# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_23febd_0m
_database_code_depnum_ccdc_archive 'CCDC 2162215'
loop_
_audit_author_name
_audit_author_address
'Rakesh Kumar'
;Indian Institute of Technology Kanpur India
India
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;
_audit_creation_date             2023-03-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H20 Cu N4 O2, H2 O'
_chemical_formula_sum            'C12 H22 Cu N4 O3'
_chemical_formula_weight         333.87
_chemical_absolute_configuration none
_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 0.0033 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'

_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      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'y, x, -z'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'

_cell_length_a                   8.5368(4)
_cell_length_b                   8.5368(4)
_cell_length_c                   17.4591(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1101.90(12)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   0.795
_shelx_estimated_absorpt_T_min   0.754
_exptl_absorpt_coefficient_mu    1.499
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4970
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1893 before and 0.0782 after correction.
The Ratio of minimum to maximum transmission is 0.6665.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             525
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13297
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         2.755
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1266
_reflns_number_total             1291
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.019(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0202
_refine_ls_R_factor_gt           0.0196
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0228P)²+0.3078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0503
_refine_ls_wR_factor_ref         0.0510
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.981(19)
 0.019(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
3. Others
 Fixed Sof: H2C(0.5) H2D(0.5)
4.a Free rotating group:
 O2(H2C,H2D)
4.b Ternary CH refined with riding coordinates:
 N1(H1), C4(H4)
4.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C2(H2A,H2B), C3(H3A,H3B), C1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Cu1 Cu 0.000000 0.62358(4) 0.333333 0.00979(14) Uani 1 2 d S T P . .
O2 O 0.3366(3) 0.3366(3) 0.500000 0.0219(6) Uani 1 2 d GS T P . .
H2C H 0.235270 0.329506 0.512744 0.033 Uiso 0.5 1 d G U P . .
H2D H 0.311563 0.223351 0.499068 0.033 Uiso 0.5 1 d G U P . .
O1 O 0.2898(3) 0.9878(2) 0.49293(10) 0.0199(4) Uani 1 1 d . . . . .
N1 N 0.1573(3) 0.5593(3) 0.39465(11) 0.0110(5) Uani 1 1 d . . . . .
H1 H 0.079692 0.447774 0.425265 0.013 Uiso 1 1 calc R U . . .
N2 N 0.1172(3) 0.8466(3) 0.38679(11) 0.0146(4) Uani 1 1 d . . . . .
C5 C 0.2244(3) 0.8638(3) 0.44401(14) 0.0120(5) Uani 1 1 d . . . . .
C4 C 0.2725(4) 0.7135(4) 0.44825(14) 0.0120(5) Uani 1 1 d . . . . .
H4 H 0.254250 0.666515 0.501905 0.014 Uiso 1 1 calc R U . . .
C6 C 0.0420(4) 0.9648(4) 0.37375(15) 0.0169(6) Uani 1 1 d . . . . .
H6A H 0.138437 1.093196 0.377239 0.020 Uiso 1 1 calc R U . . .
H6B H -0.051427 0.941987 0.412643 0.020 Uiso 1 1 calc R U . . .
C2 C 0.4526(4) 0.7142(4) 0.34127(17) 0.0236(6) Uani 1 1 d . . . . .
H2A H 0.436616 0.794615 0.305220 0.028 Uiso 1 1 calc R U . . .
H2B H 0.559677 0.705631 0.325795 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4691(4) 0.7799(4) 0.42408(16) 0.0218(6) Uani 1 1 d . . . . .
H3A H 0.542691 0.913372 0.426915 0.026 Uiso 1 1 calc R U . . .
H3B H 0.524861 0.726662 0.457033 0.026 Uiso 1 1 calc R U . . .
C1 C 0.2837(4) 0.5285(4) 0.34549(14) 0.0160(6) Uani 1 1 d . . . . .
H1A H 0.231780 0.485259 0.293899 0.019 Uiso 1 1 calc R U . . .
H1B H 0.310491 0.439162 0.369196 0.019 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 N1 1.997(2) . ?
Cu1 N1 1.997(2) 6 ?
Cu1 N2 1.895(2) . ?
Cu1 N2 1.8954(19) 6 ?
O2 H2C 0.8654 . ?
O2 H2C 0.87(12) 4_556 ?
O2 H2D 0.88(14) 4_556 ?
O2 H2D 0.8796 . ?
O1 C5 1.253(3) . ?
N1 H1 1.0000 . ?
N1 C4 1.510(3) . ?
N1 C1 1.501(3) . ?
N2 C5 1.313(3) . ?
N2 C6 1.459(3) . ?
C5 C4 1.533(4) . ?
C4 H4 1.0000 . ?
C4 C3 1.538(4) . ?
C6 C6 1.542(5) 6 ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.531(4) . ?
C2 C1 1.521(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?

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 Cu1 N1 104.66(12) 6 . ?
N2 Cu1 N1 85.56(9) . . ?
N2 Cu1 N1 85.56(9) 6 6 ?
N2 Cu1 N1 169.35(9) 6 . ?
N2 Cu1 N1 169.35(9) . 6 ?
N2 Cu1 N2 84.41(13) 6 . ?
H2C O2 H2C 115.4 . 4_556 ?
H2C O2 H2D 104.1 4_556 4_556 ?
H2C O2 H2D 104.1 . . ?
H2C O2 H2D 16.2 . 4_556 ?
H2D O2 H2C 16.2 . 4_556 ?
H2D O2 H2D 95.7 . 4_556 ?
Cu1 N1 H1 109.4 . . ?
C4 N1 Cu1 109.07(15) . . ?
C4 N1 H1 109.4 . . ?
C1 N1 Cu1 112.48(15) . . ?
C1 N1 H1 109.4 . . ?
C1 N1 C4 107.17(19) . . ?
C5 N2 Cu1 118.38(18) . . ?
C5 N2 C6 124.4(2) . . ?
C6 N2 Cu1 115.11(16) . . ?
O1 C5 N2 127.2(2) . . ?
O1 C5 C4 118.8(2) . . ?
N2 C5 C4 114.0(2) . . ?
N1 C4 C5 111.7(2) . . ?
N1 C4 H4 109.1 . . ?
N1 C4 C3 105.4(2) . . ?
C5 C4 H4 109.1 . . ?
C5 C4 C3 112.2(2) . . ?
C3 C4 H4 109.1 . . ?
N2 C6 C6 107.23(15) . 6 ?
N2 C6 H6A 110.3 . . ?
N2 C6 H6B 110.3 . . ?
C6 C6 H6A 110.3 6 . ?
C6 C6 H6B 110.3 6 . ?
H6A C6 H6B 108.5 . . ?
H2A C2 H2B 109.3 . . ?
C3 C2 H2A 111.4 . . ?
C3 C2 H2B 111.4 . . ?
C1 C2 H2A 111.4 . . ?
C1 C2 H2B 111.4 . . ?
C1 C2 C3 101.6(2) . . ?
C4 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C2 C3 C4 103.9(2) . . ?
C2 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
N1 C1 C2 103.6(2) . . ?
N1 C1 H1A 111.0 . . ?
N1 C1 H1B 111.0 . . ?
C2 C1 H1A 111.0 . . ?
C2 C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?

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
Cu1 N1 C4 C5 4.4(2) . . . . ?
Cu1 N1 C4 C3 -117.78(18) . . . . ?
Cu1 N1 C1 C2 91.0(2) . . . . ?
Cu1 N2 C5 O1 -167.9(2) . . . . ?
Cu1 N2 C5 C4 13.0(3) . . . . ?
Cu1 N2 C6 C6 -28.4(3) . . . 6 ?
O1 C5 C4 N1 169.8(2) . . . . ?
O1 C5 C4 C3 -72.1(3) . . . . ?
N1 Cu1 N2 C5 155.4(4) 6 . . . ?
N1 Cu1 N2 C5 -8.47(19) . . . . ?
N1 Cu1 N2 C6 -172.6(2) . . . . ?
N1 Cu1 N2 C6 -8.7(6) 6 . . . ?
N1 C4 C3 C2 21.8(3) . . . . ?
N2 Cu1 N2 C5 175.1(3) 6 . . . ?
N2 Cu1 N2 C6 11.01(14) 6 . . . ?
N2 C5 C4 N1 -11.0(3) . . . . ?
N2 C5 C4 C3 107.2(3) . . . . ?
C5 N2 C6 C6 168.5(3) . . . 6 ?
C5 C4 C3 C2 -100.0(2) . . . . ?
C4 N1 C1 C2 -28.9(3) . . . . ?
C6 N2 C5 O1 -5.3(4) . . . . ?
C6 N2 C5 C4 175.5(2) . . . . ?
C3 C2 C1 N1 41.9(3) . . . . ?
C1 N1 C4 C5 126.4(2) . . . . ?
C1 N1 C4 C3 4.2(3) . . . . ?
C1 C2 C3 C4 -39.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.981(19)
2 0.019(19)

