#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/71/2017173.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_2017173
loop_
_publ_author_name
'Telzhensky, Marina'
'Kaftory, Menahem'
_publ_section_title
;
 Structural effects on the solid-state photodimerization of 2-pyridone
 derivatives in inclusion compounds
;
_journal_coeditor_code           FG3097
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o314
_journal_page_last               o320
_journal_paper_doi               10.1107/S010827010901751X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H10 O4, 2C5 H5 N O'
_chemical_formula_moiety         'C14 H10 O4, 2(C5 H5 N O)'
_chemical_formula_sum            'C24 H20 N2 O6'
_chemical_formula_weight         432.42
_chemical_name_common            'Diphenic acid:pyridone'
_chemical_name_systematic
;
1,1'-Biphenyl-2,2'-dicarboxylic acid--2-(1H)-pyridone (1/2)
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.95(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5690(10)
_cell_length_b                   14.054(3)
_cell_length_c                   15.0160(10)
_cell_measurement_reflns_used    6780
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.88
_cell_measurement_theta_min      3.22
_cell_volume                     2144.6(6)
_computing_cell_refinement       'DENZO HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 2006)'
_computing_data_reduction        'DENZO HKL2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-scans'
_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  0.026
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6780
_diffrn_reflns_theta_full        25.88
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             904.0
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.348
_refine_ls_extinction_coef       0.018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0620
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1098P)²+1.1226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1794
_refine_ls_wR_factor_ref         0.1999
_reflns_number_gt                1489
_reflns_number_total             2013
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            fg3097.cif
_cod_data_source_block           I-a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_refine_ls_hydrogen_treatment' value 'refu' changed to 'refU' according
to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'refu' changed to 'refU'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2017173
_cod_database_fobs_code          2017173
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.1058(2) 0.50666(19) 0.3779(2) 0.1418(12) Uani d . 1 . .
O O2 -0.07094(18) 0.58007(13) 0.39187(16) 0.0978(7) Uani d . 1 . .
H H1O2 -0.0161 0.6197 0.4177 0.151(16) Uiso calc R 1 . .
O O3 0.09147(17) 0.71551(13) 0.46002(13) 0.0837(6) Uani d . 1 . .
N N1 0.14965(17) 0.84329(14) 0.55304(13) 0.0699(6) Uani d . 1 . .
H H1N1 0.2301 0.8341 0.5532 0.075(7) Uiso calc R 1 . .
C C1 -0.0638(2) 0.36367(17) 0.26248(15) 0.0661(6) Uani d . 1 . .
C C2 -0.1501(3) 0.2897(2) 0.22859(19) 0.0845(8) Uani d . 1 . .
H H2 -0.1271 0.2437 0.1913 0.104(10) Uiso calc R 1 . .
C C3 -0.2706(3) 0.2825(2) 0.2489(2) 0.0915(9) Uani d . 1 . .
H H3 -0.3272 0.2324 0.2249 0.100(9) Uiso calc R 1 . .
C C4 -0.3057(3) 0.3491(2) 0.3039(2) 0.0850(8) Uani d . 1 . .
H H4 -0.3865 0.3450 0.3171 0.105(9) Uiso calc R 1 . .
C C5 -0.2209(2) 0.42181(19) 0.33947(19) 0.0776(7) Uani d . 1 . .
H H5 -0.2444 0.4665 0.3778 0.091(8) Uiso calc R 1 . .
C C6 -0.1004(2) 0.43056(16) 0.31978(16) 0.0671(6) Uani d . 1 . .
C C7 -0.0121(2) 0.50949(19) 0.36342(19) 0.0803(8) Uani d . 1 . .
C C8 0.0570(2) 0.78351(16) 0.50250(16) 0.0651(6) Uani d . 1 . .
C C9 -0.0742(2) 0.80481(18) 0.50159(18) 0.0759(7) Uani d . 1 . .
H H9 -0.1425 0.7672 0.4669 0.100(9) Uiso calc R 1 . .
C C10 -0.1019(2) 0.87866(19) 0.5502(2) 0.0819(8) Uani d . 1 . .
H H10 -0.1890 0.8916 0.5480 0.118(11) Uiso calc R 1 . .
C C11 -0.0025(3) 0.93577(19) 0.6035(2) 0.0831(8) Uani d . 1 . .
H H11 -0.0216 0.9857 0.6382 0.099(9) Uiso calc R 1 . .
C C12 0.1230(2) 0.91696(19) 0.60353(18) 0.0795(7) Uani d . 1 . .
H H12 0.1912 0.9546 0.6383 0.101(9) Uiso calc R 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'
O O 0.0106 0.0060 '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'
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
_geom_angle_publ_flag
C7 O2 H1O2 . . 109.5 ?
C12 N1 C8 . . 123.85(19) ?
C12 N1 H1N1 . . 118.1 ?
C8 N1 H1N1 . . 118.1 ?
C2 C1 C6 . . 117.7(2) ?
C2 C1 C1 . 2 117.16(19) ?
C6 C1 C1 . 2 125.11(17) ?
C3 C2 C1 . . 121.6(3) ?
C3 C2 H2 . . 119.2 ?
C1 C2 H2 . . 119.2 ?
C4 C3 C2 . . 119.9(2) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C5 C4 C3 . . 119.4(2) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
C4 C5 C6 . . 121.6(3) ?
C4 C5 H5 . . 119.2 ?
C6 C5 H5 . . 119.2 ?
C5 C6 C1 . . 119.7(2) ?
C5 C6 C7 . . 118.4(2) ?
C1 C6 C7 . . 121.9(2) ?
O1 C7 O2 . . 121.9(2) ?
O1 C7 C6 . . 123.4(2) ?
O2 C7 C6 . . 114.5(2) ?
O3 C8 N1 . . 119.35(19) ?
O3 C8 C9 . . 125.2(2) ?
N1 C8 C9 . . 115.5(2) ?
C10 C9 C8 . . 121.1(2) ?
C10 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
C9 C10 C11 . . 121.0(2) ?
C9 C10 H10 . . 119.5 ?
C11 C10 H10 . . 119.5 ?
C12 C11 C10 . . 118.3(2) ?
C12 C11 H11 . . 120.8 ?
C10 C11 H11 . . 120.8 ?
C11 C12 N1 . . 120.2(2) ?
C11 C12 H12 . . 119.9 ?
N1 C12 H12 . . 119.9 ?
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
O1 C7 . 1.205(3) ?
O2 C7 . 1.304(3) ?
O2 H1O2 . 0.8200 ?
O3 C8 . 1.257(3) ?
N1 C12 . 1.358(3) ?
N1 C8 . 1.354(3) ?
N1 H1N1 . 0.8600 ?
C1 C2 . 1.384(3) ?
C1 C6 . 1.399(3) ?
C1 C1 2 1.495(4) ?
C2 C3 . 1.392(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.365(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.368(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.389(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.482(3) ?
C8 C9 . 1.415(3) ?
C9 C10 . 1.346(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.388(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.352(4) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 1.2(4) ?
C1 C1 C2 C3 2 . . . 179.1(3) ?
C1 C2 C3 C4 . . . . -0.4(5) ?
C2 C3 C4 C5 . . . . -0.7(5) ?
C3 C4 C5 C6 . . . . 1.0(4) ?
C4 C5 C6 C1 . . . . -0.2(4) ?
C4 C5 C6 C7 . . . . -178.0(2) ?
C2 C1 C6 C5 . . . . -0.9(3) ?
C1 C1 C6 C5 2 . . . -178.6(2) ?
C2 C1 C6 C7 . . . . 176.8(2) ?
C1 C1 C6 C7 2 . . . -0.9(4) ?
C5 C6 C7 O1 . . . . 153.8(3) ?
C1 C6 C7 O1 . . . . -24.0(4) ?
C5 C6 C7 O2 . . . . -21.0(4) ?
C1 C6 C7 O2 . . . . 161.2(2) ?
C12 N1 C8 O3 . . . . -178.0(2) ?
C12 N1 C8 C9 . . . . 2.7(3) ?
O3 C8 C9 C10 . . . . 179.2(3) ?
N1 C8 C9 C10 . . . . -1.5(4) ?
C8 C9 C10 C11 . . . . -0.6(4) ?
C9 C10 C11 C12 . . . . 1.7(4) ?
C10 C11 C12 N1 . . . . -0.6(4) ?
C8 N1 C12 C11 . . . . -1.8(4) ?
