Linking polynitro hexaazaisowurtzitane cages via an N,N'-methylene bridge: a promising strategy for designing energetic ensembles of CL-20 derivatives and adjusting their properties
Parakhin, Vladimir V.; Pokhvisneva, Galina V.; Ternikova, Tatyana V.; Shlykova, Nina I.; Samigullina, Aida I.; Nikitin, Sergei V.; Gordeev, Pavel B.; Smirnov, Gennady A.; Kon’kova, Tatyana S.; Lempert, David B.; Pivkina, Alla N.; New Journal of Chemistry 47 (2023) 2444–2455; doi:10.1039/D2NJ05332B

data_7062210
_publ_section_title
;
 Linking polynitro hexaazaisowurtzitane cages via an N,N'-methylene
 bridge: a promising strategy for designing energetic ensembles of CL-20
 derivatives and adjusting their properties
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2444
_journal_page_last               2455
_journal_paper_doi               10.1039/D2NJ05332B
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C13 H14 N22 O18'
_chemical_formula_sum            'C13 H14 N22 O18'
_chemical_formula_weight         766.46
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-09-06
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2022-09-22 deposited with the CCDC.	2022-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   21.46514(4)
_cell_length_b                   21.46514(4)
_cell_length_c                   26.19638(11)
_cell_measurement_reflns_used    62530
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.5950
_cell_measurement_theta_min      2.6430
_cell_volume                     12070.04(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -121.00 -37.00   0.50    1.10    --  -48.68 -32.00   9.00  168
  2  \w    -24.00  37.00   0.50    1.10    --   48.68 -32.00   9.00  122
  3  \w   -159.00 -75.00   0.50    4.00    --  -86.25 -32.00   9.00  168
  4  \w     97.00 178.00   0.50    4.00    --  107.75  32.00 168.00  162
  5  \w    -37.00  24.00   0.50    1.10    --  -48.68  32.00 168.00  122
  6  \w    -26.00  26.00   0.50    1.10    --  -48.68  19.00 -60.00  104
  7  \w     27.00 120.00   0.50    1.10    --   48.68  77.00 -90.00  186
  8  \w     35.00 120.00   0.50    1.10    --   48.68  57.00 -90.00  170
  9  \w     39.00 121.00   0.50    1.10    --   48.68  38.00-150.00  164
 10  \w   -158.00 -64.00   0.50    4.00    --  -86.25 -77.00 -90.00  188
 11  \w   -158.00 -67.00   0.50    4.00    --  -86.25 -71.00-109.35  182
 12  \w   -158.00 -65.00   0.50    4.00    --  -86.25 -75.00 -82.21  186
 13  \w   -158.00 -71.00   0.50    4.00    --  -86.25 -61.00 -90.00  174
 14  \w     97.00 178.00   0.50    4.00    --  107.75  30.00 120.00  162
 15  \w     86.00 178.00   0.50    4.00    --  107.75  77.00-150.00  184
 16  \w     93.00 178.00   0.50    4.00    --  107.75  61.00 -60.00  170
 17  \w     97.00 178.00   0.50    4.00    --  107.75  15.00-150.00  162
 18  \w     36.00  71.00   0.50    4.00    --  107.75 -61.00   0.00   70
 19  \w     36.00  71.00   0.50    4.00    --  107.75 -61.00 -30.00   70
 20  \w     86.00 178.00   0.50    4.00    --  107.75  77.00 -90.00  184
 21  \w     95.00 178.00   0.50    4.00    --  107.75 125.00  30.00  166
 22  \w     93.00 178.00   0.50    4.00    --  107.75  61.00-120.00  170
 23  \w     95.00 178.00   0.50    4.00    --  107.75 125.00  60.00  166
 24  \w     36.00  71.00   0.50    4.00    --  107.75 -61.00-120.00   70
 25  \w     97.00 178.00   0.50    4.00    --  107.75  15.00  60.00  162
 26  \w     95.00 178.00   0.50    4.00    --  107.75  61.00  60.00  166
 27  \w    118.00 160.00   0.50    4.00    --  107.75  77.00-120.00   84
 28  \w     93.00 167.00   0.50    4.00    --  107.75  61.00 -90.00  148
 29  \w     93.00 141.00   0.50    4.00    --  107.75  77.00 -60.00   96
 30  \w     87.00 113.00   0.50    4.00    --  107.75  77.00-120.00   52
 31  \w     37.00  64.00   0.50    4.00    --  107.75 -77.00 -60.00   54
 32  \w     77.00 102.00   0.50    4.00    --  107.75 -77.00 -60.00   50
 33  \w     42.00  68.00   0.50    4.00    --  107.75 -77.00   0.00   52
 34  \w     63.00  88.00   0.50    4.00    --  107.75 -77.00  30.00   50
 35  \w     37.00  66.00   0.50    4.00    --  107.75-125.00-180.00   58
 36  \w     97.00 128.00   0.50    4.00    --  107.75  45.00 -60.00   62
 37  \w    127.00 178.00   0.50    4.00    --  107.75 125.00   0.00  102
 38  \w    135.00 161.00   0.50    4.00    --  107.75  15.00 -90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0654815000
_diffrn_orient_matrix_UB_12      0.0293472000
_diffrn_orient_matrix_UB_13      -0.0004313000
_diffrn_orient_matrix_UB_21      -0.0265011000
_diffrn_orient_matrix_UB_22      -0.0595912000
_diffrn_orient_matrix_UB_23      -0.0245201000
_diffrn_orient_matrix_UB_31      -0.0126598000
_diffrn_orient_matrix_UB_32      -0.0271523000
_diffrn_orient_matrix_UB_33      0.0534632000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            104285
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.881
_diffrn_reflns_theta_min         2.661
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.386
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             6240
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         6421
_refine_ls_number_restraints     100
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0528P)^2^+20.4205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1119
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6055
_reflns_number_total             6421
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05332b2.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 7062208--7062213.cif.'
_cod_original_cell_volume        12070.04(7)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7062210
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     PGV2037
_shelx_estimated_absorpt_t_max   0.885
_shelx_estimated_absorpt_t_min   0.741
_reflns_odcompleteness_completeness 98.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.52
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N5-O9 \\sim N5-O9A
 with sigma of 0.04
 N7B-N1 \\sim N1-N7 \\sim N1-N7B
 with sigma of 0.02
 N5-N11 \\sim N5-N11A
 with sigma of 0.02
 O9-N11 \\sim O9A-N11A
 with sigma of 0.02
 N2-N8 \\sim N2-N8A
 with sigma of 0.02
 N13-N19 \\sim N13-N19A
 with sigma of 0.02
 N16-O20 \\sim N16-O20A
 with sigma of 0.04
 N16-N22 \\sim N16-N22A \\sim N16-N22B
 with sigma of 0.02
 N22-O20 \\sim N22A-O20A \\sim N22B-O20B
 with sigma of 0.02
 O3-N8 \\sim O3A-N8A
 with sigma of 0.02
 O3-N2 \\sim O3A-N2
 with sigma of 0.04
 O4-N8 \\sim O4A-N8A
 with sigma of 0.02
 O3-O4 \\sim O3A-O4A
 with sigma of 0.04
 O4-N2 \\sim O4A-N2
 with sigma of 0.04
 N1-O1 \\sim N1-O1A
 with sigma of 0.04
 N7B-O1B \\sim N7-O1 \\sim N7A-O1A
 with sigma of 0.02
 N1-O2 \\sim N1-O2A
 with sigma of 0.04
 O2B-N7B \\sim O2-N7 \\sim O2A-N7A
 with sigma of 0.02
 O2-O1 \\sim O2A-O1A
 with sigma of 0.04
 O13-N19 \\sim O13A-N19A
 with sigma of 0.02
 O13-N13 \\sim O13A-N13
 with sigma of 0.04
 N19-O14 \\sim N19A-O14A
 with sigma of 0.02
 O13-O14 \\sim O13A-O14A
 with sigma of 0.04
 N13-O14 \\sim N13-O14A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(O7) \\sim Ueq: with sigma of 0.0008 and sigma for terminal atoms of 0.0016
Uanis(O4A) \\sim Ueq, Uanis(O4) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O1A) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(O1B) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(O2B) \\sim Ueq, Uanis(O2A) \\sim Ueq, Uanis(O2) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(O14A) \\sim Ueq, Uanis(O14) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(O9) = Uanis(O9A)
Uanis(N7) = Uanis(N7A) = Uanis(N7B)
Uanis(N11A) = Uanis(N11)
Uanis(N8A) = Uanis(N8)
Uanis(N19A) = Uanis(N19)
Uanis(O20A) = Uanis(O20B) = Uanis(O20)
Uanis(N22) = Uanis(N22A) = Uanis(N22B)
Uanis(O3A) = Uanis(O3)
Uanis(O4) = Uanis(O4A)
Uanis(O1) = Uanis(O1B) = Uanis(O1A)
Uanis(O2) = Uanis(O2A) = Uanis(O2B)
Uanis(O13A) = Uanis(O13)
Uanis(O14A) = Uanis(O14)
4. Others
 1*[Sof(O1)+Sof(O2)+Sof(N7)]+1*[Sof(O1A)+Sof(O2A)+Sof(N7A)]+1*[Sof(O1B)+
 Sof(O2B)+Sof(N7B)]=1 with esd of 0.0001
 1*[Sof(O20)+Sof(N22)]+1*[Sof(O20A)+Sof(N22A)]+1*[Sof(O20B)+Sof(N22B)]=1 with
 esd of 0.0001
 Sof(O1)=Sof(O2)=Sof(N7)=FVAR(1)
 Sof(O9A)=Sof(N11A)=1-FVAR(2)
 Sof(O9)=Sof(N11)=FVAR(2)
 Sof(O20)=Sof(N22)=FVAR(3)
 Sof(O1A)=Sof(O2A)=Sof(N7A)=FVAR(4)
 Sof(O1B)=Sof(O2B)=Sof(N7B)=FVAR(5)
 Sof(O3A)=Sof(O4A)=Sof(N8A)=1-FVAR(6)
 Sof(O3)=Sof(O4)=Sof(N8)=FVAR(6)
 Sof(O13A)=Sof(O14A)=Sof(N19A)=1-FVAR(7)
 Sof(O13)=Sof(O14)=Sof(N19)=FVAR(7)
 Sof(O20A)=Sof(N22A)=FVAR(8)
 Sof(O20B)=Sof(N22B)=FVAR(9)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10),
 C11(H11), C12(H12), C13(H13)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              59026
_shelx_fab_checksum              857
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.445
_oxdiff_exptl_absorpt_empirical_full_min 0.880