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#$Date: 2024-03-04 21:54:47 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290104 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/26/7132611.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_7132611
loop_
_publ_author_name
'Kumar, Parasar'
'Kumar, Navaneet'
'Ghule, Vikas D.'
'Dharavath, Srinivas'
_publ_section_title
;
 Zwitterionic fused pyrazolo-triazole based high performing energetic
 materials.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1646
_journal_page_last               1649
_journal_paper_doi               10.1039/d3cc05920k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C4 H6 N8 O2'
_chemical_formula_sum            'C4 H6 N8 O2'
_chemical_formula_weight         198.17
_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     iterative
_audit_creation_date             2023-06-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-08-12 deposited with the CCDC.	2024-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 90.00(3)
_cell_angle_gamma                90.00(3)
_cell_formula_units_Z            4
_cell_length_a                   6.744(2)
_cell_length_b                   11.212(2)
_cell_length_c                   9.487(2)
_cell_measurement_reflns_used    3262
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.81
_cell_volume                     717.3(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11348
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.284
_diffrn_reflns_theta_min         2.813
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5930
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1443 before and 0.0625 after correction.
The Ratio of minimum to maximum transmission is 0.7952.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear brownish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 689 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1788
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0377
_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)+(0.0430P)²+0.2947P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0956
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1609
_reflns_number_total             1788
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc05920k2.cif
_cod_data_source_block           30decb_o_0m_a
_cod_depositor_comments          'Adding full bibliography for 7132611.cif.'
_cod_database_code               7132611
_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_max   0.985
_shelx_estimated_absorpt_t_min   0.970
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2.a Rotating group:
 N009(H00A)
2.b Aromatic/amide H refined with riding coordinates:
 N005(H005), N008(H008)
;
_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'
'-x+1/2, y+1/2, z+1/2'
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
O001 O 0.2544(4) 0.67252(19) 0.8323(3) 0.0211(5) Uani 1 1 d . . . . .
O002 O 0.2774(3) 0.86591(18) 0.7935(3) 0.0214(5) Uani 1 1 d . . . . .
N003 N 0.2990(4) 0.7581(2) 0.7540(3) 0.0165(5) Uani 1 1 d . . . . .
N004 N 0.4554(4) 0.7646(2) 0.4018(3) 0.0155(5) Uani 1 1 d . . . . .
N005 N 0.4688(4) 0.9497(2) 0.3556(3) 0.0172(6) Uani 1 1 d . . . . .
H005 H 0.482207 1.017161 0.309143 0.021 Uiso 1 1 calc R U . . .
N006 N 0.4589(4) 0.6395(2) 0.4171(3) 0.0153(5) Uani 1 1 d . . . . .
N007 N 0.4157(4) 0.9445(2) 0.4982(3) 0.0174(5) Uani 1 1 d . . . . .
N008 N 0.3920(4) 0.5191(2) 0.6134(3) 0.0174(5) Uani 1 1 d . . . . .
H008 H 0.335357 0.512375 0.696643 0.021 Uiso 1 1 calc R U . . .
N009 N 0.4684(4) 0.4173(2) 0.5457(3) 0.0197(6) Uani 1 1 d . . . . .
H00A H 0.391853 0.398210 0.476492 0.024 Uiso 1 1 d R U . . .
N00A N 0.5544(4) 0.8173(3) 0.1671(3) 0.0221(6) Uani 1 1 d . . . . .
C1 C 0.4975(4) 0.8423(3) 0.2965(3) 0.0167(6) Uani 1 1 d . . . . .
C4 C 0.4053(4) 0.6269(3) 0.5510(3) 0.0157(6) Uani 1 1 d . . . . .
C2 C 0.4078(4) 0.8287(3) 0.5199(3) 0.0153(6) Uani 1 1 d . . . . .
C3 C 0.3670(4) 0.7396(2) 0.6222(3) 0.0157(6) Uani 1 1 d . . . . .
H00B H 0.595(5) 0.429(3) 0.518(4) 0.022(9) Uiso 1 1 d . . . . .
H00C H 0.573(6) 0.872(4) 0.102(5) 0.030(11) Uiso 1 1 d . . . . .
H00D H 0.551(7) 0.740(5) 0.136(5) 0.049(14) Uiso 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
O001 N003 O002 121.7(3) . . ?
O001 N003 C3 121.0(2) . . ?
O002 N003 C3 117.3(2) . . ?
C1 N004 N006 135.4(3) . . ?
C1 N004 C2 108.4(2) . . ?
C2 N004 N006 116.2(2) . . ?
N007 N005 H005 123.1 . . ?
C1 N005 H005 123.1 . . ?
C1 N005 N007 113.7(3) . . ?
C4 N006 N004 101.5(2) . . ?
C2 N007 N005 101.7(2) . . ?
N009 N008 H008 119.9 . . ?
C4 N008 H008 119.9 . . ?
C4 N008 N009 120.1(3) . . ?
N008 N009 H00A 109.3 . . ?
N008 N009 H00B 111(2) . . ?
H00A N009 H00B 112.7 . . ?
C1 N00A H00C 123(3) . . ?
C1 N00A H00D 120(3) . . ?
H00C N00A H00D 116(4) . . ?
N005 C1 N004 103.8(3) . . ?
N00A C1 N004 127.7(3) . . ?
N00A C1 N005 128.5(3) . . ?
N006 C4 N008 122.2(3) . . ?
N006 C4 C3 113.6(3) . . ?
N008 C4 C3 124.2(3) . . ?
N004 C2 C3 103.6(3) . . ?
N007 C2 N004 112.3(3) . . ?
N007 C2 C3 144.1(3) . . ?
N003 C3 C4 128.7(3) . . ?
N003 C3 C2 126.2(3) . . ?
C2 C3 C4 105.1(3) . . ?
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
O001 N003 1.251(3) . ?
O002 N003 1.274(3) . ?
N003 C3 1.348(4) . ?
N004 N006 1.410(3) . ?
N004 C1 1.355(4) . ?
N004 C2 1.369(4) . ?
N005 H005 0.8800 . ?
N005 N007 1.400(4) . ?
N005 C1 1.343(4) . ?
N006 C4 1.328(4) . ?
N007 C2 1.315(4) . ?
N008 H008 0.8800 . ?
N008 N009 1.407(4) . ?
N008 C4 1.349(4) . ?
N009 H00A 0.8621 . ?
N009 H00B 0.90(4) . ?
N00A C1 1.316(4) . ?
N00A H00C 0.88(5) . ?
N00A H00D 0.92(5) . ?
C4 C3 1.455(4) . ?
C2 C3 1.419(4) . ?
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
O001 N003 C3 C4 -1.9(4) . . . . ?
O001 N003 C3 C2 174.8(3) . . . . ?
O002 N003 C3 C4 179.9(3) . . . . ?
O002 N003 C3 C2 -3.4(4) . . . . ?
N004 N006 C4 N008 -178.8(3) . . . . ?
N004 N006 C4 C3 0.2(3) . . . . ?
N004 C2 C3 N003 -174.9(3) . . . . ?
N004 C2 C3 C4 2.5(3) . . . . ?
N005 N007 C2 N004 1.0(3) . . . . ?
N005 N007 C2 C3 -178.7(4) . . . . ?
N006 N004 C1 N005 -177.9(3) . . . . ?
N006 N004 C1 N00A 1.7(6) . . . . ?
N006 N004 C2 N007 177.5(3) . . . . ?
N006 N004 C2 C3 -2.7(3) . . . . ?
N006 C4 C3 N003 175.5(3) . . . . ?
N006 C4 C3 C2 -1.8(3) . . . . ?
N007 N005 C1 N004 2.1(3) . . . . ?
N007 N005 C1 N00A -177.5(3) . . . . ?
N007 C2 C3 N003 4.9(7) . . . . ?
N007 C2 C3 C4 -177.8(4) . . . . ?
N008 C4 C3 N003 -5.5(5) . . . . ?
N008 C4 C3 C2 177.2(3) . . . . ?
N009 N008 C4 N006 11.3(4) . . . . ?
N009 N008 C4 C3 -167.5(3) . . . . ?
C1 N004 N006 C4 178.0(3) . . . . ?
C1 N004 C2 N007 0.2(4) . . . . ?
C1 N004 C2 C3 180.0(2) . . . . ?
C1 N005 N007 C2 -1.9(3) . . . . ?
C2 N004 N006 C4 1.6(3) . . . . ?
C2 N004 C1 N005 -1.3(3) . . . . ?
C2 N004 C1 N00A 178.3(3) . . . . ?
