# 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 2022

####################################################################### 
# 
# 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_UM3483b
_database_code_depnum_ccdc_archive 'CCDC 2114714'
loop_
_audit_author_name
_audit_author_address
'Peter Y. Zavalij'
;University of Maryland
United States of America
;
_audit_update_record             
;
2021-10-08 deposited with the CCDC.	2021-12-07 downloaded from the CCDC.
;
_audit_creation_date             2021-08-16
_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_systematic        ?
_chemical_formula_moiety         'C14 H30 N2, 2(I)'
_chemical_formula_sum            'C14 H30 I2 N2'
_chemical_formula_weight         480.20
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'

_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                   6.5208(2)
_cell_length_b                   14.5116(5)
_cell_length_c                   10.1283(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.2182(5)
_cell_angle_gamma                90
_cell_volume                     929.05(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10015
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.0
_cell_measurement_theta_min      2.5
_shelx_estimated_absorpt_T_max   0.486
_shelx_estimated_absorpt_T_min   0.283
_exptl_absorpt_coefficient_mu    3.375
_exptl_absorpt_correction_T_max  0.430
_exptl_absorpt_correction_T_min  0.303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Krause et al, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16743
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.248
_diffrn_reflns_theta_min         2.505
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      -0.0559613
_diffrn_orient_matrix_UB_12      0.0008476
_diffrn_orient_matrix_UB_13      0.0834930
_diffrn_orient_matrix_UB_21      0.0225305
_diffrn_orient_matrix_UB_22      0.0681498
_diffrn_orient_matrix_UB_23      0.0076005
_diffrn_orient_matrix_UB_31      -0.1462490
_diffrn_orient_matrix_UB_32      0.0101746
_diffrn_orient_matrix_UB_33      -0.0578387
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2779
_reflns_number_total             3037
_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       'Apex2, Saint (Bruker, 2012)'
_computing_data_collection       'Apex2 (Bruker, 2012)'
_computing_data_reduction        'Apex2, Saint'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015c)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         1.214
_refine_diff_density_min         -1.103
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.0284(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         3037
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0240
_refine_ls_restrained_S_all      1.056
_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)+(0.0181P)²+0.9586P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0539
_refine_ls_wR_factor_ref         0.0553
_refine_special_details          
;
H atoms were positioned from the geometric considerations and refined
as riding on the attached atoms with Uiso constrained to be 20% (50%
for methyl group) larger than Ueqv of the attached group. Orientation
of methyl groups was optimized.
;
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C4(H4)
1.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C3(H3A,H3B), C2(H2A,H2B)
1.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.89162(2) 0.84473(2) 0.65652(2) 0.04148(7) Uani 1 1 d . . . . .
N1 N 0.3572(3) 0.62374(12) 0.78449(17) 0.0313(3) Uani 1 1 d . . . . .
C5 C 0.2873(3) 0.58592(16) 0.5339(2) 0.0368(4) Uani 1 1 d . . . . .
H5A H 0.354643 0.642013 0.513777 0.044 Uiso 1 1 calc R U . . .
H5B H 0.174816 0.570692 0.454736 0.044 Uiso 1 1 calc R U . . .
C7 C 0.2493(4) 0.62752(19) 0.8995(2) 0.0455(5) Uani 1 1 d . . . . .
H7A H 0.351673 0.641049 0.982935 0.068 Uiso 1 1 calc R U . . .
H7B H 0.184176 0.569127 0.907349 0.068 Uiso 1 1 calc R U . . .
H7C H 0.143122 0.674812 0.881570 0.068 Uiso 1 1 calc R U . . .
C4 C 0.4501(3) 0.50783(14) 0.56055(19) 0.0308(4) Uani 1 1 d . . . . .
H4 H 0.377433 0.451004 0.575005 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1928(3) 0.60279(16) 0.6546(2) 0.0351(4) Uani 1 1 d . . . . .
H6A H 0.094589 0.654020 0.633755 0.042 Uiso 1 1 calc R U . . .
H6B H 0.113437 0.548681 0.668738 0.042 Uiso 1 1 calc R U . . .
C3 C 0.6173(3) 0.52955(16) 0.6923(2) 0.0359(4) Uani 1 1 d . . . . .
H3A H 0.715190 0.478275 0.714159 0.043 Uiso 1 1 calc R U . . .
H3B H 0.696889 0.583517 0.678045 0.043 Uiso 1 1 calc R U . . .
C2 C 0.5197(3) 0.54706(15) 0.8118(2) 0.0347(4) Uani 1 1 d . . . . .
H2A H 0.452852 0.490879 0.832057 0.042 Uiso 1 1 calc R U . . .
H2B H 0.631034 0.562805 0.891279 0.042 Uiso 1 1 calc R U . . .
C8 C 0.4610(4) 0.71506(16) 0.7770(3) 0.0437(5) Uani 1 1 d . . . . .
H8A H 0.533161 0.713791 0.705011 0.066 Uiso 1 1 calc R U . . .
H8B H 0.560896 0.727283 0.861987 0.066 Uiso 1 1 calc R U . . .
H8C H 0.355417 0.762601 0.759129 0.066 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.03553(9) 0.03862(9) 0.04778(10) 0.00320(6) 0.00546(6) 0.00413(5)
N1 0.0320(8) 0.0311(8) 0.0322(8) -0.0012(6) 0.0108(6) 0.0000(6)
C5 0.0316(9) 0.0453(11) 0.0315(9) 0.0006(8) 0.0040(7) 0.0117(8)
C7 0.0518(13) 0.0506(13) 0.0403(11) -0.0048(10) 0.0234(10) 0.0023(11)
C4 0.0276(8) 0.0356(9) 0.0284(8) 0.0011(7) 0.0055(6) 0.0060(7)
C6 0.0259(8) 0.0406(11) 0.0376(10) -0.0044(8) 0.0059(7) 0.0040(7)
C3 0.0295(8) 0.0452(11) 0.0306(9) 0.0000(8) 0.0032(7) 0.0098(8)
C2 0.0368(9) 0.0363(10) 0.0295(8) 0.0023(7) 0.0054(7) 0.0059(8)
C8 0.0446(11) 0.0319(10) 0.0543(13) -0.0026(9) 0.0115(10) -0.0065(9)

_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
N1 C7 1.502(3) . ?
N1 C6 1.510(3) . ?
N1 C2 1.514(3) . ?
N1 C8 1.498(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.531(3) . ?
C5 C6 1.518(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C4 C4 1.540(4) 3_666 ?
C4 H4 0.9800 . ?
C4 C3 1.534(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.520(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
C7 N1 C6 108.35(17) . . ?
C7 N1 C2 108.99(17) . . ?
C6 N1 C2 109.04(15) . . ?
C8 N1 C7 108.08(18) . . ?
C8 N1 C6 111.52(17) . . ?
C8 N1 C2 110.78(17) . . ?
H5A C5 H5B 107.9 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C6 C5 C4 112.24(17) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C4 C4 112.3(2) . 3_666 ?
C5 C4 H4 108.0 . . ?
C5 C4 C3 108.36(17) . . ?
C4 C4 H4 108.0 3_666 . ?
C3 C4 C4 112.01(19) . 3_666 ?
C3 C4 H4 108.0 . . ?
N1 C6 C5 113.08(16) . . ?
N1 C6 H6A 109.0 . . ?
N1 C6 H6B 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C2 C3 C4 112.33(16) . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
N1 C2 C3 112.87(16) . . ?
N1 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
C5 C4 C3 C2 54.4(2) . . . . ?
C7 N1 C6 C5 -173.10(19) . . . . ?
C7 N1 C2 C3 172.50(19) . . . . ?
C4 C5 C6 N1 56.8(3) . . . . ?
C4 C4 C3 C2 178.8(2) 3_666 . . . ?
C4 C3 C2 N1 -56.5(2) . . . . ?
C6 N1 C2 C3 54.4(2) . . . . ?
C6 C5 C4 C4 -178.7(2) . . . 3_666 ?
C6 C5 C4 C3 -54.4(2) . . . . ?
C2 N1 C6 C5 -54.6(2) . . . . ?
C8 N1 C6 C5 68.1(2) . . . . ?
C8 N1 C2 C3 -68.7(2) . . . . ?

_shelx_res_file                  
;
TITL b in P2(1)/c
    b.res
    created by SHELXL-2018/3 at 15:39:54 on 14-Aug-2021
CELL 0.71073   6.52080  14.51160  10.12830  90.0000 104.2182  90.0000
ZERR    2.00   0.00020   0.00050   0.00030   0.0000   0.0005   0.0000
LATT 1
SYMM -X, 1/2+Y, 1/2-Z
SFAC C  H  N  I
UNIT 28 60  4 4
OMIT  -2.00  62.5
L.S. 10
ACTA
BOND $H
CONF
FMAP 2
PLAN 20
SIZE 0.25 0.42 0.50
TEMP 23.000
WGHT    0.018120    0.958600
EXTI    0.028403
FVAR       0.20269
I1    4    0.891618    0.844726    0.656522    11.00000    0.03553    0.03862 =
         0.04778    0.00320    0.00546    0.00413
N1    3    0.357244    0.623741    0.784494    11.00000    0.03203    0.03111 =
         0.03216   -0.00117    0.01077   -0.00002
C5    1    0.287316    0.585917    0.533899    11.00000    0.03156    0.04535 =
         0.03150    0.00058    0.00396    0.01171
AFIX  23
H5A   2    0.354643    0.642013    0.513777    11.00000   -1.20000
H5B   2    0.174816    0.570692    0.454736    11.00000   -1.20000
AFIX   0
C7    1    0.249314    0.627523    0.899462    11.00000    0.05180    0.05056 =
         0.04033   -0.00480    0.02337    0.00232
AFIX 137
H7A   2    0.351673    0.641049    0.982935    11.00000   -1.50000
H7B   2    0.184176    0.569127    0.907349    11.00000   -1.50000
H7C   2    0.143122    0.674812    0.881570    11.00000   -1.50000
AFIX   0
C4    1    0.450143    0.507833    0.560553    11.00000    0.02764    0.03561 =
         0.02845    0.00105    0.00547    0.00595
AFIX  13
H4    2    0.377433    0.451004    0.575005    11.00000   -1.20000
AFIX   0
C6    1    0.192775    0.602786    0.654618    11.00000    0.02594    0.04058 =
         0.03765   -0.00444    0.00591    0.00401
AFIX  23
H6A   2    0.094589    0.654020    0.633755    11.00000   -1.20000
H6B   2    0.113437    0.548681    0.668738    11.00000   -1.20000
AFIX   0
C3    1    0.617260    0.529547    0.692341    11.00000    0.02952    0.04520 =
         0.03064   -0.00005    0.00317    0.00985
AFIX  23
H3A   2    0.715190    0.478275    0.714159    11.00000   -1.20000
H3B   2    0.696889    0.583517    0.678045    11.00000   -1.20000
AFIX   0
C2    1    0.519677    0.547062    0.811755    11.00000    0.03677    0.03634 =
         0.02951    0.00228    0.00540    0.00589
AFIX  23
H2A   2    0.452852    0.490879    0.832057    11.00000   -1.20000
H2B   2    0.631034    0.562805    0.891279    11.00000   -1.20000
AFIX   0
C8    1    0.460998    0.715055    0.776980    11.00000    0.04462    0.03195 =
         0.05432   -0.00261    0.01149   -0.00652
AFIX 137
H8A   2    0.533161    0.713791    0.705011    11.00000   -1.50000
H8B   2    0.560896    0.727283    0.861987    11.00000   -1.50000
H8C   2    0.355417    0.762601    0.759129    11.00000   -1.50000
AFIX   0
HKLF 4




REM  b in P2(1)/c
REM wR2 = 0.055252, GooF = S = 1.05558, Restrained GooF = 1.05558 for all data
REM R1 = 0.024016 for 2779 Fo > 4sig(Fo) and 0.026803 for all 3037 data
REM 85 parameters refined using 0 restraints

END

WGHT      0.0214      0.8592

REM Highest difference peak  1.214,  deepest hole -1.103,  1-sigma level  0.072
Q1    1   0.8525  0.8124  0.6085  11.00000  0.05    1.21
Q2    1   0.8645  0.8415  0.7175  11.00000  0.05    0.92
Q3    1   0.9345  0.8724  0.6376  11.00000  0.05    0.36
Q4    1   0.1104  0.7210  0.8455  11.00000  0.05    0.28
Q5    1   0.2944  0.6167  0.8415  11.00000  0.05    0.28
Q6    1   0.5298  0.5174  0.6205  11.00000  0.05    0.26
Q7    1   0.5000  0.5000  0.5000  10.50000  0.05    0.26
Q8    1   0.5609  0.5365  0.7417  11.00000  0.05    0.25
Q9    1   0.9864  0.8863  0.7339  11.00000  0.05    0.25
Q10   1   0.2546  0.5950  0.6066  11.00000  0.05    0.24
Q11   1   0.4292  0.6582  0.7808  11.00000  0.05    0.24
Q12   1   0.3806  0.5456  0.5413  11.00000  0.05    0.23
Q13   1   0.7372  0.7997  0.5390  11.00000  0.05    0.23
Q14   1   0.7054  0.8156  0.5459  11.00000  0.05    0.21
Q15   1   0.2612  0.6229  0.7315  11.00000  0.05    0.21
Q16   1   0.9058  0.4120  0.7343  11.00000  0.05    0.20
Q17   1   0.1670  0.5302  0.7062  11.00000  0.05    0.20
Q18   1   1.0850  0.7990  0.7600  11.00000  0.05    0.20
Q19   1   0.4953  0.5276  0.8826  11.00000  0.05    0.18
Q20   1   0.6497  0.8661  0.5748  11.00000  0.05    0.18
;
_shelx_res_checksum              4695
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
