 
data_06skc0019p21
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Toluidinium toluene-4-sulphonate
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H17 N O3 S'
_chemical_formula_weight          279.35
 
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            monoclinic
_symmetry_space_group_name_H-M    P21
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    5.6889(4)
_cell_length_b                    8.9638(4)
_cell_length_c                    13.2457(11)
_cell_angle_alpha                 90.00
_cell_angle_beta                  97.112(3)
_cell_angle_gamma                 90.00
_cell_volume                      670.26(8)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     1606
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.07
_exptl_crystal_size_mid           0.05
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.384
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              296
_exptl_absorpt_coefficient_mu     0.245
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9831
_exptl_absorpt_correction_T_max   0.9976
_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             8540
_diffrn_reflns_av_R_equivalents   0.0772
_diffrn_reflns_av_sigmaI/netI     0.1010
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.10
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2844
_reflns_number_gt                 2227
_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.
;
 
_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)+(0.0363P)²+0.1238P] 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    -0.14(10)
_refine_ls_number_reflns          2844
_refine_ls_number_parameters      175
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0831
_refine_ls_R_factor_gt            0.0579
_refine_ls_wR_factor_ref          0.1066
_refine_ls_wR_factor_gt           0.0980
_refine_ls_goodness_of_fit_ref    1.035
_refine_ls_restrained_S_all       1.035
_refine_ls_shift/su_max           0.001
_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
C4 C 0.3768(6) 0.3728(4) 0.5524(3) 0.0200(8) Uani 1 1 d . . .
C3 C 0.2334(6) 0.2692(4) 0.5943(3) 0.0212(8) Uani 1 1 d . . .
H3 H 0.0783 0.2503 0.5614 0.025 Uiso 1 1 calc R . .
C2 C 0.3132(6) 0.1938(4) 0.6828(3) 0.0195(8) Uani 1 1 d . . .
H2 H 0.2127 0.1244 0.7107 0.023 Uiso 1 1 calc R . .
C1 C 0.5409(6) 0.2194(3) 0.7310(3) 0.0152(7) Uani 1 1 d . . .
C6 C 0.6883(6) 0.3215(4) 0.6897(3) 0.0167(8) Uani 1 1 d . . .
H6 H 0.8443 0.3394 0.7219 0.020 Uiso 1 1 calc R . .
C5 C 0.6038(6) 0.3961(4) 0.6012(3) 0.0206(8) Uani 1 1 d . . .
H5 H 0.7042 0.4653 0.5730 0.025 Uiso 1 1 calc R . .
C7 C 0.2878(7) 0.4557(4) 0.4563(3) 0.0276(9) Uani 1 1 d . . .
H7A H 0.1142 0.4549 0.4468 0.041 Uiso 1 1 calc R . .
H7B H 0.3468 0.4071 0.3981 0.041 Uiso 1 1 calc R . .
H7C H 0.3444 0.5590 0.4615 0.041 Uiso 1 1 calc R . .
O1A O 0.8979(3) 0.1147(3) 0.84776(17) 0.0228(5) Uani 1 1 d . . .
O1B O 0.5737(4) 0.2192(2) 0.92857(18) 0.0217(6) Uani 1 1 d . . .
O1C O 0.5220(4) -0.0172(2) 0.84222(19) 0.0216(6) Uani 1 1 d . . .
S1 S 0.64288(14) 0.12546(9) 0.84588(6) 0.0168(2) Uani 1 1 d . . .
C24 C 1.1450(6) 0.6653(3) 0.7684(3) 0.0203(8) Uani 1 1 d . . .
C23 C 1.2171(6) 0.5346(4) 0.8183(3) 0.0216(8) Uani 1 1 d . . .
H23 H 1.3516 0.4834 0.7999 0.026 Uiso 1 1 calc R . .
C22 C 1.0981(6) 0.4766(4) 0.8946(3) 0.0193(8) Uani 1 1 d . . .
H22 H 1.1500 0.3868 0.9283 0.023 Uiso 1 1 calc R . .
C21 C 0.9019(6) 0.5520(4) 0.9207(3) 0.0179(8) Uani 1 1 d . . .
C26 C 0.8267(6) 0.6819(4) 0.8728(3) 0.0222(8) Uani 1 1 d . . .
H26 H 0.6911 0.7323 0.8909 0.027 Uiso 1 1 calc R . .
C25 C 0.9500(6) 0.7393(4) 0.7977(3) 0.0238(8) Uani 1 1 d . . .
H25 H 0.9003 0.8307 0.7657 0.029 Uiso 1 1 calc R . .
C27 C 1.2740(7) 0.7264(4) 0.6846(3) 0.0269(9) Uani 1 1 d . . .
H27A H 1.2953 0.8343 0.6935 0.040 Uiso 1 1 calc R . .
H27B H 1.1812 0.7065 0.6186 0.040 Uiso 1 1 calc R . .
H27C H 1.4292 0.6782 0.6871 0.040 Uiso 1 1 calc R . .
N21 N 0.7765(5) 0.4915(3) 1.0018(2) 0.0198(7) Uani 1 1 d . . .
H21A H 0.8776 0.4861 1.0605 0.030 Uiso 1 1 calc R . .
H21B H 0.7213 0.3987 0.9841 0.030 Uiso 1 1 calc R . .
H21C H 0.6528 0.5522 1.0111 0.030 Uiso 1 1 calc R . .
 
 
_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
C4 C5 1.386(5) . ?
C4 C3 1.396(5) . ?
C4 C7 1.506(5) . ?
C3 C2 1.380(5) . ?
C3 H3 0.9500 . ?
C2 C1 1.390(4) . ?
C2 H2 0.9500 . ?
C1 C6 1.398(4) . ?
C1 S1 1.773(3) . ?
C6 C5 1.383(5) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
O1A S1 1.451(2) . ?
O1B S1 1.472(2) . ?
O1C S1 1.450(2) . ?
C24 C23 1.382(5) . ?
C24 C25 1.388(5) . ?
C24 C27 1.508(5) . ?
C23 C22 1.385(5) . ?
C23 H23 0.9500 . ?
C22 C21 1.384(5) . ?
C22 H22 0.9500 . ?
C21 C26 1.369(5) . ?
C21 N21 1.465(4) . ?
C26 C25 1.385(5) . ?
C26 H26 0.9500 . ?
C25 H25 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
C5 C4 C3 118.1(3) . . ?
C5 C4 C7 121.0(3) . . ?
C3 C4 C7 120.8(3) . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C1 C6 119.9(3) . . ?
C2 C1 S1 120.2(3) . . ?
C6 C1 S1 119.9(2) . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C6 C5 C4 121.9(3) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1C S1 O1A 114.27(15) . . ?
O1C S1 O1B 111.01(14) . . ?
O1A S1 O1B 112.59(14) . . ?
O1C S1 C1 106.65(15) . . ?
O1A S1 C1 105.46(14) . . ?
O1B S1 C1 106.17(15) . . ?
C23 C24 C25 118.1(3) . . ?
C23 C24 C27 121.2(3) . . ?
C25 C24 C27 120.7(3) . . ?
C24 C23 C22 121.6(3) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C21 C22 C23 118.7(3) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C26 C21 C22 121.0(4) . . ?
C26 C21 N21 120.1(3) . . ?
C22 C21 N21 118.9(3) . . ?
C21 C26 C25 119.4(4) . . ?
C21 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C25 C24 121.1(3) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
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 H21B O1B  0.91 1.92 2.820(4) 170.6 .
N21 H21A O1A  0.91 2.01 2.776(4) 140.6 2_757
N21 H21C O1B  0.91 2.19 3.072(4) 163.4 2_657
N21 H21C O1C  0.91 2.37 2.833(4) 111.4 2_657
N21 H21C S1  0.91 2.76 3.521(3) 141.4 2_657
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.337
_refine_diff_density_min   -0.354
_refine_diff_density_rms    0.075
