#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/15/2011586.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_2011586
loop_
_publ_author_name
'Ma, Guibin'
'Ilyukhin, Andrey'
'Glaser, Julius'
_publ_section_title
;
 2,2'-Bipyridinium bis(perchlorate)
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1473
_journal_page_last               1475
_journal_paper_doi               10.1107/S0108270100012452
_journal_volume                  56
_journal_year                    2000
_chemical_formula_iupac          'C10 H10 N2 2+, 2Cl O4 1-'
_chemical_formula_moiety         'C10 H10 N2 2+, 2Cl O4 1-'
_chemical_formula_sum            'C10 H10 Cl2 N2 O8'
_chemical_formula_weight         357.10
_chemical_name_common
;
2,2'-bipyridinium diperchlorate
;
_chemical_name_systematic
;
2,2'-bipyridinium diperchlorate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                97.974(19)
_cell_angle_beta                 98.50(2)
_cell_angle_gamma                108.63(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6042(8)
_cell_length_b                   9.0007(11)
_cell_length_c                   10.8647(16)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.0
_cell_measurement_theta_min      13.7
_cell_volume                     683.06(19)
_computing_cell_refinement       'CAD-4 VAX/PC'
_computing_data_collection       'CAD-4 VAX/PC (Enraf-Nonius, 1988)'
_computing_data_reduction        'JANA98 (Petricek & Dusek, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .000
_diffrn_reflns_av_sigmaI/netI    .0642
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2696
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        -3
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .520
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .1
_refine_diff_density_max         .297
_refine_diff_density_min         -.445
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    refine
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          .086
_refine_ls_R_factor_gt           .048
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0914P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .148
_reflns_number_gt                1811
_reflns_number_total             2696
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            av1046.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0914P)^2^] where P = (Fo^2^+2Fc^2^)/3' was changed
to 'calc'. New tag '_refine_ls_weighting_details' was created. The
value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0914P)^2^]
where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        683.07(15)
_cod_database_code               2011586
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
Cl1 .28745(12) .52491(9) .13366(8) .0343(2) Uani d . 1 . . Cl
Cl2 .19968(13) 1.04083(11) .37742(9) .0405(3) Uani d . 1 . . Cl
O1 .1115(4) .5413(3) .1554(3) .0548(8) Uani d . 1 . . O
O2 .4398(4) .6480(4) .2205(3) .0681(9) Uani d . 1 . . O
O3 .2914(5) .3757(3) .1544(4) .0764(11) Uani d . 1 . . O
O4 .3044(5) .5404(5) .0082(3) .0765(10) Uani d . 1 . . O
O5 .0948(5) 1.1438(4) .3636(3) .0742(10) Uani d . 1 . . O
O6 .0781(6) .8828(4) .3200(4) .0944(13) Uani d . 1 . . O
O7 .2660(5) 1.0497(4) .5089(3) .0631(9) Uani d . 1 . . O
O81 .358(3) 1.108(4) .323(3) .097(8) Uani d P .50 . . O
O82 .343(4) 1.050(5) .315(3) .144(13) Uani d P .50 . . O
N1 .1677(4) .7730(3) .8978(3) .0335(7) Uani d . 1 . . N
N2 .2367(4) .7546(4) .5796(3) .0341(7) Uani d . 1 . . N
C1 .1674(6) .8641(5) 1.0045(4) .0418(9) Uani d . 1 . . C
C2 .2400(5) 1.0272(4) 1.0200(4) .0396(9) Uani d . 1 . . C
C3 .3139(5) 1.0913(4) .9226(4) .0402(8) Uani d . 1 . . C
C4 .3177(5) .9932(4) .8144(3) .0344(8) Uani d . 1 . . C
C5 .2423(4) .8298(4) .8016(3) .0305(7) Uani d . 1 . . C
C6 .2424(4) .7133(4) .6948(3) .0275(7) Uani d . 1 . . C
C7 .2465(6) .6608(5) .4750(4) .0409(9) Uani d . 1 . . C
C8 .2582(5) .5136(4) .4809(3) .0384(8) Uani d . 1 . . C
C9 .2616(5) .4648(4) .5960(4) .0393(8) Uani d . 1 . . C
C10 .2562(5) .5653(4) .7045(4) .0355(8) Uani d . 1 . . C
H1 .117(6) .681(5) .892(4) .061(14) Uiso d . 1 . . H
H2 .113(5) .823(4) 1.069(4) .042(10) Uiso d . 1 . . H
H3 .234(5) 1.088(5) 1.094(4) .047(11) Uiso d . 1 . . H
H4 .383(5) 1.212(4) .938(3) .038(10) Uiso d . 1 . . H
H5 .355(5) 1.024(4) .728(3) .031(9) Uiso d . 1 . . H
H6 .227(5) .850(5) .572(4) .049(11) Uiso d . 1 . . H
H7 .235(5) .707(4) .395(4) .045(11) Uiso d . 1 . . H
H8 .287(5) .447(4) .407(3) .030(9) Uiso d . 1 . . H
H9 .268(5) .360(5) .592(4) .046(11) Uiso d . 1 . . H
H10 .256(5) .542(5) .784(4) .048(11) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .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
O3 Cl1 O4 110.5(2)
O3 Cl1 O2 109.2(2)
O4 Cl1 O2 109.6(2)
O3 Cl1 O1 109.61(19)
O4 Cl1 O1 109.3(2)
O2 Cl1 O1 108.62(19)
O82 Cl2 O5 120.0(15)
O82 Cl2 O6 99.1(18)
O5 Cl2 O6 108.0(2)
O82 Cl2 O81 20(3)
O5 Cl2 O81 103.5(14)
O6 Cl2 O81 117.0(16)
O82 Cl2 O7 109.6(14)
O5 Cl2 O7 109.6(2)
O6 Cl2 O7 109.9(2)
O81 Cl2 O7 108.5(10)
C1 N1 C5 124.2(3)
C1 N1 H1 115(3)
C5 N1 H1 121(3)
C7 N2 C6 123.5(3)
C7 N2 H6 118(3)
C6 N2 H6 119(3)
N1 C1 C2 119.9(3)
N1 C1 H2 123(2)
C2 C1 H2 117(2)
C1 C2 C3 118.0(3)
C1 C2 H3 118(3)
C3 C2 H3 124(3)
C4 C3 C2 120.6(3)
C4 C3 H4 121(2)
C2 C3 H4 118(2)
C5 C4 C3 119.8(3)
C5 C4 H5 110.4(18)
C3 C4 H5 129.2(18)
N1 C5 C4 117.4(3)
N1 C5 C6 117.2(3)
C4 C5 C6 125.4(3)
N2 C6 C10 118.0(3)
N2 C6 C5 117.9(3)
C10 C6 C5 124.1(3)
N2 C7 C8 120.1(3)
N2 C7 H7 114(2)
C8 C7 H7 126(2)
C7 C8 C9 118.7(3)
C7 C8 H8 121.9(19)
C9 C8 H8 118.6(19)
C8 C9 C10 120.5(3)
C8 C9 H9 114(2)
C10 C9 H9 126(2)
C6 C10 C9 119.2(3)
C6 C10 H10 114(2)
C9 C10 H10 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
Cl1 O3 . 1.401(3) ?
Cl1 O4 . 1.410(3) ?
Cl1 O2 . 1.424(3) ?
Cl1 O1 . 1.441(3) ?
Cl2 O82 . 1.36(3) ?
Cl2 O5 . 1.411(3) ?
Cl2 O6 . 1.418(4) ?
Cl2 O81 . 1.419(17) ?
Cl2 O7 . 1.425(3) ?
N1 C1 . 1.325(5) ?
N1 C5 . 1.347(4) ?
N1 H1 . .78(4) ?
N2 C7 . 1.345(4) ?
N2 C6 . 1.352(4) ?
N2 H6 . .90(4) ?
C1 C2 . 1.369(5) ?
C1 H2 . .92(4) ?
C2 C3 . 1.382(5) ?
C2 H3 . .92(4) ?
C3 C4 . 1.378(5) ?
C3 H4 . 1.02(4) ?
C4 C5 . 1.376(5) ?
C4 H5 . 1.06(3) ?
C5 C6 . 1.452(5) ?
C6 C10 . 1.386(5) ?
C7 C8 . 1.365(5) ?
C7 H7 . 1.02(4) ?
C8 C9 . 1.381(5) ?
C8 H8 . 1.03(4) ?
C9 C10 . 1.396(5) ?
C9 H9 . .96(4) ?
C10 H10 . .92(4) ?
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 O1 2_566 .78(4) 2.13(4) 2.862(4) 157(4)
N2 H6 O7 . .90(4) 1.96(4) 2.817(4) 158(4)
C4 H5 O7 . 1.06(3) 2.45(3) 3.412(5) 151(2)
C7 H7 O6 . 1.02(4) 2.42(4) 3.225(6) 135(3)
C10 H10 O4 1_556 .92(4) 2.41(4) 3.313(5) 168(3)
