#------------------------------------------------------------------------------
#$Date: 2020-03-05 01:31:24 +0200 (Thu, 05 Mar 2020) $
#$Revision: 248801 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/57/7125722.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_7125722
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 Cl2 N4 O2'
_chemical_formula_sum            'C4 H2 Cl2 N4 O2'
_chemical_formula_weight         209.00
_chemical_properties_physical    Deliquescent
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-07-03
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.08.17 svn.r3210 for OlexSys, GUI svn.r5083)
;
_audit_update_record
;
2019-08-14 deposited with the CCDC.	2020-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.450(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.0864(10)
_cell_length_b                   12.7175(8)
_cell_length_c                   7.1186(5)
_cell_measurement_reflns_used    7375
_cell_measurement_temperature    227
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.03
_cell_volume                     1436.55(16)
_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      227.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16870
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.57
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1193 before and 0.0847 after correction.
The Ratio of minimum to maximum transmission is 0.7202.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.933
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0418
_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)+(0.0330P)²+1.1250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                2683
_reflns_number_total             3286
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc08782f2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7125722--7125725.cif.'
_cod_database_code               7125722
_olex2_refinement_description
;
;
_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+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -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
Cl2 Cl 0.08925(3) 0.30079(4) 0.38891(9) 0.03174(17) Uani 1 d
Cl4 Cl 0.58909(3) 0.58845(4) 0.85927(9) 0.02988(16) Uani 1 d
Cl3 Cl 0.29967(4) 0.30970(4) 0.51146(9) 0.03297(17) Uani 1 d
Cl1 Cl -0.19729(4) 0.56776(4) -0.01228(10) 0.03592(18) Uani 1 d
O1 O -0.27936(10) 0.36731(13) 0.0579(2) 0.0307(4) Uani 1 d
O2 O -0.21125(10) 0.24962(12) -0.0761(2) 0.0294(4) Uani 1 d
N2 N -0.06679(13) 0.20616(14) 0.1826(3) 0.0245(4) Uani 1 d
N7 N 0.51160(12) 0.41453(14) 0.7711(3) 0.0255(4) Uani 1 d
N3 N 0.01242(12) 0.47147(14) 0.2709(3) 0.0258(4) Uani 1 d
C7 C 0.42909(14) 0.57179(16) 0.6729(3) 0.0206(4) Uani 1 d
O3 O 0.21876(10) 0.51982(14) 0.5407(3) 0.0391(5) Uani 1 d
C4 C 0.00489(13) 0.36958(16) 0.2701(3) 0.0212(4) Uani 1 d
C8 C 0.50273(13) 0.51635(17) 0.7604(3) 0.0208(4) Uani 1 d
N8 N 0.44730(12) 0.35076(14) 0.6941(3) 0.0261(4) Uani 1 d
C3 C -0.06693(13) 0.31117(15) 0.1815(3) 0.0193(4) Uani 1 d
C5 C 0.37654(14) 0.39551(16) 0.6130(3) 0.0217(5) Uani 1 d
N4 N -0.05124(12) 0.53187(14) 0.1801(3) 0.0262(4) Uani 1 d
N6 N 0.42674(15) 0.67650(15) 0.6686(3) 0.0312(5) Uani 1 d
C1 C -0.12154(14) 0.48516(16) 0.1034(3) 0.0218(5) Uani 1 d
N5 N 0.28558(12) 0.54672(14) 0.4952(3) 0.0258(4) Uani 1 d
C2 C -0.13360(13) 0.37605(16) 0.1037(3) 0.0189(4) Uani 1 d
C6 C 0.36417(13) 0.50384(16) 0.5985(3) 0.0198(4) Uani 1 d
O4 O 0.29238(12) 0.60897(15) 0.3673(3) 0.0425(5) Uani 1 d
N1 N -0.21435(11) 0.32898(13) 0.0225(3) 0.0212(4) Uani 1 d
H2A H -0.0235(18) 0.173(2) 0.240(4) 0.030(7) Uiso 1 d
H6A H 0.3865(19) 0.705(2) 0.613(4) 0.034(8) Uiso 1 d
H2B H -0.1099(19) 0.173(2) 0.129(4) 0.038(8) Uiso 1 d
H6B H 0.4711(19) 0.711(2) 0.722(4) 0.038(8) Uiso 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'
Cl Cl 0.1484 0.1585 '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
C3 N2 H2A 119.3(17)
C3 N2 H2B 119.4(19)
H2A N2 H2B 121(3)
C8 N7 N8 120.06(18)
C4 N3 N4 119.96(18)
N6 C7 C8 121.4(2)
N6 C7 C6 126.5(2)
C6 C7 C8 112.07(18)
N3 C4 Cl2 116.09(16)
N3 C4 C3 125.95(19)
C3 C4 Cl2 117.96(15)
N7 C8 Cl4 115.67(16)
N7 C8 C7 126.16(19)
C7 C8 Cl4 118.16(16)
C5 N8 N7 117.72(17)
N2 C3 C4 121.09(19)
N2 C3 C2 126.5(2)
C2 C3 C4 112.39(17)
N8 C5 Cl3 114.86(16)
N8 C5 C6 124.19(19)
C6 C5 Cl3 120.86(16)
C1 N4 N3 118.22(17)
C7 N6 H6A 119(2)
C7 N6 H6B 118.3(19)
H6A N6 H6B 123(3)
N4 C1 Cl1 114.71(15)
N4 C1 C2 123.85(19)
C2 C1 Cl1 121.33(16)
O3 N5 C6 119.26(19)
O3 N5 O4 124.6(2)
O4 N5 C6 116.12(19)
C3 C2 C1 119.28(19)
C3 C2 N1 119.40(18)
C1 C2 N1 121.31(18)
C7 C6 C5 119.79(19)
C7 C6 N5 119.56(18)
C5 C6 N5 120.53(18)
O1 N1 O2 124.13(18)
O1 N1 C2 119.51(17)
O2 N1 C2 116.33(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl2 C4 1.716(2)
Cl4 C8 1.716(2)
Cl3 C5 1.717(2)
Cl1 C1 1.714(2)
O1 N1 1.217(2)
O2 N1 1.235(2)
N2 C3 1.335(3)
N2 H2A 0.86(3)
N2 H2B 0.85(3)
N7 C8 1.304(3)
N7 N8 1.357(2)
N3 C4 1.301(3)
N3 N4 1.356(2)
C7 C8 1.431(3)
C7 N6 1.332(3)
C7 C6 1.391(3)
O3 N5 1.221(3)
C4 C3 1.430(3)
N8 C5 1.318(3)
C3 C2 1.394(3)
C5 C6 1.393(3)
N4 C1 1.314(3)
N6 H6A 0.79(3)
N6 H6B 0.87(3)
C1 C2 1.401(3)
N5 C6 1.460(3)
N5 O4 1.225(3)
C2 N1 1.461(3)
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
Cl2 C4 C3 N2 -3.4(3)
Cl2 C4 C3 C2 174.99(16)
Cl3 C5 C6 C7 -176.47(17)
Cl3 C5 C6 N5 -0.5(3)
Cl1 C1 C2 C3 172.99(17)
Cl1 C1 C2 N1 -6.4(3)
N2 C3 C2 C1 -175.8(2)
N2 C3 C2 N1 3.6(3)
N7 N8 C5 Cl3 177.75(16)
N7 N8 C5 C6 1.2(3)
N3 C4 C3 N2 177.2(2)
N3 C4 C3 C2 -4.4(3)
N3 N4 C1 Cl1 -178.68(16)
N3 N4 C1 C2 -2.5(3)
O3 N5 C6 C7 -128.3(2)
O3 N5 C6 C5 55.7(3)
C4 N3 N4 C1 4.3(3)
C4 C3 C2 C1 5.9(3)
C4 C3 C2 N1 -174.66(19)
C8 N7 N8 C5 -1.2(3)
C8 C7 C6 C5 -0.8(3)
C8 C7 C6 N5 -176.89(19)
N8 N7 C8 Cl4 -178.86(16)
N8 N7 C8 C7 0.3(4)
N8 C5 C6 C7 -0.1(4)
N8 C5 C6 N5 175.9(2)
C3 C2 N1 O1 135.9(2)
C3 C2 N1 O2 -42.5(3)
N4 N3 C4 Cl2 179.88(17)
N4 N3 C4 C3 -0.8(4)
N4 C1 C2 C3 -3.0(4)
N4 C1 C2 N1 177.6(2)
N6 C7 C8 Cl4 -0.5(3)
N6 C7 C8 N7 -179.6(2)
N6 C7 C6 C5 179.5(2)
N6 C7 C6 N5 3.5(4)
C1 C2 N1 O1 -44.7(3)
C1 C2 N1 O2 136.9(2)
C6 C7 C8 Cl4 179.88(16)
C6 C7 C8 N7 0.8(3)
O4 N5 C6 C7 51.2(3)
O4 N5 C6 C5 -124.8(2)
