#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/92/1519229.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1519229
loop_
_publ_author_name
'Threlfall, Terry L.'
'Coles, Simon J.'
'Hursthouse, Michael B.'
'Ward, Suzanna C.'
_publ_section_title
;
 p-aminobenzenesulfonamide-5-bromopyridine
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              174
_journal_year                    1999
_chemical_formula_sum            'C11 H10 Br N3 O2 S'
_chemical_formula_weight         328.19
_chemical_name_common            p-aminobenzenesulfonamido-5-bromopyridine
_chemical_name_systematic
; 
 p-aminobenzenesulfonamido-5-bromopyridine 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                115.74(3)
_cell_angle_beta                 100.11(3)
_cell_angle_gamma                95.54(3)
_cell_formula_units_Z            4
_cell_length_a                   9.933(2)
_cell_length_b                   11.528(2)
_cell_length_c                   12.703(3)
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.07
_cell_measurement_theta_min      2.12
_cell_volume                     1265.2(6)
_computing_cell_refinement       'DENZO & COLLECT'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO & COLLECT'
_computing_molecular_graphics    'Ortep and Platon'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_sigmaI/netI    0.0671
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15587
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    3.411
_exptl_absorpt_correction_T_max  0.843
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rods
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         4468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1050
_reflns_number_gt                3325
_reflns_number_total             4468
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-174.cif
_cod_data_source_block           99scw115
_cod_depositor_comments
;
Citation :
Threlfall, Terry L and Coles, Simon J. and Hursthouse, Michael B. and 
Ward, Suzanna C (1999) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/174)

More at:
http://ecrystals.chem.soton.ac.uk/174/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3105 2015-03-04 15:46:00Z robertas 
;
_cod_original_cell_volume        1265.2(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1519229
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 . . .
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'
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
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) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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) .
