# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_67YU
_audit_block_doi                 10.5517/ccdc.csd.cc27h7gg
_database_code_depnum_ccdc_archive 'CCDC 2070225'
loop_
_audit_author_name
_audit_author_address
'Rong-bin Cai'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2021-03-14 deposited with the CCDC.	2022-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(1'r,3'r,5'r,7'r)-4',8',9',10'-tetrabenzyl-4',8',9',10'-tetraazadispiro[[1,3]dioxolane-2,2'-adamantane-6',2''-[1,3]dioxolane]
_chemical_name_common            
2,4,6,8-tetrabenzyl-2,4,6,8-tetraazaadamantane
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H40 N4 O4'
_chemical_formula_sum            'C38 H40 N4 O4'
_chemical_formula_weight         616.74

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                   30.685(13)
_cell_length_b                   14.167(6)
_cell_length_c                   17.295(7)
_cell_angle_alpha                90
_cell_angle_beta                 119.995(5)
_cell_angle_gamma                90
_cell_volume                     6511(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5292
_cell_measurement_theta_min      2.3547
_cell_measurement_theta_max      23.0079

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             2624
_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    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.988
_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            25069
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.533
_diffrn_reflns_theta_max         27.316
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6749
_reflns_number_gt                4172
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0696P)²+4.7498P] 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         6749
_refine_ls_number_parameters     415
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1635
_refine_ls_wR_factor_gt          0.1396
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.069
_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 0.20387(7) 0.98065(16) 0.30105(13) 0.0431(5) Uani 1 1 d . . . . .
H1 H 0.239340 0.999393 0.330522 0.052 Uiso 1 1 calc R U . . .
C2 C 0.12147(7) 1.02851(15) 0.27125(13) 0.0409(5) Uani 1 1 d . . . . .
H2 H 0.102503 1.078699 0.280316 0.049 Uiso 1 1 calc R U . . .
C3 C 0.12869(8) 0.93944(16) 0.15975(14) 0.0469(5) Uani 1 1 d . . . . .
H3 H 0.114345 0.930178 0.095381 0.056 Uiso 1 1 calc R U . . .
C4 C 0.14660(7) 0.86182(16) 0.29606(13) 0.0421(5) Uani 1 1 d . . . . .
H4 H 0.144360 0.801773 0.321978 0.050 Uiso 1 1 calc R U . . .
C5 C 0.11717(7) 0.93785(15) 0.31391(13) 0.0404(5) Uani 1 1 d . . . . .
C6 C 0.18397(8) 0.96835(17) 0.20063(14) 0.0483(5) Uani 1 1 d . . . . .
C7 C 0.18431(9) 1.15096(16) 0.30525(15) 0.0516(6) Uani 1 1 d . . . . .
H7A H 0.163809 1.167230 0.242612 0.062 Uiso 1 1 calc R U . . .
H7B H 0.219339 1.158301 0.321735 0.062 Uiso 1 1 calc R U . . .
C8 C 0.17242(8) 1.21759(16) 0.36025(15) 0.0495(6) Uani 1 1 d . . . . .
C9 C 0.18936(11) 1.2013(2) 0.44911(18) 0.0720(8) Uani 1 1 d . . . . .
H9 H 0.207087 1.146069 0.475071 0.086 Uiso 1 1 calc R U . . .
C10 C 0.18093(12) 1.2640(2) 0.5008(2) 0.0795(8) Uani 1 1 d . . . . .
H10 H 0.192786 1.250788 0.560734 0.095 Uiso 1 1 calc R U . . .
C11 C 0.15534(12) 1.3450(2) 0.4645(2) 0.0813(9) Uani 1 1 d . . . . .
H11 H 0.150167 1.388422 0.499464 0.098 Uiso 1 1 calc R U . . .
C12 C 0.13728(15) 1.3622(2) 0.3760(2) 0.0975(11) Uani 1 1 d . . . . .
H12 H 0.119245 1.417188 0.350285 0.117 Uiso 1 1 calc R U . . .
C13 C 0.14568(12) 1.2981(2) 0.3243(2) 0.0782(8) Uani 1 1 d . . . . .
H13 H 0.132804 1.310359 0.263868 0.094 Uiso 1 1 calc R U . . .
C14 C 0.23214(8) 0.87745(18) 0.43088(13) 0.0501(6) Uani 1 1 d . . . . .
H14A H 0.221141 0.822842 0.450439 0.060 Uiso 1 1 calc R U . . .
H14B H 0.228901 0.932525 0.460954 0.060 Uiso 1 1 calc R U . . .
C15 C 0.28680(8) 0.86495(15) 0.45692(13) 0.0440(5) Uani 1 1 d . . . . .
C16 C 0.30098(9) 0.8257(2) 0.40005(16) 0.0650(7) Uani 1 1 d . . . . .
H16 H 0.276418 0.804930 0.343954 0.078 Uiso 1 1 calc R U . . .
C17 C 0.35114(10) 0.8168(2) 0.42504(18) 0.0788(9) Uani 1 1 d . . . . .
H17 H 0.360032 0.790545 0.385559 0.095 Uiso 1 1 calc R U . . .
C18 C 0.38775(9) 0.8462(2) 0.50730(19) 0.0735(8) Uani 1 1 d . . . . .
H18 H 0.421500 0.841185 0.523652 0.088 Uiso 1 1 calc R U . . .
C19 C 0.37427(9) 0.8833(2) 0.56570(19) 0.0721(8) Uani 1 1 d . . . . .
H19 H 0.398982 0.901998 0.622473 0.087 Uiso 1 1 calc R U . . .
C20 C 0.32407(9) 0.89283(17) 0.54026(16) 0.0582(6) Uani 1 1 d . . . . .
H20 H 0.315314 0.918520 0.580106 0.070 Uiso 1 1 calc R U . . .
C21 C 0.13355(9) 0.76409(18) 0.16886(16) 0.0593(6) Uani 1 1 d . . . . .
H21A H 0.168986 0.749385 0.206221 0.071 Uiso 1 1 calc R U . . .
H21B H 0.126852 0.771981 0.108163 0.071 Uiso 1 1 calc R U . . .
C22 C 0.10272(9) 0.68270(17) 0.17171(15) 0.0578(6) Uani 1 1 d . . . . .
C23 C 0.05909(10) 0.6955(2) 0.17465(17) 0.0672(7) Uani 1 1 d . . . . .
H23 H 0.048693 0.756359 0.177594 0.081 Uiso 1 1 calc R U . . .
C24 C 0.03050(12) 0.6196(2) 0.1733(2) 0.0871(9) Uani 1 1 d . . . . .
H24 H 0.001402 0.629541 0.176246 0.105 Uiso 1 1 calc R U . . .
C25 C 0.0450(2) 0.5303(3) 0.1677(3) 0.1143(14) Uani 1 1 d . . . . .
H25 H 0.025629 0.479129 0.166358 0.137 Uiso 1 1 calc R U . . .
C26 C 0.0876(2) 0.5159(3) 0.1640(3) 0.1237(15) Uani 1 1 d . . . . .
H26 H 0.097355 0.454801 0.159820 0.148 Uiso 1 1 calc R U . . .
C27 C 0.11657(14) 0.5912(2) 0.1663(2) 0.0937(10) Uani 1 1 d . . . . .
H27 H 0.145872 0.580372 0.164283 0.112 Uiso 1 1 calc R U . . .
C28 C 0.04826(8) 1.01512(17) 0.11539(15) 0.0522(6) Uani 1 1 d . . . . .
H28A H 0.034138 0.967552 0.136858 0.063 Uiso 1 1 calc R U . . .
H28B H 0.040776 0.996848 0.055932 0.063 Uiso 1 1 calc R U . . .
C29 C 0.02373(8) 1.10828(17) 0.11029(14) 0.0486(5) Uani 1 1 d . . . . .
C30 C -0.01170(12) 1.1177(2) 0.1353(2) 0.0896(10) Uani 1 1 d . U . . .
H30 H -0.019574 1.066340 0.159516 0.107 Uiso 1 1 calc R U . . .
C31 C -0.03611(13) 1.2029(3) 0.1249(3) 0.1027(10) Uani 1 1 d . U . . .
H31 H -0.060512 1.207909 0.141635 0.123 Uiso 1 1 calc R U . . .
C32 C -0.02487(12) 1.2791(2) 0.0908(2) 0.0904(10) Uani 1 1 d . . . . .
H32 H -0.041272 1.336230 0.084358 0.108 Uiso 1 1 calc R U . . .
C33 C 0.01025(12) 1.2713(2) 0.0663(2) 0.0831(9) Uani 1 1 d . . . . .
H33 H 0.018112 1.323227 0.042653 0.100 Uiso 1 1 calc R U . . .
C34 C 0.03465(10) 1.1866(2) 0.07592(19) 0.0696(7) Uani 1 1 d . . . . .
H34 H 0.058942 1.182343 0.058910 0.083 Uiso 1 1 calc R U . . .
C35 C 0.06339(9) 0.86668(18) 0.35066(16) 0.0585(6) Uani 1 1 d . . . . .
H35A H 0.067828 0.799112 0.348630 0.070 Uiso 1 1 calc R U . . .
H35B H 0.031423 0.878570 0.347551 0.070 Uiso 1 1 calc R U . . .
C36 C 0.10590(11) 0.9090(3) 0.43320(19) 0.0937(11) Uani 1 1 d . . . . .
H36A H 0.093370 0.955483 0.458454 0.112 Uiso 1 1 calc R U . . .
H36B H 0.123740 0.860433 0.477553 0.112 Uiso 1 1 calc R U . . .
C37 C 0.22791(12) 1.0423(3) 0.1434(2) 0.1002(12) Uani 1 1 d . . . . .
H37A H 0.254575 1.087105 0.177879 0.120 Uiso 1 1 calc R U . . .
H37B H 0.215958 1.052703 0.080508 0.120 Uiso 1 1 calc R U . . .
C38 C 0.24659(15) 0.9444(3) 0.1688(3) 0.1112(14) Uani 1 1 d . . . . .
H38A H 0.249305 0.913709 0.121222 0.133 Uiso 1 1 calc R U . . .
H38B H 0.279381 0.943916 0.222514 0.133 Uiso 1 1 calc R U . . .
N1 N 0.17504(6) 1.05288(12) 0.31805(11) 0.0412(4) Uani 1 1 d . . . . .
N2 N 0.19982(6) 0.88884(13) 0.33451(10) 0.0427(4) Uani 1 1 d . . . . .
N3 N 0.12270(6) 0.85226(13) 0.19905(11) 0.0458(4) Uani 1 1 d . . . . .
N4 N 0.10296(6) 1.01773(13) 0.17437(11) 0.0447(4) Uani 1 1 d . . . . .
O1 O 0.21131(6) 0.89893(13) 0.18342(10) 0.0614(5) Uani 1 1 d . . . . .
O2 O 0.18821(6) 1.05320(13) 0.16154(10) 0.0613(5) Uani 1 1 d . . . . .
O3 O 0.06590(5) 0.91321(11) 0.28029(9) 0.0467(4) Uani 1 1 d . . . . .
O4 O 0.13749(5) 0.95106(11) 0.40764(9) 0.0472(4) 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 N2 1.454(3) . ?
C1 N1 1.475(3) . ?
C1 C6 1.536(3) . ?
C1 H1 0.9800 . ?
C2 N1 1.465(2) . ?
C2 N4 1.484(3) . ?
C2 C5 1.520(3) . ?
C2 H2 0.9800 . ?
C3 N4 1.455(3) . ?
C3 N3 1.465(3) . ?
C3 C6 1.532(3) . ?
C3 H3 0.9800 . ?
C4 N3 1.463(3) . ?
C4 N2 1.473(3) . ?
C4 C5 1.533(3) . ?
C4 H4 0.9800 . ?
C5 O3 1.421(2) . ?
C5 O4 1.429(2) . ?
C6 O2 1.417(3) . ?
C6 O1 1.417(3) . ?
C7 N1 1.457(3) . ?
C7 C8 1.509(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C13 1.360(4) . ?
C8 C9 1.373(3) . ?
C9 C10 1.373(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.356(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.363(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 N2 1.461(3) . ?
C14 C15 1.514(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.376(3) . ?
C15 C16 1.376(3) . ?
C16 C17 1.381(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 N3 1.455(3) . ?
C21 C22 1.508(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.377(4) . ?
C22 C27 1.382(4) . ?
C23 C24 1.380(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.360(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.358(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.375(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 N4 1.465(3) . ?
C28 C29 1.500(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.362(3) . ?
C29 C34 1.377(3) . ?
C30 C31 1.384(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.355(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.346(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.379(4) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 O3 1.420(3) . ?
C35 C36 1.495(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 O4 1.385(3) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 O2 1.410(3) . ?
C37 C38 1.481(5) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 O1 1.387(3) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 111.24(16) . . ?
N2 C1 C6 106.49(17) . . ?
N1 C1 C6 111.41(17) . . ?
N2 C1 H1 109.2 . . ?
N1 C1 H1 109.2 . . ?
C6 C1 H1 109.2 . . ?
N1 C2 N4 109.79(15) . . ?
N1 C2 C5 106.08(15) . . ?
N4 C2 C5 112.59(16) . . ?
N1 C2 H2 109.4 . . ?
N4 C2 H2 109.4 . . ?
C5 C2 H2 109.4 . . ?
N4 C3 N3 110.93(17) . . ?
N4 C3 C6 106.73(18) . . ?
N3 C3 C6 112.22(17) . . ?
N4 C3 H3 109.0 . . ?
N3 C3 H3 109.0 . . ?
C6 C3 H3 109.0 . . ?
N3 C4 N2 110.43(16) . . ?
N3 C4 C5 106.73(16) . . ?
N2 C4 C5 111.00(17) . . ?
N3 C4 H4 109.5 . . ?
N2 C4 H4 109.5 . . ?
C5 C4 H4 109.5 . . ?
O3 C5 O4 105.22(15) . . ?
O3 C5 C2 110.86(16) . . ?
O4 C5 C2 110.22(16) . . ?
O3 C5 C4 112.84(16) . . ?
O4 C5 C4 110.71(16) . . ?
C2 C5 C4 107.03(16) . . ?
O2 C6 O1 106.47(16) . . ?
O2 C6 C3 110.57(17) . . ?
O1 C6 C3 110.65(18) . . ?
O2 C6 C1 111.34(19) . . ?
O1 C6 C1 111.95(17) . . ?
C3 C6 C1 105.94(16) . . ?
N1 C7 C8 111.94(17) . . ?
N1 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C13 C8 C9 117.2(2) . . ?
C13 C8 C7 121.1(2) . . ?
C9 C8 C7 121.6(2) . . ?
C10 C9 C8 122.0(3) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.2(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 121.2(3) . . ?
C8 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
N2 C14 C15 111.81(17) . . ?
N2 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
N2 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C20 C15 C16 118.1(2) . . ?
C20 C15 C14 119.7(2) . . ?
C16 C15 C14 122.26(19) . . ?
C15 C16 C17 121.0(2) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.4(2) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C20 120.1(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 121.1(2) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
N3 C21 C22 112.63(19) . . ?
N3 C21 H21A 109.1 . . ?
C22 C21 H21A 109.1 . . ?
N3 C21 H21B 109.1 . . ?
C22 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C23 C22 C27 117.6(3) . . ?
C23 C22 C21 122.6(2) . . ?
C27 C22 C21 119.7(3) . . ?
C22 C23 C24 121.2(3) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C25 C24 C23 119.9(4) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C26 C25 C24 120.0(4) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.4(4) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C22 120.9(4) . . ?
C26 C27 H27 119.5 . . ?
C22 C27 H27 119.5 . . ?
N4 C28 C29 112.66(18) . . ?
N4 C28 H28A 109.1 . . ?
C29 C28 H28A 109.1 . . ?
N4 C28 H28B 109.1 . . ?
C29 C28 H28B 109.1 . . ?
H28A C28 H28B 107.8 . . ?
C30 C29 C34 117.6(2) . . ?
C30 C29 C28 121.6(2) . . ?
C34 C29 C28 120.7(2) . . ?
C29 C30 C31 120.7(3) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 H30 119.6 . . ?
C32 C31 C30 120.8(3) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C33 C32 C31 119.4(3) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C32 C33 C34 120.3(3) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C29 C34 C33 121.2(3) . . ?
C29 C34 H34 119.4 . . ?
C33 C34 H34 119.4 . . ?
O3 C35 C36 103.72(19) . . ?
O3 C35 H35A 111.0 . . ?
C36 C35 H35A 111.0 . . ?
O3 C35 H35B 111.0 . . ?
C36 C35 H35B 111.0 . . ?
H35A C35 H35B 109.0 . . ?
O4 C36 C35 106.5(2) . . ?
O4 C36 H36A 110.4 . . ?
C35 C36 H36A 110.4 . . ?
O4 C36 H36B 110.4 . . ?
C35 C36 H36B 110.4 . . ?
H36A C36 H36B 108.6 . . ?
O2 C37 C38 106.6(3) . . ?
O2 C37 H37A 110.4 . . ?
C38 C37 H37A 110.4 . . ?
O2 C37 H37B 110.4 . . ?
C38 C37 H37B 110.4 . . ?
H37A C37 H37B 108.6 . . ?
O1 C38 C37 105.5(3) . . ?
O1 C38 H38A 110.6 . . ?
C37 C38 H38A 110.6 . . ?
O1 C38 H38B 110.6 . . ?
C37 C38 H38B 110.6 . . ?
H38A C38 H38B 108.8 . . ?
C7 N1 C2 113.03(17) . . ?
C7 N1 C1 116.69(16) . . ?
C2 N1 C1 110.20(16) . . ?
C1 N2 C14 114.11(17) . . ?
C1 N2 C4 110.41(16) . . ?
C14 N2 C4 116.97(16) . . ?
C21 N3 C4 114.68(18) . . ?
C21 N3 C3 116.93(17) . . ?
C4 N3 C3 110.28(16) . . ?
C3 N4 C28 113.08(17) . . ?
C3 N4 C2 109.88(16) . . ?
C28 N4 C2 116.57(16) . . ?
C38 O1 C6 108.3(2) . . ?
C37 O2 C6 108.0(2) . . ?
C35 O3 C5 106.65(15) . . ?
C36 O4 C5 109.11(17) . . ?

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 C2 C5 O3 173.44(15) . . . . ?
N4 C2 C5 O3 -66.5(2) . . . . ?
N1 C2 C5 O4 57.36(19) . . . . ?
N4 C2 C5 O4 177.46(15) . . . . ?
N1 C2 C5 C4 -63.11(19) . . . . ?
N4 C2 C5 C4 57.0(2) . . . . ?
N3 C4 C5 O3 61.5(2) . . . . ?
N2 C4 C5 O3 -178.15(15) . . . . ?
N3 C4 C5 O4 179.10(15) . . . . ?
N2 C4 C5 O4 -60.5(2) . . . . ?
N3 C4 C5 C2 -60.75(19) . . . . ?
N2 C4 C5 C2 59.6(2) . . . . ?
N4 C3 C6 O2 -57.8(2) . . . . ?
N3 C3 C6 O2 -179.51(16) . . . . ?
N4 C3 C6 O1 -175.50(16) . . . . ?
N3 C3 C6 O1 62.8(2) . . . . ?
N4 C3 C6 C1 63.0(2) . . . . ?
N3 C3 C6 C1 -58.8(2) . . . . ?
N2 C1 C6 O2 -177.46(15) . . . . ?
N1 C1 C6 O2 61.1(2) . . . . ?
N2 C1 C6 O1 -58.4(2) . . . . ?
N1 C1 C6 O1 -179.86(16) . . . . ?
N2 C1 C6 C3 62.3(2) . . . . ?
N1 C1 C6 C3 -59.2(2) . . . . ?
N1 C7 C8 C13 -134.5(2) . . . . ?
N1 C7 C8 C9 47.5(3) . . . . ?
C13 C8 C9 C10 -1.4(4) . . . . ?
C7 C8 C9 C10 176.6(2) . . . . ?
C8 C9 C10 C11 -0.2(5) . . . . ?
C9 C10 C11 C12 1.4(5) . . . . ?
C10 C11 C12 C13 -1.0(5) . . . . ?
C9 C8 C13 C12 1.9(4) . . . . ?
C7 C8 C13 C12 -176.1(3) . . . . ?
C11 C12 C13 C8 -0.8(5) . . . . ?
N2 C14 C15 C20 152.3(2) . . . . ?
N2 C14 C15 C16 -28.1(3) . . . . ?
C20 C15 C16 C17 -1.6(4) . . . . ?
C14 C15 C16 C17 178.8(3) . . . . ?
C15 C16 C17 C18 0.5(5) . . . . ?
C16 C17 C18 C19 1.2(5) . . . . ?
C17 C18 C19 C20 -1.7(5) . . . . ?
C16 C15 C20 C19 1.1(4) . . . . ?
C14 C15 C20 C19 -179.3(2) . . . . ?
C18 C19 C20 C15 0.5(4) . . . . ?
N3 C21 C22 C23 19.3(3) . . . . ?
N3 C21 C22 C27 -164.4(2) . . . . ?
C27 C22 C23 C24 0.7(4) . . . . ?
C21 C22 C23 C24 177.1(2) . . . . ?
C22 C23 C24 C25 -1.0(4) . . . . ?
C23 C24 C25 C26 0.4(6) . . . . ?
C24 C25 C26 C27 0.3(7) . . . . ?
C25 C26 C27 C22 -0.6(6) . . . . ?
C23 C22 C27 C26 0.0(5) . . . . ?
C21 C22 C27 C26 -176.5(3) . . . . ?
N4 C28 C29 C30 -120.0(3) . . . . ?
N4 C28 C29 C34 63.2(3) . . . . ?
C34 C29 C30 C31 0.9(5) . . . . ?
C28 C29 C30 C31 -176.0(3) . . . . ?
C29 C30 C31 C32 -0.8(6) . . . . ?
C30 C31 C32 C33 0.4(6) . . . . ?
C31 C32 C33 C34 -0.1(5) . . . . ?
C30 C29 C34 C33 -0.7(4) . . . . ?
C28 C29 C34 C33 176.3(2) . . . . ?
C32 C33 C34 C29 0.3(5) . . . . ?
O3 C35 C36 O4 -17.8(3) . . . . ?
O2 C37 C38 O1 11.2(4) . . . . ?
C8 C7 N1 C2 75.9(2) . . . . ?
C8 C7 N1 C1 -154.82(17) . . . . ?
N4 C2 N1 C7 75.8(2) . . . . ?
C5 C2 N1 C7 -162.27(16) . . . . ?
N4 C2 N1 C1 -56.8(2) . . . . ?
C5 C2 N1 C1 65.16(19) . . . . ?
N2 C1 N1 C7 167.41(16) . . . . ?
C6 C1 N1 C7 -73.9(2) . . . . ?
N2 C1 N1 C2 -61.9(2) . . . . ?
C6 C1 N1 C2 56.7(2) . . . . ?
N1 C1 N2 C14 -78.8(2) . . . . ?
C6 C1 N2 C14 159.68(16) . . . . ?
N1 C1 N2 C4 55.4(2) . . . . ?
C6 C1 N2 C4 -66.16(19) . . . . ?
C15 C14 N2 C1 -74.2(2) . . . . ?
C15 C14 N2 C4 154.80(19) . . . . ?
N3 C4 N2 C1 62.8(2) . . . . ?
C5 C4 N2 C1 -55.4(2) . . . . ?
N3 C4 N2 C14 -164.50(18) . . . . ?
C5 C4 N2 C14 77.3(2) . . . . ?
C22 C21 N3 C4 78.7(2) . . . . ?
C22 C21 N3 C3 -149.90(19) . . . . ?
N2 C4 N3 C21 79.1(2) . . . . ?
C5 C4 N3 C21 -160.19(17) . . . . ?
N2 C4 N3 C3 -55.5(2) . . . . ?
C5 C4 N3 C3 65.3(2) . . . . ?
N4 C3 N3 C21 162.98(17) . . . . ?
C6 C3 N3 C21 -77.7(2) . . . . ?
N4 C3 N3 C4 -63.6(2) . . . . ?
C6 C3 N3 C4 55.7(2) . . . . ?
N3 C3 N4 C28 -76.3(2) . . . . ?
C6 C3 N4 C28 161.20(17) . . . . ?
N3 C3 N4 C2 55.9(2) . . . . ?
C6 C3 N4 C2 -66.6(2) . . . . ?
C29 C28 N4 C3 -162.46(18) . . . . ?
C29 C28 N4 C2 68.8(2) . . . . ?
N1 C2 N4 C3 63.4(2) . . . . ?
C5 C2 N4 C3 -54.5(2) . . . . ?
N1 C2 N4 C28 -166.26(17) . . . . ?
C5 C2 N4 C28 75.8(2) . . . . ?
C37 C38 O1 C6 -21.1(4) . . . . ?
O2 C6 O1 C38 23.3(3) . . . . ?
C3 C6 O1 C38 143.5(3) . . . . ?
C1 C6 O1 C38 -98.6(3) . . . . ?
C38 C37 O2 C6 2.9(4) . . . . ?
O1 C6 O2 C37 -15.7(3) . . . . ?
C3 C6 O2 C37 -136.0(2) . . . . ?
C1 C6 O2 C37 106.6(2) . . . . ?
C36 C35 O3 C5 28.8(3) . . . . ?
O4 C5 O3 C35 -29.2(2) . . . . ?
C2 C5 O3 C35 -148.33(18) . . . . ?
C4 C5 O3 C35 91.6(2) . . . . ?
C35 C36 O4 C5 0.2(3) . . . . ?
O3 C5 O4 C36 17.6(3) . . . . ?
C2 C5 O4 C36 137.2(2) . . . . ?
C4 C5 O4 C36 -104.6(2) . . . . ?

_refine_diff_density_max         0.476
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_CRB44
_audit_block_doi                 10.5517/ccdc.csd.cc2b6c1z
_database_code_depnum_ccdc_archive 'CCDC 2151060'
loop_
_audit_author_name
_audit_author_address
'Rong-bin Cai'
;Nanjing University Of Science And Technology
China
;
_audit_update_record             
;
2022-02-09 deposited with the CCDC.	2022-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(1'r,3'r,5'r,7'r)-4',8',9',10'-tetranitro-4',8',9',10'-tetraazadispiro[[1,3]dioxolane-2,2'-adamantane-6',2''-[1,3]dioxolane]
_chemical_name_common            
2,4,6,8-tetranitro-9,9,10,10-diethylenedioxy-2,4,6,8-tetrazaadamantane
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 N8 O12'
_chemical_formula_sum            'C10 H12 N8 O12'
_chemical_formula_weight         436.28

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.851(6)
_cell_length_b                   9.892(5)
_cell_length_c                   14.373(7)
_cell_angle_alpha                90
_cell_angle_beta                 114.106(6)
_cell_angle_gamma                90
_cell_volume                     1667.7(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3066
_cell_measurement_theta_min      2.6935
_cell_measurement_theta_max      26.7510

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_F_000             896
_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    0.161
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.976
_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            11663
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.795
_diffrn_reflns_theta_max         25.004
_diffrn_reflns_theta_full        25.004
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2940
_reflns_number_gt                2176
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0638P)²+0.6622P] 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         2940
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1176
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.90549(19) 0.2128(2) 0.13978(18) 0.0314(5) Uani 1 1 d . . . . .
H1 H 0.844293 0.198709 0.072038 0.038 Uiso 1 1 calc R U . . .
C2 C 1.00939(18) 0.1100(2) 0.30852(18) 0.0335(6) Uani 1 1 d . . . . .
H2 H 1.015872 0.027830 0.348664 0.040 Uiso 1 1 calc R U . . .
C3 C 1.11359(18) 0.2613(2) 0.24111(17) 0.0305(5) Uani 1 1 d . . . . .
H3 H 1.188046 0.277290 0.239389 0.037 Uiso 1 1 calc R U . . .
C4 C 0.97780(18) 0.2320(2) 0.35811(18) 0.0342(6) Uani 1 1 d . . . . .
C5 C 1.02056(19) 0.2386(2) 0.13229(18) 0.0304(5) Uani 1 1 d . . . . .
C6 C 0.96826(17) 0.3574(2) 0.29180(17) 0.0314(5) Uani 1 1 d . . . . .
H6 H 0.948897 0.437602 0.321535 0.038 Uiso 1 1 calc R U . . .
C7 C 0.8924(3) 0.2081(4) 0.4671(2) 0.0657(9) Uani 1 1 d . . . . .
H7A H 0.889606 0.116699 0.490460 0.079 Uiso 1 1 calc R U . . .
H7B H 0.835462 0.262278 0.477937 0.079 Uiso 1 1 calc R U . . .
C8 C 1.0069(3) 0.2666(4) 0.5213(2) 0.0753(11) Uani 1 1 d . . . . .
H8A H 1.001537 0.361327 0.536354 0.090 Uiso 1 1 calc R U . . .
H8B H 1.048200 0.218998 0.584791 0.090 Uiso 1 1 calc R U . . .
C9 C 1.0743(3) 0.1757(3) 0.0064(2) 0.0605(8) Uani 1 1 d . . . . .
H9A H 1.041510 0.117514 -0.052849 0.073 Uiso 1 1 calc R U . . .
H9B H 1.156092 0.180554 0.026822 0.073 Uiso 1 1 calc R U . . .
C10 C 1.0232(3) 0.3106(3) -0.0156(2) 0.0681(10) Uani 1 1 d . . . . .
H10A H 1.071773 0.372368 -0.032207 0.082 Uiso 1 1 calc R U . . .
H10B H 0.949224 0.307292 -0.072710 0.082 Uiso 1 1 calc R U . . .
N1 N 0.92108(15) 0.09314(18) 0.20333(14) 0.0329(5) Uani 1 1 d . . . . .
N2 N 1.11718(15) 0.14146(19) 0.30383(15) 0.0336(5) Uani 1 1 d . . . . .
N3 N 0.88013(15) 0.32984(18) 0.19124(14) 0.0309(5) Uani 1 1 d . . . . .
N4 N 1.07812(14) 0.37731(18) 0.28248(14) 0.0317(5) Uani 1 1 d . . . . .
N5 N 0.82063(18) 0.0256(2) 0.19622(18) 0.0461(6) Uani 1 1 d . . . . .
N6 N 1.18683(18) 0.0336(2) 0.30129(16) 0.0429(6) Uani 1 1 d . . . . .
N7 N 0.83372(16) 0.4441(2) 0.12910(17) 0.0396(5) Uani 1 1 d . . . . .
N8 N 1.16457(17) 0.4403(2) 0.36686(16) 0.0395(5) Uani 1 1 d . . . . .
O1 O 0.87332(14) 0.20823(18) 0.36358(13) 0.0443(5) Uani 1 1 d . . . . .
O2 O 1.06200(14) 0.25218(19) 0.45582(13) 0.0456(5) Uani 1 1 d . . . . .
O3 O 1.04840(14) 0.12697(15) 0.08767(12) 0.0369(4) Uani 1 1 d . . . . .
O4 O 1.01209(14) 0.35290(15) 0.07341(12) 0.0372(4) Uani 1 1 d . . . . .
O5 O 0.73220(16) 0.0577(2) 0.12685(16) 0.0651(6) Uani 1 1 d . . . . .
O6 O 0.83363(18) -0.0630(2) 0.25820(17) 0.0657(6) Uani 1 1 d . . . . .
O7 O 1.27091(16) 0.0636(2) 0.28769(16) 0.0588(6) Uani 1 1 d . . . . .
O8 O 1.15966(18) -0.07845(19) 0.31759(17) 0.0646(6) Uani 1 1 d . . . . .
O9 O 0.77234(16) 0.4214(2) 0.04021(15) 0.0572(6) Uani 1 1 d . . . . .
O10 O 0.85516(16) 0.55372(18) 0.17020(15) 0.0532(5) Uani 1 1 d . . . . .
O11 O 1.13437(17) 0.5352(2) 0.40321(16) 0.0613(6) Uani 1 1 d . . . . .
O12 O 1.26146(14) 0.39897(19) 0.39266(14) 0.0497(5) 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 1.458(3) . ?
C1 N3 1.480(3) . ?
C1 C5 1.547(3) . ?
C1 H1 0.9800 . ?
C2 N2 1.448(3) . ?
C2 N1 1.483(3) . ?
C2 C4 1.539(3) . ?
C2 H2 0.9800 . ?
C3 N4 1.449(3) . ?
C3 N2 1.479(3) . ?
C3 C5 1.549(3) . ?
C3 H3 0.9800 . ?
C4 O2 1.393(3) . ?
C4 O1 1.397(3) . ?
C4 C6 1.538(3) . ?
C5 O4 1.390(3) . ?
C5 O3 1.395(3) . ?
C6 N3 1.452(3) . ?
C6 N4 1.485(3) . ?
C6 H6 0.9800 . ?
C7 O1 1.405(3) . ?
C7 C8 1.474(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O2 1.397(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O3 1.424(3) . ?
C9 C10 1.463(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O4 1.408(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N1 N5 1.420(3) . ?
N2 N6 1.403(3) . ?
N3 N7 1.412(3) . ?
N4 N8 1.412(3) . ?
N5 O5 1.209(3) . ?
N5 O6 1.211(3) . ?
N6 O7 1.211(3) . ?
N6 O8 1.213(3) . ?
N7 O10 1.212(3) . ?
N7 O9 1.217(3) . ?
N8 O11 1.213(3) . ?
N8 O12 1.216(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 N3 108.89(19) . . ?
N1 C1 C5 106.67(17) . . ?
N3 C1 C5 108.52(17) . . ?
N1 C1 H1 110.9 . . ?
N3 C1 H1 110.9 . . ?
C5 C1 H1 110.9 . . ?
N2 C2 N1 108.96(19) . . ?
N2 C2 C4 106.92(18) . . ?
N1 C2 C4 108.87(18) . . ?
N2 C2 H2 110.7 . . ?
N1 C2 H2 110.7 . . ?
C4 C2 H2 110.7 . . ?
N4 C3 N2 108.75(18) . . ?
N4 C3 C5 106.68(17) . . ?
N2 C3 C5 108.55(17) . . ?
N4 C3 H3 110.9 . . ?
N2 C3 H3 110.9 . . ?
C5 C3 H3 110.9 . . ?
O2 C4 O1 109.64(19) . . ?
O2 C4 C6 109.99(19) . . ?
O1 C4 C6 109.61(18) . . ?
O2 C4 C2 109.63(18) . . ?
O1 C4 C2 109.59(19) . . ?
C6 C4 C2 108.37(19) . . ?
O4 C5 O3 109.58(19) . . ?
O4 C5 C1 109.70(17) . . ?
O3 C5 C1 109.48(17) . . ?
O4 C5 C3 109.45(17) . . ?
O3 C5 C3 110.01(17) . . ?
C1 C5 C3 108.61(19) . . ?
N3 C6 N4 108.60(18) . . ?
N3 C6 C4 107.31(18) . . ?
N4 C6 C4 108.94(17) . . ?
N3 C6 H6 110.6 . . ?
N4 C6 H6 110.6 . . ?
C4 C6 H6 110.6 . . ?
O1 C7 C8 105.3(2) . . ?
O1 C7 H7A 110.7 . . ?
C8 C7 H7A 110.7 . . ?
O1 C7 H7B 110.7 . . ?
C8 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
O2 C8 C7 105.9(2) . . ?
O2 C8 H8A 110.5 . . ?
C7 C8 H8A 110.5 . . ?
O2 C8 H8B 110.5 . . ?
C7 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
O3 C9 C10 104.6(2) . . ?
O3 C9 H9A 110.8 . . ?
C10 C9 H9A 110.8 . . ?
O3 C9 H9B 110.8 . . ?
C10 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
O4 C10 C9 106.1(2) . . ?
O4 C10 H10A 110.5 . . ?
C9 C10 H10A 110.5 . . ?
O4 C10 H10B 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
N5 N1 C1 116.67(18) . . ?
N5 N1 C2 114.88(19) . . ?
C1 N1 C2 113.57(17) . . ?
N6 N2 C2 118.04(19) . . ?
N6 N2 C3 117.10(19) . . ?
C2 N2 C3 114.12(17) . . ?
N7 N3 C6 115.80(18) . . ?
N7 N3 C1 115.60(18) . . ?
C6 N3 C1 113.76(17) . . ?
N8 N4 C3 115.66(18) . . ?
N8 N4 C6 115.13(18) . . ?
C3 N4 C6 113.72(17) . . ?
O5 N5 O6 126.7(2) . . ?
O5 N5 N1 117.2(2) . . ?
O6 N5 N1 116.1(2) . . ?
O7 N6 O8 127.0(2) . . ?
O7 N6 N2 116.0(2) . . ?
O8 N6 N2 116.9(2) . . ?
O10 N7 O9 126.7(2) . . ?
O10 N7 N3 117.0(2) . . ?
O9 N7 N3 116.2(2) . . ?
O11 N8 O12 126.6(2) . . ?
O11 N8 N4 115.7(2) . . ?
O12 N8 N4 117.5(2) . . ?
C4 O1 C7 107.7(2) . . ?
C4 O2 C8 107.2(2) . . ?
C5 O3 C9 107.40(18) . . ?
C5 O4 C10 107.45(19) . . ?

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
N2 C2 C4 O2 -60.4(2) . . . . ?
N1 C2 C4 O2 -177.95(17) . . . . ?
N2 C2 C4 O1 179.25(17) . . . . ?
N1 C2 C4 O1 61.7(2) . . . . ?
N2 C2 C4 C6 59.7(2) . . . . ?
N1 C2 C4 C6 -57.9(2) . . . . ?
N1 C1 C5 O4 -179.28(17) . . . . ?
N3 C1 C5 O4 -62.1(2) . . . . ?
N1 C1 C5 O3 60.5(2) . . . . ?
N3 C1 C5 O3 177.63(17) . . . . ?
N1 C1 C5 C3 -59.7(2) . . . . ?
N3 C1 C5 C3 57.5(2) . . . . ?
N4 C3 C5 O4 60.2(2) . . . . ?
N2 C3 C5 O4 177.19(17) . . . . ?
N4 C3 C5 O3 -179.40(17) . . . . ?
N2 C3 C5 O3 -62.4(2) . . . . ?
N4 C3 C5 C1 -59.6(2) . . . . ?
N2 C3 C5 C1 57.4(2) . . . . ?
O2 C4 C6 N3 179.60(17) . . . . ?
O1 C4 C6 N3 -59.8(2) . . . . ?
C2 C4 C6 N3 59.8(2) . . . . ?
O2 C4 C6 N4 62.2(2) . . . . ?
O1 C4 C6 N4 -177.19(17) . . . . ?
C2 C4 C6 N4 -57.6(2) . . . . ?
O1 C7 C8 O2 -20.6(4) . . . . ?
O3 C9 C10 O4 22.4(4) . . . . ?
N3 C1 N1 N5 81.8(2) . . . . ?
C5 C1 N1 N5 -161.25(19) . . . . ?
N3 C1 N1 C2 -55.3(2) . . . . ?
C5 C1 N1 C2 61.6(2) . . . . ?
N2 C2 N1 N5 162.93(18) . . . . ?
C4 C2 N1 N5 -80.8(2) . . . . ?
N2 C2 N1 C1 -59.1(2) . . . . ?
C4 C2 N1 C1 57.1(2) . . . . ?
N1 C2 N2 N6 -87.7(2) . . . . ?
C4 C2 N2 N6 154.81(19) . . . . ?
N1 C2 N2 C3 55.8(2) . . . . ?
C4 C2 N2 C3 -61.7(2) . . . . ?
N4 C3 N2 N6 -157.30(18) . . . . ?
C5 C3 N2 N6 87.0(2) . . . . ?
N4 C3 N2 C2 58.8(2) . . . . ?
C5 C3 N2 C2 -56.9(2) . . . . ?
N4 C6 N3 N7 -81.2(2) . . . . ?
C4 C6 N3 N7 161.16(18) . . . . ?
N4 C6 N3 C1 56.3(2) . . . . ?
C4 C6 N3 C1 -61.3(2) . . . . ?
N1 C1 N3 N7 -163.98(17) . . . . ?
C5 C1 N3 N7 80.3(2) . . . . ?
N1 C1 N3 C6 58.4(2) . . . . ?
C5 C1 N3 C6 -57.3(2) . . . . ?
N2 C3 N4 N8 81.5(2) . . . . ?
C5 C3 N4 N8 -161.64(18) . . . . ?
N2 C3 N4 C6 -55.1(2) . . . . ?
C5 C3 N4 C6 61.8(2) . . . . ?
N3 C6 N4 N8 163.51(18) . . . . ?
C4 C6 N4 N8 -79.9(2) . . . . ?
N3 C6 N4 C3 -59.7(2) . . . . ?
C4 C6 N4 C3 56.8(2) . . . . ?
C1 N1 N5 O5 12.1(3) . . . . ?
C2 N1 N5 O5 148.7(2) . . . . ?
C1 N1 N5 O6 -171.0(2) . . . . ?
C2 N1 N5 O6 -34.5(3) . . . . ?
C2 N2 N6 O7 173.3(2) . . . . ?
C3 N2 N6 O7 30.8(3) . . . . ?
C2 N2 N6 O8 -10.1(3) . . . . ?
C3 N2 N6 O8 -152.5(2) . . . . ?
C6 N3 N7 O10 -13.2(3) . . . . ?
C1 N3 N7 O10 -149.9(2) . . . . ?
C6 N3 N7 O9 169.7(2) . . . . ?
C1 N3 N7 O9 33.0(3) . . . . ?
C3 N4 N8 O11 -178.2(2) . . . . ?
C6 N4 N8 O11 -42.2(3) . . . . ?
C3 N4 N8 O12 5.2(3) . . . . ?
C6 N4 N8 O12 141.1(2) . . . . ?
O2 C4 O1 C7 -2.3(3) . . . . ?
C6 C4 O1 C7 -123.1(2) . . . . ?
C2 C4 O1 C7 118.1(2) . . . . ?
C8 C7 O1 C4 13.9(4) . . . . ?
O1 C4 O2 C8 -11.1(3) . . . . ?
C6 C4 O2 C8 109.5(3) . . . . ?
C2 C4 O2 C8 -131.4(2) . . . . ?
C7 C8 O2 C4 19.3(4) . . . . ?
O4 C5 O3 C9 8.5(3) . . . . ?
C1 C5 O3 C9 128.8(2) . . . . ?
C3 C5 O3 C9 -111.9(2) . . . . ?
C10 C9 O3 C5 -18.8(3) . . . . ?
O3 C5 O4 C10 6.0(3) . . . . ?
C1 C5 O4 C10 -114.2(2) . . . . ?
C3 C5 O4 C10 126.7(2) . . . . ?
C9 C10 O4 C5 -17.7(3) . . . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.071


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
