 
data_99scw114
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
p-acetoamidobenzenesulfonamido-5-chloropyridine 
; 
_chemical_name_common             
p-acetoamidobenzenesulfonamido-5-chloropyridine 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C13 H12 Cl N3 O3 S' 
_chemical_formula_weight          325.77 
 
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                    7.879(2) 
_cell_length_b                    9.393(2) 
_cell_length_c                    10.085(2) 
_cell_angle_alpha                 90.01(3) 
_cell_angle_beta                  108.24(3) 
_cell_angle_gamma                 103.77(3) 
_cell_volume                      686.2(3) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       2.13
_cell_measurement_theta_max       24.99
 
_exptl_crystal_description        Block 
_exptl_crystal_colour             Colourless 
_exptl_crystal_size_max           0.30 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.15 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.577 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              336 
_exptl_absorpt_coefficient_mu     0.444 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.899
_exptl_absorpt_correction_T_max   0.936
 
_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             8309 
_diffrn_reflns_av_R_equivalents   0.0404 
_diffrn_reflns_av_sigmaI/netI     0.0344 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -11 
_diffrn_reflns_limit_l_max        11 
_diffrn_reflns_theta_min          2.13 
_diffrn_reflns_theta_max          24.99 
_reflns_number_total              2415 
_reflns_number_gt                 2240 
_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^)+(0.0275P)^2^+0.4581P] 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          2415 
_refine_ls_number_parameters      238 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0340 
_refine_ls_R_factor_gt            0.0313 
_refine_ls_wR_factor_ref          0.0806 
_refine_ls_wR_factor_gt           0.0782 
_refine_ls_goodness_of_fit_ref    1.111 
_refine_ls_restrained_S_all       1.111 
_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_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
Cl1 Cl 0.88284(7) 0.78609(5) 0.87616(5) 0.02934(15) Uani 1 d . . . 
S1 S 0.50478(5) 0.03384(5) 0.77324(4) 0.01589(14) Uani 1 d . . . 
O1 O 0.59593(16) 0.02968(14) 0.67199(12) 0.0204(3) Uani 1 d . . . 
O2 O 0.45651(17) -0.09752(13) 0.84142(13) 0.0210(3) Uani 1 d . . . 
O3 O -0.10151(18) 0.38464(16) 0.35352(14) 0.0283(3) Uani 1 d . . . 
N1 N -0.1606(2) 0.25735(17) 0.53337(16) 0.0193(3) Uani 1 d . . . 
N2 N 0.6375(2) 0.15327(16) 0.90559(16) 0.0180(3) Uani 1 d . . . 
N3 N 0.7189(2) 0.35464(17) 0.78035(15) 0.0201(3) Uani 1 d . . . 
C1 C -0.3787(3) 0.3882(2) 0.4000(2) 0.0260(4) Uani 1 d . . . 
C2 C -0.2001(2) 0.3451(2) 0.42554(18) 0.0196(4) Uani 1 d . . . 
C3 C -0.0025(2) 0.20379(18) 0.58397(17) 0.0168(4) Uani 1 d . . . 
C4 C 0.1117(2) 0.1932(2) 0.50475(19) 0.0186(4) Uani 1 d . . . 
C5 C 0.2659(2) 0.13978(19) 0.56191(18) 0.0178(4) Uani 1 d . . . 
C6 C 0.3066(2) 0.09707(18) 0.69728(17) 0.0159(4) Uani 1 d . . . 
C7 C 0.1910(2) 0.1033(2) 0.77621(18) 0.0190(4) Uani 1 d . . . 
C8 C 0.0368(2) 0.1556(2) 0.71883(18) 0.0183(4) Uani 1 d . . . 
C9 C 0.6921(2) 0.30641(19) 0.89752(17) 0.0167(4) Uani 1 d . . . 
C10 C 0.7204(3) 0.3973(2) 1.0155(2) 0.0254(4) Uani 1 d . . . 
C11 C 0.7795(3) 0.5465(2) 1.0103(2) 0.0270(4) Uani 1 d . . . 
C12 C 0.8077(2) 0.5989(2) 0.88901(19) 0.0204(4) Uani 1 d . . . 
C13 C 0.7779(2) 0.5012(2) 0.7774(2) 0.0213(4) Uani 1 d . . . 
H1A H -0.227(3) 0.245(2) 0.586(2) 0.030(6) Uiso 1 d . . . 
H1B H -0.428(3) 0.375(3) 0.478(3) 0.043(7) Uiso 1 d . . . 
H1C H -0.468(4) 0.334(3) 0.318(3) 0.050(7) Uiso 1 d . . . 
H1D H -0.364(4) 0.485(3) 0.375(3) 0.057(8) Uiso 1 d . . . 
H2A H 0.614(3) 0.130(3) 0.982(3) 0.032(6) Uiso 1 d . . . 
H4 H 0.085(3) 0.222(2) 0.414(2) 0.027(5) Uiso 1 d . . . 
H5 H 0.337(3) 0.131(2) 0.506(2) 0.019(5) Uiso 1 d . . . 
H7 H 0.219(3) 0.075(2) 0.870(2) 0.028(5) Uiso 1 d . . . 
H8 H -0.041(3) 0.159(2) 0.770(2) 0.022(5) Uiso 1 d . . . 
H10 H 0.701(3) 0.357(2) 1.096(2) 0.028(5) Uiso 1 d . . . 
H11 H 0.800(3) 0.613(3) 1.090(3) 0.044(7) Uiso 1 d . . . 
H13 H 0.796(3) 0.533(2) 0.693(2) 0.024(5) 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 
Cl1 C12 1.7357(19) . ? 
S1 O1 1.4256(13) . ? 
S1 O2 1.4425(13) . ? 
S1 N2 1.6434(17) . ? 
S1 C6 1.7526(17) . ? 
O3 C2 1.219(2) . ? 
N1 C2 1.368(2) . ? 
N1 C3 1.402(2) . ? 
N2 C9 1.410(2) . ? 
N3 C9 1.326(2) . ? 
N3 C13 1.348(2) . ? 
C1 C2 1.501(3) . ? 
C3 C4 1.396(2) . ? 
C3 C8 1.398(3) . ? 
C4 C5 1.383(3) . ? 
C5 C6 1.384(2) . ? 
C6 C7 1.395(2) . ? 
C7 C8 1.377(3) . ? 
C9 C10 1.392(3) . ? 
C10 C11 1.374(3) . ? 
C11 C12 1.381(3) . ? 
C12 C13 1.377(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 
O1 S1 O2 118.97(8) . . ? 
O1 S1 N2 110.06(8) . . ? 
O2 S1 N2 102.71(8) . . ? 
O1 S1 C6 108.81(8) . . ? 
O2 S1 C6 109.07(8) . . ? 
N2 S1 C6 106.48(8) . . ? 
C2 N1 C3 127.46(15) . . ? 
C9 N2 S1 124.98(12) . . ? 
C9 N3 C13 117.04(16) . . ? 
O3 C2 N1 123.62(16) . . ? 
O3 C2 C1 121.77(17) . . ? 
N1 C2 C1 114.60(16) . . ? 
C4 C3 C8 119.61(16) . . ? 
C4 C3 N1 123.04(16) . . ? 
C8 C3 N1 117.32(15) . . ? 
C5 C4 C3 119.81(16) . . ? 
C4 C5 C6 119.93(16) . . ? 
C5 C6 C7 120.84(16) . . ? 
C5 C6 S1 120.60(13) . . ? 
C7 C6 S1 118.56(13) . . ? 
C8 C7 C6 119.15(16) . . ? 
C7 C8 C3 120.61(16) . . ? 
N3 C9 C10 124.13(17) . . ? 
N3 C9 N2 118.25(16) . . ? 
C10 C9 N2 117.58(16) . . ? 
C11 C10 C9 118.05(18) . . ? 
C10 C11 C12 118.66(18) . . ? 
C13 C12 C11 119.57(17) . . ? 
C13 C12 Cl1 119.58(14) . . ? 
C11 C12 Cl1 120.84(15) . . ? 
N3 C13 C12 122.53(17) . . ? 
 
_diffrn_measured_fraction_theta_max    0.994 
_diffrn_reflns_theta_full              24.99 
_diffrn_measured_fraction_theta_full   0.994 
_refine_diff_density_max    0.236 
_refine_diff_density_min   -0.392 
_refine_diff_density_rms    0.053 
