#------------------------------------------------------------------------------
#$Date: 2022-10-12 01:42:57 +0300 (Wed, 12 Oct 2022) $
#$Revision: 278532 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/56/7245652.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7245652
loop_
_publ_author_name
'Gołdyn, Mateusz'
'Skowronek, Julia'
'Komasa, Anna'
'Bartoszak-Adamska, Elżbieta'
'Lewandowska, Aneta'
'Dega-Szafran, Zofia'
'Cofta, Grzegorz'
_publ_section_title
;
 Synthesis and structural characteristic of pyridine carboxylic acids
 adducts with squaric acid
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00760F
_journal_year                    2022
_chemical_formula_moiety         'C4 H O4, C6 H6 N O2'
_chemical_formula_sum            'C10 H7 N O6'
_chemical_formula_weight         237.17
_chemical_melting_point          552
_chemical_name_common            '4-carboxypyridinium hydrogen squarate'
_chemical_name_systematic        'isonicotinium hydrogen squarate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-09
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2021-12-14 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                82.366(4)
_cell_angle_beta                 77.224(3)
_cell_angle_gamma                78.515(4)
_cell_formula_units_Z            4
_cell_length_a                   6.5246(2)
_cell_length_b                   11.8093(6)
_cell_length_c                   12.8138(5)
_cell_measurement_reflns_used    4993
_cell_measurement_temperature    134.6(2)
_cell_measurement_theta_max      76.0350
_cell_measurement_theta_min      3.5200
_cell_volume                     939.51(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      134.6(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5384
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -94.00 -39.00   1.00    1.00    --  -41.23 125.00  60.00   55
  2  ω    -71.00 -15.00   1.00    1.00    --  -41.23 125.00-180.00   56
  3  ω     24.00  71.00   1.00    1.00    --   41.23-125.00   0.00   47
  4  ω    -39.00  26.00   1.00    1.00    --   41.23 -19.00 -30.00   65
  5  ω      0.00 121.00   1.00    1.00    --   41.23  19.00 150.00  121
  6  ω     78.00 104.00   1.00    5.00    --  112.00 -94.00-120.00   26
  7  ω     85.00 146.00   1.00    5.00    --  112.00  30.00 -30.00   61
  8  ω     42.00  69.00   1.00    5.00    --  112.00 -61.00-120.00   27
  9  ω     40.00  70.00   1.00    5.00    --  112.00 -61.00   0.00   30
 10  ω     61.00  87.00   1.00    5.00    --  112.00-111.00-180.00   26
 11  ω     90.00 158.00   1.00    5.00    --  112.00  15.00-180.00   68
 12  ω     40.00  67.00   1.00    5.00    --  112.00 -61.00 -60.00   27
 13  ω     70.00 109.00   1.00    5.00    --  112.00-111.00 -60.00   39
 14  ω     84.00 155.00   1.00    5.00    --  112.00  61.00-180.00   71
 15  ω     83.00 145.00   1.00    5.00    --  112.00  61.00  60.00   62
 16  ω     42.00  67.00   1.00    5.00    --  112.00 -61.00 -90.00   25
 17  ω    112.00 142.00   1.00    5.00    --  112.00  77.00  30.00   30
 18  ω     46.00  71.00   1.00    5.00    --  112.00 -61.00-150.00   25
 19  ω    105.00 131.00   1.00    5.00    --  112.00 179.00-150.00   26
 20  ω     75.00 109.00   1.00    5.00    --  112.00-111.00 -30.00   34
 21  ω     43.00 109.00   1.00    5.00    --  112.00-111.00-150.00   66
 22  ω     59.00  86.00   1.00    5.00    --  112.00  15.00-180.00   27
 23  ω     73.00 109.00   1.00    5.00    --  112.00-111.00  60.00   36
 24  ω     80.00 105.00   1.00    5.00    --  112.00 -94.00  60.00   25
 25  ω     50.00  94.00   1.00    5.00    --  112.00 179.00-150.00   44
 26  ω     84.00 158.00   1.00    5.00    --  112.00  30.00 -90.00   74
 27  ω     41.00  68.00   1.00    5.00    --  112.00 -61.00  60.00   27
 28  ω     79.00 105.00   1.00    5.00    --  112.00-111.00 150.00   26
 29  ω    112.00 157.00   1.00    5.00    --  112.00  30.00  30.00   45
 30  ω     41.00  67.00   1.00    5.00    --  112.00 -61.00-180.00   26
 31  ω     40.00  68.00   1.00    5.00    --  112.00 -61.00  90.00   28
 32  ω     42.00  68.00   1.00    5.00    --  112.00 -61.00 120.00   26
 33  ω     85.00 127.00   1.00    5.00    --  112.00 179.00 -30.00   42
 34  ω     68.00  97.00   1.00    5.00    --  112.00 -77.00  30.00   29
 35  ω     95.00 120.00   1.00    5.00    --  112.00  45.00   0.00   25
 36  ω     36.00 102.00   1.00    5.00    --  112.00-111.00  30.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1953204000
_diffrn_orient_matrix_UB_12      0.0267598000
_diffrn_orient_matrix_UB_13      -0.0539611000
_diffrn_orient_matrix_UB_21      -0.0298805000
_diffrn_orient_matrix_UB_22      0.1290281000
_diffrn_orient_matrix_UB_23      0.0185126000
_diffrn_orient_matrix_UB_31      0.1464217000
_diffrn_orient_matrix_UB_32      0.0225963000
_diffrn_orient_matrix_UB_33      -0.1098896000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8341
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.446
_diffrn_reflns_theta_min         3.552
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.235
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.102a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile-water'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         3877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0827P)²+0.1046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3378
_reflns_number_total             3877
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00760f2.cif
_cod_data_source_block           mg-red-sqa-izonica
_cod_database_code               7245652
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C10H7N1O6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.748
_reflns_odcompleteness_completeness 99.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.236
_oxdiff_exptl_absorpt_empirical_full_min 0.799
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O12A O 0.50080(16) 0.49573(8) 0.22250(7) 0.0254(2) Uani 1 1 d . . . . .
O13A O 0.75344(16) 0.51398(9) -0.02130(8) 0.0264(2) Uani 1 1 d . . . . .
O12 O 0.14508(17) 0.25034(8) 0.56346(8) 0.0269(2) Uani 1 1 d . . . . .
O11A O 0.56724(16) 0.75747(8) 0.24756(7) 0.0266(2) Uani 1 1 d . . . . .
O11 O 0.19399(16) -0.03058(8) 0.55958(7) 0.0261(2) Uani 1 1 d . . . . .
O13 O -0.09879(16) 0.23123(9) 0.80919(8) 0.0272(2) Uani 1 1 d . . . . .
O1A O 0.33994(17) 0.54434(9) 0.41498(8) 0.0286(2) Uani 1 1 d . . . . .
O2 O 0.37922(16) 0.00343(9) 0.36807(7) 0.0272(2) Uani 1 1 d . . . . .
O2A O 0.36576(17) 0.72606(9) 0.43785(8) 0.0286(2) Uani 1 1 d . . . . .
O14A O 0.81628(17) 0.77561(9) -0.00312(8) 0.0295(2) Uani 1 1 d . . . . .
O1 O 0.34632(17) 0.19518(9) 0.37750(8) 0.0310(2) Uani 1 1 d . . . . .
O14 O -0.07099(17) -0.04551(9) 0.80638(8) 0.0282(2) Uani 1 1 d . . . . .
N1A N -0.03926(17) 0.58374(10) 0.78747(9) 0.0222(2) Uani 1 1 d . . . . .
N1 N 0.73598(18) 0.15231(10) 0.00711(9) 0.0226(2) Uani 1 1 d . . . . .
C4A C 0.1850(2) 0.61486(11) 0.58327(10) 0.0211(3) Uani 1 1 d . . . . .
C4 C 0.5230(2) 0.11947(12) 0.21390(10) 0.0210(3) Uani 1 1 d . . . . .
C12A C 0.5888(2) 0.57815(11) 0.15986(10) 0.0209(3) Uani 1 1 d . . . . .
C11 C 0.1092(2) 0.04124(11) 0.62687(10) 0.0212(3) Uani 1 1 d . . . . .
C3 C 0.5910(2) 0.02609(12) 0.15136(10) 0.0222(3) Uani 1 1 d . . . . .
C5 C 0.5637(2) 0.22915(12) 0.17061(11) 0.0224(3) Uani 1 1 d . . . . .
C3A C 0.1351(2) 0.70519(12) 0.64880(11) 0.0221(3) Uani 1 1 d . . . . .
C13A C 0.7010(2) 0.58151(11) 0.05058(10) 0.0210(3) Uani 1 1 d . . . . .
C11A C 0.6153(2) 0.69224(11) 0.17319(10) 0.0214(3) Uani 1 1 d . . . . .
C12 C 0.0877(2) 0.16333(11) 0.63118(10) 0.0220(3) Uani 1 1 d . . . . .
C5A C 0.1217(2) 0.50840(12) 0.62183(11) 0.0223(3) Uani 1 1 d . . . . .
C2A C 0.0197(2) 0.68730(12) 0.75256(11) 0.0228(3) Uani 1 1 d . . . . .
C14A C 0.7324(2) 0.70276(12) 0.05828(10) 0.0223(3) Uani 1 1 d . . . . .
C6A C 0.0078(2) 0.49519(11) 0.72585(10) 0.0230(3) Uani 1 1 d . . . . .
C7 C 0.4057(2) 0.10738(12) 0.32929(10) 0.0229(3) Uani 1 1 d . . . . .
C2 C 0.6993(2) 0.04523(12) 0.04633(11) 0.0227(3) Uani 1 1 d . . . . .
C14 C -0.0110(2) 0.03145(11) 0.74095(10) 0.0220(3) Uani 1 1 d . . . . .
C7A C 0.3067(2) 0.62662(12) 0.46933(10) 0.0220(3) Uani 1 1 d . . . . .
C6 C 0.6735(2) 0.24366(12) 0.06592(11) 0.0230(3) Uani 1 1 d . . . . .
C13 C -0.0240(2) 0.15991(11) 0.74084(10) 0.0220(3) Uani 1 1 d . . . . .
H2AA H -0.022(3) 0.7462(17) 0.8006(16) 0.027(4) Uiso 1 1 d . . . . .
H3A H 0.177(3) 0.7765(17) 0.6209(15) 0.027(4) Uiso 1 1 d . . . . .
H2B H 0.754(3) -0.0158(19) -0.0053(17) 0.035(5) Uiso 1 1 d . . . . .
H3 H 0.571(3) -0.0491(18) 0.1804(16) 0.027(4) Uiso 1 1 d . . . . .
H6A H -0.038(3) 0.4236(18) 0.7597(16) 0.031(5) Uiso 1 1 d . . . . .
H5 H 0.516(3) 0.2967(18) 0.2138(16) 0.032(5) Uiso 1 1 d . . . . .
H5A H 0.161(3) 0.4458(19) 0.5747(17) 0.034(5) Uiso 1 1 d . . . . .
H6 H 0.706(3) 0.319(2) 0.0313(17) 0.036(5) Uiso 1 1 d . . . . .
H1 H 0.814(4) 0.171(2) -0.071(2) 0.058(7) Uiso 1 1 d . . . . .
H1A H -0.126(4) 0.568(2) 0.861(2) 0.051(6) Uiso 1 1 d . . . . .
H2A H 0.455(4) 0.733(2) 0.361(2) 0.058(7) Uiso 1 1 d . . . . .
H12A H 0.441(4) 0.522(2) 0.292(2) 0.054(6) Uiso 1 1 d . . . . .
H12 H 0.226(4) 0.220(3) 0.495(2) 0.070(8) Uiso 1 1 d . . . . .
H2 H 0.301(4) -0.003(2) 0.450(2) 0.059(7) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12A O12A H12A 109.4(16) . . ?
C12 O12 H12 108.8(17) . . ?
C11 O11 H2 125.6(11) . . ?
C7 O2 H2 114.1(15) . . ?
C7A O2A H2A 115.4(15) . . ?
C2A N1A H1A 122.3(15) . . ?
C6A N1A C2A 122.81(11) . . ?
C6A N1A H1A 114.8(15) . . ?
C2 N1 H1 122.3(15) . . ?
C6 N1 C2 122.74(11) . . ?
C6 N1 H1 114.9(15) . . ?
C3A C4A C5A 120.41(12) . . ?
C3A C4A C7A 122.32(12) . . ?
C5A C4A C7A 117.27(12) . . ?
C3 C4 C7 122.60(12) . . ?
C5 C4 C3 119.97(12) . . ?
C5 C4 C7 117.42(12) . . ?
O12A C12A C13A 131.10(12) . . ?
O12A C12A C11A 135.03(12) . . ?
C11A C12A C13A 93.85(11) . . ?
O11 C11 C12 136.86(12) . . ?
O11 C11 C14 133.83(12) . . ?
C12 C11 C14 89.29(10) . . ?
C4 C3 H3 121.0(12) . . ?
C2 C3 C4 118.57(12) . . ?
C2 C3 H3 120.3(12) . . ?
C4 C5 H5 121.1(12) . . ?
C6 C5 C4 119.30(12) . . ?
C6 C5 H5 119.6(12) . . ?
C4A C3A H3A 119.0(12) . . ?
C2A C3A C4A 118.50(12) . . ?
C2A C3A H3A 122.4(12) . . ?
O13A C13A C12A 136.20(13) . . ?
O13A C13A C14A 134.71(12) . . ?
C12A C13A C14A 89.09(10) . . ?
O11A C11A C12A 136.71(12) . . ?
O11A C11A C14A 134.11(12) . . ?
C12A C11A C14A 89.17(10) . . ?
O12 C12 C11 135.34(12) . . ?
O12 C12 C13 131.01(12) . . ?
C11 C12 C13 93.64(11) . . ?
C4A C5A H5A 118.9(12) . . ?
C6A C5A C4A 118.69(12) . . ?
C6A C5A H5A 122.4(12) . . ?
N1A C2A C3A 119.75(12) . . ?
N1A C2A H2AA 117.7(12) . . ?
C3A C2A H2AA 122.5(12) . . ?
O14A C14A C13A 135.11(12) . . ?
O14A C14A C11A 137.01(13) . . ?
C11A C14A C13A 87.88(10) . . ?
N1A C6A C5A 119.85(12) . . ?
N1A C6A H6A 116.1(12) . . ?
C5A C6A H6A 124.0(12) . . ?
O2 C7 C4 115.62(11) . . ?
O1 C7 O2 126.22(12) . . ?
O1 C7 C4 118.16(12) . . ?
N1 C2 C3 119.89(12) . . ?
N1 C2 H2B 115.2(12) . . ?
C3 C2 H2B 124.9(12) . . ?
O14 C14 C11 136.75(12) . . ?
O14 C14 C13 135.24(12) . . ?
C11 C14 C13 88.01(10) . . ?
O1A C7A O2A 126.10(12) . . ?
O1A C7A C4A 118.85(12) . . ?
O2A C7A C4A 115.05(11) . . ?
N1 C6 C5 119.52(12) . . ?
N1 C6 H6 117.9(12) . . ?
C5 C6 H6 122.6(12) . . ?
O13 C13 C12 136.36(12) . . ?
O13 C13 C14 134.59(12) . . ?
C12 C13 C14 89.03(10) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O12A C12A 1.3161(16) . ?
O12A H12A 0.95(3) . ?
O13A C13A 1.2443(17) . ?
O12 C12 1.3121(16) . ?
O12 H12 0.99(3) . ?
O11A C11A 1.2517(17) . ?
O11 C11 1.2510(17) . ?
O11 H2 1.45(3) . ?
O13 C13 1.2481(17) . ?
O1A C7A 1.2269(18) . ?
O2 C7 1.2915(17) . ?
O2 H2 1.06(3) . ?
O2A C7A 1.2945(17) . ?
O2A H2A 1.03(3) . ?
O14A C14A 1.2149(17) . ?
O1 C7 1.2293(18) . ?
O14 C14 1.2149(17) . ?
N1A C2A 1.3453(18) . ?
N1A C6A 1.3400(18) . ?
N1A H1A 1.00(2) . ?
N1 C2 1.3444(18) . ?
N1 C6 1.3427(18) . ?
N1 H1 1.04(3) . ?
C4A C3A 1.3885(18) . ?
C4A C5A 1.3954(18) . ?
C4A C7A 1.5029(16) . ?
C4 C3 1.3921(18) . ?
C4 C5 1.3919(19) . ?
C4 C7 1.5096(17) . ?
C12A C13A 1.4290(17) . ?
C12A C11A 1.4287(18) . ?
C11 C12 1.4279(18) . ?
C11 C14 1.4999(16) . ?
C3 C2 1.3870(18) . ?
C3 H3 0.94(2) . ?
C5 C6 1.3800(18) . ?
C5 H5 0.99(2) . ?
C3A C2A 1.3877(18) . ?
C3A H3A 0.94(2) . ?
C13A C14A 1.5050(18) . ?
C11A C14A 1.5031(16) . ?
C12 C13 1.4322(17) . ?
C5A C6A 1.3806(18) . ?
C5A H5A 0.98(2) . ?
C2A H2AA 0.95(2) . ?
C6A H6A 0.97(2) . ?
C2 H2B 1.00(2) . ?
C14 C13 1.5023(18) . ?
C6 H6 0.98(2) . ?
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
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O13 1.04(3) 1.63(3) 2.6506(14) 166(2) 1_654 yes
N1A H1A O13A 1.00(2) 1.65(2) 2.6371(14) 168(2) 1_456 yes
O2A H2A O11A 1.03(3) 1.49(3) 2.5193(13) 173(2) . yes
O12A H12A O1A 0.95(3) 1.61(3) 2.5505(13) 171(2) . yes
O12 H12 O1 0.99(3) 1.57(3) 2.5523(13) 170(3) . yes
O2 H2 O11 1.06(3) 1.45(3) 2.5028(13) 171(2) . yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12A C12A C13A O13A 0.3(3) . . . . ?
O12A C12A C13A C14A -179.20(15) . . . . ?
O12A C12A C11A O11A 0.2(3) . . . . ?
O12A C12A C11A C14A 179.10(16) . . . . ?
O13A C13A C14A O14A 1.2(3) . . . . ?
O13A C13A C14A C11A -178.86(16) . . . . ?
O12 C12 C13 O13 -2.0(3) . . . . ?
O12 C12 C13 C14 178.95(15) . . . . ?
O11A C11A C14A O14A -1.8(3) . . . . ?
O11A C11A C14A C13A 178.28(16) . . . . ?
O11 C11 C12 O12 2.3(3) . . . . ?
O11 C11 C12 C13 -177.58(17) . . . . ?
O11 C11 C14 O14 -1.6(3) . . . . ?
O11 C11 C14 C13 177.70(16) . . . . ?
O14 C14 C13 O13 1.4(3) . . . . ?
O14 C14 C13 C12 -179.60(17) . . . . ?
C4A C3A C2A N1A 0.6(2) . . . . ?
C4A C5A C6A N1A -0.1(2) . . . . ?
C4 C3 C2 N1 -0.1(2) . . . . ?
C4 C5 C6 N1 1.1(2) . . . . ?
C12A C13A C14A O14A -179.19(17) . . . . ?
C12A C13A C14A C11A 0.70(10) . . . . ?
C12A C11A C14A O14A 179.19(18) . . . . ?
C12A C11A C14A C13A -0.70(10) . . . . ?
C11 C12 C13 O13 177.87(17) . . . . ?
C11 C12 C13 C14 -1.14(10) . . . . ?
C11 C14 C13 O13 -177.96(16) . . . . ?
C11 C14 C13 C12 1.09(10) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C3 C4 C7 O2 2.54(19) . . . . ?
C3 C4 C7 O1 -177.95(12) . . . . ?
C5 C4 C3 C2 0.2(2) . . . . ?
C5 C4 C7 O2 -177.06(12) . . . . ?
C5 C4 C7 O1 2.44(19) . . . . ?
C3A C4A C5A C6A 0.4(2) . . . . ?
C3A C4A C7A O1A -177.92(13) . . . . ?
C3A C4A C7A O2A 1.60(19) . . . . ?
C13A C12A C11A O11A -178.20(17) . . . . ?
C13A C12A C11A C14A 0.74(10) . . . . ?
C11A C12A C13A O13A 178.81(17) . . . . ?
C11A C12A C13A C14A -0.73(10) . . . . ?
C12 C11 C14 O14 179.61(17) . . . . ?
C12 C11 C14 C13 -1.09(10) . . . . ?
C5A C4A C3A C2A -0.6(2) . . . . ?
C5A C4A C7A O1A 1.81(19) . . . . ?
C5A C4A C7A O2A -178.67(12) . . . . ?
C2A N1A C6A C5A 0.1(2) . . . . ?
C6A N1A C2A C3A -0.3(2) . . . . ?
C7 C4 C3 C2 -179.44(11) . . . . ?
C7 C4 C5 C6 178.99(12) . . . . ?
C2 N1 C6 C5 -1.1(2) . . . . ?
C14 C11 C12 O12 -178.95(16) . . . . ?
C14 C11 C12 C13 1.14(10) . . . . ?
C7A C4A C3A C2A 179.13(11) . . . . ?
C7A C4A C5A C6A -179.36(11) . . . . ?
C6 N1 C2 C3 0.6(2) . . . . ?
