# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_03-06-15_Alex
_database_code_depnum_ccdc_archive 'CCDC 1855606'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-20 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         'C12 H10 I O, Br'
_chemical_formula_sum            'C12 H10 Br I O'
_chemical_formula_weight         377.01

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   21.7877(8)
_cell_length_b                   5.8060(2)
_cell_length_c                   19.4890(14)
_cell_angle_alpha                90
_cell_angle_beta                 100.565(8)
_cell_angle_gamma                90
_cell_volume                     2423.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5334
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      68.4

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.067
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    24.390
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.251
_exptl_absorpt_process_details   
;
FS_PROCESS, CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_source_current           40.0
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 RX
_diffrn_measurement_device       
;
Crystal Goniometer
;
_diffrn_measurement_device_type  
;
Rigaku RAXIS conversion
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            6797
_diffrn_reflns_av_unetI/netI     0.0913
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.128
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_full        66.599
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2139
_reflns_number_gt                1679
_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 r12 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;

_computing_structure_solution    
;
Sir 2011, v1.0, Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., Giacovazzo, C., Mallamo, M., Mazzone, A., Polidori, G.
& Spagna, R. (2012). J. Appl. Cryst. 45, 357-361.

;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury 3.3 (Build RC5)
POV-Ray for Windows- version 3.7.0.msvc10.win64
;
_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)+(0.0501P)²+56.7444P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2139
_refine_ls_number_parameters     137
_refine_ls_number_restraints     89
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1786
_refine_ls_wR_factor_gt          0.1287
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_restrained_S_all      1.193
_refine_ls_shift/su_max          0.000
_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 0.17685(3) 0.51994(15) 0.43004(4) 0.0322(3) Uani 1 1 d . . . . .
C1 C 0.0793(6) 0.5097(14) 0.4158(6) 0.032(3) Uani 1 1 d D U . . .
C2 C 0.0491(4) 0.322(2) 0.4398(6) 0.035(3) Uani 1 1 d D U . . .
H2 H 0.0723 0.1971 0.4633 0.042 Uiso 1 1 calc R U . . .
C3 C -0.0161(4) 0.3213(18) 0.4285(5) 0.028(3) Uani 1 1 d D U . . .
H3 H -0.0379 0.1956 0.4438 0.033 Uiso 1 1 calc R U . . .
C4 C -0.0481(6) 0.5046(12) 0.3948(5) 0.030(3) Uani 1 1 d D U . . .
O1 O -0.1124(4) 0.5053(13) 0.3860(5) 0.044(2) Uani 1 1 d D U . . .
H1 H -0.1245 0.3839 0.4027 0.065 Uiso 1 1 calc R U . . .
C5 C -0.0190(4) 0.6908(19) 0.3715(6) 0.039(3) Uani 1 1 d D U . . .
H5 H -0.0428 0.8159 0.3493 0.047 Uiso 1 1 calc R U . . .
C6 C 0.0460(4) 0.694(2) 0.3808(6) 0.043(3) Uani 1 1 d D U . . .
H6 H 0.0672 0.8192 0.3639 0.052 Uiso 1 1 calc R U . . .
C7 C 0.1795(4) 0.2715(19) 0.3497(5) 0.029(3) Uani 1 1 d D U . . .
C8 C 0.2257(5) 0.104(2) 0.3594(5) 0.034(3) Uani 1 1 d D U . . .
H8 H 0.2571 0.1032 0.4003 0.040 Uiso 1 1 calc R U . . .
C9 C 0.2251(6) -0.058(2) 0.3088(6) 0.043(3) Uani 1 1 d D U . . .
H9 H 0.2563 -0.1746 0.3150 0.052 Uiso 1 1 calc R U . . .
C10 C 0.1797(4) -0.058(2) 0.2484(6) 0.035(3) Uani 1 1 d D U . . .
H10 H 0.1793 -0.1742 0.2139 0.041 Uiso 1 1 calc R U . . .
C11 C 0.1351(5) 0.115(2) 0.2399(5) 0.038(3) Uani 1 1 d D U . . .
H11 H 0.1046 0.1202 0.1983 0.046 Uiso 1 1 calc R U . . .
C12 C 0.1340(5) 0.2791(18) 0.2899(5) 0.033(3) Uani 1 1 d D U . . .
H12 H 0.1028 0.3953 0.2839 0.040 Uiso 1 1 calc R U . . .
Br1 Br -0.17087(5) 0.0747(3) 0.45439(7) 0.0366(4) 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 C1 2.094(13) . ?
I1 C7 2.137(11) . ?
C1 C2 1.400(11) . ?
C1 C6 1.400(11) . ?
C2 C3 1.395(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(10) . ?
C4 O1 1.379(15) . ?
O1 H1 0.8400 . ?
C5 C6 1.395(11) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.386(10) . ?
C7 C12 1.386(10) . ?
C8 C9 1.364(12) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.364(12) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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 I1 C7 92.7(4) . . ?
C2 C1 C6 121.9(12) . . ?
C2 C1 I1 120.4(7) . . ?
C6 C1 I1 117.7(7) . . ?
C3 C2 C1 118.3(9) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 119.3(9) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 122.9(11) . . ?
C3 C4 O1 118.6(6) . . ?
C5 C4 O1 118.5(6) . . ?
C4 O1 H1 109.5 . . ?
C4 C5 C6 119.3(9) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 118.3(9) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
C8 C7 C12 121.8(11) . . ?
C8 C7 I1 119.3(7) . . ?
C12 C7 I1 118.9(7) . . ?
C9 C8 C7 118.4(9) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 C10 121.6(9) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C9 C10 C11 118.3(12) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C12 C11 C10 121.6(9) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C7 118.4(8) . . ?
C11 C12 H12 120.8 . . ?
C7 C12 H12 120.8 . . ?

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 -0.3(18) . . . . ?
I1 C1 C2 C3 -179.3(8) . . . . ?
C1 C2 C3 C4 -0.5(17) . . . . ?
C2 C3 C4 C5 -0.1(18) . . . . ?
C2 C3 C4 O1 -177.9(10) . . . . ?
C3 C4 C5 C6 1.3(19) . . . . ?
O1 C4 C5 C6 179.2(11) . . . . ?
C4 C5 C6 C1 -2.0(18) . . . . ?
C2 C1 C6 C5 1.5(19) . . . . ?
I1 C1 C6 C5 -179.4(9) . . . . ?
C12 C7 C8 C9 -1.2(18) . . . . ?
I1 C7 C8 C9 177.3(9) . . . . ?
C7 C8 C9 C10 0(2) . . . . ?
C8 C9 C10 C11 1(2) . . . . ?
C9 C10 C11 C12 -1.9(19) . . . . ?
C10 C11 C12 C7 1.2(18) . . . . ?
C8 C7 C12 C11 0.4(18) . . . . ?
I1 C7 C12 C11 -178.0(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 Br1 0.84 2.37 3.205(8) 171.5 .

_refine_diff_density_max         1.371
_refine_diff_density_min         -2.144
_refine_diff_density_rms         0.304

####################################################################### 
# 
# 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_20171017-1
_database_code_depnum_ccdc_archive 'CCDC 1855608'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-20 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         'C10 H8 I O S, Br'
_chemical_formula_sum            'C10 H8 Br I O S'
_chemical_formula_weight         383.03

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   22.0476(15)
_cell_length_b                   5.6780(4)
_cell_length_c                   18.9405(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.965(7)
_cell_angle_gamma                90
_cell_volume                     2327.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9203
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.186
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    6.329
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.292
_exptl_absorpt_process_details   
;
FS_PROCESS, CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 RX
_diffrn_measurement_device       
;
Crystal Goniometer
;
_diffrn_measurement_device_type  
;
Rigaku RAXIS conversion
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            14785
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.149
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2663
_reflns_number_gt                1923
_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 r12 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;

_computing_structure_solution    
;
Sir 2011, v1.0, Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., Giacovazzo, C., Mallamo, M., Mazzone, A., Polidori, G.
& Spagna, R. (2012). J. Appl. Cryst. 45, 357-361.

;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury 3.3 (Build RC5)
POV-Ray for Windows- version 3.7.0.msvc10.win64
;
_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)+(0.0415P)²+31.8946P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2663
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.000
_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 0.17715(2) 0.01807(9) 0.42684(3) 0.03757(19) Uani 1 1 d . . . . .
S1 S 0.12883(11) -0.3061(6) 0.27859(15) 0.0639(7) Uani 1 1 d . . . . .
O1 O -0.1092(3) 0.0098(11) 0.3772(4) 0.0519(16) Uani 1 1 d . . . . .
H1O H -0.1232 -0.1158 0.3913 0.078 Uiso 1 1 calc R U . . .
C1 C 0.1843(4) -0.2557(15) 0.3526(4) 0.0395(18) Uani 1 1 d . . . . .
C2 C 0.2346(4) -0.4002(15) 0.3574(5) 0.0421(19) Uani 1 1 d . . . . .
H2 H 0.2700 -0.3967 0.3949 0.051 Uiso 1 1 calc R U . . .
C3 C 0.2259(5) -0.5535(17) 0.2988(5) 0.051(2) Uani 1 1 d . . . . .
H3 H 0.2560 -0.6666 0.2921 0.061 Uiso 1 1 calc R U . . .
C4 C 0.1723(5) -0.5305(18) 0.2527(5) 0.055(3) Uani 1 1 d . . . . .
H4 H 0.1599 -0.6254 0.2112 0.065 Uiso 1 1 calc R U . . .
C5 C 0.0799(4) 0.0045(14) 0.4095(5) 0.0377(18) Uani 1 1 d . . . . .
C6 C 0.0508(3) -0.1796(14) 0.4369(5) 0.0378(18) Uani 1 1 d . . . . .
H6 H 0.0742 -0.3017 0.4636 0.045 Uiso 1 1 calc R U . . .
C7 C -0.0127(4) -0.1829(15) 0.4250(5) 0.042(2) Uani 1 1 d . . . . .
H7 H -0.0335 -0.3105 0.4424 0.051 Uiso 1 1 calc R U . . .
C8 C -0.0463(4) -0.0024(15) 0.3878(5) 0.042(2) Uani 1 1 d . . . . .
C9 C -0.0157(4) 0.1807(16) 0.3625(6) 0.055(3) Uani 1 1 d . . . . .
H9 H -0.0391 0.3055 0.3373 0.066 Uiso 1 1 calc R U . . .
C10 C 0.0462(4) 0.1894(16) 0.3722(5) 0.050(2) Uani 1 1 d . . . . .
H10 H 0.0665 0.3173 0.3542 0.060 Uiso 1 1 calc R U . . .
Br1 Br 0.16993(4) 0.41348(16) 0.54388(5) 0.0432(2) 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 C5 2.108(8) . ?
I1 C1 2.122(8) . ?
S1 C1 1.700(8) . ?
S1 C4 1.721(10) . ?
O1 C8 1.365(9) . ?
O1 H1O 0.8400 . ?
C1 C2 1.369(11) . ?
C2 C3 1.395(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.334(13) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C6 1.379(11) . ?
C5 C10 1.398(11) . ?
C6 C7 1.375(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.377(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.374(12) . ?
C9 C10 1.344(11) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?

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
C5 I1 C1 94.1(3) . . ?
C1 S1 C4 90.4(5) . . ?
C8 O1 H1O 109.5 . . ?
C2 C1 S1 113.7(7) . . ?
C2 C1 I1 123.8(6) . . ?
S1 C1 I1 122.5(5) . . ?
C1 C2 C3 109.4(8) . . ?
C1 C2 H2 125.3 . . ?
C3 C2 H2 125.3 . . ?
C4 C3 C2 115.5(9) . . ?
C4 C3 H3 122.2 . . ?
C2 C3 H3 122.2 . . ?
C3 C4 S1 111.0(7) . . ?
C3 C4 H4 124.5 . . ?
S1 C4 H4 124.5 . . ?
C6 C5 C10 121.3(7) . . ?
C6 C5 I1 120.1(6) . . ?
C10 C5 I1 118.5(6) . . ?
C7 C6 C5 118.7(7) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C8 120.4(7) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
O1 C8 C9 117.6(8) . . ?
O1 C8 C7 123.1(8) . . ?
C9 C8 C7 119.2(7) . . ?
C10 C9 C8 122.3(8) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C5 118.0(8) . . ?
C9 C10 H10 121.0 . . ?
C5 C10 H10 121.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 S1 C1 C2 1.0(7) . . . . ?
C4 S1 C1 I1 178.0(5) . . . . ?
S1 C1 C2 C3 -0.3(10) . . . . ?
I1 C1 C2 C3 -177.3(6) . . . . ?
C1 C2 C3 C4 -0.8(12) . . . . ?
C2 C3 C4 S1 1.5(11) . . . . ?
C1 S1 C4 C3 -1.4(8) . . . . ?
C10 C5 C6 C7 2.1(13) . . . . ?
I1 C5 C6 C7 179.7(6) . . . . ?
C5 C6 C7 C8 -1.6(13) . . . . ?
C6 C7 C8 O1 -176.8(8) . . . . ?
C6 C7 C8 C9 0.3(14) . . . . ?
O1 C8 C9 C10 177.8(9) . . . . ?
C7 C8 C9 C10 0.6(15) . . . . ?
C8 C9 C10 C5 -0.2(16) . . . . ?
C6 C5 C10 C9 -1.2(14) . . . . ?
I1 C5 C10 C9 -178.9(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O Br1 0.84 2.43 3.250(7) 165.2 5_556

_refine_diff_density_max         1.208
_refine_diff_density_min         -1.821
_refine_diff_density_rms         0.207

####################################################################### 
# 
# 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_04282015-2
_database_code_depnum_ccdc_archive 'CCDC 1855611'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-20 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         'C24 H19 I2 O2, Br'
_chemical_formula_sum            ' C24 H19 Br I2 O2'
_chemical_formula_weight         673.09

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   11.0912(3)
_cell_length_b                   18.5647(13)
_cell_length_c                   10.9748(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2259.76(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    23158
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    4.569
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_process_details   
;
FS_Process, CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 RX
_diffrn_measurement_device_type  
;
Rigaku RAXIS conversion
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            28473
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.411
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2586
_reflns_number_gt                2404
_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 r15 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;

_computing_structure_solution    
;
SIR2004, J. Appl. Cryst. (2005). 38, 381-388.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury 3.3 (Build RC5)
POV-Ray for Windows- version 3.7.0.msvc10.win64
;
_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)+(0.0201P)²+2.3324P] 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         2586
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0183
_refine_ls_wR_factor_ref         0.0440
_refine_ls_wR_factor_gt          0.0432
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_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 0.63374(2) 0.08109(2) 0.08972(2) 0.02068(5) Uani 1 1 d . . . . .
O1 O 0.97839(15) 0.30688(8) -0.14167(14) 0.0260(3) Uani 1 1 d . . . . .
H1 H 0.730(2) 0.1197(14) -0.165(2) 0.031 Uiso 1 1 d . U . . .
C1 C 0.74417(19) 0.15975(11) 0.0076(2) 0.0214(4) Uani 1 1 d . . . . .
C2 C 0.7670(2) 0.15690(12) -0.1166(2) 0.0214(4) Uani 1 1 d . . . . .
H2 H 1.0000 0.302(2) -0.2500 0.062(14) Uiso 1 2 d S . P . .
C3 C 0.84708(19) 0.20610(11) -0.16636(19) 0.0201(4) Uani 1 1 d . . . . .
H3 H 0.8652 0.2037 -0.2509 0.024 Uiso 1 1 calc R U . . .
C4 C 0.9022(2) 0.25945(11) -0.09439(19) 0.0213(4) Uani 1 1 d . . . . .
C5 C 0.8747(2) 0.26188(12) 0.0310(2) 0.0242(4) Uani 1 1 d . . . . .
H5 H 0.9094 0.2982 0.0810 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7976(2) 0.21178(12) 0.08147(19) 0.0243(5) Uani 1 1 d . . . . .
H6 H 0.7810 0.2127 0.1664 0.029 Uiso 1 1 calc R U . . .
C7 C 0.75556(19) -0.00310(12) 0.05240(19) 0.0219(4) Uani 1 1 d . . . . .
C8 C 0.8567(2) -0.01130(15) 0.1242(2) 0.0359(6) Uani 1 1 d . . . . .
H8 H 0.8706 0.0193 0.1921 0.043 Uiso 1 1 calc R U . . .
C9 C 0.9377(3) -0.06541(17) 0.0945(2) 0.0453(7) Uani 1 1 d . . . . .
H9 H 1.0086 -0.0716 0.1419 0.054 Uiso 1 1 calc R U . . .
C10 C 0.9161(2) -0.11018(14) -0.0030(2) 0.0357(6) Uani 1 1 d . . . . .
H10 H 0.9721 -0.1472 -0.0225 0.043 Uiso 1 1 calc R U . . .
C11 C 0.8140(2) -0.10172(13) -0.0724(2) 0.0326(5) Uani 1 1 d . . . . .
H11 H 0.7991 -0.1334 -0.1387 0.039 Uiso 1 1 calc R U . . .
C12 C 0.7319(2) -0.04687(12) -0.0459(2) 0.0284(5) Uani 1 1 d . . . . .
H12 H 0.6619 -0.0400 -0.0944 0.034 Uiso 1 1 calc R U . . .
Br1 Br 0.5000 -0.04690(2) 0.2500 0.02279(7) Uani 1 2 d S T P . .


_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 C7 2.106(2) . ?
I1 C1 2.108(2) . ?
O1 C4 1.326(3) . ?
O1 H2 1.216(4) . ?
C1 C2 1.387(3) . ?
C1 C6 1.394(3) . ?
C2 C3 1.386(3) . ?
C2 H1 0.96(3) . ?
C3 C4 1.406(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.411(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.376(3) . ?
C7 C8 1.380(3) . ?
C8 C9 1.386(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.373(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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
C7 I1 C1 93.33(8) . . ?
C4 O1 H2 117.5(17) . . ?
C2 C1 C6 121.4(2) . . ?
C2 C1 I1 119.97(16) . . ?
C6 C1 I1 118.57(15) . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 H1 121.9(16) . . ?
C1 C2 H1 119.5(16) . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
O1 C4 C3 121.64(18) . . ?
O1 C4 C5 119.89(19) . . ?
C3 C4 C5 118.5(2) . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.83(19) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C12 C7 C8 122.5(2) . . ?
C12 C7 I1 117.94(16) . . ?
C8 C7 I1 119.52(17) . . ?
C7 C8 C9 118.2(2) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 118.0(2) . . ?
C7 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.6(3) . . . . ?
I1 C1 C2 C3 -175.22(15) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?
C2 C3 C4 O1 -179.65(19) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
O1 C4 C5 C6 -178.6(2) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C4 C5 C6 C1 -1.7(3) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
I1 C1 C6 C5 177.02(16) . . . . ?
C12 C7 C8 C9 0.6(4) . . . . ?
I1 C7 C8 C9 -177.5(2) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C8 C7 C12 C11 0.4(4) . . . . ?
I1 C7 C12 C11 178.63(18) . . . . ?
C10 C11 C12 C7 -1.3(4) . . . . ?

_refine_diff_density_max         1.323
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.109


# start Validation Reply Form
_vrf_PLAT094_04282015-2          
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.48 Report
RESPONSE: Large e- denisty peaks are located near the I atom. Small peaks are 
located in the aromatic rings.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_10252014-4
_database_code_depnum_ccdc_archive 'CCDC 1855610'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-20 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         'C13 H9 I O3'
_chemical_formula_sum            'C13 H9 I O3'
_chemical_formula_weight         340.10

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           171
_space_group_name_H-M_alt        'P 62'
_space_group_name_Hall           'P 62'

_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, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'x-y, x, z+1/3'
'y, -x+y, z+2/3'

_cell_length_a                   15.5268(11)
_cell_length_b                   15.5268(11)
_cell_length_c                   16.7336(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3493.7(6)
_cell_formula_units_Z            12
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    7977
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.940
_exptl_crystal_F_000             1968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    2.742
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.029
_exptl_absorpt_process_details   
;
FS_PROCESS, CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 RX
_diffrn_measurement_device       
;
Crystal Goniometer
;
_diffrn_measurement_device_type  
;
Rigaku RAXIS conversion
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            9921
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.030
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             5056
_reflns_number_gt                4462
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_max     0.890
_reflns_Friedel_fraction_full    0.904

_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 r12 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;

_computing_structure_solution    
;
Sir 2011, v1.0, Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., Giacovazzo, C., Mallamo, M., Mazzone, A., Polidori, G.
& Spagna, R. (2012). J. Appl. Cryst. 45, 357-361.

;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury 3.3 (Build RC5)
POV-Ray for Windows- version 3.7.0.msvc10.win64
;
_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)+(0.0190P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1676 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.039(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5056
_refine_ls_number_parameters     309
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0681
_refine_ls_wR_factor_gt          0.0647
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_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 0.88331(4) 0.10484(4) 0.05922(3) 0.01903(12) Uani 1 1 d . . . . .
O1 O 0.9172(4) 0.1338(4) 0.2049(3) 0.0234(13) Uani 1 1 d . . . . .
O2 O 0.8340(4) 0.0831(4) 0.3201(3) 0.0241(13) Uani 1 1 d . . . . .
O3 O 0.7541(5) -0.0044(4) -0.2939(3) 0.0267(14) Uani 1 1 d . . . . .
H3O H 0.7546 -0.0560 -0.3081 0.040 Uiso 1 1 calc R U . . .
C1 C 0.7420(5) 0.0286(5) 0.1154(4) 0.0149(16) Uani 1 1 d . . . . .
C2 C 0.6566(6) -0.0188(6) 0.0712(5) 0.0217(17) Uani 1 1 d . . . . .
H2 H 0.6593 -0.0216 0.0146 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5665(6) -0.0626(6) 0.1107(5) 0.0229(18) Uani 1 1 d . . . . .
H3 H 0.5064 -0.0959 0.0811 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5634(6) -0.0582(6) 0.1926(5) 0.0210(18) Uani 1 1 d . . . . .
H4 H 0.5009 -0.0875 0.2190 0.025 Uiso 1 1 calc R U . . .
C5 C 0.6505(5) -0.0115(5) 0.2372(4) 0.0170(16) Uani 1 1 d . . . . .
H5 H 0.6474 -0.0106 0.2939 0.020 Uiso 1 1 calc R U . . .
C6 C 0.7425(6) 0.0342(5) 0.1987(4) 0.0150(16) Uani 1 1 d . . . . .
C7 C 0.8378(6) 0.0875(5) 0.2446(4) 0.0174(17) Uani 1 1 d . . . . .
C8 C 0.8308(6) 0.0607(5) -0.0577(4) 0.0162(16) Uani 1 1 d . . . . .
C9 C 0.7985(6) 0.1148(5) -0.1010(4) 0.0187(16) Uani 1 1 d . . . . .
H9 H 0.7945 0.1678 -0.0765 0.022 Uiso 1 1 calc R U . . .
C10 C 0.7718(6) 0.0912(6) -0.1806(4) 0.0188(17) Uani 1 1 d . . . . .
H10 H 0.7483 0.1272 -0.2107 0.023 Uiso 1 1 calc R U . . .
C11 C 0.7800(6) 0.0142(6) -0.2157(5) 0.0195(17) Uani 1 1 d . . . . .
C12 C 0.8105(6) -0.0414(6) -0.1716(5) 0.0253(19) Uani 1 1 d . . . . .
H12 H 0.8130 -0.0956 -0.1956 0.030 Uiso 1 1 calc R U . . .
C13 C 0.8375(6) -0.0171(6) -0.0920(5) 0.0253(19) Uani 1 1 d . . . . .
H13 H 0.8603 -0.0533 -0.0614 0.030 Uiso 1 1 calc R U . . .
I1A I 0.30108(4) -0.48582(4) -0.04655(3) 0.02415(14) Uani 1 1 d . . . . .
O1A O 0.2508(4) -0.5190(4) -0.1887(3) 0.0312(15) Uani 1 1 d . . . . .
O2A O 0.3201(4) -0.4760(4) -0.3098(3) 0.0251(14) Uani 1 1 d . . . . .
O3A O 0.4496(5) -0.3785(4) 0.3050(3) 0.0270(14) Uani 1 1 d . . . . .
H3OA H 0.4679 -0.3189 0.3157 0.041 Uiso 1 1 calc R U . . .
C1A C 0.4359(5) -0.4163(5) -0.1132(4) 0.0184(16) Uani 1 1 d . . . . .
C2A C 0.5258(6) -0.3663(6) -0.0746(4) 0.0207(17) Uani 1 1 d . . . . .
H2A H 0.5291 -0.3638 -0.0179 0.025 Uiso 1 1 calc R U . . .
C3A C 0.6118(6) -0.3194(6) -0.1203(5) 0.0242(19) Uani 1 1 d . . . . .
H3A H 0.6749 -0.2822 -0.0954 0.029 Uiso 1 1 calc R U . . .
C4A C 0.6044(6) -0.3274(6) -0.2030(5) 0.0226(18) Uani 1 1 d . . . . .
H4A H 0.6630 -0.2961 -0.2346 0.027 Uiso 1 1 calc R U . . .
C5A C 0.5132(6) -0.3801(6) -0.2397(4) 0.0208(17) Uani 1 1 d . . . . .
H5A H 0.5103 -0.3855 -0.2963 0.025 Uiso 1 1 calc R U . . .
C6A C 0.4251(6) -0.4258(5) -0.1961(4) 0.0181(17) Uani 1 1 d . . . . .
C7A C 0.3249(6) -0.4785(6) -0.2354(5) 0.0225(19) Uani 1 1 d . . . . .
C8A C 0.3647(5) -0.4429(6) 0.0684(4) 0.0198(17) Uani 1 1 d . U . . .
C9A C 0.3652(6) -0.5146(6) 0.1182(5) 0.0291(19) Uani 1 1 d . U . . .
H9A H 0.3457 -0.5792 0.0984 0.035 Uiso 1 1 calc R U . . .
C10A C 0.3946(7) -0.4901(6) 0.1969(4) 0.0272(19) Uani 1 1 d . U . . .
H10A H 0.3961 -0.5383 0.2309 0.033 Uiso 1 1 calc R U . . .
C11A C 0.4220(5) -0.3967(6) 0.2271(5) 0.0192(16) Uani 1 1 d . U . . .
C12A C 0.4215(5) -0.3251(6) 0.1763(4) 0.0198(16) Uani 1 1 d . U . . .
H12A H 0.4412 -0.2605 0.1962 0.024 Uiso 1 1 calc R U . . .
C13A C 0.3925(6) -0.3480(6) 0.0978(4) 0.0200(17) Uani 1 1 d . U . . .
H13A H 0.3913 -0.2997 0.0637 0.024 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 2.098(7) . ?
I1 C1 2.122(7) . ?
I1 O1 2.486(5) . ?
O1 C7 1.262(9) . ?
O2 C7 1.265(8) . ?
O3 C11 1.357(9) . ?
O3 H3O 0.8400 . ?
C1 C2 1.368(10) . ?
C1 C6 1.396(10) . ?
C2 C3 1.380(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.496(10) . ?
C8 C9 1.380(10) . ?
C8 C13 1.387(10) . ?
C9 C10 1.387(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.395(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(11) . ?
C12 C13 1.391(11) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
I1A C8A 2.112(7) . ?
I1A C1A 2.129(7) . ?
I1A O1A 2.476(5) . ?
O1A C7A 1.268(10) . ?
O2A C7A 1.250(9) . ?
O3A C11A 1.356(9) . ?
O3A H3OA 0.8400 . ?
C1A C2A 1.373(11) . ?
C1A C6A 1.397(10) . ?
C2A C3A 1.387(11) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.388(10) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.376(11) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.392(10) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.498(11) . ?
C8A C9A 1.393(11) . ?
C8A C13A 1.402(11) . ?
C9A C10A 1.384(11) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.386(11) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.403(10) . ?
C12A C13A 1.376(10) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?

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 96.1(3) . . ?
C8 I1 O1 170.2(2) . . ?
C1 I1 O1 74.5(2) . . ?
C7 O1 I1 110.8(5) . . ?
C11 O3 H3O 109.5 . . ?
C2 C1 C6 123.2(7) . . ?
C2 C1 I1 120.9(5) . . ?
C6 C1 I1 115.9(5) . . ?
C1 C2 C3 118.5(7) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 120.4(7) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.8(7) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 119.9(7) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 117.2(7) . . ?
C5 C6 C7 121.5(6) . . ?
C1 C6 C7 121.3(7) . . ?
O1 C7 O2 124.2(7) . . ?
O1 C7 C6 117.3(6) . . ?
O2 C7 C6 118.5(7) . . ?
C9 C8 C13 121.4(7) . . ?
C9 C8 I1 119.5(5) . . ?
C13 C8 I1 118.9(5) . . ?
C8 C9 C10 119.7(7) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 119.1(7) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
O3 C11 C12 122.5(7) . . ?
O3 C11 C10 116.4(7) . . ?
C12 C11 C10 121.1(7) . . ?
C11 C12 C13 119.4(7) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C8 C13 C12 119.3(7) . . ?
C8 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C8A I1A C1A 97.5(3) . . ?
C8A I1A O1A 171.7(2) . . ?
C1A I1A O1A 74.4(3) . . ?
C7A O1A I1A 112.0(5) . . ?
C11A O3A H3OA 109.5 . . ?
C2A C1A C6A 124.2(7) . . ?
C2A C1A I1A 120.3(5) . . ?
C6A C1A I1A 115.5(5) . . ?
C1A C2A C3A 118.5(7) . . ?
C1A C2A H2A 120.8 . . ?
C3A C2A H2A 120.8 . . ?
C2A C3A C4A 119.2(8) . . ?
C2A C3A H3A 120.4 . . ?
C4A C3A H3A 120.4 . . ?
C5A C4A C3A 120.8(8) . . ?
C5A C4A H4A 119.6 . . ?
C3A C4A H4A 119.6 . . ?
C4A C5A C6A 121.8(7) . . ?
C4A C5A H5A 119.1 . . ?
C6A C5A H5A 119.1 . . ?
C5A C6A C1A 115.5(7) . . ?
C5A C6A C7A 122.4(7) . . ?
C1A C6A C7A 122.0(7) . . ?
O2A C7A O1A 125.1(8) . . ?
O2A C7A C6A 118.8(8) . . ?
O1A C7A C6A 116.0(7) . . ?
C9A C8A C13A 120.6(7) . . ?
C9A C8A I1A 118.7(6) . . ?
C13A C8A I1A 120.1(6) . . ?
C10A C9A C8A 118.8(8) . . ?
C10A C9A H9A 120.6 . . ?
C8A C9A H9A 120.6 . . ?
C9A C10A C11A 121.4(8) . . ?
C9A C10A H10A 119.3 . . ?
C11A C10A H10A 119.3 . . ?
O3A C11A C10A 118.0(7) . . ?
O3A C11A C12A 122.8(7) . . ?
C10A C11A C12A 119.2(7) . . ?
C13A C12A C11A 120.2(7) . . ?
C13A C12A H12A 119.9 . . ?
C11A C12A H12A 119.9 . . ?
C12A C13A C8A 119.7(7) . . ?
C12A C13A H13A 120.1 . . ?
C8A C13A H13A 120.1 . . ?

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 0.6(12) . . . . ?
I1 C1 C2 C3 -176.5(6) . . . . ?
C1 C2 C3 C4 0.0(12) . . . . ?
C2 C3 C4 C5 -1.2(12) . . . . ?
C3 C4 C5 C6 1.8(11) . . . . ?
C4 C5 C6 C1 -1.2(10) . . . . ?
C4 C5 C6 C7 178.4(7) . . . . ?
C2 C1 C6 C5 0.0(11) . . . . ?
I1 C1 C6 C5 177.2(5) . . . . ?
C2 C1 C6 C7 -179.6(7) . . . . ?
I1 C1 C6 C7 -2.3(9) . . . . ?
I1 O1 C7 O2 174.6(6) . . . . ?
I1 O1 C7 C6 -4.9(8) . . . . ?
C5 C6 C7 O1 -174.2(7) . . . . ?
C1 C6 C7 O1 5.3(11) . . . . ?
C5 C6 C7 O2 6.3(11) . . . . ?
C1 C6 C7 O2 -174.2(7) . . . . ?
C13 C8 C9 C10 0.1(12) . . . . ?
I1 C8 C9 C10 174.4(5) . . . . ?
C8 C9 C10 C11 -1.1(11) . . . . ?
C9 C10 C11 O3 -179.1(7) . . . . ?
C9 C10 C11 C12 2.5(12) . . . . ?
O3 C11 C12 C13 179.0(8) . . . . ?
C10 C11 C12 C13 -2.8(13) . . . . ?
C9 C8 C13 C12 -0.3(12) . . . . ?
I1 C8 C13 C12 -174.7(6) . . . . ?
C11 C12 C13 C8 1.7(13) . . . . ?
C6A C1A C2A C3A 1.9(12) . . . . ?
I1A C1A C2A C3A -178.0(6) . . . . ?
C1A C2A C3A C4A -2.2(12) . . . . ?
C2A C3A C4A C5A 0.7(13) . . . . ?
C3A C4A C5A C6A 1.2(13) . . . . ?
C4A C5A C6A C1A -1.5(11) . . . . ?
C4A C5A C6A C7A 176.4(7) . . . . ?
C2A C1A C6A C5A -0.1(12) . . . . ?
I1A C1A C6A C5A 179.8(5) . . . . ?
C2A C1A C6A C7A -178.0(7) . . . . ?
I1A C1A C6A C7A 2.0(10) . . . . ?
I1A O1A C7A O2A -173.3(7) . . . . ?
I1A O1A C7A C6A 3.6(9) . . . . ?
C5A C6A C7A O2A -4.6(12) . . . . ?
C1A C6A C7A O2A 173.1(8) . . . . ?
C5A C6A C7A O1A 178.3(7) . . . . ?
C1A C6A C7A O1A -4.0(11) . . . . ?
C13A C8A C9A C10A -0.7(12) . . . . ?
I1A C8A C9A C10A -171.6(6) . . . . ?
C8A C9A C10A C11A 0.9(13) . . . . ?
C9A C10A C11A O3A 179.7(7) . . . . ?
C9A C10A C11A C12A -1.1(12) . . . . ?
O3A C11A C12A C13A -179.8(7) . . . . ?
C10A C11A C12A C13A 1.1(11) . . . . ?
C11A C12A C13A C8A -0.9(11) . . . . ?
C9A C8A C13A C12A 0.7(12) . . . . ?
I1A C8A C13A C12A 171.4(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3O O2 0.84 1.80 2.636(8) 175.0 5_544
O3A H3OA O2A 0.84 1.86 2.675(8) 163.7 3_545

_refine_diff_density_max         1.462
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.129

####################################################################### 
# 
# 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_20180205-1
_database_code_depnum_ccdc_archive 'CCDC 1855609'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-20 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         'C10 H8 I O S, C F3 O3 S'
_chemical_formula_sum            'C11 H8 F3 I O4 S2'
_chemical_formula_weight         452.19

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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 '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'

_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                   12.296(3)
_cell_length_b                   10.711(2)
_cell_length_c                   12.599(2)
_cell_angle_alpha                90
_cell_angle_beta                 115.117(8)
_cell_angle_gamma                90
_cell_volume                     1502.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9954
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.999
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    2.452
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_process_details   
;
FS_PROCESS, CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 RX
_diffrn_measurement_device       
;
Crystal Goniometer
;
_diffrn_measurement_device_type  
;
Rigaku RAXIS conversion
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            18294
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.249
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3439
_reflns_number_gt                2897
_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 r12 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_structure_solution    
;
Sir 2004, release 1.00, M. C. Burla, R. Caliandro, M. Camalli,
B. Carrozzini, G. L. Cascarano, L. De Caro, C. Giacovazzo,
G. Polidori & R. Spagna, J. Appl. Cryst. (2005). 38, 381-388.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury 3.3 (Build RC5)
POV-Ray for Windows- version 3.7.0.msvc10.win64
;
_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)+(0.0145P)²+1.4239P] 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         3439
_refine_ls_number_parameters     210
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0552
_refine_ls_wR_factor_gt          0.0499
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_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 0.64340(2) 0.02491(2) 0.72807(2) 0.02784(7) Uani 1 1 d . . . . .
C1A C 0.8300(11) 0.025(3) 0.789(5) 0.031(3) Uani 0.632(4) 1 d D . P A 1
C2A C 0.896(2) -0.087(3) 0.806(5) 0.047(3) Uani 0.632(4) 1 d D . P A 1
H2AA H 0.8620 -0.1678 0.7869 0.057 Uiso 0.632(4) 1 calc R U P A 1
C3A C 1.0159(15) -0.0612(15) 0.8556(18) 0.0557(11) Uani 0.632(4) 1 d D . P A 1
H3A H 1.0764 -0.1237 0.8799 0.067 Uiso 0.632(4) 1 calc R U P A 1
S1A S 1.04529(19) 0.0928(3) 0.8688(3) 0.0616(7) Uani 0.632(4) 1 d D . P A 1
C4A C 0.898(2) 0.130(3) 0.821(6) 0.046(2) Uani 0.632(4) 1 d D . P A 1
H4A H 0.8675 0.2120 0.8172 0.055 Uiso 0.632(4) 1 calc R U P A 1
C1B C 0.828(2) 0.007(6) 0.795(8) 0.031(3) Uani 0.368(4) 1 d D . P A 2
C2B C 0.902(4) 0.113(5) 0.822(11) 0.046(2) Uani 0.368(4) 1 d D . P A 2
H2B H 0.8756 0.1966 0.8154 0.055 Uiso 0.368(4) 1 calc R U P A 2
C3B C 1.0190(17) 0.0759(19) 0.860(2) 0.0616(7) Uani 0.368(4) 1 d D . P A 2
H3B H 1.0849 0.1322 0.8882 0.074 Uiso 0.368(4) 1 calc R U P A 2
S1B S 1.0343(6) -0.0816(6) 0.8513(7) 0.0557(11) Uani 0.368(4) 1 d D . P A 2
C4B C 0.886(4) -0.104(5) 0.807(10) 0.047(3) Uani 0.368(4) 1 d D . P A 2
H4B H 0.8472 -0.1833 0.7916 0.057 Uiso 0.368(4) 1 calc R U P A 2
C5 C 0.6373(2) -0.0359(2) 0.8841(2) 0.0270(6) Uani 1 1 d . . . . .
C6 C 0.6536(2) 0.0496(2) 0.9719(2) 0.0279(6) Uani 1 1 d . . . . .
H6 H 0.6635 0.1359 0.9610 0.033 Uiso 1 1 calc R U . . .
C7 C 0.6550(3) 0.0064(2) 1.0763(2) 0.0275(6) Uani 1 1 d . . . . .
H7 H 0.6657 0.0630 1.1380 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6406(3) -0.1202(3) 1.0899(2) 0.0312(6) Uani 1 1 d . . . . .
O1 O 0.6419(2) -0.1686(2) 1.19004(19) 0.0449(6) Uani 1 1 d . . . . .
H1O H 0.643(3) -0.116(3) 1.236(3) 0.039(10) Uiso 1 1 d . . . . .
C9 C 0.6222(3) -0.2039(3) 0.9998(3) 0.0389(7) Uani 1 1 d . . . . .
H9 H 0.6105 -0.2900 1.0096 0.047 Uiso 1 1 calc R U . . .
C10 C 0.6209(3) -0.1613(3) 0.8960(3) 0.0368(7) Uani 1 1 d . . . . .
H10 H 0.6089 -0.2176 0.8337 0.044 Uiso 1 1 calc R U . . .
S2 S 0.68243(6) -0.58591(6) 0.91624(6) 0.02773(15) Uani 1 1 d . . . . .
F1 F 0.8565(2) -0.4355(2) 1.0402(2) 0.0732(7) Uani 1 1 d . . . . .
F2 F 0.9102(2) -0.6246(3) 1.0382(2) 0.0843(8) Uani 1 1 d . . . . .
F3 F 0.8668(2) -0.5079(2) 0.8870(2) 0.0749(7) Uani 1 1 d . . . . .
O2 O 0.6788(2) -0.68775(19) 0.84137(19) 0.0448(6) Uani 1 1 d . . . . .
O3 O 0.61674(18) -0.47621(18) 0.85418(18) 0.0352(5) Uani 1 1 d . . . . .
O4 O 0.6632(2) -0.6179(2) 1.01759(17) 0.0408(5) Uani 1 1 d . . . . .
C11 C 0.8375(3) -0.5354(4) 0.9744(3) 0.0491(9) 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 C1B 2.070(19) . ?
I1 C1A 2.088(11) . ?
I1 C5 2.102(3) . ?
C1A C4A 1.36(2) . ?
C1A C2A 1.41(2) . ?
C2A C3A 1.36(3) . ?
C2A H2AA 0.9500 . ?
C3A S1A 1.682(15) . ?
C3A H3A 0.9500 . ?
S1A C4A 1.69(2) . ?
C4A H4A 0.9500 . ?
C1B C4B 1.36(4) . ?
C1B C2B 1.40(3) . ?
C2B C3B 1.36(4) . ?
C2B H2B 0.9500 . ?
C3B S1B 1.706(18) . ?
C3B H3B 0.9500 . ?
S1B C4B 1.69(3) . ?
C4B H4B 0.9500 . ?
C5 C10 1.376(4) . ?
C5 C6 1.384(4) . ?
C6 C7 1.387(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(4) . ?
C7 H7 0.9500 . ?
C8 O1 1.358(3) . ?
C8 C9 1.387(4) . ?
O1 H1O 0.80(3) . ?
C9 C10 1.379(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
S2 O2 1.430(2) . ?
S2 O4 1.435(2) . ?
S2 O3 1.452(2) . ?
S2 C11 1.811(4) . ?
F1 C11 1.312(4) . ?
F2 C11 1.323(4) . ?
F3 C11 1.329(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
C1B I1 C5 93(3) . . ?
C1A I1 C5 97.3(14) . . ?
C4A C1A C2A 114.6(9) . . ?
C4A C1A I1 123(2) . . ?
C2A C1A I1 122.0(19) . . ?
C3A C2A C1A 110.0(17) . . ?
C3A C2A H2AA 125.0 . . ?
C1A C2A H2AA 125.0 . . ?
C2A C3A S1A 112.8(16) . . ?
C2A C3A H3A 123.6 . . ?
S1A C3A H3A 123.6 . . ?
C3A S1A C4A 92.4(12) . . ?
C1A C4A S1A 110.0(14) . . ?
C1A C4A H4A 125.0 . . ?
S1A C4A H4A 125.0 . . ?
C4B C1B C2B 115.2(15) . . ?
C4B C1B I1 124(4) . . ?
C2B C1B I1 121(3) . . ?
C3B C2B C1B 109(3) . . ?
C3B C2B H2B 125.3 . . ?
C1B C2B H2B 125.3 . . ?
C2B C3B S1B 113(2) . . ?
C2B C3B H3B 123.5 . . ?
S1B C3B H3B 123.5 . . ?
C4B S1B C3B 91.7(18) . . ?
C1B C4B S1B 110(2) . . ?
C1B C4B H4B 124.8 . . ?
S1B C4B H4B 124.8 . . ?
C10 C5 C6 122.5(2) . . ?
C10 C5 I1 117.98(19) . . ?
C6 C5 I1 119.5(2) . . ?
C5 C6 C7 118.4(2) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C8 C7 C6 119.5(2) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
O1 C8 C7 122.4(2) . . ?
O1 C8 C9 116.5(3) . . ?
C7 C8 C9 121.1(3) . . ?
C8 O1 H1O 113(2) . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C5 C10 C9 118.9(3) . . ?
C5 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
O2 S2 O4 115.71(13) . . ?
O2 S2 O3 114.05(13) . . ?
O4 S2 O3 114.09(13) . . ?
O2 S2 C11 103.14(16) . . ?
O4 S2 C11 104.73(15) . . ?
O3 S2 C11 103.04(15) . . ?
F1 C11 F2 108.2(3) . . ?
F1 C11 F3 107.7(3) . . ?
F2 C11 F3 108.2(3) . . ?
F1 C11 S2 111.9(3) . . ?
F2 C11 S2 110.7(3) . . ?
F3 C11 S2 109.9(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
C4A C1A C2A C3A 1(8) . . . . ?
I1 C1A C2A C3A -175(3) . . . . ?
C1A C2A C3A S1A -5(5) . . . . ?
C2A C3A S1A C4A 5(4) . . . . ?
C2A C1A C4A S1A 2(8) . . . . ?
I1 C1A C4A S1A 178(3) . . . . ?
C3A S1A C4A C1A -4(5) . . . . ?
C4B C1B C2B C3B -3(14) . . . . ?
I1 C1B C2B C3B -177(6) . . . . ?
C1B C2B C3B S1B 5(11) . . . . ?
C2B C3B S1B C4B -4(8) . . . . ?
C2B C1B C4B S1B 0(13) . . . . ?
I1 C1B C4B S1B 174(5) . . . . ?
C3B S1B C4B C1B 2(8) . . . . ?
C10 C5 C6 C7 0.9(4) . . . . ?
I1 C5 C6 C7 -176.9(2) . . . . ?
C5 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 O1 179.6(3) . . . . ?
C6 C7 C8 C9 -1.5(5) . . . . ?
O1 C8 C9 C10 -179.4(3) . . . . ?
C7 C8 C9 C10 1.6(5) . . . . ?
C6 C5 C10 C9 -0.8(5) . . . . ?
I1 C5 C10 C9 177.0(2) . . . . ?
C8 C9 C10 C5 -0.4(5) . . . . ?
O2 S2 C11 F1 175.7(3) . . . . ?
O4 S2 C11 F1 -62.8(3) . . . . ?
O3 S2 C11 F1 56.8(3) . . . . ?
O2 S2 C11 F2 -63.5(3) . . . . ?
O4 S2 C11 F2 58.0(3) . . . . ?
O3 S2 C11 F2 177.6(2) . . . . ?
O2 S2 C11 F3 56.0(3) . . . . ?
O4 S2 C11 F3 177.5(2) . . . . ?
O3 S2 C11 F3 -62.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O3 0.80(3) 1.93(3) 2.706(3) 163(3) 4_556

_refine_diff_density_max         0.586
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.103

####################################################################### 
# 
# 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_20171016-1
_database_code_depnum_ccdc_archive 'CCDC 1855607'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-20 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         'C10 H8 I O S, C F3 O3 S'
_chemical_formula_sum            'C11 H8 F3 I O4 S2'
_chemical_formula_weight         452.19

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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 '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'

_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                   12.4345(7)
_cell_length_b                   10.6515(7)
_cell_length_c                   12.6308(9)
_cell_angle_alpha                90
_cell_angle_beta                 115.594(8)
_cell_angle_gamma                90
_cell_volume                     1508.75(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2644
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.991
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    2.442
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.585
_exptl_absorpt_process_details   
;
FS_PROCESS, CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 RX
_diffrn_measurement_device       
;
Crystal Goniometer
;
_diffrn_measurement_device_type  
;
Rigaku RAXIS conversion
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            13623
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.237
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3454
_reflns_number_gt                2720
_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 r12 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_structure_solution    
;
Sir 2004, release 1.00, M. C. Burla, R. Caliandro, M. Camalli,
B. Carrozzini, G. L. Cascarano, L. De Caro, C. Giacovazzo,
G. Polidori & R. Spagna, J. Appl. Cryst. (2005). 38, 381-388.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury 3.3 (Build RC5)
POV-Ray for Windows- version 3.7.0.msvc10.win64
;
_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)+(0.0363P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3454
_refine_ls_number_parameters     208
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0686
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_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 0.85733(2) 0.02482(2) 0.76898(2) 0.03644(9) Uani 1 1 d D . . . .
O1 O 0.8622(3) -0.1695(2) 0.30970(19) 0.0544(7) Uani 1 1 d . . . . .
H7 H 0.8610 -0.1109 0.2648 0.082 Uiso 1 1 calc R U . . .
C1 C 0.8642(3) -0.0355(3) 0.6134(3) 0.0352(7) Uani 1 1 d . . . . .
C2 C 0.8476(3) 0.0504(3) 0.5251(3) 0.0359(7) Uani 1 1 d . . . . .
H2 H 0.8372 0.1372 0.5354 0.043 Uiso 1 1 calc R U . . .
C3 C 0.8465(3) 0.0065(3) 0.4223(3) 0.0369(8) Uani 1 1 d . . . . .
H3 H 0.8349 0.0631 0.3601 0.044 Uiso 1 1 calc R U . . .
C4 C 0.8626(3) -0.1206(3) 0.4096(3) 0.0407(8) Uani 1 1 d . . . . .
C5 C 0.8795(4) -0.2038(3) 0.4987(3) 0.0525(10) Uani 1 1 d . . . . .
H5 H 0.8904 -0.2906 0.4888 0.063 Uiso 1 1 calc R U . . .
C6 C 0.8805(3) -0.1618(3) 0.6020(3) 0.0462(9) Uani 1 1 d . . . . .
H6 H 0.8923 -0.2185 0.6641 0.055 Uiso 1 1 calc R U . . .
C7 C 0.6738(4) 0.0296(12) 0.7091(17) 0.035(2) Uani 0.584(4) 1 d D U P A 1
C8 C 0.6021(11) -0.0784(10) 0.6882(11) 0.0638(11) Uani 0.584(4) 1 d D . P A 1
H8 H 0.6379 -0.1571 0.7067 0.077 Uiso 0.584(4) 1 d R U P A 1
C9 C 0.4817(15) -0.0704(11) 0.642(2) 0.060(2) Uani 0.584(4) 1 d D U P A 1
H9 H 0.4246 -0.1361 0.6214 0.072 Uiso 0.584(4) 1 calc R U P A 1
C10 C 0.4639(15) 0.0530(11) 0.6313(19) 0.058(2) Uani 0.584(4) 1 d D U P A 1
H10 H 0.3872 0.0856 0.6029 0.070 Uiso 0.584(4) 1 d R U P A 1
S1 S 0.5899(2) 0.1582(2) 0.6666(2) 0.0573(7) Uani 0.584(4) 1 d D . P A 1
C7' C 0.6747(4) -0.0022(18) 0.701(3) 0.035(2) Uani 0.416(4) 1 d D U P A 2
C8' C 0.5969(12) 0.1004(12) 0.6712(12) 0.0573(7) Uani 0.416(4) 1 d D . P A 2
H8' H 0.6278 0.1811 0.6780 0.069 Uiso 0.416(4) 1 d R U P A 2
C9' C 0.475(2) 0.0873(17) 0.631(3) 0.058(2) Uani 0.416(4) 1 d D U P A 2
H9' H 0.4125 0.1472 0.6019 0.070 Uiso 0.416(4) 1 calc R U P A 2
C10' C 0.474(2) -0.0364(16) 0.646(3) 0.060(2) Uani 0.416(4) 1 d D U P A 2
H10' H 0.4015 -0.0762 0.6265 0.072 Uiso 0.416(4) 1 d R U P A 2
S1' S 0.6076(3) -0.1361(3) 0.6917(4) 0.0638(11) Uani 0.416(4) 1 d D . P A 2
S2 S 0.81872(8) 0.41648(8) 0.58135(6) 0.03668(19) Uani 1 1 d . . . . .
F1 F 0.6482(3) 0.5736(3) 0.4615(2) 0.0893(8) Uani 1 1 d . . . . .
F2 F 0.6366(3) 0.4947(3) 0.6115(3) 0.0831(8) Uani 1 1 d . . . . .
F3 F 0.5916(2) 0.3831(3) 0.4570(2) 0.0984(9) Uani 1 1 d . . . . .
O2 O 0.8216(2) 0.3121(2) 0.65379(19) 0.0552(7) Uani 1 1 d . . . . .
O3 O 0.8364(2) 0.3871(2) 0.47951(18) 0.0524(6) Uani 1 1 d . . . . .
O4 O 0.8859(2) 0.5246(2) 0.6465(2) 0.0457(6) Uani 1 1 d . . . . .
C11 C 0.6657(4) 0.4696(4) 0.5246(4) 0.0588(11) 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 C7' 2.071(4) . ?
I1 C7 2.071(4) . ?
I1 C1 2.103(3) . ?
O1 C4 1.363(3) . ?
O1 H7 0.8400 . ?
C1 C6 1.377(4) . ?
C1 C2 1.388(4) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(4) . ?
C5 C6 1.374(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.409(15) . ?
C7 S1 1.664(12) . ?
C8 C9 1.354(18) . ?
C8 H8 0.9300 . ?
C9 C10 1.329(11) . ?
C9 H9 0.9500 . ?
C10 S1 1.818(13) . ?
C10 H10 0.9300 . ?
C7' C8' 1.399(17) . ?
C7' S1' 1.632(17) . ?
C8' C9' 1.38(2) . ?
C8' H8' 0.9300 . ?
C9' C10' 1.332(14) . ?
C9' H9' 0.9500 . ?
C10' S1' 1.840(19) . ?
C10' H10' 0.9300 . ?
S2 O2 1.430(2) . ?
S2 O3 1.430(2) . ?
S2 O4 1.452(3) . ?
S2 C11 1.810(5) . ?
F1 C11 1.326(5) . ?
F2 C11 1.323(5) . ?
F3 C11 1.321(5) . ?

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
C7' I1 C1 92.7(8) . . ?
C7 I1 C1 98.6(5) . . ?
C4 O1 H7 109.5 . . ?
C6 C1 C2 122.5(3) . . ?
C6 C1 I1 117.6(2) . . ?
C2 C1 I1 119.9(2) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
O1 C4 C5 116.7(3) . . ?
O1 C4 C3 122.4(3) . . ?
C5 C4 C3 120.8(3) . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
C8 C7 S1 110.7(6) . . ?
C8 C7 I1 123.8(8) . . ?
S1 C7 I1 125.2(6) . . ?
C9 C8 C7 121.4(11) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.5 . . ?
C10 C9 C8 102.2(16) . . ?
C10 C9 H9 128.9 . . ?
C8 C9 H9 128.9 . . ?
C9 C10 S1 119.7(16) . . ?
C9 C10 H10 120.5 . . ?
S1 C10 H10 119.7 . . ?
C7 S1 C10 85.7(5) . . ?
C8' C7' S1' 112.9(7) . . ?
C8' C7' I1 120.7(11) . . ?
S1' C7' I1 125.9(10) . . ?
C9' C8' C7' 122.8(13) . . ?
C9' C8' H8' 118.0 . . ?
C7' C8' H8' 119.2 . . ?
C10' C9' C8' 97(2) . . ?
C10' C9' H9' 131.4 . . ?
C8' C9' H9' 131.4 . . ?
C9' C10' S1' 124(2) . . ?
C9' C10' H10' 118.9 . . ?
S1' C10' H10' 117.4 . . ?
C7' S1' C10' 83.3(8) . . ?
O2 S2 O3 115.72(15) . . ?
O2 S2 O4 113.85(15) . . ?
O3 S2 O4 114.18(15) . . ?
O2 S2 C11 103.16(18) . . ?
O3 S2 C11 104.82(17) . . ?
O4 S2 C11 103.06(18) . . ?
F3 C11 F2 108.2(4) . . ?
F3 C11 F1 107.9(4) . . ?
F2 C11 F1 107.2(4) . . ?
F3 C11 S2 111.0(3) . . ?
F2 C11 S2 110.6(3) . . ?
F1 C11 S2 111.8(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 0.6(5) . . . . ?
I1 C1 C2 C3 -176.7(3) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 O1 179.9(3) . . . . ?
C2 C3 C4 C5 0.1(6) . . . . ?
O1 C4 C5 C6 -179.7(3) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C4 C5 C6 C1 0.1(6) . . . . ?
C2 C1 C6 C5 -0.5(6) . . . . ?
I1 C1 C6 C5 176.9(3) . . . . ?
S1 C7 C8 C9 -1(2) . . . . ?
I1 C7 C8 C9 -175.5(15) . . . . ?
C7 C8 C9 C10 -2(3) . . . . ?
C8 C9 C10 S1 5(3) . . . . ?
C8 C7 S1 C10 2.9(14) . . . . ?
I1 C7 S1 C10 177.2(14) . . . . ?
C9 C10 S1 C7 -5(2) . . . . ?
S1' C7' C8' C9' -4(3) . . . . ?
I1 C7' C8' C9' -177(2) . . . . ?
C7' C8' C9' C10' 6(4) . . . . ?
C8' C9' C10' S1' -6(4) . . . . ?
C8' C7' S1' C10' 0(2) . . . . ?
I1 C7' S1' C10' 172(2) . . . . ?
C9' C10' S1' C7' 4(3) . . . . ?
O2 S2 C11 F3 -64.4(3) . . . . ?
O3 S2 C11 F3 57.1(3) . . . . ?
O4 S2 C11 F3 176.9(3) . . . . ?
O2 S2 C11 F2 55.7(3) . . . . ?
O3 S2 C11 F2 177.3(3) . . . . ?
O4 S2 C11 F2 -63.0(3) . . . . ?
O2 S2 C11 F1 175.1(3) . . . . ?
O3 S2 C11 F1 -63.4(3) . . . . ?
O4 S2 C11 F1 56.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H7 O4 0.84 1.89 2.691(3) 159.2 4_565

_refine_diff_density_max         1.241
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.113

