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_7062212
_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 O20, 3.93(C2 H3 N), 0.094(H2 O)'
_chemical_formula_sum            'C20.86 H25.98 N25.93 O20.09'
_chemical_formula_weight         961.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-08-01
_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                 93.9403(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.26767(13)
_cell_length_b                   25.25063(19)
_cell_length_c                   15.55504(10)
_cell_measurement_reflns_used    50379
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.0500
_cell_measurement_theta_min      2.9050
_cell_volume                     7549.96(9)
_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 1.3 (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 0.989
_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    -84.00 -25.00   0.50    1.25    --  -48.76 119.00 -14.00  118
  2  \w   -121.00 -53.00   0.50    1.25    --  -48.76-158.00 105.00  136
  3  \w     59.00  84.00   0.50    1.25    --   48.76-158.00 105.00   50
  4  \w     47.00  73.00   0.50    1.25    --   48.76-119.00-100.00   52
  5  \w     73.00  98.00   0.50    1.25    --   48.76 158.00 139.00   50
  6  \w    -75.00 -50.00   0.50    5.01    --  -90.00 119.00 -14.00   50
  7  \w    -93.00 -68.00   0.50    5.01    --  -90.00 158.00 139.00   50
  8  \w   -143.00-118.00   0.50    5.01    --  -90.00-119.00-100.00   50
  9  \w    114.00 139.00   0.50    5.01    --  111.50 119.00 -14.00   50
 10  \w    107.00 132.00   0.50    5.01    --  111.50 158.00 139.00   50
 11  \w    104.00 130.00   0.50    5.01    --  111.50-158.00 105.00   52
 12  \w     49.00 109.00   0.50    5.01    --  111.50-119.00-100.00  120
 13  \w    -25.00  23.00   0.50    1.25    --  -48.76  19.00-180.00   96
 14  \w   -115.00 -88.00   0.50    1.25    --  -48.76-125.00 150.00   54
 15  \w    -22.00  24.00   0.50    1.25    --  -48.76  19.00 -30.00   92
 16  \w    -26.00  26.00   0.50    1.25    --  -48.76  19.00 -60.00  104
 17  \w   -121.00 -73.00   0.50    1.25    --  -48.76-125.00 -60.00   96
 18  \w   -117.00 -75.00   0.50    1.25    --  -48.76-125.00  30.00   84
 19  \w    101.00 177.00   0.50    5.01    --  111.50  15.00  60.00  152
 20  \w     79.00 109.00   0.50    5.01    --  111.50-117.00 -46.72   60
 21  \w     41.00  70.00   0.50    5.01    --  111.50 -61.00 -90.00   58
 22  \w     56.00  82.00   0.50    5.01    --  111.50 -95.00 120.00   52
 23  \w     45.00  75.00   0.50    5.01    --  111.50 -95.00  90.00   60
 24  \w     43.00  70.00   0.50    5.01    --  111.50 -61.00  30.00   54
 25  \w     98.00 124.00   0.50    5.01    --  111.50 -84.00-118.78   52
 26  \w     48.00 108.00   0.50    5.01    --  111.50-111.00 -25.77  120
 27  \w     44.00  74.00   0.50    5.01    --  111.50-117.00 -46.72   60
 28  \w     77.00 107.00   0.50    5.01    --  111.50-103.00 -93.05   60
 29  \w     46.00  73.00   0.50    5.01    --  111.50-103.00 -93.05   54
 30  \w     41.00  86.00   0.50    5.01    --  111.50 -84.00-118.78   90
 31  \w     44.00  70.00   0.50    5.01    --  111.50 -81.00  77.20   52
 32  \w     94.00 133.00   0.50    5.01    --  111.50 -81.00  77.20   78
 33  \w    104.00 152.00   0.50    5.01    --  111.50  45.00 -90.00   96
 34  \w    115.00 177.00   0.50    5.01    --  111.50  30.00 -30.00  124
 35  \w    110.00 174.00   0.50    5.01    --  111.50  79.00-113.18  128
 36  \w     51.00  76.00   0.50    5.01    --  111.50 -87.00-107.09   50
 37  \w     93.00 123.00   0.50    5.01    --  111.50 -87.00-107.09   60
 38  \w    109.00 152.00   0.50    5.01    --  111.50  30.00   0.00   86
 39  \w     70.00 105.00   0.50    5.01    --  111.50-111.00  23.50   70
 40  \w     43.00  70.00   0.50    5.01    --  111.50 -61.00-180.00   54
 41  \w     94.00 148.00   0.50    5.01    --  111.50  77.00  60.00  108
 42  \w     67.00  92.00   0.50    5.01    --  111.50-125.00  60.00   50
 43  \w    102.00 176.00   0.50    5.01    --  111.50  30.00-150.00  148
 44  \w    105.00 131.00   0.50    5.01    --  111.50  15.00  90.00   52
 45  \w     41.00  75.00   0.50    5.01    --  111.50 -77.00  30.00   68
 46  \w     76.00 102.00   0.50    5.01    --  111.50 -95.00-120.00   52
 47  \w    127.00 158.00   0.50    5.01    --  111.50  45.00-120.00   62
 48  \w    104.00 178.00   0.50    5.01    --  111.50  30.00 -60.00  148
 49  \w    116.00 145.00   0.50    5.01    --  111.50  61.00  90.00   58
 50  \w    132.00 175.00   0.50    5.01    --  111.50 125.00-150.00   86
 51  \w     46.00  72.00   0.50    5.01    --  111.50 -77.00 -90.00   52
 52  \w     69.00  95.00   0.50    5.01    --  111.50 -77.00 -60.00   52
 53  \w     68.00  96.00   0.50    5.01    --  111.50 -77.00 120.00   56
 54  \w     43.00  69.00   0.50    5.01    --  111.50 -95.00 -90.00   52
 55  \w     43.00  70.00   0.50    5.01    --  111.50 -61.00 -30.00   54
 56  \w     41.00  70.00   0.50    5.01    --  111.50 -61.00 -60.00   58
 57  \w    107.00 133.00   0.50    5.01    --  111.50  77.00 -90.00   52
 58  \w    136.00 173.00   0.50    5.01    --  111.50  77.00 -90.00   74
 59  \w     40.00  70.00   0.50    5.01    --  111.50 -61.00-120.00   60
;
_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      -0.0389647000
_diffrn_orient_matrix_UB_12      0.0327293000
_diffrn_orient_matrix_UB_13      0.0650327000
_diffrn_orient_matrix_UB_21      -0.0344147000
_diffrn_orient_matrix_UB_22      -0.0508731000
_diffrn_orient_matrix_UB_23      0.0312903000
_diffrn_orient_matrix_UB_31      0.0610090000
_diffrn_orient_matrix_UB_32      -0.0078352000
_diffrn_orient_matrix_UB_33      0.0681887000
_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  0.0411
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            108627
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.542
_diffrn_reflns_theta_min         2.299
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.323
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (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    1.692
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3947
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1229
_refine_ls_number_reflns         16231
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0620P)^2^+5.9131P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1239
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14493
_reflns_number_total             16231
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05332b2.cif
_cod_data_source_block           13
_cod_depositor_comments
'Adding full bibliography for 7062208--7062213.cif.'
_cod_database_code               7062212
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     SNI7061-1
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.806
_reflns_odcompleteness_completeness 97.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.50
_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, All O(H,H) groups
2. Restrained distances
 O28-N27 \\sim O28A-N27
 with sigma of 0.04
 N27-O27 \\sim N27-O27A
 with sigma of 0.04
 O28-O27 \\sim O28A-O27A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C51) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O27) = Uanis(O28)
Uanis(O28) = Uanis(O28A) = Uanis(O27A) = Uanis(O27)
4. Others
 Sof(O27A)=Sof(O28A)=1-FVAR(1)
 Sof(O27)=Sof(O28)=Sof(N51)=Sof(C52)=Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(H53C)=
 FVAR(1)
 Sof(O41)=Sof(H41A)=Sof(H41B)=FVAR(2)
5.a Free rotating group:
 O41(H41A,H41B)
5.b 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), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
  C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
5.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C26(H26A,H26B)
5.d Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C53(H53A,H53B,H53C), C55(H55A,H55B,H55C), C57(H57A,H57B,
 H57C), C59(H59A,H59B,H59C), C61(H61A,H61B,H61C), C63(H63A,H63B,H63C), C65(H65A,
 H65B,H65C)
;
_shelx_res_checksum              97488
_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 1.349
_oxdiff_exptl_absorpt_empirical_full_min 0.845