#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/04/4000419.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_4000419
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/cm049594l
_journal_year                    2004
_chemical_formula_sum            'C18 H33 N3 O3 S'
_chemical_formula_weight         371.72
_chemical_name_common            'undecylbenzene sulfonate'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                82.830(5)
_cell_angle_beta                 86.091(5)
_cell_angle_gamma                89.365(5)
_cell_formula_units_Z            4
_cell_length_a                   7.796(2)
_cell_length_b                   11.825(4)
_cell_length_c                   23.588(7)
_cell_measurement_reflns_used    1651
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_cell_volume                     2152.6(11)
_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  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0670
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20775
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         0.87
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.709990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             808
_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   0.996
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         7558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1024P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1656
_refine_ls_wR_factor_ref         0.1821
_reflns_number_gt                4506
_reflns_number_total             7558
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C18 H33 N3 O3 S1'
_cod_database_code               4000419
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.05950(8) 0.75272(6) 0.09269(3) 0.0375(2) Uani 1 1 d . . .
O6 O 0.5600(2) 0.68112(17) -0.08697(8) 0.0433(5) Uani 1 1 d . . .
N4 N 0.4269(3) 0.2656(2) -0.05824(9) 0.0437(6) Uani 1 1 d . . .
H4A H 0.3295 0.2282 -0.0572 0.052 Uiso 1 1 calc R . .
H4B H 0.5254 0.2286 -0.0594 0.052 Uiso 1 1 calc R . .
C36 C 0.4847(5) 1.6890(3) -0.77310(14) 0.0753(11) Uani 1 1 d . . .
H36A H 0.4827 1.7715 -0.7848 0.113 Uiso 1 1 calc R . .
H36B H 0.3937 1.6528 -0.7911 0.113 Uiso 1 1 calc R . .
H36C H 0.5966 1.6581 -0.7852 0.113 Uiso 1 1 calc R . .
S2 S 0.40208(8) 0.74718(6) -0.09155(3) 0.0383(2) Uani 1 1 d . . .
O5 O 0.2491(2) 0.67780(17) -0.07624(8) 0.0433(5) Uani 1 1 d . . .
N1 N 0.2467(3) 1.0618(2) 0.06167(11) 0.0499(7) Uani 1 1 d . . .
H1A H 0.3460 1.0961 0.0623 0.060 Uiso 1 1 calc R . .
H1B H 0.2430 0.9873 0.0622 0.060 Uiso 1 1 calc R . .
C1 C -0.1175(4) -0.1896(3) 0.77451(14) 0.0728(11) Uani 1 1 d . . .
H1C H -0.1226 -0.2721 0.7861 0.109 Uiso 1 1 calc R . .
H1D H -0.2168 -0.1530 0.7925 0.109 Uiso 1 1 calc R . .
H1E H -0.0113 -0.1594 0.7867 0.109 Uiso 1 1 calc R . .
O3 O -0.0874(2) 0.82474(16) 0.07791(7) 0.0408(5) Uani 1 1 d . . .
N3 N 0.2773(3) 0.4331(2) -0.05638(10) 0.0482(7) Uani 1 1 d . . .
H3B H 0.1797 0.3960 -0.0553 0.058 Uiso 1 1 calc R . .
H3C H 0.2767 0.5075 -0.0563 0.058 Uiso 1 1 calc R . .
C2 C -0.1203(4) -0.1652(3) 0.70947(13) 0.0575(9) Uani 1 1 d . . .
H2A H -0.0211 -0.2040 0.6917 0.069 Uiso 1 1 calc R . .
H2B H -0.2264 -0.1979 0.6975 0.069 Uiso 1 1 calc R . .
O2 O 0.2190(2) 0.81681(17) 0.08806(8) 0.0447(5) Uani 1 1 d . . .
N2 N 0.1067(3) 1.2342(2) 0.05906(10) 0.0435(6) Uani 1 1 d . . .
H2D H 0.0105 1.2738 0.0580 0.052 Uiso 1 1 calc R . .
H2E H 0.2056 1.2690 0.0595 0.052 Uiso 1 1 calc R . .
C35 C 0.4553(4) 1.6650(3) -0.70807(13) 0.0584(9) Uani 1 1 d . . .
H35A H 0.5462 1.7034 -0.6902 0.070 Uiso 1 1 calc R . .
H35B H 0.3434 1.6982 -0.6962 0.070 Uiso 1 1 calc R . .
O4 O 0.4033(2) 0.84771(16) -0.06149(7) 0.0409(5) Uani 1 1 d . . .
N5 N -0.0456(3) 1.0684(2) 0.05917(9) 0.0433(6) Uani 1 1 d . . .
H5B H -0.1426 1.1071 0.0582 0.052 Uiso 1 1 calc R . .
H5C H -0.0467 0.9939 0.0597 0.052 Uiso 1 1 calc R . .
C14 C -0.0162(4) 0.5456(3) 0.24199(12) 0.0482(8) Uani 1 1 d . . .
H14A H -0.0202 0.4659 0.2540 0.058 Uiso 1 1 calc R . .
O1 O 0.0733(2) 0.65292(16) 0.06228(8) 0.0404(5) Uiso 1 1 d . . .
N6 N 0.5710(3) 0.4343(2) -0.05983(10) 0.0450(6) Uani 1 1 d . . .
H6B H 0.6700 0.3980 -0.0611 0.054 Uiso 1 1 calc R . .
H6C H 0.5688 0.5087 -0.0597 0.054 Uiso 1 1 calc R . .
C33 C 0.4292(4) 1.5119(3) -0.62111(11) 0.0466(8) Uani 1 1 d . . .
H33A H 0.5204 1.5497 -0.6032 0.056 Uiso 1 1 calc R . .
H33B H 0.3175 1.5444 -0.6084 0.056 Uiso 1 1 calc R . .
C13 C -0.0310(4) 0.7366(3) 0.26349(12) 0.0494(8) Uani 1 1 d . . .
H13A H -0.0452 0.7893 0.2907 0.059 Uiso 1 1 calc R . .
C24 C 0.3835(4) 0.7630(3) -0.26225(12) 0.0489(8) Uani 1 1 d . . .
H24A H 0.3802 0.7098 -0.2892 0.059 Uiso 1 1 calc R . .
C3 C -0.1133(4) -0.0398(3) 0.68712(11) 0.0474(8) Uani 1 1 d . . .
H3D H -0.0082 -0.0072 0.6999 0.057 Uiso 1 1 calc R . .
H3E H -0.2133 -0.0015 0.7047 0.057 Uiso 1 1 calc R . .
C34 C 0.4562(4) 1.5399(3) -0.68617(11) 0.0477(8) Uani 1 1 d . . .
H34A H 0.5676 1.5070 -0.6988 0.057 Uiso 1 1 calc R . .
H34B H 0.3647 1.5021 -0.7040 0.057 Uiso 1 1 calc R . .
C15 C -0.0031(4) 0.7781(3) 0.20566(12) 0.0490(8) Uani 1 1 d . . .
H15A H -0.0006 0.8577 0.1936 0.059 Uiso 1 1 calc R . .
C4 C -0.1132(4) -0.0120(3) 0.62189(12) 0.0450(7) Uani 1 1 d . . .
H4D H -0.0128 -0.0498 0.6042 0.054 Uiso 1 1 calc R . .
H4E H -0.2180 -0.0447 0.6090 0.054 Uiso 1 1 calc R . .
C22 C 0.3899(4) 0.7225(3) -0.20476(12) 0.0488(8) Uani 1 1 d . . .
H22A H 0.3924 0.6428 -0.1927 0.059 Uiso 1 1 calc R . .
C16 C 0.0122(4) 0.5852(3) 0.18399(11) 0.0453(7) Uani 1 1 d . . .
H16A H 0.0255 0.5324 0.1567 0.054 Uiso 1 1 calc R . .
C32 C 0.4309(4) 1.3862(3) -0.59960(11) 0.0428(7) Uani 1 1 d . . .
H32A H 0.5410 1.3533 -0.6134 0.051 Uiso 1 1 calc R . .
H32B H 0.3373 1.3489 -0.6167 0.051 Uiso 1 1 calc R . .
C29 C 0.3961(4) 1.2007(3) -0.44885(11) 0.0420(7) Uani 1 1 d . . .
H29A H 0.4950 1.2344 -0.4329 0.050 Uiso 1 1 calc R . .
H29B H 0.2900 1.2356 -0.4331 0.050 Uiso 1 1 calc R . .
C23 C 0.3831(4) 0.9536(3) -0.24132(12) 0.0469(8) Uani 1 1 d . . .
H23A H 0.3802 1.0333 -0.2534 0.056 Uiso 1 1 calc R . .
C9 C -0.0845(4) 0.4247(3) 0.42963(11) 0.0426(7) Uani 1 1 d . . .
H9A H 0.0093 0.4608 0.4472 0.051 Uiso 1 1 calc R . .
H9B H -0.1945 0.4572 0.4437 0.051 Uiso 1 1 calc R . .
C11 C -0.0667(4) 0.5818(3) 0.34610(11) 0.0461(8) Uani 1 1 d . . .
H11A H 0.0224 0.6176 0.3659 0.055 Uiso 1 1 calc R . .
H11B H -0.1795 0.6113 0.3597 0.055 Uiso 1 1 calc R . .
C7 C -0.0980(4) 0.2681(3) 0.51470(11) 0.0421(7) Uani 1 1 d . . .
H7A H 0.0004 0.3024 0.5307 0.050 Uiso 1 1 calc R . .
H7B H -0.2044 0.3031 0.5301 0.050 Uiso 1 1 calc R . .
C21 C 0.3888(4) 0.9141(3) -0.18315(11) 0.0450(7) Uani 1 1 d . . .
H21A H 0.3901 0.9670 -0.1560 0.054 Uiso 1 1 calc R . .
C30 C 0.4098(3) 1.2308(2) -0.51406(11) 0.0411(7) Uani 1 1 d . . .
H30A H 0.5172 1.1973 -0.5296 0.049 Uiso 1 1 calc R . .
H30B H 0.3124 1.1952 -0.5300 0.049 Uiso 1 1 calc R . .
C20 C 0.3926(3) 0.7989(2) -0.16496(11) 0.0369(7) Uani 1 1 d . . .
C19 C 0.4251(3) 0.3770(3) -0.05809(11) 0.0376(7) Uani 1 1 d . . .
C27 C 0.3869(3) 1.0437(3) -0.36408(11) 0.0428(7) Uani 1 1 d . . .
H27A H 0.4901 1.0753 -0.3496 0.051 Uiso 1 1 calc R . .
H27B H 0.2846 1.0800 -0.3467 0.051 Uiso 1 1 calc R . .
C26 C 0.3800(4) 0.9175(3) -0.34567(11) 0.0441(7) Uani 1 1 d . . .
H26A H 0.4792 0.8820 -0.3652 0.053 Uiso 1 1 calc R . .
H26B H 0.2745 0.8877 -0.3595 0.053 Uiso 1 1 calc R . .
C8 C -0.0835(4) 0.2983(3) 0.44957(11) 0.0424(7) Uani 1 1 d . . .
H8A H 0.0243 0.2651 0.4341 0.051 Uiso 1 1 calc R . .
H8B H -0.1804 0.2626 0.4334 0.051 Uiso 1 1 calc R . .
C31 C 0.4093(4) 1.3571(3) -0.53436(11) 0.0449(8) Uani 1 1 d . . .
H31A H 0.5036 1.3933 -0.5171 0.054 Uiso 1 1 calc R . .
H31B H 0.2996 1.3902 -0.5203 0.054 Uiso 1 1 calc R . .
C18 C 0.1024(3) 1.1224(3) 0.05986(11) 0.0390(7) Uani 1 1 d . . .
C28 C 0.3924(4) 1.0739(2) -0.42917(11) 0.0416(7) Uani 1 1 d . . .
H28A H 0.4958 1.0384 -0.4464 0.050 Uiso 1 1 calc R . .
H28B H 0.2904 1.0407 -0.4436 0.050 Uiso 1 1 calc R . .
C17 C 0.0211(3) 0.7005(2) 0.16598(11) 0.0347(7) Uani 1 1 d . . .
C10 C -0.0626(4) 0.4553(3) 0.36473(11) 0.0417(7) Uani 1 1 d . . .
H10A H 0.0483 0.4242 0.3505 0.050 Uiso 1 1 calc R . .
H10B H -0.1555 0.4187 0.3470 0.050 Uiso 1 1 calc R . .
C5 C -0.1068(4) 0.1132(3) 0.60020(11) 0.0433(7) Uani 1 1 d . . .
H5D H -0.0039 0.1462 0.6142 0.052 Uiso 1 1 calc R . .
H5E H -0.2090 0.1505 0.6171 0.052 Uiso 1 1 calc R . .
C6 C -0.1014(4) 0.1422(3) 0.53520(11) 0.0427(7) Uani 1 1 d . . .
H6D H 0.0021 0.1064 0.5182 0.051 Uiso 1 1 calc R . .
H6E H -0.2033 0.1085 0.5210 0.051 Uiso 1 1 calc R . .
C12 C -0.0388(3) 0.6215(3) 0.28246(11) 0.0399(7) Uani 1 1 d . . .
C25 C 0.3816(3) 0.8778(3) -0.28170(11) 0.0389(7) Uani 1 1 d . . .
