# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_aaa
_database_code_depnum_ccdc_archive 'CCDC 1985689'
loop_
_audit_author_name
_audit_author_address
'Ruili Guo'
;Northwest University
China
;
_audit_update_record             
;
2020-02-22 deposited with the CCDC.	2020-06-24 downloaded from the CCDC.
;
_audit_creation_date             2020-01-06
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H5 Br F2 O Se'
_chemical_formula_sum            'C8 H5 Br F2 O Se'
_chemical_formula_weight         313.99
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.062(5)
_cell_length_b                   7.902(7)
_cell_length_c                   10.845(9)
_cell_angle_alpha                105.988(13)
_cell_angle_beta                 93.472(15)
_cell_angle_gamma                92.468(13)
_cell_volume                     497.5(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    899
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.76
_cell_measurement_theta_min      3.37
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.775
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.3545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1412 before and 0.0385 after correction. The Ratio of minimum to maximum transmission is 0.4756. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.096
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2671
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         1.959
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1358
_reflns_number_total             1933
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.613
_refine_diff_density_min         -1.480
_refine_diff_density_rms         0.248
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1933
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0623
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1113P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1580
_refine_ls_wR_factor_ref         0.1755
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 Se01-C004 \\sim Se01-C00C
 with sigma of 0.002
3. Rigid bond restraints
 C00C, C004
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C004) = Uanis(C00C)
5. Rigid body (RIGU) restrains
 C004, C00C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: H00B(0.5) H00C(0.5) F0AA(0.5) F2(0.5) F3(0.5) F4(0.5)
7.a Ternary CH refined with riding coordinates:
 C00C(H00B), C00C(H00C)
7.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C006(H006), C008(H008), C00A(H00A)
7.c Fitted hexagon refined as free rotating group:
 C005(C009,C006,C007,C008,C00A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se01 Se 0.43714(13) 0.76014(12) 0.87842(7) 0.0688(4) Uani 1 1 d D . . . .
Br02 Br 0.78513(14) 0.80380(10) 0.25924(7) 0.0685(3) Uani 1 1 d . . . . .
O003 O 0.0827(8) 0.6465(8) 0.6959(5) 0.0731(16) Uani 1 1 d . . . . .
C004 C 0.2734(11) 0.7020(9) 0.7090(5) 0.0560(12) Uani 1 1 d D U . . .
C005 C 0.4019(6) 0.7304(5) 0.6032(3) 0.0407(13) Uani 1 1 d . . . . .
C009 C 0.6133(6) 0.8131(5) 0.6250(3) 0.0484(15) Uani 1 1 d G . . . .
H009 H 0.6791 0.8536 0.7084 0.058 Uiso 1 1 calc R . . . .
C006 C 0.7264(5) 0.8353(5) 0.5223(4) 0.0515(16) Uani 1 1 d G . . . .
H006 H 0.8678 0.8907 0.5369 0.062 Uiso 1 1 calc R . . . .
C007 C 0.6280(7) 0.7748(5) 0.3977(3) 0.0483(16) Uani 1 1 d G . . . .
C008 C 0.4166(7) 0.6920(5) 0.3758(3) 0.0512(16) Uani 1 1 d G . . . .
H008 H 0.3508 0.6515 0.2924 0.061 Uiso 1 1 calc R . . . .
C00A C 0.3035(5) 0.6698(5) 0.4786(4) 0.0462(15) Uani 1 1 d G . . . .
H00A H 0.1621 0.6145 0.4639 0.055 Uiso 1 1 calc R . . . .
C00C C 0.1824(11) 0.7035(10) 0.9661(6) 0.0560(12) Uani 1 1 d D U . . .
H00B H 0.0914 0.6100 0.9028 0.067 Uiso 0.5 1 calc R . P A 2
H00C H 0.0446 0.6721 0.9106 0.067 Uiso 0.5 1 calc R . P B 1
F0AA F 0.061(3) 0.829(3) 1.003(2) 0.142(8) Uani 0.5 1 d . . P C 2
F2 F 0.170(3) 0.849(3) 1.0733(14) 0.114(7) Uani 0.5 1 d . . P C 1
F3 F 0.245(4) 0.638(4) 1.058(2) 0.129(11) Uani 0.5 1 d . . P C 2
F4 F 0.236(7) 0.581(4) 1.028(3) 0.125(10) Uani 0.5 1 d . . P C 1


_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
Se01 C004 1.961(5) . ?
Se01 C00C 1.960(5) . ?
Br02 C007 1.886(3) . ?
O003 C004 1.205(8) . ?
C004 C005 1.487(7) . ?
C005 C009 1.3900 . ?
C005 C00A 1.3900 . ?
C009 H009 0.9300 . ?
C009 C006 1.3900 . ?
C006 H006 0.9300 . ?
C006 C007 1.3900 . ?
C007 C008 1.3900 . ?
C008 H008 0.9300 . ?
C008 C00A 1.3900 . ?
C00A H00A 0.9300 . ?
C00C H00B 0.9800 . ?
C00C H00C 0.9800 . ?
C00C F0AA 1.25(2) . ?
C00C F2 1.403(18) . ?
C00C F3 1.29(2) . ?
C00C F4 1.36(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00C Se01 C004 94.1(3) . . ?
O003 C004 Se01 120.3(5) . . ?
O003 C004 C005 124.4(5) . . ?
C005 C004 Se01 115.2(4) . . ?
C009 C005 C004 122.4(3) . . ?
C009 C005 C00A 120.0 . . ?
C00A C005 C004 117.6(3) . . ?
C005 C009 H009 120.0 . . ?
C005 C009 C006 120.0 . . ?
C006 C009 H009 120.0 . . ?
C009 C006 H006 120.0 . . ?
C009 C006 C007 120.0 . . ?
C007 C006 H006 120.0 . . ?
C006 C007 Br02 119.4(2) . . ?
C006 C007 C008 120.0 . . ?
C008 C007 Br02 120.6(2) . . ?
C007 C008 H008 120.0 . . ?
C007 C008 C00A 120.0 . . ?
C00A C008 H008 120.0 . . ?
C005 C00A H00A 120.0 . . ?
C008 C00A C005 120.0 . . ?
C008 C00A H00A 120.0 . . ?
Se01 C00C H00B 106.5 . . ?
Se01 C00C H00C 113.9 . . ?
F0AA C00C Se01 113.7(11) . . ?
F0AA C00C H00B 106.5 . . ?
F0AA C00C F3 112.4(18) . . ?
F2 C00C Se01 105.5(8) . . ?
F2 C00C H00C 113.9 . . ?
F3 C00C Se01 110.7(12) . . ?
F3 C00C H00B 106.5 . . ?
F4 C00C Se01 109.5(17) . . ?
F4 C00C H00C 113.9 . . ?
F4 C00C F2 98.9(15) . . ?

_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_a
_database_code_depnum_ccdc_archive 'CCDC 1985690'
loop_
_audit_author_name
_audit_author_address
'Ruili Guo'
;Northwest University
China
;
_audit_update_record             
;
2020-02-22 deposited with the CCDC.	2020-06-24 downloaded from the CCDC.
;
_audit_creation_date             2020-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.25(C18 H13 F2 O3 S Se)'
_chemical_formula_sum            'C4.50 H3.25 F0.50 O0.75 S0.25 Se0.25'
_chemical_formula_weight         106.58
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.167(3)
_cell_length_b                   9.361(4)
_cell_length_c                   12.114(5)
_cell_angle_alpha                97.388(6)
_cell_angle_beta                 97.162(7)
_cell_angle_gamma                106.374(6)
_cell_volume                     868.5(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2418
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.82
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.316
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5428
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0610 before and 0.0298 after correction.
The Ratio of minimum to maximum transmission is 0.7283.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       bulk
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4612
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.932
_diffrn_reflns_theta_min         2.302
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2726
_reflns_number_total             3286
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.816
_refine_diff_density_min         -1.072
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0984P)²+0.5560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1552
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00M(H00M)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00N(H00N), C00O(H00O)
2.c Idealised Me refined as rotating group:
 C00P(H00B,H00D,H00E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se01 Se 0.25197(8) 0.29040(5) 0.21974(4) 0.0705(2) Uani 1 1 d . . . . .
S002 S 0.21089(11) 0.05487(9) 0.63017(7) 0.0357(2) Uani 1 1 d . . . . .
O003 O 0.0733(3) 0.0325(3) 0.6944(3) 0.0493(7) Uani 1 1 d . . . . .
O004 O 0.2026(4) -0.0535(3) 0.5331(2) 0.0484(6) Uani 1 1 d . . . . .
C005 C 0.2243(4) 0.2163(3) 0.5798(3) 0.0260(6) Uani 1 1 d . . . . .
O006 O 0.3345(5) 0.5748(3) 0.3504(3) 0.0739(10) Uani 1 1 d . . . . .
F007 F 0.2031(5) 0.4870(4) 0.0801(3) 0.1037(12) Uani 1 1 d . . . . .
C008 C 0.2629(5) 0.3790(4) 0.4580(3) 0.0393(8) Uani 1 1 d . . . . .
C009 C 0.4070(4) 0.0904(4) 0.7227(3) 0.0349(7) Uani 1 1 d . . . . .
C00A C 0.5566(5) 0.0916(4) 0.6778(3) 0.0414(8) Uani 1 1 d . . . . .
H00A H 0.554144 0.077991 0.600155 0.050 Uiso 1 1 calc R . . . .
C00B C 0.2146(5) 0.3537(4) 0.6382(3) 0.0396(8) Uani 1 1 d . . . . .
C00C C 0.2548(5) 0.2352(4) 0.4727(3) 0.0385(8) Uani 1 1 d . . . . .
H00C H 0.267962 0.161233 0.418467 0.046 Uiso 1 1 calc R . . . .
C00D C 0.2381(5) 0.4582(4) 0.5629(3) 0.0406(8) Uani 1 1 d . . . . .
C00E C 0.2926(5) 0.4428(4) 0.3556(3) 0.0472(9) Uani 1 1 d . . . . .
F00F F 0.3755(7) 0.3684(5) 0.0341(3) 0.1281(16) Uani 1 1 d . . . . .
C00G C 0.4104(5) 0.1126(5) 0.8382(3) 0.0477(9) Uani 1 1 d . . . . .
H00G H 0.310118 0.112778 0.867040 0.057 Uiso 1 1 calc R . . . .
C00H C 0.7146(5) 0.1330(5) 0.8672(4) 0.0498(10) Uani 1 1 d . . . . .
C00I C 0.7097(5) 0.1136(5) 0.7520(4) 0.0483(9) Uani 1 1 d . . . . .
H00I H 0.810463 0.115350 0.723226 0.058 Uiso 1 1 calc R . . . .
C00J C 0.1851(6) 0.3905(5) 0.7466(4) 0.0512(10) Uani 1 1 d . . . . .
H00J H 0.169314 0.319966 0.794912 0.061 Uiso 1 1 calc R . . . .
C00K C 0.5634(6) 0.1344(5) 0.9105(4) 0.0543(10) Uani 1 1 d . . . . .
H00K H 0.566218 0.150129 0.988162 0.065 Uiso 1 1 calc R . . . .
C00L C 0.2308(7) 0.6034(5) 0.5984(4) 0.0599(11) Uani 1 1 d . . . . .
H00L H 0.246012 0.674239 0.550373 0.072 Uiso 1 1 calc R . . . .
C00M C 0.3317(7) 0.4383(6) 0.1242(4) 0.0684(13) Uani 1 1 d . . . . .
H00M H 0.429666 0.522996 0.165631 0.082 Uiso 1 1 calc R . . . .
C00N C 0.2005(8) 0.6401(5) 0.7062(5) 0.0740(15) Uani 1 1 d . . . . .
H00N H 0.193620 0.736399 0.730135 0.089 Uiso 1 1 calc R . . . .
C00O C 0.1797(8) 0.5359(6) 0.7808(4) 0.0691(13) Uani 1 1 d . . . . .
H00O H 0.162265 0.564642 0.853738 0.083 Uiso 1 1 calc R . . . .
C00P C 0.8805(7) 0.1539(7) 0.9462(5) 0.0791(16) Uani 1 1 d . . . . .
H00B H 0.931259 0.077160 0.921351 0.119 Uiso 1 1 calc GR . . . .
H00D H 0.856337 0.146133 1.021090 0.119 Uiso 1 1 calc GR . . . .
H00E H 0.959628 0.251737 0.946401 0.119 Uiso 1 1 calc GR . . . .


_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
Se01 C00E 1.961(4) . ?
Se01 C00M 1.942(5) . ?
S002 O003 1.428(3) . ?
S002 O004 1.432(3) . ?
S002 C005 1.682(3) . ?
S002 C009 1.758(4) . ?
C005 C00B 1.413(5) . ?
C005 C00C 1.376(5) . ?
O006 C00E 1.198(5) . ?
F007 C00M 1.337(7) . ?
C008 C00C 1.364(5) . ?
C008 C00D 1.453(5) . ?
C008 C00E 1.462(5) . ?
C009 C00A 1.396(5) . ?
C009 C00G 1.383(5) . ?
C00A C00I 1.392(5) . ?
C00B C00D 1.412(5) . ?
C00B C00J 1.382(6) . ?
C00D C00L 1.392(6) . ?
F00F C00M 1.340(6) . ?
C00G C00K 1.381(6) . ?
C00H C00I 1.378(6) . ?
C00H C00K 1.403(6) . ?
C00H C00P 1.506(6) . ?
C00J C00O 1.386(6) . ?
C00L C00N 1.377(7) . ?
C00N C00O 1.403(7) . ?

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
C00M Se01 C00E 94.08(19) . . ?
O003 S002 O004 120.58(18) . . ?
O003 S002 C005 106.77(16) . . ?
O003 S002 C009 108.55(17) . . ?
O004 S002 C005 104.53(16) . . ?
O004 S002 C009 109.94(17) . . ?
C005 S002 C009 105.36(15) . . ?
C00B C005 S002 127.4(3) . . ?
C00C C005 S002 123.5(2) . . ?
C00C C005 C00B 109.0(3) . . ?
C00C C008 C00D 107.7(3) . . ?
C00C C008 C00E 126.3(3) . . ?
C00D C008 C00E 126.0(3) . . ?
C00A C009 S002 119.0(3) . . ?
C00G C009 S002 119.9(3) . . ?
C00G C009 C00A 121.0(3) . . ?
C00I C00A C009 118.5(3) . . ?
C00D C00B C005 107.0(3) . . ?
C00J C00B C005 130.6(3) . . ?
C00J C00B C00D 122.3(3) . . ?
C008 C00C C005 109.7(3) . . ?
C00B C00D C008 106.5(3) . . ?
C00L C00D C008 134.4(4) . . ?
C00L C00D C00B 119.1(4) . . ?
O006 C00E Se01 120.8(3) . . ?
O006 C00E C008 125.3(4) . . ?
C008 C00E Se01 113.9(3) . . ?
C00K C00G C009 119.7(4) . . ?
C00I C00H C00K 119.3(4) . . ?
C00I C00H C00P 120.6(4) . . ?
C00K C00H C00P 120.1(4) . . ?
C00H C00I C00A 121.3(4) . . ?
C00B C00J C00O 117.8(4) . . ?
C00G C00K C00H 120.3(4) . . ?
C00N C00L C00D 118.7(4) . . ?
F007 C00M Se01 111.4(4) . . ?
F007 C00M F00F 103.9(4) . . ?
F00F C00M Se01 108.1(4) . . ?
C00L C00N C00O 121.7(4) . . ?
C00J C00O C00N 120.4(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
