An efficient strategy for the preparation of insensitive energetic materials: intramolecular cyclization of picrylhydrazone into an indazole derivative
Tang, Jie; Chen, Jieyi; Yang, Pengju; Yang, Hongwei; Cheng, Guangbin; New Journal of Chemistry 44 (2020) 15849–15856; doi:10.1039/D0NJ03476B

data_7059936
_publ_section_title
;
 An efficient strategy for the preparation of insensitive energetic
 materials: intramolecular cyclization of picrylhydrazone into an indazole
 derivative
;
_journal_issue                   37
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15849
_journal_page_last               15856
_journal_paper_doi               10.1039/D0NJ03476B
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C15 H8 N10 O10'
_chemical_formula_sum            'C15 H8 N10 O10'
_chemical_formula_weight         488.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-14 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.757(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.618(10)
_cell_length_b                   15.497(6)
_cell_length_c                   9.320(3)
_cell_measurement_reflns_used    2291
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.091
_cell_measurement_theta_min      2.594
_cell_volume                     3809(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1106
_diffrn_reflns_av_unetI/netI     0.1223
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11573
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.516
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0986 before and 0.0758 after correction. The Ratio of minimum to maximum transmission is 0.8231. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_description       needle
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.1762
_refine_ls_R_factor_gt           0.1084
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1029P)^2^+46.9454P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2653
_refine_ls_wR_factor_ref         0.3001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1795
_reflns_number_total             3250
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj03476b2.cif
_cod_data_source_block           22019555_0m
_cod_depositor_comments
'Adding full bibliography for 7059934--7059936.cif.'
_cod_database_code               7059936
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.994
_exptl_absorpt_special_details
'Because the crystal size is small and the high Angle has no diffraction point, the Rint and R values are high. After many tests, this data is the best.'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.762(4)
 0.238(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C12(H12), C1(H1), C9(H9), C14(H14)
3.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
;
_olex2_submission_special_instructions 'No special instructions were received'