#------------------------------------------------------------------------------
#$Date: 2024-01-06 09:59:50 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288796 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247735.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_7247735
loop_
_publ_author_name
'Baraboshkin, Nikita M.'
'Zelenov, Victor P.'
'Fedyanin, Ivan V.'
_publ_section_title
;
 What are the prospects of [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxides,
 1,5-dioxides and their nitro derivatives as high-energy-density
 materials? Synthesis, experimental and predicted crystal structures, and
 calculated explosive properties
;
_journal_issue                   48
_journal_name_full               CrystEngComm
_journal_page_first              6719
_journal_page_last               6739
_journal_paper_doi               10.1039/D3CE00964E
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C8 H3 N5 O4'
_chemical_formula_sum            'C8 H3 N5 O4'
_chemical_formula_weight         233.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-04-11
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2023-08-15 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2846(2)
_cell_length_b                   9.99780(10)
_cell_length_c                   6.38630(10)
_cell_measurement_reflns_used    5599
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      76.9440
_cell_measurement_theta_min      5.3760
_cell_volume                     912.06(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -64.00   0.50    1.00    --  -48.70-139.00  13.00  112
  2  ω   -122.00 -39.00   0.50    1.00    --  -48.70 -22.00  45.00  166
  3  ω    -28.00  26.00   0.50    1.00    --  -48.70  22.00-148.00  108
  4  ω   -156.00 -84.00   0.50    3.87    --  -86.25-103.00 -96.00  144
  5  ω    -90.00 -16.00   0.50    3.87    --  -86.25 131.00-100.00  148
  6  ω     38.00 116.00   0.50    3.87    --  107.75-131.00-171.00  156
  7  ω     97.00 178.00   0.50    3.87    --  107.75  22.00-148.00  162
  8  ω     46.00 121.00   0.50    3.87    --  107.75-139.00  13.00  150
  9  ω     71.00  97.00   0.50    3.87    --  107.75-103.00 -96.00   52
 10  ω    -22.00  25.00   0.50    1.00    --   48.70 -19.00 -90.00   94
 11  ω     37.00  71.00   0.50    3.87    --  107.75 -61.00  30.00   68
 12  ω     40.00  72.00   0.50    3.87    --  107.75-125.00 -30.00   64
 13  ω     49.00  75.00   0.50    3.87    --  107.75 -95.00  30.00   52
 14  ω     39.00  65.00   0.50    3.87    --  107.75-103.00 -34.16   52
 15  ω     36.00  69.00   0.50    3.87    --  107.75 -95.00  90.00   66
 16  ω    138.00 178.00   0.50    3.87    --  107.75  45.00 -60.00   80
 17  ω     83.00 109.00   0.50    3.87    --  107.75-125.00 -30.00   52
 18  ω     39.00  70.00   0.50    3.87    --  107.75 -61.00-150.00   62
 19  ω    147.00 177.00   0.50    3.87    --  107.75  30.00  90.00   60
 20  ω     41.00  69.00   0.50    3.87    --  107.75 -61.00 -30.00   56
 21  ω     69.00 106.00   0.50    3.87    --  107.75-103.00 -34.16   74
 22  ω     43.00  69.00   0.50    3.87    --  107.75-125.00   0.00   52
 23  ω     84.00 110.00   0.50    3.87    --  107.75-125.00  90.00   52
 24  ω    109.00 135.00   0.50    3.87    --  107.75  45.00  27.49   52
 25  ω     36.00  61.00   0.50    3.87    --  107.75 -61.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0776967000
_diffrn_orient_matrix_UB_12      0.1032424000
_diffrn_orient_matrix_UB_13      0.0430505000
_diffrn_orient_matrix_UB_21      -0.0747014000
_diffrn_orient_matrix_UB_22      -0.1056354000
_diffrn_orient_matrix_UB_23      -0.0537301000
_diffrn_orient_matrix_UB_31      -0.0030715000
_diffrn_orient_matrix_UB_32      -0.0438743000
_diffrn_orient_matrix_UB_33      0.2312489000
_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  0.0227
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            6846
_diffrn_reflns_point_group_measured_fraction_full 0.777
_diffrn_reflns_point_group_measured_fraction_max 0.758
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.814
_diffrn_reflns_theta_min         5.401
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.229
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.491
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 396 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1472
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0238
_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)+(0.0316P)²+0.2094P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0625
_reflns_Friedel_coverage         0.389
_reflns_Friedel_fraction_full    0.507
_reflns_Friedel_fraction_max     0.468
_reflns_number_gt                1441
_reflns_number_total             1472
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00964e2.cif
_cod_data_source_block           Z461401
_cod_depositor_comments
'Adding full bibliography for 7247734--7247739.cif.'
_cod_database_code               7247735
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C8H3N5O4
_chemical_oxdiff_usercomment     Z461401
_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   0.976
_shelx_estimated_absorpt_t_min   0.551
_reflns_odcompleteness_completeness 98.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.52
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11)
;
_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 1.150
_oxdiff_exptl_absorpt_empirical_full_min 0.793
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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
O2 O 0.61276(10) 0.88331(15) 0.6833(3) 0.0347(4) Uani 1 1 d . . . . .
O6 O 0.38947(9) 0.45745(13) 0.9105(2) 0.0253(3) Uani 1 1 d . . . . .
O15 O 0.16963(9) 0.36458(13) 0.3766(3) 0.0255(3) Uani 1 1 d . . . . .
O16 O 0.17178(10) 0.47825(14) 0.0886(3) 0.0321(4) Uani 1 1 d . . . . .
N1 N 0.54587(11) 0.86765(17) 0.5252(3) 0.0292(4) Uani 1 1 d . . . . .
N3 N 0.60246(11) 0.79113(18) 0.8420(3) 0.0323(4) Uani 1 1 d . . . . .
N5 N 0.49493(11) 0.61649(16) 0.9012(3) 0.0249(3) Uani 1 1 d . . . . .
N6 N 0.42463(10) 0.55456(15) 0.8153(3) 0.0210(3) Uani 1 1 d . . . . .
N14 N 0.19877(10) 0.45596(14) 0.2653(3) 0.0213(3) Uani 1 1 d . . . . .
C4 C 0.52949(12) 0.72054(18) 0.7831(3) 0.0244(4) Uani 1 1 d . . . . .
C7 C 0.38305(11) 0.59027(17) 0.6146(3) 0.0181(4) Uani 1 1 d . . . . .
C8 C 0.31014(11) 0.51031(17) 0.5430(3) 0.0191(4) Uani 1 1 d . . . . .
H8 H 0.287360 0.436729 0.622182 0.023 Uiso 1 1 calc R U . . .
C9 C 0.27276(11) 0.54349(17) 0.3514(3) 0.0192(4) Uani 1 1 d . . . . .
C10 C 0.30145(13) 0.65245(18) 0.2327(3) 0.0223(4) Uani 1 1 d . . . . .
H10 H 0.271862 0.672884 0.103332 0.027 Uiso 1 1 calc R U . . .
C11 C 0.37410(12) 0.73047(18) 0.3072(3) 0.0225(4) Uani 1 1 d . . . . .
H11 H 0.395160 0.805487 0.229000 0.027 Uiso 1 1 calc R U . . .
C12 C 0.41640(12) 0.69856(17) 0.4980(3) 0.0201(4) Uani 1 1 d . . . . .
C13 C 0.49534(12) 0.76687(17) 0.5902(3) 0.0218(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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 0 0.0120
-1 -1 0 0.0120
0 0 1 0.2971
0 0 -1 0.2484
0 1 0 0.0145
0 -1 0 0.0187
-1 1 0 0.0078
1 -1 0 0.0180
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
N3 O2 N1 112.52(13) . . ?
C13 N1 O2 103.56(17) . . ?
C4 N3 O2 103.50(17) . . ?
N6 N5 C4 113.92(17) . . ?
O6 N6 N5 118.31(16) . . ?
O6 N6 C7 117.01(15) . . ?
N5 N6 C7 124.68(16) . . ?
O15 N14 C9 117.80(15) . . ?
O16 N14 O15 124.52(16) . . ?
O16 N14 C9 117.68(15) . . ?
N3 C4 N5 122.25(19) . . ?
N3 C4 C13 110.47(18) . . ?
N5 C4 C13 127.28(17) . . ?
C8 C7 N6 116.98(16) . . ?
C8 C7 C12 121.72(17) . . ?
C12 C7 N6 121.29(16) . . ?
C7 C8 H8 121.8 . . ?
C9 C8 C7 116.39(16) . . ?
C9 C8 H8 121.8 . . ?
C8 C9 N14 117.75(15) . . ?
C8 C9 C10 124.07(17) . . ?
C10 C9 N14 118.17(16) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.41(18) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.74(17) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C13 114.55(17) . . ?
C11 C12 C7 119.61(16) . . ?
C11 C12 C13 125.83(17) . . ?
N1 C13 C4 109.94(17) . . ?
N1 C13 C12 131.81(19) . . ?
C4 C13 C12 118.24(16) . . ?
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
O2 N1 1.399(2) . ?
O2 N3 1.378(3) . ?
O6 N6 1.251(2) . ?
O15 N14 1.230(2) . ?
O16 N14 1.213(2) . ?
N1 C13 1.307(2) . ?
N3 C4 1.314(2) . ?
N5 N6 1.301(2) . ?
N5 C4 1.377(3) . ?
N6 C7 1.457(2) . ?
N14 C9 1.478(2) . ?
C4 C13 1.404(3) . ?
C7 C8 1.390(2) . ?
C7 C12 1.398(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.376(3) . ?
C9 C10 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.397(3) . ?
C12 C13 1.444(2) . ?
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
O2 N1 C13 C4 -0.05(19) . . . . ?
O2 N1 C13 C12 -178.56(18) . . . . ?
O2 N3 C4 N5 -179.61(17) . . . . ?
O2 N3 C4 C13 0.6(2) . . . . ?
O6 N6 C7 C8 -2.2(2) . . . . ?
O6 N6 C7 C12 178.94(15) . . . . ?
O15 N14 C9 C8 5.6(2) . . . . ?
O15 N14 C9 C10 -175.60(17) . . . . ?
O16 N14 C9 C8 -173.56(17) . . . . ?
O16 N14 C9 C10 5.3(2) . . . . ?
N1 O2 N3 C4 -0.6(2) . . . . ?
N3 O2 N1 C13 0.4(2) . . . . ?
N3 C4 C13 N1 -0.3(2) . . . . ?
N3 C4 C13 C12 178.40(16) . . . . ?
N5 N6 C7 C8 177.92(16) . . . . ?
N5 N6 C7 C12 -0.9(3) . . . . ?
N5 C4 C13 N1 179.84(17) . . . . ?
N5 C4 C13 C12 -1.4(3) . . . . ?
N6 N5 C4 N3 -177.55(17) . . . . ?
N6 N5 C4 C13 2.3(3) . . . . ?
N6 C7 C8 C9 -178.74(15) . . . . ?
N6 C7 C12 C11 -179.37(15) . . . . ?
N6 C7 C12 C13 1.7(2) . . . . ?
N14 C9 C10 C11 -176.56(16) . . . . ?
C4 N5 N6 O6 179.12(15) . . . . ?
C4 N5 N6 C7 -1.1(2) . . . . ?
C7 C8 C9 N14 176.62(15) . . . . ?
C7 C8 C9 C10 -2.2(3) . . . . ?
C7 C12 C13 N1 177.76(18) . . . . ?
C7 C12 C13 C4 -0.6(2) . . . . ?
C8 C7 C12 C11 1.9(3) . . . . ?
C8 C7 C12 C13 -177.06(16) . . . . ?
C8 C9 C10 C11 2.2(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C7 -1.8(3) . . . . ?
C10 C11 C12 C13 176.97(17) . . . . ?
C11 C12 C13 N1 -1.1(3) . . . . ?
C11 C12 C13 C4 -179.50(16) . . . . ?
C12 C7 C8 C9 0.1(2) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9984 0.9997 0.0001 0.0256 -0.1802 -0.0469
-0.9984 -0.9997 -0.0001 -0.0256 0.1802 0.0469
0.0003 -0.0007 0.9998 0.0429 -0.0537 0.2312
-0.0003 0.0007 -0.9998 -0.0429 0.0537 -0.2312
-0.0009 0.9990 -0.0002 0.1032 -0.1055 -0.0439
0.0009 -0.9990 0.0002 -0.1032 0.1055 0.0439
-1.0001 0.9983 -0.0004 0.1808 -0.0307 -0.0408
1.0001 -0.9983 0.0004 -0.1808 0.0307 0.0408
