#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/37/1553798.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1553798
loop_
_publ_author_name
'Hou, Tianjiao'
'Zhang, Jian'
'Wang, Chenjiao'
'Luo, Jun'
_publ_section_title
;
 A facile method to construct a 2,4,9-triazaadamantane skeleton and
 synthesize nitramine derivatives
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1819
_journal_paper_doi               10.1039/C7QO00357A
_journal_volume                  4
_journal_year                    2017
_chemical_formula_sum            'C7 H9 N7 O9'
_chemical_formula_weight         335.21
_chemical_name_systematic
'2,4,9-trinitro-2,4,9-triazaadamantane-7-yl nitrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-03-14 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.870(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6272(7)
_cell_length_b                   13.3952(13)
_cell_length_c                   11.8460(12)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.51
_cell_volume                     1210.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5528
_diffrn_reflns_point_group_measured_fraction_full 0.895
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.469
_diffrn_reflns_theta_min         3.495
_exptl_absorpt_coefficient_mu    0.170
_exptl_crystal_colour            ????
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_description       ???
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ??'
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.038
_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)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2653
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0407P)²+0.3657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0686
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.806
_reflns_Friedel_fraction_max     0.753
_reflns_number_gt                2606
_reflns_number_total             2653
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7qo00357a2.cif
_cod_data_source_block           20161018CY01_0m_a
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1553798
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.963
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'
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
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
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
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)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 141471937
