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#$Date: 2026-02-19 03:08:52 +0100 (Thu 19 de Feb de 2026) $
#$Revision: 304534 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/09/7160987.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_7160987
loop_
_publ_author_name
'Miao, Xiangyan'
'Yu, Jiyuan'
'Li, Yuchuan'
'Pang, Siping'
_publ_section_title
;
 One-step amino-to-nitro transformation of carbonyl-containing fused-ring
 energetic compounds in nitric acid.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1481
_journal_page_last               1487
_journal_paper_doi               10.1039/d5ob01855b
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'Cl O4, C5 H6 N9 O'
_chemical_formula_sum            'C5 H6 Cl N9 O5'
_chemical_formula_weight         307.64
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-12-11
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-12-11 deposited with the CCDC.	2026-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8115(3)
_cell_length_b                   10.1175(5)
_cell_length_c                   13.4986(5)
_cell_measurement_reflns_used    3341
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.11
_cell_measurement_theta_min      2.51
_cell_volume                     1066.83(8)
_computing_cell_refinement       '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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8345
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.347
_diffrn_reflns_theta_min         2.516
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.404
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1232 before and 0.0812 after correction.
The Ratio of minimum to maximum transmission is 0.7918.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 677 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2168
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0208P)²+0.7217P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0956
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1869
_reflns_number_total             2168
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob01855b2.cif
_cod_data_source_block           2025167
_cod_database_code               7160987
_shelx_shelxl_version_number     2019/3
_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.
;
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.953
_diffrn_oxdiff_ac3_digest_hkl    41853153c08b6aa6549a5fb3d39817a9bc52d3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2. Restrained distances
 N9-H9B = N9-H9A = N1-H1B = N1-H1A
 0.87 with sigma of 0.02
 Cl1-O9 \\sim Cl1-O6 \\sim Cl1-O3 \\sim Cl1-O5 \\sim Cl1-O7 \\sim Cl1-O4
 with sigma of 0.02
3. Rigid bond restraints
 O3, O4, O5, O6, O7, O9
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
O3 \\sim O4 \\sim O5 \\sim O6 \\sim O7 \\sim O9: within 2A with sigma of 0.005
and sigma for terminal atoms of 0.01 within 2A
5. Others
 Sof(O6)=Sof(O7)=Sof(O9)=1-FVAR(1)
 Sof(O3)=Sof(O4)=Sof(O5)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
Cl1 Cl 0.35667(13) 1.08048(11) 0.47589(8) 0.0242(3) Uani 1 1 d D . . . .
O2 O 0.4387(4) 1.1007(4) 0.3819(2) 0.0376(9) Uani 1 1 d . . . . .
O3 O 0.3401(7) 0.9437(4) 0.5010(3) 0.0454(13) Uani 0.850(5) 1 d D U P A 1
O4 O 0.1851(4) 1.1345(4) 0.4704(3) 0.0376(11) Uani 0.850(5) 1 d D U P A 1
O5 O 0.4448(6) 1.1494(5) 0.5525(3) 0.0366(11) Uani 0.850(5) 1 d D U P A 1
O6 O 0.501(3) 0.991(3) 0.5034(16) 0.042(5) Uani 0.150(5) 1 d D U P A 2
O7 O 0.344(4) 1.182(2) 0.5446(16) 0.039(4) Uani 0.150(5) 1 d D U P A 2
O9 O 0.237(3) 0.977(2) 0.463(2) 0.044(4) Uani 0.150(5) 1 d D U P A 2
O1 O 0.6410(4) 0.3400(3) 0.2848(2) 0.0230(7) Uani 1 1 d . . . . .
N1 N 0.3151(5) 0.3943(4) 0.3829(3) 0.0292(10) Uani 1 1 d D . . . .
H1A H 0.222(5) 0.379(5) 0.416(4) 0.044(16) Uiso 1 1 d D . . . .
H1B H 0.375(5) 0.322(3) 0.371(4) 0.027(14) Uiso 1 1 d D . . . .
N2 N 0.3252(5) 0.6170(4) 0.4325(3) 0.0312(9) Uani 1 1 d . . . . .
N3 N 0.4471(5) 0.7151(4) 0.4169(3) 0.0297(10) Uani 1 1 d . . . . .
H3 H 0.436972 0.796627 0.438885 0.036 Uiso 1 1 calc R U . . .
N4 N 0.5473(4) 0.5407(4) 0.3477(3) 0.0200(8) Uani 1 1 d . . . . .
N5 N 0.7201(5) 0.7385(4) 0.3368(3) 0.0243(9) Uani 1 1 d . . . . .
N6 N 0.8080(4) 0.5268(3) 0.2765(3) 0.0195(8) Uani 1 1 d . . . . .
N7 N 0.9478(4) 0.4693(4) 0.2284(3) 0.0206(8) Uani 1 1 d . . . . .
N8 N 0.9832(4) 0.6877(4) 0.2532(3) 0.0220(8) Uani 1 1 d . . . . .
H8 H 1.032670 0.765857 0.252408 0.026 Uiso 1 1 calc R U . . .
N9 N 1.2039(5) 0.5664(5) 0.1715(3) 0.0306(10) Uani 1 1 d D . . . .
H9A H 1.234(8) 0.488(4) 0.150(4) 0.06(2) Uiso 1 1 d D . . . .
H9B H 1.258(6) 0.640(4) 0.160(4) 0.047(18) Uiso 1 1 d D . . . .
C1 C 0.3883(5) 0.5119(5) 0.3907(3) 0.0250(10) Uani 1 1 d . . . . .
C2 C 0.5795(5) 0.6722(5) 0.3657(3) 0.0231(10) Uani 1 1 d . . . . .
C3 C 0.6634(5) 0.4559(4) 0.3004(3) 0.0194(9) Uani 1 1 d . . . . .
C4 C 0.8282(5) 0.6588(4) 0.2920(3) 0.0210(10) Uani 1 1 d . . . . .
C5 C 1.0498(5) 0.5718(4) 0.2151(3) 0.0216(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'
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
O2 Cl1 O4 108.3(2) . . ?
O2 Cl1 O6 88.2(10) . . ?
O3 Cl1 O2 112.8(2) . . ?
O3 Cl1 O4 107.1(3) . . ?
O5 Cl1 O2 110.8(2) . . ?
O5 Cl1 O3 110.2(3) . . ?
O5 Cl1 O4 107.4(3) . . ?
O7 Cl1 O2 121.1(11) . . ?
O7 Cl1 O6 109.5(15) . . ?
O7 Cl1 O9 125.7(16) . . ?
O9 Cl1 O2 107.1(11) . . ?
O9 Cl1 O6 94.6(17) . . ?
H1A N1 H1B 113(5) . . ?
C1 N1 H1A 119(4) . . ?
C1 N1 H1B 122(3) . . ?
C1 N2 N3 105.0(4) . . ?
N2 N3 H3 123.8 . . ?
C2 N3 N2 112.4(4) . . ?
C2 N3 H3 123.8 . . ?
C1 N4 C3 129.4(4) . . ?
C2 N4 C1 106.9(4) . . ?
C2 N4 C3 123.7(4) . . ?
C4 N5 C2 110.6(4) . . ?
C3 N6 N7 122.3(3) . . ?
C4 N6 N7 112.9(4) . . ?
C4 N6 C3 124.8(4) . . ?
C5 N7 N6 102.0(3) . . ?
C4 N8 H8 126.4 . . ?
C4 N8 C5 107.3(4) . . ?
C5 N8 H8 126.4 . . ?
H9A N9 H9B 126(5) . . ?
C5 N9 H9A 115(4) . . ?
C5 N9 H9B 119(4) . . ?
N1 C1 N4 122.4(4) . . ?
N2 C1 N1 127.2(4) . . ?
N2 C1 N4 110.2(4) . . ?
N3 C2 N4 105.5(4) . . ?
N3 C2 N5 129.0(4) . . ?
N5 C2 N4 125.5(4) . . ?
O1 C3 N4 125.6(4) . . ?
O1 C3 N6 125.9(4) . . ?
N6 C3 N4 108.6(4) . . ?
N5 C4 N6 126.8(4) . . ?
N5 C4 N8 128.3(4) . . ?
N8 C4 N6 104.9(4) . . ?
N7 C5 N8 112.9(4) . . ?
N7 C5 N9 124.8(4) . . ?
N9 C5 N8 122.4(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
Cl1 O2 1.436(3) . ?
Cl1 O3 1.431(4) . ?
Cl1 O4 1.449(4) . ?
Cl1 O5 1.424(4) . ?
Cl1 O6 1.490(16) . ?
Cl1 O7 1.386(17) . ?
Cl1 O9 1.417(16) . ?
O1 C3 1.204(5) . ?
N1 H1A 0.87(3) . ?
N1 H1B 0.88(2) . ?
N1 C1 1.324(6) . ?
N2 N3 1.392(5) . ?
N2 C1 1.300(6) . ?
N3 H3 0.8800 . ?
N3 C2 1.318(6) . ?
N4 C1 1.402(5) . ?
N4 C2 1.376(6) . ?
N4 C3 1.403(5) . ?
N5 C2 1.344(6) . ?
N5 C4 1.315(6) . ?
N6 N7 1.397(5) . ?
N6 C3 1.376(5) . ?
N6 C4 1.361(5) . ?
N7 C5 1.319(6) . ?
N8 H8 0.8800 . ?
N8 C4 1.352(6) . ?
N8 C5 1.382(6) . ?
N9 H9A 0.87(3) . ?
N9 H9B 0.87(3) . ?
N9 C5 1.341(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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N3 C2 N4 -1.1(5) . . . . ?
N2 N3 C2 N5 179.9(4) . . . . ?
N3 N2 C1 N1 -177.2(5) . . . . ?
N3 N2 C1 N4 -0.7(5) . . . . ?
N6 N7 C5 N8 1.1(5) . . . . ?
N6 N7 C5 N9 179.6(4) . . . . ?
N7 N6 C3 O1 1.1(7) . . . . ?
N7 N6 C3 N4 180.0(3) . . . . ?
N7 N6 C4 N5 -178.7(4) . . . . ?
N7 N6 C4 N8 0.2(5) . . . . ?
C1 N2 N3 C2 1.1(5) . . . . ?
C1 N4 C2 N3 0.6(5) . . . . ?
C1 N4 C2 N5 179.7(4) . . . . ?
C1 N4 C3 O1 3.4(7) . . . . ?
C1 N4 C3 N6 -175.5(4) . . . . ?
C2 N4 C1 N1 176.8(4) . . . . ?
C2 N4 C1 N2 0.0(5) . . . . ?
C2 N4 C3 O1 178.7(4) . . . . ?
C2 N4 C3 N6 -0.2(5) . . . . ?
C2 N5 C4 N6 -0.9(7) . . . . ?
C2 N5 C4 N8 -179.6(4) . . . . ?
C3 N4 C1 N1 -7.3(7) . . . . ?
C3 N4 C1 N2 175.9(4) . . . . ?
C3 N4 C2 N3 -175.6(4) . . . . ?
C3 N4 C2 N5 3.5(7) . . . . ?
C3 N6 N7 C5 176.3(4) . . . . ?
C3 N6 C4 N5 4.3(7) . . . . ?
C3 N6 C4 N8 -176.8(4) . . . . ?
C4 N5 C2 N3 176.1(5) . . . . ?
C4 N5 C2 N4 -2.8(6) . . . . ?
C4 N6 N7 C5 -0.8(5) . . . . ?
C4 N6 C3 O1 177.8(4) . . . . ?
C4 N6 C3 N4 -3.3(6) . . . . ?
C4 N8 C5 N7 -1.0(5) . . . . ?
C4 N8 C5 N9 -179.6(4) . . . . ?
C5 N8 C4 N5 179.4(4) . . . . ?
C5 N8 C4 N6 0.5(5) . . . . ?
