# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_22019568_0m
_database_code_depnum_ccdc_archive 'CCDC 1918909'
loop_
_audit_author_name
_audit_author_address
'hualin xiong'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-05-27 deposited with the CCDC.	2022-09-20 downloaded from the CCDC.
;
_audit_creation_date             2019-05-20
_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         'C5 H N9 O4'
_chemical_formula_sum            'C5 H N9 O4'
_chemical_formula_weight         251.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.324(3)
_cell_length_b                   11.795(4)
_cell_length_c                   9.195(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.308(9)
_cell_angle_gamma                90
_cell_volume                     914.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2204
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.756
_cell_measurement_theta_min      2.416
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1363 before and 0.0717 after correction. The Ratio of minimum to maximum transmission is 0.7892. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5469
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.832
_diffrn_reflns_theta_min         2.416
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1090
_reflns_number_total             1729
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.306
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1729
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1267
_refine_ls_R_factor_gt           0.0686
_refine_ls_restrained_S_all      1.030
_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)+(0.0651P)²+1.8099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1756
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N4(H4)
;
_atom_sites_solution_hydrogens   geom
_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
O4 O 0.9839(4) 0.4186(3) 0.7300(4) 0.0356(8) Uani 1 1 d . . . . .
O3 O 0.8765(4) 0.5550(3) 0.5574(4) 0.0353(8) Uani 1 1 d . . . . .
O1 O 0.5264(4) 0.6525(3) 0.4074(3) 0.0380(9) Uani 1 1 d . . . . .
O2 O 0.6773(4) 0.7683(3) 0.5901(4) 0.0476(10) Uani 1 1 d . . . . .
N4 N 0.6435(4) 0.4936(3) 0.8692(4) 0.0256(9) Uani 1 1 d . . . . .
H4 H 0.615195 0.467954 0.942978 0.031 Uiso 1 1 calc R . . . .
N5 N 0.3137(4) 0.6741(3) 0.6089(4) 0.0263(9) Uani 1 1 d . . . . .
N1 N 0.6122(4) 0.6771(3) 0.5452(4) 0.0280(9) Uani 1 1 d . . . . .
N2 N 0.8865(4) 0.4947(3) 0.6708(4) 0.0292(9) Uani 1 1 d . . . . .
N3 N 0.7714(4) 0.4563(3) 0.8542(4) 0.0250(9) Uani 1 1 d . . . . .
N8 N 0.0544(5) 0.7447(3) 0.5418(4) 0.0305(9) Uani 1 1 d . . . . .
N6 N 0.3473(4) 0.6043(3) 0.8507(4) 0.0291(9) Uani 1 1 d . . . . .
N7 N 0.2029(4) 0.6527(3) 0.7870(4) 0.0289(9) Uani 1 1 d . . . . .
N9 N -0.0577(5) 0.7864(4) 0.4605(5) 0.0374(10) Uani 1 1 d . . . . .
C2 C 0.6432(5) 0.5913(3) 0.6695(5) 0.0237(10) Uani 1 1 d . . . . .
C4 C 0.4092(5) 0.6186(4) 0.7417(5) 0.0231(10) Uani 1 1 d . . . . .
C3 C 0.5608(5) 0.5743(4) 0.7614(5) 0.0237(10) Uani 1 1 d . . . . .
C1 C 0.7699(5) 0.5160(4) 0.7307(5) 0.0255(10) Uani 1 1 d . . . . .
C5 C 0.1931(5) 0.6922(4) 0.6470(5) 0.0249(10) 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
O4 N2 1.226(5) . ?
O3 N2 1.232(5) . ?
O1 N1 1.210(4) . ?
O2 N1 1.218(5) . ?
N4 H4 0.8800 . ?
N4 N3 1.332(5) . ?
N4 C3 1.352(5) . ?
N5 C4 1.335(5) . ?
N5 C5 1.330(5) . ?
N1 C2 1.460(5) . ?
N2 C1 1.436(5) . ?
N3 C1 1.331(5) . ?
N8 N9 1.107(5) . ?
N8 C5 1.386(6) . ?
N6 N7 1.344(5) . ?
N6 C4 1.364(5) . ?
N7 C5 1.335(5) . ?
C2 C3 1.378(6) . ?
C2 C1 1.390(6) . ?
C4 C3 1.445(6) . ?
C4 C5 2.018(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 N4 H4 122.9 . . ?
N3 N4 C3 114.3(3) . . ?
C3 N4 H4 122.9 . . ?
C5 N5 C4 98.4(3) . . ?
O1 N1 O2 125.3(4) . . ?
O1 N1 C2 118.4(4) . . ?
O2 N1 C2 116.4(3) . . ?
O4 N2 O3 124.9(4) . . ?
O4 N2 C1 119.8(4) . . ?
O3 N2 C1 115.3(4) . . ?
C1 N3 N4 103.3(3) . . ?
N9 N8 C5 178.3(4) . . ?
N7 N6 C4 106.6(3) . . ?
C5 N7 N6 102.2(3) . . ?
C3 C2 N1 127.3(4) . . ?
C3 C2 C1 105.0(4) . . ?
C1 C2 N1 127.6(4) . . ?
N5 C4 N6 114.0(4) . . ?
N5 C4 C3 121.8(4) . . ?
N5 C4 C5 40.7(2) . . ?
N6 C4 C3 124.2(4) . . ?
N6 C4 C5 73.3(3) . . ?
C3 C4 C5 162.4(3) . . ?
N4 C3 C2 105.1(4) . . ?
N4 C3 C4 124.5(4) . . ?
C2 C3 C4 130.0(4) . . ?
N3 C1 N2 120.1(4) . . ?
N3 C1 C2 112.4(4) . . ?
C2 C1 N2 127.5(4) . . ?
N5 C5 N8 122.0(4) . . ?
N5 C5 N7 118.7(4) . . ?
N5 C5 C4 40.9(2) . . ?
N8 C5 C4 162.7(4) . . ?
N7 C5 N8 119.2(4) . . ?
N7 C5 C4 77.8(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_22019410_0m
_database_code_depnum_ccdc_archive 'CCDC 1918907'
loop_
_audit_author_name
_audit_author_address
'hualin xiong'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-07-19 deposited with the CCDC.	2022-09-20 downloaded from the CCDC.
;
_audit_creation_date             2022-07-19
_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         '3(H2 O), 2(C5 H5 N9 O4)'
_chemical_formula_sum            'C10 H16 N18 O11'
_chemical_formula_weight         564.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.7708(11)
_cell_length_b                   7.4519(4)
_cell_length_c                   16.5460(10)
_cell_angle_alpha                90
_cell_angle_beta                 110.017(2)
_cell_angle_gamma                90
_cell_volume                     2174.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3260
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.159
_cell_measurement_theta_min      2.309
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1276 before and 0.0678 after correction. The Ratio of minimum to maximum transmission is 0.8316. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11710
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.196
_diffrn_reflns_theta_min         2.310
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1657
_reflns_number_total             2189
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.289
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2189
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.047
_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)+(0.0464P)²+2.7955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1115
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2. Restrained distances
 O5-H5A = O5-H5A_$1
 0.84 with sigma of 0.02
3.a Rotating group:
 N7(H7A,H7B)
3.b X=CH2 refined with riding coordinates:
 N8(H8A,H8B)
;
_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
O5 O 0.500000 0.5395(4) 0.750000 0.0292(6) Uani 1 2 d DS T P . .
O1 O 0.11365(10) 0.5627(2) 0.38412(10) 0.0272(4) Uani 1 1 d . . . . .
O4 O 0.11005(10) 0.7770(2) 0.69686(10) 0.0304(4) Uani 1 1 d . . . . .
O3 O 0.03729(9) 0.6250(2) 0.58738(10) 0.0276(4) Uani 1 1 d . . . . .
O6 O 0.40094(10) 0.3318(3) 0.61990(11) 0.0282(4) Uani 1 1 d . . . . .
O2 O 0.06809(9) 0.7702(2) 0.44483(10) 0.0292(4) Uani 1 1 d . . . . .
N2 N 0.23633(10) 0.5481(2) 0.53376(11) 0.0191(4) Uani 1 1 d . . . . .
N6 N 0.33707(10) 0.6682(2) 0.80686(11) 0.0171(4) Uani 1 1 d . . . . .
N1 N 0.09935(11) 0.6824(3) 0.63298(12) 0.0209(4) Uani 1 1 d . . . . .
N3 N 0.27942(10) 0.5387(3) 0.61844(11) 0.0202(4) Uani 1 1 d . . . . .
N7 N 0.39064(10) 0.7657(3) 0.78353(12) 0.0210(4) Uani 1 1 d . . . . .
H7A H 0.419041 0.691242 0.766099 0.025 Uiso 1 1 d GR . . . .
H7B H 0.367300 0.840250 0.741306 0.025 Uiso 1 1 d GR . . . .
N4 N 0.23445(10) 0.5271(3) 0.80976(11) 0.0194(4) Uani 1 1 d . . . . .
N9 N 0.11221(10) 0.6469(3) 0.44704(12) 0.0204(4) Uani 1 1 d . . . . .
N5 N 0.28390(11) 0.5605(3) 0.89237(12) 0.0190(4) Uani 1 1 d . . . . .
N8 N 0.40525(11) 0.6989(3) 0.95519(11) 0.0228(5) Uani 1 1 d . . . . .
H8A H 0.407676 0.679273 1.008512 0.027 Uiso 1 1 calc R . . . .
H8B H 0.442684 0.754289 0.944957 0.027 Uiso 1 1 calc R . . . .
C1 C 0.34594(12) 0.6456(3) 0.89107(14) 0.0174(5) Uani 1 1 d . . . . .
C3 C 0.23707(12) 0.5906(3) 0.66571(13) 0.0176(5) Uani 1 1 d . . . . .
C2 C 0.26817(12) 0.5925(3) 0.75961(14) 0.0171(5) Uani 1 1 d . . . . .
C4 C 0.16437(12) 0.6330(3) 0.61081(13) 0.0167(5) Uani 1 1 d . . . . .
C5 C 0.16773(12) 0.6037(3) 0.52938(13) 0.0173(5) Uani 1 1 d . . . . .
H5 H 0.2735(15) 0.528(4) 0.9375(18) 0.035(8) Uiso 1 1 d . . . . .
H6A H 0.363(2) 0.391(5) 0.627(2) 0.057(10) Uiso 1 1 d . . . . .
H6B H 0.400(2) 0.220(6) 0.641(2) 0.090(14) Uiso 1 1 d . . . . .
H5A H 0.522(2) 0.473(5) 0.7952(18) 0.107(17) Uiso 1 1 d 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
O5 H5A 0.874(14) . ?
O5 H5A 0.874(14) 2_656 ?
O1 N9 1.223(2) . ?
O4 N1 1.228(2) . ?
O3 N1 1.228(2) . ?
O6 H6A 0.87(4) . ?
O6 H6B 0.91(5) . ?
O2 N9 1.229(2) . ?
N2 N3 1.359(2) . ?
N2 C5 1.331(3) . ?
N6 N7 1.398(2) . ?
N6 C1 1.356(3) . ?
N6 C2 1.382(3) . ?
N1 C4 1.437(3) . ?
N3 C3 1.349(3) . ?
N7 H7A 0.8832 . ?
N7 H7B 0.8829 . ?
N4 N5 1.387(3) . ?
N4 C2 1.298(3) . ?
N9 C5 1.440(3) . ?
N5 C1 1.333(3) . ?
N5 H5 0.87(3) . ?
N8 H8A 0.8800 . ?
N8 H8B 0.8800 . ?
N8 C1 1.309(3) . ?
C3 C2 1.461(3) . ?
C3 C4 1.392(3) . ?
C4 C5 1.388(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
H5A O5 H5A 111(6) . 2_656 ?
H6A O6 H6B 108(3) . . ?
C5 N2 N3 107.19(17) . . ?
C1 N6 N7 120.10(17) . . ?
C1 N6 C2 107.01(17) . . ?
C2 N6 N7 132.72(17) . . ?
O4 N1 C4 117.60(19) . . ?
O3 N1 O4 124.75(19) . . ?
O3 N1 C4 117.64(18) . . ?
C3 N3 N2 108.80(18) . . ?
N6 N7 H7A 109.6 . . ?
N6 N7 H7B 109.7 . . ?
H7A N7 H7B 109.2 . . ?
C2 N4 N5 104.73(18) . . ?
O1 N9 O2 124.66(19) . . ?
O1 N9 C5 118.11(19) . . ?
O2 N9 C5 117.19(18) . . ?
N4 N5 H5 121.7(19) . . ?
C1 N5 N4 111.30(18) . . ?
C1 N5 H5 127.0(19) . . ?
H8A N8 H8B 120.0 . . ?
C1 N8 H8A 120.0 . . ?
C1 N8 H8B 120.0 . . ?
N5 C1 N6 105.96(18) . . ?
N8 C1 N6 124.5(2) . . ?
N8 C1 N5 129.5(2) . . ?
N3 C3 C2 121.3(2) . . ?
N3 C3 C4 109.11(18) . . ?
C4 C3 C2 129.58(19) . . ?
N6 C2 C3 124.15(19) . . ?
N4 C2 N6 110.99(19) . . ?
N4 C2 C3 124.8(2) . . ?
C3 C4 N1 128.31(19) . . ?
C5 C4 N1 127.79(19) . . ?
C5 C4 C3 103.75(18) . . ?
N2 C5 N9 119.63(18) . . ?
N2 C5 C4 111.14(19) . . ?
C4 C5 N9 128.69(19) . . ?

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
N7 H7A O5 0.88 1.98 2.853(2) 167.8 . yes
N8 H8A O6 0.88 1.89 2.764(2) 170.5 6_566 yes
N5 H5 N2 0.87(3) 2.03(3) 2.891(3) 173(3) 6_566 yes
O6 H6A N3 0.87(4) 1.89(4) 2.747(3) 168(3) . yes
O5 H5A O6 0.874(14) 1.95(2) 2.784(2) 160(4) 2_656 yes


_olex2_submission_special_instructions 'No special instructions were received'
