# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_aohr-takemura-210908a_auto
_database_code_depnum_ccdc_archive 'CCDC 2091606'
loop_
_audit_author_name
_audit_author_address
'Mitsuru Kondo'
;Shizuoka University
Japan
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2023-02-24 downloaded from the CCDC.
;
_audit_creation_date             2021-09-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C9 H11 N5 O6), 2(H2 O)'
_chemical_formula_sum            'C18 H26 N10 O14'
_chemical_formula_weight         606.49
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H18N10O10
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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   19.32005(12)
_cell_length_b                   5.34244(2)
_cell_length_c                   11.81711(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.3058(4)
_cell_angle_gamma                90
_cell_volume                     1206.924(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    47235
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.6990
_cell_measurement_theta_min      3.7390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.263
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.102a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            53776
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.848
_diffrn_reflns_theta_min         3.780
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_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 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00   7.00   0.50    2.00    --  -46.33 103.00 -38.00  180
  2  ω     -7.00  87.00   0.50    2.00    --   50.08-103.00-140.00  188
  3  ω   -177.00 -84.00   0.50    2.00    -- -104.98-103.00-140.00  186
  4  ω   -107.00 -32.00   0.50    2.00    -- -104.98 103.00 -38.00  150
  5  ω     84.00 178.00   0.50    2.00    --  108.73 103.00 -38.00  188
  6  ω     36.00 106.00   0.50    2.00    --  108.73-103.00-140.00  140
  7  ω   -119.00 -73.00   0.50    2.00    --  -46.33-125.00 -60.00   92
  8  ω   -119.00 -73.00   0.50    2.00    --  -46.33-125.00   0.00   92
  9  ω     34.00 122.00   0.50    2.00    --   50.08  57.00 120.00  176
 10  ω     74.00 122.00   0.50    2.00    --   50.08 125.00-180.00   96
 11  ω     34.00 122.00   0.50    2.00    --   50.08  57.00  30.00  176
 12  ω   -106.00 -32.00   0.50    2.00    -- -104.98  77.00 150.00  148
 13  ω   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00 150.00  176
 14  ω   -112.00 -32.00   0.50    2.00    -- -104.98 125.00 -30.00  160
 15  ω    -67.00 -32.00   0.50    2.00    -- -104.98  57.00 -60.00   70
 16  ω    -67.00 -32.00   0.50    2.00    -- -104.98  57.00-180.00   70
 17  ω    -67.00 -32.00   0.50    2.00    -- -104.98  57.00 120.00   70
 18  ω   -177.00 -90.00   0.50    2.00    -- -104.98 -38.00  60.00  174
 19  ω     36.00  65.00   0.50    2.00    --  108.73 -57.00 -90.00   58
 20  ω     36.00 111.00   0.50    2.00    --  108.73-125.00 150.00  150
 21  ω     36.00  65.00   0.50    2.00    --  108.73 -57.00 120.00   58
 22  ω     36.00  65.00   0.50    2.00    --  108.73 -57.00  90.00   58
 23  ω     93.00 178.00   0.50    2.00    --  108.73  57.00 -60.00  170
 24  ω     36.00 111.00   0.50    2.00    --  108.73-125.00-180.00  150
 25  ω     36.00 111.00   0.50    2.00    --  108.73-125.00   0.00  150
 26  ω     36.00  65.00   0.50    2.00    --  108.73 -57.00-150.00   58
 27  ω     36.00  65.00   0.50    2.00    --  108.73 -57.00   0.00   58
 28  ω     94.00 178.00   0.50    2.00    --  108.73  38.00  60.00  168
 29  ω     36.00 104.00   0.50    2.00    --  108.73 -77.00-150.00  136
 30  ω     36.00  65.00   0.50    2.00    --  108.73 -57.00  30.00   58
 31  ω   -119.00 -23.00   0.50    2.00    --  -46.33 -77.00 -60.00  192
 32  ω     34.00 122.00   0.50    2.00    --   50.08  57.00-120.00  176
 33  ω     27.00 122.00   0.50    2.00    --   50.08  77.00-120.00  190
 34  ω    -25.00  25.00   0.50    2.00    --   50.08 -19.00  90.00  100
 35  ω     27.00 122.00   0.50    2.00    --   50.08  77.00 150.00  190
 36  ω     27.00 122.00   0.50    2.00    --   50.08  77.00  60.00  190
 37  ω     34.00 122.00   0.50    2.00    --   50.08  57.00 -30.00  176
 38  ω   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00  60.00  192
 39  ω   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00 -90.00  176
 40  ω   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00  90.00  192
 41  ω   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00 120.00  176
 42  ω   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00 -90.00  192
 43  ω   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00 -60.00  192
 44  ω   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00 -60.00  176
 45  ω   -177.00 -90.00   0.50    2.00    -- -104.98 -38.00-180.00  174
 46  ω   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00-120.00  192
 47  ω   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00-180.00  192
 48  ω   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00 120.00  192
 49  ω   -177.00 -90.00   0.50    2.00    -- -104.98 -38.00 -60.00  174
 50  ω   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00  30.00  176
 51  ω   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00-150.00  192
 52  ω     36.00 106.00   0.50    2.00    --  108.73 -99.00  30.00  140
 53  ω     93.00 178.00   0.50    2.00    --  108.73  57.00 150.00  170
 54  ω     85.00 178.00   0.50    2.00    --  108.73  77.00 -30.00  186
 55  ω     94.00 178.00   0.50    2.00    --  108.73  38.00-150.00  168
 56  ω     94.00 178.00   0.50    2.00    --  108.73  38.00 -90.00  168
 57  ω     85.00 178.00   0.50    2.00    --  108.73  77.00 -60.00  186
 58  ω     94.00 178.00   0.50    2.00    --  108.73  38.00-120.00  168
 59  ω   -119.00 -23.00   0.50    2.00    --  -46.33 -77.00 -90.00  192
 60  ω   -119.00 -23.00   0.50    2.00    --  -46.33 -77.00-120.00  192
 61  ω     36.00 124.00   0.50    2.00    --   50.08  38.00  60.00  176
 62  ω     36.00 124.00   0.50    2.00    --   50.08  38.00-120.00  176
 63  ω     27.00 122.00   0.50    2.00    --   50.08  77.00  90.00  190
 64  ω     27.00 122.00   0.50    2.00    --   50.08  77.00   0.00  190
 65  ω     27.00 122.00   0.50    2.00    --   50.08  77.00-180.00  190
 66  ω   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00  60.00  176
 67  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00-150.00  290
 68  ω   -177.00 -90.00   0.50    2.00    -- -104.98 -38.00-150.00  174
 69  ω   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00 -30.00  192
 70  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00-180.00  290
 71  ω   -177.00 -90.00   0.50    2.00    -- -104.98 -38.00 120.00  174
 72  ω   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00  90.00  176
 73  ω   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00  30.00  192
 74  ω   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00 150.00  192
 75  ω   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00   0.00  192
 76  ω   -177.00 -90.00   0.50    2.00    -- -104.98 -38.00  90.00  174
 77  ω   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00   0.00  176
 78  ω   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00-180.00  176
 79  ω   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00-150.00  176
 80  ω   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00 -30.00  176
 81  ω     85.00 178.00   0.50    2.00    --  108.73  77.00-150.00  186
 82  ω     85.00 178.00   0.50    2.00    --  108.73  77.00 150.00  186
 83  ω     85.00 178.00   0.50    2.00    --  108.73  77.00  90.00  186
 84  ω     85.00 178.00   0.50    2.00    --  108.73  77.00-120.00  186
 85  ω     93.00 178.00   0.50    2.00    --  108.73  57.00  90.00  170
 86  ω     94.00 178.00   0.50    2.00    --  108.73  38.00 -60.00  168
 87  ω   -119.00 -23.00   0.50    2.00    --  -46.33 -77.00-150.00  192
 88  ω   -119.00 -23.00   0.50    2.00    --  -46.33 -77.00 -30.00  192
 89  ω   -120.00 -32.00   0.50    2.00    --  -46.33 -38.00 -60.00  176
 90  ω   -119.00 -23.00   0.50    2.00    --  -46.33 -77.00  30.00  192
 91  ω     36.00 124.00   0.50    2.00    --   50.08  38.00 150.00  176
 92  ω     34.00 122.00   0.50    2.00    --   50.08  57.00   0.00  176
 93  ω     27.00 122.00   0.50    2.00    --   50.08  77.00-150.00  190
 94  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00  60.00  290
 95  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00   0.00  290
 96  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00   0.00  290
 97  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00  30.00  290
 98  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00  30.00  290
 99  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 120.00  290
100  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00  90.00  290
101  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 -30.00  290
102  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00-120.00  290
103  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 -60.00  290
104  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00-150.00  290
105  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00-180.00  290
106  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 -90.00  290
107  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 -60.00  290
108  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 -30.00  290
109  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 -90.00  290
110  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 150.00  290
111  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00  60.00  290
112  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00  90.00  290
113  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 120.00  290
114  ω   -177.00 -32.00   0.50    2.00    -- -104.98   0.00-120.00  290
115  ω    -23.00  97.00   0.50    2.00    --   50.08   0.00-150.00  240
116  ω    -23.00 123.00   0.50    2.00    --   50.08   0.00-180.00  292
117  ω     47.00  72.00   0.50    2.00    --  108.73-103.00-140.00   50
118  ω     97.00 123.00   0.50    2.00    --   50.33 125.00 -30.00   52
119  ω     80.00 106.00   0.50    2.00    --  108.73 -99.00  90.00   52
120  ω     36.00  61.00   0.50    2.00    --  108.73 -57.00-120.00   50
121  ω     47.00  72.00   0.50    2.00    --  108.73-103.00-140.00   50
122  ω   -119.00  26.00   0.50    2.00    --  -46.58   0.00-180.00  290
123  ω   -120.00 -32.00   0.50    2.00    --  -46.58 -38.00 120.00  176
124  ω   -118.00 -23.00   0.50    2.00    --  -46.58 -77.00 120.00  190
125  ω   -119.00  26.00   0.50    2.00    --  -46.58   0.00 -60.00  290
126  ω   -119.00  26.00   0.50    2.00    --  -46.58   0.00-120.00  290
127  ω   -119.00  26.00   0.50    2.00    --  -46.58   0.00 -90.00  290
128  ω   -119.00  26.00   0.50    2.00    --  -46.58   0.00-150.00  290
129  ω    -23.00 123.00   0.50    2.00    --   50.08   0.00-180.00  292
130  ω     34.00 123.00   0.50    2.00    --   50.33  57.00  60.00  178
131  ω    -22.00 123.00   0.50    2.00    --   50.33   0.00 -60.00  290
132  ω     27.00 123.00   0.50    2.00    --   50.33  77.00 150.00  192
133  ω    -22.00 123.00   0.50    2.00    --   50.33   0.00  30.00  290
134  ω    -22.00 123.00   0.50    2.00    --   50.33   0.00 -30.00  290
135  ω    -22.00  49.50   0.50    2.00    --   50.33   0.00   0.00  143
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0068866000
_diffrn_orient_matrix_UB_12      -0.0018768000
_diffrn_orient_matrix_UB_13      0.1315258000
_diffrn_orient_matrix_UB_21      0.0225155000
_diffrn_orient_matrix_UB_22      0.2768314000
_diffrn_orient_matrix_UB_23      0.0030159000
_diffrn_orient_matrix_UB_31      -0.0770532000
_diffrn_orient_matrix_UB_32      0.0807705000
_diffrn_orient_matrix_UB_33      -0.0072282000
_diffrn_oxdiff_digest_frames     
;
011a030bc60cdd29877739d307a71800eb22022670b
;
_diffrn_oxdiff_digest_hkl        
;
01d21057ccc097e79e3d50be205f5a44dff429
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2514
_reflns_number_total             2516
_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 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1106 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2516
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.064
_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)+(0.0523P)²+0.6405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0784
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O7(H7A,H7B)
2.b Ternary CH refined with riding coordinates:
 C8(H8), C5(H5A), C7(H7), C6(H6A)
2.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.d Aromatic/amide H refined with riding coordinates:
 N5(H5), N1(H1)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O6(H6)
;
_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
O3 O 0.45814(7) 0.8205(3) 0.35406(12) 0.0184(3) Uani 1 1 d . . . . .
H3 H 0.441064 0.961301 0.365550 0.028 Uiso 1 1 calc GR . . . .
O4 O 0.48767(7) 1.0007(3) 0.15367(12) 0.0201(3) Uani 1 1 d . . . . .
H4 H 0.504186 1.103186 0.110735 0.030 Uiso 1 1 calc GR . . . .
O5 O 0.58998(7) 0.4889(3) 0.28407(11) 0.0160(3) Uani 1 1 d . . . . .
O6 O 0.57711(7) 0.3076(3) 0.04249(11) 0.0192(3) Uani 1 1 d . . . . .
H6 H 0.615518 0.232231 0.057106 0.029 Uiso 1 1 calc GR . . . .
O2 O 0.58623(8) 0.2763(3) 0.57127(12) 0.0189(3) Uani 1 1 d . . . . .
O1 O 0.80195(8) 0.5373(3) 0.90014(12) 0.0233(3) Uani 1 1 d . . . . .
O7 O 0.66160(8) -0.0006(3) 0.85440(12) 0.0232(3) Uani 1 1 d . . . . .
H7A H 0.676448 -0.037329 0.925479 0.035 Uiso 1 1 d G . . . .
H7B H 0.616428 -0.018951 0.847587 0.035 Uiso 1 1 d G . . . .
N5 N 0.70902(9) 0.4274(4) 0.75988(13) 0.0168(3) Uani 1 1 d . . . . .
H5 H 0.691287 0.300246 0.793338 0.020 Uiso 1 1 calc R . . . .
N1 N 0.77706(9) 0.7417(3) 0.72475(14) 0.0166(3) Uani 1 1 d . . . . .
H1 H 0.811100 0.852539 0.731866 0.020 Uiso 1 1 calc R . . . .
N4 N 0.62462(8) 0.6119(3) 0.47425(13) 0.0140(3) Uani 1 1 d . . . . .
N3 N 0.66841(9) 0.8045(3) 0.45782(13) 0.0156(3) Uani 1 1 d . . . . .
N2 N 0.71987(9) 0.8569(3) 0.53622(13) 0.0169(3) Uani 1 1 d . . . . .
C2 C 0.72630(10) 0.7158(4) 0.63165(17) 0.0144(4) Uani 1 1 d . . . . .
C3 C 0.68414(10) 0.5209(4) 0.65311(15) 0.0144(4) Uani 1 1 d . . . . .
C8 C 0.54892(10) 0.6014(4) 0.18513(15) 0.0144(4) Uani 1 1 d . . . . .
H8 H 0.501418 0.523145 0.171800 0.017 Uiso 1 1 calc R . . . .
C4 C 0.62774(10) 0.4491(4) 0.56910(16) 0.0141(4) Uani 1 1 d . . . . .
C5 C 0.56523(10) 0.5933(4) 0.38286(16) 0.0136(4) Uani 1 1 d . . . . .
H5A H 0.529433 0.478514 0.407773 0.016 Uiso 1 1 calc R . . . .
C1 C 0.76601(10) 0.5658(4) 0.80514(16) 0.0171(4) Uani 1 1 d . . . . .
C7 C 0.54292(10) 0.8742(4) 0.22155(15) 0.0145(4) Uani 1 1 d . . . . .
H7 H 0.588070 0.963501 0.218210 0.017 Uiso 1 1 calc R . . . .
C9 C 0.58534(10) 0.5613(4) 0.08178(16) 0.0168(4) Uani 1 1 d . . . . .
H9A H 0.565464 0.676306 0.019805 0.020 Uiso 1 1 calc R . . . .
H9B H 0.635736 0.599999 0.101816 0.020 Uiso 1 1 calc R . . . .
C6 C 0.53041(10) 0.8470(4) 0.34698(15) 0.0146(4) Uani 1 1 d . . . . .
H6A H 0.551955 0.987618 0.395707 0.018 Uiso 1 1 calc R . . . .


_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
O3 C6 1.418(2) . ?
O4 C7 1.411(2) . ?
O5 C8 1.445(2) . ?
O5 C5 1.437(2) . ?
O6 C9 1.434(3) . ?
O2 C4 1.226(2) . ?
O1 C1 1.241(2) . ?
N5 C3 1.377(2) . ?
N5 C1 1.369(3) . ?
N1 C2 1.371(2) . ?
N1 C1 1.375(3) . ?
N4 N3 1.364(2) . ?
N4 C4 1.413(2) . ?
N4 C5 1.461(2) . ?
N3 N2 1.288(2) . ?
N2 C2 1.347(3) . ?
C2 C3 1.368(3) . ?
C3 C4 1.417(2) . ?
C8 C7 1.529(3) . ?
C8 C9 1.510(3) . ?
C5 C6 1.545(3) . ?
C7 C6 1.543(2) . ?

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
C5 O5 C8 106.72(13) . . ?
C1 N5 C3 108.45(17) . . ?
C2 N1 C1 108.74(16) . . ?
N3 N4 C4 128.39(15) . . ?
N3 N4 C5 112.52(15) . . ?
C4 N4 C5 118.92(16) . . ?
N2 N3 N4 119.47(16) . . ?
N3 N2 C2 116.66(17) . . ?
N2 C2 N1 125.75(18) . . ?
N2 C2 C3 126.56(18) . . ?
C3 C2 N1 107.69(17) . . ?
N5 C3 C4 132.44(19) . . ?
C2 C3 N5 107.91(17) . . ?
C2 C3 C4 119.63(17) . . ?
O5 C8 C7 102.93(14) . . ?
O5 C8 C9 109.26(15) . . ?
C9 C8 C7 115.21(16) . . ?
O2 C4 N4 121.81(17) . . ?
O2 C4 C3 128.95(18) . . ?
N4 C4 C3 109.24(17) . . ?
O5 C5 N4 108.00(14) . . ?
O5 C5 C6 107.49(14) . . ?
N4 C5 C6 114.06(16) . . ?
O1 C1 N5 126.9(2) . . ?
O1 C1 N1 125.92(19) . . ?
N5 C1 N1 107.19(16) . . ?
O4 C7 C8 112.24(15) . . ?
O4 C7 C6 112.37(15) . . ?
C8 C7 C6 102.08(14) . . ?
O6 C9 C8 110.67(16) . . ?
O3 C6 C5 106.85(15) . . ?
O3 C6 C7 111.00(14) . . ?
C7 C6 C5 102.94(14) . . ?

_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 1.935
_oxdiff_exptl_absorpt_empirical_full_min 0.322
