# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_3d
_database_code_depnum_ccdc_archive 'CCDC 1502422'
_audit_update_record             
;
2017-02-28 deposited with the CCDC.
2017-05-11 downloaded from the CCDC.
;

_vrf_PLAT411_3d                  
;
PROBLEM: Short Inter H...H Contact   H8     ..  H13     .       1.68 Ang.
RESPONSE: Crystals of this compound were of poor x-ray quality and this
          should be regarded as a qualitative structural determination. 
          Although given here is our best model with the data in hand, 
          it is reasonable to suppose that the phenyl ring (atoms C10 to 
          C15) would be slightly differently oriented in a more 
          accurate crystal structure of this sample (so that such a
          short H...H contact between symmetry-related molecules would
          not be noted).
;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H9 I O2'
_chemical_formula_sum            'C15 H9 I O2'
_chemical_formula_weight         348.12

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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   18.8983(13)
_cell_length_b                   5.7625(4)
_cell_length_c                   13.2709(12)
_cell_angle_alpha                90
_cell_angle_beta                 116.426(8)
_cell_angle_gamma                90
_cell_volume                     1294.21(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4997
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      23.28

_exptl_crystal_description       laminar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   0.6104
_exptl_transmission_factor_max   0.7449
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.464
_shelx_estimated_absorpt_T_min   0.665
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7989
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.714
_diffrn_reflns_theta_max         23.321
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.809
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.809
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.804
_reflns_number_total             1877
_reflns_number_gt                1686
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.798

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1183P)²+21.1769P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.46(17)
_chemical_absolute_configuration racemic
_refine_ls_number_reflns         1877
_refine_ls_number_parameters     140
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1954
_refine_ls_wR_factor_gt          0.1764
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.102
_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 -0.06770(6) 0.9844(14) 0.80987(9) 0.0534(5) Uani 1 1 d . . . . .
O1 O 0.0638(12) 0.130(4) 0.6495(18) 0.089(6) Uani 1 1 d D . . . .
C1 C -0.03167(7) 0.69198(2) 0.72872(11) 0.080(6) Uani 1 1 d G U . . .
C2 C 0.04203(8) 0.60525(16) 0.80222(13) 0.081(6) Uani 1 1 d G U . . .
O2 O 0.07265(10) 0.4128(2) 0.77196(16) 0.075(5) Uani 1 1 d G U . . .
C3 C 0.02955(13) 0.3072(2) 0.66820(17) 0.071(5) Uani 1 1 d DG U . . .
C4 C -0.04415(11) 0.39389(15) 0.59470(13) 0.070(5) Uani 1 1 d G U . . .
C5 C -0.07477(8) 0.58629(11) 0.62496(11) 0.070(5) Uani 1 1 d G U . . .
C6 C -0.14569(11) 0.6802(4) 0.55828(16) 0.065(4) Uani 1 1 d . U . . .
H6 H -0.1642 0.8093 0.5813 0.078 Uiso 1 1 calc R U . . .
C7 C -0.1913(16) 0.576(5) 0.452(2) 0.070(6) Uani 1 1 d . U . . .
H7 H -0.2395 0.6413 0.4030 0.084 Uiso 1 1 calc R U . . .
C8 C -0.1659(17) 0.386(5) 0.421(2) 0.071(6) Uani 1 1 d . U . . .
H8 H -0.1990 0.3139 0.3539 0.085 Uiso 1 1 calc R U . . .
C9 C -0.09084(11) 0.2901(4) 0.48645(16) 0.068(5) Uani 1 1 d . U . . .
H9 H -0.0722 0.1652 0.4609 0.082 Uiso 1 1 calc R U . . .
C10 C 0.10602(17) 0.6516(9) 0.9242(3) 0.070(5) Uani 1 1 d G U . . .
C11 C 0.1509(4) 0.8531(12) 0.9465(5) 0.067(5) Uani 1 1 d G U . . .
H11 H 0.1424 0.9577 0.8889 0.080 Uiso 1 1 calc R U . . .
C12 C 0.2086(4) 0.8982(17) 1.0551(6) 0.062(5) Uani 1 1 d G U . . .
H12 H 0.2386 1.0330 1.0701 0.074 Uiso 1 1 calc R U . . .
C13 C 0.2213(3) 0.742(2) 1.1412(4) 0.066(5) Uani 1 1 d G U . . .
H13 H 0.2598 0.7720 1.2138 0.080 Uiso 1 1 calc R U . . .
C14 C 0.1764(4) 0.5404(18) 1.1188(4) 0.071(5) Uani 1 1 d G U . . .
H14 H 0.1849 0.4358 1.1765 0.085 Uiso 1 1 calc R U . . .
C15 C 0.1187(3) 0.4952(12) 1.0103(5) 0.064(4) Uani 1 1 d G U . . .
H15 H 0.0887 0.3604 0.9953 0.077 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 C1 2.262(6) . ?
O1 C3 1.289(15) . ?
C1 C2 1.3900 . ?
C1 C5 1.3900 . ?
C2 O2 1.3900 . ?
C2 C10 1.553(4) . ?
O2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C4 C9 1.439(3) . ?
C5 C6 1.348(2) . ?
C6 C7 1.42(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.33(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.40(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.3900 . ?
C10 C15 1.3900 . ?
C11 C12 1.3900 . ?
C11 H11 0.9300 . ?
C12 C13 1.3900 . ?
C12 H12 0.9300 . ?
C13 C14 1.3900 . ?
C13 H13 0.9300 . ?
C14 C15 1.3900 . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 120.0 . . ?
C2 C1 I1 110.72(6) . . ?
C5 C1 I1 129.07(5) . . ?
C1 C2 O2 120.0 . . ?
C1 C2 C10 137.90(14) . . ?
O2 C2 C10 101.95(15) . . ?
C2 O2 C3 120.0 . . ?
O1 C3 C4 125.6(9) . . ?
O1 C3 O2 114.4(9) . . ?
C4 C3 O2 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 C9 118.07(14) . . ?
C3 C4 C9 121.93(14) . . ?
C6 C5 C4 123.41(13) . . ?
C6 C5 C1 116.59(13) . . ?
C4 C5 C1 120.0 . . ?
C5 C6 C7 118.0(13) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C8 C7 C6 121(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 123(3) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
C8 C9 C4 117.0(13) . . ?
C8 C9 H9 121.5 . . ?
C4 C9 H9 121.5 . . ?
C11 C10 C15 120.0 . . ?
C11 C10 C2 119.0(3) . . ?
C15 C10 C2 121.0(3) . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.0 . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?

_refine_diff_density_max         1.401
_refine_diff_density_min         -1.091
_refine_diff_density_rms         0.216

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1502423'
_audit_update_record             
;
2017-02-28 deposited with the CCDC.
2017-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H13 I O2'
_chemical_formula_sum            'C13 H13 I O2'
_chemical_formula_weight         328.13

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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   13.9685(19)
_cell_length_b                   7.1901(9)
_cell_length_c                   12.5256(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1258.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9811
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      31.49

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   0.5844
_exptl_transmission_factor_max   0.7464
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.529
_shelx_estimated_absorpt_T_min   0.632
_shelx_estimated_absorpt_T_max   0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22340
_diffrn_reflns_av_unetI/netI     0.0102
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.184
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             1204
_reflns_number_gt                1158
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0585P)²+0.5116P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.070(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1204
_refine_ls_number_parameters     95
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   1.339
_refine_ls_restrained_S_all      1.339
_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 0.18718(2) 0.2500 -0.21877(2) 0.0641(3) Uani 1 2 d S T P . .
O1 O 0.19099(18) 0.2500 0.1245(3) 0.0480(7) Uani 1 2 d S T P . .
O2 O 0.1239(3) 0.2500 0.2876(2) 0.0678(11) Uani 1 2 d S T P . .
C1 C 0.1138(3) 0.2500 0.1924(4) 0.0489(10) Uani 1 2 d S T P . .
C2 C 0.0276(3) 0.2500 0.1248(3) 0.0434(9) Uani 1 2 d S T P . .
C3 C -0.0686(3) 0.2500 0.1576(4) 0.0581(11) Uani 1 2 d S T P . .
H3A H -0.0851 0.2500 0.2295 0.070 Uiso 1 2 calc R U P . .
C4 C -0.1374(3) 0.2500 0.0788(5) 0.0657(14) Uani 1 2 d S T P . .
H4A H -0.2019 0.2500 0.0974 0.079 Uiso 1 2 calc R U P . .
C5 C -0.1114(3) 0.2500 -0.0281(5) 0.0634(13) Uani 1 2 d S T P . .
H5A H -0.1592 0.2500 -0.0797 0.076 Uiso 1 2 calc R U P . .
C6 C -0.0164(3) 0.2500 -0.0607(4) 0.0528(10) Uani 1 2 d S T P . .
H6A H -0.0006 0.2500 -0.1328 0.063 Uiso 1 2 calc R U P . .
C7 C 0.0552(3) 0.2500 0.0178(3) 0.0398(8) Uani 1 2 d S T P . .
C8 C 0.1612(3) 0.2500 0.0164(3) 0.0388(8) Uani 1 2 d S T P . .
C9 C 0.2311(3) 0.2500 -0.0578(3) 0.0388(8) Uani 1 2 d S T P . .
C10 C 0.3397(3) 0.2500 -0.0332(4) 0.0464(9) Uani 1 2 d S T P . .
C11 C 0.4035(4) 0.2500 -0.1339(4) 0.0643(13) Uani 1 2 d S T P . .
H11A H 0.4699 0.2500 -0.1110 0.097 Uiso 1 2 d S U P . .
H11B H 0.3911 0.3590 -0.1743 0.097 Uiso 1 1 d . U . . .
C12 C 0.3646(2) 0.0726(5) 0.0307(3) 0.0622(9) Uani 1 1 d . . . . .
H12A H 0.4319 0.0715 0.0464 0.093 Uiso 1 1 calc R U . . .
H12B H 0.3486 -0.0352 -0.0109 0.093 Uiso 1 1 calc R U . . .
H12C H 0.3289 0.0712 0.0961 0.093 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 C9 2.108(4) . ?
O1 C1 1.374(5) . ?
O1 C8 1.416(5) . ?
O2 C1 1.201(6) . ?
C1 C2 1.472(6) . ?
C2 C7 1.394(6) . ?
C2 C3 1.405(6) . ?
C3 C4 1.378(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.387(9) . ?
C4 H4A 0.9300 . ?
C5 C6 1.388(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.403(6) . ?
C6 H6A 0.9300 . ?
C7 C8 1.481(6) . ?
C8 C9 1.348(6) . ?
C9 C10 1.548(6) . ?
C10 C11 1.544(6) . ?
C10 C12 1.545(4) . ?
C10 C12 1.546(4) 7_565 ?
C11 H11A 0.9714 . ?
C11 H11B 0.9492 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C8 111.2(3) . . ?
O2 C1 O1 121.5(4) . . ?
O2 C1 C2 131.9(4) . . ?
O1 C1 C2 106.6(4) . . ?
C7 C2 C3 123.1(4) . . ?
C7 C2 C1 109.1(3) . . ?
C3 C2 C1 127.9(4) . . ?
C4 C3 C2 117.3(5) . . ?
C4 C3 H3A 121.4 . . ?
C2 C3 H3A 121.4 . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C6 122.3(5) . . ?
C4 C5 H5A 118.8 . . ?
C6 C5 H5A 118.8 . . ?
C5 C6 C7 118.4(5) . . ?
C5 C6 H6A 120.8 . . ?
C7 C6 H6A 120.8 . . ?
C2 C7 C6 118.5(4) . . ?
C2 C7 C8 106.7(3) . . ?
C6 C7 C8 134.8(4) . . ?
C9 C8 O1 116.5(3) . . ?
C9 C8 C7 137.1(4) . . ?
O1 C8 C7 106.4(3) . . ?
C8 C9 C10 124.9(4) . . ?
C8 C9 I1 116.7(3) . . ?
C10 C9 I1 118.4(3) . . ?
C11 C10 C12 107.0(3) . . ?
C11 C10 C12 107.0(3) . 7_565 ?
C12 C10 C12 111.3(4) . 7_565 ?
C11 C10 C9 113.7(4) . . ?
C12 C10 C9 108.9(2) . . ?
C12 C10 C9 108.9(2) 7_565 . ?
C10 C11 H11A 108.0 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 109.4 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.938
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.144

_shelxl_version_number           2013-4

