#------------------------------------------------------------------------------
#$Date: 2020-03-04 12:56:17 +0200 (Wed, 04 Mar 2020) $
#$Revision: 248765 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/36/7703657.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_7703657
loop_
_publ_author_name
'Lei, Caijin'
'Yang, Hongwei'
'Cheng, Guangbin'
_publ_section_title
;
 New pyrazole energetic materials and their energetic salts: combining the
 dinitromethyl group with nitropyrazole.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1660
_journal_page_last               1667
_journal_paper_doi               10.1039/c9dt04235k
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C4 H2 N5 O6, H4 N'
_chemical_formula_sum            'C4 H6 N6 O6'
_chemical_formula_weight         234.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc23dfdc
_audit_creation_date             2019-05-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-21 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.1753(3)
_cell_length_b                   14.9458(6)
_cell_length_c                   15.9277(6)
_cell_measurement_reflns_used    4684
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.255
_cell_measurement_theta_min      2.725
_cell_volume                     1708.10(12)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0789
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16479
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         2.558
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1393 before and 0.0733 after correction. The Ratio of minimum to maximum transmission is 0.8455. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0461
_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)+(0.0305P)²+1.6694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0998
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1517
_reflns_number_total             1959
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt04235k2.cif
_cod_data_source_block           22019637_0m
_cod_database_code               7703657
_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   0.993
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
O3 O 0.3345(2) 0.44526(9) 0.45307(9) 0.0159(3) Uani 1 1 d . . . . .
O4 O 0.4269(2) 0.36294(9) 0.55712(9) 0.0154(3) Uani 1 1 d . . . . .
O5 O 0.0961(2) 0.28971(9) 0.60439(9) 0.0162(3) Uani 1 1 d . . . . .
O1 O 0.0814(2) 0.60285(9) 0.62505(9) 0.0179(3) Uani 1 1 d . . . . .
O2 O 0.1491(2) 0.58679(9) 0.49287(9) 0.0179(3) Uani 1 1 d . . . . .
O6 O 0.1084(2) 0.22512(10) 0.72600(9) 0.0238(4) Uani 1 1 d . . . . .
N2 N 0.3387(2) 0.42910(11) 0.53046(11) 0.0119(4) Uani 1 1 d . . . . .
N4 N 0.2270(2) 0.37177(11) 0.79830(10) 0.0119(4) Uani 1 1 d . . . . .
N1 N 0.1573(2) 0.55876(11) 0.56668(10) 0.0127(4) Uani 1 1 d . . . . .
N5 N 0.2817(2) 0.45525(12) 0.81479(11) 0.0133(4) Uani 1 1 d . . . . .
N6 N 0.6926(3) 0.23378(13) 0.57682(13) 0.0122(4) Uani 1 1 d . . . . .
N3 N 0.1352(2) 0.28923(11) 0.67957(11) 0.0133(4) Uani 1 1 d . . . . .
C3 C 0.2072(3) 0.37056(13) 0.71570(12) 0.0101(4) Uani 1 1 d . . . . .
C1 C 0.2456(3) 0.48023(13) 0.58965(12) 0.0110(4) Uani 1 1 d . . . . .
C2 C 0.2504(3) 0.45332(13) 0.67732(12) 0.0105(4) Uani 1 1 d . . . . .
C4 C 0.2972(3) 0.50597(13) 0.74556(13) 0.0132(4) Uani 1 1 d . . . . .
H4 H 0.333723 0.567033 0.743766 0.016 Uiso 1 1 calc R . . . .
H6A H 0.790(4) 0.2008(19) 0.5763(17) 0.034(8) Uiso 1 1 d . . . . .
H6B H 0.679(4) 0.2630(17) 0.5296(17) 0.024(7) Uiso 1 1 d . . . . .
H6C H 0.695(4) 0.2721(18) 0.6166(18) 0.031(7) Uiso 1 1 d . . . . .
H6D H 0.596(4) 0.1927(19) 0.5849(17) 0.040(8) Uiso 1 1 d . . . . .
H5 H 0.290(4) 0.4702(17) 0.8646(17) 0.028(7) 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
O3 N2 C1 123.37(16) . . ?
O4 N2 O3 119.87(17) . . ?
O4 N2 C1 116.74(16) . . ?
C3 N4 N5 103.89(16) . . ?
O1 N1 C1 116.46(16) . . ?
O2 N1 O1 119.82(16) . . ?
O2 N1 C1 123.72(17) . . ?
N4 N5 C4 113.00(17) . . ?
N4 N5 H5 117.5(18) . . ?
C4 N5 H5 129.1(18) . . ?
H6A N6 H6B 112(2) . . ?
H6A N6 H6C 112(3) . . ?
H6A N6 H6D 103(2) . . ?
H6B N6 H6C 108(2) . . ?
H6B N6 H6D 111(2) . . ?
H6C N6 H6D 111(2) . . ?
O5 N3 C3 117.77(16) . . ?
O6 N3 O5 123.80(17) . . ?
O6 N3 C3 118.34(16) . . ?
N4 C3 N3 116.56(17) . . ?
N4 C3 C2 113.23(17) . . ?
C2 C3 N3 130.08(17) . . ?
N2 C1 C2 119.32(17) . . ?
N1 C1 N2 120.59(17) . . ?
N1 C1 C2 120.00(17) . . ?
C3 C2 C1 130.70(18) . . ?
C4 C2 C3 102.18(17) . . ?
C4 C2 C1 127.11(18) . . ?
N5 C4 C2 107.71(17) . . ?
N5 C4 H4 126.1 . . ?
C2 C4 H4 126.1 . . ?
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
O3 N2 1.256(2) . ?
O4 N2 1.249(2) . ?
O5 N3 1.230(2) . ?
O1 N1 1.263(2) . ?
O2 N1 1.249(2) . ?
O6 N3 1.226(2) . ?
N2 C1 1.385(3) . ?
N4 N5 1.334(2) . ?
N4 C3 1.323(2) . ?
N1 C1 1.383(2) . ?
N5 C4 1.343(3) . ?
N5 H5 0.83(3) . ?
N6 H6A 0.86(3) . ?
N6 H6B 0.88(3) . ?
N6 H6C 0.85(3) . ?
N6 H6D 0.93(3) . ?
N3 C3 1.441(3) . ?
C3 C2 1.414(3) . ?
C1 C2 1.454(3) . ?
C2 C4 1.383(3) . ?
C4 H4 0.9500 . ?
