# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_sjkc21aj08
_database_code_depnum_ccdc_archive 'CCDC 2091146'
loop_
_audit_author_name
_audit_author_address
'Jack Clegg'
;The University of Queensalnd
Australia
;
_audit_update_record             
;
2021-06-21 deposited with the CCDC.	2021-08-04 downloaded from the CCDC.
;
_audit_creation_date             2021-06-18
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C6 H5 Cl2 I), Cl, C8 H20 N'
_chemical_formula_sum            'C20 H30 Cl5 I2 N'
_chemical_formula_weight         715.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H16 I Cl3 N'
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'
Cl Cl 0.1484 0.1585 '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'

_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, 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                   9.8786(4)
_cell_length_b                   17.2644(6)
_cell_length_c                   15.6853(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.359(4)
_cell_angle_gamma                90
_cell_volume                     2622.70(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10950
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.9130
_cell_measurement_theta_min      2.3860
_shelx_estimated_absorpt_T_max   0.868
_shelx_estimated_absorpt_T_min   0.669
_exptl_absorpt_coefficient_mu    2.916
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16675
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         2.411
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  11.00   0.50    2.50    --    8.20  91.00 145.00   72
  2  ω     16.00  42.00   0.50    2.50    --    8.20  91.00 145.00   52
  3  ω    -16.00  69.00   0.50    2.50    --    8.20  77.00 -90.00  170
  4  ω    -13.00  34.00   0.50    2.50    --    8.20 -91.00  32.00   94
  5  ω     -1.00  45.00   0.50    2.50    --    8.20 -99.00 120.00   92
  6  ω     11.00  45.00   0.50    2.50    --    8.20 -99.00 -30.00   68
  7  ω    -65.00 -11.00   0.50    2.50    --    8.20 -57.00 -30.00  108
  8  ω    -37.00 -12.00   0.50    2.50    --   -9.76 -57.00 -30.00   50
  9  ω    -80.00 -55.00   0.50    2.50    --   -9.76 -57.00 -30.00   50
 10  ω     -1.00  24.00   0.50    2.50    --   -9.76  91.00 145.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0347861000
_diffrn_orient_matrix_UB_12      -0.0007783000
_diffrn_orient_matrix_UB_13      0.0441144000
_diffrn_orient_matrix_UB_21      0.0256940000
_diffrn_orient_matrix_UB_22      -0.0374998000
_diffrn_orient_matrix_UB_23      -0.0062858000
_diffrn_orient_matrix_UB_31      0.0591004000
_diffrn_orient_matrix_UB_32      0.0167542000
_diffrn_orient_matrix_UB_33      -0.0119537000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2902
_reflns_number_total             3242
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.775
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         3242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0239
_refine_ls_restrained_S_all      1.048
_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)+(0.0158P)²+6.5299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0493
_refine_ls_wR_factor_ref         0.0506
_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:
 C7(H7A,H7B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C3(H3), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C8(H8A,H8B,H8C)
;
_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 0.70275(2) 0.67420(2) 0.86121(2) 0.01521(5) Uani 1 1 d . . . . .
Cl1 Cl 0.52188(7) 0.76362(4) 0.78240(4) 0.02340(14) Uani 1 1 d . . . . .
Cl2 Cl 0.87979(6) 0.57775(4) 0.93042(4) 0.02206(13) Uani 1 1 d . . . . .
Cl3 Cl 0.750000 0.80487(6) 1.000000 0.0354(3) Uani 1 2 d S T P . .
N1 N 0.750000 0.24350(17) 0.500000 0.0159(6) Uani 1 2 d S T P . .
C1 C 0.6298(2) 0.59005(13) 0.76549(16) 0.0150(5) Uani 1 1 d . . . . .
C6 C 0.5554(3) 0.52909(14) 0.79073(17) 0.0188(5) Uani 1 1 d . . . . .
H6 H 0.541230 0.525198 0.848747 0.023 Uiso 1 1 calc R U . . .
C7 C 0.8502(3) 0.29289(16) 0.56313(18) 0.0216(5) Uani 1 1 d . . . . .
H7A H 0.910904 0.258267 0.604212 0.026 Uiso 1 1 calc R U . . .
H7B H 0.909331 0.321910 0.530093 0.026 Uiso 1 1 calc R U . . .
C9 C 0.8381(3) 0.19378(15) 0.45222(18) 0.0211(5) Uani 1 1 d . . . . .
H9A H 0.892797 0.228437 0.421735 0.025 Uiso 1 1 calc R U . . .
H9B H 0.904024 0.163931 0.495738 0.025 Uiso 1 1 calc R U . . .
C2 C 0.6539(3) 0.59770(15) 0.68170(17) 0.0192(5) Uani 1 1 d . . . . .
H2 H 0.706147 0.639911 0.666501 0.023 Uiso 1 1 calc R U . . .
C10 C 0.7589(3) 0.13756(18) 0.3866(2) 0.0321(7) Uani 1 1 d . . . . .
H10A H 0.696360 0.166440 0.341364 0.048 Uiso 1 1 calc R U . . .
H10B H 0.705189 0.102302 0.415919 0.048 Uiso 1 1 calc R U . . .
H10C H 0.823950 0.107593 0.359951 0.048 Uiso 1 1 calc R U . . .
C3 C 0.5996(3) 0.54197(16) 0.62066(18) 0.0228(6) Uani 1 1 d . . . . .
H3 H 0.614536 0.545837 0.562807 0.027 Uiso 1 1 calc R U . . .
C5 C 0.5022(3) 0.47378(15) 0.72878(18) 0.0221(5) Uani 1 1 d . . . . .
H5 H 0.451120 0.431237 0.744416 0.027 Uiso 1 1 calc R U . . .
C8 C 0.7825(3) 0.35009(18) 0.6149(2) 0.0310(7) Uani 1 1 d . . . . .
H8A H 0.730591 0.388477 0.575481 0.047 Uiso 1 1 calc R U . . .
H8B H 0.853706 0.376344 0.657479 0.047 Uiso 1 1 calc R U . . .
H8C H 0.719493 0.322430 0.645364 0.047 Uiso 1 1 calc R U . . .
C4 C 0.5233(3) 0.48043(16) 0.64394(18) 0.0254(6) Uani 1 1 d . . . . .
H4 H 0.485433 0.442815 0.601715 0.030 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
I1 Cl1 2.4967(7) . ?
I1 Cl2 2.5024(6) . ?
I1 C1 2.111(2) . ?
N1 C7 1.517(3) . ?
N1 C7 1.517(3) 2_656 ?
N1 C9 1.521(3) . ?
N1 C9 1.521(3) 2_656 ?
C1 C6 1.385(3) . ?
C1 C2 1.387(4) . ?
C6 C5 1.390(4) . ?
C7 C8 1.515(4) . ?
C9 C10 1.516(4) . ?
C2 C3 1.389(4) . ?
C3 C4 1.392(4) . ?
C5 C4 1.392(4) . ?

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
Cl1 I1 Cl2 175.61(2) . . ?
C1 I1 Cl1 87.87(7) . . ?
C1 I1 Cl2 87.82(6) . . ?
C7 N1 C7 111.6(3) . 2_656 ?
C7 N1 C9 106.01(14) 2_656 2_656 ?
C7 N1 C9 106.00(14) . . ?
C7 N1 C9 111.03(14) . 2_656 ?
C7 N1 C9 111.03(14) 2_656 . ?
C9 N1 C9 111.3(3) . 2_656 ?
C6 C1 I1 116.45(18) . . ?
C6 C1 C2 122.9(2) . . ?
C2 C1 I1 120.66(18) . . ?
C1 C6 C5 118.1(2) . . ?
C8 C7 N1 114.6(2) . . ?
C10 C9 N1 115.3(2) . . ?
C1 C2 C3 118.2(2) . . ?
C2 C3 C4 120.2(3) . . ?
C6 C5 C4 120.3(2) . . ?
C5 C4 C3 120.3(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.328
_oxdiff_exptl_absorpt_empirical_full_min 0.817
