# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_cupapy
_database_code_depnum_ccdc_archive 'CCDC 2068506'
loop_
_audit_author_name
_audit_author_address
'Mainak Mitra'
;Burdwan Raj College
India
;
_audit_update_record             
;
2021-03-07 deposited with the CCDC.	2021-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H28 Cu2 N4 O6, 2 (C H4 O)'
_chemical_formula_sum            'C32 H36 Cu2 N4 O8'
_chemical_formula_weight         731.73

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5547(3)
_cell_length_b                   9.8407(4)
_cell_length_c                   10.2731(4)
_cell_angle_alpha                113.7330(10)
_cell_angle_beta                 99.453(2)
_cell_angle_gamma                92.307(2)
_cell_volume                     775.51(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    14160
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      29.13

_exptl_crystal_description       needle
_exptl_crystal_colour            'bluish green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_F_000             378
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.537
_exptl_crystal_size_mid          0.339
_exptl_crystal_size_min          0.335
_exptl_absorpt_coefficient_mu    1.430
_shelx_estimated_absorpt_T_min   0.514
_shelx_estimated_absorpt_T_max   0.646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6281
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  'Bruker KAPPA APEX II CCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_detector_area_resol_mean 16
_diffrn_reflns_number            10178
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.945
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3323
_reflns_number_gt                3228
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2008)'
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
'CrystaMaker (CrystalMaker Software ltd., 2011)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0262P)²+0.7743P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3323
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0661
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_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_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 0.50368(2) 0.58689(2) 0.17046(2) 0.01119(7) Uani 1 1 d . . . . .
O1 O 0.45668(14) 0.42272(13) 0.22521(13) 0.0159(2) Uani 1 1 d . . . . .
O2 O 0.34227(15) 0.37013(14) 0.38195(14) 0.0216(3) Uani 1 1 d . . . . .
O3 O 0.66605(13) 0.50834(12) 0.05931(12) 0.0133(2) Uani 1 1 d . . . . .
N1 N 0.53778(15) 0.78912(15) 0.17107(14) 0.0125(3) Uani 1 1 d . . . . .
N2 N 0.32305(15) 0.67325(14) 0.27277(14) 0.0118(3) Uani 1 1 d . . . . .
C1 C 0.63871(19) 0.83142(18) 0.10296(17) 0.0152(3) Uani 1 1 d . . . . .
H1 H 0.6978 0.7594 0.0447 0.018 Uiso 1 1 calc R U . . .
C2 C 0.4604(2) 1.03566(18) 0.26220(18) 0.0174(3) Uani 1 1 d . . . . .
H2 H 0.3944 1.1038 0.3153 0.021 Uiso 1 1 calc R U . . .
C3 C 0.5674(2) 1.08025(19) 0.19529(19) 0.0200(3) Uani 1 1 d . . . . .
H3 H 0.5780 1.1802 0.2040 0.024 Uiso 1 1 calc R U . . .
C4 C 0.77214(18) 0.41788(17) 0.07576(17) 0.0123(3) Uani 1 1 d . . . . .
C5 C 0.45100(18) 0.88975(17) 0.25048(16) 0.0130(3) Uani 1 1 d . . . . .
C6 C 0.35215(19) 0.83850(17) 0.33487(17) 0.0148(3) Uani 1 1 d . . . . .
H6A H 0.4085 0.8766 0.4372 0.018 Uiso 1 1 calc R U . . .
H6B H 0.2488 0.8801 0.3330 0.018 Uiso 1 1 calc R U . . .
C7 C 0.3240(2) 0.61157(18) 0.38274(17) 0.0156(3) Uani 1 1 d . . . . .
H7A H 0.2158 0.6074 0.4046 0.019 Uiso 1 1 calc R U . . .
H7B H 0.3984 0.6774 0.4735 0.019 Uiso 1 1 calc R U . . .
C8 C 0.37588(19) 0.45446(18) 0.32588(17) 0.0150(3) Uani 1 1 d . . . . .
C9 C 0.83241(18) 0.38408(18) -0.16662(17) 0.0139(3) Uani 1 1 d . . . . .
H9A H 0.8467 0.4944 -0.1293 0.017 Uiso 1 1 calc R U . . .
H9B H 0.9195 0.3464 -0.2195 0.017 Uiso 1 1 calc R U . . .
C10 C 0.85137(18) 0.34350(17) -0.03934(17) 0.0134(3) Uani 1 1 d . . . . .
C11 C 0.96053(19) 0.24591(18) -0.02606(18) 0.0172(3) Uani 1 1 d . . . . .
H11 H 1.0097 0.1930 -0.1055 0.021 Uiso 1 1 calc R U . . .
C12 C 0.6590(2) 0.97662(19) 0.11521(18) 0.0193(3) Uani 1 1 d . . . . .
H12 H 0.7343 1.0050 0.0696 0.023 Uiso 1 1 calc R U . . .
C13 C 0.9262(2) 0.3028(2) 0.21583(19) 0.0197(3) Uani 1 1 d . . . . .
H13 H 0.9542 0.2919 0.3042 0.024 Uiso 1 1 calc R U . . .
C14 C 0.81335(19) 0.39694(19) 0.20402(18) 0.0166(3) Uani 1 1 d . . . . .
H14 H 0.7634 0.4477 0.2835 0.020 Uiso 1 1 calc R U . . .
C15 C 0.9991(2) 0.22425(19) 0.1004(2) 0.0208(3) Uani 1 1 d . . . . .
H15 H 1.0735 0.1574 0.1079 0.025 Uiso 1 1 calc R U . . .
O4 O 0.69541(16) 0.74762(18) 0.43214(15) 0.0291(3) Uani 1 1 d . . . . .
H4 H 0.6959 0.7038 0.4875 0.044 Uiso 1 1 calc R U . . .
C16 C 0.8529(2) 0.8036(3) 0.4407(2) 0.0342(5) Uani 1 1 d . . . . .
H16A H 0.8518 0.8587 0.3796 0.051 Uiso 1 1 calc R U . . .
H16B H 0.9168 0.7203 0.4070 0.051 Uiso 1 1 calc R U . . .
H16C H 0.8996 0.8708 0.5415 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O3 1.9307(11) . yes
Cu1 O1 1.9600(11) . yes
Cu1 N1 1.9970(13) . yes
Cu1 N2 2.0335(13) . yes
Cu1 O3 2.3542(11) 2_665 yes
O1 C8 1.279(2) . ?
O2 C8 1.234(2) . ?
O3 C4 1.3344(18) . ?
O3 Cu1 2.3542(11) 2_665 yes
N1 C5 1.344(2) . ?
N1 C1 1.346(2) . ?
N2 C6 1.4810(19) . ?
N2 C7 1.481(2) . ?
N2 C9 1.4980(19) 2_665 ?
C1 C12 1.384(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(2) . ?
C2 C5 1.390(2) . ?
C2 H2 0.9500 . ?
C3 C12 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C14 1.405(2) . ?
C4 C10 1.414(2) . ?
C5 C6 1.510(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.531(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 N2 1.4980(19) 2_665 ?
C9 C10 1.500(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.396(2) . ?
C11 C15 1.389(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 C15 1.392(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
O4 C16 1.410(2) . ?
O4 H4 0.8400 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
O3 Cu1 O1 99.82(5) . . ?
O3 Cu1 N1 94.05(5) . . ?
O1 Cu1 N1 163.38(5) . . ?
O3 Cu1 N2 175.00(5) . . ?
O1 Cu1 N2 83.43(5) . . ?
N1 Cu1 N2 83.38(5) . . ?
O3 Cu1 O3 83.54(4) . 2_665 ?
O1 Cu1 O3 98.52(4) . 2_665 ?
N1 Cu1 O3 92.06(5) . 2_665 ?
N2 Cu1 O3 92.24(4) . 2_665 ?
C8 O1 Cu1 114.73(10) . . ?
C4 O3 Cu1 128.65(10) . . ?
C4 O3 Cu1 114.25(9) . 2_665 ?
Cu1 O3 Cu1 96.46(4) . 2_665 ?
C5 N1 C1 119.13(14) . . ?
C5 N1 Cu1 114.50(11) . . ?
C1 N1 Cu1 126.36(11) . . ?
C6 N2 C7 113.92(12) . . ?
C6 N2 C9 111.39(12) . 2_665 ?
C7 N2 C9 108.22(12) . 2_665 ?
C6 N2 Cu1 108.85(9) . . ?
C7 N2 Cu1 104.95(9) . . ?
C9 N2 Cu1 109.25(9) 2_665 . ?
N1 C1 C12 121.99(15) . . ?
N1 C1 H1 119.0 . . ?
C12 C1 H1 119.0 . . ?
C3 C2 C5 118.99(15) . . ?
C3 C2 H2 120.5 . . ?
C5 C2 H2 120.5 . . ?
C2 C3 C12 119.02(15) . . ?
C2 C3 H3 120.5 . . ?
C12 C3 H3 120.5 . . ?
O3 C4 C14 123.18(14) . . ?
O3 C4 C10 118.53(14) . . ?
C14 C4 C10 118.24(14) . . ?
N1 C5 C2 121.84(15) . . ?
N1 C5 C6 116.13(14) . . ?
C2 C5 C6 121.89(14) . . ?
N2 C6 C5 111.02(12) . . ?
N2 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N2 C7 C8 109.91(12) . . ?
N2 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
N2 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
O2 C8 O1 124.88(15) . . ?
O2 C8 C7 118.79(15) . . ?
O1 C8 C7 116.29(14) . . ?
N2 C9 C10 116.35(13) 2_665 . ?
N2 C9 H9A 108.2 2_665 . ?
C10 C9 H9A 108.2 . . ?
N2 C9 H9B 108.2 2_665 . ?
C10 C9 H9B 108.2 . . ?
H9A C9 H9B 107.4 . . ?
C11 C10 C4 119.68(15) . . ?
C11 C10 C9 120.33(14) . . ?
C4 C10 C9 119.58(14) . . ?
C15 C11 C10 121.67(15) . . ?
C15 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C1 C12 C3 118.95(16) . . ?
C1 C12 H12 120.5 . . ?
C3 C12 H12 120.5 . . ?
C14 C13 C15 121.14(16) . . ?
C14 C13 H13 119.4 . . ?
C15 C13 H13 119.4 . . ?
C13 C14 C4 120.74(15) . . ?
C13 C14 H14 119.6 . . ?
C4 C14 H14 119.6 . . ?
C11 C15 C13 118.41(15) . . ?
C11 C15 H15 120.8 . . ?
C13 C15 H15 120.8 . . ?
C16 O4 H4 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O2 0.95 2.51 3.284(2) 139.0 1_565 yes
C7 H7B O2 0.99 2.63 3.372(2) 132.0 2_666 yes
O4 H4 O2 0.84 1.83 2.6548(18) 167.1 2_666 yes

_refine_diff_density_max         0.695
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-1

