# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_complex1
_database_code_depnum_ccdc_archive 'CCDC 2240116'
loop_
_audit_author_name
_audit_author_address
'Bidraha Bagh'
;National Institute of Science Education and Research (NISER), Bhubaneswar
India
;
_audit_update_record             
;
2023-02-06 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_audit_creation_date             2023-02-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 Cu I N3 O'
_chemical_formula_sum            'C16 H15 Cu I N3 O'
_chemical_formula_weight         455.75
_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'
I I -0.4742 1.8119 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.2982(5)
_cell_length_b                   8.7867(3)
_cell_length_c                   15.5899(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.228(4)
_cell_angle_gamma                90
_cell_volume                     1590.68(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9522
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.6530
_cell_measurement_theta_min      3.5880
_shelx_estimated_absorpt_T_max   0.733
_shelx_estimated_absorpt_T_min   0.557
_exptl_absorpt_coefficient_mu    3.318
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.903
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.788
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15069
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.788
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.439
_diffrn_reflns_theta_min         3.460
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.788
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  19.00   0.50    3.08    --    3.51-101.00 135.00   68
  2  ω     -4.00  29.00   0.50    3.08    --   -4.14-101.00 135.00   66
  3  ω     -9.00  26.00   0.50    3.08    --    3.51 -99.00   0.00   70
  4  ω     18.00  70.00   0.50    3.08    --    3.51  37.00  60.00  104
  5  ω     -4.00  25.00   0.50    3.08    --   -4.14 -99.00 150.00   58
  6  ω    -24.00  19.00   0.50    3.08    --   -4.14 -77.00 -30.00   86
  7  ω    -27.00  13.00   0.50    3.08    --   -4.14  77.00-180.00   80
  8  ω    -27.00  21.00   0.50    3.08    --   -4.14  77.00 150.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3347
_reflns_number_total             3809
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3809
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.038
_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)+(0.0267P)²+0.9317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0644
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C1(H1), C8(H8), C7(H7), C4(H4), C3(H3), C13(H13),
 C14(H14), C2(H2)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_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
I1 I 0.47049(2) 0.24414(2) 0.48300(2) 0.01381(7) Uani 1 1 d . . . . .
Cu1 Cu 0.50887(2) 0.48852(4) 0.58550(2) 0.01219(8) Uani 1 1 d . . . . .
O1 O 0.94002(18) 0.2376(2) 0.83498(14) 0.0232(5) Uani 1 1 d . . . . .
N3 N 0.64229(17) 0.4858(2) 0.71280(13) 0.0115(4) Uani 1 1 d . . . . .
N2 N 0.60951(18) 0.5465(3) 0.78074(14) 0.0131(4) Uani 1 1 d . . . . .
N1 N 0.37627(17) 0.4847(3) 0.64173(14) 0.0136(4) Uani 1 1 d . . . . .
C11 C 0.7737(2) 0.3597(3) 0.60736(17) 0.0147(5) Uani 1 1 d . . . . .
H11 H 0.710990 0.425639 0.578640 0.018 Uiso 1 1 calc R U . . .
C12 C 0.8268(2) 0.2829(3) 0.55397(19) 0.0189(6) Uani 1 1 d . . . . .
H12 H 0.800042 0.294991 0.489832 0.023 Uiso 1 1 calc R U . . .
C9 C 0.7449(2) 0.4197(3) 0.75470(16) 0.0120(5) Uani 1 1 d . . . . .
C1 C 0.2810(2) 0.3998(3) 0.60797(18) 0.0176(5) Uani 1 1 d . . . . .
H1 H 0.263786 0.359098 0.548517 0.021 Uiso 1 1 calc R U . . .
C6 C 0.5053(2) 0.6387(3) 0.76017(17) 0.0144(5) Uani 1 1 d . . . . .
H6A H 0.505186 0.715618 0.713722 0.017 Uiso 1 1 calc R U . . .
H6B H 0.505375 0.693394 0.815709 0.017 Uiso 1 1 calc R U . . .
C10 C 0.8090(2) 0.3436(3) 0.70145(17) 0.0129(5) Uani 1 1 d . . . . .
C8 C 0.7751(2) 0.4381(3) 0.84943(17) 0.0172(5) Uani 1 1 d . . . . .
H8 H 0.842838 0.402396 0.894581 0.021 Uiso 1 1 calc R U . . .
C5 C 0.3979(2) 0.5430(3) 0.72573(16) 0.0123(5) Uani 1 1 d . . . . .
C7 C 0.6869(2) 0.5180(3) 0.86304(17) 0.0167(5) Uani 1 1 d . . . . .
H7 H 0.681192 0.547855 0.919984 0.020 Uiso 1 1 calc R U . . .
C4 C 0.3282(2) 0.5149(3) 0.77828(18) 0.0180(5) Uani 1 1 d . . . . .
H4 H 0.346841 0.556721 0.837587 0.022 Uiso 1 1 calc R U . . .
C3 C 0.2314(2) 0.4254(3) 0.74303(19) 0.0215(6) Uani 1 1 d . . . . .
H3 H 0.182935 0.403114 0.777898 0.026 Uiso 1 1 calc R U . . .
C13 C 0.9191(2) 0.1887(3) 0.59567(19) 0.0195(6) Uani 1 1 d . . . . .
H13 H 0.955248 0.134378 0.559804 0.023 Uiso 1 1 calc R U . . .
C14 C 0.9594(2) 0.1728(3) 0.68960(19) 0.0191(6) Uani 1 1 d . . . . .
H14 H 1.023966 0.109419 0.717663 0.023 Uiso 1 1 calc R U . . .
C16 C 1.0339(2) 0.1375(4) 0.8782(2) 0.0283(7) Uani 1 1 d . . . . .
H16A H 1.017090 0.035927 0.851122 0.042 Uiso 1 1 calc R U . . .
H16B H 1.044650 0.131412 0.943251 0.042 Uiso 1 1 calc R U . . .
H16C H 1.104396 0.176675 0.869856 0.042 Uiso 1 1 calc R U . . .
C2 C 0.2065(2) 0.3687(3) 0.6558(2) 0.0220(6) Uani 1 1 d . . . . .
H2 H 0.139272 0.309309 0.629084 0.026 Uiso 1 1 calc R U . . .
C15 C 0.9055(2) 0.2495(3) 0.74276(19) 0.0162(5) 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
I1 Cu1 2.6250(4) . ?
I1 Cu1 2.6271(3) 3_666 ?
Cu1 Cu1 2.6101(6) 3_666 ?
Cu1 N3 2.118(2) . ?
Cu1 N1 2.091(2) . ?
O1 C16 1.431(3) . ?
O1 C15 1.362(3) . ?
N3 N2 1.360(3) . ?
N3 C9 1.346(3) . ?
N2 C6 1.460(3) . ?
N2 C7 1.345(3) . ?
N1 C1 1.342(3) . ?
N1 C5 1.349(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(4) . ?
C11 C10 1.393(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(4) . ?
C9 C10 1.480(3) . ?
C9 C8 1.409(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.508(4) . ?
C10 C15 1.415(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.366(4) . ?
C5 C4 1.389(4) . ?
C7 H7 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.381(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.385(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.394(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C2 H2 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
Cu1 I1 Cu1 59.599(11) . 3_666 ?
I1 Cu1 I1 120.401(11) . 3_666 ?
Cu1 Cu1 I1 60.240(12) 3_666 . ?
Cu1 Cu1 I1 60.161(12) 3_666 3_666 ?
N3 Cu1 I1 104.02(6) . 3_666 ?
N3 Cu1 I1 119.32(6) . . ?
N3 Cu1 Cu1 137.42(6) . 3_666 ?
N1 Cu1 I1 103.51(6) . . ?
N1 Cu1 I1 112.20(6) . 3_666 ?
N1 Cu1 Cu1 127.96(6) . 3_666 ?
N1 Cu1 N3 94.44(8) . . ?
C15 O1 C16 117.8(2) . . ?
N2 N3 Cu1 112.85(15) . . ?
C9 N3 Cu1 140.57(17) . . ?
C9 N3 N2 105.18(19) . . ?
N3 N2 C6 120.69(19) . . ?
C7 N2 N3 111.8(2) . . ?
C7 N2 C6 127.3(2) . . ?
C1 N1 Cu1 123.05(17) . . ?
C1 N1 C5 117.3(2) . . ?
C5 N1 Cu1 118.03(16) . . ?
C12 C11 H11 118.8 . . ?
C12 C11 C10 122.4(2) . . ?
C10 C11 H11 118.8 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.0(3) . . ?
C13 C12 H12 120.5 . . ?
N3 C9 C10 120.7(2) . . ?
N3 C9 C8 109.9(2) . . ?
C8 C9 C10 129.4(2) . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 123.0(2) . . ?
C2 C1 H1 118.5 . . ?
N2 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
N2 C6 C5 111.8(2) . . ?
H6A C6 H6B 107.9 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 C15 117.6(2) . . ?
C15 C10 C9 122.1(2) . . ?
C9 C8 H8 127.1 . . ?
C7 C8 C9 105.9(2) . . ?
C7 C8 H8 127.1 . . ?
N1 C5 C6 115.2(2) . . ?
N1 C5 C4 122.9(2) . . ?
C4 C5 C6 121.8(2) . . ?
N2 C7 C8 107.2(2) . . ?
N2 C7 H7 126.4 . . ?
C8 C7 H7 126.4 . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 H4 120.5 . . ?
C4 C3 H3 120.7 . . ?
C4 C3 C2 118.6(2) . . ?
C2 C3 H3 120.7 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.5 . . ?
O1 C15 C10 116.6(2) . . ?
O1 C15 C14 123.1(2) . . ?
C14 C15 C10 120.2(2) . . ?

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 N3 N2 C6 -15.6(3) . . . . ?
Cu1 N3 N2 C7 168.27(17) . . . . ?
Cu1 N3 C9 C10 16.8(4) . . . . ?
Cu1 N3 C9 C8 -163.8(2) . . . . ?
Cu1 N1 C1 C2 164.4(2) . . . . ?
Cu1 N1 C5 C6 14.5(3) . . . . ?
Cu1 N1 C5 C4 -164.16(19) . . . . ?
N3 N2 C6 C5 72.8(3) . . . . ?
N3 N2 C7 C8 1.1(3) . . . . ?
N3 C9 C10 C11 10.2(4) . . . . ?
N3 C9 C10 C15 -168.1(2) . . . . ?
N3 C9 C8 C7 -0.1(3) . . . . ?
N2 N3 C9 C10 -178.7(2) . . . . ?
N2 N3 C9 C8 0.7(3) . . . . ?
N2 C6 C5 N1 -70.7(3) . . . . ?
N2 C6 C5 C4 108.0(3) . . . . ?
N1 C1 C2 C3 -1.0(4) . . . . ?
N1 C5 C4 C3 -1.0(4) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
C11 C10 C15 O1 178.7(2) . . . . ?
C11 C10 C15 C14 -2.1(4) . . . . ?
C12 C11 C10 C9 -175.9(2) . . . . ?
C12 C11 C10 C15 2.5(4) . . . . ?
C12 C13 C14 C15 1.3(4) . . . . ?
C9 N3 N2 C6 175.0(2) . . . . ?
C9 N3 N2 C7 -1.1(3) . . . . ?
C9 C10 C15 O1 -2.9(4) . . . . ?
C9 C10 C15 C14 176.2(2) . . . . ?
C9 C8 C7 N2 -0.6(3) . . . . ?
C1 N1 C5 C6 -179.5(2) . . . . ?
C1 N1 C5 C4 1.9(4) . . . . ?
C6 N2 C7 C8 -174.7(2) . . . . ?
C6 C5 C4 C3 -179.5(2) . . . . ?
C10 C11 C12 C13 -1.0(4) . . . . ?
C10 C9 C8 C7 179.3(3) . . . . ?
C8 C9 C10 C11 -169.0(3) . . . . ?
C8 C9 C10 C15 12.7(4) . . . . ?
C5 N1 C1 C2 -0.9(4) . . . . ?
C5 C4 C3 C2 -1.0(4) . . . . ?
C7 N2 C6 C5 -111.6(3) . . . . ?
C4 C3 C2 C1 1.9(4) . . . . ?
C13 C14 C15 O1 179.3(3) . . . . ?
C13 C14 C15 C10 0.3(4) . . . . ?
C16 O1 C15 C10 177.1(3) . . . . ?
C16 O1 C15 C14 -2.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
