# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_PBS
_database_code_depnum_ccdc_archive 'CCDC 1516438'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2017-03-02 downloaded from the CCDC.
;
_audit_creation_date             2016-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H7 N2 O2 Se, C10 H10 N2 O2 Se'
_chemical_formula_sum            'C20 H20 N4 O4 Se2'
_chemical_formula_weight         538.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   21.9362(9)
_cell_length_b                   4.53698(16)
_cell_length_c                   23.8161(11)
_cell_angle_alpha                90
_cell_angle_beta                 112.119(5)
_cell_angle_gamma                90
_cell_volume                     2195.84(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2127
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.6698
_cell_measurement_theta_min      3.4646
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.503
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   acicular
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       acicular
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6476
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        62.762
_diffrn_reflns_theta_max         62.762
_diffrn_reflns_theta_min         3.468
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0288
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -83.00  -53.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.9934  178.0000   60.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega   14.00  102.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   57.0000    0.0000 88

#__ type_ start__ end____ width___ exp.time_
  3 omega   49.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934 -178.0000  -30.0000 61

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934  178.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
  5 omega   29.00   56.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   34.00  112.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000   60.0000 78

#__ type_ start__ end____ width___ exp.time_
  7 omega   67.00  157.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
  8 omega   37.00  102.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000    0.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega   24.00   63.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
 10 omega  139.00  164.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   21.00   66.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000    0.0000 45

#__ type_ start__ end____ width___ exp.time_
 12 omega   68.00  110.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000  -90.0000 42

#__ type_ start__ end____ width___ exp.time_
 13 omega   28.00   60.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
 14 omega   19.00   64.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000   30.0000 45
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0472722000
_diffrn_orient_matrix_UB_12      0.0784249000
_diffrn_orient_matrix_UB_13      -0.0647133000
_diffrn_orient_matrix_UB_21      -0.0440097000
_diffrn_orient_matrix_UB_22      -0.2638679000
_diffrn_orient_matrix_UB_23      0.0005657000
_diffrn_orient_matrix_UB_31      -0.0396239000
_diffrn_orient_matrix_UB_32      0.1990687000
_diffrn_orient_matrix_UB_33      0.0262453000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2859
_reflns_number_total             3471
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.899
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3471
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0895P)²+0.3005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1435
_refine_ls_wR_factor_ref         0.1594
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C13-C12 \\sim C8_$1-C9_$1
 with sigma of 0.005
 Se1-N4 \\sim N1-Se2
 with sigma of 0.005
 N4-Se1 \\sim Se2-N1
 with sigma of 0.005
3.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C9(H9a,H9b), C12(H12a,H12b), C13(H13a,H13b)
3.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C20(H20)
3.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0538(3) -0.8624(13) 0.1636(2) 0.0500(12) Uani 1 1 d . . . . .
C2 C 0.0010(3) -1.0191(12) 0.1192(2) 0.0494(12) Uani 1 1 d . . . . .
C3 C -0.0407(3) -1.2005(14) 0.1376(3) 0.0598(15) Uani 1 1 d . . . . .
C4 C -0.0295(3) -1.2180(14) 0.1977(3) 0.0612(15) Uani 1 1 d . . . . .
C5 C 0.0240(3) -1.0593(17) 0.2423(3) 0.0663(16) Uani 1 1 d . . . . .
C6 C 0.0647(3) -0.8902(17) 0.2266(3) 0.0658(16) Uani 1 1 d . . . . .
C7 C -0.0720(3) -1.3936(17) 0.2211(3) 0.0713(17) Uani 1 1 d . . . . .
C8 C -0.1682(4) -1.675(2) 0.1958(4) 0.102(3) Uani 1 1 d . . . . .
H8A H -0.148175 -1.842986 0.221295 0.122 Uiso 1 1 calc R . . . .
H8B H -0.184348 -1.540964 0.218778 0.122 Uiso 1 1 calc R . . . .
C9 C -0.2208(5) -1.770(3) 0.1432(5) 0.148(5) Uani 1 1 d . . . . .
H9A H -0.205156 -1.923708 0.123647 0.177 Uiso 1 1 calc R . . . .
H9B H -0.235512 -1.606190 0.115122 0.177 Uiso 1 1 calc R . . . .
C10 C -0.2791(5) -1.888(4) 0.1571(6) 0.168(6) Uani 1 1 d . . . . .
H10A H -0.264525 -2.046110 0.185785 0.253 Uiso 1 1 calc GR . . . .
H10B H -0.312493 -1.958628 0.120367 0.253 Uiso 1 1 calc GR . . . .
H10C H -0.296813 -1.732334 0.173715 0.253 Uiso 1 1 calc GR . . . .
C11 C 0.5558(4) 0.760(2) 0.0879(5) 0.095(3) Uani 1 1 d . . . . .
H11A H 0.540465 0.910639 0.057541 0.142 Uiso 1 1 calc GR . . . .
H11B H 0.585694 0.632116 0.078531 0.142 Uiso 1 1 calc GR . . . .
H11C H 0.578143 0.848560 0.126816 0.142 Uiso 1 1 calc GR . . . .
C12 C 0.4978(4) 0.5814(18) 0.0889(4) 0.086(2) Uani 1 1 d . . . . .
H12A H 0.482794 0.452803 0.053808 0.104 Uiso 1 1 calc R . . . .
H12B H 0.512484 0.457559 0.124752 0.104 Uiso 1 1 calc R . . . .
C13 C 0.4437(4) 0.7539(17) 0.0889(4) 0.087(2) Uani 1 1 d . . . . .
H13A H 0.425270 0.861943 0.051122 0.104 Uiso 1 1 calc R . . . .
H13B H 0.458820 0.895817 0.121794 0.104 Uiso 1 1 calc R . . . .
C14 C 0.3462(3) 0.4596(15) 0.0468(3) 0.0682(16) Uani 1 1 d . . . . .
C15 C 0.2995(3) 0.2595(13) 0.0617(3) 0.0562(14) Uani 1 1 d . . . . .
C16 C 0.2453(3) 0.1413(16) 0.0131(3) 0.0674(17) Uani 1 1 d . . . . .
H16 H 0.239900 0.191656 -0.026379 0.081 Uiso 1 1 calc R . . . .
C17 C 0.2013(3) -0.0418(16) 0.0219(3) 0.0675(16) Uani 1 1 d . . . . .
H17 H 0.165444 -0.112192 -0.010779 0.081 Uiso 1 1 calc R . . . .
C18 C 0.2109(3) -0.1262(13) 0.0831(2) 0.0503(12) Uani 1 1 d . . . . .
C19 C 0.2655(2) -0.0131(11) 0.1313(2) 0.0457(11) Uani 1 1 d . . . . .
C20 C 0.3104(3) 0.1863(14) 0.1198(3) 0.0553(14) Uani 1 1 d . . . . .
H20 H 0.346212 0.263405 0.151556 0.066 Uiso 1 1 calc R . . . .
N2 N -0.0048(2) -0.9875(12) 0.0620(2) 0.0597(12) Uani 1 1 d . . . . .
N3 N 0.2716(2) -0.0932(11) 0.1868(2) 0.0579(12) Uani 1 1 d . . . . .
N4 N 0.1699(2) -0.3146(10) 0.0979(2) 0.0544(11) Uani 1 1 d . . . . .
O1 O -0.0655(3) -1.4088(17) 0.2727(3) 0.111(2) Uani 1 1 d . . . . .
O2 O -0.1200(2) -1.5270(13) 0.1773(2) 0.0877(15) Uani 1 1 d . . . . .
O3 O 0.3929(2) 0.5672(11) 0.0962(2) 0.0780(13) Uani 1 1 d . . . . .
O4 O 0.3408(3) 0.5112(15) -0.0041(3) 0.0982(17) Uani 1 1 d . . . . .
Se1 Se 0.05849(3) -0.73816(15) 0.06195(3) 0.0569(2) Uani 1 1 d . . . . .
Se2 Se 0.20414(3) -0.33089(14) 0.17829(2) 0.0540(2) Uani 1 1 d . . . . .
N1 N 0.0882(2) -0.7033(10) 0.1415(2) 0.0568(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.429(8) . ?
C1 C6 1.434(8) . ?
C1 N1 1.291(7) . ?
C2 C3 1.418(8) . ?
C2 N2 1.328(7) . ?
C3 C4 1.360(9) . ?
C4 C5 1.445(10) . ?
C4 C7 1.486(9) . ?
C5 C6 1.333(10) . ?
C7 O1 1.184(8) . ?
C7 O2 1.318(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.413(10) . ?
C8 O2 1.455(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.533(14) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11 C12 1.517(11) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.421(9) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 O3 1.461(8) . ?
C14 C15 1.508(9) . ?
C14 O3 1.329(8) . ?
C14 O4 1.196(8) . ?
C15 C16 1.415(9) . ?
C15 C20 1.353(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.349(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.443(8) . ?
C18 C19 1.407(7) . ?
C18 N4 1.380(7) . ?
C19 C20 1.439(8) . ?
C19 N3 1.326(7) . ?
C20 H20 0.9300 . ?
N2 Se1 1.791(5) . ?
N3 Se2 1.780(5) . ?
N4 Se2 1.776(5) . ?
Se1 N1 1.764(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
C2 C1 C6 120.0(5) . . ?
N1 C1 C2 114.4(5) . . ?
N1 C1 C6 125.6(6) . . ?
C3 C2 C1 119.9(5) . . ?
N2 C2 C1 116.3(5) . . ?
N2 C2 C3 123.8(5) . . ?
C4 C3 C2 118.4(6) . . ?
C3 C4 C5 121.4(6) . . ?
C3 C4 C7 122.4(6) . . ?
C5 C4 C7 116.2(6) . . ?
C6 C5 C4 121.6(5) . . ?
C5 C6 C1 118.6(6) . . ?
O1 C7 C4 125.0(7) . . ?
O1 C7 O2 122.9(7) . . ?
O2 C7 C4 112.0(6) . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 H8A 110.0 . . ?
C9 C8 H8B 110.0 . . ?
C9 C8 O2 108.4(8) . . ?
O2 C8 H8A 110.0 . . ?
O2 C8 H8B 110.0 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C8 C9 C10 112.6(10) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
C11 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 C11 114.4(7) . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 O3 110.8(6) . . ?
H13A C13 H13B 108.1 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C14 C15 112.2(6) . . ?
O4 C14 C15 122.7(7) . . ?
O4 C14 O3 125.1(6) . . ?
C16 C15 C14 118.1(6) . . ?
C20 C15 C14 120.9(6) . . ?
C20 C15 C16 121.0(6) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 C15 122.4(6) . . ?
C17 C16 H16 118.8 . . ?
C16 C17 H17 120.7 . . ?
C16 C17 C18 118.6(6) . . ?
C18 C17 H17 120.7 . . ?
C19 C18 C17 119.0(5) . . ?
N4 C18 C17 124.1(5) . . ?
N4 C18 C19 116.9(5) . . ?
C18 C19 C20 120.4(5) . . ?
N3 C19 C18 116.7(5) . . ?
N3 C19 C20 122.9(5) . . ?
C15 C20 C19 118.7(5) . . ?
C15 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C2 N2 Se1 107.1(4) . . ?
C19 N3 Se2 106.6(4) . . ?
C18 N4 Se2 104.4(3) . . ?
C7 O2 C8 115.3(6) . . ?
C14 O3 C13 118.4(6) . . ?
N1 Se1 N2 91.7(2) . . ?
N4 Se2 N3 95.3(2) . . ?
C1 N1 Se1 110.5(4) . . ?

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
C1 C2 C3 C4 0.6(9) . . . . ?
C1 C2 N2 Se1 -1.4(6) . . . . ?
C2 C1 C6 C5 -1.3(9) . . . . ?
C2 C1 N1 Se1 -0.9(6) . . . . ?
C2 C3 C4 C5 -0.7(9) . . . . ?
C2 C3 C4 C7 177.7(6) . . . . ?
C2 N2 Se1 N1 0.8(4) . . . . ?
C3 C2 N2 Se1 179.9(5) . . . . ?
C3 C4 C5 C6 -0.3(11) . . . . ?
C3 C4 C7 O1 -177.6(8) . . . . ?
C3 C4 C7 O2 0.5(10) . . . . ?
C4 C5 C6 C1 1.3(10) . . . . ?
C4 C7 O2 C8 -173.1(7) . . . . ?
C5 C4 C7 O1 0.9(11) . . . . ?
C5 C4 C7 O2 179.0(6) . . . . ?
C6 C1 C2 C3 0.4(8) . . . . ?
C6 C1 C2 N2 -178.3(6) . . . . ?
C6 C1 N1 Se1 179.1(5) . . . . ?
C7 C4 C5 C6 -178.8(7) . . . . ?
C9 C8 O2 C7 171.8(9) . . . . ?
C11 C12 C13 O3 -174.2(7) . . . . ?
C12 C13 O3 C14 -89.6(9) . . . . ?
C14 C15 C16 C17 179.4(7) . . . . ?
C14 C15 C20 C19 -178.0(5) . . . . ?
C15 C14 O3 C13 177.1(5) . . . . ?
C15 C16 C17 C18 -1.8(11) . . . . ?
C16 C15 C20 C19 -0.5(9) . . . . ?
C16 C17 C18 C19 0.5(9) . . . . ?
C16 C17 C18 N4 -179.2(6) . . . . ?
C17 C18 C19 C20 0.7(8) . . . . ?
C17 C18 C19 N3 178.9(5) . . . . ?
C17 C18 N4 Se2 -178.7(5) . . . . ?
C18 C19 C20 C15 -0.7(8) . . . . ?
C18 C19 N3 Se2 0.3(6) . . . . ?
C18 N4 Se2 N3 -1.2(4) . . . . ?
C19 C18 N4 Se2 1.6(6) . . . . ?
C19 N3 Se2 N4 0.5(4) . . . . ?
C20 C15 C16 C17 1.8(10) . . . . ?
C20 C19 N3 Se2 178.5(4) . . . . ?
N2 C2 C3 C4 179.2(6) . . . . ?
N2 Se1 N1 C1 0.1(4) . . . . ?
N3 C19 C20 C15 -178.8(6) . . . . ?
N4 C18 C19 C20 -179.6(5) . . . . ?
N4 C18 C19 N3 -1.4(7) . . . . ?
O1 C7 O2 C8 5.1(12) . . . . ?
O2 C8 C9 C10 -171.4(11) . . . . ?
O3 C14 C15 C16 176.9(6) . . . . ?
O3 C14 C15 C20 -5.5(9) . . . . ?
O4 C14 C15 C16 -3.3(10) . . . . ?
O4 C14 C15 C20 174.3(7) . . . . ?
O4 C14 O3 C13 -2.6(11) . . . . ?
N1 C1 C2 C3 -179.7(5) . . . . ?
N1 C1 C2 N2 1.6(8) . . . . ?
N1 C1 C6 C5 178.7(6) . . . . ?

_shelx_SHELXL_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_IBS
_database_code_depnum_ccdc_archive 'CCDC 1516447'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2017-03-02 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H10 N2 O2 Se'
_chemical_formula_sum            'C10 H10 N2 O2 Se'
_chemical_formula_weight         269.16
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   16.3500(7)
_cell_length_b                   4.6387(2)
_cell_length_c                   14.6202(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.521(4)
_cell_angle_gamma                90.00
_cell_volume                     1082.46(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1883
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.5745
_cell_measurement_theta_min      3.0937
_exptl_absorpt_coefficient_mu    4.567
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 12
_diffrn_standards_interval_time  2
_diffrn_reflns_number            3016
_diffrn_reflns_theta_full        62.66
_diffrn_reflns_theta_max         62.66
_diffrn_reflns_theta_min         5.54
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'

_diffrn_standards_number         3314
_reflns_number_gt                1539
_reflns_number_total             1718
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1718
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0269
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0438P)²+0.2606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0739
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.37490(16) 0.3907(5) 0.92825(17) 0.0424(6) Uani 1 d . . .
C2 C 0.31803(17) 0.5089(6) 0.97936(18) 0.0508(6) Uani 1 d . . .
H2 H 0.3221 0.4586 1.0418 0.061 Uiso 1 calc . . R
C3 C 0.25866(18) 0.6931(6) 0.93706(18) 0.0510(6) Uani 1 d . . .
H3 H 0.2218 0.7697 0.9709 0.061 Uiso 1 calc . . R
C4 C 0.25046(16) 0.7758(6) 0.84052(17) 0.0449(6) Uani 1 d . . .
C5 C 0.30349(17) 0.6678(6) 0.78918(18) 0.0465(6) Uani 1 d . . .
H5 H 0.2980 0.7223 0.7269 0.056 Uiso 1 calc . . R
C6 C 0.36714(16) 0.4717(6) 0.83109(17) 0.0424(6) Uani 1 d . . .
C7 C 0.18175(17) 0.9822(6) 0.80165(18) 0.0483(6) Uani 1 d . . .
C8 C 0.10861(18) 1.2245(7) 0.66431(19) 0.0533(7) Uani 1 d . . .
H8 H 0.1063 1.3876 0.7063 0.064 Uiso 1 calc . . R
C9 C 0.0253(2) 1.0732(8) 0.6434(2) 0.0711(9) Uani 1 d . . .
H9A H 0.0274 0.9143 0.6019 0.107 Uiso 1 calc . . GR
H9B H -0.0175 1.2058 0.6142 0.107 Uiso 1 calc . . GR
H9C H 0.0130 1.0029 0.7007 0.107 Uiso 1 calc . . GR
C10 C 0.1360(2) 1.3298(8) 0.5783(2) 0.0760(10) Uani 1 d . . .
H10A H 0.1894 1.4233 0.5965 0.114 Uiso 1 calc . . GR
H10B H 0.0954 1.4643 0.5453 0.114 Uiso 1 calc . . GR
H10C H 0.1405 1.1693 0.5383 0.114 Uiso 1 calc . . GR
N1 N 0.43580(14) 0.2095(5) 0.96270(14) 0.0474(5) Uani 1 d . . .
N2 N 0.42247(15) 0.3533(5) 0.78764(15) 0.0521(6) Uani 1 d . . .
O1 O 0.13831(14) 1.0935(5) 0.84760(14) 0.0659(6) Uani 1 d . . .
O2 O 0.17384(11) 1.0236(4) 0.70975(12) 0.0529(5) Uani 1 d . . .
Se1 Se 0.488533(17) 0.12601(7) 0.871133(18) 0.04970(14) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.423(4) . ?
C1 C6 1.448(3) . ?
C1 N1 1.317(3) . ?
C2 C3 1.340(4) . ?
C3 C4 1.440(3) . ?
C4 C5 1.359(4) . ?
C4 C7 1.492(4) . ?
C5 C6 1.418(4) . ?
C6 N2 1.332(3) . ?
C7 O1 1.196(3) . ?
C7 O2 1.336(3) . ?
C8 C9 1.503(4) . ?
C8 C10 1.504(4) . ?
C8 O2 1.463(3) . ?
N1 Se1 1.785(2) . ?
N2 Se1 1.788(2) . ?

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
C2 C1 C6 119.1(2) . . ?
N1 C1 C2 124.8(2) . . ?
N1 C1 C6 116.0(2) . . ?
C3 C2 C1 119.6(2) . . ?
C2 C3 C4 121.8(2) . . ?
C3 C4 C7 116.5(2) . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 C7 122.9(2) . . ?
C4 C5 C6 119.6(2) . . ?
C5 C6 C1 119.4(2) . . ?
N2 C6 C1 115.9(2) . . ?
N2 C6 C5 124.7(2) . . ?
O1 C7 C4 123.6(2) . . ?
O1 C7 O2 124.3(3) . . ?
O2 C7 C4 112.1(2) . . ?
C9 C8 C10 113.7(3) . . ?
O2 C8 C9 109.5(3) . . ?
O2 C8 C10 105.5(2) . . ?
C1 N1 Se1 107.44(16) . . ?
C6 N2 Se1 106.85(17) . . ?
C7 O2 C8 116.8(2) . . ?
N1 Se1 N2 93.76(10) . . ?

####################################################################### 
# 
# 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_BBS
_database_code_depnum_ccdc_archive 'CCDC 1517017'
_audit_update_record             
;
2016-11-12 deposited with the CCDC.
2017-03-02 downloaded from the CCDC.
;
_audit_creation_date             2016-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H12 N2 O2 Se'
_chemical_formula_sum            'C11 H12 N2 O2 Se'
_chemical_formula_weight         283.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   23.715(3)
_cell_length_b                   4.6936(3)
_cell_length_c                   24.377(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.245(14)
_cell_angle_gamma                90
_cell_volume                     2412.4(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2473
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.6684
_cell_measurement_theta_min      3.5280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.129
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7208
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        NONE
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        62.756
_diffrn_reflns_theta_max         62.756
_diffrn_reflns_theta_min         3.531
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3177
_reflns_number_total             3822
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3822
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.181
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+2.4981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1414
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C21-C22
 1.52 with sigma of 0.005
 Se1-N3 \\sim Se2-N2
 with sigma of 0.005
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C2(H2A,H2B), C20(H20A,H20B), C19(H19A,H19B),
 C21(H21A,H21B)
3.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C11(H11), C17(H17), C16(H16), C8(H8), C7(H7)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.20071(3) 0.19262(13) 0.17693(3) 0.0631(2) Uani 1 1 d . . . . .
Se2 Se 0.05887(3) -0.24052(13) 0.06128(3) 0.0640(2) Uani 1 1 d . . . . .
C10 C 0.2497(3) 0.5082(11) 0.1272(2) 0.0564(13) Uani 1 1 d . . . . .
N4 N 0.0039(2) -0.4934(11) 0.0633(2) 0.0661(12) Uani 1 1 d . . . . .
N3 N 0.0936(2) -0.1920(10) 0.1427(2) 0.0674(12) Uani 1 1 d . . . . .
N2 N 0.1619(2) 0.1865(10) 0.0939(2) 0.0633(12) Uani 1 1 d . . . . .
C12 C 0.0665(3) -0.3506(11) 0.1660(2) 0.0544(12) Uani 1 1 d . . . . .
C14 C -0.0191(3) -0.7006(13) 0.1427(3) 0.0683(15) Uani 1 1 d . . . . .
H14 H -0.0525 -0.8110 0.1148 0.082 Uiso 1 1 calc R . . . .
C13 C 0.0151(3) -0.5176(11) 0.1220(2) 0.0562(13) Uani 1 1 d . . . . .
C11 C 0.2878(3) 0.7028(12) 0.1135(3) 0.0634(14) Uani 1 1 d . . . . .
H11 H 0.3225 0.7910 0.1453 0.076 Uiso 1 1 calc R . . . .
C17 C 0.0830(3) -0.3680(14) 0.2297(3) 0.0709(16) Uani 1 1 d . . . . .
H17 H 0.1163 -0.2604 0.2586 0.085 Uiso 1 1 calc R . . . .
C9 C 0.1965(3) 0.3687(12) 0.0786(2) 0.0578(13) Uani 1 1 d . . . . .
C15 C -0.0019(3) -0.7105(13) 0.2043(3) 0.0689(15) Uani 1 1 d . . . . .
C5 C 0.3123(3) 0.9526(14) 0.0371(3) 0.0751(17) Uani 1 1 d . . . . .
O1 O 0.3569(2) 1.0860(10) 0.0861(2) 0.0821(12) Uani 1 1 d . . . . .
C16 C 0.0496(3) -0.5428(15) 0.2473(3) 0.0763(17) Uani 1 1 d . . . . .
H16 H 0.0603 -0.5552 0.2891 0.092 Uiso 1 1 calc R . . . .
O4 O -0.0848(3) -1.0254(12) 0.1870(2) 0.0970(15) Uani 1 1 d . . . . .
C8 C 0.1824(3) 0.4351(15) 0.0155(3) 0.0779(18) Uani 1 1 d . . . . .
H8 H 0.1482 0.3501 -0.0173 0.093 Uiso 1 1 calc R . . . .
O2 O 0.3053(3) 0.9809(13) -0.0143(2) 0.1048(17) Uani 1 1 d . . . . .
C6 C 0.2731(3) 0.7573(12) 0.0545(3) 0.0638(14) Uani 1 1 d . . . . .
C18 C -0.0359(4) -0.8882(16) 0.2302(3) 0.0818(18) Uani 1 1 d . . . . .
O3 O -0.0216(3) -0.9038(15) 0.2837(3) 0.123(2) Uani 1 1 d . . . . .
C7 C 0.2200(3) 0.6230(16) 0.0051(3) 0.0807(18) Uani 1 1 d . . . . .
H7 H 0.2109 0.6657 -0.0353 0.097 Uiso 1 1 calc R . . . .
C3 C 0.4574(4) 1.0984(16) 0.0846(4) 0.088(2) Uani 1 1 d . . . . .
H3A H 0.4440 0.9497 0.0536 0.105 Uiso 1 1 calc R . . . .
H3B H 0.4752 1.0067 0.1247 0.105 Uiso 1 1 calc R . . . .
C4 C 0.4015(4) 1.2645(15) 0.0764(4) 0.091(2) Uani 1 1 d . . . . .
H4A H 0.4147 1.4218 0.1054 0.109 Uiso 1 1 calc R . . . .
H4B H 0.3811 1.3430 0.0350 0.109 Uiso 1 1 calc R . . . .
C2 C 0.5091(4) 1.2749(18) 0.0801(4) 0.102(3) Uani 1 1 d . . . . .
H2A H 0.4920 1.3557 0.0390 0.122 Uiso 1 1 calc R . . . .
H2B H 0.5201 1.4319 0.1091 0.122 Uiso 1 1 calc R . . . .
C20 C -0.1802(5) -1.268(3) 0.1596(5) 0.148(5) Uani 1 1 d . . . . .
H20A H -0.1715 -1.3824 0.1311 0.177 Uiso 1 1 calc R . . . .
H20B H -0.2026 -1.0989 0.1377 0.177 Uiso 1 1 calc R . . . .
C19 C -0.1230(5) -1.186(2) 0.2081(5) 0.121(3) Uani 1 1 d . . . . .
H19A H -0.0997 -1.3546 0.2298 0.146 Uiso 1 1 calc R . . . .
H19B H -0.1311 -1.0716 0.2368 0.146 Uiso 1 1 calc R . . . .
N1 N 0.2596(2) 0.4394(11) 0.18381(19) 0.0663(12) Uani 1 1 d . . . . .
C1 C 0.5678(5) 1.116(3) 0.0927(6) 0.146(4) Uani 1 1 d . . . . .
H1A H 0.5570 0.9429 0.0691 0.219 Uiso 1 1 calc GR . . . .
H1B H 0.5903 1.0713 0.1358 0.219 Uiso 1 1 calc GR . . . .
H1C H 0.5942 1.2310 0.0812 0.219 Uiso 1 1 calc GR . . . .
C22 C -0.2884(6) -1.324(4) 0.1566(9) 0.256(11) Uani 1 1 d D . . . .
H22A H -0.2992 -1.1959 0.1227 0.384 Uiso 1 1 calc GR . . . .
H22B H -0.2908 -1.2260 0.1900 0.384 Uiso 1 1 calc GR . . . .
H22C H -0.3176 -1.4814 0.1437 0.384 Uiso 1 1 calc GR . . . .
C21 C -0.2225(6) -1.434(3) 0.1776(7) 0.191(7) Uani 1 1 d D . . . .
H21A H -0.2022 -1.4459 0.2223 0.229 Uiso 1 1 calc R . . . .
H21B H -0.2255 -1.6262 0.1620 0.229 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 N2 1.799(4) . ?
Se1 N1 1.763(5) . ?
Se2 N4 1.781(5) . ?
Se2 N3 1.781(5) . ?
C10 C11 1.428(8) . ?
C10 C9 1.433(7) . ?
C10 N1 1.329(7) . ?
N4 C13 1.333(7) . ?
N3 C12 1.275(7) . ?
N2 C9 1.352(7) . ?
C12 C13 1.433(7) . ?
C12 C17 1.419(8) . ?
C14 C13 1.423(8) . ?
C14 C15 1.366(8) . ?
C11 C6 1.341(8) . ?
C17 C16 1.342(9) . ?
C9 C8 1.450(8) . ?
C15 C16 1.428(9) . ?
C15 C18 1.485(9) . ?
C5 O1 1.334(8) . ?
C5 O2 1.194(8) . ?
C5 C6 1.499(9) . ?
O1 C4 1.452(8) . ?
O4 C18 1.323(9) . ?
O4 C19 1.442(9) . ?
C8 C7 1.357(9) . ?
C6 C7 1.430(9) . ?
C18 O3 1.191(8) . ?
C3 C4 1.470(10) . ?
C3 C2 1.525(10) . ?
C2 C1 1.483(13) . ?
C20 C19 1.385(13) . ?
C20 C21 1.486(13) . ?
C22 C21 1.496(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
N1 Se1 N2 95.33(19) . . ?
N4 Se2 N3 91.4(2) . . ?
C11 C10 C9 120.6(5) . . ?
N1 C10 C11 124.6(5) . . ?
N1 C10 C9 114.8(5) . . ?
C13 N4 Se2 107.3(4) . . ?
C12 N3 Se2 110.6(4) . . ?
C9 N2 Se1 103.8(3) . . ?
N3 C12 C13 114.5(5) . . ?
N3 C12 C17 125.3(5) . . ?
C17 C12 C13 120.2(5) . . ?
C15 C14 C13 118.7(6) . . ?
N4 C13 C12 116.1(5) . . ?
N4 C13 C14 124.4(5) . . ?
C14 C13 C12 119.4(5) . . ?
C6 C11 C10 119.5(5) . . ?
C16 C17 C12 118.6(6) . . ?
C10 C9 C8 117.9(5) . . ?
N2 C9 C10 118.4(5) . . ?
N2 C9 C8 123.7(5) . . ?
C14 C15 C16 120.9(6) . . ?
C14 C15 C18 122.7(6) . . ?
C16 C15 C18 116.4(6) . . ?
O1 C5 C6 112.0(5) . . ?
O2 C5 O1 124.1(6) . . ?
O2 C5 C6 123.9(7) . . ?
C5 O1 C4 117.5(6) . . ?
C17 C16 C15 122.3(6) . . ?
C18 O4 C19 115.9(7) . . ?
C7 C8 C9 119.0(6) . . ?
C11 C6 C5 122.0(6) . . ?
C11 C6 C7 121.0(6) . . ?
C7 C6 C5 117.0(6) . . ?
O4 C18 C15 112.6(6) . . ?
O3 C18 C15 124.3(8) . . ?
O3 C18 O4 123.2(7) . . ?
C8 C7 C6 122.0(6) . . ?
C4 C3 C2 114.0(6) . . ?
O1 C4 C3 110.5(5) . . ?
C1 C2 C3 115.0(8) . . ?
C19 C20 C21 115.1(10) . . ?
C20 C19 O4 111.8(8) . . ?
C10 N1 Se1 107.7(4) . . ?
C20 C21 C22 117.5(11) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
