# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_shi_3445_fldu
_database_code_depnum_ccdc_archive 'CCDC 2430401'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry, Iasi
Romania
;
_audit_update_record             
;
2025-03-11 deposited with the CCDC.	2025-06-27 downloaded from the CCDC.
;
_audit_creation_date             2025-03-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7181)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H10 N2 O3'
_chemical_formula_sum            'C10 H10 N2 O3'
_chemical_formula_weight         206.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2'
_chemical_oxdiff_usercomment     RT_13
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 'x, -y-1/2, z-1/2'
8 '-x-1/2, y-1/2, z'

_cell_length_a                   14.5415(14)
_cell_length_b                   7.0417(6)
_cell_length_c                   19.3451(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1980.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1658
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.6430
_cell_measurement_theta_min      2.0990
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense colourless'
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5862
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.11
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0797
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  81.00   1.00    6.00    --   17.94   0.00-120.00  131
  2  ω     47.00  89.00   1.00    6.00    --   17.94-178.00 150.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0440355000
_diffrn_orient_matrix_UB_12      -0.0015887000
_diffrn_orient_matrix_UB_13      -0.0157641000
_diffrn_orient_matrix_UB_21      -0.0182921000
_diffrn_orient_matrix_UB_22      0.0523215000
_diffrn_orient_matrix_UB_23      0.0281859000
_diffrn_orient_matrix_UB_31      0.0102744000
_diffrn_orient_matrix_UB_32      0.0860669000
_diffrn_orient_matrix_UB_33      -0.0173565000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1324
_reflns_number_total             1753
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXH-1997  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1753
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0439P)²+0.2753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1279
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.58976(12) 0.6321(2) 0.43855(9) 0.0583(5) Uani 1 1 d . . .
O2 O 0.53067(13) 0.7808(2) 0.53235(9) 0.0642(6) Uani 1 1 d . . .
O3 O 0.34834(13) 0.9774(2) 0.39652(9) 0.0553(5) Uani 1 1 d . . .
H3 H 0.385(2) 1.050(4) 0.4209(14) 0.077(10) Uiso 1 1 d . . .
N1 N 0.47505(13) 0.6206(2) 0.37206(9) 0.0382(5) Uani 1 1 d . . .
N2 N 0.56147(15) 0.5681(3) 0.37470(11) 0.0540(6) Uani 1 1 d . . .
C1 C 0.42508(16) 0.5686(3) 0.31014(11) 0.0383(6) Uani 1 1 d . . .
C2 C 0.4561(2) 0.6333(3) 0.24764(13) 0.0553(7) Uani 1 1 d . . .
H2 H 0.5081 0.7100 0.2449 0.066 Uiso 1 1 calc R . .
C3 C 0.4087(2) 0.5822(4) 0.18916(14) 0.0666(8) Uani 1 1 d . . .
H3A H 0.4288 0.6246 0.1462 0.080 Uiso 1 1 calc R . .
C4 C 0.3327(2) 0.4704(4) 0.19339(14) 0.0629(8) Uani 1 1 d . . .
H4 H 0.3007 0.4379 0.1535 0.076 Uiso 1 1 calc R . .
C5 C 0.3033(2) 0.4053(4) 0.25659(14) 0.0629(8) Uani 1 1 d . . .
H5 H 0.2515 0.3281 0.2593 0.075 Uiso 1 1 calc R . .
C6 C 0.34986(17) 0.4534(3) 0.31566(13) 0.0484(7) Uani 1 1 d . . .
H6 H 0.3307 0.4087 0.3585 0.058 Uiso 1 1 calc R . .
C7 C 0.44323(16) 0.7129(3) 0.42811(11) 0.0383(6) Uani 1 1 d . . .
C8 C 0.51747(17) 0.7214(3) 0.47379(14) 0.0459(6) Uani 1 1 d . . .
C9 C 0.34997(16) 0.8018(3) 0.43246(12) 0.0450(6) Uani 1 1 d . . .
H9 H 0.3068 0.7164 0.4091 0.054 Uiso 1 1 calc R . .
C10 C 0.3177(2) 0.8236(4) 0.50630(13) 0.0646(8) Uani 1 1 d . . .
H10A H 0.3558 0.9148 0.5296 0.097 Uiso 1 1 calc R . .
H10B H 0.3219 0.7034 0.5295 0.097 Uiso 1 1 calc R . .
H10C H 0.2551 0.8664 0.5067 0.097 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.378(2) . ?
O1 C8 1.402(3) . ?
O2 C8 1.223(3) . ?
O3 H3 0.88(3) . ?
O3 C9 1.419(3) . ?
N1 N2 1.311(3) . ?
N1 C1 1.448(3) . ?
N1 C7 1.346(3) . ?
C1 C2 1.369(3) . ?
C1 C6 1.366(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.359(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.396(3) . ?
C7 C9 1.496(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.511(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
N2 O1 C8 111.02(18) . . ?
C9 O3 H3 103.6(18) . . ?
N2 N1 C1 116.22(18) . . ?
N2 N1 C7 115.73(19) . . ?
C7 N1 C1 128.0(2) . . ?
N1 N2 O1 103.24(18) . . ?
C2 C1 N1 118.7(2) . . ?
C6 C1 N1 119.2(2) . . ?
C6 C1 C2 122.1(2) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3A 119.7 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N1 C7 C8 105.4(2) . . ?
N1 C7 C9 124.0(2) . . ?
C8 C7 C9 130.3(2) . . ?
O2 C8 O1 119.1(2) . . ?
O2 C8 C7 136.2(3) . . ?
C7 C8 O1 104.6(2) . . ?
O3 C9 C7 110.63(19) . . ?
O3 C9 H9 107.4 . . ?
O3 C9 C10 111.69(19) . . ?
C7 C9 H9 107.4 . . ?
C7 C9 C10 112.1(2) . . ?
C10 C9 H9 107.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.88(3) 1.93(3) 2.808(3) 175(3) 5_676

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 179.5(2) . . . . ?
N1 C1 C6 C5 -180.0(2) . . . . ?
N1 C7 C8 O1 0.9(2) . . . . ?
N1 C7 C8 O2 -177.5(3) . . . . ?
N1 C7 C9 O3 -77.7(3) . . . . ?
N1 C7 C9 C10 156.9(2) . . . . ?
N2 O1 C8 O2 177.67(19) . . . . ?
N2 O1 C8 C7 -1.1(2) . . . . ?
N2 N1 C1 C2 -59.4(3) . . . . ?
N2 N1 C1 C6 119.2(2) . . . . ?
N2 N1 C7 C8 -0.5(2) . . . . ?
N2 N1 C7 C9 173.45(19) . . . . ?
C1 N1 N2 O1 -178.76(16) . . . . ?
C1 N1 C7 C8 177.92(19) . . . . ?
C1 N1 C7 C9 -8.1(3) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C1 C6 C5 -1.4(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C6 C1 C2 C3 1.0(4) . . . . ?
C7 N1 N2 O1 -0.1(2) . . . . ?
C7 N1 C1 C2 122.2(2) . . . . ?
C7 N1 C1 C6 -59.2(3) . . . . ?
C8 O1 N2 N1 0.7(2) . . . . ?
C8 C7 C9 O3 94.6(3) . . . . ?
C8 C7 C9 C10 -30.8(3) . . . . ?
C9 C7 C8 O1 -172.5(2) . . . . ?
C9 C7 C8 O2 9.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.093
_oxdiff_exptl_absorpt_empirical_full_min 0.911
####################################################################### 
# 
# 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_shi_6702_fldu_auto
_database_code_depnum_ccdc_archive 'CCDC 2430404'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry, Iasi
Romania
;
_audit_update_record             
;
2025-03-11 deposited with the CCDC.	2025-06-27 downloaded from the CCDC.
;
_audit_creation_date             2025-03-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H7 F N2 O3'
_chemical_formula_sum            'C10 H7 F N2 O3'
_chemical_formula_weight         222.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2O3F1
_chemical_oxdiff_usercomment     'FA_63, CSD: JADCOH'
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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   11.3436(6)
_cell_length_b                   8.3777(4)
_cell_length_c                   20.5336(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1951.37(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1869
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6427
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.017
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_min         1.984
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  18.00   1.00   20.00    --  -15.29 -90.00 -25.00   41
  2  ω    -49.00  32.00   1.00   20.00    --  -15.29  90.00  89.00   81
  3  ω     12.00  37.00   1.00   20.00    --   17.71  77.00-180.00   25
  4  ω     -8.00  37.00   1.00   20.00    --   17.71  77.00-120.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0345481000
_diffrn_orient_matrix_UB_12      0.0647191000
_diffrn_orient_matrix_UB_13      0.0114717000
_diffrn_orient_matrix_UB_21      0.0106540000
_diffrn_orient_matrix_UB_22      0.0417436000
_diffrn_orient_matrix_UB_23      -0.0294623000
_diffrn_orient_matrix_UB_31      -0.0510180000
_diffrn_orient_matrix_UB_32      -0.0350977000
_diffrn_orient_matrix_UB_33      -0.0139457000
_diffrn_oxdiff_digest_hkl        
;
0132da43e87436a998c068de8c363739a9cedd
;
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1314
_reflns_number_total             1722
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1722
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+0.2046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0979
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.14920(14) 0.68843(17) 0.54053(7) 0.0797(5) Uani 1 1 d . . . . .
O1 O 0.53455(12) 0.31246(17) 0.28860(8) 0.0478(4) Uani 1 1 d . . . . .
O2 O 0.49011(13) 0.33559(16) 0.18114(8) 0.0510(4) Uani 1 1 d . . . . .
O3 O 0.21961(13) 0.64437(17) 0.26989(7) 0.0480(4) Uani 1 1 d . . . . .
N1 N 0.39916(13) 0.45015(16) 0.33253(8) 0.0293(4) Uani 1 1 d . . . . .
N2 N 0.48960(14) 0.36061(19) 0.34735(9) 0.0434(5) Uani 1 1 d . . . . .
C1 C 0.33386(16) 0.5123(2) 0.38750(9) 0.0291(4) Uani 1 1 d . . . . .
C2 C 0.21411(17) 0.4848(2) 0.39051(10) 0.0366(5) Uani 1 1 d . . . . .
H2 H 0.175262 0.425346 0.357470 0.044 Uiso 1 1 calc R U . . .
C3 C 0.15209(19) 0.5458(3) 0.44273(11) 0.0472(6) Uani 1 1 d . . . . .
H3 H 0.069191 0.531449 0.445727 0.057 Uiso 1 1 calc R U . . .
C4 C 0.2114(2) 0.6266(3) 0.48975(11) 0.0496(6) Uani 1 1 d . . . . .
C5 C 0.3312(2) 0.6494(2) 0.48861(11) 0.0502(6) Uani 1 1 d . . . . .
H5 H 0.370257 0.702696 0.523284 0.060 Uiso 1 1 calc R U . . .
C6 C 0.39355(19) 0.5925(2) 0.43557(10) 0.0402(5) Uani 1 1 d . . . . .
H6 H 0.476247 0.608716 0.432459 0.048 Uiso 1 1 calc R U . . .
C7 C 0.37812(16) 0.4653(2) 0.26769(9) 0.0286(4) Uani 1 1 d . . . . .
C8 C 0.46522(17) 0.3713(2) 0.23634(11) 0.0369(5) Uani 1 1 d . . . . .
C9 C 0.28463(17) 0.5600(2) 0.23783(10) 0.0320(5) Uani 1 1 d . . . . .
C10 C 0.27294(19) 0.5465(2) 0.16526(10) 0.0440(6) Uani 1 1 d . . . . .
H10A H 0.256838 0.435247 0.153476 0.066 Uiso 1 1 calc R U . . .
H10B H 0.346446 0.581161 0.144557 0.066 Uiso 1 1 calc R U . . .
H10C H 0.207896 0.614243 0.150346 0.066 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
F1 C4 1.362(2) . ?
O1 N2 1.370(2) . ?
O1 C8 1.419(3) . ?
O2 C8 1.206(2) . ?
O3 C9 1.215(2) . ?
N1 N2 1.307(2) . ?
N1 C1 1.447(2) . ?
N1 C7 1.358(2) . ?
C1 C2 1.379(3) . ?
C1 C6 1.373(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.358(3) . ?
C4 C5 1.372(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.418(3) . ?
C7 C9 1.459(3) . ?
C9 C10 1.500(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
N2 O1 C8 110.93(14) . . ?
N2 N1 C1 115.26(16) . . ?
N2 N1 C7 114.82(16) . . ?
C7 N1 C1 129.86(15) . . ?
N1 N2 O1 104.84(16) . . ?
C2 C1 N1 118.64(17) . . ?
C6 C1 N1 118.99(17) . . ?
C6 C1 C2 122.35(19) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(2) . . ?
C4 C3 H3 120.5 . . ?
F1 C4 C5 118.3(2) . . ?
C3 C4 F1 118.5(2) . . ?
C3 C4 C5 123.2(2) . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.1(2) . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 118.9(2) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
N1 C7 C8 105.70(16) . . ?
N1 C7 C9 126.17(17) . . ?
C8 C7 C9 128.12(18) . . ?
O2 C8 O1 119.66(18) . . ?
O2 C8 C7 136.7(2) . . ?
C7 C8 O1 103.64(17) . . ?
O3 C9 C7 121.98(19) . . ?
O3 C9 C10 121.88(18) . . ?
C7 C9 C10 116.14(17) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O2 0.95 2.37 3.191(2) 144.8 6_556 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C4 C5 C6 -177.25(17) . . . . ?
N1 C1 C2 C3 -179.33(16) . . . . ?
N1 C1 C6 C5 -178.90(17) . . . . ?
N1 C7 C8 O1 -2.17(18) . . . . ?
N1 C7 C8 O2 178.1(2) . . . . ?
N1 C7 C9 O3 4.8(3) . . . . ?
N1 C7 C9 C10 -174.91(16) . . . . ?
N2 O1 C8 O2 -177.50(17) . . . . ?
N2 O1 C8 C7 2.7(2) . . . . ?
N2 N1 C1 C2 -125.64(18) . . . . ?
N2 N1 C1 C6 52.6(2) . . . . ?
N2 N1 C7 C8 1.0(2) . . . . ?
N2 N1 C7 C9 -178.87(16) . . . . ?
C1 N1 N2 O1 178.18(13) . . . . ?
C1 N1 C7 C8 -176.02(16) . . . . ?
C1 N1 C7 C9 4.1(3) . . . . ?
C1 C2 C3 C4 -1.6(3) . . . . ?
C2 C1 C6 C5 -0.7(3) . . . . ?
C2 C3 C4 F1 179.01(17) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 2.7(3) . . . . ?
C4 C5 C6 C1 -1.8(3) . . . . ?
C6 C1 C2 C3 2.5(3) . . . . ?
C7 N1 N2 O1 0.7(2) . . . . ?
C7 N1 C1 C2 51.4(2) . . . . ?
C7 N1 C1 C6 -130.4(2) . . . . ?
C8 O1 N2 N1 -2.2(2) . . . . ?
C8 C7 C9 O3 -175.06(18) . . . . ?
C8 C7 C9 C10 5.2(3) . . . . ?
C9 C7 C8 O1 177.70(16) . . . . ?
C9 C7 C8 O2 -2.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.064
_oxdiff_exptl_absorpt_empirical_full_min 0.942
####################################################################### 
# 
# 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_shi_3473_fldu
_database_code_depnum_ccdc_archive 'CCDC 2430402'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry, Iasi
Romania
;
_audit_update_record             
;
2025-03-11 deposited with the CCDC.	2025-06-27 downloaded from the CCDC.
;
_audit_creation_date             2025-03-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H9 F N2 O3'
_chemical_formula_sum            'C10 H9 F N2 O3'
_chemical_formula_weight         224.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H30 N4 O2 F1'
_chemical_oxdiff_usercomment     RT_104
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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   14.8617(14)
_cell_length_b                   6.9928(8)
_cell_length_c                   19.4887(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2025.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1590
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.2420
_cell_measurement_theta_min      2.0780
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5671
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.016
_diffrn_reflns_theta_max         25.016
_diffrn_reflns_theta_min         2.090
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0797
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  19.00   1.00   15.00    --  -15.60 -99.00 120.00   41
  2  ω     -2.00  25.00   1.00   15.00    --   17.79 -57.00 -90.00   27
  3  ω    -34.00  -6.00   1.00   15.00    --  -15.60 -57.00-150.00   28
  4  ω      4.00  76.00   1.00   15.00    --   17.79  57.00-150.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0115130000
_diffrn_orient_matrix_UB_12      0.0213386000
_diffrn_orient_matrix_UB_13      0.0344728000
_diffrn_orient_matrix_UB_21      0.0403914000
_diffrn_orient_matrix_UB_22      0.0437673000
_diffrn_orient_matrix_UB_23      -0.0114016000
_diffrn_orient_matrix_UB_31      -0.0226206000
_diffrn_orient_matrix_UB_32      0.0889893000
_diffrn_orient_matrix_UB_33      -0.0027061000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1401
_reflns_number_total             1795
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0015(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+0.9221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1330
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.71398(14) 0.4015(3) 0.14779(8) 0.0789(7) Uani 1 1 d . . . . .
O1 O 0.41454(12) 0.6422(3) 0.44265(10) 0.0580(6) Uani 1 1 d . . . . .
O2 O 0.47391(14) 0.7888(3) 0.53619(9) 0.0625(7) Uani 1 1 d . . . . .
O3 O 0.65460(14) 0.9747(3) 0.39875(9) 0.0544(6) Uani 1 1 d . . . . .
H3 H 0.618(2) 1.055(5) 0.4218(16) 0.082 Uiso 1 1 d . U . . .
N1 N 0.52667(13) 0.6253(3) 0.37687(10) 0.0366(5) Uani 1 1 d . . . . .
N2 N 0.44141(15) 0.5767(4) 0.37927(12) 0.0539(7) Uani 1 1 d . . . . .
C1 C 0.57573(17) 0.5676(4) 0.31633(12) 0.0361(6) Uani 1 1 d . . . . .
C2 C 0.64157(19) 0.4324(4) 0.32274(13) 0.0466(7) Uani 1 1 d . . . . .
H2 H 0.654595 0.379445 0.365381 0.056 Uiso 1 1 calc R U . . .
C3 C 0.6883(2) 0.3756(4) 0.26549(14) 0.0570(8) Uani 1 1 d . . . . .
H3A H 0.733245 0.283582 0.268749 0.068 Uiso 1 1 calc R U . . .
C4 C 0.6677(2) 0.4561(4) 0.20390(13) 0.0502(8) Uani 1 1 d . . . . .
C5 C 0.6013(2) 0.5891(5) 0.19656(14) 0.0619(9) Uani 1 1 d . . . . .
H5 H 0.587707 0.639556 0.153646 0.074 Uiso 1 1 calc R U . . .
C6 C 0.5549(2) 0.6471(4) 0.25406(14) 0.0560(8) Uani 1 1 d . . . . .
H6 H 0.509995 0.739177 0.250671 0.067 Uiso 1 1 calc R U . . .
C7 C 0.55884(16) 0.7155(4) 0.43240(12) 0.0356(6) Uani 1 1 d . . . . .
C8 C 0.48596(18) 0.7278(4) 0.47784(14) 0.0449(7) Uani 1 1 d . . . . .
C9 C 0.65165(17) 0.8000(4) 0.43621(13) 0.0426(7) Uani 1 1 d . . . . .
H9 H 0.692892 0.710366 0.413752 0.051 Uiso 1 1 calc R U . . .
C10 C 0.6834(2) 0.8253(5) 0.50911(14) 0.0649(9) Uani 1 1 d . . . . .
H10A H 0.744705 0.868384 0.509083 0.097 Uiso 1 1 calc R U . . .
H10B H 0.679334 0.705449 0.532908 0.097 Uiso 1 1 calc R U . . .
H10C H 0.646263 0.918307 0.531760 0.097 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
F1 C4 1.347(3) . ?
O1 N2 1.377(3) . ?
O1 C8 1.398(3) . ?
O2 C8 1.228(3) . ?
O3 H3 0.90(3) . ?
O3 C9 1.424(3) . ?
N1 N2 1.313(3) . ?
N1 C1 1.445(3) . ?
N1 C7 1.341(3) . ?
C1 C2 1.366(3) . ?
C1 C6 1.370(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.360(4) . ?
C4 C5 1.363(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.402(3) . ?
C7 C9 1.502(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.507(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
N2 O1 C8 111.25(19) . . ?
C9 O3 H3 105(2) . . ?
N2 N1 C1 116.3(2) . . ?
N2 N1 C7 115.9(2) . . ?
C7 N1 C1 127.6(2) . . ?
N1 N2 O1 103.0(2) . . ?
C2 C1 N1 118.7(2) . . ?
C2 C1 C6 121.6(2) . . ?
C6 C1 N1 119.7(2) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.2(2) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3A 120.5 . . ?
F1 C4 C3 119.0(3) . . ?
F1 C4 C5 118.5(3) . . ?
C3 C4 C5 122.5(3) . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.6(3) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 119.2(3) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N1 C7 C8 105.3(2) . . ?
N1 C7 C9 123.5(2) . . ?
C8 C7 C9 130.9(2) . . ?
O1 C8 C7 104.5(2) . . ?
O2 C8 O1 119.5(3) . . ?
O2 C8 C7 136.0(3) . . ?
O3 C9 C7 109.9(2) . . ?
O3 C9 H9 107.5 . . ?
O3 C9 C10 111.9(2) . . ?
C7 C9 H9 107.5 . . ?
C7 C9 C10 112.3(2) . . ?
C10 C9 H9 107.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O2 0.90(3) 1.93(4) 2.827(3) 172(3) 5_676 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C4 C5 C6 -179.0(3) . . . . ?
N1 C1 C2 C3 179.6(2) . . . . ?
N1 C1 C6 C5 -179.1(3) . . . . ?
N1 C7 C8 O1 -0.9(3) . . . . ?
N1 C7 C8 O2 177.8(3) . . . . ?
N1 C7 C9 O3 76.2(3) . . . . ?
N1 C7 C9 C10 -158.5(2) . . . . ?
N2 O1 C8 O2 -177.8(2) . . . . ?
N2 O1 C8 C7 1.1(3) . . . . ?
N2 N1 C1 C2 -112.1(3) . . . . ?
N2 N1 C1 C6 67.2(3) . . . . ?
N2 N1 C7 C8 0.4(3) . . . . ?
N2 N1 C7 C9 -173.4(2) . . . . ?
C1 N1 N2 O1 177.46(19) . . . . ?
C1 N1 C7 C8 -176.4(2) . . . . ?
C1 N1 C7 C9 9.8(4) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
C2 C3 C4 F1 179.5(3) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C3 C4 C5 C6 1.6(5) . . . . ?
C4 C5 C6 C1 -1.1(5) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
C7 N1 N2 O1 0.3(3) . . . . ?
C7 N1 C1 C2 64.7(3) . . . . ?
C7 N1 C1 C6 -116.0(3) . . . . ?
C8 O1 N2 N1 -0.8(3) . . . . ?
C8 C7 C9 O3 -95.9(3) . . . . ?
C8 C7 C9 C10 29.4(4) . . . . ?
C9 C7 C8 O1 172.3(2) . . . . ?
C9 C7 C8 O2 -9.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.058
_oxdiff_exptl_absorpt_empirical_full_min 0.915
####################################################################### 
# 
# 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_monocl
_database_code_depnum_ccdc_archive 'CCDC 2432331'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry, Iasi
Romania
;
_audit_update_record             
;
2025-03-19 deposited with the CCDC.	2025-06-27 downloaded from the CCDC.
;
_audit_creation_date             2025-03-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H10 N2 O3'
_chemical_formula_sum            'C10 H10 N2 O3'
_chemical_formula_weight         206.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2O2
_chemical_oxdiff_usercomment     'DC-470 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   41.5257(16)
_cell_length_b                   12.1880(5)
_cell_length_c                   7.6472(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.053(4)
_cell_angle_gamma                90
_cell_volume                     3870.3(3)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3494
_cell_measurement_temperature    288(19)
_cell_measurement_theta_max      69.1560
_cell_measurement_theta_min      4.1940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.144a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1163
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            30898
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         3.193
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      288(19)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  20.00   0.50   40.00    --  -47.51  59.00  96.00  140
  2  ω     39.00  77.00   0.50   50.00    --  106.68 -72.00 102.00   76
  3  ω     39.00 103.00   0.50   50.00    --  106.68 -96.00-141.00  128
  4  ω     91.00 177.00   0.50   50.00    --  106.68  59.00  96.00  172
  5  ω    -25.00  28.00   0.50   40.00    --  -47.51  19.00-120.00  106
  6  ω    -14.00  21.00   0.50   40.00    --  -47.51  19.00 -30.00   70
  7  ω     -7.00  20.00   0.50   40.00    --   47.51 -19.00 -60.00   54
  8  ω    -49.00 -23.00   0.50   50.00    --  -91.75  45.00-180.00   52
  9  ω   -114.00 -85.00   0.50   50.00    --  -91.75 -45.00-150.00   58
 10  ω   -163.00-122.00   0.50   50.00    --  -91.75 -45.00-150.00   82
 11  ω    -49.00 -21.00   0.50   50.00    --  -91.75  45.00 -60.00   56
 12  ω    -51.00 -26.00   0.50   50.00    --  -91.75  45.00  30.00   50
 13  ω     34.00  59.00   0.50   50.00    --  106.68 -59.00 -43.00   50
 14  ω     53.00  81.00   0.50   50.00    --  106.68 -77.00 -90.00   56
 15  ω   -107.00 -35.00   0.50   40.00    --  -47.64 -68.00 -45.00  144
 16  ω    -18.00   8.00   0.50   40.00    --   47.64 -19.00 -90.00   52
 17  ω   -163.00-130.00   0.50   50.00    --  -91.75 -95.00-150.00   66
 18  ω   -116.00 -87.00   0.50   50.00    --  -91.75-125.00-150.00   58
 19  ω    -47.00 -21.00   0.50   50.00    --  -91.75  45.00 -30.00   52
 20  ω   -117.00 -89.00   0.50   50.00    --  -91.75 -95.00-150.00   56
 21  ω    -49.00 -23.00   0.50   50.00    --  -91.75  45.00-120.00   52
 22  ω     35.00  70.00   0.50   50.00    --  106.68 -61.00 -30.00   70
 23  ω     41.00  67.00   0.50   50.00    --  106.68 -61.00-150.00   52
 24  ω     37.00  71.00   0.50   50.00    --  106.68 -61.00   0.00   68
 25  ω     38.00  69.00   0.50   50.00    --  106.68 -61.00  30.00   62
 26  ω    140.00 170.00   0.50   50.00    --  106.68  15.00  90.00   60
 27  ω     93.00 128.00   0.50   50.00    --  106.68  15.00  90.00   70
 28  ω     72.00 104.00   0.50   50.00    --  106.68 -95.00  90.00   64
 29  ω    -85.00 -41.00   0.50   50.00    --  -91.75  69.00  86.00   88
 30  ω    -13.00  23.00   0.50   40.00    --  -47.64  19.00  90.00   72
 31  ω    -14.00  12.00   0.50   40.00    --   47.64 -19.00 -90.00   52
 32  ω    -51.00 -26.00   0.50   50.00    --  -91.75  45.00 120.00   50
 33  ω    -71.00 -46.00   0.50   50.00    --  -91.75  61.00  60.00   50
 34  ω     98.00 124.00   0.50   50.00    --  106.68  45.00 -60.00   52
 35  ω    142.00 168.00   0.50   50.00    --  106.68  45.00 -60.00   52
 36  ω    115.00 158.00   0.50   50.00    --  106.68  61.00   0.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0250808000
_diffrn_orient_matrix_UB_12      -0.0920046000
_diffrn_orient_matrix_UB_13      0.0234426000
_diffrn_orient_matrix_UB_21      -0.0049218000
_diffrn_orient_matrix_UB_22      -0.0347548000
_diffrn_orient_matrix_UB_23      -0.1919640000
_diffrn_orient_matrix_UB_31      0.0268712000
_diffrn_orient_matrix_UB_32      0.0793852000
_diffrn_orient_matrix_UB_33      -0.0567400000
_diffrn_oxdiff_ac3_digest_hkl    41b4b73ebd5d4db7e0e51647ffd288ec7a6caa
_diffrn_oxdiff_digest_hkl        
;
4342d1e7fdf9a6452a3091c45ecf368d1f39c9
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3931
_reflns_number_total             6826
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.137a 64-bit (release 10-09-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         6826
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1703
_refine_ls_R_factor_gt           0.1195
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.152
_refine_ls_shift/su_mean         0.029
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2992
_refine_ls_wR_factor_ref         0.3429
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.504(4)
 0.496(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C6B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C1A(H1AA), C1C(H1CA), C1D(H1DA), C1B(H1BA)
4.b Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C5A(H5A), C7A(H7A), C8A(H8A), C9A(H9A), C4C(H4C), C5C(H5C),
 C7C(H7C), C8C(H8C), C9C(H9C), C4D(H4D), C5D(H5D), C7D(H7D), C8D(H8D), C9D(H9D),
  C4B(H4B), C5B(H5B), C7B(H7B), C8B(H8B), C9B(H9B)
4.c Idealised Me refined as rotating group:
 C2A(H2AA,H2AB,H2AC), C2C(H2CA,H2CB,H2CC), C2D(H2DA,H2DB,H2DC), C2B(H2BA,H2BB,
 H2BC)
4.d Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1C(H1C), O1D(H1D), O1B(H1B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.09076(16) -0.1615(7) 0.9109(17) 0.153(4) Uani 1 1 d . . . . .
H1A H 0.090008 -0.228569 0.918506 0.229 Uiso 1 1 calc R U . . .
O2A O 0.04872(15) 0.5059(5) 0.8366(10) 0.101(2) Uani 1 1 d . . . . .
O3A O 0.09230(17) 0.6068(5) 0.9001(12) 0.112(3) Uani 1 1 d . . . . .
N1A N 0.06620(15) 0.3442(6) 0.8578(10) 0.074(2) Uani 1 1 d . . . . .
N2A N 0.03832(17) 0.3986(7) 0.8364(13) 0.093(3) Uani 1 1 d . . . . .
C1A C 0.0614(2) -0.1222(9) 0.849(2) 0.130(5) Uani 1 1 d . . . . .
H1AA H 0.059257 -0.147464 0.727772 0.156 Uiso 1 1 calc R U . . .
C2A C 0.0341(2) -0.1675(8) 0.9454(19) 0.117(4) Uani 1 1 d . . . . .
H2AA H 0.033456 -0.245586 0.929743 0.176 Uiso 1 1 calc R U . . .
H2AB H 0.014463 -0.135737 0.902520 0.176 Uiso 1 1 calc R U . . .
H2AC H 0.036458 -0.150866 1.067486 0.176 Uiso 1 1 calc R U . . .
C3A C 0.0618(3) 0.0006(7) 0.8436(18) 0.111(5) Uani 1 1 d . . . . .
C4A C 0.0392(2) 0.0605(11) 0.7912(15) 0.095(3) Uani 1 1 d . . . . .
H4A H 0.020613 0.025848 0.751100 0.114 Uiso 1 1 calc R U . . .
C5A C 0.0397(2) 0.1711(8) 0.7884(13) 0.086(3) Uani 1 1 d . . . . .
H5A H 0.022574 0.211757 0.744028 0.104 Uiso 1 1 calc R U . . .
C6A C 0.0654(2) 0.2183(10) 0.8513(15) 0.102(4) Uani 1 1 d . . . . .
C7A C 0.09107(18) 0.1649(7) 0.9287(13) 0.077(3) Uani 1 1 d . . . . .
H7A H 0.107796 0.201801 0.984239 0.093 Uiso 1 1 calc R U . . .
C8A C 0.0899(2) 0.0605(8) 0.9174(14) 0.085(3) Uani 1 1 d . . . . .
H8A H 0.107392 0.020024 0.957297 0.102 Uiso 1 1 calc R U . . .
C9A C 0.09159(19) 0.4080(8) 0.8988(11) 0.075(3) Uani 1 1 d . . . . .
H9A H 0.112245 0.385551 0.929416 0.090 Uiso 1 1 calc R U . . .
C10A C 0.0799(3) 0.5171(9) 0.8850(16) 0.102(4) Uani 1 1 d . . . . .
O1C O 0.34184(13) 0.8341(3) 0.8406(10) 0.091(2) Uani 1 1 d . . . . .
H1C H 0.344141 0.771760 0.879134 0.137 Uiso 1 1 calc R U . . .
O2C O 0.29904(12) 1.5091(3) 0.8964(8) 0.0662(15) Uani 1 1 d . . . . .
O3C O 0.34359(14) 1.6095(4) 0.8466(9) 0.0830(17) Uani 1 1 d . . . . .
N1C N 0.31627(13) 1.3454(4) 0.8782(7) 0.0455(13) Uani 1 1 d . . . . .
N2C N 0.29016(16) 1.4001(5) 0.9124(11) 0.077(2) Uani 1 1 d . . . . .
C1C C 0.31152(19) 0.8754(5) 0.8925(15) 0.078(3) Uani 1 1 d . . . . .
H1CA H 0.308409 0.855224 1.015326 0.094 Uiso 1 1 calc R U . . .
C2C C 0.28468(19) 0.8297(6) 0.7942(13) 0.077(2) Uani 1 1 d . . . . .
H2CA H 0.264902 0.844939 0.854391 0.115 Uiso 1 1 calc R U . . .
H2CB H 0.287397 0.751763 0.783430 0.115 Uiso 1 1 calc R U . . .
H2CC H 0.284023 0.862180 0.679874 0.115 Uiso 1 1 calc R U . . .
C3C C 0.3135(2) 1.0016(5) 0.8842(11) 0.065(2) Uani 1 1 d . . . . .
C4C C 0.28896(15) 1.0642(5) 0.9681(10) 0.0557(18) Uani 1 1 d . . . . .
H4C H 0.272507 1.028597 1.027866 0.067 Uiso 1 1 calc R U . . .
C5C C 0.28947(15) 1.1764(5) 0.9613(11) 0.0571(19) Uani 1 1 d . . . . .
H5C H 0.272256 1.216028 1.006690 0.068 Uiso 1 1 calc R U . . .
C6C C 0.31503(11) 1.2314(5) 0.8883(7) 0.0297(12) Uani 1 1 d . . . . .
C7C C 0.34040(16) 1.1702(4) 0.8166(10) 0.0567(19) Uani 1 1 d . . . . .
H7C H 0.358043 1.205889 0.767938 0.068 Uiso 1 1 calc R U . . .
C8C C 0.33913(15) 1.0552(4) 0.8183(10) 0.0502(17) Uani 1 1 d . . . . .
H8C H 0.356305 1.015288 0.773293 0.060 Uiso 1 1 calc R U . . .
C9C C 0.34120(18) 1.4131(6) 0.8513(11) 0.065(2) Uani 1 1 d . . . . .
H9C H 0.362179 1.390925 0.827720 0.078 Uiso 1 1 calc R U . . .
C10C C 0.33143(18) 1.5177(5) 0.8633(11) 0.0589(19) Uani 1 1 d . . . . .
O1D O 0.40831(12) 0.3287(4) 0.6260(11) 0.100(3) Uani 1 1 d . . . . .
H1D H 0.405826 0.273148 0.684934 0.150 Uiso 1 1 calc R U . . .
O2D O 0.45262(13) 1.0022(3) 0.6571(7) 0.0653(15) Uani 1 1 d . . . . .
O3D O 0.40799(13) 1.1036(3) 0.5921(8) 0.0774(18) Uani 1 1 d . . . . .
N1D N 0.43419(12) 0.8418(4) 0.6410(7) 0.0458(14) Uani 1 1 d . . . . .
N2D N 0.46098(13) 0.8928(4) 0.6710(9) 0.0567(16) Uani 1 1 d . . . . .
C1D C 0.43844(18) 0.3735(5) 0.6606(11) 0.065(2) Uani 1 1 d . . . . .
H1DA H 0.443604 0.351913 0.780830 0.079 Uiso 1 1 calc R U . . .
C2D C 0.46492(18) 0.3268(5) 0.5494(11) 0.064(2) Uani 1 1 d . . . . .
H2DA H 0.465547 0.248537 0.563329 0.096 Uiso 1 1 calc R U . . .
H2DB H 0.485180 0.357565 0.584944 0.096 Uiso 1 1 calc R U . . .
H2DC H 0.460967 0.344420 0.428943 0.096 Uiso 1 1 calc R U . . .
C3D C 0.43723(15) 0.4999(5) 0.6619(9) 0.0445(15) Uani 1 1 d . . . . .
C4D C 0.46180(15) 0.5596(5) 0.7145(10) 0.0535(18) Uani 1 1 d . . . . .
H4D H 0.480181 0.523883 0.754395 0.064 Uiso 1 1 calc R U . . .
C5D C 0.46150(17) 0.6719(5) 0.7129(10) 0.0550(18) Uani 1 1 d . . . . .
H5D H 0.478705 0.712501 0.756243 0.066 Uiso 1 1 calc R U . . .
C6D C 0.43420(13) 0.7226(4) 0.6434(9) 0.0391(15) Uani 1 1 d . . . . .
C7D C 0.40912(16) 0.6624(5) 0.5752(9) 0.0509(17) Uani 1 1 d . . . . .
H7D H 0.391674 0.697430 0.523103 0.061 Uiso 1 1 calc R U . . .
C8D C 0.41015(17) 0.5525(5) 0.5847(10) 0.0584(19) Uani 1 1 d . . . . .
H8D H 0.393196 0.510779 0.540995 0.070 Uiso 1 1 calc R U . . .
C9D C 0.40971(16) 0.9055(4) 0.6024(8) 0.0436(15) Uani 1 1 d . . . . .
H9D H 0.388992 0.881878 0.575432 0.052 Uiso 1 1 calc R U . . .
C10D C 0.41993(19) 1.0145(5) 0.6085(9) 0.0538(19) Uani 1 1 d . . . . .
O1B O 0.15880(13) 1.1689(4) 0.6299(12) 0.110(3) Uani 1 1 d . . . . .
H1B H 0.151430 1.205026 0.548655 0.166 Uiso 1 1 calc R U . . .
O2B O 0.20191(14) 0.4941(4) 0.6005(8) 0.0769(17) Uani 1 1 d . . . . .
O3B O 0.15727(13) 0.3938(4) 0.6588(9) 0.0850(19) Uani 1 1 d . . . . .
N1B N 0.18419(14) 0.6575(4) 0.6170(8) 0.0538(15) Uani 1 1 d . . . . .
N2B N 0.21007(15) 0.6029(5) 0.5852(11) 0.076(2) Uani 1 1 d . . . . .
C1B C 0.18935(18) 1.1287(6) 0.5838(11) 0.063(2) Uani 1 1 d . . . . .
H1BA H 0.194084 1.147019 0.461693 0.075 Uiso 1 1 calc R U . . .
C2B C 0.21503(17) 1.1706(5) 0.6982(14) 0.073(2) Uani 1 1 d . . . . .
H2BA H 0.207943 1.237020 0.753599 0.109 Uiso 1 1 calc R U . . .
H2BB H 0.233913 1.185364 0.629791 0.109 Uiso 1 1 calc R U . . .
H2BC H 0.219993 1.116807 0.785841 0.109 Uiso 1 1 calc R U . . .
C3B C 0.18682(19) 1.0079(6) 0.6043(10) 0.0578(19) Uani 1 1 d . . . . .
C4B C 0.21169(17) 0.9396(6) 0.5322(12) 0.069(2) Uani 1 1 d . . . . .
H4B H 0.228922 0.974084 0.477503 0.082 Uiso 1 1 calc R U . . .
C5B C 0.21183(16) 0.8263(5) 0.5384(12) 0.062(2) Uani 1 1 d . . . . .
H5B H 0.229075 0.785563 0.496106 0.074 Uiso 1 1 calc R U . . .
C6B C 0.18484(17) 0.7762(5) 0.6112(11) 0.064(2) Uani 1 1 d . U . . .
C7B C 0.15959(19) 0.8312(5) 0.6756(12) 0.071(2) Uani 1 1 d . . . . .
H7B H 0.141634 0.794747 0.719187 0.085 Uiso 1 1 calc R U . . .
C8B C 0.16145(18) 0.9495(5) 0.6746(11) 0.067(2) Uani 1 1 d . . . . .
H8B H 0.144554 0.988619 0.724335 0.081 Uiso 1 1 calc R U . . .
C9B C 0.15809(18) 0.5904(5) 0.6548(14) 0.076(3) Uani 1 1 d . . . . .
H9B H 0.137141 0.610535 0.683173 0.092 Uiso 1 1 calc R U . . .
C10B C 0.17056(17) 0.4891(6) 0.6403(11) 0.0604(19) 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
O1A H1A 0.8200 . ?
O1A C1A 1.395(13) . ?
O2A N2A 1.377(10) . ?
O2A C10A 1.352(12) . ?
O3A C10A 1.215(11) . ?
N1A N2A 1.344(9) . ?
N1A C6A 1.535(13) . ?
N1A C9A 1.347(10) . ?
C1A H1AA 0.9800 . ?
C1A C2A 1.460(16) . ?
C1A C3A 1.497(12) . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 0.9600 . ?
C3A C4A 1.256(16) . ?
C3A C8A 1.486(15) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.349(15) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.306(12) . ?
C6A C7A 1.380(13) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.276(12) . ?
C8A H8A 0.9300 . ?
C9A H9A 0.9300 . ?
C9A C10A 1.420(13) . ?
O1C H1C 0.8200 . ?
O1C C1C 1.413(10) . ?
O2C N2C 1.384(8) . ?
O2C C10C 1.373(8) . ?
O3C C10C 1.234(8) . ?
N1C N2C 1.300(8) . ?
N1C C6C 1.392(8) . ?
N1C C9C 1.341(9) . ?
C1C H1CA 0.9800 . ?
C1C C2C 1.455(11) . ?
C1C C3C 1.541(9) . ?
C2C H2CA 0.9600 . ?
C2C H2CB 0.9600 . ?
C2C H2CC 0.9600 . ?
C3C C4C 1.425(10) . ?
C3C C8C 1.349(10) . ?
C4C H4C 0.9300 . ?
C4C C5C 1.369(9) . ?
C5C H5C 0.9300 . ?
C5C C6C 1.374(9) . ?
C6C C7C 1.402(8) . ?
C7C H7C 0.9300 . ?
C7C C8C 1.402(7) . ?
C8C H8C 0.9300 . ?
C9C H9C 0.9300 . ?
C9C C10C 1.340(10) . ?
O1D H1D 0.8200 . ?
O1D C1D 1.390(9) . ?
O2D N2D 1.382(6) . ?
O2D C10D 1.415(9) . ?
O3D C10D 1.200(7) . ?
N1D N2D 1.295(7) . ?
N1D C6D 1.453(7) . ?
N1D C9D 1.312(7) . ?
C1D H1DA 0.9800 . ?
C1D C2D 1.503(10) . ?
C1D C3D 1.542(8) . ?
C2D H2DA 0.9600 . ?
C2D H2DB 0.9600 . ?
C2D H2DC 0.9600 . ?
C3D C4D 1.315(9) . ?
C3D C8D 1.422(10) . ?
C4D H4D 0.9300 . ?
C4D C5D 1.368(9) . ?
C5D H5D 0.9300 . ?
C5D C6D 1.396(9) . ?
C6D C7D 1.376(8) . ?
C7D H7D 0.9300 . ?
C7D C8D 1.343(9) . ?
C8D H8D 0.9300 . ?
C9D H9D 0.9300 . ?
C9D C10D 1.396(8) . ?
O1B H1B 0.8200 . ?
O1B C1B 1.406(9) . ?
O2B N2B 1.374(8) . ?
O2B C10B 1.338(8) . ?
O3B C10B 1.294(9) . ?
N1B N2B 1.288(8) . ?
N1B C6B 1.448(8) . ?
N1B C9B 1.389(9) . ?
C1B H1BA 0.9800 . ?
C1B C2B 1.470(11) . ?
C1B C3B 1.484(10) . ?
C2B H2BA 0.9600 . ?
C2B H2BB 0.9600 . ?
C2B H2BC 0.9600 . ?
C3B C4B 1.437(10) . ?
C3B C8B 1.381(11) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.381(10) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.393(10) . ?
C6B C7B 1.339(10) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.443(9) . ?
C8B H8B 0.9300 . ?
C9B H9B 0.9300 . ?
C9B C10B 1.343(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
C1A O1A H1A 109.5 . . ?
C10A O2A N2A 113.3(7) . . ?
N2A N1A C6A 118.2(7) . . ?
N2A N1A C9A 114.7(8) . . ?
C9A N1A C6A 126.9(8) . . ?
N1A N2A O2A 101.4(7) . . ?
O1A C1A H1AA 106.9 . . ?
O1A C1A C2A 112.1(12) . . ?
O1A C1A C3A 110.0(9) . . ?
C2A C1A H1AA 106.9 . . ?
C2A C1A C3A 113.7(10) . . ?
C3A C1A H1AA 106.9 . . ?
C1A C2A H2AA 109.4 . . ?
C1A C2A H2AB 109.5 . . ?
C1A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
C4A C3A C1A 125.4(12) . . ?
C4A C3A C8A 115.0(8) . . ?
C8A C3A C1A 119.4(11) . . ?
C3A C4A H4A 117.5 . . ?
C3A C4A C5A 125.0(9) . . ?
C5A C4A H4A 117.5 . . ?
C4A C5A H5A 121.7 . . ?
C6A C5A C4A 116.6(10) . . ?
C6A C5A H5A 121.7 . . ?
C5A C6A N1A 117.9(10) . . ?
C5A C6A C7A 125.5(11) . . ?
C7A C6A N1A 116.2(8) . . ?
C6A C7A H7A 122.8 . . ?
C8A C7A C6A 114.3(9) . . ?
C8A C7A H7A 122.8 . . ?
C3A C8A H8A 118.5 . . ?
C7A C8A C3A 123.1(8) . . ?
C7A C8A H8A 118.5 . . ?
N1A C9A H9A 127.6 . . ?
N1A C9A C10A 104.8(8) . . ?
C10A C9A H9A 127.6 . . ?
O2A C10A C9A 104.7(9) . . ?
O3A C10A O2A 121.5(9) . . ?
O3A C10A C9A 133.7(11) . . ?
C1C O1C H1C 109.5 . . ?
C10C O2C N2C 110.5(5) . . ?
N2C N1C C6C 118.0(5) . . ?
N2C N1C C9C 111.0(6) . . ?
C9C N1C C6C 130.7(6) . . ?
N1C N2C O2C 104.6(6) . . ?
O1C C1C H1CA 107.3 . . ?
O1C C1C C2C 113.6(8) . . ?
O1C C1C C3C 107.3(6) . . ?
C2C C1C H1CA 107.3 . . ?
C2C C1C C3C 113.7(6) . . ?
C3C C1C H1CA 107.3 . . ?
C1C C2C H2CA 109.5 . . ?
C1C C2C H2CB 109.5 . . ?
C1C C2C H2CC 109.5 . . ?
H2CA C2C H2CB 109.5 . . ?
H2CA C2C H2CC 109.5 . . ?
H2CB C2C H2CC 109.5 . . ?
C4C C3C C1C 118.6(7) . . ?
C8C C3C C1C 122.7(7) . . ?
C8C C3C C4C 118.2(6) . . ?
C3C C4C H4C 119.7 . . ?
C5C C4C C3C 120.5(7) . . ?
C5C C4C H4C 119.8 . . ?
C4C C5C H5C 119.5 . . ?
C4C C5C C6C 121.0(6) . . ?
C6C C5C H5C 119.5 . . ?
N1C C6C C7C 118.7(5) . . ?
C5C C6C N1C 122.5(5) . . ?
C5C C6C C7C 118.7(5) . . ?
C6C C7C H7C 120.0 . . ?
C8C C7C C6C 120.0(5) . . ?
C8C C7C H7C 120.0 . . ?
C3C C8C C7C 121.2(6) . . ?
C3C C8C H8C 119.4 . . ?
C7C C8C H8C 119.4 . . ?
N1C C9C H9C 125.0 . . ?
C10C C9C N1C 110.0(7) . . ?
C10C C9C H9C 125.0 . . ?
O3C C10C O2C 119.3(6) . . ?
O3C C10C C9C 136.9(8) . . ?
C9C C10C O2C 103.7(6) . . ?
C1D O1D H1D 109.4 . . ?
N2D O2D C10D 111.3(4) . . ?
N2D N1D C6D 118.6(5) . . ?
N2D N1D C9D 114.9(5) . . ?
C9D N1D C6D 126.5(5) . . ?
N1D N2D O2D 103.5(5) . . ?
O1D C1D H1DA 105.6 . . ?
O1D C1D C2D 113.7(7) . . ?
O1D C1D C3D 111.4(6) . . ?
C2D C1D H1DA 105.6 . . ?
C2D C1D C3D 114.0(6) . . ?
C3D C1D H1DA 105.6 . . ?
C1D C2D H2DA 109.4 . . ?
C1D C2D H2DB 109.5 . . ?
C1D C2D H2DC 109.5 . . ?
H2DA C2D H2DB 109.5 . . ?
H2DA C2D H2DC 109.5 . . ?
H2DB C2D H2DC 109.5 . . ?
C4D C3D C1D 122.0(6) . . ?
C4D C3D C8D 119.4(6) . . ?
C8D C3D C1D 118.2(6) . . ?
C3D C4D H4D 118.6 . . ?
C3D C4D C5D 122.9(6) . . ?
C5D C4D H4D 118.6 . . ?
C4D C5D H5D 121.5 . . ?
C4D C5D C6D 117.0(6) . . ?
C6D C5D H5D 121.5 . . ?
C5D C6D N1D 116.6(5) . . ?
C7D C6D N1D 121.9(5) . . ?
C7D C6D C5D 121.5(5) . . ?
C6D C7D H7D 120.4 . . ?
C8D C7D C6D 119.2(6) . . ?
C8D C7D H7D 120.4 . . ?
C3D C8D H8D 120.1 . . ?
C7D C8D C3D 119.8(6) . . ?
C7D C8D H8D 120.1 . . ?
N1D C9D H9D 125.7 . . ?
N1D C9D C10D 108.7(6) . . ?
C10D C9D H9D 125.7 . . ?
O3D C10D O2D 121.3(6) . . ?
O3D C10D C9D 137.1(8) . . ?
C9D C10D O2D 101.5(5) . . ?
C1B O1B H1B 109.5 . . ?
C10B O2B N2B 107.7(5) . . ?
N2B N1B C6B 119.7(6) . . ?
N2B N1B C9B 112.7(5) . . ?
C9B N1B C6B 127.6(6) . . ?
N1B N2B O2B 106.1(6) . . ?
O1B C1B H1BA 109.9 . . ?
O1B C1B C2B 112.6(7) . . ?
O1B C1B C3B 104.8(6) . . ?
C2B C1B H1BA 110.0 . . ?
C2B C1B C3B 109.5(6) . . ?
C3B C1B H1BA 110.0 . . ?
C1B C2B H2BA 109.5 . . ?
C1B C2B H2BB 109.5 . . ?
C1B C2B H2BC 109.5 . . ?
H2BA C2B H2BB 109.5 . . ?
H2BA C2B H2BC 109.5 . . ?
H2BB C2B H2BC 109.5 . . ?
C4B C3B C1B 118.9(7) . . ?
C8B C3B C1B 127.4(6) . . ?
C8B C3B C4B 113.5(6) . . ?
C3B C4B H4B 117.6 . . ?
C5B C4B C3B 124.7(7) . . ?
C5B C4B H4B 117.7 . . ?
C4B C5B H5B 121.7 . . ?
C4B C5B C6B 116.6(6) . . ?
C6B C5B H5B 121.7 . . ?
C5B C6B N1B 117.7(6) . . ?
C7B C6B N1B 118.3(7) . . ?
C7B C6B C5B 123.9(6) . . ?
C6B C7B H7B 121.4 . . ?
C6B C7B C8B 117.1(7) . . ?
C8B C7B H7B 121.4 . . ?
C3B C8B C7B 123.9(6) . . ?
C3B C8B H8B 118.1 . . ?
C7B C8B H8B 118.0 . . ?
N1B C9B H9B 128.6 . . ?
C10B C9B N1B 102.9(6) . . ?
C10B C9B H9B 128.5 . . ?
O2B C10B C9B 110.6(7) . . ?
O3B C10B O2B 118.7(6) . . ?
O3B C10B C9B 130.6(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1A H1A O3A 0.82 2.01 2.826(11) 170.6 1_545 yes
C9A H9A O1B 0.93 2.55 3.432(11) 157.7 4_576 yes
O1C H1C O3C 0.82 1.99 2.739(6) 150.8 1_545 yes
C9C H9C O1D 0.93 2.58 3.436(9) 154.0 1_565 yes
O1D H1D O3D 0.82 2.19 2.756(6) 126.6 1_545 yes
C7D H7D O1C 0.93 2.52 3.319(10) 143.6 4_575 yes
C9D H9D O3C 0.93 2.57 3.375(9) 144.6 4_585 yes
C7B H7B O1A 0.93 2.63 3.380(13) 138.4 1_565 yes
C9B H9B O3A 0.93 2.50 3.321(11) 148.1 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A C1A C3A C4A 178.7(14) . . . . ?
O1A C1A C3A C8A -6.2(18) . . . . ?
N1A C6A C7A C8A -178.7(8) . . . . ?
N1A C9A C10A O2A -0.2(11) . . . . ?
N1A C9A C10A O3A -176.6(13) . . . . ?
N2A O2A C10A O3A -176.4(11) . . . . ?
N2A O2A C10A C9A 6.7(13) . . . . ?
N2A N1A C6A C5A 14.7(14) . . . . ?
N2A N1A C6A C7A -159.3(10) . . . . ?
N2A N1A C9A C10A -6.6(11) . . . . ?
C1A C3A C4A C5A 179.4(11) . . . . ?
C1A C3A C8A C7A -175.1(11) . . . . ?
C2A C1A C3A C4A -54.6(19) . . . . ?
C2A C1A C3A C8A 120.5(12) . . . . ?
C3A C4A C5A C6A -2.5(18) . . . . ?
C4A C3A C8A C7A 0.5(17) . . . . ?
C4A C5A C6A N1A -177.3(8) . . . . ?
C4A C5A C6A C7A -3.9(17) . . . . ?
C5A C6A C7A C8A 7.9(17) . . . . ?
C6A N1A N2A O2A -175.6(8) . . . . ?
C6A N1A C9A C10A 179.8(9) . . . . ?
C6A C7A C8A C3A -5.9(15) . . . . ?
C8A C3A C4A C5A 4.1(18) . . . . ?
C9A N1A N2A O2A 10.2(11) . . . . ?
C9A N1A C6A C5A -171.9(9) . . . . ?
C9A N1A C6A C7A 14.1(14) . . . . ?
C10A O2A N2A N1A -10.2(12) . . . . ?
O1C C1C C3C C4C -165.5(8) . . . . ?
O1C C1C C3C C8C 6.8(12) . . . . ?
N1C C6C C7C C8C -177.3(6) . . . . ?
N1C C9C C10C O2C -0.9(9) . . . . ?
N1C C9C C10C O3C -177.8(9) . . . . ?
N2C O2C C10C O3C -179.4(7) . . . . ?
N2C O2C C10C C9C 3.0(9) . . . . ?
N2C N1C C6C C5C -11.6(9) . . . . ?
N2C N1C C6C C7C 166.5(7) . . . . ?
N2C N1C C9C C10C -1.6(9) . . . . ?
C1C C3C C4C C5C -178.9(7) . . . . ?
C1C C3C C8C C7C -178.5(8) . . . . ?
C2C C1C C3C C4C 68.0(11) . . . . ?
C2C C1C C3C C8C -119.7(10) . . . . ?
C3C C4C C5C C6C -6.2(12) . . . . ?
C4C C3C C8C C7C -6.2(12) . . . . ?
C4C C5C C6C N1C 179.6(6) . . . . ?
C4C C5C C6C C7C 1.6(10) . . . . ?
C5C C6C C7C C8C 0.8(10) . . . . ?
C6C N1C N2C O2C 178.4(5) . . . . ?
C6C N1C C9C C10C -175.9(6) . . . . ?
C6C C7C C8C C3C 1.7(12) . . . . ?
C8C C3C C4C C5C 8.5(12) . . . . ?
C9C N1C N2C O2C 3.4(8) . . . . ?
C9C N1C C6C C5C 162.4(7) . . . . ?
C9C N1C C6C C7C -19.6(10) . . . . ?
C10C O2C N2C N1C -4.0(9) . . . . ?
O1D C1D C3D C4D 170.8(8) . . . . ?
O1D C1D C3D C8D -16.7(10) . . . . ?
N1D C6D C7D C8D -178.5(6) . . . . ?
N1D C9D C10D O2D -0.8(7) . . . . ?
N1D C9D C10D O3D -176.5(8) . . . . ?
N2D O2D C10D O3D 178.9(6) . . . . ?
N2D O2D C10D C9D 2.3(7) . . . . ?
N2D N1D C6D C5D 12.7(9) . . . . ?
N2D N1D C6D C7D -165.1(7) . . . . ?
N2D N1D C9D C10D -1.2(8) . . . . ?
C1D C3D C4D C5D 178.5(7) . . . . ?
C1D C3D C8D C7D -176.4(6) . . . . ?
C2D C1D C3D C4D -58.9(10) . . . . ?
C2D C1D C3D C8D 113.6(8) . . . . ?
C3D C4D C5D C6D -3.4(11) . . . . ?
C4D C3D C8D C7D -3.7(11) . . . . ?
C4D C5D C6D N1D -179.5(6) . . . . ?
C4D C5D C6D C7D -1.7(10) . . . . ?
C5D C6D C7D C8D 3.8(10) . . . . ?
C6D N1D N2D O2D 179.3(5) . . . . ?
C6D N1D C9D C10D -177.7(6) . . . . ?
C6D C7D C8D C3D -1.1(10) . . . . ?
C8D C3D C4D C5D 6.0(11) . . . . ?
C9D N1D N2D O2D 2.6(8) . . . . ?
C9D N1D C6D C5D -170.9(6) . . . . ?
C9D N1D C6D C7D 11.3(10) . . . . ?
C10D O2D N2D N1D -3.0(8) . . . . ?
O1B C1B C3B C4B 166.8(8) . . . . ?
O1B C1B C3B C8B -7.5(12) . . . . ?
N1B C6B C7B C8B 177.5(7) . . . . ?
N1B C9B C10B O2B 1.2(10) . . . . ?
N1B C9B C10B O3B -178.9(9) . . . . ?
N2B O2B C10B O3B 179.0(7) . . . . ?
N2B O2B C10B C9B -1.2(10) . . . . ?
N2B N1B C6B C5B 12.2(11) . . . . ?
N2B N1B C6B C7B -167.8(8) . . . . ?
N2B N1B C9B C10B -0.9(10) . . . . ?
C1B C3B C4B C5B -178.3(8) . . . . ?
C1B C3B C8B C7B 174.2(8) . . . . ?
C2B C1B C3B C4B -72.2(9) . . . . ?
C2B C1B C3B C8B 113.5(10) . . . . ?
C3B C4B C5B C6B 3.9(13) . . . . ?
C4B C3B C8B C7B -0.4(13) . . . . ?
C4B C5B C6B N1B 179.2(7) . . . . ?
C4B C5B C6B C7B -0.8(13) . . . . ?
C5B C6B C7B C8B -2.5(13) . . . . ?
C6B N1B N2B O2B 180.0(6) . . . . ?
C6B N1B C9B C10B 179.4(7) . . . . ?
C6B C7B C8B C3B 3.1(13) . . . . ?
C8B C3B C4B C5B -3.2(13) . . . . ?
C9B N1B N2B O2B 0.2(10) . . . . ?
C9B N1B C6B C5B -168.0(8) . . . . ?
C9B N1B C6B C7B 12.0(12) . . . . ?
C10B O2B N2B N1B 0.6(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.949
_oxdiff_exptl_absorpt_empirical_full_min 0.444
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.504(4)
2 0.496(4)

####################################################################### 
# 
# 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_shs_956_fldu_autored
_database_code_depnum_ccdc_archive 'CCDC 2430403'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry, Iasi
Romania
;
_audit_update_record             
;
2025-03-11 deposited with the CCDC.	2025-06-27 downloaded from the CCDC.
;
_audit_creation_date             2025-03-09
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C10 H8 N2 O3)'
_chemical_formula_sum            'C20 H16 N4 O6'
_chemical_formula_weight         408.37
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
_chemical_oxdiff_usercomment     FA_5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
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'

_cell_length_a                   19.8269(13)
_cell_length_b                   5.3804(4)
_cell_length_c                   9.1694(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.462(7)
_cell_angle_gamma                90
_cell_volume                     971.95(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1511
_cell_measurement_temperature    296.0(9)
_cell_measurement_theta_max      73.7680
_cell_measurement_theta_min      4.4730
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.137a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1039
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4077
_diffrn_reflns_point_group_measured_fraction_full 0.731
_diffrn_reflns_point_group_measured_fraction_max 0.731
_diffrn_reflns_theta_full        66.562
_diffrn_reflns_theta_max         66.562
_diffrn_reflns_theta_min         4.489
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.0(9)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  -7.00   0.50    5.00    --  -46.76  94.00 -61.00  130
  2  ω     -4.00  24.00   0.50    5.00    --  -46.76  94.00 -61.00   56
  3  ω     32.00  57.00   0.50    5.00    --   46.76 -94.00-171.00   50
  4  ω    -65.00 -22.00   0.50   10.00    --  -91.75  94.00 -61.00   86
  5  ω     65.00 103.00   0.50   10.00    --  106.68 -94.00-171.00   76
  6  ω    106.00 178.00   0.50   10.00    --  106.68  94.00 -61.00  144
  7  ω   -115.00 -37.00   0.50    5.00    --  -46.76 -57.00-180.00  156
  8  ω    -28.00   0.00   0.50    5.00    --   46.76 -19.00 -90.00   56
  9  ω    -10.00  20.00   0.50    5.00    --   46.76 -19.00-180.00   60
 10  ω    -49.00 -20.00   0.50   10.00    --  -91.75  45.00 -90.00   58
 11  ω    -64.00 -37.00   0.50   10.00    --  -91.75  61.00  60.00   54
 12  ω   -157.00-101.00   0.50   10.00    --  -91.75 -95.00-120.00  112
 13  ω   -136.00-106.00   0.50   10.00    --  -91.75 -94.00-171.00   60
 14  ω    -49.00 -22.00   0.50   10.00    --  -91.75  45.00 150.00   54
 15  ω    -62.00 -37.00   0.50   10.00    --  -91.75  61.00 -60.00   50
 16  ω     35.00  62.00   0.50   10.00    --  106.68 -95.00 150.00   54
 17  ω     37.00  71.00   0.50   10.00    --  106.68 -61.00 -90.00   68
 18  ω     41.00  71.00   0.50   10.00    --  106.68 -61.00  60.00   60
 19  ω     43.00 103.00   0.50   10.00    --  106.68 -95.00-120.00  120
 20  ω     73.00 100.00   0.50   10.00    --  106.68 -95.00 150.00   54
 21  ω     37.00  71.00   0.50   10.00    --  106.68 -61.00  30.00   68
 22  ω     41.00 107.00   0.50   10.00    --  106.68-125.00  60.00  132
 23  ω     37.00  71.00   0.50   10.00    --  106.68 -61.00   0.00   68
 24  ω     40.00  70.00   0.50   10.00    --  106.68 -61.00-180.00   60
 25  ω     86.00 112.00   0.50    5.00    --   47.64  57.00-150.00   52
 26  ω    -14.00  24.00   0.50    5.00    --  -47.64  19.00 -30.00   76
 27  ω   -114.00 -88.00   0.50    5.00    --  -47.64 -38.00-150.00   52
 28  ω    -77.00 -51.00   0.50    5.00    --  -47.64 -38.00-150.00   52
 29  ω    -22.00   4.00   0.50    5.00    --   47.64 -19.00-120.00   52
 30  ω   -157.00-130.00   0.50   10.00    --  -91.75 -30.00  60.00   54
 31  ω    -45.00 -20.00   0.50   10.00    --  -91.75  45.00 -60.00   50
 32  ω    -51.00 -26.00   0.50   10.00    --  -91.75  45.00-150.00   50
 33  ω   -164.00-134.00   0.50   10.00    --  -91.75 -30.00  90.00   60
 34  ω   -114.00 -73.00   0.50   10.00    --  -91.75 -77.00-120.00   82
 35  ω   -107.00 -75.00   0.50   10.00    --  -91.75 -61.00-120.00   64
 36  ω   -126.00 -79.00   0.50   10.00    --  -91.75 -30.00  60.00   94
 37  ω    -51.00 -25.00   0.50   10.00    --  -91.75  45.00-120.00   52
 38  ω   -131.00 -82.00   0.50   10.00    --  -91.75 -30.00  90.00   98
 39  ω   -158.00-120.00   0.50   10.00    --  -91.75 -45.00-150.00   76
 40  ω    -51.00 -26.00   0.50   10.00    --  -91.75  45.00 -30.00   50
 41  ω     66.00  91.00   0.50   10.00    --  106.68 -77.00 120.00   50
 42  ω    153.00 178.00   0.50   10.00    --  106.68  30.00   0.00   50
 43  ω     35.00  78.00   0.50   10.00    --  106.68 -95.00   0.00   86
 44  ω    119.00 145.00   0.50   10.00    --  106.68  30.00   0.00   52
 45  ω     65.00  91.00   0.50   10.00    --  106.68 -95.00 -90.00   52
 46  ω     85.00 111.00   0.50   10.00    --  106.68-125.00 -30.00   52
 47  ω     34.00  62.00   0.50   10.00    --  106.68 -95.00 -90.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0323905000
_diffrn_orient_matrix_UB_12      0.1167651000
_diffrn_orient_matrix_UB_13      -0.1445924000
_diffrn_orient_matrix_UB_21      -0.0154439000
_diffrn_orient_matrix_UB_22      0.2384568000
_diffrn_orient_matrix_UB_23      0.0833412000
_diffrn_orient_matrix_UB_31      0.0694325000
_diffrn_orient_matrix_UB_32      0.1073373000
_diffrn_orient_matrix_UB_33      -0.0274806000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.467
_reflns_Friedel_fraction_full    0.466
_reflns_Friedel_fraction_max     0.466
_reflns_number_gt                1026
_reflns_number_total             1260
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.137a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.137a 64-bit (release 10-09-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.137a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1260
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0823
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1817P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2312
_refine_ls_wR_factor_ref         0.2494
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7112(3) 0.4012(11) 0.6907(7) 0.0886(19) Uani 1 1 d . . . . .
O2 O 0.8102(3) 0.5737(12) 0.6414(7) 0.0912(19) Uani 1 1 d . . . . .
O3 O 0.6609(3) 1.0638(9) 0.3897(7) 0.0791(16) Uani 1 1 d . . . . .
N1 N 0.6388(3) 0.6343(10) 0.5710(6) 0.0653(14) Uani 1 1 d . . . . .
N2 N 0.6440(4) 0.4384(13) 0.6559(8) 0.083(2) Uani 1 1 d . . . . .
C1 C 0.5699(4) 0.7036(13) 0.5170(8) 0.0668(17) Uani 1 1 d . . . . .
C2 C 0.5405(4) 0.9057(15) 0.5774(11) 0.082(2) Uani 1 1 d . . . . .
H2 H 0.564335 1.000134 0.650898 0.099 Uiso 1 1 calc R U . . .
C3 C 0.4749(4) 0.962(2) 0.5253(13) 0.097(3) Uani 1 1 d . . . . .
H3 H 0.453833 1.096918 0.564920 0.116 Uiso 1 1 calc R U . . .
C4 C 0.4397(5) 0.825(2) 0.4162(13) 0.104(4) Uani 1 1 d . . . . .
H4 H 0.395717 0.870455 0.379532 0.125 Uiso 1 1 calc R U . . .
C5 C 0.4699(6) 0.620(2) 0.3614(12) 0.103(3) Uani 1 1 d . . . . .
H5 H 0.445495 0.522088 0.290634 0.124 Uiso 1 1 calc R U . . .
C6 C 0.5355(5) 0.5608(16) 0.4101(10) 0.086(2) Uani 1 1 d . . . . .
H6 H 0.556388 0.425150 0.371173 0.103 Uiso 1 1 calc R U . . .
C7 C 0.6985(3) 0.7321(13) 0.5436(7) 0.0609(15) Uani 1 1 d . . . . .
C8 C 0.7508(4) 0.5823(14) 0.6236(8) 0.0712(19) Uani 1 1 d . . . . .
C9 C 0.7085(4) 0.9472(13) 0.4516(8) 0.0688(19) Uani 1 1 d . . . . .
C10 C 0.7807(4) 1.012(2) 0.4358(12) 0.090(2) Uani 1 1 d . . . . .
H10A H 0.800784 0.881397 0.383893 0.135 Uiso 1 1 calc R U . . .
H10B H 0.805415 1.031179 0.531330 0.135 Uiso 1 1 calc R U . . .
H10C H 0.782121 1.164598 0.382148 0.135 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.351(10) . ?
O1 C8 1.432(11) . ?
O2 C8 1.173(10) . ?
O3 C9 1.220(9) . ?
N1 N2 1.307(9) . ?
N1 C1 1.448(10) . ?
N1 C7 1.345(9) . ?
C1 C2 1.379(11) . ?
C1 C6 1.367(12) . ?
C2 C3 1.367(13) . ?
C3 C4 1.369(17) . ?
C4 C5 1.377(16) . ?
C5 C6 1.365(14) . ?
C7 C8 1.445(11) . ?
C7 C9 1.458(10) . ?
C9 C10 1.495(12) . ?

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
N2 O1 C8 111.8(6) . . ?
N2 N1 C1 114.7(6) . . ?
N2 N1 C7 114.5(7) . . ?
C7 N1 C1 130.7(6) . . ?
N1 N2 O1 105.6(6) . . ?
C2 C1 N1 119.5(6) . . ?
C6 C1 N1 118.4(7) . . ?
C6 C1 C2 122.1(8) . . ?
C3 C2 C1 117.7(9) . . ?
C2 C3 C4 121.5(11) . . ?
C3 C4 C5 119.3(9) . . ?
C6 C5 C4 120.5(9) . . ?
C5 C6 C1 118.9(9) . . ?
N1 C7 C8 106.4(7) . . ?
N1 C7 C9 126.7(6) . . ?
C8 C7 C9 126.8(6) . . ?
O1 C8 C7 101.6(7) . . ?
O2 C8 O1 120.2(7) . . ?
O2 C8 C7 138.1(8) . . ?
O3 C9 C7 121.9(7) . . ?
O3 C9 C10 122.3(7) . . ?
C7 C9 C10 115.7(7) . . ?


_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT340_shs_956_fldu_autored 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01244 Ang.
RESPONSE: A consiquence of the low quality of the crystal
;
# end Validation Reply Form

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.308
_oxdiff_exptl_absorpt_empirical_full_min 0.264
