#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/92/1519227.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_1519227
loop_
_publ_author_name
'Threlfall, Terry L.'
'Coles, Simon J.'
'Ward, Suzanna C.'
'Hursthouse, Michael B.'
_publ_section_title
;
 p-acetoamidobenzenesulfonamide-5-chloropyridine
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              164
_journal_year                    1999
_chemical_formula_sum            'C13 H12 Cl N3 O3 S'
_chemical_formula_weight         325.77
_chemical_name_common            p-acetoamidobenzenesulfonamido-5-chloropyridine
_chemical_name_systematic
; 
p-acetoamidobenzenesulfonamido-5-chloropyridine 
;
_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                90.01(3)
_cell_angle_beta                 108.24(3)
_cell_angle_gamma                103.77(3)
_cell_formula_units_Z            2
_cell_length_a                   7.879(2)
_cell_length_b                   9.393(2)
_cell_length_c                   10.085(2)
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.13
_cell_volume                     686.2(3)
_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  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8309
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.444
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2415
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0275P)^2^+0.4581P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0806
_reflns_number_gt                2240
_reflns_number_total             2415
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-164.cif
_cod_data_source_block           99scw114
_cod_depositor_comments
;
Citation :
Threlfall, Terry L and Coles, Simon J. and Ward, Suzanna C and 
Hursthouse, Michael B. (1999) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/164)

More at:
http://ecrystals.chem.soton.ac.uk/164/

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_sg_symbol_H-M      P-1
_cod_database_code               1519227
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
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 . . .
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'
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
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) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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) .
