# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_ja
_database_code_depnum_ccdc_archive 'CCDC 1899043'
loop_
_audit_author_name
_audit_author_address
'yuchun li'
;Nanning Normal University
China
;
_audit_update_record             
;
2019-02-23 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.33 H3 N0.33 O0.33 Se0.33'
_chemical_formula_weight         79.38

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   5.4632(4)
_cell_length_b                   16.8139(11)
_cell_length_c                   10.7302(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.574(2)
_cell_angle_gamma                90.00
_cell_volume                     974.64(11)
_cell_formula_units_Z            12
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2238
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      27.52

_exptl_crystal_description       BAR
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    3.810
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16605
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.52
_reflns_number_total             2238
_reflns_number_gt                1520
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0371P)²+0.3263P] 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         2238
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.47487(6) 0.41242(2) 0.87067(3) 0.05119(15) Uani 1 1 d . . .
C10 C 0.4506(6) 0.59583(17) 0.6047(3) 0.0394(7) Uani 1 1 d . . .
C9 C 0.4062(5) 0.52762(19) 0.6855(3) 0.0418(7) Uani 1 1 d . . .
O1 O 0.2082(4) 0.49226(14) 0.6730(2) 0.0631(7) Uani 1 1 d . . .
C8 C 0.7611(7) 0.39648(19) 0.9825(3) 0.0534(9) Uani 1 1 d . . .
C7 C 0.6092(5) 0.50118(18) 0.7853(3) 0.0453(8) Uani 1 1 d . . .
H7A H 0.6586 0.5441 0.8442 0.054 Uiso 1 1 calc R . .
H7B H 0.7522 0.4843 0.7483 0.054 Uiso 1 1 calc R . .
C6 C 0.7017(6) 0.70381(19) 0.5525(3) 0.0502(8) Uani 1 1 d . . .
H6A H 0.8454 0.7341 0.5687 0.060 Uiso 1 1 calc R . .
C5 C 0.3076(6) 0.67878(19) 0.4246(3) 0.0432(7) Uani 1 1 d . . .
C4 C 0.6675(5) 0.64097(19) 0.6291(3) 0.0442(8) Uani 1 1 d . . .
H4A H 0.7878 0.6284 0.6970 0.053 Uiso 1 1 calc R . .
C3 C 0.2735(5) 0.61569(19) 0.5025(3) 0.0412(7) Uani 1 1 d . . .
H3A H 0.1289 0.5858 0.4864 0.049 Uiso 1 1 calc R . .
C2 C 0.5244(6) 0.72258(19) 0.4512(3) 0.0471(8) Uani 1 1 d . . .
H2A H 0.5507 0.7654 0.3998 0.057 Uiso 1 1 calc R . .
C1 C 0.1156(6) 0.7009(2) 0.3141(3) 0.0567(9) Uani 1 1 d . . .
H1A H -0.0232 0.6656 0.3102 0.085 Uiso 1 1 calc R . .
H1B H 0.1862 0.6968 0.2376 0.085 Uiso 1 1 calc R . .
H1C H 0.0617 0.7546 0.3241 0.085 Uiso 1 1 calc R . .
N1 N 0.9356(7) 0.3849(2) 1.0527(3) 0.0791(10) Uani 1 1 d . . .


_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 1.843(4) . ?
Se1 C7 1.950(3) . ?
C10 C3 1.391(4) . ?
C10 C4 1.398(4) . ?
C10 C9 1.479(4) . ?
C9 O1 1.224(3) . ?
C9 C7 1.490(4) . ?
C8 N1 1.140(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 C4 1.369(4) . ?
C6 C2 1.380(4) . ?
C6 H6A 0.9300 . ?
C5 C2 1.388(4) . ?
C5 C3 1.381(4) . ?
C5 C1 1.508(4) . ?
C4 H4A 0.9300 . ?
C3 H3A 0.9300 . ?
C2 H2A 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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 C7 94.30(13) . . ?
C3 C10 C4 119.2(3) . . ?
C3 C10 C9 119.5(3) . . ?
C4 C10 C9 121.3(3) . . ?
O1 C9 C10 122.1(3) . . ?
O1 C9 C7 119.0(3) . . ?
C10 C9 C7 118.9(3) . . ?
N1 C8 Se1 178.3(3) . . ?
C9 C7 Se1 105.9(2) . . ?
C9 C7 H7A 110.6 . . ?
Se1 C7 H7A 110.6 . . ?
C9 C7 H7B 110.6 . . ?
Se1 C7 H7B 110.6 . . ?
H7A C7 H7B 108.7 . . ?
C4 C6 C2 120.4(3) . . ?
C4 C6 H6A 119.8 . . ?
C2 C6 H6A 119.8 . . ?
C2 C5 C3 118.1(3) . . ?
C2 C5 C1 120.2(3) . . ?
C3 C5 C1 121.7(3) . . ?
C6 C4 C10 119.6(3) . . ?
C6 C4 H4A 120.2 . . ?
C10 C4 H4A 120.2 . . ?
C5 C3 C10 121.4(3) . . ?
C5 C3 H3A 119.3 . . ?
C10 C3 H3A 119.3 . . ?
C5 C2 C6 121.2(3) . . ?
C5 C2 H2A 119.4 . . ?
C6 C2 H2A 119.4 . . ?
C5 C1 H1A 109.5 . . ?
C5 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C5 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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
C3 C10 C9 O1 -7.1(4) . . . . ?
C4 C10 C9 O1 172.8(3) . . . . ?
C3 C10 C9 C7 173.0(3) . . . . ?
C4 C10 C9 C7 -7.1(4) . . . . ?
C7 Se1 C8 N1 -172(13) . . . . ?
O1 C9 C7 Se1 -0.9(4) . . . . ?
C10 C9 C7 Se1 179.1(2) . . . . ?
C8 Se1 C7 C9 -179.7(2) . . . . ?
C2 C6 C4 C10 -0.3(5) . . . . ?
C3 C10 C4 C6 0.1(4) . . . . ?
C9 C10 C4 C6 -179.8(3) . . . . ?
C2 C5 C3 C10 -0.3(4) . . . . ?
C1 C5 C3 C10 -179.6(3) . . . . ?
C4 C10 C3 C5 0.2(4) . . . . ?
C9 C10 C3 C5 -179.9(3) . . . . ?
C3 C5 C2 C6 0.1(4) . . . . ?
C1 C5 C2 C6 179.4(3) . . . . ?
C4 C6 C2 C5 0.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_ja_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1899044'
loop_
_audit_author_name
_audit_author_address
'yuchun li'
;Nanning Normal University
China
;
_audit_update_record             
;
2019-02-23 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.43 H4.71 N0.14 O0.43 Se0.14'
_chemical_formula_weight         66.07

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   10.1323(6)
_cell_length_b                   7.4394(5)
_cell_length_c                   15.4852(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.787(2)
_cell_angle_gamma                90.00
_cell_volume                     1146.62(13)
_cell_formula_units_Z            14
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5088
_cell_measurement_theta_min      3.55
_cell_measurement_theta_max      27.55

_exptl_crystal_description       BAR
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    1.661
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18097
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.55
_reflns_number_total             5088
_reflns_number_gt                4061
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0367P)²+0.1772P] 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   0.014(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5088
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0786
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.87132(3) 0.19343(5) 0.595022(18) 0.05885(11) Uani 1 1 d . . .
C21 C 0.73591(19) -0.3046(4) 0.90789(13) 0.0309(4) Uani 1 1 d . . .
H21A H 0.6393 -0.3249 0.8890 0.037 Uiso 1 1 calc R . .
C20 C 0.7642(2) -0.3234(4) 1.00751(13) 0.0283(5) Uani 1 1 d . . .
H20A H 0.8605 -0.3047 1.0290 0.034 Uiso 1 1 calc R . .
O1 O 0.7515(3) 0.1547(3) 0.73481(15) 0.0727(7) Uani 1 1 d . . .
C19 C 0.7214(3) -0.1831(4) 1.15078(17) 0.0322(6) Uani 1 1 d . . .
C28 C 0.6110(2) -0.2991(5) 1.30837(14) 0.0431(5) Uani 1 1 d . . .
H28A H 0.5251 -0.3499 1.2789 0.052 Uiso 1 1 calc R . .
C18 C 0.6714(3) 0.0153(4) 0.90982(17) 0.0403(6) Uani 1 1 d . . .
H18A H 0.5785 -0.0154 0.8866 0.048 Uiso 1 1 calc R . .
H18B H 0.6874 0.1360 0.8904 0.048 Uiso 1 1 calc R . .
C17 C 0.6959(3) 0.0103(3) 1.01028(18) 0.0409(6) Uani 1 1 d . . .
H17A H 0.6312 0.0884 1.0304 0.049 Uiso 1 1 calc R . .
H17B H 0.7848 0.0581 1.0328 0.049 Uiso 1 1 calc R . .
C16 C 0.8379(4) -0.0417(4) 0.6425(2) 0.0569(8) Uani 1 1 d . . .
H16A H 0.7786 -0.1127 0.5991 0.068 Uiso 1 1 calc R . .
H16B H 0.9214 -0.1069 0.6608 0.068 Uiso 1 1 calc R . .
C15 C 0.7639(2) -0.1167(3) 0.87459(16) 0.0321(5) Uani 1 1 d . . .
C14 C 0.8584(3) -0.0958(4) 1.18590(18) 0.0478(7) Uani 1 1 d . . .
H14A H 0.8768 -0.1010 1.2490 0.072 Uiso 1 1 calc R . .
H14B H 0.8568 0.0274 1.1673 0.072 Uiso 1 1 calc R . .
H14C H 0.9272 -0.1593 1.1634 0.072 Uiso 1 1 calc R . .
C13 C 0.7243(2) -0.3764(3) 1.18352(17) 0.0335(6) Uani 1 1 d . . .
C12 C 0.7349(3) -0.1517(4) 0.77447(16) 0.0396(6) Uani 1 1 d . . .
H12A H 0.6372 -0.1651 0.7575 0.047 Uiso 1 1 calc R . .
C11 C 0.9111(3) -0.0598(4) 0.90263(19) 0.0489(7) Uani 1 1 d . . .
H11A H 0.9678 -0.1445 0.8803 0.073 Uiso 1 1 calc R . .
H11B H 0.9341 -0.0567 0.9656 0.073 Uiso 1 1 calc R . .
H11C H 0.9234 0.0575 0.8795 0.073 Uiso 1 1 calc R . .
C10 C 0.8050(4) -0.4323(4) 0.85417(19) 0.0511(8) Uani 1 1 d . . .
H10A H 0.7600 -0.5479 0.8477 0.061 Uiso 1 1 calc R . .
H10B H 0.8982 -0.4503 0.8818 0.061 Uiso 1 1 calc R . .
C9 C 0.9503(5) 0.1115(5) 0.5054(3) 0.0863(13) Uani 1 1 d . . .
O3 O 0.62084(17) -0.3105(5) 1.40314(9) 0.0506(4) Uani 1 1 d . . .
C8 C 0.6854(2) -0.1790(3) 1.04911(16) 0.0301(5) Uani 1 1 d . . .
H8A H 0.5905 -0.2131 1.0336 0.036 Uiso 1 1 calc R . .
C27 C 0.5692(3) -0.4582(4) 1.43363(19) 0.0497(7) Uani 1 1 d . . .
C7 C 0.7252(3) -0.5165(4) 1.13208(18) 0.0388(6) Uani 1 1 d . . .
H7A H 0.7248 -0.6297 1.1575 0.047 Uiso 1 1 calc R . .
O4 O 0.5152(3) -0.5745(4) 1.38711(15) 0.0821(8) Uani 1 1 d . . .
C5 C 0.7732(3) -0.0015(4) 0.71956(17) 0.0441(6) Uani 1 1 d . . .
N1 N 0.9996(7) 0.0774(6) 0.4475(4) 0.152(2) Uani 1 1 d . . .
C3 C 0.7949(4) -0.3394(4) 0.76483(17) 0.0573(8) Uani 1 1 d . . .
H3A H 0.7373 -0.4076 0.7193 0.069 Uiso 1 1 calc R . .
H3B H 0.8831 -0.3289 0.7494 0.069 Uiso 1 1 calc R . .
C1 C 0.7268(3) -0.5081(4) 1.03566(17) 0.0371(6) Uani 1 1 d . . .
H1A H 0.6387 -0.5401 1.0030 0.044 Uiso 1 1 calc R . .
H1B H 0.7908 -0.5953 1.0216 0.044 Uiso 1 1 calc R . .
C24 C 0.6165(3) -0.1016(4) 1.28588(19) 0.0506(7) Uani 1 1 d . . .
H24A H 0.6989 -0.0491 1.3178 0.061 Uiso 1 1 calc R . .
H24B H 0.5413 -0.0391 1.3029 0.061 Uiso 1 1 calc R . .
C29 C 0.5899(4) -0.4567(5) 1.5308(2) 0.0670(10) Uani 1 1 d . . .
H29A H 0.5523 -0.5638 1.5509 0.101 Uiso 1 1 calc R . .
H29B H 0.5465 -0.3532 1.5499 0.101 Uiso 1 1 calc R . .
H29C H 0.6844 -0.4519 1.5547 0.101 Uiso 1 1 calc R . .
C23 C 0.6106(3) -0.0808(4) 1.18738(18) 0.0433(6) Uani 1 1 d . . .
H23A H 0.6171 0.0460 1.1742 0.052 Uiso 1 1 calc R . .
H23B H 0.5236 -0.1226 1.1568 0.052 Uiso 1 1 calc R . .
C22 C 0.7251(3) -0.4005(4) 1.28050(18) 0.0436(6) Uani 1 1 d . . .
H22A H 0.7173 -0.5274 1.2932 0.052 Uiso 1 1 calc R . .
H22B H 0.8099 -0.3577 1.3140 0.052 Uiso 1 1 calc R . .


_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 C9 1.831(4) . ?
Se1 C16 1.951(3) . ?
C21 C10 1.517(4) . ?
C21 C20 1.522(3) . ?
C21 C15 1.535(4) . ?
C21 H21A 0.9800 . ?
C20 C1 1.511(4) . ?
C20 C8 1.549(3) . ?
C20 H20A 0.9800 . ?
O1 C5 1.214(4) . ?
C19 C13 1.523(4) . ?
C19 C14 1.537(4) . ?
C19 C8 1.548(4) . ?
C19 C23 1.549(4) . ?
C28 O3 1.455(2) . ?
C28 C22 1.510(4) . ?
C28 C24 1.514(5) . ?
C28 H28A 0.9800 . ?
C18 C15 1.528(4) . ?
C18 C17 1.529(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C17 C8 1.543(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C16 C5 1.495(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C15 C11 1.532(4) . ?
C15 C12 1.545(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 C7 1.313(4) . ?
C13 C22 1.511(4) . ?
C12 C5 1.499(4) . ?
C12 C3 1.541(4) . ?
C12 H12A 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C10 C3 1.533(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 N1 1.135(5) . ?
O3 C27 1.341(5) . ?
C8 H8A 0.9800 . ?
C27 O4 1.191(4) . ?
C27 C29 1.480(4) . ?
C7 C1 1.498(4) . ?
C7 H7A 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C24 C23 1.523(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?

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
C9 Se1 C16 96.80(15) . . ?
C10 C21 C20 118.7(2) . . ?
C10 C21 C15 104.6(2) . . ?
C20 C21 C15 114.4(2) . . ?
C10 C21 H21A 106.1 . . ?
C20 C21 H21A 106.1 . . ?
C15 C21 H21A 106.1 . . ?
C1 C20 C21 111.5(2) . . ?
C1 C20 C8 109.5(2) . . ?
C21 C20 C8 110.1(2) . . ?
C1 C20 H20A 108.6 . . ?
C21 C20 H20A 108.6 . . ?
C8 C20 H20A 108.6 . . ?
C13 C19 C14 108.7(2) . . ?
C13 C19 C8 110.1(2) . . ?
C14 C19 C8 112.1(2) . . ?
C13 C19 C23 108.2(2) . . ?
C14 C19 C23 109.4(2) . . ?
C8 C19 C23 108.3(2) . . ?
O3 C28 C22 110.4(2) . . ?
O3 C28 C24 106.9(3) . . ?
C22 C28 C24 110.9(2) . . ?
O3 C28 H28A 109.6 . . ?
C22 C28 H28A 109.6 . . ?
C24 C28 H28A 109.6 . . ?
C15 C18 C17 110.7(2) . . ?
C15 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C18 C17 C8 114.1(2) . . ?
C18 C17 H17A 108.7 . . ?
C8 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C8 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C5 C16 Se1 104.7(2) . . ?
C5 C16 H16A 110.8 . . ?
Se1 C16 H16A 110.8 . . ?
C5 C16 H16B 110.8 . . ?
Se1 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?
C18 C15 C11 110.5(2) . . ?
C18 C15 C21 107.5(2) . . ?
C11 C15 C21 112.8(2) . . ?
C18 C15 C12 116.9(2) . . ?
C11 C15 C12 108.9(2) . . ?
C21 C15 C12 99.84(19) . . ?
C19 C14 H14A 109.5 . . ?
C19 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C19 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C13 C22 120.6(2) . . ?
C7 C13 C19 123.3(2) . . ?
C22 C13 C19 116.1(2) . . ?
C5 C12 C3 118.1(2) . . ?
C5 C12 C15 115.0(2) . . ?
C3 C12 C15 104.2(2) . . ?
C5 C12 H12A 106.2 . . ?
C3 C12 H12A 106.2 . . ?
C15 C12 H12A 106.2 . . ?
C15 C11 H11A 109.5 . . ?
C15 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C15 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C21 C10 C3 104.6(2) . . ?
C21 C10 H10A 110.8 . . ?
C3 C10 H10A 110.8 . . ?
C21 C10 H10B 110.8 . . ?
C3 C10 H10B 110.8 . . ?
H10A C10 H10B 108.9 . . ?
N1 C9 Se1 173.5(4) . . ?
C27 O3 C28 116.5(3) . . ?
C17 C8 C20 113.1(2) . . ?
C17 C8 C19 113.2(2) . . ?
C20 C8 C19 111.6(2) . . ?
C17 C8 H8A 106.1 . . ?
C20 C8 H8A 106.1 . . ?
C19 C8 H8A 106.1 . . ?
O4 C27 O3 123.2(3) . . ?
O4 C27 C29 125.6(3) . . ?
O3 C27 C29 111.2(3) . . ?
C13 C7 C1 125.1(3) . . ?
C13 C7 H7A 117.5 . . ?
C1 C7 H7A 117.5 . . ?
O1 C5 C16 118.0(3) . . ?
O1 C5 C12 121.9(3) . . ?
C16 C5 C12 120.2(3) . . ?
C10 C3 C12 106.4(2) . . ?
C10 C3 H3A 110.5 . . ?
C12 C3 H3A 110.5 . . ?
C10 C3 H3B 110.5 . . ?
C12 C3 H3B 110.5 . . ?
H3A C3 H3B 108.6 . . ?
C7 C1 C20 112.1(2) . . ?
C7 C1 H1A 109.2 . . ?
C20 C1 H1A 109.2 . . ?
C7 C1 H1B 109.2 . . ?
C20 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C28 C24 C23 109.4(2) . . ?
C28 C24 H24A 109.8 . . ?
C23 C24 H24A 109.8 . . ?
C28 C24 H24B 109.8 . . ?
C23 C24 H24B 109.8 . . ?
H24A C24 H24B 108.2 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C24 C23 C19 114.9(2) . . ?
C24 C23 H23A 108.5 . . ?
C19 C23 H23A 108.5 . . ?
C24 C23 H23B 108.5 . . ?
C19 C23 H23B 108.5 . . ?
H23A C23 H23B 107.5 . . ?
C28 C22 C13 111.2(2) . . ?
C28 C22 H22A 109.4 . . ?
C13 C22 H22A 109.4 . . ?
C28 C22 H22B 109.4 . . ?
C13 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?

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
C10 C21 C20 C1 -59.0(3) . . . . ?
C15 C21 C20 C1 176.67(19) . . . . ?
C10 C21 C20 C8 179.2(2) . . . . ?
C15 C21 C20 C8 54.9(2) . . . . ?
C15 C18 C17 C8 -54.1(3) . . . . ?
C9 Se1 C16 C5 179.3(2) . . . . ?
C17 C18 C15 C11 -65.0(3) . . . . ?
C17 C18 C15 C21 58.6(3) . . . . ?
C17 C18 C15 C12 169.7(2) . . . . ?
C10 C21 C15 C18 167.1(2) . . . . ?
C20 C21 C15 C18 -61.4(2) . . . . ?
C10 C21 C15 C11 -70.8(3) . . . . ?
C20 C21 C15 C11 60.7(3) . . . . ?
C10 C21 C15 C12 44.7(2) . . . . ?
C20 C21 C15 C12 176.13(18) . . . . ?
C14 C19 C13 C7 -109.6(3) . . . . ?
C8 C19 C13 C7 13.6(4) . . . . ?
C23 C19 C13 C7 131.7(3) . . . . ?
C14 C19 C13 C22 70.8(3) . . . . ?
C8 C19 C13 C22 -166.0(2) . . . . ?
C23 C19 C13 C22 -47.9(3) . . . . ?
C18 C15 C12 C5 73.8(3) . . . . ?
C11 C15 C12 C5 -52.4(3) . . . . ?
C21 C15 C12 C5 -170.7(2) . . . . ?
C18 C15 C12 C3 -155.4(2) . . . . ?
C11 C15 C12 C3 78.5(3) . . . . ?
C21 C15 C12 C3 -39.9(3) . . . . ?
C20 C21 C10 C3 -161.1(2) . . . . ?
C15 C21 C10 C3 -32.1(3) . . . . ?
C16 Se1 C9 N1 176(5) . . . . ?
C22 C28 O3 C27 -83.6(3) . . . . ?
C24 C28 O3 C27 155.8(3) . . . . ?
C18 C17 C8 C20 47.4(3) . . . . ?
C18 C17 C8 C19 175.6(2) . . . . ?
C1 C20 C8 C17 -168.9(2) . . . . ?
C21 C20 C8 C17 -46.0(3) . . . . ?
C1 C20 C8 C19 62.1(3) . . . . ?
C21 C20 C8 C19 -175.0(2) . . . . ?
C13 C19 C8 C17 -173.6(2) . . . . ?
C14 C19 C8 C17 -52.4(3) . . . . ?
C23 C19 C8 C17 68.4(3) . . . . ?
C13 C19 C8 C20 -44.6(3) . . . . ?
C14 C19 C8 C20 76.5(3) . . . . ?
C23 C19 C8 C20 -162.7(2) . . . . ?
C28 O3 C27 O4 -1.5(5) . . . . ?
C28 O3 C27 C29 177.9(3) . . . . ?
C22 C13 C7 C1 -178.9(2) . . . . ?
C19 C13 C7 C1 1.5(4) . . . . ?
Se1 C16 C5 O1 2.3(4) . . . . ?
Se1 C16 C5 C12 -178.8(2) . . . . ?
C3 C12 C5 O1 -165.8(3) . . . . ?
C15 C12 C5 O1 -42.0(4) . . . . ?
C3 C12 C5 C16 15.3(4) . . . . ?
C15 C12 C5 C16 139.1(3) . . . . ?
C21 C10 C3 C12 6.4(3) . . . . ?
C5 C12 C3 C10 150.3(3) . . . . ?
C15 C12 C3 C10 21.3(3) . . . . ?
C13 C7 C1 C20 15.2(4) . . . . ?
C21 C20 C1 C7 -167.4(2) . . . . ?
C8 C20 C1 C7 -45.3(3) . . . . ?
O3 C28 C24 C23 178.4(2) . . . . ?
C22 C28 C24 C23 58.1(3) . . . . ?
C28 C24 C23 C19 -56.4(3) . . . . ?
C13 C19 C23 C24 49.9(3) . . . . ?
C14 C19 C23 C24 -68.4(3) . . . . ?
C8 C19 C23 C24 169.1(2) . . . . ?
O3 C28 C22 C13 -174.8(3) . . . . ?
C24 C28 C22 C13 -56.6(3) . . . . ?
C7 C13 C22 C28 -126.6(3) . . . . ?
C19 C13 C22 C28 53.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.049
