# Supplementary Information (SI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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_MIBA
_audit_block_doi                 10.5517/ccdc.csd.cc2lg3fm
_database_code_depnum_ccdc_archive 'CCDC 2396840'
loop_
_audit_author_name
_audit_author_address
MIBA
;College of Chemistry and Green Catalysis Center 
China
;
_audit_update_record             
;
2024-11-04 deposited with the CCDC.	2025-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 N2 O2'
_chemical_formula_weight         202.21

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   3.9005(4)
_cell_length_b                   7.2565(6)
_cell_length_c                   17.1927(14)
_cell_angle_alpha                90
_cell_angle_beta                 94.660(3)
_cell_angle_gamma                90
_cell_volume                     485.01(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4282
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      27.33

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             212
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10045
_diffrn_reflns_av_unetI/netI     0.0884
_diffrn_reflns_av_R_equivalents  0.0980
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.049
_diffrn_reflns_theta_max         27.442
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2168
_reflns_number_gt                1489
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_max     0.969
_reflns_Friedel_fraction_full    0.993

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0495P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 528 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2168
_refine_ls_number_parameters     137
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.004
_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
N2 N 0.7066(5) 0.7124(2) 0.14246(10) 0.0371(5) Uani 1 1 d . . . . .
O1 O 0.1755(7) 0.0444(3) 0.34511(13) 0.0770(7) Uani 1 1 d . . . . .
O2 O 0.1971(5) 0.2759(3) 0.42968(11) 0.0634(6) Uani 1 1 d . . . . .
N1 N 0.7917(7) 0.8392(3) 0.02816(12) 0.0559(6) Uani 1 1 d . . . . .
C4 C 0.5895(6) 0.5865(3) 0.19736(13) 0.0344(6) Uani 1 1 d . . . . .
C9 C 0.4073(7) 0.5238(4) 0.32350(14) 0.0455(7) Uani 1 1 d . . . . .
H9 H 0.3605 0.5651 0.3727 0.055 Uiso 1 1 calc R U . . .
C1 C 0.6705(7) 0.6969(4) 0.06280(14) 0.0484(6) Uani 1 1 d . . . . .
H1 H 0.5705 0.5960 0.0365 0.058 Uiso 1 1 calc R U . . .
C10 C 0.5215(7) 0.6456(3) 0.27108(14) 0.0454(7) Uani 1 1 d . . . . .
H10 H 0.5539 0.7686 0.2849 0.055 Uiso 1 1 calc R U . . .
C6 C 0.4252(7) 0.2819(4) 0.23098(14) 0.0476(7) Uani 1 1 d . . . . .
H6 H 0.3918 0.1588 0.2174 0.057 Uiso 1 1 calc R U . . .
C7 C 0.3594(6) 0.3390(4) 0.30459(15) 0.0413(6) Uani 1 1 d . . . . .
C8 C 0.2356(7) 0.2034(4) 0.35966(15) 0.0498(7) Uani 1 1 d . . . . .
C3 C 0.8627(6) 0.8800(3) 0.15756(15) 0.0457(6) Uani 1 1 d . . . . .
H3 H 0.9217 0.9320 0.2063 0.055 Uiso 1 1 calc R U . . .
C2 C 0.9129(7) 0.9538(4) 0.08732(14) 0.0493(6) Uani 1 1 d . . . . .
H2 H 1.0162 1.0674 0.0801 0.059 Uiso 1 1 calc R U . . .
C5 C 0.5389(7) 0.4023(3) 0.17691(15) 0.0469(7) Uani 1 1 d . . . . .
H5 H 0.5814 0.3612 0.1274 0.056 Uiso 1 1 calc R U . . .
C11 C 0.0780(10) 0.1518(5) 0.4874(2) 0.0809(11) Uani 1 1 d . . . . .
H11A H -0.1456 0.1058 0.4697 0.121 Uiso 1 1 calc R U . . .
H11B H 0.0646 0.2165 0.5358 0.121 Uiso 1 1 calc R U . . .
H11C H 0.2357 0.0507 0.4951 0.121 Uiso 1 1 calc R U . . .


_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
N2 C1 1.370(3) . ?
N2 C3 1.376(3) . ?
N2 C4 1.415(3) . ?
O1 C8 1.200(4) . ?
O2 C8 1.334(3) . ?
O2 C11 1.445(3) . ?
N1 C1 1.300(3) . ?
N1 C2 1.368(3) . ?
C4 C10 1.384(3) . ?
C4 C5 1.393(3) . ?
C9 C10 1.363(4) . ?
C9 C7 1.389(4) . ?
C9 H9 0.9300 . ?
C1 H1 0.9300 . ?
C10 H10 0.9300 . ?
C6 C5 1.375(4) . ?
C6 C7 1.375(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.474(4) . ?
C3 C2 1.350(3) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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 N2 C3 105.6(2) . . ?
C1 N2 C4 127.0(2) . . ?
C3 N2 C4 127.3(2) . . ?
C8 O2 C11 116.1(3) . . ?
C1 N1 C2 105.0(2) . . ?
C10 C4 C5 119.6(2) . . ?
C10 C4 N2 120.5(2) . . ?
C5 C4 N2 119.9(2) . . ?
C10 C9 C7 121.1(2) . . ?
C10 C9 H9 119.5 . . ?
C7 C9 H9 119.5 . . ?
N1 C1 N2 112.4(2) . . ?
N1 C1 H1 123.8 . . ?
N2 C1 H1 123.8 . . ?
C9 C10 C4 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C4 C10 H10 119.9 . . ?
C5 C6 C7 121.7(2) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C9 118.3(2) . . ?
C6 C7 C8 119.0(2) . . ?
C9 C7 C8 122.6(2) . . ?
O1 C8 O2 122.3(3) . . ?
O1 C8 C7 125.2(3) . . ?
O2 C8 C7 112.5(3) . . ?
C2 C3 N2 106.0(2) . . ?
C2 C3 H3 127.0 . . ?
N2 C3 H3 127.0 . . ?
C3 C2 N1 111.0(2) . . ?
C3 C2 H2 124.5 . . ?
N1 C2 H2 124.5 . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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 N2 C4 C10 -155.0(2) . . . . ?
C3 N2 C4 C10 21.0(3) . . . . ?
C1 N2 C4 C5 24.3(3) . . . . ?
C3 N2 C4 C5 -159.6(2) . . . . ?
C2 N1 C1 N2 0.0(3) . . . . ?
C3 N2 C1 N1 0.3(3) . . . . ?
C4 N2 C1 N1 177.1(2) . . . . ?
C7 C9 C10 C4 0.5(4) . . . . ?
C5 C4 C10 C9 0.3(4) . . . . ?
N2 C4 C10 C9 179.7(2) . . . . ?
C5 C6 C7 C9 0.7(4) . . . . ?
C5 C6 C7 C8 179.6(2) . . . . ?
C10 C9 C7 C6 -1.0(4) . . . . ?
C10 C9 C7 C8 -179.9(2) . . . . ?
C11 O2 C8 O1 0.0(4) . . . . ?
C11 O2 C8 C7 -179.7(2) . . . . ?
C6 C7 C8 O1 -2.4(4) . . . . ?
C9 C7 C8 O1 176.5(3) . . . . ?
C6 C7 C8 O2 177.3(2) . . . . ?
C9 C7 C8 O2 -3.9(4) . . . . ?
C1 N2 C3 C2 -0.4(3) . . . . ?
C4 N2 C3 C2 -177.2(2) . . . . ?
N2 C3 C2 N1 0.4(3) . . . . ?
C1 N1 C2 C3 -0.2(3) . . . . ?
C7 C6 C5 C4 0.2(4) . . . . ?
C10 C4 C5 C6 -0.7(4) . . . . ?
N2 C4 C5 C6 180.0(2) . . . . ?

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
C3 H3 O1 0.93 2.64 3.559(3) 170.8 1_665
C1 H1 N1 0.93 2.54 3.460(4) 170.9 2_645

_refine_diff_density_max         0.111
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_a
_audit_block_doi                 10.5517/ccdc.csd.cc2m9n4r
_database_code_depnum_ccdc_archive 'CCDC 2422344'
loop_
_citation_id
_citation_doi
_citation_year
1 https://doi.org/10.1039/D4QM01037J 2025
loop_
_audit_author_name
_audit_author_address
HIBA
;College of Chemistry and Green Catalysis Center, Zhengzhou University
China
;
_audit_update_record             
;
2025-02-08 deposited with the CCDC.	2025-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 N2 O2'
_chemical_formula_weight         188.18

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      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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'

_cell_length_a                   4.1240(9)
_cell_length_b                   6.6158(14)
_cell_length_c                   15.347(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.222(7)
_cell_angle_gamma                90
_cell_volume                     417.58(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2470
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      26.18

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             196
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5298
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.662
_diffrn_reflns_theta_max         27.069
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_point_group_measured_fraction_full 0.926
_reflns_number_total             1619
_reflns_number_gt                1239
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_max     0.769
_reflns_Friedel_fraction_full    0.853

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0743P)²+0.1748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 451 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1619
_refine_ls_number_parameters     128
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1655
_refine_ls_wR_factor_gt          0.1445
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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
O2 O 1.0773(11) 0.7481(6) 0.6386(3) 0.0562(12) Uani 1 1 d . . . . .
H2 H 1.1791 0.7984 0.6811 0.084 Uiso 1 1 calc R U . . .
O1 O 1.0891(11) 0.4791(6) 0.7253(2) 0.0588(12) Uani 1 1 d . . . . .
N2 N 0.2450(10) 0.1456(6) 0.3916(3) 0.0397(10) Uani 1 1 d . . . . .
N1 N -0.0856(11) 0.0979(8) 0.2737(3) 0.0478(11) Uani 1 1 d . . . . .
C10 C 1.0071(13) 0.5582(8) 0.6559(3) 0.0443(14) Uani 1 1 d . . . . .
C7 C 0.8141(13) 0.4527(8) 0.5864(4) 0.0401(12) Uani 1 1 d . . . . .
C4 C 0.4413(12) 0.2468(7) 0.4569(3) 0.0382(12) Uani 1 1 d . . . . .
C9 C 0.5449(13) 0.4408(8) 0.4425(3) 0.0441(13) Uani 1 1 d . . . . .
H9 H 0.4923 0.5026 0.3889 0.053 Uiso 1 1 calc R U . . .
C8 C 0.7248(13) 0.5430(8) 0.5066(3) 0.0459(14) Uani 1 1 d . . . . .
H8 H 0.7884 0.6753 0.4965 0.055 Uiso 1 1 calc R U . . .
C3 C 0.0816(14) 0.2305(8) 0.3215(3) 0.0451(14) Uani 1 1 d . . . . .
H3 H 0.0872 0.3678 0.3087 0.054 Uiso 1 1 calc R U . . .
C5 C 0.5278(14) 0.1539(8) 0.5362(3) 0.0474(14) Uani 1 1 d . . . . .
H5 H 0.4600 0.0227 0.5467 0.057 Uiso 1 1 calc R U . . .
C1 C 0.1717(15) -0.0569(8) 0.3869(5) 0.0547(16) Uani 1 1 d . . . . .
H1 H 0.2478 -0.1564 0.4261 0.066 Uiso 1 1 calc R U . . .
C6 C 0.7138(14) 0.2572(8) 0.5989(3) 0.0501(15) Uani 1 1 d . . . . .
H6 H 0.7744 0.1932 0.6515 0.060 Uiso 1 1 calc R U . . .
C2 C -0.0299(15) -0.0840(9) 0.3155(4) 0.0546(15) Uani 1 1 d . . . . .
H2A H -0.1188 -0.2072 0.2969 0.066 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C10 1.320(7) . ?
O2 H2 0.8200 . ?
O1 C10 1.213(6) . ?
N2 C3 1.349(6) . ?
N2 C1 1.374(7) . ?
N2 C4 1.411(7) . ?
N1 C3 1.307(7) . ?
N1 C2 1.375(7) . ?
C10 C7 1.460(8) . ?
C7 C6 1.376(8) . ?
C7 C8 1.388(7) . ?
C4 C9 1.376(6) . ?
C4 C5 1.386(7) . ?
C9 C8 1.366(7) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C3 H3 0.9300 . ?
C5 C6 1.368(8) . ?
C5 H5 0.9300 . ?
C1 C2 1.339(8) . ?
C1 H1 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2A 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
C10 O2 H2 109.5 . . ?
C3 N2 C1 105.6(5) . . ?
C3 N2 C4 126.6(4) . . ?
C1 N2 C4 127.8(4) . . ?
C3 N1 C2 105.2(5) . . ?
O1 C10 O2 122.4(5) . . ?
O1 C10 C7 122.5(5) . . ?
O2 C10 C7 115.1(5) . . ?
C6 C7 C8 117.7(5) . . ?
C6 C7 C10 120.1(5) . . ?
C8 C7 C10 122.2(5) . . ?
C9 C4 C5 119.5(5) . . ?
C9 C4 N2 119.8(5) . . ?
C5 C4 N2 120.7(4) . . ?
C8 C9 C4 120.3(5) . . ?
C8 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?
C9 C8 C7 121.1(5) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
N1 C3 N2 112.3(5) . . ?
N1 C3 H3 123.8 . . ?
N2 C3 H3 123.8 . . ?
C6 C5 C4 119.4(5) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C2 C1 N2 107.1(5) . . ?
C2 C1 H1 126.4 . . ?
N2 C1 H1 126.4 . . ?
C5 C6 C7 122.0(5) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C1 C2 N1 109.7(5) . . ?
C1 C2 H2A 125.2 . . ?
N1 C2 H2A 125.2 . . ?

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 C10 C7 C6 1.0(8) . . . . ?
O2 C10 C7 C6 -177.0(6) . . . . ?
O1 C10 C7 C8 -179.1(6) . . . . ?
O2 C10 C7 C8 2.9(8) . . . . ?
C3 N2 C4 C9 -15.8(8) . . . . ?
C1 N2 C4 C9 166.3(6) . . . . ?
C3 N2 C4 C5 163.3(5) . . . . ?
C1 N2 C4 C5 -14.6(8) . . . . ?
C5 C4 C9 C8 -1.6(8) . . . . ?
N2 C4 C9 C8 177.5(5) . . . . ?
C4 C9 C8 C7 1.7(8) . . . . ?
C6 C7 C8 C9 -0.3(8) . . . . ?
C10 C7 C8 C9 179.8(5) . . . . ?
C2 N1 C3 N2 0.5(7) . . . . ?
C1 N2 C3 N1 -0.3(7) . . . . ?
C4 N2 C3 N1 -178.5(5) . . . . ?
C9 C4 C5 C6 0.2(8) . . . . ?
N2 C4 C5 C6 -178.9(5) . . . . ?
C3 N2 C1 C2 -0.1(7) . . . . ?
C4 N2 C1 C2 178.1(5) . . . . ?
C4 C5 C6 C7 1.2(9) . . . . ?
C8 C7 C6 C5 -1.1(9) . . . . ?
C10 C7 C6 C5 178.8(5) . . . . ?
N2 C1 C2 N1 0.4(7) . . . . ?
C3 N1 C2 C1 -0.6(7) . . . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.066

