#------------------------------------------------------------------------------
#$Date: 2016-03-21 01:21:50 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178377 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/04/4000421.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_4000421
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/cm049594l
_journal_year                    2004
_chemical_formula_sum            'C21 H39 N3 O3 S'
_chemical_formula_weight         413.61
_chemical_name_common            'guanidinium tetradecylbenzenesulfonate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 92.131(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.8868(8)
_cell_length_b                   10.1325(10)
_cell_length_c                   59.017(6)
_cell_measurement_reflns_used    3307
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      51.417
_cell_measurement_theta_min      4.523
_cell_volume                     4713.0(8)
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device_type  'Siemens SMART Platform CCD'
_diffrn_measurement_method       'area detector, omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_sigmaI/netI    0.1075
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -75
_diffrn_reflns_number            28804
_diffrn_reflns_theta_max         27.12
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.712407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         10302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.1553
_refine_ls_R_factor_gt           0.0973
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0614P)²+9.7073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2173
_refine_ls_wR_factor_ref         0.2372
_reflns_number_gt                6158
_reflns_number_total             10302
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4000421
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'
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_symmetry_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 . .
