# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 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_wjl-1
_database_code_depnum_ccdc_archive 'CCDC 2237111'
loop_
_audit_author_name
_audit_author_address
wujianglong
;Ningxia University
China
;
_audit_update_record             
;
2023-01-19 deposited with the CCDC.	2023-01-27 downloaded from the CCDC.
;
_audit_creation_date             2022-07-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 I N O'
_chemical_formula_sum            'C15 H10 I N O'
_chemical_formula_weight         347.14
_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'
O O 0.0106 0.0060 '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                   13.0551(6)
_cell_length_b                   7.4021(3)
_cell_length_c                   13.9932(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.381(2)
_cell_angle_gamma                90
_cell_volume                     1325.65(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7995
_cell_measurement_temperature    300.0
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.97
_shelx_estimated_absorpt_T_max   0.778
_shelx_estimated_absorpt_T_min   0.658
_exptl_absorpt_coefficient_mu    2.402
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1627 before and 0.0371 after correction.
The Ratio of minimum to maximum transmission is 0.8340.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12688
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.578
_diffrn_reflns_theta_min         1.591
_diffrn_ambient_temperature      300.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2437
_reflns_number_total             2735
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.922
_refine_diff_density_min         -1.017
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2735
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      0.997
_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)+(0.0601P)²+1.2726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0982
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14)
2.b X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_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
C C 0.7561(2) 0.4478(3) 0.4793(2) 0.0403(6) Uani 1 1 d . . . . .
C2 C 0.8583(2) 0.4484(4) 0.5451(2) 0.0403(6) Uani 1 1 d . . . . .
C3 C 0.9239(3) 0.5892(4) 0.5831(2) 0.0493(7) Uani 1 1 d . . . . .
H3 H 0.905240 0.708803 0.568721 0.059 Uiso 1 1 calc R U . . .
C4 C 1.0179(3) 0.5457(5) 0.6432(3) 0.0573(9) Uani 1 1 d . . . . .
H4 H 1.063088 0.638282 0.669192 0.069 Uiso 1 1 calc R U . . .
C5 C 1.0469(3) 0.3688(6) 0.6659(3) 0.0628(9) Uani 1 1 d . . . . .
H5 H 1.111052 0.344458 0.706107 0.075 Uiso 1 1 calc R U . . .
C6 C 0.9813(3) 0.2278(5) 0.6292(3) 0.0558(8) Uani 1 1 d . . . . .
H6 H 1.000026 0.108454 0.644509 0.067 Uiso 1 1 calc R U . . .
C7 C 0.8867(2) 0.2702(4) 0.5689(2) 0.0433(6) Uani 1 1 d . . . . .
C8 C 0.8017(3) 0.1507(4) 0.5226(2) 0.0472(7) Uani 1 1 d . . . . .
O9 O 0.7934(2) -0.0120(3) 0.5290(2) 0.0683(8) Uani 1 1 d . . . . .
C10 C 0.6276(2) 0.2004(4) 0.4191(2) 0.0434(6) Uani 1 1 d . . . . .
C11 C 0.5395(3) 0.2347(5) 0.4585(3) 0.0541(8) Uani 1 1 d . . . . .
H11 H 0.545611 0.302251 0.515358 0.065 Uiso 1 1 calc R U . . .
C12 C 0.4428(3) 0.1683(5) 0.4131(3) 0.0628(9) Uani 1 1 d . . . . .
H12 H 0.383807 0.193750 0.438666 0.075 Uiso 1 1 calc R U . . .
C13 C 0.4341(3) 0.0651(5) 0.3304(3) 0.0626(10) Uani 1 1 d . . . . .
H13 H 0.369383 0.018121 0.301230 0.075 Uiso 1 1 calc R U . . .
C14 C 0.5200(3) 0.0304(5) 0.2901(3) 0.0566(8) Uani 1 1 d . . . . .
H14 H 0.513529 -0.040346 0.234336 0.068 Uiso 1 1 calc R U . . .
C15 C 0.6169(2) 0.1019(4) 0.3334(2) 0.0448(7) Uani 1 1 d . . . . .
I1 I 0.74211(2) 0.06423(4) 0.26254(2) 0.06537(14) Uani 1 1 d . . . . .
N1 N 0.7264(2) 0.2632(3) 0.46906(19) 0.0438(6) Uani 1 1 d . . . . .
C1 C 0.7022(3) 0.5849(4) 0.4353(3) 0.0530(8) Uani 1 1 d . . . . .
H1A H 0.638627 0.564561 0.393172 0.064 Uiso 1 1 calc R U . . .
H1B H 0.727601 0.701961 0.446244 0.064 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
C C2 1.463(4) . ?
C N1 1.420(3) . ?
C C1 1.317(4) . ?
C2 C3 1.387(4) . ?
C2 C7 1.393(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.387(4) . ?
C7 C8 1.467(4) . ?
C8 O9 1.214(4) . ?
C8 N1 1.389(4) . ?
C10 C11 1.393(5) . ?
C10 C15 1.387(4) . ?
C10 N1 1.418(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.395(5) . ?
C15 I1 2.091(3) . ?
C1 H1A 0.9300 . ?
C1 H1B 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
N1 C C2 105.3(2) . . ?
C1 C C2 129.0(3) . . ?
C1 C N1 125.7(3) . . ?
C3 C2 C 131.4(3) . . ?
C3 C2 C7 120.3(3) . . ?
C7 C2 C 108.3(2) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 C2 117.8(3) . . ?
C4 C3 H3 121.1 . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 122.0(3) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 121.1 . . ?
C7 C6 C5 117.8(3) . . ?
C7 C6 H6 121.1 . . ?
C2 C7 C8 108.8(3) . . ?
C6 C7 C2 121.6(3) . . ?
C6 C7 C8 129.6(3) . . ?
O9 C8 C7 129.5(3) . . ?
O9 C8 N1 124.8(3) . . ?
N1 C8 C7 105.7(2) . . ?
C11 C10 N1 119.2(3) . . ?
C15 C10 C11 119.2(3) . . ?
C15 C10 N1 121.6(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
C10 C15 C14 120.2(3) . . ?
C10 C15 I1 121.7(2) . . ?
C14 C15 I1 118.0(3) . . ?
C8 N1 C 111.8(3) . . ?
C8 N1 C10 123.2(2) . . ?
C10 N1 C 124.7(2) . . ?
C C1 H1A 120.0 . . ?
C C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?

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
C C2 C3 C4 -179.0(3) . . . . ?
C C2 C7 C6 178.8(3) . . . . ?
C C2 C7 C8 -2.5(4) . . . . ?
C2 C N1 C8 -0.2(4) . . . . ?
C2 C N1 C10 173.4(3) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C2 C7 C8 O9 -176.0(4) . . . . ?
C2 C7 C8 N1 2.3(4) . . . . ?
C3 C2 C7 C6 -1.3(5) . . . . ?
C3 C2 C7 C8 177.4(3) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C4 C5 C6 C7 0.5(6) . . . . ?
C5 C6 C7 C2 0.4(5) . . . . ?
C5 C6 C7 C8 -178.0(3) . . . . ?
C6 C7 C8 O9 2.6(6) . . . . ?
C6 C7 C8 N1 -179.1(3) . . . . ?
C7 C2 C3 C4 1.2(5) . . . . ?
C7 C8 N1 C -1.3(4) . . . . ?
C7 C8 N1 C10 -175.0(3) . . . . ?
O9 C8 N1 C 177.2(3) . . . . ?
O9 C8 N1 C10 3.4(5) . . . . ?
C10 C11 C12 C13 1.5(6) . . . . ?
C11 C10 C15 C14 -3.3(5) . . . . ?
C11 C10 C15 I1 174.3(2) . . . . ?
C11 C10 N1 C -68.6(4) . . . . ?
C11 C10 N1 C8 104.3(4) . . . . ?
C11 C12 C13 C14 -1.8(6) . . . . ?
C12 C13 C14 C15 -0.4(6) . . . . ?
C13 C14 C15 C10 3.0(5) . . . . ?
C13 C14 C15 I1 -174.7(3) . . . . ?
C15 C10 C11 C12 1.1(5) . . . . ?
C15 C10 N1 C 113.0(4) . . . . ?
C15 C10 N1 C8 -74.1(4) . . . . ?
N1 C C2 C3 -178.2(3) . . . . ?
N1 C C2 C7 1.6(3) . . . . ?
N1 C10 C11 C12 -177.4(3) . . . . ?
N1 C10 C15 C14 175.1(3) . . . . ?
N1 C10 C15 I1 -7.3(4) . . . . ?
C1 C C2 C3 3.6(6) . . . . ?
C1 C C2 C7 -176.5(4) . . . . ?
C1 C N1 C8 178.0(3) . . . . ?
C1 C N1 C10 -8.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
