# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_BS_RR
_database_code_depnum_ccdc_archive 'CCDC 2183901'
loop_
_audit_author_name
_audit_author_address
'Bipul Sarma'
;Tezpur University
India
;
_audit_update_record             
;
2022-07-04 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H28 Cu2 N4 O10'
_chemical_formula_weight         539.48

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.240(7)
_cell_length_b                   8.487(5)
_cell_length_c                   13.274(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.29(4)
_cell_angle_gamma                90
_cell_volume                     1101.5(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1564
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      20.37

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.987
_shelx_estimated_absorpt_T_min   0.560
_shelx_estimated_absorpt_T_max   0.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.542
_exptl_absorpt_correction_T_max  0.697
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23181
_diffrn_reflns_av_unetI/netI     0.1159
_diffrn_reflns_av_R_equivalents  0.1399
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.888
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measured_fraction_theta_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.927
_reflns_number_total             2038
_reflns_number_gt                1240
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2038
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   0.852
_refine_ls_restrained_S_all      0.852
_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_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 0.91643(5) 0.08049(5) 0.04082(4) 0.02976(18) Uani 1 1 d . . . . .
C5 C 1.1585(5) 0.4075(4) -0.0661(4) 0.0571(15) Uani 1 1 d . . . . .
H5A H 1.1073 0.4956 -0.0526 0.086 Uiso 1 1 calc R U . . .
H5B H 1.1569 0.4085 -0.1388 0.086 Uiso 1 1 calc R U . . .
H5C H 1.2514 0.4147 -0.0218 0.086 Uiso 1 1 calc R U . . .
C4 C 1.0958(5) 0.2569(4) -0.0427(3) 0.0311(10) Uani 1 1 d . . . . .
O2 O 0.7893(3) 0.0705(3) -0.1021(2) 0.0436(8) Uani 1 1 d . . . . .
O5 O 1.0723(3) 0.0658(3) 0.1707(2) 0.0436(8) Uani 1 1 d . . . . .
O3 O 1.0038(3) 0.2655(3) 0.0017(2) 0.0415(8) Uani 1 1 d . . . . .
O4 O 0.8578(3) -0.1313(3) 0.0690(2) 0.0426(8) Uani 1 1 d . . . . .
O1 O 0.7806(3) 0.1958(3) 0.1118(2) 0.0408(8) Uani 1 1 d . . . . .
C6 C 0.8151(5) 0.0012(5) -0.1761(4) 0.0367(11) Uani 1 1 d . . . . .
N1 N 0.6913(4) 0.3419(5) 0.2177(4) 0.0448(11) Uani 1 1 d . . . . .
C1 C 0.7983(5) 0.2652(5) 0.1988(4) 0.0349(11) Uani 1 1 d . . . . .
N2 N 0.9190(4) 0.2717(4) 0.2726(3) 0.0446(11) Uani 1 1 d . . . . .
C3 C 0.5578(5) 0.3446(6) 0.1427(4) 0.0594(14) Uani 1 1 d . . . . .
H3A H 0.5638 0.3858 0.0768 0.089 Uiso 1 1 calc R U . . .
H3B H 0.4987 0.4103 0.1687 0.089 Uiso 1 1 calc R U . . .
H3C H 0.5216 0.2395 0.1323 0.089 Uiso 1 1 calc R U . . .
C2 C 0.9510(5) 0.3574(6) 0.3716(4) 0.0598(14) Uani 1 1 d . . . . .
H2A H 0.9220 0.4649 0.3581 0.090 Uiso 1 1 calc R U . . .
H2B H 1.0479 0.3542 0.4054 0.090 Uiso 1 1 calc R U . . .
H2C H 0.9044 0.3096 0.4167 0.090 Uiso 1 1 calc R U . . .
C7 C 0.7073(5) -0.0066(6) -0.2805(4) 0.0721(17) Uani 1 1 d . . . . .
H7A H 0.6221 -0.0383 -0.2703 0.108 Uiso 1 1 calc R U . . .
H7B H 0.7336 -0.0818 -0.3249 0.108 Uiso 1 1 calc R U . . .
H7C H 0.6968 0.0952 -0.3134 0.108 Uiso 1 1 calc R U . . .
H1 H 0.702(4) 0.369(4) 0.276(3) 0.021(12) Uiso 1 1 d . . . . .
H2 H 0.983(4) 0.213(4) 0.259(3) 0.044(13) 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 O3 1.952(3) . ?
Cu1 O2 1.958(3) . ?
Cu1 O4 1.966(3) . ?
Cu1 O5 1.975(3) . ?
Cu1 O1 2.135(3) . ?
Cu1 Cu1 2.6595(15) 3_755 ?
C5 C4 1.503(5) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C4 O3 1.254(5) . ?
C4 O4 1.258(4) 3_755 ?
O2 C6 1.239(5) . ?
O5 C6 1.268(5) 3_755 ?
O4 C4 1.258(4) 3_755 ?
O1 C1 1.261(5) . ?
C6 O5 1.268(5) 3_755 ?
C6 C7 1.495(6) . ?
N1 C1 1.361(5) . ?
N1 C3 1.432(6) . ?
N1 H1 0.79(4) . ?
C1 N2 1.330(6) . ?
N2 C2 1.451(6) . ?
N2 H2 0.88(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

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 O2 90.13(13) . . ?
O3 Cu1 O4 167.43(11) . . ?
O2 Cu1 O4 89.55(12) . . ?
O3 Cu1 O5 88.14(13) . . ?
O2 Cu1 O5 167.25(11) . . ?
O4 Cu1 O5 89.40(13) . . ?
O3 Cu1 O1 99.14(11) . . ?
O2 Cu1 O1 96.57(13) . . ?
O4 Cu1 O1 93.38(11) . . ?
O5 Cu1 O1 96.18(13) . . ?
O3 Cu1 Cu1 84.47(9) . 3_755 ?
O2 Cu1 Cu1 84.62(10) . 3_755 ?
O4 Cu1 Cu1 82.99(9) . 3_755 ?
O5 Cu1 Cu1 82.64(9) . 3_755 ?
O1 Cu1 Cu1 176.18(8) . 3_755 ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C4 O4 125.3(4) . 3_755 ?
O3 C4 C5 118.3(4) . . ?
O4 C4 C5 116.4(4) 3_755 . ?
C6 O2 Cu1 123.5(3) . . ?
C6 O5 Cu1 124.3(3) 3_755 . ?
C4 O3 Cu1 123.1(2) . . ?
C4 O4 Cu1 124.1(3) 3_755 . ?
C1 O1 Cu1 133.1(3) . . ?
O2 C6 O5 124.9(4) . 3_755 ?
O2 C6 C7 118.9(4) . . ?
O5 C6 C7 116.2(4) 3_755 . ?
C1 N1 C3 122.3(4) . . ?
C1 N1 H1 116(3) . . ?
C3 N1 H1 120(3) . . ?
O1 C1 N2 122.9(4) . . ?
O1 C1 N1 119.2(4) . . ?
N2 C1 N1 117.9(4) . . ?
C1 N2 C2 126.7(4) . . ?
C1 N2 H2 114(3) . . ?
C2 N2 H2 119(3) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.086

