#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:53:30 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180522 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/91/7219190.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_7219190
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         '(C8 H Cl4 O4),(C2 H5 N4)'
_chemical_formula_sum            'C10 H6 Cl4 N4 O4'
_chemical_formula_weight         387.99
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-21
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.20 svn.r3092 for OlexSys, GUI svn.r4949)
;
_audit_update_record
;
2014-11-28 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.4206(3)
_cell_length_b                   12.0251(3)
_cell_length_c                   24.0488(9)
_cell_measurement_temperature    293(2)
_cell_volume                     2724.34(15)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8878
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.75
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.892
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.892
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0306
_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)+(0.0246P)²+1.3405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0705
_reflns_number_gt                2448
_reflns_number_total             2950
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra15392h2.cif
_cod_data_source_block           compound2
_cod_database_code               7219190
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3A), N4(H4), C17(H17)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 'x, -y-1/2, z-1/2'
8 '-x-1/2, y-1/2, 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_calc_flag
_atom_site_refinement_flags_posn
Cl1 Cl 0.09841(6) 0.09932(4) 0.33185(2) 0.03394(14) Uani 1 d .
Cl2 Cl -0.16960(6) -0.12574(4) 0.17012(2) 0.03715(14) Uani 1 d .
Cl3 Cl -0.33902(5) -0.25775(4) 0.25874(2) 0.03202(13) Uani 1 d .
Cl4 Cl 0.05026(6) 0.05212(4) 0.20661(2) 0.03354(14) Uani 1 d .
O1 O 0.00045(15) -0.11661(11) 0.43952(6) 0.0335(3) Uani 1 d .
O2 O -0.10407(15) 0.04779(10) 0.43441(6) 0.0302(3) Uani 1 d .
C3 C -0.1405(2) -0.10227(15) 0.23951(8) 0.0240(4) Uani 1 d .
N3 N 0.27850(18) -0.43803(13) 0.46691(7) 0.0320(4) Uani 1 d .
H3A H 0.3564 -0.4669 0.4787 0.038 Uiso 1 calc R
C5 C -0.09244(19) -0.06315(14) 0.35236(8) 0.0217(4) Uani 1 d .
C6 C -0.0432(2) -0.02176(14) 0.25586(8) 0.0236(4) Uani 1 d .
C7 C -0.02094(19) -0.00155(14) 0.31191(8) 0.0231(4) Uani 1 d .
C8 C -0.06354(19) -0.04226(15) 0.41339(8) 0.0232(4) Uani 1 d .
O3 O -0.23681(16) -0.31893(10) 0.37757(6) 0.0339(3) Uani 1 d .
H3 H -0.2948 -0.3535 0.3962 0.051 Uiso 1 calc GR
C10 C -0.26514(19) -0.21190(15) 0.38028(8) 0.0237(4) Uani 1 d .
C11 C -0.21165(19) -0.16391(14) 0.27976(8) 0.0224(4) Uani 1 d .
O4 O -0.34143(15) -0.16828(12) 0.41380(6) 0.0380(4) Uani 1 d .
N2 N 0.1579(2) -0.49803(15) 0.45566(8) 0.0383(4) Uani 1 d .
C14 C -0.18665(19) -0.14633(14) 0.33613(8) 0.0217(4) Uani 1 d .
N4 N 0.1260(2) -0.31959(15) 0.43973(8) 0.0389(5) Uani 1 d .
H4 H 0.0843 -0.2588 0.4303 0.047 Uiso 1 calc R
C16 C 0.2608(2) -0.33049(16) 0.45747(9) 0.0320(5) Uani 1 d .
C17 C 0.0685(2) -0.42352(19) 0.43956(10) 0.0426(6) Uani 1 d .
H17 H -0.0245 -0.4389 0.4290 0.051 Uiso 1 calc R
N1 N 0.3566(2) -0.25153(16) 0.46328(10) 0.0514(6) Uani 1 d .
H1A H 0.4409 -0.2679 0.4743 0.062 Uiso 1 calc R
H1B H 0.3348 -0.1836 0.4561 0.062 Uiso 1 calc R
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
C6 C3 Cl2 119.69(15)
C6 C3 C11 119.46(18)
C11 C3 Cl2 120.85(15)
C16 N3 N2 112.05(17)
C7 C5 C8 120.05(16)
C14 C5 C7 119.55(18)
C14 C5 C8 120.36(16)
C3 C6 Cl4 120.12(15)
C7 C6 Cl4 120.06(14)
C7 C6 C3 119.82(17)
C5 C7 Cl1 119.66(15)
C6 C7 Cl1 119.56(14)
C6 C7 C5 120.77(17)
O1 C8 O2 124.24(18)
O1 C8 C5 117.13(16)
O2 C8 C5 118.63(16)
O3 C10 C14 112.05(16)
O4 C10 O3 125.58(18)
O4 C10 C14 122.36(16)
C3 C11 Cl3 118.69(15)
C3 C11 C14 121.01(17)
C14 C11 Cl3 120.20(14)
C17 N2 N3 103.56(17)
C5 C14 C10 119.23(17)
C11 C14 C5 119.32(17)
C11 C14 C10 121.38(16)
C16 N4 C17 106.68(17)
N3 C16 N4 105.56(19)
N1 C16 N3 126.9(2)
N1 C16 N4 127.56(19)
N2 C17 N4 112.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C7 1.7220(19)
Cl2 C3 1.714(2)
Cl3 C11 1.7230(18)
Cl4 C6 1.7228(19)
O1 C8 1.248(2)
O2 C8 1.254(2)
C3 C6 1.390(3)
C3 C11 1.391(3)
N3 N2 1.373(2)
N3 C16 1.324(2)
C5 C7 1.396(3)
C5 C8 1.514(3)
C5 C14 1.393(3)
C6 C7 1.386(3)
O3 C10 1.316(2)
C10 O4 1.201(2)
C10 C14 1.515(3)
C11 C14 1.392(3)
N2 C17 1.289(3)
N4 C16 1.346(3)
N4 C17 1.362(3)
C16 N1 1.317(3)
