# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2025

####################################################################### 
# 
# 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_016GPa
_database_code_depnum_ccdc_archive 'CCDC 2355850'
loop_
_audit_author_name
_audit_author_address
'Michalina Rusek'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-05-16 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_audit_creation_date             2024-05-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT029_016GPa              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.423 Why?  
RESPONSE: It is due to high-pressure conditions
;
_vrf_PLAT340_016GPa              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0205 Ang.  
RESPONSE: It is due to high-pressure conditions
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H5 O3, C3 H5 N2'
_chemical_formula_sum            'C10 H10 N2 O3'
_chemical_formula_weight         206.20
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2640(13)
_cell_length_b                   10.812(11)
_cell_length_c                   16.025(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1952(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1007
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       160000(2)
_cell_measurement_theta_max      25.2560
_cell_measurement_theta_min      4.6050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Data were collected at room temperature and pressure of 0.16(2) GPa
 (160000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_crystal_size_rad          0.400
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1218
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 0.423
_diffrn_reflns_Laue_measured_fraction_max 0.385
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7165
_diffrn_reflns_point_group_measured_fraction_full 0.423
_diffrn_reflns_point_group_measured_fraction_max 0.385
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.634
_diffrn_reflns_theta_min         4.625
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.423
_diffrn_measured_fraction_theta_max 0.385
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ    -35.00  19.75   0.75   35.00   0.00 -30.00   0.00    --    73
  2  φ    140.00 200.00   0.75   35.00   0.00 -30.00   0.00    --    80
  3  φ    160.00 217.00   0.75   35.00   0.00  30.00   0.00    --    76
  4  φ    -20.00  34.75   0.75   35.00   0.00  30.00   0.00    --    73
  5  ω    -24.00  24.00   0.75   35.00    --   30.00  39.46 -12.90   64
  6  ω    -24.00  24.00   0.75   35.00    --   30.00  39.46 167.10   64
  7  ω    -50.00  10.00   0.75   35.00    --  -30.00  39.46 167.10   80
  8  ω    -50.00  10.00   0.75   35.00    --  -30.00  39.46 -12.90   80
  9  ω    -64.00  -8.50   0.75   35.00    --  -30.00  81.40 -28.90   74
 10  ω    -64.00  -8.50   0.75   35.00    --  -30.00  81.40 151.10   74
 11  ω    -19.00   8.00   0.75   35.00    --   30.00  81.40 151.10   36
 12  ω    -19.00   8.00   0.75   35.00    --   30.00  81.40 -28.90   36
 13  ω    -43.00 -21.25   0.75   35.00    --   30.00 134.60 -56.90   29
 14  ω    -43.00 -21.25   0.75   35.00    --   30.00 134.60 123.10   29
 15  ω    -90.00 -36.00   0.75   35.00    --  -30.00 134.60 123.10   72
 16  ω    -90.00 -36.00   0.75   35.00    --  -30.00 134.60 -56.90   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                337
_reflns_number_total             792
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         792
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1702
_refine_ls_R_factor_gt           0.0743
_refine_ls_restrained_S_all      0.983
_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)+(0.1221P)²+0.6795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1879
_refine_ls_wR_factor_ref         0.2554
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(C7) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(C4) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq,
Uanis(N2) \\sim Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.008
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), N1(H1), N2(H2), C8(H8), C9(H9), C10(H10)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.5383(7) 0.489(2) 0.3380(4) 0.059(3) Uani 1 1 d . U . . .
C2 C 0.5715(8) 0.364(2) 0.3334(5) 0.070(3) Uani 1 1 d . U . . .
C3 C 0.6614(7) 0.3226(19) 0.2777(5) 0.095(3) Uani 1 1 d . U . . .
H3 H 0.685676 0.240498 0.275767 0.114 Uiso 1 1 calc R U . . .
C4 C 0.7106(7) 0.413(2) 0.2263(5) 0.073(3) Uani 1 1 d . U . . .
H4 H 0.768436 0.388210 0.188343 0.088 Uiso 1 1 calc R U . . .
C5 C 0.6783(8) 0.537(2) 0.2283(5) 0.084(4) Uani 1 1 d . U . . .
H5 H 0.714366 0.595173 0.193474 0.101 Uiso 1 1 calc R U . . .
C6 C 0.5916(6) 0.5711(16) 0.2834(4) 0.073(3) Uani 1 1 d . U . . .
H6 H 0.567244 0.653300 0.284445 0.088 Uiso 1 1 calc R U . . .
C7 C 0.4440(11) 0.527(3) 0.3996(7) 0.064(4) Uani 1 1 d . U . . .
O1 O 0.4233(7) 0.6378(17) 0.4054(5) 0.077(10) Uani 1 1 d . . . . .
O2 O 0.3934(4) 0.4427(12) 0.4411(3) 0.081(8) Uani 1 1 d . . . . .
O3 O 0.5247(6) 0.2715(14) 0.3833(4) 0.103(9) Uani 1 1 d . . . . .
H3A H 0.464773 0.297108 0.406601 0.155 Uiso 1 1 calc R U . . .
N1 N 0.2115(6) 0.5582(17) 0.5234(4) 0.071(3) Uani 1 1 d . U . . .
H1 H 0.271207 0.530652 0.495511 0.085 Uiso 1 1 calc R U . . .
N2 N 0.0791(6) 0.6772(16) 0.5676(4) 0.087(3) Uani 1 1 d . U . . .
H2 H 0.032286 0.739266 0.573946 0.104 Uiso 1 1 calc R U . . .
C8 C 0.1786(9) 0.681(2) 0.5216(5) 0.092(4) Uani 1 1 d . U . . .
H8 H 0.215208 0.748388 0.495876 0.111 Uiso 1 1 calc R U . . .
C9 C 0.1421(10) 0.482(2) 0.5730(5) 0.104(4) Uani 1 1 d . U . . .
H9 H 0.147327 0.397613 0.584365 0.124 Uiso 1 1 calc R U . . .
C10 C 0.0613(9) 0.572(2) 0.6006(6) 0.086(3) Uani 1 1 d . U . . .
H10 H 0.001206 0.556536 0.639031 0.104 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.054(3) 0.060(6) 0.063(3) 0.003(4) 0.002(3) -0.001(4)
C2 0.071(4) 0.069(6) 0.068(4) 0.000(4) 0.001(3) 0.000(4)
C3 0.094(4) 0.095(6) 0.095(4) 0.000(4) 0.003(3) 0.004(4)
C4 0.069(4) 0.073(6) 0.077(4) -0.001(4) 0.006(3) -0.002(4)
C5 0.083(4) 0.084(6) 0.085(4) 0.001(4) 0.005(3) -0.005(4)
C6 0.073(3) 0.072(6) 0.075(3) 0.000(4) 0.001(3) -0.001(4)
C7 0.063(5) 0.064(6) 0.066(4) -0.002(4) -0.001(3) -0.002(4)
O1 0.062(4) 0.06(4) 0.107(5) 0.003(9) -0.011(3) -0.017(7)
O2 0.064(3) 0.10(3) 0.078(3) -0.002(5) 0.005(3) -0.005(5)
O3 0.112(5) 0.09(3) 0.110(5) 0.023(6) 0.023(4) 0.007(7)
N1 0.066(3) 0.071(6) 0.076(3) -0.003(4) 0.004(2) 0.000(4)
N2 0.082(4) 0.087(6) 0.091(3) -0.002(4) 0.002(3) 0.008(4)
C8 0.089(5) 0.092(6) 0.096(4) 0.003(4) -0.002(3) -0.002(4)
C9 0.106(4) 0.103(6) 0.101(4) 0.005(4) 0.002(3) 0.001(4)
C10 0.085(4) 0.087(6) 0.087(4) 0.002(4) 0.008(3) 0.003(4)

_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
C1 C2 1.40(2) . ?
C1 C6 1.386(18) . ?
C1 C7 1.508(15) . ?
C2 C3 1.422(15) . ?
C2 O3 1.38(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.39(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.40(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.367(14) . ?
C6 H6 0.9300 . ?
C7 O1 1.23(4) . ?
C7 O2 1.26(3) . ?
O3 H3A 0.8200 . ?
N1 H1 0.8600 . ?
N1 C8 1.38(3) . ?
N1 C9 1.388(18) . ?
N2 H2 0.8600 . ?
N2 C8 1.341(11) . ?
N2 C10 1.27(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.41(2) . ?
C10 H10 0.9300 . ?

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
C2 C1 C7 119.0(19) . . ?
C6 C1 C2 118.1(10) . . ?
C6 C1 C7 123(2) . . ?
C1 C2 C3 121.8(16) . . ?
O3 C2 C1 124.3(10) . . ?
O3 C2 C3 113.9(18) . . ?
C2 C3 H3 122.1 . . ?
C4 C3 C2 115.8(17) . . ?
C4 C3 H3 122.1 . . ?
C3 C4 H4 118.0 . . ?
C3 C4 C5 124.0(11) . . ?
C5 C4 H4 118.0 . . ?
C4 C5 H5 121.4 . . ?
C6 C5 C4 117.2(15) . . ?
C6 C5 H5 121.4 . . ?
C1 C6 H6 118.5 . . ?
C5 C6 C1 123.1(17) . . ?
C5 C6 H6 118.5 . . ?
O1 C7 C1 117(3) . . ?
O1 C7 O2 125.3(11) . . ?
O2 C7 C1 118(3) . . ?
C2 O3 H3A 109.5 . . ?
C8 N1 H1 122.2 . . ?
C8 N1 C9 115.7(11) . . ?
C9 N1 H1 122.2 . . ?
C8 N2 H2 123.5 . . ?
C10 N2 H2 123.5 . . ?
C10 N2 C8 113.1(17) . . ?
N1 C8 H8 129.8 . . ?
N2 C8 N1 100.4(16) . . ?
N2 C8 H8 129.8 . . ?
N1 C9 H9 131.2 . . ?
N1 C9 C10 97.6(16) . . ?
C10 C9 H9 131.2 . . ?
N2 C10 C9 112.8(11) . . ?
N2 C10 H10 123.6 . . ?
C9 C10 H10 123.6 . . ?

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
C1 C2 C3 C4 -2.3(13) . . . . ?
C2 C1 C6 C5 -2.9(12) . . . . ?
C2 C1 C7 O1 175.3(11) . . . . ?
C2 C1 C7 O2 -4.3(14) . . . . ?
C2 C3 C4 C5 1.3(13) . . . . ?
C3 C4 C5 C6 -1.1(15) . . . . ?
C4 C5 C6 C1 2.0(13) . . . . ?
C6 C1 C2 C3 3.1(13) . . . . ?
C6 C1 C2 O3 -179.3(6) . . . . ?
C6 C1 C7 O1 -6.7(16) . . . . ?
C6 C1 C7 O2 173.7(8) . . . . ?
C7 C1 C2 C3 -178.9(8) . . . . ?
C7 C1 C2 O3 -1.2(15) . . . . ?
C7 C1 C6 C5 179.1(9) . . . . ?
O3 C2 C3 C4 179.9(7) . . . . ?
N1 C9 C10 N2 3.7(12) . . . . ?
C8 N1 C9 C10 0.9(11) . . . . ?
C8 N2 C10 C9 -7.2(15) . . . . ?
C9 N1 C8 N2 -4.6(11) . . . . ?
C10 N2 C8 N1 6.9(12) . . . . ?
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2371024'
loop_
_audit_author_name
_audit_author_address
'Andrzej Gzella'
;Poznan University of Medical Sciences
Poland
;
_audit_update_record             
;
2024-07-15 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
Imidazolium 2-hydroxybenzoate
;
_chemical_name_common            ?
_chemical_melting_point          401-403
_chemical_formula_moiety         'C7 H5 O3^-^, C3 H5 N2^+^'
_chemical_formula_sum            'C10 H10 N2 O3'
_chemical_formula_weight         206.20

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.0988(6)
_cell_length_b                   10.9361(5)
_cell_length_c                   16.4701(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1999.10(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    4932
_cell_measurement_theta_min      3.90
_cell_measurement_theta_max      28.07


_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.62629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      240.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3991
_diffrn_reflns_number            16879
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.893
_diffrn_reflns_theta_max         29.670
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2584
_reflns_number_gt                1913
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
; 
WINGX (Farrugia, 2012), OLEX2 v1.2-alpha (Dolomanov et al., 2009), 
PLATON (Spek, 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+0.8008P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0075(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2584
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1A N 0.21062(13) 0.55602(14) 0.52323(9) 0.0497(4) Uani 1 1 d . . . . .
H1A H 0.274(3) 0.526(2) 0.4938(15) 0.093(8) Uiso 1 1 d . . . . .
N2A N 0.07813(14) 0.68097(15) 0.56663(10) 0.0532(4) Uani 1 1 d . . . . .
H2A H 0.031(2) 0.750(2) 0.5760(16) 0.098(9) Uiso 1 1 d . . . . .
C1A C 0.17360(16) 0.66962(16) 0.51955(11) 0.0503(4) Uani 1 1 d . . . . .
H1AA H 0.209018 0.732306 0.488645 0.060 Uiso 1 1 calc R U . . .
C2A C 0.0557(2) 0.5715(2) 0.60047(13) 0.0638(5) Uani 1 1 d . . . . .
H2AA H -0.007113 0.553548 0.636879 0.077 Uiso 1 1 calc R U . . .
C3A C 0.1371(2) 0.49370(18) 0.57367(12) 0.0605(5) Uani 1 1 d . . . . .
H3AA H 0.142831 0.410382 0.587153 0.073 Uiso 1 1 calc R U . . .
C1B C 0.53812(13) 0.48494(14) 0.34027(9) 0.0372(3) Uani 1 1 d . . . . .
C2B C 0.57324(15) 0.36240(16) 0.33568(10) 0.0470(4) Uani 1 1 d . . . . .
C3B C 0.66105(18) 0.32620(19) 0.28082(12) 0.0604(5) Uani 1 1 d . . . . .
H3B H 0.684757 0.243769 0.278364 0.072 Uiso 1 1 calc R U . . .
C4B C 0.71315(17) 0.4099(2) 0.23038(12) 0.0628(5) Uani 1 1 d . . . . .
H4B H 0.773320 0.384776 0.193833 0.075 Uiso 1 1 calc R U . . .
C5B C 0.67845(18) 0.53086(19) 0.23247(11) 0.0588(5) Uani 1 1 d . . . . .
H5B H 0.713775 0.587803 0.196957 0.071 Uiso 1 1 calc R U . . .
C6B C 0.59148(16) 0.56772(16) 0.28706(10) 0.0477(4) Uani 1 1 d . . . . .
H6B H 0.567822 0.650230 0.288371 0.057 Uiso 1 1 calc R U . . .
C7B C 0.44465(13) 0.52556(14) 0.39973(9) 0.0385(3) Uani 1 1 d . . . . .
O8B O 0.42047(10) 0.63612(10) 0.40738(8) 0.0494(3) Uani 1 1 d . . . . .
O9B O 0.39096(10) 0.44265(10) 0.44055(7) 0.0464(3) Uani 1 1 d . . . . .
O10B O 0.52491(15) 0.27630(12) 0.38446(10) 0.0711(5) Uani 1 1 d . . . . .
H10B H 0.463(2) 0.325(2) 0.4153(16) 0.095(8) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1A 0.0407(7) 0.0591(9) 0.0494(8) -0.0043(7) 0.0002(6) 0.0117(6)
N2A 0.0471(8) 0.0526(9) 0.0600(9) -0.0127(7) -0.0047(7) 0.0144(7)
C1A 0.0480(9) 0.0497(10) 0.0533(10) 0.0083(8) -0.0055(8) -0.0072(7)
C2A 0.0546(11) 0.0800(14) 0.0567(12) 0.0041(10) 0.0119(9) -0.0079(10)
C3A 0.0717(13) 0.0475(10) 0.0624(12) 0.0096(9) -0.0007(10) 0.0007(9)
C1B 0.0320(7) 0.0428(8) 0.0367(8) -0.0018(6) -0.0030(6) -0.0042(6)
C2B 0.0462(9) 0.0484(9) 0.0465(9) 0.0030(7) 0.0038(7) 0.0042(7)
C3B 0.0565(11) 0.0631(12) 0.0616(12) -0.0057(9) 0.0094(9) 0.0153(9)
C4B 0.0451(10) 0.0880(15) 0.0552(11) -0.0158(10) 0.0135(8) -0.0060(9)
C5B 0.0565(11) 0.0745(13) 0.0453(10) -0.0055(9) 0.0102(8) -0.0257(9)
C6B 0.0506(9) 0.0486(9) 0.0439(9) -0.0014(7) -0.0014(7) -0.0143(7)
C7B 0.0307(7) 0.0432(9) 0.0416(8) -0.0039(6) -0.0052(6) -0.0037(6)
O8B 0.0419(6) 0.0413(6) 0.0652(8) -0.0100(5) 0.0006(5) -0.0020(5)
O9B 0.0429(6) 0.0474(7) 0.0490(7) -0.0011(5) 0.0092(5) -0.0041(5)
O10B 0.0937(11) 0.0456(8) 0.0739(10) 0.0139(7) 0.0306(9) 0.0143(7)

_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
N1A C1A 1.310(2) . ?
N1A C3A 1.350(3) . ?
N1A H1A 0.92(3) . ?
N2A C1A 1.319(2) . ?
N2A C2A 1.344(3) . ?
N2A H2A 0.94(3) . ?
C1A H1AA 0.9400 . ?
C2A C3A 1.317(3) . ?
C2A H2AA 0.9400 . ?
C3A H3AA 0.9400 . ?
C1B C6B 1.392(2) . ?
C1B C2B 1.398(2) . ?
C1B C7B 1.494(2) . ?
C2B O10B 1.349(2) . ?
C2B C3B 1.387(2) . ?
C3B C4B 1.365(3) . ?
C3B H3B 0.9400 . ?
C4B C5B 1.378(3) . ?
C4B H4B 0.9400 . ?
C5B C6B 1.379(3) . ?
C5B H5B 0.9400 . ?
C6B H6B 0.9400 . ?
C7B O8B 1.2449(19) . ?
C7B O9B 1.2764(19) . ?
O10B H10B 1.01(3) . ?

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
C1A N1A C3A 108.53(16) . . ?
C1A N1A H1A 123.6(16) . . ?
C3A N1A H1A 127.9(16) . . ?
C1A N2A C2A 107.99(16) . . ?
C1A N2A H2A 128.6(17) . . ?
C2A N2A H2A 123.4(17) . . ?
N1A C1A N2A 108.30(16) . . ?
N1A C1A H1AA 125.8 . . ?
N2A C1A H1AA 125.8 . . ?
C3A C2A N2A 108.01(18) . . ?
C3A C2A H2AA 126.0 . . ?
N2A C2A H2AA 126.0 . . ?
C2A C3A N1A 107.17(18) . . ?
C2A C3A H3AA 126.4 . . ?
N1A C3A H3AA 126.4 . . ?
C6B C1B C2B 118.09(15) . . ?
C6B C1B C7B 120.97(15) . . ?
C2B C1B C7B 120.94(14) . . ?
O10B C2B C3B 117.92(16) . . ?
O10B C2B C1B 121.75(15) . . ?
C3B C2B C1B 120.33(16) . . ?
C4B C3B C2B 120.20(18) . . ?
C4B C3B H3B 119.9 . . ?
C2B C3B H3B 119.9 . . ?
C3B C4B C5B 120.67(17) . . ?
C3B C4B H4B 119.7 . . ?
C5B C4B H4B 119.7 . . ?
C4B C5B C6B 119.49(17) . . ?
C4B C5B H5B 120.3 . . ?
C6B C5B H5B 120.3 . . ?
C5B C6B C1B 121.19(17) . . ?
C5B C6B H6B 119.4 . . ?
C1B C6B H6B 119.4 . . ?
O8B C7B O9B 122.41(15) . . ?
O8B C7B C1B 120.31(14) . . ?
O9B C7B C1B 117.27(13) . . ?
C2B O10B H10B 101.5(15) . . ?

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
C3A N1A C1A N2A 0.1(2) . . . . ?
C2A N2A C1A N1A 0.1(2) . . . . ?
C1A N2A C2A C3A -0.3(2) . . . . ?
N2A C2A C3A N1A 0.3(2) . . . . ?
C1A N1A C3A C2A -0.2(2) . . . . ?
C6B C1B C2B O10B -179.27(16) . . . . ?
C7B C1B C2B O10B -0.2(3) . . . . ?
C6B C1B C2B C3B 1.6(2) . . . . ?
C7B C1B C2B C3B -179.30(16) . . . . ?
O10B C2B C3B C4B -179.71(19) . . . . ?
C1B C2B C3B C4B -0.5(3) . . . . ?
C2B C3B C4B C5B -0.8(3) . . . . ?
C3B C4B C5B C6B 1.0(3) . . . . ?
C4B C5B C6B C1B 0.1(3) . . . . ?
C2B C1B C6B C5B -1.4(2) . . . . ?
C7B C1B C6B C5B 179.52(15) . . . . ?
C6B C1B C7B O8B -6.2(2) . . . . ?
C2B C1B C7B O8B 174.73(15) . . . . ?
C6B C1B C7B O9B 172.89(14) . . . . ?
C2B C1B C7B O9B -6.2(2) . . . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.050

_shelx_res_file                  
;
TITL al_imid-salicyl_240_fiol_a.res in Pbca
    shelx.res
    created by SHELXL-2018/3 at 15:40:11 on 15-Jul-2024
REM Old TITL al_imid-salicyl_240_fiol_a.res in Pbca
REM SHELXT solution in Pbca: R1 0.167, Rweak 0.008, Alpha 0.016
REM <I/s> 0.554 for 308 systematic absences, Orientation as input
REM Formula found by SHELXT: C10 N3 O2
CELL 0.71073 11.0988 10.9361 16.4701 90 90 90
ZERR 8 0.0006 0.0005 0.0009 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O
UNIT 80 80 16 24

L.S. 10
PLAN  20
TEMP -33
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
OMIT 0 0 2
OMIT 6 3 9
OMIT 1 0 2
REM <olex2.extras>
REM <HklSrc "%.\\AL_IMID-salicyl_240_fiol.hkl">
REM </olex2.extras>

WGHT    0.049300    0.800800
EXTI    0.007474
FVAR       0.44607
N1A   3    0.210620    0.556017    0.523235    11.00000    0.04066    0.05912 =
         0.04937   -0.00426    0.00020    0.01167
H1A   2    0.274471    0.526353    0.493809    11.00000    0.09348
N2A   3    0.078132    0.680967    0.566629    11.00000    0.04714    0.05260 =
         0.06000   -0.01272   -0.00467    0.01443
H2A   2    0.030914    0.750367    0.575968    11.00000    0.09759
C1A   1    0.173604    0.669616    0.519549    11.00000    0.04801    0.04968 =
         0.05330    0.00825   -0.00553   -0.00716
AFIX  43
H1AA  2    0.209018    0.732306    0.488645    11.00000   -1.20000
AFIX   0
C2A   1    0.055675    0.571466    0.600470    11.00000    0.05462    0.08000 =
         0.05671    0.00406    0.01193   -0.00788
AFIX  43
H2AA  2   -0.007113    0.553548    0.636879    11.00000   -1.20000
AFIX   0
C3A   1    0.137057    0.493698    0.573674    11.00000    0.07169    0.04750 =
         0.06237    0.00959   -0.00075    0.00068
AFIX  43
H3AA  2    0.142831    0.410382    0.587153    11.00000   -1.20000
AFIX   0

C1B   1    0.538122    0.484935    0.340270    11.00000    0.03202    0.04282 =
         0.03674   -0.00176   -0.00300   -0.00419
C2B   1    0.573243    0.362403    0.335684    11.00000    0.04618    0.04841 =
         0.04647    0.00300    0.00380    0.00421
C3B   1    0.661053    0.326205    0.280816    11.00000    0.05650    0.06313 =
         0.06157   -0.00572    0.00938    0.01526
AFIX  43
H3B   2    0.684757    0.243769    0.278364    11.00000   -1.20000
AFIX   0
C4B   1    0.713152    0.409887    0.230376    11.00000    0.04509    0.08801 =
         0.05516   -0.01577    0.01346   -0.00600
AFIX  43
H4B   2    0.773320    0.384776    0.193833    11.00000   -1.20000
AFIX   0
C5B   1    0.678449    0.530857    0.232466    11.00000    0.05650    0.07451 =
         0.04530   -0.00551    0.01021   -0.02569
AFIX  43
H5B   2    0.713775    0.587803    0.196957    11.00000   -1.20000
AFIX   0
C6B   1    0.591484    0.567723    0.287064    11.00000    0.05061    0.04863 =
         0.04388   -0.00142   -0.00137   -0.01430
AFIX  43
H6B   2    0.567822    0.650230    0.288371    11.00000   -1.20000
AFIX   0
C7B   1    0.444653    0.525555    0.399729    11.00000    0.03074    0.04317 =
         0.04158   -0.00388   -0.00521   -0.00368
O8B   4    0.420472    0.636117    0.407376    11.00000    0.04188    0.04127 =
         0.06520   -0.00999    0.00062   -0.00198
O9B   4    0.390959    0.442646    0.440548    11.00000    0.04285    0.04738 =
         0.04901   -0.00108    0.00921   -0.00413
O10B  4    0.524906    0.276298    0.384460    11.00000    0.09366    0.04563 =
         0.07388    0.01385    0.03056    0.01426
H10B  2    0.462884    0.325474    0.415295    11.00000    0.09495

HKLF 4




REM  al_imid-salicyl_240_fiol_a.res in Pbca
REM wR2 = 0.1362, GooF = S = 1.074, Restrained GooF = 1.074 for all data
REM R1 = 0.0493 for 1913 Fo > 4sig(Fo) and 0.0695 for all 2584 data
REM 149 parameters refined using 0 restraints

END

WGHT      0.0493      0.8008

REM Highest difference peak  0.323,  deepest hole -0.181,  1-sigma level  0.050
Q1    1   0.2365  0.6271  0.5227  11.00000  0.05    0.32
Q2    1   0.1908  0.5205  0.5614  11.00000  0.05    0.25
Q3    1   0.1416  0.6960  0.5577  11.00000  0.05    0.24
Q4    1   0.1185  0.5447  0.6081  11.00000  0.05    0.20
Q5    1   0.6693  0.3625  0.2422  11.00000  0.05    0.19
Q6    1   0.6174  0.5547  0.2420  11.00000  0.05    0.18
Q7    1   0.5017  0.4977  0.3698  11.00000  0.05    0.17
Q8    1   0.6778  0.4657  0.2272  11.00000  0.05    0.17
Q9    1   0.0830  0.6411  0.5976  11.00000  0.05    0.16
Q10   1   0.2418  0.5213  0.5018  11.00000  0.05    0.16
Q11   1   0.4231  0.3801  0.4442  11.00000  0.05    0.15
Q12   1   0.5339  0.4276  0.3323  11.00000  0.05    0.15
Q13   1   0.7131  0.6405  0.2217  11.00000  0.05    0.14
Q14   1   0.3654  0.3821  0.3887  11.00000  0.05    0.14
Q15   1   0.4600  0.6736  0.4051  11.00000  0.05    0.14
Q16   1   0.2632  0.7110  0.4869  11.00000  0.05    0.14
Q17   1   0.2240  0.3925  0.5589  11.00000  0.05    0.14
Q18   1   0.0852  0.3872  0.5737  11.00000  0.05    0.14
Q19   1   0.4547  0.7075  0.3736  11.00000  0.05    0.14
Q20   1   0.5780  0.5223  0.3224  11.00000  0.05    0.14
;
_shelx_res_checksum              67870

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: AcOEt'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2371022'
loop_
_audit_author_name
_audit_author_address
'Andrzej Gzella'
;Poznan University of Medical Sciences
Poland
;
_audit_update_record             
;
2024-07-15 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
Imidazolium 2-hydroxybenzoate
;
_chemical_name_common            ?
_chemical_melting_point          401-403
_chemical_formula_moiety         'C7 H5 O3^-^, C3 H5 N2^+^'
_chemical_formula_sum            'C10 H10 N2 O3'
_chemical_formula_weight         206.20

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.0676(5)
_cell_length_b                   11.0227(5)
_cell_length_c                   16.1520(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1970.45(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    6426
_cell_measurement_theta_min      4.27
_cell_measurement_theta_max      29.34

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69955
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3991

_diffrn_reflns_number            16383
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         29.51
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2561
_reflns_number_gt                2214
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
; 
WINGX (Farrugia, 2012), OLEX2 v1.2-alpha (Dolomanov et al., 2009), 
PLATON (Spek, 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+1.0147P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2561
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1A N 0.79092(9) 0.55275(9) 0.52409(6) 0.0197(2) Uani 1 1 d . . . . .
H1A H 0.7268(18) 0.5198(17) 0.4950(12) 0.046(5) Uiso 1 1 d . . . . .
N2A N 0.92137(9) 0.68362(10) 0.56667(7) 0.0222(2) Uani 1 1 d . . . . .
H2A H 0.9666(18) 0.7563(18) 0.5740(12) 0.047(5) Uiso 1 1 d . . . . .
C1A C 0.82421(11) 0.66793(11) 0.51950(8) 0.0210(2) Uani 1 1 d . . . . .
H1AA H 0.785220 0.729070 0.487807 0.025 Uiso 1 1 calc R U . . .
C2A C 0.95040(12) 0.57509(12) 0.60246(8) 0.0257(3) Uani 1 1 d . . . . .
H2AA H 1.015755 0.560319 0.639234 0.031 Uiso 1 1 calc R U . . .
C3A C 0.86902(12) 0.49296(12) 0.57584(8) 0.0242(3) Uani 1 1 d . . . . .
H3AA H 0.866278 0.409430 0.590208 0.029 Uiso 1 1 calc R U . . .
C1B C 0.45963(10) 0.48420(10) 0.34089(7) 0.0169(2) Uani 1 1 d . . . . .
C2B C 0.42485(11) 0.36186(11) 0.33703(7) 0.0210(2) Uani 1 1 d . . . . .
C3B C 0.33475(12) 0.32505(12) 0.28212(8) 0.0265(3) Uani 1 1 d . . . . .
H3B H 0.311110 0.242251 0.280017 0.032 Uiso 1 1 calc R U . . .
C4B C 0.27997(11) 0.40852(13) 0.23092(8) 0.0272(3) Uani 1 1 d . . . . .
H4B H 0.217916 0.383020 0.194197 0.033 Uiso 1 1 calc R U . . .
C5B C 0.31466(12) 0.52972(12) 0.23248(8) 0.0259(3) Uani 1 1 d . . . . .
H5B H 0.277453 0.586710 0.196470 0.031 Uiso 1 1 calc R U . . .
C6B C 0.40395(11) 0.56661(11) 0.28701(7) 0.0213(3) Uani 1 1 d . . . . .
H6B H 0.427893 0.649365 0.287897 0.026 Uiso 1 1 calc R U . . .
C7B C 0.55461(10) 0.52549(10) 0.40071(7) 0.0171(2) Uani 1 1 d . . . . .
O8B O 0.57871(7) 0.63572(7) 0.40757(5) 0.0212(2) Uani 1 1 d . . . . .
O9B O 0.60949(7) 0.44322(7) 0.44223(5) 0.01996(19) Uani 1 1 d . . . . .
O10B O 0.47551(10) 0.27651(8) 0.38599(6) 0.0312(2) Uani 1 1 d . . . . .
H10B H 0.534(2) 0.3235(19) 0.4175(13) 0.057(6) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1A 0.0166(5) 0.0214(5) 0.0210(5) -0.0013(4) -0.0006(4) -0.0026(4)
N2A 0.0199(5) 0.0227(5) 0.0240(5) -0.0039(4) 0.0016(4) -0.0047(4)
C1A 0.0197(6) 0.0202(5) 0.0230(6) 0.0014(4) 0.0020(4) 0.0010(4)
C2A 0.0217(6) 0.0320(7) 0.0234(6) 0.0014(5) -0.0030(5) 0.0022(5)
C3A 0.0258(6) 0.0219(6) 0.0248(6) 0.0034(5) 0.0003(5) 0.0014(5)
C1B 0.0142(5) 0.0197(5) 0.0169(5) -0.0009(4) 0.0021(4) 0.0016(4)
C2B 0.0207(6) 0.0226(6) 0.0198(6) 0.0020(4) -0.0007(4) -0.0024(4)
C3B 0.0248(6) 0.0291(6) 0.0256(6) -0.0020(5) -0.0024(5) -0.0079(5)
C4B 0.0182(6) 0.0408(7) 0.0226(6) -0.0058(5) -0.0037(5) 0.0009(5)
C5B 0.0242(6) 0.0331(7) 0.0202(6) -0.0023(5) -0.0028(5) 0.0112(5)
C6B 0.0218(6) 0.0220(6) 0.0202(6) -0.0011(4) 0.0012(4) 0.0056(4)
C7B 0.0133(5) 0.0197(5) 0.0181(5) -0.0017(4) 0.0035(4) 0.0008(4)
O8B 0.0183(4) 0.0174(4) 0.0280(5) -0.0033(3) 0.0008(3) 0.0006(3)
O9B 0.0179(4) 0.0197(4) 0.0223(4) -0.0001(3) -0.0035(3) 0.0010(3)
O10B 0.0412(6) 0.0204(5) 0.0319(5) 0.0065(4) -0.0144(4) -0.0070(4)

_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
N1A C1A 1.3240(15) . ?
N1A C3A 1.3712(16) . ?
N1A H1A 0.93(2) . ?
N2A C1A 1.3292(16) . ?
N2A C2A 1.3670(17) . ?
N2A H2A 0.95(2) . ?
C1A H1AA 0.9500 . ?
C2A C3A 1.3474(19) . ?
C2A H2AA 0.9500 . ?
C3A H3AA 0.9500 . ?
C1B C6B 1.4008(16) . ?
C1B C2B 1.4039(16) . ?
C1B C7B 1.4985(16) . ?
C2B O10B 1.3508(15) . ?
C2B C3B 1.3949(17) . ?
C3B C4B 1.3777(19) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3903(19) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3848(18) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B O8B 1.2489(14) . ?
C7B O9B 1.2810(14) . ?
O10B H10B 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
C1A N1A C3A 108.64(10) . . ?
C1A N1A H1A 124.1(12) . . ?
C3A N1A H1A 127.2(12) . . ?
C1A N2A C2A 108.58(10) . . ?
C1A N2A H2A 127.3(12) . . ?
C2A N2A H2A 124.1(12) . . ?
N1A C1A N2A 108.53(11) . . ?
N1A C1A H1AA 125.7 . . ?
N2A C1A H1AA 125.7 . . ?
C3A C2A N2A 107.21(11) . . ?
C3A C2A H2AA 126.4 . . ?
N2A C2A H2AA 126.4 . . ?
C2A C3A N1A 107.04(11) . . ?
C2A C3A H3AA 126.5 . . ?
N1A C3A H3AA 126.5 . . ?
C6B C1B C2B 118.33(11) . . ?
C6B C1B C7B 120.81(10) . . ?
C2B C1B C7B 120.85(10) . . ?
O10B C2B C3B 117.80(11) . . ?
O10B C2B C1B 121.95(11) . . ?
C3B C2B C1B 120.25(11) . . ?
C4B C3B C2B 120.13(12) . . ?
C4B C3B H3B 119.9 . . ?
C2B C3B H3B 119.9 . . ?
C3B C4B C5B 120.62(12) . . ?
C3B C4B H4B 119.7 . . ?
C5B C4B H4B 119.7 . . ?
C6B C5B C4B 119.39(12) . . ?
C6B C5B H5B 120.3 . . ?
C4B C5B H5B 120.3 . . ?
C5B C6B C1B 121.25(12) . . ?
C5B C6B H6B 119.4 . . ?
C1B C6B H6B 119.4 . . ?
O8B C7B O9B 122.75(11) . . ?
O8B C7B C1B 120.17(10) . . ?
O9B C7B C1B 117.07(10) . . ?
C2B O10B H10B 102.3(12) . . ?

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
C3A N1A C1A N2A 0.07(14) . . . . ?
C2A N2A C1A N1A -0.16(14) . . . . ?
C1A N2A C2A C3A 0.18(15) . . . . ?
N2A C2A C3A N1A -0.13(14) . . . . ?
C1A N1A C3A C2A 0.04(14) . . . . ?
C6B C1B C2B O10B 178.98(11) . . . . ?
C7B C1B C2B O10B -0.57(18) . . . . ?
C6B C1B C2B C3B -1.63(17) . . . . ?
C7B C1B C2B C3B 178.82(11) . . . . ?
O10B C2B C3B C4B 179.87(12) . . . . ?
C1B C2B C3B C4B 0.46(19) . . . . ?
C2B C3B C4B C5B 0.8(2) . . . . ?
C3B C4B C5B C6B -0.94(19) . . . . ?
C4B C5B C6B C1B -0.28(18) . . . . ?
C2B C1B C6B C5B 1.54(17) . . . . ?
C7B C1B C6B C5B -178.90(11) . . . . ?
C6B C1B C7B O8B 5.46(16) . . . . ?
C2B C1B C7B O8B -175.00(11) . . . . ?
C6B C1B C7B O9B -173.44(10) . . . . ?
C2B C1B C7B O9B 6.10(16) . . . . ?

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
N2A H2A O8B 0.95(2) 1.74(2) 2.6779(13) 165.7(18) 4_566 yes
N1A H1A O9B 0.93(2) 1.77(2) 2.6904(13) 174.6(18) . yes
O10B H10B O9B 0.98(2) 1.61(2) 2.5300(12) 155.3(19) . yes

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.055

_shelx_res_file                  
;
TITL al_imid-salicyl_100_fiol_a.res in Pbca
    shelx.res
    created by SHELXL-2018/3 at 13:57:53 on 15-Jul-2024
REM Old TITL AL_IMID-salicyl_100_fiol in Pbca
REM SHELXT solution in Pbca
REM R1 0.123, Rweak 0.098, Alpha 0.010, Orientation as input
REM Formula found by SHELXT: C10 N2 O3
CELL 0.71073 11.067578 11.022692 16.151998 90 90 90
ZERR 8 0.000455 0.000489 0.000748 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O
UNIT 80 80 16 24
EQIV $1 0.5+X,1.5-Y,1-Z

L.S. 10
PLAN  20
TEMP -173
CONF
MPLA N1A N2A C1A C2A C3A
MPLA C1B C2B C3B C4B C5B C6B
MPLA C7B O8B O9B

HTAB N2A O8B_$1
HTAB N1A O9B
HTAB O10B O9B
BOND $H
list 4
fmap 2
acta
more -3
OMIT 0 0 2
OMIT 6 3 9

REM <olex2.extras>
REM <HklSrc "%.\\AL_IMID-salicyl_100_fiol.hkl">
REM </olex2.extras>

WGHT    0.041200    1.014700
FVAR       4.01554
N1A   3    0.790918    0.552752    0.524094    11.00000    0.01664    0.02136 =
         0.02105   -0.00128   -0.00058   -0.00264
H1A   2    0.726768    0.519823    0.495043    11.00000    0.04551
N2A   3    0.921369    0.683620    0.566670    11.00000    0.01995    0.02273 =
         0.02399   -0.00392    0.00157   -0.00468
H2A   2    0.966610    0.756334    0.574009    11.00000    0.04659
C1A   1    0.824215    0.667925    0.519497    11.00000    0.01970    0.02022 =
         0.02303    0.00136    0.00196    0.00103
AFIX  43
H1AA  2    0.785220    0.729070    0.487807    11.00000   -1.20000
AFIX   0
C2A   1    0.950401    0.575086    0.602459    11.00000    0.02167    0.03204 =
         0.02341    0.00141   -0.00297    0.00222
AFIX  43
H2AA  2    1.015755    0.560319    0.639234    11.00000   -1.20000
AFIX   0
C3A   1    0.869023    0.492960    0.575841    11.00000    0.02583    0.02185 =
         0.02485    0.00343    0.00032    0.00142
AFIX  43
H3AA  2    0.866278    0.409430    0.590208    11.00000   -1.20000
AFIX   0

C1B   1    0.459634    0.484203    0.340895    11.00000    0.01418    0.01970 =
         0.01688   -0.00090    0.00207    0.00165
C2B   1    0.424847    0.361855    0.337029    11.00000    0.02072    0.02258 =
         0.01980    0.00202   -0.00070   -0.00243
C3B   1    0.334749    0.325047    0.282116    11.00000    0.02478    0.02907 =
         0.02557   -0.00198   -0.00235   -0.00791
AFIX  43
H3B   2    0.311110    0.242251    0.280017    11.00000   -1.20000
AFIX   0
C4B   1    0.279974    0.408519    0.230916    11.00000    0.01818    0.04081 =
         0.02255   -0.00582   -0.00371    0.00094
AFIX  43
H4B   2    0.217916    0.383020    0.194197    11.00000   -1.20000
AFIX   0
C5B   1    0.314661    0.529720    0.232480    11.00000    0.02424    0.03315 =
         0.02017   -0.00228   -0.00276    0.01123
AFIX  43
H5B   2    0.277453    0.586710    0.196470    11.00000   -1.20000
AFIX   0
C6B   1    0.403950    0.566609    0.287012    11.00000    0.02180    0.02204 =
         0.02016   -0.00114    0.00117    0.00564
AFIX  43
H6B   2    0.427893    0.649365    0.287897    11.00000   -1.20000
AFIX   0
C7B   1    0.554606    0.525487    0.400712    11.00000    0.01332    0.01974 =
         0.01811   -0.00168    0.00352    0.00076
O8B   4    0.578709    0.635721    0.407575    11.00000    0.01826    0.01745 =
         0.02798   -0.00334    0.00083    0.00059
O9B   4    0.609494    0.443215    0.442227    11.00000    0.01786    0.01970 =
         0.02231   -0.00011   -0.00355    0.00105
O10B  4    0.475509    0.276506    0.385987    11.00000    0.04121    0.02040 =
         0.03195    0.00655   -0.01438   -0.00704
H10B  2    0.534473    0.323455    0.417523    11.00000    0.05672

HKLF 4




REM  al_imid-salicyl_100_fiol_a.res in Pbca
REM wR2 = 0.1037, GooF = S = 1.084, Restrained GooF = 1.084 for all data
REM R1 = 0.0400 for 2214 Fo > 4sig(Fo) and 0.0476 for all 2561 data
REM 148 parameters refined using 0 restraints

END

WGHT      0.0408      1.0345

REM Highest difference peak  0.291,  deepest hole -0.267,  1-sigma level  0.055
Q1    1   0.8964  0.5372  0.6038  11.00000  0.05    0.29
Q2    1   0.3870  0.3460  0.3046  11.00000  0.05    0.27
Q3    1   0.8181  0.5201  0.5562  11.00000  0.05    0.26
Q4    1   0.4535  0.4233  0.3354  11.00000  0.05    0.26
Q5    1   0.5024  0.5019  0.3712  11.00000  0.05    0.25
Q6    1   0.7837  0.6193  0.5314  11.00000  0.05    0.24
Q7    1   0.3728  0.5307  0.2475  11.00000  0.05    0.23
Q8    1   0.9387  0.6273  0.5808  11.00000  0.05    0.22
Q9    1   0.9257  0.5248  0.5844  11.00000  0.05    0.21
Q10   1   0.3219  0.3659  0.2506  11.00000  0.05    0.21
Q11   1   0.4317  0.5205  0.3064  11.00000  0.05    0.20
Q12   1   0.3216  0.4671  0.2236  11.00000  0.05    0.20
Q13   1   0.8654  0.6805  0.5531  11.00000  0.05    0.20
Q14   1   1.0020  0.3505  0.5445  11.00000  0.05    0.18
Q15   1   0.4596  0.6619  0.2757  11.00000  0.05    0.16
Q16   1   0.8981  0.6693  0.5192  11.00000  0.05    0.15
Q17   1   1.1229  0.6236  0.6227  11.00000  0.05    0.14
Q18   1   0.9007  0.6483  0.6075  11.00000  0.05    0.14
Q19   1   0.9389  0.6199  0.4992  11.00000  0.05    0.14
Q20   1   0.6668  0.8430  0.4632  11.00000  0.05    0.14
;
_shelx_res_checksum              74259

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: AcOEt'
####################################################################### 
# 
# 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_227GPa
_database_code_depnum_ccdc_archive 'CCDC 2355854'
loop_
_audit_author_name
_audit_author_address
'Michalina Rusek'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-05-16 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_audit_creation_date             2024-05-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT029_227GPa              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.337 Why?  
RESPONSE: It is due to high-pressure conditions
;
_vrf_PLAT026_227GPa              
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        33% Check 
RESPONSE: It is due to high-pressure conditions
;
_vrf_PLAT084_227GPa              
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.38 Report
RESPONSE: It is due to high-pressure conditions
;
_vrf_PLAT241_227GPa              
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         C9 Check 
RESPONSE: It is due to high-pressure conditions
;
_vrf_PLAT340_227GPa              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02425 Ang.  
RESPONSE: It is due to high-pressure conditions
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H5 O3, C3 H5 N2'
_chemical_formula_sum            'C10 H10 N2 O3'
_chemical_formula_weight         206.20
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.540(5)
_cell_length_b                   10.49(4)
_cell_length_c                   14.153(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1713(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    581
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       2270000(2)
_cell_measurement_theta_max      27.269
_cell_measurement_theta_min      4.956
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Data were collected at room temperature and pressure of 2.27(2) GPa
 (2270000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1118
_diffrn_reflns_av_unetI/netI     0.0847
_diffrn_reflns_Laue_measured_fraction_full 0.337
_diffrn_reflns_Laue_measured_fraction_max 0.299
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5289
_diffrn_reflns_point_group_measured_fraction_full 0.337
_diffrn_reflns_point_group_measured_fraction_max 0.299
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.269
_diffrn_reflns_theta_min         4.956
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.337
_diffrn_measured_fraction_theta_max 0.299
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                189
_reflns_number_total             576
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         576
_refine_ls_number_restraints     92
_refine_ls_R_factor_all          0.2344
_refine_ls_R_factor_gt           0.0968
_refine_ls_restrained_S_all      0.935
_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)+(0.1859P)²+1.9547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2490
_refine_ls_wR_factor_ref         0.3807
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 H3A-O2
 1.9 with sigma of 0.01
 H3A-C8_$1
 2.6 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of
0.004 and sigma for terminal atoms of 0.008
Uanis(C7) \\sim Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.008
Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(C6) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.004 and sigma
for terminal atoms of 0.008
Uanis(O3) \\sim Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.008
Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C8) \\sim
Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.008
Uanis(N1) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(N2) \\sim
Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(N1) \\sim Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.008
4.a :
 N1(C8,N2,C10,C9)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), N1(H1), C8(H8), N2(H2), C10(H10), C9(H9)
4.c Fitted hexagon refined as free rotating group:
 C2(C3,C4,C5,C6,C1)
4.d Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C2 C 0.5649(9) 0.351(2) 0.3316(6) 0.102(6) Uani 1 1 d G U . . .
C3 C 0.6533(9) 0.3084(19) 0.2730(8) 0.096(5) Uani 1 1 d G U . . .
H3 H 0.671291 0.222057 0.270766 0.115 Uiso 1 1 calc R U . . .
C4 C 0.7147(7) 0.395(2) 0.2176(6) 0.094(6) Uani 1 1 d G U . . .
H4 H 0.773793 0.365759 0.178335 0.112 Uiso 1 1 calc R U . . .
C5 C 0.6878(8) 0.524(2) 0.2209(7) 0.102(6) Uani 1 1 d G U . . .
H5 H 0.728855 0.581224 0.183825 0.123 Uiso 1 1 calc R U . . .
C6 C 0.5994(9) 0.5666(19) 0.2795(8) 0.094(5) Uani 1 1 d G U . . .
H6 H 0.581414 0.652989 0.281746 0.113 Uiso 1 1 calc R U . . .
C1 C 0.5380(7) 0.481(2) 0.3349(6) 0.082(5) Uani 1 1 d G U . . .
C7 C 0.4425(16) 0.527(7) 0.4034(14) 0.088(8) Uani 1 1 d . U . . .
O1 O 0.4197(11) 0.647(3) 0.4040(8) 0.105(6) Uani 1 1 d . U . . .
O2 O 0.3927(8) 0.439(2) 0.4463(7) 0.090(5) Uani 1 1 d D U . . .
O3 O 0.5075(9) 0.254(2) 0.3786(8) 0.127(5) Uani 1 1 d . U . . .
H3A H 0.445161 0.280507 0.398434 0.191 Uiso 1 1 calc DR U . . .
N1 N 0.2164(8) 0.560(2) 0.5290(6) 0.084(5) Uani 1 1 d G U . . .
H1 H 0.280311 0.534133 0.504128 0.100 Uiso 1 1 calc R U . . .
C8 C 0.1792(15) 0.676(2) 0.5309(8) 0.114(8) Uani 1 1 d G U . . .
H8 H 0.216805 0.746339 0.505668 0.137 Uiso 1 1 calc R U . . .
N2 N 0.0806(13) 0.676(2) 0.5740(9) 0.128(7) Uani 1 1 d G U . . .
H2 H 0.038213 0.742403 0.584453 0.154 Uiso 1 1 calc R U . . .
C10 C 0.0569(11) 0.561(3) 0.5987(7) 0.106(8) Uani 1 1 d G U . . .
H10 H -0.009030 0.534325 0.630954 0.128 Uiso 1 1 calc R U . . .
C9 C 0.1408(15) 0.489(2) 0.5709(8) 0.153(9) Uani 1 1 d G U . . .
H9 H 0.145930 0.401018 0.579492 0.184 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.102(7) 0.102(8) 0.101(7) -0.002(4) -0.003(4) 0.000(4)
C3 0.096(6) 0.096(7) 0.097(6) 0.001(4) 0.002(4) 0.001(4)
C4 0.094(7) 0.094(8) 0.093(7) -0.001(4) -0.002(4) -0.001(4)
C5 0.102(7) 0.103(8) 0.102(7) -0.003(4) 0.000(4) -0.001(4)
C6 0.096(6) 0.094(7) 0.093(6) 0.001(4) -0.002(4) -0.001(4)
C1 0.085(6) 0.082(7) 0.079(6) -0.001(4) -0.004(4) 0.000(4)
C7 0.088(8) 0.087(9) 0.087(8) -0.001(4) -0.004(4) -0.001(4)
O1 0.095(6) 0.106(12) 0.113(8) -0.006(8) -0.012(4) -0.001(8)
O2 0.087(5) 0.092(11) 0.091(5) 0.005(7) -0.001(5) 0.001(7)
O3 0.129(7) 0.125(11) 0.127(6) 0.000(8) 0.013(6) 0.001(8)
N1 0.083(5) 0.083(7) 0.085(5) -0.002(4) 0.001(3) 0.002(4)
C8 0.112(8) 0.114(9) 0.115(8) 0.001(4) 0.001(4) -0.001(4)
N2 0.127(7) 0.128(8) 0.129(7) 0.001(4) 0.002(4) 0.002(4)
C10 0.106(8) 0.106(9) 0.107(8) 0.001(4) 0.006(4) -0.001(4)
C9 0.153(9) 0.153(10) 0.153(9) 0.000(4) -0.004(4) 0.002(4)

_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
C2 C3 1.3900 . ?
C2 C1 1.3900 . ?
C2 O3 1.39(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 H5 0.9300 . ?
C5 C6 1.3900 . ?
C6 H6 0.9300 . ?
C6 C1 1.3900 . ?
C1 C7 1.55(2) . ?
C7 O1 1.29(7) . ?
C7 O2 1.24(5) . ?
O3 H3A 0.8200 . ?
N1 H1 0.8600 . ?
N1 C8 1.291(10) . ?
N1 C9 1.291(9) . ?
C8 H8 0.9300 . ?
C8 N2 1.291(8) . ?
N2 H2 0.8600 . ?
N2 C10 1.291(10) . ?
C10 H10 0.9300 . ?
C10 C9 1.291(9) . ?
C9 H9 0.9300 . ?

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
C3 C2 C1 120.0 . . ?
O3 C2 C3 113.5(13) . . ?
O3 C2 C1 126.5(13) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 C5 120.0 . . ?
C1 C6 H6 120.0 . . ?
C2 C1 C7 119(3) . . ?
C6 C1 C2 120.0 . . ?
C6 C1 C7 121(3) . . ?
O1 C7 C1 117(4) . . ?
O2 C7 C1 114(5) . . ?
O2 C7 O1 129(2) . . ?
C2 O3 H3A 109.5 . . ?
C8 N1 H1 126.0 . . ?
C8 N1 C9 108.0 . . ?
C9 N1 H1 126.0 . . ?
N1 C8 H8 126.0 . . ?
N1 C8 N2 108.0 . . ?
N2 C8 H8 126.0 . . ?
C8 N2 H2 126.0 . . ?
C8 N2 C10 108.0 . . ?
C10 N2 H2 126.0 . . ?
N2 C10 H10 126.0 . . ?
C9 C10 N2 108.0 . . ?
C9 C10 H10 126.0 . . ?
N1 C9 H9 126.0 . . ?
C10 C9 N1 108.0 . . ?
C10 C9 H9 126.0 . . ?

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
C2 C3 C4 C5 0.0 . . . . ?
C2 C1 C7 O1 -179.7(15) . . . . ?
C2 C1 C7 O2 -4.2(19) . . . . ?
C3 C2 C1 C6 0.0 . . . . ?
C3 C2 C1 C7 -177.8(10) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C5 C6 C1 C2 0.0 . . . . ?
C5 C6 C1 C7 177.7(10) . . . . ?
C6 C1 C7 O1 3(2) . . . . ?
C6 C1 C7 O2 178.1(10) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
O3 C2 C3 C4 176.7(10) . . . . ?
O3 C2 C1 C6 -176.3(11) . . . . ?
O3 C2 C1 C7 6.0(14) . . . . ?
N1 C8 N2 C10 0.0 . . . . ?
C8 N1 C9 C10 0.0 . . . . ?
C8 N2 C10 C9 0.0 . . . . ?
N2 C10 C9 N1 0.0 . . . . ?
C9 N1 C8 N2 0.0 . . . . ?
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2371025'
loop_
_audit_author_name
_audit_author_address
'Andrzej Gzella'
;Poznan University of Medical Sciences
Poland
;
_audit_update_record             
;
2024-07-15 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
Imidazolium 2-hydroxybenzoate
;
_chemical_name_common            ?
_chemical_melting_point          401-403
_chemical_formula_moiety         'C7 H5 O3^-^, C3 H5 N2^+^'
_chemical_formula_sum            'C10 H10 N2 O3'
_chemical_formula_weight         206.20

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.0777(11)
_cell_length_b                   10.9375(9)
_cell_length_c                   16.6880(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2022.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    300.0(1)
_cell_measurement_reflns_used    4338
_cell_measurement_theta_min      3.71
_cell_measurement_theta_max      25.99

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.58190
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3991
_diffrn_reflns_number            15447
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.441
_diffrn_reflns_theta_max         29.658
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2617
_reflns_number_gt                1775
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
; 
WINGX (Farrugia, 2012), OLEX2 v1.2-alpha (Dolomanov et al., 2009), 
PLATON (Spek, 2009)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+0.7304P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0121(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2617
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1243
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1A N 0.21074(15) 0.55717(16) 0.47728(10) 0.0623(4) Uani 1 1 d . . . . .
H1A H 0.276(3) 0.528(2) 0.5078(16) 0.111(9) Uiso 1 1 d . . . . .
N2A N 0.07785(16) 0.68039(17) 0.43347(11) 0.0678(5) Uani 1 1 d . . . . .
H2A H 0.031(3) 0.749(3) 0.4247(17) 0.122(10) Uiso 1 1 d . . . . .
C1A C 0.17281(19) 0.66996(18) 0.48062(12) 0.0638(5) Uani 1 1 d . . . . .
H1AA H 0.206888 0.732303 0.511022 0.077 Uiso 1 1 calc R U . . .
C2A C 0.0573(2) 0.5707(2) 0.40018(14) 0.0808(7) Uani 1 1 d . . . . .
H2AA H -0.004127 0.552011 0.364256 0.097 Uiso 1 1 calc R U . . .
C3A C 0.1389(2) 0.4947(2) 0.42709(14) 0.0766(6) Uani 1 1 d . . . . .
H3AA H 0.145856 0.412358 0.413874 0.092 Uiso 1 1 calc R U . . .
C1B C 0.53688(14) 0.48489(15) 0.65964(9) 0.0462(4) Uani 1 1 d . . . . .
C2B C 0.57262(17) 0.36272(17) 0.66447(11) 0.0580(5) Uani 1 1 d . . . . .
C3B C 0.6597(2) 0.3265(2) 0.71900(13) 0.0753(6) Uani 1 1 d . . . . .
H3B H 0.683314 0.245007 0.721467 0.090 Uiso 1 1 calc R U . . .
C4B C 0.7107(2) 0.4101(2) 0.76903(13) 0.0787(7) Uani 1 1 d . . . . .
H4B H 0.769597 0.385146 0.805211 0.094 Uiso 1 1 calc R U . . .
C5B C 0.6763(2) 0.5309(2) 0.76683(12) 0.0739(6) Uani 1 1 d . . . . .
H5B H 0.711106 0.587237 0.801623 0.089 Uiso 1 1 calc R U . . .
C6B C 0.58968(17) 0.56776(18) 0.71243(11) 0.0594(5) Uani 1 1 d . . . . .
H6B H 0.566177 0.649362 0.711024 0.071 Uiso 1 1 calc R U . . .
C7B C 0.44421(15) 0.52521(15) 0.60053(10) 0.0481(4) Uani 1 1 d . . . . .
O8B O 0.41979(12) 0.63587(11) 0.59266(8) 0.0622(4) Uani 1 1 d . . . . .
O9B O 0.39068(11) 0.44243(11) 0.56011(8) 0.0591(4) Uani 1 1 d . . . . .
O10B O 0.52503(17) 0.27656(13) 0.61595(11) 0.0889(6) Uani 1 1 d . . . . .
H10B H 0.460(3) 0.327(3) 0.5849(17) 0.120(10) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1A 0.0514(9) 0.0745(11) 0.0610(9) 0.0052(8) -0.0003(7) 0.0159(8)
N2A 0.0619(10) 0.0649(10) 0.0764(11) 0.0163(9) 0.0059(9) 0.0183(8)
C1A 0.0621(12) 0.0610(11) 0.0682(12) -0.0107(9) 0.0064(9) -0.0093(9)
C2A 0.0710(15) 0.0992(18) 0.0722(14) -0.0060(13) -0.0165(11) -0.0074(13)
C3A 0.0920(17) 0.0593(12) 0.0785(14) -0.0140(10) -0.0011(13) 0.0025(11)
C1B 0.0409(8) 0.0515(9) 0.0460(8) 0.0020(7) 0.0040(6) -0.0052(7)
C2B 0.0573(11) 0.0582(10) 0.0587(10) -0.0028(8) -0.0046(8) 0.0043(8)
C3B 0.0707(13) 0.0765(13) 0.0787(14) 0.0081(11) -0.0139(11) 0.0172(11)
C4B 0.0580(12) 0.1066(18) 0.0716(13) 0.0218(12) -0.0174(10) -0.0090(12)
C5B 0.0731(14) 0.0921(15) 0.0565(11) 0.0059(10) -0.0122(10) -0.0333(12)
C6B 0.0632(11) 0.0600(10) 0.0549(10) 0.0021(8) 0.0003(9) -0.0171(9)
C7B 0.0398(8) 0.0529(9) 0.0517(9) 0.0043(7) 0.0059(7) -0.0051(7)
O8B 0.0549(8) 0.0511(7) 0.0805(9) 0.0126(6) -0.0009(6) -0.0018(6)
O9B 0.0551(8) 0.0602(7) 0.0619(7) 0.0008(6) -0.0115(6) -0.0058(6)
O10B 0.1159(14) 0.0549(8) 0.0960(12) -0.0167(8) -0.0378(10) 0.0160(8)

_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
N1A C1A 1.304(2) . ?
N1A C3A 1.343(3) . ?
N1A H1A 0.94(3) . ?
N2A C1A 1.319(3) . ?
N2A C2A 1.341(3) . ?
N2A H2A 0.93(3) . ?
C1A H1AA 0.9300 . ?
C2A C3A 1.307(3) . ?
C2A H2AA 0.9300 . ?
C3A H3AA 0.9300 . ?
C1B C6B 1.393(2) . ?
C1B C2B 1.396(2) . ?
C1B C7B 1.491(2) . ?
C2B O10B 1.350(2) . ?
C2B C3B 1.384(3) . ?
C3B C4B 1.361(3) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.376(3) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.381(3) . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
C7B O8B 1.247(2) . ?
C7B O9B 1.275(2) . ?
O10B H10B 1.05(3) . ?

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
C1A N1A C3A 108.50(18) . . ?
C1A N1A H1A 123.1(17) . . ?
C3A N1A H1A 128.4(17) . . ?
C1A N2A C2A 107.75(18) . . ?
C1A N2A H2A 127.6(19) . . ?
C2A N2A H2A 124.6(19) . . ?
N1A C1A N2A 108.26(18) . . ?
N1A C1A H1AA 125.9 . . ?
N2A C1A H1AA 125.9 . . ?
C3A C2A N2A 108.0(2) . . ?
C3A C2A H2AA 126.0 . . ?
N2A C2A H2AA 126.0 . . ?
C2A C3A N1A 107.5(2) . . ?
C2A C3A H3AA 126.3 . . ?
N1A C3A H3AA 126.3 . . ?
C6B C1B C2B 117.86(17) . . ?
C6B C1B C7B 121.02(16) . . ?
C2B C1B C7B 121.11(15) . . ?
O10B C2B C3B 117.84(18) . . ?
O10B C2B C1B 121.53(17) . . ?
C3B C2B C1B 120.63(18) . . ?
C4B C3B C2B 120.0(2) . . ?
C4B C3B H3B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C3B C4B C5B 120.9(2) . . ?
C3B C4B H4B 119.5 . . ?
C5B C4B H4B 119.5 . . ?
C4B C5B C6B 119.33(19) . . ?
C4B C5B H5B 120.3 . . ?
C6B C5B H5B 120.3 . . ?
C5B C6B C1B 121.18(19) . . ?
C5B C6B H6B 119.4 . . ?
C1B C6B H6B 119.4 . . ?
O8B C7B O9B 122.18(16) . . ?
O8B C7B C1B 120.41(15) . . ?
O9B C7B C1B 117.40(14) . . ?
C2B O10B H10B 101.4(15) . . ?

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
C3A N1A C1A N2A 0.1(2) . . . . ?
C2A N2A C1A N1A -0.1(2) . . . . ?
C1A N2A C2A C3A 0.2(3) . . . . ?
N2A C2A C3A N1A -0.1(3) . . . . ?
C1A N1A C3A C2A 0.0(3) . . . . ?
C6B C1B C2B O10B 179.42(18) . . . . ?
C7B C1B C2B O10B 0.1(3) . . . . ?
C6B C1B C2B C3B -1.3(3) . . . . ?
C7B C1B C2B C3B 179.32(17) . . . . ?
O10B C2B C3B C4B 179.8(2) . . . . ?
C1B C2B C3B C4B 0.5(3) . . . . ?
C2B C3B C4B C5B 0.5(4) . . . . ?
C3B C4B C5B C6B -0.7(3) . . . . ?
C4B C5B C6B C1B -0.2(3) . . . . ?
C2B C1B C6B C5B 1.2(3) . . . . ?
C7B C1B C6B C5B -179.45(16) . . . . ?
C6B C1B C7B O8B 6.2(2) . . . . ?
C2B C1B C7B O8B -174.52(16) . . . . ?
C6B C1B C7B O9B -172.72(16) . . . . ?
C2B C1B C7B O9B 6.6(2) . . . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.056

_shelx_res_file                  
;
TITL al_imid-salicyl_300_fiol_a.res in Pbca
    shelx.res
    created by SHELXL-2018/3 at 18:16:16 on 15-Jul-2024
REM Old TITL AL_IMID-salicyl_300_fiol in Pbca
REM SHELXT solution in Pbca
REM R1 0.308, Rweak 0.238, Alpha 0.038, Orientation as input
REM Formula found by SHELXT: C10 N O4
CELL 0.71073 11.077673 10.937495 16.688035 90 90 90
ZERR 8 0.001111 0.000891 0.001479 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O
UNIT 80 80 16 24

L.S. 10
PLAN  20
TEMP 27
CONF
BOND $H
list 4
MORE -1
fmap 2
acta

OMIT 7 0 14
OMIT 6 3 9

REM <olex2.extras>
REM <HklSrc "%.\\AL_IMID-salicyl_300_fiol.hkl">
REM </olex2.extras>

WGHT    0.046700    0.730400
EXTI    0.012135
FVAR       4.38071
N1A   3    0.210742    0.557169    0.477278    11.00000    0.05143    0.07454 =
         0.06102    0.00520   -0.00030    0.01586
H1A   2    0.275814    0.527989    0.507836    11.00000    0.11097
N2A   3    0.077849    0.680392    0.433467    11.00000    0.06193    0.06493 =
         0.07642    0.01632    0.00590    0.01825
H2A   2    0.031086    0.749413    0.424735    11.00000    0.12165
C1A   1    0.172811    0.669961    0.480616    11.00000    0.06207    0.06105 =
         0.06815   -0.01070    0.00638   -0.00934
AFIX  43
H1AA  2    0.206888    0.732303    0.511022    11.00000   -1.20000
AFIX   0
C2A   1    0.057342    0.570699    0.400182    11.00000    0.07098    0.09918 =
         0.07218   -0.00605   -0.01645   -0.00745
AFIX  43
H2AA  2   -0.004127    0.552011    0.364256    11.00000   -1.20000
AFIX   0
C3A   1    0.138893    0.494661    0.427085    11.00000    0.09204    0.05926 =
         0.07849   -0.01395   -0.00112    0.00251
AFIX  43
H3AA  2    0.145856    0.412358    0.413874    11.00000   -1.20000
AFIX   0

C1B   1    0.536883    0.484886    0.659642    11.00000    0.04091    0.05155 =
         0.04604    0.00201    0.00398   -0.00516
C2B   1    0.572622    0.362718    0.664470    11.00000    0.05730    0.05816 =
         0.05866   -0.00278   -0.00458    0.00435
C3B   1    0.659667    0.326506    0.719003    11.00000    0.07073    0.07648 =
         0.07865    0.00805   -0.01389    0.01721
AFIX  43
H3B   2    0.683314    0.245007    0.721467    11.00000   -1.20000
AFIX   0
C4B   1    0.710681    0.410068    0.769026    11.00000    0.05801    0.10661 =
         0.07156    0.02176   -0.01745   -0.00899
AFIX  43
H4B   2    0.769597    0.385146    0.805211    11.00000   -1.20000
AFIX   0
C5B   1    0.676331    0.530924    0.766830    11.00000    0.07313    0.09214 =
         0.05652    0.00590   -0.01216   -0.03327
AFIX  43
H5B   2    0.711106    0.587237    0.801623    11.00000   -1.20000
AFIX   0
C6B   1    0.589682    0.567762    0.712429    11.00000    0.06321    0.06001 =
         0.05491    0.00211    0.00028   -0.01711
AFIX  43
H6B   2    0.566177    0.649362    0.711024    11.00000   -1.20000
AFIX   0
C7B   1    0.444206    0.525207    0.600526    11.00000    0.03981    0.05289 =
         0.05169    0.00431    0.00589   -0.00507
O8B   4    0.419793    0.635874    0.592660    11.00000    0.05491    0.05110 =
         0.08055    0.01256   -0.00091   -0.00183
O9B   4    0.390685    0.442425    0.560107    11.00000    0.05512    0.06024 =
         0.06195    0.00085   -0.01154   -0.00581
O10B  4    0.525025    0.276561    0.615947    11.00000    0.11587    0.05488 =
         0.09601   -0.01665   -0.03781    0.01600
H10B  2    0.459953    0.327181    0.584894    11.00000    0.11980

HKLF 4




REM  al_imid-salicyl_300_fiol_a.res in Pbca
REM wR2 = 0.1418, GooF = S = 1.067, Restrained GooF = 1.067 for all data
REM R1 = 0.0524 for 1775 Fo > 4sig(Fo) and 0.0799 for all 2617 data
REM 149 parameters refined using 0 restraints

END

WGHT      0.0467      0.7304

REM Highest difference peak  0.249,  deepest hole -0.219,  1-sigma level  0.056
Q1    1   0.2366  0.6294  0.4809  11.00000  0.05    0.25
Q2    1   0.6642  0.4691  0.7852  11.00000  0.05    0.20
Q3    1   0.6125  0.5616  0.7574  11.00000  0.05    0.20
Q4    1   0.6655  0.6731  0.7896  11.00000  0.05    0.18
Q5    1   0.1434  0.6959  0.4412  11.00000  0.05    0.18
Q6    1   0.7194  0.6573  0.7613  11.00000  0.05    0.16
Q7    1   0.1920  0.5273  0.4401  11.00000  0.05    0.16
Q8    1   0.6515  0.3603  0.7594  11.00000  0.05    0.16
Q9    1   0.4081  0.3763  0.5788  11.00000  0.05    0.15
Q10   1   0.0797  0.6460  0.3984  11.00000  0.05    0.15
Q11   1   0.4527  0.7083  0.6352  11.00000  0.05    0.15
Q12   1   0.1119  0.5504  0.3902  11.00000  0.05    0.15
Q13   1   0.3945  0.4807  0.5861  11.00000  0.05    0.15
Q14   1   0.4003  0.6280  0.6082  11.00000  0.05    0.15
Q15   1   0.4577  0.6792  0.6029  11.00000  0.05    0.14
Q16   1   0.6965  0.6321  0.8161  11.00000  0.05    0.14
Q17   1   0.3619  0.6858  0.6112  11.00000  0.05    0.14
Q18   1   0.7444  0.2966  0.8114  11.00000  0.05    0.14
Q19   1   0.5040  0.1855  0.6286  11.00000  0.05    0.13
Q20   1   0.1777  0.3803  0.4519  11.00000  0.05    0.13
;
_shelx_res_checksum              97665

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: AcOEt'
####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2371023'
loop_
_audit_author_name
_audit_author_address
'Andrzej Gzella'
;Poznan University of Medical Sciences
Poland
;
_audit_update_record             
;
2024-07-15 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
Imidazolium 2-hydroxybenzoate
;
_chemical_name_common            ?
_chemical_melting_point          401-403
_chemical_formula_moiety         'C7 H5 O3^-^, C3 H5 N2^+^'
_chemical_formula_sum            'C10 H10 N2 O3'
_chemical_formula_weight         206.20

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.1043(5)
_cell_length_b                   10.9664(5)
_cell_length_c                   16.3069(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1985.76(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    180.0(1)
_cell_measurement_reflns_used    5447
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      28.56

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64014
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3991
_diffrn_reflns_number            16741
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         29.64
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2567
_reflns_number_gt                2058
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
; 
WINGX (Farrugia, 2012), OLEX2 v1.2-alpha (Dolomanov et al., 2009), 
PLATON (Spek, 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0393P)²+0.8890P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0069(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2567
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1A N 0.21025(11) 0.55465(12) 0.52359(8) 0.0369(3) Uani 1 1 d . . . . .
H1A H 0.275(2) 0.5239(19) 0.4956(13) 0.067(6) Uiso 1 1 d . . . . .
N2A N 0.07856(12) 0.68185(12) 0.56667(8) 0.0400(3) Uani 1 1 d . . . . .
H2A H 0.034(2) 0.752(2) 0.5752(14) 0.074(7) Uiso 1 1 d . . . . .
C1A C 0.17481(13) 0.66897(14) 0.51954(9) 0.0376(3) Uani 1 1 d . . . . .
H1AA H 0.211915 0.731546 0.488166 0.045 Uiso 1 1 calc R U . . .
C2A C 0.05357(16) 0.57263(17) 0.60136(10) 0.0476(4) Uani 1 1 d . . . . .
H2AA H -0.010572 0.555780 0.638203 0.057 Uiso 1 1 calc R U . . .
C3A C 0.13498(16) 0.49320(15) 0.57457(10) 0.0444(4) Uani 1 1 d . . . . .
H3AA H 0.139626 0.409207 0.588476 0.053 Uiso 1 1 calc R U . . .
C1B C 0.53892(11) 0.48468(12) 0.34041(8) 0.0288(3) Uani 1 1 d . . . . .
C2B C 0.57393(13) 0.36221(13) 0.33598(9) 0.0356(3) Uani 1 1 d . . . . .
C3B C 0.66261(15) 0.32570(16) 0.28100(10) 0.0460(4) Uani 1 1 d . . . . .
H3B H 0.686425 0.242564 0.278664 0.055 Uiso 1 1 calc R U . . .
C4B C 0.71563(14) 0.40934(17) 0.23023(10) 0.0471(4) Uani 1 1 d . . . . .
H4B H 0.776744 0.383872 0.193235 0.057 Uiso 1 1 calc R U . . .
C5B C 0.68127(15) 0.53048(16) 0.23220(9) 0.0445(4) Uani 1 1 d . . . . .
H5B H 0.717654 0.587839 0.196251 0.053 Uiso 1 1 calc R U . . .
C6B C 0.59348(13) 0.56738(14) 0.28694(9) 0.0363(3) Uani 1 1 d . . . . .
H6B H 0.569807 0.650609 0.288205 0.044 Uiso 1 1 calc R U . . .
C7B C 0.44516(12) 0.52571(12) 0.40008(8) 0.0291(3) Uani 1 1 d . . . . .
O8B O 0.42096(9) 0.63624(9) 0.40735(7) 0.0369(3) Uani 1 1 d . . . . .
O9B O 0.39104(9) 0.44290(9) 0.44130(6) 0.0347(3) Uani 1 1 d . . . . .
O10B O 0.52461(13) 0.27620(10) 0.38488(8) 0.0538(4) Uani 1 1 d . . . . .
H10B H 0.465(2) 0.324(2) 0.4156(14) 0.080(7) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1A 0.0300(6) 0.0438(7) 0.0370(7) -0.0035(5) 0.0005(5) 0.0080(5)
N2A 0.0357(7) 0.0403(7) 0.0439(7) -0.0090(6) -0.0039(6) 0.0105(5)
C1A 0.0352(7) 0.0382(8) 0.0395(8) 0.0056(6) -0.0031(6) -0.0045(6)
C2A 0.0400(9) 0.0616(11) 0.0411(9) 0.0032(8) 0.0079(7) -0.0060(7)
C3A 0.0509(9) 0.0368(8) 0.0456(9) 0.0075(7) -0.0017(7) -0.0006(7)
C1B 0.0243(6) 0.0339(7) 0.0281(7) -0.0011(5) -0.0030(5) -0.0033(5)
C2B 0.0354(7) 0.0373(8) 0.0340(7) 0.0022(6) 0.0021(6) 0.0031(6)
C3B 0.0436(9) 0.0490(9) 0.0453(9) -0.0035(7) 0.0068(7) 0.0124(7)
C4B 0.0333(8) 0.0685(11) 0.0395(9) -0.0114(8) 0.0089(6) -0.0036(7)
C5B 0.0423(9) 0.0574(10) 0.0340(8) -0.0048(7) 0.0066(7) -0.0200(7)
C6B 0.0386(8) 0.0373(8) 0.0329(7) -0.0020(6) -0.0014(6) -0.0105(6)
C7B 0.0230(6) 0.0338(7) 0.0305(7) -0.0030(5) -0.0046(5) -0.0023(5)
O8B 0.0314(5) 0.0314(5) 0.0479(6) -0.0077(4) 0.0000(4) -0.0015(4)
O9B 0.0314(5) 0.0361(5) 0.0367(5) -0.0008(4) 0.0063(4) -0.0031(4)
O10B 0.0715(9) 0.0346(6) 0.0551(8) 0.0104(5) 0.0238(6) 0.0113(6)

_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
N1A C1A 1.3156(19) . ?
N1A C3A 1.358(2) . ?
N1A H1A 0.92(2) . ?
N2A C1A 1.324(2) . ?
N2A C2A 1.353(2) . ?
N2A H2A 0.93(2) . ?
C1A H1AA 0.9500 . ?
C2A C3A 1.329(2) . ?
C2A H2AA 0.9500 . ?
C3A H3AA 0.9500 . ?
C1B C6B 1.3964(19) . ?
C1B C2B 1.400(2) . ?
C1B C7B 1.4944(19) . ?
C2B O10B 1.3511(18) . ?
C2B C3B 1.391(2) . ?
C3B C4B 1.369(2) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.383(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.382(2) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B O8B 1.2472(17) . ?
C7B O9B 1.2797(16) . ?
O10B H10B 0.98(3) . ?

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
C1A N1A C3A 108.64(13) . . ?
C1A N1A H1A 124.1(13) . . ?
C3A N1A H1A 127.3(13) . . ?
C1A N2A C2A 108.29(13) . . ?
C1A N2A H2A 127.5(14) . . ?
C2A N2A H2A 124.2(14) . . ?
N1A C1A N2A 108.30(14) . . ?
N1A C1A H1AA 125.9 . . ?
N2A C1A H1AA 125.9 . . ?
C3A C2A N2A 107.65(15) . . ?
C3A C2A H2AA 126.2 . . ?
N2A C2A H2AA 126.2 . . ?
C2A C3A N1A 107.13(14) . . ?
C2A C3A H3AA 126.4 . . ?
N1A C3A H3AA 126.4 . . ?
C6B C1B C2B 118.06(13) . . ?
C6B C1B C7B 120.88(13) . . ?
C2B C1B C7B 121.05(12) . . ?
O10B C2B C3B 117.81(14) . . ?
O10B C2B C1B 121.79(13) . . ?
C3B C2B C1B 120.40(14) . . ?
C4B C3B C2B 120.10(15) . . ?
C4B C3B H3B 119.9 . . ?
C2B C3B H3B 119.9 . . ?
C3B C4B C5B 120.75(15) . . ?
C3B C4B H4B 119.6 . . ?
C5B C4B H4B 119.6 . . ?
C6B C5B C4B 119.40(15) . . ?
C6B C5B H5B 120.3 . . ?
C4B C5B H5B 120.3 . . ?
C5B C6B C1B 121.27(15) . . ?
C5B C6B H6B 119.4 . . ?
C1B C6B H6B 119.4 . . ?
O8B C7B O9B 122.59(13) . . ?
O8B C7B C1B 120.31(12) . . ?
O9B C7B C1B 117.10(12) . . ?
C2B O10B H10B 101.6(14) . . ?

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
C3A N1A C1A N2A -0.08(18) . . . . ?
C2A N2A C1A N1A 0.26(18) . . . . ?
C1A N2A C2A C3A -0.34(19) . . . . ?
N2A C2A C3A N1A 0.29(19) . . . . ?
C1A N1A C3A C2A -0.13(19) . . . . ?
C6B C1B C2B O10B -179.25(14) . . . . ?
C7B C1B C2B O10B 0.2(2) . . . . ?
C6B C1B C2B C3B 1.5(2) . . . . ?
C7B C1B C2B C3B -179.03(13) . . . . ?
O10B C2B C3B C4B -179.85(15) . . . . ?
C1B C2B C3B C4B -0.6(2) . . . . ?
C2B C3B C4B C5B -0.7(3) . . . . ?
C3B C4B C5B C6B 0.9(2) . . . . ?
C4B C5B C6B C1B 0.1(2) . . . . ?
C2B C1B C6B C5B -1.3(2) . . . . ?
C7B C1B C6B C5B 179.26(13) . . . . ?
C6B C1B C7B O8B -5.60(19) . . . . ?
C2B C1B C7B O8B 174.94(13) . . . . ?
C6B C1B C7B O9B 173.32(12) . . . . ?
C2B C1B C7B O9B -6.14(19) . . . . ?

_refine_diff_density_max         0.364
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.052

_shelx_res_file                  
;
TITL al_imid-salicyl_180_fiol_a.res in Pbca
    shelx.res
    created by SHELXL-2018/3 at 15:27:13 on 15-Jul-2024
REM Old TITL AL_IMID-salicyl_180_fiol in Pbca
REM SHELXT solution in Pbca
REM R1 0.273, Rweak 0.123, Alpha 0.010, Orientation as input
REM Formula found by SHELXT: C10 N2 O3
CELL 0.71073 11.104294 10.966433 16.306895 90 90 90
ZERR 8 0.000545 0.00053 0.000869 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O
UNIT 80 80 16 24

L.S. 10
PLAN  20
TEMP -93
CONF
BOND $H
list 4
MORE -1
fmap 2
acta
OMIT 0 0 2
OMIT 1 0 2
OMIT 6 3 9
REM <olex2.extras>
REM <HklSrc "%.\\AL_IMID-salicyl_180_fiol.hkl">
REM </olex2.extras>

WGHT    0.039300    0.889000
EXTI    0.006866
FVAR       4.33135
N1A   3    0.210246    0.554650    0.523593    11.00000    0.03002    0.04377 =
         0.03698   -0.00347    0.00051    0.00803
H1A   2    0.274920    0.523922    0.495581    11.00000    0.06703
N2A   3    0.078563    0.681846    0.566670    11.00000    0.03570    0.04034 =
         0.04390   -0.00896   -0.00388    0.01049
H2A   2    0.033857    0.751931    0.575203    11.00000    0.07431
C1A   1    0.174806    0.668966    0.519538    11.00000    0.03524    0.03817 =
         0.03950    0.00559   -0.00307   -0.00451
AFIX  43
H1AA  2    0.211915    0.731546    0.488166    11.00000   -1.20000
AFIX   0
C2A   1    0.053573    0.572633    0.601358    11.00000    0.04003    0.06159 =
         0.04105    0.00316    0.00793   -0.00598
AFIX  43
H2AA  2   -0.010572    0.555780    0.638203    11.00000   -1.20000
AFIX   0
C3A   1    0.134978    0.493199    0.574569    11.00000    0.05093    0.03677 =
         0.04561    0.00753   -0.00169   -0.00059
AFIX  43
H3AA  2    0.139626    0.409207    0.588476    11.00000   -1.20000
AFIX   0

C1B   1    0.538925    0.484681    0.340410    11.00000    0.02434    0.03387 =
         0.02805   -0.00114   -0.00300   -0.00333
C2B   1    0.573931    0.362211    0.335983    11.00000    0.03542    0.03733 =
         0.03404    0.00219    0.00206    0.00312
C3B   1    0.662613    0.325697    0.280996    11.00000    0.04364    0.04898 =
         0.04526   -0.00347    0.00675    0.01241
AFIX  43
H3B   2    0.686425    0.242564    0.278664    11.00000   -1.20000
AFIX   0
C4B   1    0.715635    0.409340    0.230235    11.00000    0.03331    0.06855 =
         0.03949   -0.01140    0.00889   -0.00365
AFIX  43
H4B   2    0.776744    0.383872    0.193235    11.00000   -1.20000
AFIX   0
C5B   1    0.681267    0.530481    0.232197    11.00000    0.04226    0.05740 =
         0.03396   -0.00480    0.00662   -0.01995
AFIX  43
H5B   2    0.717654    0.587839    0.196251    11.00000   -1.20000
AFIX   0
C6B   1    0.593478    0.567384    0.286939    11.00000    0.03856    0.03735 =
         0.03286   -0.00197   -0.00136   -0.01049
AFIX  43
H6B   2    0.569807    0.650609    0.288205    11.00000   -1.20000
AFIX   0
C7B   1    0.445156    0.525707    0.400075    11.00000    0.02298    0.03384 =
         0.03047   -0.00305   -0.00456   -0.00231
O8B   4    0.420964    0.636236    0.407352    11.00000    0.03142    0.03145 =
         0.04786   -0.00766   -0.00004   -0.00148
O9B   4    0.391042    0.442898    0.441297    11.00000    0.03143    0.03610 =
         0.03666   -0.00077    0.00628   -0.00310
O10B  4    0.524608    0.276196    0.384877    11.00000    0.07153    0.03462 =
         0.05510    0.01042    0.02376    0.01128
H10B  2    0.464807    0.324129    0.415640    11.00000    0.08016

HKLF 4




REM  al_imid-salicyl_180_fiol_a.res in Pbca
REM wR2 = 0.1152, GooF = S = 1.077, Restrained GooF = 1.077 for all data
REM R1 = 0.0465 for 2058 Fo > 4sig(Fo) and 0.0604 for all 2567 data
REM 149 parameters refined using 0 restraints

END

WGHT      0.0393      0.8889

REM Highest difference peak  0.364,  deepest hole -0.182,  1-sigma level  0.052
Q1    1   0.2367  0.6234  0.5213  11.00000  0.05    0.36
Q2    1   0.1857  0.5199  0.5614  11.00000  0.05    0.27
Q3    1   0.1441  0.6902  0.5583  11.00000  0.05    0.26
Q4    1   0.1125  0.5448  0.6120  11.00000  0.05    0.23
Q5    1   0.6215  0.5435  0.2508  11.00000  0.05    0.23
Q6    1   0.6639  0.3619  0.2431  11.00000  0.05    0.21
Q7    1   0.5028  0.4998  0.3708  11.00000  0.05    0.20
Q8    1   0.6041  0.3360  0.2965  11.00000  0.05    0.18
Q9    1   0.0790  0.6411  0.5983  11.00000  0.05    0.18
Q10   1   0.4827  0.1781  0.3770  11.00000  0.05    0.17
Q11   1   0.0759  0.5243  0.5689  11.00000  0.05    0.17
Q12   1   0.6787  0.4688  0.2183  11.00000  0.05    0.17
Q13   1   0.5325  0.4233  0.3337  11.00000  0.05    0.16
Q14   1   0.2844  0.6929  0.5025  11.00000  0.05    0.15
Q15   1   0.6636  0.6318  0.1865  11.00000  0.05    0.15
Q16   1   0.6601  0.6738  0.2800  11.00000  0.05    0.15
Q17   1   0.1851  0.3871  0.5497  11.00000  0.05    0.14
Q18   1   0.6801  0.2981  0.2896  11.00000  0.05    0.14
Q19   1   0.5721  0.4390  0.3513  11.00000  0.05    0.14
Q20   1   0.1249  0.4540  0.5692  11.00000  0.05    0.13
;
_shelx_res_checksum              11718

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: AcOEt'
####################################################################### 
# 
# 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_095GPa
_database_code_depnum_ccdc_archive 'CCDC 2355851'
loop_
_audit_author_name
_audit_author_address
'Michalina Rusek'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-05-16 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_audit_creation_date             2024-05-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H5 O3, C3 H5 N2'
_chemical_formula_sum            'C10 H10 N2 O3'
_chemical_formula_weight         206.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N 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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4739(8)
_cell_length_b                   10.652(7)
_cell_length_c                   15.1725(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1854.4(12)
_cell_formula_units_Z            8
_cell_measurement_pressure       950000(2)
_cell_measurement_reflns_used    1207
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.7570
_cell_measurement_theta_min      4.7730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Data were collected at room temperature and pressure of 0.95(2) GPa
 (950000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0830
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.417
_diffrn_reflns_Laue_measured_fraction_max 0.387
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7603
_diffrn_reflns_point_group_measured_fraction_full 0.417
_diffrn_reflns_point_group_measured_fraction_max 0.387
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.463
_diffrn_reflns_theta_min         4.803
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.417
_diffrn_measured_fraction_theta_max 0.387
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ    -35.00  19.75   0.75   35.00   0.00 -30.00   0.00    --    73
  2  φ    140.00 200.00   0.75   35.00   0.00 -30.00   0.00    --    80
  3  φ    160.00 217.00   0.75   35.00   0.00  30.00   0.00    --    76
  4  φ    -20.00  34.75   0.75   35.00   0.00  30.00   0.00    --    73
  5  ω    -24.00  24.00   0.75   35.00    --   30.00  39.46 -12.90   64
  6  ω    -24.00  24.00   0.75   35.00    --   30.00  39.46 167.10   64
  7  ω    -50.00  10.00   0.75   35.00    --  -30.00  39.46 167.10   80
  8  ω    -50.00  10.00   0.75   35.00    --  -30.00  39.46 -12.90   80
  9  ω    -64.00  -8.50   0.75   35.00    --  -30.00  81.40 -28.90   74
 10  ω    -64.00  -8.50   0.75   35.00    --  -30.00  81.40 151.10   74
 11  ω    -19.00   8.00   0.75   35.00    --   30.00  81.40 151.10   36
 12  ω    -19.00   8.00   0.75   35.00    --   30.00  81.40 -28.90   36
 13  ω    -43.00 -21.25   0.75   35.00    --   30.00 134.60 -56.90   29
 14  ω    -43.00 -21.25   0.75   35.00    --   30.00 134.60 123.10   29
 15  ω    -90.00 -36.00   0.75   35.00    --  -30.00 134.60 123.10   72
 16  ω    -90.00 -36.00   0.75   35.00    --  -30.00 134.60 -56.90   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0103011000
_diffrn_orient_matrix_UB_12      0.0649280000
_diffrn_orient_matrix_UB_13      0.0067223000
_diffrn_orient_matrix_UB_21      -0.0050414000
_diffrn_orient_matrix_UB_22      0.0106726000
_diffrn_orient_matrix_UB_23      -0.0460151000
_diffrn_orient_matrix_UB_31      -0.0607355000
_diffrn_orient_matrix_UB_32      0.0101212000
_diffrn_orient_matrix_UB_33      0.0049627000
_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                376
_reflns_number_total             744
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         744
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      1.002
_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)+(0.0839P)²+0.5807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1688
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H3(0.081) H4(0.06) H5(0.077) H6(0.063) H3A(0.1) H1(0.059)
 H2(0.077) H8(0.077) H9(0.097) H10(0.072)
 Fixed X: H3(0.677128) H4(0.772636) H5(0.71678) H6(0.575033) H3A(0.465187)
 H1(0.27739) H2(0.03897) H8(0.214082) H9(0.145967) H10(-0.003018)
 Fixed Y: H3(0.230356) H4(0.385075) H5(0.59097) H6(0.652383) H3A(0.297563)
 H1(0.531774) H2(0.74254) H8(0.744826) H9(0.401792) H10(0.55391)
 Fixed Z: H3(0.271105) H4(0.186562) H5(0.186501) H6(0.284004) H3A(0.409919)
 H1(0.499427) H2(0.574842) H8(0.497089) H9(0.586375) H10(0.63808)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.5399(5) 0.4819(15) 0.3365(4) 0.041(2) Uani 1 1 d . U . . .
C2 C 0.5692(6) 0.3603(16) 0.3323(4) 0.049(3) Uani 1 1 d . U . . .
C3 C 0.6570(5) 0.3148(14) 0.2748(3) 0.067(2) Uani 1 1 d . U . . .
H3 H 0.677128 0.230356 0.271105 0.081 Uiso 1 1 calc R U . . .
C4 C 0.7117(5) 0.4093(17) 0.2232(4) 0.050(2) Uani 1 1 d . U . . .
H4 H 0.772636 0.385075 0.186562 0.060 Uiso 1 1 calc R U . . .
C5 C 0.6812(6) 0.5332(17) 0.2238(4) 0.064(3) Uani 1 1 d . U . . .
H5 H 0.716780 0.590970 0.186501 0.077 Uiso 1 1 calc R U . . .
C6 C 0.5964(4) 0.5683(13) 0.2812(3) 0.052(2) Uani 1 1 d . U . . .
H6 H 0.575033 0.652383 0.284004 0.063 Uiso 1 1 calc R U . . .
C7 C 0.4462(6) 0.5270(18) 0.3987(5) 0.041(3) Uani 1 1 d . U . . .
O1 O 0.4225(4) 0.6391(11) 0.4050(3) 0.056(3) Uani 1 1 d . U . . .
O2 O 0.3943(3) 0.4416(9) 0.4442(2) 0.047(3) Uani 1 1 d . U . . .
O3 O 0.5187(4) 0.2680(10) 0.3807(3) 0.084(3) Uani 1 1 d . U . . .
H3A H 0.465187 0.297563 0.409919 0.100 Uiso 1 1 calc R U . . .
N1 N 0.2158(4) 0.5588(12) 0.5255(3) 0.049(2) Uani 1 1 d . U . . .
H1 H 0.277390 0.531774 0.499427 0.059 Uiso 1 1 calc R U . . .
N2 N 0.0824(5) 0.6774(14) 0.5685(4) 0.064(3) Uani 1 1 d . U . . .
H2 H 0.038970 0.742540 0.574842 0.077 Uiso 1 1 calc R U . . .
C8 C 0.1784(6) 0.6767(17) 0.5243(4) 0.064(2) Uani 1 1 d . U . . .
H8 H 0.214082 0.744826 0.497089 0.077 Uiso 1 1 calc R U . . .
C9 C 0.1417(7) 0.4873(16) 0.5743(4) 0.081(2) Uani 1 1 d . U . . .
H9 H 0.145967 0.401792 0.586375 0.097 Uiso 1 1 calc R U . . .
C10 C 0.0597(5) 0.5717(17) 0.6013(4) 0.060(8) Uani 1 1 d . . . . .
H10 H -0.003018 0.553910 0.638080 0.072 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.040(3) 0.040(5) 0.044(3) 0.003(4) 0.000(2) 0.001(4)
C2 0.050(3) 0.050(5) 0.047(3) 0.002(4) 0.006(2) 0.001(4)
C3 0.064(3) 0.068(5) 0.070(3) -0.004(4) 0.002(3) 0.002(4)
C4 0.044(3) 0.049(5) 0.056(3) 0.000(4) 0.003(2) -0.003(4)
C5 0.062(3) 0.064(6) 0.066(3) -0.001(4) 0.010(3) -0.005(4)
C6 0.053(3) 0.051(5) 0.052(2) 0.002(3) 0.004(2) -0.005(3)
C7 0.038(3) 0.042(6) 0.044(3) 0.000(4) -0.004(2) -0.002(4)
O1 0.043(2) 0.050(10) 0.076(3) -0.006(5) -0.0059(18) -0.002(4)
O2 0.0414(19) 0.043(9) 0.0555(19) 0.006(4) 0.0071(16) -0.002(3)
O3 0.090(3) 0.082(9) 0.078(3) 0.005(4) 0.026(2) 0.011(4)
N1 0.044(2) 0.049(5) 0.056(2) -0.005(3) 0.0080(18) 0.007(3)
N2 0.063(3) 0.064(5) 0.066(3) -0.006(4) -0.003(3) 0.014(4)
C8 0.063(3) 0.064(3) 0.064(2) 0.0006(11) -0.0005(10) 0.0000(11)
C9 0.081(3) 0.081(3) 0.080(3) 0.0006(11) -0.0006(11) 0.0003(11)
C10 0.052(4) 0.08(3) 0.054(4) 0.013(6) 0.015(3) 0.007(6)

_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
C1 C2 1.340(19) . ?
C1 C6 1.403(14) . ?
C1 C7 1.510(11) . ?
C2 C3 1.419(11) . ?
C2 O3 1.357(15) . ?
C3 H3 0.9300 . ?
C3 C4 1.421(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.37(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.358(10) . ?
C6 H6 0.9300 . ?
C7 O1 1.227(19) . ?
C7 O2 1.288(17) . ?
O3 H3A 0.8200 . ?
N1 H1 0.8600 . ?
N1 C8 1.327(19) . ?
N1 C9 1.361(13) . ?
N2 H2 0.8600 . ?
N2 C8 1.289(8) . ?
N2 C10 1.26(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.364(18) . ?
C10 H10 0.9300 . ?

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
C2 C1 C6 119.3(8) . . ?
C2 C1 C7 121.1(12) . . ?
C6 C1 C7 119.6(14) . . ?
C1 C2 C3 122.5(12) . . ?
C1 C2 O3 124.6(8) . . ?
O3 C2 C3 112.9(13) . . ?
C2 C3 H3 122.9 . . ?
C2 C3 C4 114.2(13) . . ?
C4 C3 H3 122.9 . . ?
C3 C4 H4 117.7 . . ?
C5 C4 C3 124.6(8) . . ?
C5 C4 H4 117.7 . . ?
C4 C5 H5 121.5 . . ?
C6 C5 C4 116.9(11) . . ?
C6 C5 H5 121.5 . . ?
C1 C6 H6 118.9 . . ?
C5 C6 C1 122.3(13) . . ?
C5 C6 H6 118.9 . . ?
O1 C7 C1 121.0(14) . . ?
O1 C7 O2 122.9(7) . . ?
O2 C7 C1 116.0(15) . . ?
C2 O3 H3A 109.5 . . ?
C8 N1 H1 125.2 . . ?
C8 N1 C9 109.6(8) . . ?
C9 N1 H1 125.2 . . ?
C8 N2 H2 123.9 . . ?
C10 N2 H2 123.9 . . ?
C10 N2 C8 112.2(14) . . ?
N1 C8 H8 127.0 . . ?
N2 C8 N1 105.9(12) . . ?
N2 C8 H8 127.0 . . ?
N1 C9 H9 128.5 . . ?
N1 C9 C10 103.0(13) . . ?
C10 C9 H9 128.5 . . ?
N2 C10 C9 109.2(8) . . ?
N2 C10 H10 125.4 . . ?
C9 C10 H10 125.4 . . ?

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
C1 C2 C3 C4 0.7(9) . . . . ?
C2 C1 C6 C5 -0.7(10) . . . . ?
C2 C1 C7 O1 177.2(8) . . . . ?
C2 C1 C7 O2 -2.5(10) . . . . ?
C2 C3 C4 C5 -3.1(9) . . . . ?
C3 C4 C5 C6 3.5(11) . . . . ?
C4 C5 C6 C1 -1.5(10) . . . . ?
C6 C1 C2 C3 1.0(11) . . . . ?
C6 C1 C2 O3 -178.3(5) . . . . ?
C6 C1 C7 O1 -3.6(10) . . . . ?
C6 C1 C7 O2 176.7(5) . . . . ?
C7 C1 C2 C3 -179.8(5) . . . . ?
C7 C1 C2 O3 0.9(12) . . . . ?
C7 C1 C6 C5 -179.9(6) . . . . ?
O3 C2 C3 C4 -179.9(5) . . . . ?
N1 C9 C10 N2 2.4(9) . . . . ?
C8 N1 C9 C10 -0.2(8) . . . . ?
C8 N2 C10 C9 -3.8(10) . . . . ?
C9 N1 C8 N2 -1.9(8) . . . . ?
C10 N2 C8 N1 3.6(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT029_095GPa              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.417 Why?  
RESPONSE: It is due to high-pressure conditions
;
_vrf_PLAT340_095GPa              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0155 Ang.  
RESPONSE: It is due to high-pressure conditions
;
####################################################################### 
# 
# 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_13GPa
_database_code_depnum_ccdc_archive 'CCDC 2355852'
loop_
_audit_author_name
_audit_author_address
'Michalina Rusek'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-05-16 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_audit_creation_date             2024-05-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H5 O3, C3 H5 N2'
_chemical_formula_sum            'C10 H10 N2 O3'
_chemical_formula_weight         206.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N 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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5502(8)
_cell_length_b                   10.596(7)
_cell_length_c                   14.8160(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1813.3(12)
_cell_formula_units_Z            8
_cell_measurement_pressure       1300000(2)
_cell_measurement_reflns_used    1257
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.9980
_cell_measurement_theta_min      4.8410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Data were collected at room temperature and pressure of 1.30(2) GPa
 (1300000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.417
_diffrn_reflns_Laue_measured_fraction_max 0.387
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7442
_diffrn_reflns_point_group_measured_fraction_full 0.417
_diffrn_reflns_point_group_measured_fraction_max 0.387
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.523
_diffrn_reflns_theta_min         4.872
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.417
_diffrn_measured_fraction_theta_max 0.387
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ    -35.00  19.75   0.75   35.00   0.00 -30.00   0.00    --    73
  2  φ    140.00 200.00   0.75   35.00   0.00 -30.00   0.00    --    80
  3  φ    160.00 217.00   0.75   35.00   0.00  30.00   0.00    --    76
  4  φ    -20.00  34.75   0.75   35.00   0.00  30.00   0.00    --    73
  5  ω    -24.00  24.00   0.75   35.00    --   30.00  39.46 -12.90   64
  6  ω    -24.00  24.00   0.75   35.00    --   30.00  39.46 167.10   64
  7  ω    -50.00  10.00   0.75   35.00    --  -30.00  39.46 167.10   80
  8  ω    -50.00  10.00   0.75   35.00    --  -30.00  39.46 -12.90   80
  9  ω    -64.00  -8.50   0.75   35.00    --  -30.00  81.40 -28.90   74
 10  ω    -64.00  -8.50   0.75   35.00    --  -30.00  81.40 151.10   74
 11  ω    -19.00   8.00   0.75   35.00    --   30.00  81.40 151.10   36
 12  ω    -19.00   8.00   0.75   35.00    --   30.00  81.40 -28.90   36
 13  ω    -43.00 -21.25   0.75   35.00    --   30.00 134.60 -56.90   29
 14  ω    -43.00 -21.25   0.75   35.00    --   30.00 134.60 123.10   29
 15  ω    -90.00 -36.00   0.75   35.00    --  -30.00 134.60 123.10   72
 16  ω    -90.00 -36.00   0.75   35.00    --  -30.00 134.60 -56.90   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0103271000
_diffrn_orient_matrix_UB_12      0.0654560000
_diffrn_orient_matrix_UB_13      -0.0063112000
_diffrn_orient_matrix_UB_21      0.0057222000
_diffrn_orient_matrix_UB_22      0.0100122000
_diffrn_orient_matrix_UB_23      0.0471208000
_diffrn_orient_matrix_UB_31      0.0602188000
_diffrn_orient_matrix_UB_32      0.0102138000
_diffrn_orient_matrix_UB_33      -0.0055492000
_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                368
_reflns_number_total             732
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         732
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.001
_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)+(0.0710P)²+1.8095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1712
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H3(0.077) H4(0.062) H5(0.071) H6(0.061) H3A(0.099) H1(0.06)
 H2(0.081) H8(0.082) H9(0.1) H10(0.068)
 Fixed X: H3(0.676456) H4(0.772865) H5(0.722036) H6(0.578053) H3A(0.461184)
 H1(0.280025) H2(0.039704) H8(0.214439) H9(0.14637) H10(-0.005571)
 Fixed Y: H3(0.226176) H4(0.380329) H5(0.588263) H6(0.651334) H3A(0.292125)
 H1(0.536734) H2(0.745803) H8(0.744507) H9(0.396708) H10(0.543637)
 Fixed Z: H3(0.269757) H4(0.185255) H5(0.18584) H6(0.282063) H3A(0.410268)
 H1(0.502181) H2(0.579564) H8(0.498672) H9(0.583835) H10(0.634185)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.5397(5) 0.4819(17) 0.3361(4) 0.043(2) Uani 1 1 d . U . . .
C2 C 0.5672(6) 0.3583(18) 0.3315(5) 0.049(3) Uani 1 1 d . U . . .
C3 C 0.6569(5) 0.3112(15) 0.2734(4) 0.065(3) Uani 1 1 d . U . . .
H3 H 0.676456 0.226176 0.269757 0.077 Uiso 1 1 calc R U . . .
C4 C 0.7122(5) 0.4054(18) 0.2224(4) 0.051(3) Uani 1 1 d . U . . .
H4 H 0.772865 0.380329 0.185255 0.062 Uiso 1 1 calc R U . . .
C5 C 0.6843(6) 0.5305(18) 0.2228(5) 0.059(3) Uani 1 1 d . U . . .
H5 H 0.722036 0.588263 0.185840 0.071 Uiso 1 1 calc R U . . .
C6 C 0.5986(4) 0.5665(13) 0.2801(3) 0.051(2) Uani 1 1 d . U . . .
H6 H 0.578053 0.651334 0.282063 0.061 Uiso 1 1 calc R U . . .
C7 C 0.4454(6) 0.528(2) 0.3992(5) 0.039(3) Uani 1 1 d . U . . .
O1 O 0.4228(5) 0.6406(12) 0.4049(4) 0.057(3) Uani 1 1 d . U . . .
O2 O 0.3938(3) 0.4407(10) 0.4450(3) 0.051(6) Uani 1 1 d . . . . .
O3 O 0.5149(4) 0.2628(11) 0.3808(3) 0.083(7) Uani 1 1 d . . . . .
H3A H 0.461184 0.292125 0.410268 0.099 Uiso 1 1 calc R U . . .
N1 N 0.2166(5) 0.5612(13) 0.5271(3) 0.050(2) Uani 1 1 d . U . . .
H1 H 0.280025 0.536734 0.502181 0.060 Uiso 1 1 calc R U . . .
N2 N 0.0817(5) 0.6799(15) 0.5707(4) 0.068(3) Uani 1 1 d . U . . .
H2 H 0.039704 0.745803 0.579564 0.081 Uiso 1 1 calc R U . . .
C8 C 0.1785(7) 0.6762(19) 0.5264(5) 0.069(3) Uani 1 1 d . U . . .
H8 H 0.214439 0.744507 0.498672 0.082 Uiso 1 1 calc R U . . .
C9 C 0.1414(7) 0.4831(18) 0.5735(4) 0.083(3) Uani 1 1 d . U . . .
H9 H 0.146370 0.396708 0.583835 0.100 Uiso 1 1 calc R U . . .
C10 C 0.0589(6) 0.5652(19) 0.5999(5) 0.056(3) Uani 1 1 d . U . . .
H10 H -0.005571 0.543637 0.634185 0.068 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.042(3) 0.043(5) 0.043(3) 0.000(4) -0.001(2) 0.000(4)
C2 0.050(3) 0.049(6) 0.048(3) 0.000(4) -0.004(3) -0.001(4)
C3 0.061(3) 0.065(5) 0.067(3) -0.001(4) 0.005(3) 0.005(4)
C4 0.049(3) 0.051(5) 0.054(3) 0.000(4) 0.003(2) -0.003(4)
C5 0.057(3) 0.059(6) 0.061(3) 0.000(4) 0.007(3) -0.008(4)
C6 0.054(3) 0.050(5) 0.049(2) -0.002(4) 0.000(2) -0.007(3)
C7 0.038(3) 0.039(6) 0.041(3) 0.000(4) -0.006(2) -0.001(4)
O1 0.043(2) 0.057(10) 0.072(3) -0.005(5) -0.0056(19) 0.006(5)
O2 0.046(2) 0.053(19) 0.053(2) 0.005(4) 0.0046(18) -0.003(4)
O3 0.093(4) 0.08(2) 0.076(3) 0.017(5) 0.024(3) 0.014(5)
N1 0.044(2) 0.050(5) 0.055(3) -0.007(3) 0.003(2) 0.008(3)
N2 0.065(3) 0.067(5) 0.071(3) -0.004(4) -0.001(3) 0.011(4)
C8 0.066(4) 0.069(6) 0.071(4) 0.004(4) -0.006(3) 0.001(4)
C9 0.086(4) 0.083(6) 0.081(3) 0.007(4) -0.003(3) 0.004(4)
C10 0.054(3) 0.056(5) 0.059(3) 0.001(4) 0.010(3) 0.004(4)

_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
C1 C2 1.35(2) . ?
C1 C6 1.399(15) . ?
C1 C7 1.515(12) . ?
C2 C3 1.436(12) . ?
C2 O3 1.386(16) . ?
C3 H3 0.9300 . ?
C3 C4 1.405(17) . ?
C4 H4 0.9300 . ?
C4 C5 1.37(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.358(10) . ?
C6 H6 0.9300 . ?
C7 O1 1.23(2) . ?
C7 O2 1.29(2) . ?
O3 H3A 0.8200 . ?
N1 H1 0.8600 . ?
N1 C8 1.30(2) . ?
N1 C9 1.383(15) . ?
N2 H2 0.8600 . ?
N2 C8 1.298(9) . ?
N2 C10 1.32(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.348(19) . ?
C10 H10 0.9300 . ?

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
C2 C1 C6 118.5(9) . . ?
C2 C1 C7 120.7(13) . . ?
C6 C1 C7 120.7(15) . . ?
C1 C2 C3 122.5(13) . . ?
C1 C2 O3 125.4(8) . . ?
O3 C2 C3 112.1(14) . . ?
C2 C3 H3 123.1 . . ?
C4 C3 C2 113.8(13) . . ?
C4 C3 H3 123.1 . . ?
C3 C4 H4 117.3 . . ?
C5 C4 C3 125.5(9) . . ?
C5 C4 H4 117.3 . . ?
C4 C5 H5 121.7 . . ?
C6 C5 C4 116.6(12) . . ?
C6 C5 H5 121.7 . . ?
C1 C6 H6 118.5 . . ?
C5 C6 C1 123.0(13) . . ?
C5 C6 H6 118.5 . . ?
O1 C7 C1 120.4(15) . . ?
O1 C7 O2 124.2(8) . . ?
O2 C7 C1 115.4(16) . . ?
C2 O3 H3A 109.5 . . ?
C8 N1 H1 124.7 . . ?
C8 N1 C9 110.7(9) . . ?
C9 N1 H1 124.7 . . ?
C8 N2 H2 126.0 . . ?
C8 N2 C10 108.1(14) . . ?
C10 N2 H2 126.0 . . ?
N1 C8 N2 108.5(14) . . ?
N1 C8 H8 125.8 . . ?
N2 C8 H8 125.8 . . ?
N1 C9 H9 129.2 . . ?
C10 C9 N1 101.7(14) . . ?
C10 C9 H9 129.2 . . ?
N2 C10 C9 111.1(9) . . ?
N2 C10 H10 124.5 . . ?
C9 C10 H10 124.5 . . ?

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
C1 C2 C3 C4 0.0(9) . . . . ?
C2 C1 C6 C5 -1.7(10) . . . . ?
C2 C1 C7 O1 178.1(8) . . . . ?
C2 C1 C7 O2 -1.5(10) . . . . ?
C2 C3 C4 C5 -2.3(10) . . . . ?
C3 C4 C5 C6 2.5(12) . . . . ?
C4 C5 C6 C1 -0.4(10) . . . . ?
C6 C1 C2 C3 1.9(11) . . . . ?
C6 C1 C2 O3 -178.3(5) . . . . ?
C6 C1 C7 O1 -3.1(11) . . . . ?
C6 C1 C7 O2 177.2(6) . . . . ?
C7 C1 C2 C3 -179.3(5) . . . . ?
C7 C1 C2 O3 0.5(12) . . . . ?
C7 C1 C6 C5 179.5(6) . . . . ?
O3 C2 C3 C4 -179.9(5) . . . . ?
N1 C9 C10 N2 1.1(9) . . . . ?
C8 N1 C9 C10 -1.0(8) . . . . ?
C8 N2 C10 C9 -0.8(10) . . . . ?
C9 N1 C8 N2 0.6(9) . . . . ?
C10 N2 C8 N1 0.1(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT029_13GPa               
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.417 Why?  
RESPONSE: It is due to high-pressure conditions
;
_vrf_PLAT340_13GPa               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01875 Ang.  
RESPONSE: It is due to high-pressure conditions
;
####################################################################### 
# 
# 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_167GPa
_database_code_depnum_ccdc_archive 'CCDC 2355853'
loop_
_audit_author_name
_audit_author_address
'Michalina Rusek'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-05-16 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_audit_creation_date             2024-05-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H5 O3, C3 H5 N2'
_chemical_formula_sum            'C10 H10 N2 O3'
_chemical_formula_weight         206.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N 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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.562(3)
_cell_length_b                   10.656(19)
_cell_length_c                   14.409(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1775(3)
_cell_formula_units_Z            8
_cell_measurement_pressure       1670000(2)
_cell_measurement_reflns_used    612
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.5790
_cell_measurement_theta_min      4.4950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Data were collected at room temperature and pressure of 1.67(2) GPa
 (1670000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1062
_diffrn_reflns_av_unetI/netI     0.0921
_diffrn_reflns_Laue_measured_fraction_full 0.405
_diffrn_reflns_Laue_measured_fraction_max 0.374
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6634
_diffrn_reflns_point_group_measured_fraction_full 0.405
_diffrn_reflns_point_group_measured_fraction_max 0.374
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.671
_diffrn_reflns_theta_min         4.909
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.405
_diffrn_measured_fraction_theta_max 0.374
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ    -35.00  19.75   0.75   35.00   0.00 -30.00   0.00    --    73
  2  φ    140.00 200.00   0.75   35.00   0.00 -30.00   0.00    --    80
  3  φ    160.00 217.00   0.75   35.00   0.00  30.00   0.00    --    76
  4  φ    -20.00  34.75   0.75   35.00   0.00  30.00   0.00    --    73
  5  ω    -24.00  24.00   0.75   35.00    --   30.00  39.46 -12.90   64
  6  ω    -24.00  24.00   0.75   35.00    --   30.00  39.46 167.10   64
  7  ω    -50.00  10.00   0.75   35.00    --  -30.00  39.46 167.10   80
  8  ω    -50.00  10.00   0.75   35.00    --  -30.00  39.46 -12.90   80
  9  ω    -64.00  -8.50   0.75   35.00    --  -30.00  81.40 -28.90   74
 10  ω    -64.00  -8.50   0.75   35.00    --  -30.00  81.40 151.10   74
 11  ω    -19.00   8.00   0.75   35.00    --   30.00  81.40 151.10   36
 12  ω    -19.00   8.00   0.75   35.00    --   30.00  81.40 -28.90   36
 13  ω    -43.00 -21.25   0.75   35.00    --   30.00 134.60 -56.90   29
 14  ω    -43.00 -21.25   0.75   35.00    --   30.00 134.60 123.10   29
 15  ω    -90.00 -36.00   0.75   35.00    --  -30.00 134.60 123.10   72
 16  ω    -90.00 -36.00   0.75   35.00    --  -30.00 134.60 -56.90   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0094479000
_diffrn_orient_matrix_UB_12      -0.0654038000
_diffrn_orient_matrix_UB_13      -0.0093845000
_diffrn_orient_matrix_UB_21      -0.0028220000
_diffrn_orient_matrix_UB_22      -0.0131157000
_diffrn_orient_matrix_UB_23      0.0479132000
_diffrn_orient_matrix_UB_31      -0.0601495000
_diffrn_orient_matrix_UB_32      -0.0094222000
_diffrn_orient_matrix_UB_33      -0.0038456000
_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                229
_reflns_number_total             702
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         702
_refine_ls_number_restraints     90
_refine_ls_R_factor_all          0.2221
_refine_ls_R_factor_gt           0.0743
_refine_ls_restrained_S_all      0.979
_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)+(0.1461P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1963
_refine_ls_wR_factor_ref         0.2991
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H3(0.114) H4(0.094) H5(0.118) H6(0.1) H3A(0.134) H1(0.1)
 H2(0.128) H8(0.123) H9(0.158) H10(0.112)
 Fixed X: H3(0.674736) H4(0.775174) H5(0.725641) H6(0.580739) H3A(0.44836)
 H1(0.281876) H2(0.042594) H8(0.21647) H9(0.140372) H10(-0.010287)
 Fixed Y: H3(0.220829) H4(0.37316) H5(0.590895) H6(0.651395) H3A(0.287501)
 H1(0.537954) H2(0.746324) H8(0.743908) H9(0.392074) H10(0.541835)
 Fixed Z: H3(0.268267) H4(0.185201) H5(0.184002) H6(0.28578) H3A(0.396962)
 H1(0.505813) H2(0.583265) H8(0.500539) H9(0.58111) H10(0.632325)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.5404(10) 0.473(3) 0.3350(7) 0.068(4) Uani 1 1 d . U . . .
C2 C 0.5678(13) 0.350(3) 0.3296(10) 0.098(6) Uani 1 1 d . U . . .
C3 C 0.6558(9) 0.305(3) 0.2726(7) 0.095(4) Uani 1 1 d . U . . .
H3 H 0.674736 0.220829 0.268267 0.114 Uiso 1 1 calc R U . . .
C4 C 0.7136(10) 0.399(3) 0.2221(7) 0.079(4) Uani 1 1 d . U . . .
H4 H 0.775174 0.373160 0.185201 0.094 Uiso 1 1 calc R U . . .
C5 C 0.6869(11) 0.534(3) 0.2215(8) 0.098(5) Uani 1 1 d . U . . .
H5 H 0.725641 0.590895 0.184002 0.118 Uiso 1 1 calc R U . . .
C6 C 0.6012(9) 0.567(2) 0.2802(6) 0.083(4) Uani 1 1 d . U . . .
H6 H 0.580739 0.651395 0.285780 0.100 Uiso 1 1 calc R U . . .
C7 C 0.4475(11) 0.521(3) 0.3995(9) 0.069(5) Uani 1 1 d . U . . .
O1 O 0.4216(7) 0.6415(18) 0.4042(5) 0.095(5) Uani 1 1 d . U . . .
O2 O 0.3932(6) 0.4420(16) 0.4459(4) 0.085(4) Uani 1 1 d . U . . .
O3 O 0.5105(7) 0.2596(18) 0.3789(6) 0.112(4) Uani 1 1 d . U . . .
H3A H 0.448360 0.287501 0.396962 0.134 Uiso 1 1 calc R U . . .
N1 N 0.2168(9) 0.561(2) 0.5291(6) 0.083(4) Uani 1 1 d . U . . .
H1 H 0.281876 0.537954 0.505813 0.100 Uiso 1 1 calc R U . . .
N2 N 0.0830(10) 0.680(3) 0.5727(7) 0.107(5) Uani 1 1 d . U . . .
H2 H 0.042594 0.746324 0.583265 0.128 Uiso 1 1 calc R U . . .
C8 C 0.1796(13) 0.676(3) 0.5284(8) 0.102(6) Uani 1 1 d . U . . .
H8 H 0.216470 0.743908 0.500539 0.123 Uiso 1 1 calc R U . . .
C9 C 0.1374(15) 0.479(3) 0.5730(9) 0.131(6) Uani 1 1 d . U . . .
H9 H 0.140372 0.392074 0.581110 0.158 Uiso 1 1 calc R U . . .
C10 C 0.0562(12) 0.563(3) 0.5995(9) 0.093(5) Uani 1 1 d . U . . .
H10 H -0.010287 0.541835 0.632325 0.112 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.075(5) 0.068(6) 0.061(4) -0.003(4) -0.001(3) 0.002(4)
C2 0.102(6) 0.099(8) 0.094(6) 0.002(4) -0.003(4) 0.001(4)
C3 0.097(5) 0.095(6) 0.094(5) -0.005(4) -0.003(4) -0.001(4)
C4 0.083(5) 0.079(6) 0.074(5) -0.002(4) -0.003(3) 0.001(4)
C5 0.100(6) 0.099(7) 0.096(6) 0.000(4) -0.004(4) 0.000(4)
C6 0.089(4) 0.083(6) 0.078(4) -0.003(4) -0.001(4) -0.002(4)
C7 0.075(5) 0.069(7) 0.065(5) -0.003(4) -0.002(3) -0.002(4)
O1 0.095(5) 0.095(11) 0.094(5) -0.005(7) -0.012(3) 0.011(7)
O2 0.092(4) 0.089(10) 0.072(4) -0.004(5) 0.002(3) -0.002(6)
O3 0.116(5) 0.111(10) 0.108(5) 0.002(7) 0.016(4) 0.004(7)
N1 0.085(4) 0.084(6) 0.081(4) -0.001(4) 0.004(3) 0.002(4)
N2 0.111(5) 0.107(7) 0.102(5) -0.004(4) 0.002(4) 0.003(4)
C8 0.103(6) 0.102(7) 0.102(6) 0.006(4) -0.002(4) 0.001(4)
C9 0.133(7) 0.131(8) 0.130(6) 0.005(4) 0.003(4) 0.000(4)
C10 0.094(6) 0.093(7) 0.093(5) 0.000(4) 0.004(4) -0.001(4)

_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
C1 C2 1.35(4) . ?
C1 C6 1.46(3) . ?
C1 C7 1.51(2) . ?
C2 C3 1.39(2) . ?
C2 O3 1.37(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.40(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.47(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.351(17) . ?
C6 H6 0.9300 . ?
C7 O1 1.32(3) . ?
C7 O2 1.25(3) . ?
O3 H3A 0.8200 . ?
N1 H1 0.8600 . ?
N1 C8 1.30(3) . ?
N1 C9 1.42(3) . ?
N2 H2 0.8600 . ?
N2 C8 1.288(14) . ?
N2 C10 1.35(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.35(3) . ?
C10 H10 0.9300 . ?

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
C2 C1 C6 121.7(15) . . ?
C2 C1 C7 122(2) . . ?
C6 C1 C7 116(2) . . ?
C1 C2 C3 122(2) . . ?
C1 C2 O3 122.7(17) . . ?
O3 C2 C3 115(2) . . ?
C2 C3 H3 122.8 . . ?
C2 C3 C4 114(2) . . ?
C4 C3 H3 122.8 . . ?
C3 C4 H4 116.7 . . ?
C3 C4 C5 126.7(16) . . ?
C5 C4 H4 116.7 . . ?
C4 C5 H5 122.9 . . ?
C6 C5 C4 114.3(19) . . ?
C6 C5 H5 122.9 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120(2) . . ?
C5 C6 H6 119.8 . . ?
O1 C7 C1 122(2) . . ?
O2 C7 C1 117(3) . . ?
O2 C7 O1 121.1(13) . . ?
C2 O3 H3A 109.5 . . ?
C8 N1 H1 124.0 . . ?
C8 N1 C9 112.0(15) . . ?
C9 N1 H1 124.0 . . ?
C8 N2 H2 125.9 . . ?
C8 N2 C10 108(2) . . ?
C10 N2 H2 125.9 . . ?
N1 C8 H8 125.8 . . ?
N2 C8 N1 108(2) . . ?
N2 C8 H8 125.8 . . ?
N1 C9 H9 130.3 . . ?
C10 C9 N1 99(2) . . ?
C10 C9 H9 130.3 . . ?
N2 C10 C9 112.0(16) . . ?
N2 C10 H10 124.0 . . ?
C9 C10 H10 124.0 . . ?

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
C1 C2 C3 C4 0.5(17) . . . . ?
C2 C1 C6 C5 0.5(17) . . . . ?
C2 C1 C7 O1 179.9(13) . . . . ?
C2 C1 C7 O2 -2.5(18) . . . . ?
C2 C3 C4 C5 -2.7(16) . . . . ?
C3 C4 C5 C6 3.6(17) . . . . ?
C4 C5 C6 C1 -2.3(15) . . . . ?
C6 C1 C2 C3 1(2) . . . . ?
C6 C1 C2 O3 -178.7(8) . . . . ?
C6 C1 C7 O1 1.3(17) . . . . ?
C6 C1 C7 O2 179.0(9) . . . . ?
C7 C1 C2 C3 -177.9(9) . . . . ?
C7 C1 C2 O3 3(2) . . . . ?
C7 C1 C6 C5 179.0(9) . . . . ?
O3 C2 C3 C4 179.7(9) . . . . ?
N1 C9 C10 N2 1.3(15) . . . . ?
C8 N1 C9 C10 -2.7(15) . . . . ?
C8 N2 C10 C9 0.5(16) . . . . ?
C9 N1 C8 N2 3.2(16) . . . . ?
C10 N2 C8 N1 -2.3(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT026_167GPa              
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        33% Check 
RESPONSE: It is due to high-pressure conditions
;
# start Validation Reply Form
_vrf_PLAT029_167GPa              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.405 Why?  
RESPONSE: It is due to high-pressure conditions
;
_vrf_PLAT340_167GPa              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0285 Ang.  
RESPONSE: It is due to high-pressure conditions
;
