#------------------------------------------------------------------------------
#$Date: 2025-07-06 15:32:54 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 300521 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/46/7134630.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_7134630
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         'C8 H8 N10 O6, H2 O'
_chemical_formula_sum            'C8 H10 N10 O7'
_chemical_formula_weight         358.26
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2024-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2025-05-28 deposited with the CCDC.	2025-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.071(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.16920(10)
_cell_length_b                   19.0438(4)
_cell_length_c                   13.7975(3)
_cell_measurement_reflns_used    5168
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      75.5020
_cell_measurement_theta_min      4.6400
_cell_volume                     1350.63(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.101a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.101a 64-bit (release 13-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.101a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12835
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.543
_diffrn_reflns_theta_min         3.971
_exptl_absorpt_coefficient_mu    1.358
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0415
_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)+(0.0660P)²+0.2930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1206
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2181
_reflns_number_total             2726
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc02076j2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7134628--7134631.cif.'
_cod_original_cell_volume        1350.62(5)
_cod_database_code               7134630
_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,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O00C(H00I,H00J)
2.b X=CH2 refined with riding coordinates:
 N008(H00A,H00B), N00E(H00C,H00D), N00(H00E,H00F), N00H(H00G,H00H)
;
_shelx_shelxl_version_number     2017/1
_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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.6746(3) 0.68400(8) 0.14680(11) 0.0518(4) Uani 1 1 d . . . . .
N002 N 0.5999(3) 0.59261(8) 0.32519(10) 0.0329(3) Uani 1 1 d . . . . .
O003 O 1.3270(3) 0.44459(9) 0.04690(11) 0.0560(4) Uani 1 1 d . . . . .
N004 N 0.7002(3) 0.48521(8) 0.26605(10) 0.0344(3) Uani 1 1 d . . . . .
O005 O 0.1075(3) 0.68602(8) 0.53629(12) 0.0574(4) Uani 1 1 d . . . . .
O006 O 1.0997(3) 0.35876(8) 0.09353(13) 0.0605(4) Uani 1 1 d . . . . .
N007 N 0.6605(3) 0.66400(8) 0.34242(11) 0.0391(4) Uani 1 1 d . . . . .
N008 N 0.3217(3) 0.50417(8) 0.38225(11) 0.0392(4) Uani 1 1 d . . . . .
H00A H 0.384362 0.472234 0.347346 0.047 Uiso 1 1 calc R . . . .
H00B H 0.201980 0.493752 0.418583 0.047 Uiso 1 1 calc R . . . .
O009 O 0.0294(3) 0.57562(8) 0.50767(12) 0.0576(4) Uani 1 1 d . . . . .
N00A N 1.1548(3) 0.42192(9) 0.09537(11) 0.0424(4) Uani 1 1 d . . . . .
N00B N 0.8868(3) 0.65937(9) 0.17774(12) 0.0424(4) Uani 1 1 d . . . . .
O00C O 0.3373(4) 0.34261(9) 0.33867(15) 0.0668(5) Uani 1 1 d . . . . .
H00I H 0.213573 0.352637 0.372261 0.100 Uiso 1 1 d G . . . .
H00J H 0.332559 0.299069 0.325070 0.100 Uiso 1 1 d G . . . .
N00D N 0.1504(3) 0.63058(9) 0.49390(11) 0.0411(4) Uani 1 1 d . . . . .
N00E N 1.2413(3) 0.57222(10) 0.09842(12) 0.0443(4) Uani 1 1 d . . . . .
H00C H 1.257648 0.617152 0.097457 0.053 Uiso 1 1 calc R . . . .
H00D H 1.340195 0.546246 0.067092 0.053 Uiso 1 1 calc R . . . .
O00F O 1.0886(3) 0.69348(9) 0.18706(17) 0.0744(6) Uani 1 1 d . . . . .
N00 N 0.7591(4) 0.37515(9) 0.21581(13) 0.0504(4) Uani 1 1 d . . . . .
H00E H 0.645678 0.362850 0.253877 0.061 Uiso 1 1 calc R . . . .
H00F H 0.829740 0.344004 0.181946 0.061 Uiso 1 1 calc R . . . .
N00H N 0.4907(4) 0.75177(9) 0.43555(13) 0.0512(4) Uani 1 1 d . . . . .
H00G H 0.594214 0.782815 0.415966 0.061 Uiso 1 1 calc R . . . .
H00H H 0.381410 0.763280 0.475673 0.061 Uiso 1 1 calc R . . . .
C00I C 0.7326(3) 0.55352(9) 0.26137(11) 0.0307(3) Uani 1 1 d . . . . .
C00J C 1.0621(3) 0.54276(10) 0.14861(11) 0.0340(4) Uani 1 1 d . . . . .
C00K C 0.8994(3) 0.58514(9) 0.20013(12) 0.0337(4) Uani 1 1 d . . . . .
C00L C 0.4093(3) 0.56905(9) 0.38005(12) 0.0321(4) Uani 1 1 d . . . . .
C00M C 0.3367(3) 0.62885(9) 0.42908(12) 0.0352(4) Uani 1 1 d . . . . .
C00N C 0.8247(3) 0.44180(10) 0.20937(12) 0.0352(4) Uani 1 1 d . . . . .
C00O C 1.0176(3) 0.46866(10) 0.15110(12) 0.0349(4) Uani 1 1 d . . . . .
C00P C 0.4996(4) 0.68506(9) 0.40333(13) 0.0369(4) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C00I N002 N007 120.53(13) . . ?
C00L N002 N007 112.34(13) . . ?
C00L N002 C00I 127.09(15) . . ?
C00I N004 C00N 120.52(15) . . ?
C00P N007 N002 105.02(13) . . ?
H00A N008 H00B 120.0 . . ?
C00L N008 H00A 120.0 . . ?
C00L N008 H00B 120.0 . . ?
O003 N00A C00O 120.09(18) . . ?
O006 N00A O003 120.15(16) . . ?
O006 N00A C00O 119.74(16) . . ?
O001 N00B C00K 117.76(15) . . ?
O00F N00B O001 123.65(18) . . ?
O00F N00B C00K 118.54(16) . . ?
H00I O00C H00J 109.5 . . ?
O005 N00D O009 121.82(16) . . ?
O005 N00D C00M 119.85(16) . . ?
O009 N00D C00M 118.32(16) . . ?
H00C N00E H00D 120.0 . . ?
C00J N00E H00C 120.0 . . ?
C00J N00E H00D 120.0 . . ?
H00E N00 H00F 120.0 . . ?
C00N N00 H00E 120.0 . . ?
C00N N00 H00F 120.0 . . ?
H00G N00H H00H 120.0 . . ?
C00P N00H H00G 120.0 . . ?
C00P N00H H00H 120.0 . . ?
N002 C00I C00K 121.83(16) . . ?
N004 C00I N002 115.20(14) . . ?
N004 C00I C00K 122.90(16) . . ?
N00E C00J C00K 120.23(18) . . ?
N00E C00J C00O 123.24(16) . . ?
C00K C00J C00O 116.50(15) . . ?
C00I C00K N00B 122.05(15) . . ?
C00I C00K C00J 119.62(16) . . ?
C00J C00K N00B 117.84(15) . . ?
N002 C00L C00M 104.16(15) . . ?
N008 C00L N002 125.78(16) . . ?
N008 C00L C00M 130.05(16) . . ?
N00D C00M C00L 125.05(16) . . ?
N00D C00M C00P 127.72(16) . . ?
C00L C00M C00P 107.15(15) . . ?
N004 C00N C00O 120.51(17) . . ?
N00 C00N N004 114.16(16) . . ?
N00 C00N C00O 125.29(17) . . ?
N00A C00O C00J 121.10(16) . . ?
N00A C00O C00N 119.77(17) . . ?
C00J C00O C00N 119.11(15) . . ?
N007 C00P N00H 123.20(17) . . ?
N007 C00P C00M 111.21(16) . . ?
N00H C00P C00M 125.58(17) . . ?
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
O001 N00B 1.228(2) . ?
N002 N007 1.410(2) . ?
N002 C00I 1.389(2) . ?
N002 C00L 1.379(2) . ?
O003 N00A 1.246(2) . ?
N004 C00I 1.314(2) . ?
N004 C00N 1.347(2) . ?
O005 N00D 1.238(2) . ?
O006 N00A 1.236(2) . ?
N007 C00P 1.306(2) . ?
N008 H00A 0.8600 . ?
N008 H00B 0.8600 . ?
N008 C00L 1.317(2) . ?
O009 N00D 1.244(2) . ?
N00A C00O 1.415(2) . ?
N00B O00F 1.224(2) . ?
N00B C00K 1.447(2) . ?
O00C H00I 0.8503 . ?
O00C H00J 0.8499 . ?
N00D C00M 1.382(2) . ?
N00E H00C 0.8600 . ?
N00E H00D 0.8600 . ?
N00E C00J 1.337(2) . ?
N00 H00E 0.8600 . ?
N00 H00F 0.8600 . ?
N00 C00N 1.319(2) . ?
N00H H00G 0.8600 . ?
N00H H00H 0.8600 . ?
N00H C00P 1.348(2) . ?
C00I C00K 1.405(2) . ?
C00J C00K 1.411(2) . ?
C00J C00O 1.431(3) . ?
C00L C00M 1.396(3) . ?
C00M C00P 1.430(2) . ?
C00N C00O 1.439(2) . ?
