 
data_06skc0076p21c
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Sodium aniline-2-sulphonate
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C6 H6 N Na O3 S'
_chemical_formula_weight          195.17
 
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'
 'Na'  'Na'   0.0362   0.0249
 '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                    14.0939(6)
_cell_length_b                    4.9227(2)
_cell_length_c                    11.3731(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  97.321(3)
_cell_angle_gamma                 90.00
_cell_volume                      782.63(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3305
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.13
_exptl_crystal_size_mid           0.09
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.656
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              400
_exptl_absorpt_coefficient_mu     0.428
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9464
_exptl_absorpt_correction_T_max   0.9915
_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             11452
_diffrn_reflns_av_R_equivalents   0.0716
_diffrn_reflns_av_sigmaI/netI     0.0478
_diffrn_reflns_limit_h_min        -18
_diffrn_reflns_limit_h_max        18
_diffrn_reflns_limit_k_min        -6
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          2.91
_diffrn_reflns_theta_max          27.48
_reflns_number_total              1804
_reflns_number_gt                 1450
_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)+(0.0281P)²+2.0031P] 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          1804
_refine_ls_number_parameters      109
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0716
_refine_ls_R_factor_gt            0.0520
_refine_ls_wR_factor_ref          0.1150
_refine_ls_wR_factor_gt           0.1058
_refine_ls_goodness_of_fit_ref    1.078
_refine_ls_restrained_S_all       1.078
_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
Na1 Na 0.55368(8) -0.0167(2) 0.13363(9) 0.0188(3) Uani 1 1 d . . .
C1 C 0.7394(2) 0.0020(6) 0.3915(3) 0.0183(6) Uani 1 1 d . . .
C2 C 0.7549(2) -0.1705(6) 0.2972(3) 0.0200(6) Uani 1 1 d . . .
C3 C 0.8452(2) -0.1649(7) 0.2579(3) 0.0292(7) Uani 1 1 d . . .
H3 H 0.8572 -0.2766 0.1933 0.035 Uiso 1 1 calc R . .
C4 C 0.9166(2) 0.0003(8) 0.3117(4) 0.0377(9) Uani 1 1 d . . .
H4 H 0.9772 0.0023 0.2833 0.045 Uiso 1 1 calc R . .
C5 C 0.9015(3) 0.1644(8) 0.4072(4) 0.0374(9) Uani 1 1 d . . .
H5 H 0.9518 0.2737 0.4452 0.045 Uiso 1 1 calc R . .
C6 C 0.8126(2) 0.1671(7) 0.4460(3) 0.0263(7) Uani 1 1 d . . .
H6 H 0.8013 0.2815 0.5100 0.032 Uiso 1 1 calc R . .
N2 N 0.68171(17) -0.3289(5) 0.2410(2) 0.0203(5) Uani 1 1 d . . .
H1 H 0.6914 -0.4287 0.1794 0.024 Uiso 1 1 calc R . .
H2 H 0.6255 -0.3300 0.2668 0.024 Uiso 1 1 calc R . .
O1A O 0.63435(16) 0.1941(4) 0.54069(17) 0.0211(5) Uani 1 1 d . . .
O1B O 0.56581(14) 0.1652(4) 0.33339(16) 0.0178(4) Uani 1 1 d . . .
O1C O 0.58876(15) -0.2442(4) 0.45187(17) 0.0195(5) Uani 1 1 d . . .
S1 S 0.62342(5) 0.03062(14) 0.43344(6) 0.01591(19) Uani 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
Na1 0.0245(6) 0.0175(6) 0.0142(5) 0.0006(5) 0.0019(4) -0.0013(5)
C1 0.0189(14) 0.0166(14) 0.0187(13) 0.0020(12) 0.0003(11) 0.0034(11)
C2 0.0241(15) 0.0165(15) 0.0194(14) 0.0009(12) 0.0033(12) 0.0032(12)
C3 0.0275(17) 0.0274(18) 0.0338(18) -0.0010(15) 0.0084(14) 0.0034(14)
C4 0.0218(17) 0.034(2) 0.059(2) -0.0035(18) 0.0125(16) -0.0002(15)
C5 0.0254(17) 0.031(2) 0.054(2) -0.0067(18) -0.0014(16) -0.0069(15)
C6 0.0265(16) 0.0202(16) 0.0307(17) -0.0033(14) -0.0026(14) -0.0017(13)
N2 0.0212(13) 0.0228(14) 0.0171(12) -0.0072(11) 0.0035(10) 0.0001(11)
O1A 0.0358(12) 0.0154(10) 0.0121(10) -0.0018(8) 0.0027(9) 0.0022(9)
O1B 0.0233(10) 0.0164(10) 0.0133(9) 0.0011(8) 0.0014(8) 0.0033(8)
O1C 0.0274(11) 0.0141(10) 0.0177(10) 0.0016(8) 0.0063(8) -0.0015(8)
S1 0.0227(4) 0.0130(3) 0.0121(3) 0.0002(3) 0.0022(3) 0.0011(3)
 
_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
Na1 O1A 2.289(2) 4_565 ?
Na1 O1B 2.364(2) 2_645 ?
Na1 O1B 2.428(2) . ?
Na1 O1C 2.482(2) 4 ?
Na1 O1C 2.505(2) 2_655 ?
Na1 N2 2.559(3) . ?
Na1 Na1 3.222(2) 3_655 ?
Na1 S1 3.3603(13) 2_645 ?
Na1 Na1 4.0466(17) 2_655 ?
Na1 Na1 4.0466(17) 2_645 ?
C1 C6 1.395(4) . ?
C1 C2 1.407(4) . ?
C1 S1 1.766(3) . ?
C2 N2 1.383(4) . ?
C2 C3 1.401(4) . ?
C3 C4 1.376(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N2 H1 0.8800 . ?
N2 H2 0.8800 . ?
O1A S1 1.453(2) . ?
O1A Na1 2.289(2) 4_566 ?
O1B S1 1.469(2) . ?
O1B Na1 2.364(2) 2_655 ?
O1C S1 1.463(2) . ?
O1C Na1 2.482(2) 4_556 ?
O1C Na1 2.505(2) 2_645 ?
S1 Na1 3.3603(13) 2_655 ?
 
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
O1A Na1 O1B 159.82(9) 4_565 2_645 ?
O1A Na1 O1B 101.32(8) 4_565 . ?
O1B Na1 O1B 93.58(6) 2_645 . ?
O1A Na1 O1C 77.35(8) 4_565 4 ?
O1B Na1 O1C 92.27(8) 2_645 4 ?
O1B Na1 O1C 163.01(8) . 4 ?
O1A Na1 O1C 82.52(8) 4_565 2_655 ?
O1B Na1 O1C 82.21(8) 2_645 2_655 ?
O1B Na1 O1C 97.07(8) . 2_655 ?
O1C Na1 O1C 99.52(7) 4 2_655 ?
O1A Na1 N2 105.99(9) 4_565 . ?
O1B Na1 N2 89.99(8) 2_645 . ?
O1B Na1 N2 79.27(8) . . ?
O1C Na1 N2 84.80(8) 4 . ?
O1C Na1 N2 171.19(9) 2_655 . ?
O1A Na1 Na1 74.34(6) 4_565 3_655 ?
O1B Na1 Na1 85.71(6) 2_645 3_655 ?
O1B Na1 Na1 146.36(8) . 3_655 ?
O1C Na1 Na1 50.07(6) 4 3_655 ?
O1C Na1 Na1 49.45(5) 2_655 3_655 ?
N2 Na1 Na1 134.31(8) . 3_655 ?
O1A Na1 S1 138.91(7) 4_565 2_645 ?
O1B Na1 S1 22.08(5) 2_645 2_645 ?
O1B Na1 S1 114.76(6) . 2_645 ?
O1C Na1 S1 73.60(6) 4 2_645 ?
O1C Na1 S1 74.44(6) 2_655 2_645 ?
N2 Na1 S1 99.68(7) . 2_645 ?
Na1 Na1 S1 64.78(4) 3_655 2_645 ?
O1A Na1 Na1 97.42(5) 4_565 2_655 ?
O1B Na1 Na1 88.04(6) 2_645 2_655 ?
O1B Na1 Na1 31.91(5) . 2_655 ?
O1C Na1 Na1 164.53(7) 4 2_655 ?
O1C Na1 Na1 65.19(5) 2_655 2_655 ?
N2 Na1 Na1 110.67(7) . 2_655 ?
Na1 Na1 Na1 114.60(5) 3_655 2_655 ?
S1 Na1 Na1 102.89(4) 2_645 2_655 ?
O1A Na1 Na1 166.73(7) 4_565 2_645 ?
O1B Na1 Na1 32.87(5) 2_645 2_645 ?
O1B Na1 Na1 66.41(6) . 2_645 ?
O1C Na1 Na1 112.77(5) 4 2_645 ?
O1C Na1 Na1 103.39(7) 2_655 2_645 ?
N2 Na1 Na1 67.81(6) . 2_645 ?
Na1 Na1 Na1 118.58(6) 3_655 2_645 ?
S1 Na1 Na1 54.29(2) 2_645 2_645 ?
Na1 Na1 Na1 74.93(4) 2_655 2_645 ?
C6 C1 C2 120.8(3) . . ?
C6 C1 S1 119.4(2) . . ?
C2 C1 S1 119.6(2) . . ?
N2 C2 C3 121.2(3) . . ?
N2 C2 C1 120.9(3) . . ?
C3 C2 C1 117.8(3) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C2 N2 Na1 108.71(18) . . ?
C2 N2 H1 120.0 . . ?
Na1 N2 H1 97.3 . . ?
C2 N2 H2 120.0 . . ?
Na1 N2 H2 63.4 . . ?
H1 N2 H2 120.0 . . ?
S1 O1A Na1 140.01(13) . 4_566 ?
S1 O1B Na1 120.70(11) . 2_655 ?
S1 O1B Na1 121.64(11) . . ?
Na1 O1B Na1 115.22(8) 2_655 . ?
S1 O1C Na1 131.56(12) . 4_556 ?
S1 O1C Na1 134.85(12) . 2_645 ?
Na1 O1C Na1 80.48(7) 4_556 2_645 ?
O1A S1 O1C 113.17(12) . . ?
O1A S1 O1B 112.93(12) . . ?
O1C S1 O1B 111.51(12) . . ?
O1A S1 C1 105.55(13) . . ?
O1C S1 C1 107.60(13) . . ?
O1B S1 C1 105.44(12) . . ?
O1A S1 Na1 79.61(9) . 2_655 ?
O1C S1 Na1 113.20(9) . 2_655 ?
O1B S1 Na1 37.23(8) . 2_655 ?
C1 S1 Na1 132.70(10) . 2_655 ?
 
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
N2 H2 O1C  0.88 2.27 2.906(3) 129.0 .
N2 H1 O1A  0.88 2.13 2.912(3) 148.3 4
N2 H1 S1  0.88 2.88 3.628(2) 143.4 4
 
_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.557
_refine_diff_density_min   -0.439
_refine_diff_density_rms    0.087
