# Supplementary Information (SI) for RSC Advances.
# 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_1F
_database_code_depnum_ccdc_archive 'CCDC 2418794'
loop_
_audit_author_name
_audit_author_address
'Talal Alazemi'
;Kuwait Univeristy
Kuwait
;
_audit_update_record             
;
2025-01-22 deposited with the CCDC.	2025-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H52 F N5 O4'
_chemical_formula_weight         565.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 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, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   10.0669(16)
_cell_length_b                   8.2576(13)
_cell_length_c                   20.700(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.747(7)
_cell_angle_gamma                90
_cell_volume                     1719.9(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6640
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      24.93

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.092
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.614
_exptl_absorpt_correction_T_max  0.996
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            12567
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.157
_diffrn_reflns_theta_max         24.936
_diffrn_reflns_theta_full        24.936
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3005
_reflns_number_gt                2015
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0600P)²+0.1001P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3005
_refine_ls_number_parameters     200
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1220
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
F1 F 0.500000 0.31867(18) 0.250000 0.0716(4) Uani 1 2 d S T P . .
O1 O 0.56366(12) 0.46550(16) 0.41796(6) 0.0701(4) Uani 1 1 d . . . . .
O2 O 0.30312(17) 0.2232(2) 0.16793(12) 0.1038(6) Uani 1 1 d D . . . .
N1 N 0.35309(15) 0.4258(2) 0.45918(8) 0.0634(4) Uani 1 1 d . . . . .
N2 N 0.37923(15) 0.38526(18) 0.35587(7) 0.0581(4) Uani 1 1 d . . . . .
N3 N 0.500000 0.8172(2) 0.250000 0.0621(6) Uani 1 2 d S T P . .
C1 C 0.44367(18) 0.4286(2) 0.41179(8) 0.0569(4) Uani 1 1 d . . . . .
C2 C 0.23042(17) 0.3780(2) 0.43327(9) 0.0615(5) Uani 1 1 d . . . . .
C3 C 0.1095(2) 0.3518(3) 0.46105(10) 0.0843(6) Uani 1 1 d . . . . .
H3 H 0.097800 0.369546 0.504877 0.101 Uiso 1 1 calc R U . . .
C4 C 0.0064(2) 0.2981(3) 0.42083(12) 0.0972(8) Uani 1 1 d . . . . .
H4 H -0.076471 0.279390 0.438021 0.117 Uiso 1 1 calc R U . . .
C5 C 0.0236(2) 0.2718(3) 0.35616(12) 0.0908(7) Uani 1 1 d . . . . .
H5 H -0.047864 0.235211 0.330621 0.109 Uiso 1 1 calc R U . . .
C6 C 0.1445(2) 0.2982(2) 0.32803(10) 0.0734(5) Uani 1 1 d . . . . .
H6 H 0.155878 0.280759 0.284154 0.088 Uiso 1 1 calc R U . . .
C7 C 0.24710(17) 0.3515(2) 0.36789(8) 0.0571(4) Uani 1 1 d . . . . .
C8 C 0.45279(18) 0.9269(2) 0.30388(9) 0.0673(5) Uani 1 1 d . . . . .
H8A H 0.526183 0.996000 0.317735 0.081 Uiso 1 1 calc R U . . .
H8B H 0.383027 0.996420 0.286221 0.081 Uiso 1 1 calc R U . . .
C9 C 0.4007(2) 0.8414(2) 0.36290(10) 0.0779(6) Uani 1 1 d . . . . .
H9A H 0.327100 0.771761 0.349754 0.094 Uiso 1 1 calc R U . . .
H9B H 0.470319 0.773667 0.381811 0.094 Uiso 1 1 calc R U . . .
C10 C 0.3550(3) 0.9591(3) 0.41265(12) 0.1023(8) Uani 1 1 d . . . . .
H10A H 0.428548 1.030015 0.424592 0.123 Uiso 1 1 calc R U . . .
H10B H 0.285025 1.025686 0.393364 0.123 Uiso 1 1 calc R U . . .
C11 C 0.3045(3) 0.8830(4) 0.47255(14) 0.1266(10) Uani 1 1 d . . . . .
H11A H 0.270685 0.965563 0.500258 0.152 Uiso 1 1 calc R U . . .
H11B H 0.375685 0.826449 0.494695 0.152 Uiso 1 1 calc R U . . .
H11C H 0.234711 0.808093 0.461206 0.152 Uiso 1 1 calc R U . . .
C12 C 0.61196(18) 0.7080(2) 0.27486(10) 0.0657(5) Uani 1 1 d . . . . .
H12A H 0.636801 0.636693 0.240009 0.079 Uiso 1 1 calc R U . . .
H12B H 0.578138 0.640720 0.309060 0.079 Uiso 1 1 calc R U . . .
C13 C 0.73652(19) 0.7934(2) 0.30061(12) 0.0799(6) Uani 1 1 d . . . . .
H13A H 0.772901 0.859228 0.266614 0.096 Uiso 1 1 calc R U . . .
H13B H 0.713471 0.864682 0.335786 0.096 Uiso 1 1 calc R U . . .
C14 C 0.8396(2) 0.6746(3) 0.32427(13) 0.0944(7) Uani 1 1 d . . . . .
H14A H 0.861685 0.603270 0.288960 0.113 Uiso 1 1 calc R U . . .
H14B H 0.802333 0.608691 0.358019 0.113 Uiso 1 1 calc R U . . .
C15 C 0.9656(2) 0.7540(3) 0.35043(15) 0.1134(9) Uani 1 1 d . . . . .
H15A H 1.006192 0.814032 0.316557 0.136 Uiso 1 1 calc R U . . .
H15B H 1.026011 0.672300 0.366308 0.136 Uiso 1 1 calc R U . . .
H15C H 0.944457 0.826167 0.385008 0.136 Uiso 1 1 calc R U . . .
H2A H 0.360(2) 0.254(4) 0.1955(12) 0.142(12) Uiso 1 1 d D . . . .
H2B H 0.325(5) 0.286(5) 0.1388(18) 0.28(3) Uiso 1 1 d D . . . .
H1 H 0.3689(18) 0.462(2) 0.4974(10) 0.070(6) Uiso 1 1 d . . . . .
H2 H 0.4250(17) 0.364(2) 0.3172(10) 0.070(5) Uiso 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
O1 C1 1.248(2) . ?
O2 H2A 0.838(10) . ?
O2 H2B 0.831(10) . ?
N1 C1 1.360(2) . ?
N1 C2 1.389(2) . ?
N1 H1 0.86(2) . ?
N2 C1 1.358(2) . ?
N2 C7 1.389(2) . ?
N2 H2 0.95(2) . ?
N3 C12 1.521(2) 2_655 ?
N3 C12 1.521(2) . ?
N3 C8 1.524(2) . ?
N3 C8 1.524(2) 2_655 ?
C2 C3 1.379(3) . ?
C2 C7 1.386(2) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(3) . ?
C6 H6 0.9300 . ?
C8 C9 1.518(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.499(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.493(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.521(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.499(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.513(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
H2A O2 H2B 96(4) . . ?
C1 N1 C2 109.53(16) . . ?
C1 N1 H1 123.4(13) . . ?
C2 N1 H1 126.5(13) . . ?
C1 N2 C7 109.61(15) . . ?
C1 N2 H2 122.3(11) . . ?
C7 N2 H2 127.2(11) . . ?
C12 N3 C12 107.29(17) 2_655 . ?
C12 N3 C8 110.83(10) 2_655 . ?
C12 N3 C8 110.44(11) . . ?
C12 N3 C8 110.44(11) 2_655 2_655 ?
C12 N3 C8 110.82(10) . 2_655 ?
C8 N3 C8 107.06(18) . 2_655 ?
O1 C1 N2 125.95(17) . . ?
O1 C1 N1 126.76(16) . . ?
N2 C1 N1 107.28(17) . . ?
C3 C2 C7 121.14(18) . . ?
C3 C2 N1 132.01(18) . . ?
C7 C2 N1 106.82(15) . . ?
C2 C3 C4 117.0(2) . . ?
C2 C3 H3 121.5 . . ?
C4 C3 H3 121.5 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 121.6(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 116.9(2) . . ?
C7 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
C6 C7 C2 121.70(17) . . ?
C6 C7 N2 131.52(17) . . ?
C2 C7 N2 106.76(15) . . ?
C9 C8 N3 115.82(15) . . ?
C9 C8 H8A 108.3 . . ?
N3 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
N3 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C8 111.85(17) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 114.7(2) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C13 116.02(14) . . ?
N3 C12 H12A 108.3 . . ?
C13 C12 H12A 108.3 . . ?
N3 C12 H12B 108.3 . . ?
C13 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C14 C13 C12 111.50(17) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 113.4(2) . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
C7 N2 C1 O1 179.44(16) . . . . ?
C7 N2 C1 N1 -1.16(19) . . . . ?
C2 N1 C1 O1 -179.75(17) . . . . ?
C2 N1 C1 N2 0.9(2) . . . . ?
C1 N1 C2 C3 177.8(2) . . . . ?
C1 N1 C2 C7 -0.2(2) . . . . ?
C7 C2 C3 C4 0.1(3) . . . . ?
N1 C2 C3 C4 -177.7(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
C5 C6 C7 N2 178.21(19) . . . . ?
C3 C2 C7 C6 0.0(3) . . . . ?
N1 C2 C7 C6 178.25(17) . . . . ?
C3 C2 C7 N2 -178.74(18) . . . . ?
N1 C2 C7 N2 -0.5(2) . . . . ?
C1 N2 C7 C6 -177.54(19) . . . . ?
C1 N2 C7 C2 1.0(2) . . . . ?
C12 N3 C8 C9 59.3(2) 2_655 . . . ?
C12 N3 C8 C9 -59.41(19) . . . . ?
C8 N3 C8 C9 179.8(2) 2_655 . . . ?
N3 C8 C9 C10 -179.21(18) . . . . ?
C8 C9 C10 C11 -179.0(2) . . . . ?
C12 N3 C12 C13 178.5(2) 2_655 . . . ?
C8 N3 C12 C13 -60.6(2) . . . . ?
C8 N3 C12 C13 57.8(2) 2_655 . . . ?
N3 C12 C13 C14 179.52(17) . . . . ?
C12 C13 C14 C15 -180.0(2) . . . . ?

_refine_diff_density_max         0.123
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.024



####################################################################### 
# 
# 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 2418801'
loop_
_audit_author_name
_audit_author_address
'Talal Alazemi'
;Kuwait Univeristy
Kuwait
;
_audit_update_record             
;
2025-01-22 deposited with the CCDC.	2025-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N6 O6'
_chemical_formula_weight         436.39

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   38.788(3)
_cell_length_b                   4.5685(4)
_cell_length_c                   11.1314(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1972.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4604
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      24.99

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_T_max  0.996
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            9726
_diffrn_reflns_av_unetI/netI     0.1241
_diffrn_reflns_av_R_equivalents  0.1172
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.645
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.019
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3481
_reflns_number_gt                1851
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0309P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3481
_refine_ls_number_parameters     305
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1371
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_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
O1 O 0.11032(12) 0.0833(8) 1.1638(5) 0.0555(14) Uani 1 1 d . . . . .
O2 O 0.20822(15) -0.1794(15) 0.9442(6) 0.103(3) Uani 1 1 d . . . . .
O3 O 0.25898(14) -0.1706(13) 1.0182(6) 0.091(2) Uani 1 1 d . . . . .
O4 O 0.06932(14) 0.2539(10) 0.8843(5) 0.0736(17) Uani 1 1 d . . . . .
O5 O 0.09217(17) 0.0118(14) 0.4745(6) 0.090(2) Uani 1 1 d . . . . .
O6 O 0.14559(18) -0.0178(13) 0.4256(6) 0.091(2) Uani 1 1 d . . . . .
N1 N 0.08118(15) 0.5091(12) 1.1840(6) 0.0490(16) Uani 1 1 d D . . . .
N2 N 0.13942(16) 0.5016(14) 1.2053(7) 0.056(2) Uani 1 1 d . . . . .
N3 N 0.22901(19) -0.0990(14) 1.0196(6) 0.0627(19) Uani 1 1 d . . . . .
N4 N 0.04735(16) 0.6575(13) 0.9712(6) 0.0498(17) Uani 1 1 d . . . . .
N5 N 0.08881(16) 0.6970(13) 0.8253(6) 0.0491(16) Uani 1 1 d D . . . .
N6 N 0.1227(2) 0.0806(15) 0.4870(6) 0.0648(19) Uani 1 1 d . . . . .
C1 C 0.04786(16) 0.3954(14) 1.1610(7) 0.0407(18) Uani 1 1 d . . . . .
C2 C 0.03288(19) 0.2038(15) 1.2401(7) 0.049(2) Uani 1 1 d . . . . .
H2A H 0.044667 0.145781 1.308895 0.059 Uiso 1 1 calc R U . . .
C3 C 0.0001(2) 0.0969(15) 1.2172(7) 0.059(2) Uani 1 1 d . . . . .
H3 H -0.009835 -0.038211 1.269323 0.071 Uiso 1 1 calc R U . . .
C4 C -0.01770(19) 0.1895(17) 1.1183(8) 0.062(2) Uani 1 1 d . . . . .
H4A H -0.040044 0.123157 1.105017 0.074 Uiso 1 1 calc R U . . .
C5 C -0.00272(18) 0.3802(16) 1.0385(7) 0.052(2) Uani 1 1 d . . . . .
H5A H -0.014782 0.441305 0.970843 0.062 Uiso 1 1 calc R U . . .
C6 C 0.03052(17) 0.4816(14) 1.0593(6) 0.0386(17) Uani 1 1 d . . . . .
C7 C 0.11024(18) 0.3471(13) 1.1827(7) 0.0441(18) Uani 1 1 d . . . . .
C8 C 0.17309(18) 0.3920(13) 1.2009(7) 0.0419(18) Uani 1 1 d . . . . .
C9 C 0.18359(17) 0.1921(15) 1.1143(6) 0.0438(19) Uani 1 1 d . . . . .
H9 H 0.167898 0.119649 1.058563 0.053 Uiso 1 1 calc R U . . .
C10 C 0.21735(18) 0.1027(15) 1.1118(7) 0.0463(19) Uani 1 1 d . . . . .
C11 C 0.24125(18) 0.2009(15) 1.1940(7) 0.052(2) Uani 1 1 d . . . . .
H11 H 0.263874 0.133795 1.192003 0.062 Uiso 1 1 calc R U . . .
C12 C 0.2309(2) 0.3999(16) 1.2787(7) 0.058(2) Uani 1 1 d . . . . .
H12 H 0.246671 0.470600 1.334468 0.070 Uiso 1 1 calc R U . . .
C13 C 0.1972(2) 0.4962(16) 1.2821(7) 0.053(2) Uani 1 1 d . . . . .
H13 H 0.190616 0.632974 1.339509 0.063 Uiso 1 1 calc R U . . .
C14 C 0.06873(19) 0.5227(15) 0.8939(7) 0.0472(19) Uani 1 1 d . . . . .
C15 C 0.11438(19) 0.5872(15) 0.7447(6) 0.0432(18) Uani 1 1 d . . . . .
C16 C 0.10545(18) 0.3882(14) 0.6560(7) 0.0438(18) Uani 1 1 d . . . . .
H16 H 0.082889 0.322543 0.647352 0.053 Uiso 1 1 calc R U . . .
C17 C 0.1314(2) 0.2916(16) 0.5811(7) 0.0489(19) Uani 1 1 d . . . . .
C18 C 0.1650(2) 0.3783(17) 0.5939(8) 0.062(2) Uani 1 1 d . . . . .
H18 H 0.181991 0.304744 0.543352 0.074 Uiso 1 1 calc R U . . .
C19 C 0.17312(19) 0.5747(18) 0.6823(9) 0.066(2) Uani 1 1 d . . . . .
H19 H 0.195833 0.636059 0.691437 0.079 Uiso 1 1 calc R U . . .
C20 C 0.1481(2) 0.6819(16) 0.7575(7) 0.058(2) Uani 1 1 d . . . . .
H20 H 0.153813 0.817325 0.816657 0.069 Uiso 1 1 calc R U . . .
H1 H 0.0830(16) 0.695(5) 1.172(7) 0.06(2) Uiso 1 1 d D . . . .
H2 H 0.1383(19) 0.679(15) 1.224(6) 0.06(3) Uiso 1 1 d . . . . .
H5 H 0.094(2) 0.875(9) 0.848(9) 0.12(4) Uiso 1 1 d D . . . .
H4 H 0.0457(19) 0.856(17) 0.986(7) 0.09(3) Uiso 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
O1 C7 1.223(6) . ?
O2 N3 1.220(7) . ?
O3 N3 1.208(7) . ?
O4 C14 1.233(7) . ?
O5 N6 1.232(8) . ?
O6 N6 1.208(8) . ?
N1 C7 1.349(8) . ?
N1 C1 1.416(8) . ?
N1 H1 0.864(15) . ?
N2 C7 1.357(8) . ?
N2 C8 1.400(8) . ?
N2 H2 0.84(7) . ?
N3 C10 1.451(9) . ?
N4 C14 1.345(8) . ?
N4 C6 1.426(8) . ?
N4 H4 0.92(8) . ?
N5 C14 1.350(8) . ?
N5 C15 1.429(9) . ?
N5 H5 0.876(15) . ?
N6 C17 1.463(10) . ?
C1 C2 1.371(9) . ?
C1 C6 1.375(9) . ?
C2 C3 1.386(10) . ?
C2 H2A 0.9300 . ?
C3 C4 1.366(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(9) . ?
C4 H4A 0.9300 . ?
C5 C6 1.389(8) . ?
C5 H5A 0.9300 . ?
C8 C13 1.385(9) . ?
C8 C9 1.389(9) . ?
C9 C10 1.372(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(9) . ?
C11 C12 1.371(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(10) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C15 C16 1.386(9) . ?
C15 C20 1.387(10) . ?
C16 C17 1.378(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(9) . ?
C18 C19 1.369(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(10) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
C7 N1 C1 124.0(6) . . ?
C7 N1 H1 118(4) . . ?
C1 N1 H1 114(4) . . ?
C7 N2 C8 125.9(6) . . ?
C7 N2 H2 120(5) . . ?
C8 N2 H2 114(5) . . ?
O3 N3 O2 123.1(6) . . ?
O3 N3 C10 118.7(7) . . ?
O2 N3 C10 118.1(6) . . ?
C14 N4 C6 117.7(6) . . ?
C14 N4 H4 128(5) . . ?
C6 N4 H4 113(5) . . ?
C14 N5 C15 123.3(6) . . ?
C14 N5 H5 121(7) . . ?
C15 N5 H5 111(7) . . ?
O6 N6 O5 123.2(7) . . ?
O6 N6 C17 118.7(8) . . ?
O5 N6 C17 118.0(7) . . ?
C2 C1 C6 120.3(6) . . ?
C2 C1 N1 120.3(8) . . ?
C6 C1 N1 119.4(7) . . ?
C1 C2 C3 119.7(7) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C4 C3 C2 120.2(7) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.3(7) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 119.8(7) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C1 C6 C5 119.7(6) . . ?
C1 C6 N4 120.3(6) . . ?
C5 C6 N4 119.9(7) . . ?
O1 C7 N1 123.0(6) . . ?
O1 C7 N2 122.8(6) . . ?
N1 C7 N2 114.2(5) . . ?
C13 C8 C9 118.7(7) . . ?
C13 C8 N2 119.0(7) . . ?
C9 C8 N2 122.2(7) . . ?
C10 C9 C8 119.3(6) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 122.1(6) . . ?
C9 C10 N3 120.1(6) . . ?
C11 C10 N3 117.8(6) . . ?
C12 C11 C10 118.4(7) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C13 120.6(7) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 120.9(7) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
O4 C14 N4 121.5(7) . . ?
O4 C14 N5 121.8(7) . . ?
N4 C14 N5 116.6(6) . . ?
C16 C15 C20 120.9(7) . . ?
C16 C15 N5 120.3(7) . . ?
C20 C15 N5 118.8(7) . . ?
C17 C16 C15 117.3(7) . . ?
C17 C16 H16 121.3 . . ?
C15 C16 H16 121.3 . . ?
C18 C17 C16 122.6(7) . . ?
C18 C17 N6 118.9(7) . . ?
C16 C17 N6 118.4(7) . . ?
C19 C18 C17 118.9(7) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 120.7(8) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 119.6(8) . . ?
C19 C20 H20 120.2 . . ?
C15 C20 H20 120.2 . . ?

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
C7 N1 C1 C2 67.7(10) . . . . ?
C7 N1 C1 C6 -113.1(8) . . . . ?
C6 C1 C2 C3 0.0(10) . . . . ?
N1 C1 C2 C3 179.2(6) . . . . ?
C1 C2 C3 C4 -2.2(10) . . . . ?
C2 C3 C4 C5 2.5(11) . . . . ?
C3 C4 C5 C6 -0.7(11) . . . . ?
C2 C1 C6 C5 1.8(10) . . . . ?
N1 C1 C6 C5 -177.4(6) . . . . ?
C2 C1 C6 N4 -173.8(6) . . . . ?
N1 C1 C6 N4 7.0(9) . . . . ?
C4 C5 C6 C1 -1.5(10) . . . . ?
C4 C5 C6 N4 174.1(6) . . . . ?
C14 N4 C6 C1 79.5(8) . . . . ?
C14 N4 C6 C5 -96.1(8) . . . . ?
C1 N1 C7 O1 -1.6(13) . . . . ?
C1 N1 C7 N2 178.9(7) . . . . ?
C8 N2 C7 O1 5.3(14) . . . . ?
C8 N2 C7 N1 -175.2(7) . . . . ?
C7 N2 C8 C13 -144.7(8) . . . . ?
C7 N2 C8 C9 38.4(12) . . . . ?
C13 C8 C9 C10 0.3(10) . . . . ?
N2 C8 C9 C10 177.2(7) . . . . ?
C8 C9 C10 C11 1.1(11) . . . . ?
C8 C9 C10 N3 -178.1(7) . . . . ?
O3 N3 C10 C9 178.8(8) . . . . ?
O2 N3 C10 C9 1.6(11) . . . . ?
O3 N3 C10 C11 -0.4(11) . . . . ?
O2 N3 C10 C11 -177.7(7) . . . . ?
C9 C10 C11 C12 -1.7(11) . . . . ?
N3 C10 C11 C12 177.6(7) . . . . ?
C10 C11 C12 C13 0.7(11) . . . . ?
C11 C12 C13 C8 0.7(12) . . . . ?
C9 C8 C13 C12 -1.2(11) . . . . ?
N2 C8 C13 C12 -178.2(7) . . . . ?
C6 N4 C14 O4 12.7(11) . . . . ?
C6 N4 C14 N5 -168.9(6) . . . . ?
C15 N5 C14 O4 -5.8(12) . . . . ?
C15 N5 C14 N4 175.8(7) . . . . ?
C14 N5 C15 C16 55.9(10) . . . . ?
C14 N5 C15 C20 -123.7(8) . . . . ?
C20 C15 C16 C17 -0.5(9) . . . . ?
N5 C15 C16 C17 179.9(7) . . . . ?
C15 C16 C17 C18 1.9(10) . . . . ?
C15 C16 C17 N6 179.8(6) . . . . ?
O6 N6 C17 C18 2.2(11) . . . . ?
O5 N6 C17 C18 -177.9(7) . . . . ?
O6 N6 C17 C16 -175.7(7) . . . . ?
O5 N6 C17 C16 4.1(11) . . . . ?
C16 C17 C18 C19 -1.9(12) . . . . ?
N6 C17 C18 C19 -179.7(7) . . . . ?
C17 C18 C19 C20 0.4(13) . . . . ?
C18 C19 C20 C15 0.8(12) . . . . ?
C16 C15 C20 C19 -0.8(11) . . . . ?
N5 C15 C20 C19 178.8(7) . . . . ?

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.041



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2418802'
loop_
_audit_author_name
_audit_author_address
'Talal Alazemi'
;Kuwait Univeristy
Kuwait
;
_audit_update_record             
;
2025-01-22 deposited with the CCDC.	2025-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N6 O6'
_chemical_formula_weight         436.39

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      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                   18.4683(10)
_cell_length_b                   12.2887(8)
_cell_length_c                   8.9483(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.464(7)
_cell_angle_gamma                90
_cell_volume                     1990.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4553
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      25.0

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_T_max  0.996
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            7210
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.233
_diffrn_reflns_theta_max         25.012
_diffrn_reflns_theta_full        25.012
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             3381
_reflns_number_gt                2082
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0665P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3381
_refine_ls_number_parameters     305
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1343
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.013
_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
O1 O 0.67039(9) 0.69750(13) 0.71315(18) 0.0589(5) Uani 1 1 d . . . . .
O2 O 0.55037(11) 0.63960(19) 0.1945(2) 0.0864(7) Uani 1 1 d . . . . .
O3 O 0.47341(12) 0.5090(2) 0.1487(3) 0.1275(10) Uani 1 1 d . . . . .
O4 O 0.85732(8) 0.82058(12) 1.04859(17) 0.0526(4) Uani 1 1 d . . . . .
O5 O 0.82670(11) 0.46653(17) 0.8321(3) 0.0949(8) Uani 1 1 d . . . . .
O6 O 0.85751(14) 0.32814(19) 0.9735(3) 0.1224(10) Uani 1 1 d . . . . .
N1 N 0.70017(10) 0.81084(17) 0.5338(2) 0.0492(5) Uani 1 1 d . . . . .
N2 N 0.64149(10) 0.65044(17) 0.4608(2) 0.0502(5) Uani 1 1 d . . . . .
N3 N 0.52671(11) 0.5514(2) 0.2274(3) 0.0721(7) Uani 1 1 d . . . . .
N4 N 0.81388(10) 0.80225(16) 0.7935(2) 0.0462(5) Uani 1 1 d . . . . .
N5 N 0.87416(11) 0.66168(17) 0.9254(2) 0.0557(6) Uani 1 1 d . . . . .
N6 N 0.86143(12) 0.4247(2) 0.9475(3) 0.0753(7) Uani 1 1 d . U . . .
C1 C 0.72058(11) 0.90430(19) 0.6260(3) 0.0464(6) Uani 1 1 d . . . . .
C2 C 0.68850(13) 1.0027(2) 0.5781(3) 0.0650(8) Uani 1 1 d . . . . .
H2 H 0.652820 1.006102 0.488836 0.078 Uiso 1 1 calc R U . . .
C3 C 0.70844(16) 1.0957(2) 0.6603(4) 0.0828(10) Uani 1 1 d . . . . .
H3 H 0.686959 1.161771 0.625566 0.099 Uiso 1 1 calc R U . . .
C4 C 0.75991(15) 1.0916(2) 0.7934(3) 0.0739(8) Uani 1 1 d . . . . .
H4 H 0.772115 1.154579 0.850505 0.089 Uiso 1 1 calc R U . . .
C5 C 0.79345(13) 0.99522(19) 0.8425(3) 0.0556(7) Uani 1 1 d . . . . .
H5A H 0.828116 0.992976 0.933379 0.067 Uiso 1 1 calc R U . . .
C6 C 0.77622(11) 0.90090(18) 0.7581(2) 0.0438(6) Uani 1 1 d . . . . .
C7 C 0.67075(11) 0.71852(19) 0.5793(3) 0.0462(6) Uani 1 1 d . . . . .
C8 C 0.61773(11) 0.5446(2) 0.4753(3) 0.0507(6) Uani 1 1 d . . . . .
C9 C 0.56329(12) 0.4944(2) 0.3646(3) 0.0570(7) Uani 1 1 d . . . . .
C10 C 0.54041(15) 0.3880(3) 0.3817(4) 0.0774(9) Uani 1 1 d . . . . .
H10 H 0.504235 0.357128 0.306438 0.093 Uiso 1 1 calc R U . . .
C11 C 0.57034(18) 0.3286(2) 0.5072(4) 0.0891(10) Uani 1 1 d . . . . .
H11 H 0.555007 0.257523 0.518730 0.107 Uiso 1 1 calc R U . . .
C12 C 0.62406(18) 0.3764(2) 0.6171(4) 0.0832(9) Uani 1 1 d . . . . .
H12 H 0.644687 0.337154 0.704019 0.100 Uiso 1 1 calc R U . . .
C13 C 0.64746(14) 0.4806(2) 0.6004(3) 0.0674(8) Uani 1 1 d . . . . .
H13 H 0.684575 0.509572 0.675506 0.081 Uiso 1 1 calc R U . . .
C14 C 0.84928(11) 0.76671(18) 0.9313(3) 0.0441(6) Uani 1 1 d . . . . .
C15 C 0.91576(12) 0.60338(19) 1.0454(3) 0.0503(6) Uani 1 1 d . . . . .
C16 C 0.91135(12) 0.4908(2) 1.0594(3) 0.0558(7) Uani 1 1 d . U . . .
C17 C 0.95415(16) 0.4357(2) 1.1798(4) 0.0761(9) Uani 1 1 d . . . . .
H17 H 0.949771 0.360575 1.186973 0.091 Uiso 1 1 calc R U . . .
C18 C 1.00274(16) 0.4907(3) 1.2880(4) 0.0843(10) Uani 1 1 d . . . . .
H18 H 1.031255 0.453590 1.369582 0.101 Uiso 1 1 calc R U . . .
C19 C 1.00911(15) 0.6006(3) 1.2755(3) 0.0795(9) Uani 1 1 d . . . . .
H19 H 1.042810 0.638141 1.348459 0.095 Uiso 1 1 calc R U . . .
C20 C 0.96696(13) 0.6569(2) 1.1577(3) 0.0637(7) Uani 1 1 d . . . . .
H20 H 0.972386 0.731918 1.152176 0.076 Uiso 1 1 calc R U . . .
H1 H 0.6924(13) 0.826(2) 0.443(3) 0.066(8) Uiso 1 1 d . . . . .
H5 H 0.6366(15) 0.682(2) 0.367(3) 0.082(9) Uiso 1 1 d . . . . .
H6 H 0.8187(13) 0.760(2) 0.718(3) 0.061(8) Uiso 1 1 d . . . . .
H7 H 0.8538(13) 0.620(2) 0.854(3) 0.068(9) Uiso 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
O1 C7 1.226(3) . ?
O2 N3 1.226(3) . ?
O3 N3 1.208(3) . ?
O4 C14 1.225(3) . ?
O5 N6 1.216(3) . ?
O6 N6 1.215(3) . ?
N1 C7 1.355(3) . ?
N1 C1 1.421(3) . ?
N1 H1 0.82(3) . ?
N2 C7 1.374(3) . ?
N2 C8 1.387(3) . ?
N2 H5 0.91(3) . ?
N3 C9 1.458(3) . ?
N4 C14 1.349(3) . ?
N4 C6 1.402(3) . ?
N4 H6 0.87(3) . ?
N5 C14 1.375(3) . ?
N5 C15 1.389(3) . ?
N5 H7 0.85(3) . ?
N6 C16 1.465(3) . ?
C1 C2 1.377(3) . ?
C1 C6 1.404(3) . ?
C2 C3 1.368(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5A 0.9300 . ?
C8 C13 1.389(3) . ?
C8 C9 1.406(3) . ?
C9 C10 1.392(4) . ?
C10 C11 1.362(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C15 C16 1.393(3) . ?
C15 C20 1.400(3) . ?
C16 C17 1.381(3) . ?
C17 C18 1.362(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.363(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.366(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
C7 N1 C1 125.3(2) . . ?
C7 N1 H1 119.5(18) . . ?
C1 N1 H1 111.1(18) . . ?
C7 N2 C8 125.6(2) . . ?
C7 N2 H5 113.6(17) . . ?
C8 N2 H5 120.7(17) . . ?
O3 N3 O2 122.0(3) . . ?
O3 N3 C9 118.1(3) . . ?
O2 N3 C9 119.9(2) . . ?
C14 N4 C6 128.0(2) . . ?
C14 N4 H6 114.3(16) . . ?
C6 N4 H6 117.5(17) . . ?
C14 N5 C15 126.4(2) . . ?
C14 N5 H7 119.9(17) . . ?
C15 N5 H7 111.2(18) . . ?
O6 N6 O5 122.3(3) . . ?
O6 N6 C16 117.6(3) . . ?
O5 N6 C16 120.0(2) . . ?
C2 C1 C6 119.0(2) . . ?
C2 C1 N1 118.8(2) . . ?
C6 C1 N1 122.0(2) . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 N4 123.4(2) . . ?
C5 C6 C1 119.0(2) . . ?
N4 C6 C1 117.6(2) . . ?
O1 C7 N1 123.4(2) . . ?
O1 C7 N2 123.2(2) . . ?
N1 C7 N2 113.4(2) . . ?
N2 C8 C13 121.6(2) . . ?
N2 C8 C9 122.7(2) . . ?
C13 C8 C9 115.6(2) . . ?
C10 C9 C8 121.6(3) . . ?
C10 C9 N3 116.3(2) . . ?
C8 C9 N3 122.0(2) . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 118.4(3) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C13 C12 C11 121.2(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C8 122.3(3) . . ?
C12 C13 H13 118.8 . . ?
C8 C13 H13 118.8 . . ?
O4 C14 N4 124.3(2) . . ?
O4 C14 N5 123.8(2) . . ?
N4 C14 N5 112.0(2) . . ?
N5 C15 C16 123.3(2) . . ?
N5 C15 C20 120.3(2) . . ?
C16 C15 C20 116.4(2) . . ?
C17 C16 C15 121.5(2) . . ?
C17 C16 N6 116.5(2) . . ?
C15 C16 N6 122.0(2) . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.3(3) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C20 121.3(3) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C15 121.1(3) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?

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
C7 N1 C1 C2 -121.8(3) . . . . ?
C7 N1 C1 C6 63.0(3) . . . . ?
C6 C1 C2 C3 -2.2(4) . . . . ?
N1 C1 C2 C3 -177.6(3) . . . . ?
C1 C2 C3 C4 -1.2(5) . . . . ?
C2 C3 C4 C5 2.1(5) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 N4 173.1(2) . . . . ?
C4 C5 C6 C1 -3.8(4) . . . . ?
C14 N4 C6 C5 27.6(3) . . . . ?
C14 N4 C6 C1 -155.4(2) . . . . ?
C2 C1 C6 C5 4.6(3) . . . . ?
N1 C1 C6 C5 179.8(2) . . . . ?
C2 C1 C6 N4 -172.5(2) . . . . ?
N1 C1 C6 N4 2.7(3) . . . . ?
C1 N1 C7 O1 -13.4(4) . . . . ?
C1 N1 C7 N2 166.7(2) . . . . ?
C8 N2 C7 O1 -9.7(4) . . . . ?
C8 N2 C7 N1 170.1(2) . . . . ?
C7 N2 C8 C13 -27.4(4) . . . . ?
C7 N2 C8 C9 153.5(2) . . . . ?
N2 C8 C9 C10 180.0(2) . . . . ?
C13 C8 C9 C10 0.9(4) . . . . ?
N2 C8 C9 N3 -1.2(4) . . . . ?
C13 C8 C9 N3 179.6(2) . . . . ?
O3 N3 C9 C10 9.3(4) . . . . ?
O2 N3 C9 C10 -170.5(3) . . . . ?
O3 N3 C9 C8 -169.5(3) . . . . ?
O2 N3 C9 C8 10.7(4) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
N3 C9 C10 C11 -178.9(3) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C11 C12 C13 C8 1.6(5) . . . . ?
N2 C8 C13 C12 179.3(3) . . . . ?
C9 C8 C13 C12 -1.6(4) . . . . ?
C6 N4 C14 O4 -4.4(4) . . . . ?
C6 N4 C14 N5 174.3(2) . . . . ?
C15 N5 C14 O4 -4.7(4) . . . . ?
C15 N5 C14 N4 176.5(2) . . . . ?
C14 N5 C15 C16 149.1(2) . . . . ?
C14 N5 C15 C20 -32.9(4) . . . . ?
N5 C15 C16 C17 179.4(3) . . . . ?
C20 C15 C16 C17 1.4(4) . . . . ?
N5 C15 C16 N6 -0.4(4) . . . . ?
C20 C15 C16 N6 -178.4(2) . . . . ?
O6 N6 C16 C17 4.9(4) . . . . ?
O5 N6 C16 C17 -173.9(3) . . . . ?
O6 N6 C16 C15 -175.3(3) . . . . ?
O5 N6 C16 C15 6.0(4) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
N6 C16 C17 C18 179.2(3) . . . . ?
C16 C17 C18 C19 -0.6(5) . . . . ?
C17 C18 C19 C20 1.0(5) . . . . ?
C18 C19 C20 C15 -0.2(5) . . . . ?
N5 C15 C20 C19 -179.1(3) . . . . ?
C16 C15 C20 C19 -1.0(4) . . . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.042



