#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2221205.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_2221205
loop_
_publ_author_name
'Ng, Seik Weng'
_publ_section_title
;
 2-Chloroquinoxaline
;
_journal_coeditor_code           TK2366
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o455
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C8 H5 Cl N2'
_chemical_formula_moiety         'C8 H5 Cl N2'
_chemical_formula_sum            'C8 H5 Cl N2'
_chemical_formula_weight         164.59
_chemical_name_systematic
;
2-Chloroquinoxaline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.028(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1299(2)
_cell_length_b                   3.80820(10)
_cell_length_c                   21.0777(6)
_cell_measurement_reflns_used    1328
_cell_measurement_temperature    118(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      2.4
_cell_volume                     731.82(3)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6145
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.444
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+0.1632P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0990
_reflns_number_gt                1173
_reflns_number_total             1659
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    tk2366.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_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.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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_database_code               2221205
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Cl Cl1 0.60849(6) 0.47749(15) 0.58158(3) 0.03308(19) Uani d . 1
N N1 0.88157(18) 0.6668(4) 0.57567(8) 0.0202(4) Uani d . 1
N N2 0.8977(2) 0.9189(4) 0.70202(8) 0.0248(4) Uani d . 1
C C1 0.7733(2) 0.6552(5) 0.61274(10) 0.0219(5) Uani d . 1
C C2 0.7783(2) 0.7779(6) 0.67617(10) 0.0261(5) Uani d . 1
H H2 0.6938 0.7575 0.7003 0.031 Uiso calc R 1
C C3 1.0163(2) 0.9407(5) 0.66453(9) 0.0194(4) Uani d . 1
C C4 1.1478(2) 1.0934(5) 0.68919(10) 0.0231(5) Uani d . 1
H H4 1.1540 1.1816 0.7314 0.028 Uiso calc R 1
C C5 1.2662(2) 1.1150(5) 0.65264(10) 0.0250(5) Uani d . 1
H H5 1.3549 1.2165 0.6696 0.030 Uiso calc R 1
C C6 1.2576(2) 0.9872(5) 0.58970(10) 0.0254(5) Uani d . 1
H H6 1.3408 1.0049 0.5646 0.030 Uiso calc R 1
C C7 1.1318(2) 0.8385(5) 0.56422(10) 0.0214(4) Uani d . 1
H H7 1.1275 0.7528 0.5218 0.026 Uiso calc R 1
C C8 1.0086(2) 0.8132(5) 0.60139(9) 0.0179(4) Uani d . 1
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 0.0215(3) 0.0305(3) 0.0466(4) -0.0056(2) -0.0042(2) 0.0009(3)
N1 0.0187(9) 0.0178(8) 0.0239(9) 0.0000(7) -0.0020(7) 0.0008(7)
N2 0.0286(10) 0.0243(9) 0.0219(9) 0.0009(8) 0.0049(8) 0.0013(7)
C1 0.0190(10) 0.0185(10) 0.0277(11) -0.0005(8) -0.0029(9) 0.0043(9)
C2 0.0252(12) 0.0257(11) 0.0278(12) 0.0006(9) 0.0067(9) 0.0018(10)
C3 0.0234(10) 0.0148(9) 0.0200(10) 0.0022(8) 0.0005(8) 0.0027(8)
C4 0.0316(12) 0.0177(10) 0.0194(11) -0.0007(8) -0.0047(9) -0.0008(8)
C5 0.0247(11) 0.0198(10) 0.0296(12) -0.0018(8) -0.0066(9) 0.0028(9)
C6 0.0222(11) 0.0232(11) 0.0310(12) -0.0007(9) 0.0032(9) 0.0045(10)
C7 0.0256(11) 0.0192(10) 0.0195(10) 0.0028(9) 0.0019(8) 0.0000(9)
C8 0.0188(10) 0.0144(9) 0.0201(10) 0.0014(8) -0.0031(8) 0.0028(8)
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'
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
C1 N1 C8 115.61(17)
C2 N2 C3 116.68(18)
N1 C1 C2 124.93(19)
N1 C1 Cl1 117.21(16)
C2 C1 Cl1 117.87(16)
N2 C2 C1 120.92(19)
N2 C2 H2 119.5
C1 C2 H2 119.5
N2 C3 C4 119.62(18)
N2 C3 C8 121.21(18)
C4 C3 C8 119.18(18)
C5 C4 C3 120.18(19)
C5 C4 H4 119.9
C3 C4 H4 119.9
C4 C5 C6 120.3(2)
C4 C5 H5 119.9
C6 C5 H5 119.9
C7 C6 C5 121.13(19)
C7 C6 H6 119.4
C5 C6 H6 119.4
C6 C7 C8 119.33(19)
C6 C7 H7 120.3
C8 C7 H7 120.3
N1 C8 C7 119.43(18)
N1 C8 C3 120.65(18)
C7 C8 C3 119.91(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.746(2)
N1 C1 1.293(3)
N1 C8 1.372(2)
N2 C2 1.308(3)
N2 C3 1.376(3)
C1 C2 1.415(3)
C2 H2 0.9500
C3 C4 1.409(3)
C3 C8 1.415(3)
C4 C5 1.363(3)
C4 H4 0.9500
C5 C6 1.411(3)
C5 H5 0.9500
C6 C7 1.365(3)
C6 H6 0.9500
C7 C8 1.408(3)
C7 H7 0.9500
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
C8 N1 C1 C2 -0.5(3)
C8 N1 C1 Cl1 178.97(14)
C3 N2 C2 C1 0.0(3)
N1 C1 C2 N2 0.6(3)
Cl1 C1 C2 N2 -178.91(16)
C2 N2 C3 C4 179.27(19)
C2 N2 C3 C8 -0.5(3)
N2 C3 C4 C5 179.69(18)
C8 C3 C4 C5 -0.5(3)
C3 C4 C5 C6 0.5(3)
C4 C5 C6 C7 -0.3(3)
C5 C6 C7 C8 0.2(3)
C1 N1 C8 C7 -179.61(18)
C1 N1 C8 C3 0.0(3)
C6 C7 C8 N1 179.40(18)
C6 C7 C8 C3 -0.2(3)
N2 C3 C8 N1 0.6(3)
C4 C3 C8 N1 -179.22(18)
N2 C3 C8 C7 -179.87(17)
C4 C3 C8 C7 0.3(3)