 
data_99scw115
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 p-aminobenzenesulfonamido-5-bromopyridine 
; 
_chemical_name_common             p-aminobenzenesulfonamido-5-bromopyridine 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C11 H10 Br N3 O2 S' 
_chemical_formula_weight          328.19 
 
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' 
 'Br'  'Br'  -0.2901   2.4595 
 '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                    9.933(2) 
_cell_length_b                    11.528(2) 
_cell_length_c                    12.703(3) 
_cell_angle_alpha                 115.74(3) 
_cell_angle_beta                  100.11(3) 
_cell_angle_gamma                 95.54(3) 
_cell_volume                      1265.2(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature    150(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       2.12 
_cell_measurement_theta_max       25.07
 
_exptl_crystal_description        Rods 
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.25 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.05 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.723 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              656 
_exptl_absorpt_coefficient_mu     3.411 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.671
_exptl_absorpt_correction_T_max   0.843
 
_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   20s 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             15587 
_diffrn_reflns_av_R_equivalents   0.0747 
_diffrn_reflns_av_sigmaI/netI     0.0671 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          2.12 
_diffrn_reflns_theta_max          25.07 
_reflns_number_total              4468 
_reflns_number_gt                 3325 
_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^)+(0.0497P)^2^+0.0000P] 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          4468 
_refine_ls_number_parameters      405 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0665 
_refine_ls_R_factor_gt            0.0416 
_refine_ls_wR_factor_ref          0.1050 
_refine_ls_wR_factor_gt           0.0935 
_refine_ls_goodness_of_fit_ref    1.033 
_refine_ls_restrained_S_all       1.033 
_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 
Br1 Br 0.59401(4) 0.22560(5) 0.10565(4) 0.04164(16) Uani 1 d . . . 
S1 S -0.06856(10) -0.11714(11) -0.30521(10) 0.0312(3) Uani 1 d . . . 
O1 O -0.2030(3) -0.1838(3) -0.3113(3) 0.0383(7) Uani 1 d . . . 
O2 O -0.0660(3) -0.0252(3) -0.3529(3) 0.0383(7) Uani 1 d . . . 
N1 N 0.2800(4) -0.4917(4) -0.5351(4) 0.0374(9) Uani 1 d . . . 
N2 N 0.0052(4) -0.0455(4) -0.1621(4) 0.0334(9) Uani 1 d . . . 
N3 N 0.1783(3) 0.0613(3) 0.0113(3) 0.0309(8) Uani 1 d . . . 
C1 C 0.1942(4) -0.4107(4) -0.4864(4) 0.0287(9) Uani 1 d . . . 
C2 C 0.1523(4) -0.4032(4) -0.3833(4) 0.0288(9) Uani 1 d . . . 
C3 C 0.0720(4) -0.3156(4) -0.3290(4) 0.0295(9) Uani 1 d . . . 
C4 C 0.0313(4) -0.2303(4) -0.3743(4) 0.0268(9) Uani 1 d . . . 
C5 C 0.0689(4) -0.2378(4) -0.4774(4) 0.0271(9) Uani 1 d . . . 
C6 C 0.1470(4) -0.3277(4) -0.5330(4) 0.0294(9) Uani 1 d . . . 
C7 C 0.1425(4) 0.0232(4) -0.1058(4) 0.0276(9) Uani 1 d . . . 
C8 C 0.2335(4) 0.0479(4) -0.1680(4) 0.0327(10) Uani 1 d . . . 
C9 C 0.3683(4) 0.1096(4) -0.1067(4) 0.0336(10) Uani 1 d . . . 
C10 C 0.4087(4) 0.1457(4) 0.0153(4) 0.0309(9) Uani 1 d . . . 
C11 C 0.3108(4) 0.1232(4) 0.0719(4) 0.0324(10) Uani 1 d . . . 
H1A H 0.307(5) -0.551(5) -0.508(4) 0.050(14) Uiso 1 d . . . 
H1B H 0.289(5) -0.504(5) -0.610(5) 0.049(14) Uiso 1 d . . . 
H2A H -0.032(5) -0.054(4) -0.129(4) 0.023(14) Uiso 1 d . . . 
H2 H 0.186(4) -0.453(4) -0.351(4) 0.028(11) Uiso 1 d . . . 
H3 H 0.044(4) -0.314(4) -0.263(3) 0.020(10) Uiso 1 d . . . 
H5 H 0.044(4) -0.184(4) -0.509(3) 0.018(10) Uiso 1 d . . . 
H6 H 0.177(4) -0.336(4) -0.604(4) 0.032(11) Uiso 1 d . . . 
H8 H 0.208(4) 0.019(4) -0.251(4) 0.021(10) Uiso 1 d . . . 
H9 H 0.436(5) 0.134(5) -0.144(5) 0.058(14) Uiso 1 d . . . 
H11 H 0.333(4) 0.148(4) 0.161(4) 0.037(12) Uiso 1 d . . . 
Br21 Br 0.92850(4) 0.29196(5) -0.00636(4) 0.03987(16) Uani 1 d . . . 
S21 S 1.46049(11) 0.37314(10) -0.29748(9) 0.0293(2) Uani 1 d . . . 
O21 O 1.5946(3) 0.4483(3) -0.2782(3) 0.0348(7) Uani 1 d . . . 
O22 O 1.3457(3) 0.3660(3) -0.3874(3) 0.0344(7) Uani 1 d . . . 
N21 N 1.5086(5) -0.1632(4) -0.3799(4) 0.0354(9) Uani 1 d . . . 
N22 N 1.4225(4) 0.4419(4) -0.1667(3) 0.0291(8) Uani 1 d . . . 
N23 N 1.3179(3) 0.4324(3) -0.0213(3) 0.0294(8) Uani 1 d . . . 
C21 C 1.5000(4) -0.0390(4) -0.3635(4) 0.0287(9) Uani 1 d . . . 
C22 C 1.6108(4) 0.0658(4) -0.2912(4) 0.0287(9) Uani 1 d . . . 
C23 C 1.5990(4) 0.1911(4) -0.2721(4) 0.0291(9) Uani 1 d . . . 
C24 C 1.4765(4) 0.2140(4) -0.3265(3) 0.0270(9) Uani 1 d . . . 
C25 C 1.3667(4) 0.1099(4) -0.4012(4) 0.0277(9) Uani 1 d . . . 
C26 C 1.3776(4) -0.0153(4) -0.4190(4) 0.0283(9) Uani 1 d . . . 
C27 C 1.3017(4) 0.4012(4) -0.1382(4) 0.0289(9) Uani 1 d . . . 
C28 C 1.1746(4) 0.3352(4) -0.2233(4) 0.0344(10) Uani 1 d . . . 
C29 C 1.0629(5) 0.3016(4) -0.1849(4) 0.0332(10) Uani 1 d . . . 
C210 C 1.0796(4) 0.3345(4) -0.0645(4) 0.0324(10) Uani 1 d . . . 
C211 C 1.2073(4) 0.4007(4) 0.0150(4) 0.0312(9) Uani 1 d . . . 
H21A H 1.589(5) -0.182(4) -0.366(4) 0.026(11) Uiso 1 d . . . 
H21B H 1.443(5) -0.225(5) -0.423(4) 0.037(14) Uiso 1 d . . . 
H22A H 1.486(4) 0.479(4) -0.113(4) 0.018(11) Uiso 1 d . . . 
H22 H 1.697(4) 0.058(4) -0.250(3) 0.025(10) Uiso 1 d . . . 
H23 H 1.669(4) 0.259(4) -0.227(3) 0.013(9) Uiso 1 d . . . 
H25 H 1.279(4) 0.122(4) -0.444(4) 0.035(11) Uiso 1 d . . . 
H26 H 1.306(4) -0.087(4) -0.472(4) 0.031(11) Uiso 1 d . . . 
H28 H 1.178(5) 0.324(5) -0.299(5) 0.048(14) Uiso 1 d . . . 
H29 H 0.975(5) 0.250(4) -0.241(4) 0.040(12) Uiso 1 d . . . 
H211 H 1.232(4) 0.431(4) 0.113(4) 0.023(10) 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 
Br1 C10 1.889(4) . ? 
S1 O2 1.431(3) . ? 
S1 O1 1.447(3) . ? 
S1 N2 1.623(4) . ? 
S1 C4 1.737(4) . ? 
N1 C1 1.348(5) . ? 
N2 C7 1.399(6) . ? 
N3 C7 1.323(5) . ? 
N3 C11 1.349(5) . ? 
C1 C6 1.402(5) . ? 
C1 C2 1.414(6) . ? 
C2 C3 1.369(6) . ? 
C3 C4 1.396(5) . ? 
C4 C5 1.393(5) . ? 
C5 C6 1.374(6) . ? 
C7 C8 1.385(6) . ? 
C8 C9 1.368(6) . ? 
C9 C10 1.388(6) . ? 
C10 C11 1.373(6) . ? 
Br21 C210 1.898(4) . ? 
S21 O22 1.433(3) . ? 
S21 O21 1.437(3) . ? 
S21 N22 1.632(4) . ? 
S21 C24 1.737(4) . ? 
N21 C21 1.369(5) . ? 
N22 C27 1.408(5) . ? 
N23 C211 1.342(5) . ? 
N23 C27 1.342(5) . ? 
C21 C22 1.393(6) . ? 
C21 C26 1.407(5) . ? 
C22 C23 1.377(6) . ? 
C23 C24 1.398(5) . ? 
C24 C25 1.387(6) . ? 
C25 C26 1.378(6) . ? 
C27 C28 1.401(6) . ? 
C28 C29 1.375(6) . ? 
C29 C210 1.380(6) . ? 
C210 C211 1.380(6) . ? 
 
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 117.96(17) . . ? 
O2 S1 N2 111.0(2) . . ? 
O1 S1 N2 102.9(2) . . ? 
O2 S1 C4 107.66(18) . . ? 
O1 S1 C4 110.43(18) . . ? 
N2 S1 C4 106.30(19) . . ? 
C7 N2 S1 127.4(3) . . ? 
C7 N3 C11 118.3(4) . . ? 
N1 C1 C6 121.7(4) . . ? 
N1 C1 C2 120.8(4) . . ? 
C6 C1 C2 117.4(4) . . ? 
C3 C2 C1 121.2(4) . . ? 
C2 C3 C4 120.2(4) . . ? 
C5 C4 C3 119.6(4) . . ? 
C5 C4 S1 119.7(3) . . ? 
C3 C4 S1 120.7(3) . . ? 
C6 C5 C4 120.0(4) . . ? 
C5 C6 C1 121.5(4) . . ? 
N3 C7 C8 123.0(4) . . ? 
N3 C7 N2 114.4(4) . . ? 
C8 C7 N2 122.7(4) . . ? 
C9 C8 C7 118.6(4) . . ? 
C8 C9 C10 119.0(4) . . ? 
C11 C10 C9 119.0(4) . . ? 
C11 C10 Br1 119.2(3) . . ? 
C9 C10 Br1 121.8(3) . . ? 
N3 C11 C10 122.0(4) . . ? 
O22 S21 O21 119.33(16) . . ? 
O22 S21 N22 108.41(18) . . ? 
O21 S21 N22 103.88(19) . . ? 
O22 S21 C24 108.13(19) . . ? 
O21 S21 C24 109.47(18) . . ? 
N22 S21 C24 106.95(18) . . ? 
C27 N22 S21 125.8(3) . . ? 
C211 N23 C27 118.4(4) . . ? 
N21 C21 C22 120.8(4) . . ? 
N21 C21 C26 120.2(4) . . ? 
C22 C21 C26 119.0(4) . . ? 
C23 C22 C21 120.3(4) . . ? 
C22 C23 C24 120.3(4) . . ? 
C25 C24 C23 119.9(4) . . ? 
C25 C24 S21 120.2(3) . . ? 
C23 C24 S21 119.9(3) . . ? 
C26 C25 C24 119.8(4) . . ? 
C25 C26 C21 120.6(4) . . ? 
N23 C27 C28 122.4(4) . . ? 
N23 C27 N22 114.2(4) . . ? 
C28 C27 N22 123.4(4) . . ? 
C29 C28 C27 118.4(4) . . ? 
C28 C29 C210 119.1(4) . . ? 
C211 C210 C29 119.7(4) . . ? 
C211 C210 Br21 119.5(3) . . ? 
C29 C210 Br21 120.8(3) . . ? 
N23 C211 C210 122.0(4) . . ? 
 
_diffrn_measured_fraction_theta_max    0.994 
_diffrn_reflns_theta_full              25.07 
_diffrn_measured_fraction_theta_full   0.994 
_refine_diff_density_max    0.404 
_refine_diff_density_min   -0.716 
_refine_diff_density_rms    0.099 
