# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_534_0m
_database_code_depnum_ccdc_archive 'CCDC 2120040'
loop_
_audit_author_name
_audit_author_address
'Yan-Ping Zhu'
;Yantai University
China
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 I N4 O2'
_chemical_formula_weight         434.23

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3683(16)
_cell_length_b                   9.4908(16)
_cell_length_c                   10.5784(18)
_cell_angle_alpha                87.911(2)
_cell_angle_beta                 71.723(2)
_cell_angle_gamma                70.747(2)
_cell_volume                     840.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2959
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.53


_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.922
_shelx_estimated_absorpt_T_min   0.724
_shelx_estimated_absorpt_T_max   0.761
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5194
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.279
_diffrn_reflns_theta_max         27.612
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3777
_reflns_number_gt                3403
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3777
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.09778(2) 0.13487(2) 0.33792(2) 0.04144(9) Uani 1 1 d . . . . .
O1 O 0.7657(3) -0.0919(2) 0.2269(2) 0.0510(6) Uani 1 1 d . . . . .
O2 O 0.8018(3) 0.1202(3) 0.2723(2) 0.0509(6) Uani 1 1 d . . . . .
O3 O 0.7737(3) 0.4903(3) 0.7976(3) 0.0679(7) Uani 1 1 d . . . . .
O4 O 0.5188(3) 0.6409(2) 0.8713(2) 0.0477(5) Uani 1 1 d . . . . .
N1 N 0.4463(3) 0.0543(3) 0.3107(2) 0.0355(5) Uani 1 1 d . . . . .
N2 N 0.4597(3) 0.2130(2) 0.4558(2) 0.0296(4) Uani 1 1 d . . . . .
C1 C 0.9492(6) -0.2713(6) 0.0489(4) 0.0873(15) Uani 1 1 d . . . . .
H1A H 0.901631 -0.226524 -0.017471 0.131 Uiso 1 1 calc R U . . .
H1B H 0.897155 -0.339092 0.094722 0.131 Uiso 1 1 calc R U . . .
H1C H 1.060494 -0.325195 0.006575 0.131 Uiso 1 1 calc R U . . .
C2 C 0.9311(4) -0.1536(4) 0.1453(4) 0.0673(12) Uani 1 1 d . . . . .
H2A H 0.996890 -0.195304 0.201476 0.081 Uiso 1 1 calc R U . . .
H2B H 0.965940 -0.075176 0.098054 0.081 Uiso 1 1 calc R U . . .
C3 C 0.7175(3) 0.0447(3) 0.2845(3) 0.0356(6) Uani 1 1 d . . . . .
C4 C 0.5435(3) 0.0971(3) 0.3573(3) 0.0319(5) Uani 1 1 d . . . . .
C5 C 0.2973(3) 0.1449(3) 0.3780(3) 0.0329(6) Uani 1 1 d . . . . .
C6 C 0.2988(3) 0.2464(3) 0.4688(3) 0.0319(5) Uani 1 1 d . . . . .
C7 C 0.1788(3) 0.3662(3) 0.5579(3) 0.0388(6) Uani 1 1 d . . . . .
H7 H 0.071976 0.387632 0.565663 0.047 Uiso 1 1 calc R U . . .
C8 C 0.2219(3) 0.4488(3) 0.6314(3) 0.0396(6) Uani 1 1 d . . . . .
H8 H 0.144882 0.531384 0.685735 0.048 Uiso 1 1 calc R U . . .
C9 C 0.3861(3) 0.4098(3) 0.6264(3) 0.0326(5) Uani 1 1 d . . . . .
C10 C 0.5051(3) 0.2866(3) 0.5432(3) 0.0301(5) Uani 1 1 d . . . . .
C11 C 0.6596(3) 0.2377(3) 0.5505(3) 0.0351(6) Uani 1 1 d . . . . .
H11 H 0.735637 0.152052 0.500012 0.042 Uiso 1 1 calc R U . . .
C12 C 0.6990(4) 0.3170(3) 0.6331(3) 0.0382(6) Uani 1 1 d . . . . .
H12 H 0.802416 0.285005 0.637239 0.046 Uiso 1 1 calc R U . . .
C13 C 0.5853(4) 0.4451(3) 0.7109(3) 0.0360(6) Uani 1 1 d . . . . .
C14 C 0.4304(4) 0.4895(3) 0.7090(3) 0.0362(6) Uani 1 1 d . . . . .
H14 H 0.354202 0.572930 0.762705 0.043 Uiso 1 1 calc R U . . .
C15 C 0.6386(4) 0.5260(3) 0.7969(3) 0.0415(7) Uani 1 1 d . . . . .
C16 C 0.5570(5) 0.7227(4) 0.9631(3) 0.0513(8) Uani 1 1 d . . . . .
H16A H 0.637463 0.765148 0.913850 0.062 Uiso 1 1 calc R U . . .
H16B H 0.598194 0.655824 1.024636 0.062 Uiso 1 1 calc R U . . .
C17 C 0.4080(5) 0.8435(4) 1.0375(4) 0.0644(10) Uani 1 1 d . . . . .
H17A H 0.372535 0.912993 0.976442 0.097 Uiso 1 1 calc R U . . .
H17B H 0.428011 0.894828 1.103156 0.097 Uiso 1 1 calc R U . . .
H17C H 0.327013 0.800790 1.081031 0.097 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 C5 2.074(3) . ?
O1 C3 1.325(3) . ?
O1 C2 1.445(4) . ?
O2 C3 1.207(4) . ?
O3 C15 1.199(4) . ?
O4 C15 1.331(4) . ?
O4 C16 1.459(4) . ?
N1 C4 1.332(3) . ?
N1 C5 1.351(4) . ?
N2 C4 1.384(3) . ?
N2 C6 1.397(3) . ?
N2 C10 1.419(3) . ?
C1 C2 1.472(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.485(4) . ?
C5 C6 1.391(4) . ?
C6 C7 1.420(4) . ?
C7 C8 1.354(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.442(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.409(4) . ?
C9 C14 1.411(4) . ?
C10 C11 1.393(4) . ?
C11 C12 1.378(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.400(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(4) . ?
C13 C15 1.502(4) . ?
C14 H14 0.9300 . ?
C16 C17 1.485(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C3 O1 C2 117.0(3) . . ?
C15 O4 C16 116.2(3) . . ?
C4 N1 C5 105.7(2) . . ?
C4 N2 C6 106.1(2) . . ?
C4 N2 C10 133.3(2) . . ?
C6 N2 C10 120.3(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 109.4(4) . . ?
O1 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
O1 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
O2 C3 O1 124.5(3) . . ?
O2 C3 C4 124.4(3) . . ?
O1 C3 C4 111.0(2) . . ?
N1 C4 N2 111.7(2) . . ?
N1 C4 C3 119.8(2) . . ?
N2 C4 C3 127.0(2) . . ?
N1 C5 C6 111.6(2) . . ?
N1 C5 I1 122.2(2) . . ?
C6 C5 I1 126.2(2) . . ?
C5 C6 N2 104.9(2) . . ?
C5 C6 C7 134.0(3) . . ?
N2 C6 C7 121.1(2) . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C14 118.3(3) . . ?
C10 C9 C8 120.7(3) . . ?
C14 C9 C8 120.9(3) . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 N2 122.0(2) . . ?
C9 C10 N2 117.4(2) . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.7(3) . . ?
C14 C13 C15 122.8(3) . . ?
C12 C13 C15 117.4(3) . . ?
C13 C14 C9 120.7(3) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
O3 C15 O4 124.4(3) . . ?
O3 C15 C13 123.5(3) . . ?
O4 C15 C13 112.0(3) . . ?
O4 C16 C17 107.7(3) . . ?
O4 C16 H16A 110.2 . . ?
C17 C16 H16A 110.2 . . ?
O4 C16 H16B 110.2 . . ?
C17 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C3 O1 C2 C1 -157.1(3) . . . . ?
C2 O1 C3 O2 0.7(5) . . . . ?
C2 O1 C3 C4 176.2(3) . . . . ?
C5 N1 C4 N2 1.0(3) . . . . ?
C5 N1 C4 C3 -166.2(2) . . . . ?
C6 N2 C4 N1 -1.3(3) . . . . ?
C10 N2 C4 N1 173.1(3) . . . . ?
C6 N2 C4 C3 164.7(3) . . . . ?
C10 N2 C4 C3 -20.8(5) . . . . ?
O2 C3 C4 N1 142.3(3) . . . . ?
O1 C3 C4 N1 -33.3(4) . . . . ?
O2 C3 C4 N2 -22.7(5) . . . . ?
O1 C3 C4 N2 161.7(3) . . . . ?
C4 N1 C5 C6 -0.2(3) . . . . ?
C4 N1 C5 I1 176.77(19) . . . . ?
N1 C5 C6 N2 -0.6(3) . . . . ?
I1 C5 C6 N2 -177.42(18) . . . . ?
N1 C5 C6 C7 177.1(3) . . . . ?
I1 C5 C6 C7 0.3(5) . . . . ?
C4 N2 C6 C5 1.1(3) . . . . ?
C10 N2 C6 C5 -174.2(2) . . . . ?
C4 N2 C6 C7 -177.0(2) . . . . ?
C10 N2 C6 C7 7.7(4) . . . . ?
C5 C6 C7 C8 -177.6(3) . . . . ?
N2 C6 C7 C8 -0.2(4) . . . . ?
C6 C7 C8 C9 -4.1(4) . . . . ?
C7 C8 C9 C10 1.1(4) . . . . ?
C7 C8 C9 C14 -176.0(3) . . . . ?
C14 C9 C10 C11 5.1(4) . . . . ?
C8 C9 C10 C11 -171.9(3) . . . . ?
C14 C9 C10 N2 -176.7(2) . . . . ?
C8 C9 C10 N2 6.2(4) . . . . ?
C4 N2 C10 C11 -6.2(4) . . . . ?
C6 N2 C10 C11 167.7(2) . . . . ?
C4 N2 C10 C9 175.7(3) . . . . ?
C6 N2 C10 C9 -10.5(3) . . . . ?
C9 C10 C11 C12 -4.6(4) . . . . ?
N2 C10 C11 C12 177.3(2) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C11 C12 C13 C14 2.5(4) . . . . ?
C11 C12 C13 C15 -179.3(3) . . . . ?
C12 C13 C14 C9 -1.9(4) . . . . ?
C15 C13 C14 C9 -180.0(3) . . . . ?
C10 C9 C14 C13 -1.9(4) . . . . ?
C8 C9 C14 C13 175.2(3) . . . . ?
C16 O4 C15 O3 -2.8(5) . . . . ?
C16 O4 C15 C13 177.3(3) . . . . ?
C14 C13 C15 O3 -178.5(3) . . . . ?
C12 C13 C15 O3 3.4(5) . . . . ?
C14 C13 C15 O4 1.5(4) . . . . ?
C12 C13 C15 O4 -176.6(3) . . . . ?
C15 O4 C16 C17 -179.1(3) . . . . ?

_refine_diff_density_max         1.099
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.088

