# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_1
_database_code_depnum_ccdc_archive 'CCDC 1524674'
_audit_update_record             
;
2016-12-27 deposited with the CCDC.
2017-03-29 downloaded from the CCDC.
;
_audit_creation_date             2016-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_systematic        
'2,6-dibromo-9-selenabicyclo[3.3.1]nonane dibromine'
_chemical_formula_moiety         'C8 H12 Br4 Se'
_chemical_formula_sum            'C8 H12 Br4 Se'
_chemical_formula_weight         506.76
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.08110 2.30834 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.5472(14)
_cell_length_b                   7.8647(15)
_cell_length_c                   11.259(2)
_cell_angle_alpha                77.095(3)
_cell_angle_beta                 84.024(3)
_cell_angle_gamma                79.049(3)
_cell_volume                     638.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2845
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.863
_cell_measurement_theta_min      2.697
_exptl_absorpt_coefficient_mu    15.420
_exptl_absorpt_correction_T_max  0.8015
_exptl_absorpt_correction_T_min  0.1974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1393 before and 0.0529 after correction.
The Ratio of minimum to maximum transmission is 0.2463.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.6369
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             466.2116
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9185
_diffrn_reflns_theta_full        24.9996
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.70
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9796
_diffrn_measured_fraction_theta_max 0.9796
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              9
_reflns_limit_k_min              -8
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1707
_reflns_number_total             2206
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         2.5313
_refine_diff_density_min         -2.0681
_refine_diff_density_rms         0.4392
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             7.5518
_refine_ls_goodness_of_fit_ref   1.2306
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     117
_refine_ls_number_reflns         2206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0843
_refine_ls_restrained_S_all      1.2306
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2644
_refine_ls_wR_factor_ref         0.2999
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b), C6(H6a,H6b), C7(H7a,H7b)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Br1 Br 0.09678(13) 0.72868(13) 0.45554(11) 0.0402(6) Uani 1.000000 .
Br2 Br 0.14643(13) 0.78288(14) 0.21661(11) 0.0413(6) Uani 1.000000 .
Br3 Br 0.52326(16) 0.98159(14) 0.68399(13) 0.0633(7) Uani 1.000000 .
Br4 Br 0.32436(15) 0.22655(14) 0.96665(12) 0.0556(6) Uani 1.000000 .
Se1 Se 0.04508(13) 0.68373(15) 0.68344(11) 0.0456(6) Uani 1.000000 .
C1 C 0.20211(19) 0.83477(19) 0.72655(19) 0.037(3) Uani 1.000000 .
H1 H 0.14336(19) 0.95826(19) 0.70112(19) 0.045(4) Uiso 1.000000 R
C2 C 0.19845(19) 0.79372(19) 0.86288(19) 0.052(4) Uani 1.000000 .
H2a H 0.26762(19) 0.87099(19) 0.88715(19) 0.062(5) Uiso 1.000000 R
H2b H 0.07429(19) 0.82435(19) 0.89377(19) 0.062(5) Uiso 1.000000 R
C3 C 0.27125(19) 0.60083(19) 0.92754(19) 0.033(3) Uani 1.000000 .
H3a H 0.40231(19) 0.58094(19) 0.91804(19) 0.039(3) Uiso 1.000000 R
H3b H 0.23693(19) 0.58729(19) 1.01415(19) 0.039(3) Uiso 1.000000 R
C4 C 0.20357(19) 0.45967(19) 0.88009(19) 0.036(3) Uani 1.000000 .
H4 H 0.07457(19) 0.46821(19) 0.90559(19) 0.043(3) Uiso 1.000000 R
C5 C 0.21947(19) 0.46779(19) 0.74679(19) 0.037(3) Uani 1.000000 .
H5 H 0.17386(19) 0.36579(19) 0.73267(19) 0.045(4) Uiso 1.000000 R
C6 C 0.40585(19) 0.47213(19) 0.67716(19) 0.030(3) Uani 1.000000 .
H6a H 0.48544(19) 0.36261(19) 0.70886(19) 0.036(3) Uiso 1.000000 R
H6b H 0.39195(19) 0.47465(19) 0.59207(19) 0.036(3) Uiso 1.000000 R
C7 C 0.50039(19) 0.62912(19) 0.68299(19) 0.042(3) Uani 1.000000 .
H7a H 0.54122(19) 0.61126(19) 0.76445(19) 0.050(4) Uiso 1.000000 R
H7b H 0.60657(19) 0.62730(19) 0.62646(19) 0.050(4) Uiso 1.000000 R
C8 C 0.38146(19) 0.81221(19) 0.65274(19) 0.038(3) Uani 1.000000 .
H8 H 0.35874(19) 0.84014(19) 0.56579(19) 0.046(4) Uiso 1.000000 R


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
Br1 Br2 2.6263(17) . ?
Br1 Se1 2.5099(17) . ?
Br3 C8 1.968(2) . ?
Br4 C4 1.9733(18) . ?
Se1 C1 1.991(2) . ?
Se1 C5 1.9825(17) . ?
C1 H1 0.9800 . ?
C1 C2 1.495(3) . ?
C1 C8 1.515(2) . ?
C2 H2a 0.9700 . ?
C2 H2b 0.9700 . ?
C2 C3 1.551(2) . ?
C3 H3a 0.9700 . ?
C3 H3b 0.9700 . ?
C3 C4 1.522(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.481(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.540(2) . ?
C6 H6a 0.9700 . ?
C6 H6b 0.9700 . ?
C6 C7 1.555(2) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C7 C8 1.5325(19) . ?
C8 H8 0.9800 . ?

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
Se1 Br1 Br2 178.71(5) . . ?
C1 Se1 Br1 103.12(8) . . ?
C5 Se1 Br1 104.52(8) . . ?
C5 Se1 C1 90.54(8) . . ?
H1 C1 Se1 107.28(5) . . ?
C2 C1 Se1 105.79(11) . . ?
C2 C1 H1 107.28(8) . . ?
C8 C1 Se1 108.99(14) . . ?
C8 C1 H1 107.28(8) . . ?
C8 C1 C2 119.65(14) . . ?
H2a C2 C1 107.87(9) . . ?
H2b C2 C1 107.87(8) . . ?
H2b C2 H2a 107.2 . . ?
C3 C2 C1 117.75(16) . . ?
C3 C2 H2a 107.87(10) . . ?
C3 C2 H2b 107.87(8) . . ?
H3a C3 C2 108.65(8) . . ?
H3b C3 C2 108.65(11) . . ?
H3b C3 H3a 107.6 . . ?
C4 C3 C2 114.45(15) . . ?
C4 C3 H3a 108.65(8) . . ?
C4 C3 H3b 108.65(10) . . ?
C3 C4 Br4 107.63(12) . . ?
H4 C4 Br4 106.67(6) . . ?
H4 C4 C3 106.67(8) . . ?
C5 C4 Br4 110.07(12) . . ?
C5 C4 C3 118.51(14) . . ?
C5 C4 H4 106.67(8) . . ?
C4 C5 Se1 103.01(11) . . ?
H5 C5 Se1 107.73(6) . . ?
H5 C5 C4 107.73(9) . . ?
C6 C5 Se1 110.89(11) . . ?
C6 C5 C4 119.21(15) . . ?
C6 C5 H5 107.73(10) . . ?
H6a C6 C5 108.19(8) . . ?
H6b C6 C5 108.19(11) . . ?
H6b C6 H6a 107.3 . . ?
C7 C6 C5 116.40(15) . . ?
C7 C6 H6a 108.19(7) . . ?
C7 C6 H6b 108.19(11) . . ?
H7a C7 C6 108.59(10) . . ?
H7b C7 C6 108.59(9) . . ?
H7b C7 H7a 107.6 . . ?
C8 C7 C6 114.68(13) . . ?
C8 C7 H7a 108.59(12) . . ?
C8 C7 H7b 108.59(9) . . ?
C1 C8 Br3 108.01(14) . . ?
C7 C8 Br3 106.26(12) . . ?
C7 C8 C1 115.82(13) . . ?
H8 C8 Br3 108.85(7) . . ?
H8 C8 C1 108.85(11) . . ?
H8 C8 C7 108.85(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1524679'
_audit_update_record             
;
2016-12-27 deposited with the CCDC.
2017-03-29 downloaded from the CCDC.
;
_audit_creation_date             2016-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_systematic        
(2,6-Dibromo-9-selenabicyclo[3.3.1]nonan-9-yl)-dibromo-selenium
_chemical_formula_moiety         'C16 H24 Br6 Se3'
_chemical_formula_sum            'C16 H24 Br6 Se3'
_chemical_formula_weight         932.67
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.08110 2.30834 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.660(3)
_cell_length_b                   11.291(4)
_cell_length_c                   13.427(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.695(7)
_cell_angle_gamma                90
_cell_volume                     1160.8(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    452
_cell_measurement_temperature    150
_cell_measurement_theta_max      19.98
_cell_measurement_theta_min      2.36
_exptl_absorpt_coefficient_mu    15.080
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0866 before and 0.0534 after correction.
The Ratio of minimum to maximum transmission is 0.5422.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.6682
_exptl_crystal_density_meas      .
_exptl_crystal_description       needle
_exptl_crystal_F_000             861.2011
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.1728
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4482
_diffrn_reflns_theta_full        24.9944
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.36
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.9761
_diffrn_measured_fraction_theta_max 0.9761
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -9
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              -7
_reflns_number_gt                1209
_reflns_number_total             1998
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         2.0803
_refine_diff_density_min         -2.0267
_refine_diff_density_rms         0.5248
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             8.6403
_refine_ls_goodness_of_fit_ref   0.9052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      0.9052
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1115
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C8(H8), C1(H1), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C6(H6a,H6b), C3(H3a,H3b), C2(H2a,H2b)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Br1 Br 0.70282(19) 1.17578(13) 0.42475(11) 0.0295(4) Uani 1.000000 1 . . .
Br3 Br 0.13411(17) 1.53194(12) 0.32869(10) 0.0245(4) Uani 1.000000 1 . . .
Br2 Br 0.04167(18) 1.08303(12) 0.69598(11) 0.0297(4) Uani 1.000000 1 . . .
Se2 Se 0.0 1.5 0.5 0.0187(5) Uani 1.000000 2 S T P
Se1 Se 0.30352(17) 1.42014(11) 0.56880(10) 0.0189(3) Uani 1.000000 1 . . .
C7 C 0.1799(15) 1.1437(10) 0.5082(10) 0.018(3) Uani 1.000000 1 . . .
H7a H 0.0786(15) 1.1027(10) 0.4763(10) 0.022(4) Uiso 1.000000 1 R . .
H7b H 0.2668(15) 1.0825(10) 0.5279(10) 0.022(4) Uiso 1.000000 1 R . .
C6 C 0.2611(15) 1.2255(10) 0.4312(11) 0.022(3) Uani 1.000000 1 . . .
H6a H 0.3102(15) 1.1752(10) 0.3786(11) 0.027(4) Uiso 1.000000 1 R . .
H6b H 0.1658(15) 1.2728(10) 0.3997(11) 0.027(4) Uiso 1.000000 1 R . .
C4 C 0.5604(16) 1.2661(12) 0.5204(10) 0.021(3) Uani 1.000000 1 . . .
H4 H 0.6311(16) 1.3364(12) 0.5423(10) 0.025(4) Uiso 1.000000 1 R . .
C8 C 0.1202(18) 1.2052(11) 0.6007(9) 0.026(4) Uani 1.000000 1 . . .
H8 H 0.0154(18) 1.2536(11) 0.5810(9) 0.032(4) Uiso 1.000000 1 R . .
C1 C 0.2446(15) 1.2857(10) 0.6560(10) 0.017(3) Uani 1.000000 1 . . .
H1 H 0.1839(15) 1.3179(10) 0.7151(10) 0.021(4) Uiso 1.000000 1 R . .
C5 C 0.4042(16) 1.3113(11) 0.4674(10) 0.024(3) Uani 1.000000 1 . . .
H5 H 0.4418(16) 1.3596(11) 0.4094(10) 0.029(4) Uiso 1.000000 1 R . .
C3 C 0.5445(16) 1.1860(11) 0.6106(9) 0.022(3) Uani 1.000000 1 . . .
H3a H 0.4977(16) 1.1085(11) 0.5881(9) 0.027(4) Uiso 1.000000 1 R . .
H3b H 0.6627(16) 1.1722(11) 0.6402(9) 0.027(4) Uiso 1.000000 1 R . .
C2 C 0.4256(15) 1.2353(12) 0.6930(10) 0.023(3) Uani 1.000000 1 . . .
H2a H 0.4899(15) 1.2990(12) 0.7291(10) 0.028(4) Uiso 1.000000 1 R . .
H2b H 0.4046(15) 1.1711(12) 0.7414(10) 0.028(4) Uiso 1.000000 1 R . .


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
Br1 C4 1.991(13) . ?
Br3 Se2 2.5721(15) . ?
Br2 C8 1.986(13) . ?
Se2 Se1 2.6353(15) . ?
Se2 Se1 2.6353(15) 3_586 ?
Se1 C1 1.978(12) . ?
Se1 C5 2.006(13) . ?
C7 H7a 0.9900 . ?
C7 H7b 0.9900 . ?
C7 C6 1.531(16) . ?
C7 C8 1.507(17) . ?
C6 H6a 0.9900 . ?
C6 H6b 0.9900 . ?
C6 C5 1.531(17) . ?
C4 H4 1.0000 . ?
C4 C5 1.465(16) . ?
C4 C3 1.520(17) . ?
C8 H8 1.0000 . ?
C8 C1 1.498(16) . ?
C1 H1 1.0000 . ?
C1 C2 1.565(16) . ?
C5 H5 1.0000 . ?
C3 H3a 0.9900 . ?
C3 H3b 0.9900 . ?
C3 C2 1.556(16) . ?
C2 H2a 0.9900 . ?
C2 H2b 0.9900 . ?

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
Br3 Se2 Br3 180.0 3_586 . ?
Se1 Se2 Br3 90.58(4) 3_586 . ?
Se1 Se2 Br3 89.42(4) 3_586 3_586 ?
Se1 Se2 Br3 89.42(4) . . ?
Se1 Se2 Br3 90.58(4) . 3_586 ?
Se1 Se2 Se1 180.0 3_586 . ?
C1 Se1 Se2 104.8(3) . 3_586 ?
C5 Se1 Se2 109.0(4) . 3_586 ?
C5 Se1 C1 91.7(5) . . ?
H7b C7 H7a 107.6 . . ?
C6 C7 H7a 108.6(7) . . ?
C6 C7 H7b 108.6(6) . . ?
C8 C7 H7a 108.6(7) . . ?
C8 C7 H7b 108.6(7) . . ?
C8 C7 C6 114.7(10) . . ?
H6a C6 C7 107.8(7) . . ?
H6b C6 C7 107.8(7) . . ?
H6b C6 H6a 107.1 . . ?
C5 C6 C7 118.0(12) . . ?
C5 C6 H6a 107.8(7) . . ?
C5 C6 H6b 107.8(7) . . ?
H4 C4 Br1 107.1(4) . . ?
C5 C4 Br1 108.7(9) . . ?
C5 C4 H4 107.1(7) . . ?
C3 C4 Br1 105.5(8) . . ?
C3 C4 H4 107.1(7) . . ?
C3 C4 C5 120.7(11) . . ?
C7 C8 Br2 108.4(8) . . ?
H8 C8 Br2 107.1(4) . . ?
H8 C8 C7 107.1(7) . . ?
C1 C8 Br2 107.6(8) . . ?
C1 C8 C7 119.0(11) . . ?
C1 C8 H8 107.1(7) . . ?
C8 C1 Se1 109.0(9) . . ?
H1 C1 Se1 108.0(4) . . ?
H1 C1 C8 108.0(7) . . ?
C2 C1 Se1 104.6(8) . . ?
C2 C1 C8 118.8(11) . . ?
C2 C1 H1 108.0(7) . . ?
C6 C5 Se1 108.5(8) . . ?
C4 C5 Se1 102.0(9) . . ?
C4 C5 C6 120.0(11) . . ?
H5 C5 Se1 108.6(4) . . ?
H5 C5 C6 108.6(7) . . ?
H5 C5 C4 108.6(7) . . ?
H3a C3 C4 108.6(7) . . ?
H3b C3 C4 108.6(7) . . ?
H3b C3 H3a 107.57884604(2) . . ?
C2 C3 C4 114.5(10) . . ?
C2 C3 H3a 108.6(7) . . ?
C2 C3 H3b 108.6(7) . . ?
C3 C2 C1 115.9(11) . . ?
H2a C2 C1 108.3(7) . . ?
H2a C2 C3 108.3(7) . . ?
H2b C2 C1 108.3(6) . . ?
H2b C2 C3 108.3(7) . . ?
H2b C2 H2a 107.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1524676'
_audit_update_record             
;
2016-12-27 deposited with the CCDC.
2017-03-29 downloaded from the CCDC.
;
_audit_creation_date             2016-12-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_systematic        2,6-diiodo-9-selenabicyclo[3.3.1]nonane
_chemical_formula_moiety         'C8 H12 I2 Se'
_chemical_formula_sum            'C8 H12 I2 Se'
_chemical_formula_weight         440.95
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.08110 2.30834 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   13.3579(7)
_cell_length_b                   10.2925(5)
_cell_length_c                   7.8592(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.667(1)
_cell_angle_gamma                90
_cell_volume                     1073.22(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4436
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      30.634
_cell_measurement_theta_min      2.505
_exptl_absorpt_coefficient_mu    9.194
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.3830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1415 before and 0.0387 after correction.
The Ratio of minimum to maximum transmission is 0.5133.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.7289
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             796.7824
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6364
_diffrn_reflns_theta_full        28.9980
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.50
_diffrn_ambient_temperature      143.15
_diffrn_measured_fraction_theta_full 0.9832
_diffrn_measured_fraction_theta_max 0.9833
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -18
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                1355
_reflns_number_total             1409
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.7363
_refine_diff_density_min         -1.0938
_refine_diff_density_rms         0.1287
_refine_ls_d_res_high            0.7330
_refine_ls_d_res_low             8.1323
_refine_ls_goodness_of_fit_ref   1.0418
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    10
_refine_ls_number_parameters     50
_refine_ls_number_reflns         1409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0197
_refine_ls_R_factor_gt           0.0186
_refine_ls_restrained_S_all      1.0418
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0230P)²+2.3358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0464
_refine_ls_wR_factor_ref         0.0469
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C4(H4a,H4b)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
I1 I 0.244686(12) 0.886756(17) 0.77149(2) 0.02712(7) Uani 1.000000 1 . . .
Se1 Se 0.5 0.55876(3) 0.75 0.01980(9) Uani 1.000000 2 S T P
C1 C 0.48221(17) 0.7736(2) 0.9787(3) 0.0192(4) Uani 1.000000 1 . . .
H1a H 0.43851(17) 0.8391(2) 1.0254(3) 0.0231(5) Uiso 1.000000 1 R . .
H1b H 0.50723(17) 0.7149(2) 1.0740(3) 0.0231(5) Uiso 1.000000 1 R . .
C2 C 0.41706(17) 0.6937(2) 0.8442(3) 0.0172(4) Uani 1.000000 1 . . .
H2 H 0.36460(17) 0.6485(2) 0.9035(3) 0.0207(5) Uiso 1.000000 1 R . .
C3 C 0.36347(16) 0.7628(2) 0.6889(3) 0.0181(4) Uani 1.000000 1 . . .
H3 H 0.32949(16) 0.6945(2) 0.6122(3) 0.0217(5) Uiso 1.000000 1 R . .
C4 C 0.42673(18) 0.8446(2) 0.5804(3) 0.0207(4) Uani 1.000000 1 . . .
H4a H 0.45127(18) 0.9221(2) 0.6474(3) 0.0248(5) Uiso 1.000000 1 R . .
H4b H 0.38303(18) 0.8754(2) 0.4780(3) 0.0248(5) Uiso 1.000000 1 R . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C3 2.192(2) . ?
Se1 C2 1.974(2) 2_656 ?
Se1 C2 1.974(2) . ?
C1 H1a 0.9900 . ?
C1 H1b 0.9900 . ?
C1 C2 1.529(3) . ?
C1 C4 1.537(3) 2_656 ?
C2 H2 1.0000 . ?
C2 C3 1.518(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.522(3) . ?
C4 H4a 0.9900 . ?
C4 H4b 0.9900 . ?

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 Se1 C2 90.54(13) . 2_656 ?
H1b C1 H1a 107.3 . . ?
C2 C1 H1a 108.05(12) . . ?
C2 C1 H1b 108.05(12) . . ?
C4 C1 H1a 108.05(12) 2_656 . ?
C4 C1 H1b 108.05(12) 2_656 . ?
C4 C1 C2 116.98(18) 2_656 . ?
C1 C2 Se1 109.79(15) . 2_656 ?
H2 C2 Se1 107.55(6) . 2_656 ?
H2 C2 C1 107.55(12) . . ?
C3 C2 Se1 105.11(14) . 2_656 ?
C3 C2 C1 118.79(18) . . ?
C3 C2 H2 107.55(12) . . ?
C2 C3 I1 108.93(14) . . ?
H3 C3 I1 107.11(6) . . ?
H3 C3 C2 107.11(12) . . ?
C4 C3 I1 108.14(14) . . ?
C4 C3 C2 117.95(19) . . ?
C4 C3 H3 107.11(12) . . ?
C3 C4 C1 114.61(18) . 2_656 ?
H4a C4 C1 108.61(13) . 2_656 ?
H4a C4 C3 108.61(12) . . ?
H4b C4 C1 108.61(12) . 2_656 ?
H4b C4 C3 108.61(12) . . ?
H4b C4 H4a 107.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1524675'
_audit_update_record             
;
2016-12-27 deposited with the CCDC.
2017-03-29 downloaded from the CCDC.
;
_audit_creation_date             2016-12-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_systematic        
'2,6-dibromo-9-selenabicyclo[3.3.1]nonane diiodine'
_chemical_formula_moiety         'C8 H12 Br2 I2 Se'
_chemical_formula_sum            'C8 H12 Br2 I2 Se'
_chemical_formula_weight         600.76
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.08110 2.30834 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.503(3)
_cell_length_b                   10.107(4)
_cell_length_c                   18.967(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.587(5)
_cell_angle_gamma                90
_cell_volume                     1418.2(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5393
_cell_measurement_temperature    296(2)
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.85
_exptl_absorpt_coefficient_mu    12.598
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.2285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1693 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.3064.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic dark red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.8134
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1075.0188
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15260
_diffrn_reflns_theta_full        28.9984
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.29
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9947
_diffrn_measured_fraction_theta_max 0.9947
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                2914
_reflns_number_total             3749
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.5392
_refine_diff_density_min         -1.6889
_refine_diff_density_rms         0.1848
_refine_ls_d_res_high            0.7330
_refine_ls_d_res_low             8.8915
_refine_ls_goodness_of_fit_ref   1.0100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     117
_refine_ls_number_reflns         3749
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.0100
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0265P)²+2.4243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0745
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C8(H8), C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b), C6(H6a,H6b), C7(H7a,H7b)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
I1 I 0.14662(4) 0.66891(3) 0.477950(14) 0.04544(9) Uani 1.000000 .
I2 I -0.20342(5) 0.69351(4) 0.395312(17) 0.05866(11) Uani 1.000000 .
Br1 Br 0.92891(7) 0.96854(6) 0.60253(4) 0.07145(18) Uani 1.000000 .
Br2 Br 0.32789(7) 0.73009(7) 0.77702(3) 0.06808(17) Uani 1.000000 .
Se1 Se 0.50352(6) 0.63905(5) 0.55780(2) 0.04780(12) Uani 1.000000 .
C1 C 0.6056(6) 0.8202(4) 0.5647(2) 0.0424(9) Uani 1.000000 .
C2 C 0.4775(6) 0.9166(4) 0.5921(2) 0.0442(10) Uani 1.000000 .
C3 C 0.4264(6) 0.8890(4) 0.6655(2) 0.0461(10) Uani 1.000000 .
C4 C 0.3695(6) 0.7475(5) 0.6765(2) 0.0427(9) Uani 1.000000 .
C5 C 0.4975(6) 0.6390(4) 0.6615(2) 0.0435(10) Uani 1.000000 .
C6 C 0.6931(6) 0.6419(5) 0.6995(3) 0.0474(10) Uani 1.000000 .
C7 C 0.8076(6) 0.7631(5) 0.6859(2) 0.0465(10) Uani 1.000000 .
C8 C 0.7946(6) 0.8014(5) 0.6075(2) 0.0452(10) Uani 1.000000 .
H1 H 0.6188(6) 0.8482(4) 0.5164(2) 0.0509(11) Uiso 1.000000 R
H2a H 0.5316(6) 1.0039(4) 0.5935(2) 0.0530(12) Uiso 1.000000 R
H2b H 0.3669(6) 0.9197(4) 0.5574(2) 0.0530(12) Uiso 1.000000 R
H3a H 0.5291(6) 0.9103(4) 0.7020(2) 0.0553(12) Uiso 1.000000 R
H3b H 0.3282(6) 0.9476(4) 0.6722(2) 0.0553(12) Uiso 1.000000 R
H4 H 0.2535(6) 0.7326(5) 0.6451(2) 0.0513(11) Uiso 1.000000 R
H5 H 0.4454(6) 0.5545(4) 0.6731(2) 0.0522(11) Uiso 1.000000 R
H6a H 0.6930(6) 0.6359(5) 0.7505(3) 0.0569(13) Uiso 1.000000 R
H6b H 0.7530(6) 0.5634(5) 0.6856(3) 0.0569(13) Uiso 1.000000 R
H7a H 0.7699(6) 0.8381(5) 0.7118(2) 0.0558(12) Uiso 1.000000 R
H7b H 0.9331(6) 0.7450(5) 0.7054(2) 0.0558(12) Uiso 1.000000 R
H8 H 0.8552(6) 0.7325(5) 0.5838(2) 0.0542(12) Uiso 1.000000 R


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 I2 2.8364(9) . ?
I1 Se1 2.8644(10) . ?
Br1 C8 1.977(5) . ?
Br2 C4 1.991(4) . ?
Se1 C1 1.980(4) . ?
Se1 C5 1.976(5) . ?
C1 C2 1.519(6) . ?
C1 C8 1.524(6) . ?
C2 C3 1.529(6) . ?
C3 C4 1.518(6) . ?
C4 C5 1.515(6) . ?
C5 C6 1.524(6) . ?
C6 C7 1.542(6) . ?
C7 C8 1.525(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
Se1 I1 I2 178.156(16) . . ?
C1 Se1 I1 104.76(13) . . ?
C5 Se1 I1 110.61(13) . . ?
C5 Se1 C1 90.38(18) . . ?
C2 C1 Se1 110.8(3) . . ?
C8 C1 Se1 103.6(3) . . ?
C8 C1 C2 118.9(4) . . ?
C3 C2 C1 117.6(4) . . ?
C4 C3 C2 114.6(4) . . ?
C3 C4 Br2 107.9(3) . . ?
C5 C4 Br2 108.7(3) . . ?
C5 C4 C3 117.0(4) . . ?
C4 C5 Se1 107.8(3) . . ?
C6 C5 Se1 106.9(3) . . ?
C6 C5 C4 119.3(4) . . ?
C7 C6 C5 117.1(4) . . ?
C8 C7 C6 114.7(4) . . ?
C1 C8 Br1 107.7(3) . . ?
C7 C8 Br1 108.2(3) . . ?
C7 C8 C1 116.9(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1524678'
_audit_update_record             
;
2016-12-27 deposited with the CCDC.
2017-03-29 downloaded from the CCDC.
;
_audit_creation_date             2016-12-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_systematic        
'?2,6-dibromo-9-selenabicyclo[3.3.1]nonanebromide pentabromide'
_chemical_formula_moiety         'C8 H12 Br3 Se, 3.5(Br)'
_chemical_formula_sum            'C8 H12 Br6.5 Se'
_chemical_formula_weight         706.52
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.08110 2.30834 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z
3 -x,-y,-z
4 x,-y,z
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z

_symmetry_Int_Tables_number      12
_cell_length_a                   16.440(2)
_cell_length_b                   14.832(2)
_cell_length_c                   13.0060(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.048(2)
_cell_angle_gamma                90
_cell_volume                     3169.3(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3069
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.40
_exptl_absorpt_coefficient_mu    18.730
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.2719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1540 before and 0.0569 after correction.
The Ratio of minimum to maximum transmission is 0.3644.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.9612
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2560.8281
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_av_unetI/netI     0.0861
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19170
_diffrn_reflns_theta_full        28.9997
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.40
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              22
_reflns_limit_h_min              -22
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2968
_reflns_number_total             4359
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.9025
_refine_diff_density_min         -1.8642
_refine_diff_density_rms         0.4346
_refine_ls_d_res_high            0.7330
_refine_ls_d_res_low             8.5018
_refine_ls_goodness_of_fit_ref   0.9910
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     150
_refine_ls_number_reflns         4359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      0.9910
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+3.7111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0825
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C1(H1), C4(H4), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C2(H2a,H2b), C6(H6a,H6b), C3(H3a,H3b)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Se1 Se 0.71321(3) 0.26741(4) 0.30556(4) 0.01647(13) Uani 1.000000 1 . . .
Br2 Br 0.63469(4) 0.23668(4) -0.03404(4) 0.02295(14) Uani 1.000000 1 . . .
Br3 Br 0.73501(3) 0.14562(4) 0.41853(4) 0.01776(13) Uani 1.000000 1 . . .
Br6 Br 0.92950(5) 0.0 0.51097(6) 0.02181(19) Uani 1.000000 2 S T P
Br1 Br 0.43605(4) 0.26097(4) 0.36976(5) 0.02650(15) Uani 1.000000 1 . . .
Br7 Br 0.22141(6) 0.5 0.84152(7) 0.0284(2) Uani 1.000000 2 S T P
Br8 Br 0.28516(5) 0.5 1.03028(6) 0.0232(2) Uani 1.000000 2 S T P
Br9 Br 0.05724(6) 0.5 0.94812(6) 0.0238(2) Uani 1.000000 2 S T P
Br4 Br 0.75418(5) 0.0 0.56993(6) 0.02102(19) Uani 1.000000 2 S T P
Br5 Br 0.56970(6) 0.0 0.52354(8) 0.0314(2) Uani 1.000000 2 S T P
Br10 Br 0.34666(7) 0.5 1.20756(8) 0.0417(3) Uani 1.000000 2 S T P
C7 C 0.5376(4) 0.1573(4) 0.2417(4) 0.0172(12) Uani 1.000000 1 . . .
C2 C 0.5804(3) 0.3724(4) 0.2464(4) 0.0184(13) Uani 1.000000 1 . . .
C5 C 0.6785(3) 0.2051(4) 0.1746(4) 0.0176(12) Uani 1.000000 1 . . .
C1 C 0.5981(3) 0.3014(4) 0.3290(4) 0.0165(12) Uani 1.000000 1 . . .
C6 C 0.6183(4) 0.1294(4) 0.1950(4) 0.0184(13) Uani 1.000000 1 . . .
C4 C 0.6524(3) 0.2857(4) 0.1050(4) 0.0169(12) Uani 1.000000 1 . . .
C8 C 0.5457(3) 0.2179(4) 0.3360(4) 0.0206(13) Uani 1.000000 1 . . .
C3 C 0.5776(4) 0.3382(4) 0.1339(4) 0.0184(13) Uani 1.000000 1 . . .
H7a H 0.5047(4) 0.1882(4) 0.1893(4) 0.0207(15) Uiso 1.000000 1 R . .
H7b H 0.5085(4) 0.1031(4) 0.2605(4) 0.0207(15) Uiso 1.000000 1 R . .
H2a H 0.5284(3) 0.4002(4) 0.2599(4) 0.0221(15) Uiso 1.000000 1 R . .
H2b H 0.6217(3) 0.4189(4) 0.2531(4) 0.0221(15) Uiso 1.000000 1 R . .
H5 H 0.7270(3) 0.1779(4) 0.1457(4) 0.0211(15) Uiso 1.000000 1 R . .
H1 H 0.5971(3) 0.3319(4) 0.3958(4) 0.0199(14) Uiso 1.000000 1 R . .
H6a H 0.6450(4) 0.0861(4) 0.2408(4) 0.0221(15) Uiso 1.000000 1 R . .
H6b H 0.6059(4) 0.0987(4) 0.1304(4) 0.0221(15) Uiso 1.000000 1 R . .
H4 H 0.6982(3) 0.3280(4) 0.1035(4) 0.0203(15) Uiso 1.000000 1 R . .
H8 H 0.5669(3) 0.1815(4) 0.3938(4) 0.0247(16) Uiso 1.000000 1 R . .
H3a H 0.5301(4) 0.3001(4) 0.1233(4) 0.0221(15) Uiso 1.000000 1 R . .
H3b H 0.5713(4) 0.3896(4) 0.0882(4) 0.0221(15) Uiso 1.000000 1 R . .


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
Se1 Br3 2.3479(8) . ?
Se1 C5 2.003(5) . ?
Se1 C1 1.993(5) . ?
Br2 C4 1.962(5) . ?
Br6 Br6 2.3457(18) 2_756 ?
Br1 C8 1.976(6) . ?
Br7 Br8 2.6347(13) . ?
Br8 Br10 2.4844(14) . ?
Br9 Br9 2.3548(18) 2_557 ?
Br5 Br5 2.3509(19) 2_656 ?
C7 C6 1.536(8) . ?
C7 C8 1.522(8) . ?
C2 C1 1.524(8) . ?
C2 C3 1.548(8) . ?
C5 C6 1.526(8) . ?
C5 C4 1.551(8) . ?
C1 C8 1.513(8) . ?
C4 C3 1.514(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 Se1 Br3 102.09(17) . . ?
C1 Se1 Br3 102.91(16) . . ?
C1 Se1 C5 90.2(2) . . ?
Br10 Br8 Br7 179.43(5) . . ?
C8 C7 C6 115.2(5) . . ?
C3 C2 C1 116.1(5) . . ?
C6 C5 Se1 111.0(4) . . ?
C4 C5 Se1 101.8(4) . . ?
C4 C5 C6 120.1(5) . . ?
C2 C1 Se1 103.0(4) . . ?
C8 C1 Se1 110.3(4) . . ?
C8 C1 C2 120.8(5) . . ?
C5 C6 C7 116.5(5) . . ?
C5 C4 Br2 106.3(4) . . ?
C3 C4 Br2 108.9(4) . . ?
C3 C4 C5 117.5(5) . . ?
C7 C8 Br1 108.4(4) . . ?
C1 C8 Br1 105.9(4) . . ?
C1 C8 C7 118.0(5) . . ?
C4 C3 C2 114.0(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1524677'
_audit_update_record             
;
2016-12-27 deposited with the CCDC.
2017-03-29 downloaded from the CCDC.
;
_audit_creation_date             2016-12-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_systematic        
'2,6-diiodo-9-selenabicyclo[3.3.1]nonane diiodine   ?'
_chemical_formula_moiety         'C8 H12 I4 Se'
_chemical_formula_sum            'C8 H12 I4 Se'
_chemical_formula_weight         694.76
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.08110 2.30834 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.7674(8)
_cell_length_b                   10.2154(10)
_cell_length_c                   18.8296(19)
_cell_angle_alpha                90
_cell_angle_beta                 101.236(2)
_cell_angle_gamma                90
_cell_volume                     1465.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4349
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.21
_exptl_absorpt_coefficient_mu    10.953
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0983 before and 0.0440 after correction.
The Ratio of minimum to maximum transmission is 0.7541.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'blackish red'
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.1488
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1217.7445
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17427
_diffrn_reflns_theta_full        30.6031
_diffrn_reflns_theta_max         30.60
_diffrn_reflns_theta_min         2.21
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                3619
_reflns_number_total             4505
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.3361
_refine_diff_density_min         -1.5300
_refine_diff_density_rms         0.2913
_refine_ls_d_res_high            0.6980
_refine_ls_d_res_low             9.2343
_refine_ls_goodness_of_fit_ref   1.0070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     117
_refine_ls_number_reflns         4505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.0070
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0187P)²+0.3881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0475
_refine_ls_wR_factor_ref         0.0512
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C6(H6a,H6b), C3(H3a,H3b), C7(H7a,H7b)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
I1 I 0.35229(3) 0.16374(2) 0.020054(13) 0.02188(6) Uani 1.000000 .
I2 I 0.69949(3) 0.19329(3) 0.101707(14) 0.02666(7) Uani 1.000000 .
I3 I 0.17390(3) 0.23738(3) -0.286611(14) 0.02814(7) Uani 1.000000 .
I4 I -0.43879(3) 0.46643(3) -0.102519(15) 0.02902(7) Uani 1.000000 .
Se1 Se 0.00282(5) 0.13223(4) -0.05877(2) 0.02423(9) Uani 1.000000 .
C1 C -0.1032(5) 0.3097(4) -0.0641(2) 0.0215(8) Uani 1.000000 .
C2 C 0.0176(5) 0.4101(4) -0.0888(2) 0.0200(7) Uani 1.000000 .
C3 C 0.0633(5) 0.3891(3) -0.1636(2) 0.0200(8) Uani 1.000000 .
C4 C 0.1252(5) 0.2514(4) -0.17557(19) 0.0194(7) Uani 1.000000 .
C5 C 0.0075(5) 0.1385(3) -0.1633(2) 0.0207(8) Uani 1.000000 .
C6 C -0.1854(5) 0.1375(4) -0.2029(2) 0.0225(8) Uani 1.000000 .
C7 C -0.3002(5) 0.2519(4) -0.1882(2) 0.0220(8) Uani 1.000000 .
C8 C -0.2869(5) 0.2885(4) -0.1091(2) 0.0208(8) Uani 1.000000 .
H4 H 0.2381(5) 0.2390(4) -0.14253(19) 0.0233(9) Uiso 1.000000 R
H2a H -0.0366(5) 0.4956(4) -0.0885(2) 0.0240(9) Uiso 1.000000 R
H2b H 0.1264(5) 0.4122(4) -0.0533(2) 0.0240(9) Uiso 1.000000 R
H5 H 0.0621(5) 0.0574(3) -0.1758(2) 0.0248(9) Uiso 1.000000 R
H6a H -0.1875(5) 0.1344(4) -0.2545(2) 0.0270(10) Uiso 1.000000 R
H6b H -0.2389(5) 0.0572(4) -0.1901(2) 0.0270(10) Uiso 1.000000 R
H3a H -0.0395(5) 0.4084(3) -0.2004(2) 0.0240(9) Uiso 1.000000 R
H3b H 0.1546(5) 0.4505(3) -0.1697(2) 0.0240(9) Uiso 1.000000 R
H8 H -0.3419(5) 0.2180(4) -0.0861(2) 0.0250(9) Uiso 1.000000 R
H1 H -0.1163(5) 0.3339(4) -0.0151(2) 0.0258(9) Uiso 1.000000 R
H7a H -0.2694(5) 0.3280(4) -0.2139(2) 0.0264(9) Uiso 1.000000 R
H7b H -0.4216(5) 0.2306(4) -0.2084(2) 0.0264(9) Uiso 1.000000 R


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 I2 2.8482(4) . ?
I1 Se1 2.8469(5) . ?
I3 C4 2.201(3) . ?
I4 C8 2.184(4) . ?
Se1 C1 1.985(4) . ?
Se1 C5 1.978(4) . ?
C1 C2 1.523(5) . ?
C1 C8 1.526(5) . ?
C1 H1 0.9800 . ?
C2 C3 1.534(5) . ?
C2 H2a 0.9700 . ?
C2 H2b 0.9700 . ?
C3 C4 1.517(5) . ?
C3 H3a 0.9700 . ?
C3 H3b 0.9700 . ?
C4 C5 1.517(5) . ?
C4 H4 0.9800 . ?
C5 C6 1.538(5) . ?
C5 H5 0.9800 . ?
C6 C7 1.527(5) . ?
C6 H6a 0.9700 . ?
C6 H6b 0.9700 . ?
C7 C8 1.521(5) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C8 H8 0.9800 . ?

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
Se1 I1 I2 178.740(13) . . ?
C1 Se1 I1 105.49(11) . . ?
C5 Se1 I1 108.34(11) . . ?
C5 Se1 C1 90.46(15) . . ?
C2 C1 Se1 110.9(3) . . ?
C8 C1 Se1 103.4(2) . . ?
C8 C1 C2 119.4(3) . . ?
H1 C1 Se1 107.51(11) . . ?
H1 C1 C2 107.51(19) . . ?
H1 C1 C8 107.5(2) . . ?
C3 C2 C1 116.9(3) . . ?
H2a C2 C1 108.1(2) . . ?
H2a C2 C3 108.07(19) . . ?
H2b C2 C1 108.1(2) . . ?
H2b C2 C3 108.07(19) . . ?
H2b C2 H2a 107.3 . . ?
C4 C3 C2 113.7(3) . . ?
H3a C3 C2 108.82(19) . . ?
H3a C3 C4 108.8(2) . . ?
H3b C3 C2 108.82(19) . . ?
H3b C3 C4 108.82(19) . . ?
H3b C3 H3a 107.7 . . ?
C3 C4 I3 108.6(2) . . ?
C5 C4 I3 108.4(2) . . ?
C5 C4 C3 117.7(3) . . ?
H4 C4 I3 107.24(10) . . ?
H4 C4 C3 107.2(2) . . ?
H4 C4 C5 107.24(19) . . ?
C4 C5 Se1 107.7(2) . . ?
C6 C5 Se1 106.0(2) . . ?
C6 C5 C4 119.4(3) . . ?
H5 C5 Se1 107.73(10) . . ?
H5 C5 C4 107.73(19) . . ?
H5 C5 C6 107.73(19) . . ?
C7 C6 C5 117.1(3) . . ?
H6a C6 C5 108.0(2) . . ?
H6a C6 C7 108.0(2) . . ?
H6b C6 C5 108.0(2) . . ?
H6b C6 C7 108.0(2) . . ?
H6b C6 H6a 107.3 . . ?
C8 C7 C6 115.8(3) . . ?
H7a C7 C6 108.3(2) . . ?
H7a C7 C8 108.3(2) . . ?
H7b C7 C6 108.34(19) . . ?
H7b C7 C8 108.3(2) . . ?
H7b C7 H7a 107.4 . . ?
C1 C8 I4 107.9(2) . . ?
C7 C8 I4 109.0(2) . . ?
C7 C8 C1 117.2(3) . . ?
H8 C8 I4 107.44(10) . . ?
H8 C8 C1 107.4(2) . . ?
H8 C8 C7 107.4(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
