 
data_06skc0018p21c
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Ethanol-2-ammonium toluene-4-sulphonate
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C9 H15 N O4 S'
_chemical_formula_weight          233.28
 
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/c
 
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'
 
_cell_length_a                    13.730(2)
_cell_length_b                    5.8676(6)
_cell_length_c                    15.418(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  115.604(6)
_cell_angle_gamma                 90.00
_cell_volume                      1120.2(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3834
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        shard
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.08
_exptl_crystal_size_mid           0.05
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.383
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              496
_exptl_absorpt_coefficient_mu     0.284
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9777
_exptl_absorpt_correction_T_max   0.9972
_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             18266
_diffrn_reflns_av_R_equivalents   0.1326
_diffrn_reflns_av_sigmaI/netI     0.0960
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          2.93
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2567
_reflns_number_gt                 1818
_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)+(0.0305P)²+2.9053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2567
_refine_ls_number_parameters      141
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1504
_refine_ls_R_factor_gt            0.1002
_refine_ls_wR_factor_ref          0.1711
_refine_ls_wR_factor_gt           0.1562
_refine_ls_goodness_of_fit_ref    1.176
_refine_ls_restrained_S_all       1.176
_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
C4 C 0.5403(4) 0.4085(8) 0.1194(3) 0.0277(11) Uani 1 1 d . . .
C3 C 0.5191(4) 0.6128(8) 0.1533(3) 0.0307(11) Uani 1 1 d . . .
H3 H 0.5736 0.7264 0.1770 0.037 Uiso 1 1 calc R . .
C2 C 0.4196(3) 0.6537(8) 0.1532(3) 0.0282(10) Uani 1 1 d . . .
H2 H 0.4062 0.7942 0.1767 0.034 Uiso 1 1 calc R . .
C1 C 0.3402(3) 0.4890(7) 0.1187(3) 0.0230(10) Uani 1 1 d . . .
C6 C 0.3593(4) 0.2823(7) 0.0853(3) 0.0291(11) Uani 1 1 d . . .
H6 H 0.3046 0.1688 0.0619 0.035 Uiso 1 1 calc R . .
C5 C 0.4592(4) 0.2444(8) 0.0866(3) 0.0320(11) Uani 1 1 d . . .
H5 H 0.4730 0.1023 0.0645 0.038 Uiso 1 1 calc R . .
C7 C 0.6476(4) 0.3641(9) 0.1184(4) 0.0410(13) Uani 1 1 d . . .
H7A H 0.6363 0.3198 0.0535 0.062 Uiso 1 1 calc R . .
H7B H 0.6848 0.2409 0.1635 0.062 Uiso 1 1 calc R . .
H7C H 0.6917 0.5028 0.1376 0.062 Uiso 1 1 calc R . .
O1A O 0.1338(2) 0.4182(5) 0.0330(2) 0.0293(7) Uani 1 1 d . . .
O1B O 0.2136(2) 0.4580(5) 0.2058(2) 0.0315(7) Uani 1 1 d . . .
O1C O 0.1970(2) 0.7888(5) 0.1067(2) 0.0297(7) Uani 1 1 d . . .
S1 S 0.21141(9) 0.54259(18) 0.11588(8) 0.0240(3) Uani 1 1 d . . .
C23 C -0.0216(3) 0.0499(8) 0.1072(3) 0.0281(10) Uani 1 1 d . . .
H23A H -0.0427 -0.1123 0.0940 0.034 Uiso 1 1 calc R . .
H23B H -0.0240 0.1180 0.0475 0.034 Uiso 1 1 calc R . .
C22 C -0.1007(4) 0.1718(8) 0.1347(3) 0.0285(10) Uani 1 1 d . . .
H22A H -0.1748 0.1498 0.0836 0.034 Uiso 1 1 calc R . .
H22B H -0.0976 0.1051 0.1949 0.034 Uiso 1 1 calc R . .
N24 N 0.0906(3) 0.0650(6) 0.1848(2) 0.0272(8) Uani 1 1 d . . .
H24A H 0.1150 0.2105 0.1888 0.041 Uiso 1 1 calc R . .
H24B H 0.1343 -0.0307 0.1712 0.041 Uiso 1 1 calc R . .
H24C H 0.0909 0.0244 0.2419 0.041 Uiso 1 1 calc R . .
O21 O -0.0778(3) 0.4084(5) 0.1483(2) 0.0297(8) Uani 1 1 d . . .
H21 H -0.083(4) 0.473(9) 0.102(4) 0.044 Uiso 1 1 d . . .
 
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
C4 0.029(2) 0.033(3) 0.020(2) 0.0109(19) 0.010(2) 0.009(2)
C3 0.033(3) 0.031(3) 0.025(2) 0.003(2) 0.010(2) -0.004(2)
C2 0.031(3) 0.023(2) 0.027(2) -0.002(2) 0.010(2) 0.002(2)
C1 0.030(2) 0.021(2) 0.021(2) 0.0024(18) 0.0141(19) 0.0021(18)
C6 0.039(3) 0.017(2) 0.035(3) 0.002(2) 0.019(2) -0.0008(19)
C5 0.043(3) 0.025(2) 0.034(3) 0.005(2) 0.022(2) 0.012(2)
C7 0.027(3) 0.061(4) 0.032(3) 0.010(2) 0.009(2) 0.011(2)
O1A 0.0304(17) 0.0254(18) 0.0297(17) -0.0022(14) 0.0107(14) -0.0010(13)
O1B 0.0388(18) 0.0317(18) 0.0270(16) -0.0027(14) 0.0171(15) -0.0066(15)
O1C 0.0331(17) 0.0206(16) 0.0369(18) 0.0007(14) 0.0165(15) 0.0045(14)
S1 0.0276(6) 0.0195(5) 0.0260(6) -0.0007(5) 0.0127(5) 0.0002(5)
C23 0.033(2) 0.025(2) 0.028(2) -0.001(2) 0.014(2) -0.001(2)
C22 0.030(2) 0.028(3) 0.024(2) 0.001(2) 0.009(2) -0.001(2)
N24 0.035(2) 0.022(2) 0.028(2) 0.0019(16) 0.0173(17) 0.0044(17)
O21 0.0428(19) 0.0220(18) 0.0279(17) -0.0014(13) 0.0188(16) 0.0025(14)
 
_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 C3 1.388(6) . ?
C4 C5 1.391(6) . ?
C4 C7 1.503(6) . ?
C3 C2 1.386(6) . ?
C3 H3 0.9500 . ?
C2 C1 1.380(6) . ?
C2 H2 0.9500 . ?
C1 C6 1.387(6) . ?
C1 S1 1.777(4) . ?
C6 C5 1.381(6) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
O1A S1 1.458(3) . ?
O1B S1 1.461(3) . ?
O1C S1 1.457(3) . ?
C23 N24 1.490(5) . ?
C23 C22 1.508(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C22 O21 1.419(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N24 H24A 0.9100 . ?
N24 H24B 0.9100 . ?
N24 H24C 0.9100 . ?
O21 H21 0.78(5) . ?
 
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
C3 C4 C5 118.0(4) . . ?
C3 C4 C7 121.3(4) . . ?
C5 C4 C7 120.7(4) . . ?
C2 C3 C4 121.0(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C1 C2 C3 119.6(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C1 C6 120.7(4) . . ?
C2 C1 S1 119.9(3) . . ?
C6 C1 S1 119.4(3) . . ?
C5 C6 C1 118.8(4) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
C6 C5 C4 121.9(4) . . ?
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 113.19(18) . . ?
O1C S1 O1B 112.07(19) . . ?
O1A S1 O1B 111.72(18) . . ?
O1C S1 C1 105.62(19) . . ?
O1A S1 C1 105.99(19) . . ?
O1B S1 C1 107.70(19) . . ?
N24 C23 C22 111.4(3) . . ?
N24 C23 H23A 109.3 . . ?
C22 C23 H23A 109.3 . . ?
N24 C23 H23B 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
O21 C22 C23 111.4(4) . . ?
O21 C22 H22A 109.4 . . ?
C23 C22 H22A 109.4 . . ?
O21 C22 H22B 109.4 . . ?
C23 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C23 N24 H24A 109.5 . . ?
C23 N24 H24B 109.5 . . ?
H24A N24 H24B 109.5 . . ?
C23 N24 H24C 109.5 . . ?
H24A N24 H24C 109.5 . . ?
H24B N24 H24C 109.5 . . ?
C22 O21 H21 114(4) . . ?
 
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
N24 H24A O1B  0.91 1.92 2.794(5) 159.2 .
N24 H24A S1  0.91 2.85 3.642(4) 146.8 .
N24 H24B O1C  0.91 1.90 2.782(5) 163.7 1_545
N24 H24B S1  0.91 2.98 3.848(4) 159.2 1_545
N24 H24C O21  0.91 1.90 2.807(5) 172.2 2_545
O21 H21 O1A  0.78(5) 1.99(5) 2.753(4) 164(5) 3_565
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.356
_refine_diff_density_min   -0.408
_refine_diff_density_rms    0.082
