# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_zhangyy_0507
_database_code_depnum_ccdc_archive 'CCDC 1839884'
loop_
_audit_author_name
_audit_author_address
'Zhong-Quan Liu'
;Nanjing University of Chinese Medicine
China
;
_audit_update_record             
;
2023-07-11 deposited with the CCDC.	2023-10-17 downloaded from the CCDC.
;
_audit_creation_date             2017-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 N2 O4'
_chemical_formula_sum            'C12 H10 N2 O4'
_chemical_formula_weight         246.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5350(6)
_cell_length_b                   14.4032(11)
_cell_length_c                   10.8824(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.888(7)
_cell_angle_gamma                90
_cell_volume                     1155.71(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    661
_cell_measurement_temperature    292.61(10)
_cell_measurement_theta_max      22.1570
_cell_measurement_theta_min      3.8240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3963
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.334
_diffrn_ambient_temperature      292.61(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -63.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega    9.00   67.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000  -30.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega  -33.00   82.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000  -30.0000 77
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0817822000
_diffrn_orient_matrix_UB_12      0.0193000000
_diffrn_orient_matrix_UB_13      0.0111440000
_diffrn_orient_matrix_UB_21      -0.0358220000
_diffrn_orient_matrix_UB_22      -0.0453035000
_diffrn_orient_matrix_UB_23      0.0031068000
_diffrn_orient_matrix_UB_31      0.0357553000
_diffrn_orient_matrix_UB_32      -0.0011397000
_diffrn_orient_matrix_UB_33      0.0656024000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1280
_reflns_number_total             2271
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.201
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0647
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0612P)²+0.3620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1772
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12)
;
_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 0.0537(4) 0.14518(18) 0.2690(2) 0.0728(8) Uani 1 1 d . . . . .
O2 O 0.2867(3) 0.13235(17) -0.08583(19) 0.0625(7) Uani 1 1 d . . . . .
O3 O 0.2651(5) 0.60305(19) 0.0344(2) 0.0999(11) Uani 1 1 d . . . . .
O4 O 0.4159(4) 0.62860(19) 0.2193(3) 0.0978(10) Uani 1 1 d . . . . .
N1 N 0.1685(3) 0.16270(17) 0.0889(2) 0.0463(6) Uani 1 1 d . . . . .
N2 N 0.3458(4) 0.5761(2) 0.1360(3) 0.0632(8) Uani 1 1 d . . . . .
C1 C 0.1206(4) 0.1126(2) 0.1863(3) 0.0494(8) Uani 1 1 d . . . . .
C2 C 0.1653(4) 0.0142(2) 0.1654(3) 0.0470(8) Uani 1 1 d . . . . .
C3 C 0.1450(5) -0.0646(2) 0.2323(3) 0.0579(9) Uani 1 1 d . . . . .
H3 H 0.0959 -0.0619 0.3039 0.069 Uiso 1 1 calc R . . . .
C4 C 0.1999(5) -0.1481(2) 0.1894(3) 0.0639(10) Uani 1 1 d . . . . .
H4 H 0.1891 -0.2023 0.2337 0.077 Uiso 1 1 calc R . . . .
C5 C 0.2702(5) -0.1525(2) 0.0825(3) 0.0634(10) Uani 1 1 d . . . . .
H5 H 0.3052 -0.2096 0.0554 0.076 Uiso 1 1 calc R . . . .
C6 C 0.2894(4) -0.0731(2) 0.0147(3) 0.0552(9) Uani 1 1 d . . . . .
H6 H 0.3373 -0.0758 -0.0574 0.066 Uiso 1 1 calc R . . . .
C7 C 0.2354(4) 0.0097(2) 0.0577(3) 0.0442(7) Uani 1 1 d . . . . .
C8 C 0.2376(4) 0.1054(2) 0.0070(3) 0.0467(7) Uani 1 1 d . . . . .
C9 C 0.1469(4) 0.2625(2) 0.0721(3) 0.0558(9) Uani 1 1 d . . . . .
H9A H 0.0643 0.2852 0.1229 0.067 Uiso 1 1 calc R . . . .
H9B H 0.0936 0.2756 -0.0152 0.067 Uiso 1 1 calc R . . . .
C10 C 0.3253(5) 0.3134(2) 0.1084(3) 0.0623(9) Uani 1 1 d . . . . .
H10A H 0.3743 0.3042 0.1972 0.075 Uiso 1 1 calc R . . . .
H10B H 0.4109 0.2877 0.0622 0.075 Uiso 1 1 calc R . . . .
C11 C 0.3038(5) 0.4150(2) 0.0818(3) 0.0606(9) Uani 1 1 d . . . . .
H11 H 0.2482 0.4335 0.0012 0.073 Uiso 1 1 calc R . . . .
C12 C 0.3579(5) 0.4779(2) 0.1639(3) 0.0614(9) Uani 1 1 d . . . . .
H12 H 0.4075 0.4595 0.2457 0.074 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 1.212(3) . ?
O2 C8 1.210(3) . ?
O3 N2 1.211(3) . ?
O4 N2 1.214(3) . ?
N1 C1 1.390(4) . ?
N1 C8 1.392(4) . ?
N1 C9 1.454(4) . ?
N2 C12 1.446(4) . ?
C1 C2 1.485(4) . ?
C2 C3 1.374(4) . ?
C2 C7 1.383(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.374(4) . ?
C7 C8 1.486(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.510(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.494(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.279(4) . ?
C12 H12 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
C1 N1 C8 111.7(3) . . ?
C1 N1 C9 124.7(3) . . ?
C8 N1 C9 123.5(3) . . ?
O3 N2 O4 122.8(3) . . ?
O3 N2 C12 120.2(3) . . ?
O4 N2 C12 117.0(3) . . ?
O1 C1 N1 125.3(3) . . ?
O1 C1 C2 128.7(3) . . ?
N1 C1 C2 106.0(2) . . ?
C3 C2 C1 130.9(3) . . ?
C3 C2 C7 120.9(3) . . ?
C7 C2 C1 108.2(3) . . ?
C2 C3 H3 121.1 . . ?
C2 C3 C4 117.8(3) . . ?
C4 C3 H3 121.1 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 121.1 . . ?
C7 C6 C5 117.7(3) . . ?
C7 C6 H6 121.1 . . ?
C2 C7 C8 107.9(3) . . ?
C6 C7 C2 121.4(3) . . ?
C6 C7 C8 130.7(3) . . ?
O2 C8 N1 124.3(3) . . ?
O2 C8 C7 129.5(3) . . ?
N1 C8 C7 106.1(3) . . ?
N1 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
N1 C9 C10 112.1(3) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 C9 111.7(3) . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C10 C11 H11 118.2 . . ?
C12 C11 C10 123.5(3) . . ?
C12 C11 H11 118.2 . . ?
N2 C12 H12 118.3 . . ?
C11 C12 N2 123.3(3) . . ?
C11 C12 H12 118.3 . . ?

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
O1 C1 C2 C3 -0.5(6) . . . . ?
O1 C1 C2 C7 178.6(3) . . . . ?
O3 N2 C12 C11 7.8(6) . . . . ?
O4 N2 C12 C11 -173.8(4) . . . . ?
N1 C1 C2 C3 -179.5(3) . . . . ?
N1 C1 C2 C7 -0.5(3) . . . . ?
N1 C9 C10 C11 175.7(3) . . . . ?
C1 N1 C8 O2 179.1(3) . . . . ?
C1 N1 C8 C7 -0.6(3) . . . . ?
C1 N1 C9 C10 104.8(3) . . . . ?
C1 C2 C3 C4 -180.0(3) . . . . ?
C1 C2 C7 C6 179.9(3) . . . . ?
C1 C2 C7 C8 0.1(3) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C2 C7 C8 O2 -179.4(3) . . . . ?
C2 C7 C8 N1 0.3(3) . . . . ?
C3 C2 C7 C6 -0.9(5) . . . . ?
C3 C2 C7 C8 179.2(3) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C4 C5 C6 C7 -0.2(5) . . . . ?
C5 C6 C7 C2 0.5(5) . . . . ?
C5 C6 C7 C8 -179.8(3) . . . . ?
C6 C7 C8 O2 0.8(5) . . . . ?
C6 C7 C8 N1 -179.5(3) . . . . ?
C7 C2 C3 C4 1.1(5) . . . . ?
C8 N1 C1 O1 -178.4(3) . . . . ?
C8 N1 C1 C2 0.7(3) . . . . ?
C8 N1 C9 C10 -76.3(4) . . . . ?
C9 N1 C1 O1 0.6(5) . . . . ?
C9 N1 C1 C2 179.7(3) . . . . ?
C9 N1 C8 O2 0.1(5) . . . . ?
C9 N1 C8 C7 -179.6(3) . . . . ?
C9 C10 C11 C12 126.5(4) . . . . ?
C10 C11 C12 N2 176.5(3) . . . . ?


_olex2_date_sample_data_collection 2017-05-09
_olex2_submission_special_instructions 'No special instructions were received'
