# 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 2019

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1880296'
_audit_update_record             
;
2018-11-21 deposited with the CCDC.	2019-11-07 downloaded from the CCDC.
;
_audit_creation_date             2018-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H26 Cu2 I2 N12 S2, 2(C2 H3 N)'
_chemical_formula_sum            'C38 H32 Cu2 I2 N14 S2'
_chemical_formula_weight         1129.77
_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'
I I -0.3257 6.8362 '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'
S S 0.3331 0.5567 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8160(3)
_cell_length_b                   10.8974(4)
_cell_length_c                   11.8642(4)
_cell_angle_alpha                105.415(3)
_cell_angle_beta                 107.187(3)
_cell_angle_gamma                94.746(3)
_cell_volume                     1033.52(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6435
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.0120
_cell_measurement_theta_min      4.0700
_shelx_estimated_absorpt_T_max   0.278
_shelx_estimated_absorpt_T_min   0.162
_exptl_absorpt_coefficient_mu    14.333
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             554
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7828
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         4.095
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5281
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -11.00   1.00    1.50    --  -40.36 -57.00  90.00  103
  2  ω    -67.00  36.00   1.00    1.50    --  -40.36  37.00  30.00  103
  3  ω    -70.00  34.00   1.00    1.50    --  -40.36  57.00-120.00  104
  4  ω      1.00  82.00   1.00    1.50    --   40.36 -99.00 -30.00   81
  5  ω     23.00  98.00   1.00    1.50    --   40.36-125.00  30.00   75
  6  ω     24.00 168.00   1.00    4.50    --  106.83 -15.00  30.00  144
  7  ω     23.00 109.00   1.00    4.50    --  106.83 -94.00-120.00   86
  8  ω     29.00 137.00   1.00    4.50    --  106.83 -30.00-150.00  108
  9  ω     23.00 109.00   1.00    4.50    --  106.83 -94.00 120.00   86
 10  ω     29.00 116.00   1.00    4.50    --  106.83-111.00  30.00   87
 11  ω     79.00 178.00   1.00    4.50    --  106.83  45.00  30.00   99
 12  ω     38.00 124.00   1.00    4.50    --  106.83 -61.00  90.00   86
 13  ω     93.00 145.00   1.00    4.50    --  106.83 -92.00-161.00   52
 14  ω    102.00 172.00   1.00    4.50    --  106.83 111.00-150.00   70
 15  ω     76.00 123.00   1.00    4.50    --  106.83 178.00 150.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1848412000
_diffrn_orient_matrix_UB_12      0.0186119000
_diffrn_orient_matrix_UB_13      0.0337882000
_diffrn_orient_matrix_UB_21      0.0184262000
_diffrn_orient_matrix_UB_22      0.0957630000
_diffrn_orient_matrix_UB_23      0.1268642000
_diffrn_orient_matrix_UB_31      0.0031906000
_diffrn_orient_matrix_UB_32      -0.1125515000
_diffrn_orient_matrix_UB_33      0.0559527000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3778
_reflns_number_total             3790
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.062
_refine_diff_density_min         -1.386
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3790
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0495P)²+2.1767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0792
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N5(H5), C16(H16), C3(H3), C15(H15), C11(H11), C9(H9), C4(H4), C17(H17),
 C10(H10), C8(H8), C2(H2), C1(H1), C14(H14)
2.b Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
I2 I 0.22735(2) 0.03550(2) 0.85954(2) 0.01695(9) Uani 1 1 d . . . . .
Cu1 Cu 0.35792(5) 0.27600(4) 0.89877(4) 0.00860(11) Uani 1 1 d . . . . .
S2 S 0.21528(9) 0.28819(7) 0.70685(6) 0.01095(16) Uani 1 1 d . . . . .
N3 N 0.2968(3) 0.4473(2) 0.9552(2) 0.0083(5) Uani 1 1 d . . . . .
N2 N 0.4556(3) 0.3172(2) 1.0854(2) 0.0106(5) Uani 1 1 d . . . . .
N4 N 0.2100(3) 0.5092(2) 0.8789(2) 0.0092(5) Uani 1 1 d . . . . .
N5 N 0.0732(3) 0.4878(2) 0.6750(2) 0.0103(5) Uani 1 1 d . . . . .
H5 H 0.064420 0.449529 0.599398 0.012 Uiso 1 1 calc R . . . .
C12 C 0.1667(4) 0.4396(3) 0.7610(3) 0.0093(6) Uani 1 1 d . . . . .
C6 C 0.3461(3) 0.5058(3) 1.0735(3) 0.0082(6) Uani 1 1 d . . . . .
C16 C -0.2095(4) 0.7716(3) 0.6982(3) 0.0126(6) Uani 1 1 d . . . . .
H16 H -0.281418 0.829467 0.696909 0.015 Uiso 1 1 calc R . . . .
C5 C 0.3070(4) 0.6360(3) 1.1210(3) 0.0087(6) Uani 1 1 d . . . . .
C7 C 0.4336(4) 0.4328(3) 1.1510(3) 0.0093(6) Uani 1 1 d . . . . .
C3 C 0.1137(4) 0.7651(3) 1.1654(3) 0.0145(6) Uani 1 1 d . . . . .
H3 H 0.015942 0.773970 1.178935 0.017 Uiso 1 1 calc R . . . .
C13 C -0.0112(4) 0.5917(3) 0.6928(3) 0.0097(6) Uani 1 1 d . . . . .
C15 C -0.1133(4) 0.7594(3) 0.8090(3) 0.0137(6) Uani 1 1 d . . . . .
H15 H -0.117184 0.811412 0.883843 0.016 Uiso 1 1 calc R . . . .
C11 C 0.5402(4) 0.2450(3) 1.1472(3) 0.0140(6) Uani 1 1 d . . . . .
H11 H 0.557505 0.166442 1.102514 0.017 Uiso 1 1 calc R . . . .
N7 N 0.5689(6) 0.1948(5) 0.5328(4) 0.0462(11) Uani 1 1 d . . . . .
C9 C 0.5748(4) 0.3989(3) 1.3427(3) 0.0153(6) Uani 1 1 d . . . . .
H9 H 0.612610 0.424580 1.428796 0.018 Uiso 1 1 calc R . . . .
C4 C 0.1616(4) 0.6453(3) 1.1420(3) 0.0132(6) Uani 1 1 d . . . . .
H4 H 0.096963 0.572494 1.140434 0.016 Uiso 1 1 calc R . . . .
C17 C -0.1955(4) 0.6953(3) 0.5895(3) 0.0144(6) Uani 1 1 d . . . . .
H17 H -0.256802 0.705714 0.515210 0.017 Uiso 1 1 calc R . . . .
C10 C 0.6027(4) 0.2833(3) 1.2751(3) 0.0165(7) Uani 1 1 d . . . . .
H10 H 0.662794 0.231897 1.315419 0.020 Uiso 1 1 calc R . . . .
C8 C 0.4892(4) 0.4764(3) 1.2794(3) 0.0116(6) Uani 1 1 d . . . . .
H8 H 0.469980 0.555058 1.322232 0.014 Uiso 1 1 calc R . . . .
C2 C 0.2139(4) 0.8707(3) 1.1683(3) 0.0154(6) Uani 1 1 d . . . . .
H2 H 0.183390 0.951629 1.181147 0.018 Uiso 1 1 calc R . . . .
C1 C 0.3614(4) 0.8544(3) 1.1517(3) 0.0151(6) Uani 1 1 d . . . . .
H1 H 0.430539 0.926689 1.157280 0.018 Uiso 1 1 calc R . . . .
C19 C 0.7782(7) 0.0462(5) 0.5067(4) 0.0419(11) Uani 1 1 d . . . . .
H19A H 0.763432 0.010801 0.420168 0.063 Uiso 1 1 calc GR . . . .
H19B H 0.763622 -0.022858 0.540717 0.063 Uiso 1 1 calc GR . . . .
H19C H 0.885080 0.095402 0.549117 0.063 Uiso 1 1 calc GR . . . .
C18 C 0.6609(6) 0.1296(4) 0.5219(4) 0.0323(9) Uani 1 1 d . . . . .
N1 N 0.4086(3) 0.7390(2) 1.1280(2) 0.0098(5) Uani 1 1 d . . . . .
N6 N -0.0980(3) 0.6067(3) 0.5853(2) 0.0126(5) Uani 1 1 d . . . . .
C14 C -0.0112(4) 0.6694(3) 0.8079(3) 0.0121(6) Uani 1 1 d . . . . .
H14 H 0.055513 0.660776 0.881402 0.014 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
I2 Cu1 2.6356(5) . ?
Cu1 S2 2.2977(8) . ?
Cu1 N3 1.985(3) . ?
Cu1 N2 2.031(3) . ?
Cu1 N1 2.186(3) 2_667 ?
S2 C12 1.742(3) . ?
N3 N4 1.364(4) . ?
N3 C6 1.297(4) . ?
N2 C7 1.356(4) . ?
N2 C11 1.339(4) . ?
N4 C12 1.323(4) . ?
N5 C12 1.362(4) . ?
N5 C13 1.409(4) . ?
C6 C5 1.490(4) . ?
C6 C7 1.464(4) . ?
C16 C15 1.385(5) . ?
C16 C17 1.382(5) . ?
C5 C4 1.383(4) . ?
C5 N1 1.345(4) . ?
C7 C8 1.386(4) . ?
C3 C4 1.389(5) . ?
C3 C2 1.378(5) . ?
C13 N6 1.339(4) . ?
C13 C14 1.403(4) . ?
C15 C14 1.385(4) . ?
C11 C10 1.383(5) . ?
N7 C18 1.135(6) . ?
C9 C10 1.386(5) . ?
C9 C8 1.398(4) . ?
C17 N6 1.344(4) . ?
C2 C1 1.390(5) . ?
C1 N1 1.342(4) . ?
C19 C18 1.452(6) . ?

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
S2 Cu1 I2 95.86(2) . . ?
N3 Cu1 I2 134.59(7) . . ?
N3 Cu1 S2 82.52(8) . . ?
N3 Cu1 N2 79.31(10) . . ?
N3 Cu1 N1 120.82(10) . 2_667 ?
N2 Cu1 I2 95.35(7) . . ?
N2 Cu1 S2 161.71(8) . . ?
N2 Cu1 N1 92.58(10) . 2_667 ?
N1 Cu1 I2 104.36(7) 2_667 . ?
N1 Cu1 S2 98.57(7) 2_667 . ?
C12 S2 Cu1 95.71(11) . . ?
N4 N3 Cu1 124.9(2) . . ?
C6 N3 Cu1 117.4(2) . . ?
C6 N3 N4 117.7(3) . . ?
C7 N2 Cu1 114.3(2) . . ?
C11 N2 Cu1 127.1(2) . . ?
C11 N2 C7 118.5(3) . . ?
C12 N4 N3 111.8(2) . . ?
C12 N5 C13 129.0(3) . . ?
N4 C12 S2 125.0(2) . . ?
N4 C12 N5 117.8(3) . . ?
N5 C12 S2 117.1(2) . . ?
N3 C6 C5 119.7(3) . . ?
N3 C6 C7 115.2(3) . . ?
C7 C6 C5 125.0(3) . . ?
C17 C16 C15 118.0(3) . . ?
C4 C5 C6 119.3(3) . . ?
N1 C5 C6 117.3(3) . . ?
N1 C5 C4 123.0(3) . . ?
N2 C7 C6 113.7(3) . . ?
N2 C7 C8 122.6(3) . . ?
C8 C7 C6 123.7(3) . . ?
C2 C3 C4 118.7(3) . . ?
N6 C13 N5 112.1(3) . . ?
N6 C13 C14 122.6(3) . . ?
C14 C13 N5 125.2(3) . . ?
C14 C15 C16 119.7(3) . . ?
N2 C11 C10 122.2(3) . . ?
C10 C9 C8 119.0(3) . . ?
C5 C4 C3 118.8(3) . . ?
N6 C17 C16 123.7(3) . . ?
C11 C10 C9 119.4(3) . . ?
C7 C8 C9 118.2(3) . . ?
C3 C2 C1 118.9(3) . . ?
N1 C1 C2 122.9(3) . . ?
N7 C18 C19 179.5(4) . . ?
C5 N1 Cu1 122.7(2) . 2_667 ?
C1 N1 Cu1 119.9(2) . 2_667 ?
C1 N1 C5 117.5(3) . . ?
C13 N6 C17 117.7(3) . . ?
C15 C14 C13 118.1(3) . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 4.124
_oxdiff_exptl_absorpt_empirical_full_min 0.591
