 
data_06skc0016p-1
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
1,1,3,3-Tetramethylbutylammonium toluene-4-sulphonate
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C15 H27 N O3 S'
_chemical_formula_weight          301.44
 
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'
 'S'  'S'   0.1246   0.1234
 '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'
 
_symmetry_cell_setting            triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    6.1332(4)
_cell_length_b                    10.2547(7)
_cell_length_c                    13.7444(6)
_cell_angle_alpha                 98.274(3)
_cell_angle_beta                  93.850(4)
_cell_angle_gamma                 94.425(3)
_cell_volume                      850.21(9)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3727
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        lath
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.14
_exptl_crystal_size_mid           0.05
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.177
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              328
_exptl_absorpt_coefficient_mu     0.197
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9729
_exptl_absorpt_correction_T_max   0.9980
_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             15025
_diffrn_reflns_av_R_equivalents   0.0775
_diffrn_reflns_av_sigmaI/netI     0.0790
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.00
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3857
_reflns_number_gt                 2713
_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)+(0.0339P)²+0.6082P] 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_number_reflns          3857
_refine_ls_number_parameters      188
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0932
_refine_ls_R_factor_gt            0.0568
_refine_ls_wR_factor_ref          0.1242
_refine_ls_wR_factor_gt           0.1115
_refine_ls_goodness_of_fit_ref    1.027
_refine_ls_restrained_S_all       1.027
_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 0.4584(4) 0.3087(2) 0.95904(16) 0.0291(6) Uani 1 1 d . . .
C3 C 0.5993(4) 0.3140(2) 0.88520(17) 0.0301(6) Uani 1 1 d . . .
H3 H 0.7363 0.2774 0.8914 0.036 Uiso 1 1 calc R . .
C2 C 0.5464(4) 0.3716(2) 0.80210(17) 0.0274(5) Uani 1 1 d . . .
H2 H 0.6455 0.3741 0.7520 0.033 Uiso 1 1 calc R . .
C1 C 0.3459(4) 0.4255(2) 0.79350(16) 0.0220(5) Uani 1 1 d . . .
C6 C 0.2037(4) 0.4230(2) 0.86688(16) 0.0270(5) Uani 1 1 d . . .
H6 H 0.0677 0.4609 0.8611 0.032 Uiso 1 1 calc R . .
C5 C 0.2597(4) 0.3649(2) 0.94906(17) 0.0304(6) Uani 1 1 d . . .
H5 H 0.1611 0.3633 0.9994 0.037 Uiso 1 1 calc R . .
C7 C 0.5162(5) 0.2409(3) 1.04653(19) 0.0427(7) Uani 1 1 d . . .
H7A H 0.4769 0.1455 1.0292 0.064 Uiso 1 1 calc R . .
H7B H 0.4351 0.2759 1.1021 0.064 Uiso 1 1 calc R . .
H7C H 0.6741 0.2572 1.0651 0.064 Uiso 1 1 calc R . .
S1 S 0.27770(9) 0.50013(6) 0.68833(4) 0.02271(16) Uani 1 1 d . . .
O1A O 0.3782(3) 0.42614(16) 0.60694(11) 0.0301(4) Uani 1 1 d . . .
O1B O 0.3735(3) 0.63686(15) 0.70940(11) 0.0252(4) Uani 1 1 d . . .
O1C O 0.0396(3) 0.48913(17) 0.67587(13) 0.0346(4) Uani 1 1 d . . .
C24 C -0.1590(4) -0.2064(2) 0.60201(16) 0.0209(5) Uani 1 1 d . . .
C23 C -0.1223(4) -0.1568(2) 0.71385(16) 0.0233(5) Uani 1 1 d . . .
H23A H -0.0454 -0.2250 0.7432 0.028 Uiso 1 1 calc R . .
H23B H -0.2693 -0.1574 0.7395 0.028 Uiso 1 1 calc R . .
C22 C 0.0017(4) -0.0218(2) 0.75771(16) 0.0254(5) Uani 1 1 d . . .
C21 C -0.0390(4) -0.0016(3) 0.86731(17) 0.0339(6) Uani 1 1 d . . .
H21A H 0.0442 0.0800 0.9004 0.051 Uiso 1 1 calc R . .
H21B H 0.0086 -0.0769 0.8972 0.051 Uiso 1 1 calc R . .
H21C H -0.1958 0.0050 0.8745 0.051 Uiso 1 1 calc R . .
C28 C 0.0493(4) -0.2103(2) 0.54749(16) 0.0250(5) Uani 1 1 d . . .
H28A H 0.1591 -0.2534 0.5837 0.037 Uiso 1 1 calc R . .
H28B H 0.1070 -0.1199 0.5426 0.037 Uiso 1 1 calc R . .
H28C H 0.0157 -0.2602 0.4811 0.037 Uiso 1 1 calc R . .
C29 C -0.3334(4) -0.1380(2) 0.54864(17) 0.0265(5) Uani 1 1 d . . .
H29A H -0.3636 -0.1831 0.4807 0.040 Uiso 1 1 calc R . .
H29B H -0.2801 -0.0455 0.5481 0.040 Uiso 1 1 calc R . .
H29C H -0.4683 -0.1413 0.5829 0.040 Uiso 1 1 calc R . .
C27 C -0.0807(5) 0.0945(2) 0.71251(18) 0.0344(6) Uani 1 1 d . . .
H27A H -0.2402 0.0930 0.7149 0.052 Uiso 1 1 calc R . .
H27B H -0.0439 0.0876 0.6438 0.052 Uiso 1 1 calc R . .
H27C H -0.0109 0.1776 0.7498 0.052 Uiso 1 1 calc R . .
C26 C 0.2501(4) -0.0213(3) 0.7502(2) 0.0370(6) Uani 1 1 d . . .
H26A H 0.2832 -0.0182 0.6818 0.056 Uiso 1 1 calc R . .
H26B H 0.3013 -0.1017 0.7713 0.056 Uiso 1 1 calc R . .
H26C H 0.3246 0.0565 0.7928 0.056 Uiso 1 1 calc R . .
N25 N -0.2532(3) -0.34836(17) 0.59509(13) 0.0214(4) Uani 1 1 d . . .
H25A H -0.2927 -0.3820 0.5309 0.032 Uiso 1 1 calc R . .
H25B H -0.3731 -0.3516 0.6305 0.032 Uiso 1 1 calc R . .
H25C H -0.1504 -0.3969 0.6197 0.032 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 C3 1.381(3) . ?
C4 C5 1.394(4) . ?
C4 C7 1.509(3) . ?
C3 C2 1.390(3) . ?
C3 H3 0.9500 . ?
C2 C1 1.392(3) . ?
C2 H2 0.9500 . ?
C1 C6 1.379(3) . ?
C1 S1 1.771(2) . ?
C6 C5 1.386(3) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
S1 O1C 1.4525(17) . ?
S1 O1A 1.4585(17) . ?
S1 O1B 1.4588(16) . ?
C24 N25 1.512(3) . ?
C24 C28 1.524(3) . ?
C24 C29 1.527(3) . ?
C24 C23 1.544(3) . ?
C23 C22 1.547(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C22 C27 1.526(3) . ?
C22 C21 1.531(3) . ?
C22 C26 1.534(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N25 H25A 0.9100 . ?
N25 H25B 0.9100 . ?
N25 H25C 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
C3 C4 C5 118.1(2) . . ?
C3 C4 C7 120.7(2) . . ?
C5 C4 C7 121.2(2) . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C6 C1 C2 120.3(2) . . ?
C6 C1 S1 120.39(18) . . ?
C2 C1 S1 119.25(17) . . ?
C1 C6 C5 119.8(2) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
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 113.44(10) . . ?
O1C S1 O1B 113.00(10) . . ?
O1A S1 O1B 111.18(10) . . ?
O1C S1 C1 105.87(10) . . ?
O1A S1 C1 105.98(10) . . ?
O1B S1 C1 106.74(10) . . ?
N25 C24 C28 106.26(18) . . ?
N25 C24 C29 105.13(17) . . ?
C28 C24 C29 111.05(18) . . ?
N25 C24 C23 104.35(16) . . ?
C28 C24 C23 114.90(18) . . ?
C29 C24 C23 114.08(19) . . ?
C24 C23 C22 123.26(18) . . ?
C24 C23 H23A 106.5 . . ?
C22 C23 H23A 106.5 . . ?
C24 C23 H23B 106.5 . . ?
C22 C23 H23B 106.5 . . ?
H23A C23 H23B 106.5 . . ?
C27 C22 C21 108.2(2) . . ?
C27 C22 C26 109.0(2) . . ?
C21 C22 C26 107.7(2) . . ?
C27 C22 C23 113.7(2) . . ?
C21 C22 C23 105.55(18) . . ?
C26 C22 C23 112.4(2) . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C24 C29 H29A 109.5 . . ?
C24 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C24 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 N25 H25A 109.5 . . ?
C24 N25 H25B 109.5 . . ?
H25A N25 H25B 109.5 . . ?
C24 N25 H25C 109.5 . . ?
H25A N25 H25C 109.5 . . ?
H25B N25 H25C 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
N25 H25A O1A  0.91 1.91 2.814(2) 171.5 2_556
N25 H25B O1B  0.91 1.96 2.869(2) 177.9 1_445
N25 H25B O1A  0.91 2.61 3.136(2) 117.6 1_445
N25 H25B S1  0.91 2.76 3.5655(18) 148.5 1_445
N25 H25C O1C  0.91 1.92 2.822(2) 173.7 1_545
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.286
_refine_diff_density_min   -0.420
_refine_diff_density_rms    0.061
