#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/22/2012258.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2012258
loop_
_publ_author_name
'Cowan, John A.'
'Howard, Judith A. K.'
'Leech, Michael A.'
_publ_section_title
;
 Interpenetrating supramolecular lattices in
 4,4'-bipyridine--2,3,5,6-tetrahydroxy-1,4-benzoquinone (3/2)
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1196
_journal_page_last               1198
_journal_paper_doi               10.1107/S0108270101011647
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          '3C10 H8 N2, 2C6 H4 O6'
_chemical_formula_moiety         '3C10 H8 N2, 2C6 H4 O6'
_chemical_formula_sum            'C42 H32 N6 O12'
_chemical_formula_weight         812.74
_chemical_name_systematic
;
4,4'-bipyridine--tetrahydroxybenzoquinone (3/2)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                109.164(5)
_cell_angle_beta                 92.476(5)
_cell_angle_gamma                111.074(5)
_cell_formula_units_Z            1
_cell_length_a                   8.8856(8)
_cell_length_b                   9.0728(9)
_cell_length_c                   12.9288(11)
_cell_measurement_reflns_used    910
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.07
_cell_measurement_theta_min      9.31
_cell_volume                     903.17(15)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full .995
_diffrn_measured_fraction_theta_max .995
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0374
_diffrn_reflns_av_sigmaI/netI    .0673
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9859
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.70
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .112
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  .754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             422
_exptl_crystal_size_max          .6
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .3
_refine_diff_density_max         .265
_refine_diff_density_min         -.247
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          .0715
_refine_ls_R_factor_gt           .0377
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.02P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0666
_reflns_number_gt                2628
_reflns_number_total             4127
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd1161.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        903.17(14)
_cod_database_code               2012258
_cod_database_fobs_code          2012258
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 .89557(18) .82743(19) .47812(12) .0173(3) Uani d . 1 . . C
O1 .80029(12) .68015(13) .46000(8) .0227(3) Uani d . 1 . . O
C2 .86208(18) .92017(19) .41054(12) .0176(3) Uani d . 1 . . C
O2 .72974(13) .83418(14) .32649(9) .0249(3) Uani d . 1 . . O
H2 .6954(19) .728(2) .3104(13) .030 Uiso d . 1 . . H
C3 .95777(18) 1.08520(19) .43304(12) .0179(3) Uani d . 1 . . C
O3 .92496(13) 1.16916(13) .37192(9) .0236(3) Uani d . 1 . . O
H3 1.0132(18) 1.278(2) .3861(12) .028 Uiso d . 1 . . H
C4 .66918(18) .56848(18) .04832(12) .0177(3) Uani d . 1 . . C
O4 .81671(12) .63116(13) .08719(9) .0248(3) Uani d . 1 . . O
C5 .54347(18) .49434(18) .10817(12) .0168(3) Uani d . 1 . . C
O5 .60280(12) .49760(13) .20800(8) .0200(3) Uani d . 1 . . O
H5 .5311(18) .421(2) .2284(12) .024 Uiso d . 1 . . H
C6 .38340(18) .43229(18) .06343(12) .0169(3) Uani d . 1 . . C
O6 .26616(13) .36837(13) .11753(9) .0229(3) Uani d . 1 . . O
H6 .1592(19) .3159(19) .0754(13) .028 Uiso d . 1 . . H
N1 .11089(15) -.52917(15) .36960(10) .0211(3) Uani d . 1 . . N
C10 .2677(2) -.4212(2) .41080(13) .0241(4) Uani d . 1 . . C
H10 .3327(18) -.4490(19) .4552(13) .029 Uiso d . 1 . . H
C11 .3392(2) -.2698(2) .39293(13) .0213(4) Uani d . 1 . . C
H11 .4556(18) -.2026(18) .4251(12) .026 Uiso d . 1 . . H
C12 .24512(18) -.22625(18) .32817(12) .0176(3) Uani d . 1 . . C
C13 .31481(18) -.06245(18) .30901(12) .0170(3) Uani d . 1 . . C
C14 .4832(2) .0273(2) .32274(13) .0225(4) Uani d . 1 . . C
H14 .5627(18) -.0103(19) .3446(12) .027 Uiso d . 1 . . H
C15 .5411(2) .1781(2) .30252(13) .0224(4) Uani d . 1 . . C
H15 .6599(19) .2402(19) .3125(12) .027 Uiso d . 1 . . H
N2 .44245(15) .24380(15) .27038(10) .0205(3) Uani d . 1 . . N
C16 .28094(19) .15788(19) .25806(12) .0203(4) Uani d . 1 . . C
H16 .2088(17) .2016(18) .2328(12) .024 Uiso d . 1 . . H
C17 .21196(19) .00584(19) .27529(12) .0194(4) Uani d . 1 . . C
H17 .0941(18) -.0507(18) .2634(12) .023 Uiso d . 1 . . H
C18 .08324(19) -.33958(19) .28373(13) .0195(4) Uani d . 1 . . C
H18 .0077(18) -.3228(18) .2364(12) .023 Uiso d . 1 . . H
C19 .0219(2) -.4879(2) .30598(13) .0207(4) Uani d . 1 . . C
H19 -.0942(18) -.5659(19) .2762(12) .025 Uiso d . 1 . . H
N3 -.06220(15) .20248(16) .04592(10) .0234(3) Uani d . 1 . . N
C20 -.1387(2) .0781(2) .08389(14) .0258(4) Uani d . 1 . . C
H20 -.0655(18) .0469(19) .1263(12) .031 Uiso d . 1 . . H
C21 -.30727(19) -.0022(2) .06882(13) .0247(4) Uani d . 1 . . C
H21 -.3562(18) -.0915(19) .1031(12) .030 Uiso d . 1 . . H
C22 -.40869(18) .04258(18) .01029(12) .0194(3) Uani d . 1 . . C
C23 -.32893(19) .1733(2) -.02812(13) .0219(4) Uani d . 1 . . C
H23 -.3991(17) .2072(18) -.0750(12) .026 Uiso d . 1 . . H
C24 -.15926(19) .2476(2) -.00853(13) .0231(4) Uani d . 1 . . C
H24 -.1011(18) .3389(19) -.0339(12) .028 Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O1 C1 C3 . 2_776 121.26(12)
O1 C1 C2 . . 119.76(13)
C3 C1 C2 2_776 . 118.97(12)
C3 C2 O2 . . 121.13(13)
C3 C2 C1 . . 121.26(13)
O2 C2 C1 . . 117.59(13)
C2 O2 H2 . . 111.6(11)
O3 C3 C2 . . 120.81(13)
O3 C3 C1 . 2_776 119.47(13)
C2 C3 C1 . 2_776 119.66(12)
C3 O3 H3 . . 112.8(9)
O4 C4 C5 . . 122.15(13)
O4 C4 C6 . 2_665 118.59(13)
C5 C4 C6 . 2_665 119.26(12)
C6 C5 O5 . . 125.16(13)
C6 C5 C4 . . 119.71(13)
O5 C5 C4 . . 115.12(12)
C5 O5 H5 . . 111.8(9)
O6 C6 C5 . . 121.00(13)
O6 C6 C4 . 2_665 118.01(12)
C5 C6 C4 . 2_665 120.98(13)
C6 O6 H6 . . 114.2(9)
C10 N1 C19 . . 116.96(13)
N1 C10 C11 . . 123.47(15)
N1 C10 H10 . . 118.1(9)
C11 C10 H10 . . 118.4(9)
C10 C11 C12 . . 119.25(15)
C10 C11 H11 . . 116.4(8)
C12 C11 H11 . . 124.3(8)
C18 C12 C11 . . 117.35(14)
C18 C12 C13 . . 121.28(13)
C11 C12 C13 . . 121.36(13)
C14 C13 C17 . . 117.18(13)
C14 C13 C12 . . 121.89(13)
C17 C13 C12 . . 120.93(13)
C13 C14 C15 . . 119.41(14)
C13 C14 H14 . . 123.1(9)
C15 C14 H14 . . 117.5(9)
N2 C15 C14 . . 123.41(15)
N2 C15 H15 . . 117.9(8)
C14 C15 H15 . . 118.7(8)
C16 N2 C15 . . 116.98(12)
N2 C16 C17 . . 123.66(14)
N2 C16 H16 . . 117.8(8)
C17 C16 H16 . . 118.5(8)
C16 C17 C13 . . 119.34(15)
C16 C17 H17 . . 119.3(8)
C13 C17 H17 . . 121.4(8)
C19 C18 C12 . . 119.53(14)
C19 C18 H18 . . 116.4(8)
C12 C18 H18 . . 124.1(8)
N1 C19 C18 . . 123.42(15)
N1 C19 H19 . . 117.5(8)
C18 C19 H19 . . 119.1(8)
C24 N3 C20 . . 116.28(13)
N3 C20 C21 . . 123.58(15)
N3 C20 H20 . . 116.0(8)
C21 C20 H20 . . 120.5(8)
C20 C21 C22 . . 120.20(15)
C20 C21 H21 . . 119.0(8)
C22 C21 H21 . . 120.7(8)
C21 C22 C23 . . 116.14(14)
C21 C22 C22 . 2_455 122.34(16)
C23 C22 C22 . 2_455 121.52(17)
C24 C23 C22 . . 119.76(15)
C24 C23 H23 . . 121.3(8)
C22 C23 H23 . . 118.8(8)
N3 C24 C23 . . 124.02(15)
N3 C24 H24 . . 114.7(8)
C23 C24 H24 . . 121.3(9)
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 O1 . 1.2333(16) ?
C1 C3 2_776 1.475(2) ?
C1 C2 . 1.4833(19) ?
C2 C3 . 1.3515(19) ?
C2 O2 . 1.3585(17) ?
O2 H2 . .844(16) ?
C3 O3 . 1.3509(16) ?
C3 C1 2_776 1.475(2) ?
O3 H3 . .965(15) ?
C4 O4 . 1.2304(17) ?
C4 C5 . 1.475(2) ?
C4 C6 2_665 1.496(2) ?
C5 C6 . 1.347(2) ?
C5 O5 . 1.3600(16) ?
O5 H5 . .882(15) ?
C6 O6 . 1.3438(16) ?
C6 C4 2_665 1.496(2) ?
O6 H6 . .941(15) ?
N1 C10 . 1.3406(19) ?
N1 C19 . 1.3419(18) ?
C10 C11 . 1.392(2) ?
C10 H10 . .948(15) ?
C11 C12 . 1.396(2) ?
C11 H11 . .978(15) ?
C12 C18 . 1.390(2) ?
C12 C13 . 1.4989(19) ?
C13 C14 . 1.393(2) ?
C13 C17 . 1.3997(19) ?
C14 C15 . 1.395(2) ?
C14 H14 . .956(15) ?
C15 N2 . 1.3428(18) ?
C15 H15 . .980(15) ?
N2 C16 . 1.3368(18) ?
C16 C17 . 1.391(2) ?
C16 H16 . .963(14) ?
C17 H17 . .965(14) ?
C18 C19 . 1.390(2) ?
C18 H18 . .974(14) ?
C19 H19 . .987(14) ?
N3 C24 . 1.3409(19) ?
N3 C20 . 1.3482(19) ?
C20 C21 . 1.382(2) ?
C20 H20 . 1.004(14) ?
C21 C22 . 1.399(2) ?
C21 H21 . 1.020(14) ?
C22 C23 . 1.403(2) ?
C22 C22 2_455 1.492(3) ?
C23 C24 . 1.384(2) ?
C23 H23 . 1.039(14) ?
C24 H24 . .973(14) ?
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
_geom_hbond_publ_flag
O2 H2 O5 . .84(2) 1.91(2) 2.692(2) 153(2) y
O3 H3 N1 1_675 .97(2) 1.74(2) 2.651(2) 155.0(10) y
O5 H5 N2 . .88(2) 1.79(2) 2.635(2) 161.0(10) y
O6 H6 N3 . .94(2) 1.82(2) 2.707(2) 157.0(10) y
C14 H14 O2 1_545 .94(2) 2.36(2) 3.268(2) 158.0(10) y
C16 H16 O6 . .960(10) 2.400(10) 3.066(2) 126.0(10) y
C18 H18 O4 1_445 .970(10) 2.34(2) 3.274(2) 162.0(10) y
