# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_al153
_database_code_depnum_ccdc_archive 'CCDC 1991665'
loop_
_audit_author_name
_audit_author_address
'Christopher Pask'
;University of Leeds
United Kingdom
;
_audit_update_record             
;
2020-03-20 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_audit_creation_date             2019-08-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 I N3 O'
_chemical_formula_sum            'C12 H12 I N3 O'
_chemical_formula_weight         341.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24  H24  I2  N6  O2  '
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'
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'
O O 0.0492 0.0322 '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                   4.1678(4)
_cell_length_b                   10.6544(9)
_cell_length_c                   14.6694(12)
_cell_angle_alpha                73.012(7)
_cell_angle_beta                 84.892(7)
_cell_angle_gamma                78.774(8)
_cell_volume                     610.70(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2802
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      73.1020
_cell_measurement_theta_min      6.2990
_shelx_estimated_absorpt_T_max   0.328
_shelx_estimated_absorpt_T_min   0.093
_exptl_absorpt_coefficient_mu    20.504
_exptl_absorpt_correction_T_max  0.467
_exptl_absorpt_correction_T_min  0.153
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.855
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -3 -9 0.0372
0 3 9 0.0372
3 -1 2 0.0965
-3 1 -2 0.0965
0 -6 1 0.0276
0 7 0 0.0649

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.1025 -2.7265 -9.3566 0.0000 1.0000 -0.0000
-0.1025 2.7265 9.3566 -0.0000 -1.0000 0.0000
2.5737 -0.5126 1.5420 0.4226 -0.0000 0.9063
-2.5737 0.5126 -1.5420 -0.4226 0.0000 -0.9063
-0.1081 -6.4376 0.5101 0.9829 0.0779 -0.1670
0.2970 6.5753 -0.1104 -0.9654 -0.1103 0.2365

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3920
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.301
_diffrn_reflns_theta_min         4.409
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00 -22.00   1.00    1.00    --  -38.50 -64.00 -75.48   34
  2  ω    -63.00 -34.00   1.00    1.00    --  -38.50  57.00 -60.00   29
  3  ω   -101.00  -8.00   1.00    1.00    --  -38.50 -19.00   0.00   93
  4  ω    -45.00 -14.00   1.00    1.00    --  -38.50  38.00-180.00   31
  5  ω    -44.00 -14.00   1.00    1.00    --  -38.50 -57.00 -60.00   30
  6  ω     17.00  48.00   1.00    1.00    --   42.96  65.00-136.02   31
  7  ω     17.00  87.00   1.00    1.00    --   42.96  64.00 141.10   70
  8  ω     19.00  62.00   1.00    1.00    --   42.96  65.00 -55.66   43
  9  ω     53.00  80.00   1.00    1.00    --  103.73 -61.00 -60.00   27
 10  ω     84.00 114.00   1.00    1.00    --  103.73  30.00 120.00   30
 11  ω     83.00 150.00   1.00    1.00    --  103.73  30.00 -60.00   67
 12  ω    146.00 175.00   1.00    1.00    --  103.73  30.00 120.00   29
 13  ω     71.00  98.00   1.00    1.00    --  103.73 -65.00  63.27   27
 14  ω     62.00 108.00   1.00    1.00    --  103.73 -64.00 153.08   46
 15  ω     30.00 124.00   1.00    1.00    --  103.73 -30.00 120.00   94
 16  ω     96.00 122.00   1.00    1.00    --  103.73  45.00 150.00   26
 17  ω     31.00 124.00   1.00    1.00    --  103.73 -30.00 -60.00   93
 18  ω     39.00 110.00   1.00    1.00    --  103.73 -65.00  81.42   71
 19  ω     59.00 116.00   1.00    1.00    --  103.73 -65.00-134.73   57
 20  ω     47.00  98.00   1.00    1.00    --  103.73 -65.00   0.31   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1071055000
_diffrn_orient_matrix_UB_12      -0.1508975000
_diffrn_orient_matrix_UB_13      0.0451438000
_diffrn_orient_matrix_UB_21      0.0558305000
_diffrn_orient_matrix_UB_22      -0.0209723000
_diffrn_orient_matrix_UB_23      -0.1001539000
_diffrn_orient_matrix_UB_31      0.3572031000
_diffrn_orient_matrix_UB_32      0.0197977000
_diffrn_orient_matrix_UB_33      -0.0018568000
_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                2200
_reflns_number_total             2275
_reflns_odcompleteness_completeness 97.42
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.313
_refine_diff_density_min         -1.169
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.093
_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)+(0.0562P)²+0.5264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0880
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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 -0.13185(6) 0.75387(2) 0.75990(2) 0.02257(12) Uani 1 1 d . . . . .
O1 O 0.5799(8) 0.9244(3) 0.3935(2) 0.0264(7) Uani 1 1 d . . . . .
N1 N -0.1391(10) 0.5320(3) 0.6260(3) 0.0216(7) Uani 1 1 d . . . . .
N2 N 0.1492(9) 0.6596(3) 0.4974(2) 0.0192(7) Uani 1 1 d . . . . .
N3 N 0.2858(9) 0.7729(3) 0.4845(2) 0.0186(7) Uani 1 1 d . . . . .
C1 C 0.0080(10) 0.6400(4) 0.5841(3) 0.0202(8) Uani 1 1 d . . . . .
C2 C 0.0495(10) 0.7408(4) 0.6267(3) 0.0194(8) Uani 1 1 d . . . . .
C3 C 0.2258(11) 0.8226(4) 0.5615(3) 0.0205(8) Uani 1 1 d . . . . .
H3 H 0.2925 0.8978 0.5681 0.025 Uiso 1 1 calc R . . . .
C4 C 0.4506(10) 0.8288(4) 0.3996(3) 0.0203(8) Uani 1 1 d . . . . .
C5 C 0.4547(11) 0.7638(4) 0.3216(3) 0.0211(8) Uani 1 1 d . . . . .
H5A H 0.2389 0.7445 0.3181 0.025 Uiso 1 1 calc R . . . .
H5B H 0.6074 0.6800 0.3367 0.025 Uiso 1 1 calc R . . . .
C6 C 0.5538(11) 0.8524(4) 0.2242(3) 0.0227(8) Uani 1 1 d . . . . .
H6A H 0.4096 0.9384 0.2109 0.027 Uiso 1 1 calc R . . . .
H6B H 0.7751 0.8670 0.2264 0.027 Uiso 1 1 calc R . . . .
C7 C 0.5371(10) 0.7907(4) 0.1448(3) 0.0204(8) Uani 1 1 d . . . . .
C8 C 0.3531(11) 0.8583(4) 0.0656(3) 0.0250(9) Uani 1 1 d . . . . .
H8 H 0.2338 0.9429 0.0622 0.030 Uiso 1 1 calc R . . . .
C9 C 0.3411(12) 0.8037(5) -0.0086(3) 0.0289(10) Uani 1 1 d . . . . .
H9 H 0.2195 0.8525 -0.0617 0.035 Uiso 1 1 calc R . . . .
C10 C 0.5108(12) 0.6758(5) -0.0038(3) 0.0282(10) Uani 1 1 d . . . . .
H10 H 0.4991 0.6377 -0.0527 0.034 Uiso 1 1 calc R . . . .
C11 C 0.6973(13) 0.6064(4) 0.0747(3) 0.0294(10) Uani 1 1 d . . . . .
H11 H 0.8144 0.5215 0.0782 0.035 Uiso 1 1 calc R . . . .
C12 C 0.7110(12) 0.6626(4) 0.1488(3) 0.0262(9) Uani 1 1 d . . . . .
H12 H 0.8365 0.6147 0.2012 0.031 Uiso 1 1 calc R . . . .
H1A H -0.300(15) 0.547(6) 0.664(4) 0.031(14) Uiso 1 1 d . . . . .
H1B H -0.188(14) 0.485(6) 0.588(4) 0.031(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
I1 C2 2.065(4) . ?
O1 C4 1.220(5) . ?
N1 C1 1.368(5) . ?
N1 H1A 0.86(6) . ?
N1 H1B 0.90(6) . ?
N2 N3 1.390(4) . ?
N2 C1 1.330(5) . ?
N3 C3 1.366(5) . ?
N3 C4 1.397(5) . ?
C1 C2 1.434(5) . ?
C2 C3 1.361(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.497(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.537(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.508(6) . ?
C7 C8 1.382(6) . ?
C7 C12 1.402(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.385(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.392(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.395(7) . ?
C12 H12 0.9300 . ?

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
C1 N1 H1A 114(4) . . ?
C1 N1 H1B 118(4) . . ?
H1A N1 H1B 111(5) . . ?
C1 N2 N3 104.2(3) . . ?
N2 N3 C4 121.8(3) . . ?
C3 N3 N2 112.1(3) . . ?
C3 N3 C4 126.0(3) . . ?
N1 C1 C2 126.5(4) . . ?
N2 C1 N1 122.4(4) . . ?
N2 C1 C2 111.1(4) . . ?
C1 C2 I1 125.3(3) . . ?
C3 C2 I1 128.8(3) . . ?
C3 C2 C1 105.9(3) . . ?
N3 C3 H3 126.7 . . ?
C2 C3 N3 106.7(3) . . ?
C2 C3 H3 126.7 . . ?
O1 C4 N3 119.3(4) . . ?
O1 C4 C5 124.7(4) . . ?
N3 C4 C5 116.0(3) . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C4 C5 C6 112.1(3) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 C5 112.1(3) . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C8 C7 C6 121.4(4) . . ?
C8 C7 C12 117.9(4) . . ?
C12 C7 C6 120.8(4) . . ?
C7 C8 H8 119.1 . . ?
C7 C8 C9 121.9(4) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.1(4) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.0(4) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.6(4) . . ?
C11 C12 H12 119.7 . . ?

_olex2_date_sample_data_collection 2019-08-23
_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 2.216
_oxdiff_exptl_absorpt_empirical_full_min 0.541
