#------------------------------------------------------------------------------
#$Date: 2025-08-23 01:57:28 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301878 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/64/7706459.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_7706459
loop_
_publ_author_name
'Tang, Yongxing'
'Li, Kejia'
'Chinnam, Ajay Kumar'
'Staples, Richard J.'
'Shreeve, Jean'ne M.'
_publ_section_title
;
 Mono-N-oxidation of heterocycle-fused pyrimidines.
;
_journal_issue                   6
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2143
_journal_page_last               2148
_journal_paper_doi               10.1039/d0dt03260c
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         '2(Cl), C5 H8 N6 O'
_chemical_formula_sum            'C5 H8 Cl2 N6 O'
_chemical_formula_weight         239.07
_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             2020-10-26
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.10.11 svn.r5b043f8a for OlexSys, GUI svn.r6175)
;
_audit_update_record
;
2020-10-27 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                79.811(2)
_cell_angle_beta                 75.385(2)
_cell_angle_gamma                76.143(2)
_cell_formula_units_Z            2
_cell_length_a                   6.3903(2)
_cell_length_b                   7.8053(2)
_cell_length_c                   9.9575(2)
_cell_measurement_reflns_used    5784
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.7140
_cell_measurement_theta_min      8.3850
_cell_volume                     463.01(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  31.00   0.50    0.05    --   14.00  43.00  42.27   52
  2  ω    137.00 172.00   0.50    0.20    --  107.11  57.00  90.00   70
  3  ω    115.00 165.00   0.50    0.20    --  107.11  37.00 120.00  100
  4  ω    117.00 154.00   0.50    0.20    --  107.11  37.00  60.00   74
  5  ω    126.00 167.00   0.50    0.20    --  107.11  77.00   0.00   82
  6  ω    122.00 151.00   0.50    0.20    --  107.11  37.00 -90.00   58
  7  ω    105.00 155.00   0.50    0.20    --  107.11  19.00  30.00  100
  8  ω    114.00 176.00   0.50    0.20    --  107.11  37.00-120.00  124
  9  ω    128.00 174.00   0.50    0.20    --  107.11  77.00-180.00   92
 10  ω    105.00 149.00   0.50    0.20    --  107.11  19.00-180.00   88
 11  ω     77.00 103.00   0.50    0.20    --   86.00  29.00-177.42   52
 12  ω    -23.00  18.00   0.50    0.05    --  -47.57  19.00-150.00   82
 13  ω    -86.00 -61.00   0.50    0.05    --  -47.57 147.00 -72.00   50
 14  ω    -66.00 -26.00   0.50    0.20    --  -86.25  57.00 120.00   80
 15  ω    -72.00 -47.00   0.50    0.20    --  -86.25 124.00 123.00   50
 16  ω    -81.00 -36.00   0.50    0.05    --  -47.57 124.00 123.00   90
 17  ω     36.00  97.00   0.50    0.20    --  107.11 -99.00-120.00  122
 18  ω     36.00 102.00   0.50    0.20    --  107.11-125.00-180.00  132
 19  ω     51.00 124.00   0.50    0.20    --  107.11-147.00-121.00  146
 20  ω     75.00 100.00   0.50    0.05    --   47.57-147.00-121.00   50
 21  ω     46.00 105.00   0.50    0.20    --  107.11-125.00   0.00  118
 22  ω     77.00 103.00   0.50    0.20    --  107.11 -99.00 -30.00   52
 23  ω     64.00 108.00   0.50    0.20    --  107.11-124.00  43.00   88
 24  ω     81.00 107.00   0.50    0.20    --  107.11-125.00  90.00   52
 25  ω     47.00  78.00   0.50    0.20    --  107.11-125.00  90.00   62
 26  ω     54.00  80.00   0.50    0.05    --   47.57-124.00  43.00   52
 27  ω     35.00  65.00   0.50    0.20    --  107.11 -57.00   0.00   60
 28  ω     39.00  64.00   0.50    0.20    --  107.11 -57.00  60.00   50
 29  ω     35.00  61.00   0.50    0.20    --  107.11 -57.00  90.00   52
 30  ω    -18.00  25.00   0.50    0.05    --   47.57 -19.00  30.00   86
 31  ω     39.00  65.00   0.50    0.20    --  107.11 -57.00-150.00   52
 32  ω     99.00 124.00   0.50    0.20    --  107.11 147.00 -72.00   50
 33  ω    107.00 177.00   0.50    0.20    --  107.11 125.00  30.00  140
 34  ω    101.00 151.00   0.50    0.20    --  107.11 124.00 123.00  100
 35  ω    -91.00 -39.00   0.50    0.05    --  -47.57 -25.00  65.75  104
 36  ω    -36.00 -11.00   0.50    0.05    --  -22.00 -40.00 -24.66   50
 37  ω    -30.00  -1.00   0.50    0.05    --  -14.00 -43.00 -67.59   58
 38  ω    -47.00 -21.00   0.50    0.05    --  -34.00 -34.00-118.57   52
 39  ω    -54.00 -29.00   0.50    0.05    --  -42.00 -33.00 -57.50   50
 40  ω    -58.00 -33.00   0.50    0.05    --  -42.00 -32.00-129.89   50
 41  ω    -17.00   9.00   0.50    0.05    --   -6.00 -55.00  15.65   52
 42  ω    -40.00 -15.00   0.50    0.05    --  -26.00 -38.00  98.23   50
 43  ω    -39.00 -13.00   0.50    0.05    --  -26.00 -38.00 149.19   52
 44  ω    -64.00 -39.00   0.50    0.05    --  -46.00 -31.00  91.42   50
 45  ω    -94.00 -36.00   0.50    0.05    --  -47.57 -30.00-160.65  116
 46  ω   -138.00 -73.00   0.50    0.20    --  -86.25 -25.00 -67.35  130
 47  ω   -145.00-107.00   0.50    0.20    --  -70.00 -29.00   0.53   76
 48  ω    -95.00 -69.00   0.50    0.20    --  -82.00 -30.00 -21.88   52
 49  ω    -86.00 -61.00   0.50    0.20    --  -74.00 -29.00  53.16   50
 50  ω   -127.00-101.00   0.50    0.20    --  -74.00 -29.00  53.16   52
 51  ω   -122.00 -97.00   0.50    0.05    --  -58.00 -30.00 167.08   50
 52  ω    -85.00 -49.00   0.50    0.05    --  -58.00 -30.00 167.08   72
 53  ω   -110.00 -80.00   0.50    0.20    --  -86.25 -29.00 163.45   60
 54  ω   -120.00 -69.00   0.50    0.20    --  -82.00 -30.00 136.51  102
 55  ω   -125.00 -80.00   0.50    0.20    --  -86.25 -29.00  31.90   90
 56  ω    -93.00 -58.00   0.50    0.20    --  -70.00 -29.00  41.34   70
 57  ω    -88.00 -57.00   0.50    0.20    --  -70.00 -29.00   0.53   62
 58  ω   -106.00 -74.00   0.50    0.20    --  -86.25 -29.00 -71.03   64
 59  ω    -92.00 -63.00   0.50    0.20    --  -74.00 -29.00-120.66   58
 60  ω   -111.00 -75.00   0.50    0.20    --  -86.25 -29.00-140.56   72
 61  ω   -129.00 -81.00   0.50    0.20    --  -86.25 -29.00-164.21   96
 62  ω   -161.00-125.00   0.50    0.20    --  -86.25 -27.00 -36.46   72
 63  ω   -106.00 -74.00   0.50    0.20    --  -86.25 -26.00 -99.60   64
 64  ω   -115.00 -80.00   0.50    0.20    --  -86.25 -27.00 -36.46   70
 65  ω   -136.00-110.00   0.50    0.20    --  -86.25 -26.00 -99.60   52
 66  ω   -125.00 -99.00   0.50    0.20    --  -86.25 -28.00  45.00   52
 67  ω    -98.00 -73.00   0.50    0.20    --  -86.25 -28.00  45.00   50
 68  ω   -150.00 -73.00   0.50    0.20    --  -86.25 -28.00  98.35  154
 69  ω   -129.00-104.00   0.50    0.20    --  -86.25-124.00  43.00   50
 70  ω    -90.00 -65.00   0.50    0.05    --  -47.57-147.00-121.00   50
 71  ω   -145.00 -78.00   0.50    0.20    --  -86.25-147.00-121.00  134
 72  ω    -51.00 -25.00   0.50    0.20    --  -86.25 118.00 135.00   52
 73  ω    -27.00  -2.00   0.50    0.05    --  -14.00 -46.00 139.98   50
 74  ω      5.00  30.00   0.50    0.05    --   18.00  43.00-105.47   50
 75  ω    -45.00 -20.00   0.50    0.05    --  -30.00 -36.00-174.33   50
 76  ω     18.00  43.00   0.50    0.05    --   30.00  36.00  65.67   50
 77  ω    -47.00 -22.00   0.50    0.05    --  -34.00 -35.00  56.12   50
 78  ω    -27.00   4.00   0.50    0.05    --  -47.57  19.00-180.00   62
 79  ω     54.00  81.00   0.50    0.05    --   47.57 -99.00-150.00   54
 80  ω     18.00  44.00   0.50    0.05    --   47.57 -99.00-150.00   52
 81  ω    -70.00 -45.00   0.50    0.05    --  -58.00 -30.00 134.66   50
 82  ω   -128.00-102.00   0.50    0.20    --  -70.00 -29.00  62.41   52
 83  ω    -82.00 -57.00   0.50    0.20    --  -70.00 -29.00  62.41   50
 84  ω    -86.00 -61.00   0.50    0.20    --  -74.00 -29.00  20.48   50
 85  ω    -88.00 -62.00   0.50    0.20    --  -74.00 -29.00 -14.19   52
 86  ω    -43.00 -18.00   0.50    0.20    --  -86.25  37.00  60.00   50
 87  ω   -110.00 -84.00   0.50    0.20    --  -86.25 -28.00   9.61   52
 88  ω   -141.00-115.00   0.50    0.20    --  -86.25-125.00-150.00   52
 89  ω    153.00 178.00   0.50    0.20    --  107.11  19.00 -30.00   50
 90  ω     36.00  84.00   0.50    0.20    --  107.11 -99.00  90.00   96
 91  ω     96.00 122.00   0.50    0.20    --  107.11  19.00 -30.00   52
 92  ω    145.00 171.00   0.50    0.20    --  107.11  37.00-180.00   52
 93  ω     35.00  60.00   0.50    0.20    --  107.11 -57.00-180.00   50
 94  ω    114.00 140.00   0.50    0.20    --  107.11  37.00-180.00   52
 95  ω    108.00 135.00   0.50    0.20    --  107.11  19.00  60.00   54
 96  ω     35.00  78.00   0.50    0.20    --  107.11 -99.00 -60.00   86
 97  ω     35.00  60.00   0.50    0.20    --  107.11 -57.00 -90.00   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      -0.2402715000
_diffrn_orient_matrix_UB_12      0.1054064000
_diffrn_orient_matrix_UB_13      0.0191973000
_diffrn_orient_matrix_UB_21      -0.0203060000
_diffrn_orient_matrix_UB_22      -0.0227830000
_diffrn_orient_matrix_UB_23      0.1593447000
_diffrn_orient_matrix_UB_31      0.0814837000
_diffrn_orient_matrix_UB_32      0.1741924000
_diffrn_orient_matrix_UB_33      -0.0142668000
_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  0.0661
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11036
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.349
_diffrn_reflns_theta_min         4.625
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    6.167
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.781
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_description       needle
_exptl_crystal_F_000             244
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0400
_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)+(0.0421P)²+0.8944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1123
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1717
_reflns_number_total             1884
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt03260c1.cif
_cod_data_source_block           js1020v
_cod_depositor_comments
'Adding full bibliography for 7706457--7706460.cif.'
_cod_database_code               7706459
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C5H6N6O
_chemical_oxdiff_usercomment     YT7
_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   0.887
_shelx_estimated_absorpt_t_min   0.413
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3A)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id YT7
_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 1.902
_oxdiff_exptl_absorpt_empirical_full_min 0.613
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
Cl1 Cl -0.15739(10) 0.80871(9) 0.55082(7) 0.0175(2) Uani 1 1 d . . . . .
Cl2 Cl 0.25082(10) 0.19578(8) -0.02833(7) 0.0178(2) Uani 1 1 d . . . . .
O1 O 0.1390(3) 0.7941(3) 0.2719(2) 0.0183(4) Uani 1 1 d . . . . .
H1 H 0.055(8) 0.790(7) 0.364(5) 0.057(14) Uiso 1 1 d . . . . .
N1 N 0.3133(4) 0.6494(3) 0.2739(2) 0.0152(5) Uani 1 1 d . . . . .
N2 N 0.6523(4) 0.5257(3) 0.3444(2) 0.0168(5) Uani 1 1 d . . . . .
N3 N 0.8127(4) 0.2380(3) 0.2663(3) 0.0162(5) Uani 1 1 d . . . . .
H3 H 0.908(7) 0.209(5) 0.307(4) 0.025(10) Uiso 1 1 d . . . . .
N4 N 0.5794(4) 0.2190(3) 0.1458(2) 0.0153(5) Uani 1 1 d . . . . .
H4 H 0.514(5) 0.178(4) 0.097(3) 0.013(8) Uiso 1 1 d . . . . .
N5 N 0.4530(4) 0.8015(3) 0.3994(3) 0.0185(5) Uani 1 1 d . . . . .
H5A H 0.345(6) 0.889(5) 0.393(4) 0.021(9) Uiso 1 1 d . . . . .
H5B H 0.549(7) 0.802(5) 0.445(4) 0.034(11) Uiso 1 1 d . . . . .
N6 N 0.1606(4) 0.5274(3) 0.1337(3) 0.0175(5) Uani 1 1 d . . . . .
H6A H 0.051(6) 0.620(5) 0.137(4) 0.023(9) Uiso 1 1 d . . . . .
H6B H 0.171(7) 0.439(6) 0.081(4) 0.040(11) Uiso 1 1 d . . . . .
C1 C 0.4783(4) 0.6579(4) 0.3393(3) 0.0158(5) Uani 1 1 d . . . . .
C2 C 0.6565(4) 0.3927(4) 0.2753(3) 0.0144(5) Uani 1 1 d . . . . .
C3 C 0.7631(4) 0.1369(4) 0.1880(3) 0.0168(6) Uani 1 1 d . . . . .
H3A H 0.846876 0.023331 0.165985 0.020 Uiso 1 1 calc R U . . .
C4 C 0.5081(4) 0.3817(4) 0.1987(3) 0.0140(5) Uani 1 1 d . . . . .
C5 C 0.3194(4) 0.5176(4) 0.1976(3) 0.0152(5) 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'
Cl Cl 0.3639 0.7018 '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
0 1 6 0.0797
0 0 -6 0.0779
0 1 -1 0.0442
1 5 0 0.0221
0 -5 0 0.0243
-1 0 0 0.0102
1 0 0 0.0102
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
N1 O1 H1 105(3) . . ?
O1 N1 C1 118.0(2) . . ?
C5 N1 O1 116.3(2) . . ?
C5 N1 C1 125.3(2) . . ?
C1 N2 C2 113.5(2) . . ?
C2 N3 H3 125(3) . . ?
C3 N3 H3 125(3) . . ?
C3 N3 C2 109.0(2) . . ?
C3 N4 H4 126(2) . . ?
C3 N4 C4 107.6(2) . . ?
C4 N4 H4 126(2) . . ?
H5A N5 H5B 122(4) . . ?
C1 N5 H5A 121(2) . . ?
C1 N5 H5B 117(3) . . ?
H6A N6 H6B 121(4) . . ?
C5 N6 H6A 120(2) . . ?
C5 N6 H6B 119(3) . . ?
N2 C1 N1 121.8(2) . . ?
N5 C1 N1 117.3(2) . . ?
N5 C1 N2 120.9(3) . . ?
N2 C2 N3 126.0(2) . . ?
N2 C2 C4 127.8(2) . . ?
N3 C2 C4 106.2(2) . . ?
N3 C3 H3A 125.1 . . ?
N4 C3 N3 109.8(2) . . ?
N4 C3 H3A 125.1 . . ?
N4 C4 C5 133.6(3) . . ?
C2 C4 N4 107.4(2) . . ?
C2 C4 C5 118.8(2) . . ?
N1 C5 C4 112.4(2) . . ?
N6 C5 N1 120.5(2) . . ?
N6 C5 C4 127.1(3) . . ?
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 H1 0.94(5) . ?
O1 N1 1.385(3) . ?
N1 C1 1.391(4) . ?
N1 C5 1.371(4) . ?
N2 C1 1.329(4) . ?
N2 C2 1.335(4) . ?
N3 H3 0.78(4) . ?
N3 C2 1.370(4) . ?
N3 C3 1.340(4) . ?
N4 H4 0.85(4) . ?
N4 C3 1.326(4) . ?
N4 C4 1.392(3) . ?
N5 H5A 0.85(4) . ?
N5 H5B 0.85(5) . ?
N5 C1 1.321(4) . ?
N6 H6A 0.88(4) . ?
N6 H6B 0.91(5) . ?
N6 C5 1.309(4) . ?
C2 C4 1.384(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.403(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 Cl1 0.94(5) 2.01(5) 2.944(2) 172(4) . yes
N4 H4 Cl2 0.85(4) 2.30(4) 3.095(2) 154(3) . yes
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 C1 N2 -179.2(2) . . . . ?
O1 N1 C1 N5 2.3(4) . . . . ?
O1 N1 C5 N6 -3.5(4) . . . . ?
O1 N1 C5 C4 176.4(2) . . . . ?
N2 C2 C4 N4 -180.0(3) . . . . ?
N2 C2 C4 C5 -4.7(4) . . . . ?
N3 C2 C4 N4 0.2(3) . . . . ?
N3 C2 C4 C5 175.4(2) . . . . ?
N4 C4 C5 N1 175.2(3) . . . . ?
N4 C4 C5 N6 -4.9(5) . . . . ?
C1 N1 C5 N6 -176.2(3) . . . . ?
C1 N1 C5 C4 3.7(4) . . . . ?
C1 N2 C2 N3 -178.1(3) . . . . ?
C1 N2 C2 C4 2.1(4) . . . . ?
C2 N2 C1 N1 3.4(4) . . . . ?
C2 N2 C1 N5 -178.2(3) . . . . ?
C2 N3 C3 N4 -0.3(3) . . . . ?
C2 C4 C5 N1 1.5(4) . . . . ?
C2 C4 C5 N6 -178.6(3) . . . . ?
C3 N3 C2 N2 -179.8(3) . . . . ?
C3 N3 C2 C4 0.0(3) . . . . ?
C3 N4 C4 C2 -0.4(3) . . . . ?
C3 N4 C4 C5 -174.6(3) . . . . ?
C4 N4 C3 N3 0.5(3) . . . . ?
C5 N1 C1 N2 -6.7(4) . . . . ?
C5 N1 C1 N5 174.9(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168343826
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
0.2899 0.7423 6.3528 0.1305 0.9895 0.0623
0.0772 0.0674 -6.1674 -0.1298 -0.9859 0.1060
0.0009 0.9998 -0.9998 0.0860 -0.1821 0.1885
0.8838 5.0279 0.3505 0.3244 -0.0766 0.9428
0.0436 -4.8607 0.0891 -0.5211 0.1241 -0.8444
-1.0010 0.0005 0.0022 0.2406 0.0207 -0.0815
1.0010 -0.0005 -0.0022 -0.2406 -0.0207 0.0815
