# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_js1020a
_database_code_depnum_ccdc_archive 'CCDC 2036394'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2020-10-09 deposited with the CCDC.	2020-11-25 downloaded from the CCDC.
;
_audit_creation_date             2020-10-06
_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         'C3 N5 O6, H2 O, C3 H6 N7'
_chemical_formula_sum            'C6 H8 N12 O7'
_chemical_formula_weight         360.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         C8H11H21O2
_chemical_oxdiff_usercomment     TTT-3
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                   13.6133(4)
_cell_length_b                   4.83877(10)
_cell_length_c                   20.4591(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.220(3)
_cell_angle_gamma                90
_cell_volume                     1333.83(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3775
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.3180
_cell_measurement_theta_min      3.6920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.424
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.482
_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    1.794
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0080
-1 0 0 0.0080
1 -1 -1 0.1326
-1 1 1 0.1554
0 0 1 0.0315
0 0 -1 0.0178

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.016
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
1.0007 -0.0003 -0.0009 0.0801 0.0303 0.0758
-1.0007 0.0003 0.0009 -0.0801 -0.0303 -0.0758
1.0014 -1.0006 -0.9982 0.0328 -0.2572 0.2250
-1.0014 1.0006 0.9982 -0.0328 0.2572 -0.2250
0.0006 0.0008 0.9995 -0.0417 0.0485 0.0411
-0.0006 -0.0008 -0.9995 0.0417 -0.0485 -0.0411

_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  0.1288
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29865
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.645
_diffrn_reflns_theta_min         3.671
_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 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  19.00   0.50    0.05    --    6.00  52.00  -3.51   52
  2  ω    -11.00  15.00   0.50    0.05    --    2.00  57.00 -38.76   52
  3  ω     -8.00  17.00   0.50    0.05    --    6.00  54.00 -94.35   50
  4  ω     30.00  72.00   0.50    0.05    --   47.57  65.00 -91.00   84
  5  ω    -13.00  14.00   0.50    0.05    --    2.00  58.00 169.92   54
  6  ω    -77.00 -34.00   0.50    0.05    --  -47.57 125.00 -60.00   86
  7  ω    -63.00 -15.00   0.50    0.05    --  -47.57  65.00 -91.00   96
  8  ω     -8.00  18.00   0.50    0.05    --  -47.57  65.00 -91.00   52
  9  ω    -44.00 -18.00   0.50    0.20    --  -86.25  65.00 -91.00   52
 10  ω    -75.00 -49.00   0.50    0.20    --  -86.25  65.00 -91.00   52
 11  ω   -159.00-134.00   0.50    0.20    --  -86.25 -77.00  60.00   50
 12  ω   -156.00-130.00   0.50    0.20    --  -86.25 -65.00 132.00   52
 13  ω   -112.00 -68.00   0.50    0.20    --  -86.25 -65.00 132.00   88
 14  ω    -97.00 -45.00   0.50    0.05    --  -58.00 -30.00 131.84  104
 15  ω    -93.00 -48.00   0.50    0.05    --  -58.00 -30.00 -30.80   90
 16  ω    -91.00 -65.00   0.50    0.20    --  -78.00 -30.00  31.49   52
 17  ω   -131.00-102.00   0.50    0.05    --  -58.00 -30.00 -30.80   58
 18  ω   -104.00 -75.00   0.50    0.05    --  -54.00 -30.00 -89.70   58
 19  ω    -92.00 -45.00   0.50    0.05    --  -58.00 -30.00-124.82   94
 20  ω   -133.00 -95.00   0.50    0.05    --  -58.00 -30.00-124.82   76
 21  ω   -151.00-125.00   0.50    0.20    --  -78.00 -30.00-125.74   52
 22  ω    -95.00 -65.00   0.50    0.20    --  -78.00 -30.00-125.74   60
 23  ω    -94.00 -69.00   0.50    0.20    --  -82.00 -30.00 -71.81   50
 24  ω    -94.00 -69.00   0.50    0.20    --  -82.00 -30.00 -41.61   50
 25  ω    -94.00 -69.00   0.50    0.20    --  -82.00 -30.00 -24.18   50
 26  ω    -99.00 -69.00   0.50    0.20    --  -82.00 -30.00-151.34   60
 27  ω    -96.00 -69.00   0.50    0.20    --  -82.00 -30.00   3.59   54
 28  ω    -94.00 -69.00   0.50    0.20    --  -82.00 -30.00  63.69   50
 29  ω   -114.00 -72.00   0.50    0.20    --  -82.00 -30.00 118.81   84
 30  ω    -99.00 -69.00   0.50    0.20    --  -82.00 -30.00 133.61   60
 31  ω   -155.00-130.00   0.50    0.20    --  -82.00 -30.00 118.81   50
 32  ω   -146.00-120.00   0.50    0.20    --  -82.00 -30.00  63.69   52
 33  ω   -156.00-130.00   0.50    0.20    --  -82.00 -30.00   3.59   52
 34  ω   -100.00 -74.00   0.50    0.20    --  -86.25 -29.00 -48.55   52
 35  ω    -96.00 -70.00   0.50    0.20    --  -82.00 -30.00 -85.62   52
 36  ω    -66.00 -41.00   0.50    0.05    --  -54.00 -30.00 -89.70   50
 37  ω   -101.00 -74.00   0.50    0.20    --  -86.25 -29.00-169.54   54
 38  ω   -148.00-122.00   0.50    0.20    --  -86.25 -29.00-169.54   52
 39  ω    -99.00 -74.00   0.50    0.20    --  -86.25 -29.00 -99.30   50
 40  ω   -157.00-123.00   0.50    0.20    --  -86.25 -29.00 -48.55   68
 41  ω   -159.00-129.00   0.50    0.20    --  -86.25 -29.00  47.99   60
 42  ω   -103.00 -74.00   0.50    0.20    --  -86.25 -29.00  22.92   58
 43  ω    -99.00 -74.00   0.50    0.20    --  -86.25 -29.00  47.99   50
 44  ω   -161.00-126.00   0.50    0.20    --  -86.25 -29.00 174.45   70
 45  ω    -99.00 -74.00   0.50    0.20    --  -86.25 -29.00 155.41   50
 46  ω   -100.00 -74.00   0.50    0.20    --  -86.25 -29.00 174.45   52
 47  ω   -118.00 -30.00   0.50    0.05    --  -47.57 -65.00 132.00  176
 48  ω    -53.00 -28.00   0.50    0.05    --  -42.00 -33.00 133.84   50
 49  ω    -53.00 -28.00   0.50    0.05    --  -42.00 -33.00 122.97   50
 50  ω    -58.00 -29.00   0.50    0.05    --  -42.00 -32.00  30.78   58
 51  ω    -47.00 -22.00   0.50    0.05    --  -34.00 -35.00  -1.15   50
 52  ω    -30.00  -5.00   0.50    0.05    --  -18.00 -44.00 -60.42   50
 53  ω    -46.00 -21.00   0.50    0.05    --  -34.00 -35.00 -90.70   50
 54  ω    -54.00 -29.00   0.50    0.05    --  -42.00 -33.00-123.14   50
 55  ω    -61.00 -36.00   0.50    0.05    --  -47.57 -31.00-175.67   50
 56  ω    -58.00 -32.00   0.50    0.05    --  -42.00 -32.00 -13.40   52
 57  ω    -64.00 -39.00   0.50    0.05    --  -47.57 -31.00 164.99   50
 58  ω   -156.00-107.00   0.50    0.20    --  -86.25-125.00 -90.00   98
 59  ω    -23.00  47.00   0.50    0.05    --   47.57 -65.00 132.00  140
 60  ω     35.00  77.00   0.50    0.20    --  107.11 -65.00 132.00   84
 61  ω     36.00  63.00   0.50    0.20    --  107.11 -57.00  30.00   54
 62  ω     35.00  65.00   0.50    0.20    --  107.11 -57.00 -30.00   60
 63  ω     36.00  62.00   0.50    0.20    --  107.11 -57.00-150.00   52
 64  ω     36.00  70.00   0.50    0.20    --  107.11 -99.00-120.00   68
 65  ω     38.00  64.00   0.50    0.20    --  107.11 -99.00 -90.00   52
 66  ω     37.00 103.00   0.50    0.20    --  107.11-125.00-120.00  132
 67  ω     65.00 104.00   0.50    0.20    --  107.11 -99.00 -90.00   78
 68  ω     37.00 101.00   0.50    0.20    --  107.11-125.00 -30.00  128
 69  ω     35.00 103.00   0.50    0.20    --  107.11 -99.00 -30.00  136
 70  ω     35.00 103.00   0.50    0.20    --  107.11 -99.00   0.00  136
 71  ω     67.00 104.00   0.50    0.20    --  107.11 -99.00  60.00   74
 72  ω     35.00 104.00   0.50    0.20    --  107.11 -99.00 150.00  138
 73  ω     37.00 104.00   0.50    0.20    --  107.11 -99.00 120.00  134
 74  ω     39.00  91.00   0.50    0.20    --  107.11 -99.00  90.00  104
 75  ω     36.00  61.00   0.50    0.20    --  107.11 -99.00  60.00   50
 76  ω     78.00 103.00   0.50    0.20    --  107.11 -99.00-120.00   50
 77  ω     95.00 156.00   0.50    0.20    --  107.11  19.00  90.00  122
 78  ω    152.00 178.00   0.50    0.20    --  107.11  57.00 -30.00   52
 79  ω    118.00 173.00   0.50    0.20    --  107.11  37.00 -60.00  110
 80  ω    114.00 177.00   0.50    0.20    --  107.11  37.00 -90.00  126
 81  ω    136.00 166.00   0.50    0.20    --  107.11  65.00 -91.00   60
 82  ω     89.00 122.00   0.50    0.20    --  107.11  65.00 -91.00   66
 83  ω    114.00 175.00   0.50    0.20    --  107.11  37.00 -30.00  122
 84  ω     95.00 178.00   0.50    0.20    --  107.11  28.00-113.33  166
 85  ω     94.00 178.00   0.50    0.20    --  107.11  28.00-175.95  168
 86  ω     95.00 171.00   0.50    0.20    --  107.11  26.00  11.71  152
 87  ω    138.00 163.00   0.50    0.20    --  107.11  19.00  60.00   50
 88  ω    138.00 178.00   0.50    0.20    --  107.11  28.00 110.57   80
 89  ω     94.00 135.00   0.50    0.20    --  107.11  28.00 110.57   82
 90  ω     96.00 178.00   0.50    0.20    --  107.11  29.00 137.74  164
 91  ω     95.00 127.00   0.50    0.20    --  107.11  19.00  60.00   64
 92  ω     95.00 151.00   0.50    0.20    --  107.11  19.00-120.00  112
;
_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      0.0800378000
_diffrn_orient_matrix_UB_12      0.0891154000
_diffrn_orient_matrix_UB_13      -0.0418478000
_diffrn_orient_matrix_UB_21      0.0303897000
_diffrn_orient_matrix_UB_22      0.2392644000
_diffrn_orient_matrix_UB_23      0.0483558000
_diffrn_orient_matrix_UB_31      0.0757561000
_diffrn_orient_matrix_UB_32      -0.1902175000
_diffrn_orient_matrix_UB_33      0.0412419000
_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                2020
_reflns_number_total             2788
_reflns_odcompleteness_completeness 99.81
_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    
;
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         0.338
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2788
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.129
_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)+(0.0459P)²+1.0983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1345
_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 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 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 0.66906(15) -0.0147(4) 0.67218(10) 0.0306(5) Uani 1 1 d . . . . .
O2 O 0.81347(15) -0.1207(4) 0.72684(10) 0.0307(5) Uani 1 1 d . . . . .
O3 O 1.02463(16) -0.0771(4) 0.68226(10) 0.0319(5) Uani 1 1 d . . . A 1
O4 O 1.01879(15) 0.2810(4) 0.74472(9) 0.0297(5) Uani 1 1 d . . . B 1
O5 O 1.07555(14) 0.4726(4) 0.60347(9) 0.0259(4) Uani 1 1 d . . . . .
O6 O 0.98462(15) 0.7617(4) 0.53968(9) 0.0269(4) Uani 1 1 d . . . . .
N8 N 0.75327(17) 0.3780(5) 0.60424(11) 0.0234(5) Uani 1 1 d . . . . .
N9 N 0.81693(17) 0.5343(4) 0.57536(11) 0.0232(5) Uani 1 1 d . . . . .
N10 N 0.75918(17) 0.0133(4) 0.68509(11) 0.0244(5) Uani 1 1 d . . . . .
N11 N 0.98971(16) 0.1442(4) 0.69542(11) 0.0218(5) Uani 1 1 d . . . . .
N12 N 0.99513(17) 0.5725(4) 0.58034(11) 0.0218(5) Uani 1 1 d . . . . .
C4 C 0.8073(2) 0.2126(5) 0.64840(12) 0.0213(5) Uani 1 1 d . . . . .
C5 C 0.90740(19) 0.2576(5) 0.65032(12) 0.0202(5) Uani 1 1 d . . . . .
C6 C 0.90864(19) 0.4600(5) 0.60271(12) 0.0203(5) Uani 1 1 d . . . . .
O1W O 1.26522(16) 0.2941(4) 0.71334(10) 0.0320(5) Uani 1 1 d G . . . .
H1WA H 1.263786 0.426288 0.740519 0.048 Uiso 1 1 d G U . . .
H1WB H 1.240828 0.347983 0.674871 0.048 Uiso 1 1 d G U . . .
N1 N 0.63284(17) 0.0601(5) 0.47362(11) 0.0221(5) Uani 1 1 d . . . . .
H1 H 0.623(3) -0.059(8) 0.5028(19) 0.046(11) Uiso 1 1 d . . . . .
N2 N 0.70309(17) 0.3454(5) 0.40479(11) 0.0241(5) Uani 1 1 d . . . . .
N3 N 0.60206(16) 0.3975(4) 0.40448(10) 0.0208(5) Uani 1 1 d . . . . .
N4 N 0.44933(17) 0.4988(5) 0.40028(11) 0.0227(5) Uani 1 1 d . . . . .
H4 H 0.382(2) 0.574(7) 0.3925(15) 0.030(8) Uiso 1 1 d . . . . .
N5 N 0.46543(17) 0.2795(4) 0.44535(11) 0.0226(5) Uani 1 1 d . . . . .
N6 N 0.80293(19) 0.0093(5) 0.46556(13) 0.0285(5) Uani 1 1 d . . . . .
H6A H 0.854(3) 0.071(8) 0.4533(19) 0.044(11) Uiso 1 1 d . . . . .
H6B H 0.805(3) -0.124(8) 0.4919(18) 0.041(10) Uiso 1 1 d . . . . .
N7 N 0.54372(19) 0.7723(4) 0.33285(11) 0.0231(5) Uani 1 1 d . . . . .
H7A H 0.602(3) 0.755(7) 0.3121(17) 0.035(9) Uiso 1 1 d . . . . .
H7B H 0.482(3) 0.840(8) 0.3121(18) 0.045(10) Uiso 1 1 d . . . . .
C1 C 0.7173(2) 0.1394(5) 0.44788(13) 0.0229(6) Uani 1 1 d . . . . .
C2 C 0.5305(2) 0.5691(5) 0.37508(12) 0.0213(5) Uani 1 1 d . . . . .
C3 C 0.55929(19) 0.2304(5) 0.44551(12) 0.0207(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 N10 1.225(3) . ?
O2 N10 1.231(3) . ?
O3 N11 1.217(3) . ?
O4 N11 1.224(3) . ?
O5 N12 1.228(3) . ?
O6 N12 1.231(3) . ?
N8 N9 1.349(3) . ?
N8 C4 1.344(3) . ?
N9 C6 1.342(3) . ?
N10 C4 1.436(3) . ?
N11 C5 1.453(3) . ?
N12 C6 1.431(3) . ?
C4 C5 1.376(4) . ?
C5 C6 1.383(4) . ?
O1W H1WA 0.8495 . ?
O1W H1WB 0.8503 . ?
N1 H1 0.86(4) . ?
N1 C1 1.386(3) . ?
N1 C3 1.359(3) . ?
N2 N3 1.397(3) . ?
N2 C1 1.327(3) . ?
N3 C2 1.354(3) . ?
N3 C3 1.356(3) . ?
N4 H4 0.98(3) . ?
N4 N5 1.403(3) . ?
N4 C2 1.328(3) . ?
N5 C3 1.299(3) . ?
N6 H6A 0.82(4) . ?
N6 H6B 0.84(4) . ?
N6 C1 1.328(4) . ?
N7 H7A 0.95(3) . ?
N7 H7B 0.94(4) . ?
N7 C2 1.338(3) . ?

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
C4 N8 N9 107.7(2) . . ?
C6 N9 N8 106.5(2) . . ?
O1 N10 O2 125.1(2) . . ?
O1 N10 C4 118.6(2) . . ?
O2 N10 C4 116.3(2) . . ?
O3 N11 O4 124.6(2) . . ?
O3 N11 C5 118.8(2) . . ?
O4 N11 C5 116.6(2) . . ?
O5 N12 O6 124.4(2) . . ?
O5 N12 C6 117.1(2) . . ?
O6 N12 C6 118.5(2) . . ?
N8 C4 N10 120.3(2) . . ?
N8 C4 C5 111.7(2) . . ?
C5 C4 N10 128.0(2) . . ?
C4 C5 N11 129.0(2) . . ?
C4 C5 C6 101.8(2) . . ?
C6 C5 N11 128.9(2) . . ?
N9 C6 N12 121.6(2) . . ?
N9 C6 C5 112.3(2) . . ?
C5 C6 N12 126.0(2) . . ?
H1WA O1W H1WB 109.4 . . ?
C1 N1 H1 132(3) . . ?
C3 N1 H1 122(3) . . ?
C3 N1 C1 105.8(2) . . ?
C1 N2 N3 100.9(2) . . ?
C2 N3 N2 139.3(2) . . ?
C2 N3 C3 107.2(2) . . ?
C3 N3 N2 113.5(2) . . ?
N5 N4 H4 116.3(19) . . ?
C2 N4 H4 130.9(19) . . ?
C2 N4 N5 112.9(2) . . ?
C3 N5 N4 101.6(2) . . ?
H6A N6 H6B 122(4) . . ?
C1 N6 H6A 119(3) . . ?
C1 N6 H6B 119(2) . . ?
H7A N7 H7B 125(3) . . ?
C2 N7 H7A 115(2) . . ?
C2 N7 H7B 111(2) . . ?
N2 C1 N1 114.2(2) . . ?
N2 C1 N6 125.2(3) . . ?
N6 C1 N1 120.6(2) . . ?
N4 C2 N3 104.9(2) . . ?
N4 C2 N7 129.4(2) . . ?
N7 C2 N3 125.6(2) . . ?
N3 C3 N1 105.5(2) . . ?
N5 C3 N1 140.9(2) . . ?
N5 C3 N3 113.5(2) . . ?

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
O1W H1WA O1W 0.85 2.08 2.907(2) 164.9 2_756 yes
O1W H1WB N2 0.85 2.41 3.061(3) 134.1 3_766 yes
N1 H1 N5 0.86(4) 2.02(4) 2.806(3) 153(4) 3_656 yes
N4 H4 N8 0.98(3) 1.87(3) 2.810(3) 161(3) 3_666 yes
N6 H6B O6 0.84(4) 2.57(4) 2.963(3) 110(3) 1_545 yes
N7 H7A O1W 0.95(3) 1.97(4) 2.909(3) 169(3) 3_766 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 N10 C4 N8 4.7(4) . . . . ?
O1 N10 C4 C5 -173.0(2) . . . . ?
O2 N10 C4 N8 -176.6(2) . . . . ?
O2 N10 C4 C5 5.7(4) . . . . ?
O3 N11 C5 C4 87.3(3) . . . . ?
O3 N11 C5 C6 -100.2(3) . . . . ?
O4 N11 C5 C4 -92.4(3) . . . . ?
O4 N11 C5 C6 80.1(3) . . . . ?
O5 N12 C6 N9 -172.8(2) . . . . ?
O5 N12 C6 C5 3.2(4) . . . . ?
O6 N12 C6 N9 7.3(3) . . . . ?
O6 N12 C6 C5 -176.6(2) . . . . ?
N8 N9 C6 N12 175.8(2) . . . . ?
N8 N9 C6 C5 -0.7(3) . . . . ?
N8 C4 C5 N11 173.0(2) . . . . ?
N8 C4 C5 C6 -1.1(3) . . . . ?
N9 N8 C4 N10 -177.4(2) . . . . ?
N9 N8 C4 C5 0.7(3) . . . . ?
N10 C4 C5 N11 -9.1(4) . . . . ?
N10 C4 C5 C6 176.8(2) . . . . ?
N11 C5 C6 N9 -173.0(2) . . . . ?
N11 C5 C6 N12 10.7(4) . . . . ?
C4 N8 N9 C6 0.0(3) . . . . ?
C4 C5 C6 N9 1.1(3) . . . . ?
C4 C5 C6 N12 -175.2(2) . . . . ?
N2 N3 C2 N4 -179.2(3) . . . . ?
N2 N3 C2 N7 -2.5(5) . . . . ?
N2 N3 C3 N1 -0.6(3) . . . . ?
N2 N3 C3 N5 179.8(2) . . . . ?
N3 N2 C1 N1 0.4(3) . . . . ?
N3 N2 C1 N6 179.1(3) . . . . ?
N4 N5 C3 N1 -179.8(3) . . . . ?
N4 N5 C3 N3 -0.4(3) . . . . ?
N5 N4 C2 N3 -1.0(3) . . . . ?
N5 N4 C2 N7 -177.5(2) . . . . ?
C1 N1 C3 N3 0.8(3) . . . . ?
C1 N1 C3 N5 -179.8(3) . . . . ?
C1 N2 N3 C2 -180.0(3) . . . . ?
C1 N2 N3 C3 0.1(3) . . . . ?
C2 N3 C3 N1 179.5(2) . . . . ?
C2 N3 C3 N5 -0.1(3) . . . . ?
C2 N4 N5 C3 0.9(3) . . . . ?
C3 N1 C1 N2 -0.8(3) . . . . ?
C3 N1 C1 N6 -179.5(2) . . . . ?
C3 N3 C2 N4 0.7(3) . . . . ?
C3 N3 C2 N7 177.4(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 YT4
_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 1.836
_oxdiff_exptl_absorpt_empirical_full_min 0.617
####################################################################### 
# 
# 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_js1020f
_database_code_depnum_ccdc_archive 'CCDC 2036395'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2020-10-09 deposited with the CCDC.	2020-11-25 downloaded from the CCDC.
;
_audit_creation_date             2020-10-08
_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         'C3 H5 N7'
_chemical_formula_sum            'C3 H5 N7'
_chemical_formula_weight         139.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         C3H5N7
_chemical_oxdiff_usercomment     YT1
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'

_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                   10.5503(4)
_cell_length_b                   3.56337(11)
_cell_length_c                   14.3130(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.468(4)
_cell_angle_gamma                90
_cell_volume                     523.29(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3273
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      76.3800
_cell_measurement_theta_min      4.6650
_shelx_estimated_absorpt_T_max   0.893
_shelx_estimated_absorpt_T_min   0.863
_exptl_absorpt_coefficient_mu    1.134
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.742
_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    1.766
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             288
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0652
0 1 0 0.0652
0 0 1 0.0411
0 0 -1 0.0611
1 0 1 0.0455
-1 0 -1 0.0615
-7 0 5 0.0603
7 0 -5 0.0603
-2 0 5 0.0419

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.102
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 -1.0000 0.0000 -0.2244 0.3482 0.1237
0.0000 1.0000 -0.0000 0.2244 -0.3482 -0.1237
-0.0000 0.0000 1.0000 -0.0266 -0.0508 0.0947
0.0000 -0.0000 -1.0000 0.0266 0.0508 -0.0947
1.0000 0.0000 1.0000 -0.1548 -0.1216 0.0615
-1.0000 -0.0000 -1.0000 0.1548 0.1216 -0.0615
-6.5637 0.0429 4.6434 0.7275 0.2144 0.6517
6.5637 -0.0429 -4.6434 -0.7275 -0.2144 -0.6517
-2.0000 0.0000 5.0000 0.1233 -0.1121 0.5396

_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  0.0360
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4889
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.646
_diffrn_reflns_theta_min         4.721
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    119.00 177.00   0.50    0.05    --  107.11  37.00 150.00  116
  2  ω    150.00 177.00   0.50    0.05    --  107.11  37.00  90.00   54
  3  ω    118.00 144.00   0.50    0.05    --  107.11  37.00  90.00   52
  4  ω    127.00 177.00   0.50    0.05    --  107.11  77.00  30.00  100
  5  ω    134.00 160.00   0.50    0.05    --  107.11  57.00-180.00   52
  6  ω    -27.00   5.00   0.50    0.05    --  -47.45  19.00 120.00   64
  7  ω    -22.00  15.00   0.50    0.05    --  -47.45  19.00 -30.00   74
  8  ω    -61.00 -29.00   0.50    0.05    --  -47.45  57.00-120.00   64
  9  ω    -21.00  15.00   0.50    0.05    --  -47.45  57.00-120.00   72
 10  ω    -43.00 -18.00   0.50    0.05    --  -86.25  37.00 -30.00   50
 11  ω    -69.00 -30.00   0.50    0.05    --  -47.45 125.00   0.00   78
 12  ω    -17.00  12.00   0.50    0.05    --  -47.45 102.00  -5.00   58
 13  ω    -73.00 -22.00   0.50    0.05    --  -47.45 102.00  -5.00  102
 14  ω    -77.00 -40.00   0.50    0.05    --  -86.25 102.00  -5.00   74
 15  ω    -43.00 -17.00   0.50    0.05    --  -86.25  37.00  30.00   52
 16  ω   -151.00-116.00   0.50    0.05    --  -86.25 -37.00 150.00   70
 17  ω   -159.00-116.00   0.50    0.05    --  -86.25 -37.00 120.00   86
 18  ω   -157.00-131.00   0.50    0.05    --  -86.25 -37.00  90.00   52
 19  ω   -157.00-128.00   0.50    0.05    --  -86.25 -77.00   0.00   58
 20  ω   -158.00-114.00   0.50    0.05    --  -86.25 -37.00   0.00   88
 21  ω   -159.00-120.00   0.50    0.05    --  -86.25 -37.00 -90.00   78
 22  ω   -159.00-134.00   0.50    0.05    --  -86.25 -57.00 -90.00   50
 23  ω   -124.00 -99.00   0.50    0.05    --  -86.25-102.00-108.00   50
 24  ω     37.00  65.00   0.50    0.05    --  107.11 -57.00 150.00   56
 25  ω     42.00  86.00   0.50    0.05    --  107.11 -77.00  90.00   88
 26  ω     38.00  63.00   0.50    0.05    --  107.11 -57.00  90.00   50
 27  ω     35.00  60.00   0.50    0.05    --  107.11 -57.00  30.00   50
 28  ω    109.00 162.00   0.50    0.05    --  107.11 102.00  -5.00  106
 29  ω     39.00  65.00   0.50    0.05    --  107.11 -57.00 -30.00   52
 30  ω     39.00  64.00   0.50    0.05    --  107.11 -57.00 -60.00   50
 31  ω     -4.00  22.00   0.50    0.05    --   47.45 -19.00-120.00   52
 32  ω     39.00  64.00   0.50    0.05    --  107.11 -99.00 -30.00   50
 33  ω     77.00 108.00   0.50    0.05    --  107.11-125.00  90.00   62
 34  ω     38.00  69.00   0.50    0.05    --  107.11-125.00  90.00   62
 35  ω     24.00  51.00   0.50    0.05    --   47.45-102.00-108.00   54
 36  ω     75.00 102.00   0.50    0.05    --  107.11-125.00-150.00   54
 37  ω     75.00 108.00   0.50    0.05    --  107.11-125.00-180.00   66
 38  ω     49.00  74.00   0.50    0.05    --  107.11-125.00-180.00   50
 39  ω     41.00  66.00   0.50    0.05    --  107.11-125.00-150.00   50
 40  ω     61.00 100.00   0.50    0.05    --  107.11-102.00-108.00   78
 41  ω     79.00 104.00   0.50    0.05    --  107.11 -99.00 -30.00   50
 42  ω     36.00 100.00   0.50    0.05    --  107.11 -99.00 -60.00  128
;
_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      -0.1281967000
_diffrn_orient_matrix_UB_12      0.2244061000
_diffrn_orient_matrix_UB_13      -0.0266138000
_diffrn_orient_matrix_UB_21      -0.0708549000
_diffrn_orient_matrix_UB_22      -0.3482088000
_diffrn_orient_matrix_UB_23      -0.0507580000
_diffrn_orient_matrix_UB_31      -0.0331330000
_diffrn_orient_matrix_UB_32      -0.1236954000
_diffrn_orient_matrix_UB_33      0.0946644000
_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                1009
_reflns_number_total             1079
_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         0.233
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0191(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1079
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.092
_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)+(0.0439P)²+0.2307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0876
_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
N1 N 0.42276(11) 0.7427(3) 0.58840(8) 0.0158(3) Uani 1 1 d . . . . .
N2 N 0.35888(10) 0.8884(3) 0.65630(8) 0.0152(3) Uani 1 1 d . . . . .
N3 N 0.21819(10) 0.7619(3) 0.52107(7) 0.0131(3) Uani 1 1 d . . . . .
N4 N 0.12087(10) 0.6851(3) 0.43962(7) 0.0140(3) Uani 1 1 d . . . . .
N5 N 0.32532(10) 0.5202(3) 0.41931(7) 0.0143(3) Uani 1 1 d . . . . .
N6 N 0.13306(10) 0.9974(3) 0.65058(8) 0.0164(3) Uani 1 1 d . . . . .
N7 N 0.13893(11) 0.4508(3) 0.28860(8) 0.0162(3) Uani 1 1 d . . . . .
C1 C 0.33532(12) 0.6628(4) 0.50742(9) 0.0137(3) Uani 1 1 d . . . . .
C2 C 0.23364(12) 0.8962(4) 0.61275(9) 0.0135(3) Uani 1 1 d . . . . .
C3 C 0.19277(12) 0.5438(3) 0.38256(9) 0.0132(3) Uani 1 1 d . . . . .
H7A H 0.1825(17) 0.263(5) 0.2652(13) 0.026(4) Uiso 1 1 d . . . . .
H6A H 0.1503(16) 1.109(5) 0.7085(13) 0.022(4) Uiso 1 1 d . . . . .
H1 H 0.5069(19) 0.692(6) 0.6033(13) 0.035(5) Uiso 1 1 d . . . . .
H7B H 0.0497(18) 0.424(5) 0.2751(12) 0.023(4) Uiso 1 1 d . . . . .
H6B H 0.0584(19) 1.076(6) 0.6092(13) 0.031(5) 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
N1 N2 1.4047(14) . ?
N1 C1 1.3332(17) . ?
N1 H1 0.88(2) . ?
N2 C2 1.3234(16) . ?
N3 N4 1.3896(14) . ?
N3 C1 1.3426(16) . ?
N3 C2 1.3703(16) . ?
N4 C3 1.3357(16) . ?
N5 C1 1.3407(16) . ?
N5 C3 1.3772(16) . ?
N6 C2 1.3480(16) . ?
N6 H6A 0.900(18) . ?
N6 H6B 0.91(2) . ?
N7 C3 1.3731(16) . ?
N7 H7A 0.917(19) . ?
N7 H7B 0.921(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
N2 N1 H1 121.8(12) . . ?
C1 N1 N2 109.51(10) . . ?
C1 N1 H1 128.3(12) . . ?
C2 N2 N1 105.62(10) . . ?
C1 N3 N4 110.57(10) . . ?
C1 N3 C2 108.84(11) . . ?
C2 N3 N4 140.55(10) . . ?
C3 N4 N3 99.98(9) . . ?
C1 N5 C3 100.76(10) . . ?
C2 N6 H6A 118.7(11) . . ?
C2 N6 H6B 117.5(12) . . ?
H6A N6 H6B 115.0(16) . . ?
C3 N7 H7A 113.9(11) . . ?
C3 N7 H7B 113.6(10) . . ?
H7A N7 H7B 115.0(16) . . ?
N1 C1 N3 106.94(11) . . ?
N1 C1 N5 141.78(12) . . ?
N5 C1 N3 111.29(11) . . ?
N2 C2 N3 109.07(11) . . ?
N2 C2 N6 127.55(11) . . ?
N6 C2 N3 123.29(11) . . ?
N4 C3 N5 117.40(11) . . ?
N4 C3 N7 121.70(11) . . ?
N7 C3 N5 120.73(11) . . ?

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 N2 0.900(18) 2.198(18) 3.0788(16) 166.2(15) 2_556 yes
N1 H1 N5 0.88(2) 2.02(2) 2.8444(15) 155.3(17) 3_666 yes
N6 H6B N4 0.91(2) 2.04(2) 2.9177(15) 160.1(17) 3_576 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
N1 N2 C2 N3 -0.08(13) . . . . ?
N1 N2 C2 N6 176.55(12) . . . . ?
N2 N1 C1 N3 1.46(14) . . . . ?
N2 N1 C1 N5 -178.44(16) . . . . ?
N3 N4 C3 N5 0.45(14) . . . . ?
N3 N4 C3 N7 -174.85(11) . . . . ?
N4 N3 C1 N1 -179.62(10) . . . . ?
N4 N3 C1 N5 0.32(15) . . . . ?
N4 N3 C2 N2 178.21(14) . . . . ?
N4 N3 C2 N6 1.4(2) . . . . ?
C1 N1 N2 C2 -0.86(14) . . . . ?
C1 N3 N4 C3 -0.44(13) . . . . ?
C1 N3 C2 N2 0.99(14) . . . . ?
C1 N3 C2 N6 -175.82(12) . . . . ?
C1 N5 C3 N4 -0.28(14) . . . . ?
C1 N5 C3 N7 175.07(12) . . . . ?
C2 N3 N4 C3 -177.63(15) . . . . ?
C2 N3 C1 N1 -1.50(14) . . . . ?
C2 N3 C1 N5 178.44(10) . . . . ?
C3 N5 C1 N1 179.87(17) . . . . ?
C3 N5 C1 N3 -0.04(13) . . . . ?

_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 YT1
_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 1.310
_oxdiff_exptl_absorpt_empirical_full_min 0.802
