# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_test_a
_database_code_depnum_ccdc_archive 'CCDC 1991530'
loop_
_audit_author_name
_audit_author_address
'Davi Fernando Back'
;Federal University of Santa Maria
Brazil
;
_audit_update_record             
;
2020-03-19 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;

_audit_creation_date             2019-06-14T16:48:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
'1-methyl-4-phenyl-3-((3-(trifluoromethyl)phenyl)selanyl)-1-azaspiro        [4.5]deca-3,6,9-triene-2,8-dione'
_chemical_name_common            'phenylselanyl azaspiro decatrienedione'
_chemical_formula_moiety         'C23 H16 F3 N O2 Se'
_chemical_formula_sum            'C23 H16 F3 N O2 Se'
_chemical_formula_weight         474.33
_chemical_melting_point          421K
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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                   5.7568(4)
_cell_length_b                   25.3971(13)
_cell_length_c                   13.5914(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.147(2)
_cell_angle_gamma                90
_cell_volume                     1967.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7325
_cell_measurement_theta_min      2.843
_cell_measurement_theta_max      26.774

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       tabular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.6504
_exptl_absorpt_correction_T_max  0.9358

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_number            22029
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         27.16
_diffrn_reflns_theta_full        27.16
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             4358
_reflns_number_gt                3415
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0441P)²+1.6050P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         4358
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.041
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.064

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
N N 0.0061 0.0033 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Se11 Se 0.40415(5) 0.568508(12) 0.39990(2) 0.03602(11) Uani 1 1 d . . .
O13 O 0.2095(4) 0.69088(9) 0.38162(15) 0.0478(6) Uani 1 1 d . . .
N7 N 0.3626(4) 0.70788(9) 0.54354(16) 0.0312(5) Uani 1 1 d . . .
F1 F 0.1853(4) 0.61347(10) -0.02172(16) 0.0787(7) Uani 1 1 d . . .
F3 F 0.2396(6) 0.53255(10) 0.01120(16) 0.1014(10) Uani 1 1 d . . .
F2 F 0.4783(6) 0.57481(12) -0.06409(16) 0.0980(9) Uani 1 1 d . . .
O27 O 0.7185(5) 0.72333(14) 0.91881(17) 0.0750(9) Uani 1 1 d . . .
C10 C 0.5679(4) 0.62917(10) 0.57714(17) 0.0249(5) Uani 1 1 d . . .
C12 C 0.7376(5) 0.59120(10) 0.62858(18) 0.0263(6) Uani 1 1 d . . .
C9 C 0.4524(5) 0.62776(10) 0.48488(18) 0.0278(6) Uani 1 1 d . . .
C8 C 0.3248(5) 0.67817(11) 0.46002(19) 0.0308(6) Uani 1 1 d . . .
C5 C 0.5104(4) 0.68150(10) 0.62593(18) 0.0249(5) Uani 1 1 d . . .
C6 C 0.3638(5) 0.67218(11) 0.70756(19) 0.0287(6) Uani 1 1 d . . .
H6 H 0.2234 0.6539 0.6921 0.034 Uiso 1 1 calc R . .
C3 C 0.7931(5) 0.72689(12) 0.7534(2) 0.0346(6) Uani 1 1 d . . .
H3 H 0.9323 0.7455 0.77 0.042 Uiso 1 1 calc R . .
C4 C 0.7274(5) 0.71250(11) 0.6595(2) 0.0298(6) Uani 1 1 d . . .
H4 H 0.8215 0.7223 0.6123 0.036 Uiso 1 1 calc R . .
C20 C 0.3982(5) 0.57990(11) 0.1926(2) 0.0343(6) Uani 1 1 d . . .
H20 H 0.2574 0.5616 0.1895 0.041 Uiso 1 1 calc R . .
C21 C 0.9140(5) 0.57081(11) 0.5787(2) 0.0355(6) Uani 1 1 d . . .
H21 H 0.9168 0.5797 0.5125 0.043 Uiso 1 1 calc R . .
C15 C 0.5205(5) 0.59468(11) 0.28367(19) 0.0314(6) Uani 1 1 d . . .
C14 C 0.2784(5) 0.76096(11) 0.5524(2) 0.0382(7) Uani 1 1 d . . .
H14A H 0.3278 0.7736 0.6186 0.057 Uiso 1 1 calc R . .
H14B H 0.1102 0.7613 0.5389 0.057 Uiso 1 1 calc R . .
H14C H 0.3413 0.7833 0.5056 0.057 Uiso 1 1 calc R . .
C16 C 0.7253(5) 0.62298(12) 0.2881(2) 0.0400(7) Uani 1 1 d . . .
H16 H 0.8054 0.6333 0.3493 0.048 Uiso 1 1 calc R . .
C25 C 0.7378(6) 0.57702(11) 0.7275(2) 0.0384(7) Uani 1 1 d . . .
H25 H 0.6212 0.5898 0.7621 0.046 Uiso 1 1 calc R . .
C1 C 0.4237(5) 0.68853(12) 0.8002(2) 0.0360(7) Uani 1 1 d . . .
H1 H 0.32 0.6838 0.846 0.043 Uiso 1 1 calc R . .
C22 C 1.0838(5) 0.53772(12) 0.6263(3) 0.0434(7) Uani 1 1 d . . .
H22 H 1.1994 0.5242 0.5921 0.052 Uiso 1 1 calc R . .
C19 C 0.4877(6) 0.59259(12) 0.1066(2) 0.0395(7) Uani 1 1 d . . .
C23 C 1.0825(6) 0.52458(12) 0.7247(2) 0.0453(8) Uani 1 1 d . . .
H23 H 1.198 0.5026 0.757 0.054 Uiso 1 1 calc R . .
C2 C 0.6493(5) 0.71390(13) 0.8316(2) 0.0406(7) Uani 1 1 d . . .
C17 C 0.8120(6) 0.63599(13) 0.2016(3) 0.0477(8) Uani 1 1 d . . .
H17 H 0.9502 0.6553 0.2048 0.057 Uiso 1 1 calc R . .
C18 C 0.6948(6) 0.62060(13) 0.1105(2) 0.0475(8) Uani 1 1 d . . .
H18 H 0.7545 0.629 0.0524 0.057 Uiso 1 1 calc R . .
C24 C 0.9092(6) 0.54422(13) 0.7748(2) 0.0452(8) Uani 1 1 d . . .
H24 H 0.908 0.5353 0.8411 0.054 Uiso 1 1 calc R . .
C26 C 0.3506(7) 0.57760(14) 0.0090(2) 0.0548(9) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Se11 C9 1.893(3) . ?
Se11 C15 1.920(3) . ?
O13 C8 1.217(3) . ?
N7 C8 1.355(3) . ?
N7 C14 1.443(4) . ?
N7 C5 1.469(3) . ?
F1 C26 1.341(4) . ?
F3 C26 1.313(4) . ?
F2 C26 1.319(4) . ?
O27 C2 1.219(3) . ?
C10 C9 1.334(3) . ?
C10 C12 1.477(4) . ?
C10 C5 1.542(4) . ?
C12 C25 1.392(4) . ?
C12 C21 1.398(4) . ?
C9 C8 1.491(4) . ?
C5 C4 1.492(4) . ?
C5 C6 1.505(4) . ?
C6 C1 1.324(4) . ?
C3 C4 1.329(4) . ?
C3 C2 1.475(4) . ?
C20 C19 1.381(4) . ?
C20 C15 1.386(4) . ?
C21 C22 1.379(4) . ?
C15 C16 1.375(4) . ?
C16 C17 1.381(4) . ?
C25 C24 1.379(4) . ?
C1 C2 1.459(4) . ?
C22 C23 1.379(5) . ?
C19 C18 1.382(5) . ?
C19 C26 1.493(4) . ?
C23 C24 1.379(5) . ?
C17 C18 1.380(5) . ?

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 Se11 C15 100.87(11) . . ?
C8 N7 C14 125.0(2) . . ?
C8 N7 C5 113.1(2) . . ?
C14 N7 C5 121.8(2) . . ?
C9 C10 C12 129.5(2) . . ?
C9 C10 C5 108.6(2) . . ?
C12 C10 C5 121.8(2) . . ?
C25 C12 C21 118.2(3) . . ?
C25 C12 C10 122.4(2) . . ?
C21 C12 C10 119.3(2) . . ?
C10 C9 C8 110.7(2) . . ?
C10 C9 Se11 127.3(2) . . ?
C8 C9 Se11 121.29(18) . . ?
O13 C8 N7 126.1(3) . . ?
O13 C8 C9 128.1(3) . . ?
N7 C8 C9 105.8(2) . . ?
N7 C5 C4 111.2(2) . . ?
N7 C5 C6 108.0(2) . . ?
C4 C5 C6 113.0(2) . . ?
N7 C5 C10 101.63(19) . . ?
C4 C5 C10 111.4(2) . . ?
C6 C5 C10 111.0(2) . . ?
C1 C6 C5 123.7(2) . . ?
C4 C3 C2 121.2(3) . . ?
C3 C4 C5 123.4(3) . . ?
C19 C20 C15 119.3(3) . . ?
C22 C21 C12 120.9(3) . . ?
C16 C15 C20 120.3(3) . . ?
C16 C15 Se11 122.8(2) . . ?
C20 C15 Se11 116.7(2) . . ?
C15 C16 C17 119.9(3) . . ?
C24 C25 C12 120.6(3) . . ?
C6 C1 C2 121.2(3) . . ?
C23 C22 C21 120.1(3) . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 C26 118.6(3) . . ?
C18 C19 C26 120.7(3) . . ?
C22 C23 C24 119.7(3) . . ?
O27 C2 C1 121.7(3) . . ?
O27 C2 C3 121.2(3) . . ?
C1 C2 C3 117.1(2) . . ?
C18 C17 C16 120.4(3) . . ?
C17 C18 C19 119.4(3) . . ?
C25 C24 C23 120.6(3) . . ?
F3 C26 F2 107.2(3) . . ?
F3 C26 F1 105.8(3) . . ?
F2 C26 F1 104.4(3) . . ?
F3 C26 C19 113.6(3) . . ?
F2 C26 C19 113.7(3) . . ?
F1 C26 C19 111.5(3) . . ?

# END of CIF
####################################################################### 
# 
# 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_teste2_a
_database_code_depnum_ccdc_archive 'CCDC 1991531'
loop_
_audit_author_name
_audit_author_address
'Davi Fernando Back' 'Federal University of Santa Maria'
_audit_update_record             
;
2020-03-19 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;

_audit_creation_date             2019-06-14T17:16:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
1-methyl-4-phenyl-3-(phenylselanyl)-1-azaspiro[4.5]deca-3,7,9-triene-2,6-dione
;
_chemical_name_common            'azaspiro deca trienedione'
_chemical_formula_moiety         'C44 H34 N2 O4 Se2'
_chemical_formula_sum            'C44 H34 N2 O4 Se2'
_chemical_formula_weight         812.65
_chemical_melting_point          none
_chemical_absolute_configuration rmad
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P1c1
_symmetry_space_group_name_Hall  P-2yc


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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

_cell_length_a                   9.6477(5)
_cell_length_b                   14.9116(8)
_cell_length_c                   13.3181(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.129(2)
_cell_angle_gamma                90
_cell_volume                     1896.73(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9259
_cell_measurement_theta_min      2.532
_cell_measurement_theta_max      25.547

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.5201
_exptl_absorpt_correction_T_max  0.6811

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_number            78808
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         28.4
_diffrn_reflns_theta_full        28.4
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             9479
_reflns_number_gt                7599
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond (version 3.2i); Crystal Impact GbR'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0699P)²+0.0316P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         9479
_refine_ls_number_parameters     469
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.021(7)
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.18

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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
Se37 Se 0.60344(3) 0.25062(2) 0.29067(3) 0.06019(10) Uani 1 1 d . . .
Se11 Se 0.09038(4) 0.26893(3) 0.76587(3) 0.08211(16) Uani 1 1 d . . .
O39 O 0.5804(2) 0.46518(16) 0.36095(17) 0.0632(5) Uani 1 1 d . . .
O52 O 0.9089(3) 0.4933(2) 0.1839(2) 0.0899(8) Uani 1 1 d . . .
O26 O 0.4130(3) 0.0008(2) 0.7514(2) 0.0855(8) Uani 1 1 d . . .
N33 N 0.8184(2) 0.48140(17) 0.37314(19) 0.0553(6) Uani 1 1 d . . .
O13 O 0.1208(3) 0.1010(2) 0.9348(2) 0.0975(10) Uani 1 1 d . . .
C4 C 0.5010(3) 0.0513(2) 0.7919(2) 0.0609(8) Uani 1 1 d . . .
C10 C 0.3664(3) 0.1929(2) 0.79757(18) 0.0483(6) Uani 1 1 d . . .
C42 C 0.5411(3) 0.3667(2) 0.1155(2) 0.0581(7) Uani 1 1 d . . .
H42 H 0.6305 0.3904 0.1329 0.07 Uiso 1 1 calc R . .
C35 C 0.7345(3) 0.34521(19) 0.3205(2) 0.0474(6) Uani 1 1 d . . .
N7 N 0.3555(3) 0.0891(2) 0.92431(18) 0.0675(7) Uani 1 1 d . . .
C34 C 0.6976(3) 0.4356(2) 0.35230(19) 0.0495(6) Uani 1 1 d . . .
C31 C 0.9377(3) 0.4299(2) 0.3512(2) 0.0530(6) Uani 1 1 d . . .
C41 C 0.4927(3) 0.3014(2) 0.1741(2) 0.0496(6) Uani 1 1 d . . .
C5 C 0.4562(3) 0.1244(2) 0.86366(19) 0.0526(6) Uani 1 1 d . . .
C9 C 0.2364(3) 0.1897(2) 0.8187(2) 0.0576(7) Uani 1 1 d . . .
C15 C -0.0141(3) 0.1947(2) 0.6661(2) 0.0590(7) Uani 1 1 d . . .
C36 C 0.8718(3) 0.33850(19) 0.3214(2) 0.0485(6) Uani 1 1 d . . .
C6 C 0.5769(4) 0.1713(3) 0.9277(2) 0.0738(10) Uani 1 1 d . . .
H6 H 0.5594 0.2089 0.9802 0.089 Uiso 1 1 calc R . .
C32 C 1.0466(3) 0.4217(3) 0.4439(3) 0.0731(9) Uani 1 1 d . . .
H32 H 1.0181 0.4128 0.507 0.088 Uiso 1 1 calc R . .
C3 C 0.6457(4) 0.0477(4) 0.7779(3) 0.0867(12) Uani 1 1 d . . .
H3 H 0.6735 0.0095 0.7292 0.104 Uiso 1 1 calc R . .
C16 C 0.0326(4) 0.1145(3) 0.6341(3) 0.0744(9) Uani 1 1 d . . .
H16 H 0.1192 0.0924 0.6631 0.089 Uiso 1 1 calc R . .
C30 C 0.9920(4) 0.4655(3) 0.2551(3) 0.0655(8) Uani 1 1 d . . .
C43 C 0.4541(4) 0.3973(2) 0.0294(2) 0.0723(9) Uani 1 1 d . . .
H43 H 0.4861 0.4414 -0.0111 0.087 Uiso 1 1 calc R . .
C12 C 0.4208(4) 0.2478(2) 0.7196(2) 0.0525(7) Uani 1 1 d . . .
C21 C 0.4978(4) 0.3238(2) 0.7445(3) 0.0680(8) Uani 1 1 d . . .
H21 H 0.5193 0.341 0.812 0.082 Uiso 1 1 calc R . .
C17 C -0.0480(5) 0.0664(3) 0.5590(3) 0.0894(12) Uani 1 1 d . . .
H17 H -0.0152 0.0126 0.5361 0.107 Uiso 1 1 calc R . .
C40 C 0.8298(4) 0.5737(2) 0.4060(3) 0.0724(9) Uani 1 1 d . . .
H40A H 0.9264 0.5914 0.4153 0.109 Uiso 1 1 calc R . .
H40B H 0.793 0.5798 0.4689 0.109 Uiso 1 1 calc R . .
H40C H 0.7776 0.6111 0.3555 0.109 Uiso 1 1 calc R . .
C22 C 0.5437(5) 0.3752(3) 0.6687(4) 0.0866(11) Uani 1 1 d . . .
H22 H 0.5947 0.4273 0.6854 0.104 Uiso 1 1 calc R . .
C8 C 0.2247(4) 0.1217(3) 0.8981(2) 0.0687(9) Uani 1 1 d . . .
C1 C 0.7068(4) 0.1595(3) 0.9099(4) 0.0948(15) Uani 1 1 d . . .
H1 H 0.7782 0.1918 0.9478 0.114 Uiso 1 1 calc R . .
C38 C 0.9538(3) 0.2614(2) 0.2915(3) 0.0568(7) Uani 1 1 d . . .
C27 C 1.1783(4) 0.4269(3) 0.4373(4) 0.0926(14) Uani 1 1 d . . .
H27 H 1.2424 0.42 0.4959 0.111 Uiso 1 1 calc R . .
C23 C 0.5139(5) 0.3492(3) 0.5694(3) 0.0880(13) Uani 1 1 d . . .
H23 H 0.5476 0.3825 0.519 0.106 Uiso 1 1 calc R . .
C46 C 0.3580(4) 0.2675(3) 0.1489(3) 0.0679(9) Uani 1 1 d . . .
H46 H 0.3237 0.2247 0.1899 0.081 Uiso 1 1 calc R . .
C2 C 0.7416(4) 0.0989(4) 0.8346(4) 0.0959(14) Uani 1 1 d . . .
H2 H 0.8346 0.0945 0.8241 0.115 Uiso 1 1 calc R . .
C20 C -0.1427(5) 0.2276(3) 0.6240(3) 0.0813(11) Uani 1 1 d . . .
H20 H -0.1752 0.282 0.6457 0.098 Uiso 1 1 calc R . .
C44 C 0.3237(5) 0.3631(3) 0.0045(3) 0.0775(11) Uani 1 1 d . . .
H44 H 0.2665 0.3842 -0.0528 0.093 Uiso 1 1 calc R . .
C18 C -0.1775(5) 0.0986(4) 0.5182(4) 0.0981(14) Uani 1 1 d . . .
H18 H -0.234 0.0655 0.4693 0.118 Uiso 1 1 calc R . .
C45 C 0.2756(4) 0.2982(3) 0.0625(3) 0.0809(11) Uani 1 1 d . . .
H45 H 0.1866 0.2743 0.0439 0.097 Uiso 1 1 calc R . .
C29 C 1.1433(4) 0.4595(3) 0.2557(5) 0.0925(14) Uani 1 1 d . . .
H29 H 1.1814 0.4673 0.196 0.111 Uiso 1 1 calc R . .
C28 C 1.2286(4) 0.4424(3) 0.3448(6) 0.1080(19) Uani 1 1 d . . .
H28 H 1.3248 0.4411 0.3441 0.13 Uiso 1 1 calc R . .
C19 C -0.2224(5) 0.1785(4) 0.5491(3) 0.1015(16) Uani 1 1 d . . .
H19 H -0.3087 0.2007 0.5195 0.122 Uiso 1 1 calc R . .
C25 C 0.3881(4) 0.2227(3) 0.6186(3) 0.0686(8) Uani 1 1 d . . .
H25 H 0.3352 0.1715 0.6012 0.082 Uiso 1 1 calc R . .
C14 C 0.3915(5) 0.0199(4) 0.9995(3) 0.1053(16) Uani 1 1 d . . .
H14A H 0.49 0.0076 1.0056 0.158 Uiso 1 1 calc R . .
H14B H 0.3397 -0.0336 0.9792 0.158 Uiso 1 1 calc R . .
H14C H 0.3687 0.0399 1.0637 0.158 Uiso 1 1 calc R . .
C47 C 0.9378(5) 0.2370(3) 0.1908(4) 0.0785(11) Uani 1 1 d . . .
H47 H 0.8781 0.2696 0.1433 0.094 Uiso 1 1 calc R . .
C49 C 1.0989(5) 0.1167(3) 0.2319(6) 0.114(2) Uani 1 1 d . . .
H49 H 1.1476 0.0672 0.2126 0.136 Uiso 1 1 calc R . .
C51 C 1.0427(4) 0.2143(3) 0.3603(4) 0.0823(11) Uani 1 1 d . . .
H51 H 1.0553 0.2309 0.4283 0.099 Uiso 1 1 calc R . .
C48 C 1.0104(5) 0.1643(4) 0.1603(5) 0.1062(16) Uani 1 1 d . . .
H48 H 0.9998 0.1476 0.0923 0.127 Uiso 1 1 calc R . .
C24 C 0.4353(5) 0.2749(3) 0.5441(3) 0.0810(11) Uani 1 1 d . . .
H24 H 0.4129 0.2588 0.4763 0.097 Uiso 1 1 calc R . .
C50 C 1.1138(5) 0.1422(3) 0.3289(5) 0.1056(16) Uani 1 1 d . . .
H50 H 1.1741 0.1102 0.3766 0.127 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Se37 C35 1.898(3) . ?
Se37 C41 1.912(3) . ?
Se11 C9 1.896(3) . ?
Se11 C15 1.905(3) . ?
O39 C34 1.234(3) . ?
O52 C30 1.224(5) . ?
O26 C4 1.204(4) . ?
N33 C34 1.346(4) . ?
N33 C40 1.443(4) . ?
N33 C31 1.447(4) . ?
O13 C8 1.215(4) . ?
C4 C3 1.435(5) . ?
C4 C5 1.551(5) . ?
C10 C9 1.325(4) . ?
C10 C12 1.476(4) . ?
C10 C5 1.534(4) . ?
C42 C41 1.371(4) . ?
C42 C43 1.399(5) . ?
C35 C36 1.327(4) . ?
C35 C34 1.472(4) . ?
N7 C8 1.351(5) . ?
N7 C14 1.445(5) . ?
N7 C5 1.448(4) . ?
C31 C32 1.509(4) . ?
C31 C36 1.532(4) . ?
C31 C30 1.545(5) . ?
C41 C46 1.390(4) . ?
C5 C6 1.514(4) . ?
C9 C8 1.482(5) . ?
C15 C16 1.367(5) . ?
C15 C20 1.377(5) . ?
C36 C38 1.481(4) . ?
C6 C1 1.320(6) . ?
C32 C27 1.288(5) . ?
C3 C2 1.346(7) . ?
C16 C17 1.378(6) . ?
C30 C29 1.461(5) . ?
C43 C44 1.355(6) . ?
C12 C21 1.370(5) . ?
C12 C25 1.388(5) . ?
C21 C22 1.389(5) . ?
C17 C18 1.377(6) . ?
C22 C23 1.369(7) . ?
C1 C2 1.425(8) . ?
C38 C51 1.358(5) . ?
C38 C47 1.377(6) . ?
C27 C28 1.406(8) . ?
C23 C24 1.358(7) . ?
C46 C45 1.381(6) . ?
C20 C19 1.381(7) . ?
C44 C45 1.361(6) . ?
C18 C19 1.351(7) . ?
C29 C28 1.369(9) . ?
C25 C24 1.387(6) . ?
C47 C48 1.383(6) . ?
C49 C50 1.336(9) . ?
C49 C48 1.383(9) . ?
C51 C50 1.373(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C35 Se37 C41 98.91(12) . . ?
C9 Se11 C15 100.90(13) . . ?
C34 N33 C40 124.9(3) . . ?
C34 N33 C31 112.3(2) . . ?
C40 N33 C31 122.6(2) . . ?
O26 C4 C3 123.7(4) . . ?
O26 C4 C5 118.4(3) . . ?
C3 C4 C5 117.9(3) . . ?
C9 C10 C12 127.7(3) . . ?
C9 C10 C5 109.2(3) . . ?
C12 C10 C5 123.0(2) . . ?
C41 C42 C43 119.0(3) . . ?
C36 C35 C34 110.4(2) . . ?
C36 C35 Se37 125.5(2) . . ?
C34 C35 Se37 124.07(19) . . ?
C8 N7 C14 124.0(3) . . ?
C8 N7 C5 113.7(3) . . ?
C14 N7 C5 122.1(3) . . ?
O39 C34 N33 125.3(3) . . ?
O39 C34 C35 128.0(3) . . ?
N33 C34 C35 106.7(2) . . ?
N33 C31 C32 111.1(3) . . ?
N33 C31 C36 102.3(2) . . ?
C32 C31 C36 110.8(3) . . ?
N33 C31 C30 110.9(3) . . ?
C32 C31 C30 115.3(3) . . ?
C36 C31 C30 105.5(2) . . ?
C42 C41 C46 120.2(3) . . ?
C42 C41 Se37 123.2(2) . . ?
C46 C41 Se37 116.6(2) . . ?
N7 C5 C6 112.2(2) . . ?
N7 C5 C10 101.2(2) . . ?
C6 C5 C10 110.0(3) . . ?
N7 C5 C4 110.8(3) . . ?
C6 C5 C4 114.4(3) . . ?
C10 C5 C4 107.4(2) . . ?
C10 C9 C8 110.3(3) . . ?
C10 C9 Se11 125.1(2) . . ?
C8 C9 Se11 124.3(2) . . ?
C16 C15 C20 120.1(4) . . ?
C16 C15 Se11 124.1(2) . . ?
C20 C15 Se11 115.7(3) . . ?
C35 C36 C38 128.8(3) . . ?
C35 C36 C31 108.2(2) . . ?
C38 C36 C31 122.8(2) . . ?
C1 C6 C5 120.7(4) . . ?
C27 C32 C31 121.3(4) . . ?
C2 C3 C4 120.7(5) . . ?
C15 C16 C17 120.3(3) . . ?
O52 C30 C29 124.7(4) . . ?
O52 C30 C31 119.8(3) . . ?
C29 C30 C31 115.4(4) . . ?
C44 C43 C42 120.5(3) . . ?
C21 C12 C25 119.9(3) . . ?
C21 C12 C10 121.5(3) . . ?
C25 C12 C10 118.5(3) . . ?
C12 C21 C22 119.9(4) . . ?
C18 C17 C16 119.5(4) . . ?
C23 C22 C21 120.1(4) . . ?
O13 C8 N7 126.8(4) . . ?
O13 C8 C9 127.7(4) . . ?
N7 C8 C9 105.5(3) . . ?
C6 C1 C2 122.4(4) . . ?
C51 C38 C47 119.5(3) . . ?
C51 C38 C36 122.0(4) . . ?
C47 C38 C36 118.4(3) . . ?
C32 C27 C28 122.4(4) . . ?
C24 C23 C22 120.3(3) . . ?
C45 C46 C41 119.3(3) . . ?
C3 C2 C1 122.9(4) . . ?
C15 C20 C19 118.9(4) . . ?
C43 C44 C45 120.5(3) . . ?
C19 C18 C17 119.9(4) . . ?
C44 C45 C46 120.4(3) . . ?
C28 C29 C30 119.6(4) . . ?
C29 C28 C27 123.4(3) . . ?
C18 C19 C20 121.2(4) . . ?
C12 C25 C24 119.3(4) . . ?
C38 C47 C48 120.1(5) . . ?
C50 C49 C48 119.5(4) . . ?
C38 C51 C50 119.7(5) . . ?
C47 C48 C49 119.3(5) . . ?
C23 C24 C25 120.6(4) . . ?
C49 C50 C51 121.9(5) . . ?

# END of CIF
