#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/48/2014863.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_2014863
loop_
_publ_author_name
'Tsonko Kolev'
'Denitsa Yancheva'
'Boris Shivachev'
'Rosica Petrova'
'Michael Spiteller'
_publ_section_title
;
 2-(3-Benzoyl-1-pyridinio)-3,4-dioxocyclobutenolate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o213
_journal_page_last               o215
_journal_paper_doi               10.1107/S0108270105003069
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C16 H9 N O4'
_chemical_formula_moiety         'C16 H9 N O4'
_chemical_formula_sum            'C16 H9 N O4'
_chemical_formula_weight         279.24
_chemical_melting_point          418
_chemical_name_common            '3-benzoylpyridinium betaine of squaric acid'
_chemical_name_systematic
;
2-(3-Benzoyl-1-pyridinio)-3,4-dioxocyclobutenolate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 103.903(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9319(11)
_cell_length_b                   13.6577(14)
_cell_length_c                   12.0890(12)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      19.60
_cell_measurement_theta_min      18.39
_cell_volume                     1271.3(3)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'non-profiled ω/2θ'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0929
_diffrn_reflns_av_sigmaI/netI    0.0889
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6407
_diffrn_reflns_theta_full        27.98
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.342
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1423
_refine_ls_R_factor_gt           0.0673
_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)+(0.1235P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1832
_refine_ls_wR_factor_ref         0.2363
_reflns_number_gt                1558
_reflns_number_total             3063
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob1218.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

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_sg_symbol_H-M      'P 21/n'
_cod_database_code               2014863
_cod_database_fobs_code          2014863
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 -0.1537(4) 0.2684(2) 0.7565(3) 0.0501(8) Uani d . 1 . . C
H1 -0.2144 0.2439 0.6865 0.060 Uiso calc R 1 . . H
C2 -0.0726(4) 0.3590(2) 0.7617(2) 0.0450(7) Uani d . 1 . . C
C3 0.0186(4) 0.3943(2) 0.8674(3) 0.0557(9) Uani d . 1 . . C
H3 0.0744 0.4545 0.8722 0.067 Uiso calc R 1 . . H
C4 0.0264(5) 0.3403(3) 0.9648(3) 0.0645(10) Uani d . 1 . . C
H4 0.0866 0.3645 1.0351 0.077 Uiso calc R 1 . . H
C5 -0.0545(5) 0.2507(3) 0.9586(3) 0.0644(10) Uani d . 1 . . C
H5 -0.0484 0.2144 1.0244 0.077 Uiso calc R 1 . . H
C6 -0.1450(5) 0.2147(3) 0.8541(3) 0.0597(9) Uani d . 1 . . C
H6 -0.1999 0.1541 0.8498 0.072 Uiso calc R 1 . . H
C7 -0.0922(4) 0.4227(2) 0.6605(2) 0.0498(8) Uani d . 1 . . C
C8 -0.1268(4) 0.3790(2) 0.5435(2) 0.0468(7) Uani d . 1 . . C
C9 -0.2293(4) 0.4294(2) 0.4507(3) 0.0575(9) Uani d . 1 . . C
H9 -0.2784 0.4892 0.4625 0.069 Uiso calc R 1 . . H
C10 -0.2581(5) 0.3926(3) 0.3436(3) 0.0642(10) Uani d . 1 . . C
H10 -0.3294 0.4260 0.2830 0.077 Uiso calc R 1 . . H
C11 -0.1815(4) 0.3056(3) 0.3247(3) 0.0571(9) Uani d . 1 . . C
H11 -0.1985 0.2805 0.2513 0.069 Uiso calc R 1 . . H
C12 -0.0538(4) 0.2919(2) 0.5224(2) 0.0457(7) Uani d . 1 . . C
H12 0.0149 0.2567 0.5824 0.055 Uiso calc R 1 . . H
C13 -0.0073(4) 0.1671(2) 0.3952(2) 0.0482(8) Uani d . 1 . . C
C14 -0.0232(5) 0.1106(2) 0.2940(3) 0.0552(9) Uani d . 1 . . C
C15 0.0966(4) 0.0350(3) 0.3663(3) 0.0523(8) Uani d . 1 . . C
C16 0.1077(4) 0.1018(2) 0.4696(2) 0.0470(7) Uani d . 1 . . C
N1 -0.0810(3) 0.25700(17) 0.41463(19) 0.0455(6) Uani d . 1 . . N
O1 -0.0839(4) 0.51134(16) 0.6689(2) 0.0685(7) Uani d . 1 . . O
O2 0.1785(3) 0.09874(17) 0.57090(18) 0.0602(7) Uani d . 1 . . O
O3 -0.1006(4) 0.11820(18) 0.19422(19) 0.0845(10) Uani d . 1 . . O
O4 0.1552(4) -0.04321(19) 0.3487(2) 0.0762(8) Uani d . 1 . . O
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
0 6 -1
-2 0 4
-3 -2 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 120.6(3)
C6 C1 H1 119.7
C2 C1 H1 119.7
C3 C2 C1 118.8(3)
C3 C2 C7 118.9(3)
C1 C2 C7 122.0(3)
C4 C3 C2 120.3(3)
C4 C3 H3 119.8
C2 C3 H3 119.8
C5 C4 C3 120.3(3)
C5 C4 H4 119.9
C3 C4 H4 119.9
C6 C5 C4 120.0(3)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C1 120.0(3)
C5 C6 H6 120.0
C1 C6 H6 120.0
O1 C7 C2 121.6(3)
O1 C7 C8 118.0(3)
C2 C7 C8 120.4(3)
C12 C8 C9 117.8(3)
C12 C8 C7 122.0(3)
C9 C8 C7 120.1(3)
C10 C9 C8 121.1(3)
C10 C9 H9 119.5
C8 C9 H9 119.5
C9 C10 C11 119.8(3)
C9 C10 H10 120.1
C11 C10 H10 120.1
N1 C11 C10 119.1(3)
N1 C11 H11 120.4
C10 C11 H11 120.4
N1 C12 C8 120.4(3)
N1 C12 H12 119.8
C8 C12 H12 119.8
N1 C13 C14 131.5(3)
N1 C13 C16 132.0(2)
C14 C13 C16 96.5(3)
N1 C13 C15 179.1(3)
O3 C14 C13 136.2(3)
O3 C14 C15 136.0(3)
C13 C14 C15 87.8(2)
O4 C15 C14 135.4(3)
O4 C15 C16 136.3(3)
C14 C15 C16 88.2(2)
O4 C15 C13 179.1(3)
O2 C16 C13 136.4(3)
O2 C16 C15 136.1(3)
C13 C16 C15 87.4(2)
C12 N1 C11 121.7(3)
C12 N1 C13 119.5(2)
C11 N1 C13 118.8(3)
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 C6 . 1.377(4) ?
C1 C2 . 1.389(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.394(4) ?
C2 C7 . 1.478(4) yes
C3 C4 . 1.379(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.374(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.385(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O1 . 1.216(4) yes
C7 C8 . 1.498(4) yes
C8 C12 . 1.374(4) ?
C8 C9 . 1.398(4) ?
C9 C10 . 1.356(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.378(5) ?
C10 H10 . 0.9300 ?
C11 N1 . 1.357(4) ?
C11 H11 . 0.9300 ?
C12 N1 . 1.355(4) ?
C12 H12 . 0.9300 ?
C13 N1 . 1.404(4) ?
C13 C14 . 1.426(4) yes
C13 C16 . 1.430(4) yes
C14 O3 . 1.220(4) yes
C14 C15 . 1.527(5) yes
C15 O4 . 1.204(4) yes
C15 C16 . 1.533(4) yes
C16 O2 . 1.219(3) yes
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
C9 H9 O3 2_455 0.93 2.59 3.225(4) 125
C10 H10 O2 4_565 0.93 2.60 3.215(3) 124
C11 H11 O3 . 0.93 2.50 3.152(5) 127
C12 H12 O2 . 0.93 2.54 3.191(4) 127
