# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_ljy-122
_database_code_depnum_ccdc_archive 'CCDC 2340776'
loop_
_audit_author_name
_audit_author_address
Yang
;luoyang normal university
China
;
_audit_update_record             
;
2024-03-16 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_audit_creation_date             2019-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H5 O6, C12 H9 N2'
_chemical_formula_sum            'C20 H14 N2 O6'
_chemical_formula_weight         378.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0499(8)
_cell_length_b                   9.5985(10)
_cell_length_c                   11.2088(11)
_cell_angle_alpha                64.656(10)
_cell_angle_beta                 78.043(8)
_cell_angle_gamma                66.903(9)
_cell_volume                     808.51(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1822
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1370
_cell_measurement_theta_min      3.8390
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5919
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         3.244
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  22.00   1.00    8.00    --  -13.49 -99.00  30.00   29
  2  ω     -1.00  69.00   1.00    8.00    --   14.89  57.00  30.00   70
  3  ω     35.00  70.00   1.00    8.00    --   14.89 178.00 150.00   35
  4  ω     50.00  80.00   1.00    8.00    --   14.89  57.00 -60.00   30
  5  ω     -2.00  81.00   1.00    8.00    --   14.89  57.00 -90.00   83
  6  ω    -46.00  42.00   1.00    8.00    --   14.89 -77.00 150.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0272763000
_diffrn_orient_matrix_UB_12      -0.0588842000
_diffrn_orient_matrix_UB_13      -0.0292146000
_diffrn_orient_matrix_UB_21      -0.0644479000
_diffrn_orient_matrix_UB_22      0.0473642000
_diffrn_orient_matrix_UB_23      -0.0433365000
_diffrn_orient_matrix_UB_31      0.0487731000
_diffrn_orient_matrix_UB_32      0.0432298000
_diffrn_orient_matrix_UB_33      -0.0467140000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2218
_reflns_number_total             3337
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0594
_refine_ls_restrained_S_all      1.058
_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)+(0.0509P)²+0.3188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1503
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5A), N2(H2), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5889(2) 0.0741(2) 0.12792(18) 0.0395(5) Uani 1 1 d . . . . .
O2 O 0.3462(2) 0.1716(2) 0.21483(19) 0.0430(5) Uani 1 1 d . . . . .
O3 O 0.5399(2) 0.8142(2) 0.19210(19) 0.0440(5) Uani 1 1 d . . . . .
H3 H 0.5593 0.8994 0.1662 0.066 Uiso 1 1 calc GR . . . .
O4 O 0.7788(2) 0.7307(2) 0.09249(19) 0.0449(5) Uani 1 1 d . . . . .
O5 O 0.8597(2) 0.4662(2) 0.04073(19) 0.0428(5) Uani 1 1 d . . . . .
H5 H 0.8769 0.5405 0.0471 0.064 Uiso 1 1 calc GR . . . .
O6 O 0.2749(2) 0.4193(2) 0.2815(2) 0.0498(6) Uani 1 1 d . . . . .
H6 H 0.2582 0.3454 0.2742 0.075 Uiso 1 1 calc GR . . . .
C1 C 0.5247(3) 0.3162(3) 0.1648(2) 0.0222(5) Uani 1 1 d . . . . .
C2 C 0.6703(3) 0.3342(3) 0.1058(2) 0.0247(5) Uani 1 1 d . . . . .
H2A H 0.7399 0.2600 0.0691 0.030 Uiso 1 1 calc R . . . .
C3 C 0.7152(3) 0.4595(3) 0.0999(2) 0.0246(5) Uani 1 1 d . . . . .
C4 C 0.6092(3) 0.5731(3) 0.1535(2) 0.0254(5) Uani 1 1 d . . . . .
C5 C 0.4637(3) 0.5545(3) 0.2132(2) 0.0275(5) Uani 1 1 d . . . . .
H5A H 0.3939 0.6291 0.2495 0.033 Uiso 1 1 calc R . . . .
C6 C 0.4196(3) 0.4289(3) 0.2204(2) 0.0275(5) Uani 1 1 d . . . . .
C7 C 0.4822(3) 0.1783(3) 0.1690(2) 0.0275(5) Uani 1 1 d . . . . .
C8 C 0.6503(3) 0.7131(3) 0.1437(2) 0.0300(6) Uani 1 1 d . . . . .
N1 N -0.0122(3) 0.2901(3) 0.3398(2) 0.0356(5) Uani 1 1 d . . . . .
N2 N 0.0968(3) 0.0706(2) 0.21739(19) 0.0329(5) Uani 1 1 d . . . . .
H2 H 0.1471 0.1348 0.2074 0.040 Uiso 1 1 calc R . . . .
C9 C -0.0721(4) 0.3987(3) 0.3960(3) 0.0436(7) Uani 1 1 d . . . . .
H9 H -0.0193 0.4719 0.3781 0.052 Uiso 1 1 calc R . . . .
C10 C -0.2097(4) 0.4101(4) 0.4806(3) 0.0492(8) Uani 1 1 d . . . . .
H10 H -0.2465 0.4884 0.5178 0.059 Uiso 1 1 calc R . . . .
C11 C -0.2888(4) 0.3046(4) 0.5075(3) 0.0463(8) Uani 1 1 d . . . . .
H11 H -0.3806 0.3104 0.5635 0.056 Uiso 1 1 calc R . . . .
C12 C -0.2314(3) 0.1862(3) 0.4505(2) 0.0363(6) Uani 1 1 d . . . . .
C13 C -0.3062(3) 0.0706(3) 0.4743(3) 0.0432(7) Uani 1 1 d . . . . .
H13 H -0.3950 0.0683 0.5332 0.052 Uiso 1 1 calc R . . . .
C14 C -0.2508(3) -0.0354(3) 0.4131(3) 0.0427(7) Uani 1 1 d . . . . .
H14 H -0.3017 -0.1100 0.4305 0.051 Uiso 1 1 calc R . . . .
C15 C -0.1149(3) -0.0350(3) 0.3218(2) 0.0333(6) Uani 1 1 d . . . . .
C16 C -0.0586(3) -0.1352(3) 0.2490(3) 0.0404(7) Uani 1 1 d . . . . .
H16 H -0.1113 -0.2058 0.2589 0.048 Uiso 1 1 calc R . . . .
C17 C 0.0727(4) -0.1304(3) 0.1636(3) 0.0436(7) Uani 1 1 d . . . . .
H17 H 0.1088 -0.1967 0.1152 0.052 Uiso 1 1 calc R . . . .
C18 C 0.1516(3) -0.0263(3) 0.1495(2) 0.0399(7) Uani 1 1 d . . . . .
H18 H 0.2425 -0.0239 0.0930 0.048 Uiso 1 1 calc R . . . .
C19 C -0.0352(3) 0.0722(3) 0.3019(2) 0.0282(6) Uani 1 1 d . . . . .
C20 C -0.0923(3) 0.1872(3) 0.3661(2) 0.0301(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.264(3) . ?
O2 C7 1.247(3) . ?
O3 H3 0.8200 . ?
O3 C8 1.304(3) . ?
O4 C8 1.227(3) . ?
O5 H5 0.8200 . ?
O5 C3 1.351(3) . ?
O6 H6 0.8200 . ?
O6 C6 1.364(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.409(3) . ?
C1 C7 1.497(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.385(3) . ?
C3 C4 1.404(3) . ?
C4 C5 1.389(3) . ?
C4 C8 1.485(3) . ?
C5 H5A 0.9300 . ?
C5 C6 1.378(3) . ?
N1 C9 1.325(3) . ?
N1 C20 1.345(3) . ?
N2 H2 0.8600 . ?
N2 C18 1.333(3) . ?
N2 C19 1.361(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.398(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.358(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.411(4) . ?
C12 C13 1.421(4) . ?
C12 C20 1.410(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.347(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.427(4) . ?
C15 C16 1.403(4) . ?
C15 C19 1.396(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.365(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.444(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
C8 O3 H3 109.5 . . ?
C3 O5 H5 109.5 . . ?
C6 O6 H6 109.5 . . ?
C2 C1 C6 118.9(2) . . ?
C2 C1 C7 119.83(19) . . ?
C6 C1 C7 121.3(2) . . ?
C1 C2 H2A 119.0 . . ?
C3 C2 C1 122.0(2) . . ?
C3 C2 H2A 119.0 . . ?
O5 C3 C2 117.46(19) . . ?
O5 C3 C4 123.5(2) . . ?
C2 C3 C4 119.0(2) . . ?
C3 C4 C8 120.5(2) . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 C8 120.5(2) . . ?
C4 C5 H5A 119.0 . . ?
C6 C5 C4 122.0(2) . . ?
C6 C5 H5A 119.0 . . ?
O6 C6 C1 122.7(2) . . ?
O6 C6 C5 118.1(2) . . ?
C5 C6 C1 119.1(2) . . ?
O1 C7 C1 117.3(2) . . ?
O2 C7 O1 124.3(2) . . ?
O2 C7 C1 118.4(2) . . ?
O3 C8 C4 115.0(2) . . ?
O4 C8 O3 123.5(2) . . ?
O4 C8 C4 121.5(2) . . ?
C9 N1 C20 116.7(2) . . ?
C18 N2 H2 118.6 . . ?
C18 N2 C19 122.9(2) . . ?
C19 N2 H2 118.6 . . ?
N1 C9 H9 118.0 . . ?
N1 C9 C10 124.0(3) . . ?
C10 C9 H9 118.0 . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.8(3) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 123.5(2) . . ?
C20 C12 C11 116.1(3) . . ?
C20 C12 C13 120.4(2) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 120.9(3) . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 123.3(3) . . ?
C19 C15 C14 118.7(2) . . ?
C19 C15 C16 118.0(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.8(3) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.6(2) . . ?
C18 C17 H17 120.2 . . ?
N2 C18 C17 119.7(2) . . ?
N2 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
N2 C19 C15 119.1(2) . . ?
N2 C19 C20 119.5(2) . . ?
C15 C19 C20 121.4(2) . . ?
N1 C20 C12 124.4(2) . . ?
N1 C20 C19 118.3(2) . . ?
C12 C20 C19 117.3(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.277
_oxdiff_exptl_absorpt_empirical_full_min 0.782
