# 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_tx9596
_database_code_depnum_ccdc_archive 'CCDC 2118506'
loop_
_audit_author_name
_audit_author_address
wangman
;Qingdao University of Science and Techlogy
China
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-05-06 downloaded from the CCDC.
;
_audit_creation_date             2021-10-28
_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         'C23 H29 I N O3'
_chemical_formula_sum            'C23 H29 I N O3'
_chemical_formula_weight         494.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOI
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      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                   10.39180(10)
_cell_length_b                   11.83830(10)
_cell_length_c                   18.4714(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.7990(10)
_cell_angle_gamma                90
_cell_volume                     2196.99(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24868
_cell_measurement_temperature    169.97(12)
_cell_measurement_theta_max      74.8550
_cell_measurement_theta_min      2.4450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    11.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (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    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29836
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.295
_diffrn_reflns_theta_min         4.464
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.97(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00 -71.00   0.50    0.05    --  -47.57 -65.00 110.00   58
  2  ω    -17.00  16.00   0.50    0.05    --  -47.57  65.00-114.00   66
  3  ω    -64.00 -18.00   0.50    0.05    --  -47.57  65.00-114.00   92
  4  ω    -68.00 -41.00   0.50    0.05    --  -47.57 -65.00 110.00   54
  5  ω    -74.00 -49.00   0.50    0.05    --  -99.00  65.00-114.00   50
  6  ω   -149.00-124.00   0.50    0.05    --  -99.00 -65.00 110.00   50
  7  ω    127.00 167.00   0.50    0.05    --  103.25  65.00-114.00   80
  8  ω     31.00  81.00   0.50    0.05    --  103.25 -65.00 110.00  100
  9  ω    -22.00  27.00   0.50    0.05    --  -47.57  19.00-120.00   98
 10  ω    -39.00  25.00   0.50    0.05    --  -47.57  38.00 120.00  128
 11  ω   -119.00 -77.00   0.50    0.05    --  -47.57-125.00 -90.00   84
 12  ω     51.00  76.00   0.50    0.05    --   47.57  65.00-114.00   50
 13  ω      9.00  46.00   0.50    0.05    --   47.57 -65.00 110.00   74
 14  ω     20.00  91.00   0.50    0.05    --   47.57-125.00 120.00  142
 15  ω    -23.00   4.00   0.50    0.05    --   47.57 -65.00 110.00   54
 16  ω     40.00 123.00   0.50    0.05    --   47.57  19.00  60.00  166
 17  ω    -65.00 -27.00   0.50    0.05    --  -99.00  61.00  30.00   76
 18  ω    -67.00 -41.00   0.50    0.05    --  -99.00  61.00 -90.00   52
 19  ω   -167.00 -86.00   0.50    0.05    --  -99.00 -30.00 -60.00  162
 20  ω    -59.00 -32.00   0.50    0.05    --  -99.00  61.00 120.00   54
 21  ω   -165.00-126.00   0.50    0.05    --  -99.00 -61.00  30.00   78
 22  ω   -166.00 -87.00   0.50    0.05    --  -99.00 -61.00   0.00  158
 23  ω    -67.00 -32.00   0.50    0.05    --  -99.00  61.00 -30.00   70
 24  ω    -67.00 -26.00   0.50    0.05    --  -99.00  61.00-120.00   82
 25  ω   -126.00 -99.00   0.50    0.05    --  -99.00 -15.00  30.00   54
 26  ω   -110.00 -82.00   0.50    0.05    --  -99.00 -61.00  30.00   56
 27  ω    -68.00 -27.00   0.50    0.05    --  -99.00  61.00   0.00   82
 28  ω   -153.00 -86.00   0.50    0.05    --  -99.00 -15.00   0.00  134
 29  ω   -165.00-137.00   0.50    0.05    --  -99.00 -15.00  30.00   56
 30  ω    -65.00 -26.00   0.50    0.05    --  -99.00  61.00 -60.00   78
 31  ω   -117.00 -91.00   0.50    0.05    --  -99.00 -45.00   0.00   52
 32  ω     32.00  75.00   0.50    0.05    --  103.25 -61.00  60.00   86
 33  ω    101.00 128.00   0.50    0.05    --  103.25  61.00 -60.00   54
 34  ω     32.00  98.00   0.50    0.05    --  103.25 -94.00-150.00  132
 35  ω     90.00 159.00   0.50    0.05    --  103.25  61.00 150.00  138
 36  ω    131.00 157.00   0.50    0.05    --  103.25  61.00 -60.00   52
 37  ω     61.00 106.00   0.50    0.05    --  103.25 -94.00   0.00   90
 38  ω     95.00 168.00   0.50    0.05    --  103.25  45.00-120.00  146
 39  ω     79.00 105.00   0.50    0.05    --  103.25-125.00-150.00   52
 40  ω    140.00 168.00   0.50    0.05    --  103.25  61.00   0.00   56
 41  ω     36.00  61.00   0.50    0.05    --  103.25-125.00-150.00   50
 42  ω     93.00 136.00   0.50    0.05    --  103.25  45.00 150.00   86
 43  ω     47.00  75.00   0.50    0.05    --  103.25 -61.00  30.00   56
 44  ω     96.00 169.00   0.50    0.05    --  103.25  45.00-180.00  146
 45  ω     80.00 105.00   0.50    0.05    --  103.25 -94.00 -90.00   50
 46  ω    135.00 169.00   0.50    0.05    --  103.25  45.00 -90.00   68
 47  ω     99.00 127.00   0.50    0.05    --  103.25  45.00 -90.00   56
 48  ω     32.00  90.00   0.50    0.05    --  103.25 -94.00-180.00  116
 49  ω     38.00  64.00   0.50    0.05    --  103.25 -61.00 -90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0829132000
_diffrn_orient_matrix_UB_12      0.0970884000
_diffrn_orient_matrix_UB_13      0.0204593000
_diffrn_orient_matrix_UB_21      0.0850694000
_diffrn_orient_matrix_UB_22      -0.0039103000
_diffrn_orient_matrix_UB_23      0.0816003000
_diffrn_orient_matrix_UB_31      0.0968581000
_diffrn_orient_matrix_UB_32      0.0866299000
_diffrn_orient_matrix_UB_33      -0.0191828000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4368
_reflns_number_total             4450
_reflns_odcompleteness_completeness 100.00
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.194
_refine_diff_density_min         -0.791
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4450
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.078
_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)+(0.0517P)²+1.3761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0811
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_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 0.88437(2) 0.36763(2) 0.03418(2) 0.03271(8) Uani 1 1 d . . . . .
O1 O 0.70759(13) 0.30079(12) 0.44966(8) 0.0213(3) Uani 1 1 d . . . . .
O2 O 0.75167(15) 0.25888(12) 0.33719(8) 0.0235(3) Uani 1 1 d . . . . .
O3 O 0.53428(16) 0.46788(14) 0.31553(9) 0.0321(4) Uani 1 1 d . . . . .
N1 N 0.82818(16) 0.33977(15) 0.50490(9) 0.0202(3) Uani 1 1 d . . . . .
H1 H 0.884764 0.379286 0.478016 0.024 Uiso 1 1 calc R U . . .
C1 C 0.7823(2) 0.42367(18) 0.55373(11) 0.0243(4) Uani 1 1 d . . . . .
C2 C 0.9066(2) 0.4590(2) 0.61422(13) 0.0321(5) Uani 1 1 d . . . . .
H2A H 0.966254 0.499856 0.590814 0.038 Uiso 1 1 calc R U . . .
H2B H 0.880492 0.509928 0.649089 0.038 Uiso 1 1 calc R U . . .
C3 C 0.9805(3) 0.3591(2) 0.65724(15) 0.0356(6) Uani 1 1 d . . . . .
H3A H 1.059604 0.385151 0.693663 0.043 Uiso 1 1 calc R U . . .
H3B H 0.923984 0.320561 0.683797 0.043 Uiso 1 1 calc R U . . .
C4 C 1.0193(2) 0.2786(2) 0.60237(14) 0.0336(5) Uani 1 1 d . . . . .
H4A H 1.064254 0.213818 0.629732 0.040 Uiso 1 1 calc R U . . .
H4B H 1.081744 0.316324 0.579464 0.040 Uiso 1 1 calc R U . . .
C5 C 0.9003(2) 0.2368(2) 0.54027(12) 0.0260(5) Uani 1 1 d . . . . .
C6 C 0.7304(3) 0.5278(2) 0.50621(14) 0.0362(5) Uani 1 1 d . . . . .
H6A H 0.795784 0.552556 0.481180 0.054 Uiso 1 1 calc R U . . .
H6B H 0.713408 0.587220 0.537912 0.054 Uiso 1 1 calc R U . . .
H6C H 0.649480 0.509014 0.469721 0.054 Uiso 1 1 calc R U . . .
C7 C 0.6718(3) 0.3826(2) 0.58846(15) 0.0345(5) Uani 1 1 d . . . . .
H7A H 0.602247 0.348204 0.550451 0.052 Uiso 1 1 calc R U . . .
H7B H 0.636301 0.445564 0.609809 0.052 Uiso 1 1 calc R U . . .
H7C H 0.707497 0.328218 0.626907 0.052 Uiso 1 1 calc R U . . .
C8 C 0.9552(3) 0.1770(2) 0.48098(15) 0.0396(6) Uani 1 1 d . . . . .
H8A H 0.883235 0.143551 0.444065 0.059 Uiso 1 1 calc R U . . .
H8B H 1.016649 0.119232 0.504395 0.059 Uiso 1 1 calc R U . . .
H8C H 1.000311 0.230914 0.457317 0.059 Uiso 1 1 calc R U . . .
C9 C 0.8172(3) 0.1514(2) 0.57155(16) 0.0380(6) Uani 1 1 d . . . . .
H9A H 0.802432 0.179854 0.617440 0.057 Uiso 1 1 calc R U . . .
H9B H 0.863950 0.080821 0.580950 0.057 Uiso 1 1 calc R U . . .
H9C H 0.733117 0.140151 0.535827 0.057 Uiso 1 1 calc R U . . .
C10 C 0.7037(2) 0.34367(18) 0.37910(11) 0.0211(4) Uani 1 1 d . . . . .
H10 H 0.759027 0.411655 0.383623 0.025 Uiso 1 1 calc R U . . .
C11 C 0.78925(19) 0.29220(17) 0.27429(11) 0.0204(4) Uani 1 1 d . . . . .
C12 C 0.84335(19) 0.20806(18) 0.23855(11) 0.0213(4) Uani 1 1 d . . . . .
H12 H 0.858646 0.136548 0.259860 0.026 Uiso 1 1 calc R U . . .
C13 C 0.8746(2) 0.23015(18) 0.17145(12) 0.0231(4) Uani 1 1 d . . . . .
H13 H 0.909244 0.173284 0.147261 0.028 Uiso 1 1 calc R U . . .
C14 C 0.8539(2) 0.33739(19) 0.14037(11) 0.0229(4) Uani 1 1 d . . . . .
C15 C 0.8056(2) 0.42323(19) 0.17733(13) 0.0276(4) Uani 1 1 d . . . . .
H15 H 0.795085 0.495737 0.157303 0.033 Uiso 1 1 calc R U . . .
C16 C 0.7730(2) 0.40062(19) 0.24444(12) 0.0258(4) Uani 1 1 d . . . . .
H16 H 0.740458 0.457953 0.269259 0.031 Uiso 1 1 calc R U . . .
C17 C 0.5574(2) 0.37247(17) 0.34008(13) 0.0225(4) Uani 1 1 d . . . . .
C18 C 0.4503(2) 0.28705(19) 0.33243(11) 0.0232(4) Uani 1 1 d . . . . .
C19 C 0.3200(2) 0.3228(2) 0.29949(13) 0.0315(5) Uani 1 1 d . . . . .
H19 H 0.303919 0.397529 0.284399 0.038 Uiso 1 1 calc R U . . .
C20 C 0.2153(2) 0.2475(3) 0.28930(15) 0.0407(6) Uani 1 1 d . . . . .
H20 H 0.128675 0.271886 0.268361 0.049 Uiso 1 1 calc R U . . .
C21 C 0.2394(3) 0.1358(2) 0.31029(17) 0.0407(6) Uani 1 1 d . . . . .
H21 H 0.168881 0.085072 0.302641 0.049 Uiso 1 1 calc R U . . .
C22 C 0.3673(3) 0.0989(2) 0.34251(14) 0.0346(5) Uani 1 1 d . . . . .
H22 H 0.382746 0.023599 0.356233 0.042 Uiso 1 1 calc R U . . .
C23 C 0.4732(2) 0.1750(2) 0.35443(12) 0.0266(4) Uani 1 1 d . . . . .
H23 H 0.559149 0.150690 0.377104 0.032 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 C14 2.096(2) . ?
O1 N1 1.474(2) . ?
O1 C10 1.390(2) . ?
O2 C10 1.433(2) . ?
O2 C11 1.375(2) . ?
O3 C17 1.218(3) . ?
N1 H1 0.9800 . ?
N1 C1 1.499(3) . ?
N1 C5 1.492(3) . ?
C1 C2 1.535(3) . ?
C1 C6 1.529(3) . ?
C1 C7 1.531(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.520(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.519(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.538(3) . ?
C5 C8 1.531(3) . ?
C5 C9 1.535(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C17 1.546(3) . ?
C11 C12 1.391(3) . ?
C11 C16 1.390(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(3) . ?
C14 C15 1.388(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.392(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.483(3) . ?
C18 C19 1.400(3) . ?
C18 C23 1.390(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.382(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.381(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.395(3) . ?
C23 H23 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
C10 O1 N1 110.53(14) . . ?
C11 O2 C10 117.95(16) . . ?
O1 N1 H1 108.2 . . ?
O1 N1 C1 106.21(14) . . ?
O1 N1 C5 106.90(15) . . ?
C1 N1 H1 108.2 . . ?
C5 N1 H1 108.2 . . ?
C5 N1 C1 118.65(16) . . ?
N1 C1 C2 106.30(17) . . ?
N1 C1 C6 107.96(17) . . ?
N1 C1 C7 115.44(19) . . ?
C6 C1 C2 107.80(19) . . ?
C6 C1 C7 107.7(2) . . ?
C7 C1 C2 111.34(19) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 C1 112.77(19) . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C2 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 C2 108.9(2) . . ?
C4 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C3 C4 C5 113.6(2) . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
N1 C5 C4 106.38(19) . . ?
N1 C5 C8 107.55(18) . . ?
N1 C5 C9 115.78(18) . . ?
C8 C5 C4 107.85(19) . . ?
C8 C5 C9 108.3(2) . . ?
C9 C5 C4 110.71(19) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 O2 108.68(16) . . ?
O1 C10 H10 110.1 . . ?
O1 C10 C17 107.88(17) . . ?
O2 C10 H10 110.1 . . ?
O2 C10 C17 109.83(16) . . ?
C17 C10 H10 110.1 . . ?
O2 C11 C12 115.61(18) . . ?
O2 C11 C16 124.64(18) . . ?
C16 C11 C12 119.72(19) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.36(19) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.78(19) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 I1 119.95(16) . . ?
C13 C14 C15 120.25(19) . . ?
C15 C14 I1 119.69(16) . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.9(2) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 119.9(2) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
O3 C17 C10 117.1(2) . . ?
O3 C17 C18 121.7(2) . . ?
C18 C17 C10 121.27(18) . . ?
C19 C18 C17 117.0(2) . . ?
C23 C18 C17 123.66(19) . . ?
C23 C18 C19 119.3(2) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.9(2) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.8(2) . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C22 120.0(2) . . ?
C18 C23 H23 120.0 . . ?
C22 C23 H23 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
I1 C14 C15 C16 173.75(17) . . . . ?
O1 N1 C1 C2 176.67(16) . . . . ?
O1 N1 C1 C6 -67.9(2) . . . . ?
O1 N1 C1 C7 52.7(2) . . . . ?
O1 N1 C5 C4 -175.25(16) . . . . ?
O1 N1 C5 C8 69.4(2) . . . . ?
O1 N1 C5 C9 -51.8(2) . . . . ?
O1 C10 C17 O3 126.5(2) . . . . ?
O1 C10 C17 C18 -54.0(3) . . . . ?
O2 C10 C17 O3 -115.2(2) . . . . ?
O2 C10 C17 C18 64.3(3) . . . . ?
O2 C11 C12 C13 174.78(17) . . . . ?
O2 C11 C16 C15 -175.26(19) . . . . ?
O3 C17 C18 C19 -3.6(3) . . . . ?
O3 C17 C18 C23 174.9(2) . . . . ?
N1 O1 C10 O2 98.41(17) . . . . ?
N1 O1 C10 C17 -142.56(15) . . . . ?
N1 C1 C2 C3 -55.1(3) . . . . ?
C1 N1 C5 C4 -55.4(2) . . . . ?
C1 N1 C5 C8 -170.70(19) . . . . ?
C1 N1 C5 C9 68.1(3) . . . . ?
C1 C2 C3 C4 57.8(3) . . . . ?
C2 C3 C4 C5 -57.0(3) . . . . ?
C3 C4 C5 N1 53.5(3) . . . . ?
C3 C4 C5 C8 168.7(2) . . . . ?
C3 C4 C5 C9 -73.0(3) . . . . ?
C5 N1 C1 C2 56.4(2) . . . . ?
C5 N1 C1 C6 171.87(18) . . . . ?
C5 N1 C1 C7 -67.6(2) . . . . ?
C6 C1 C2 C3 -170.7(2) . . . . ?
C7 C1 C2 C3 71.4(3) . . . . ?
C10 O1 N1 C1 108.62(17) . . . . ?
C10 O1 N1 C5 -123.79(17) . . . . ?
C10 O2 C11 C12 175.84(17) . . . . ?
C10 O2 C11 C16 -6.1(3) . . . . ?
C10 C17 C18 C19 177.0(2) . . . . ?
C10 C17 C18 C23 -4.5(3) . . . . ?
C11 O2 C10 O1 -163.18(16) . . . . ?
C11 O2 C10 C17 79.0(2) . . . . ?
C11 C12 C13 C14 1.2(3) . . . . ?
C12 C11 C16 C15 2.7(3) . . . . ?
C12 C13 C14 I1 -174.39(15) . . . . ?
C12 C13 C14 C15 1.8(3) . . . . ?
C13 C14 C15 C16 -2.4(3) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C16 C11 C12 C13 -3.4(3) . . . . ?
C17 C18 C19 C20 178.9(2) . . . . ?
C17 C18 C23 C22 -177.4(2) . . . . ?
C18 C19 C20 C21 -1.3(4) . . . . ?
C19 C18 C23 C22 1.0(3) . . . . ?
C19 C20 C21 C22 1.0(4) . . . . ?
C20 C21 C22 C23 0.3(4) . . . . ?
C21 C22 C23 C18 -1.4(4) . . . . ?
C23 C18 C19 C20 0.3(3) . . . . ?

_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 2.968
_oxdiff_exptl_absorpt_empirical_full_min 0.609
