#------------------------------------------------------------------------------
#$Date: 2020-03-04 12:56:17 +0200 (Wed, 04 Mar 2020) $
#$Revision: 248765 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/36/7703658.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_7703658
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 Na O6'
_chemical_formula_sum            'C4 H2 N5 Na O6'
_chemical_formula_weight         239.10
_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   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc23dfgf
_audit_creation_date             2019-05-24
_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                   7.1249(14)
_cell_length_b                   14.795(3)
_cell_length_c                   15.912(3)
_cell_measurement_reflns_used    2561
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.462
_cell_measurement_theta_min      2.561
_cell_volume                     1677.3(6)
_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      100.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_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  0.0744
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9927
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.560
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0944 before and 0.0672 after correction. The Ratio of minimum to maximum transmission is 0.8207. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0592
_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)+(0.0921P)²+1.2389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1583
_refine_ls_wR_factor_ref         0.1803
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1329
_reflns_number_total             1906
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt04235k2.cif
_cod_data_source_block           22019593_0m
_cod_original_cell_volume        1677.4(6)
_cod_database_code               7703658
_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   0.991
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N5(H5), C3(H3)
;
_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
Na1 Na 0.30889(18) 0.23710(8) 0.57421(8) 0.0135(4) Uani 1 1 d . . . . .
O5 O 0.9132(4) 0.28865(16) 0.60640(16) 0.0216(6) Uani 1 1 d . . . . .
O4 O 0.5805(4) 0.35888(16) 0.55731(16) 0.0224(6) Uani 1 1 d . . . . .
O2 O 0.9148(4) 0.60595(16) 0.62551(16) 0.0234(6) Uani 1 1 d . . . . .
O3 O 0.6725(4) 0.44288(16) 0.45308(16) 0.0246(6) Uani 1 1 d . . . . .
O1 O 0.8460(4) 0.58910(17) 0.49308(16) 0.0246(6) Uani 1 1 d . . . . .
O6 O 0.9021(4) 0.22415(16) 0.72843(17) 0.0280(7) Uani 1 1 d . . . . .
N4 N 0.7766(4) 0.37135(19) 0.79990(19) 0.0172(6) Uani 1 1 d . . . . .
N1 N 0.6665(4) 0.42729(18) 0.53094(19) 0.0178(7) Uani 1 1 d . . . . .
N5 N 0.7191(4) 0.45538(19) 0.81573(19) 0.0186(7) Uani 1 1 d . . . . .
H5 H 0.694929 0.475480 0.866639 0.022 Uiso 1 1 calc R . . . .
N3 N 0.8733(4) 0.28834(19) 0.68129(19) 0.0181(7) Uani 1 1 d . . . . .
N2 N 0.8412(4) 0.56070(19) 0.56732(18) 0.0183(7) Uani 1 1 d . . . . .
C1 C 0.7970(5) 0.3701(2) 0.7166(2) 0.0164(7) Uani 1 1 d . . . . .
C2 C 0.7509(5) 0.4530(2) 0.6781(2) 0.0161(7) Uani 1 1 d . . . . .
C4 C 0.7559(5) 0.4803(2) 0.5901(2) 0.0164(7) Uani 1 1 d . . . . .
C3 C 0.7018(5) 0.5066(2) 0.7460(2) 0.0188(8) Uani 1 1 d . . . . .
H3 H 0.662963 0.567944 0.743858 0.023 Uiso 1 1 calc R . . . .
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'
Na Na 0.0362 0.0249 '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
O5 Na1 O5 115.78(8) 1_455 4_456 ?
O5 Na1 O4 53.56(7) 4_456 4_456 ?
O5 Na1 O4 74.18(7) 1_455 4_456 ?
O5 Na1 O1 81.81(7) 4_456 5_666 ?
O5 Na1 O1 59.38(7) 1_455 5_666 ?
O4 Na1 O5 78.95(8) . 4_456 ?
O4 Na1 O5 122.37(8) . 1_455 ?
O4 Na1 O4 130.07(6) . 4_456 ?
O4 Na1 O2 89.29(9) . 8_755 ?
O4 Na1 O3 149.42(9) . 4_456 ?
O4 Na1 O1 69.53(8) . 5_666 ?
O4 Na1 N4 69.82(9) . 6_557 ?
O2 Na1 O5 90.95(8) 8_755 4_456 ?
O2 Na1 O5 140.69(8) 8_755 1_455 ?
O2 Na1 O4 104.41(8) 8_755 4_456 ?
O2 Na1 O1 158.53(9) 8_755 5_666 ?
O3 Na1 O5 86.72(8) 4_456 1_455 ?
O3 Na1 O5 79.66(8) 4_456 4_456 ?
O3 Na1 O4 43.35(7) 4_456 4_456 ?
O3 Na1 O2 69.47(8) 4_456 8_755 ?
O3 Na1 O1 128.17(9) 4_456 5_666 ?
O1 Na1 O4 87.55(7) 5_666 4_456 ?
N4 Na1 O5 142.11(9) 6_557 4_456 ?
N4 Na1 O5 67.67(8) 6_557 1_455 ?
N4 Na1 O4 141.26(9) 6_557 4_456 ?
N4 Na1 O2 109.11(9) 6_557 8_755 ?
N4 Na1 O3 136.99(9) 6_557 4_456 ?
N4 Na1 O1 67.71(8) 6_557 5_666 ?
Na1 O5 Na1 92.15(7) 1_655 4_556 ?
N3 O5 Na1 112.8(2) . 1_655 ?
N3 O5 Na1 151.2(2) . 4_556 ?
Na1 O4 Na1 98.29(8) . 4_556 ?
N1 O4 Na1 159.3(2) . . ?
N1 O4 Na1 83.34(18) . 4_556 ?
N2 O2 Na1 115.8(2) . 8_765 ?
N1 O3 Na1 89.44(18) . 4_556 ?
N2 O1 Na1 127.9(2) . 5_666 ?
N5 N4 Na1 123.1(2) . 6_657 ?
N5 N4 C1 103.6(3) . . ?
C1 N4 Na1 133.2(2) . 6_657 ?
O4 N1 O3 119.5(3) . . ?
O4 N1 C4 117.1(3) . . ?
O3 N1 C4 123.4(3) . . ?
N4 N5 C3 113.3(3) . . ?
O5 N3 O6 124.0(3) . . ?
O5 N3 C1 117.6(3) . . ?
O6 N3 C1 118.3(3) . . ?
O2 N2 C4 116.6(3) . . ?
O1 N2 O2 120.3(3) . . ?
O1 N2 C4 123.1(3) . . ?
N4 C1 N3 116.1(3) . . ?
N4 C1 C2 113.2(3) . . ?
C2 C1 N3 130.5(3) . . ?
C1 C2 C4 130.7(3) . . ?
C3 C2 C1 102.6(3) . . ?
C3 C2 C4 126.6(3) . . ?
N1 C4 N2 120.8(3) . . ?
N1 C4 C2 119.1(3) . . ?
N2 C4 C2 120.0(3) . . ?
N5 C3 C2 107.3(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
Na1 O5 2.965(3) 1_455 ?
Na1 O5 2.993(3) 4_456 ?
Na1 O4 3.007(3) 4_456 ?
Na1 O4 2.658(3) . ?
Na1 O2 2.882(3) 8_755 ?
Na1 O3 2.868(3) 4_456 ?
Na1 O1 2.996(3) 5_666 ?
Na1 N4 2.830(3) 6_557 ?
O5 N3 1.225(4) . ?
O4 N1 1.255(4) . ?
O2 N2 1.257(4) . ?
O3 N1 1.261(4) . ?
O1 N2 1.254(4) . ?
O6 N3 1.227(4) . ?
N4 N5 1.333(4) . ?
N4 C1 1.334(5) . ?
N1 C4 1.381(4) . ?
N5 C3 1.349(4) . ?
N3 C1 1.440(4) . ?
N2 C4 1.384(4) . ?
C1 C2 1.410(5) . ?
C2 C4 1.458(5) . ?
C2 C3 1.384(5) . ?
