# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_cxy3140_0m
_database_code_depnum_ccdc_archive 'CCDC 2115172'
loop_
_audit_author_name
_audit_author_address
'guo yonghong'
;Southern University of Science andTechnology 
China
;
_audit_update_record             
;
2021-10-12 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_audit_creation_date             2020-12-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 N3 O3'
_chemical_formula_sum            'C12 H9 N2 O3'
_chemical_formula_weight         229.21
_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                   7.8656(4)
_cell_length_b                   8.0258(4)
_cell_length_c                   9.6858(5)
_cell_angle_alpha                88.672(2)
_cell_angle_beta                 79.601(2)
_cell_angle_gamma                65.232(2)
_cell_volume                     545.14(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5253
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      4.65
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6312
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0783 before and 0.0450 after correction.
The Ratio of minimum to maximum transmission is 0.8381.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             238
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6663
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.394
_diffrn_reflns_theta_min         6.083
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1872
_reflns_number_total             2001
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2001
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.045
_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)+(0.0338P)²+0.1780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0826
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.37719(12) 0.02238(11) 0.24371(9) 0.0288(2) Uani 1 1 d . . . . .
O2 O 0.54812(12) 0.23237(12) 0.41784(9) 0.0327(2) Uani 1 1 d . . . . .
O3 O 0.65871(12) -0.05942(11) 0.09639(9) 0.0288(2) Uani 1 1 d . . . . .
N1 N 0.62927(15) 0.29790(14) 0.10698(11) 0.0312(3) Uani 1 1 d . . . . .
N2 N 0.94097(18) 0.1344(2) 0.15339(15) 0.0499(3) Uani 1 1 d . . . . .
C1 C 0.3993(2) -0.16654(17) 0.24195(14) 0.0344(3) Uani 1 1 d . . . . .
H1A H 0.388840 -0.202567 0.148969 0.052 Uiso 1 1 calc GR . . . .
H1B H 0.299401 -0.177226 0.313316 0.052 Uiso 1 1 calc GR . . . .
H1C H 0.524654 -0.247332 0.262396 0.052 Uiso 1 1 calc GR . . . .
C2 C 0.51662(16) 0.05400(15) 0.16639(11) 0.0221(2) Uani 1 1 d . . . . .
C3 C 0.47149(16) 0.25720(15) 0.18293(12) 0.0240(3) Uani 1 1 d . . . . .
C4 C 0.43783(16) 0.31477(15) 0.34157(12) 0.0236(3) Uani 1 1 d . . . . .
C5 C 0.26046(16) 0.48271(15) 0.37237(12) 0.0237(3) Uani 1 1 d . . . . .
C6 C 0.18049(17) 0.59132(16) 0.49755(13) 0.0283(3) Uani 1 1 d . . . . .
H6 H 0.240234 0.560026 0.577223 0.034 Uiso 1 1 calc R . . . .
C7 C 0.01160(19) 0.74596(17) 0.50214(15) 0.0342(3) Uani 1 1 d . . . . .
H7 H -0.046192 0.823084 0.585910 0.041 Uiso 1 1 calc R . . . .
C8 C 0.17572(17) 0.52503(15) 0.25478(13) 0.0247(3) Uani 1 1 d . . . . .
C9 C 0.00539(18) 0.68055(17) 0.26017(14) 0.0316(3) Uani 1 1 d . . . . .
H9 H -0.054740 0.711431 0.180669 0.038 Uiso 1 1 calc R . . . .
C10 C -0.07457(18) 0.78943(17) 0.38427(15) 0.0365(3) Uani 1 1 d . . . . .
H10 H -0.190821 0.896235 0.389239 0.044 Uiso 1 1 calc R . . . .
C11 C 0.28785(17) 0.38599(16) 0.13291(13) 0.0273(3) Uani 1 1 d . . . . .
H11A H 0.317516 0.446912 0.047833 0.033 Uiso 1 1 calc R . . . .
H11B H 0.215818 0.317123 0.111428 0.033 Uiso 1 1 calc R . . . .
N3 N 0.78790(16) 0.20608(15) 0.13847(11) 0.0331(3) 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 1.4521(14) . ?
O1 C2 1.3250(14) . ?
O2 C4 1.2098(14) . ?
O3 C2 1.2000(14) . ?
N1 C3 1.4789(15) . ?
N1 N3 1.2447(16) . ?
N2 N3 1.1315(17) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.5224(15) . ?
C3 C4 1.5582(16) . ?
C3 C11 1.5388(16) . ?
C4 C5 1.4645(16) . ?
C5 C6 1.3927(17) . ?
C5 C8 1.3869(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.3809(18) . ?
C7 H7 0.9500 . ?
C7 C10 1.395(2) . ?
C8 C9 1.3900(17) . ?
C8 C11 1.5089(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(2) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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
C2 O1 C1 116.55(9) . . ?
N3 N1 C3 115.36(10) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 109.35(9) . . ?
O3 C2 O1 125.77(10) . . ?
O3 C2 C3 124.86(10) . . ?
N1 C3 C2 111.63(9) . . ?
N1 C3 C4 108.23(9) . . ?
N1 C3 C11 107.83(9) . . ?
C2 C3 C4 109.65(9) . . ?
C2 C3 C11 114.06(9) . . ?
C11 C3 C4 105.10(9) . . ?
O2 C4 C3 123.15(10) . . ?
O2 C4 C5 129.45(11) . . ?
C5 C4 C3 107.36(9) . . ?
C6 C5 C4 127.94(11) . . ?
C8 C5 C4 109.88(10) . . ?
C8 C5 C6 122.17(11) . . ?
C5 C6 H6 121.1 . . ?
C7 C6 C5 117.88(12) . . ?
C7 C6 H6 121.1 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C10 120.29(12) . . ?
C10 C7 H7 119.9 . . ?
C5 C8 C9 119.69(11) . . ?
C5 C8 C11 112.34(10) . . ?
C9 C8 C11 127.96(11) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 C8 118.40(12) . . ?
C10 C9 H9 120.8 . . ?
C7 C10 H10 119.2 . . ?
C9 C10 C7 121.57(12) . . ?
C9 C10 H10 119.2 . . ?
C3 C11 H11A 110.8 . . ?
C3 C11 H11B 110.8 . . ?
C8 C11 C3 104.55(9) . . ?
C8 C11 H11A 110.8 . . ?
C8 C11 H11B 110.8 . . ?
H11A C11 H11B 108.9 . . ?
N2 N3 N1 170.80(13) . . ?

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 C2 C3 N1 175.83(9) . . . . ?
O1 C2 C3 C4 55.89(12) . . . . ?
O1 C2 C3 C11 -61.64(12) . . . . ?
O2 C4 C5 C6 2.5(2) . . . . ?
O2 C4 C5 C8 -177.82(12) . . . . ?
O3 C2 C3 N1 -2.68(16) . . . . ?
O3 C2 C3 C4 -122.62(12) . . . . ?
O3 C2 C3 C11 119.85(12) . . . . ?
N1 C3 C4 O2 -70.92(14) . . . . ?
N1 C3 C4 C5 106.79(10) . . . . ?
N1 C3 C11 C8 -106.84(10) . . . . ?
C1 O1 C2 O3 -0.45(17) . . . . ?
C1 O1 C2 C3 -178.94(9) . . . . ?
C2 C3 C4 O2 51.08(14) . . . . ?
C2 C3 C4 C5 -131.22(9) . . . . ?
C2 C3 C11 C8 128.57(10) . . . . ?
C3 C4 C5 C6 -174.98(11) . . . . ?
C3 C4 C5 C8 4.67(12) . . . . ?
C4 C3 C11 C8 8.44(11) . . . . ?
C4 C5 C6 C7 179.36(11) . . . . ?
C4 C5 C8 C9 -179.63(10) . . . . ?
C4 C5 C8 C11 0.97(13) . . . . ?
C5 C6 C7 C10 0.26(18) . . . . ?
C5 C8 C9 C10 0.14(18) . . . . ?
C5 C8 C11 C3 -6.18(13) . . . . ?
C6 C5 C8 C9 0.04(17) . . . . ?
C6 C5 C8 C11 -179.36(10) . . . . ?
C6 C7 C10 C9 -0.1(2) . . . . ?
C8 C5 C6 C7 -0.24(17) . . . . ?
C8 C9 C10 C7 -0.13(19) . . . . ?
C9 C8 C11 C3 174.48(11) . . . . ?
C11 C3 C4 O2 174.08(11) . . . . ?
C11 C3 C4 C5 -8.22(12) . . . . ?
C11 C8 C9 C10 179.44(11) . . . . ?
N3 N1 C3 C2 -55.23(14) . . . . ?
N3 N1 C3 C4 65.53(13) . . . . ?
N3 N1 C3 C11 178.73(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
