Design and Synthesis of Phenylene-Bridged Isoxazole and Tetrazole-1-ol Based Energetic Materials of Low Sensitivity†
Shreeve, Jean'ne M.; Lal, Sohan; Staples, Richard J.; Dalton Transactions  (2023) –; doi:10.1039/D3DT00166K

data_7712385
_publ_section_title
;
 Design and Synthesis of Phenylene-Bridged Isoxazole and Tetrazole-1-ol
 Based Energetic Materials of Low Sensitivity&#x2020;
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT00166K
_journal_year                    2023
_chemical_formula_moiety         'C16 H12 N6 O14'
_chemical_formula_sum            'C16 H12 N6 O14'
_chemical_formula_weight         512.32
_chemical_melting_point          396.5(5)
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-09-12 deposited with the CCDC.	2023-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.9409(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.58035(14)
_cell_length_b                   13.1249(3)
_cell_length_c                   10.13126(18)
_cell_measurement_reflns_used    6507
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3670
_cell_measurement_theta_min      5.5200
_cell_volume                     1002.56(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.958
_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    -27.00   8.00   0.50    0.09    --  -47.19  19.00-180.00   70
  2  \w    -39.00  -5.00   0.50    0.09    --  -47.19  34.00 -62.00   68
  3  \w    -27.00  27.00   0.50    0.09    --  -47.19  19.00  60.00  108
  4  \w     38.00  68.00   0.50    0.09    --   47.19  34.00 -62.00   60
  5  \w     87.00 116.00   0.50    0.09    --   47.19  34.00 -62.00   58
  6  \w     35.00  62.00   0.50    0.09    --   47.19  31.00  95.68   54
  7  \w     58.00  86.00   0.50    0.09    --   47.19  30.00  97.71   56
  8  \w     35.00  62.00   0.50    0.09    --   47.19  30.00 152.38   54
  9  \w     38.00  81.00   0.50    0.09    --   47.19  30.00 167.54   86
 10  \w      6.00  31.00   0.50    0.09    --   47.19 -34.00 140.00   50
 11  \w    131.00 168.00   0.50    0.35    --  106.50 125.00-180.00   74
 12  \w    146.00 177.00   0.50    0.35    --  106.50  77.00-180.00   62
 13  \w    108.00 137.00   0.50    0.35    --  106.50  34.00 -62.00   58
 14  \w     97.00 124.00   0.50    0.35    --  106.50  30.00   0.00   54
 15  \w     95.00 121.00   0.50    0.35    --  106.50  30.00  30.00   52
 16  \w     95.00 167.00   0.50    0.35    --  106.50  30.00 120.00  144
 17  \w    151.00 176.00   0.50    0.35    --  106.50 125.00 120.00   50
 18  \w    153.00 178.00   0.50    0.35    --  106.50  30.00  30.00   50
 19  \w    152.00 177.00   0.50    0.35    --  106.50  30.00   0.00   50
 20  \w     38.00  69.00   0.50    0.35    --  106.50 -61.00-150.00   62
 21  \w     34.00  69.00   0.50    0.35    --  106.50 -61.00-180.00   70
 22  \w     55.00  92.00   0.50    0.35    --  106.50 -77.00-180.00   74
 23  \w     35.00  68.00   0.50    0.35    --  106.50 -61.00 -90.00   66
 24  \w     34.00  68.00   0.50    0.35    --  106.50 -61.00 -30.00   68
 25  \w     38.00  68.00   0.50    0.35    --  106.50 -61.00-120.00   60
 26  \w     34.00  68.00   0.50    0.35    --  106.50 -61.00  90.00   68
 27  \w     35.00  69.00   0.50    0.35    --  106.50 -61.00 120.00   68
 28  \w     40.00  65.00   0.50    0.35    --  106.50 -61.00 150.00   50
 29  \w    -84.00 -36.00   0.50    0.09    --  -47.19 -25.00  23.66   96
 30  \w    -82.00 -36.00   0.50    0.09    --  -47.19 125.00-180.00   92
 31  \w    -72.00 -39.00   0.50    0.09    --  -47.19 -26.00 -32.15   66
 32  \w   -118.00 -89.00   0.50    0.09    --  -47.19 -26.00 -32.15   58
 33  \w    -96.00 -70.00   0.50    0.09    --  -47.19 -34.00 140.00   52
 34  \w    -47.00 -20.00   0.50    0.35    --  -91.75  45.00 120.00   54
 35  \w    -51.00 -20.00   0.50    0.35    --  -91.75  45.00  60.00   62
 36  \w    -48.00 -21.00   0.50    0.35    --  -91.75  45.00  30.00   54
 37  \w   -126.00-100.00   0.50    0.35    --  -91.75 -34.00 140.00   52
 38  \w   -117.00 -91.00   0.50    0.35    --  -91.75 -30.00  60.00   52
 39  \w   -116.00 -89.00   0.50    0.35    --  -91.75 -30.00   0.00   54
 40  \w   -155.00 -89.00   0.50    0.35    --  -91.75 -30.00 -60.00  132
 41  \w   -133.00 -93.00   0.50    0.35    --  -91.75 -30.00 -30.00   80
 42  \w   -160.00-134.00   0.50    0.35    --  -91.75 -29.00   6.82   52
 43  \w   -121.00 -80.00   0.50    0.35    --  -91.75 -28.00 -18.94   82
 44  \w   -106.00 -79.00   0.50    0.35    --  -91.75 -29.00   6.82   54
 45  \w   -106.00 -80.00   0.50    0.35    --  -91.75 -27.00 -35.20   52
 46  \w   -117.00 -83.00   0.50    0.35    --  -91.75 -27.00  25.22   68
 47  \w   -112.00 -79.00   0.50    0.35    --  -91.75 -27.00  37.09   66
 48  \w   -164.00-127.00   0.50    0.35    --  -91.75 -27.00  37.09   74
 49  \w   -164.00-133.00   0.50    0.35    --  -91.75 -30.00  90.00   62
 50  \w   -104.00 -79.00   0.50    0.35    --  -91.75 -26.00  64.25   50
 51  \w   -152.00-125.00   0.50    0.35    --  -91.75 -94.00 -60.00   54
;
_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      -0.1906853000
_diffrn_orient_matrix_UB_12      0.0398417000
_diffrn_orient_matrix_UB_13      0.0034834000
_diffrn_orient_matrix_UB_21      0.0450447000
_diffrn_orient_matrix_UB_22      0.0320968000
_diffrn_orient_matrix_UB_23      0.1458892000
_diffrn_orient_matrix_UB_31      0.0580503000
_diffrn_orient_matrix_UB_32      0.1056122000
_diffrn_orient_matrix_UB_33      -0.0456619000
_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  0.0332
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11142
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.070
_diffrn_reflns_theta_min         5.535
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.345
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.622
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.67a (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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_description       plate
_exptl_crystal_F_000             524
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2018
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0495P)^2^+0.4057P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1831
_reflns_number_total             2018
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt00166k2.cif
_cod_data_source_block           js922a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '396-397' was changed to
'396.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7712385
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H12N6O14
_chemical_oxdiff_usercomment     SOHAN-343
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.745
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O7-N3 \\sim O7B-N3B \\sim O6B-N3B \\sim O6-N3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O7B) = Uanis(O7)
4. Others
 Sof(O5B)=Sof(O6B)=Sof(O7B)=Sof(N3B)=Sof(H5BC)=Sof(H5BD)=1-FVAR(1)
 Sof(O5)=Sof(O6)=Sof(O7)=Sof(N3)=Sof(H5AA)=Sof(H5AB)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5AA,H5AB), C5(H5BC,H5BD)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8)
;
_shelx_res_checksum              8530
_shelx_hkl_checksum              41765
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id SOHAN-343
_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 1.144
_oxdiff_exptl_absorpt_empirical_full_min 0.791