# Electronic Supplementary Material (ESI) for Analytical Methods.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_skkar38
_database_code_depnum_ccdc_archive 'CCDC 2075677'
loop_
_audit_author_name
_audit_author_address
'Atanu Jana'
;Dongguk University
South Korea
;
_audit_update_record             
;
2021-04-05 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H28 Cu2 N12 O12'
_chemical_formula_weight         923.76

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4663(13)
_cell_length_b                   9.2044(14)
_cell_length_c                   11.8424(18)
_cell_angle_alpha                73.774(2)
_cell_angle_beta                 70.534(2)
_cell_angle_gamma                80.563(2)
_cell_volume                     832.9(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5806
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      27.88

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             470
_exptl_absorpt_coefficient_mu    1.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6844
_exptl_absorpt_correction_T_max  0.8753
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9623
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         27.97
_reflns_number_total             3719
_reflns_number_gt                3071
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0859P)²+1.2631P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3719
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1653
_refine_ls_wR_factor_gt          0.1501
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7804(5) 0.3141(4) 0.1373(4) 0.0183(8) Uani 1 1 d . . .
H1 H 0.8381 0.3518 0.0525 0.022 Uiso 1 1 calc R . .
C2 C 0.8405(5) 0.1774(5) 0.2016(4) 0.0216(9) Uani 1 1 d . . .
H2 H 0.9387 0.1227 0.1617 0.026 Uiso 1 1 calc R . .
C3 C 0.7553(6) 0.1230(4) 0.3243(4) 0.0224(9) Uani 1 1 d . . .
H3 H 0.7943 0.0294 0.3694 0.027 Uiso 1 1 calc R . .
C4 C 0.6122(5) 0.2043(5) 0.3825(4) 0.0202(8) Uani 1 1 d . . .
H4 H 0.5507 0.1676 0.4667 0.024 Uiso 1 1 calc R . .
C5 C 0.5636(5) 0.3407(4) 0.3124(4) 0.0176(8) Uani 1 1 d . . .
C6 C 0.3174(5) 0.4436(5) 0.4755(4) 0.0206(8) Uani 1 1 d . . .
C7 C 0.2002(5) 0.5650(5) 0.4593(4) 0.0205(8) Uani 1 1 d . . .
H7 H 0.1094 0.5981 0.5219 0.025 Uiso 1 1 calc R . .
C8 C 0.2427(5) 0.6297(4) 0.3313(4) 0.0176(8) Uani 1 1 d . . .
C9 C 0.1504(5) 0.7540(4) 0.2632(4) 0.0176(8) Uani 1 1 d . . .
C10 C 0.4170(5) 0.8651(4) -0.0436(4) 0.0170(8) Uani 1 1 d . . .
H10A H 0.3437 0.9539 -0.0561 0.020 Uiso 1 1 calc R . .
C11 C 0.5686(5) 0.8513(4) -0.1443(4) 0.0185(8) Uani 1 1 d . . .
C12 C 0.5980(5) 0.9776(4) -0.2470(4) 0.0208(8) Uani 1 1 d . . .
H12 H 0.5225 1.0661 -0.2445 0.025 Uiso 1 1 calc R . .
C13 C 0.7333(5) 0.9751(5) -0.3504(4) 0.0214(8) Uani 1 1 d . . .
H13 H 0.7513 1.0612 -0.4185 0.026 Uiso 1 1 calc R . .
C14 C 0.8447(5) 0.8449(5) -0.3548(4) 0.0205(8) Uani 1 1 d . . .
H14 H 0.9377 0.8420 -0.4266 0.025 Uiso 1 1 calc R . .
C15 C 0.8192(5) 0.7207(4) -0.2548(4) 0.0184(8) Uani 1 1 d . . .
C16 C 0.6803(5) 0.7192(4) -0.1470(4) 0.0160(8) Uani 1 1 d . . .
C28 C 0.3333(5) 0.3385(5) 0.5937(4) 0.0226(9) Uani 1 1 d . . .
H28A H 0.2996 0.2385 0.6013 0.034 Uiso 1 1 calc R . .
H28B H 0.2605 0.3793 0.6634 0.034 Uiso 1 1 calc R . .
H28C H 0.4502 0.3290 0.5939 0.034 Uiso 1 1 calc R . .
N1 N 0.6424(4) 0.3942(4) 0.1925(3) 0.0167(7) Uani 1 1 d . . .
N2 N 0.4215(4) 0.4377(4) 0.3589(3) 0.0174(7) Uani 1 1 d . . .
N3 N 0.3775(4) 0.5520(4) 0.2723(3) 0.0163(7) Uani 1 1 d . . .
N4 N 0.2138(5) 0.8041(4) 0.1387(3) 0.0203(7) Uani 1 1 d . . .
N5 N 0.3721(4) 0.7679(4) 0.0617(3) 0.0172(7) Uani 1 1 d . . .
N6 N 0.8347(4) 0.7569(4) 0.0975(3) 0.0182(7) Uani 1 1 d . . .
O1 O 0.0128(4) 0.8070(3) 0.3193(3) 0.0240(7) Uani 1 1 d . . .
O2 O 0.9333(4) 0.5964(3) -0.2628(3) 0.0220(6) Uani 1 1 d . . .
O3 O 0.6632(4) 0.5919(3) -0.0584(2) 0.0176(6) Uani 1 1 d . . .
O4 O 0.6766(3) 0.7654(3) 0.1243(3) 0.0198(6) Uani 1 1 d . . .
O5 O 0.9148(4) 0.6293(3) 0.1132(3) 0.0260(7) Uani 1 1 d . . .
O6 O 0.9092(4) 0.8760(3) 0.0558(3) 0.0237(6) Uani 1 1 d . . .
Cu1 Cu 0.52495(6) 0.58457(5) 0.10596(4) 0.01635(18) Uani 1 1 d . . .
H2O H 0.915(7) 0.537(7) -0.191(6) 0.040(16) Uiso 1 1 d . . .
H4N H 0.154(7) 0.857(7) 0.108(5) 0.033(15) 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
C1 N1 1.347(5) . ?
C1 C2 1.391(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.376(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.338(5) . ?
C5 N2 1.424(5) . ?
C6 N2 1.379(5) . ?
C6 C7 1.383(6) . ?
C6 C28 1.497(6) . ?
C7 C8 1.409(6) . ?
C7 H7 0.9500 . ?
C8 N3 1.335(5) . ?
C8 C9 1.477(5) . ?
C9 O1 1.231(5) . ?
C9 N4 1.360(5) . ?
C10 N5 1.294(5) . ?
C10 C11 1.448(6) . ?
C10 H10A 0.9500 . ?
C11 C12 1.413(6) . ?
C11 C16 1.413(5) . ?
C12 C13 1.372(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(6) . ?
C14 H14 0.9500 . ?
C15 O2 1.374(5) . ?
C15 C16 1.417(6) . ?
C16 O3 1.328(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N1 Cu1 2.052(3) . ?
N2 N3 1.349(5) . ?
N3 Cu1 1.919(3) . ?
N4 N5 1.396(5) . ?
N4 H4N 0.75(6) . ?
N5 Cu1 2.010(3) . ?
N6 O6 1.248(4) . ?
N6 O5 1.255(4) . ?
N6 O4 1.262(4) . ?
O2 H2O 0.85(6) . ?
O3 Cu1 1.897(3) . ?
O4 Cu1 2.357(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.6(4) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 118.8(4) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 117.0(4) . . ?
C5 C4 H4 121.5 . . ?
C3 C4 H4 121.5 . . ?
N1 C5 C4 123.7(4) . . ?
N1 C5 N2 112.5(3) . . ?
C4 C5 N2 123.8(4) . . ?
N2 C6 C7 106.1(4) . . ?
N2 C6 C28 125.6(4) . . ?
C7 C6 C28 128.3(4) . . ?
C6 C7 C8 106.1(4) . . ?
C6 C7 H7 126.9 . . ?
C8 C7 H7 126.9 . . ?
N3 C8 C7 109.9(3) . . ?
N3 C8 C9 121.4(4) . . ?
C7 C8 C9 128.4(4) . . ?
O1 C9 N4 120.5(4) . . ?
O1 C9 C8 119.5(4) . . ?
N4 C9 C8 120.0(3) . . ?
N5 C10 C11 126.1(3) . . ?
N5 C10 H10A 116.9 . . ?
C11 C10 H10A 116.9 . . ?
C12 C11 C16 119.8(4) . . ?
C12 C11 C10 116.0(3) . . ?
C16 C11 C10 124.1(4) . . ?
C13 C12 C11 121.3(4) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 119.6(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
O2 C15 C14 117.8(4) . . ?
O2 C15 C16 120.3(3) . . ?
C14 C15 C16 121.9(4) . . ?
O3 C16 C11 125.4(4) . . ?
O3 C16 C15 117.1(3) . . ?
C11 C16 C15 117.4(4) . . ?
C6 C28 H28A 109.5 . . ?
C6 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C6 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C5 N1 C1 118.6(3) . . ?
C5 N1 Cu1 115.3(3) . . ?
C1 N1 Cu1 125.9(3) . . ?
N3 N2 C6 110.9(3) . . ?
N3 N2 C5 115.0(3) . . ?
C6 N2 C5 134.1(3) . . ?
C8 N3 N2 107.0(3) . . ?
C8 N3 Cu1 134.4(3) . . ?
N2 N3 Cu1 118.1(3) . . ?
C9 N4 N5 128.5(3) . . ?
C9 N4 H4N 115(4) . . ?
N5 N4 H4N 117(4) . . ?
C10 N5 N4 114.2(3) . . ?
C10 N5 Cu1 121.0(3) . . ?
N4 N5 Cu1 124.8(3) . . ?
O6 N6 O5 120.8(3) . . ?
O6 N6 O4 119.4(3) . . ?
O5 N6 O4 119.7(3) . . ?
C15 O2 H2O 108(4) . . ?
C16 O3 Cu1 122.6(2) . . ?
N6 O4 Cu1 124.3(2) . . ?
O3 Cu1 N3 172.52(13) . . ?
O3 Cu1 N5 95.49(12) . . ?
N3 Cu1 N5 87.98(13) . . ?
O3 Cu1 N1 98.07(12) . . ?
N3 Cu1 N1 78.44(13) . . ?
N5 Cu1 N1 166.41(14) . . ?
O3 Cu1 O4 91.58(11) . . ?
N3 Cu1 O4 95.42(12) . . ?
N5 Cu1 O4 83.01(12) . . ?
N1 Cu1 O4 97.53(12) . . ?

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
O2 H2O O5 0.85(6) 2.15(6) 2.774(4) 129(5) 2_765
O2 H2O O3 0.85(6) 2.27(6) 2.716(4) 113(5) .
N4 H4N O6 0.75(6) 2.32(6) 2.969(5) 145(5) 1_455

_diffrn_measured_fraction_theta_max 0.929
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.503
_refine_diff_density_min         -1.130
_refine_diff_density_rms         0.155
