# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

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

data_fsba17_0m
_database_code_depnum_ccdc_archive 'CCDC 2246333'
loop_
_audit_author_name
_audit_author_address
'Shangbiao Feng' 'North University of China'
_audit_update_record             
;
2023-03-05 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H5 N8'
_chemical_formula_weight         225.21

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   5.4523(16)
_cell_length_b                   12.972(4)
_cell_length_c                   14.974(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1059.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1435
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      21.78

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6680
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.077
_diffrn_reflns_theta_max         27.786
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2476
_reflns_number_gt                1913
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.997

_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0500P)²] 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_abs_structure_details 
;
 Flack x determined using 592 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2476
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
N1 N 0.3378(4) 0.71313(15) 0.33825(12) 0.0363(5) Uani 1 1 d . . . . .
N2 N 0.6894(4) 0.93975(16) 0.38195(14) 0.0458(6) Uani 1 1 d . . . . .
N3 N 0.8230(4) 0.86872(16) 0.41900(15) 0.0465(6) Uani 1 1 d . . . . .
N4 N 0.7007(4) 0.77811(14) 0.40507(13) 0.0346(5) Uani 1 1 d . . . . .
N5 N 0.7817(4) 0.68839(14) 0.43756(12) 0.0359(5) Uani 1 1 d . . . . .
N6 N 0.1789(5) 1.00828(17) 0.25845(16) 0.0565(6) Uani 1 1 d . . . . .
N7 N 0.7556(6) 0.4337(2) 0.48210(17) 0.0661(8) Uani 1 1 d . . . . .
N8 N 0.2390(7) 0.3072(2) 0.3464(2) 0.0947(11) Uani 1 1 d . . . . .
C1 C 0.3139(6) 0.95827(19) 0.29745(16) 0.0415(6) Uani 1 1 d . . . . .
C2 C 0.4849(5) 0.89739(18) 0.34475(14) 0.0360(6) Uani 1 1 d . . . . .
C3 C 0.4872(5) 0.79209(18) 0.35899(14) 0.0325(5) Uani 1 1 d . . . . .
C4 C 0.4101(4) 0.62217(18) 0.36772(16) 0.0358(6) Uani 1 1 d . . . . .
C5 C 0.6367(5) 0.61193(17) 0.41890(15) 0.0345(6) Uani 1 1 d . . . . .
C7 C 0.7074(6) 0.5132(2) 0.45441(16) 0.0435(6) Uani 1 1 d . . . . .
C8 C -0.1438(7) 0.2022(2) 0.3867(2) 0.0658(9) Uani 1 1 d . . . . .
H8A H -0.166336 0.203637 0.450289 0.099 Uiso 1 1 calc R U . . .
H8B H -0.124592 0.132138 0.367265 0.099 Uiso 1 1 calc R U . . .
H8C H -0.284327 0.232058 0.358047 0.099 Uiso 1 1 calc R U . . .
C9 C 0.0711(7) 0.2600(2) 0.3637(2) 0.0614(9) Uani 1 1 d . . . . .
N9 N 0.2773(4) 0.53903(16) 0.35077(14) 0.0481(6) Uani 1 1 d . . . . .
H9A H 0.143826 0.544226 0.320524 0.058 Uiso 1 1 calc R U . . .
H9B H 0.324607 0.479805 0.370002 0.058 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
N1 C4 1.320(3) . ?
N1 C3 1.345(3) . ?
N2 N3 1.299(3) . ?
N2 C2 1.362(3) . ?
N3 N4 1.367(3) . ?
N4 N5 1.336(2) . ?
N4 C3 1.365(3) . ?
N5 C5 1.299(3) . ?
N6 C1 1.142(3) . ?
N7 C7 1.142(3) . ?
N8 C9 1.131(4) . ?
C1 C2 1.412(4) . ?
C2 C3 1.383(3) . ?
C4 N9 1.323(3) . ?
C4 C5 1.460(3) . ?
C5 C7 1.440(3) . ?
C8 C9 1.433(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?

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
C4 N1 C3 115.0(2) . . ?
N3 N2 C2 110.3(2) . . ?
N2 N3 N4 105.73(19) . . ?
N5 N4 C3 125.53(19) . . ?
N5 N4 N3 122.15(19) . . ?
C3 N4 N3 112.26(19) . . ?
C5 N5 N4 112.70(19) . . ?
N6 C1 C2 178.8(3) . . ?
N2 C2 C3 109.1(2) . . ?
N2 C2 C1 121.3(2) . . ?
C3 C2 C1 129.5(2) . . ?
N1 C3 N4 122.1(2) . . ?
N1 C3 C2 135.3(2) . . ?
N4 C3 C2 102.5(2) . . ?
N1 C4 N9 120.1(2) . . ?
N1 C4 C5 120.6(2) . . ?
N9 C4 C5 119.3(2) . . ?
N5 C5 C7 115.9(2) . . ?
N5 C5 C4 124.0(2) . . ?
C7 C5 C4 120.1(2) . . ?
N7 C7 C5 177.7(3) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N8 C9 C8 178.7(4) . . ?
C4 N9 H9A 120.0 . . ?
C4 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?

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
C2 N2 N3 N4 0.1(3) . . . . ?
N2 N3 N4 N5 -177.4(2) . . . . ?
N2 N3 N4 C3 -0.2(3) . . . . ?
C3 N4 N5 C5 1.6(3) . . . . ?
N3 N4 N5 C5 178.4(2) . . . . ?
N3 N2 C2 C3 0.1(3) . . . . ?
N3 N2 C2 C1 -177.7(2) . . . . ?
C4 N1 C3 N4 1.7(3) . . . . ?
C4 N1 C3 C2 -178.4(3) . . . . ?
N5 N4 C3 N1 -2.8(4) . . . . ?
N3 N4 C3 N1 -179.8(2) . . . . ?
N5 N4 C3 C2 177.3(2) . . . . ?
N3 N4 C3 C2 0.2(3) . . . . ?
N2 C2 C3 N1 179.9(2) . . . . ?
C1 C2 C3 N1 -2.6(5) . . . . ?
N2 C2 C3 N4 -0.2(3) . . . . ?
C1 C2 C3 N4 177.4(2) . . . . ?
C3 N1 C4 N9 -179.7(2) . . . . ?
C3 N1 C4 C5 0.1(3) . . . . ?
N4 N5 C5 C7 -177.9(2) . . . . ?
N4 N5 C5 C4 0.2(3) . . . . ?
N1 C4 C5 N5 -1.1(4) . . . . ?
N9 C4 C5 N5 178.7(2) . . . . ?
N1 C4 C5 C7 177.0(2) . . . . ?
N9 C4 C5 C7 -3.2(3) . . . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_A61_0m
_database_code_depnum_ccdc_archive 'CCDC 2246334'
loop_
_audit_author_name
_audit_author_address
'Shangbiao Feng'
;North University of China
China
;
_audit_update_record             
;
2023-03-05 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H9 N11 O3'
_chemical_formula_weight         283.24

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   5.6133(12)
_cell_length_b                   13.359(3)
_cell_length_c                   16.245(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1218.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    356
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      24.75

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7107
_diffrn_reflns_av_unetI/netI     0.0910
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.508
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2474
_reflns_number_gt                1696
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.994

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0373P)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_abs_structure_details 
;
 Flack x determined using 477 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2474
_refine_ls_number_parameters     199
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.0894
_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
O1 O -0.0135(6) 0.2188(2) 0.6775(2) 0.0321(9) Uani 1 1 d D . . . .
H1WA H -0.074(9) 0.172(3) 0.707(3) 0.048 Uiso 1 1 d D U . . .
H1WB H 0.052(9) 0.266(3) 0.705(3) 0.048 Uiso 1 1 d D U . . .
O2 O 0.8105(6) 0.3542(2) 0.4356(2) 0.0326(8) Uani 1 1 d D . . . .
H2WB H 0.929(7) 0.314(3) 0.435(3) 0.049 Uiso 1 1 d D U . . .
H2WA H 0.710(8) 0.333(3) 0.401(3) 0.049 Uiso 1 1 d D U . . .
O3 O 0.6310(6) 0.3052(2) 0.5895(2) 0.0305(8) Uani 1 1 d D . . . .
H3WA H 0.690(10) 0.326(3) 0.545(2) 0.046 Uiso 1 1 d D U . . .
H3WB H 0.748(7) 0.281(3) 0.617(3) 0.046 Uiso 1 1 d D U . . .
N1 N 0.2201(7) 0.5613(3) 0.7400(2) 0.0263(9) Uani 1 1 d . . . . .
N2 N 0.1144(7) 0.4746(3) 0.7633(2) 0.0282(10) Uani 1 1 d . . . . .
N3 N 0.2164(7) 0.3983(3) 0.7270(2) 0.0282(10) Uani 1 1 d . . . . .
N4 N 0.3910(7) 0.4356(3) 0.6791(2) 0.0276(9) Uani 1 1 d . . . . .
H4 H 0.4875 0.4005 0.6476 0.033 Uiso 1 1 calc R U . . .
N5 N 0.7568(7) 0.5602(3) 0.6102(2) 0.0303(10) Uani 1 1 d . . . . .
N6 N 0.8839(7) 0.6300(3) 0.5742(2) 0.0296(10) Uani 1 1 d . . . . .
N7 N 0.7595(7) 0.7168(2) 0.5870(2) 0.0251(9) Uani 1 1 d . . . . .
N8 N 0.8363(7) 0.8042(3) 0.5556(2) 0.0257(9) Uani 1 1 d . . . . .
N9 N 0.4021(7) 0.7783(3) 0.6480(2) 0.0236(9) Uani 1 1 d . . . . .
N10 N 0.8045(8) 1.0527(3) 0.5158(3) 0.0378(11) Uani 1 1 d . . . . .
N11 N 0.3336(7) 0.9480(2) 0.6312(2) 0.0288(9) Uani 1 1 d . . . . .
H11A H 0.2020 0.9433 0.6604 0.035 Uiso 1 1 calc R U . . .
H11B H 0.3776 1.0062 0.6109 0.035 Uiso 1 1 calc R U . . .
C1 C 0.3920(8) 0.5358(3) 0.6877(3) 0.0235(10) Uani 1 1 d . . . . .
C2 C 0.5576(8) 0.6000(3) 0.6455(3) 0.0238(10) Uani 1 1 d . . . . .
C3 C 0.5524(8) 0.7026(3) 0.6312(3) 0.0234(10) Uani 1 1 d . . . . .
C4 C 0.4661(8) 0.8670(3) 0.6177(3) 0.0239(10) Uani 1 1 d . . . . .
C5 C 0.6872(9) 0.8771(3) 0.5709(3) 0.0239(10) Uani 1 1 d . . . . .
C6 C 0.7582(9) 0.9744(4) 0.5391(3) 0.0271(11) 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
O1 H1WA 0.86(2) . ?
O1 H1WB 0.85(2) . ?
O2 H2WB 0.86(2) . ?
O2 H2WA 0.85(2) . ?
O3 H3WA 0.84(2) . ?
O3 H3WB 0.85(2) . ?
N1 C1 1.330(6) . ?
N1 N2 1.355(5) . ?
N2 N3 1.309(5) . ?
N3 N4 1.347(5) . ?
N4 C1 1.346(5) . ?
N4 H4 0.8800 . ?
N5 N6 1.311(5) . ?
N5 C2 1.365(6) . ?
N6 N7 1.370(5) . ?
N7 N8 1.345(5) . ?
N7 C3 1.379(5) . ?
N8 C5 1.308(5) . ?
N9 C4 1.332(5) . ?
N9 C3 1.345(5) . ?
N10 C6 1.142(5) . ?
N11 C4 1.331(5) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
C1 C2 1.439(6) . ?
C2 C3 1.391(6) . ?
C4 C5 1.462(6) . ?
C5 C6 1.455(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1WA O1 H1WB 114(5) . . ?
H2WB O2 H2WA 107(5) . . ?
H3WA O3 H3WB 105(5) . . ?
C1 N1 N2 106.0(3) . . ?
N3 N2 N1 110.4(4) . . ?
N2 N3 N4 106.9(3) . . ?
C1 N4 N3 108.1(4) . . ?
C1 N4 H4 126.0 . . ?
N3 N4 H4 125.9 . . ?
N6 N5 C2 110.9(4) . . ?
N5 N6 N7 104.9(4) . . ?
N8 N7 N6 120.9(4) . . ?
N8 N7 C3 125.9(4) . . ?
N6 N7 C3 113.1(3) . . ?
C5 N8 N7 111.6(4) . . ?
C4 N9 C3 115.1(4) . . ?
C4 N11 H11A 120.0 . . ?
C4 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
N1 C1 N4 108.6(4) . . ?
N1 C1 C2 128.3(4) . . ?
N4 C1 C2 123.1(4) . . ?
N5 C2 C3 109.3(4) . . ?
N5 C2 C1 119.9(4) . . ?
C3 C2 C1 130.9(4) . . ?
N9 C3 N7 122.1(4) . . ?
N9 C3 C2 136.0(4) . . ?
N7 C3 C2 101.8(4) . . ?
N11 C4 N9 120.8(4) . . ?
N11 C4 C5 119.0(4) . . ?
N9 C4 C5 120.2(4) . . ?
N8 C5 C6 115.0(4) . . ?
N8 C5 C4 125.0(4) . . ?
C6 C5 C4 120.0(4) . . ?
N10 C6 C5 176.7(5) . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.057

