# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_c1
_database_code_depnum_ccdc_archive 'CCDC 2306291'
loop_
_audit_author_name
_audit_author_address
'Chris Hebert Franco'
;Instituto Superior Tecnico, Universidade de Lisboa
Portugal
;
_audit_update_record             
;
2025-01-27 deposited with the CCDC.	2025-05-07 downloaded from the CCDC.
;
_audit_creation_date             2023-06-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
chris.franco@tecnico.ulisboa.pt
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H12 N4 O2, H2 O'
_chemical_formula_sum            'C8 H14 N4 O3'
_chemical_formula_weight         214.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C2 H2 N2 O2 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.0489(9)
_cell_length_b                   8.2275(8)
_cell_length_c                   8.8795(9)
_cell_angle_alpha                65.458(10)
_cell_angle_beta                 78.475(9)
_cell_angle_gamma                73.773(10)
_cell_volume                     511.22(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1817
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9080
_cell_measurement_theta_min      3.3390
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3641
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         2.533
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0303
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  19.00   1.00    7.50    --   13.76  77.00 -90.00   27
  2  ω     -7.00  23.00   1.00    7.50    --   13.76  77.00  30.00   30
  3  ω     -3.00  25.00   1.00    7.50    --   13.76  77.00 150.00   28
  4  ω    -40.00  42.00   1.00    7.50    --  -15.95  77.00  30.00   82
  5  ω    -37.00  41.00   1.00    7.50    --  -15.95  77.00 150.00   78
  6  ω    -41.00  41.00   1.00    7.50    --  -15.95  77.00 -90.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0216125000
_diffrn_orient_matrix_UB_12      -0.0550228000
_diffrn_orient_matrix_UB_13      -0.0479613000
_diffrn_orient_matrix_UB_21      0.0006681000
_diffrn_orient_matrix_UB_22      0.0795332000
_diffrn_orient_matrix_UB_23      -0.0739660000
_diffrn_orient_matrix_UB_31      0.0896336000
_diffrn_orient_matrix_UB_32      -0.0093562000
_diffrn_orient_matrix_UB_33      0.0034169000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1617
_reflns_number_total             2074
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2074
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0507
_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)+(0.0829P)²+0.0423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1494
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: O3(0.5) H3A(0.5) H3B(0.5) O3A(0.5) H3AA(0.5) H3AB(0.5)
3.a Free rotating group:
 O3(H3A,H3B), O3A(H3AA,H3AB)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C5(H5)
3.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O2 O 0.33292(16) 1.00148(16) 0.17039(16) 0.0445(4) Uani 1 1 d . . . . .
O1 O 0.67058(16) 0.51858(19) 0.05547(16) 0.0480(4) Uani 1 1 d . . . . .
N4 N 0.10494(17) 0.29873(19) 0.76156(17) 0.0334(4) Uani 1 1 d . . . . .
N1 N 0.49605(17) 0.75663(19) 0.11452(16) 0.0329(4) Uani 1 1 d . . . . .
H1 H 0.542464 0.831443 0.026740 0.040 Uiso 1 1 calc R U . . .
N2 N 0.47402(17) 0.45639(18) 0.28439(16) 0.0320(4) Uani 1 1 d . . . . .
N3 N 0.27751(17) 0.38344(19) 0.51528(17) 0.0329(4) Uani 1 1 d . . . . .
C4 C 0.34188(19) 0.5204(2) 0.38697(19) 0.0285(4) Uani 1 1 d . . . . .
C1 C 0.5542(2) 0.5732(2) 0.1452(2) 0.0329(4) Uani 1 1 d . . . . .
C2 C 0.3698(2) 0.8316(2) 0.2120(2) 0.0317(4) Uani 1 1 d . . . . .
C3 C 0.2917(2) 0.7054(2) 0.3506(2) 0.0316(4) Uani 1 1 d . . . . .
H3 H 0.203843 0.748465 0.419366 0.038 Uiso 1 1 calc R U . . .
C5 C 0.1686(2) 0.4241(2) 0.6315(2) 0.0309(4) Uani 1 1 d . . . . .
H5 H 0.135036 0.545470 0.621927 0.037 Uiso 1 1 calc R U . . .
C6 C -0.0119(2) 0.3455(3) 0.8922(2) 0.0457(5) Uani 1 1 d . . . . .
H6A H 0.045246 0.292236 0.992382 0.068 Uiso 1 1 calc R U . . .
H6B H -0.114525 0.299034 0.912127 0.068 Uiso 1 1 calc R U . . .
H6C H -0.043746 0.476299 0.858541 0.068 Uiso 1 1 calc R U . . .
C8 C 0.5351(3) 0.2599(3) 0.3182(3) 0.0469(5) Uani 1 1 d . . . . .
H8A H 0.527144 0.191548 0.436202 0.070 Uiso 1 1 calc R U . . .
H8B H 0.653802 0.236232 0.272662 0.070 Uiso 1 1 calc R U . . .
H8C H 0.464273 0.223566 0.267970 0.070 Uiso 1 1 calc R U . . .
C7 C 0.1568(3) 0.1069(3) 0.7853(3) 0.0497(5) Uani 1 1 d . . . . .
H7A H 0.056924 0.064198 0.786433 0.075 Uiso 1 1 calc R U . . .
H7B H 0.206846 0.037030 0.889148 0.075 Uiso 1 1 calc R U . . .
H7C H 0.241095 0.092328 0.695990 0.075 Uiso 1 1 calc R U . . .
O3 O 0.0355(8) 1.1445(7) 0.3706(9) 0.0750(15) Uani 0.5 1 d G . P A 1
H3A H 0.009548 1.044922 0.440754 0.113 Uiso 0.5 1 d G U P A 1
H3B H 0.124254 1.111094 0.311333 0.113 Uiso 0.5 1 d G U P A 1
O3A O 0.1140(6) 1.1612(8) 0.3873(7) 0.0629(13) Uani 0.5 1 d G . P B 2
H3AA H 0.174966 1.112441 0.320690 0.094 Uiso 0.5 1 d G U P B 2
H3AB H 0.024005 1.228067 0.338133 0.094 Uiso 0.5 1 d G U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.249(2) . ?
O1 C1 1.216(2) . ?
N4 C5 1.315(2) . ?
N4 C6 1.453(2) . ?
N4 C7 1.449(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.373(2) . ?
N1 C2 1.380(2) . ?
N2 C4 1.392(2) . ?
N2 C1 1.381(2) . ?
N2 C8 1.468(2) . ?
N3 C4 1.364(2) . ?
N3 C5 1.306(2) . ?
C4 C3 1.373(2) . ?
C2 C3 1.408(2) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
O3 H3A 0.8501 . ?
O3 H3B 0.8500 . ?
O3A H3AA 0.8501 . ?
O3A H3AB 0.8500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N4 C6 121.28(15) . . ?
C5 N4 C7 121.31(14) . . ?
C7 N4 C6 117.31(14) . . ?
C1 N1 H1 117.1 . . ?
C1 N1 C2 125.81(14) . . ?
C2 N1 H1 117.1 . . ?
C4 N2 C8 121.50(14) . . ?
C1 N2 C4 122.17(14) . . ?
C1 N2 C8 116.32(13) . . ?
C5 N3 C4 118.47(14) . . ?
N3 C4 N2 112.97(14) . . ?
N3 C4 C3 128.04(14) . . ?
C3 C4 N2 118.99(15) . . ?
O1 C1 N1 121.42(16) . . ?
O1 C1 N2 122.69(16) . . ?
N1 C1 N2 115.88(14) . . ?
O2 C2 N1 118.66(15) . . ?
O2 C2 C3 125.92(15) . . ?
N1 C2 C3 115.40(15) . . ?
C4 C3 C2 121.69(15) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
N4 C5 H5 119.0 . . ?
N3 C5 N4 122.01(15) . . ?
N3 C5 H5 119.0 . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
N4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
N4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H3A O3 H3B 104.5 . . ?
H3AA O3A H3AB 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C2 C3 C4 -179.60(16) . . . . ?
N1 C2 C3 C4 1.4(2) . . . . ?
N2 C4 C3 C2 0.4(2) . . . . ?
N3 C4 C3 C2 -179.50(15) . . . . ?
C4 N2 C1 O1 179.45(14) . . . . ?
C4 N2 C1 N1 0.3(2) . . . . ?
C4 N3 C5 N4 -177.97(14) . . . . ?
C1 N1 C2 O2 178.36(15) . . . . ?
C1 N1 C2 C3 -2.6(2) . . . . ?
C1 N2 C4 N3 178.58(13) . . . . ?
C1 N2 C4 C3 -1.3(2) . . . . ?
C2 N1 C1 O1 -177.40(15) . . . . ?
C2 N1 C1 N2 1.8(2) . . . . ?
C5 N3 C4 N2 171.53(13) . . . . ?
C5 N3 C4 C3 -8.6(2) . . . . ?
C6 N4 C5 N3 178.08(15) . . . . ?
C8 N2 C4 N3 -1.0(2) . . . . ?
C8 N2 C4 C3 179.09(15) . . . . ?
C8 N2 C1 O1 -0.9(2) . . . . ?
C8 N2 C1 N1 179.94(14) . . . . ?
C7 N4 C5 N3 1.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.495
_oxdiff_exptl_absorpt_empirical_full_min 0.578

# start Validation Reply Form
_vrf_PLAT420_c1                  
;
PROBLEM: D-H Bond Without Acceptor O3A --H3AB . Please Check 
RESPONSE: The hydrogen atoms in the molecules of the solvent are related
to level B alerts. Because of the disorder of water molecules and their low
scattering power, hydrogen atoms are difficult to locate correctly
from X-ray data.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_c3
_database_code_depnum_ccdc_archive 'CCDC 2306292'
loop_
_audit_author_name
_audit_author_address
'Chris Hebert Franco'
;Instituto Superior Tecnico, Universidade de Lisboa
Portugal
;
_audit_update_record             
;
2025-01-27 deposited with the CCDC.	2025-05-07 downloaded from the CCDC.
;
_audit_creation_date             2023-11-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
chris.franco@tecnico.ulisboa.pt
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H8 N2 O4, 2(H2 O)'
_chemical_formula_sum            'C7 H12 N2 O6'
_chemical_formula_weight         220.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   5.1105(6)
_cell_length_b                   7.7802(9)
_cell_length_c                   13.1733(13)
_cell_angle_alpha                77.211(9)
_cell_angle_beta                 89.735(9)
_cell_angle_gamma                76.363(10)
_cell_volume                     495.76(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1899
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.5460
_cell_measurement_theta_min      2.8530
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.071
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.042
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3756
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.766
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0303
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  42.00   1.00   14.82    --   13.76  77.00-120.00   51
  2  ω     15.00  50.00   1.00   14.82    --   13.76 -99.00 150.00   35
  3  ω     -3.00  24.00   1.00   14.82    --   13.76  77.00   0.00   27
  4  ω    -71.00  53.00   1.00   14.82    --  -15.95   0.00-180.00  124
  5  ω    -86.00 -57.00   1.00   14.82    --  -15.95 178.00-180.00   29
  6  ω    -83.00  -3.00   1.00   14.82    --  -15.95 -38.00 -30.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1206527000
_diffrn_orient_matrix_UB_12      0.0631292000
_diffrn_orient_matrix_UB_13      0.0063035000
_diffrn_orient_matrix_UB_21      -0.0767528000
_diffrn_orient_matrix_UB_22      -0.0556671000
_diffrn_orient_matrix_UB_23      -0.0154975000
_diffrn_orient_matrix_UB_31      -0.0006097000
_diffrn_orient_matrix_UB_32      -0.0468314000
_diffrn_orient_matrix_UB_33      0.0526911000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1665
_reflns_number_total             2026
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2026
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.073
_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)+(0.0772P)²+0.2394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1627
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O5-H5D = O5-H5E
 0.85 with sigma of 0.02
 O6-H6C = O6-H6D
 0.85 with sigma of 0.02
 H5D-H5E
 1.34 with sigma of 0.04
 H6C-H6D
 1.34 with sigma of 0.04
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4A)
3.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
3.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O2 O 0.1880(3) 0.6504(2) 1.01585(11) 0.0446(5) Uani 1 1 d . . . . .
O1 O 0.4903(3) 0.4805(3) 0.72014(12) 0.0473(5) Uani 1 1 d . . . . .
O5 O 0.3899(4) 1.1417(3) 0.65431(15) 0.0546(5) Uani 1 1 d D . . . .
H5D H 0.264(6) 1.178(5) 0.696(2) 0.082 Uiso 1 1 d D U . . .
H5E H 0.319(7) 1.074(4) 0.626(3) 0.082 Uiso 1 1 d D U . . .
N1 N 0.3322(4) 0.5681(3) 0.86709(13) 0.0357(5) Uani 1 1 d . . . . .
H1 H 0.478354 0.503163 0.901168 0.043 Uiso 1 1 calc R U . . .
O6 O 0.0089(4) 0.2500(3) 0.79201(15) 0.0595(6) Uani 1 1 d D . . . .
H6C H -0.143(5) 0.322(5) 0.768(2) 0.089 Uiso 1 1 d D U . . .
H6D H 0.015(8) 0.252(5) 0.8575(15) 0.089 Uiso 1 1 d D U . . .
N2 N 0.0729(4) 0.6679(3) 0.71257(13) 0.0338(4) Uani 1 1 d . . . . .
O4 O 0.2603(4) 0.7003(3) 0.44906(12) 0.0526(5) Uani 1 1 d . . . . .
H4 H 0.358215 0.755940 0.412991 0.079 Uiso 1 1 calc R U . . .
O3 O 0.3258(4) 0.8659(3) 0.55972(15) 0.0615(6) Uani 1 1 d . . . . .
C2 C 0.1427(4) 0.6639(3) 0.92199(16) 0.0332(5) Uani 1 1 d . . . . .
C1 C 0.3104(4) 0.5662(3) 0.76382(16) 0.0336(5) Uani 1 1 d . . . . .
C4 C -0.1196(4) 0.7716(3) 0.76171(17) 0.0350(5) Uani 1 1 d . . . . .
H4A H -0.274387 0.842932 0.723030 0.042 Uiso 1 1 calc R U . . .
C7 C 0.2235(5) 0.7546(3) 0.53562(16) 0.0363(5) Uani 1 1 d . . . . .
C3 C -0.0960(4) 0.7753(3) 0.86259(16) 0.0344(5) Uani 1 1 d . . . . .
C6 C 0.0353(5) 0.6621(3) 0.60369(16) 0.0393(6) Uani 1 1 d . . . . .
H6A H -0.149727 0.721628 0.579501 0.047 Uiso 1 1 calc R U . . .
H6B H 0.068250 0.536618 0.598083 0.047 Uiso 1 1 calc R U . . .
C5 C -0.3050(5) 0.8907(4) 0.91573(19) 0.0483(6) Uani 1 1 d . . . . .
H5A H -0.370639 0.814439 0.972654 0.073 Uiso 1 1 calc R U . . .
H5B H -0.451910 0.957577 0.866777 0.073 Uiso 1 1 calc R U . . .
H5C H -0.226143 0.973979 0.941709 0.073 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.236(2) . ?
O1 C1 1.224(3) . ?
O5 H5D 0.883(18) . ?
O5 H5E 0.856(18) . ?
N1 H1 0.8600 . ?
N1 C2 1.382(3) . ?
N1 C1 1.369(3) . ?
O6 H6C 0.855(18) . ?
O6 H6D 0.867(18) . ?
N2 C1 1.368(3) . ?
N2 C4 1.374(3) . ?
N2 C6 1.460(3) . ?
O4 H4 0.8200 . ?
O4 C7 1.299(3) . ?
O3 C7 1.209(3) . ?
C2 C3 1.436(3) . ?
C4 H4A 0.9300 . ?
C4 C3 1.342(3) . ?
C7 C6 1.510(3) . ?
C3 C5 1.502(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

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
H5D O5 H5E 102(3) . . ?
C2 N1 H1 116.8 . . ?
C1 N1 H1 116.8 . . ?
C1 N1 C2 126.47(18) . . ?
H6C O6 H6D 104(3) . . ?
C1 N2 C4 121.15(18) . . ?
C1 N2 C6 117.01(18) . . ?
C4 N2 C6 121.83(18) . . ?
C7 O4 H4 109.5 . . ?
O2 C2 N1 119.42(19) . . ?
O2 C2 C3 124.95(19) . . ?
N1 C2 C3 115.63(18) . . ?
O1 C1 N1 122.6(2) . . ?
O1 C1 N2 122.25(19) . . ?
N1 C1 N2 115.20(18) . . ?
N2 C4 H4A 118.3 . . ?
C3 C4 N2 123.4(2) . . ?
C3 C4 H4A 118.3 . . ?
O4 C7 C6 111.9(2) . . ?
O3 C7 O4 124.7(2) . . ?
O3 C7 C6 123.4(2) . . ?
C2 C3 C5 118.69(19) . . ?
C4 C3 C2 117.98(19) . . ?
C4 C3 C5 123.3(2) . . ?
N2 C6 C7 111.30(19) . . ?
N2 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 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
O5 H5D O6 0.883(18) 1.885(18) 2.768(3) 177(3) 1_565 yes
O5 H5E O3 0.856(18) 1.99(2) 2.790(3) 155(3) . yes
N1 H1 O2 0.86 2.00 2.862(2) 178.3 2_667 yes
O6 H6C O1 0.855(18) 2.004(19) 2.858(3) 176(4) 1_455 yes
O4 H4 O5 0.82 1.80 2.614(3) 172.2 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
O2 C2 C3 C4 -178.1(2) . . . . ?
O2 C2 C3 C5 2.4(3) . . . . ?
N1 C2 C3 C4 2.6(3) . . . . ?
N1 C2 C3 C5 -177.0(2) . . . . ?
N2 C4 C3 C2 -0.4(3) . . . . ?
N2 C4 C3 C5 179.1(2) . . . . ?
O4 C7 C6 N2 158.4(2) . . . . ?
O3 C7 C6 N2 -21.8(3) . . . . ?
C2 N1 C1 O1 178.3(2) . . . . ?
C2 N1 C1 N2 -1.3(3) . . . . ?
C1 N1 C2 O2 178.8(2) . . . . ?
C1 N1 C2 C3 -1.7(3) . . . . ?
C1 N2 C4 C3 -2.9(3) . . . . ?
C1 N2 C6 C7 -68.7(3) . . . . ?
C4 N2 C1 O1 -176.0(2) . . . . ?
C4 N2 C1 N1 3.6(3) . . . . ?
C4 N2 C6 C7 110.8(2) . . . . ?
C6 N2 C1 O1 3.5(3) . . . . ?
C6 N2 C1 N1 -176.85(19) . . . . ?
C6 N2 C4 C3 177.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.672
_oxdiff_exptl_absorpt_empirical_full_min 0.700
