 
data_99scw106
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 Benzenesulfonamido-5-chloropyridine 
; 
_chemical_name_common             'benzenesulfonamido-5-chloropyridine' 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C11 H9 Cl N2 O2 S' 
_chemical_formula_weight          268.71 
 
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' 
 'Cl'  'Cl'   0.1484   0.1585 
 '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                    9.643(2) 
_cell_length_b                    11.069(2) 
_cell_length_c                    11.162(2) 
_cell_angle_alpha                 93.35(3) 
_cell_angle_beta                  102.12(3) 
_cell_angle_gamma                 98.20(3) 
_cell_volume                      1148.1(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       1.87 
_cell_measurement_theta_max       24.97
 
_exptl_crystal_description        Needles 
_exptl_crystal_colour             Colourless 
_exptl_crystal_size_max           0.35 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.15
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.555 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              552 
_exptl_absorpt_coefficient_mu     0.504 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.927
_exptl_absorpt_correction_T_max   0.941 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(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             14032 
_diffrn_reflns_av_R_equivalents   0.0421 
_diffrn_reflns_av_sigmaI/netI     0.0430 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -13 
_diffrn_reflns_limit_l_max        13 
_diffrn_reflns_theta_min          1.87 
_diffrn_reflns_theta_max          24.97 
_reflns_number_total              4016 
_reflns_number_gt                 3239 
_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^)+(0.0484P)^2^+0.2730P] 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          4016 
_refine_ls_number_parameters      379 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0501 
_refine_ls_R_factor_gt            0.0366 
_refine_ls_wR_factor_ref          0.0933 
_refine_ls_wR_factor_gt           0.0867 
_refine_ls_goodness_of_fit_ref    1.054 
_refine_ls_restrained_S_all       1.054 
_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 -0.00353(5) 0.69594(5) 0.02569(4) 0.02302(15) Uani 1 d . . . 
Cl1 Cl 0.60256(6) 1.15994(6) 0.17130(5) 0.03855(18) Uani 1 d . . . 
O1 O -0.15557(15) 0.67660(14) 0.01661(13) 0.0284(4) Uani 1 d . . . 
O2 O 0.08785(16) 0.63835(14) 0.11473(13) 0.0290(4) Uani 1 d . . . 
N1 N 0.04330(19) 0.84421(17) 0.05353(16) 0.0251(4) Uani 1 d . . . 
N2 N 0.18850(18) 1.02850(16) 0.06011(16) 0.0259(4) Uani 1 d . . . 
C1 C 0.0741(3) 0.5896(2) -0.3479(2) 0.0342(6) Uani 1 d . . . 
C2 C -0.0521(3) 0.6324(2) -0.3390(2) 0.0352(6) Uani 1 d . . . 
C3 C -0.0760(2) 0.6664(2) -0.2248(2) 0.0284(5) Uani 1 d . . . 
C4 C 0.0274(2) 0.65578(19) -0.12043(18) 0.0221(5) Uani 1 d . . . 
C5 C 0.1531(2) 0.6119(2) -0.1286(2) 0.0269(5) Uani 1 d . . . 
C6 C 0.1755(2) 0.5791(2) -0.2441(2) 0.0323(5) Uani 1 d . . . 
C7 C 0.1832(2) 0.9113(2) 0.08309(18) 0.0235(5) Uani 1 d . . . 
C8 C 0.3050(2) 0.8632(2) 0.1357(2) 0.0307(5) Uani 1 d . . . 
C9 C 0.4353(2) 0.9395(2) 0.1633(2) 0.0327(6) Uani 1 d . . . 
C10 C 0.4415(2) 1.0603(2) 0.13934(19) 0.0264(5) Uani 1 d . . . 
C11 C 0.3159(2) 1.1018(2) 0.0883(2) 0.0311(5) Uani 1 d . . . 
H1 H 0.090(2) 0.566(2) -0.423(2) 0.032(6) Uiso 1 d . . . 
H1A H -0.021(3) 0.881(2) 0.020(2) 0.032(7) Uiso 1 d . . . 
H2 H -0.124(3) 0.641(2) -0.413(2) 0.048(7) Uiso 1 d . . . 
H3 H -0.155(3) 0.695(2) -0.217(2) 0.030(6) Uiso 1 d . . . 
H5 H 0.221(2) 0.604(2) -0.055(2) 0.030(6) Uiso 1 d . . . 
H6 H 0.261(3) 0.552(2) -0.247(2) 0.045(7) Uiso 1 d . . . 
H8 H 0.300(2) 0.782(2) 0.154(2) 0.032(6) Uiso 1 d . . . 
H9 H 0.523(3) 0.916(2) 0.202(2) 0.039(7) Uiso 1 d . . . 
H11 H 0.318(3) 1.186(2) 0.075(2) 0.035(6) Uiso 1 d . . . 
S21 S -0.48465(5) 0.30396(5) 0.47900(4) 0.02452(15) Uani 1 d . . . 
Cl21 Cl 0.09712(6) 0.00155(6) 0.71300(6) 0.03907(18) Uani 1 d . . . 
N21 N -0.4355(2) 0.16845(19) 0.48187(16) 0.0255(4) Uani 1 d . . . 
N22 N -0.30680(18) 0.01955(17) 0.55500(15) 0.0267(4) Uani 1 d . . . 
O21 O -0.62259(15) 0.28385(14) 0.39665(13) 0.0302(4) Uani 1 d . . . 
O22 O -0.37060(16) 0.39114(15) 0.45619(13) 0.0315(4) Uani 1 d . . . 
C21 C -0.5387(3) 0.3883(2) 0.8650(2) 0.0325(6) Uani 1 d . . . 
C22 C -0.6408(2) 0.3035(2) 0.7845(2) 0.0312(5) Uani 1 d . . . 
C23 C -0.6257(2) 0.2792(2) 0.6652(2) 0.0281(5) Uani 1 d . . . 
C24 C -0.5074(2) 0.34051(19) 0.62878(18) 0.0225(5) Uani 1 d . . . 
C25 C -0.4057(2) 0.4262(2) 0.7086(2) 0.0272(5) Uani 1 d . . . 
C26 C -0.4221(2) 0.4497(2) 0.8281(2) 0.0315(5) Uani 1 d . . . 
C27 C -0.3030(2) 0.1391(2) 0.54242(18) 0.0236(5) Uani 1 d . . . 
C28 C -0.1797(2) 0.2238(2) 0.5852(2) 0.0305(5) Uani 1 d . . . 
C29 C -0.0549(2) 0.1837(2) 0.6382(2) 0.0326(5) Uani 1 d . . . 
C210 C -0.0569(2) 0.0595(2) 0.64784(19) 0.0276(5) Uani 1 d . . . 
C211 C -0.1842(2) -0.0194(2) 0.6071(2) 0.0291(5) Uani 1 d . . . 
H21 H -0.548(3) 0.401(2) 0.941(2) 0.035(7) Uiso 1 d . . . 
H21A H -0.502(3) 0.116(2) 0.474(2) 0.026(7) Uiso 1 d . . . 
H22 H -0.720(3) 0.259(2) 0.808(2) 0.042(7) Uiso 1 d . . . 
H23 H -0.695(2) 0.222(2) 0.607(2) 0.032(6) Uiso 1 d . . . 
H25 H -0.328(2) 0.467(2) 0.6834(18) 0.022(6) Uiso 1 d . . . 
H26 H -0.349(3) 0.511(2) 0.882(2) 0.037(7) Uiso 1 d . . . 
H28 H -0.181(3) 0.302(3) 0.585(2) 0.040(7) Uiso 1 d . . . 
H29 H 0.031(3) 0.239(2) 0.6678(19) 0.027(6) Uiso 1 d . . . 
H211 H -0.190(2) -0.104(2) 0.6184(19) 0.030(6) Uiso 1 d . . . 
 
 
_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 1.4273(15) . ? 
S1 O1 1.4322(15) . ? 
S1 N1 1.6323(19) . ? 
S1 C4 1.762(2) . ? 
Cl1 C10 1.729(2) . ? 
N1 C7 1.407(3) . ? 
N2 C7 1.333(3) . ? 
N2 C11 1.338(3) . ? 
C1 C6 1.373(3) . ? 
C1 C2 1.387(3) . ? 
C2 C3 1.383(3) . ? 
C3 C4 1.388(3) . ? 
C4 C5 1.387(3) . ? 
C5 C6 1.387(3) . ? 
C7 C8 1.390(3) . ? 
C8 C9 1.376(3) . ? 
C9 C10 1.374(3) . ? 
C10 C11 1.379(3) . ? 
S21 O21 1.4290(15) . ? 
S21 O22 1.4313(17) . ? 
S21 N21 1.637(2) . ? 
S21 C24 1.763(2) . ? 
Cl21 C210 1.737(2) . ? 
N21 C27 1.405(3) . ? 
N22 C27 1.335(3) . ? 
N22 C211 1.345(3) . ? 
C21 C26 1.379(3) . ? 
C21 C22 1.387(3) . ? 
C22 C23 1.384(3) . ? 
C23 C24 1.391(3) . ? 
C24 C25 1.387(3) . ? 
C25 C26 1.390(3) . ? 
C27 C28 1.383(3) . ? 
C28 C29 1.371(3) . ? 
C29 C210 1.382(3) . ? 
C210 C211 1.375(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 120.24(10) . . ? 
O2 S1 N1 108.52(10) . . ? 
O1 S1 N1 104.09(10) . . ? 
O2 S1 C4 108.26(9) . . ? 
O1 S1 C4 107.98(9) . . ? 
N1 S1 C4 107.05(10) . . ? 
C7 N1 S1 127.66(15) . . ? 
C7 N2 C11 118.57(18) . . ? 
C6 C1 C2 120.7(2) . . ? 
C3 C2 C1 120.0(2) . . ? 
C2 C3 C4 118.9(2) . . ? 
C5 C4 C3 121.4(2) . . ? 
C5 C4 S1 119.31(16) . . ? 
C3 C4 S1 119.27(16) . . ? 
C6 C5 C4 118.8(2) . . ? 
C1 C6 C5 120.2(2) . . ? 
N2 C7 C8 122.3(2) . . ? 
N2 C7 N1 113.52(18) . . ? 
C8 C7 N1 124.1(2) . . ? 
C9 C8 C7 118.4(2) . . ? 
C10 C9 C8 119.5(2) . . ? 
C9 C10 C11 118.8(2) . . ? 
C9 C10 Cl1 121.40(17) . . ? 
C11 C10 Cl1 119.82(18) . . ? 
N2 C11 C10 122.4(2) . . ? 
O21 S21 O22 120.43(9) . . ? 
O21 S21 N21 104.25(10) . . ? 
O22 S21 N21 109.19(10) . . ? 
O21 S21 C24 108.44(9) . . ? 
O22 S21 C24 108.38(10) . . ? 
N21 S21 C24 105.08(10) . . ? 
C27 N21 S21 127.30(17) . . ? 
C27 N22 C211 118.2(2) . . ? 
C26 C21 C22 121.1(2) . . ? 
C23 C22 C21 119.7(2) . . ? 
C22 C23 C24 119.0(2) . . ? 
C25 C24 C23 121.5(2) . . ? 
C25 C24 S21 119.79(17) . . ? 
C23 C24 S21 118.68(16) . . ? 
C24 C25 C26 118.9(2) . . ? 
C21 C26 C25 119.8(2) . . ? 
N22 C27 C28 122.46(19) . . ? 
N22 C27 N21 113.22(19) . . ? 
C28 C27 N21 124.3(2) . . ? 
C29 C28 C27 119.1(2) . . ? 
C28 C29 C210 118.8(2) . . ? 
C211 C210 C29 119.2(2) . . ? 
C211 C210 Cl21 119.36(18) . . ? 
C29 C210 Cl21 121.47(18) . . ? 
N22 C211 C210 122.3(2) . . ? 
 
_diffrn_measured_fraction_theta_max    0.995 
_diffrn_reflns_theta_full              24.97 
_diffrn_measured_fraction_theta_full   0.995 
_refine_diff_density_max    0.354 
_refine_diff_density_min   -0.412 
_refine_diff_density_rms    0.059 
