# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_202008133
_database_code_depnum_ccdc_archive 'CCDC 2046047'
loop_
_audit_author_name
_audit_author_address
'Dong Li'
; Hubei University of Technology
China
;
_audit_update_record             
;
2020-11-24 deposited with the CCDC.	2021-03-17 downloaded from the CCDC.
;
_audit_creation_date             2020-08-14
_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         'C14 H12 I N O'
_chemical_formula_sum            'C14 H12 I N O'
_chemical_formula_weight         337.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15N2O1S1
_chemical_oxdiff_usercomment     r
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.8944(4)
_cell_length_b                   8.9694(2)
_cell_length_c                   20.9762(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2614.14(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1734
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8460
_cell_measurement_theta_min      3.8320
_shelx_estimated_absorpt_T_max   0.251
_shelx_estimated_absorpt_T_min   0.140
_exptl_absorpt_coefficient_mu    19.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.713
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6023
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.065
_diffrn_reflns_theta_max         67.065
_diffrn_reflns_theta_min         4.215
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  -7.00   1.00    3.50    --  -33.50  77.00-180.00   26
  2  ω      0.00  36.00   1.00    3.50    --  -33.50  77.00-180.00   36
  3  ω    -18.00   8.00   1.00    3.50    --   36.47 -57.00-180.00   26
  4  ω     31.00  57.00   1.00    3.50    --   36.47 -77.00-180.00   26
  5  ω     18.00  79.00   1.00    3.50    --   36.47  37.00 -30.00   61
  6  ω     35.00  74.00   1.00    3.50    --   36.47 -99.00 120.00   39
  7  ω    -32.00  11.00   1.00    3.50    --   36.47 -77.00-180.00   43
  8  ω     23.00  54.00   1.00    3.50    --   36.47 -57.00-180.00   31
  9  ω    117.00 149.00   1.00   10.00    --  108.00 111.00-150.00   32
 10  ω     94.00 119.00   1.00   10.00    --  108.00 -30.00 -90.00   25
 11  ω    141.00 178.00   1.00   10.00    --  108.00  30.00  30.00   37
 12  ω     85.00 117.00   1.00   10.00    --  108.00  30.00  30.00   32
 13  ω     38.00  69.00   1.00   10.00    --  108.00 -30.00 -90.00   31
 14  ω     75.00 111.00   1.00   10.00    --  108.00-111.00 120.00   36
 15  ω    129.00 176.00   1.00   10.00    --  108.00  61.00   0.00   47
 16  ω     40.00 127.00   1.00   10.00    --  108.00 -77.00-120.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1068951000
_diffrn_orient_matrix_UB_12      0.0450011000
_diffrn_orient_matrix_UB_13      0.0020297000
_diffrn_orient_matrix_UB_21      0.0290104000
_diffrn_orient_matrix_UB_22      0.1657521000
_diffrn_orient_matrix_UB_23      -0.0027685000
_diffrn_orient_matrix_UB_31      -0.0040265000
_diffrn_orient_matrix_UB_32      -0.0050018000
_diffrn_orient_matrix_UB_33      -0.0733735000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1761
_reflns_number_total             2327
_reflns_odcompleteness_completeness 99.93
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.903
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.028
_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)+(0.0695P)²+1.2235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1311
_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:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.25231(3) 1.02215(5) 0.28987(2) 0.0605(2) Uani 1 1 d . . . . .
O1 O 0.6774(3) 0.5848(5) 0.49732(19) 0.0632(11) Uani 1 1 d . . . . .
N1 N 0.5692(3) 0.6209(4) 0.4180(2) 0.0412(9) Uani 1 1 d . . . . .
C1 C 0.6263(4) 0.6698(6) 0.4679(2) 0.0474(12) Uani 1 1 d . . . . .
C2 C 0.6223(5) 0.8341(7) 0.4833(3) 0.0587(15) Uani 1 1 d . . . . .
H2A H 0.6161 0.8902 0.4445 0.088 Uiso 1 1 calc GR . . . .
H2B H 0.6803 0.8630 0.5049 0.088 Uiso 1 1 calc GR . . . .
H2C H 0.5679 0.8537 0.5103 0.088 Uiso 1 1 calc GR . . . .
C3 C 0.4972(4) 0.7144(5) 0.3894(2) 0.0375(10) Uani 1 1 d . . . . .
C4 C 0.4171(4) 0.7575(6) 0.4236(2) 0.0461(12) Uani 1 1 d . . . . .
H4 H 0.4097 0.7263 0.4656 0.055 Uiso 1 1 calc R . . . .
C5 C 0.3479(4) 0.8469(6) 0.3958(3) 0.0458(12) Uani 1 1 d . . . . .
H5 H 0.2948 0.8781 0.4192 0.055 Uiso 1 1 calc R . . . .
C6 C 0.3580(3) 0.8897(5) 0.3328(2) 0.0365(10) Uani 1 1 d . . . . .
C7 C 0.4375(4) 0.8453(5) 0.2978(2) 0.0418(11) Uani 1 1 d . . . . .
H7 H 0.4442 0.8746 0.2555 0.050 Uiso 1 1 calc R . . . .
C8 C 0.5074(4) 0.7564(5) 0.3266(2) 0.0390(10) Uani 1 1 d . . . . .
H8 H 0.5609 0.7254 0.3034 0.047 Uiso 1 1 calc R . . . .
C9 C 0.5751(4) 0.4697(5) 0.3972(2) 0.0384(11) Uani 1 1 d . . . . .
C10 C 0.4915(4) 0.3898(6) 0.3866(3) 0.0497(13) Uani 1 1 d . . . . .
H10 H 0.4317 0.4333 0.3937 0.060 Uiso 1 1 calc R . . . .
C11 C 0.4981(6) 0.2427(7) 0.3652(3) 0.0638(17) Uani 1 1 d . . . . .
H11 H 0.4421 0.1888 0.3577 0.077 Uiso 1 1 calc R . . . .
C12 C 0.5860(5) 0.1761(6) 0.3550(3) 0.0654(18) Uani 1 1 d . . . . .
H12 H 0.5896 0.0773 0.3417 0.079 Uiso 1 1 calc R . . . .
C13 C 0.6674(5) 0.2572(6) 0.3646(3) 0.0637(17) Uani 1 1 d . . . . .
H13 H 0.7269 0.2138 0.3567 0.076 Uiso 1 1 calc R . . . .
C14 C 0.6634(4) 0.4025(6) 0.3858(3) 0.0523(14) Uani 1 1 d . . . . .
H14 H 0.7200 0.4556 0.3925 0.063 Uiso 1 1 calc R . . . .


_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 C6 2.093(5) . ?
O1 C1 1.211(7) . ?
N1 C1 1.384(7) . ?
N1 C3 1.437(6) . ?
N1 C9 1.427(6) . ?
C1 C2 1.510(8) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.379(7) . ?
C3 C8 1.378(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(7) . ?
C6 C7 1.385(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.394(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(7) . ?
C9 C14 1.388(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.396(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.360(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(8) . ?
C14 H14 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 C3 122.0(4) . . ?
C1 N1 C9 120.0(4) . . ?
C9 N1 C3 117.8(4) . . ?
O1 C1 N1 121.4(5) . . ?
O1 C1 C2 121.8(5) . . ?
N1 C1 C2 116.8(5) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 N1 120.5(5) . . ?
C8 C3 N1 119.2(5) . . ?
C8 C3 C4 120.3(5) . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.3(5) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.6(5) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 I1 119.8(4) . . ?
C5 C6 C7 120.6(5) . . ?
C7 C6 I1 119.6(4) . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.4(5) . . ?
C8 C7 H7 120.3 . . ?
C3 C8 C7 119.9(5) . . ?
C3 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 N1 119.6(5) . . ?
C10 C9 C14 119.3(5) . . ?
C14 C9 N1 121.1(5) . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119.1(6) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.3(6) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.8(5) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.4(6) . . ?
C14 C13 H13 119.3 . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.1(6) . . ?
C13 C14 H14 119.9 . . ?

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
I1 C6 C7 C8 -179.6(4) . . . . ?
N1 C3 C4 C5 -179.7(5) . . . . ?
N1 C3 C8 C7 179.1(4) . . . . ?
N1 C9 C10 C11 179.0(5) . . . . ?
N1 C9 C14 C13 -178.9(5) . . . . ?
C1 N1 C3 C4 -66.7(7) . . . . ?
C1 N1 C3 C8 115.5(6) . . . . ?
C1 N1 C9 C10 133.6(5) . . . . ?
C1 N1 C9 C14 -47.9(7) . . . . ?
C3 N1 C1 O1 169.9(5) . . . . ?
C3 N1 C1 C2 -10.7(7) . . . . ?
C3 N1 C9 C10 -41.2(7) . . . . ?
C3 N1 C9 C14 137.3(5) . . . . ?
C3 C4 C5 C6 1.7(8) . . . . ?
C4 C3 C8 C7 1.3(7) . . . . ?
C4 C5 C6 I1 179.0(4) . . . . ?
C4 C5 C6 C7 -0.9(7) . . . . ?
C5 C6 C7 C8 0.2(7) . . . . ?
C6 C7 C8 C3 -0.4(7) . . . . ?
C8 C3 C4 C5 -2.0(8) . . . . ?
C9 N1 C1 O1 -4.7(8) . . . . ?
C9 N1 C1 C2 174.8(5) . . . . ?
C9 N1 C3 C4 108.0(5) . . . . ?
C9 N1 C3 C8 -69.8(6) . . . . ?
C9 C10 C11 C12 0.5(9) . . . . ?
C10 C9 C14 C13 -0.4(8) . . . . ?
C10 C11 C12 C13 -1.6(10) . . . . ?
C11 C12 C13 C14 1.6(10) . . . . ?
C12 C13 C14 C9 -0.7(10) . . . . ?
C14 C9 C10 C11 0.5(8) . . . . ?

_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 2.033
_oxdiff_exptl_absorpt_empirical_full_min 0.670
