# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_napsesech2oh_3_0m
_database_code_depnum_ccdc_archive 'CCDC 1486467'
_audit_update_record             
;
2016-06-19 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H8 O Se2'
_chemical_formula_sum            'C11 H8 O Se2'
_chemical_formula_weight         314.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   4.6505(5)
_cell_length_b                   13.4476(13)
_cell_length_c                   16.1385(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1009.27(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      21.98

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.067
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    7.286
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.502
_exptl_absorpt_correction_T_max  0.646
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            52654
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         27.45
_reflns_number_total             2297
_reflns_number_gt                1676
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 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)+(0.0994P)²+3.4998P] 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   0.12(5)
_refine_ls_number_reflns         2297
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0783
_refine_ls_wR_factor_ref         0.2135
_refine_ls_wR_factor_gt          0.1945
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_restrained_S_all      1.208
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002

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 0.0374(4) 0.61242(11) 0.29268(9) 0.0724(5) Uani 1 1 d . . .
Se2 Se -0.1834(3) 0.66655(9) 0.16985(9) 0.0644(5) Uani 1 1 d . . .
C11 C -0.065(2) 0.4404(11) -0.0052(6) 0.057(4) Uani 1 1 d . . .
H11 H -0.1382 0.4226 -0.0566 0.068 Uiso 1 1 calc R . .
C1 C -0.070(2) 0.5475(7) 0.1137(6) 0.039(2) Uani 1 1 d . . .
C2 C 0.1216(18) 0.4839(6) 0.1536(6) 0.034(2) Uani 1 1 d . . .
C3 C 0.208(2) 0.5014(8) 0.2383(7) 0.044(2) Uani 1 1 d . . .
C4 C 0.386(3) 0.4399(10) 0.2780(7) 0.057(3) Uani 1 1 d . . .
H4 H 0.4298 0.4510 0.3334 0.068 Uiso 1 1 calc R . .
C5 C 0.509(3) 0.3570(9) 0.2354(9) 0.063(3) Uani 1 1 d . . .
H5 H 0.6447 0.3173 0.2619 0.075 Uiso 1 1 calc R . .
C6 C 0.429(3) 0.3363(9) 0.1565(8) 0.057(3) Uani 1 1 d . . .
H6 H 0.5027 0.2805 0.1299 0.068 Uiso 1 1 calc R . .
C7 C 0.231(2) 0.4001(7) 0.1136(6) 0.038(2) Uani 1 1 d . . .
C8 C 0.123(3) 0.3740(9) 0.0247(8) 0.056(3) Uani 1 1 d . . .
H8 H 0.1821 0.3181 -0.0046 0.067 Uiso 1 1 calc R . .
C9 C -0.1669(19) 0.5245(8) 0.0219(8) 0.047(3) Uani 1 1 d . . .
C10 C -0.363(3) 0.5943(11) -0.0083(9) 0.070(4) Uani 1 1 d . . .
H10A H -0.5458 0.5821 0.0187 0.084 Uiso 1 1 calc R . .
H10B H -0.3902 0.5810 -0.0669 0.084 Uiso 1 1 calc R . .
O1 O -0.301(2) 0.6956(7) 0.0002(9) 0.097(4) Uani 1 1 d . . .
H1 H -0.1323 0.7025 0.0139 0.146 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se1 0.0855(10) 0.0727(9) 0.0591(7) -0.0170(6) 0.0157(7) -0.0182(8)
Se2 0.0609(7) 0.0472(6) 0.0852(10) -0.0041(6) 0.0207(7) 0.0016(6)
C11 0.035(5) 0.118(11) 0.018(4) 0.011(6) -0.006(5) -0.034(7)
C1 0.032(5) 0.042(5) 0.042(5) 0.004(4) 0.019(4) -0.003(4)
C2 0.026(5) 0.031(4) 0.043(5) 0.008(4) -0.001(4) -0.015(3)
C3 0.040(5) 0.043(5) 0.050(6) 0.002(5) 0.004(5) -0.018(5)
C4 0.056(7) 0.076(8) 0.039(6) 0.016(6) -0.016(5) -0.019(6)
C5 0.050(7) 0.061(7) 0.078(9) 0.028(6) -0.003(7) 0.003(6)
C6 0.055(6) 0.044(6) 0.072(8) 0.005(6) 0.004(6) -0.004(5)
C7 0.040(6) 0.029(4) 0.044(5) 0.005(4) 0.005(4) -0.003(4)
C8 0.046(7) 0.050(6) 0.072(8) 0.005(6) 0.027(6) -0.011(5)
C9 0.006(4) 0.039(5) 0.097(9) 0.025(5) 0.014(5) 0.000(4)
C10 0.056(8) 0.095(10) 0.059(8) 0.019(7) 0.002(6) -0.010(7)
O1 0.040(5) 0.071(6) 0.181(12) 0.056(7) -0.031(7) -0.007(5)

_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
Se1 C3 1.905(11) . ?
Se1 Se2 2.348(2) . ?
Se2 C1 1.914(10) . ?
C11 C9 1.301(18) . ?
C11 C8 1.337(19) . ?
C11 H11 0.9300 . ?
C1 C2 1.393(14) . ?
C1 C9 1.580(17) . ?
C2 C7 1.395(14) . ?
C2 C3 1.444(15) . ?
C3 C4 1.332(17) . ?
C4 C5 1.429(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.357(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.437(16) . ?
C6 H6 0.9300 . ?
C7 C8 1.561(18) . ?
C8 H8 0.9300 . ?
C9 C10 1.396(17) . ?
C10 O1 1.400(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
O1 H1 0.8200 . ?

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
C3 Se1 Se2 92.1(3) . . ?
C1 Se2 Se1 91.1(3) . . ?
C9 C11 C8 134.2(12) . . ?
C9 C11 H11 112.9 . . ?
C8 C11 H11 112.9 . . ?
C2 C1 C9 119.7(9) . . ?
C2 C1 Se2 118.1(8) . . ?
C9 C1 Se2 122.0(7) . . ?
C1 C2 C7 121.0(9) . . ?
C1 C2 C3 121.1(9) . . ?
C7 C2 C3 117.9(9) . . ?
C4 C3 C2 121.8(11) . . ?
C4 C3 Se1 121.6(9) . . ?
C2 C3 Se1 116.6(8) . . ?
C3 C4 C5 120.1(11) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.1(12) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.4(12) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 119.5(10) . . ?
C2 C7 C8 119.3(9) . . ?
C6 C7 C8 121.1(10) . . ?
C11 C8 C7 113.0(11) . . ?
C11 C8 H8 123.5 . . ?
C7 C8 H8 123.5 . . ?
C11 C9 C10 134.9(13) . . ?
C11 C9 C1 112.4(9) . . ?
C10 C9 C1 112.4(11) . . ?
C9 C10 O1 119.1(11) . . ?
C9 C10 H10A 107.5 . . ?
O1 C10 H10A 107.5 . . ?
C9 C10 H10B 107.5 . . ?
O1 C10 H10B 107.5 . . ?
H10A C10 H10B 107.0 . . ?
C10 O1 H1 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 Se1 Se2 C1 8.1(4) . . . . ?
Se1 Se2 C1 C2 -9.5(7) . . . . ?
Se1 Se2 C1 C9 175.5(7) . . . . ?
C9 C1 C2 C7 0.2(13) . . . . ?
Se2 C1 C2 C7 -174.9(7) . . . . ?
C9 C1 C2 C3 -178.3(8) . . . . ?
Se2 C1 C2 C3 6.6(11) . . . . ?
C1 C2 C3 C4 178.4(9) . . . . ?
C7 C2 C3 C4 -0.2(14) . . . . ?
C1 C2 C3 Se1 2.0(11) . . . . ?
C7 C2 C3 Se1 -176.5(7) . . . . ?
Se2 Se1 C3 C4 176.4(9) . . . . ?
Se2 Se1 C3 C2 -7.2(7) . . . . ?
C2 C3 C4 C5 3.5(16) . . . . ?
Se1 C3 C4 C5 179.7(9) . . . . ?
C3 C4 C5 C6 -5.0(18) . . . . ?
C4 C5 C6 C7 3.1(18) . . . . ?
C1 C2 C7 C6 179.7(9) . . . . ?
C3 C2 C7 C6 -1.7(13) . . . . ?
C1 C2 C7 C8 -3.5(13) . . . . ?
C3 C2 C7 C8 175.0(8) . . . . ?
C5 C6 C7 C2 0.2(16) . . . . ?
C5 C6 C7 C8 -176.5(10) . . . . ?
C9 C11 C8 C7 3.9(17) . . . . ?
C2 C7 C8 C11 2.1(13) . . . . ?
C6 C7 C8 C11 178.8(10) . . . . ?
C8 C11 C9 C10 -179.7(12) . . . . ?
C8 C11 C9 C1 -6.9(16) . . . . ?
C2 C1 C9 C11 4.4(12) . . . . ?
Se2 C1 C9 C11 179.3(7) . . . . ?
C2 C1 C9 C10 178.9(9) . . . . ?
Se2 C1 C9 C10 -6.2(11) . . . . ?
C11 C9 C10 O1 -138.0(14) . . . . ?
C1 C9 C10 O1 49.3(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.221
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.207
####################################################################### 
# 
# 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_sm103
_database_code_depnum_ccdc_archive 'CCDC 1486468'
_audit_update_record             
;
2016-06-19 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 N O2 Se2'
_chemical_formula_sum            'C15 H17 N O2 Se2'
_chemical_formula_weight         401.22

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   'P 21/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                   12.201(4)
_cell_length_b                   6.3287(16)
_cell_length_c                   19.477(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.736(10)
_cell_angle_gamma                90.00
_cell_volume                     1493.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      28.82

_exptl_crystal_description       prism
_exptl_crystal_colour            orange-yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             198
_exptl_absorpt_coefficient_mu    4.951
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.628
_exptl_absorpt_correction_T_max  0.743
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            70379
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         30.66
_reflns_number_total             4519
_reflns_number_gt                2688
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 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)+(0.0211P)²+4.1451P] 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         4519
_refine_ls_number_parameters     189
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1199
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.001

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
H16 H 0.680(3) 0.062(6) -0.0820(17) 0.034(12) Uiso 1 1 d D . .
H2 H 0.798(3) 0.640(3) -0.183(2) 0.035(11) Uiso 1 1 d D . .
Se1 Se 0.80399(4) -0.13655(7) 0.03410(2) 0.04060(13) Uani 1 1 d . . .
Se2 Se 0.83800(4) -0.39199(8) 0.12535(2) 0.05124(15) Uani 1 1 d . . .
N1 N 0.7238(3) 0.1378(5) -0.05473(16) 0.0325(7) Uani 1 1 d D . .
O2 O 0.7916(3) 0.5124(4) -0.19122(14) 0.0389(7) Uani 1 1 d D . .
O1 O 0.7704(3) -0.0650(4) -0.17394(14) 0.0411(7) Uani 1 1 d . . .
H1 H 0.7265 0.0005 -0.2011 0.062 Uiso 1 1 calc R . .
C1 C 0.7086(3) -0.3106(6) 0.16325(19) 0.0345(9) Uani 1 1 d . . .
C2 C 0.6750(4) -0.4131(7) 0.2192(2) 0.0445(11) Uani 1 1 d . . .
H2A H 0.7108 -0.5359 0.2358 0.053 Uiso 1 1 calc R . .
C3 C 0.5871(4) -0.3331(8) 0.2515(2) 0.0514(12) Uani 1 1 d . . .
H3 H 0.5652 -0.4027 0.2896 0.062 Uiso 1 1 calc R . .
C4 C 0.5334(4) -0.1551(8) 0.2276(2) 0.0454(11) Uani 1 1 d . . .
H4 H 0.4771 -0.1012 0.2508 0.054 Uiso 1 1 calc R . .
C5 C 0.5620(3) -0.0503(7) 0.16800(19) 0.0332(9) Uani 1 1 d . . .
C6 C 0.6516(3) -0.1306(6) 0.13511(17) 0.0281(7) Uani 1 1 d . . .
C7 C 0.6813(3) -0.0252(6) 0.07523(18) 0.0270(8) Uani 1 1 d . . .
C8 C 0.6242(3) 0.1479(6) 0.04814(19) 0.0312(8) Uani 1 1 d . . .
C9 C 0.5359(3) 0.2236(7) 0.0822(2) 0.0424(10) Uani 1 1 d . . .
H9 H 0.4965 0.3409 0.0644 0.051 Uiso 1 1 calc R . .
C10 C 0.5069(3) 0.1306(7) 0.1401(2) 0.0425(10) Uani 1 1 d . . .
H10 H 0.4495 0.1874 0.1616 0.051 Uiso 1 1 calc R . .
C11 C 0.6541(3) 0.2648(6) -0.0139(2) 0.0382(10) Uani 1 1 d . . .
H11A H 0.5870 0.3042 -0.0429 0.046 Uiso 1 1 calc R . .
H11B H 0.6929 0.3935 0.0010 0.046 Uiso 1 1 calc R . .
C12 C 0.7960(3) 0.2492(6) -0.09817(18) 0.0272(8) Uani 1 1 d . . .
C13 C 0.8487(3) 0.0781(6) -0.1395(2) 0.0360(9) Uani 1 1 d . . .
H13A H 0.8890 0.1458 -0.1735 0.043 Uiso 1 1 calc R . .
H13B H 0.9013 -0.0011 -0.1083 0.043 Uiso 1 1 calc R . .
C14 C 0.8876(3) 0.3628(7) -0.0540(2) 0.0394(9) Uani 1 1 d . . .
H14A H 0.8566 0.4708 -0.0275 0.059 Uiso 1 1 calc R . .
H14B H 0.9368 0.4260 -0.0831 0.059 Uiso 1 1 calc R . .
H14C H 0.9276 0.2637 -0.0232 0.059 Uiso 1 1 calc R . .
C15 C 0.7264(3) 0.4040(6) -0.1461(2) 0.0365(9) Uani 1 1 d . . .
H15A H 0.6681 0.3267 -0.1735 0.044 Uiso 1 1 calc R . .
H15B H 0.6922 0.5064 -0.1183 0.044 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se1 0.0495(3) 0.0374(2) 0.0378(2) 0.00481(19) 0.01721(18) 0.0168(2)
Se2 0.0622(3) 0.0508(3) 0.0424(3) 0.0136(2) 0.0133(2) 0.0269(2)
N1 0.049(2) 0.0226(15) 0.0264(16) 0.0024(14) 0.0067(14) -0.0014(15)
O2 0.063(2) 0.0215(14) 0.0341(15) 0.0017(12) 0.0131(14) -0.0037(13)
O1 0.064(2) 0.0256(14) 0.0341(15) -0.0041(12) 0.0077(14) -0.0049(13)
C1 0.043(2) 0.032(2) 0.0282(19) -0.0028(16) 0.0005(17) 0.0012(17)
C2 0.052(3) 0.045(3) 0.035(2) 0.0089(19) -0.0023(19) -0.006(2)
C3 0.056(3) 0.065(3) 0.033(2) 0.008(2) 0.009(2) -0.016(3)
C4 0.039(2) 0.064(3) 0.034(2) -0.003(2) 0.0108(18) -0.011(2)
C5 0.028(2) 0.043(2) 0.0294(19) -0.0025(17) 0.0048(15) -0.0036(17)
C6 0.0297(19) 0.0288(18) 0.0251(17) -0.0038(15) -0.0001(14) -0.0012(16)
C7 0.0269(19) 0.0295(19) 0.0249(18) -0.0042(15) 0.0049(14) 0.0023(15)
C8 0.031(2) 0.032(2) 0.0313(19) -0.0009(16) 0.0062(15) 0.0045(17)
C9 0.038(2) 0.040(2) 0.052(3) 0.004(2) 0.012(2) 0.0117(19)
C10 0.030(2) 0.052(3) 0.049(2) -0.001(2) 0.0169(18) 0.007(2)
C11 0.043(2) 0.031(2) 0.043(2) 0.0090(18) 0.0143(19) 0.0135(18)
C12 0.033(2) 0.0228(18) 0.0260(18) -0.0013(14) 0.0057(15) 0.0038(15)
C13 0.044(2) 0.029(2) 0.036(2) -0.0021(17) 0.0094(18) 0.0053(17)
C14 0.038(2) 0.039(2) 0.040(2) -0.0093(19) 0.0014(17) 0.0015(19)
C15 0.047(2) 0.0245(19) 0.039(2) 0.0037(16) 0.0083(18) -0.0004(17)

_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
Se1 C7 1.913(3) . ?
Se1 Se2 2.4023(7) . ?
Se2 C1 1.891(4) . ?
N1 C11 1.470(5) . ?
N1 C12 1.472(5) . ?
N1 H16 0.856(18) . ?
O2 C15 1.428(5) . ?
O2 H2 0.824(18) . ?
O1 C13 1.426(5) . ?
O1 H1 0.8200 . ?
C1 C2 1.372(6) . ?
C1 C6 1.411(5) . ?
C2 C3 1.400(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.357(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.416(6) . ?
C4 H4 0.9300 . ?
C5 C10 1.405(6) . ?
C5 C6 1.424(5) . ?
C6 C7 1.427(5) . ?
C7 C8 1.371(5) . ?
C8 C9 1.414(5) . ?
C8 C11 1.498(5) . ?
C9 C10 1.354(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C14 1.510(5) . ?
C12 C13 1.534(5) . ?
C12 C15 1.539(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 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
C7 Se1 Se2 90.79(11) . . ?
C1 Se2 Se1 91.48(12) . . ?
C11 N1 C12 118.2(3) . . ?
C11 N1 H16 106(3) . . ?
C12 N1 H16 107(3) . . ?
C15 O2 H2 114(3) . . ?
C13 O1 H1 109.5 . . ?
C2 C1 C6 120.7(4) . . ?
C2 C1 Se2 121.5(3) . . ?
C6 C1 Se2 117.7(3) . . ?
C1 C2 C3 120.1(4) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C10 C5 C4 123.1(4) . . ?
C10 C5 C6 118.3(3) . . ?
C4 C5 C6 118.5(4) . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 C7 122.2(3) . . ?
C5 C6 C7 118.9(3) . . ?
C8 C7 C6 121.5(3) . . ?
C8 C7 Se1 121.4(3) . . ?
C6 C7 Se1 117.2(3) . . ?
C7 C8 C9 118.1(3) . . ?
C7 C8 C11 123.0(3) . . ?
C9 C8 C11 118.9(3) . . ?
C10 C9 C8 122.1(4) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C5 121.1(4) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
N1 C11 C8 112.2(3) . . ?
N1 C11 H11A 109.2 . . ?
C8 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C8 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N1 C12 C14 110.7(3) . . ?
N1 C12 C13 106.2(3) . . ?
C14 C12 C13 107.9(3) . . ?
N1 C12 C15 109.2(3) . . ?
C14 C12 C15 111.2(3) . . ?
C13 C12 C15 111.5(3) . . ?
O1 C13 C12 113.4(3) . . ?
O1 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
O1 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 C12 111.8(3) . . ?
O2 C15 H15A 109.3 . . ?
C12 C15 H15A 109.3 . . ?
O2 C15 H15B 109.3 . . ?
C12 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 Se1 Se2 C1 5.97(16) . . . . ?
Se1 Se2 C1 C2 176.4(3) . . . . ?
Se1 Se2 C1 C6 -8.0(3) . . . . ?
C6 C1 C2 C3 -3.5(6) . . . . ?
Se2 C1 C2 C3 172.0(3) . . . . ?
C1 C2 C3 C4 0.6(7) . . . . ?
C2 C3 C4 C5 2.5(7) . . . . ?
C3 C4 C5 C10 178.0(4) . . . . ?
C3 C4 C5 C6 -2.6(6) . . . . ?
C2 C1 C6 C5 3.3(6) . . . . ?
Se2 C1 C6 C5 -172.3(3) . . . . ?
C2 C1 C6 C7 -177.4(4) . . . . ?
Se2 C1 C6 C7 7.0(5) . . . . ?
C10 C5 C6 C1 179.1(4) . . . . ?
C4 C5 C6 C1 -0.3(5) . . . . ?
C10 C5 C6 C7 -0.2(5) . . . . ?
C4 C5 C6 C7 -179.6(3) . . . . ?
C1 C6 C7 C8 179.2(4) . . . . ?
C5 C6 C7 C8 -1.4(5) . . . . ?
C1 C6 C7 Se1 -0.5(5) . . . . ?
C5 C6 C7 Se1 178.9(3) . . . . ?
Se2 Se1 C7 C8 176.0(3) . . . . ?
Se2 Se1 C7 C6 -4.3(3) . . . . ?
C6 C7 C8 C9 1.6(6) . . . . ?
Se1 C7 C8 C9 -178.8(3) . . . . ?
C6 C7 C8 C11 179.0(4) . . . . ?
Se1 C7 C8 C11 -1.3(5) . . . . ?
C7 C8 C9 C10 0.0(6) . . . . ?
C11 C8 C9 C10 -177.6(4) . . . . ?
C8 C9 C10 C5 -1.7(7) . . . . ?
C4 C5 C10 C9 -178.9(4) . . . . ?
C6 C5 C10 C9 1.8(6) . . . . ?
C12 N1 C11 C8 -155.2(3) . . . . ?
C7 C8 C11 N1 18.9(6) . . . . ?
C9 C8 C11 N1 -163.7(4) . . . . ?
C11 N1 C12 C14 68.7(4) . . . . ?
C11 N1 C12 C13 -174.4(3) . . . . ?
C11 N1 C12 C15 -54.0(4) . . . . ?
N1 C12 C13 O1 50.7(4) . . . . ?
C14 C12 C13 O1 169.5(3) . . . . ?
C15 C12 C13 O1 -68.1(4) . . . . ?
N1 C12 C15 O2 -178.2(3) . . . . ?
C14 C12 C15 O2 59.4(4) . . . . ?
C13 C12 C15 O2 -61.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        30.66
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.112
