 
data_99scw111
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 Benzenrsulfonamido-5-methylpyridine 
; 
_chemical_name_common             Benzenesulfonamido-5-methylpyridine 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C12 H12 N2 O2 S' 
_chemical_formula_weight          248.30 
 
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    P2(1)/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                    11.754(2) 
_cell_length_b                    13.880(3) 
_cell_length_c                    7.2050(10) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  107.18(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1123.0(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       1.81
_cell_measurement_theta_max       25.04
 
_exptl_crystal_description        Triangular 
_exptl_crystal_colour             Colourless 
_exptl_crystal_size_max           0.25 
_exptl_crystal_size_mid           0.12
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.469 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              520 
_exptl_absorpt_coefficient_mu     0.278 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.961
_exptl_absorpt_correction_T_max   0.986
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Nonius KappaCCD'
_diffrn_measurement_method        'φ and 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             8518 
_diffrn_reflns_av_R_equivalents   0.0671 
_diffrn_reflns_av_sigmaI/netI     0.0499 
_diffrn_reflns_limit_h_min        -13 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -16 
_diffrn_reflns_limit_k_max        16 
_diffrn_reflns_limit_l_min        -8 
_diffrn_reflns_limit_l_max        8 
_diffrn_reflns_theta_min          1.81 
_diffrn_reflns_theta_max          25.04 
_reflns_number_total              1983 
_reflns_number_gt                 1596 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection      
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO & COLLECT'
_computing_data_reduction         'DENZO & COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Ortep and Platon' 
_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 w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.1127P] where P=(Fo^2^+2Fc^2^)/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          1983 
_refine_ls_number_parameters      202 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0527 
_refine_ls_R_factor_gt            0.0396 
_refine_ls_wR_factor_ref          0.1080 
_refine_ls_wR_factor_gt           0.1011 
_refine_ls_goodness_of_fit_ref    1.075 
_refine_ls_restrained_S_all       1.075 
_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_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
S1 S 0.23319(4) 0.02773(4) 0.00906(7) 0.0221(2) Uani 1 d . . . 
O1 O 0.21904(12) -0.07562(10) -0.0036(2) 0.0284(4) Uani 1 d . . . 
O2 O 0.21808(12) 0.07274(11) 0.17972(19) 0.0293(4) Uani 1 d . . . 
N1 N 0.36209(14) 0.04621(12) -0.0160(2) 0.0236(4) Uani 1 d . . . 
N2 N 0.52131(14) 0.13905(13) -0.0194(2) 0.0207(4) Uani 1 d . . . 
C1 C -0.0504(2) 0.14997(17) -0.5049(3) 0.0315(5) Uani 1 d . . . 
C2 C 0.0561(2) 0.11936(17) -0.5299(3) 0.0312(5) Uani 1 d . . . 
C3 C 0.14408(19) 0.08236(16) -0.3740(3) 0.0263(5) Uani 1 d . . . 
C4 C 0.12572(17) 0.07880(14) -0.1928(3) 0.0205(5) Uani 1 d . . . 
C5 C 0.01948(17) 0.11034(16) -0.1664(3) 0.0261(5) Uani 1 d . . . 
C6 C -0.06894(19) 0.14529(17) -0.3251(3) 0.0308(5) Uani 1 d . . . 
C7 C 0.40682(16) 0.13647(15) -0.0140(3) 0.0204(4) Uani 1 d . . . 
C8 C 0.35225(18) 0.22679(15) -0.0100(3) 0.0224(5) Uani 1 d . . . 
C9 C 0.41315(18) 0.30988(16) -0.0164(3) 0.0226(5) Uani 1 d . . . 
C10 C 0.53161(18) 0.30966(15) -0.0261(3) 0.0218(5) Uani 1 d . . . 
C11 C 0.58225(18) 0.22150(15) -0.0253(3) 0.0223(5) Uani 1 d . . . 
C12 C 0.5979(2) 0.40051(17) -0.0355(3) 0.0285(5) Uani 1 d . . . 
H1 H -0.1118(19) 0.1764(16) -0.617(3) 0.027(6) Uiso 1 d . . . 
H2A H 0.559(2) 0.079(2) -0.012(3) 0.038(7) Uiso 1 d . . . 
H2 H 0.069(2) 0.1198(18) -0.656(4) 0.042(7) Uiso 1 d . . . 
H3 H 0.214(2) 0.0596(16) -0.393(3) 0.027(6) Uiso 1 d . . . 
H5 H 0.0078(17) 0.1070(16) -0.040(3) 0.026(5) Uiso 1 d . . . 
H6 H -0.144(2) 0.1697(18) -0.306(3) 0.039(6) Uiso 1 d . . . 
H8 H 0.2706(19) 0.2280(16) -0.004(3) 0.025(6) Uiso 1 d . . . 
H9 H 0.3772(19) 0.3692(18) -0.012(3) 0.028(6) Uiso 1 d . . . 
H11 H 0.659(2) 0.2128(16) -0.032(3) 0.028(6) Uiso 1 d . . . 
H12 H 0.620(2) 0.4349(19) 0.089(4) 0.039(6) Uiso 1 d . . . 
H13 H 0.668(2) 0.388(2) -0.077(4) 0.053(8) Uiso 1 d . . . 
H14 H 0.550(2) 0.450(2) -0.128(4) 0.040(7) Uiso 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 
S1 0.0186(3) 0.0228(3) 0.0253(3) 0.0025(2) 0.0070(2) 0.0015(2) 
O1 0.0232(8) 0.0211(9) 0.0410(9) 0.0064(6) 0.0097(7) -0.0003(6) 
O2 0.0259(8) 0.0399(10) 0.0223(8) 0.0001(6) 0.0076(6) 0.0017(7) 
N1 0.0190(9) 0.0207(9) 0.0310(10) 0.0013(7) 0.0072(7) 0.0016(7) 
N2 0.0196(9) 0.0190(10) 0.0233(9) 0.0005(7) 0.0060(7) 0.0018(7) 
C1 0.0300(12) 0.0301(13) 0.0280(12) 0.0035(10) -0.0011(10) -0.0016(10) 
C2 0.0359(13) 0.0348(14) 0.0238(12) 0.0027(9) 0.0103(10) -0.0035(10) 
C3 0.0253(11) 0.0277(13) 0.0282(12) -0.0008(9) 0.0115(9) -0.0004(10) 
C4 0.0198(10) 0.0182(11) 0.0233(11) -0.0012(8) 0.0059(8) -0.0008(8) 
C5 0.0227(11) 0.0290(13) 0.0272(12) -0.0024(9) 0.0084(9) 0.0025(9) 
C6 0.0233(12) 0.0325(14) 0.0338(13) -0.0023(10) 0.0040(9) 0.0042(10) 
C7 0.0182(10) 0.0233(12) 0.0190(10) 0.0018(8) 0.0043(8) 0.0020(8) 
C8 0.0200(10) 0.0268(12) 0.0197(10) 0.0002(8) 0.0049(8) 0.0032(9) 
C9 0.0248(11) 0.0230(12) 0.0178(10) -0.0014(8) 0.0028(8) 0.0041(10) 
C10 0.0247(11) 0.0227(12) 0.0153(10) -0.0006(8) 0.0020(8) -0.0006(9) 
C11 0.0183(11) 0.0253(12) 0.0220(10) -0.0006(8) 0.0039(8) -0.0012(9) 
C12 0.0281(12) 0.0245(13) 0.0300(13) -0.0018(10) 0.0040(10) -0.0027(10) 
 
_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 
S1 O2 1.4362(15) . ? 
S1 O1 1.4439(16) . ? 
S1 N1 1.5986(17) . ? 
S1 C4 1.769(2) . ? 
N1 C7 1.357(3) . ? 
N2 C11 1.357(3) . ? 
N2 C7 1.358(2) . ? 
C1 C6 1.377(3) . ? 
C1 C2 1.383(3) . ? 
C2 C3 1.381(3) . ? 
C3 C4 1.386(3) . ? 
C4 C5 1.388(3) . ? 
C5 C6 1.386(3) . ? 
C7 C8 1.412(3) . ? 
C8 C9 1.365(3) . ? 
C9 C10 1.415(3) . ? 
C10 C11 1.360(3) . ? 
C10 C12 1.494(3) . ? 
 
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 
O2 S1 O1 116.44(8) . . ? 
O2 S1 N1 112.81(9) . . ? 
O1 S1 N1 104.34(9) . . ? 
O2 S1 C4 106.90(9) . . ? 
O1 S1 C4 107.77(9) . . ? 
N1 S1 C4 108.27(9) . . ? 
C7 N1 S1 121.62(14) . . ? 
C11 N2 C7 124.03(18) . . ? 
C6 C1 C2 120.6(2) . . ? 
C3 C2 C1 119.8(2) . . ? 
C2 C3 C4 119.5(2) . . ? 
C3 C4 C5 120.94(19) . . ? 
C3 C4 S1 121.13(15) . . ? 
C5 C4 S1 117.83(15) . . ? 
C6 C5 C4 118.9(2) . . ? 
C1 C6 C5 120.3(2) . . ? 
N1 C7 N2 114.09(17) . . ? 
N1 C7 C8 129.99(18) . . ? 
N2 C7 C8 115.92(18) . . ? 
C9 C8 C7 120.21(19) . . ? 
C8 C9 C10 122.2(2) . . ? 
C11 C10 C9 115.96(19) . . ? 
C11 C10 C12 121.75(19) . . ? 
C9 C10 C12 122.29(19) . . ? 
N2 C11 C10 121.63(19) . . ? 
 
_diffrn_measured_fraction_theta_max    0.955 
_diffrn_reflns_theta_full              25.04 
_diffrn_measured_fraction_theta_full   0.955 
_refine_diff_density_max    0.244 
_refine_diff_density_min   -0.551 
_refine_diff_density_rms    0.070 
