# 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_EXWIFE
_database_code_depnum_ccdc_archive 'CCDC 2219199'
loop_
_audit_author_name
_audit_author_address
'Qi Zhou'
;Nangjing University of Science And Technology
China
;
_audit_update_record             
;
2022-11-11 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'2,9,9,10,10-pentanitro-2-azaadamantane-4,8-diyl dinitrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N8 O16'
_chemical_formula_sum            'C9 H8 N8 O16'
_chemical_formula_weight         484.23

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   10.1396(16)
_cell_length_b                   11.8452(18)
_cell_length_c                   14.454(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.443(2)
_cell_angle_gamma                90
_cell_volume                     1712.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2473
_cell_measurement_theta_min      2.6653
_cell_measurement_theta_max      25.7855

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.878
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.183
_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  0.975
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6550
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.665
_diffrn_reflns_theta_max         27.226
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1773
_reflns_number_gt                1479
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL
_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)+(0.0610P)²+1.3514P] 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         1773
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
C1 C 0.50070(15) 0.30943(13) 0.66370(10) 0.0258(4) Uani 1 1 d . . . . .
H1 H 0.501083 0.258283 0.610456 0.031 Uiso 1 1 calc R U . . .
C2 C 0.62717(15) 0.38265(13) 0.67979(11) 0.0263(4) Uani 1 1 d . . . . .
C3 C 0.62775(15) 0.45901(13) 0.76461(11) 0.0274(4) Uani 1 1 d . . . . .
H3 H 0.707732 0.506798 0.774000 0.033 Uiso 1 1 calc R U . . .
C4 C 0.500000 0.53269(19) 0.750000 0.0309(5) Uani 1 2 d S T P . .
H4A H 0.500082 0.580827 0.804299 0.037 Uiso 0.5 1 calc R U P . .
H4B H 0.499918 0.580826 0.695701 0.037 Uiso 0.5 1 calc R U P . .
C5 C 0.37809(15) 0.38705(14) 0.64740(11) 0.0277(4) Uani 1 1 d . . . . .
H5 H 0.383213 0.436677 0.593853 0.033 Uiso 1 1 calc R U . . .
N1 N 0.500000 0.24645(15) 0.750000 0.0280(4) Uani 1 2 d S T P . .
N2 N 0.500000 0.12938(17) 0.750000 0.0398(5) Uani 1 2 d S T P . .
N3 N 0.75417(14) 0.30957(13) 0.68727(10) 0.0340(4) Uani 1 1 d . . . . .
N4 N 0.63794(14) 0.45108(13) 0.59109(10) 0.0352(4) Uani 1 1 d . . . . .
N5 N 0.14811(16) 0.36441(18) 0.57392(12) 0.0482(5) Uani 1 1 d . . . . .
O1 O 0.48705(18) 0.08351(12) 0.67334(11) 0.0599(5) Uani 1 1 d . . . . .
O2 O 0.85834(13) 0.35848(14) 0.71102(12) 0.0586(5) Uani 1 1 d . . . . .
O3 O 0.74099(15) 0.21089(12) 0.66784(12) 0.0546(4) Uani 1 1 d . . . . .
O4 O 0.67648(15) 0.54734(12) 0.59979(10) 0.0526(4) Uani 1 1 d . . . . .
O5 O 0.60706(16) 0.40112(13) 0.51734(9) 0.0538(4) Uani 1 1 d . . . . .
O6 O 0.26763(11) 0.31078(11) 0.62430(9) 0.0375(3) Uani 1 1 d . . . . .
O7 O 0.15440(16) 0.46308(18) 0.55698(12) 0.0655(5) Uani 1 1 d . . . . .
O8 O 0.05914(17) 0.29959(18) 0.55648(14) 0.0812(6) 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
C1 N1 1.4544(17) . ?
C1 C5 1.533(2) . ?
C1 C2 1.534(2) . ?
C1 H1 0.9800 . ?
C2 C3 1.523(2) . ?
C2 N4 1.536(2) . ?
C2 N3 1.541(2) . ?
C3 C5 1.540(2) 2_656 ?
C3 C4 1.547(2) . ?
C3 H3 0.9800 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O6 1.4350(19) . ?
C5 H5 0.9800 . ?
N1 N2 1.387(3) . ?
N2 O1 1.2216(17) 2_656 ?
N2 O1 1.2217(17) . ?
N3 O2 1.204(2) . ?
N3 O3 1.204(2) . ?
N4 O4 1.205(2) . ?
N4 O5 1.215(2) . ?
N5 O8 1.180(2) . ?
N5 O7 1.198(3) . ?
N5 O6 1.454(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C5 108.75(12) . . ?
N1 C1 C2 106.36(11) . . ?
C5 C1 C2 108.72(13) . . ?
N1 C1 H1 111.0 . . ?
C5 C1 H1 111.0 . . ?
C2 C1 H1 111.0 . . ?
C3 C2 C1 110.52(13) . . ?
C3 C2 N4 111.54(13) . . ?
C1 C2 N4 110.13(12) . . ?
C3 C2 N3 112.61(12) . . ?
C1 C2 N3 111.18(13) . . ?
N4 C2 N3 100.49(12) . . ?
C2 C3 C5 109.91(13) . 2_656 ?
C2 C3 C4 109.42(11) . . ?
C5 C3 C4 106.27(12) 2_656 . ?
C2 C3 H3 110.4 . . ?
C5 C3 H3 110.4 2_656 . ?
C4 C3 H3 110.4 . . ?
C3 C4 C3 111.34(18) 2_656 . ?
C3 C4 H4A 109.4 2_656 . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 2_656 . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
O6 C5 C1 103.91(12) . . ?
O6 C5 C3 113.97(13) . 2_656 ?
C1 C5 C3 110.18(12) . 2_656 ?
O6 C5 H5 109.5 . . ?
C1 C5 H5 109.5 . . ?
C3 C5 H5 109.5 2_656 . ?
N2 N1 C1 120.86(8) . . ?
N2 N1 C1 120.86(8) . 2_656 ?
C1 N1 C1 118.28(17) . 2_656 ?
O1 N2 O1 127.2(2) 2_656 . ?
O1 N2 N1 116.42(11) 2_656 . ?
O1 N2 N1 116.41(11) . . ?
O2 N3 O3 126.29(16) . . ?
O2 N3 C2 115.69(15) . . ?
O3 N3 C2 118.00(14) . . ?
O4 N4 O5 125.81(16) . . ?
O4 N4 C2 118.59(15) . . ?
O5 N4 C2 115.60(14) . . ?
O8 N5 O7 131.0(2) . . ?
O8 N5 O6 111.6(2) . . ?
O7 N5 O6 117.44(16) . . ?
C5 O6 N5 113.34(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -57.36(15) . . . . ?
C5 C1 C2 C3 59.59(15) . . . . ?
N1 C1 C2 N4 178.94(12) . . . . ?
C5 C1 C2 N4 -64.10(16) . . . . ?
N1 C1 C2 N3 68.45(15) . . . . ?
C5 C1 C2 N3 -174.59(12) . . . . ?
C1 C2 C3 C5 59.15(15) . . . 2_656 ?
N4 C2 C3 C5 -177.98(12) . . . 2_656 ?
N3 C2 C3 C5 -65.86(16) . . . 2_656 ?
C1 C2 C3 C4 -57.18(16) . . . . ?
N4 C2 C3 C4 65.69(16) . . . . ?
N3 C2 C3 C4 177.81(12) . . . . ?
C2 C3 C4 C3 58.54(10) . . . 2_656 ?
C5 C3 C4 C3 -60.08(9) 2_656 . . 2_656 ?
N1 C1 C5 O6 -70.01(14) . . . . ?
C2 C1 C5 O6 174.58(12) . . . . ?
N1 C1 C5 C3 52.46(16) . . . 2_656 ?
C2 C1 C5 C3 -62.94(16) . . . 2_656 ?
C5 C1 N1 N2 122.34(9) . . . . ?
C2 C1 N1 N2 -120.74(9) . . . . ?
C5 C1 N1 C1 -57.66(9) . . . 2_656 ?
C2 C1 N1 C1 59.27(9) . . . 2_656 ?
C1 N1 N2 O1 172.88(12) . . . 2_656 ?
C1 N1 N2 O1 -7.12(12) 2_656 . . 2_656 ?
C1 N1 N2 O1 -7.12(12) . . . . ?
C1 N1 N2 O1 172.88(12) 2_656 . . . ?
C3 C2 N3 O2 -46.8(2) . . . . ?
C1 C2 N3 O2 -171.47(15) . . . . ?
N4 C2 N3 O2 71.98(18) . . . . ?
C3 C2 N3 O3 134.30(16) . . . . ?
C1 C2 N3 O3 9.7(2) . . . . ?
N4 C2 N3 O3 -106.90(16) . . . . ?
C3 C2 N4 O4 17.3(2) . . . . ?
C1 C2 N4 O4 140.35(16) . . . . ?
N3 C2 N4 O4 -102.31(17) . . . . ?
C3 C2 N4 O5 -163.38(14) . . . . ?
C1 C2 N4 O5 -40.29(19) . . . . ?
N3 C2 N4 O5 77.05(17) . . . . ?
C1 C5 O6 N5 -159.04(13) . . . . ?
C3 C5 O6 N5 81.02(16) 2_656 . . . ?
O8 N5 O6 C5 -179.63(17) . . . . ?
O7 N5 O6 C5 0.5(2) . . . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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 2219807'
loop_
_audit_author_name
_audit_author_address
'Qi Zhou'
;Nangjing University of Science And Technology
China
;
_audit_update_record             
;
2022-11-12 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'2-Nitro-2-azaadamantane-4,8,9,10-tetrayl tetranitrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 N6 O14'
_chemical_formula_sum            'C9 H10 N6 O14'
_chemical_formula_weight         426.23

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                   8.7329(11)
_cell_length_b                   11.6016(15)
_cell_length_c                   15.738(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1594.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3438
_cell_measurement_theta_min      2.6674
_cell_measurement_theta_max      25.0012

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.171
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.975
_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 D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12487
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.181
_diffrn_reflns_theta_max         27.237
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3266
_reflns_number_gt                2691
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_max     0.881
_reflns_Friedel_fraction_full    1.000

_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+0.0357P] 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 939 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3266
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0817
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C1 C 0.7524(3) 0.5012(2) 0.56326(16) 0.0293(6) Uani 1 1 d . . . . .
H1 H 0.796492 0.463162 0.513337 0.035 Uiso 1 1 calc R U . . .
C2 C 0.6302(3) 0.4261(2) 0.60376(17) 0.0289(6) Uani 1 1 d . . . . .
H2 H 0.676964 0.354473 0.624161 0.035 Uiso 1 1 calc R U . . .
C3 C 0.5540(3) 0.4882(2) 0.67808(16) 0.0294(6) Uani 1 1 d . . . . .
H3 H 0.473175 0.439932 0.702579 0.035 Uiso 1 1 calc R U . . .
C4 C 0.4862(3) 0.6009(2) 0.64465(17) 0.0304(6) Uani 1 1 d . . . . .
H4 H 0.409810 0.584931 0.600571 0.036 Uiso 1 1 calc R U . . .
C5 C 0.6124(3) 0.6781(2) 0.60947(16) 0.0312(6) Uani 1 1 d . . . . .
H5 H 0.569501 0.750715 0.588387 0.037 Uiso 1 1 calc R U . . .
C6 C 0.7330(3) 0.7010(2) 0.67751(17) 0.0319(6) Uani 1 1 d . . . . .
H6 H 0.686683 0.740725 0.726094 0.038 Uiso 1 1 calc R U . . .
C7 C 0.8058(3) 0.5872(2) 0.70638(17) 0.0314(6) Uani 1 1 d . . . . .
H7 H 0.884799 0.602268 0.749195 0.038 Uiso 1 1 calc R U . . .
C8 C 0.8771(3) 0.5290(2) 0.62872(16) 0.0315(6) Uani 1 1 d . . . . .
H8 H 0.955325 0.578938 0.603469 0.038 Uiso 1 1 calc R U . . .
C9 C 0.6781(3) 0.5126(2) 0.74466(17) 0.0332(6) Uani 1 1 d . . . . .
H9A H 0.720904 0.440394 0.764689 0.040 Uiso 1 1 calc R U . . .
H9B H 0.633071 0.552173 0.792861 0.040 Uiso 1 1 calc R U . . .
N1 N 0.6802(3) 0.61145(19) 0.53936(13) 0.0317(5) Uani 1 1 d . . . . .
N2 N 0.7450(3) 0.6726(2) 0.47376(15) 0.0425(6) Uani 1 1 d . . . . .
N3 N 0.4469(3) 0.2924(2) 0.54450(17) 0.0414(6) Uani 1 1 d . . . . .
N4 N 0.2648(3) 0.6448(2) 0.72913(16) 0.0385(6) Uani 1 1 d . . . . .
N5 N 0.8296(4) 0.8887(2) 0.63938(18) 0.0560(8) Uani 1 1 d . . . . .
N6 N 1.0707(3) 0.3842(2) 0.61213(19) 0.0457(6) Uani 1 1 d . . . . .
O1 O 0.7035(3) 0.77202(19) 0.46361(15) 0.0611(7) Uani 1 1 d . . . . .
O2 O 0.8351(3) 0.6214(2) 0.42792(14) 0.0612(7) Uani 1 1 d . . . . .
O3 O 0.5226(2) 0.39966(15) 0.53571(11) 0.0368(5) Uani 1 1 d . . . . .
O4 O 0.4694(3) 0.23772(18) 0.60760(16) 0.0601(7) Uani 1 1 d . . . . .
O5 O 0.3681(3) 0.27177(19) 0.48437(15) 0.0575(6) Uani 1 1 d . . . . .
O6 O 0.4189(2) 0.66972(16) 0.71213(12) 0.0357(5) Uani 1 1 d . . . . .
O7 O 0.2080(2) 0.56443(18) 0.69304(15) 0.0488(6) Uani 1 1 d . . . . .
O8 O 0.2092(3) 0.7089(2) 0.77900(18) 0.0690(8) Uani 1 1 d . . . . .
O9 O 0.8589(2) 0.76900(15) 0.64344(13) 0.0418(5) Uani 1 1 d . . . . .
O10 O 0.9397(4) 0.9407(2) 0.6161(2) 0.0990(11) Uani 1 1 d . . . . .
O11 O 0.7048(3) 0.92229(18) 0.65892(17) 0.0646(7) Uani 1 1 d . . . . .
O12 O 0.9462(2) 0.42413(15) 0.66087(12) 0.0381(5) Uani 1 1 d . . . . .
O13 O 1.0958(3) 0.4291(2) 0.54528(16) 0.0594(7) Uani 1 1 d . . . . .
O14 O 1.1367(3) 0.3065(2) 0.64630(17) 0.0682(7) 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
C1 N1 1.475(3) . ?
C1 C2 1.518(4) . ?
C1 C8 1.533(4) . ?
C1 H1 0.9800 . ?
C2 O3 1.457(3) . ?
C2 C3 1.526(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.528(4) . ?
C3 C9 1.534(4) . ?
C3 H3 0.9800 . ?
C4 O6 1.453(3) . ?
C4 C5 1.524(4) . ?
C4 H4 0.9800 . ?
C5 N1 1.471(3) . ?
C5 C6 1.525(4) . ?
C5 H5 0.9800 . ?
C6 O9 1.455(3) . ?
C6 C7 1.534(4) . ?
C6 H6 0.9800 . ?
C7 C8 1.529(4) . ?
C7 C9 1.535(4) . ?
C7 H7 0.9800 . ?
C8 O12 1.450(3) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N1 N2 1.375(3) . ?
N2 O1 1.220(3) . ?
N2 O2 1.221(3) . ?
N3 O5 1.194(3) . ?
N3 O4 1.194(3) . ?
N3 O3 1.416(3) . ?
N4 O8 1.185(3) . ?
N4 O7 1.199(3) . ?
N4 O6 1.402(3) . ?
N5 O10 1.193(4) . ?
N5 O11 1.198(4) . ?
N5 O9 1.413(3) . ?
N6 O13 1.194(3) . ?
N6 O14 1.197(3) . ?
N6 O12 1.409(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 107.7(2) . . ?
N1 C1 C8 107.0(2) . . ?
C2 C1 C8 109.7(2) . . ?
N1 C1 H1 110.8 . . ?
C2 C1 H1 110.8 . . ?
C8 C1 H1 110.8 . . ?
O3 C2 C1 105.4(2) . . ?
O3 C2 C3 112.4(2) . . ?
C1 C2 C3 110.9(2) . . ?
O3 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
C2 C3 C4 108.0(2) . . ?
C2 C3 C9 107.6(2) . . ?
C4 C3 C9 110.6(2) . . ?
C2 C3 H3 110.2 . . ?
C4 C3 H3 110.2 . . ?
C9 C3 H3 110.2 . . ?
O6 C4 C5 103.58(19) . . ?
O6 C4 C3 112.0(2) . . ?
C5 C4 C3 110.3(2) . . ?
O6 C4 H4 110.2 . . ?
C5 C4 H4 110.2 . . ?
C3 C4 H4 110.2 . . ?
N1 C5 C4 104.7(2) . . ?
N1 C5 C6 109.9(2) . . ?
C4 C5 C6 110.3(2) . . ?
N1 C5 H5 110.6 . . ?
C4 C5 H5 110.6 . . ?
C6 C5 H5 110.6 . . ?
O9 C6 C5 110.9(2) . . ?
O9 C6 C7 105.2(2) . . ?
C5 C6 C7 110.1(2) . . ?
O9 C6 H6 110.2 . . ?
C5 C6 H6 110.2 . . ?
C7 C6 H6 110.2 . . ?
C8 C7 C6 108.2(2) . . ?
C8 C7 C9 111.1(2) . . ?
C6 C7 C9 107.5(2) . . ?
C8 C7 H7 110.0 . . ?
C6 C7 H7 110.0 . . ?
C9 C7 H7 110.0 . . ?
O12 C8 C7 105.1(2) . . ?
O12 C8 C1 110.7(2) . . ?
C7 C8 C1 109.9(2) . . ?
O12 C8 H8 110.3 . . ?
C7 C8 H8 110.3 . . ?
C1 C8 H8 110.3 . . ?
C3 C9 C7 110.4(2) . . ?
C3 C9 H9A 109.6 . . ?
C7 C9 H9A 109.6 . . ?
C3 C9 H9B 109.6 . . ?
C7 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N2 N1 C5 117.2(2) . . ?
N2 N1 C1 117.6(2) . . ?
C5 N1 C1 115.88(19) . . ?
O1 N2 O2 125.0(3) . . ?
O1 N2 N1 117.6(3) . . ?
O2 N2 N1 117.3(3) . . ?
O5 N3 O4 130.3(3) . . ?
O5 N3 O3 111.6(2) . . ?
O4 N3 O3 118.1(2) . . ?
O8 N4 O7 129.2(3) . . ?
O8 N4 O6 112.9(2) . . ?
O7 N4 O6 117.8(2) . . ?
O10 N5 O11 130.3(3) . . ?
O10 N5 O9 111.5(3) . . ?
O11 N5 O9 118.2(3) . . ?
O13 N6 O14 129.4(3) . . ?
O13 N6 O12 118.5(3) . . ?
O14 N6 O12 112.0(3) . . ?
N3 O3 C2 114.5(2) . . ?
N4 O6 C4 114.5(2) . . ?
N5 O9 C6 114.4(2) . . ?
N6 O12 C8 114.1(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
N1 C1 C2 O3 66.8(2) . . . . ?
C8 C1 C2 O3 -177.0(2) . . . . ?
N1 C1 C2 C3 -55.1(3) . . . . ?
C8 C1 C2 C3 61.1(3) . . . . ?
O3 C2 C3 C4 -59.9(3) . . . . ?
C1 C2 C3 C4 57.8(3) . . . . ?
O3 C2 C3 C9 -179.3(2) . . . . ?
C1 C2 C3 C9 -61.6(3) . . . . ?
C2 C3 C4 O6 -176.5(2) . . . . ?
C9 C3 C4 O6 -59.0(3) . . . . ?
C2 C3 C4 C5 -61.7(3) . . . . ?
C9 C3 C4 C5 55.8(3) . . . . ?
O6 C4 C5 N1 -178.62(19) . . . . ?
C3 C4 C5 N1 61.3(2) . . . . ?
O6 C4 C5 C6 63.2(3) . . . . ?
C3 C4 C5 C6 -56.9(3) . . . . ?
N1 C5 C6 O9 61.7(3) . . . . ?
C4 C5 C6 O9 176.6(2) . . . . ?
N1 C5 C6 C7 -54.4(3) . . . . ?
C4 C5 C6 C7 60.6(3) . . . . ?
O9 C6 C7 C8 -61.0(3) . . . . ?
C5 C6 C7 C8 58.6(3) . . . . ?
O9 C6 C7 C9 178.9(2) . . . . ?
C5 C6 C7 C9 -61.5(3) . . . . ?
C6 C7 C8 O12 178.73(19) . . . . ?
C9 C7 C8 O12 -63.5(3) . . . . ?
C6 C7 C8 C1 -62.0(3) . . . . ?
C9 C7 C8 C1 55.7(3) . . . . ?
N1 C1 C8 O12 175.5(2) . . . . ?
C2 C1 C8 O12 58.9(3) . . . . ?
N1 C1 C8 C7 59.7(3) . . . . ?
C2 C1 C8 C7 -56.9(3) . . . . ?
C2 C3 C9 C7 59.2(3) . . . . ?
C4 C3 C9 C7 -58.5(3) . . . . ?
C8 C7 C9 C3 -57.8(3) . . . . ?
C6 C7 C9 C3 60.4(3) . . . . ?
C4 C5 N1 N2 151.8(2) . . . . ?
C6 C5 N1 N2 -89.8(3) . . . . ?
C4 C5 N1 C1 -62.3(3) . . . . ?
C6 C5 N1 C1 56.1(3) . . . . ?
C2 C1 N1 N2 -154.2(2) . . . . ?
C8 C1 N1 N2 87.8(3) . . . . ?
C2 C1 N1 C5 60.0(3) . . . . ?
C8 C1 N1 C5 -58.0(3) . . . . ?
C5 N1 N2 O1 -22.0(4) . . . . ?
C1 N1 N2 O1 -167.3(3) . . . . ?
C5 N1 N2 O2 161.1(2) . . . . ?
C1 N1 N2 O2 15.7(4) . . . . ?
O5 N3 O3 C2 -175.4(2) . . . . ?
O4 N3 O3 C2 4.6(3) . . . . ?
C1 C2 O3 N3 150.5(2) . . . . ?
C3 C2 O3 N3 -88.6(2) . . . . ?
O8 N4 O6 C4 -173.7(2) . . . . ?
O7 N4 O6 C4 6.4(3) . . . . ?
C5 C4 O6 N4 152.8(2) . . . . ?
C3 C4 O6 N4 -88.3(3) . . . . ?
O10 N5 O9 C6 175.6(3) . . . . ?
O11 N5 O9 C6 -4.2(4) . . . . ?
C5 C6 O9 N5 81.0(3) . . . . ?
C7 C6 O9 N5 -159.9(2) . . . . ?
O13 N6 O12 C8 -9.2(3) . . . . ?
O14 N6 O12 C8 171.0(2) . . . . ?
C7 C8 O12 N6 -153.4(2) . . . . ?
C1 C8 O12 N6 87.9(2) . . . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038

