# 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_1hexane
_database_code_depnum_ccdc_archive 'CCDC 2068700'
loop_
_audit_author_name
_audit_author_address
'Javier Marti-Rujas'
;Politecnico di Milano
Italy
;
_audit_update_record             
;
2021-03-08 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H42 I2 N4 Zn'
_chemical_formula_weight         849.90

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'
N N 0.0061 0.0033 '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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

_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, z'
'-x+1/2, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-x, y-1/2, z-1/2'

_cell_length_a                   14.8749(2)
_cell_length_b                   22.8089(2)
_cell_length_c                   10.34000(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3508.16(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    30957
_cell_measurement_theta_min      1.03768246314
_cell_measurement_theta_max      33.0972094344

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_F_000             1688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    3.558
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.845
_exptl_absorpt_correction_type   cylinder
_exptl_absorpt_correction_T_min  0.8444
_exptl_absorpt_correction_T_max  0.8454
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.82656
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Alba-CELLS, Barcelona, Catalonia, Spain'
_diffrn_measurement_device_type  'CCD Pilatus 6M-Dectris'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            80327
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.1339
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.077
_diffrn_reflns_theta_max         33.662
_diffrn_reflns_theta_full        29.731
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3899
_reflns_number_gt                3502
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1671P)²+23.0326P] 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         3899
_refine_ls_number_parameters     184
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0908
_refine_ls_wR_factor_ref         0.2666
_refine_ls_wR_factor_gt          0.2627
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.070
_refine_ls_shift/su_mean         0.003

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
I I 0.89377(4) 0.83891(2) 0.66218(5) 0.0429(3) Uani 1 1 d . . . . .
Zn Zn 0.81004(8) 0.750000 0.750000 0.0392(4) Uani 1 2 d S T P . .
N1 N 0.7214(4) 0.7226(2) 0.6081(6) 0.0383(13) Uani 1 1 d . . . . .
N2 N 0.5975(5) 0.3704(3) 0.3197(7) 0.0441(16) Uani 1 1 d . . . . .
C4 C 0.6444(5) 0.6450(3) 0.4963(7) 0.0382(15) Uani 1 1 d . . . . .
C9 C 0.6116(5) 0.4601(3) 0.4425(8) 0.0410(16) Uani 1 1 d . . . . .
C6 C 0.6315(5) 0.5806(3) 0.4776(8) 0.0371(14) Uani 1 1 d . . . . .
C12 C 0.6023(5) 0.3957(3) 0.4281(9) 0.0429(17) Uani 1 1 d . . . . .
C13 C 0.5956(6) 0.3063(4) 0.3210(8) 0.0420(18) Uani 1 1 d . . . . .
H13 H 0.595449 0.292024 0.412377 0.050 Uiso 1 1 calc R U . . .
C5 C 0.7051(6) 0.6646(3) 0.5860(8) 0.0399(16) Uani 1 1 d . . . . .
H5 H 0.737375 0.636410 0.635181 0.048 Uiso 1 1 calc R U . . .
C2 C 0.6130(6) 0.7465(4) 0.4482(9) 0.0438(17) Uani 1 1 d . . . . .
H2 H 0.581203 0.775573 0.400973 0.053 Uiso 1 1 calc R U . . .
C14 C 0.5120(6) 0.2840(3) 0.2514(8) 0.0449(17) Uani 1 1 d . . . . .
H14A H 0.511002 0.299348 0.161822 0.054 Uiso 1 1 calc R U . . .
H14B H 0.457525 0.298230 0.296446 0.054 Uiso 1 1 calc R U . . .
C3 C 0.5964(5) 0.6873(4) 0.4258(8) 0.0437(17) Uani 1 1 d . . . . .
H3 H 0.553010 0.675655 0.363475 0.052 Uiso 1 1 calc R U . . .
C11 C 0.6304(6) 0.5437(4) 0.5835(9) 0.0470(18) Uani 1 1 d . . . . .
H11 H 0.636465 0.559149 0.668400 0.056 Uiso 1 1 calc R U . . .
C8 C 0.6118(7) 0.4980(4) 0.3370(8) 0.050(2) Uani 1 1 d . . . . .
H8 H 0.605834 0.482655 0.251988 0.061 Uiso 1 1 calc R U . . .
C1 C 0.6760(6) 0.7625(3) 0.5397(8) 0.0437(17) Uani 1 1 d . . . . .
H1 H 0.687424 0.802955 0.554413 0.052 Uiso 1 1 calc R U . . .
C7 C 0.6207(7) 0.5576(4) 0.3548(9) 0.0489(19) Uani 1 1 d . . . . .
H7 H 0.619333 0.583093 0.282192 0.059 Uiso 1 1 calc R U . . .
C15 C 0.6801(6) 0.2839(3) 0.2515(9) 0.0477(19) Uani 1 1 d . . . . .
H15A H 0.734445 0.298127 0.297194 0.057 Uiso 1 1 calc R U . . .
H15B H 0.681586 0.299378 0.162066 0.057 Uiso 1 1 calc R U . . .
C10 C 0.6201(6) 0.4830(4) 0.5642(9) 0.0457(18) Uani 1 1 d . . . . .
H10 H 0.619002 0.457542 0.636846 0.055 Uiso 1 1 calc R U . . .
CS1 C 0.5804(15) 0.9224(9) 0.5455(19) 0.120(6) Uiso 1 1 d . . . . .
HS1A H 0.515673 0.930041 0.549119 0.180 Uiso 1 1 calc R U . . .
HS1B H 0.594671 0.900961 0.465909 0.180 Uiso 1 1 calc R U . . .
HS1C H 0.598234 0.898800 0.620522 0.180 Uiso 1 1 calc R U . . .
CS3 C 0.726(2) 0.9715(9) 0.542(4) 0.253(19) Uiso 1 1 d D . . . .
HS3A H 0.742186 0.949459 0.462773 0.303 Uiso 1 1 calc R U . . .
HS3B H 0.745880 0.948132 0.617359 0.303 Uiso 1 1 calc R U . . .
CS2 C 0.629(2) 0.9780(14) 0.547(3) 0.178(11) Uiso 1 1 d D . . . .
HS2A H 0.609646 1.001820 0.472146 0.214 Uiso 1 1 calc R U . . .
HS2B H 0.613204 0.999662 0.626576 0.214 Uiso 1 1 calc R U . . .
HX H 0.606(4) 0.368(3) 0.500(6) 0.009(14) Uiso 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
I Zn 2.5473(8) . ?
Zn N1 2.070(6) . ?
Zn N1 2.070(6) 4_566 ?
N1 C1 1.336(10) . ?
N1 C5 1.364(8) . ?
N2 C12 1.263(11) . ?
N2 C13 1.461(12) . ?
C4 C5 1.369(11) . ?
C4 C3 1.404(11) . ?
C4 C6 1.494(10) . ?
C9 C10 1.368(12) . ?
C9 C8 1.391(13) . ?
C9 C12 1.483(11) . ?
C6 C11 1.382(12) . ?
C6 C7 1.383(12) . ?
C12 HX 0.97(7) . ?
C13 C14 1.524(11) . ?
C13 C15 1.536(12) . ?
C13 H13 1.0000 . ?
C5 H5 0.9500 . ?
C2 C1 1.382(12) . ?
C2 C3 1.391(12) . ?
C2 H2 0.9500 . ?
C14 C14 1.552(15) 4 ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C3 H3 0.9500 . ?
C11 C10 1.407(11) . ?
C11 H11 0.9500 . ?
C8 C7 1.378(12) . ?
C8 H8 0.9500 . ?
C1 H1 0.9500 . ?
C7 H7 0.9500 . ?
C15 C15 1.549(16) 4 ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C10 H10 0.9500 . ?
CS1 CS2 1.46(4) . ?
CS1 HS1A 0.9800 . ?
CS1 HS1B 0.9800 . ?
CS1 HS1C 0.9800 . ?
CS3 CS2 1.445(19) . ?
CS3 CS3 1.49(2) 2_675 ?
CS3 HS3A 0.9900 . ?
CS3 HS3B 0.9900 . ?
CS2 HS2A 0.9900 . ?
CS2 HS2B 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 Zn N1 100.8(4) . 4_566 ?
N1 Zn I 107.43(18) . . ?
N1 Zn I 108.88(16) 4_566 . ?
N1 Zn I 108.89(16) . 4_566 ?
N1 Zn I 107.44(18) 4_566 4_566 ?
I Zn I 121.45(6) . 4_566 ?
C1 N1 C5 118.9(7) . . ?
C1 N1 Zn 119.4(5) . . ?
C5 N1 Zn 121.7(5) . . ?
C12 N2 C13 116.8(7) . . ?
C5 C4 C3 117.6(7) . . ?
C5 C4 C6 119.5(7) . . ?
C3 C4 C6 122.9(7) . . ?
C10 C9 C8 119.0(7) . . ?
C10 C9 C12 118.6(8) . . ?
C8 C9 C12 122.4(8) . . ?
C11 C6 C7 119.7(7) . . ?
C11 C6 C4 119.9(7) . . ?
C7 C6 C4 120.5(7) . . ?
N2 C12 C9 123.2(8) . . ?
N2 C12 HX 113(4) . . ?
C9 C12 HX 124(4) . . ?
N2 C13 C14 110.2(7) . . ?
N2 C13 C15 108.2(7) . . ?
C14 C13 C15 109.6(7) . . ?
N2 C13 H13 109.6 . . ?
C14 C13 H13 109.6 . . ?
C15 C13 H13 109.6 . . ?
N1 C5 C4 123.1(7) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C1 C2 C3 119.4(8) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C13 C14 C14 110.1(6) . 4 ?
C13 C14 H14A 109.6 . . ?
C14 C14 H14A 109.6 4 . ?
C13 C14 H14B 109.6 . . ?
C14 C14 H14B 109.6 4 . ?
H14A C14 H14B 108.2 . . ?
C2 C3 C4 119.3(8) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C6 C11 C10 119.2(8) . . ?
C6 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C7 C8 C9 120.5(8) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
N1 C1 C2 121.6(7) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C8 C7 C6 120.6(8) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C13 C15 C15 110.0(6) . 4 ?
C13 C15 H15A 109.7 . . ?
C15 C15 H15A 109.7 4 . ?
C13 C15 H15B 109.7 . . ?
C15 C15 H15B 109.7 4 . ?
H15A C15 H15B 108.2 . . ?
C9 C10 C11 121.1(8) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
CS2 CS1 HS1A 109.4 . . ?
CS2 CS1 HS1B 109.5 . . ?
HS1A CS1 HS1B 109.5 . . ?
CS2 CS1 HS1C 109.5 . . ?
HS1A CS1 HS1C 109.5 . . ?
HS1B CS1 HS1C 109.5 . . ?
CS2 CS3 CS3 113(4) . 2_675 ?
CS2 CS3 HS3A 109.0 . . ?
CS3 CS3 HS3A 109.0 2_675 . ?
CS2 CS3 HS3B 109.0 . . ?
CS3 CS3 HS3B 108.9 2_675 . ?
HS3A CS3 HS3B 107.8 . . ?
CS3 CS2 CS1 114(2) . . ?
CS3 CS2 HS2A 108.7 . . ?
CS1 CS2 HS2A 108.8 . . ?
CS3 CS2 HS2B 108.8 . . ?
CS1 CS2 HS2B 108.8 . . ?
HS2A CS2 HS2B 107.7 . . ?

_refine_diff_density_max         3.806
_refine_diff_density_min         -1.688
_refine_diff_density_rms         0.273


# start Validation Reply Form
_vrf_PLAT971_1hexane             
;
PROBLEM: Check Calcd Resid. Dens.  0.76A   From I               3.69 eA-3  
RESPONSE: This is due to the synchrotron data.
;
