Superior thermally robust energetic materials featuring Z-E isomeric bis(3,4-diamino-1,2,4-triazol-5-yl)-1H-pyrazole: self-assembly nitrogen-rich tubes and templates with Hofmeister anions capture architecture
Geng, Wenjing; Jia, Yunfei; Chen, Ya; Ma, Qing; Fan, Guijuan; Liao, Longyu; CrystEngComm  (2020) –; doi:10.1039/D0CE00278J

data_7240273
_publ_section_title
;
 Superior thermally robust energetic materials featuring Z-E isomeric
 bis(3,4-diamino-1,2,4-triazol-5-yl)-1H-pyrazole: self-assembly
 nitrogen-rich tubes and templates with Hofmeister anions capture
 architecture
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00278J
_journal_year                    2020
_chemical_formula_moiety         '6(Cl O4), 6(H2 O), 3(C7 H12 N12)'
_chemical_formula_sum            'C21 H48 Cl6 N36 O30'
_chemical_formula_weight         1497.65
_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     dual
_audit_creation_date             2019-04-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-04 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                66.420(7)
_cell_angle_beta                 78.642(7)
_cell_angle_gamma                69.642(7)
_cell_formula_units_Z            1
_cell_length_a                   10.876(4)
_cell_length_b                   12.218(4)
_cell_length_c                   12.367(5)
_cell_measurement_reflns_used    1557
_cell_measurement_temperature    173
_cell_measurement_theta_max      24.945
_cell_measurement_theta_min      2.602
_cell_volume                     1408.9(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      173
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.1186
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12063
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.801
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.427
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0936 before and 0.0592 after correction. The Ratio of minimum to maximum transmission is 0.7311. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.011
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         6291
_refine_ls_number_restraints     387
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1531
_refine_ls_R_factor_gt           0.0934
_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^)+(0.1978P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2572
_refine_ls_wR_factor_ref         0.3128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3570
_reflns_number_total             6291
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00278j2.cif
_cod_data_source_block           mo_20180058-ma-27_0m
_cod_database_code               7240273
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.923
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 N1A-C14 \\sim N1A-C13
 with sigma of 0.02
 C10-N19 \\sim C10-N16
 with sigma of 0.02
 C11-N15 \\sim C11-N21
 with sigma of 0.02
 N1C-N1B \\sim N1C-N16
 with sigma of 0.02
 N13-N17 \\sim N13-N15
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C8 \\sim N17 \\sim N21 \\sim C11 \\sim N20 \\sim N16 \\sim N19 \\sim N1B \\sim
C13: within 3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N17) \\sim Ueq, Uanis(N21) \\sim Ueq, Uanis(N15) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(C8) \\sim Ueq, Uanis(N17) \\sim Ueq, Uanis(N21) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(N20) \\sim Ueq, Uanis(C13) \\sim Ueq,
Uanis(N16) \\sim Ueq, Uanis(N1B) \\sim Ueq, Uanis(N19) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(O3) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 N13, C8, N17, N21, C9, N15, N14, N18, C11, C12, C10, N20, C13, N19, N1B, C14,
 N16, N1A, N1C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O6, Cl02, O5, O8, O7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl03, O3, O1, O4, O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O6, Cl02, O5, O8, O7, O1, Cl03, O3, O4, O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: N15(0.5) C9(0.5) N21(0.5) N17(0.5) H17(0.5) C8(0.5) N13(0.5)
 H13A(0.5) H13B(0.5) N14(0.5) H14A(0.5) H14B(0.5) N20(0.5) N18(0.5) H18(0.5)
 C11(0.5) C12(0.5) H12(0.5) C10(0.5) C13(0.5) N19(0.5) N1B(0.5) H1BA(0.5)
 C14(0.5) N16(0.5) N1A(0.5) H1AA(0.5) H1AB(0.5) N1C(0.5) H1CA(0.5) H1CB(0.5)
6.a Riding coordinates:
 O14(H14C,H14D), O13(H13C,H13D), O15(H15A,H15B), N11(H11A,H11B), N14(H14A,H14B)
6.b Rotating group:
 N1(H1A,H1B), N13(H13A,H13B), N1A(H1AA,H1AB)
6.c Aromatic/amide H refined with riding coordinates:
 N4(H4), N6(H6), N9(H9), N17(H17), C4(H4A), N18(H18), C12(H12), N1B(H1BA)
6.d Fitted pentagon refined as free rotating group:
 N15(C9,N21,N17,C8), C13(N19,N1B,C14,N16)
6.e X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N12(H12A,H12B), N1C(H1CA,H1CB)
;
_shelx_res_checksum              99103
_olex2_submission_special_instructions 'No special instructions were received'