# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_M266
_database_code_depnum_ccdc_archive 'CCDC 2280426'
loop_
_audit_author_name
_audit_author_address
'Shi Yang'
;sichuan university
China
;
_audit_update_record             
;
2023-07-10 deposited with the CCDC.	2023-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6 N2 O2'
_chemical_formula_weight         174.16

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   3.7781(2)
_cell_length_b                   7.5804(3)
_cell_length_c                   14.7776(6)
_cell_angle_alpha                94.101(2)
_cell_angle_beta                 93.691(2)
_cell_angle_gamma                96.948(2)
_cell_volume                     417.90(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5946
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      29.51

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             180
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.099
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7132
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   
; 
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0870 before and 0.0486 after correction. 
The Ratio of minimum to maximum transmission is 0.9562. 
The λ/2 correction factor is Not present. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus Sealed Tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11723
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.723
_diffrn_reflns_theta_max         29.553
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2329
_reflns_number_gt                2110
_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_bruker_data_scaling   'SADABS V2016/2 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX4 v2021.10-1 (Bruker AXS)'
_computing_data_collection       'APEX4 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'

_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)+(0.0672P)²+0.0785P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual Space'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2329
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
O1 O 0.28030(19) 0.11039(9) 0.58259(5) 0.02292(17) Uani 1 1 d . . . . .
O2 O 0.22541(17) 0.47454(8) 0.40494(4) 0.02106(17) Uani 1 1 d . . . . .
N1 N 0.3737(2) 0.20622(10) 0.44271(5) 0.01774(17) Uani 1 1 d . . . . .
N2 N 0.9227(3) 0.22264(13) -0.04524(6) 0.0306(2) Uani 1 1 d . . . . .
H1 H 0.474(4) 0.108(2) 0.4279(10) 0.033(3) Uiso 1 1 d . . . . .
C1 C 0.2489(2) 0.22143(11) 0.52785(6) 0.01771(18) Uani 1 1 d . . . . .
H1A H 0.133854 0.322274 0.544698 0.021 Uiso 1 1 calc R U . . .
C2 C 0.3462(2) 0.33739(11) 0.38275(6) 0.01644(18) Uani 1 1 d . . . . .
C3 C 0.4721(2) 0.30288(11) 0.29014(6) 0.01692(18) Uani 1 1 d . . . . .
C4 C 0.5226(2) 0.13384(12) 0.25357(6) 0.01958(19) Uani 1 1 d . . . . .
H4 H 0.478497 0.033704 0.288248 0.023 Uiso 1 1 calc R U . . .
C5 C 0.6372(2) 0.11161(12) 0.16645(6) 0.0212(2) Uani 1 1 d . . . . .
H5 H 0.671529 -0.003352 0.141204 0.025 Uiso 1 1 calc R U . . .
C6 C 0.7013(2) 0.26000(13) 0.11657(6) 0.0207(2) Uani 1 1 d . . . . .
C7 C 0.6509(3) 0.42985(13) 0.15251(6) 0.0235(2) Uani 1 1 d . . . . .
H7 H 0.695283 0.530046 0.117889 0.028 Uiso 1 1 calc R U . . .
C8 C 0.5354(2) 0.45032(12) 0.23929(6) 0.0214(2) Uani 1 1 d . . . . .
H8 H 0.499078 0.565149 0.264301 0.026 Uiso 1 1 calc R U . . .
C9 C 0.8238(3) 0.23828(13) 0.02636(7) 0.0244(2) 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 C1 1.2192(11) . ?
O2 C2 1.2173(10) . ?
N1 C1 1.3737(11) . ?
N1 C2 1.3870(11) . ?
N1 H1 0.892(15) . ?
N2 C9 1.1477(13) . ?
C1 H1A 0.9500 . ?
C2 C3 1.4934(12) . ?
C3 C4 1.3941(12) . ?
C3 C8 1.3963(12) . ?
C4 C5 1.3900(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.3939(13) . ?
C5 H5 0.9500 . ?
C6 C7 1.3966(13) . ?
C6 C9 1.4438(12) . ?
C7 C8 1.3853(12) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?

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 C2 121.44(7) . . ?
C1 N1 H1 116.9(9) . . ?
C2 N1 H1 121.7(9) . . ?
O1 C1 N1 122.48(8) . . ?
O1 C1 H1A 118.8 . . ?
N1 C1 H1A 118.8 . . ?
O2 C2 N1 121.30(8) . . ?
O2 C2 C3 121.67(8) . . ?
N1 C2 C3 117.03(7) . . ?
C4 C3 C8 120.14(8) . . ?
C4 C3 C2 123.30(8) . . ?
C8 C3 C2 116.56(8) . . ?
C5 C4 C3 120.09(8) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.21(8) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C7 121.14(8) . . ?
C5 C6 C9 119.55(8) . . ?
C7 C6 C9 119.31(8) . . ?
C8 C7 C6 119.14(8) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C3 120.27(8) . . ?
C7 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
N2 C9 C6 179.35(11) . . ?

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 N1 C1 O1 -177.69(8) . . . . ?
C1 N1 C2 O2 3.43(13) . . . . ?
C1 N1 C2 C3 -176.74(7) . . . . ?
O2 C2 C3 C4 -162.53(9) . . . . ?
N1 C2 C3 C4 17.64(12) . . . . ?
O2 C2 C3 C8 16.66(12) . . . . ?
N1 C2 C3 C8 -163.17(8) . . . . ?
C8 C3 C4 C5 0.22(13) . . . . ?
C2 C3 C4 C5 179.38(8) . . . . ?
C3 C4 C5 C6 0.12(13) . . . . ?
C4 C5 C6 C7 -0.25(14) . . . . ?
C4 C5 C6 C9 179.41(8) . . . . ?
C5 C6 C7 C8 0.04(14) . . . . ?
C9 C6 C7 C8 -179.62(8) . . . . ?
C6 C7 C8 C3 0.31(14) . . . . ?
C4 C3 C8 C7 -0.44(14) . . . . ?
C2 C3 C8 C7 -179.66(8) . . . . ?

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
N1 H1 O1 0.892(15) 1.998(15) 2.8814(10) 170.3(13) 2_656 yes
C1 H1A O2 0.95 2.29 3.2266(10) 168.9 2_566 yes

_refine_diff_density_max         0.449
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.049

