# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_mo_dfbgz0716_0m
_database_code_depnum_ccdc_archive 'CCDC 1500888'
_audit_update_record             
;
2016-08-24 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;

_audit_creation_date             2016-08-24T15:26:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
3-iodo-5-(methoxy(phenyl)methyl)-2-phenylselenophene
;
_chemical_name_common            'iodo methoxy phenyl methyl phenylselenophene'
_chemical_formula_moiety         'C18 H15 I O Se'
_chemical_formula_sum            'C18 H15 I O Se'
_chemical_formula_weight         453.16
_chemical_melting_point          357,4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  -C2yc


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_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                   20.300(5)
_cell_length_b                   5.882(5)
_cell_length_c                   27.651(5)
_cell_angle_alpha                90.000(2)
_cell_angle_beta                 94.075(3)
_cell_angle_gamma                90.0000(10)
_cell_volume                     3293(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8752
_cell_measurement_theta_min      2.409
_cell_measurement_theta_max      29.968

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.078
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.6266
_exptl_absorpt_correction_T_max  0.8622

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_number            17766
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         30.09
_diffrn_reflns_theta_full        30.09
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             4829
_reflns_number_gt                3406
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact G'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0169P)²+13.3815P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         4829
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.046
_refine_ls_wR_factor_ref         0.0699
_refine_ls_wR_factor_gt          0.0627
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.153

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I I 0.902393(12) 0.70530(5) 0.470802(8) 0.03200(9) Uani 1 1 d . . .
Se Se 0.952695(17) 0.54515(7) 0.310258(12) 0.01662(9) Uani 1 1 d . . .
O O 1.06753(13) 0.2538(5) 0.29720(9) 0.0295(7) Uani 1 1 d . . .
C2 C 0.85712(16) 0.8527(6) 0.34844(12) 0.0147(7) Uani 1 1 d . . .
C8 C 0.93667(16) 0.6075(6) 0.40402(11) 0.0164(8) Uani 1 1 d . . .
C15 C 1.20470(19) 0.0365(8) 0.44747(13) 0.0293(10) Uani 1 1 d . . .
H15 H 1.2399 0.0038 0.4698 0.035 Uiso 1 1 calc R . .
C7 C 0.80808(16) 0.8013(7) 0.31181(12) 0.0187(8) Uani 1 1 d . . .
H7 H 0.8096 0.664 0.2952 0.022 Uiso 1 1 calc R . .
C1 C 0.91041(15) 0.6882(6) 0.36058(11) 0.0147(7) Uani 1 1 d . . .
C4 C 0.8028(2) 1.2112(7) 0.36037(15) 0.0305(10) Uani 1 1 d . . .
H4 H 0.8009 1.3492 0.3766 0.037 Uiso 1 1 calc R . .
C6 C 0.75756(18) 0.9530(7) 0.30019(13) 0.0258(9) Uani 1 1 d . . .
H6 H 0.7253 0.9172 0.2758 0.031 Uiso 1 1 calc R . .
C12 C 1.10146(16) 0.1356(6) 0.38030(11) 0.0153(7) Uani 1 1 d . . .
C18 C 1.0978(2) 0.0711(8) 0.27284(13) 0.0332(11) Uani 1 1 d . . .
H18A H 1.1121 0.1243 0.2425 0.05 Uiso 1 1 calc R . .
H18B H 1.0664 -0.0498 0.267 0.05 Uiso 1 1 calc R . .
H18C H 1.1351 0.0159 0.2927 0.05 Uiso 1 1 calc R . .
C3 C 0.85388(18) 1.0613(7) 0.37231(13) 0.0226(8) Uani 1 1 d . . .
H3 H 0.8863 1.0997 0.3964 0.027 Uiso 1 1 calc R . .
C13 C 1.15228(17) 0.2869(7) 0.39002(13) 0.0223(8) Uani 1 1 d . . .
H13 H 1.1517 0.4255 0.3738 0.027 Uiso 1 1 calc R . .
C5 C 0.75440(19) 1.1566(7) 0.32431(15) 0.0306(10) Uani 1 1 d . . .
H5 H 0.72 1.2573 0.3165 0.037 Uiso 1 1 calc R . .
C10 C 1.00213(16) 0.3779(6) 0.35766(12) 0.0172(8) Uani 1 1 d . . .
C16 C 1.1547(2) -0.1185(7) 0.43969(14) 0.0336(10) Uani 1 1 d . . .
H16 H 1.1554 -0.2539 0.4571 0.04 Uiso 1 1 calc R . .
C11 C 1.04579(18) 0.1890(7) 0.34236(13) 0.0248(9) Uani 1 1 d . . .
H11 H 1.0186 0.0521 0.3375 0.03 Uiso 1 1 calc R . .
C17 C 1.1018(2) -0.0707(7) 0.40483(14) 0.0286(9) Uani 1 1 d . . .
H17 H 1.068 -0.1755 0.3985 0.034 Uiso 1 1 calc R . .
C14 C 1.20368(19) 0.2378(8) 0.42298(14) 0.0303(10) Uani 1 1 d . . .
H14 H 1.2379 0.3416 0.4287 0.036 Uiso 1 1 calc R . .
C9 C 0.98624(16) 0.4369(7) 0.40265(12) 0.0197(8) Uani 1 1 d . . .
H9 H 1.0062 0.371 0.4306 0.024 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
I C8 2.099(3) . ?
Se C10 1.872(3) . ?
Se C1 1.884(3) . ?
O C11 1.406(4) . ?
O C18 1.430(4) . ?
C2 C3 1.397(5) . ?
C2 C7 1.402(5) . ?
C2 C1 1.472(5) . ?
C8 C1 1.364(5) . ?
C8 C9 1.424(5) . ?
C15 C14 1.364(6) . ?
C15 C16 1.370(6) . ?
C7 C6 1.380(5) . ?
C4 C3 1.383(5) . ?
C4 C5 1.387(6) . ?
C6 C5 1.374(6) . ?
C12 C13 1.374(5) . ?
C12 C17 1.390(5) . ?
C12 C11 1.519(5) . ?
C13 C14 1.367(5) . ?
C10 C9 1.352(5) . ?
C10 C11 1.501(5) . ?
C16 C17 1.418(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 Se C1 88.12(15) . . ?
C11 O C18 112.8(3) . . ?
C3 C2 C7 118.4(3) . . ?
C3 C2 C1 121.9(3) . . ?
C7 C2 C1 119.7(3) . . ?
C1 C8 C9 117.0(3) . . ?
C1 C8 I 123.1(3) . . ?
C9 C8 I 119.7(2) . . ?
C14 C15 C16 121.0(4) . . ?
C6 C7 C2 120.4(4) . . ?
C8 C1 C2 131.6(3) . . ?
C8 C1 Se 109.0(2) . . ?
C2 C1 Se 119.4(2) . . ?
C3 C4 C5 120.3(4) . . ?
C5 C6 C7 120.7(4) . . ?
C13 C12 C17 119.4(3) . . ?
C13 C12 C11 120.8(3) . . ?
C17 C12 C11 119.7(3) . . ?
C4 C3 C2 120.4(4) . . ?
C14 C13 C12 121.4(4) . . ?
C6 C5 C4 119.7(4) . . ?
C9 C10 C11 129.3(3) . . ?
C9 C10 Se 111.0(3) . . ?
C11 C10 Se 119.3(2) . . ?
C15 C16 C17 119.4(4) . . ?
O C11 C10 106.2(3) . . ?
O C11 C12 113.8(3) . . ?
C10 C11 C12 112.6(3) . . ?
C12 C17 C16 118.9(4) . . ?
C15 C14 C13 119.9(4) . . ?
C10 C9 C8 114.9(3) . . ?

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH/CH2Cl2'
####################################################################### 
# 
# 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_p2c
_database_code_depnum_ccdc_archive 'CCDC 1500889'
_audit_update_record             
;
2016-08-24 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;

_audit_creation_date             2016-04-11T09:47:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
        3-iodo-5-isopropoxy-2,4-diphenylselenophene
;
_chemical_name_common            3-iodo-5-isopropoxy-2,4-diphenylselenophene
_chemical_formula_moiety         'C20 H19 I O Se'
_chemical_formula_sum            'C20 H19 I O Se'
_chemical_formula_weight         481.21
_chemical_melting_point          361,6

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2/c
_symmetry_space_group_name_Hall  -P2yc
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   19.0809(7)
_cell_length_b                   5.7136(2)
_cell_length_c                   17.2112(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.1750(10)
_cell_angle_gamma                90
_cell_volume                     1846.87(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9883
_cell_measurement_theta_min      2.404
_cell_measurement_theta_max      29.61

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.3743
_exptl_absorpt_correction_T_max  0.5885

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_number            15842
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.4
_diffrn_reflns_theta_max         29.63
_diffrn_reflns_theta_full        29.63
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             5190
_reflns_number_gt                4727
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact G'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.8714P] 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       none
_refine_ls_number_reflns         5190
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.0495
_refine_ls_wR_factor_gt          0.0482
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_restrained_S_all      1.07
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.718
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.089

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I I 0.938372(6) 0.64647(2) 0.618184(6) 0.01604(4) Uani 1 1 d . . .
Se Se 0.735061(9) 0.48643(3) 0.730479(9) 0.01336(4) Uani 1 1 d . . .
O O 0.61614(7) 0.2541(2) 0.62125(7) 0.0165(2) Uani 1 1 d . . .
C8 C 0.84347(9) 0.5476(3) 0.65388(9) 0.0120(3) Uani 1 1 d . . .
C2 C 0.85748(9) 0.7863(3) 0.78286(9) 0.0122(3) Uani 1 1 d . . .
C1 C 0.82294(9) 0.6241(3) 0.72138(9) 0.0120(3) Uani 1 1 d . . .
C9 C 0.79725(9) 0.3833(3) 0.60694(9) 0.0127(3) Uani 1 1 d . . .
H9 H 0.8072 0.3198 0.559 0.015 Uiso 1 1 calc R . .
C17 C 0.65040(9) 0.2634(3) 0.46137(10) 0.0157(3) Uani 1 1 d . . .
H17 H 0.6281 0.4014 0.4759 0.019 Uiso 1 1 calc R . .
C10 C 0.73803(9) 0.3260(3) 0.63669(9) 0.0128(3) Uani 1 1 d . . .
C12 C 0.67952(9) 0.1045(3) 0.51895(9) 0.0120(3) Uani 1 1 d . . .
C18 C 0.55429(9) 0.1036(3) 0.60462(10) 0.0169(3) Uani 1 1 d . . .
H18 H 0.5515 0.0338 0.5509 0.02 Uiso 1 1 calc R . .
C3 C 0.88482(10) 1.0005(3) 0.76201(10) 0.0165(3) Uani 1 1 d . . .
H3 H 0.8799 1.0431 0.708 0.02 Uiso 1 1 calc R . .
C16 C 0.65366(10) 0.2224(3) 0.38294(10) 0.0195(4) Uani 1 1 d . . .
H16 H 0.6325 0.3304 0.3438 0.023 Uiso 1 1 calc R . .
C7 C 0.86393(9) 0.7293(3) 0.86294(10) 0.0154(3) Uani 1 1 d . . .
H7 H 0.8451 0.5857 0.878 0.018 Uiso 1 1 calc R . .
C13 C 0.71255(10) -0.0967(3) 0.49748(11) 0.0189(4) Uani 1 1 d . . .
H13 H 0.7321 -0.2076 0.5365 0.023 Uiso 1 1 calc R . .
C6 C 0.89786(10) 0.8826(3) 0.92060(10) 0.0188(4) Uani 1 1 d . . .
H6 H 0.9018 0.8438 0.9749 0.023 Uiso 1 1 calc R . .
C4 C 0.91891(11) 1.1506(3) 0.81981(11) 0.0192(4) Uani 1 1 d . . .
H4 H 0.9377 1.2947 0.8052 0.023 Uiso 1 1 calc R . .
C14 C 0.71687(11) -0.1348(3) 0.41800(12) 0.0221(4) Uani 1 1 d . . .
H14 H 0.74 -0.2707 0.4031 0.027 Uiso 1 1 calc R . .
C15 C 0.68745(10) 0.0258(3) 0.36114(11) 0.0211(4) Uani 1 1 d . . .
H15 H 0.6905 0.0005 0.3073 0.025 Uiso 1 1 calc R . .
C5 C 0.92580(10) 1.0915(3) 0.89888(10) 0.0191(4) Uani 1 1 d . . .
H5 H 0.9497 1.1944 0.9382 0.023 Uiso 1 1 calc R . .
C11 C 0.68043(9) 0.1525(3) 0.60578(10) 0.0141(3) Uani 1 1 d . . .
H11 H 0.6896 0.0029 0.636 0.017 Uiso 1 1 calc R . .
C20 C 0.49161(11) 0.2626(4) 0.60467(14) 0.0288(4) Uani 1 1 d . . .
H20A H 0.4918 0.3859 0.5651 0.043 Uiso 1 1 calc R . .
H20B H 0.4947 0.3337 0.657 0.043 Uiso 1 1 calc R . .
H20C H 0.4475 0.1719 0.592 0.043 Uiso 1 1 calc R . .
C19 C 0.55637(12) -0.0917(4) 0.66480(16) 0.0351(5) Uani 1 1 d . . .
H19A H 0.5978 -0.1918 0.6631 0.053 Uiso 1 1 calc R . .
H19B H 0.5128 -0.1852 0.6524 0.053 Uiso 1 1 calc R . .
H19C H 0.5599 -0.0241 0.7177 0.053 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
I C8 2.0900(17) . ?
Se C10 1.8658(16) . ?
Se C1 1.8835(17) . ?
O C11 1.424(2) . ?
O C18 1.447(2) . ?
C8 C1 1.362(2) . ?
C8 C9 1.435(2) . ?
C2 C7 1.400(2) . ?
C2 C3 1.402(2) . ?
C2 C1 1.472(2) . ?
C9 C10 1.360(2) . ?
C17 C16 1.382(2) . ?
C17 C12 1.386(2) . ?
C10 C11 1.506(2) . ?
C12 C13 1.392(2) . ?
C12 C11 1.516(2) . ?
C18 C20 1.502(3) . ?
C18 C19 1.518(3) . ?
C3 C4 1.385(2) . ?
C16 C15 1.380(3) . ?
C7 C6 1.394(2) . ?
C13 C14 1.402(3) . ?
C6 C5 1.385(3) . ?
C4 C5 1.386(3) . ?
C14 C15 1.386(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 Se C1 88.26(7) . . ?
C11 O C18 114.83(13) . . ?
C1 C8 C9 116.69(16) . . ?
C1 C8 I 123.97(12) . . ?
C9 C8 I 119.30(12) . . ?
C7 C2 C3 118.87(15) . . ?
C7 C2 C1 120.77(15) . . ?
C3 C2 C1 120.35(15) . . ?
C8 C1 C2 130.95(16) . . ?
C8 C1 Se 109.36(12) . . ?
C2 C1 Se 119.69(12) . . ?
C10 C9 C8 114.47(15) . . ?
C16 C17 C12 120.37(17) . . ?
C9 C10 C11 128.93(15) . . ?
C9 C10 Se 111.19(12) . . ?
C11 C10 Se 119.83(12) . . ?
C17 C12 C13 119.63(16) . . ?
C17 C12 C11 121.31(15) . . ?
C13 C12 C11 118.94(15) . . ?
O C18 C20 105.19(15) . . ?
O C18 C19 112.31(16) . . ?
C20 C18 C19 111.65(18) . . ?
C4 C3 C2 120.35(16) . . ?
C15 C16 C17 120.50(17) . . ?
C6 C7 C2 120.23(17) . . ?
C12 C13 C14 119.66(16) . . ?
C5 C6 C7 120.12(16) . . ?
C3 C4 C5 120.38(17) . . ?
C15 C14 C13 119.98(17) . . ?
C16 C15 C14 119.84(17) . . ?
C6 C5 C4 120.03(16) . . ?
O C11 C10 105.33(13) . . ?
O C11 C12 113.43(14) . . ?
C10 C11 C12 110.35(14) . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH/CH2Cl2'
