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_7062213
_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         'C17 H18 N26 O28, 5(C2 H3 N)'
_chemical_formula_sum            'C27 H33 N31 O28'
_chemical_formula_weight         1239.84
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-09-22
_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                 103.7058(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.0971(2)
_cell_length_b                   11.66535(8)
_cell_length_c                   36.7954(3)
_cell_measurement_reflns_used    72632
_cell_measurement_temperature    100.1(1)
_cell_measurement_theta_max      77.8210
_cell_measurement_theta_min      2.4130
_cell_volume                     10882.72(15)
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.1(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_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    -63.00  23.00   0.50    0.30    --  -48.70  63.00 -22.00  172
  2  \w   -114.00 -33.00   0.50    0.30    --  -48.70 -63.00-159.00  162
  3  \w     41.00  68.00   0.50    0.30    --   48.70  63.00 -22.00   54
  4  \w      7.00  38.00   0.50    0.30    --   48.70 -63.00-159.00   62
  5  \w   -138.00-113.00   0.50    1.00    --  -86.25 -63.00-159.00   50
  6  \w    -68.00 -43.00   0.50    1.00    --  -86.25  63.00 -22.00   50
  7  \w     93.00 123.00   0.50    1.00    --  107.75  63.00 -22.00   60
  8  \w     37.00  62.00   0.50    1.00    --  107.75 -63.00-159.00   50
  9  \w   -107.00 -77.00   0.50    0.30    --  -48.70-125.00 -90.00   60
 10  \w    -25.00  22.00   0.50    0.30    --  -48.70  19.00 120.00   94
 11  \w    -46.00 -20.00   0.50    1.00    --  -86.25  45.00-180.00   52
 12  \w    -51.00 -26.00   0.50    1.00    --  -86.25  45.00 120.00   50
 13  \w     36.00  61.00   0.50    1.00    --  107.75 -61.00-120.00   50
 14  \w     97.00 133.00   0.50    1.00    --  107.75  44.00  88.45   72
 15  \w    146.00 178.00   0.50    1.00    --  107.75  15.00 -90.00   64
 16  \w     47.00 107.00   0.50    1.00    --  107.75-105.00  67.39  120
 17  \w     42.00 102.00   0.50    1.00    --  107.75 -95.00  30.00  120
 18  \w     47.00  90.00   0.50    1.00    --  107.75 -77.00-120.00   86
 19  \w    104.00 150.00   0.50    1.00    --  107.75  45.00 -30.00   92
 20  \w    121.00 168.00   0.50    1.00    --  107.75 125.00-150.00   94
 21  \w     40.00  71.00   0.50    1.00    --  107.75-108.00 106.23   62
 22  \w    119.00 178.00   0.50    1.00    --  107.75  15.00  60.00  118
 23  \w    126.00 178.00   0.50    1.00    --  107.75  61.00 -90.00  104
 24  \w     44.00  70.00   0.50    1.00    --  107.75 -61.00 -90.00   52
 25  \w     97.00 123.00   0.50    1.00    --  107.75  61.00 -90.00   52
 26  \w     40.00 109.00   0.50    1.00    --  107.75-114.00 -45.37  138
 27  \w     36.00  96.00   0.50    1.00    --  107.75 -93.00-116.93  120
 28  \w     36.00  69.00   0.50    1.00    --  107.75 -77.00 -60.00   66
 29  \w     72.00  98.00   0.50    1.00    --  107.75 -77.00 -60.00   52
 30  \w     99.00 124.00   0.50    1.00    --  107.75  15.00-120.00   50
 31  \w    120.00 157.00   0.50    1.00    --  107.75 101.00 128.85   74
 32  \w     51.00  93.00   0.50    1.00    --  107.75-127.00 -12.71   84
 33  \w     86.00 124.00   0.50    1.00    --  107.75  77.00 150.00   76
 34  \w    136.00 162.00   0.50    1.00    --  107.75  77.00 150.00   52
 35  \w     40.00  92.00   0.50    1.00    --  107.75 -95.00   0.00  104
 36  \w     77.00 104.00   0.50    1.00    --  107.75-108.00 106.23   54
 37  \w     88.00 121.00   0.50    1.00    --  107.75  77.00-180.00   66
 38  \w     41.00  80.00   0.50    1.00    --  107.75 -77.00  30.00   78
 39  \w     38.00  63.00   0.50    1.00    --  107.75 -61.00-180.00   50
 40  \w    134.00 160.00   0.50    1.00    --  107.75  44.00  88.45   52
 41  \w     98.00 175.00   0.50    1.00    --  107.75  30.00-180.00  154
 42  \w    134.00 161.00   0.50    1.00    --  107.75 125.00  30.00   54
 43  \w     51.00  77.00   0.50    1.00    --  107.75 -77.00  60.00   52
 44  \w     39.00  89.00   0.50    1.00    --  107.75 -77.00 150.00  100
 45  \w     45.00  71.00   0.50    1.00    --  107.75 -95.00  90.00   52
 46  \w     41.00  67.00   0.50    1.00    --  107.75-112.00   4.33   52
 47  \w     36.00  66.00   0.50    1.00    --  107.75 -61.00  30.00   60
 48  \w     40.00  66.00   0.50    1.00    --  107.75-125.00 -60.00   52
 49  \w    135.00 175.00   0.50    1.00    --  107.75  45.00-150.00   80
 50  \w    139.00 175.00   0.50    1.00    --  107.75  45.00 120.00   72
 51  \w    149.00 176.00   0.50    1.00    --  107.75 125.00 -30.00   54
 52  \w     95.00 121.00   0.50    1.00    --  107.75  77.00-150.00   52
 53  \w     43.00  69.00   0.50    1.00    --  107.75 -87.00 146.33   52
 54  \w    112.00 138.00   0.50    1.00    --  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      -0.0423772000
_diffrn_orient_matrix_UB_12      0.0010744000
_diffrn_orient_matrix_UB_13      -0.0371250000
_diffrn_orient_matrix_UB_21      -0.0292022000
_diffrn_orient_matrix_UB_22      0.0972989000
_diffrn_orient_matrix_UB_23      0.0150090000
_diffrn_orient_matrix_UB_31      0.0323047000
_diffrn_orient_matrix_UB_32      0.0892670000
_diffrn_orient_matrix_UB_33      -0.0159339000
_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  0.0523
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            150991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.807
_diffrn_reflns_theta_min         2.472
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             5088
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1559
_refine_ls_number_reflns         23017
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+9.4340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1456
_reflns_Friedel_coverage         0.000
_reflns_number_gt                20188
_reflns_number_total             23017
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05332b2.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 7062208--7062213.cif.'
_cod_original_cell_volume        10882.72(14)
_cod_database_code               7062213
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C12H12N12O12
_chemical_oxdiff_usercomment     NSV2022
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.770
_reflns_odcompleteness_completeness 93.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     86.18
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.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), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C23(H23), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B), C16(H16A,H16B), C24(H24A,H24B), C31(H31A,H31B),
 C33(H33A,H33B)
2.c Idealised Me refined as rotating group:
 C61(H61A,H61B,H61C), C63(H63A,H63B,H63C), C65(H65A,H65B,H65C), C67(H67A,H67B,
 H67C), C69(H69A,H69B,H69C), C71(H71A,H71B,H71C), C73(H73A,H73B,H73C), C74(H74A,
 H74B,H74C), C79(H79A,H79B,H79C), C81(H81A,H81B,H81C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              76731
_shelx_fab_checksum              9668
_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 1.475
_oxdiff_exptl_absorpt_empirical_full_min 0.597