# 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 2019

####################################################################### 
# 
# 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_compound_7
_database_code_depnum_ccdc_archive 'CCDC 1893457'
loop_
_audit_author_name
_audit_author_address
'Borodina Tatiana'
;A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Science
Russia
;
_audit_update_record             
;
2019-01-25 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_formula_moiety         'C11 H13 Br O2 Se'
_chemical_formula_sum            'C11 H13 Br O2 Se'
_chemical_formula_weight         336.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   'Cc   '

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'

_cell_length_a                   9.4516(4)
_cell_length_b                   17.5281(6)
_cell_length_c                   8.3971(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.8310(10)
_cell_angle_gamma                90.00
_cell_volume                     1218.70(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9701
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.91

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    6.338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2991
_exptl_absorpt_correction_T_max  0.6653
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20079
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         30.10
_reflns_number_total             3144
_reflns_number_gt                2510
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 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)+(0.0538P)²+0.0565P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(11)
_refine_ls_number_reflns         3144
_refine_ls_number_parameters     138
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.158
_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
Br1 Br -0.15431(7) 0.72352(3) -0.48058(6) 0.07219(19) Uani 1 1 d . . .
Se1 Se -0.21633(6) 0.63565(3) 0.00433(6) 0.05605(15) Uani 1 1 d . . .
O2 O 0.3808(4) 0.61395(19) 0.5754(4) 0.0511(7) Uani 1 1 d . . .
O1 O 0.4970(4) 0.5685(2) 0.3711(4) 0.0530(7) Uani 1 1 d . . .
C10 C -0.1676(7) 0.7146(2) -0.2534(7) 0.0529(11) Uani 1 1 d . . .
H10A H -0.0657 0.7331 -0.1500 0.063 Uiso 1 1 calc R . .
H10B H -0.2567 0.7471 -0.2619 0.063 Uiso 1 1 calc R . .
C2 C -0.1967(6) 0.6331(2) -0.2194(6) 0.0446(9) Uani 1 1 d . . .
H2 H -0.2997 0.6141 -0.3233 0.054 Uiso 1 1 calc R . .
C8 C 0.0095(5) 0.6142(2) 0.1344(5) 0.0376(7) Uani 1 1 d . . .
C7 C 0.1083(5) 0.6226(2) 0.3203(5) 0.0386(8) Uani 1 1 d . . .
H7 H 0.0650 0.6397 0.3952 0.046 Uiso 1 1 calc R . .
C6 C 0.2700(5) 0.6057(2) 0.3946(5) 0.0357(7) Uani 1 1 d . . .
C12 C 0.3207(7) 0.6369(3) 0.6926(6) 0.0653(14) Uani 1 1 d . . .
H12A H 0.2717 0.6876 0.6567 0.098 Uiso 1 1 calc R . .
H12C H 0.4095 0.6387 0.8178 0.098 Uiso 1 1 calc R . .
H12B H 0.2392 0.6003 0.6846 0.098 Uiso 1 1 calc R . .
C5 C 0.3344(4) 0.5816(2) 0.2833(5) 0.0370(8) Uani 1 1 d . . .
C11 C 0.5736(6) 0.5590(3) 0.2619(7) 0.0556(11) Uani 1 1 d . . .
H11B H 0.5283 0.5143 0.1833 0.083 Uiso 1 1 calc R . .
H11C H 0.6899 0.5516 0.3406 0.083 Uiso 1 1 calc R . .
H11A H 0.5554 0.6045 0.1866 0.083 Uiso 1 1 calc R . .
C4 C 0.2335(5) 0.57272(19) 0.0982(5) 0.0374(7) Uani 1 1 d . . .
H4 H 0.2765 0.5553 0.0232 0.045 Uiso 1 1 calc R . .
C9 C 0.0700(5) 0.58906(18) 0.0218(5) 0.0353(7) Uani 1 1 d . . .
C3 C -0.0553(5) 0.5765(2) -0.1835(7) 0.0495(10) Uani 1 1 d . . .
H3B H -0.0941 0.5231 -0.2060 0.059 Uiso 1 1 calc R . .
H3A H -0.0072 0.5888 -0.2622 0.059 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
Br1 0.1071(5) 0.0632(3) 0.0639(3) 0.0150(2) 0.0553(3) 0.0108(3)
Se1 0.03353(19) 0.0921(3) 0.0458(2) 0.0035(2) 0.02173(16) 0.0019(2)
O2 0.0447(17) 0.0757(19) 0.0298(13) -0.0046(12) 0.0154(13) 0.0079(14)
O1 0.0404(15) 0.0814(19) 0.0376(15) 0.0020(13) 0.0191(12) 0.0143(14)
C10 0.060(3) 0.052(2) 0.048(3) 0.0027(17) 0.027(2) 0.0115(19)
C2 0.035(2) 0.058(2) 0.037(2) -0.0046(16) 0.0153(17) -0.0046(16)
C8 0.0340(18) 0.0431(18) 0.0363(17) 0.0039(14) 0.0173(15) 0.0008(14)
C7 0.037(2) 0.0491(19) 0.0365(19) 0.0012(15) 0.0229(17) 0.0033(15)
C6 0.0392(19) 0.0405(17) 0.0307(16) 0.0001(13) 0.0194(15) 0.0017(14)
C12 0.065(3) 0.100(4) 0.027(2) -0.010(2) 0.019(2) 0.017(3)
C5 0.0382(19) 0.0424(19) 0.0307(17) 0.0042(13) 0.0168(15) 0.0078(14)
C11 0.045(2) 0.072(3) 0.057(3) -0.015(2) 0.031(2) 0.006(2)
C4 0.0420(19) 0.0402(17) 0.0328(17) -0.0031(13) 0.0202(15) 0.0045(14)
C9 0.0386(18) 0.0363(15) 0.0289(16) -0.0005(13) 0.0148(14) 0.0008(13)
C3 0.0303(19) 0.055(2) 0.055(2) 0.0200(18) 0.0141(18) 0.0079(16)

_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
Br1 C10 1.977(5) . ?
Se1 C8 1.908(4) . ?
Se1 C2 1.976(5) . ?
O2 C6 1.374(5) . ?
O2 C12 1.411(6) . ?
O1 C5 1.365(5) . ?
O1 C11 1.427(6) . ?
C10 C2 1.509(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C2 C3 1.571(6) . ?
C2 H2 1.0000 . ?
C8 C7 1.388(5) . ?
C8 C9 1.392(5) . ?
C7 C6 1.376(6) . ?
C7 H7 0.9500 . ?
C6 C5 1.404(5) . ?
C12 H12A 0.9800 . ?
C12 H12C 0.9800 . ?
C12 H12B 0.9800 . ?
C5 C4 1.386(5) . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 H11A 0.9800 . ?
C4 C9 1.387(6) . ?
C4 H4 0.9500 . ?
C9 C3 1.566(6) . ?
C3 H3B 0.9900 . ?
C3 H3A 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
C8 Se1 C2 87.00(17) . . ?
C6 O2 C12 116.9(4) . . ?
C5 O1 C11 117.4(3) . . ?
C2 C10 Br1 111.1(3) . . ?
C2 C10 H10A 109.4 . . ?
Br1 C10 H10A 109.4 . . ?
C2 C10 H10B 109.4 . . ?
Br1 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C2 C3 114.7(4) . . ?
C10 C2 Se1 105.5(3) . . ?
C3 C2 Se1 107.0(3) . . ?
C10 C2 H2 109.8 . . ?
C3 C2 H2 109.8 . . ?
Se1 C2 H2 109.8 . . ?
C7 C8 C9 121.6(4) . . ?
C7 C8 Se1 125.7(3) . . ?
C9 C8 Se1 112.7(3) . . ?
C6 C7 C8 119.0(4) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
O2 C6 C7 124.5(3) . . ?
O2 C6 C5 115.0(3) . . ?
C7 C6 C5 120.4(3) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12C C12 H12B 109.5 . . ?
O1 C5 C4 125.0(3) . . ?
O1 C5 C6 115.3(3) . . ?
C4 C5 C6 119.7(3) . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C11 H11A 109.5 . . ?
H11B C11 H11A 109.5 . . ?
H11C C11 H11A 109.5 . . ?
C5 C4 C9 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C9 C4 H4 119.8 . . ?
C4 C9 C8 118.8(3) . . ?
C4 C9 C3 124.3(3) . . ?
C8 C9 C3 116.8(3) . . ?
C9 C3 C2 104.2(4) . . ?
C9 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C9 C3 H3A 110.9 . . ?
C2 C3 H3A 110.9 . . ?
H3B C3 H3A 108.9 . . ?

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
Br1 C10 C2 C3 64.9(4) . . . . ?
Br1 C10 C2 Se1 -177.5(3) . . . . ?
C8 Se1 C2 C10 -93.2(3) . . . . ?
C8 Se1 C2 C3 29.4(3) . . . . ?
C2 Se1 C8 C7 164.6(3) . . . . ?
C2 Se1 C8 C9 -14.6(3) . . . . ?
C9 C8 C7 C6 0.1(5) . . . . ?
Se1 C8 C7 C6 -179.1(3) . . . . ?
C12 O2 C6 C7 4.0(6) . . . . ?
C12 O2 C6 C5 -178.9(4) . . . . ?
C8 C7 C6 O2 177.9(4) . . . . ?
C8 C7 C6 C5 1.0(5) . . . . ?
C11 O1 C5 C4 12.3(6) . . . . ?
C11 O1 C5 C6 -167.7(4) . . . . ?
O2 C6 C5 O1 1.1(5) . . . . ?
C7 C6 C5 O1 178.3(4) . . . . ?
O2 C6 C5 C4 -178.9(3) . . . . ?
C7 C6 C5 C4 -1.7(5) . . . . ?
O1 C5 C4 C9 -178.7(3) . . . . ?
C6 C5 C4 C9 1.3(6) . . . . ?
C5 C4 C9 C8 -0.3(5) . . . . ?
C5 C4 C9 C3 -176.4(3) . . . . ?
C7 C8 C9 C4 -0.5(5) . . . . ?
Se1 C8 C9 C4 178.8(3) . . . . ?
C7 C8 C9 C3 176.0(3) . . . . ?
Se1 C8 C9 C3 -4.8(4) . . . . ?
C4 C9 C3 C2 -156.6(4) . . . . ?
C8 C9 C3 C2 27.2(4) . . . . ?
C10 C2 C3 C9 81.0(4) . . . . ?
Se1 C2 C3 C9 -35.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.10
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.963
_refine_diff_density_min         -0.933
_refine_diff_density_rms         0.348
####################################################################### 
# 
# 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_compound_8
_database_code_depnum_ccdc_archive 'CCDC 1893458'
loop_
_audit_author_name
_audit_author_address
'Borodina Tatiana'
;A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Science
Russia
;
_audit_update_record             
;
2019-01-25 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;
_audit_creation_date             2019-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_formula_moiety         'C11.57 H15.55 O2.59 Se, 0.41(C), 0.41(O)'
_chemical_formula_sum            'C11.98 H15.55 O3 Se'
_chemical_formula_weight         286.54
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_cell_length_a                   12.3669(6)
_cell_length_b                   6.1164(3)
_cell_length_c                   15.6194(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.018(2)
_cell_angle_gamma                90.00
_cell_volume                     1181.28(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9263
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      2.61
_cell_measurement_theta_min      30.06
_exptl_absorpt_coefficient_mu    3.168
_exptl_absorpt_correction_T_max  0.0320
_exptl_absorpt_correction_T_min  0.0051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1342 before and 0.0783 after correction. The Ratio of minimum to maximum transmission is 0.1594. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.673
_exptl_crystal_size_mid          0.673
_exptl_crystal_size_min          0.472
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            40146
_diffrn_reflns_theta_full        30.08
_diffrn_reflns_theta_max         30.08
_diffrn_reflns_theta_min         2.61
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_number_gt                3278
_reflns_number_total             3473
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3473
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0286P)²+1.5397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0734
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Se1-C2 \\sim Se1-C2A
 with sigma of 0.02
 O3-C10 \\sim O3A-C10
 with sigma of 0.02
 O3-C13 \\sim O3A-C13
 with sigma of 0.02
 C3-C2 \\sim C3-C2A
 with sigma of 0.02
 C10-C2 \\sim C10-C2A
 with sigma of 0.02
3. Others
 Sof(C3)=Sof(H3a)=Sof(H3b)=Sof(C10)=Sof(H10a)=Sof(H10b)=Sof(C13)=Sof(H13a)=
 Sof(H13b)=Sof(H13c)=FVAR(1)
 Sof(C2A)=Sof(O3A)=1-FVAR(2)
 Sof(O3)=Sof(C2)=Sof(H2)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C2(H2)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C10(H10a,H10b)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4)
4.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C11(H11a,H11b,H11c), C13(H13a,H13b,H13c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Se1 Se 0.432951(14) 0.20987(3) 0.413838(12) 0.01860(7) Uani 1 d A 1 D
O2 O 0.86060(11) 0.0563(2) 0.38877(9) 0.0233(3) Uani 1 d A 1 .
O1 O 0.88598(11) 0.4069(2) 0.29744(10) 0.0232(3) Uani 1 d A 1 .
O3 O 0.2114(2) 0.4471(4) 0.3826(3) 0.0220(7) Uani 0.590(8) d A 1 D
C8 C 0.58009(14) 0.2602(3) 0.38413(11) 0.0160(3) Uani 1 d . . .
C7 C 0.66662(14) 0.1183(3) 0.40026(11) 0.0176(3) Uani 1 d A . .
H7 H 0.6556 -0.0161 0.4293 0.021 Uiso 1 calc . . R
C6 C 0.76901(15) 0.1769(3) 0.37316(12) 0.0173(3) Uani 1 d . . .
C12 C 0.85321(17) -0.1083(4) 0.45329(14) 0.0258(4) Uani 1 d . . .
H12A H 0.8236 -0.0442 0.5054 0.039 Uiso 1 calc A . GR
H12B H 0.9254 -0.1677 0.4659 0.039 Uiso 1 calc A . GR
H12C H 0.8056 -0.2260 0.4328 0.039 Uiso 1 calc A . GR
C5 C 0.78360(14) 0.3709(3) 0.32611(11) 0.0174(3) Uani 1 d A . .
C11 C 0.90008(16) 0.5916(3) 0.24225(14) 0.0249(4) Uani 1 d . . .
H11A H 0.8489 0.5819 0.1938 0.037 Uiso 1 calc A . GR
H11B H 0.9742 0.5927 0.2210 0.037 Uiso 1 calc A . GR
H11C H 0.8868 0.7265 0.2743 0.037 Uiso 1 calc A . GR
C4 C 0.69690(14) 0.5117(3) 0.31261(12) 0.0182(3) Uani 1 d . . .
H4 H 0.7072 0.6447 0.2824 0.022 Uiso 1 calc A . R
C9 C 0.59449(14) 0.4590(3) 0.34319(11) 0.0165(3) Uani 1 d A . .
C3 C 0.49659(16) 0.6019(3) 0.33581(15) 0.0265(5) Uani 0.994(5) d A 1 D
H3A H 0.5002 0.7163 0.3806 0.032 Uiso 0.994(5) calc A 1 R
H3B H 0.4954 0.6753 0.2793 0.032 Uiso 0.994(5) calc A 1 R
C10 C 0.29890(16) 0.5857(4) 0.37628(16) 0.0278(5) Uani 0.994(5) d A 1 D
H10A H 0.3151 0.6503 0.4332 0.033 Uiso 0.994(5) calc A 1 R
H10B H 0.2801 0.7065 0.3365 0.033 Uiso 0.994(5) calc A 1 R
C13 C 0.11563(16) 0.5560(4) 0.41027(16) 0.0294(5) Uani 0.994(5) d A 1 D
H13A H 0.1234 0.5931 0.4711 0.044 Uiso 0.994(5) calc A 1 GR
H13B H 0.0531 0.4593 0.4019 0.044 Uiso 0.994(5) calc A 1 GR
H13C H 0.1048 0.6899 0.3768 0.044 Uiso 0.994(5) calc A 1 GR
C2 C 0.3959(2) 0.4728(5) 0.3454(2) 0.0182(9) Uani 0.590(8) d A 1 D
H2 H 0.3765 0.4182 0.2868 0.022 Uiso 0.590(8) calc A 1 R
C2A C 0.4084(3) 0.5297(8) 0.3932(3) 0.0188(12) Uani 0.410(8) d A 2 D
O3A O 0.2236(3) 0.4985(10) 0.4280(4) 0.0333(15) Uani 0.410(8) d A 2 D

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 0.01398(9) 0.02192(10) 0.01999(10) 0.00481(7) 0.00245(6) -0.00214(6)
O2 0.0176(6) 0.0239(7) 0.0286(7) 0.0060(6) 0.0039(5) 0.0047(5)
O1 0.0153(6) 0.0237(7) 0.0308(7) 0.0052(6) 0.0084(5) -0.0004(5)
O3 0.0132(11) 0.0244(12) 0.0285(19) -0.0028(11) 0.0005(10) -0.0010(9)
C8 0.0148(7) 0.0189(8) 0.0143(7) 0.0007(6) 0.0017(6) -0.0019(6)
C7 0.0174(8) 0.0189(8) 0.0166(8) 0.0027(6) 0.0012(6) -0.0007(6)
C6 0.0161(8) 0.0181(8) 0.0177(8) -0.0008(6) 0.0012(6) 0.0012(6)
C12 0.0241(9) 0.0248(10) 0.0286(10) 0.0063(8) -0.0015(7) 0.0052(8)
C5 0.0143(7) 0.0203(8) 0.0179(8) -0.0007(6) 0.0031(6) -0.0021(6)
C11 0.0214(9) 0.0239(9) 0.0296(10) 0.0043(8) 0.0101(7) -0.0038(7)
C4 0.0169(8) 0.0175(8) 0.0202(8) 0.0029(6) 0.0035(6) -0.0008(6)
C9 0.0157(7) 0.0177(8) 0.0161(8) -0.0002(6) 0.0010(6) -0.0006(6)
C3 0.0182(9) 0.0215(9) 0.0402(12) 0.0113(8) 0.0081(8) 0.0038(7)
C10 0.0168(9) 0.0232(10) 0.0437(13) 0.0051(9) 0.0073(8) 0.0023(7)
C13 0.0142(9) 0.0318(11) 0.0423(12) 0.0058(9) 0.0026(8) 0.0038(8)
C2 0.0158(14) 0.0222(15) 0.0164(19) 0.0015(13) -0.0019(11) 0.0006(11)
C2A 0.015(2) 0.025(2) 0.016(3) 0.0002(19) 0.0027(16) -0.0021(17)
O3A 0.0147(17) 0.050(3) 0.036(3) 0.019(3) 0.0053(17) 0.0031(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 C8 1.9109(18) . ?
Se1 C2 1.980(3) . ?
O2 C6 1.370(2) . ?
O2 C12 1.429(2) . ?
O1 C5 1.368(2) . ?
O1 C11 1.434(2) . ?
O3 C10 1.379(3) . ?
O3 C13 1.433(3) . ?
C8 C7 1.397(2) . ?
C8 C9 1.387(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.389(2) . ?
C6 C5 1.409(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C5 C4 1.388(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C4 H4 0.9500 . ?
C4 C9 1.399(2) . ?
C9 C3 1.496(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.485(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C2 1.472(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C2 H2 1.0000 . ?

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
C8 Se1 C2 87.16(10) . . ?
C6 O2 C12 116.23(15) . . ?
C5 O1 C11 116.52(15) . . ?
C10 O3 C13 112.9(2) . . ?
C7 C8 Se1 125.85(13) . . ?
C9 C8 Se1 112.57(13) . . ?
C9 C8 C7 121.58(16) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 C8 118.94(17) . . ?
C6 C7 H7 120.5 . . ?
O2 C6 C7 124.20(17) . . ?
O2 C6 C5 115.67(16) . . ?
C7 C6 C5 120.13(17) . . ?
O1 C5 C6 115.70(16) . . ?
O1 C5 C4 124.57(17) . . ?
C4 C5 C6 119.72(16) . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C9 120.45(17) . . ?
C9 C4 H4 119.8 . . ?
C8 C9 C4 118.93(17) . . ?
C8 C9 C3 115.94(16) . . ?
C4 C9 C3 125.13(17) . . ?
C9 C3 H3A 109.4 . . ?
C9 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C2 C3 C9 111.14(19) . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
O3 C10 H10A 109.1 . . ?
O3 C10 H10B 109.1 . . ?
O3 C10 C2 112.3(2) . . ?
H10A C10 H10B 107.9 . . ?
C2 C10 H10A 109.1 . . ?
C2 C10 H10B 109.1 . . ?
Se1 C2 H2 105.8 . . ?
C3 C2 Se1 107.45(18) . . ?
C3 C2 H2 105.8 . . ?
C10 C2 Se1 112.7(2) . . ?
C10 C2 C3 118.2(3) . . ?
C10 C2 H2 105.8 . . ?

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
Se1 C8 C7 C6 178.82(14) . . . . ?
Se1 C8 C9 C4 -175.85(14) . . . . ?
Se1 C8 C9 C3 4.4(2) . . . . ?
O2 C6 C5 O1 4.0(2) . . . . ?
O2 C6 C5 C4 -175.30(17) . . . . ?
O1 C5 C4 C9 178.87(17) . . . . ?
O3 C10 C2 Se1 -53.3(4) . . . . ?
O3 C10 C2 C3 -179.8(3) . . . . ?
C8 Se1 C2 C3 -19.2(2) . . . . ?
C8 Se1 C2 C10 -151.3(2) . . . . ?
C8 C7 C6 O2 176.84(17) . . . . ?
C8 C7 C6 C5 -3.4(3) . . . . ?
C8 C9 C3 C2 -20.5(3) . . . . ?
C7 C8 C9 C4 4.1(3) . . . . ?
C7 C8 C9 C3 -175.64(18) . . . . ?
C7 C6 C5 O1 -175.78(16) . . . . ?
C7 C6 C5 C4 4.9(3) . . . . ?
C6 C5 C4 C9 -1.9(3) . . . . ?
C12 O2 C6 C7 -15.4(3) . . . . ?
C12 O2 C6 C5 164.84(17) . . . . ?
C5 C4 C9 C8 -2.6(3) . . . . ?
C5 C4 C9 C3 177.19(19) . . . . ?
C11 O1 C5 C6 173.90(17) . . . . ?
C11 O1 C5 C4 -6.8(3) . . . . ?
C4 C9 C3 C2 159.7(2) . . . . ?
C9 C8 C7 C6 -1.1(3) . . . . ?
C9 C3 C2 Se1 25.4(3) . . . . ?
C9 C3 C2 C10 154.4(2) . . . . ?
C13 O3 C10 C2 -178.4(2) . . . . ?
C2 Se1 C8 C7 -171.2(2) . . . . ?
C2 Se1 C8 C9 8.75(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
