#------------------------------------------------------------------------------
#$Date: 2025-07-06 15:32:54 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 300521 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/46/7134631.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_7134631
loop_
_publ_author_name
'Jiang, Xiu’e'
'Fan, Mingren'
'Wang, Ruihui'
'Wang, Yi'
'Zhang, Qinghua'
_publ_section_title
;
 Facile synthesis of bicyclic heat-resistant energetic materials via a
 C--N coupling strategy
;
_journal_issue                   54
_journal_name_full               'Chemical Communications'
_journal_page_first              9924
_journal_page_last               9927
_journal_paper_doi               10.1039/D5CC02076J
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         '2(Cl O4), C5 H10 N10'
_chemical_formula_sum            'C5 H10 Cl2 N10 O8'
_chemical_formula_weight         409.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-01
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-05-28 deposited with the CCDC.	2025-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                92.785(3)
_cell_angle_beta                 90.887(3)
_cell_angle_gamma                103.678(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2784(7)
_cell_length_b                   9.1672(7)
_cell_length_c                   9.3028(7)
_cell_measurement_reflns_used    2212
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.29
_cell_volume                     684.89(9)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_unetI/netI     0.1129
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8963
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.600
_diffrn_reflns_theta_min         2.193
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1315 before and 0.0707 after correction.
The Ratio of minimum to maximum transmission is 0.8014.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.984
_exptl_crystal_description       blok
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0619
_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)+(0.0396P)²+0.9181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1453
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2103
_reflns_number_total             3410
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc02076j2.cif
_cod_data_source_block           jxe_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7134628--7134631.cif.'
_cod_database_code               7134631
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
2. Restrained distances
 O003-O003_$1
 3 with sigma of 0.05
3.a Aromatic/amide H refined with riding coordinates:
 N00B(H00B), N00G(H00G)
3.b X=CH2 refined with riding coordinates:
 N00E(H00A,H00C), N00H(H00D,H00E), N00I(H00F,H00H)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
Cl01 Cl 0.38885(11) 1.00118(10) 0.27988(11) 0.0234(2) Uani 1 1 d . . . . .
Cl02 Cl 0.75819(11) 0.70017(11) 1.00941(11) 0.0230(2) Uani 1 1 d . . . . .
O003 O 0.4242(3) 1.0138(3) 0.1298(3) 0.0304(7) Uani 1 1 d D . . . .
N004 N -0.0135(4) 0.1636(3) 0.3888(3) 0.0192(7) Uani 1 1 d . . . . .
O005 O 0.4654(3) 0.8890(3) 0.3356(3) 0.0332(7) Uani 1 1 d . . . . .
N006 N 0.2140(4) 0.3826(3) 0.5290(3) 0.0196(7) Uani 1 1 d . . . . .
N007 N -0.0728(4) 0.3421(3) 0.2281(3) 0.0203(7) Uani 1 1 d . . . . .
O008 O 0.6349(3) 0.7315(4) 1.1073(3) 0.0358(8) Uani 1 1 d . . . . .
N009 N 0.1242(4) 0.4128(3) 0.4089(3) 0.0190(7) Uani 1 1 d . . . . .
O00A O 0.2128(3) 0.9545(3) 0.2972(4) 0.0371(8) Uani 1 1 d . . . . .
N00B N -0.2027(4) 0.0871(3) 0.1922(4) 0.0211(7) Uani 1 1 d . . . . .
H00B H -0.267108 0.013695 0.138693 0.025 Uiso 1 1 calc R U . . .
O00C O 0.8305(4) 0.5878(3) 1.0686(3) 0.0379(8) Uani 1 1 d . . . . .
O00D O 0.4550(4) 1.1426(3) 0.3544(3) 0.0396(8) Uani 1 1 d . . . . .
N00E N -0.1575(4) -0.0831(3) 0.3525(4) 0.0235(8) Uani 1 1 d . . . . .
H00A H -0.107590 -0.105500 0.429791 0.028 Uiso 1 1 calc R U . . .
H00C H -0.229830 -0.153859 0.302469 0.028 Uiso 1 1 calc R U . . .
O00F O 0.8840(4) 0.8341(3) 0.9968(4) 0.0423(9) Uani 1 1 d . . . . .
N00G N 0.2955(4) 0.6225(4) 0.4738(3) 0.0197(7) Uani 1 1 d . . . . .
H00G H 0.350845 0.717318 0.479890 0.024 Uiso 1 1 calc R U . . .
N00H N -0.2713(4) 0.2625(4) 0.0477(4) 0.0262(8) Uani 1 1 d . . . . .
H00D H -0.259466 0.356174 0.024216 0.031 Uiso 1 1 calc R U . . .
H00E H -0.342969 0.189655 -0.000611 0.031 Uiso 1 1 calc R U . . .
N00I N 0.1194(4) 0.6268(4) 0.2728(4) 0.0224(7) Uani 1 1 d . . . . .
H00F H 0.160473 0.723451 0.263417 0.027 Uiso 1 1 calc R U . . .
H00H H 0.040403 0.576082 0.212834 0.027 Uiso 1 1 calc R U . . .
O00J O 0.6825(4) 0.6443(4) 0.8733(3) 0.0418(8) Uani 1 1 d . . . . .
N00K N 0.4297(4) 0.5376(5) 0.6707(4) 0.0265(8) Uani 1 1 d . . . . .
C00L C -0.1243(4) 0.0550(4) 0.3123(4) 0.0200(8) Uani 1 1 d . . . . .
C00M C 0.1754(4) 0.5589(4) 0.3750(4) 0.0197(8) Uani 1 1 d . . . . .
C00N C 0.0052(4) 0.2982(4) 0.3361(4) 0.0172(8) Uani 1 1 d . . . . .
C00O C -0.1822(4) 0.2313(4) 0.1543(4) 0.0200(8) Uani 1 1 d . . . . .
C00P C 0.3160(4) 0.5124(4) 0.5639(4) 0.0204(8) Uani 1 1 d . . . . .
H00I H 0.422(6) 0.477(6) 0.739(5) 0.045(15) Uiso 1 1 d . . . . .
H00J H 0.485(5) 0.625(5) 0.697(5) 0.033(14) Uiso 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O003 Cl01 O005 108.75(18) . . ?
O00A Cl01 O003 109.71(19) . . ?
O00A Cl01 O005 108.68(18) . . ?
O00D Cl01 O003 109.12(18) . . ?
O00D Cl01 O005 109.86(19) . . ?
O00D Cl01 O00A 110.70(19) . . ?
O00C Cl02 O008 108.41(19) . . ?
O00F Cl02 O008 108.77(19) . . ?
O00F Cl02 O00C 109.27(19) . . ?
O00F Cl02 O00J 111.3(2) . . ?
O00J Cl02 O008 110.26(19) . . ?
O00J Cl02 O00C 108.8(2) . . ?
C00N N004 C00L 113.2(3) . . ?
C00P N006 N009 103.5(3) . . ?
C00N N007 C00O 114.8(3) . . ?
C00M N009 N006 111.3(3) . . ?
C00M N009 C00N 127.8(3) . . ?
C00N N009 N006 120.8(3) . . ?
C00L N00B H00B 119.7 . . ?
C00O N00B H00B 119.7 . . ?
C00O N00B C00L 120.6(3) . . ?
H00A N00E H00C 120.0 . . ?
C00L N00E H00A 120.0 . . ?
C00L N00E H00C 120.0 . . ?
C00M N00G H00G 126.1 . . ?
C00M N00G C00P 107.8(3) . . ?
C00P N00G H00G 126.1 . . ?
H00D N00H H00E 120.0 . . ?
C00O N00H H00D 120.0 . . ?
C00O N00H H00E 120.0 . . ?
H00F N00I H00H 120.0 . . ?
C00M N00I H00F 120.0 . . ?
C00M N00I H00H 120.0 . . ?
C00P N00K H00I 121(3) . . ?
C00P N00K H00J 122(3) . . ?
H00I N00K H00J 112(4) . . ?
N004 C00L N00B 120.8(3) . . ?
N00E C00L N004 120.1(4) . . ?
N00E C00L N00B 119.0(3) . . ?
N00G C00M N009 105.4(3) . . ?
N00I C00M N009 128.4(4) . . ?
N00I C00M N00G 126.2(3) . . ?
N004 C00N N009 114.9(3) . . ?
N007 C00N N004 130.4(4) . . ?
N007 C00N N009 114.7(3) . . ?
N007 C00O N00B 119.9(3) . . ?
N00H C00O N007 120.1(3) . . ?
N00H C00O N00B 120.0(4) . . ?
N006 C00P N00G 112.0(3) . . ?
N006 C00P N00K 125.1(4) . . ?
N00K C00P N00G 122.9(4) . . ?
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
Cl01 O003 1.436(3) . ?
Cl01 O005 1.441(3) . ?
Cl01 O00A 1.433(3) . ?
Cl01 O00D 1.424(3) . ?
Cl02 O008 1.447(3) . ?
Cl02 O00C 1.435(3) . ?
Cl02 O00F 1.421(3) . ?
Cl02 O00J 1.421(3) . ?
N004 C00L 1.348(5) . ?
N004 C00N 1.326(5) . ?
N006 N009 1.406(4) . ?
N006 C00P 1.309(5) . ?
N007 C00N 1.315(5) . ?
N007 C00O 1.342(5) . ?
N009 C00M 1.361(5) . ?
N009 C00N 1.398(5) . ?
N00B H00B 0.8800 . ?
N00B C00L 1.362(5) . ?
N00B C00O 1.357(5) . ?
N00E H00A 0.8800 . ?
N00E H00C 0.8800 . ?
N00E C00L 1.305(5) . ?
N00G H00G 0.8800 . ?
N00G C00M 1.348(5) . ?
N00G C00P 1.382(5) . ?
N00H H00D 0.8800 . ?
N00H H00E 0.8800 . ?
N00H C00O 1.309(5) . ?
N00I H00F 0.8800 . ?
N00I H00H 0.8800 . ?
N00I C00M 1.299(5) . ?
N00K C00P 1.331(5) . ?
N00K H00I 0.86(5) . ?
N00K H00J 0.84(5) . ?
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
N006 N009 C00M N00G -0.8(4) . . . . ?
N006 N009 C00M N00I -178.9(4) . . . . ?
N006 N009 C00N N004 -0.3(5) . . . . ?
N006 N009 C00N N007 178.3(3) . . . . ?
N009 N006 C00P N00G 0.4(4) . . . . ?
N009 N006 C00P N00K -178.2(4) . . . . ?
C00L N004 C00N N007 4.3(6) . . . . ?
C00L N004 C00N N009 -177.4(3) . . . . ?
C00L N00B C00O N007 5.9(5) . . . . ?
C00L N00B C00O N00H -172.9(3) . . . . ?
C00M N009 C00N N004 176.4(3) . . . . ?
C00M N009 C00N N007 -5.0(5) . . . . ?
C00M N00G C00P N006 -0.9(4) . . . . ?
C00M N00G C00P N00K 177.7(4) . . . . ?
C00N N004 C00L N00B 1.2(5) . . . . ?
C00N N004 C00L N00E -179.0(3) . . . . ?
C00N N007 C00O N00B -1.1(5) . . . . ?
C00N N007 C00O N00H 177.7(3) . . . . ?
C00N N009 C00M N00G -177.8(3) . . . . ?
C00N N009 C00M N00I 4.1(6) . . . . ?
C00O N007 C00N N004 -4.3(6) . . . . ?
C00O N007 C00N N009 177.4(3) . . . . ?
C00O N00B C00L N004 -6.0(5) . . . . ?
C00O N00B C00L N00E 174.2(3) . . . . ?
C00P N006 N009 C00M 0.3(4) . . . . ?
C00P N006 N009 C00N 177.5(3) . . . . ?
C00P N00G C00M N009 1.0(4) . . . . ?
C00P N00G C00M N00I 179.2(4) . . . . ?
