#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/55/2225504.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_2225504
loop_
_publ_author_name
'Hemissi, Hanène'
'Rzaigui, Mohammed'
'Al-Deyab, Salem S.'
_publ_section_title
;
 Bis(3-ammoniomethylpyridinium) cyclotetraphosphate
;
_journal_coeditor_code           DN2541
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o779
_journal_page_last               o780
_journal_paper_doi               10.1107/S1600536810008056
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '2C6 H10 N2 2+ , P4 O12 4-'
_chemical_formula_moiety         '2(C6 H10 N2 2+), O12 P4 4-'
_chemical_formula_sum            'C12 H20 N4 O12 P4'
_chemical_formula_weight         536.20
_chemical_name_systematic
;
Bis(3-ammoniomethylpyridinium) cyclotetraphosphate
;
_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                113.24(2)
_cell_angle_beta                 98.73(3)
_cell_angle_gamma                108.76(3)
_cell_formula_units_Z            1
_cell_length_a                   7.849(2)
_cell_length_b                   8.384(2)
_cell_length_c                   9.448(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      10.65
_cell_measurement_theta_min      9.02
_cell_volume                     512.4(3)
_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 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_reflns_av_R_equivalents  0.0121
_diffrn_reflns_av_sigmaI/netI    0.0213
_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       15
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7923
_diffrn_reflns_theta_full        27.96
_diffrn_reflns_theta_max         27.96
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.471
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         5005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0490P)²+0.1514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                3963
_reflns_number_total             5005
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2541.cif
_cod_data_source_block           I
_cod_original_cell_volume        512.4(2)
_cod_database_code               2225504
_cod_database_fobs_code          2225504
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
O O4 0.14028(12) 0.17020(14) 0.16858(12) 0.02591(17) Uani d . 1 . .
O O2 0.20484(12) 0.04327(13) -0.08942(12) 0.02816(18) Uani d . 1 . .
O O1 0.07961(14) 0.30061(15) -0.02599(13) 0.03096(19) Uani d . 1 . .
O O3 0.41615(12) 0.37060(14) 0.12629(14) 0.0328(2) Uani d . 1 . .
O O5 -0.09804(14) 0.30451(14) 0.25390(12) 0.02842(18) Uani d . 1 . .
O O6 0.01424(14) 0.12073(17) 0.37735(13) 0.0330(2) Uani d . 1 . .
P P1 0.21242(4) 0.23999(4) 0.04410(4) 0.02125(7) Uani d . 1 . .
P P2 -0.03708(4) 0.15037(4) 0.23497(4) 0.02013(7) Uani d . 1 . .
N N2 0.71399(14) 0.34670(15) 1.01546(13) 0.02438(18) Uani d . 1 . .
H H2A 0.7405 0.3187 1.0954 0.037 Uiso calc R 1 . .
H H2B 0.6259 0.3920 1.0259 0.037 Uiso calc R 1 . .
H H2C 0.8188 0.4345 1.0204 0.037 Uiso calc R 1 . .
N N1 0.37134(15) 0.21366(16) 0.52122(14) 0.0284(2) Uani d . 1 . .
H H1 0.2559 0.1902 0.4771 0.034 Uiso calc R 1 . .
C C1 0.41069(16) 0.17716(18) 0.64460(16) 0.0259(2) Uani d . 1 . .
H H1A 0.3140 0.1291 0.6824 0.031 Uiso calc R 1 . .
C C4 0.6907(2) 0.3225(2) 0.53050(17) 0.0320(3) Uani d . 1 . .
H H4 0.7847 0.3727 0.4913 0.038 Uiso calc R 1 . .
C C6 0.64164(17) 0.17070(18) 0.85588(16) 0.0264(2) Uani d . 1 . .
H H6A 0.5287 0.0744 0.8515 0.032 Uiso calc R 1 . .
H H6B 0.7369 0.1203 0.8456 0.032 Uiso calc R 1 . .
C C2 0.59489(16) 0.21046(16) 0.71693(14) 0.02293(19) Uani d . 1 . .
C C5 0.5057(2) 0.28559(19) 0.46376(16) 0.0309(2) Uani d . 1 . .
H H5 0.4735 0.3106 0.3784 0.037 Uiso calc R 1 . .
C C3 0.73527(17) 0.28345(19) 0.65771(16) 0.0288(2) Uani d . 1 . .
H H3 0.8598 0.3064 0.7034 0.035 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.0667 0.0580 '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
2 3 -1
1 -5 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
P2 O4 P1 . . 136.26(6) ?
P2 O2 P1 2 . 134.03(6) ?
O1 P1 O3 . . 120.41(7) ?
O1 P1 O4 . . 110.99(6) ?
O3 P1 O4 . . 106.65(6) ?
O1 P1 O2 . . 111.42(7) ?
O3 P1 O2 . . 105.82(7) ?
O4 P1 O2 . . 99.36(6) ?
O5 P2 O6 . . 119.04(7) ?
O5 P2 O4 . . 112.23(6) ?
O6 P2 O4 . . 105.42(6) ?
O5 P2 O2 . 2 106.33(6) ?
O6 P2 O2 . 2 109.45(7) ?
O4 P2 O2 . 2 103.28(6) ?
C6 N2 H2A . . 109.5 ?
C6 N2 H2B . . 109.5 ?
H2A N2 H2B . . 109.5 ?
C6 N2 H2C . . 109.5 ?
H2A N2 H2C . . 109.5 ?
H2B N2 H2C . . 109.5 ?
C1 N1 C5 . . 122.18(11) ?
C1 N1 H1 . . 118.9 ?
C5 N1 H1 . . 118.9 ?
N1 C1 C2 . . 120.46(12) ?
N1 C1 H1A . . 119.8 ?
C2 C1 H1A . . 119.8 ?
C5 C4 C3 . . 118.82(13) ?
C5 C4 H4 . . 120.6 ?
C3 C4 H4 . . 120.6 ?
N2 C6 C2 . . 111.53(10) ?
N2 C6 H6A . . 109.3 ?
C2 C6 H6A . . 109.3 ?
N2 C6 H6B . . 109.3 ?
C2 C6 H6B . . 109.3 ?
H6A C6 H6B . . 108.0 ?
C3 C2 C1 . . 117.98(11) ?
C3 C2 C6 . . 120.87(11) ?
C1 C2 C6 . . 121.15(11) ?
N1 C5 C4 . . 120.20(12) ?
N1 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C2 C3 C4 . . 120.36(12) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
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
O4 P2 . 1.5992(10) ?
O4 P1 . 1.6057(10) ?
O2 P2 2 1.6044(14) ?
O2 P1 . 1.6085(11) ?
O1 P1 . 1.4766(10) ?
O3 P1 . 1.4781(12) ?
O5 P2 . 1.4739(10) ?
O6 P2 . 1.4824(10) ?
P2 O2 2 1.6044(14) ?
N2 C6 . 1.4894(18) ?
N2 H2A . 0.8900 ?
N2 H2B . 0.8900 ?
N2 H2C . 0.8900 ?
N1 C1 . 1.3345(17) ?
N1 C5 . 1.3393(19) ?
N1 H1 . 0.8600 ?
C1 C2 . 1.3875(17) ?
C1 H1A . 0.9300 ?
C4 C5 . 1.372(2) ?
C4 C3 . 1.389(2) ?
C4 H4 . 0.9300 ?
C6 C2 . 1.4990(17) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C2 C3 . 1.3875(18) ?
C5 H5 . 0.9300 ?
C3 H3 . 0.9300 ?
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
N1 H1 O6 . 0.8600 1.7700 2.6294(18) 175.00
N2 H2A O5 1_656 0.8900 1.8800 2.7079(17) 154.00
N2 H2B O3 1_556 0.8900 2.0200 2.7350(17) 137.00
N2 H2C O1 2_666 0.8900 2.0800 2.831(2) 141.00
C1 H1A O6 2_556 0.9300 2.5500 3.381(2) 149.00
C4 H4 O5 1_655 0.9300 2.4800 3.281(2) 144.00
C5 H5 O4 . 0.9300 2.6000 3.256(2) 128.00
C6 H6B O1 1_656 0.9700 2.4400 3.117(2) 127.00
