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_7062208
_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_absolute_configuration unk
_chemical_formula_moiety         'C13 H16 N20 O16'
_chemical_formula_sum            'C13 H16 N20 O16'
_chemical_formula_weight         708.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-06-16
_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                 101.3951(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.06669(19)
_cell_length_b                   13.5410(3)
_cell_length_c                   11.9398(2)
_cell_measurement_reflns_used    18074
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.4680
_cell_measurement_theta_min      3.2480
_cell_volume                     1278.49(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (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 0.991
_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     58.00  92.00   0.50    0.81    --  107.75-165.00 123.00   68
  2  \w     97.00 138.00   0.50    0.81    --  107.75-165.00 123.00   82
  3  \w     69.00  95.00   0.50    0.81    --  107.75-125.00  30.00   52
  4  \w     38.00  66.00   0.50    0.81    --  107.75-125.00  30.00   56
  5  \w     46.00  81.00   0.50    0.20    --   48.45-116.00 -88.00   70
  6  \w     39.00  67.00   0.50    0.81    --  107.75-125.00-150.00   56
  7  \w     75.00 102.00   0.50    0.81    --  107.75-125.00-150.00   54
  8  \w     80.00 105.00   0.50    0.81    --  107.75-116.00 -88.00   50
  9  \w     76.00 105.00   0.50    0.81    --  107.75 -95.00 -90.00   58
 10  \w     43.00  69.00   0.50    0.81    --  107.75 -95.00 -90.00   52
 11  \w     73.00  99.00   0.50    0.81    --  107.75 -95.00 -60.00   52
 12  \w     88.00 114.00   0.50    0.81    --  107.75 -87.00-135.98   52
 13  \w     64.00 103.00   0.50    0.81    --  107.75 -95.00 -30.00   78
 14  \w     83.00 108.00   0.50    0.81    --  107.75-107.00  68.32   50
 15  \w     61.00  87.00   0.50    0.81    --  107.75 -88.00 151.88   52
 16  \w    103.00 128.00   0.50    0.81    --  107.75 -88.00 151.88   50
 17  \w     44.00  80.00   0.50    0.81    --  107.75 -87.00-135.98   72
 18  \w     78.00 103.00   0.50    0.81    --  107.75 -77.00 -90.00   50
 19  \w     37.00  69.00   0.50    0.81    --  107.75 -77.00-120.00   64
 20  \w     41.00  66.00   0.50    0.81    --  107.75 -72.00-119.61   50
 21  \w     37.00  69.00   0.50    0.81    --  107.75 -77.00 -90.00   64
 22  \w     39.00  64.00   0.50    0.81    --  107.75 -61.00 -60.00   50
 23  \w     39.00  71.00   0.50    0.81    --  107.75 -61.00 -90.00   64
 24  \w     40.00  65.00   0.50    0.81    --  107.75 -61.00 -30.00   50
 25  \w     40.00  70.00   0.50    0.81    --  107.75 -61.00   0.00   60
 26  \w     36.00  61.00   0.50    0.81    --  107.75 -61.00  60.00   50
 27  \w     45.00  71.00   0.50    0.81    --  107.75 -61.00  90.00   52
 28  \w    -24.00  25.00   0.50    0.20    --   48.45 -19.00-120.00   98
 29  \w    -23.00  42.00   0.50    0.20    --   48.45 -38.00   0.00  130
 30  \w    103.00 147.00   0.50    0.81    --  107.75  61.00 150.00   88
 31  \w    109.00 135.00   0.50    0.81    --  107.75  45.00  90.00   52
 32  \w    106.00 136.00   0.50    0.81    --  107.75  45.00  60.00   60
 33  \w    145.00 177.00   0.50    0.81    --  107.75  45.00  60.00   64
 34  \w    107.00 177.00   0.50    0.81    --  107.75  45.00   0.00  140
 35  \w     99.00 124.00   0.50    0.81    --  107.75  30.00 -60.00   50
 36  \w    143.00 171.00   0.50    0.81    --  107.75  30.00 -60.00   56
 37  \w    148.00 175.00   0.50    0.81    --  107.75  35.00 -90.64   54
 38  \w    130.00 165.00   0.50    0.81    --  107.75  45.00-120.00   70
 39  \w    101.00 126.00   0.50    0.81    --  107.75  45.00-120.00   50
 40  \w    115.00 140.00   0.50    0.81    --  107.75 116.00  -0.00   50
 41  \w     96.00 139.00   0.50    0.81    --  107.75 125.00  90.00   86
 42  \w     98.00 123.00   0.50    0.81    --  107.75 125.00 120.00   50
 43  \w     70.00 113.00   0.50    0.81    --  107.75 165.00 146.00   86
 44  \w    143.00 169.00   0.50    0.81    --  107.75 125.00 120.00   52
 45  \w    146.00 172.00   0.50    0.81    --  107.75 125.00  90.00   52
 46  \w    -24.00   2.00   0.50    0.20    --  -48.45  19.00-150.00   52
 47  \w    -83.00 -19.00   0.50    0.20    --  -48.45 116.00  -0.00  128
 48  \w    -50.00 -15.00   0.50    0.81    --  -86.25  45.00-150.00   70
 49  \w   -119.00 -75.00   0.50    0.20    --  -48.45-125.00 120.00   88
 50  \w   -120.00 -47.00   0.50    0.20    --  -48.45-165.00 123.00  146
 51  \w   -120.00 -74.00   0.50    0.20    --  -48.45-125.00 -30.00   92
 52  \w   -119.00 -91.00   0.50    0.81    --  -86.25-116.00 -88.00   56
 53  \w     81.00 107.00   0.50    0.81    --  107.75-116.00 -88.00   52
 54  \w    -68.00 -37.00   0.50    0.20    --  -48.70 -57.00  30.00   62
 55  \w   -108.00 -82.00   0.50    0.20    --  -48.70 -57.00  30.00   52
 56  \w   -111.00 -75.00   0.50    0.20    --  -48.70-125.00-150.00   72
 57  \w    -23.00  26.00   0.50    0.20    --  -48.70  19.00 -30.00   98
 58  \w    -17.00   9.00   0.50    0.20    --   48.70 -19.00 -90.00   52
 59  \w    -49.00 -14.00   0.50    0.81    --  -86.25  45.00-180.00   70
 60  \w    -63.00 -36.00   0.50    0.81    --  -86.25  61.00  60.00   54
 61  \w     42.00  68.00   0.50    0.81    --  107.75 -61.00 120.00   52
 62  \w     44.00  82.00   0.50    0.81    --  107.75 -77.00 120.00   76
 63  \w     36.00  61.00   0.50    0.81    --  107.75 -56.00 -60.77   50
 64  \w    110.00 136.00   0.50    0.81    --  107.75 125.00 -90.00   52
 65  \w     43.00  69.00   0.50    0.81    --  107.75 -77.00   0.00   52
 66  \w    111.00 137.00   0.50    0.81    --  107.75  45.00 150.00   52
 67  \w    142.00 178.00   0.50    0.81    --  107.75  45.00 150.00   72
 68  \w     81.00 107.00   0.50    0.81    --  107.75-105.00 -32.81   52
 69  \w     62.00 106.00   0.50    0.81    --  107.75-125.00-120.00   88
 70  \w     73.00 108.00   0.50    0.81    --  107.75-109.00-142.50   70
 71  \w     71.00  96.00   0.50    0.81    --  107.75 -95.00   0.00   50
 72  \w     74.00 106.00   0.50    0.81    --  107.75-101.00  75.63   64
 73  \w     53.00 103.00   0.50    0.81    --  107.75-125.00 -60.00  100
 74  \w    104.00 130.00   0.50    0.81    --  107.75  30.00-150.00   52
 75  \w    139.00 165.00   0.50    0.81    --  107.75 125.00 -90.00   52
 76  \w     38.00  64.00   0.50    0.81    --  107.75-105.00 -32.81   52
 77  \w     38.00  64.00   0.50    0.81    --  107.75 -95.00   0.00   52
 78  \w     36.00  61.00   0.50    0.81    --  107.75 -61.00-150.00   50
 79  \w     41.00  67.00   0.50    0.81    --  107.75 -77.00  30.00   52
 80  \w     71.00  97.00   0.50    0.81    --  107.75 -77.00  30.00   52
 81  \w     92.00 151.00   0.50    0.81    --  107.75  77.00-120.00  118
 82  \w    103.00 129.00   0.50    0.81    --  107.75  15.00-150.00   52
 83  \w    138.00 164.00   0.50    0.81    --  107.75  15.00-150.00   52
 84  \w     74.00  99.00   0.50    0.81    --  107.75 -95.00 150.00   50
 85  \w    101.00 136.00   0.50    0.81    --  107.75  31.00-141.81   70
 86  \w     65.00  91.00   0.50    0.81    --  107.75-103.00 -42.87   52
 87  \w    101.00 128.00   0.50    0.81    --  107.75  30.00 150.00   54
 88  \w    153.00 178.00   0.50    0.81    --  107.75  15.00  30.00   50
 89  \w     94.00 119.00   0.50    0.81    --  107.75  61.00   0.00   50
 90  \w     37.00  63.00   0.50    0.81    --  107.75 -95.00  90.00   52
 91  \w     69.00  94.00   0.50    0.81    --  107.75 -77.00 -30.00   50
 92  \w     80.00 105.00   0.50    0.81    --  107.75 -95.00-150.00   50
 93  \w     77.00 110.00   0.50    0.81    --  107.75-125.00  90.00   66
 94  \w     40.00 105.00   0.50    0.81    --  107.75-125.00 150.00  130
 95  \w    152.00 177.00   0.50    0.81    --  107.75  30.00-180.00   50
 96  \w    149.00 174.00   0.50    0.81    --  107.75  15.00 120.00   50
 97  \w    130.00 156.00   0.50    0.81    --  107.75  30.00-120.00   52
 98  \w    128.00 154.00   0.50    0.81    --  107.75  15.00  90.00   52
 99  \w     83.00 108.00   0.50    0.81    --  107.75 -79.00 138.36   50
100  \w     63.00 103.00   0.50    0.81    --  107.75-101.00 127.57   80
;
_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      -0.0690478000
_diffrn_orient_matrix_UB_12      0.0795305000
_diffrn_orient_matrix_UB_13      0.0710003000
_diffrn_orient_matrix_UB_21      -0.1027378000
_diffrn_orient_matrix_UB_22      -0.0793777000
_diffrn_orient_matrix_UB_23      0.0487838000
_diffrn_orient_matrix_UB_31      0.1505244000
_diffrn_orient_matrix_UB_32      -0.0176092000
_diffrn_orient_matrix_UB_33      0.0995033000
_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  0.0457
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24639
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.802
_diffrn_reflns_theta_min         3.777
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.487
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.576
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.57a (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    1.840
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             724
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2321 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         5296
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0310
_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^)+(0.0478P)^2^+0.3294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0827
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                5119
_reflns_number_total             5296
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05332b2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7062208--7062213.cif.'
_cod_database_code               7062208
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     PGV-2022
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.755
_reflns_odcompleteness_completeness 92.33
_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
2.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C3(H3), C5(H5A), C1(H1), C2(H2), C10(H10), C9(H9), C8(H8),
 C7(H7), C12(H12), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
;
_shelx_res_checksum              44495
_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 2.293
_oxdiff_exptl_absorpt_empirical_full_min 0.655