# 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 2015

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 751875'
_audit_update_record             
;
2014-04-09 deposited with the CCDC.
2015-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 Br2 Se'
_chemical_formula_sum            'C8 H12 Br2 Se'
_chemical_formula_weight         346.96

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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                   12.7243(10)
_cell_length_b                   10.1559(8)
_cell_length_c                   7.6780(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.9320(17)
_cell_angle_gamma                90.00
_cell_volume                     986.89(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    962
_cell_measurement_theta_min      3
_cell_measurement_theta_max      28

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    11.839
_exptl_absorpt_correction_type   num
_exptl_absorpt_correction_T_min  0.088
_exptl_absorpt_correction_T_max  0.589
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3672
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         28.99
_reflns_number_total             1309
_reflns_number_gt                1135
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0443P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1309
_refine_ls_number_parameters     51
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0690
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.5000 0.44203(4) 0.2500 0.02054(12) Uani 1 2 d S . .
Br1 Br 0.75472(2) 0.11728(3) 0.23426(4) 0.02591(11) Uani 1 1 d . . .
C1 C 0.5882(2) 0.3053(3) 0.1546(3) 0.0202(5) Uani 1 1 d . . .
H1A H 0.6440 0.3512 0.0948 0.024 Uiso 1 1 calc R . .
C2 C 0.6428(2) 0.2355(3) 0.3139(4) 0.0213(5) Uani 1 1 d . . .
H2A H 0.6789 0.3040 0.3922 0.026 Uiso 1 1 calc R . .
C3 C 0.5747(2) 0.1522(3) 0.4243(4) 0.0230(6) Uani 1 1 d . . .
H3A H 0.6193 0.1207 0.5293 0.028 Uiso 1 1 calc R . .
H3B H 0.5494 0.0739 0.3555 0.028 Uiso 1 1 calc R . .
C4 C 0.4786(2) 0.2249(3) 0.4838(3) 0.0214(5) Uani 1 1 d . . .
H4A H 0.4322 0.1589 0.5319 0.026 Uiso 1 1 calc R . .
H4B H 0.5041 0.2848 0.5808 0.026 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se1 0.0223(2) 0.0146(2) 0.0254(2) 0.000 0.00540(15) 0.000
Br1 0.02295(16) 0.02703(19) 0.02780(17) -0.00161(11) 0.00284(12) 0.00636(11)
C1 0.0197(12) 0.0181(12) 0.0232(12) 0.0005(11) 0.0044(10) -0.0001(10)
C2 0.0193(12) 0.0203(14) 0.0242(12) -0.0018(11) 0.0020(10) 0.0022(10)
C3 0.0243(14) 0.0203(14) 0.0240(13) 0.0042(11) 0.0005(11) 0.0015(11)
C4 0.0227(12) 0.0199(13) 0.0217(12) -0.0002(11) 0.0026(10) -0.0017(11)

_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
Se1 C1 1.974(3) . ?
Se1 C1 1.974(3) 2_655 ?
Br1 C2 2.006(3) . ?
C1 C2 1.518(4) . ?
C1 C4 1.527(4) 2_655 ?
C1 H1A 1.0000 . ?
C2 C3 1.528(4) . ?
C2 H2A 1.0000 . ?
C3 C4 1.537(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C1 1.527(4) 2_655 ?
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
C1 Se1 C1 90.56(15) . 2_655 ?
C2 C1 C4 119.1(2) . 2_655 ?
C2 C1 Se1 105.05(17) . . ?
C4 C1 Se1 109.70(17) 2_655 . ?
C2 C1 H1A 107.5 . . ?
C4 C1 H1A 107.5 2_655 . ?
Se1 C1 H1A 107.5 . . ?
C1 C2 C3 117.9(2) . . ?
C1 C2 Br1 108.28(18) . . ?
C3 C2 Br1 107.38(18) . . ?
C1 C2 H2A 107.6 . . ?
C3 C2 H2A 107.6 . . ?
Br1 C2 H2A 107.6 . . ?
C2 C3 C4 114.4(2) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C1 C4 C3 116.9(2) 2_655 . ?
C1 C4 H4A 108.1 2_655 . ?
C3 C4 H4A 108.1 . . ?
C1 C4 H4B 108.1 2_655 . ?
C3 C4 H4B 108.1 . . ?
H4A C4 H4B 107.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 Se1 C1 C2 -65.53(16) 2_655 . . . ?
C1 Se1 C1 C4 63.59(16) 2_655 . . 2_655 ?
C4 C1 C2 C3 -54.9(3) 2_655 . . . ?
Se1 C1 C2 C3 68.4(3) . . . . ?
C4 C1 C2 Br1 67.1(2) 2_655 . . . ?
Se1 C1 C2 Br1 -169.56(12) . . . . ?
C1 C2 C3 C4 -52.6(3) . . . . ?
Br1 C2 C3 C4 -175.12(19) . . . . ?
C2 C3 C4 C1 46.2(3) . . . 2_655 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.136
####################################################################### 
# 
# 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_cl
_database_code_depnum_ccdc_archive 'CCDC 751876'
_audit_update_record             
;
2014-04-09 deposited with the CCDC.
2015-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 Cl2 Se'
_chemical_formula_sum            'C8 H12 Cl2 Se'
_chemical_formula_weight         258.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Orthorombic
_symmetry_space_group_name_H-M   'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'

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

_cell_length_a                   15.5132(15)
_cell_length_b                   7.6193(8)
_cell_length_c                   7.9082(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     934.75(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    177
_cell_measurement_theta_min      3
_cell_measurement_theta_max      29

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.834
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    4.521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.239
_exptl_absorpt_correction_T_max  0.428
_exptl_absorpt_process_details   SADABS


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5930
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         29.58
_reflns_number_total             1402
_reflns_number_gt                1191
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0360P)²+0.5535P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1402
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0664
_refine_ls_wR_factor_gt          0.0632
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.777976(19) 0.2500 0.35660(4) 0.01797(10) Uani 1 2 d S . .
Cl2 Cl 0.82129(5) 0.2500 -0.20481(9) 0.0300(2) Uani 1 2 d S . .
Cl1 Cl 1.06651(5) 0.2500 0.40129(12) 0.0377(2) Uani 1 2 d S . .
C1 C 0.8947(2) 0.1552(6) 0.3671(5) 0.0169(8) Uani 0.50 1 d P . .
H1A H 0.9009 0.0982 0.4747 0.020 Uiso 0.50 1 d PR . .
C6 C 0.8142(3) 0.1890(6) 0.0153(5) 0.0178(8) Uani 0.50 1 d P . .
H6A H 0.7645 0.1149 0.0269 0.021 Uiso 0.50 1 d PR . .
C7 C 0.8934(3) 0.0739(6) 0.0473(6) 0.0209(9) Uani 0.50 1 d P . .
H7A H 0.9438 0.1378 0.0130 0.025 Uiso 0.50 1 d PR . .
H7B H 0.8891 -0.0281 -0.0234 0.025 Uiso 0.50 1 d PR . .
C8 C 0.9052(3) 0.0141(6) 0.2305(6) 0.0199(8) Uani 0.50 1 d P . .
H8A H 0.8644 -0.0778 0.2528 0.024 Uiso 0.50 1 d PR . .
H8B H 0.9618 -0.0357 0.2417 0.024 Uiso 0.50 1 d PR . .
C5 C 0.8000(3) 0.3459(6) 0.1291(5) 0.0155(8) Uani 0.50 1 d P . .
H5A H 0.7486 0.4045 0.0921 0.019 Uiso 0.50 1 d PR . .
C2 C 0.9559(3) 0.3109(6) 0.3655(5) 0.0209(9) Uani 0.50 1 d P . .
H2A H 0.9391 0.3865 0.4569 0.025 Uiso 0.50 1 d PR . .
C3 C 0.9594(3) 0.4246(6) 0.2058(6) 0.0217(9) Uani 0.50 1 d P . .
H3A H 0.9888 0.3603 0.1189 0.026 Uiso 0.50 1 d PR . .
H3B H 0.9929 0.5274 0.2303 0.026 Uiso 0.50 1 d PR . .
C4 C 0.8715(3) 0.4825(6) 0.1394(6) 0.0183(8) Uani 0.50 1 d P . .
H4A H 0.8516 0.5780 0.2084 0.022 Uiso 0.50 1 d PR . .
H4B H 0.8797 0.5279 0.0273 0.022 Uiso 0.50 1 d PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se1 0.01543(15) 0.02317(16) 0.01531(15) 0.000 0.00530(11) 0.000
Cl2 0.0254(4) 0.0517(5) 0.0129(3) 0.000 -0.0023(3) 0.000
Cl1 0.0163(4) 0.0636(7) 0.0333(5) 0.000 -0.0094(3) 0.000
C1 0.0104(18) 0.025(2) 0.0152(18) 0.0021(16) 0.0018(15) 0.0014(16)
C6 0.0145(18) 0.026(2) 0.0130(18) 0.0002(15) -0.0001(15) -0.0025(15)
C7 0.020(2) 0.024(2) 0.019(2) -0.0065(19) -0.0030(17) 0.0016(19)
C8 0.018(2) 0.018(2) 0.024(2) -0.0036(18) -0.001(2) 0.0017(17)
C5 0.0124(17) 0.018(2) 0.0160(19) 0.0016(16) -0.0041(15) -0.0004(15)
C2 0.019(2) 0.028(2) 0.0161(18) -0.0029(15) -0.0024(15) 0.0015(16)
C3 0.017(2) 0.024(2) 0.024(2) -0.0030(18) -0.0025(17) -0.0065(19)
C4 0.0155(19) 0.023(2) 0.017(2) 0.0002(19) 0.0007(19) -0.0040(17)

_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
Se1 C1 1.952(4) . ?
Se1 C5 1.971(4) . ?
Cl2 C6 1.805(4) . ?
Cl1 C2 1.801(4) . ?
C1 C2 1.519(6) . ?
C1 C8 1.533(6) . ?
C1 H1A 0.9600 . ?
C6 C5 1.512(6) . ?
C6 C7 1.531(6) . ?
C6 H6A 0.9600 . ?
C7 C8 1.530(6) . ?
C7 H7A 0.9599 . ?
C7 H7B 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9599 . ?
C5 C4 1.523(6) . ?
C5 H5A 0.9600 . ?
C2 C3 1.533(6) . ?
C2 H2A 0.9600 . ?
C3 C4 1.526(6) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C4 H4A 0.9601 . ?
C4 H4B 0.9599 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Se1 C5 90.85(17) . . ?
C2 C1 C8 118.4(3) . . ?
C2 C1 Se1 106.8(3) . . ?
C8 C1 Se1 109.2(3) . . ?
C2 C1 H1A 107.3 . . ?
C8 C1 H1A 107.3 . . ?
Se1 C1 H1A 107.3 . . ?
C5 C6 C7 118.1(3) . . ?
C5 C6 Cl2 112.3(3) . . ?
C7 C6 Cl2 104.9(3) . . ?
C5 C6 H6A 107.0 . . ?
C7 C6 H6A 107.0 . . ?
Cl2 C6 H6A 107.0 . . ?
C8 C7 C6 115.0(4) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7B 108.6 . . ?
C6 C7 H7B 108.1 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C1 116.5(4) . . ?
C7 C8 H8A 108.2 . . ?
C1 C8 H8A 108.2 . . ?
C7 C8 H8B 108.3 . . ?
C1 C8 H8B 108.0 . . ?
H8A C8 H8B 107.3 . . ?
C6 C5 C4 117.8(4) . . ?
C6 C5 Se1 106.0(3) . . ?
C4 C5 Se1 109.3(3) . . ?
C6 C5 H5A 107.9 . . ?
C4 C5 H5A 107.6 . . ?
Se1 C5 H5A 107.9 . . ?
C1 C2 C3 118.1(3) . . ?
C1 C2 Cl1 113.1(3) . . ?
C3 C2 Cl1 104.0(3) . . ?
C1 C2 H2A 107.1 . . ?
C3 C2 H2A 106.9 . . ?
Cl1 C2 H2A 107.1 . . ?
C4 C3 C2 114.6(4) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3B 108.5 . . ?
C2 C3 H3B 108.3 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 118.1(4) . . ?
C5 C4 H4A 108.3 . . ?
C3 C4 H4A 108.1 . . ?
C5 C4 H4B 107.1 . . ?
C3 C4 H4B 107.7 . . ?
H4A C4 H4B 107.1 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.58
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.485
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 751877'
_audit_update_record             
;
2014-04-09 deposited with the CCDC.
2015-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H24 Cl6 Se3'
_chemical_formula_sum            'C16 H24 Cl6 Se3'
_chemical_formula_weight         665.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   7.5401(5)
_cell_length_b                   11.0902(7)
_cell_length_c                   12.9721(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.3850(15)
_cell_angle_gamma                90.00
_cell_volume                     1084.72(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    159
_cell_measurement_theta_min      3
_cell_measurement_theta_max      29

_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.039
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    5.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.193
_exptl_absorpt_correction_T_max  0.594
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7145
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         29.00
_reflns_number_total             2890
_reflns_number_gt                2473
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0567P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2890
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0858
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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
Se1 Se 0.80515(3) 0.91916(2) 0.07326(2) 0.01307(9) Uani 1 1 d . . .
Se2 Se 0.5000 1.0000 0.0000 0.01285(10) Uani 1 2 d S . .
Cl1 Cl 0.53715(10) 0.58528(6) 0.19246(6) 0.02271(17) Uani 1 1 d . . .
Cl2 Cl 1.20175(9) 0.67682(7) -0.07027(5) 0.02090(16) Uani 1 1 d . . .
Cl3 Cl 0.63671(9) 1.03167(6) -0.16631(5) 0.01815(15) Uani 1 1 d . . .
C1 C 0.7431(3) 0.7811(3) 0.1618(2) 0.0152(5) Uani 1 1 d . . .
H1A H 0.6799 0.8135 0.2235 0.018 Uiso 1 1 calc R . .
C2 C 0.6137(4) 0.7007(2) 0.1032(2) 0.0150(5) Uani 1 1 d . . .
H2A H 0.5088 0.7512 0.0837 0.018 Uiso 1 1 calc R . .
C3 C 0.6786(4) 0.6384(2) 0.0054(2) 0.0156(5) Uani 1 1 d . . .
H3A H 0.5765 0.5981 -0.0285 0.019 Uiso 1 1 calc R . .
H3B H 0.7648 0.5750 0.0252 0.019 Uiso 1 1 calc R . .
C4 C 0.7665(3) 0.7230(2) -0.0729(2) 0.0143(5) Uani 1 1 d . . .
H4A H 0.8218 0.6729 -0.1270 0.017 Uiso 1 1 calc R . .
H4B H 0.6722 0.7715 -0.1065 0.017 Uiso 1 1 calc R . .
C5 C 0.9067(3) 0.8093(2) -0.0311(2) 0.0134(5) Uani 1 1 d . . .
H5A H 0.9485 0.8599 -0.0900 0.016 Uiso 1 1 calc R . .
C6 C 1.0718(3) 0.7585(3) 0.0239(2) 0.0154(5) Uani 1 1 d . . .
H6A H 1.1446 0.8285 0.0480 0.018 Uiso 1 1 calc R . .
C7 C 1.0439(4) 0.6752(3) 0.1165(2) 0.0176(6) Uani 1 1 d . . .
H7A H 1.1606 0.6579 0.1486 0.021 Uiso 1 1 calc R . .
H7B H 0.9942 0.5978 0.0916 0.021 Uiso 1 1 calc R . .
C8 C 0.9199(3) 0.7269(3) 0.1995(2) 0.0182(6) Uani 1 1 d . . .
H8A H 0.8929 0.6618 0.2491 0.022 Uiso 1 1 calc R . .
H8B H 0.9854 0.7903 0.2377 0.022 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se1 0.01355(14) 0.01090(15) 0.01471(15) -0.00105(10) -0.00231(10) 0.00042(9)
Se2 0.01448(18) 0.01033(18) 0.01375(19) -0.00087(14) -0.00004(14) -0.00016(12)
Cl1 0.0249(4) 0.0200(4) 0.0234(4) 0.0066(3) 0.0060(3) -0.0022(3)
Cl2 0.0191(3) 0.0247(4) 0.0189(4) 0.0026(3) 0.0049(3) 0.0071(2)
Cl3 0.0213(3) 0.0171(3) 0.0161(3) -0.0005(3) 0.0024(2) 0.0004(2)
C1 0.0160(12) 0.0185(14) 0.0111(13) 0.0020(11) 0.0000(10) 0.0012(10)
C2 0.0149(12) 0.0137(12) 0.0163(13) 0.0031(11) 0.0013(10) 0.0001(9)
C3 0.0165(12) 0.0121(13) 0.0182(14) -0.0017(11) -0.0003(11) -0.0014(9)
C4 0.0152(12) 0.0138(13) 0.0139(13) -0.0022(11) -0.0024(10) 0.0001(10)
C5 0.0141(12) 0.0114(12) 0.0147(13) 0.0011(10) 0.0012(10) 0.0000(9)
C6 0.0126(12) 0.0170(13) 0.0164(13) -0.0009(11) 0.0010(10) 0.0025(9)
C7 0.0145(12) 0.0232(15) 0.0152(13) 0.0041(12) -0.0002(10) 0.0046(10)
C8 0.0153(12) 0.0241(15) 0.0150(13) 0.0035(12) -0.0024(10) 0.0039(10)

_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
Se1 C1 1.973(3) . ?
Se1 C5 1.979(3) . ?
Se1 Se2 2.6403(3) . ?
Se2 Cl3 2.4228(7) 3_675 ?
Se2 Cl3 2.4228(7) . ?
Se2 Se1 2.6403(3) 3_675 ?
Cl1 C2 1.823(3) . ?
Cl2 C6 1.813(3) . ?
C1 C2 1.522(4) . ?
C1 C8 1.538(4) . ?
C1 H1A 1.0000 . ?
C2 C3 1.528(4) . ?
C2 H2A 1.0000 . ?
C3 C4 1.537(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.523(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.538(4) . ?
C5 H5A 1.0000 . ?
C6 C7 1.531(4) . ?
C6 H6A 1.0000 . ?
C7 C8 1.541(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 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
C1 Se1 C5 90.88(11) . . ?
C1 Se1 Se2 105.29(8) . . ?
C5 Se1 Se2 107.64(8) . . ?
Cl3 Se2 Cl3 180.00(3) 3_675 . ?
Cl3 Se2 Se1 90.298(18) 3_675 . ?
Cl3 Se2 Se1 89.702(18) . . ?
Cl3 Se2 Se1 89.702(18) 3_675 3_675 ?
Cl3 Se2 Se1 90.298(18) . 3_675 ?
Se1 Se2 Se1 180.0 . 3_675 ?
C2 C1 C8 118.8(2) . . ?
C2 C1 Se1 108.49(18) . . ?
C8 C1 Se1 106.23(18) . . ?
C2 C1 H1A 107.6 . . ?
C8 C1 H1A 107.6 . . ?
Se1 C1 H1A 107.6 . . ?
C1 C2 C3 118.2(2) . . ?
C1 C2 Cl1 107.34(19) . . ?
C3 C2 Cl1 108.33(19) . . ?
C1 C2 H2A 107.5 . . ?
C3 C2 H2A 107.5 . . ?
Cl1 C2 H2A 107.5 . . ?
C2 C3 C4 114.5(2) . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 C3 116.8(2) . . ?
C5 C4 H4A 108.1 . . ?
C3 C4 H4A 108.1 . . ?
C5 C4 H4B 108.1 . . ?
C3 C4 H4B 108.1 . . ?
H4A C4 H4B 107.3 . . ?
C4 C5 C6 119.5(2) . . ?
C4 C5 Se1 111.05(17) . . ?
C6 C5 Se1 102.94(18) . . ?
C4 C5 H5A 107.6 . . ?
C6 C5 H5A 107.6 . . ?
Se1 C5 H5A 107.6 . . ?
C7 C6 C5 118.1(2) . . ?
C7 C6 Cl2 107.78(19) . . ?
C5 C6 Cl2 108.03(19) . . ?
C7 C6 H6A 107.5 . . ?
C5 C6 H6A 107.5 . . ?
Cl2 C6 H6A 107.5 . . ?
C6 C7 C8 114.2(2) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C1 C8 C7 116.9(2) . . ?
C1 C8 H8A 108.1 . . ?
C7 C8 H8A 108.1 . . ?
C1 C8 H8B 108.1 . . ?
C7 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 Se1 Se2 Cl3 40.21(9) . . . 3_675 ?
C5 Se1 Se2 Cl3 136.16(8) . . . 3_675 ?
C1 Se1 Se2 Cl3 -139.79(9) . . . . ?
C5 Se1 Se2 Cl3 -43.84(8) . . . . ?
C5 Se1 C1 C2 -61.14(19) . . . . ?
Se2 Se1 C1 C2 47.42(18) . . . . ?
C5 Se1 C1 C8 67.59(19) . . . . ?
Se2 Se1 C1 C8 176.16(16) . . . . ?
C8 C1 C2 C3 -56.9(3) . . . . ?
Se1 C1 C2 C3 64.4(3) . . . . ?
C8 C1 C2 Cl1 65.9(3) . . . . ?
Se1 C1 C2 Cl1 -172.82(12) . . . . ?
C1 C2 C3 C4 -51.4(3) . . . . ?
Cl1 C2 C3 C4 -173.62(19) . . . . ?
C2 C3 C4 C5 48.3(3) . . . . ?
C3 C4 C5 C6 58.9(3) . . . . ?
C3 C4 C5 Se1 -60.7(3) . . . . ?
C1 Se1 C5 C4 61.0(2) . . . . ?
Se2 Se1 C5 C4 -45.4(2) . . . . ?
C1 Se1 C5 C6 -68.04(18) . . . . ?
Se2 Se1 C5 C6 -174.40(14) . . . . ?
C4 C5 C6 C7 -55.9(3) . . . . ?
Se1 C5 C6 C7 67.6(3) . . . . ?
C4 C5 C6 Cl2 66.6(3) . . . . ?
Se1 C5 C6 Cl2 -169.83(13) . . . . ?
C5 C6 C7 C8 -51.7(3) . . . . ?
Cl2 C6 C7 C8 -174.3(2) . . . . ?
C2 C1 C8 C7 59.7(3) . . . . ?
Se1 C1 C8 C7 -62.8(3) . . . . ?
C6 C7 C8 C1 47.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.139
_refine_diff_density_min         -0.973
