#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/52/2225266.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_2225266
loop_
_publ_author_name
'Marouani, Houda'
'Rzaigui, Mohamed'
'Al-Deyab, Salem S.'
_publ_section_title
;
 Bis(oxonium) tetrakis(o-toluidinium) cyclohexaphosphate
;
_journal_coeditor_code           HB5337
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o702
_journal_paper_doi               10.1107/S1600536810006537
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '4C7 H10 N +, 2H3 O +, P6 O18 6-'
_chemical_formula_moiety         '4(C7 H10 N +), 2(H3 O +), P6 O18 6-'
_chemical_formula_sum            'C28 H46 N4 O20 P6'
_chemical_formula_weight         944.51
_chemical_name_systematic
;
Bis(oxonium) tetrakis(o-toluidinium) cyclohexaphosphate
;
_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                95.35(4)
_cell_angle_beta                 92.23(3)
_cell_angle_gamma                116.00(5)
_cell_formula_units_Z            1
_cell_length_a                   9.344(3)
_cell_length_b                   10.360(2)
_cell_length_c                   11.537(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      12
_cell_measurement_theta_min      10
_cell_volume                     995.4(6)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1996)'
_computing_molecular_graphics    'Ortep-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'non-profiled 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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0964
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6038
_diffrn_reflns_theta_full        29.97
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        10
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.381
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         5773
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1388
_refine_ls_R_factor_gt           0.0517
_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)+(0.0495P)²+0.1583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                3061
_reflns_number_total             5773
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5337.cif
_cod_data_source_block           I
_cod_original_cell_volume        995.4(4)
_cod_database_code               2225266
_cod_database_fobs_code          2225266
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
P P1 0.19977(8) -0.14917(7) 0.55334(6) 0.02334(15) Uani d . 1 . .
P P2 -0.14713(8) -0.25078(7) 0.56200(6) 0.02236(15) Uani d . 1 . .
P P3 0.28988(8) 0.16136(7) 0.62215(6) 0.02600(16) Uani d . 1 . .
O O1 0.2843(2) -0.2032(2) 0.62940(17) 0.0356(5) Uani d . 1 . .
O O2 0.1635(2) -0.2086(2) 0.42722(15) 0.0313(4) Uani d . 1 . .
O O3 0.2961(2) 0.0217(2) 0.55757(19) 0.0398(5) Uani d . 1 . .
O O4 0.0375(2) -0.1674(2) 0.60834(15) 0.0285(4) Uani d . 1 . .
O O5 -0.2360(2) -0.2181(2) 0.65479(16) 0.0306(4) Uani d . 1 . .
O O6 -0.1935(2) -0.40394(19) 0.51838(17) 0.0372(5) Uani d . 1 . .
O O7 -0.1447(2) -0.1662(2) 0.45304(16) 0.0293(4) Uani d . 1 . .
O O8 0.2395(2) 0.1384(2) 0.74021(16) 0.0401(5) Uani d . 1 . .
O O9 0.4383(2) 0.2884(2) 0.6012(2) 0.0453(6) Uani d . 1 . .
O O10 0.7313(2) 0.3898(2) 0.64060(18) 0.0321(4) Uani d D 1 . .
N N1 0.9215(3) 0.0733(2) 0.74960(18) 0.0291(5) Uani d . 1 . .
H H1A 1.0242 0.0929 0.7486 0.044 Uiso calc R 1 . .
H H1B 0.8992 0.1265 0.7023 0.044 Uiso calc R 1 . .
H H1C 0.8609 -0.0201 0.7255 0.044 Uiso calc R 1 . .
N N2 0.4244(3) 0.6264(2) 0.6809(2) 0.0320(5) Uani d . 1 . .
H H2A 0.3811 0.5381 0.6413 0.048 Uiso calc R 1 . .
H H2B 0.5279 0.6711 0.6701 0.048 Uiso calc R 1 . .
H H2C 0.3755 0.6766 0.6555 0.048 Uiso calc R 1 . .
C C1 0.8890(3) 0.1076(3) 0.8692(2) 0.0269(5) Uani d . 1 . .
C C2 0.7377(3) 0.0942(3) 0.8895(2) 0.0303(6) Uani d . 1 . .
C C3 0.7148(4) 0.1246(3) 1.0057(3) 0.0382(7) Uani d . 1 . .
H H3 0.6155 0.1174 1.0236 0.046 Uiso calc R 1 . .
C C4 0.8337(4) 0.1648(3) 1.0948(3) 0.0428(8) Uani d . 1 . .
H H4 0.8136 0.1824 1.1715 0.051 Uiso calc R 1 . .
C C5 0.9816(4) 0.1791(4) 1.0705(3) 0.0453(8) Uani d . 1 . .
H H5 1.0629 0.2084 1.1304 0.054 Uiso calc R 1 . .
C C6 1.0098(4) 0.1498(3) 0.9566(3) 0.0392(7) Uani d . 1 . .
H H6 1.1098 0.1585 0.9394 0.047 Uiso calc R 1 . .
C C7 0.6060(4) 0.0507(4) 0.7933(3) 0.0455(8) Uani d . 1 . .
H H7A 0.6445 0.1115 0.7325 0.068 Uiso calc R 1 . .
H H7B 0.5172 0.0613 0.8240 0.068 Uiso calc R 1 . .
H H7C 0.5724 -0.0484 0.7620 0.068 Uiso calc R 1 . .
C C8 0.4056(3) 0.6151(3) 0.8077(2) 0.0311(6) Uani d . 1 . .
C C9 0.2550(4) 0.5396(3) 0.8433(3) 0.0357(7) Uani d . 1 . .
C C10 0.2453(4) 0.5348(3) 0.9631(3) 0.0445(8) Uani d . 1 . .
H H10 0.1461 0.4832 0.9906 0.053 Uiso calc R 1 . .
C C11 0.3771(5) 0.6038(4) 1.0416(3) 0.0489(8) Uani d . 1 . .
H H11 0.3667 0.5987 1.1211 0.059 Uiso calc R 1 . .
C C12 0.5246(4) 0.6802(4) 1.0034(3) 0.0536(9) Uani d . 1 . .
H H12 0.6139 0.7282 1.0571 0.064 Uiso calc R 1 . .
C C13 0.5409(4) 0.6862(3) 0.8859(3) 0.0414(7) Uani d . 1 . .
H H13 0.6408 0.7370 0.8592 0.050 Uiso calc R 1 . .
C C14 0.1088(4) 0.4694(4) 0.7588(3) 0.0517(9) Uani d . 1 . .
H H14A 0.0923 0.5425 0.7232 0.078 Uiso calc R 1 . .
H H14B 0.0177 0.4154 0.7996 0.078 Uiso calc R 1 . .
H H14C 0.1226 0.4054 0.6995 0.078 Uiso calc R 1 . .
H H110 0.6282(11) 0.348(3) 0.633(3) 0.057(11) Uiso d D 1 . .
H H210 0.770(4) 0.331(3) 0.617(3) 0.088(15) Uiso d D 1 . .
H H310 0.767(4) 0.464(2) 0.603(3) 0.079(14) Uiso d D 1 . .
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 -2 2
4 2 -2
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
O1 P1 O2 . . 118.49(11) ?
O1 P1 O3 . . 110.27(13) ?
O2 P1 O3 . . 106.30(12) ?
O1 P1 O4 . . 108.90(11) ?
O2 P1 O4 . . 109.44(11) ?
O3 P1 O4 . . 102.21(11) ?
O6 P2 O5 . . 118.69(12) ?
O6 P2 O7 . . 108.57(12) ?
O5 P2 O7 . . 110.85(11) ?
O6 P2 O4 . . 111.40(12) ?
O5 P2 O4 . . 106.38(11) ?
O7 P2 O4 . . 99.21(11) ?
O8 P3 O9 . . 121.31(13) ?
O8 P3 O3 . . 111.13(13) ?
O9 P3 O3 . . 107.21(12) ?
O8 P3 O7 . 2_556 106.23(11) ?
O9 P3 O7 . 2_556 107.42(12) ?
O3 P3 O7 . 2_556 101.72(12) ?
P3 O3 P1 . . 137.49(13) ?
P2 O4 P1 . . 133.83(12) ?
P2 O7 P3 . 2_556 129.82(12) ?
H110 O10 H210 . . 112(2) ?
H110 O10 H310 . . 110(2) ?
H210 O10 H310 . . 110(2) ?
C1 N1 H1A . . 109.5 ?
C1 N1 H1B . . 109.5 ?
H1A N1 H1B . . 109.5 ?
C1 N1 H1C . . 109.5 ?
H1A N1 H1C . . 109.5 ?
H1B N1 H1C . . 109.5 ?
C8 N2 H2A . . 109.5 ?
C8 N2 H2B . . 109.5 ?
H2A N2 H2B . . 109.5 ?
C8 N2 H2C . . 109.5 ?
H2A N2 H2C . . 109.5 ?
H2B N2 H2C . . 109.5 ?
C6 C1 C2 . . 122.8(3) ?
C6 C1 N1 . . 118.0(2) ?
C2 C1 N1 . . 119.1(2) ?
C1 C2 C3 . . 115.7(3) ?
C1 C2 C7 . . 122.8(3) ?
C3 C2 C7 . . 121.5(3) ?
C4 C3 C2 . . 122.3(3) ?
C4 C3 H3 . . 118.8 ?
C2 C3 H3 . . 118.8 ?
C5 C4 C3 . . 120.0(3) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 119.7(3) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C1 C6 C5 . . 119.4(3) ?
C1 C6 H6 . . 120.3 ?
C5 C6 H6 . . 120.3 ?
C2 C7 H7A . . 109.5 ?
C2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C9 C8 C13 . . 122.6(3) ?
C9 C8 N2 . . 119.2(2) ?
C13 C8 N2 . . 118.2(3) ?
C8 C9 C10 . . 116.4(3) ?
C8 C9 C14 . . 122.2(3) ?
C10 C9 C14 . . 121.4(3) ?
C11 C10 C9 . . 122.0(3) ?
C11 C10 H10 . . 119.0 ?
C9 C10 H10 . . 119.0 ?
C10 C11 C12 . . 120.2(3) ?
C10 C11 H11 . . 119.9 ?
C12 C11 H11 . . 119.9 ?
C11 C12 C13 . . 120.1(3) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C12 C13 C8 . . 118.8(3) ?
C12 C13 H13 . . 120.6 ?
C8 C13 H13 . . 120.6 ?
C9 C14 H14A . . 109.5 ?
C9 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C9 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
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
P1 O1 . 1.461(2) ?
P1 O2 . 1.491(2) ?
P1 O3 . 1.591(2) ?
P1 O4 . 1.6075(19) ?
P2 O6 . 1.480(2) ?
P2 O5 . 1.4830(19) ?
P2 O7 . 1.5931(19) ?
P2 O4 . 1.594(2) ?
P3 O8 . 1.465(2) ?
P3 O9 . 1.483(2) ?
P3 O3 . 1.590(2) ?
P3 O7 2_556 1.6035(19) ?
O7 P3 2_556 1.6035(19) ?
O10 H110 . 0.862(10) ?
O10 H210 . 0.863(10) ?
O10 H310 . 0.864(10) ?
N1 C1 . 1.470(3) ?
N1 H1A . 0.8900 ?
N1 H1B . 0.8900 ?
N1 H1C . 0.8900 ?
N2 C8 . 1.489(3) ?
N2 H2A . 0.8900 ?
N2 H2B . 0.8900 ?
N2 H2C . 0.8900 ?
C1 C6 . 1.370(4) ?
C1 C2 . 1.390(4) ?
C2 C3 . 1.395(4) ?
C2 C7 . 1.504(4) ?
C3 C4 . 1.374(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.367(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.383(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 C9 . 1.378(4) ?
C8 C13 . 1.388(4) ?
C9 C10 . 1.393(4) ?
C9 C14 . 1.496(4) ?
C10 C11 . 1.367(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.369(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.375(5) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
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
O10 H110 O9 . 0.862(10) 1.616(12) 2.469(3) 170(3)
O10 H210 O2 2_656 0.863(10) 1.688(10) 2.550(3) 177(3)
O10 H310 O6 1_665 0.864(10) 1.668(12) 2.524(3) 171(3)
N1 H1A O8 1_655 0.89 1.86 2.753(3) 177.3
N1 H1B O2 2_656 0.89 1.98 2.853(3) 168.0
N1 H1C O5 1_655 0.89 1.92 2.800(3) 168.7
N2 H2A O6 2_556 0.89 2.35 3.085(4) 139.7
N2 H2B O5 1_665 0.89 2.02 2.904(3) 176.2
N2 H2C O1 1_565 0.89 1.83 2.710(3) 169.9
