#------------------------------------------------------------------------------
#$Date: 2020-03-05 01:31:24 +0200 (Thu, 05 Mar 2020) $
#$Revision: 248801 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/57/7125724.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_7125724
loop_
_publ_author_name
'Chen, Sitong'
'Liu, Yuji'
'Feng, Yongan'
'Yang, Xianjin'
'Zhang, Qinghua'
_publ_section_title
;
 5,6-Fused bicyclic tetrazolo-pyridazine energetic materials.
;
_journal_issue                   10
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1493
_journal_page_last               1496
_journal_paper_doi               10.1039/c9cc08782f
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C4 H2 N8 O4, H2 O'
_chemical_formula_sum            'C4 H4 N8 O5'
_chemical_formula_weight         244.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-08-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-11 deposited with the CCDC.	2020-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.545(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.411(3)
_cell_length_b                   5.0229(5)
_cell_length_c                   15.2453(19)
_cell_measurement_reflns_used    1030
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.851
_cell_measurement_theta_min      2.728
_cell_volume                     1756.4(4)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5703
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.73
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1124 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.8379.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0531P)²+1.9760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1446
_reflns_number_gt                1168
_reflns_number_total             1771
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc08782f2.cif
_cod_data_source_block           22019879qcst3_0m
_cod_depositor_comments
'Adding full bibliography for 7125722--7125725.cif.'
_cod_original_cell_volume        1756.5(4)
_cod_database_code               7125724
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 '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_calc_flag
_atom_site_refinement_flags_posn
O4 O 0.45118(9) 0.7448(4) 0.43219(15) 0.0260(6) Uani 1 d .
O2 O 0.40284(10) 0.3263(5) 0.18268(16) 0.0277(6) Uani 1 d .
O5 O 0.42032(10) 1.1849(5) 0.54232(16) 0.0264(6) Uani 1 d .
H5A H 0.4088 1.2298 0.5911 0.040 Uiso 1 d G
H5B H 0.4582 1.1754 0.5531 0.040 Uiso 1 d G
O1 O 0.41467(11) -0.0636(4) 0.24724(17) 0.0300(6) Uani 1 d .
N5 N 0.27424(11) 0.2291(5) 0.33896(17) 0.0157(6) Uani 1 d .
O3 O 0.47435(10) 0.4079(5) 0.35708(17) 0.0317(7) Uani 1 d .
N8 N 0.23449(11) 0.4732(5) 0.42703(17) 0.0169(6) Uani 1 d .
N1 N 0.34577(12) 0.7624(5) 0.47370(18) 0.0201(6) Uani 1 d .
H1A H 0.3795 0.8450 0.4877 0.024 Uiso 1 calc R
H1B H 0.3168 0.8092 0.4994 0.024 Uiso 1 calc R
N2 N 0.43846(12) 0.5427(5) 0.38555(18) 0.0211(7) Uani 1 d .
N4 N 0.31078(11) 0.1282(5) 0.28850(18) 0.0189(6) Uani 1 d .
N7 N 0.19711(11) 0.2795(5) 0.38799(18) 0.0196(6) Uani 1 d .
N6 N 0.22024(11) 0.1302(5) 0.33431(18) 0.0177(6) Uani 1 d .
N3 N 0.39754(12) 0.1646(5) 0.24008(19) 0.0216(7) Uani 1 d .
C2 C 0.33859(13) 0.5695(6) 0.4145(2) 0.0165(7) Uani 1 d .
C1 C 0.28273(14) 0.4381(6) 0.3954(2) 0.0166(7) Uani 1 d .
C3 C 0.37832(13) 0.4625(6) 0.3654(2) 0.0175(7) Uani 1 d .
C4 C 0.36071(13) 0.2527(6) 0.3046(2) 0.0187(7) Uani 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
H5A O5 H5B 109.4
N6 N5 N4 121.6(2)
C1 N5 N4 128.6(3)
C1 N5 N6 109.8(3)
C1 N8 N7 105.4(2)
H1A N1 H1B 120.0
C2 N1 H1A 120.0
C2 N1 H1B 120.0
O4 N2 C3 117.6(3)
O3 N2 O4 123.5(3)
O3 N2 C3 118.8(3)
C4 N4 N5 110.9(2)
N6 N7 N8 111.9(2)
N7 N6 N5 104.9(2)
O2 N3 C4 115.4(3)
O1 N3 O2 128.0(3)
O1 N3 C4 116.3(3)
N1 C2 C1 117.6(3)
N1 C2 C3 129.7(3)
C3 C2 C1 112.7(3)
N5 C1 C2 119.9(3)
N8 C1 N5 108.0(3)
N8 C1 C2 132.1(3)
C2 C3 N2 120.1(3)
C4 C3 N2 119.7(3)
C4 C3 C2 119.7(3)
N4 C4 N3 110.2(3)
N4 C4 C3 128.0(3)
C3 C4 N3 121.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 N2 1.241(3)
O2 N3 1.218(3)
O5 H5A 0.8701
O5 H5B 0.8705
O1 N3 1.212(3)
N5 N4 1.358(4)
N5 N6 1.347(3)
N5 C1 1.346(4)
O3 N2 1.224(3)
N8 N7 1.363(3)
N8 C1 1.326(4)
N1 H1A 0.8800
N1 H1B 0.8800
N1 C2 1.312(4)
N2 C3 1.437(4)
N4 C4 1.305(4)
N7 N6 1.305(4)
N3 C4 1.499(4)
C2 C1 1.442(4)
C2 C3 1.411(5)
C3 C4 1.410(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
O4 N2 C3 C2 -15.1(4)
O4 N2 C3 C4 172.9(3)
O2 N3 C4 N4 107.3(3)
O2 N3 C4 C3 -66.4(4)
O1 N3 C4 N4 -67.5(3)
O1 N3 C4 C3 118.8(3)
N5 N4 C4 N3 -172.5(2)
N5 N4 C4 C3 0.7(5)
O3 N2 C3 C2 164.0(3)
O3 N2 C3 C4 -8.0(5)
N8 N7 N6 N5 0.3(3)
N1 C2 C1 N5 -176.2(3)
N1 C2 C1 N8 -0.1(5)
N1 C2 C3 N2 8.0(5)
N1 C2 C3 C4 -180.0(3)
N2 C3 C4 N4 168.9(3)
N2 C3 C4 N3 -18.6(4)
N4 N5 N6 N7 -177.4(3)
N4 N5 C1 N8 177.1(3)
N4 N5 C1 C2 -6.0(5)
N7 N8 C1 N5 0.0(3)
N7 N8 C1 C2 -176.4(3)
N6 N5 N4 C4 -179.4(3)
N6 N5 C1 N8 0.1(3)
N6 N5 C1 C2 177.1(3)
C2 C3 C4 N4 -3.1(5)
C2 C3 C4 N3 169.4(3)
C1 N5 N4 C4 4.0(4)
C1 N5 N6 N7 -0.2(3)
C1 N8 N7 N6 -0.2(3)
C1 C2 C3 N2 -170.9(3)
C1 C2 C3 C4 1.1(4)
C3 C2 C1 N5 2.9(4)
C3 C2 C1 N8 179.0(3)
