#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/69/2006902.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_2006902
loop_
_publ_author_name
'Garcia, J. Gabriel'
'Haydar, Simon H.'
'Krapcho, A. Paul'
'Liu, Yen-Hsiang'
'Fronczek, Frank R.'
_publ_section_title
;
 2-(5-Chloro-2-nitrophenylthio)nicotinoyl Chloride
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              146
_journal_page_last               148
_journal_paper_doi               10.1107/S0108270197012870
_journal_volume                  54
_journal_year                    1998
_chemical_formula_sum            'C12 H6 Cl2 N2 O3 S'
_chemical_formula_weight         329.16
_chemical_name_systematic
;
2-(5-Chloro-2-nitrophenyl)thionicotinoyl Chloride
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90
_cell_angle_beta                 95.361(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8721(7)
_cell_length_b                   15.406(2)
_cell_length_c                   7.1392(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      29
_cell_measurement_theta_min      12
_cell_volume                     1300.1(2)
_computing_cell_refinement       CAD4_Software
_computing_data_collection       CAD4_Software_(Enraf-Nonius,_1977)
_computing_data_reduction        PROCESS_MolEN_(Fair,_1990)
_computing_molecular_graphics    ORTEPII_(Johnson,_1976)
_computing_publication_material  CIF_IN_MolEN
_computing_structure_refinement  LSFM_MolEN_(Fair,_1990)
_computing_structure_solution    Direct_methods_MULTAN80_(Main_et_al.,_1980)
_diffrn_measurement_device       Enraf_Nonius_CAD4
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.03
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2995
_diffrn_reflns_theta_max         74.92
_diffrn_standards_decay_%        -1.6
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    6.2
_exptl_absorpt_correction_T_max  0.22
_exptl_absorpt_correction_T_min  0.11
_exptl_absorpt_correction_type   \y_scans_(North,_Phillips_&_Mathews,_1968)
_exptl_crystal_colour            pale_yellow
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_description       irregular_fragment
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.47
_refine_ls_abs_structure_details
;
?
;
_refine_ls_extinction_coef       5.6E-6(3)
_refine_ls_extinction_method     isotropic_(Zachariasen,_1963)
_refine_ls_goodness_of_fit_obs   1.62
_refine_ls_hydrogen_treatment    H_atoms_refined_isotropically
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2566
_refine_ls_R_factor_obs          .047
_refine_ls_shift/esd_max         0.004
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 4Fo²/[σ²(Fo²) + 0.002Fo⁴]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         .061
_reflns_number_observed          2566
_reflns_number_total             2675
_reflns_observed_criterion       >1.0\s(I)
_cod_data_source_file            bk1348.cif
_cod_data_source_block           Gabriel81
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '4Fo^2^/[\s^2^(Fo^2^) +
0.002Fo^4^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.002Fo^4^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1300.1(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C12 H6 Cl2 N2 O3 S1'
_cod_database_code               2006902
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_thermal_displace_type
_atom_site_calc_flag
Cl1 -.06379(6) .17053(5) -.33410(10) Uani ?
Cl2 .72037(6) .15743(6) .29960(10) Uani ?
S .32536(4) .17150(3) .09857(8) Uani ?
O1 .5436(2) .22210(10) .1240(3) Uani ?
O2 .1399(2) .02700(10) .4984(3) Uani ?
O3 .2456(2) .13920(10) .4797(2) Uani ?
N1 .3359(2) .00400(10) .1927(3) Uani ?
N2 .1728(2) .08880(10) .4129(2) Uani ?
C1 .3967(2) .07580(10) .1773(3) Uani ?
C2 .5157(2) .07660(10) .2181(3) Uani ?
C3 .5688(2) -.00100(10) .2728(3) Uani ?
C4 .5059(2) -.07500(10) .2865(3) Uani ?
C5 .3905(2) -.06880(10) .2482(3) Uani ?
C6 .5783(2) .1580(2) .1986(3) Uani ?
C7 .1818(2) .13970(10) .0810(3) Uani ?
C8 .1199(2) .10530(10) .2230(3) Uani ?
C9 .0061(2) .0865(2) .1904(3) Uani ?
C10 -.0518(2) .1056(2) .0183(4) Uani ?
C11 .0071(2) .14260(10) -.1194(3) Uani ?
C12 .1224(2) .15770(10) -.0907(3) Uani ?
H3 .642(2) .002(2) .301(3) Uiso ?
H4 .539(2) -.133(2) .318(4) Uiso ?
H5 .341(2) -.117(2) .273(3) Uiso ?
H9 -.029(2) .067(2) .281(3) Uiso ?
H10 -.132(2) .091(2) -.002(3) Uiso ?
H12 .161(2) .181(2) -.195(3) Uiso ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 S C7 102.85(9) yes
C1 N1 C5 118.0(2) no
O2 N2 O3 123.3(2) ?
O2 N2 C8 118.1(2) ?
O3 N2 C8 118.5(2) ?
S C1 N1 118.1(2) ?
S C1 C2 119.9(2) ?
N1 C1 C2 121.9(2) ?
C1 C2 C3 118.0(2) ?
C1 C2 C6 119.4(2) ?
C3 C2 C6 122.6(2) ?
C2 C3 C4 119.9(2) ?
C2 C3 H3 115.0(10) ?
C4 C3 H3 124.0(10) ?
C3 C4 C5 117.8(2) ?
C3 C4 H4 123.0(10) ?
C5 C4 H4 118.0(10) ?
N1 C5 C4 124.3(2) ?
N1 C5 H5 114.0(10) ?
C4 C5 H5 121.0(10) ?
Cl2 C6 O1 117.9(2) yes
Cl2 C6 C2 115.4(2) yes
O1 C6 C2 126.7(2) yes
S C7 C8 128.1(2) ?
S C7 C12 114.6(2) ?
C8 C7 C12 117.1(2) ?
N2 C8 C7 121.6(2) ?
N2 C8 C9 116.6(2) ?
C7 C8 C9 121.7(2) ?
C8 C9 C10 120.1(2) ?
C8 C9 H9 119.0(10) ?
C10 C9 H9 120.0(10) ?
C9 C10 C11 118.6(2) ?
C9 C10 H10 118.0(10) ?
C11 C10 H10 122.0(10) ?
Cl1 C11 C10 119.7(2) ?
Cl1 C11 C12 118.8(2) ?
C10 C11 C12 121.5(2) ?
C7 C12 C11 120.8(2) ?
C7 C12 H12 120.0(10) ?
C11 C12 H12 118.0(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C11 1.733(2) yes
Cl2 C6 1.771(2) yes
S C1 1.766(2) yes
S C7 1.767(2) yes
O1 C6 1.178(3) no
O2 N2 1.215(3) no
O3 N2 1.224(3) ?
N1 C1 1.331(3) ?
N1 C5 1.338(3) ?
N2 C8 1.462(3) ?
C1 C2 1.415(3) ?
C2 C3 1.391(3) ?
C2 C6 1.471(3) ?
C3 C4 1.372(3) ?
C3 H3 .88(2) ?
C4 C5 1.375(3) ?
C4 H4 .99(3) ?
C5 H5 .97(3) ?
C7 C8 1.409(3) ?
C7 C12 1.384(3) ?
C8 C9 1.381(3) ?
C9 C10 1.382(3) ?
C9 H9 .85(2) ?
C10 C11 1.381(4) ?
C10 H10 .97(3) ?
C11 C12 1.384(3) ?
C12 H12 .98(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 85765764
