#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008970.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_2008970
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  1489
_journal_page_last  1492
_publ_section_title
;
Linking of C^4^~4~(32)[R^4^~4~(30)] chains of rings in the
hydrogen-bonded adduct  3,5-dihydroxybenzoic acid--4,4'-bipyridine
(2/3) by means of \p...\p stacking interactions.
;
loop_
_publ_author_name
  'Wheatley, Paul S.'
  'Lough, Alan J.'
  'Ferguson, George'
  'Glidewell, Christopher'
_chemical_formula_moiety  '2C7 H6 O4 , 3C10 H8 N2'
_chemical_formula_sum  'C44 H36 N6 O8'
_chemical_formula_weight  776.79
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  9.6826(11)
_cell_length_b  14.378(3)
_cell_length_c  14.797(3)
_cell_angle_alpha  63.17(6)
_cell_angle_beta  83.25(11)
_cell_angle_gamma  80.17(10)
_cell_volume  1809.4(5)
_cell_formula_units_Z  2
_cell_measurement_temperature  100.00(10)
_exptl_crystal_density_diffrn  1.426
_diffrn_ambient_temperature  100.00(10)
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
  O11 -0.57896(19) -0.01365(18) 0.37266(18) 0.0343(6) Uani d . 1 . . O
  O12 -0.58958(19) 0.08040(18) 0.20409(17) 0.0339(6) Uani d . 1 . . O
  O13 -0.17483(19) 0.10640(19) 0.45719(17) 0.0365(6) Uani d . 1 . . O
  O15 -0.16676(19) 0.26735(18) 0.09362(16) 0.0326(6) Uani d . 1 . . O
  C11 -0.4032(3) 0.0984(2) 0.2828(3) 0.0261(8) Uani d . 1 . . C
  C12 -0.3468(3) 0.0802(2) 0.3733(3) 0.0282(8) Uani d . 1 . . C
  C13 -0.2283(3) 0.1251(3) 0.3676(3) 0.0284(8) Uani d . 1 . . C
  C14 -0.1673(3) 0.1877(2) 0.2752(2) 0.0273(8) Uani d . 1 . . C
  C15 -0.2251(3) 0.2051(2) 0.1861(3) 0.0279(8) Uani d . 1 . . C
  C16 -0.3427(3) 0.1608(2) 0.1897(3) 0.0270(8) Uani d . 1 . . C
  C17 -0.5315(3) 0.0486(3) 0.2924(3) 0.0292(8) Uani d . 1 . . C
  O21 1.2925(2) 0.71672(18) 0.31826(18) 0.0364(6) Uani d . 1 . . O
  O22 1.28332(19) 0.80208(18) 0.14932(17) 0.0357(6) Uani d . 1 . . O
  O23 0.8564(2) 0.54113(18) 0.43047(17) 0.0362(6) Uani d . 1 . . O
  O25 0.8645(2) 0.70311(18) 0.06672(17) 0.0347(6) Uani d . 1 . . O
  C21 1.0986(3) 0.7032(2) 0.2407(3) 0.0258(8) Uani d . 1 . . C
  C22 1.0367(3) 0.6416(2) 0.3342(3) 0.0288(8) Uani d . 1 . . C
  C23 0.9141(3) 0.6013(3) 0.3382(3) 0.0287(8) Uani d . 1 . . C
  C24 0.8550(3) 0.6231(3) 0.2486(3) 0.0288(8) Uani d . 1 . . C
  C25 0.9176(3) 0.6836(3) 0.1558(3) 0.0274(8) Uani d . 1 . . C
  C26 1.0403(3) 0.7247(2) 0.1511(3) 0.0277(8) Uani d . 1 . . C
  C27 1.2329(3) 0.7409(3) 0.2413(3) 0.0298(8) Uani d . 1 . . C
  N51 0.0520(2) 0.2079(2) 0.4248(2) 0.0320(7) Uani d . 1 . . N
  C52 0.0383(3) 0.3059(3) 0.4151(3) 0.0376(9) Uani d . 1 . . C
  C53 0.1485(3) 0.3548(3) 0.4148(2) 0.0315(8) Uani d . 1 . . C
  C54 0.2842(3) 0.3002(3) 0.4253(2) 0.0263(8) Uani d . 1 . . C
  C55 0.2989(3) 0.1994(3) 0.4337(2) 0.0325(8) Uani d . 1 . . C
  C56 0.1821(3) 0.1556(3) 0.4336(2) 0.0314(8) Uani d . 1 . . C
  N61 0.6401(2) 0.4447(2) 0.4211(2) 0.0316(7) Uani d . 1 . . N
  C62 0.6441(3) 0.3405(3) 0.4625(3) 0.0337(9) Uani d . 1 . . C
  C63 0.5325(3) 0.2898(3) 0.4657(2) 0.0325(8) Uani d . 1 . . C
  C64 0.4068(3) 0.3500(3) 0.4253(2) 0.0266(8) Uani d . 1 . . C
  C65 0.4016(3) 0.4588(3) 0.3832(2) 0.0315(8) Uani d . 1 . . C
  C66 0.5183(3) 0.5035(3) 0.3817(3) 0.0327(8) Uani d . 1 . . C
  N31 -0.8410(2) 0.0180(2) 0.2197(2) 0.0314(7) Uani d . 1 . . N
  C32 -0.8992(3) -0.0570(3) 0.2990(3) 0.0331(9) Uani d . 1 . . C
  C33 -1.0221(3) -0.0928(3) 0.2957(3) 0.0294(8) Uani d . 1 . . C
  C34 -1.0900(3) -0.0484(2) 0.2042(3) 0.0266(8) Uani d . 1 . . C
  C35 -1.0304(3) 0.0304(3) 0.1226(3) 0.0290(8) Uani d . 1 . . C
  C36 -0.9081(3) 0.0618(3) 0.1329(3) 0.0309(8) Uani d . 1 . . C
  N41 -1.4634(2) -0.1513(2) 0.1670(2) 0.0322(7) Uani d . 1 . . N
  C42 -1.3782(3) -0.1000(3) 0.0886(3) 0.0339(9) Uani d . 1 . . C
  C43 -1.2601(3) -0.0654(3) 0.0979(3) 0.0311(8) Uani d . 1 . . C
  C44 -1.2197(3) -0.0856(2) 0.1929(3) 0.0272(8) Uani d . 1 . . C
  C45 -1.3065(3) -0.1409(2) 0.2751(3) 0.0291(8) Uani d . 1 . . C
  C46 -1.4255(3) -0.1715(3) 0.2592(3) 0.0323(8) Uani d . 1 . . C
  N71 0.0464(2) 0.3541(2) 0.1317(2) 0.0329(7) Uani d . 1 . . N
  C72 0.0400(3) 0.4545(3) 0.1141(3) 0.0343(9) Uani d . 1 . . C
  C73 0.1551(3) 0.5004(3) 0.1129(2) 0.0314(8) Uani d . 1 . . C
  C74 0.2865(3) 0.4398(3) 0.1319(2) 0.0271(8) Uani d . 1 . . C
  C75 0.2931(3) 0.3352(3) 0.1537(2) 0.0309(8) Uani d . 1 . . C
  C76 0.1728(3) 0.2958(3) 0.1529(3) 0.0340(9) Uani d . 1 . . C
  N81 0.6557(2) 0.5788(2) 0.1093(2) 0.0334(7) Uani d . 1 . . N
  C82 0.6538(3) 0.4747(3) 0.1597(3) 0.0342(9) Uani d . 1 . . C
  C83 0.5381(3) 0.4261(3) 0.1701(3) 0.0311(8) Uani d . 1 . . C
  C84 0.4142(3) 0.4879(3) 0.1262(2) 0.0272(8) Uani d . 1 . . C
  C85 0.4148(3) 0.5956(3) 0.0739(3) 0.0329(9) Uani d . 1 . . C
  C86 0.5355(3) 0.6379(3) 0.0684(3) 0.0352(9) Uani d . 1 . . C
  H12 -0.6646 0.0545 0.2143 0.051 Uiso calc R 1 . . H
  H13 -0.1006 0.1337 0.4449 0.055 Uiso calc R 1 . . H
  H15 -0.1014 0.2939 0.1020 0.049 Uiso calc R 1 . . H
  H12A -0.3888 0.0380 0.4371 0.034 Uiso calc R 1 . . H
  H14 -0.0868 0.2187 0.2725 0.033 Uiso calc R 1 . . H
  H16 -0.3819 0.1731 0.1287 0.032 Uiso calc R 1 . . H
  H22 1.3604 0.8184 0.1542 0.054 Uiso calc R 1 . . H
  H23 0.7862 0.5186 0.4229 0.054 Uiso calc R 1 . . H
  H25 0.8015 0.6650 0.0785 0.052 Uiso calc R 1 . . H
  H22A 1.0781 0.6271 0.3951 0.035 Uiso calc R 1 . . H
  H24 0.7708 0.5962 0.2510 0.035 Uiso calc R 1 . . H
  H26 1.0831 0.7667 0.0875 0.033 Uiso calc R 1 . . H
  H52 -0.0532 0.3442 0.4079 0.045 Uiso calc R 1 . . H
  H53 0.1327 0.4248 0.4076 0.038 Uiso calc R 1 . . H
  H55 0.3894 0.1599 0.4396 0.039 Uiso calc R 1 . . H
  H56 0.1947 0.0859 0.4401 0.038 Uiso calc R 1 . . H
  H62 0.7287 0.2983 0.4916 0.040 Uiso calc R 1 . . H
  H63 0.5419 0.2152 0.4950 0.039 Uiso calc R 1 . . H
  H65 0.3174 0.5027 0.3553 0.038 Uiso calc R 1 . . H
  H66 0.5124 0.5779 0.3519 0.039 Uiso calc R 1 . . H
  H32 -0.8541 -0.0879 0.3615 0.040 Uiso calc R 1 . . H
  H33 -1.0595 -0.1466 0.3546 0.035 Uiso calc R 1 . . H
  H35 -1.0733 0.0632 0.0592 0.035 Uiso calc R 1 . . H
  H36 -0.8699 0.1171 0.0757 0.037 Uiso calc R 1 . . H
  H42 -1.4008 -0.0867 0.0227 0.041 Uiso calc R 1 . . H
  H43 -1.2051 -0.0272 0.0390 0.037 Uiso calc R 1 . . H
  H45 -1.2841 -0.1575 0.3420 0.035 Uiso calc R 1 . . H
  H46 -1.4835 -0.2089 0.3164 0.039 Uiso calc R 1 . . H
  H72 -0.0489 0.4968 0.1017 0.041 Uiso calc R 1 . . H
  H73 0.1447 0.5723 0.0993 0.038 Uiso calc R 1 . . H
  H75 0.3800 0.2904 0.1692 0.037 Uiso calc R 1 . . H
  H76 0.1800 0.2235 0.1682 0.041 Uiso calc R 1 . . H
  H82 0.7374 0.4318 0.1901 0.041 Uiso calc R 1 . . H
  H83 0.5425 0.3518 0.2066 0.037 Uiso calc R 1 . . H
  H85 0.3330 0.6401 0.0419 0.039 Uiso calc R 1 . . H
  H86 0.5332 0.7121 0.0341 0.042 Uiso calc R 1 . . H
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
  O11 0.0300(12) 0.0381(16) 0.0362(16) -0.0157(11) 0.0019(11) -0.0145(13)
  O12 0.0248(12) 0.0357(15) 0.0426(17) -0.0125(10) -0.0049(10) -0.0149(13)
  O13 0.0310(13) 0.0455(17) 0.0336(15) -0.0150(11) -0.0028(10) -0.0142(13)
  O15 0.0299(12) 0.0329(15) 0.0320(15) -0.0146(10) -0.0013(10) -0.0082(12)
  C11 0.0223(16) 0.021(2) 0.033(2) -0.0016(14) -0.0039(15) -0.0100(17)
  C12 0.0239(16) 0.027(2) 0.032(2) -0.0045(14) 0.0025(14) -0.0113(17)
  C13 0.0251(17) 0.030(2) 0.035(2) -0.0040(14) -0.0059(15) -0.0170(18)
  C14 0.0229(16) 0.027(2) 0.032(2) -0.0080(14) -0.0005(14) -0.0114(18)
  C15 0.0240(17) 0.023(2) 0.033(2) -0.0049(14) 0.0022(15) -0.0084(17)
  C16 0.0240(16) 0.024(2) 0.035(2) -0.0033(14) -0.0069(14) -0.0135(18)
  C17 0.0247(17) 0.029(2) 0.039(2) -0.0025(15) -0.0048(16) -0.019(2)
  O21 0.0326(12) 0.0409(16) 0.0341(16) -0.0111(11) -0.0083(11) -0.0113(13)
  O22 0.0286(12) 0.0417(16) 0.0399(17) -0.0166(11) -0.0002(10) -0.0168(13)
  O23 0.0323(13) 0.0423(16) 0.0349(16) -0.0195(11) 0.0002(10) -0.0131(13)
  O25 0.0317(13) 0.0406(16) 0.0338(15) -0.0142(10) -0.0040(10) -0.0143(13)
  C21 0.0243(16) 0.024(2) 0.032(2) -0.0058(14) -0.0057(14) -0.0129(17)
  C22 0.0255(17) 0.028(2) 0.034(2) -0.0008(14) -0.0071(15) -0.0146(18)
  C23 0.0249(17) 0.029(2) 0.030(2) -0.0078(14) 0.0011(15) -0.0095(18)
  C24 0.0214(16) 0.028(2) 0.037(2) -0.0089(14) -0.0021(15) -0.0120(18)
  C25 0.0252(17) 0.027(2) 0.032(2) -0.0049(14) -0.0046(15) -0.0139(18)
  C26 0.0239(16) 0.026(2) 0.032(2) -0.0043(14) 0.0031(14) -0.0131(17)
  C27 0.0287(18) 0.025(2) 0.033(2) -0.0053(15) 0.0018(16) -0.0114(19)
  N51 0.0275(15) 0.0331(19) 0.0353(19) -0.0069(13) -0.0021(12) -0.0138(15)
  C52 0.0255(17) 0.039(3) 0.050(3) -0.0057(16) -0.0006(15) -0.020(2)
  C53 0.0267(17) 0.030(2) 0.041(2) -0.0071(15) 0.0002(15) -0.0180(18)
  C54 0.0257(17) 0.028(2) 0.023(2) -0.0043(14) -0.0021(13) -0.0089(17)
  C55 0.0286(17) 0.034(2) 0.033(2) -0.0038(15) -0.0021(14) -0.0138(19)
  C56 0.0311(18) 0.030(2) 0.036(2) -0.0098(15) -0.0011(15) -0.0150(18)
  N61 0.0306(15) 0.0308(19) 0.0348(19) -0.0095(13) -0.0004(12) -0.0139(15)
  C62 0.0254(17) 0.040(2) 0.034(2) -0.0043(15) -0.0053(14) -0.0139(19)
  C63 0.0288(17) 0.033(2) 0.033(2) -0.0089(15) 0.0003(15) -0.0107(18)
  C64 0.0253(17) 0.031(2) 0.027(2) -0.0075(15) -0.0007(14) -0.0149(18)
  C65 0.0260(17) 0.035(2) 0.035(2) -0.0040(15) -0.0022(14) -0.0174(19)
  C66 0.0316(18) 0.030(2) 0.038(2) -0.0092(15) 0.0012(15) -0.0154(18)
  N31 0.0265(14) 0.0320(18) 0.038(2) -0.0049(12) -0.0019(13) -0.0166(16)
  C32 0.0297(18) 0.036(2) 0.034(2) -0.0065(16) -0.0037(15) -0.0147(19)
  C33 0.0297(17) 0.029(2) 0.028(2) -0.0061(15) -0.0004(15) -0.0111(18)
  C34 0.0232(16) 0.025(2) 0.034(2) -0.0027(14) -0.0006(14) -0.0159(18)
  C35 0.0281(17) 0.031(2) 0.030(2) -0.0075(15) -0.0038(14) -0.0129(18)
  C36 0.0275(17) 0.034(2) 0.035(2) -0.0078(15) 0.0027(15) -0.0183(19)
  N41 0.0291(15) 0.0354(18) 0.0350(19) -0.0056(13) 0.0014(13) -0.0182(16)
  C42 0.0282(17) 0.040(2) 0.036(2) -0.0087(16) 0.0004(15) -0.0182(19)
  C43 0.0305(18) 0.032(2) 0.031(2) -0.0095(15) 0.0019(15) -0.0137(18)
  C44 0.0227(16) 0.025(2) 0.035(2) -0.0021(14) 0.0011(14) -0.0153(18)
  C45 0.0266(17) 0.029(2) 0.032(2) -0.0053(14) -0.0020(15) -0.0125(18)
  C46 0.0306(18) 0.032(2) 0.039(2) -0.0121(15) 0.0040(16) -0.0177(19)
  N71 0.0316(15) 0.0315(19) 0.0314(18) -0.0107(13) -0.0017(12) -0.0080(15)
  C72 0.0217(16) 0.036(2) 0.047(2) -0.0046(15) -0.0004(15) -0.019(2)
  C73 0.0250(17) 0.031(2) 0.041(2) -0.0068(15) -0.0002(14) -0.0178(19)
  C74 0.0268(17) 0.030(2) 0.025(2) -0.0092(15) 0.0016(14) -0.0112(17)
  C75 0.0257(17) 0.033(2) 0.035(2) -0.0085(15) -0.0031(14) -0.0137(19)
  C76 0.0347(19) 0.028(2) 0.040(2) -0.0091(16) -0.0039(16) -0.0126(18)
  N81 0.0298(15) 0.036(2) 0.0367(19) -0.0088(13) -0.0035(13) -0.0162(16)
  C82 0.0316(18) 0.038(2) 0.037(2) -0.0077(16) -0.0032(15) -0.018(2)
  C83 0.0244(17) 0.032(2) 0.040(2) -0.0048(15) -0.0001(14) -0.0186(19)
  C84 0.0214(16) 0.033(2) 0.031(2) -0.0061(14) 0.0020(14) -0.0175(18)
  C85 0.0287(17) 0.031(2) 0.038(2) -0.0062(15) -0.0076(15) -0.0118(19)
  C86 0.0355(19) 0.033(2) 0.037(2) -0.0107(16) -0.0045(16) -0.0124(19)
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
  O11 C17 . 1.215(4) yes
  O12 C17 . 1.334(4) yes
  O13 C13 . 1.375(4) yes
  O15 C15 . 1.371(4) yes
  C11 C16 . 1.386(4) no
  C11 C12 . 1.402(4) no
  C11 C17 . 1.498(4) no
  C12 C13 . 1.386(4) no
  C13 C14 . 1.382(5) no
  C14 C15 . 1.394(4) no
  C15 C16 . 1.381(4) no
  O21 C27 . 1.216(4) yes
  O22 C27 . 1.332(4) yes
  O23 C23 . 1.358(4) yes
  O25 C25 . 1.362(4) yes
  C21 C22 . 1.392(4) no
  C21 C26 . 1.385(4) no
  C21 C27 . 1.494(4) no
  C22 C23 . 1.391(4) no
  C23 C24 . 1.387(4) no
  C24 C25 . 1.385(5) no
  C25 C26 . 1.396(4) no
  N51 C52 . 1.335(4) no
  N51 C56 . 1.340(4) no
  C52 C53 . 1.373(4) no
  C53 C54 . 1.398(4) no
  C54 C55 . 1.380(4) no
  C54 C64 . 1.486(4) no
  C55 C56 . 1.386(4) no
  N61 C62 . 1.333(4) no
  N61 C66 . 1.350(4) no
  C62 C63 . 1.389(4) no
  C63 C64 . 1.390(4) no
  C64 C65 . 1.393(4) no
  C65 C66 . 1.385(4) no
  N31 C32 . 1.329(4) no
  N31 C36 . 1.340(4) no
  C32 C33 . 1.389(4) no
  C33 C34 . 1.399(4) no
  C34 C35 . 1.378(4) no
  C34 C44 . 1.500(4) no
  C35 C36 . 1.385(4) no
  N41 C42 . 1.335(4) no
  N41 C46 . 1.343(4) no
  C42 C43 . 1.366(4) no
  C43 C44 . 1.391(4) no
  C44 C45 . 1.390(4) no
  C45 C46 . 1.382(4) no
  N71 C72 . 1.337(4) no
  N71 C76 . 1.342(4) no
  C72 C73 . 1.384(4) no
  C73 C74 . 1.393(4) no
  C74 C75 . 1.380(4) no
  C74 C84 . 1.492(4) no
  C75 C76 . 1.383(4) no
  N81 C82 . 1.341(4) no
  N81 C86 . 1.344(4) no
  C82 C83 . 1.378(4) no
  C83 C84 . 1.396(4) no
  C84 C85 . 1.385(4) no
  C85 C86 . 1.385(4) no