# 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_pc
_database_code_depnum_ccdc_archive 'CCDC 2034932'
loop_
_audit_author_name
_audit_author_address
'Lieqiang Liao'
;Gannan Normal University
China
;
_audit_update_record             
;
2020-10-01 deposited with the CCDC.	2021-03-02 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         'C17 H13 N5 O2, H2 O'
_chemical_formula_sum            'C17 H15 N5 O3'
_chemical_formula_weight         337.34

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.6401(3)
_cell_length_b                   8.4503(2)
_cell_length_c                   13.3398(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.159(3)
_cell_angle_gamma                90
_cell_volume                     1528.42(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6332
_cell_measurement_theta_min      3.2700
_cell_measurement_theta_max      79.2380

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.868
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10226
_diffrn_reflns_av_unetI/netI     0.0810
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.259
_diffrn_reflns_theta_max         79.523
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3260
_reflns_number_gt                3024
_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_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+40.7281P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3260
_refine_ls_number_parameters     169
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1897
_refine_ls_R_factor_gt           0.1837
_refine_ls_wR_factor_ref         0.4077
_refine_ls_wR_factor_gt          0.4051
_refine_ls_goodness_of_fit_ref   1.207
_refine_ls_restrained_S_all      1.211
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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 0.5151(3) 0.4038(6) 0.3893(4) 0.0167(10) Uani 1 1 d . . . . .
N2 N 0.3496(4) -0.1481(6) 0.2889(4) 0.0148(12) Uani 1 1 d . . . . .
N3 N 0.9767(4) 0.2755(8) 0.5118(4) 0.0232(14) Uani 1 1 d . U . . .
H3 H 0.9243 0.2607 0.4524 0.028 Uiso 1 1 calc R U . . .
N4 N 0.7631(4) 0.6036(7) 0.6243(4) 0.0186(13) Uani 1 1 d . . . . .
N5 N 1.2300(4) 0.0329(6) 0.5169(4) 0.0127(6) Uani 1 1 d . . . . .
N6 N 0.5911(3) 0.1613(6) 0.4174(4) 0.0128(11) Uani 1 1 d . . . . .
H6 H 0.6492 0.1148 0.4423 0.015 Uiso 1 1 calc R U . . .
O7 O 1.0346(4) 0.4149(8) 0.6707(4) 0.0381(15) Uani 1 1 d . U . . .
O2 O 0.8423(4) 0.2570(9) 0.7974(4) 0.0408(16) Uani 1 1 d G U . . .
H2A H 0.8536 0.3545 0.7915 0.061 Uiso 1 1 d G U . . .
H2B H 0.7823 0.2449 0.7895 0.061 Uiso 1 1 d G U . . .
C9 C 0.5218(4) -0.1016(7) 0.3844(5) 0.0138(6) Uani 1 1 d . . . . .
H9 H 0.5858 -0.1438 0.4220 0.017 Uiso 1 1 calc R U . . .
C10 C 1.1477(4) 0.1847(7) 0.6116(5) 0.0127(6) Uani 1 1 d . . . . .
H10 H 1.1502 0.2295 0.6779 0.015 Uiso 1 1 calc R U . . .
C11 C 0.5900(4) 0.3229(7) 0.4271(5) 0.0095(6) Uani 1 1 d . . . . .
C12 C 0.5079(4) 0.0629(7) 0.3714(5) 0.0138(6) Uani 1 1 d . . . . .
C13 C 0.7779(4) 0.3437(7) 0.4996(5) 0.0095(6) Uani 1 1 d . . . . .
H13 H 0.7828 0.2564 0.4570 0.011 Uiso 1 1 calc R U . . .
C14 C 0.9649(4) 0.3702(10) 0.5886(5) 0.0228(16) Uani 1 1 d . . . . .
C15 C 1.0631(4) 0.1992(7) 0.5172(5) 0.0127(6) Uani 1 1 d . . . . .
C16 C 0.8632(4) 0.4224(9) 0.5699(5) 0.0195(15) Uani 1 1 d . . . . .
C17 C 0.4120(4) 0.1201(7) 0.3151(5) 0.0138(6) Uani 1 1 d . . . . .
H17 H 0.3988 0.2301 0.3037 0.017 Uiso 1 1 calc R U . . .
C18 C 0.6862(4) 0.3986(7) 0.4948(5) 0.0095(6) Uani 1 1 d . . . . .
C19 C 0.4423(4) -0.2007(7) 0.3425(5) 0.0138(6) Uani 1 1 d . . . . .
H19 H 0.4529 -0.3116 0.3516 0.017 Uiso 1 1 calc R U . . .
C20 C 0.6821(4) 0.5268(7) 0.5564(5) 0.0095(6) Uani 1 1 d . . . . .
H20 H 0.6191 0.5636 0.5511 0.011 Uiso 1 1 calc R U . . .
C21 C 0.8500(5) 0.5480(9) 0.6292(5) 0.0190(15) Uani 1 1 d . U . . .
H21 H 0.9076 0.5991 0.6775 0.023 Uiso 1 1 calc R U . . .
C22 C 1.1477(5) 0.0448(10) 0.4278(5) 0.0227(16) Uani 1 1 d . . . . .
H22 H 1.1470 -0.0039 0.3634 0.027 Uiso 1 1 calc R U . . .
C23 C 1.2273(4) 0.1040(7) 0.6059(5) 0.0127(6) Uani 1 1 d . . . . .
H23 H 1.2849 0.0980 0.6701 0.015 Uiso 1 1 calc R U . . .
C24 C 0.3370(4) 0.0075(7) 0.2769(5) 0.0138(6) Uani 1 1 d . . . . .
H24 H 0.2718 0.0451 0.2392 0.017 Uiso 1 1 calc R U . . .
C25 C 1.0642(5) 0.1231(12) 0.4240(6) 0.033(2) Uani 1 1 d . . . . .
H25 H 1.0075 0.1258 0.3587 0.039 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
O1 C11 1.228(7) . ?
N2 C24 1.329(8) . ?
N2 C19 1.348(7) . ?
N3 C14 1.361(9) . ?
N3 C15 1.397(8) . ?
N4 C21 1.334(9) . ?
N4 C20 1.356(7) . ?
N5 C22 1.339(7) . ?
N5 C23 1.345(9) . ?
N6 C11 1.372(8) . ?
N6 C12 1.410(8) . ?
O7 C14 1.241(8) . ?
C9 C19 1.371(8) . ?
C9 C12 1.407(8) . ?
C10 C23 1.376(9) . ?
C10 C15 1.400(8) . ?
C11 C18 1.499(8) . ?
C12 C17 1.405(8) . ?
C13 C18 1.399(8) . ?
C13 C16 1.413(8) . ?
C14 C16 1.482(9) . ?
C15 C25 1.405(10) . ?
C16 C21 1.380(10) . ?
C17 C24 1.396(8) . ?
C18 C20 1.375(8) . ?
C22 C25 1.374(10) . ?

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
C24 N2 C19 117.1(5) . . ?
C14 N3 C15 127.0(5) . . ?
C21 N4 C20 116.2(6) . . ?
C22 N5 C23 115.7(5) . . ?
C11 N6 C12 126.1(5) . . ?
C19 C9 C12 119.5(5) . . ?
C23 C10 C15 118.3(6) . . ?
O1 C11 N6 123.8(5) . . ?
O1 C11 C18 120.0(5) . . ?
N6 C11 C18 116.1(5) . . ?
C17 C12 C9 118.4(5) . . ?
C17 C12 N6 123.7(5) . . ?
C9 C12 N6 117.9(5) . . ?
C18 C13 C16 117.8(6) . . ?
O7 C14 N3 123.2(6) . . ?
O7 C14 C16 119.8(6) . . ?
N3 C14 C16 116.9(5) . . ?
N3 C15 C10 124.3(6) . . ?
N3 C15 C25 118.6(5) . . ?
C10 C15 C25 117.0(6) . . ?
C21 C16 C13 117.6(6) . . ?
C21 C16 C14 118.8(6) . . ?
C13 C16 C14 123.5(6) . . ?
C24 C17 C12 116.8(5) . . ?
C20 C18 C13 119.4(5) . . ?
C20 C18 C11 117.0(5) . . ?
C13 C18 C11 123.6(5) . . ?
N2 C19 C9 123.0(6) . . ?
N4 C20 C18 123.5(6) . . ?
N4 C21 C16 125.4(6) . . ?
N5 C22 C25 124.0(6) . . ?
N5 C23 C10 125.3(5) . . ?
N2 C24 C17 125.2(5) . . ?
C22 C25 C15 119.6(6) . . ?

_refine_diff_density_max         0.790
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.182

