# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mg_nica-sqa
_database_code_depnum_ccdc_archive 'CCDC 2128710'
loop_
_audit_author_name
_audit_author_address
'Mateusz Goldyn'
;Adam Mickiewicz University, Faculty of Chemistry
Poland
;

_audit_update_record             
;
2021-12-14 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;
# publcif _publ_body_element loop end
# start Validation Reply Form
_vrf_PLAT934_ALERT_3_B           
;
PROBLEM: PLAT772_ALERT_2_B Suspect O-H Bond in CIF: O11A     --H2A       ..     
  1.44 Ang.  

RESPONSE: The distance shown is the length of the  H2A ... O11A hydrogen bond as
 reported in the table with hydrogen-bond geometry.
;
# end Validation Reply Form
_audit_creation_date             2021-06-10
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
'3-carboxypyridinium hydrogen squarate hemihydrate'
_chemical_name_systematic        'nicotinium hydrogen squarate hemihydrate'
_chemical_formula_moiety         '2(C4 H O4), 2(C6 H6 N O2), H2 O'
_chemical_formula_sum            'C20 H16 N2 O13'
_chemical_formula_weight         492.35
_chemical_melting_point          547
_chemical_oxdiff_formula         'C20 H16 N2 O13'
_chemical_oxdiff_usercomment     '0.19 x 0.20 x 0.38 block, 100K'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7193(11)
_cell_length_b                   9.8781(16)
_cell_length_c                   11.6443(16)
_cell_angle_alpha                68.313(14)
_cell_angle_beta                 78.335(11)
_cell_angle_gamma                74.819(12)
_cell_volume                     995.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2382
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.1950
_cell_measurement_theta_min      3.3900
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_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    1.642
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7416
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.562
_diffrn_reflns_theta_min         3.058
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00   4.00   1.00   16.50    --  -17.27 -57.00 -60.00   90
  2  ω    -39.00   4.00   1.00   16.50    --  -17.27 -77.00 120.00   43
  3  ω    -38.00  48.00   1.00   16.50    --  -17.27  57.00-150.00   86
  4  ω    -10.00  16.00   1.00   16.50    --  -17.27 -99.00 -30.00   26
  5  ω    -22.00   9.00   1.00   16.50    --  -17.27 -77.00-150.00   31
  6  ω    -39.00  52.00   1.00   16.50    --  -17.27  57.00  90.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0403986000
_diffrn_orient_matrix_UB_12      -0.0519763000
_diffrn_orient_matrix_UB_13      0.0481770000
_diffrn_orient_matrix_UB_21      0.0632757000
_diffrn_orient_matrix_UB_22      0.0016818000
_diffrn_orient_matrix_UB_23      -0.0429100000
_diffrn_orient_matrix_UB_31      0.0127374000
_diffrn_orient_matrix_UB_32      0.0594198000
_diffrn_orient_matrix_UB_33      0.0139737000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3247
_reflns_number_total             4246
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_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)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²+0.0766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1098
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.24757(14) 0.56641(12) 0.56006(12) 0.0178(3) Uani 1 1 d . . . . .
O13A O -0.00740(13) 0.52115(12) 0.78121(11) 0.0179(3) Uani 1 1 d . . . . .
O2A O 0.47405(13) 0.87111(12) 0.43163(12) 0.0183(3) Uani 1 1 d . . . . .
O14 O -0.34781(13) 0.05618(12) 0.86042(11) 0.0188(3) Uani 1 1 d . . . . .
O12 O -0.00893(13) 0.34367(12) 0.66729(11) 0.0176(3) Uani 1 1 d . . . . .
O1A O 0.45111(13) 0.66941(12) 0.39660(11) 0.0191(3) Uani 1 1 d . . . . .
O13 O -0.10977(13) 0.09049(12) 0.61524(11) 0.0178(3) Uani 1 1 d . . . . .
O11A O 0.29240(13) 0.85289(12) 0.61549(11) 0.0179(3) Uani 1 1 d . . . . .
O14A O 0.02886(14) 0.80752(13) 0.83888(12) 0.0227(3) Uani 1 1 d . . . . .
O11 O -0.24654(14) 0.31566(13) 0.91264(11) 0.0214(3) Uani 1 1 d . . . . .
O2 O -0.45809(14) 0.25369(13) 1.07985(12) 0.0213(3) Uani 1 1 d . . . . .
O1 O -0.42721(13) 0.43288(12) 1.14181(11) 0.0194(3) Uani 1 1 d . . . . .
O21 O 0.80681(17) 0.55180(15) -0.01157(14) 0.0270(3) Uani 1 1 d . . . . .
N1 N -0.77617(16) 0.14138(15) 1.35700(13) 0.0146(3) Uani 1 1 d . . . . .
N1A N 0.76362(16) 0.75052(15) 0.09528(14) 0.0167(3) Uani 1 1 d . . . . .
C2 C -0.67232(18) 0.18012(17) 1.26402(16) 0.0140(4) Uani 1 1 d . . . . .
C4A C 0.69724(19) 0.92048(18) 0.24350(16) 0.0155(4) Uani 1 1 d . . . . .
C13A C 0.07377(18) 0.61266(17) 0.73719(16) 0.0141(4) Uani 1 1 d . . . . .
C12A C 0.18790(18) 0.63788(17) 0.63890(16) 0.0141(4) Uani 1 1 d . . . . .
C11 C -0.20989(18) 0.25149(17) 0.83366(16) 0.0146(4) Uani 1 1 d . . . . .
C3A C 0.62248(18) 0.80944(17) 0.26644(15) 0.0150(4) Uani 1 1 d . . . . .
C14 C -0.25738(18) 0.13222(17) 0.81050(16) 0.0144(4) Uani 1 1 d . . . . .
C12 C -0.10638(18) 0.26209(17) 0.72583(16) 0.0137(4) Uani 1 1 d . . . . .
C2A C 0.65747(19) 0.72565(18) 0.18829(16) 0.0157(4) Uani 1 1 d . . . . .
C7 C -0.48863(19) 0.33505(17) 1.15225(16) 0.0150(4) Uani 1 1 d . . . . .
C5 C -0.76559(19) 0.32856(18) 1.43243(16) 0.0157(4) Uani 1 1 d . . . . .
C7A C 0.50676(19) 0.77735(17) 0.37194(16) 0.0160(4) Uani 1 1 d . . . . .
C14A C 0.08961(19) 0.74344(18) 0.76544(16) 0.0153(4) Uani 1 1 d . . . . .
C13 C -0.14735(18) 0.14877(17) 0.69841(16) 0.0141(4) Uani 1 1 d . . . . .
C4 C -0.65662(19) 0.37004(18) 1.33833(16) 0.0153(4) Uani 1 1 d . . . . .
C3 C -0.60837(18) 0.29483(17) 1.25303(15) 0.0145(4) Uani 1 1 d . . . . .
C6 C -0.82409(19) 0.21167(18) 1.44103(16) 0.0149(4) Uani 1 1 d . . . . .
C6A C 0.8385(2) 0.85665(19) 0.07267(17) 0.0183(4) Uani 1 1 d . . . . .
C11A C 0.20926(18) 0.76276(17) 0.66154(16) 0.0145(4) Uani 1 1 d . . . . .
C5A C 0.8057(2) 0.94441(19) 0.14599(17) 0.0191(4) Uani 1 1 d . . . . .
H2B H -0.6457(19) 0.1297(18) 1.2082(16) 0.012(4) Uiso 1 1 d . . . . .
H6 H -0.899(2) 0.1721(19) 1.5045(17) 0.018(5) Uiso 1 1 d . . . . .
H5A H 0.860(2) 1.0201(19) 0.1311(17) 0.019(5) Uiso 1 1 d . . . . .
H4A H 0.676(2) 0.9752(19) 0.2948(17) 0.017(5) Uiso 1 1 d . . . . .
H4 H -0.615(2) 0.4500(19) 1.3311(17) 0.022(5) Uiso 1 1 d . . . . .
H2AA H 0.6129(19) 0.6500(19) 0.1990(16) 0.016(5) Uiso 1 1 d . . . . .
H5 H -0.803(2) 0.3758(19) 1.4949(17) 0.019(5) Uiso 1 1 d . . . . .
H6A H 0.912(2) 0.8612(19) 0.0024(18) 0.024(5) Uiso 1 1 d . . . . .
H1 H -0.814(2) 0.058(2) 1.365(2) 0.038(6) Uiso 1 1 d . . . . .
H12 H -0.011(2) 0.414(2) 0.713(2) 0.053(7) Uiso 1 1 d . . . . .
H1A H 0.788(2) 0.688(2) 0.044(2) 0.048(7) Uiso 1 1 d . . . . .
H2A H 0.398(3) 0.855(3) 0.508(3) 0.069(9) Uiso 1 1 d . . . . .
H2 H -0.376(3) 0.277(2) 1.014(2) 0.056(8) Uiso 1 1 d . . . . .
H21A H 0.745(3) 0.497(3) 0.021(2) 0.057(8) Uiso 1 1 d . . . . .
H21B H 0.857(3) 0.533(3) -0.076(2) 0.056(8) Uiso 1 1 d . . . . .
H12A H 0.325(3) 0.610(3) 0.505(2) 0.059(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 1.314(2) . ?
O12A H12A 0.96(3) . ?
O13A C13A 1.253(2) . ?
O2A C7A 1.2938(19) . ?
O2A H2A 1.03(3) . ?
O14 C14 1.221(2) . ?
O12 C12 1.321(2) . ?
O12 H12 1.01(2) . ?
O1A C7A 1.235(2) . ?
O13 C13 1.250(2) . ?
O11A C11A 1.258(2) . ?
O11A H2A 1.44(3) . ?
O14A C14A 1.217(2) . ?
O11 C11 1.2468(19) . ?
O2 C7 1.3112(19) . ?
O2 H2 1.00(3) . ?
O1 C7 1.2210(19) . ?
O21 H21A 0.85(3) . ?
O21 H21B 0.86(3) . ?
N1 C2 1.339(2) . ?
N1 C6 1.343(2) . ?
N1 H1 0.95(2) . ?
N1A C2A 1.335(2) . ?
N1A C6A 1.347(2) . ?
N1A H1A 0.96(2) . ?
C2 C3 1.384(2) . ?
C2 H2B 0.917(17) . ?
C4A C3A 1.387(2) . ?
C4A C5A 1.380(3) . ?
C4A H4A 0.906(18) . ?
C13A C12A 1.422(2) . ?
C13A C14A 1.497(2) . ?
C12A C11A 1.425(2) . ?
C11 C14 1.498(2) . ?
C11 C12 1.431(2) . ?
C3A C2A 1.383(2) . ?
C3A C7A 1.488(2) . ?
C14 C13 1.498(2) . ?
C12 C13 1.436(2) . ?
C2A H2AA 0.916(18) . ?
C7 C3 1.495(2) . ?
C5 C4 1.384(3) . ?
C5 C6 1.379(2) . ?
C5 H5 0.967(19) . ?
C14A C11A 1.493(2) . ?
C4 C3 1.390(2) . ?
C4 H4 0.947(18) . ?
C6 H6 0.97(2) . ?
C6A C5A 1.369(2) . ?
C6A H6A 0.97(2) . ?
C5A H5A 0.974(18) . ?

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 111.1(14) . . ?
C7A O2A H2A 118.8(14) . . ?
C12 O12 H12 109.0(13) . . ?
C11A O11A H2A 124.4(10) . . ?
C7 O2 H2 113.6(13) . . ?
H21A O21 H21B 112(2) . . ?
C2 N1 C6 122.44(15) . . ?
C2 N1 H1 118.2(13) . . ?
C6 N1 H1 119.3(13) . . ?
C2A N1A C6A 122.47(15) . . ?
C2A N1A H1A 118.0(14) . . ?
C6A N1A H1A 119.5(14) . . ?
N1 C2 C3 120.05(16) . . ?
N1 C2 H2B 118.6(11) . . ?
C3 C2 H2B 121.4(11) . . ?
C3A C4A H4A 119.1(12) . . ?
C5A C4A C3A 120.39(16) . . ?
C5A C4A H4A 120.5(12) . . ?
O13A C13A C12A 135.64(15) . . ?
O13A C13A C14A 134.99(16) . . ?
C12A C13A C14A 89.37(13) . . ?
O12A C12A C13A 130.94(15) . . ?
O12A C12A C11A 135.62(16) . . ?
C13A C12A C11A 93.44(13) . . ?
O11 C11 C14 135.28(16) . . ?
O11 C11 C12 135.42(16) . . ?
C12 C11 C14 89.29(13) . . ?
C4A C3A C7A 122.38(15) . . ?
C2A C3A C4A 118.54(16) . . ?
C2A C3A C7A 119.08(15) . . ?
O14 C14 C11 135.80(16) . . ?
O14 C14 C13 135.94(15) . . ?
C13 C14 C11 88.25(13) . . ?
O12 C12 C11 135.70(15) . . ?
O12 C12 C13 130.93(16) . . ?
C11 C12 C13 93.36(14) . . ?
N1A C2A C3A 119.73(16) . . ?
N1A C2A H2AA 117.4(12) . . ?
C3A C2A H2AA 122.8(12) . . ?
O2 C7 C3 112.73(14) . . ?
O1 C7 O2 125.14(17) . . ?
O1 C7 C3 122.13(15) . . ?
C4 C5 H5 123.9(11) . . ?
C6 C5 C4 119.37(16) . . ?
C6 C5 H5 116.8(11) . . ?
O2A C7A C3A 113.69(15) . . ?
O1A C7A O2A 125.53(17) . . ?
O1A C7A C3A 120.79(15) . . ?
O14A C14A C13A 135.84(17) . . ?
O14A C14A C11A 136.34(16) . . ?
C11A C14A C13A 87.79(13) . . ?
O13 C13 C14 135.21(15) . . ?
O13 C13 C12 135.68(17) . . ?
C12 C13 C14 89.09(13) . . ?
C5 C4 C3 119.87(16) . . ?
C5 C4 H4 120.5(12) . . ?
C3 C4 H4 119.6(12) . . ?
C2 C3 C7 120.36(15) . . ?
C2 C3 C4 118.66(17) . . ?
C4 C3 C7 120.98(15) . . ?
N1 C6 C5 119.60(17) . . ?
N1 C6 H6 114.4(10) . . ?
C5 C6 H6 126.0(10) . . ?
N1A C6A C5A 119.86(17) . . ?
N1A C6A H6A 113.0(11) . . ?
C5A C6A H6A 127.1(11) . . ?
O11A C11A C12A 136.35(16) . . ?
O11A C11A C14A 134.24(15) . . ?
C12A C11A C14A 89.40(13) . . ?
C4A C5A H5A 120.7(11) . . ?
C6A C5A C4A 118.98(17) . . ?
C6A C5A H5A 120.3(11) . . ?

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 0.95(2) 1.74(2) 2.6865(18) 177(2) 2_457 yes
O12 H12 O13A 1.01(2) 1.55(2) 2.5639(16) 178(2) . yes
N1A H1A O21 0.96(2) 1.66(2) 2.5961(19) 165(2) . yes
O2A H2A O11A 1.03(3) 1.44(3) 2.4670(17) 172(2) . yes
O2 H2 O11 1.00(3) 1.56(3) 2.5599(19) 178(2) . yes
O21 H21A O1 0.85(3) 2.03(3) 2.819(2) 154(2) 1_654 yes
O21 H21B O13A 0.86(3) 1.92(3) 2.7689(19) 168(2) 1_654 yes
O12A H12A O1A 0.96(3) 1.63(3) 2.5830(18) 170(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 C11A O11A 0.1(4) . . . . ?
O12A C12A C11A C14A -179.8(2) . . . . ?
O13A C13A C12A O12A -0.9(3) . . . . ?
O13A C13A C12A C11A 179.7(2) . . . . ?
O13A C13A C14A O14A -1.3(4) . . . . ?
O13A C13A C14A C11A -179.7(2) . . . . ?
O14 C14 C13 O13 0.6(4) . . . . ?
O14 C14 C13 C12 179.3(2) . . . . ?
O12 C12 C13 O13 -0.5(3) . . . . ?
O12 C12 C13 C14 -179.23(18) . . . . ?
O14A C14A C11A O11A 2.1(4) . . . . ?
O14A C14A C11A C12A -178.0(2) . . . . ?
O11 C11 C14 O14 -0.1(4) . . . . ?
O11 C11 C14 C13 179.0(2) . . . . ?
O11 C11 C12 O12 0.0(4) . . . . ?
O11 C11 C12 C13 -179.0(2) . . . . ?
O2 C7 C3 C2 1.4(2) . . . . ?
O2 C7 C3 C4 -179.45(15) . . . . ?
O1 C7 C3 C2 -178.00(16) . . . . ?
O1 C7 C3 C4 1.2(3) . . . . ?
N1 C2 C3 C7 177.74(14) . . . . ?
N1 C2 C3 C4 -1.5(2) . . . . ?
N1A C6A C5A C4A 1.0(3) . . . . ?
C2 N1 C6 C5 0.2(2) . . . . ?
C4A C3A C2A N1A 1.6(2) . . . . ?
C4A C3A C7A O2A 6.3(2) . . . . ?
C4A C3A C7A O1A -173.46(16) . . . . ?
C13A C12A C11A O11A 179.5(2) . . . . ?
C13A C12A C11A C14A -0.40(13) . . . . ?
C13A C14A C11A O11A -179.6(2) . . . . ?
C13A C14A C11A C12A 0.38(12) . . . . ?
C12A C13A C14A O14A 178.0(2) . . . . ?
C12A C13A C14A C11A -0.38(12) . . . . ?
C11 C14 C13 O13 -178.5(2) . . . . ?
C11 C14 C13 C12 0.17(12) . . . . ?
C11 C12 C13 O13 178.5(2) . . . . ?
C11 C12 C13 C14 -0.18(13) . . . . ?
C3A C4A C5A C6A -0.2(3) . . . . ?
C14 C11 C12 O12 179.2(2) . . . . ?
C14 C11 C12 C13 0.18(13) . . . . ?
C12 C11 C14 O14 -179.3(2) . . . . ?
C12 C11 C14 C13 -0.17(12) . . . . ?
C2A N1A C6A C5A -0.5(3) . . . . ?
C2A C3A C7A O2A -173.91(15) . . . . ?
C2A C3A C7A O1A 6.4(2) . . . . ?
C5 C4 C3 C2 0.6(2) . . . . ?
C5 C4 C3 C7 -178.61(15) . . . . ?
C7A C3A C2A N1A -178.21(15) . . . . ?
C14A C13A C12A O12A 179.84(18) . . . . ?
C14A C13A C12A C11A 0.40(13) . . . . ?
C4 C5 C6 N1 -1.0(2) . . . . ?
C6 N1 C2 C3 1.1(2) . . . . ?
C6 C5 C4 C3 0.6(2) . . . . ?
C6A N1A C2A C3A -0.8(2) . . . . ?
C5A C4A C3A C2A -1.1(3) . . . . ?
C5A C4A C3A C7A 178.73(16) . . . . ?

_olex2_date_sample_data_collection 2020-07-13
_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 1.072
_oxdiff_exptl_absorpt_empirical_full_min 0.942



_publcif_funding_html            
;
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol-water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mg-red-sqa-izonica
_database_code_depnum_ccdc_archive 'CCDC 2128712'
loop_
_audit_author_name
_audit_author_address
'Mateusz Goldyn'
;Adam Mickiewicz University, Faculty of Chemistry
Poland
;

_audit_update_record             
;
2021-12-14 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;
# publcif _publ_body_element loop end
# start Validation Reply Form
_vrf_PLAT934_ALERT_3_B           
;
PROBLEM: PLAT772_ALERT_2_B Suspect O-H Bond in CIF: O11      --H2        ..     
  1.45 Ang.  

RESPONSE: The distance shown is the length of the H2 ... O11 hydrogen bond as
reported in the table with hydrogen-bond geometry.
;
# end Validation Reply Form
_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)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            '4-carboxypyridinium hydrogen squarate'
_chemical_name_systematic        'isonicotinium hydrogen squarate'
_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_oxdiff_formula         C10H7N1O6
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5246(2)
_cell_length_b                   11.8093(6)
_cell_length_c                   12.8138(5)
_cell_angle_alpha                82.366(4)
_cell_angle_beta                 77.224(3)
_cell_angle_gamma                78.515(4)
_cell_volume                     939.51(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4993
_cell_measurement_temperature    134.6(2)
_cell_measurement_theta_max      76.0350
_cell_measurement_theta_min      3.5200
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.748
_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_absorpt_special_details   ?
_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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3378
_reflns_number_total             3877
_reflns_odcompleteness_completeness 99.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.063
_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
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?

_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            
;
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile-water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sqa-pica-1-1-jul
_database_code_depnum_ccdc_archive 'CCDC 2128711'
loop_
_audit_author_name
_audit_author_address
'Mateusz Goldyn'
;Adam Mickiewicz University, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2021-12-14 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_DIFMN02_sqa-pica-1-1-jul    
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00
RESPONSE: Relatively strong diffusion peaks were observed in h(k+0.5)l layers of the reciprocal space pointing to stacking faults in the arrangement of planar (101) layers formed from hydrogen-bonded molecules. This effect, which was not considered in our calculations, was most probably a source of relatively high residual electron density peaks in the final difference Fourier map.
;
_vrf_PLAT097_sqa-pica-1-1-jul    
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.48 eA-3
RESPONSE: Relatively strong diffusion peaks were observed in h(k+0.5)l layers of the reciprocal space pointing to stacking faults in the arrangement of planar (101) layers formed from hydrogen-bonded molecules. This effect, which was not considered in our calculations, was most probably a source of relatively high residual electron density peaks in the final difference Fourier map.
;
_vrf_PLAT098_sqa-pica-1-1-jul    
;
PROBLEM: Large Reported Min.  (Negative) Residual Density      -1.30 eA-3
RESPONSE: Relatively strong diffusion peaks were observed in h(k+0.5)l layers of the reciprocal space pointing to stacking faults in the arrangement of planar (101) layers formed from hydrogen-bonded molecules. This effect, which was not considered in our calculations, was most probably a source of relatively high residual electron density peaks in the final difference Fourier map.
;
# Added during the CSD deposition process: Tuesday 14 December 2021 10:11 PM
# end Validation Reply Form

_audit_creation_date             2021-04-27
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            '2-carboxypyridinium hydrogen squarate'
_chemical_name_systematic        'picolinium hydrogen squarate'
_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          536
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_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'

_cell_length_a                   11.2508(9)
_cell_length_b                   16.8024(9)
_cell_length_c                   11.2451(9)
_cell_angle_alpha                90
_cell_angle_beta                 115.211(10)
_cell_angle_gamma                90
_cell_volume                     1923.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6829
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      26.3210
_cell_measurement_theta_min      3.7600
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.885
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol-water'
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3938
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.418
_diffrn_reflns_theta_min         3.145
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  75.00   1.00   10.00    --   16.56-126.00 102.00   77
  2  ω    -13.00  87.00   1.00   10.00    --   16.56  77.00   0.00  100
  3  ω    -25.00  58.00   1.00   10.00    --   16.56 -99.00-180.00   83
  4  ω     -9.00  89.00   1.00   10.00    --   16.56  37.00 -30.00   98
  5  ω    -75.00   2.00   1.00   10.00    --  -17.35 126.00-179.00   77
  6  ω    -86.00   4.00   1.00   10.00    --  -17.35 -57.00  60.00   90
  7  ω    -38.00  51.00   1.00   10.00    --  -17.35  57.00 -30.00   89
  8  ω    -38.00  51.00   1.00   10.00    --  -17.35  57.00-120.00   89
  9  ω    -86.00   4.00   1.00   10.00    --  -17.35 -57.00-180.00   90
 10  ω    -56.00  90.00   1.00   10.00    --   16.56   0.00-120.00  146
 11  ω    -25.00  58.00   1.00   10.00    --   16.56 -99.00 -30.00   83
 12  ω    -25.00  58.00   1.00   10.00    --   16.56 -99.00  90.00   83
 13  ω    -56.00  90.00   1.00   10.00    --   16.56   0.00-180.00  146
 14  ω    -56.00  90.00   1.00   10.00    --   16.56   0.00-150.00  146
 15  ω    -38.00  51.00   1.00   10.00    --  -17.35  57.00-180.00   89
 16  ω    -25.00  25.00   1.00   10.00    --  -17.35 -99.00  90.00   50
 17  ω    -56.00  90.00   1.00   10.00    --   16.56   0.00 -60.00  146
 18  ω    -56.00  90.00   1.00   10.00    --   16.56   0.00 -30.00  146
 19  ω    -56.00   2.00   1.00   10.00    --   16.56   0.00   0.00   58
 20  ω    -56.00  90.00   1.00   10.00    --   16.56   0.00 -90.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0275420000
_diffrn_orient_matrix_UB_12      0.0330820000
_diffrn_orient_matrix_UB_13      0.0185728000
_diffrn_orient_matrix_UB_21      -0.0265255000
_diffrn_orient_matrix_UB_22      -0.0259091000
_diffrn_orient_matrix_UB_23      0.0324340000
_diffrn_orient_matrix_UB_31      0.0569882000
_diffrn_orient_matrix_UB_32      0.0039238000
_diffrn_orient_matrix_UB_33      0.0576070000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2780
_reflns_number_total             3938
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.481
_refine_diff_density_min         -1.302
_refine_diff_density_rms         0.188
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3938
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      1.036
_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)+(0.0207P)²+4.4459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1191
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.0903(10)
 0.9097(10)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O2 O 0.3403(3) 0.16451(16) 0.1566(3) 0.0199(7) Uani 1 1 d . . . . .
O1 O 0.4164(2) 0.05855(13) 0.0868(3) 0.0215(5) Uani 1 1 d . . . . .
O12 O 0.3267(3) -0.05354(12) 0.1755(3) 0.0226(5) Uani 1 1 d . . . . .
O11 O 0.2227(2) 0.10632(11) 0.2763(2) 0.0204(5) Uani 1 1 d . . . . .
O14 O 0.0883(2) -0.00640(13) 0.4129(3) 0.0231(5) Uani 1 1 d . . . . .
O13 O 0.1874(3) -0.16393(16) 0.3106(3) 0.0202(7) Uani 1 1 d . . . . .
N1 N 0.4469(3) 0.26716(15) 0.0532(3) 0.0135(8) Uani 1 1 d . . . . .
C2 C 0.4637(4) 0.1878(2) 0.0374(4) 0.0122(7) Uani 1 1 d . . . . .
C3 C 0.5321(4) 0.1651(2) -0.0325(4) 0.0146(8) Uani 1 1 d . . . . .
C4 C 0.5849(5) 0.2225(2) -0.0841(5) 0.0175(9) Uani 1 1 d . . . . .
C5 C 0.5666(5) 0.3024(2) -0.0672(5) 0.0173(9) Uani 1 1 d . . . . .
C6 C 0.4963(4) 0.3236(2) 0.0024(4) 0.0152(8) Uani 1 1 d . . . . .
C7 C 0.4016(3) 0.13156(17) 0.0988(3) 0.0173(7) Uani 1 1 d . . . . .
C12 C 0.2584(4) -0.0376(2) 0.2424(4) 0.0164(9) Uani 1 1 d . . . . .
C11 C 0.2157(4) 0.0301(2) 0.2850(4) 0.0135(9) Uani 1 1 d . . . . .
C14 C 0.1511(4) -0.0183(2) 0.3497(4) 0.0176(8) Uani 1 1 d . . . . .
C13 C 0.1979(3) -0.09164(18) 0.3019(4) 0.0178(7) Uani 1 1 d . . . . .
H2 H 0.282(4) 0.135(2) 0.217(4) 0.029(11) Uiso 1 1 d . . . . .
H12 H 0.369(6) 0.007(3) 0.149(6) 0.10(2) Uiso 1 1 d . . . . .
H4 H 0.630(3) 0.2041(17) -0.134(4) 0.021(8) Uiso 1 1 d . . . . .
H6 H 0.476(3) 0.3741(18) 0.019(3) 0.018(8) Uiso 1 1 d . . . . .
H3 H 0.539(4) 0.102(2) -0.046(4) 0.037(9) Uiso 1 1 d . . . . .
H5 H 0.603(4) 0.3421(19) -0.107(4) 0.032(10) Uiso 1 1 d . . . . .
H1 H 0.403(5) 0.278(3) 0.099(5) 0.090(18) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O2 C7 1.259(3) . ?
O2 H2 1.23(4) . ?
O1 C7 1.253(3) . ?
O1 H12 1.36(6) . ?
O12 C12 1.312(4) . ?
O12 H12 1.22(6) . ?
O11 C11 1.289(4) . ?
O11 H2 1.23(4) . ?
O14 C14 1.213(4) . ?
O13 C13 1.228(4) . ?
N1 C2 1.369(5) . ?
N1 C6 1.344(4) . ?
N1 H1 0.87(4) . ?
C2 C3 1.368(5) . ?
C2 C7 1.505(4) . ?
C3 C4 1.383(5) . ?
C3 H3 1.08(3) . ?
C4 C5 1.384(5) . ?
C4 H4 0.96(3) . ?
C5 C6 1.376(5) . ?
C5 H5 0.99(3) . ?
C6 H6 0.92(3) . ?
C12 C11 1.397(4) . ?
C12 C13 1.458(5) . ?
C11 C14 1.473(5) . ?
C14 C13 1.525(5) . ?

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
C7 O2 H2 130.1(17) . . ?
C7 O1 H12 118(2) . . ?
C12 O12 H12 110(3) . . ?
C11 O11 H2 119.8(17) . . ?
C2 N1 H1 115(3) . . ?
C6 N1 C2 121.9(3) . . ?
C6 N1 H1 123(3) . . ?
N1 C2 C7 115.8(3) . . ?
C3 C2 N1 119.2(4) . . ?
C3 C2 C7 125.0(4) . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 116.4(18) . . ?
C4 C3 H3 123.9(18) . . ?
C3 C4 C5 120.2(5) . . ?
C3 C4 H4 117.0(18) . . ?
C5 C4 H4 122.8(17) . . ?
C4 C5 H5 119(2) . . ?
C6 C5 C4 119.0(4) . . ?
C6 C5 H5 122(2) . . ?
N1 C6 C5 120.1(3) . . ?
N1 C6 H6 112(2) . . ?
C5 C6 H6 128(2) . . ?
O2 C7 C2 115.0(3) . . ?
O1 C7 O2 127.8(3) . . ?
O1 C7 C2 117.1(3) . . ?
O12 C12 C11 137.3(4) . . ?
O12 C12 C13 129.7(3) . . ?
C11 C12 C13 93.0(3) . . ?
O11 C11 C12 137.8(4) . . ?
O11 C11 C14 130.2(3) . . ?
C12 C11 C14 92.0(3) . . ?
O14 C14 C11 137.0(3) . . ?
O14 C14 C13 135.6(3) . . ?
C11 C14 C13 87.4(3) . . ?
O13 C13 C12 137.1(3) . . ?
O13 C13 C14 135.3(3) . . ?
C12 C13 C14 87.6(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
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O11 1.23(4) 1.23(4) 2.457(3) 179(4) . yes
O12 H12 O1 1.22(6) 1.36(6) 2.533(3) 160(5) . yes
N1 H1 O13 0.87(4) 1.97(5) 2.817(3) 162(4) 4 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
O12 C12 C11 O11 1.2(8) . . . . ?
O12 C12 C11 C14 -179.5(5) . . . . ?
O12 C12 C13 O13 -0.8(8) . . . . ?
O12 C12 C13 C14 179.5(5) . . . . ?
O11 C11 C14 O14 -0.8(8) . . . . ?
O11 C11 C14 C13 179.2(5) . . . . ?
O14 C14 C13 O13 0.5(8) . . . . ?
O14 C14 C13 C12 -179.8(5) . . . . ?
N1 C2 C3 C4 1.0(6) . . . . ?
N1 C2 C7 O2 0.6(5) . . . . ?
N1 C2 C7 O1 -179.4(3) . . . . ?
C2 N1 C6 C5 -0.4(6) . . . . ?
C2 C3 C4 C5 -1.1(8) . . . . ?
C3 C2 C7 O2 -178.4(4) . . . . ?
C3 C2 C7 O1 1.5(6) . . . . ?
C3 C4 C5 C6 0.5(9) . . . . ?
C4 C5 C6 N1 0.3(7) . . . . ?
C6 N1 C2 C3 -0.3(6) . . . . ?
C6 N1 C2 C7 -179.4(3) . . . . ?
C7 C2 C3 C4 -179.9(4) . . . . ?
C12 C11 C14 O14 179.8(5) . . . . ?
C12 C11 C14 C13 -0.3(3) . . . . ?
C11 C12 C13 O13 179.4(5) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C11 C14 C13 O13 -179.5(5) . . . . ?
C11 C14 C13 C12 0.2(3) . . . . ?
C13 C12 C11 O11 -179.1(5) . . . . ?
C13 C12 C11 C14 0.3(3) . . . . ?

_olex2_date_sample_data_collection 2019-12-22
_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 1.101
_oxdiff_exptl_absorpt_empirical_full_min 0.871
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.0903(10)
2 0.9097(10)
