# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

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

data_shida_5
_database_code_depnum_ccdc_archive 'CCDC 2041062'
_audit_update_record             
;
2020-10-28 deposited with the CCDC.	2022-07-21 downloaded from the CCDC.
;
_audit_creation_date             2020-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C7 H3 N O2)'
_chemical_formula_sum            'C14 H6 N2 O4'
_chemical_formula_weight         266.21
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.6356(5)
_cell_length_b                   8.2211(5)
_cell_length_c                   9.0033(7)
_cell_angle_alpha                90.202(6)
_cell_angle_beta                 107.895(6)
_cell_angle_gamma                100.224(5)
_cell_volume                     528.27(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1467
_cell_measurement_temperature    294.26(10)
_cell_measurement_theta_max      69.3910
_cell_measurement_theta_min      8.1180
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    1.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3178
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.671
_diffrn_reflns_theta_min         5.172
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.26(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    132.00 164.00   1.00    1.50    --  108.00 111.00 -30.00   32
  2  ω    105.00 131.00   1.00    1.50    --  108.00 111.00 -30.00   26
  3  ω     84.00 162.00   1.00    1.50    --  108.00  77.00 -90.00   78
  4  ω    116.00 142.00   1.00    1.50    --  108.00 111.00-180.00   26
  5  ω    147.00 173.00   1.00    1.50    --  108.00 111.00-180.00   26
  6  ω     84.00 176.00   1.00    1.50    --  108.00  25.00-120.00   92
  7  ω    102.00 152.00   1.00    1.50    --  108.00 111.00  90.00   50
  8  ω    122.00 178.00   1.00    1.50    --  108.00 111.00 120.00   56
  9  ω     93.00 173.00   1.00    1.50    --  108.00  63.00 150.00   80
 10  ω     90.00 134.00   1.00    1.50    --  108.00 -38.00 120.00   44
 11  ω     71.00 103.00   1.00    1.50    --  108.00-106.00  94.00   32
 12  ω     42.00 146.00   1.00    1.50    --  108.00 -91.00 150.00  104
 13  ω     52.00 114.00   1.00    1.50    --  108.00-111.00 -30.00   62
 14  ω     38.00 126.00   1.00    1.50    --  108.00 -50.00   0.00   88
 15  ω     42.00  67.00   1.00    1.50    --  108.00 -38.00 120.00   25
 16  ω     21.00 127.00   1.00    1.50    --   54.00  19.00 120.00  106
 17  ω     39.00  69.00   1.00    1.00    --    0.00  57.00 150.00   30
 18  ω    -17.00  14.00   1.00    1.00    --    0.00  57.00 150.00   31
 19  ω     -4.00  73.00   1.00    1.50    --   54.00 -57.00 -60.00   77
 20  ω     25.00 107.00   1.00    1.50    --   54.00-125.00-180.00   82
 21  ω      9.00  69.00   1.00    1.50    --   54.00 -57.00-150.00   60
 22  ω     28.00 113.00   1.00    1.50    --   54.00  38.00-150.00   85
 23  ω     -2.00  32.00   1.00    1.00    --    0.00  57.00 -90.00   34
 24  ω     30.00  55.00   1.00    1.50    --   54.00-125.00 120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0520787000
_diffrn_orient_matrix_UB_12      0.0733662000
_diffrn_orient_matrix_UB_13      -0.1413739000
_diffrn_orient_matrix_UB_21      0.2061651000
_diffrn_orient_matrix_UB_22      0.0493640000
_diffrn_orient_matrix_UB_23      0.1026378000
_diffrn_orient_matrix_UB_31      0.0370892000
_diffrn_orient_matrix_UB_32      -0.1690510000
_diffrn_orient_matrix_UB_33      -0.0439887000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1653
_reflns_number_total             1930
_reflns_odcompleteness_completeness 99.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1930
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.073
_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)+(0.0714P)²+0.0719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1170
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), N2(H2), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.31890(16) 0.98169(13) 1.08288(15) 0.0485(3) Uani 1 1 d . . . . .
O2 O 0.45387(15) 0.57552(14) 0.82185(13) 0.0437(3) Uani 1 1 d . . . . .
N1 N 0.38297(17) 0.77311(15) 0.95577(15) 0.0376(3) Uani 1 1 d . . . . .
H1 H 0.478611 0.840051 0.946255 0.045 Uiso 1 1 calc R . . . .
C1 C 0.2776(2) 0.83798(17) 1.03223(18) 0.0354(4) Uani 1 1 d . . . . .
C2 C 0.11236(19) 0.72208(17) 1.04815(16) 0.0309(3) Uani 1 1 d . . . . .
C3 C 0.07838(19) 0.55537(17) 0.99093(16) 0.0287(3) Uani 1 1 d . . . . .
C4 C 0.19350(18) 0.49534(17) 0.91582(16) 0.0303(3) Uani 1 1 d . . . . .
C5 C 0.35372(19) 0.61375(18) 0.89260(17) 0.0327(3) Uani 1 1 d . . . . .
C6 C -0.0039(2) 0.77724(18) 1.11787(18) 0.0356(4) Uani 1 1 d . . . . .
H6 H 0.018583 0.888016 1.152344 0.043 Uiso 1 1 calc R . . . .
C7 C -0.1577(2) 0.66689(18) 1.13764(18) 0.0346(4) Uani 1 1 d . . . . .
H7 H -0.234834 0.704370 1.187079 0.042 Uiso 1 1 calc R . . . .
O3 O 0.12040(17) 0.99362(13) 0.67803(15) 0.0497(3) Uani 1 1 d . . . . .
O4 O 0.47026(16) 0.79324(13) 0.42456(15) 0.0477(3) Uani 1 1 d . . . . .
N2 N 0.28992(17) 0.88782(14) 0.54993(16) 0.0385(3) Uani 1 1 d . . . . .
H2 H 0.361611 0.983477 0.562324 0.046 Uiso 1 1 calc R . . . .
C8 C 0.1416(2) 0.87553(17) 0.60913(18) 0.0349(4) Uani 1 1 d . . . . .
C9 C 0.01640(19) 0.71086(17) 0.58477(16) 0.0300(3) Uani 1 1 d . . . . .
C10 C 0.05847(19) 0.57883(17) 0.50991(16) 0.0280(3) Uani 1 1 d . . . . .
C11 C 0.21494(19) 0.59897(16) 0.45421(16) 0.0300(3) Uani 1 1 d . . . . .
C12 C 0.3364(2) 0.76500(17) 0.47344(18) 0.0347(4) Uani 1 1 d . . . . .
C13 C -0.1382(2) 0.68779(18) 0.63674(18) 0.0342(3) Uani 1 1 d . . . . .
H13 H -0.165657 0.776223 0.684543 0.041 Uiso 1 1 calc R . . . .
C14 C -0.2537(2) 0.53150(18) 0.61755(18) 0.0337(3) Uani 1 1 d . . . . .
H14 H -0.356948 0.516125 0.653581 0.040 Uiso 1 1 calc R . . . .


_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 C1 1.2161(18) . ?
O2 C5 1.2134(17) . ?
N1 C1 1.3769(18) . ?
N1 C5 1.3793(19) . ?
C1 C2 1.4851(19) . ?
C2 C3 1.413(2) . ?
C2 C6 1.368(2) . ?
C3 C3 1.422(3) 2_567 ?
C3 C4 1.4108(19) . ?
C4 C5 1.4913(19) . ?
C4 C7 1.368(2) 2_567 ?
C6 C7 1.409(2) . ?
O3 C8 1.2113(18) . ?
O4 C12 1.2189(18) . ?
N2 C8 1.3808(19) . ?
N2 C12 1.3755(18) . ?
C8 C9 1.485(2) . ?
C9 C10 1.410(2) . ?
C9 C13 1.382(2) . ?
C10 C10 1.414(3) 2_566 ?
C10 C11 1.4159(19) . ?
C11 C12 1.4843(19) . ?
C11 C14 1.371(2) 2_566 ?
C13 C14 1.400(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
C1 N1 C5 127.86(12) . . ?
O1 C1 N1 121.36(13) . . ?
O1 C1 C2 122.73(13) . . ?
N1 C1 C2 115.91(12) . . ?
C3 C2 C1 119.05(13) . . ?
C6 C2 C1 119.94(13) . . ?
C6 C2 C3 121.01(13) . . ?
C2 C3 C3 118.65(16) . 2_567 ?
C4 C3 C2 122.41(13) . . ?
C4 C3 C3 118.94(16) . 2_567 ?
C3 C4 C5 118.51(13) . . ?
C7 C4 C3 121.09(13) 2_567 . ?
C7 C4 C5 120.38(13) 2_567 . ?
O2 C5 N1 120.72(13) . . ?
O2 C5 C4 123.14(14) . . ?
N1 C5 C4 116.14(12) . . ?
C2 C6 C7 120.25(13) . . ?
C4 C7 C6 120.04(13) 2_567 . ?
C12 N2 C8 127.61(12) . . ?
O3 C8 N2 120.51(13) . . ?
O3 C8 C9 123.56(14) . . ?
N2 C8 C9 115.92(12) . . ?
C10 C9 C8 119.24(13) . . ?
C13 C9 C8 120.05(13) . . ?
C13 C9 C10 120.71(13) . . ?
C9 C10 C10 119.16(16) . 2_566 ?
C9 C10 C11 122.02(13) . . ?
C10 C10 C11 118.82(16) 2_566 . ?
C10 C11 C12 118.78(13) . . ?
C14 C11 C10 121.00(13) 2_566 . ?
C14 C11 C12 120.22(13) 2_566 . ?
O4 C12 N2 120.98(13) . . ?
O4 C12 C11 122.64(13) . . ?
N2 C12 C11 116.37(12) . . ?
C9 C13 C14 120.12(14) . . ?
C11 C14 C13 120.19(13) 2_566 . ?

_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 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.806
