#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2006902.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. G.'
'Haydar, S. H.'
'Krapcho, A. P.'
'Liu, Y.-H.'
'Fronczek, F. 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_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       \q/2\q
_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          0.047
_refine_ls_shift/esd_max         0.004
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      '4Fo^2^/[\s^2^(Fo^2^) + 0.002Fo^4^]'
_refine_ls_wR_factor_obs         0.061
_reflns_number_observed          2566
_reflns_number_total             2675
_reflns_observed_criterion       >1.0\s(I)
_[local]_cod_data_source_file    bk1348.cif
_[local]_cod_data_source_block   Gabriel81
_[local]_cod_chemical_formula_sum_orig 'C12 H6 Cl2 N2 O3 S1'
_cod_original_cell_volume        1300.1(3)
_cod_database_code               2006902
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0722(4) 0.0731(4) 0.0613(3) 0.0133(3) -0.0207(3) -0.0015(3)
Cl2 0.0438(3) 0.0790(5) 0.1158(6) -0.0105(3) -0.0072(4) 0.0064(4)
S 0.0381(2) 0.0315(2) 0.0610(3) 0.0010(2) 0.0066(2) 0.0104(2)
O1 0.0527(9) 0.0406(8) 0.1100(10) -0.0070(8) 0.0040(10) 0.0140(9)
O2 0.0730(10) 0.0630(10) 0.0670(10) -0.0072(9) 0.0105(9) 0.0256(8)
O3 0.0680(10) 0.0558(9) 0.0494(8) -0.0073(9) -0.0043(8) -0.0022(8)
N1 0.0452(8) 0.0308(7) 0.0518(9) -0.0008(7) 0.0087(7) 0.0022(7)
N2 0.0477(9) 0.0397(9) 0.0462(8) 0.0047(8) 0.0091(7) 0.0037(7)
C1 0.0415(9) 0.0313(8) 0.0379(8) 0.0023(8) 0.0075(7) 0.0017(7)
C2 0.0414(9) 0.0357(9) 0.0387(9) 0.0017(8) 0.0080(7) -0.0007(8)
C3 0.0440(10) 0.0450(10) 0.0450(10) 0.0099(9) 0.0053(8) 0.0015(9)
C4 0.0600(10) 0.0348(9) 0.0490(10) 0.0110(10) 0.0068(9) 0.0047(9)
C5 0.0550(10) 0.0299(9) 0.0530(10) 0.0004(9) 0.0116(9) 0.0029(8)
C6 0.0390(9) 0.0440(10) 0.0560(10) -0.0011(9) 0.0068(9) -0.0044(9)
C7 0.0397(9) 0.0294(8) 0.0460(10) 0.0035(8) 0.0066(8) 0.0008(8)
C8 0.0436(9) 0.0321(9) 0.0436(9) 0.0030(8) 0.0051(8) -0.0005(8)
C9 0.0427(9) 0.0440(10) 0.0580(10) -0.0028(9) 0.0138(9) -0.0010(10)
C10 0.0400(10) 0.0480(10) 0.0670(10) 0.0010(10) 0.0020(10) -0.0100(10)
C11 0.0510(10) 0.0380(10) 0.0490(10) 0.0070(9) -0.0058(9) -0.0071(9)
C12 0.0480(10) 0.0376(9) 0.0460(10) 0.0048(9) 0.0061(9) 0.0012(9)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_thermal_displace_type
Cl1 -0.06379(6) 0.17053(5) -0.33410(10) Uani
Cl2 0.72037(6) 0.15743(6) 0.29960(10) Uani
S 0.32536(4) 0.17150(3) 0.09857(8) Uani
O1 0.5436(2) 0.22210(10) 0.1240(3) Uani
O2 0.1399(2) 0.02700(10) 0.4984(3) Uani
O3 0.2456(2) 0.13920(10) 0.4797(2) Uani
N1 0.3359(2) 0.00400(10) 0.1927(3) Uani
N2 0.1728(2) 0.08880(10) 0.4129(2) Uani
C1 0.3967(2) 0.07580(10) 0.1773(3) Uani
C2 0.5157(2) 0.07660(10) 0.2181(3) Uani
C3 0.5688(2) -0.00100(10) 0.2728(3) Uani
C4 0.5059(2) -0.07500(10) 0.2865(3) Uani
C5 0.3905(2) -0.06880(10) 0.2482(3) Uani
C6 0.5783(2) 0.1580(2) 0.1986(3) Uani
C7 0.1818(2) 0.13970(10) 0.0810(3) Uani
C8 0.1199(2) 0.10530(10) 0.2230(3) Uani
C9 0.0061(2) 0.0865(2) 0.1904(3) Uani
C10 -0.0518(2) 0.1056(2) 0.0183(4) Uani
C11 0.0071(2) 0.14260(10) -0.1194(3) Uani
C12 0.1224(2) 0.15770(10) -0.0907(3) Uani
H3 0.642(2) 0.002(2) 0.301(3) Uiso
H4 0.539(2) -0.133(2) 0.318(4) Uiso
H5 0.341(2) -0.117(2) 0.273(3) Uiso
H9 -0.029(2) 0.067(2) 0.281(3) Uiso
H10 -0.132(2) 0.091(2) -0.002(3) Uiso
H12 0.161(2) 0.181(2) -0.195(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 0.88(2) ?
C4 C5 1.375(3) ?
C4 H4 0.99(3) ?
C5 H5 0.97(3) ?
C7 C8 1.409(3) ?
C7 C12 1.384(3) ?
C8 C9 1.381(3) ?
C9 C10 1.382(3) ?
C9 H9 0.85(2) ?
C10 C11 1.381(4) ?
C10 H10 0.97(3) ?
C11 C12 1.384(3) ?
C12 H12 0.98(3) ?