#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:26:43 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179631 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/95/4509510.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4509510
loop_
_publ_author_name
'Boldog, Ishtvan'
'Daran, Jean-Claude'
'Chernega, Alexander N.'
'Rusanov, Eduard B.'
'Krautscheid, Harald'
'Domasevitch, Konstantin V.'
_publ_section_title
;
 Hydrogen Bonding Patterns and Supramolecular Structure of
 4,4′-Bipyrazolium Salts
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2895
_journal_paper_doi               10.1021/cg9002109
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         '3(C6 H8 N4), 6(I O3),  2(H I O3), 2(H2 O)'
_chemical_formula_sum            'C18 H26 I8 N12 O26'
_chemical_formula_weight         1841.7
_chemical_name_systematic
; 
4,4'-bipyrazolium iodate(V), 3:1:1 adduct with iodic acid and water 
;
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.15(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.923(2)
_cell_length_b                   20.399(4)
_cell_length_c                   10.364(2)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.8
_cell_measurement_theta_min      10.0
_cell_volume                     2081.6(7)
_computing_cell_refinement       'Stoe DIF4'
_computing_data_collection       'Stoe DIF4'
_computing_data_reduction        'Stoe REDU4'
_computing_molecular_graphics    'Diamond 2.1c (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Stoe Stadi 4'
_diffrn_measurement_method       'non-profiled ω-2θ 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  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4741
_diffrn_reflns_theta_full        27.05
_diffrn_reflns_theta_max         27.05
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    6.067
_exptl_absorpt_correction_T_max  0.33625
_exptl_absorpt_correction_T_min  0.26341
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.938
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1700
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.796
_refine_diff_density_min         -1.462
_refine_diff_density_rms         0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0436P)²+0.0917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0713
_reflns_number_gt                3731
_reflns_number_total             4668
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg9002109sup1.cif
_cod_data_source_block           (11)
_cod_original_sg_symbol_H-M      'P 2(1)/m'
_cod_database_code               4509510
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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
I2 I 0.37814(3) 0.567275(15) 0.95223(3) 0.01756(8) Uani 1 d .
O4 O 0.3573(4) 0.65530(18) 0.9276(3) 0.0272(8) Uani 1 d .
O5 O 0.2934(4) 0.56095(19) 1.0962(3) 0.0280(8) Uani 1 d .
O6 O 0.5531(3) 0.56608(18) 1.0273(3) 0.0254(8) Uani 1 d .
N1 N 0.0252(4) 0.7175(2) 1.9357(4) 0.0237(9) Uani 1 d .
H1 H 0.0232 0.6932 2.0033 0.028 Uiso 1 calc R
N2 N 0.0242(4) 0.7171(2) 1.3881(4) 0.0236(9) Uani 1 d .
H2 H 0.0223 0.6927 1.3202 0.028 Uiso 1 calc R
N3 N -0.2989(4) 0.7174(2) 1.6111(4) 0.0242(9) Uani 1 d .
H3 H -0.2961 0.6929 1.6790 0.029 Uiso 1 calc R
N4 N -0.3156(5) 0.7176(2) 1.0631(4) 0.0313(10) Uani 1 d .
H4 H -0.3170 0.6932 0.9952 0.038 Uiso 1 calc R
N5 N 0.3760(4) 0.7173(2) 1.7041(4) 0.0243(9) Uani 1 d .
H5 H 0.3796 0.6929 1.7721 0.029 Uiso 1 calc R
N6 N 0.3404(4) 0.7173(2) 1.1537(4) 0.0241(9) Uani 1 d .
H6 H 0.3364 0.6930 1.0855 0.029 Uiso 1 calc R
C1 C 0.0287(5) 0.6954(3) 1.8144(4) 0.0232(10) Uani 1 d .
H1A H 0.0307 0.6518 1.7889 0.028 Uiso 1 calc R
C2 C 0.0287(7) 0.7500 1.7338(6) 0.0175(13) Uani 1 d S
C3 C 0.0288(6) 0.7500 1.5922(6) 0.0183(13) Uani 1 d S
C4 C 0.0277(5) 0.6957(3) 1.5097(4) 0.0214(10) Uani 1 d .
H4A H 0.0292 0.6520 1.5355 0.026 Uiso 1 calc R
C5 C -0.3038(5) 0.6959(3) 1.4890(4) 0.0245(11) Uani 1 d .
H5A H -0.3045 0.6523 1.4629 0.029 Uiso 1 calc R
C6 C -0.3079(7) 0.7500 1.4080(6) 0.0192(13) Uani 1 d S
C7 C -0.3111(7) 0.7500 1.2667(6) 0.0196(13) Uani 1 d S
C8 C -0.3131(6) 0.6960(3) 1.1841(4) 0.0312(12) Uani 1 d .
H8A H -0.3127 0.6522 1.2094 0.037 Uiso 1 calc R
C9 C 0.3694(5) 0.6957(3) 1.5818(4) 0.0233(10) Uani 1 d .
H9A H 0.3689 0.6521 1.5559 0.028 Uiso 1 calc R
C10 C 0.3634(7) 0.7500 1.4998(6) 0.0195(13) Uani 1 d S
C11 C 0.3530(7) 0.7500 1.3571(6) 0.0176(13) Uani 1 d S
C12 C 0.3476(5) 0.6955(3) 1.2752(4) 0.0237(10) Uani 1 d .
H12A H 0.3489 0.6518 1.3010 0.028 Uiso 1 calc R
I1 I 0.00756(3) 0.561803(15) 2.13234(3) 0.01701(8) Uani 1 d .
O1 O 0.0106(4) 0.65013(18) 2.1623(3) 0.0262(8) Uani 1 d .
O2 O -0.1601(4) 0.5409(2) 2.1692(3) 0.0283(8) Uani 1 d .
O3 O -0.0227(4) 0.56717(18) 1.9567(3) 0.0260(8) Uani 1 d .
I3 I -0.29670(3) 0.572269(15) 0.82385(3) 0.02017(8) Uani 1 d .
O7 O -0.2906(4) 0.66131(17) 0.8400(3) 0.0270(8) Uani 1 d .
O8 O -0.4670(4) 0.5645(2) 0.7459(4) 0.0326(9) Uani 1 d .
O9 O -0.2018(4) 0.5664(2) 0.6855(4) 0.0337(9) Uani 1 d .
O10 O -0.1815(4) 0.4449(2) 0.3406(4) 0.0284(8) Uani 1 d .
I4 I -0.18921(3) 0.489805(15) 0.50219(3) 0.01878(8) Uani 1 d .
O11 O -0.0439(4) 0.45006(19) 0.5890(3) 0.0268(8) Uani 1 d .
O12 O -0.3195(4) 0.4408(2) 0.5548(4) 0.0336(9) Uani 1 d .
O20 O -0.5843(5) 0.4413(2) 0.6393(5) 0.0515(13) Uani 1 d .
H10 H -0.193(9) 0.473(5) 0.287(8) 0.07(3) Uiso 1 d .
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'
I I -0.4742 1.8119 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O5 I2 O6 99.44(17) . .
O5 I2 O4 97.44(16) . .
O6 I2 O4 99.18(17) . .
N1 N1 C1 109.7(3) 4_575 .
N1 N1 H1 125.2 4_575 .
C1 N1 H1 125.2 . .
C4 N2 N2 109.2(3) . 4_575
C4 N2 H2 125.4 . .
N2 N2 H2 125.4 4_575 .
N3 N3 C5 109.2(3) 4_575 .
N3 N3 H3 125.4 4_575 .
C5 N3 H3 125.4 . .
N4 N4 C8 109.4(3) 4_575 .
N4 N4 H4 125.3 4_575 .
C8 N4 H4 125.3 . .
N5 N5 C9 109.3(3) 4_575 .
N5 N5 H5 125.4 4_575 .
C9 N5 H5 125.4 . .
C12 N6 N6 109.6(3) . 4_575
C12 N6 H6 125.2 . .
N6 N6 H6 125.2 4_575 .
N1 C1 C2 107.2(5) . .
N1 C1 H1A 126.4 . .
C2 C1 H1A 126.4 . .
C1 C2 C1 106.2(6) 4_575 .
C1 C2 C3 126.9(3) 4_575 .
C1 C2 C3 126.9(3) . .
C4 C3 C4 104.8(6) 4_575 .
C4 C3 C2 127.6(3) 4_575 .
C4 C3 C2 127.6(3) . .
N2 C4 C3 108.5(5) . .
N2 C4 H4A 125.8 . .
C3 C4 H4A 125.8 . .
N3 C5 C6 107.9(5) . .
N3 C5 H5A 126.0 . .
C6 C5 H5A 126.0 . .
C5 C6 C5 105.8(6) 4_575 .
C5 C6 C7 127.1(3) 4_575 .
C5 C6 C7 127.1(3) . .
C8 C7 C8 104.4(6) 4_575 .
C8 C7 C6 127.8(3) 4_575 .
C8 C7 C6 127.8(3) . .
N4 C8 C7 108.4(5) . .
N4 C8 H8A 125.8 . .
C7 C8 H8A 125.8 . .
N5 C9 C10 108.1(5) . .
N5 C9 H9A 126.0 . .
C10 C9 H9A 126.0 . .
C9 C10 C9 105.3(6) 4_575 .
C9 C10 C11 127.3(3) 4_575 .
C9 C10 C11 127.3(3) . .
C12 C11 C12 105.7(6) 4_575 .
C12 C11 C10 127.2(3) 4_575 .
C12 C11 C10 127.2(3) . .
N6 C12 C11 107.6(5) . .
N6 C12 H12A 126.2 . .
C11 C12 H12A 126.2 . .
O2 I1 O3 100.67(17) . .
O2 I1 O1 101.16(17) . .
O3 I1 O1 96.22(15) . .
O8 I3 O9 101.06(18) . .
O8 I3 O7 98.56(18) . .
O9 I3 O7 97.08(17) . .
I3 O9 I4 136.8(2) . .
I4 O10 H10 104(6) . .
O12 I4 O11 99.35(19) . .
O12 I4 O10 96.24(18) . .
O11 I4 O10 96.02(17) . .
O12 I4 O9 90.69(16) . .
O11 I4 O9 90.84(15) . .
O10 I4 O9 169.33(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I2 O5 1.806(3) .
I2 O6 1.812(3) .
I2 O4 1.822(4) .
N1 N1 1.325(9) 4_575
N1 C1 1.340(6) .
N1 H1 0.8600 .
N2 C4 1.331(6) .
N2 N2 1.342(9) 4_575
N2 H2 0.8600 .
N3 N3 1.331(9) 4_575
N3 C5 1.334(6) .
N3 H3 0.8600 .
N4 N4 1.322(10) 4_575
N4 C8 1.327(6) .
N4 H4 0.8600 .
N5 N5 1.333(8) 4_575
N5 C9 1.336(6) .
N5 H5 0.8600 .
N6 C12 1.330(6) .
N6 N6 1.333(8) 4_575
N6 H6 0.8600 .
C1 C2 1.392(6) .
C1 H1A 0.9300 .
C2 C1 1.392(6) 4_575
C2 C3 1.468(8) .
C3 C4 1.398(6) 4_575
C3 C4 1.398(6) .
C4 H4A 0.9300 .
C5 C6 1.384(6) .
C5 H5A 0.9300 .
C6 C5 1.384(6) 4_575
C6 C7 1.460(8) .
C7 C8 1.395(6) 4_575
C7 C8 1.395(6) .
C8 H8A 0.9300 .
C9 C10 1.392(6) .
C9 H9A 0.9300 .
C10 C9 1.392(6) 4_575
C10 C11 1.470(8) .
C11 C12 1.396(6) 4_575
C11 C12 1.396(6) .
C12 H12A 0.9300 .
I1 O2 1.804(4) .
I1 O3 1.811(3) .
I1 O1 1.828(4) .
I3 O8 1.787(4) .
I3 O9 1.815(3) .
I3 O7 1.824(4) .
O9 I4 2.476(4) .
O10 I4 1.919(4) .
O10 H10 0.79(9) .
I4 O12 1.774(4) .
I4 O11 1.795(4) .
