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_7062209
_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         'C15 H18 N26 O16, C2 H3 N'
_chemical_formula_sum            'C17 H21 N27 O16'
_chemical_formula_weight         859.61
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-05-02
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_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            8
_cell_length_a                   8.0773(2)
_cell_length_b                   24.2356(5)
_cell_length_c                   31.9915(7)
_cell_measurement_reflns_used    18398
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.7930
_cell_measurement_theta_min      3.9000
_cell_volume                     6262.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_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 0.981
_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    -65.00 -22.00   0.50   12.00    --  -48.76  66.00 149.00   86
  2  \w    -63.00 -38.00   0.50   35.00    --  -90.00  55.00 -37.00   50
  3  \w     40.00  65.00   0.50   35.00    --  111.50 -66.00  14.00   50
  4  \w     41.00  77.00   0.50   35.00    --  111.50-122.00 -53.00   72
  5  \w     65.00  97.00   0.50   35.00    --  111.50-151.00 145.00   64
  6  \w    131.00 158.00   0.50   35.00    --  111.50  66.00 149.00   54
  7  \w    114.00 139.00   0.50   35.00    --  111.50  55.00 -37.00   50
  8  \w   -114.00 -83.00   0.50   12.00    --  -48.76-125.00 120.00   62
  9  \w   -121.00 -39.00   0.50   12.00    --  -48.76 -38.00  30.00  164
 10  \w   -112.00 -74.00   0.50   12.00    --  -48.76-125.00  90.00   76
 11  \w    -51.00 -26.00   0.50   35.00    --  -90.00  45.00-120.00   50
 12  \w     41.00  89.00   0.50   35.00    --  111.50 -78.00 167.15   96
 13  \w    140.00 175.00   0.50   35.00    --  111.50  30.00  60.00   70
 14  \w     54.00 103.00   0.50   35.00    --  111.50 -95.00 -60.00   98
 15  \w    124.00 155.00   0.50   35.00    --  111.50  77.00  60.00   62
 16  \w    143.00 178.00   0.50   35.00    --  111.50  29.00 -48.34   70
 17  \w    100.00 157.00   0.50   35.00    --  111.50  52.00  89.77  114
 18  \w     43.00  68.00   0.50   35.00    --  111.50 -95.00 -90.00   50
 19  \w     43.00  72.00   0.50   35.00    --  111.50 -78.00   9.92   58
 20  \w     48.00  84.00   0.50   35.00    --  111.50-125.00-120.00   72
 21  \w    135.00 161.00   0.50   35.00    --  111.50  30.00 -30.00   52
 22  \w     79.00 105.00   0.50   35.00    --  111.50 -77.00  60.00   52
 23  \w     40.00  74.00   0.50   35.00    --  111.50 -77.00  60.00   68
 24  \w     40.00  96.00   0.50   35.00    --  111.50 -95.00 150.00  112
 25  \w    101.00 129.00   0.50   35.00    --  111.50  29.00 -48.34   56
 26  \w    108.00 134.00   0.50   35.00    --  111.50  30.00 -30.00   52
 27  \w     40.00  66.00   0.50   35.00    --  111.50 -61.00  30.00   52
 28  \w     44.00  69.00   0.50   35.00    --  111.50 -61.00-150.00   50
 29  \w     45.00  71.00   0.50   35.00    --  111.50 -77.00-120.00   52
 30  \w     74.00  99.00   0.50   35.00    --  111.50 -95.00 -30.00   50
 31  \w    102.00 128.00   0.50   35.00    --  111.50  45.00 -30.00   52
 32  \w     98.00 124.00   0.50   35.00    --  111.50 125.00  60.00   52
 33  \w     57.00  83.00   0.50   35.00    --  111.50 -95.00   0.00   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      0.0417331000
_diffrn_orient_matrix_UB_12      -0.0617038000
_diffrn_orient_matrix_UB_13      -0.0049690000
_diffrn_orient_matrix_UB_21      0.1192379000
_diffrn_orient_matrix_UB_22      0.0139742000
_diffrn_orient_matrix_UB_23      -0.0360659000
_diffrn_orient_matrix_UB_31      0.1428963000
_diffrn_orient_matrix_UB_32      0.0063314000
_diffrn_orient_matrix_UB_33      0.0315025000
_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  0.0789
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            42994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.199
_diffrn_reflns_theta_min         3.648
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.415
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             3520
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         6726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0591
_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/[\s^2^(Fo^2^)+(0.0928P)^2^+5.2137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1639
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5719
_reflns_number_total             6726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05332b2.cif
_cod_data_source_block           9
_cod_depositor_comments
'Adding full bibliography for 7062208--7062213.cif.'
_cod_database_code               7062209
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     SNV7039
_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)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B), C15(H15A,H15B)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              45173
_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 2.863
_oxdiff_exptl_absorpt_empirical_full_min 0.403