#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/58/2015879.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_2015879
loop_
_publ_author_name
'Lou, Ben-Yong'
'Huang, Yan-Bin'
_publ_section_title
;
 4,4'-Bipyridyl N,N'-dioxide--3-hydroxy-2-naphthoic acid
 (1/2)
;
_journal_coeditor_code           AV3073
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o246
_journal_page_last               o248
_journal_paper_doi               10.1107/S0108270107009717
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C10 H8 N2 O2 , 2C11 H8 O3'
_chemical_formula_moiety         'C10 H8 N2 O2 , 2C11 H8 O3'
_chemical_formula_sum            'C32 H24 N2 O8'
_chemical_formula_weight         564.54
_chemical_name_systematic
;
4,4'-Bipyridyl N,N'-dioxide--3-hydroxy-2-naphthoic acid (1/2)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.820(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7800(16)
_cell_length_b                   11.8800(11)
_cell_length_c                   11.4700(15)
_cell_measurement_reflns_used    2490
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      2.0823
_cell_volume                     1333.2(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2000)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 14.6306
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Make, Model'
_diffrn_measurement_method       'CCD profile fitting'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9907
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0668P)²+0.1631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                2226
_reflns_number_total             3038
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            av3073.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015879
_cod_database_fobs_code          2015879
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
O O1 0.18458(15) 0.58214(12) 0.09720(13) 0.0740(4) Uani d . 1
O O2 0.23290(15) 0.40082(11) 0.14199(12) 0.0699(4) Uani d . 1
H H2 0.1983 0.3959 0.0615 0.084 Uiso calc R 1
O O3 0.21240(16) 0.71931(11) 0.28290(15) 0.0727(4) Uani d . 1
H H3 0.1944 0.6991 0.2073 0.087 Uiso calc R 1
O O4 0.14552(17) 0.32739(12) -0.08157(12) 0.0787(4) Uani d . 1
N N1 0.10763(15) 0.37778(12) -0.19440(12) 0.0516(4) Uani d . 1
C C1 0.22627(17) 0.50500(15) 0.17531(16) 0.0530(4) Uani d . 1
C C2 0.27113(15) 0.52152(13) 0.31465(15) 0.0452(4) Uani d . 1
C C3 0.26163(16) 0.62990(14) 0.36358(18) 0.0518(4) Uani d . 1
C C4 0.30015(17) 0.64514(15) 0.49205(18) 0.0563(5) Uani d . 1
H H4 0.2940 0.7180 0.5234 0.068 Uiso calc R 1
C C5 0.3877(2) 0.5660(2) 0.7132(2) 0.0692(6) Uani d . 1
H H5 0.3831 0.6378 0.7476 0.083 Uiso calc R 1
C C6 0.4312(2) 0.4754(2) 0.79280(19) 0.0758(6) Uani d . 1
H H6 0.4566 0.4851 0.8821 0.091 Uiso calc R 1
C C7 0.43941(19) 0.3681(2) 0.74570(18) 0.0692(6) Uani d . 1
H H7 0.4696 0.3057 0.8027 0.083 Uiso calc R 1
C C8 0.40393(16) 0.35361(16) 0.61795(16) 0.0562(4) Uani d . 1
H H8 0.4099 0.2809 0.5861 0.067 Uiso calc R 1
C C9 0.31936(15) 0.43305(13) 0.39928(15) 0.0453(4) Uani d . 1
H H9 0.3267 0.3609 0.3670 0.054 Uiso calc R 1
C C10 0.35824(15) 0.44576(13) 0.53190(15) 0.0456(4) Uani d . 1
C C11 0.34909(16) 0.55425(15) 0.57941(17) 0.0512(4) Uani d . 1
C C12 0.09075(19) 0.31387(15) -0.29611(16) 0.0565(4) Uani d . 1
H H12 0.1076 0.2352 -0.2850 0.068 Uiso calc R 1
C C13 0.04963(17) 0.36008(14) -0.41559(15) 0.0506(4) Uani d . 1
H H13 0.0389 0.3131 -0.4862 0.061 Uiso calc R 1
C C14 0.08520(18) 0.48919(14) -0.20824(16) 0.0534(4) Uani d . 1
H H14 0.0987 0.5343 -0.1355 0.064 Uiso calc R 1
C C15 0.04288(17) 0.53811(14) -0.32708(14) 0.0479(4) Uani d . 1
H H15 0.0266 0.6169 -0.3356 0.057 Uiso calc R 1
C C16 0.02329(14) 0.47465(13) -0.43554(14) 0.0393(3) Uani d . 1
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O2 H2 . 109.5 ?
C3 O3 H3 . 109.5 ?
O4 N1 C12 . 117.92(14) yes
O4 N1 C14 . 121.81(14) yes
C12 N1 C14 . 120.27(14) ?
O1 C1 O2 . 122.83(17) yes
O1 C1 C2 . 122.98(17) yes
O2 C1 C2 . 114.18(14) yes
C9 C2 C3 . 118.72(15) ?
C9 C2 C1 . 121.16(15) ?
C3 C2 C1 . 120.10(15) ?
O3 C3 C4 . 119.04(16) ?
O3 C3 C2 . 120.60(16) ?
C4 C3 C2 . 120.35(16) ?
C3 C4 C11 . 121.13(16) ?
C3 C4 H4 . 119.4 ?
C11 C4 H4 . 119.4 ?
C6 C5 C11 . 120.7(2) ?
C6 C5 H5 . 119.7 ?
C11 C5 H5 . 119.7 ?
C5 C6 C7 . 121.37(19) ?
C5 C6 H6 . 119.3 ?
C7 C6 H6 . 119.3 ?
C8 C7 C6 . 119.7(2) ?
C8 C7 H7 . 120.2 ?
C6 C7 H7 . 120.2 ?
C7 C8 C10 . 120.73(19) ?
C7 C8 H8 . 119.6 ?
C10 C8 H8 . 119.6 ?
C2 C9 C10 . 122.27(15) ?
C2 C9 H9 . 118.9 ?
C10 C9 H9 . 118.9 ?
C9 C10 C8 . 121.96(16) ?
C9 C10 C11 . 118.41(15) ?
C8 C10 C11 . 119.62(16) ?
C4 C11 C5 . 122.94(18) ?
C4 C11 C10 . 119.10(16) ?
C5 C11 C10 . 117.95(17) ?
N1 C12 C13 . 120.96(16) ?
N1 C12 H12 . 119.5 ?
C13 C12 H12 . 119.5 ?
C12 C13 C16 . 121.11(15) ?
C12 C13 H13 . 119.4 ?
C16 C13 H13 . 119.4 ?
N1 C14 C15 . 120.22(15) ?
N1 C14 H14 . 119.9 ?
C15 C14 H14 . 119.9 ?
C14 C15 C16 . 121.38(15) ?
C14 C15 H15 . 119.3 ?
C16 C15 H15 . 119.3 ?
C13 C16 C15 . 116.06(14) ?
C13 C16 C16 3_564 121.65(17) ?
C15 C16 C16 3_564 122.29(17) ?
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
O1 C1 . 1.227(2) yes
O2 C1 . 1.306(2) yes
O2 H2 . 0.8400 ?
O3 C3 . 1.362(2) yes
O3 H3 . 0.8400 ?
O4 N1 . 1.3252(17) yes
N1 C12 . 1.339(2) yes
N1 C14 . 1.343(2) yes
C1 C2 . 1.476(2) ?
C2 C9 . 1.376(2) ?
C2 C3 . 1.425(2) ?
C3 C4 . 1.365(3) ?
C4 C11 . 1.416(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.361(3) ?
C5 C11 . 1.418(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.402(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.361(3) ?
C7 H7 . 0.9500 ?
C8 C10 . 1.417(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.406(2) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.419(2) ?
C12 C13 . 1.366(2) ?
C12 H12 . 0.9500 ?
C13 C16 . 1.390(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.372(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.393(2) ?
C15 H15 . 0.9500 ?
C16 C16 3_564 1.476(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3 O1 0.84 1.85 2.597(2) 147
O2 H2 O4 0.84 1.70 2.489(2) 155
