#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011135.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2011135
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  838
_journal_page_last  839
_publ_section_title
;
2-(1,3-Benzimidazol-2-io)-6-(1,3-benzimidazol-2-yl)pyridine perchlorate
monohydrate
;
loop_
_publ_author_name
  'Bo\<ca, Miroslav'
  'Valigura, Du\<san'
  'Svoboda, Ingrid'
  ' Fuess, Hartmut'
  ' Linert, Wolfgang'
_chemical_formula_moiety  'C19 H14 N5 , Cl O4 , H2 O'
_chemical_formula_sum  'C19 H16 Cl N5 O5'
_chemical_formula_iupac  'C19 H14 N5 , Cl O4 , H2 O'
_chemical_formula_weight  429.82
_chemical_melting_point  '>533 K'
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  9.168(2)
_cell_length_b  15.111(3)
_cell_length_c  13.962(3)
_cell_angle_alpha  90.00
_cell_angle_beta  101.98(2)
_cell_angle_gamma  90.00
_cell_volume  1892.1(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  304(2)
_exptl_crystal_density_diffrn  1.509
_diffrn_ambient_temperature  304(2)
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  .16383(6)  .77420(4)  .93722(4)  .04998(18) Uani d D 1 . . Cl
  N1  .20055(17)  .57133(11)  .50065(11)  .0387(4) Uani d . 1 . . N
  N2  .13392(19)  .47630(11)  .65879(12)  .0419(4) Uani d . 1 . . N
  H4  .185(3)  .4471(18)  .6280(19)  .066(8) Uiso d . 1 . . H
  N5  .36428(18)  .60336(11)  .28842(12)  .0416(4) Uani d . 1 . . N
  H14  .351(3)  .6618(18)  .2653(17)  .061(7) Uiso d . 1 . . H
  N4  .36143(18)  .48703(11)  .37923(12)  .0423(4) Uani d . 1 . . N
  H9  .335(3)  .4511(17)  .4261(18)  .061(7) Uiso d . 1 . . H
  C13  .3175(2)  .57084(12)  .36520(13)  .0384(4) Uani d . 1 . . C
  C6  .0892(2)  .56049(13)  .64022(13)  .0391(4) Uani d . 1 . . C
  N3  .00878(18)  .59072(11)  .70164(12)  .0426(4) Uani d . 1 . . N
  C5  .1293(2)  .61341(13)  .56145(14)  .0398(4) Uani d . 1 . . C
  C1  .2349(2)  .61944(13)  .42772(13)  .0383(4) Uani d . 1 . . C
  C12  .0021(2)  .52080(13)  .76458(13)  .0406(4) Uani d . 1 . . C
  C19  .4409(2)  .53770(13)  .25045(14)  .0423(4) Uani d . 1 . . C
  C2  .2000(2)  .70780(14)  .41210(16)  .0477(5) Uani d . 1 . . C
  H1  .2233  .7380  .3592  .057 Uiso calc R 1 . . H
  C7  .0806(2)  .44821(13)  .73895(14)  .0415(4) Uani d . 1 . . C
  C14  .4388(2)  .46332(13)  .30806(14)  .0424(4) Uani d . 1 . . C
  C11  -.0677(2)  .51506(15)  .84440(15)  .0492(5) Uani d . 1 . . C
  H8  -.1203  .5627  .8624  .059 Uiso calc R 1 . . H
  C18  .5098(3)  .53745(16)  .17092(16)  .0545(5) Uani d . 1 . . C
  H13  .5094  .5872  .1316  .065 Uiso calc R 1 . . H
  C17  .5782(3)  .46066(17)  .15312(18)  .0614(6) Uani d . 1 . . C
  H12  .6263  .4582  .1007  .074 Uiso calc R 1 . . H
  C10  -.0560(3)  .43728(16)  .89485(15)  .0557(6) Uani d . 1 . . C
  H7  -.1034  .4316  .9473  .067 Uiso calc R 1 . . H
  C16  .5777(3)  .38597(16)  .21158(18)  .0607(6) Uani d . 1 . . C
  H11  .6260  .3351  .1972  .073 Uiso calc R 1 . . H
  C15  .5083(2)  .38510(15)  .28975(17)  .0533(5) Uani d . 1 . . C
  H10  .5078  .3350  .3283  .064 Uiso calc R 1 . . H
  C3  .1295(3)  .74988(15)  .47726(18)  .0551(6) Uani d . 1 . . C
  H2  .1060  .8097  .4699  .066 Uiso calc R 1 . . H
  C4  .0943(2)  .70257(14)  .55304(16)  .0509(5) Uani d . 1 . . C
  H3  .0475  .7300  .5982  .061 Uiso calc R 1 . . H
  C8  .0950(3)  .36991(14)  .79155(16)  .0534(5) Uani d . 1 . . C
  H5  .1491  .3223  .7749  .064 Uiso calc R 1 . . H
  C9  .0251(3)  .36604(15)  .86967(16)  .0577(6) Uani d . 1 . . C
  H6  .0323  .3145  .9067  .069 Uiso calc R 1 . . H
  O1  .1782(2)  .26268(12)  .29595(14)  .0567(4) Uani d . 1 . . O
  H15  .216(3)  .2594(19)  .352(2)  .067(9) Uiso d . 1 . . H
  H16  .121(4)  .305(2)  .289(2)  .085(10) Uiso d . 1 . . H
  O2  .2635(2)  .71005(14)  .98700(16)  .0825(6) Uani d D 1 A . O
  O3  .1728(8)  .7800(4)  .8351(4)  .0757(15) Uani d PD  .553(9) A 1 O
  O7  .0188(6)  .7619(6)  .9455(7)  .120(4) Uani d PD  .553(9) A 1 O
  O5  .2153(8)  .8640(3)  .9740(3)  .109(2) Uani d PD  .553(9) A 1 O
  O8  .0288(8)  .7249(4)  .9028(5)  .0725(18) Uani d PD  .447(9) A 2 O
  O6  .1348(7)  .8294(4) 1.0109(4)  .096(3) Uani d PD  .447(9) A 2 O
  O4  .2131(10)  .8116(6)  .8650(7)  .092(2) Uani d PD  .447(9) A 2 O
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
  Cl1  .0475(3)  .0548(3)  .0512(3)  .0017(2)  .0183(2)  -.0021(2)
  N1  .0373(8)  .0401(8)  .0416(8)  -.0012(6)  .0147(7)  .0024(7)
  N2  .0471(9)  .0398(9)  .0447(9)  .0016(7)  .0232(7)  .0001(7)
  N5  .0479(9)  .0372(9)  .0438(9)  -.0042(7)  .0193(7)  .0008(7)
  N4  .0448(9)  .0391(9)  .0467(9)  -.0014(7)  .0179(7)  .0047(7)
  C13  .0373(10)  .0389(10)  .0413(9)  -.0051(8)  .0132(8)  .0020(8)
  C6  .0393(10)  .0395(10)  .0414(10)  -.0006(7)  .0151(8)  .0007(8)
  N3  .0445(9)  .0414(9)  .0469(9)  .0010(7)  .0214(7)  .0010(7)
  C5  .0347(9)  .0433(10)  .0439(10)  -.0001(7)  .0137(8)  .0030(8)
  C1  .0341(9)  .0412(10)  .0416(10)  -.0017(7)  .0125(8)  .0025(8)
  C12  .0416(10)  .0428(10)  .0396(9)  -.0055(8)  .0136(8)  -.0023(8)
  C19  .0426(10)  .0414(10)  .0459(10)  -.0075(8)  .0160(8)  -.0046(8)
  C2  .0473(11)  .0468(11)  .0541(11)  .0048(9)  .0226(9)  .0126(9)
  C7  .0436(10)  .0430(10)  .0407(10)  -.0062(8)  .0155(8)  -.0011(8)
  C14  .0389(10)  .0427(10)  .0477(10)  -.0059(8)  .0137(8)  -.0039(8)
  C11  .0518(12)  .0545(12)  .0470(11)  -.0063(9)  .0237(9)  -.0079(9)
  C18  .0619(13)  .0558(13)  .0533(12)  -.0101(10)  .0291(10)  -.0049(10)
  C17  .0623(14)  .0688(16)  .0617(14)  -.0084(11)  .0325(11)  -.0189(12)
  C10  .0667(14)  .0619(14)  .0449(11)  -.0192(11)  .0261(10)  -.0039(10)
  C16  .0540(13)  .0569(14)  .0745(15)  .0021(10)  .0211(11)  -.0209(12)
  C15  .0537(13)  .0437(12)  .0642(13)  .0007(9)  .0165(11)  -.0035(10)
  C3  .0586(13)  .0423(11)  .0717(14)  .0130(10)  .0301(11)  .0131(10)
  C4  .0510(12)  .0479(11)  .0615(12)  .0099(9)  .0297(10)  .0068(10)
  C8  .0681(14)  .0414(11)  .0562(12)  -.0010(10)  .0252(11)  .0035(9)
  C9  .0754(16)  .0480(12)  .0540(12)  -.0125(11)  .0237(11)  .0059(10)
  O1  .0615(10)  .0526(10)  .0566(11)  .0142(8)  .0139(8)  -.0129(8)
  O2  .0607(11)  .0836(14)  .0992(14)  .0086(9)  .0074(10)  .0200(11)
  O3  .092(4)  .081(4)  .058(2)  .001(3)  .027(2)  -.001(2)
  O7  .048(2)  .176(8)  .150(7)  .031(4)  .054(4)  .100(6)
  O5  .186(6)  .064(3)  .093(3)  -.014(3)  .070(3)  -.025(2)
  O8  .050(3)  .079(3)  .084(4)  -.021(2)  .003(2)  -.001(3)
  O6  .136(5)  .072(3)  .092(4)  -.019(3)  .052(3)  -.039(3)
  O4  .125(6)  .083(5)  .084(5)  -.033(4)  .057(4)  .018(4)
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 O4 . 1.316(6) ?
  Cl1 O7 . 1.371(5) ?
  Cl1 O6 . 1.392(4) ?
  Cl1 O2 . 1.412(2) ?
  Cl1 O8 . 1.439(6) ?
  Cl1 O3 . 1.448(5) ?
  Cl1 O5 . 1.492(5) ?
  N1 C5 . 1.335(2) yes
  N1 C1 . 1.341(2) yes
  N2 C6 . 1.345(3) yes
  N2 C7 . 1.378(2) yes
  N2 H4 .  .83(3) ?
  N5 C13 . 1.329(2) yes
  N5 C19 . 1.383(3) yes
  N5 H14 .  .94(3) ?
  N4 C13 . 1.331(3) yes
  N4 C14 . 1.382(2) yes
  N4 H9 .  .92(3) ?
  C13 C1 . 1.466(3) yes
  C6 N3 . 1.323(2) yes
  C6 C5 . 1.467(3) yes
  N3 C12 . 1.384(2) yes
  C5 C4 . 1.384(3) ?
  C1 C2 . 1.380(3) ?
  C12 C11 . 1.398(3) ?
  C12 C7 . 1.399(3) ?
  C19 C14 . 1.385(3) ?
  C19 C18 . 1.387(3) ?
  C2 C3 . 1.376(3) ?
  C2 H1 .  .9300 ?
  C7 C8 . 1.384(3) ?
  C14 C15 . 1.392(3) ?
  C11 C10 . 1.363(3) ?
  C11 H8 .  .9300 ?
  C18 C17 . 1.366(3) ?
  C18 H13 .  .9300 ?
  C17 C16 . 1.393(4) ?
  C17 H12 .  .9300 ?
  C10 C9 . 1.394(3) ?
  C10 H7 .  .9300 ?
  C16 C15 . 1.373(3) ?
  C16 H11 .  .9300 ?
  C15 H10 .  .9300 ?
  C3 C4 . 1.370(3) ?
  C3 H2 .  .9300 ?
  C4 H3 .  .9300 ?
  C8 C9 . 1.376(3) ?
  C8 H5 .  .9300 ?
  C9 H6 .  .9300 ?
  O1 H15 .  .79(3) ?
  O1 H16 .  .82(4) ?