# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_js1020s
_database_code_depnum_ccdc_archive 'CCDC 2040720'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;
_audit_creation_date             2020-10-20
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.10.11 svn.r5b043f8a for OlexSys, GUI svn.r6175)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H5 N6 O, N O3'
_chemical_formula_sum            'C4 H5 N7 O4'
_chemical_formula_weight         215.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4H5N7O4
_chemical_oxdiff_usercomment     YT3
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   6.1448(3)
_cell_length_b                   16.4016(6)
_cell_length_c                   7.6331(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.289(3)
_cell_angle_gamma                90
_cell_volume                     768.68(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2118
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.9850
_cell_measurement_theta_min      5.3640
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.804
_exptl_absorpt_coefficient_mu    1.452
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.799
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0764
0 0 1 0.0764
-1 -1 0 0.0468
1 1 0 0.0368
0 -1 0 0.0357
0 1 0 0.0027

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.038
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
-0.0000 -0.0000 -1.0000 0.0562 0.1418 0.1324
0.0000 0.0000 1.0000 -0.0562 -0.1418 -0.1324
-1.0000 -1.0000 0.0000 0.0586 -0.1832 0.1864
1.0000 1.0000 -0.0000 -0.0586 0.1832 -0.1864
0.0000 -1.0000 0.0000 -0.0756 -0.0190 0.0524
-0.0000 1.0000 -0.0000 0.0756 0.0190 -0.0524

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus operating at  100 K.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structure was solved 
by the direct method using the SHELXT program and refined by least squares 
method on F2, SHELXL, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4461
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.136
_diffrn_reflns_theta_min         5.394
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  25.00   0.50    0.18    --  -47.57  76.00  77.00  130
  2  ω     48.00  73.00   0.50    0.18    --   47.57  76.00  77.00   50
  3  ω     90.00 164.00   0.50    0.72    --  107.11  76.00  77.00  148
  4  ω    135.00 172.00   0.50    0.72    --  107.11  77.00 -60.00   74
  5  ω    128.00 173.00   0.50    0.72    --  107.11  57.00-180.00   90
  6  ω     39.00  64.00   0.50    0.72    --  107.11 -57.00 -30.00   50
  7  ω     35.00  84.00   0.50    0.72    --  107.11 -76.00 -49.00   98
  8  ω     36.00  64.00   0.50    0.72    --  107.11 -57.00   0.00   56
  9  ω     38.00  64.00   0.50    0.72    --  107.11 -57.00  30.00   52
 10  ω     36.00  62.00   0.50    0.72    --  107.11 -57.00  90.00   52
 11  ω     38.00  63.00   0.50    0.72    --  107.11 -57.00 150.00   50
 12  ω     38.00  64.00   0.50    0.72    --  107.11 -57.00 120.00   52
 13  ω     -1.00  24.00   0.50    0.18    --   47.57 -76.00 -49.00   50
 14  ω    -26.00  25.00   0.50    0.18    --   47.57 -19.00 -60.00  102
 15  ω     38.00 105.00   0.50    0.72    --  107.11-125.00 -60.00  134
 16  ω    -80.00 -54.00   0.50    0.18    --  -47.57 125.00-120.00   52
 17  ω    -42.00 -17.00   0.50    0.72    --  -86.25  37.00 -90.00   50
 18  ω   -103.00 -28.00   0.50    0.18    --  -47.57 -76.00 -49.00  150
 19  ω    -87.00 -38.00   0.50    0.72    --  -86.25  76.00  77.00   98
 20  ω   -136.00-111.00   0.50    0.72    --  -86.25 -76.00 -49.00   50
 21  ω   -147.00-121.00   0.50    0.72    --  -86.25 -37.00  30.00   52
 22  ω   -153.00-128.00   0.50    0.72    --  -86.25 -57.00  30.00   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      -0.1342542000
_diffrn_orient_matrix_UB_12      0.0756142000
_diffrn_orient_matrix_UB_13      -0.0561734000
_diffrn_orient_matrix_UB_21      0.1641773000
_diffrn_orient_matrix_UB_22      0.0189814000
_diffrn_orient_matrix_UB_23      -0.1418342000
_diffrn_orient_matrix_UB_31      -0.1339806000
_diffrn_orient_matrix_UB_32      -0.0524106000
_diffrn_orient_matrix_UB_33      -0.1324088000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1336
_reflns_number_total             1526
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1526
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.069
_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)+(0.0665P)²+0.1782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1140
_refine_special_details          
;
The structure was refined by Least Squares using version 2018/2 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.35320(19) 0.07493(7) 0.54275(14) 0.0184(3) Uani 1 1 d . . . . .
N1 N 0.3376(2) 0.27873(9) 0.66588(18) 0.0166(3) Uani 1 1 d . . . . .
H1 H 0.337(5) 0.3154(17) 0.574(4) 0.044(7) Uiso 1 1 d . . . . .
N2 N 0.3384(2) 0.25533(8) 0.97727(18) 0.0159(3) Uani 1 1 d . . . . .
N3 N 0.3457(2) 0.15700(9) 0.49095(18) 0.0172(3) Uani 1 1 d . . . . .
N4 N 0.3514(2) 0.06703(9) 0.72189(17) 0.0173(3) Uani 1 1 d . . . . .
N5 N 0.3393(2) 0.38408(9) 0.8628(2) 0.0175(3) Uani 1 1 d . . . . .
H5A H 0.347(4) 0.4196(16) 0.776(4) 0.030(6) Uiso 1 1 d . . . . .
H5B H 0.343(4) 0.3991(14) 0.965(4) 0.025(6) Uiso 1 1 d . . . . .
N6 N 0.3310(2) 0.12642(9) 1.09405(18) 0.0172(3) Uani 1 1 d . . . . .
H6A H 0.325(4) 0.0714(15) 1.078(3) 0.024(5) Uiso 1 1 d . . . . .
H6B H 0.332(3) 0.1496(14) 1.199(3) 0.021(5) Uiso 1 1 d . . . . .
C1 C 0.3417(2) 0.19656(10) 0.6388(2) 0.0152(4) Uani 1 1 d . . . . .
C2 C 0.3441(2) 0.14159(10) 0.7803(2) 0.0146(3) Uani 1 1 d . . . . .
C3 C 0.3376(2) 0.17509(10) 0.9580(2) 0.0144(3) Uani 1 1 d . . . . .
C4 C 0.3388(2) 0.30547(10) 0.8360(2) 0.0148(3) Uani 1 1 d . . . . .
O2 O 0.3693(2) 0.35036(7) 0.34875(15) 0.0202(3) Uani 1 1 d . . . . .
O3 O 0.2736(2) 0.45887(7) 0.48933(15) 0.0196(3) Uani 1 1 d . . . . .
O4 O 0.3555(2) 0.46744(7) 0.21549(15) 0.0205(3) Uani 1 1 d . . . . .
N7 N 0.3339(2) 0.42605(8) 0.35030(18) 0.0152(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 N3 1.4033(18) . ?
O1 N4 1.3739(18) . ?
N1 H1 0.93(3) . ?
N1 C1 1.364(2) . ?
N1 C4 1.370(2) . ?
N2 C3 1.324(2) . ?
N2 C4 1.356(2) . ?
N3 C1 1.303(2) . ?
N4 C2 1.303(2) . ?
N5 H5A 0.88(3) . ?
N5 H5B 0.81(3) . ?
N5 C4 1.306(2) . ?
N6 H6A 0.91(2) . ?
N6 H6B 0.89(2) . ?
N6 C3 1.312(2) . ?
C1 C2 1.407(2) . ?
C2 C3 1.465(2) . ?
O2 N7 1.2605(19) . ?
O3 N7 1.2588(18) . ?
O4 N7 1.2444(18) . ?

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
N4 O1 N3 111.68(12) . . ?
C1 N1 H1 121.7(17) . . ?
C1 N1 C4 117.41(14) . . ?
C4 N1 H1 120.9(17) . . ?
C3 N2 C4 120.95(14) . . ?
C1 N3 O1 103.60(12) . . ?
C2 N4 O1 104.70(13) . . ?
H5A N5 H5B 121(2) . . ?
C4 N5 H5A 122.3(16) . . ?
C4 N5 H5B 116.6(16) . . ?
H6A N6 H6B 123(2) . . ?
C3 N6 H6A 120.0(15) . . ?
C3 N6 H6B 117.1(15) . . ?
N1 C1 C2 121.11(14) . . ?
N3 C1 N1 128.65(15) . . ?
N3 C1 C2 110.24(15) . . ?
N4 C2 C1 109.78(14) . . ?
N4 C2 C3 132.15(15) . . ?
C1 C2 C3 118.07(15) . . ?
N2 C3 C2 118.38(14) . . ?
N6 C3 N2 121.12(15) . . ?
N6 C3 C2 120.50(15) . . ?
N2 C4 N1 124.01(15) . . ?
N5 C4 N1 117.67(15) . . ?
N5 C4 N2 118.32(15) . . ?
O3 N7 O2 119.07(13) . . ?
O4 N7 O2 120.35(13) . . ?
O4 N7 O3 120.57(13) . . ?

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
N1 H1 O2 0.93(3) 1.83(3) 2.7047(19) 157(3) . yes
N6 H6A O3 0.91(2) 2.00(2) 2.8875(19) 163(2) 2_546 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 N3 C1 N1 178.79(14) . . . . ?
O1 N3 C1 C2 -0.61(16) . . . . ?
O1 N4 C2 C1 -0.12(17) . . . . ?
O1 N4 C2 C3 179.63(16) . . . . ?
N1 C1 C2 N4 -178.96(13) . . . . ?
N1 C1 C2 C3 1.3(2) . . . . ?
N3 O1 N4 C2 -0.26(17) . . . . ?
N3 C1 C2 N4 0.50(19) . . . . ?
N3 C1 C2 C3 -179.29(14) . . . . ?
N4 O1 N3 C1 0.55(16) . . . . ?
N4 C2 C3 N2 177.65(16) . . . . ?
N4 C2 C3 N6 -2.4(3) . . . . ?
C1 N1 C4 N2 -1.7(2) . . . . ?
C1 N1 C4 N5 178.69(14) . . . . ?
C1 C2 C3 N2 -2.6(2) . . . . ?
C1 C2 C3 N6 177.34(14) . . . . ?
C3 N2 C4 N1 0.3(2) . . . . ?
C3 N2 C4 N5 179.90(14) . . . . ?
C4 N1 C1 N3 -178.54(15) . . . . ?
C4 N1 C1 C2 0.8(2) . . . . ?
C4 N2 C3 N6 -178.06(14) . . . . ?
C4 N2 C3 C2 1.9(2) . . . . ?

_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 YT3
_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 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.756
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_js920g
_database_code_depnum_ccdc_archive 'CCDC 2040723'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;
_audit_creation_date             2020-10-07
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H4 N6 O2, H2 O'
_chemical_formula_sum            'C4 H6 N6 O3'
_chemical_formula_weight         186.15
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4H4N6O2
_chemical_oxdiff_usercomment     YT2
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'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x+1/2, z+1/2'
'-x+1/2, -y+1/2, z'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'y, -x-1/2, -z-1/2'
'x-1/2, y-1/2, -z'
'-y-1/2, x, -z-1/2'

_cell_length_a                   14.9237(4)
_cell_length_b                   14.9237(4)
_cell_length_c                   7.6656(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1707.26(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3068
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      75.6950
_cell_measurement_theta_min      5.9210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus operating at  100 K.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structure was solved 
by the direct method using the SHELXT program and refined by least squares 
method on F2, SHELXL, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9080
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.434
_diffrn_reflns_theta_min         4.189
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_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 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  12.00   0.50    2.27    --  -47.45  19.00 -60.00   52
  2  ω    -27.00  28.00   0.50    2.27    --  -47.45  19.00 120.00  110
  3  ω     52.00  85.00   0.50    2.27    --   47.45-116.00  11.00   66
  4  ω     35.00  60.00   0.50    9.08    --  107.74 -57.00  30.00   50
  5  ω     36.00  63.00   0.50    9.08    --  107.74 -57.00  60.00   54
  6  ω     37.00  62.00   0.50    9.08    --  107.74 -57.00   0.00   50
  7  ω     43.00 105.00   0.50    9.08    --  107.74-116.00  11.00  124
  8  ω     37.00  62.00   0.50    9.08    --  107.74 -57.00-120.00   50
  9  ω     36.00  62.00   0.50    9.08    --  107.74 -57.00 -90.00   52
 10  ω     38.00  64.00   0.50    9.08    --  107.74 -57.00-150.00   52
 11  ω     58.00 100.00   0.50    9.08    --  107.74 -99.00-180.00   84
 12  ω    134.00 167.00   0.50    9.08    --  107.74  49.00-128.00   66
 13  ω    126.00 171.00   0.50    9.08    --  107.74  77.00 -60.00   90
 14  ω    133.00 159.00   0.50    9.08    --  107.74  57.00 -90.00   52
 15  ω     95.00 128.00   0.50    9.08    --  107.74  49.00-128.00   66
 16  ω    130.00 157.00   0.50    9.08    --  107.74  77.00  60.00   54
 17  ω    134.00 176.00   0.50    9.08    --  107.74  77.00 120.00   84
 18  ω    127.00 169.00   0.50    9.08    --  107.74  57.00 150.00   84
 19  ω    -20.00   7.00   0.50    2.27    --   47.45 -19.00-120.00   54
 20  ω   -113.00 -50.00   0.50    2.27    --  -47.45-163.00-137.00  126
 21  ω   -154.00-111.00   0.50    9.08    --  -86.25 -49.00  83.00   86
 22  ω    -71.00 -45.00   0.50    9.08    --  -86.25 163.00-111.00   52
 23  ω   -107.00 -80.00   0.50    9.08    --  -86.25 -49.00  83.00   54
;
_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      0.0570697000
_diffrn_orient_matrix_UB_12      -0.0638222000
_diffrn_orient_matrix_UB_13      -0.1123637000
_diffrn_orient_matrix_UB_21      -0.0240428000
_diffrn_orient_matrix_UB_22      0.0547188000
_diffrn_orient_matrix_UB_23      -0.1639212000
_diffrn_orient_matrix_UB_31      0.0826085000
_diffrn_orient_matrix_UB_32      0.0598780000
_diffrn_orient_matrix_UB_33      0.0299078000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1559
_reflns_number_total             1775
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution    
'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1775
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0613
_refine_ls_restrained_S_all      1.144
_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)+(0.0465P)²+2.3728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1497
_refine_special_details          
;
The structure was refined by Least Squares using version 2018/2 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_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 Riding coordinates:
 N5(H5A,H5B), N6(H6A,H6B), O1W(H1WA,H1WB)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.59526(17) 0.56155(17) -0.0457(2) 0.0550(8) Uani 1 1 d . . . . .
O2 O 0.42018(11) 0.73799(11) -0.60307(19) 0.0228(4) Uani 1 1 d . . . . .
N1 N 0.45066(13) 0.70920(13) -0.4481(2) 0.0210(5) Uani 1 1 d . . . . .
N2 N 0.43182(13) 0.72043(13) -0.1354(2) 0.0228(5) Uani 1 1 d . . . . .
N3 N 0.53155(17) 0.62241(17) 0.0149(3) 0.0381(6) Uani 1 1 d . . . . .
N4 N 0.59921(19) 0.5591(2) -0.2255(3) 0.0487(8) Uani 1 1 d . . . . .
N5 N 0.34957(13) 0.80606(13) -0.3291(2) 0.0214(5) Uani 1 1 d . . . . .
H5A H 0.321934 0.832543 -0.245229 0.026 Uiso 1 1 d R U . . .
H5B H 0.338044 0.820273 -0.435499 0.026 Uiso 1 1 d R U . . .
N6 N 0.54267(16) 0.61093(16) -0.5932(3) 0.0328(6) Uani 1 1 d . . . . .
H6A H 0.523616 0.631693 -0.691034 0.039 Uiso 1 1 d R U . . .
H6B H 0.581306 0.568143 -0.591884 0.039 Uiso 1 1 d R U . . .
C1 C 0.41050(15) 0.74547(15) -0.2970(3) 0.0210(5) Uani 1 1 d . . . . .
C2 C 0.49687(17) 0.65724(17) -0.1281(3) 0.0262(6) Uani 1 1 d . . . . .
C3 C 0.53899(18) 0.61720(19) -0.2739(3) 0.0314(6) Uani 1 1 d . . . . .
C4 C 0.51198(17) 0.64424(17) -0.4472(3) 0.0262(6) Uani 1 1 d . . . . .
O1W O 0.34915(12) 0.53421(13) -0.3654(2) 0.0313(5) Uani 1 1 d . . . . .
H1WA H 0.314198 0.535859 -0.277864 0.047 Uiso 1 1 d R U . . .
H1WB H 0.318658 0.556869 -0.448154 0.047 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 N3 1.394(3) . ?
O1 N4 1.381(3) . ?
O2 N1 1.342(2) . ?
N1 C1 1.412(3) . ?
N1 C4 1.333(3) . ?
N2 C1 1.333(3) . ?
N2 C2 1.355(3) . ?
N3 C2 1.319(3) . ?
N4 C3 1.302(3) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8602 . ?
N5 C1 1.306(3) . ?
N6 H6A 0.8596 . ?
N6 H6B 0.8605 . ?
N6 C4 1.308(3) . ?
C2 C3 1.415(3) . ?
C3 C4 1.446(3) . ?
O1W H1WA 0.8503 . ?
O1W H1WB 0.8507 . ?

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
N4 O1 N3 112.26(18) . . ?
O2 N1 C1 117.34(19) . . ?
C4 N1 O2 118.06(19) . . ?
C4 N1 C1 124.4(2) . . ?
C1 N2 C2 113.9(2) . . ?
C2 N3 O1 104.3(2) . . ?
C3 N4 O1 103.7(2) . . ?
H5A N5 H5B 120.0 . . ?
C1 N5 H5A 120.8 . . ?
C1 N5 H5B 119.2 . . ?
H6A N6 H6B 120.0 . . ?
C4 N6 H6A 119.6 . . ?
C4 N6 H6B 120.4 . . ?
N2 C1 N1 123.6(2) . . ?
N5 C1 N1 114.0(2) . . ?
N5 C1 N2 122.4(2) . . ?
N2 C2 C3 125.4(2) . . ?
N3 C2 N2 126.2(2) . . ?
N3 C2 C3 108.4(2) . . ?
N4 C3 C2 111.3(2) . . ?
N4 C3 C4 129.8(2) . . ?
C2 C3 C4 119.0(2) . . ?
N1 C4 C3 113.6(2) . . ?
N6 C4 N1 120.8(2) . . ?
N6 C4 C3 125.7(2) . . ?
H1WA O1W H1WB 104.4 . . ?

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
N5 H5A O2 0.86 1.92 2.759(2) 163.6 2_655 yes
N6 H6A N3 0.86 2.26 3.013(3) 146.1 1_554 yes
N6 H6B O1W 0.86 1.88 2.720(3) 166.7 5_664 yes
O1W H1WA O2 0.85 1.88 2.694(2) 161.0 4_465 yes
O1W H1WB N2 0.85 2.06 2.869(3) 159.0 4_464 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 N3 C2 N2 -179.8(3) . . . . ?
O1 N3 C2 C3 0.4(3) . . . . ?
O1 N4 C3 C2 0.4(4) . . . . ?
O1 N4 C3 C4 -179.9(3) . . . . ?
O2 N1 C1 N2 177.4(2) . . . . ?
O2 N1 C1 N5 -2.3(3) . . . . ?
O2 N1 C4 N6 1.3(4) . . . . ?
O2 N1 C4 C3 -179.0(2) . . . . ?
N2 C2 C3 N4 179.7(3) . . . . ?
N2 C2 C3 C4 -0.1(4) . . . . ?
N3 O1 N4 C3 -0.1(4) . . . . ?
N3 C2 C3 N4 -0.5(4) . . . . ?
N3 C2 C3 C4 179.8(3) . . . . ?
N4 O1 N3 C2 -0.2(4) . . . . ?
N4 C3 C4 N1 -176.9(3) . . . . ?
N4 C3 C4 N6 2.8(5) . . . . ?
C1 N1 C4 N6 176.4(2) . . . . ?
C1 N1 C4 C3 -3.8(3) . . . . ?
C1 N2 C2 N3 178.5(3) . . . . ?
C1 N2 C2 C3 -1.7(4) . . . . ?
C2 N2 C1 N1 0.8(3) . . . . ?
C2 N2 C1 N5 -179.6(2) . . . . ?
C2 C3 C4 N1 2.8(4) . . . . ?
C2 C3 C4 N6 -177.5(3) . . . . ?
C4 N1 C1 N2 2.2(4) . . . . ?
C4 N1 C1 N5 -177.4(2) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.250 0.250 -0.896 152.9 47.2 '2 CH3CN'
2 0.750 0.750 -0.200 152.9 47.2 '2 CH3CN'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 YT2
_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 1.556
_oxdiff_exptl_absorpt_empirical_full_min 0.499
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_js1020v
_database_code_depnum_ccdc_archive 'CCDC 2040722'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;
_audit_creation_date             2020-10-26
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.10.11 svn.r5b043f8a for OlexSys, GUI svn.r6175)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl), C5 H8 N6 O'
_chemical_formula_sum            'C5 H8 Cl2 N6 O'
_chemical_formula_weight         239.07
_chemical_melting_point          ?
_chemical_oxdiff_formula         C5H6N6O
_chemical_oxdiff_usercomment     YT7
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3903(2)
_cell_length_b                   7.8053(2)
_cell_length_c                   9.9575(2)
_cell_angle_alpha                79.811(2)
_cell_angle_beta                 75.385(2)
_cell_angle_gamma                76.143(2)
_cell_volume                     463.01(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5784
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.7140
_cell_measurement_theta_min      8.3850
_shelx_estimated_absorpt_T_max   0.887
_shelx_estimated_absorpt_T_min   0.413
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             244
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

_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
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

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus operating at  100 K.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structure was solved 
by the direct method using the SHELXT program and refined by least squares 
method on F2, SHELXL, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1717
_reflns_number_total             1884
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.136
_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
_refine_special_details          
;
The structure was refined by Least Squares using version 2018/2 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_js920f_y
_database_code_depnum_ccdc_archive 'CCDC 2040721'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2020-11-03 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;
_audit_creation_date             2020-11-02
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.10.28 svn.r5b043f8a for OlexSys, GUI svn.r6176)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C4 H6 N7 O, 2(H2 O)'
_chemical_formula_sum            'C4 H10 Cl N7 O3'
_chemical_formula_weight         239.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4H5N7O
_chemical_oxdiff_usercomment     'YT5 '
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   8.3157(4)
_cell_length_b                   9.2267(4)
_cell_length_c                   12.9583(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.961(4)
_cell_angle_gamma                90
_cell_volume                     988.87(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4640
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9140
_cell_measurement_theta_min      5.8740
_shelx_estimated_absorpt_T_max   0.835
_shelx_estimated_absorpt_T_min   0.519
_exptl_absorpt_coefficient_mu    3.531
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.579
_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_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 1 0.0255
-2 0 -1 0.0275
-2 -5 5 0.1087
2 4 -5 0.0938
0 3 7 0.0785
0 -3 -7 0.0661
0 6 -3 0.0987
0 -6 3 0.1055
3 0 6 0.0468
-4 2 5 0.0549
5 -2 -4 0.0570
3 0 -7 0.0704
-2 4 -5 0.0780

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.053
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
2.0000 -0.0000 1.0000 0.1209 -0.3265 -0.2020
-2.0000 0.0000 -1.0000 -0.1209 0.3265 0.2020
-1.7508 -4.5105 5.0394 -0.1621 0.5436 -0.8235
2.2891 4.4667 -4.6311 0.1880 -0.6315 0.7522
0.0455 3.3776 6.9092 -0.7968 -0.5470 -0.2565
-0.2283 -2.6515 -7.4622 0.7584 0.5204 0.3926
-0.0653 5.6292 -2.8182 -0.2757 -0.4518 0.8484
0.0622 -5.6318 2.8089 0.2763 0.4528 -0.8477
3.1863 0.1144 6.2415 -0.1629 -0.6737 -0.7208
-4.0000 2.0000 5.0000 -0.9327 0.2440 -0.0038
5.0000 -2.0000 -4.0000 0.9559 -0.4226 -0.1414
3.0000 0.0000 -7.0000 0.8136 -0.2295 0.4490
-2.0000 4.0000 -5.0000 -0.1637 0.0598 0.9789

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus operating at  100 K.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structure was solved 
by the direct method using the SHELXT program and refined by least squares 
method on F2, SHELXL, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11264
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.347
_diffrn_reflns_theta_min         5.898
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     50.00  75.00   0.50    0.05    --   47.45  68.00 115.00   50
  2  ω     89.00 130.00   0.50    0.16    --  107.11  68.00 115.00   82
  3  ω    137.00 174.00   0.50    0.16    --  107.11  57.00 150.00   74
  4  ω    137.00 170.00   0.50    0.16    --  107.11  68.00 115.00   66
  5  ω    128.00 158.00   0.50    0.16    --  107.11  57.00 -30.00   60
  6  ω    140.00 168.00   0.50    0.16    --  107.11  57.00-150.00   56
  7  ω    142.00 168.00   0.50    0.16    --  107.11  37.00-120.00   52
  8  ω    114.00 141.00   0.50    0.16    --  107.11  37.00-120.00   54
  9  ω     95.00 139.00   0.50    0.16    --  107.11  19.00-150.00   88
 10  ω    117.00 147.00   0.50    0.16    --  107.11  37.00-150.00   60
 11  ω     95.00 135.00   0.50    0.16    --  107.11  19.00 -60.00   80
 12  ω    114.00 178.00   0.50    0.16    --  107.11  37.00   0.00  128
 13  ω    123.00 178.00   0.50    0.16    --  107.11  37.00  30.00  110
 14  ω     97.00 174.00   0.50    0.16    --  107.11  19.00  90.00  154
 15  ω    -41.00 -16.00   0.50    0.16    --  -86.25  37.00 -60.00   50
 16  ω    -56.00 -30.00   0.50    0.05    --  -47.45 125.00-150.00   52
 17  ω    -79.00 -18.00   0.50    0.16    --  -86.25  68.00 115.00  122
 18  ω   -157.00-132.00   0.50    0.16    --  -86.25 -77.00 -60.00   50
 19  ω   -156.00-130.00   0.50    0.16    --  -86.25 -37.00 -60.00   52
 20  ω   -119.00 -88.00   0.50    0.16    --  -86.25 -30.00-148.73   62
 21  ω   -112.00 -28.00   0.50    0.05    --  -47.45 -68.00 -18.00  168
 22  ω   -117.00 -84.00   0.50    0.16    --  -86.25 -29.00-171.90   66
 23  ω   -131.00 -90.00   0.50    0.16    --  -86.25 -68.00 -18.00   82
 24  ω   -109.00 -80.00   0.50    0.16    --  -86.25 -29.00 169.72   58
 25  ω   -155.00 -75.00   0.50    0.16    --  -86.25 -26.00 137.18  160
 26  ω   -141.00-116.00   0.50    0.16    --  -86.25 -29.00 169.72   50
 27  ω   -159.00-133.00   0.50    0.16    --  -86.25 -77.00 120.00   52
 28  ω   -105.00 -77.00   0.50    0.16    --  -86.25 -24.00-141.79   56
 29  ω    -27.00  26.00   0.50    0.05    --  -47.45  19.00 120.00  106
 30  ω    -14.00  16.00   0.50    0.05    --  -47.45  68.00 115.00   60
 31  ω    -64.00 -26.00   0.50    0.05    --  -47.45  68.00 115.00   76
 32  ω    -61.00  15.00   0.50    0.05    --  -47.45  57.00 -30.00  152
 33  ω     52.00  95.00   0.50    0.16    --  107.11 -99.00  60.00   86
 34  ω     35.00  63.00   0.50    0.16    --  107.11 -57.00  30.00   56
 35  ω     39.00  96.00   0.50    0.16    --  107.11 -77.00 -30.00  114
 36  ω     69.00  95.00   0.50    0.16    --  107.11 -77.00  30.00   52
 37  ω     43.00  76.00   0.50    0.16    --  107.11 -68.00 -18.00   66
 38  ω     35.00  60.00   0.50    0.16    --  107.11 -57.00 120.00   50
 39  ω     38.00  63.00   0.50    0.16    --  107.11 -57.00 150.00   50
 40  ω     38.00  63.00   0.50    0.16    --  107.11 -57.00   0.00   50
 41  ω     14.00  39.00   0.50    0.05    --   47.45 -68.00 -18.00   50
 42  ω     36.00  65.00   0.50    0.16    --  107.11 -57.00-150.00   58
 43  ω     35.00  60.00   0.50    0.16    --  107.11 -57.00-180.00   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      0.0976490000
_diffrn_orient_matrix_UB_12      -0.0850789000
_diffrn_orient_matrix_UB_13      -0.0743834000
_diffrn_orient_matrix_UB_21      -0.1479510000
_diffrn_orient_matrix_UB_22      -0.0973138000
_diffrn_orient_matrix_UB_23      -0.0306276000
_diffrn_orient_matrix_UB_31      -0.0567468000
_diffrn_orient_matrix_UB_32      0.1057762000
_diffrn_orient_matrix_UB_33      -0.0884595000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1862
_reflns_number_total             2044
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2044
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0625P)²+0.6790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1168
_refine_special_details          
;
The structure was refined by Least Squares using version 2018/2 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.97380(6) 0.50323(5) 0.75754(4) 0.02559(19) Uani 1 1 d . . . . .
O1 O 0.65588(18) 0.24081(15) 0.54839(11) 0.0243(3) Uani 1 1 d . . . . .
N1 N 0.6687(2) 0.38857(17) 0.56148(13) 0.0212(4) Uani 1 1 d . . . . .
N2 N 0.5867(2) 0.59272(18) 0.65623(13) 0.0225(4) Uani 1 1 d . . . . .
N3 N 0.6896(2) 0.81267(19) 0.58587(14) 0.0236(4) Uani 1 1 d . . . . .
H3 H 0.650(3) 0.880(3) 0.624(2) 0.028(6) Uiso 1 1 d . . . . .
N4 N 0.7814(2) 0.84635(19) 0.50802(13) 0.0252(4) Uani 1 1 d . . . . .
N5 N 0.8197(2) 0.72684(18) 0.46226(13) 0.0237(4) Uani 1 1 d . . . . .
N6 N 0.8197(2) 0.3934(2) 0.42133(14) 0.0244(4) Uani 1 1 d . . . . .
H6A H 0.812(3) 0.301(3) 0.410(2) 0.034(7) Uiso 1 1 d . . . . .
H6B H 0.872(3) 0.441(3) 0.376(2) 0.034(7) Uiso 1 1 d . . . . .
N7 N 0.5237(2) 0.3586(2) 0.70227(14) 0.0252(4) Uani 1 1 d . . . . .
H7A H 0.528(4) 0.261(4) 0.694(2) 0.048(8) Uiso 1 1 d . . . . .
H7B H 0.468(4) 0.393(3) 0.750(2) 0.040(8) Uiso 1 1 d . . . . .
C1 C 0.7523(2) 0.4631(2) 0.49335(14) 0.0208(4) Uani 1 1 d . . . . .
C2 C 0.5921(2) 0.4498(2) 0.64219(15) 0.0218(4) Uani 1 1 d . . . . .
C3 C 0.6690(2) 0.6680(2) 0.59020(15) 0.0214(4) Uani 1 1 d . . . . .
C4 C 0.7518(2) 0.6149(2) 0.51116(15) 0.0207(4) Uani 1 1 d . . . . .
O2 O 0.8136(2) 0.09775(16) 0.36285(13) 0.0262(3) Uani 1 1 d . . . . .
H2A H 0.725(4) 0.079(3) 0.332(2) 0.034(7) Uiso 1 1 d . . . . .
H2B H 0.835(4) 0.038(4) 0.408(3) 0.057(10) Uiso 1 1 d . . . . .
O3 O 0.57923(19) 0.65435(17) 0.86555(12) 0.0265(3) Uani 1 1 d . . . . .
H3A H 0.504(3) 0.712(3) 0.874(2) 0.027(7) Uiso 1 1 d . . . . .
H3B H 0.557(5) 0.647(4) 0.794(3) 0.074(12) Uiso 1 1 d . . . . .
H1 H 0.747(4) 0.202(4) 0.583(3) 0.052(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 1.377(2) . ?
O1 H1 0.91(4) . ?
N1 C1 1.365(3) . ?
N1 C2 1.399(3) . ?
N2 C2 1.332(3) . ?
N2 C3 1.343(3) . ?
N3 H3 0.88(3) . ?
N3 N4 1.363(2) . ?
N3 C3 1.348(3) . ?
N4 N5 1.307(2) . ?
N5 C4 1.364(3) . ?
N6 H6A 0.87(3) . ?
N6 H6B 0.88(3) . ?
N6 C1 1.307(3) . ?
N7 H7A 0.91(3) . ?
N7 H7B 0.87(3) . ?
N7 C2 1.315(3) . ?
C1 C4 1.420(3) . ?
C3 C4 1.382(3) . ?
O2 H2A 0.82(3) . ?
O2 H2B 0.81(4) . ?
O3 H3A 0.84(3) . ?
O3 H3B 0.92(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
N1 O1 H1 106(2) . . ?
O1 N1 C2 117.19(16) . . ?
C1 N1 O1 117.20(16) . . ?
C1 N1 C2 125.59(17) . . ?
C2 N2 C3 113.46(16) . . ?
N4 N3 H3 121.8(18) . . ?
C3 N3 H3 128.3(18) . . ?
C3 N3 N4 109.89(17) . . ?
N5 N4 N3 108.98(16) . . ?
N4 N5 C4 107.18(16) . . ?
H6A N6 H6B 114(3) . . ?
C1 N6 H6A 125.0(19) . . ?
C1 N6 H6B 120.6(19) . . ?
H7A N7 H7B 119(3) . . ?
C2 N7 H7A 122(2) . . ?
C2 N7 H7B 119(2) . . ?
N1 C1 C4 112.43(17) . . ?
N6 C1 N1 119.94(19) . . ?
N6 C1 C4 127.63(19) . . ?
N2 C2 N1 121.75(18) . . ?
N7 C2 N1 116.23(18) . . ?
N7 C2 N2 122.00(18) . . ?
N2 C3 N3 127.89(18) . . ?
N2 C3 C4 127.96(19) . . ?
N3 C3 C4 104.16(17) . . ?
N5 C4 C1 131.51(18) . . ?
N5 C4 C3 109.79(18) . . ?
C3 C4 C1 118.70(18) . . ?
H2A O2 H2B 109(3) . . ?
H3A O3 H3B 95(3) . . ?

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
N6 H6A O2 0.87(3) 1.97(3) 2.830(2) 170(3) . yes
N7 H7B O2 0.87(3) 2.05(3) 2.881(2) 160(3) 4_566 yes
O2 H2B N4 0.81(4) 2.26(4) 3.016(2) 155(3) 1_545 yes
O3 H3A N5 0.84(3) 2.08(3) 2.827(2) 148(2) 4_576 yes
O3 H3B N2 0.92(4) 1.90(4) 2.778(2) 158(4) . yes
O1 H1 O3 0.91(4) 1.59(4) 2.494(2) 171(3) 2_646 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 N6 -1.8(3) . . . . ?
O1 N1 C1 C4 177.39(16) . . . . ?
O1 N1 C2 N2 -174.72(17) . . . . ?
O1 N1 C2 N7 4.3(2) . . . . ?
N1 C1 C4 N5 179.75(19) . . . . ?
N1 C1 C4 C3 -1.0(3) . . . . ?
N2 C3 C4 N5 -179.75(18) . . . . ?
N2 C3 C4 C1 0.8(3) . . . . ?
N3 N4 N5 C4 0.0(2) . . . . ?
N3 C3 C4 N5 0.3(2) . . . . ?
N3 C3 C4 C1 -179.16(17) . . . . ?
N4 N3 C3 N2 179.78(18) . . . . ?
N4 N3 C3 C4 -0.2(2) . . . . ?
N4 N5 C4 C1 179.1(2) . . . . ?
N4 N5 C4 C3 -0.2(2) . . . . ?
N6 C1 C4 N5 -1.1(4) . . . . ?
N6 C1 C4 C3 178.17(19) . . . . ?
C1 N1 C2 N2 3.9(3) . . . . ?
C1 N1 C2 N7 -177.10(18) . . . . ?
C2 N1 C1 N6 179.55(18) . . . . ?
C2 N1 C1 C4 -1.2(3) . . . . ?
C2 N2 C3 N3 -178.43(19) . . . . ?
C2 N2 C3 C4 1.6(3) . . . . ?
C3 N2 C2 N1 -3.8(3) . . . . ?
C3 N2 C2 N7 177.33(18) . . . . ?
C3 N3 N4 N5 0.1(2) . . . . ?

_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 YT-5
_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 1.760
_oxdiff_exptl_absorpt_empirical_full_min 0.710
