 
data_06skc0070p212121
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Toluidinium aniline-4-sulphonate
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H16 N2 O3 S'
_chemical_formula_weight          280.34
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            orthorhombic
_symmetry_space_group_name_H-M    P212121
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    7.0493(4)
_cell_length_b                    11.3995(5)
_cell_length_c                    16.4313(9)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1320.39(12)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3003
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.18
_exptl_crystal_size_mid           0.17
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.410
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              592
_exptl_absorpt_coefficient_mu     0.251
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9562
_exptl_absorpt_correction_T_max   0.9975
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)' 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             13243
_diffrn_reflns_av_R_equivalents   0.0957
_diffrn_reflns_av_sigmaI/netI     0.0905
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          3.14
_diffrn_reflns_theta_max          27.47
_reflns_number_total              3016
_reflns_number_gt                 2349
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'  
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 Checkcif brings up alerts regarding possible additional pseudosymmetry due
 to the approximate 2-fold rotation axes present in the molecules; further
 investigation using ADDSYM in PLATON did not show any missed symmetry.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0351P)²+5.3327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.2(2)
_refine_ls_number_reflns          3016
_refine_ls_number_parameters      174
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1076
_refine_ls_R_factor_gt            0.0809
_refine_ls_wR_factor_ref          0.1764
_refine_ls_wR_factor_gt           0.1607
_refine_ls_goodness_of_fit_ref    1.057
_refine_ls_restrained_S_all       1.057
_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_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.2381(7) 0.8871(4) 0.4096(3) 0.0118(9) Uani 1 1 d . . .
C2 C 0.2975(8) 0.9705(4) 0.4651(3) 0.0193(11) Uani 1 1 d . . .
H2 H 0.3562 1.0407 0.4468 0.023 Uiso 1 1 calc R . .
C3 C 0.2707(8) 0.9511(4) 0.5479(3) 0.0182(11) Uani 1 1 d . . .
H3 H 0.3118 1.0084 0.5860 0.022 Uiso 1 1 calc R . .
C4 C 0.1846(7) 0.8490(5) 0.5757(3) 0.0168(11) Uani 1 1 d . . .
C5 C 0.1265(8) 0.7652(4) 0.5183(3) 0.0182(11) Uani 1 1 d . . .
H5 H 0.0693 0.6943 0.5361 0.022 Uiso 1 1 calc R . .
C6 C 0.1516(7) 0.7848(4) 0.4367(3) 0.0170(11) Uani 1 1 d . . .
H6 H 0.1096 0.7280 0.3984 0.020 Uiso 1 1 calc R . .
N4 N 0.1523(8) 0.8298(4) 0.6569(3) 0.0290(12) Uani 1 1 d . . .
H4A H 0.1863 0.8829 0.6929 0.035 Uiso 1 1 calc R . .
H4B H 0.0975 0.7644 0.6730 0.035 Uiso 1 1 calc R . .
O1A O 0.4719(5) 0.9294(3) 0.2913(2) 0.0253(9) Uani 1 1 d . . .
O1B O 0.2025(6) 0.8044(3) 0.2643(2) 0.0258(9) Uani 1 1 d . . .
O1C O 0.1556(6) 1.0124(3) 0.2821(2) 0.0259(9) Uani 1 1 d . . .
S1 S 0.26853(17) 0.90968(10) 0.30432(7) 0.0159(3) Uani 1 1 d . . .
C21 C 0.2504(8) 0.6077(4) 0.1069(3) 0.0181(10) Uani 1 1 d . . .
C22 C 0.1943(8) 0.5222(4) 0.0519(3) 0.0201(12) Uani 1 1 d . . .
H22 H 0.1417 0.4504 0.0706 0.024 Uiso 1 1 calc R . .
C23 C 0.2155(8) 0.5425(4) -0.0305(3) 0.0209(11) Uani 1 1 d . . .
H23 H 0.1793 0.4836 -0.0683 0.025 Uiso 1 1 calc R . .
C24 C 0.2895(7) 0.6485(5) -0.0590(3) 0.0178(11) Uani 1 1 d . . .
C25 C 0.3475(8) 0.7310(5) -0.0019(3) 0.0203(12) Uani 1 1 d . . .
H25 H 0.4027 0.8024 -0.0200 0.024 Uiso 1 1 calc R . .
C26 C 0.3267(7) 0.7117(4) 0.0807(3) 0.0168(11) Uani 1 1 d . . .
H26 H 0.3647 0.7697 0.1189 0.020 Uiso 1 1 calc R . .
C27 C 0.3113(9) 0.6732(6) -0.1488(3) 0.0309(15) Uani 1 1 d . . .
H27A H 0.3129 0.7582 -0.1578 0.046 Uiso 1 1 calc R . .
H27B H 0.2046 0.6385 -0.1785 0.046 Uiso 1 1 calc R . .
H27C H 0.4304 0.6391 -0.1684 0.046 Uiso 1 1 calc R . .
N21 N 0.2269(6) 0.5835(4) 0.1949(2) 0.0211(9) Uani 1 1 d . . .
H21A H 0.3257 0.5390 0.2128 0.032 Uiso 1 1 calc R . .
H21B H 0.1162 0.5441 0.2031 0.032 Uiso 1 1 calc R . .
H21C H 0.2242 0.6524 0.2228 0.032 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
C1 0.014(2) 0.009(2) 0.013(2) 0.0006(16) 0.001(2) -0.002(2)
C2 0.021(3) 0.010(2) 0.027(3) -0.002(2) 0.002(2) 0.000(2)
C3 0.018(3) 0.017(2) 0.020(2) -0.0103(18) 0.003(2) -0.004(2)
C4 0.013(3) 0.021(3) 0.017(2) 0.004(2) 0.004(2) 0.002(2)
C5 0.011(2) 0.013(2) 0.030(3) 0.003(2) 0.004(2) -0.004(2)
C6 0.014(3) 0.014(2) 0.022(3) -0.003(2) 0.000(2) -0.004(2)
N4 0.043(3) 0.028(3) 0.017(2) -0.0021(19) 0.004(2) -0.014(2)
O1A 0.0163(18) 0.031(2) 0.029(2) -0.0046(17) 0.0031(16) -0.0001(16)
O1B 0.031(2) 0.0219(18) 0.0245(19) -0.0011(15) -0.0038(17) -0.0050(17)
O1C 0.029(2) 0.026(2) 0.023(2) 0.0052(16) 0.0065(17) 0.0086(17)
S1 0.0139(6) 0.0178(5) 0.0159(5) -0.0017(5) 0.0003(5) 0.0022(5)
C21 0.013(2) 0.020(2) 0.021(2) 0.0006(18) 0.003(2) -0.001(2)
C22 0.017(3) 0.009(2) 0.034(3) 0.002(2) 0.006(2) -0.0015(19)
C23 0.017(3) 0.017(2) 0.029(3) -0.006(2) 0.003(2) 0.001(2)
C24 0.009(2) 0.028(3) 0.017(2) -0.001(2) 0.003(2) 0.006(2)
C25 0.020(3) 0.014(3) 0.026(3) 0.004(2) 0.003(2) 0.004(2)
C26 0.009(2) 0.011(2) 0.031(3) -0.004(2) 0.006(2) 0.0020(19)
C27 0.030(4) 0.035(3) 0.027(3) 0.006(2) 0.000(3) -0.009(3)
N21 0.023(2) 0.0178(19) 0.0229(19) 0.0037(19) 0.003(2) -0.002(2)
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C2 1.382(7) . ?
C1 C6 1.389(6) . ?
C1 S1 1.763(4) . ?
C2 C3 1.392(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(7) . ?
C3 H3 0.9500 . ?
C4 N4 1.371(6) . ?
C4 C5 1.404(7) . ?
C5 C6 1.371(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
O1A S1 1.467(4) . ?
O1B S1 1.445(4) . ?
O1C S1 1.462(4) . ?
C21 C26 1.371(7) . ?
C21 C22 1.386(7) . ?
C21 N21 1.482(6) . ?
C22 C23 1.381(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.396(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(7) . ?
C24 C27 1.510(7) . ?
C25 C26 1.383(7) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
N21 H21A 0.9100 . ?
N21 H21B 0.9100 . ?
N21 H21C 0.9100 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 C1 C6 120.0(4) . . ?
C2 C1 S1 120.6(3) . . ?
C6 C1 S1 119.4(3) . . ?
C1 C2 C3 119.6(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.9(5) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
N4 C4 C3 121.7(5) . . ?
N4 C4 C5 119.8(5) . . ?
C3 C4 C5 118.4(4) . . ?
C6 C5 C4 120.6(5) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.4(5) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C4 N4 H4A 120.0 . . ?
C4 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
O1B S1 O1C 112.1(2) . . ?
O1B S1 O1A 112.1(2) . . ?
O1C S1 O1A 111.9(2) . . ?
O1B S1 C1 106.6(2) . . ?
O1C S1 C1 107.2(2) . . ?
O1A S1 C1 106.6(2) . . ?
C26 C21 C22 121.0(5) . . ?
C26 C21 N21 120.7(4) . . ?
C22 C21 N21 118.3(4) . . ?
C23 C22 C21 119.4(5) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 120.9(5) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 118.0(5) . . ?
C25 C24 C27 120.2(5) . . ?
C23 C24 C27 121.8(5) . . ?
C26 C25 C24 121.5(5) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C21 C26 C25 119.1(5) . . ?
C21 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C21 N21 H21A 109.5 . . ?
C21 N21 H21B 109.5 . . ?
H21A N21 H21B 109.5 . . ?
C21 N21 H21C 109.5 . . ?
H21A N21 H21C 109.5 . . ?
H21B N21 H21C 109.5 . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
N21 H21C O1B  0.91 1.87 2.770(5) 170.5 .
N4 H4A O1C  0.88 2.19 3.050(6) 164.1 2_575
N4 H4A S1  0.88 3.01 3.873(5) 168.3 2_575
N4 H4B O1A  0.88 2.45 3.328(6) 173.6 4_466
N21 H21A O1A  0.91 1.90 2.765(6) 158.5 3_645
N21 H21B O1C  0.91 1.96 2.840(6) 160.9 3_545
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.47
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    1.126
_refine_diff_density_min   -0.471
_refine_diff_density_rms    0.107
