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#$Date: 2024-02-04 14:25:38 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289603 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/29/7062909.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_7062909
loop_
_publ_author_name
'Shi, Haichuan'
'Wang, Yuqing'
'Wang, Xinyu'
'Zhang, Xiaotian'
'Huang, Ming'
'Yang, Haijun'
'Luo, Zhenghang'
_publ_section_title
;
 Concise synthesis of a fused energetic pyrazolotriazine with good
 performance
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1212
_journal_page_last               1216
_journal_paper_doi               10.1039/D3NJ04391F
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C5 H3 N7 O4, C H4 O'
_chemical_formula_sum            'C6 H7 N7 O5'
_chemical_formula_weight         257.19
_chemical_name_systematic
4-amino-3,8-dinitro-pyrazolo[5,1-c][1,2,4]triazine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-12-02 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5784(8)
_cell_length_b                   26.550(2)
_cell_length_c                   4.5184(5)
_cell_measurement_reflns_used    5815
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      57.017
_cell_measurement_theta_min      6.248
_cell_volume                     1029.10(17)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 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      298.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            8708
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.111
_diffrn_reflns_theta_min         5.341
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1792 before and 0.0511 after correction. The Ratio of minimum to maximum transmission is 0.7907. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1830
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0371
_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)+(0.0456P)²+0.2127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0932
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                1593
_reflns_number_total             1830
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj04391f2.cif
_cod_data_source_block           20221229_2_0m
_cod_depositor_comments
'Adding full bibliography for 7062908--7062909.cif.'
_cod_original_cell_volume        1029.09(17)
_cod_database_code               7062909
_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.
;
_shelx_estimated_absorpt_t_max   0.867
_shelx_estimated_absorpt_t_min   0.841
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.0(6)
 0.0(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Riding coordinates:
 N4(H4A,H4B), O5(H5)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1)
3.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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
O1 O 0.0795(3) -0.19540(7) -0.6170(6) 0.0457(6) Uani 1 1 d . . . . .
O2 O -0.0716(2) -0.16705(7) -0.2675(6) 0.0462(6) Uani 1 1 d . . . . .
O4 O 0.2202(3) -0.44375(8) -0.8684(7) 0.0536(7) Uani 1 1 d . . . . .
O3 O 0.0847(3) -0.47518(8) -0.5083(6) 0.0545(7) Uani 1 1 d . . . . .
N3 N -0.0557(2) -0.33320(7) -0.2868(6) 0.0267(5) Uani 1 1 d . . . . .
N7 N 0.1263(2) -0.30466(8) -0.6528(6) 0.0316(6) Uani 1 1 d . . . . .
N2 N -0.1603(2) -0.31651(8) -0.0792(6) 0.0303(6) Uani 1 1 d . . . . .
N4 N -0.0987(3) -0.41655(8) -0.1737(6) 0.0350(6) Uani 1 1 d . . . . .
H4A H -0.1651 -0.4067 -0.0434 0.042 Uiso 1 1 d R . . . .
H4B H -0.0813 -0.4482 -0.1985 0.042 Uiso 1 1 d R . . . .
N1 N -0.0108(3) -0.20143(8) -0.4063(7) 0.0334(6) Uani 1 1 d . . . . .
N6 N 0.1570(2) -0.35226(9) -0.7069(6) 0.0345(6) Uani 1 1 d . . . . .
N5 N 0.1355(3) -0.43909(8) -0.6526(7) 0.0379(7) Uani 1 1 d . . . . .
C5 C -0.0247(3) -0.38346(9) -0.3328(7) 0.0285(7) Uani 1 1 d . . . . .
C3 C 0.0186(3) -0.29549(9) -0.4403(7) 0.0268(6) Uani 1 1 d . . . . .
C1 C -0.1526(3) -0.26648(10) -0.1044(7) 0.0300(6) Uani 1 1 d . . . . .
H1 H -0.2110 -0.2441 0.0088 0.036 Uiso 1 1 calc R . . . .
C4 C 0.0877(3) -0.38926(10) -0.5579(8) 0.0317(7) Uani 1 1 d . . . . .
C2 C -0.0461(3) -0.25184(9) -0.3214(7) 0.0268(6) Uani 1 1 d . . . . .
O5 O -0.8127(2) -0.09631(7) 1.2623(7) 0.0500(6) Uani 1 1 d . . . . .
H5 H -0.8600 -0.1231 1.2686 0.075 Uiso 1 1 d R . . . .
C6 C -0.9090(4) -0.05721(13) 1.3668(14) 0.0672(13) Uani 1 1 d . . . . .
H6A H -0.8472 -0.0276 1.4013 0.101 Uiso 1 1 calc GR . . . .
H6B H -0.9577 -0.0674 1.5484 0.101 Uiso 1 1 calc GR . . . .
H6C H -0.9877 -0.0499 1.2220 0.101 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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 N3 C5 122.9(2) . . ?
N2 N3 C3 114.4(2) . . ?
C3 N3 C5 122.7(2) . . ?
N6 N7 C3 116.2(2) . . ?
C1 N2 N3 103.3(2) . . ?
H4A N4 H4B 120.1 . . ?
C5 N4 H4A 119.7 . . ?
C5 N4 H4B 120.2 . . ?
O1 N1 C2 117.5(2) . . ?
O2 N1 O1 124.3(2) . . ?
O2 N1 C2 118.2(3) . . ?
N7 N6 C4 121.8(2) . . ?
O4 N5 O3 123.4(2) . . ?
O4 N5 C4 119.7(3) . . ?
O3 N5 C4 116.8(3) . . ?
N3 C5 C4 110.3(2) . . ?
N4 C5 N3 118.5(3) . . ?
N4 C5 C4 131.2(2) . . ?
N3 C3 C2 103.1(2) . . ?
N7 C3 N3 122.9(2) . . ?
N7 C3 C2 134.0(2) . . ?
N2 C1 H1 124.1 . . ?
N2 C1 C2 111.7(2) . . ?
C2 C1 H1 124.1 . . ?
N6 C4 N5 113.5(3) . . ?
N6 C4 C5 126.1(2) . . ?
C5 C4 N5 120.4(3) . . ?
C3 C2 N1 126.4(3) . . ?
C3 C2 C1 107.5(2) . . ?
C1 C2 N1 126.2(2) . . ?
C6 O5 H5 109.8 . . ?
O5 C6 H6A 109.5 . . ?
O5 C6 H6B 109.5 . . ?
O5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
O1 N1 1.238(4) . ?
O2 N1 1.224(3) . ?
O4 N5 1.222(4) . ?
O3 N5 1.238(3) . ?
N3 N2 1.372(3) . ?
N3 C5 1.376(3) . ?
N3 C3 1.374(3) . ?
N7 N6 1.314(3) . ?
N7 C3 1.355(4) . ?
N2 C1 1.335(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8605 . ?
N4 C5 1.301(4) . ?
N1 C2 1.425(3) . ?
N6 C4 1.331(4) . ?
N5 C4 1.450(3) . ?
C5 C4 1.410(4) . ?
C3 C2 1.393(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.395(4) . ?
O5 H5 0.8196 . ?
O5 C6 1.408(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
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
O1 N1 C2 C3 4.3(4) . . . . ?
O1 N1 C2 C1 -175.4(3) . . . . ?
O2 N1 C2 C3 -175.8(3) . . . . ?
O2 N1 C2 C1 4.4(4) . . . . ?
O4 N5 C4 N6 -6.4(4) . . . . ?
O4 N5 C4 C5 172.2(3) . . . . ?
O3 N5 C4 N6 174.6(3) . . . . ?
O3 N5 C4 C5 -6.8(4) . . . . ?
N3 N2 C1 C2 0.0(3) . . . . ?
N3 C5 C4 N6 0.5(4) . . . . ?
N3 C5 C4 N5 -177.9(2) . . . . ?
N3 C3 C2 N1 -179.1(2) . . . . ?
N3 C3 C2 C1 0.6(3) . . . . ?
N7 N6 C4 N5 179.2(2) . . . . ?
N7 N6 C4 C5 0.7(4) . . . . ?
N7 C3 C2 N1 0.4(5) . . . . ?
N7 C3 C2 C1 -179.8(3) . . . . ?
N2 N3 C5 N4 0.5(4) . . . . ?
N2 N3 C5 C4 -179.7(2) . . . . ?
N2 N3 C3 N7 179.7(2) . . . . ?
N2 N3 C3 C2 -0.7(3) . . . . ?
N2 C1 C2 N1 179.4(3) . . . . ?
N2 C1 C2 C3 -0.4(3) . . . . ?
N4 C5 C4 N6 -179.7(3) . . . . ?
N4 C5 C4 N5 1.9(5) . . . . ?
N6 N7 C3 N3 0.0(4) . . . . ?
N6 N7 C3 C2 -179.4(3) . . . . ?
C5 N3 N2 C1 179.0(2) . . . . ?
C5 N3 C3 N7 1.2(4) . . . . ?
C5 N3 C3 C2 -179.2(2) . . . . ?
C3 N3 N2 C1 0.5(3) . . . . ?
C3 N3 C5 N4 178.8(2) . . . . ?
C3 N3 C5 C4 -1.4(4) . . . . ?
C3 N7 N6 C4 -0.9(4) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.0(6)
2 0.0(6)
