#------------------------------------------------------------------------------
#$Date: 2016-03-21 01:21:50 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178377 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/04/4000424.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_4000424
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/cm049594l
_journal_year                    2004
_chemical_formula_sum            'C23 H35 N3 O3 S'
_chemical_formula_weight         433.60
_chemical_name_common            'guanidinium decylbiphenylsulfonate'
_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                 92.893(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6689(16)
_cell_length_b                   7.9238(16)
_cell_length_c                   38.321(8)
_cell_measurement_reflns_used    880
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      50.745
_cell_measurement_theta_min      5.565
_cell_volume                     2325.7(8)
_diffrn_ambient_temperature      293(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  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0734
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            16342
_diffrn_reflns_theta_max         28.01
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.469904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5445
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.1541
_refine_ls_R_factor_gt           0.1114
_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)+(0.0453P)²+9.5781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2236
_refine_ls_wR_factor_ref         0.2405
_reflns_number_gt                3754
_reflns_number_total             5445
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4000424
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 0.75922(14) 0.69870(16) 0.30638(3) 0.0278(3) Uani 1 1 d . . .
O1 O 0.9178(4) 0.7985(5) 0.31267(8) 0.0356(8) Uani 1 1 d . . .
O2 O 0.7562(4) 0.6108(5) 0.27273(8) 0.0334(8) Uani 1 1 d . . .
O3 O 0.6037(4) 0.8021(5) 0.31062(8) 0.0365(8) Uani 1 1 d . . .
N1 N 0.9050(5) 0.0767(5) 0.25965(10) 0.0331(9) Uani 1 1 d . . .
H1A H 1.0007 0.1072 0.2507 0.040 Uiso 1 1 calc R . .
H1B H 0.9078 0.0141 0.2780 0.040 Uiso 1 1 calc R . .
N2 N 0.6053(5) 0.0819(6) 0.25939(10) 0.0353(10) Uani 1 1 d . . .
H2A H 0.5064 0.1156 0.2504 0.042 Uiso 1 1 calc R . .
H2B H 0.6090 0.0192 0.2777 0.042 Uiso 1 1 calc R . .
N3 N 0.7476(5) 0.2228(5) 0.21678(10) 0.0328(9) Uani 1 1 d . . .
H3A H 0.6490 0.2568 0.2076 0.039 Uiso 1 1 calc R . .
H3B H 0.8432 0.2513 0.2076 0.039 Uiso 1 1 calc R . .
C1 C 0.7606(6) 0.2957(6) 0.39171(11) 0.0302(10) Uani 1 1 d . . .
C2 C 0.7521(6) 0.1265(6) 0.24501(11) 0.0271(10) Uani 1 1 d . . .
C3 C 0.7586(6) 0.5410(6) 0.33920(11) 0.0273(10) Uani 1 1 d . . .
C4 C 0.7430(7) 0.4676(6) 0.39945(12) 0.0357(11) Uani 1 1 d . . .
H4 H 0.7320 0.5007 0.4225 0.043 Uiso 1 1 calc R . .
C5 C 0.7765(7) 0.2515(7) 0.35682(12) 0.0383(12) Uani 1 1 d . . .
H5 H 0.7877 0.1384 0.3508 0.046 Uiso 1 1 calc R . .
C6 C 0.7416(6) 0.5888(6) 0.37354(12) 0.0345(11) Uani 1 1 d . . .
H6 H 0.7292 0.7022 0.3792 0.041 Uiso 1 1 calc R . .
C7 C 0.7617(6) 0.1679(6) 0.42017(12) 0.0296(10) Uani 1 1 d . . .
C8 C 0.6803(7) 0.2001(7) 0.45143(12) 0.0380(11) Uani 1 1 d . . .
H8 H 0.6182 0.3000 0.4538 0.046 Uiso 1 1 calc R . .
C9 C 0.7760(7) 0.3736(7) 0.33094(12) 0.0368(12) Uani 1 1 d . . .
H9 H 0.7875 0.3418 0.3078 0.044 Uiso 1 1 calc R . .
C10 C 0.7673(11) -0.3537(9) 0.50585(18) 0.083(3) Uani 1 1 d . . .
H10A H 0.8439 -0.4081 0.4899 0.099 Uiso 1 1 calc R . .
H10B H 0.6478 -0.3676 0.4968 0.099 Uiso 1 1 calc R . .
C11 C 0.8456(7) 0.0136(6) 0.41780(13) 0.0364(11) Uani 1 1 d . . .
H11 H 0.8966 -0.0146 0.3971 0.044 Uiso 1 1 calc R . .
C12 C 0.7905(13) -0.4357(12) 0.5425(2) 0.130(5) Uani 1 1 d D . .
H12A H 0.9147 -0.4534 0.5471 0.156 Uiso 1 1 calc R . .
H12B H 0.7546 -0.3524 0.5593 0.156 Uiso 1 1 calc R . .
C13 C 0.7811(7) -0.0631(7) 0.47696(13) 0.0390(12) Uani 1 1 d . . .
C14 C 0.8559(7) -0.0995(7) 0.44529(13) 0.0412(12) Uani 1 1 d . . .
H14 H 0.9135 -0.2017 0.4427 0.049 Uiso 1 1 calc R . .
C15 C 0.7182(7) -0.8963(8) 0.62566(13) 0.0500(15) Uani 1 1 d . . .
H15A H 0.6325 -0.8449 0.6401 0.060 Uiso 1 1 calc R . .
H15B H 0.8327 -0.8607 0.6348 0.060 Uiso 1 1 calc R . .
C16 C 0.8101(8) -0.1725(8) 0.50873(15) 0.0536(16) Uani 1 1 d . . .
H16A H 0.9322 -0.1633 0.5164 0.064 Uiso 1 1 calc R . .
H16B H 0.7424 -0.1255 0.5271 0.064 Uiso 1 1 calc R . .
C17 C 0.6906(7) 0.0862(7) 0.47883(13) 0.0419(13) Uani 1 1 d . . .
H17 H 0.6345 0.1114 0.4991 0.050 Uiso 1 1 calc R . .
C18 C 0.7294(10) -1.3365(9) 0.6720(3) 0.105(4) Uani 1 1 d . . .
H18A H 0.6139 -1.3786 0.6665 0.158 Uiso 1 1 calc R . .
H18B H 0.7629 -1.3623 0.6959 0.158 Uiso 1 1 calc R . .
H18C H 0.8098 -1.3886 0.6569 0.158 Uiso 1 1 calc R . .
C19 C 0.7057(7) -1.0881(9) 0.62947(18) 0.0610(19) Uani 1 1 d . . .
H19A H 0.5918 -1.1254 0.6204 0.073 Uiso 1 1 calc R . .
H19B H 0.7931 -1.1409 0.6157 0.073 Uiso 1 1 calc R . .
C20 C 0.7320(9) -1.1440(8) 0.6667(2) 0.0668(19) Uani 1 1 d . . .
H20A H 0.6413 -1.0941 0.6801 0.080 Uiso 1 1 calc R . .
H20B H 0.8432 -1.1006 0.6760 0.080 Uiso 1 1 calc R . .
C21 C 0.6906(8) -0.8287(12) 0.58911(15) 0.073(2) Uani 1 1 d . . .
H21A H 0.7648 -0.8899 0.5737 0.088 Uiso 1 1 calc R . .
H21B H 0.5703 -0.8477 0.5811 0.088 Uiso 1 1 calc R . .
C22 C 0.7305(9) -0.6441(13) 0.58701(17) 0.088(3) Uani 1 1 d . . .
H22A H 0.8487 -0.6244 0.5963 0.106 Uiso 1 1 calc R . .
H22B H 0.6519 -0.5824 0.6014 0.106 Uiso 1 1 calc R . .
C23 C 0.7124(10) -0.5776(16) 0.5500(2) 0.137(5) Uani 1 1 d D . .
H23A H 0.7551 -0.6641 0.5347 0.164 Uiso 1 1 calc R . .
H23B H 0.5888 -0.5637 0.5440 0.164 Uiso 1 1 calc R . .
