data_2202433
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  m787
_journal_page_last  m789
_publ_section_title
;
(1,2-Bis{[3-(2-pyridyl)pyrazol-1-yl]methyl}benzene)perchloratosodium
;
loop_
_publ_author_name
  'Zoe R. Bell'
  'Michael D. Ward'
_chemical_formula_moiety  'C24 H20 Cl N6 Na O4'
_chemical_formula_sum  'C24 H20 Cl N6 Na O4'
_chemical_formula_iupac  '[Na (Cl O4) (C24 H20 N6)]'
_chemical_formula_weight  514.90
_symmetry_cell_setting  Triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  9.353(4)
_cell_length_b  10.558(3)
_cell_length_c  12.794(4)
_cell_angle_alpha  100.26(3)
_cell_angle_beta  107.64(3)
_cell_angle_gamma  97.33(3)
_cell_volume  1162.3(8)
_cell_formula_units_Z  2
_cell_measurement_temperature  173(2)
_exptl_crystal_density_diffrn  1.471
_diffrn_ambient_temperature  173(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
  Na1 0.32557(8) 0.56586(7) 0.25921(6) 0.02888(19) Uani d . 1 . . Na
  N11 0.56446(18) 0.57971(15) 0.41378(13) 0.0297(4) Uani d . 1 . . N
  N21 0.44361(17) 0.37220(14) 0.22393(12) 0.0250(3) Uani d . 1 . . N
  N25 0.42073(18) 0.26114(14) 0.14498(12) 0.0263(4) Uani d . 1 . . N
  N41 0.04076(17) 0.50705(14) 0.17403(12) 0.0246(3) Uani d . 1 . . N
  N45 -0.06916(18) 0.42002(15) 0.08818(12) 0.0265(4) Uani d . 1 . . N
  N51 0.19760(18) 0.73085(15) 0.34344(13) 0.0289(4) Uani d . 1 . . N
  C12 0.6455(2) 0.48469(18) 0.40149(15) 0.0251(4) Uani d . 1 . . C
  C13 0.7866(2) 0.48643(19) 0.48090(16) 0.0304(4) Uani d . 1 . . C
  H13A 0.8405 0.4199 0.4700 0.036 Uiso calc R 1 . . H
  C14 0.8453(2) 0.5879(2) 0.57576(16) 0.0340(5) Uani d . 1 . . C
  H14A 0.9393 0.5909 0.6294 0.041 Uiso calc R 1 . . H
  C15 0.7628(2) 0.6844(2) 0.58981(17) 0.0366(5) Uani d . 1 . . C
  H15A 0.7992 0.7536 0.6532 0.044 Uiso calc R 1 . . H
  C16 0.6244(2) 0.6760(2) 0.50730(17) 0.0371(5) Uani d . 1 . . C
  H16A 0.5690 0.7416 0.5173 0.045 Uiso calc R 1 . . H
  C22 0.5797(2) 0.37638(17) 0.30077(15) 0.0242(4) Uani d . 1 . . C
  C23 0.6413(2) 0.26702(19) 0.27037(16) 0.0302(4) Uani d . 1 . . C
  H23A 0.7340 0.2474 0.3096 0.036 Uiso calc R 1 . . H
  C24 0.5367(2) 0.19541(19) 0.17109(16) 0.0296(4) Uani d . 1 . . C
  H24A 0.5438 0.1163 0.1293 0.036 Uiso calc R 1 . . H
  C26 0.2745(2) 0.21545(19) 0.05395(15) 0.0285(4) Uani d . 1 . . C
  H26A 0.2851 0.1479 -0.0040 0.034 Uiso calc R 1 . . H
  H26B 0.2451 0.2878 0.0205 0.034 Uiso calc R 1 . . H
  C31 0.1507(2) 0.16067(17) 0.09671(14) 0.0242(4) Uani d . 1 . . C
  C32 0.1761(2) 0.05817(18) 0.15151(16) 0.0311(4) Uani d . 1 . . C
  H32A 0.2655 0.0255 0.1584 0.037 Uiso calc R 1 . . H
  C33 0.0714(2) 0.00425(18) 0.19565(16) 0.0339(5) Uani d . 1 . . C
  H33A 0.0905 -0.0637 0.2320 0.041 Uiso calc R 1 . . H
  C34 -0.0622(2) 0.05199(19) 0.18539(16) 0.0341(5) Uani d . 1 . . C
  H34A -0.1326 0.0172 0.2158 0.041 Uiso calc R 1 . . H
  C35 -0.0902(2) 0.15163(19) 0.12970(15) 0.0306(4) Uani d . 1 . . C
  H35A -0.1808 0.1825 0.1219 0.037 Uiso calc R 1 . . H
  C36 0.0149(2) 0.20715(17) 0.08469(14) 0.0238(4) Uani d . 1 . . C
  C42 -0.0358(2) 0.58522(17) 0.22193(15) 0.0248(4) Uani d . 1 . . C
  C43 -0.1939(2) 0.54747(18) 0.16638(16) 0.0301(4) Uani d . 1 . . C
  H43A -0.2707 0.5859 0.1833 0.036 Uiso calc R 1 . . H
  C44 -0.2105(2) 0.44140(19) 0.08155(17) 0.0318(4) Uani d . 1 . . C
  H44A -0.3023 0.3930 0.0291 0.038 Uiso calc R 1 . . H
  C46 -0.0292(2) 0.31220(18) 0.02081(15) 0.0286(4) Uani d . 1 . . C
  H46A 0.0556 0.3465 -0.0015 0.034 Uiso calc R 1 . . H
  H46B -0.1156 0.2732 -0.0472 0.034 Uiso calc R 1 . . H
  C52 0.0464(2) 0.69352(17) 0.32094(15) 0.0260(4) Uani d . 1 . . C
  C53 -0.0303(2) 0.75124(19) 0.38820(16) 0.0315(4) Uani d . 1 . . C
  H53A -0.1348 0.7230 0.3707 0.038 Uiso calc R 1 . . H
  C54 0.0503(3) 0.85098(19) 0.48129(17) 0.0374(5) Uani d . 1 . . C
  H54A 0.0013 0.8894 0.5284 0.045 Uiso calc R 1 . . H
  C55 0.2044(3) 0.89283(19) 0.50341(17) 0.0372(5) Uani d . 1 . . C
  H55A 0.2613 0.9610 0.5647 0.045 Uiso calc R 1 . . H
  C56 0.2718(2) 0.83059(19) 0.43202(17) 0.0351(5) Uani d . 1 . . C
  H56A 0.3755 0.8599 0.4465 0.042 Uiso calc R 1 . . H
  Cl1 0.51614(5) 0.82266(4) 0.19139(4) 0.02962(13) Uani d . 1 . . Cl
  O11 0.45964(19) 0.68368(14) 0.16868(13) 0.0531(4) Uani d . 1 . . O
  O12 0.4673(2) 0.89235(19) 0.27574(14) 0.0677(5) Uani d . 1 . . O
  O13 0.67729(19) 0.84483(18) 0.22873(18) 0.0717(6) Uani d . 1 . . O
  O14 0.4618(2) 0.86635(15) 0.08985(13) 0.0619(5) Uani d . 1 . . 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
  Na1 0.0243(4) 0.0285(4) 0.0317(4) 0.0060(3) 0.0074(3) 0.0045(3)
  N11 0.0280(9) 0.0287(9) 0.0296(9) 0.0062(7) 0.0075(7) 0.0023(7)
  N21 0.0237(9) 0.0245(8) 0.0252(8) 0.0035(6) 0.0075(7) 0.0037(6)
  N25 0.0238(9) 0.0250(8) 0.0278(8) 0.0035(7) 0.0085(7) 0.0013(7)
  N41 0.0254(9) 0.0231(8) 0.0237(8) 0.0039(7) 0.0053(7) 0.0067(6)
  N45 0.0258(9) 0.0250(8) 0.0261(8) 0.0060(7) 0.0046(7) 0.0057(7)
  N51 0.0299(10) 0.0242(8) 0.0306(9) 0.0051(7) 0.0078(7) 0.0054(7)
  C12 0.0249(10) 0.0272(10) 0.0257(9) 0.0028(8) 0.0104(8) 0.0103(8)
  C13 0.0275(11) 0.0328(11) 0.0312(10) 0.0065(9) 0.0072(9) 0.0123(9)
  C14 0.0294(12) 0.0403(12) 0.0278(10) 0.0000(9) 0.0035(9) 0.0124(9)
  C15 0.0382(13) 0.0370(12) 0.0273(10) -0.0018(10) 0.0087(9) -0.0007(9)
  C16 0.0362(13) 0.0359(12) 0.0353(11) 0.0090(9) 0.0094(10) 0.0011(9)
  C22 0.0227(10) 0.0250(10) 0.0257(9) 0.0027(8) 0.0088(8) 0.0079(8)
  C23 0.0255(11) 0.0312(11) 0.0344(10) 0.0089(8) 0.0081(9) 0.0092(9)
  C24 0.0293(11) 0.0259(10) 0.0363(11) 0.0084(8) 0.0152(9) 0.0042(8)
  C26 0.0245(11) 0.0320(11) 0.0246(9) 0.0037(8) 0.0054(8) 0.0014(8)
  C31 0.0238(10) 0.0221(9) 0.0216(9) 0.0003(8) 0.0052(8) -0.0009(7)
  C32 0.0338(12) 0.0240(10) 0.0322(10) 0.0077(8) 0.0073(9) 0.0028(8)
  C33 0.0452(13) 0.0218(10) 0.0319(11) 0.0031(9) 0.0096(10) 0.0068(8)
  C34 0.0377(13) 0.0312(11) 0.0292(10) -0.0069(9) 0.0130(9) 0.0032(9)
  C35 0.0267(11) 0.0315(11) 0.0299(10) 0.0029(8) 0.0081(9) 0.0019(8)
  C36 0.0246(10) 0.0216(9) 0.0189(8) 0.0003(8) 0.0036(8) -0.0014(7)
  C42 0.0274(11) 0.0232(9) 0.0275(9) 0.0078(8) 0.0102(8) 0.0113(8)
  C43 0.0249(11) 0.0298(10) 0.0363(11) 0.0078(8) 0.0097(9) 0.0086(9)
  C44 0.0221(11) 0.0314(11) 0.0398(11) 0.0053(8) 0.0052(9) 0.0113(9)
  C46 0.0289(11) 0.0283(10) 0.0263(10) 0.0071(8) 0.0063(8) 0.0042(8)
  C52 0.0309(11) 0.0225(9) 0.0279(9) 0.0087(8) 0.0094(8) 0.0123(8)
  C53 0.0333(12) 0.0306(11) 0.0355(11) 0.0107(9) 0.0144(9) 0.0118(9)
  C54 0.0543(15) 0.0305(11) 0.0334(11) 0.0161(10) 0.0197(10) 0.0078(9)
  C55 0.0485(15) 0.0265(11) 0.0306(11) 0.0084(10) 0.0065(10) 0.0024(9)
  C56 0.0337(12) 0.0294(11) 0.0373(11) 0.0066(9) 0.0051(9) 0.0074(9)
  Cl1 0.0275(3) 0.0292(3) 0.0320(3) 0.00300(19) 0.0099(2) 0.0085(2)
  O11 0.0639(12) 0.0339(8) 0.0501(10) -0.0124(8) 0.0111(9) 0.0110(7)
  O12 0.0839(15) 0.0761(13) 0.0536(11) 0.0215(11) 0.0410(10) 0.0057(10)
  O13 0.0272(10) 0.0655(12) 0.1143(16) -0.0008(8) 0.0170(10) 0.0190(11)
  O14 0.1025(15) 0.0451(10) 0.0384(9) 0.0258(10) 0.0146(9) 0.0178(8)
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
  Na1 O11 . 2.3359(18) yes
  Na1 N11 . 2.462(2) yes
  Na1 N21 . 2.4805(18) yes
  Na1 N41 . 2.499(2) yes
  Na1 N51 . 2.5046(19) yes
  N11 C16 . 1.339(3) no
  N11 C12 . 1.348(2) no
  N21 C22 . 1.341(2) no
  N21 N25 . 1.351(2) no
  N25 C24 . 1.351(2) no
  N25 C26 . 1.458(2) no
  N41 C42 . 1.344(2) no
  N41 N45 . 1.350(2) no
  N45 C44 . 1.349(2) no
  N45 C46 . 1.461(2) no
  N51 C56 . 1.337(3) no
  N51 C52 . 1.345(2) no
  C12 C13 . 1.396(3) no
  C12 C22 . 1.470(3) no
  C13 C14 . 1.380(3) no
  C13 H13A . 0.9300 no
  C14 C15 . 1.373(3) no
  C14 H14A . 0.9300 no
  C15 C16 . 1.381(3) no
  C15 H15A . 0.9300 no
  C16 H16A . 0.9300 no
  C22 C23 . 1.401(3) no
  C23 C24 . 1.363(3) no
  C23 H23A . 0.9300 no
  C24 H24A . 0.9300 no
  C26 C31 . 1.517(3) no
  C26 H26A . 0.9700 no
  C26 H26B . 0.9700 no
  C31 C36 . 1.395(3) no
  C31 C32 . 1.398(3) no
  C32 C33 . 1.382(3) no
  C32 H32A . 0.9300 no
  C33 C34 . 1.385(3) no
  C33 H33A . 0.9300 no
  C34 C35 . 1.381(3) no
  C34 H34A . 0.9300 no
  C35 C36 . 1.399(3) no
  C35 H35A . 0.9300 no
  C36 C46 . 1.518(2) no
  C42 C43 . 1.401(3) no
  C42 C52 . 1.474(3) no
  C43 C44 . 1.370(3) no
  C43 H43A . 0.9300 no
  C44 H44A . 0.9300 no
  C46 H46A . 0.9700 no
  C46 H46B . 0.9700 no
  C52 C53 . 1.387(3) no
  C53 C54 . 1.379(3) no
  C53 H53A . 0.9300 no
  C54 C55 . 1.378(3) no
  C54 H54A . 0.9300 no
  C55 C56 . 1.380(3) no
  C55 H55A . 0.9300 no
  C56 H56A . 0.9300 no
  Cl1 O13 . 1.4101(19) no
  Cl1 O12 . 1.4200(17) no
  Cl1 O14 . 1.4255(16) no
  Cl1 O11 . 1.4402(16) no