New green energetic materials based on unsymmetrically substituted pyrazole-tetrazine and hydroperchlorate thereof
Yang, Zhen-Li; Wang, Zhen; Cao, Wenli; Li, Tong; Yang, Junqing; Zhang, Jianguo; New Journal of Chemistry 43 (2019) 18637–18646; doi:10.1039/C9NJ04519H

data_7059008
_publ_section_title
;
 New green energetic materials based on unsymmetrically substituted
 pyrazole-tetrazine and hydroperchlorate thereof
;
_journal_issue                   47
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18637
_journal_page_last               18646
_journal_paper_doi               10.1039/C9NJ04519H
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'Cl O4, C9 H12 N11'
_chemical_formula_sum            'C9 H12 Cl N11 O4'
_chemical_formula_weight         373.75
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-23 deposited with the CCDC.	2019-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                72.190(2)
_cell_angle_beta                 86.574(3)
_cell_angle_gamma                84.812(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2659(9)
_cell_length_b                   9.2453(14)
_cell_length_c                   11.8288(16)
_cell_measurement_reflns_used    935
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.2570
_cell_measurement_theta_min      3.9120
_cell_volume                     752.99(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4158
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.023
_diffrn_reflns_theta_max         66.023
_diffrn_reflns_theta_min         3.927
_exptl_absorpt_coefficient_mu    2.703
_exptl_absorpt_correction_T_max  0.8767
_exptl_absorpt_correction_T_min  0.6565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_description       rod
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         2617
_refine_ls_number_restraints     134
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0533
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0695P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1658
_reflns_number_total             2617
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj04519h1.cif
_cod_data_source_block           170224c
_cod_database_code               7059008
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.877
_shelx_estimated_absorpt_t_min   0.657
_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, All N(H,H) groups
2. Restrained distances
 Cl1-O3 = Cl1-O3' = Cl1-O4 = Cl1-O4' = Cl1-O2 = Cl1-O1' = Cl1-O1 = Cl1-O2'
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim O1 \\sim O2 \\sim O3 \\sim O4 \\sim O1' \\sim O2' \\sim O3' \\sim
O4': within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(Cl1) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O3) \\sim
Ueq, Uanis(O4) \\sim Ueq, Uanis(O1') \\sim Ueq, Uanis(O2') \\sim Ueq,
Uanis(O3') \\sim Ueq, Uanis(O4') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
4. Others
 Sof(O1')=Sof(O2')=Sof(O3')=Sof(O4')=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(O3)=Sof(O4)=FVAR(1)
5.a Riding coordinates:
 N5(H5A,H5B)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4), C2(H2), C6(H6)
5.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'