# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_1-trans
_database_code_depnum_ccdc_archive 'CCDC 2165095'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2022-04-07 deposited with the CCDC.	2022-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N3 O3'
_chemical_formula_sum            'C10 H9 N3 O3'
_chemical_formula_weight         219.20

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      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                   6.3645(7)
_cell_length_b                   7.7209(6)
_cell_length_c                   11.7329(11)
_cell_angle_alpha                94.916(7)
_cell_angle_beta                 97.452(8)
_cell_angle_gamma                113.275(9)
_cell_volume                     519.19(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1910
_cell_measurement_theta_min      3.8230
_cell_measurement_theta_max      74.9580

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.900
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59071
_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.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            3967
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.843
_diffrn_reflns_theta_max         76.073
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2098
_reflns_number_gt                1720
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0516P)²+0.0641P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2098
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1083
_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
C4A C -0.2386(4) 0.2194(3) 0.59773(19) 0.0827(6) Uani 1 1 d . . . . .
H6A H -0.150620 0.195112 0.662394 0.124 Uiso 1 1 calc R U . . .
H4A H -0.401437 0.145714 0.595086 0.124 Uiso 1 1 calc R U . . .
H5A H -0.207128 0.352589 0.606572 0.124 Uiso 1 1 calc R U . . .
O2A O -0.1736(2) 0.16681(19) 0.49164(11) 0.0731(4) Uani 1 1 d . . . . .
C1A C 0.0474(3) 0.2565(2) 0.48082(15) 0.0609(4) Uani 1 1 d . . . . .
O1A O 0.1927(3) 0.3727(2) 0.55626(13) 0.0929(5) Uani 1 1 d . . . . .
C2A C 0.0847(3) 0.1969(2) 0.36608(15) 0.0608(4) Uani 1 1 d . . . . .
H2A H -0.038805 0.103109 0.314014 0.073 Uiso 1 1 calc R U . . .
C3A C 0.2881(3) 0.2728(2) 0.33546(14) 0.0570(4) Uani 1 1 d . . . . .
H3A H 0.413954 0.365681 0.386730 0.068 Uiso 1 1 calc R U . . .
O1H O 0.3135(2) 0.21256(16) 0.22516(10) 0.0636(3) Uani 1 1 d . . . . .
N1H N 0.5146(2) 0.33500(19) 0.19511(12) 0.0544(3) Uani 1 1 d . . . . .
N2H N 0.6834(3) 0.2766(2) 0.18348(15) 0.0679(4) Uani 1 1 d . . . . .
N3H N 0.8450(3) 0.4111(2) 0.14459(16) 0.0716(4) Uani 1 1 d . . . . .
C1H C 0.5596(3) 0.5087(2) 0.16284(12) 0.0474(3) Uani 1 1 d . . . . .
C2H C 0.7756(3) 0.5569(2) 0.13134(14) 0.0534(4) Uani 1 1 d . . . . .
C3H C 0.8860(3) 0.7325(3) 0.09343(16) 0.0641(4) Uani 1 1 d . . . . .
H3H H 1.030007 0.767253 0.070687 0.077 Uiso 1 1 calc R U . . .
C4H C 0.7735(3) 0.8500(2) 0.09130(16) 0.0645(4) Uani 1 1 d . . . . .
H4H H 0.843733 0.968453 0.067728 0.077 Uiso 1 1 calc R U . . .
C5H C 0.5545(3) 0.7976(2) 0.12367(17) 0.0638(4) Uani 1 1 d . . . . .
H5H H 0.484221 0.882623 0.120989 0.077 Uiso 1 1 calc R U . . .
C6H C 0.4411(3) 0.6259(2) 0.15897(15) 0.0578(4) Uani 1 1 d . . . . .
H6H H 0.294662 0.590062 0.179037 0.069 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
C4A O2A 1.437(2) . ?
O2A C1A 1.328(2) . ?
C1A O1A 1.200(2) . ?
C1A C2A 1.464(3) . ?
C2A C3A 1.306(2) . ?
C3A O1H 1.388(2) . ?
O1H N1H 1.3689(17) . ?
N1H N2H 1.337(2) . ?
N1H C1H 1.355(2) . ?
N2H N3H 1.305(2) . ?
N3H C2H 1.376(2) . ?
C1H C2H 1.384(2) . ?
C1H C6H 1.389(2) . ?
C2H C3H 1.401(2) . ?
C3H C4H 1.359(3) . ?
C4H C5H 1.403(3) . ?
C5H C6H 1.365(2) . ?

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
C1A O2A C4A 117.25(15) . . ?
O1A C1A O2A 123.05(18) . . ?
O1A C1A C2A 125.82(18) . . ?
O2A C1A C2A 111.12(15) . . ?
C3A C2A C1A 121.26(16) . . ?
C2A C3A O1H 118.94(15) . . ?
N1H O1H C3A 111.98(12) . . ?
N2H N1H C1H 112.89(13) . . ?
N2H N1H O1H 119.20(14) . . ?
C1H N1H O1H 127.55(13) . . ?
N3H N2H N1H 107.25(14) . . ?
N2H N3H C2H 108.25(14) . . ?
N1H C1H C2H 102.28(13) . . ?
N1H C1H C6H 134.18(15) . . ?
C2H C1H C6H 123.54(15) . . ?
N3H C2H C1H 109.33(14) . . ?
N3H C2H C3H 130.82(16) . . ?
C1H C2H C3H 119.86(15) . . ?
C4H C3H C2H 117.14(16) . . ?
C3H C4H C5H 121.83(16) . . ?
C6H C5H C4H 122.27(17) . . ?
C5H C6H C1H 115.34(16) . . ?

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.157
_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_1-cis
_database_code_depnum_ccdc_archive 'CCDC 2165096'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2022-04-07 deposited with the CCDC.	2022-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N3 O3'
_chemical_formula_sum            'C10 H9 N3 O3'
_chemical_formula_weight         219.20

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                   7.5550(2)
_cell_length_b                   18.3095(5)
_cell_length_c                   7.8064(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.678(3)
_cell_angle_gamma                90
_cell_volume                     1039.67(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    246(15)
_cell_measurement_reflns_used    2385
_cell_measurement_theta_min      4.8310
_cell_measurement_theta_max      75.6400

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.899
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88028
_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.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      246(15)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            4916
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.831
_diffrn_reflns_theta_max         75.705
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2132
_reflns_number_gt                1819
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0701P)²+0.0769P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2132
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1335
_refine_ls_wR_factor_gt          0.1244
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
C4A C 0.8794(3) -0.09717(10) 0.4581(3) 0.0833(5) Uani 1 1 d . . . . .
H6A H 0.780813 -0.131178 0.414166 0.125 Uiso 1 1 calc R U . . .
H4A H 0.963363 -0.116692 0.563103 0.125 Uiso 1 1 calc R U . . .
H5A H 0.942986 -0.089048 0.368660 0.125 Uiso 1 1 calc R U . . .
O2A O 0.80590(16) -0.02920(7) 0.50038(15) 0.0740(3) Uani 1 1 d . . . . .
C1A C 0.6849(2) 0.00307(9) 0.3636(2) 0.0642(4) Uani 1 1 d . . . . .
O1A O 0.6387(2) -0.02298(9) 0.21876(18) 0.1034(5) Uani 1 1 d . . . . .
C2A C 0.6218(2) 0.07274(10) 0.4185(2) 0.0731(4) Uani 1 1 d . . . . .
H2A H 0.675795 0.088422 0.534127 0.088 Uiso 1 1 calc R U . . .
C3A C 0.4946(2) 0.11491(10) 0.3169(2) 0.0710(4) Uani 1 1 d . . . . .
H3A H 0.464912 0.159058 0.361153 0.085 Uiso 1 1 calc R U . . .
O1H O 0.40574(18) 0.09426(7) 0.14662(17) 0.0813(4) Uani 1 1 d . . . . .
N1H N 0.29028(18) 0.14776(7) 0.05665(19) 0.0689(4) Uani 1 1 d . . . . .
N2H N 0.3580(2) 0.20419(9) -0.0142(3) 0.0843(5) Uani 1 1 d . . . . .
N3H N 0.2190(2) 0.24090(8) -0.1110(2) 0.0821(4) Uani 1 1 d . . . . .
C1H C 0.1043(2) 0.14456(8) 0.00375(19) 0.0578(3) Uani 1 1 d . . . . .
C2H C 0.0601(2) 0.20597(8) -0.1038(2) 0.0634(4) Uani 1 1 d . . . . .
C3H C -0.1243(3) 0.22254(10) -0.1863(2) 0.0750(4) Uani 1 1 d . . . . .
H3H H -0.156962 0.263404 -0.258677 0.090 Uiso 1 1 calc R U . . .
C4H C -0.2537(2) 0.17617(12) -0.1558(2) 0.0792(5) Uani 1 1 d . . . . .
H4H H -0.377239 0.185878 -0.208874 0.095 Uiso 1 1 calc R U . . .
C5H C -0.2065(2) 0.11420(11) -0.0470(2) 0.0773(5) Uani 1 1 d . . . . .
H5H H -0.299645 0.084036 -0.030661 0.093 Uiso 1 1 calc R U . . .
C6H C -0.0275(2) 0.09686(9) 0.0359(2) 0.0670(4) Uani 1 1 d . . . . .
H6H H 0.004193 0.056055 0.108697 0.080 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
C4A O2A 1.437(2) . ?
O2A C1A 1.341(2) . ?
C1A O1A 1.189(2) . ?
C1A C2A 1.466(2) . ?
C2A C3A 1.318(3) . ?
C3A O1H 1.371(2) . ?
O1H N1H 1.3720(18) . ?
N1H N2H 1.337(2) . ?
N1H C1H 1.355(2) . ?
N2H N3H 1.303(2) . ?
N3H C2H 1.375(2) . ?
C1H C2H 1.389(2) . ?
C1H C6H 1.397(2) . ?
C2H C3H 1.400(2) . ?
C3H C4H 1.364(3) . ?
C4H C5H 1.405(3) . ?
C5H C6H 1.369(3) . ?

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
C1A O2A C4A 114.90(13) . . ?
O1A C1A O2A 122.84(15) . . ?
O1A C1A C2A 126.29(16) . . ?
O2A C1A C2A 110.87(14) . . ?
C3A C2A C1A 125.16(16) . . ?
C2A C3A O1H 120.56(14) . . ?
C3A O1H N1H 112.12(12) . . ?
N2H N1H C1H 112.88(14) . . ?
N2H N1H O1H 120.12(14) . . ?
C1H N1H O1H 126.07(13) . . ?
N3H N2H N1H 107.43(14) . . ?
N2H N3H C2H 108.22(14) . . ?
N1H C1H C2H 102.10(13) . . ?
N1H C1H C6H 134.68(15) . . ?
C2H C1H C6H 123.23(15) . . ?
N3H C2H C1H 109.35(15) . . ?
N3H C2H C3H 130.63(16) . . ?
C1H C2H C3H 120.01(15) . . ?
C4H C3H C2H 117.12(17) . . ?
C3H C4H C5H 122.10(17) . . ?
C6H C5H C4H 122.02(16) . . ?
C5H C6H C1H 115.52(16) . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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 2165098'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2022-04-07 deposited with the CCDC.	2022-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 O6'
_chemical_formula_sum            'C12 H12 O6'
_chemical_formula_weight         252.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   18.1583(4)
_cell_length_b                   10.1532(2)
_cell_length_c                   26.4824(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.542(2)
_cell_angle_gamma                90
_cell_volume                     4726.01(17)
_cell_formula_units_Z            16
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5165
_cell_measurement_theta_min      5.0090
_cell_measurement_theta_max      75.1140

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             2112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.985
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.53626
_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.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            12047
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.448
_diffrn_reflns_theta_max         75.827
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4825
_reflns_number_gt                4221
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0718P)²+3.2261P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4825
_refine_ls_number_parameters     347
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1377
_refine_ls_wR_factor_gt          0.1324
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
C4A1 C 0.66172(13) -0.0715(2) 0.17498(9) 0.0429(6) Uani 0.796(4) 1 d D . P A 1
H6A1 H 0.672443 -0.127384 0.205185 0.064 Uiso 0.796(4) 1 calc R U P A 1
H4A1 H 0.707078 -0.025089 0.173231 0.064 Uiso 0.796(4) 1 calc R U P A 1
H5A1 H 0.644482 -0.124202 0.144171 0.064 Uiso 0.796(4) 1 calc R U P A 1
O2A1 O 0.6030(3) 0.0226(6) 0.1785(3) 0.0375(5) Uani 0.796(4) 1 d D . P A 1
O1A1 O 0.5282(3) -0.1529(4) 0.1771(3) 0.0491(6) Uani 0.796(4) 1 d D . P A 1
C1A1 C 0.53675(10) -0.0373(2) 0.17904(6) 0.0426(4) Uani 1 1 d . . . . .
C4A7 C 0.5975(5) -0.2115(9) 0.1771(4) 0.047(2) Uani 0.204(4) 1 d D . P A 2
H4A7 H 0.596985 -0.305992 0.175612 0.070 Uiso 0.204(4) 1 calc R U P A 2
H6A7 H 0.612443 -0.176895 0.147463 0.070 Uiso 0.204(4) 1 calc R U P A 2
H5A7 H 0.633025 -0.183178 0.208556 0.070 Uiso 0.204(4) 1 calc R U P A 2
O2A7 O 0.5241(12) -0.165(2) 0.1768(11) 0.056 Uiso 0.204(4) 1 d D U P A 2
O1A7 O 0.5958(16) 0.018(3) 0.1781(14) 0.056 Uiso 0.204(4) 1 d D U P A 2
C2A1 C 0.47544(9) 0.05727(16) 0.18346(6) 0.0327(3) Uani 1 1 d . . . . .
C3A1 C 0.40574(9) 0.00490(15) 0.18642(6) 0.0321(3) Uani 1 1 d . . . . .
H3A1 H 0.398700 -0.085883 0.185481 0.038 Uiso 1 1 calc R U . . .
C4A2 C 0.19204(11) -0.1508(2) 0.18696(8) 0.0498(5) Uani 1 1 d . . . . .
H6A2 H 0.170404 -0.109475 0.212509 0.075 Uiso 1 1 calc R U . . .
H4A2 H 0.197149 -0.243633 0.193799 0.075 Uiso 1 1 calc R U . . .
H5A2 H 0.159386 -0.136549 0.152793 0.075 Uiso 1 1 calc R U . . .
O2A2 O 0.26631(7) -0.09446(12) 0.18963(5) 0.0409(3) Uani 1 1 d . . . . .
C1A2 C 0.27015(9) 0.03645(16) 0.19224(6) 0.0345(3) Uani 1 1 d . . . . .
O1A2 O 0.21791(7) 0.10672(13) 0.19489(6) 0.0509(3) Uani 1 1 d . . . . .
C2A2 C 0.34682(9) 0.08741(15) 0.19075(6) 0.0308(3) Uani 1 1 d . . . . .
C3A2 C 0.35737(9) 0.22354(15) 0.19236(6) 0.0303(3) Uani 1 1 d . . . . .
H3A2 H 0.318020 0.279079 0.195471 0.036 Uiso 1 1 calc R U . . .
C4A3 C 0.39225(12) 0.62943(17) 0.20584(9) 0.0519(5) Uani 1 1 d . . . . .
H6A3 H 0.420548 0.645538 0.241099 0.078 Uiso 1 1 calc R U . . .
H4A3 H 0.343748 0.672562 0.199615 0.078 Uiso 1 1 calc R U . . .
H5A3 H 0.419960 0.663236 0.182192 0.078 Uiso 1 1 calc R U . . .
O2A3 O 0.38089(7) 0.48883(11) 0.19772(5) 0.0408(3) Uani 1 1 d . . . . .
C1A3 C 0.44095(9) 0.42120(16) 0.19150(6) 0.0344(3) Uani 1 1 d . . . . .
O1A3 O 0.50054(8) 0.46939(13) 0.18831(5) 0.0452(3) Uani 1 1 d . . . . .
C2A3 C 0.42676(9) 0.27603(15) 0.18930(6) 0.0311(3) Uani 1 1 d . . . . .
C3A3 C 0.48579(9) 0.19304(16) 0.18456(5) 0.0325(3) Uani 1 1 d . . . . .
H3A3 H 0.532028 0.228393 0.182130 0.039 Uiso 1 1 calc R U . . .
C4A4 C 0.57702(9) 0.18936(17) 0.05111(7) 0.0392(4) Uani 1 1 d . . . . .
H6A4 H 0.597531 0.139724 0.082334 0.059 Uiso 1 1 calc R U . . .
H4A4 H 0.611578 0.258923 0.048299 0.059 Uiso 1 1 calc R U . . .
H5A4 H 0.570068 0.132393 0.021355 0.059 Uiso 1 1 calc R U . . .
O2A4 O 0.50425(6) 0.24540(11) 0.05316(4) 0.0336(3) Uani 1 1 d . . . . .
C1A4 C 0.45028(8) 0.15842(14) 0.05578(5) 0.0286(3) Uani 1 1 d . . . . .
O1A4 O 0.45870(7) 0.04083(11) 0.05608(5) 0.0377(3) Uani 1 1 d . . . . .
C2A4 C 0.37818(8) 0.22482(14) 0.05924(5) 0.0264(3) Uani 1 1 d . . . . .
C3A4 C 0.31611(8) 0.14668(14) 0.06106(5) 0.0279(3) Uani 1 1 d . . . . .
H3A4 H 0.320159 0.055481 0.059879 0.034 Uiso 1 1 calc R U . . .
C4A5 C 0.05660(11) 0.1063(2) 0.07525(10) 0.0621(6) Uani 1 1 d . . . . .
H6A5 H 0.046246 0.037507 0.049559 0.093 Uiso 1 1 calc R U . . .
H4A5 H 0.012904 0.162509 0.070609 0.093 Uiso 1 1 calc R U . . .
H5A5 H 0.067820 0.068128 0.109499 0.093 Uiso 1 1 calc R U . . .
O2A5 O 0.12113(6) 0.18269(13) 0.06933(5) 0.0421(3) Uani 1 1 d . . . . .
C1A5 C 0.18335(9) 0.11498(16) 0.06728(6) 0.0333(3) Uani 1 1 d . . . . .
O1A5 O 0.18766(7) -0.00364(12) 0.06776(5) 0.0449(3) Uani 1 1 d . . . . .
C2A5 C 0.24798(8) 0.20369(15) 0.06464(5) 0.0283(3) Uani 1 1 d . . . . .
C3A5 C 0.24209(8) 0.33997(15) 0.06605(5) 0.0290(3) Uani 1 1 d . . . . .
H3A5 H 0.196430 0.378735 0.067881 0.035 Uiso 1 1 calc R U . . .
C4A6 C 0.35077(10) 0.77316(16) 0.06947(8) 0.0417(4) Uani 1 1 d . . . . .
H6A6 H 0.324269 0.802700 0.035296 0.062 Uiso 1 1 calc R U . . .
H4A6 H 0.400368 0.812659 0.079036 0.062 Uiso 1 1 calc R U . . .
H5A6 H 0.322658 0.798252 0.094181 0.062 Uiso 1 1 calc R U . . .
O2A6 O 0.35834(6) 0.63076(10) 0.06929(5) 0.0350(3) Uani 1 1 d . . . . .
C1A6 C 0.29418(9) 0.56443(15) 0.06622(6) 0.0337(3) Uani 1 1 d . . . . .
O1A6 O 0.23423(8) 0.61564(13) 0.06447(7) 0.0622(4) Uani 1 1 d . . . . .
C2A6 C 0.30435(8) 0.41870(14) 0.06473(5) 0.0281(3) Uani 1 1 d . . . . .
C3A6 C 0.37248(8) 0.36153(14) 0.06142(5) 0.0271(3) Uani 1 1 d . . . . .
H3A6 H 0.414090 0.414200 0.060665 0.033 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
C4A1 O2A1 1.453(5) . ?
O2A1 C1A1 1.350(6) . ?
O1A1 C1A1 1.182(5) . ?
C1A1 O1A7 1.22(3) . ?
C1A1 O2A7 1.32(3) . ?
C1A1 C2A1 1.497(2) . ?
C4A7 O2A7 1.411(18) . ?
C2A1 C3A3 1.391(2) . ?
C2A1 C3A1 1.393(2) . ?
C3A1 C2A2 1.386(2) . ?
C4A2 O2A2 1.450(2) . ?
O2A2 C1A2 1.332(2) . ?
C1A2 O1A2 1.203(2) . ?
C1A2 C2A2 1.495(2) . ?
C2A2 C3A2 1.395(2) . ?
C3A2 C2A3 1.389(2) . ?
C4A3 O2A3 1.451(2) . ?
O2A3 C1A3 1.333(2) . ?
C1A3 O1A3 1.210(2) . ?
C1A3 C2A3 1.495(2) . ?
C2A3 C3A3 1.394(2) . ?
C4A4 O2A4 1.4522(18) . ?
O2A4 C1A4 1.3337(18) . ?
C1A4 O1A4 1.2034(19) . ?
C1A4 C2A4 1.496(2) . ?
C2A4 C3A4 1.389(2) . ?
C2A4 C3A6 1.394(2) . ?
C3A4 C2A5 1.391(2) . ?
C4A5 O2A5 1.446(2) . ?
O2A5 C1A5 1.335(2) . ?
C1A5 O1A5 1.207(2) . ?
C1A5 C2A5 1.495(2) . ?
C2A5 C3A5 1.389(2) . ?
C3A5 C2A6 1.392(2) . ?
C4A6 O2A6 1.4526(18) . ?
O2A6 C1A6 1.3303(19) . ?
C1A6 O1A6 1.197(2) . ?
C1A6 C2A6 1.493(2) . ?
C2A6 C3A6 1.389(2) . ?

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
C1A1 O2A1 C4A1 112.0(4) . . ?
O1A7 C1A1 O2A7 126.7(15) . . ?
O1A1 C1A1 O2A1 123.6(3) . . ?
O1A1 C1A1 C2A1 123.2(3) . . ?
O1A7 C1A1 C2A1 112.6(15) . . ?
O2A7 C1A1 C2A1 120.8(9) . . ?
O2A1 C1A1 C2A1 113.1(3) . . ?
C1A1 O2A7 C4A7 100.1(16) . . ?
C3A3 C2A1 C3A1 119.81(15) . . ?
C3A3 C2A1 C1A1 122.58(16) . . ?
C3A1 C2A1 C1A1 117.61(15) . . ?
C2A2 C3A1 C2A1 120.33(14) . . ?
C1A2 O2A2 C4A2 115.60(14) . . ?
O1A2 C1A2 O2A2 124.27(16) . . ?
O1A2 C1A2 C2A2 123.33(15) . . ?
O2A2 C1A2 C2A2 112.39(14) . . ?
C3A1 C2A2 C3A2 119.91(15) . . ?
C3A1 C2A2 C1A2 122.43(14) . . ?
C3A2 C2A2 C1A2 117.64(14) . . ?
C2A3 C3A2 C2A2 119.88(15) . . ?
C1A3 O2A3 C4A3 115.78(14) . . ?
O1A3 C1A3 O2A3 125.03(15) . . ?
O1A3 C1A3 C2A3 123.00(16) . . ?
O2A3 C1A3 C2A3 111.97(14) . . ?
C3A2 C2A3 C3A3 120.18(14) . . ?
C3A2 C2A3 C1A3 121.74(15) . . ?
C3A3 C2A3 C1A3 118.08(14) . . ?
C2A1 C3A3 C2A3 119.88(15) . . ?
C1A4 O2A4 C4A4 115.46(12) . . ?
O1A4 C1A4 O2A4 124.30(14) . . ?
O1A4 C1A4 C2A4 123.94(14) . . ?
O2A4 C1A4 C2A4 111.75(12) . . ?
C3A4 C2A4 C3A6 119.86(13) . . ?
C3A4 C2A4 C1A4 118.36(13) . . ?
C3A6 C2A4 C1A4 121.77(13) . . ?
C2A4 C3A4 C2A5 120.54(13) . . ?
C1A5 O2A5 C4A5 116.43(15) . . ?
O1A5 C1A5 O2A5 124.52(15) . . ?
O1A5 C1A5 C2A5 123.52(15) . . ?
O2A5 C1A5 C2A5 111.96(14) . . ?
C3A5 C2A5 C3A4 119.49(13) . . ?
C3A5 C2A5 C1A5 122.16(14) . . ?
C3A4 C2A5 C1A5 118.34(14) . . ?
C2A5 C3A5 C2A6 120.19(14) . . ?
C1A6 O2A6 C4A6 114.95(12) . . ?
O1A6 C1A6 O2A6 123.82(15) . . ?
O1A6 C1A6 C2A6 123.15(15) . . ?
O2A6 C1A6 C2A6 113.03(13) . . ?
C3A6 C2A6 C3A5 120.22(14) . . ?
C3A6 C2A6 C1A6 122.26(13) . . ?
C3A5 C2A6 C1A6 117.51(13) . . ?
C2A6 C3A6 C2A4 119.68(13) . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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 2165097'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2022-04-07 deposited with the CCDC.	2022-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H10 O5'
_chemical_formula_sum            'C8 H10 O5'
_chemical_formula_weight         186.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   3.8849(7)
_cell_length_b                   30.166(4)
_cell_length_c                   7.806(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.79(3)
_cell_angle_gamma                90
_cell_volume                     898.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    402
_cell_measurement_theta_min      6.4720
_cell_measurement_theta_max      56.0630

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.000
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.05869
_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.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            2359
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.930
_diffrn_reflns_theta_max         62.428
_diffrn_reflns_theta_full        62.428
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             1384
_reflns_number_gt                680
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1467P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1384
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1563
_refine_ls_R_factor_gt           0.0959
_refine_ls_wR_factor_ref         0.2928
_refine_ls_wR_factor_gt          0.2331
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_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
C4A1 C 0.676(2) 0.2466(2) 0.3853(10) 0.095(2) Uani 1 1 d . . . . .
H6A1 H 0.919541 0.252062 0.386692 0.143 Uiso 1 1 calc R U . . .
H4A1 H 0.597371 0.264887 0.470995 0.143 Uiso 1 1 calc R U . . .
H5A1 H 0.542569 0.253341 0.271907 0.143 Uiso 1 1 calc R U . . .
O2A1 O 0.6274(11) 0.20111(14) 0.4245(6) 0.0858(14) Uani 1 1 d . . . . .
C1A1 C 0.7012(15) 0.1713(2) 0.3098(8) 0.0729(17) Uani 1 1 d . . . . .
O1A1 O 0.8116(12) 0.18157(14) 0.1797(5) 0.0907(15) Uani 1 1 d . . . . .
C2A1 C 0.6395(14) 0.12653(18) 0.3622(7) 0.0695(17) Uani 1 1 d . . . . .
H2A1 H 0.540081 0.122227 0.460462 0.083 Uiso 1 1 calc R U . . .
C3A1 C 0.7180(14) 0.09174(19) 0.2767(7) 0.0681(17) Uani 1 1 d . . . . .
H3A1 H 0.820958 0.095578 0.179326 0.082 Uiso 1 1 calc R U . . .
O1 O 0.6514(11) 0.05031(12) 0.3282(5) 0.0785(14) Uani 1 1 d . . . . .
C3A2 C 0.7381(14) 0.0151(2) 0.2396(7) 0.0676(16) Uani 1 1 d . . . . .
H3A2 H 0.834465 0.019680 0.140601 0.081 Uiso 1 1 calc R U . . .
C2A2 C 0.6901(15) -0.02551(19) 0.2895(7) 0.0725(18) Uani 1 1 d . . . . .
H2A2 H 0.599013 -0.029979 0.390199 0.087 Uiso 1 1 calc R U . . .
C1A2 C 0.7746(14) -0.06373(18) 0.1925(7) 0.0677(16) Uani 1 1 d . . . . .
O1A2 O 0.8854(12) -0.06233(14) 0.0565(5) 0.0878(15) Uani 1 1 d . . . . .
O2A2 O 0.7240(10) -0.10168(13) 0.2706(5) 0.0785(13) Uani 1 1 d . . . . .
C4A2 C 0.8060(17) -0.14212(19) 0.1893(8) 0.0852(19) Uani 1 1 d . . . . .
H6A2 H 0.641342 -0.146509 0.082547 0.128 Uiso 1 1 calc R U . . .
H4A2 H 0.792697 -0.166586 0.266479 0.128 Uiso 1 1 calc R U . . .
H5A2 H 1.038572 -0.140271 0.164720 0.128 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
C4A1 O2A1 1.425(7) . ?
O2A1 C1A1 1.338(7) . ?
C1A1 O1A1 1.215(6) . ?
C1A1 C2A1 1.443(8) . ?
C2A1 C3A1 1.310(7) . ?
C3A1 O1 1.353(7) . ?
O1 C3A2 1.344(6) . ?
C3A2 C2A2 1.309(7) . ?
C2A2 C1A2 1.451(7) . ?
C1A2 O1A2 1.218(6) . ?
C1A2 O2A2 1.329(6) . ?
O2A2 C4A2 1.438(6) . ?

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
C1A1 O2A1 C4A1 116.8(5) . . ?
O1A1 C1A1 O2A1 122.7(6) . . ?
O1A1 C1A1 C2A1 125.4(5) . . ?
O2A1 C1A1 C2A1 111.8(5) . . ?
C3A1 C2A1 C1A1 122.5(5) . . ?
C2A1 C3A1 O1 120.9(5) . . ?
C3A2 O1 C3A1 119.8(4) . . ?
C2A2 C3A2 O1 121.5(5) . . ?
C3A2 C2A2 C1A2 122.0(5) . . ?
O1A2 C1A2 O2A2 122.4(5) . . ?
O1A2 C1A2 C2A2 125.4(5) . . ?
O2A2 C1A2 C2A2 112.2(4) . . ?
C1A2 O2A2 C4A2 117.7(4) . . ?

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 2165100'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2022-04-07 deposited with the CCDC.	2022-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H24 N2 O5'
_chemical_formula_sum            'C17 H24 N2 O5'
_chemical_formula_weight         336.38

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      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                   10.0606(2)
_cell_length_b                   11.7335(2)
_cell_length_c                   15.8113(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1866.46(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2758
_cell_measurement_theta_min      4.6860
_cell_measurement_theta_max      75.0360

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.731
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77405
_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.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            6142
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.693
_diffrn_reflns_theta_max         75.788
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.946
_reflns_number_total             3570
_reflns_number_gt                3257
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.621
_reflns_Friedel_fraction_max     0.818
_reflns_Friedel_fraction_full    0.875

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0692P)²+0.0182P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1139 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.16(15)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3570
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1161
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
N1C N 0.0459(2) 0.30824(15) -0.10489(12) 0.0574(4) Uani 1 1 d . . . . .
H1NC H 0.126(4) 0.322(3) -0.112(2) 0.084(10) Uiso 1 1 d . . . . .
C1C C 0.0026(2) 0.19088(17) -0.11745(13) 0.0558(5) Uani 1 1 d . . . . .
H1C H -0.094603 0.189403 -0.121070 0.067 Uiso 1 1 calc R U . . .
C2C C 0.0600(4) 0.1448(2) -0.19959(16) 0.0763(7) Uani 1 1 d . . . . .
H1C2 H 0.156028 0.151761 -0.198291 0.092 Uiso 1 1 calc R U . . .
H2C2 H 0.027288 0.190102 -0.246521 0.092 Uiso 1 1 calc R U . . .
C3C C 0.0225(4) 0.0206(3) -0.21351(18) 0.0887(9) Uani 1 1 d . . . . .
H1C3 H -0.072413 0.015143 -0.223424 0.106 Uiso 1 1 calc R U . . .
H2C3 H 0.067773 -0.007782 -0.263431 0.106 Uiso 1 1 calc R U . . .
C4C C 0.0592(4) -0.0525(2) -0.1384(2) 0.0891(9) Uani 1 1 d . . . . .
H1C4 H 0.155212 -0.056000 -0.133393 0.107 Uiso 1 1 calc R U . . .
H2C4 H 0.026624 -0.129380 -0.147290 0.107 Uiso 1 1 calc R U . . .
C5C C 0.0007(3) -0.00511(19) -0.05699(17) 0.0741(7) Uani 1 1 d . . . . .
H2C5 H 0.028314 -0.052121 -0.009694 0.089 Uiso 1 1 calc R U . . .
H1C5 H -0.095571 -0.007298 -0.060112 0.089 Uiso 1 1 calc R U . . .
C6C C 0.0464(2) 0.11731(18) -0.04257(13) 0.0553(4) Uani 1 1 d . . . . .
H6C H 0.143718 0.118232 -0.039555 0.066 Uiso 1 1 calc R U . . .
N2C N -0.0063(2) 0.16082(18) 0.03657(12) 0.0610(4) Uani 1 1 d . . . . .
H2NC H -0.088(3) 0.139(3) 0.0517(18) 0.063(7) Uiso 1 1 d . . . . .
C1B C 0.0663(2) 0.2276(2) 0.08754(13) 0.0588(5) Uani 1 1 d . . . . .
O1B O 0.17976(17) 0.25635(19) 0.07395(11) 0.0713(4) Uani 1 1 d . . . . .
O2B O -0.00659(19) 0.2586(2) 0.15561(11) 0.0767(5) Uani 1 1 d . . . . .
C2B C 0.0533(3) 0.3258(3) 0.22364(16) 0.0815(8) Uani 1 1 d . . . . .
C3B C -0.0604(5) 0.3378(6) 0.2856(2) 0.1294(19) Uani 1 1 d . . . . .
H2B3 H -0.128600 0.384661 0.261264 0.194 Uiso 1 1 calc R U . . .
H1B3 H -0.028663 0.372443 0.336793 0.194 Uiso 1 1 calc R U . . .
H3B3 H -0.096150 0.263830 0.298192 0.194 Uiso 1 1 calc R U . . .
C4B C 0.1655(4) 0.2602(5) 0.2627(2) 0.1129(13) Uani 1 1 d . . . . .
H2B4 H 0.133416 0.187609 0.281914 0.169 Uiso 1 1 calc R U . . .
H1B4 H 0.200714 0.302137 0.309726 0.169 Uiso 1 1 calc R U . . .
H3B4 H 0.234138 0.248729 0.221367 0.169 Uiso 1 1 calc R U . . .
C5B C 0.0974(5) 0.4409(4) 0.1910(3) 0.1107(13) Uani 1 1 d . . . . .
H2B5 H 0.172053 0.431263 0.153877 0.166 Uiso 1 1 calc R U . . .
H1B5 H 0.122635 0.488371 0.237816 0.166 Uiso 1 1 calc R U . . .
H3B5 H 0.025650 0.476066 0.160752 0.166 Uiso 1 1 calc R U . . .
C3A1 C -0.0272(2) 0.38898(17) -0.07401(13) 0.0542(4) Uani 1 1 d . . . . .
H3A1 H -0.117113 0.374737 -0.065454 0.065 Uiso 1 1 calc R U . . .
C2A1 C 0.0228(2) 0.49714(16) -0.05279(13) 0.0535(4) Uani 1 1 d . . . . .
C1A1 C -0.0707(3) 0.5788(2) -0.0212(2) 0.0733(7) Uani 1 1 d . . . . .
O2A1 O -0.0200(2) 0.68357(15) 0.00586(17) 0.0878(6) Uani 1 1 d . . . . .
O1A1 O -0.1897(2) 0.5675(2) -0.0143(2) 0.1108(10) Uani 1 1 d . . . . .
C3A2 C 0.1121(3) 0.7056(2) 0.00018(19) 0.0740(7) Uani 1 1 d . . . . .
H3A2 H 0.141996 0.775862 0.019617 0.089 Uiso 1 1 calc R U . . .
C2A2 C 0.2011(3) 0.6344(2) -0.03096(16) 0.0650(5) Uani 1 1 d . . . . .
H2A2 H 0.289999 0.655843 -0.033470 0.078 Uiso 1 1 calc R U . . .
C1A2 C 0.1609(2) 0.52318(17) -0.06122(14) 0.0564(5) Uani 1 1 d . . . . .
O1A2 O 0.24294(18) 0.45590(15) -0.09254(13) 0.0714(5) 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
N1C C3A1 1.295(3) . ?
N1C C1C 1.458(3) . ?
C1C C2C 1.520(3) . ?
C1C C6C 1.530(3) . ?
C2C C3C 1.522(4) . ?
C3C C4C 1.510(5) . ?
C4C C5C 1.521(4) . ?
C5C C6C 1.525(3) . ?
C6C N2C 1.452(3) . ?
N2C C1B 1.340(3) . ?
C1B O1B 1.210(3) . ?
C1B O2B 1.352(3) . ?
O2B C2B 1.464(3) . ?
C2B C4B 1.499(6) . ?
C2B C5B 1.511(6) . ?
C2B C3B 1.513(5) . ?
C3A1 C2A1 1.406(3) . ?
C2A1 C1A2 1.429(3) . ?
C2A1 C1A1 1.433(3) . ?
C1A1 O1A1 1.210(4) . ?
C1A1 O2A1 1.398(3) . ?
O2A1 C3A2 1.356(4) . ?
C3A2 C2A2 1.320(4) . ?
C2A2 C1A2 1.448(3) . ?
C1A2 O1A2 1.245(3) . ?

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
C3A1 N1C C1C 125.0(2) . . ?
N1C C1C C2C 109.8(2) . . ?
N1C C1C C6C 109.97(17) . . ?
C2C C1C C6C 110.56(19) . . ?
C1C C2C C3C 111.7(3) . . ?
C4C C3C C2C 111.7(2) . . ?
C3C C4C C5C 111.3(2) . . ?
C4C C5C C6C 110.7(2) . . ?
N2C C6C C5C 110.5(2) . . ?
N2C C6C C1C 111.30(17) . . ?
C5C C6C C1C 109.19(18) . . ?
C1B N2C C6C 121.7(2) . . ?
O1B C1B N2C 124.8(2) . . ?
O1B C1B O2B 125.3(2) . . ?
N2C C1B O2B 109.9(2) . . ?
C1B O2B C2B 120.4(2) . . ?
O2B C2B C4B 109.6(3) . . ?
O2B C2B C5B 110.6(3) . . ?
C4B C2B C5B 112.2(3) . . ?
O2B C2B C3B 102.4(3) . . ?
C4B C2B C3B 110.5(3) . . ?
C5B C2B C3B 111.1(4) . . ?
N1C C3A1 C2A1 123.2(2) . . ?
C3A1 C2A1 C1A2 121.25(19) . . ?
C3A1 C2A1 C1A1 116.9(2) . . ?
C1A2 C2A1 C1A1 121.9(2) . . ?
O1A1 C1A1 O2A1 115.5(2) . . ?
O1A1 C1A1 C2A1 127.4(3) . . ?
O2A1 C1A1 C2A1 117.1(2) . . ?
C3A2 O2A1 C1A1 120.3(2) . . ?
C2A2 C3A2 O2A1 124.7(2) . . ?
C3A2 C2A2 C1A2 120.3(2) . . ?
O1A2 C1A2 C2A1 123.1(2) . . ?
O1A2 C1A2 C2A2 121.2(2) . . ?
C2A1 C1A2 C2A2 115.7(2) . . ?

_refine_diff_density_max         0.142
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.029

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2165099'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2022-04-07 deposited with the CCDC.	2022-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H27 N5 O4'
_chemical_formula_sum            'C20 H27 N5 O4'
_chemical_formula_weight         401.47

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      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                   7.8627(4)
_cell_length_b                   10.6927(5)
_cell_length_c                   24.4593(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2056.38(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    204(2)
_cell_measurement_reflns_used    3911
_cell_measurement_theta_min      3.5200
_cell_measurement_theta_max      75.5570

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.758
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94149
_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.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      204(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            6469
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.614
_diffrn_reflns_theta_max         75.594
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.936
_reflns_number_total             3885
_reflns_number_gt                3651
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.608
_reflns_Friedel_fraction_max     0.809
_reflns_Friedel_fraction_full    0.857

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0813P)²+0.5035P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1285 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.19(17)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3885
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1415
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
N1C N 0.5036(3) 0.3944(3) 0.09481(11) 0.0291(5) Uani 1 1 d . . . . .
H1NC H 0.573(5) 0.387(4) 0.1188(15) 0.029(9) Uiso 1 1 d . . . . .
C1C C 0.5650(4) 0.4376(3) 0.04175(12) 0.0266(6) Uani 1 1 d . . . . .
H1C H 0.486249 0.408863 0.013352 0.032 Uiso 1 1 calc R U . . .
C2C C 0.5744(5) 0.5806(3) 0.03981(14) 0.0357(7) Uani 1 1 d . . . . .
H2C2 H 0.462052 0.615282 0.045988 0.043 Uiso 1 1 calc R U . . .
H1C2 H 0.648695 0.610252 0.068688 0.043 Uiso 1 1 calc R U . . .
C3C C 0.6411(5) 0.6250(3) -0.01500(15) 0.0405(8) Uani 1 1 d . . . . .
H2C3 H 0.653689 0.715203 -0.014284 0.049 Uiso 1 1 calc R U . . .
H1C3 H 0.559538 0.604155 -0.043321 0.049 Uiso 1 1 calc R U . . .
C4C C 0.8111(5) 0.5656(3) -0.02852(17) 0.0442(9) Uani 1 1 d . . . . .
H1C4 H 0.896341 0.595689 -0.003066 0.053 Uiso 1 1 calc R U . . .
H2C4 H 0.845280 0.590513 -0.065030 0.053 Uiso 1 1 calc R U . . .
C5C C 0.8029(4) 0.4227(3) -0.02554(14) 0.0373(7) Uani 1 1 d . . . . .
H1C5 H 0.725862 0.391551 -0.053372 0.045 Uiso 1 1 calc R U . . .
H2C5 H 0.914775 0.387973 -0.032549 0.045 Uiso 1 1 calc R U . . .
C6C C 0.7415(4) 0.3811(3) 0.03066(12) 0.0272(6) Uani 1 1 d . . . . .
H6C H 0.820783 0.413482 0.058151 0.033 Uiso 1 1 calc R U . . .
N2C N 0.7387(4) 0.2450(2) 0.03478(10) 0.0291(5) Uani 1 1 d . . . . .
H2NC H 0.729(5) 0.202(4) 0.0074(16) 0.035(10) Uiso 1 1 d . . . . .
C1B C 0.7671(4) 0.1884(3) 0.08248(12) 0.0281(6) Uani 1 1 d . . . . .
O1B O 0.7976(3) 0.24329(19) 0.12570(8) 0.0306(5) Uani 1 1 d . . . . .
O2B O 0.7563(3) 0.06297(19) 0.07797(8) 0.0317(5) Uani 1 1 d . . . . .
C2B C 0.7574(5) -0.0150(3) 0.12754(13) 0.0352(7) Uani 1 1 d . . . . .
C3B C 0.7246(5) -0.1459(3) 0.10473(16) 0.0423(8) Uani 1 1 d . . . . .
H2B3 H 0.616483 -0.147290 0.086494 0.063 Uiso 1 1 calc R U . . .
H1B3 H 0.723956 -0.205317 0.134147 0.063 Uiso 1 1 calc R U . . .
H3B3 H 0.812710 -0.167240 0.079221 0.063 Uiso 1 1 calc R U . . .
C4B C 0.9315(5) -0.0084(3) 0.15486(16) 0.0462(9) Uani 1 1 d . . . . .
H2B4 H 1.016614 -0.038950 0.130093 0.069 Uiso 1 1 calc R U . . .
H1B4 H 0.931107 -0.058794 0.187340 0.069 Uiso 1 1 calc R U . . .
H3B4 H 0.956449 0.076790 0.164354 0.069 Uiso 1 1 calc R U . . .
C5B C 0.6158(5) 0.0234(4) 0.16580(16) 0.0476(9) Uani 1 1 d . . . . .
H2B5 H 0.637635 0.106080 0.179429 0.071 Uiso 1 1 calc R U . . .
H1B5 H 0.610131 -0.034190 0.195847 0.071 Uiso 1 1 calc R U . . .
H3B5 H 0.509572 0.022829 0.146434 0.071 Uiso 1 1 calc R U . . .
C1A C 0.3410(4) 0.3683(3) 0.10592(12) 0.0268(6) Uani 1 1 d . . . . .
O1A O 0.2228(3) 0.3851(2) 0.07338(8) 0.0312(5) Uani 1 1 d . . . . .
C2A C 0.3141(4) 0.3135(3) 0.16116(13) 0.0293(6) Uani 1 1 d . . . . .
H2A H 0.407276 0.290757 0.182348 0.035 Uiso 1 1 calc R U . . .
C3A C 0.1586(4) 0.2971(3) 0.18030(12) 0.0279(6) Uani 1 1 d . . . . .
H3A H 0.067468 0.326301 0.159694 0.034 Uiso 1 1 calc R U . . .
N1H N 0.1729(4) 0.1158(2) 0.29773(10) 0.0333(6) Uani 1 1 d . . . . .
O1H O 0.2512(4) 0.0432(2) 0.32980(10) 0.0475(6) Uani 1 1 d . . . . .
N2H N 0.2472(3) 0.1667(2) 0.25445(11) 0.0338(6) Uani 1 1 d . . . . .
N3H N 0.1243(3) 0.2375(2) 0.23037(10) 0.0284(5) Uani 1 1 d . . . . .
C1H C 0.0038(4) 0.1530(3) 0.30243(13) 0.0328(7) Uani 1 1 d . . . . .
C2H C -0.0271(4) 0.2314(3) 0.25837(12) 0.0278(6) Uani 1 1 d . . . . .
C3H C -0.1855(4) 0.2880(3) 0.25047(13) 0.0327(6) Uani 1 1 d . . . . .
H3H H -0.207089 0.342214 0.221570 0.039 Uiso 1 1 calc R U . . .
C4H C -0.3074(4) 0.2573(4) 0.28875(15) 0.0431(8) Uani 1 1 d . . . . .
H4H H -0.415718 0.291145 0.285011 0.052 Uiso 1 1 calc R U . . .
C5H C -0.2755(5) 0.1774(4) 0.33307(16) 0.0470(9) Uani 1 1 d . . . . .
H5H H -0.362836 0.160196 0.357568 0.056 Uiso 1 1 calc R U . . .
C6H C -0.1193(5) 0.1241(3) 0.34124(14) 0.0412(8) Uani 1 1 d . . . . .
H6H H -0.096995 0.071984 0.370822 0.049 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
N1C C1A 1.336(4) . ?
N1C C1C 1.460(4) . ?
C1C C2C 1.531(4) . ?
C1C C6C 1.538(4) . ?
C2C C3C 1.516(5) . ?
C3C C4C 1.516(5) . ?
C4C C5C 1.531(5) . ?
C5C C6C 1.523(4) . ?
C6C N2C 1.460(4) . ?
N2C C1B 1.333(4) . ?
C1B O1B 1.233(4) . ?
C1B O2B 1.348(3) . ?
O2B C2B 1.472(4) . ?
C2B C5B 1.511(5) . ?
C2B C4B 1.525(5) . ?
C2B C3B 1.528(4) . ?
C1A O1A 1.237(4) . ?
C1A C2A 1.488(4) . ?
C2A C3A 1.321(4) . ?
C3A N3H 1.406(4) . ?
N1H O1H 1.264(4) . ?
N1H N2H 1.326(4) . ?
N1H C1H 1.392(4) . ?
N2H N3H 1.361(4) . ?
N3H C2H 1.375(4) . ?
C1H C2H 1.387(4) . ?
C1H C6H 1.391(5) . ?
C2H C3H 1.398(4) . ?
C3H C4H 1.379(5) . ?
C4H C5H 1.403(6) . ?
C5H C6H 1.368(6) . ?

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
C1A N1C C1C 124.3(3) . . ?
N1C C1C C2C 111.1(3) . . ?
N1C C1C C6C 109.3(2) . . ?
C2C C1C C6C 110.1(3) . . ?
C3C C2C C1C 110.9(3) . . ?
C2C C3C C4C 111.5(3) . . ?
C3C C4C C5C 111.8(3) . . ?
C6C C5C C4C 110.3(3) . . ?
N2C C6C C5C 111.0(3) . . ?
N2C C6C C1C 111.5(2) . . ?
C5C C6C C1C 109.3(2) . . ?
C1B N2C C6C 120.7(3) . . ?
O1B C1B N2C 124.5(3) . . ?
O1B C1B O2B 123.8(3) . . ?
N2C C1B O2B 111.7(2) . . ?
C1B O2B C2B 119.7(2) . . ?
O2B C2B C5B 110.6(3) . . ?
O2B C2B C4B 109.9(3) . . ?
C5B C2B C4B 112.2(3) . . ?
O2B C2B C3B 102.5(2) . . ?
C5B C2B C3B 110.5(3) . . ?
C4B C2B C3B 110.7(3) . . ?
O1A C1A N1C 123.9(3) . . ?
O1A C1A C2A 122.3(3) . . ?
N1C C1A C2A 113.7(3) . . ?
C3A C2A C1A 120.4(3) . . ?
C2A C3A N3H 123.1(3) . . ?
O1H N1H N2H 122.2(3) . . ?
O1H N1H C1H 126.1(3) . . ?
N2H N1H C1H 111.7(3) . . ?
N1H N2H N3H 105.1(2) . . ?
N2H N3H C2H 111.9(2) . . ?
N2H N3H C3A 119.5(2) . . ?
C2H N3H C3A 128.4(3) . . ?
C2H C1H C6H 122.8(3) . . ?
C2H C1H N1H 106.0(3) . . ?
C6H C1H N1H 131.1(3) . . ?
N3H C2H C1H 105.3(3) . . ?
N3H C2H C3H 133.0(3) . . ?
C1H C2H C3H 121.7(3) . . ?
C4H C3H C2H 115.0(3) . . ?
C3H C4H C5H 123.0(4) . . ?
C6H C5H C4H 121.8(3) . . ?
C5H C6H C1H 115.6(3) . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 2165101'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2022-04-07 deposited with the CCDC.	2022-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 N2 O3'
_chemical_formula_sum            'C14 H22 N2 O3'
_chemical_formula_weight         266.34

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      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'

_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'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   16.216(3)
_cell_length_b                   16.216(3)
_cell_length_c                   5.1307(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1168.5(5)
_cell_formula_units_Z            3
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1138
_cell_measurement_theta_min      3.1230
_cell_measurement_theta_max      69.5050

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.650
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.08977
_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.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            3687
_diffrn_reflns_av_unetI/netI     0.1297
_diffrn_reflns_av_R_equivalents  0.2058
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.147
_diffrn_reflns_theta_max         70.947
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.678
_diffrn_reflns_point_group_measured_fraction_full 0.708
_reflns_number_total             2043
_reflns_number_gt                1206
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.466
_reflns_Friedel_fraction_max     0.431
_reflns_Friedel_fraction_full    0.456

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 140 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.0(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2043
_refine_ls_number_parameters     218
_refine_ls_number_restraints     157
_refine_ls_R_factor_all          0.1659
_refine_ls_R_factor_gt           0.1419
_refine_ls_wR_factor_ref         0.4401
_refine_ls_wR_factor_gt          0.3939
_refine_ls_goodness_of_fit_ref   1.393
_refine_ls_restrained_S_all      1.342
_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
N1C N 0.1678(7) -0.1121(7) 1.2596(15) 0.070(2) Uani 1 1 d . . . . .
H1NC H 0.148082 -0.111189 1.104627 0.084 Uiso 1 1 calc R U . . .
C1C C 0.2609(9) -0.1078(8) 1.2898(17) 0.064(3) Uani 1 1 d . . . . .
H1C H 0.287173 -0.080306 1.460798 0.077 Uiso 1 1 calc R U . . .
C2C C 0.2437(16) -0.2102(10) 1.282(3) 0.100(5) Uani 1 1 d . . . . .
H2C2 H 0.200221 -0.247555 1.420676 0.120 Uiso 1 1 calc R U . . .
H1C2 H 0.215095 -0.239735 1.117057 0.120 Uiso 1 1 calc R U . . .
C3C C 0.3368(15) -0.2081(13) 1.316(3) 0.105(5) Uani 1 1 d . . . . .
H2C3 H 0.326359 -0.272365 1.303776 0.126 Uiso 1 1 calc R U . . .
H1C3 H 0.362687 -0.183314 1.487102 0.126 Uiso 1 1 calc R U . . .
C4C C 0.4071(16) -0.1464(16) 1.109(3) 0.110(6) Uani 1 1 d . . . . .
H1C4 H 0.382831 -0.173903 0.938598 0.132 Uiso 1 1 calc R U . . .
H2C4 H 0.466915 -0.145231 1.135364 0.132 Uiso 1 1 calc R U . . .
C5C C 0.4250(10) -0.0439(13) 1.115(3) 0.088(4) Uani 1 1 d . . . . .
H2C5 H 0.467907 -0.007254 0.974662 0.105 Uiso 1 1 calc R U . . .
H1C5 H 0.454711 -0.013947 1.278804 0.105 Uiso 1 1 calc R U . . .
C6C C 0.3292(8) -0.0450(7) 1.0839(16) 0.058(2) Uani 1 1 d . . . . .
H6C H 0.302348 -0.070952 0.912069 0.070 Uiso 1 1 calc R U . . .
N2C N 0.3451(8) 0.0514(6) 1.1024(16) 0.071(3) Uani 1 1 d . . . . .
H2NC H 0.336869 0.071234 1.250212 0.086 Uiso 1 1 calc R U . . .
C1B C 0.3725(12) 0.1111(9) 0.895(2) 0.081(4) Uani 1 1 d . . . . .
O1B O 0.3749(8) 0.0844(7) 0.6743(16) 0.091(3) Uani 1 1 d . . . . .
O2BA O 0.374(3) 0.1930(19) 0.970(5) 0.078(7) Uani 0.52(5) 1 d D U P A 1
C2BA C 0.405(3) 0.270(2) 0.775(5) 0.080(8) Uani 0.52(5) 1 d D U P A 1
C3BA C 0.414(4) 0.352(2) 0.938(6) 0.108(12) Uani 0.52(5) 1 d D U P A 1
H2B3 H 0.353175 0.333912 1.013986 0.163 Uiso 0.52(5) 1 calc R U P A 1
H3B3 H 0.459945 0.366172 1.073060 0.163 Uiso 0.52(5) 1 calc R U P A 1
H1B3 H 0.433740 0.406592 0.828935 0.163 Uiso 0.52(5) 1 calc R U P A 1
C4BA C 0.496(3) 0.293(3) 0.653(8) 0.091(8) Uani 0.52(5) 1 d D U P A 1
H1B4 H 0.513403 0.343012 0.527963 0.136 Uiso 0.52(5) 1 calc R U P A 1
H2B4 H 0.544494 0.313289 0.784177 0.136 Uiso 0.52(5) 1 calc R U P A 1
H3B4 H 0.489525 0.237433 0.566585 0.136 Uiso 0.52(5) 1 calc R U P A 1
C5BA C 0.325(3) 0.238(3) 0.575(6) 0.083(8) Uani 0.52(5) 1 d D U P A 1
H3B5 H 0.267329 0.223953 0.662801 0.124 Uiso 0.52(5) 1 calc R U P A 1
H1B5 H 0.341409 0.288459 0.451362 0.124 Uiso 0.52(5) 1 calc R U P A 1
H2B5 H 0.316821 0.182508 0.486054 0.124 Uiso 0.52(5) 1 calc R U P A 1
O2BB O 0.416(3) 0.202(2) 0.967(6) 0.085(9) Uani 0.48(5) 1 d D U P A 2
C2BB C 0.452(4) 0.283(2) 0.786(6) 0.088(9) Uani 0.48(5) 1 d D U P A 2
C3BB C 0.490(4) 0.368(2) 0.968(7) 0.116(14) Uani 0.48(5) 1 d D U P A 2
H5B3 H 0.439499 0.363748 1.074894 0.174 Uiso 0.48(5) 1 calc R U P A 2
H6B3 H 0.538917 0.369497 1.076368 0.174 Uiso 0.48(5) 1 calc R U P A 2
H4B3 H 0.516514 0.425889 0.866709 0.174 Uiso 0.48(5) 1 calc R U P A 2
C4BB C 0.528(3) 0.288(3) 0.619(10) 0.117(14) Uani 0.48(5) 1 d D U P A 2
H4B4 H 0.549385 0.341587 0.503122 0.176 Uiso 0.48(5) 1 calc R U P A 2
H5B4 H 0.579715 0.296155 0.726245 0.176 Uiso 0.48(5) 1 calc R U P A 2
H6B4 H 0.503811 0.230709 0.519749 0.176 Uiso 0.48(5) 1 calc R U P A 2
C5BB C 0.367(4) 0.274(3) 0.630(9) 0.111(12) Uani 0.48(5) 1 d D U P A 2
H6B5 H 0.319458 0.270353 0.747021 0.167 Uiso 0.48(5) 1 calc R U P A 2
H4B5 H 0.388088 0.327867 0.517472 0.167 Uiso 0.48(5) 1 calc R U P A 2
H5B5 H 0.340560 0.216673 0.526092 0.167 Uiso 0.48(5) 1 calc R U P A 2
C1A C 0.1137(9) -0.1174(12) 1.459(2) 0.084(4) Uani 1 1 d . . . . .
O1A O 0.1377(7) -0.1168(9) 1.6894(17) 0.103(4) Uani 1 1 d . . . . .
C2A C 0.0242(11) -0.1220(13) 1.387(2) 0.088(4) Uani 1 1 d . . . . .
C3A C -0.0463(16) -0.127(2) 1.311(4) 0.123(6) Uani 1 1 d . . . . .
H3A H -0.102165 -0.130450 1.251010 0.148 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
N1C C1A 1.321(16) . ?
N1C C1C 1.483(16) . ?
C1C C6C 1.501(15) . ?
C1C C2C 1.541(17) . ?
C2C C3C 1.50(3) . ?
C3C C4C 1.51(3) . ?
C4C C5C 1.54(3) . ?
C5C C6C 1.554(17) . ?
C6C N2C 1.454(14) . ?
N2C C1B 1.355(15) . ?
C1B O1B 1.220(15) . ?
C1B O2BB 1.33(3) . ?
C1B O2BA 1.37(3) . ?
O2BA C2BA 1.48(2) . ?
C2BA C4BA 1.46(5) . ?
C2BA C3BA 1.51(3) . ?
C2BA C5BA 1.53(5) . ?
O2BB C2BB 1.47(2) . ?
C2BB C4BB 1.47(5) . ?
C2BB C3BB 1.52(3) . ?
C2BB C5BB 1.53(5) . ?
C1A O1A 1.245(18) . ?
C1A C2A 1.46(2) . ?
C2A C3A 1.17(3) . ?

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
C1A N1C C1C 123.3(9) . . ?
N1C C1C C6C 110.3(8) . . ?
N1C C1C C2C 108.3(11) . . ?
C6C C1C C2C 112.9(11) . . ?
C3C C2C C1C 109.5(13) . . ?
C2C C3C C4C 110.5(12) . . ?
C3C C4C C5C 111.9(13) . . ?
C4C C5C C6C 109.8(13) . . ?
N2C C6C C1C 111.0(8) . . ?
N2C C6C C5C 110.0(10) . . ?
C1C C6C C5C 109.3(9) . . ?
C1B N2C C6C 122.4(8) . . ?
O1B C1B O2BB 123.9(17) . . ?
O1B C1B N2C 122.2(11) . . ?
O2BB C1B N2C 112.1(14) . . ?
O1B C1B O2BA 128.1(15) . . ?
N2C C1B O2BA 108.2(13) . . ?
C1B O2BA C2BA 117(2) . . ?
C4BA C2BA O2BA 112(3) . . ?
C4BA C2BA C3BA 112(3) . . ?
O2BA C2BA C3BA 101.9(19) . . ?
C4BA C2BA C5BA 112.1(19) . . ?
O2BA C2BA C5BA 107(2) . . ?
C3BA C2BA C5BA 111(3) . . ?
C1B O2BB C2BB 124(2) . . ?
C4BB C2BB O2BB 111(3) . . ?
C4BB C2BB C3BB 111(3) . . ?
O2BB C2BB C3BB 103(2) . . ?
C4BB C2BB C5BB 113(3) . . ?
O2BB C2BB C5BB 108(3) . . ?
C3BB C2BB C5BB 111(3) . . ?
O1A C1A N1C 122.7(13) . . ?
O1A C1A C2A 122.5(12) . . ?
N1C C1A C2A 114.8(11) . . ?
C3A C2A C1A 175.0(15) . . ?

_refine_diff_density_max         0.374
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.095

