#------------------------------------------------------------------------------
#$Date: 2023-10-24 00:56:58 +0300 (Tue, 24 Oct 2023) $
#$Revision: 287075 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/22/7132246.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_7132246
loop_
_publ_author_name
'Bhatia, Prachi'
'Pandey, Krishna'
'Das, Priyanka'
'Kumar, Dheeraj'
_publ_section_title
;
 Bis(dinitropyrazolyl)methanes spruced up with hydroxyl group: High
 performance energetic salts with reduced sensitivity
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04445A
_journal_year                    2023
_chemical_formula_moiety         'C7 H4 N8 O10, H2 O'
_chemical_formula_sum            'C7 H6 N8 O11'
_chemical_formula_weight         378.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-09-07 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.195(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9010(6)
_cell_length_b                   7.1701(4)
_cell_length_c                   10.0087(6)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    305(2)
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      2.18
_cell_volume                     671.03(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      305(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0467
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20668
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.503
_diffrn_reflns_theta_min         2.155
_exptl_absorpt_coefficient_mu    0.178
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_description       Block
_exptl_crystal_F_000             384.0
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1161 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.794
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2778
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.794
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.0575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0963
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2642
_reflns_number_total             2788
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04445a2.cif
_cod_data_source_block           dhhfhdhh_0m_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7132246
_shelx_shelxl_version_number     2019/1
_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+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 0.1277(2) -0.1409(3) 0.5434(3) 0.0535(5) Uani 1 1 d . . . . .
O2 O -0.0124(3) -0.0221(4) 0.3499(3) 0.0659(7) Uani 1 1 d . . . . .
O3 O 0.0571(2) 0.3390(3) 0.27154(19) 0.0471(5) Uani 1 1 d . . . . .
H6 H 0.059641 0.447442 0.246434 0.071 Uiso 1 1 calc R U . . .
O4 O 0.2224(3) 0.6735(3) 0.3275(2) 0.0512(5) Uani 1 1 d . . . . .
O5 O 0.4169(2) 0.6759(3) 0.5099(2) 0.0530(5) Uani 1 1 d . . . . .
O6 O 0.1020(3) 0.5281(4) 0.9745(3) 0.0563(6) Uani 1 1 d . . . . .
O7 O 0.1597(3) 0.8126(3) 1.0301(2) 0.0497(5) Uani 1 1 d . . . . .
O8 O 0.36389(19) 0.9900(3) 0.9215(2) 0.0386(4) Uani 1 1 d . . . . .
H3 H 0.282194 1.028718 0.905830 0.058 Uiso 1 1 calc R U . . .
O9 O 0.5796(2) 0.9722(3) 0.7924(3) 0.0576(6) Uani 1 1 d . . . . .
O10 O 0.6610(2) 0.6948(4) 0.7805(3) 0.0534(6) Uani 1 1 d . . . . .
N1 N 0.0913(2) -0.0151(4) 0.4571(2) 0.0412(5) Uani 1 1 d . . . . .
N2 N 0.3043(3) 0.6034(3) 0.4362(2) 0.0381(5) Uani 1 1 d . . . . .
N3 N 0.2807(2) 0.1701(3) 0.6036(2) 0.0334(4) Uani 1 1 d . . . . .
N4 N 0.3380(2) 0.3366(3) 0.59934(19) 0.0309(4) Uani 1 1 d . . . . .
N5 N 0.4099(2) 0.5418(3) 0.8000(2) 0.0298(4) Uani 1 1 d . . . . .
N6 N 0.3038(2) 0.5030(3) 0.8498(2) 0.0324(4) Uani 1 1 d . . . . .
N7 N 0.1707(2) 0.6673(3) 0.9731(2) 0.0360(5) Uani 1 1 d . . . . .
N8 N 0.5702(2) 0.8021(4) 0.7939(2) 0.0366(5) Uani 1 1 d . . . . .
C1 C 0.1738(3) 0.1548(4) 0.4833(2) 0.0344(5) Uani 1 1 d . . . . .
C2 C 0.1557(3) 0.3135(4) 0.3966(2) 0.0349(5) Uani 1 1 d . . . . .
C3 C 0.2651(2) 0.4283(4) 0.4757(2) 0.0332(5) Uani 1 1 d . . . . .
C4 C 0.4559(2) 0.3933(4) 0.7238(2) 0.0333(5) Uani 1 1 d . . . . .
H4 H 0.534791 0.437494 0.695107 0.040 Uiso 1 1 calc R U . . .
H5 H 0.488951 0.286942 0.785832 0.040 Uiso 1 1 calc R U . . .
C5 C 0.2754(2) 0.6629(4) 0.9007(2) 0.0302(5) Uani 1 1 d . . . . .
C6 C 0.3596(2) 0.8132(4) 0.8833(2) 0.0294(5) Uani 1 1 d . . . . .
C7 C 0.4471(2) 0.7258(3) 0.8191(2) 0.0295(5) Uani 1 1 d . . . . .
O11 O 0.1078(3) 0.1436(3) 0.8682(3) 0.0554(6) Uani 1 1 d . . . . .
H7 H 0.099(6) 0.263(9) 0.850(6) 0.095(17) Uiso 1 1 d . . . . .
H8 H 0.071(7) 0.163(12) 0.928(6) 0.11(2) 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
O1 N1 O2 124.2(3) . . ?
O1 N1 C1 118.6(2) . . ?
O2 N1 C1 117.2(3) . . ?
O4 N2 O5 124.1(2) . . ?
O4 N2 C3 116.7(2) . . ?
O5 N2 C3 119.1(2) . . ?
C1 N3 N4 105.5(2) . . ?
N3 N4 C3 110.78(19) . . ?
N3 N4 C4 116.98(19) . . ?
C3 N4 C4 132.1(2) . . ?
N6 N5 C4 117.5(2) . . ?
N6 N5 C7 111.1(2) . . ?
C7 N5 C4 131.1(2) . . ?
C5 N6 N5 104.9(2) . . ?
O6 N7 C5 119.0(2) . . ?
O7 N7 O6 124.5(2) . . ?
O7 N7 C5 116.5(2) . . ?
O9 N8 O10 124.3(2) . . ?
O9 N8 C7 117.1(2) . . ?
O10 N8 C7 118.5(2) . . ?
N3 C1 N1 118.2(2) . . ?
N3 C1 C2 113.4(2) . . ?
C2 C1 N1 128.4(2) . . ?
O3 C2 C1 126.9(3) . . ?
O3 C2 C3 130.9(3) . . ?
C3 C2 C1 102.2(2) . . ?
N4 C3 N2 124.5(2) . . ?
N4 C3 C2 108.1(2) . . ?
C2 C3 N2 127.3(2) . . ?
N4 C4 N5 110.42(18) . . ?
N6 C5 N7 119.4(2) . . ?
N6 C5 C6 114.0(2) . . ?
C6 C5 N7 126.6(2) . . ?
O8 C6 C5 131.5(2) . . ?
O8 C6 C7 127.0(2) . . ?
C7 C6 C5 101.4(2) . . ?
N5 C7 N8 123.4(2) . . ?
N5 C7 C6 108.6(2) . . ?
C6 C7 N8 127.4(2) . . ?
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 1.219(3) . ?
O3 C2 1.322(3) . ?
O4 N2 1.230(3) . ?
O5 N2 1.231(3) . ?
O7 N7 1.210(3) . ?
O8 C6 1.321(3) . ?
O9 N8 1.224(4) . ?
O10 N8 1.224(3) . ?
N1 O2 1.218(3) . ?
N1 C1 1.442(4) . ?
N2 C3 1.408(3) . ?
N3 C1 1.321(3) . ?
N4 N3 1.328(3) . ?
N4 C3 1.378(3) . ?
N4 C4 1.457(3) . ?
N5 C4 1.467(3) . ?
N5 C7 1.366(3) . ?
N6 N5 1.332(3) . ?
N6 C5 1.322(4) . ?
N7 O6 1.211(3) . ?
N7 C5 1.446(3) . ?
N8 C7 1.431(3) . ?
C2 C1 1.406(4) . ?
C3 C2 1.384(4) . ?
C5 C6 1.408(4) . ?
C7 C6 1.387(4) . ?
