#------------------------------------------------------------------------------
#$Date: 2023-11-06 09:24:02 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287336 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/74/7247465.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7247465
loop_
_publ_author_name
'Zhang, Rongzheng'
'Xu, Yuangang'
'Yang, Feng'
'Wang, Pengcheng'
'Lin, Qiuhan'
'Huang, Hui'
'Lu, Ming'
_publ_section_title
;
 Synthesis, characterization and properties of new heat resistant
 energetic materials based on two C--C bridged pyrazole and benzene
 skeletons
;
_journal_issue                   41
_journal_name_full               CrystEngComm
_journal_page_first              5827
_journal_page_last               5833
_journal_paper_doi               10.1039/D3CE00530E
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C12 H4 N10 O12, 2(C H4 O)'
_chemical_formula_sum            'C14 H12 N10 O14'
_chemical_formula_weight         544.34
_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
_audit_block_doi                 10.5517/ccdc.csd.cc2fgrpc
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-08-05 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                103.819(3)
_cell_angle_beta                 90.179(3)
_cell_angle_gamma                95.701(3)
_cell_formula_units_Z            1
_cell_length_a                   6.2299(6)
_cell_length_b                   7.4168(7)
_cell_length_c                   12.7696(12)
_cell_measurement_reflns_used    3367
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.29
_cell_measurement_theta_min      2.84
_cell_volume                     569.90(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8294
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.551
_diffrn_reflns_theta_min         2.843
_diffrn_source.source            'Ius 2.0'
_diffrn_source.type              microfocus
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_description       block
_exptl_crystal_F_000             278
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0503
_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/[σ²(Fo²)+(0.0629P)²+0.1747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1346
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1702
_reflns_number_total             2614
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00530e2.cif
_cod_data_source_block           ZRZ220909_a
_cod_depositor_comments
'Adding full bibliography for 7247464--7247465.cif.'
_cod_database_code               7247465
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.983
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6432(3) 0.8119(3) 0.70410(14) 0.0352(4) Uani 1 1 d . . . . .
C2 C 0.8182(3) 0.7109(2) 0.69466(14) 0.0335(4) Uani 1 1 d . . . . .
C3 C 0.8915(3) 0.7516(3) 0.80243(15) 0.0377(5) Uani 1 1 d . . . . .
C4 C 0.9080(3) 0.5983(2) 0.59601(14) 0.0318(4) Uani 1 1 d . . . . .
C5 C 0.9867(3) 0.6890(2) 0.51869(14) 0.0340(4) Uani 1 1 d . . . . .
H4 H 0.978982 0.816676 0.529539 0.041 Uiso 1 1 calc R U . . .
C6 C 1.0759(3) 0.5931(2) 0.42623(14) 0.0339(4) Uani 1 1 d . . . . .
N1 N 0.7711(3) 0.8621(2) 0.87004(12) 0.0432(4) Uani 1 1 d . . . . .
N2 N 0.6197(3) 0.8984(2) 0.80764(13) 0.0413(4) Uani 1 1 d . . . . .
H2 H 0.519226 0.968371 0.830479 0.050 Uiso 1 1 calc R U . . .
N3 N 0.4960(3) 0.8354(3) 0.62364(14) 0.0470(5) Uani 1 1 d . . . . .
N4 N 1.0770(3) 0.6887(2) 0.84455(14) 0.0477(5) Uani 1 1 d . . . . .
N5 N 1.1618(3) 0.7072(2) 0.35221(13) 0.0463(5) Uani 1 1 d . . . . .
O1 O 0.3584(3) 0.9414(3) 0.65261(14) 0.0690(5) Uani 1 1 d . . . . .
O2 O 0.5171(3) 0.7484(3) 0.53084(13) 0.0694(5) Uani 1 1 d . . . . .
O3 O 1.1045(3) 0.7220(3) 0.94200(13) 0.0747(6) Uani 1 1 d . . . . .
O4 O 1.1977(3) 0.6061(2) 0.77889(13) 0.0621(5) Uani 1 1 d . . . . .
O5 O 1.1135(4) 0.8638(2) 0.36672(14) 0.0779(6) Uani 1 1 d . . . . .
O6 O 1.2782(4) 0.6409(2) 0.28219(15) 0.0896(7) Uani 1 1 d . . . . .
C7 C 0.7158(7) 0.7340(5) 0.1212(3) 0.1145(14) Uani 1 1 d . . . . .
H11 H 0.865939 0.714622 0.118431 0.172 Uiso 1 1 calc R U . . .
H10 H 0.635284 0.635506 0.068990 0.172 Uiso 1 1 calc R U . . .
H7 H 0.664440 0.734031 0.191992 0.172 Uiso 1 1 calc R U . . .
O7 O 0.6890(3) 0.9057(2) 0.09803(13) 0.0669(5) Uani 1 1 d . . . . .
H7A H 0.738012 0.907463 0.038727 0.100 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C2 110.01(17) . . ?
N2 C1 N3 119.62(17) . . ?
C2 C1 N3 130.38(17) . . ?
C1 C2 C3 100.73(16) . . ?
C1 C2 C4 128.85(17) . . ?
C3 C2 C4 130.36(18) . . ?
N1 C3 C2 113.66(18) . . ?
N1 C3 N4 118.95(17) . . ?
C2 C3 N4 127.39(17) . . ?
C5 C4 C6 116.15(16) . 2_766 ?
C5 C4 C2 118.13(15) . . ?
C6 C4 C2 125.71(15) 2_766 . ?
C6 C5 C4 121.02(16) . . ?
C6 C5 H4 119.5 . . ?
C4 C5 H4 119.5 . . ?
C5 C6 C4 122.82(16) . 2_766 ?
C5 C6 N5 115.75(15) . . ?
C4 C6 N5 121.40(15) 2_766 . ?
N2 N1 C3 104.46(15) . . ?
N1 N2 C1 111.12(16) . . ?
N1 N2 H2 124.4 . . ?
C1 N2 H2 124.4 . . ?
O1 N3 O2 124.69(19) . . ?
O1 N3 C1 117.57(17) . . ?
O2 N3 C1 117.74(18) . . ?
O3 N4 O4 124.6(2) . . ?
O3 N4 C3 118.47(18) . . ?
O4 N4 C3 116.94(17) . . ?
O6 N5 O5 123.12(18) . . ?
O6 N5 C6 118.88(17) . . ?
O5 N5 C6 117.99(16) . . ?
O7 C7 H11 109.5 . . ?
O7 C7 H10 109.5 . . ?
H11 C7 H10 109.5 . . ?
O7 C7 H7 109.5 . . ?
H11 C7 H7 109.5 . . ?
H10 C7 H7 109.5 . . ?
C7 O7 H7A 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.340(2) . ?
C1 C2 1.373(3) . ?
C1 N3 1.428(3) . ?
C2 C3 1.401(3) . ?
C2 C4 1.481(2) . ?
C3 N1 1.330(2) . ?
C3 N4 1.437(3) . ?
C4 C5 1.386(2) . ?
C4 C6 1.393(3) 2_766 ?
C5 C6 1.375(2) . ?
C5 H4 0.9300 . ?
C6 N5 1.480(2) . ?
N1 N2 1.321(2) . ?
N2 H2 0.8600 . ?
N3 O1 1.219(2) . ?
N3 O2 1.221(2) . ?
N4 O3 1.217(2) . ?
N4 O4 1.222(2) . ?
N5 O6 1.197(2) . ?
N5 O5 1.201(2) . ?
C7 O7 1.399(3) . ?
C7 H11 0.9600 . ?
C7 H10 0.9600 . ?
C7 H7 0.9600 . ?
O7 H7A 0.8200 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H4 O5 0.93 2.55 3.410(2) 154.9 2_776 yes
N2 H2 O7 0.86 1.80 2.645(2) 168.2 2_676 yes
O7 H7A N1 0.82 2.11 2.904(2) 162.0 1_554 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 C2 C3 -0.8(2) . . . . ?
N3 C1 C2 C3 178.7(2) . . . . ?
N2 C1 C2 C4 -178.23(16) . . . . ?
N3 C1 C2 C4 1.2(3) . . . . ?
C1 C2 C3 N1 1.2(2) . . . . ?
C4 C2 C3 N1 178.59(17) . . . . ?
C1 C2 C3 N4 -178.43(18) . . . . ?
C4 C2 C3 N4 -1.0(3) . . . . ?
C1 C2 C4 C5 62.5(3) . . . . ?
C3 C2 C4 C5 -114.2(2) . . . . ?
C1 C2 C4 C6 -118.4(2) . . . 2_766 ?
C3 C2 C4 C6 64.8(3) . . . 2_766 ?
C6 C4 C5 C6 -0.4(3) 2_766 . . . ?
C2 C4 C5 C6 178.75(17) . . . . ?
C4 C5 C6 C4 0.4(3) . . . 2_766 ?
C4 C5 C6 N5 -177.66(18) . . . . ?
C2 C3 N1 N2 -1.1(2) . . . . ?
N4 C3 N1 N2 178.53(17) . . . . ?
C3 N1 N2 C1 0.6(2) . . . . ?
C2 C1 N2 N1 0.2(2) . . . . ?
N3 C1 N2 N1 -179.36(17) . . . . ?
N2 C1 N3 O1 3.1(3) . . . . ?
C2 C1 N3 O1 -176.3(2) . . . . ?
N2 C1 N3 O2 -177.08(18) . . . . ?
C2 C1 N3 O2 3.5(3) . . . . ?
N1 C3 N4 O3 7.8(3) . . . . ?
C2 C3 N4 O3 -172.6(2) . . . . ?
N1 C3 N4 O4 -171.56(18) . . . . ?
C2 C3 N4 O4 8.1(3) . . . . ?
C5 C6 N5 O6 165.3(2) . . . . ?
C4 C6 N5 O6 -12.7(3) 2_766 . . . ?
C5 C6 N5 O5 -13.5(3) . . . . ?
C4 C6 N5 O5 168.5(2) 2_766 . . . ?
