#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/85/2218567.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_2218567
loop_
_publ_author_name
'Zhu, Wei-Feng'
'Xing, Zheng'
_publ_section_title
;
 4,4'-(2,6-Dihydroxynaphthalene-1,5-diyldimethylene)dipyridinium
 bis(perchlorate)
;
_journal_coeditor_code           WN2262
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1173
_journal_paper_doi               10.1107/S1600536808015092
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C22 H20 N2 O2 2+, 2Cl O4 -'
_chemical_formula_moiety         'C22 H20 N2 O2 2+, 2(Cl O4 -)'
_chemical_formula_sum            'C22 H20 Cl2 N2 O10'
_chemical_formula_weight         543.30
_chemical_name_systematic
;
4,4'-(2,6-Dihydroxynaphthalene-1,5-diyldimethylene)dipyridinium
bis(perchlorate)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 96.767(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.9587(4)
_cell_length_b                   13.0399(11)
_cell_length_c                   17.8291(16)
_cell_measurement_reflns_used    3755
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.78
_cell_volume                     1144.82(17)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD 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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6156
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0587
_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)+(0.0742P)²+0.8634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1512
_reflns_number_gt                1610
_reflns_number_total             2011
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2262.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2218567
_cod_database_fobs_code          2218567
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C C1 -0.1573(8) 0.1073(3) 0.0739(2) 0.0616(10) Uani d . 1
H H1A -0.2367 0.0654 0.0352 0.074 Uiso calc R 1
C C2 0.0188(7) 0.1821(2) 0.0583(2) 0.0529(8) Uani d . 1
H H2A 0.0589 0.1915 0.0092 0.063 Uiso calc R 1
C C3 0.1388(6) 0.2445(2) 0.11614(17) 0.0407(7) Uani d . 1
C C4 0.0721(7) 0.2263(3) 0.18810(19) 0.0532(8) Uani d . 1
H H4A 0.1488 0.2662 0.2283 0.064 Uiso calc R 1
C C5 -0.1058(8) 0.1501(3) 0.2003(2) 0.0630(10) Uani d . 1
H H5A -0.1492 0.1378 0.2488 0.076 Uiso calc R 1
C C6 0.3317(6) 0.3289(2) 0.10067(18) 0.0456(8) Uani d . 1
H H6A 0.5071 0.2991 0.0947 0.055 Uiso calc R 1
H H6B 0.3558 0.3746 0.1439 0.055 Uiso calc R 1
C C7 0.2348(6) 0.3905(2) 0.03090(17) 0.0412(7) Uani d . 1
C C8 0.3277(6) 0.3667(2) -0.03634(19) 0.0489(8) Uani d . 1
C C9 0.0446(6) 0.4723(2) 0.03359(17) 0.0390(7) Uani d . 1
C C10 -0.0624(6) 0.4991(2) 0.10063(17) 0.0462(8) Uani d . 1
H H10A -0.0082 0.4628 0.1447 0.055 Uiso calc R 1
C C11 -0.2443(7) 0.5773(3) 0.10207(19) 0.0531(8) Uani d . 1
H H11A -0.3133 0.5936 0.1469 0.080 Uiso calc R 1
Cl Cl1 0.28576(17) 0.89190(6) 0.17150(5) 0.0565(3) Uani d . 1
N N1 -0.2164(6) 0.0937(2) 0.1433(2) 0.0618(8) Uani d . 1
H H1B -0.3305 0.0466 0.1518 0.093 Uiso calc R 1
O O1 0.5047(5) 0.2863(2) -0.03716(15) 0.0732(8) Uani d . 1
H H1C 0.5186 0.2701 -0.0810 0.110 Uiso calc R 1
O O2 0.3960(6) 0.79156(19) 0.18131(15) 0.0704(8) Uani d . 1
O O3 0.3505(7) 0.9360(2) 0.10369(15) 0.0823(9) Uani d . 1
O O4 0.4082(10) 0.9556(3) 0.22951(18) 0.1228(15) Uani d . 1
O O5 0.0089(7) 0.8878(3) 0.1717(4) 0.177(3) Uani 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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N1 C1 C2 . . 120.5(3)
N1 C1 H1A . . 119.7
C2 C1 H1A . . 119.7
C1 C2 C3 . . 119.9(3)
C1 C2 H2A . . 120.1
C3 C2 H2A . . 120.1
C4 C3 C2 . . 117.3(3)
C4 C3 C6 . . 121.5(3)
C2 C3 C6 . . 121.2(3)
C5 C4 C3 . . 120.2(3)
C5 C4 H4A . . 119.9
C3 C4 H4A . . 119.9
N1 C5 C4 . . 120.1(4)
N1 C5 H5A . . 119.9
C4 C5 H5A . . 119.9
C3 C6 C7 . . 113.1(2)
C3 C6 H6A . . 109.0
C7 C6 H6A . . 109.0
C3 C6 H6B . . 109.0
C7 C6 H6B . . 109.0
H6A C6 H6B . . 107.8
C8 C7 C9 . . 119.3(3)
C8 C7 C6 . . 119.6(3)
C9 C7 C6 . . 121.1(3)
O1 C8 C7 . . 117.7(3)
O1 C8 C11 . 3_565 121.1(3)
C7 C8 C11 . 3_565 121.2(3)
C10 C9 C9 . 3_565 118.5(3)
C10 C9 C7 . . 122.0(3)
C9 C9 C7 3_565 . 119.5(3)
C11 C10 C9 . . 121.2(3)
C11 C10 H10A . . 119.4
C9 C10 H10A . . 119.4
C10 C11 C8 . 3_565 120.3(3)
C10 C11 H11A . . 119.8
C8 C11 H11A 3_565 . 119.8
O5 Cl1 O4 . . 111.5(3)
O5 Cl1 O3 . . 110.3(3)
O4 Cl1 O3 . . 105.5(2)
O5 Cl1 O2 . . 109.5(2)
O4 Cl1 O2 . . 109.1(2)
O3 Cl1 O2 . . 110.97(17)
C1 N1 C5 . . 122.0(3)
C1 N1 H1B . . 119.0
C5 N1 H1B . . 119.0
C8 O1 H1C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.318(5)
C1 C2 . 1.359(5)
C1 H1A . 0.9300
C2 C3 . 1.391(4)
C2 H2A . 0.9300
C3 C4 . 1.383(4)
C3 C6 . 1.504(4)
C4 C5 . 1.363(5)
C4 H4A . 0.9300
C5 N1 . 1.320(5)
C5 H5A . 0.9300
C6 C7 . 1.511(4)
C6 H6A . 0.9700
C6 H6B . 0.9700
C7 C8 . 1.370(4)
C7 C9 . 1.429(4)
C8 O1 . 1.369(4)
C8 C11 3_565 1.401(5)
C9 C10 . 1.408(4)
C9 C9 3_565 1.424(6)
C10 C11 . 1.364(4)
C10 H10A . 0.9300
C11 C8 3_565 1.401(5)
C11 H11A . 0.9300
Cl1 O5 . 1.374(3)
Cl1 O4 . 1.407(4)
Cl1 O3 . 1.409(3)
Cl1 O2 . 1.421(3)
N1 H1B . 0.8600
O1 H1C . 0.8200
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
O1 H1C O2 3_665 0.82 2.05 2.859(4) 168.9
N1 H1B O3 1_445 0.86 2.24 2.997(4) 147.5
N1 H1B O4 1_445 0.86 2.33 3.121(5) 153.0
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
N1 C1 C2 C3 . . 0.3(5)
C1 C2 C3 C4 . . 0.4(4)
C1 C2 C3 C6 . . -179.2(3)
C2 C3 C4 C5 . . -0.3(5)
C6 C3 C4 C5 . . 179.2(3)
C3 C4 C5 N1 . . -0.4(5)
C4 C3 C6 C7 . . -135.8(3)
C2 C3 C6 C7 . . 43.7(4)
C3 C6 C7 C8 . . -96.3(3)
C3 C6 C7 C9 . . 82.8(3)
C9 C7 C8 O1 . . -178.5(3)
C6 C7 C8 O1 . . 0.6(5)
C9 C7 C8 C11 . 3_565 1.5(5)
C6 C7 C8 C11 . 3_565 -179.4(3)
C8 C7 C9 C10 . . 178.7(3)
C6 C7 C9 C10 . . -0.4(4)
C8 C7 C9 C9 . 3_565 -0.1(5)
C6 C7 C9 C9 . 3_565 -179.2(3)
C9 C9 C10 C11 3_565 . -1.1(5)
C7 C9 C10 C11 . . -179.9(3)
C9 C10 C11 C8 . 3_565 -0.3(5)
C2 C1 N1 C5 . . -1.1(5)
C4 C5 N1 C1 . . 1.1(5)
