#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/21/7122196.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_7122196
loop_
_publ_author_name
'Yang, Xiaoming'
'Lin, Xinyu'
'Yang, Li'
'Zhang, Tonglai'
_publ_section_title
;
 A novel method to synthesize stable nitrogen-rich polynitrobenzenes with
 π-stacking for high-energy-density energetic materials.
;
_journal_issue                   73
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10296
_journal_page_last               10299
_journal_paper_doi               10.1039/c8cc05413d
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C12 H2 Cl2 N8 O14'
_chemical_formula_sum            'C12 H2 Cl2 N8 O14'
_chemical_formula_weight         553.12
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-06-18 deposited with the CCDC.
2018-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.60(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.430(2)
_cell_length_b                   5.4511(11)
_cell_length_c                   15.427(3)
_cell_measurement_reflns_used    2882
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.8019
_cell_volume                     950.4(3)
_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 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153.15
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'multiwire proportional'
_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  0.0386
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6277
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         3.439
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.933
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0978
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0651P)²+2.7743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2058
_refine_ls_wR_factor_ref         0.2146
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1878
_reflns_number_total             2129
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc05413d2.cif
_cod_data_source_block           bwn17090
_cod_depositor_comments
'Adding full bibliography for 7122196--7122197.cif.'
_cod_database_code               7122196
_shelx_shelxl_version_number     2014/7
_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   0.987
_shelx_estimated_absorpt_t_min   0.949
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All O(H) groups
2.a Riding coordinates:
 O7(H7)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Cl1 Cl 0.89612(11) 0.0896(3) 0.26290(8) 0.0463(4) Uani 1 1 d .
O1 O 0.6876(4) -0.5013(8) 0.5291(3) 0.0577(11) Uani 1 1 d .
O2 O 0.8314(4) -0.2719(9) 0.5888(3) 0.0671(13) Uani 1 1 d .
O3 O 0.9076(3) -0.4893(8) 0.4237(3) 0.0570(11) Uani 1 1 d .
O4 O 1.0188(3) -0.1704(9) 0.4196(3) 0.0645(12) Uani 1 1 d .
O5 O 0.7123(5) 0.5532(8) 0.2546(3) 0.0767(16) Uani 1 1 d .
O6 O 0.6012(4) 0.2830(8) 0.1849(2) 0.0637(13) Uani 1 1 d .
N1 N 0.6668(4) 0.3530(7) 0.2482(3) 0.0386(9) Uani 1 1 d .
N2 N 0.9238(3) -0.2685(8) 0.4166(3) 0.0362(9) Uani 1 1 d .
N3 N 0.7528(3) -0.3250(7) 0.5306(2) 0.0349(9) Uani 1 1 d .
N4 N 0.5477(3) -0.0607(7) 0.5061(2) 0.0296(8) Uani 1 1 d .
O7 O 0.5125(3) 0.3032(7) 0.3607(3) 0.0500(10) Uani 1 1 d .
H7 H 0.4661 0.2504 0.3938 0.060 Uiso 1 1 d R
C1 C 0.7980(4) 0.0543(9) 0.3345(3) 0.0317(10) Uani 1 1 d .
C2 C 0.8176(4) -0.1145(8) 0.4045(3) 0.0300(9) Uani 1 1 d .
C3 C 0.7311(4) -0.1493(8) 0.4569(3) 0.0299(9) Uani 1 1 d .
C4 C 0.6257(4) -0.0163(8) 0.4459(3) 0.0286(9) Uani 1 1 d .
C5 C 0.6067(4) 0.1557(8) 0.3767(3) 0.0305(9) Uani 1 1 d .
C6 C 0.6929(4) 0.1817(8) 0.3230(3) 0.0304(9) Uani 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'
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
O5 N1 C6 118.3(4) .
O6 N1 O5 124.2(4) .
O6 N1 C6 117.5(4) .
O3 N2 C2 116.1(4) .
O4 N2 O3 125.5(4) .
O4 N2 C2 118.4(4) .
O1 N3 C3 117.8(4) .
O2 N3 O1 126.2(4) .
O2 N3 C3 115.9(4) .
N4 N4 C4 115.4(5) 3_656
C5 O7 H7 104.2 .
C2 C1 Cl1 121.7(3) .
C6 C1 Cl1 120.5(4) .
C6 C1 C2 117.7(4) .
C1 C2 N2 120.4(4) .
C3 C2 N2 120.0(4) .
C3 C2 C1 119.4(4) .
C2 C3 N3 119.1(4) .
C2 C3 C4 122.5(4) .
C4 C3 N3 118.3(4) .
N4 C4 C5 125.1(4) .
C3 C4 N4 116.9(4) .
C3 C4 C5 118.0(4) .
O7 C5 C4 124.6(4) .
O7 C5 C6 116.9(4) .
C6 C5 C4 118.5(4) .
C1 C6 N1 119.3(4) .
C1 C6 C5 123.7(4) .
C5 C6 N1 116.9(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.699(5) .
O1 N3 1.215(6) .
O2 N3 1.207(5) .
O3 N2 1.225(6) .
O4 N2 1.204(5) .
O5 N1 1.206(6) .
O6 N1 1.201(5) .
N1 C6 1.479(6) .
N2 C2 1.465(5) .
N3 C3 1.478(6) .
N4 N4 1.266(7) 3_656
N4 C4 1.402(6) .
O7 H7 0.8401 .
O7 C5 1.337(5) .
C1 C2 1.411(6) .
C1 C6 1.375(6) .
C2 C3 1.381(6) .
C3 C4 1.395(6) .
C4 C5 1.412(6) .
C5 C6 1.386(6) .
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
Cl1 C1 C2 N2 -0.9(6) .
Cl1 C1 C2 C3 -175.2(3) .
Cl1 C1 C6 N1 -0.9(6) .
Cl1 C1 C6 C5 177.5(4) .
O1 N3 C3 C2 -117.9(5) .
O1 N3 C3 C4 65.1(6) .
O2 N3 C3 C2 65.2(6) .
O2 N3 C3 C4 -111.7(5) .
O3 N2 C2 C1 -128.1(5) .
O3 N2 C2 C3 46.1(6) .
O4 N2 C2 C1 52.6(6) .
O4 N2 C2 C3 -133.1(5) .
O5 N1 C6 C1 -79.3(6) .
O5 N1 C6 C5 102.2(6) .
O6 N1 C6 C1 100.9(5) .
O6 N1 C6 C5 -77.7(6) .
N2 C2 C3 N3 6.2(6) .
N2 C2 C3 C4 -176.9(4) .
N3 C3 C4 N4 -0.1(6) .
N3 C3 C4 C5 178.5(4) .
N4 N4 C4 C3 -179.3(5) 3_656
N4 N4 C4 C5 2.3(7) 3_656
N4 C4 C5 O7 1.5(7) .
N4 C4 C5 C6 179.1(4) .
O7 C5 C6 N1 -5.7(6) .
O7 C5 C6 C1 175.9(4) .
C1 C2 C3 N3 -179.5(4) .
C1 C2 C3 C4 -2.7(7) .
C2 C1 C6 N1 -177.5(4) .
C2 C1 C6 C5 0.9(7) .
C2 C3 C4 N4 -177.0(4) .
C2 C3 C4 C5 1.6(7) .
C3 C4 C5 O7 -176.9(4) .
C3 C4 C5 C6 0.6(6) .
C4 C5 C6 N1 176.6(4) .
C4 C5 C6 C1 -1.9(7) .
C6 C1 C2 N2 175.6(4) .
C6 C1 C2 C3 1.4(6) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189029
