Uiso 1 1 calc R . . H35B H 0.4750 0.8948 0.2004 0.047 Uiso 1 1 calc R . . C36 C 0.3655(6) 0.8469(5) 0.23078(8) 0.0371(12) Uani 1 1 d . . . H36A H 0.2519 0.8577 0.2371 0.044 Uiso 1 1 calc R . . H36B H 0.3880 0.7510 0.2297 0.044 Uiso 1 1 calc R . . C37 C 0.0334(5) 0.9012(4) 0.08143(8) 0.0262(10) Uani 1 1 d . . . C38 C 0.6454(6) 0.5308(5) 0.10266(8) 0.0337(11) Uani 1 1 d . . . H38 H 0.7214 0.4840 0.1126 0.040 Uiso 1 1 calc R . . C39 C 1.1873(7) 0.6000(5) 0.31250(8) 0.0408(12) Uani 1 1 d . . . H39A H 1.3040 0.6110 0.3072 0.049 Uiso 1 1 calc R . . H39B H 1.1642 0.5042 0.3134 0.049 Uiso 1 1 calc R . . C40 C 0.4291(6) 0.6662(5) 0.07336(8) 0.0362(12) Uani 1 1 d . . . H40 H 0.3533 0.7136 0.0635 0.043 Uiso 1 1 calc R . . C41 C 0.7155(7) 0.8455(5) 0.35188(8) 0.0399(12) Uani 1 1 d . . . H41A H 0.7400 0.7498 0.3510 0.048 Uiso 1 1 calc R . . H41B H 0.5958 0.8549 0.3561 0.048 Uiso 1 1 calc R . . C42 C 0.2223(6) 0.8938(5) 0.16703(8) 0.0364(12) Uani 1 1 d . . . H42A H 0.3349 0.8842 0.1604 0.044 Uiso 1 1 calc R . . H42B H 0.1929 0.9888 0.1671 0.044 Uiso 1 1 calc R . . C43 C -0.0152(7) 0.7677(6) 0.11342(9) 0.0476(14) Uani 1 1 d . . . H43 H -0.0647 0.6909 0.1196 0.057 Uiso 1 1 calc R . . C44 C 0.1441(7) 0.9619(5) 0.11818(9) 0.0446(14) Uani 1 1 d . . . H44 H 0.2064 1.0223 0.1276 0.054 Uiso 1 1 calc R . . N45 N 0.5150(6) 0.9669(4) 0.04252(8) 0.0465(12) Uani 1 1 d . . . H45A H 0.4192 0.9227 0.0431 0.056 Uiso 1 1 calc R . . H45B H 0.6123 0.9243 0.0426 0.056 Uiso 1 1 calc R . . C46 C 1.2920(7) 0.5917(5) 0.35388(8) 0.0410(13) Uani 1 1 d . . . H46A H 1.2593 0.4976 0.3548 0.049 Uiso 1 1 calc R . . H46B H 1.4107 0.5955 0.3490 0.049 Uiso 1 1 calc R . . C47 C 0.1251(7) 0.9867(5) 0.09529(9) 0.0410(12) Uani 1 1 d . . . H47 H 0.1754 1.0630 0.0890 0.049 Uiso 1 1 calc R . . C48 C 0.4403(7) 0.6979(5) 0.09604(8) 0.0391(12) Uani 1 1 d . . . H48 H 0.3728 0.7681 0.1014 0.047 Uiso 1 1 calc R . . C49 C 0.8268(7) 0.9035(5) 0.37074(8) 0.0393(12) Uani 1 1 d . . . H49A H 0.8088 1.0002 0.3711 0.047 Uiso 1 1 calc R . . H49B H 0.9471 0.8878 0.3673 0.047 Uiso 1 1 calc R . . C50 C 0.7944(8) 0.8475(6) 0.39395(9) 0.0492(14) Uani 1 1 d . . . H50A H 0.6769 0.8704 0.3979 0.059 Uiso 1 1 calc R . . H50B H 0.8013 0.7501 0.3931 0.059 Uiso 1 1 calc R . . C51 C -0.0370(7) 0.7896(5) 0.09064(9) 0.0440(14) Uani 1 1 d . . . H51 H -0.0996 0.7291 0.0813 0.053 Uiso 1 1 calc R . . C52 C 1.2837(7) 0.6513(6) 0.37689(9) 0.0501(14) Uani 1 1 d . . . H52A H 1.1635 0.6548 0.3811 0.060 Uiso 1 1 calc R . . H52B H 1.3258 0.7433 0.3762 0.060 Uiso 1 1 calc R . . C53 C 1.3846(9) 0.5784(7) 0.39527(10) 0.0681(19) Uani 1 1 d . . . H53A H 1.3390 0.4890 0.3968 0.102 Uiso 1 1 calc R . . H53B H 1.3765 0.6256 0.4097 0.102 Uiso 1 1 calc R . . H53C H 1.5038 0.5733 0.3912 0.102 Uiso 1 1 calc R . . C54 C 0.9118(8) 0.8932(7) 0.41276(10) 0.0626(18) Uani 1 1 d . . . H54A H 1.0290 0.8728 0.4091 0.094 Uiso 1 1 calc R . . H54B H 0.8840 0.8481 0.4268 0.094 Uiso 1 1 calc R . . H54C H 0.8995 0.9887 0.4147 0.094 Uiso 1 1 calc R . . 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 0.0162(5) 0.0324(6) 0.0248(6) -0.0007(5) -0.0019(4) 0.0006(5) S2 0.0232(6) 0.0330(6) 0.0270(6) -0.0007(5) -0.0014(4) 0.0016(5) O1 0.0175(16) 0.0372(18) 0.0325(17) -0.0055(14) -0.0021(13) -0.0015(13) O2 0.0182(16) 0.0382(18) 0.0308(17) -0.0049(14) -0.0008(13) 0.0035(13) O3 0.0227(17) 0.0427(19) 0.0314(18) -0.0077(15) -0.0049(13) -0.0002(15) O4 0.0205(17) 0.046(2) 0.0305(18) -0.0076(15) 0.0003(13) 0.0061(14) C5 0.015(2) 0.029(2) 0.029(2) 0.0015(19) -0.0035(17) -0.0026(18) O6 0.0290(18) 0.0373(18) 0.0337(18) 0.0073(15) 0.0013(14) -0.0004(15) N7 0.017(2) 0.045(2) 0.027(2) -0.0061(17) -0.0010(16) 0.0018(17) N8 0.0160(19) 0.036(2) 0.033(2) -0.0042(17) -0.0018(16) 0.0012(17) N9 0.0154(19) 0.043(2) 0.029(2) -0.0085(17) -0.0002(16) 0.0000(17) N10 0.022(2) 0.033(2) 0.054(3) 0.007(2) 0.0027(18) 0.0033(18) C11 0.031(3) 0.032(3) 0.041(3) -0.006(2) -0.004(2) 0.010(2) C12 0.033(3) 0.038(3) 0.031(3) 0.003(2) -0.001(2) 0.002(2) C13 0.023(2) 0.026(2) 0.025(2) 0.0041(18) -0.0007(18) 0.0001(19) C14 0.036(3) 0.043(3) 0.029(3) 0.002(2) 0.003(2) 0.001(2) O15 0.040(2) 0.0309(18) 0.041(2) 0.0109(15) -0.0046(16) 0.0036(16) C16 0.042(3) 0.040(3) 0.033(3) -0.004(2) -0.005(2) 0.003(2) C17 0.040(3) 0.038(3) 0.031(3) -0.001(2) 0.000(2) -0.001(2) C18 0.029(3) 0.037(3) 0.035(3) -0.002(2) 0.001(2) 0.003(2) C19 0.036(3) 0.043(3) 0.033(3) -0.002(2) -0.001(2) -0.001(2) C20 0.040(3) 0.038(3) 0.035(3) -0.001(2) -0.003(2) 0.001(2) N21 0.025(2) 0.038(2) 0.065(3) 0.014(2) -0.003(2) 0.0001(19) C22 0.034(3) 0.040(3) 0.036(3) -0.001(2) -0.004(2) 0.001(2) C23 0.035(3) 0.035(3) 0.029(3) 0.002(2) 0.000(2) -0.002(2) C24 0.040(3) 0.045(3) 0.033(3) 0.004(2) 0.000(2) -0.001(2) C25 0.039(3) 0.041(3) 0.030(3) 0.000(2) 0.000(2) 0.005(2) C26 0.040(3) 0.042(3) 0.025(2) 0.000(2) 0.000(2) -0.002(2) C27 0.027(2) 0.030(2) 0.027(2) -0.0020(19) -0.0023(19) -0.002(2) C28 0.038(3) 0.039(3) 0.034(3) 0.001(2) -0.002(2) -0.003(2) C29 0.034(3) 0.038(3) 0.030(3) 0.000(2) 0.002(2) -0.002(2) C30 0.039(3) 0.035(3) 0.035(3) -0.004(2) -0.003(2) -0.001(2) C31 0.034(3) 0.037(3) 0.033(3) 0.007(2) 0.001(2) 0.002(2) C32 0.040(3) 0.043(3) 0.040(3) 0.001(2) -0.004(2) 0.000(2) C33 0.039(3) 0.040(3) 0.033(3) -0.002(2) 0.003(2) 0.000(2) C34 0.039(3) 0.038(3) 0.036(3) 0.000(2) -0.005(2) -0.002(2) C35 0.045(3) 0.037(3) 0.034(3) -0.003(2) 0.002(2) 0.002(2) C36 0.039(3) 0.041(3) 0.031(3) -0.001(2) -0.001(2) -0.002(2) C37 0.021(2) 0.029(2) 0.029(2) -0.0020(19) 0.0009(18) -0.0002(19) C38 0.038(3) 0.029(3) 0.033(3) -0.002(2) -0.007(2) 0.003(2) C39 0.040(3) 0.044(3) 0.038(3) -0.001(2) -0.005(2) 0.000(2) C40 0.036(3) 0.036(3) 0.036(3) 0.001(2) -0.003(2) 0.012(2) C41 0.045(3) 0.038(3) 0.036(3) 0.001(2) -0.008(2) -0.003(2) C42 0.039(3) 0.036(3) 0.035(3) -0.004(2) 0.003(2) 0.001(2) C43 0.053(4) 0.047(3) 0.043(3) 0.007(3) 0.000(3) -0.018(3) C44 0.062(4) 0.037(3) 0.034(3) -0.007(2) -0.002(3) -0.013(3) N45 0.029(2) 0.038(3) 0.072(3) 0.011(2) -0.001(2) 0.000(2) C46 0.048(3) 0.041(3) 0.033(3) 0.001(2) -0.004(2) -0.001(3) C47 0.050(3) 0.033(3) 0.040(3) 0.002(2) 0.001(2) -0.010(2) C48 0.045(3) 0.036(3) 0.036(3) 0.000(2) -0.002(2) 0.013(2) C49 0.039(3) 0.045(3) 0.034(3) -0.002(2) -0.005(2) -0.002(2) C50 0.055(4) 0.044(3) 0.048(3) 0.011(3) -0.008(3) -0.003(3) C51 0.046(3) 0.046(3) 0.039(3) 0.001(2) -0.009(2) -0.022(3) C52 0.050(4) 0.065(4) 0.034(3) -0.001(3) -0.002(3) -0.002(3) C53 0.077(5) 0.088(5) 0.038(3) 0.003(3) -0.014(3) 0.000(4) C54 0.061(4) 0.077(5) 0.049(4) -0.005(3) -0.010(3) -0.014(4)