#------------------------------------------------------------------------------
#$Date: 2020-05-23 08:03:10 +0300 (Sat, 23 May 2020) $
#$Revision: 252312 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/21/2022130.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022130
loop_
_publ_author_name
'Domasevitch, Kostiantyn V.'
'Senchyk, Ganna A.'
'Krautscheid, Harald'
_publ_section_title
;
 Bulk polarity of 3,5,7-trinitro-1-azaadamantane mediated by asymmetric
 NO₂(lone pair)···NO₂(π-hole) supramolecular
 bonding
;
_journal_coeditor_code           VP3006
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620006762
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C9 H12 N4 O6'
_chemical_formula_moiety         'C9 H12 N4 O6'
_chemical_formula_sum            'C9 H12 N4 O6'
_chemical_formula_weight         272.23
_chemical_name_common
;
3,5,7-Trinitro-1-azaadamantane
;
_chemical_name_systematic
;
2,5,7-Trinitro-1-azatricyclo[3.3.1.13.7]decane
;
_space_group_crystal_system      trigonal
_space_group_IT_number           143
_space_group_name_Hall           'P 3'
_space_group_name_H-M_alt        'P 3'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   12.7917(14)
_cell_length_b                   12.7917(14)
_cell_length_c                   5.8996(6)
_cell_measurement_reflns_used    5172
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29.187
_cell_measurement_theta_min      3.185
_cell_volume                     836.01(15)
_computing_cell_refinement
;
IPDS (Stoe & Cie, 2000)
;
_computing_data_collection
;
IPDS (Stoe & Cie, 2000)
;
_computing_data_reduction
;
IPDS (Stoe & Cie, 2000)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
WinGX (Farrugia, 1999)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Stoe Image plate diffraction system IPDS-2T'
_diffrn_measurement_method       'φ oscillation scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5172
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.187
_diffrn_reflns_theta_min         3.185
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7919
_exptl_absorpt_correction_T_min  0.6540
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
[X-RED (Stoe & Cie, 2001) and X-SHAPE (Stoe & Cie, 1999)]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_description       prism
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2961
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0321
_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)+(0.0330P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0602
_refine_ls_wR_factor_ref         0.0632
_reflns_number_gt                2451
_reflns_number_total             2961
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vp3006sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        836.0(2)
_cod_database_code               2022130
_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   0.970
_shelx_estimated_absorpt_t_max   0.977
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1A 0.2573(3) 0.2891(2) -0.2900(6) 0.0475(7) Uani d 1 . .
O O2A 0.3275(2) 0.1737(3) -0.1919(5) 0.0413(6) Uani d 1 . .
N N1A 0.000000 0.000000 0.1998(7) 0.0183(9) Uani d 1 . .
N N2A 0.2452(3) 0.1945(3) -0.2164(4) 0.0267(6) Uani d 1 . .
C C1A 0.1201(3) 0.0952(3) 0.1220(5) 0.0205(6) Uani d 1 . .
C C2A 0.1207(3) 0.0967(3) -0.1406(5) 0.0196(6) Uani d 1 . .
C C3A 0.0253(3) 0.1249(3) -0.2281(5) 0.0203(6) Uani d 1 . .
H H1A 0.182(3) 0.077(3) 0.183(5) 0.019(8) Uiso d 1 . .
H H2A 0.131(3) 0.167(4) 0.173(6) 0.017(8) Uiso d 1 . .
H H3A 0.039(3) 0.197(4) -0.180(5) 0.011(8) Uiso d 1 . .
H H4A 0.024(3) 0.118(3) -0.396(6) 0.018(8) Uiso d 1 . .
O O1B 0.3760(2) 0.3259(3) 0.2319(5) 0.0362(6) Uani d 1 . .
O O2B 0.5076(3) 0.4797(3) 0.0412(6) 0.0488(8) Uani d 1 . .
N N1B 0.666667 0.333333 0.5825(7) 0.0224(10) Uani d 1 . .
N N2B 0.4789(3) 0.3926(3) 0.1637(4) 0.0259(6) Uani d 1 . .
C C1B 0.5760(3) 0.3643(3) 0.5048(5) 0.0241(6) Uani d 1 . .
C C2B 0.5754(3) 0.3651(3) 0.2425(5) 0.0178(6) Uani d 1 . .
C C3B 0.5402(3) 0.2387(3) 0.1525(5) 0.0183(6) Uani d 1 . .
H H1B 0.599(3) 0.443(4) 0.554(5) 0.016(8) Uiso d 1 . .
H H2B 0.506(3) 0.312(3) 0.567(5) 0.008(7) Uiso d 1 . .
H H3B 0.466(3) 0.182(3) 0.207(5) 0.012(8) Uiso d 1 . .
H H4B 0.549(4) 0.243(3) -0.006(6) 0.024(9) Uiso d 1 . .
O O1C 0.1491(3) 0.3784(3) 0.2511(5) 0.0462(7) Uani d 1 . .
O O2C 0.0360(3) 0.3839(3) 0.5158(6) 0.0521(9) Uani d 1 . .
N N1C 0.333333 0.666667 0.8362(8) 0.0264(11) Uani d 1 . .
N N2C 0.1322(3) 0.4261(2) 0.4153(5) 0.0264(6) Uani d 1 . .
C C1C 0.2356(3) 0.5486(3) 0.7592(5) 0.0248(7) Uani d 1 . .
C C2C 0.2346(3) 0.5470(3) 0.4983(5) 0.0201(6) Uani d 1 . .
C C3C 0.3551(3) 0.5649(3) 0.4084(5) 0.0205(6) Uani d 1 . .
H H1C 0.160(4) 0.543(3) 0.807(6) 0.025(9) Uiso d 1 . .
H H2C 0.245(4) 0.484(4) 0.813(6) 0.024(9) Uiso d 1 . .
H H3C 0.347(3) 0.562(3) 0.242(5) 0.010(8) Uiso d 1 . .
H H4C 0.370(3) 0.504(3) 0.463(5) 0.014(7) Uiso d 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1A N1A C1A 3 2 110.82(19) ?
C1A N1A C1A 3 . 110.82(19) ?
C1A N1A C1A 2 . 110.82(19) ?
O2A N2A O1A . . 124.4(3) ?
O2A N2A C2A . . 116.7(3) ?
O1A N2A C2A . . 118.9(3) ?
N1A C1A C2A . . 108.5(3) ?
N1A C1A H1A . . 108(2) ?
C2A C1A H1A . . 111.4(19) ?
N1A C1A H2A . . 107(2) ?
C2A C1A H2A . . 109(2) ?
H1A C1A H2A . . 112(3) ?
N2A C2A C3A . . 109.8(3) ?
N2A C2A C3A . 3 108.5(3) ?
C3A C2A C3A . 3 111.8(3) ?
N2A C2A C1A . . 107.5(2) ?
C3A C2A C1A . . 110.0(3) ?
C3A C2A C1A 3 . 109.1(3) ?
C2A C3A C2A . 2 106.6(3) ?
C2A C3A H3A . . 112(2) ?
C2A C3A H3A 2 . 111(2) ?
C2A C3A H4A . . 107(2) ?
C2A C3A H4A 2 . 107.5(19) ?
H3A C3A H4A . . 113(3) ?
C1B N1B C1B 2_655 3_665 110.8(2) ?
C1B N1B C1B 2_655 . 110.8(2) ?
C1B N1B C1B 3_665 . 110.8(2) ?
O2B N2B O1B . . 124.0(3) ?
O2B N2B C2B . . 119.0(3) ?
O1B N2B C2B . . 117.0(3) ?
N1B C1B C2B . . 108.7(3) ?
N1B C1B H1B . . 109(2) ?
C2B C1B H1B . . 107.5(19) ?
N1B C1B H2B . . 108(2) ?
C2B C1B H2B . . 114.3(19) ?
H1B C1B H2B . . 109(3) ?
N2B C2B C3B . 3_665 110.2(2) ?
N2B C2B C3B . . 107.1(2) ?
C3B C2B C3B 3_665 . 111.0(3) ?
N2B C2B C1B . . 108.4(2) ?
C3B C2B C1B 3_665 . 110.3(2) ?
C3B C2B C1B . . 109.7(3) ?
C2B C3B C2B 2_655 . 106.2(3) ?
C2B C3B H3B 2_655 . 109(2) ?
C2B C3B H3B . . 110(2) ?
C2B C3B H4B 2_655 . 106(2) ?
C2B C3B H4B . . 108(2) ?
H3B C3B H4B . . 116(3) ?
C1C N1C C1C . 3_565 110.9(2) ?
C1C N1C C1C . 2_665 110.9(2) ?
C1C N1C C1C 3_565 2_665 110.9(2) ?
O1C N2C O2C . . 123.7(3) ?
O1C N2C C2C . . 119.1(3) ?
O2C N2C C2C . . 117.2(3) ?
N1C C1C C2C . . 108.7(3) ?
N1C C1C H1C . . 107(2) ?
C2C C1C H1C . . 107(2) ?
N1C C1C H2C . . 112(2) ?
C2C C1C H2C . . 109(2) ?
H1C C1C H2C . . 113(3) ?
N2C C2C C3C . 3_565 107.1(2) ?
N2C C2C C3C . . 109.2(3) ?
C3C C2C C3C 3_565 . 111.1(3) ?
N2C C2C C1C . . 109.4(3) ?
C3C C2C C1C 3_565 . 109.8(2) ?
C3C C2C C1C . . 110.0(3) ?
C2C C3C C2C 2_665 . 106.2(3) ?
C2C C3C H3C 2_665 . 113(2) ?
C2C C3C H3C . . 104.9(18) ?
C2C C3C H4C 2_665 . 109(2) ?
C2C C3C H4C . . 111(2) ?
H3C C3C H4C . . 112(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1A N2A . 1.220(4) ?
O2A N2A . 1.217(4) ?
N1A C1A 3 1.478(3) ?
N1A C1A 2 1.478(3) ?
N1A C1A . 1.478(3) ?
N2A C2A . 1.519(4) ?
C1A C2A . 1.549(4) ?
C1A H1A . 1.00(4) ?
C1A H2A . 0.91(4) ?
C2A C3A . 1.525(5) ?
C2A C3A 3 1.534(4) ?
C3A H3A . 0.89(4) ?
C3A H4A . 0.99(3) ?
O1B N2B . 1.225(4) ?
O2B N2B . 1.219(4) ?
N1B C1B 2_655 1.473(4) ?
N1B C1B 3_665 1.473(4) ?
N1B C1B . 1.473(4) ?
N2B C2B . 1.517(4) ?
C1B C2B . 1.548(4) ?
C1B H1B . 0.94(4) ?
C1B H2B . 0.89(3) ?
C2B C3B 3_665 1.523(4) ?
C2B C3B . 1.540(4) ?
C3B H3B . 0.92(3) ?
C3B H4B . 0.94(4) ?
O1C N2C . 1.220(4) ?
O2C N2C . 1.222(4) ?
N1C C1C . 1.470(4) ?
N1C C1C 3_565 1.470(4) ?
N1C C1C 2_665 1.470(4) ?
N2C C2C . 1.524(4) ?
C1C C2C . 1.539(4) ?
C1C H1C . 0.97(4) ?
C1C H2C . 0.95(4) ?
C2C C3C 3_565 1.532(4) ?
C2C C3C . 1.535(5) ?
C3C H3C . 0.99(3) ?
C3C H4C . 0.94(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1A H2A O1C . 0.90(4) 2.64(4) 3.536(5) 170(3) yes
C3A H4A N1A 1_554 0.99(3) 2.76(3) 3.678(5) 154(3) yes
C1B H1B O2C 2_665 0.94(4) 2.58(4) 3.455(5) 154(3) yes
C1B H2B O2A 1_556 0.89(3) 2.51(3) 3.392(4) 170(2) yes
C3B H4B N1B 1_554 0.94(4) 2.79(4) 3.664(5) 156(3) yes
C1C H1C O2B 4_566 0.98(4) 2.56(4) 3.496(4) 161(3) yes
C1C H2C O1A 1_556 0.96(4) 2.64(4) 3.479(5) 147(3) yes
C3C H4C O1A 1_556 0.94(4) 2.80(3) 3.574(4) 140(3) yes
C3C H4C O1B . 0.94(4) 2.69(3) 3.365(4) 129(2) yes
C3C H3C N1C 1_554 0.98(3) 2.79(3) 3.678(5) 150(3) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1A N1A C1A C2A 3 . . . 62.2(3) ?
C1A N1A C1A C2A 2 . . . -61.3(3) ?
O2A N2A C2A C3A . . . . -168.0(3) ?
O1A N2A C2A C3A . . . . 14.4(4) ?
O2A N2A C2A C3A . . . 3 -45.5(4) ?
O1A N2A C2A C3A . . . 3 136.9(3) ?
O2A N2A C2A C1A . . . . 72.4(4) ?
O1A N2A C2A C1A . . . . -105.2(4) ?
N1A C1A C2A N2A . . . . -179.6(2) ?
N1A C1A C2A C3A . . . . 60.9(3) ?
N1A C1A C2A C3A . . . 3 -62.1(3) ?
N2A C2A C3A C2A . . . 2 -178.8(2) ?
C3A C2A C3A C2A 3 . . 2 60.7(4) ?
C1A C2A C3A C2A . . . 2 -60.7(3) ?
C1B N1B C1B C2B 2_655 . . . -61.9(3) ?
C1B N1B C1B C2B 3_665 . . . 61.4(3) ?
O2B N2B C2B C3B . . . 3_665 1.6(4) ?
O1B N2B C2B C3B . . . 3_665 -177.1(3) ?
O2B N2B C2B C3B . . . . -119.2(3) ?
O1B N2B C2B C3B . . . . 62.0(3) ?
O2B N2B C2B C1B . . . . 122.4(3) ?
O1B N2B C2B C1B . . . . -56.3(4) ?
N1B C1B C2B N2B . . . . 178.0(2) ?
N1B C1B C2B C3B . . . 3_665 -61.2(3) ?
N1B C1B C2B C3B . . . . 61.4(3) ?
N2B C2B C3B C2B . . . 2_655 -177.4(2) ?
C3B C2B C3B C2B 3_665 . . 2_655 62.2(4) ?
C1B C2B C3B C2B . . . 2_655 -60.0(3) ?
C1C N1C C1C C2C 3_565 . . . 62.0(3) ?
C1C N1C C1C C2C 2_665 . . . -61.7(3) ?
O1C N2C C2C C3C . . . 3_565 100.4(3) ?
O2C N2C C2C C3C . . . 3_565 -77.8(4) ?
O1C N2C C2C C3C . . . . -20.1(4) ?
O2C N2C C2C C3C . . . . 161.7(3) ?
O1C N2C C2C C1C . . . . -140.6(3) ?
O2C N2C C2C C1C . . . . 41.2(4) ?
N1C C1C C2C N2C . . . . -178.9(2) ?
N1C C1C C2C C3C . . . 3_565 -61.6(3) ?
N1C C1C C2C C3C . . . . 61.1(3) ?
N2C C2C C3C C2C . . . 2_665 180.0(2) ?
C3C C2C C3C C2C 3_565 . . 2_665 62.0(4) ?
C1C C2C C3C C2C . . . 2_665 -59.9(3) ?

_cod_database_fobs_code 2022130
