# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1974489'
loop_
_audit_author_name
_audit_author_address
'Kai-kai Wang'
;xinxiang University
China
;
_audit_update_record             
;
2019-12-28 deposited with the CCDC.	2021-12-03 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            'C14 H11 N O3'
_chemical_formula_weight         241.24

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.9979(11)
_cell_length_b                   9.4469(11)
_cell_length_c                   14.0932(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1198.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2636
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.13

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.977
_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      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6084
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.891
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2107
_reflns_number_gt                1859
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0715P)²+0.0275P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 700 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   1.3(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2107
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0983
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_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
C1 C 0.4616(2) 0.7407(2) 0.67369(15) 0.0448(5) Uani 1 1 d . . . . .
H1D H 0.5214 0.8100 0.6465 0.054 Uiso 1 1 calc R U . . .
C2 C 0.4632(3) 0.7200(3) 0.77135(16) 0.0541(6) Uani 1 1 d . . . . .
H2B H 0.5236 0.7760 0.8095 0.065 Uiso 1 1 calc R U . . .
C3 C 0.3753(3) 0.6167(3) 0.81170(16) 0.0519(6) Uani 1 1 d . . . . .
H3A H 0.3767 0.6031 0.8770 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2860(3) 0.5341(3) 0.75599(15) 0.0512(6) Uani 1 1 d . . . . .
H4A H 0.2272 0.4644 0.7836 0.061 Uiso 1 1 calc R U . . .
C5 C 0.2828(2) 0.5538(2) 0.65855(15) 0.0448(5) Uani 1 1 d . . . . .
H5D H 0.2219 0.4974 0.6210 0.054 Uiso 1 1 calc R U . . .
C6 C 0.3707(2) 0.6577(2) 0.61689(13) 0.0348(5) Uani 1 1 d . . . . .
C7 C 0.3587(2) 0.6759(2) 0.51183(13) 0.0367(5) Uani 1 1 d . . . . .
C8 C 0.3962(2) 0.8573(2) 0.33583(14) 0.0442(5) Uani 1 1 d . . . . .
C9 C 0.3934(2) 0.8549(2) 0.23051(14) 0.0396(5) Uani 1 1 d . . . . .
C10 C 0.4795(3) 0.7633(3) 0.17723(15) 0.0497(6) Uani 1 1 d . . . . .
H10B H 0.5412 0.6982 0.2072 0.060 Uiso 1 1 calc R U . . .
C11 C 0.4733(3) 0.7690(3) 0.07917(16) 0.0610(7) Uani 1 1 d . . . . .
H11 H 0.5318 0.7085 0.0429 0.073 Uiso 1 1 calc R U . . .
C12 C 0.3796(3) 0.8649(3) 0.03525(16) 0.0629(7) Uani 1 1 d . . . . .
H12 H 0.3752 0.8684 -0.0306 0.075 Uiso 1 1 calc R U . . .
C13 C 0.2932(3) 0.9547(3) 0.08806(16) 0.0626(7) Uani 1 1 d . . . . .
H13A H 0.2295 1.0180 0.0580 0.075 Uiso 1 1 calc R U . . .
C14 C 0.3007(3) 0.9511(2) 0.18597(16) 0.0514(6) Uani 1 1 d . . . . .
H14A H 0.2435 1.0132 0.2219 0.062 Uiso 1 1 calc R U . . .
N1 N 0.4756(2) 0.7354(2) 0.46961(11) 0.0507(5) Uani 1 1 d . . . . .
H1E H 0.5491 0.7677 0.5021 0.061 Uiso 1 1 calc R U . . .
O1 O 0.24811(16) 0.63895(17) 0.46702(9) 0.0490(4) Uani 1 1 d . . . . .
O2 O 0.47436(17) 0.74343(17) 0.37033(9) 0.0488(4) Uani 1 1 d . . . . .
O3 O 0.3400(3) 0.9430(2) 0.38571(11) 0.0760(6) 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
C1 C6 1.387(3) . ?
C1 C2 1.390(3) . ?
C1 H1D 0.9300 . ?
C2 C3 1.379(3) . ?
C2 H2B 0.9300 . ?
C3 C4 1.368(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.391(3) . ?
C5 H5D 0.9300 . ?
C6 C7 1.495(3) . ?
C7 O1 1.229(2) . ?
C7 N1 1.333(3) . ?
C8 O3 1.186(3) . ?
C8 O2 1.374(3) . ?
C8 C9 1.485(3) . ?
C9 C14 1.384(3) . ?
C9 C10 1.383(3) . ?
C10 C11 1.384(3) . ?
C10 H10B 0.9300 . ?
C11 C12 1.384(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(3) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
N1 O2 1.401(2) . ?
N1 H1E 0.8600 . ?

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
C6 C1 C2 119.9(2) . . ?
C6 C1 H1D 120.1 . . ?
C2 C1 H1D 120.1 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2B 120.0 . . ?
C1 C2 H2B 120.0 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5D 120.0 . . ?
C6 C5 H5D 120.0 . . ?
C1 C6 C5 119.38(18) . . ?
C1 C6 C7 123.31(18) . . ?
C5 C6 C7 117.29(17) . . ?
O1 C7 N1 121.97(17) . . ?
O1 C7 C6 122.32(18) . . ?
N1 C7 C6 115.71(16) . . ?
O3 C8 O2 122.91(18) . . ?
O3 C8 C9 126.6(2) . . ?
O2 C8 C9 110.53(18) . . ?
C14 C9 C10 120.14(19) . . ?
C14 C9 C8 116.98(19) . . ?
C10 C9 C8 122.88(19) . . ?
C9 C10 C11 119.7(2) . . ?
C9 C10 H10B 120.1 . . ?
C11 C10 H10B 120.1 . . ?
C10 C11 C12 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.9(2) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C9 C14 C13 119.9(2) . . ?
C9 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C7 N1 O2 117.52(16) . . ?
C7 N1 H1E 121.2 . . ?
O2 N1 H1E 121.2 . . ?
C8 O2 N1 113.56(16) . . ?

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
C6 C1 C2 C3 0.4(4) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C1 C6 C7 178.0(2) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 -178.3(2) . . . . ?
C1 C6 C7 O1 -155.1(2) . . . . ?
C5 C6 C7 O1 23.4(3) . . . . ?
C1 C6 C7 N1 24.6(3) . . . . ?
C5 C6 C7 N1 -156.80(19) . . . . ?
O3 C8 C9 C14 -9.0(3) . . . . ?
O2 C8 C9 C14 170.81(19) . . . . ?
O3 C8 C9 C10 170.3(3) . . . . ?
O2 C8 C9 C10 -9.9(3) . . . . ?
C14 C9 C10 C11 0.5(3) . . . . ?
C8 C9 C10 C11 -178.8(2) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C10 C9 C14 C13 0.6(3) . . . . ?
C8 C9 C14 C13 179.9(2) . . . . ?
C12 C13 C14 C9 -1.2(4) . . . . ?
O1 C7 N1 O2 -5.5(3) . . . . ?
C6 C7 N1 O2 174.67(16) . . . . ?
O3 C8 O2 N1 2.6(3) . . . . ?
C9 C8 O2 N1 -177.23(16) . . . . ?
C7 N1 O2 C8 82.9(2) . . . . ?

_refine_diff_density_max         0.127
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.026

