#------------------------------------------------------------------------------
#$Date: 2023-02-20 12:08:30 +0200 (Mon, 20 Feb 2023) $
#$Revision: 280997 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/23/7712309.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_7712309
loop_
_publ_author_name
'Tang, Jie'
'Xiong, Hualin'
'Tang, Yongxing'
'Yang, Hongwei'
'Cheng, Guangbin'
_publ_section_title
;
 The design and synthesis of new advanced energetic materials based on
 pyrazole-triazole backbones.
;
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_paper_doi               10.1039/d3dt00001j
_journal_year                    2023
_chemical_formula_moiety         'C5 H3 N9 O6, 1.5(C4 H8 O2)'
_chemical_formula_sum            'C11 H15 N9 O9'
_chemical_formula_weight         417.32
_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
_audit_creation_date             2018-12-24
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_audit_update_record
;
2023-02-03 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                114.184(3)
_cell_angle_beta                 98.141(3)
_cell_angle_gamma                99.022(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7665(19)
_cell_length_b                   10.158(2)
_cell_length_c                   10.814(2)
_cell_measurement_reflns_used    1545
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.24
_cell_measurement_theta_min      2.26
_cell_volume                     844.7(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9753
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.018
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         2.121
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0440
_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)+(0.0263P)²+0.3524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0916
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2061
_reflns_number_total             2948
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt00001j2.cif
_cod_data_source_block           1
_cod_original_cell_volume        844.6(3)
_cod_database_code               7712309
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H6A(0.037) H6B(0.037) H7A(0.036) H7B(0.036) H8A(0.032) H8B(0.032)
 H9A(0.031) H9B(0.031) H10A(0.034) H10B(0.034) H11A(0.034) H11B(0.034)
 H2(0.025) H4(0.027) H6(0.025)
 Fixed X: H6A(-0.1334) H6B(0.0214) H7A(0.1001) H7B(-0.0759) H8A(1.0097)
 H8B(0.8455) H9A(0.886) H9B(1.0538) H10A(1.0539) H10B(0.8864) H11A(0.8461)
 H11B(1.011)
 Fixed Y: H6A(0.4357) H6B(0.3925) H7A(0.3419) H7B(0.2444) H8A(0.8294)
 H8B(0.7369) H9A(0.9868) H9B(0.9837) H10A(0.8282) H10B(0.7365) H11A(0.5875)
 H11B(0.5799)
 Fixed Z: H6A(0.0949) H6B(0.1507) H7A(-0.0584) H7B(-0.0905) H8A(0.7907)
 H8B(0.679) H9A(0.7238) H9B(0.6813) H10A(0.436) H10B(0.329) H11A(0.444)
 H11B(0.3967)
;
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.968
_shelx_shelxl_version_number     2014/7
_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.
;
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 0.4456(3) 0.8414(3) 0.3234(2) 0.0195(6) Uani 1 1 d . . . . .
C2 C 0.5184(3) 1.0154(3) 0.2746(2) 0.0186(6) Uani 1 1 d . . . . .
C3 C 0.4860(3) 1.2816(3) 0.1313(2) 0.0186(6) Uani 1 1 d . . . . .
C4 C 0.4146(3) 1.1459(3) 0.1266(2) 0.0187(6) Uani 1 1 d . . . . .
C5 C 0.5215(3) 1.1258(3) 0.2208(2) 0.0189(6) Uani 1 1 d . . . . .
C6 C -0.0210(3) 0.4369(3) 0.0910(3) 0.0312(7) Uani 1 1 d . . . . .
H6A H -0.1334 0.4357 0.0949 0.037 Uiso 1 1 calc R U . . .
H6B H 0.0214 0.3925 0.1507 0.037 Uiso 1 1 calc R U . . .
C7 C -0.0113(3) 0.3469(3) -0.0555(3) 0.0303(7) Uani 1 1 d . . . . .
H7A H 0.1001 0.3419 -0.0584 0.036 Uiso 1 1 calc R U . . .
H7B H -0.0759 0.2444 -0.0905 0.036 Uiso 1 1 calc R U . . .
C8 C 0.9541(3) 0.7936(3) 0.6925(2) 0.0263(6) Uani 1 1 d . . . . .
H8A H 1.0097 0.8294 0.7907 0.032 Uiso 1 1 calc R U . . .
H8B H 0.8455 0.7369 0.6790 0.032 Uiso 1 1 calc R U . . .
C9 C 0.9453(3) 0.9234(3) 0.6622(2) 0.0256(6) Uani 1 1 d . . . . .
H9A H 0.8860 0.9868 0.7238 0.031 Uiso 1 1 calc R U . . .
H9B H 1.0538 0.9837 0.6813 0.031 Uiso 1 1 calc R U . . .
C10 C 0.9455(3) 0.7738(3) 0.4265(3) 0.0283(7) Uani 1 1 d . . . . .
H10A H 1.0539 0.8282 0.4360 0.034 Uiso 1 1 calc R U . . .
H10B H 0.8864 0.7365 0.3290 0.034 Uiso 1 1 calc R U . . .
C11 C 0.9546(3) 0.6458(3) 0.4595(2) 0.0287(7) Uani 1 1 d . . . . .
H11A H 0.8461 0.5875 0.4440 0.034 Uiso 1 1 calc R U . . .
H11B H 1.0110 0.5799 0.3967 0.034 Uiso 1 1 calc R U . . .
N1 N 0.6485(2) 1.0189(2) 0.3554(2) 0.0214(5) Uani 1 1 d . . . . .
N2 N 0.5988(2) 0.9040(2) 0.3864(2) 0.0210(5) Uani 1 1 d D . . . .
H2 H 0.670(3) 0.879(3) 0.438(2) 0.025 Uiso 1 1 d D U . . .
N3 N 0.3880(2) 0.9094(2) 0.25238(19) 0.0192(5) Uani 1 1 d . . . . .
N4 N 0.3494(3) 0.7240(2) 0.3290(2) 0.0226(5) Uani 1 1 d D . . . .
H4 H 0.255(2) 0.676(3) 0.267(2) 0.027 Uiso 1 1 d D U . . .
N5 N 0.4016(3) 0.6477(2) 0.3973(2) 0.0282(6) Uani 1 1 d . . . . .
N6 N 0.6449(2) 1.2456(2) 0.2711(2) 0.0212(5) Uani 1 1 d D . . . .
H6 H 0.738(2) 1.257(3) 0.327(2) 0.025 Uiso 1 1 d D U . . .
N7 N 0.6262(2) 1.3424(2) 0.2170(2) 0.0225(5) Uani 1 1 d . . . . .
N8 N 0.4251(2) 1.3522(2) 0.0486(2) 0.0231(5) Uani 1 1 d . . . . .
N9 N 0.2632(3) 1.0508(2) 0.04126(19) 0.0212(5) Uani 1 1 d . . . . .
O1 O 0.3045(2) 0.5368(2) 0.3813(2) 0.0388(5) Uani 1 1 d . . . . .
O2 O 0.5370(2) 0.6939(2) 0.46994(18) 0.0331(5) Uani 1 1 d . . . . .
O3 O 0.4309(2) 1.4848(2) 0.10829(18) 0.0333(5) Uani 1 1 d . . . . .
O4 O 0.3700(2) 1.27219(19) -0.07617(17) 0.0294(5) Uani 1 1 d . . . . .
O5 O 0.1598(2) 1.1118(2) 0.01704(18) 0.0315(5) Uani 1 1 d . . . . .
O6 O 0.2474(2) 0.91634(19) -0.00402(17) 0.0282(5) Uani 1 1 d . . . . .
O7 O 0.0679(2) 0.58772(18) 0.14285(16) 0.0262(4) Uani 1 1 d . . . . .
O8 O 1.0371(2) 0.69817(18) 0.60221(16) 0.0250(4) Uani 1 1 d . . . . .
O9 O 0.8672(2) 0.87329(19) 0.51871(17) 0.0264(4) Uani 1 1 d . . . . .
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 N4 127.7(2) . . ?
N3 C1 N2 111.7(2) . . ?
N3 C1 N4 120.6(2) . . ?
N1 C2 C5 119.2(2) . . ?
N1 C2 N3 115.9(2) . . ?
N3 C2 C5 124.9(2) . . ?
C4 C3 N8 127.2(2) . . ?
N7 C3 C4 112.9(2) . . ?
N7 C3 N8 119.8(2) . . ?
C3 C4 N9 126.4(2) . . ?
C5 C4 C3 104.8(2) . . ?
C5 C4 N9 128.8(2) . . ?
C4 C5 C2 134.0(2) . . ?
N6 C5 C2 120.8(2) . . ?
N6 C5 C4 105.0(2) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
O7 C6 H6A 109.5 . . ?
O7 C6 H6B 109.5 . . ?
O7 C6 C7 110.7(2) . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
O7 C7 C6 110.3(2) 2_565 . ?
O7 C7 H7A 109.6 2_565 . ?
O7 C7 H7B 109.6 2_565 . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
O8 C8 H8A 109.5 . . ?
O8 C8 H8B 109.5 . . ?
O8 C8 C9 110.6(2) . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
O9 C9 C8 110.3(2) . . ?
O9 C9 H9A 109.6 . . ?
O9 C9 H9B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
O9 C10 H10A 109.5 . . ?
O9 C10 H10B 109.5 . . ?
O9 C10 C11 110.7(2) . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
O8 C11 C10 110.3(2) . . ?
O8 C11 H11A 109.6 . . ?
O8 C11 H11B 109.6 . . ?
C2 N1 N2 102.13(19) . . ?
C1 N2 N1 108.9(2) . . ?
C1 N2 H2 131.4(16) . . ?
N1 N2 H2 119.6(16) . . ?
C1 N3 C2 101.41(19) . . ?
C1 N4 H4 120.3(16) . . ?
N5 N4 C1 123.5(2) . . ?
N5 N4 H4 114.0(16) . . ?
O1 N5 N4 115.4(2) . . ?
O2 N5 N4 118.8(2) . . ?
O2 N5 O1 125.7(2) . . ?
C5 N6 H6 124.9(16) . . ?
C5 N6 N7 113.9(2) . . ?
N7 N6 H6 120.8(16) . . ?
C3 N7 N6 103.41(19) . . ?
O3 N8 C3 117.9(2) . . ?
O3 N8 O4 125.4(2) . . ?
O4 N8 C3 116.8(2) . . ?
O5 N9 C4 116.9(2) . . ?
O6 N9 C4 118.1(2) . . ?
O6 N9 O5 125.0(2) . . ?
C7 O7 C6 110.48(18) 2_565 . ?
C8 O8 C11 109.13(19) . . ?
C10 O9 C9 110.95(19) . . ?
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 1.338(3) . ?
C1 N3 1.325(3) . ?
C1 N4 1.377(3) . ?
C2 C5 1.458(3) . ?
C2 N1 1.321(3) . ?
C2 N3 1.359(3) . ?
C3 C4 1.399(3) . ?
C3 N7 1.312(3) . ?
C3 N8 1.453(3) . ?
C4 C5 1.384(3) . ?
C4 N9 1.438(3) . ?
C5 N6 1.351(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.493(4) . ?
C6 O7 1.438(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 O7 1.437(3) 2_565 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.493(3) . ?
C8 O8 1.439(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 O9 1.442(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.493(3) . ?
C10 O9 1.439(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 O8 1.442(3) . ?
N1 N2 1.367(3) . ?
N2 H2 0.909(18) . ?
N4 H4 0.901(18) . ?
N4 N5 1.356(3) . ?
N5 O1 1.233(3) . ?
N5 O2 1.227(3) . ?
N6 H6 0.899(18) . ?
N6 N7 1.353(3) . ?
N8 O3 1.221(3) . ?
N8 O4 1.228(2) . ?
N9 O5 1.231(3) . ?
N9 O6 1.224(3) . ?
O7 C7 1.437(3) 2_565 ?
