# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_3c_170K
_database_code_depnum_ccdc_archive 'CCDC 2060884'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C7 H6 N2 O'
_chemical_formula_sum            'C7 H6 N2 O'
_chemical_formula_weight         134.14

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   3.79610(10)
_cell_length_b                   7.4931(3)
_cell_length_c                   22.9246(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.5201(13)
_cell_angle_gamma                90
_cell_volume                     643.10(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    1452
_cell_measurement_theta_min      2.864
_cell_measurement_theta_max      27.333

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      170.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD with APEXII detector'
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ scans + ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            1431
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.864
_diffrn_reflns_theta_max         27.333
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1431
_reflns_number_gt                1196
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0607P)²+0.3895P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_extinction_coef       0.028(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1431
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1432
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1A C 0.2418(5) 0.9064(2) 0.39011(9) 0.0352(5) Uani 1 1 d . . . . .
C2A C 0.4128(5) 0.7434(2) 0.40845(9) 0.0357(5) Uani 1 1 d . . . . .
C3A C 0.4748(5) 0.6258(2) 0.36390(9) 0.0344(5) Uani 1 1 d . . . . .
C4A C 0.3704(5) 0.6651(3) 0.30389(9) 0.0382(5) Uani 1 1 d . . . . .
H4A H 0.413839 0.582135 0.274550 0.046 Uiso 1 1 calc R U . . .
C5A C 0.2043(6) 0.8248(3) 0.28774(9) 0.0399(5) Uani 1 1 d . . . . .
H5A H 0.131195 0.852919 0.247135 0.048 Uiso 1 1 calc R U . . .
C6A C 0.1440(5) 0.9450(3) 0.33130(9) 0.0377(5) Uani 1 1 d . . . . .
H6A H 0.032731 1.056137 0.319986 0.045 Uiso 1 1 calc R U . . .
C7A C 0.6479(6) 0.4590(3) 0.38066(10) 0.0411(5) Uani 1 1 d . . . . .
N1A N 0.4949(6) 0.7047(3) 0.46744(8) 0.0551(6) Uani 1 1 d G . . . .
H1A1 H 0.683396 0.635540 0.479537 0.083 Uiso 1 1 d G U . . .
H1A2 H 0.491140 0.794101 0.492911 0.083 Uiso 1 1 d G U . . .
N2A N 0.7884(6) 0.3272(2) 0.39462(10) 0.0580(6) Uani 1 1 d . . . . .
O1A O 0.1827(4) 1.01648(19) 0.43489(7) 0.0486(5) Uani 1 1 d . . . . .
H1A H 0.059239 1.104134 0.420765 0.073 Uiso 1 1 calc 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
C1A O1A 1.364(2) . ?
C1A C6A 1.369(3) . ?
C1A C2A 1.414(3) . ?
C2A N1A 1.368(3) . ?
C2A C3A 1.398(3) . ?
C3A C4A 1.399(3) . ?
C3A C7A 1.435(3) . ?
C4A C5A 1.375(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.392(3) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A N2A 1.143(3) . ?
N1A H1A1 0.8900 . ?
N1A H1A2 0.8901 . ?
O1A H1A 0.8400 . ?

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
O1A C1A C6A 124.20(17) . . ?
O1A C1A C2A 115.02(17) . . ?
C6A C1A C2A 120.78(18) . . ?
N1A C2A C3A 123.40(18) . . ?
N1A C2A C1A 119.69(18) . . ?
C3A C2A C1A 116.85(18) . . ?
C2A C3A C4A 122.10(17) . . ?
C2A C3A C7A 118.59(18) . . ?
C4A C3A C7A 119.30(18) . . ?
C5A C4A C3A 119.39(18) . . ?
C5A C4A H4A 120.3 . . ?
C3A C4A H4A 120.3 . . ?
C4A C5A C6A 119.54(19) . . ?
C4A C5A H5A 120.2 . . ?
C6A C5A H5A 120.2 . . ?
C1A C6A C5A 121.33(18) . . ?
C1A C6A H6A 119.3 . . ?
C5A C6A H6A 119.3 . . ?
N2A C7A C3A 179.1(3) . . ?
C2A N1A H1A1 118.1 . . ?
C2A N1A H1A2 117.6 . . ?
H1A1 N1A H1A2 109.5 . . ?
C1A O1A H1A 109.5 . . ?

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
O1A C1A C2A N1A 2.0(3) . . . . ?
C6A C1A C2A N1A -177.3(2) . . . . ?
O1A C1A C2A C3A 179.29(18) . . . . ?
C6A C1A C2A C3A -0.1(3) . . . . ?
N1A C2A C3A C4A 176.5(2) . . . . ?
C1A C2A C3A C4A -0.7(3) . . . . ?
N1A C2A C3A C7A -2.9(3) . . . . ?
C1A C2A C3A C7A 179.96(18) . . . . ?
C2A C3A C4A C5A 0.6(3) . . . . ?
C7A C3A C4A C5A 179.97(19) . . . . ?
C3A C4A C5A C6A 0.2(3) . . . . ?
O1A C1A C6A C5A -178.4(2) . . . . ?
C2A C1A C6A C5A 0.9(3) . . . . ?
C4A C5A C6A C1A -1.0(3) . . . . ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.053

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
####################################################################### 
# 
# 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_8d_170K
_database_code_depnum_ccdc_archive 'CCDC 2060891'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C10 H16 N3 O 1+, Cl 1-, C2 H6 O'
_chemical_formula_sum            'C12 H22 Cl N3 O2'
_chemical_formula_weight         275.77

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   8.96920(10)
_cell_length_b                   18.2082(2)
_cell_length_c                   9.20580(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.4436(7)
_cell_angle_gamma                90
_cell_volume                     1441.93(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    170.0(1)
_cell_measurement_reflns_used    3540
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.878

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.720
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.265
_shelx_estimated_absorpt_T_min   0.832
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5125
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS 2008 (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      170.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD with APEXII detector'
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ scans + ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            27245
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.564
_diffrn_reflns_theta_max         28.037
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3461
_reflns_number_gt                2973
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+0.7093P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3461
_refine_ls_number_parameters     191
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0977
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.23058(4) 0.04646(2) 0.64336(4) 0.03360(11) Uani 1 1 d . . . . .
C1 C 0.67332(16) 0.08286(8) 0.76016(16) 0.0294(3) Uani 1 1 d . . . . .
C2 C 0.82523(16) 0.09752(8) 0.75340(16) 0.0263(3) Uani 1 1 d . . . . .
C3 C 0.94397(16) 0.10225(7) 0.88717(16) 0.0265(3) Uani 1 1 d . . . . .
H3 H 1.047263 0.110988 0.883497 0.032 Uiso 1 1 calc R U . . .
C4 C 0.91452(16) 0.09440(7) 1.02769(16) 0.0263(3) Uani 1 1 d . . . . .
C5 C 0.76250(17) 0.08144(9) 1.03229(17) 0.0318(3) Uani 1 1 d . . . . .
H5 H 0.740763 0.076804 1.127054 0.038 Uiso 1 1 calc R U . . .
C6 C 0.64332(17) 0.07534(9) 0.89902(17) 0.0337(3) Uani 1 1 d . . . . .
H6 H 0.540316 0.065925 0.902823 0.040 Uiso 1 1 calc R U . . .
C7 C 1.04298(16) 0.09655(7) 1.16903(16) 0.0267(3) Uani 1 1 d . . . . .
C8 C 1.31742(17) 0.13009(9) 1.29814(18) 0.0343(3) Uani 1 1 d . . . . .
H8 H 1.313104 0.087346 1.365029 0.041 Uiso 1 1 calc R U . . .
C9 C 1.4542(2) 0.11928(11) 1.2347(2) 0.0480(4) Uani 1 1 d . . . . .
H9A H 1.437322 0.075223 1.170936 0.072 Uiso 1 1 calc R U . . .
H9B H 1.549429 0.113449 1.318172 0.072 Uiso 1 1 calc R U . . .
H9C H 1.464278 0.162156 1.173825 0.072 Uiso 1 1 calc R U . . .
C10 C 1.3307(2) 0.19928(11) 1.3907(2) 0.0564(5) Uani 1 1 d . . . . .
H10A H 1.328066 0.242050 1.325392 0.085 Uiso 1 1 calc R U . . .
H10B H 1.429047 0.198836 1.471608 0.085 Uiso 1 1 calc R U . . .
H10C H 1.243803 0.201948 1.435303 0.085 Uiso 1 1 calc R U . . .
N1 N 0.85017(14) 0.10850(7) 0.61039(14) 0.0308(3) Uani 1 1 d G . . . .
H1A H 0.789986 0.079392 0.536395 0.046 Uiso 1 1 d G U . . .
H1B H 0.951797 0.102820 0.613382 0.046 Uiso 1 1 d G U . . .
N2 N 1.17301(14) 0.13078(7) 1.17190(14) 0.0313(3) Uani 1 1 d . . . . .
H2 H 1.173905 0.156415 1.091123 0.038 Uiso 1 1 calc R U . . .
N3 N 1.02564(15) 0.06321(7) 1.29067(14) 0.0309(3) Uani 1 1 d . . . . .
H3A H 1.101797 0.063637 1.375491 0.037 Uiso 1 1 calc R U . . .
H3B H 0.937940 0.040564 1.286866 0.037 Uiso 1 1 calc R U . . .
O1 O 0.56368(12) 0.07568(7) 0.62518(12) 0.0401(3) Uani 1 1 d . . . . .
H1 H 0.477861 0.065372 0.639982 0.060 Uiso 1 1 calc R U . . .
C1S C 0.7646(3) 0.26383(19) 0.3372(3) 0.0541(8) Uani 0.744(5) 1 d D U P A 1
H1S1 H 0.732481 0.313552 0.296869 0.065 Uiso 0.744(5) 1 calc R U P A 1
H1S2 H 0.702031 0.227621 0.265033 0.065 Uiso 0.744(5) 1 calc R U P A 1
C2S C 0.9314(4) 0.25303(16) 0.3489(4) 0.0581(9) Uani 0.744(5) 1 d D U P A 1
H2S1 H 0.993900 0.288420 0.421088 0.087 Uiso 0.744(5) 1 calc R U P A 1
H2S2 H 0.948263 0.260533 0.249256 0.087 Uiso 0.744(5) 1 calc R U P A 1
H2S3 H 0.962409 0.203003 0.383916 0.087 Uiso 0.744(5) 1 calc R U P A 1
O1S O 0.73374(15) 0.25558(7) 0.48202(15) 0.0440(3) Uani 1 1 d D U . . .
H1S H 0.765568 0.214338 0.518842 0.066 Uiso 1 1 calc R U . A 1
C1S' C 0.8469(10) 0.2783(5) 0.4086(9) 0.054(2) Uani 0.256(5) 1 d D U P A 2
H1S3 H 0.952089 0.265281 0.472744 0.065 Uiso 0.256(5) 1 calc R U P A 2
H1S4 H 0.842325 0.332349 0.395872 0.065 Uiso 0.256(5) 1 calc R U P A 2
C2S' C 0.8192(12) 0.2431(6) 0.2598(9) 0.067(3) Uani 0.256(5) 1 d D U P A 2
H2S4 H 0.820953 0.189658 0.272044 0.100 Uiso 0.256(5) 1 calc R U P A 2
H2S5 H 0.900596 0.257948 0.213777 0.100 Uiso 0.256(5) 1 calc R U P A 2
H2S6 H 0.717539 0.258341 0.194260 0.100 Uiso 0.256(5) 1 calc R U P A 2


_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
C1 O1 1.3551(17) . ?
C1 C6 1.386(2) . ?
C1 C2 1.4069(19) . ?
C2 C3 1.3840(19) . ?
C2 N1 1.4107(18) . ?
C3 C4 1.399(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(2) . ?
C4 C7 1.4743(19) . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N2 1.3160(18) . ?
C7 N3 1.3211(18) . ?
C8 N2 1.4751(18) . ?
C8 C10 1.506(3) . ?
C8 C9 1.513(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N2 H2 0.8800 . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
O1 H1 0.8400 . ?
C1S O1S 1.444(3) . ?
C1S C2S 1.482(4) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 0.9800 . ?
O1S C1S' 1.431(6) . ?
O1S H1S 0.8400 . ?
C1S' C2S' 1.468(8) . ?
C1S' H1S3 0.9900 . ?
C1S' H1S4 0.9900 . ?
C2S' H2S4 0.9800 . ?
C2S' H2S5 0.9800 . ?
C2S' H2S6 0.9800 . ?

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
O1 C1 C6 123.80(13) . . ?
O1 C1 C2 116.00(13) . . ?
C6 C1 C2 120.19(13) . . ?
C3 C2 C1 118.91(13) . . ?
C3 C2 N1 122.42(12) . . ?
C1 C2 N1 118.65(13) . . ?
C2 C3 C4 121.14(13) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.14(13) . . ?
C5 C4 C7 120.25(13) . . ?
C3 C4 C7 120.56(12) . . ?
C6 C5 C4 120.15(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.44(13) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N2 C7 N3 121.12(13) . . ?
N2 C7 C4 119.81(13) . . ?
N3 C7 C4 119.06(12) . . ?
N2 C8 C10 110.48(14) . . ?
N2 C8 C9 108.89(13) . . ?
C10 C8 C9 112.58(15) . . ?
N2 C8 H8 108.3 . . ?
C10 C8 H8 108.3 . . ?
C9 C8 H8 108.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 N1 H1A 113.5 . . ?
C2 N1 H1B 112.2 . . ?
H1A N1 H1B 109.5 . . ?
C7 N2 C8 125.97(13) . . ?
C7 N2 H2 117.0 . . ?
C8 N2 H2 117.0 . . ?
C7 N3 H3A 120.0 . . ?
C7 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C1 O1 H1 109.5 . . ?
O1S C1S C2S 111.9(2) . . ?
O1S C1S H1S1 109.2 . . ?
C2S C1S H1S1 109.2 . . ?
O1S C1S H1S2 109.2 . . ?
C2S C1S H1S2 109.2 . . ?
H1S1 C1S H1S2 107.9 . . ?
C1S C2S H2S1 109.5 . . ?
C1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
C1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
C1S O1S H1S 109.5 . . ?
O1S C1S' C2S' 111.0(7) . . ?
O1S C1S' H1S3 109.4 . . ?
C2S' C1S' H1S3 109.4 . . ?
O1S C1S' H1S4 109.4 . . ?
C2S' C1S' H1S4 109.4 . . ?
H1S3 C1S' H1S4 108.0 . . ?
C1S' C2S' H2S4 109.5 . . ?
C1S' C2S' H2S5 109.5 . . ?
H2S4 C2S' H2S5 109.5 . . ?
C1S' C2S' H2S6 109.5 . . ?
H2S4 C2S' H2S6 109.5 . . ?
H2S5 C2S' H2S6 109.5 . . ?

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 C1 C2 C3 -177.17(13) . . . . ?
C6 C1 C2 C3 1.7(2) . . . . ?
O1 C1 C2 N1 4.3(2) . . . . ?
C6 C1 C2 N1 -176.85(14) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
N1 C2 C3 C4 177.05(13) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C2 C3 C4 C7 177.49(13) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C7 C4 C5 C6 -176.37(14) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
O1 C1 C6 C5 178.18(15) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
C5 C4 C7 N2 -158.33(14) . . . . ?
C3 C4 C7 N2 24.3(2) . . . . ?
C5 C4 C7 N3 22.4(2) . . . . ?
C3 C4 C7 N3 -154.99(14) . . . . ?
N3 C7 N2 C8 7.1(2) . . . . ?
C4 C7 N2 C8 -172.15(13) . . . . ?
C10 C8 N2 C7 -99.85(19) . . . . ?
C9 C8 N2 C7 136.02(16) . . . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.042

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_8b_123K
_database_code_depnum_ccdc_archive 'CCDC 2060888'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C18 H23 N6 O2 1+, Cl 1-, 4(H2 O)'
_chemical_formula_sum            'C18 H31 Cl N6 O6'
_chemical_formula_weight         462.94

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   20.1831(3)
_cell_length_b                   7.18245(12)
_cell_length_c                   30.4640(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.6637(17)
_cell_angle_gamma                90
_cell_volume                     4308.76(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    123.0(1)
_cell_measurement_reflns_used    4521
_cell_measurement_theta_min      4.7960
_cell_measurement_theta_max      74.1660

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.313
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    1.994
_shelx_estimated_absorpt_T_min   0.574
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
 (compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
 model based on expressions derived by R.C. Clark & J.S. Reid.
 (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      123.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.1977
_diffrn_reflns_number            7054
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         4.813
_diffrn_reflns_theta_max         74.334
_diffrn_reflns_theta_full        67.750
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4185
_reflns_number_gt                3694
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1151P)²+6.8009P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4185
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1899
_refine_ls_wR_factor_gt          0.1830
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O1W O 0.33911(10) 0.2107(3) 0.37174(8) 0.0473(5) Uani 1 1 d G . . . .
H11W H 0.321562 0.101041 0.368913 0.071 Uiso 1 1 d G U . . .
H12W H 0.382657 0.201882 0.377467 0.071 Uiso 1 1 d G U . . .
O2W O 0.23735(10) 0.4039(3) 0.39493(7) 0.0507(5) Uani 1 1 d G . . . .
H21W H 0.263111 0.331221 0.383623 0.076 Uiso 1 1 d G U . . .
H22W H 0.227557 0.351856 0.418117 0.076 Uiso 1 1 d G U . . .
O3W O 0.66120(9) 0.2871(3) 0.37850(7) 0.0458(5) Uani 1 1 d G . . . .
H31W H 0.672945 0.401905 0.382737 0.069 Uiso 1 1 d G U . . .
H32W H 0.617819 0.277878 0.374647 0.069 Uiso 1 1 d G U . . .
O4W O 0.76561(9) 0.0989(3) 0.35566(6) 0.0451(5) Uani 1 1 d G . . . .
H41W H 0.728752 0.140418 0.361853 0.068 Uiso 1 1 d G U . . .
H42W H 0.770248 0.144600 0.330408 0.068 Uiso 1 1 d G U . . .
Cl1 Cl 0.50115(2) 0.24822(7) 0.37630(2) 0.0227(2) Uani 1 1 d . . . . .
C1A C 0.64347(9) 0.2101(3) 0.22144(7) 0.0185(4) Uani 1 1 d . . . . .
C2A C 0.59104(9) 0.1639(3) 0.18405(6) 0.0178(4) Uani 1 1 d . . . . .
C3A C 0.52400(9) 0.1721(3) 0.18794(6) 0.0183(4) Uani 1 1 d . . . . .
H3A H 0.488740 0.144854 0.162528 0.022 Uiso 1 1 calc R U . . .
C4A C 0.50744(10) 0.2199(3) 0.22883(7) 0.0177(4) Uani 1 1 d . . . . .
C5A C 0.55924(10) 0.2580(3) 0.26610(7) 0.0187(4) Uani 1 1 d . . . . .
H5A H 0.548530 0.286686 0.294188 0.022 Uiso 1 1 calc R U . . .
C6A C 0.62647(10) 0.2543(3) 0.26231(7) 0.0190(4) Uani 1 1 d . . . . .
H6A H 0.661459 0.282183 0.287829 0.023 Uiso 1 1 calc R U . . .
C7A C 0.43651(10) 0.2230(3) 0.23240(7) 0.0182(4) Uani 1 1 d . . . . .
C8A C 0.31963(10) 0.2297(3) 0.21199(8) 0.0271(5) Uani 1 1 d . . . . .
H8A1 H 0.290102 0.122519 0.200421 0.033 Uiso 1 1 calc R U . . .
H8A2 H 0.295136 0.346696 0.201746 0.033 Uiso 1 1 calc R U . . .
C9A C 0.34214(10) 0.2236(3) 0.26349(7) 0.0233(5) Uani 1 1 d . . . . .
H9A1 H 0.325378 0.333502 0.277407 0.028 Uiso 1 1 calc R U . . .
H9A2 H 0.325913 0.108962 0.275803 0.028 Uiso 1 1 calc R U . . .
H1A H 0.750000 0.250000 0.250000 0.10(2) Uiso 1 2 d S . P . .
N1A N 0.60783(8) 0.1107(2) 0.14333(5) 0.0210(4) Uani 1 1 d G . . . .
H1A1 H 0.578859 0.020908 0.129456 0.032 Uiso 1 1 d G U . . .
H1A2 H 0.650958 0.065259 0.149833 0.032 Uiso 1 1 d G U . . .
N2A N 0.38421(8) 0.2199(3) 0.19760(6) 0.0214(4) Uani 1 1 d . . . . .
H2A H 0.387733 0.212963 0.169360 0.026 Uiso 1 1 calc R U . . .
N3A N 0.41637(9) 0.2254(2) 0.27072(6) 0.0217(4) Uani 1 1 d . . . . .
H3A1 H 0.444101 0.227862 0.297399 0.026 Uiso 1 1 calc R U . . .
O1A O 0.70779(7) 0.2032(2) 0.21666(5) 0.0243(3) Uani 1 1 d . . . . .
C1B C 0.35746(10) 0.2256(3) 0.53073(7) 0.0198(4) Uani 1 1 d . . . . .
C2B C 0.40979(9) 0.1774(3) 0.56817(6) 0.0191(4) Uani 1 1 d . . . . .
C3B C 0.47698(9) 0.1853(3) 0.56451(6) 0.0189(4) Uani 1 1 d . . . . .
H3B H 0.512080 0.155186 0.589792 0.023 Uiso 1 1 calc R U . . .
C4B C 0.49377(10) 0.2372(3) 0.52379(7) 0.0180(4) Uani 1 1 d . . . . .
C5B C 0.44218(10) 0.2806(3) 0.48674(7) 0.0201(4) Uani 1 1 d . . . . .
H5B H 0.453173 0.313852 0.459004 0.024 Uiso 1 1 calc R U . . .
C6B C 0.37485(10) 0.2753(3) 0.49018(7) 0.0209(4) Uani 1 1 d . . . . .
H6B H 0.340057 0.305710 0.464749 0.025 Uiso 1 1 calc R U . . .
C7B C 0.56452(10) 0.2364(3) 0.52010(7) 0.0175(4) Uani 1 1 d . . . . .
C8B C 0.68137(10) 0.2165(3) 0.53991(7) 0.0248(5) Uani 1 1 d . . . . .
H8B1 H 0.702639 0.092587 0.546673 0.030 Uiso 1 1 calc R U . . .
H8B2 H 0.713695 0.313743 0.554293 0.030 Uiso 1 1 calc R U . . .
C9B C 0.65879(10) 0.2483(3) 0.48893(7) 0.0217(5) Uani 1 1 d . . . . .
H9B1 H 0.674117 0.371083 0.480195 0.026 Uiso 1 1 calc R U . . .
H9B2 H 0.676301 0.149480 0.471862 0.026 Uiso 1 1 calc R U . . .
H1B H 0.250000 0.218(9) 0.500000 0.08(2) Uiso 1 2 d S . P . .
N1B N 0.39263(8) 0.1199(2) 0.60861(5) 0.0218(4) Uani 1 1 d G . . . .
H1B1 H 0.421418 0.029088 0.622112 0.033 Uiso 1 1 d G U . . .
H1B2 H 0.349318 0.075739 0.602344 0.033 Uiso 1 1 d G U . . .
N2B N 0.61709(9) 0.2288(3) 0.55472(6) 0.0216(4) Uani 1 1 d . . . . .
H2B H 0.613892 0.230970 0.583067 0.026 Uiso 1 1 calc R U . . .
N3B N 0.58460(9) 0.2404(2) 0.48167(6) 0.0204(4) Uani 1 1 d . . . . .
H3B1 H 0.556868 0.238471 0.454996 0.024 Uiso 1 1 calc R U . . .
O1B O 0.29303(7) 0.2135(2) 0.53498(5) 0.0257(4) 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
O1W H11W 0.8600 . ?
O1W H12W 0.8600 . ?
O2W H21W 0.8601 . ?
O2W H22W 0.8597 . ?
O3W H31W 0.8600 . ?
O3W H32W 0.8600 . ?
O4W H41W 0.8600 . ?
O4W H42W 0.8600 . ?
C1A O1A 1.339(2) . ?
C1A C6A 1.398(3) . ?
C1A C2A 1.414(3) . ?
C2A C3A 1.385(2) . ?
C2A N1A 1.409(2) . ?
C3A C4A 1.401(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.392(3) . ?
C4A C7A 1.459(3) . ?
C5A C6A 1.387(3) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A N3A 1.318(3) . ?
C7A N2A 1.322(3) . ?
C8A N2A 1.465(2) . ?
C8A C9A 1.535(3) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A N3A 1.466(3) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
N1A H1A1 0.9100 . ?
N1A H1A2 0.9099 . ?
N2A H2A 0.8800 . ?
N3A H3A1 0.8800 . ?
O1A H1A 1.2210(13) . ?
C1B O1B 1.337(2) . ?
C1B C6B 1.402(3) . ?
C1B C2B 1.417(3) . ?
C2B C3B 1.386(3) . ?
C2B N1B 1.412(2) . ?
C3B C4B 1.406(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.393(3) . ?
C4B C7B 1.457(3) . ?
C5B C6B 1.386(3) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B N3B 1.321(3) . ?
C7B N2B 1.323(3) . ?
C8B N2B 1.467(2) . ?
C8B C9B 1.537(3) . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9B N3B 1.466(3) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
N1B H1B1 0.9099 . ?
N1B H1B2 0.9100 . ?
N2B H2B 0.8800 . ?
N3B H3B1 0.8800 . ?
O1B H1B 1.219(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
H11W O1W H12W 109.5 . . ?
H21W O2W H22W 109.5 . . ?
H31W O3W H32W 109.5 . . ?
H41W O4W H42W 109.5 . . ?
O1A C1A C6A 122.57(17) . . ?
O1A C1A C2A 118.43(17) . . ?
C6A C1A C2A 118.96(17) . . ?
C3A C2A N1A 121.01(16) . . ?
C3A C2A C1A 119.58(17) . . ?
N1A C2A C1A 119.42(16) . . ?
C2A C3A C4A 120.95(16) . . ?
C2A C3A H3A 119.5 . . ?
C4A C3A H3A 119.5 . . ?
C5A C4A C3A 119.38(18) . . ?
C5A C4A C7A 120.66(18) . . ?
C3A C4A C7A 119.93(17) . . ?
C6A C5A C4A 120.12(18) . . ?
C6A C5A H5A 119.9 . . ?
C4A C5A H5A 119.9 . . ?
C5A C6A C1A 120.92(18) . . ?
C5A C6A H6A 119.5 . . ?
C1A C6A H6A 119.5 . . ?
N3A C7A N2A 111.31(17) . . ?
N3A C7A C4A 124.35(18) . . ?
N2A C7A C4A 124.32(18) . . ?
N2A C8A C9A 102.77(16) . . ?
N2A C8A H8A1 111.2 . . ?
C9A C8A H8A1 111.2 . . ?
N2A C8A H8A2 111.2 . . ?
C9A C8A H8A2 111.2 . . ?
H8A1 C8A H8A2 109.1 . . ?
N3A C9A C8A 102.54(16) . . ?
N3A C9A H9A1 111.3 . . ?
C8A C9A H9A1 111.3 . . ?
N3A C9A H9A2 111.3 . . ?
C8A C9A H9A2 111.3 . . ?
H9A1 C9A H9A2 109.2 . . ?
C2A N1A H1A1 110.3 . . ?
C2A N1A H1A2 108.0 . . ?
H1A1 N1A H1A2 109.5 . . ?
C7A N2A C8A 111.44(17) . . ?
C7A N2A H2A 124.3 . . ?
C8A N2A H2A 124.3 . . ?
C7A N3A C9A 111.73(17) . . ?
C7A N3A H3A1 124.1 . . ?
C9A N3A H3A1 124.1 . . ?
C1A O1A H1A 114.56(13) . . ?
O1B C1B C6B 122.56(18) . . ?
O1B C1B C2B 118.37(18) . . ?
C6B C1B C2B 119.00(18) . . ?
C3B C2B N1B 120.90(16) . . ?
C3B C2B C1B 119.68(17) . . ?
N1B C2B C1B 119.42(17) . . ?
C2B C3B C4B 120.74(17) . . ?
C2B C3B H3B 119.6 . . ?
C4B C3B H3B 119.6 . . ?
C5B C4B C3B 119.49(18) . . ?
C5B C4B C7B 120.64(18) . . ?
C3B C4B C7B 119.79(17) . . ?
C6B C5B C4B 120.25(19) . . ?
C6B C5B H5B 119.9 . . ?
C4B C5B H5B 119.9 . . ?
C5B C6B C1B 120.82(18) . . ?
C5B C6B H6B 119.6 . . ?
C1B C6B H6B 119.6 . . ?
N3B C7B N2B 111.05(18) . . ?
N3B C7B C4B 124.40(18) . . ?
N2B C7B C4B 124.54(18) . . ?
N2B C8B C9B 102.45(16) . . ?
N2B C8B H8B1 111.3 . . ?
C9B C8B H8B1 111.3 . . ?
N2B C8B H8B2 111.3 . . ?
C9B C8B H8B2 111.3 . . ?
H8B1 C8B H8B2 109.2 . . ?
N3B C9B C8B 102.33(16) . . ?
N3B C9B H9B1 111.3 . . ?
C8B C9B H9B1 111.3 . . ?
N3B C9B H9B2 111.3 . . ?
C8B C9B H9B2 111.3 . . ?
H9B1 C9B H9B2 109.2 . . ?
C2B N1B H1B1 110.5 . . ?
C2B N1B H1B2 109.1 . . ?
H1B1 N1B H1B2 109.5 . . ?
C7B N2B C8B 111.48(17) . . ?
C7B N2B H2B 124.3 . . ?
C8B N2B H2B 124.3 . . ?
C7B N3B C9B 111.65(17) . . ?
C7B N3B H3B1 124.2 . . ?
C9B N3B H3B1 124.2 . . ?
C1B O1B H1B 115.8(3) . . ?

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
O1A C1A C2A C3A -179.23(17) . . . . ?
C6A C1A C2A C3A 3.1(3) . . . . ?
O1A C1A C2A N1A 0.6(3) . . . . ?
C6A C1A C2A N1A -177.06(18) . . . . ?
N1A C2A C3A C4A 178.19(18) . . . . ?
C1A C2A C3A C4A -2.0(3) . . . . ?
C2A C3A C4A C5A -0.6(3) . . . . ?
C2A C3A C4A C7A -178.43(17) . . . . ?
C3A C4A C5A C6A 2.0(3) . . . . ?
C7A C4A C5A C6A 179.85(17) . . . . ?
C4A C5A C6A C1A -0.9(3) . . . . ?
O1A C1A C6A C5A -179.26(18) . . . . ?
C2A C1A C6A C5A -1.7(3) . . . . ?
C5A C4A C7A N3A -13.4(3) . . . . ?
C3A C4A C7A N3A 164.42(19) . . . . ?
C5A C4A C7A N2A 167.97(19) . . . . ?
C3A C4A C7A N2A -14.2(3) . . . . ?
N2A C8A C9A N3A 4.1(2) . . . . ?
N3A C7A N2A C8A 2.9(2) . . . . ?
C4A C7A N2A C8A -178.36(18) . . . . ?
C9A C8A N2A C7A -4.4(2) . . . . ?
N2A C7A N3A C9A 0.2(2) . . . . ?
C4A C7A N3A C9A -178.64(18) . . . . ?
C8A C9A N3A C7A -2.8(2) . . . . ?
O1B C1B C2B C3B 178.82(18) . . . . ?
C6B C1B C2B C3B 1.8(3) . . . . ?
O1B C1B C2B N1B -0.4(3) . . . . ?
C6B C1B C2B N1B -177.47(18) . . . . ?
N1B C2B C3B C4B 178.10(18) . . . . ?
C1B C2B C3B C4B -1.2(3) . . . . ?
C2B C3B C4B C5B -0.2(3) . . . . ?
C2B C3B C4B C7B -177.23(17) . . . . ?
C3B C4B C5B C6B 1.0(3) . . . . ?
C7B C4B C5B C6B 177.95(18) . . . . ?
C4B C5B C6B C1B -0.3(3) . . . . ?
O1B C1B C6B C5B -177.96(19) . . . . ?
C2B C1B C6B C5B -1.1(3) . . . . ?
C5B C4B C7B N3B -13.2(3) . . . . ?
C3B C4B C7B N3B 163.71(19) . . . . ?
C5B C4B C7B N2B 167.77(19) . . . . ?
C3B C4B C7B N2B -15.3(3) . . . . ?
N2B C8B C9B N3B -9.7(2) . . . . ?
N3B C7B N2B C8B -3.2(2) . . . . ?
C4B C7B N2B C8B 175.87(18) . . . . ?
C9B C8B N2B C7B 8.4(2) . . . . ?
N2B C7B N3B C9B -3.9(2) . . . . ?
C4B C7B N3B C9B 176.95(17) . . . . ?
C8B C9B N3B C7B 8.8(2) . . . . ?

_refine_diff_density_max         1.240
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.085

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_8a_II_223K
_database_code_depnum_ccdc_archive 'CCDC 2060886'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C14 H19 N6 O2 1+, Cl 1-, 2(H2 O)'
_chemical_formula_sum            'C14 H23 Cl N6 O4'
_chemical_formula_weight         374.83

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5903(2)
_cell_length_b                   14.7776(4)
_cell_length_c                   15.1797(4)
_cell_angle_alpha                87.837(2)
_cell_angle_beta                 73.679(2)
_cell_angle_gamma                82.100(2)
_cell_volume                     1831.77(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    223.0(1)
_cell_measurement_reflns_used    10740
_cell_measurement_theta_min      2.9930
_cell_measurement_theta_max      76.1440

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.785
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.067
_exptl_absorpt_coefficient_mu    2.133
_shelx_estimated_absorpt_T_min   0.285
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.478
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
 model based on expressions derived by R.C. Clark & J.S. Reid.
 (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      223.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.1977
_diffrn_reflns_number            14914
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.019
_diffrn_reflns_theta_max         76.510
_diffrn_reflns_theta_full        67.750
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7457
_reflns_number_gt                7125
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0810P)²+0.4379P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7457
_refine_ls_number_parameters     484
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1209
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.29455(7) 0.45008(3) 0.13068(4) 0.03764(14) Uani 1 1 d . . . . .
Cl2 Cl 0.57865(7) 0.05102(3) 0.62729(4) 0.03909(15) Uani 1 1 d . . . . .
O1W O 0.9025(2) 0.42521(12) 0.15418(13) 0.0438(4) Uani 1 1 d G . . . .
H11W H 0.829790 0.448598 0.127873 0.066 Uiso 1 1 d G U . . .
H12W H 0.982452 0.457169 0.141121 0.066 Uiso 1 1 d G U . . .
O2W O 0.6610(2) 0.49803(13) 0.07413(12) 0.0442(4) Uani 1 1 d G . . . .
H21W H 0.690392 0.504649 0.015488 0.066 Uiso 1 1 d G U . . .
H22W H 0.567609 0.478088 0.090660 0.066 Uiso 1 1 d G U . . .
O3W O 0.7325(2) 0.00292(13) 0.42127(12) 0.0447(4) Uani 1 1 d G . . . .
H31W H 0.708889 0.007529 0.479997 0.067 Uiso 1 1 d G U . . .
H32W H 0.650088 -0.012093 0.406324 0.067 Uiso 1 1 d G U . . .
O4W O 0.9505(2) 0.07568(13) 0.65992(14) 0.0468(4) Uani 1 1 d G . . . .
H41W H 1.049306 0.050995 0.635391 0.070 Uiso 1 1 d G U . . .
H42W H 0.883407 0.041380 0.650719 0.070 Uiso 1 1 d G U . . .
H1AB H 0.263(5) 0.4915(7) 0.494(3) 0.080(12) Uiso 1 1 d D . . . .
C1A C 0.1892(2) 0.37607(12) 0.56995(12) 0.0214(3) Uani 1 1 d . . . . .
C2A C 0.2407(2) 0.28750(12) 0.59956(12) 0.0201(3) Uani 1 1 d . . . . .
C3A C 0.1485(2) 0.25112(13) 0.67919(13) 0.0227(3) Uani 1 1 d . . . . .
H3A H 0.181473 0.191715 0.697318 0.027 Uiso 1 1 calc R U . . .
C4A C 0.0059(2) 0.30221(13) 0.73327(12) 0.0228(3) Uani 1 1 d . . . . .
C5A C -0.0433(2) 0.38969(13) 0.70488(13) 0.0260(4) Uani 1 1 d . . . . .
H5A H -0.138464 0.424400 0.740778 0.031 Uiso 1 1 calc R U . . .
C6A C 0.0471(2) 0.42575(13) 0.62413(14) 0.0259(4) Uani 1 1 d . . . . .
H6A H 0.012042 0.484616 0.605609 0.031 Uiso 1 1 calc R U . . .
C7A C -0.0925(2) 0.26461(14) 0.81858(13) 0.0254(4) Uani 1 1 d . . . . .
N1A N 0.38464(19) 0.23963(11) 0.54264(11) 0.0243(3) Uani 1 1 d G . . . .
H1A1 H 0.435888 0.194273 0.569595 0.037 Uiso 1 1 d G U . . .
H1A2 H 0.453139 0.280977 0.519358 0.037 Uiso 1 1 d G U . . .
N2A N -0.0932(2) 0.17579(12) 0.82942(12) 0.0313(4) Uani 1 1 d . . . . .
H2A1 H -0.151084 0.154285 0.880474 0.038 Uiso 1 1 calc R U . . .
H2A2 H -0.035885 0.138634 0.785526 0.038 Uiso 1 1 calc R U . . .
N3A N -0.1795(2) 0.32093(13) 0.88522(12) 0.0357(4) Uani 1 1 d . . . . .
H3A1 H -0.237363 0.299375 0.936260 0.043 Uiso 1 1 calc R U . . .
H3A2 H -0.179104 0.379596 0.878114 0.043 Uiso 1 1 calc R U . . .
O1A O 0.27935(17) 0.40750(9) 0.49175(9) 0.0266(3) Uani 1 1 d D . . . .
C1B C 0.3303(2) 0.61058(12) 0.41975(13) 0.0218(3) Uani 1 1 d . . . . .
C2B C 0.2716(2) 0.69884(12) 0.39415(12) 0.0206(3) Uani 1 1 d . . . . .
C3B C 0.3585(2) 0.73876(12) 0.31516(13) 0.0227(3) Uani 1 1 d . . . . .
H3B H 0.319361 0.797621 0.298594 0.027 Uiso 1 1 calc R U . . .
C4B C 0.5036(2) 0.69284(13) 0.25970(12) 0.0233(4) Uani 1 1 d . . . . .
C5B C 0.5613(2) 0.60487(13) 0.28425(13) 0.0263(4) Uani 1 1 d . . . . .
H5B H 0.658603 0.573299 0.246983 0.032 Uiso 1 1 calc R U . . .
C6B C 0.4748(2) 0.56444(13) 0.36351(14) 0.0261(4) Uani 1 1 d . . . . .
H6B H 0.513753 0.505341 0.379543 0.031 Uiso 1 1 calc R U . . .
C7B C 0.5987(2) 0.73736(14) 0.17788(13) 0.0258(4) Uani 1 1 d . . . . .
N1B N 0.1275(2) 0.74468(11) 0.45306(11) 0.0254(3) Uani 1 1 d G . . . .
H1B1 H 0.057194 0.704512 0.477420 0.038 Uiso 1 1 d G U . . .
H1B2 H 0.076228 0.791412 0.427731 0.038 Uiso 1 1 d G U . . .
N2B N 0.5937(2) 0.82729(12) 0.17513(12) 0.0315(4) Uani 1 1 d . . . . .
H2B1 H 0.650012 0.853453 0.126529 0.038 Uiso 1 1 calc R U . . .
H2B2 H 0.534161 0.860262 0.221917 0.038 Uiso 1 1 calc R U . . .
N3B N 0.6881(2) 0.68712(13) 0.10766(12) 0.0343(4) Uani 1 1 d . . . . .
H3B1 H 0.744683 0.712897 0.058874 0.041 Uiso 1 1 calc R U . . .
H3B2 H 0.690905 0.628023 0.109866 0.041 Uiso 1 1 calc R U . . .
O1B O 0.24361(18) 0.57494(9) 0.49741(9) 0.0270(3) Uani 1 1 d D . . . .
H1CD H 0.250(6) -0.0064(7) -0.003(3) 0.105(16) Uiso 1 1 d D . . . .
C1C C 0.2518(2) 0.11079(12) 0.06981(12) 0.0216(3) Uani 1 1 d . . . . .
C2C C 0.1658(2) 0.19773(12) 0.09933(12) 0.0204(3) Uani 1 1 d . . . . .
C3C C 0.1762(2) 0.23571(12) 0.17914(12) 0.0212(3) Uani 1 1 d . . . . .
H3C H 0.118787 0.293684 0.198258 0.025 Uiso 1 1 calc R U . . .
C4C C 0.2717(2) 0.18835(13) 0.23169(13) 0.0226(3) Uani 1 1 d . . . . .
C5C C 0.3569(2) 0.10242(13) 0.20238(13) 0.0253(4) Uani 1 1 d . . . . .
H5C H 0.421750 0.070273 0.236917 0.030 Uiso 1 1 calc R U . . .
C6C C 0.3462(2) 0.06440(13) 0.12271(14) 0.0259(4) Uani 1 1 d . . . . .
H6C H 0.403529 0.006329 0.103939 0.031 Uiso 1 1 calc R U . . .
C7C C 0.2844(2) 0.22913(13) 0.31569(13) 0.0248(4) Uani 1 1 d . . . . .
N1C N 0.07483(19) 0.24434(11) 0.04324(11) 0.0246(3) Uani 1 1 d G . . . .
H1C1 H -0.005135 0.286081 0.075573 0.037 Uiso 1 1 d G U . . .
H1C2 H 0.030505 0.203466 0.018611 0.037 Uiso 1 1 d G U . . .
N2C N 0.2622(2) 0.31893(12) 0.32575(12) 0.0314(4) Uani 1 1 d . . . . .
H2C1 H 0.269360 0.342755 0.375796 0.038 Uiso 1 1 calc R U . . .
H2C2 H 0.240558 0.354168 0.282323 0.038 Uiso 1 1 calc R U . . .
N3C N 0.3173(3) 0.17556(12) 0.38137(12) 0.0344(4) Uani 1 1 d . . . . .
H3C1 H 0.324470 0.199244 0.431471 0.041 Uiso 1 1 calc R U . . .
H3C2 H 0.331845 0.116521 0.374622 0.041 Uiso 1 1 calc R U . . .
O1C O 0.23859(18) 0.07715(9) -0.00806(9) 0.0265(3) Uani 1 1 d D . . . .
C1D C 0.2588(2) -0.12526(12) -0.07775(12) 0.0216(3) Uani 1 1 d . . . . .
C2D C 0.3386(2) -0.21498(12) -0.10279(12) 0.0214(3) Uani 1 1 d . . . . .
C3D C 0.3277(2) -0.25480(12) -0.18134(12) 0.0223(3) Uani 1 1 d . . . . .
H3D H 0.377438 -0.315047 -0.196461 0.027 Uiso 1 1 calc R U . . .
C4D C 0.2430(2) -0.20607(13) -0.23895(12) 0.0236(4) Uani 1 1 d . . . . .
C5D C 0.1686(2) -0.11676(14) -0.21567(13) 0.0260(4) Uani 1 1 d . . . . .
H5D H 0.113633 -0.083356 -0.254477 0.031 Uiso 1 1 calc R U . . .
C6D C 0.1752(2) -0.07707(13) -0.13572(13) 0.0250(4) Uani 1 1 d . . . . .
H6D H 0.123112 -0.017288 -0.120245 0.030 Uiso 1 1 calc R U . . .
C7D C 0.2308(2) -0.24728(14) -0.32290(13) 0.0262(4) Uani 1 1 d . . . . .
N1D N 0.42238(19) -0.26027(11) -0.04284(11) 0.0245(3) Uani 1 1 d G . . . .
H1D1 H 0.469326 -0.221479 -0.017281 0.037 Uiso 1 1 d G U . . .
H1D2 H 0.499125 -0.305160 -0.072175 0.037 Uiso 1 1 d G U . . .
N2D N 0.2263(2) -0.33612(12) -0.32731(12) 0.0318(4) Uani 1 1 d . . . . .
H2D1 H 0.220020 -0.359988 -0.377521 0.038 Uiso 1 1 calc R U . . .
H2D2 H 0.229643 -0.370653 -0.279999 0.038 Uiso 1 1 calc R U . . .
N3D N 0.2258(2) -0.19518(13) -0.39444(12) 0.0336(4) Uani 1 1 d . . . . .
H3D1 H 0.219481 -0.219111 -0.444624 0.040 Uiso 1 1 calc R U . . .
H3D2 H 0.228725 -0.136777 -0.391608 0.040 Uiso 1 1 calc R U . . .
O1D O 0.26814(18) -0.09030(9) 0.00003(9) 0.0265(3) Uani 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
O1W H11W 0.8600 . ?
O1W H12W 0.8600 . ?
O2W H21W 0.8600 . ?
O2W H22W 0.8600 . ?
O3W H31W 0.8600 . ?
O3W H32W 0.8600 . ?
O4W H41W 0.8600 . ?
O4W H42W 0.8600 . ?
C1A O1A 1.328(2) . ?
C1A C6A 1.393(3) . ?
C1A C2A 1.421(2) . ?
C2A C3A 1.381(3) . ?
C2A N1A 1.407(2) . ?
C3A C4A 1.404(3) . ?
C3A H3A 0.9400 . ?
C4A C5A 1.395(3) . ?
C4A C7A 1.470(2) . ?
C5A C6A 1.385(3) . ?
C5A H5A 0.9400 . ?
C6A H6A 0.9400 . ?
C7A N2A 1.317(3) . ?
C7A N3A 1.320(3) . ?
N1A H1A1 0.9000 . ?
N1A H1A2 0.9001 . ?
N2A H2A1 0.8700 . ?
N2A H2A2 0.8700 . ?
N3A H3A1 0.8700 . ?
N3A H3A2 0.8700 . ?
O1A H1AB 1.231(10) . ?
C1B O1B 1.338(2) . ?
C1B C6B 1.396(3) . ?
C1B C2B 1.413(2) . ?
C2B C3B 1.381(3) . ?
C2B N1B 1.409(2) . ?
C3B C4B 1.394(3) . ?
C3B H3B 0.9400 . ?
C4B C5B 1.402(3) . ?
C4B C7B 1.469(2) . ?
C5B C6B 1.386(3) . ?
C5B H5B 0.9400 . ?
C6B H6B 0.9400 . ?
C7B N3B 1.312(3) . ?
C7B N2B 1.323(3) . ?
N1B H1B1 0.9000 . ?
N1B H1B2 0.9000 . ?
N2B H2B1 0.8700 . ?
N2B H2B2 0.8700 . ?
N3B H3B1 0.8700 . ?
N3B H3B2 0.8700 . ?
O1B H1AB 1.222(10) . ?
C1C O1C 1.339(2) . ?
C1C C6C 1.394(3) . ?
C1C C2C 1.412(2) . ?
C2C C3C 1.384(3) . ?
C2C N1C 1.411(2) . ?
C3C C4C 1.403(3) . ?
C3C H3C 0.9400 . ?
C4C C5C 1.397(3) . ?
C4C C7C 1.468(3) . ?
C5C C6C 1.384(3) . ?
C5C H5C 0.9400 . ?
C6C H6C 0.9400 . ?
C7C N3C 1.318(3) . ?
C7C N2C 1.323(3) . ?
N1C H1C1 0.9000 . ?
N1C H1C2 0.9000 . ?
N2C H2C1 0.8700 . ?
N2C H2C2 0.8700 . ?
N3C H3C1 0.8700 . ?
N3C H3C2 0.8700 . ?
O1C H1CD 1.227(10) . ?
C1D O1D 1.333(2) . ?
C1D C6D 1.402(3) . ?
C1D C2D 1.419(2) . ?
C2D C3D 1.381(3) . ?
C2D N1D 1.408(2) . ?
C3D C4D 1.407(3) . ?
C3D H3D 0.9400 . ?
C4D C5D 1.397(3) . ?
C4D C7D 1.469(3) . ?
C5D C6D 1.386(3) . ?
C5D H5D 0.9400 . ?
C6D H6D 0.9400 . ?
C7D N3D 1.315(3) . ?
C7D N2D 1.323(3) . ?
N1D H1D1 0.9000 . ?
N1D H1D2 0.9000 . ?
N2D H2D1 0.8700 . ?
N2D H2D2 0.8700 . ?
N3D H3D1 0.8700 . ?
N3D H3D2 0.8700 . ?
O1D H1CD 1.228(10) . ?

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
H11W O1W H12W 109.5 . . ?
H21W O2W H22W 109.5 . . ?
H31W O3W H32W 109.5 . . ?
H41W O4W H42W 109.5 . . ?
O1A C1A C6A 123.16(17) . . ?
O1A C1A C2A 118.25(16) . . ?
C6A C1A C2A 118.59(17) . . ?
C3A C2A N1A 123.06(16) . . ?
C3A C2A C1A 120.22(17) . . ?
N1A C2A C1A 116.70(16) . . ?
C2A C3A C4A 120.49(17) . . ?
C2A C3A H3A 119.8 . . ?
C4A C3A H3A 119.8 . . ?
C5A C4A C3A 119.26(17) . . ?
C5A C4A C7A 119.70(17) . . ?
C3A C4A C7A 121.04(17) . . ?
C6A C5A C4A 120.43(17) . . ?
C6A C5A H5A 119.8 . . ?
C4A C5A H5A 119.8 . . ?
C5A C6A C1A 120.99(17) . . ?
C5A C6A H6A 119.5 . . ?
C1A C6A H6A 119.5 . . ?
N2A C7A N3A 119.95(18) . . ?
N2A C7A C4A 120.82(18) . . ?
N3A C7A C4A 119.23(18) . . ?
C2A N1A H1A1 116.0 . . ?
C2A N1A H1A2 107.0 . . ?
H1A1 N1A H1A2 109.5 . . ?
C7A N2A H2A1 120.0 . . ?
C7A N2A H2A2 120.0 . . ?
H2A1 N2A H2A2 120.0 . . ?
C7A N3A H3A1 120.0 . . ?
C7A N3A H3A2 120.0 . . ?
H3A1 N3A H3A2 120.0 . . ?
C1A O1A H1AB 109.7(18) . . ?
O1B C1B C6B 122.93(17) . . ?
O1B C1B C2B 117.96(17) . . ?
C6B C1B C2B 119.11(17) . . ?
C3B C2B N1B 122.10(16) . . ?
C3B C2B C1B 119.88(17) . . ?
N1B C2B C1B 117.98(16) . . ?
C2B C3B C4B 120.81(17) . . ?
C2B C3B H3B 119.6 . . ?
C4B C3B H3B 119.6 . . ?
C3B C4B C5B 119.50(17) . . ?
C3B C4B C7B 120.39(17) . . ?
C5B C4B C7B 120.07(17) . . ?
C6B C5B C4B 119.98(18) . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C5B C6B C1B 120.70(17) . . ?
C5B C6B H6B 119.7 . . ?
C1B C6B H6B 119.7 . . ?
N3B C7B N2B 120.41(18) . . ?
N3B C7B C4B 119.36(18) . . ?
N2B C7B C4B 120.23(18) . . ?
C2B N1B H1B1 109.8 . . ?
C2B N1B H1B2 115.6 . . ?
H1B1 N1B H1B2 109.5 . . ?
C7B N2B H2B1 120.0 . . ?
C7B N2B H2B2 120.0 . . ?
H2B1 N2B H2B2 120.0 . . ?
C7B N3B H3B1 120.0 . . ?
C7B N3B H3B2 120.0 . . ?
H3B1 N3B H3B2 120.0 . . ?
C1B O1B H1AB 111.2(18) . . ?
O1C C1C C6C 123.30(17) . . ?
O1C C1C C2C 118.02(17) . . ?
C6C C1C C2C 118.68(17) . . ?
C3C C2C N1C 122.18(16) . . ?
C3C C2C C1C 120.23(17) . . ?
N1C C2C C1C 117.56(16) . . ?
C2C C3C C4C 120.52(16) . . ?
C2C C3C H3C 119.7 . . ?
C4C C3C H3C 119.7 . . ?
C5C C4C C3C 119.20(17) . . ?
C5C C4C C7C 120.28(17) . . ?
C3C C4C C7C 120.52(17) . . ?
C6C C5C C4C 120.27(17) . . ?
C6C C5C H5C 119.9 . . ?
C4C C5C H5C 119.9 . . ?
C5C C6C C1C 121.10(17) . . ?
C5C C6C H6C 119.4 . . ?
C1C C6C H6C 119.4 . . ?
N3C C7C N2C 120.15(18) . . ?
N3C C7C C4C 119.50(17) . . ?
N2C C7C C4C 120.36(17) . . ?
C2C N1C H1C1 111.3 . . ?
C2C N1C H1C2 108.9 . . ?
H1C1 N1C H1C2 109.5 . . ?
C7C N2C H2C1 120.0 . . ?
C7C N2C H2C2 120.0 . . ?
H2C1 N2C H2C2 120.0 . . ?
C7C N3C H3C1 120.0 . . ?
C7C N3C H3C2 120.0 . . ?
H3C1 N3C H3C2 120.0 . . ?
C1C O1C H1CD 109(2) . . ?
O1D C1D C6D 122.91(17) . . ?
O1D C1D C2D 118.13(17) . . ?
C6D C1D C2D 118.95(17) . . ?
C3D C2D N1D 123.13(17) . . ?
C3D C2D C1D 119.98(17) . . ?
N1D C2D C1D 116.86(16) . . ?
C2D C3D C4D 120.65(17) . . ?
C2D C3D H3D 119.7 . . ?
C4D C3D H3D 119.7 . . ?
C5D C4D C3D 119.31(17) . . ?
C5D C4D C7D 119.35(17) . . ?
C3D C4D C7D 121.33(17) . . ?
C6D C5D C4D 120.44(18) . . ?
C6D C5D H5D 119.8 . . ?
C4D C5D H5D 119.8 . . ?
C5D C6D C1D 120.61(17) . . ?
C5D C6D H6D 119.7 . . ?
C1D C6D H6D 119.7 . . ?
N3D C7D N2D 119.94(18) . . ?
N3D C7D C4D 119.39(18) . . ?
N2D C7D C4D 120.67(18) . . ?
C2D N1D H1D1 111.8 . . ?
C2D N1D H1D2 111.0 . . ?
H1D1 N1D H1D2 109.5 . . ?
C7D N2D H2D1 120.0 . . ?
C7D N2D H2D2 120.0 . . ?
H2D1 N2D H2D2 120.0 . . ?
C7D N3D H3D1 120.0 . . ?
C7D N3D H3D2 120.0 . . ?
H3D1 N3D H3D2 120.0 . . ?
C1D O1D H1CD 111(2) . . ?

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
O1A C1A C2A C3A -178.31(16) . . . . ?
C6A C1A C2A C3A 1.7(3) . . . . ?
O1A C1A C2A N1A -0.2(2) . . . . ?
C6A C1A C2A N1A 179.82(16) . . . . ?
N1A C2A C3A C4A 179.98(16) . . . . ?
C1A C2A C3A C4A -2.0(3) . . . . ?
C2A C3A C4A C5A 1.1(3) . . . . ?
C2A C3A C4A C7A -179.46(16) . . . . ?
C3A C4A C5A C6A 0.2(3) . . . . ?
C7A C4A C5A C6A -179.29(18) . . . . ?
C4A C5A C6A C1A -0.5(3) . . . . ?
O1A C1A C6A C5A 179.56(17) . . . . ?
C2A C1A C6A C5A -0.5(3) . . . . ?
C5A C4A C7A N2A 152.2(2) . . . . ?
C3A C4A C7A N2A -27.2(3) . . . . ?
C5A C4A C7A N3A -28.5(3) . . . . ?
C3A C4A C7A N3A 152.1(2) . . . . ?
O1B C1B C2B C3B 179.09(16) . . . . ?
C6B C1B C2B C3B -1.0(3) . . . . ?
O1B C1B C2B N1B 1.4(2) . . . . ?
C6B C1B C2B N1B -178.70(16) . . . . ?
N1B C2B C3B C4B 177.94(16) . . . . ?
C1B C2B C3B C4B 0.4(3) . . . . ?
C2B C3B C4B C5B 0.4(3) . . . . ?
C2B C3B C4B C7B -177.46(16) . . . . ?
C3B C4B C5B C6B -0.4(3) . . . . ?
C7B C4B C5B C6B 177.39(18) . . . . ?
C4B C5B C6B C1B -0.2(3) . . . . ?
O1B C1B C6B C5B -179.17(17) . . . . ?
C2B C1B C6B C5B 1.0(3) . . . . ?
C3B C4B C7B N3B -151.0(2) . . . . ?
C5B C4B C7B N3B 31.2(3) . . . . ?
C3B C4B C7B N2B 28.9(3) . . . . ?
C5B C4B C7B N2B -148.9(2) . . . . ?
O1C C1C C2C C3C -179.67(15) . . . . ?
C6C C1C C2C C3C 0.2(3) . . . . ?
O1C C1C C2C N1C -1.6(2) . . . . ?
C6C C1C C2C N1C 178.28(16) . . . . ?
N1C C2C C3C C4C -178.13(16) . . . . ?
C1C C2C C3C C4C -0.2(3) . . . . ?
C2C C3C C4C C5C 0.2(3) . . . . ?
C2C C3C C4C C7C 179.20(16) . . . . ?
C3C C4C C5C C6C -0.4(3) . . . . ?
C7C C4C C5C C6C -179.34(18) . . . . ?
C4C C5C C6C C1C 0.4(3) . . . . ?
O1C C1C C6C C5C 179.53(17) . . . . ?
C2C C1C C6C C5C -0.4(3) . . . . ?
C5C C4C C7C N3C -27.1(3) . . . . ?
C3C C4C C7C N3C 153.94(19) . . . . ?
C5C C4C C7C N2C 153.25(19) . . . . ?
C3C C4C C7C N2C -25.7(3) . . . . ?
O1D C1D C2D C3D 178.01(16) . . . . ?
C6D C1D C2D C3D -2.5(3) . . . . ?
O1D C1D C2D N1D -0.1(2) . . . . ?
C6D C1D C2D N1D 179.36(16) . . . . ?
N1D C2D C3D C4D -179.69(16) . . . . ?
C1D C2D C3D C4D 2.3(3) . . . . ?
C2D C3D C4D C5D -0.4(3) . . . . ?
C2D C3D C4D C7D 179.77(17) . . . . ?
C3D C4D C5D C6D -1.3(3) . . . . ?
C7D C4D C5D C6D 178.54(18) . . . . ?
C4D C5D C6D C1D 1.0(3) . . . . ?
O1D C1D C6D C5D -179.71(17) . . . . ?
C2D C1D C6D C5D 0.8(3) . . . . ?
C5D C4D C7D N3D 32.7(3) . . . . ?
C3D C4D C7D N3D -147.45(19) . . . . ?
C5D C4D C7D N2D -147.8(2) . . . . ?
C3D C4D C7D N2D 32.0(3) . . . . ?

_refine_diff_density_max         0.683
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.059

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_8e_295K
_database_code_depnum_ccdc_archive 'CCDC 2060892'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C11 H17 N3 O, 2(C H3 O3 S), H2 O'
_chemical_formula_sum            'C13 H25 N3 O8 S2'
_chemical_formula_weight         415.48

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3183(7)
_cell_length_b                   9.8382(7)
_cell_length_c                   11.2711(8)
_cell_angle_alpha                78.160(6)
_cell_angle_beta                 78.258(6)
_cell_angle_gamma                73.277(6)
_cell_volume                     956.96(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2851
_cell_measurement_theta_min      5.0260
_cell_measurement_theta_max      32.6130

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.751
_exptl_crystal_size_mid          0.550
_exptl_crystal_size_min          0.337
_exptl_absorpt_coefficient_mu    0.324
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.95428
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            6996
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.397
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3446
_reflns_number_gt                2964
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0559P)²+0.5302P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3446
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

# start Validation Reply Form
_vrf_PLAT910_8e_295K             
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         19 Note  
RESPONSE: Some low-angle reflections were obscured by the beamstop.
;
# end Validation Reply Form

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 0.4914(2) 0.7996(2) 1.08116(16) 0.0364(4) Uani 1 1 d . . . . .
H11N H 0.518908 0.742416 1.149333 0.063(9) Uiso 1 1 calc R . . . .
H21N H 0.430069 0.882594 1.099979 0.054(8) Uiso 1 1 calc R . . . .
H31N H 0.573485 0.815755 1.030430 0.069(9) Uiso 1 1 calc R . . . .
N2 N 0.3266(2) 0.8643(2) 0.65308(17) 0.0421(5) Uani 1 1 d . . . . .
H2N H 0.307525 0.928885 0.699276 0.055(8) Uiso 1 1 calc R . . . .
N3 N 0.3434(2) 0.6269(2) 0.64745(17) 0.0441(5) Uani 1 1 d . . . . .
H3N H 0.369766 0.541212 0.686782 0.052(8) Uiso 1 1 calc R . . . .
O1 O 0.3516(2) 0.59931(19) 1.21445(14) 0.0455(4) Uani 1 1 d . . . . .
H1O H 0.316655 0.530692 1.246844 0.072(10) Uiso 1 1 calc R . . . .
C1 C 0.3431(2) 0.6264(2) 1.09366(18) 0.0332(5) Uani 1 1 d . . . . .
C2 C 0.4122(2) 0.7304(2) 1.02162(19) 0.0314(4) Uani 1 1 d . . . . .
C3 C 0.4108(2) 0.7652(2) 0.89736(19) 0.0331(5) Uani 1 1 d . . . . .
H3 H 0.457950 0.834623 0.851101 0.040 Uiso 1 1 calc R U . . .
C4 C 0.3383(2) 0.6957(2) 0.84090(19) 0.0334(5) Uani 1 1 d . . . . .
C5 C 0.2685(3) 0.5923(2) 0.9131(2) 0.0365(5) Uani 1 1 d . . . . .
H5 H 0.219651 0.545537 0.876403 0.044 Uiso 1 1 calc R U . . .
C6 C 0.2703(2) 0.5579(2) 1.0373(2) 0.0363(5) Uani 1 1 d . . . . .
H6 H 0.222823 0.488845 1.083768 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3362(2) 0.7311(2) 0.7071(2) 0.0355(5) Uani 1 1 d . . . . .
C8 C 0.3459(4) 0.9112(3) 0.5205(2) 0.0601(8) Uani 1 1 d . . . . .
H8A H 0.440518 0.852341 0.483663 0.072 Uiso 1 1 calc R U . . .
H8B H 0.354068 1.009665 0.504056 0.072 Uiso 1 1 calc R U . . .
C9 C 0.2219(5) 0.9035(4) 0.4606(3) 0.0805(10) Uani 1 1 d . . . . .
H9A H 0.250767 0.923662 0.372413 0.097 Uiso 1 1 calc R U . . .
H9B H 0.132194 0.978083 0.483622 0.097 Uiso 1 1 calc R U . . .
C10 C 0.1819(4) 0.7613(4) 0.4921(3) 0.0706(9) Uani 1 1 d . . . . .
H10A H 0.100574 0.765116 0.561495 0.085 Uiso 1 1 calc R U . . .
H10B H 0.144546 0.745521 0.423128 0.085 Uiso 1 1 calc R U . . .
C11 C 0.3126(4) 0.6372(3) 0.5230(2) 0.0579(7) Uani 1 1 d . . . . .
H11A H 0.290942 0.548894 0.515456 0.070 Uiso 1 1 calc R U . . .
H11B H 0.402380 0.647575 0.464601 0.070 Uiso 1 1 calc R U . . .
S1 S 0.74531(7) 0.74927(6) 0.29770(5) 0.03722(17) Uani 1 1 d . . . . .
O2 O 0.6468(2) 0.66837(18) 0.27669(16) 0.0495(4) Uani 1 1 d . . . . .
O3 O 0.7429(3) 0.7464(2) 0.42584(16) 0.0714(6) Uani 1 1 d . . . . .
O4 O 0.7145(2) 0.89314(18) 0.22908(16) 0.0558(5) Uani 1 1 d . . . . .
C12 C 0.9292(3) 0.6602(4) 0.2387(3) 0.0707(9) Uani 1 1 d . . . . .
H12A H 0.999891 0.708487 0.250765 0.106 Uiso 1 1 calc R U . . .
H12B H 0.935515 0.660350 0.152579 0.106 Uiso 1 1 calc R U . . .
H12C H 0.953031 0.562917 0.280316 0.106 Uiso 1 1 calc R U . . .
S2 S 0.82618(7) 0.84097(7) 0.86261(5) 0.04376(19) Uani 1 1 d . . . . .
O5 O 0.8913(2) 0.7798(2) 0.75336(18) 0.0706(6) Uani 1 1 d . . . . .
O6 O 0.8163(4) 0.7336(3) 0.9688(2) 0.0945(8) Uani 1 1 d . . . . .
O7 O 0.6793(2) 0.9386(2) 0.8565(3) 0.0813(7) Uani 1 1 d . . . . .
C13 C 0.9420(4) 0.9418(4) 0.8824(4) 0.0881(12) Uani 1 1 d . . . . .
H13A H 1.041299 0.880396 0.891061 0.132 Uiso 1 1 calc R U . . .
H13B H 0.899862 0.985567 0.954734 0.132 Uiso 1 1 calc R U . . .
H13C H 0.948949 1.015138 0.812288 0.132 Uiso 1 1 calc R U . . .
O1W O 0.7431(4) 0.6214(3) 0.6665(2) 0.0893(9) Uani 1 1 d G . . . .
H11W H 0.734711 0.658029 0.595369 0.087(12) Uiso 1 1 d G . . . .
H12W H 0.786986 0.668106 0.691975 0.089(12) Uiso 1 1 d G . . . .


_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 C2 1.461(3) . ?
N1 H11N 0.8900 . ?
N1 H21N 0.8900 . ?
N1 H31N 0.8900 . ?
N2 C7 1.313(3) . ?
N2 C8 1.461(3) . ?
N2 H2N 0.8600 . ?
N3 C7 1.316(3) . ?
N3 C11 1.466(3) . ?
N3 H3N 0.8600 . ?
O1 C1 1.347(2) . ?
O1 H1O 0.8200 . ?
C1 C6 1.390(3) . ?
C1 C2 1.395(3) . ?
C2 C3 1.374(3) . ?
C3 C4 1.396(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(3) . ?
C4 C7 1.479(3) . ?
C5 C6 1.373(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.478(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.505(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.496(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
S1 O3 1.4345(18) . ?
S1 O4 1.4462(17) . ?
S1 O2 1.4554(17) . ?
S1 C12 1.748(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
S2 O5 1.4271(19) . ?
S2 O6 1.431(2) . ?
S2 O7 1.434(2) . ?
S2 C13 1.732(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O1W H11W 0.8178 . ?
O1W H12W 0.8196 . ?

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
C2 N1 H11N 109.5 . . ?
C2 N1 H21N 109.5 . . ?
H11N N1 H21N 109.5 . . ?
C2 N1 H31N 109.5 . . ?
H11N N1 H31N 109.5 . . ?
H21N N1 H31N 109.5 . . ?
C7 N2 C8 125.0(2) . . ?
C7 N2 H2N 117.5 . . ?
C8 N2 H2N 117.5 . . ?
C7 N3 C11 128.8(2) . . ?
C7 N3 H3N 115.6 . . ?
C11 N3 H3N 115.6 . . ?
C1 O1 H1O 109.5 . . ?
O1 C1 C6 124.24(19) . . ?
O1 C1 C2 117.19(19) . . ?
C6 C1 C2 118.57(19) . . ?
C3 C2 C1 121.7(2) . . ?
C3 C2 N1 120.12(19) . . ?
C1 C2 N1 118.18(18) . . ?
C2 C3 C4 119.65(19) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 118.65(19) . . ?
C5 C4 C7 120.9(2) . . ?
C3 C4 C7 120.48(19) . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N2 C7 N3 122.8(2) . . ?
N2 C7 C4 119.0(2) . . ?
N3 C7 C4 118.20(19) . . ?
N2 C8 C9 114.5(3) . . ?
N2 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
N2 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 C10 114.6(2) . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 113.3(3) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N3 C11 C10 112.4(2) . . ?
N3 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
N3 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
O3 S1 O4 113.11(12) . . ?
O3 S1 O2 112.23(12) . . ?
O4 S1 O2 111.51(11) . . ?
O3 S1 C12 106.96(15) . . ?
O4 S1 C12 106.84(15) . . ?
O2 S1 C12 105.63(15) . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 S2 O6 112.22(15) . . ?
O5 S2 O7 113.59(14) . . ?
O6 S2 O7 108.82(18) . . ?
O5 S2 C13 107.68(17) . . ?
O6 S2 C13 108.34(19) . . ?
O7 S2 C13 105.88(15) . . ?
S2 C13 H13A 109.5 . . ?
S2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H11W O1W H12W 106.5 . . ?

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 C1 C2 C3 179.53(19) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
O1 C1 C2 N1 1.5(3) . . . . ?
C6 C1 C2 N1 -178.65(19) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
N1 C2 C3 C4 178.29(19) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 C3 C4 C7 -179.70(19) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C7 C4 C5 C6 179.7(2) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
O1 C1 C6 C5 -179.6(2) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C8 N2 C7 N3 -9.9(4) . . . . ?
C8 N2 C7 C4 170.4(2) . . . . ?
C11 N3 C7 N2 -13.5(4) . . . . ?
C11 N3 C7 C4 166.2(2) . . . . ?
C5 C4 C7 N2 144.8(2) . . . . ?
C3 C4 C7 N2 -35.4(3) . . . . ?
C5 C4 C7 N3 -35.0(3) . . . . ?
C3 C4 C7 N3 144.8(2) . . . . ?
C7 N2 C8 C9 69.9(4) . . . . ?
N2 C8 C9 C10 -50.6(4) . . . . ?
C8 C9 C10 C11 -28.7(4) . . . . ?
C7 N3 C11 C10 -38.0(4) . . . . ?
C9 C10 C11 N3 77.7(3) . . . . ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.046

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_8g_295K
_database_code_depnum_ccdc_archive 'CCDC 2060893'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;

_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C7 H11 N3 O, 2(Cl)'
_chemical_formula_sum            'C7 H11 Cl2 N3 O'
_chemical_formula_weight         224.09

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'
Cl Cl 0.1484 0.1585 '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                   4.4199(3)
_cell_length_b                   11.7058(6)
_cell_length_c                   20.2357(15)
_cell_angle_alpha                90.0
_cell_angle_beta                 93.014(6)
_cell_angle_gamma                90.0
_cell_volume                     1045.51(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1621
_cell_measurement_theta_min      4.6040
_cell_measurement_theta_max      31.1540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.614
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.094
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            1892
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         4.394
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measurement_method       'ω scans'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1596
_reflns_number_total             1892
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2017)'
_computing_structure_solution    'SIR-2014 (Burla et al., 2015)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1892
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.066
_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)+(0.0499P)²+0.0144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0966
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8831(15)
 0.1169(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6)
3.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N3(H3A,H3B)
3.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;

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 0.5821(4) 0.02966(14) 0.72518(9) 0.0423(5) Uani 1 1 d . . . . .
H1 H 0.517906 -0.004241 0.691861 0.051(9) Uiso 1 1 calc R . . . .
N1 N 0.7691(5) 0.17113(17) 0.82402(10) 0.0365(5) Uani 1 1 d . . . . .
H1A H 0.914710 0.133380 0.846877 0.053(8) Uiso 1 1 calc R . . . .
H1B H 0.599705 0.129874 0.822441 0.067(10) Uiso 1 1 calc R . . . .
H1C H 0.736035 0.237650 0.843684 0.067(10) Uiso 1 1 calc R . . . .
N2 N 1.2375(5) 0.15124(18) 0.52938(11) 0.0446(6) Uani 1 1 d . . . . .
H2A H 1.295445 0.159862 0.489780 0.080(11) Uiso 1 1 calc R . . . .
H2B H 1.237661 0.084401 0.547032 0.045(8) Uiso 1 1 calc R . . . .
N3 N 1.1450(6) 0.34294(19) 0.53796(12) 0.0539(6) Uani 1 1 d . . . . .
H3A H 1.201811 0.353944 0.498461 0.066(10) Uiso 1 1 calc R . . . .
H3B H 1.085781 0.399676 0.560989 0.091(13) Uiso 1 1 calc R . . . .
C1 C 0.8622(5) 0.19157(19) 0.75693(11) 0.0304(5) Uani 1 1 d . . . . .
C2 C 0.7689(5) 0.11577(18) 0.70773(12) 0.0300(5) Uani 1 1 d . . . . .
C3 C 0.8669(5) 0.13112(19) 0.64479(12) 0.0321(5) Uani 1 1 d . . . . .
H3 H 0.810907 0.079421 0.611456 0.034(6) Uiso 1 1 calc R . . . .
C4 C 1.0494(5) 0.22385(18) 0.63122(11) 0.0310(5) Uani 1 1 d . . . . .
C5 C 1.1406(5) 0.3007(2) 0.68069(12) 0.0374(6) Uani 1 1 d . . . . .
H5 H 1.263488 0.362559 0.671534 0.045 Uiso 1 1 calc R U . . .
C6 C 1.0445(5) 0.2830(2) 0.74400(12) 0.0369(6) Uani 1 1 d . . . . .
H6 H 1.103677 0.333240 0.777849 0.044 Uiso 1 1 calc R U . . .
C7 C 1.1486(5) 0.2402(2) 0.56293(12) 0.0350(6) Uani 1 1 d . . . . .
Cl1 Cl 0.36423(14) 0.89725(5) 0.60053(3) 0.0434(2) Uani 1 1 d . . . . .
Cl2 Cl 0.72141(14) 0.54104(5) 0.60147(3) 0.0435(2) 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 0.8200 . ?
O1 C2 1.361(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.459(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C7 1.314(3) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C7 1.304(3) . ?
C1 C2 1.380(3) . ?
C1 C6 1.373(3) . ?
C2 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(3) . ?
C4 C5 1.389(3) . ?
C4 C7 1.484(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(3) . ?
C6 H6 0.9300 . ?

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
C2 O1 H1 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H2A N2 H2B 120.0 . . ?
C7 N2 H2A 120.0 . . ?
C7 N2 H2B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C7 N3 H3A 120.0 . . ?
C7 N3 H3B 120.0 . . ?
C2 C1 N1 118.5(2) . . ?
C6 C1 N1 120.1(2) . . ?
C6 C1 C2 121.3(2) . . ?
O1 C2 C1 116.8(2) . . ?
O1 C2 C3 124.1(2) . . ?
C3 C2 C1 119.1(2) . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 C7 119.2(2) . . ?
C5 C4 C7 119.9(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N2 C7 C4 119.3(2) . . ?
N3 C7 N2 121.9(2) . . ?
N3 C7 C4 118.8(2) . . ?

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 C2 C3 C4 177.8(2) . . . . ?
N1 C1 C2 O1 3.2(3) . . . . ?
N1 C1 C2 C3 -177.00(19) . . . . ?
N1 C1 C6 C5 178.1(2) . . . . ?
C1 C2 C3 C4 -1.9(3) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C2 C3 C4 C7 -179.0(2) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C3 C4 C7 N2 -42.2(3) . . . . ?
C3 C4 C7 N3 137.8(2) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C5 C4 C7 N2 137.5(2) . . . . ?
C5 C4 C7 N3 -42.5(3) . . . . ?
C6 C1 C2 O1 -178.3(2) . . . . ?
C6 C1 C2 C3 1.5(3) . . . . ?
C7 C4 C5 C6 -179.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8831(15)
2 0.1169(15)
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_8h_170K
_database_code_depnum_ccdc_archive 'CCDC 2060894'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C9 H12 N3 O, Cl, 2(H2 O)'
_chemical_formula_sum            'C9 H16 Cl N3 O3'
_chemical_formula_weight         249.70

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7656(2)
_cell_length_b                   9.4132(2)
_cell_length_c                   10.2539(2)
_cell_angle_alpha                108.3092(11)
_cell_angle_beta                 96.7180(11)
_cell_angle_gamma                102.1891(10)
_cell_volume                     594.05(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    170.0(1)
_cell_measurement_reflns_used    2551
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.485

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.319
_shelx_estimated_absorpt_T_min   0.880
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6589
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS 2008 (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      170.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD with APEXII detector'
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ scans + ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            11385
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.572
_diffrn_reflns_theta_max         27.377
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2641
_reflns_number_gt                2227
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+0.2537P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2641
_refine_ls_number_parameters     160
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

# start Validation Reply Form
_vrf_PLAT417_8h_170K             
;
PROBLEM: Short Inter D-H..H-D       H2WA     ..H1'              2.09 Ang.  
PROBLEM: Short Inter D-H..H-D       H11W     ..H1'              2.11 Ang.  
RESPONSE: The two hydrogen atoms are bound to two hydrogen-bonded oxygen atoms.
 H1' belongs to a minor (ca. 5 %) disorder component.
;
# end Validation Reply Form

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 1.10452(7) 0.16387(5) 0.84797(4) 0.04507(15) Uani 1 1 d . . . . .
O1W O 0.7185(2) 0.17096(17) 0.64754(15) 0.0536(4) Uani 1 1 d G . . . .
H11W H 0.825762 0.163593 0.698147 0.080 Uiso 1 1 d G U . . .
H12W H 0.716148 0.123880 0.559321 0.080 Uiso 1 1 d G U . . .
O2W O 0.3549(2) -0.03969(16) 0.65441(16) 0.0556(4) Uani 1 1 d G . . . .
H2WA H 0.274529 0.011204 0.697903 0.083 Uiso 1 1 d G U . . .
H2WB H 0.472437 0.024512 0.661916 0.083 Uiso 1 1 d G U . . .
C1 C 0.8055(3) 0.7093(2) 0.67443(17) 0.0376(4) Uani 1 1 d D . . . .
C2 C 0.7705(3) 0.54737(19) 0.63446(17) 0.0360(4) Uani 1 1 d D . . . .
H2' H 0.767396 0.500683 0.704230 0.043 Uiso 0.052(3) 1 calc R U P A 2
O1 O 0.7706(2) 0.49067(16) 0.74231(13) 0.0488(4) Uani 0.948(3) 1 d D . P A 1
H1 H 0.747805 0.393691 0.709897 0.073 Uiso 0.948(3) 1 calc R U P A 1
C3 C 0.7407(3) 0.45599(19) 0.49655(17) 0.0356(4) Uani 1 1 d D . . . .
H3 H 0.717790 0.346927 0.471956 0.043 Uiso 1 1 calc R U . . .
C4 C 0.7437(2) 0.52151(18) 0.39145(17) 0.0341(3) Uani 1 1 d D . . . .
C5 C 0.7757(3) 0.6814(2) 0.42976(18) 0.0412(4) Uani 1 1 d D . . . .
H5 H 0.776017 0.727539 0.359618 0.049 Uiso 1 1 calc R U . . .
C6 C 0.8070(3) 0.7730(2) 0.56834(19) 0.0446(4) Uani 1 1 d D . . . .
H6 H 0.830047 0.882072 0.592516 0.053 Uiso 0.948(3) 1 calc R U P A 1
O1' O 0.855(4) 0.9304(10) 0.6019(19) 0.0488(4) Uani 0.052(3) 1 d D . P A 2
H1' H 0.953914 0.972271 0.670751 0.073 Uiso 0.052(3) 1 calc DR U P A 2
C7 C 0.7148(2) 0.42521(19) 0.24567(17) 0.0345(3) Uani 1 1 d . . . . .
C8 C 0.6443(3) 0.2088(2) 0.04589(19) 0.0474(4) Uani 1 1 d . . . . .
H8A H 0.497511 0.153276 0.005236 0.057 Uiso 1 1 calc R U . . .
H8B H 0.731214 0.137396 0.013635 0.057 Uiso 1 1 calc R U . . .
C9 C 0.7070(3) 0.3545(2) 0.00822(19) 0.0497(5) Uani 1 1 d . . . . .
H9A H 0.841740 0.363676 -0.021515 0.060 Uiso 1 1 calc R U . . .
H9B H 0.601751 0.355055 -0.067186 0.060 Uiso 1 1 calc R U . . .
N1 N 0.8313(3) 0.79922(19) 0.81175(16) 0.0507(4) Uani 1 1 d G . . . .
H1A H 0.893992 0.902702 0.844682 0.076 Uiso 1 1 d DG U . . .
H1B H 0.845004 0.761075 0.882642 0.076 Uiso 1 1 d DG U . . .
N2 N 0.6802(2) 0.27297(17) 0.19863(15) 0.0420(3) Uani 1 1 d . . . . .
H2A H 0.678941 0.216709 0.252888 0.050 Uiso 1 1 calc R U . . .
N3 N 0.7197(3) 0.47799(17) 0.14007(15) 0.0434(4) Uani 1 1 d . . . . .
H3A H 0.729387 0.575296 0.148471 0.052 Uiso 1 1 calc 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
O1W H11W 0.8699 . ?
O1W H12W 0.8699 . ?
O2W H2WA 0.8699 . ?
O2W H2WB 0.8699 . ?
C1 N1 1.364(2) . ?
C1 C6 1.398(2) . ?
C1 C2 1.407(2) . ?
C2 C3 1.370(2) . ?
C2 O1 1.371(2) . ?
C2 H2' 0.9500 . ?
O1 H1 0.8400 . ?
C3 C4 1.400(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(2) . ?
C4 C7 1.449(2) . ?
C5 C6 1.375(2) . ?
C5 H5 0.9500 . ?
C6 O1' 1.367(8) . ?
C6 H6 0.9500 . ?
O1' H1' 0.8400 . ?
C7 N2 1.319(2) . ?
C7 N3 1.327(2) . ?
C8 N2 1.460(2) . ?
C8 C9 1.528(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N3 1.460(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?

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
H11W O1W H12W 109.5 . . ?
H2WA O2W H2WB 109.5 . . ?
N1 C1 C6 121.66(16) . . ?
N1 C1 C2 120.70(15) . . ?
C6 C1 C2 117.62(15) . . ?
C3 C2 O1 123.62(15) . . ?
C3 C2 C1 121.05(15) . . ?
O1 C2 C1 115.33(15) . . ?
C3 C2 H2' 119.5 . . ?
C1 C2 H2' 119.5 . . ?
C2 O1 H1 109.5 . . ?
C2 C3 C4 120.73(15) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.66(15) . . ?
C5 C4 C7 120.54(15) . . ?
C3 C4 C7 120.80(15) . . ?
C6 C5 C4 120.52(16) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
O1' C6 C5 118.4(8) . . ?
O1' C6 C1 120.0(8) . . ?
C5 C6 C1 121.42(16) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C6 O1' H1' 109.5 . . ?
N2 C7 N3 110.16(15) . . ?
N2 C7 C4 125.13(15) . . ?
N3 C7 C4 124.71(15) . . ?
N2 C8 C9 102.07(14) . . ?
N2 C8 H8A 111.4 . . ?
C9 C8 H8A 111.4 . . ?
N2 C8 H8B 111.4 . . ?
C9 C8 H8B 111.4 . . ?
H8A C8 H8B 109.2 . . ?
N3 C9 C8 102.30(14) . . ?
N3 C9 H9A 111.3 . . ?
C8 C9 H9A 111.3 . . ?
N3 C9 H9B 111.3 . . ?
C8 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C1 N1 H1A 122.4 . . ?
C1 N1 H1B 122.5 . . ?
H1A N1 H1B 109.5 . . ?
C7 N2 C8 112.00(14) . . ?
C7 N2 H2A 124.0 . . ?
C8 N2 H2A 124.0 . . ?
C7 N3 C9 111.53(14) . . ?
C7 N3 H3A 124.2 . . ?
C9 N3 H3A 124.2 . . ?

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 C1 C2 C3 178.83(16) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
N1 C1 C2 O1 -1.7(2) . . . . ?
C6 C1 C2 O1 179.97(16) . . . . ?
O1 C2 C3 C4 -179.60(16) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C4 C7 179.23(15) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C7 C4 C5 C6 -178.79(17) . . . . ?
C4 C5 C6 O1' 174.6(13) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
N1 C1 C6 O1' 6.5(14) . . . . ?
C2 C1 C6 O1' -175.3(13) . . . . ?
N1 C1 C6 C5 -178.36(18) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C5 C4 C7 N2 -178.85(17) . . . . ?
C3 C4 C7 N2 1.4(3) . . . . ?
C5 C4 C7 N3 1.3(3) . . . . ?
C3 C4 C7 N3 -178.51(16) . . . . ?
N2 C8 C9 N3 -13.20(19) . . . . ?
N3 C7 N2 C8 -3.9(2) . . . . ?
C4 C7 N2 C8 176.23(16) . . . . ?
C9 C8 N2 C7 11.2(2) . . . . ?
N2 C7 N3 C9 -5.9(2) . . . . ?
C4 C7 N3 C9 174.00(16) . . . . ?
C8 C9 N3 C7 12.3(2) . . . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.042


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# 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_8c'_295K
_database_code_depnum_ccdc_archive 'CCDC 2060890'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C10 H13 N3 O, H2 O'
_chemical_formula_sum            'C10 H15 N3 O2'
_chemical_formula_weight         209.25

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.5770(2)
_cell_length_b                   10.7154(3)
_cell_length_c                   15.0191(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1058.47(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3704
_cell_measurement_theta_min      4.6680
_cell_measurement_theta_max      32.1890

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.738
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.181
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.88250
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            9382
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.494
_diffrn_reflns_theta_max         25.224
_diffrn_reflns_theta_full        25.224
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1899
_reflns_number_gt                1812
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0658P)²+0.2695P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 696 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)
_chemical_absolute_configuration .
_refine_ls_number_reflns         1899
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1072
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 1.0661(3) 0.6850(2) 0.52485(14) 0.0327(5) Uani 1 1 d G . . . .
H11N H 0.970553 0.695774 0.566097 0.049 Uiso 1 1 d G U . . .
H12N H 1.127966 0.757445 0.514363 0.049 Uiso 1 1 d G U . . .
N2 N 0.4920(4) 0.3924(2) 0.43106(16) 0.0385(6) Uani 1 1 d . . . . .
H2N H 0.513092 0.443607 0.474144 0.044(9) Uiso 1 1 calc R . . . .
N3 N 0.5898(4) 0.3190(2) 0.29448(17) 0.0424(6) Uani 1 1 d . . . . .
H3N H 0.679576 0.316629 0.252868 0.053(10) Uiso 1 1 calc R . . . .
O1 O 1.2098(3) 0.76811(17) 0.36201(12) 0.0337(5) Uani 1 1 d . . . . .
C1 C 1.0927(4) 0.6698(2) 0.36324(17) 0.0278(5) Uani 1 1 d . . . . .
C2 C 1.0012(4) 0.6295(2) 0.44485(16) 0.0269(5) Uani 1 1 d . . . . .
C3 C 0.8543(4) 0.5385(2) 0.44423(17) 0.0277(5) Uani 1 1 d . . . . .
H3 H 0.792246 0.516004 0.497506 0.033 Uiso 1 1 calc R U . . .
C4 C 0.7954(4) 0.4783(2) 0.36511(17) 0.0270(5) Uani 1 1 d . . . . .
C5 C 0.8992(4) 0.5079(2) 0.28737(17) 0.0329(6) Uani 1 1 d . . . . .
H5 H 0.869280 0.465309 0.235016 0.040 Uiso 1 1 calc R U . . .
C6 C 1.0459(4) 0.5996(3) 0.28703(17) 0.0346(6) Uani 1 1 d . . . . .
H6 H 1.116386 0.615504 0.234560 0.041 Uiso 1 1 calc R U . . .
C7 C 0.6206(4) 0.3932(2) 0.36343(18) 0.0303(6) Uani 1 1 d . . . . .
C8 C 0.3169(5) 0.3098(3) 0.4369(2) 0.0510(8) Uani 1 1 d . . . . .
H8A H 0.194216 0.356445 0.423575 0.061 Uiso 1 1 calc R U . . .
H8B H 0.305462 0.277679 0.497027 0.061 Uiso 1 1 calc R U . . .
C9 C 0.3363(7) 0.2044(4) 0.3737(2) 0.0736(13) Uani 1 1 d . . . . .
H9A H 0.429069 0.143221 0.398526 0.088 Uiso 1 1 calc R U . . .
H9B H 0.204666 0.164671 0.367086 0.088 Uiso 1 1 calc R U . . .
C10 C 0.4094(6) 0.2412(4) 0.2865(2) 0.0597(10) Uani 1 1 d . . . . .
H10A H 0.303724 0.287036 0.255456 0.072 Uiso 1 1 calc R U . . .
H10B H 0.441419 0.167415 0.251845 0.072 Uiso 1 1 calc R U . . .
O1W O 0.4238(4) 0.54556(19) 0.57966(14) 0.0438(5) Uani 1 1 d G . . . .
H11W H 0.497799 0.601796 0.598674 0.050(10) Uiso 1 1 d G . . . .
H12W H 0.318745 0.583414 0.566635 0.056(11) Uiso 1 1 d G . . . .


_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 C2 1.407(3) . ?
N1 H11N 0.8900 . ?
N1 H12N 0.8900 . ?
N2 C7 1.322(3) . ?
N2 C8 1.455(4) . ?
N2 H2N 0.8600 . ?
N3 C7 1.321(3) . ?
N3 C10 1.455(4) . ?
N3 H3N 0.8600 . ?
O1 C1 1.305(3) . ?
C1 C6 1.404(4) . ?
C1 C2 1.432(3) . ?
C2 C3 1.373(4) . ?
C3 C4 1.406(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(4) . ?
C4 C7 1.468(3) . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.481(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.450(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
O1W H11W 0.8254 . ?
O1W H12W 0.8250 . ?

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
C2 N1 H11N 115.8 . . ?
C2 N1 H12N 110.8 . . ?
H11N N1 H12N 109.5 . . ?
C7 N2 C8 123.8(2) . . ?
C7 N2 H2N 118.1 . . ?
C8 N2 H2N 118.1 . . ?
C7 N3 C10 122.3(2) . . ?
C7 N3 H3N 118.9 . . ?
C10 N3 H3N 118.9 . . ?
O1 C1 C6 123.4(2) . . ?
O1 C1 C2 120.2(2) . . ?
C6 C1 C2 116.4(2) . . ?
C3 C2 N1 121.3(2) . . ?
C3 C2 C1 120.3(2) . . ?
N1 C2 C1 118.4(2) . . ?
C2 C3 C4 121.7(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 118.0(2) . . ?
C5 C4 C7 120.8(2) . . ?
C3 C4 C7 121.0(2) . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 122.2(2) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
N3 C7 N2 120.0(2) . . ?
N3 C7 C4 120.5(2) . . ?
N2 C7 C4 119.5(2) . . ?
N2 C8 C9 110.9(3) . . ?
N2 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 113.6(3) . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 N3 110.6(3) . . ?
C9 C10 H10A 109.5 . . ?
N3 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
H11W O1W H12W 102.5 . . ?

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 C1 C2 C3 170.0(2) . . . . ?
C6 C1 C2 C3 -8.9(3) . . . . ?
O1 C1 C2 N1 -10.3(3) . . . . ?
C6 C1 C2 N1 170.8(2) . . . . ?
N1 C2 C3 C4 -176.9(2) . . . . ?
C1 C2 C3 C4 2.8(4) . . . . ?
C2 C3 C4 C5 4.0(4) . . . . ?
C2 C3 C4 C7 -172.0(2) . . . . ?
C3 C4 C5 C6 -4.3(4) . . . . ?
C7 C4 C5 C6 171.7(2) . . . . ?
C4 C5 C6 C1 -2.2(4) . . . . ?
O1 C1 C6 C5 -170.2(2) . . . . ?
C2 C1 C6 C5 8.7(4) . . . . ?
C10 N3 C7 N2 4.6(4) . . . . ?
C10 N3 C7 C4 -174.5(3) . . . . ?
C8 N2 C7 N3 2.4(4) . . . . ?
C8 N2 C7 C4 -178.6(3) . . . . ?
C5 C4 C7 N3 17.4(4) . . . . ?
C3 C4 C7 N3 -166.8(2) . . . . ?
C5 C4 C7 N2 -161.7(3) . . . . ?
C3 C4 C7 N2 14.2(4) . . . . ?
C7 N2 C8 C9 17.2(5) . . . . ?
N2 C8 C9 C10 -43.1(5) . . . . ?
C8 C9 C10 N3 49.3(5) . . . . ?
C7 N3 C10 C9 -30.6(5) . . . . ?

_refine_diff_density_max         0.415
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.051

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# 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_8a'_170K
_database_code_depnum_ccdc_archive 'CCDC 2060887'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C7 H9 N3 O, 2(H2 O)'
_chemical_formula_sum            'C7 H13 N3 O3'
_chemical_formula_weight         187.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.1400(8)
_cell_length_b                   4.0229(4)
_cell_length_c                   10.8744(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.890(7)
_cell_angle_gamma                90
_cell_volume                     438.26(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    170.0(1)
_cell_measurement_reflns_used    1002
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.485

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4354
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS 2008 (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      170.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD with APEXII detector'
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ scans + ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            2959
_diffrn_reflns_av_unetI/netI     0.0981
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.895
_diffrn_reflns_theta_max         28.025
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_point_group_measured_fraction_full 0.946
_reflns_number_total             1918
_reflns_number_gt                1340
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.639
_reflns_Friedel_fraction_max     0.819
_reflns_Friedel_fraction_full    0.895

_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.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0841P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 
;
 Flack x determined using 424 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1918
_refine_ls_number_parameters     127
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1688
_refine_ls_wR_factor_gt          0.1466
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.6324(4) 0.5904(11) 0.2432(4) 0.0269(9) Uani 1 1 d . . . . .
C2 C 0.5898(4) 0.4020(11) 0.3408(4) 0.0282(10) Uani 1 1 d . . . . .
C3 C 0.4571(3) 0.3239(13) 0.3373(4) 0.0285(9) Uani 1 1 d . . . . .
H3 H 0.430686 0.197957 0.403313 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3600(4) 0.4265(11) 0.2384(4) 0.0272(10) Uani 1 1 d . . . . .
C5 C 0.4007(4) 0.6196(13) 0.1443(4) 0.0290(9) Uani 1 1 d . . . . .
H5 H 0.336393 0.698066 0.077781 0.035 Uiso 1 1 calc R U . . .
C6 C 0.5348(4) 0.6975(12) 0.1474(4) 0.0316(11) Uani 1 1 d . . . . .
H6 H 0.560367 0.827767 0.082102 0.038 Uiso 1 1 calc R U . . .
C7 C 0.2207(4) 0.3196(12) 0.2309(4) 0.0277(9) Uani 1 1 d . . . . .
N1 N 0.6877(3) 0.3039(11) 0.4416(4) 0.0335(9) Uani 1 1 d G . . . .
H1A H 0.664883 0.113710 0.478383 0.050 Uiso 1 1 d G U . . .
H1B H 0.762277 0.267485 0.406498 0.050 Uiso 1 1 d G U . . .
N2 N 0.1823(3) 0.1534(12) 0.3244(3) 0.0363(9) Uani 1 1 d . . . . .
H2A H 0.098781 0.088354 0.319720 0.044 Uiso 1 1 calc R U . . .
H2B H 0.240238 0.108019 0.391193 0.044 Uiso 1 1 calc R U . . .
N3 N 0.1321(3) 0.3840(11) 0.1322(4) 0.0361(10) Uani 1 1 d . . . . .
H3A H 0.049001 0.316986 0.129163 0.043 Uiso 1 1 calc R U . . .
H3B H 0.155773 0.494062 0.069189 0.043 Uiso 1 1 calc R U . . .
O1 O 0.7612(2) 0.6472(9) 0.2438(3) 0.0322(8) Uani 1 1 d . . . . .
O1W O 0.8591(3) 0.1487(10) 0.1162(3) 0.0344(8) Uani 1 1 d G . . . .
H11W H 0.830374 -0.023636 0.152399 0.052 Uiso 1 1 d G U . . .
H12W H 0.834338 0.329157 0.150310 0.052 Uiso 1 1 d G U . . .
O2W O 0.9613(3) 0.8407(10) 0.4136(3) 0.0390(8) Uani 1 1 d G . . . .
H21W H 0.989869 0.659591 0.452548 0.058 Uiso 1 1 d G U . . .
H22W H 0.892694 0.795021 0.357714 0.058 Uiso 1 1 d G 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
C1 O1 1.325(4) . ?
C1 C6 1.391(6) . ?
C1 C2 1.424(6) . ?
C2 C3 1.377(5) . ?
C2 N1 1.417(5) . ?
C3 C4 1.403(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(6) . ?
C4 C7 1.466(5) . ?
C5 C6 1.390(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N3 1.315(5) . ?
C7 N2 1.325(6) . ?
N1 H1A 0.9096 . ?
N1 H1B 0.9100 . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
O1W H11W 0.8696 . ?
O1W H12W 0.8697 . ?
O2W H21W 0.8696 . ?
O2W H22W 0.8697 . ?

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
O1 C1 C6 122.5(4) . . ?
O1 C1 C2 120.0(4) . . ?
C6 C1 C2 117.4(3) . . ?
C3 C2 N1 121.5(4) . . ?
C3 C2 C1 120.6(4) . . ?
N1 C2 C1 117.9(3) . . ?
C2 C3 C4 121.4(4) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 C7 120.9(4) . . ?
C3 C4 C7 120.8(4) . . ?
C6 C5 C4 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 121.9(4) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
N3 C7 N2 118.7(4) . . ?
N3 C7 C4 121.3(4) . . ?
N2 C7 C4 120.0(4) . . ?
C2 N1 H1A 112.3 . . ?
C2 N1 H1B 104.4 . . ?
H1A N1 H1B 109.5 . . ?
C7 N2 H2A 120.0 . . ?
C7 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C7 N3 H3A 120.0 . . ?
C7 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
H11W O1W H12W 109.5 . . ?
H21W O2W H22W 109.5 . . ?

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 C1 C2 C3 -176.0(4) . . . . ?
C6 C1 C2 C3 1.6(6) . . . . ?
O1 C1 C2 N1 5.1(6) . . . . ?
C6 C1 C2 N1 -177.3(4) . . . . ?
N1 C2 C3 C4 178.8(4) . . . . ?
C1 C2 C3 C4 0.0(7) . . . . ?
C2 C3 C4 C5 -1.8(7) . . . . ?
C2 C3 C4 C7 175.1(4) . . . . ?
C3 C4 C5 C6 2.0(6) . . . . ?
C7 C4 C5 C6 -174.9(4) . . . . ?
C4 C5 C6 C1 -0.5(7) . . . . ?
O1 C1 C6 C5 176.2(4) . . . . ?
C2 C1 C6 C5 -1.3(7) . . . . ?
C5 C4 C7 N3 4.3(7) . . . . ?
C3 C4 C7 N3 -172.5(4) . . . . ?
C5 C4 C7 N2 -176.0(4) . . . . ?
C3 C4 C7 N2 7.1(7) . . . . ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.064

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# 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_8a_I_295K
_database_code_depnum_ccdc_archive 'CCDC 2060885'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C14 H19 N6 O2, Cl, 2(H2 O)'
_chemical_formula_sum            'C14 H23 Cl N6 O4'
_chemical_formula_weight         374.83

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   4.3443(4)
_cell_length_b                   14.5191(9)
_cell_length_c                   15.9472(15)
_cell_angle_alpha                90
_cell_angle_beta                 113.446(11)
_cell_angle_gamma                90
_cell_volume                     922.83(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    869
_cell_measurement_theta_min      4.4200
_cell_measurement_theta_max      30.5400

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.695
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.135
_exptl_absorpt_coefficient_mu    0.239
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.79356
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            3508
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.409
_diffrn_reflns_theta_max         25.239
_diffrn_reflns_theta_full        25.239
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1661
_reflns_number_gt                1235
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2013)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+0.1532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1661
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 1.0529(4) 0.04506(11) 0.25212(11) 0.0419(4) Uani 1 1 d G . . . .
H1A H 1.216783 0.074993 0.299106 0.059(6) Uiso 1 1 d G . . . .
H1B H 1.123348 0.017229 0.212147 0.059(7) Uiso 1 1 d G . . . .
N2 N 0.4623(4) 0.32639(13) 0.32724(12) 0.0529(5) Uani 1 1 d . . . . .
H2A H 0.420756 0.375601 0.350904 0.058(7) Uiso 1 1 calc R . . . .
H2B H 0.565434 0.281152 0.361814 0.090(10) Uiso 1 1 calc R . . . .
N3 N 0.2112(5) 0.38935(13) 0.18593(14) 0.0638(6) Uani 1 1 d . . . . .
H3A H 0.169993 0.438472 0.209790 0.082(8) Uiso 1 1 calc R . . . .
H3B H 0.149211 0.385575 0.127673 0.104(11) Uiso 1 1 calc R . . . .
O1 O 0.6194(3) -0.00243(9) 0.08387(8) 0.0450(4) Uani 1 1 d . . . . .
H1 H 0.500000 0.000000 0.000000 0.105(13) Uiso 1 2 d S . P . .
C4 C 0.4357(5) 0.23683(13) 0.19700(13) 0.0389(5) Uani 1 1 d . . . . .
C5 C 0.2200(5) 0.21052(14) 0.10978(13) 0.0442(5) Uani 1 1 d . . . . .
H5 H 0.034511 0.246851 0.077084 0.053 Uiso 1 1 calc R U . . .
C6 C 0.2779(5) 0.13082(14) 0.07097(13) 0.0431(5) Uani 1 1 d . . . . .
H6 H 0.129858 0.113973 0.012529 0.052 Uiso 1 1 calc R U . . .
C1 C 0.5535(4) 0.07558(13) 0.11789(12) 0.0368(4) Uani 1 1 d . . . . .
C2 C 0.7772(4) 0.10292(12) 0.20588(12) 0.0346(4) Uani 1 1 d . . . . .
C3 C 0.7148(4) 0.18180(13) 0.24472(13) 0.0381(5) Uani 1 1 d . . . . .
H3 H 0.860388 0.198600 0.303435 0.046 Uiso 1 1 calc R U . . .
C7 C 0.3681(5) 0.32032(13) 0.23829(14) 0.0422(5) Uani 1 1 d . . . . .
Cl1 Cl 0.7220(4) 0.13006(10) 0.44877(9) 0.0603(4) Uani 0.42 1 d . . P A 1
Cl2 Cl 1.000000 0.000000 0.500000 0.0615(15) Uani 0.16 2 d S . P B 2
O1W O 0.4773(8) 0.1546(3) 0.4307(2) 0.0687(9) Uani 0.55 1 d G . P C 3
H11W H 0.355299 0.128440 0.451192 0.103 Uiso 0.55 1 d G U P C 3
H12W H 0.623955 0.183023 0.471737 0.103 Uiso 0.55 1 d G U P C 3
O2W O 1.1187(11) 0.0749(3) 0.5008(3) 0.0806(12) Uani 0.45 1 d G . P D 4
H21W H 0.949169 0.046225 0.469554 0.121 Uiso 0.45 1 d G U P D 4
H22W H 1.266666 0.038735 0.530568 0.121 Uiso 0.45 1 d G U P D 4


_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 C2 1.407(2) . ?
N1 H1A 0.9124 . ?
N1 H1B 0.9048 . ?
N2 C7 1.314(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 C7 1.309(2) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
O1 C1 1.335(2) . ?
O1 H1 1.2277 . ?
C4 C5 1.386(3) . ?
C4 C3 1.398(3) . ?
C4 C7 1.464(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C1 1.387(3) . ?
C6 H6 0.9300 . ?
C1 C2 1.409(2) . ?
C2 C3 1.379(2) . ?
C3 H3 0.9300 . ?
O1W H11W 0.8189 . ?
O1W H12W 0.8205 . ?
O2W H21W 0.8199 . ?
O2W H22W 0.8200 . ?

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
C2 N1 H1A 111.7 . . ?
C2 N1 H1B 110.7 . . ?
H1A N1 H1B 114.8 . . ?
C7 N2 H2A 120.0 . . ?
C7 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C7 N3 H3A 120.0 . . ?
C7 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C1 O1 H1 110.63 . . ?
C5 C4 C3 118.85(18) . . ?
C5 C4 C7 120.20(18) . . ?
C3 C4 C7 120.95(17) . . ?
C6 C5 C4 120.62(18) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.96(18) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
O1 C1 C6 123.36(16) . . ?
O1 C1 C2 117.97(16) . . ?
C6 C1 C2 118.66(17) . . ?
C3 C2 N1 122.59(17) . . ?
C3 C2 C1 120.01(17) . . ?
N1 C2 C1 117.36(16) . . ?
C2 C3 C4 120.87(18) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
N3 C7 N2 119.79(19) . . ?
N3 C7 C4 119.60(18) . . ?
N2 C7 C4 120.61(18) . . ?
H11W O1W H12W 109.5 . . ?
H21W O2W H22W 109.5 . . ?

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
C3 C4 C5 C6 0.6(3) . . . . ?
C7 C4 C5 C6 -178.66(16) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C5 C6 C1 O1 179.42(16) . . . . ?
C5 C6 C1 C2 -0.8(3) . . . . ?
O1 C1 C2 C3 -178.39(15) . . . . ?
C6 C1 C2 C3 1.8(3) . . . . ?
O1 C1 C2 N1 -0.8(2) . . . . ?
C6 C1 C2 N1 179.45(15) . . . . ?
N1 C2 C3 C4 -179.14(16) . . . . ?
C1 C2 C3 C4 -1.6(3) . . . . ?
C5 C4 C3 C2 0.4(3) . . . . ?
C7 C4 C3 C2 179.69(16) . . . . ?
C5 C4 C7 N3 -30.1(3) . . . . ?
C3 C4 C7 N3 150.62(19) . . . . ?
C5 C4 C7 N2 149.6(2) . . . . ?
C3 C4 C7 N2 -29.7(3) . . . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.043

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_8b'_123K
_database_code_depnum_ccdc_archive 'CCDC 2060889'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C9 H11 N3 O, 4.335(H2 O), 0.400(O)'
_chemical_formula_sum            'C9 H19.669 N3 O5.735'
_chemical_formula_weight         261.70
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   14.7267(7)
_cell_length_b                   36.3350(18)
_cell_length_c                   7.3619(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.269(4)
_cell_angle_gamma                90
_cell_volume                     3939.3(3)
_cell_formula_units_Z            12
_cell_measurement_temperature    123.0(1)
_cell_measurement_reflns_used    5404
_cell_measurement_theta_min      3.8540
_cell_measurement_theta_max      73.0990

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             1686.6
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    0.940
_shelx_estimated_absorpt_T_min   0.761
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77052
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      123.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.1977
_diffrn_reflns_number            23933
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.864
_diffrn_reflns_theta_max         74.349
_diffrn_reflns_theta_full        67.750
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             7808
_reflns_number_gt                5659
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0876P)²+10.1162P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7808
_refine_ls_number_parameters     942
_refine_ls_number_restraints     2744
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0889
_refine_ls_wR_factor_ref         0.2503
_refine_ls_wR_factor_gt          0.2339
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      0.956
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_vrf_PLAT417_8b'_123K            
;
PROBLEM: Short Inter D-H..H-D       H3D      ..H1B1             2.09 Ang.  
PROBLEM: Short Inter D-H..H-D       H9B      ..H1A4             2.10 Ang.  
PROBLEM: Short Inter D-H..H-D       H12A     ..H13B             2.13 Ang.  
RESPONSE: The two hydrogen atoms belong to two hydrogen-bonded water molecules.
;
# end Validation Reply Form

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
O1S O 0.0779(2) 0.40794(9) 0.4562(6) 0.0326(11) Uani 0.945(12) 1 d G U P A 1
H1A H 0.109697 0.401309 0.366005 0.049 Uiso 0.945(12) 1 d G U P A 1
H1B H 0.115672 0.417739 0.529202 0.049 Uiso 0.945(12) 1 d G U P A 1
O2S O 0.0780(2) 0.42396(9) 0.9491(8) 0.0323(11) Uani 0.929(14) 1 d G U P B 1
H2D H 0.110462 0.431362 0.861176 0.049 Uiso 0.929(14) 1 d G U P B 1
H2E H 0.114690 0.412231 1.017259 0.049 Uiso 0.929(14) 1 d G U P B 1
O3S O 0.3100(2) 0.40928(9) 0.9110(5) 0.0387(7) Uani 1 1 d G . . C 1
H3D H 0.280993 0.421346 0.830627 0.058 Uiso 1 1 d G U . C 1
H3E H 0.270887 0.404861 0.992738 0.058 Uiso 1 1 d G U . C 1
O4S O 0.3107(2) 0.42103(9) 0.4089(5) 0.0401(7) Uani 1 1 d G . . D 1
H4A H 0.276879 0.410201 0.331861 0.060 Uiso 1 1 d G U . D 1
H4B H 0.275579 0.426137 0.496624 0.060 Uiso 1 1 d G U . D 1
O5S O 0.4917(3) 0.21861(10) 0.8060(5) 0.0366(8) Uani 0.796(4) 1 d G U P E 1
H5D H 0.549076 0.221057 0.810905 0.055 Uiso 0.796(4) 1 d DG U P E 1
H5E H 0.472164 0.239927 0.778681 0.055 Uiso 0.796(4) 1 d DG U P E 1
O6S O 0.6708(3) 0.23919(11) 0.7771(6) 0.0361(13) Uani 0.772(12) 1 d DG U P F 1
H6D H 0.703952 0.254791 0.832039 0.054 Uiso 0.772(12) 1 d G U P F 1
H6E H 0.698160 0.235143 0.677727 0.054 Uiso 0.772(12) 1 d DG U P F 1
O7S O 0.9021(2) 0.24207(10) 0.2080(6) 0.0325(13) Uani 0.809(12) 1 d G U P G 1
H7A H 0.862299 0.236533 0.286621 0.049 Uiso 0.809(12) 1 d G U P G 1
H7B H 0.871684 0.250106 0.117893 0.049 Uiso 0.809(12) 1 d G U P G 1
O8S O 0.4194(3) 0.28068(11) 0.6459(8) 0.0291(14) Uani 0.753(16) 1 d DG U P H 1
H8A H 0.456024 0.281318 0.557082 0.044 Uiso 0.753(16) 1 d DG U P H 1
H8B H 0.437717 0.297644 0.716604 0.044 Uiso 0.753(16) 1 d DG U P H 1
O9S O 0.4478(2) 0.34489(9) 0.8289(5) 0.0417(8) Uani 1 1 d DG . . I 1
H9A H 0.453563 0.359305 0.738795 0.063 Uiso 1 1 d G U . I 1
H9B H 0.427772 0.358502 0.913645 0.063 Uiso 1 1 d G U . I 1
O10S O 0.5665(2) 0.37679(10) 0.2647(4) 0.0423(8) Uani 1 1 d G . . J 1
H10A H 0.551491 0.393574 0.189984 0.063 Uiso 1 1 d G U . J 1
H10B H 0.570435 0.357448 0.200335 0.063 Uiso 1 1 d G U . J 1
O11S O 0.4682(2) 0.39787(9) 0.5628(4) 0.0399(7) Uani 1 1 d G . . K 1
H11A H 0.495791 0.392339 0.465347 0.060 Uiso 1 1 d G U . K 1
H11B H 0.415506 0.404361 0.528034 0.060 Uiso 1 1 d G U . K 1
O12S O 0.4715(2) 0.42722(9) 0.0625(4) 0.0407(7) Uani 1 1 d G . . L 1
H12A H 0.499595 0.435807 -0.028676 0.061 Uiso 1 1 d G U . L 1
H12B H 0.418947 0.421956 0.021895 0.061 Uiso 1 1 d G U . L 1
O13S O 0.5677(2) 0.44706(9) 0.7624(5) 0.0383(7) Uani 1 1 d G . . M 1
H13A H 0.561964 0.468887 0.722394 0.057 Uiso 1 1 d G U . M 1
H13B H 0.535187 0.434070 0.691529 0.057 Uiso 1 1 d G U . M 1
O14S O 0.5476(2) 0.51860(9) 0.6811(5) 0.0412(7) Uani 1 1 d G . . N 1
H14A H 0.581916 0.527835 0.600481 0.062 Uiso 1 1 d G U . N 1
H14B H 0.548660 0.534169 0.767304 0.062 Uiso 1 1 d G U . N 1
O1S' O 0.088(3) 0.4073(16) 0.345(10) 0.027(10) Uani 0.055(12) 1 d . U P A 2
O2S' O 0.090(3) 0.4252(15) 0.859(11) 0.0323(11) Uani 0.071(14) 1 d . U P B 2
O5S' O 0.5294(10) 0.2353(4) 0.970(2) 0.0366(8) Uani 0.204(4) 1 d . U P E 2
O5S" O 0.5415(10) 0.1847(4) 0.704(2) 0.0366(8) Uani 0.204(4) 1 d . U P E 2
O6S' O 0.6864(12) 0.2444(5) 0.629(3) 0.062(6) Uani 0.228(12) 1 d . U P F 2
O7S' O 0.9164(12) 0.2401(5) 0.073(4) 0.048(6) Uani 0.191(12) 1 d . U P G 2
O8S' O 0.4277(12) 0.2794(5) 0.762(4) 0.063(6) Uani 0.247(16) 1 d . U P H 2
C1A C 0.1877(2) 0.34811(10) 0.1821(5) 0.0210(8) Uani 0.902(5) 1 d D U P O 1
C2A C 0.2660(2) 0.32499(10) 0.1822(5) 0.0215(8) Uani 0.902(5) 1 d D U P O 1
C3A C 0.2555(3) 0.28735(10) 0.1806(5) 0.0229(9) Uani 0.902(5) 1 d D U P O 1
H3A H 0.308038 0.272167 0.180799 0.027 Uiso 0.902(5) 1 calc R U P O 1
C4A C 0.1697(3) 0.27081(10) 0.1787(6) 0.0224(9) Uani 0.902(5) 1 d D U P O 1
C5A C 0.0930(3) 0.29326(10) 0.1813(6) 0.0246(9) Uani 0.902(5) 1 d D U P O 1
H5A H 0.034182 0.282491 0.183116 0.029 Uiso 0.902(5) 1 calc R U P O 1
C6A C 0.1020(3) 0.33109(10) 0.1815(6) 0.0240(9) Uani 0.902(5) 1 d D U P O 1
H6A H 0.048990 0.345981 0.181106 0.029 Uiso 0.902(5) 1 calc R U P O 1
C7A C 0.1612(2) 0.23108(10) 0.1787(5) 0.0222(8) Uani 0.902(5) 1 d D U P O 1
C8A C 0.2014(3) 0.16974(11) 0.1796(7) 0.0280(10) Uani 0.902(5) 1 d D U P O 1
H8A1 H 0.223874 0.157550 0.291406 0.034 Uiso 0.902(5) 1 calc R U P O 1
H8A2 H 0.222829 0.155836 0.072381 0.034 Uiso 0.902(5) 1 calc R U P O 1
C9A C 0.0973(3) 0.17306(10) 0.1800(7) 0.0289(10) Uani 0.902(5) 1 d D U P O 1
H9A1 H 0.070427 0.162401 0.068272 0.035 Uiso 0.902(5) 1 calc R U P O 1
H9A2 H 0.070812 0.160722 0.287298 0.035 Uiso 0.902(5) 1 calc R U P O 1
N1A N 0.3526(3) 0.34134(11) 0.1789(6) 0.0270(9) Uani 0.902(5) 1 d DG U P O 1
H1A1 H 0.354479 0.363533 0.236055 0.041 Uiso 0.902(5) 1 d DG U P O 1
H1A2 H 0.397246 0.326585 0.223861 0.041 Uiso 0.902(5) 1 d DG U P O 1
N2A N 0.2303(3) 0.20803(10) 0.1720(6) 0.0289(9) Uani 0.902(5) 1 d D U P O 1
H2A H 0.287387 0.214994 0.163915 0.035 Uiso 0.902(5) 1 calc R U P O 1
N3A N 0.0834(2) 0.21284(9) 0.1874(6) 0.0285(9) Uani 0.902(5) 1 d D U P O 1
H3A1 H 0.029893 0.223416 0.196492 0.034 Uiso 0.902(5) 1 calc R U P O 1
O1A O 0.1960(2) 0.38436(8) 0.1824(5) 0.0231(7) Uani 0.902(5) 1 d D U P O 1
C1A' C 0.2009(13) 0.3497(4) 0.099(4) 0.023(4) Uani 0.098(5) 1 d D U P O 2
C2A' C 0.2803(11) 0.3273(5) 0.109(3) 0.024(4) Uani 0.098(5) 1 d D U P O 2
C3A' C 0.2716(12) 0.2895(5) 0.109(4) 0.023(4) Uani 0.098(5) 1 d D U P O 2
H3A' H 0.324699 0.274695 0.114698 0.028 Uiso 0.098(5) 1 calc R U P O 2
C4A' C 0.1867(13) 0.2724(4) 0.100(4) 0.023(4) Uani 0.098(5) 1 d D U P O 2
C5A' C 0.1085(12) 0.2941(5) 0.090(5) 0.022(4) Uani 0.098(5) 1 d D U P O 2
H5A' H 0.050265 0.282903 0.082431 0.026 Uiso 0.098(5) 1 calc R U P O 2
C6A' C 0.1165(12) 0.3320(5) 0.090(5) 0.022(4) Uani 0.098(5) 1 d D U P O 2
H6A' H 0.062978 0.346497 0.083928 0.026 Uiso 0.098(5) 1 calc R U P O 2
C7A' C 0.1791(13) 0.2326(4) 0.098(3) 0.026(4) Uani 0.098(5) 1 d D U P O 2
C8A' C 0.2208(17) 0.1714(5) 0.110(5) 0.028(4) Uani 0.098(5) 1 d D U P O 2
H8A3 H 0.235038 0.158642 0.225046 0.033 Uiso 0.098(5) 1 calc R U P O 2
H8A4 H 0.250617 0.158290 0.008287 0.033 Uiso 0.098(5) 1 calc R U P O 2
C9A' C 0.1179(17) 0.1742(5) 0.079(5) 0.028(4) Uani 0.098(5) 1 d D U P O 2
H9A3 H 0.099817 0.162868 -0.037972 0.033 Uiso 0.098(5) 1 calc R U P O 2
H9A4 H 0.084082 0.162260 0.178759 0.033 Uiso 0.098(5) 1 calc R U P O 2
N1A' N 0.3653(14) 0.3446(7) 0.115(5) 0.029(5) Uani 0.098(5) 1 d DG U P O 2
H1A3 H 0.364870 0.366546 0.174290 0.043 Uiso 0.098(5) 1 d DG U P O 2
H1A4 H 0.410340 0.330150 0.160216 0.043 Uiso 0.098(5) 1 d DG U P O 2
N2A' N 0.2489(13) 0.2099(5) 0.116(5) 0.027(4) Uani 0.098(5) 1 d D U P O 2
H2A' H 0.305417 0.217203 0.131302 0.032 Uiso 0.098(5) 1 calc R U P O 2
N3A' N 0.1027(13) 0.2139(5) 0.077(5) 0.026(4) Uani 0.098(5) 1 d D U P O 2
H3A2 H 0.048949 0.224238 0.063955 0.031 Uiso 0.098(5) 1 calc R U P O 2
O1A' O 0.2074(17) 0.3860(4) 0.098(5) 0.029(5) Uani 0.098(5) 1 d D U P O 2
C1B C 0.1945(4) 0.48364(13) 0.6680(7) 0.0222(11) Uani 0.825(5) 1 d D U P P 1
C2B C 0.2751(4) 0.50548(13) 0.6695(7) 0.0227(10) Uani 0.825(5) 1 d D U P P 1
C3B C 0.2692(4) 0.54310(14) 0.6451(8) 0.0282(12) Uani 0.825(5) 1 d D U P P 1
H3B H 0.323132 0.557423 0.648230 0.034 Uiso 0.825(5) 1 calc R U P P 1
C4B C 0.1858(4) 0.56069(12) 0.6158(8) 0.0246(12) Uani 0.825(5) 1 d D U P P 1
C5B C 0.1063(4) 0.53959(14) 0.6163(11) 0.0276(14) Uani 0.825(5) 1 d D U P P 1
H5B H 0.048953 0.551095 0.599608 0.033 Uiso 0.825(5) 1 calc R U P P 1
C6B C 0.1116(4) 0.50192(15) 0.6413(15) 0.0292(13) Uani 0.825(5) 1 d D U P P 1
H6B H 0.057173 0.487917 0.640267 0.035 Uiso 0.825(5) 1 calc R U P P 1
C7B C 0.1808(3) 0.60019(12) 0.5878(5) 0.0209(9) Uani 0.825(5) 1 d D U P P 1
C8B C 0.2262(3) 0.66056(11) 0.5532(7) 0.0269(10) Uani 0.825(5) 1 d D U P P 1
H8B1 H 0.253190 0.668847 0.437308 0.032 Uiso 0.825(5) 1 calc R U P P 1
H8B2 H 0.245385 0.677437 0.651659 0.032 Uiso 0.825(5) 1 calc R U P P 1
C9B C 0.1222(3) 0.65847(11) 0.5391(7) 0.0256(10) Uani 0.825(5) 1 d D U P P 1
H9B1 H 0.092890 0.671913 0.639985 0.031 Uiso 0.825(5) 1 calc R U P P 1
H9B2 H 0.100178 0.668512 0.421939 0.031 Uiso 0.825(5) 1 calc R U P P 1
N1B N 0.3589(4) 0.48744(17) 0.6822(8) 0.0274(13) Uani 0.825(5) 1 d DG U P P 1
H1B1 H 0.357555 0.467091 0.754165 0.041 Uiso 0.825(5) 1 d DG U P P 1
H1B2 H 0.405371 0.502328 0.717936 0.041 Uiso 0.825(5) 1 d DG U P P 1
N2B N 0.2516(3) 0.62262(11) 0.5941(6) 0.0240(9) Uani 0.825(5) 1 d D U P P 1
H2B H 0.307271 0.615512 0.619943 0.029 Uiso 0.825(5) 1 calc R U P P 1
N3B N 0.1056(3) 0.61884(10) 0.5518(6) 0.0228(9) Uani 0.825(5) 1 d D U P P 1
H3B1 H 0.051904 0.608603 0.537155 0.027 Uiso 0.825(5) 1 calc R U P P 1
O1B O 0.1988(4) 0.44756(11) 0.6860(5) 0.0220(9) Uani 0.825(5) 1 d D U P P 1
C1B' C 0.1941(16) 0.4830(5) 0.629(3) 0.026(4) Uani 0.175(5) 1 d D U P P 2
C2B' C 0.2735(14) 0.5056(5) 0.630(3) 0.027(4) Uani 0.175(5) 1 d D U P P 2
C3B' C 0.2647(14) 0.5434(5) 0.637(3) 0.027(4) Uani 0.175(5) 1 d D U P P 2
H3B' H 0.317828 0.558200 0.636615 0.033 Uiso 0.175(5) 1 calc R U P P 2
C4B' C 0.1795(15) 0.5604(4) 0.645(4) 0.026(4) Uani 0.175(5) 1 d D U P P 2
C5B' C 0.1014(14) 0.5385(5) 0.644(6) 0.028(4) Uani 0.175(5) 1 d D U P P 2
H5B' H 0.043130 0.549632 0.648878 0.034 Uiso 0.175(5) 1 calc R U P P 2
C6B' C 0.1095(15) 0.5006(5) 0.635(6) 0.028(4) Uani 0.175(5) 1 d D U P P 2
H6B' H 0.055888 0.486080 0.633234 0.034 Uiso 0.175(5) 1 calc R U P P 2
C7B' C 0.1727(11) 0.6001(4) 0.650(2) 0.028(3) Uani 0.175(5) 1 d D U P P 2
C8B' C 0.2155(11) 0.6612(4) 0.667(4) 0.035(4) Uani 0.175(5) 1 d D U P P 2
H8B3 H 0.243905 0.674526 0.565152 0.042 Uiso 0.175(5) 1 calc R U P P 2
H8B4 H 0.231712 0.673562 0.782777 0.042 Uiso 0.175(5) 1 calc R U P P 2
C9B' C 0.1121(11) 0.6587(4) 0.643(4) 0.036(4) Uani 0.175(5) 1 d D U P P 2
H9B3 H 0.080030 0.670229 0.746313 0.043 Uiso 0.175(5) 1 calc R U P P 2
H9B4 H 0.092297 0.670692 0.528648 0.043 Uiso 0.175(5) 1 calc R U P P 2
N1B' N 0.3583(16) 0.4881(7) 0.624(4) 0.028(5) Uani 0.175(5) 1 d DG U P P 2
H1B3 H 0.359996 0.466390 0.685322 0.042 Uiso 0.175(5) 1 d DG U P P 2
H1B4 H 0.405153 0.502616 0.660811 0.042 Uiso 0.175(5) 1 d DG U P P 2
N2B' N 0.2429(10) 0.6226(4) 0.670(3) 0.028(4) Uani 0.175(5) 1 d D U P P 2
H2B' H 0.299358 0.615112 0.682699 0.034 Uiso 0.175(5) 1 calc R U P P 2
N3B' N 0.0963(10) 0.6191(4) 0.637(3) 0.034(4) Uani 0.175(5) 1 d D U P P 2
H3B2 H 0.042231 0.608951 0.626709 0.041 Uiso 0.175(5) 1 calc R U P P 2
O1B' O 0.2018(19) 0.4469(5) 0.625(3) 0.029(5) Uani 0.175(5) 1 d D U P P 2
C1C C 0.7924(3) 0.31785(10) 0.9660(6) 0.0226(9) Uani 0.825(5) 1 d D U P P 1
C2C C 0.7141(3) 0.34086(11) 0.9491(5) 0.0226(9) Uani 0.825(5) 1 d D U P P 1
C3C C 0.7243(3) 0.37832(11) 0.9235(6) 0.0223(9) Uani 0.825(5) 1 d D U P P 1
H3C H 0.671773 0.393319 0.911149 0.027 Uiso 0.825(5) 1 calc R U P P 1
C4C C 0.8103(3) 0.39460(11) 0.9153(6) 0.0211(10) Uani 0.825(5) 1 d D U P P 1
C5C C 0.8873(3) 0.37238(11) 0.9345(6) 0.0209(9) Uani 0.825(5) 1 d D U P P 1
H5C H 0.946117 0.383102 0.930919 0.025 Uiso 0.825(5) 1 calc R U P P 1
C6C C 0.8779(3) 0.33482(11) 0.9586(6) 0.0220(9) Uani 0.825(5) 1 d D U P P 1
H6C H 0.930929 0.320082 0.970450 0.026 Uiso 0.825(5) 1 calc R U P P 1
C7C C 0.8196(3) 0.43398(12) 0.8907(7) 0.0225(11) Uani 0.825(5) 1 d D U P P 1
C8C C 0.7805(6) 0.49461(15) 0.842(2) 0.0292(16) Uani 0.825(5) 1 d D U P P 1
H8C1 H 0.751810 0.510310 0.935704 0.035 Uiso 0.825(5) 1 calc R U P P 1
H8C2 H 0.766270 0.504678 0.720421 0.035 Uiso 0.825(5) 1 calc R U P P 1
C9C C 0.8834(6) 0.49179(15) 0.8726(14) 0.0299(16) Uani 0.825(5) 1 d D U P P 1
H9C1 H 0.917237 0.500943 0.765870 0.036 Uiso 0.825(5) 1 calc R U P P 1
H9C2 H 0.902615 0.505797 0.981592 0.036 Uiso 0.825(5) 1 calc R U P P 1
N1C N 0.6281(3) 0.32521(11) 0.9717(7) 0.0316(10) Uani 0.825(5) 1 d DG U P P 1
H1C1 H 0.625211 0.300754 0.945474 0.047 Uiso 0.825(5) 1 d DG U P P 1
H1C2 H 0.583514 0.337327 0.910143 0.047 Uiso 0.825(5) 1 d DG U P P 1
N2C N 0.7506(4) 0.45645(15) 0.8582(15) 0.0286(16) Uani 0.825(5) 1 d D U P P 1
H2C H 0.693778 0.449261 0.847589 0.034 Uiso 0.825(5) 1 calc R U P P 1
N3C N 0.8972(4) 0.45229(14) 0.8981(9) 0.0255(13) Uani 0.825(5) 1 d D U P P 1
H3C1 H 0.950517 0.441965 0.916193 0.031 Uiso 0.825(5) 1 calc R U P P 1
O1C O 0.7832(2) 0.28211(8) 0.9894(5) 0.0275(8) Uani 0.825(5) 1 d D U P P 1
C1C' C 0.8074(8) 0.3176(3) 0.849(2) 0.031(3) Uani 0.175(5) 1 d D U P P 2
C2C' C 0.7282(7) 0.3401(3) 0.844(2) 0.029(3) Uani 0.175(5) 1 d D U P P 2
C3C' C 0.7369(9) 0.3779(3) 0.845(2) 0.028(4) Uani 0.175(5) 1 d D U P P 2
H3C' H 0.683880 0.392736 0.837580 0.033 Uiso 0.175(5) 1 calc R U P P 2
C4C' C 0.8219(10) 0.3949(3) 0.856(3) 0.024(3) Uani 0.175(5) 1 d D U P P 2
C5C' C 0.9002(10) 0.3731(4) 0.856(3) 0.029(4) Uani 0.175(5) 1 d D U P P 2
H5C' H 0.958581 0.384274 0.855437 0.034 Uiso 0.175(5) 1 calc R U P P 2
C6C' C 0.8919(9) 0.3353(4) 0.856(3) 0.034(3) Uani 0.175(5) 1 d D U P P 2
H6C' H 0.945383 0.320704 0.860899 0.040 Uiso 0.175(5) 1 calc R U P P 2
C7C' C 0.8308(14) 0.4346(4) 0.849(3) 0.024(4) Uani 0.175(5) 1 d D U P P 2
C8C' C 0.794(3) 0.4961(5) 0.831(9) 0.027(4) Uani 0.175(5) 1 d D U P P 2
H8C3 H 0.768447 0.510222 0.934667 0.032 Uiso 0.175(5) 1 calc R U P P 2
H8C4 H 0.776363 0.508484 0.716356 0.032 Uiso 0.175(5) 1 calc R U P P 2
C9C' C 0.897(3) 0.4922(6) 0.848(7) 0.028(4) Uani 0.175(5) 1 d D U P P 2
H9C3 H 0.928113 0.502759 0.741154 0.033 Uiso 0.175(5) 1 calc R U P P 2
H9C4 H 0.920147 0.504297 0.959545 0.033 Uiso 0.175(5) 1 calc R U P P 2
N1C' N 0.6434(9) 0.3224(4) 0.842(3) 0.030(4) Uani 0.175(5) 1 d DG U P P 2
H1C3 H 0.642939 0.301311 0.775011 0.045 Uiso 0.175(5) 1 d DG U P P 2
H1C4 H 0.597115 0.337227 0.805119 0.045 Uiso 0.175(5) 1 d DG U P P 2
N2C' N 0.7624(18) 0.4580(6) 0.834(7) 0.027(4) Uani 0.175(5) 1 d D U P P 2
H2C' H 0.705049 0.451379 0.826206 0.032 Uiso 0.175(5) 1 calc R U P P 2
N3C' N 0.9092(16) 0.4524(6) 0.857(5) 0.028(4) Uani 0.175(5) 1 d D U P P 2
H3C2 H 0.962321 0.441428 0.865992 0.034 Uiso 0.175(5) 1 calc R U P P 2
O1C' O 0.8002(10) 0.2814(3) 0.848(2) 0.035(3) Uani 0.175(5) 1 d D U P P 2


_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
O1S H1A 0.8498 . ?
O1S H1B 0.8501 . ?
O2S H2D 0.8499 . ?
O2S H2E 0.8500 . ?
O3S H3D 0.8499 . ?
O3S H3E 0.8500 . ?
O4S H4A 0.8502 . ?
O4S H4B 0.8500 . ?
O5S H5D 0.8499 . ?
O5S H5E 0.8501 . ?
O6S H6D 0.8497 . ?
O6S H6E 0.8500 . ?
O7S H7A 0.8500 . ?
O7S H7B 0.8501 . ?
O8S H8A 0.8499 . ?
O8S H8B 0.8502 . ?
O9S H9A 0.8499 . ?
O9S H9B 0.8500 . ?
O10S H10A 0.8500 . ?
O10S H10B 0.8499 . ?
O11S H11A 0.8500 . ?
O11S H11B 0.8499 . ?
O12S H12A 0.8500 . ?
O12S H12B 0.8500 . ?
O13S H13A 0.8500 . ?
O13S H13B 0.8500 . ?
O14S H14A 0.8501 . ?
O14S H14B 0.8501 . ?
C1A O1A 1.323(4) . ?
C1A C6A 1.405(5) . ?
C1A C2A 1.427(5) . ?
C2A C3A 1.376(5) . ?
C2A N1A 1.407(4) . ?
C3A C4A 1.399(5) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.394(5) . ?
C4A C7A 1.449(5) . ?
C5A C6A 1.381(5) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A N2A 1.319(4) . ?
C7A N3A 1.325(4) . ?
C8A N2A 1.456(5) . ?
C8A C9A 1.538(5) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A N3A 1.461(4) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
N1A H1A1 0.9100 . ?
N1A H1A2 0.9099 . ?
N2A H2A 0.8800 . ?
N3A H3A1 0.8800 . ?
C1A' O1A' 1.320(8) . ?
C1A' C6A' 1.402(8) . ?
C1A' C2A' 1.427(8) . ?
C2A' C3A' 1.379(8) . ?
C2A' N1A' 1.401(8) . ?
C3A' C4A' 1.398(8) . ?
C3A' H3A' 0.9500 . ?
C4A' C5A' 1.398(8) . ?
C4A' C7A' 1.449(8) . ?
C5A' C6A' 1.381(8) . ?
C5A' H5A' 0.9500 . ?
C6A' H6A' 0.9500 . ?
C7A' N3A' 1.323(7) . ?
C7A' N2A' 1.323(7) . ?
C8A' N2A' 1.459(8) . ?
C8A' C9A' 1.534(9) . ?
C8A' H8A3 0.9900 . ?
C8A' H8A4 0.9900 . ?
C9A' N3A' 1.461(8) . ?
C9A' H9A3 0.9900 . ?
C9A' H9A4 0.9900 . ?
N1A' H1A3 0.9101 . ?
N1A' H1A4 0.9100 . ?
N2A' H2A' 0.8800 . ?
N3A' H3A2 0.8800 . ?
C1B O1B 1.319(5) . ?
C1B C6B 1.403(5) . ?
C1B C2B 1.427(5) . ?
C2B C3B 1.382(5) . ?
C2B N1B 1.401(5) . ?
C3B C4B 1.399(5) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.400(5) . ?
C4B C7B 1.452(5) . ?
C5B C6B 1.383(5) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B N2B 1.323(5) . ?
C7B N3B 1.324(5) . ?
C8B N2B 1.459(5) . ?
C8B C9B 1.535(5) . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9B N3B 1.464(5) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
N1B H1B1 0.9099 . ?
N1B H1B2 0.9100 . ?
N2B H2B 0.8800 . ?
N3B H3B1 0.8800 . ?
C1B' O1B' 1.318(8) . ?
C1B' C6B' 1.402(8) . ?
C1B' C2B' 1.429(8) . ?
C2B' C3B' 1.378(8) . ?
C2B' N1B' 1.402(8) . ?
C3B' C4B' 1.400(8) . ?
C3B' H3B' 0.9500 . ?
C4B' C5B' 1.397(8) . ?
C4B' C7B' 1.450(7) . ?
C5B' C6B' 1.383(8) . ?
C5B' H5B' 0.9500 . ?
C6B' H6B' 0.9500 . ?
C7B' N3B' 1.322(7) . ?
C7B' N2B' 1.323(7) . ?
C8B' N2B' 1.459(8) . ?
C8B' C9B' 1.535(9) . ?
C8B' H8B3 0.9900 . ?
C8B' H8B4 0.9900 . ?
C9B' N3B' 1.460(8) . ?
C9B' H9B3 0.9900 . ?
C9B' H9B4 0.9900 . ?
N1B' H1B3 0.9103 . ?
N1B' H1B4 0.9099 . ?
N2B' H2B' 0.8800 . ?
N3B' H3B2 0.8800 . ?
C1C O1C 1.317(4) . ?
C1C C6C 1.403(5) . ?
C1C C2C 1.429(5) . ?
C2C C3C 1.382(5) . ?
C2C N1C 1.399(5) . ?
C3C C4C 1.400(5) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.399(5) . ?
C4C C7C 1.449(5) . ?
C5C C6C 1.383(5) . ?
C5C H5C 0.9500 . ?
C6C H6C 0.9500 . ?
C7C N3C 1.323(5) . ?
C7C N2C 1.325(5) . ?
C8C N2C 1.460(5) . ?
C8C C9C 1.535(6) . ?
C8C H8C1 0.9900 . ?
C8C H8C2 0.9900 . ?
C9C N3C 1.461(5) . ?
C9C H9C1 0.9900 . ?
C9C H9C2 0.9900 . ?
N1C H1C1 0.9102 . ?
N1C H1C2 0.9101 . ?
N2C H2C 0.8800 . ?
N3C H3C1 0.8800 . ?
C1C' O1C' 1.318(8) . ?
C1C' C6C' 1.401(8) . ?
C1C' C2C' 1.426(8) . ?
C2C' C3C' 1.379(8) . ?
C2C' N1C' 1.404(8) . ?
C3C' C4C' 1.398(8) . ?
C3C' H3C' 0.9500 . ?
C4C' C5C' 1.398(8) . ?
C4C' C7C' 1.450(7) . ?
C5C' C6C' 1.381(8) . ?
C5C' H5C' 0.9500 . ?
C6C' H6C' 0.9500 . ?
C7C' N2C' 1.322(7) . ?
C7C' N3C' 1.323(7) . ?
C8C' N2C' 1.460(8) . ?
C8C' C9C' 1.534(9) . ?
C8C' H8C3 0.9900 . ?
C8C' H8C4 0.9900 . ?
C9C' N3C' 1.460(8) . ?
C9C' H9C3 0.9900 . ?
C9C' H9C4 0.9900 . ?
N1C' H1C3 0.9101 . ?
N1C' H1C4 0.9102 . ?
N2C' H2C' 0.8800 . ?
N3C' H3C2 0.8800 . ?

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
H1A O1S H1B 104.5 . . ?
H2D O2S H2E 104.5 . . ?
H3D O3S H3E 104.5 . . ?
H4A O4S H4B 104.5 . . ?
H5D O5S H5E 104.5 . . ?
H6D O6S H6E 104.5 . . ?
H7A O7S H7B 104.5 . . ?
H8A O8S H8B 104.5 . . ?
H9A O9S H9B 104.5 . . ?
H10A O10S H10B 104.5 . . ?
H11A O11S H11B 104.5 . . ?
H12A O12S H12B 104.5 . . ?
H13A O13S H13B 104.5 . . ?
H14A O14S H14B 104.5 . . ?
O1A C1A C6A 121.4(3) . . ?
O1A C1A C2A 120.8(3) . . ?
C6A C1A C2A 117.8(3) . . ?
C3A C2A N1A 121.4(3) . . ?
C3A C2A C1A 119.6(3) . . ?
N1A C2A C1A 118.9(3) . . ?
C2A C3A C4A 121.9(3) . . ?
C2A C3A H3A 119.1 . . ?
C4A C3A H3A 119.1 . . ?
C5A C4A C3A 118.7(3) . . ?
C5A C4A C7A 120.9(3) . . ?
C3A C4A C7A 120.4(3) . . ?
C6A C5A C4A 120.3(3) . . ?
C6A C5A H5A 119.9 . . ?
C4A C5A H5A 119.9 . . ?
C5A C6A C1A 121.7(3) . . ?
C5A C6A H6A 119.2 . . ?
C1A C6A H6A 119.2 . . ?
N2A C7A N3A 110.6(3) . . ?
N2A C7A C4A 124.5(3) . . ?
N3A C7A C4A 124.9(3) . . ?
N2A C8A C9A 102.5(3) . . ?
N2A C8A H8A1 111.3 . . ?
C9A C8A H8A1 111.3 . . ?
N2A C8A H8A2 111.3 . . ?
C9A C8A H8A2 111.3 . . ?
H8A1 C8A H8A2 109.2 . . ?
N3A C9A C8A 102.6(3) . . ?
N3A C9A H9A1 111.3 . . ?
C8A C9A H9A1 111.3 . . ?
N3A C9A H9A2 111.3 . . ?
C8A C9A H9A2 111.3 . . ?
H9A1 C9A H9A2 109.2 . . ?
C2A N1A H1A1 113.1 . . ?
C2A N1A H1A2 113.5 . . ?
H1A1 N1A H1A2 109.5 . . ?
C7A N2A C8A 112.3(3) . . ?
C7A N2A H2A 123.8 . . ?
C8A N2A H2A 123.8 . . ?
C7A N3A C9A 111.8(3) . . ?
C7A N3A H3A1 124.1 . . ?
C9A N3A H3A1 124.1 . . ?
O1A' C1A' C6A' 121.6(11) . . ?
O1A' C1A' C2A' 120.7(10) . . ?
C6A' C1A' C2A' 117.7(8) . . ?
C3A' C2A' N1A' 122.1(10) . . ?
C3A' C2A' C1A' 119.5(7) . . ?
N1A' C2A' C1A' 118.4(10) . . ?
C2A' C3A' C4A' 121.8(9) . . ?
C2A' C3A' H3A' 119.1 . . ?
C4A' C3A' H3A' 119.1 . . ?
C5A' C4A' C3A' 119.2(9) . . ?
C5A' C4A' C7A' 120.0(9) . . ?
C3A' C4A' C7A' 120.8(9) . . ?
C6A' C5A' C4A' 119.5(10) . . ?
C6A' C5A' H5A' 120.3 . . ?
C4A' C5A' H5A' 120.3 . . ?
C5A' C6A' C1A' 122.4(10) . . ?
C5A' C6A' H6A' 118.8 . . ?
C1A' C6A' H6A' 118.8 . . ?
N3A' C7A' N2A' 110.7(8) . . ?
N3A' C7A' C4A' 125.3(9) . . ?
N2A' C7A' C4A' 124.1(9) . . ?
N2A' C8A' C9A' 102.8(7) . . ?
N2A' C8A' H8A3 111.2 . . ?
C9A' C8A' H8A3 111.2 . . ?
N2A' C8A' H8A4 111.2 . . ?
C9A' C8A' H8A4 111.2 . . ?
H8A3 C8A' H8A4 109.1 . . ?
N3A' C9A' C8A' 102.6(6) . . ?
N3A' C9A' H9A3 111.2 . . ?
C8A' C9A' H9A3 111.2 . . ?
N3A' C9A' H9A4 111.2 . . ?
C8A' C9A' H9A4 111.2 . . ?
H9A3 C9A' H9A4 109.2 . . ?
C2A' N1A' H1A3 113.6 . . ?
C2A' N1A' H1A4 113.7 . . ?
H1A3 N1A' H1A4 109.5 . . ?
C7A' N2A' C8A' 111.9(8) . . ?
C7A' N2A' H2A' 124.0 . . ?
C8A' N2A' H2A' 124.0 . . ?
C7A' N3A' C9A' 112.0(8) . . ?
C7A' N3A' H3A2 124.0 . . ?
C9A' N3A' H3A2 124.0 . . ?
O1B C1B C6B 121.8(4) . . ?
O1B C1B C2B 120.8(4) . . ?
C6B C1B C2B 117.4(4) . . ?
C3B C2B N1B 121.8(4) . . ?
C3B C2B C1B 119.8(4) . . ?
N1B C2B C1B 118.2(4) . . ?
C2B C3B C4B 121.8(4) . . ?
C2B C3B H3B 119.1 . . ?
C4B C3B H3B 119.1 . . ?
C3B C4B C5B 118.9(4) . . ?
C3B C4B C7B 121.1(4) . . ?
C5B C4B C7B 120.0(4) . . ?
C6B C5B C4B 119.7(4) . . ?
C6B C5B H5B 120.2 . . ?
C4B C5B H5B 120.2 . . ?
C5B C6B C1B 122.4(4) . . ?
C5B C6B H6B 118.8 . . ?
C1B C6B H6B 118.8 . . ?
N2B C7B N3B 110.5(4) . . ?
N2B C7B C4B 124.4(4) . . ?
N3B C7B C4B 125.2(4) . . ?
N2B C8B C9B 102.8(3) . . ?
N2B C8B H8B1 111.2 . . ?
C9B C8B H8B1 111.2 . . ?
N2B C8B H8B2 111.2 . . ?
C9B C8B H8B2 111.2 . . ?
H8B1 C8B H8B2 109.1 . . ?
N3B C9B C8B 102.2(3) . . ?
N3B C9B H9B1 111.3 . . ?
C8B C9B H9B1 111.3 . . ?
N3B C9B H9B2 111.3 . . ?
C8B C9B H9B2 111.3 . . ?
H9B1 C9B H9B2 109.2 . . ?
C2B N1B H1B1 113.4 . . ?
C2B N1B H1B2 113.7 . . ?
H1B1 N1B H1B2 109.5 . . ?
C7B N2B C8B 111.9(4) . . ?
C7B N2B H2B 124.0 . . ?
C8B N2B H2B 124.0 . . ?
C7B N3B C9B 112.1(3) . . ?
C7B N3B H3B1 124.0 . . ?
C9B N3B H3B1 124.0 . . ?
O1B' C1B' C6B' 122.2(11) . . ?
O1B' C1B' C2B' 120.1(10) . . ?
C6B' C1B' C2B' 117.7(8) . . ?
C3B' C2B' N1B' 122.5(9) . . ?
C3B' C2B' C1B' 119.6(7) . . ?
N1B' C2B' C1B' 117.9(10) . . ?
C2B' C3B' C4B' 121.7(9) . . ?
C2B' C3B' H3B' 119.2 . . ?
C4B' C3B' H3B' 119.2 . . ?
C5B' C4B' C3B' 119.1(9) . . ?
C5B' C4B' C7B' 120.6(9) . . ?
C3B' C4B' C7B' 120.2(9) . . ?
C6B' C5B' C4B' 119.7(10) . . ?
C6B' C5B' H5B' 120.2 . . ?
C4B' C5B' H5B' 120.2 . . ?
C5B' C6B' C1B' 122.1(10) . . ?
C5B' C6B' H6B' 118.9 . . ?
C1B' C6B' H6B' 118.9 . . ?
N3B' C7B' N2B' 110.6(8) . . ?
N3B' C7B' C4B' 125.2(9) . . ?
N2B' C7B' C4B' 124.3(9) . . ?
N2B' C8B' C9B' 102.7(6) . . ?
N2B' C8B' H8B3 111.2 . . ?
C9B' C8B' H8B3 111.2 . . ?
N2B' C8B' H8B4 111.2 . . ?
C9B' C8B' H8B4 111.2 . . ?
H8B3 C8B' H8B4 109.1 . . ?
N3B' C9B' C8B' 102.6(6) . . ?
N3B' C9B' H9B3 111.2 . . ?
C8B' C9B' H9B3 111.2 . . ?
N3B' C9B' H9B4 111.2 . . ?
C8B' C9B' H9B4 111.2 . . ?
H9B3 C9B' H9B4 109.2 . . ?
C2B' N1B' H1B3 113.6 . . ?
C2B' N1B' H1B4 113.7 . . ?
H1B3 N1B' H1B4 109.5 . . ?
C7B' N2B' C8B' 112.0(7) . . ?
C7B' N2B' H2B' 124.0 . . ?
C8B' N2B' H2B' 124.0 . . ?
C7B' N3B' C9B' 112.1(7) . . ?
C7B' N3B' H3B2 124.0 . . ?
C9B' N3B' H3B2 124.0 . . ?
O1C C1C C6C 122.1(4) . . ?
O1C C1C C2C 120.3(3) . . ?
C6C C1C C2C 117.6(3) . . ?
C3C C2C N1C 121.0(4) . . ?
C3C C2C C1C 120.0(3) . . ?
N1C C2C C1C 118.8(3) . . ?
C2C C3C C4C 121.4(4) . . ?
C2C C3C H3C 119.3 . . ?
C4C C3C H3C 119.3 . . ?
C5C C4C C3C 119.0(4) . . ?
C5C C4C C7C 120.3(4) . . ?
C3C C4C C7C 120.6(4) . . ?
C6C C5C C4C 120.1(4) . . ?
C6C C5C H5C 120.0 . . ?
C4C C5C H5C 120.0 . . ?
C5C C6C C1C 121.9(4) . . ?
C5C C6C H6C 119.0 . . ?
C1C C6C H6C 119.0 . . ?
N3C C7C N2C 111.0(4) . . ?
N3C C7C C4C 125.1(4) . . ?
N2C C7C C4C 123.9(4) . . ?
N2C C8C C9C 102.9(3) . . ?
N2C C8C H8C1 111.2 . . ?
C9C C8C H8C1 111.2 . . ?
N2C C8C H8C2 111.2 . . ?
C9C C8C H8C2 111.2 . . ?
H8C1 C8C H8C2 109.1 . . ?
N3C C9C C8C 102.7(3) . . ?
N3C C9C H9C1 111.2 . . ?
C8C C9C H9C1 111.2 . . ?
N3C C9C H9C2 111.2 . . ?
C8C C9C H9C2 111.2 . . ?
H9C1 C9C H9C2 109.1 . . ?
C2C N1C H1C1 114.4 . . ?
C2C N1C H1C2 113.3 . . ?
H1C1 N1C H1C2 109.5 . . ?
C7C N2C C8C 111.6(4) . . ?
C7C N2C H2C 124.2 . . ?
C8C N2C H2C 124.2 . . ?
C7C N3C C9C 111.7(4) . . ?
C7C N3C H3C1 124.2 . . ?
C9C N3C H3C1 124.2 . . ?
O1C' C1C' C6C' 122.0(9) . . ?
O1C' C1C' C2C' 120.4(9) . . ?
C6C' C1C' C2C' 117.6(8) . . ?
C3C' C2C' N1C' 122.7(8) . . ?
C3C' C2C' C1C' 119.7(7) . . ?
N1C' C2C' C1C' 117.6(9) . . ?
C2C' C3C' C4C' 121.6(8) . . ?
C2C' C3C' H3C' 119.2 . . ?
C4C' C3C' H3C' 119.2 . . ?
C5C' C4C' C3C' 119.2(9) . . ?
C5C' C4C' C7C' 119.3(9) . . ?
C3C' C4C' C7C' 121.2(9) . . ?
C6C' C5C' C4C' 119.3(9) . . ?
C6C' C5C' H5C' 120.3 . . ?
C4C' C5C' H5C' 120.3 . . ?
C5C' C6C' C1C' 122.4(9) . . ?
C5C' C6C' H6C' 118.8 . . ?
C1C' C6C' H6C' 118.8 . . ?
N2C' C7C' N3C' 110.8(8) . . ?
N2C' C7C' C4C' 125.0(10) . . ?
N3C' C7C' C4C' 124.2(10) . . ?
N2C' C8C' C9C' 102.8(7) . . ?
N2C' C8C' H8C3 111.2 . . ?
C9C' C8C' H8C3 111.2 . . ?
N2C' C8C' H8C4 111.2 . . ?
C9C' C8C' H8C4 111.2 . . ?
H8C3 C8C' H8C4 109.1 . . ?
N3C' C9C' C8C' 102.6(7) . . ?
N3C' C9C' H9C3 111.3 . . ?
C8C' C9C' H9C3 111.3 . . ?
N3C' C9C' H9C4 111.3 . . ?
C8C' C9C' H9C4 111.3 . . ?
H9C3 C9C' H9C4 109.2 . . ?
C2C' N1C' H1C3 113.3 . . ?
C2C' N1C' H1C4 113.3 . . ?
H1C3 N1C' H1C4 109.5 . . ?
C7C' N2C' C8C' 111.8(8) . . ?
C7C' N2C' H2C' 124.1 . . ?
C8C' N2C' H2C' 124.1 . . ?
C7C' N3C' C9C' 112.0(8) . . ?
C7C' N3C' H3C2 124.0 . . ?
C9C' N3C' H3C2 124.0 . . ?

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
O1A C1A C2A C3A -179.5(3) . . . . ?
C6A C1A C2A C3A 0.4(4) . . . . ?
O1A C1A C2A N1A -1.3(5) . . . . ?
C6A C1A C2A N1A 178.6(4) . . . . ?
N1A C2A C3A C4A -178.1(4) . . . . ?
C1A C2A C3A C4A 0.0(4) . . . . ?
C2A C3A C4A C5A -1.0(5) . . . . ?
C2A C3A C4A C7A -179.4(3) . . . . ?
C3A C4A C5A C6A 1.6(6) . . . . ?
C7A C4A C5A C6A 179.9(4) . . . . ?
C4A C5A C6A C1A -1.1(6) . . . . ?
O1A C1A C6A C5A -179.9(4) . . . . ?
C2A C1A C6A C5A 0.1(6) . . . . ?
C5A C4A C7A N2A 178.3(4) . . . . ?
C3A C4A C7A N2A -3.3(5) . . . . ?
C5A C4A C7A N3A -2.4(6) . . . . ?
C3A C4A C7A N3A 176.0(4) . . . . ?
N2A C8A C9A N3A -4.4(4) . . . . ?
N3A C7A N2A C8A -1.1(5) . . . . ?
C4A C7A N2A C8A 178.2(3) . . . . ?
C9A C8A N2A C7A 3.6(5) . . . . ?
N2A C7A N3A C9A -2.2(5) . . . . ?
C4A C7A N3A C9A 178.5(3) . . . . ?
C8A C9A N3A C7A 4.2(5) . . . . ?
O1A' C1A' C2A' C3A' -179.7(14) . . . . ?
C6A' C1A' C2A' C3A' -0.1(13) . . . . ?
O1A' C1A' C2A' N1A' -0.7(18) . . . . ?
C6A' C1A' C2A' N1A' 178.9(18) . . . . ?
N1A' C2A' C3A' C4A' -179.0(18) . . . . ?
C1A' C2A' C3A' C4A' -0.1(11) . . . . ?
C2A' C3A' C4A' C5A' 0(3) . . . . ?
C2A' C3A' C4A' C7A' 179.2(12) . . . . ?
C3A' C4A' C5A' C6A' -1(3) . . . . ?
C7A' C4A' C5A' C6A' -179(2) . . . . ?
C4A' C5A' C6A' C1A' 0(4) . . . . ?
O1A' C1A' C6A' C5A' 179(2) . . . . ?
C2A' C1A' C6A' C5A' 0(3) . . . . ?
C5A' C4A' C7A' N3A' 4(3) . . . . ?
C3A' C4A' C7A' N3A' -175(2) . . . . ?
C5A' C4A' C7A' N2A' -176(3) . . . . ?
C3A' C4A' C7A' N2A' 5(2) . . . . ?
N2A' C8A' C9A' N3A' -1(2) . . . . ?
N3A' C7A' N2A' C8A' -0.2(19) . . . . ?
C4A' C7A' N2A' C8A' 179.7(13) . . . . ?
C9A' C8A' N2A' C7A' 1(2) . . . . ?
N2A' C7A' N3A' C9A' -1(2) . . . . ?
C4A' C7A' N3A' C9A' 179.4(14) . . . . ?
C8A' C9A' N3A' C7A' 1(3) . . . . ?
O1B C1B C2B C3B 178.1(4) . . . . ?
C6B C1B C2B C3B 0.0(6) . . . . ?
O1B C1B C2B N1B 2.8(6) . . . . ?
C6B C1B C2B N1B -175.2(6) . . . . ?
N1B C2B C3B C4B 174.0(5) . . . . ?
C1B C2B C3B C4B -1.0(5) . . . . ?
C2B C3B C4B C5B 1.8(7) . . . . ?
C2B C3B C4B C7B -179.2(4) . . . . ?
C3B C4B C5B C6B -1.5(9) . . . . ?
C7B C4B C5B C6B 179.4(6) . . . . ?
C4B C5B C6B C1B 0.6(11) . . . . ?
O1B C1B C6B C5B -177.8(7) . . . . ?
C2B C1B C6B C5B 0.2(10) . . . . ?
C3B C4B C7B N2B -2.6(7) . . . . ?
C5B C4B C7B N2B 176.5(5) . . . . ?
C3B C4B C7B N3B 177.0(5) . . . . ?
C5B C4B C7B N3B -3.9(7) . . . . ?
N2B C8B C9B N3B -6.8(5) . . . . ?
N3B C7B N2B C8B -2.1(5) . . . . ?
C4B C7B N2B C8B 177.6(4) . . . . ?
C9B C8B N2B C7B 5.8(5) . . . . ?
N2B C7B N3B C9B -2.9(5) . . . . ?
C4B C7B N3B C9B 177.4(4) . . . . ?
C8B C9B N3B C7B 6.2(5) . . . . ?
O1B' C1B' C2B' C3B' -179.0(14) . . . . ?
C6B' C1B' C2B' C3B' 0.1(14) . . . . ?
O1B' C1B' C2B' N1B' 1.0(19) . . . . ?
C6B' C1B' C2B' N1B' -180.0(19) . . . . ?
N1B' C2B' C3B' C4B' -179.4(18) . . . . ?
C1B' C2B' C3B' C4B' 0.6(11) . . . . ?
C2B' C3B' C4B' C5B' -1(3) . . . . ?
C2B' C3B' C4B' C7B' -179.1(12) . . . . ?
C3B' C4B' C5B' C6B' 0(4) . . . . ?
C7B' C4B' C5B' C6B' 179(2) . . . . ?
C4B' C5B' C6B' C1B' 1(4) . . . . ?
O1B' C1B' C6B' C5B' 178(2) . . . . ?
C2B' C1B' C6B' C5B' -1(3) . . . . ?
C5B' C4B' C7B' N3B' -6(2) . . . . ?
C3B' C4B' C7B' N3B' 172(2) . . . . ?
C5B' C4B' C7B' N2B' 173(2) . . . . ?
C3B' C4B' C7B' N2B' -9(2) . . . . ?
N2B' C8B' C9B' N3B' 1(2) . . . . ?
N3B' C7B' N2B' C8B' -1.5(17) . . . . ?
C4B' C7B' N2B' C8B' 179.4(11) . . . . ?
C9B' C8B' N2B' C7B' 0.4(18) . . . . ?
N2B' C7B' N3B' C9B' 2(2) . . . . ?
C4B' C7B' N3B' C9B' -178.9(12) . . . . ?
C8B' C9B' N3B' C7B' -2(2) . . . . ?
O1C C1C C2C C3C -179.6(4) . . . . ?
C6C C1C C2C C3C 1.0(5) . . . . ?
O1C C1C C2C N1C 4.8(5) . . . . ?
C6C C1C C2C N1C -174.5(4) . . . . ?
N1C C2C C3C C4C 174.8(4) . . . . ?
C1C C2C C3C C4C -0.7(5) . . . . ?
C2C C3C C4C C5C -0.3(6) . . . . ?
C2C C3C C4C C7C -179.2(4) . . . . ?
C3C C4C C5C C6C 0.9(7) . . . . ?
C7C C4C C5C C6C 179.8(4) . . . . ?
C4C C5C C6C C1C -0.5(7) . . . . ?
O1C C1C C6C C5C -179.8(4) . . . . ?
C2C C1C C6C C5C -0.5(6) . . . . ?
C5C C4C C7C N3C -5.5(7) . . . . ?
C3C C4C C7C N3C 173.4(5) . . . . ?
C5C C4C C7C N2C 174.8(6) . . . . ?
C3C C4C C7C N2C -6.3(7) . . . . ?
N2C C8C C9C N3C 1.0(7) . . . . ?
N3C C7C N2C C8C -0.6(7) . . . . ?
C4C C7C N2C C8C 179.2(5) . . . . ?
C9C C8C N2C C7C -0.3(7) . . . . ?
N2C C7C N3C C9C 1.3(7) . . . . ?
C4C C7C N3C C9C -178.4(5) . . . . ?
C8C C9C N3C C7C -1.5(7) . . . . ?
O1C' C1C' C2C' C3C' -179.9(12) . . . . ?
C6C' C1C' C2C' C3C' 0.4(11) . . . . ?
O1C' C1C' C2C' N1C' 1.6(15) . . . . ?
C6C' C1C' C2C' N1C' -178.2(15) . . . . ?
N1C' C2C' C3C' C4C' 176.7(15) . . . . ?
C1C' C2C' C3C' C4C' -1.8(10) . . . . ?
C2C' C3C' C4C' C5C' 4(2) . . . . ?
C2C' C3C' C4C' C7C' 177.5(11) . . . . ?
C3C' C4C' C5C' C6C' -4(3) . . . . ?
C7C' C4C' C5C' C6C' -178.0(17) . . . . ?
C4C' C5C' C6C' C1C' 3(3) . . . . ?
O1C' C1C' C6C' C5C' 179.4(18) . . . . ?
C2C' C1C' C6C' C5C' -1(2) . . . . ?
C5C' C4C' C7C' N2C' 174(3) . . . . ?
C3C' C4C' C7C' N2C' 0(2) . . . . ?
C5C' C4C' C7C' N3C' -5(3) . . . . ?
C3C' C4C' C7C' N3C' -179(2) . . . . ?
N2C' C8C' C9C' N3C' 0(3) . . . . ?
N3C' C7C' N2C' C8C' 0(2) . . . . ?
C4C' C7C' N2C' C8C' -180.0(14) . . . . ?
C9C' C8C' N2C' C7C' 0(2) . . . . ?
N2C' C7C' N3C' C9C' 1(2) . . . . ?
C4C' C7C' N3C' C9C' -179.8(15) . . . . ?
C8C' C9C' N3C' C7C' -1(3) . . . . ?

_refine_diff_density_max         0.545
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.076

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
