# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1977472'
loop_
_audit_author_name
_audit_author_address
'Li-Li Zhu'
;Zhoukou Normal University
China
;
_audit_update_record             
;
2020-01-14 deposited with the CCDC.	2020-02-12 downloaded from the CCDC.
;
_audit_creation_date             2020-01-14
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H29 N3 Se'
_chemical_formula_sum            'C27 H29 N3 Se'
_chemical_formula_weight         474.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.3492(16)
_cell_length_b                   13.4033(12)
_cell_length_c                   11.3497(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.454(4)
_cell_angle_gamma                90
_cell_volume                     2332.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8575
_cell_measurement_temperature    151(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.792
_shelx_estimated_absorpt_T_min   0.686
_exptl_absorpt_coefficient_mu    1.628
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0842 before and 0.0690 after correction.
The Ratio of minimum to maximum transmission is 0.3986.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            40020
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.461
_diffrn_reflns_theta_min         2.353
_diffrn_ambient_temperature      151.23
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker APEX-II diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3670
_reflns_number_total             4810
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.902
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4810
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0396P)²+3.9912P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1205
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15),
 C16(H16), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2339(2) 0.2815(2) 0.8794(3) 0.0331(7) Uani 1 1 d . . . . .
H1 H 0.215056 0.266366 0.956003 0.040 Uiso 1 1 calc R . . . .
C2 C 0.2027(2) 0.2363(2) 0.7751(3) 0.0295(7) Uani 1 1 d . . . . .
C3 C 0.1344(2) 0.1600(2) 0.7566(3) 0.0313(7) Uani 1 1 d . . . . .
C4 C 0.1332(2) 0.0955(3) 0.6601(3) 0.0346(8) Uani 1 1 d . . . . .
H4 H 0.177254 0.100579 0.604038 0.042 Uiso 1 1 calc R . . . .
C5 C 0.0685(2) 0.0241(3) 0.6451(3) 0.0385(8) Uani 1 1 d . . . . .
H5 H 0.068832 -0.019001 0.578674 0.046 Uiso 1 1 calc R . . . .
C6 C 0.0028(2) 0.0139(3) 0.7256(3) 0.0394(9) Uani 1 1 d . . . . .
C7 C 0.0039(2) 0.0790(3) 0.8218(3) 0.0382(8) Uani 1 1 d . . . . .
H7 H -0.040213 0.073968 0.877627 0.046 Uiso 1 1 calc R . . . .
C8 C 0.0685(2) 0.1507(3) 0.8370(3) 0.0363(8) Uani 1 1 d . . . . .
H8 H 0.067919 0.194247 0.903012 0.044 Uiso 1 1 calc R . . . .
C9 C -0.0665(3) -0.0647(3) 0.7094(4) 0.0496(10) Uani 1 1 d . . . . .
H9A H -0.083786 -0.070203 0.625531 0.074 Uiso 1 1 calc GR . . . .
H9B H -0.117245 -0.046127 0.754090 0.074 Uiso 1 1 calc GR . . . .
H9C H -0.043552 -0.128885 0.737969 0.074 Uiso 1 1 calc GR . . . .
C10 C 0.3564(2) 0.4084(2) 0.6734(3) 0.0323(7) Uani 1 1 d . . . . .
H10 H 0.396792 0.440896 0.733311 0.039 Uiso 1 1 calc R . . . .
C11 C 0.3076(2) 0.4918(2) 0.6078(3) 0.0312(7) Uani 1 1 d . . . . .
C12 C 0.2360(2) 0.4746(3) 0.5305(3) 0.0356(8) Uani 1 1 d . . . . .
H12 H 0.214026 0.408723 0.520492 0.043 Uiso 1 1 calc R . . . .
C13 C 0.1967(2) 0.5521(3) 0.4686(3) 0.0362(8) Uani 1 1 d . . . . .
H13 H 0.147419 0.538433 0.417681 0.043 Uiso 1 1 calc R . . . .
C14 C 0.2270(2) 0.6501(3) 0.4784(3) 0.0343(8) Uani 1 1 d . . . . .
C15 C 0.2984(2) 0.6671(3) 0.5553(3) 0.0361(8) Uani 1 1 d . . . . .
H15 H 0.320580 0.732967 0.564676 0.043 Uiso 1 1 calc R . . . .
C16 C 0.3382(2) 0.5892(3) 0.6191(3) 0.0350(8) Uani 1 1 d . . . . .
H16 H 0.386916 0.602860 0.671003 0.042 Uiso 1 1 calc R . . . .
C17 C 0.1817(3) 0.7336(3) 0.4063(3) 0.0391(8) Uani 1 1 d . . . . .
C18 C 0.1841(3) 0.7068(3) 0.2744(3) 0.0486(10) Uani 1 1 d . . . . .
H18A H 0.244732 0.697536 0.252952 0.073 Uiso 1 1 calc GR . . . .
H18B H 0.157650 0.760927 0.227091 0.073 Uiso 1 1 calc GR . . . .
H18C H 0.151435 0.644983 0.259338 0.073 Uiso 1 1 calc GR . . . .
C19 C 0.0859(3) 0.7420(3) 0.4406(4) 0.0464(9) Uani 1 1 d . . . . .
H19A H 0.056740 0.677625 0.428011 0.070 Uiso 1 1 calc GR . . . .
H19B H 0.056216 0.792991 0.391655 0.070 Uiso 1 1 calc GR . . . .
H19C H 0.083786 0.760854 0.523841 0.070 Uiso 1 1 calc GR . . . .
C20 C 0.2255(3) 0.8346(3) 0.4260(4) 0.0507(10) Uani 1 1 d . . . . .
H20A H 0.221785 0.853977 0.508900 0.076 Uiso 1 1 calc GR . . . .
H20B H 0.196077 0.884676 0.375651 0.076 Uiso 1 1 calc GR . . . .
H20C H 0.286920 0.829959 0.406221 0.076 Uiso 1 1 calc GR . . . .
C21 C 0.4130(2) 0.3477(3) 0.5926(3) 0.0342(8) Uani 1 1 d . . . . .
H21A H 0.443823 0.393645 0.540229 0.041 Uiso 1 1 calc R . . . .
H21B H 0.375197 0.303812 0.542349 0.041 Uiso 1 1 calc R . . . .
C22 C 0.5569(2) 0.3764(3) 0.7600(3) 0.0350(8) Uani 1 1 d . . . . .
C23 C 0.5981(2) 0.4491(3) 0.6957(3) 0.0400(8) Uani 1 1 d . . . . .
H23 H 0.600685 0.443213 0.612520 0.048 Uiso 1 1 calc R . . . .
C24 C 0.6352(3) 0.5300(3) 0.7535(4) 0.0498(10) Uani 1 1 d . . . . .
H24 H 0.662413 0.580479 0.709278 0.060 Uiso 1 1 calc R . . . .
C25 C 0.6335(3) 0.5388(3) 0.8743(4) 0.0491(10) Uani 1 1 d . . . . .
H25 H 0.659186 0.595075 0.912895 0.059 Uiso 1 1 calc R . . . .
C26 C 0.5943(3) 0.4657(3) 0.9387(4) 0.0503(10) Uani 1 1 d . . . . .
H26 H 0.594337 0.470650 1.022152 0.060 Uiso 1 1 calc R . . . .
C27 C 0.5548(3) 0.3848(3) 0.8818(3) 0.0431(9) Uani 1 1 d . . . . .
H27 H 0.526421 0.335289 0.926124 0.052 Uiso 1 1 calc R . . . .
N1 N 0.29453(19) 0.3495(2) 0.8547(2) 0.0340(6) Uani 1 1 d . . . . .
N2 N 0.29867(18) 0.3429(2) 0.7383(2) 0.0312(6) Uani 1 1 d . . . . .
N3 N 0.24550(18) 0.2760(2) 0.6854(2) 0.0303(6) Uani 1 1 d . . . . .
Se1 Se 0.49919(3) 0.26562(3) 0.68151(4) 0.04027(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.396(5) . ?
C1 N1 1.341(4) . ?
C2 C3 1.474(5) . ?
C2 N3 1.344(4) . ?
C3 C4 1.396(5) . ?
C3 C8 1.396(5) . ?
C4 C5 1.384(5) . ?
C5 C6 1.396(5) . ?
C6 C7 1.396(5) . ?
C6 C9 1.502(5) . ?
C7 C8 1.387(5) . ?
C10 C11 1.523(5) . ?
C10 C21 1.525(5) . ?
C10 N2 1.468(4) . ?
C11 C12 1.397(5) . ?
C11 C16 1.390(5) . ?
C12 C13 1.379(5) . ?
C13 C14 1.396(5) . ?
C14 C15 1.392(5) . ?
C14 C17 1.534(5) . ?
C15 C16 1.397(5) . ?
C17 C18 1.541(5) . ?
C17 C19 1.542(5) . ?
C17 C20 1.523(5) . ?
C21 Se1 1.966(3) . ?
C22 C23 1.386(5) . ?
C22 C27 1.388(5) . ?
C22 Se1 1.928(4) . ?
C23 C24 1.377(5) . ?
C24 C25 1.377(6) . ?
C25 C26 1.375(6) . ?
C26 C27 1.388(6) . ?
N1 N2 1.329(4) . ?
N2 N3 1.337(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 109.5(3) . . ?
C1 C2 C3 129.6(3) . . ?
N3 C2 C1 108.0(3) . . ?
N3 C2 C3 122.4(3) . . ?
C4 C3 C2 121.8(3) . . ?
C8 C3 C2 120.0(3) . . ?
C8 C3 C4 118.2(3) . . ?
C5 C4 C3 120.6(3) . . ?
C4 C5 C6 121.5(3) . . ?
C5 C6 C7 117.7(3) . . ?
C5 C6 C9 121.0(4) . . ?
C7 C6 C9 121.2(4) . . ?
C8 C7 C6 121.0(3) . . ?
C7 C8 C3 120.9(3) . . ?
C11 C10 C21 112.3(3) . . ?
N2 C10 C11 112.9(3) . . ?
N2 C10 C21 110.8(3) . . ?
C12 C11 C10 122.9(3) . . ?
C16 C11 C10 119.2(3) . . ?
C16 C11 C12 117.8(3) . . ?
C13 C12 C11 120.7(3) . . ?
C12 C13 C14 122.2(3) . . ?
C13 C14 C17 120.2(3) . . ?
C15 C14 C13 117.0(3) . . ?
C15 C14 C17 122.8(3) . . ?
C14 C15 C16 121.2(3) . . ?
C11 C16 C15 121.1(3) . . ?
C14 C17 C18 108.6(3) . . ?
C14 C17 C19 109.5(3) . . ?
C18 C17 C19 109.0(3) . . ?
C20 C17 C14 112.5(3) . . ?
C20 C17 C18 108.7(3) . . ?
C20 C17 C19 108.5(3) . . ?
C10 C21 Se1 112.2(2) . . ?
C23 C22 C27 119.9(3) . . ?
C23 C22 Se1 120.6(3) . . ?
C27 C22 Se1 119.5(3) . . ?
C24 C23 C22 119.4(4) . . ?
C23 C24 C25 121.1(4) . . ?
C26 C25 C24 119.7(4) . . ?
C25 C26 C27 120.1(4) . . ?
C26 C27 C22 119.9(4) . . ?
N2 N1 C1 103.0(3) . . ?
N1 N2 C10 121.0(3) . . ?
N1 N2 N3 115.9(3) . . ?
N3 N2 C10 123.1(3) . . ?
N2 N3 C2 103.6(3) . . ?
C22 Se1 C21 95.26(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1977473'
loop_
_audit_author_name
_audit_author_address
'Li-Li Zhu'
;Zhoukou Normal University
China
;
_audit_update_record             
;
2020-01-14 deposited with the CCDC.	2020-02-12 downloaded from the CCDC.
;
_audit_creation_date             2020-01-14
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H23 N3 Se'
_chemical_formula_sum            'C20 H23 N3 Se'
_chemical_formula_weight         384.37
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.6605(12)
_cell_length_b                   5.8592(7)
_cell_length_c                   13.2196(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.925(6)
_cell_angle_gamma                90
_cell_volume                     902.00(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2808
_cell_measurement_temperature    152(2)
_cell_measurement_theta_max      26.11
_cell_measurement_theta_min      3.09
_shelx_estimated_absorpt_T_max   0.745
_shelx_estimated_absorpt_T_min   0.623
_exptl_absorpt_coefficient_mu    2.087
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0879 before and 0.0574 after correction.
The Ratio of minimum to maximum transmission is 0.3514.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6654
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.192
_diffrn_reflns_theta_max         25.192
_diffrn_reflns_theta_min         2.390
_diffrn_ambient_temperature      151.67
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'Bruker APEX-II diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2707
_reflns_number_total             3170
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3170
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0104P)²+0.0474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0650
_refine_ls_wR_factor_ref         0.0679
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2839(5) 0.8811(9) 0.4463(4) 0.0362(13) Uani 1 1 d . . . . .
H1 H 0.249896 1.028312 0.448323 0.043 Uiso 1 1 calc R . . . .
C2 C 0.2470(5) 0.6892(9) 0.4970(4) 0.0355(13) Uani 1 1 d . . . . .
C3 C 0.1514(4) 0.6597(8) 0.5643(3) 0.0326(12) Uani 1 1 d . . . . .
C4 C 0.0697(4) 0.8309(9) 0.5730(3) 0.0339(14) Uani 1 1 d . . . . .
H4 H 0.074467 0.967637 0.534908 0.041 Uiso 1 1 calc R . . . .
C5 C -0.0195(4) 0.7996(15) 0.6384(3) 0.0378(12) Uani 1 1 d . . . . .
H5 H -0.073921 0.918412 0.645572 0.045 Uiso 1 1 calc R . . . .
C6 C -0.0303(5) 0.6049(9) 0.6916(4) 0.0415(13) Uani 1 1 d . . . . .
H6 H -0.092669 0.585687 0.734410 0.050 Uiso 1 1 calc R . . . .
C7 C 0.0506(5) 0.4328(9) 0.6832(4) 0.0398(13) Uani 1 1 d . . . . .
H7 H 0.043823 0.295756 0.720845 0.048 Uiso 1 1 calc R . . . .
C8 C 0.1404(5) 0.4596(9) 0.6208(4) 0.0361(12) Uani 1 1 d . . . . .
H8 H 0.195471 0.341126 0.615891 0.043 Uiso 1 1 calc R . . . .
C9 C 0.4817(5) 0.4751(10) 0.3704(4) 0.0422(13) Uani 1 1 d . . . . .
H9A H 0.481490 0.317891 0.397808 0.051 Uiso 1 1 calc R . . . .
H9B H 0.557089 0.544708 0.389654 0.051 Uiso 1 1 calc R . . . .
C10 C 0.4659(4) 0.4661(9) 0.2547(4) 0.0332(11) Uani 1 1 d . . . . .
H10 H 0.452409 0.625457 0.229717 0.040 Uiso 1 1 calc R . . . .
C11 C 0.5726(5) 0.3711(9) 0.2029(4) 0.0331(14) Uani 1 1 d . . . . .
C12 C 0.5538(5) 0.4020(10) 0.0886(4) 0.0433(14) Uani 1 1 d . . . . .
H12A H 0.548184 0.565062 0.072588 0.065 Uiso 1 1 calc GR . . . .
H12B H 0.482650 0.325192 0.065244 0.065 Uiso 1 1 calc GR . . . .
H12C H 0.618626 0.335523 0.054451 0.065 Uiso 1 1 calc GR . . . .
C13 C 0.5929(6) 0.1187(10) 0.2273(5) 0.0440(15) Uani 1 1 d . . . . .
H13A H 0.526935 0.029067 0.201003 0.066 Uiso 1 1 calc GR . . . .
H13B H 0.602168 0.098626 0.300889 0.066 Uiso 1 1 calc GR . . . .
H13C H 0.662443 0.066583 0.195742 0.066 Uiso 1 1 calc GR . . . .
C14 C 0.6803(5) 0.5063(9) 0.2375(4) 0.0411(13) Uani 1 1 d . . . . .
H14A H 0.699690 0.474016 0.309099 0.062 Uiso 1 1 calc GR . . . .
H14B H 0.665530 0.669898 0.228746 0.062 Uiso 1 1 calc GR . . . .
H14C H 0.744479 0.461169 0.196810 0.062 Uiso 1 1 calc GR . . . .
C15 C 0.2466(4) 0.4776(9) 0.1209(4) 0.0366(12) Uani 1 1 d . . . . .
C16 C 0.2019(5) 0.6869(9) 0.1467(4) 0.0429(14) Uani 1 1 d . . . . .
H16 H 0.215604 0.745508 0.213173 0.051 Uiso 1 1 calc R . . . .
C17 C 0.1370(5) 0.8111(15) 0.0752(4) 0.0493(15) Uani 1 1 d . . . . .
H17 H 0.106874 0.955431 0.093020 0.059 Uiso 1 1 calc R . . . .
C18 C 0.1155(5) 0.7275(11) -0.0216(4) 0.0500(19) Uani 1 1 d . . . . .
H18 H 0.070702 0.812786 -0.070322 0.060 Uiso 1 1 calc R . . . .
C19 C 0.1603(5) 0.5179(11) -0.0465(4) 0.0475(15) Uani 1 1 d . . . . .
H19 H 0.145739 0.458494 -0.112763 0.057 Uiso 1 1 calc R . . . .
C20 C 0.2261(5) 0.3933(10) 0.0238(4) 0.0416(13) Uani 1 1 d . . . . .
H20 H 0.257118 0.250081 0.005585 0.050 Uiso 1 1 calc R . . . .
N1 N 0.3743(4) 0.8255(9) 0.3944(3) 0.0410(13) Uani 1 1 d . . . . .
N2 N 0.3910(4) 0.6071(8) 0.4149(3) 0.0384(11) Uani 1 1 d . . . . .
N3 N 0.3163(4) 0.5140(7) 0.4758(3) 0.0370(10) Uani 1 1 d . . . . .
Se1 Se 0.32474(4) 0.28586(10) 0.22030(4) 0.04191(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.389(7) . ?
C1 N1 1.328(6) . ?
C2 C3 1.471(7) . ?
C2 N3 1.345(7) . ?
C3 C4 1.392(7) . ?
C3 C8 1.399(7) . ?
C4 C5 1.398(6) . ?
C5 C6 1.349(9) . ?
C6 C7 1.389(8) . ?
C7 C8 1.375(7) . ?
C9 C10 1.533(7) . ?
C9 N2 1.458(7) . ?
C10 C11 1.553(7) . ?
C10 Se1 1.989(5) . ?
C11 C12 1.527(7) . ?
C11 C13 1.530(7) . ?
C11 C14 1.534(7) . ?
C15 C16 1.382(7) . ?
C15 C20 1.384(7) . ?
C15 Se1 1.923(5) . ?
C16 C17 1.386(8) . ?
C17 C18 1.381(7) . ?
C18 C19 1.381(8) . ?
C19 C20 1.383(8) . ?
N1 N2 1.320(7) . ?
N2 N3 1.333(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 108.9(5) . . ?
C1 C2 C3 130.5(5) . . ?
N3 C2 C1 108.2(5) . . ?
N3 C2 C3 121.2(5) . . ?
C4 C3 C2 120.6(5) . . ?
C4 C3 C8 118.5(5) . . ?
C8 C3 C2 120.9(5) . . ?
C3 C4 C5 119.4(6) . . ?
C6 C5 C4 121.7(6) . . ?
C5 C6 C7 119.3(5) . . ?
C8 C7 C6 120.4(5) . . ?
C7 C8 C3 120.6(5) . . ?
N2 C9 C10 111.6(4) . . ?
C9 C10 C11 113.2(4) . . ?
C9 C10 Se1 107.6(3) . . ?
C11 C10 Se1 112.4(3) . . ?
C12 C11 C10 108.4(4) . . ?
C12 C11 C13 109.6(4) . . ?
C12 C11 C14 107.9(4) . . ?
C13 C11 C10 111.8(5) . . ?
C13 C11 C14 108.7(5) . . ?
C14 C11 C10 110.2(4) . . ?
C16 C15 C20 119.7(5) . . ?
C16 C15 Se1 121.4(4) . . ?
C20 C15 Se1 118.6(4) . . ?
C15 C16 C17 119.8(5) . . ?
C18 C17 C16 120.8(7) . . ?
C19 C18 C17 118.9(6) . . ?
C18 C19 C20 120.9(5) . . ?
C19 C20 C15 119.9(5) . . ?
N2 N1 C1 104.2(5) . . ?
N1 N2 C9 122.3(5) . . ?
N1 N2 N3 115.2(4) . . ?
N3 N2 C9 122.4(5) . . ?
N2 N3 C2 103.4(4) . . ?
C15 Se1 C10 101.7(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
