# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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. 
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data_20161018CY01_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1537833'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'2,4,9-trinitro-2,4,9-triazaadamantane-7-yl nitrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H9 N7 O9'
_chemical_formula_weight         335.21

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'
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           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   7.6272(7)
_cell_length_b                   13.3952(13)
_cell_length_c                   11.8460(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.870(3)
_cell_angle_gamma                90
_cell_volume                     1210.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.52

_exptl_crystal_description       ???
_exptl_crystal_colour            ????
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.963
_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            5528
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.495
_diffrn_reflns_theta_max         28.469
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_point_group_measured_fraction_full 0.895
_reflns_number_total             2653
_reflns_number_gt                2606
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_max     0.753
_reflns_Friedel_fraction_full    0.806

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0407P)²+0.3657P] 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 1104 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2653
_refine_ls_number_parameters     208
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0686
_refine_ls_wR_factor_gt          0.0682
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.3670(2) 0.63735(11) 0.76663(12) 0.0235(3) Uani 1 1 d . . . . .
O2 O 0.6182(2) 0.71222(11) 0.78426(12) 0.0240(3) Uani 1 1 d . . . . .
O9 O 0.68219(18) 0.52138(10) 0.31353(12) 0.0202(3) Uani 1 1 d . . . . .
O6 O 0.7674(2) 0.89002(11) 0.60956(14) 0.0283(3) Uani 1 1 d . . . . .
O5 O 0.5866(2) 0.94613(11) 0.48034(15) 0.0268(3) Uani 1 1 d . . . . .
O4 O 0.10298(19) 0.71535(13) 0.59173(14) 0.0266(3) Uani 1 1 d . . . . .
O8 O 0.8975(2) 0.46229(13) 0.21581(14) 0.0321(4) Uani 1 1 d . . . . .
N2 N 0.5064(2) 0.66705(12) 0.73038(13) 0.0173(3) Uani 1 1 d . . . . .
O7 O 0.8919(2) 0.62262(12) 0.24514(14) 0.0306(4) Uani 1 1 d . . . . .
O3 O 0.2165(2) 0.85218(11) 0.52561(16) 0.0331(4) Uani 1 1 d . . . . .
N1 N 0.5466(2) 0.64123(11) 0.61893(13) 0.0149(3) Uani 1 1 d . . . . .
N3 N 0.3358(2) 0.70427(11) 0.48080(14) 0.0161(3) Uani 1 1 d . . . . .
N6 N 0.6575(2) 0.87880(11) 0.53464(14) 0.0176(3) Uani 1 1 d . . . . .
N5 N 0.6126(2) 0.78340(11) 0.50651(14) 0.0192(3) Uani 1 1 d . . . . .
N7 N 0.8386(2) 0.53826(14) 0.25372(14) 0.0225(3) Uani 1 1 d . . . . .
N4 N 0.2117(2) 0.76163(12) 0.53810(15) 0.0209(3) Uani 1 1 d . . . . .
C4 C 0.7689(2) 0.62823(13) 0.47646(15) 0.0151(3) Uani 1 1 d . . . . .
H4A H 0.8629 0.6625 0.4382 0.018 Uiso 1 1 calc R U . . .
H4B H 0.8168 0.5689 0.5122 0.018 Uiso 1 1 calc R U . . .
C7 C 0.4007(2) 0.61502(12) 0.54121(15) 0.0143(3) Uani 1 1 d . . . . .
H7 H 0.3057 0.5823 0.5819 0.017 Uiso 1 1 calc R U . . .
C2 C 0.4764(2) 0.54528(13) 0.45206(15) 0.0152(3) Uani 1 1 d . . . . .
H2A H 0.5211 0.4851 0.4877 0.018 Uiso 1 1 calc R U . . .
H2B H 0.3854 0.5265 0.3980 0.018 Uiso 1 1 calc R U . . .
C3 C 0.5498(3) 0.69180(13) 0.33269(16) 0.0173(3) Uani 1 1 d . . . . .
H3A H 0.4584 0.6726 0.2791 0.021 Uiso 1 1 calc R U . . .
H3B H 0.6414 0.7261 0.2921 0.021 Uiso 1 1 calc R U . . .
C1 C 0.6244(2) 0.59946(12) 0.39180(15) 0.0141(3) Uani 1 1 d . . . . .
C5 C 0.6885(2) 0.69688(12) 0.56545(15) 0.0141(3) Uani 1 1 d . . . . .
H5A H 0.7770 0.7178 0.6214 0.017 Uiso 1 1 calc R U . . .
C6 C 0.4742(2) 0.76063(13) 0.42386(15) 0.0167(3) Uani 1 1 d . . . . .
H6 H 0.4270 0.8220 0.3901 0.020 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 N2 1.220(2) . ?
O2 N2 1.218(2) . ?
O9 N7 1.415(2) . ?
O9 C1 1.470(2) . ?
O6 N6 1.221(2) . ?
O5 N6 1.229(2) . ?
O4 N4 1.221(2) . ?
O8 N7 1.202(2) . ?
N2 N1 1.403(2) . ?
O7 N7 1.206(2) . ?
O3 N4 1.223(2) . ?
N1 C5 1.466(2) . ?
N1 C7 1.476(2) . ?
N3 N4 1.402(2) . ?
N3 C6 1.470(2) . ?
N3 C7 1.475(2) . ?
N6 N5 1.363(2) . ?
N5 C6 1.461(2) . ?
N5 C5 1.468(2) . ?
C4 C1 1.528(2) . ?
C4 C5 1.534(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C7 C2 1.530(2) . ?
C7 H7 0.9800 . ?
C2 C1 1.528(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C1 1.527(2) . ?
C3 C6 1.539(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 H5A 0.9800 . ?
C6 H6 0.9800 . ?

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
N7 O9 C1 117.74(13) . . ?
O1 N2 O2 125.79(17) . . ?
O1 N2 N1 117.06(16) . . ?
O2 N2 N1 117.01(16) . . ?
N2 N1 C5 117.03(14) . . ?
N2 N1 C7 118.18(15) . . ?
C5 N1 C7 113.95(14) . . ?
N4 N3 C6 115.81(14) . . ?
N4 N3 C7 115.67(15) . . ?
C6 N3 C7 113.63(14) . . ?
O6 N6 O5 125.62(16) . . ?
O6 N6 N5 117.42(16) . . ?
O5 N6 N5 116.93(17) . . ?
N6 N5 C6 122.42(15) . . ?
N6 N5 C5 121.87(16) . . ?
C6 N5 C5 115.45(13) . . ?
O8 N7 O7 129.35(18) . . ?
O8 N7 O9 111.97(16) . . ?
O7 N7 O9 118.66(16) . . ?
O4 N4 O3 126.04(18) . . ?
O4 N4 N3 116.25(15) . . ?
O3 N4 N3 117.60(18) . . ?
C1 C4 C5 108.09(14) . . ?
C1 C4 H4A 110.1 . . ?
C5 C4 H4A 110.1 . . ?
C1 C4 H4B 110.1 . . ?
C5 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
N3 C7 N1 110.75(13) . . ?
N3 C7 C2 106.70(14) . . ?
N1 C7 C2 106.69(14) . . ?
N3 C7 H7 110.8 . . ?
N1 C7 H7 110.8 . . ?
C2 C7 H7 110.8 . . ?
C1 C2 C7 108.76(13) . . ?
C1 C2 H2A 109.9 . . ?
C7 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
C7 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C1 C3 C6 107.72(14) . . ?
C1 C3 H3A 110.2 . . ?
C6 C3 H3A 110.2 . . ?
C1 C3 H3B 110.2 . . ?
C6 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
O9 C1 C3 113.61(15) . . ?
O9 C1 C4 111.91(14) . . ?
C3 C1 C4 110.89(14) . . ?
O9 C1 C2 100.81(12) . . ?
C3 C1 C2 109.03(15) . . ?
C4 C1 C2 110.10(15) . . ?
N1 C5 N5 108.58(15) . . ?
N1 C5 C4 107.31(13) . . ?
N5 C5 C4 107.78(14) . . ?
N1 C5 H5A 111.0 . . ?
N5 C5 H5A 111.0 . . ?
C4 C5 H5A 111.0 . . ?
N5 C6 N3 108.44(15) . . ?
N5 C6 C3 108.73(15) . . ?
N3 C6 C3 107.07(15) . . ?
N5 C6 H6 110.8 . . ?
N3 C6 H6 110.8 . . ?
C3 C6 H6 110.8 . . ?

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
O1 N2 N1 C5 164.57(15) . . . . ?
O2 N2 N1 C5 -19.5(2) . . . . ?
O1 N2 N1 C7 22.4(2) . . . . ?
O2 N2 N1 C7 -161.71(15) . . . . ?
O6 N6 N5 C6 175.65(18) . . . . ?
O5 N6 N5 C6 -6.0(3) . . . . ?
O6 N6 N5 C5 1.7(3) . . . . ?
O5 N6 N5 C5 -179.93(17) . . . . ?
C1 O9 N7 O8 162.15(17) . . . . ?
C1 O9 N7 O7 -19.4(3) . . . . ?
C6 N3 N4 O4 -175.40(16) . . . . ?
C7 N3 N4 O4 -38.8(2) . . . . ?
C6 N3 N4 O3 8.1(2) . . . . ?
C7 N3 N4 O3 144.67(18) . . . . ?
N4 N3 C7 N1 -84.71(19) . . . . ?
C6 N3 C7 N1 52.81(19) . . . . ?
N4 N3 C7 C2 159.55(15) . . . . ?
C6 N3 C7 C2 -62.93(18) . . . . ?
N2 N1 C7 N3 90.90(18) . . . . ?
C5 N1 C7 N3 -52.43(18) . . . . ?
N2 N1 C7 C2 -153.35(14) . . . . ?
C5 N1 C7 C2 63.32(17) . . . . ?
N3 C7 C2 C1 59.58(18) . . . . ?
N1 C7 C2 C1 -58.84(18) . . . . ?
N7 O9 C1 C3 73.2(2) . . . . ?
N7 O9 C1 C4 -53.3(2) . . . . ?
N7 O9 C1 C2 -170.31(15) . . . . ?
C6 C3 C1 O9 173.04(14) . . . . ?
C6 C3 C1 C4 -59.90(19) . . . . ?
C6 C3 C1 C2 61.49(18) . . . . ?
C5 C4 C1 O9 -171.07(13) . . . . ?
C5 C4 C1 C3 60.95(18) . . . . ?
C5 C4 C1 C2 -59.81(18) . . . . ?
C7 C2 C1 O9 178.53(14) . . . . ?
C7 C2 C1 C3 -61.66(18) . . . . ?
C7 C2 C1 C4 60.21(19) . . . . ?
N2 N1 C5 N5 -91.21(18) . . . . ?
C7 N1 C5 N5 52.56(17) . . . . ?
N2 N1 C5 C4 152.54(14) . . . . ?
C7 N1 C5 C4 -63.69(18) . . . . ?
N6 N5 C5 N1 118.77(18) . . . . ?
C6 N5 C5 N1 -55.6(2) . . . . ?
N6 N5 C5 C4 -125.28(18) . . . . ?
C6 N5 C5 C4 60.4(2) . . . . ?
C1 C4 C5 N1 59.04(17) . . . . ?
C1 C4 C5 N5 -57.73(18) . . . . ?
N6 N5 C6 N3 -118.29(18) . . . . ?
C5 N5 C6 N3 56.0(2) . . . . ?
N6 N5 C6 C3 125.62(18) . . . . ?
C5 N5 C6 C3 -60.1(2) . . . . ?
N4 N3 C6 N5 83.91(18) . . . . ?
C7 N3 C6 N5 -53.55(19) . . . . ?
N4 N3 C6 C3 -158.93(15) . . . . ?
C7 N3 C6 C3 63.61(18) . . . . ?
C1 C3 C6 N5 56.62(19) . . . . ?
C1 C3 C6 N3 -60.34(18) . . . . ?

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.038



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ??'
