#------------------------------------------------------------------------------
#$Date: 2016-02-14 15:26:36 +0100 (dom 14 de feb de 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/09/2220944.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_2220944
loop_
_publ_author_name
'Wu, Yi-Yi'
'Huang, Chun-De'
'Huang, Jie-Xuan'
'Zeng, Rong-Hua'
'Luo, Yi-Fan'
_publ_section_title
;
 Hemi(4,4'-bipyridinium) hexafluoridophosphate bis(4-aminobenzoic acid)
 4,4'-bipyridine monohydrate
;
_journal_coeditor_code           WN2299
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o278
_journal_paper_doi               10.1107/S1600536808043900
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac
'0.5C10 H10 N2 2+, P1 F6 -, C10 H8 N2, 2C7 H7 N O2, H2 O1'
_chemical_formula_moiety
'0.5(C10 H10 N2 2+), P1 F6 -, C10 H8 N2, 2(C7 H7 N O2), H2 O1'
_chemical_formula_sum            'C29 H29 F6 N5 O5 P'
_chemical_formula_weight         672.54
_chemical_name_systematic
;
Hemi(4,4'-bipyridinium) hexafluoridophosphate bis(4-aminobenzoic acid)
4,4'-bipyridine monohydrate
;
_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                92.5570(10)
_cell_angle_beta                 98.0630(10)
_cell_angle_gamma                117.3460(10)
_cell_formula_units_Z            2
_cell_length_a                   10.1032(2)
_cell_length_b                   10.1142(2)
_cell_length_c                   16.8906(3)
_cell_measurement_reflns_used    2023
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.47
_cell_measurement_theta_min      2.36
_cell_volume                     1506.23(5)
_computing_cell_refinement       'APEX2 (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'APEX2 (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0568
_diffrn_reflns_av_sigmaI/netI    0.0678
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22618
_diffrn_reflns_theta_full        27.93
_diffrn_reflns_theta_max         27.93
_diffrn_reflns_theta_min         2.28
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             694
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.335
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         7121
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1560
_refine_ls_R_factor_gt           0.0658
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0875P)²+0.1722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1581
_refine_ls_wR_factor_ref         0.2053
_reflns_number_gt                3129
_reflns_number_total             7121
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2299.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C29 H29 F6 N5 O5 P1'
_cod_database_code               2220944
_cod_database_fobs_code          2220944
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 C1 0.4034(4) 0.5337(4) 0.7188(2) 0.0650(9) Uani d . 1 A 5
C C2 0.4778(4) 0.5250(4) 0.7922(2) 0.0656(9) Uani d . 1 A 5
H H2 0.5740 0.5331 0.7960 0.079 Uiso calc R 1 A 5
C C3 0.4122(4) 0.5047(4) 0.8589(2) 0.0602(9) Uani d . 1 A 5
H H3 0.4645 0.4991 0.9075 0.072 Uiso calc R 1 A 5
C C4 0.2682(3) 0.4922(3) 0.8557(2) 0.0523(8) Uani d . 1 A 5
C C5 0.1957(4) 0.4726(3) 0.9266(2) 0.0576(8) Uani d . 1 A 5
C C6 0.1930(4) 0.4994(3) 0.7822(2) 0.0590(8) Uani d . 1 A 5
H H6 0.0961 0.4896 0.7783 0.071 Uiso calc R 1 A 5
C C7 0.2589(4) 0.5208(4) 0.7152(2) 0.0646(9) Uani d . 1 A 5
H H7 0.2068 0.5267 0.6666 0.077 Uiso calc R 1 A 5
C C8 0.8336(4) 0.1574(4) 0.3481(2) 0.0662(9) Uani d . 1 B 5
H H8 0.8482 0.2431 0.3790 0.079 Uiso calc R 1 B 5
C C9 0.9268(4) 0.1700(4) 0.2940(2) 0.0627(9) Uani d . 1 B 5
H H9 1.0027 0.2642 0.2880 0.075 Uiso calc R 1 B 5
C C10 0.9095(3) 0.0437(3) 0.24786(18) 0.0503(7) Uani d . 1 B 5
C C11 1.0119(4) 0.0620(4) 0.19048(19) 0.0555(8) Uani d . 1 B 5
C C12 0.7954(3) -0.0956(4) 0.25815(19) 0.0545(8) Uani d . 1 B 5
H H12 0.7825 -0.1815 0.2283 0.065 Uiso calc R 1 B 5
C C13 0.7011(4) -0.1079(4) 0.31200(19) 0.0579(8) Uani d . 1 B 5
H H13 0.6254 -0.2022 0.3180 0.070 Uiso calc R 1 B 5
C C14 0.7174(4) 0.0183(4) 0.35751(19) 0.0578(8) Uani d . 1 B 5
N N3 0.1693(3) -0.0235(3) 1.04268(16) 0.0592(7) Uani d . 1 C 5
C C16 0.2657(5) 0.1119(4) 1.0271(2) 0.0754(11) Uani d . 1 C 5
H H16 0.2693 0.1953 1.0549 0.090 Uiso calc R 1 C 5
C C17 0.3601(4) 0.1349(4) 0.9723(2) 0.0682(10) Uani d . 1 C 5
H H17 0.4246 0.2321 0.9634 0.082 Uiso calc R 1 C 5
C C18 0.3597(3) 0.0145(3) 0.93018(17) 0.0464(7) Uani d . 1 C 5
C C19 0.2589(3) -0.1253(4) 0.9462(2) 0.0606(9) Uani d . 1 C 5
H H19 0.2522 -0.2109 0.9192 0.073 Uiso calc R 1 C 5
C C20 0.1679(4) -0.1388(4) 1.0023(2) 0.0650(9) Uani d . 1 C 5
H H20 0.1018 -0.2346 1.0122 0.078 Uiso calc R 1 C 5
C C21 0.4624(3) 0.0328(3) 0.87181(17) 0.0452(7) Uani d . 1 C 5
C C22 0.5692(4) 0.1715(4) 0.8566(2) 0.0641(9) Uani d . 1 C 5
H H22 0.5793 0.2585 0.8839 0.077 Uiso calc R 1 C 5
C C23 0.6600(4) 0.1817(4) 0.8017(2) 0.0662(9) Uani d . 1 C 5
H H23 0.7302 0.2765 0.7925 0.079 Uiso calc R 1 C 5
N N4 0.6522(3) 0.0623(3) 0.76098(15) 0.0576(7) Uani d . 1 C 5
C C25 0.5513(5) -0.0691(4) 0.7747(2) 0.0791(11) Uani d . 1 C 5
H H25 0.5432 -0.1540 0.7460 0.095 Uiso calc R 1 C 5
C C26 0.4564(4) -0.0888(4) 0.8291(2) 0.0734(11) Uani d . 1 C 5
H H26 0.3877 -0.1852 0.8369 0.088 Uiso calc R 1 C 5
N N5 0.8058(3) 0.0432(3) 0.64624(16) 0.0600(7) Uani d . 1 D 5
H H27 0.7588 0.0538 0.6827 0.072 Uiso calc R 1 D 5
C C28 0.9248(4) 0.1591(4) 0.6303(2) 0.0761(11) Uani d . 1 D 5
H H28 0.9572 0.2528 0.6586 0.091 Uiso calc R 1 D 5
C C29 1.0029(4) 0.1461(4) 0.5730(2) 0.0719(10) Uani d . 1 D 5
H H29 1.0865 0.2306 0.5628 0.086 Uiso calc R 1 D 5
C C30 0.9587(3) 0.0097(3) 0.53068(17) 0.0481(7) Uani d . 1 . 5
C C31 0.8329(5) -0.1090(4) 0.5490(3) 0.0920(14) Uani d . 1 D 5
H H31 0.7977 -0.2044 0.5220 0.110 Uiso calc R 1 D 5
C C32 0.7592(5) -0.0883(5) 0.6064(3) 0.0932(13) Uani d . 1 D 5
H H32 0.6736 -0.1700 0.6172 0.112 Uiso calc R 1 D 5
F F3 0.4396(3) 0.6418(3) 0.46460(18) 0.1343(10) Uani d . 1 E 5
F F6 0.0964(3) 0.5330(3) 0.3961(2) 0.1465(12) Uani d . 1 E 5
N N1 0.4710(4) 0.5607(4) 0.6526(2) 0.0960(11) Uani d . 1 A 5
H H1A 0.5617 0.5727 0.6560 0.115 Uiso calc R 1 A 5
H H1B 0.4230 0.5658 0.6076 0.115 Uiso calc R 1 A 5
N N2 0.6215(3) 0.0068(4) 0.41031(18) 0.0812(9) Uani d . 1 B 5
H H2A 0.5499 -0.0797 0.4156 0.097 Uiso calc R 1 B 5
H H2B 0.6331 0.0860 0.4380 0.097 Uiso calc R 1 B 5
O O1 0.2766(3) 0.4659(3) 0.99380(15) 0.0756(7) Uani d . 1 A 5
H H1 0.2309 0.4589 1.0312 0.113 Uiso calc R 1 A 5
O O2 0.0709(3) 0.4645(3) 0.92571(15) 0.0767(7) Uani d . 1 A 5
O O3 0.9955(3) -0.0651(3) 0.15538(15) 0.0728(7) Uani d . 1 B 5
H H3A 1.0465 -0.0476 0.1197 0.109 Uiso calc R 1 B 5
O O4 1.1065(3) 0.1827(3) 0.17604(15) 0.0772(7) Uani d . 1 B 5
P P 0.26740(12) 0.58756(12) 0.43141(7) 0.0774(4) Uani d D 1 E 5
O O1W 0.1528(2) 0.4502(3) 0.12153(13) 0.0703(7) Uani d D 1 F 5
H H1W 0.0862 0.4708 0.1110 0.105 Uiso d RD 1 F 5
H H2W 0.1255 0.3604 0.1373 0.105 Uiso d RD 1 F 5
F F1 0.2698(15) 0.7215(12) 0.4737(9) 0.129(5) Uani d PDU 0.375(11) G 1
F F2 0.2105(13) 0.4994(17) 0.5008(6) 0.125(5) Uani d PDU 0.375(11) G 1
F F4 0.2560(8) 0.4439(8) 0.3880(8) 0.090(4) Uani d PDU 0.375(11) G 1
F F5 0.3176(16) 0.6648(13) 0.3621(5) 0.139(5) Uani d PDU 0.375(11) G 1
F F1' 0.3113(7) 0.7452(10) 0.4047(10) 0.192(6) Uani d PD 0.625(11) G 2
F F4' 0.2424(12) 0.4441(8) 0.4616(10) 0.222(6) Uani d PD 0.625(11) G 2
F F5' 0.2826(14) 0.534(2) 0.3497(4) 0.239(7) Uani d PD 0.625(11) G 2
F F2' 0.2667(13) 0.6511(18) 0.5141(5) 0.217(5) Uani d PD 0.625(11) G 2
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
N1 C1 C2 . . 121.3(3) ?
N1 C1 C7 . . 120.6(4) ?
C2 C1 C7 . . 118.0(3) ?
C3 C2 C1 . . 121.1(3) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C2 C3 C4 . . 121.2(3) ?
C2 C3 H3 . . 119.4 ?
C4 C3 H3 . . 119.4 ?
C6 C4 C3 . . 117.9(3) ?
C6 C4 C5 . . 119.7(3) ?
C3 C4 C5 . . 122.4(3) ?
O2 C5 O1 . . 121.4(3) ?
O2 C5 C4 . . 123.7(3) ?
O1 C5 C4 . . 115.0(3) ?
C7 C6 C4 . . 121.1(3) ?
C7 C6 H6 . . 119.5 ?
C4 C6 H6 . . 119.5 ?
C6 C7 C1 . . 120.8(3) ?
C6 C7 H7 . . 119.6 ?
C1 C7 H7 . . 119.6 ?
C9 C8 C14 . . 120.9(3) ?
C9 C8 H8 . . 119.5 ?
C14 C8 H8 . . 119.5 ?
C8 C9 C10 . . 120.9(3) ?
C8 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
C12 C10 C9 . . 118.3(3) ?
C12 C10 C11 . . 122.5(3) ?
C9 C10 C11 . . 119.2(3) ?
O4 C11 O3 . . 121.3(3) ?
O4 C11 C10 . . 124.2(3) ?
O3 C11 C10 . . 114.5(3) ?
C13 C12 C10 . . 120.8(3) ?
C13 C12 H12 . . 119.6 ?
C10 C12 H12 . . 119.6 ?
C12 C13 C14 . . 121.0(3) ?
C12 C13 H13 . . 119.5 ?
C14 C13 H13 . . 119.5 ?
N2 C14 C13 . . 121.2(3) ?
N2 C14 C8 . . 120.7(3) ?
C13 C14 C8 . . 118.1(3) ?
C20 N3 C16 . . 116.4(3) ?
N3 C16 C17 . . 123.5(3) ?
N3 C16 H16 . . 118.3 ?
C17 C16 H16 . . 118.3 ?
C16 C17 C18 . . 120.3(3) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
C19 C18 C17 . . 115.9(3) ?
C19 C18 C21 . . 121.5(3) ?
C17 C18 C21 . . 122.6(3) ?
C18 C19 C20 . . 120.2(3) ?
C18 C19 H19 . . 119.9 ?
C20 C19 H19 . . 119.9 ?
N3 C20 C19 . . 123.7(3) ?
N3 C20 H20 . . 118.1 ?
C19 C20 H20 . . 118.2 ?
C26 C21 C22 . . 115.6(3) ?
C26 C21 C18 . . 121.4(3) ?
C22 C21 C18 . . 123.0(3) ?
C23 C22 C21 . . 120.5(3) ?
C23 C22 H22 . . 119.7 ?
C21 C22 H22 . . 119.7 ?
N4 C23 C22 . . 122.8(3) ?
N4 C23 H23 . . 118.6 ?
C22 C23 H23 . . 118.6 ?
C25 N4 C23 . . 117.1(3) ?
N4 C25 C26 . . 123.6(3) ?
N4 C25 H25 . . 118.2 ?
C26 C25 H25 . . 118.2 ?
C21 C26 C25 . . 120.4(3) ?
C21 C26 H26 . . 119.8 ?
C25 C26 H26 . . 119.8 ?
C32 N5 C28 . . 119.5(3) ?
C32 N5 H27 . . 120.3 ?
C28 N5 H27 . . 120.3 ?
N5 C28 C29 . . 121.8(3) ?
N5 C28 H28 . . 119.1 ?
C29 C28 H28 . . 119.1 ?
C30 C29 C28 . . 120.5(3) ?
C30 C29 H29 . . 119.8 ?
C28 C29 H29 . . 119.8 ?
C29 C30 C31 . . 115.9(3) ?
C29 C30 C30 . 2_756 122.2(3) ?
C31 C30 C30 . 2_756 121.8(4) ?
C32 C31 C30 . . 120.7(4) ?
C32 C31 H31 . . 119.6 ?
C30 C31 H31 . . 119.6 ?
N5 C32 C31 . . 121.6(4) ?
N5 C32 H32 . . 119.2 ?
C31 C32 H32 . . 119.2 ?
C1 N1 H1A . . 120.0 ?
C1 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
C14 N2 H2A . . 120.0 ?
C14 N2 H2B . . 120.0 ?
H2A N2 H2B . . 120.0 ?
F6 P F3 . . 178.6(2) ?
H1W O1W H2W . . 115.1 ?
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
C1 N1 . 1.364(4) ?
C1 C2 . 1.387(5) ?
C1 C7 . 1.396(5) ?
C2 C3 . 1.361(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.394(4) ?
C3 H3 . 0.9300 ?
C4 C6 . 1.385(4) ?
C4 C5 . 1.465(4) ?
C5 O2 . 1.223(4) ?
C5 O1 . 1.325(4) ?
C6 C7 . 1.368(4) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.372(5) ?
C8 C14 . 1.392(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.391(4) ?
C9 H9 . 0.9300 ?
C10 C12 . 1.389(4) ?
C10 C11 . 1.472(4) ?
C11 O4 . 1.218(4) ?
C11 O3 . 1.318(4) ?
C12 C13 . 1.376(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.390(4) ?
C13 H13 . 0.9300 ?
C14 N2 . 1.377(4) ?
N3 C20 . 1.317(4) ?
N3 C16 . 1.331(4) ?
C16 C17 . 1.373(5) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.381(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.378(4) ?
C18 C21 . 1.487(4) ?
C19 C20 . 1.380(4) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C21 C26 . 1.370(4) ?
C21 C22 . 1.385(4) ?
C22 C23 . 1.368(4) ?
C22 H22 . 0.9300 ?
C23 N4 . 1.327(4) ?
C23 H23 . 0.9300 ?
N4 C25 . 1.306(4) ?
C25 C26 . 1.376(5) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
N5 C32 . 1.304(4) ?
N5 C28 . 1.310(4) ?
N5 H27 . 0.8600 ?
C28 C29 . 1.369(5) ?
C28 H28 . 0.9300 ?
C29 C30 . 1.367(4) ?
C29 H29 . 0.9300 ?
C30 C31 . 1.377(5) ?
C30 C30 2_756 1.477(6) ?
C31 C32 . 1.366(5) ?
C31 H31 . 0.9300 ?
C32 H32 . 0.9300 ?
F3 P . 1.570(3) ?
F6 P . 1.566(3) ?
N1 H1A . 0.8600 ?
N1 H1B . 0.8600 ?
N2 H2A . 0.8600 ?
N2 H2B . 0.8600 ?
O1 H1 . 0.8200 ?
O3 H3A . 0.8200 ?
O1W H1W . 0.7910 ?
O1W H2W . 0.8864 ?
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
O1W H2W O4 1_455 0.89 1.87 2.751(3) 169.4
O1W H1W O2 2_566 0.79 2.01 2.799(3) 173.5
O3 H3A N3 1_654 0.82 1.87 2.686(3) 173.5
O1 H1 O1W 1_556 0.82 1.80 2.617(3) 172.8
N1 H1B F3 . 0.86 2.57 3.324(4) 146.7
N5 H27 N4 . 0.86 1.84 2.700(4) 176.0
