#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:25:39 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290215 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/50/7715064.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_7715064
loop_
_publ_author_name
'Guo, Xiaoyu'
'Feng, Yizhen'
'Zhi, Shengjie'
'Fu, Yajie'
'Liu, Yingle'
'Liu, Qiangqiang'
'Gao, Haixiang'
_publ_section_title
;
 Obtaining superior high-density fused-ring energetic materials via
 the introduction of carbonyl, o-NH₂-NO₂ and
 nitroamino groups.
;
_journal_issue                   9
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4035
_journal_page_last               4040
_journal_paper_doi               10.1039/d3dt04237e
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C6 H4 N6 O5, H2 O'
_chemical_formula_sum            'C6 H6 N6 O6'
_chemical_formula_weight         258.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-01
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-11-07 deposited with the CCDC.	2024-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.747(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1700(2)
_cell_length_b                   6.5296(2)
_cell_length_c                   15.4974(4)
_cell_measurement_reflns_used    2197
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      72.9240
_cell_measurement_theta_min      5.7550
_cell_volume                     919.46(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      8.00  33.00   1.00    1.00    --  -40.73  38.00  30.00   25
  2  ω    -62.00  -7.00   1.00    1.00    --  -40.73  38.00  30.00   55
  3  ω    -61.00  -9.00   1.00    1.00    --  -40.73  77.00  90.00   52
  4  ω     21.00 110.00   1.00    1.00    --   40.73  57.00-180.00   89
  5  ω     34.00  96.00   1.00    1.00    --  106.95 -45.00-120.00   62
  6  ω     91.00 155.00   1.00    1.00    --  106.95  45.00   0.00   64
  7  ω    144.00 171.00   1.00    1.00    --  106.95 125.00   0.00   27
  8  ω     35.00 118.00   1.00    1.00    --  106.95 -45.00 150.00   83
  9  ω     35.00 106.00   1.00    1.00    --  106.95 -95.00 120.00   71
 10  ω     37.00 113.00   1.00    1.00    --  106.95-125.00  60.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0943627000
_diffrn_orient_matrix_UB_12      0.1060854000
_diffrn_orient_matrix_UB_13      -0.0619351000
_diffrn_orient_matrix_UB_21      0.0191479000
_diffrn_orient_matrix_UB_22      -0.2063224000
_diffrn_orient_matrix_UB_23      -0.0454490000
_diffrn_orient_matrix_UB_31      -0.1394905000
_diffrn_orient_matrix_UB_32      0.0432852000
_diffrn_orient_matrix_UB_33      -0.0645198000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3074
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.046
_diffrn_reflns_theta_min         5.312
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.481
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0040(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         1769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0351
_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)+(0.0501P)²+0.3480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1612
_reflns_number_total             1769
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt04237e2.cif
_cod_data_source_block           0927-1
_cod_depositor_comments
'Adding full bibliography for 7715064--7715066.cif.'
_cod_database_code               7715064
_shelx_shelxl_version_number     2017/1
_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 C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), C1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.800
_oxdiff_exptl_absorpt_empirical_full_min 0.557
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.35624(13) 0.86167(18) 0.23950(7) 0.0301(3) Uani 1 1 d . . . . .
O2 O 0.45689(12) 0.58470(17) 0.29784(7) 0.0280(3) Uani 1 1 d . . . . .
O3 O 0.39073(12) 0.16023(18) 0.54416(7) 0.0289(3) Uani 1 1 d . . . . .
O4 O 0.24188(17) 0.1442(2) 0.67781(10) 0.0527(4) Uani 1 1 d . . . . .
O5 O 0.07919(13) 0.37404(18) 0.69201(7) 0.0298(3) Uani 1 1 d . . . . .
N1 N 0.37225(13) 0.73139(19) 0.29784(8) 0.0217(3) Uani 1 1 d . . . . .
N2 N 0.13370(14) 0.8798(2) 0.45395(8) 0.0238(3) Uani 1 1 d . . . . .
N3 N 0.18682(13) 0.68933(19) 0.48310(8) 0.0193(3) Uani 1 1 d . . . . .
N4 N 0.34313(13) 0.42416(19) 0.45316(8) 0.0210(3) Uani 1 1 d . . . . .
H4 H 0.399979 0.369432 0.417926 0.025 Uiso 1 1 calc R U . . .
N5 N 0.05976(15) 0.7082(2) 0.59923(9) 0.0254(3) Uani 1 1 d . . . . .
H5A H 0.037(2) 0.829(3) 0.5796(13) 0.033(5) Uiso 1 1 d . . . . .
H5B H 0.037(2) 0.660(3) 0.6458(14) 0.041(6) Uiso 1 1 d . . . . .
N6 N 0.17892(14) 0.3022(2) 0.65374(8) 0.0245(3) Uani 1 1 d . . . . .
C1 C 0.19657(17) 0.9117(2) 0.38410(10) 0.0239(3) Uani 1 1 d . . . . .
H1 H 0.181555 1.031124 0.349000 0.029 Uiso 1 1 calc R U . . .
C2 C 0.28866(15) 0.7492(2) 0.36709(9) 0.0203(3) Uani 1 1 d . . . . .
C3 C 0.28131(15) 0.6072(2) 0.43252(9) 0.0190(3) Uani 1 1 d . . . . .
C4 C 0.32084(16) 0.3173(2) 0.52818(9) 0.0215(3) Uani 1 1 d . . . . .
C5 C 0.21428(16) 0.4083(2) 0.57889(9) 0.0207(3) Uani 1 1 d . . . . .
C6 C 0.15014(15) 0.6003(2) 0.55845(9) 0.0193(3) Uani 1 1 d . . . . .
O6 O 0.54659(13) 0.21151(18) 0.37593(7) 0.0298(3) Uani 1 1 d G . . . .
H6A H 0.572151 0.092249 0.394090 0.045 Uiso 1 1 d G U . . .
H6B H 0.557081 0.210004 0.322277 0.045 Uiso 1 1 d G U . . .
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
O1 N1 C2 118.60(12) . . ?
O2 N1 O1 123.21(12) . . ?
O2 N1 C2 118.18(12) . . ?
C1 N2 N3 103.72(12) . . ?
C3 N3 N2 112.94(12) . . ?
C3 N3 C6 124.63(13) . . ?
C6 N3 N2 122.38(12) . . ?
C3 N4 H4 118.7 . . ?
C3 N4 C4 122.63(12) . . ?
C4 N4 H4 118.7 . . ?
H5A N5 H5B 125(2) . . ?
C6 N5 H5A 117.3(14) . . ?
C6 N5 H5B 117.2(15) . . ?
O4 N6 O5 121.44(13) . . ?
O4 N6 C5 120.74(13) . . ?
O5 N6 C5 117.79(13) . . ?
N2 C1 H1 123.9 . . ?
N2 C1 C2 112.20(14) . . ?
C2 C1 H1 123.9 . . ?
C1 C2 N1 127.58(14) . . ?
C3 C2 N1 126.20(13) . . ?
C3 C2 C1 106.22(13) . . ?
N3 C3 C2 104.92(12) . . ?
N4 C3 N3 119.78(13) . . ?
N4 C3 C2 135.30(13) . . ?
O3 C4 N4 117.31(13) . . ?
O3 C4 C5 127.26(14) . . ?
N4 C4 C5 115.43(13) . . ?
N6 C5 C4 118.85(13) . . ?
C6 C5 N6 118.92(13) . . ?
C6 C5 C4 122.17(13) . . ?
N3 C6 C5 115.04(13) . . ?
N5 C6 N3 114.89(14) . . ?
N5 C6 C5 130.06(14) . . ?
H6A O6 H6B 104.5 . . ?
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
O1 N1 1.2357(17) . ?
O2 N1 1.2328(16) . ?
O3 C4 1.2172(18) . ?
O4 N6 1.2161(18) . ?
O5 N6 1.2468(17) . ?
N1 C2 1.4052(18) . ?
N2 N3 1.3888(17) . ?
N2 C1 1.310(2) . ?
N3 C3 1.3549(18) . ?
N3 C6 1.3857(18) . ?
N4 H4 0.8800 . ?
N4 C3 1.3430(19) . ?
N4 C4 1.3943(19) . ?
N5 H5A 0.86(2) . ?
N5 H5B 0.84(2) . ?
N5 C6 1.3132(19) . ?
N6 C5 1.4254(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.403(2) . ?
C2 C3 1.382(2) . ?
C4 C5 1.460(2) . ?
C5 C6 1.403(2) . ?
O6 H6A 0.8502 . ?
O6 H6B 0.8499 . ?
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
O1 N1 C2 C1 -7.1(2) . . . . ?
O1 N1 C2 C3 172.87(14) . . . . ?
O2 N1 C2 C1 173.78(14) . . . . ?
O2 N1 C2 C3 -6.3(2) . . . . ?
O3 C4 C5 N6 -3.3(2) . . . . ?
O3 C4 C5 C6 174.00(15) . . . . ?
O4 N6 C5 C4 3.9(2) . . . . ?
O4 N6 C5 C6 -173.57(15) . . . . ?
O5 N6 C5 C4 -174.35(13) . . . . ?
O5 N6 C5 C6 8.2(2) . . . . ?
N1 C2 C3 N3 -179.37(13) . . . . ?
N1 C2 C3 N4 0.7(3) . . . . ?
N2 N3 C3 N4 179.25(12) . . . . ?
N2 N3 C3 C2 -0.71(16) . . . . ?
N2 N3 C6 N5 1.0(2) . . . . ?
N2 N3 C6 C5 -179.50(12) . . . . ?
N2 C1 C2 N1 179.66(14) . . . . ?
N2 C1 C2 C3 -0.28(18) . . . . ?
N3 N2 C1 C2 -0.14(17) . . . . ?
N4 C4 C5 N6 176.39(12) . . . . ?
N4 C4 C5 C6 -6.3(2) . . . . ?
N6 C5 C6 N3 -177.97(12) . . . . ?
N6 C5 C6 N5 1.4(2) . . . . ?
C1 N2 N3 C3 0.54(16) . . . . ?
C1 N2 N3 C6 177.90(13) . . . . ?
C1 C2 C3 N3 0.58(16) . . . . ?
C1 C2 C3 N4 -179.37(16) . . . . ?
C3 N3 C6 N5 178.05(13) . . . . ?
C3 N3 C6 C5 -2.5(2) . . . . ?
C3 N4 C4 O3 -174.57(13) . . . . ?
C3 N4 C4 C5 5.7(2) . . . . ?
C4 N4 C3 N3 -3.7(2) . . . . ?
C4 N4 C3 C2 176.24(15) . . . . ?
C4 C5 C6 N3 4.7(2) . . . . ?
C4 C5 C6 N5 -175.92(15) . . . . ?
C6 N3 C3 N4 2.0(2) . . . . ?
C6 N3 C3 C2 -178.00(13) . . . . ?
