# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_hubu-lyj-tpt-jacs-20190512
_database_code_depnum_ccdc_archive 'CCDC 1918655'
loop_
_audit_author_name
_audit_author_address
'Li jiawei'
;HUBU university
China
;
_audit_update_record             
;
2019-05-26 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_audit_creation_date             2019-05-26
_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         'C17 H13 I O4'
_chemical_formula_sum            'C17 H13 I O4'
_chemical_formula_weight         408.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'I C O N H'
_chemical_oxdiff_usercomment     colorless
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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5534(3)
_cell_length_b                   9.6302(3)
_cell_length_c                   10.2451(2)
_cell_angle_alpha                74.922(2)
_cell_angle_beta                 85.722(2)
_cell_angle_gamma                61.931(3)
_cell_volume                     801.80(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9496
_cell_measurement_temperature    100
_cell_measurement_theta_max      76.4640
_cell_measurement_theta_min      4.4100
_shelx_estimated_absorpt_T_max   0.144
_shelx_estimated_absorpt_T_min   0.144
_exptl_absorpt_coefficient_mu    15.828
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16140
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.634
_diffrn_reflns_theta_min         4.477
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  59.00   0.50    0.17    --   43.80 -55.00  43.00  166
  2  ω     92.00 120.00   0.50    0.69    --  111.75 -55.00  43.00   56
  3  ω     75.00 139.00   0.50    0.69    --  111.75 -77.00  60.00  128
  4  ω     64.00 177.00   0.50    0.69    --  111.75  15.00  30.00  226
  5  ω     94.00 176.00   0.50    0.69    --  111.75  45.00 -90.00  164
  6  ω     95.00 177.00   0.50    0.69    --  111.75  77.00-150.00  164
  7  ω     91.00 176.00   0.50    0.69    --  111.75  55.00-173.00  170
  8  ω     61.00  88.00   0.50    0.17    --   43.80  55.00-173.00   54
  9  ω     24.00  50.00   0.50    0.17    --   43.80  55.00-173.00   52
 10  ω     17.00  58.00   0.50    0.17    --   43.80  77.00 -90.00   82
 11  ω     17.00  61.00   0.50    0.17    --   43.80  78.00-164.72   88
 12  ω      0.00  29.00   0.50    0.17    --  -43.80  55.00-173.00   58
 13  ω    -34.00  -2.00   0.50    0.17    --  -43.80  55.00-173.00   64
 14  ω    -78.00 -21.00   0.50    0.17    --  -43.80 -57.00 -30.00  114
 15  ω    -43.00 -18.00   0.50    0.17    --  -43.80 -77.00 -30.00   50
 16  ω    -52.00 -15.00   0.50    0.17    --  -43.80 -77.00  60.00   74
 17  ω    -61.00 -27.00   0.50    0.17    --  -43.80 -37.00  60.00   68
 18  ω    -68.00 -24.00   0.50    0.17    --  -43.80 -55.00  43.00   88
 19  ω    -66.00 -19.00   0.50    0.17    --  -43.80 -77.00 -60.00   94
 20  ω    -87.00 -61.00   0.50    0.69    --  -90.25 -77.00-150.00   52
 21  ω    -87.00 -60.00   0.50    0.69    --  -90.25 -82.00-151.41   54
 22  ω    -92.00 -61.00   0.50    0.69    --  -90.25 -77.00-110.46   62
 23  ω    -87.00 -61.00   0.50    0.69    --  -90.25 -77.00 -60.00   52
 24  ω    -91.00 -64.00   0.50    0.69    --  -90.25 -77.00   0.00   54
 25  ω    -90.00 -61.00   0.50    0.69    --  -90.25 -77.00  30.00   58
 26  ω    -87.00 -62.00   0.50    0.69    --  -90.25 -74.00  84.53   50
 27  ω    -91.00 -60.00   0.50    0.69    --  -90.25 -79.00 111.17   62
 28  ω   -104.00 -63.00   0.50    0.69    --  -90.25 -75.00  74.77   82
 29  ω    -92.00 -59.00   0.50    0.69    --  -90.25 -81.00  63.03   66
 30  ω    -98.00 -62.00   0.50    0.69    --  -90.25 -74.00 -15.60   72
 31  ω   -106.00 -68.00   0.50    0.69    --  -90.25 -57.00  20.43   76
 32  ω    -98.00 -62.00   0.50    0.69    --  -90.25 -77.00 -30.00   72
 33  ω    -94.00 -62.00   0.50    0.69    --  -90.25 -74.00 -76.74   64
 34  ω   -101.00 -59.00   0.50    0.69    --  -90.25 -81.00-125.94   84
 35  ω   -114.00 -16.00   0.50    0.17    --  -43.80 -19.00-180.00  196
 36  ω    -88.00 -63.00   0.50    0.69    --  -90.25  55.00-173.00   50
 37  ω   -118.00 -15.00   0.50    0.17    --  -43.80 -77.00-180.00  206
 38  ω     31.00  97.00   0.50    0.17    --   43.80-125.00 -90.00  132
 39  ω     39.00  82.00   0.50    0.69    --  111.75 -55.00  43.00   86
 40  ω     39.00 106.00   0.50    0.69    --  111.75 -94.00  30.00  134
 41  ω     39.00 117.00   0.50    0.69    --  111.75-125.00 -60.00  156
 42  ω     41.00 121.00   0.50    0.69    --  111.75-125.00-120.00  160
 43  ω     44.00 103.00   0.50    0.69    --  111.75 -94.00 -30.00  118
 44  ω     89.00 177.00   0.50    0.69    --  111.75  61.00 120.00  176
 45  ω    147.00 174.00   0.50    0.69    --  111.75 125.00 120.00   54
 46  ω    107.00 143.00   0.50    0.69    --  111.75 125.00 120.00   72
 47  ω     86.00 176.00   0.50    0.69    --  111.75  77.00  60.00  180
 48  ω    -95.00 -59.00   0.50    0.69    --  -90.25 -82.00 177.82   72
 49  ω   -101.00 -59.00   0.50    0.69    --  -90.25 -81.00 133.69   84
 50  ω   -114.00 -77.00   0.50    0.17    --  -43.80 -55.00  43.00   74
 51  ω   -111.00 -61.00   0.50    0.69    --  -90.25 -77.00-180.00  100
 52  ω   -109.00 -62.00   0.50    0.69    --  -90.25 -77.00 -90.00   94
 53  ω   -131.00 -68.00   0.50    0.69    --  -90.25 -61.00 -60.00  126
 54  ω   -122.00 -95.00   0.50    0.69    --  -90.25 -77.00-150.00   54
 55  ω   -158.00-132.00   0.50    0.69    --  -90.25 -77.00-110.46   52
 56  ω   -159.00-134.00   0.50    0.69    --  -90.25 -77.00 -90.00   50
 57  ω   -158.00-131.00   0.50    0.69    --  -90.25 -77.00 -30.00   54
 58  ω   -134.00 -64.00   0.50    0.69    --  -90.25 -70.00   0.67  140
 59  ω   -121.00 -64.00   0.50    0.17    --  -43.80 -37.00  60.00  114
 60  ω   -124.00 -61.00   0.50    0.69    --  -90.25 -77.00 150.00  126
 61  ω   -140.00-113.00   0.50    0.69    --  -90.25 -74.00  84.53   54
 62  ω   -140.00-113.00   0.50    0.69    --  -90.25 -77.00  30.00   54
 63  ω   -163.00-113.00   0.50    0.69    --  -90.25 -55.00  43.00  100
 64  ω   -151.00-123.00   0.50    0.69    --  -90.25 -81.00 133.69   56
 65  ω   -162.00-130.00   0.50    0.69    --  -90.25 -75.00  74.77   64
 66  ω   -164.00-108.00   0.50    0.69    --  -90.25 -79.00 111.17  112
 67  ω   -160.00-133.00   0.50    0.69    --  -90.25 -81.00-125.94   54
 68  ω   -163.00-104.00   0.50    0.69    --  -90.25-125.00-180.00  118
 69  ω   -109.00 -16.00   0.50    0.69    --  -90.25  77.00 150.00  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1726221000
_diffrn_orient_matrix_UB_12      -0.0663760000
_diffrn_orient_matrix_UB_13      -0.0434945000
_diffrn_orient_matrix_UB_21      0.0402530000
_diffrn_orient_matrix_UB_22      -0.1688262000
_diffrn_orient_matrix_UB_23      0.0942076000
_diffrn_orient_matrix_UB_31      -0.0456662000
_diffrn_orient_matrix_UB_32      -0.0475432000
_diffrn_orient_matrix_UB_33      -0.1164583000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3043
_reflns_number_total             3261
_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 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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         1.049
_refine_diff_density_min         -1.272
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.081
_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)+(0.0607P)²+0.8048P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1074
_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 Ternary CH refined with riding coordinates:
 C14(H14), C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10), C8(H8), C4(H4), C9(H9), C1(H1), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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 0.70697(3) 0.46562(3) 0.88738(3) 0.05572(13) Uani 1 1 d . . . . .
O2 O 0.5173(3) 0.3284(3) 0.6031(2) 0.0386(5) Uani 1 1 d . . . . .
O4 O 0.8896(3) 0.3633(4) 0.5897(3) 0.0528(7) Uani 1 1 d . . . . .
O1 O 0.4451(4) 0.1936(4) 0.5057(3) 0.0576(8) Uani 1 1 d . . . . .
O3 O 0.8557(4) 0.1532(3) 0.7125(4) 0.0654(9) Uani 1 1 d . . . . .
C14 C 0.5269(4) 0.3743(4) 0.7256(3) 0.0340(6) Uani 1 1 d . . . . .
H14 H 0.5612 0.2767 0.8046 0.041 Uiso 1 1 calc R . . . .
C12 C 0.3614(4) 0.5010(4) 0.7450(3) 0.0350(7) Uani 1 1 d . . . . .
C15 C 0.6555(4) 0.4273(4) 0.7021(3) 0.0359(7) Uani 1 1 d . . . . .
H15 H 0.6194 0.5298 0.6279 0.043 Uiso 1 1 calc R . . . .
C7 C 0.2507(4) 0.4446(4) 0.7899(4) 0.0362(7) Uani 1 1 d . . . . .
C11 C 0.3150(4) 0.6664(4) 0.7138(4) 0.0415(8) Uani 1 1 d . . . . .
H11 H 0.3899 0.7043 0.6817 0.050 Uiso 1 1 calc R . . . .
C5 C 0.3952(4) 0.1673(4) 0.7396(4) 0.0376(7) Uani 1 1 d . . . . .
C6 C 0.2968(4) 0.2682(4) 0.8208(4) 0.0387(7) Uani 1 1 d . . . . .
C13 C 0.4531(4) 0.2285(4) 0.6080(4) 0.0406(7) Uani 1 1 d . . . . .
C16 C 0.8102(4) 0.2965(5) 0.6695(4) 0.0426(8) Uani 1 1 d . . . . .
C10 C 0.1597(5) 0.7763(4) 0.7294(4) 0.0492(9) Uani 1 1 d . . . . .
H10 H 0.1286 0.8893 0.7089 0.059 Uiso 1 1 calc R . . . .
C8 C 0.0950(5) 0.5573(5) 0.8038(4) 0.0477(8) Uani 1 1 d . . . . .
H8 H 0.0184 0.5211 0.8338 0.057 Uiso 1 1 calc R . . . .
C4 C 0.4296(5) 0.0036(4) 0.7701(4) 0.0476(9) Uani 1 1 d . . . . .
H4 H 0.4946 -0.0634 0.7135 0.057 Uiso 1 1 calc R . . . .
C9 C 0.0508(5) 0.7220(5) 0.7744(5) 0.0518(9) Uani 1 1 d . . . . .
H9 H -0.0554 0.7976 0.7855 0.062 Uiso 1 1 calc R . . . .
C1 C 0.2346(5) 0.2003(5) 0.9317(4) 0.0489(9) Uani 1 1 d . . . . .
H1 H 0.1659 0.2671 0.9870 0.059 Uiso 1 1 calc R . . . .
C3 C 0.3689(6) -0.0604(5) 0.8829(5) 0.0547(10) Uani 1 1 d . . . . .
H3 H 0.3949 -0.1722 0.9052 0.066 Uiso 1 1 calc R . . . .
C2 C 0.2706(6) 0.0381(5) 0.9628(5) 0.0577(10) Uani 1 1 d . . . . .
H2 H 0.2277 -0.0055 1.0393 0.069 Uiso 1 1 calc R . . . .
C17 C 1.0487(5) 0.2509(7) 0.5623(6) 0.0683(13) Uani 1 1 d . . . . .
H17A H 1.0994 0.3123 0.5068 0.102 Uiso 1 1 calc GR . . . .
H17B H 1.0427 0.1785 0.5136 0.102 Uiso 1 1 calc GR . . . .
H17C H 1.1114 0.1860 0.6479 0.102 Uiso 1 1 calc GR . . . .


_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 C15 2.157(3) . ?
O2 C14 1.457(4) . ?
O2 C13 1.352(4) . ?
O4 C16 1.324(5) . ?
O4 C17 1.451(5) . ?
O1 C13 1.199(5) . ?
O3 C16 1.198(5) . ?
C14 C12 1.514(4) . ?
C14 C15 1.520(5) . ?
C12 C7 1.401(5) . ?
C12 C11 1.388(5) . ?
C15 C16 1.508(5) . ?
C7 C6 1.489(5) . ?
C7 C8 1.394(5) . ?
C11 C10 1.387(5) . ?
C5 C6 1.401(5) . ?
C5 C13 1.501(5) . ?
C5 C4 1.401(5) . ?
C6 C1 1.397(5) . ?
C10 C9 1.372(6) . ?
C8 C9 1.387(6) . ?
C4 C3 1.385(6) . ?
C1 C2 1.382(6) . ?
C3 C2 1.380(7) . ?

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
C13 O2 C14 118.9(3) . . ?
C16 O4 C17 115.8(3) . . ?
O2 C14 C12 106.9(3) . . ?
O2 C14 C15 104.8(3) . . ?
C12 C14 C15 117.0(3) . . ?
C7 C12 C14 116.5(3) . . ?
C11 C12 C14 123.3(3) . . ?
C11 C12 C7 120.2(3) . . ?
C14 C15 I1 108.9(2) . . ?
C16 C15 I1 105.4(2) . . ?
C16 C15 C14 111.9(3) . . ?
C12 C7 C6 121.1(3) . . ?
C8 C7 C12 118.6(3) . . ?
C8 C7 C6 120.2(3) . . ?
C10 C11 C12 120.2(3) . . ?
C6 C5 C13 123.5(3) . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 C13 115.6(3) . . ?
C5 C6 C7 122.8(3) . . ?
C1 C6 C7 119.2(3) . . ?
C1 C6 C5 117.9(3) . . ?
O2 C13 C5 119.0(3) . . ?
O1 C13 O2 117.8(3) . . ?
O1 C13 C5 123.2(3) . . ?
O4 C16 C15 110.0(3) . . ?
O3 C16 O4 125.2(4) . . ?
O3 C16 C15 124.7(3) . . ?
C9 C10 C11 120.1(3) . . ?
C9 C8 C7 120.6(4) . . ?
C3 C4 C5 120.0(4) . . ?
C10 C9 C8 120.3(3) . . ?
C2 C1 C6 121.5(4) . . ?
C2 C3 C4 120.1(4) . . ?
C3 C2 C1 120.1(4) . . ?

_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 1.623
_oxdiff_exptl_absorpt_empirical_full_min 0.664
####################################################################### 
# 
# 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_tpt-14-8
_database_code_depnum_ccdc_archive 'CCDC 1974644'
loop_
_audit_author_name
_audit_author_address
'Panting '
;Hubei University
China
;
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_audit_creation_date             2019-06-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 F I O4'
_chemical_formula_sum            'C18 H14 F I O4'
_chemical_formula_weight         440.19
_chemical_absolute_configuration S
_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'
F F 0.0171 0.0103 '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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.7643(3)
_cell_length_b                   9.1745(3)
_cell_length_c                   20.1935(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1623.72(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4665
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      28.1280
_cell_measurement_theta_min      2.0070
_shelx_estimated_absorpt_T_max   0.690
_shelx_estimated_absorpt_T_min   0.690
_exptl_absorpt_coefficient_mu    2.002
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9747
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.770
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.378
_diffrn_reflns_theta_min         2.017
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  59.00   0.50    0.97    --   -9.20  57.00 -30.00  166
  2  ω    -16.00  10.00   0.50    0.97    --   -9.20 -37.00  24.00   52
  3  ω    -25.00   5.00   0.50    0.97    --   -9.20 -99.00 -60.00   60
  4  ω    -85.00 -29.00   0.50    0.97    --   -9.20 -37.00  24.00  112
  5  ω      1.00  26.00   0.50    0.97    --   -9.20  57.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0683832000
_diffrn_orient_matrix_UB_12      0.0079174000
_diffrn_orient_matrix_UB_13      0.0184605000
_diffrn_orient_matrix_UB_21      0.0412122000
_diffrn_orient_matrix_UB_22      -0.0352736000
_diffrn_orient_matrix_UB_23      -0.0256252000
_diffrn_orient_matrix_UB_31      0.0133403000
_diffrn_orient_matrix_UB_32      0.0683318000
_diffrn_orient_matrix_UB_33      -0.0153618000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.626
_reflns_Friedel_fraction_full    0.915
_reflns_Friedel_fraction_max     0.688
_reflns_number_gt                3468
_reflns_number_total             3767
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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         0.508
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3767
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.021
_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)+(0.0157P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0566
_refine_ls_wR_factor_ref         0.0597
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.50(3)
 0.50(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C4(H4), C3(H3)
3.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C6(H6), C8(H8), C9(H9), C17(H17), C14(H14)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C1(H1A,H1B,H1C)
;
_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 0.51329(3) 0.91245(3) 0.52865(2) 0.02284(9) Uani 1 1 d . . . . .
O1 O 0.3802(5) 0.6416(4) 0.41144(18) 0.0287(10) Uani 1 1 d . . . . .
O3 O 0.5417(4) 0.4450(3) 0.54928(14) 0.0198(7) Uani 1 1 d . . . . .
F1 F 0.2304(4) 0.7240(3) 0.74936(13) 0.0338(7) Uani 1 1 d . . . . .
O4 O 0.6110(5) 0.2167(3) 0.55755(17) 0.0275(9) Uani 1 1 d . . . . .
O2 O 0.6325(4) 0.6237(4) 0.42588(18) 0.0340(10) Uani 1 1 d . . . . .
C18 C 0.9176(6) 0.5107(5) 0.6922(2) 0.0227(11) Uani 1 1 d . . . . .
H18 H 0.920602 0.577159 0.726984 0.027 Uiso 1 1 calc R . . . .
C2 C 0.5068(7) 0.6463(4) 0.4468(2) 0.0200(10) Uani 1 1 d . . . . .
C4 C 0.5699(6) 0.5987(5) 0.5660(2) 0.0179(10) Uani 1 1 d . . . . .
H4 H 0.677308 0.623056 0.558183 0.021 Uiso 1 1 calc R . . . .
C12 C 0.6404(6) 0.3419(5) 0.5710(2) 0.0188(10) Uani 1 1 d . . . . .
C6 C 0.3961(6) 0.6724(5) 0.6611(2) 0.0222(11) Uani 1 1 d . . . . .
H6 H 0.325430 0.710758 0.631518 0.027 Uiso 1 1 calc R . . . .
C11 C 0.7808(6) 0.4868(5) 0.6598(2) 0.0184(10) Uani 1 1 d . . . . .
C0AA C 0.5319(6) 0.6154(4) 0.6388(2) 0.0190(11) Uani 1 1 d . . . . .
C3 C 0.4688(6) 0.6825(4) 0.5183(2) 0.0184(10) Uani 1 1 d . . . . .
H3 H 0.361100 0.661764 0.527378 0.022 Uiso 1 1 calc R . . . .
C10 C 0.6380(6) 0.5571(5) 0.6830(2) 0.0209(11) Uani 1 1 d . . . . .
C15 C 1.0503(6) 0.3359(5) 0.6241(2) 0.0247(12) Uani 1 1 d . . . . .
C13 C 0.7801(6) 0.3848(5) 0.6078(2) 0.0178(10) Uani 1 1 d . . . . .
C8 C 0.4687(7) 0.6192(5) 0.7739(2) 0.0275(13) Uani 1 1 d . . . . .
H8 H 0.446865 0.622322 0.818965 0.033 Uiso 1 1 calc R . . . .
C9 C 0.6055(6) 0.5614(5) 0.7514(2) 0.0257(12) Uani 1 1 d . . . . .
H9 H 0.676231 0.525362 0.781593 0.031 Uiso 1 1 calc R . . . .
C16 C 1.1966(6) 0.2599(6) 0.6037(3) 0.0345(13) Uani 1 1 d . . . . .
H16A H 1.242510 0.311564 0.567488 0.052 Uiso 1 1 calc GR . . . .
H16B H 1.174088 0.161859 0.590267 0.052 Uiso 1 1 calc GR . . . .
H16C H 1.265965 0.258096 0.640516 0.052 Uiso 1 1 calc GR . . . .
C7 C 0.3666(7) 0.6715(5) 0.7287(3) 0.0250(12) Uani 1 1 d . . . . .
C17 C 1.0498(6) 0.4389(5) 0.6744(2) 0.0258(12) Uani 1 1 d . . . . .
H17 H 1.140208 0.459886 0.696583 0.031 Uiso 1 1 calc R . . . .
C14 C 0.9125(7) 0.3091(5) 0.5923(3) 0.0222(12) Uani 1 1 d . . . . .
H14 H 0.908862 0.237969 0.559527 0.027 Uiso 1 1 calc R . . . .
C1 C 0.3970(7) 0.6022(6) 0.3420(2) 0.0360(14) Uani 1 1 d . . . . .
H1A H 0.304283 0.624204 0.318726 0.054 Uiso 1 1 calc GR . . . .
H1B H 0.418114 0.499775 0.338480 0.054 Uiso 1 1 calc GR . . . .
H1C H 0.479661 0.656513 0.322914 0.054 Uiso 1 1 calc GR . . . .


_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 C3 2.156(4) . ?
O1 C2 1.320(6) . ?
O1 C1 1.456(5) . ?
O3 C4 1.471(5) . ?
O3 C12 1.355(5) . ?
F1 C7 1.353(6) . ?
O4 C12 1.208(5) . ?
O2 C2 1.199(6) . ?
C18 C11 1.383(7) . ?
C18 C17 1.381(7) . ?
C2 C3 1.518(6) . ?
C4 C0AA 1.515(6) . ?
C4 C3 1.517(6) . ?
C12 C13 1.485(7) . ?
C6 C0AA 1.376(7) . ?
C6 C7 1.389(7) . ?
C11 C10 1.483(7) . ?
C11 C13 1.408(6) . ?
C0AA C10 1.395(7) . ?
C10 C9 1.412(6) . ?
C15 C16 1.517(7) . ?
C15 C17 1.388(7) . ?
C15 C14 1.389(7) . ?
C13 C14 1.388(7) . ?
C8 C9 1.388(8) . ?
C8 C7 1.366(8) . ?

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
C2 O1 C1 116.4(4) . . ?
C12 O3 C4 119.2(4) . . ?
C17 C18 C11 121.9(4) . . ?
O1 C2 C3 109.7(5) . . ?
O2 C2 O1 125.1(4) . . ?
O2 C2 C3 125.1(5) . . ?
O3 C4 C0AA 106.4(3) . . ?
O3 C4 C3 104.0(3) . . ?
C0AA C4 C3 115.8(4) . . ?
O3 C12 C13 120.2(4) . . ?
O4 C12 O3 117.0(4) . . ?
O4 C12 C13 122.7(4) . . ?
C0AA C6 C7 118.8(5) . . ?
C18 C11 C10 120.9(4) . . ?
C18 C11 C13 117.5(4) . . ?
C13 C11 C10 121.4(4) . . ?
C6 C0AA C4 123.1(4) . . ?
C6 C0AA C10 120.8(4) . . ?
C10 C0AA C4 115.8(4) . . ?
C2 C3 I1 105.4(3) . . ?
C4 C3 I1 109.2(3) . . ?
C4 C3 C2 111.4(4) . . ?
C0AA C10 C11 121.8(4) . . ?
C0AA C10 C9 118.8(5) . . ?
C9 C10 C11 119.4(4) . . ?
C17 C15 C16 120.9(5) . . ?
C17 C15 C14 117.1(5) . . ?
C14 C15 C16 121.9(4) . . ?
C11 C13 C12 123.6(4) . . ?
C14 C13 C12 116.4(4) . . ?
C14 C13 C11 119.8(5) . . ?
C7 C8 C9 118.8(4) . . ?
C8 C9 C10 120.4(5) . . ?
F1 C7 C6 117.8(5) . . ?
F1 C7 C8 119.8(5) . . ?
C8 C7 C6 122.5(5) . . ?
C18 C17 C15 121.2(5) . . ?
C13 C14 C15 122.3(4) . . ?

_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 1.658
_oxdiff_exptl_absorpt_empirical_full_min 0.488
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.50(3)
2 0.50(3)

####################################################################### 
# 
# 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_hubu-lyj-tpt-i
_database_code_depnum_ccdc_archive 'CCDC 1944536'
loop_
_audit_author_name
_audit_author_address
'Panting '
;Hubei University
China
;
_audit_update_record             
;
2019-07-31 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_audit_creation_date             2019-06-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 I O4'
_chemical_formula_sum            'C19 H15 I O4'
_chemical_formula_weight         434.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'I C N H O'
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'
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                   8.09310(10)
_cell_length_b                   13.1306(2)
_cell_length_c                   15.5266(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.488(2)
_cell_angle_gamma                90
_cell_volume                     1642.41(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5993
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      75.7390
_cell_measurement_theta_min      4.4070
_shelx_estimated_absorpt_T_max   0.148
_shelx_estimated_absorpt_T_min   0.148
_exptl_absorpt_coefficient_mu    15.498
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9809
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.418
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     22.00  48.00   0.50    0.05    --   43.18  57.00 120.00   52
  2  ω     62.00 114.00   0.50    0.05    --   43.18  57.00 120.00  104
  3  ω     91.00 173.00   0.50    0.06    --  109.88  45.00 -60.00  164
  4  ω    114.00 139.00   0.50    0.06    --  109.88 115.00-157.00   50
  5  ω     97.00 166.00   0.50    0.06    --  109.88 125.00-180.00  138
  6  ω    133.00 159.00   0.50    0.06    --  109.88  45.00-180.00   52
  7  ω     90.00 126.00   0.50    0.06    --  109.88  45.00-180.00   72
  8  ω     88.00 178.00   0.50    0.06    --  109.88  61.00 -90.00  180
  9  ω     85.00 137.00   0.50    0.06    --  109.88 -77.00  90.00  104
 10  ω     83.00 146.00   0.50    0.06    --  109.88-166.00 -33.00  126
 11  ω     34.00  59.00   0.50    0.05    --   43.18-115.00 113.00   50
 12  ω     48.00 109.00   0.50    0.06    --  109.88-115.00 113.00  122
 13  ω     37.00 108.00   0.50    0.06    --  109.88 -94.00 -30.00  142
 14  ω    -93.00 -47.00   0.50    0.05    --  -43.18-166.00 -33.00   92
 15  ω    -64.00 -38.00   0.50    0.06    --  -90.25  61.00  30.00   52
 16  ω    -99.00 -74.00   0.50    0.05    --  -43.18 166.00 -11.00   50
 17  ω    -99.00 -74.00   0.50    0.06    --  -90.25 166.00 -11.00   50
 18  ω    -88.00  -8.00   0.50    0.05    --  -43.18 115.00-157.00  160
 19  ω    -77.00 -52.00   0.50    0.06    --  -90.25 115.00-157.00   50
 20  ω   -109.00 -18.00   0.50    0.05    --  -43.18 -77.00  30.00  182
 21  ω   -139.00 -83.00   0.50    0.06    --  -90.25-115.00 113.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0691118000
_diffrn_orient_matrix_UB_12      -0.1070727000
_diffrn_orient_matrix_UB_13      -0.0225744000
_diffrn_orient_matrix_UB_21      -0.1066144000
_diffrn_orient_matrix_UB_22      0.0442284000
_diffrn_orient_matrix_UB_23      -0.0786396000
_diffrn_orient_matrix_UB_31      0.1428805000
_diffrn_orient_matrix_UB_32      -0.0186191000
_diffrn_orient_matrix_UB_33      -0.0569399000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2753
_reflns_number_total             2932
_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 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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         1.872
_refine_diff_density_min         -2.405
_refine_diff_density_rms         0.283
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     62
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0891P)²+1.4317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1260
_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. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.65428(3) 0.12186(2) 0.61117(2) 0.01366(16) Uani 1 1 d . U . . .
O1 O 0.2444(4) 0.1787(3) 0.5517(2) 0.0241(7) Uani 1 1 d . U . . .
O2 O 0.3828(4) 0.3277(2) 0.55406(19) 0.0177(6) Uani 1 1 d . U . . .
O3 O 0.4813(3) 0.2743(2) 0.37129(17) 0.0130(5) Uani 1 1 d . U . . .
O4 O 0.4018(4) 0.3850(2) 0.2692(2) 0.0171(7) Uani 1 1 d . U . . .
C1 C 0.1214(7) 0.2275(5) 0.6009(4) 0.0344(13) Uani 1 1 d . U . . .
H1A H 0.074245 0.284947 0.569144 0.052 Uiso 1 1 calc GR . . . .
H1B H 0.173802 0.249999 0.655670 0.052 Uiso 1 1 calc GR . . . .
H1C H 0.035256 0.179624 0.610230 0.052 Uiso 1 1 calc GR . . . .
C2 C 0.3710(5) 0.2380(3) 0.5367(3) 0.0136(6) Uani 1 1 d . U . . .
C3 C 0.5051(5) 0.1777(3) 0.4980(3) 0.0126(6) Uani 1 1 d . U . . .
H3 H 0.456069 0.120698 0.463791 0.015 Uiso 1 1 calc R . . . .
C4 C 0.6050(5) 0.2457(3) 0.4422(3) 0.0114(6) Uani 1 1 d . U . . .
H4 H 0.639630 0.307012 0.475158 0.014 Uiso 1 1 calc R . . . .
C5 C 0.7533(5) 0.2010(3) 0.4049(2) 0.0116(6) Uani 1 1 d . U . . .
C6 C 0.7889(6) 0.0974(4) 0.4055(3) 0.0163(8) Uani 1 1 d . U . . .
H6 H 0.718823 0.052104 0.430346 0.020 Uiso 1 1 calc R . . . .
C7 C 0.9277(6) 0.0609(4) 0.3696(3) 0.0212(8) Uani 1 1 d . U . . .
H7 H 0.950688 -0.008494 0.370841 0.025 Uiso 1 1 calc R . . . .
C8 C 1.0320(7) 0.1272(3) 0.3320(4) 0.0227(10) Uani 1 1 d . U . . .
H8 H 1.124682 0.102323 0.307804 0.027 Uiso 1 1 calc R . . . .
C9 C 0.9989(5) 0.2312(4) 0.3301(3) 0.0169(8) Uani 1 1 d . U . . .
H9 H 1.071258 0.275432 0.305859 0.020 Uiso 1 1 calc R . . . .
C10 C 0.8576(5) 0.2701(3) 0.3645(3) 0.0125(6) Uani 1 1 d . U . . .
C11 C 0.8187(6) 0.3803(3) 0.3576(3) 0.0136(7) Uani 1 1 d . U . . .
C12 C 0.6627(5) 0.4178(3) 0.3450(2) 0.0126(6) Uani 1 1 d . U . . .
H12 H 0.651768 0.488051 0.349457 0.015 Uiso 1 1 calc R . . . .
C13 C 0.5083(6) 0.3598(3) 0.3248(3) 0.0122(7) Uani 1 1 d . U . . .
C14 C 0.9617(5) 0.4522(3) 0.3595(2) 0.0120(6) Uani 1 1 d . U . . .
C15 C 1.0984(5) 0.4406(3) 0.4200(3) 0.0162(7) Uani 1 1 d . U . . .
H15 H 1.100626 0.387500 0.459733 0.019 Uiso 1 1 calc R . . . .
C16 C 1.2317(5) 0.5076(3) 0.4220(3) 0.0172(7) Uani 1 1 d . U . . .
H16 H 1.321368 0.499755 0.463558 0.021 Uiso 1 1 calc R . . . .
C17 C 1.2315(5) 0.5857(3) 0.3622(3) 0.0169(7) Uani 1 1 d . U . . .
H17 H 1.321313 0.630074 0.363350 0.020 Uiso 1 1 calc R . . . .
C18 C 1.0968(6) 0.5977(4) 0.3006(3) 0.0175(8) Uani 1 1 d . U . . .
H18 H 1.096163 0.650156 0.260273 0.021 Uiso 1 1 calc R . . . .
C19 C 0.9637(5) 0.5316(3) 0.2993(3) 0.0158(7) Uani 1 1 d . U . . .
H19 H 0.873988 0.539930 0.257840 0.019 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 C3 2.162(4) . ?
O1 C1 1.460(6) . ?
O1 C2 1.325(5) . ?
O2 C2 1.210(5) . ?
O3 C4 1.464(5) . ?
O3 C13 1.364(5) . ?
O4 C13 1.206(6) . ?
C2 C3 1.513(6) . ?
C3 C4 1.529(5) . ?
C4 C5 1.501(6) . ?
C5 C6 1.391(6) . ?
C5 C10 1.424(6) . ?
C6 C7 1.387(7) . ?
C7 C8 1.380(7) . ?
C8 C9 1.391(6) . ?
C9 C10 1.403(6) . ?
C10 C11 1.482(6) . ?
C11 C12 1.352(7) . ?
C11 C14 1.492(6) . ?
C12 C13 1.470(6) . ?
C14 C15 1.390(6) . ?
C14 C19 1.400(6) . ?
C15 C16 1.389(6) . ?
C16 C17 1.383(6) . ?
C17 C18 1.390(7) . ?
C18 C19 1.382(6) . ?

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
C2 O1 C1 114.3(4) . . ?
C13 O3 C4 118.4(3) . . ?
O1 C2 C3 111.0(4) . . ?
O2 C2 O1 125.3(4) . . ?
O2 C2 C3 123.6(4) . . ?
C2 C3 I1 102.8(2) . . ?
C2 C3 C4 111.0(3) . . ?
C4 C3 I1 112.0(3) . . ?
O3 C4 C3 102.4(3) . . ?
O3 C4 C5 108.9(3) . . ?
C5 C4 C3 118.5(3) . . ?
C6 C5 C4 123.5(4) . . ?
C6 C5 C10 119.7(4) . . ?
C10 C5 C4 116.8(4) . . ?
C7 C6 C5 120.6(4) . . ?
C8 C7 C6 120.3(5) . . ?
C7 C8 C9 120.2(5) . . ?
C8 C9 C10 120.8(4) . . ?
C5 C10 C11 121.5(4) . . ?
C9 C10 C5 118.3(4) . . ?
C9 C10 C11 120.2(4) . . ?
C10 C11 C14 117.2(4) . . ?
C12 C11 C10 123.7(4) . . ?
C12 C11 C14 118.9(4) . . ?
C11 C12 C13 127.2(4) . . ?
O3 C13 C12 119.3(4) . . ?
O4 C13 O3 117.7(4) . . ?
O4 C13 C12 123.0(4) . . ?
C15 C14 C11 120.6(4) . . ?
C15 C14 C19 118.3(4) . . ?
C19 C14 C11 121.1(4) . . ?
C16 C15 C14 120.7(4) . . ?
C17 C16 C15 120.3(4) . . ?
C16 C17 C18 119.8(4) . . ?
C19 C18 C17 119.8(4) . . ?
C18 C19 C14 121.1(4) . . ?

_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 2.759
_oxdiff_exptl_absorpt_empirical_full_min 0.590
####################################################################### 
# 
# 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_tpt-9-7
_database_code_depnum_ccdc_archive 'CCDC 1944538'
loop_
_audit_author_name
_audit_author_address
'Panting '
;Hubei University
China
;
_audit_update_record             
;
2019-07-31 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_audit_creation_date             2019-06-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 I O5'
_chemical_formula_sum            'C19 H17 I O5'
_chemical_formula_weight         452.22
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8357(2)
_cell_length_b                   10.4353(3)
_cell_length_c                   10.4634(3)
_cell_angle_alpha                111.642(2)
_cell_angle_beta                 106.312(2)
_cell_angle_gamma                106.245(2)
_cell_volume                     865.10(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8993
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      30.0630
_cell_measurement_theta_min      2.3080
_shelx_estimated_absorpt_T_max   0.705
_shelx_estimated_absorpt_T_min   0.705
_exptl_absorpt_coefficient_mu    1.878
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13105
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.126
_diffrn_reflns_theta_min         2.320
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  31.00   0.50    0.53    --   10.30 -57.00 -30.00   68
  2  ω     -5.00  21.00   0.50    0.53    --   10.30 -99.00 -30.00   52
  3  ω    -14.00  30.00   0.50    0.53    --   -9.20 -99.00 -90.00   88
  4  ω     22.00  48.00   0.50    0.53    --   10.30-104.00-179.00   52
  5  ω    -17.00   9.00   0.50    0.53    --   -9.20 -99.00 -30.00   52
  6  ω    -26.00   6.00   0.50    0.53    --   -9.20 -99.00  60.00   64
  7  ω    -25.00  48.00   0.50    0.53    --   10.30 -99.00 120.00  146
  8  ω    -64.00 -31.00   0.50    0.53    --   10.30 -57.00 -30.00   66
  9  ω     -3.00  22.00   0.50    0.53    --   -9.20 -19.00 -30.00   50
 10  ω     38.00  64.00   0.50    0.53    --   -9.20  57.00-180.00   52
 11  ω    -23.00  10.00   0.50    0.53    --   -9.20  57.00-180.00   66
 12  ω    -85.00 -39.00   0.50    0.53    --   -9.20 -19.00 -30.00   92
 13  ω    -60.00 -25.00   0.50    0.53    --   10.30 -57.00   0.00   70
 14  ω    -64.00  29.00   0.50    0.53    --   10.30 -57.00-120.00  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0108288000
_diffrn_orient_matrix_UB_12      -0.0768852000
_diffrn_orient_matrix_UB_13      -0.0268588000
_diffrn_orient_matrix_UB_21      0.0352445000
_diffrn_orient_matrix_UB_22      0.0148909000
_diffrn_orient_matrix_UB_23      0.0761901000
_diffrn_orient_matrix_UB_31      -0.0745981000
_diffrn_orient_matrix_UB_32      -0.0206194000
_diffrn_orient_matrix_UB_33      0.0011126000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3978
_reflns_number_total             4297
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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         0.876
_refine_diff_density_min         -1.700
_refine_diff_density_rms         0.172
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0762
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_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 0.06883(2) 0.98040(2) 0.69995(2) 0.02044(7) Uani 1 1 d . . . . .
O1 O 0.6400(2) 0.9027(2) 0.8947(3) 0.0328(5) Uani 1 1 d . . . . .
O2 O 0.31100(18) 0.8014(2) 0.79732(19) 0.0201(4) Uani 1 1 d . . . . .
O3 O 0.1055(2) 0.7201(2) 0.8487(2) 0.0289(4) Uani 1 1 d . . . . .
O4 O 0.15049(18) 0.58791(18) 0.4886(2) 0.0165(3) Uani 1 1 d . . . . .
O5 O 0.2929(2) 0.4657(2) 0.4367(2) 0.0257(4) Uani 1 1 d . . . . .
C1 C 0.5437(3) 0.7701(3) 0.8876(3) 0.0281(6) Uani 1 1 d . . . . .
H1A H 0.604464 0.748494 0.960871 0.034 Uiso 1 1 calc R . . . .
H1B H 0.501892 0.683928 0.786772 0.034 Uiso 1 1 calc R . . . .
C2 C 0.7671(3) 0.8878(4) 0.8601(4) 0.0375(7) Uani 1 1 d . . . . .
H2A H 0.726884 0.813201 0.755170 0.056 Uiso 1 1 calc GR . . . .
H2B H 0.823197 0.855725 0.923861 0.056 Uiso 1 1 calc GR . . . .
H2C H 0.836757 0.984364 0.878158 0.056 Uiso 1 1 calc GR . . . .
C3 C 0.2588(3) 0.5685(3) 0.4364(3) 0.0177(5) Uani 1 1 d . . . . .
C4 C 0.4123(3) 0.7934(3) 0.9222(3) 0.0233(5) Uani 1 1 d . . . . .
H4A H 0.353821 0.709210 0.932926 0.028 Uiso 1 1 calc R . . . .
H4B H 0.453436 0.887230 1.016830 0.028 Uiso 1 1 calc R . . . .
C5 C 0.1606(3) 0.7575(3) 0.7723(3) 0.0174(5) Uani 1 1 d . . . . .
C6 C 0.0630(3) 0.7562(2) 0.6308(3) 0.0146(4) Uani 1 1 d . . . . .
H6 H -0.045543 0.680666 0.587805 0.018 Uiso 1 1 calc R . . . .
C7 C 0.1228(3) 0.7228(3) 0.5085(3) 0.0141(4) Uani 1 1 d . . . . .
H7 H 0.222762 0.809003 0.545536 0.017 Uiso 1 1 calc R . . . .
C8 C 0.0148(3) 0.6883(3) 0.3538(3) 0.0160(4) Uani 1 1 d . . . . .
C9 C -0.1448(3) 0.6471(3) 0.3063(3) 0.0199(5) Uani 1 1 d . . . . .
H9 H -0.189799 0.644584 0.373031 0.024 Uiso 1 1 calc R . . . .
C10 C -0.2381(3) 0.6095(3) 0.1579(3) 0.0238(5) Uani 1 1 d . . . . .
H10 H -0.345275 0.580918 0.125571 0.029 Uiso 1 1 calc R . . . .
C11 C -0.1707(3) 0.6147(3) 0.0591(3) 0.0240(5) Uani 1 1 d . . . . .
H11 H -0.232909 0.590231 -0.039291 0.029 Uiso 1 1 calc R . . . .
C12 C -0.0114(3) 0.6561(3) 0.1059(3) 0.0218(5) Uani 1 1 d . . . . .
H12 H 0.033183 0.660646 0.039335 0.026 Uiso 1 1 calc R . . . .
C13 C 0.0823(3) 0.6909(3) 0.2525(3) 0.0165(5) Uani 1 1 d . . . . .
C14 C 0.2538(3) 0.7310(3) 0.3020(3) 0.0185(5) Uani 1 1 d . . . . .
C15 C 0.3392(3) 0.8251(3) 0.2589(3) 0.0234(5) Uani 1 1 d . . . . .
H15 H 0.288293 0.860358 0.199888 0.028 Uiso 1 1 calc R . . . .
C16 C 0.4983(3) 0.8668(3) 0.3023(3) 0.0273(6) Uani 1 1 d . . . . .
H16 H 0.553685 0.932397 0.275431 0.033 Uiso 1 1 calc R . . . .
C17 C 0.5756(3) 0.8109(3) 0.3861(3) 0.0269(6) Uani 1 1 d . . . . .
H17 H 0.682549 0.839377 0.415737 0.032 Uiso 1 1 calc R . . . .
C18 C 0.4927(3) 0.7133(3) 0.4247(3) 0.0230(5) Uani 1 1 d . . . . .
H18 H 0.543188 0.672114 0.476481 0.028 Uiso 1 1 calc R . . . .
C19 C 0.3334(3) 0.6749(3) 0.3872(3) 0.0179(5) 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 C6 2.158(2) . ?
O1 C1 1.403(3) . ?
O1 C2 1.429(3) . ?
O2 C4 1.450(3) . ?
O2 C5 1.335(3) . ?
O3 C5 1.199(3) . ?
O4 C3 1.357(3) . ?
O4 C7 1.459(3) . ?
O5 C3 1.211(3) . ?
C1 C4 1.495(4) . ?
C3 C19 1.488(3) . ?
C5 C6 1.515(3) . ?
C6 C7 1.521(3) . ?
C7 C8 1.507(3) . ?
C8 C9 1.387(3) . ?
C8 C13 1.404(3) . ?
C9 C10 1.398(3) . ?
C10 C11 1.384(4) . ?
C11 C12 1.384(4) . ?
C12 C13 1.393(3) . ?
C13 C14 1.498(3) . ?
C14 C15 1.396(3) . ?
C14 C19 1.414(3) . ?
C15 C16 1.385(4) . ?
C16 C17 1.392(4) . ?
C17 C18 1.375(4) . ?
C18 C19 1.399(3) . ?

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 O1 C2 112.2(2) . . ?
C5 O2 C4 116.23(19) . . ?
C3 O4 C7 117.97(18) . . ?
O1 C1 C4 109.1(2) . . ?
O4 C3 C19 119.7(2) . . ?
O5 C3 O4 117.0(2) . . ?
O5 C3 C19 123.3(2) . . ?
O2 C4 C1 107.9(2) . . ?
O2 C5 C6 111.7(2) . . ?
O3 C5 O2 125.5(2) . . ?
O3 C5 C6 122.7(2) . . ?
C5 C6 I1 107.28(14) . . ?
C5 C6 C7 114.25(19) . . ?
C7 C6 I1 107.51(14) . . ?
O4 C7 C6 106.12(17) . . ?
O4 C7 C8 106.99(18) . . ?
C8 C7 C6 116.91(18) . . ?
C9 C8 C7 123.6(2) . . ?
C9 C8 C13 120.0(2) . . ?
C13 C8 C7 116.33(19) . . ?
C8 C9 C10 119.9(2) . . ?
C11 C10 C9 120.0(2) . . ?
C10 C11 C12 120.4(2) . . ?
C11 C12 C13 120.2(2) . . ?
C8 C13 C14 120.2(2) . . ?
C12 C13 C8 119.5(2) . . ?
C12 C13 C14 120.4(2) . . ?
C15 C14 C13 118.8(2) . . ?
C15 C14 C19 118.0(2) . . ?
C19 C14 C13 123.2(2) . . ?
C16 C15 C14 121.3(2) . . ?
C15 C16 C17 120.3(2) . . ?
C18 C17 C16 119.5(2) . . ?
C17 C18 C19 121.0(2) . . ?
C14 C19 C3 125.0(2) . . ?
C18 C19 C3 115.1(2) . . ?
C18 C19 C14 119.9(2) . . ?

_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 2.219
_oxdiff_exptl_absorpt_empirical_full_min 0.517
####################################################################### 
# 
# 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_tpt-14-10
_database_code_depnum_ccdc_archive 'CCDC 1973725'
loop_
_audit_author_name
_audit_author_address
'Panting '
;Hubei University
China
;
_audit_update_record             
;
2019-12-23 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_audit_creation_date             2019-06-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 F3 I O4'
_chemical_formula_sum            'C19 H14 F3 I O4'
_chemical_formula_weight         490.20
_chemical_absolute_configuration S
_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'
F F 0.0171 0.0103 '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'
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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   9.2645(2)
_cell_length_b                   22.2327(6)
_cell_length_c                   18.2492(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.504(3)
_cell_angle_gamma                90
_cell_volume                     3683.36(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14088
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      30.2730
_cell_measurement_theta_min      2.1370
_shelx_estimated_absorpt_T_max   0.716
_shelx_estimated_absorpt_T_min   0.716
_exptl_absorpt_coefficient_mu    1.790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28911
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.796
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.345
_diffrn_reflns_theta_min         2.157
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  84.00   0.50    3.06    --   10.14  57.00 -90.00  162
  2  ω    -12.00  81.00   0.50    3.06    --   10.14  57.00  90.00  186
  3  ω    -26.00  -1.00   0.50    3.06    --   -9.05 -99.00  30.00   50
  4  ω    -24.00  28.00   0.50    3.06    --   10.14 -99.00  90.00  104
  5  ω     33.00  59.00   0.50    3.06    --   10.14-143.00  89.00   52
  6  ω    -26.00  15.00   0.50    3.06    --   -9.05 -99.00 -90.00   82
  7  ω     11.00  54.00   0.50    3.06    --   10.14-127.00-100.00   86
  8  ω    -25.00  42.00   0.50    3.06    --   10.14 -99.00 -30.00  134
  9  ω    -24.00  46.00   0.50    3.06    --   10.14 -99.00 -60.00  140
 10  ω    -13.00  48.00   0.50    3.06    --   10.14 -99.00 120.00  122
 11  ω    -73.00 -31.00   0.50    3.06    --   -9.05 -57.00-180.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0606674000
_diffrn_orient_matrix_UB_12      0.0148044000
_diffrn_orient_matrix_UB_13      0.0226757000
_diffrn_orient_matrix_UB_21      0.0294529000
_diffrn_orient_matrix_UB_22      -0.0282118000
_diffrn_orient_matrix_UB_23      0.0136900000
_diffrn_orient_matrix_UB_31      0.0394532000
_diffrn_orient_matrix_UB_32      -0.0017124000
_diffrn_orient_matrix_UB_33      -0.0294997000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.711
_reflns_number_gt                7925
_reflns_number_total             8822
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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         2.060
_refine_diff_density_min         -1.779
_refine_diff_density_rms         0.147
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.09(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         8822
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.003
_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)+(0.0867P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1251
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.91(3)
 0.09(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C00O(H00O), C012(H012), C01A(H01A), C01C(H01H)
3.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00N(H00N), C00X(H00X), C00Z(H00Z), C013(H013), C014(H014),
 C015(H015), C016(H016), C018(H018), C019(H019), C01G(H01L), C01H(H01M)
3.c Idealised Me refined as rotating group:
 C00J(H00A,H00B,H00C), C01B(H01E,H01F,H01G), C01E(H01I,H01J,H01K), C01F(H01B,
 H01C,H01D)
;
_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
I001 I 0.90138(4) 0.56618(2) 0.42046(3) 0.02740(13) Uani 1 1 d . . . . .
I002 I 0.10057(4) 0.68812(2) 0.58028(3) 0.02725(13) Uani 1 1 d . . . . .
F003 F -0.0670(8) 0.6851(3) 0.2898(4) 0.0433(17) Uani 1 1 d . . . . .
O004 O 0.5421(7) 0.6936(2) 0.5394(4) 0.0259(13) Uani 1 1 d . . . . .
F005 F 0.1031(7) 0.6193(2) 0.2909(3) 0.0450(13) Uani 1 1 d . . . . .
O006 O 0.4613(7) 0.5581(2) 0.4599(4) 0.0248(12) Uani 1 1 d . . . . .
O007 O 0.4058(7) 0.5851(2) 0.6577(3) 0.0330(13) Uani 1 1 d . . . . .
F008 F 0.9005(7) 0.6242(3) 0.7107(3) 0.0490(14) Uani 1 1 d . . . . .
O009 O 0.7706(6) 0.7185(3) 0.5474(4) 0.0381(15) Uani 1 1 d . . . . .
F00A F 0.9237(11) 0.5514(4) 0.7877(3) 0.067(2) Uani 1 1 d . . . . .
F00B F 0.0765(10) 0.6922(3) 0.2114(4) 0.0541(19) Uani 1 1 d . . . . .
O00C O 0.5961(7) 0.6676(3) 0.3424(3) 0.0326(13) Uani 1 1 d . . . . .
O00D O 0.5495(9) 0.5722(3) 0.3067(4) 0.0428(18) Uani 1 1 d . . . . .
O00E O 0.4530(9) 0.6804(3) 0.6924(4) 0.0458(19) Uani 1 1 d . . . . .
C00F C 0.6932(12) 0.4374(4) 0.6279(6) 0.0313(19) Uani 1 1 d . . . . .
H00F H 0.668577 0.398716 0.640471 0.038 Uiso 1 1 calc R . . . .
O00G O 0.2308(7) 0.5302(3) 0.4521(4) 0.0351(13) Uani 1 1 d . . . . .
C00H C 0.0724(12) 0.6789(4) 0.2822(6) 0.034(2) Uani 1 1 d . . . . .
F00I F 1.0705(9) 0.5597(3) 0.7098(6) 0.067(3) Uani 1 1 d . . . . .
C00J C 0.5273(16) 0.6864(4) 0.2679(7) 0.042(3) Uani 1 1 d . . . . .
H00A H 0.596202 0.682210 0.235246 0.063 Uiso 1 1 calc GR . . . .
H00B H 0.497551 0.727680 0.268875 0.063 Uiso 1 1 calc GR . . . .
H00C H 0.442547 0.661747 0.249939 0.063 Uiso 1 1 calc GR . . . .
C00K C 0.5282(9) 0.4243(3) 0.5024(5) 0.0244(15) Uani 1 1 d . . . . .
C00L C 0.6327(9) 0.4603(3) 0.5563(4) 0.0235(15) Uani 1 1 d . . . . .
C00M C 0.4012(8) 0.4498(3) 0.4560(4) 0.0228(14) Uani 1 1 d . . . . .
C00N C 0.2299(8) 0.6950(3) 0.4081(5) 0.0234(15) Uani 1 1 d . . . . .
H00N H 0.202557 0.657172 0.422272 0.028 Uiso 1 1 calc R . . . .
C00O C 0.3910(8) 0.7120(3) 0.5377(4) 0.0208(13) Uani 1 1 d . . . . .
H00O H 0.391930 0.746811 0.570689 0.025 Uiso 1 1 calc R . . . .
C00P C 0.6774(8) 0.5172(3) 0.5380(4) 0.0232(14) Uani 1 1 d . . . . .
C00Q C 0.3246(8) 0.7308(3) 0.4590(4) 0.0217(14) Uani 1 1 d . . . . .
C00R C 0.3574(8) 0.5144(3) 0.4569(4) 0.0244(15) Uani 1 1 d . . . . .
C00S C 0.6033(9) 0.8010(3) 0.5363(5) 0.0246(15) Uani 1 1 d . . . . .
C00T C 0.4753(9) 0.8246(4) 0.4900(5) 0.0247(16) Uani 1 1 d . . . . .
C00U C 0.3692(8) 0.7874(3) 0.4376(4) 0.0256(16) Uani 1 1 d . . . . .
C00V C 0.6463(8) 0.7356(4) 0.5407(5) 0.0270(16) Uani 1 1 d . . . . .
C00W C 0.3304(9) 0.3515(4) 0.4010(5) 0.0304(17) Uani 1 1 d . . . . .
C00X C 0.3033(8) 0.4127(3) 0.4077(4) 0.0261(15) Uani 1 1 d . . . . .
H00X H 0.218080 0.429390 0.379291 0.031 Uiso 1 1 calc R . . . .
C00Y C 0.1765(9) 0.7161(4) 0.3363(5) 0.0302(17) Uani 1 1 d . . . . .
C00Z C 0.7874(11) 0.4710(4) 0.6791(5) 0.0364(19) Uani 1 1 d . . . . .
H00Z H 0.825419 0.455240 0.726197 0.044 Uiso 1 1 calc R . . . .
C010 C 0.6014(8) 0.6082(3) 0.3523(4) 0.0253(15) Uani 1 1 d . . . . .
C011 C 0.4007(9) 0.6439(3) 0.6469(4) 0.0254(15) Uani 1 1 d . . . . .
C012 C 0.6123(8) 0.5396(3) 0.4603(4) 0.0222(14) Uani 1 1 d . . . . .
H012 H 0.610137 0.506145 0.425127 0.027 Uiso 1 1 calc R . . . .
C013 C 0.7722(9) 0.5517(3) 0.5903(5) 0.0265(15) Uani 1 1 d . . . . .
H013 H 0.798858 0.590176 0.577886 0.032 Uiso 1 1 calc R . . . .
C014 C 0.4548(9) 0.8868(3) 0.4921(5) 0.0307(17) Uani 1 1 d . . . . .
H014 H 0.373547 0.903905 0.460787 0.037 Uiso 1 1 calc R . . . .
C015 C 0.7030(8) 0.8399(3) 0.5805(4) 0.0249(15) Uani 1 1 d . . . . .
H015 H 0.790020 0.824109 0.608204 0.030 Uiso 1 1 calc R . . . .
C016 C 0.5496(9) 0.3625(3) 0.4961(5) 0.0293(16) Uani 1 1 d . . . . .
H016 H 0.630714 0.344600 0.526527 0.035 Uiso 1 1 calc R . . . .
C017 C 0.6768(9) 0.9012(3) 0.5846(5) 0.0280(16) Uani 1 1 d . . . . .
C018 C 0.4543(11) 0.3273(4) 0.4463(6) 0.0343(19) Uani 1 1 d . . . . .
H018 H 0.473752 0.286417 0.443027 0.041 Uiso 1 1 calc R . . . .
C019 C 0.2175(9) 0.7732(4) 0.3150(5) 0.0316(17) Uani 1 1 d . . . . .
H019 H 0.178904 0.787662 0.267334 0.038 Uiso 1 1 calc R . . . .
C01A C 0.6841(8) 0.5935(3) 0.4307(4) 0.0218(14) Uani 1 1 d . . . . .
H01A H 0.687442 0.628211 0.463984 0.026 Uiso 1 1 calc R . . . .
C01B C 0.7817(12) 0.9411(4) 0.6374(6) 0.036(2) Uani 1 1 d . . . . .
H01E H 0.736951 0.952972 0.678267 0.054 Uiso 1 1 calc GR . . . .
H01F H 0.803835 0.976296 0.611114 0.054 Uiso 1 1 calc GR . . . .
H01G H 0.871070 0.919494 0.656286 0.054 Uiso 1 1 calc GR . . . .
C01C C 0.3164(8) 0.6598(3) 0.5692(4) 0.0238(15) Uani 1 1 d . . . . .
H01H H 0.309955 0.624847 0.536049 0.029 Uiso 1 1 calc R . . . .
C01D C 0.8266(10) 0.5286(4) 0.6611(5) 0.0318(17) Uani 1 1 d . . . . .
C01E C 0.4786(16) 0.5662(4) 0.7320(6) 0.041(3) Uani 1 1 d . . . . .
H01I H 0.478977 0.523036 0.734585 0.061 Uiso 1 1 calc GR . . . .
H01J H 0.426807 0.582165 0.768247 0.061 Uiso 1 1 calc GR . . . .
H01K H 0.578135 0.580730 0.742227 0.061 Uiso 1 1 calc GR . . . .
C01F C 0.2277(13) 0.3123(4) 0.3463(6) 0.041(2) Uani 1 1 d . . . . .
H01B H 0.132856 0.311077 0.359873 0.061 Uiso 1 1 calc GR . . . .
H01C H 0.267200 0.272297 0.347381 0.061 Uiso 1 1 calc GR . . . .
H01D H 0.217889 0.328577 0.296820 0.061 Uiso 1 1 calc GR . . . .
C01G C 0.5513(11) 0.9235(4) 0.5390(6) 0.0318(19) Uani 1 1 d . . . . .
H01L H 0.531353 0.964481 0.540049 0.038 Uiso 1 1 calc R . . . .
C01H C 0.3151(10) 0.8081(4) 0.3646(6) 0.0311(19) Uani 1 1 d . . . . .
H01M H 0.344879 0.845269 0.349579 0.037 Uiso 1 1 calc R . . . .
C01I C 0.9314(14) 0.5648(4) 0.7171(6) 0.038(3) 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
I001 C01A 2.146(8) . ?
I002 C01C 2.144(8) . ?
F003 C00H 1.334(13) . ?
O004 C00O 1.453(9) . ?
O004 C00V 1.340(10) . ?
F005 C00H 1.358(11) . ?
O006 C00R 1.361(9) . ?
O006 C012 1.456(9) . ?
O007 C011 1.321(9) . ?
O007 C01E 1.450(12) . ?
F008 C01I 1.352(11) . ?
O009 C00V 1.196(10) . ?
F00A C01I 1.338(13) . ?
F00B C00H 1.334(12) . ?
O00C C00J 1.445(12) . ?
O00C C010 1.331(9) . ?
O00D C010 1.186(10) . ?
O00E C011 1.194(10) . ?
C00F C00L 1.409(12) . ?
C00F C00Z 1.367(14) . ?
O00G C00R 1.211(9) . ?
C00H C00Y 1.485(13) . ?
F00I C01I 1.327(15) . ?
C00K C00L 1.472(11) . ?
C00K C00M 1.422(10) . ?
C00K C016 1.396(10) . ?
C00L C00P 1.392(10) . ?
C00M C00R 1.494(10) . ?
C00M C00X 1.400(10) . ?
C00N C00Q 1.393(11) . ?
C00N C00Y 1.387(12) . ?
C00O C00Q 1.504(10) . ?
C00O C01C 1.521(10) . ?
C00P C012 1.510(10) . ?
C00P C013 1.393(11) . ?
C00Q C00U 1.403(11) . ?
C00S C00T 1.413(11) . ?
C00S C00V 1.504(10) . ?
C00S C015 1.399(11) . ?
C00T C00U 1.481(11) . ?
C00T C014 1.397(11) . ?
C00U C01H 1.404(12) . ?
C00W C00X 1.395(11) . ?
C00W C018 1.383(13) . ?
C00W C01F 1.511(13) . ?
C00Y C019 1.402(13) . ?
C00Z C01D 1.387(13) . ?
C010 C01A 1.517(10) . ?
C011 C01C 1.517(11) . ?
C012 C01A 1.521(10) . ?
C013 C01D 1.389(12) . ?
C014 C01G 1.376(13) . ?
C015 C017 1.391(11) . ?
C016 C018 1.379(13) . ?
C017 C01B 1.512(12) . ?
C017 C01G 1.380(13) . ?
C019 C01H 1.382(13) . ?
C01D C01I 1.497(13) . ?

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
C00V O004 C00O 119.4(6) . . ?
C00R O006 C012 118.0(6) . . ?
C011 O007 C01E 115.1(6) . . ?
C010 O00C C00J 114.3(6) . . ?
C00Z C00F C00L 121.2(8) . . ?
F003 C00H F005 105.8(8) . . ?
F003 C00H F00B 107.0(9) . . ?
F003 C00H C00Y 112.9(8) . . ?
F005 C00H C00Y 111.9(8) . . ?
F00B C00H F005 106.4(8) . . ?
F00B C00H C00Y 112.4(9) . . ?
C00M C00K C00L 122.5(7) . . ?
C016 C00K C00L 120.3(7) . . ?
C016 C00K C00M 117.2(7) . . ?
C00F C00L C00K 120.7(7) . . ?
C00P C00L C00F 118.0(7) . . ?
C00P C00L C00K 121.3(7) . . ?
C00K C00M C00R 124.8(7) . . ?
C00X C00M C00K 119.8(7) . . ?
C00X C00M C00R 115.4(7) . . ?
C00Y C00N C00Q 119.7(7) . . ?
O004 C00O C00Q 108.0(6) . . ?
O004 C00O C01C 106.6(6) . . ?
C00Q C00O C01C 116.3(6) . . ?
C00L C00P C012 116.3(6) . . ?
C00L C00P C013 120.9(7) . . ?
C013 C00P C012 122.7(7) . . ?
C00N C00Q C00O 124.1(7) . . ?
C00N C00Q C00U 120.5(7) . . ?
C00U C00Q C00O 115.4(6) . . ?
O006 C00R C00M 119.7(6) . . ?
O00G C00R O006 117.6(7) . . ?
O00G C00R C00M 122.7(7) . . ?
C00T C00S C00V 125.0(7) . . ?
C015 C00S C00T 119.6(7) . . ?
C015 C00S C00V 115.4(7) . . ?
C00S C00T C00U 123.2(7) . . ?
C014 C00T C00S 117.1(8) . . ?
C014 C00T C00U 119.6(7) . . ?
C00Q C00U C00T 121.0(7) . . ?
C00Q C00U C01H 119.3(7) . . ?
C01H C00U C00T 119.7(7) . . ?
O004 C00V C00S 119.4(7) . . ?
O009 C00V O004 117.1(7) . . ?
O009 C00V C00S 123.5(7) . . ?
C00X C00W C01F 121.3(8) . . ?
C018 C00W C00X 118.1(8) . . ?
C018 C00W C01F 120.6(8) . . ?
C00W C00X C00M 121.6(7) . . ?
C00N C00Y C00H 120.1(8) . . ?
C00N C00Y C019 120.1(8) . . ?
C019 C00Y C00H 119.7(8) . . ?
C00F C00Z C01D 120.3(8) . . ?
O00C C010 C01A 109.8(6) . . ?
O00D C010 O00C 125.2(7) . . ?
O00D C010 C01A 124.9(7) . . ?
O007 C011 C01C 111.6(6) . . ?
O00E C011 O007 124.8(7) . . ?
O00E C011 C01C 123.6(7) . . ?
O006 C012 C00P 107.6(6) . . ?
O006 C012 C01A 105.2(6) . . ?
C00P C012 C01A 118.2(6) . . ?
C01D C013 C00P 119.7(7) . . ?
C01G C014 C00T 121.9(8) . . ?
C017 C015 C00S 122.4(7) . . ?
C018 C016 C00K 122.0(8) . . ?
C015 C017 C01B 120.8(8) . . ?
C01G C017 C015 117.1(7) . . ?
C01G C017 C01B 122.1(7) . . ?
C016 C018 C00W 121.3(8) . . ?
C01H C019 C00Y 120.3(8) . . ?
C010 C01A I001 106.6(5) . . ?
C010 C01A C012 109.4(6) . . ?
C012 C01A I001 107.0(5) . . ?
C00O C01C I002 108.3(5) . . ?
C011 C01C I002 107.2(5) . . ?
C011 C01C C00O 110.1(6) . . ?
C00Z C01D C013 119.9(8) . . ?
C00Z C01D C01I 119.9(8) . . ?
C013 C01D C01I 120.1(8) . . ?
C014 C01G C017 121.8(8) . . ?
C019 C01H C00U 120.0(8) . . ?
F008 C01I C01D 111.6(9) . . ?
F00A C01I F008 104.5(9) . . ?
F00A C01I C01D 112.7(8) . . ?
F00I C01I F008 105.6(8) . . ?
F00I C01I F00A 108.5(10) . . ?
F00I C01I C01D 113.3(9) . . ?

_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 2.361
_oxdiff_exptl_absorpt_empirical_full_min 0.463
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.91(3)
2 0.09(3)

####################################################################### 
# 
# 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_exp_2639
_database_code_depnum_ccdc_archive 'CCDC 1944537'
loop_
_audit_author_name
_audit_author_address
'Panting '
;Hubei University
China
;
_audit_update_record             
;
2019-07-31 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_audit_creation_date             2019-06-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 I O4'
_chemical_formula_sum            'C19 H17 I O4'
_chemical_formula_weight         436.22
_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'
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/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                   10.5655(4)
_cell_length_b                   14.9260(5)
_cell_length_c                   11.4963(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.437(4)
_cell_angle_gamma                90
_cell_volume                     1729.66(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7217
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      29.4440
_cell_measurement_theta_min      2.2890
_shelx_estimated_absorpt_T_max   0.706
_shelx_estimated_absorpt_T_min   0.706
_exptl_absorpt_coefficient_mu    1.871
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.816
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14543
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.305
_diffrn_reflns_theta_min         2.298
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.816
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  65.00   0.50    0.96    --   -9.20  78.00  -9.00  208
  2  ω    -40.00  14.00   0.50    0.96    --   -9.20 -57.00 150.00  108
  3  ω    -26.00  17.00   0.50    0.96    --   -9.20 -99.00  90.00   86
  4  ω    -12.00  17.00   0.50    0.96    --   -9.20 -99.00  30.00   58
  5  ω    -24.00  17.00   0.50    0.96    --   -9.20 -78.00-134.00   82
  6  ω    -26.00  13.00   0.50    0.96    --   -9.20 -99.00-180.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0581436000
_diffrn_orient_matrix_UB_12      0.0126480000
_diffrn_orient_matrix_UB_13      0.0146759000
_diffrn_orient_matrix_UB_21      -0.0333290000
_diffrn_orient_matrix_UB_22      -0.0382134000
_diffrn_orient_matrix_UB_23      -0.0312372000
_diffrn_orient_matrix_UB_31      0.0214378000
_diffrn_orient_matrix_UB_32      -0.0252714000
_diffrn_orient_matrix_UB_33      0.0546650000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3563
_reflns_number_total             4229
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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         0.901
_refine_diff_density_min         -1.305
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0394P)²+1.4639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0900
_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 Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C17(H17)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C16(H16A,H16B,H16C)
;
_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 0.78925(2) 0.63518(2) 0.12142(2) 0.02886(9) Uani 1 1 d . . . . .
O1 O 0.7216(2) 0.48742(13) 0.31772(19) 0.0279(5) Uani 1 1 d . . . . .
O2 O 0.6131(3) 0.42058(16) 0.1419(2) 0.0452(7) Uani 1 1 d . . . . .
O3 O 0.4659(2) 0.58936(12) 0.26954(18) 0.0213(4) Uani 1 1 d . . . . .
O4 O 0.3602(2) 0.56393(15) 0.4036(2) 0.0311(5) Uani 1 1 d . . . . .
C1 C 0.7681(4) 0.4007(2) 0.3704(3) 0.0322(7) Uani 1 1 d . . . . .
H1A H 0.824456 0.374652 0.327750 0.048 Uiso 1 1 calc GR . . . .
H1B H 0.693442 0.362160 0.363335 0.048 Uiso 1 1 calc GR . . . .
H1C H 0.817038 0.408050 0.454828 0.048 Uiso 1 1 calc GR . . . .
C2 C 0.6471(3) 0.48693(19) 0.2021(3) 0.0244(6) Uani 1 1 d . . . . .
C3 C 0.6119(3) 0.5796(2) 0.1513(3) 0.0248(6) Uani 1 1 d . . . . .
H3 H 0.541544 0.575736 0.073333 0.030 Uiso 1 1 calc R . . . .
C4 C 0.5680(3) 0.64169(17) 0.2367(3) 0.0202(6) Uani 1 1 d . . . . .
H4 H 0.642639 0.653318 0.309721 0.024 Uiso 1 1 calc R . . . .
C5 C 0.5056(3) 0.72903(18) 0.1831(3) 0.0193(6) Uani 1 1 d . . . . .
C6 C 0.4628(3) 0.7465(2) 0.0595(3) 0.0251(6) Uani 1 1 d . . . . .
H6 H 0.476614 0.704513 0.004829 0.030 Uiso 1 1 calc R . . . .
C7 C 0.3990(3) 0.8268(2) 0.0167(3) 0.0258(6) Uani 1 1 d . . . . .
H7 H 0.371527 0.839156 -0.066375 0.031 Uiso 1 1 calc R . . . .
C8 C 0.3767(3) 0.8880(2) 0.0984(3) 0.0261(6) Uani 1 1 d . . . . .
H8 H 0.332812 0.941209 0.069033 0.031 Uiso 1 1 calc R . . . .
C9 C 0.4181(3) 0.87243(18) 0.2235(3) 0.0214(6) Uani 1 1 d . . . . .
C10 C 0.3853(3) 0.9426(2) 0.3052(3) 0.0299(7) Uani 1 1 d . . . . .
H10A H 0.375911 0.914408 0.377225 0.045 Uiso 1 1 calc GR . . . .
H10B H 0.303677 0.971845 0.262344 0.045 Uiso 1 1 calc GR . . . .
H10C H 0.455383 0.986065 0.327808 0.045 Uiso 1 1 calc GR . . . .
C11 C 0.4849(3) 0.79183(17) 0.2669(2) 0.0172(5) Uani 1 1 d . . . . .
C12 C 0.5328(3) 0.77108(18) 0.3996(3) 0.0178(5) Uani 1 1 d . . . . .
C13 C 0.6020(3) 0.83480(19) 0.4827(3) 0.0216(6) Uani 1 1 d . . . . .
H13 H 0.624535 0.888663 0.453339 0.026 Uiso 1 1 calc R . . . .
C14 C 0.6387(3) 0.82115(19) 0.6072(3) 0.0246(6) Uani 1 1 d . . . . .
H14 H 0.685688 0.865329 0.659594 0.030 Uiso 1 1 calc R . . . .
C15 C 0.6056(3) 0.7412(2) 0.6552(3) 0.0237(6) Uani 1 1 d . . . . .
C16 C 0.6373(3) 0.7284(2) 0.7906(3) 0.0329(7) Uani 1 1 d . . . . .
H16A H 0.731399 0.732912 0.827981 0.049 Uiso 1 1 calc GR . . . .
H16B H 0.607466 0.670263 0.806926 0.049 Uiso 1 1 calc GR . . . .
H16C H 0.593250 0.773661 0.823457 0.049 Uiso 1 1 calc GR . . . .
C17 C 0.5428(3) 0.6750(2) 0.5743(3) 0.0215(6) Uani 1 1 d . . . . .
H17 H 0.523862 0.620451 0.604433 0.026 Uiso 1 1 calc R . . . .
C18 C 0.5070(3) 0.68842(18) 0.4480(3) 0.0179(5) Uani 1 1 d . . . . .
C19 C 0.4380(3) 0.61067(19) 0.3739(3) 0.0200(6) 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 C3 2.169(3) . ?
O1 C1 1.450(4) . ?
O1 C2 1.326(4) . ?
O2 C2 1.200(4) . ?
O3 C4 1.470(4) . ?
O3 C19 1.356(4) . ?
O4 C19 1.202(4) . ?
C2 C3 1.505(4) . ?
C3 C4 1.520(4) . ?
C4 C5 1.507(4) . ?
C5 C6 1.380(4) . ?
C5 C11 1.407(4) . ?
C6 C7 1.391(4) . ?
C7 C8 1.380(5) . ?
C8 C9 1.392(4) . ?
C9 C10 1.515(4) . ?
C9 C11 1.408(4) . ?
C11 C12 1.489(4) . ?
C12 C13 1.391(4) . ?
C12 C18 1.413(4) . ?
C13 C14 1.381(4) . ?
C14 C15 1.402(4) . ?
C15 C16 1.504(4) . ?
C15 C17 1.383(4) . ?
C17 C18 1.401(4) . ?
C18 C19 1.494(4) . ?

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
C2 O1 C1 116.0(2) . . ?
C19 O3 C4 118.3(2) . . ?
O1 C2 C3 112.8(2) . . ?
O2 C2 O1 124.6(3) . . ?
O2 C2 C3 122.6(3) . . ?
C2 C3 I1 106.7(2) . . ?
C2 C3 C4 113.4(3) . . ?
C4 C3 I1 108.35(19) . . ?
O3 C4 C3 103.4(2) . . ?
O3 C4 C5 107.5(2) . . ?
C5 C4 C3 116.4(2) . . ?
C6 C5 C4 123.6(3) . . ?
C6 C5 C11 120.5(3) . . ?
C11 C5 C4 115.8(2) . . ?
C5 C6 C7 120.1(3) . . ?
C8 C7 C6 119.6(3) . . ?
C7 C8 C9 121.8(3) . . ?
C8 C9 C10 117.7(3) . . ?
C8 C9 C11 118.5(3) . . ?
C11 C9 C10 123.7(3) . . ?
C5 C11 C9 119.4(3) . . ?
C5 C11 C12 119.2(2) . . ?
C9 C11 C12 121.4(2) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 C18 116.8(3) . . ?
C18 C12 C11 122.6(2) . . ?
C14 C13 C12 122.5(3) . . ?
C13 C14 C15 120.5(3) . . ?
C14 C15 C16 120.8(3) . . ?
C17 C15 C14 118.0(3) . . ?
C17 C15 C16 121.2(3) . . ?
C15 C17 C18 121.4(3) . . ?
C12 C18 C19 124.9(2) . . ?
C17 C18 C12 120.6(3) . . ?
C17 C18 C19 114.5(2) . . ?
O3 C19 C18 119.2(2) . . ?
O4 C19 O3 117.6(3) . . ?
O4 C19 C18 123.2(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 1.945
_oxdiff_exptl_absorpt_empirical_full_min 0.469
