# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1522109'
_audit_update_record             
;
2016-12-10 deposited with the CCDC.
2017-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 F N0 O2 S Se'
_chemical_formula_weight         431.37

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   7.1841(14)
_cell_length_b                   18.013(4)
_cell_length_c                   14.832(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.33(3)
_cell_angle_gamma                90.00
_cell_volume                     1911.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4234
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.97

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    2.095
_exptl_absorpt_correction_type   none
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15560
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         27.22
_reflns_number_total             4214
_reflns_number_gt                3050
_reflns_threshold_expression     I>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-97 (Sheldrick, 2008)'
_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)+(0.1164P)²+1.3154P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4214
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1890
_refine_ls_wR_factor_gt          0.1703
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.22666(7) 1.03088(3) 0.58920(3) 0.0486(2) Uani 1 1 d . . .
S2 S 0.41233(15) 0.86193(6) 0.80615(8) 0.0467(3) Uani 1 1 d . . .
C7 C 0.2484(6) 0.9449(2) 0.6644(3) 0.0392(9) Uani 1 1 d . . .
C9 C 0.4242(6) 1.0910(2) 0.6457(3) 0.0406(9) Uani 1 1 d . . .
O1 O 0.3426(5) 0.79658(18) 0.7601(2) 0.0581(9) Uani 1 1 d . . .
C6 C 0.1069(6) 0.8889(2) 0.6289(3) 0.0400(9) Uani 1 1 d . . .
O2 O 0.6062(5) 0.8648(2) 0.8390(3) 0.0677(10) Uani 1 1 d . . .
C8 C 0.3737(6) 0.9392(2) 0.7360(3) 0.0443(10) Uani 1 1 d . . .
H8A H 0.4482 0.9806 0.7500 0.053 Uiso 1 1 calc R . .
C4 C -0.2119(7) 0.8476(3) 0.6061(4) 0.0645(15) Uani 1 1 d . . .
H4A H -0.3354 0.8514 0.6197 0.077 Uiso 1 1 calc R . .
C1 C 0.1487(6) 0.8346(3) 0.5682(3) 0.0490(11) Uani 1 1 d . . .
C14 C 0.3816(7) 1.1463(3) 0.7051(4) 0.0555(12) Uani 1 1 d . . .
H14A H 0.2591 1.1536 0.7187 0.067 Uiso 1 1 calc R . .
C10 C 0.6057(7) 1.0812(3) 0.6260(3) 0.0566(12) Uani 1 1 d . . .
H10A H 0.6351 1.0440 0.5863 0.068 Uiso 1 1 calc R . .
C2 C 0.0171(8) 0.7891(3) 0.5260(4) 0.0624(14) Uani 1 1 d . . .
H2A H 0.0497 0.7539 0.4843 0.075 Uiso 1 1 calc R . .
C5 C -0.0756(6) 0.8956(3) 0.6483(3) 0.0504(11) Uani 1 1 d . . .
H5A H -0.1088 0.9315 0.6889 0.060 Uiso 1 1 calc R . .
C18 C 0.0713(9) 0.9070(4) 1.0439(4) 0.0709(16) Uani 1 1 d . . .
C20 C 0.0933(7) 0.8588(3) 0.8927(3) 0.0592(13) Uani 1 1 d . . .
H20A H 0.0376 0.8358 0.8410 0.071 Uiso 1 1 calc R . .
C3 C -0.1650(8) 0.7961(3) 0.5461(4) 0.0643(15) Uani 1 1 d . . .
H3A H -0.2566 0.7651 0.5181 0.077 Uiso 1 1 calc R . .
C12 C 0.7025(8) 1.1817(3) 0.7243(4) 0.0671(15) Uani 1 1 d . . .
H12A H 0.7966 1.2124 0.7506 0.081 Uiso 1 1 calc R . .
C15 C 0.2782(6) 0.8783(3) 0.8979(3) 0.0492(11) Uani 1 1 d . . .
C16 C 0.3630(8) 0.9112(3) 0.9767(3) 0.0585(13) Uani 1 1 d . . .
H16A H 0.4891 0.9238 0.9812 0.070 Uiso 1 1 calc R . .
C13 C 0.5240(8) 1.1904(3) 0.7437(4) 0.0637(14) Uani 1 1 d . . .
H13A H 0.4964 1.2273 0.7842 0.076 Uiso 1 1 calc R . .
C11 C 0.7427(8) 1.1265(4) 0.6651(4) 0.0731(17) Uani 1 1 d . . .
H11A H 0.8654 1.1199 0.6515 0.088 Uiso 1 1 calc R . .
C17 C 0.2570(9) 0.9246(4) 1.0475(4) 0.0717(16) Uani 1 1 d . . .
H17A H 0.3137 0.9464 1.0998 0.086 Uiso 1 1 calc R . .
C19 C -0.0095(8) 0.8735(4) 0.9643(4) 0.0716(16) Uani 1 1 d . . .
H19A H -0.1356 0.8609 0.9599 0.086 Uiso 1 1 calc R . .
F1 F 0.3291(6) 0.8260(3) 0.5530(3) 0.1073(14) Uani 1 1 d . . .
C21 C -0.0446(12) 0.9231(5) 1.1207(5) 0.102(3) Uani 1 1 d . . .
H21A H 0.0324 0.9456 1.1696 0.153 Uiso 1 1 calc R . .
H21B H -0.0961 0.8776 1.1413 0.153 Uiso 1 1 calc R . .
H21C H -0.1443 0.9563 1.1004 0.153 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 C7 1.906(4) . ?
Se1 C9 1.915(4) . ?
S2 O1 1.428(4) . ?
S2 O2 1.433(3) . ?
S2 C8 1.745(4) . ?
S2 C15 1.764(5) . ?
C7 C8 1.330(6) . ?
C7 C6 1.494(6) . ?
C9 C10 1.374(6) . ?
C9 C14 1.383(6) . ?
C6 C5 1.373(6) . ?
C6 C1 1.381(6) . ?
C8 H8A 0.9300 . ?
C4 C3 1.350(8) . ?
C4 C5 1.409(7) . ?
C4 H4A 0.9300 . ?
C1 F1 1.345(6) . ?
C1 C2 1.359(7) . ?
C14 C13 1.378(7) . ?
C14 H14A 0.9300 . ?
C10 C11 1.366(8) . ?
C10 H10A 0.9300 . ?
C2 C3 1.374(8) . ?
C2 H2A 0.9300 . ?
C5 H5A 0.9300 . ?
C18 C17 1.368(9) . ?
C18 C19 1.403(9) . ?
C18 C21 1.500(9) . ?
C20 C15 1.369(7) . ?
C20 C19 1.374(8) . ?
C20 H20A 0.9300 . ?
C3 H3A 0.9300 . ?
C12 C13 1.349(8) . ?
C12 C11 1.374(9) . ?
C12 H12A 0.9300 . ?
C15 C16 1.399(7) . ?
C16 C17 1.374(8) . ?
C16 H16A 0.9300 . ?
C13 H13A 0.9300 . ?
C11 H11A 0.9300 . ?
C17 H17A 0.9300 . ?
C19 H19A 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C7 Se1 C9 100.69(17) . . ?
O1 S2 O2 118.6(2) . . ?
O1 S2 C8 110.0(2) . . ?
O2 S2 C8 105.7(2) . . ?
O1 S2 C15 108.3(2) . . ?
O2 S2 C15 108.4(2) . . ?
C8 S2 C15 105.0(2) . . ?
C8 C7 C6 128.1(4) . . ?
C8 C7 Se1 122.9(3) . . ?
C6 C7 Se1 109.0(3) . . ?
C10 C9 C14 119.9(4) . . ?
C10 C9 Se1 120.9(3) . . ?
C14 C9 Se1 119.1(4) . . ?
C5 C6 C1 117.9(4) . . ?
C5 C6 C7 119.9(4) . . ?
C1 C6 C7 121.8(4) . . ?
C7 C8 S2 126.6(4) . . ?
C7 C8 H8A 116.7 . . ?
S2 C8 H8A 116.7 . . ?
C3 C4 C5 120.6(5) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
F1 C1 C2 119.5(5) . . ?
F1 C1 C6 117.5(4) . . ?
C2 C1 C6 122.9(5) . . ?
C13 C14 C9 118.7(5) . . ?
C13 C14 H14A 120.7 . . ?
C9 C14 H14A 120.7 . . ?
C11 C10 C9 119.6(5) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
C1 C2 C3 118.7(5) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 H2A 120.6 . . ?
C6 C5 C4 119.4(5) . . ?
C6 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
C17 C18 C19 117.2(5) . . ?
C17 C18 C21 122.3(6) . . ?
C19 C18 C21 120.4(6) . . ?
C15 C20 C19 119.8(5) . . ?
C15 C20 H20A 120.1 . . ?
C19 C20 H20A 120.1 . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C13 C12 C11 118.7(5) . . ?
C13 C12 H12A 120.6 . . ?
C11 C12 H12A 120.6 . . ?
C20 C15 C16 120.0(5) . . ?
C20 C15 S2 120.7(4) . . ?
C16 C15 S2 119.2(4) . . ?
C17 C16 C15 118.9(5) . . ?
C17 C16 H16A 120.6 . . ?
C15 C16 H16A 120.6 . . ?
C12 C13 C14 121.9(5) . . ?
C12 C13 H13A 119.1 . . ?
C14 C13 H13A 119.1 . . ?
C10 C11 C12 121.2(5) . . ?
C10 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
C18 C17 C16 122.6(5) . . ?
C18 C17 H17A 118.7 . . ?
C16 C17 H17A 118.7 . . ?
C20 C19 C18 121.5(6) . . ?
C20 C19 H19A 119.2 . . ?
C18 C19 H19A 119.2 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C9 Se1 C7 C8 1.5(4) . . . . ?
C9 Se1 C7 C6 -178.1(3) . . . . ?
C7 Se1 C9 C10 83.0(4) . . . . ?
C7 Se1 C9 C14 -98.9(4) . . . . ?
C8 C7 C6 C5 100.2(6) . . . . ?
Se1 C7 C6 C5 -80.2(4) . . . . ?
C8 C7 C6 C1 -87.3(6) . . . . ?
Se1 C7 C6 C1 92.3(4) . . . . ?
C6 C7 C8 S2 2.6(7) . . . . ?
Se1 C7 C8 S2 -177.0(3) . . . . ?
O1 S2 C8 C7 21.2(5) . . . . ?
O2 S2 C8 C7 150.3(4) . . . . ?
C15 S2 C8 C7 -95.2(5) . . . . ?
C5 C6 C1 F1 -176.8(4) . . . . ?
C7 C6 C1 F1 10.5(7) . . . . ?
C5 C6 C1 C2 1.4(7) . . . . ?
C7 C6 C1 C2 -171.3(5) . . . . ?
C10 C9 C14 C13 -0.3(7) . . . . ?
Se1 C9 C14 C13 -178.4(4) . . . . ?
C14 C9 C10 C11 -0.2(8) . . . . ?
Se1 C9 C10 C11 177.8(4) . . . . ?
F1 C1 C2 C3 176.5(5) . . . . ?
C6 C1 C2 C3 -1.6(8) . . . . ?
C1 C6 C5 C4 0.0(7) . . . . ?
C7 C6 C5 C4 172.7(4) . . . . ?
C3 C4 C5 C6 -1.0(7) . . . . ?
C5 C4 C3 C2 0.8(8) . . . . ?
C1 C2 C3 C4 0.5(8) . . . . ?
C19 C20 C15 C16 1.7(8) . . . . ?
C19 C20 C15 S2 -178.7(5) . . . . ?
O1 S2 C15 C20 -31.8(5) . . . . ?
O2 S2 C15 C20 -161.7(4) . . . . ?
C8 S2 C15 C20 85.8(5) . . . . ?
O1 S2 C15 C16 147.9(4) . . . . ?
O2 S2 C15 C16 18.0(5) . . . . ?
C8 S2 C15 C16 -94.5(4) . . . . ?
C20 C15 C16 C17 -1.1(8) . . . . ?
S2 C15 C16 C17 179.2(4) . . . . ?
C11 C12 C13 C14 -0.7(9) . . . . ?
C9 C14 C13 C12 0.8(9) . . . . ?
C9 C10 C11 C12 0.3(9) . . . . ?
C13 C12 C11 C10 0.2(9) . . . . ?
C19 C18 C17 C16 0.6(9) . . . . ?
C21 C18 C17 C16 -178.8(6) . . . . ?
C15 C16 C17 C18 0.0(9) . . . . ?
C15 C20 C19 C18 -1.1(9) . . . . ?
C17 C18 C19 C20 0.0(9) . . . . ?
C21 C18 C19 C20 179.4(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.22
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         2.707
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.097
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1522110'
_audit_update_record             
;
2016-12-10 deposited with the CCDC.
2017-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 N0 O2 S Se'
_chemical_formula_weight         455.45

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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7143(17)
_cell_length_b                   10.963(2)
_cell_length_c                   12.352(3)
_cell_angle_alpha                91.21(3)
_cell_angle_beta                 95.23(3)
_cell_angle_gamma                108.64(3)
_cell_volume                     1111.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2349
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      24.49

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468
_exptl_absorpt_coefficient_mu    1.798
_exptl_absorpt_correction_type   none
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         28.48
_reflns_number_total             5417
_reflns_number_gt                3113
_reflns_threshold_expression     I>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-97 (Sheldrick, 2008)'
_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)+(0.1290P)²+0.0164P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5417
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.2168
_refine_ls_wR_factor_gt          0.1672
_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 0.19455(8) 0.62561(5) 0.58481(4) 0.0903(3) Uani 1 1 d . . .
S1 S 0.54144(11) 0.75271(8) 0.89182(8) 0.0503(3) Uani 1 1 d . . .
C18 C 0.3872(4) 0.7206(3) 0.9805(3) 0.0447(7) Uani 1 1 d . . .
C23 C 0.3456(4) 0.8197(3) 1.0267(3) 0.0511(8) Uani 1 1 d . . .
H23A H 0.3974 0.9047 1.0108 0.061 Uiso 1 1 calc R . .
O1 O 0.6422(3) 0.6757(3) 0.9233(3) 0.0663(8) Uani 1 1 d . . .
C1 C 0.3281(5) 0.9447(4) 0.7736(3) 0.0578(9) Uani 1 1 d . . .
H1A H 0.4307 0.9759 0.7493 0.069 Uiso 1 1 calc R . .
O2 O 0.6177(3) 0.8885(2) 0.8898(3) 0.0629(7) Uani 1 1 d . . .
C7 C 0.3144(5) 0.7217(4) 0.7166(3) 0.0556(9) Uani 1 1 d . . .
C6 C 0.2437(4) 0.8152(4) 0.7634(3) 0.0503(8) Uani 1 1 d . . .
C19 C 0.3124(5) 0.5945(3) 1.0048(3) 0.0555(9) Uani 1 1 d . . .
H19A H 0.3430 0.5282 0.9750 0.067 Uiso 1 1 calc R . .
C21 C 0.1453(5) 0.6643(4) 1.1201(3) 0.0608(10) Uani 1 1 d . . .
C8 C 0.4423(5) 0.6899(4) 0.7583(3) 0.0565(9) Uani 1 1 d . . .
C22 C 0.2250(5) 0.7909(3) 1.0972(3) 0.0535(9) Uani 1 1 d . . .
H22A H 0.1974 0.8573 1.1296 0.064 Uiso 1 1 calc R . .
C2 C 0.2611(6) 1.0289(5) 0.8200(4) 0.0733(12) Uani 1 1 d . . .
H2A H 0.3179 1.1168 0.8262 0.088 Uiso 1 1 calc R . .
C20 C 0.1916(6) 0.5681(4) 1.0740(4) 0.0661(11) Uani 1 1 d . . .
H20A H 0.1401 0.4831 1.0899 0.079 Uiso 1 1 calc R . .
C12 C 0.1535(7) 0.7625(5) 0.5068(4) 0.0746(12) Uani 1 1 d . . .
C10 C 0.4387(7) 0.4575(5) 0.7254(4) 0.0789(13) Uani 1 1 d . . .
H10A H 0.4510 0.4456 0.8029 0.095 Uiso 1 1 calc R . .
H10B H 0.3232 0.4310 0.7012 0.095 Uiso 1 1 calc R . .
C9 C 0.5171(6) 0.5996(4) 0.7042(4) 0.0731(12) Uani 1 1 d . . .
H9A H 0.6320 0.6252 0.7299 0.088 Uiso 1 1 calc R . .
H9B H 0.5084 0.6095 0.6262 0.088 Uiso 1 1 calc R . .
C3 C 0.1088(6) 0.9821(6) 0.8574(4) 0.0795(14) Uani 1 1 d . . .
H3A H 0.0653 1.0384 0.8910 0.095 Uiso 1 1 calc R . .
C5 C 0.0872(5) 0.7699(5) 0.7976(4) 0.0679(11) Uani 1 1 d . . .
H5A H 0.0266 0.6829 0.7881 0.081 Uiso 1 1 calc R . .
C4 C 0.0237(6) 0.8555(6) 0.8453(4) 0.0805(14) Uani 1 1 d . . .
H4A H -0.0791 0.8253 0.8695 0.097 Uiso 1 1 calc R . .
C24 C 0.0138(7) 0.6366(5) 1.1947(5) 0.0967(18) Uani 1 1 d . . .
H24A H -0.0004 0.7159 1.2183 0.145 Uiso 1 1 calc R . .
H24B H 0.0436 0.5947 1.2568 0.145 Uiso 1 1 calc R . .
H24C H -0.0862 0.5813 1.1568 0.145 Uiso 1 1 calc R . .
C11 C 0.5177(9) 0.3743(6) 0.6651(5) 0.114(2) Uani 1 1 d . . .
H11A H 0.4668 0.2854 0.6792 0.172 Uiso 1 1 calc R . .
H11B H 0.6316 0.3996 0.6900 0.172 Uiso 1 1 calc R . .
H11C H 0.5044 0.3854 0.5884 0.172 Uiso 1 1 calc R . .
C13 C -0.0015(9) 0.7642(7) 0.4845(6) 0.115(2) Uani 1 1 d . . .
H13A H -0.0866 0.7020 0.5122 0.138 Uiso 1 1 calc R . .
C15 C 0.0928(17) 0.9452(11) 0.3826(7) 0.153(4) Uani 1 1 d . . .
H15A H 0.0726 1.0081 0.3395 0.183 Uiso 1 1 calc R . .
C17 C 0.2813(10) 0.8514(7) 0.4657(5) 0.109(2) Uani 1 1 d . . .
H17A H 0.3870 0.8488 0.4786 0.131 Uiso 1 1 calc R . .
C14 C -0.0344(13) 0.8574(10) 0.4208(8) 0.135(3) Uani 1 1 d . . .
H14A H -0.1401 0.8591 0.4053 0.162 Uiso 1 1 calc R . .
C16 C 0.2464(15) 0.9467(8) 0.4033(6) 0.141(3) Uani 1 1 d . . .
H16A H 0.3303 1.0108 0.3764 0.169 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 C12 1.911(5) . ?
Se1 C7 1.940(4) . ?
S1 O2 1.425(3) . ?
S1 O1 1.436(3) . ?
S1 C18 1.764(4) . ?
S1 C8 1.804(4) . ?
C18 C23 1.379(5) . ?
C18 C19 1.380(5) . ?
C23 C22 1.389(5) . ?
C23 H23A 0.9300 . ?
C1 C6 1.372(6) . ?
C1 C2 1.380(6) . ?
C1 H1A 0.9300 . ?
C7 C8 1.335(6) . ?
C7 C6 1.485(5) . ?
C6 C5 1.403(5) . ?
C19 C20 1.380(6) . ?
C19 H19A 0.9300 . ?
C21 C20 1.373(6) . ?
C21 C22 1.388(5) . ?
C21 C24 1.495(6) . ?
C8 C9 1.522(5) . ?
C22 H22A 0.9300 . ?
C2 C3 1.387(7) . ?
C2 H2A 0.9300 . ?
C20 H20A 0.9300 . ?
C12 C13 1.360(8) . ?
C12 C17 1.371(9) . ?
C10 C11 1.525(6) . ?
C10 C9 1.527(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C3 C4 1.346(7) . ?
C3 H3A 0.9300 . ?
C5 C4 1.378(7) . ?
C5 H5A 0.9300 . ?
C4 H4A 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.387(11) . ?
C13 H13A 0.9300 . ?
C15 C16 1.334(13) . ?
C15 C14 1.346(13) . ?
C15 H15A 0.9300 . ?
C17 C16 1.404(10) . ?
C17 H17A 0.9300 . ?
C14 H14A 0.9300 . ?
C16 H16A 0.9300 . ?

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
C12 Se1 C7 99.73(18) . . ?
O2 S1 O1 117.85(18) . . ?
O2 S1 C18 109.38(17) . . ?
O1 S1 C18 106.94(17) . . ?
O2 S1 C8 109.36(18) . . ?
O1 S1 C8 106.14(19) . . ?
C18 S1 C8 106.59(17) . . ?
C23 C18 C19 120.8(3) . . ?
C23 C18 S1 120.7(3) . . ?
C19 C18 S1 118.5(3) . . ?
C18 C23 C22 119.1(3) . . ?
C18 C23 H23A 120.5 . . ?
C22 C23 H23A 120.5 . . ?
C6 C1 C2 120.2(4) . . ?
C6 C1 H1A 119.9 . . ?
C2 C1 H1A 119.9 . . ?
C8 C7 C6 127.9(4) . . ?
C8 C7 Se1 116.7(3) . . ?
C6 C7 Se1 115.3(3) . . ?
C1 C6 C5 119.3(4) . . ?
C1 C6 C7 121.4(3) . . ?
C5 C6 C7 119.3(4) . . ?
C20 C19 C18 119.0(3) . . ?
C20 C19 H19A 120.5 . . ?
C18 C19 H19A 120.5 . . ?
C20 C21 C22 118.5(4) . . ?
C20 C21 C24 122.1(4) . . ?
C22 C21 C24 119.4(4) . . ?
C7 C8 C9 126.1(4) . . ?
C7 C8 S1 120.4(3) . . ?
C9 C8 S1 113.4(3) . . ?
C21 C22 C23 120.8(3) . . ?
C21 C22 H22A 119.6 . . ?
C23 C22 H22A 119.6 . . ?
C1 C2 C3 119.9(5) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C21 C20 C19 121.7(4) . . ?
C21 C20 H20A 119.1 . . ?
C19 C20 H20A 119.1 . . ?
C13 C12 C17 121.0(6) . . ?
C13 C12 Se1 120.2(5) . . ?
C17 C12 Se1 118.5(4) . . ?
C11 C10 C9 110.6(5) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C8 C9 C10 114.3(4) . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C4 C5 C6 119.5(4) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 H5A 120.2 . . ?
C3 C4 C5 120.8(4) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 C13 C14 120.9(9) . . ?
C12 C13 H13A 119.6 . . ?
C14 C13 H13A 119.6 . . ?
C16 C15 C14 123.3(9) . . ?
C16 C15 H15A 118.3 . . ?
C14 C15 H15A 118.3 . . ?
C12 C17 C16 117.4(7) . . ?
C12 C17 H17A 121.3 . . ?
C16 C17 H17A 121.3 . . ?
C15 C14 C13 117.3(9) . . ?
C15 C14 H14A 121.3 . . ?
C13 C14 H14A 121.3 . . ?
C15 C16 C17 120.1(9) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?

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
O2 S1 C18 C23 6.5(4) . . . . ?
O1 S1 C18 C23 135.1(3) . . . . ?
C8 S1 C18 C23 -111.7(3) . . . . ?
O2 S1 C18 C19 -171.8(3) . . . . ?
O1 S1 C18 C19 -43.2(4) . . . . ?
C8 S1 C18 C19 70.0(3) . . . . ?
C19 C18 C23 C22 -0.9(6) . . . . ?
S1 C18 C23 C22 -179.2(3) . . . . ?
C12 Se1 C7 C8 -139.6(3) . . . . ?
C12 Se1 C7 C6 45.1(3) . . . . ?
C2 C1 C6 C5 1.8(6) . . . . ?
C2 C1 C6 C7 -178.3(4) . . . . ?
C8 C7 C6 C1 66.7(5) . . . . ?
Se1 C7 C6 C1 -118.6(4) . . . . ?
C8 C7 C6 C5 -113.5(5) . . . . ?
Se1 C7 C6 C5 61.2(4) . . . . ?
C23 C18 C19 C20 1.7(6) . . . . ?
S1 C18 C19 C20 -180.0(3) . . . . ?
C6 C7 C8 C9 -176.0(4) . . . . ?
Se1 C7 C8 C9 9.4(5) . . . . ?
C6 C7 C8 S1 5.2(5) . . . . ?
Se1 C7 C8 S1 -169.43(19) . . . . ?
O2 S1 C8 C7 -66.7(3) . . . . ?
O1 S1 C8 C7 165.2(3) . . . . ?
C18 S1 C8 C7 51.5(3) . . . . ?
O2 S1 C8 C9 114.4(3) . . . . ?
O1 S1 C8 C9 -13.7(3) . . . . ?
C18 S1 C8 C9 -127.5(3) . . . . ?
C20 C21 C22 C23 1.9(6) . . . . ?
C24 C21 C22 C23 -178.8(4) . . . . ?
C18 C23 C22 C21 -1.0(6) . . . . ?
C6 C1 C2 C3 0.7(6) . . . . ?
C22 C21 C20 C19 -1.1(7) . . . . ?
C24 C21 C20 C19 179.6(5) . . . . ?
C18 C19 C20 C21 -0.7(7) . . . . ?
C7 Se1 C12 C13 -114.6(4) . . . . ?
C7 Se1 C12 C17 71.3(5) . . . . ?
C7 C8 C9 C10 -87.2(6) . . . . ?
S1 C8 C9 C10 91.7(5) . . . . ?
C11 C10 C9 C8 178.2(5) . . . . ?
C1 C2 C3 C4 -2.2(7) . . . . ?
C1 C6 C5 C4 -2.9(6) . . . . ?
C7 C6 C5 C4 177.2(4) . . . . ?
C2 C3 C4 C5 1.1(7) . . . . ?
C6 C5 C4 C3 1.4(7) . . . . ?
C17 C12 C13 C14 -1.1(9) . . . . ?
Se1 C12 C13 C14 -175.1(5) . . . . ?
C13 C12 C17 C16 2.3(9) . . . . ?
Se1 C12 C17 C16 176.4(5) . . . . ?
C16 C15 C14 C13 -0.3(14) . . . . ?
C12 C13 C14 C15 0.0(12) . . . . ?
C14 C15 C16 C17 1.6(14) . . . . ?
C12 C17 C16 C15 -2.6(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        28.48
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.085
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1522111'
_audit_update_record             
;
2016-12-10 deposited with the CCDC.
2017-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N0 O2 S Se'
_chemical_formula_weight         377.34

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

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

_cell_length_a                   14.693(3)
_cell_length_b                   13.577(3)
_cell_length_c                   17.032(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.54(3)
_cell_angle_gamma                90.00
_cell_volume                     3387.2(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6374
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.20

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    2.344
_exptl_absorpt_correction_type   none
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14755
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         28.29
_reflns_number_total             4191
_reflns_number_gt                3549
_reflns_threshold_expression     I>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-97 (Sheldrick, 2008)'
_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)+(0.0396P)²+2.3625P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4191
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0773
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.140547(13) 0.077685(15) 0.485193(11) 0.03131(8) Uani 1 1 d . . .
S2 S 0.21282(3) 0.00367(4) 0.23798(3) 0.02667(11) Uani 1 1 d . . .
O1 O 0.19458(11) 0.08012(10) 0.18029(8) 0.0370(3) Uani 1 1 d . . .
O2 O 0.30590(9) -0.02788(11) 0.25495(8) 0.0345(3) Uani 1 1 d . . .
C4 C 0.19374(12) 0.01889(13) 0.39710(10) 0.0263(4) Uani 1 1 d . . .
C5 C 0.16723(12) 0.04551(14) 0.32371(10) 0.0259(4) Uani 1 1 d . . .
H5A H 0.1198 0.0908 0.3173 0.031 Uiso 1 1 calc R . .
C13 C 0.06069(13) -0.08638(14) 0.16994(11) 0.0297(4) Uani 1 1 d . . .
H13A H 0.0370 -0.0233 0.1624 0.036 Uiso 1 1 calc R . .
C6 C 0.07680(13) 0.18453(13) 0.43239(10) 0.0275(4) Uani 1 1 d . . .
C11 C -0.01642(14) 0.17781(15) 0.41492(12) 0.0347(4) Uani 1 1 d . . .
H11A H -0.0480 0.1224 0.4299 0.042 Uiso 1 1 calc R . .
C7 C 0.12395(14) 0.26764(15) 0.41100(12) 0.0344(4) Uani 1 1 d . . .
H7A H 0.1865 0.2727 0.4238 0.041 Uiso 1 1 calc R . .
C12 C 0.14761(13) -0.09984(14) 0.20700(10) 0.0260(4) Uani 1 1 d . . .
C9 C -0.01574(16) 0.33555(17) 0.35239(13) 0.0416(5) Uani 1 1 d . . .
H9A H -0.0468 0.3860 0.3248 0.050 Uiso 1 1 calc R . .
C3 C 0.26427(14) -0.05530(15) 0.41987(11) 0.0331(4) Uani 1 1 d . . .
H3A H 0.2791 -0.0995 0.3772 0.040 Uiso 1 1 calc R . .
C14 C 0.01014(14) -0.16693(17) 0.14464(12) 0.0366(5) Uani 1 1 d . . .
H14A H -0.0480 -0.1578 0.1199 0.044 Uiso 1 1 calc R . .
C1 C 0.27689(18) -0.09987(19) 0.50121(13) 0.0474(6) Uani 1 1 d . . .
H1A H 0.2359 -0.0787 0.5398 0.057 Uiso 1 1 calc R . .
H1B H 0.2954 -0.1684 0.5054 0.057 Uiso 1 1 calc R . .
C10 C -0.06249(15) 0.25391(16) 0.37504(14) 0.0422(5) Uani 1 1 d . . .
H10A H -0.1253 0.2498 0.3635 0.051 Uiso 1 1 calc R . .
C8 C 0.07756(16) 0.34269(16) 0.37068(13) 0.0403(5) Uani 1 1 d . . .
H8A H 0.1090 0.3982 0.3557 0.048 Uiso 1 1 calc R . .
C17 C 0.18299(15) -0.19342(16) 0.21856(13) 0.0390(5) Uani 1 1 d . . .
H17A H 0.2410 -0.2025 0.2435 0.047 Uiso 1 1 calc R . .
C2 C 0.34410(16) -0.02805(19) 0.47633(13) 0.0444(5) Uani 1 1 d . . .
H2A H 0.4038 -0.0526 0.4654 0.053 Uiso 1 1 calc R . .
H2B H 0.3443 0.0371 0.4998 0.053 Uiso 1 1 calc R . .
C15 C 0.04402(16) -0.26137(18) 0.15518(14) 0.0461(6) Uani 1 1 d . . .
C16 C 0.13065(17) -0.27346(17) 0.19250(16) 0.0513(6) Uani 1 1 d . . .
H16A H 0.1541 -0.3367 0.2002 0.062 Uiso 1 1 calc R . .
C18 C -0.0122(2) -0.3490(2) 0.1269(2) 0.0800(10) Uani 1 1 d . . .
H18A H -0.0696 -0.3269 0.1023 0.120 Uiso 1 1 calc R . .
H18B H -0.0228 -0.3906 0.1708 0.120 Uiso 1 1 calc R . .
H18C H 0.0199 -0.3855 0.0894 0.120 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 C6 1.912(2) . ?
Se1 C4 1.9196(17) . ?
S2 O1 1.4397(15) . ?
S2 O2 1.4404(14) . ?
S2 C5 1.7488(18) . ?
S2 C12 1.7583(19) . ?
C4 C5 1.330(3) . ?
C4 C3 1.475(3) . ?
C5 H5A 0.9300 . ?
C13 C14 1.372(3) . ?
C13 C12 1.391(3) . ?
C13 H13A 0.9300 . ?
C6 C11 1.381(3) . ?
C6 C7 1.388(3) . ?
C11 C10 1.384(3) . ?
C11 H11A 0.9300 . ?
C7 C8 1.378(3) . ?
C7 H7A 0.9300 . ?
C12 C17 1.381(3) . ?
C9 C10 1.375(3) . ?
C9 C8 1.385(3) . ?
C9 H9A 0.9300 . ?
C3 C2 1.503(3) . ?
C3 C1 1.510(3) . ?
C3 H3A 0.9800 . ?
C14 C15 1.382(3) . ?
C14 H14A 0.9300 . ?
C1 C2 1.474(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C10 H10A 0.9300 . ?
C8 H8A 0.9300 . ?
C17 C16 1.384(3) . ?
C17 H17A 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C15 C16 1.387(3) . ?
C15 C18 1.506(3) . ?
C16 H16A 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C6 Se1 C4 99.35(8) . . ?
O1 S2 O2 118.29(9) . . ?
O1 S2 C5 105.82(9) . . ?
O2 S2 C5 110.45(9) . . ?
O1 S2 C12 107.69(9) . . ?
O2 S2 C12 107.98(9) . . ?
C5 S2 C12 105.93(9) . . ?
C5 C4 C3 125.47(16) . . ?
C5 C4 Se1 120.98(14) . . ?
C3 C4 Se1 113.55(13) . . ?
C4 C5 S2 126.41(15) . . ?
C4 C5 H5A 116.8 . . ?
S2 C5 H5A 116.8 . . ?
C14 C13 C12 119.50(18) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C11 C6 C7 120.28(19) . . ?
C11 C6 Se1 119.44(15) . . ?
C7 C6 Se1 120.28(15) . . ?
C6 C11 C10 119.65(19) . . ?
C6 C11 H11A 120.2 . . ?
C10 C11 H11A 120.2 . . ?
C8 C7 C6 119.63(19) . . ?
C8 C7 H7A 120.2 . . ?
C6 C7 H7A 120.2 . . ?
C17 C12 C13 120.48(18) . . ?
C17 C12 S2 120.17(15) . . ?
C13 C12 S2 119.35(14) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C4 C3 C2 119.78(18) . . ?
C4 C3 C1 123.21(17) . . ?
C2 C3 C1 58.58(16) . . ?
C4 C3 H3A 114.6 . . ?
C2 C3 H3A 114.6 . . ?
C1 C3 H3A 114.6 . . ?
C13 C14 C15 121.21(19) . . ?
C13 C14 H14A 119.4 . . ?
C15 C14 H14A 119.4 . . ?
C2 C1 C3 60.48(15) . . ?
C2 C1 H1A 117.7 . . ?
C3 C1 H1A 117.7 . . ?
C2 C1 H1B 117.7 . . ?
C3 C1 H1B 117.7 . . ?
H1A C1 H1B 114.8 . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C12 C17 C16 118.9(2) . . ?
C12 C17 H17A 120.5 . . ?
C16 C17 H17A 120.5 . . ?
C1 C2 C3 60.94(15) . . ?
C1 C2 H2A 117.7 . . ?
C3 C2 H2A 117.7 . . ?
C1 C2 H2B 117.7 . . ?
C3 C2 H2B 117.7 . . ?
H2A C2 H2B 114.8 . . ?
C14 C15 C16 118.5(2) . . ?
C14 C15 C18 120.6(2) . . ?
C16 C15 C18 120.9(2) . . ?
C17 C16 C15 121.4(2) . . ?
C17 C16 H16A 119.3 . . ?
C15 C16 H16A 119.3 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C6 Se1 C4 C5 -11.81(18) . . . . ?
C6 Se1 C4 C3 167.95(14) . . . . ?
C3 C4 C5 S2 -3.2(3) . . . . ?
Se1 C4 C5 S2 176.54(10) . . . . ?
O1 S2 C5 C4 -154.80(18) . . . . ?
O2 S2 C5 C4 -25.6(2) . . . . ?
C12 S2 C5 C4 91.04(19) . . . . ?
C4 Se1 C6 C11 102.26(15) . . . . ?
C4 Se1 C6 C7 -77.02(16) . . . . ?
C7 C6 C11 C10 0.8(3) . . . . ?
Se1 C6 C11 C10 -178.45(15) . . . . ?
C11 C6 C7 C8 -1.4(3) . . . . ?
Se1 C6 C7 C8 177.89(15) . . . . ?
C14 C13 C12 C17 -0.2(3) . . . . ?
C14 C13 C12 S2 179.03(14) . . . . ?
O1 S2 C12 C17 142.74(16) . . . . ?
O2 S2 C12 C17 13.95(19) . . . . ?
C5 S2 C12 C17 -104.39(17) . . . . ?
O1 S2 C12 C13 -36.46(17) . . . . ?
O2 S2 C12 C13 -165.25(14) . . . . ?
C5 S2 C12 C13 76.41(16) . . . . ?
C5 C4 C3 C2 124.7(2) . . . . ?
Se1 C4 C3 C2 -55.1(2) . . . . ?
C5 C4 C3 C1 -165.4(2) . . . . ?
Se1 C4 C3 C1 14.8(3) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C4 C3 C1 C2 -107.2(2) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C6 C11 C10 C9 0.4(3) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
C10 C9 C8 C7 0.6(3) . . . . ?
C13 C12 C17 C16 0.2(3) . . . . ?
S2 C12 C17 C16 -179.02(18) . . . . ?
C4 C3 C2 C1 112.9(2) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C13 C14 C15 C18 -179.8(2) . . . . ?
C12 C17 C16 C15 0.1(4) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
C18 C15 C16 C17 179.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.073
