#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/27/2212701.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_2212701
loop_
_publ_author_name
'Cheng, Yu'
'An, Lin-Kun'
'Gu, Lian-Quan'
'Ng, Seik Weng'
_publ_section_title
;
 6,6,7,7-Tetrachloro-5,6,7,8-tetrahydroquinoline-5,8-dione
;
_journal_coeditor_code           SJ2223
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1365
_journal_page_last               o1366
_journal_paper_doi               10.1107/S1600536807007398
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C9 H3 Cl4 N O2'
_chemical_formula_moiety         'C9 H3 Cl4 N O2'
_chemical_formula_sum            'C9 H3 Cl4 N O2'
_chemical_formula_weight         298.92
_chemical_name_systematic
;
6,6,7,7-Tetrachloro-5,6,7,8-tetrahydroquinoline-5,8-dione
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6115(4)
_cell_length_b                   10.3015(6)
_cell_length_c                   14.1723(8)
_cell_measurement_reflns_used    4235
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.4
_cell_volume                     1111.25(11)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Bruker SMART area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6576
_diffrn_reflns_theta_full        27.1
_diffrn_reflns_theta_max         27.05
_diffrn_reflns_theta_min         2.44
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.045
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Irregular block'
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.36
_refine_ls_abs_structure_details 'Flack (1983), 1012 Friedel pairs'
_refine_ls_abs_structure_Flack   0.10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.052
_refine_ls_R_factor_gt           0.047
_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)+(0.0832P)²+0.5204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.134
_refine_ls_wR_factor_ref         0.139
_reflns_number_gt                2195
_reflns_number_total             2436
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2223.cif
_cod_data_source_block           I
_cod_original_cell_volume        1111.30(10)
_cod_database_code               2212701
_cod_database_fobs_code          2212701
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
Cl Cl1 0.6837(2) 1.07380(10) 0.29450(10) 0.0731(4) Uani d . 1
Cl Cl2 0.5294(2) 0.8383(2) 0.37392(8) 0.0771(4) Uani d . 1
Cl Cl3 0.8557(2) 0.96580(10) 0.48699(7) 0.0650(3) Uani d . 1
Cl Cl4 0.9238(2) 0.72090(10) 0.38760(7) 0.0788(4) Uani d . 1
O O1 0.6123(3) 0.7922(4) 0.1804(2) 0.0632(9) Uani d . 1
O O2 1.1445(4) 1.0148(4) 0.3620(2) 0.0737(10) Uani d . 1
N N1 0.9195(4) 0.8203(3) 0.0822(2) 0.0445(7) Uani d . 1
C C1 1.0745(6) 0.8354(4) 0.0395(3) 0.0494(9) Uani d . 1
H H1 1.0838 0.8092 -0.0232 0.059 Uiso calc R 1
C C2 1.2200(5) 0.8864(4) 0.0814(3) 0.0518(9) Uani d . 1
H H2 1.3244 0.8948 0.0479 0.062 Uiso calc R 1
C C3 1.2102(5) 0.9254(4) 0.1741(3) 0.0505(9) Uani d . 1
H H3 1.3069 0.9619 0.2042 0.061 Uiso calc R 1
C C4 1.0522(5) 0.9088(3) 0.2218(2) 0.0374(7) Uani d . 1
C C5 1.0388(5) 0.9500(4) 0.3227(3) 0.0474(8) Uani d . 1
C C6 0.8792(6) 0.8921(4) 0.3759(3) 0.0516(9) Uani d . 1
C C7 0.7150(5) 0.9025(4) 0.3170(3) 0.0489(9) Uani d . 1
C C8 0.7356(5) 0.8397(4) 0.2182(2) 0.0420(8) Uani d . 1
C C9 0.9104(4) 0.8563(3) 0.1731(2) 0.0337(6) 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 0.0840(8) 0.0591(6) 0.0762(7) 0.0339(6) 0.0152(6) 0.0031(5)
Cl2 0.0641(7) 0.1226(11) 0.0446(6) -0.0355(7) 0.0198(5) -0.0101(6)
Cl3 0.0719(7) 0.0856(7) 0.0376(5) -0.0054(6) 0.0051(5) -0.0271(5)
Cl4 0.1440(10) 0.0507(5) 0.0421(5) 0.0215(7) -0.0030(7) 0.0096(4)
O1 0.043(2) 0.103(2) 0.043(2) -0.019(2) -0.0010(10) -0.017(2)
O2 0.055(2) 0.098(2) 0.069(2) -0.020(2) -0.002(2) -0.047(2)
N1 0.049(2) 0.059(2) 0.0260(10) 0.0020(10) 0.0000(10) 0.0000(10)
C1 0.058(2) 0.061(2) 0.029(2) 0.010(2) 0.009(2) 0.002(2)
C2 0.044(2) 0.064(2) 0.048(2) 0.000(2) 0.013(2) 0.000(2)
C3 0.034(2) 0.061(2) 0.057(2) -0.005(2) 0.006(2) -0.006(2)
C4 0.037(2) 0.037(2) 0.038(2) 0.0060(10) 0.0030(10) -0.0030(10)
C5 0.040(2) 0.057(2) 0.045(2) 0.000(2) -0.003(2) -0.015(2)
C6 0.062(2) 0.058(2) 0.035(2) -0.003(2) 0.001(2) -0.011(2)
C7 0.043(2) 0.066(2) 0.038(2) -0.004(2) 0.010(2) -0.005(2)
C8 0.045(2) 0.052(2) 0.029(2) -0.008(2) 0.0000(10) -0.003(2)
C9 0.038(2) 0.0340(10) 0.0290(10) 0.0020(10) -0.0030(10) 0.0010(10)
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'
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 C9 116.6(3)
N1 C1 C2 124.4(3)
C1 C2 C3 119.0(4)
C2 C3 C4 118.4(4)
C3 C4 C9 118.5(3)
C3 C4 C5 119.3(3)
C9 C4 C5 122.2(3)
O2 C5 C4 124.3(4)
O2 C5 C6 121.4(4)
C4 C5 C6 114.2(3)
C7 C6 C5 110.7(3)
C7 C6 Cl3 112.4(3)
C5 C6 Cl3 110.5(3)
C7 C6 Cl4 106.1(3)
C5 C6 Cl4 105.9(3)
Cl3 C6 Cl4 111.0(2)
C6 C7 C8 112.7(3)
C6 C7 Cl2 112.7(3)
C8 C7 Cl2 109.8(3)
C6 C7 Cl1 106.1(3)
C8 C7 Cl1 105.1(3)
Cl2 C7 Cl1 110.0(2)
O1 C8 C9 124.1(3)
O1 C8 C7 120.1(3)
C9 C8 C7 115.5(3)
N1 C9 C4 123.0(3)
N1 C9 C8 115.3(3)
C4 C9 C8 121.7(3)
N1 C1 H1 117.8
C2 C1 H1 117.8
C1 C2 H2 120.5
C3 C2 H2 120.5
C2 C3 H3 120.8
C4 C3 H3 120.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C7 1.809(4)
Cl2 C7 1.756(4)
Cl3 C6 1.757(4)
Cl4 C6 1.804(4)
O1 C8 1.186(4)
O2 C5 1.185(5)
N1 C1 1.335(5)
N1 C9 1.343(4)
C1 C2 1.363(6)
C2 C3 1.376(6)
C3 C4 1.390(5)
C4 C9 1.391(5)
C4 C5 1.494(5)
C5 C6 1.550(6)
C6 C7 1.506(6)
C7 C8 1.551(5)
C8 C9 1.487(5)
C1 H1 0.93
C2 H2 0.93
C3 H3 0.93
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
C9 N1 C1 C2 -1.3(6)
N1 C1 C2 C3 0.3(7)
C1 C2 C3 C4 1.1(6)
C2 C3 C4 C9 -1.4(6)
C2 C3 C4 C5 179.8(4)
C3 C4 C5 O2 12.4(6)
C9 C4 C5 O2 -166.3(4)
C3 C4 C5 C6 -163.3(3)
C9 C4 C5 C6 18.0(5)
O2 C5 C6 C7 138.6(4)
C4 C5 C6 C7 -45.5(4)
O2 C5 C6 Cl3 13.4(5)
C4 C5 C6 Cl3 -170.7(3)
O2 C5 C6 Cl4 -106.9(4)
C4 C5 C6 Cl4 69.0(4)
C5 C6 C7 C8 55.0(4)
Cl3 C6 C7 C8 179.1(3)
Cl4 C6 C7 C8 -59.4(4)
C5 C6 C7 Cl2 180.0(3)
Cl3 C6 C7 Cl2 -55.9(4)
Cl4 C6 C7 Cl2 65.6(3)
C5 C6 C7 Cl1 -59.5(3)
Cl3 C6 C7 Cl1 64.5(3)
Cl4 C6 C7 Cl1 -173.9(2)
C6 C7 C8 O1 148.9(4)
Cl2 C7 C8 O1 22.4(5)
Cl1 C7 C8 O1 -96.0(4)
C6 C7 C8 C9 -37.2(5)
Cl2 C7 C8 C9 -163.8(3)
Cl1 C7 C8 C9 77.8(3)
C1 N1 C9 C4 0.9(5)
C1 N1 C9 C8 179.4(3)
C3 C4 C9 N1 0.4(5)
C5 C4 C9 N1 179.2(3)
C3 C4 C9 C8 -177.9(3)
C5 C4 C9 C8 0.8(5)
O1 C8 C9 N1 3.7(6)
C7 C8 C9 N1 -169.9(3)
O1 C8 C9 C4 -177.9(4)
C7 C8 C9 C4 8.6(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125134
