##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4,4'-(2,6-Dihydroxynaphthalene-1,5-diyldimethylene)dipyridinium
bis(perchlorate)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H20 N2 O2 2+, 2(Cl O4 -)'
_chemical_formula_sum     'C22 H20 Cl2 N2 O10'
_chemical_formula_iupac     'C22 H20 N2 O2 2+, 2Cl O4 -'
_chemical_formula_weight     543.30
_chemical_melting_point     ?
_symmetry_cell_setting     'Monoclinic'
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_hall     '-P 2ybc'
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'
_cell_length_a     4.9587(4)
_cell_length_b     13.0399(11)
_cell_length_c     17.8291(16)
_cell_angle_alpha     90.00
_cell_angle_beta     96.767(2)
_cell_angle_gamma     90.00
_cell_volume     1144.82(17)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3755
_cell_measurement_theta_min     2.78
_cell_measurement_theta_max     25.0
_cell_measurement_temperature     296(2)
_exptl_crystal_description     tabular
_exptl_crystal_colour     Yellow
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.576
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     560
_exptl_absorpt_coefficient_mu     0.347
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.925
_exptl_absorpt_correction_T_max     0.988
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6156
_diffrn_reflns_av_R_equivalents     0.0226
_diffrn_reflns_av_sigmaI/netI     0.0258
_diffrn_reflns_theta_min     2.78
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2011
_reflns_number_gt     1610
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0732
_refine_ls_R_factor_gt     0.0587
_refine_ls_wR_factor_gt     0.1437
_refine_ls_wR_factor_ref     0.1512
_refine_ls_goodness_of_fit_ref     1.065
_refine_ls_restrained_S_all     1.065
_refine_ls_number_reflns     2011
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0742P)²+0.8634P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.460
_refine_diff_density_min     -0.270
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_Rogers     .
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'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT (Bruker, 2000)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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
    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_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.072(2) 0.0445(19) 0.065(2) 0.0003(17) -0.007(2) -0.0014(17)
    C2 0.066(2) 0.0429(18) 0.0483(19) 0.0033(15) -0.0006(17) 0.0020(15)
    C3 0.0432(16) 0.0336(15) 0.0431(17) 0.0128(12) -0.0042(13) 0.0051(13)
    C4 0.063(2) 0.0491(19) 0.0459(19) 0.0051(16) -0.0017(16) -0.0011(15)
    C5 0.075(3) 0.058(2) 0.058(2) 0.0047(19) 0.015(2) 0.0109(18)
    C6 0.0447(17) 0.0406(16) 0.0491(19) 0.0056(13) -0.0049(14) 0.0010(14)
    C7 0.0426(16) 0.0362(15) 0.0432(17) 0.0003(13) -0.0020(13) 0.0031(13)
    C8 0.0473(18) 0.0421(17) 0.057(2) 0.0121(14) 0.0068(15) 0.0009(15)
    C9 0.0389(15) 0.0347(15) 0.0428(17) 0.0008(12) 0.0025(13) 0.0038(12)
    C10 0.0540(18) 0.0444(17) 0.0403(17) 0.0031(14) 0.0057(15) 0.0070(14)
    C11 0.061(2) 0.0542(19) 0.0453(19) 0.0124(16) 0.0133(16) 0.0009(15)
    Cl1 0.0550(5) 0.0464(5) 0.0695(6) 0.0110(4) 0.0128(4) 0.0129(4)
    N1 0.0591(18) 0.0398(16) 0.086(2) 0.0005(13) 0.0067(17) 0.0113(16)
    O1 0.0863(18) 0.0700(17) 0.0639(16) 0.0429(14) 0.0108(14) 0.0016(13)
    O2 0.0823(18) 0.0523(15) 0.0787(18) 0.0170(13) 0.0176(14) 0.0166(13)
    O3 0.114(2) 0.0672(17) 0.0640(18) -0.0037(16) 0.0037(16) 0.0161(14)
    O4 0.225(5) 0.077(2) 0.064(2) 0.008(3) 0.010(2) -0.0115(17)
    O5 0.059(2) 0.121(3) 0.360(7) 0.031(2) 0.062(3) 0.132(4)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    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_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
    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_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_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    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) ?
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
data_global
_journal_date_recd_electronic     2008-05-15
_journal_date_accepted     2008-05-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      6
_journal_page_first     o1173
_journal_page_last     o1173
_journal_paper_category     QO
_journal_coeditor_code     WN2262
_publ_contact_author_name     'Zheng Xing'
_publ_contact_author_address
;
School of Material Science and Engineering, Jiangsu University of Science
 and Technology, Zhenjiang, Jiangsu 212003, P. R. China
;
_publ_contact_author_email     xingzheng0410@yahoo.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
4,4'-(2,6-Dihydroxynaphthalene-1,5-diyldimethylene)dipyridinium
bis(perchlorate)
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Zhu, Wei-Feng' .
;
School of Material Science and Engineering
Jiangsu University of Science and Technology
Zhenjiang
Jiangsu 212003
People's Republic of China
;
    'Xing, Zheng' .
;
School of Material Science and Engineering
Jiangsu University of Science and Technology
Zhenjiang
Jiangsu 212003
People's Republic of China
;
