# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

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

data_RSH_30012021
_database_code_depnum_ccdc_archive 'CCDC 2070229'
loop_
_audit_author_name
_audit_author_address
'ELANCHERAN R'
;Annamalai University
India
;
_audit_update_record             
;
2021-03-14 deposited with the CCDC.	2021-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            Organic
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 N6 O4'
_chemical_formula_sum            'C19 H16 N6 O4'
_chemical_formula_weight         392.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   7.6825(8)
_cell_length_b                   13.3272(13)
_cell_length_c                   18.012(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1844.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3504
_cell_measurement_theta_min      1.901
_cell_measurement_theta_max      28.422

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            clear
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6568
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       'Omega and Phi Scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            20256
_diffrn_reflns_av_unetI/netI     0.0785
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.901
_diffrn_reflns_theta_max         28.422
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4435
_reflns_number_gt                2574
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_max     0.928
_reflns_Friedel_fraction_full    0.975

_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       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'
_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)+0.1183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4435
_refine_ls_number_parameters     263
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.4108(4) 0.01553(19) 0.61617(15) 0.0783(8) Uani 1 1 d . . . . .
O2 O 0.3294(4) 0.32994(19) 0.52654(15) 0.0723(8) Uani 1 1 d . . . . .
O3 O -0.0387(5) 0.1125(3) -0.06218(19) 0.1033(11) Uani 1 1 d . . . . .
O4 O -0.0541(5) 0.2735(3) -0.06084(17) 0.0975(11) Uani 1 1 d . . . . .
N1 N 0.3649(4) 0.1624(2) 0.55228(14) 0.0535(7) Uani 1 1 d . . . . .
N2 N 0.3838(4) 0.1189(2) 0.28237(16) 0.0556(7) Uani 1 1 d . . . . .
N3 N 0.4603(4) 0.1592(2) 0.34075(16) 0.0545(7) Uani 1 1 d . . . . .
N4 N 0.4663(5) 0.2579(2) 0.33975(19) 0.0666(9) Uani 1 1 d . . . . .
N5 N 0.3889(5) 0.2852(2) 0.27769(19) 0.0681(9) Uani 1 1 d . . . . .
N6 N -0.0085(5) 0.1933(3) -0.03327(19) 0.0744(10) Uani 1 1 d . . . . .
C1 C 0.4256(5) 0.1052(3) 0.6116(2) 0.0565(9) Uani 1 1 d . . . . .
C2 C 0.5002(5) 0.1764(3) 0.66516(18) 0.0552(9) Uani 1 1 d . . . . .
C3 C 0.5797(5) 0.1597(3) 0.7321(2) 0.0665(10) Uani 1 1 d . . . . .
H3 H 0.598670 0.094929 0.749487 0.080 Uiso 1 1 calc R U . . .
C4 C 0.6303(6) 0.2418(4) 0.7725(2) 0.0804(13) Uani 1 1 d . . . . .
H4 H 0.685561 0.232767 0.817940 0.097 Uiso 1 1 calc R U . . .
C5 C 0.6005(6) 0.3370(4) 0.7466(3) 0.0805(13) Uani 1 1 d . . . . .
H5 H 0.634142 0.391443 0.775611 0.097 Uiso 1 1 calc R U . . .
C6 C 0.5214(5) 0.3547(3) 0.6785(2) 0.0696(11) Uani 1 1 d . . . . .
H6 H 0.502253 0.419370 0.660883 0.084 Uiso 1 1 calc R U . . .
C7 C 0.4731(4) 0.2716(3) 0.6385(2) 0.0525(8) Uani 1 1 d . . . . .
C8 C 0.3820(4) 0.2638(3) 0.5661(2) 0.0534(9) Uani 1 1 d . . . . .
C9 C 0.2724(5) 0.1187(3) 0.48896(19) 0.0620(10) Uani 1 1 d . . . . .
H9A H 0.230303 0.172320 0.457269 0.074 Uiso 1 1 calc R U . . .
H9AB H 0.172113 0.081747 0.506960 0.074 Uiso 1 1 calc R U . . .
C10 C 0.3864(5) 0.0488(3) 0.4435(2) 0.0627(10) Uani 1 1 d . . . . .
H10A H 0.435803 -0.001198 0.476466 0.075 Uiso 1 1 calc R U . . .
H10B H 0.313469 0.013914 0.407923 0.075 Uiso 1 1 calc R U . . .
C11 C 0.5327(5) 0.0993(3) 0.40208(19) 0.0571(9) Uani 1 1 d . . . . .
H11 H 0.592557 0.144807 0.436355 0.069 Uiso 1 1 calc R U . . .
C12 C 0.6649(6) 0.0249(3) 0.3722(2) 0.0717(11) Uani 1 1 d . . . . .
H12A H 0.606753 -0.023875 0.341814 0.108 Uiso 1 1 calc R U . . .
H12B H 0.721299 -0.008387 0.412924 0.108 Uiso 1 1 calc R U . . .
H12C H 0.750143 0.059800 0.343080 0.108 Uiso 1 1 calc R U . . .
C13 C 0.3398(5) 0.2002(3) 0.2434(2) 0.0544(9) Uani 1 1 d . . . . .
C14 C 0.2508(5) 0.1976(3) 0.1717(2) 0.0542(8) Uani 1 1 d . . . . .
C15 C 0.2179(5) 0.1075(3) 0.1368(2) 0.0630(9) Uani 1 1 d . . . . .
H15 H 0.252117 0.047748 0.159138 0.076 Uiso 1 1 calc R U . . .
C16 C 0.1342(5) 0.1053(3) 0.0686(2) 0.0657(10) Uani 1 1 d . . . . .
H16 H 0.111406 0.044836 0.044697 0.079 Uiso 1 1 calc R U . . .
C17 C 0.0862(5) 0.1949(3) 0.0376(2) 0.0593(10) Uani 1 1 d . . . . .
C18 C 0.1177(5) 0.2847(3) 0.0708(2) 0.0637(10) Uani 1 1 d . . . . .
H18 H 0.083383 0.344175 0.048186 0.076 Uiso 1 1 calc R U . . .
C19 C 0.2009(5) 0.2863(3) 0.1383(2) 0.0607(9) Uani 1 1 d . . . . .
H19 H 0.223673 0.347258 0.161487 0.073 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 C1 1.203(4) . ?
O2 C8 1.204(4) . ?
O3 N6 1.218(4) . ?
O4 N6 1.230(4) . ?
N1 C8 1.380(4) . ?
N1 C1 1.393(5) . ?
N1 C9 1.465(4) . ?
N2 N3 1.319(4) . ?
N2 C13 1.333(4) . ?
N3 N4 1.316(4) . ?
N3 C11 1.473(4) . ?
N4 N5 1.317(5) . ?
N5 C13 1.344(5) . ?
N6 C17 1.469(5) . ?
C1 C2 1.470(5) . ?
C2 C3 1.370(5) . ?
C2 C7 1.372(5) . ?
C3 C4 1.370(6) . ?
C4 C5 1.372(6) . ?
C5 C6 1.390(6) . ?
C6 C7 1.373(5) . ?
C7 C8 1.482(5) . ?
C9 C10 1.518(5) . ?
C10 C11 1.508(5) . ?
C11 C12 1.518(5) . ?
C13 C14 1.462(5) . ?
C14 C15 1.379(5) . ?
C14 C19 1.381(5) . ?
C15 C16 1.387(5) . ?
C16 C17 1.369(5) . ?
C17 C18 1.360(5) . ?
C18 C19 1.373(5) . ?

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
C8 N1 C1 111.4(3) . . ?
C8 N1 C9 125.2(3) . . ?
C1 N1 C9 122.8(3) . . ?
N3 N2 C13 101.6(3) . . ?
N4 N3 N2 114.3(3) . . ?
N4 N3 C11 122.6(3) . . ?
N2 N3 C11 123.1(3) . . ?
N3 N4 N5 105.8(3) . . ?
N4 N5 C13 106.4(3) . . ?
O3 N6 O4 122.8(4) . . ?
O3 N6 C17 118.6(4) . . ?
O4 N6 C17 118.6(4) . . ?
O1 C1 N1 124.4(4) . . ?
O1 C1 C2 129.3(4) . . ?
N1 C1 C2 106.3(3) . . ?
C3 C2 C7 121.8(4) . . ?
C3 C2 C1 130.3(4) . . ?
C7 C2 C1 107.9(3) . . ?
C2 C3 C4 117.7(4) . . ?
C3 C4 C5 120.8(4) . . ?
C4 C5 C6 122.0(4) . . ?
C7 C6 C5 116.4(4) . . ?
C2 C7 C6 121.4(4) . . ?
C2 C7 C8 108.4(3) . . ?
C6 C7 C8 130.2(4) . . ?
O2 C8 N1 125.3(4) . . ?
O2 C8 C7 128.9(4) . . ?
N1 C8 C7 105.8(3) . . ?
N1 C9 C10 112.6(3) . . ?
C11 C10 C9 115.1(3) . . ?
N3 C11 C10 109.4(3) . . ?
N3 C11 C12 110.0(3) . . ?
C10 C11 C12 112.5(3) . . ?
N2 C13 N5 111.9(4) . . ?
N2 C13 C14 124.3(3) . . ?
N5 C13 C14 123.8(3) . . ?
C15 C14 C19 119.7(4) . . ?
C15 C14 C13 120.6(3) . . ?
C19 C14 C13 119.7(3) . . ?
C14 C15 C16 120.5(3) . . ?
C17 C16 C15 117.9(4) . . ?
C18 C17 C16 122.6(4) . . ?
C18 C17 N6 118.9(4) . . ?
C16 C17 N6 118.4(4) . . ?
C17 C18 C19 119.1(4) . . ?
C18 C19 C14 120.1(4) . . ?

_refine_diff_density_max         0.106
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.030


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_RSHBuOACNO2
_database_code_depnum_ccdc_archive 'CCDC 2077948'
loop_
_audit_author_name
_audit_author_address
Elancheran
;Annamalai University
India
;
_audit_update_record             
;
2021-04-15 deposited with the CCDC.	2021-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            Organic
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 N5 O4'
_chemical_formula_sum            'C13 H15 N5 O4'
_chemical_formula_weight         305.30

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8987(6)
_cell_length_b                   10.2849(12)
_cell_length_c                   10.7179(14)
_cell_angle_alpha                116.598(13)
_cell_angle_beta                 101.905(9)
_cell_angle_gamma                90.188(8)
_cell_volume                     757.24(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5411
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      29.00

_exptl_crystal_description       Block
_exptl_crystal_colour            clear
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.630
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest XRD'
_diffrn_measurement_method       'Omega and Phi Scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            5389
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.019
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3417
_reflns_number_gt                1910
_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       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'
_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)+(0.1278P)²+0.1805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3417
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.2588
_refine_ls_wR_factor_gt          0.2033
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.2165(3) -0.2260(3) 0.1425(3) 0.0663(7) Uani 1 1 d . . . . .
O2 O 0.0316(3) -0.0690(3) 0.1639(4) 0.0853(9) Uani 1 1 d . . . . .
O3 O 1.1596(3) 0.7130(3) 0.4464(3) 0.0740(8) Uani 1 1 d . . . . .
O4 O 1.2283(4) 0.9372(4) 0.4820(4) 0.0960(10) Uani 1 1 d . . . . .
N1 N 0.6781(3) 0.4244(3) 0.1965(3) 0.0459(6) Uani 1 1 d . . . . .
N2 N 0.8356(3) 0.4690(3) 0.1939(3) 0.0445(6) Uani 1 1 d . . . . .
N3 N 0.9513(3) 0.3778(3) 0.1934(3) 0.0553(7) Uani 1 1 d . . . . .
N4 N 0.8691(3) 0.2663(3) 0.1945(3) 0.0562(7) Uani 1 1 d . . . . .
N5 N 0.1776(4) -0.1050(3) 0.1597(3) 0.0546(7) Uani 1 1 d . . . . .
C1 C 0.3146(4) 0.0013(3) 0.1732(3) 0.0429(7) Uani 1 1 d . . . . .
C2 C 0.4826(4) -0.0367(3) 0.1745(3) 0.0472(7) Uani 1 1 d . . . . .
H2 H 0.509264 -0.127051 0.168273 0.057 Uiso 1 1 calc R U . . .
C3 C 0.6092(4) 0.0623(3) 0.1850(3) 0.0459(7) Uani 1 1 d . . . . .
H3 H 0.722989 0.038843 0.186528 0.055 Uiso 1 1 calc R U . . .
C4 C 0.5687(4) 0.1971(3) 0.1935(3) 0.0396(6) Uani 1 1 d . . . . .
C5 C 0.3990(4) 0.2332(3) 0.1942(3) 0.0472(7) Uani 1 1 d . . . . .
H5 H 0.371863 0.324004 0.201810 0.057 Uiso 1 1 calc R U . . .
C6 C 0.2702(4) 0.1343(3) 0.1837(3) 0.0483(7) Uani 1 1 d . . . . .
H6 H 0.156481 0.157519 0.183704 0.058 Uiso 1 1 calc R U . . .
C7 C 0.7042(4) 0.2971(3) 0.1970(3) 0.0421(7) Uani 1 1 d . . . . .
C8 C 0.8766(4) 0.6057(3) 0.1879(3) 0.0461(7) Uani 1 1 d . . . . .
H8 H 0.995607 0.607398 0.174835 0.055 Uiso 1 1 calc R U . . .
C9 C 0.7561(5) 0.6075(4) 0.0601(4) 0.0647(9) Uani 1 1 d . . . . .
H9A H 0.762527 0.520915 -0.025195 0.097 Uiso 1 1 calc R U . . .
H9B H 0.790084 0.692346 0.051624 0.097 Uiso 1 1 calc R U . . .
H9C H 0.638972 0.610297 0.072397 0.097 Uiso 1 1 calc R U . . .
C10 C 0.8706(4) 0.7378(3) 0.3293(4) 0.0572(9) Uani 1 1 d . . . . .
H10A H 0.904283 0.825769 0.324211 0.069 Uiso 1 1 calc R U . . .
H10B H 0.751302 0.741233 0.339573 0.069 Uiso 1 1 calc R U . . .
C11 C 0.9842(5) 0.7400(4) 0.4610(4) 0.0675(10) Uani 1 1 d . . . . .
H11A H 0.986475 0.834588 0.542382 0.081 Uiso 1 1 calc R U . . .
H11B H 0.934744 0.666207 0.480059 0.081 Uiso 1 1 calc R U . . .
C12 C 1.2671(6) 0.8170(5) 0.4576(4) 0.0743(11) Uani 1 1 d . . . . .
C13 C 1.4408(5) 0.7619(6) 0.4360(5) 0.1021(17) Uani 1 1 d . . . . .
H13A H 1.462504 0.691456 0.471678 0.153 Uiso 1 1 calc R U . . .
H13B H 1.530948 0.842356 0.486995 0.153 Uiso 1 1 calc R U . . .
H13C H 1.439480 0.716697 0.335597 0.153 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 N5 1.224(3) . ?
O2 N5 1.216(4) . ?
O3 C12 1.309(5) . ?
O3 C11 1.440(4) . ?
O4 C12 1.199(5) . ?
N1 C7 1.329(4) . ?
N1 N2 1.334(3) . ?
N2 N3 1.311(3) . ?
N2 C8 1.474(4) . ?
N3 N4 1.322(4) . ?
N4 C7 1.344(4) . ?
N5 C1 1.474(4) . ?
C1 C6 1.374(4) . ?
C1 C2 1.383(4) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(4) . ?
C4 C7 1.465(4) . ?
C5 C6 1.387(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.505(4) . ?
C8 C10 1.527(4) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.498(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.509(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C12 O3 C11 119.9(3) . . ?
C7 N1 N2 101.6(2) . . ?
N3 N2 N1 113.7(2) . . ?
N3 N2 C8 122.5(2) . . ?
N1 N2 C8 123.8(2) . . ?
N2 N3 N4 106.2(2) . . ?
N3 N4 C7 106.2(2) . . ?
O2 N5 O1 123.4(3) . . ?
O2 N5 C1 118.5(3) . . ?
O1 N5 C1 118.1(3) . . ?
C6 C1 C2 122.5(3) . . ?
C6 C1 N5 118.6(3) . . ?
C2 C1 N5 118.8(3) . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 C7 119.4(3) . . ?
C5 C4 C7 121.0(3) . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
N1 C7 N4 112.2(2) . . ?
N1 C7 C4 124.6(2) . . ?
N4 C7 C4 123.2(3) . . ?
N2 C8 C9 109.8(2) . . ?
N2 C8 C10 110.3(2) . . ?
C9 C8 C10 113.0(3) . . ?
N2 C8 H8 107.9 . . ?
C9 C8 H8 107.9 . . ?
C10 C8 H8 107.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C8 115.5(3) . . ?
C11 C10 H10A 108.4 . . ?
C8 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C8 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
O3 C11 C10 112.3(3) . . ?
O3 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
O3 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
O4 C12 O3 123.2(4) . . ?
O4 C12 C13 126.7(5) . . ?
O3 C12 C13 110.0(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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 N1 N2 N3 -0.3(3) . . . . ?
C7 N1 N2 C8 178.1(2) . . . . ?
N1 N2 N3 N4 0.6(3) . . . . ?
C8 N2 N3 N4 -177.8(2) . . . . ?
N2 N3 N4 C7 -0.6(3) . . . . ?
O2 N5 C1 C6 -2.9(4) . . . . ?
O1 N5 C1 C6 176.1(3) . . . . ?
O2 N5 C1 C2 177.4(3) . . . . ?
O1 N5 C1 C2 -3.7(4) . . . . ?
C6 C1 C2 C3 -0.7(5) . . . . ?
N5 C1 C2 C3 179.0(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C2 C3 C4 C7 -176.8(3) . . . . ?
C3 C4 C5 C6 -1.3(4) . . . . ?
C7 C4 C5 C6 176.8(3) . . . . ?
C2 C1 C6 C5 0.7(5) . . . . ?
N5 C1 C6 C5 -179.0(3) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
N2 N1 C7 N4 -0.1(3) . . . . ?
N2 N1 C7 C4 -177.3(3) . . . . ?
N3 N4 C7 N1 0.5(3) . . . . ?
N3 N4 C7 C4 177.7(3) . . . . ?
C3 C4 C7 N1 175.8(3) . . . . ?
C5 C4 C7 N1 -2.2(4) . . . . ?
C3 C4 C7 N4 -1.0(4) . . . . ?
C5 C4 C7 N4 -179.1(3) . . . . ?
N3 N2 C8 C9 122.5(3) . . . . ?
N1 N2 C8 C9 -55.7(4) . . . . ?
N3 N2 C8 C10 -112.4(3) . . . . ?
N1 N2 C8 C10 69.4(3) . . . . ?
N2 C8 C10 C11 55.1(3) . . . . ?
C9 C8 C10 C11 178.4(3) . . . . ?
C12 O3 C11 C10 76.6(4) . . . . ?
C8 C10 C11 O3 49.4(4) . . . . ?
C11 O3 C12 O4 1.2(6) . . . . ?
C11 O3 C12 C13 -179.1(3) . . . . ?

_refine_diff_density_max         0.715
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.065

