#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:53:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180522 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/91/7219191.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7219191
loop_
_publ_author_name
'Hu, Yanjing'
'Li, Zhiqiang'
'Zhao, Yiran'
'Yang, Yu'
'Liu, Faqian'
'Wang, Lei'
_publ_section_title
;
 Using Halogen•••Halogen Interactions or
 C/N--H•••Cl Hydrogen Bonding to Direct Crystal
 Packing in Tetrachlorophthalic Acid with N--heterocyclic Compounds
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA15392H
_journal_year                    2014
_chemical_formula_moiety         'C32 H22 Cl8 N4 O8'
_chemical_formula_sum            'C32 H22 Cl8 N4 O8'
_chemical_formula_weight         874.14
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-11-28 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;
_cell_angle_alpha                88.1770(10)
_cell_angle_beta                 73.7680(10)
_cell_angle_gamma                87.1080(10)
_cell_formula_units_Z            1
_cell_length_a                   8.5055(6)
_cell_length_b                   9.8663(7)
_cell_length_c                   11.0901(7)
_cell_measurement_temperature    293(2)
_cell_volume                     892.27(11)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0567
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4639
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  0.0001
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             442
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.512
_refine_diff_density_min         -0.930
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3107
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0653
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0906P)²+2.0005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1736
_refine_ls_wR_factor_ref         0.1787
_reflns_number_gt                2808
_reflns_number_total             3107
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra15392h2.cif
_cod_data_source_block           compound3
_cod_database_code               7219191
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl4 Cl 0.19975(11) -0.36321(11) 0.13914(10) 0.0450(3) Uani 1 1 d . . .
Cl1 Cl 0.85105(12) -0.56451(11) 0.24716(11) 0.0486(3) Uani 1 1 d . . .
Cl3 Cl 0.52821(13) -0.24508(11) -0.01709(10) 0.0496(3) Uani 1 1 d . . .
Cl2 Cl 0.85358(12) -0.33833(12) 0.04252(11) 0.0491(3) Uani 1 1 d . . .
O4 O 0.1357(4) -0.4662(3) 0.4274(3) 0.0458(7) Uani 1 1 d . . .
O1 O 0.5027(5) -0.6254(3) 0.4970(3) 0.0548(9) Uani 1 1 d . . .
O3 O 0.1774(4) -0.6736(3) 0.3528(3) 0.0545(8) Uani 1 1 d . . .
O2 O 0.5529(5) -0.7884(3) 0.3577(3) 0.0583(9) Uani 1 1 d . . .
C9 C 0.5252(4) -0.5616(3) 0.2855(3) 0.0275(7) Uani 1 1 d . . .
C10 C 0.3773(4) -0.5109(3) 0.2674(3) 0.0270(7) Uani 1 1 d . . .
C11 C 0.6732(4) -0.4078(4) 0.1244(3) 0.0311(8) Uani 1 1 d . . .
C12 C 0.2172(4) -0.5579(4) 0.3537(3) 0.0306(8) Uani 1 1 d . . .
C13 C 0.0026(6) 0.0423(4) 0.1181(4) 0.0424(9) Uani 1 1 d . . .
C14 C 0.6711(4) -0.5089(4) 0.2155(3) 0.0312(8) Uani 1 1 d . . .
C15 C 0.3800(4) -0.4148(4) 0.1720(3) 0.0296(7) Uani 1 1 d . . .
C16 C 0.5264(4) -0.3628(4) 0.1007(3) 0.0310(8) Uani 1 1 d . . .
C17 C 0.5271(5) -0.6700(4) 0.3865(4) 0.0348(8) Uani 1 1 d . . .
C18 C 0.1394(6) -0.0243(4) 0.0393(5) 0.0484(10) Uani 1 1 d . . .
H18 H 0.2338 -0.0401 0.0652 0.080 Uiso 1 1 calc . . .
N1 N 0.0770(7) -0.0086(4) 0.3165(4) 0.0624(12) Uani 1 1 d . . .
C20 C -0.1352(6) 0.0672(4) 0.0775(4) 0.0480(10) Uani 1 1 d . . .
H20 H -0.2263 0.1131 0.1290 0.080 Uiso 1 1 calc . . .
C21 C 0.0070(7) 0.0927(4) 0.2444(5) 0.0564(12) Uani 1 1 d . . .
H21A H 0.0711 0.1731 0.2316 0.068 Uiso 1 1 calc R . .
H21B H -0.1037 0.1185 0.2927 0.068 Uiso 1 1 calc R . .
N2 N 0.1277(16) -0.1859(6) 0.4143(6) 0.168(6) Uani 1.00(3) 1 d U A 1
H2 H 0.1150 -0.2631 0.4532 0.080 Uiso 1 1 calc . B 1
C23 C -0.1480(18) -0.1676(12) 0.3635(7) 0.186(7) Uani 1 1 d . A 1
H23A H -0.2282 -0.0944 0.3891 0.278 Uiso 1 1 calc R A 1
H23B H -0.1775 -0.2436 0.4202 0.278 Uiso 1 1 calc R A 1
H23C H -0.1440 -0.1938 0.2800 0.278 Uiso 1 1 calc R A 1
C24 C 0.0147(14) -0.1229(6) 0.3652(5) 0.116(4) Uani 1 1 d . A 1
C25 C 0.2315(10) -0.0032(7) 0.3353(6) 0.086(2) Uani 1 1 d . A 1
H25 H 0.3015 0.0680 0.3090 0.103 Uiso 1 1 calc R A 1
C26 C 0.2644(18) -0.1127(8) 0.3952(9) 0.139(5) Uani 1 1 d . A 1
H26 H 0.3590 -0.1353 0.4191 0.167 Uiso 1 1 calc R A 1
H4 H 0.055(11) -0.487(10) 0.470(9) 0.04(3) Uiso 0.50 1 d P . .
H1 H 0.5000 -0.5000 0.5000 0.08(2) Uiso 1 2 d S . .
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C14 C9 C10 119.8(3) . .
C14 C9 C17 119.6(3) . .
C10 C9 C17 120.5(3) . .
C9 C10 C15 119.1(3) . .
C9 C10 C12 119.6(3) . .
C15 C10 C12 121.2(3) . .
C14 C11 C16 119.3(3) . .
C14 C11 Cl2 120.6(3) . .
C16 C11 Cl2 120.0(3) . .
O3 C12 O4 125.1(3) . .
O3 C12 C10 121.1(3) . .
O4 C12 C10 113.7(3) . .
C20 C13 C18 119.3(4) . .
C20 C13 C21 120.0(4) . .
C18 C13 C21 120.7(4) . .
C9 C14 C11 121.0(3) . .
C9 C14 Cl1 119.0(3) . .
C11 C14 Cl1 120.0(3) . .
C16 C15 C10 121.0(3) . .
C16 C15 Cl4 119.4(3) . .
C10 C15 Cl4 119.5(3) . .
C15 C16 C11 119.5(3) . .
C15 C16 Cl3 120.6(3) . .
C11 C16 Cl3 119.9(3) . .
O2 C17 O1 125.2(4) . .
O2 C17 C9 119.7(4) . .
O1 C17 C9 115.1(3) . .
C20 C18 C13 120.2(4) 2 .
C24 N1 C25 108.0(6) . .
C24 N1 C21 127.4(6) . .
C25 N1 C21 124.5(5) . .
C13 C20 C18 120.5(4) . 2
N1 C21 C13 113.1(4) . .
C24 N2 C26 112.0(6) . .
N1 C24 N2 105.9(8) . .
N1 C24 C23 124.7(9) . .
N2 C24 C23 129.5(7) . .
C26 C25 N1 110.2(9) . .
C25 C26 N2 103.9(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl4 C15 1.722(3) .
Cl1 C14 1.724(4) .
Cl3 C16 1.717(4) .
Cl2 C11 1.713(4) .
O4 C12 1.279(5) .
O1 C17 1.273(5) .
O3 C12 1.208(5) .
O2 C17 1.214(5) .
C9 C14 1.384(5) .
C9 C10 1.394(5) .
C9 C17 1.527(5) .
C10 C15 1.395(5) .
C10 C12 1.514(5) .
C11 C14 1.394(5) .
C11 C16 1.394(5) .
C13 C20 1.377(6) .
C13 C18 1.393(6) .
C13 C21 1.512(6) .
C15 C16 1.388(5) .
C18 C20 1.386(7) 2
N1 C24 1.306(7) .
N1 C25 1.391(9) .
N1 C21 1.466(6) .
C20 C18 1.386(7) 2
N2 C24 1.349(14) .
N2 C26 1.361(16) .
C23 C24 1.479(14) .
C25 C26 1.310(9) .
