# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
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data_2008314588_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2031635'
loop_
_audit_author_name
_audit_author_address
'jing wu'
;Jiangnan University
China
;
_audit_update_record             
;
2020-09-12 deposited with the CCDC.	2021-04-08 downloaded from the CCDC.
;
_audit_creation_date             2020-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H21 I N2 O2'
_chemical_formula_sum            'C31 H21 I N2 O2'
_chemical_formula_weight         580.40
_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 0.0148 0.0070 '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 0.0969 5.4976 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.3944(5)
_cell_length_b                   10.9292(5)
_cell_length_c                   21.8609(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.850(3)
_cell_angle_gamma                90
_cell_volume                     2453.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8264
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.809
_cell_measurement_theta_min      3.56
_shelx_estimated_absorpt_T_max   0.678
_shelx_estimated_absorpt_T_min   0.603
_exptl_absorpt_coefficient_mu    7.032
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1580 before and 0.0754 after correction. The Ratio of minimum to maximum transmission is 0.6602. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0841
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24560
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.947
_diffrn_reflns_theta_min         3.560
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3077
_reflns_number_total             4517
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         1.935
_refine_diff_density_min         -0.838
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4517
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0585
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+6.8617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1380
_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.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27),
  C29(H29), C30(H30)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 0.94136(5) 0.68472(4) 1.00058(2) 0.0540(2) Uani 1 1 d . . . . .
O1 O 0.4610(4) 0.4039(4) 0.81155(18) 0.0364(10) Uani 1 1 d . . . . .
O2 O 0.2714(4) 0.1021(3) 0.64410(17) 0.0304(9) Uani 1 1 d . . . . .
N1 N 0.5931(4) 0.5051(4) 0.7548(2) 0.0257(11) Uani 1 1 d . . . . .
N2 N 0.2471(4) 0.4287(4) 0.6108(2) 0.0258(11) Uani 1 1 d . . . . .
C1 C 0.3316(5) 0.4699(5) 0.6596(3) 0.0310(14) Uani 1 1 d . . . . .
C2 C 0.3993(5) 0.3913(5) 0.7038(3) 0.0284(13) Uani 1 1 d . . . . .
C3 C 0.3735(5) 0.2659(5) 0.6968(3) 0.0268(13) Uani 1 1 d . . . . .
C4 C 0.4108(5) 0.1547(5) 0.7316(3) 0.0264(13) Uani 1 1 d . . . . .
C5 C 0.4902(5) 0.1260(6) 0.7881(3) 0.0294(13) Uani 1 1 d . . . . .
H5 H 0.535043 0.188244 0.813133 0.035 Uiso 1 1 calc R . . . .
C6 C 0.5010(6) 0.0048(6) 0.8058(3) 0.0388(16) Uani 1 1 d . . . . .
H6 H 0.553708 -0.016570 0.843732 0.047 Uiso 1 1 calc R . . . .
C7 C 0.4357(6) -0.0869(6) 0.7689(3) 0.0368(15) Uani 1 1 d . . . . .
H7 H 0.446014 -0.169631 0.782091 0.044 Uiso 1 1 calc R . . . .
C8 C 0.3567(6) -0.0606(5) 0.7140(3) 0.0324(14) Uani 1 1 d . . . . .
H8 H 0.311258 -0.122814 0.689095 0.039 Uiso 1 1 calc R . . . .
C9 C 0.3472(5) 0.0606(5) 0.6973(3) 0.0273(13) Uani 1 1 d . . . . .
C10 C 0.2882(5) 0.2276(5) 0.6447(3) 0.0268(13) Uani 1 1 d . . . . .
C11 C 0.2250(5) 0.3094(5) 0.6017(2) 0.0252(12) Uani 1 1 d . . . . .
C12 C 0.1303(5) 0.2726(5) 0.5469(2) 0.0281(13) Uani 1 1 d . . . . .
C13 C 0.0286(6) 0.3533(5) 0.5254(3) 0.0309(14) Uani 1 1 d . . . . .
H13 H 0.019773 0.428002 0.546661 0.037 Uiso 1 1 calc R . . . .
C14 C -0.0596(6) 0.3237(5) 0.4729(3) 0.0334(14) Uani 1 1 d . . . . .
H14 H -0.128547 0.378436 0.458360 0.040 Uiso 1 1 calc R . . . .
C15 C -0.0477(6) 0.2156(5) 0.4417(3) 0.0362(16) Uani 1 1 d . . . . .
H15 H -0.107163 0.196021 0.405510 0.043 Uiso 1 1 calc R . . . .
C16 C 0.0527(7) 0.1356(6) 0.4641(3) 0.0428(17) Uani 1 1 d . . . . .
H16 H 0.059969 0.060319 0.443139 0.051 Uiso 1 1 calc R . . . .
C17 C 0.1410(6) 0.1621(5) 0.5152(3) 0.0355(15) Uani 1 1 d . . . . .
H17 H 0.209216 0.106234 0.529268 0.043 Uiso 1 1 calc R . . . .
C18 C 0.3380(6) 0.6057(5) 0.6648(3) 0.0315(14) Uani 1 1 d . . . . .
H18A H 0.394913 0.637874 0.636823 0.047 Uiso 1 1 calc GR . . . .
H18B H 0.372740 0.628668 0.707516 0.047 Uiso 1 1 calc GR . . . .
H18C H 0.250390 0.640027 0.653593 0.047 Uiso 1 1 calc GR . . . .
C19 C 0.6332(5) 0.5358(5) 0.6975(2) 0.0255(13) Uani 1 1 d . . . . .
C20 C 0.6624(6) 0.6571(5) 0.6850(3) 0.0319(14) Uani 1 1 d . . . . .
H20 H 0.656981 0.717830 0.715570 0.038 Uiso 1 1 calc R . . . .
C21 C 0.6984(6) 0.6906(6) 0.6300(3) 0.0393(16) Uani 1 1 d . . . . .
H21 H 0.717003 0.773904 0.622562 0.047 Uiso 1 1 calc R . . . .
C22 C 0.7078(6) 0.6045(7) 0.5856(3) 0.0434(17) Uani 1 1 d . . . . .
H22 H 0.730962 0.628409 0.546942 0.052 Uiso 1 1 calc R . . . .
C23 C 0.6837(6) 0.4826(7) 0.5966(3) 0.0423(17) Uani 1 1 d . . . . .
H23 H 0.691627 0.423179 0.565707 0.051 Uiso 1 1 calc R . . . .
C24 C 0.6480(6) 0.4466(6) 0.6524(3) 0.0321(14) Uani 1 1 d . . . . .
H24 H 0.633704 0.362581 0.660257 0.039 Uiso 1 1 calc R . . . .
C25 C 0.6720(5) 0.5491(5) 0.8111(2) 0.0241(13) Uani 1 1 d . . . . .
C26 C 0.6165(6) 0.6149(5) 0.8546(3) 0.0327(14) Uani 1 1 d . . . . .
H26 H 0.526310 0.634221 0.847144 0.039 Uiso 1 1 calc R . . . .
C27 C 0.6936(6) 0.6524(5) 0.9092(3) 0.0323(14) Uani 1 1 d . . . . .
H27 H 0.656236 0.696109 0.939662 0.039 Uiso 1 1 calc R . . . .
C28 C 0.8234(6) 0.6257(5) 0.9185(3) 0.0308(14) Uani 1 1 d . . . . .
C29 C 0.8809(6) 0.5616(6) 0.8758(3) 0.0331(14) Uani 1 1 d . . . . .
H29 H 0.971537 0.544483 0.883227 0.040 Uiso 1 1 calc R . . . .
C30 C 0.8036(5) 0.5220(5) 0.8214(3) 0.0315(14) Uani 1 1 d . . . . .
H30 H 0.841296 0.476579 0.791625 0.038 Uiso 1 1 calc R . . . .
C31 C 0.4858(6) 0.4345(5) 0.7609(3) 0.0287(14) Uani 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 C28 2.113(5) . ?
O1 C31 1.220(7) . ?
O2 C9 1.378(6) . ?
O2 C10 1.382(7) . ?
N1 C19 1.421(7) . ?
N1 C25 1.452(6) . ?
N1 C31 1.380(7) . ?
N2 C1 1.351(7) . ?
N2 C11 1.334(7) . ?
C1 C2 1.400(8) . ?
C1 C18 1.490(8) . ?
C2 C3 1.400(8) . ?
C2 C31 1.499(7) . ?
C3 C4 1.454(7) . ?
C3 C10 1.397(7) . ?
C4 C5 1.410(7) . ?
C4 C9 1.380(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.376(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.374(8) . ?
C10 C11 1.387(7) . ?
C11 C12 1.484(7) . ?
C12 C13 1.401(8) . ?
C12 C17 1.406(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.394(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(9) . ?
C16 H16 0.9500 . ?
C16 C17 1.363(8) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.396(8) . ?
C19 C24 1.411(8) . ?
C20 H20 0.9500 . ?
C20 C21 1.362(9) . ?
C21 H21 0.9500 . ?
C21 C22 1.367(10) . ?
C22 H22 0.9500 . ?
C22 C23 1.383(10) . ?
C23 H23 0.9500 . ?
C23 C24 1.385(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(8) . ?
C25 C30 1.384(8) . ?
C26 H26 0.9500 . ?
C26 C27 1.394(8) . ?
C27 H27 0.9500 . ?
C27 C28 1.364(8) . ?
C28 C29 1.374(9) . ?
C29 H29 0.9500 . ?
C29 C30 1.398(8) . ?
C30 H30 0.9500 . ?

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
C9 O2 C10 105.3(4) . . ?
C19 N1 C25 117.7(4) . . ?
C31 N1 C19 124.7(4) . . ?
C31 N1 C25 117.6(5) . . ?
C11 N2 C1 121.3(5) . . ?
N2 C1 C2 122.6(5) . . ?
N2 C1 C18 114.1(5) . . ?
C2 C1 C18 123.2(5) . . ?
C1 C2 C3 117.3(5) . . ?
C1 C2 C31 123.8(5) . . ?
C3 C2 C31 118.7(5) . . ?
C2 C3 C4 136.8(5) . . ?
C10 C3 C2 118.0(5) . . ?
C10 C3 C4 105.2(5) . . ?
C5 C4 C3 135.8(5) . . ?
C9 C4 C3 105.8(5) . . ?
C9 C4 C5 118.4(5) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 C4 118.1(6) . . ?
C6 C5 H5 120.9 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.1(6) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.8(6) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 121.9 . . ?
C9 C8 C7 116.2(5) . . ?
C9 C8 H8 121.9 . . ?
O2 C9 C4 112.2(5) . . ?
C8 C9 O2 123.4(5) . . ?
C8 C9 C4 124.5(5) . . ?
O2 C10 C3 111.6(4) . . ?
O2 C10 C11 126.0(5) . . ?
C11 C10 C3 122.4(5) . . ?
N2 C11 C10 118.5(5) . . ?
N2 C11 C12 117.5(5) . . ?
C10 C11 C12 124.0(5) . . ?
C13 C12 C11 118.2(5) . . ?
C13 C12 C17 119.3(5) . . ?
C17 C12 C11 122.5(5) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.7(6) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(6) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 118.9(5) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 119.0 . . ?
C17 C16 C15 121.9(6) . . ?
C17 C16 H16 119.0 . . ?
C12 C17 H17 120.3 . . ?
C16 C17 C12 119.5(6) . . ?
C16 C17 H17 120.3 . . ?
C1 C18 H18A 109.5 . . ?
C1 C18 H18B 109.5 . . ?
C1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 N1 119.9(5) . . ?
C20 C19 C24 118.0(5) . . ?
C24 C19 N1 122.1(5) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.7(6) . . ?
C21 C20 H20 119.2 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.1(6) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.3(6) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.5(6) . . ?
C24 C23 H23 119.8 . . ?
C19 C24 H24 120.3 . . ?
C23 C24 C19 119.4(6) . . ?
C23 C24 H24 120.3 . . ?
C26 C25 N1 120.8(5) . . ?
C30 C25 N1 118.9(5) . . ?
C30 C25 C26 120.3(5) . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.6(6) . . ?
C27 C26 H26 120.2 . . ?
C26 C27 H27 120.3 . . ?
C28 C27 C26 119.3(6) . . ?
C28 C27 H27 120.3 . . ?
C27 C28 I1 119.5(4) . . ?
C27 C28 C29 122.1(5) . . ?
C29 C28 I1 118.4(4) . . ?
C28 C29 H29 120.6 . . ?
C28 C29 C30 118.8(5) . . ?
C30 C29 H29 120.6 . . ?
C25 C30 C29 119.8(6) . . ?
C25 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
O1 C31 N1 121.8(5) . . ?
O1 C31 C2 119.0(5) . . ?
N1 C31 C2 119.1(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
