#------------------------------------------------------------------------------
#$Date: 2016-03-21 01:21:50 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178377 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/04/4000423.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_4000423
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/cm049594l
_journal_year                    2004
_chemical_formula_sum            'C21 H31 N3 O3 S'
_chemical_formula_weight         405.55
_chemical_name_common            'guanidinium octylbiphenylsulfonate'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6188(13)
_cell_length_b                   7.7097(13)
_cell_length_c                   36.330(6)
_cell_measurement_reflns_used    3269
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_cell_volume                     2134.0(6)
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device_type  'Bruker 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  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            21010
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.784236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0364P)²+0.7297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0840
_reflns_number_gt                3466
_reflns_number_total             3773
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4000423
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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 0.25324(7) 0.83037(6) 0.811165(12) 0.02736(12) Uani 1 1 d . . .
O1 O 0.41029(19) 0.9364(2) 0.81523(4) 0.0335(4) Uani 1 1 d . . .
O2 O 0.09552(19) 0.9332(2) 0.81772(4) 0.0331(4) Uani 1 1 d . . .
N3 N 0.2457(3) 1.36041(19) 0.71454(4) 0.0329(4) Uani 1 1 d . . .
H3A H 0.1451 1.3921 0.7047 0.039 Uiso 1 1 calc R . .
H3B H 0.3451 1.3926 0.7043 0.039 Uiso 1 1 calc R . .
C4 C 0.2638(3) 0.6697(2) 0.84611(5) 0.0267(4) Uani 1 1 d . . .
O5 O 0.2478(2) 0.73856(17) 0.77608(3) 0.0342(3) Uani 1 1 d . . .
N6 N 0.3996(2) 1.2200(3) 0.76002(5) 0.0343(5) Uani 1 1 d . . .
H6A H 0.4991 1.2543 0.7501 0.041 Uiso 1 1 calc R . .
H6B H 0.4005 1.1561 0.7801 0.041 Uiso 1 1 calc R . .
N7 N 0.0985(2) 1.2156(3) 0.76028(5) 0.0337(5) Uani 1 1 d . . .
H7A H -0.0025 1.2469 0.7506 0.040 Uiso 1 1 calc R . .
H7B H 0.1006 1.1517 0.7804 0.040 Uiso 1 1 calc R . .
C8 C 0.2476(3) 1.2646(2) 0.74464(5) 0.0282(4) Uani 1 1 d . . .
C9 C 0.2485(3) 0.3738(2) 0.86605(5) 0.0329(4) Uani 1 1 d . . .
H9 H 0.2300 0.2548 0.8604 0.039 Uiso 1 1 calc R . .
C10 C 0.2413(3) 0.0185(2) 0.96212(5) 0.0288(4) Uani 1 1 d . . .
H10 H 0.1806 -0.0891 0.9617 0.035 Uiso 1 1 calc R . .
C11 C 0.2434(4) -0.4812(3) 1.07426(5) 0.0368(5) Uani 1 1 d . . .
H11A H 0.3176 -0.5570 1.0587 0.044 Uiso 1 1 calc R . .
H11B H 0.1200 -0.4963 1.0664 0.044 Uiso 1 1 calc R . .
C12 C 0.2452(4) -0.7308(3) 1.12064(5) 0.0384(5) Uani 1 1 d . . .
H12A H 0.1317 -0.7715 1.1105 0.046 Uiso 1 1 calc R . .
H12B H 0.3401 -0.7908 1.1070 0.046 Uiso 1 1 calc R . .
C13 C 0.2356(3) 0.4966(3) 0.83816(5) 0.0335(4) Uani 1 1 d . . .
H13 H 0.2075 0.4618 0.8138 0.040 Uiso 1 1 calc R . .
C14 C 0.3694(3) -0.0499(3) 1.02630(6) 0.0365(5) Uani 1 1 d . . .
H14A H 0.3276 0.0209 1.0473 0.044 Uiso 1 1 calc R . .
H14B H 0.4967 -0.0685 1.0300 0.044 Uiso 1 1 calc R . .
C15 C 0.2612(4) -0.5368(3) 1.11425(5) 0.0350(4) Uani 1 1 d . . .
H15A H 0.3767 -0.4977 1.1235 0.042 Uiso 1 1 calc R . .
H15B H 0.1696 -0.4771 1.1289 0.042 Uiso 1 1 calc R . .
C16 C 0.2444(5) -0.9733(3) 1.16794(8) 0.0644(7) Uani 1 1 d . . .
H16A H 0.1320 -1.0174 1.1588 0.097 Uiso 1 1 calc R . .
H16B H 0.2532 -0.9950 1.1945 0.097 Uiso 1 1 calc R . .
H16C H 0.3408 -1.0323 1.1552 0.097 Uiso 1 1 calc R . .
C17 C 0.2557(4) -0.7803(3) 1.16080(6) 0.0472(5) Uani 1 1 d . . .
H17A H 0.1592 -0.7219 1.1742 0.057 Uiso 1 1 calc R . .
H17B H 0.3679 -0.7365 1.1710 0.057 Uiso 1 1 calc R . .
C18 C 0.2216(3) 0.1342(2) 0.93259(5) 0.0288(4) Uani 1 1 d . . .
H18 H 0.1477 0.1037 0.9126 0.035 Uiso 1 1 calc R . .
C19 C 0.2882(2) 0.4217(3) 0.90220(5) 0.0261(4) Uani 1 1 d . . .
C20 C 0.3120(3) 0.5989(3) 0.90918(6) 0.0340(5) Uani 1 1 d . . .
H20 H 0.3359 0.6355 0.9336 0.041 Uiso 1 1 calc R . .
C21 C 0.4377(3) 0.2153(3) 0.99067(6) 0.0339(5) Uani 1 1 d . . .
H21 H 0.5137 0.2448 1.0104 0.041 Uiso 1 1 calc R . .
C22 C 0.3480(3) 0.0583(3) 0.99190(5) 0.0292(5) Uani 1 1 d . . .
C23 C 0.2809(3) -0.2255(3) 1.02913(5) 0.0337(5) Uani 1 1 d . . .
H23A H 0.3367 -0.3077 1.0118 0.040 Uiso 1 1 calc R . .
H23B H 0.1554 -0.2147 1.0224 0.040 Uiso 1 1 calc R . .
C24 C 0.2971(3) -0.2945(3) 1.06840(6) 0.0357(5) Uani 1 1 d . . .
H24A H 0.4207 -0.2814 1.0763 0.043 Uiso 1 1 calc R . .
H24B H 0.2246 -0.2206 1.0847 0.043 Uiso 1 1 calc R . .
C27 C 0.3017(3) 0.7217(3) 0.88169(5) 0.0328(5) Uani 1 1 d . . .
H27 H 0.3204 0.8408 0.8871 0.039 Uiso 1 1 calc R . .
C28 C 0.4202(3) 0.3290(3) 0.96184(5) 0.0327(5) Uani 1 1 d . . .
H28 H 0.4849 0.4343 0.9620 0.039 Uiso 1 1 calc R . .
C34 C 0.3086(2) 0.2928(3) 0.93217(5) 0.0264(4) Uani 1 1 d . . .
