# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_samp7046a
_database_code_depnum_ccdc_archive 'CCDC 2307422'
loop_
_audit_author_name
_audit_author_address
'Qi Li'
;Xiehe
China
;
_audit_update_record             
;
2024-12-01 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_audit_creation_date             2024-06-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H8 N4 O2, C4 H9 N O2'
_chemical_formula_sum            'C11 H17 N5 O4'
_chemical_formula_weight         283.29
_chemical_absolute_configuration rm
_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           9
_space_group_name_H-M_alt        'I 1 a 1'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   7.2517(2)
_cell_length_b                   21.6583(5)
_cell_length_c                   8.7412(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.434(3)
_cell_angle_gamma                90
_cell_volume                     1268.99(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9844
_cell_measurement_temperature    301.09(10)
_cell_measurement_theta_max      74.7620
_cell_measurement_theta_min      4.0440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.971
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.59a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       blocked
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0820
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10579
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.109
_diffrn_reflns_theta_min         4.082
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.09(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  27.00   0.50    0.05    --  -46.40  38.00 -60.00  134
  2  ω    -23.00  29.00   0.50    0.05    --  -46.40  19.00 -30.00  104
  3  ω    -23.00  29.00   0.50    0.05    --  -46.40  19.00 -90.00  104
  4  ω    -23.00  29.00   0.50    0.05    --  -46.40  19.00-150.00  104
  5  ω    -68.00 -30.00   0.50    0.05    -- -103.00  61.00-150.00   76
  6  ω    -68.00 -30.00   0.50    0.05    -- -103.00  61.00 -90.00   76
  7  ω    -68.00 -30.00   0.50    0.05    -- -103.00  61.00 -60.00   76
  8  ω   -102.00 -30.00   0.50    0.05    -- -103.00  77.00 -90.00  144
  9  ω    -68.00 -30.00   0.50    0.05    -- -103.00  61.00  30.00   76
 10  ω   -102.00 -30.00   0.50    0.05    -- -103.00  77.00  60.00  144
 11  ω   -102.00 -30.00   0.50    0.05    -- -103.00  77.00 120.00  144
 12  ω    -73.00  26.00   0.50    0.05    --  -46.40  85.00 -31.00  198
 13  ω   -118.00 -31.00   0.50    0.05    --  -46.40 -57.00-150.00  174
 14  ω   -118.00 -24.00   0.50    0.05    --  -46.40 -77.00-180.00  188
 15  ω   -118.00 -31.00   0.50    0.05    --  -46.40 -57.00 -90.00  174
 16  ω   -118.00 -24.00   0.50    0.05    --  -46.40 -77.00   0.00  188
 17  ω   -118.00 -31.00   0.50    0.05    --  -46.40 -57.00  60.00  174
 18  ω   -129.00 -30.00   0.50    0.05    -- -103.00  85.00 -31.00  198
 19  ω   -174.00 -89.00   0.50    0.05    -- -103.00 -15.00  90.00  170
 20  ω   -174.00 -80.00   0.50    0.05    -- -103.00 -77.00  30.00  188
 21  ω   -174.00 -90.00   0.50    0.05    -- -103.00 -45.00  90.00  168
 22  ω   -174.00 -90.00   0.50    0.05    -- -103.00 -30.00 120.00  168
 23  ω   -174.00 -90.00   0.50    0.05    -- -103.00 -45.00 150.00  168
 24  ω   -174.00 -86.00   0.50    0.05    -- -103.00 -61.00 -60.00  176
 25  ω   -174.00 -90.00   0.50    0.05    -- -103.00 -45.00 -90.00  168
 26  ω   -174.00 -90.00   0.50    0.05    -- -103.00 -30.00-150.00  168
 27  ω   -174.00 -79.00   0.50    0.05    -- -103.00 -85.00-150.00  190
 28  ω   -118.00 -73.00   0.50    0.05    --  -46.40-125.00   0.00   90
 29  ω     32.00  74.00   0.50    0.05    --  104.54 -61.00 -30.00   84
 30  ω     32.00  74.00   0.50    0.05    --  104.54 -61.00   0.00   84
 31  ω     85.00 176.00   0.50    0.05    --  104.54  85.00 -31.00  182
 32  ω     24.00 119.00   0.50    0.05    --   46.40  77.00  90.00  190
 33  ω    -28.00  29.00   0.50    0.05    --   46.40 -19.00 -90.00  114
 34  ω    -25.00  73.00   0.50    0.05    --   46.40 -85.00-150.00  196
 35  ω     32.00 131.00   0.50    0.05    --  104.54 -85.00-150.00  198
 36  ω     32.00 105.00   0.50    0.05    --  104.54 -95.00-180.00  146
 37  ω     32.00 111.00   0.50    0.05    --  104.54-125.00   0.00  158
 38  ω     32.00 105.00   0.50    0.05    --  104.54 -95.00 150.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1046257000
_diffrn_orient_matrix_UB_12      0.0006002000
_diffrn_orient_matrix_UB_13      0.1899916000
_diffrn_orient_matrix_UB_21      0.0949539000
_diffrn_orient_matrix_UB_22      0.0628792000
_diffrn_orient_matrix_UB_23      -0.0085896000
_diffrn_orient_matrix_UB_31      -0.1813210000
_diffrn_orient_matrix_UB_32      0.0332424000
_diffrn_orient_matrix_UB_33      0.0129550000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.847
_reflns_Friedel_fraction_max     0.783
_reflns_number_gt                2275
_reflns_number_total             2341
_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 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    2018.3
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 979 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.20(18)
_refine_ls_extinction_coef       0.0030(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2341
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.084
_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)+(0.0839P)²+0.0899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1139
_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, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1S(H1SD,H1SE), C2S(H2SA,H2SB), C3S(H3SA,H3SB)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), N1S(H1SA,H1SB,H1SC)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.9460(4) 0.53513(12) 0.9374(3) 0.0560(6) Uani 1 1 d . . . . .
O2 O 0.6772(4) 0.36145(10) 0.6389(3) 0.0589(7) Uani 1 1 d . . . . .
N1 N 0.7079(4) 0.54945(9) 0.6808(3) 0.0347(5) Uani 1 1 d . . . . .
N2 N 0.8044(4) 0.44919(11) 0.7889(3) 0.0388(5) Uani 1 1 d . . . . .
N3 N 0.4440(3) 0.55163(11) 0.4051(3) 0.0361(5) Uani 1 1 d . . . . .
N4 N 0.4129(4) 0.44922(11) 0.3684(3) 0.0387(5) Uani 1 1 d . . . . .
H4 H 0.371783 0.414118 0.321866 0.046 Uiso 1 1 calc R U . . .
C1 C 0.8265(5) 0.51310(14) 0.8100(4) 0.0383(6) Uani 1 1 d . . . . .
C2 C 0.6778(5) 0.41784(13) 0.6469(4) 0.0391(6) Uani 1 1 d . . . . .
C3 C 0.5580(4) 0.45926(12) 0.5229(4) 0.0332(6) Uani 1 1 d . . . . .
C4 C 0.5736(4) 0.52209(11) 0.5405(3) 0.0313(5) Uani 1 1 d . . . . .
C5 C 0.3486(5) 0.50526(13) 0.3050(4) 0.0390(6) Uani 1 1 d . . . . .
H5 H 0.247627 0.511283 0.201631 0.047 Uiso 1 1 calc R U . . .
C6 C 0.9240(6) 0.41222(17) 0.9324(5) 0.0546(9) Uani 1 1 d . . . . .
H6A H 1.063060 0.420306 0.959194 0.082 Uiso 1 1 calc R U . . .
H6B H 0.897467 0.369191 0.907210 0.082 Uiso 1 1 calc R U . . .
H6C H 0.890167 0.422874 1.025067 0.082 Uiso 1 1 calc R U . . .
C7 C 0.7308(5) 0.61628(13) 0.6875(4) 0.0459(7) Uani 1 1 d . . . . .
H7A H 0.751435 0.630303 0.591023 0.069 Uiso 1 1 calc R U . . .
H7B H 0.843534 0.627535 0.784890 0.069 Uiso 1 1 calc R U . . .
H7C H 0.612535 0.635091 0.690849 0.069 Uiso 1 1 calc R U . . .
O1S O 0.2414(3) 0.33999(9) 0.2585(3) 0.0455(5) Uani 1 1 d . . . . .
O2S O 0.0523(3) 0.26179(9) 0.1296(3) 0.0420(5) Uani 1 1 d . . . . .
N1S N 0.8789(3) 0.30810(10) 0.3474(3) 0.0358(5) Uani 1 1 d . . . . .
H1SA H 0.928980 0.298680 0.271923 0.043 Uiso 1 1 calc R U . . .
H1SB H 0.951904 0.290280 0.443200 0.043 Uiso 1 1 calc R U . . .
H1SC H 0.880828 0.348868 0.360687 0.043 Uiso 1 1 calc R U . . .
C1S C 0.3344(4) 0.28240(13) 0.0634(3) 0.0391(6) Uani 1 1 d . . . . .
H1SD H 0.263795 0.294989 -0.050622 0.047 Uiso 1 1 calc R U . . .
H1SE H 0.353732 0.238080 0.063568 0.047 Uiso 1 1 calc R U . . .
C2S C 0.5386(4) 0.31321(12) 0.1277(3) 0.0362(6) Uani 1 1 d . . . . .
H2SA H 0.600478 0.307856 0.047836 0.043 Uiso 1 1 calc R U . . .
H2SB H 0.523253 0.357133 0.141097 0.043 Uiso 1 1 calc R U . . .
C3S C 0.6711(4) 0.28563(13) 0.2917(3) 0.0368(6) Uani 1 1 d . . . . .
H3SA H 0.617501 0.295854 0.374578 0.044 Uiso 1 1 calc R U . . .
H3SB H 0.670411 0.241026 0.281442 0.044 Uiso 1 1 calc R U . . .
C8 C 0.2023(4) 0.29608(11) 0.1589(3) 0.0311(5) 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 1.217(4) . ?
O2 C2 1.223(4) . ?
N1 C1 1.376(4) . ?
N1 C4 1.376(3) . ?
N1 C7 1.456(3) . ?
N2 C1 1.398(4) . ?
N2 C2 1.405(4) . ?
N2 C6 1.462(4) . ?
N3 C4 1.358(4) . ?
N3 C5 1.338(4) . ?
N4 H4 0.8600 . ?
N4 C3 1.376(4) . ?
N4 C5 1.342(4) . ?
C2 C3 1.420(4) . ?
C3 C4 1.369(3) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
O1S C8 1.247(3) . ?
O2S C8 1.260(3) . ?
N1S H1SA 0.8900 . ?
N1S H1SB 0.8900 . ?
N1S H1SC 0.8900 . ?
N1S C3S 1.478(4) . ?
C1S H1SD 0.9700 . ?
C1S H1SE 0.9700 . ?
C1S C2S 1.523(4) . ?
C1S C8 1.520(4) . ?
C2S H2SA 0.9700 . ?
C2S H2SB 0.9700 . ?
C2S C3S 1.511(3) . ?
C3S H3SA 0.9700 . ?
C3S H3SB 0.9700 . ?

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 C7 120.7(2) . . ?
C4 N1 C1 119.6(2) . . ?
C4 N1 C7 119.7(2) . . ?
C1 N2 C2 126.8(3) . . ?
C1 N2 C6 115.4(3) . . ?
C2 N2 C6 117.8(2) . . ?
C5 N3 C4 103.3(2) . . ?
C3 N4 H4 126.9 . . ?
C5 N4 H4 126.9 . . ?
C5 N4 C3 106.1(2) . . ?
O1 C1 N1 122.0(3) . . ?
O1 C1 N2 121.0(3) . . ?
N1 C1 N2 117.0(2) . . ?
O2 C2 N2 121.4(3) . . ?
O2 C2 C3 126.8(3) . . ?
N2 C2 C3 111.8(2) . . ?
N4 C3 C2 131.7(2) . . ?
C4 C3 N4 105.5(2) . . ?
C4 C3 C2 122.8(3) . . ?
N3 C4 N1 126.4(2) . . ?
N3 C4 C3 111.7(2) . . ?
C3 C4 N1 121.9(2) . . ?
N3 C5 N4 113.4(3) . . ?
N3 C5 H5 123.3 . . ?
N4 C5 H5 123.3 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H1SA N1S H1SB 109.5 . . ?
H1SA N1S H1SC 109.5 . . ?
H1SB N1S H1SC 109.5 . . ?
C3S N1S H1SA 109.5 . . ?
C3S N1S H1SB 109.5 . . ?
C3S N1S H1SC 109.5 . . ?
H1SD C1S H1SE 107.4 . . ?
C2S C1S H1SD 108.3 . . ?
C2S C1S H1SE 108.3 . . ?
C8 C1S H1SD 108.3 . . ?
C8 C1S H1SE 108.3 . . ?
C8 C1S C2S 116.1(2) . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
H2SA C2S H2SB 108.1 . . ?
C3S C2S C1S 110.7(2) . . ?
C3S C2S H2SA 109.5 . . ?
C3S C2S H2SB 109.5 . . ?
N1S C3S C2S 112.5(2) . . ?
N1S C3S H3SA 109.1 . . ?
N1S C3S H3SB 109.1 . . ?
C2S C3S H3SA 109.1 . . ?
C2S C3S H3SB 109.1 . . ?
H3SA C3S H3SB 107.8 . . ?
O1S C8 O2S 122.7(3) . . ?
O1S C8 C1S 120.6(2) . . ?
O2S C8 C1S 116.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C2 C3 N4 1.2(6) . . . . ?
O2 C2 C3 C4 -177.7(3) . . . . ?
N2 C2 C3 N4 -178.5(3) . . . . ?
N2 C2 C3 C4 2.6(4) . . . . ?
N4 C3 C4 N1 -179.1(3) . . . . ?
N4 C3 C4 N3 0.5(3) . . . . ?
C1 N1 C4 N3 178.5(3) . . . . ?
C1 N1 C4 C3 -2.0(5) . . . . ?
C1 N2 C2 O2 176.4(3) . . . . ?
C1 N2 C2 C3 -3.8(4) . . . . ?
C2 N2 C1 O1 -177.7(3) . . . . ?
C2 N2 C1 N1 2.2(5) . . . . ?
C2 C3 C4 N1 0.1(5) . . . . ?
C2 C3 C4 N3 179.7(3) . . . . ?
C3 N4 C5 N3 1.4(3) . . . . ?
C4 N1 C1 O1 -179.2(3) . . . . ?
C4 N1 C1 N2 0.9(4) . . . . ?
C4 N3 C5 N4 -1.1(3) . . . . ?
C5 N3 C4 N1 179.9(3) . . . . ?
C5 N3 C4 C3 0.3(3) . . . . ?
C5 N4 C3 C2 179.8(3) . . . . ?
C5 N4 C3 C4 -1.1(3) . . . . ?
C6 N2 C1 O1 3.7(5) . . . . ?
C6 N2 C1 N1 -176.4(3) . . . . ?
C6 N2 C2 O2 -5.0(5) . . . . ?
C6 N2 C2 C3 174.8(3) . . . . ?
C7 N1 C1 O1 4.2(5) . . . . ?
C7 N1 C1 N2 -175.7(3) . . . . ?
C7 N1 C4 N3 -4.9(5) . . . . ?
C7 N1 C4 C3 174.6(3) . . . . ?
C1S C2S C3S N1S 172.2(2) . . . . ?
C2S C1S C8 O1S 15.3(4) . . . . ?
C2S C1S C8 O2S -165.9(2) . . . . ?
C8 C1S C2S C3S 69.6(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 5.298
_oxdiff_exptl_absorpt_empirical_full_min 0.141
####################################################################### 
# 
# 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_samp7047b
_database_code_depnum_ccdc_archive 'CCDC 2307423'
loop_
_audit_author_name
_audit_author_address
'Qi Li'
;Institue of Materia Medica Chinese Academy of Medical Science
China
;
_audit_update_record             
;
2024-12-01 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_audit_creation_date             2024-06-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H8 N4 O2, C6 H14 N4 O2, 2(H2 O)'
_chemical_formula_sum            'C13 H26 N8 O6'
_chemical_formula_weight         390.42
_chemical_absolute_configuration rm
_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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.8709(2)
_cell_length_b                   7.7140(3)
_cell_length_c                   11.1553(3)
_cell_angle_alpha                72.564(3)
_cell_angle_beta                 81.718(3)
_cell_angle_gamma                72.804(3)
_cell_volume                     459.59(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5170
_cell_measurement_temperature    301.9(5)
_cell_measurement_theta_max      75.1290
_cell_measurement_theta_min      3.9360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.956
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.59a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       blocked
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8049
_diffrn_reflns_point_group_measured_fraction_full 0.856
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.318
_diffrn_reflns_theta_min         4.162
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.9(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00  26.00   0.50    0.59    --  -46.53  91.00 115.00  204
  2  ω    -25.00  76.00   0.50    0.59    --   46.53 -91.00   1.00  202
  3  ω   -174.00 -79.00   0.50    2.35    -- -103.00 -91.00   1.00  190
  4  ω   -105.00 -30.00   0.50    2.35    -- -103.00  91.00 115.00  150
  5  ω     85.00 176.00   0.50    2.35    --  104.54  91.00 115.00  182
  6  ω    -23.00  29.00   0.50    0.59    --  -46.53  19.00   0.00  104
  7  ω   -118.00 -73.00   0.50    0.59    --  -46.53-125.00  90.00   90
  8  ω    -26.00  46.00   0.50    0.59    --   46.53 -38.00  90.00  144
  9  ω    -28.00  29.00   0.50    0.59    --   46.53 -19.00   0.00  114
 10  ω    -68.00 -30.00   0.50    2.35    -- -103.00  61.00 120.00   76
 11  ω    -68.00 -30.00   0.50    2.35    -- -103.00  61.00  90.00   76
 12  ω   -174.00 -83.00   0.50    2.35    -- -103.00 -95.00 120.00  182
 13  ω   -174.00 -86.00   0.50    2.35    -- -103.00 -61.00  30.00  176
 14  ω    -68.00 -30.00   0.50    2.35    -- -103.00  61.00 -30.00   76
 15  ω    -68.00 -30.00   0.50    2.35    -- -103.00  61.00-180.00   76
 16  ω    -68.00 -30.00   0.50    2.35    -- -103.00  61.00-120.00   76
 17  ω     32.00 105.00   0.50    2.35    --  104.54 -95.00 -90.00  146
 18  ω     32.00  74.00   0.50    2.35    --  104.54 -61.00   0.00   84
 19  ω     32.00 111.00   0.50    2.35    --  104.54-125.00-180.00  158
 20  ω     32.00 108.00   0.50    2.35    --  104.54 -77.00-180.00  152
 21  ω     32.00 111.00   0.50    2.35    --  104.54-125.00-120.00  158
 22  ω     91.00 178.00   0.50    2.35    --  104.54  15.00 -90.00  174
 23  ω     92.00 178.00   0.50    2.35    --  104.54  30.00-180.00  172
 24  ω     32.00  74.00   0.50    2.35    --  104.54 -61.00 -90.00   84
 25  ω     32.00 105.00   0.50    2.35    --  104.54 -95.00 -30.00  146
 26  ω     88.00 176.00   0.50    2.35    --  104.54  61.00  30.00  176
 27  ω     32.00 111.00   0.50    2.35    --  104.54-125.00   0.00  158
 28  ω     32.00 106.00   0.50    2.35    --  104.54 -91.00   1.00  148
 29  ω   -118.00 -24.00   0.50    0.59    --  -46.53 -77.00 -30.00  188
 30  ω   -118.00 -32.00   0.50    0.59    --  -46.53 -57.00  60.00  172
 31  ω     32.00 118.00   0.50    0.59    --   46.53  57.00  30.00  172
 32  ω     24.00 118.00   0.50    0.59    --   46.53  77.00-120.00  188
 33  ω     24.00 118.00   0.50    0.59    --   46.53  77.00-180.00  188
 34  ω     24.00 118.00   0.50    0.59    --   46.53  77.00 -60.00  188
 35  ω     24.00 118.00   0.50    0.59    --   46.53  77.00  90.00  188
 36  ω   -174.00 -86.00   0.50    2.35    -- -103.00 -61.00 150.00  176
 37  ω     92.00 178.00   0.50    2.35    --  104.54  30.00-150.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1485389000
_diffrn_orient_matrix_UB_12      0.1463099000
_diffrn_orient_matrix_UB_13      0.0690588000
_diffrn_orient_matrix_UB_21      0.1554859000
_diffrn_orient_matrix_UB_22      -0.1009683000
_diffrn_orient_matrix_UB_23      0.1138357000
_diffrn_orient_matrix_UB_31      0.1717345000
_diffrn_orient_matrix_UB_32      0.1248699000
_diffrn_orient_matrix_UB_33      -0.0574752000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    0.714
_reflns_Friedel_fraction_max     0.643
_reflns_number_gt                2806
_reflns_number_total             3092
_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 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    2018.3
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 1037 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.060
_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)+(0.0858P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1198
_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, All N(H,H) groups, All
  N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1W-H1WA
 0.85 with sigma of 0.02
 O2W-H2WA
 0.85 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1S(H1S)
3.b Secondary CH2 refined with riding coordinates:
 C2S(H2SA,H2SB), C3S(H3SC,H3SD), C4S(H4SC,H4SD)
3.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C5(H5)
3.d X=CH2 refined with riding coordinates:
 N3S(H3SA,H3SB), N4S(H4SA,H4SB)
3.e Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), N1S(H1SA,H1SB,H1SC)
;
_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
O1 O 0.9701(5) 0.5477(5) 0.2886(3) 0.0596(8) Uani 1 1 d . . . . .
O2 O 0.2532(5) 0.9405(4) 0.1469(2) 0.0497(7) Uani 1 1 d . . . . .
N1 N 0.6928(5) 0.6464(4) 0.4350(2) 0.0374(7) Uani 1 1 d . . . . .
N2 N 0.6056(5) 0.7373(4) 0.2220(2) 0.0403(7) Uani 1 1 d . . . . .
N3 N 0.3686(5) 0.7696(4) 0.5726(2) 0.0365(6) Uani 1 1 d . . . . .
N4 N 0.1014(5) 0.9433(4) 0.4219(2) 0.0386(6) Uani 1 1 d . . . . .
H4 H -0.026326 1.017573 0.386889 0.046 Uiso 1 1 calc R U . . .
C1 C 0.7693(6) 0.6380(5) 0.3151(3) 0.0411(8) Uani 1 1 d . . . . .
C2 C 0.3771(6) 0.8520(5) 0.2393(3) 0.0368(7) Uani 1 1 d . . . . .
C3 C 0.3095(5) 0.8522(5) 0.3664(3) 0.0335(7) Uani 1 1 d . . . . .
C4 C 0.4658(6) 0.7507(4) 0.4597(3) 0.0328(7) Uani 1 1 d . . . . .
C5 C 0.1470(6) 0.8884(5) 0.5419(3) 0.0387(7) Uani 1 1 d . . . . .
H5 H 0.034612 0.928055 0.602646 0.046 Uiso 1 1 calc R U . . .
C6 C 0.8604(7) 0.5488(6) 0.5342(4) 0.0523(10) Uani 1 1 d . . . . .
H6A H 0.916957 0.639214 0.556367 0.078 Uiso 1 1 calc R U . . .
H6B H 0.993104 0.461153 0.504614 0.078 Uiso 1 1 calc R U . . .
H6C H 0.781148 0.481954 0.606848 0.078 Uiso 1 1 calc R U . . .
C7 C 0.6923(8) 0.7233(7) 0.0945(3) 0.0601(12) Uani 1 1 d . . . . .
H7A H 0.559191 0.744082 0.046298 0.090 Uiso 1 1 calc R U . . .
H7B H 0.797250 0.600018 0.098685 0.090 Uiso 1 1 calc R U . . .
H7C H 0.777411 0.816684 0.055054 0.090 Uiso 1 1 calc R U . . .
O1S O 0.5912(4) 0.2559(4) 0.9069(2) 0.0436(6) Uani 1 1 d . . . . .
O2S O 0.8415(4) 0.0623(5) 0.8046(2) 0.0546(8) Uani 1 1 d . . . . .
N1S N 0.2132(4) 0.1452(4) 0.8861(2) 0.0333(6) Uani 1 1 d . . . . .
H1SA H 0.091155 0.119920 0.862116 0.040 Uiso 1 1 calc R U . . .
H1SB H 0.175601 0.266797 0.883342 0.040 Uiso 1 1 calc R U . . .
H1SC H 0.244987 0.075441 0.964322 0.040 Uiso 1 1 calc R U . . .
N2S N 0.6424(4) 0.2009(4) 0.3403(2) 0.0365(6) Uani 1 1 d . . . . .
N3S N 0.3927(5) 0.3431(5) 0.1754(2) 0.0474(8) Uani 1 1 d . . . . .
H3SA H 0.279535 0.388174 0.224842 0.057 Uiso 1 1 calc R U . . .
H3SB H 0.370104 0.365845 0.097064 0.057 Uiso 1 1 calc R U . . .
N4S N 0.7767(5) 0.1710(6) 0.1426(3) 0.0530(9) Uani 1 1 d . . . . .
H4SA H 0.913525 0.104022 0.170520 0.064 Uiso 1 1 calc R U . . .
H4SB H 0.752595 0.194435 0.064379 0.064 Uiso 1 1 calc R U . . .
C1S C 0.4283(5) 0.1004(4) 0.7995(2) 0.0280(6) Uani 1 1 d . . . . .
H1S H 0.469984 -0.033931 0.803740 0.034 Uiso 1 1 calc R U . . .
C2S C 0.3630(5) 0.2165(5) 0.6657(2) 0.0308(6) Uani 1 1 d . . . . .
H2SA H 0.213270 0.200524 0.649928 0.037 Uiso 1 1 calc R U . . .
H2SB H 0.338296 0.348805 0.659640 0.037 Uiso 1 1 calc R U . . .
C3S C 0.5509(5) 0.1636(5) 0.5641(2) 0.0311(6) Uani 1 1 d . . . . .
H3SC H 0.692041 0.201037 0.569634 0.037 Uiso 1 1 calc R U . . .
H3SD H 0.596256 0.027879 0.578029 0.037 Uiso 1 1 calc R U . . .
C4S C 0.4580(5) 0.2584(5) 0.4339(2) 0.0331(7) Uani 1 1 d . . . . .
H4SC H 0.315868 0.222508 0.427939 0.040 Uiso 1 1 calc R U . . .
H4SD H 0.415979 0.394290 0.418513 0.040 Uiso 1 1 calc R U . . .
C5S C 0.6029(6) 0.2381(5) 0.2201(3) 0.0343(7) Uani 1 1 d . . . . .
C8 C 0.6378(5) 0.1438(5) 0.8404(2) 0.0325(7) Uani 1 1 d . . . . .
O1W O 0.5171(7) 0.6443(4) 0.8193(3) 0.0667(9) Uani 1 1 d D . . . .
H1WA H 0.528(14) 0.525(4) 0.845(7) 0.100 Uiso 1 1 d D U . . .
H1WB H 0.458(16) 0.701(13) 0.744(9) 0.13(3) Uiso 1 1 d . . . . .
O2W O 0.0246(9) 0.5407(7) 0.8635(5) 0.0866(13) Uani 1 1 d D . . . .
H2WA H 0.108(15) 0.613(11) 0.869(9) 0.130 Uiso 1 1 d D U . . .
H2WB H -0.108(14) 0.615(10) 0.844(6) 0.079(19) 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 1.225(4) . ?
O2 C2 1.248(4) . ?
N1 C1 1.362(4) . ?
N1 C4 1.376(4) . ?
N1 C6 1.461(4) . ?
N2 C1 1.402(4) . ?
N2 C2 1.395(4) . ?
N2 C7 1.464(4) . ?
N3 C4 1.337(4) . ?
N3 C5 1.373(4) . ?
N4 H4 0.8600 . ?
N4 C3 1.380(4) . ?
N4 C5 1.318(4) . ?
C2 C3 1.417(4) . ?
C3 C4 1.378(4) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
O1S C8 1.249(4) . ?
O2S C8 1.246(4) . ?
N1S H1SA 0.8900 . ?
N1S H1SB 0.8900 . ?
N1S H1SC 0.8900 . ?
N1S C1S 1.496(3) . ?
N2S C4S 1.458(4) . ?
N2S C5S 1.324(4) . ?
N3S H3SA 0.8600 . ?
N3S H3SB 0.8600 . ?
N3S C5S 1.331(4) . ?
N4S H4SA 0.8600 . ?
N4S H4SB 0.8600 . ?
N4S C5S 1.326(4) . ?
C1S H1S 0.9800 . ?
C1S C2S 1.529(3) . ?
C1S C8 1.527(4) . ?
C2S H2SA 0.9700 . ?
C2S H2SB 0.9700 . ?
C2S C3S 1.522(3) . ?
C3S H3SC 0.9700 . ?
C3S H3SD 0.9700 . ?
C3S C4S 1.516(3) . ?
C4S H4SC 0.9700 . ?
C4S H4SD 0.9700 . ?
O1W H1WA 0.86(3) . ?
O1W H1WB 0.89(9) . ?
O2W H2WA 0.86(3) . ?
O2W H2WB 0.83(8) . ?

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 C4 120.1(3) . . ?
C1 N1 C6 118.4(3) . . ?
C4 N1 C6 121.5(3) . . ?
C1 N2 C7 115.4(3) . . ?
C2 N2 C1 126.2(3) . . ?
C2 N2 C7 118.4(3) . . ?
C4 N3 C5 101.2(2) . . ?
C3 N4 H4 128.6 . . ?
C5 N4 H4 128.6 . . ?
C5 N4 C3 102.8(3) . . ?
O1 C1 N1 122.4(3) . . ?
O1 C1 N2 120.9(3) . . ?
N1 C1 N2 116.8(3) . . ?
O2 C2 N2 119.8(3) . . ?
O2 C2 C3 126.5(3) . . ?
N2 C2 C3 113.7(3) . . ?
N4 C3 C2 131.5(3) . . ?
C4 C3 N4 107.8(2) . . ?
C4 C3 C2 120.7(3) . . ?
N1 C4 C3 122.4(2) . . ?
N3 C4 N1 126.1(3) . . ?
N3 C4 C3 111.5(3) . . ?
N3 C5 H5 121.7 . . ?
N4 C5 N3 116.7(3) . . ?
N4 C5 H5 121.7 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H1SA N1S H1SB 109.5 . . ?
H1SA N1S H1SC 109.5 . . ?
H1SB N1S H1SC 109.5 . . ?
C1S N1S H1SA 109.5 . . ?
C1S N1S H1SB 109.5 . . ?
C1S N1S H1SC 109.5 . . ?
C5S N2S C4S 123.2(3) . . ?
H3SA N3S H3SB 120.0 . . ?
C5S N3S H3SA 120.0 . . ?
C5S N3S H3SB 120.0 . . ?
H4SA N4S H4SB 120.0 . . ?
C5S N4S H4SA 120.0 . . ?
C5S N4S H4SB 120.0 . . ?
N1S C1S H1S 109.1 . . ?
N1S C1S C2S 107.8(2) . . ?
N1S C1S C8 109.5(2) . . ?
C2S C1S H1S 109.1 . . ?
C8 C1S H1S 109.1 . . ?
C8 C1S C2S 112.2(2) . . ?
C1S C2S H2SA 108.8 . . ?
C1S C2S H2SB 108.8 . . ?
H2SA C2S H2SB 107.7 . . ?
C3S C2S C1S 114.0(2) . . ?
C3S C2S H2SA 108.8 . . ?
C3S C2S H2SB 108.8 . . ?
C2S C3S H3SC 109.4 . . ?
C2S C3S H3SD 109.4 . . ?
H3SC C3S H3SD 108.0 . . ?
C4S C3S C2S 111.3(2) . . ?
C4S C3S H3SC 109.4 . . ?
C4S C3S H3SD 109.4 . . ?
N2S C4S C3S 109.2(2) . . ?
N2S C4S H4SC 109.8 . . ?
N2S C4S H4SD 109.8 . . ?
C3S C4S H4SC 109.8 . . ?
C3S C4S H4SD 109.8 . . ?
H4SC C4S H4SD 108.3 . . ?
N2S C5S N3S 121.2(3) . . ?
N2S C5S N4S 119.4(3) . . ?
N4S C5S N3S 119.4(3) . . ?
O1S C8 C1S 117.7(3) . . ?
O2S C8 O1S 125.8(3) . . ?
O2S C8 C1S 116.5(3) . . ?
H1WA O1W H1WB 114(8) . . ?
H2WA O2W H2WB 103(8) . . ?

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 N4 0.2(7) . . . . ?
O2 C2 C3 C4 -178.6(3) . . . . ?
N2 C2 C3 N4 -179.1(4) . . . . ?
N2 C2 C3 C4 2.1(5) . . . . ?
N4 C3 C4 N1 -178.6(3) . . . . ?
N4 C3 C4 N3 0.8(4) . . . . ?
C1 N1 C4 N3 179.5(3) . . . . ?
C1 N1 C4 C3 -1.1(5) . . . . ?
C1 N2 C2 O2 176.3(3) . . . . ?
C1 N2 C2 C3 -4.3(5) . . . . ?
C2 N2 C1 O1 -176.7(4) . . . . ?
C2 N2 C1 N1 3.8(5) . . . . ?
C2 C3 C4 N1 0.4(5) . . . . ?
C2 C3 C4 N3 179.9(3) . . . . ?
C3 N4 C5 N3 0.7(4) . . . . ?
C4 N1 C1 O1 179.6(4) . . . . ?
C4 N1 C1 N2 -0.9(5) . . . . ?
C4 N3 C5 N4 -0.2(4) . . . . ?
C5 N3 C4 N1 179.1(3) . . . . ?
C5 N3 C4 C3 -0.4(4) . . . . ?
C5 N4 C3 C2 -179.8(4) . . . . ?
C5 N4 C3 C4 -0.9(4) . . . . ?
C6 N1 C1 O1 2.1(6) . . . . ?
C6 N1 C1 N2 -178.4(3) . . . . ?
C6 N1 C4 N3 -3.0(5) . . . . ?
C6 N1 C4 C3 176.4(4) . . . . ?
C7 N2 C1 O1 0.3(6) . . . . ?
C7 N2 C1 N1 -179.2(4) . . . . ?
C7 N2 C2 O2 -0.5(5) . . . . ?
C7 N2 C2 C3 178.8(4) . . . . ?
N1S C1S C2S C3S -170.9(3) . . . . ?
N1S C1S C8 O1S -21.1(3) . . . . ?
N1S C1S C8 O2S 158.4(3) . . . . ?
C1S C2S C3S C4S 170.0(3) . . . . ?
C2S C1S C8 O1S 98.6(3) . . . . ?
C2S C1S C8 O2S -81.8(3) . . . . ?
C2S C3S C4S N2S -179.0(3) . . . . ?
C4S N2S C5S N3S 4.7(6) . . . . ?
C4S N2S C5S N4S -176.0(4) . . . . ?
C5S N2S C4S C3S 169.8(3) . . . . ?
C8 C1S C2S C3S 68.4(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 3.681
_oxdiff_exptl_absorpt_empirical_full_min 0.198
