#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/73/2017330.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_2017330
loop_
_publ_author_name
'He, Ming-Yang'
'Zhang, Zhi-Hui'
'Lu, Lu-De'
'Yang, Xu-Jie'
'Wang, Xin'
_publ_section_title
;
 Hydrogen-bond-directed supramolecular arrays in 4,4'-bipyridinium
 tetrachloroterephthalate dihydrate and bis(1,10-phenanthrolinium)
 tetrachloroterephthalate tetrachloroterephthalic acid trihydrate
;
_journal_coeditor_code           FG3128
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o525
_journal_page_last               o528
_journal_paper_doi               10.1107/S0108270109037500
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac
'2C12 H9 N2 +, C8 Cl4 O4 2-, C8 H2 Cl4 O4, 3H2 O'
_chemical_formula_moiety
'2(C12 H9 N2 +), C8 Cl4 O4 2-, C8 H2 Cl4 O4, 3(H2 O)'
_chemical_formula_sum            'C40 H26 Cl8 N4 O11'
_chemical_formula_weight         1022.25
_chemical_name_systematic
;
bis(1,10-phenanthrolinium) tetrachloroterephthalate tetrachloroterephthalic
acid trihydrate
;
_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
_cell_angle_alpha                102.127(2)
_cell_angle_beta                 109.4540(10)
_cell_angle_gamma                106.072(2)
_cell_formula_units_Z            1
_cell_length_a                   8.2931(11)
_cell_length_b                   12.0916(16)
_cell_length_c                   12.3108(16)
_cell_measurement_reflns_used    4670
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.448
_cell_measurement_theta_min      2.144
_cell_volume                     1054.4(2)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7609
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  0.9153
_exptl_absorpt_correction_T_min  0.8498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             518
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.383
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3677
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0444
_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)+(0.0850P)²+0.8354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1467
_reflns_number_gt                3201
_reflns_number_total             3677
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            fg3128.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_original_sg_symbol_H-M      P-1
_cod_database_code               2017330
_cod_database_fobs_code          2017330
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C13 0.8004(4) 0.6428(2) 0.3931(3) 0.0349(6) Uani d . 1 . .
C C14 0.9036(4) 0.5691(2) 0.4489(2) 0.0327(6) Uani d . 1 . .
C C15 0.9437(4) 0.4846(3) 0.3768(2) 0.0354(6) Uani d . 1 . .
C C16 1.0369(4) 0.4155(2) 0.4264(2) 0.0345(6) Uani d . 1 . .
C C17 0.3805(4) 0.6728(2) 0.1275(2) 0.0328(6) Uani d . 1 . .
C C18 0.4441(3) 0.5832(2) 0.0631(2) 0.0310(6) Uani d . 1 . .
C C19 0.5945(4) 0.6239(2) 0.0353(2) 0.0337(6) Uani d . 1 . .
C C20 0.6511(3) 0.5427(2) -0.0266(2) 0.0316(6) Uani d . 1 . .
Cl Cl1 0.87168(13) 0.46445(9) 0.22274(7) 0.0581(3) Uani d . 1 . .
Cl Cl2 1.08249(13) 0.30984(8) 0.33555(7) 0.0551(3) Uani d . 1 . .
Cl Cl3 0.71191(12) 0.78008(7) 0.07764(8) 0.0540(3) Uani d . 1 . .
Cl Cl4 0.84232(11) 0.59513(7) -0.05612(9) 0.0551(3) Uani d . 1 . .
O O1 0.6217(3) 0.58790(18) 0.3543(2) 0.0429(5) Uani d . 1 . .
H H1' 0.5692 0.6279 0.3211 0.064 Uiso calc R 1 . .
O O2 0.8792(3) 0.7397(2) 0.3880(3) 0.0637(7) Uani d . 1 . .
O O3 0.4225(3) 0.68953(18) 0.24061(17) 0.0389(5) Uani d . 1 . .
O O4 0.2923(3) 0.7218(2) 0.06687(19) 0.0474(5) Uani d . 1 . .
C C1 0.4661(4) 0.6718(3) 0.5789(3) 0.0478(7) Uani d . 1 . .
H H1 0.4955 0.6056 0.5512 0.057 Uiso calc R 1 . .
C C2 0.4929(5) 0.7087(3) 0.7015(3) 0.0552(8) Uani d . 1 . .
H H2 0.5405 0.6685 0.7531 0.066 Uiso calc R 1 . .
C C3 0.4483(5) 0.8047(3) 0.7442(3) 0.0530(8) Uani d . 1 . .
H H3 0.4651 0.8306 0.8253 0.064 Uiso calc R 1 . .
C C4 0.3759(4) 0.8639(3) 0.6632(3) 0.0426(7) Uani d . 1 . .
C C5 0.3258(5) 0.9656(3) 0.6993(3) 0.0494(8) Uani d . 1 . .
H H5 0.3370 0.9933 0.7789 0.059 Uiso calc R 1 . .
C C6 0.2628(4) 1.0217(3) 0.6203(3) 0.0432(7) Uani d . 1 . .
H H6 0.2320 1.0878 0.6462 0.052 Uiso calc R 1 . .
C C7 0.2427(4) 0.9811(2) 0.4973(3) 0.0369(6) Uani d . 1 . .
C C8 0.1782(4) 1.0353(3) 0.4106(3) 0.0449(7) Uani d . 1 . .
H H8 0.1465 1.1019 0.4327 0.054 Uiso calc R 1 . .
C C9 0.1613(5) 0.9916(3) 0.2938(3) 0.0489(7) Uani d . 1 . .
H H9 0.1163 1.0272 0.2365 0.059 Uiso calc R 1 . .
C C10 0.2122(4) 0.8929(3) 0.2614(3) 0.0464(7) Uani d . 1 . .
H H10 0.2014 0.8628 0.1822 0.056 Uiso calc R 1 . .
C C11 0.3581(4) 0.8207(2) 0.5431(3) 0.0361(6) Uani d . 1 . .
C C12 0.2910(3) 0.8807(2) 0.4601(3) 0.0342(6) Uani d . 1 . .
N N1 0.2759(3) 0.8421(2) 0.3436(2) 0.0389(5) Uani d . 1 . .
H H1A 0.3070 0.7780 0.3214 0.058 Uiso d R 1 . .
N N2 0.4023(3) 0.7248(2) 0.5005(2) 0.0423(6) Uani d . 1 . .
O O51 0.2373(14) 0.9245(9) -0.0266(9) 0.095(3) Uiso d P 0.40 . .
O O52 0.3445(8) 0.9208(5) -0.0130(5) 0.0779(14) Uiso d P 0.60 . .
O O61 -0.023(2) 0.9425(14) -0.0330(15) 0.103(5) Uiso d P 0.25 . .
O O62 0.022(2) 0.8996(14) -0.0653(14) 0.093(4) Uiso d P 0.25 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 C13 O1 . . 126.5(3) ?
O2 C13 C14 . . 121.8(3) ?
O1 C13 C14 . . 111.7(2) ?
C15 C14 C16 . 2_766 118.4(2) ?
C15 C14 C13 . . 120.4(2) ?
C16 C14 C13 2_766 . 121.2(2) ?
C16 C15 C14 . . 121.1(3) ?
C16 C15 Cl1 . . 119.9(2) ?
C14 C15 Cl1 . . 119.0(2) ?
C15 C16 C14 . 2_766 120.5(2) ?
C15 C16 Cl2 . . 120.6(2) ?
C14 C16 Cl2 2_766 . 118.9(2) ?
O4 C17 O3 . . 125.5(2) ?
O4 C17 C18 . . 117.9(2) ?
O3 C17 C18 . . 116.6(2) ?
C19 C18 C20 . 2_665 118.1(2) ?
C19 C18 C17 . . 121.1(2) ?
C20 C18 C17 2_665 . 120.8(2) ?
C18 C19 C20 . . 121.7(2) ?
C18 C19 Cl3 . . 118.7(2) ?
C20 C19 Cl3 . . 119.6(2) ?
C19 C20 C18 . 2_665 120.2(2) ?
C19 C20 Cl4 . . 120.9(2) ?
C18 C20 Cl4 2_665 . 118.85(19) ?
C13 O1 H1' . . 109.5 ?
N2 C1 C2 . . 124.3(3) ?
N2 C1 H1 . . 117.9 ?
C2 C1 H1 . . 117.9 ?
C3 C2 C1 . . 119.1(3) ?
C3 C2 H2 . . 120.4 ?
C1 C2 H2 . . 120.4 ?
C2 C3 C4 . . 119.0(3) ?
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C11 C4 C3 . . 116.9(3) ?
C11 C4 C5 . . 119.8(3) ?
C3 C4 C5 . . 123.3(3) ?
C6 C5 C4 . . 121.3(3) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C7 . . 120.8(3) ?
C5 C6 H6 . . 119.6 ?
C7 C6 H6 . . 119.6 ?
C8 C7 C12 . . 117.8(3) ?
C8 C7 C6 . . 123.7(3) ?
C12 C7 C6 . . 118.5(3) ?
C9 C8 C7 . . 120.9(3) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C8 C9 C10 . . 119.5(3) ?
C8 C9 H9 . . 120.3 ?
C10 C9 H9 . . 120.3 ?
N1 C10 C9 . . 120.0(3) ?
N1 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
N2 C11 C4 . . 124.0(3) ?
N2 C11 C12 . . 117.6(3) ?
C4 C11 C12 . . 118.4(2) ?
N1 C12 C7 . . 119.3(3) ?
N1 C12 C11 . . 119.6(2) ?
C7 C12 C11 . . 121.1(3) ?
C10 N1 C12 . . 122.6(2) ?
C10 N1 H1A . . 119.2 ?
C12 N1 H1A . . 118.2 ?
C1 N2 C11 . . 116.7(3) ?
O52 O51 O62 . . 167.4(13) ?
O62 O61 O61 . 2_575 139(3) ?
O61 O62 O51 . . 127(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C13 O2 . 1.200(4) ?
C13 O1 . 1.310(3) ?
C13 C14 . 1.512(4) ?
C14 C15 . 1.395(4) ?
C14 C16 2_766 1.400(4) ?
C15 C16 . 1.388(4) ?
C15 Cl1 . 1.727(3) ?
C16 C14 2_766 1.400(4) ?
C16 Cl2 . 1.724(3) ?
C17 O4 . 1.227(3) ?
C17 O3 . 1.273(3) ?
C17 C18 . 1.522(3) ?
C18 C19 . 1.389(4) ?
C18 C20 2_665 1.398(4) ?
C19 C20 . 1.395(4) ?
C19 Cl3 . 1.737(3) ?
C20 C18 2_665 1.398(4) ?
C20 Cl4 . 1.724(3) ?
O1 H1' . 0.8200 ?
C1 N2 . 1.314(4) ?
C1 C2 . 1.402(5) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.368(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.416(5) ?
C3 H3 . 0.9300 ?
C4 C11 . 1.403(4) ?
C4 C5 . 1.435(4) ?
C5 C6 . 1.347(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.427(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.401(4) ?
C7 C12 . 1.414(4) ?
C8 C9 . 1.368(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.397(4) ?
C9 H9 . 0.9300 ?
C10 N1 . 1.329(4) ?
C10 H10 . 0.9300 ?
C11 N2 . 1.364(3) ?
C11 C12 . 1.427(4) ?
C12 N1 . 1.364(4) ?
N1 H1A . 0.9000 ?
O51 O52 . 0.864(10) ?
O51 O62 . 1.603(18) ?
O61 O62 . 0.831(19) ?
O61 O61 2_575 1.33(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1' O3 . 0.82 1.74 2.550(3) 170 yes
N1 H1A O3 . 0.90 1.95 2.788(4) 154 yes
C6 H6 O2 2_676 0.93 2.56 3.413(5) 152 yes
C10 H10 O4 . 0.93 2.43 3.193(4) 139 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 C13 C14 C15 . . . . -89.7(4) ?
O1 C13 C14 C15 . . . . 90.7(3) ?
O2 C13 C14 C16 . . . 2_766 89.5(4) ?
O1 C13 C14 C16 . . . 2_766 -90.1(3) ?
C16 C14 C15 C16 2_766 . . . 1.3(5) ?
C13 C14 C15 C16 . . . . -179.5(2) ?
C16 C14 C15 Cl1 2_766 . . . -179.9(2) ?
C13 C14 C15 Cl1 . . . . -0.7(4) ?
C14 C15 C16 C14 . . . 2_766 -1.3(5) ?
Cl1 C15 C16 C14 . . . 2_766 179.9(2) ?
C14 C15 C16 Cl2 . . . . 179.0(2) ?
Cl1 C15 C16 Cl2 . . . . 0.3(3) ?
O4 C17 C18 C19 . . . . 77.1(3) ?
O3 C17 C18 C19 . . . . -103.6(3) ?
O4 C17 C18 C20 . . . 2_665 -100.9(3) ?
O3 C17 C18 C20 . . . 2_665 78.5(3) ?
C20 C18 C19 C20 2_665 . . . -0.3(4) ?
C17 C18 C19 C20 . . . . -178.3(2) ?
C20 C18 C19 Cl3 2_665 . . . 178.91(19) ?
C17 C18 C19 Cl3 . . . . 0.9(3) ?
C18 C19 C20 C18 . . . 2_665 0.3(4) ?
Cl3 C19 C20 C18 . . . 2_665 -178.9(2) ?
C18 C19 C20 Cl4 . . . . -178.0(2) ?
Cl3 C19 C20 Cl4 . . . . 2.8(3) ?
N2 C1 C2 C3 . . . . 1.0(5) ?
C1 C2 C3 C4 . . . . 0.1(5) ?
C2 C3 C4 C11 . . . . -1.2(5) ?
C2 C3 C4 C5 . . . . -179.7(3) ?
C11 C4 C5 C6 . . . . -0.5(5) ?
C3 C4 C5 C6 . . . . 177.9(3) ?
C4 C5 C6 C7 . . . . 0.4(5) ?
C5 C6 C7 C8 . . . . -179.9(3) ?
C5 C6 C7 C12 . . . . -0.2(4) ?
C12 C7 C8 C9 . . . . 0.6(4) ?
C6 C7 C8 C9 . . . . -179.7(3) ?
C7 C8 C9 C10 . . . . -1.2(5) ?
C8 C9 C10 N1 . . . . 0.2(5) ?
C3 C4 C11 N2 . . . . 1.5(4) ?
C5 C4 C11 N2 . . . . 180.0(3) ?
C3 C4 C11 C12 . . . . -178.1(3) ?
C5 C4 C11 C12 . . . . 0.4(4) ?
C8 C7 C12 N1 . . . . 1.0(4) ?
C6 C7 C12 N1 . . . . -178.8(2) ?
C8 C7 C12 C11 . . . . 179.9(2) ?
C6 C7 C12 C11 . . . . 0.1(4) ?
N2 C11 C12 N1 . . . . -0.9(4) ?
C4 C11 C12 N1 . . . . 178.7(2) ?
N2 C11 C12 C7 . . . . -179.8(2) ?
C4 C11 C12 C7 . . . . -0.2(4) ?
C9 C10 N1 C12 . . . . 1.4(5) ?
C7 C12 N1 C10 . . . . -2.0(4) ?
C11 C12 N1 C10 . . . . 179.1(3) ?
C2 C1 N2 C11 . . . . -0.8(5) ?
C4 C11 N2 C1 . . . . -0.5(4) ?
C12 C11 N2 C1 . . . . 179.1(3) ?
O61 O61 O62 O51 2_575 . . . 24(6) ?
O52 O51 O62 O61 . . . . 155(5) ?
