# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_sd54_sq
_database_code_depnum_ccdc_archive 'CCDC 2260302'
loop_
_audit_author_name
_audit_author_address
'Nattamai S. P. Bhuvanesh'
;Department of Chemistry, Texas A and M University, College Station, USA
United States of America
;
_audit_update_record             
;
2023-05-03 deposited with the CCDC.	2023-08-17 downloaded from the CCDC.
;
_audit_creation_date             2016-01-06
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.5(C36 H40 Cu4 N4 O16 Se4)'
_chemical_formula_sum            'C18 H20 Cu2 N2 O8 Se2'
_chemical_formula_weight         677.36
_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'
Cu Cu -1.9646 0.5888 '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'
Se Se -0.7943 1.1372 '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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   12.7110(4)
_cell_length_b                   25.3176(8)
_cell_length_c                   8.7136(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2804.14(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    99.99
_cell_measurement_theta_max      70.055
_cell_measurement_theta_min      3.491
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.568
_exptl_absorpt_coefficient_mu    5.185
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0976 before and 0.0643 after correction.
The Ratio of minimum to maximum transmission is 0.8018.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.012
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            49402
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.204
_diffrn_reflns_theta_min         3.491
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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                2343
_reflns_number_total             2651
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2651
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0235
_refine_ls_restrained_S_all      1.067
_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)+(0.0347P)²+1.9487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0613
_refine_ls_wR_factor_ref         0.0632
_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:
 C5(H5), C6(H6), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Se1 Se 0.34046(2) 0.25280(2) 1.05275(3) 0.01983(9) Uani 1 1 d . . . . .
Cu1 Cu 0.46671(2) 0.45768(2) 0.57117(3) 0.01474(10) Uani 1 1 d . . . . .
O1 O 0.43619(16) 0.42913(7) 0.36614(19) 0.0307(4) Uani 1 1 d . . . . .
O2 O 0.49443(14) 0.50103(7) 0.24675(17) 0.0255(4) Uani 1 1 d . . . . .
O3 O 0.67187(12) 0.50746(7) 0.4307(2) 0.0284(4) Uani 1 1 d . . . . .
O4 O 0.61461(13) 0.43531(7) 0.5496(2) 0.0302(4) Uani 1 1 d . . . . .
N1 N 0.42290(15) 0.38936(7) 0.7071(2) 0.0182(4) Uani 1 1 d . . . . .
C1 C 0.45522(17) 0.45586(9) 0.2474(3) 0.0186(5) Uani 1 1 d . . . . .
C2 C 0.4264(2) 0.43243(11) 0.0946(3) 0.0274(5) Uani 1 1 d . . . . .
H2A H 0.4317 0.3939 0.1000 0.041 Uiso 1 1 calc GR . . . .
H2B H 0.4745 0.4457 0.0157 0.041 Uiso 1 1 calc GR . . . .
H2C H 0.3541 0.4424 0.0684 0.041 Uiso 1 1 calc GR . . . .
C3 C 0.68568(18) 0.46276(9) 0.4890(3) 0.0209(5) Uani 1 1 d . . . . .
C4 C 0.7957(2) 0.44091(12) 0.4897(4) 0.0347(6) Uani 1 1 d . . . . .
H4A H 0.8278 0.4461 0.3886 0.052 Uiso 1 1 calc GR . . . .
H4B H 0.7934 0.4031 0.5135 0.052 Uiso 1 1 calc GR . . . .
H4C H 0.8375 0.4593 0.5677 0.052 Uiso 1 1 calc GR . . . .
C5 C 0.49470(18) 0.35473(9) 0.7597(3) 0.0203(5) Uani 1 1 d . . . . .
H5 H 0.5656 0.3587 0.7273 0.024 Uiso 1 1 calc R . . . .
C6 C 0.47072(18) 0.31390(9) 0.8581(3) 0.0196(5) Uani 1 1 d . . . . .
H6 H 0.5237 0.2902 0.8924 0.023 Uiso 1 1 calc R . . . .
C7 C 0.36634(18) 0.30811(8) 0.9061(2) 0.0168(4) Uani 1 1 d . . . . .
C8 C 0.29126(18) 0.34310(9) 0.8538(3) 0.0181(4) Uani 1 1 d . . . . .
H8 H 0.2197 0.3400 0.8841 0.022 Uiso 1 1 calc R . . . .
C9 C 0.32361(18) 0.38289(9) 0.7557(3) 0.0204(5) Uani 1 1 d . . . . .
H9 H 0.2721 0.4072 0.7205 0.024 Uiso 1 1 calc R . . . .


_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
Se1 Se1 2.3040(5) 2 ?
Se1 C7 1.924(2) . ?
Cu1 Cu1 2.6166(6) 5_666 ?
Cu1 O1 1.9658(17) . ?
Cu1 O2 1.9632(16) 5_666 ?
Cu1 O3 1.9702(17) 5_666 ?
Cu1 O4 1.9723(17) . ?
Cu1 N1 2.1692(19) . ?
O1 C1 1.259(3) . ?
O2 Cu1 1.9632(16) 5_666 ?
O2 C1 1.248(3) . ?
O3 Cu1 1.9703(17) 5_666 ?
O3 C3 1.253(3) . ?
O4 C3 1.256(3) . ?
N1 C5 1.346(3) . ?
N1 C9 1.341(3) . ?
C1 C2 1.503(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.504(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C6 1.377(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.399(3) . ?
C7 C8 1.380(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(3) . ?
C9 H9 0.9500 . ?

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 Se1 Se1 102.44(7) . 2 ?
O1 Cu1 Cu1 86.23(5) . 5_666 ?
O1 Cu1 O3 88.89(8) . 5_666 ?
O1 Cu1 O4 89.77(8) . . ?
O1 Cu1 N1 98.78(7) . . ?
O2 Cu1 Cu1 82.27(5) 5_666 5_666 ?
O2 Cu1 O1 168.49(7) 5_666 . ?
O2 Cu1 O3 89.61(8) 5_666 5_666 ?
O2 Cu1 O4 89.43(8) 5_666 . ?
O2 Cu1 N1 92.73(7) 5_666 . ?
O3 Cu1 Cu1 85.32(5) 5_666 5_666 ?
O3 Cu1 O4 168.51(7) 5_666 . ?
O3 Cu1 N1 97.60(7) 5_666 . ?
O4 Cu1 Cu1 83.20(5) . 5_666 ?
O4 Cu1 N1 93.89(7) . . ?
N1 Cu1 Cu1 174.23(5) . 5_666 ?
C1 O1 Cu1 120.72(15) . . ?
C1 O2 Cu1 125.78(15) . 5_666 ?
C3 O3 Cu1 122.23(15) . 5_666 ?
C3 O4 Cu1 124.52(16) . . ?
C5 N1 Cu1 122.09(15) . . ?
C9 N1 Cu1 120.76(15) . . ?
C9 N1 C5 116.8(2) . . ?
O1 C1 C2 118.0(2) . . ?
O2 C1 O1 125.0(2) . . ?
O2 C1 C2 117.1(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O3 C3 O4 124.7(2) . . ?
O3 C3 C4 117.7(2) . . ?
O4 C3 C4 117.6(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5 118.3 . . ?
N1 C5 C6 123.4(2) . . ?
C6 C5 H5 118.3 . . ?
C5 C6 H6 120.8 . . ?
C5 C6 C7 118.4(2) . . ?
C7 C6 H6 120.8 . . ?
C6 C7 Se1 115.93(17) . . ?
C8 C7 Se1 124.66(17) . . ?
C8 C7 C6 119.3(2) . . ?
C7 C8 H8 121.1 . . ?
C7 C8 C9 117.8(2) . . ?
C9 C8 H8 121.1 . . ?
N1 C9 C8 124.3(2) . . ?
N1 C9 H9 117.8 . . ?
C8 C9 H9 117.8 . . ?

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
Se1 C7 C8 C9 175.90(17) . . . . ?
Cu1 O1 C1 O2 0.6(3) . . . . ?
Cu1 O1 C1 C2 -177.84(16) . . . . ?
Cu1 O2 C1 O1 -1.4(3) 5_666 . . . ?
Cu1 O2 C1 C2 177.01(16) 5_666 . . . ?
Cu1 O3 C3 O4 0.9(4) 5_666 . . . ?
Cu1 O3 C3 C4 -177.53(18) 5_666 . . . ?
Cu1 O4 C3 O3 -1.8(4) . . . . ?
Cu1 O4 C3 C4 176.68(18) . . . . ?
Cu1 N1 C5 C6 173.66(17) . . . . ?
Cu1 N1 C9 C8 -174.03(18) . . . . ?
N1 C5 C6 C7 -0.1(3) . . . . ?
C5 N1 C9 C8 -0.6(3) . . . . ?
C5 C6 C7 Se1 -176.46(17) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C7 C8 C9 N1 0.7(4) . . . . ?
C9 N1 C5 C6 0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
