#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/54/2005458.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_2005458
loop_
_publ_author_name
'Coupar, P. I.'
'Ferguson, G.'
'Glidewell, C.'
_publ_section_title
;
 Hydrogen-Bonded Chains in 4,4'-Dihydroxybenzophenone--4,4'-Bipyridyl
 (1/1) and Chains of Rings in 1,3,5-Trihydroxybenzene--4,4'-Bipyridyl
 (2/3)
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2524
_journal_page_last               2528
_journal_paper_doi               10.1107/S0108270196008669
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C13 H10 O3 , C10 H8 N2'
_chemical_formula_sum            'C23 H18 N2 O3'
_chemical_formula_weight         370.39
_chemical_name_systematic
;
4,4'-Dihydroxybenzophenone--4,4'-Bipyridyl (1/1)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 110.792(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.559(2)
_cell_length_b                   7.0926(7)
_cell_length_c                   22.138(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(1)
_cell_measurement_theta_max      12.87
_cell_measurement_theta_min      8.83
_cell_volume                     3751.8(6)
_computing_cell_refinement       'SET4 and CELDIM (Enraf-Nonius, 1992)'
_computing_data_collection       'CAD4 (Enraf-Nonius, 1992)'
_computing_data_reduction
'DATRD2 in NRCVAX94 (Gabe, Le Page, Charland, Lee & White, 1989)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976), NRCVAX94, PLATON and PLUTON (Spek 1995b)'
_computing_publication_material
'NRCVAX94, SHELXL93  and WordPerfect macro PREPCIF'
_computing_structure_refinement  'NRCVAX94 and SHELXL93'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      294.0(10)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Molybdenum K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_av_sigmaI/netI    0.1179
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3376
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2
_diffrn_standards_decay_%        2.4
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  1.0
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.951
_refine_ls_goodness_of_fit_obs   1.273
_refine_ls_hydrogen_treatment    'H atoms riding (C-H 0.93, O-H 0.82\%A)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3292
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.951
_refine_ls_restrained_S_obs      1.273
_refine_ls_R_factor_all          0.1775
_refine_ls_R_factor_obs          0.0706
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0467P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1513
_refine_ls_wR_factor_obs         0.1251
_reflns_number_observed          1398
_reflns_number_total             3292
_reflns_observed_criterion       >2\s(I)
_cod_data_source_file            ab1404.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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0467P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed
to 'calc'. New tag '_refine_ls_weighting_details' was created. The
value of the new tag was set to 'w=1/[\s^2^(Fo^2^)+(0.0467P)^2^]
where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        3751.9(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2005458
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
O1 1 0.68746(10) 0.1980(5) 0.11420(13) 0.0604(9) Uani d . O
O2 1 0.40228(12) 0.9010(5) 0.2275(2) 0.0684(9) Uani d . O
O3 1 0.42771(11) 0.2269(5) 0.05463(14) 0.0789(11) Uani d . O
C3 1 0.4643(2) 0.3291(8) 0.0905(2) 0.0590(13) Uani d . C
C11 1 0.5232(2) 0.3041(7) 0.0953(2) 0.0522(12) Uani d . C
C12 1 0.5672(2) 0.3343(6) 0.1526(2) 0.0543(13) Uani d . C
C13 1 0.6217(2) 0.2973(6) 0.1585(2) 0.0534(12) Uani d . C
C14 1 0.6332(2) 0.2327(6) 0.1062(2) 0.0454(11) Uani d . C
C15 1 0.5901(2) 0.2023(7) 0.0479(2) 0.0588(13) Uani d . C
C16 1 0.5356(2) 0.2352(7) 0.0435(2) 0.0661(15) Uani d . C
C21 1 0.4499(2) 0.4791(8) 0.1286(2) 0.0510(12) Uani d . C
C22 1 0.4750(2) 0.6552(8) 0.1381(2) 0.0617(14) Uani d . C
C23 1 0.4580(2) 0.7956(7) 0.1700(2) 0.0602(13) Uani d . C
C24 1 0.4170(2) 0.7598(7) 0.1953(2) 0.0517(12) Uani d . C
C25 1 0.3918(2) 0.5853(7) 0.1865(2) 0.0563(13) Uani d . C
C26 1 0.4078(2) 0.4489(7) 0.1536(2) 0.0576(13) Uani d . C
C31 1 0.7618(2) -0.0762(6) -0.0729(2) 0.0449(11) Uani d . C
C32 1 0.7925(2) -0.0480(6) -0.0084(2) 0.0496(12) Uani d . C
C33 1 0.7664(2) 0.0164(6) 0.0323(2) 0.0513(12) Uani d . C
N34 1 0.71218(14) 0.0562(5) 0.0137(2) 0.0524(10) Uani d . N
C35 1 0.6827(2) 0.0302(7) -0.0487(2) 0.0588(13) Uani d . C
C36 1 0.7054(2) -0.0349(6) -0.0925(2) 0.0535(12) Uani d . C
C41 1 0.7878(2) -0.1491(6) -0.1190(2) 0.0439(11) Uani d . C
C42 1 0.8410(2) -0.2255(6) -0.0980(2) 0.0499(12) Uani d . C
C43 1 0.8632(2) -0.2873(6) -0.1428(2) 0.0571(12) Uani d . C
N44 1 0.8360(2) -0.2816(5) -0.2071(2) 0.0575(10) Uani d . N
C45 1 0.7851(2) -0.2084(7) -0.2267(2) 0.0618(13) Uani d . C
C46 1 0.7594(2) -0.1427(7) -0.1858(2) 0.0588(13) Uani d . C
H1 1 0.6893 0.1569 0.0804 0.091 Uiso calc R H
H2 1 0.3792 0.8617 0.2424 0.103 Uiso calc R H
H12 1 0.5598 0.3806 0.1881 0.065 Uiso calc R H
H13 1 0.6506 0.3162 0.1978 0.064 Uiso calc R H
H15 1 0.5977 0.1602 0.0122 0.071 Uiso calc R H
H16 1 0.5066 0.2104 0.0048 0.079 Uiso calc R H
H22 1 0.5038 0.6790 0.1226 0.074 Uiso calc R H
H23 1 0.4743 0.9145 0.1745 0.072 Uiso calc R H
H25 1 0.3638 0.5608 0.2031 0.068 Uiso calc R H
H26 1 0.3901 0.3322 0.1476 0.069 Uiso calc R H
H32 1 0.8307 -0.0724 0.0076 0.060 Uiso calc R H
H33 1 0.7881 0.0330 0.0757 0.062 Uiso calc R H
H35 1 0.6446 0.0575 -0.0635 0.071 Uiso calc R H
H36 1 0.6827 -0.0512 -0.1356 0.064 Uiso calc R H
H42 1 0.8617 -0.2349 -0.0541 0.060 Uiso calc R H
H43 1 0.8993 -0.3363 -0.1275 0.069 Uiso calc R H
H45 1 0.7655 -0.2010 -0.2709 0.074 Uiso calc R H
H46 1 0.7233 -0.0941 -0.2025 0.071 Uiso calc R H
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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 2 -2
2 -2 -2
3 1 5
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O3 C3 C11 119.9(4) y
O3 C3 C21 120.4(4) y
C11 C3 C21 119.7(4) y
C3 C11 C12 121.5(4) ?
C3 C11 C16 120.6(4) ?
C12 C11 C16 117.7(4) ?
C11 C12 C13 121.5(4) ?
C12 C13 C14 119.8(4) ?
O1 C14 C13 117.8(4) ?
O1 C14 C15 122.2(4) ?
C13 C14 C15 120.0(4) ?
C14 C15 C16 119.3(4) ?
C11 C16 C15 121.6(4) ?
C3 C21 C22 122.5(4) ?
C3 C21 C26 120.0(5) ?
C22 C21 C26 117.5(5) ?
C21 C22 C23 120.9(4) ?
C22 C23 C24 120.0(5) ?
O2 C24 C23 118.1(5) ?
O2 C24 C25 122.3(4) ?
C23 C24 C25 119.6(5) ?
C24 C25 C26 120.1(4) ?
C21 C26 C25 121.8(5) ?
C32 C31 C36 116.1(4) ?
C32 C31 C41 122.2(4) ?
C36 C31 C41 121.7(4) ?
C31 C32 C33 119.8(4) ?
C32 C33 N34 124.2(4) ?
C33 N34 C35 115.9(4) ?
N34 C35 C36 123.5(4) ?
C31 C36 C35 120.3(4) ?
C31 C41 C42 121.9(4) ?
C31 C41 C46 121.5(4) ?
C42 C41 C46 116.6(4) ?
C41 C42 C43 119.3(4) ?
C42 C43 N44 124.3(4) ?
C43 N44 C45 115.9(4) ?
N44 C45 C46 124.2(4) ?
C41 C46 C45 119.7(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C14 1.357(4) y
O2 C24 1.358(5) y
O3 C3 1.226(5) y
C3 C11 1.481(5) y
C3 C21 1.483(6) y
C11 C12 1.381(5) ?
C11 C16 1.383(5) ?
C12 C13 1.378(5) ?
C13 C14 1.371(5) ?
C14 C15 1.384(5) ?
C15 C16 1.380(5) ?
C21 C22 1.387(6) ?
C21 C26 1.389(5) ?
C22 C23 1.379(6) ?
C23 C24 1.376(5) ?
C24 C25 1.376(6) ?
C25 C26 1.359(5) ?
C31 C32 1.379(5) ?
C31 C36 1.382(5) ?
C31 C41 1.493(5) ?
C32 C33 1.375(5) ?
C33 N34 1.327(4) ?
N34 C35 1.331(5) ?
C35 C36 1.377(5) ?
C41 C42 1.383(5) ?
C41 C46 1.397(5) ?
C42 C43 1.376(5) ?
C43 N44 1.345(5) ?
N44 C45 1.323(5) ?
C45 C46 1.374(5) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
O3 C3 C11 C12 -145.8(5) y
O3 C3 C11 C16 29.1(7) y
C21 C3 C11 C12 34.9(6) ?
C21 C3 C11 C16 -150.3(5) ?
C16 C11 C12 C13 0.0(7) ?
C3 C11 C12 C13 175.0(4) ?
C11 C12 C13 C14 1.3(7) ?
C12 C13 C14 O1 -180.0(4) ?
C12 C13 C14 C15 -0.8(7) ?
O1 C14 C15 C16 178.1(4) ?
C13 C14 C15 C16 -0.9(7) ?
C14 C15 C16 C11 2.3(7) ?
C12 C11 C16 C15 -1.8(7) ?
C3 C11 C16 C15 -176.8(4) ?
O3 C3 C21 C22 -141.0(4) y
O3 C3 C21 C26 35.8(6) y
C11 C3 C21 C22 38.4(6) ?
C11 C3 C21 C26 -144.9(4) ?
C26 C21 C22 C23 -1.2(6) ?
C3 C21 C22 C23 175.6(4) ?
C21 C22 C23 C24 2.6(7) ?
C22 C23 C24 O2 178.7(4) ?
C22 C23 C24 C25 -2.2(6) ?
O2 C24 C25 C26 179.6(4) ?
C23 C24 C25 C26 0.6(6) ?
C24 C25 C26 C21 0.7(6) ?
C22 C21 C26 C25 -0.4(6) ?
C3 C21 C26 C25 -177.3(4) ?
C36 C31 C32 C33 0.5(6) ?
C41 C31 C32 C33 -178.9(4) ?
C31 C32 C33 N34 -0.6(7) ?
C32 C33 N34 C35 0.1(6) ?
C33 N34 C35 C36 0.4(7) ?
N34 C35 C36 C31 -0.4(7) ?
C32 C31 C36 C35 -0.1(6) ?
C41 C31 C36 C35 179.3(4) ?
C32 C31 C41 C42 12.4(6) y
C36 C31 C41 C42 -167.0(4) ?
C32 C31 C41 C46 -167.3(4) ?
C36 C31 C41 C46 13.3(6) y
C46 C41 C42 C43 0.9(6) ?
C31 C41 C42 C43 -178.9(4) ?
C41 C42 C43 N44 -1.0(7) ?
C42 C43 N44 C45 0.9(7) ?
C43 N44 C45 C46 -0.8(7) ?
N44 C45 C46 C41 0.8(7) ?
C42 C41 C46 C45 -0.8(6) ?
C31 C41 C46 C45 178.9(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21138110
