Highly energetic <i>N</i>-cyano-substituted CL-20 analogues: challenging the stability limits of polynitro hexaazaisowurtzitanes.
Parakhin, Vladimir V.; Pokhvisneva, Galina V.; Shlykova, Nina I.; Samigullina, Aida I.; Nikitin, Sergei V.; Smirnov, Gennady A.; Gordeev, Pavel B.; Kon'kova, Tatyana S.; Lempert, David B.; Pivkina, Alla N.; Dalton transactions (Cambridge, England : 2003) 53 (2024) 6100–6111; doi:10.1039/d3dt04203k

data_7715271
_publ_section_title
;
 Highly energetic <i>N</i>-cyano-substituted CL-20 analogues: challenging
 the stability limits of polynitro hexaazaisowurtzitanes.
;
_journal_issue                   13
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6100
_journal_page_last               6111
_journal_paper_doi               10.1039/d3dt04203k
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C7 H6 N12 O10, C2 H3 N'
_chemical_formula_sum            'C9 H9 N13 O10'
_chemical_formula_weight         459.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-10-25
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2023-11-15 deposited with the CCDC.	2024-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.5373(3)
_cell_length_b                   7.8765(2)
_cell_length_c                   32.0668(8)
_cell_measurement_reflns_used    8188
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      78.0520
_cell_measurement_theta_min      2.7790
_cell_volume                     3419.17(14)
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.92a 64-bit (release 05-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_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      99.99(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 0.996
_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   -115.00 -60.00   0.50    1.50    --  -40.74-144.00 161.00  110
  2  \w   -115.00 -62.00   0.50    1.50    --  -40.74-142.00  69.00  106
  3  \w    -31.00  42.00   0.50    1.50    --  -40.74   6.00-121.00  146
  4  \w     37.00 100.00   0.50    1.50    --   40.74-129.00-118.00  126
  5  \w    -43.00  31.00   0.50    1.50    --   40.74  -6.00  61.00  148
  6  \w    -89.00 -23.00   0.50    6.20    --  -98.00 129.00 -45.00  132
  7  \w   -177.00 -16.00   0.50    6.20    --  -98.00  -6.00  61.00  322
  8  \w    -88.00 -23.00   0.50    6.20    --  -98.00 127.00  45.00  130
  9  \w     45.00 113.00   0.50    6.20    --  119.50-127.00 -29.00  136
 10  \w     94.00 178.00   0.50    6.20    --  119.50 127.00  45.00  168
 11  \w     46.00 125.00   0.50    6.20    --  119.50-142.00  69.00  158
 12  \w     38.00 178.00   0.50    6.20    --  119.50   6.00-121.00  280
 13  \w     93.00 178.00   0.50    6.20    --  119.50 129.00 -45.00  170
 14  \w    -43.00  39.00   0.50    1.50    --  -40.74  38.00 -60.00  164
 15  \w      0.00  28.00   0.50    1.50    --   40.74  97.00 128.17   56
 16  \w     44.00 108.00   0.50    6.20    --  119.50-111.00 150.00  128
 17  \w     44.00 108.00   0.50    6.20    --  119.50-111.00  60.00  128
 18  \w     44.00 101.00   0.50    6.20    --  119.50-111.00   0.00  114
 19  \w     74.00 108.00   0.50    6.20    --  119.50-111.00   0.00   68
 20  \w     49.00  93.00   0.50    6.20    --  119.50 -77.00  90.00   88
 21  \w     44.00  97.00   0.50    6.20    --  119.50 -95.00   0.00  106
 22  \w     63.00 116.00   0.50    6.20    --  119.50 178.00 -90.00  106
 23  \w     42.00  68.00   0.50    6.20    --  119.50 -95.00  60.00   52
 24  \w    106.00 149.00   0.50    6.20    --  119.50 111.00  60.00   86
 25  \w     68.00  98.00   0.50    6.20    --  119.50 -95.00 120.00   60
 26  \w     96.00 129.00   0.50    6.20    --  119.50  45.00 -30.00   66
 27  \w    140.00 167.00   0.50    6.20    --  119.50  45.00 -30.00   54
 28  \w    132.00 158.00   0.50    6.20    --  119.50 111.00 150.00   52
 29  \w    118.00 156.00   0.50    6.20    --  119.50 111.00  90.00   76
 30  \w     93.00 118.00   0.50    6.20    --  119.50  77.00 150.00   50
 31  \w     64.00  98.00   0.50    6.20    --  119.50 -77.00  30.00   68
 32  \w    130.00 175.00   0.50    6.20    --  119.50 111.00-180.00   90
 33  \w    133.00 159.00   0.50    6.20    --  119.50 111.00 -30.00   52
 34  \w     42.00  67.00   0.50    6.20    --  119.50 -95.00 -30.00   50
 35  \w     79.00 104.00   0.50    6.20    --  119.50 -95.00 -30.00   50
 36  \w    107.00 177.00   0.50    6.20    --  119.50 111.00-150.00  140
 37  \w     94.00 140.00   0.50    6.20    --  119.50  61.00  30.00   92
 38  \w    144.00 170.00   0.50    6.20    --  119.50  61.00  30.00   52
 39  \w     47.00 108.00   0.50    6.20    --  119.50-111.00-120.00  122
 40  \w     93.00 156.00   0.50    6.20    --  119.50  61.00-150.00  126
 41  \w     90.00 136.00   0.50    6.20    --  119.50  77.00  60.00   92
 42  \w     44.00  78.00   0.50    6.20    --  119.50 -95.00-150.00   68
 43  \w     65.00 108.00   0.50    6.20    --  119.50-111.00 -90.00   86
 44  \w    133.00 167.00   0.50    6.20    --  119.50  77.00-150.00   68
 45  \w     63.00 103.00   0.50    6.20    --  119.50 178.00 -30.00   80
 46  \w    124.00 150.00   0.50    6.20    --  119.50  61.00 150.00   52
 47  \w     98.00 124.00   0.50    6.20    --  119.50  77.00  30.00   52
 48  \w     87.00 117.00   0.50    6.20    --  119.50  77.00 -60.00   60
 49  \w     69.00  95.00   0.50    6.20    --  119.50  15.00  30.00   52
 50  \w     73.00 105.00   0.50    6.20    --  119.50 -77.00 120.00   64
;
_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      0.0077394000
_diffrn_orient_matrix_UB_12      -0.0268322000
_diffrn_orient_matrix_UB_13      -0.0474911000
_diffrn_orient_matrix_UB_21      -0.0044088000
_diffrn_orient_matrix_UB_22      0.1935323000
_diffrn_orient_matrix_UB_23      -0.0067270000
_diffrn_orient_matrix_UB_31      0.1134153000
_diffrn_orient_matrix_UB_32      0.0094327000
_diffrn_orient_matrix_UB_33      0.0029042000
_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  0.0375
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            41607
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.984
_diffrn_reflns_theta_min         2.756
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.428
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.624
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
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    1.784
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_extinction_coef       0.00057(12)
_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   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     592
_refine_ls_number_reflns         7144
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0750P)^2^+6.3400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1509
_refine_ls_wR_factor_ref         0.1511
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.929
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                7081
_reflns_number_total             7144
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt04203k2.cif
_cod_data_source_block           22-PGV-2050
_cod_depositor_comments
'Adding full bibliography for 7715268--7715271.cif.'
_cod_database_code               7715271
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C5H12N10O12
_chemical_oxdiff_usercomment     PGV2050
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.793
_reflns_odcompleteness_completeness 95.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     86.18
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6(4)
 0.4(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C11-C10 \\sim C11A-C10A
 with sigma of 0.02
 N13-C10 \\sim N13A-C10A
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C11) = Uanis(C11A)
Uanis(C10) = Uanis(C10A)
Uanis(N13) = Uanis(N13A)
5. Others
 Sof(N13A)=Sof(C10A)=Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(1)
 Sof(N13)=Sof(C10)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C1B(H1B),
 C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B), C6B(H6B)
6.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C11A(H11D,H11E,H11F)
;
_shelx_res_checksum              86007
_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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.845