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_7059935
_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         '2(C3 H7 N O), C16 H8 N14 O12'
_chemical_formula_sum            'C22 H22 N16 O14'
_chemical_formula_weight         734.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                81.816(2)
_cell_angle_beta                 80.771(2)
_cell_angle_gamma                80.036(2)
_cell_formula_units_Z            1
_cell_length_a                   7.8751(4)
_cell_length_b                   8.0958(3)
_cell_length_c                   12.3520(5)
_cell_measurement_reflns_used    3258
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.322
_cell_measurement_theta_min      2.572
_cell_volume                     760.25(6)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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      170.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_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  0.0348
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8624
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.469
_diffrn_reflns_theta_min         2.572
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0661 before and 0.0424 after correction. The Ratio of minimum to maximum transmission is 0.9163. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       block
_exptl_crystal_F_000             378
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.016(3)
_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   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0337P)^2^+0.3059P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2335
_reflns_number_total             3092
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj03476b2.cif
_cod_data_source_block           mo_22020288_0m
_cod_depositor_comments
'Adding full bibliography for 7059934--7059936.cif.'
_cod_database_code               7059935
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O6-N3 \\sim O8-N3
 with sigma of 0.02
3. Others
 Fixed Sof: O8(0.75) O6(0.25)
4.a Aromatic/amide H refined with riding coordinates:
 N5(H5), C1(H1), C10(H10), C7(H7), C5(H5A)
4.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'