# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_wu
_database_code_depnum_ccdc_archive 'CCDC 2205149'
loop_
_audit_author_name
_audit_author_address
zm
;SCUT
China
;
_audit_update_record             
;
2022-09-04 deposited with the CCDC.	2023-07-11 downloaded from the CCDC.
;
_audit_creation_date             2020-09-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 I N3'
_chemical_formula_sum            'C19 H18 I N3'
_chemical_formula_weight         415.26
_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 0.0033 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'
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        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.6151(11)
_cell_length_b                   10.3343(4)
_cell_length_c                   18.5855(9)
_cell_angle_alpha                90
_cell_angle_beta                 125.115(3)
_cell_angle_gamma                90
_cell_volume                     3396.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.373
_cell_measurement_theta_min      2.283
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.765
_exptl_absorpt_coefficient_mu    1.889
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0980 before and 0.0479 after correction. The Ratio of minimum to maximum transmission is 0.7719. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19018
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.430
_diffrn_reflns_theta_min         2.283
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3027
_reflns_number_total             3460
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.610
_refine_diff_density_min         -1.275
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3460
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.022
_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)+(0.0160P)²+15.5832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0700
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N3-H3
 0.87 with sigma of 0.02
 H6-H3
 2.2 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C10(H10), C13(H13), C11(H11), C3(H3A), C4(H4), C5(H5)
3.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_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 0.63255(2) 0.69128(2) 0.40326(2) 0.04631(10) Uani 1 1 d . . . . .
N2 N 0.72137(13) 0.2279(2) 0.62637(15) 0.0245(5) Uani 1 1 d . . . . .
N1 N 0.61398(12) 0.3427(2) 0.51414(14) 0.0205(5) Uani 1 1 d . . . . .
N3 N 0.60244(13) 0.1786(2) 0.59188(16) 0.0249(5) Uani 1 1 d D . . . .
C15 C 0.64960(15) 0.2493(3) 0.58044(17) 0.0214(5) Uani 1 1 d . . . . .
C14 C 0.76598(15) 0.2989(3) 0.60897(18) 0.0231(6) Uani 1 1 d . . . . .
C9 C 0.73743(15) 0.4034(3) 0.54960(18) 0.0224(6) Uani 1 1 d . . . . .
C8 C 0.65754(16) 0.4313(3) 0.50254(18) 0.0225(6) Uani 1 1 d . . . . .
C1 C 0.60891(17) 0.5215(3) 0.44239(19) 0.0272(6) Uani 1 1 d . . . . .
C7 C 0.53708(15) 0.3763(3) 0.45687(17) 0.0234(6) Uani 1 1 d . . . . .
C2 C 0.53367(16) 0.4891(3) 0.41194(18) 0.0262(6) Uani 1 1 d . . . . .
C12 C 0.88936(17) 0.3321(3) 0.6395(2) 0.0335(7) Uani 1 1 d . . . . .
H12 H 0.941130 0.308444 0.670298 0.040 Uiso 1 1 calc R . . . .
C10 C 0.78646(17) 0.4699(3) 0.5356(2) 0.0304(7) Uani 1 1 d . . . . .
H10 H 0.767774 0.539886 0.495107 0.036 Uiso 1 1 calc R . . . .
C6 C 0.47081(16) 0.3199(3) 0.4383(2) 0.0288(6) Uani 1 1 d . . . . .
C13 C 0.84214(16) 0.2649(3) 0.65373(19) 0.0295(6) Uani 1 1 d . . . . .
H13 H 0.861583 0.194902 0.694252 0.035 Uiso 1 1 calc R . . . .
C11 C 0.86114(17) 0.4345(3) 0.5800(2) 0.0349(7) Uani 1 1 d . . . . .
H11 H 0.893728 0.480253 0.570139 0.042 Uiso 1 1 calc R . . . .
C16 C 0.62842(16) 0.0782(3) 0.66108(19) 0.0267(6) Uani 1 1 d . . . . .
C3 C 0.46361(18) 0.5464(3) 0.34967(19) 0.0336(7) Uani 1 1 d . . . . .
H3A H 0.460939 0.622020 0.318938 0.040 Uiso 1 1 calc R . . . .
C18 C 0.66577(19) -0.0329(3) 0.6453(2) 0.0363(7) Uani 1 1 d . . . . .
H18A H 0.630732 -0.066147 0.585374 0.054 Uiso 1 1 calc GR . . . .
H18B H 0.678670 -0.102362 0.687650 0.054 Uiso 1 1 calc GR . . . .
H18C H 0.711893 -0.001666 0.652601 0.054 Uiso 1 1 calc GR . . . .
C4 C 0.39917(17) 0.4919(3) 0.3338(2) 0.0367(8) Uani 1 1 d . . . . .
H4 H 0.351548 0.530883 0.292453 0.044 Uiso 1 1 calc R . . . .
C5 C 0.40267(17) 0.3796(3) 0.3777(2) 0.0335(7) Uani 1 1 d . . . . .
H5 H 0.357229 0.343344 0.365673 0.040 Uiso 1 1 calc R . . . .
C17 C 0.55613(18) 0.0299(3) 0.6489(2) 0.0392(8) Uani 1 1 d . . . . .
H17A H 0.530989 0.102260 0.656390 0.059 Uiso 1 1 calc GR . . . .
H17B H 0.568865 -0.036973 0.692783 0.059 Uiso 1 1 calc GR . . . .
H17C H 0.522188 -0.006463 0.589761 0.059 Uiso 1 1 calc GR . . . .
C19 C 0.68197(19) 0.1357(3) 0.7529(2) 0.0377(7) Uani 1 1 d . . . . .
H19A H 0.727484 0.168355 0.759357 0.057 Uiso 1 1 calc GR . . . .
H19B H 0.696162 0.068639 0.797158 0.057 Uiso 1 1 calc GR . . . .
H19C H 0.656628 0.206860 0.761069 0.057 Uiso 1 1 calc GR . . . .
H6 H 0.4674(16) 0.243(4) 0.4599(18) 0.036(9) Uiso 1 1 d D . . . .
H3 H 0.5706(14) 0.227(3) 0.5918(19) 0.047(11) Uiso 1 1 d 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 C1 2.073(3) . ?
N2 C15 1.289(3) . ?
N2 C14 1.390(4) . ?
N1 C15 1.397(3) . ?
N1 C8 1.416(3) . ?
N1 C7 1.408(3) . ?
N3 C15 1.366(4) . ?
N3 C16 1.488(3) . ?
N3 H3 0.849(18) . ?
C14 C9 1.407(4) . ?
C14 C13 1.397(4) . ?
C9 C8 1.447(4) . ?
C9 C10 1.407(4) . ?
C8 C1 1.368(4) . ?
C1 C2 1.421(4) . ?
C7 C2 1.410(4) . ?
C7 C6 1.393(4) . ?
C2 C3 1.403(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(4) . ?
C12 C11 1.393(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.374(4) . ?
C6 C5 1.382(4) . ?
C6 H6 0.91(4) . ?
C13 H13 0.9500 . ?
C11 H11 0.9500 . ?
C16 C18 1.527(4) . ?
C16 C17 1.528(4) . ?
C16 C19 1.527(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.368(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C4 H4 0.9500 . ?
C4 C5 1.396(5) . ?
C5 H5 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C15 N2 C14 119.2(2) . . ?
C15 N1 C8 120.3(2) . . ?
C15 N1 C7 130.5(2) . . ?
C7 N1 C8 108.9(2) . . ?
C15 N3 C16 124.2(2) . . ?
C15 N3 H3 111(3) . . ?
C16 N3 H3 108(2) . . ?
N2 C15 N1 123.0(2) . . ?
N2 C15 N3 121.8(2) . . ?
N3 C15 N1 115.1(2) . . ?
N2 C14 C9 122.5(2) . . ?
N2 C14 C13 117.8(3) . . ?
C13 C14 C9 119.7(3) . . ?
C14 C9 C8 117.4(2) . . ?
C10 C9 C14 118.8(3) . . ?
C10 C9 C8 123.7(3) . . ?
N1 C8 C9 116.5(2) . . ?
C1 C8 N1 107.4(2) . . ?
C1 C8 C9 136.0(3) . . ?
C8 C1 I1 129.4(2) . . ?
C8 C1 C2 109.3(2) . . ?
C2 C1 I1 121.1(2) . . ?
N1 C7 C2 106.8(2) . . ?
C6 C7 N1 133.0(3) . . ?
C6 C7 C2 120.2(3) . . ?
C7 C2 C1 107.5(2) . . ?
C3 C2 C1 132.4(3) . . ?
C3 C2 C7 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.7 . . ?
C7 C6 H6 126.0(19) . . ?
C5 C6 C7 118.5(3) . . ?
C5 C6 H6 115.3(18) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13 119.8 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
N3 C16 C18 109.7(2) . . ?
N3 C16 C17 104.7(2) . . ?
N3 C16 C19 111.2(2) . . ?
C18 C16 C17 109.6(3) . . ?
C18 C16 C19 111.3(3) . . ?
C19 C16 C17 110.2(3) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 C2 119.1(3) . . ?
C4 C3 H3A 120.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
