# 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 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_sp1
_database_code_depnum_ccdc_archive 'CCDC 1995185'
loop_
_audit_author_name
_audit_author_address
'Sandip Saha'
;APC College
India
;
_audit_update_record             
;
2020-11-28 deposited with the CCDC.	2021-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 Cu N6 O'
_chemical_formula_sum            'C12 H18 Cu N6 O'
_chemical_formula_weight         325.86

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      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                   9.971(3)
_cell_length_b                   6.885(2)
_cell_length_c                   21.068(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.329(5)
_cell_angle_gamma                90
_cell_volume                     1413.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    442
_cell_measurement_theta_min      6.30
_cell_measurement_theta_max      19.78

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.551
_shelx_estimated_absorpt_T_min   0.860
_shelx_estimated_absorpt_T_max   0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13601
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.979
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2560
_reflns_number_gt                1452
_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       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 1998)'
_computing_data_reduction        SAINT-Plus
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 2012) and SCHAKAL (Keller, 1999)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_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)+(0.0834P)²] 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         2560
_refine_ls_number_parameters     190
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.1648
_refine_ls_wR_factor_gt          0.1464
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.018
_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 0.32115(7) 0.26150(11) 0.43247(4) 0.0478(3) Uani 1 1 d . . . . .
O1 O 0.3436(4) 0.3099(6) 0.5236(2) 0.0550(12) Uani 1 1 d . . . . .
N1 N 0.5215(5) 0.2944(8) 0.4432(3) 0.0454(13) Uani 1 1 d . . . . .
H1AN H 0.535(6) 0.417(9) 0.444(3) 0.055 Uiso 1 1 d . U . . .
H1BN H 0.557(6) 0.245(8) 0.483(3) 0.055 Uiso 1 1 d . U . . .
N2 N 0.2861(6) 0.2627(8) 0.3341(3) 0.0570(14) Uani 1 1 d . . . . .
H2N H 0.283(7) 0.385(10) 0.330(3) 0.068 Uiso 1 1 d . U . . .
N3 N 0.1215(5) 0.2710(8) 0.4192(3) 0.0600(14) Uani 1 1 d . . . . .
N4 N 0.3265(6) -0.0837(8) 0.4374(3) 0.0562(14) Uani 1 1 d . . . . .
N5 N 0.3185(5) -0.2033(7) 0.3972(3) 0.0488(13) Uani 1 1 d . . . . .
N6 N 0.3127(8) -0.3138(9) 0.3569(3) 0.086(2) Uani 1 1 d . . . . .
C1 C 0.5896(7) 0.1994(10) 0.3975(3) 0.064(2) Uani 1 1 d . . . . .
H1A H 0.586408 0.060031 0.403758 0.077 Uiso 1 1 calc R U . . .
H1B H 0.685316 0.238183 0.406755 0.077 Uiso 1 1 calc R U . . .
C2 C 0.5270(8) 0.2457(11) 0.3278(3) 0.0686(19) Uani 1 1 d . . . . .
H2A H 0.525524 0.385657 0.322563 0.082 Uiso 1 1 calc R U . . .
H2B H 0.585970 0.193132 0.300897 0.082 Uiso 1 1 calc R U . . .
C3 C 0.3851(8) 0.1704(11) 0.3032(3) 0.066(2) Uani 1 1 d . . . . .
H3A H 0.359055 0.191713 0.256692 0.079 Uiso 1 1 calc R U . . .
H3B H 0.384055 0.031473 0.310834 0.079 Uiso 1 1 calc R U . . .
C4 C 0.1448(7) 0.1907(9) 0.3107(3) 0.063(2) Uani 1 1 d . . . . .
H4A H 0.142616 0.050641 0.315540 0.076 Uiso 1 1 calc R U . . .
H4B H 0.113194 0.221971 0.265111 0.076 Uiso 1 1 calc R U . . .
C5 C 0.0536(7) 0.2840(11) 0.3496(4) 0.082(3) Uani 1 1 d . . . . .
H5A H 0.037992 0.418936 0.336949 0.098 Uiso 1 1 calc R U . . .
H5B H -0.034356 0.218119 0.341934 0.098 Uiso 1 1 calc R U . . .
C6 C 0.0561(7) 0.2601(10) 0.4635(5) 0.071(2) Uani 1 1 d . . . . .
H6 H -0.039030 0.253882 0.450462 0.085 Uiso 1 1 calc R U . . .
C7 C 0.1110(6) 0.2560(10) 0.5315(4) 0.0610(18) Uani 1 1 d . . . . .
C8 C 0.0221(9) 0.2271(11) 0.5733(5) 0.087(3) Uani 1 1 d . U . . .
H8 H -0.071043 0.210734 0.555853 0.105 Uiso 1 1 calc R U . . .
C9 C 0.0670(10) 0.2222(12) 0.6382(6) 0.100(3) Uani 1 1 d . U . . .
H9 H 0.005149 0.201047 0.664847 0.120 Uiso 1 1 calc R U . . .
C10 C 0.2027(9) 0.2482(11) 0.6649(4) 0.083(2) Uani 1 1 d . U . . .
H10 H 0.232727 0.246609 0.709856 0.100 Uiso 1 1 calc R U . . .
C11 C 0.2958(8) 0.2766(9) 0.6262(4) 0.0646(19) Uani 1 1 d . . . . .
H11 H 0.388417 0.291915 0.644939 0.078 Uiso 1 1 calc R U . . .
C12 C 0.2513(7) 0.2826(8) 0.5587(3) 0.0533(17) Uani 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 O1 1.914(4) . ?
Cu1 N3 1.952(5) . ?
Cu1 N1 1.975(5) . ?
Cu1 N2 2.028(6) . ?
Cu1 N4 2.379(5) . ?
O1 C12 1.312(7) . ?
N1 C1 1.447(8) . ?
N1 H1AN 0.86(6) . ?
N1 H1BN 0.91(6) . ?
N2 C3 1.440(9) . ?
N2 C4 1.475(8) . ?
N2 H2N 0.84(6) . ?
N3 C6 1.249(9) . ?
N3 C5 1.481(9) . ?
N4 N5 1.171(7) . ?
N5 N6 1.133(7) . ?
C1 C2 1.502(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.492(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.493(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.421(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(10) . ?
C7 C12 1.406(9) . ?
C8 C9 1.345(13) . ?
C8 H8 0.9300 . ?
C9 C10 1.362(12) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.396(9) . ?
C11 H11 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
O1 Cu1 N3 92.0(2) . . ?
O1 Cu1 N1 88.09(19) . . ?
N3 Cu1 N1 171.3(2) . . ?
O1 Cu1 N2 169.3(2) . . ?
N3 Cu1 N2 84.6(2) . . ?
N1 Cu1 N2 93.8(2) . . ?
O1 Cu1 N4 97.64(19) . . ?
N3 Cu1 N4 93.0(2) . . ?
N1 Cu1 N4 95.6(2) . . ?
N2 Cu1 N4 92.7(2) . . ?
C12 O1 Cu1 126.5(4) . . ?
C1 N1 Cu1 118.6(4) . . ?
C1 N1 H1AN 112(4) . . ?
Cu1 N1 H1AN 106(4) . . ?
C1 N1 H1BN 108(4) . . ?
Cu1 N1 H1BN 104(4) . . ?
H1AN N1 H1BN 108(5) . . ?
C3 N2 C4 113.5(6) . . ?
C3 N2 Cu1 118.3(4) . . ?
C4 N2 Cu1 106.4(4) . . ?
C3 N2 H2N 114(5) . . ?
C4 N2 H2N 106(5) . . ?
Cu1 N2 H2N 96(5) . . ?
C6 N3 C5 122.8(6) . . ?
C6 N3 Cu1 124.8(5) . . ?
C5 N3 Cu1 112.3(5) . . ?
N5 N4 Cu1 132.3(4) . . ?
N6 N5 N4 177.3(7) . . ?
N1 C1 C2 113.5(6) . . ?
N1 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 115.6(6) . . ?
C3 C2 H2A 108.4 . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C1 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
N2 C3 C2 112.3(6) . . ?
N2 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
N2 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
N2 C4 C5 108.8(5) . . ?
N2 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
N2 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N3 C5 C4 108.3(5) . . ?
N3 C5 H5A 110.0 . . ?
C4 C5 H5A 110.0 . . ?
N3 C5 H5B 110.0 . . ?
C4 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
N3 C6 C7 127.1(6) . . ?
N3 C6 H6 116.4 . . ?
C7 C6 H6 116.4 . . ?
C8 C7 C12 118.3(8) . . ?
C8 C7 C6 118.7(7) . . ?
C12 C7 C6 123.0(6) . . ?
C9 C8 C7 121.9(8) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C10 120.2(8) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 120.7(8) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 120.1(8) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
O1 C12 C11 118.0(6) . . ?
O1 C12 C7 123.0(6) . . ?
C11 C12 C7 118.9(6) . . ?

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
N1 H1AN O1 0.85(6) 2.26(6) 3.053(7) 154(6) 3_666
N1 H1BN N4 0.90(6) 2.14(6) 3.017(8) 164(5) 3_656
N2 H2N N6 0.85(7) 2.15(7) 2.958(8) 158(6) 1_565
C3 H3A N6 0.97 2.63 3.527(9) 154 2_555

_refine_diff_density_max         0.879
_refine_diff_density_min         -0.847
_refine_diff_density_rms         0.103



