# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_xcalibur
_database_code_depnum_ccdc_archive 'CCDC 2061434'
loop_
_audit_author_name
_audit_author_address
'Youhei Takeda'
;Osaka University
Japan
;
_audit_update_record             
;
2021-02-19 deposited with the CCDC.	2021-08-20 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C44 H26 N4 Se2'
_chemical_formula_moiety         'C44 H26 N4 Se2'
_chemical_formula_weight         768.64
_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_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
#------------------------------------------------------------------------------
_cell_length_a                   8.0558(2)
_cell_length_b                   11.3915(3)
_cell_length_c                   37.9160(16)
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.548(3)
_cell_angle_gamma                90.0000
_cell_volume                     3468.51(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8094
_cell_measurement_theta_min      4.07
_cell_measurement_theta_max      74.62
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1544.00
_exptl_absorpt_coefficient_mu    2.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.465
_exptl_absorpt_correction_T_max  0.863

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

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            18324
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_theta_max         75.037
_diffrn_reflns_theta_min         4.053
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       47
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3501
_reflns_number_gt                3274
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1236
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3501
_refine_ls_number_parameters     227
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0736P)²+8.2703P] 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         1.06
_refine_diff_density_min         -0.86
_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 0.0181 0.0091
;
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 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.7943 1.1372
;
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_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.36135(4) 0.80922(2) 0.29668(2) 0.02675(14) Uani 1 1 d . . . . .
N1 N 0.5829(3) 0.74496(18) 0.36244(6) 0.0220(4) Uani 1 1 d . . . . .
N2 N 0.250000 0.5573(3) 0.500000 0.0212(6) Uani 1 2 d S T P . .
N3 N 0.250000 0.3084(3) 0.500000 0.0229(7) Uani 1 2 d S T P . .
C1 C 0.3224(3) 0.4959(2) 0.47527(7) 0.0208(5) Uani 1 1 d . . . . .
C2 C 0.3250(3) 0.3702(2) 0.47558(7) 0.0219(5) Uani 1 1 d . . . . .
C3 C 0.4102(3) 0.3106(2) 0.44892(7) 0.0237(6) Uani 1 1 d . . . . .
H3 H 0.415949 0.227325 0.449207 0.028 Uiso 1 1 calc R U . . .
C4 C 0.4822(3) 0.3706(2) 0.42344(7) 0.0228(5) Uani 1 1 d . . . . .
H4 H 0.539326 0.328398 0.406485 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4747(3) 0.4976(2) 0.42127(7) 0.0217(5) Uani 1 1 d . . . . .
C6 C 0.3970(3) 0.5588(2) 0.44768(7) 0.0213(5) Uani 1 1 d . . . . .
C7 C 0.5401(3) 0.5591(2) 0.39332(7) 0.0218(5) Uani 1 1 d . . . . .
H7 H 0.593080 0.516904 0.375731 0.026 Uiso 1 1 calc R U . . .
C8 C 0.5281(3) 0.6815(2) 0.39106(7) 0.0199(5) Uani 1 1 d . . . . .
C9 C 0.4538(3) 0.7416(2) 0.41841(7) 0.0229(5) Uani 1 1 d . . . . .
H9 H 0.447804 0.824832 0.417790 0.027 Uiso 1 1 calc R U . . .
C10 C 0.3902(3) 0.6824(2) 0.44577(7) 0.0219(5) Uani 1 1 d . . . . .
H10 H 0.340848 0.725247 0.463725 0.026 Uiso 1 1 calc R U . . .
C11 C 0.5602(3) 0.8697(2) 0.35975(7) 0.0213(5) Uani 1 1 d . . . . .
C12 C 0.6379(3) 0.9449(2) 0.38462(7) 0.0252(5) Uani 1 1 d . . . . .
H12 H 0.708145 0.914077 0.403694 0.030 Uiso 1 1 calc R U . . .
C13 C 0.6131(3) 1.0656(2) 0.38171(8) 0.0287(6) Uani 1 1 d . . . . .
H13 H 0.662230 1.116838 0.399356 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5162(4) 1.1110(2) 0.35286(8) 0.0301(6) Uani 1 1 d . . . . .
H14 H 0.500677 1.193476 0.350731 0.036 Uiso 1 1 calc R U . . .
C15 C 0.4425(4) 1.0372(2) 0.32734(8) 0.0278(6) Uani 1 1 d . . . . .
H15 H 0.378549 1.068710 0.307424 0.033 Uiso 1 1 calc R U . . .
C16 C 0.4628(3) 0.9159(2) 0.33099(7) 0.0235(5) Uani 1 1 d . . . . .
C17 C 0.6376(3) 0.6885(2) 0.33167(7) 0.0216(5) Uani 1 1 d . . . . .
C18 C 0.7782(3) 0.6175(2) 0.33378(7) 0.0256(5) Uani 1 1 d . . . . .
H18 H 0.838307 0.604329 0.356004 0.031 Uiso 1 1 calc R U . . .
C19 C 0.8309(4) 0.5659(2) 0.30347(8) 0.0285(6) Uani 1 1 d . . . . .
H19 H 0.926564 0.516863 0.305116 0.034 Uiso 1 1 calc R U . . .
C20 C 0.7453(4) 0.5853(2) 0.27077(8) 0.0301(6) Uani 1 1 d . . . . .
H20 H 0.781172 0.548882 0.250160 0.036 Uiso 1 1 calc R U . . .
C21 C 0.6070(4) 0.6582(2) 0.26837(7) 0.0261(5) Uani 1 1 d . . . . .
H21 H 0.549772 0.673335 0.245965 0.031 Uiso 1 1 calc R U . . .
C22 C 0.5519(3) 0.7091(2) 0.29864(7) 0.0230(5) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C22 1.909(3) . ?
Se1 C16 1.915(3) . ?
N1 C8 1.404(3) . ?
N1 C17 1.432(3) . ?
N1 C11 1.436(3) . ?
N2 C1 1.340(3) 2_556 ?
N2 C1 1.340(3) . ?
N3 C2 1.345(3) . ?
N3 C2 1.345(3) 2_556 ?
C1 C2 1.432(4) . ?
C1 C6 1.438(4) . ?
C2 C3 1.437(4) . ?
C3 C4 1.351(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.451(3) . ?
C4 H4 0.9500 . ?
C5 C7 1.407(4) . ?
C5 C6 1.407(4) . ?
C6 C10 1.411(3) . ?
C7 C8 1.400(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.414(4) . ?
C9 C10 1.370(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.386(4) . ?
C11 C16 1.395(4) . ?
C12 C13 1.392(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.397(4) . ?
C15 H15 0.9500 . ?
C17 C18 1.389(4) . ?
C17 C22 1.401(4) . ?
C18 C19 1.387(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(4) . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 Se1 C16 93.11(11) . . ?
C8 N1 C17 122.3(2) . . ?
C8 N1 C11 121.3(2) . . ?
C17 N1 C11 115.6(2) . . ?
C1 N2 C1 117.0(3) 2_556 . ?
C2 N3 C2 116.8(3) . 2_556 ?
N2 C1 C2 121.6(2) . . ?
N2 C1 C6 118.6(2) . . ?
C2 C1 C6 119.8(2) . . ?
N3 C2 C1 121.5(2) . . ?
N3 C2 C3 120.2(2) . . ?
C1 C2 C3 118.3(2) . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 121.8(2) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C7 C5 C6 120.3(2) . . ?
C7 C5 C4 121.5(2) . . ?
C6 C5 C4 118.2(2) . . ?
C5 C6 C10 118.4(2) . . ?
C5 C6 C1 120.4(2) . . ?
C10 C6 C1 121.2(2) . . ?
C8 C7 C5 120.9(2) . . ?
C8 C7 H7 119.6 . . ?
C5 C7 H7 119.6 . . ?
C7 C8 N1 122.4(2) . . ?
C7 C8 C9 117.9(2) . . ?
N1 C8 C9 119.7(2) . . ?
C10 C9 C8 121.5(2) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C6 121.0(2) . . ?
C9 C10 H10 119.5 . . ?
C6 C10 H10 119.5 . . ?
C12 C11 C16 119.6(2) . . ?
C12 C11 N1 121.1(2) . . ?
C16 C11 N1 119.3(2) . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 119.5(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C11 C16 C15 120.3(3) . . ?
C11 C16 Se1 118.35(18) . . ?
C15 C16 Se1 121.4(2) . . ?
C18 C17 C22 119.4(2) . . ?
C18 C17 N1 121.1(2) . . ?
C22 C17 N1 119.4(2) . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 119.6(3) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.1(2) . . ?
C21 C22 Se1 121.7(2) . . ?
C17 C22 Se1 118.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 C1 C2 -1.08(17) 2_556 . . . ?
C1 N2 C1 C6 178.1(3) 2_556 . . . ?
C2 N3 C2 C1 -1.08(17) 2_556 . . . ?
C2 N3 C2 C3 179.0(3) 2_556 . . . ?
N2 C1 C2 N3 2.3(4) . . . . ?
C6 C1 C2 N3 -176.94(19) . . . . ?
N2 C1 C2 C3 -177.8(2) . . . . ?
C6 C1 C2 C3 3.0(4) . . . . ?
N3 C2 C3 C4 178.0(2) . . . . ?
C1 C2 C3 C4 -1.9(4) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 C7 -175.6(3) . . . . ?
C3 C4 C5 C6 3.2(4) . . . . ?
C7 C5 C6 C10 -1.5(4) . . . . ?
C4 C5 C6 C10 179.7(2) . . . . ?
C7 C5 C6 C1 176.8(2) . . . . ?
C4 C5 C6 C1 -2.1(4) . . . . ?
N2 C1 C6 C5 179.8(2) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
N2 C1 C6 C10 -2.0(3) . . . . ?
C2 C1 C6 C10 177.2(2) . . . . ?
C6 C5 C7 C8 -0.5(4) . . . . ?
C4 C5 C7 C8 178.3(2) . . . . ?
C5 C7 C8 N1 -176.1(2) . . . . ?
C5 C7 C8 C9 2.3(4) . . . . ?
C17 N1 C8 C7 7.2(4) . . . . ?
C11 N1 C8 C7 176.3(2) . . . . ?
C17 N1 C8 C9 -171.1(2) . . . . ?
C11 N1 C8 C9 -2.0(4) . . . . ?
C7 C8 C9 C10 -2.1(4) . . . . ?
N1 C8 C9 C10 176.3(2) . . . . ?
C8 C9 C10 C6 0.1(4) . . . . ?
C5 C6 C10 C9 1.7(4) . . . . ?
C1 C6 C10 C9 -176.6(2) . . . . ?
C8 N1 C11 C12 63.9(3) . . . . ?
C17 N1 C11 C12 -126.3(3) . . . . ?
C8 N1 C11 C16 -118.2(3) . . . . ?
C17 N1 C11 C16 51.6(3) . . . . ?
C16 C11 C12 C13 2.7(4) . . . . ?
N1 C11 C12 C13 -179.4(2) . . . . ?
C11 C12 C13 C14 -2.9(4) . . . . ?
C12 C13 C14 C15 0.9(4) . . . . ?
C13 C14 C15 C16 1.4(4) . . . . ?
C12 C11 C16 C15 -0.4(4) . . . . ?
N1 C11 C16 C15 -178.3(2) . . . . ?
C12 C11 C16 Se1 178.72(19) . . . . ?
N1 C11 C16 Se1 0.8(3) . . . . ?
C14 C15 C16 C11 -1.6(4) . . . . ?
C14 C15 C16 Se1 179.3(2) . . . . ?
C8 N1 C17 C18 -64.1(3) . . . . ?
C11 N1 C17 C18 126.2(3) . . . . ?
C8 N1 C17 C22 118.5(3) . . . . ?
C11 N1 C17 C22 -51.2(3) . . . . ?
C22 C17 C18 C19 -1.2(4) . . . . ?
N1 C17 C18 C19 -178.5(2) . . . . ?
C17 C18 C19 C20 0.6(4) . . . . ?
C18 C19 C20 C21 0.8(4) . . . . ?
C19 C20 C21 C22 -1.7(4) . . . . ?
C20 C21 C22 C17 1.1(4) . . . . ?
C20 C21 C22 Se1 -179.6(2) . . . . ?
C18 C17 C22 C21 0.4(4) . . . . ?
N1 C17 C22 C21 177.8(2) . . . . ?
C18 C17 C22 Se1 -178.97(19) . . . . ?
N1 C17 C22 Se1 -1.6(3) . . . . ?


#==============================================================================
# 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        
3,11-di(10H-phenoselenazin-10-yl)dibenzo[a,j]phenazine
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane/ethyl acetate'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_xcalibur_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2061436'
loop_
_audit_author_name
_audit_author_address
'Youhei Takeda'
;Osaka University
Japan
;
_audit_update_record             
;
2021-02-19 deposited with the CCDC.	2021-08-20 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C44 H26 N4 Se2'
_chemical_formula_moiety         'C44 H26 N4 Se2'
_chemical_formula_weight         768.64
_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_
_space_group_symop_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                   8.24949(17)
_cell_length_b                   17.3233(3)
_cell_length_c                   22.8279(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.2052(19)
_cell_angle_gamma                90.0000
_cell_volume                     3261.58(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4794
_cell_measurement_theta_min      3.85
_cell_measurement_theta_max      72.96
_cell_measurement_temperature    213
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1544.00
_exptl_absorpt_coefficient_mu    3.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_T_max  0.969

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

_diffrn_ambient_temperature      213
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            20414
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_theta_max         74.486
_diffrn_reflns_theta_min         3.203
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6449
_reflns_number_gt                4353
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1472
_refine_ls_wR_factor_gt          0.1301
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6449
_refine_ls_number_parameters     451
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0815P)²] 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         0.82
_refine_diff_density_min         -0.73
_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 0.0181 0.0091
;
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 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.7943 1.1372
;
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_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se -0.29645(6) 0.70296(3) 0.16986(2) 0.05598(18) Uani 1 1 d . . . . .
Se2 Se 1.15979(6) 0.18044(3) 0.48818(2) 0.04484(16) Uani 1 1 d . . . . .
N1 N -0.0537(4) 0.5963(2) 0.24358(14) 0.0417(8) Uani 1 1 d . . . . .
N2 N 0.8260(4) 0.16576(19) 0.54565(13) 0.0384(8) Uani 1 1 d . . . . .
N3 N 0.3226(4) 0.43343(18) 0.46400(13) 0.0330(7) Uani 1 1 d . . . . .
N4 N 0.2530(4) 0.52260(19) 0.56434(14) 0.0357(7) Uani 1 1 d . . . . .
C1 C 0.2282(5) 0.4959(2) 0.46063(16) 0.0312(8) Uani 1 1 d . . . . .
C2 C 0.1600(5) 0.5194(2) 0.40372(16) 0.0323(8) Uani 1 1 d . . . . .
C3 C 0.0563(5) 0.5844(2) 0.40185(16) 0.0339(9) Uani 1 1 d . . . . .
C4 C 0.0201(5) 0.6263(2) 0.45419(17) 0.0367(9) Uani 1 1 d . . . . .
H4 H -0.051176 0.668594 0.452079 0.044 Uiso 1 1 calc R U . . .
C5 C 0.0866(5) 0.6059(2) 0.50631(17) 0.0385(9) Uani 1 1 d . . . . .
H5 H 0.063077 0.634793 0.539942 0.046 Uiso 1 1 calc R U . . .
C6 C 0.1920(5) 0.5411(2) 0.51100(17) 0.0346(9) Uani 1 1 d . . . . .
C7 C 0.1935(5) 0.4809(2) 0.35160(16) 0.0380(9) Uani 1 1 d . . . . .
H7 H 0.261816 0.437463 0.352449 0.046 Uiso 1 1 calc R U . . .
C8 C 0.1273(5) 0.5059(2) 0.29874(17) 0.0405(10) Uani 1 1 d . . . . .
H8 H 0.152579 0.480449 0.263723 0.049 Uiso 1 1 calc R U . . .
C9 C 0.0222(5) 0.5694(2) 0.29789(17) 0.0379(9) Uani 1 1 d . . . . .
C10 C -0.0115(5) 0.6079(2) 0.34776(17) 0.0369(9) Uani 1 1 d . . . . .
H10 H -0.081060 0.650910 0.346188 0.044 Uiso 1 1 calc R U . . .
C11 C 0.0192(5) 0.6594(2) 0.21526(16) 0.0383(9) Uani 1 1 d . . . . .
C12 C 0.1838(6) 0.6744(3) 0.22362(19) 0.0488(11) Uani 1 1 d . . . . .
H12 H 0.246862 0.640647 0.246927 0.059 Uiso 1 1 calc R U . . .
C13 C 0.2565(6) 0.7374(3) 0.1986(2) 0.0548(12) Uani 1 1 d . . . . .
H13 H 0.366997 0.747003 0.206422 0.066 Uiso 1 1 calc R U . . .
C14 C 0.1693(7) 0.7872(3) 0.1619(2) 0.0559(13) Uani 1 1 d . . . . .
H14 H 0.219894 0.829561 0.144114 0.067 Uiso 1 1 calc R U . . .
C15 C 0.0067(6) 0.7726(3) 0.15245(17) 0.0483(11) Uani 1 1 d . . . . .
H15 H -0.054132 0.805041 0.127374 0.058 Uiso 1 1 calc R U . . .
C16 C -0.0688(5) 0.7108(2) 0.17929(16) 0.0407(10) Uani 1 1 d . . . . .
C17 C -0.1990(5) 0.5598(2) 0.22543(16) 0.0385(9) Uani 1 1 d . . . . .
C18 C -0.2321(6) 0.4851(3) 0.24313(18) 0.0454(11) Uani 1 1 d . . . . .
H18 H -0.154938 0.458373 0.266215 0.054 Uiso 1 1 calc R U . . .
C19 C -0.3777(6) 0.4485(3) 0.22749(19) 0.0506(11) Uani 1 1 d . . . . .
H19 H -0.398950 0.398407 0.241102 0.061 Uiso 1 1 calc R U . . .
C20 C -0.4889(6) 0.4854(3) 0.1925(2) 0.0592(13) Uani 1 1 d . . . . .
H20 H -0.586069 0.460656 0.181358 0.071 Uiso 1 1 calc R U . . .
C21 C -0.4578(6) 0.5589(3) 0.17386(19) 0.0539(12) Uani 1 1 d . . . . .
H21 H -0.533214 0.583837 0.148884 0.065 Uiso 1 1 calc R U . . .
C22 C -0.3174(5) 0.5974(3) 0.19098(17) 0.0436(10) Uani 1 1 d . . . . .
C23 C 0.3820(4) 0.4141(2) 0.51763(15) 0.0310(8) Uani 1 1 d . . . . .
C24 C 0.4868(5) 0.3472(2) 0.52421(15) 0.0325(8) Uani 1 1 d . . . . .
C25 C 0.5526(5) 0.3300(2) 0.57997(15) 0.0316(8) Uani 1 1 d . . . . .
C26 C 0.5100(5) 0.3765(2) 0.62948(17) 0.0400(10) Uani 1 1 d . . . . .
H26 H 0.551326 0.363078 0.666794 0.048 Uiso 1 1 calc R U . . .
C27 C 0.4137(5) 0.4380(3) 0.62418(16) 0.0399(10) Uani 1 1 d . . . . .
H27 H 0.388814 0.467171 0.657537 0.048 Uiso 1 1 calc R U . . .
C28 C 0.3471(5) 0.4603(2) 0.56743(16) 0.0341(9) Uani 1 1 d . . . . .
C29 C 0.5293(5) 0.2998(2) 0.47733(16) 0.0361(9) Uani 1 1 d . . . . .
H29 H 0.484198 0.309715 0.439918 0.043 Uiso 1 1 calc R U . . .
C30 C 0.6351(5) 0.2393(2) 0.48459(16) 0.0377(9) Uani 1 1 d . . . . .
H30 H 0.659860 0.207824 0.452435 0.045 Uiso 1 1 calc R U . . .
C31 C 0.7075(5) 0.2238(2) 0.54036(15) 0.0316(8) Uani 1 1 d . . . . .
C32 C 0.6609(5) 0.2684(2) 0.58678(16) 0.0350(9) Uani 1 1 d . . . . .
H32 H 0.703194 0.257087 0.624377 0.042 Uiso 1 1 calc R U . . .
C33 C 0.9562(5) 0.1711(2) 0.58814(16) 0.0342(9) Uani 1 1 d . . . . .
C34 C 0.9279(6) 0.1649(2) 0.64756(17) 0.0412(10) Uani 1 1 d . . . . .
H34 H 0.822655 0.154267 0.660343 0.049 Uiso 1 1 calc R U . . .
C35 C 1.0530(6) 0.1741(2) 0.68822(18) 0.0467(11) Uani 1 1 d . . . . .
H35 H 1.031518 0.172013 0.728471 0.056 Uiso 1 1 calc R U . . .
C36 C 1.2081(6) 0.1864(2) 0.6700(2) 0.0525(13) Uani 1 1 d . . . . .
H36 H 1.292253 0.193879 0.697858 0.063 Uiso 1 1 calc R U . . .
C37 C 1.2415(5) 0.1878(2) 0.6109(2) 0.0446(10) Uani 1 1 d . . . . .
H37 H 1.348607 0.193775 0.598398 0.054 Uiso 1 1 calc R U . . .
C38 C 1.1140(5) 0.1803(2) 0.56988(16) 0.0356(9) Uani 1 1 d . . . . .
C39 C 0.8477(5) 0.1120(2) 0.49878(16) 0.0374(9) Uani 1 1 d . . . . .
C40 C 0.7217(6) 0.0608(2) 0.48488(18) 0.0438(10) Uani 1 1 d . . . . .
H40 H 0.626448 0.060547 0.506748 0.053 Uiso 1 1 calc R U . . .
C41 C 0.7398(6) 0.0105(2) 0.4383(2) 0.0486(12) Uani 1 1 d . . . . .
H41 H 0.655692 -0.023846 0.428114 0.058 Uiso 1 1 calc R U . . .
C42 C 0.8798(6) 0.0106(2) 0.40677(18) 0.0463(11) Uani 1 1 d . . . . .
H42 H 0.888766 -0.022731 0.374510 0.056 Uiso 1 1 calc R U . . .
C43 C 1.0066(6) 0.0583(2) 0.42146(17) 0.0420(10) Uani 1 1 d . . . . .
H43 H 1.103902 0.055958 0.400834 0.050 Uiso 1 1 calc R U . . .
C44 C 0.9892(5) 0.1103(2) 0.46754(16) 0.0380(10) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C16 1.890(4) . ?
Se1 C22 1.900(4) . ?
Se2 C44 1.910(4) . ?
Se2 C38 1.911(4) . ?
N1 C17 1.410(5) . ?
N1 C11 1.411(5) . ?
N1 C9 1.454(4) . ?
N2 C31 1.406(5) . ?
N2 C39 1.433(5) . ?
N2 C33 1.435(4) . ?
N3 C1 1.334(5) . ?
N3 C23 1.351(4) . ?
N4 C28 1.331(5) . ?
N4 C6 1.346(5) . ?
C1 C6 1.428(5) . ?
C1 C2 1.463(5) . ?
C2 C7 1.397(5) . ?
C2 C3 1.414(5) . ?
C3 C10 1.405(5) . ?
C3 C4 1.435(5) . ?
C4 C5 1.347(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.423(5) . ?
C5 H5 0.9400 . ?
C7 C8 1.383(5) . ?
C7 H7 0.9400 . ?
C8 C9 1.401(6) . ?
C8 H8 0.9400 . ?
C9 C10 1.354(5) . ?
C10 H10 0.9400 . ?
C11 C12 1.392(6) . ?
C11 C16 1.404(5) . ?
C12 C13 1.375(6) . ?
C12 H12 0.9400 . ?
C13 C14 1.392(7) . ?
C13 H13 0.9400 . ?
C14 C15 1.378(6) . ?
C14 H14 0.9400 . ?
C15 C16 1.388(6) . ?
C15 H15 0.9400 . ?
C17 C18 1.384(6) . ?
C17 C22 1.402(5) . ?
C18 C19 1.397(6) . ?
C18 H18 0.9400 . ?
C19 C20 1.362(6) . ?
C19 H19 0.9400 . ?
C20 C21 1.369(7) . ?
C20 H20 0.9400 . ?
C21 C22 1.385(6) . ?
C21 H21 0.9400 . ?
C23 C28 1.424(5) . ?
C23 C24 1.452(5) . ?
C24 C29 1.399(5) . ?
C24 C25 1.405(5) . ?
C25 C32 1.399(5) . ?
C25 C26 1.438(5) . ?
C26 C27 1.333(6) . ?
C26 H26 0.9400 . ?
C27 C28 1.449(5) . ?
C27 H27 0.9400 . ?
C29 C30 1.373(5) . ?
C29 H29 0.9400 . ?
C30 C31 1.420(5) . ?
C30 H30 0.9400 . ?
C31 C32 1.372(5) . ?
C32 H32 0.9400 . ?
C33 C38 1.384(6) . ?
C33 C34 1.385(5) . ?
C34 C35 1.383(5) . ?
C34 H34 0.9400 . ?
C35 C36 1.370(7) . ?
C35 H35 0.9400 . ?
C36 C37 1.384(6) . ?
C36 H36 0.9400 . ?
C37 C38 1.399(5) . ?
C37 H37 0.9400 . ?
C39 C44 1.381(6) . ?
C39 C40 1.397(6) . ?
C40 C41 1.386(6) . ?
C40 H40 0.9400 . ?
C41 C42 1.373(7) . ?
C41 H41 0.9400 . ?
C42 C43 1.369(6) . ?
C42 H42 0.9400 . ?
C43 C44 1.395(5) . ?
C43 H43 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 Se1 C22 97.79(19) . . ?
C44 Se2 C38 94.61(17) . . ?
C17 N1 C11 125.5(3) . . ?
C17 N1 C9 117.1(3) . . ?
C11 N1 C9 117.3(3) . . ?
C31 N2 C39 119.9(3) . . ?
C31 N2 C33 121.4(3) . . ?
C39 N2 C33 116.3(3) . . ?
C1 N3 C23 116.9(3) . . ?
C28 N4 C6 116.6(3) . . ?
N3 C1 C6 122.0(3) . . ?
N3 C1 C2 119.3(3) . . ?
C6 C1 C2 118.7(3) . . ?
C7 C2 C3 119.0(3) . . ?
C7 C2 C1 123.0(3) . . ?
C3 C2 C1 118.0(3) . . ?
C10 C3 C2 119.1(4) . . ?
C10 C3 C4 119.9(4) . . ?
C2 C3 C4 120.9(3) . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
N4 C6 C5 118.2(4) . . ?
N4 C6 C1 121.2(3) . . ?
C5 C6 C1 120.7(3) . . ?
C8 C7 C2 120.8(4) . . ?
C8 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
C7 C8 C9 119.4(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 120.9(4) . . ?
C10 C9 N1 117.8(4) . . ?
C8 C9 N1 121.3(4) . . ?
C9 C10 C3 120.7(4) . . ?
C9 C10 H10 119.6 . . ?
C3 C10 H10 119.6 . . ?
C12 C11 C16 116.9(4) . . ?
C12 C11 N1 120.4(3) . . ?
C16 C11 N1 122.6(4) . . ?
C13 C12 C11 121.6(4) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 121.2(5) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 118.0(5) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C14 C15 C16 121.2(4) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 121.1(4) . . ?
C15 C16 Se1 117.3(3) . . ?
C11 C16 Se1 121.4(3) . . ?
C18 C17 C22 117.3(4) . . ?
C18 C17 N1 120.3(4) . . ?
C22 C17 N1 122.3(4) . . ?
C17 C18 C19 121.5(4) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C20 C19 C18 120.1(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 119.4(4) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C21 C22 121.4(4) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C21 C22 C17 120.2(4) . . ?
C21 C22 Se1 118.1(3) . . ?
C17 C22 Se1 121.6(3) . . ?
N3 C23 C28 120.6(3) . . ?
N3 C23 C24 119.7(3) . . ?
C28 C23 C24 119.7(3) . . ?
C29 C24 C25 118.0(3) . . ?
C29 C24 C23 123.2(3) . . ?
C25 C24 C23 118.7(3) . . ?
C32 C25 C24 119.8(3) . . ?
C32 C25 C26 120.4(3) . . ?
C24 C25 C26 119.8(3) . . ?
C27 C26 C25 122.1(3) . . ?
C27 C26 H26 118.9 . . ?
C25 C26 H26 118.9 . . ?
C26 C27 C28 120.5(4) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
N4 C28 C23 122.7(3) . . ?
N4 C28 C27 118.3(3) . . ?
C23 C28 C27 119.0(3) . . ?
C30 C29 C24 121.7(3) . . ?
C30 C29 H29 119.2 . . ?
C24 C29 H29 119.2 . . ?
C29 C30 C31 120.4(4) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C32 C31 N2 122.8(3) . . ?
C32 C31 C30 117.9(3) . . ?
N2 C31 C30 119.4(3) . . ?
C31 C32 C25 122.1(3) . . ?
C31 C32 H32 118.9 . . ?
C25 C32 H32 118.9 . . ?
C38 C33 C34 118.9(4) . . ?
C38 C33 N2 120.0(3) . . ?
C34 C33 N2 121.1(4) . . ?
C35 C34 C33 120.6(4) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C36 C35 C34 120.2(4) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C35 C36 C37 120.3(4) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C36 C37 C38 119.3(4) . . ?
C36 C37 H37 120.4 . . ?
C38 C37 H37 120.4 . . ?
C33 C38 C37 120.5(4) . . ?
C33 C38 Se2 120.0(3) . . ?
C37 C38 Se2 119.5(3) . . ?
C44 C39 C40 120.2(4) . . ?
C44 C39 N2 121.3(4) . . ?
C40 C39 N2 118.5(4) . . ?
C41 C40 C39 118.8(4) . . ?
C41 C40 H40 120.6 . . ?
C39 C40 H40 120.6 . . ?
C42 C41 C40 120.5(4) . . ?
C42 C41 H41 119.8 . . ?
C40 C41 H41 119.8 . . ?
C43 C42 C41 121.3(4) . . ?
C43 C42 H42 119.4 . . ?
C41 C42 H42 119.4 . . ?
C42 C43 C44 119.0(4) . . ?
C42 C43 H43 120.5 . . ?
C44 C43 H43 120.5 . . ?
C39 C44 C43 120.3(4) . . ?
C39 C44 Se2 119.1(3) . . ?
C43 C44 Se2 120.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C23 N3 C1 C6 0.5(5) . . . . ?
C23 N3 C1 C2 -179.8(3) . . . . ?
N3 C1 C2 C7 -2.3(6) . . . . ?
C6 C1 C2 C7 177.4(4) . . . . ?
N3 C1 C2 C3 178.0(4) . . . . ?
C6 C1 C2 C3 -2.4(5) . . . . ?
C7 C2 C3 C10 0.6(6) . . . . ?
C1 C2 C3 C10 -179.6(4) . . . . ?
C7 C2 C3 C4 -179.3(4) . . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
C10 C3 C4 C5 -178.5(4) . . . . ?
C2 C3 C4 C5 1.4(6) . . . . ?
C3 C4 C5 C6 -1.4(6) . . . . ?
C28 N4 C6 C5 178.0(4) . . . . ?
C28 N4 C6 C1 -0.3(6) . . . . ?
C4 C5 C6 N4 -178.9(4) . . . . ?
C4 C5 C6 C1 -0.6(6) . . . . ?
N3 C1 C6 N4 0.4(6) . . . . ?
C2 C1 C6 N4 -179.3(4) . . . . ?
N3 C1 C6 C5 -177.9(4) . . . . ?
C2 C1 C6 C5 2.5(6) . . . . ?
C3 C2 C7 C8 0.4(6) . . . . ?
C1 C2 C7 C8 -179.3(4) . . . . ?
C2 C7 C8 C9 -1.7(6) . . . . ?
C7 C8 C9 C10 2.0(6) . . . . ?
C7 C8 C9 N1 -178.3(4) . . . . ?
C17 N1 C9 C10 -94.9(5) . . . . ?
C11 N1 C9 C10 81.7(5) . . . . ?
C17 N1 C9 C8 85.3(5) . . . . ?
C11 N1 C9 C8 -98.1(5) . . . . ?
C8 C9 C10 C3 -1.0(6) . . . . ?
N1 C9 C10 C3 179.3(4) . . . . ?
C2 C3 C10 C9 -0.3(6) . . . . ?
C4 C3 C10 C9 179.6(4) . . . . ?
C17 N1 C11 C12 -158.0(4) . . . . ?
C9 N1 C11 C12 25.7(6) . . . . ?
C17 N1 C11 C16 23.9(6) . . . . ?
C9 N1 C11 C16 -152.4(4) . . . . ?
C16 C11 C12 C13 1.1(6) . . . . ?
N1 C11 C12 C13 -177.1(4) . . . . ?
C11 C12 C13 C14 -2.6(7) . . . . ?
C12 C13 C14 C15 1.5(7) . . . . ?
C13 C14 C15 C16 0.9(7) . . . . ?
C14 C15 C16 C11 -2.4(7) . . . . ?
C14 C15 C16 Se1 173.3(3) . . . . ?
C12 C11 C16 C15 1.4(6) . . . . ?
N1 C11 C16 C15 179.5(4) . . . . ?
C12 C11 C16 Se1 -174.1(3) . . . . ?
N1 C11 C16 Se1 4.0(5) . . . . ?
C22 Se1 C16 C15 161.9(3) . . . . ?
C22 Se1 C16 C11 -22.5(4) . . . . ?
C11 N1 C17 C18 158.3(4) . . . . ?
C9 N1 C17 C18 -25.4(6) . . . . ?
C11 N1 C17 C22 -23.9(6) . . . . ?
C9 N1 C17 C22 152.4(4) . . . . ?
C22 C17 C18 C19 -0.1(6) . . . . ?
N1 C17 C18 C19 177.7(4) . . . . ?
C17 C18 C19 C20 2.1(7) . . . . ?
C18 C19 C20 C21 -1.1(8) . . . . ?
C19 C20 C21 C22 -1.7(8) . . . . ?
C20 C21 C22 C17 3.7(7) . . . . ?
C20 C21 C22 Se1 -173.2(4) . . . . ?
C18 C17 C22 C21 -2.7(6) . . . . ?
N1 C17 C22 C21 179.5(4) . . . . ?
C18 C17 C22 Se1 174.0(3) . . . . ?
N1 C17 C22 Se1 -3.7(6) . . . . ?
C16 Se1 C22 C21 -160.8(4) . . . . ?
C16 Se1 C22 C17 22.4(4) . . . . ?
C1 N3 C23 C28 -1.4(5) . . . . ?
C1 N3 C23 C24 -179.4(3) . . . . ?
N3 C23 C24 C29 -0.8(6) . . . . ?
C28 C23 C24 C29 -178.8(4) . . . . ?
N3 C23 C24 C25 177.5(4) . . . . ?
C28 C23 C24 C25 -0.5(5) . . . . ?
C29 C24 C25 C32 1.9(6) . . . . ?
C23 C24 C25 C32 -176.5(4) . . . . ?
C29 C24 C25 C26 -179.0(4) . . . . ?
C23 C24 C25 C26 2.6(6) . . . . ?
C32 C25 C26 C27 176.5(4) . . . . ?
C24 C25 C26 C27 -2.6(6) . . . . ?
C25 C26 C27 C28 0.3(7) . . . . ?
C6 N4 C28 C23 -0.7(6) . . . . ?
C6 N4 C28 C27 -179.4(4) . . . . ?
N3 C23 C28 N4 1.6(6) . . . . ?
C24 C23 C28 N4 179.6(4) . . . . ?
N3 C23 C28 C27 -179.7(4) . . . . ?
C24 C23 C28 C27 -1.7(6) . . . . ?
C26 C27 C28 N4 -179.3(4) . . . . ?
C26 C27 C28 C23 1.9(6) . . . . ?
C25 C24 C29 C30 -1.6(6) . . . . ?
C23 C24 C29 C30 176.7(4) . . . . ?
C24 C29 C30 C31 -1.2(6) . . . . ?
C39 N2 C31 C32 168.4(4) . . . . ?
C33 N2 C31 C32 -29.8(6) . . . . ?
C39 N2 C31 C30 -13.5(6) . . . . ?
C33 N2 C31 C30 148.3(4) . . . . ?
C29 C30 C31 C32 3.7(6) . . . . ?
C29 C30 C31 N2 -174.5(4) . . . . ?
N2 C31 C32 C25 174.7(4) . . . . ?
C30 C31 C32 C25 -3.4(6) . . . . ?
C24 C25 C32 C31 0.7(6) . . . . ?
C26 C25 C32 C31 -178.4(4) . . . . ?
C31 N2 C33 C38 -112.9(4) . . . . ?
C39 N2 C33 C38 49.5(5) . . . . ?
C31 N2 C33 C34 69.1(5) . . . . ?
C39 N2 C33 C34 -128.5(4) . . . . ?
C38 C33 C34 C35 5.4(6) . . . . ?
N2 C33 C34 C35 -176.6(4) . . . . ?
C33 C34 C35 C36 -2.8(6) . . . . ?
C34 C35 C36 C37 -1.5(6) . . . . ?
C35 C36 C37 C38 3.0(6) . . . . ?
C34 C33 C38 C37 -3.8(6) . . . . ?
N2 C33 C38 C37 178.2(3) . . . . ?
C34 C33 C38 Se2 174.7(3) . . . . ?
N2 C33 C38 Se2 -3.3(5) . . . . ?
C36 C37 C38 C33 -0.3(6) . . . . ?
C36 C37 C38 Se2 -178.9(3) . . . . ?
C31 N2 C39 C44 114.3(4) . . . . ?
C33 N2 C39 C44 -48.4(5) . . . . ?
C31 N2 C39 C40 -65.4(5) . . . . ?
C33 N2 C39 C40 131.9(4) . . . . ?
C44 C39 C40 C41 -2.0(6) . . . . ?
N2 C39 C40 C41 177.7(3) . . . . ?
C39 C40 C41 C42 0.6(6) . . . . ?
C40 C41 C42 C43 2.0(6) . . . . ?
C41 C42 C43 C44 -3.2(6) . . . . ?
C40 C39 C44 C43 0.7(5) . . . . ?
N2 C39 C44 C43 -179.0(3) . . . . ?
C40 C39 C44 Se2 -179.4(3) . . . . ?
N2 C39 C44 Se2 0.9(5) . . . . ?
C42 C43 C44 C39 1.9(6) . . . . ?
C42 C43 C44 Se2 -178.0(3) . . . . ?


#==============================================================================
# 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        
3,11-di(10H-phenoselenazin-10-yl)dibenzo[a,j]phenazine
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/n-hexane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_xcalibur_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2061435'
loop_
_audit_author_name
_audit_author_address
'Youhei Takeda'
;Osaka University
Japan
;
_audit_update_record             
;
2021-02-19 deposited with the CCDC.	2021-08-20 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C44 H26 N4 Se2'
_chemical_formula_moiety         'C44 H26 N4 Se2'
_chemical_formula_weight         768.64
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
#------------------------------------------------------------------------------
_cell_length_a                   30.3157(3)
_cell_length_b                   8.60933(10)
_cell_length_c                   26.5579(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.9262(11)
_cell_angle_gamma                90.0000
_cell_volume                     6894.51(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13073
_cell_measurement_theta_min      3.55
_cell_measurement_theta_max      73.72
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3088.00
_exptl_absorpt_coefficient_mu    2.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.240
_exptl_absorpt_correction_T_max  0.862

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

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            20846
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_theta_max         74.509
_diffrn_reflns_theta_min         3.346
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6866
_reflns_number_gt                6216
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1155
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6866
_refine_ls_number_parameters     451
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0565P)²+10.4448P] 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          0.002
_refine_diff_density_max         1.08
_refine_diff_density_min         -1.29
_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 0.0181 0.0091
;
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 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.7943 1.1372
;
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_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.41999(2) -0.02573(5) 0.36113(2) 0.08134(17) Uani 1 1 d . . . . .
Se2 Se 0.80967(2) 0.70598(3) 0.77366(2) 0.04631(11) Uani 1 1 d . . . . .
N1 N 0.50798(7) 0.1020(3) 0.42077(8) 0.0405(5) Uani 1 1 d . . . . .
N2 N 0.84106(6) 0.4533(3) 0.70486(7) 0.0357(4) Uani 1 1 d . . . . .
N3 N 0.73111(6) 0.5589(3) 0.42759(7) 0.0367(4) Uani 1 1 d . . . . .
N4 N 0.69907(6) 0.3872(2) 0.50679(6) 0.0303(4) Uani 1 1 d . . . . .
C1 C 0.69188(8) 0.4867(3) 0.42159(8) 0.0338(5) Uani 1 1 d . . . . .
C2 C 0.67576(7) 0.3986(3) 0.46115(8) 0.0304(5) Uani 1 1 d . . . . .
C3 C 0.63308(7) 0.3213(3) 0.45239(8) 0.0312(5) Uani 1 1 d . . . . .
C4 C 0.60870(8) 0.3361(3) 0.40415(8) 0.0340(5) Uani 1 1 d . . . . .
C5 C 0.62589(8) 0.4272(3) 0.36547(8) 0.0401(5) Uani 1 1 d . . . . .
H5 H 0.609005 0.436868 0.333443 0.048 Uiso 1 1 calc R U . . .
C6 C 0.66558(8) 0.4996(3) 0.37346(9) 0.0402(6) Uani 1 1 d . . . . .
H6 H 0.676167 0.559367 0.347144 0.048 Uiso 1 1 calc R U . . .
C7 C 0.61518(8) 0.2342(3) 0.49001(9) 0.0361(5) Uani 1 1 d . . . . .
H7 H 0.631497 0.223216 0.522323 0.043 Uiso 1 1 calc R U . . .
C8 C 0.57423(8) 0.1642(3) 0.48072(9) 0.0390(5) Uani 1 1 d . . . . .
H8 H 0.562195 0.107475 0.506771 0.047 Uiso 1 1 calc R U . . .
C9 C 0.55025(8) 0.1770(3) 0.43252(9) 0.0363(5) Uani 1 1 d . . . . .
C10 C 0.56744(8) 0.2617(3) 0.39534(9) 0.0365(5) Uani 1 1 d . . . . .
H10 H 0.551062 0.270088 0.362972 0.044 Uiso 1 1 calc R U . . .
C11 C 0.50818(9) -0.0599(3) 0.41132(9) 0.0386(5) Uani 1 1 d . . . . .
C12 C 0.54636(10) -0.1477(3) 0.42317(10) 0.0486(6) Uani 1 1 d . . . . .
H12 H 0.572297 -0.098599 0.438845 0.058 Uiso 1 1 calc R U . . .
C13 C 0.54736(14) -0.3036(4) 0.41270(13) 0.0634(9) Uani 1 1 d . . . . .
H13 H 0.574212 -0.359892 0.419975 0.076 Uiso 1 1 calc R U . . .
C14 C 0.50999(14) -0.3791(4) 0.39183(13) 0.0681(10) Uani 1 1 d . . . . .
H14 H 0.510742 -0.487487 0.385238 0.082 Uiso 1 1 calc R U . . .
C15 C 0.47146(13) -0.2962(4) 0.38056(12) 0.0605(8) Uani 1 1 d . . . . .
H15 H 0.445208 -0.348448 0.367238 0.073 Uiso 1 1 calc R U . . .
C16 C 0.47062(9) -0.1367(3) 0.38849(10) 0.0462(6) Uani 1 1 d . . . . .
C17 C 0.46936(8) 0.1870(3) 0.42919(9) 0.0356(5) Uani 1 1 d . . . . .
C18 C 0.47201(9) 0.3179(3) 0.45974(10) 0.0433(6) Uani 1 1 d . . . . .
H18 H 0.499804 0.346252 0.477133 0.052 Uiso 1 1 calc R U . . .
C19 C 0.43527(9) 0.4078(4) 0.46547(12) 0.0514(7) Uani 1 1 d . . . . .
H19 H 0.438276 0.498298 0.486027 0.062 Uiso 1 1 calc R U . . .
C20 C 0.39429(9) 0.3684(4) 0.44182(12) 0.0561(7) Uani 1 1 d . . . . .
H20 H 0.369068 0.431285 0.445469 0.067 Uiso 1 1 calc R U . . .
C21 C 0.39067(9) 0.2359(4) 0.41279(13) 0.0585(8) Uani 1 1 d . . . . .
H21 H 0.362418 0.205392 0.397091 0.070 Uiso 1 1 calc R U . . .
C22 C 0.42753(9) 0.1461(3) 0.40604(11) 0.0465(6) Uani 1 1 d . . . . .
C23 C 0.75439(8) 0.5481(3) 0.47322(8) 0.0342(5) Uani 1 1 d . . . . .
C24 C 0.73807(7) 0.4611(3) 0.51335(8) 0.0293(4) Uani 1 1 d . . . . .
C25 C 0.76430(7) 0.4559(3) 0.56231(8) 0.0296(4) Uani 1 1 d . . . . .
C26 C 0.80459(7) 0.5388(3) 0.56937(8) 0.0309(5) Uani 1 1 d . . . . .
C27 C 0.81957(8) 0.6242(3) 0.52757(9) 0.0388(5) Uani 1 1 d . . . . .
H27 H 0.846827 0.679302 0.532423 0.047 Uiso 1 1 calc R U . . .
C28 C 0.79577(8) 0.6276(3) 0.48176(9) 0.0414(6) Uani 1 1 d . . . . .
H28 H 0.806702 0.683706 0.454852 0.050 Uiso 1 1 calc R U . . .
C29 C 0.75081(7) 0.3720(3) 0.60304(8) 0.0339(5) Uani 1 1 d . . . . .
H29 H 0.723818 0.315141 0.598820 0.041 Uiso 1 1 calc R U . . .
C30 C 0.77606(8) 0.3703(3) 0.64924(8) 0.0352(5) Uani 1 1 d . . . . .
H30 H 0.766423 0.311257 0.676266 0.042 Uiso 1 1 calc R U . . .
C31 C 0.81598(7) 0.4550(3) 0.65699(8) 0.0302(4) Uani 1 1 d . . . . .
C32 C 0.82964(7) 0.5388(3) 0.61670(8) 0.0328(5) Uani 1 1 d . . . . .
H32 H 0.856365 0.597034 0.621330 0.039 Uiso 1 1 calc R U . . .
C33 C 0.82209(7) 0.3895(3) 0.74771(8) 0.0323(5) Uani 1 1 d . . . . .
C34 C 0.82116(9) 0.2299(3) 0.75524(9) 0.0401(5) Uani 1 1 d . . . . .
H34 H 0.834187 0.162380 0.732645 0.048 Uiso 1 1 calc R U . . .
C35 C 0.80124(9) 0.1684(3) 0.79574(9) 0.0427(6) Uani 1 1 d . . . . .
H35 H 0.800074 0.059159 0.800388 0.051 Uiso 1 1 calc R U . . .
C36 C 0.78304(8) 0.2675(3) 0.82937(9) 0.0423(6) Uani 1 1 d . . . . .
H36 H 0.768742 0.225681 0.856532 0.051 Uiso 1 1 calc R U . . .
C37 C 0.78565(8) 0.4258(3) 0.82348(9) 0.0401(5) Uani 1 1 d . . . . .
H37 H 0.774261 0.493346 0.847302 0.048 Uiso 1 1 calc R U . . .
C38 C 0.80500(7) 0.4866(3) 0.78259(9) 0.0344(5) Uani 1 1 d . . . . .
C39 C 0.87409(7) 0.5708(3) 0.71664(8) 0.0334(5) Uani 1 1 d . . . . .
C40 C 0.91534(8) 0.5587(3) 0.69848(9) 0.0414(6) Uani 1 1 d . . . . .
H40 H 0.922015 0.471098 0.678901 0.050 Uiso 1 1 calc R U . . .
C41 C 0.94663(8) 0.6740(4) 0.70888(10) 0.0459(6) Uani 1 1 d . . . . .
H41 H 0.974650 0.666205 0.696023 0.055 Uiso 1 1 calc R U . . .
C42 C 0.93736(9) 0.8004(3) 0.73785(11) 0.0469(6) Uani 1 1 d . . . . .
H42 H 0.958885 0.879970 0.744540 0.056 Uiso 1 1 calc R U . . .
C43 C 0.89693(9) 0.8119(3) 0.75717(10) 0.0421(6) Uani 1 1 d . . . . .
H43 H 0.890802 0.897998 0.777706 0.050 Uiso 1 1 calc R U . . .
C44 C 0.86520(8) 0.6966(3) 0.74641(9) 0.0351(5) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C16 1.888(3) . ?
Se1 C22 1.899(3) . ?
Se2 C44 1.901(2) . ?
Se2 C38 1.911(3) . ?
N1 C11 1.416(3) . ?
N1 C17 1.418(3) . ?
N1 C9 1.440(3) . ?
N2 C31 1.413(3) . ?
N2 C39 1.434(3) . ?
N2 C33 1.436(3) . ?
N3 C1 1.337(3) . ?
N3 C23 1.341(3) . ?
N4 C24 1.338(3) . ?
N4 C2 1.342(3) . ?
C1 C2 1.423(3) . ?
C1 C6 1.439(3) . ?
C2 C3 1.452(3) . ?
C3 C7 1.402(3) . ?
C3 C4 1.417(3) . ?
C4 C10 1.404(3) . ?
C4 C5 1.432(4) . ?
C5 C6 1.353(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.410(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(4) . ?
C11 C16 1.400(4) . ?
C12 C13 1.372(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(4) . ?
C15 H15 0.9500 . ?
C17 C18 1.386(4) . ?
C17 C22 1.396(3) . ?
C18 C19 1.378(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.375(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(4) . ?
C21 H21 0.9500 . ?
C23 C28 1.427(3) . ?
C23 C24 1.432(3) . ?
C24 C25 1.453(3) . ?
C25 C29 1.397(3) . ?
C25 C26 1.410(3) . ?
C26 C32 1.400(3) . ?
C26 C27 1.444(3) . ?
C27 C28 1.349(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.377(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.410(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.389(3) . ?
C32 H32 0.9500 . ?
C33 C38 1.387(3) . ?
C33 C34 1.390(4) . ?
C34 C35 1.391(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.390(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.375(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.389(3) . ?
C37 H37 0.9500 . ?
C39 C44 1.384(3) . ?
C39 C40 1.390(3) . ?
C40 C41 1.381(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.378(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.381(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.391(4) . ?
C43 H43 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 Se1 C22 96.43(12) . . ?
C44 Se2 C38 94.88(10) . . ?
C11 N1 C17 123.7(2) . . ?
C11 N1 C9 117.4(2) . . ?
C17 N1 C9 117.7(2) . . ?
C31 N2 C39 119.21(19) . . ?
C31 N2 C33 119.64(18) . . ?
C39 N2 C33 115.12(17) . . ?
C1 N3 C23 117.0(2) . . ?
C24 N4 C2 117.28(19) . . ?
N3 C1 C2 122.0(2) . . ?
N3 C1 C6 118.3(2) . . ?
C2 C1 C6 119.7(2) . . ?
N4 C2 C1 121.1(2) . . ?
N4 C2 C3 119.2(2) . . ?
C1 C2 C3 119.64(19) . . ?
C7 C3 C4 119.2(2) . . ?
C7 C3 C2 122.3(2) . . ?
C4 C3 C2 118.4(2) . . ?
C10 C4 C3 118.8(2) . . ?
C10 C4 C5 120.9(2) . . ?
C3 C4 C5 120.2(2) . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C8 C7 C3 120.9(2) . . ?
C8 C7 H7 119.5 . . ?
C3 C7 H7 119.5 . . ?
C7 C8 C9 119.9(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 N1 118.5(2) . . ?
C8 C9 N1 121.7(2) . . ?
C9 C10 C4 121.4(2) . . ?
C9 C10 H10 119.3 . . ?
C4 C10 H10 119.3 . . ?
C12 C11 C16 117.5(3) . . ?
C12 C11 N1 120.9(2) . . ?
C16 C11 N1 121.6(2) . . ?
C13 C12 C11 121.4(3) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 120.7(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 119.3(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.4(3) . . ?
C15 C16 Se1 117.9(2) . . ?
C11 C16 Se1 121.4(2) . . ?
C18 C17 C22 117.2(2) . . ?
C18 C17 N1 120.8(2) . . ?
C22 C17 N1 121.9(2) . . ?
C19 C18 C17 121.5(2) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 118.5(3) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C20 C21 C22 121.1(3) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C21 C22 C17 120.7(3) . . ?
C21 C22 Se1 118.0(2) . . ?
C17 C22 Se1 121.2(2) . . ?
N3 C23 C28 118.8(2) . . ?
N3 C23 C24 121.3(2) . . ?
C28 C23 C24 119.9(2) . . ?
N4 C24 C23 121.4(2) . . ?
N4 C24 C25 119.76(19) . . ?
C23 C24 C25 118.9(2) . . ?
C29 C25 C26 118.52(19) . . ?
C29 C25 C24 122.1(2) . . ?
C26 C25 C24 119.34(19) . . ?
C32 C26 C25 120.1(2) . . ?
C32 C26 C27 120.4(2) . . ?
C25 C26 C27 119.5(2) . . ?
C28 C27 C26 121.6(2) . . ?
C28 C27 H27 119.2 . . ?
C26 C27 H27 119.2 . . ?
C27 C28 C23 120.8(2) . . ?
C27 C28 H28 119.6 . . ?
C23 C28 H28 119.6 . . ?
C30 C29 C25 121.0(2) . . ?
C30 C29 H29 119.5 . . ?
C25 C29 H29 119.5 . . ?
C29 C30 C31 121.0(2) . . ?
C29 C30 H30 119.5 . . ?
C31 C30 H30 119.5 . . ?
C32 C31 C30 118.4(2) . . ?
C32 C31 N2 121.5(2) . . ?
C30 C31 N2 120.05(19) . . ?
C31 C32 C26 121.0(2) . . ?
C31 C32 H32 119.5 . . ?
C26 C32 H32 119.5 . . ?
C38 C33 C34 119.0(2) . . ?
C38 C33 N2 120.4(2) . . ?
C34 C33 N2 120.5(2) . . ?
C33 C34 C35 120.3(2) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
C36 C35 C34 119.8(3) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C37 C36 C35 120.3(2) . . ?
C37 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C36 C37 C38 119.8(2) . . ?
C36 C37 H37 120.1 . . ?
C38 C37 H37 120.1 . . ?
C33 C38 C37 120.8(2) . . ?
C33 C38 Se2 118.37(18) . . ?
C37 C38 Se2 120.82(19) . . ?
C44 C39 C40 119.5(2) . . ?
C44 C39 N2 120.2(2) . . ?
C40 C39 N2 120.3(2) . . ?
C41 C40 C39 120.1(3) . . ?
C41 C40 H40 120.0 . . ?
C39 C40 H40 120.0 . . ?
C42 C41 C40 120.2(2) . . ?
C42 C41 H41 119.9 . . ?
C40 C41 H41 119.9 . . ?
C41 C42 C43 120.3(2) . . ?
C41 C42 H42 119.9 . . ?
C43 C42 H42 119.9 . . ?
C42 C43 C44 119.6(3) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 H43 120.2 . . ?
C39 C44 C43 120.3(2) . . ?
C39 C44 Se2 118.88(18) . . ?
C43 C44 Se2 120.79(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C23 N3 C1 C2 -1.6(3) . . . . ?
C23 N3 C1 C6 178.4(2) . . . . ?
C24 N4 C2 C1 -0.4(3) . . . . ?
C24 N4 C2 C3 -179.53(19) . . . . ?
N3 C1 C2 N4 1.4(3) . . . . ?
C6 C1 C2 N4 -178.5(2) . . . . ?
N3 C1 C2 C3 -179.4(2) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
N4 C2 C3 C7 -0.2(3) . . . . ?
C1 C2 C3 C7 -179.3(2) . . . . ?
N4 C2 C3 C4 179.3(2) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C7 C3 C4 C10 -0.6(3) . . . . ?
C2 C3 C4 C10 179.9(2) . . . . ?
C7 C3 C4 C5 178.7(2) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C10 C4 C5 C6 179.9(2) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
N3 C1 C6 C5 179.3(2) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C4 C3 C7 C8 -0.5(4) . . . . ?
C2 C3 C7 C8 179.0(2) . . . . ?
C3 C7 C8 C9 1.4(4) . . . . ?
C7 C8 C9 C10 -1.3(4) . . . . ?
C7 C8 C9 N1 178.2(2) . . . . ?
C11 N1 C9 C10 102.3(3) . . . . ?
C17 N1 C9 C10 -89.9(3) . . . . ?
C11 N1 C9 C8 -77.1(3) . . . . ?
C17 N1 C9 C8 90.7(3) . . . . ?
C8 C9 C10 C4 0.2(4) . . . . ?
N1 C9 C10 C4 -179.3(2) . . . . ?
C3 C4 C10 C9 0.7(3) . . . . ?
C5 C4 C10 C9 -178.6(2) . . . . ?
C17 N1 C11 C12 -153.9(2) . . . . ?
C9 N1 C11 C12 13.1(3) . . . . ?
C17 N1 C11 C16 27.9(4) . . . . ?
C9 N1 C11 C16 -165.0(2) . . . . ?
C16 C11 C12 C13 0.3(4) . . . . ?
N1 C11 C12 C13 -177.9(3) . . . . ?
C11 C12 C13 C14 -2.5(5) . . . . ?
C12 C13 C14 C15 1.2(5) . . . . ?
C13 C14 C15 C16 2.3(5) . . . . ?
C14 C15 C16 C11 -4.4(4) . . . . ?
C14 C15 C16 Se1 168.9(2) . . . . ?
C12 C11 C16 C15 3.1(4) . . . . ?
N1 C11 C16 C15 -178.7(2) . . . . ?
C12 C11 C16 Se1 -169.98(19) . . . . ?
N1 C11 C16 Se1 8.2(3) . . . . ?
C22 Se1 C16 C15 157.2(2) . . . . ?
C22 Se1 C16 C11 -29.6(2) . . . . ?
C11 N1 C17 C18 150.0(2) . . . . ?
C9 N1 C17 C18 -17.0(4) . . . . ?
C11 N1 C17 C22 -32.2(4) . . . . ?
C9 N1 C17 C22 160.9(2) . . . . ?
C22 C17 C18 C19 -2.6(4) . . . . ?
N1 C17 C18 C19 175.4(3) . . . . ?
C17 C18 C19 C20 1.5(5) . . . . ?
C18 C19 C20 C21 0.8(5) . . . . ?
C19 C20 C21 C22 -2.0(5) . . . . ?
C20 C21 C22 C17 0.9(5) . . . . ?
C20 C21 C22 Se1 -175.2(3) . . . . ?
C18 C17 C22 C21 1.4(4) . . . . ?
N1 C17 C22 C21 -176.6(3) . . . . ?
C18 C17 C22 Se1 177.4(2) . . . . ?
N1 C17 C22 Se1 -0.6(4) . . . . ?
C16 Se1 C22 C21 -158.1(3) . . . . ?
C16 Se1 C22 C17 25.8(3) . . . . ?
C1 N3 C23 C28 -178.0(2) . . . . ?
C1 N3 C23 C24 0.8(3) . . . . ?
C2 N4 C24 C23 -0.4(3) . . . . ?
C2 N4 C24 C25 178.6(2) . . . . ?
N3 C23 C24 N4 0.2(3) . . . . ?
C28 C23 C24 N4 179.0(2) . . . . ?
N3 C23 C24 C25 -178.8(2) . . . . ?
C28 C23 C24 C25 0.0(3) . . . . ?
N4 C24 C25 C29 1.9(3) . . . . ?
C23 C24 C25 C29 -179.2(2) . . . . ?
N4 C24 C25 C26 -177.7(2) . . . . ?
C23 C24 C25 C26 1.2(3) . . . . ?
C29 C25 C26 C32 -1.5(3) . . . . ?
C24 C25 C26 C32 178.1(2) . . . . ?
C29 C25 C26 C27 179.0(2) . . . . ?
C24 C25 C26 C27 -1.4(3) . . . . ?
C32 C26 C27 C28 -179.1(2) . . . . ?
C25 C26 C27 C28 0.4(4) . . . . ?
C26 C27 C28 C23 0.9(4) . . . . ?
N3 C23 C28 C27 177.8(2) . . . . ?
C24 C23 C28 C27 -1.1(4) . . . . ?
C26 C25 C29 C30 0.3(3) . . . . ?
C24 C25 C29 C30 -179.3(2) . . . . ?
C25 C29 C30 C31 0.8(4) . . . . ?
C29 C30 C31 C32 -0.8(4) . . . . ?
C29 C30 C31 N2 179.2(2) . . . . ?
C39 N2 C31 C32 17.3(3) . . . . ?
C33 N2 C31 C32 168.6(2) . . . . ?
C39 N2 C31 C30 -162.7(2) . . . . ?
C33 N2 C31 C30 -11.3(3) . . . . ?
C30 C31 C32 C26 -0.4(3) . . . . ?
N2 C31 C32 C26 179.6(2) . . . . ?
C25 C26 C32 C31 1.6(3) . . . . ?
C27 C26 C32 C31 -178.9(2) . . . . ?
C31 N2 C33 C38 -100.9(3) . . . . ?
C39 N2 C33 C38 51.6(3) . . . . ?
C31 N2 C33 C34 80.1(3) . . . . ?
C39 N2 C33 C34 -127.4(2) . . . . ?
C38 C33 C34 C35 3.4(4) . . . . ?
N2 C33 C34 C35 -177.6(2) . . . . ?
C33 C34 C35 C36 -1.4(4) . . . . ?
C34 C35 C36 C37 -1.6(4) . . . . ?
C35 C36 C37 C38 2.6(4) . . . . ?
C34 C33 C38 C37 -2.5(3) . . . . ?
N2 C33 C38 C37 178.5(2) . . . . ?
C34 C33 C38 Se2 176.45(18) . . . . ?
N2 C33 C38 Se2 -2.6(3) . . . . ?
C36 C37 C38 C33 -0.5(4) . . . . ?
C36 C37 C38 Se2 -179.39(19) . . . . ?
C31 N2 C39 C44 100.9(2) . . . . ?
C33 N2 C39 C44 -51.7(3) . . . . ?
C31 N2 C39 C40 -79.5(3) . . . . ?
C33 N2 C39 C40 127.9(2) . . . . ?
C44 C39 C40 C41 -2.0(4) . . . . ?
N2 C39 C40 C41 178.4(2) . . . . ?
C39 C40 C41 C42 0.9(4) . . . . ?
C40 C41 C42 C43 0.7(4) . . . . ?
C41 C42 C43 C44 -1.3(4) . . . . ?
C40 C39 C44 C43 1.4(3) . . . . ?
N2 C39 C44 C43 -178.9(2) . . . . ?
C40 C39 C44 Se2 -176.94(18) . . . . ?
N2 C39 C44 Se2 2.7(3) . . . . ?
C42 C43 C44 C39 0.2(4) . . . . ?
C42 C43 C44 Se2 178.52(19) . . . . ?


#==============================================================================
# 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        
3,11-di(10H-phenoselenazin-10-yl)dibenzo[a,j]phenazine
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/ethyl acetate'
_exptl_crystal_preparation       Luminescent
