#------------------------------------------------------------------------------
#$Date: 2023-07-14 00:55:01 +0300 (Fri, 14 Jul 2023) $
#$Revision: 285199 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/18/7131882.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_7131882
loop_
_publ_author_name
'Hu, Yong'
'Dong, Wen-Shuai'
'Lu, Zu-Jia'
'Zhang, Han'
'Zhang, Jianguo'
_publ_section_title
;
 Multi-fused heat-resistant nergetic compound constructed by hydrogen
 bonds
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02504G
_journal_year                    2023
_chemical_formula_sum            'C8 H12 Cl2 N12 O12'
_chemical_formula_weight         539.20
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2023-05-23 deposited with the CCDC.	2023-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.693(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4353(9)
_cell_length_b                   17.0537(16)
_cell_length_c                   10.9355(9)
_cell_measurement_reflns_used    1369
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.288
_cell_measurement_theta_min      2.389
_cell_volume                     1942.0(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1022
_diffrn_reflns_av_sigmaI/netI    0.1030
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9375
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.429
_exptl_absorpt_correction_T_max  0.9665
_exptl_absorpt_correction_T_min  0.9079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.844
_exptl_crystal_density_meas      1.844
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3420
_refine_ls_number_restraints     124
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1884
_refine_ls_R_factor_gt           0.1143
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1719P)²+4.2937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2997
_refine_ls_wR_factor_ref         0.3396
_reflns_number_gt                1863
_reflns_number_total             3420
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3cc02504g2.cif
_cod_data_source_block           210819d
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7131882
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.7540(2) 0.48093(13) 0.0345(2) 0.0555(7) Uani 1 1 d DU . .
Cl2 Cl 0.2771(2) 0.19369(14) 0.0586(2) 0.0617(8) Uani 1 1 d DU . .
N1 N 0.8178(7) 0.3803(4) 0.4979(6) 0.0508(18) Uani 1 1 d . . .
H1 H 0.8053 0.4302 0.4945 0.061 Uiso 1 1 calc R . .
N2 N 0.7582(6) 0.3368(4) 0.5808(6) 0.0484(18) Uani 1 1 d . . .
H2 H 0.7759 0.2878 0.5890 0.058 Uiso 1 1 calc R . .
N3 N 0.8998(6) 0.2679(4) 0.4300(6) 0.0430(16) Uani 1 1 d . . .
N4 N 1.0388(7) 0.2699(4) 0.2713(6) 0.0501(18) Uani 1 1 d . . .
H4 H 1.0814 0.2428 0.2214 0.060 Uiso 1 1 calc R . .
N5 N 0.9765(7) 0.1561(4) 0.3561(7) 0.065(2) Uani 1 1 d . . .
H5A H 0.9343 0.1301 0.4076 0.078 Uiso 1 1 calc R . .
H5B H 1.0228 0.1317 0.3061 0.078 Uiso 1 1 calc R . .
N6 N 1.1196(8) 0.3773(5) 0.1864(7) 0.071(2) Uani 1 1 d . . .
H6A H 1.1636 0.3464 0.1433 0.085 Uiso 1 1 calc R . .
H6B H 1.1263 0.4273 0.1780 0.085 Uiso 1 1 calc R . .
N7 N 0.9675(8) 0.4724(4) 0.3427(7) 0.058(2) Uani 1 1 d . . .
N8 N 0.6508(7) 0.4456(4) 0.6286(6) 0.0477(18) Uani 1 1 d . . .
N9 N 0.5031(6) 0.4433(4) 0.7793(6) 0.0491(18) Uani 1 1 d . . .
H9 H 0.4490 0.4697 0.8190 0.059 Uiso 1 1 calc R . .
N10 N 0.5403(8) 0.5549(4) 0.6750(8) 0.074(3) Uani 1 1 d . . .
H10A H 0.5794 0.5808 0.6211 0.088 Uiso 1 1 calc R . .
H10B H 0.4845 0.5779 0.7171 0.088 Uiso 1 1 calc R . .
N11 N 0.4545(7) 0.3381(4) 0.8917(7) 0.062(2) Uani 1 1 d . . .
H11A H 0.4015 0.3672 0.9281 0.074 Uiso 1 1 calc R . .
H11B H 0.4635 0.2896 0.9117 0.074 Uiso 1 1 calc R . .
N12 N 0.6319(7) 0.2471(4) 0.7576(7) 0.0539(19) Uani 1 1 d . . .
O1 O 0.7589(10) 0.4690(7) -0.0926(7) 0.101(4) Uani 0.689(6) 1 d PDU A 1
O2 O 0.6335(8) 0.4555(5) 0.0715(10) 0.077(3) Uani 0.689(6) 1 d PDU A 1
O3 O 0.8513(10) 0.4350(7) 0.0891(11) 0.117(4) Uani 0.689(6) 1 d PDU A 1
O4 O 0.7700(11) 0.5597(5) 0.0611(13) 0.113(4) Uani 0.689(6) 1 d PDU A 1
O5 O 0.2311(11) 0.1699(7) 0.1710(9) 0.082(3) Uani 0.583(6) 1 d PDU B 1
O6 O 0.2573(15) 0.1327(6) -0.0281(11) 0.115(5) Uani 0.583(6) 1 d PDU B 1
O7 O 0.4066(9) 0.2091(11) 0.0702(14) 0.139(6) Uani 0.583(6) 1 d PDU B 1
O8 O 0.2097(14) 0.2591(7) 0.0138(12) 0.120(4) Uani 0.583(6) 1 d PDU B 1
O9 O 1.0456(8) 0.5077(4) 0.2841(6) 0.076(2) Uani 1 1 d . . .
O10 O 0.8927(8) 0.5073(4) 0.4045(7) 0.082(2) Uani 1 1 d . . .
O11 O 0.7079(7) 0.2124(4) 0.6948(6) 0.071(2) Uani 1 1 d . . .
O12 O 0.5789(7) 0.2123(4) 0.8391(6) 0.072(2) Uani 1 1 d . . .
O1' O 0.6908(18) 0.5425(10) -0.0281(16) 0.101(4) Uani 0.311(6) 1 d PD A 2
O2' O 0.7429(18) 0.4110(8) -0.0315(18) 0.077(3) Uani 0.311(6) 1 d PD A 2
O3' O 0.712(2) 0.4716(14) 0.1518(12) 0.117(4) Uani 0.311(6) 1 d PD A 2
O4' O 0.8867(10) 0.5000(12) 0.046(2) 0.113(4) Uani 0.311(6) 1 d PD A 2
O5' O 0.1540(10) 0.1832(10) 0.0946(15) 0.082(3) Uani 0.417(6) 1 d PD B 2
O6' O 0.3364(17) 0.2598(8) 0.1137(16) 0.115(5) Uani 0.417(6) 1 d PD B 2
O7' O 0.3546(15) 0.1277(8) 0.0761(18) 0.139(6) Uani 0.417(6) 1 d PD B 2
O8' O 0.2692(18) 0.2069(12) -0.0706(9) 0.120(4) Uani 0.417(6) 1 d PD B 2
C1 C 0.9704(5) 0.2312(3) 0.3537(5) 0.044(2) Uani 1 1 d G . .
C2 C 1.0433(5) 0.3487(3) 0.2640(4) 0.048(2) Uani 1 1 d G . .
C3 C 0.9690(4) 0.3899(2) 0.3428(4) 0.046(2) Uani 1 1 d G . .
C4 C 0.8944(3) 0.34714(19) 0.4226(3) 0.0417(19) Uani 1 1 d G . .
C5 C 0.5657(6) 0.4807(3) 0.6928(5) 0.050(2) Uani 1 1 d G . .
C6 C 0.5203(5) 0.3672(3) 0.8075(4) 0.046(2) Uani 1 1 d G . .
C7 C 0.6109(4) 0.3270(2) 0.7399(4) 0.044(2) Uani 1 1 d G . .
C8 C 0.6719(3) 0.36990(19) 0.6501(3) 0.0431(19) Uani 1 1 d G . .
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'
Cl Cl 0.1484 0.1585 '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
O4 Cl1 O3 112.5(7) . . ?
O4 Cl1 O3' 87.6(11) . . ?
O3 Cl1 O3' 78.8(10) . . ?
O4 Cl1 O1' 54.5(9) . . ?
O3 Cl1 O1' 161.1(9) . . ?
O3' Cl1 O1' 111.7(9) . . ?
O4 Cl1 O2' 160.9(10) . . ?
O3 Cl1 O2' 76.9(10) . . ?
O3' Cl1 O2' 111.0(9) . . ?
O1' Cl1 O2' 111.7(9) . . ?
O4 Cl1 O1 109.7(7) . . ?
O3 Cl1 O1 105.8(6) . . ?
O3' Cl1 O1 157.8(11) . . ?
O1' Cl1 O1 70.8(9) . . ?
O2' Cl1 O1 51.2(9) . . ?
O4 Cl1 O2 109.6(5) . . ?
O3 Cl1 O2 110.1(6) . . ?
O3' Cl1 O2 50.2(10) . . ?
O1' Cl1 O2 88.3(9) . . ?
O2' Cl1 O2 80.8(8) . . ?
O1 Cl1 O2 109.2(6) . . ?
O4 Cl1 O4' 69.8(9) . . ?
O3 Cl1 O4' 53.7(10) . . ?
O3' Cl1 O4' 108.1(10) . . ?
O1' Cl1 O4' 107.3(9) . . ?
O2' Cl1 O4' 106.8(8) . . ?
O1 Cl1 O4' 91.3(11) . . ?
O2 Cl1 O4' 157.7(11) . . ?
O7 Cl2 O5' 157.9(10) . . ?
O7 Cl2 O8 110.5(8) . . ?
O5' Cl2 O8 75.2(9) . . ?
O7 Cl2 O7' 65.3(9) . . ?
O5' Cl2 O7' 113.6(9) . . ?
O8 Cl2 O7' 166.7(10) . . ?
O7 Cl2 O6' 53.3(9) . . ?
O5' Cl2 O6' 112.0(8) . . ?
O8 Cl2 O6' 72.9(10) . . ?
O7' Cl2 O6' 110.8(9) . . ?
O7 Cl2 O5 111.3(7) . . ?
O5' Cl2 O5 48.5(8) . . ?
O8 Cl2 O5 110.2(7) . . ?
O7' Cl2 O5 82.8(9) . . ?
O6' Cl2 O5 91.3(9) . . ?
O7 Cl2 O6 107.7(8) . . ?
O5' Cl2 O6 89.9(9) . . ?
O8 Cl2 O6 107.8(7) . . ?
O7' Cl2 O6 63.6(9) . . ?
O6' Cl2 O6 157.0(9) . . ?
O5 Cl2 O6 109.3(7) . . ?
O7 Cl2 O8' 93.2(10) . . ?
O5' Cl2 O8' 107.9(8) . . ?
O8 Cl2 O8' 62.0(9) . . ?
O7' Cl2 O8' 105.0(9) . . ?
O6' Cl2 O8' 107.1(9) . . ?
O5 Cl2 O8' 155.3(9) . . ?
O6 Cl2 O8' 57.0(9) . . ?
C4 N1 N2 120.6(6) . . ?
C4 N1 H1 119.7 . . ?
N2 N1 H1 119.7 . . ?
C8 N2 N1 120.2(6) . . ?
C8 N2 H2 119.9 . . ?
N1 N2 H2 119.9 . . ?
C1 N3 C4 117.5(5) . . ?
C2 N4 C1 123.1(6) . . ?
C2 N4 H4 118.5 . . ?
C1 N4 H4 118.5 . . ?
C1 N5 H5A 120.0 . . ?
C1 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C2 N6 H6A 120.0 . . ?
C2 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
O10 N7 O9 121.4(8) . . ?
O10 N7 C3 119.6(7) . . ?
O9 N7 C3 118.9(7) . . ?
C5 N8 C8 117.3(5) . . ?
C5 N9 C6 123.7(6) . . ?
C5 N9 H9 118.1 . . ?
C6 N9 H9 118.1 . . ?
C5 N10 H10A 120.0 . . ?
C5 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C6 N11 H11A 120.0 . . ?
C6 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
O12 N12 O11 120.5(7) . . ?
O12 N12 C7 119.9(6) . . ?
O11 N12 C7 119.6(6) . . ?
N5 C1 N3 119.6(5) . . ?
N5 C1 N4 118.1(5) . . ?
N3 C1 N4 122.3(5) . . ?
N6 C2 N4 116.1(6) . . ?
N6 C2 C3 127.4(4) . . ?
N4 C2 C3 116.5(3) . . ?
C2 C3 N7 120.9(3) . . ?
C2 C3 C4 118.3 . . ?
N7 C3 C4 120.8(3) . . ?
N1 C4 N3 114.7(4) . . ?
N1 C4 C3 123.2(3) . . ?
N3 C4 C3 122.1(3) . . ?
N10 C5 N8 120.0(5) . . ?
N10 C5 N9 117.5(5) . . ?
N8 C5 N9 122.5(5) . . ?
N11 C6 N9 117.9(6) . . ?
N11 C6 C7 126.5(4) . . ?
N9 C6 C7 115.6(3) . . ?
N12 C7 C8 122.1(3) . . ?
N12 C7 C6 120.4(3) . . ?
C8 C7 C6 117.4 . . ?
N8 C8 N2 114.8(5) . . ?
N8 C8 C7 123.4(3) . . ?
N2 C8 C7 121.8(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
Cl1 O4 1.383(7) . ?
Cl1 O3 1.387(8) . ?
Cl1 O3' 1.393(10) . ?
Cl1 O1' 1.395(10) . ?
Cl1 O2' 1.395(9) . ?
Cl1 O1 1.408(7) . ?
Cl1 O2 1.415(7) . ?
Cl1 O4' 1.421(9) . ?
Cl2 O7 1.375(8) . ?
Cl2 O5' 1.380(9) . ?
Cl2 O8 1.391(8) . ?
Cl2 O7' 1.392(9) . ?
Cl2 O6' 1.403(9) . ?
Cl2 O5 1.408(8) . ?
Cl2 O6 1.414(8) . ?
Cl2 O8' 1.427(9) . ?
N1 C4 1.313(7) . ?
N1 N2 1.353(9) . ?
N1 H1 0.8600 . ?
N2 C8 1.338(7) . ?
N2 H2 0.8600 . ?
N3 C1 1.307(7) . ?
N3 C4 1.355(7) . ?
N4 C2 1.347(8) . ?
N4 C1 1.356(7) . ?
N4 H4 0.8600 . ?
N5 C1 1.284(8) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 C2 1.297(8) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 O10 1.220(9) . ?
N7 O9 1.226(9) . ?
N7 C3 1.406(8) . ?
N8 C5 1.311(7) . ?
N8 C8 1.328(7) . ?
N9 C5 1.344(7) . ?
N9 C6 1.344(8) . ?
N9 H9 0.8600 . ?
N10 C5 1.306(8) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N11 C6 1.282(8) . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
N12 O12 1.231(8) . ?
N12 O11 1.232(8) . ?
N12 C7 1.392(8) . ?
C2 C3 1.3872(12) . ?
C3 C4 1.4095(12) . ?
C6 C7 1.4142(12) . ?
C7 C8 1.4095(12) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 N2 C8 -174.3(6) . . . . ?
C4 N3 C1 N5 -178.8(6) . . . . ?
C4 N3 C1 N4 1.5(11) . . . . ?
C2 N4 C1 N5 -177.4(7) . . . . ?
C2 N4 C1 N3 2.3(12) . . . . ?
C1 N4 C2 N6 175.5(7) . . . . ?
C1 N4 C2 C3 -2.7(9) . . . . ?
N6 C2 C3 N7 1.8(7) . . . . ?
N4 C2 C3 N7 179.7(7) . . . . ?
N6 C2 C3 C4 -178.5(6) . . . . ?
N4 C2 C3 C4 -0.6(4) . . . . ?
O10 N7 C3 C2 173.3(7) . . . . ?
O9 N7 C3 C2 -9.6(10) . . . . ?
O10 N7 C3 C4 -6.5(10) . . . . ?
O9 N7 C3 C4 170.6(6) . . . . ?
N2 N1 C4 N3 4.5(9) . . . . ?
N2 N1 C4 C3 -173.5(5) . . . . ?
C1 N3 C4 N1 177.2(6) . . . . ?
C1 N3 C4 C3 -4.8(8) . . . . ?
C2 C3 C4 N1 -177.8(4) . . . . ?
N7 C3 C4 N1 1.9(6) . . . . ?
C2 C3 C4 N3 4.4(4) . . . . ?
N7 C3 C4 N3 -175.9(6) . . . . ?
C8 N8 C5 N10 -179.5(7) . . . . ?
C8 N8 C5 N9 1.5(12) . . . . ?
C6 N9 C5 N10 -179.7(7) . . . . ?
C6 N9 C5 N8 -0.7(12) . . . . ?
C5 N9 C6 N11 -179.8(7) . . . . ?
C5 N9 C6 C7 0.4(9) . . . . ?
O12 N12 C7 C8 178.3(6) . . . . ?
O11 N12 C7 C8 1.4(10) . . . . ?
O12 N12 C7 C6 -5.7(9) . . . . ?
O11 N12 C7 C6 177.5(6) . . . . ?
N11 C6 C7 N12 3.1(6) . . . . ?
N9 C6 C7 N12 -177.0(7) . . . . ?
N11 C6 C7 C8 179.3(6) . . . . ?
N9 C6 C7 C8 -0.8(4) . . . . ?
C5 N8 C8 N2 179.0(6) . . . . ?
C5 N8 C8 C7 -2.0(9) . . . . ?
N1 N2 C8 N8 0.9(9) . . . . ?
N1 N2 C8 C7 -178.0(5) . . . . ?
N12 C7 C8 N8 177.9(7) . . . . ?
C6 C7 C8 N8 1.7(5) . . . . ?
N12 C7 C8 N2 -3.3(6) . . . . ?
C6 C7 C8 N2 -179.4(4) . . . . ?
