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

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

data_cmpd5
_database_code_depnum_ccdc_archive 'CCDC 2169308'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_audit_creation_date             2022-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'6-(4,6-diamino-1,3,5-triazin-2-yl)pyridin-2(1H)-one methanol solvate'
_chemical_formula_moiety         'C8 H8 N6 O, C H4 O'
_chemical_formula_sum            'C9 H12 N6 O2'
_chemical_formula_weight         236.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1197(6)
_cell_length_b                   8.3630(6)
_cell_length_c                   8.3902(5)
_cell_angle_alpha                94.326(5)
_cell_angle_beta                 99.044(5)
_cell_angle_gamma                110.439(5)
_cell_volume                     521.98(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1000
_cell_measurement_temperature    100
_cell_measurement_theta_max      69.823
_cell_measurement_theta_min      5.393
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.848
_exptl_absorpt_coefficient_mu    0.944
_exptl_absorpt_correction_T_max  0.2238
_exptl_absorpt_correction_T_min  0.1041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1566 before and 0.0551 after correction.
The Ratio of minimum to maximum transmission is 0.4651.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_recrystallization_method 'crystallsed from MeOH'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7245
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.006
_diffrn_reflns_theta_min         5.392
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_ambient_temperature_device_make 'Oxford Crysostream 700'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Hampton Research Cryoloop'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1544
_reflns_number_total             1972
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         1972
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0746P)²+0.1667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1227
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2-H2A
 0.85 with sigma of 0.002
 N1-H1 \\sim N5-H5A \\sim N5-H5B \\sim N6-H6A \\sim N6-H6B
 with sigma of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0046(2) 0.32920(19) 0.22676(17) 0.0358(4) Uani 1 1 d . . . . .
O2 O 0.0866(2) -0.0015(2) 0.36051(18) 0.0387(4) Uani 1 1 d D . . . .
H2A H -0.0209(19) -0.071(4) 0.351(5) 0.085(13) Uiso 1 1 d D . . . .
N1 N 0.1938(2) 0.3651(2) 0.4688(2) 0.0312(4) Uani 1 1 d D . . . .
H1 H 0.158(3) 0.2487(17) 0.456(3) 0.039(7) Uiso 1 1 d D . . . .
N2 N 0.2961(2) 0.2130(2) 0.7289(2) 0.0319(4) Uani 1 1 d . . . . .
N3 N 0.5395(2) 0.2195(2) 0.9351(2) 0.0322(4) Uani 1 1 d . . . . .
N4 N 0.5542(2) 0.4718(2) 0.8116(2) 0.0316(4) Uani 1 1 d . . . . .
N5 N 0.2896(3) -0.0244(2) 0.8546(2) 0.0360(4) Uani 1 1 d D . . . .
H5A H 0.338(3) -0.083(3) 0.922(3) 0.048(8) Uiso 1 1 d D . . . .
H5B H 0.180(2) -0.091(3) 0.796(3) 0.052(8) Uiso 1 1 d D . . . .
N6 N 0.7839(2) 0.4729(2) 1.0101(2) 0.0336(4) Uani 1 1 d D . . . .
H6A H 0.844(3) 0.575(2) 0.979(3) 0.031(6) Uiso 1 1 d D . . . .
H6B H 0.835(3) 0.414(3) 1.074(3) 0.046(7) Uiso 1 1 d D . . . .
C1 C 0.1112(3) 0.4296(3) 0.3483(2) 0.0318(5) Uani 1 1 d . . . . .
C2 C 0.1548(3) 0.6127(3) 0.3734(2) 0.0342(5) Uani 1 1 d . . . . .
H2 H 0.096350 0.663795 0.297348 0.041 Uiso 1 1 calc R U . . .
C3 C 0.2781(3) 0.7139(3) 0.5041(3) 0.0357(5) Uani 1 1 d . . . . .
H3 H 0.306650 0.834960 0.517421 0.043 Uiso 1 1 calc R U . . .
C4 C 0.3642(3) 0.6402(3) 0.6205(2) 0.0342(5) Uani 1 1 d . . . . .
H4 H 0.452837 0.711023 0.710454 0.041 Uiso 1 1 calc R U . . .
C5 C 0.3181(3) 0.4666(3) 0.6014(2) 0.0313(4) Uani 1 1 d . . . . .
C6 C 0.3944(3) 0.3772(3) 0.7225(2) 0.0310(4) Uani 1 1 d . . . . .
C7 C 0.6220(3) 0.3842(3) 0.9177(2) 0.0307(4) Uani 1 1 d . . . . .
C8 C 0.3762(3) 0.1382(3) 0.8396(2) 0.0318(4) Uani 1 1 d . . . . .
C9 C 0.1464(3) -0.0054(3) 0.2087(3) 0.0416(5) Uani 1 1 d . . . . .
H9A H 0.051620 -0.091997 0.126546 0.062 Uiso 1 1 calc R U . . .
H9B H 0.253957 -0.034978 0.223344 0.062 Uiso 1 1 calc R U . . .
H9C H 0.174520 0.108147 0.172410 0.062 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
O1 C1 1.257(3) . ?
O2 H2A 0.851(2) . ?
O2 C9 1.435(3) . ?
N1 H1 0.906(13) . ?
N1 C1 1.373(3) . ?
N1 C5 1.372(3) . ?
N2 C6 1.336(3) . ?
N2 C8 1.364(3) . ?
N3 C7 1.335(3) . ?
N3 C8 1.348(3) . ?
N4 C6 1.326(3) . ?
N4 C7 1.363(3) . ?
N5 H5A 0.906(13) . ?
N5 H5B 0.906(13) . ?
N5 C8 1.321(3) . ?
N6 H6A 0.906(13) . ?
N6 H6B 0.906(13) . ?
N6 C7 1.338(3) . ?
C1 C2 1.436(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.358(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.414(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.356(3) . ?
C5 C6 1.489(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C9 O2 H2A 111(3) . . ?
C1 N1 H1 114.7(17) . . ?
C5 N1 H1 121.8(17) . . ?
C5 N1 C1 123.44(18) . . ?
C6 N2 C8 113.84(17) . . ?
C7 N3 C8 115.74(18) . . ?
C6 N4 C7 113.54(18) . . ?
H5A N5 H5B 113(3) . . ?
C8 N5 H5A 122.4(18) . . ?
C8 N5 H5B 124.7(19) . . ?
H6A N6 H6B 125(2) . . ?
C7 N6 H6A 115.2(16) . . ?
C7 N6 H6B 117.4(18) . . ?
O1 C1 N1 119.79(19) . . ?
O1 C1 C2 124.54(19) . . ?
N1 C1 C2 115.67(18) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.07(19) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C6 117.05(18) . . ?
C4 C5 N1 120.45(19) . . ?
C4 C5 C6 122.49(19) . . ?
N2 C6 C5 117.09(18) . . ?
N4 C6 N2 127.67(19) . . ?
N4 C6 C5 115.23(18) . . ?
N3 C7 N4 125.05(19) . . ?
N3 C7 N6 118.75(18) . . ?
N6 C7 N4 116.20(18) . . ?
N3 C8 N2 124.14(19) . . ?
N5 C8 N2 118.35(18) . . ?
N5 C8 N3 117.51(18) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2A N2 0.851(2) 2.099(11) 2.928(2) 165(4) 2_556 yes
N1 H1 O2 0.906(13) 2.027(15) 2.907(2) 164(2) . yes
N5 H5A N3 0.906(13) 2.087(13) 2.991(3) 176(3) 2_657 yes
N5 H5B O1 0.906(13) 2.00(2) 2.764(2) 141(3) 2_556 yes
N6 H6A O1 0.906(13) 2.307(19) 3.037(2) 137(2) 2_666 yes
N6 H6B O1 0.906(13) 2.071(15) 2.961(2) 167(2) 1_656 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -176.7(2) . . . . ?
N1 C1 C2 C3 3.7(3) . . . . ?
N1 C5 C6 N2 -24.0(3) . . . . ?
N1 C5 C6 N4 155.80(19) . . . . ?
C1 N1 C5 C4 0.8(3) . . . . ?
C1 N1 C5 C6 179.41(18) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C3 C4 C5 N1 1.9(3) . . . . ?
C3 C4 C5 C6 -176.6(2) . . . . ?
C4 C5 C6 N2 154.5(2) . . . . ?
C4 C5 C6 N4 -25.6(3) . . . . ?
C5 N1 C1 O1 176.84(19) . . . . ?
C5 N1 C1 C2 -3.5(3) . . . . ?
C6 N2 C8 N3 0.0(3) . . . . ?
C6 N2 C8 N5 -179.83(19) . . . . ?
C6 N4 C7 N3 -0.5(3) . . . . ?
C6 N4 C7 N6 179.50(18) . . . . ?
C7 N3 C8 N2 0.9(3) . . . . ?
C7 N3 C8 N5 -179.29(19) . . . . ?
C7 N4 C6 N2 1.6(3) . . . . ?
C7 N4 C6 C5 -178.22(17) . . . . ?
C8 N2 C6 N4 -1.4(3) . . . . ?
C8 N2 C6 C5 178.45(18) . . . . ?
C8 N3 C7 N4 -0.6(3) . . . . ?
C8 N3 C7 N6 179.38(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cmpd7
_database_code_depnum_ccdc_archive 'CCDC 2169311'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_audit_creation_date             2022-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I, C8 H9 N6 O'
_chemical_formula_sum            'C8 H9 I N6 O'
_chemical_formula_weight         332.11
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8788(3)
_cell_length_b                   8.8064(3)
_cell_length_c                   8.8494(3)
_cell_angle_alpha                115.810(1)
_cell_angle_beta                 99.266(2)
_cell_angle_gamma                97.192(2)
_cell_volume                     532.20(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5046
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.910
_cell_measurement_theta_min      5.721
_shelx_estimated_absorpt_T_max   0.650
_shelx_estimated_absorpt_T_min   0.452
_exptl_absorpt_coefficient_mu    23.588
_exptl_absorpt_correction_T_max  0.171059
_exptl_absorpt_correction_T_min  0.046858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1628 before and 0.0484 after correction.
 
For component 2:
 wR2(int) was 0.1726 before and 0.0521 after correction.
 The Ratio of minimum to maximum transmission is 0.23.

Final HKLF 4 output contains 19279 reflections, Rint = 0.0532
 (15507 with I > 3sig(I), Rint = 0.0511)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.072
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector 
distance was 4.0 cm, and the data collection was carried out in 512 x 512 
pixel mode. The initial unit cell parameters were determined by a 
least-squares fit of the angular setting of strong reflections, collected 
by a 180.0 degree scan in 180 frames over three different parts of 
the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2035
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.902
_diffrn_reflns_theta_min         5.720
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 700'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1999
_reflns_number_total             2035
_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       ?
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2013) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.652
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.261
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2035
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.143
_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)+(0.0974P)²+0.2887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1217
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.631(3)
 0.369(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C4(H4), C5(H5)
3.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N6(H6A,H6B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.73994(4) 0.06810(3) 0.88111(3) 0.01901(18) Uani 1 1 d . . . . .
O1 O 0.7328(5) 0.6372(5) 1.0163(5) 0.0211(8) Uani 1 1 d . . . . .
N1 N 0.5820(6) 0.3781(6) 0.7919(6) 0.0181(9) Uani 1 1 d . . . . .
H1 H 0.644727 0.325123 0.836724 0.022 Uiso 1 1 calc R U . . .
N2 N 0.2471(6) 0.7807(6) 0.6796(5) 0.0158(9) Uani 1 1 d . . . . .
H2 H 0.300905 0.834551 0.790204 0.019 Uiso 1 1 calc R U . . .
N3 N 0.0621(6) 0.7800(6) 0.4429(6) 0.0159(9) Uani 1 1 d . . . . .
N4 N 0.1723(6) 0.5282(6) 0.4170(6) 0.0170(9) Uani 1 1 d . . . . .
N5 N 0.1453(6) 1.0242(6) 0.7060(6) 0.0194(9) Uani 1 1 d . . . . .
H5A H 0.084187 1.078475 0.661634 0.023 Uiso 1 1 calc R U . . .
H5B H 0.203264 1.078177 0.815344 0.023 Uiso 1 1 calc R U . . .
N6 N -0.0220(6) 0.5221(6) 0.1923(6) 0.0180(9) Uani 1 1 d . . . . .
H6A H -0.088723 0.570274 0.144722 0.022 Uiso 1 1 calc R U . . .
H6B H -0.017557 0.413133 0.132303 0.022 Uiso 1 1 calc R U . . .
C1 C 0.6143(7) 0.5542(7) 0.8810(7) 0.0165(10) Uani 1 1 d . . . . .
C2 C 0.5004(7) 0.6330(7) 0.8053(6) 0.0162(10) Uani 1 1 d . . . . .
H2A H 0.513463 0.754965 0.861349 0.019 Uiso 1 1 calc R U . . .
C3 C 0.3742(7) 0.5340(7) 0.6543(7) 0.0162(10) Uani 1 1 d . . . . .
C4 C 0.3549(7) 0.3521(6) 0.5644(7) 0.0149(10) Uani 1 1 d . . . . .
H4 H 0.271858 0.284179 0.456338 0.018 Uiso 1 1 calc R U . . .
C5 C 0.4597(7) 0.2771(7) 0.6382(7) 0.0162(10) Uani 1 1 d . . . . .
H5 H 0.447585 0.155261 0.582837 0.019 Uiso 1 1 calc R U . . .
C6 C 0.2602(7) 0.6153(7) 0.5776(7) 0.0159(10) Uani 1 1 d . . . . .
C7 C 0.1499(7) 0.8616(7) 0.6083(7) 0.0175(10) Uani 1 1 d . . . . .
C8 C 0.0718(7) 0.6135(7) 0.3545(7) 0.0171(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.244(7) . ?
N1 H1 0.8800 . ?
N1 C1 1.365(7) . ?
N1 C5 1.371(7) . ?
N2 H2 0.8800 . ?
N2 C6 1.368(7) . ?
N2 C7 1.366(7) . ?
N3 C7 1.331(7) . ?
N3 C8 1.347(7) . ?
N4 C6 1.299(7) . ?
N4 C8 1.367(7) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C7 1.321(7) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C8 1.325(7) . ?
C1 C2 1.450(7) . ?
C2 H2A 0.9500 . ?
C2 C3 1.369(7) . ?
C3 C4 1.419(7) . ?
C3 C6 1.472(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.372(7) . ?
C5 H5 0.9500 . ?

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
C1 N1 H1 117.4 . . ?
C1 N1 C5 125.2(5) . . ?
C5 N1 H1 117.4 . . ?
C6 N2 H2 120.3 . . ?
C7 N2 H2 120.3 . . ?
C7 N2 C6 119.4(5) . . ?
C7 N3 C8 115.7(5) . . ?
C6 N4 C8 116.2(5) . . ?
H5A N5 H5B 120.0 . . ?
C7 N5 H5A 120.0 . . ?
C7 N5 H5B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C8 N6 H6A 120.0 . . ?
C8 N6 H6B 120.0 . . ?
O1 C1 N1 121.4(5) . . ?
O1 C1 C2 123.9(5) . . ?
N1 C1 C2 114.7(5) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 C1 120.9(5) . . ?
C3 C2 H2A 119.5 . . ?
C2 C3 C4 121.0(5) . . ?
C2 C3 C6 120.6(5) . . ?
C4 C3 C6 118.4(5) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.0(5) . . ?
C5 C4 H4 121.0 . . ?
N1 C5 C4 120.0(5) . . ?
N1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
N2 C6 C3 118.6(5) . . ?
N4 C6 N2 121.7(5) . . ?
N4 C6 C3 119.7(5) . . ?
N3 C7 N2 121.2(5) . . ?
N5 C7 N2 118.9(5) . . ?
N5 C7 N3 120.0(5) . . ?
N3 C8 N4 125.6(5) . . ?
N6 C8 N3 118.5(5) . . ?
N6 C8 N4 115.9(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5A N3 0.88 2.18 3.061(7) 178.4 2_576 yes
N5 H5B O1 0.88 2.22 2.828(6) 125.6 2_677 yes
N6 H6A O1 0.88 1.97 2.843(6) 169.7 1_454 yes
N6 H6B I1 0.88 3.02 3.736(4) 139.8 1_454 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 178.9(5) . . . . ?
N1 C1 C2 C3 -1.2(8) . . . . ?
C1 N1 C5 C4 -1.7(8) . . . . ?
C1 C2 C3 C4 -2.1(8) . . . . ?
C1 C2 C3 C6 -179.4(5) . . . . ?
C2 C3 C4 C5 3.6(8) . . . . ?
C2 C3 C6 N2 -18.0(8) . . . . ?
C2 C3 C6 N4 163.3(5) . . . . ?
C3 C4 C5 N1 -1.8(8) . . . . ?
C4 C3 C6 N2 164.6(5) . . . . ?
C4 C3 C6 N4 -14.1(8) . . . . ?
C5 N1 C1 O1 -177.0(5) . . . . ?
C5 N1 C1 C2 3.2(8) . . . . ?
C6 N2 C7 N3 2.6(8) . . . . ?
C6 N2 C7 N5 -176.7(5) . . . . ?
C6 N4 C8 N3 2.6(8) . . . . ?
C6 N4 C8 N6 -177.9(5) . . . . ?
C6 C3 C4 C5 -179.0(5) . . . . ?
C7 N2 C6 N4 -5.0(8) . . . . ?
C7 N2 C6 C3 176.4(5) . . . . ?
C7 N3 C8 N4 -4.8(8) . . . . ?
C7 N3 C8 N6 175.7(5) . . . . ?
C8 N3 C7 N2 2.0(7) . . . . ?
C8 N3 C7 N5 -178.8(5) . . . . ?
C8 N4 C6 N2 2.5(8) . . . . ?
C8 N4 C6 C3 -179.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.631(3)
2 0.369(3)

####################################################################### 
# 
# 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_cmpd2
_database_code_depnum_ccdc_archive 'CCDC 2169309'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_audit_creation_date             2022-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H14 N6 O2, H2 O'
_chemical_formula_sum            'C11 H16 N6 O3'
_chemical_formula_weight         280.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0907(5)
_cell_length_b                   8.6941(5)
_cell_length_c                   10.2522(7)
_cell_angle_alpha                72.622(3)
_cell_angle_beta                 88.326(3)
_cell_angle_gamma                68.746(3)
_cell_volume                     638.89(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4113
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.302
_cell_measurement_theta_min      4.537
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1274 before and 0.0407 after correction. 
The Ratio of minimum to maximum transmission is 0.9274. 
The λ/2 correction factor is Not present.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_recrystallization_method 'crystallised in H2O'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12441
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.502
_diffrn_reflns_theta_min         4.537
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 700'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2124
_reflns_number_total             2444
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0742P)²+0.2171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1256
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.88882(14) 0.77162(13) 0.25864(11) 0.0221(3) Uani 1 1 d . . . . .
O2 O 0.85320(15) 1.21535(14) 0.15418(12) 0.0256(3) Uani 1 1 d . . . . .
N1 N 0.73986(17) 0.69811(16) 0.44864(14) 0.0212(3) Uani 1 1 d . . . . .
N2 N 0.61035(16) 0.32008(16) 0.74344(13) 0.0188(3) Uani 1 1 d . . . . .
N3 N 0.58642(17) 0.04068(16) 0.81885(13) 0.0200(3) Uani 1 1 d . . . . .
N4 N 0.71064(17) 0.13000(16) 0.60713(13) 0.0198(3) Uani 1 1 d . . . . .
N5 N 0.49087(18) 0.22901(17) 0.94508(14) 0.0219(3) Uani 1 1 d . . . . .
H5A H 0.483(3) 0.320(3) 0.965(2) 0.034(5) Uiso 1 1 d . . . . .
H5B H 0.467(2) 0.152(3) 1.005(2) 0.020(4) Uiso 1 1 d . . . . .
N6 N 0.67718(19) -0.13293(18) 0.67979(15) 0.0257(3) Uani 1 1 d . . . . .
H6A H 0.637(3) -0.205(3) 0.735(2) 0.022(4) Uiso 1 1 d . . . . .
H6B H 0.711(3) -0.146(3) 0.601(2) 0.034(6) Uiso 1 1 d . . . . .
C1 C 0.83518(19) 0.6544(2) 0.34932(16) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.8855(2) 0.4905(2) 0.33060(15) 0.0215(3) Uani 1 1 d . . . . .
H2 H 0.952299 0.465805 0.256611 0.026 Uiso 1 1 calc R U . . .
C3 C 0.8359(2) 0.36706(19) 0.42182(16) 0.0213(3) Uani 1 1 d . . . . .
H3 H 0.868104 0.254869 0.411981 0.026 Uiso 1 1 calc R U . . .
C4 C 0.73708(19) 0.40792(19) 0.53001(15) 0.0189(3) Uani 1 1 d . . . . .
C5 C 0.6920(2) 0.5752(2) 0.53703(15) 0.0204(3) Uani 1 1 d . . . . .
H5 H 0.622969 0.604779 0.608703 0.024 Uiso 1 1 calc R U . . .
C6 C 0.68286(18) 0.27792(19) 0.63341(15) 0.0186(3) Uani 1 1 d . . . . .
C7 C 0.56425(19) 0.19575(19) 0.83332(16) 0.0191(3) Uani 1 1 d . . . . .
C8 C 0.65693(19) 0.01637(19) 0.70253(16) 0.0204(3) Uani 1 1 d . . . . .
C9 C 0.8388(2) 0.94115(19) 0.27587(16) 0.0221(3) Uani 1 1 d . . . . .
H9A H 0.897205 0.934092 0.362110 0.027 Uiso 1 1 calc R U . . .
H9B H 0.708122 0.995390 0.276705 0.027 Uiso 1 1 calc R U . . .
C10 C 0.9038(2) 1.04165(19) 0.15225(15) 0.0208(3) Uani 1 1 d . . . . .
H10A H 1.034997 0.987961 0.154719 0.025 Uiso 1 1 calc R U . . .
H10B H 0.850926 1.039964 0.067074 0.025 Uiso 1 1 calc R U . . .
C11 C 0.9131(2) 1.3157(2) 0.03977(18) 0.0293(4) Uani 1 1 d . . . . .
H11A H 0.871183 1.306304 -0.045212 0.044 Uiso 1 1 calc R U . . .
H11B H 1.043515 1.272194 0.048380 0.044 Uiso 1 1 calc R U . . .
H11C H 0.865756 1.437472 0.037517 0.044 Uiso 1 1 calc R U . . .
O3 O 0.51572(17) 0.61575(15) 0.83564(12) 0.0253(3) Uani 1 1 d . . . . .
H3A H 0.541(3) 0.535(3) 0.801(2) 0.032(5) Uiso 1 1 d . . . . .
H3B H 0.402(4) 0.667(3) 0.828(3) 0.049(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3500(18) . ?
O1 C9 1.4444(17) . ?
O2 C10 1.4204(18) . ?
O2 C11 1.4260(19) . ?
N1 C1 1.323(2) . ?
N1 C5 1.347(2) . ?
N2 C6 1.343(2) . ?
N2 C7 1.354(2) . ?
N3 C7 1.3470(19) . ?
N3 C8 1.348(2) . ?
N4 C6 1.331(2) . ?
N4 C8 1.353(2) . ?
N5 H5A 0.85(2) . ?
N5 H5B 0.84(2) . ?
N5 C7 1.335(2) . ?
N6 H6A 0.86(2) . ?
N6 H6B 0.87(2) . ?
N6 C8 1.338(2) . ?
C1 C2 1.404(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.371(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.405(2) . ?
C4 C5 1.389(2) . ?
C4 C6 1.487(2) . ?
C5 H5 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.510(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O3 H3A 0.83(2) . ?
O3 H3B 0.86(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C9 117.56(12) . . ?
C10 O2 C11 110.87(12) . . ?
C1 N1 C5 116.93(13) . . ?
C6 N2 C7 114.39(12) . . ?
C7 N3 C8 114.50(13) . . ?
C6 N4 C8 114.45(13) . . ?
H5A N5 H5B 117.2(19) . . ?
C7 N5 H5A 122.2(15) . . ?
C7 N5 H5B 119.8(13) . . ?
H6A N6 H6B 120.7(18) . . ?
C8 N6 H6A 119.4(13) . . ?
C8 N6 H6B 118.7(14) . . ?
O1 C1 C2 116.54(13) . . ?
N1 C1 O1 119.56(14) . . ?
N1 C1 C2 123.90(14) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.29(14) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.40(14) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C6 121.63(13) . . ?
C5 C4 C3 117.32(14) . . ?
C5 C4 C6 121.05(14) . . ?
N1 C5 C4 124.14(14) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
N2 C6 C4 117.55(13) . . ?
N4 C6 N2 126.16(14) . . ?
N4 C6 C4 116.28(13) . . ?
N3 C7 N2 125.10(14) . . ?
N5 C7 N2 117.66(13) . . ?
N5 C7 N3 117.23(14) . . ?
N3 C8 N4 125.35(13) . . ?
N6 C8 N3 117.50(14) . . ?
N6 C8 N4 117.15(14) . . ?
O1 C9 H9A 111.1 . . ?
O1 C9 H9B 111.1 . . ?
O1 C9 C10 103.51(12) . . ?
H9A C9 H9B 109.0 . . ?
C10 C9 H9A 111.1 . . ?
C10 C9 H9B 111.1 . . ?
O2 C10 C9 108.66(12) . . ?
O2 C10 H10A 110.0 . . ?
O2 C10 H10B 110.0 . . ?
C9 C10 H10A 110.0 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 108.3 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H3A O3 H3B 109(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5A O3 0.85(2) 2.27(2) 2.9380(18) 134.8(19) 2_667 yes
N5 H5B N3 0.84(2) 2.22(2) 3.0547(19) 173.5(18) 2_657 yes
N6 H6A O3 0.86(2) 2.13(2) 2.9826(18) 168.5(18) 1_545 yes
N6 H6B N1 0.87(2) 2.32(2) 3.0822(19) 147.3(18) 1_545 yes
O3 H3A N2 0.83(2) 2.01(2) 2.8408(17) 173(2) . yes
O3 H3B O2 0.86(3) 1.97(3) 2.8235(17) 169(2) 2_676 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.03(13) . . . . ?
O1 C9 C10 O2 176.95(11) . . . . ?
N1 C1 C2 C3 -1.2(2) . . . . ?
C1 O1 C9 C10 -174.88(11) . . . . ?
C1 N1 C5 C4 0.3(2) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C2 C3 C4 C6 -178.78(13) . . . . ?
C3 C4 C5 N1 -1.3(2) . . . . ?
C3 C4 C6 N2 171.05(13) . . . . ?
C3 C4 C6 N4 -9.2(2) . . . . ?
C5 N1 C1 O1 -179.22(12) . . . . ?
C5 N1 C1 C2 1.0(2) . . . . ?
C5 C4 C6 N2 -8.8(2) . . . . ?
C5 C4 C6 N4 170.94(13) . . . . ?
C6 N2 C7 N3 0.1(2) . . . . ?
C6 N2 C7 N5 -179.83(13) . . . . ?
C6 N4 C8 N3 -2.4(2) . . . . ?
C6 N4 C8 N6 178.29(13) . . . . ?
C6 C4 C5 N1 178.54(13) . . . . ?
C7 N2 C6 N4 0.3(2) . . . . ?
C7 N2 C6 C4 -179.97(12) . . . . ?
C7 N3 C8 N4 2.7(2) . . . . ?
C7 N3 C8 N6 -177.93(13) . . . . ?
C8 N3 C7 N2 -1.5(2) . . . . ?
C8 N3 C7 N5 178.43(13) . . . . ?
C8 N4 C6 N2 0.7(2) . . . . ?
C8 N4 C6 C4 -179.00(12) . . . . ?
C9 O1 C1 N1 0.3(2) . . . . ?
C9 O1 C1 C2 -179.94(12) . . . . ?
C11 O2 C10 C9 179.49(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cmpd4
_database_code_depnum_ccdc_archive 'CCDC 2169312'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_audit_creation_date             2022-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H14 N6 O2'
_chemical_formula_sum            'C11 H14 N6 O2'
_chemical_formula_weight         262.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9536(4)
_cell_length_b                   10.7657(4)
_cell_length_c                   13.1905(5)
_cell_angle_alpha                80.790(2)
_cell_angle_beta                 76.962(2)
_cell_angle_gamma                63.772(2)
_cell_volume                     1232.30(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9624
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.56
_cell_measurement_theta_min      4.59
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.840
_exptl_absorpt_coefficient_mu    0.858
_exptl_absorpt_correction_T_max  0.1137
_exptl_absorpt_correction_T_min  0.0175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1529 before and 0.0575 after correction.
The Ratio of minimum to maximum transmission is 0.1539.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chunk
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30916
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.752
_diffrn_reflns_theta_min         3.447
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 700'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4239
_reflns_number_total             4722
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         4722
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0757P)²+0.2093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1259
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N5A-H5AB \\sim N5A-H5AA \\sim N6A-H6AA \\sim N6A-H6AB \\sim N5B-H5BA \\sim
N5B-H5BB \\sim N6B-H6BB ~
 N6B-H6BA
 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C10A(H10A,H10B), C9B(H9BA,H9BB), C10B(H10C,H10D)
3.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C4A(H4A), C2B(H2B), C3B(H3B), C4B(H4B)
3.c Idealised Me refined as rotating group:
 C11A(H11A,H11B,H11C), C11B(H11D,H11E,H11F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.49411(11) 1.13120(10) 0.72919(7) 0.0368(2) Uani 1 1 d . . . . .
O2A O 0.58974(11) 1.33660(10) 0.78608(8) 0.0400(2) Uani 1 1 d . . . . .
N1A N 0.63913(14) 1.02813(12) 0.57754(9) 0.0379(3) Uani 1 1 d . . . . .
N2A N 0.44197(13) 0.93301(12) 0.89941(9) 0.0351(3) Uani 1 1 d . . . . .
N3A N 0.25834(14) 0.84678(12) 0.98907(9) 0.0381(3) Uani 1 1 d . . . . .
N4A N 0.34630(13) 0.82757(11) 0.80563(9) 0.0346(3) Uani 1 1 d . . . . .
N5A N 0.35821(16) 0.94207(14) 1.07747(10) 0.0425(3) Uani 1 1 d D . . . .
H5AA H 0.321(2) 0.902(2) 1.1341(13) 0.060(6) Uiso 1 1 d D . . . .
H5AB H 0.423(2) 0.977(2) 1.0837(17) 0.066(6) Uiso 1 1 d D . . . .
N6A N 0.16363(15) 0.75437(13) 0.89317(10) 0.0388(3) Uani 1 1 d D . . . .
H6AA H 0.161(2) 0.7290(18) 0.8324(11) 0.042(4) Uiso 1 1 d D . . . .
H6AB H 0.113(2) 0.734(2) 0.9540(12) 0.056(5) Uiso 1 1 d D . . . .
C1A C 0.55949(15) 1.01923(14) 0.67139(11) 0.0346(3) Uani 1 1 d . . . . .
C2A C 0.70896(17) 0.91549(15) 0.52159(12) 0.0405(3) Uani 1 1 d . . . . .
H2A H 0.766970 0.921995 0.454717 0.049 Uiso 1 1 calc R U . . .
C3A C 0.70041(16) 0.79091(15) 0.55665(12) 0.0393(3) Uani 1 1 d . . . . .
H3A H 0.753905 0.712087 0.516412 0.047 Uiso 1 1 calc R U . . .
C4A C 0.61058(16) 0.78516(14) 0.65304(11) 0.0376(3) Uani 1 1 d . . . . .
H4A H 0.599189 0.701948 0.678068 0.045 Uiso 1 1 calc R U . . .
C5A C 0.53709(15) 0.89913(14) 0.71347(11) 0.0344(3) Uani 1 1 d . . . . .
C6A C 0.43454(15) 0.88839(13) 0.81307(11) 0.0341(3) Uani 1 1 d . . . . .
C7A C 0.35206(16) 0.90626(14) 0.98688(11) 0.0362(3) Uani 1 1 d . . . . .
C8A C 0.25752(16) 0.81108(14) 0.89698(11) 0.0353(3) Uani 1 1 d . . . . .
C9A C 0.48393(17) 1.26307(14) 0.67515(11) 0.0386(3) Uani 1 1 d . . . . .
H9AA H 0.401500 1.300768 0.633347 0.046 Uiso 1 1 calc R U . . .
H9AB H 0.580813 1.249805 0.627406 0.046 Uiso 1 1 calc R U . . .
C10A C 0.45164(16) 1.36181(14) 0.75468(12) 0.0397(3) Uani 1 1 d . . . . .
H10A H 0.404948 1.458531 0.724686 0.048 Uiso 1 1 calc R U . . .
H10B H 0.379155 1.349226 0.815940 0.048 Uiso 1 1 calc R U . . .
C11A C 0.56691(18) 1.43132(16) 0.85824(13) 0.0455(4) Uani 1 1 d . . . . .
H11A H 0.517727 1.526501 0.828243 0.068 Uiso 1 1 calc R U . . .
H11B H 0.665279 1.415472 0.873677 0.068 Uiso 1 1 calc R U . . .
H11C H 0.501918 1.417547 0.922745 0.068 Uiso 1 1 calc R U . . .
O1B O 0.09137(11) 0.33974(10) 0.76294(8) 0.0388(2) Uani 1 1 d . . . . .
O2B O 0.03809(12) 0.11636(11) 0.69153(8) 0.0444(3) Uani 1 1 d . . . . .
N1B N -0.08207(13) 0.42324(12) 0.91281(9) 0.0373(3) Uani 1 1 d . . . . .
N2B N 0.06581(14) 0.56377(12) 0.59205(9) 0.0366(3) Uani 1 1 d . . . . .
N3B N 0.22227(14) 0.67916(12) 0.50299(9) 0.0381(3) Uani 1 1 d . . . . .
N4B N 0.14568(13) 0.68032(12) 0.68853(9) 0.0349(3) Uani 1 1 d . . . . .
N5B N 0.14080(16) 0.56843(13) 0.41321(10) 0.0417(3) Uani 1 1 d D . . . .
H5BA H 0.176(2) 0.6092(18) 0.3565(12) 0.047(5) Uiso 1 1 d D . . . .
H5BB H 0.080(2) 0.530(2) 0.4070(16) 0.059(6) Uiso 1 1 d D . . . .
N6B N 0.30246(15) 0.78247(13) 0.60088(10) 0.0404(3) Uani 1 1 d D . . . .
H6BA H 0.340(2) 0.8171(18) 0.5410(11) 0.048(5) Uiso 1 1 d D . . . .
H6BB H 0.310(2) 0.8014(19) 0.6631(11) 0.048(5) Uiso 1 1 d D . . . .
C1B C -0.00703(15) 0.44669(14) 0.82062(11) 0.0347(3) Uani 1 1 d . . . . .
C2B C -0.17772(16) 0.53304(15) 0.96832(12) 0.0391(3) Uani 1 1 d . . . . .
H2B H -0.230901 0.516375 1.034649 0.047 Uiso 1 1 calc R U . . .
C3B C -0.20324(16) 0.66849(15) 0.93469(12) 0.0398(3) Uani 1 1 d . . . . .
H3B H -0.273678 0.743442 0.975597 0.048 Uiso 1 1 calc R U . . .
C4B C -0.12172(16) 0.69107(14) 0.83843(11) 0.0379(3) Uani 1 1 d . . . . .
H4B H -0.134908 0.782795 0.813296 0.046 Uiso 1 1 calc R U . . .
C5B C -0.02170(15) 0.58072(14) 0.77923(11) 0.0345(3) Uani 1 1 d . . . . .
C6B C 0.07106(15) 0.60753(13) 0.67917(11) 0.0345(3) Uani 1 1 d . . . . .
C7B C 0.14335(16) 0.60540(14) 0.50424(11) 0.0362(3) Uani 1 1 d . . . . .
C8B C 0.22285(16) 0.71251(14) 0.59632(11) 0.0361(3) Uani 1 1 d . . . . .
C9B C 0.12198(17) 0.20052(14) 0.80955(12) 0.0401(3) Uani 1 1 d . . . . .
H9BA H 0.120857 0.198969 0.884981 0.048 Uiso 1 1 calc R U . . .
H9BB H 0.225185 0.136236 0.777784 0.048 Uiso 1 1 calc R U . . .
C10B C 0.00900(17) 0.14916(14) 0.79610(11) 0.0394(3) Uani 1 1 d . . . . .
H10C H 0.018560 0.065743 0.843660 0.047 Uiso 1 1 calc R U . . .
H10D H -0.095798 0.221745 0.813421 0.047 Uiso 1 1 calc R U . . .
C11B C -0.05729(19) 0.05833(16) 0.67432(13) 0.0461(4) Uani 1 1 d . . . . .
H11D H -0.031479 0.035018 0.601504 0.069 Uiso 1 1 calc R U . . .
H11E H -0.163769 0.125776 0.689091 0.069 Uiso 1 1 calc R U . . .
H11F H -0.042543 -0.025899 0.720469 0.069 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
O1A C1A 1.3545(17) . ?
O1A C9A 1.4544(15) . ?
O2A C10A 1.4233(17) . ?
O2A C11A 1.4163(18) . ?
N1A C1A 1.3253(18) . ?
N1A C2A 1.3447(19) . ?
N2A C6A 1.3333(19) . ?
N2A C7A 1.3677(18) . ?
N3A C7A 1.3382(19) . ?
N3A C8A 1.3341(19) . ?
N4A C6A 1.3333(19) . ?
N4A C8A 1.3617(18) . ?
N5A H5AA 0.892(14) . ?
N5A H5AB 0.896(14) . ?
N5A C7A 1.335(2) . ?
N6A H6AA 0.896(13) . ?
N6A H6AB 0.898(13) . ?
N6A C8A 1.3356(19) . ?
C1A C5A 1.4138(18) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.380(2) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.390(2) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.390(2) . ?
C5A C6A 1.4940(19) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.496(2) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
O1B C1B 1.3458(17) . ?
O1B C9B 1.4503(15) . ?
O2B C10B 1.4129(18) . ?
O2B C11B 1.4177(19) . ?
N1B C1B 1.3262(18) . ?
N1B C2B 1.3445(19) . ?
N2B C6B 1.3295(19) . ?
N2B C7B 1.3691(18) . ?
N3B C7B 1.3376(19) . ?
N3B C8B 1.3383(19) . ?
N4B C6B 1.3296(19) . ?
N4B C8B 1.3669(18) . ?
N5B H5BA 0.888(13) . ?
N5B H5BB 0.894(14) . ?
N5B C7B 1.333(2) . ?
N6B H6BA 0.894(13) . ?
N6B H6BB 0.902(13) . ?
N6B C8B 1.3275(19) . ?
C1B C5B 1.4139(18) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.380(2) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.393(2) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.383(2) . ?
C5B C6B 1.4971(19) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C9B C10B 1.508(2) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 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
C1A O1A C9A 117.00(11) . . ?
C11A O2A C10A 111.90(11) . . ?
C1A N1A C2A 118.71(12) . . ?
C6A N2A C7A 113.79(12) . . ?
C8A N3A C7A 115.11(12) . . ?
C6A N4A C8A 114.61(12) . . ?
H5AA N5A H5AB 119(2) . . ?
C7A N5A H5AA 114.9(14) . . ?
C7A N5A H5AB 123.0(14) . . ?
H6AA N6A H6AB 121.9(18) . . ?
C8A N6A H6AA 120.1(12) . . ?
C8A N6A H6AB 117.5(13) . . ?
O1A C1A C5A 118.30(12) . . ?
N1A C1A O1A 118.57(12) . . ?
N1A C1A C5A 123.12(13) . . ?
N1A C2A H2A 118.4 . . ?
N1A C2A C3A 123.15(13) . . ?
C3A C2A H2A 118.4 . . ?
C2A C3A H3A 121.3 . . ?
C2A C3A C4A 117.46(13) . . ?
C4A C3A H3A 121.3 . . ?
C3A C4A H4A 119.4 . . ?
C3A C4A C5A 121.10(13) . . ?
C5A C4A H4A 119.4 . . ?
C1A C5A C6A 125.45(13) . . ?
C4A C5A C1A 116.33(13) . . ?
C4A C5A C6A 118.11(12) . . ?
N2A C6A C5A 119.61(12) . . ?
N4A C6A N2A 126.33(13) . . ?
N4A C6A C5A 114.00(12) . . ?
N3A C7A N2A 125.25(13) . . ?
N5A C7A N2A 117.52(13) . . ?
N5A C7A N3A 117.24(13) . . ?
N3A C8A N4A 124.81(13) . . ?
N3A C8A N6A 118.21(13) . . ?
N6A C8A N4A 116.97(13) . . ?
O1A C9A H9AA 110.0 . . ?
O1A C9A H9AB 110.0 . . ?
O1A C9A C10A 108.48(11) . . ?
H9AA C9A H9AB 108.4 . . ?
C10A C9A H9AA 110.0 . . ?
C10A C9A H9AB 110.0 . . ?
O2A C10A C9A 109.45(12) . . ?
O2A C10A H10A 109.8 . . ?
O2A C10A H10B 109.8 . . ?
C9A C10A H10A 109.8 . . ?
C9A C10A H10B 109.8 . . ?
H10A C10A H10B 108.2 . . ?
O2A C11A H11A 109.5 . . ?
O2A C11A H11B 109.5 . . ?
O2A C11A H11C 109.5 . . ?
H11A C11A H11B 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C1B O1B C9B 117.63(11) . . ?
C10B O2B C11B 112.25(11) . . ?
C1B N1B C2B 117.93(12) . . ?
C6B N2B C7B 113.54(12) . . ?
C7B N3B C8B 115.47(12) . . ?
C6B N4B C8B 114.15(12) . . ?
H5BA N5B H5BB 118.3(18) . . ?
C7B N5B H5BA 116.1(12) . . ?
C7B N5B H5BB 122.4(13) . . ?
H6BA N6B H6BB 121.5(17) . . ?
C8B N6B H6BA 118.0(12) . . ?
C8B N6B H6BB 120.2(12) . . ?
O1B C1B C5B 116.90(12) . . ?
N1B C1B O1B 119.97(12) . . ?
N1B C1B C5B 123.11(13) . . ?
N1B C2B H2B 118.1 . . ?
N1B C2B C3B 123.89(13) . . ?
C3B C2B H2B 118.1 . . ?
C2B C3B H3B 121.3 . . ?
C2B C3B C4B 117.43(14) . . ?
C4B C3B H3B 121.3 . . ?
C3B C4B H4B 119.8 . . ?
C5B C4B C3B 120.38(13) . . ?
C5B C4B H4B 119.8 . . ?
C1B C5B C6B 123.62(13) . . ?
C4B C5B C1B 117.24(13) . . ?
C4B C5B C6B 119.03(12) . . ?
N2B C6B N4B 127.25(13) . . ?
N2B C6B C5B 118.71(12) . . ?
N4B C6B C5B 113.96(12) . . ?
N3B C7B N2B 125.03(13) . . ?
N5B C7B N2B 117.31(13) . . ?
N5B C7B N3B 117.66(13) . . ?
N3B C8B N4B 124.48(13) . . ?
N6B C8B N3B 118.54(13) . . ?
N6B C8B N4B 116.98(13) . . ?
O1B C9B H9BA 108.9 . . ?
O1B C9B H9BB 108.9 . . ?
O1B C9B C10B 113.38(12) . . ?
H9BA C9B H9BB 107.7 . . ?
C10B C9B H9BA 108.9 . . ?
C10B C9B H9BB 108.9 . . ?
O2B C10B C9B 108.89(12) . . ?
O2B C10B H10C 109.9 . . ?
O2B C10B H10D 109.9 . . ?
C9B C10B H10C 109.9 . . ?
C9B C10B H10D 109.9 . . ?
H10C C10B H10D 108.3 . . ?
O2B C11B H11D 109.5 . . ?
O2B C11B H11E 109.5 . . ?
O2B C11B H11F 109.5 . . ?
H11D C11B H11E 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5A H5AA O2A 0.892(14) 2.457(18) 3.1347(16) 133.1(17) 2_677 yes
N5A H5AB N2A 0.896(14) 2.042(14) 2.9372(18) 176(2) 2_677 yes
N6A H6AA N4B 0.896(13) 2.103(13) 2.9976(18) 176.8(17) . yes
N6A H6AB N1B 0.898(13) 2.303(15) 3.1199(16) 151.2(17) 2_567 yes
N5B H5BB N2B 0.894(14) 2.099(14) 2.9904(18) 174.5(19) 2_566 yes
N6B H6BA N1A 0.894(13) 2.142(14) 2.9882(17) 157.7(16) 2_676 yes
N6B H6BB N4A 0.902(13) 2.078(13) 2.9764(18) 174.3(17) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A C1A C5A C4A -177.84(12) . . . . ?
O1A C1A C5A C6A 6.2(2) . . . . ?
O1A C9A C10A O2A 81.64(14) . . . . ?
N1A C1A C5A C4A 3.3(2) . . . . ?
N1A C1A C5A C6A -172.65(13) . . . . ?
N1A C2A C3A C4A 2.2(2) . . . . ?
C1A O1A C9A C10A -163.89(11) . . . . ?
C1A N1A C2A C3A 0.8(2) . . . . ?
C1A C5A C6A N2A -48.97(19) . . . . ?
C1A C5A C6A N4A 133.57(14) . . . . ?
C2A N1A C1A O1A 177.51(12) . . . . ?
C2A N1A C1A C5A -3.7(2) . . . . ?
C2A C3A C4A C5A -2.5(2) . . . . ?
C3A C4A C5A C1A -0.1(2) . . . . ?
C3A C4A C5A C6A 176.17(13) . . . . ?
C4A C5A C6A N2A 135.09(13) . . . . ?
C4A C5A C6A N4A -42.37(17) . . . . ?
C6A N2A C7A N3A -2.8(2) . . . . ?
C6A N2A C7A N5A 177.05(12) . . . . ?
C6A N4A C8A N3A -2.20(19) . . . . ?
C6A N4A C8A N6A 178.07(12) . . . . ?
C7A N2A C6A N4A 2.6(2) . . . . ?
C7A N2A C6A C5A -174.56(11) . . . . ?
C7A N3A C8A N4A 1.9(2) . . . . ?
C7A N3A C8A N6A -178.34(12) . . . . ?
C8A N3A C7A N2A 0.8(2) . . . . ?
C8A N3A C7A N5A -179.13(13) . . . . ?
C8A N4A C6A N2A -0.3(2) . . . . ?
C8A N4A C6A C5A 177.00(11) . . . . ?
C9A O1A C1A N1A 14.79(17) . . . . ?
C9A O1A C1A C5A -164.07(12) . . . . ?
C11A O2A C10A C9A 177.47(11) . . . . ?
O1B C1B C5B C4B -179.50(12) . . . . ?
O1B C1B C5B C6B -3.2(2) . . . . ?
O1B C9B C10B O2B 73.96(15) . . . . ?
N1B C1B C5B C4B -1.1(2) . . . . ?
N1B C1B C5B C6B 175.13(13) . . . . ?
N1B C2B C3B C4B -1.5(2) . . . . ?
C1B O1B C9B C10B 85.95(16) . . . . ?
C1B N1B C2B C3B 0.5(2) . . . . ?
C1B C5B C6B N2B 57.98(19) . . . . ?
C1B C5B C6B N4B -124.97(14) . . . . ?
C2B N1B C1B O1B 179.16(12) . . . . ?
C2B N1B C1B C5B 0.8(2) . . . . ?
C2B C3B C4B C5B 1.2(2) . . . . ?
C3B C4B C5B C1B 0.1(2) . . . . ?
C3B C4B C5B C6B -176.36(13) . . . . ?
C4B C5B C6B N2B -125.81(14) . . . . ?
C4B C5B C6B N4B 51.24(17) . . . . ?
C6B N2B C7B N3B 2.1(2) . . . . ?
C6B N2B C7B N5B -178.53(12) . . . . ?
C6B N4B C8B N3B 1.95(19) . . . . ?
C6B N4B C8B N6B -178.52(12) . . . . ?
C7B N2B C6B N4B -2.5(2) . . . . ?
C7B N2B C6B C5B 174.13(11) . . . . ?
C7B N3B C8B N4B -2.3(2) . . . . ?
C7B N3B C8B N6B 178.21(13) . . . . ?
C8B N3B C7B N2B 0.1(2) . . . . ?
C8B N3B C7B N5B -179.29(12) . . . . ?
C8B N4B C6B N2B 0.6(2) . . . . ?
C8B N4B C6B C5B -176.11(11) . . . . ?
C9B O1B C1B N1B -5.85(19) . . . . ?
C9B O1B C1B C5B 172.56(12) . . . . ?
C11B O2B C10B C9B 176.03(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cmpd3
_database_code_depnum_ccdc_archive 'CCDC 2169310'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_audit_creation_date             2022-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C11 H14 N6 O2), 3(H2 O)'
_chemical_formula_sum            'C22 H34 N12 O7'
_chemical_formula_weight         578.61
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.8893(1)
_cell_length_b                   18.4452(2)
_cell_length_c                   12.5023(1)
_cell_angle_alpha                90
_cell_angle_beta                 93.4284(4)
_cell_angle_gamma                90
_cell_volume                     2736.85(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.385
_cell_measurement_theta_min      4.430
_shelx_estimated_absorpt_T_max   0.891
_shelx_estimated_absorpt_T_min   0.798
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1021 before and 0.0318 after correction.
The Ratio of minimum to maximum transmission is 0.9055.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32901
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.378
_diffrn_reflns_theta_min         4.430
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 700'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Hampton Research Cryoloop'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2607
_reflns_number_total             2666
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2013) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2013) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2666
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.068
_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)+(0.0606P)²+1.7593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.0998
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N5-H5A \\sim N5-H5B \\sim N6-H6A \\sim N6-H6B
 with sigma of 0.02
 O3-H3A \\sim O4-H4A \\sim O4-H4B
 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.84734(6) 0.55494(4) 0.45331(6) 0.0183(2) Uani 1 1 d . . . . .
O2 O 1.06845(7) 0.68712(5) 0.45820(7) 0.0270(2) Uani 1 1 d . . . . .
N1 N 0.83522(7) 0.50472(5) 0.62177(7) 0.0163(2) Uani 1 1 d . . . . .
N2 N 0.49594(7) 0.40342(5) 0.40948(7) 0.0147(2) Uani 1 1 d . . . . .
N3 N 0.34157(7) 0.32623(5) 0.44976(7) 0.0165(2) Uani 1 1 d . . . . .
N4 N 0.48114(8) 0.35907(5) 0.58740(7) 0.0182(2) Uani 1 1 d . . . . .
N5 N 0.35726(7) 0.37334(5) 0.28121(7) 0.0170(2) Uani 1 1 d D . . . .
H5A H 0.3942(11) 0.3968(7) 0.2336(10) 0.020(3) Uiso 1 1 d D . . . .
H5B H 0.2941(11) 0.3513(7) 0.2601(11) 0.022(3) Uiso 1 1 d D . . . .
N6 N 0.33717(8) 0.28119(6) 0.62115(8) 0.0217(2) Uani 1 1 d D . . . .
H6A H 0.3723(11) 0.2733(8) 0.6840(10) 0.021(3) Uiso 1 1 d D . . . .
H6B H 0.2817(11) 0.2511(8) 0.5993(11) 0.025(4) Uiso 1 1 d D . . . .
C1 C 0.79316(9) 0.51205(6) 0.52203(8) 0.0149(2) Uani 1 1 d . . . . .
C2 C 0.69456(9) 0.47803(6) 0.48098(8) 0.0156(2) Uani 1 1 d . . . . .
H2 H 0.668268 0.484307 0.408315 0.019 Uiso 1 1 calc R U . . .
C3 C 0.77675(9) 0.46284(6) 0.68785(8) 0.0184(2) Uani 1 1 d . . . . .
H3 H 0.805257 0.457513 0.760038 0.022 Uiso 1 1 calc R U . . .
C4 C 0.67861(9) 0.42762(6) 0.65644(8) 0.0180(2) Uani 1 1 d . . . . .
H4 H 0.640025 0.398982 0.705697 0.022 Uiso 1 1 calc R U . . .
C5 C 0.63671(9) 0.43501(6) 0.54964(8) 0.0152(2) Uani 1 1 d . . . . .
C6 C 0.53034(9) 0.39686(5) 0.51269(8) 0.0147(2) Uani 1 1 d . . . . .
C7 C 0.39831(8) 0.36756(5) 0.38265(8) 0.0148(2) Uani 1 1 d . . . . .
C8 C 0.38747(9) 0.32293(6) 0.55091(8) 0.0168(2) Uani 1 1 d . . . . .
C9 C 0.93730(9) 0.59882(6) 0.50013(8) 0.0170(2) Uani 1 1 d . . . . .
H9A H 0.999118 0.567786 0.530667 0.020 Uiso 1 1 calc R U . . .
H9B H 0.909711 0.629482 0.558047 0.020 Uiso 1 1 calc R U . . .
C10 C 0.97832(9) 0.64548(6) 0.41127(8) 0.0188(2) Uani 1 1 d . . . . .
H10A H 1.004576 0.614944 0.352596 0.023 Uiso 1 1 calc R U . . .
H10B H 0.917181 0.677474 0.381835 0.023 Uiso 1 1 calc R U . . .
C11 C 1.12030(10) 0.73100(7) 0.38197(10) 0.0252(3) Uani 1 1 d . . . . .
H11A H 1.159285 0.700022 0.332365 0.038 Uiso 1 1 calc R U . . .
H11B H 1.174757 0.763611 0.419080 0.038 Uiso 1 1 calc R U . . .
H11C H 1.062648 0.759678 0.341813 0.038 Uiso 1 1 calc R U . . .
O3 O 1.000000 0.57741(6) 0.750000 0.0202(2) Uani 1 2 d DS T P . .
H3A H 0.9552(14) 0.5505(9) 0.7080(13) 0.044(5) Uiso 1 1 d D . . . .
O4 O 1.13952(7) 0.68728(5) 0.68504(7) 0.0232(2) Uani 1 1 d D . . . .
H4A H 1.1209(15) 0.6937(10) 0.6172(12) 0.044(5) Uiso 1 1 d D . . . .
H4B H 1.0946(14) 0.6529(9) 0.7022(13) 0.038(4) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3584(13) . ?
O1 C9 1.4377(12) . ?
O2 C10 1.4168(13) . ?
O2 C11 1.4190(13) . ?
N1 C1 1.3224(14) . ?
N1 C3 1.3533(14) . ?
N2 C6 1.3356(13) . ?
N2 C7 1.3605(14) . ?
N3 C7 1.3445(14) . ?
N3 C8 1.3483(14) . ?
N4 C6 1.3288(14) . ?
N4 C8 1.3534(14) . ?
N5 H5A 0.876(12) . ?
N5 H5B 0.881(12) . ?
N5 C7 1.3357(14) . ?
N6 H6A 0.879(12) . ?
N6 H6B 0.892(12) . ?
N6 C8 1.3358(14) . ?
C1 C2 1.3998(15) . ?
C2 H2 0.9500 . ?
C2 C5 1.3821(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3722(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.4035(15) . ?
C5 C6 1.4960(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5092(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O3 H3A 0.879(14) . ?
O3 H3A 0.879(14) 2_756 ?
O4 H4A 0.872(15) . ?
O4 H4B 0.864(14) . ?

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
C1 O1 C9 116.08(8) . . ?
C10 O2 C11 112.29(8) . . ?
C1 N1 C3 117.06(9) . . ?
C6 N2 C7 113.68(9) . . ?
C7 N3 C8 114.89(9) . . ?
C6 N4 C8 114.16(9) . . ?
H5A N5 H5B 118.6(13) . . ?
C7 N5 H5A 121.0(9) . . ?
C7 N5 H5B 120.3(9) . . ?
H6A N6 H6B 118.3(13) . . ?
C8 N6 H6A 118.3(9) . . ?
C8 N6 H6B 120.6(9) . . ?
O1 C1 C2 116.59(9) . . ?
N1 C1 O1 119.28(9) . . ?
N1 C1 C2 124.13(10) . . ?
C1 C2 H2 121.1 . . ?
C5 C2 C1 117.81(9) . . ?
C5 C2 H2 121.1 . . ?
N1 C3 H3 118.2 . . ?
N1 C3 C4 123.69(10) . . ?
C4 C3 H3 118.2 . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.27(10) . . ?
C5 C4 H4 120.9 . . ?
C2 C5 C4 119.02(10) . . ?
C2 C5 C6 121.41(9) . . ?
C4 C5 C6 119.57(9) . . ?
N2 C6 C5 117.39(9) . . ?
N4 C6 N2 127.18(9) . . ?
N4 C6 C5 115.42(9) . . ?
N3 C7 N2 125.05(10) . . ?
N5 C7 N2 116.95(9) . . ?
N5 C7 N3 117.99(9) . . ?
N3 C8 N4 124.93(10) . . ?
N6 C8 N3 118.07(10) . . ?
N6 C8 N4 117.00(10) . . ?
O1 C9 H9A 110.4 . . ?
O1 C9 H9B 110.4 . . ?
O1 C9 C10 106.65(8) . . ?
H9A C9 H9B 108.6 . . ?
C10 C9 H9A 110.4 . . ?
C10 C9 H9B 110.4 . . ?
O2 C10 C9 105.90(8) . . ?
O2 C10 H10A 110.6 . . ?
O2 C10 H10B 110.6 . . ?
C9 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H3A O3 H3A 111(2) . 2_756 ?
H4A O4 H4B 102.5(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5A N2 0.876(12) 2.280(12) 3.0880(12) 153.4(12) 2_655 yes
N5 H5B O4 0.881(12) 2.135(12) 3.0041(12) 169.1(13) 6_465 yes
N6 H6A O4 0.879(12) 2.291(13) 2.9780(13) 134.9(12) 4_646 yes
N6 H6B N3 0.892(12) 2.110(13) 3.0005(13) 175.9(14) 7_556 yes
O3 H3A N1 0.879(14) 1.930(14) 2.7983(10) 169.1(17) . yes
O4 H4A O2 0.872(15) 2.051(15) 2.9105(12) 168.4(17) . yes
O4 H4B O3 0.864(14) 1.908(14) 2.7711(12) 176.0(16) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C5 -178.97(9) . . . . ?
O1 C9 C10 O2 -178.72(8) . . . . ?
N1 C1 C2 C5 1.07(16) . . . . ?
N1 C3 C4 C5 0.41(16) . . . . ?
C1 O1 C9 C10 -175.72(8) . . . . ?
C1 N1 C3 C4 0.83(16) . . . . ?
C1 C2 C5 C4 0.25(15) . . . . ?
C1 C2 C5 C6 179.75(9) . . . . ?
C2 C5 C6 N2 2.83(15) . . . . ?
C2 C5 C6 N4 -177.98(9) . . . . ?
C3 N1 C1 O1 178.45(9) . . . . ?
C3 N1 C1 C2 -1.59(15) . . . . ?
C3 C4 C5 C2 -0.93(15) . . . . ?
C3 C4 C5 C6 179.56(9) . . . . ?
C4 C5 C6 N2 -177.67(9) . . . . ?
C4 C5 C6 N4 1.52(14) . . . . ?
C6 N2 C7 N3 -2.79(14) . . . . ?
C6 N2 C7 N5 178.27(9) . . . . ?
C6 N4 C8 N3 -3.28(16) . . . . ?
C6 N4 C8 N6 176.94(9) . . . . ?
C7 N2 C6 N4 1.35(15) . . . . ?
C7 N2 C6 C5 -179.57(8) . . . . ?
C7 N3 C8 N4 2.05(15) . . . . ?
C7 N3 C8 N6 -178.17(9) . . . . ?
C8 N3 C7 N2 1.23(15) . . . . ?
C8 N3 C7 N5 -179.84(9) . . . . ?
C8 N4 C6 N2 1.45(16) . . . . ?
C8 N4 C6 C5 -177.65(9) . . . . ?
C9 O1 C1 N1 -9.94(14) . . . . ?
C9 O1 C1 C2 170.10(9) . . . . ?
C11 O2 C10 C9 176.53(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cmpd1
_database_code_depnum_ccdc_archive 'CCDC 2169313'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_audit_creation_date             2022-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H14 N6 O2, 2(H2 O)'
_chemical_formula_sum            'C11 H18 N6 O4'
_chemical_formula_weight         298.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.3831(5)
_cell_length_b                   6.8419(2)
_cell_length_c                   20.4027(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.9807(14)
_cell_angle_gamma                90
_cell_volume                     2808.77(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.188
_cell_measurement_theta_min      4.395
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.795
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1312 before and 0.0410 after correction.
The Ratio of minimum to maximum transmission is 0.9164.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear Colorless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            48198
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.474
_diffrn_reflns_theta_min         4.395
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 700'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Hampton Research Cryoloop'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2601
_reflns_number_total             2729
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2013) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2013) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.033
_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)+(0.0515P)²+2.4349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0916
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3-H3A \\sim O3-H3B \\sim O4-H4A \\sim O4-H4B
 with sigma of 0.02
 N5-H5A \\sim N5-H5B \\sim N6-H6A \\sim N6-H6B
 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47708(4) 0.77268(11) 0.42297(4) 0.01809(19) Uani 1 1 d . . . . .
O2 O 0.37387(4) 0.93148(12) 0.29093(4) 0.0215(2) Uani 1 1 d . . . . .
N1 N 0.55807(5) 0.53389(13) 0.45430(5) 0.0146(2) Uani 1 1 d . . . . .
N2 N 0.60215(5) 0.19489(13) 0.42195(5) 0.0149(2) Uani 1 1 d . . . . .
N3 N 0.68041(4) -0.06852(13) 0.45739(5) 0.0145(2) Uani 1 1 d . . . . .
N4 N 0.69567(4) 0.20122(13) 0.53839(5) 0.0141(2) Uani 1 1 d . . . . .
N5 N 0.58724(5) -0.06845(15) 0.34700(5) 0.0196(2) Uani 1 1 d D . . . .
H5A H 0.5966(8) -0.183(2) 0.3375(9) 0.030(4) Uiso 1 1 d D . . . .
H5B H 0.5542(7) -0.004(2) 0.3175(8) 0.029(4) Uiso 1 1 d D . . . .
N6 N 0.76967(5) -0.05397(14) 0.57007(5) 0.0167(2) Uani 1 1 d D . . . .
H6A H 0.7949(7) 0.008(2) 0.6091(7) 0.024(4) Uiso 1 1 d D . . . .
H6B H 0.7842(7) -0.161(2) 0.5594(8) 0.024(4) Uiso 1 1 d D . . . .
C1 C 0.53741(5) 0.70079(16) 0.46977(6) 0.0151(2) Uani 1 1 d . . . . .
C2 C 0.57342(6) 0.81247(16) 0.53262(6) 0.0170(2) Uani 1 1 d . . . . .
H2 H 0.555891 0.930204 0.541816 0.020 Uiso 1 1 calc R U . . .
C3 C 0.63503(6) 0.74461(17) 0.58028(6) 0.0169(2) Uani 1 1 d . . . . .
H3 H 0.661477 0.816646 0.623065 0.020 Uiso 1 1 calc R U . . .
C4 C 0.65851(5) 0.56924(16) 0.56546(6) 0.0158(2) Uani 1 1 d . . . . .
H4 H 0.701129 0.520522 0.597536 0.019 Uiso 1 1 calc R U . . .
C5 C 0.61826(5) 0.46820(16) 0.50298(6) 0.0133(2) Uani 1 1 d . . . . .
C6 C 0.64027(5) 0.27529(15) 0.48670(6) 0.0129(2) Uani 1 1 d . . . . .
C7 C 0.62455(5) 0.01973(16) 0.41058(6) 0.0144(2) Uani 1 1 d . . . . .
C8 C 0.71427(5) 0.02803(16) 0.52070(6) 0.0135(2) Uani 1 1 d . . . . .
C9 C 0.44088(5) 0.66070(17) 0.35766(6) 0.0182(2) Uani 1 1 d . . . . .
H9A H 0.438870 0.521880 0.370242 0.022 Uiso 1 1 calc R U . . .
H9B H 0.463541 0.668043 0.325551 0.022 Uiso 1 1 calc R U . . .
C10 C 0.37201(6) 0.74271(17) 0.31918(6) 0.0186(2) Uani 1 1 d . . . . .
H10A H 0.344191 0.654568 0.278827 0.022 Uiso 1 1 calc R U . . .
H10B H 0.351825 0.751562 0.353628 0.022 Uiso 1 1 calc R U . . .
C11 C 0.31065(7) 0.9903(2) 0.23717(7) 0.0312(3) Uani 1 1 d . . . . .
H11A H 0.295333 0.897785 0.196386 0.047 Uiso 1 1 calc R U . . .
H11B H 0.313947 1.121200 0.219556 0.047 Uiso 1 1 calc R U . . .
H11C H 0.278944 0.992471 0.258387 0.047 Uiso 1 1 calc R U . . .
O4 O 0.40445(5) 0.48956(13) 0.19179(5) 0.0242(2) Uani 1 1 d D . . . .
H4A H 0.4250(8) 0.417(2) 0.2299(8) 0.034(4) Uiso 1 1 d D . . . .
H4B H 0.4112(10) 0.434(3) 0.1584(10) 0.057(6) Uiso 1 1 d D . . . .
O3 O 0.46652(4) 0.21914(13) 0.30733(5) 0.0224(2) Uani 1 1 d D . . . .
H3A H 0.4432(8) 0.130(2) 0.3132(10) 0.045(5) Uiso 1 1 d D . . . .
H3B H 0.4982(8) 0.239(3) 0.3491(8) 0.046(5) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3593(13) . ?
O1 C9 1.4397(13) . ?
O2 C10 1.4223(14) . ?
O2 C11 1.4168(14) . ?
N1 C1 1.3211(14) . ?
N1 C5 1.3532(14) . ?
N2 C6 1.3373(14) . ?
N2 C7 1.3577(14) . ?
N3 C7 1.3392(14) . ?
N3 C8 1.3496(14) . ?
N4 C6 1.3270(14) . ?
N4 C8 1.3563(14) . ?
N5 H5A 0.856(13) . ?
N5 H5B 0.845(13) . ?
N5 C7 1.3398(15) . ?
N6 H6A 0.861(12) . ?
N6 H6B 0.864(13) . ?
N6 C8 1.3315(14) . ?
C1 C2 1.4044(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3740(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3952(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3814(15) . ?
C5 C6 1.4962(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.4991(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O4 H4A 0.865(13) . ?
O4 H4B 0.849(15) . ?
O3 H3A 0.847(14) . ?
O3 H3B 0.847(14) . ?

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
C1 O1 C9 116.15(8) . . ?
C11 O2 C10 112.02(10) . . ?
C1 N1 C5 116.86(10) . . ?
C6 N2 C7 114.10(9) . . ?
C7 N3 C8 114.79(9) . . ?
C6 N4 C8 114.27(9) . . ?
H5A N5 H5B 122.9(16) . . ?
C7 N5 H5A 121.4(11) . . ?
C7 N5 H5B 115.7(11) . . ?
H6A N6 H6B 118.9(14) . . ?
C8 N6 H6A 120.5(10) . . ?
C8 N6 H6B 119.6(10) . . ?
O1 C1 C2 116.15(10) . . ?
N1 C1 O1 119.27(10) . . ?
N1 C1 C2 124.58(10) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.32(10) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.59(10) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.37(10) . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 123.24(10) . . ?
N1 C5 C6 116.67(9) . . ?
C4 C5 C6 120.09(10) . . ?
N2 C6 C5 116.91(9) . . ?
N4 C6 N2 126.71(10) . . ?
N4 C6 C5 116.38(9) . . ?
N3 C7 N2 125.13(10) . . ?
N3 C7 N5 118.60(10) . . ?
N5 C7 N2 116.27(10) . . ?
N3 C8 N4 124.97(10) . . ?
N6 C8 N3 117.66(10) . . ?
N6 C8 N4 117.36(10) . . ?
O1 C9 H9A 110.0 . . ?
O1 C9 H9B 110.0 . . ?
O1 C9 C10 108.55(9) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.0 . . ?
C10 C9 H9B 110.0 . . ?
O2 C10 C9 110.26(9) . . ?
O2 C10 H10A 109.6 . . ?
O2 C10 H10B 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H4A O4 H4B 104.8(17) . . ?
H3A O3 H3B 105.7(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5A O4 0.856(13) 2.315(14) 3.1519(13) 165.8(14) 2_645 yes
N5 H5B O3 0.845(13) 2.422(14) 3.1484(13) 144.5(14) . yes
N6 H6A O4 0.861(12) 2.287(14) 2.9830(13) 138.0(13) 8_556 yes
N6 H6B N3 0.864(13) 2.102(13) 2.9635(14) 174.6(14) 7_646 yes
O4 H4A O3 0.865(13) 1.977(14) 2.8357(12) 171.7(16) . yes
O4 H4B N2 0.849(15) 2.243(16) 3.0282(12) 153.9(19) 2_655 yes
O3 H3A O2 0.847(14) 1.958(15) 2.7710(12) 160.6(18) 1_545 yes
O3 H3B N2 0.847(14) 2.165(16) 2.9143(13) 147.4(17) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.00(10) . . . . ?
O1 C9 C10 O2 68.71(12) . . . . ?
N1 C1 C2 C3 1.51(17) . . . . ?
N1 C5 C6 N2 7.07(14) . . . . ?
N1 C5 C6 N4 -172.65(9) . . . . ?
C1 O1 C9 C10 170.94(9) . . . . ?
C1 N1 C5 C4 -1.82(16) . . . . ?
C1 N1 C5 C6 177.66(9) . . . . ?
C1 C2 C3 C4 -1.14(16) . . . . ?
C2 C3 C4 C5 -0.54(16) . . . . ?
C3 C4 C5 N1 2.13(16) . . . . ?
C3 C4 C5 C6 -177.33(9) . . . . ?
C4 C5 C6 N2 -173.43(10) . . . . ?
C4 C5 C6 N4 6.85(14) . . . . ?
C5 N1 C1 O1 -179.53(9) . . . . ?
C5 N1 C1 C2 -0.05(16) . . . . ?
C6 N2 C7 N3 -1.72(15) . . . . ?
C6 N2 C7 N5 178.69(10) . . . . ?
C6 N4 C8 N3 -1.32(15) . . . . ?
C6 N4 C8 N6 179.69(9) . . . . ?
C7 N2 C6 N4 -0.01(16) . . . . ?
C7 N2 C6 C5 -179.70(9) . . . . ?
C7 N3 C8 N4 -0.14(15) . . . . ?
C7 N3 C8 N6 178.85(9) . . . . ?
C8 N3 C7 N2 1.77(15) . . . . ?
C8 N3 C7 N5 -178.64(10) . . . . ?
C8 N4 C6 N2 1.40(16) . . . . ?
C8 N4 C6 C5 -178.91(8) . . . . ?
C9 O1 C1 N1 -1.97(14) . . . . ?
C9 O1 C1 C2 178.51(9) . . . . ?
C11 O2 C10 C9 162.86(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
