 
data_06skc0022p21c
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Ethanol-2-ammonium naphthalenesulphonate
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H15 N O4 S'
_chemical_formula_weight          269.31
 
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                    13.7465(12)
_cell_length_b                    8.6976(8)
_cell_length_c                    10.3290(6)
_cell_angle_alpha                 90.00
_cell_angle_beta                  97.361(5)
_cell_angle_gamma                 90.00
_cell_volume                      1224.77(17)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2904
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.06
_exptl_crystal_size_mid           0.04
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.461
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              568
_exptl_absorpt_coefficient_mu     0.271
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9839
_exptl_absorpt_correction_T_max   0.9973
_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             14900
_diffrn_reflns_av_R_equivalents   0.1299
_diffrn_reflns_av_sigmaI/netI     0.1129
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          2.99
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2804
_reflns_number_gt                 1790
_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)+(0.0348P)²+0.9572P] 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          2804
_refine_ls_number_parameters      165
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1242
_refine_ls_R_factor_gt            0.0661
_refine_ls_wR_factor_ref          0.1261
_refine_ls_wR_factor_gt           0.1096
_refine_ls_goodness_of_fit_ref    1.043
_refine_ls_restrained_S_all       1.043
_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 0.8617(2) 0.0757(4) 0.1538(3) 0.0166(7) Uani 1 1 d . . .
H1 H 0.8463 -0.0038 0.2108 0.020 Uiso 1 1 calc R . .
C2 C 0.7883(2) 0.1628(3) 0.0887(3) 0.0145(7) Uani 1 1 d . . .
C3 C 0.8089(2) 0.2800(4) 0.0009(3) 0.0193(7) Uani 1 1 d . . .
H3 H 0.7572 0.3380 -0.0454 0.023 Uiso 1 1 calc R . .
C4 C 0.9043(2) 0.3085(4) -0.0162(3) 0.0195(7) Uani 1 1 d . . .
H4 H 0.9181 0.3872 -0.0751 0.023 Uiso 1 1 calc R . .
C5 C 0.9828(2) 0.2242(4) 0.0512(3) 0.0179(7) Uani 1 1 d . . .
C6 C 1.0821(2) 0.2550(4) 0.0392(3) 0.0229(8) Uani 1 1 d . . .
H6 H 1.0977 0.3343 -0.0179 0.027 Uiso 1 1 calc R . .
C7 C 1.1561(3) 0.1730(4) 0.1080(3) 0.0247(8) Uani 1 1 d . . .
H7 H 1.2225 0.1978 0.1007 0.030 Uiso 1 1 calc R . .
C8 C 1.1342(3) 0.0513(4) 0.1900(3) 0.0234(8) Uani 1 1 d . . .
H8 H 1.1859 -0.0073 0.2359 0.028 Uiso 1 1 calc R . .
C9 C 1.0390(2) 0.0175(4) 0.2038(3) 0.0207(7) Uani 1 1 d . . .
H9 H 1.0249 -0.0647 0.2590 0.025 Uiso 1 1 calc R . .
C10 C 0.9612(2) 0.1037(4) 0.1364(3) 0.0161(7) Uani 1 1 d . . .
O2A O 0.61832(16) 0.0568(3) -0.0072(2) 0.0230(5) Uani 1 1 d . . .
O2B O 0.66502(16) 0.0310(3) 0.2258(2) 0.0242(6) Uani 1 1 d . . .
O2C O 0.62349(16) 0.2820(3) 0.1302(2) 0.0263(6) Uani 1 1 d . . .
S2 S 0.66515(6) 0.13067(9) 0.11268(7) 0.0182(2) Uani 1 1 d . . .
C22 C 1.3576(2) 0.1626(4) 0.4268(3) 0.0202(7) Uani 1 1 d . . .
H22A H 1.3035 0.2211 0.3768 0.024 Uiso 1 1 calc R . .
H22B H 1.3315 0.0611 0.4487 0.024 Uiso 1 1 calc R . .
C23 C 1.4389(2) 0.1399(4) 0.3430(3) 0.0205(7) Uani 1 1 d . . .
H23A H 1.4914 0.0760 0.3907 0.025 Uiso 1 1 calc R . .
H23B H 1.4129 0.0847 0.2621 0.025 Uiso 1 1 calc R . .
N24 N 1.48093(19) 0.2912(3) 0.3084(2) 0.0189(6) Uani 1 1 d . . .
H24A H 1.5186 0.3304 0.3796 0.028 Uiso 1 1 calc R . .
H24B H 1.4313 0.3577 0.2818 0.028 Uiso 1 1 calc R . .
H24C H 1.5184 0.2774 0.2428 0.028 Uiso 1 1 calc R . .
O21 O 1.39078(17) 0.2428(3) 0.54390(19) 0.0223(5) Uani 1 1 d . . .
H21 H 1.3896 0.3378 0.5293 0.033 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
C1 C2 1.368(4) . ?
C1 C10 1.423(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.417(4) . ?
C2 S2 1.764(3) . ?
C3 C4 1.368(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.412(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(4) . ?
C5 C10 1.424(4) . ?
C6 C7 1.365(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.412(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.367(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.413(4) . ?
C9 H9 0.9500 . ?
O2A S2 1.469(2) . ?
O2B S2 1.455(2) . ?
O2C S2 1.456(2) . ?
C22 O21 1.420(4) . ?
C22 C23 1.512(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 N24 1.499(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
N24 H24A 0.9100 . ?
N24 H24B 0.9100 . ?
N24 H24C 0.9100 . ?
O21 H21 0.8400 . ?
 
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 C10 120.3(3) . . ?
C2 C1 H1 119.8 . . ?
C10 C1 H1 119.8 . . ?
C1 C2 C3 121.1(3) . . ?
C1 C2 S2 120.3(2) . . ?
C3 C2 S2 118.6(2) . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 123.0(3) . . ?
C6 C5 C10 118.3(3) . . ?
C4 C5 C10 118.8(3) . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C1 121.7(3) . . ?
C9 C10 C5 119.4(3) . . ?
C1 C10 C5 118.9(3) . . ?
O2B S2 O2C 113.44(14) . . ?
O2B S2 O2A 111.77(14) . . ?
O2C S2 O2A 111.32(14) . . ?
O2B S2 C2 107.87(14) . . ?
O2C S2 C2 105.91(14) . . ?
O2A S2 C2 106.01(13) . . ?
O21 C22 C23 111.8(3) . . ?
O21 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
O21 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
N24 C23 C22 110.9(3) . . ?
N24 C23 H23A 109.5 . . ?
C22 C23 H23A 109.5 . . ?
N24 C23 H23B 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 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 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
N24 H24A O2A  0.91 1.95 2.832(3) 163.2 4_666
N24 H24A S2  0.91 2.95 3.836(3) 163.7 4_666
N24 H24B O2B  0.91 2.00 2.884(3) 163.2 2_755
N24 H24B S2  0.91 2.99 3.719(3) 138.1 2_755
O21 H21 O2A  0.84 1.92 2.758(3) 175.6 2_755
O21 H21 S2  0.84 2.99 3.778(2) 157.7 2_755
N24 H24C O2C  0.91 1.97 2.856(3) 165.0 1_655
N24 H24C S2  0.91 2.86 3.710(3) 155.3 1_655
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.406
_refine_diff_density_min   -0.397
_refine_diff_density_rms    0.080
