#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/75/2217591.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2217591
loop_
_publ_author_name
'Peng-Wei Zhang'
'Wen-Yuan Gao'
'Li Zhang'
'Shou-Cheng Pu'
_publ_section_title
;
 4-(4-Nitrobenzenesulfonamido)pyridinium trichloroacetate
;
_journal_coeditor_code           NC2087
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o438
_journal_page_last               o438
_journal_paper_doi               10.1107/S160053680800069X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C11 H10 N3 O4 S1, C2 Cl3 O2'
_chemical_formula_moiety         'C11 H10 N3 O4 S1, C2 Cl3 O2'
_chemical_formula_sum            'C13 H10 Cl3 N3 O6 S'
_chemical_formula_weight         442.65
_chemical_name_systematic
;
4-(4-Nitrobenzenesulfonamido)pyridinium trichloroacetate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.48(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.017(4)
_cell_length_b                   6.2187(12)
_cell_length_c                   12.719(3)
_cell_measurement_reflns_used    4622
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.073
_cell_measurement_theta_min      1.756
_cell_volume                     1726.6(6)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      111(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0611
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9585
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  0.9730
_exptl_absorpt_correction_T_min  0.9097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lamellar
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.535
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3017
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0873P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1615
_reflns_number_gt                2440
_reflns_number_total             3017
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2087.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C13 H10 Cl3 N3 O6 S1'
_cod_database_code               2217591
_cod_database_fobs_code          2217591
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.18257(4) 1.36555(14) 0.07245(7) 0.0191(3) Uani d . 1
O O1 0.18542(11) 1.5313(4) 0.1516(2) 0.0249(6) Uani d . 1
O O2 0.16464(11) 1.4166(4) -0.03720(19) 0.0246(6) Uani d . 1
O O3 0.04962(13) 0.5416(5) 0.2777(2) 0.0357(7) Uani d . 1
O O4 -0.00146(13) 0.5394(5) 0.1197(2) 0.0409(8) Uani d . 1
N N1 0.30157(14) 0.6878(5) -0.0407(3) 0.0231(7) Uani d D 1
N N2 0.25080(13) 1.2586(5) 0.0880(2) 0.0193(7) Uani d D 1
N N3 0.03717(14) 0.6156(5) 0.1877(3) 0.0248(7) Uani d . 1
C C1 0.26602(16) 1.0661(5) 0.0425(3) 0.0182(8) Uani d . 1
C C2 0.31203(16) 0.9400(6) 0.0978(3) 0.0219(8) Uani d . 1
H H2A 0.3310 0.9837 0.1639 0.026 Uiso calc R 1
C C3 0.32893(16) 0.7525(6) 0.0544(3) 0.0241(8) Uani d . 1
H H3 0.3597 0.6688 0.0910 0.029 Uiso calc R 1
C C4 0.25743(16) 0.8040(6) -0.0958(3) 0.0225(8) Uani d . 1
H H4 0.2395 0.7554 -0.1618 0.027 Uiso calc R 1
C C5 0.23811(16) 0.9937(6) -0.0568(3) 0.0209(8) Uani d . 1
H H5 0.2071 1.0732 -0.0954 0.025 Uiso calc R 1
C C6 0.13549(15) 1.1534(5) 0.1065(3) 0.0185(8) Uani d . 1
C C7 0.09757(15) 1.0470(6) 0.0274(3) 0.0213(8) Uani d . 1
H H7 0.0944 1.0934 -0.0426 0.026 Uiso calc R 1
C C8 0.06426(16) 0.8695(6) 0.0547(3) 0.0216(8) Uani d . 1
H H8 0.0387 0.7945 0.0034 0.026 Uiso calc R 1
C C9 0.07022(15) 0.8085(6) 0.1592(3) 0.0209(8) Uani d . 1
C C10 0.10690(16) 0.9146(6) 0.2399(3) 0.0219(8) Uani d . 1
H H10 0.1088 0.8706 0.3101 0.026 Uiso calc R 1
C C11 0.14059(16) 1.0888(6) 0.2117(3) 0.0232(8) Uani d . 1
H H11 0.1665 1.1622 0.2632 0.028 Uiso calc R 1
Cl Cl1 0.43685(4) 0.58693(15) 0.39003(8) 0.0283(3) Uani d . 1
Cl Cl2 0.46462(5) 0.17077(17) 0.30622(9) 0.0365(3) Uani d . 1
Cl Cl3 0.41727(4) 0.20184(16) 0.50681(7) 0.0291(3) Uani d . 1
O O5 0.31493(11) 0.1505(4) 0.33912(19) 0.0230(6) Uani d . 1
O O6 0.33887(11) 0.4175(4) 0.2360(2) 0.0265(6) Uani d . 1
C C12 0.41404(16) 0.3150(6) 0.3785(3) 0.0212(8) Uani d . 1
C C13 0.34910(16) 0.2939(5) 0.3118(3) 0.0180(7) Uani d . 1
H H1 0.3107(17) 0.568(4) -0.075(3) 0.028(11) Uiso d D 1
H H2 0.2756(17) 1.324(6) 0.140(3) 0.047(13) Uiso d D 1
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
O2 S1 O1 120.25(15)
O2 S1 N2 109.93(16)
O1 S1 N2 104.59(14)
O2 S1 C6 107.91(16)
O1 S1 C6 109.75(17)
N2 S1 C6 103.08(16)
C4 N1 C3 121.4(3)
C4 N1 H1 113(2)
C3 N1 H1 126(2)
C1 N2 S1 124.7(2)
C1 N2 H2 123(3)
S1 N2 H2 112(3)
O4 N3 O3 124.1(3)
O4 N3 C9 117.4(3)
O3 N3 C9 118.4(3)
N2 C1 C2 118.2(3)
N2 C1 C5 123.4(3)
C2 C1 C5 118.4(3)
C3 C2 C1 119.7(3)
C3 C2 H2A 120.2
C1 C2 H2A 120.2
N1 C3 C2 120.5(3)
N1 C3 H3 119.7
C2 C3 H3 119.7
N1 C4 C5 121.1(3)
N1 C4 H4 119.5
C5 C4 H4 119.5
C4 C5 C1 118.8(3)
C4 C5 H5 120.6
C1 C5 H5 120.6
C11 C6 C7 121.7(3)
C11 C6 S1 118.4(3)
C7 C6 S1 119.7(3)
C6 C7 C8 118.9(3)
C6 C7 H7 120.5
C8 C7 H7 120.5
C9 C8 C7 118.2(3)
C9 C8 H8 120.9
C7 C8 H8 120.9
C8 C9 C10 123.9(3)
C8 C9 N3 118.4(3)
C10 C9 N3 117.7(3)
C11 C10 C9 117.4(3)
C11 C10 H10 121.3
C9 C10 H10 121.3
C10 C11 C6 119.8(3)
C10 C11 H11 120.1
C6 C11 H11 120.1
C13 C12 Cl1 110.7(2)
C13 C12 Cl3 112.9(3)
Cl1 C12 Cl3 109.12(19)
C13 C12 Cl2 105.4(2)
Cl1 C12 Cl2 109.6(2)
Cl3 C12 Cl2 108.90(19)
O6 C13 O5 127.6(3)
O6 C13 C12 115.6(3)
O5 C13 C12 116.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.435(2)
S1 O1 1.436(3)
S1 N2 1.631(3)
S1 C6 1.766(4)
O3 N3 1.231(4)
O4 N3 1.227(4)
N1 C4 1.335(5)
N1 C3 1.341(5)
N1 H1 0.897(10)
N2 C1 1.390(4)
N2 H2 0.897(10)
N3 C9 1.472(5)
C1 C2 1.397(5)
C1 C5 1.405(5)
C2 C3 1.362(5)
C2 H2A 0.9300
C3 H3 0.9300
C4 C5 1.368(5)
C4 H4 0.9300
C5 H5 0.9300
C6 C11 1.388(5)
C6 C7 1.388(5)
C7 C8 1.394(5)
C7 H7 0.9300
C8 C9 1.372(5)
C8 H8 0.9300
C9 C10 1.387(5)
C10 C11 1.386(5)
C10 H10 0.9300
C11 H11 0.9300
Cl1 C12 1.765(4)
Cl2 C12 1.777(4)
Cl3 C12 1.770(4)
O5 C13 1.245(4)
O6 C13 1.231(4)
C12 C13 1.570(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O5 4_565 0.897(10) 1.755(13) 2.639(4) 168(4)
N2 H2 O6 1_565 0.897(10) 1.825(15) 2.707(4) 167(4)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 S1 N2 C1 -62.4(3)
O1 S1 N2 C1 167.2(3)
C6 S1 N2 C1 52.4(3)
S1 N2 C1 C2 -148.4(3)
S1 N2 C1 C5 32.5(5)
N2 C1 C2 C3 -178.7(3)
C5 C1 C2 C3 0.4(5)
C4 N1 C3 C2 0.3(6)
C1 C2 C3 N1 -0.3(6)
C3 N1 C4 C5 -0.4(6)
N1 C4 C5 C1 0.6(6)
N2 C1 C5 C4 178.5(3)
C2 C1 C5 C4 -0.6(5)
O2 S1 C6 C11 -174.3(3)
O1 S1 C6 C11 -41.5(3)
N2 S1 C6 C11 69.5(3)
O2 S1 C6 C7 9.9(3)
O1 S1 C6 C7 142.6(3)
N2 S1 C6 C7 -106.4(3)
C11 C6 C7 C8 -0.6(5)
S1 C6 C7 C8 175.1(3)
C6 C7 C8 C9 0.4(5)
C7 C8 C9 C10 0.8(6)
C7 C8 C9 N3 -177.4(3)
O4 N3 C9 C8 -11.3(5)
O3 N3 C9 C8 169.0(3)
O4 N3 C9 C10 170.3(3)
O3 N3 C9 C10 -9.4(5)
C8 C9 C10 C11 -1.8(6)
N3 C9 C10 C11 176.4(3)
C9 C10 C11 C6 1.6(5)
C7 C6 C11 C10 -0.4(5)
S1 C6 C11 C10 -176.2(3)
Cl1 C12 C13 O6 37.9(4)
Cl3 C12 C13 O6 160.6(3)
Cl2 C12 C13 O6 -80.6(3)
Cl1 C12 C13 O5 -144.5(3)
Cl3 C12 C13 O5 -21.8(4)
Cl2 C12 C13 O5 97.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119247
