# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_[Se(IAd)]
_database_code_depnum_ccdc_archive 'CCDC 1024807'
_audit_update_record             
;
2014-09-17 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C23 H32 N2 Se'
_chemical_formula_moiety         'C23 H32 N2 Se'
_chemical_formula_weight         415.48
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_space_group_IT_number           33
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2+Z
3 1/2+X,1/2-Y,+Z
4 -X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   23.300(2)
_cell_length_b                   7.0807(7)
_cell_length_c                   11.6415(13)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1920.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6161
_cell_measurement_theta_min      1.75
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872.00
_exptl_absorpt_coefficient_mu    1.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_T_max  0.906

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            22163
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_theta_max         25.381
_diffrn_reflns_theta_min         1.748
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3522
_reflns_number_gt                3326
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0568
_refine_ls_wR_factor_gt          0.0562
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3522
_refine_ls_number_parameters     235
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0357P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.05
_refine_diff_density_min         -0.15
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1490 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.007(4)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.38477(2) 0.60157(4) 0.50692(4) 0.02580(10) Uani 1 4 d . . .
N2 N 0.35425(11) 0.3764(3) 0.7066(2) 0.0231(6) Uani 1 4 d . . .
N5 N 0.42702(11) 0.5644(3) 0.7404(2) 0.0217(5) Uani 1 4 d . . .
C1 C 0.38836(11) 0.5125(4) 0.6576(3) 0.0212(6) Uani 1 4 d . . .
C3 C 0.37272(14) 0.3447(5) 0.8172(3) 0.0278(7) Uani 1 4 d . . .
C4 C 0.41703(14) 0.4585(5) 0.8382(3) 0.0265(7) Uani 1 4 d . . .
C6 C 0.30277(12) 0.2789(4) 0.6547(3) 0.0232(7) Uani 1 4 d . . .
C7 C 0.32069(12) 0.1639(5) 0.5496(3) 0.0265(7) Uani 1 4 d . . .
C8 C 0.26781(13) 0.0682(4) 0.4969(5) 0.0350(8) Uani 1 4 d . . .
C9 C 0.24192(15) -0.0668(5) 0.5849(4) 0.0375(9) Uani 1 4 d . . .
C10 C 0.22370(14) 0.0452(5) 0.6909(3) 0.0341(8) Uani 1 4 d . . .
C11 C 0.27633(14) 0.1434(5) 0.7432(3) 0.0312(8) Uani 1 4 d . . .
C12 C 0.25725(14) 0.4268(4) 0.6227(3) 0.0290(8) Uani 1 4 d . . .
C13 C 0.20516(14) 0.3283(5) 0.5702(4) 0.0388(9) Uani 1 4 d . . .
C14 C 0.22386(15) 0.2197(6) 0.4635(3) 0.0403(9) Uani 1 4 d . . .
C15 C 0.17889(14) 0.1933(5) 0.6580(4) 0.0410(9) Uani 1 4 d . . .
C16 C 0.47499(12) 0.7064(4) 0.7318(3) 0.0201(6) Uani 1 4 d . . .
C17 C 0.52105(13) 0.6303(4) 0.6494(3) 0.0242(7) Uani 1 4 d . . .
C18 C 0.57051(13) 0.7738(5) 0.6416(3) 0.0271(7) Uani 1 4 d . . .
C19 C 0.59723(14) 0.8019(5) 0.7601(3) 0.0302(8) Uani 1 4 d . . .
C20 C 0.55171(14) 0.8790(4) 0.8424(3) 0.0267(7) Uani 1 4 d . . .
C21 C 0.50243(13) 0.7349(4) 0.8505(3) 0.0234(6) Uani 1 4 d . . .
C22 C 0.45224(15) 0.8988(4) 0.6914(3) 0.0242(8) Uani 1 4 d . . .
C23 C 0.50215(14) 1.0390(4) 0.6803(3) 0.0272(7) Uani 1 4 d . . .
C24 C 0.54676(14) 0.9618(5) 0.5965(3) 0.0294(7) Uani 1 4 d . . .
C25 C 0.52986(16) 1.0692(5) 0.7982(3) 0.0290(8) Uani 1 4 d . . .
H3 H 0.35662 0.25666 0.86966 0.0334 Uiso 1 4 calc R . .
H4 H 0.43804 0.46565 0.90804 0.0318 Uiso 1 4 calc R . .
H7A H 0.34911 0.06698 0.57235 0.0317 Uiso 1 4 calc R . .
H7B H 0.3388 0.24793 0.49206 0.0317 Uiso 1 4 calc R . .
H8 H 0.27949 -0.00421 0.42697 0.0420 Uiso 1 4 calc R . .
H9A H 0.27056 -0.16361 0.60668 0.0450 Uiso 1 4 calc R . .
H9B H 0.20824 -0.1317 0.5513 0.0450 Uiso 1 4 calc R . .
H10 H 0.20683 -0.04314 0.74879 0.0409 Uiso 1 4 calc R . .
H11A H 0.30509 0.04765 0.76621 0.0374 Uiso 1 4 calc R . .
H11B H 0.26479 0.21471 0.8126 0.0374 Uiso 1 4 calc R . .
H12A H 0.2455 0.4975 0.6922 0.0347 Uiso 1 4 calc R . .
H12B H 0.27351 0.51771 0.56692 0.0347 Uiso 1 4 calc R . .
H13 H 0.176 0.42526 0.54801 0.0466 Uiso 1 4 calc R . .
H14A H 0.24111 0.30776 0.40718 0.0484 Uiso 1 4 calc R . .
H14B H 0.19007 0.15938 0.42723 0.0484 Uiso 1 4 calc R . .
H15A H 0.1447 0.13086 0.62481 0.0492 Uiso 1 4 calc R . .
H15B H 0.16674 0.26438 0.72712 0.0492 Uiso 1 4 calc R . .
H17A H 0.50419 0.60997 0.57234 0.0291 Uiso 1 4 calc R . .
H17B H 0.53574 0.5078 0.67794 0.0291 Uiso 1 4 calc R . .
H18 H 0.60035 0.72547 0.58732 0.0326 Uiso 1 4 calc R . .
H19A H 0.6297 0.89166 0.75489 0.0363 Uiso 1 4 calc R . .
H19B H 0.6121 0.68 0.78931 0.0363 Uiso 1 4 calc R . .
H20 H 0.56911 0.89661 0.92014 0.0321 Uiso 1 4 calc R . .
H21A H 0.5174 0.61294 0.87922 0.0281 Uiso 1 4 calc R . .
H21B H 0.47312 0.78089 0.9053 0.0281 Uiso 1 4 calc R . .
H22A H 0.43283 0.88452 0.61629 0.0291 Uiso 1 4 calc R . .
H22B H 0.42387 0.94733 0.74744 0.0291 Uiso 1 4 calc R . .
H23 H 0.48725 1.1623 0.65089 0.0327 Uiso 1 4 calc R . .
H24A H 0.57844 1.05385 0.58784 0.0353 Uiso 1 4 calc R . .
H24B H 0.52895 0.94233 0.52024 0.0353 Uiso 1 4 calc R . .
H25A H 0.56213 1.15949 0.79172 0.0349 Uiso 1 4 calc R . .
H25B H 0.50134 1.12196 0.85248 0.0349 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Se1 C1 1.866(3) yes . .
N2 C1 1.373(4) yes . .
N2 C3 1.376(4) yes . .
N2 C6 1.510(4) yes . .
N5 C1 1.370(4) yes . .
N5 C4 1.383(4) yes . .
N5 C16 1.507(4) yes . .
C3 C4 1.332(5) yes . .
C6 C7 1.528(5) yes . .
C6 C11 1.537(5) yes . .
C6 C12 1.536(4) yes . .
C7 C8 1.534(5) yes . .
C8 C9 1.525(6) yes . .
C8 C14 1.533(5) yes . .
C9 C10 1.527(6) yes . .
C10 C11 1.536(5) yes . .
C10 C15 1.529(5) yes . .
C12 C13 1.527(5) yes . .
C13 C14 1.525(6) yes . .
C13 C15 1.527(6) yes . .
C16 C17 1.536(4) yes . .
C16 C21 1.536(4) yes . .
C16 C22 1.535(4) yes . .
C17 C18 1.539(4) yes . .
C18 C19 1.527(5) yes . .
C18 C24 1.534(5) yes . .
C19 C20 1.529(5) yes . .
C20 C21 1.539(4) yes . .
C20 C25 1.528(5) yes . .
C22 C23 1.534(5) yes . .
C23 C24 1.526(5) yes . .
C23 C25 1.533(5) yes . .
C3 H3 0.950 no . .
C4 H4 0.950 no . .
C7 H7A 0.990 no . .
C7 H7B 0.990 no . .
C8 H8 1.000 no . .
C9 H9A 0.990 no . .
C9 H9B 0.990 no . .
C10 H10 1.000 no . .
C11 H11A 0.990 no . .
C11 H11B 0.990 no . .
C12 H12A 0.990 no . .
C12 H12B 0.990 no . .
C13 H13 1.000 no . .
C14 H14A 0.990 no . .
C14 H14B 0.990 no . .
C15 H15A 0.990 no . .
C15 H15B 0.990 no . .
C17 H17A 0.990 no . .
C17 H17B 0.990 no . .
C18 H18 1.000 no . .
C19 H19A 0.990 no . .
C19 H19B 0.990 no . .
C20 H20 1.000 no . .
C21 H21A 0.990 no . .
C21 H21B 0.990 no . .
C22 H22A 0.990 no . .
C22 H22B 0.990 no . .
C23 H23 1.000 no . .
C24 H24A 0.990 no . .
C24 H24B 0.990 no . .
C25 H25A 0.990 no . .
C25 H25B 0.990 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N2 C3 108.8(3) yes . . .
C1 N2 C6 127.9(3) yes . . .
C3 N2 C6 123.3(3) yes . . .
C1 N5 C4 108.9(3) yes . . .
C1 N5 C16 128.3(3) yes . . .
C4 N5 C16 122.8(3) yes . . .
Se1 C1 N2 127.0(2) yes . . .
Se1 C1 N5 126.9(2) yes . . .
N2 C1 N5 106.0(3) yes . . .
N2 C3 C4 108.4(3) yes . . .
N5 C4 C3 107.9(3) yes . . .
N2 C6 C7 110.3(2) yes . . .
N2 C6 C11 109.6(3) yes . . .
N2 C6 C12 109.5(2) yes . . .
C7 C6 C11 108.3(3) yes . . .
C7 C6 C12 111.0(3) yes . . .
C11 C6 C12 108.1(2) yes . . .
C6 C7 C8 109.6(3) yes . . .
C7 C8 C9 109.1(4) yes . . .
C7 C8 C14 109.2(3) yes . . .
C9 C8 C14 110.2(3) yes . . .
C8 C9 C10 109.1(3) yes . . .
C9 C10 C11 109.5(3) yes . . .
C9 C10 C15 110.1(3) yes . . .
C11 C10 C15 109.5(3) yes . . .
C6 C11 C10 109.7(3) yes . . .
C6 C12 C13 109.5(3) yes . . .
C12 C13 C14 109.2(3) yes . . .
C12 C13 C15 109.6(3) yes . . .
C14 C13 C15 110.1(3) yes . . .
C8 C14 C13 109.7(3) yes . . .
C10 C15 C13 108.9(3) yes . . .
N5 C16 C17 109.0(2) yes . . .
N5 C16 C21 109.6(2) yes . . .
N5 C16 C22 110.9(2) yes . . .
C17 C16 C21 108.5(2) yes . . .
C17 C16 C22 111.2(3) yes . . .
C21 C16 C22 107.6(2) yes . . .
C16 C17 C18 109.2(2) yes . . .
C17 C18 C19 109.7(3) yes . . .
C17 C18 C24 108.8(2) yes . . .
C19 C18 C24 110.1(3) yes . . .
C18 C19 C20 109.2(3) yes . . .
C19 C20 C21 108.6(3) yes . . .
C19 C20 C25 109.6(3) yes . . .
C21 C20 C25 110.9(3) yes . . .
C16 C21 C20 110.0(3) yes . . .
C16 C22 C23 109.8(3) yes . . .
C22 C23 C24 109.8(3) yes . . .
C22 C23 C25 109.5(3) yes . . .
C24 C23 C25 109.6(3) yes . . .
C18 C24 C23 109.8(3) yes . . .
C20 C25 C23 108.6(3) yes . . .
N2 C3 H3 125.804 no . . .
C4 C3 H3 125.784 no . . .
N5 C4 H4 126.061 no . . .
C3 C4 H4 126.069 no . . .
C6 C7 H7A 109.742 no . . .
C6 C7 H7B 109.745 no . . .
C8 C7 H7A 109.745 no . . .
C8 C7 H7B 109.739 no . . .
H7A C7 H7B 108.220 no . . .
C7 C8 H8 109.467 no . . .
C9 C8 H8 109.473 no . . .
C14 C8 H8 109.476 no . . .
C8 C9 H9A 109.855 no . . .
C8 C9 H9B 109.864 no . . .
C10 C9 H9A 109.851 no . . .
C10 C9 H9B 109.861 no . . .
H9A C9 H9B 108.286 no . . .
C9 C10 H10 109.239 no . . .
C11 C10 H10 109.248 no . . .
C15 C10 H10 109.233 no . . .
C6 C11 H11A 109.729 no . . .
C6 C11 H11B 109.732 no . . .
C10 C11 H11A 109.739 no . . .
C10 C11 H11B 109.741 no . . .
H11A C11 H11B 108.197 no . . .
C6 C12 H12A 109.752 no . . .
C6 C12 H12B 109.754 no . . .
C13 C12 H12A 109.773 no . . .
C13 C12 H12B 109.771 no . . .
H12A C12 H12B 108.227 no . . .
C12 C13 H13 109.266 no . . .
C14 C13 H13 109.276 no . . .
C15 C13 H13 109.276 no . . .
C8 C14 H14A 109.742 no . . .
C8 C14 H14B 109.731 no . . .
C13 C14 H14A 109.732 no . . .
C13 C14 H14B 109.725 no . . .
H14A C14 H14B 108.210 no . . .
C10 C15 H15A 109.915 no . . .
C10 C15 H15B 109.912 no . . .
C13 C15 H15A 109.918 no . . .
C13 C15 H15B 109.918 no . . .
H15A C15 H15B 108.318 no . . .
C16 C17 H17A 109.833 no . . .
C16 C17 H17B 109.842 no . . .
C18 C17 H17A 109.855 no . . .
C18 C17 H17B 109.849 no . . .
H17A C17 H17B 108.277 no . . .
C17 C18 H18 109.382 no . . .
C19 C18 H18 109.396 no . . .
C24 C18 H18 109.392 no . . .
C18 C19 H19A 109.831 no . . .
C18 C19 H19B 109.838 no . . .
C20 C19 H19A 109.830 no . . .
C20 C19 H19B 109.838 no . . .
H19A C19 H19B 108.268 no . . .
C19 C20 H20 109.269 no . . .
C21 C20 H20 109.244 no . . .
C25 C20 H20 109.247 no . . .
C16 C21 H21A 109.654 no . . .
C16 C21 H21B 109.656 no . . .
C20 C21 H21A 109.653 no . . .
C20 C21 H21B 109.652 no . . .
H21A C21 H21B 108.161 no . . .
C16 C22 H22A 109.712 no . . .
C16 C22 H22B 109.713 no . . .
C23 C22 H22A 109.711 no . . .
C23 C22 H22B 109.712 no . . .
H22A C22 H22B 108.200 no . . .
C22 C23 H23 109.316 no . . .
C24 C23 H23 109.322 no . . .
C25 C23 H23 109.317 no . . .
C18 C24 H24A 109.714 no . . .
C18 C24 H24B 109.715 no . . .
C23 C24 H24A 109.711 no . . .
C23 C24 H24B 109.714 no . . .
H24A C24 H24B 108.200 no . . .
C20 C25 H25A 109.984 no . . .
C20 C25 H25B 109.982 no . . .
C23 C25 H25A 109.971 no . . .
C23 C25 H25B 109.972 no . . .
H25A C25 H25B 108.355 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N2 C3 C4 0.5(3) no . . . .
C3 N2 C1 Se1 176.8(2) no . . . .
C3 N2 C1 N5 -0.9(3) no . . . .
C1 N2 C6 C7 63.5(3) no . . . .
C1 N2 C6 C11 -177.4(2) no . . . .
C1 N2 C6 C12 -58.9(4) no . . . .
C6 N2 C1 Se1 -5.8(4) no . . . .
C6 N2 C1 N5 176.4(2) no . . . .
C3 N2 C6 C7 -119.5(3) no . . . .
C3 N2 C6 C11 -0.4(4) no . . . .
C3 N2 C6 C12 118.0(3) no . . . .
C6 N2 C3 C4 -177.0(2) no . . . .
C1 N5 C4 C3 -0.7(3) no . . . .
C4 N5 C1 Se1 -176.8(2) no . . . .
C4 N5 C1 N2 1.0(3) no . . . .
C1 N5 C16 C17 -68.2(3) no . . . .
C1 N5 C16 C21 173.2(2) no . . . .
C1 N5 C16 C22 54.6(4) no . . . .
C16 N5 C1 Se1 1.1(4) no . . . .
C16 N5 C1 N2 178.8(2) no . . . .
C4 N5 C16 C17 109.4(3) no . . . .
C4 N5 C16 C21 -9.2(3) no . . . .
C4 N5 C16 C22 -127.8(3) no . . . .
C16 N5 C4 C3 -178.7(2) no . . . .
N2 C3 C4 N5 0.1(4) no . . . .
N2 C6 C7 C8 -179.2(2) no . . . .
N2 C6 C11 C10 179.6(2) no . . . .
N2 C6 C12 C13 -180.0(2) no . . . .
C7 C6 C11 C10 -60.0(3) no . . . .
C11 C6 C7 C8 60.9(3) no . . . .
C7 C6 C12 C13 58.0(3) no . . . .
C12 C6 C7 C8 -57.7(3) no . . . .
C11 C6 C12 C13 -60.6(3) no . . . .
C12 C6 C11 C10 60.3(3) no . . . .
C6 C7 C8 C9 -61.7(3) no . . . .
C6 C7 C8 C14 58.7(4) no . . . .
C7 C8 C9 C10 60.8(3) no . . . .
C7 C8 C14 C13 -61.1(4) no . . . .
C9 C8 C14 C13 58.6(4) no . . . .
C14 C8 C9 C10 -59.0(4) no . . . .
C8 C9 C10 C11 -60.2(3) no . . . .
C8 C9 C10 C15 60.2(3) no . . . .
C9 C10 C11 C6 60.2(3) no . . . .
C9 C10 C15 C13 -60.4(3) no . . . .
C11 C10 C15 C13 60.0(4) no . . . .
C15 C10 C11 C6 -60.7(4) no . . . .
C6 C12 C13 C14 -59.3(4) no . . . .
C6 C12 C13 C15 61.5(3) no . . . .
C12 C13 C14 C8 61.5(4) no . . . .
C12 C13 C15 C10 -60.6(4) no . . . .
C14 C13 C15 C10 59.7(4) no . . . .
C15 C13 C14 C8 -58.9(3) no . . . .
N5 C16 C17 C18 -179.2(2) no . . . .
N5 C16 C21 C20 179.70(19) no . . . .
N5 C16 C22 C23 -178.5(2) no . . . .
C17 C16 C21 C20 60.8(3) no . . . .
C21 C16 C17 C18 -59.9(3) no . . . .
C17 C16 C22 C23 -57.0(3) no . . . .
C22 C16 C17 C18 58.2(3) no . . . .
C21 C16 C22 C23 61.6(3) no . . . .
C22 C16 C21 C20 -59.6(3) no . . . .
C16 C17 C18 C19 60.7(3) no . . . .
C16 C17 C18 C24 -59.9(3) no . . . .
C17 C18 C19 C20 -60.9(3) no . . . .
C17 C18 C24 C23 61.8(3) no . . . .
C19 C18 C24 C23 -58.5(3) no . . . .
C24 C18 C19 C20 58.8(3) no . . . .
C18 C19 C20 C21 60.5(3) no . . . .
C18 C19 C20 C25 -60.7(3) no . . . .
C19 C20 C21 C16 -61.1(3) no . . . .
C19 C20 C25 C23 61.6(3) no . . . .
C21 C20 C25 C23 -58.3(3) no . . . .
C25 C20 C21 C16 59.4(3) no . . . .
C16 C22 C23 C24 57.8(3) no . . . .
C16 C22 C23 C25 -62.6(3) no . . . .
C22 C23 C24 C18 -60.8(3) no . . . .
C22 C23 C25 C20 59.6(3) no . . . .
C24 C23 C25 C20 -60.9(3) no . . . .
C25 C23 C24 C18 59.4(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Se1 C6 3.439(3) no . .
Se1 C7 3.475(3) no . .
Se1 C12 3.490(3) no . .
Se1 C16 3.438(3) no . .
Se1 C17 3.588(3) no . .
Se1 C22 3.393(3) no . .
C1 C7 3.187(4) no . .
C1 C12 3.141(4) no . .
C1 C17 3.204(4) no . .
C1 C22 3.139(4) no . .
C3 C7 3.580(5) no . .
C3 C11 2.796(5) no . .
C3 C12 3.564(5) no . .
C4 C17 3.491(5) no . .
C4 C21 2.795(5) no . .
C6 C9 2.943(5) no . .
C6 C14 2.917(5) no . .
C6 C15 2.950(4) no . .
C7 C10 2.919(5) no . .
C7 C13 2.943(4) no . .
C7 C15 3.543(5) no . .
C8 C11 2.923(7) no . .
C8 C12 2.941(5) no . .
C8 C15 2.932(6) no . .
C9 C12 3.540(5) no . .
C9 C13 2.930(5) no . .
C10 C12 2.922(5) no . .
C10 C14 2.922(5) no . .
C11 C13 2.919(5) no . .
C11 C14 3.520(5) no . .
C16 C19 2.946(4) no . .
C16 C24 2.923(4) no . .
C16 C25 2.972(4) no . .
C17 C20 2.942(5) no . .
C17 C23 2.949(4) no . .
C17 C25 3.564(5) no . .
C18 C21 2.916(4) no . .
C18 C22 2.952(5) no . .
C18 C25 2.932(5) no . .
C19 C22 3.539(5) no . .
C19 C23 2.931(5) no . .
C20 C22 2.912(5) no . .
C20 C24 2.923(5) no . .
C21 C23 2.926(5) no . .
C21 C24 3.519(5) no . .
Se1 H7B 2.7290 no . .
Se1 H12B 2.7497 no . .
Se1 H17A 2.8855 no . .
Se1 H22A 2.6247 no . .
N2 H4 3.1158 no . .
N2 H7A 2.6941 no . .
N2 H7B 2.6827 no . .
N2 H11A 2.6855 no . .
N2 H11B 2.6791 no . .
N2 H12A 2.6803 no . .
N2 H12B 2.6806 no . .
N5 H3 3.1148 no . .
N5 H17A 2.6770 no . .
N5 H17B 2.6659 no . .
N5 H21A 2.6765 no . .
N5 H21B 2.6810 no . .
N5 H22A 2.6917 no . .
N5 H22B 2.7137 no . .
C1 H3 3.1500 no . .
C1 H4 3.1544 no . .
C1 H7A 3.4310 no . .
C1 H7B 2.9251 no . .
C1 H12A 3.3546 no . .
C1 H12B 2.8769 no . .
C1 H17A 2.9573 no . .
C1 H17B 3.4423 no . .
C1 H22A 2.8713 no . .
C1 H22B 3.3554 no . .
C3 H7A 3.5065 no . .
C3 H11A 2.6945 no . .
C3 H11B 2.6785 no . .
C3 H12A 3.4748 no . .
C4 H17B 3.3548 no . .
C4 H21A 2.6254 no . .
C4 H21B 2.7437 no . .
C6 H3 2.8041 no . .
C6 H8 3.3674 no . .
C6 H9A 3.2701 no . .
C6 H10 3.3760 no . .
C6 H13 3.3675 no . .
C6 H14A 3.2260 no . .
C6 H15B 3.2814 no . .
C7 H9A 2.6804 no . .
C7 H9B 3.3536 no . .
C7 H11A 2.6778 no . .
C7 H11B 3.3469 no . .
C7 H12A 3.3772 no . .
C7 H12B 2.7431 no . .
C7 H14A 2.6876 no . .
C7 H14B 3.3604 no . .
C8 H10 3.3521 no . .
C8 H11A 3.2562 no . .
C8 H12B 3.2884 no . .
C8 H13 3.3649 no . .
C8 H15A 3.2621 no . .
C9 H7A 2.6750 no . .
C9 H7B 3.3507 no . .
C9 H11A 2.6981 no . .
C9 H11B 3.3593 no . .
C9 H14A 3.3632 no . .
C9 H14B 2.7186 no . .
C9 H15A 2.7029 no . .
C9 H15B 3.3628 no . .
C10 H7A 3.2352 no . .
C10 H8 3.3543 no . .
C10 H12A 3.2427 no . .
C10 H13 3.3532 no . .
C10 H14B 3.2693 no . .
C11 H3 2.5120 no . .
C11 H7A 2.6691 no . .
C11 H7B 3.3488 no . .
C11 H9A 2.6962 no . .
C11 H9B 3.3618 no . .
C11 H12A 2.6749 no . .
C11 H12B 3.3527 no . .
C11 H15A 3.3636 no . .
C11 H15B 2.6998 no . .
C12 H7A 3.3786 no . .
C12 H7B 2.7436 no . .
C12 H11A 3.3524 no . .
C12 H11B 2.6780 no . .
C12 H14A 2.6735 no . .
C12 H14B 3.3487 no . .
C12 H15A 3.3567 no . .
C12 H15B 2.6919 no . .
C13 H7B 3.2935 no . .
C13 H8 3.3649 no . .
C13 H9B 3.2653 no . .
C13 H10 3.3529 no . .
C13 H11B 3.2467 no . .
C14 H7A 3.3604 no . .
C14 H7B 2.7061 no . .
C14 H9A 3.3659 no . .
C14 H9B 2.7144 no . .
C14 H12A 3.3488 no . .
C14 H12B 2.6911 no . .
C14 H15A 2.7065 no . .
C14 H15B 3.3604 no . .
C15 H9A 3.3627 no . .
C15 H9B 2.7034 no . .
C15 H11A 3.3611 no . .
C15 H11B 2.6958 no . .
C15 H12A 2.6842 no . .
C15 H12B 3.3556 no . .
C15 H14A 3.3594 no . .
C15 H14B 2.7100 no . .
C16 H4 2.8034 no . .
C16 H18 3.3730 no . .
C16 H19B 3.2695 no . .
C16 H20 3.3813 no . .
C16 H23 3.3746 no . .
C16 H24B 3.2302 no . .
C16 H25B 3.3181 no . .
C17 H19A 3.3676 no . .
C17 H19B 2.6976 no . .
C17 H21A 2.6795 no . .
C17 H21B 3.3553 no . .
C17 H22A 2.7592 no . .
C17 H22B 3.3864 no . .
C17 H24A 3.3608 no . .
C17 H24B 2.6787 no . .
C18 H20 3.3574 no . .
C18 H21A 3.2376 no . .
C18 H22A 3.3154 no . .
C18 H23 3.3676 no . .
C18 H25A 3.2480 no . .
C19 H17A 3.3654 no . .
C19 H17B 2.7027 no . .
C19 H21A 2.6779 no . .
C19 H21B 3.3526 no . .
C19 H24A 2.7200 no . .
C19 H24B 3.3645 no . .
C19 H25A 2.6862 no . .
C19 H25B 3.3592 no . .
C20 H17B 3.2727 no . .
C20 H18 3.3587 no . .
C20 H22B 3.2136 no . .
C20 H23 3.3537 no . .
C20 H24A 3.2709 no . .
C21 H4 2.5171 no . .
C21 H17A 3.3566 no . .
C21 H17B 2.6874 no . .
C21 H19A 3.3560 no . .
C21 H19B 2.6810 no . .
C21 H22A 3.3441 no . .
C21 H22B 2.6553 no . .
C21 H25A 3.3822 no . .
C21 H25B 2.7407 no . .
C22 H17A 2.7513 no . .
C22 H17B 3.3874 no . .
C22 H21A 3.3437 no . .
C22 H21B 2.6706 no . .
C22 H24A 3.3625 no . .
C22 H24B 2.6948 no . .
C22 H25A 3.3654 no . .
C22 H25B 2.7056 no . .
C23 H17A 3.2876 no . .
C23 H18 3.3666 no . .
C23 H19A 3.2673 no . .
C23 H20 3.3539 no . .
C23 H21B 3.2650 no . .
C24 H17A 2.6960 no . .
C24 H17B 3.3611 no . .
C24 H19A 2.7165 no . .
C24 H19B 3.3667 no . .
C24 H22A 2.7201 no . .
C24 H22B 3.3608 no . .
C24 H25A 2.6927 no . .
C24 H25B 3.3592 no . .
C25 H19A 2.6919 no . .
C25 H19B 3.3581 no . .
C25 H21A 3.3778 no . .
C25 H21B 2.7329 no . .
C25 H22A 3.3626 no . .
C25 H22B 2.6820 no . .
C25 H24A 2.7003 no . .
C25 H24B 3.3586 no . .
H3 H4 2.4471 no . .
H3 H11A 2.2544 no . .
H3 H11B 2.2600 no . .
H4 H17B 3.5280 no . .
H4 H21A 2.1493 no . .
H4 H21B 2.3773 no . .
H7A H8 2.3979 no . .
H7A H9A 2.4850 no . .
H7A H9B 3.5795 no . .
H7A H11A 2.4827 no . .
H7A H11B 3.5744 no . .
H7A H14A 3.5967 no . .
H7B H8 2.3814 no . .
H7B H9A 3.5777 no . .
H7B H11A 3.5796 no . .
H7B H12B 2.5928 no . .
H7B H14A 2.5173 no . .
H8 H9A 2.3862 no . .
H8 H9B 2.3803 no . .
H8 H14A 2.3942 no . .
H8 H14B 2.3838 no . .
H9A H10 2.3811 no . .
H9A H11A 2.5167 no . .
H9A H11B 3.5973 no . .
H9B H10 2.3833 no . .
H9B H14B 2.5521 no . .
H9B H15A 2.5260 no . .
H10 H11A 2.3866 no . .
H10 H11B 2.3893 no . .
H10 H15A 2.3868 no . .
H10 H15B 2.3828 no . .
H11A H12A 3.5799 no . .
H11A H15B 3.5991 no . .
H11B H12A 2.4852 no . .
H11B H12B 3.5811 no . .
H11B H15B 2.5166 no . .
H12A H13 2.3878 no . .
H12A H14A 3.5812 no . .
H12A H15A 3.5876 no . .
H12A H15B 2.5015 no . .
H12B H13 2.3746 no . .
H12B H14A 2.4976 no . .
H12B H14B 3.5863 no . .
H12B H15B 3.5895 no . .
H13 H14A 2.3836 no . .
H13 H14B 2.3725 no . .
H13 H15A 2.3826 no . .
H13 H15B 2.3858 no . .
H14B H15A 2.5395 no . .
H17A H18 2.3915 no . .
H17A H19B 3.5983 no . .
H17A H21A 3.5858 no . .
H17A H22A 2.6087 no . .
H17A H24A 3.5922 no . .
H17A H24B 2.4978 no . .
H17B H18 2.3989 no . .
H17B H19B 2.5166 no . .
H17B H21A 2.4955 no . .
H17B H21B 3.5880 no . .
H17B H24B 3.5864 no . .
H18 H19A 2.3786 no . .
H18 H19B 2.3891 no . .
H18 H24A 2.3806 no . .
H18 H24B 2.3948 no . .
H19A H20 2.3864 no . .
H19A H21A 3.5828 no . .
H19A H24A 2.5549 no . .
H19A H25A 2.5018 no . .
H19A H25B 3.5909 no . .
H19B H20 2.3823 no . .
H19B H21A 2.4879 no . .
H19B H21B 3.5805 no . .
H19B H25A 3.5893 no . .
H20 H21A 2.3902 no . .
H20 H21B 2.3882 no . .
H20 H25A 2.3929 no . .
H20 H25B 2.3790 no . .
H21A H22B 3.5649 no . .
H21B H22A 3.5693 no . .
H21B H22B 2.4664 no . .
H21B H25B 2.5774 no . .
H22A H23 2.3746 no . .
H22A H24B 2.5365 no . .
H22A H25B 3.5965 no . .
H22B H23 2.4002 no . .
H22B H25A 3.5917 no . .
H22B H25B 2.5065 no . .
H23 H24A 2.3755 no . .
H23 H24B 2.3840 no . .
H23 H25A 2.3942 no . .
H23 H25B 2.3868 no . .
H24A H25A 2.5174 no . .
H24A H25B 3.5988 no . .
H24B H25A 3.5987 no . .
Se1 H7A 3.4829 no . 1_565
Se1 H9A 3.3459 no . 1_565
Se1 H19B 3.2246 no . 4_664
Se1 H21A 3.1166 no . 4_664
Se1 H25A 3.2664 no . 4_674
N2 H14B 3.4170 no . 2_555
N2 H22B 3.4767 no . 1_545
N2 H23 3.5104 no . 1_545
N5 H14B 3.5531 no . 2_555
N5 H23 3.3409 no . 1_545
C1 H23 3.3857 no . 1_545
C3 H9B 3.3186 no . 2_555
C3 H14B 2.9572 no . 2_555
C3 H18 3.2449 no . 4_665
C3 H22B 3.1619 no . 1_545
C3 H23 3.5409 no . 1_545
C3 H25B 3.4114 no . 1_545
C4 H14B 3.0534 no . 2_555
C4 H17A 3.3214 no . 4_665
C4 H18 3.2045 no . 4_665
C4 H23 3.4399 no . 1_545
C4 H25B 3.0928 no . 1_545
C7 H19B 3.5852 no . 4_664
C7 H20 3.0078 no . 4_664
C7 H22A 3.3681 no . 1_545
C8 H11B 3.3831 no . 2_544
C8 H12A 3.5960 no . 2_544
C9 H11B 3.5305 no . 2_544
C9 H12A 3.3299 no . 1_545
C9 H12B 3.0402 no . 1_545
C9 H18 3.4849 no . 3_455
C10 H14A 3.1368 no . 2_545
C10 H19B 3.2584 no . 3_455
C11 H8 3.5348 no . 2_555
C11 H14A 3.0752 no . 2_545
C12 H9A 2.9230 no . 1_565
C12 H9B 3.4307 no . 1_565
C12 H19A 3.5851 no . 3_465
C13 H19A 3.4127 no . 3_465
C13 H24A 3.0751 no . 3_465
C14 H10 3.4168 no . 2_554
C14 H11A 3.3349 no . 2_554
C14 H12A 3.5997 no . 2_544
C15 H18 3.5806 no . 3_455
C15 H19A 3.3496 no . 3_465
C15 H19B 3.4273 no . 3_455
C15 H24A 3.0577 no . 3_465
C15 H25A 3.3030 no . 3_465
C17 H4 3.0440 no . 4_664
C17 H15A 3.4355 no . 3_555
C17 H23 3.4063 no . 1_545
C18 H3 3.5987 no . 4_664
C18 H4 3.2105 no . 4_664
C18 H9B 3.5237 no . 3_555
C18 H13 3.4304 no . 3_565
C18 H15A 3.3523 no . 3_555
C19 H7B 3.1041 no . 4_665
C19 H10 3.1457 no . 3_555
C19 H15B 3.4933 no . 3_565
C20 H7A 3.5575 no . 4_665
C20 H7B 3.2177 no . 4_665
C20 H24B 3.0693 no . 4_675
C21 H17A 3.5581 no . 4_665
C21 H23 3.5806 no . 4_675
C21 H24B 3.1087 no . 4_675
C22 H7A 3.0190 no . 1_565
C22 H20 3.5102 no . 4_674
C23 H17B 3.4107 no . 1_565
C23 H20 3.4835 no . 4_674
C23 H21B 3.4935 no . 4_674
C24 H13 3.1665 no . 3_565
C24 H20 3.5371 no . 4_674
C24 H21B 2.9139 no . 4_674
C24 H25B 3.1113 no . 4_674
C25 H15B 3.4994 no . 3_565
C25 H17B 3.4095 no . 1_565
C25 H24B 2.9265 no . 4_675
H3 C18 3.5987 no . 4_665
H3 H9B 2.7166 no . 2_555
H3 H13 3.2241 no . 2_545
H3 H14B 3.1247 no . 2_555
H3 H18 2.7280 no . 4_665
H3 H22B 3.0458 no . 1_545
H3 H24B 3.4881 no . 4_665
H3 H25B 3.5100 no . 1_545
H4 C17 3.0440 no . 4_665
H4 C18 3.2105 no . 4_665
H4 H14B 3.2927 no . 2_555
H4 H15A 3.3843 no . 2_555
H4 H17A 2.3994 no . 4_665
H4 H17B 3.2064 no . 4_665
H4 H18 2.6434 no . 4_665
H4 H24B 3.2623 no . 4_665
H4 H25B 2.9182 no . 1_545
H7A Se1 3.4829 no . 1_545
H7A C20 3.5575 no . 4_664
H7A C22 3.0190 no . 1_545
H7A H20 2.6148 no . 4_664
H7A H22A 2.3950 no . 1_545
H7A H22B 2.8119 no . 1_545
H7A H23 3.4134 no . 1_545
H7B C19 3.1041 no . 4_664
H7B C20 3.2177 no . 4_664
H7B H10 3.3674 no . 2_554
H7B H19A 3.0230 no . 4_664
H7B H19B 2.6721 no . 4_664
H7B H20 2.5204 no . 4_664
H8 C11 3.5348 no . 2_544
H8 H11B 2.6073 no . 2_544
H8 H12A 2.7944 no . 2_544
H8 H15B 3.1092 no . 2_544
H8 H19A 3.0208 no . 4_664
H9A Se1 3.3459 no . 1_545
H9A C12 2.9230 no . 1_545
H9A H12A 2.6627 no . 1_545
H9A H12B 2.3045 no . 1_545
H9A H14A 3.5147 no . 2_545
H9B C3 3.3186 no . 2_544
H9B C12 3.4307 no . 1_545
H9B C18 3.5237 no . 3_455
H9B H3 2.7166 no . 2_544
H9B H11B 3.0495 no . 2_544
H9B H12A 3.2152 no . 1_545
H9B H12B 2.9169 no . 1_545
H9B H13 3.2259 no . 1_545
H9B H18 2.6336 no . 3_455
H9B H19A 3.5149 no . 3_455
H9B H19B 3.5794 no . 3_455
H10 C14 3.4168 no . 2_545
H10 C19 3.1457 no . 3_455
H10 H7B 3.3674 no . 2_545
H10 H12A 3.4388 no . 1_545
H10 H14A 2.4466 no . 2_545
H10 H18 3.3698 no . 3_455
H10 H19A 3.0536 no . 3_455
H10 H19B 2.4563 no . 3_455
H11A C14 3.3349 no . 2_545
H11A H13 3.4216 no . 2_545
H11A H14A 2.5956 no . 2_545
H11A H14B 3.3294 no . 2_545
H11A H22B 2.8656 no . 1_545
H11B C8 3.3831 no . 2_555
H11B C9 3.5305 no . 2_555
H11B H8 2.6073 no . 2_555
H11B H9B 3.0495 no . 2_555
H11B H12B 3.3923 no . 2_545
H11B H14A 3.0878 no . 2_545
H11B H14B 3.5778 no . 2_555
H12A C8 3.5960 no . 2_555
H12A C9 3.3299 no . 1_565
H12A C14 3.5997 no . 2_555
H12A H8 2.7944 no . 2_555
H12A H9A 2.6627 no . 1_565
H12A H9B 3.2152 no . 1_565
H12A H10 3.4388 no . 1_565
H12A H14A 3.3447 no . 2_555
H12A H14B 3.3247 no . 2_555
H12A H19A 2.9032 no . 3_465
H12B C9 3.0402 no . 1_565
H12B H9A 2.3045 no . 1_565
H12B H9B 2.9169 no . 1_565
H12B H11B 3.3923 no . 2_554
H13 C18 3.4304 no . 3_465
H13 C24 3.1665 no . 3_465
H13 H3 3.2241 no . 2_554
H13 H9B 3.2259 no . 1_565
H13 H11A 3.4216 no . 2_554
H13 H18 3.0712 no . 3_465
H13 H19A 2.9402 no . 3_465
H13 H24A 2.3247 no . 3_465
H13 H24B 3.5669 no . 3_465
H14A C10 3.1368 no . 2_554
H14A C11 3.0752 no . 2_554
H14A H9A 3.5147 no . 2_554
H14A H10 2.4466 no . 2_554
H14A H11A 2.5956 no . 2_554
H14A H11B 3.0878 no . 2_554
H14A H12A 3.3447 no . 2_544
H14B N2 3.4170 no . 2_544
H14B N5 3.5531 no . 2_544
H14B C3 2.9572 no . 2_544
H14B C4 3.0534 no . 2_544
H14B H3 3.1247 no . 2_544
H14B H4 3.2927 no . 2_544
H14B H11A 3.3294 no . 2_554
H14B H11B 3.5778 no . 2_544
H14B H12A 3.3247 no . 2_544
H15A C17 3.4355 no . 3_455
H15A C18 3.3523 no . 3_455
H15A H4 3.3843 no . 2_544
H15A H17B 2.7914 no . 3_455
H15A H18 2.7612 no . 3_455
H15A H19B 3.0148 no . 3_455
H15A H24A 2.7482 no . 3_465
H15A H25A 3.1114 no . 3_465
H15B C19 3.4933 no . 3_465
H15B C25 3.4994 no . 3_465
H15B H8 3.1092 no . 2_555
H15B H19A 2.6040 no . 3_465
H15B H19B 3.4707 no . 3_455
H15B H24A 2.9186 no . 3_465
H15B H25A 2.6071 no . 3_465
H17A C4 3.3214 no . 4_664
H17A C21 3.5581 no . 4_664
H17A H4 2.3994 no . 4_664
H17A H21A 2.7926 no . 4_664
H17A H21B 3.4235 no . 4_664
H17A H23 3.3226 no . 1_545
H17A H25B 3.1891 no . 4_674
H17B C23 3.4107 no . 1_545
H17B C25 3.4095 no . 1_545
H17B H4 3.2064 no . 4_664
H17B H15A 2.7914 no . 3_555
H17B H23 2.7130 no . 1_545
H17B H24A 3.5244 no . 1_545
H17B H25A 2.8662 no . 1_545
H17B H25B 3.4979 no . 1_545
H18 C3 3.2449 no . 4_664
H18 C4 3.2045 no . 4_664
H18 C9 3.4849 no . 3_555
H18 C15 3.5806 no . 3_555
H18 H3 2.7280 no . 4_664
H18 H4 2.6434 no . 4_664
H18 H9B 2.6336 no . 3_555
H18 H10 3.3698 no . 3_555
H18 H13 3.0712 no . 3_565
H18 H15A 2.7612 no . 3_555
H19A C12 3.5851 no . 3_565
H19A C13 3.4127 no . 3_565
H19A C15 3.3496 no . 3_565
H19A H7B 3.0230 no . 4_665
H19A H8 3.0208 no . 4_665
H19A H9B 3.5149 no . 3_555
H19A H10 3.0536 no . 3_555
H19A H12A 2.9032 no . 3_565
H19A H13 2.9402 no . 3_565
H19A H15B 2.6040 no . 3_565
H19B Se1 3.2246 no . 4_665
H19B C7 3.5852 no . 4_665
H19B C10 3.2584 no . 3_555
H19B C15 3.4273 no . 3_555
H19B H7B 2.6721 no . 4_665
H19B H9B 3.5794 no . 3_555
H19B H10 2.4563 no . 3_555
H19B H15A 3.0148 no . 3_555
H19B H15B 3.4707 no . 3_555
H20 C7 3.0078 no . 4_665
H20 C22 3.5102 no . 4_675
H20 C23 3.4835 no . 4_675
H20 C24 3.5371 no . 4_675
H20 H7A 2.6148 no . 4_665
H20 H7B 2.5204 no . 4_665
H20 H22A 2.7601 no . 4_675
H20 H23 3.0190 no . 4_675
H20 H24B 2.8069 no . 4_675
H21A Se1 3.1166 no . 4_665
H21A H17A 2.7926 no . 4_665
H21A H23 3.5421 no . 4_675
H21A H25A 3.5260 no . 1_545
H21A H25B 3.5104 no . 1_545
H21B C23 3.4935 no . 4_675
H21B C24 2.9139 no . 4_675
H21B H17A 3.4235 no . 4_665
H21B H23 3.0313 no . 4_675
H21B H24A 2.7071 no . 4_675
H21B H24B 2.3735 no . 4_675
H22A C7 3.3681 no . 1_565
H22A H7A 2.3950 no . 1_565
H22A H20 2.7601 no . 4_674
H22A H25B 3.4332 no . 4_674
H22B N2 3.4767 no . 1_565
H22B C3 3.1619 no . 1_565
H22B H3 3.0458 no . 1_565
H22B H7A 2.8119 no . 1_565
H22B H11A 2.8656 no . 1_565
H22B H24B 3.4503 no . 4_675
H23 N2 3.5104 no . 1_565
H23 N5 3.3409 no . 1_565
H23 C1 3.3857 no . 1_565
H23 C3 3.5409 no . 1_565
H23 C4 3.4399 no . 1_565
H23 C17 3.4063 no . 1_565
H23 C21 3.5806 no . 4_674
H23 H7A 3.4134 no . 1_565
H23 H17A 3.3226 no . 1_565
H23 H17B 2.7130 no . 1_565
H23 H20 3.0190 no . 4_674
H23 H21A 3.5421 no . 4_674
H23 H21B 3.0313 no . 4_674
H24A C13 3.0751 no . 3_565
H24A C15 3.0577 no . 3_565
H24A H13 2.3247 no . 3_565
H24A H15A 2.7482 no . 3_565
H24A H15B 2.9186 no . 3_565
H24A H17B 3.5244 no . 1_565
H24A H21B 2.7071 no . 4_674
H24A H25B 3.5373 no . 4_674
H24B C20 3.0693 no . 4_674
H24B C21 3.1087 no . 4_674
H24B C25 2.9265 no . 4_674
H24B H3 3.4881 no . 4_664
H24B H4 3.2623 no . 4_664
H24B H13 3.5669 no . 3_565
H24B H20 2.8069 no . 4_674
H24B H21B 2.3735 no . 4_674
H24B H22B 3.4503 no . 4_674
H24B H25A 3.4786 no . 4_674
H24B H25B 2.1259 no . 4_674
H25A Se1 3.2664 no . 4_675
H25A C15 3.3030 no . 3_565
H25A H15A 3.1114 no . 3_565
H25A H15B 2.6071 no . 3_565
H25A H17B 2.8662 no . 1_565
H25A H21A 3.5260 no . 1_565
H25A H24B 3.4786 no . 4_675
H25B C3 3.4114 no . 1_565
H25B C4 3.0928 no . 1_565
H25B C24 3.1113 no . 4_675
H25B H3 3.5100 no . 1_565
H25B H4 2.9182 no . 1_565
H25B H17A 3.1891 no . 4_675
H25B H17B 3.4979 no . 1_565
H25B H21A 3.5104 no . 1_565
H25B H22A 3.4332 no . 4_675
H25B H24A 3.5373 no . 4_675
H25B H24B 2.1259 no . 4_675

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_chemical_name_systematic        '[Se(IAd)]'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, pentane'
####################################################################### 
# 
# 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_[Se(ICy)]
_database_code_depnum_ccdc_archive 'CCDC 1024808'
_audit_update_record             
;
2014-09-17 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C15 H24 N2 Se'
_chemical_formula_moiety         'C15 H24 N2 Se'
_chemical_formula_weight         311.33
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.8147(15)
_cell_length_b                   11.1443(13)
_cell_length_c                   12.2088(14)
_cell_angle_alpha                90.0000
_cell_angle_beta                 108.210(3)
_cell_angle_gamma                90.0000
_cell_volume                     1527.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4415
_cell_measurement_theta_min      1.81
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648.00
_exptl_absorpt_coefficient_mu    2.446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_T_max  0.907

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            18233
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_theta_max         25.388
_diffrn_reflns_theta_min         1.815
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2808
_reflns_number_gt                2397
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0998
_refine_ls_wR_factor_gt          0.0962
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2808
_refine_ls_number_parameters     163
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0730P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.89
_refine_diff_density_min         -0.42
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.21807(2) 0.04854(2) 0.23867(2) 0.03102(13) Uani 1 4 d . . .
N2 N 0.08102(17) 0.26068(18) 0.24891(17) 0.0288(4) Uani 1 4 d . . .
N5 N 0.23392(18) 0.23892(18) 0.40225(17) 0.0307(5) Uani 1 4 d . . .
C1 C 0.1759(2) 0.1886(2) 0.2978(2) 0.0267(5) Uani 1 4 d . . .
C3 C 0.0782(2) 0.3532(2) 0.3236(2) 0.0339(6) Uani 1 4 d . . .
C4 C 0.1722(2) 0.3392(2) 0.4185(2) 0.0347(6) Uani 1 4 d . . .
C6 C -0.0079(2) 0.2407(2) 0.1363(2) 0.0298(5) Uani 1 4 d . . .
C7 C -0.1229(2) 0.1896(2) 0.1482(2) 0.0336(6) Uani 1 4 d . . .
C8 C -0.2126(3) 0.1658(3) 0.0293(3) 0.0477(7) Uani 1 4 d . . .
C9 C -0.2359(3) 0.2793(3) -0.0433(3) 0.0486(8) Uani 1 4 d . . .
C10 C -0.1206(3) 0.3302(3) -0.0539(2) 0.0429(7) Uani 1 4 d . . .
C11 C -0.0320(2) 0.3555(2) 0.0639(2) 0.0360(6) Uani 1 4 d . . .
C12 C 0.3379(2) 0.1867(2) 0.4896(2) 0.0317(5) Uani 1 4 d . . .
C13 C 0.2970(2) 0.1190(2) 0.5782(3) 0.0405(6) Uani 1 4 d . . .
C14 C 0.4016(3) 0.0614(3) 0.6693(3) 0.0527(8) Uani 1 4 d . . .
C15 C 0.4943(3) 0.1562(3) 0.7279(3) 0.0460(7) Uani 1 4 d . . .
C16 C 0.5343(3) 0.2236(3) 0.6381(3) 0.0470(7) Uani 1 4 d . . .
C17 C 0.4299(2) 0.2823(3) 0.5474(2) 0.0412(7) Uani 1 4 d . . .
H3 H 0.0203 0.41519 0.31005 0.0406 Uiso 1 4 calc R . .
H4 H 0.19272 0.38917 0.4849 0.0416 Uiso 1 4 calc R . .
H6 H 0.02535 0.17997 0.09433 0.0358 Uiso 1 4 calc R . .
H7A H -0.15732 0.24712 0.19094 0.0404 Uiso 1 4 calc R . .
H7B H -0.10567 0.11388 0.19272 0.0404 Uiso 1 4 calc R . .
H8A H -0.18129 0.10259 -0.01037 0.0573 Uiso 1 4 calc R . .
H8B H -0.28836 0.13663 0.03834 0.0573 Uiso 1 4 calc R . .
H9A H -0.29084 0.26103 -0.12113 0.0583 Uiso 1 4 calc R . .
H9B H -0.27451 0.33984 -0.00746 0.0583 Uiso 1 4 calc R . .
H10A H -0.13772 0.40549 -0.09916 0.0515 Uiso 1 4 calc R . .
H10B H -0.08545 0.2724 -0.09559 0.0515 Uiso 1 4 calc R . .
H11A H -0.06425 0.418 0.10357 0.0431 Uiso 1 4 calc R . .
H11B H 0.04343 0.3857 0.05498 0.0431 Uiso 1 4 calc R . .
H12 H 0.37638 0.12813 0.4503 0.0380 Uiso 1 4 calc R . .
H13A H 0.23954 0.056 0.53904 0.0486 Uiso 1 4 calc R . .
H13B H 0.25573 0.17502 0.61595 0.0486 Uiso 1 4 calc R . .
H14A H 0.43862 0.00008 0.63274 0.0633 Uiso 1 4 calc R . .
H14B H 0.37273 0.02103 0.72771 0.0633 Uiso 1 4 calc R . .
H15A H 0.45961 0.21323 0.77069 0.0552 Uiso 1 4 calc R . .
H15B H 0.56382 0.11691 0.78368 0.0552 Uiso 1 4 calc R . .
H16A H 0.57463 0.16712 0.59981 0.0564 Uiso 1 4 calc R . .
H16B H 0.59264 0.28611 0.67687 0.0564 Uiso 1 4 calc R . .
H17A H 0.45846 0.32277 0.48884 0.0495 Uiso 1 4 calc R . .
H17B H 0.39285 0.34346 0.58419 0.0495 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Se1 C1 1.852(2) yes . .
N2 C1 1.357(3) yes . .
N2 C3 1.383(3) yes . .
N2 C6 1.464(3) yes . .
N5 C1 1.366(3) yes . .
N5 C4 1.382(3) yes . .
N5 C12 1.472(3) yes . .
C3 C4 1.341(3) yes . .
C6 C7 1.521(4) yes . .
C6 C11 1.530(4) yes . .
C7 C8 1.530(4) yes . .
C8 C9 1.520(4) yes . .
C9 C10 1.517(5) yes . .
C10 C11 1.517(3) yes . .
C12 C13 1.516(4) yes . .
C12 C17 1.528(4) yes . .
C13 C14 1.522(4) yes . .
C14 C15 1.529(4) yes . .
C15 C16 1.521(5) yes . .
C16 C17 1.524(4) yes . .
C3 H3 0.950 no . .
C4 H4 0.950 no . .
C6 H6 1.000 no . .
C7 H7A 0.990 no . .
C7 H7B 0.990 no . .
C8 H8A 0.990 no . .
C8 H8B 0.990 no . .
C9 H9A 0.990 no . .
C9 H9B 0.990 no . .
C10 H10A 0.990 no . .
C10 H10B 0.990 no . .
C11 H11A 0.990 no . .
C11 H11B 0.990 no . .
C12 H12 1.000 no . .
C13 H13A 0.990 no . .
C13 H13B 0.990 no . .
C14 H14A 0.990 no . .
C14 H14B 0.990 no . .
C15 H15A 0.990 no . .
C15 H15B 0.990 no . .
C16 H16A 0.990 no . .
C16 H16B 0.990 no . .
C17 H17A 0.990 no . .
C17 H17B 0.990 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N2 C3 109.77(18) yes . . .
C1 N2 C6 125.1(2) yes . . .
C3 N2 C6 125.1(2) yes . . .
C1 N5 C4 109.47(18) yes . . .
C1 N5 C12 125.2(2) yes . . .
C4 N5 C12 125.0(2) yes . . .
Se1 C1 N2 127.85(16) yes . . .
Se1 C1 N5 126.35(16) yes . . .
N2 C1 N5 105.8(2) yes . . .
N2 C3 C4 107.4(2) yes . . .
N5 C4 C3 107.5(2) yes . . .
N2 C6 C7 111.5(2) yes . . .
N2 C6 C11 111.35(19) yes . . .
C7 C6 C11 110.97(19) yes . . .
C6 C7 C8 110.4(2) yes . . .
C7 C8 C9 110.8(2) yes . . .
C8 C9 C10 110.9(2) yes . . .
C9 C10 C11 111.2(3) yes . . .
C6 C11 C10 109.9(2) yes . . .
N5 C12 C13 109.5(2) yes . . .
N5 C12 C17 111.8(2) yes . . .
C13 C12 C17 110.9(2) yes . . .
C12 C13 C14 111.4(3) yes . . .
C13 C14 C15 110.5(2) yes . . .
C14 C15 C16 110.0(3) yes . . .
C15 C16 C17 111.8(2) yes . . .
C12 C17 C16 109.5(2) yes . . .
N2 C3 H3 126.287 no . . .
C4 C3 H3 126.286 no . . .
N5 C4 H4 126.241 no . . .
C3 C4 H4 126.240 no . . .
N2 C6 H6 107.593 no . . .
C7 C6 H6 107.596 no . . .
C11 C6 H6 107.588 no . . .
C6 C7 H7A 109.572 no . . .
C6 C7 H7B 109.572 no . . .
C8 C7 H7A 109.584 no . . .
C8 C7 H7B 109.580 no . . .
H7A C7 H7B 108.118 no . . .
C7 C8 H8A 109.494 no . . .
C7 C8 H8B 109.483 no . . .
C9 C8 H8A 109.500 no . . .
C9 C8 H8B 109.491 no . . .
H8A C8 H8B 108.067 no . . .
C8 C9 H9A 109.450 no . . .
C8 C9 H9B 109.448 no . . .
C10 C9 H9A 109.453 no . . .
C10 C9 H9B 109.449 no . . .
H9A C9 H9B 108.042 no . . .
C9 C10 H10A 109.404 no . . .
C9 C10 H10B 109.403 no . . .
C11 C10 H10A 109.406 no . . .
C11 C10 H10B 109.399 no . . .
H10A C10 H10B 108.014 no . . .
C6 C11 H11A 109.687 no . . .
C6 C11 H11B 109.686 no . . .
C10 C11 H11A 109.676 no . . .
C10 C11 H11B 109.683 no . . .
H11A C11 H11B 108.177 no . . .
N5 C12 H12 108.180 no . . .
C13 C12 H12 108.179 no . . .
C17 C12 H12 108.179 no . . .
C12 C13 H13A 109.361 no . . .
C12 C13 H13B 109.358 no . . .
C14 C13 H13A 109.355 no . . .
C14 C13 H13B 109.354 no . . .
H13A C13 H13B 107.985 no . . .
C13 C14 H14A 109.547 no . . .
C13 C14 H14B 109.554 no . . .
C15 C14 H14A 109.551 no . . .
C15 C14 H14B 109.542 no . . .
H14A C14 H14B 108.099 no . . .
C14 C15 H15A 109.654 no . . .
C14 C15 H15B 109.649 no . . .
C16 C15 H15A 109.657 no . . .
C16 C15 H15B 109.649 no . . .
H15A C15 H15B 108.163 no . . .
C15 C16 H16A 109.251 no . . .
C15 C16 H16B 109.244 no . . .
C17 C16 H16A 109.253 no . . .
C17 C16 H16B 109.253 no . . .
H16A C16 H16B 107.938 no . . .
C12 C17 H17A 109.772 no . . .
C12 C17 H17B 109.776 no . . .
C16 C17 H17A 109.770 no . . .
C16 C17 H17B 109.775 no . . .
H17A C17 H17B 108.229 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N2 C3 C4 0.6(3) no . . . .
C3 N2 C1 Se1 177.0(2) no . . . .
C3 N2 C1 N5 -1.6(3) no . . . .
C1 N2 C6 C7 102.5(3) no . . . .
C1 N2 C6 C11 -132.9(2) no . . . .
C6 N2 C1 Se1 -0.5(4) no . . . .
C6 N2 C1 N5 -179.1(2) no . . . .
C3 N2 C6 C7 -74.6(3) no . . . .
C3 N2 C6 C11 49.9(3) no . . . .
C6 N2 C3 C4 178.2(2) no . . . .
C1 N5 C4 C3 -1.6(3) no . . . .
C4 N5 C1 Se1 -176.7(2) no . . . .
C4 N5 C1 N2 2.0(3) no . . . .
C1 N5 C12 C13 -96.8(3) no . . . .
C1 N5 C12 C17 139.9(2) no . . . .
C12 N5 C1 Se1 -3.3(4) no . . . .
C12 N5 C1 N2 175.3(2) no . . . .
C4 N5 C12 C13 75.6(3) no . . . .
C4 N5 C12 C17 -47.7(3) no . . . .
C12 N5 C4 C3 -175.0(2) no . . . .
N2 C3 C4 N5 0.6(3) no . . . .
N2 C6 C7 C8 -178.15(17) no . . . .
N2 C6 C11 C10 177.67(19) no . . . .
C7 C6 C11 C10 -57.5(3) no . . . .
C11 C6 C7 C8 57.1(3) no . . . .
C6 C7 C8 C9 -56.3(3) no . . . .
C7 C8 C9 C10 56.2(3) no . . . .
C8 C9 C10 C11 -57.1(3) no . . . .
C9 C10 C11 C6 57.2(3) no . . . .
N5 C12 C13 C14 178.96(18) no . . . .
N5 C12 C17 C16 179.1(2) no . . . .
C13 C12 C17 C16 56.6(3) no . . . .
C17 C12 C13 C14 -57.2(3) no . . . .
C12 C13 C14 C15 56.7(3) no . . . .
C13 C14 C15 C16 -56.1(4) no . . . .
C14 C15 C16 C17 57.4(3) no . . . .
C15 C16 C17 C12 -57.3(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Se1 C6 3.345(2) no . .
Se1 C12 3.324(2) no . .
N2 C12 3.599(3) no . .
N5 C6 3.593(3) no . .
C1 C7 3.431(3) no . .
C1 C13 3.363(4) no . .
C3 C7 3.220(3) no . .
C3 C11 3.027(4) no . .
C4 C13 3.194(4) no . .
C4 C17 3.025(4) no . .
C6 C9 2.925(3) no . .
C7 C10 2.930(4) no . .
C8 C11 2.939(4) no . .
C12 C15 2.938(4) no . .
C13 C16 2.911(4) no . .
C14 C17 2.948(5) no . .
Se1 H6 2.8156 no . .
Se1 H12 2.8179 no . .
Se1 H13A 3.5969 no . .
N2 H4 3.1172 no . .
N2 H7A 2.6847 no . .
N2 H7B 2.6583 no . .
N2 H11A 2.6953 no . .
N2 H11B 2.6621 no . .
N5 H3 3.1177 no . .
N5 H13A 2.6229 no . .
N5 H13B 2.6382 no . .
N5 H17A 2.6973 no . .
N5 H17B 2.6852 no . .
C1 H3 3.1549 no . .
C1 H4 3.1579 no . .
C1 H6 2.5656 no . .
C1 H7B 3.2772 no . .
C1 H12 2.6026 no . .
C1 H13A 3.1686 no . .
C3 H6 3.2950 no . .
C3 H7A 2.9910 no . .
C3 H7B 3.4949 no . .
C3 H11A 2.7828 no . .
C3 H11B 3.1956 no . .
C4 H12 3.3042 no . .
C4 H13A 3.4682 no . .
C4 H13B 2.9403 no . .
C4 H17A 3.2237 no . .
C4 H17B 2.7554 no . .
C6 H3 2.8203 no . .
C6 H8A 2.7341 no . .
C6 H8B 3.3577 no . .
C6 H9B 3.2811 no . .
C6 H10A 3.3513 no . .
C6 H10B 2.7121 no . .
C7 H3 3.3157 no . .
C7 H9A 3.3627 no . .
C7 H9B 2.7379 no . .
C7 H10B 3.2759 no . .
C7 H11A 2.7368 no . .
C7 H11B 3.3661 no . .
C8 H6 2.6769 no . .
C8 H10A 3.3535 no . .
C8 H10B 2.7251 no . .
C8 H11A 3.2865 no . .
C9 H6 3.2145 no . .
C9 H7A 2.7408 no . .
C9 H7B 3.3617 no . .
C9 H11A 2.7282 no . .
C9 H11B 3.3554 no . .
C10 H6 2.6649 no . .
C10 H7A 3.2846 no . .
C10 H8A 2.7331 no . .
C10 H8B 3.3533 no . .
C11 H3 2.9484 no . .
C11 H7A 2.7369 no . .
C11 H7B 3.3668 no . .
C11 H8A 3.2981 no . .
C11 H9A 3.3537 no . .
C11 H9B 2.7275 no . .
C12 H4 2.8238 no . .
C12 H14A 2.7377 no . .
C12 H14B 3.3584 no . .
C12 H15A 3.2935 no . .
C12 H16A 2.7075 no . .
C12 H16B 3.3487 no . .
C13 H4 3.3170 no . .
C13 H15A 2.7374 no . .
C13 H15B 3.3598 no . .
C13 H16A 3.2519 no . .
C13 H17A 3.3594 no . .
C13 H17B 2.7371 no . .
C14 H12 2.7000 no . .
C14 H16A 2.7148 no . .
C14 H16B 3.3530 no . .
C14 H17B 3.3016 no . .
C15 H12 3.2514 no . .
C15 H13A 3.3591 no . .
C15 H13B 2.7294 no . .
C15 H17A 3.3721 no . .
C15 H17B 2.7490 no . .
C16 H12 2.6827 no . .
C16 H13B 3.2628 no . .
C16 H14A 2.7279 no . .
C16 H14B 3.3533 no . .
C17 H4 2.9178 no . .
C17 H13A 3.3590 no . .
C17 H13B 2.7272 no . .
C17 H14A 3.3046 no . .
C17 H15A 2.7474 no . .
C17 H15B 3.3719 no . .
H3 H4 2.4643 no . .
H3 H7A 2.8495 no . .
H3 H11A 2.4041 no . .
H3 H11B 3.2268 no . .
H4 H13B 2.8399 no . .
H4 H17A 3.2114 no . .
H4 H17B 2.3512 no . .
H6 H7A 2.8636 no . .
H6 H7B 2.3545 no . .
H6 H8A 2.5274 no . .
H6 H8B 3.5853 no . .
H6 H10A 3.5727 no . .
H6 H10B 2.5008 no . .
H6 H11A 2.8714 no . .
H6 H11B 2.3658 no . .
H7A H8A 2.8775 no . .
H7A H8B 2.3625 no . .
H7A H9B 2.5992 no . .
H7A H11A 2.5897 no . .
H7B H8A 2.3616 no . .
H7B H8B 2.3944 no . .
H8A H9A 2.3511 no . .
H8A H9B 2.8687 no . .
H8A H10B 2.5850 no . .
H8B H9A 2.3828 no . .
H8B H9B 2.3506 no . .
H9A H10A 2.3734 no . .
H9A H10B 2.3514 no . .
H9B H10A 2.3519 no . .
H9B H10B 2.8660 no . .
H9B H11A 2.5812 no . .
H10A H11A 2.3572 no . .
H10A H11B 2.3777 no . .
H10B H11A 2.8683 no . .
H10B H11B 2.3543 no . .
H12 H13A 2.3513 no . .
H12 H13B 2.8630 no . .
H12 H14A 2.5524 no . .
H12 H16A 2.5169 no . .
H12 H16B 3.5864 no . .
H12 H17A 2.3626 no . .
H12 H17B 2.8757 no . .
H13A H14A 2.3553 no . .
H13A H14B 2.3809 no . .
H13B H14A 2.8697 no . .
H13B H14B 2.3535 no . .
H13B H15A 2.5901 no . .
H13B H17B 2.5867 no . .
H14A H15A 2.8774 no . .
H14A H15B 2.3612 no . .
H14A H16A 2.5716 no . .
H14B H15A 2.3622 no . .
H14B H15B 2.3961 no . .
H15A H16A 2.8697 no . .
H15A H16B 2.3595 no . .
H15A H17B 2.6059 no . .
H15B H16A 2.3554 no . .
H15B H16B 2.3769 no . .
H16A H17A 2.3592 no . .
H16A H17B 2.8731 no . .
H16B H17A 2.3823 no . .
H16B H17B 2.3646 no . .
Se1 H3 3.0735 no . 2_545
Se1 H4 3.0969 no . 4_554
Se1 H7A 3.5948 no . 2_545
Se1 H8A 3.1682 no . 3_555
Se1 H11A 3.3640 no . 2_545
Se1 H13B 3.5143 no . 4_554
Se1 H15B 3.2487 no . 3_656
Se1 H16A 3.5560 no . 3_656
Se1 H17B 3.4211 no . 4_554
N2 H10B 3.1531 no . 4_555
N2 H13B 3.0828 no . 4_554
N5 H15A 3.5568 no . 4_554
C1 H13B 3.0718 no . 4_554
C3 H6 3.5698 no . 4_555
C3 H7B 2.9371 no . 2_555
C3 H8A 3.5601 no . 2_555
C3 H10B 2.8042 no . 4_555
C4 H6 3.1610 no . 4_555
C4 H7B 3.3413 no . 2_555
C4 H8A 3.1317 no . 2_555
C4 H8B 3.5627 no . 2_555
C4 H10B 3.2431 no . 4_555
C4 H11B 3.5998 no . 4_555
C6 H13B 3.3364 no . 4_554
C7 H3 3.2707 no . 2_545
C7 H10A 3.3170 no . 4_555
C7 H10B 3.0481 no . 4_555
C7 H16B 3.4964 no . 4_454
C8 H4 3.1008 no . 2_545
C8 H15B 3.3638 no . 1_454
C8 H16A 3.4464 no . 4_454
C8 H16B 3.3789 no . 4_454
C9 H13A 3.0843 no . 2_555
C9 H14A 3.3687 no . 2_555
C9 H14B 3.5584 no . 2_555
C9 H15B 3.1959 no . 1_454
C9 H16A 3.2969 no . 4_454
C9 H16B 3.3843 no . 1_454
C10 H7A 3.1296 no . 4_554
C10 H7B 3.2145 no . 4_554
C10 H11B 3.2956 no . 3_565
C10 H13A 2.9147 no . 2_555
C11 H10A 3.2805 no . 3_565
C11 H11B 3.2128 no . 3_565
C11 H13A 3.2649 no . 2_555
C11 H13A 3.4592 no . 4_554
C11 H13B 3.2749 no . 4_554
C12 H15A 3.5861 no . 4_554
C13 H9B 3.2176 no . 2_545
C13 H10A 3.0937 no . 2_545
C13 H11B 2.9203 no . 4_555
C14 H9A 3.5755 no . 2_545
C14 H9B 3.2251 no . 2_545
C14 H10A 3.4356 no . 2_545
C14 H16B 3.5872 no . 2_646
C15 H9A 2.8781 no . 1_656
C15 H17A 3.3510 no . 4_555
C16 H7A 3.5106 no . 4_655
C16 H8B 3.1451 no . 4_655
C16 H9A 3.0474 no . 1_656
C16 H9B 3.3564 no . 4_655
C17 H8B 3.4847 no . 4_655
C17 H15A 3.5046 no . 4_554
H3 Se1 3.0735 no . 2_555
H3 C7 3.2707 no . 2_555
H3 H6 3.2794 no . 2_555
H3 H7B 2.4378 no . 2_555
H3 H8A 3.3247 no . 2_555
H3 H10B 2.8563 no . 4_555
H4 Se1 3.0969 no . 4_555
H4 C8 3.1008 no . 2_555
H4 H6 2.8178 no . 4_555
H4 H7B 3.2615 no . 2_555
H4 H8A 2.4079 no . 2_555
H4 H8B 3.0270 no . 2_555
H6 C3 3.5698 no . 4_554
H6 C4 3.1610 no . 4_554
H6 H3 3.2794 no . 2_545
H6 H4 2.8178 no . 4_554
H6 H13B 3.1050 no . 4_554
H7A Se1 3.5948 no . 2_555
H7A C10 3.1296 no . 4_555
H7A C16 3.5106 no . 4_454
H7A H9A 3.1659 no . 4_555
H7A H10A 3.0236 no . 4_555
H7A H10B 2.4855 no . 4_555
H7A H16A 3.1589 no . 4_454
H7A H16B 2.9286 no . 4_454
H7B C3 2.9371 no . 2_545
H7B C4 3.3413 no . 2_545
H7B C10 3.2145 no . 4_555
H7B H3 2.4378 no . 2_545
H7B H4 3.2615 no . 2_545
H7B H10A 2.6921 no . 4_555
H7B H10B 2.8208 no . 4_555
H7B H11A 3.4439 no . 2_545
H8A Se1 3.1682 no . 3_555
H8A C3 3.5601 no . 2_545
H8A C4 3.1317 no . 2_545
H8A H3 3.3247 no . 2_545
H8A H4 2.4079 no . 2_545
H8A H15B 3.2686 no . 1_454
H8B C4 3.5627 no . 2_545
H8B C16 3.1451 no . 4_454
H8B C17 3.4847 no . 4_454
H8B H4 3.0270 no . 2_545
H8B H15B 3.0612 no . 1_454
H8B H16A 2.9540 no . 4_454
H8B H16B 2.6579 no . 4_454
H8B H17A 2.8961 no . 4_454
H9A C14 3.5755 no . 2_555
H9A C15 2.8781 no . 1_454
H9A C16 3.0474 no . 1_454
H9A H7A 3.1659 no . 4_554
H9A H13A 3.4348 no . 2_555
H9A H14A 3.1640 no . 2_555
H9A H14B 3.1997 no . 2_555
H9A H15A 2.8787 no . 1_454
H9A H15B 2.3731 no . 1_454
H9A H16A 3.4416 no . 1_454
H9A H16B 2.4359 no . 1_454
H9B C13 3.2176 no . 2_555
H9B C14 3.2251 no . 2_555
H9B C16 3.3564 no . 4_454
H9B H12 3.5753 no . 2_555
H9B H13A 2.4944 no . 2_555
H9B H14A 2.7266 no . 2_555
H9B H14B 3.2717 no . 2_555
H9B H16A 2.5213 no . 4_454
H9B H16B 3.4214 no . 4_454
H10A C7 3.3170 no . 4_554
H10A C11 3.2805 no . 3_565
H10A C13 3.0937 no . 2_555
H10A C14 3.4356 no . 2_555
H10A H7A 3.0236 no . 4_554
H10A H7B 2.6921 no . 4_554
H10A H11A 3.1059 no . 3_565
H10A H11B 2.5635 no . 3_565
H10A H13A 2.3133 no . 2_555
H10A H13B 3.2908 no . 2_555
H10A H14B 3.0178 no . 2_555
H10B N2 3.1531 no . 4_554
H10B C3 2.8042 no . 4_554
H10B C4 3.2431 no . 4_554
H10B C7 3.0481 no . 4_554
H10B H3 2.8563 no . 4_554
H10B H7A 2.4855 no . 4_554
H10B H7B 2.8208 no . 4_554
H11A Se1 3.3640 no . 2_555
H11A H7B 3.4439 no . 2_555
H11A H10A 3.1059 no . 3_565
H11A H11B 2.9817 no . 3_565
H11A H13A 2.7262 no . 2_555
H11B C4 3.5998 no . 4_554
H11B C10 3.2956 no . 3_565
H11B C11 3.2128 no . 3_565
H11B C13 2.9203 no . 4_554
H11B H10A 2.5635 no . 3_565
H11B H11A 2.9817 no . 3_565
H11B H11B 2.9128 no . 3_565
H11B H13A 2.4719 no . 4_554
H11B H13B 2.4772 no . 4_554
H12 H9B 3.5753 no . 2_545
H12 H14A 3.0384 no . 3_656
H12 H15A 3.2014 no . 4_554
H12 H16A 3.4289 no . 3_656
H13A C9 3.0843 no . 2_545
H13A C10 2.9147 no . 2_545
H13A C11 3.2649 no . 2_545
H13A C11 3.4592 no . 4_555
H13A H9A 3.4348 no . 2_545
H13A H9B 2.4944 no . 2_545
H13A H10A 2.3133 no . 2_545
H13A H11A 2.7262 no . 2_545
H13A H11B 2.4719 no . 4_555
H13B Se1 3.5143 no . 4_555
H13B N2 3.0828 no . 4_555
H13B C1 3.0718 no . 4_555
H13B C6 3.3364 no . 4_555
H13B C11 3.2749 no . 4_555
H13B H6 3.1050 no . 4_555
H13B H10A 3.2908 no . 2_545
H13B H11B 2.4772 no . 4_555
H14A C9 3.3687 no . 2_545
H14A H9A 3.1640 no . 2_545
H14A H9B 2.7266 no . 2_545
H14A H12 3.0384 no . 3_656
H14A H15A 3.4884 no . 2_646
H14A H16A 3.3585 no . 3_656
H14A H16B 3.4296 no . 2_646
H14B C9 3.5584 no . 2_545
H14B H9A 3.1997 no . 2_545
H14B H9B 3.2717 no . 2_545
H14B H10A 3.0178 no . 2_545
H14B H16B 2.8427 no . 2_646
H14B H17A 3.4931 no . 4_555
H14B H17B 3.5896 no . 2_646
H15A N5 3.5568 no . 4_555
H15A C12 3.5861 no . 4_555
H15A C17 3.5046 no . 4_555
H15A H9A 2.8787 no . 1_656
H15A H12 3.2014 no . 4_555
H15A H14A 3.4884 no . 2_656
H15A H17A 2.6976 no . 4_555
H15B Se1 3.2487 no . 3_656
H15B C8 3.3638 no . 1_656
H15B C9 3.1959 no . 1_656
H15B H8A 3.2686 no . 1_656
H15B H8B 3.0612 no . 1_656
H15B H9A 2.3731 no . 1_656
H15B H17A 3.1975 no . 4_555
H15B H17B 3.4110 no . 2_646
H16A Se1 3.5560 no . 3_656
H16A C8 3.4464 no . 4_655
H16A C9 3.2969 no . 4_655
H16A H7A 3.1589 no . 4_655
H16A H8B 2.9540 no . 4_655
H16A H9A 3.4416 no . 1_656
H16A H9B 2.5213 no . 4_655
H16A H12 3.4289 no . 3_656
H16A H14A 3.3585 no . 3_656
H16B C7 3.4964 no . 4_655
H16B C8 3.3789 no . 4_655
H16B C9 3.3843 no . 1_656
H16B C14 3.5872 no . 2_656
H16B H7A 2.9286 no . 4_655
H16B H8B 2.6579 no . 4_655
H16B H9A 2.4359 no . 1_656
H16B H9B 3.4214 no . 4_655
H16B H14A 3.4296 no . 2_656
H16B H14B 2.8427 no . 2_656
H17A C15 3.3510 no . 4_554
H17A H8B 2.8961 no . 4_655
H17A H14B 3.4931 no . 4_554
H17A H15A 2.6976 no . 4_554
H17A H15B 3.1975 no . 4_554
H17B Se1 3.4211 no . 4_555
H17B H14B 3.5896 no . 2_656
H17B H15B 3.4110 no . 2_656

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_chemical_name_systematic        '[Se(ICy)]'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone, pentane'
####################################################################### 
# 
# 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_[Se(IDD)]
_database_code_depnum_ccdc_archive 'CCDC 1024809'
_audit_update_record             
;
2014-09-17 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C27 H48 N2 Se'
_chemical_formula_moiety         'C27 H48 N2 Se'
_chemical_formula_weight         479.65
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   14.4058(13)
_cell_length_b                   7.4133(7)
_cell_length_c                   25.023(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.856(3)
_cell_angle_gamma                90.0000
_cell_volume                     2647.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7064
_cell_measurement_theta_min      1.64
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032.00
_exptl_absorpt_coefficient_mu    1.434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_T_max  0.958

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            31247
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_theta_max         25.392
_diffrn_reflns_theta_min         1.546
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).

    Restraints to bond distances and thermal parameters were required for one
    of the cyclododecane rings.
;
_reflns_number_total             4854
_reflns_number_gt                3880
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.2216
_refine_ls_wR_factor_gt          0.2078
_refine_ls_number_restraints     84
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4854
_refine_ls_number_parameters     271
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1301P)²+4.9833P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         1.71
_refine_diff_density_min         -0.54
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.62577(4) 0.10107(6) 0.85771(2) 0.0508(2) Uani 1 4 d . . .
N2 N 0.6399(3) 0.4323(5) 0.91777(18) 0.0493(10) Uani 1 4 d . . .
N5 N 0.5764(3) 0.4716(5) 0.83501(18) 0.0566(11) Uani 1 4 d . . .
C1 C 0.6130(3) 0.3440(6) 0.8705(2) 0.0456(11) Uani 1 4 d . . .
C3 C 0.6206(4) 0.6148(6) 0.9107(3) 0.0610(14) Uani 1 4 d . . .
C4 C 0.5809(5) 0.6387(7) 0.8601(3) 0.0647(15) Uani 1 4 d . . .
C6 C 0.6789(3) 0.3469(7) 0.96854(19) 0.0459(11) Uani 1 4 d . . .
C7 C 0.7826(3) 0.3962(7) 0.9828(2) 0.0529(12) Uani 1 4 d . . .
C8 C 0.8475(4) 0.2708(9) 0.9570(2) 0.0641(15) Uani 1 4 d . . .
C9 C 0.8491(4) 0.0771(9) 0.9763(2) 0.0683(18) Uani 1 4 d . . .
C10 C 0.8918(4) 0.0545(9) 1.0344(2) 0.0654(16) Uani 1 4 d . . .
C11 C 0.8793(4) -0.1352(9) 1.0572(3) 0.0719(17) Uani 1 4 d . . .
C12 C 0.7779(4) -0.1785(9) 1.0647(3) 0.0751(17) Uani 1 4 d . . .
C13 C 0.7419(5) -0.0732(10) 1.1101(3) 0.0746(17) Uani 1 4 d . . .
C14 C 0.6352(5) -0.0383(11) 1.1011(3) 0.0763(17) Uani 1 4 d . . .
C15 C 0.6025(4) 0.0842(9) 1.0544(3) 0.0657(16) Uani 1 4 d . . .
C16 C 0.6375(4) 0.2762(9) 1.0633(2) 0.0643(15) Uani 1 4 d . . .
C17 C 0.6196(4) 0.3955(8) 1.0130(2) 0.0603(14) Uani 1 4 d . . .
C18 C 0.5468(5) 0.4424(8) 0.7764(3) 0.0773(17) Uani 1 4 d . . .
C19 C 0.6250(5) 0.5433(9) 0.7409(3) 0.0827(18) Uani 1 4 d . . .
C20 C 0.6154(6) 0.4632(12) 0.6854(3) 0.101(2) Uani 1 4 d . . .
C21 C 0.6603(6) 0.2912(12) 0.6864(4) 0.113(3) Uani 1 4 d . . .
C22 C 0.6296(7) 0.1605(12) 0.6381(3) 0.105(2) Uani 1 4 d . . .
C23 C 0.5258(8) 0.1129(13) 0.6282(4) 0.134(3) Uani 1 4 d . . .
C24 C 0.5059(7) 0.0011(12) 0.6714(3) 0.118(3) Uani 1 4 d . . .
C25 C 0.3909(6) -0.0010(12) 0.6761(4) 0.115(3) Uani 1 4 d . . .
C26 C 0.3561(7) 0.1704(15) 0.6965(4) 0.126(3) Uani 1 4 d . . .
C27 C 0.3797(5) 0.1754(14) 0.7538(3) 0.110(2) Uani 1 4 d . . .
C28 C 0.3826(6) 0.3757(12) 0.7795(4) 0.106(3) Uani 1 4 d . . .
C29 C 0.4506(5) 0.5070(13) 0.7593(4) 0.107(2) Uani 1 4 d . . .
H3 H 0.63362 0.70622 0.93722 0.0732 Uiso 1 4 calc R . .
H4 H 0.55943 0.74991 0.84402 0.0776 Uiso 1 4 calc R . .
H6 H 0.67499 0.21331 0.96313 0.0551 Uiso 1 4 calc R . .
H7A H 0.79215 0.52135 0.97083 0.0635 Uiso 1 4 calc R . .
H7B H 0.79949 0.39231 1.02247 0.0635 Uiso 1 4 calc R . .
H8A H 0.82859 0.27195 0.9175 0.0770 Uiso 1 4 calc R . .
H8B H 0.912 0.31963 0.96416 0.0770 Uiso 1 4 calc R . .
H9A H 0.78419 0.03035 0.97185 0.0819 Uiso 1 4 calc R . .
H9B H 0.88515 0.00364 0.95324 0.0819 Uiso 1 4 calc R . .
H10A H 0.86306 0.14346 1.05669 0.0785 Uiso 1 4 calc R . .
H10B H 0.95963 0.08178 1.03758 0.0785 Uiso 1 4 calc R . .
H11A H 0.90104 -0.22539 1.03248 0.0862 Uiso 1 4 calc R . .
H11B H 0.91944 -0.14641 1.09246 0.0862 Uiso 1 4 calc R . .
H12A H 0.73684 -0.15256 1.03053 0.0901 Uiso 1 4 calc R . .
H12B H 0.77307 -0.30906 1.07213 0.0901 Uiso 1 4 calc R . .
H13A H 0.77485 0.0442 1.11429 0.0895 Uiso 1 4 calc R . .
H13B H 0.75792 -0.14082 1.14427 0.0895 Uiso 1 4 calc R . .
H14A H 0.60243 -0.15542 1.0951 0.0916 Uiso 1 4 calc R . .
H14B H 0.6168 0.01531 1.13432 0.0916 Uiso 1 4 calc R . .
H15A H 0.5331 0.08497 1.04827 0.0789 Uiso 1 4 calc R . .
H15B H 0.62448 0.03565 1.02143 0.0789 Uiso 1 4 calc R . .
H16A H 0.70576 0.27325 1.07582 0.0772 Uiso 1 4 calc R . .
H16B H 0.60667 0.33138 1.09233 0.0772 Uiso 1 4 calc R . .
H17A H 0.63234 0.5225 1.02385 0.0723 Uiso 1 4 calc R . .
H17B H 0.55249 0.38659 0.99801 0.0723 Uiso 1 4 calc R . .
H18 H 0.54814 0.30973 0.76924 0.0928 Uiso 1 4 calc R . .
H19A H 0.61275 0.67465 0.73843 0.0992 Uiso 1 4 calc R . .
H19B H 0.68946 0.52456 0.75939 0.0992 Uiso 1 4 calc R . .
H20A H 0.54815 0.44959 0.67118 0.1209 Uiso 1 4 calc R . .
H20B H 0.64394 0.54524 0.66099 0.1209 Uiso 1 4 calc R . .
H21A H 0.6497 0.22903 0.72002 0.1361 Uiso 1 4 calc R . .
H21B H 0.72857 0.3117 0.68835 0.1361 Uiso 1 4 calc R . .
H22A H 0.64692 0.21595 0.60488 0.1260 Uiso 1 4 calc R . .
H22B H 0.66584 0.04724 0.64448 0.1260 Uiso 1 4 calc R . .
H23A H 0.48743 0.22407 0.62677 0.1604 Uiso 1 4 calc R . .
H23B H 0.51093 0.04844 0.59348 0.1604 Uiso 1 4 calc R . .
H24A H 0.54076 0.04581 0.70571 0.1418 Uiso 1 4 calc R . .
H24B H 0.52728 -0.12339 0.66558 0.1418 Uiso 1 4 calc R . .
H25A H 0.35587 -0.0264 0.64001 0.1380 Uiso 1 4 calc R . .
H25B H 0.37775 -0.10029 0.70045 0.1380 Uiso 1 4 calc R . .
H26A H 0.38506 0.27403 0.68007 0.1516 Uiso 1 4 calc R . .
H26B H 0.28728 0.17854 0.68668 0.1516 Uiso 1 4 calc R . .
H27A H 0.44187 0.11855 0.76357 0.1324 Uiso 1 4 calc R . .
H27B H 0.33343 0.10241 0.77018 0.1324 Uiso 1 4 calc R . .
H28A H 0.31885 0.42795 0.77222 0.1272 Uiso 1 4 calc R . .
H28B H 0.39857 0.36488 0.81911 0.1272 Uiso 1 4 calc R . .
H29A H 0.43839 0.51525 0.7195 0.1287 Uiso 1 4 calc R . .
H29B H 0.4424 0.62849 0.77445 0.1287 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Se1 C1 1.843(5) yes . .
N2 C1 1.360(7) yes . .
N2 C3 1.387(6) yes . .
N2 C6 1.462(6) yes . .
N5 C1 1.355(6) yes . .
N5 C4 1.386(7) yes . .
N5 C18 1.487(8) yes . .
C3 C4 1.328(9) yes . .
C6 C7 1.531(7) yes . .
C6 C17 1.536(8) yes . .
C7 C8 1.523(8) yes . .
C8 C9 1.513(9) yes . .
C9 C10 1.510(8) yes . .
C10 C11 1.537(9) yes . .
C11 C12 1.532(9) yes . .
C12 C13 1.527(10) yes . .
C13 C14 1.545(9) yes . .
C14 C15 1.504(9) yes . .
C15 C16 1.517(9) yes . .
C16 C17 1.531(8) yes . .
C18 C19 1.700(10) yes . .
C18 C29 1.473(10) yes . .
C19 C20 1.499(11) yes . .
C20 C21 1.428(13) yes . .
C21 C22 1.563(12) yes . .
C22 C23 1.523(15) yes . .
C23 C24 1.422(14) yes . .
C24 C25 1.677(14) yes . .
C25 C26 1.482(14) yes . .
C26 C27 1.428(12) yes . .
C27 C28 1.616(13) yes . .
C28 C29 1.515(13) yes . .
C3 H3 0.950 no . .
C4 H4 0.950 no . .
C6 H6 1.000 no . .
C7 H7A 0.990 no . .
C7 H7B 0.990 no . .
C8 H8A 0.990 no . .
C8 H8B 0.990 no . .
C9 H9A 0.990 no . .
C9 H9B 0.990 no . .
C10 H10A 0.990 no . .
C10 H10B 0.990 no . .
C11 H11A 0.990 no . .
C11 H11B 0.990 no . .
C12 H12A 0.990 no . .
C12 H12B 0.990 no . .
C13 H13A 0.990 no . .
C13 H13B 0.990 no . .
C14 H14A 0.990 no . .
C14 H14B 0.990 no . .
C15 H15A 0.990 no . .
C15 H15B 0.990 no . .
C16 H16A 0.990 no . .
C16 H16B 0.990 no . .
C17 H17A 0.990 no . .
C17 H17B 0.990 no . .
C18 H18 1.000 no . .
C19 H19A 0.990 no . .
C19 H19B 0.990 no . .
C20 H20A 0.990 no . .
C20 H20B 0.990 no . .
C21 H21A 0.990 no . .
C21 H21B 0.990 no . .
C22 H22A 0.990 no . .
C22 H22B 0.990 no . .
C23 H23A 0.990 no . .
C23 H23B 0.990 no . .
C24 H24A 0.990 no . .
C24 H24B 0.990 no . .
C25 H25A 0.990 no . .
C25 H25B 0.990 no . .
C26 H26A 0.990 no . .
C26 H26B 0.990 no . .
C27 H27A 0.990 no . .
C27 H27B 0.990 no . .
C28 H28A 0.990 no . .
C28 H28B 0.990 no . .
C29 H29A 0.990 no . .
C29 H29B 0.990 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N2 C3 109.3(4) yes . . .
C1 N2 C6 125.2(4) yes . . .
C3 N2 C6 125.5(4) yes . . .
C1 N5 C4 109.7(4) yes . . .
C1 N5 C18 125.4(4) yes . . .
C4 N5 C18 124.5(4) yes . . .
Se1 C1 N2 126.8(4) yes . . .
Se1 C1 N5 127.4(4) yes . . .
N2 C1 N5 105.9(4) yes . . .
N2 C3 C4 107.8(5) yes . . .
N5 C4 C3 107.4(4) yes . . .
N2 C6 C7 110.3(4) yes . . .
N2 C6 C17 110.0(4) yes . . .
C7 C6 C17 113.4(4) yes . . .
C6 C7 C8 113.1(4) yes . . .
C7 C8 C9 115.4(5) yes . . .
C8 C9 C10 113.5(5) yes . . .
C9 C10 C11 113.9(5) yes . . .
C10 C11 C12 113.5(5) yes . . .
C11 C12 C13 114.3(5) yes . . .
C12 C13 C14 114.1(5) yes . . .
C13 C14 C15 114.5(6) yes . . .
C14 C15 C16 112.9(5) yes . . .
C15 C16 C17 113.9(5) yes . . .
C6 C17 C16 114.3(5) yes . . .
N5 C18 C19 109.3(5) yes . . .
N5 C18 C29 111.7(6) yes . . .
C19 C18 C29 111.7(6) yes . . .
C18 C19 C20 109.0(6) yes . . .
C19 C20 C21 110.7(7) yes . . .
C20 C21 C22 117.4(7) yes . . .
C21 C22 C23 115.9(8) yes . . .
C22 C23 C24 107.9(8) yes . . .
C23 C24 C25 111.2(8) yes . . .
C24 C25 C26 113.6(7) yes . . .
C25 C26 C27 108.8(8) yes . . .
C26 C27 C28 114.4(8) yes . . .
C27 C28 C29 116.1(8) yes . . .
C18 C29 C28 108.7(7) yes . . .
N2 C3 H3 126.119 no . . .
C4 C3 H3 126.116 no . . .
N5 C4 H4 126.302 no . . .
C3 C4 H4 126.287 no . . .
N2 C6 H6 107.658 no . . .
C7 C6 H6 107.672 no . . .
C17 C6 H6 107.660 no . . .
C6 C7 H7A 108.976 no . . .
C6 C7 H7B 108.974 no . . .
C8 C7 H7A 108.965 no . . .
C8 C7 H7B 108.963 no . . .
H7A C7 H7B 107.776 no . . .
C7 C8 H8A 108.434 no . . .
C7 C8 H8B 108.444 no . . .
C9 C8 H8A 108.428 no . . .
C9 C8 H8B 108.444 no . . .
H8A C8 H8B 107.465 no . . .
C8 C9 H9A 108.878 no . . .
C8 C9 H9B 108.877 no . . .
C10 C9 H9A 108.857 no . . .
C10 C9 H9B 108.868 no . . .
H9A C9 H9B 107.722 no . . .
C9 C10 H10A 108.759 no . . .
C9 C10 H10B 108.750 no . . .
C11 C10 H10A 108.767 no . . .
C11 C10 H10B 108.770 no . . .
H10A C10 H10B 107.667 no . . .
C10 C11 H11A 108.867 no . . .
C10 C11 H11B 108.860 no . . .
C12 C11 H11A 108.870 no . . .
C12 C11 H11B 108.854 no . . .
H11A C11 H11B 107.714 no . . .
C11 C12 H12A 108.695 no . . .
C11 C12 H12B 108.692 no . . .
C13 C12 H12A 108.684 no . . .
C13 C12 H12B 108.686 no . . .
H12A C12 H12B 107.617 no . . .
C12 C13 H13A 108.727 no . . .
C12 C13 H13B 108.723 no . . .
C14 C13 H13A 108.717 no . . .
C14 C13 H13B 108.724 no . . .
H13A C13 H13B 107.616 no . . .
C13 C14 H14A 108.628 no . . .
C13 C14 H14B 108.632 no . . .
C15 C14 H14A 108.632 no . . .
C15 C14 H14B 108.631 no . . .
H14A C14 H14B 107.580 no . . .
C14 C15 H15A 109.022 no . . .
C14 C15 H15B 109.012 no . . .
C16 C15 H15A 109.005 no . . .
C16 C15 H15B 109.011 no . . .
H15A C15 H15B 107.786 no . . .
C15 C16 H16A 108.769 no . . .
C15 C16 H16B 108.783 no . . .
C17 C16 H16A 108.766 no . . .
C17 C16 H16B 108.778 no . . .
H16A C16 H16B 107.674 no . . .
C6 C17 H17A 108.673 no . . .
C6 C17 H17B 108.684 no . . .
C16 C17 H17A 108.677 no . . .
C16 C17 H17B 108.676 no . . .
H17A C17 H17B 107.605 no . . .
N5 C18 H18 108.002 no . . .
C19 C18 H18 107.990 no . . .
C29 C18 H18 107.997 no . . .
C18 C19 H19A 109.877 no . . .
C18 C19 H19B 109.868 no . . .
C20 C19 H19A 109.876 no . . .
C20 C19 H19B 109.884 no . . .
H19A C19 H19B 108.293 no . . .
C19 C20 H20A 109.517 no . . .
C19 C20 H20B 109.506 no . . .
C21 C20 H20A 109.507 no . . .
C21 C20 H20B 109.505 no . . .
H20A C20 H20B 108.061 no . . .
C20 C21 H21A 107.949 no . . .
C20 C21 H21B 107.953 no . . .
C22 C21 H21A 107.951 no . . .
C22 C21 H21B 107.948 no . . .
H21A C21 H21B 107.231 no . . .
C21 C22 H22A 108.318 no . . .
C21 C22 H22B 108.324 no . . .
C23 C22 H22A 108.318 no . . .
C23 C22 H22B 108.308 no . . .
H22A C22 H22B 107.401 no . . .
C22 C23 H23A 110.125 no . . .
C22 C23 H23B 110.124 no . . .
C24 C23 H23A 110.133 no . . .
C24 C23 H23B 110.136 no . . .
H23A C23 H23B 108.441 no . . .
C23 C24 H24A 109.389 no . . .
C23 C24 H24B 109.394 no . . .
C25 C24 H24A 109.383 no . . .
C25 C24 H24B 109.385 no . . .
H24A C24 H24B 108.004 no . . .
C24 C25 H25A 108.851 no . . .
C24 C25 H25B 108.856 no . . .
C26 C25 H25A 108.857 no . . .
C26 C25 H25B 108.861 no . . .
H25A C25 H25B 107.703 no . . .
C25 C26 H26A 109.921 no . . .
C25 C26 H26B 109.923 no . . .
C27 C26 H26A 109.913 no . . .
C27 C26 H26B 109.913 no . . .
H26A C26 H26B 108.319 no . . .
C26 C27 H27A 108.669 no . . .
C26 C27 H27B 108.660 no . . .
C28 C27 H27A 108.666 no . . .
C28 C27 H27B 108.661 no . . .
H27A C27 H27B 107.601 no . . .
C27 C28 H28A 108.265 no . . .
C27 C28 H28B 108.252 no . . .
C29 C28 H28A 108.255 no . . .
C29 C28 H28B 108.249 no . . .
H28A C28 H28B 107.370 no . . .
C18 C29 H29A 109.953 no . . .
C18 C29 H29B 109.958 no . . .
C28 C29 H29A 109.953 no . . .
C28 C29 H29B 109.956 no . . .
H29A C29 H29B 108.344 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N2 C3 C4 1.1(6) no . . . .
C3 N2 C1 Se1 178.3(4) no . . . .
C3 N2 C1 N5 -0.8(5) no . . . .
C1 N2 C6 C7 110.7(5) no . . . .
C1 N2 C6 C17 -123.6(5) no . . . .
C6 N2 C1 Se1 -4.2(7) no . . . .
C6 N2 C1 N5 176.7(4) no . . . .
C3 N2 C6 C7 -72.3(6) no . . . .
C3 N2 C6 C17 53.5(6) no . . . .
C6 N2 C3 C4 -176.4(4) no . . . .
C1 N5 C4 C3 0.4(6) no . . . .
C4 N5 C1 Se1 -178.9(4) no . . . .
C4 N5 C1 N2 0.2(6) no . . . .
C1 N5 C18 C19 -107.6(5) no . . . .
C1 N5 C18 C29 128.3(5) no . . . .
C18 N5 C1 Se1 -6.0(8) no . . . .
C18 N5 C1 N2 173.1(5) no . . . .
C4 N5 C18 C19 64.3(7) no . . . .
C4 N5 C18 C29 -59.8(7) no . . . .
C18 N5 C4 C3 -172.5(5) no . . . .
N2 C3 C4 N5 -0.9(7) no . . . .
N2 C6 C7 C8 -86.5(5) no . . . .
N2 C6 C17 C16 164.6(3) no . . . .
C7 C6 C17 C16 -71.4(5) no . . . .
C17 C6 C7 C8 149.7(4) no . . . .
C6 C7 C8 C9 -65.2(5) no . . . .
C7 C8 C9 C10 -67.5(6) no . . . .
C8 C9 C10 C11 170.4(4) no . . . .
C9 C10 C11 C12 -69.8(7) no . . . .
C10 C11 C12 C13 -69.9(7) no . . . .
C11 C12 C13 C14 150.7(5) no . . . .
C12 C13 C14 C15 -66.0(8) no . . . .
C13 C14 C15 C16 -66.8(7) no . . . .
C14 C15 C16 C17 170.1(5) no . . . .
C15 C16 C17 C6 -69.9(6) no . . . .
N5 C18 C19 C20 160.6(4) no . . . .
N5 C18 C29 C28 -74.0(7) no . . . .
C19 C18 C29 C28 163.2(5) no . . . .
C29 C18 C19 C20 -75.3(7) no . . . .
C18 C19 C20 C21 -77.8(7) no . . . .
C19 C20 C21 C22 159.6(6) no . . . .
C20 C21 C22 C23 -57.5(10) no . . . .
C21 C22 C23 C24 -69.9(9) no . . . .
C22 C23 C24 C25 160.7(6) no . . . .
C23 C24 C25 C26 -71.6(9) no . . . .
C24 C25 C26 C27 -79.3(9) no . . . .
C25 C26 C27 C28 158.1(7) no . . . .
C26 C27 C28 C29 -58.8(9) no . . . .
C27 C28 C29 C18 -65.5(9) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Se1 C6 3.319(5) no . .
Se1 C18 3.348(6) no . .
N2 C8 3.247(7) no . .
N5 C6 3.585(6) no . .
N5 C28 3.028(10) no . .
C1 C7 3.483(7) no . .
C1 C17 3.574(8) no . .
C1 C19 3.591(8) no . .
C1 C29 3.592(9) no . .
C3 C7 3.189(7) no . .
C3 C17 3.036(8) no . .
C4 C19 3.213(10) no . .
C4 C29 3.088(10) no . .
C6 C9 3.150(8) no . .
C6 C15 3.204(8) no . .
C7 C10 3.164(8) no . .
C7 C16 3.220(8) no . .
C9 C12 3.188(9) no . .
C10 C13 3.204(9) no . .
C12 C15 3.173(9) no . .
C13 C16 3.141(9) no . .
C18 C21 3.164(12) no . .
C18 C27 3.107(11) no . .
C20 C23 3.154(13) no . .
C20 C29 3.220(13) no . .
C21 C24 3.080(13) no . .
C23 C26 3.196(16) no . .
C24 C27 3.201(13) no . .
C26 C29 3.157(14) no . .
Se1 C4 3.490(5) no . 1_545
C4 Se1 3.490(5) no . 1_565
Se1 H6 2.7645 no . .
Se1 H8A 3.3444 no . .
Se1 H9A 3.4436 no . .
Se1 H18 2.8049 no . .
Se1 H27A 3.2982 no . .
N2 H4 3.1157 no . .
N2 H7A 2.4929 no . .
N2 H7B 3.2546 no . .
N2 H8A 2.9680 no . .
N2 H17A 2.7538 no . .
N2 H17B 2.5341 no . .
N5 H3 3.1098 no . .
N5 H19A 2.9544 no . .
N5 H19B 2.6894 no . .
N5 H27A 3.5849 no . .
N5 H28B 2.6579 no . .
N5 H29A 3.2922 no . .
N5 H29B 2.5639 no . .
C1 H3 3.1541 no . .
C1 H4 3.1546 no . .
C1 H6 2.5570 no . .
C1 H7A 3.5942 no . .
C1 H8A 3.2118 no . .
C1 H17B 3.4341 no . .
C1 H18 2.5913 no . .
C1 H19B 3.4028 no . .
C1 H28B 3.1834 no . .
C3 H6 3.3034 no . .
C3 H7A 2.7989 no . .
C3 H17A 2.8962 no . .
C3 H17B 3.0313 no . .
C4 H18 3.3230 no . .
C4 H19A 3.1510 no . .
C4 H19B 3.2539 no . .
C4 H28B 3.3662 no . .
C4 H29B 2.7214 no . .
C6 H3 2.8278 no . .
C6 H8A 2.7094 no . .
C6 H8B 3.3803 no . .
C6 H9A 2.7890 no . .
C6 H10A 3.5463 no . .
C6 H15B 2.8239 no . .
C6 H16A 2.7148 no . .
C6 H16B 3.4020 no . .
C7 H3 3.2429 no . .
C7 H9A 2.7266 no . .
C7 H9B 3.3911 no . .
C7 H10A 2.7729 no . .
C7 H10B 3.5866 no . .
C7 H16A 2.8599 no . .
C7 H17A 2.6876 no . .
C7 H17B 3.3884 no . .
C8 H6 2.5468 no . .
C8 H10A 2.6468 no . .
C8 H10B 2.7826 no . .
C9 H6 2.6826 no . .
C9 H7A 3.3921 no . .
C9 H7B 2.7446 no . .
C9 H11A 2.6980 no . .
C9 H11B 3.3791 no . .
C9 H12A 2.8214 no . .
C9 H15B 3.5841 no . .
C10 H6 3.5782 no . .
C10 H7B 2.8323 no . .
C10 H8A 3.3557 no . .
C10 H8B 2.6794 no . .
C10 H12A 2.7003 no . .
C10 H12B 3.3944 no . .
C10 H13A 2.7856 no . .
C10 H16A 3.4127 no . .
C11 H9A 2.6729 no . .
C11 H9B 2.8093 no . .
C11 H13A 2.5813 no . .
C11 H13B 2.9749 no . .
C12 H9A 2.8038 no . .
C12 H10A 2.7033 no . .
C12 H10B 3.3944 no . .
C12 H14A 2.7429 no . .
C12 H14B 3.4043 no . .
C12 H15B 2.8149 no . .
C12 H16A 3.5285 no . .
C13 H10A 2.8376 no . .
C13 H11A 3.3941 no . .
C13 H11B 2.7090 no . .
C13 H15A 3.3982 no . .
C13 H15B 2.7228 no . .
C13 H16A 2.7356 no . .
C13 H16B 3.5713 no . .
C14 H12A 2.5855 no . .
C14 H12B 2.9821 no . .
C14 H16A 2.6347 no . .
C14 H16B 2.7752 no . .
C15 H6 2.8056 no . .
C15 H9A 3.5710 no . .
C15 H12A 2.7381 no . .
C15 H13A 2.7359 no . .
C15 H13B 3.3883 no . .
C15 H17A 3.3790 no . .
C15 H17B 2.6937 no . .
C16 H6 2.6765 no . .
C16 H7B 2.8072 no . .
C16 H10A 3.4203 no . .
C16 H13A 2.7944 no . .
C16 H14A 3.3524 no . .
C16 H14B 2.6707 no . .
C17 H3 3.0084 no . .
C17 H7A 2.9807 no . .
C17 H7B 2.5704 no . .
C17 H15A 2.8158 no . .
C17 H15B 2.6760 no . .
C18 H4 2.8308 no . .
C18 H20A 2.6352 no . .
C18 H20B 3.4612 no . .
C18 H21A 2.6942 no . .
C18 H24A 3.4254 no . .
C18 H26A 3.3549 no . .
C18 H27A 2.8314 no . .
C18 H28A 3.2726 no . .
C18 H28B 2.5800 no . .
C19 H4 3.2509 no . .
C19 H21A 2.4241 no . .
C19 H21B 2.7271 no . .
C19 H29A 2.6756 no . .
C19 H29B 2.9370 no . .
C20 H18 2.6819 no . .
C20 H22A 2.8057 no . .
C20 H22B 3.3595 no . .
C20 H23A 2.8197 no . .
C20 H24A 3.3372 no . .
C20 H26A 3.5878 no . .
C20 H29A 2.8239 no . .
C21 H18 2.8010 no . .
C21 H19A 3.2391 no . .
C21 H19B 2.5099 no . .
C21 H23A 2.7670 no . .
C21 H23B 3.4499 no . .
C21 H24A 2.5953 no . .
C22 H20A 2.6304 no . .
C22 H20B 2.9108 no . .
C22 H24A 2.4108 no . .
C22 H24B 2.7112 no . .
C23 H20A 2.7188 no . .
C23 H21A 2.8424 no . .
C23 H21B 3.4300 no . .
C23 H25A 2.7098 no . .
C23 H25B 3.3711 no . .
C23 H26A 2.8173 no . .
C24 H18 3.3450 no . .
C24 H20A 3.3803 no . .
C24 H21A 2.8172 no . .
C24 H22A 3.2191 no . .
C24 H22B 2.5110 no . .
C24 H26A 2.6971 no . .
C24 H26B 3.4819 no . .
C24 H27A 2.7398 no . .
C25 H23A 2.5908 no . .
C25 H23B 2.8943 no . .
C25 H27A 2.3828 no . .
C25 H27B 2.7108 no . .
C26 H18 3.2646 no . .
C26 H20A 3.5804 no . .
C26 H23A 2.7722 no . .
C26 H24A 2.7957 no . .
C26 H24B 3.4563 no . .
C26 H28A 2.7930 no . .
C26 H28B 3.3694 no . .
C26 H29A 2.8435 no . .
C27 H18 2.6023 no . .
C27 H24A 2.9186 no . .
C27 H25A 3.1933 no . .
C27 H25B 2.4394 no . .
C27 H29A 2.8277 no . .
C27 H29B 3.4979 no . .
C28 H18 2.4821 no . .
C28 H26A 2.6042 no . .
C28 H26B 2.9228 no . .
C29 H4 3.0471 no . .
C29 H19A 2.7590 no . .
C29 H19B 3.4439 no . .
C29 H20A 2.8056 no . .
C29 H26A 2.7009 no . .
C29 H27A 2.8851 no . .
C29 H27B 3.4702 no . .
H3 H4 2.4504 no . .
H3 H7A 2.6974 no . .
H3 H17A 2.5623 no . .
H3 H17B 3.1274 no . .
H4 H19A 2.9047 no . .
H4 H19B 3.4451 no . .
H4 H29B 2.4250 no . .
H6 H7A 2.8305 no . .
H6 H7B 2.5405 no . .
H6 H8A 2.6607 no . .
H6 H8B 3.5008 no . .
H6 H9A 2.0659 no . .
H6 H9B 3.4421 no . .
H6 H10A 3.3698 no . .
H6 H12A 3.2533 no . .
H6 H15A 3.2883 no . .
H6 H15B 2.1639 no . .
H6 H16A 2.8291 no . .
H6 H17A 2.8627 no . .
H6 H17B 2.4387 no . .
H7A H8A 2.3804 no . .
H7A H8B 2.3073 no . .
H7A H10A 3.5927 no . .
H7A H16A 3.5675 no . .
H7A H17A 2.8099 no . .
H7B H8A 2.8587 no . .
H7B H8B 2.3859 no . .
H7B H9A 2.9626 no . .
H7B H10A 2.1819 no . .
H7B H10B 3.2444 no . .
H7B H13A 3.5054 no . .
H7B H16A 2.2084 no . .
H7B H16B 3.5076 no . .
H7B H17A 2.5988 no . .
H7B H17B 3.5273 no . .
H8A H9A 2.3884 no . .
H8A H9B 2.2849 no . .
H8A H10A 3.5794 no . .
H8B H9A 2.8501 no . .
H8B H9B 2.3839 no . .
H8B H10A 2.8302 no . .
H8B H10B 2.5711 no . .
H9A H10A 2.4169 no . .
H9A H10B 2.8463 no . .
H9A H11A 2.8340 no . .
H9A H12A 2.1757 no . .
H9A H12B 3.5726 no . .
H9A H13A 3.5866 no . .
H9A H15B 2.7594 no . .
H9A H16A 3.4772 no . .
H9B H10A 2.8464 no . .
H9B H10B 2.3069 no . .
H9B H11A 2.5967 no . .
H9B H12A 3.2826 no . .
H10A H11A 2.8695 no . .
H10A H11B 2.4248 no . .
H10A H12A 2.8679 no . .
H10A H13A 2.1759 no . .
H10A H13B 3.5278 no . .
H10A H15B 3.5215 no . .
H10A H16A 2.5664 no . .
H10B H11A 2.4258 no . .
H10B H11B 2.3022 no . .
H10B H13A 3.4992 no . .
H11A H12A 2.4202 no . .
H11A H12B 2.2951 no . .
H11A H13A 3.5365 no . .
H11B H12A 2.8651 no . .
H11B H12B 2.4219 no . .
H11B H13A 2.6353 no . .
H11B H13B 2.8145 no . .
H12A H13A 2.5508 no . .
H12A H13B 2.8220 no . .
H12A H14A 2.6862 no . .
H12A H14B 3.5372 no . .
H12A H15A 3.5026 no . .
H12A H15B 2.1255 no . .
H12A H16A 3.4041 no . .
H12B H13A 2.8221 no . .
H12B H13B 2.2292 no . .
H12B H14A 2.8384 no . .
H12B H15B 3.4611 no . .
H13A H14A 2.8747 no . .
H13A H14B 2.4069 no . .
H13A H15B 2.9529 no . .
H13A H16A 2.1304 no . .
H13A H16B 3.2156 no . .
H13B H14A 2.4061 no . .
H13B H14B 2.3230 no . .
H13B H16A 3.5453 no . .
H14A H15A 2.2862 no . .
H14A H15B 2.3803 no . .
H14A H16A 3.5698 no . .
H14B H15A 2.3764 no . .
H14B H15B 2.8461 no . .
H14B H16A 2.8204 no . .
H14B H16B 2.5639 no . .
H15A H16A 2.8533 no . .
H15A H16B 2.3143 no . .
H15A H17B 2.5991 no . .
H15B H16A 2.4270 no . .
H15B H16B 2.8538 no . .
H15B H17B 2.8322 no . .
H16A H17A 2.4183 no . .
H16A H17B 2.8630 no . .
H16B H17A 2.2921 no . .
H16B H17B 2.4173 no . .
H18 H19A 2.9959 no . .
H18 H19B 2.6228 no . .
H18 H20A 2.6638 no . .
H18 H21A 2.1232 no . .
H18 H21B 3.5059 no . .
H18 H24A 2.5140 no . .
H18 H26A 3.0224 no . .
H18 H27A 2.0768 no . .
H18 H27B 3.4568 no . .
H18 H28A 3.4280 no . .
H18 H28B 2.6650 no . .
H18 H29A 2.4150 no . .
H18 H29B 2.8241 no . .
H19A H20A 2.4604 no . .
H19A H20B 2.2617 no . .
H19A H21A 3.3876 no . .
H19A H21B 3.4879 no . .
H19A H29A 2.7576 no . .
H19A H29B 2.7489 no . .
H19B H20A 2.8454 no . .
H19B H20B 2.4647 no . .
H19B H21A 2.4381 no . .
H19B H21B 2.4983 no . .
H20A H21A 2.4121 no . .
H20A H21B 2.7712 no . .
H20A H22A 2.9021 no . .
H20A H22B 3.5394 no . .
H20A H23A 2.1282 no . .
H20A H23B 3.5534 no . .
H20A H24A 3.1214 no . .
H20A H26A 2.7214 no . .
H20A H29A 2.1729 no . .
H20A H29B 3.4400 no . .
H20B H21A 2.7659 no . .
H20B H21B 2.1735 no . .
H20B H22A 2.8193 no . .
H20B H23A 3.3102 no . .
H20B H29A 3.4852 no . .
H21A H22A 2.8776 no . .
H21A H22B 2.3587 no . .
H21A H23A 3.0691 no . .
H21A H24A 2.0694 no . .
H21A H24B 3.3369 no . .
H21A H27A 3.4226 no . .
H21B H22A 2.3618 no . .
H21B H22B 2.3652 no . .
H21B H24A 3.4228 no . .
H22A H23A 2.4345 no . .
H22A H23B 2.3040 no . .
H22A H24A 3.3690 no . .
H22A H24B 3.5102 no . .
H22B H23A 2.8651 no . .
H22B H23B 2.4146 no . .
H22B H24A 2.5197 no . .
H22B H24B 2.4802 no . .
H23A H24A 2.4132 no . .
H23A H24B 2.7848 no . .
H23A H25A 2.7057 no . .
H23A H25B 3.5319 no . .
H23A H26A 2.1514 no . .
H23A H26B 3.4433 no . .
H23A H29A 3.3153 no . .
H23B H24A 2.7824 no . .
H23B H24B 2.1947 no . .
H23B H25A 2.7137 no . .
H23B H26A 3.4429 no . .
H24A H25A 2.9810 no . .
H24A H25B 2.5730 no . .
H24A H26A 2.8128 no . .
H24A H27A 2.2317 no . .
H24B H25A 2.5675 no . .
H24B H25B 2.4382 no . .
H24B H27A 3.4012 no . .
H25A H26A 2.4549 no . .
H25A H26B 2.2280 no . .
H25A H27A 3.3469 no . .
H25A H27B 3.4516 no . .
H25B H26A 2.8260 no . .
H25B H26B 2.4428 no . .
H25B H27A 2.3624 no . .
H25B H27B 2.4525 no . .
H26A H27A 2.4283 no . .
H26A H27B 2.7775 no . .
H26A H28A 2.8513 no . .
H26A H28B 3.5229 no . .
H26A H29A 2.1341 no . .
H26A H29B 3.5541 no . .
H26B H27A 2.7727 no . .
H26B H27B 2.1786 no . .
H26B H28A 2.8180 no . .
H26B H29A 3.3399 no . .
H27A H28A 2.9246 no . .
H27A H28B 2.4274 no . .
H27A H29A 3.1388 no . .
H27B H28A 2.4236 no . .
H27B H28B 2.4190 no . .
H28A H29A 2.3970 no . .
H28A H29B 2.3139 no . .
H28B H29A 2.8592 no . .
H28B H29B 2.3790 no . .
Se1 H3 3.5324 no . 1_545
Se1 H4 2.7781 no . 1_545
Se1 H20B 3.4381 no . 2_646
Se1 H21B 3.3158 no . 2_646
N2 H22B 3.4897 no . 2_656
C1 H22B 3.5905 no . 2_656
C3 H15A 3.3969 no . 3_667
C3 H16B 3.2895 no . 3_667
C3 H22A 3.5046 no . 2_656
C3 H22B 3.5743 no . 2_656
C4 H16B 3.1058 no . 3_667
C4 H21B 3.3999 no . 2_656
C7 H11A 3.4274 no . 1_565
C7 H12B 3.1422 no . 1_565
C7 H22A 3.4744 no . 2_656
C7 H22B 3.5489 no . 2_656
C8 H20B 3.4110 no . 2_646
C8 H22B 3.2492 no . 2_656
C8 H23B 3.2706 no . 2_656
C9 H10B 3.0590 no . 3_757
C9 H20B 3.4580 no . 2_646
C9 H22A 3.3658 no . 2_646
C10 H9B 3.2143 no . 3_757
C10 H10B 3.1465 no . 3_757
C10 H23A 3.0100 no . 4_555
C11 H7A 3.4622 no . 1_545
C11 H8B 3.4104 no . 3_757
C11 H9B 3.5741 no . 3_757
C11 H10B 3.5591 no . 3_757
C11 H25A 3.3005 no . 4_545
C12 H7A 3.2626 no . 1_545
C12 H7B 3.3806 no . 1_545
C12 H17A 3.1259 no . 1_545
C12 H25A 3.0033 no . 4_545
C13 H25A 3.4246 no . 4_545
C13 H26A 3.3538 no . 4_555
C13 H26B 3.5092 no . 4_555
C13 H27B 3.3292 no . 3_657
C13 H28B 3.5897 no . 3_657
C14 H27B 3.2265 no . 3_657
C14 H28B 3.2176 no . 3_657
C15 H15A 3.2573 no . 3_657
C16 H26B 3.5318 no . 4_555
C17 H12B 3.3136 no . 1_565
C17 H17B 2.9399 no . 3_667
C19 H21A 3.5391 no . 2_656
C19 H21B 3.2449 no . 2_656
C19 H24B 3.3029 no . 1_565
C20 H9B 3.4803 no . 2_656
C20 H24B 3.3284 no . 1_565
C21 H19B 3.1035 no . 2_646
C22 H7A 3.2571 no . 2_646
C22 H8A 3.2904 no . 2_646
C22 H8B 3.5884 no . 2_646
C22 H9B 3.4074 no . 2_656
C22 H19B 3.5438 no . 2_646
C23 H8A 3.5717 no . 2_646
C23 H8B 3.3829 no . 2_646
C23 H10A 3.2888 no . 4_454
C23 H10B 3.2538 no . 4_454
C24 H11B 3.4200 no . 4_444
C24 H19A 3.2141 no . 1_545
C25 H11B 3.4081 no . 4_444
C25 H12B 3.2283 no . 4_444
C25 H13B 3.3067 no . 4_444
C25 H28A 3.4850 no . 2_546
C26 H13A 3.0691 no . 4_454
C26 H16A 3.4922 no . 4_454
C26 H28A 3.2763 no . 2_546
C27 H13B 3.4473 no . 3_657
C27 H14B 3.1307 no . 3_657
C27 H28A 3.3856 no . 2_546
C28 H13B 3.4389 no . 3_657
C28 H14A 3.5183 no . 3_657
C28 H26B 3.5085 no . 2_556
C29 H25B 3.3650 no . 1_565
H3 Se1 3.5324 no . 1_565
H3 H9A 3.2735 no . 1_565
H3 H12A 2.7946 no . 1_565
H3 H15A 2.9214 no . 3_667
H3 H15B 3.2400 no . 1_565
H3 H16B 3.4507 no . 3_667
H3 H17B 3.3877 no . 3_667
H3 H22A 3.4671 no . 2_656
H4 Se1 2.7781 no . 1_565
H4 H14B 3.1850 no . 3_667
H4 H15A 3.3943 no . 3_667
H4 H16B 3.1092 no . 3_667
H4 H21B 3.2969 no . 2_656
H7A C11 3.4622 no . 1_565
H7A C12 3.2626 no . 1_565
H7A C22 3.2571 no . 2_656
H7A H11A 2.7756 no . 1_565
H7A H12A 3.0060 no . 1_565
H7A H12B 2.8761 no . 1_565
H7A H22A 2.6259 no . 2_656
H7A H22B 3.0341 no . 2_656
H7A H23B 3.4533 no . 2_656
H7B C12 3.3806 no . 1_565
H7B H11A 3.1835 no . 1_565
H7B H12A 3.5056 no . 1_565
H7B H12B 2.5922 no . 1_565
H7B H23A 3.5992 no . 4_555
H7B H23B 3.3389 no . 4_555
H7B H25A 3.1057 no . 4_555
H8A C22 3.2904 no . 2_656
H8A C23 3.5717 no . 2_656
H8A H20B 2.6554 no . 2_646
H8A H22A 3.3654 no . 2_656
H8A H22B 2.5711 no . 2_656
H8A H23B 3.1297 no . 2_656
H8A H24B 3.2272 no . 2_656
H8B C11 3.4104 no . 3_757
H8B C22 3.5884 no . 2_656
H8B C23 3.3829 no . 2_656
H8B H10B 3.5070 no . 3_757
H8B H11A 2.7726 no . 3_757
H8B H11B 3.2393 no . 3_757
H8B H22A 3.4549 no . 2_656
H8B H22B 3.2652 no . 2_656
H8B H23B 2.5745 no . 2_656
H8B H23B 3.4926 no . 4_555
H8B H24B 3.5014 no . 2_656
H9A H3 3.2735 no . 1_545
H9A H22A 3.2595 no . 2_646
H9B C10 3.2143 no . 3_757
H9B C11 3.5741 no . 3_757
H9B C20 3.4803 no . 2_646
H9B C22 3.4074 no . 2_646
H9B H10B 2.3051 no . 3_757
H9B H11A 3.4664 no . 3_757
H9B H11B 3.3515 no . 3_757
H9B H20A 3.4051 no . 2_646
H9B H20B 2.8484 no . 2_646
H9B H22A 2.5872 no . 2_646
H9B H23A 3.5606 no . 2_646
H10A C23 3.2888 no . 4_555
H10A H23A 2.5280 no . 4_555
H10A H23B 3.1727 no . 4_555
H10A H25A 3.5321 no . 4_555
H10A H26A 3.1207 no . 4_555
H10B C9 3.0590 no . 3_757
H10B C10 3.1465 no . 3_757
H10B C11 3.5591 no . 3_757
H10B C23 3.2538 no . 4_555
H10B H8B 3.5070 no . 3_757
H10B H9B 2.3051 no . 3_757
H10B H10B 2.6378 no . 3_757
H10B H11A 3.0327 no . 3_757
H10B H20A 3.4192 no . 4_555
H10B H22A 3.3349 no . 4_555
H10B H23A 2.6398 no . 4_555
H10B H23B 3.1201 no . 4_555
H11A C7 3.4274 no . 1_545
H11A H7A 2.7756 no . 1_545
H11A H7B 3.1835 no . 1_545
H11A H8B 2.7726 no . 3_757
H11A H9B 3.4664 no . 3_757
H11A H10B 3.0327 no . 3_757
H11A H22A 3.4397 no . 2_646
H11A H23B 3.1481 no . 4_545
H11A H25A 3.3953 no . 4_545
H11B C24 3.4200 no . 4_545
H11B C25 3.4081 no . 4_545
H11B H8B 3.2393 no . 3_757
H11B H9B 3.3515 no . 3_757
H11B H20A 2.9066 no . 4_555
H11B H20B 3.5279 no . 4_555
H11B H23A 3.3570 no . 4_555
H11B H23B 3.2575 no . 4_545
H11B H24B 2.8100 no . 4_545
H11B H25A 2.9044 no . 4_545
H11B H25B 3.4106 no . 4_545
H11B H29A 3.2997 no . 4_555
H12A H3 2.7946 no . 1_545
H12A H7A 3.0060 no . 1_545
H12A H7B 3.5056 no . 1_545
H12A H17A 2.8334 no . 1_545
H12B C7 3.1422 no . 1_545
H12B C17 3.3136 no . 1_545
H12B C25 3.2283 no . 4_545
H12B H7A 2.8761 no . 1_545
H12B H7B 2.5922 no . 1_545
H12B H16A 3.2498 no . 1_545
H12B H17A 2.5415 no . 1_545
H12B H25A 2.2895 no . 4_545
H12B H25B 3.4223 no . 4_545
H13A C26 3.0691 no . 4_555
H13A H23A 3.4879 no . 4_555
H13A H26A 2.5162 no . 4_555
H13A H26B 2.7293 no . 4_555
H13A H29A 3.3136 no . 4_555
H13B C25 3.3067 no . 4_545
H13B C27 3.4473 no . 3_657
H13B C28 3.4389 no . 3_657
H13B H25A 2.8512 no . 4_545
H13B H25B 2.8242 no . 4_545
H13B H26A 3.3320 no . 4_555
H13B H26B 3.5954 no . 4_555
H13B H27B 2.6769 no . 3_657
H13B H28A 3.2791 no . 3_657
H13B H28A 3.5698 no . 4_555
H13B H28B 3.0407 no . 3_657
H13B H29A 3.1355 no . 4_555
H14A C28 3.5183 no . 3_657
H14A H17A 3.0455 no . 1_545
H14A H17B 3.4532 no . 3_657
H14A H27B 3.3942 no . 3_657
H14A H28B 2.6511 no . 3_657
H14B C27 3.1307 no . 3_657
H14B H4 3.1850 no . 3_667
H14B H26B 3.4669 no . 4_555
H14B H27A 2.9695 no . 3_657
H14B H27B 2.5530 no . 3_657
H14B H28B 3.0694 no . 3_657
H15A C3 3.3969 no . 3_667
H15A C15 3.2573 no . 3_657
H15A H3 2.9214 no . 3_667
H15A H4 3.3943 no . 3_667
H15A H15A 2.7753 no . 3_657
H15A H15B 2.8129 no . 3_657
H15B H3 3.2400 no . 1_545
H15B H15A 2.8129 no . 3_657
H16A C26 3.4922 no . 4_555
H16A H12B 3.2498 no . 1_565
H16A H25A 3.1350 no . 4_555
H16A H26A 3.4289 no . 4_555
H16A H26B 2.8830 no . 4_555
H16B C3 3.2895 no . 3_667
H16B C4 3.1058 no . 3_667
H16B H3 3.4507 no . 3_667
H16B H4 3.1092 no . 3_667
H16B H26B 3.2664 no . 4_555
H16B H28B 3.1674 no . 3_667
H16B H29B 3.5135 no . 3_667
H17A C12 3.1259 no . 1_565
H17A H12A 2.8334 no . 1_565
H17A H12B 2.5415 no . 1_565
H17A H14A 3.0455 no . 1_565
H17A H17B 2.7285 no . 3_667
H17B C17 2.9399 no . 3_667
H17B H3 3.3877 no . 3_667
H17B H14A 3.4532 no . 3_657
H17B H17A 2.7285 no . 3_667
H17B H17B 2.2728 no . 3_667
H19A C24 3.2141 no . 1_565
H19A H21A 3.4614 no . 2_656
H19A H21B 2.9102 no . 2_656
H19A H24A 3.0141 no . 1_565
H19A H24B 2.5430 no . 1_565
H19B C21 3.1035 no . 2_656
H19B C22 3.5438 no . 2_656
H19B H21A 2.7578 no . 2_656
H19B H21B 2.6858 no . 2_656
H19B H22B 2.9646 no . 2_656
H20A H9B 3.4051 no . 2_656
H20A H10B 3.4192 no . 4_454
H20A H11B 2.9066 no . 4_454
H20A H24B 3.1811 no . 1_565
H20B Se1 3.4381 no . 2_656
H20B C8 3.4110 no . 2_656
H20B C9 3.4580 no . 2_656
H20B H8A 2.6554 no . 2_656
H20B H9B 2.8484 no . 2_656
H20B H11B 3.5279 no . 4_454
H20B H24B 2.9875 no . 1_565
H21A C19 3.5391 no . 2_646
H21A H19A 3.4614 no . 2_646
H21A H19B 2.7578 no . 2_646
H21B Se1 3.3158 no . 2_656
H21B C4 3.3999 no . 2_646
H21B C19 3.2449 no . 2_646
H21B H4 3.2969 no . 2_646
H21B H19A 2.9102 no . 2_646
H21B H19B 2.6858 no . 2_646
H22A C3 3.5046 no . 2_646
H22A C7 3.4744 no . 2_646
H22A C9 3.3658 no . 2_656
H22A H3 3.4671 no . 2_646
H22A H7A 2.6259 no . 2_646
H22A H8A 3.3654 no . 2_646
H22A H8B 3.4549 no . 2_646
H22A H9A 3.2595 no . 2_656
H22A H9B 2.5872 no . 2_656
H22A H10B 3.3349 no . 4_454
H22A H11A 3.4397 no . 2_656
H22B N2 3.4897 no . 2_646
H22B C1 3.5905 no . 2_646
H22B C3 3.5743 no . 2_646
H22B C7 3.5489 no . 2_646
H22B C8 3.2492 no . 2_646
H22B H7A 3.0341 no . 2_646
H22B H8A 2.5711 no . 2_646
H22B H8B 3.2652 no . 2_646
H22B H19B 2.9646 no . 2_646
H23A C10 3.0100 no . 4_454
H23A H7B 3.5992 no . 4_454
H23A H9B 3.5606 no . 2_656
H23A H10A 2.5280 no . 4_454
H23A H10B 2.6398 no . 4_454
H23A H11B 3.3570 no . 4_454
H23A H13A 3.4879 no . 4_454
H23B C8 3.2706 no . 2_646
H23B H7A 3.4533 no . 2_646
H23B H7B 3.3389 no . 4_454
H23B H8A 3.1297 no . 2_646
H23B H8B 2.5745 no . 2_646
H23B H8B 3.4926 no . 4_454
H23B H10A 3.1727 no . 4_454
H23B H10B 3.1201 no . 4_454
H23B H11A 3.1481 no . 4_444
H23B H11B 3.2575 no . 4_444
H24A H19A 3.0141 no . 1_545
H24B C19 3.3029 no . 1_545
H24B C20 3.3284 no . 1_545
H24B H8A 3.2272 no . 2_646
H24B H8B 3.5014 no . 2_646
H24B H11B 2.8100 no . 4_444
H24B H19A 2.5430 no . 1_545
H24B H20A 3.1811 no . 1_545
H24B H20B 2.9875 no . 1_545
H24B H29A 3.3330 no . 1_545
H25A C11 3.3005 no . 4_444
H25A C12 3.0033 no . 4_444
H25A C13 3.4246 no . 4_444
H25A H7B 3.1057 no . 4_454
H25A H10A 3.5321 no . 4_454
H25A H11A 3.3953 no . 4_444
H25A H11B 2.9044 no . 4_444
H25A H12B 2.2895 no . 4_444
H25A H13B 2.8512 no . 4_444
H25A H16A 3.1350 no . 4_454
H25A H28A 3.5755 no . 2_546
H25B C29 3.3650 no . 1_545
H25B H11B 3.4106 no . 4_444
H25B H12B 3.4223 no . 4_444
H25B H13B 2.8242 no . 4_444
H25B H28A 3.0104 no . 2_546
H25B H29A 2.9999 no . 1_545
H25B H29B 2.8049 no . 1_545
H26A C13 3.3538 no . 4_454
H26A H10A 3.1207 no . 4_454
H26A H13A 2.5162 no . 4_454
H26A H13B 3.3320 no . 4_454
H26A H16A 3.4289 no . 4_454
H26B C13 3.5092 no . 4_454
H26B C16 3.5318 no . 4_454
H26B C28 3.5085 no . 2_546
H26B H13A 2.7293 no . 4_454
H26B H13B 3.5954 no . 4_454
H26B H14B 3.4669 no . 4_454
H26B H16A 2.8830 no . 4_454
H26B H16B 3.2664 no . 4_454
H26B H28A 2.6974 no . 2_546
H26B H28B 3.5341 no . 2_546
H26B H29B 3.5932 no . 2_546
H27A H14B 2.9695 no . 3_657
H27B C13 3.3292 no . 3_657
H27B C14 3.2265 no . 3_657
H27B H13B 2.6769 no . 3_657
H27B H14A 3.3942 no . 3_657
H27B H14B 2.5530 no . 3_657
H27B H28A 2.6409 no . 2_546
H28A C25 3.4850 no . 2_556
H28A C26 3.2763 no . 2_556
H28A C27 3.3856 no . 2_556
H28A H13B 3.2791 no . 3_657
H28A H13B 3.5698 no . 4_454
H28A H25A 3.5755 no . 2_556
H28A H25B 3.0104 no . 2_556
H28A H26B 2.6974 no . 2_556
H28A H27B 2.6409 no . 2_556
H28B C13 3.5897 no . 3_657
H28B C14 3.2176 no . 3_657
H28B H13B 3.0407 no . 3_657
H28B H14A 2.6511 no . 3_657
H28B H14B 3.0694 no . 3_657
H28B H16B 3.1674 no . 3_667
H28B H26B 3.5341 no . 2_556
H29A H11B 3.2997 no . 4_454
H29A H13A 3.3136 no . 4_454
H29A H13B 3.1355 no . 4_454
H29A H24B 3.3330 no . 1_565
H29A H25B 2.9999 no . 1_565
H29B H16B 3.5135 no . 3_667
H29B H25B 2.8049 no . 1_565
H29B H26B 3.5932 no . 2_556

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_chemical_name_systematic        '[Se(IDD)]'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, pentane'
####################################################################### 
# 
# 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_[Se(IMe)]
_database_code_depnum_ccdc_archive 'CCDC 1024810'
_audit_update_record             
;
2014-09-17 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C19 H20 N2 Se'
_chemical_formula_moiety         'C19 H20 N2 Se'
_chemical_formula_weight         355.34
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
_space_group_IT_number           13
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.3318(11)
_cell_length_b                   7.4265(9)
_cell_length_c                   13.6459(19)
_cell_angle_alpha                90.0000
_cell_angle_beta                 98.798(3)
_cell_angle_gamma                90.0000
_cell_volume                     834.42(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2735
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364.00
_exptl_absorpt_coefficient_mu    2.249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_T_max  0.956

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            9772
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_theta_max         25.372
_diffrn_reflns_theta_min         2.694
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1532
_reflns_number_gt                1386
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0736
_refine_ls_wR_factor_gt          0.0718
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1532
_refine_ls_number_parameters     103
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0489P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.25 1.02781(4) 0.25 0.03125(14) Uani 1 2 d . . .
N2 N 0.2281(2) 0.6698(3) 0.32594(12) 0.0268(4) Uani 1 4 d . . .
C1 C 0.25 0.7806(4) 0.25 0.0249(6) Uani 1 2 d . . .
C3 C 0.2361(4) 0.4924(3) 0.29739(19) 0.0388(6) Uani 1 4 d . . .
C4 C 0.1982(3) 0.7248(3) 0.42301(14) 0.0267(5) Uani 1 4 d . . .
C5 C 0.0385(3) 0.7359(3) 0.43984(16) 0.0309(5) Uani 1 4 d . . .
C6 C 0.0129(3) 0.7851(3) 0.53471(17) 0.0375(5) Uani 1 4 d . . .
C7 C 0.1422(3) 0.8174(4) 0.60844(16) 0.0397(6) Uani 1 4 d . . .
C8 C 0.2992(3) 0.8059(4) 0.58973(15) 0.0368(5) Uani 1 4 d . . .
C9 C 0.3317(3) 0.7601(3) 0.49541(15) 0.0295(5) Uani 1 4 d . . .
C10 C -0.1017(3) 0.7012(4) 0.35835(18) 0.0442(6) Uani 1 4 d . . .
C11 C 0.5025(3) 0.7544(4) 0.47224(17) 0.0389(6) Uani 1 4 d . . .
H3 H 0.22417 0.38946 0.33702 0.0466 Uiso 1 4 calc R . .
H6 H -0.09487 0.79653 0.54874 0.0450 Uiso 1 4 calc R . .
H7 H 0.12249 0.84808 0.67313 0.0476 Uiso 1 4 calc R . .
H8 H 0.38668 0.8294 0.64148 0.0441 Uiso 1 4 calc R . .
H10A H -0.10938 0.57186 0.34417 0.0530 Uiso 1 4 calc R . .
H10B H -0.08416 0.76642 0.29846 0.0530 Uiso 1 4 calc R . .
H10C H -0.2027 0.74274 0.37943 0.0530 Uiso 1 4 calc R . .
H11A H 0.52633 0.63304 0.45019 0.0466 Uiso 1 4 calc R . .
H11B H 0.5788 0.78523 0.53185 0.0466 Uiso 1 4 calc R . .
H11C H 0.51349 0.84115 0.41957 0.0466 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Se1 C1 1.836(3) yes . .
N2 C1 1.357(3) yes . .
N2 C3 1.379(3) yes . .
N2 C4 1.444(3) yes . .
C3 C3 1.349(4) yes . 2_555
C4 C5 1.387(3) yes . .
C4 C9 1.395(3) yes . .
C5 C6 1.393(3) yes . .
C5 C10 1.507(3) yes . .
C6 C7 1.378(3) yes . .
C7 C8 1.373(4) yes . .
C8 C9 1.397(3) yes . .
C9 C11 1.504(3) yes . .
C3 H3 0.950 no . .
C6 H6 0.950 no . .
C7 H7 0.950 no . .
C8 H8 0.950 no . .
C10 H10A 0.980 no . .
C10 H10B 0.980 no . .
C10 H10C 0.980 no . .
C11 H11A 0.980 no . .
C11 H11B 0.980 no . .
C11 H11C 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N2 C3 110.23(19) yes . . .
C1 N2 C4 126.22(19) yes . . .
C3 N2 C4 123.54(19) yes . . .
Se1 C1 N2 127.32(13) yes . . .
Se1 C1 N2 127.32(13) yes . . 2_555
N2 C1 N2 105.4(2) yes . . 2_555
N2 C3 C3 107.1(2) yes . . 2_555
N2 C4 C5 118.23(17) yes . . .
N2 C4 C9 118.19(19) yes . . .
C5 C4 C9 123.57(19) yes . . .
C4 C5 C6 117.19(19) yes . . .
C4 C5 C10 121.5(2) yes . . .
C6 C5 C10 121.3(2) yes . . .
C5 C6 C7 120.7(2) yes . . .
C6 C7 C8 120.9(2) yes . . .
C7 C8 C9 120.7(2) yes . . .
C4 C9 C8 116.9(2) yes . . .
C4 C9 C11 121.54(19) yes . . .
C8 C9 C11 121.56(19) yes . . .
N2 C3 H3 126.454 no . . .
C3 C3 H3 126.455 no 2_555 . .
C5 C6 H6 119.659 no . . .
C7 C6 H6 119.663 no . . .
C6 C7 H7 119.530 no . . .
C8 C7 H7 119.529 no . . .
C7 C8 H8 119.636 no . . .
C9 C8 H8 119.645 no . . .
C5 C10 H10A 109.474 no . . .
C5 C10 H10B 109.469 no . . .
C5 C10 H10C 109.468 no . . .
H10A C10 H10B 109.475 no . . .
H10A C10 H10C 109.468 no . . .
H10B C10 H10C 109.474 no . . .
C9 C11 H11A 109.473 no . . .
C9 C11 H11B 109.479 no . . .
C9 C11 H11C 109.471 no . . .
H11A C11 H11B 109.469 no . . .
H11A C11 H11C 109.464 no . . .
H11B C11 H11C 109.471 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N2 C3 C3 0.2(2) no . . . 2_555
C3 N2 C1 Se1 179.91(14) no . . . .
C3 N2 C1 N2 -0.09(18) no . . . 2_555
C1 N2 C4 C5 94.5(2) no . . . .
C1 N2 C4 C9 -86.9(2) no . . . .
C4 N2 C1 Se1 0.7(2) no . . . .
C4 N2 C1 N2 -179.30(15) no . . . 2_555
C3 N2 C4 C5 -84.6(3) no . . . .
C3 N2 C4 C9 94.0(2) no . . . .
C4 N2 C3 C3 179.47(17) no . . . 2_555
N2 C3 C3 N2 -0.3(3) no . . 2_555 2_555
N2 C4 C5 C6 178.49(16) no . . . .
N2 C4 C5 C10 -3.1(3) no . . . .
N2 C4 C9 C8 -177.44(16) no . . . .
N2 C4 C9 C11 4.3(3) no . . . .
C5 C4 C9 C8 1.1(3) no . . . .
C5 C4 C9 C11 -177.20(18) no . . . .
C9 C4 C5 C6 -0.0(3) no . . . .
C9 C4 C5 C10 178.36(18) no . . . .
C4 C5 C6 C7 -1.3(3) no . . . .
C10 C5 C6 C7 -179.7(2) no . . . .
C5 C6 C7 C8 1.5(4) no . . . .
C6 C7 C8 C9 -0.4(4) no . . . .
C7 C8 C9 C4 -0.9(3) no . . . .
C7 C8 C9 C11 177.4(2) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Se1 C4 3.337(2) no . .
Se1 C4 3.337(2) no . 2_555
N2 C4 3.567(3) no . 2_555
N2 C10 2.858(3) no . .
N2 C11 2.865(3) no . .
C1 C3 2.244(4) no . 2_555
C1 C4 2.499(2) no . 2_555
C1 C5 3.365(2) no . .
C1 C5 3.365(2) no . 2_555
C1 C9 3.317(2) no . .
C1 C9 3.317(2) no . 2_555
C1 C10 3.528(3) no . .
C1 C10 3.528(3) no . 2_555
C1 C11 3.422(2) no . .
C1 C11 3.422(2) no . 2_555
C3 C4 3.582(3) no . 2_555
C3 C5 3.277(4) no . .
C3 C9 3.352(3) no . .
C3 C10 3.425(4) no . .
C3 C11 3.576(3) no . .
C4 C7 2.730(3) no . .
C5 C8 2.795(3) no . .
C6 C9 2.796(3) no . .
Se1 C3 3.515(2) no . 1_565
Se1 C3 3.515(2) no . 2_565
C3 Se1 3.515(2) no . 1_545
C6 C6 3.327(3) no . 3_576
C10 C10 3.552(3) no . 2_455
Se1 H10B 3.5384 no . .
Se1 H10B 3.5384 no . 2_555
Se1 H11C 3.2468 no . .
Se1 H11C 3.2468 no . 2_555
N2 H3 3.1158 no . 2_555
N2 H10A 2.9512 no . .
N2 H10B 2.6692 no . .
N2 H11A 2.7992 no . .
N2 H11C 2.8245 no . .
C1 H3 3.1579 no . .
C1 H3 3.1579 no . 2_555
C1 H10B 2.9603 no . .
C1 H10B 2.9603 no . 2_555
C1 H11A 3.4699 no . .
C1 H11A 3.4699 no . 2_555
C1 H11C 2.9702 no . .
C1 H11C 2.9702 no . 2_555
C3 H10A 3.0987 no . .
C3 H10B 3.3576 no . .
C3 H11A 3.1218 no . .
C4 H3 2.7758 no . .
C4 H6 3.2361 no . .
C4 H8 3.2441 no . .
C4 H10A 2.8589 no . .
C4 H10B 2.7012 no . .
C4 H10C 3.3049 no . .
C4 H11A 2.7866 no . .
C4 H11B 3.3197 no . .
C4 H11C 2.7723 no . .
C5 H3 3.4124 no . .
C5 H7 3.2613 no . .
C6 H8 3.2468 no . .
C6 H10A 3.0816 no . .
C6 H10B 3.2045 no . .
C6 H10C 2.5790 no . .
C8 H6 3.2462 no . .
C8 H11A 3.1555 no . .
C8 H11B 2.5760 no . .
C8 H11C 3.1488 no . .
C9 H3 3.5298 no . .
C9 H7 3.2621 no . .
C10 H6 2.6850 no . .
C11 H8 2.6937 no . .
H3 H3 2.4776 no . 2_555
H3 H10A 3.1065 no . .
H3 H11A 3.2872 no . .
H6 H7 2.3167 no . .
H6 H10A 3.2385 no . .
H6 H10B 3.4374 no . .
H6 H10C 2.3811 no . .
H7 H8 2.3112 no . .
H8 H11A 3.3501 no . .
H8 H11B 2.3750 no . .
H8 H11C 3.3574 no . .
H10B H11C 3.1690 no . 2_555
Se1 H3 2.9577 no . 1_565
Se1 H3 2.9577 no . 2_565
Se1 H6 3.4642 no . 3_576
Se1 H6 3.4642 no . 4_574
Se1 H7 3.5465 no . 3_576
Se1 H7 3.5465 no . 4_574
Se1 H8 3.3331 no . 3_676
Se1 H8 3.3331 no . 4_474
Se1 H11B 3.3949 no . 3_676
Se1 H11B 3.3949 no . 4_474
C3 H6 3.3393 no . 3_566
C3 H11B 3.3105 no . 3_666
C5 H6 3.5041 no . 3_576
C6 H3 3.1150 no . 3_566
C6 H6 3.4138 no . 3_576
C6 H10A 3.1623 no . 3_566
C7 H3 3.5957 no . 3_566
C7 H6 3.5660 no . 3_576
C7 H7 3.3154 no . 2_556
C7 H8 3.4588 no . 2_556
C7 H10A 2.9842 no . 3_566
C7 H10B 3.4040 no . 3_576
C7 H10C 3.3053 no . 3_576
C8 H7 3.2170 no . 2_556
C8 H10A 3.4094 no . 3_566
C8 H10C 3.4873 no . 3_576
C8 H11C 3.0628 no . 3_676
C9 H11A 3.1947 no . 3_666
C9 H11B 3.4899 no . 3_676
C9 H11C 3.3645 no . 3_676
C10 H7 3.3758 no . 3_576
C10 H10A 3.5100 no . 2_455
C10 H10B 3.1546 no . 2_455
C10 H10C 3.4150 no . 2_455
C10 H11A 3.5526 no . 1_455
C10 H11C 3.5886 no . 1_455
C11 H3 3.3601 no . 3_666
C11 H6 3.3723 no . 1_655
C11 H10C 2.9322 no . 1_655
C11 H11A 3.0878 no . 3_666
C11 H11B 3.4842 no . 3_676
C11 H11C 3.3585 no . 3_676
H3 Se1 2.9577 no . 1_545
H3 C6 3.1150 no . 3_566
H3 C7 3.5957 no . 3_566
H3 C11 3.3601 no . 3_666
H3 H6 2.4520 no . 3_566
H3 H7 3.3691 no . 3_566
H3 H8 3.5985 no . 3_666
H3 H11A 3.3067 no . 3_666
H3 H11B 2.5848 no . 3_666
H6 Se1 3.4642 no . 3_576
H6 C3 3.3393 no . 3_566
H6 C5 3.5041 no . 3_576
H6 C6 3.4138 no . 3_576
H6 C7 3.5660 no . 3_576
H6 C11 3.3723 no . 1_455
H6 H3 2.4520 no . 3_566
H6 H10A 3.4287 no . 3_566
H6 H11A 3.4562 no . 1_455
H6 H11B 2.6946 no . 1_455
H6 H11C 3.4792 no . 1_455
H7 Se1 3.5465 no . 3_576
H7 C7 3.3154 no . 2_556
H7 C8 3.2170 no . 2_556
H7 C10 3.3758 no . 3_576
H7 H3 3.3691 no . 3_566
H7 H7 2.7481 no . 2_556
H7 H8 2.5464 no . 2_556
H7 H10A 3.1283 no . 3_566
H7 H10B 2.9132 no . 3_576
H7 H10C 3.2159 no . 3_576
H8 Se1 3.3331 no . 3_676
H8 C7 3.4588 no . 2_556
H8 H3 3.5985 no . 3_666
H8 H7 2.5464 no . 2_556
H8 H10C 3.5205 no . 3_576
H8 H11C 2.7539 no . 3_676
H10A C6 3.1623 no . 3_566
H10A C7 2.9842 no . 3_566
H10A C8 3.4094 no . 3_566
H10A C10 3.5100 no . 2_455
H10A H6 3.4287 no . 3_566
H10A H7 3.1283 no . 3_566
H10A H10A 3.2021 no . 2_455
H10A H10B 3.2978 no . 2_455
H10A H10C 3.4512 no . 2_455
H10A H11A 3.5854 no . 1_455
H10B C7 3.4040 no . 3_576
H10B C10 3.1546 no . 2_455
H10B H7 2.9132 no . 3_576
H10B H10A 3.2978 no . 2_455
H10B H10B 2.8754 no . 2_455
H10B H10C 2.7854 no . 2_455
H10C C7 3.3053 no . 3_576
H10C C8 3.4873 no . 3_576
H10C C10 3.4150 no . 2_455
H10C C11 2.9322 no . 1_455
H10C H7 3.2159 no . 3_576
H10C H8 3.5205 no . 3_576
H10C H10A 3.4512 no . 2_455
H10C H10B 2.7854 no . 2_455
H10C H10C 3.4996 no . 2_455
H10C H11A 2.7129 no . 1_455
H10C H11B 2.9830 no . 1_455
H10C H11C 2.6119 no . 1_455
H11A C9 3.1947 no . 3_666
H11A C10 3.5526 no . 1_655
H11A C11 3.0878 no . 3_666
H11A H3 3.3067 no . 3_666
H11A H6 3.4562 no . 1_655
H11A H10A 3.5854 no . 1_655
H11A H10C 2.7129 no . 1_655
H11A H11A 2.4754 no . 3_666
H11A H11B 3.2468 no . 3_666
H11B Se1 3.3949 no . 3_676
H11B C3 3.3105 no . 3_666
H11B C9 3.4899 no . 3_676
H11B C11 3.4842 no . 3_676
H11B H3 2.5848 no . 3_666
H11B H6 2.6946 no . 1_655
H11B H10C 2.9830 no . 1_655
H11B H11A 3.2468 no . 3_666
H11B H11B 3.5081 no . 3_676
H11B H11C 2.9809 no . 3_676
H11C C8 3.0628 no . 3_676
H11C C9 3.3645 no . 3_676
H11C C10 3.5886 no . 1_655
H11C C11 3.3585 no . 3_676
H11C H6 3.4792 no . 1_655
H11C H8 2.7539 no . 3_676
H11C H10C 2.6119 no . 1_655
H11C H11B 2.9809 no . 3_676
H11C H11C 3.2537 no . 3_676

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_chemical_name_systematic        '[Se(IMe)]'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone, pentane'
####################################################################### 
# 
# 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_[Se(IMes)]
_database_code_depnum_ccdc_archive 'CCDC 1024811'
_audit_update_record             
;
2014-09-17 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21 H24 N2 Se'
_chemical_formula_moiety         'C21 H24 N2 Se'
_chemical_formula_weight         383.39
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
_space_group_IT_number           60
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,-Y,1/2+Z
4 1/2-X,1/2-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,-Z
7 -X,+Y,1/2-Z
8 1/2+X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   16.043(2)
_cell_length_b                   7.3937(9)
_cell_length_c                   16.055(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1904.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4164
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792.00
_exptl_absorpt_coefficient_mu    1.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_T_max  0.888

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            21284
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_theta_max         25.383
_diffrn_reflns_theta_min         2.537
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1745
_reflns_number_gt                1402
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.1917
_refine_ls_wR_factor_gt          0.1823
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1745
_refine_ls_number_parameters     113
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1188P)²+2.6816P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         2.44
_refine_diff_density_min         -0.94
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.0 0.02035(9) 0.75 0.0442(3) Uani 1 4 d . . .
N2 N 0.0318(2) 0.3801(5) 0.6907(2) 0.0328(8) Uani 1 8 d . . .
C1 C 0.0 0.2686(9) 0.75 0.0328(13) Uani 1 4 d . . .
C3 C 0.0203(3) 0.5586(7) 0.7138(3) 0.0430(11) Uani 1 8 d . . .
C4 C 0.0737(3) 0.3210(6) 0.6159(2) 0.0316(9) Uani 1 8 d . . .
C5 C 0.0265(3) 0.2678(6) 0.5477(2) 0.0304(9) Uani 1 8 d . . .
C6 C 0.0694(3) 0.2126(6) 0.4773(3) 0.0327(9) Uani 1 8 d . . .
C7 C 0.1556(3) 0.2138(6) 0.4727(3) 0.0350(10) Uani 1 8 d . . .
C8 C 0.1999(3) 0.2716(7) 0.5424(3) 0.0434(11) Uani 1 8 d . . .
C9 C 0.1600(3) 0.3238(6) 0.6153(2) 0.0386(10) Uani 1 8 d . . .
C10 C -0.0671(3) 0.2711(6) 0.5490(3) 0.0392(10) Uani 1 8 d . . .
C11 C 0.1996(3) 0.1568(8) 0.3941(3) 0.0515(13) Uani 1 8 d . . .
C12 C 0.2088(3) 0.3798(9) 0.6914(3) 0.0591(15) Uani 1 8 d . . .
H3 H 0.03815 0.66219 0.68367 0.0516 Uiso 1 8 calc R . .
H6 H 0.03852 0.17237 0.43034 0.0392 Uiso 1 8 calc R . .
H8 H 0.25908 0.27535 0.54002 0.0520 Uiso 1 8 calc R . .
H10A H -0.08853 0.2152 0.49793 0.0470 Uiso 1 8 calc R . .
H10B H -0.08645 0.39655 0.55231 0.0470 Uiso 1 8 calc R . .
H10C H -0.08726 0.20359 0.59746 0.0470 Uiso 1 8 calc R . .
H11A H 0.20999 0.26316 0.35922 0.0618 Uiso 1 8 calc R . .
H11B H 0.16475 0.07048 0.36359 0.0618 Uiso 1 8 calc R . .
H11C H 0.25283 0.09949 0.40844 0.0618 Uiso 1 8 calc R . .
H12A H 0.19647 0.50633 0.70465 0.0709 Uiso 1 8 calc R . .
H12B H 0.26856 0.36638 0.68029 0.0709 Uiso 1 8 calc R . .
H12C H 0.19309 0.30291 0.73854 0.0709 Uiso 1 8 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Se1 C1 1.835(7) yes . .
N2 C1 1.359(5) yes . .
N2 C3 1.384(6) yes . .
N2 C4 1.444(5) yes . .
C3 C3 1.332(7) yes . 7_556
C4 C5 1.387(5) yes . .
C4 C9 1.385(6) yes . .
C5 C6 1.385(6) yes . .
C5 C10 1.502(6) yes . .
C6 C7 1.384(6) yes . .
C7 C8 1.394(6) yes . .
C7 C11 1.506(6) yes . .
C8 C9 1.389(6) yes . .
C9 C12 1.508(6) yes . .
C3 H3 0.950 no . .
C6 H6 0.950 no . .
C8 H8 0.950 no . .
C10 H10A 0.980 no . .
C10 H10B 0.980 no . .
C10 H10C 0.980 no . .
C11 H11A 0.980 no . .
C11 H11B 0.980 no . .
C11 H11C 0.980 no . .
C12 H12A 0.980 no . .
C12 H12B 0.980 no . .
C12 H12C 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N2 C3 109.9(4) yes . . .
C1 N2 C4 125.1(4) yes . . .
C3 N2 C4 125.0(4) yes . . .
Se1 C1 N2 127.3(3) yes . . .
Se1 C1 N2 127.3(3) yes . . 7_556
N2 C1 N2 105.3(5) yes . . 7_556
N2 C3 C3 107.4(5) yes . . 7_556
N2 C4 C5 119.2(4) yes . . .
N2 C4 C9 117.8(3) yes . . .
C5 C4 C9 123.0(4) yes . . .
C4 C5 C6 117.2(4) yes . . .
C4 C5 C10 122.0(4) yes . . .
C6 C5 C10 120.8(4) yes . . .
C5 C6 C7 122.6(4) yes . . .
C6 C7 C8 117.9(4) yes . . .
C6 C7 C11 120.8(4) yes . . .
C8 C7 C11 121.3(4) yes . . .
C7 C8 C9 121.8(4) yes . . .
C4 C9 C8 117.5(4) yes . . .
C4 C9 C12 121.2(4) yes . . .
C8 C9 C12 121.3(4) yes . . .
N2 C3 H3 126.290 no . . .
C3 C3 H3 126.293 no 7_556 . .
C5 C6 H6 118.719 no . . .
C7 C6 H6 118.723 no . . .
C7 C8 H8 119.112 no . . .
C9 C8 H8 119.104 no . . .
C5 C10 H10A 109.470 no . . .
C5 C10 H10B 109.467 no . . .
C5 C10 H10C 109.464 no . . .
H10A C10 H10B 109.486 no . . .
H10A C10 H10C 109.472 no . . .
H10B C10 H10C 109.469 no . . .
C7 C11 H11A 109.476 no . . .
C7 C11 H11B 109.473 no . . .
C7 C11 H11C 109.465 no . . .
H11A C11 H11B 109.477 no . . .
H11A C11 H11C 109.466 no . . .
H11B C11 H11C 109.471 no . . .
C9 C12 H12A 109.471 no . . .
C9 C12 H12B 109.476 no . . .
C9 C12 H12C 109.468 no . . .
H12A C12 H12B 109.480 no . . .
H12A C12 H12C 109.463 no . . .
H12B C12 H12C 109.468 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N2 C3 C3 -1.6(5) no . . . 7_556
C3 N2 C1 Se1 -179.4(3) no . . . .
C3 N2 C1 N2 0.6(3) no . . . 7_556
C1 N2 C4 C5 81.7(4) no . . . .
C1 N2 C4 C9 -99.6(4) no . . . .
C4 N2 C1 Se1 -1.3(4) no . . . .
C4 N2 C1 N2 178.7(3) no . . . 7_556
C3 N2 C4 C5 -100.4(5) no . . . .
C3 N2 C4 C9 78.3(5) no . . . .
C4 N2 C3 C3 -179.7(3) no . . . 7_556
N2 C3 C3 N2 1.9(5) no . . 7_556 7_556
N2 C4 C5 C6 179.9(3) no . . . .
N2 C4 C5 C10 0.5(6) no . . . .
N2 C4 C9 C8 -178.3(3) no . . . .
N2 C4 C9 C12 2.3(6) no . . . .
C5 C4 C9 C8 0.4(6) no . . . .
C5 C4 C9 C12 -179.0(4) no . . . .
C9 C4 C5 C6 1.2(6) no . . . .
C9 C4 C5 C10 -178.2(4) no . . . .
C4 C5 C6 C7 -1.7(6) no . . . .
C10 C5 C6 C7 177.7(3) no . . . .
C5 C6 C7 C8 0.6(6) no . . . .
C5 C6 C7 C11 -178.5(4) no . . . .
C6 C7 C8 C9 1.1(7) no . . . .
C11 C7 C8 C9 -179.7(4) no . . . .
C7 C8 C9 C4 -1.6(7) no . . . .
C7 C8 C9 C12 177.8(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Se1 C4 3.313(4) no . .
Se1 C4 3.313(4) no . 7_556
N2 C4 3.564(5) no . 7_556
N2 C10 2.888(6) no . .
N2 C12 2.840(6) no . .
C1 C3 2.245(8) no . 7_556
C1 C4 2.487(4) no . 7_556
C1 C5 3.276(4) no . .
C1 C5 3.276(4) no . 7_556
C1 C9 3.381(4) no . .
C1 C9 3.381(4) no . 7_556
C1 C10 3.402(4) no . .
C1 C10 3.402(4) no . 7_556
C1 C12 3.575(5) no . .
C1 C12 3.575(5) no . 7_556
C3 C4 3.583(6) no . 7_556
C3 C5 3.428(7) no . .
C3 C9 3.246(7) no . .
C3 C12 3.320(8) no . .
C4 C7 2.764(6) no . .
C5 C8 2.783(6) no . .
C6 C9 2.774(6) no . .
Se1 C3 3.478(6) no . 1_545
Se1 C3 3.478(6) no . 7_546
C3 Se1 3.478(6) no . 1_565
C11 C12 3.582(7) no . 4_554
C12 C11 3.582(7) no . 4_555
Se1 H10C 3.1293 no . .
Se1 H10C 3.1293 no . 7_556
N2 H3 3.1113 no . 7_556
N2 H10B 2.9235 no . .
N2 H10C 2.7547 no . .
N2 H12A 2.8112 no . .
N2 H12C 2.7591 no . .
C1 H3 3.1587 no . .
C1 H3 3.1587 no . 7_556
C1 H10B 3.5905 no . .
C1 H10B 3.5905 no . 7_556
C1 H10C 2.8615 no . .
C1 H10C 2.8615 no . 7_556
C1 H12C 3.1135 no . .
C1 H12C 3.1135 no . 7_556
C3 H10B 3.3308 no . .
C3 H12A 2.8562 no . .
C3 H12C 3.3787 no . .
C4 H3 2.8060 no . .
C4 H6 3.2246 no . .
C4 H8 3.2318 no . .
C4 H10A 3.3118 no . .
C4 H10B 2.8199 no . .
C4 H10C 2.7398 no . .
C4 H12A 2.7911 no . .
C4 H12B 3.3102 no . .
C4 H12C 2.7508 no . .
C6 H8 3.2382 no . .
C6 H10A 2.5557 no . .
C6 H10B 3.0909 no . .
C6 H10C 3.1694 no . .
C6 H11A 2.9694 no . .
C6 H11B 2.6029 no . .
C6 H11C 3.2524 no . .
C8 H6 3.2374 no . .
C8 H11A 2.9460 no . .
C8 H11B 3.2819 no . .
C8 H11C 2.6391 no . .
C8 H12A 3.1306 no . .
C8 H12B 2.5698 no . .
C8 H12C 3.1594 no . .
C9 H3 3.3594 no . .
C10 H6 2.6510 no . .
C11 H6 2.6517 no . .
C11 H8 2.6768 no . .
C12 H3 3.4455 no . .
C12 H8 2.6738 no . .
H3 H3 2.4565 no . 7_556
H3 H10B 3.5073 no . .
H3 H12A 2.8093 no . .
H6 H10A 2.3307 no . .
H6 H10B 3.2560 no . .
H6 H10C 3.3651 no . .
H6 H11A 3.0531 no . .
H6 H11B 2.4118 no . .
H6 H11C 3.4978 no . .
H8 H11A 3.0090 no . .
H8 H11B 3.5507 no . .
H8 H11C 2.4826 no . .
H8 H12A 3.3032 no . .
H8 H12B 2.3553 no . .
H8 H12C 3.3646 no . .
H10C H12C 3.2178 no . 7_556
Se1 H3 2.9191 no . 1_545
Se1 H3 2.9191 no . 7_546
Se1 H6 3.2856 no . 3_555
Se1 H6 3.2856 no . 5_556
Se1 H11B 3.2806 no . 3_555
Se1 H11B 3.2806 no . 5_556
C3 H6 3.1943 no . 5_566
C4 H10B 3.4196 no . 5_566
C5 H6 3.4361 no . 5_556
C5 H10B 3.1078 no . 5_566
C6 H3 3.2424 no . 5_566
C6 H10A 3.2029 no . 5_556
C6 H10B 2.9411 no . 5_566
C6 H10C 3.3155 no . 5_556
C7 H10A 3.3827 no . 5_556
C7 H10B 3.1128 no . 5_566
C7 H10C 3.4632 no . 5_556
C7 H11C 3.3693 no . 2_555
C8 H10A 3.4561 no . 6_556
C8 H10B 3.4128 no . 5_566
C8 H11C 3.3282 no . 2_555
C9 H10B 3.5928 no . 5_566
C9 H12A 3.5874 no . 2_545
C10 H6 3.3272 no . 5_556
C10 H8 3.1524 no . 6_456
C10 H11B 3.2871 no . 5_556
C10 H11C 3.1197 no . 6_456
C11 H10B 3.5598 no . 6_556
C11 H10C 3.2197 no . 5_556
C11 H10C 3.5739 no . 6_556
C11 H11A 3.2993 no . 2_545
C11 H11C 3.3689 no . 2_555
C11 H12B 3.4749 no . 4_554
C11 H12C 3.0479 no . 4_554
C12 H11A 3.1744 no . 4_555
C12 H11B 3.4491 no . 4_555
C12 H11C 3.5426 no . 4_555
C12 H12A 3.1588 no . 2_545
C12 H12C 3.5832 no . 2_555
H3 Se1 2.9191 no . 1_565
H3 C6 3.2424 no . 5_566
H3 H6 2.5218 no . 5_566
H3 H10A 3.1584 no . 5_566
H3 H12B 3.4493 no . 2_555
H6 Se1 3.2856 no . 3_554
H6 C3 3.1943 no . 5_566
H6 C5 3.4361 no . 5_556
H6 C10 3.3272 no . 5_556
H6 H3 2.5218 no . 5_566
H6 H10A 3.1908 no . 5_556
H6 H10B 3.2905 no . 5_566
H6 H10C 2.9219 no . 5_556
H8 C10 3.1524 no . 6_556
H8 H10A 2.5205 no . 6_556
H8 H10B 3.1549 no . 6_556
H8 H10C 3.3125 no . 6_556
H8 H11C 3.2004 no . 2_555
H8 H12A 3.3839 no . 2_545
H10A C6 3.2029 no . 5_556
H10A C7 3.3827 no . 5_556
H10A C8 3.4561 no . 6_456
H10A H3 3.1584 no . 5_566
H10A H6 3.1908 no . 5_556
H10A H8 2.5205 no . 6_456
H10A H11B 3.3014 no . 5_556
H10A H11C 3.2579 no . 6_456
H10B C4 3.4196 no . 5_566
H10B C5 3.1078 no . 5_566
H10B C6 2.9411 no . 5_566
H10B C7 3.1128 no . 5_566
H10B C8 3.4128 no . 5_566
H10B C9 3.5928 no . 5_566
H10B C11 3.5598 no . 6_456
H10B H6 3.2905 no . 5_566
H10B H8 3.1549 no . 6_456
H10B H10B 3.5854 no . 5_566
H10B H11A 3.5037 no . 5_566
H10B H11C 2.6544 no . 6_456
H10C C6 3.3155 no . 5_556
H10C C7 3.4632 no . 5_556
H10C C11 3.2197 no . 5_556
H10C C11 3.5739 no . 6_456
H10C H6 2.9219 no . 5_556
H10C H8 3.3125 no . 6_456
H10C H11A 3.3352 no . 6_456
H10C H11B 2.4582 no . 5_556
H10C H11C 3.4765 no . 5_556
H10C H11C 2.9513 no . 6_456
H11A C11 3.2993 no . 2_555
H11A C12 3.1744 no . 4_554
H11A H10B 3.5037 no . 5_566
H11A H10C 3.3352 no . 6_556
H11A H11B 3.0341 no . 2_555
H11A H11C 2.6766 no . 2_555
H11A H12A 3.0183 no . 3_564
H11A H12A 3.5186 no . 4_554
H11A H12B 3.0476 no . 4_554
H11A H12C 2.5318 no . 4_554
H11B Se1 3.2806 no . 3_554
H11B C10 3.2871 no . 5_556
H11B C12 3.4491 no . 4_554
H11B H10A 3.3014 no . 5_556
H11B H10C 2.4582 no . 5_556
H11B H11A 3.0341 no . 2_545
H11B H12A 3.4338 no . 4_554
H11B H12B 3.1659 no . 4_554
H11B H12C 3.4437 no . 3_554
H11B H12C 3.1793 no . 4_554
H11C C7 3.3693 no . 2_545
H11C C8 3.3282 no . 2_545
H11C C10 3.1197 no . 6_556
H11C C11 3.3689 no . 2_545
H11C C12 3.5426 no . 4_554
H11C H8 3.2004 no . 2_545
H11C H10A 3.2579 no . 6_556
H11C H10B 2.6544 no . 6_556
H11C H10C 3.4765 no . 5_556
H11C H10C 2.9513 no . 6_556
H11C H11A 2.6766 no . 2_545
H11C H12A 3.4610 no . 4_554
H11C H12C 2.9519 no . 4_554
H12A C9 3.5874 no . 2_555
H12A C12 3.1588 no . 2_555
H12A H8 3.3839 no . 2_555
H12A H11A 3.0183 no . 3_565
H12A H11A 3.5186 no . 4_555
H12A H11B 3.4338 no . 4_555
H12A H11C 3.4610 no . 4_555
H12A H12B 2.7485 no . 2_555
H12A H12C 2.8712 no . 2_555
H12B C11 3.4749 no . 4_555
H12B H3 3.4493 no . 2_545
H12B H11A 3.0476 no . 4_555
H12B H11B 3.1659 no . 4_555
H12B H12A 2.7485 no . 2_545
H12B H12C 3.4162 no . 2_555
H12C C11 3.0479 no . 4_555
H12C C12 3.5832 no . 2_545
H12C H11A 2.5318 no . 4_555
H12C H11B 3.4437 no . 3_555
H12C H11B 3.1793 no . 4_555
H12C H11C 2.9519 no . 4_555
H12C H12A 2.8712 no . 2_545
H12C H12B 3.4162 no . 2_545

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_chemical_name_systematic        '[Se(IMes)]'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform, pentane'
####################################################################### 
# 
# 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_[Se(IPent)]
_database_code_depnum_ccdc_archive 'CCDC 1024812'
_audit_update_record             
;
2014-09-17 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C35 H52 N2 Se'
_chemical_formula_moiety         'C35 H52 N2 Se'
_chemical_formula_weight         579.77
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   20.433(2)
_cell_length_b                   7.6327(6)
_cell_length_c                   21.563(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.660(3)
_cell_angle_gamma                90.0000
_cell_volume                     3221.7(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7799
_cell_measurement_theta_min      1.95
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240.00
_exptl_absorpt_coefficient_mu    1.190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_T_max  0.976

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            37896
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_theta_max         25.391
_diffrn_reflns_theta_min         1.948
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             5921
_reflns_number_gt                4779
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1060
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5921
_refine_ls_number_parameters     351
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0500P)²+3.3801P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.63
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.22267(2) 1.16079(4) 0.28112(2) 0.03934(12) Uani 1 4 d . . .
N2 N 0.19583(11) 0.7960(3) 0.25089(10) 0.0265(5) Uani 1 4 d . . .
N5 N 0.30099(11) 0.8651(3) 0.26105(11) 0.0322(5) Uani 1 4 d . . .
C1 C 0.24021(13) 0.9341(3) 0.26342(12) 0.0282(6) Uani 1 4 d . . .
C3 C 0.22904(14) 0.6447(4) 0.24105(13) 0.0329(6) Uani 1 4 d . . .
C4 C 0.29374(14) 0.6872(4) 0.24761(15) 0.0369(7) Uani 1 4 d . . .
C6 C 0.12464(13) 0.8021(3) 0.24918(13) 0.0269(6) Uani 1 4 d . . .
C7 C 0.07573(13) 0.8196(3) 0.18904(13) 0.0290(6) Uani 1 4 d . . .
C8 C 0.00739(14) 0.8193(4) 0.18881(14) 0.0343(6) Uani 1 4 d . . .
C9 C -0.01095(14) 0.7964(4) 0.24500(15) 0.0371(7) Uani 1 4 d . . .
C10 C 0.03893(15) 0.7772(4) 0.30342(14) 0.0358(6) Uani 1 4 d . . .
C11 C 0.10791(14) 0.7799(3) 0.30707(13) 0.0295(6) Uani 1 4 d . . .
C12 C 0.09412(14) 0.8371(3) 0.12589(13) 0.0311(6) Uani 1 4 d . . .
C13 C 0.05520(16) 0.7043(4) 0.07554(14) 0.0379(7) Uani 1 4 d . . .
C14 C 0.06619(18) 0.5144(4) 0.09743(17) 0.0484(8) Uani 1 4 d . . .
C15 C 0.08375(15) 1.0265(4) 0.10078(14) 0.0371(7) Uani 1 4 d . . .
C16 C 0.10868(18) 1.0581(4) 0.04202(15) 0.0469(8) Uani 1 4 d . . .
C17 C 0.16278(15) 0.7469(4) 0.37059(13) 0.0333(6) Uani 1 4 d . . .
C18 C 0.17469(16) 0.5476(4) 0.38051(14) 0.0407(7) Uani 1 4 d . . .
C19 C 0.23924(18) 0.4997(5) 0.43242(17) 0.0552(9) Uani 1 4 d . . .
C20 C 0.14701(17) 0.8326(4) 0.42941(14) 0.0445(7) Uani 1 4 d . . .
C21 C 0.1395(2) 1.0290(5) 0.42435(17) 0.0566(9) Uani 1 4 d . . .
C22 C 0.36604(14) 0.9551(4) 0.27655(15) 0.0383(7) Uani 1 4 d . . .
C23 C 0.38007(15) 1.0645(4) 0.23062(16) 0.0445(8) Uani 1 4 d . . .
C24 C 0.44516(18) 1.1413(5) 0.2466(2) 0.0616(10) Uani 1 4 d . . .
C25 C 0.49192(18) 1.1093(6) 0.3054(2) 0.0693(11) Uani 1 4 d . . .
C26 C 0.47667(17) 0.9999(6) 0.34974(18) 0.0608(10) Uani 1 4 d . . .
C27 C 0.41324(15) 0.9200(5) 0.33684(16) 0.0471(8) Uani 1 4 d . . .
C28 C 0.32944(17) 1.1058(4) 0.16536(16) 0.0467(8) Uani 1 4 d . . .
C29 C 0.3505(2) 1.0123(6) 0.1095(2) 0.0776(13) Uani 1 4 d . . .
C30 C 0.3342(3) 0.8229(6) 0.1035(2) 0.0820(14) Uani 1 4 d . . .
C31 C 0.3227(2) 1.3029(5) 0.1541(2) 0.0640(10) Uani 1 4 d . . .
C32 C 0.2608(2) 1.3571(5) 0.1009(2) 0.0786(13) Uani 1 4 d . . .
C33 C 0.39964(19) 0.7927(6) 0.38605(18) 0.0619(10) Uani 1 4 d . . .
C34 C 0.4448(2) 0.6188(7) 0.3876(3) 0.0891(15) Uani 1 4 d . . .
C35 C 0.4247(4) 0.4658(9) 0.4147(4) 0.139(3) Uani 1 4 d . . .
C36 C 0.4104(2) 0.8686(7) 0.4521(2) 0.0824(14) Uani 1 4 d . . .
C37 C 0.3614(3) 1.0138(7) 0.4546(3) 0.0944(16) Uani 1 4 d . . .
H3 H 0.20925 0.53169 0.23141 0.0395 Uiso 1 4 calc R . .
H4 H 0.32876 0.60973 0.24378 0.0443 Uiso 1 4 calc R . .
H8 H -0.02726 0.8352 0.14906 0.0412 Uiso 1 4 calc R . .
H9 H -0.05783 0.79377 0.24359 0.0446 Uiso 1 4 calc R . .
H10 H 0.02575 0.76189 0.34189 0.0429 Uiso 1 4 calc R . .
H12 H 0.14388 0.80973 0.13534 0.0373 Uiso 1 4 calc R . .
H13A H 0.00578 0.731 0.06452 0.0455 Uiso 1 4 calc R . .
H13B H 0.06946 0.71858 0.03566 0.0455 Uiso 1 4 calc R . .
H14A H 0.05233 0.49864 0.13698 0.0580 Uiso 1 4 calc R . .
H14B H 0.1146 0.48436 0.10608 0.0580 Uiso 1 4 calc R . .
H14C H 0.0387 0.43788 0.06333 0.0580 Uiso 1 4 calc R . .
H15A H 0.03451 1.05547 0.08962 0.0446 Uiso 1 4 calc R . .
H15B H 0.10827 1.10664 0.13587 0.0446 Uiso 1 4 calc R . .
H16A H 0.07996 0.99285 0.00503 0.0562 Uiso 1 4 calc R . .
H16B H 0.15612 1.01846 0.05114 0.0562 Uiso 1 4 calc R . .
H16C H 0.1061 1.18354 0.03185 0.0562 Uiso 1 4 calc R . .
H17 H 0.20621 0.79963 0.36664 0.0400 Uiso 1 4 calc R . .
H18A H 0.13522 0.49568 0.39183 0.0488 Uiso 1 4 calc R . .
H18B H 0.17644 0.49479 0.33907 0.0488 Uiso 1 4 calc R . .
H19A H 0.23618 0.54146 0.47447 0.0662 Uiso 1 4 calc R . .
H19B H 0.27855 0.55441 0.42267 0.0662 Uiso 1 4 calc R . .
H19C H 0.24489 0.37211 0.4338 0.0662 Uiso 1 4 calc R . .
H20A H 0.10421 0.78176 0.43437 0.0534 Uiso 1 4 calc R . .
H20B H 0.1842 0.80351 0.46888 0.0534 Uiso 1 4 calc R . .
H21A H 0.10186 1.05916 0.3861 0.0679 Uiso 1 4 calc R . .
H21B H 0.18198 1.08092 0.42045 0.0679 Uiso 1 4 calc R . .
H21C H 0.12967 1.07469 0.46323 0.0679 Uiso 1 4 calc R . .
H24 H 0.45701 1.21641 0.21633 0.0739 Uiso 1 4 calc R . .
H25 H 0.53552 1.16369 0.31546 0.0832 Uiso 1 4 calc R . .
H26 H 0.51005 0.97863 0.38989 0.0729 Uiso 1 4 calc R . .
H28 H 0.28378 1.05949 0.16572 0.0561 Uiso 1 4 calc R . .
H29A H 0.32707 1.07052 0.06812 0.0931 Uiso 1 4 calc R . .
H29B H 0.4003 1.02714 0.11695 0.0931 Uiso 1 4 calc R . .
H30A H 0.2846 0.80704 0.09194 0.0984 Uiso 1 4 calc R . .
H30B H 0.35556 0.76463 0.14488 0.0984 Uiso 1 4 calc R . .
H30C H 0.35176 0.77179 0.06976 0.0984 Uiso 1 4 calc R . .
H31A H 0.321 1.36026 0.19483 0.0767 Uiso 1 4 calc R . .
H31B H 0.36395 1.34609 0.14368 0.0767 Uiso 1 4 calc R . .
H32A H 0.21956 1.31382 0.11047 0.0943 Uiso 1 4 calc R . .
H32B H 0.2634 1.30757 0.05978 0.0943 Uiso 1 4 calc R . .
H32C H 0.25903 1.48517 0.09784 0.0943 Uiso 1 4 calc R . .
H33 H 0.35056 0.75723 0.36992 0.0742 Uiso 1 4 calc R . .
H34A H 0.44462 0.59168 0.34269 0.1070 Uiso 1 4 calc R . .
H34B H 0.49259 0.64597 0.4123 0.1070 Uiso 1 4 calc R . .
H35A H 0.38002 0.42677 0.38729 0.1669 Uiso 1 4 calc R . .
H35B H 0.42151 0.4919 0.45822 0.1669 Uiso 1 4 calc R . .
H35C H 0.4585 0.37314 0.41714 0.1669 Uiso 1 4 calc R . .
H36A H 0.45768 0.91418 0.46772 0.0988 Uiso 1 4 calc R . .
H36B H 0.40566 0.77406 0.48199 0.0988 Uiso 1 4 calc R . .
H37A H 0.31443 0.9712 0.43769 0.1133 Uiso 1 4 calc R . .
H37B H 0.36866 1.11253 0.42831 0.1133 Uiso 1 4 calc R . .
H37C H 0.3693 1.05216 0.49956 0.1133 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Se1 C1 1.829(3) yes . .
N2 C1 1.366(3) yes . .
N2 C3 1.386(4) yes . .
N2 C6 1.445(4) yes . .
N5 C1 1.363(4) yes . .
N5 C4 1.388(4) yes . .
N5 C22 1.447(4) yes . .
C3 C4 1.329(4) yes . .
C6 C7 1.398(3) yes . .
C6 C11 1.396(4) yes . .
C7 C8 1.395(4) yes . .
C7 C12 1.519(4) yes . .
C8 C9 1.378(5) yes . .
C9 C10 1.382(4) yes . .
C10 C11 1.389(4) yes . .
C11 C17 1.522(3) yes . .
C12 C13 1.531(4) yes . .
C12 C15 1.537(4) yes . .
C13 C14 1.521(4) yes . .
C15 C16 1.514(5) yes . .
C17 C18 1.546(4) yes . .
C17 C20 1.541(5) yes . .
C18 C19 1.510(4) yes . .
C20 C21 1.508(5) yes . .
C22 C23 1.387(5) yes . .
C22 C27 1.405(4) yes . .
C23 C24 1.403(5) yes . .
C23 C28 1.522(4) yes . .
C24 C25 1.373(5) yes . .
C25 C26 1.371(6) yes . .
C26 C27 1.387(5) yes . .
C27 C33 1.522(6) yes . .
C28 C29 1.562(6) yes . .
C28 C31 1.524(5) yes . .
C29 C30 1.480(7) yes . .
C31 C32 1.501(5) yes . .
C33 C34 1.612(7) yes . .
C33 C36 1.495(6) yes . .
C34 C35 1.418(9) yes . .
C36 C37 1.505(8) yes . .
C3 H3 0.950 no . .
C4 H4 0.950 no . .
C8 H8 0.950 no . .
C9 H9 0.950 no . .
C10 H10 0.950 no . .
C12 H12 1.000 no . .
C13 H13A 0.990 no . .
C13 H13B 0.990 no . .
C14 H14A 0.980 no . .
C14 H14B 0.980 no . .
C14 H14C 0.980 no . .
C15 H15A 0.990 no . .
C15 H15B 0.990 no . .
C16 H16A 0.980 no . .
C16 H16B 0.980 no . .
C16 H16C 0.980 no . .
C17 H17 1.000 no . .
C18 H18A 0.990 no . .
C18 H18B 0.990 no . .
C19 H19A 0.980 no . .
C19 H19B 0.980 no . .
C19 H19C 0.980 no . .
C20 H20A 0.990 no . .
C20 H20B 0.990 no . .
C21 H21A 0.980 no . .
C21 H21B 0.980 no . .
C21 H21C 0.980 no . .
C24 H24 0.950 no . .
C25 H25 0.950 no . .
C26 H26 0.950 no . .
C28 H28 1.000 no . .
C29 H29A 0.990 no . .
C29 H29B 0.990 no . .
C30 H30A 0.980 no . .
C30 H30B 0.980 no . .
C30 H30C 0.980 no . .
C31 H31A 0.990 no . .
C31 H31B 0.990 no . .
C32 H32A 0.980 no . .
C32 H32B 0.980 no . .
C32 H32C 0.980 no . .
C33 H33 1.000 no . .
C34 H34A 0.990 no . .
C34 H34B 0.990 no . .
C35 H35A 0.980 no . .
C35 H35B 0.980 no . .
C35 H35C 0.980 no . .
C36 H36A 0.990 no . .
C36 H36B 0.990 no . .
C37 H37A 0.980 no . .
C37 H37B 0.980 no . .
C37 H37C 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N2 C3 110.3(2) yes . . .
C1 N2 C6 125.9(2) yes . . .
C3 N2 C6 123.8(2) yes . . .
C1 N5 C4 110.0(2) yes . . .
C1 N5 C22 126.5(2) yes . . .
C4 N5 C22 123.3(2) yes . . .
Se1 C1 N2 127.8(2) yes . . .
Se1 C1 N5 127.45(19) yes . . .
N2 C1 N5 104.8(2) yes . . .
N2 C3 C4 107.2(2) yes . . .
N5 C4 C3 107.7(3) yes . . .
N2 C6 C7 118.2(3) yes . . .
N2 C6 C11 118.4(2) yes . . .
C7 C6 C11 123.2(3) yes . . .
C6 C7 C8 116.9(3) yes . . .
C6 C7 C12 123.0(2) yes . . .
C8 C7 C12 120.1(2) yes . . .
C7 C8 C9 121.4(2) yes . . .
C8 C9 C10 120.0(3) yes . . .
C9 C10 C11 121.4(3) yes . . .
C6 C11 C10 117.1(2) yes . . .
C6 C11 C17 121.3(3) yes . . .
C10 C11 C17 121.5(3) yes . . .
C7 C12 C13 111.5(2) yes . . .
C7 C12 C15 110.7(2) yes . . .
C13 C12 C15 112.5(2) yes . . .
C12 C13 C14 114.2(2) yes . . .
C12 C15 C16 113.5(3) yes . . .
C11 C17 C18 109.5(2) yes . . .
C11 C17 C20 113.4(2) yes . . .
C18 C17 C20 111.4(2) yes . . .
C17 C18 C19 114.2(2) yes . . .
C17 C20 C21 113.8(3) yes . . .
N5 C22 C23 119.0(2) yes . . .
N5 C22 C27 117.7(3) yes . . .
C23 C22 C27 123.2(3) yes . . .
C22 C23 C24 116.9(3) yes . . .
C22 C23 C28 124.1(3) yes . . .
C24 C23 C28 119.0(3) yes . . .
C23 C24 C25 120.8(4) yes . . .
C24 C25 C26 121.0(4) yes . . .
C25 C26 C27 120.9(3) yes . . .
C22 C27 C26 117.1(3) yes . . .
C22 C27 C33 123.6(3) yes . . .
C26 C27 C33 119.2(3) yes . . .
C23 C28 C29 110.7(3) yes . . .
C23 C28 C31 111.0(3) yes . . .
C29 C28 C31 111.2(3) yes . . .
C28 C29 C30 114.2(4) yes . . .
C28 C31 C32 114.3(3) yes . . .
C27 C33 C34 108.8(4) yes . . .
C27 C33 C36 114.3(4) yes . . .
C34 C33 C36 111.8(3) yes . . .
C33 C34 C35 117.0(5) yes . . .
C33 C36 C37 113.7(3) yes . . .
N2 C3 H3 126.402 no . . .
C4 C3 H3 126.380 no . . .
N5 C4 H4 126.122 no . . .
C3 C4 H4 126.139 no . . .
C7 C8 H8 119.293 no . . .
C9 C8 H8 119.288 no . . .
C8 C9 H9 120.029 no . . .
C10 C9 H9 120.018 no . . .
C9 C10 H10 119.291 no . . .
C11 C10 H10 119.301 no . . .
C7 C12 H12 107.301 no . . .
C13 C12 H12 107.305 no . . .
C15 C12 H12 107.306 no . . .
C12 C13 H13A 108.697 no . . .
C12 C13 H13B 108.702 no . . .
C14 C13 H13A 108.693 no . . .
C14 C13 H13B 108.702 no . . .
H13A C13 H13B 107.624 no . . .
C13 C14 H14A 109.471 no . . .
C13 C14 H14B 109.472 no . . .
C13 C14 H14C 109.466 no . . .
H14A C14 H14B 109.476 no . . .
H14A C14 H14C 109.463 no . . .
H14B C14 H14C 109.479 no . . .
C12 C15 H15A 108.864 no . . .
C12 C15 H15B 108.866 no . . .
C16 C15 H15A 108.862 no . . .
C16 C15 H15B 108.856 no . . .
H15A C15 H15B 107.718 no . . .
C15 C16 H16A 109.476 no . . .
C15 C16 H16B 109.481 no . . .
C15 C16 H16C 109.473 no . . .
H16A C16 H16B 109.465 no . . .
H16A C16 H16C 109.464 no . . .
H16B C16 H16C 109.468 no . . .
C11 C17 H17 107.431 no . . .
C18 C17 H17 107.430 no . . .
C20 C17 H17 107.421 no . . .
C17 C18 H18A 108.710 no . . .
C17 C18 H18B 108.692 no . . .
C19 C18 H18A 108.708 no . . .
C19 C18 H18B 108.707 no . . .
H18A C18 H18B 107.615 no . . .
C18 C19 H19A 109.471 no . . .
C18 C19 H19B 109.470 no . . .
C18 C19 H19C 109.465 no . . .
H19A C19 H19B 109.478 no . . .
H19A C19 H19C 109.475 no . . .
H19B C19 H19C 109.468 no . . .
C17 C20 H20A 108.803 no . . .
C17 C20 H20B 108.809 no . . .
C21 C20 H20A 108.796 no . . .
C21 C20 H20B 108.799 no . . .
H20A C20 H20B 107.664 no . . .
C20 C21 H21A 109.472 no . . .
C20 C21 H21B 109.470 no . . .
C20 C21 H21C 109.468 no . . .
H21A C21 H21B 109.482 no . . .
H21A C21 H21C 109.469 no . . .
H21B C21 H21C 109.466 no . . .
C23 C24 H24 119.618 no . . .
C25 C24 H24 119.630 no . . .
C24 C25 H25 119.473 no . . .
C26 C25 H25 119.484 no . . .
C25 C26 H26 119.515 no . . .
C27 C26 H26 119.545 no . . .
C23 C28 H28 107.935 no . . .
C29 C28 H28 107.938 no . . .
C31 C28 H28 107.940 no . . .
C28 C29 H29A 108.712 no . . .
C28 C29 H29B 108.705 no . . .
C30 C29 H29A 108.726 no . . .
C30 C29 H29B 108.718 no . . .
H29A C29 H29B 107.626 no . . .
C29 C30 H30A 109.476 no . . .
C29 C30 H30B 109.479 no . . .
C29 C30 H30C 109.465 no . . .
H30A C30 H30B 109.488 no . . .
H30A C30 H30C 109.458 no . . .
H30B C30 H30C 109.461 no . . .
C28 C31 H31A 108.682 no . . .
C28 C31 H31B 108.678 no . . .
C32 C31 H31A 108.674 no . . .
C32 C31 H31B 108.687 no . . .
H31A C31 H31B 107.613 no . . .
C31 C32 H32A 109.473 no . . .
C31 C32 H32B 109.464 no . . .
C31 C32 H32C 109.468 no . . .
H32A C32 H32B 109.470 no . . .
H32A C32 H32C 109.480 no . . .
H32B C32 H32C 109.471 no . . .
C27 C33 H33 107.205 no . . .
C34 C33 H33 107.202 no . . .
C36 C33 H33 107.192 no . . .
C33 C34 H34A 108.041 no . . .
C33 C34 H34B 108.041 no . . .
C35 C34 H34A 108.036 no . . .
C35 C34 H34B 108.041 no . . .
H34A C34 H34B 107.255 no . . .
C34 C35 H35A 109.471 no . . .
C34 C35 H35B 109.471 no . . .
C34 C35 H35C 109.470 no . . .
H35A C35 H35B 109.472 no . . .
H35A C35 H35C 109.472 no . . .
H35B C35 H35C 109.472 no . . .
C33 C36 H36A 108.823 no . . .
C33 C36 H36B 108.825 no . . .
C37 C36 H36A 108.830 no . . .
C37 C36 H36B 108.833 no . . .
H36A C36 H36B 107.690 no . . .
C36 C37 H37A 109.467 no . . .
C36 C37 H37B 109.476 no . . .
C36 C37 H37C 109.463 no . . .
H37A C37 H37B 109.476 no . . .
H37A C37 H37C 109.471 no . . .
H37B C37 H37C 109.475 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N2 C3 C4 0.3(3) no . . . .
C3 N2 C1 Se1 -178.84(19) no . . . .
C3 N2 C1 N5 0.0(3) no . . . .
C1 N2 C6 C7 97.2(3) no . . . .
C1 N2 C6 C11 -86.5(3) no . . . .
C6 N2 C1 Se1 -0.1(4) no . . . .
C6 N2 C1 N5 178.8(2) no . . . .
C3 N2 C6 C7 -84.2(3) no . . . .
C3 N2 C6 C11 92.1(3) no . . . .
C6 N2 C3 C4 -178.6(2) no . . . .
C1 N5 C4 C3 0.5(3) no . . . .
C4 N5 C1 Se1 178.6(2) no . . . .
C4 N5 C1 N2 -0.3(3) no . . . .
C1 N5 C22 C23 -80.4(4) no . . . .
C1 N5 C22 C27 102.5(3) no . . . .
C22 N5 C1 Se1 4.6(4) no . . . .
C22 N5 C1 N2 -174.3(2) no . . . .
C4 N5 C22 C23 106.3(3) no . . . .
C4 N5 C22 C27 -70.7(4) no . . . .
C22 N5 C4 C3 174.7(2) no . . . .
N2 C3 C4 N5 -0.5(3) no . . . .
N2 C6 C7 C8 177.96(18) no . . . .
N2 C6 C7 C12 -1.6(3) no . . . .
N2 C6 C11 C10 -176.72(19) no . . . .
N2 C6 C11 C17 -1.0(3) no . . . .
C7 C6 C11 C10 -0.6(4) no . . . .
C7 C6 C11 C17 175.1(2) no . . . .
C11 C6 C7 C8 1.9(4) no . . . .
C11 C6 C7 C12 -177.7(2) no . . . .
C6 C7 C8 C9 -2.3(4) no . . . .
C6 C7 C12 C13 128.2(2) no . . . .
C6 C7 C12 C15 -105.8(3) no . . . .
C8 C7 C12 C13 -51.3(3) no . . . .
C8 C7 C12 C15 74.7(3) no . . . .
C12 C7 C8 C9 177.3(2) no . . . .
C7 C8 C9 C10 1.5(4) no . . . .
C8 C9 C10 C11 -0.2(4) no . . . .
C9 C10 C11 C6 -0.2(4) no . . . .
C9 C10 C11 C17 -175.9(2) no . . . .
C6 C11 C17 C18 -90.1(3) no . . . .
C6 C11 C17 C20 144.8(2) no . . . .
C10 C11 C17 C18 85.4(3) no . . . .
C10 C11 C17 C20 -39.7(3) no . . . .
C7 C12 C13 C14 -57.2(3) no . . . .
C7 C12 C15 C16 173.46(18) no . . . .
C13 C12 C15 C16 -61.1(3) no . . . .
C15 C12 C13 C14 177.8(2) no . . . .
C11 C17 C18 C19 165.4(2) no . . . .
C11 C17 C20 C21 -59.7(3) no . . . .
C18 C17 C20 C21 176.2(2) no . . . .
C20 C17 C18 C19 -68.4(3) no . . . .
N5 C22 C23 C24 -176.7(2) no . . . .
N5 C22 C23 C28 3.8(5) no . . . .
N5 C22 C27 C26 176.7(2) no . . . .
N5 C22 C27 C33 0.3(5) no . . . .
C23 C22 C27 C26 -0.2(5) no . . . .
C23 C22 C27 C33 -176.6(3) no . . . .
C27 C22 C23 C24 0.2(5) no . . . .
C27 C22 C23 C28 -179.3(3) no . . . .
C22 C23 C24 C25 -0.5(5) no . . . .
C22 C23 C28 C29 -107.7(4) no . . . .
C22 C23 C28 C31 128.3(3) no . . . .
C24 C23 C28 C29 72.7(4) no . . . .
C24 C23 C28 C31 -51.2(4) no . . . .
C28 C23 C24 C25 179.0(3) no . . . .
C23 C24 C25 C26 0.8(6) no . . . .
C24 C25 C26 C27 -0.8(7) no . . . .
C25 C26 C27 C22 0.5(6) no . . . .
C25 C26 C27 C33 177.1(3) no . . . .
C22 C27 C33 C34 107.4(3) no . . . .
C22 C27 C33 C36 -126.9(3) no . . . .
C26 C27 C33 C34 -69.0(4) no . . . .
C26 C27 C33 C36 56.8(5) no . . . .
C23 C28 C29 C30 77.2(4) no . . . .
C23 C28 C31 C32 -163.7(3) no . . . .
C29 C28 C31 C32 72.6(4) no . . . .
C31 C28 C29 C30 -159.0(3) no . . . .
C27 C33 C34 C35 -161.2(3) no . . . .
C27 C33 C36 C37 64.9(4) no . . . .
C34 C33 C36 C37 -170.9(3) no . . . .
C36 C33 C34 C35 71.6(5) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Se1 C6 3.345(2) no . .
Se1 C22 3.350(3) no . .
N2 C12 2.910(3) no . .
N2 C17 2.874(4) no . .
N2 C18 3.505(4) no . .
N2 C22 3.574(4) no . .
N5 C6 3.571(4) no . .
N5 C28 2.942(4) no . .
N5 C33 2.919(4) no . .
C1 C7 3.397(3) no . .
C1 C11 3.322(4) no . .
C1 C17 3.461(4) no . .
C1 C23 3.289(4) no . .
C1 C27 3.436(4) no . .
C1 C28 3.424(5) no . .
C3 C7 3.292(4) no . .
C3 C11 3.352(4) no . .
C3 C12 3.464(3) no . .
C3 C17 3.523(4) no . .
C3 C18 3.569(5) no . .
C3 C22 3.579(4) no . .
C4 C6 3.574(4) no . .
C4 C23 3.451(4) no . .
C4 C27 3.182(4) no . .
C4 C30 3.589(6) no . .
C4 C33 3.246(4) no . .
C6 C9 2.746(4) no . .
C6 C15 3.513(4) no . .
C6 C18 3.343(4) no . .
C7 C10 2.796(5) no . .
C7 C14 3.024(4) no . .
C8 C11 2.794(4) no . .
C8 C13 3.010(5) no . .
C8 C14 3.478(5) no . .
C8 C15 3.200(5) no . .
C10 C18 3.299(4) no . .
C10 C20 2.999(4) no . .
C10 C21 3.412(4) no . .
C11 C21 3.081(4) no . .
C13 C16 3.076(5) no . .
C19 C20 3.153(5) no . .
C22 C25 2.733(5) no . .
C22 C29 3.550(6) no . .
C22 C34 3.565(6) no . .
C23 C26 2.798(4) no . .
C23 C30 3.212(6) no . .
C24 C27 2.792(6) no . .
C24 C29 3.188(5) no . .
C24 C31 2.983(5) no . .
C26 C34 3.140(7) no . .
C26 C36 3.070(7) no . .
C27 C37 3.103(7) no . .
C29 C32 3.182(6) no . .
C35 C36 3.212(9) no . .
Se1 H15B 3.3536 no . .
Se1 H17 3.3865 no . .
Se1 H21B 3.3943 no . .
Se1 H28 3.1828 no . .
Se1 H31A 3.4584 no . .
N2 H4 3.1081 no . .
N2 H12 2.4144 no . .
N2 H15B 3.5258 no . .
N2 H17 2.4437 no . .
N2 H18B 3.0803 no . .
N2 H28 3.5413 no . .
N2 H33 3.4667 no . .
N5 H3 3.1166 no . .
N5 H12 3.5837 no . .
N5 H17 3.4224 no . .
N5 H28 2.4769 no . .
N5 H30A 3.5924 no . .
N5 H30B 3.1158 no . .
N5 H33 2.4191 no . .
C1 H3 3.1717 no . .
C1 H4 3.1657 no . .
C1 H12 3.0472 no . .
C1 H15B 3.5093 no . .
C1 H17 2.7159 no . .
C1 H28 2.6874 no . .
C1 H33 3.0350 no . .
C3 H12 2.7452 no . .
C3 H14B 3.3961 no . .
C3 H17 3.1103 no . .
C3 H18B 2.8695 no . .
C3 H33 3.2663 no . .
C4 H12 3.4439 no . .
C4 H28 3.3206 no . .
C4 H30A 3.4320 no . .
C4 H30B 2.9079 no . .
C4 H33 2.6140 no . .
C4 H34A 3.2581 no . .
C6 H3 2.7883 no . .
C6 H8 3.2428 no . .
C6 H10 3.2387 no . .
C6 H12 2.5955 no . .
C6 H14A 3.3690 no . .
C6 H15B 3.3192 no . .
C6 H17 2.6024 no . .
C6 H18B 3.0334 no . .
C7 H3 3.4171 no . .
C7 H9 3.2727 no . .
C7 H13A 2.7402 no . .
C7 H13B 3.3624 no . .
C7 H14A 2.6798 no . .
C7 H14B 3.3454 no . .
C7 H15A 2.7408 no . .
C7 H15B 2.6447 no . .
C8 H10 3.2431 no . .
C8 H12 3.3100 no . .
C8 H13A 2.7545 no . .
C8 H14A 2.9445 no . .
C8 H15A 2.9684 no . .
C8 H15B 3.4223 no . .
C10 H8 3.2438 no . .
C10 H17 3.3013 no . .
C10 H18A 3.1579 no . .
C10 H18B 3.4487 no . .
C10 H20A 2.7557 no . .
C10 H21A 2.8546 no . .
C11 H3 3.5320 no . .
C11 H9 3.2704 no . .
C11 H18A 2.7879 no . .
C11 H18B 2.5725 no . .
C11 H20A 2.7676 no . .
C11 H20B 3.3937 no . .
C11 H21A 2.7539 no . .
C11 H21B 3.3802 no . .
C12 H8 2.6667 no . .
C12 H14A 2.7525 no . .
C12 H14B 2.7763 no . .
C12 H14C 3.3926 no . .
C12 H16A 2.8030 no . .
C12 H16B 2.7001 no . .
C12 H16C 3.3837 no . .
C13 H8 2.8075 no . .
C13 H15A 2.7440 no . .
C13 H15B 3.3898 no . .
C13 H16A 2.8035 no . .
C13 H16B 3.3018 no . .
C14 H3 3.4736 no . .
C14 H8 3.4784 no . .
C14 H12 2.7432 no . .
C15 H8 3.1170 no . .
C15 H13A 2.7429 no . .
C15 H13B 2.7105 no . .
C15 H32A 3.4957 no . .
C16 H12 2.7076 no . .
C16 H13A 3.3875 no . .
C16 H13B 2.7046 no . .
C16 H32A 3.0336 no . .
C17 H10 2.6911 no . .
C17 H19A 2.7927 no . .
C17 H19B 2.7372 no . .
C17 H19C 3.3978 no . .
C17 H21A 2.7533 no . .
C17 H21B 2.7510 no . .
C17 H21C 3.3886 no . .
C17 H37A 3.4721 no . .
C18 H3 3.4859 no . .
C18 H10 3.3434 no . .
C18 H20A 2.7527 no . .
C18 H20B 2.6968 no . .
C19 H17 2.6757 no . .
C19 H20A 3.5094 no . .
C19 H20B 2.7870 no . .
C19 H33 3.5513 no . .
C19 H35A 3.3371 no . .
C20 H10 2.7038 no . .
C20 H18A 2.6860 no . .
C20 H18B 3.3875 no . .
C20 H19A 2.8611 no . .
C20 H19B 3.4607 no . .
C20 H37A 3.5361 no . .
C21 H10 3.2171 no . .
C21 H17 2.7290 no . .
C21 H37A 3.5311 no . .
C22 H4 2.7785 no . .
C22 H24 3.2409 no . .
C22 H26 3.2466 no . .
C22 H28 2.6207 no . .
C22 H30B 3.1419 no . .
C22 H31A 3.5476 no . .
C22 H33 2.6076 no . .
C22 H34A 3.3156 no . .
C22 H37B 3.4720 no . .
C23 H25 3.2676 no . .
C23 H29A 3.3581 no . .
C23 H29B 2.6155 no . .
C23 H30B 2.8942 no . .
C23 H31A 2.5719 no . .
C23 H31B 2.8087 no . .
C24 H26 3.2407 no . .
C24 H28 3.3176 no . .
C24 H29B 2.8181 no . .
C24 H31A 2.9749 no . .
C24 H31B 2.8296 no . .
C26 H24 3.2410 no . .
C26 H33 3.3021 no . .
C26 H34A 3.1788 no . .
C26 H34B 2.9955 no . .
C26 H36A 2.7598 no . .
C26 H37B 3.2594 no . .
C27 H4 3.2602 no . .
C27 H25 3.2519 no . .
C27 H34A 2.5809 no . .
C27 H34B 2.8528 no . .
C27 H36A 2.7058 no . .
C27 H36B 3.3673 no . .
C27 H37A 3.3875 no . .
C27 H37B 2.8123 no . .
C28 H24 2.6593 no . .
C28 H30A 2.7777 no . .
C28 H30B 2.7199 no . .
C28 H30C 3.3908 no . .
C28 H32A 2.7273 no . .
C28 H32B 2.7592 no . .
C28 H32C 3.3721 no . .
C29 H24 3.0971 no . .
C29 H31A 3.3818 no . .
C29 H31B 2.6446 no . .
C29 H32A 3.5339 no . .
C29 H32B 2.8819 no . .
C30 H4 3.4641 no . .
C30 H28 2.6293 no . .
C31 H24 2.7676 no . .
C31 H29A 2.5865 no . .
C31 H29B 2.8843 no . .
C32 H16B 3.3302 no . .
C32 H16C 3.3562 no . .
C32 H28 2.6371 no . .
C32 H29A 2.7691 no . .
C33 H4 3.3033 no . .
C33 H19B 3.3428 no . .
C33 H26 2.6463 no . .
C33 H35A 2.8230 no . .
C33 H35B 2.7376 no . .
C33 H35C 3.4190 no . .
C33 H37A 2.6905 no . .
C33 H37B 2.7423 no . .
C33 H37C 3.3416 no . .
C34 H4 3.3220 no . .
C34 H26 3.0467 no . .
C34 H36A 2.8057 no . .
C34 H36B 2.6677 no . .
C35 H19B 3.1137 no . .
C35 H33 2.7077 no . .
C35 H36B 2.8488 no . .
C36 H19B 3.5260 no . .
C36 H26 2.8667 no . .
C36 H34A 3.3866 no . .
C36 H34B 2.6962 no . .
C36 H35B 2.8838 no . .
C37 H17 3.5890 no . .
C37 H21B 3.5638 no . .
C37 H33 2.6435 no . .
H3 H4 2.4527 no . .
H3 H12 2.9988 no . .
H3 H14A 3.2782 no . .
H3 H14B 2.8596 no . .
H3 H17 3.5767 no . .
H3 H18B 2.6096 no . .
H4 H30A 3.4796 no . .
H4 H30B 2.6297 no . .
H4 H33 2.8582 no . .
H4 H34A 2.6976 no . .
H4 H35A 3.2809 no . .
H8 H9 2.3184 no . .
H8 H12 3.5982 no . .
H8 H13A 2.2621 no . .
H8 H14A 3.0910 no . .
H8 H15A 2.6438 no . .
H8 H15B 3.5347 no . .
H9 H10 2.3223 no . .
H10 H17 3.5827 no . .
H10 H18A 2.9850 no . .
H10 H20A 2.1764 no . .
H10 H21A 2.7614 no . .
H12 H13A 2.8609 no . .
H12 H13B 2.3542 no . .
H12 H14A 3.0293 no . .
H12 H14B 2.5898 no . .
H12 H15A 2.8672 no . .
H12 H15B 2.3812 no . .
H12 H16A 3.0741 no . .
H12 H16B 2.4814 no . .
H12 H16C 3.5677 no . .
H12 H28 3.3408 no . .
H12 H30A 3.2690 no . .
H13A H14A 2.3747 no . .
H13A H14B 2.8546 no . .
H13A H14C 2.3385 no . .
H13A H15A 2.5669 no . .
H13A H16A 3.0087 no . .
H13B H14A 2.8552 no . .
H13B H14B 2.3557 no . .
H13B H14C 2.3572 no . .
H13B H15A 2.9920 no . .
H13B H16A 2.2239 no . .
H13B H16B 2.8543 no . .
H15A H16A 2.3214 no . .
H15A H16B 2.8504 no . .
H15A H16C 2.3858 no . .
H15B H16A 2.8483 no . .
H15B H16B 2.4023 no . .
H15B H16C 2.3066 no . .
H15B H28 3.4758 no . .
H15B H32A 2.9472 no . .
H16B H28 3.0514 no . .
H16B H29A 3.4293 no . .
H16B H30A 2.9909 no . .
H16B H32A 2.7292 no . .
H16B H32B 3.0782 no . .
H16C H32A 2.6427 no . .
H16C H32B 3.2372 no . .
H17 H18A 2.8693 no . .
H17 H18B 2.4351 no . .
H17 H19A 2.9745 no . .
H17 H19B 2.4746 no . .
H17 H19C 3.5656 no . .
H17 H20A 2.8706 no . .
H17 H20B 2.3731 no . .
H17 H21A 3.0264 no . .
H17 H21B 2.5555 no . .
H17 H33 2.9478 no . .
H17 H37A 2.6475 no . .
H18A H19A 2.3335 no . .
H18A H19B 2.8467 no . .
H18A H19C 2.3595 no . .
H18A H20A 2.5187 no . .
H18A H20B 2.8860 no . .
H18B H19A 2.8456 no . .
H18B H19B 2.3776 no . .
H18B H19C 2.3167 no . .
H18B H20A 3.5969 no . .
H19A H20A 3.1696 no . .
H19A H20B 2.2516 no . .
H19B H20B 3.0702 no . .
H19B H33 2.6105 no . .
H19B H35A 2.5955 no . .
H19B H35B 2.8397 no . .
H19B H36B 3.0476 no . .
H19B H37A 3.2598 no . .
H19C H35A 3.2236 no . .
H20A H21A 2.3537 no . .
H20A H21B 2.8465 no . .
H20A H21C 2.3391 no . .
H20B H21A 2.8465 no . .
H20B H21B 2.3556 no . .
H20B H21C 2.3372 no . .
H20B H37A 3.1934 no . .
H21B H37A 2.7545 no . .
H24 H25 2.3105 no . .
H24 H28 3.5971 no . .
H24 H29B 2.5686 no . .
H24 H31A 2.8991 no . .
H24 H31B 2.3112 no . .
H25 H26 2.3067 no . .
H26 H33 3.5856 no . .
H26 H34A 3.2812 no . .
H26 H34B 2.6280 no . .
H26 H36A 2.2876 no . .
H26 H37B 3.3837 no . .
H28 H29A 2.5072 no . .
H28 H29B 2.8759 no . .
H28 H30A 2.5019 no . .
H28 H30B 2.7921 no . .
H28 H30C 3.5610 no . .
H28 H31A 2.4431 no . .
H28 H31B 2.8532 no . .
H28 H32A 2.4522 no . .
H28 H32B 2.9037 no . .
H28 H32C 3.5398 no . .
H29A H30A 2.3058 no . .
H29A H30B 2.8244 no . .
H29A H30C 2.3333 no . .
H29A H31A 3.5448 no . .
H29A H31B 2.6349 no . .
H29A H32A 3.2029 no . .
H29A H32B 2.2055 no . .
H29A H32C 3.5876 no . .
H29B H30A 2.8233 no . .
H29B H30B 2.3513 no . .
H29B H30C 2.2889 no . .
H29B H31B 2.6563 no . .
H29B H32B 3.4567 no . .
H31A H32A 2.3598 no . .
H31A H32B 2.8393 no . .
H31A H32C 2.3168 no . .
H31B H32A 2.8402 no . .
H31B H32B 2.3344 no . .
H31B H32C 2.3420 no . .
H33 H34A 2.5064 no . .
H33 H34B 2.9082 no . .
H33 H35A 2.5953 no . .
H33 H35B 2.8715 no . .
H33 H36A 2.8331 no . .
H33 H36B 2.3587 no . .
H33 H37A 2.4426 no . .
H33 H37B 2.9681 no . .
H33 H37C 3.5234 no . .
H34A H35A 2.2315 no . .
H34A H35B 2.7719 no . .
H34A H35C 2.2757 no . .
H34B H35A 2.7694 no . .
H34B H35B 2.3016 no . .
H34B H35C 2.2078 no . .
H34B H36A 2.5723 no . .
H34B H36B 2.8106 no . .
H35A H36B 3.2950 no . .
H35B H36A 3.3000 no . .
H35B H36B 2.2585 no . .
H36A H37A 2.8442 no . .
H36A H37B 2.3316 no . .
H36A H37C 2.3564 no . .
H36B H37A 2.3729 no . .
H36B H37B 2.8432 no . .
H36B H37C 2.3157 no . .
Se1 H3 3.0116 no . 1_565
Se1 H9 3.4102 no . 2_555
Se1 H18B 3.1031 no . 1_565
Se1 H19C 3.5762 no . 1_565
C3 H31A 3.2111 no . 1_545
C3 H32C 3.5325 no . 1_545
C4 H31A 2.8631 no . 1_545
C4 H32C 3.4638 no . 1_545
C8 H10 3.4717 no . 2_555
C8 H18A 3.2283 no . 2_555
C8 H21A 3.0768 no . 2_545
C9 H14A 3.2876 no . 2_555
C9 H21A 3.4219 no . 2_545
C10 H8 3.5537 no . 2_545
C10 H14A 3.0593 no . 2_555
C10 H15A 3.5242 no . 2_545
C13 H14C 3.2451 no . 3_565
C13 H16C 3.5471 no . 3_575
C13 H20A 3.4681 no . 4_564
C14 H10 3.2195 no . 2_545
C14 H14C 3.5330 no . 3_565
C14 H15A 3.5575 no . 1_545
C14 H15B 3.2718 no . 1_545
C14 H16C 3.1151 no . 1_545
C14 H21A 3.5683 no . 2_545
C14 H21C 3.5596 no . 4_564
C14 H32A 3.4262 no . 1_545
C15 H10 3.3686 no . 2_555
C15 H14B 3.5469 no . 1_565
C15 H14C 3.3062 no . 1_565
C15 H16A 3.4700 no . 3_575
C16 H13A 3.2027 no . 3_575
C16 H14B 3.5229 no . 1_565
C16 H14C 3.3217 no . 1_565
C16 H15A 3.5507 no . 3_575
C16 H18A 3.4580 no . 4_564
C16 H19A 3.4150 no . 4_564
C16 H20A 3.4648 no . 4_564
C16 H21C 3.3679 no . 4_574
C18 H8 3.3177 no . 2_545
C18 H9 3.5987 no . 2_545
C19 H16B 3.4569 no . 4_565
C19 H21B 3.3881 no . 1_545
C19 H29A 3.0098 no . 4_565
C19 H32B 3.5367 no . 4_565
C20 H13B 3.1613 no . 4_565
C20 H16A 3.4621 no . 4_565
C21 H8 3.3380 no . 2_555
C21 H13A 3.4133 no . 2_555
C21 H16C 3.3996 no . 4_575
C21 H19C 3.3595 no . 1_565
C21 H32B 3.5008 no . 4_575
C24 H34A 3.3770 no . 2_655
C25 H24 3.2525 no . 2_645
C25 H30B 3.2175 no . 2_655
C25 H31B 3.4727 no . 2_645
C25 H35C 3.3578 no . 1_565
C26 H24 3.1074 no . 2_645
C26 H31B 3.4263 no . 2_645
C26 H35C 3.2671 no . 1_565
C27 H24 3.5357 no . 2_645
C29 H19A 3.1950 no . 4_564
C29 H25 3.5995 no . 2_645
C29 H34B 3.5225 no . 2_655
C30 H19A 3.1037 no . 4_564
C30 H25 2.9910 no . 2_645
C30 H32C 2.9857 no . 1_545
C30 H36B 3.4263 no . 4_564
C31 H4 3.0164 no . 1_565
C32 H3 3.5354 no . 1_565
C32 H4 3.5611 no . 1_565
C32 H14B 3.1731 no . 1_565
C32 H21C 3.4213 no . 4_574
C32 H30A 3.4820 no . 1_565
C32 H37C 3.5991 no . 4_574
C34 H24 3.4903 no . 2_645
C34 H29B 3.2699 no . 2_645
C35 H35B 3.5436 no . 3_666
C35 H37B 2.9769 no . 1_545
C36 H26 3.5256 no . 3_676
C36 H30C 3.2803 no . 4_565
C36 H36A 3.2138 no . 3_676
C37 H19C 3.5692 no . 1_565
C37 H30C 3.3516 no . 4_565
C37 H35A 3.5364 no . 1_565
H3 Se1 3.0116 no . 1_545
H3 C32 3.5354 no . 1_545
H3 H31A 2.9293 no . 1_545
H3 H32A 3.1504 no . 1_545
H3 H32C 3.3370 no . 1_545
H4 C31 3.0164 no . 1_545
H4 C32 3.5611 no . 1_545
H4 H25 3.3945 no . 2_645
H4 H31A 2.1608 no . 1_545
H4 H31B 3.1804 no . 1_545
H4 H32C 3.2040 no . 1_545
H8 C10 3.5537 no . 2_555
H8 C18 3.3177 no . 2_555
H8 C21 3.3380 no . 2_545
H8 H10 3.2623 no . 2_555
H8 H16A 3.4453 no . 3_575
H8 H18A 2.4554 no . 2_555
H8 H18B 3.3598 no . 2_555
H8 H21A 2.5836 no . 2_545
H8 H21C 3.3600 no . 2_545
H9 Se1 3.4102 no . 2_545
H9 C18 3.5987 no . 2_555
H9 H14A 2.9873 no . 2_555
H9 H15B 3.3755 no . 2_545
H9 H18A 3.2794 no . 2_555
H9 H18B 2.9879 no . 2_555
H9 H21A 3.2239 no . 2_545
H10 C8 3.4717 no . 2_545
H10 C14 3.2195 no . 2_555
H10 C15 3.3686 no . 2_545
H10 H8 3.2623 no . 2_545
H10 H14A 2.5368 no . 2_555
H10 H14C 3.0428 no . 2_555
H10 H15A 2.6874 no . 2_545
H10 H15B 3.1442 no . 2_545
H13A C16 3.2027 no . 3_575
H13A C21 3.4133 no . 2_545
H13A H14C 2.9412 no . 3_565
H13A H15A 3.5794 no . 3_575
H13A H16A 2.8731 no . 3_575
H13A H16C 2.6918 no . 3_575
H13A H21A 3.0057 no . 2_545
H13A H21C 2.9141 no . 2_545
H13B C20 3.1613 no . 4_564
H13B H14C 2.8569 no . 3_565
H13B H15A 3.3903 no . 3_575
H13B H16C 3.5428 no . 3_575
H13B H20A 2.4827 no . 4_564
H13B H20B 3.0878 no . 4_564
H13B H21C 3.1726 no . 4_564
H14A C9 3.2876 no . 2_545
H14A C10 3.0593 no . 2_545
H14A H9 2.9873 no . 2_545
H14A H10 2.5368 no . 2_545
H14A H15A 3.5219 no . 1_545
H14A H15B 3.2055 no . 1_545
H14A H20A 3.5379 no . 2_545
H14A H21A 3.0803 no . 2_545
H14B C15 3.5469 no . 1_545
H14B C16 3.5229 no . 1_545
H14B C32 3.1731 no . 1_545
H14B H15B 2.9646 no . 1_545
H14B H16C 2.7757 no . 1_545
H14B H21C 3.2140 no . 4_564
H14B H32A 2.4873 no . 1_545
H14B H32C 3.0069 no . 1_545
H14C C13 3.2451 no . 3_565
H14C C14 3.5330 no . 3_565
H14C C15 3.3062 no . 1_545
H14C C16 3.3217 no . 1_545
H14C H10 3.0428 no . 2_545
H14C H13A 2.9412 no . 3_565
H14C H13B 2.8569 no . 3_565
H14C H14C 2.8953 no . 3_565
H14C H15A 2.9793 no . 1_545
H14C H15B 3.0959 no . 1_545
H14C H16C 2.5811 no . 1_545
H14C H20A 3.1674 no . 2_545
H14C H21A 3.4771 no . 2_545
H14C H21C 3.4820 no . 2_545
H14C H21C 3.2286 no . 4_564
H15A C10 3.5242 no . 2_555
H15A C14 3.5575 no . 1_565
H15A C16 3.5507 no . 3_575
H15A H10 2.6874 no . 2_555
H15A H13A 3.5794 no . 3_575
H15A H13B 3.3903 no . 3_575
H15A H14A 3.5219 no . 1_565
H15A H14C 2.9793 no . 1_565
H15A H16A 2.6524 no . 3_575
H15A H20A 3.2318 no . 2_555
H15B C14 3.2718 no . 1_565
H15B H9 3.3755 no . 2_555
H15B H10 3.1442 no . 2_555
H15B H14A 3.2055 no . 1_565
H15B H14B 2.9646 no . 1_565
H15B H14C 3.0959 no . 1_565
H16A C15 3.4700 no . 3_575
H16A C20 3.4621 no . 4_564
H16A H8 3.4453 no . 3_575
H16A H13A 2.8731 no . 3_575
H16A H15A 2.6524 no . 3_575
H16A H16A 3.2140 no . 3_575
H16A H18A 2.9700 no . 4_564
H16A H19A 3.4493 no . 4_564
H16A H20A 2.7190 no . 4_564
H16A H20B 3.3486 no . 4_564
H16B C19 3.4569 no . 4_564
H16B H18A 3.3396 no . 4_564
H16B H19A 2.6775 no . 4_564
H16B H20A 3.3443 no . 4_564
H16B H20B 3.1778 no . 4_564
H16B H21C 3.5974 no . 4_574
H16C C13 3.5471 no . 3_575
H16C C14 3.1151 no . 1_565
H16C C21 3.3996 no . 4_574
H16C H13A 2.6918 no . 3_575
H16C H13B 3.5428 no . 3_575
H16C H14B 2.7757 no . 1_565
H16C H14C 2.5811 no . 1_565
H16C H18A 3.5172 no . 4_564
H16C H21C 2.4970 no . 4_574
H18A C8 3.2283 no . 2_545
H18A C16 3.4580 no . 4_565
H18A H8 2.4554 no . 2_545
H18A H9 3.2794 no . 2_545
H18A H16A 2.9700 no . 4_565
H18A H16B 3.3396 no . 4_565
H18A H16C 3.5172 no . 4_565
H18A H21A 3.3960 no . 1_545
H18A H21B 3.3132 no . 1_545
H18A H21C 3.5789 no . 1_545
H18B Se1 3.1031 no . 1_545
H18B H8 3.3598 no . 2_545
H18B H9 2.9879 no . 2_545
H18B H21B 3.5996 no . 1_545
H19A C16 3.4150 no . 4_565
H19A C29 3.1950 no . 4_565
H19A C30 3.1037 no . 4_565
H19A H16A 3.4493 no . 4_565
H19A H16B 2.6775 no . 4_565
H19A H29A 2.4712 no . 4_565
H19A H30A 2.7009 no . 4_565
H19A H30C 3.0081 no . 4_565
H19A H32B 3.1943 no . 4_565
H19B H29A 3.1537 no . 4_565
H19B H30C 3.3670 no . 4_565
H19C Se1 3.5762 no . 1_545
H19C C21 3.3595 no . 1_545
H19C C37 3.5692 no . 1_545
H19C H21B 2.5422 no . 1_545
H19C H21C 3.4577 no . 1_545
H19C H29A 2.9345 no . 4_565
H19C H32B 2.9688 no . 4_565
H19C H37A 3.3647 no . 1_545
H19C H37B 3.2415 no . 1_545
H19C H37C 3.5171 no . 1_545
H20A C13 3.4681 no . 4_565
H20A C16 3.4648 no . 4_565
H20A H13B 2.4827 no . 4_565
H20A H14A 3.5379 no . 2_555
H20A H14C 3.1674 no . 2_555
H20A H15A 3.2318 no . 2_545
H20A H16A 2.7190 no . 4_565
H20A H16B 3.3443 no . 4_565
H20B H13B 3.0878 no . 4_565
H20B H16A 3.3486 no . 4_565
H20B H16B 3.1778 no . 4_565
H20B H30A 2.9733 no . 4_565
H20B H30C 3.5375 no . 4_565
H20B H32C 3.1991 no . 4_575
H21A C8 3.0768 no . 2_555
H21A C9 3.4219 no . 2_555
H21A C14 3.5683 no . 2_555
H21A H8 2.5836 no . 2_555
H21A H9 3.2239 no . 2_555
H21A H13A 3.0057 no . 2_555
H21A H14A 3.0803 no . 2_555
H21A H14C 3.4771 no . 2_555
H21A H18A 3.3960 no . 1_565
H21B C19 3.3881 no . 1_565
H21B H18A 3.3132 no . 1_565
H21B H18B 3.5996 no . 1_565
H21B H19C 2.5422 no . 1_565
H21B H32B 3.1068 no . 4_575
H21C C14 3.5596 no . 4_565
H21C C16 3.3679 no . 4_575
H21C C32 3.4213 no . 4_575
H21C H8 3.3600 no . 2_555
H21C H13A 2.9141 no . 2_555
H21C H13B 3.1726 no . 4_565
H21C H14B 3.2140 no . 4_565
H21C H14C 3.4820 no . 2_555
H21C H14C 3.2286 no . 4_565
H21C H16B 3.5974 no . 4_575
H21C H16C 2.4970 no . 4_575
H21C H18A 3.5789 no . 1_565
H21C H19C 3.4577 no . 1_565
H21C H32A 3.2915 no . 4_575
H21C H32B 3.0572 no . 4_575
H21C H32C 3.3498 no . 4_575
H24 C25 3.2525 no . 2_655
H24 C26 3.1074 no . 2_655
H24 C27 3.5357 no . 2_655
H24 C34 3.4903 no . 2_655
H24 H25 3.4940 no . 2_655
H24 H26 3.2540 no . 2_655
H24 H34A 2.8342 no . 2_655
H24 H34B 3.2681 no . 2_655
H25 C29 3.5995 no . 2_655
H25 C30 2.9910 no . 2_655
H25 H4 3.3945 no . 2_655
H25 H24 3.4940 no . 2_645
H25 H29B 3.2317 no . 2_655
H25 H30B 2.2774 no . 2_655
H25 H30C 2.9736 no . 2_655
H25 H31B 3.1360 no . 2_645
H25 H34A 3.5902 no . 2_655
H25 H35C 3.4377 no . 1_565
H26 C36 3.5256 no . 3_676
H26 H24 3.2540 no . 2_645
H26 H30C 3.5111 no . 2_655
H26 H31B 3.0404 no . 2_645
H26 H35C 3.2980 no . 1_565
H26 H36A 3.0611 no . 3_676
H26 H36B 3.3813 no . 3_676
H26 H37C 2.9061 no . 3_676
H29A C19 3.0098 no . 4_564
H29A H19A 2.4712 no . 4_564
H29A H19B 3.1537 no . 4_564
H29A H19C 2.9345 no . 4_564
H29A H35B 3.4912 no . 4_564
H29A H37C 3.4577 no . 4_574
H29B C34 3.2699 no . 2_655
H29B H25 3.2317 no . 2_645
H29B H34A 3.0757 no . 2_655
H29B H34B 2.6080 no . 2_655
H29B H35B 3.5741 no . 4_564
H29B H35C 3.3856 no . 2_655
H30A C32 3.4820 no . 1_545
H30A H19A 2.7009 no . 4_564
H30A H20B 2.9733 no . 4_564
H30A H32C 2.5225 no . 1_545
H30B C25 3.2175 no . 2_645
H30B H25 2.2774 no . 2_645
H30B H31A 3.4089 no . 1_545
H30B H31B 3.1997 no . 1_545
H30B H32C 2.8848 no . 1_545
H30C C36 3.2803 no . 4_564
H30C C37 3.3516 no . 4_564
H30C H19A 3.0081 no . 4_564
H30C H19B 3.3670 no . 4_564
H30C H20B 3.5375 no . 4_564
H30C H25 2.9736 no . 2_645
H30C H26 3.5111 no . 2_645
H30C H31B 3.5962 no . 1_545
H30C H32C 3.0660 no . 1_545
H30C H36B 2.4723 no . 4_564
H30C H37A 3.2994 no . 4_564
H30C H37C 2.9740 no . 4_564
H31A C3 3.2111 no . 1_565
H31A C4 2.8631 no . 1_565
H31A H3 2.9293 no . 1_565
H31A H4 2.1608 no . 1_565
H31A H30B 3.4089 no . 1_565
H31B C25 3.4727 no . 2_655
H31B C26 3.4263 no . 2_655
H31B H4 3.1804 no . 1_565
H31B H25 3.1360 no . 2_655
H31B H26 3.0404 no . 2_655
H31B H30B 3.1997 no . 1_565
H31B H30C 3.5962 no . 1_565
H31B H37C 3.2353 no . 4_574
H32A C14 3.4262 no . 1_565
H32A H3 3.1504 no . 1_565
H32A H14B 2.4873 no . 1_565
H32A H21C 3.2915 no . 4_574
H32B C19 3.5367 no . 4_564
H32B C21 3.5008 no . 4_574
H32B H19A 3.1943 no . 4_564
H32B H19C 2.9688 no . 4_564
H32B H21B 3.1068 no . 4_574
H32B H21C 3.0572 no . 4_574
H32B H37A 3.5275 no . 4_574
H32B H37C 3.0209 no . 4_574
H32C C3 3.5325 no . 1_565
H32C C4 3.4638 no . 1_565
H32C C30 2.9857 no . 1_565
H32C H3 3.3370 no . 1_565
H32C H4 3.2040 no . 1_565
H32C H14B 3.0069 no . 1_565
H32C H20B 3.1991 no . 4_574
H32C H21C 3.3498 no . 4_574
H32C H30A 2.5225 no . 1_565
H32C H30B 2.8848 no . 1_565
H32C H30C 3.0660 no . 1_565
H32C H37C 3.5195 no . 4_574
H34A C24 3.3770 no . 2_645
H34A H24 2.8342 no . 2_645
H34A H25 3.5902 no . 2_645
H34A H29B 3.0757 no . 2_645
H34B C29 3.5225 no . 2_645
H34B H24 3.2681 no . 2_645
H34B H29B 2.6080 no . 2_645
H34B H35B 3.0287 no . 3_666
H34B H35C 3.5268 no . 3_666
H35A C37 3.5364 no . 1_545
H35A H37B 2.5897 no . 1_545
H35B C35 3.5436 no . 3_666
H35B H29A 3.4912 no . 4_565
H35B H29B 3.5741 no . 4_565
H35B H34B 3.0287 no . 3_666
H35B H35B 3.1994 no . 3_666
H35B H35C 3.2430 no . 3_666
H35B H37B 3.0931 no . 1_545
H35C C25 3.3578 no . 1_545
H35C C26 3.2671 no . 1_545
H35C H25 3.4377 no . 1_545
H35C H26 3.2980 no . 1_545
H35C H29B 3.3856 no . 2_645
H35C H34B 3.5268 no . 3_666
H35C H35B 3.2430 no . 3_666
H35C H36A 3.3865 no . 3_666
H35C H36B 3.1993 no . 3_666
H35C H37B 2.7637 no . 1_545
H36A C36 3.2138 no . 3_676
H36A H26 3.0611 no . 3_676
H36A H35C 3.3865 no . 3_666
H36A H36A 2.2945 no . 3_676
H36A H36B 3.5916 no . 3_676
H36A H37C 3.4106 no . 3_676
H36B C30 3.4263 no . 4_565
H36B H26 3.3813 no . 3_676
H36B H30C 2.4723 no . 4_565
H36B H35C 3.1993 no . 3_666
H36B H36A 3.5916 no . 3_676
H37A H19C 3.3647 no . 1_565
H37A H30C 3.2994 no . 4_565
H37A H32B 3.5275 no . 4_575
H37B C35 2.9769 no . 1_565
H37B H19C 3.2415 no . 1_565
H37B H35A 2.5897 no . 1_565
H37B H35B 3.0931 no . 1_565
H37B H35C 2.7637 no . 1_565
H37C C32 3.5991 no . 4_575
H37C H19C 3.5171 no . 1_565
H37C H26 2.9061 no . 3_676
H37C H29A 3.4577 no . 4_575
H37C H30C 2.9740 no . 4_565
H37C H31B 3.2353 no . 4_575
H37C H32B 3.0209 no . 4_575
H37C H32C 3.5195 no . 4_575
H37C H36A 3.4106 no . 3_676

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_chemical_name_systematic        '[Se(IPent)]'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_[Se(IPrCl)]
_database_code_depnum_ccdc_archive 'CCDC 1024813'
_audit_update_record             
;
2014-09-17 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT601_SeIPrCl             
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        210 Ang3  
RESPONSE: No chemically sensible solvent models could be made of electron
  density in these void spaces.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C27 H34 Cl2 N2 Se'
_chemical_formula_moiety         'C27 H34 Cl2 N2 Se'
_chemical_formula_weight         536.44
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
_space_group_IT_number           15
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,+Y,-Z
3 -X,-Y,-Z
4 1/2+X,-Y,+Z
5 1/2+X,1/2+Y,1/2+Z
6 -X,1/2+Y,1/2-Z
7 1/2-X,1/2-Y,1/2-Z
8 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   17.366(3)
_cell_length_b                   9.4565(13)
_cell_length_c                   21.295(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.080(3)
_cell_angle_gamma                90.0000
_cell_volume                     3305.0(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5160
_cell_measurement_theta_min      2.02
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_crystal_density_diffrn    1.078
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112.00
_exptl_absorpt_coefficient_mu    1.312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_T_max  0.889

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            19230
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_theta_max         25.398
_diffrn_reflns_theta_min         2.380
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3026
_reflns_number_gt                2677
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.2293
_refine_ls_wR_factor_gt          0.2240
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3026
_refine_ls_number_parameters     151
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1423P)²+5.5523P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         2.49
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.75 0.50449(6) 0.5 0.0364(3) Uani 1 4 d . . .
Cl1 Cl 0.64530(7) 1.06180(12) 0.49063(7) 0.0432(4) Uani 1 8 d . . .
N2 N 0.6853(2) 0.7851(4) 0.49354(18) 0.0269(7) Uani 1 8 d . . .
C1 C 0.75 0.6981(6) 0.5 0.0271(12) Uani 1 4 d . . .
C3 C 0.7104(3) 0.9255(4) 0.4960(2) 0.0302(9) Uani 1 8 d . . .
C4 C 0.6032(3) 0.7397(5) 0.4858(2) 0.0269(9) Uani 1 8 d . . .
C5 C 0.5780(3) 0.7402(5) 0.5414(2) 0.0306(9) Uani 1 8 d . . .
C6 C 0.4987(3) 0.6970(5) 0.5328(3) 0.0373(11) Uani 1 8 d . . .
C7 C 0.4472(3) 0.6582(5) 0.4705(3) 0.0394(11) Uani 1 8 d . . .
C8 C 0.4733(3) 0.6618(5) 0.4162(3) 0.0380(11) Uani 1 8 d . . .
C9 C 0.5531(3) 0.7015(5) 0.4226(2) 0.0321(10) Uani 1 8 d . . .
C10 C 0.6347(3) 0.7849(6) 0.6098(2) 0.0413(12) Uani 1 8 d . . .
C11 C 0.5929(5) 0.8907(8) 0.6427(4) 0.070(2) Uani 1 8 d . . .
C12 C 0.6649(5) 0.6559(8) 0.6541(3) 0.0669(19) Uani 1 8 d . . .
C13 C 0.5819(3) 0.7030(6) 0.3627(2) 0.0403(11) Uani 1 8 d . . .
C14 C 0.5448(5) 0.8262(8) 0.3167(3) 0.070(2) Uani 1 8 d . . .
C15 C 0.5619(6) 0.5639(8) 0.3242(4) 0.069(2) Uani 1 8 d . . .
H6 H 0.47963 0.69423 0.56981 0.0448 Uiso 1 8 calc R . .
H7 H 0.39321 0.62857 0.46524 0.0473 Uiso 1 8 calc R . .
H8 H 0.4367 0.63699 0.37369 0.0456 Uiso 1 8 calc R . .
H10 H 0.68315 0.83269 0.60373 0.0496 Uiso 1 8 calc R . .
H11A H 0.56755 0.96589 0.61109 0.0842 Uiso 1 8 calc R . .
H11B H 0.63347 0.9319 0.68194 0.0842 Uiso 1 8 calc R . .
H11C H 0.55107 0.84181 0.6562 0.0842 Uiso 1 8 calc R . .
H12A H 0.69094 0.58955 0.63186 0.0803 Uiso 1 8 calc R . .
H12B H 0.61875 0.60939 0.66236 0.0803 Uiso 1 8 calc R . .
H12C H 0.70454 0.68579 0.6964 0.0803 Uiso 1 8 calc R . .
H13 H 0.64248 0.71498 0.37884 0.0483 Uiso 1 8 calc R . .
H14A H 0.5608 0.8203 0.27674 0.0836 Uiso 1 8 calc R . .
H14B H 0.56432 0.91557 0.33973 0.0836 Uiso 1 8 calc R . .
H14C H 0.48525 0.82212 0.3041 0.0836 Uiso 1 8 calc R . .
H15A H 0.59151 0.55925 0.29218 0.0834 Uiso 1 8 calc R . .
H15B H 0.50323 0.55893 0.30056 0.0834 Uiso 1 8 calc R . .
H15C H 0.5783 0.48446 0.3553 0.0834 Uiso 1 8 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Se1 C1 1.831(6) yes . .
Cl1 C3 1.693(5) yes . .
N2 C1 1.362(5) yes . .
N2 C3 1.393(5) yes . .
N2 C4 1.446(6) yes . .
C3 C3 1.331(7) yes . 2_656
C4 C5 1.391(8) yes . .
C4 C9 1.390(6) yes . .
C5 C6 1.391(7) yes . .
C5 C10 1.527(6) yes . .
C6 C7 1.385(7) yes . .
C7 C8 1.373(9) yes . .
C8 C9 1.398(7) yes . .
C9 C13 1.515(8) yes . .
C10 C11 1.533(11) yes . .
C10 C12 1.526(9) yes . .
C13 C14 1.523(9) yes . .
C13 C15 1.528(9) yes . .
C6 H6 0.950 no . .
C7 H7 0.950 no . .
C8 H8 0.950 no . .
C10 H10 1.000 no . .
C11 H11A 0.980 no . .
C11 H11B 0.980 no . .
C11 H11C 0.980 no . .
C12 H12A 0.980 no . .
C12 H12B 0.980 no . .
C12 H12C 0.980 no . .
C13 H13 1.000 no . .
C14 H14A 0.980 no . .
C14 H14B 0.980 no . .
C14 H14C 0.980 no . .
C15 H15A 0.980 no . .
C15 H15B 0.980 no . .
C15 H15C 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N2 C3 109.6(4) yes . . .
C1 N2 C4 125.6(4) yes . . .
C3 N2 C4 124.8(4) yes . . .
Se1 C1 N2 127.1(2) yes . . .
Se1 C1 N2 127.1(2) yes . . 2_656
N2 C1 N2 105.7(4) yes . . 2_656
Cl1 C3 N2 122.0(4) yes . . .
Cl1 C3 C3 130.4(4) yes . . 2_656
N2 C3 C3 107.6(4) yes . . 2_656
N2 C4 C5 118.3(4) yes . . .
N2 C4 C9 118.0(5) yes . . .
C5 C4 C9 123.6(4) yes . . .
C4 C5 C6 117.4(4) yes . . .
C4 C5 C10 122.0(4) yes . . .
C6 C5 C10 120.6(5) yes . . .
C5 C6 C7 120.4(6) yes . . .
C6 C7 C8 120.8(5) yes . . .
C7 C8 C9 120.9(4) yes . . .
C4 C9 C8 116.8(5) yes . . .
C4 C9 C13 122.5(4) yes . . .
C8 C9 C13 120.7(4) yes . . .
C5 C10 C11 111.2(5) yes . . .
C5 C10 C12 110.6(4) yes . . .
C11 C10 C12 111.0(5) yes . . .
C9 C13 C14 111.1(5) yes . . .
C9 C13 C15 111.3(5) yes . . .
C14 C13 C15 109.9(5) yes . . .
C5 C6 H6 119.814 no . . .
C7 C6 H6 119.809 no . . .
C6 C7 H7 119.588 no . . .
C8 C7 H7 119.583 no . . .
C7 C8 H8 119.545 no . . .
C9 C8 H8 119.532 no . . .
C5 C10 H10 107.945 no . . .
C11 C10 H10 107.935 no . . .
C12 C10 H10 107.946 no . . .
C10 C11 H11A 109.463 no . . .
C10 C11 H11B 109.477 no . . .
C10 C11 H11C 109.471 no . . .
H11A C11 H11B 109.473 no . . .
H11A C11 H11C 109.467 no . . .
H11B C11 H11C 109.476 no . . .
C10 C12 H12A 109.469 no . . .
C10 C12 H12B 109.472 no . . .
C10 C12 H12C 109.466 no . . .
H12A C12 H12B 109.477 no . . .
H12A C12 H12C 109.466 no . . .
H12B C12 H12C 109.477 no . . .
C9 C13 H13 108.131 no . . .
C14 C13 H13 108.143 no . . .
C15 C13 H13 108.137 no . . .
C13 C14 H14A 109.472 no . . .
C13 C14 H14B 109.464 no . . .
C13 C14 H14C 109.472 no . . .
H14A C14 H14B 109.471 no . . .
H14A C14 H14C 109.481 no . . .
H14B C14 H14C 109.469 no . . .
C13 C15 H15A 109.462 no . . .
C13 C15 H15B 109.478 no . . .
C13 C15 H15C 109.476 no . . .
H15A C15 H15B 109.465 no . . .
H15A C15 H15C 109.468 no . . .
H15B C15 H15C 109.478 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N2 C3 Cl1 -179.1(3) no . . . .
C1 N2 C3 C3 -0.0(5) no . . . 2_656
C3 N2 C1 Se1 -180.0(2) no . . . .
C3 N2 C1 N2 0.0(3) no . . . 2_656
C1 N2 C4 C5 99.5(4) no . . . .
C1 N2 C4 C9 -82.2(4) no . . . .
C4 N2 C1 Se1 0.4(5) no . . . .
C4 N2 C1 N2 -179.6(3) no . . . 2_656
C3 N2 C4 C5 -80.0(5) no . . . .
C3 N2 C4 C9 98.3(5) no . . . .
C4 N2 C3 Cl1 0.5(6) no . . . .
C4 N2 C3 C3 179.5(4) no . . . 2_656
Cl1 C3 C3 Cl1 -2.1(8) no . . 2_656 2_656
Cl1 C3 C3 N2 179.0(4) no . . 2_656 2_656
N2 C3 C3 Cl1 179.0(4) no . . 2_656 2_656
N2 C3 C3 N2 0.0(5) no . . 2_656 2_656
N2 C4 C5 C6 179.6(3) no . . . .
N2 C4 C5 C10 -1.0(6) no . . . .
N2 C4 C9 C8 -178.3(3) no . . . .
N2 C4 C9 C13 1.3(6) no . . . .
C5 C4 C9 C8 -0.1(6) no . . . .
C5 C4 C9 C13 179.5(4) no . . . .
C9 C4 C5 C6 1.4(6) no . . . .
C9 C4 C5 C10 -179.1(4) no . . . .
C4 C5 C6 C7 -1.2(6) no . . . .
C4 C5 C10 C11 131.8(4) no . . . .
C4 C5 C10 C12 -104.3(5) no . . . .
C6 C5 C10 C11 -48.7(6) no . . . .
C6 C5 C10 C12 75.1(6) no . . . .
C10 C5 C6 C7 179.3(4) no . . . .
C5 C6 C7 C8 -0.2(7) no . . . .
C6 C7 C8 C9 1.6(7) no . . . .
C7 C8 C9 C4 -1.4(7) no . . . .
C7 C8 C9 C13 179.0(4) no . . . .
C4 C9 C13 C14 -107.0(5) no . . . .
C4 C9 C13 C15 130.2(4) no . . . .
C8 C9 C13 C14 72.6(5) no . . . .
C8 C9 C13 C15 -50.2(6) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Se1 C4 3.321(4) no . .
Se1 C4 3.321(4) no . 2_656
Cl1 Cl1 3.5263(19) no . 2_656
Cl1 C4 3.126(4) no . .
Cl1 C5 3.551(5) no . .
N2 C4 3.578(6) no . 2_656
N2 C10 2.886(7) no . .
N2 C13 2.884(6) no . .
C1 C3 2.251(7) no . 2_656
C1 C4 2.498(5) no . 2_656
C1 C5 3.402(5) no . .
C1 C5 3.402(5) no . 2_656
C1 C9 3.275(4) no . .
C1 C9 3.275(4) no . 2_656
C1 C13 3.390(4) no . .
C1 C13 3.390(4) no . 2_656
C3 C4 3.591(6) no . 2_656
C3 C5 3.276(7) no . .
C3 C9 3.405(6) no . .
C3 C10 3.383(8) no . .
C4 C7 2.732(7) no . .
C4 C12 3.480(8) no . .
C4 C14 3.503(8) no . .
C5 C8 2.792(6) no . .
C6 C9 2.802(8) no . .
C6 C11 3.002(9) no . .
C6 C12 3.207(8) no . .
C8 C14 3.188(11) no . .
C8 C15 3.005(11) no . .
Cl1 C6 3.299(5) no . 3_676
Cl1 C7 3.339(5) no . 3_676
C6 Cl1 3.299(5) no . 3_676
C6 C7 3.495(7) no . 3_666
C6 C8 3.548(7) no . 3_666
C7 Cl1 3.339(5) no . 3_676
C7 C6 3.495(7) no . 3_666
C7 C7 3.519(7) no . 3_666
C8 C6 3.548(7) no . 3_666
Se1 H12A 3.3862 no . .
Se1 H12A 3.3862 no . 2_656
Se1 H13 3.3100 no . .
Se1 H13 3.3100 no . 2_656
Se1 H15C 3.5235 no . .
Se1 H15C 3.5235 no . 2_656
Cl1 H10 3.1451 no . .
Cl1 H11A 3.3898 no . .
Cl1 H14B 3.3558 no . .
N2 H10 2.4018 no . .
N2 H10 3.5780 no . 2_656
N2 H12A 3.4521 no . .
N2 H13 2.4023 no . .
N2 H13 3.3843 no . 2_656
N2 H14B 3.4882 no . .
C1 H10 3.0860 no . .
C1 H10 3.0860 no . 2_656
C1 H12A 3.4458 no . .
C1 H12A 3.4458 no . 2_656
C1 H13 2.6494 no . .
C1 H13 2.6494 no . 2_656
C3 H10 2.6385 no . .
C3 H10 3.3573 no . 2_656
C3 H13 3.1074 no . .
C3 H14B 3.4642 no . .
C4 H6 3.2412 no . .
C4 H8 3.2388 no . .
C4 H10 2.5944 no . .
C4 H12A 3.3039 no . .
C4 H13 2.5922 no . .
C4 H14B 3.3943 no . .
C4 H15C 3.5979 no . .
C5 H7 3.2626 no . .
C5 H11A 2.6394 no . .
C5 H11B 3.3593 no . .
C5 H11C 2.8047 no . .
C5 H12A 2.6674 no . .
C5 H12B 2.7338 no . .
C5 H12C 3.3532 no . .
C6 H8 3.2517 no . .
C6 H10 3.3208 no . .
C6 H11A 3.0613 no . .
C6 H11C 2.8367 no . .
C6 H12A 3.4682 no . .
C6 H12B 2.9815 no . .
C8 H6 3.2518 no . .
C8 H13 3.3228 no . .
C8 H14B 3.5479 no . .
C8 H14C 2.8916 no . .
C8 H15B 2.8487 no . .
C8 H15C 3.0597 no . .
C9 H7 3.2649 no . .
C9 H14A 3.3462 no . .
C9 H14B 2.7336 no . .
C9 H14C 2.6668 no . .
C9 H15A 3.3435 no . .
C9 H15B 2.8019 no . .
C9 H15C 2.6209 no . .
C10 H6 2.6862 no . .
C11 H6 2.7815 no . .
C11 H12A 3.3639 no . .
C11 H12B 2.7070 no . .
C11 H12C 2.7143 no . .
C12 H6 3.1516 no . .
C12 H11A 3.3588 no . .
C12 H11B 2.7707 no . .
C12 H11C 2.6577 no . .
C13 H8 2.6820 no . .
C14 H8 3.1121 no . .
C14 H15A 2.7538 no . .
C14 H15B 2.6202 no . .
C14 H15C 3.3387 no . .
C15 H8 2.7955 no . .
C15 H14A 2.6244 no . .
C15 H14B 3.3404 no . .
C15 H14C 2.7469 no . .
H6 H7 2.3263 no . .
H6 H11A 2.9709 no . .
H6 H11C 2.3193 no . .
H6 H12B 2.6929 no . .
H7 H8 2.3109 no . .
H8 H14C 2.6055 no . .
H8 H15B 2.3412 no . .
H8 H15C 2.9850 no . .
H10 H11A 2.4181 no . .
H10 H11B 2.3104 no . .
H10 H11C 2.8623 no . .
H10 H12A 2.3687 no . .
H10 H12B 2.8603 no . .
H10 H12C 2.3416 no . .
H10 H13 3.1324 no . 2_656
H11A H12B 3.5656 no . .
H11B H12B 3.0775 no . .
H11B H12C 2.6050 no . .
H11C H12A 3.5612 no . .
H11C H12B 2.4756 no . .
H11C H12C 2.9191 no . .
H12A H13 3.2029 no . 2_656
H12C H13 3.5333 no . 2_656
H13 H14A 2.3906 no . .
H13 H14B 2.3227 no . .
H13 H14C 2.8590 no . .
H13 H15A 2.3000 no . .
H13 H15B 2.8581 no . .
H13 H15C 2.4249 no . .
H14A H15A 2.5243 no . .
H14A H15B 2.7744 no . .
H14A H15C 3.5560 no . .
H14B H15A 3.5937 no . .
H14B H15B 3.5520 no . .
H14C H15A 3.1552 no . .
H14C H15B 2.5126 no . .
H14C H15C 3.5838 no . .
Se1 H7 3.0854 no . 3_666
Se1 H7 3.0854 no . 4_565
Cl1 H6 3.1402 no . 3_676
Cl1 H7 3.2116 no . 3_676
C5 H7 3.5323 no . 3_666
C6 H7 3.5996 no . 3_666
C6 H15C 3.5352 no . 3_666
C7 H12A 3.5461 no . 3_666
C8 H6 3.4544 no . 3_666
C8 H12A 3.5955 no . 3_666
C8 H12B 3.1912 no . 3_666
C11 H14B 3.4091 no . 3_676
C11 H14C 3.3923 no . 3_676
C11 H15A 3.2255 no . 8_565
C12 H8 3.2330 no . 3_666
C12 H12C 3.5778 no . 7_666
C14 H11A 3.4631 no . 3_676
C14 H15A 3.4993 no . 6_655
C14 H15B 3.2269 no . 6_655
C15 H6 3.5549 no . 3_666
C15 H14A 3.3882 no . 6_645
C15 H14C 3.4505 no . 6_645
H6 Cl1 3.1402 no . 3_676
H6 C8 3.4544 no . 3_666
H6 C15 3.5549 no . 3_666
H6 H8 3.4966 no . 3_666
H6 H15B 3.5921 no . 3_666
H6 H15C 2.7313 no . 3_666
H7 Se1 3.0854 no . 3_666
H7 Cl1 3.2116 no . 3_676
H7 C5 3.5323 no . 3_666
H7 C6 3.5996 no . 3_666
H7 H12A 2.9479 no . 3_666
H7 H12B 3.4816 no . 3_666
H8 C12 3.2330 no . 3_666
H8 H6 3.4966 no . 3_666
H8 H12A 3.0570 no . 3_666
H8 H12B 2.5420 no . 3_666
H11A C14 3.4631 no . 3_676
H11A H14B 3.0275 no . 3_676
H11A H14C 3.0338 no . 3_676
H11B H12C 3.3316 no . 7_666
H11B H14C 3.1860 no . 3_676
H11B H15A 2.6772 no . 8_565
H11C H14A 2.9469 no . 8_565
H11C H14B 3.0660 no . 3_676
H11C H14C 3.4002 no . 3_676
H11C H15A 2.9025 no . 8_565
H11C H15B 3.5625 no . 8_565
H12A C7 3.5461 no . 3_666
H12A C8 3.5955 no . 3_666
H12A H7 2.9479 no . 3_666
H12A H8 3.0570 no . 3_666
H12B C8 3.1912 no . 3_666
H12B H7 3.4816 no . 3_666
H12B H8 2.5420 no . 3_666
H12B H14A 2.9984 no . 8_565
H12B H15B 2.9560 no . 3_666
H12B H15C 3.4348 no . 3_666
H12C C12 3.5778 no . 7_666
H12C H11B 3.3316 no . 7_666
H12C H12C 2.6120 no . 7_666
H12C H14A 3.4574 no . 8_565
H14A C15 3.3882 no . 6_655
H14A H11C 2.9469 no . 8_564
H14A H12B 2.9984 no . 8_564
H14A H12C 3.4574 no . 8_564
H14A H15A 3.4232 no . 6_655
H14A H15B 2.8003 no . 6_655
H14A H15C 3.4221 no . 6_655
H14B C11 3.4091 no . 3_676
H14B H11A 3.0275 no . 3_676
H14B H11C 3.0660 no . 3_676
H14B H15A 3.4771 no . 6_655
H14B H15B 3.1381 no . 6_655
H14C C11 3.3923 no . 3_676
H14C C15 3.4505 no . 6_655
H14C H11A 3.0338 no . 3_676
H14C H11B 3.1860 no . 3_676
H14C H11C 3.4002 no . 3_676
H14C H15A 3.0368 no . 6_655
H14C H15B 3.2115 no . 6_655
H14C H15C 3.5564 no . 6_655
H15A C11 3.2255 no . 8_564
H15A C14 3.4993 no . 6_645
H15A H11B 2.6772 no . 8_564
H15A H11C 2.9025 no . 8_564
H15A H14A 3.4232 no . 6_645
H15A H14B 3.4771 no . 6_645
H15A H14C 3.0368 no . 6_645
H15B C14 3.2269 no . 6_645
H15B H6 3.5921 no . 3_666
H15B H11C 3.5625 no . 8_564
H15B H12B 2.9560 no . 3_666
H15B H14A 2.8003 no . 6_645
H15B H14B 3.1381 no . 6_645
H15B H14C 3.2115 no . 6_645
H15C C6 3.5352 no . 3_666
H15C H6 2.7313 no . 3_666
H15C H12B 3.4348 no . 3_666
H15C H14A 3.4221 no . 6_645
H15C H14C 3.5564 no . 6_645

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_chemical_name_systematic        '[Se(IPrCl)]'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone, pentane'
####################################################################### 
# 
# 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_[Se(SImes)]
_database_code_depnum_ccdc_archive 'CCDC 1024814'
_audit_update_record             
;
2014-09-17 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21 H26 N2 Se'
_chemical_formula_moiety         'C21 H26 N2 Se'
_chemical_formula_weight         385.41
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
_space_group_IT_number           60
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,-Y,1/2+Z
4 1/2-X,1/2-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,-Z
7 -X,+Y,1/2-Z
8 1/2+X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   15.9194(19)
_cell_length_b                   7.4418(7)
_cell_length_c                   16.1915(19)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1918.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4776
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800.00
_exptl_absorpt_coefficient_mu    1.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_T_max  0.889

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            21695
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_theta_max         25.384
_diffrn_reflns_theta_min         2.516
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1762
_reflns_number_gt                1480
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0715
_refine_ls_wR_factor_gt          0.0688
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1762
_refine_ls_number_parameters     113
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0356P)²+0.8647P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.5 0.99672(3) 0.75 0.03178(12) Uani 1 4 d . . .
N2 N 0.46430(10) 0.64595(19) 0.69237(9) 0.0314(3) Uani 1 8 d . . .
C1 C 0.5 0.7510(3) 0.75 0.0257(5) Uani 1 4 d . . .
C3 C 0.48162(16) 0.4551(3) 0.70655(14) 0.0445(5) Uani 1 8 d . . .
C4 C 0.42243(11) 0.7087(2) 0.61935(10) 0.0277(4) Uani 1 8 d . . .
C5 C 0.33545(12) 0.7274(3) 0.62146(10) 0.0340(4) Uani 1 8 d . . .
C6 C 0.29487(12) 0.7856(3) 0.55063(12) 0.0380(5) Uani 1 8 d . . .
C7 C 0.33899(12) 0.8258(3) 0.47891(11) 0.0336(4) Uani 1 8 d . . .
C8 C 0.42563(12) 0.8064(2) 0.47922(11) 0.0296(4) Uani 1 8 d . . .
C9 C 0.46871(11) 0.7455(2) 0.54843(10) 0.0276(4) Uani 1 8 d . . .
C10 C 0.28648(14) 0.6906(4) 0.69945(13) 0.0514(6) Uani 1 8 d . . .
C11 C 0.29358(14) 0.8904(3) 0.40283(13) 0.0486(6) Uani 1 8 d . . .
C12 C 0.56264(12) 0.7210(3) 0.54588(13) 0.0383(4) Uani 1 8 d . . .
H3A H 0.52246 0.40801 0.66584 0.0534 Uiso 1 8 calc R . .
H3B H 0.42951 0.38277 0.70385 0.0534 Uiso 1 8 calc R . .
H6 H 0.2355 0.79833 0.55111 0.0456 Uiso 1 8 calc R . .
H8 H 0.4564 0.83561 0.43077 0.0356 Uiso 1 8 calc R . .
H10A H 0.29923 0.78337 0.74054 0.0617 Uiso 1 8 calc R . .
H10B H 0.3022 0.57252 0.72133 0.0617 Uiso 1 8 calc R . .
H10C H 0.22621 0.69204 0.68712 0.0617 Uiso 1 8 calc R . .
H11A H 0.26293 0.79005 0.37781 0.0583 Uiso 1 8 calc R . .
H11B H 0.33439 0.93787 0.3631 0.0583 Uiso 1 8 calc R . .
H11C H 0.25388 0.98545 0.4181 0.0583 Uiso 1 8 calc R . .
H12A H 0.58566 0.78576 0.49828 0.0460 Uiso 1 8 calc R . .
H12B H 0.57589 0.59289 0.54093 0.0460 Uiso 1 8 calc R . .
H12C H 0.58745 0.76857 0.59678 0.0460 Uiso 1 8 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Se1 C1 1.829(2) yes . .
N2 C1 1.343(2) yes . .
N2 C3 1.465(3) yes . .
N2 C4 1.435(2) yes . .
C3 C3 1.524(3) yes . 7_656
C4 C5 1.392(3) yes . .
C4 C9 1.391(2) yes . .
C5 C6 1.386(3) yes . .
C5 C10 1.509(3) yes . .
C6 C7 1.390(3) yes . .
C7 C8 1.387(3) yes . .
C7 C11 1.507(3) yes . .
C8 C9 1.390(2) yes . .
C9 C12 1.507(3) yes . .
C3 H3A 0.990 no . .
C3 H3B 0.990 no . .
C6 H6 0.950 no . .
C8 H8 0.950 no . .
C10 H10A 0.980 no . .
C10 H10B 0.980 no . .
C10 H10C 0.980 no . .
C11 H11A 0.980 no . .
C11 H11B 0.980 no . .
C11 H11C 0.980 no . .
C12 H12A 0.980 no . .
C12 H12B 0.980 no . .
C12 H12C 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N2 C3 112.07(16) yes . . .
C1 N2 C4 125.38(15) yes . . .
C3 N2 C4 122.15(15) yes . . .
Se1 C1 N2 125.58(10) yes . . .
Se1 C1 N2 125.58(10) yes . . 7_656
N2 C1 N2 108.83(18) yes . . 7_656
N2 C3 C3 102.53(17) yes . . 7_656
N2 C4 C5 118.30(15) yes . . .
N2 C4 C9 119.86(16) yes . . .
C5 C4 C9 121.83(15) yes . . .
C4 C5 C6 118.33(16) yes . . .
C4 C5 C10 121.09(16) yes . . .
C6 C5 C10 120.56(18) yes . . .
C5 C6 C7 121.55(18) yes . . .
C6 C7 C8 118.51(17) yes . . .
C6 C7 C11 120.62(18) yes . . .
C8 C7 C11 120.88(17) yes . . .
C7 C8 C9 121.84(17) yes . . .
C4 C9 C8 117.92(16) yes . . .
C4 C9 C12 121.62(16) yes . . .
C8 C9 C12 120.46(16) yes . . .
N2 C3 H3A 111.260 no . . .
N2 C3 H3B 111.263 no . . .
C3 C3 H3A 111.258 no 7_656 . .
C3 C3 H3B 111.259 no 7_656 . .
H3A C3 H3B 109.167 no . . .
C5 C6 H6 119.226 no . . .
C7 C6 H6 119.224 no . . .
C7 C8 H8 119.081 no . . .
C9 C8 H8 119.075 no . . .
C5 C10 H10A 109.468 no . . .
C5 C10 H10B 109.468 no . . .
C5 C10 H10C 109.469 no . . .
H10A C10 H10B 109.473 no . . .
H10A C10 H10C 109.471 no . . .
H10B C10 H10C 109.478 no . . .
C7 C11 H11A 109.469 no . . .
C7 C11 H11B 109.480 no . . .
C7 C11 H11C 109.476 no . . .
H11A C11 H11B 109.466 no . . .
H11A C11 H11C 109.463 no . . .
H11B C11 H11C 109.473 no . . .
C9 C12 H12A 109.469 no . . .
C9 C12 H12B 109.471 no . . .
C9 C12 H12C 109.470 no . . .
H12A C12 H12B 109.480 no . . .
H12A C12 H12C 109.470 no . . .
H12B C12 H12C 109.468 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N2 C3 C3 11.88(19) no . . . 7_656
C3 N2 C1 Se1 175.10(11) no . . . .
C3 N2 C1 N2 -4.90(15) no . . . 7_656
C1 N2 C4 C5 -95.69(18) no . . . .
C1 N2 C4 C9 85.67(19) no . . . .
C4 N2 C1 Se1 2.24(19) no . . . .
C4 N2 C1 N2 -177.76(13) no . . . 7_656
C3 N2 C4 C5 92.1(2) no . . . .
C3 N2 C4 C9 -86.5(2) no . . . .
C4 N2 C3 C3 -175.00(14) no . . . 7_656
N2 C3 C3 N2 -13.4(2) no . . 7_656 7_656
N2 C4 C5 C6 -179.11(13) no . . . .
N2 C4 C5 C10 2.7(2) no . . . .
N2 C4 C9 C8 -179.85(13) no . . . .
N2 C4 C9 C12 0.0(2) no . . . .
C5 C4 C9 C8 1.6(2) no . . . .
C5 C4 C9 C12 -178.58(15) no . . . .
C9 C4 C5 C6 -0.5(3) no . . . .
C9 C4 C5 C10 -178.73(14) no . . . .
C4 C5 C6 C7 -0.3(3) no . . . .
C10 C5 C6 C7 177.91(17) no . . . .
C5 C6 C7 C8 0.0(3) no . . . .
C5 C6 C7 C11 -179.46(16) no . . . .
C6 C7 C8 C9 1.1(3) no . . . .
C11 C7 C8 C9 -179.41(16) no . . . .
C7 C8 C9 C4 -1.9(3) no . . . .
C7 C8 C9 C12 178.27(15) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Se1 C4 3.2546(17) no . .
Se1 C4 3.2546(17) no . 7_656
N2 C4 3.573(2) no . 7_656
N2 C10 2.853(3) no . .
N2 C12 2.896(3) no . .
C1 C3 2.330(3) no . 7_656
C1 C4 2.4696(17) no . 7_656
C1 C5 3.3503(18) no . .
C1 C5 3.3503(18) no . 7_656
C1 C9 3.3018(17) no . .
C1 C9 3.3018(17) no . 7_656
C1 C10 3.525(2) no . .
C1 C10 3.525(2) no . 7_656
C1 C12 3.459(2) no . .
C1 C12 3.459(2) no . 7_656
C3 C5 3.379(3) no . .
C3 C9 3.357(3) no . .
C3 C10 3.569(3) no . .
C3 C12 3.514(3) no . .
C4 C7 2.774(2) no . .
C5 C8 2.777(3) no . .
C6 C9 2.784(3) no . .
Se1 C3 3.495(2) no . 1_565
Se1 C3 3.495(2) no . 7_666
C3 Se1 3.495(2) no . 1_545
C8 C12 3.545(3) no . 5_676
C10 C11 3.582(3) no . 4_565
C11 C10 3.582(3) no . 4_564
C12 C8 3.545(3) no . 5_676
Se1 H10A 3.5721 no . .
Se1 H10A 3.5721 no . 7_656
Se1 H12C 3.3129 no . .
Se1 H12C 3.3129 no . 7_656
N2 H3A 2.9070 no . 7_656
N2 H3B 3.0850 no . 7_656
N2 H10A 2.9257 no . .
N2 H10B 2.6791 no . .
N2 H12B 3.0536 no . .
N2 H12C 2.6593 no . .
C1 H3A 2.9154 no . .
C1 H3A 2.9154 no . 7_656
C1 H3B 3.0540 no . .
C1 H3B 3.0540 no . 7_656
C1 H10A 3.2089 no . .
C1 H10A 3.2089 no . 7_656
C1 H10B 3.4489 no . .
C1 H10B 3.4489 no . 7_656
C1 H12C 2.8478 no . .
C1 H12C 2.8478 no . 7_656
C3 H10B 2.9965 no . .
C3 H12B 3.2395 no . .
C3 H12C 3.3821 no . .
C4 H3A 2.8480 no . .
C4 H3B 2.7874 no . .
C4 H6 3.2436 no . .
C4 H8 3.2414 no . .
C4 H10A 2.8294 no . .
C4 H10B 2.7235 no . .
C4 H10C 3.3132 no . .
C4 H12A 3.3051 no . .
C4 H12B 2.8851 no . .
C4 H12C 2.6894 no . .
C5 H3B 3.2556 no . .
C6 H8 3.2430 no . .
C6 H10A 3.0758 no . .
C6 H10B 3.1886 no . .
C6 H10C 2.5619 no . .
C6 H11A 2.8442 no . .
C6 H11B 3.3014 no . .
C6 H11C 2.6912 no . .
C8 H6 3.2434 no . .
C8 H11A 3.0691 no . .
C8 H11B 2.5694 no . .
C8 H11C 3.1984 no . .
C8 H12A 2.5708 no . .
C8 H12B 3.0406 no . .
C8 H12C 3.2154 no . .
C9 H3A 3.2640 no . .
C10 H3B 3.2307 no . .
C10 H6 2.6590 no . .
C11 H6 2.6625 no . .
C11 H8 2.6626 no . .
C12 H3A 3.0997 no . .
C12 H8 2.6573 no . .
H3A H3A 2.8176 no . 7_656
H3A H3B 2.2520 no . 7_656
H3A H10B 3.5535 no . 7_656
H3A H12B 2.5898 no . .
H3A H12C 3.0855 no . .
H3B H3B 2.6964 no . 7_656
H3B H10B 2.4863 no . .
H6 H10A 3.2325 no . .
H6 H10B 3.3982 no . .
H6 H10C 2.3446 no . .
H6 H11A 2.8404 no . .
H6 H11B 3.5810 no . .
H6 H11C 2.5812 no . .
H8 H11A 3.2150 no . .
H8 H11B 2.3563 no . .
H8 H11C 3.4175 no . .
H8 H12A 2.3594 no . .
H8 H12B 3.1721 no . .
H8 H12C 3.4389 no . .
H10A H12C 3.1945 no . 7_656
Se1 H3A 3.3694 no . 1_565
Se1 H3A 3.3694 no . 7_666
Se1 H3B 3.1735 no . 1_565
Se1 H3B 3.1735 no . 7_666
Se1 H8 3.2566 no . 3_575
Se1 H8 3.2566 no . 5_676
Se1 H11B 3.2467 no . 3_575
Se1 H11B 3.2467 no . 5_676
C3 H8 3.2555 no . 5_666
C4 H12B 3.4314 no . 5_666
C5 H6 3.5733 no . 2_545
C6 H11C 3.1932 no . 2_545
C6 H12A 3.4643 no . 6_466
C7 H11C 3.0936 no . 2_545
C7 H12A 3.1514 no . 5_676
C7 H12B 3.4129 no . 5_666
C7 H12C 3.4620 no . 5_676
C8 H3A 2.9573 no . 5_666
C8 H8 3.5704 no . 5_676
C8 H12A 3.0620 no . 5_676
C8 H12B 2.9895 no . 5_666
C8 H12C 3.4002 no . 5_676
C9 H8 3.3545 no . 5_676
C9 H12B 2.9898 no . 5_666
C10 H10A 3.3895 no . 2_545
C10 H10B 3.1932 no . 2_555
C10 H11A 2.9966 no . 4_565
C10 H11B 3.4114 no . 4_565
C11 H10A 3.5784 no . 3_574
C11 H10A 3.2804 no . 4_564
C11 H10B 3.3222 no . 4_564
C11 H10C 3.5602 no . 4_564
C11 H11A 3.1331 no . 2_555
C11 H11C 3.1170 no . 2_545
C11 H12A 3.4736 no . 5_676
C11 H12B 3.5853 no . 6_466
C11 H12C 3.1664 no . 5_676
C11 H12C 3.4883 no . 6_466
C12 H6 3.1717 no . 6_566
C12 H8 3.3347 no . 5_676
C12 H11A 3.4205 no . 6_566
C12 H11B 3.3619 no . 5_676
C12 H11C 3.4598 no . 6_566
C12 H12B 3.5067 no . 5_666
H3A Se1 3.3694 no . 1_545
H3A C8 2.9573 no . 5_666
H3A H8 2.4181 no . 5_666
H3A H11B 3.4696 no . 5_666
H3A H12A 3.4790 no . 5_666
H3B Se1 3.1735 no . 1_545
H3B H8 3.2697 no . 5_666
H3B H10C 2.8694 no . 2_545
H3B H12A 3.5132 no . 5_666
H6 C5 3.5733 no . 2_555
H6 C12 3.1717 no . 6_466
H6 H10B 3.4814 no . 2_555
H6 H11C 3.1762 no . 2_545
H6 H12A 2.5925 no . 6_466
H6 H12B 3.0549 no . 6_466
H6 H12C 3.3966 no . 6_466
H8 Se1 3.2566 no . 3_574
H8 C3 3.2555 no . 5_666
H8 C8 3.5704 no . 5_676
H8 C9 3.3545 no . 5_676
H8 C12 3.3347 no . 5_676
H8 H3A 2.4181 no . 5_666
H8 H3B 3.2697 no . 5_666
H8 H8 3.5971 no . 5_676
H8 H12A 3.1157 no . 5_676
H8 H12B 3.2623 no . 5_666
H8 H12C 3.0599 no . 5_676
H10A C10 3.3895 no . 2_555
H10A C11 3.5784 no . 3_575
H10A C11 3.2804 no . 4_565
H10A H10B 2.7082 no . 2_555
H10A H10C 3.1877 no . 2_555
H10A H11A 2.4935 no . 4_565
H10A H11B 2.9248 no . 3_575
H10A H11B 3.3427 no . 4_565
H10A H11C 3.4273 no . 3_575
H10B C10 3.1932 no . 2_545
H10B C11 3.3222 no . 4_565
H10B H6 3.4814 no . 2_545
H10B H10A 2.7082 no . 2_545
H10B H10C 2.9204 no . 2_545
H10B H11A 2.9224 no . 4_565
H10B H11B 3.1628 no . 4_565
H10B H11C 3.3367 no . 4_565
H10C C11 3.5602 no . 4_565
H10C H3B 2.8694 no . 2_555
H10C H10A 3.1877 no . 2_545
H10C H10B 2.9204 no . 2_555
H10C H11A 3.0953 no . 4_565
H10C H11B 3.1598 no . 4_565
H11A C10 2.9966 no . 4_564
H11A C11 3.1331 no . 2_545
H11A C12 3.4205 no . 6_466
H11A H10A 2.4935 no . 4_564
H11A H10B 2.9224 no . 4_564
H11A H10C 3.0953 no . 4_564
H11A H11B 3.0538 no . 2_545
H11A H11C 2.3739 no . 2_545
H11A H12A 3.5082 no . 6_466
H11A H12B 3.3699 no . 6_466
H11A H12C 2.8572 no . 6_466
H11B Se1 3.2467 no . 3_574
H11B C10 3.4114 no . 4_564
H11B C12 3.3619 no . 5_676
H11B H3A 3.4696 no . 5_666
H11B H10A 2.9248 no . 3_574
H11B H10A 3.3427 no . 4_564
H11B H10B 3.1628 no . 4_564
H11B H10C 3.1598 no . 4_564
H11B H11A 3.0538 no . 2_555
H11B H12A 3.2996 no . 5_676
H11B H12C 2.5967 no . 5_676
H11C C6 3.1932 no . 2_555
H11C C7 3.0936 no . 2_555
H11C C11 3.1170 no . 2_555
H11C C12 3.4598 no . 6_466
H11C H6 3.1762 no . 2_555
H11C H10A 3.4273 no . 3_574
H11C H10B 3.3367 no . 4_564
H11C H11A 2.3739 no . 2_555
H11C H12A 3.3552 no . 5_676
H11C H12B 2.9679 no . 6_466
H11C H12C 3.1288 no . 5_676
H11C H12C 3.2636 no . 6_466
H12A C6 3.4643 no . 6_566
H12A C7 3.1514 no . 5_676
H12A C8 3.0620 no . 5_676
H12A C11 3.4736 no . 5_676
H12A H3A 3.4790 no . 5_666
H12A H3B 3.5132 no . 5_666
H12A H6 2.5925 no . 6_566
H12A H8 3.1157 no . 5_676
H12A H11A 3.5082 no . 6_566
H12A H11B 3.2996 no . 5_676
H12A H11C 3.3552 no . 5_676
H12B C4 3.4314 no . 5_666
H12B C7 3.4129 no . 5_666
H12B C8 2.9895 no . 5_666
H12B C9 2.9898 no . 5_666
H12B C11 3.5853 no . 6_566
H12B C12 3.5067 no . 5_666
H12B H6 3.0549 no . 6_566
H12B H8 3.2623 no . 5_666
H12B H11A 3.3699 no . 6_566
H12B H11C 2.9679 no . 6_566
H12B H12B 3.0833 no . 5_666
H12C C7 3.4620 no . 5_676
H12C C8 3.4002 no . 5_676
H12C C11 3.1664 no . 5_676
H12C C11 3.4883 no . 6_566
H12C H6 3.3966 no . 6_566
H12C H8 3.0599 no . 5_676
H12C H11A 2.8572 no . 6_566
H12C H11B 2.5967 no . 5_676
H12C H11C 3.1288 no . 5_676
H12C H11C 3.2636 no . 6_566

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_chemical_name_systematic        '[Se(SIMes)]'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform, pentane'
####################################################################### 
# 
# 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_[Se(Tr2)]
_database_code_depnum_ccdc_archive 'CCDC 1024815'
_audit_update_record             
;
2014-09-17 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C11 H6 F5 N3 Se'
_chemical_formula_moiety         'C11 H6 F5 N3 Se'
_chemical_formula_weight         354.14
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.3746(16)
_cell_length_b                   15.527(3)
_cell_length_c                   8.3524(14)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.357(5)
_cell_angle_gamma                90.0000
_cell_volume                     1215.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2746
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688.00
_exptl_absorpt_coefficient_mu    3.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_T_max  0.910

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            14536
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_theta_max         25.407
_diffrn_reflns_theta_min         2.173
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2221
_reflns_number_gt                1606
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1104
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2221
_refine_ls_number_parameters     181
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0749P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.30
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.03999(5) 0.17604(3) 0.25566(5) 0.0497(2) Uani 1 4 d . . .
F1 F 0.3960(3) -0.00427(16) 0.2066(4) 0.0579(7) Uani 1 4 d . . .
F2 F 0.6213(3) 0.02939(17) 0.4040(3) 0.0576(7) Uani 1 4 d . . .
F3 F 0.7136(3) 0.19326(18) 0.4387(3) 0.0561(7) Uani 1 4 d . . .
F4 F 0.5887(3) 0.32245(16) 0.2748(3) 0.0597(7) Uani 1 4 d . . .
F5 F 0.3622(3) 0.28946(16) 0.0793(3) 0.0508(6) Uani 1 4 d . . .
N2 N 0.2583(4) 0.1242(2) 0.0367(4) 0.0398(8) Uani 1 4 d . . .
N3 N 0.2825(4) 0.0925(2) -0.1173(4) 0.0451(9) Uani 1 4 d . . .
N5 N 0.0544(4) 0.1122(2) -0.0661(4) 0.0364(8) Uani 1 4 d . . .
C1 C 0.1194(5) 0.1363(3) 0.0708(5) 0.0380(9) Uani 1 4 d . . .
C4 C 0.1539(5) 0.0874(3) -0.1739(5) 0.0405(10) Uani 1 4 d . . .
C6 C 0.3758(4) 0.1416(3) 0.1388(5) 0.0386(9) Uani 1 4 d . . .
C7 C 0.4438(5) 0.0758(3) 0.2224(5) 0.0421(10) Uani 1 4 d . . .
C8 C 0.5578(5) 0.0926(3) 0.3227(5) 0.0437(10) Uani 1 4 d . . .
C9 C 0.6059(5) 0.1756(3) 0.3369(5) 0.0427(10) Uani 1 4 d . . .
C10 C 0.5406(5) 0.2420(3) 0.2566(5) 0.0436(10) Uani 1 4 d . . .
C11 C 0.4254(5) 0.2250(3) 0.1574(5) 0.0406(10) Uani 1 4 d . . .
C12 C 0.0843(5) 0.0602(3) -0.3273(5) 0.0496(11) Uani 1 4 d . . .
C13 C -0.0707(5) 0.0881(3) -0.3031(6) 0.0549(13) Uani 1 4 d . . .
C14 C -0.0925(4) 0.1077(3) -0.1245(5) 0.0437(10) Uani 1 4 d . . .
H12A H 0.09143 -0.00284 -0.34297 0.0595 Uiso 1 4 calc R . .
H12B H 0.12718 0.08988 -0.42023 0.0595 Uiso 1 4 calc R . .
H13A H -0.13613 0.04159 -0.33785 0.0659 Uiso 1 4 calc R . .
H13B H -0.09142 0.14007 -0.36787 0.0659 Uiso 1 4 calc R . .
H14A H -0.14299 0.16298 -0.10896 0.0525 Uiso 1 4 calc R . .
H14B H -0.14618 0.06104 -0.07096 0.0525 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Se1 C1 1.826(4) yes . .
F1 C7 1.328(5) yes . .
F2 C8 1.332(5) yes . .
F3 C9 1.344(5) yes . .
F4 C10 1.336(5) yes . .
F5 C11 1.332(5) yes . .
N2 N3 1.397(5) yes . .
N2 C1 1.348(5) yes . .
N2 C6 1.415(5) yes . .
N3 C4 1.295(6) yes . .
N5 C1 1.346(5) yes . .
N5 C4 1.356(5) yes . .
N5 C14 1.459(5) yes . .
C4 C12 1.496(6) yes . .
C6 C7 1.390(6) yes . .
C6 C11 1.385(6) yes . .
C7 C8 1.379(6) yes . .
C8 C9 1.370(6) yes . .
C9 C10 1.372(6) yes . .
C10 C11 1.383(6) yes . .
C12 C13 1.530(7) yes . .
C13 C14 1.537(6) yes . .
C12 H12A 0.990 no . .
C12 H12B 0.990 no . .
C13 H13A 0.990 no . .
C13 H13B 0.990 no . .
C14 H14A 0.990 no . .
C14 H14B 0.990 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N3 N2 C1 114.0(3) yes . . .
N3 N2 C6 119.5(3) yes . . .
C1 N2 C6 126.6(3) yes . . .
N2 N3 C4 101.6(3) yes . . .
C1 N5 C4 109.5(3) yes . . .
C1 N5 C14 135.9(3) yes . . .
C4 N5 C14 114.6(3) yes . . .
Se1 C1 N2 128.7(3) yes . . .
Se1 C1 N5 128.9(3) yes . . .
N2 C1 N5 102.4(3) yes . . .
N3 C4 N5 112.6(4) yes . . .
N3 C4 C12 136.9(4) yes . . .
N5 C4 C12 110.5(4) yes . . .
N2 C6 C7 121.1(4) yes . . .
N2 C6 C11 120.3(4) yes . . .
C7 C6 C11 118.6(4) yes . . .
F1 C7 C6 119.0(4) yes . . .
F1 C7 C8 119.9(4) yes . . .
C6 C7 C8 121.2(4) yes . . .
F2 C8 C7 120.8(4) yes . . .
F2 C8 C9 120.2(4) yes . . .
C7 C8 C9 119.0(4) yes . . .
F3 C9 C8 119.5(4) yes . . .
F3 C9 C10 119.2(4) yes . . .
C8 C9 C10 121.3(4) yes . . .
F4 C10 C9 119.9(4) yes . . .
F4 C10 C11 120.5(4) yes . . .
C9 C10 C11 119.6(4) yes . . .
F5 C11 C6 120.0(4) yes . . .
F5 C11 C10 119.6(4) yes . . .
C6 C11 C10 120.4(4) yes . . .
C4 C12 C13 102.5(4) yes . . .
C12 C13 C14 108.4(4) yes . . .
N5 C14 C13 101.7(3) yes . . .
C4 C12 H12A 111.271 no . . .
C4 C12 H12B 111.270 no . . .
C13 C12 H12A 111.266 no . . .
C13 C12 H12B 111.262 no . . .
H12A C12 H12B 109.172 no . . .
C12 C13 H13A 110.006 no . . .
C12 C13 H13B 110.007 no . . .
C14 C13 H13A 110.012 no . . .
C14 C13 H13B 110.009 no . . .
H13A C13 H13B 108.364 no . . .
N5 C14 H14A 111.440 no . . .
N5 C14 H14B 111.433 no . . .
C13 C14 H14A 111.435 no . . .
C13 C14 H14B 111.426 no . . .
H14A C14 H14B 109.274 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N3 N2 C1 Se1 179.8(3) no . . . .
N3 N2 C1 N5 -0.5(4) no . . . .
C1 N2 N3 C4 0.9(4) no . . . .
N3 N2 C6 C7 -80.2(5) no . . . .
N3 N2 C6 C11 99.9(4) no . . . .
C6 N2 N3 C4 -178.2(3) no . . . .
C1 N2 C6 C7 100.8(5) no . . . .
C1 N2 C6 C11 -79.1(5) no . . . .
C6 N2 C1 Se1 -1.2(6) no . . . .
C6 N2 C1 N5 178.5(3) no . . . .
N2 N3 C4 N5 -0.9(4) no . . . .
N2 N3 C4 C12 -179.9(4) no . . . .
C1 N5 C4 N3 0.7(4) no . . . .
C1 N5 C4 C12 180.0(3) no . . . .
C4 N5 C1 Se1 179.6(3) no . . . .
C4 N5 C1 N2 -0.1(4) no . . . .
C1 N5 C14 C13 170.5(4) no . . . .
C14 N5 C1 Se1 0.6(7) no . . . .
C14 N5 C1 N2 -179.1(4) no . . . .
C4 N5 C14 C13 -8.4(4) no . . . .
C14 N5 C4 N3 179.9(3) no . . . .
C14 N5 C4 C12 -0.8(4) no . . . .
N3 C4 C12 C13 -171.3(4) no . . . .
N5 C4 C12 C13 9.7(4) no . . . .
N2 C6 C7 F1 -0.7(6) no . . . .
N2 C6 C7 C8 -179.6(3) no . . . .
N2 C6 C11 F5 0.1(6) no . . . .
N2 C6 C11 C10 -179.7(3) no . . . .
C7 C6 C11 F5 -179.8(3) no . . . .
C7 C6 C11 C10 0.3(6) no . . . .
C11 C6 C7 F1 179.3(3) no . . . .
C11 C6 C7 C8 0.3(6) no . . . .
F1 C7 C8 F2 0.2(6) no . . . .
F1 C7 C8 C9 179.7(3) no . . . .
C6 C7 C8 F2 179.1(4) no . . . .
C6 C7 C8 C9 -1.3(6) no . . . .
F2 C8 C9 F3 -2.9(6) no . . . .
F2 C8 C9 C10 -178.8(3) no . . . .
C7 C8 C9 F3 177.6(4) no . . . .
C7 C8 C9 C10 1.7(6) no . . . .
F3 C9 C10 F4 3.1(6) no . . . .
F3 C9 C10 C11 -176.9(3) no . . . .
C8 C9 C10 F4 179.0(4) no . . . .
C8 C9 C10 C11 -1.0(6) no . . . .
F4 C10 C11 F5 0.1(6) no . . . .
F4 C10 C11 C6 180.0(3) no . . . .
C9 C10 C11 F5 -179.9(3) no . . . .
C9 C10 C11 C6 0.0(6) no . . . .
C4 C12 C13 C14 -14.7(5) no . . . .
C12 C13 C14 N5 14.2(5) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Se1 C6 3.345(4) no . .
Se1 C14 3.564(4) no . .
F1 F2 2.722(4) no . .
F1 N2 2.763(4) no . .
F1 N3 3.267(4) no . .
F1 C1 3.569(5) no . .
F1 C9 3.583(5) no . .
F1 C11 3.594(5) no . .
F2 F3 2.702(4) no . .
F3 F4 2.692(4) no . .
F3 C7 3.595(5) no . .
F4 F5 2.719(4) no . .
F5 N2 2.766(4) no . .
F5 N3 3.549(4) no . .
F5 C1 3.292(5) no . .
F5 C9 3.594(5) no . .
N2 C12 3.582(6) no . .
N2 C14 3.555(5) no . .
N3 C7 3.217(5) no . .
N3 C11 3.355(5) no . .
N3 C14 3.523(5) no . .
N5 C6 3.486(5) no . .
C1 C7 3.419(6) no . .
C1 C11 3.260(6) no . .
C1 C12 3.542(6) no . .
C4 C6 3.433(6) no . .
C6 C9 2.762(6) no . .
C7 C10 2.750(6) no . .
C8 C11 2.766(6) no . .
Se1 F3 3.440(3) no . 1_455
F1 F2 3.281(4) no . 3_656
F1 F4 2.699(4) no . 2_645
F1 N3 3.398(4) no . 3_655
F1 C13 3.417(6) no . 3_555
F1 C14 3.334(5) no . 3_555
F2 F1 3.281(4) no . 3_656
F2 F2 2.936(4) no . 3_656
F2 N3 3.187(4) no . 3_655
F2 C4 3.388(5) no . 3_655
F2 C7 3.578(5) no . 3_656
F2 C8 3.416(5) no . 3_656
F2 C12 3.160(5) no . 3_655
F3 Se1 3.440(3) no . 1_655
F3 F4 3.058(4) no . 4_555
F3 F5 3.514(4) no . 4_555
F3 C10 3.278(5) no . 4_555
F3 C11 3.508(5) no . 4_555
F3 C13 3.370(6) no . 1_656
F4 F1 2.699(4) no . 2_655
F4 F3 3.058(4) no . 4_554
F4 N3 3.290(5) no . 4_555
F4 C13 3.546(6) no . 4_655
F4 C14 3.284(5) no . 4_655
F5 F3 3.514(4) no . 4_554
F5 N3 3.219(4) no . 4_555
F5 C4 3.431(5) no . 4_555
F5 C8 3.370(5) no . 4_554
F5 C9 3.110(5) no . 4_554
F5 C10 3.218(5) no . 4_554
F5 C11 3.583(5) no . 4_554
F5 C12 3.588(5) no . 4_555
N3 F1 3.398(4) no . 3_655
N3 F2 3.187(4) no . 3_655
N3 F4 3.290(5) no . 4_554
N3 F5 3.219(4) no . 4_554
C4 F2 3.388(5) no . 3_655
C4 F5 3.431(5) no . 4_554
C7 F2 3.578(5) no . 3_656
C8 F2 3.416(5) no . 3_656
C8 F5 3.370(5) no . 4_555
C9 F5 3.110(5) no . 4_555
C9 C11 3.531(6) no . 4_555
C10 F3 3.278(5) no . 4_554
C10 F5 3.218(5) no . 4_555
C10 C11 3.561(6) no . 4_555
C11 F3 3.508(5) no . 4_554
C11 F5 3.583(5) no . 4_555
C11 C9 3.531(6) no . 4_554
C11 C10 3.561(6) no . 4_554
C12 F2 3.160(5) no . 3_655
C12 F5 3.588(5) no . 4_554
C13 F1 3.417(6) no . 3_555
C13 F3 3.370(6) no . 1_454
C13 F4 3.546(6) no . 4_454
C14 F1 3.334(5) no . 3_555
C14 F4 3.284(5) no . 4_454
Se1 H14A 3.4919 no . .
N3 H12A 2.9850 no . .
N3 H12B 2.9116 no . .
N5 H12A 2.9437 no . .
N5 H12B 3.0590 no . .
N5 H13A 3.0806 no . .
N5 H13B 2.8921 no . .
C1 H14A 2.9030 no . .
C1 H14B 2.9879 no . .
C4 H13A 3.1191 no . .
C4 H13B 2.9218 no . .
C4 H14A 3.0716 no . .
C4 H14B 2.9749 no . .
C12 H14A 3.2341 no . .
C12 H14B 3.0511 no . .
C14 H12A 3.0469 no . .
C14 H12B 3.2373 no . .
H12A H13A 2.2427 no . .
H12A H13B 2.8108 no . .
H12A H14B 3.3422 no . .
H12B H13A 2.6739 no . .
H12B H13B 2.2381 no . .
H13A H14A 2.6857 no . .
H13A H14B 2.2521 no . .
H13B H14A 2.2472 no . .
H13B H14B 2.8169 no . .
Se1 H12A 3.0484 no . 3_555
Se1 H12B 3.1239 no . 1_556
Se1 H13A 3.5629 no . 3_555
Se1 H13B 3.4301 no . 1_556
Se1 H13B 3.2739 no . 4_555
Se1 H14A 3.2392 no . 4_555
F1 H13A 2.7395 no . 3_555
F1 H14A 3.5125 no . 3_555
F1 H14B 2.7405 no . 3_555
F2 H12A 2.7748 no . 3_655
F2 H12B 3.0006 no . 3_655
F2 H13A 3.1297 no . 1_656
F3 H12A 3.5695 no . 3_655
F3 H13A 3.3139 no . 1_656
F3 H13B 2.5686 no . 1_656
F3 H14A 2.6374 no . 4_655
F4 H13A 3.4679 no . 4_655
F4 H13B 3.2856 no . 4_655
F4 H14A 2.7002 no . 4_655
F4 H14B 3.3273 no . 4_655
F5 H12B 2.8920 no . 4_555
N2 H14B 3.0767 no . 3_555
N3 H14B 3.1328 no . 3_555
N5 H14B 3.0449 no . 3_555
C1 H13A 3.5535 no . 3_555
C1 H14B 3.0746 no . 3_555
C4 H14B 3.0826 no . 3_555
C7 H13A 3.5507 no . 3_555
C8 H12A 3.5743 no . 3_655
C9 H14A 3.4655 no . 4_655
C10 H14A 3.4917 no . 4_655
C12 H12A 3.3215 no . 3_554
C12 H13A 3.2515 no . 3_554
C13 H12A 3.2436 no . 3_554
H12A Se1 3.0484 no . 3_555
H12A F2 2.7748 no . 3_655
H12A F3 3.5695 no . 3_655
H12A C8 3.5743 no . 3_655
H12A C12 3.3215 no . 3_554
H12A C13 3.2436 no . 3_554
H12A H12A 3.1259 no . 3_554
H12A H12B 3.1445 no . 3_554
H12A H13A 2.7674 no . 3_554
H12A H13B 3.2207 no . 3_554
H12B Se1 3.1239 no . 1_554
H12B F2 3.0006 no . 3_655
H12B F5 2.8920 no . 4_554
H12B H12A 3.1445 no . 3_554
H12B H13A 2.8738 no . 3_554
H13A Se1 3.5629 no . 3_555
H13A F1 2.7395 no . 3_555
H13A F2 3.1297 no . 1_454
H13A F3 3.3139 no . 1_454
H13A F4 3.4679 no . 4_454
H13A C1 3.5535 no . 3_555
H13A C7 3.5507 no . 3_555
H13A C12 3.2515 no . 3_554
H13A H12A 2.7674 no . 3_554
H13A H12B 2.8738 no . 3_554
H13B Se1 3.4301 no . 1_554
H13B Se1 3.2739 no . 4_554
H13B F3 2.5686 no . 1_454
H13B F4 3.2856 no . 4_454
H13B H12A 3.2207 no . 3_554
H14A Se1 3.2392 no . 4_554
H14A F1 3.5125 no . 3_555
H14A F3 2.6374 no . 4_454
H14A F4 2.7002 no . 4_454
H14A C9 3.4655 no . 4_454
H14A C10 3.4917 no . 4_454
H14B F1 2.7405 no . 3_555
H14B F4 3.3273 no . 4_454
H14B N2 3.0767 no . 3_555
H14B N3 3.1328 no . 3_555
H14B N5 3.0449 no . 3_555
H14B C1 3.0746 no . 3_555
H14B C4 3.0826 no . 3_555
H14B H14B 3.5312 no . 3_555

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_chemical_name_systematic        '[Se(Tr2)]'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone, hexane'
####################################################################### 
# 
# 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_[Se(Tr3)]
_database_code_depnum_ccdc_archive 'CCDC 1024816'
_audit_update_record             
;
2014-09-17 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C11 H11 N3 O Se'
_chemical_formula_moiety         'C11 H11 N3 O Se'
_chemical_formula_weight         280.19
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.8283(13)
_cell_length_b                   7.9731(14)
_cell_length_c                   18.447(3)
_cell_angle_alpha                97.930(6)
_cell_angle_beta                 94.637(5)
_cell_angle_gamma                90.042(5)
_cell_volume                     1136.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2598
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560.00
_exptl_absorpt_coefficient_mu    3.286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.536
_exptl_absorpt_correction_T_max  0.936

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            13206
_diffrn_reflns_av_R_equivalents  0.1195
_diffrn_reflns_theta_max         25.519
_diffrn_reflns_theta_min         2.237
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4171
_reflns_number_gt                2576
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1583
_refine_ls_R_factor_gt           0.1235
_refine_ls_wR_factor_ref         0.3513
_refine_ls_wR_factor_gt          0.3333
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4171
_refine_ls_number_parameters     290
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         2.49
_refine_diff_density_min         -1.17
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.21448(19) 0.07797(18) 0.46052(8) 0.0410(5) Uani 1 2 d . . .
Se21 Se 0.10418(19) 0.20795(18) -0.02520(9) 0.0427(5) Uani 1 2 d . . .
O1 O 0.7952(13) 0.4420(15) 0.4352(6) 0.049(3) Uani 1 2 d . . .
O21 O 0.4276(14) 0.7920(14) -0.0687(6) 0.048(3) Uani 1 2 d . . .
N2 N 0.4416(14) 0.2462(14) 0.5807(6) 0.033(2) Uani 1 2 d . . .
N3 N 0.5997(14) 0.3333(14) 0.5947(7) 0.038(3) Uani 1 2 d . . .
N5 N 0.5311(15) 0.2635(14) 0.4767(7) 0.038(3) Uani 1 2 d . . .
N22 N 0.2451(15) 0.4688(14) 0.0887(7) 0.039(3) Uani 1 2 d . . .
N23 N 0.3191(14) 0.6274(15) 0.0981(7) 0.036(3) Uani 1 2 d . . .
N25 N 0.2697(15) 0.5298(15) -0.0182(7) 0.040(3) Uani 1 2 d . . .
C1 C 0.3948(15) 0.2026(14) 0.5100(8) 0.029(3) Uani 1 2 d . . .
C4 C 0.6446(19) 0.3421(17) 0.5303(8) 0.039(3) Uani 1 2 d . . .
C6 C 0.359(2) 0.2049(17) 0.6442(8) 0.040(3) Uani 1 2 d . . .
C7 C 0.183(2) 0.187(2) 0.6405(9) 0.051(4) Uani 1 2 d . . .
C8 C 0.107(2) 0.140(2) 0.7002(10) 0.054(4) Uani 1 2 d . . .
C9 C 0.209(3) 0.118(2) 0.7636(9) 0.065(5) Uani 1 2 d . . .
C10 C 0.383(3) 0.142(2) 0.7678(9) 0.060(5) Uani 1 2 d . . .
C11 C 0.461(3) 0.186(2) 0.7077(9) 0.057(4) Uani 1 2 d . . .
C12 C 0.8111(17) 0.4185(17) 0.5073(10) 0.044(4) Uani 1 2 d . . .
C13 C 0.733(2) 0.292(2) 0.3875(11) 0.055(4) Uani 1 2 d . . .
C14 C 0.547(2) 0.2534(18) 0.3978(8) 0.041(3) Uani 1 2 d . . .
C21 C 0.2121(19) 0.4101(18) 0.0162(8) 0.040(3) Uani 1 2 d . . .
C24 C 0.3325(18) 0.6620(18) 0.0316(8) 0.039(3) Uani 1 2 d . . .
C26 C 0.2086(18) 0.398(2) 0.1525(8) 0.041(3) Uani 1 2 d . . .
C27 C 0.238(2) 0.229(2) 0.1593(10) 0.055(4) Uani 1 2 d . . .
C28 C 0.198(2) 0.168(2) 0.2216(10) 0.057(5) Uani 1 2 d . . .
C29 C 0.126(2) 0.270(3) 0.2775(10) 0.062(5) Uani 1 2 d . . .
C30 C 0.097(2) 0.437(3) 0.2704(9) 0.059(5) Uani 1 2 d . . .
C31 C 0.140(2) 0.507(2) 0.2094(8) 0.045(4) Uani 1 2 d . . .
C32 C 0.395(2) 0.8216(19) 0.0075(9) 0.046(4) Uani 1 2 d . . .
C33 C 0.281(2) 0.714(2) -0.1099(8) 0.046(4) Uani 1 2 d . . .
C34 C 0.261(2) 0.533(2) -0.0987(8) 0.042(3) Uani 1 2 d . . .
H7 H 0.11454 0.20644 0.59752 0.0606 Uiso 1 2 calc R . .
H8 H -0.01388 0.12428 0.69798 0.0650 Uiso 1 2 calc R . .
H9 H 0.15688 0.08515 0.80441 0.0785 Uiso 1 2 calc R . .
H10 H 0.45024 0.12802 0.81173 0.0718 Uiso 1 2 calc R . .
H11 H 0.58149 0.20248 0.71013 0.0686 Uiso 1 2 calc R . .
H12A H 0.83736 0.52847 0.53827 0.0522 Uiso 1 2 calc R . .
H12B H 0.90777 0.34159 0.51562 0.0522 Uiso 1 2 calc R . .
H13A H 0.80447 0.19495 0.39782 0.0662 Uiso 1 2 calc R . .
H13B H 0.74294 0.30892 0.33583 0.0662 Uiso 1 2 calc R . .
H14A H 0.47087 0.33628 0.37671 0.0490 Uiso 1 2 calc R . .
H14B H 0.51488 0.13858 0.37278 0.0490 Uiso 1 2 calc R . .
H27 H 0.28433 0.15576 0.12089 0.0655 Uiso 1 2 calc R . .
H28 H 0.22125 0.05276 0.22666 0.0678 Uiso 1 2 calc R . .
H29 H 0.09685 0.22539 0.32006 0.0740 Uiso 1 2 calc R . .
H30 H 0.04589 0.50706 0.30847 0.0714 Uiso 1 2 calc R . .
H31 H 0.12456 0.62346 0.20626 0.0540 Uiso 1 2 calc R . .
H32A H 0.30738 0.91068 0.01501 0.0554 Uiso 1 2 calc R . .
H32B H 0.50121 0.86187 0.03756 0.0554 Uiso 1 2 calc R . .
H33A H 0.28991 0.71946 -0.16275 0.0547 Uiso 1 2 calc R . .
H33B H 0.17709 0.77681 -0.09519 0.0547 Uiso 1 2 calc R . .
H34A H 0.14948 0.48634 -0.12207 0.0508 Uiso 1 2 calc R . .
H34B H 0.35377 0.46423 -0.12059 0.0508 Uiso 1 2 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Se1 C1 1.831(12) yes . .
Se21 C21 1.857(14) yes . .
O1 C12 1.36(2) yes . .
O1 C13 1.44(2) yes . .
O21 C32 1.44(2) yes . .
O21 C33 1.422(18) yes . .
N2 N3 1.407(16) yes . .
N2 C1 1.324(18) yes . .
N2 C6 1.46(2) yes . .
N3 C4 1.28(2) yes . .
N5 C1 1.393(18) yes . .
N5 C4 1.359(18) yes . .
N5 C14 1.46(2) yes . .
N22 N23 1.374(16) yes . .
N22 C21 1.359(18) yes . .
N22 C26 1.42(2) yes . .
N23 C24 1.31(2) yes . .
N25 C21 1.31(2) yes . .
N25 C24 1.362(17) yes . .
N25 C34 1.484(19) yes . .
C4 C12 1.55(2) yes . .
C6 C7 1.38(2) yes . .
C6 C11 1.39(2) yes . .
C7 C8 1.39(3) yes . .
C8 C9 1.39(3) yes . .
C9 C10 1.37(3) yes . .
C10 C11 1.40(3) yes . .
C13 C14 1.52(2) yes . .
C24 C32 1.50(2) yes . .
C26 C27 1.39(2) yes . .
C26 C31 1.40(2) yes . .
C27 C28 1.36(3) yes . .
C28 C29 1.38(3) yes . .
C29 C30 1.37(3) yes . .
C30 C31 1.39(3) yes . .
C33 C34 1.49(2) yes . .
C7 H7 0.950 no . .
C8 H8 0.950 no . .
C9 H9 0.950 no . .
C10 H10 0.950 no . .
C11 H11 0.950 no . .
C12 H12A 0.990 no . .
C12 H12B 0.990 no . .
C13 H13A 0.990 no . .
C13 H13B 0.990 no . .
C14 H14A 0.990 no . .
C14 H14B 0.990 no . .
C27 H27 0.950 no . .
C28 H28 0.950 no . .
C29 H29 0.950 no . .
C30 H30 0.950 no . .
C31 H31 0.950 no . .
C32 H32A 0.990 no . .
C32 H32B 0.990 no . .
C33 H33A 0.990 no . .
C33 H33B 0.990 no . .
C34 H34A 0.990 no . .
C34 H34B 0.990 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C12 O1 C13 112.4(13) yes . . .
C32 O21 C33 108.9(12) yes . . .
N3 N2 C1 113.9(11) yes . . .
N3 N2 C6 117.0(11) yes . . .
C1 N2 C6 128.9(11) yes . . .
N2 N3 C4 102.9(11) yes . . .
C1 N5 C4 108.1(12) yes . . .
C1 N5 C14 126.6(11) yes . . .
C4 N5 C14 125.2(12) yes . . .
N23 N22 C21 110.8(12) yes . . .
N23 N22 C26 117.9(11) yes . . .
C21 N22 C26 131.2(12) yes . . .
N22 N23 C24 104.8(11) yes . . .
C21 N25 C24 109.9(12) yes . . .
C21 N25 C34 127.3(12) yes . . .
C24 N25 C34 122.7(13) yes . . .
Se1 C1 N2 133.0(11) yes . . .
Se1 C1 N5 124.4(10) yes . . .
N2 C1 N5 102.3(10) yes . . .
N3 C4 N5 112.7(13) yes . . .
N3 C4 C12 129.0(13) yes . . .
N5 C4 C12 118.2(13) yes . . .
N2 C6 C7 119.9(13) yes . . .
N2 C6 C11 118.7(14) yes . . .
C7 C6 C11 121.4(16) yes . . .
C6 C7 C8 119.2(15) yes . . .
C7 C8 C9 119.5(18) yes . . .
C8 C9 C10 120.9(18) yes . . .
C9 C10 C11 120.1(16) yes . . .
C6 C11 C10 118.8(17) yes . . .
O1 C12 C4 111.5(11) yes . . .
O1 C13 C14 111.8(13) yes . . .
N5 C14 C13 107.5(12) yes . . .
Se21 C21 N22 127.6(12) yes . . .
Se21 C21 N25 127.7(11) yes . . .
N22 C21 N25 104.8(12) yes . . .
N23 C24 N25 109.7(13) yes . . .
N23 C24 C32 129.0(13) yes . . .
N25 C24 C32 121.2(13) yes . . .
N22 C26 C27 122.2(14) yes . . .
N22 C26 C31 117.5(14) yes . . .
C27 C26 C31 120.3(16) yes . . .
C26 C27 C28 119.5(16) yes . . .
C27 C28 C29 121.3(17) yes . . .
C28 C29 C30 119.0(18) yes . . .
C29 C30 C31 121.9(17) yes . . .
C26 C31 C30 117.9(16) yes . . .
O21 C32 C24 110.3(12) yes . . .
O21 C33 C34 111.9(13) yes . . .
N25 C34 C33 107.0(11) yes . . .
C6 C7 H7 120.405 no . . .
C8 C7 H7 120.399 no . . .
C7 C8 H8 120.243 no . . .
C9 C8 H8 120.246 no . . .
C8 C9 H9 119.539 no . . .
C10 C9 H9 119.540 no . . .
C9 C10 H10 119.966 no . . .
C11 C10 H10 119.958 no . . .
C6 C11 H11 120.601 no . . .
C10 C11 H11 120.603 no . . .
O1 C12 H12A 109.330 no . . .
O1 C12 H12B 109.329 no . . .
C4 C12 H12A 109.328 no . . .
C4 C12 H12B 109.330 no . . .
H12A C12 H12B 107.980 no . . .
O1 C13 H13A 109.263 no . . .
O1 C13 H13B 109.261 no . . .
C14 C13 H13A 109.261 no . . .
C14 C13 H13B 109.263 no . . .
H13A C13 H13B 107.936 no . . .
N5 C14 H14A 110.208 no . . .
N5 C14 H14B 110.203 no . . .
C13 C14 H14A 110.202 no . . .
C13 C14 H14B 110.198 no . . .
H14A C14 H14B 108.489 no . . .
C26 C27 H27 120.228 no . . .
C28 C27 H27 120.225 no . . .
C27 C28 H28 119.334 no . . .
C29 C28 H28 119.336 no . . .
C28 C29 H29 120.520 no . . .
C30 C29 H29 120.519 no . . .
C29 C30 H30 119.034 no . . .
C31 C30 H30 119.053 no . . .
C26 C31 H31 121.073 no . . .
C30 C31 H31 121.071 no . . .
O21 C32 H32A 109.600 no . . .
O21 C32 H32B 109.604 no . . .
C24 C32 H32A 109.607 no . . .
C24 C32 H32B 109.604 no . . .
H32A C32 H32B 108.134 no . . .
O21 C33 H33A 109.241 no . . .
O21 C33 H33B 109.242 no . . .
C34 C33 H33A 109.238 no . . .
C34 C33 H33B 109.234 no . . .
H33A C33 H33B 107.923 no . . .
N25 C34 H34A 110.319 no . . .
N25 C34 H34B 110.323 no . . .
C33 C34 H34A 110.312 no . . .
C33 C34 H34B 110.312 no . . .
H34A C34 H34B 108.556 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C12 O1 C13 C14 68.9(15) no . . . .
C13 O1 C12 C4 -50.6(14) no . . . .
C32 O21 C33 C34 -73.2(14) no . . . .
C33 O21 C32 C24 51.8(15) no . . . .
N3 N2 C1 Se1 175.1(9) no . . . .
N3 N2 C1 N5 0.6(13) no . . . .
C1 N2 N3 C4 0.8(13) no . . . .
N3 N2 C6 C7 152.9(10) no . . . .
N3 N2 C6 C11 -26.5(16) no . . . .
C6 N2 N3 C4 176.1(10) no . . . .
C1 N2 C6 C7 -32.6(19) no . . . .
C1 N2 C6 C11 148.0(12) no . . . .
C6 N2 C1 Se1 0(2) no . . . .
C6 N2 C1 N5 -174.1(11) no . . . .
N2 N3 C4 N5 -1.9(14) no . . . .
N2 N3 C4 C12 -177.9(11) no . . . .
C1 N5 C4 N3 2.4(15) no . . . .
C1 N5 C4 C12 178.8(10) no . . . .
C4 N5 C1 Se1 -176.8(9) no . . . .
C4 N5 C1 N2 -1.7(13) no . . . .
C1 N5 C14 C13 -165.3(10) no . . . .
C14 N5 C1 Se1 6.1(18) no . . . .
C14 N5 C1 N2 -178.8(11) no . . . .
C4 N5 C14 C13 18.1(17) no . . . .
C14 N5 C4 N3 179.6(11) no . . . .
C14 N5 C4 C12 -4.0(19) no . . . .
N23 N22 C21 Se21 -176.9(10) no . . . .
N23 N22 C21 N25 1.7(15) no . . . .
C21 N22 N23 C24 -0.9(14) no . . . .
N23 N22 C26 C27 -138.9(11) no . . . .
N23 N22 C26 C31 41.3(16) no . . . .
C26 N22 N23 C24 -177.9(10) no . . . .
C21 N22 C26 C27 45(2) no . . . .
C21 N22 C26 C31 -134.9(14) no . . . .
C26 N22 C21 Se21 -0(2) no . . . .
C26 N22 C21 N25 178.1(12) no . . . .
N22 N23 C24 N25 -0.2(14) no . . . .
N22 N23 C24 C32 176.2(12) no . . . .
C21 N25 C24 N23 1.3(16) no . . . .
C21 N25 C24 C32 -175.4(11) no . . . .
C24 N25 C21 Se21 176.8(11) no . . . .
C24 N25 C21 N22 -1.8(15) no . . . .
C21 N25 C34 C33 159.2(13) no . . . .
C34 N25 C21 Se21 1(2) no . . . .
C34 N25 C21 N22 -177.9(12) no . . . .
C24 N25 C34 C33 -16.5(17) no . . . .
C34 N25 C24 N23 177.6(11) no . . . .
C34 N25 C24 C32 0.9(19) no . . . .
N3 C4 C12 O1 -165.0(13) no . . . .
N5 C4 C12 O1 19.2(16) no . . . .
N2 C6 C7 C8 177.2(11) no . . . .
N2 C6 C11 C10 -178.3(11) no . . . .
C7 C6 C11 C10 2(2) no . . . .
C11 C6 C7 C8 -3(2) no . . . .
C6 C7 C8 C9 2(2) no . . . .
C7 C8 C9 C10 0(2) no . . . .
C8 C9 C10 C11 -1(3) no . . . .
C9 C10 C11 C6 0(3) no . . . .
O1 C13 C14 N5 -47.9(17) no . . . .
N23 C24 C32 O21 166.0(13) no . . . .
N25 C24 C32 O21 -17.9(19) no . . . .
N22 C26 C27 C28 -179.3(12) no . . . .
N22 C26 C31 C30 177.1(11) no . . . .
C27 C26 C31 C30 -3(2) no . . . .
C31 C26 C27 C28 0(2) no . . . .
C26 C27 C28 C29 2(2) no . . . .
C27 C28 C29 C30 -1(2) no . . . .
C28 C29 C30 C31 -1(3) no . . . .
C29 C30 C31 C26 3(2) no . . . .
O21 C33 C34 N25 51.8(15) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Se1 C6 3.495(14) no . .
Se1 C7 3.343(16) no . .
Se1 C14 3.318(16) no . .
Se21 C26 3.451(14) no . .
Se21 C27 3.461(19) no . .
Se21 C34 3.360(17) no . .
O1 N5 2.727(17) no . .
O21 N25 2.736(17) no . .
N2 C14 3.546(19) no . .
N3 C11 2.82(2) no . .
N3 C14 3.589(19) no . .
N5 C6 3.56(2) no . .
N22 C34 3.574(19) no . .
N23 C27 3.59(2) no . .
N23 C31 2.85(2) no . .
N23 C34 3.595(18) no . .
N25 C26 3.52(2) no . .
C1 C7 3.05(2) no . .
C4 C6 3.46(2) no . .
C4 C13 2.75(2) no . .
C6 C9 2.75(3) no . .
C7 C10 2.78(2) no . .
C8 C11 2.79(3) no . .
C12 C14 2.94(2) no . .
C21 C27 3.17(3) no . .
C24 C26 3.46(2) no . .
C24 C33 2.70(2) no . .
C26 C29 2.77(3) no . .
C27 C30 2.76(3) no . .
C28 C31 2.78(2) no . .
C32 C34 2.94(2) no . .
Se1 C4 3.549(14) no . 2_656
Se21 C24 3.570(14) no . 2_565
O1 N2 3.134(16) no . 2_666
O1 C1 3.274(16) no . 2_666
O1 C6 3.520(19) no . 2_666
O1 C7 3.45(2) no . 2_666
O1 C12 3.317(16) no . 2_766
O21 N22 3.312(16) no . 2_665
O21 C21 3.389(19) no . 2_665
O21 C26 3.588(18) no . 2_665
O21 C27 3.21(2) no . 2_665
O21 C32 3.388(18) no . 2_675
N2 O1 3.134(16) no . 2_666
N3 C14 3.480(19) no . 2_666
N3 C30 3.60(2) no . 2_666
N5 C4 3.448(18) no . 2_666
N22 O21 3.312(16) no . 2_665
N23 C10 3.57(2) no . 2_666
N23 C34 3.529(19) no . 2_665
N25 C24 3.482(18) no . 2_665
C1 O1 3.274(16) no . 2_666
C1 C12 3.466(18) no . 2_666
C4 Se1 3.549(14) no . 2_656
C4 N5 3.448(18) no . 2_666
C6 O1 3.520(19) no . 2_666
C7 O1 3.45(2) no . 2_666
C10 N23 3.57(2) no . 2_666
C12 O1 3.317(16) no . 2_766
C12 C1 3.466(18) no . 2_666
C12 C12 3.275(19) no . 2_766
C14 N3 3.480(19) no . 2_666
C21 O21 3.389(19) no . 2_665
C24 Se21 3.570(14) no . 2_565
C24 N25 3.482(18) no . 2_665
C26 O21 3.588(18) no . 2_665
C27 O21 3.21(2) no . 2_665
C30 N3 3.60(2) no . 2_666
C31 C34 3.60(2) no . 2_565
C32 O21 3.388(18) no . 2_675
C32 C32 3.34(2) no . 2_675
C34 N23 3.529(19) no . 2_665
C34 C31 3.60(2) no . 2_565
Se1 H7 2.7667 no . .
Se1 H14A 3.4691 no . .
Se1 H14B 3.0353 no . .
Se21 H27 3.0200 no . .
Se21 H34A 3.0727 no . .
Se21 H34B 3.5541 no . .
O1 H14A 2.7608 no . .
O1 H14B 3.2875 no . .
O21 H34A 3.2608 no . .
O21 H34B 2.7014 no . .
N2 H7 2.6279 no . .
N2 H11 2.6129 no . .
N3 H11 2.5111 no . .
N3 H12A 2.7785 no . .
N3 H12B 2.9225 no . .
N5 H12A 3.2235 no . .
N5 H12B 3.0214 no . .
N5 H13A 2.6984 no . .
N5 H13B 3.2543 no . .
N22 H27 2.6562 no . .
N22 H31 2.5907 no . .
N23 H31 2.6096 no . .
N23 H32A 2.8967 no . .
N23 H32B 2.7574 no . .
N25 H32A 3.0235 no . .
N25 H32B 3.2082 no . .
N25 H33A 3.2566 no . .
N25 H33B 2.6517 no . .
C1 H7 2.8242 no . .
C1 H14A 2.9153 no . .
C1 H14B 2.7541 no . .
C4 H13A 2.9366 no . .
C4 H14A 3.0371 no . .
C4 H14B 3.2141 no . .
C6 H8 3.2513 no . .
C6 H10 3.2562 no . .
C7 H9 3.2596 no . .
C7 H11 3.2733 no . .
C8 H10 3.2609 no . .
C9 H7 3.2657 no . .
C9 H11 3.2540 no . .
C10 H8 3.2589 no . .
C11 H7 3.2725 no . .
C11 H9 3.2512 no . .
C12 H13A 2.4995 no . .
C12 H13B 3.1650 no . .
C12 H14A 3.4425 no . .
C13 H12A 3.1826 no . .
C13 H12B 2.6143 no . .
C14 H12B 3.4298 no . .
C21 H27 3.0118 no . .
C21 H34A 2.7087 no . .
C21 H34B 2.9209 no . .
C24 H33B 2.8143 no . .
C24 H34A 3.2085 no . .
C24 H34B 3.0415 no . .
C26 H28 3.2397 no . .
C26 H30 3.2498 no . .
C27 H29 3.2488 no . .
C27 H31 3.2895 no . .
C28 H30 3.2298 no . .
C29 H27 3.2497 no . .
C29 H31 3.2690 no . .
C30 H28 3.2301 no . .
C31 H27 3.2863 no . .
C31 H29 3.2677 no . .
C32 H33A 3.1746 no . .
C32 H33B 2.4313 no . .
C32 H34B 3.4389 no . .
C33 H32A 2.5969 no . .
C33 H32B 3.1832 no . .
C34 H32A 3.4247 no . .
H7 H8 2.3472 no . .
H8 H9 2.3418 no . .
H9 H10 2.3119 no . .
H10 H11 2.3534 no . .
H12A H13A 3.4410 no . .
H12B H13A 2.3993 no . .
H12B H13B 3.4354 no . .
H13A H14A 2.8640 no . .
H13A H14B 2.3079 no . .
H13B H14A 2.3168 no . .
H13B H14B 2.4383 no . .
H27 H28 2.3071 no . .
H28 H29 2.3303 no . .
H29 H30 2.3170 no . .
H30 H31 2.3378 no . .
H32A H33A 3.4123 no . .
H32A H33B 2.3187 no . .
H32B H33B 3.3807 no . .
H33A H34A 2.3962 no . .
H33A H34B 2.3176 no . .
H33B H34A 2.3068 no . .
H33B H34B 2.8516 no . .
Se1 H7 3.4349 no . 2_556
Se1 H8 3.4012 no . 2_556
Se1 H12A 3.1616 no . 2_666
Se1 H12B 3.3209 no . 1_455
Se1 H12B 3.5735 no . 2_656
Se1 H13A 3.4945 no . 1_455
Se1 H29 3.0658 no . .
Se21 H9 3.2202 no . 1_554
Se21 H32A 2.9997 no . 1_545
Se21 H32A 3.3842 no . 2_565
Se21 H32B 3.1601 no . 2_665
Se21 H33B 3.5646 no . 1_545
Se21 H33B 3.2422 no . 2_565
O1 H7 3.0419 no . 2_666
O1 H12A 2.8827 no . 2_766
O1 H12B 2.9034 no . 2_766
O1 H29 3.5881 no . 1_655
O1 H30 3.2649 no . 1_655
O21 H27 2.5783 no . 2_665
O21 H32A 3.1492 no . 2_675
O21 H32B 2.7868 no . 2_675
N2 H14A 3.3698 no . 2_666
N2 H14B 3.3084 no . 2_656
N3 H14A 2.6815 no . 2_666
N3 H30 3.3277 no . 2_666
N5 H12A 3.3397 no . 2_666
N22 H34A 3.2092 no . 2_565
N22 H34B 3.1785 no . 2_665
N23 H10 2.9058 no . 2_666
N23 H34B 2.6792 no . 2_665
N25 H32B 3.5913 no . 2_665
C1 H12A 2.9939 no . 2_666
C4 H14A 3.0618 no . 2_666
C6 H13A 3.3994 no . 2_656
C6 H14B 2.8956 no . 2_656
C7 H12B 3.3827 no . 1_455
C7 H13A 3.0337 no . 2_656
C7 H14B 3.5112 no . 2_656
C7 H30 3.1123 no . 2_566
C8 H13A 3.1270 no . 2_656
C8 H28 3.4518 no . 2_556
C8 H29 3.2843 no . 2_556
C8 H30 3.0739 no . 2_566
C8 H31 3.0679 no . 2_566
C9 H31 3.3622 no . 2_566
C9 H34A 3.4282 no . 1_556
C9 H34B 3.3853 no . 1_556
C10 H14B 3.3314 no . 2_656
C10 H28 3.4674 no . 2_656
C10 H34B 3.0859 no . 1_556
C11 H14B 2.8130 no . 2_656
C11 H28 3.3810 no . 2_656
C12 H7 3.3785 no . 1_655
C12 H12A 2.9882 no . 2_766
C12 H12B 3.0081 no . 2_766
C12 H14A 3.5901 no . 2_666
C12 H30 3.4616 no . 2_666
C13 H29 3.2174 no . 1_655
C13 H30 3.5106 no . 1_655
C21 H32B 3.2397 no . 2_665
C24 H10 3.4518 no . 2_666
C24 H34B 3.0901 no . 2_665
C26 H33B 3.3548 no . 2_565
C26 H34A 2.9848 no . 2_565
C27 H32A 3.4908 no . 1_545
C27 H33B 3.3622 no . 2_565
C28 H8 3.3172 no . 2_556
C28 H9 3.3970 no . 2_556
C28 H14A 3.5345 no . .
C29 H8 3.3633 no . 2_556
C29 H12A 3.5431 no . 2_666
C29 H13A 3.5908 no . 1_455
C29 H13B 3.2684 no . 1_455
C29 H14A 3.1383 no . .
C30 H8 3.5353 no . 2_566
C30 H12A 3.4975 no . 2_666
C30 H13B 3.3262 no . 1_455
C30 H14A 3.5443 no . .
C30 H34A 3.3462 no . 2_565
C31 H8 3.3845 no . 2_566
C31 H11 3.2930 no . 2_666
C31 H34A 2.6807 no . 2_565
C32 H10 3.4246 no . 2_666
C32 H27 3.3131 no . 1_565
C32 H32A 3.2492 no . 2_675
C32 H32B 2.8994 no . 2_675
C33 H27 3.5905 no . 2_665
C34 H31 3.5979 no . 2_565
H7 Se1 3.4349 no . 2_556
H7 O1 3.0419 no . 2_666
H7 C12 3.3785 no . 1_455
H7 H12A 3.5909 no . 1_455
H7 H12A 3.5349 no . 2_666
H7 H12B 2.4739 no . 1_455
H7 H13A 3.2744 no . 2_656
H7 H30 3.0110 no . 2_566
H8 Se1 3.4012 no . 2_556
H8 C28 3.3172 no . 2_556
H8 C29 3.3633 no . 2_556
H8 C30 3.5353 no . 2_566
H8 C31 3.3845 no . 2_566
H8 H11 3.2483 no . 1_455
H8 H13A 3.3944 no . 2_656
H8 H28 2.7319 no . 2_556
H8 H29 2.8305 no . 2_556
H8 H30 2.9681 no . 2_566
H8 H31 2.6807 no . 2_566
H9 Se21 3.2202 no . 1_556
H9 C28 3.3970 no . 2_556
H9 H28 3.1380 no . 2_556
H9 H31 3.2178 no . 2_566
H9 H33A 3.2160 no . 1_546
H9 H33B 3.2724 no . 1_546
H9 H34A 3.3001 no . 1_556
H9 H34B 3.4525 no . 1_556
H10 N23 2.9058 no . 2_666
H10 C24 3.4518 no . 2_666
H10 C32 3.4246 no . 2_666
H10 H27 3.3685 no . 2_656
H10 H28 3.0349 no . 2_656
H10 H32B 2.7654 no . 2_666
H10 H33A 3.5946 no . 1_546
H10 H34B 2.9235 no . 1_556
H11 C31 3.2930 no . 2_666
H11 H8 3.2483 no . 1_655
H11 H14B 2.9943 no . 2_656
H11 H28 2.8730 no . 2_656
H11 H31 2.9036 no . 2_666
H12A Se1 3.1616 no . 2_666
H12A O1 2.8827 no . 2_766
H12A N5 3.3397 no . 2_666
H12A C1 2.9939 no . 2_666
H12A C12 2.9882 no . 2_766
H12A C29 3.5431 no . 2_666
H12A C30 3.4975 no . 2_666
H12A H7 3.5909 no . 1_655
H12A H7 3.5349 no . 2_666
H12A H12A 3.0149 no . 2_766
H12A H12B 2.5777 no . 2_766
H12A H13A 3.5852 no . 2_766
H12A H14A 3.0974 no . 2_666
H12A H29 3.0516 no . 2_666
H12A H30 2.9516 no . 2_666
H12B Se1 3.3209 no . 1_655
H12B Se1 3.5735 no . 2_656
H12B O1 2.9034 no . 2_766
H12B C7 3.3827 no . 1_655
H12B C12 3.0081 no . 2_766
H12B H7 2.4739 no . 1_655
H12B H12A 2.5777 no . 2_766
H12B H12B 3.0543 no . 2_766
H12B H30 3.2934 no . 2_666
H13A Se1 3.4945 no . 1_655
H13A C6 3.3994 no . 2_656
H13A C7 3.0337 no . 2_656
H13A C8 3.1270 no . 2_656
H13A C29 3.5908 no . 1_655
H13A H7 3.2744 no . 2_656
H13A H8 3.3944 no . 2_656
H13A H12A 3.5852 no . 2_766
H13A H29 2.8251 no . 1_655
H13B C29 3.2684 no . 1_655
H13B C30 3.3262 no . 1_655
H13B H29 2.8781 no . 1_655
H13B H30 2.9636 no . 1_655
H13B H33A 3.1590 no . 2_665
H14A N2 3.3698 no . 2_666
H14A N3 2.6815 no . 2_666
H14A C4 3.0618 no . 2_666
H14A C12 3.5901 no . 2_666
H14A C28 3.5345 no . .
H14A C29 3.1383 no . .
H14A C30 3.5443 no . .
H14A H12A 3.0974 no . 2_666
H14A H29 3.1134 no . .
H14B N2 3.3084 no . 2_656
H14B C6 2.8956 no . 2_656
H14B C7 3.5112 no . 2_656
H14B C10 3.3314 no . 2_656
H14B C11 2.8130 no . 2_656
H14B H11 2.9943 no . 2_656
H14B H28 3.3918 no . .
H14B H29 3.4363 no . .
H27 O21 2.5783 no . 2_665
H27 C32 3.3131 no . 1_545
H27 C33 3.5905 no . 2_665
H27 H10 3.3685 no . 2_656
H27 H32A 2.5827 no . 1_545
H27 H32B 3.1891 no . 1_545
H27 H32B 3.4731 no . 2_665
H27 H33A 3.4730 no . 2_665
H28 C8 3.4518 no . 2_556
H28 C10 3.4674 no . 2_656
H28 C11 3.3810 no . 2_656
H28 H8 2.7319 no . 2_556
H28 H9 3.1380 no . 2_556
H28 H10 3.0349 no . 2_656
H28 H11 2.8730 no . 2_656
H28 H14B 3.3918 no . .
H28 H31 3.4677 no . 1_545
H29 Se1 3.0658 no . .
H29 O1 3.5881 no . 1_455
H29 C8 3.2843 no . 2_556
H29 C13 3.2174 no . 1_455
H29 H8 2.8305 no . 2_556
H29 H12A 3.0516 no . 2_666
H29 H13A 2.8251 no . 1_455
H29 H13B 2.8781 no . 1_455
H29 H14A 3.1134 no . .
H29 H14B 3.4363 no . .
H30 O1 3.2649 no . 1_455
H30 N3 3.3277 no . 2_666
H30 C7 3.1123 no . 2_566
H30 C8 3.0739 no . 2_566
H30 C12 3.4616 no . 2_666
H30 C13 3.5106 no . 1_455
H30 H7 3.0110 no . 2_566
H30 H8 2.9681 no . 2_566
H30 H12A 2.9516 no . 2_666
H30 H12B 3.2934 no . 2_666
H30 H13B 2.9636 no . 1_455
H31 C8 3.0679 no . 2_566
H31 C9 3.3622 no . 2_566
H31 C34 3.5979 no . 2_565
H31 H8 2.6807 no . 2_566
H31 H9 3.2178 no . 2_566
H31 H11 2.9036 no . 2_666
H31 H28 3.4677 no . 1_565
H31 H34A 2.6199 no . 2_565
H32A Se21 2.9997 no . 1_565
H32A Se21 3.3842 no . 2_565
H32A O21 3.1492 no . 2_675
H32A C27 3.4908 no . 1_565
H32A C32 3.2492 no . 2_675
H32A H27 2.5827 no . 1_565
H32A H32A 3.4513 no . 2_675
H32A H32B 2.6815 no . 2_675
H32B Se21 3.1601 no . 2_665
H32B O21 2.7868 no . 2_675
H32B N25 3.5913 no . 2_665
H32B C21 3.2397 no . 2_665
H32B C32 2.8994 no . 2_675
H32B H10 2.7654 no . 2_666
H32B H27 3.1891 no . 1_565
H32B H27 3.4731 no . 2_665
H32B H32A 2.6815 no . 2_675
H32B H32B 2.7587 no . 2_675
H32B H34B 3.3492 no . 2_665
H33A H9 3.2160 no . 1_564
H33A H10 3.5946 no . 1_564
H33A H13B 3.1590 no . 2_665
H33A H27 3.4730 no . 2_665
H33B Se21 3.5646 no . 1_565
H33B Se21 3.2422 no . 2_565
H33B C26 3.3548 no . 2_565
H33B C27 3.3622 no . 2_565
H33B H9 3.2724 no . 1_564
H34A N22 3.2092 no . 2_565
H34A C9 3.4282 no . 1_554
H34A C26 2.9848 no . 2_565
H34A C30 3.3462 no . 2_565
H34A C31 2.6807 no . 2_565
H34A H9 3.3001 no . 1_554
H34A H31 2.6199 no . 2_565
H34B N22 3.1785 no . 2_665
H34B N23 2.6792 no . 2_665
H34B C9 3.3853 no . 1_554
H34B C10 3.0859 no . 1_554
H34B C24 3.0901 no . 2_665
H34B H9 3.4525 no . 1_554
H34B H10 2.9235 no . 1_554
H34B H32B 3.3492 no . 2_665

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_chemical_name_systematic        '[Se(Tr3)]'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone, hexane'
####################################################################### 
# 
# 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_[Se(Tr4)]
_database_code_depnum_ccdc_archive 'CCDC 1024817'
_audit_update_record             
;
2014-09-17 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21 H21 N3 O Se'
_chemical_formula_moiety         'C21 H21 N3 O Se'
_chemical_formula_weight         410.38
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.5326(19)
_cell_length_b                   10.637(3)
_cell_length_c                   11.589(3)
_cell_angle_alpha                107.558(4)
_cell_angle_beta                 101.546(4)
_cell_angle_gamma                107.498(3)
_cell_volume                     906.2(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3229
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      25.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420.00
_exptl_absorpt_coefficient_mu    2.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_T_max  0.920

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 11.628
_diffrn_reflns_number            11092
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_theta_max         25.378
_diffrn_reflns_theta_min         1.945
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3280
_reflns_number_gt                2944
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0546
_refine_ls_wR_factor_gt          0.0542
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3280
_refine_ls_number_parameters     238
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0191P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 1.09830(3) 0.37296(2) 0.07155(2) 0.02361(7) Uani 1 2 d . . .
O1 O 0.68846(17) 0.61454(14) 0.28632(12) 0.0258(3) Uani 1 2 d . . .
N2 N 0.7274(2) 0.24928(16) 0.00092(15) 0.0234(3) Uani 1 2 d . . .
N3 N 0.5865(2) 0.27778(17) 0.02623(16) 0.0272(4) Uani 1 2 d . . .
N5 N 0.8347(2) 0.45713(15) 0.15014(14) 0.0200(3) Uani 1 2 d . . .
C1 C 0.8800(3) 0.35756(19) 0.07374(18) 0.0205(4) Uani 1 2 d . . .
C4 C 0.6584(3) 0.4051(2) 0.11655(18) 0.0231(4) Uani 1 2 d . . .
C6 C 0.7043(2) 0.11875(19) -0.09851(18) 0.0225(4) Uani 1 2 d . . .
C7 C 0.7448(3) 0.0150(2) -0.06343(19) 0.0256(4) Uani 1 2 d . . .
C8 C 0.7359(3) -0.1039(2) -0.1606(2) 0.0284(5) Uani 1 2 d . . .
C9 C 0.6888(3) -0.1213(2) -0.2879(2) 0.0268(4) Uani 1 2 d . . .
C10 C 0.6431(3) -0.0177(2) -0.3181(2) 0.0263(4) Uani 1 2 d . . .
C11 C 0.6490(3) 0.10354(19) -0.22518(19) 0.0244(4) Uani 1 2 d . . .
C12 C 0.7941(3) 0.0291(2) 0.0734(2) 0.0350(5) Uani 1 2 d . . .
C13 C 0.6872(3) -0.2500(2) -0.3896(2) 0.0375(5) Uani 1 2 d . . .
C14 C 0.5923(3) 0.2108(2) -0.2624(2) 0.0324(5) Uani 1 2 d . . .
C15 C 0.5685(3) 0.4944(2) 0.1772(2) 0.0286(5) Uani 1 2 d . . .
C16 C 0.8357(3) 0.6935(2) 0.25931(19) 0.0254(4) Uani 1 2 d . . .
C17 C 0.9512(3) 0.8209(2) 0.38303(19) 0.0288(5) Uani 1 2 d . . .
C18 C 1.0580(3) 0.7594(2) 0.45205(19) 0.0270(4) Uani 1 2 d . . .
C19 C 1.1535(3) 0.8120(2) 0.5801(2) 0.0321(5) Uani 1 2 d . . .
C20 C 1.2401(3) 0.7343(2) 0.6222(2) 0.0356(5) Uani 1 2 d . . .
C21 C 1.2305(3) 0.6063(2) 0.5376(2) 0.0329(5) Uani 1 2 d . . .
C22 C 1.1373(3) 0.5545(2) 0.4090(2) 0.0267(4) Uani 1 2 d . . .
C23 C 1.0517(3) 0.63204(19) 0.36741(18) 0.0230(4) Uani 1 2 d . . .
C24 C 0.9472(3) 0.60516(18) 0.23446(18) 0.0217(4) Uani 1 2 d . . .
H8 H 0.763 -0.17613 -0.13934 0.0341 Uiso 1 2 calc R . .
H10 H 0.60659 -0.03011 -0.40527 0.0316 Uiso 1 2 calc R . .
H12A H 0.82793 -0.0497 0.07895 0.0420 Uiso 1 2 calc R . .
H12B H 0.69485 0.02578 0.10449 0.0420 Uiso 1 2 calc R . .
H12C H 0.89166 0.12038 0.12584 0.0420 Uiso 1 2 calc R . .
H13A H 0.80587 -0.23541 -0.39055 0.0450 Uiso 1 2 calc R . .
H13B H 0.61544 -0.26327 -0.47316 0.0450 Uiso 1 2 calc R . .
H13C H 0.63916 -0.33514 -0.37129 0.0450 Uiso 1 2 calc R . .
H14A H 0.67252 0.30774 -0.20364 0.0388 Uiso 1 2 calc R . .
H14B H 0.47506 0.19662 -0.25789 0.0388 Uiso 1 2 calc R . .
H14C H 0.59234 0.19792 -0.34971 0.0388 Uiso 1 2 calc R . .
H15A H 0.51205 0.52672 0.11503 0.0343 Uiso 1 2 calc R . .
H15B H 0.47728 0.43632 0.20226 0.0343 Uiso 1 2 calc R . .
H16 H 0.8011 0.72337 0.1874 0.0304 Uiso 1 2 calc R . .
H17A H 1.02578 0.89976 0.36576 0.0346 Uiso 1 2 calc R . .
H17B H 0.88113 0.85673 0.43304 0.0346 Uiso 1 2 calc R . .
H19 H 1.15982 0.89976 0.63807 0.0385 Uiso 1 2 calc R . .
H20 H 1.30626 0.76932 0.70975 0.0427 Uiso 1 2 calc R . .
H21 H 1.28845 0.55336 0.56792 0.0395 Uiso 1 2 calc R . .
H22 H 1.13244 0.46748 0.35074 0.0320 Uiso 1 2 calc R . .
H24 H 1.02789 0.64571 0.19132 0.0260 Uiso 1 2 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Se1 C1 1.827(2) yes . .
O1 C15 1.4143(19) yes . .
O1 C16 1.436(3) yes . .
N2 N3 1.390(3) yes . .
N2 C1 1.344(2) yes . .
N2 C6 1.440(2) yes . .
N3 C4 1.302(2) yes . .
N5 C1 1.368(3) yes . .
N5 C4 1.362(3) yes . .
N5 C24 1.4639(19) yes . .
C4 C15 1.496(3) yes . .
C6 C7 1.395(3) yes . .
C6 C11 1.392(3) yes . .
C7 C8 1.387(3) yes . .
C7 C12 1.505(3) yes . .
C8 C9 1.388(3) yes . .
C9 C10 1.388(4) yes . .
C9 C13 1.508(3) yes . .
C10 C11 1.388(3) yes . .
C11 C14 1.506(4) yes . .
C16 C17 1.524(2) yes . .
C16 C24 1.534(3) yes . .
C17 C18 1.510(4) yes . .
C18 C19 1.385(3) yes . .
C18 C23 1.391(3) yes . .
C19 C20 1.390(4) yes . .
C20 C21 1.385(3) yes . .
C21 C22 1.387(3) yes . .
C22 C23 1.381(3) yes . .
C23 C24 1.511(3) yes . .
C8 H8 0.950 no . .
C10 H10 0.950 no . .
C12 H12A 0.980 no . .
C12 H12B 0.980 no . .
C12 H12C 0.980 no . .
C13 H13A 0.980 no . .
C13 H13B 0.980 no . .
C13 H13C 0.980 no . .
C14 H14A 0.980 no . .
C14 H14B 0.980 no . .
C14 H14C 0.980 no . .
C15 H15A 0.990 no . .
C15 H15B 0.990 no . .
C16 H16 1.000 no . .
C17 H17A 0.990 no . .
C17 H17B 0.990 no . .
C19 H19 0.950 no . .
C20 H20 0.950 no . .
C21 H21 0.950 no . .
C22 H22 0.950 no . .
C24 H24 1.000 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C15 O1 C16 112.26(16) yes . . .
N3 N2 C1 112.79(16) yes . . .
N3 N2 C6 121.43(13) yes . . .
C1 N2 C6 125.70(19) yes . . .
N2 N3 C4 103.22(15) yes . . .
C1 N5 C4 107.94(13) yes . . .
C1 N5 C24 127.22(17) yes . . .
C4 N5 C24 123.72(18) yes . . .
Se1 C1 N2 128.93(16) yes . . .
Se1 C1 N5 127.20(11) yes . . .
N2 C1 N5 103.86(18) yes . . .
N3 C4 N5 112.2(2) yes . . .
N3 C4 C15 127.16(18) yes . . .
N5 C4 C15 120.62(14) yes . . .
N2 C6 C7 118.45(18) yes . . .
N2 C6 C11 118.8(2) yes . . .
C7 C6 C11 122.74(18) yes . . .
C6 C7 C8 117.1(2) yes . . .
C6 C7 C12 122.04(19) yes . . .
C8 C7 C12 120.8(2) yes . . .
C7 C8 C9 122.4(2) yes . . .
C8 C9 C10 118.18(19) yes . . .
C8 C9 C13 120.3(2) yes . . .
C10 C9 C13 121.5(2) yes . . .
C9 C10 C11 122.1(2) yes . . .
C6 C11 C10 117.4(2) yes . . .
C6 C11 C14 122.18(18) yes . . .
C10 C11 C14 120.4(2) yes . . .
O1 C15 C4 110.37(17) yes . . .
O1 C16 C17 106.79(18) yes . . .
O1 C16 C24 109.25(17) yes . . .
C17 C16 C24 103.63(17) yes . . .
C16 C17 C18 102.99(17) yes . . .
C17 C18 C19 129.4(2) yes . . .
C17 C18 C23 110.47(17) yes . . .
C19 C18 C23 120.2(2) yes . . .
C18 C19 C20 118.9(2) yes . . .
C19 C20 C21 120.5(2) yes . . .
C20 C21 C22 120.8(3) yes . . .
C21 C22 C23 118.6(2) yes . . .
C18 C23 C22 121.08(18) yes . . .
C18 C23 C24 108.7(2) yes . . .
C22 C23 C24 130.21(18) yes . . .
N5 C24 C16 109.35(15) yes . . .
N5 C24 C23 117.48(18) yes . . .
C16 C24 C23 103.11(16) yes . . .
C7 C8 H8 118.825 no . . .
C9 C8 H8 118.822 no . . .
C9 C10 H10 118.939 no . . .
C11 C10 H10 118.945 no . . .
C7 C12 H12A 109.472 no . . .
C7 C12 H12B 109.469 no . . .
C7 C12 H12C 109.471 no . . .
H12A C12 H12B 109.469 no . . .
H12A C12 H12C 109.470 no . . .
H12B C12 H12C 109.477 no . . .
C9 C13 H13A 109.474 no . . .
C9 C13 H13B 109.467 no . . .
C9 C13 H13C 109.474 no . . .
H13A C13 H13B 109.468 no . . .
H13A C13 H13C 109.470 no . . .
H13B C13 H13C 109.473 no . . .
C11 C14 H14A 109.470 no . . .
C11 C14 H14B 109.473 no . . .
C11 C14 H14C 109.471 no . . .
H14A C14 H14B 109.473 no . . .
H14A C14 H14C 109.475 no . . .
H14B C14 H14C 109.466 no . . .
O1 C15 H15A 109.577 no . . .
O1 C15 H15B 109.579 no . . .
C4 C15 H15A 109.582 no . . .
C4 C15 H15B 109.578 no . . .
H15A C15 H15B 108.118 no . . .
O1 C16 H16 112.234 no . . .
C17 C16 H16 112.233 no . . .
C24 C16 H16 112.231 no . . .
C16 C17 H17A 111.171 no . . .
C16 C17 H17B 111.166 no . . .
C18 C17 H17A 111.166 no . . .
C18 C17 H17B 111.165 no . . .
H17A C17 H17B 109.101 no . . .
C18 C19 H19 120.539 no . . .
C20 C19 H19 120.547 no . . .
C19 C20 H20 119.766 no . . .
C21 C20 H20 119.762 no . . .
C20 C21 H21 119.624 no . . .
C22 C21 H21 119.613 no . . .
C21 C22 H22 120.702 no . . .
C23 C22 H22 120.706 no . . .
N5 C24 H24 108.849 no . . .
C16 C24 H24 108.850 no . . .
C23 C24 H24 108.848 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C15 O1 C16 C17 178.60(16) no . . . .
C15 O1 C16 C24 -69.9(2) no . . . .
C16 O1 C15 C4 52.0(2) no . . . .
N3 N2 C1 Se1 -177.55(17) no . . . .
N3 N2 C1 N5 1.4(2) no . . . .
C1 N2 N3 C4 -0.5(2) no . . . .
N3 N2 C6 C7 -107.7(2) no . . . .
N3 N2 C6 C11 74.7(2) no . . . .
C6 N2 N3 C4 -177.51(17) no . . . .
C1 N2 C6 C7 75.7(3) no . . . .
C1 N2 C6 C11 -101.9(2) no . . . .
C6 N2 C1 Se1 -0.7(4) no . . . .
C6 N2 C1 N5 178.27(19) no . . . .
N2 N3 C4 N5 -0.7(2) no . . . .
N2 N3 C4 C15 176.44(19) no . . . .
C1 N5 C4 N3 1.6(3) no . . . .
C1 N5 C4 C15 -175.75(18) no . . . .
C4 N5 C1 Se1 177.24(18) no . . . .
C4 N5 C1 N2 -1.7(2) no . . . .
C1 N5 C24 C16 157.47(19) no . . . .
C1 N5 C24 C23 -85.6(3) no . . . .
C24 N5 C1 Se1 9.1(3) no . . . .
C24 N5 C1 N2 -169.86(18) no . . . .
C4 N5 C24 C16 -8.9(3) no . . . .
C4 N5 C24 C23 108.1(2) no . . . .
C24 N5 C4 N3 170.22(17) no . . . .
C24 N5 C4 C15 -7.1(3) no . . . .
N3 C4 C15 O1 169.6(2) no . . . .
N5 C4 C15 O1 -13.5(3) no . . . .
N2 C6 C7 C8 -174.49(15) no . . . .
N2 C6 C7 C12 6.3(3) no . . . .
N2 C6 C11 C10 174.29(15) no . . . .
N2 C6 C11 C14 -7.4(3) no . . . .
C7 C6 C11 C10 -3.2(3) no . . . .
C7 C6 C11 C14 175.09(16) no . . . .
C11 C6 C7 C8 3.0(3) no . . . .
C11 C6 C7 C12 -176.24(16) no . . . .
C6 C7 C8 C9 -0.1(3) no . . . .
C12 C7 C8 C9 179.18(17) no . . . .
C7 C8 C9 C10 -2.5(3) no . . . .
C7 C8 C9 C13 177.83(17) no . . . .
C8 C9 C10 C11 2.3(3) no . . . .
C13 C9 C10 C11 -178.04(17) no . . . .
C9 C10 C11 C6 0.5(3) no . . . .
C9 C10 C11 C14 -177.84(17) no . . . .
O1 C16 C17 C18 84.7(2) no . . . .
O1 C16 C24 N5 44.7(2) no . . . .
O1 C16 C24 C23 -81.00(14) no . . . .
C17 C16 C24 N5 158.28(16) no . . . .
C17 C16 C24 C23 32.5(2) no . . . .
C24 C16 C17 C18 -30.6(2) no . . . .
C16 C17 C18 C19 -162.2(2) no . . . .
C16 C17 C18 C23 17.7(2) no . . . .
C17 C18 C19 C20 178.9(2) no . . . .
C17 C18 C23 C22 -178.85(17) no . . . .
C17 C18 C23 C24 3.1(2) no . . . .
C19 C18 C23 C22 1.1(3) no . . . .
C19 C18 C23 C24 -176.97(18) no . . . .
C23 C18 C19 C20 -1.0(3) no . . . .
C18 C19 C20 C21 -0.1(3) no . . . .
C19 C20 C21 C22 1.2(4) no . . . .
C20 C21 C22 C23 -1.1(3) no . . . .
C21 C22 C23 C18 -0.0(3) no . . . .
C21 C22 C23 C24 177.55(19) no . . . .
C18 C23 C24 N5 -142.76(18) no . . . .
C18 C23 C24 C16 -22.5(2) no . . . .
C22 C23 C24 N5 39.4(3) no . . . .
C22 C23 C24 C16 159.7(2) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Se1 C6 3.3411(16) no . .
Se1 C24 3.377(2) no . .
O1 N5 2.702(2) no . .
O1 C18 2.979(2) no . .
O1 C23 2.984(3) no . .
N2 C12 2.883(4) no . .
N2 C14 2.891(3) no . .
N2 C15 3.582(3) no . .
N2 C24 3.562(2) no . .
N3 C7 3.435(3) no . .
N3 C11 3.189(3) no . .
N3 C14 3.216(3) no . .
N3 C24 3.596(2) no . .
N5 C6 3.542(2) no . .
N5 C22 3.187(3) no . .
C1 C7 3.222(3) no . .
C1 C11 3.406(2) no . .
C1 C12 3.346(3) no . .
C1 C23 3.419(2) no . .
C4 C6 3.489(3) no . .
C4 C16 2.754(2) no . .
C4 C23 3.540(2) no . .
C6 C9 2.767(3) no . .
C7 C10 2.786(3) no . .
C8 C11 2.782(4) no . .
C15 C24 2.941(3) no . .
C18 C21 2.763(4) no . .
C19 C22 2.800(3) no . .
C20 C23 2.757(3) no . .
Se1 C24 3.575(2) no . 2_765
O1 C13 3.597(3) no . 1_566
O1 C14 3.462(3) no . 2_665
N3 C12 3.519(3) no . 2_655
C9 C20 3.465(3) no . 1_444
C10 C20 3.429(3) no . 1_444
C12 N3 3.519(3) no . 2_655
C13 O1 3.597(3) no . 1_544
C13 C21 3.543(3) no . 1_444
C14 O1 3.462(3) no . 2_665
C20 C9 3.465(3) no . 1_666
C20 C10 3.429(3) no . 1_666
C20 C22 3.585(3) no . 2_766
C21 C13 3.543(3) no . 1_666
C21 C22 3.369(3) no . 2_766
C21 C23 3.537(3) no . 2_766
C22 C20 3.585(3) no . 2_766
C22 C21 3.369(3) no . 2_766
C23 C21 3.537(3) no . 2_766
C24 Se1 3.575(2) no . 2_765
Se1 H12C 3.0559 no . .
Se1 H22 3.0080 no . .
Se1 H24 3.1076 no . .
O1 H17A 3.2155 no . .
O1 H17B 2.4335 no . .
O1 H24 3.2603 no . .
N2 H12B 2.9373 no . .
N2 H12C 2.7351 no . .
N2 H14A 2.6165 no . .
N2 H14B 3.1019 no . .
N3 H12B 3.3889 no . .
N3 H14A 2.9819 no . .
N3 H14B 3.0048 no . .
N3 H15A 2.8465 no . .
N3 H15B 2.7393 no . .
N5 H15A 3.0412 no . .
N5 H15B 3.1818 no . .
N5 H16 2.8439 no . .
N5 H22 3.0308 no . .
C1 H12B 3.5649 no . .
C1 H12C 2.7903 no . .
C1 H14A 3.1429 no . .
C1 H22 3.1250 no . .
C1 H24 2.7036 no . .
C4 H14A 3.5766 no . .
C4 H16 3.0102 no . .
C4 H24 3.1555 no . .
C6 H8 3.2337 no . .
C6 H10 3.2348 no . .
C6 H12A 3.3232 no . .
C6 H12B 2.8197 no . .
C6 H12C 2.7582 no . .
C6 H14A 2.6968 no . .
C6 H14B 2.8940 no . .
C6 H14C 3.3085 no . .
C8 H10 3.2378 no . .
C8 H12A 2.5589 no . .
C8 H12B 3.1035 no . .
C8 H12C 3.1670 no . .
C8 H13A 2.8812 no . .
C8 H13B 3.2870 no . .
C8 H13C 2.6531 no . .
C10 H8 3.2369 no . .
C10 H13A 3.0374 no . .
C10 H13B 2.5953 no . .
C10 H13C 3.2331 no . .
C10 H14A 3.2215 no . .
C10 H14B 3.0241 no . .
C10 H14C 2.5730 no . .
C12 H8 2.6564 no . .
C13 H8 2.6490 no . .
C13 H10 2.6743 no . .
C14 H10 2.6522 no . .
C15 H16 2.5910 no . .
C16 H15A 2.6430 no . .
C16 H15B 3.2160 no . .
C17 H19 2.8477 no . .
C17 H24 2.7670 no . .
C18 H16 3.2330 no . .
C18 H20 3.2498 no . .
C18 H22 3.2728 no . .
C18 H24 2.8207 no . .
C19 H17A 3.0254 no . .
C19 H17B 2.8459 no . .
C19 H21 3.2638 no . .
C20 H22 3.2693 no . .
C21 H19 3.2687 no . .
C22 H20 3.2636 no . .
C22 H24 3.0423 no . .
C23 H16 3.2486 no . .
C23 H17A 2.9272 no . .
C23 H17B 3.1379 no . .
C23 H19 3.2668 no . .
C23 H21 3.2392 no . .
C24 H15A 3.4320 no . .
C24 H17A 2.8347 no . .
C24 H17B 3.2379 no . .
C24 H22 2.8619 no . .
H8 H12A 2.3353 no . .
H8 H12B 3.2685 no . .
H8 H12C 3.3640 no . .
H8 H13A 2.9094 no . .
H8 H13B 3.5490 no . .
H8 H13C 2.4996 no . .
H10 H13A 3.1672 no . .
H10 H13B 2.3948 no . .
H10 H13C 3.4683 no . .
H10 H14A 3.4472 no . .
H10 H14B 3.1469 no . .
H10 H14C 2.3620 no . .
H12C H22 3.4835 no . .
H15A H16 2.4845 no . .
H15B H16 3.5244 no . .
H16 H17A 2.3193 no . .
H16 H17B 2.6049 no . .
H16 H24 2.3190 no . .
H17A H19 3.1341 no . .
H17A H24 2.8526 no . .
H17B H19 2.8173 no . .
H19 H20 2.3450 no . .
H20 H21 2.3267 no . .
H21 H22 2.3413 no . .
H22 H24 3.2053 no . .
Se1 H8 2.9175 no . 2_755
Se1 H14A 3.0616 no . 2_765
Se1 H15A 3.2727 no . 1_655
Se1 H15B 3.0526 no . 1_655
Se1 H16 3.2400 no . 2_765
Se1 H24 2.9449 no . 2_765
O1 H13A 3.3919 no . 1_566
O1 H13B 2.9738 no . 1_566
O1 H14A 3.4520 no . 2_665
O1 H14B 2.8268 no . 2_665
O1 H14C 3.5992 no . 2_665
O1 H21 2.8250 no . 2_766
N2 H12B 3.5744 no . 2_655
N2 H20 3.4808 no . 2_766
N2 H24 3.5400 no . 2_765
N3 H8 3.5014 no . 2_655
N3 H12A 3.3476 no . 2_655
N3 H12B 3.0684 no . 2_655
N3 H15A 3.2040 no . 2_665
N3 H20 3.2450 no . 2_766
N5 H20 3.3592 no . 2_766
C1 H24 3.3127 no . 2_765
C4 H15A 3.1764 no . 2_665
C4 H20 3.1516 no . 2_766
C4 H21 3.4660 no . 2_766
C6 H12B 3.2652 no . 2_655
C6 H24 3.4383 no . 2_765
C7 H12A 3.5987 no . 2_755
C7 H12B 3.5598 no . 2_655
C8 H12A 3.3787 no . 2_755
C8 H12C 3.1867 no . 2_755
C8 H15B 3.2855 no . 2_655
C8 H20 3.3340 no . 1_444
C9 H17A 3.3175 no . 2_765
C9 H20 3.1101 no . 1_444
C10 H14C 3.5586 no . 2_654
C10 H17A 2.9615 no . 2_765
C10 H20 3.2244 no . 1_444
C11 H12B 3.5823 no . 2_655
C11 H17A 3.4915 no . 2_765
C11 H24 3.0631 no . 2_765
C12 H8 3.4466 no . 2_755
C12 H19 3.1107 no . 2_766
C12 H20 3.2190 no . 2_766
C13 H15B 3.5713 no . 2_655
C13 H17B 3.1450 no . 1_544
C13 H21 3.2590 no . 1_444
C13 H21 3.3579 no . 2_755
C13 H22 3.2270 no . 2_755
C14 H10 3.5166 no . 2_654
C14 H13B 3.5071 no . 2_654
C14 H15A 3.2754 no . 2_665
C14 H24 2.9513 no . 2_765
C15 H8 3.5355 no . 2_655
C15 H14A 3.3492 no . 2_665
C15 H14B 3.2915 no . 2_665
C15 H15A 3.2422 no . 2_665
C15 H21 3.2102 no . 2_766
C16 H14B 3.2023 no . 2_665
C17 H13A 3.2535 no . 1_566
C17 H14B 3.5610 no . 2_665
C17 H17A 3.3973 no . 2_776
C17 H17B 3.1252 no . 2_776
C17 H19 3.4382 no . 2_776
C18 H13A 3.0888 no . 1_566
C18 H14C 3.3824 no . 2_765
C19 H12B 3.3127 no . 2_766
C19 H12C 3.3907 no . 2_766
C19 H13A 2.9629 no . 1_566
C20 H10 3.5111 no . 1_666
C20 H12B 3.2275 no . 2_766
C20 H12C 3.4368 no . 2_766
C20 H13B 3.5869 no . 1_666
C20 H22 3.3928 no . 2_766
C21 H13B 3.2024 no . 1_666
C21 H13C 3.2380 no . 1_666
C21 H13C 3.5640 no . 2_755
C21 H22 3.5550 no . 2_766
C22 H13A 3.5204 no . 2_755
C22 H13C 3.4157 no . 2_755
C22 H14A 3.5587 no . 2_765
C22 H14C 3.2867 no . 2_765
C22 H21 3.5571 no . 2_766
C23 H14A 3.3415 no . 2_765
C23 H14C 3.1159 no . 2_765
C23 H21 3.3458 no . 2_766
C24 H14A 3.2207 no . 2_765
C24 H14C 3.5879 no . 2_765
H8 Se1 2.9175 no . 2_755
H8 N3 3.5014 no . 2_655
H8 C12 3.4466 no . 2_755
H8 C15 3.5355 no . 2_655
H8 H12A 3.3777 no . 2_755
H8 H12C 2.7870 no . 2_755
H8 H15B 2.6771 no . 2_655
H10 C14 3.5166 no . 2_654
H10 C20 3.5111 no . 1_444
H10 H10 2.9138 no . 2_654
H10 H14B 3.5859 no . 2_654
H10 H14C 2.7057 no . 2_654
H10 H17A 2.8980 no . 2_765
H10 H17B 3.5411 no . 1_544
H10 H20 3.5624 no . 1_444
H12A N3 3.3476 no . 2_655
H12A C7 3.5987 no . 2_755
H12A C8 3.3787 no . 2_755
H12A H8 3.3777 no . 2_755
H12A H16 3.0120 no . 1_545
H12A H19 3.1490 no . 2_766
H12B N2 3.5744 no . 2_655
H12B N3 3.0684 no . 2_655
H12B C6 3.2652 no . 2_655
H12B C7 3.5598 no . 2_655
H12B C11 3.5823 no . 2_655
H12B C19 3.3127 no . 2_766
H12B C20 3.2275 no . 2_766
H12B H12B 3.4787 no . 2_655
H12B H14B 3.5164 no . 2_655
H12B H19 2.7511 no . 2_766
H12B H20 2.5641 no . 2_766
H12C C8 3.1867 no . 2_755
H12C C19 3.3907 no . 2_766
H12C C20 3.4368 no . 2_766
H12C H8 2.7870 no . 2_755
H12C H13A 3.1993 no . 2_755
H12C H19 2.9160 no . 2_766
H12C H20 2.9983 no . 2_766
H13A O1 3.3919 no . 1_544
H13A C17 3.2535 no . 1_544
H13A C18 3.0888 no . 1_544
H13A C19 2.9629 no . 1_544
H13A C22 3.5204 no . 2_755
H13A H12C 3.1993 no . 2_755
H13A H17A 3.3204 no . 2_765
H13A H17B 2.6284 no . 1_544
H13A H19 2.8281 no . 1_544
H13A H21 3.1333 no . 2_755
H13A H22 2.8204 no . 2_755
H13B O1 2.9738 no . 1_544
H13B C14 3.5071 no . 2_654
H13B C20 3.5869 no . 1_444
H13B C21 3.2024 no . 1_444
H13B H14B 3.3930 no . 2_654
H13B H14C 2.8258 no . 2_654
H13B H17B 2.8344 no . 1_544
H13B H21 3.1040 no . 1_444
H13B H21 3.3523 no . 2_755
H13C C21 3.2380 no . 1_444
H13C C21 3.5640 no . 2_755
H13C C22 3.4157 no . 2_755
H13C H13C 3.5613 no . 2_644
H13C H15B 2.7186 no . 2_655
H13C H20 3.5386 no . 1_444
H13C H21 2.7158 no . 1_444
H13C H21 3.0326 no . 2_755
H13C H22 2.7391 no . 2_755
H14A Se1 3.0616 no . 2_765
H14A O1 3.4520 no . 2_665
H14A C15 3.3492 no . 2_665
H14A C22 3.5587 no . 2_765
H14A C23 3.3415 no . 2_765
H14A C24 3.2207 no . 2_765
H14A H15A 2.8034 no . 2_665
H14A H15B 3.3347 no . 2_665
H14A H22 3.5489 no . 2_765
H14A H24 2.4187 no . 2_765
H14B O1 2.8268 no . 2_665
H14B C15 3.2915 no . 2_665
H14B C16 3.2023 no . 2_665
H14B C17 3.5610 no . 2_665
H14B H10 3.5859 no . 2_654
H14B H12B 3.5164 no . 2_655
H14B H13B 3.3930 no . 2_654
H14B H15A 2.8647 no . 2_665
H14B H16 2.9157 no . 2_665
H14B H17B 3.0785 no . 2_665
H14B H19 3.1555 no . 1_444
H14C O1 3.5992 no . 2_665
H14C C10 3.5586 no . 2_654
H14C C18 3.3824 no . 2_765
H14C C22 3.2867 no . 2_765
H14C C23 3.1159 no . 2_765
H14C C24 3.5879 no . 2_765
H14C H10 2.7057 no . 2_654
H14C H13B 2.8258 no . 2_654
H14C H24 3.0285 no . 2_765
H15A Se1 3.2727 no . 1_455
H15A N3 3.2040 no . 2_665
H15A C4 3.1764 no . 2_665
H15A C14 3.2754 no . 2_665
H15A C15 3.2422 no . 2_665
H15A H14A 2.8034 no . 2_665
H15A H14B 2.8647 no . 2_665
H15A H15A 2.5039 no . 2_665
H15A H16 3.5849 no . 2_665
H15B Se1 3.0526 no . 1_455
H15B C8 3.2855 no . 2_655
H15B C13 3.5713 no . 2_655
H15B H8 2.6771 no . 2_655
H15B H13C 2.7186 no . 2_655
H15B H14A 3.3347 no . 2_665
H15B H20 3.5010 no . 2_766
H15B H21 2.9431 no . 2_766
H16 Se1 3.2400 no . 2_765
H16 H12A 3.0120 no . 1_565
H16 H14B 2.9157 no . 2_665
H16 H15A 3.5849 no . 2_665
H17A C9 3.3175 no . 2_765
H17A C10 2.9615 no . 2_765
H17A C11 3.4915 no . 2_765
H17A C17 3.3973 no . 2_776
H17A H10 2.8980 no . 2_765
H17A H13A 3.3204 no . 2_765
H17A H17A 3.3957 no . 2_776
H17A H17B 2.6748 no . 2_776
H17A H19 3.0195 no . 2_776
H17B C13 3.1450 no . 1_566
H17B C17 3.1252 no . 2_776
H17B H10 3.5411 no . 1_566
H17B H13A 2.6284 no . 1_566
H17B H13B 2.8344 no . 1_566
H17B H14B 3.0785 no . 2_665
H17B H17A 2.6748 no . 2_776
H17B H17B 2.8251 no . 2_776
H17B H19 3.0376 no . 2_776
H19 C12 3.1107 no . 2_766
H19 C17 3.4382 no . 2_776
H19 H12A 3.1490 no . 2_766
H19 H12B 2.7511 no . 2_766
H19 H12C 2.9160 no . 2_766
H19 H13A 2.8281 no . 1_566
H19 H14B 3.1555 no . 1_666
H19 H17A 3.0195 no . 2_776
H19 H17B 3.0376 no . 2_776
H20 N2 3.4808 no . 2_766
H20 N3 3.2450 no . 2_766
H20 N5 3.3592 no . 2_766
H20 C4 3.1516 no . 2_766
H20 C8 3.3340 no . 1_666
H20 C9 3.1101 no . 1_666
H20 C10 3.2244 no . 1_666
H20 C12 3.2190 no . 2_766
H20 H10 3.5624 no . 1_666
H20 H12B 2.5641 no . 2_766
H20 H12C 2.9983 no . 2_766
H20 H13C 3.5386 no . 1_666
H20 H15B 3.5010 no . 2_766
H21 O1 2.8250 no . 2_766
H21 C4 3.4660 no . 2_766
H21 C13 3.2590 no . 1_666
H21 C13 3.3579 no . 2_755
H21 C15 3.2102 no . 2_766
H21 C22 3.5571 no . 2_766
H21 C23 3.3458 no . 2_766
H21 H13A 3.1333 no . 2_755
H21 H13B 3.1040 no . 1_666
H21 H13B 3.3523 no . 2_755
H21 H13C 2.7158 no . 1_666
H21 H13C 3.0326 no . 2_755
H21 H15B 2.9431 no . 2_766
H22 C13 3.2270 no . 2_755
H22 C20 3.3928 no . 2_766
H22 C21 3.5550 no . 2_766
H22 H13A 2.8204 no . 2_755
H22 H13C 2.7391 no . 2_755
H22 H14A 3.5489 no . 2_765
H24 Se1 2.9449 no . 2_765
H24 N2 3.5400 no . 2_765
H24 C1 3.3127 no . 2_765
H24 C6 3.4383 no . 2_765
H24 C11 3.0631 no . 2_765
H24 C14 2.9513 no . 2_765
H24 H14A 2.4187 no . 2_765
H24 H14C 3.0285 no . 2_765

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_chemical_name_systematic        '[Se(Tr4)]'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone, hexane'
####################################################################### 
# 
# 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_[Se(Tr5)]
_database_code_depnum_ccdc_archive 'CCDC 1024818'
_audit_update_record             
;
2014-09-17 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C30 H35 N3 O Se Si'
_chemical_formula_moiety         'C30 H35 N3 O Se Si'
_chemical_formula_weight         560.67
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,1/2-Y,1/2+Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,-Z
7 -X,1/2+Y,1/2-Z
8 1/2+X,+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   13.2692(12)
_cell_length_b                   19.8926(16)
_cell_length_c                   20.9790(19)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     5537.6(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14333
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      25.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2336.00
_exptl_absorpt_coefficient_mu    1.427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_T_max  0.867

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 11.628
_diffrn_reflns_number            64470
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_theta_max         25.353
_diffrn_reflns_theta_min         1.941
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             5063
_reflns_number_gt                4355
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0616
_refine_ls_wR_factor_gt          0.0584
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5063
_refine_ls_number_parameters     330
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0272P)²+2.7260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.003
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Si Si 0.0817 0.0704
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.08327(2) 0.37743(2) 0.53101(2) 0.02737(6) Uani 1 8 d . . .
Si1 Si 0.18716(4) 0.67992(2) 0.64728(2) 0.02597(11) Uani 1 8 d . . .
O1 O 0.10404(8) 0.61748(5) 0.64576(5) 0.0230(2) Uani 1 8 d . . .
N2 N -0.07816(10) 0.35430(7) 0.62055(7) 0.0244(3) Uani 1 8 d . . .
N3 N -0.13948(11) 0.38694(7) 0.66514(7) 0.0270(3) Uani 1 8 d . . .
N5 N -0.02924(10) 0.45644(7) 0.62112(6) 0.0203(3) Uani 1 8 d . . .
C1 C -0.01027(12) 0.39629(8) 0.59216(8) 0.0216(3) Uani 1 8 d . . .
C4 C -0.10590(12) 0.44794(9) 0.66353(8) 0.0228(4) Uani 1 8 d . . .
C6 C -0.10663(14) 0.28738(9) 0.60297(8) 0.0268(4) Uani 1 8 d . . .
C7 C -0.20833(14) 0.27203(10) 0.60232(9) 0.0342(4) Uani 1 8 d . . .
C8 C -0.23840(17) 0.20812(10) 0.58436(11) 0.0434(5) Uani 1 8 d . . .
C9 C -0.16849(18) 0.16057(11) 0.56753(11) 0.0471(5) Uani 1 8 d . . .
C10 C -0.06739(18) 0.17616(10) 0.56927(11) 0.0481(6) Uani 1 8 d . . .
C11 C -0.03545(16) 0.23970(9) 0.58756(10) 0.0376(5) Uani 1 8 d . . .
C12 C -0.13327(13) 0.51210(9) 0.69507(9) 0.0281(4) Uani 1 8 d . . .
C13 C -0.08648(13) 0.56316(9) 0.64830(9) 0.0271(4) Uani 1 8 d . . .
C14 C 0.00191(12) 0.52758(8) 0.61343(8) 0.0205(3) Uani 1 8 d . . .
C15 C 0.10859(12) 0.54584(8) 0.64127(8) 0.0203(3) Uani 1 8 d . . .
C16 C 0.11634(12) 0.51419(8) 0.70755(8) 0.0208(3) Uani 1 8 d . . .
C17 C 0.13385(12) 0.44507(8) 0.71410(8) 0.0237(4) Uani 1 8 d . . .
C18 C 0.12854(13) 0.41463(9) 0.77326(8) 0.0281(4) Uani 1 8 d . . .
C19 C 0.10471(13) 0.45169(10) 0.82681(9) 0.0311(4) Uani 1 8 d . . .
C20 C 0.08844(13) 0.52009(10) 0.82126(8) 0.0302(4) Uani 1 8 d . . .
C21 C 0.09442(13) 0.55110(9) 0.76186(8) 0.0250(4) Uani 1 8 d . . .
C22 C 0.19426(12) 0.52771(8) 0.59525(8) 0.0215(3) Uani 1 8 d . . .
C23 C 0.28546(13) 0.50108(9) 0.61540(8) 0.0278(4) Uani 1 8 d . . .
C24 C 0.36325(14) 0.48975(10) 0.57250(9) 0.0345(4) Uani 1 8 d . . .
C25 C 0.35186(14) 0.50604(10) 0.50912(9) 0.0335(4) Uani 1 8 d . . .
C26 C 0.26227(14) 0.53368(10) 0.48843(9) 0.0320(4) Uani 1 8 d . . .
C27 C 0.18452(13) 0.54443(9) 0.53089(8) 0.0276(4) Uani 1 8 d . . .
C28 C 0.25021(17) 0.69389(11) 0.56946(10) 0.0439(5) Uani 1 8 d . . .
C29 C 0.28515(16) 0.66535(11) 0.70925(11) 0.0471(5) Uani 1 8 d . . .
C30 C 0.10605(15) 0.75493(9) 0.66682(9) 0.0331(4) Uani 1 8 d . . .
C31 C 0.0306(2) 0.76693(12) 0.61310(12) 0.0580(7) Uani 1 8 d . . .
C32 C 0.04933(19) 0.74401(11) 0.72948(11) 0.0483(6) Uani 1 8 d . . .
C33 C 0.1725(2) 0.81777(11) 0.67412(12) 0.0546(6) Uani 1 8 d . . .
H7 H -0.25686 0.3049 0.61403 0.0410 Uiso 1 8 calc R . .
H8 H -0.30806 0.19712 0.5837 0.0521 Uiso 1 8 calc R . .
H9 H -0.18972 0.11702 0.5547 0.0565 Uiso 1 8 calc R . .
H10 H -0.01905 0.14307 0.55783 0.0577 Uiso 1 8 calc R . .
H11 H 0.03436 0.25013 0.58944 0.0451 Uiso 1 8 calc R . .
H12A H -0.10299 0.51567 0.73807 0.0337 Uiso 1 8 calc R . .
H12B H -0.20725 0.51763 0.69828 0.0337 Uiso 1 8 calc R . .
H13A H -0.06139 0.60295 0.67179 0.0326 Uiso 1 8 calc R . .
H13B H -0.13764 0.57829 0.61708 0.0326 Uiso 1 8 calc R . .
H14 H -0.00003 0.53967 0.56718 0.0246 Uiso 1 8 calc R . .
H17 H 0.14951 0.41887 0.67756 0.0285 Uiso 1 8 calc R . .
H18 H 0.14139 0.36782 0.77708 0.0338 Uiso 1 8 calc R . .
H19 H 0.09952 0.43035 0.86719 0.0373 Uiso 1 8 calc R . .
H20 H 0.07316 0.546 0.85805 0.0363 Uiso 1 8 calc R . .
H21 H 0.08334 0.59815 0.75851 0.0300 Uiso 1 8 calc R . .
H23 H 0.2948 0.49044 0.65915 0.0334 Uiso 1 8 calc R . .
H24 H 0.42475 0.47065 0.58696 0.0414 Uiso 1 8 calc R . .
H25 H 0.40526 0.4983 0.47986 0.0402 Uiso 1 8 calc R . .
H26 H 0.2541 0.54535 0.44483 0.0384 Uiso 1 8 calc R . .
H27 H 0.12324 0.56356 0.51607 0.0331 Uiso 1 8 calc R . .
H28A H 0.30146 0.65913 0.56277 0.0527 Uiso 1 8 calc R . .
H28B H 0.28233 0.73826 0.56933 0.0527 Uiso 1 8 calc R . .
H28C H 0.20016 0.69167 0.53518 0.0527 Uiso 1 8 calc R . .
H29A H 0.25314 0.6629 0.75128 0.0565 Uiso 1 8 calc R . .
H29B H 0.3337 0.70246 0.70868 0.0565 Uiso 1 8 calc R . .
H29C H 0.32021 0.623 0.70041 0.0565 Uiso 1 8 calc R . .
H31A H -0.01042 0.72649 0.60694 0.0696 Uiso 1 8 calc R . .
H31B H 0.06699 0.7772 0.57363 0.0696 Uiso 1 8 calc R . .
H31C H -0.01321 0.80482 0.62423 0.0696 Uiso 1 8 calc R . .
H32A H 0.01162 0.78479 0.74034 0.0580 Uiso 1 8 calc R . .
H32B H 0.09761 0.73395 0.76352 0.0580 Uiso 1 8 calc R . .
H32C H 0.00243 0.70628 0.72471 0.0580 Uiso 1 8 calc R . .
H33A H 0.20794 0.82649 0.63397 0.0655 Uiso 1 8 calc R . .
H33B H 0.22183 0.81036 0.70819 0.0655 Uiso 1 8 calc R . .
H33C H 0.13019 0.85651 0.68487 0.0655 Uiso 1 8 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Se1 C1 1.8240(17) yes . .
Si1 O1 1.6614(11) yes . .
Si1 C28 1.855(2) yes . .
Si1 C29 1.861(2) yes . .
Si1 C30 1.8849(19) yes . .
O1 C15 1.4295(19) yes . .
N2 N3 1.400(2) yes . .
N2 C1 1.365(2) yes . .
N2 C6 1.432(2) yes . .
N3 C4 1.293(2) yes . .
N5 C1 1.365(2) yes . .
N5 C4 1.362(2) yes . .
N5 C14 1.483(2) yes . .
C4 C12 1.483(3) yes . .
C6 C7 1.384(3) yes . .
C6 C11 1.377(3) yes . .
C7 C8 1.385(3) yes . .
C8 C9 1.371(3) yes . .
C9 C10 1.377(3) yes . .
C10 C11 1.387(3) yes . .
C12 C13 1.543(3) yes . .
C13 C14 1.553(2) yes . .
C14 C15 1.574(2) yes . .
C15 C16 1.530(2) yes . .
C15 C22 1.534(2) yes . .
C16 C17 1.401(2) yes . .
C16 C21 1.386(2) yes . .
C17 C18 1.383(2) yes . .
C18 C19 1.380(3) yes . .
C19 C20 1.383(3) yes . .
C20 C21 1.393(2) yes . .
C22 C23 1.387(2) yes . .
C22 C27 1.397(2) yes . .
C23 C24 1.388(3) yes . .
C24 C25 1.377(3) yes . .
C25 C26 1.380(3) yes . .
C26 C27 1.380(3) yes . .
C30 C31 1.526(3) yes . .
C30 C32 1.530(3) yes . .
C30 C33 1.538(3) yes . .
C7 H7 0.950 no . .
C8 H8 0.950 no . .
C9 H9 0.950 no . .
C10 H10 0.950 no . .
C11 H11 0.950 no . .
C12 H12A 0.990 no . .
C12 H12B 0.990 no . .
C13 H13A 0.990 no . .
C13 H13B 0.990 no . .
C14 H14 1.000 no . .
C17 H17 0.950 no . .
C18 H18 0.950 no . .
C19 H19 0.950 no . .
C20 H20 0.950 no . .
C21 H21 0.950 no . .
C23 H23 0.950 no . .
C24 H24 0.950 no . .
C25 H25 0.950 no . .
C26 H26 0.950 no . .
C27 H27 0.950 no . .
C28 H28A 0.980 no . .
C28 H28B 0.980 no . .
C28 H28C 0.980 no . .
C29 H29A 0.980 no . .
C29 H29B 0.980 no . .
C29 H29C 0.980 no . .
C31 H31A 0.980 no . .
C31 H31B 0.980 no . .
C31 H31C 0.980 no . .
C32 H32A 0.980 no . .
C32 H32B 0.980 no . .
C32 H32C 0.980 no . .
C33 H33A 0.980 no . .
C33 H33B 0.980 no . .
C33 H33C 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O1 Si1 C28 113.23(8) yes . . .
O1 Si1 C29 111.14(8) yes . . .
O1 Si1 C30 102.53(7) yes . . .
C28 Si1 C29 108.84(10) yes . . .
C28 Si1 C30 109.28(9) yes . . .
C29 Si1 C30 111.73(9) yes . . .
Si1 O1 C15 135.93(10) yes . . .
N3 N2 C1 113.04(13) yes . . .
N3 N2 C6 116.75(13) yes . . .
C1 N2 C6 129.08(14) yes . . .
N2 N3 C4 102.57(13) yes . . .
C1 N5 C4 108.64(14) yes . . .
C1 N5 C14 137.43(13) yes . . .
C4 N5 C14 113.43(13) yes . . .
Se1 C1 N2 129.05(12) yes . . .
Se1 C1 N5 128.22(12) yes . . .
N2 C1 N5 102.73(13) yes . . .
N3 C4 N5 113.01(15) yes . . .
N3 C4 C12 135.37(16) yes . . .
N5 C4 C12 111.57(15) yes . . .
N2 C6 C7 117.71(16) yes . . .
N2 C6 C11 121.32(16) yes . . .
C7 C6 C11 120.97(17) yes . . .
C6 C7 C8 119.10(18) yes . . .
C7 C8 C9 120.6(2) yes . . .
C8 C9 C10 119.8(2) yes . . .
C9 C10 C11 120.7(2) yes . . .
C6 C11 C10 118.88(19) yes . . .
C4 C12 C13 100.62(14) yes . . .
C12 C13 C14 107.67(14) yes . . .
N5 C14 C13 99.97(12) yes . . .
N5 C14 C15 115.50(13) yes . . .
C13 C14 C15 113.53(13) yes . . .
O1 C15 C14 102.51(12) yes . . .
O1 C15 C16 110.68(13) yes . . .
O1 C15 C22 107.88(12) yes . . .
C14 C15 C16 107.62(13) yes . . .
C14 C15 C22 112.25(13) yes . . .
C16 C15 C22 115.17(13) yes . . .
C15 C16 C17 120.27(14) yes . . .
C15 C16 C21 120.99(14) yes . . .
C17 C16 C21 118.29(15) yes . . .
C16 C17 C18 120.62(15) yes . . .
C17 C18 C19 120.55(17) yes . . .
C18 C19 C20 119.53(17) yes . . .
C19 C20 C21 120.16(17) yes . . .
C16 C21 C20 120.85(17) yes . . .
C15 C22 C23 122.98(15) yes . . .
C15 C22 C27 118.93(14) yes . . .
C23 C22 C27 117.80(15) yes . . .
C22 C23 C24 120.88(16) yes . . .
C23 C24 C25 120.42(17) yes . . .
C24 C25 C26 119.48(17) yes . . .
C25 C26 C27 120.19(17) yes . . .
C22 C27 C26 121.20(16) yes . . .
Si1 C30 C31 109.74(14) yes . . .
Si1 C30 C32 110.81(13) yes . . .
Si1 C30 C33 109.73(15) yes . . .
C31 C30 C32 109.51(18) yes . . .
C31 C30 C33 108.83(17) yes . . .
C32 C30 C33 108.18(17) yes . . .
C6 C7 H7 120.440 no . . .
C8 C7 H7 120.461 no . . .
C7 C8 H8 119.723 no . . .
C9 C8 H8 119.712 no . . .
C8 C9 H9 120.099 no . . .
C10 C9 H9 120.112 no . . .
C9 C10 H10 119.667 no . . .
C11 C10 H10 119.667 no . . .
C6 C11 H11 120.569 no . . .
C10 C11 H11 120.552 no . . .
C4 C12 H12A 111.649 no . . .
C4 C12 H12B 111.643 no . . .
C13 C12 H12A 111.651 no . . .
C13 C12 H12B 111.662 no . . .
H12A C12 H12B 109.416 no . . .
C12 C13 H13A 110.190 no . . .
C12 C13 H13B 110.177 no . . .
C14 C13 H13A 110.174 no . . .
C14 C13 H13B 110.166 no . . .
H13A C13 H13B 108.468 no . . .
N5 C14 H14 109.139 no . . .
C13 C14 H14 109.148 no . . .
C15 C14 H14 109.131 no . . .
C16 C17 H17 119.702 no . . .
C18 C17 H17 119.681 no . . .
C17 C18 H18 119.722 no . . .
C19 C18 H18 119.730 no . . .
C18 C19 H19 120.241 no . . .
C20 C19 H19 120.233 no . . .
C19 C20 H20 119.924 no . . .
C21 C20 H20 119.920 no . . .
C16 C21 H21 119.568 no . . .
C20 C21 H21 119.586 no . . .
C22 C23 H23 119.561 no . . .
C24 C23 H23 119.556 no . . .
C23 C24 H24 119.788 no . . .
C25 C24 H24 119.791 no . . .
C24 C25 H25 120.261 no . . .
C26 C25 H25 120.258 no . . .
C25 C26 H26 119.909 no . . .
C27 C26 H26 119.899 no . . .
C22 C27 H27 119.405 no . . .
C26 C27 H27 119.392 no . . .
Si1 C28 H28A 109.466 no . . .
Si1 C28 H28B 109.475 no . . .
Si1 C28 H28C 109.477 no . . .
H28A C28 H28B 109.466 no . . .
H28A C28 H28C 109.476 no . . .
H28B C28 H28C 109.466 no . . .
Si1 C29 H29A 109.477 no . . .
Si1 C29 H29B 109.477 no . . .
Si1 C29 H29C 109.467 no . . .
H29A C29 H29B 109.477 no . . .
H29A C29 H29C 109.467 no . . .
H29B C29 H29C 109.464 no . . .
C30 C31 H31A 109.473 no . . .
C30 C31 H31B 109.468 no . . .
C30 C31 H31C 109.478 no . . .
H31A C31 H31B 109.475 no . . .
H31A C31 H31C 109.470 no . . .
H31B C31 H31C 109.463 no . . .
C30 C32 H32A 109.471 no . . .
C30 C32 H32B 109.478 no . . .
C30 C32 H32C 109.469 no . . .
H32A C32 H32B 109.476 no . . .
H32A C32 H32C 109.477 no . . .
H32B C32 H32C 109.457 no . . .
C30 C33 H33A 109.473 no . . .
C30 C33 H33B 109.469 no . . .
C30 C33 H33C 109.471 no . . .
H33A C33 H33B 109.477 no . . .
H33A C33 H33C 109.480 no . . .
H33B C33 H33C 109.457 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C28 Si1 O1 C15 70.71(13) no . . . .
C29 Si1 O1 C15 -52.16(13) no . . . .
O1 Si1 C30 C31 -63.78(11) no . . . .
O1 Si1 C30 C32 57.28(12) no . . . .
O1 Si1 C30 C33 176.68(9) no . . . .
C30 Si1 O1 C15 -171.67(11) no . . . .
C28 Si1 C30 C31 56.61(13) no . . . .
C28 Si1 C30 C32 177.67(11) no . . . .
C28 Si1 C30 C33 -62.93(13) no . . . .
C29 Si1 C30 C31 177.12(10) no . . . .
C29 Si1 C30 C32 -61.82(14) no . . . .
C29 Si1 C30 C33 57.58(13) no . . . .
Si1 O1 C15 C14 -156.19(9) no . . . .
Si1 O1 C15 C16 89.28(15) no . . . .
Si1 O1 C15 C22 -37.56(18) no . . . .
N3 N2 C1 Se1 -179.12(12) no . . . .
N3 N2 C1 N5 1.12(17) no . . . .
C1 N2 N3 C4 -1.12(16) no . . . .
N3 N2 C6 C7 32.4(2) no . . . .
N3 N2 C6 C11 -147.21(13) no . . . .
C6 N2 N3 C4 -170.07(12) no . . . .
C1 N2 C6 C7 -134.43(16) no . . . .
C1 N2 C6 C11 45.9(2) no . . . .
C6 N2 C1 Se1 -11.9(3) no . . . .
C6 N2 C1 N5 168.38(14) no . . . .
N2 N3 C4 N5 0.64(17) no . . . .
N2 N3 C4 C12 177.75(16) no . . . .
C1 N5 C4 N3 0.02(18) no . . . .
C1 N5 C4 C12 -177.80(12) no . . . .
C4 N5 C1 Se1 179.56(13) no . . . .
C4 N5 C1 N2 -0.68(16) no . . . .
C1 N5 C14 C13 158.69(16) no . . . .
C1 N5 C14 C15 -79.1(2) no . . . .
C14 N5 C1 Se1 8.6(3) no . . . .
C14 N5 C1 N2 -171.62(15) no . . . .
C4 N5 C14 C13 -11.95(15) no . . . .
C4 N5 C14 C15 110.26(14) no . . . .
C14 N5 C4 N3 173.35(12) no . . . .
C14 N5 C4 C12 -4.47(17) no . . . .
N3 C4 C12 C13 -158.39(19) no . . . .
N5 C4 C12 C13 18.74(16) no . . . .
N2 C6 C7 C8 178.79(14) no . . . .
N2 C6 C11 C10 -178.34(14) no . . . .
C7 C6 C11 C10 2.0(3) no . . . .
C11 C6 C7 C8 -1.6(3) no . . . .
C6 C7 C8 C9 0.1(3) no . . . .
C7 C8 C9 C10 0.8(3) no . . . .
C8 C9 C10 C11 -0.4(3) no . . . .
C9 C10 C11 C6 -1.1(3) no . . . .
C4 C12 C13 C14 -25.76(16) no . . . .
C12 C13 C14 N5 23.26(16) no . . . .
C12 C13 C14 C15 -100.34(14) no . . . .
N5 C14 C15 O1 -162.23(12) no . . . .
N5 C14 C15 C16 -45.48(16) no . . . .
N5 C14 C15 C22 82.27(15) no . . . .
C13 C14 C15 O1 -47.58(16) no . . . .
C13 C14 C15 C16 69.17(15) no . . . .
C13 C14 C15 C22 -163.08(12) no . . . .
O1 C15 C16 C17 -172.33(11) no . . . .
O1 C15 C16 C21 15.47(19) no . . . .
O1 C15 C22 C23 106.77(15) no . . . .
O1 C15 C22 C27 -66.94(16) no . . . .
C14 C15 C16 C17 76.40(16) no . . . .
C14 C15 C16 C21 -95.80(15) no . . . .
C14 C15 C22 C23 -141.03(13) no . . . .
C14 C15 C22 C27 45.26(18) no . . . .
C16 C15 C22 C23 -17.4(2) no . . . .
C16 C15 C22 C27 168.88(12) no . . . .
C22 C15 C16 C17 -49.64(19) no . . . .
C22 C15 C16 C21 138.16(14) no . . . .
C15 C16 C17 C18 -171.92(12) no . . . .
C15 C16 C21 C20 171.39(13) no . . . .
C17 C16 C21 C20 -1.0(2) no . . . .
C21 C16 C17 C18 0.5(2) no . . . .
C16 C17 C18 C19 0.8(2) no . . . .
C17 C18 C19 C20 -1.6(2) no . . . .
C18 C19 C20 C21 1.1(2) no . . . .
C19 C20 C21 C16 0.2(3) no . . . .
C15 C22 C23 C24 -175.56(13) no . . . .
C15 C22 C27 C26 175.24(13) no . . . .
C23 C22 C27 C26 1.2(2) no . . . .
C27 C22 C23 C24 -1.8(2) no . . . .
C22 C23 C24 C25 1.3(3) no . . . .
C23 C24 C25 C26 -0.1(3) no . . . .
C24 C25 C26 C27 -0.5(3) no . . . .
C25 C26 C27 C22 -0.1(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Se1 C6 3.4406(18) no . .
Se1 C11 3.376(2) no . .
Se1 C22 3.5947(17) no . .
Se1 C27 3.5835(18) no . .
Si1 C22 3.2200(17) no . .
O1 C13 2.750(2) no . .
O1 C21 2.774(2) no . .
O1 C23 3.400(2) no . .
O1 C27 3.010(2) no . .
O1 C31 3.203(3) no . .
O1 C32 3.154(2) no . .
N2 C12 3.582(2) no . .
N3 C7 2.792(2) no . .
N3 C13 3.593(2) no . .
N3 C14 3.539(2) no . .
N5 C6 3.537(2) no . .
N5 C16 2.888(2) no . .
N5 C17 2.922(2) no . .
N5 C22 3.332(2) no . .
C1 C11 3.134(2) no . .
C1 C12 3.554(2) no . .
C1 C15 3.521(2) no . .
C1 C17 3.338(2) no . .
C4 C6 3.437(3) no . .
C4 C15 3.480(2) no . .
C4 C16 3.359(2) no . .
C4 C17 3.354(2) no . .
C6 C9 2.755(3) no . .
C7 C10 2.760(3) no . .
C8 C11 2.766(3) no . .
C12 C15 3.468(2) no . .
C12 C16 3.323(2) no . .
C12 C21 3.420(2) no . .
C13 C16 3.120(2) no . .
C13 C21 3.390(2) no . .
C14 C17 3.197(2) no . .
C14 C21 3.380(2) no . .
C14 C27 2.997(2) no . .
C16 C19 2.798(3) no . .
C16 C23 2.973(2) no . .
C17 C20 2.765(2) no . .
C17 C22 3.092(2) no . .
C17 C23 3.095(2) no . .
C18 C21 2.763(3) no . .
C21 C29 3.576(3) no . .
C22 C25 2.797(2) no . .
C22 C28 3.431(3) no . .
C23 C26 2.759(3) no . .
C24 C27 2.751(3) no . .
C27 C28 3.202(3) no . .
C28 C31 3.382(3) no . .
C28 C33 3.458(3) no . .
C29 C32 3.524(3) no . .
C29 C33 3.460(3) no . .
N3 C18 3.384(2) no . 8_456
C18 N3 3.384(2) no . 8_556
Se1 H11 2.8873 no . .
Se1 H14 3.4948 no . .
Se1 H17 3.3022 no . .
Si1 H21 3.1605 no . .
Si1 H31A 2.9065 no . .
Si1 H31B 2.9453 no . .
Si1 H32B 2.9179 no . .
Si1 H32C 2.9870 no . .
Si1 H33A 2.9419 no . .
Si1 H33B 2.9287 no . .
O1 H13A 2.2804 no . .
O1 H13B 3.3547 no . .
O1 H14 2.6496 no . .
O1 H21 2.4121 no . .
O1 H23 3.5878 no . .
O1 H27 2.9356 no . .
O1 H28A 3.2527 no . .
O1 H28C 3.0309 no . .
O1 H29A 3.1034 no . .
O1 H29C 3.0910 no . .
O1 H31A 2.7699 no . .
O1 H31B 3.5534 no . .
O1 H32B 3.3880 no . .
O1 H32C 2.7716 no . .
N2 H7 2.5704 no . .
N2 H11 2.6361 no . .
N2 H17 3.4938 no . .
N3 H7 2.4978 no . .
N3 H12A 3.0221 no . .
N3 H12B 2.8374 no . .
N5 H12A 2.8923 no . .
N5 H12B 3.1115 no . .
N5 H13A 3.1315 no . .
N5 H13B 2.8198 no . .
N5 H17 2.7543 no . .
C1 H11 2.9677 no . .
C1 H14 2.9031 no . .
C1 H17 2.8119 no . .
C4 H13A 3.1444 no . .
C4 H13B 2.8019 no . .
C4 H14 3.0641 no . .
C4 H17 3.4506 no . .
C6 H8 3.2452 no . .
C6 H10 3.2386 no . .
C7 H9 3.2507 no . .
C7 H11 3.2609 no . .
C8 H10 3.2335 no . .
C9 H7 3.2511 no . .
C9 H11 3.2604 no . .
C10 H8 3.2348 no . .
C11 H7 3.2591 no . .
C11 H9 3.2590 no . .
C12 H14 3.2596 no . .
C13 H21 3.3027 no . .
C13 H31A 3.5111 no . .
C13 H32C 3.4738 no . .
C14 H12A 2.9717 no . .
C14 H12B 3.3031 no . .
C14 H17 3.2129 no . .
C14 H21 3.5216 no . .
C14 H27 2.6974 no . .
C15 H12A 3.5166 no . .
C15 H13A 2.6054 no . .
C15 H13B 3.3689 no . .
C15 H17 2.6933 no . .
C15 H21 2.6916 no . .
C15 H23 2.7314 no . .
C15 H27 2.6572 no . .
C15 H29C 3.4322 no . .
C16 H12A 2.9801 no . .
C16 H13A 3.0401 no . .
C16 H14 3.3635 no . .
C16 H18 3.2735 no . .
C16 H20 3.2707 no . .
C16 H23 2.6195 no . .
C16 H29A 3.5900 no . .
C16 H29C 3.4678 no . .
C17 H12A 3.4787 no . .
C17 H19 3.2570 no . .
C17 H21 3.2543 no . .
C17 H23 2.5893 no . .
C18 H20 3.2455 no . .
C18 H23 3.5878 no . .
C19 H12A 3.5611 no . .
C19 H17 3.2532 no . .
C19 H21 3.2591 no . .
C20 H12A 3.0832 no . .
C20 H18 3.2447 no . .
C21 H12A 2.7582 no . .
C21 H13A 2.9848 no . .
C21 H17 3.2529 no . .
C21 H19 3.2645 no . .
C21 H29A 3.0710 no . .
C21 H29C 3.5615 no . .
C21 H32C 3.4098 no . .
C22 H14 2.6552 no . .
C22 H17 2.8323 no . .
C22 H24 3.2669 no . .
C22 H26 3.2729 no . .
C22 H28A 3.0532 no . .
C22 H28C 3.4975 no . .
C22 H29C 3.3546 no . .
C23 H17 2.7621 no . .
C23 H25 3.2581 no . .
C23 H27 3.2435 no . .
C23 H28A 3.3390 no . .
C23 H29C 3.0455 no . .
C24 H26 3.2396 no . .
C24 H28A 3.4737 no . .
C25 H23 3.2521 no . .
C25 H27 3.2455 no . .
C25 H28A 3.3149 no . .
C26 H24 3.2393 no . .
C26 H28A 2.9884 no . .
C26 H28C 3.3939 no . .
C27 H14 2.5662 no . .
C27 H23 3.2458 no . .
C27 H25 3.2508 no . .
C27 H28A 2.8392 no . .
C27 H28C 2.9377 no . .
C28 H27 3.2886 no . .
C28 H29B 3.1284 no . .
C28 H29C 3.2247 no . .
C28 H31B 2.9436 no . .
C28 H33A 3.0173 no . .
C29 H21 3.1664 no . .
C29 H28A 3.0831 no . .
C29 H28B 3.2744 no . .
C29 H32B 3.0580 no . .
C29 H33B 3.0046 no . .
C30 H28B 3.1248 no . .
C30 H28C 3.2817 no . .
C30 H29A 3.2094 no . .
C30 H29B 3.3144 no . .
C31 H28B 3.5108 no . .
C31 H28C 3.1584 no . .
C31 H32A 2.7047 no . .
C31 H32B 3.3435 no . .
C31 H32C 2.6604 no . .
C31 H33A 2.6707 no . .
C31 H33B 3.3414 no . .
C31 H33C 2.6812 no . .
C32 H13A 3.3907 no . .
C32 H21 2.9989 no . .
C32 H29A 3.1822 no . .
C32 H31A 2.7127 no . .
C32 H31B 3.3438 no . .
C32 H31C 2.6509 no . .
C32 H33A 3.3371 no . .
C32 H33B 2.6797 no . .
C32 H33C 2.6524 no . .
C33 H28B 3.0753 no . .
C33 H29B 3.2188 no . .
C33 H31A 3.3432 no . .
C33 H31B 2.6565 no . .
C33 H31C 2.6900 no . .
C33 H32A 2.6304 no . .
C33 H32B 2.6993 no . .
C33 H32C 3.3376 no . .
H7 H8 2.3374 no . .
H8 H9 2.3184 no . .
H9 H10 2.3241 no . .
H10 H11 2.3404 no . .
H12A H13A 2.2919 no . .
H12A H13B 2.8646 no . .
H12A H20 3.4875 no . .
H12A H21 2.9982 no . .
H12B H13A 2.6335 no . .
H12B H13B 2.2828 no . .
H13A H14 2.6578 no . .
H13A H21 2.6471 no . .
H13A H31A 2.8893 no . .
H13A H32C 2.4849 no . .
H13B H14 2.2406 no . .
H13B H31A 3.4038 no . .
H14 H27 2.0127 no . .
H17 H18 2.3242 no . .
H17 H23 2.4275 no . .
H18 H19 2.3302 no . .
H19 H20 2.3349 no . .
H20 H21 2.3356 no . .
H21 H29A 2.5997 no . .
H21 H29C 3.4072 no . .
H21 H32B 2.7101 no . .
H21 H32C 2.5064 no . .
H23 H24 2.3285 no . .
H23 H29C 2.7958 no . .
H24 H25 2.3276 no . .
H25 H26 2.3322 no . .
H26 H27 2.3195 no . .
H26 H28A 3.4117 no . .
H26 H28C 3.5464 no . .
H27 H28A 3.1885 no . .
H27 H28C 2.7744 no . .
H28A H29B 3.2087 no . .
H28A H29C 2.9860 no . .
H28B H29B 3.0852 no . .
H28B H31B 2.9619 no . .
H28B H33A 2.4277 no . .
H28B H33B 3.3448 no . .
H28C H31A 3.2487 no . .
H28C H31B 2.5822 no . .
H28C H33A 3.3910 no . .
H29A H32B 2.5145 no . .
H29A H32C 3.4817 no . .
H29A H33B 3.0975 no . .
H29B H32B 3.3956 no . .
H29B H33A 3.3658 no . .
H29B H33B 2.6097 no . .
H31A H32A 3.0435 no . .
H31A H32B 3.5871 no . .
H31A H32C 2.5090 no . .
H31A H33A 3.5601 no . .
H31A H33C 3.5838 no . .
H31B H32A 3.5769 no . .
H31B H32C 3.5735 no . .
H31B H33A 2.4621 no . .
H31B H33B 3.5532 no . .
H31B H33C 2.9391 no . .
H31C H32A 2.4901 no . .
H31C H32B 3.5621 no . .
H31C H32C 2.8860 no . .
H31C H33A 2.9730 no . .
H31C H33B 3.5835 no . .
H31C H33C 2.5093 no . .
H32A H33A 3.5290 no . .
H32A H33B 2.9144 no . .
H32A H33C 2.4218 no . .
H32B H33A 3.5943 no . .
H32B H33B 2.5248 no . .
H32B H33C 2.9755 no . .
H32C H33B 3.5892 no . .
H32C H33C 3.5360 no . .
Se1 H8 3.1733 no . 6_556
Se1 H9 3.5098 no . 6_556
Se1 H13B 3.3088 no . 5_566
Se1 H14 2.8606 no . 5_566
Se1 H27 3.1404 no . 5_566
Se1 H28B 3.3898 no . 2_545
N2 H26 3.3640 no . 5_566
N2 H27 3.3530 no . 5_566
N2 H32A 3.3479 no . 7_546
N2 H32B 3.4225 no . 7_546
N3 H18 3.1731 no . 8_456
N3 H26 3.0741 no . 5_566
N3 H32A 3.3075 no . 7_546
N3 H32B 3.4367 no . 7_546
N3 H33B 3.2522 no . 7_546
N3 H33C 3.2067 no . 7_546
N5 H26 3.2891 no . 5_566
N5 H27 3.1619 no . 5_566
C1 H14 3.5799 no . 5_566
C1 H26 3.5239 no . 5_566
C1 H27 2.8356 no . 5_566
C4 H26 3.0088 no . 5_566
C6 H28C 3.1802 no . 5_566
C6 H32A 3.5210 no . 7_546
C6 H32B 2.9982 no . 7_546
C7 H28C 2.9756 no . 5_566
C7 H32B 3.2640 no . 7_546
C8 H13B 3.1380 no . 2_445
C8 H28B 3.4458 no . 5_566
C8 H28C 3.2435 no . 5_566
C8 H29A 3.5689 no . 7_546
C8 H31A 3.3862 no . 2_445
C9 H13B 3.2214 no . 2_445
C9 H20 3.0384 no . 7_546
C9 H25 3.4545 no . 6_456
C9 H31B 3.4808 no . 5_566
C10 H20 3.0058 no . 7_546
C10 H28A 3.5475 no . 2_545
C10 H31B 3.1382 no . 5_566
C11 H28A 3.5326 no . 2_545
C11 H28B 3.3805 no . 2_545
C11 H31B 3.4239 no . 5_566
C11 H32B 3.2333 no . 7_546
C12 H23 3.2326 no . 8_456
C12 H26 3.5342 no . 5_566
C12 H29A 3.5408 no . 8_456
C12 H29C 3.1711 no . 8_456
C13 H8 3.3009 no . 2_455
C13 H29A 3.5922 no . 8_456
C16 H12B 3.0638 no . 8_556
C17 H12B 3.1477 no . 8_556
C17 H33A 3.5773 no . 2_545
C17 H33B 3.2960 no . 2_545
C18 H7 3.5592 no . 8_556
C18 H12B 3.0500 no . 8_556
C18 H31C 3.4261 no . 7_546
C18 H32A 3.1955 no . 7_546
C18 H33B 3.1793 no . 2_545
C19 H12B 2.8676 no . 8_556
C19 H24 3.0194 no . 8_456
C19 H25 3.3640 no . 4_565
C19 H26 3.1054 no . 4_565
C19 H31C 3.3264 no . 7_546
C20 H9 3.5065 no . 7_556
C20 H12B 2.7423 no . 8_556
C20 H24 3.0647 no . 8_456
C20 H25 3.3484 no . 4_565
C20 H26 3.5750 no . 4_565
C21 H12B 2.8405 no . 8_556
C23 H12A 3.4242 no . 8_556
C23 H33A 3.4959 no . 2_545
C23 H33C 3.4128 no . 2_545
C24 H9 3.4823 no . 6_556
C24 H19 3.5813 no . 8_556
C24 H20 3.3366 no . 8_556
C24 H25 3.2708 no . 5_666
C24 H33C 3.5482 no . 2_545
C25 H9 2.8442 no . 6_556
C25 H19 3.2990 no . 4_564
C25 H20 3.4794 no . 4_564
C25 H25 3.2323 no . 5_666
C26 H9 3.1955 no . 6_556
C26 H13B 3.5490 no . 5_566
C26 H19 3.2163 no . 4_564
C28 H11 3.0982 no . 2_555
C29 H12A 3.5057 no . 8_556
C29 H12B 3.5226 no . 8_556
C29 H13A 3.4519 no . 8_556
C29 H32C 3.3007 no . 8_556
C31 H8 3.3209 no . 2_455
C32 H18 3.5340 no . 7_556
C32 H29B 3.2485 no . 8_456
C33 H17 3.1026 no . 2_555
C33 H18 3.4283 no . 2_555
C33 H23 3.4763 no . 2_555
H7 C18 3.5592 no . 8_456
H7 H18 2.9339 no . 8_456
H7 H19 3.1646 no . 8_456
H7 H26 3.2249 no . 5_566
H7 H28C 3.2201 no . 5_566
H7 H31A 3.4628 no . 2_445
H7 H31C 3.0585 no . 2_445
H8 Se1 3.1733 no . 6_456
H8 C13 3.3009 no . 2_445
H8 C31 3.3209 no . 2_445
H8 H13A 3.1504 no . 2_445
H8 H13B 2.5685 no . 2_445
H8 H28B 3.4750 no . 5_566
H8 H31A 2.5260 no . 2_445
H8 H31C 3.3072 no . 2_445
H9 Se1 3.5098 no . 6_456
H9 C20 3.5065 no . 7_546
H9 C24 3.4823 no . 6_456
H9 C25 2.8442 no . 6_456
H9 C26 3.1955 no . 6_456
H9 H13B 2.7484 no . 2_445
H9 H20 2.7818 no . 7_546
H9 H25 2.7160 no . 6_456
H9 H26 3.3149 no . 6_456
H10 H20 2.7127 no . 7_546
H10 H25 3.0891 no . 6_456
H10 H28A 2.9067 no . 2_545
H10 H31B 3.2444 no . 5_566
H11 C28 3.0982 no . 2_545
H11 H28A 2.8872 no . 2_545
H11 H28B 2.4800 no . 2_545
H11 H29B 3.1972 no . 2_545
H11 H32B 3.5617 no . 7_546
H12A C23 3.4242 no . 8_456
H12A C29 3.5057 no . 8_456
H12A H23 2.5963 no . 8_456
H12A H29A 3.5032 no . 8_456
H12A H29C 2.6950 no . 8_456
H12A H33C 3.5732 no . 7_546
H12B C16 3.0638 no . 8_456
H12B C17 3.1477 no . 8_456
H12B C18 3.0500 no . 8_456
H12B C19 2.8676 no . 8_456
H12B C20 2.7423 no . 8_456
H12B C21 2.8405 no . 8_456
H12B C29 3.5226 no . 8_456
H12B H19 3.3875 no . 8_456
H12B H20 3.1946 no . 8_456
H12B H21 3.3329 no . 8_456
H12B H23 3.0396 no . 8_456
H12B H26 3.3121 no . 5_566
H12B H29A 3.1220 no . 8_456
H12B H29C 3.0073 no . 8_456
H13A C29 3.4519 no . 8_456
H13A H8 3.1504 no . 2_455
H13A H29A 3.1755 no . 8_456
H13A H29B 3.4849 no . 8_456
H13A H29C 3.1330 no . 8_456
H13B Se1 3.3088 no . 5_566
H13B C8 3.1380 no . 2_455
H13B C9 3.2214 no . 2_455
H13B C26 3.5490 no . 5_566
H13B H8 2.5685 no . 2_455
H13B H9 2.7484 no . 2_455
H13B H26 3.1819 no . 5_566
H13B H29A 3.5440 no . 8_456
H14 Se1 2.8606 no . 5_566
H14 C1 3.5799 no . 5_566
H14 H14 3.2305 no . 5_566
H14 H27 3.1528 no . 5_566
H17 C33 3.1026 no . 2_545
H17 H33A 2.7913 no . 2_545
H17 H33B 2.8261 no . 2_545
H17 H33C 3.1792 no . 2_545
H18 N3 3.1731 no . 8_556
H18 C32 3.5340 no . 7_546
H18 C33 3.4283 no . 2_545
H18 H7 2.9339 no . 8_556
H18 H31C 2.9581 no . 7_546
H18 H32A 2.6427 no . 7_546
H18 H33B 2.5864 no . 2_545
H19 C24 3.5813 no . 8_456
H19 C25 3.2990 no . 4_565
H19 C26 3.2163 no . 4_565
H19 H7 3.1646 no . 8_556
H19 H12B 3.3875 no . 8_556
H19 H24 2.6355 no . 8_456
H19 H25 2.7578 no . 4_565
H19 H26 2.5806 no . 4_565
H19 H31C 2.7531 no . 7_546
H19 H33C 3.5554 no . 7_546
H20 C9 3.0384 no . 7_556
H20 C10 3.0058 no . 7_556
H20 C24 3.3366 no . 8_456
H20 C25 3.4794 no . 4_565
H20 H9 2.7818 no . 7_556
H20 H10 2.7127 no . 7_556
H20 H12B 3.1946 no . 8_556
H20 H24 2.7305 no . 8_456
H20 H25 2.7183 no . 4_565
H20 H26 3.4453 no . 4_565
H21 H12B 3.3329 no . 8_556
H23 C12 3.2326 no . 8_556
H23 C33 3.4763 no . 2_545
H23 H12A 2.5963 no . 8_556
H23 H12B 3.0396 no . 8_556
H23 H33A 3.3041 no . 2_545
H23 H33C 2.8948 no . 2_545
H24 C19 3.0194 no . 8_556
H24 C20 3.0647 no . 8_556
H24 H19 2.6355 no . 8_556
H24 H20 2.7305 no . 8_556
H24 H25 2.7266 no . 5_666
H24 H31C 3.5876 no . 2_545
H24 H33A 3.5066 no . 2_545
H24 H33C 3.1474 no . 2_545
H25 C9 3.4545 no . 6_556
H25 C19 3.3640 no . 4_564
H25 C20 3.3484 no . 4_564
H25 C24 3.2708 no . 5_666
H25 C25 3.2323 no . 5_666
H25 H9 2.7160 no . 6_556
H25 H10 3.0891 no . 6_556
H25 H19 2.7578 no . 4_564
H25 H20 2.7183 no . 4_564
H25 H24 2.7266 no . 5_666
H25 H25 2.6533 no . 5_666
H26 N2 3.3640 no . 5_566
H26 N3 3.0741 no . 5_566
H26 N5 3.2891 no . 5_566
H26 C1 3.5239 no . 5_566
H26 C4 3.0088 no . 5_566
H26 C12 3.5342 no . 5_566
H26 C19 3.1054 no . 4_564
H26 C20 3.5750 no . 4_564
H26 H7 3.2249 no . 5_566
H26 H9 3.3149 no . 6_556
H26 H12B 3.3121 no . 5_566
H26 H13B 3.1819 no . 5_566
H26 H19 2.5806 no . 4_564
H26 H20 3.4453 no . 4_564
H27 Se1 3.1404 no . 5_566
H27 N2 3.3530 no . 5_566
H27 N5 3.1619 no . 5_566
H27 C1 2.8356 no . 5_566
H27 H14 3.1528 no . 5_566
H28A C10 3.5475 no . 2_555
H28A C11 3.5326 no . 2_555
H28A H10 2.9067 no . 2_555
H28A H11 2.8872 no . 2_555
H28B Se1 3.3898 no . 2_555
H28B C8 3.4458 no . 5_566
H28B C11 3.3805 no . 2_555
H28B H8 3.4750 no . 5_566
H28B H11 2.4800 no . 2_555
H28C C6 3.1802 no . 5_566
H28C C7 2.9756 no . 5_566
H28C C8 3.2435 no . 5_566
H28C H7 3.2201 no . 5_566
H29A C8 3.5689 no . 7_556
H29A C12 3.5408 no . 8_556
H29A C13 3.5922 no . 8_556
H29A H12A 3.5032 no . 8_556
H29A H12B 3.1220 no . 8_556
H29A H13A 3.1755 no . 8_556
H29A H13B 3.5440 no . 8_556
H29A H32C 3.4555 no . 8_556
H29B C32 3.2485 no . 8_556
H29B H11 3.1972 no . 2_555
H29B H13A 3.4849 no . 8_556
H29B H32A 3.0659 no . 8_556
H29B H32C 2.6403 no . 8_556
H29C C12 3.1711 no . 8_556
H29C H12A 2.6950 no . 8_556
H29C H12B 3.0073 no . 8_556
H29C H13A 3.1330 no . 8_556
H29C H32C 3.3254 no . 8_556
H31A C8 3.3862 no . 2_455
H31A H7 3.4628 no . 2_455
H31A H8 2.5260 no . 2_455
H31B C9 3.4808 no . 5_566
H31B C10 3.1382 no . 5_566
H31B C11 3.4239 no . 5_566
H31B H10 3.2444 no . 5_566
H31C C18 3.4261 no . 7_556
H31C C19 3.3264 no . 7_556
H31C H7 3.0585 no . 2_455
H31C H8 3.3072 no . 2_455
H31C H18 2.9581 no . 7_556
H31C H19 2.7531 no . 7_556
H31C H24 3.5876 no . 2_555
H32A N2 3.3479 no . 7_556
H32A N3 3.3075 no . 7_556
H32A C6 3.5210 no . 7_556
H32A C18 3.1955 no . 7_556
H32A H18 2.6427 no . 7_556
H32A H29B 3.0659 no . 8_456
H32B N2 3.4225 no . 7_556
H32B N3 3.4367 no . 7_556
H32B C6 2.9982 no . 7_556
H32B C7 3.2640 no . 7_556
H32B C11 3.2333 no . 7_556
H32B H11 3.5617 no . 7_556
H32C C29 3.3007 no . 8_456
H32C H29A 3.4555 no . 8_456
H32C H29B 2.6403 no . 8_456
H32C H29C 3.3254 no . 8_456
H33A C17 3.5773 no . 2_555
H33A C23 3.4959 no . 2_555
H33A H17 2.7913 no . 2_555
H33A H23 3.3041 no . 2_555
H33A H24 3.5066 no . 2_555
H33B N3 3.2522 no . 7_556
H33B C17 3.2960 no . 2_555
H33B C18 3.1793 no . 2_555
H33B H17 2.8261 no . 2_555
H33B H18 2.5864 no . 2_555
H33C N3 3.2067 no . 7_556
H33C C23 3.4128 no . 2_555
H33C C24 3.5482 no . 2_555
H33C H12A 3.5732 no . 7_556
H33C H17 3.1792 no . 2_555
H33C H19 3.5554 no . 7_556
H33C H23 2.8948 no . 2_555
H33C H24 3.1474 no . 2_555

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        '[Se(Tr5)]'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone, hexane'
