# Supplementary Information (SI) for RSC Advances.
# 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_amide2cu
_database_code_depnum_ccdc_archive 'CCDC 2388873'
loop_
_audit_author_name
_audit_author_address
'Swaraj Sengupta'
;Birla Institute of Technology, Mesra, Ranchi, India
Iceland
;
_audit_update_record             
;
2024-10-05 deposited with the CCDC.	2025-11-05 downloaded from the CCDC.
;
_audit_creation_date             2023-01-19
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 Cu N3 O4, 2(H2 O)'
_chemical_formula_sum            'C13 H15 Cu N3 O6'
_chemical_formula_weight         372.82
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H7 Cu1 N3 O3 '
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'
Cu Cu 0.3201 1.2651 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.5673(3)
_cell_length_b                   10.4935(4)
_cell_length_c                   16.3022(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.043(3)
_cell_angle_gamma                90
_cell_volume                     1454.52(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3963
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.1640
_cell_measurement_theta_min      3.7660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.538
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5941
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.440
_diffrn_ambient_temperature      298.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4324
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  79.00   1.00  140.15    --   10.07  77.00 120.00   98
  2  ω    -38.00  30.00   1.00  140.15    --   10.07 -38.00 -30.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0243745000
_diffrn_orient_matrix_UB_12      -0.0112009000
_diffrn_orient_matrix_UB_13      -0.0394191000
_diffrn_orient_matrix_UB_21      0.0019069000
_diffrn_orient_matrix_UB_22      -0.0664389000
_diffrn_orient_matrix_UB_23      0.0079771000
_diffrn_orient_matrix_UB_31      -0.0797471000
_diffrn_orient_matrix_UB_32      -0.0050452000
_diffrn_orient_matrix_UB_33      -0.0175205000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2282
_reflns_number_total             2540
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2540
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.045
_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)+(0.0385P)²+0.5895P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0755
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B), O6(H6A,H6B)
2.b Rotating group:
 O4(H4A)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.d Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C3(H3), C10(H10), C13(H13), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.34936(3) 0.20788(2) 0.46347(2) 0.02933(12) Uani 1 1 d . . . . .
O4 O 0.4828(2) 0.10549(17) 0.40020(14) 0.0385(4) Uani 1 1 d . . . . .
H4A H 0.474036 0.026403 0.411894 0.058 Uiso 1 1 d GR . . . .
O3 O 0.14771(18) 0.45863(16) 0.61466(11) 0.0387(4) Uani 1 1 d . . . . .
O2 O 0.5659(2) 0.16748(17) 0.69966(12) 0.0502(5) Uani 1 1 d . . . . .
N1 N 0.2131(2) 0.29872(17) 0.53061(12) 0.0288(4) Uani 1 1 d . . . . .
O5 O 0.5572(2) 0.1756(2) 0.25388(13) 0.0522(5) Uani 1 1 d . . . . .
H5A H 0.635625 0.224072 0.267339 0.078 Uiso 1 1 d G . . . .
H5B H 0.576475 0.127088 0.214559 0.078 Uiso 1 1 d G . . . .
N2 N 0.1452(2) 0.12890(18) 0.41428(12) 0.0319(4) Uani 1 1 d . . . . .
O6 O 0.1864(3) 0.6739(2) 0.70768(16) 0.0646(6) Uani 1 1 d . . . . .
H6A H 0.100610 0.684971 0.727895 0.097 Uiso 1 1 d G . . . .
H6B H 0.179844 0.607028 0.678057 0.097 Uiso 1 1 d G . . . .
C6 C 0.4159(2) 0.4369(2) 0.59656(13) 0.0253(5) Uani 1 1 d . . . . .
C7 C 0.2468(2) 0.3955(2) 0.58062(14) 0.0268(5) Uani 1 1 d . . . . .
C1 C 0.5328(3) 0.2144(2) 0.63107(15) 0.0310(5) Uani 1 1 d . . . . .
C5 C 0.4471(2) 0.5662(2) 0.58733(13) 0.0259(5) Uani 1 1 d . . . . .
H5 H 0.362259 0.620269 0.572681 0.031 Uiso 1 1 calc R . . . .
C2 C 0.5433(3) 0.3571(2) 0.62167(13) 0.0275(5) Uani 1 1 d . . . . .
C9 C 0.0201(3) 0.1634(2) 0.45114(15) 0.0313(5) Uani 1 1 d . . . . .
C4 C 0.7100(3) 0.5401(2) 0.62613(15) 0.0353(6) Uani 1 1 d . . . . .
H4 H 0.810186 0.574907 0.637021 0.042 Uiso 1 1 calc R . . . .
C3 C 0.6911(3) 0.4121(2) 0.63942(15) 0.0346(6) Uani 1 1 d . . . . .
H3 H 0.776815 0.362402 0.660208 0.041 Uiso 1 1 calc R . . . .
C8 C 0.0447(3) 0.2686(2) 0.51329(17) 0.0347(6) Uani 1 1 d . . . . .
H8A H -0.012651 0.343792 0.492166 0.042 Uiso 1 1 calc R . . . .
H8B H 0.004811 0.242955 0.563945 0.042 Uiso 1 1 calc R . . . .
C10 C -0.1250(3) 0.1053(2) 0.43158(18) 0.0406(6) Uani 1 1 d . . . . .
H10 H -0.209875 0.128326 0.458912 0.049 Uiso 1 1 calc R . . . .
C13 C 0.1275(3) 0.0383(3) 0.35522(16) 0.0420(6) Uani 1 1 d . . . . .
H13 H 0.214106 0.014355 0.329589 0.050 Uiso 1 1 calc R . . . .
C11 C -0.1415(3) 0.0135(3) 0.37140(18) 0.0450(7) Uani 1 1 d . . . . .
H11 H -0.238086 -0.026250 0.357352 0.054 Uiso 1 1 calc R . . . .
C12 C -0.0145(3) -0.0195(3) 0.33184(18) 0.0487(7) Uani 1 1 d . . . . .
H12 H -0.024727 -0.080054 0.289892 0.058 Uiso 1 1 calc R . . . .
O1 O 0.4983(2) 0.15057(15) 0.56486(11) 0.0398(4) Uani 1 1 d . . . . .
N3 N 0.5901(2) 0.61707(17) 0.59811(12) 0.0299(4) Uani 1 1 d . . . . .
H4B H 0.493(3) 0.124(3) 0.3582(19) 0.040(10) 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
Cu1 O4 1.9530(18) . ?
Cu1 N1 1.9447(19) . ?
Cu1 N2 2.0111(18) . ?
Cu1 O1 2.0507(17) . ?
Cu1 N3 2.1860(19) 3_666 ?
O3 C7 1.258(3) . ?
O2 C1 1.223(3) . ?
N1 C7 1.312(3) . ?
N1 C8 1.470(3) . ?
N2 C9 1.342(3) . ?
N2 C13 1.348(3) . ?
C6 C7 1.505(3) . ?
C6 C5 1.394(3) . ?
C6 C2 1.396(3) . ?
C1 C2 1.509(3) . ?
C1 O1 1.274(3) . ?
C5 N3 1.329(3) . ?
C2 C3 1.389(3) . ?
C9 C8 1.496(3) . ?
C9 C10 1.386(3) . ?
C4 C3 1.373(3) . ?
C4 N3 1.342(3) . ?
C10 C11 1.370(4) . ?
C13 C12 1.370(4) . ?
C11 C12 1.376(4) . ?

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
O4 Cu1 N2 95.70(8) . . ?
O4 Cu1 O1 85.27(8) . . ?
O4 Cu1 N3 91.86(8) . 3_666 ?
N1 Cu1 O4 175.89(8) . . ?
N1 Cu1 N2 82.75(8) . . ?
N1 Cu1 O1 92.71(8) . . ?
N1 Cu1 N3 92.24(7) . 3_666 ?
N2 Cu1 O1 128.72(8) . . ?
N2 Cu1 N3 114.00(8) . 3_666 ?
O1 Cu1 N3 117.22(7) . 3_666 ?
C7 N1 Cu1 128.89(15) . . ?
C7 N1 C8 114.91(19) . . ?
C8 N1 Cu1 115.42(14) . . ?
C9 N2 Cu1 114.45(15) . . ?
C9 N2 C13 118.9(2) . . ?
C13 N2 Cu1 126.29(16) . . ?
C5 C6 C7 117.08(19) . . ?
C5 C6 C2 117.5(2) . . ?
C2 C6 C7 125.4(2) . . ?
O3 C7 N1 125.0(2) . . ?
O3 C7 C6 117.36(19) . . ?
N1 C7 C6 117.66(19) . . ?
O2 C1 C2 118.8(2) . . ?
O2 C1 O1 124.6(2) . . ?
O1 C1 C2 116.5(2) . . ?
N3 C5 C6 124.2(2) . . ?
C6 C2 C1 124.8(2) . . ?
C3 C2 C6 118.1(2) . . ?
C3 C2 C1 117.07(19) . . ?
N2 C9 C8 116.63(19) . . ?
N2 C9 C10 121.4(2) . . ?
C10 C9 C8 121.9(2) . . ?
N3 C4 C3 122.9(2) . . ?
C4 C3 C2 119.7(2) . . ?
N1 C8 C9 110.03(19) . . ?
C11 C10 C9 119.0(3) . . ?
N2 C13 C12 122.0(2) . . ?
C10 C11 C12 119.6(2) . . ?
C13 C12 C11 119.0(3) . . ?
C1 O1 Cu1 125.84(14) . . ?
C5 N3 Cu1 122.95(15) . 3_666 ?
C5 N3 C4 117.25(19) . . ?
C4 N3 Cu1 116.59(15) . 3_666 ?

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
Cu1 N1 C7 O3 171.29(17) . . . . ?
Cu1 N1 C7 C6 -6.8(3) . . . . ?
Cu1 N1 C8 C9 5.1(3) . . . . ?
Cu1 N2 C9 C8 9.1(3) . . . . ?
Cu1 N2 C9 C10 -171.72(19) . . . . ?
Cu1 N2 C13 C12 172.9(2) . . . . ?
O2 C1 C2 C6 -116.4(3) . . . . ?
O2 C1 C2 C3 63.7(3) . . . . ?
O2 C1 O1 Cu1 149.4(2) . . . . ?
N2 C9 C8 N1 -9.2(3) . . . . ?
N2 C9 C10 C11 -2.1(4) . . . . ?
N2 C13 C12 C11 -1.8(4) . . . . ?
C6 C5 N3 Cu1 153.42(17) . . . 3_666 ?
C6 C5 N3 C4 -5.6(3) . . . . ?
C6 C2 C3 C4 -4.8(3) . . . . ?
C7 N1 C8 C9 175.9(2) . . . . ?
C7 C6 C5 N3 -179.1(2) . . . . ?
C7 C6 C2 C1 4.6(3) . . . . ?
C7 C6 C2 C3 -175.5(2) . . . . ?
C1 C2 C3 C4 175.2(2) . . . . ?
C5 C6 C7 O3 -48.4(3) . . . . ?
C5 C6 C7 N1 129.8(2) . . . . ?
C5 C6 C2 C1 -177.1(2) . . . . ?
C5 C6 C2 C3 2.9(3) . . . . ?
C2 C6 C7 O3 130.0(2) . . . . ?
C2 C6 C7 N1 -51.8(3) . . . . ?
C2 C6 C5 N3 2.4(3) . . . . ?
C2 C1 O1 Cu1 -34.9(3) . . . . ?
C9 N2 C13 C12 0.0(4) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C3 C4 N3 Cu1 -156.8(2) . . . 3_666 ?
C3 C4 N3 C5 3.5(3) . . . . ?
C8 N1 C7 O3 2.0(3) . . . . ?
C8 N1 C7 C6 -176.07(19) . . . . ?
C8 C9 C10 C11 177.0(2) . . . . ?
C10 C9 C8 N1 171.6(2) . . . . ?
C10 C11 C12 C13 1.7(4) . . . . ?
C13 N2 C9 C8 -177.2(2) . . . . ?
C13 N2 C9 C10 2.0(4) . . . . ?
O1 C1 C2 C6 67.7(3) . . . . ?
O1 C1 C2 C3 -112.3(2) . . . . ?
N3 C4 C3 C2 1.6(4) . . . . ?

_olex2_date_sample_data_collection 2022-07-07
_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 1.059
_oxdiff_exptl_absorpt_empirical_full_min 0.941
####################################################################### 
# 
# 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_snad1
_database_code_depnum_ccdc_archive 'CCDC 2388874'
loop_
_audit_author_name
_audit_author_address
'Swaraj Sengupta'
;Birla Institute of Technology, Mesra, Ranchi, India
India
;
_audit_update_record             
;
2024-10-05 deposited with the CCDC.	2025-11-05 downloaded from the CCDC.
;
_audit_creation_date             2024-07-30
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N3 O3, 2(H2 O)'
_chemical_formula_sum            'C13 H15 N3 O5'
_chemical_formula_weight         293.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H10 N4 O3'
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                   8.3624(6)
_cell_length_b                   8.5232(8)
_cell_length_c                   9.6931(8)
_cell_angle_alpha                92.749(7)
_cell_angle_beta                 92.290(6)
_cell_angle_gamma                96.721(7)
_cell_volume                     684.61(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2280
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7380
_cell_measurement_theta_min      4.2350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5220
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         3.308
_diffrn_ambient_temperature      298.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4324
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  37.00   1.00   62.21    --   10.07 -57.00 -30.00   97
  2  ω     -7.00  21.00   1.00   62.21    --   10.07  38.00   0.00   28
  3  ω    -38.00  30.00   1.00   62.21    --   10.07 -57.00-150.00   68
  4  ω    -86.00 -24.00   1.00   62.21    --  -10.22 166.00  -1.00   62
  5  ω    -18.00  29.00   1.00   62.21    --  -10.22 -99.00  90.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0074217000
_diffrn_orient_matrix_UB_12      -0.0165249000
_diffrn_orient_matrix_UB_13      0.0706382000
_diffrn_orient_matrix_UB_21      0.0115491000
_diffrn_orient_matrix_UB_22      -0.0798981000
_diffrn_orient_matrix_UB_23      -0.0158021000
_diffrn_orient_matrix_UB_31      0.0843876000
_diffrn_orient_matrix_UB_32      0.0196141000
_diffrn_orient_matrix_UB_33      0.0117890000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1767
_reflns_number_total             2396
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2396
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.023
_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)+(0.0677P)²+0.0821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1333
_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 O(H,H) groups
2.a Free rotating group:
 O4(H4A,H4B), O5(H5A,H5B)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C10(H10), C5(H5), C1(H1), C13(H13), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.21883(15) 0.13201(17) 0.40047(15) 0.0500(4) Uani 1 1 d . . . . .
O1 O -0.03128(16) 0.10575(18) 0.31349(15) 0.0527(4) Uani 1 1 d . . . . .
O3 O 0.41479(16) 0.34591(17) 0.63038(16) 0.0557(4) Uani 1 1 d . . . . .
N2 N 0.31187(17) 0.10904(18) 0.69612(17) 0.0394(4) Uani 1 1 d . . . . .
H2 H 0.229763 0.052760 0.726296 0.047 Uiso 1 1 calc R . . . .
N3 N 0.72431(18) 0.0529(2) 0.80873(17) 0.0396(4) Uani 1 1 d . . . . .
O4 O 0.5071(2) 0.66313(19) 0.6851(2) 0.0718(5) Uani 1 1 d . . . . .
H4A H 0.570078 0.697554 0.623715 0.108 Uiso 1 1 d G . . . .
H4B H 0.479617 0.564507 0.669220 0.108 Uiso 1 1 d G . . . .
N1 N -0.0681(2) 0.4406(2) 0.7442(2) 0.0580(5) Uani 1 1 d . . . . .
C6 C 0.0732(2) 0.1560(2) 0.4034(2) 0.0369(5) Uani 1 1 d . . . . .
C4 C 0.1300(2) 0.2967(2) 0.6394(2) 0.0373(5) Uani 1 1 d . . . . .
C3 C 0.0261(2) 0.2547(2) 0.5250(2) 0.0358(5) Uani 1 1 d . . . . .
C7 C 0.2970(2) 0.2519(2) 0.6526(2) 0.0381(5) Uani 1 1 d . . . . .
C9 C 0.5788(2) 0.1029(2) 0.81343(19) 0.0365(5) Uani 1 1 d . . . . .
C8 C 0.4655(2) 0.0476(3) 0.6930(2) 0.0445(5) Uani 1 1 d . . . . .
H8A H 0.516614 0.078126 0.608657 0.053 Uiso 1 1 calc R . . . .
H8B H 0.446737 -0.066994 0.689781 0.053 Uiso 1 1 calc R . . . .
C2 C -0.1239(2) 0.3071(2) 0.5246(2) 0.0450(5) Uani 1 1 d . . . . .
H2A H -0.196674 0.280145 0.449826 0.054 Uiso 1 1 calc R . . . .
O5 O -0.2447(3) 0.6516(3) 0.9183(2) 0.1066(8) Uani 1 1 d . . . . .
H5A H -0.323296 0.654760 0.860569 0.160 Uiso 1 1 d G . . . .
H5B H -0.179127 0.592748 0.884548 0.160 Uiso 1 1 d G . . . .
C10 C 0.5455(2) 0.1980(3) 0.9242(2) 0.0469(5) Uani 1 1 d . . . . .
H10 H 0.444913 0.233676 0.929621 0.056 Uiso 1 1 calc R . . . .
C5 C 0.0769(2) 0.3892(3) 0.7459(2) 0.0484(5) Uani 1 1 d . . . . .
H5 H 0.146163 0.416946 0.822858 0.058 Uiso 1 1 calc R . . . .
C1 C -0.1654(3) 0.3984(3) 0.6338(2) 0.0526(6) Uani 1 1 d . . . . .
H1 H -0.266892 0.432808 0.630766 0.063 Uiso 1 1 calc R . . . .
C13 C 0.8390(3) 0.0938(3) 0.9078(2) 0.0525(6) Uani 1 1 d . . . . .
H13 H 0.939151 0.057453 0.900731 0.063 Uiso 1 1 calc R . . . .
C11 C 0.6626(3) 0.2399(3) 1.0268(2) 0.0576(6) Uani 1 1 d . . . . .
H11 H 0.641200 0.304133 1.102463 0.069 Uiso 1 1 calc R . . . .
C12 C 0.8109(3) 0.1875(3) 1.0184(2) 0.0583(6) Uani 1 1 d . . . . .
H12 H 0.890746 0.216031 1.087578 0.070 Uiso 1 1 calc R . . . .
H3 H 0.750(3) -0.019(3) 0.729(3) 0.072(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C6 1.260(2) . ?
O1 C6 1.234(2) . ?
O3 C7 1.228(2) . ?
N2 H2 0.8600 . ?
N2 C7 1.325(2) . ?
N2 C8 1.443(2) . ?
N3 C9 1.337(2) . ?
N3 C13 1.335(3) . ?
N3 H3 1.00(3) . ?
O4 H4A 0.8501 . ?
O4 H4B 0.8501 . ?
N1 C5 1.337(3) . ?
N1 C1 1.327(3) . ?
C6 C3 1.507(3) . ?
C4 C3 1.387(3) . ?
C4 C7 1.493(3) . ?
C4 C5 1.387(3) . ?
C3 C2 1.380(3) . ?
C9 C8 1.496(3) . ?
C9 C10 1.371(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C2 H2A 0.9300 . ?
C2 C1 1.364(3) . ?
O5 H5A 0.8497 . ?
O5 H5B 0.8500 . ?
C10 H10 0.9300 . ?
C10 C11 1.372(3) . ?
C5 H5 0.9300 . ?
C1 H1 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.351(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(3) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N2 H2 119.9 . . ?
C7 N2 C8 120.19(17) . . ?
C8 N2 H2 119.9 . . ?
C9 N3 H3 120.0(14) . . ?
C13 N3 C9 122.12(17) . . ?
C13 N3 H3 117.9(14) . . ?
H4A O4 H4B 109.5 . . ?
C1 N1 C5 117.05(18) . . ?
O2 C6 C3 116.93(16) . . ?
O1 C6 O2 124.44(18) . . ?
O1 C6 C3 118.63(17) . . ?
C3 C4 C7 123.77(17) . . ?
C3 C4 C5 118.02(18) . . ?
C5 C4 C7 118.19(17) . . ?
C4 C3 C6 122.03(16) . . ?
C2 C3 C6 120.09(17) . . ?
C2 C3 C4 117.88(18) . . ?
O3 C7 N2 121.90(18) . . ?
O3 C7 C4 121.34(18) . . ?
N2 C7 C4 116.68(17) . . ?
N3 C9 C8 115.13(16) . . ?
N3 C9 C10 119.09(17) . . ?
C10 C9 C8 125.79(17) . . ?
N2 C8 C9 114.45(16) . . ?
N2 C8 H8A 108.6 . . ?
N2 C8 H8B 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 C3 120.01(19) . . ?
C1 C2 H2A 120.0 . . ?
H5A O5 H5B 109.5 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.12(19) . . ?
C11 C10 H10 120.4 . . ?
N1 C5 C4 123.75(19) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
N1 C1 C2 123.28(19) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
N3 C13 H13 119.7 . . ?
N3 C13 C12 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 118.79(19) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?

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 C6 C3 C4 -10.0(3) . . . . ?
O2 C6 C3 C2 169.62(18) . . . . ?
O1 C6 C3 C4 170.74(17) . . . . ?
O1 C6 C3 C2 -9.7(3) . . . . ?
N3 C9 C8 N2 -177.01(16) . . . . ?
N3 C9 C10 C11 0.3(3) . . . . ?
N3 C13 C12 C11 -0.1(4) . . . . ?
C6 C3 C2 C1 -179.00(18) . . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C3 C4 C7 O3 100.2(2) . . . . ?
C3 C4 C7 N2 -83.1(2) . . . . ?
C3 C4 C5 N1 -0.4(3) . . . . ?
C3 C2 C1 N1 -0.4(3) . . . . ?
C7 N2 C8 C9 82.2(2) . . . . ?
C7 C4 C3 C6 1.1(3) . . . . ?
C7 C4 C3 C2 -178.47(18) . . . . ?
C7 C4 C5 N1 178.0(2) . . . . ?
C9 N3 C13 C12 0.5(3) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C8 N2 C7 O3 -12.2(3) . . . . ?
C8 N2 C7 C4 171.10(15) . . . . ?
C8 C9 C10 C11 -179.5(2) . . . . ?
C10 C9 C8 N2 2.8(3) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C5 N1 C1 C2 -0.2(3) . . . . ?
C5 C4 C3 C6 179.36(17) . . . . ?
C5 C4 C3 C2 -0.2(3) . . . . ?
C5 C4 C7 O3 -78.1(3) . . . . ?
C5 C4 C7 N2 98.6(2) . . . . ?
C1 N1 C5 C4 0.6(3) . . . . ?
C13 N3 C9 C8 179.22(18) . . . . ?
C13 N3 C9 C10 -0.6(3) . . . . ?

_olex2_date_sample_data_collection 2022-02-03
_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 1.483
_oxdiff_exptl_absorpt_empirical_full_min 0.732
