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_7062211
_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 O19'
_chemical_formula_sum            'C13 H14 N22 O19'
_chemical_formula_weight         782.46
_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             2022-09-01
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2022-09-27 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                   21.53830(10)
_cell_length_b                   21.53830(10)
_cell_length_c                   26.3607(2)
_cell_measurement_reflns_used    41236
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      77.6180
_cell_measurement_theta_min      2.5970
_cell_volume                     12228.69(12)
_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      99.98(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 0.991
_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   -119.00 -94.00   0.50    5.00    --  -48.68-133.00-152.00   50
  2  \w    -91.00 -21.00   0.50    5.00    --  -48.68 137.00  92.00  140
  3  \w    -81.00 -45.00   0.50    5.00    --  -48.68 -19.00-108.00   72
  4  \w    -24.00   1.00   0.50    5.00    --  -48.68  19.00  58.00   50
  5  \w     57.00  82.00   0.50    5.00    --   48.68  19.00  58.00   50
  6  \w    -81.00 -56.00   0.50   18.00    --  -86.25 137.00  92.00   50
  7  \w   -137.00-112.00   0.50   18.00    --  -86.25-133.00-152.00   50
  8  \w   -118.00 -93.00   0.50   18.00    --  -86.25 -19.00-108.00   50
  9  \w   -145.00-120.00   0.50   18.00    --  -86.25-106.00 101.00   50
 10  \w     43.00  70.00   0.50   18.00    --  107.75-133.00-152.00   54
 11  \w     71.00  96.00   0.50   18.00    --  107.75-106.00 101.00   50
 12  \w    103.00 133.00   0.50   18.00    --  107.75 137.00  92.00   60
 13  \w    113.00 138.00   0.50   18.00    --  107.75  19.00  58.00   50
 14  \w     80.00 105.00   0.50   18.00    --  107.75-137.00  29.00   50
 15  \w     80.00 117.00   0.50   18.00    --  107.75-133.00-152.00   74
 16  \w    -64.00 -35.00   0.50    5.00    --  -48.68 -57.00 150.00   58
 17  \w    -69.00 -37.00   0.50    5.00    --  -48.68 -57.00 120.00   64
 18  \w    -59.00 -27.00   0.50    5.00    --  -48.68 -77.00 120.00   64
 19  \w     40.00  94.00   0.50    5.00    --   48.68  19.00 150.00  108
 20  \w     39.00 118.00   0.50    5.00    --   48.68  38.00-180.00  158
 21  \w    -90.00 -64.00   0.50   18.00    --  -86.25 -77.00 120.00   52
 22  \w    -96.00 -69.00   0.50   18.00    --  -86.25 -66.00 176.72   54
 23  \w    -89.00 -64.00   0.50   18.00    --  -86.25 -77.00 150.00   50
 24  \w    -94.00 -65.00   0.50   18.00    --  -86.25 -77.00 137.01   58
 25  \w    -90.00 -64.00   0.50   18.00    --  -86.25 -77.00-180.00   52
 26  \w   -108.00 -66.00   0.50   18.00    --  -86.25 -72.00 159.78   84
 27  \w    125.00 151.00   0.50   18.00    --  107.75  61.00 150.00   52
 28  \w     86.00 166.00   0.50   18.00    --  107.75  77.00-180.00  160
 29  \w     37.00  62.00   0.50   18.00    --  107.75 -61.00 120.00   50
 30  \w     93.00 124.00   0.50   18.00    --  107.75  61.00 150.00   62
 31  \w    140.00 166.00   0.50   18.00    --  107.75  45.00 120.00   52
 32  \w    122.00 167.00   0.50   18.00    --  107.75  77.00 150.00   90
 33  \w     38.00  70.00   0.50   18.00    --  107.75 -61.00   0.00   64
 34  \w     37.00  69.00   0.50   18.00    --  107.75 -61.00  30.00   64
 35  \w     48.00  74.00   0.50   18.00    --  107.75 -95.00-180.00   52
 36  \w     92.00 129.00   0.50   18.00    --  107.75  77.00 120.00   74
 37  \w     95.00 168.00   0.50   18.00    --  107.75  61.00 -90.00  146
 38  \w     63.00 101.00   0.50   18.00    --  107.75 -95.00  30.00   76
 39  \w     98.00 157.00   0.50   18.00    --  107.75  15.00-120.00  118
 40  \w     95.00 143.00   0.50   18.00    --  107.75  74.00-133.05   96
 41  \w    153.00 178.00   0.50   18.00    --  107.75  74.00-133.05   50
 42  \w     64.00 103.00   0.50   18.00    --  107.75 -77.00-150.00   78
 43  \w     94.00 120.00   0.50   18.00    --  107.75  75.00  57.42   52
 44  \w    133.00 159.00   0.50   18.00    --  107.75  75.00  57.42   52
 45  \w     37.00  75.00   0.50   18.00    --  107.75 -67.00 -11.90   76
 46  \w     88.00 116.00   0.50   18.00    --  107.75  77.00 150.00   56
 47  \w     70.00 110.00   0.50   18.00    --  107.75   4.00  43.81   80
 48  \w     38.00  70.00   0.50   18.00    --  107.75 -61.00 -60.00   64
 49  \w     79.00 104.00   0.50   18.00    --  107.75 -77.00  90.00   50
 50  \w     93.00 156.00   0.50   18.00    --  107.75  61.00-180.00  126
 51  \w    106.00 132.00   0.50   18.00    --  107.75  30.00-180.00   52
 52  \w     95.00 121.00   0.50   18.00    --  107.75 -86.00 132.30   52
 53  \w     38.00  74.00   0.50   18.00    --  107.75 -77.00  90.00   72
 54  \w    110.00 135.00   0.50   18.00    --  107.75 133.00 -84.00   50
;
_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      0.0341463000
_diffrn_orient_matrix_UB_12      -0.0606024000
_diffrn_orient_matrix_UB_13      -0.0135032000
_diffrn_orient_matrix_UB_21      0.0628390000
_diffrn_orient_matrix_UB_22      0.0334564000
_diffrn_orient_matrix_UB_23      0.0060571000
_diffrn_orient_matrix_UB_31      0.0014807000
_diffrn_orient_matrix_UB_32      -0.0180615000
_diffrn_orient_matrix_UB_33      0.0565354000
_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  0.0400
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            80393
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.086
_diffrn_reflns_theta_min         2.649
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.408
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.868
_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    1.700
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             6368
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.000058(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         6509
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0534P)^2^+23.8467P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1210
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6047
_reflns_number_total             6509
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05332b2.cif
_cod_data_source_block           14
_cod_depositor_comments
'Adding full bibliography for 7062208--7062213.cif.'
_cod_original_cell_volume        12228.68(15)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7062211
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C15H17N23O18
_chemical_oxdiff_usercomment     PGV2040-needle
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.738
_reflns_odcompleteness_completeness 98.52
_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
 N13-O13 \\sim N13-O13A
 with sigma of 0.04
 N13-N19 \\sim N13-N19A \\sim N13-N19B
 with sigma of 0.02
 O13-N19 \\sim O13A-N19A \\sim O13B-N19B
 with sigma of 0.02
 N13-O14 \\sim N13-O14A
 with sigma of 0.04
 O13-O14 \\sim O13A-O14A
 with sigma of 0.04
 N19-O14 \\sim N19A-O14A \\sim N19B-O14B
 with sigma of 0.02
 O1-N7 \\sim O1A-N7A
 with sigma of 0.02
 N1-N7 \\sim N1-N7A
 with sigma of 0.02
 N7-O2 \\sim N7A-O2A
 with sigma of 0.02
 O1-N1 \\sim O1A-N1
 with sigma of 0.04
 O1-O2 \\sim O1A-O2A
 with sigma of 0.04
 N1-O2 \\sim N1-O2A
 with sigma of 0.04
 N11B-O10B \\sim O10A-N11A
 with sigma of 0.02
 O20A-N22A \\sim N22-O20
 with sigma of 0.02
 N11B-N5 \\sim N16-N22B
 with sigma of 0.02
 N5-N11A \\sim N5-N11 \\sim N22-N16 \\sim N16-N22A
 with sigma of 0.02
 N11-O9 \\sim N11-O10 \\sim N22B-O21B \\sim N22B-O20B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O2) \\sim Ueq, Uanis(O2A) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(N19A) = Uanis(N19) = Uanis(N19B)
Uanis(O13A) = Uanis(O13) = Uanis(O14A) = Uanis(O14) = Uanis(O13B) = Uanis(O14B)
Uanis(O1A) = Uanis(O1)
Uanis(N7) = Uanis(N7A)
Uanis(O2) = Uanis(O2A)
Uanis(O20A) = Uanis(O20)
Uanis(N22A) = Uanis(N22)
Uanis(O10) = Uanis(O10A)
Uanis(O10B) = Uanis(O9)
Uanis(N11) = Uanis(N11A) = Uanis(N11B)
Uanis(O20) = Uanis(O20B)
Uanis(O20B) = Uanis(O21B)
Uanis(N22A) = Uanis(N22) = Uanis(N22B)
4. Others
 1*[Sof(N11)+Sof(O10)+Sof(O9)]+1*[Sof(N11A)+Sof(O10A)]+1*[Sof(O10B)+Sof(N11B)]=
 1 with esd of 0.0001
 1*[Sof(O20)+Sof(N22)]+1*[Sof(N22A)+Sof(O20A)]+1*[Sof(O21B)+Sof(O20B)+
 Sof(N22B)]=1 with esd of 0.0001
 1*[Sof(O13)+Sof(N19)+Sof(O14)]+1*[Sof(N19A)+Sof(O14A)+Sof(O13A)]+1*[Sof(O14B)+
 Sof(N19B)+Sof(O13B)]=1 with esd of 0.0001
 1*[Sof(N11)+Sof(O10)+Sof(O9)]+1*[Sof(O21B)+Sof(O20B)+Sof(N22B)]=1 with esd of
 0.0001
 1*[Sof(O20)+Sof(N22)]+1*[Sof(N11A)+Sof(O10A)]+1*[Sof(O10B)+Sof(N11B)]+1*
 [Sof(N22A)+Sof(O20A)]=1 with esd of 0.0001
 Sof(O13)=Sof(N19)=Sof(O14)=FVAR(1)
 Sof(O20)=Sof(N22)=FVAR(2)
 Sof(N11)=Sof(O10)=Sof(O9)=FVAR(3)
 Sof(N11A)=Sof(O10A)=FVAR(4)
 Sof(O10B)=Sof(N11B)=FVAR(5)
 Sof(N22A)=Sof(O20A)=FVAR(6)
 Sof(O21B)=Sof(O20B)=Sof(N22B)=FVAR(7)
 Sof(N19A)=Sof(O14A)=Sof(O13A)=FVAR(8)
 Sof(O14B)=Sof(N19B)=Sof(O13B)=FVAR(9)
 Sof(O2A)=Sof(N7A)=Sof(O1A)=1-FVAR(10)
 Sof(O1)=Sof(N7)=Sof(O2)=FVAR(10)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C2(H2), C11(H11), C8(H8), C13(H13), C5(H5), C1(H1), C3(H3),
 C9(H9), C10(H10), C12(H12)
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              87392
_shelx_fab_checksum              83530
_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 1.771
_oxdiff_exptl_absorpt_empirical_full_min 0.701