# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_cu_20220905_zm_nlg_3_0m
_database_code_depnum_ccdc_archive 'CCDC 2241992'
loop_
_audit_author_name
_audit_author_address
'Yongxing Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-02-15 deposited with the CCDC.	2023-05-31 downloaded from the CCDC.
;
_audit_creation_date             2023-02-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        123
_chemical_formula_moiety         'C3 H4 N10 O2, C3 H7 N O'
_chemical_formula_sum            'C6 H11 N11 O3'
_chemical_formula_weight         285.26
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.7982(3)
_cell_length_b                   25.3702(15)
_cell_length_c                   12.2141(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.171(4)
_cell_angle_gamma                90
_cell_volume                     1176.72(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2977
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      67.936
_cell_measurement_theta_min      3.485
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.143
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5779
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_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    1.610
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8747
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.384
_diffrn_reflns_theta_min         3.484
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1623
_reflns_number_total             2162
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0940
_refine_ls_restrained_S_all      1.090
_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)+(0.1528P)²+1.4653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2577
_refine_ls_wR_factor_ref         0.2714
_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.a Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.5671(11) 0.40164(13) 0.6656(3) 0.0552(10) Uani 1 1 d . . . A 4
O2 O 0.4092(13) 0.36420(15) 0.5119(3) 0.0648(12) Uani 1 1 d . . . A 4
N1 N 0.7206(12) 0.43734(16) 0.5109(3) 0.0481(11) Uani 1 1 d . . . A 4
N2 N 0.9231(10) 0.48585(14) 0.3649(3) 0.0392(9) Uani 1 1 d . . . A 4
N3 N 0.6285(11) 0.40977(14) 0.3233(3) 0.0407(9) Uani 1 1 d . . . A 4
N4 N 1.0475(12) 0.51430(16) 0.1855(3) 0.0461(10) Uani 1 1 d . . . A 4
H4A H 1.003(14) 0.510(2) 0.118(5) 0.043(13) Uiso 1 1 d . . . B 4
N5 N 0.7416(10) 0.43563(13) 0.2294(3) 0.0380(9) Uani 1 1 d . . . A 4
N6 N 0.4797(11) 0.37273(15) 0.1063(3) 0.0395(9) Uani 1 1 d . . . A 4
H6 H 0.406(14) 0.349(2) 0.146(4) 0.040(13) Uiso 1 1 d . . . C 4
N7 N 0.7423(11) 0.44043(14) 0.0344(3) 0.0426(10) Uani 1 1 d . . . A 4
N8 N 0.6065(11) 0.40855(15) -0.0460(3) 0.0444(10) Uani 1 1 d . . . A 4
N9 N 0.4506(11) 0.36811(14) -0.0045(3) 0.0413(10) Uani 1 1 d . . . A 4
N11 N 0.5573(12) 0.39858(14) 0.5649(3) 0.0449(10) Uani 1 1 d . . . A 4
C1 C 0.7472(13) 0.44195(16) 0.3992(3) 0.0391(10) Uani 1 1 d . . . A 4
C2 C 0.9140(12) 0.48136(16) 0.2565(3) 0.0354(10) Uani 1 1 d . . . A 4
C3 C 0.6576(12) 0.41717(17) 0.1253(3) 0.0373(10) Uani 1 1 d . . . A 4
O3 O 1.1853(11) 0.29534(14) 0.2027(3) 0.0580(10) Uani 1 1 d . . . D 4
N10 N 0.9671(11) 0.25153(14) 0.3467(3) 0.0426(10) Uani 1 1 d . . . D 4
C4 C 1.1109(14) 0.29288(18) 0.3014(4) 0.0455(11) Uani 1 1 d . . . D 4
H4 H 1.1612 0.3226 0.3464 0.055 Uiso 1 1 calc R . . D 4
C5 C 0.8929(16) 0.2506(2) 0.4632(4) 0.0529(13) Uani 1 1 d . . . D 4
H5A H 0.6381 0.2482 0.4732 0.079 Uiso 1 1 calc GR . . D 4
H5B H 0.9821 0.2830 0.4976 0.079 Uiso 1 1 calc GR . . D 4
H5C H 1.0088 0.2201 0.4973 0.079 Uiso 1 1 calc GR . . D 4
C6 C 0.8819(17) 0.2051(2) 0.2817(5) 0.0596(14) Uani 1 1 d . . . D 4
H6A H 1.0113 0.1747 0.3112 0.089 Uiso 1 1 calc GR . . D 4
H6B H 0.9487 0.2111 0.2056 0.089 Uiso 1 1 calc GR . . D 4
H6C H 0.6283 0.1983 0.2844 0.089 Uiso 1 1 calc GR . . D 4
H4B H 1.158(18) 0.544(3) 0.214(6) 0.08(2) Uiso 1 1 d . . . E 4
H1 H 0.776(16) 0.466(2) 0.556(5) 0.058(16) 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 N11 1.232(5) . ?
O2 N11 1.217(5) . ?
N1 N11 1.343(5) . ?
N1 C1 1.375(5) . ?
N1 H1 0.92(6) . ?
N2 C1 1.369(6) . ?
N2 C2 1.330(5) . ?
N3 N5 1.397(5) . ?
N3 C1 1.308(6) . ?
N4 H4A 0.85(6) . ?
N4 C2 1.314(6) . ?
N4 H4B 0.93(8) . ?
N5 C2 1.370(5) . ?
N5 C3 1.386(5) . ?
N6 H6 0.82(6) . ?
N6 N9 1.361(5) . ?
N6 C3 1.332(6) . ?
N7 N8 1.365(5) . ?
N7 C3 1.303(6) . ?
N8 N9 1.294(5) . ?
O3 C4 1.246(6) . ?
N10 C4 1.310(6) . ?
N10 C5 1.457(6) . ?
N10 C6 1.453(6) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
N11 N1 C1 126.4(4) . . ?
N11 N1 H1 112(4) . . ?
C1 N1 H1 120(4) . . ?
C2 N2 C1 103.4(3) . . ?
C1 N3 N5 100.5(3) . . ?
H4A N4 H4B 124(6) . . ?
C2 N4 H4A 119(4) . . ?
C2 N4 H4B 116(4) . . ?
C2 N5 N3 110.7(3) . . ?
C2 N5 C3 127.4(4) . . ?
C3 N5 N3 121.7(3) . . ?
N9 N6 H6 120(4) . . ?
C3 N6 H6 134(4) . . ?
C3 N6 N9 106.0(3) . . ?
C3 N7 N8 104.4(4) . . ?
N9 N8 N7 110.9(3) . . ?
N8 N9 N6 107.1(3) . . ?
O1 N11 N1 116.0(4) . . ?
O2 N11 O1 125.5(4) . . ?
O2 N11 N1 118.5(4) . . ?
N2 C1 N1 114.8(4) . . ?
N3 C1 N1 128.2(4) . . ?
N3 C1 N2 117.0(4) . . ?
N2 C2 N5 108.4(3) . . ?
N4 C2 N2 126.9(4) . . ?
N4 C2 N5 124.7(4) . . ?
N6 C3 N5 123.5(4) . . ?
N7 C3 N5 124.9(4) . . ?
N7 C3 N6 111.6(4) . . ?
C4 N10 C5 121.0(4) . . ?
C4 N10 C6 120.6(4) . . ?
C6 N10 C5 118.4(4) . . ?
O3 C4 N10 123.6(4) . . ?
O3 C4 H4 118.2 . . ?
N10 C4 H4 118.2 . . ?
N10 C5 H5A 109.5 . . ?
N10 C5 H5B 109.5 . . ?
N10 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N10 C6 H6A 109.5 . . ?
N10 C6 H6B 109.5 . . ?
N10 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
N4 H4A N7 0.85(6) 2.25(6) 2.859(6) 129(5) .
N6 H6 O3 0.82(6) 1.76(6) 2.558(5) 167(5) 1_455
N1 H1 N2 0.92(6) 1.93(6) 2.801(6) 157(5) 3_766

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
N3 N5 C2 N2 1.1(5) . . . . ?
N3 N5 C2 N4 -179.4(4) . . . . ?
N3 N5 C3 N6 -3.2(7) . . . . ?
N3 N5 C3 N7 177.1(4) . . . . ?
N5 N3 C1 N1 -179.2(5) . . . . ?
N5 N3 C1 N2 0.3(5) . . . . ?
N7 N8 N9 N6 0.3(5) . . . . ?
N8 N7 C3 N5 -180.0(4) . . . . ?
N8 N7 C3 N6 0.4(5) . . . . ?
N9 N6 C3 N5 -179.9(4) . . . . ?
N9 N6 C3 N7 -0.2(5) . . . . ?
N11 N1 C1 N2 178.9(5) . . . . ?
N11 N1 C1 N3 -1.6(9) . . . . ?
C1 N1 N11 O1 179.3(5) . . . . ?
C1 N1 N11 O2 -1.7(8) . . . . ?
C1 N2 C2 N4 179.6(5) . . . . ?
C1 N2 C2 N5 -0.8(5) . . . . ?
C1 N3 N5 C2 -0.8(5) . . . . ?
C1 N3 N5 C3 -176.4(4) . . . . ?
C2 N2 C1 N1 179.9(4) . . . . ?
C2 N2 C1 N3 0.4(6) . . . . ?
C2 N5 C3 N6 -178.0(4) . . . . ?
C2 N5 C3 N7 2.4(8) . . . . ?
C3 N5 C2 N2 176.3(4) . . . . ?
C3 N5 C2 N4 -4.1(8) . . . . ?
C3 N6 N9 N8 0.0(5) . . . . ?
C3 N7 N8 N9 -0.4(5) . . . . ?
C5 N10 C4 O3 178.7(5) . . . . ?
C6 N10 C4 O3 -0.5(8) . . . . ?

_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_cu_20221114_zm_nlg_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2241993'
loop_
_audit_author_name
_audit_author_address
'Yongxing Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-02-15 deposited with the CCDC.	2023-05-31 downloaded from the CCDC.
;
_audit_creation_date             2023-02-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        123
_chemical_formula_moiety         'C3 H2 N10 O2, 2(H4 N O), H2 O'
_chemical_formula_sum            'C3 H12 N12 O5'
_chemical_formula_weight         296.25
_chemical_absolute_configuration ?
_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        'C 1 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'

_cell_length_a                   3.66370(10)
_cell_length_b                   24.8780(5)
_cell_length_c                   12.5043(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.1820(10)
_cell_angle_gamma                90
_cell_volume                     1137.95(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5122
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.094
_cell_measurement_theta_min      3.553
_shelx_estimated_absorpt_T_max   0.865
_shelx_estimated_absorpt_T_min   0.843
_exptl_absorpt_coefficient_mu    1.362
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_correction_T_min  0.5077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_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    1.729
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6934
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.097
_diffrn_reflns_theta_min         3.553
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    0.923
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                1972
_reflns_number_total             2007
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 916 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2007
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0243
_refine_ls_restrained_S_all      1.092
_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)+(0.0328P)²+0.2948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0597
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 N12-H12C \\sim N12-H12B
 with sigma of 0.02
3.a Free rotating group:
 O5(H5A,H5B)
3.b Rotating group:
 N12(H12A,H12B), N11(H11A,H11B)
3.c X=CH2 refined with riding coordinates:
 N8(H8A,H8B)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
C1 C 0.4471(6) 0.64327(9) 0.50173(18) 0.0156(5) Uani 1 1 d . . . . .
N1 N 0.4973(5) 0.72750(8) 0.50554(16) 0.0205(5) Uani 1 1 d . . . . .
O1 O 0.9728(4) 0.59794(6) 0.74719(14) 0.0206(4) Uani 1 1 d . . . . .
H1 H 0.9024 0.6189 0.6976 0.031 Uiso 1 1 calc GR . . . .
C2 C 0.1854(6) 0.57528(9) 0.37336(18) 0.0165(5) Uani 1 1 d . . . . .
N2 N 0.6592(6) 0.70862(8) 0.59273(16) 0.0205(5) Uani 1 1 d . . . . .
O2 O 0.7437(5) 0.46315(7) 0.63007(15) 0.0312(5) Uani 1 1 d . . . . .
C3 C 0.3797(6) 0.50686(9) 0.46137(18) 0.0151(4) Uani 1 1 d . . . . .
N3 N 0.6317(5) 0.65443(7) 0.59284(16) 0.0184(4) Uani 1 1 d . . . . .
O3 O 0.6836(5) 0.38385(6) 0.55910(15) 0.0255(4) Uani 1 1 d . . . . .
N4 N 0.3566(6) 0.68683(7) 0.44391(16) 0.0201(5) Uani 1 1 d . . . . .
N5 N 0.3562(5) 0.59145(8) 0.46742(16) 0.0170(4) Uani 1 1 d . . . . .
N6 N 0.4883(5) 0.54661(7) 0.52575(17) 0.0170(4) Uani 1 1 d . . . . .
N7 N 0.1938(5) 0.52191(8) 0.36742(16) 0.0175(4) Uani 1 1 d . . . . .
N8 N 0.0293(6) 0.60864(8) 0.30108(16) 0.0228(5) Uani 1 1 d . . . . .
H8A H -0.0822 0.5957 0.2424 0.027 Uiso 1 1 calc R . . . .
H8B H 0.0378 0.6436 0.3120 0.027 Uiso 1 1 calc R . . . .
N9 N 0.6226(5) 0.43424(8) 0.55511(17) 0.0190(4) Uani 1 1 d . . . . .
N10 N 0.4370(5) 0.45179(7) 0.47045(16) 0.0182(4) Uani 1 1 d . . . . .
N12 N 0.7327(5) 0.55343(7) 0.74908(17) 0.0178(4) Uani 1 1 d D . . . .
H12A H 0.8470 0.5259 0.7805 0.021 Uiso 1 1 d GR . . . .
H12B H 0.5395 0.5617 0.7850 0.021 Uiso 1 1 d DGR . . . .
H12C H 0.664(9) 0.5428(12) 0.679(2) 0.038(9) Uiso 1 1 d D . . . .
O4 O 0.4488(5) 0.31360(7) 0.35094(16) 0.0287(4) Uani 1 1 d . . . . .
H4 H 0.3574 0.2888 0.3124 0.043 Uiso 1 1 calc GR . . . .
N11 N 0.1960(5) 0.32985(8) 0.42516(17) 0.0207(4) Uani 1 1 d . . . . .
H11A H 0.0934 0.3015 0.4543 0.025 Uiso 1 1 d GR . . . .
H11B H 0.3071 0.3492 0.4769 0.025 Uiso 1 1 d GR . . . .
H11C H 0.013(9) 0.3510(12) 0.389(3) 0.027(7) Uiso 1 1 d . . . . .
O5 O 0.1127(5) 0.23507(8) 0.25050(15) 0.0298(4) Uani 1 1 d . . . . .
H5A H -0.0352 0.2478 0.1998 0.045 Uiso 1 1 d G . . . .
H5B H -0.0297 0.2193 0.2942 0.045 Uiso 1 1 d G . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N3 1.322(3) . ?
C1 N4 1.334(3) . ?
C1 N5 1.393(3) . ?
N1 N2 1.300(3) . ?
N1 N4 1.356(3) . ?
O1 H1 0.8400 . ?
O1 N12 1.415(2) . ?
C2 N5 1.362(3) . ?
C2 N7 1.330(3) . ?
C2 N8 1.332(3) . ?
N2 N3 1.352(3) . ?
O2 N9 1.244(3) . ?
C3 N6 1.322(3) . ?
C3 N7 1.377(3) . ?
C3 N10 1.390(3) . ?
O3 N9 1.274(2) . ?
N5 N6 1.404(3) . ?
N8 H8A 0.8800 . ?
N8 H8B 0.8800 . ?
N9 N10 1.301(3) . ?
N12 H12A 0.8830 . ?
N12 H12B 0.8830 . ?
N12 H12C 0.94(2) . ?
O4 H4 0.8400 . ?
O4 N11 1.406(3) . ?
N11 H11A 0.8881 . ?
N11 H11B 0.8877 . ?
N11 H11C 0.95(3) . ?
O5 H5A 0.8702 . ?
O5 H5B 0.8697 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C1 N4 113.4(2) . . ?
N3 C1 N5 124.2(2) . . ?
N4 C1 N5 122.5(2) . . ?
N2 N1 N4 110.40(18) . . ?
N12 O1 H1 109.5 . . ?
N7 C2 N5 109.40(19) . . ?
N7 C2 N8 126.5(2) . . ?
N8 C2 N5 124.1(2) . . ?
N1 N2 N3 109.31(19) . . ?
N6 C3 N7 115.7(2) . . ?
N6 C3 N10 130.4(2) . . ?
N7 C3 N10 113.8(2) . . ?
C1 N3 N2 104.07(19) . . ?
C1 N4 N1 102.9(2) . . ?
C1 N5 N6 120.37(18) . . ?
C2 N5 C1 129.04(19) . . ?
C2 N5 N6 110.02(18) . . ?
C3 N6 N5 101.21(19) . . ?
C2 N7 C3 103.63(19) . . ?
C2 N8 H8A 120.0 . . ?
C2 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
O2 N9 O3 119.0(2) . . ?
O2 N9 N10 124.57(19) . . ?
O3 N9 N10 116.41(18) . . ?
N9 N10 C3 117.8(2) . . ?
O1 N12 H12A 109.5 . . ?
O1 N12 H12B 110.1 . . ?
O1 N12 H12C 110(2) . . ?
H12A N12 H12B 109.1 . . ?
H12A N12 H12C 107.1 . . ?
H12B N12 H12C 111.1 . . ?
N11 O4 H4 109.5 . . ?
O4 N11 H11A 110.6 . . ?
O4 N11 H11B 110.2 . . ?
O4 N11 H11C 108.7(18) . . ?
H11A N11 H11B 108.7 . . ?
H11A N11 H11C 109.4 . . ?
H11B N11 H11C 109.2 . . ?
H5A O5 H5B 104.5 . . ?

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
O1 H1 N3 0.84 1.83 2.645(3) 164.2 .
N8 H8A O2 0.88 2.10 2.934(3) 156.9 2_464
N8 H8B N4 0.88 2.24 2.859(3) 126.9 .
N12 H12A N7 0.88 2.01 2.877(3) 165.3 2_665
N12 H12B O1 0.88 2.29 2.995(3) 136.9 1_455
N12 H12C O2 0.94(2) 2.10(3) 2.696(3) 120(2) .
N12 H12C N6 0.94(2) 1.99(2) 2.890(3) 161(3) .
O4 H4 O5 0.84 1.77 2.596(3) 169.7 .
N11 H11A N1 0.89 1.99 2.847(3) 163.0 3_445
N11 H11B O3 0.89 1.88 2.733(3) 159.9 .
N11 H11C O1 0.95(3) 2.18(3) 2.940(3) 136(2) 2_464
O5 H5A N2 0.87 2.01 2.872(3) 168.8 2_464
O5 H5B N4 0.87 2.10 2.902(3) 152.7 3_445

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
C1 N5 N6 C3 -172.88(19) . . . . ?
N1 N2 N3 C1 0.1(2) . . . . ?
C2 N5 N6 C3 -0.8(2) . . . . ?
N2 N1 N4 C1 0.2(2) . . . . ?
O2 N9 N10 C3 2.1(3) . . . . ?
N3 C1 N4 N1 -0.2(2) . . . . ?
N3 C1 N5 C2 -176.2(2) . . . . ?
N3 C1 N5 N6 -5.7(3) . . . . ?
O3 N9 N10 C3 -177.2(2) . . . . ?
N4 C1 N3 N2 0.1(3) . . . . ?
N4 C1 N5 C2 3.2(3) . . . . ?
N4 C1 N5 N6 173.6(2) . . . . ?
N4 N1 N2 N3 -0.2(2) . . . . ?
N5 C1 N3 N2 179.52(19) . . . . ?
N5 C1 N4 N1 -179.64(19) . . . . ?
N5 C2 N7 C3 -0.5(2) . . . . ?
N6 C3 N7 C2 0.0(3) . . . . ?
N6 C3 N10 N9 0.9(4) . . . . ?
N7 C2 N5 C1 172.1(2) . . . . ?
N7 C2 N5 N6 0.9(3) . . . . ?
N7 C3 N6 N5 0.5(3) . . . . ?
N7 C3 N10 N9 177.54(18) . . . . ?
N8 C2 N5 C1 -9.3(4) . . . . ?
N8 C2 N5 N6 179.5(2) . . . . ?
N8 C2 N7 C3 -179.1(2) . . . . ?
N10 C3 N6 N5 177.1(2) . . . . ?
N10 C3 N7 C2 -177.14(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
