##############################################################################
###                                                                        ###
###        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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# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
4-(4-Pyridyl)pyridinium perchlorate methanol solvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H9 N2 + , Cl O4 -, C H4 O'
_chemical_formula_sum     'C11 H13 Cl N2 O5'
_chemical_formula_iupac     'C10 H9 N2 + , Cl O4 -, C H4 O'
_chemical_formula_weight     288.68
_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     6.8822(14)
_cell_length_b     15.362(3)
_cell_length_c     12.254(3)
_cell_angle_alpha     90.00
_cell_angle_beta     92.07(3)
_cell_angle_gamma     90.00
_cell_volume     1294.7(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1803
_cell_measurement_theta_min     3.13
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.2
_exptl_crystal_density_diffrn     1.481
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     600
_exptl_absorpt_coefficient_mu     0.313
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrystalClear; Rigaku, 2005)'
_exptl_absorpt_correction_T_min     0.62
_exptl_absorpt_correction_T_max     0.81
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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     'Rigaku SCXmini'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     13.6612
_diffrn_reflns_number     13295
_diffrn_reflns_av_R_equivalents     0.0673
_diffrn_reflns_av_sigmaI/netI     0.0551
_diffrn_reflns_theta_min     3.13
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_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     2956
_reflns_number_gt     1803
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1251
_refine_ls_R_factor_gt     0.0786
_refine_ls_wR_factor_gt     0.1848
_refine_ls_wR_factor_ref     0.2100
_refine_ls_goodness_of_fit_ref     1.000
_refine_ls_restrained_S_all     1.088
_refine_ls_number_reflns     2956
_refine_ls_number_parameters     201
_refine_ls_number_restraints     88
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0767P)²+2.5927P] 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     0.630
_refine_diff_density_min     -0.597
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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     'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement     'CrystalClear (Rigaku, 2005)'
_computing_data_reduction     'CrystalClear (Rigaku, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXL97 (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 0.7627(6) 0.5390(3) 0.5916(4) 0.0459(11) Uani d . 1 . .
    H H1A 0.7704 0.5882 0.6356 0.055 Uiso calc R 1 . .
    C C2 0.7575(6) 0.5504(3) 0.4801(3) 0.0395(10) Uani d . 1 . .
    H H2A 0.7624 0.6061 0.4505 0.047 Uiso calc R 1 . .
    C C3 0.7449(6) 0.4786(3) 0.4128(3) 0.0348(9) Uani d . 1 . .
    C C4 0.7326(7) 0.3979(3) 0.4625(4) 0.0464(11) Uani d . 1 . .
    H H4A 0.7185 0.3478 0.4205 0.056 Uiso calc R 1 . .
    C C5 0.7414(7) 0.3929(3) 0.5742(4) 0.0522(12) Uani d . 1 . .
    H H5A 0.7360 0.3380 0.6060 0.063 Uiso calc R 1 . .
    C C6 0.6765(7) 0.5634(4) 0.1258(4) 0.0564(13) Uani d . 1 . .
    H H6A 0.6278 0.6121 0.0889 0.068 Uiso calc R 1 . .
    C C7 0.6747(7) 0.5599(3) 0.2371(4) 0.0469(11) Uani d . 1 . .
    H H7A 0.6270 0.6067 0.2763 0.056 Uiso calc R 1 . .
    C C8 0.7450(6) 0.4859(3) 0.2922(3) 0.0370(9) Uani d . 1 . .
    C C9 0.8198(7) 0.4193(3) 0.2298(4) 0.0494(11) Uani d . 1 . .
    H H9A 0.8702 0.3696 0.2637 0.059 Uiso calc R 1 . .
    C C10 0.8194(8) 0.4267(4) 0.1186(4) 0.0565(13) Uani d . 1 . .
    H H10A 0.8698 0.3820 0.0769 0.068 Uiso calc R 1 . .
    C C11 0.1539(10) 0.6691(3) 0.1471(5) 0.0727(17) Uani d . 1 . .
    H H11A 0.0837 0.6922 0.0844 0.087 Uiso calc R 1 . .
    H H11B 0.2789 0.6967 0.1541 0.087 Uiso calc R 1 . .
    H H11C 0.0823 0.6801 0.2114 0.087 Uiso calc R 1 . .
    N N1 0.7476(6) 0.4972(3) 0.0702(3) 0.0547(11) Uani d . 1 . .
    H H1B 0.7470 0.5003 0.0002 0.066 Uiso calc R 1 . .
    N N2 0.7572(5) 0.4616(3) 0.6398(3) 0.0472(9) Uani d . 1 . .
    O O5 0.1785(5) 0.5786(2) 0.1341(2) 0.0537(9) Uani d . 1 . .
    H H5 0.2107 0.5599 0.2002 0.081 Uiso d R 1 . .
    Cl Cl1 0.32539(19) 0.19524(7) 0.64038(10) 0.0531(4) Uani d U 1 . .
    O O1 0.3132(6) 0.1030(2) 0.6349(3) 0.0634(9) Uani d U 1 A .
    O O2 0.335(2) 0.2182(8) 0.7540(9) 0.0659(15) Uani d PU 0.351(7) A 1
    O O3 0.1581(17) 0.2295(7) 0.5822(11) 0.0606(9) Uani d PU 0.351(7) A 1
    O O4 0.3801(19) 0.2310(7) 0.5350(9) 0.0601(9) Uani d PU 0.351(7) A 1
    O O2' 0.4433(12) 0.2213(4) 0.7329(6) 0.0739(13) Uani d PU 0.649(7) A 2
    O O3' 0.1388(10) 0.2337(4) 0.6422(7) 0.0717(12) Uani d PU 0.649(7) A 2
    O O4' 0.4702(11) 0.2228(4) 0.5685(6) 0.0732(12) Uani d PU 0.649(7) A 2
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 0.046(3) 0.048(3) 0.044(3) 0.001(2) 0.000(2) -0.008(2)
    C2 0.042(2) 0.036(2) 0.040(2) 0.0015(18) -0.0002(18) 0.0001(17)
    C3 0.032(2) 0.039(2) 0.034(2) 0.0004(17) 0.0020(16) 0.0025(17)
    C4 0.062(3) 0.036(2) 0.041(2) -0.005(2) -0.001(2) -0.0002(18)
    C5 0.065(3) 0.049(3) 0.042(2) -0.004(2) 0.003(2) 0.009(2)
    C6 0.050(3) 0.073(3) 0.046(3) -0.002(3) -0.001(2) 0.018(3)
    C7 0.049(3) 0.050(3) 0.042(2) 0.003(2) 0.004(2) 0.008(2)
    C8 0.034(2) 0.043(2) 0.033(2) -0.0030(18) 0.0007(17) 0.0013(17)
    C9 0.055(3) 0.051(3) 0.042(3) 0.005(2) 0.003(2) -0.005(2)
    C10 0.059(3) 0.073(4) 0.038(3) -0.002(3) 0.002(2) -0.011(2)
    C11 0.110(5) 0.051(3) 0.056(3) 0.008(3) -0.010(3) -0.003(3)
    N1 0.043(2) 0.089(3) 0.0322(19) -0.011(2) -0.0008(17) 0.004(2)
    N2 0.047(2) 0.059(2) 0.0356(19) -0.0010(18) 0.0017(16) 0.0006(18)
    O5 0.082(2) 0.0453(18) 0.0341(16) 0.0012(16) -0.0031(15) 0.0001(13)
    Cl1 0.0674(8) 0.0371(6) 0.0546(7) -0.0098(5) 0.0003(5) -0.0051(5)
    O1 0.093(2) 0.0369(12) 0.0603(19) -0.0094(12) 0.0059(17) -0.0059(12)
    O2 0.084(3) 0.055(3) 0.0592(16) -0.012(3) 0.000(2) -0.015(2)
    O3 0.0715(16) 0.0479(16) 0.0622(17) -0.0064(14) -0.0005(14) -0.0015(16)
    O4 0.0722(17) 0.0470(16) 0.0609(15) -0.0095(16) 0.0001(15) 0.0018(14)
    O2' 0.084(3) 0.063(2) 0.074(2) -0.014(3) -0.010(2) -0.019(2)
    O3' 0.0757(18) 0.062(2) 0.077(3) 0.0039(18) 0.004(2) -0.011(2)
    O4' 0.074(2) 0.066(2) 0.080(2) -0.017(2) 0.007(2) 0.012(2)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell esds are taken into
account individually in the estimation of esds in distances, angles and
torsion angles; correlations between esds in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 N2 . 1.329(6) ?
    C1 C2 . 1.376(6) ?
    C1 H1A . 0.9300 ?
    C2 C3 . 1.379(6) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.384(6) ?
    C3 C8 . 1.481(5) ?
    C4 C5 . 1.370(6) ?
    C4 H4A . 0.9300 ?
    C5 N2 . 1.329(6) ?
    C5 H5A . 0.9300 ?
    C6 N1 . 1.327(7) ?
    C6 C7 . 1.366(7) ?
    C6 H6A . 0.9300 ?
    C7 C8 . 1.400(6) ?
    C7 H7A . 0.9300 ?
    C8 C9 . 1.387(6) ?
    C9 C10 . 1.368(6) ?
    C9 H9A . 0.9300 ?
    C10 N1 . 1.322(7) ?
    C10 H10A . 0.9300 ?
    C11 O5 . 1.411(6) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    N1 H1B . 0.8600 ?
    O5 H5 . 0.8804 ?
    Cl1 O3' . 1.415(7) ?
    Cl1 O4' . 1.419(6) ?
    Cl1 O1 . 1.420(3) ?
    Cl1 O2' . 1.428(6) ?
    Cl1 O3 . 1.432(12) ?
    Cl1 O2 . 1.435(11) ?
    Cl1 O4 . 1.465(11) ?
    O3 O4 . 1.653(19) ?
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
    N2 C1 C2 . . 123.8(4) ?
    N2 C1 H1A . . 118.1 ?
    C2 C1 H1A . . 118.1 ?
    C1 C2 C3 . . 119.3(4) ?
    C1 C2 H2A . . 120.3 ?
    C3 C2 H2A . . 120.3 ?
    C2 C3 C4 . . 117.2(4) ?
    C2 C3 C8 . . 122.3(4) ?
    C4 C3 C8 . . 120.6(4) ?
    C5 C4 C3 . . 119.3(4) ?
    C5 C4 H4A . . 120.4 ?
    C3 C4 H4A . . 120.4 ?
    N2 C5 C4 . . 124.0(4) ?
    N2 C5 H5A . . 118.0 ?
    C4 C5 H5A . . 118.0 ?
    N1 C6 C7 . . 120.0(5) ?
    N1 C6 H6A . . 120.0 ?
    C7 C6 H6A . . 120.0 ?
    C6 C7 C8 . . 119.9(5) ?
    C6 C7 H7A . . 120.1 ?
    C8 C7 H7A . . 120.1 ?
    C9 C8 C7 . . 117.5(4) ?
    C9 C8 C3 . . 120.5(4) ?
    C7 C8 C3 . . 122.0(4) ?
    C10 C9 C8 . . 120.0(5) ?
    C10 C9 H9A . . 120.0 ?
    C8 C9 H9A . . 120.0 ?
    N1 C10 C9 . . 120.1(5) ?
    N1 C10 H10A . . 119.9 ?
    C9 C10 H10A . . 119.9 ?
    O5 C11 H11A . . 109.5 ?
    O5 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    O5 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C10 N1 C6 . . 122.5(4) ?
    C10 N1 H1B . . 118.8 ?
    C6 N1 H1B . . 118.8 ?
    C1 N2 C5 . . 116.4(4) ?
    C11 O5 H5 . . 104.2 ?
    O3' Cl1 O4' . . 122.9(5) ?
    O3' Cl1 O1 . . 111.4(3) ?
    O4' Cl1 O1 . . 108.1(3) ?
    O3' Cl1 O2' . . 111.1(4) ?
    O4' Cl1 O2' . . 91.0(6) ?
    O1 Cl1 O2' . . 110.4(3) ?
    O4' Cl1 O3 . . 98.7(7) ?
    O1 Cl1 O3 . . 107.3(5) ?
    O2' Cl1 O3 . . 135.7(6) ?
    O3' Cl1 O2 . . 83.7(6) ?
    O4' Cl1 O2 . . 121.4(7) ?
    O1 Cl1 O2 . . 106.9(5) ?
    O3 Cl1 O2 . . 113.5(7) ?
    O3' Cl1 O4 . . 96.9(7) ?
    O1 Cl1 O4 . . 110.4(5) ?
    O2' Cl1 O4 . . 116.0(7) ?
    O3 Cl1 O4 . . 69.6(8) ?
    O2 Cl1 O4 . . 139.4(7) ?
    Cl1 O3 O4 . . 56.1(6) ?
    Cl1 O4 O3 . . 54.3(6) ?
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
    O5 H5 N2 3_666 0.88 1.99 2.857(5) 167.1
    N1 H1B O5 3_665 0.86 2.12 2.825(5) 138.6
    N1 H1B O1 2_655 0.86 2.31 3.010(5) 138.3
data_global
_journal_date_recd_electronic     2010-03-25
_journal_date_accepted     2010-04-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      5
_journal_page_first     o1068
_journal_page_last     o1068
_journal_paper_category     QO
_journal_coeditor_code     RZ2430
_publ_contact_author_name     'Yu-Hua Gao'
_publ_contact_author_address
;
School of Materials Science and Engineering
Jiangsu University of Science and Technology
Zhenjiang 212003
People's Republic of China
;
_publ_contact_author_email     gaoyuhua8888@sina.com
_publ_contact_author_fax     '+86-511-84401181'
_publ_contact_author_phone     '+86-511-84401181'
_publ_section_title
;
4-(4-Pyridyl)pyridinium perchlorate methanol solvate
;
loop_
    _publ_author_name
    _publ_author_address
    'Gao, Yu-Hua'
;
School of Materials Science and Engineering
Jiangsu University of Science and Technology
Zhenjiang 212003
People's Republic of China
;
    'Wu, De-Ming'
;
School of Materials Science and Engineering
Jiangsu University of Science and Technology
Zhenjiang 212003
People's Republic of China
;
