# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2241531'
loop_
_audit_author_name
_audit_author_address
'Lidija Radovanovic'
;Innovation Centre of the Faculty of Technology and Metallurgy, University of Belgrade
Serbia
;
_audit_update_record             
;
2023-02-13 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           'WinGX routine CIF_UPDATE'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N2 O2'
_chemical_formula_sum            'C12 H14 N2 O2'
_chemical_formula_weight         218.25

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_hall  '-P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_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'
'-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                   7.5657(15)
_cell_length_b                   11.619(2)
_cell_length_c                   25.402(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2233.0(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    18953
_cell_measurement_theta_min      2.3810
_cell_measurement_theta_max      26.2970

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89578
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            42984
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0073
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.134
_diffrn_reflns_theta_max         25.349
_reflns_number_total             2040
_reflns_number_gt                1895
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0542P)²+0.6600P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2040
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
C2 C 0.74273(17) 0.29660(12) 0.47514(5) 0.0341(3) Uani 1 1 d . . . . .
C4 C 0.84996(17) 0.43400(12) 0.41946(6) 0.0391(3) Uani 1 1 d . . . . .
C5 C 0.65156(16) 0.42153(11) 0.40846(5) 0.0334(3) Uani 1 1 d . . . . .
C6 C 0.62798(17) 0.37695(11) 0.35234(5) 0.0338(3) Uani 1 1 d . . . . .
C7 C 0.6706(2) 0.44769(13) 0.30996(6) 0.0443(4) Uani 1 1 d . . . . .
H7 H 0.709239 0.522454 0.316138 0.053 Uiso 1 1 calc R U . . .
C8 C 0.6561(2) 0.40825(15) 0.25896(6) 0.0512(4) Uani 1 1 d . . . . .
H8 H 0.686345 0.456884 0.231311 0.061 Uiso 1 1 calc R U . . .
C9 C 0.5977(2) 0.29826(15) 0.24794(6) 0.0494(4) Uani 1 1 d . . . . .
C10 C 0.5568(2) 0.22817(14) 0.29008(7) 0.0525(4) Uani 1 1 d . . . . .
H10 H 0.518157 0.153477 0.2837 0.063 Uiso 1 1 calc R U . . .
C11 C 0.57178(19) 0.26612(12) 0.34183(6) 0.0434(4) Uani 1 1 d . . . . .
H11 H 0.543886 0.216778 0.369436 0.052 Uiso 1 1 calc R U . . .
C12 C 0.5788(3) 0.2560(2) 0.19210(7) 0.0716(6) Uani 1 1 d . . . . .
H12A H 0.628499 0.1802 0.189225 0.107 Uiso 1 1 calc R U . . .
H12B H 0.639963 0.307252 0.16874 0.107 Uiso 1 1 calc R U . . .
H12C H 0.455871 0.253491 0.1828 0.107 Uiso 1 1 calc R U . . .
C13 C 0.55739(19) 0.53667(12) 0.41822(6) 0.0398(3) Uani 1 1 d . . . . .
H13A H 0.582933 0.562289 0.453763 0.048 Uiso 1 1 calc R U . . .
H13B H 0.604083 0.593806 0.394105 0.048 Uiso 1 1 calc R U . . .
C14 C 0.3591(2) 0.52923(15) 0.41117(7) 0.0518(4) Uani 1 1 d . . . . .
H14A H 0.332866 0.500137 0.37667 0.078 Uiso 1 1 calc R U . . .
H14B H 0.308203 0.60441 0.415139 0.078 Uiso 1 1 calc R U . . .
H14C H 0.310492 0.478425 0.437215 0.078 Uiso 1 1 calc R U . . .
N1 N 0.60410(14) 0.33608(10) 0.44818(4) 0.0373(3) Uani 1 1 d . . . . .
H1 H 0.497425 0.313465 0.453646 0.045 Uiso 1 1 calc R U . . .
N3 N 0.89136(15) 0.35322(10) 0.45672(5) 0.0419(3) Uani 1 1 d . . . . .
H3 H 0.997082 0.339321 0.467408 0.05 Uiso 1 1 calc R U . . .
O1 O 0.74335(12) 0.22407(9) 0.51030(4) 0.0417(3) Uani 1 1 d . . . . .
O2 O 0.94956(15) 0.50127(11) 0.39927(5) 0.0609(4) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.0296(7) 0.0368(7) 0.0358(7) 0.0050(5) 0.0021(5) 0.0021(5)
C4 0.0307(7) 0.0410(7) 0.0456(8) 0.0107(6) -0.0027(6) -0.0035(6)
C5 0.0273(7) 0.0349(7) 0.0381(7) 0.0092(5) -0.0011(5) -0.0019(5)
C6 0.0258(6) 0.0349(7) 0.0407(7) 0.0048(5) 0.0000(5) 0.0036(5)
C7 0.0476(9) 0.0409(7) 0.0443(8) 0.0047(6) 0.0033(7) -0.0020(6)
C8 0.0509(9) 0.0619(10) 0.0407(8) 0.0067(7) 0.0051(7) 0.0054(8)
C9 0.0360(8) 0.0642(10) 0.0481(8) -0.0085(8) -0.0052(6) 0.0129(7)
C10 0.0460(9) 0.0456(8) 0.0658(10) -0.0112(8) -0.0097(8) 0.0010(7)
C11 0.0402(8) 0.0378(7) 0.0521(9) 0.0051(6) -0.0037(6) -0.0014(6)
C12 0.0577(11) 0.0998(15) 0.0571(11) -0.0232(10) -0.0088(8) 0.0154(11)
C13 0.0429(8) 0.0379(7) 0.0387(7) 0.0013(6) -0.0019(6) 0.0019(6)
C14 0.0413(8) 0.0536(9) 0.0604(10) 0.0045(7) 0.0035(7) 0.0143(7)
N1 0.0257(5) 0.0446(6) 0.0417(6) 0.0143(5) 0.0002(4) -0.0027(5)
N3 0.0258(6) 0.0498(7) 0.0502(7) 0.0164(6) -0.0046(5) -0.0010(5)
O1 0.0355(5) 0.0471(6) 0.0425(5) 0.0165(5) 0.0023(4) 0.0034(4)
O2 0.0358(6) 0.0651(7) 0.0818(8) 0.0357(6) -0.0092(5) -0.0159(5)

_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
C2 O1 1.2281(16) . ?
C2 N1 1.3339(17) . ?
C2 N3 1.3842(17) . ?
C4 O2 1.2007(17) . ?
C4 N3 1.3693(18) . ?
C4 C5 1.5337(18) . ?
C5 N1 1.4604(16) . ?
C5 C6 1.5272(19) . ?
C5 C13 1.5359(19) . ?
C6 C11 1.382(2) . ?
C6 C7 1.3921(19) . ?
C7 C8 1.379(2) . ?
C7 H7 0.93 . ?
C8 C9 1.381(2) . ?
C8 H8 0.93 . ?
C9 C10 1.380(2) . ?
C9 C12 1.508(2) . ?
C10 C11 1.391(2) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 C14 1.513(2) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
N1 H1 0.86 . ?
N3 H3 0.86 . ?

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
O1 C2 N1 127.76(12) . . ?
O1 C2 N3 124.67(12) . . ?
N1 C2 N3 107.57(11) . . ?
O2 C4 N3 126.72(13) . . ?
O2 C4 C5 126.72(12) . . ?
N3 C4 C5 106.56(11) . . ?
N1 C5 C6 112.68(11) . . ?
N1 C5 C4 100.31(10) . . ?
C6 C5 C4 108.45(11) . . ?
N1 C5 C13 111.50(11) . . ?
C6 C5 C13 113.08(11) . . ?
C4 C5 C13 110.01(11) . . ?
C11 C6 C7 118.16(13) . . ?
C11 C6 C5 122.15(12) . . ?
C7 C6 C5 119.64(12) . . ?
C8 C7 C6 120.80(14) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 121.57(15) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 117.44(15) . . ?
C10 C9 C12 121.05(17) . . ?
C8 C9 C12 121.51(17) . . ?
C9 C10 C11 121.84(15) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C6 C11 C10 120.19(14) . . ?
C6 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C5 113.01(12) . . ?
C14 C13 H13A 109 . . ?
C5 C13 H13A 109 . . ?
C14 C13 H13B 109 . . ?
C5 C13 H13B 109 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 N1 C5 113.27(11) . . ?
C2 N1 H1 123.4 . . ?
C5 N1 H1 123.4 . . ?
C4 N3 C2 111.94(11) . . ?
C4 N3 H3 124 . . ?
C2 N3 H3 124 . . ?

_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2241532'
loop_
_audit_author_name
_audit_author_address
'Lidija Radovanovic'
;Innovation Centre of the Faculty of Technology and Metallurgy, University of Belgrade
Serbia
;
_audit_update_record             
;
2023-02-13 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           'WinGX routine CIF_UPDATE'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 N2 O2'
_chemical_formula_sum            'C11 H12 N2 O2'
_chemical_formula_weight         204.23

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_hall  '-P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_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'
'-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                   7.3489(15)
_cell_length_b                   14.605(3)
_cell_length_c                   19.983(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2144.8(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3601
_cell_measurement_theta_min      3.2500
_cell_measurement_theta_max      26.2900

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10971
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.789
_diffrn_reflns_theta_max         25.349
_reflns_number_total             1959
_reflns_number_gt                1473
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0471P)²+0.5968P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1959
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.109
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.05
_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
C2 C 0.0063(2) 0.49319(11) 0.33795(8) 0.0362(4) Uani 1 1 d . . . . .
C4 C 0.1879(2) 0.47742(11) 0.42975(8) 0.0329(4) Uani 1 1 d . . . . .
C5 C 0.3111(2) 0.47539(11) 0.36805(7) 0.0335(4) Uani 1 1 d . . . . .
C6 C 0.4194(2) 0.38601(11) 0.36430(8) 0.0362(4) Uani 1 1 d . . . . .
C7 C 0.5532(2) 0.36848(12) 0.41164(9) 0.0435(4) Uani 1 1 d . . . . .
H7 H 0.573746 0.411147 0.445349 0.052 Uiso 1 1 calc R U . . .
C8 C 0.6569(3) 0.28948(13) 0.41018(11) 0.0550(5) Uani 1 1 d . . . . .
C9 C 0.6265(3) 0.22756(14) 0.35939(13) 0.0689(6) Uani 1 1 d . . . . .
H9 H 0.696152 0.174506 0.356963 0.083 Uiso 1 1 calc R U . . .
C10 C 0.4945(3) 0.24345(14) 0.31248(12) 0.0738(7) Uani 1 1 d . . . . .
H10 H 0.475068 0.20067 0.278755 0.089 Uiso 1 1 calc R U . . .
C11 C 0.3891(3) 0.32242(13) 0.31437(10) 0.0552(5) Uani 1 1 d . . . . .
H11 H 0.299244 0.332313 0.282397 0.066 Uiso 1 1 calc R U . . .
C12 C 0.8002(3) 0.27157(17) 0.46296(15) 0.0867(8) Uani 1 1 d . . . . .
H12A H 0.784083 0.211139 0.480901 0.13 Uiso 1 1 calc R U . . .
H12B H 0.788532 0.315798 0.498241 0.13 Uiso 1 1 calc R U . . .
H12C H 0.91893 0.276414 0.44323 0.13 Uiso 1 1 calc R U . . .
C13 C 0.4345(2) 0.55989(12) 0.37025(10) 0.0468(5) Uani 1 1 d . . . . .
H13A H 0.508491 0.561675 0.330671 0.07 Uiso 1 1 calc R U . . .
H13B H 0.511359 0.556795 0.409032 0.07 Uiso 1 1 calc R U . . .
H13C H 0.361044 0.61416 0.372415 0.07 Uiso 1 1 calc R U . . .
N1 N 0.17590(18) 0.48344(10) 0.31540(7) 0.0412(4) Uani 1 1 d . . . . .
H1 H 0.202761 0.482046 0.273521 0.049 Uiso 1 1 calc R U . . .
N3 N 0.01572(17) 0.48769(10) 0.40755(6) 0.0391(4) Uani 1 1 d . . . . .
H3 H -0.077673 0.490518 0.433401 0.047 Uiso 1 1 calc R U . . .
O1 O -0.13345(16) 0.50553(9) 0.30664(6) 0.0513(4) Uani 1 1 d . . . . .
O2 O 0.23727(15) 0.47303(8) 0.48776(5) 0.0452(3) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.0339(9) 0.0481(10) 0.0267(9) -0.0036(7) -0.0018(7) 0.0029(7)
C4 0.0285(8) 0.0434(9) 0.0270(9) -0.0023(7) 0.0006(6) 0.0018(7)
C5 0.0288(8) 0.0466(9) 0.0252(8) -0.0005(7) 0.0017(6) 0.0019(6)
C6 0.0310(9) 0.0420(9) 0.0357(9) -0.0009(7) 0.0088(7) -0.0010(7)
C7 0.0366(9) 0.0442(10) 0.0498(11) -0.0015(8) 0.0001(8) 0.0016(8)
C8 0.0438(11) 0.0475(11) 0.0737(14) 0.0077(10) 0.0037(10) 0.0051(9)
C9 0.0676(14) 0.0459(12) 0.0931(18) -0.0007(12) 0.0088(13) 0.0156(10)
C10 0.0972(19) 0.0506(12) 0.0736(16) -0.0243(11) 0.0034(14) 0.0093(12)
C11 0.0591(12) 0.0559(12) 0.0504(12) -0.0115(10) -0.0026(9) 0.0031(10)
C12 0.0678(15) 0.0711(16) 0.121(2) 0.0144(14) -0.0248(15) 0.0215(12)
C13 0.0385(10) 0.0449(10) 0.0570(12) 0.0010(9) 0.0073(8) 0.0009(8)
N1 0.0357(8) 0.0671(10) 0.0208(7) -0.0001(6) 0.0030(6) 0.0070(7)
N3 0.0254(7) 0.0669(9) 0.0250(7) -0.0010(6) 0.0030(5) 0.0040(6)
O1 0.0377(7) 0.0804(9) 0.0357(7) -0.0066(6) -0.0110(5) 0.0095(6)
O2 0.0344(6) 0.0783(9) 0.0229(6) -0.0028(6) -0.0010(5) 0.0086(6)

_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
C2 O1 1.2158(19) . ?
C2 N1 1.333(2) . ?
C2 N3 1.395(2) . ?
C4 O2 1.2163(18) . ?
C4 N3 1.3492(19) . ?
C4 C5 1.530(2) . ?
C5 N1 1.4520(19) . ?
C5 C6 1.531(2) . ?
C5 C13 1.532(2) . ?
C6 C11 1.381(2) . ?
C6 C7 1.389(2) . ?
C7 C8 1.383(2) . ?
C7 H7 0.93 . ?
C8 C9 1.378(3) . ?
C8 C12 1.513(3) . ?
C9 C10 1.369(3) . ?
C9 H9 0.93 . ?
C10 C11 1.390(3) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
N1 H1 0.86 . ?
N3 H3 0.86 . ?

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
O1 C2 N1 129.15(15) . . ?
O1 C2 N3 124.33(14) . . ?
N1 C2 N3 106.52(13) . . ?
O2 C4 N3 126.79(14) . . ?
O2 C4 C5 126.19(14) . . ?
N3 C4 C5 106.99(13) . . ?
N1 C5 C4 100.22(11) . . ?
N1 C5 C6 112.91(13) . . ?
C4 C5 C6 111.31(13) . . ?
N1 C5 C13 111.14(13) . . ?
C4 C5 C13 108.16(13) . . ?
C6 C5 C13 112.38(13) . . ?
C11 C6 C7 118.83(16) . . ?
C11 C6 C5 121.68(15) . . ?
C7 C6 C5 119.48(14) . . ?
C8 C7 C6 122.00(17) . . ?
C8 C7 H7 119 . . ?
C6 C7 H7 119 . . ?
C9 C8 C7 118.26(19) . . ?
C9 C8 C12 120.87(19) . . ?
C7 C8 C12 120.87(19) . . ?
C10 C9 C8 120.56(19) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 121.1(2) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C6 C11 C10 119.19(19) . . ?
C6 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 N1 C5 113.80(13) . . ?
C2 N1 H1 123.1 . . ?
C5 N1 H1 123.1 . . ?
C4 N3 C2 112.40(13) . . ?
C4 N3 H3 123.8 . . ?
C2 N3 H3 123.8 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.176
_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_3
_database_code_depnum_ccdc_archive 'CCDC 2241533'
loop_
_audit_author_name
_audit_author_address
'Lidija Radovanovic'
;Innovation Centre of the Faculty of Technology and Metallurgy, University of Belgrade
Serbia
;
_audit_update_record             
;
2023-02-13 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           'WinGX routine CIF_UPDATE'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 N2 O3'
_chemical_formula_sum            'C11 H12 N2 O3'
_chemical_formula_weight         220.23
_chemical_absolute_configuration unk

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_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                   6.2259(12)
_cell_length_b                   7.1884(14)
_cell_length_c                   23.607(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1056.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3359
_cell_measurement_theta_min      2.9570
_cell_measurement_theta_max      28.1300

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.99506
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7319
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.962
_diffrn_reflns_theta_max         25.326
_reflns_number_total             1940
_reflns_number_gt                1773
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0380P)²+0.1469P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1940
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
C2 C 0.7344(4) 0.4492(3) 0.54148(9) 0.0294(5) Uani 1 1 d . . . . .
C4 C 0.4518(3) 0.6094(3) 0.57806(8) 0.0278(5) Uani 1 1 d . . . . .
C5 C 0.6572(3) 0.7107(3) 0.59647(9) 0.0259(5) Uani 1 1 d . . . . .
C6 C 0.6819(3) 0.7143(3) 0.66100(8) 0.0256(5) Uani 1 1 d . . . . .
C7 C 0.5229(4) 0.7935(3) 0.69454(10) 0.0386(6) Uani 1 1 d . . . . .
H7 H 0.399712 0.840485 0.677469 0.046 Uiso 1 1 calc R U . . .
C8 C 0.5438(4) 0.8037(4) 0.75223(10) 0.0428(6) Uani 1 1 d . . . . .
H8 H 0.434943 0.857077 0.773772 0.051 Uiso 1 1 calc R U . . .
C9 C 0.7256(4) 0.7352(3) 0.77866(9) 0.0344(5) Uani 1 1 d . . . . .
C10 C 0.8864(4) 0.6568(3) 0.74644(10) 0.0361(5) Uani 1 1 d . . . . .
H10 H 1.009705 0.610817 0.763709 0.043 Uiso 1 1 calc R U . . .
C11 C 0.8631(3) 0.6470(3) 0.68791(9) 0.0312(5) Uani 1 1 d . . . . .
H11 H 0.972059 0.593813 0.666372 0.037 Uiso 1 1 calc R U . . .
C12 C 0.9051(5) 0.6698(4) 0.86579(11) 0.0545(7) Uani 1 1 d . . . . .
H12A H 1.035783 0.728926 0.853892 0.082 Uiso 1 1 calc R U . . .
H12B H 0.912338 0.539217 0.857496 0.082 Uiso 1 1 calc R U . . .
H12C H 0.886397 0.68713 0.905813 0.082 Uiso 1 1 calc R U . . .
C13 C 0.6552(4) 0.9066(3) 0.57136(10) 0.0390(6) Uani 1 1 d . . . . .
H13A H 0.6276 0.899511 0.531405 0.059 Uiso 1 1 calc R U . . .
H13B H 0.791982 0.964661 0.577632 0.059 Uiso 1 1 calc R U . . .
H13C H 0.544617 0.978837 0.589262 0.059 Uiso 1 1 calc R U . . .
N1 N 0.8179(3) 0.5939(3) 0.56898(7) 0.0322(5) Uani 1 1 d . . . . .
H1 H 0.953453 0.616333 0.570398 0.039 Uiso 1 1 calc R U . . .
N3 N 0.5123(3) 0.4599(3) 0.54747(7) 0.0327(5) Uani 1 1 d . . . . .
H3 H 0.424052 0.380501 0.533312 0.039 Uiso 1 1 calc R U . . .
O1 O 0.8284(3) 0.3290(2) 0.51517(7) 0.0455(5) Uani 1 1 d . . . . .
O2 O 0.2687(2) 0.6618(3) 0.58716(7) 0.0429(4) Uani 1 1 d . . . . .
O3 O 0.7288(3) 0.7498(3) 0.83649(7) 0.0522(5) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.0291(11) 0.0335(12) 0.0256(12) -0.0035(9) 0.0013(9) 0.0039(9)
C4 0.0228(10) 0.0364(13) 0.0240(11) -0.0028(9) 0.0005(8) -0.0024(9)
C5 0.0204(10) 0.0300(11) 0.0274(11) -0.0060(9) -0.0008(8) -0.0023(9)
C6 0.0244(10) 0.0241(10) 0.0283(11) -0.0054(8) -0.0006(8) -0.0006(8)
C7 0.0371(12) 0.0461(14) 0.0326(13) -0.0066(11) -0.0055(10) 0.0187(11)
C8 0.0491(14) 0.0488(16) 0.0306(13) -0.0079(11) 0.0024(11) 0.0192(12)
C9 0.0455(13) 0.0323(12) 0.0254(12) -0.0042(9) -0.0046(10) 0.0026(10)
C10 0.0314(11) 0.0419(13) 0.0349(13) 0.0002(11) -0.0109(10) 0.0017(11)
C11 0.0251(10) 0.0374(12) 0.0310(12) -0.0036(10) 0.0014(9) 0.0018(9)
C12 0.0682(19) 0.0631(18) 0.0321(14) 0.0024(13) -0.0170(12) 0.0000(15)
C13 0.0466(14) 0.0370(13) 0.0334(13) 0.0023(10) -0.0042(11) -0.0039(12)
N1 0.0173(8) 0.0462(12) 0.0331(10) -0.0146(9) 0.0019(7) 0.0000(8)
N3 0.0281(10) 0.0346(11) 0.0353(11) -0.0115(8) -0.0006(8) -0.0075(8)
O1 0.0452(10) 0.0450(10) 0.0462(10) -0.0171(8) 0.0060(8) 0.0090(8)
O2 0.0202(8) 0.0605(11) 0.0481(10) -0.0149(9) 0.0003(7) 0.0028(7)
O3 0.0678(12) 0.0626(12) 0.0261(9) -0.0070(8) -0.0095(8) 0.0165(10)

_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
C2 O1 1.215(3) . ?
C2 N1 1.332(3) . ?
C2 N3 1.392(3) . ?
C4 O2 1.220(2) . ?
C4 N3 1.349(3) . ?
C4 C5 1.534(3) . ?
C5 N1 1.458(3) . ?
C5 C13 1.529(3) . ?
C5 C6 1.531(3) . ?
C6 C11 1.382(3) . ?
C6 C7 1.390(3) . ?
C7 C8 1.370(3) . ?
C7 H7 0.93 . ?
C8 C9 1.383(3) . ?
C8 H8 0.93 . ?
C9 O3 1.369(3) . ?
C9 C10 1.378(3) . ?
C10 C11 1.391(3) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 O3 1.419(3) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
N1 H1 0.86 . ?
N3 H3 0.86 . ?

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
O1 C2 N1 128.1(2) . . ?
O1 C2 N3 124.7(2) . . ?
N1 C2 N3 107.15(18) . . ?
O2 C4 N3 127.0(2) . . ?
O2 C4 C5 125.6(2) . . ?
N3 C4 C5 107.29(16) . . ?
N1 C5 C13 111.31(18) . . ?
N1 C5 C6 112.55(17) . . ?
C13 C5 C6 111.77(17) . . ?
N1 C5 C4 99.95(15) . . ?
C13 C5 C4 108.69(18) . . ?
C6 C5 C4 111.96(17) . . ?
C11 C6 C7 117.57(19) . . ?
C11 C6 C5 122.24(18) . . ?
C7 C6 C5 120.15(18) . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 120.5(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
O3 C9 C10 124.8(2) . . ?
O3 C9 C8 115.7(2) . . ?
C10 C9 C8 119.4(2) . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C6 C11 C10 121.6(2) . . ?
C6 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 N1 C5 113.50(17) . . ?
C2 N1 H1 123.3 . . ?
C5 N1 H1 123.3 . . ?
C4 N3 C2 112.08(18) . . ?
C4 N3 H3 124 . . ?
C2 N3 H3 124 . . ?
C9 O3 C12 117.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_refine_ls_abs_structure_details 
;
 Flack x determined using 660 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.133(1)
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2241534'
loop_
_audit_author_name
_audit_author_address
'Lidija Radovanovic'
;Innovation Centre of the Faculty of Technology and Metallurgy, University of Belgrade
Serbia
;
_audit_update_record             
;
2023-02-13 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           'WinGX routine CIF_UPDATE'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N3 O4, H2 O'
_chemical_formula_sum            'C10 H11 N3 O5'
_chemical_formula_weight         253.22

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'


_cell_length_a                   6.8817(14)
_cell_length_b                   8.3267(17)
_cell_length_c                   10.789(2)
_cell_angle_alpha                83.96(3)
_cell_angle_beta                 76.71(3)
_cell_angle_gamma                70.02(3)
_cell_volume                     565.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1175
_cell_measurement_theta_min      3.1900
_cell_measurement_theta_max      28.3730

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3865
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.604
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2062
_reflns_number_gt                1592
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SIR-2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0410P)²+0.1495P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2062
_refine_ls_number_parameters     170
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.03
_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
C2 C 0.6942(3) 0.1421(2) 0.05881(19) 0.0419(5) Uani 1 1 d . . . . .
C4 C 0.6926(3) 0.0865(2) 0.27075(18) 0.0338(4) Uani 1 1 d . . . . .
C5 C 0.4635(3) 0.1816(2) 0.25678(17) 0.0337(4) Uani 1 1 d . . . . .
C6 C 0.3684(3) 0.3441(2) 0.33296(17) 0.0313(4) Uani 1 1 d . . . . .
C7 C 0.3342(3) 0.3320(2) 0.46472(18) 0.0322(4) Uani 1 1 d . . . . .
H7 H 0.368412 0.225671 0.506521 0.039 Uiso 1 1 calc R U . . .
C8 C 0.2486(3) 0.4802(2) 0.53314(18) 0.0327(4) Uani 1 1 d . . . . .
C9 C 0.1933(3) 0.6408(2) 0.4765(2) 0.0393(5) Uani 1 1 d . . . . .
H9 H 0.136674 0.738414 0.524854 0.047 Uiso 1 1 calc R U . . .
C10 C 0.2248(3) 0.6517(2) 0.3459(2) 0.0438(5) Uani 1 1 d . . . . .
H10 H 0.186396 0.758361 0.304853 0.053 Uiso 1 1 calc R U . . .
C11 C 0.3129(3) 0.5059(2) 0.27477(19) 0.0392(5) Uani 1 1 d . . . . .
H11 H 0.335556 0.516032 0.186364 0.047 Uiso 1 1 calc R U . . .
C13 C 0.3332(3) 0.0609(2) 0.2971(2) 0.0442(5) Uani 1 1 d . . . . .
H13A H 0.191507 0.118371 0.285345 0.066 Uiso 1 1 calc R U . . .
H13B H 0.330533 0.027494 0.385249 0.066 Uiso 1 1 calc R U . . .
H13C H 0.396015 -0.038829 0.246028 0.066 Uiso 1 1 calc R U . . .
N1 N 0.4946(3) 0.2157(2) 0.11942(15) 0.0416(4) Uani 1 1 d . . . . .
H1 H 0.395154 0.276519 0.081571 0.05 Uiso 1 1 calc R U . . .
N3 N 0.8130(3) 0.0683(2) 0.15079(15) 0.0413(4) Uani 1 1 d . . . . .
H3 H 0.94735 0.017032 0.133742 0.05 Uiso 1 1 calc R U . . .
N4 N 0.2155(3) 0.4647(2) 0.67218(16) 0.0409(4) Uani 1 1 d . . . . .
O1 O 0.7640(2) 0.1389(2) -0.05618(14) 0.0611(5) Uani 1 1 d . . . . .
O2 O 0.7525(2) 0.03561(17) 0.36900(13) 0.0429(4) Uani 1 1 d . . . . .
O3 O 0.1448(3) 0.59526(19) 0.73375(15) 0.0615(5) Uani 1 1 d . . . . .
O4 O 0.2593(3) 0.3214(2) 0.72219(14) 0.0639(5) Uani 1 1 d . . . . .
O5 O 0.1443(3) 0.3146(3) -0.0033(2) 0.0975(7) Uani 1 1 d D . . . .
H14 H 0.170(6) 0.327(5) -0.0819(11) 0.146 Uiso 1 1 d D U . . .
H15 H 0.022(3) 0.3425(10) 0.036(3) 0.146 Uiso 1 1 d D U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.0478(12) 0.0409(11) 0.0291(11) -0.0025(9) -0.0044(10) -0.0065(9)
C4 0.0383(11) 0.0290(9) 0.0314(11) -0.0036(8) -0.0033(9) -0.0094(8)
C5 0.0371(10) 0.0354(10) 0.0242(10) -0.0019(8) -0.0046(8) -0.0073(8)
C6 0.0272(9) 0.0347(10) 0.0312(11) -0.0013(8) -0.0034(8) -0.0107(8)
C7 0.0301(10) 0.0304(9) 0.0340(11) -0.0007(8) -0.0067(8) -0.0073(8)
C8 0.0272(9) 0.0372(10) 0.0337(11) -0.0059(8) -0.0037(8) -0.0109(8)
C9 0.0343(11) 0.0320(10) 0.0506(13) -0.0096(9) -0.0063(9) -0.0088(8)
C10 0.0478(12) 0.0315(10) 0.0506(14) 0.0049(9) -0.0100(10) -0.0132(9)
C11 0.0405(11) 0.0417(11) 0.0340(11) 0.0035(9) -0.0062(9) -0.0141(9)
C13 0.0466(12) 0.0420(11) 0.0442(13) -0.0098(9) -0.0048(10) -0.0152(9)
N1 0.0395(10) 0.0485(10) 0.0262(9) -0.0012(7) -0.0070(7) -0.0010(8)
N3 0.0342(9) 0.0494(10) 0.0306(9) -0.0039(8) -0.0029(7) -0.0030(7)
N4 0.0381(9) 0.0442(10) 0.0390(10) -0.0098(8) -0.0053(8) -0.0109(8)
O1 0.0556(10) 0.0767(11) 0.0272(9) -0.0012(7) 0.0011(7) 0.0018(8)
O2 0.0466(8) 0.0442(8) 0.0326(8) -0.0007(6) -0.0115(7) -0.0062(6)
O3 0.0769(12) 0.0536(10) 0.0465(10) -0.0231(8) -0.0017(8) -0.0128(8)
O4 0.0956(13) 0.0485(10) 0.0380(9) -0.0013(7) -0.0159(9) -0.0101(9)
O5 0.0713(14) 0.1452(19) 0.0565(13) -0.0040(14) -0.0136(11) -0.0104(13)

_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
C2 O1 1.223(2) . ?
C2 N1 1.336(3) . ?
C2 N3 1.390(3) . ?
C4 O2 1.208(2) . ?
C4 N3 1.359(2) . ?
C4 C5 1.538(3) . ?
C5 N1 1.459(2) . ?
C5 C6 1.522(3) . ?
C5 C13 1.532(3) . ?
C6 C7 1.385(3) . ?
C6 C11 1.391(3) . ?
C7 C8 1.382(3) . ?
C7 H7 0.93 . ?
C8 C9 1.376(3) . ?
C8 N4 1.463(2) . ?
C9 C10 1.374(3) . ?
C9 H9 0.93 . ?
C10 C11 1.382(3) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
N1 H1 0.86 . ?
N3 H3 0.86 . ?
N4 O4 1.224(2) . ?
N4 O3 1.225(2) . ?
O5 H14 0.829(10) . ?
O5 H15 0.819(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
O1 C2 N1 127.4(2) . . ?
O1 C2 N3 125.07(19) . . ?
N1 C2 N3 107.54(17) . . ?
O2 C4 N3 126.96(18) . . ?
O2 C4 C5 126.62(17) . . ?
N3 C4 C5 106.41(16) . . ?
N1 C5 C6 112.83(15) . . ?
N1 C5 C13 110.56(16) . . ?
C6 C5 C13 111.78(15) . . ?
N1 C5 C4 100.73(15) . . ?
C6 C5 C4 111.17(16) . . ?
C13 C5 C4 109.22(15) . . ?
C7 C6 C11 118.41(17) . . ?
C7 C6 C5 119.39(16) . . ?
C11 C6 C5 122.20(17) . . ?
C8 C7 C6 119.02(17) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C9 C8 C7 123.00(19) . . ?
C9 C8 N4 118.81(17) . . ?
C7 C8 N4 118.19(17) . . ?
C10 C9 C8 117.64(18) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C9 C10 C11 120.67(19) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C6 121.24(19) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 N1 C5 112.71(17) . . ?
C2 N1 H1 123.6 . . ?
C5 N1 H1 123.6 . . ?
C4 N3 C2 112.28(16) . . ?
C4 N3 H3 123.9 . . ?
C2 N3 H3 123.9 . . ?
O4 N4 O3 122.71(18) . . ?
O4 N4 C8 118.47(16) . . ?
O3 N4 C8 118.81(17) . . ?
H14 O5 H15 120(4) . . ?

_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.038

# END of CIF
