# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20190828
_database_code_depnum_ccdc_archive 'CCDC 2052251'
loop_
_audit_author_name
_audit_author_address
'Norihiro tada'
;University
Japan
;
_audit_update_record             
;
2020-12-23 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 I O3'
_chemical_formula_sum            'C9 H7 I O3'
_chemical_formula_weight         290.05

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.4119(4)
_cell_length_b                   4.13820(10)
_cell_length_c                   18.5166(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.868(3)
_cell_angle_gamma                90
_cell_volume                     947.64(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2590
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      31.0

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.033
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.350
_shelx_estimated_absorpt_T_min   0.370
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.618
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Mercury CCD (2x2 bin mode)'
_diffrn_measurement_method       'profile data from φ-scans'
_diffrn_detector_area_resol_mean 14.6306
_diffrn_reflns_number            8188
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.903
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2173
_reflns_number_gt                1822
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0237P)²+0.1466P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2173
_refine_ls_number_parameters     124
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0508
_refine_ls_wR_factor_gt          0.0472
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.84070(2) 0.82022(4) 0.55329(2) 0.03734(8) Uani 1 1 d . . . . .
O1 O 0.91868(18) 0.6800(5) 0.44553(11) 0.0488(5) Uani 1 1 d . . . . .
O2 O 0.8977(2) 0.7730(6) 0.32655(12) 0.0556(6) Uani 1 1 d . . . . .
O3 O 0.9580(2) 0.7075(6) 0.69466(14) 0.0574(6) Uani 1 1 d D . . . .
H10 H 1.000(4) 0.867(9) 0.695(4) 0.069 Uiso 0.5 1 d D U P . .
H11 H 1.003(4) 0.554(10) 0.688(4) 0.069 Uiso 0.5 1 d D U P . .
C1 C 0.7310(2) 1.0017(6) 0.46855(14) 0.0352(6) Uani 1 1 d . . . . .
C2 C 0.7639(2) 0.9628(7) 0.39944(15) 0.0387(6) Uani 1 1 d . . . . .
C3 C 0.6964(3) 1.0810(8) 0.34127(16) 0.0470(7) Uani 1 1 d . . . . .
H3 H 0.7164 1.0587 0.2943 0.056 Uiso 1 1 calc R U . . .
C4 C 0.6009(3) 1.2297(8) 0.35304(19) 0.0550(9) Uani 1 1 d . . . . .
H4 H 0.5563 1.3077 0.3140 0.066 Uiso 1 1 calc R U . . .
C5 C 0.5704(3) 1.2645(8) 0.42291(19) 0.0521(8) Uani 1 1 d . . . . .
H5 H 0.5052 1.3653 0.4303 0.062 Uiso 1 1 calc R U . . .
C6 C 0.6357(2) 1.1510(7) 0.48193(17) 0.0441(7) Uani 1 1 d . . . . .
H6 H 0.6158 1.1749 0.5289 0.053 Uiso 1 1 calc R U . . .
C7 C 0.8675(3) 0.7942(7) 0.38847(16) 0.0424(7) Uani 1 1 d . . . . .
C8 C 0.7427(3) 0.9815(8) 0.62975(15) 0.0474(7) Uani 1 1 d . . . . .
C9 C 0.6925(3) 1.0627(10) 0.67642(18) 0.0619(9) Uani 1 1 d . . . . .
H9 H 0.6521 1.1279 0.7139 0.074 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C8 2.054(3) . ?
I1 C1 2.126(3) . ?
I1 O1 2.363(2) . ?
O1 C7 1.276(4) . ?
O2 C7 1.239(4) . ?
C1 C6 1.375(4) . ?
C1 C2 1.385(4) . ?
C2 C3 1.396(4) . ?
C2 C7 1.492(4) . ?
C3 C4 1.369(5) . ?
C4 C5 1.386(5) . ?
C5 C6 1.386(5) . ?
C8 C9 1.158(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
C8 I1 C1 90.82(11) . . ?
C8 I1 O1 166.07(10) . . ?
C1 I1 O1 75.29(9) . . ?
C7 O1 I1 113.42(19) . . ?
C6 C1 C2 123.0(3) . . ?
C6 C1 I1 122.2(2) . . ?
C2 C1 I1 114.8(2) . . ?
C1 C2 C3 117.9(3) . . ?
C1 C2 C7 120.3(3) . . ?
C3 C2 C7 121.8(3) . . ?
C4 C3 C2 120.4(3) . . ?
C3 C4 C5 120.3(3) . . ?
C4 C5 C6 120.8(3) . . ?
C1 C6 C5 117.7(3) . . ?
O2 C7 O1 124.9(3) . . ?
O2 C7 C2 119.4(3) . . ?
O1 C7 C2 115.8(3) . . ?
C9 C8 I1 175.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(4) . . . . ?
I1 C1 C2 C3 -179.0(2) . . . . ?
C6 C1 C2 C7 -179.1(3) . . . . ?
I1 C1 C2 C7 2.0(3) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C7 C2 C3 C4 178.9(3) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
I1 C1 C6 C5 179.2(2) . . . . ?
C4 C5 C6 C1 -0.4(5) . . . . ?
I1 O1 C7 O2 174.3(3) . . . . ?
I1 O1 C7 C2 -5.9(3) . . . . ?
C1 C2 C7 O2 -177.2(3) . . . . ?
C3 C2 C7 O2 3.9(4) . . . . ?
C1 C2 C7 O1 3.1(4) . . . . ?
C3 C2 C7 O1 -175.9(3) . . . . ?

_refine_diff_density_max         0.727
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_200915
_database_code_depnum_ccdc_archive 'CCDC 2052252'
loop_
_audit_author_name
_audit_author_address
'Norihiro tada'
;University
Japan
;
_audit_update_record             
;
2020-12-23 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 I N O4'
_chemical_formula_sum            'C23 H18 I N O4'
_chemical_formula_weight         499.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.9812(3)
_cell_length_b                   10.2319(3)
_cell_length_c                   22.2899(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.794(3)
_cell_angle_gamma                90
_cell_volume                     2033.94(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5779
_cell_measurement_theta_min      3.0199
_cell_measurement_theta_max      27.6706

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    1.604
_shelx_estimated_absorpt_T_min   0.400
_shelx_estimated_absorpt_T_max   0.690
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6509
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Mercury (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 14.7059
_diffrn_reflns_number            26961
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.840
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4676
_reflns_number_gt                4084
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²+0.5576P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4676
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.154
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.59468(2) 0.89041(2) 0.80121(2) 0.04781(7) Uani 1 1 d . . . . .
O1 O 0.5514(2) 0.69582(19) 0.73606(8) 0.0617(5) Uani 1 1 d . . . . .
O2 O 0.6759(2) 0.5249(2) 0.70641(10) 0.0713(6) Uani 1 1 d . . . . .
O3 O 0.70578(17) 0.81247(15) 0.93563(7) 0.0424(3) Uani 1 1 d . . . . .
O4 O 0.8282(3) 1.05449(18) 1.03947(8) 0.0638(5) Uani 1 1 d . . . . .
N1 N 0.7496(2) 0.9365(2) 0.95682(9) 0.0472(5) Uani 1 1 d . . . . .
C1 C 0.6673(3) 0.6279(3) 0.73502(12) 0.0519(6) Uani 1 1 d . . . . .
C2 C 0.8076(3) 0.6796(2) 0.77108(10) 0.0460(5) Uani 1 1 d . . . . .
C3 C 0.8064(3) 0.7960(2) 0.80324(10) 0.0438(5) Uani 1 1 d . . . . .
C4 C 0.9430(3) 0.6139(3) 0.77284(13) 0.0554(6) Uani 1 1 d . . . . .
H4 H 0.9466 0.5346 0.7527 0.067 Uiso 1 1 calc R U . . .
C5 C 1.0728(3) 0.6639(4) 0.80399(12) 0.0634(7) Uani 1 1 d . . . . .
H5 H 1.1628 0.6187 0.8045 0.076 Uiso 1 1 calc R U . . .
C6 C 1.0683(3) 0.7816(3) 0.83436(13) 0.0618(7) Uani 1 1 d . . . . .
H6 H 1.1559 0.8161 0.8547 0.074 Uiso 1 1 calc R U . . .
C7 C 0.9351(3) 0.8476(3) 0.83460(12) 0.0530(6) Uani 1 1 d . . . . .
H7 H 0.9316 0.9259 0.8556 0.064 Uiso 1 1 calc R U . . .
H7A H 0.737(3) 1.118(2) 0.9392(13) 0.047(7) Uiso 1 1 d . . . . .
C8 C 0.6678(3) 1.0435(2) 0.86064(12) 0.0539(6) Uani 1 1 d . . . . .
C9 C 0.7184(3) 1.0412(2) 0.91854(12) 0.0493(6) Uani 1 1 d . . . . .
C10 C 0.5607(3) 0.7821(2) 0.95386(12) 0.0527(6) Uani 1 1 d . . . . .
H10 H 0.4878 0.8471 0.9379 0.063 Uiso 1 1 calc R U . . .
H10A H 0.5661 0.7829 0.9976 0.063 Uiso 1 1 calc R U . . .
C11 C 0.5141(3) 0.6500(2) 0.93015(10) 0.0434(5) Uani 1 1 d . . . . .
C12 C 0.3782(3) 0.6021(3) 0.94309(15) 0.0646(8) Uani 1 1 d . . . . .
H12 H 0.3184 0.6519 0.9656 0.078 Uiso 1 1 calc R U . . .
C13 C 0.3308(4) 0.4804(3) 0.92270(15) 0.0775(10) Uani 1 1 d . . . . .
H13 H 0.2399 0.4479 0.9324 0.093 Uiso 1 1 calc R U . . .
H13A H 0.653(4) 1.125(3) 0.8422(15) 0.071(10) Uiso 1 1 d . . . . .
C14 C 0.4147(4) 0.4068(3) 0.88867(14) 0.0624(7) Uani 1 1 d . . . . .
H14 H 0.3811 0.3249 0.8749 0.075 Uiso 1 1 calc R U . . .
C15 C 0.5486(3) 0.4538(3) 0.87487(13) 0.0600(7) Uani 1 1 d . . . . .
H15 H 0.6061 0.4042 0.8513 0.072 Uiso 1 1 calc R U . . .
C16 C 0.5988(3) 0.5747(3) 0.89577(14) 0.0570(6) Uani 1 1 d . . . . .
H16 H 0.6908 0.6056 0.8866 0.068 Uiso 1 1 calc R U . . .
C17 C 0.8214(3) 0.9485(2) 1.01524(10) 0.0462(5) Uani 1 1 d . . . . .
C18 C 0.8940(2) 0.8304(2) 1.04456(10) 0.0426(5) Uani 1 1 d . . . . .
C19 C 0.9006(3) 0.8213(2) 1.10704(10) 0.0467(5) Uani 1 1 d . . . . .
H19 H 0.8508 0.8823 1.1283 0.056 Uiso 1 1 calc R U . . .
C20 C 0.9809(3) 0.7219(3) 1.13754(12) 0.0562(6) Uani 1 1 d . . . . .
H20 H 0.9834 0.7149 1.1792 0.067 Uiso 1 1 calc R U . . .
C21 C 1.0576(3) 0.6329(3) 1.10620(14) 0.0578(7) Uani 1 1 d . . . . .
H21 H 1.1123 0.5663 1.1269 0.069 Uiso 1 1 calc R U . . .
C22 C 1.0533(3) 0.6427(3) 1.04440(13) 0.0535(6) Uani 1 1 d . . . . .
H22 H 1.1063 0.5832 1.0236 0.064 Uiso 1 1 calc R U . . .
C23 C 0.9709(3) 0.7400(3) 1.01322(11) 0.0483(5) Uani 1 1 d . . . . .
H23 H 0.9667 0.7451 0.9714 0.058 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C8 2.106(2) . ?
I1 C3 2.128(2) . ?
I1 O1 2.4679(18) . ?
O1 C1 1.254(3) . ?
O2 C1 1.239(3) . ?
O3 N1 1.395(2) . ?
O3 C10 1.444(3) . ?
O4 C17 1.210(3) . ?
N1 C9 1.378(3) . ?
N1 C17 1.388(3) . ?
C1 C2 1.508(4) . ?
C2 C4 1.386(4) . ?
C2 C3 1.391(3) . ?
C3 C7 1.383(3) . ?
C4 C5 1.383(4) . ?
C5 C6 1.384(4) . ?
C6 C7 1.374(4) . ?
C8 C9 1.317(3) . ?
C10 C11 1.493(3) . ?
C11 C12 1.377(4) . ?
C11 C16 1.378(4) . ?
C12 C13 1.376(4) . ?
C13 C14 1.358(5) . ?
C14 C15 1.363(4) . ?
C15 C16 1.379(4) . ?
C17 C18 1.487(4) . ?
C18 C19 1.390(3) . ?
C18 C23 1.391(3) . ?
C19 C20 1.378(4) . ?
C20 C21 1.381(4) . ?
C21 C22 1.377(4) . ?
C22 C23 1.378(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
C8 I1 C3 96.48(10) . . ?
C8 I1 O1 170.41(9) . . ?
C3 I1 O1 74.01(8) . . ?
C1 O1 I1 112.63(16) . . ?
N1 O3 C10 109.17(17) . . ?
C9 N1 C17 123.4(2) . . ?
C9 N1 O3 117.98(18) . . ?
C17 N1 O3 118.63(19) . . ?
O2 C1 O1 125.7(3) . . ?
O2 C1 C2 118.3(3) . . ?
O1 C1 C2 116.0(2) . . ?
C4 C2 C3 117.4(2) . . ?
C4 C2 C1 121.3(2) . . ?
C3 C2 C1 121.2(2) . . ?
C7 C3 C2 122.0(2) . . ?
C7 C3 I1 121.95(19) . . ?
C2 C3 I1 116.03(17) . . ?
C5 C4 C2 121.3(3) . . ?
C4 C5 C6 119.7(3) . . ?
C7 C6 C5 120.3(3) . . ?
C6 C7 C3 119.1(3) . . ?
C9 C8 I1 130.5(2) . . ?
C8 C9 N1 130.0(2) . . ?
O3 C10 C11 108.64(19) . . ?
C12 C11 C16 118.6(2) . . ?
C12 C11 C10 117.8(2) . . ?
C16 C11 C10 123.6(2) . . ?
C13 C12 C11 120.0(3) . . ?
C14 C13 C12 121.1(3) . . ?
C13 C14 C15 119.5(3) . . ?
C14 C15 C16 120.2(3) . . ?
C11 C16 C15 120.6(2) . . ?
O4 C17 N1 119.4(2) . . ?
O4 C17 C18 122.4(2) . . ?
N1 C17 C18 118.1(2) . . ?
C19 C18 C23 119.6(2) . . ?
C19 C18 C17 117.4(2) . . ?
C23 C18 C17 122.5(2) . . ?
C20 C19 C18 120.1(2) . . ?
C19 C20 C21 120.0(3) . . ?
C22 C21 C20 120.1(3) . . ?
C21 C22 C23 120.4(3) . . ?
C22 C23 C18 119.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 O3 N1 C9 -94.3(3) . . . . ?
C10 O3 N1 C17 85.3(3) . . . . ?
I1 O1 C1 O2 179.3(2) . . . . ?
I1 O1 C1 C2 -2.0(3) . . . . ?
O2 C1 C2 C4 -0.4(4) . . . . ?
O1 C1 C2 C4 -179.2(2) . . . . ?
O2 C1 C2 C3 178.7(2) . . . . ?
O1 C1 C2 C3 -0.1(4) . . . . ?
C4 C2 C3 C7 1.8(4) . . . . ?
C1 C2 C3 C7 -177.4(2) . . . . ?
C4 C2 C3 I1 -178.31(18) . . . . ?
C1 C2 C3 I1 2.5(3) . . . . ?
C3 C2 C4 C5 -1.7(4) . . . . ?
C1 C2 C4 C5 177.4(2) . . . . ?
C2 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C7 1.2(4) . . . . ?
C5 C6 C7 C3 -1.1(4) . . . . ?
C2 C3 C7 C6 -0.4(4) . . . . ?
I1 C3 C7 C6 179.7(2) . . . . ?
I1 C8 C9 N1 5.6(5) . . . . ?
C17 N1 C9 C8 171.2(3) . . . . ?
O3 N1 C9 C8 -9.2(4) . . . . ?
N1 O3 C10 C11 179.18(19) . . . . ?
O3 C10 C11 C12 179.5(2) . . . . ?
O3 C10 C11 C16 -1.1(4) . . . . ?
C16 C11 C12 C13 1.1(5) . . . . ?
C10 C11 C12 C13 -179.4(3) . . . . ?
C11 C12 C13 C14 -1.4(6) . . . . ?
C12 C13 C14 C15 0.5(6) . . . . ?
C13 C14 C15 C16 0.5(5) . . . . ?
C12 C11 C16 C15 -0.1(4) . . . . ?
C10 C11 C16 C15 -179.5(3) . . . . ?
C14 C15 C16 C11 -0.8(5) . . . . ?
C9 N1 C17 O4 17.2(4) . . . . ?
O3 N1 C17 O4 -162.4(2) . . . . ?
C9 N1 C17 C18 -159.8(2) . . . . ?
O3 N1 C17 C18 20.6(3) . . . . ?
O4 C17 C18 C19 33.3(3) . . . . ?
N1 C17 C18 C19 -149.8(2) . . . . ?
O4 C17 C18 C23 -138.2(3) . . . . ?
N1 C17 C18 C23 38.7(3) . . . . ?
C23 C18 C19 C20 -1.0(3) . . . . ?
C17 C18 C19 C20 -172.8(2) . . . . ?
C18 C19 C20 C21 1.4(4) . . . . ?
C19 C20 C21 C22 -0.4(4) . . . . ?
C20 C21 C22 C23 -0.9(4) . . . . ?
C21 C22 C23 C18 1.3(4) . . . . ?
C19 C18 C23 C22 -0.3(3) . . . . ?
C17 C18 C23 C22 171.0(2) . . . . ?

_refine_diff_density_max         0.430
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.073

