# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_Compound_3a
_database_code_depnum_ccdc_archive 'CCDC 2214690'
loop_
_audit_author_name
_audit_author_address
'Ram Sunil Kumar Lalji'
;Kirori Mal College, University of Delhi
India
;
_audit_update_record             
;
2022-10-22 deposited with the CCDC.	2023-02-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT196_Compound_3a         
;
PROBLEM: No TEMP record and _measurement_temperature .NE.        293 Degree
RESPONSE: When the TEMP record is absent in the embedded .res file a   default temperature of 293K is assumed. An ALERT is issued when the CIF   reported _measurement_temperature differs from that value.
;
_vrf_PLAT910_Compound_3a         
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          6 Note
RESPONSE: This is because some of the reflections were effected by the beamstop.
;
# Added during the CSD deposition process: Saturday 22 October 2022 11:49 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O Se'
_chemical_formula_sum            'C22 H18 N2 O Se'
_chemical_formula_weight         405.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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

_cell_length_a                   11.2232(3)
_cell_length_b                   10.9897(2)
_cell_length_c                   15.9803(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.770(3)
_cell_angle_gamma                90
_cell_volume                     1854.83(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4533
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      29.2

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    2.037
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   NONE
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17099
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.280
_diffrn_reflns_theta_max         29.160
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4533
_reflns_number_gt                3584
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²+0.8003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4533
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0835
_refine_ls_wR_factor_gt          0.0761
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.3141(3) 0.4219(3) 0.52013(17) 0.0575(7) Uani 1 1 d . . . . .
H1 H 0.362151 0.360631 0.556080 0.069 Uiso 1 1 calc R U . . .
C2 C 0.2303(3) 0.4876(3) 0.54735(19) 0.0701(9) Uani 1 1 d . . . . .
H2 H 0.221911 0.470101 0.602020 0.084 Uiso 1 1 calc R U . . .
C3 C 0.1580(3) 0.5793(3) 0.4955(2) 0.0701(9) Uani 1 1 d . . . . .
H3 H 0.100872 0.622164 0.514979 0.084 Uiso 1 1 calc R U . . .
C4 C 0.1705(3) 0.6070(2) 0.41530(19) 0.0562(7) Uani 1 1 d . . . . .
H4 H 0.122130 0.669005 0.380443 0.067 Uiso 1 1 calc R U . . .
C5 C 0.2562(2) 0.5419(2) 0.38569(15) 0.0404(5) Uani 1 1 d . . . . .
C6 C 0.3269(2) 0.4476(2) 0.43762(15) 0.0426(5) Uani 1 1 d . . . . .
C7 C 0.4173(2) 0.4065(2) 0.32249(16) 0.0435(5) Uani 1 1 d . . . . .
C8 C 0.3481(2) 0.51648(19) 0.27801(14) 0.0371(5) Uani 1 1 d . . . . .
C9 C 0.4964(3) 0.2893(2) 0.46050(19) 0.0592(7) Uani 1 1 d . . . . .
H9A H 0.569394 0.281448 0.441363 0.071 Uiso 1 1 calc R U . . .
H9B H 0.526279 0.314651 0.522290 0.071 Uiso 1 1 calc R U . . .
C10 C 0.4318(3) 0.1691(3) 0.4525(2) 0.0714(8) Uani 1 1 d . . . . .
H10A H 0.489936 0.110191 0.488468 0.107 Uiso 1 1 calc R U . . .
H10B H 0.360364 0.176429 0.472350 0.107 Uiso 1 1 calc R U . . .
H10C H 0.403430 0.143262 0.391514 0.107 Uiso 1 1 calc R U . . .
C11 C 0.3720(2) 0.5622(2) 0.19775(14) 0.0380(5) Uani 1 1 d . . . . .
C12 C 0.3583(2) 0.4863(2) 0.12527(16) 0.0506(6) Uani 1 1 d . . . . .
H12 H 0.337720 0.404811 0.128312 0.061 Uiso 1 1 calc R U . . .
C13 C 0.3747(3) 0.5303(3) 0.04884(17) 0.0572(7) Uani 1 1 d . . . . .
H13 H 0.364139 0.479056 0.000574 0.069 Uiso 1 1 calc R U . . .
C14 C 0.4068(3) 0.6508(3) 0.04459(16) 0.0554(7) Uani 1 1 d . . . . .
H14 H 0.418600 0.680212 -0.006606 0.067 Uiso 1 1 calc R U . . .
C15 C 0.4216(2) 0.7278(2) 0.11533(15) 0.0456(6) Uani 1 1 d . . . . .
H15 H 0.443533 0.808788 0.111797 0.055 Uiso 1 1 calc R U . . .
C16 C 0.4036(2) 0.68470(19) 0.19216(14) 0.0361(5) Uani 1 1 d . . . . .
C17 C 0.5655(2) 0.88595(19) 0.28801(14) 0.0371(5) Uani 1 1 d . . . . .
C18 C 0.6768(2) 0.8289(2) 0.29090(17) 0.0495(6) Uani 1 1 d . . . . .
H18 H 0.680147 0.744430 0.289113 0.059 Uiso 1 1 calc R U . . .
C19 C 0.7830(2) 0.8968(3) 0.29645(17) 0.0543(6) Uani 1 1 d . . . . .
H19 H 0.856828 0.858375 0.296419 0.065 Uiso 1 1 calc R U . . .
C20 C 0.7788(3) 1.0212(3) 0.30200(17) 0.0576(7) Uani 1 1 d . . . . .
H20 H 0.850519 1.066951 0.306708 0.069 Uiso 1 1 calc R U . . .
C21 C 0.6696(3) 1.0788(2) 0.30064(19) 0.0595(7) Uani 1 1 d . . . . .
H21 H 0.667974 1.163057 0.305422 0.071 Uiso 1 1 calc R U . . .
C22 C 0.5617(2) 1.0114(2) 0.29217(16) 0.0486(6) Uani 1 1 d . . . . .
H22 H 0.486936 1.050603 0.289290 0.058 Uiso 1 1 calc R U . . .
N1 N 0.40930(19) 0.38395(18) 0.40550(13) 0.0467(5) Uani 1 1 d . . . . .
N2 N 0.27226(17) 0.57843(16) 0.30710(12) 0.0387(4) Uani 1 1 d . . . . .
O O 0.48096(19) 0.34361(17) 0.29058(13) 0.0630(5) Uani 1 1 d . . . . .
Se Se 0.41981(2) 0.79464(2) 0.28932(2) 0.04115(9) 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 1.368(4) . ?
C1 C6 1.403(3) . ?
C2 C3 1.381(4) . ?
C3 C4 1.370(4) . ?
C4 C5 1.402(3) . ?
C5 N2 1.387(3) . ?
C5 C6 1.396(3) . ?
C6 N1 1.388(3) . ?
C7 O 1.223(3) . ?
C7 N1 1.382(3) . ?
C7 C8 1.482(3) . ?
C8 N2 1.293(3) . ?
C8 C11 1.484(3) . ?
C9 C10 1.492(4) . ?
C9 N1 1.493(3) . ?
C11 C12 1.393(3) . ?
C11 C16 1.403(3) . ?
C12 C13 1.383(4) . ?
C13 C14 1.379(4) . ?
C14 C15 1.377(4) . ?
C15 C16 1.393(3) . ?
C16 Se 1.927(2) . ?
C17 C22 1.382(3) . ?
C17 C18 1.384(3) . ?
C17 Se 1.924(2) . ?
C18 C19 1.384(3) . ?
C19 C20 1.372(4) . ?
C20 C21 1.373(4) . ?
C21 C22 1.386(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
C2 C1 C6 119.5(3) . . ?
C1 C2 C3 121.5(3) . . ?
C4 C3 C2 119.9(3) . . ?
C3 C4 C5 120.1(3) . . ?
N2 C5 C6 122.0(2) . . ?
N2 C5 C4 118.2(2) . . ?
C6 C5 C4 119.7(2) . . ?
N1 C6 C5 118.1(2) . . ?
N1 C6 C1 122.6(2) . . ?
C5 C6 C1 119.3(2) . . ?
O C7 N1 122.4(2) . . ?
O C7 C8 123.1(2) . . ?
N1 C7 C8 114.4(2) . . ?
N2 C8 C7 124.0(2) . . ?
N2 C8 C11 117.78(19) . . ?
C7 C8 C11 118.18(19) . . ?
C10 C9 N1 111.3(2) . . ?
C12 C11 C16 118.7(2) . . ?
C12 C11 C8 121.0(2) . . ?
C16 C11 C8 120.24(19) . . ?
C13 C12 C11 121.0(2) . . ?
C14 C13 C12 119.6(2) . . ?
C15 C14 C13 120.7(2) . . ?
C14 C15 C16 120.1(2) . . ?
C15 C16 C11 119.9(2) . . ?
C15 C16 Se 119.64(17) . . ?
C11 C16 Se 120.49(16) . . ?
C22 C17 C18 119.5(2) . . ?
C22 C17 Se 118.67(18) . . ?
C18 C17 Se 121.58(17) . . ?
C17 C18 C19 120.4(2) . . ?
C20 C19 C18 119.6(3) . . ?
C19 C20 C21 120.5(3) . . ?
C20 C21 C22 120.1(2) . . ?
C17 C22 C21 119.8(2) . . ?
C7 N1 C6 122.15(19) . . ?
C7 N1 C9 116.6(2) . . ?
C6 N1 C9 121.2(2) . . ?
C8 N2 C5 118.46(19) . . ?
C17 Se C16 99.62(9) . . ?

_refine_diff_density_max         0.519
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_Compound_3c
_database_code_depnum_ccdc_archive 'CCDC 2215006'
loop_
_audit_author_name
_audit_author_address
'Ram Sunil Kumar Lalji'
;Kirori Mal College, University of Delhi
India
;
_audit_update_record             
;
2022-10-24 deposited with the CCDC.	2023-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 F N2 O Se'
_chemical_formula_sum            'C22 H17 F N2 O Se'
_chemical_formula_weight         423.33

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8962(7)
_cell_length_b                   10.3482(6)
_cell_length_c                   21.7111(10)
_cell_angle_alpha                99.181(5)
_cell_angle_beta                 91.413(5)
_cell_angle_gamma                114.770(7)
_cell_volume                     1982.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6978
_cell_measurement_theta_min      3.140
_cell_measurement_theta_max      23.9560

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            PALE-YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.916
_shelx_estimated_absorpt_T_min   0.689
_shelx_estimated_absorpt_T_max   0.724
_exptl_absorpt_correction_type   NONE
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20772
_diffrn_reflns_av_unetI/netI     0.1052
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.120
_diffrn_reflns_theta_max         29.225
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             9130
_reflns_number_gt                4826
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0306P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9130
_refine_ls_number_parameters     489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.46231(5) 0.11600(4) 0.25267(2) 0.05692(15) Uani 1 1 d . . . . .
Se2 Se 0.22647(5) 1.06781(4) 0.67351(2) 0.05818(16) Uani 1 1 d . . . . .
N1 N 0.1018(4) 0.7749(3) 0.59515(15) 0.0484(8) Uani 1 1 d . . . . .
F2 F 0.2607(4) 0.1460(3) 0.51540(13) 0.1030(11) Uani 1 1 d . . . . .
O1 O 0.1678(4) 0.5492(3) 0.69081(15) 0.0772(10) Uani 1 1 d . . . . .
N3 N 0.4794(4) 0.0642(3) 0.12207(15) 0.0551(9) Uani 1 1 d . . . . .
F1 F 0.6038(4) 1.5886(3) 0.87545(14) 0.1285(13) Uani 1 1 d . . . . .
N2 N 0.1924(4) 0.5483(3) 0.58563(18) 0.0602(10) Uani 1 1 d . . . . .
N4 N 0.3561(5) 0.1152(4) 0.01524(15) 0.0603(10) Uani 1 1 d . . . . .
O2 O 0.1217(4) -0.0274(4) 0.04050(14) 0.0866(10) Uani 1 1 d . . . . .
C16 C 0.1088(4) 0.9289(4) 0.72428(17) 0.0485(10) Uani 1 1 d . . . . .
C11 C 0.0652(4) 0.7780(4) 0.70466(17) 0.0437(9) Uani 1 1 d . . . . .
C10 C 0.1079(4) 0.7189(4) 0.64428(18) 0.0464(10) Uani 1 1 d . . . . .
C17 C 0.3392(5) 1.2305(4) 0.74122(18) 0.0508(10) Uani 1 1 d . . . . .
C27 C 0.5704(5) 0.1572(4) 0.0849(2) 0.0531(11) Uani 1 1 d . . . . .
C5 C 0.1432(5) 0.7220(4) 0.53837(19) 0.0537(11) Uani 1 1 d . . . . .
C32 C 0.3349(5) 0.0025(4) 0.10782(18) 0.0512(11) Uani 1 1 d . . . . .
C39 C 0.3985(5) 0.1283(4) 0.33662(19) 0.0537(11) Uani 1 1 d . . . . .
C33 C 0.2424(5) -0.0940(4) 0.14920(18) 0.0489(10) Uani 1 1 d . . . . .
C44 C 0.4790(5) 0.1105(4) 0.3859(2) 0.0588(12) Uani 1 1 d . . . . .
H44 H 0.561816 0.091754 0.378502 0.071 Uiso 1 1 calc R U . . .
C31 C 0.2602(6) 0.0259(5) 0.0521(2) 0.0600(12) Uani 1 1 d . . . . .
C37 C 0.2090(5) -0.1608(4) 0.2526(2) 0.0613(12) Uani 1 1 d . . . . .
H37 H 0.241503 -0.142074 0.294995 0.074 Uiso 1 1 calc R U . . .
C38 C 0.2900(5) -0.0621(4) 0.21509(19) 0.0505(11) Uani 1 1 d . . . . .
C15 C 0.0630(5) 0.9780(5) 0.78050(19) 0.0583(12) Uani 1 1 d . . . . .
H15 H 0.091863 1.076689 0.793552 0.070 Uiso 1 1 calc R U . . .
C9 C 0.1585(5) 0.6000(4) 0.6435(2) 0.0560(12) Uani 1 1 d . . . . .
C12 C -0.0231(5) 0.6829(5) 0.7423(2) 0.0621(12) Uani 1 1 d . . . . .
H12 H -0.051234 0.584052 0.730175 0.074 Uiso 1 1 calc R U . . .
C28 C 0.5118(5) 0.1852(4) 0.0312(2) 0.0566(11) Uani 1 1 d . . . . .
C6 C 0.1885(5) 0.6093(4) 0.5325(2) 0.0590(12) Uani 1 1 d . . . . .
C34 C 0.1110(5) -0.2208(4) 0.1260(2) 0.0641(13) Uani 1 1 d . . . . .
H34 H 0.076838 -0.241370 0.083730 0.077 Uiso 1 1 calc R U . . .
C4 C 0.1358(5) 0.7861(5) 0.4863(2) 0.0704(14) Uani 1 1 d . . . . .
H4 H 0.105041 0.860281 0.490638 0.085 Uiso 1 1 calc R U . . .
C42 C 0.3081(6) 0.1429(4) 0.4561(2) 0.0678(14) Uani 1 1 d . . . . .
C43 C 0.4341(6) 0.1212(4) 0.4463(2) 0.0657(13) Uani 1 1 d . . . . .
H43 H 0.489333 0.113569 0.479642 0.079 Uiso 1 1 calc R U . . .
C40 C 0.2709(5) 0.1530(4) 0.3480(2) 0.0661(13) Uani 1 1 d . . . . .
H40 H 0.217567 0.164940 0.315164 0.079 Uiso 1 1 calc R U . . .
C36 C 0.0817(6) -0.2856(5) 0.2283(2) 0.0727(14) Uani 1 1 d . . . . .
H36 H 0.029768 -0.349371 0.254236 0.087 Uiso 1 1 calc R U . . .
C14 C -0.0244(5) 0.8819(5) 0.8169(2) 0.0660(13) Uani 1 1 d . . . . .
H14 H -0.052926 0.916302 0.854143 0.079 Uiso 1 1 calc R U . . .
C26 C 0.7258(6) 0.2237(5) 0.1025(2) 0.0674(13) Uani 1 1 d . . . . .
H26 H 0.763927 0.204347 0.137689 0.081 Uiso 1 1 calc R U . . .
C35 C 0.0314(6) -0.3155(4) 0.1643(3) 0.0751(15) Uani 1 1 d . . . . .
H35 H -0.054858 -0.398228 0.147741 0.090 Uiso 1 1 calc R U . . .
C18 C 0.3122(6) 1.3528(4) 0.7504(2) 0.0714(14) Uani 1 1 d . . . . .
H18 H 0.234235 1.354235 0.726201 0.086 Uiso 1 1 calc R U . . .
C29 C 0.2857(6) 0.1357(5) -0.0422(2) 0.0792(15) Uani 1 1 d . . . . .
H29A H 0.190587 0.052525 -0.055747 0.095 Uiso 1 1 calc R U . . .
H29B H 0.349849 0.140913 -0.075653 0.095 Uiso 1 1 calc R U . . .
C7 C 0.2392(5) 0.4273(4) 0.5827(2) 0.0745(15) Uani 1 1 d . . . . .
H7A H 0.208081 0.367353 0.541175 0.089 Uiso 1 1 calc R U . . .
H7B H 0.188455 0.367463 0.612597 0.089 Uiso 1 1 calc R U . . .
C20 C 0.5152(6) 1.4698(5) 0.8306(2) 0.0772(16) Uani 1 1 d . . . . .
C41 C 0.2236(6) 0.1597(5) 0.4081(3) 0.0751(14) Uani 1 1 d . . . . .
H41 H 0.138829 0.174837 0.415805 0.090 Uiso 1 1 calc R U . . .
C13 C -0.0696(5) 0.7330(5) 0.7973(2) 0.0699(13) Uani 1 1 d . . . . .
H13 H -0.130453 0.667859 0.820870 0.084 Uiso 1 1 calc R U . . .
C22 C 0.4566(6) 1.2307(5) 0.7774(2) 0.0795(15) Uani 1 1 d . . . . .
H22 H 0.476452 1.149572 0.771391 0.095 Uiso 1 1 calc R U . . .
C23 C 0.6103(7) 0.2827(5) -0.0032(2) 0.0756(15) Uani 1 1 d . . . . .
H23 H 0.573198 0.304228 -0.038082 0.091 Uiso 1 1 calc R U . . .
C25 C 0.8219(6) 0.3172(5) 0.0678(3) 0.0799(16) Uani 1 1 d . . . . .
H25 H 0.924518 0.360138 0.079300 0.096 Uiso 1 1 calc R U . . .
C24 C 0.7640(7) 0.3472(5) 0.0151(3) 0.0843(17) Uani 1 1 d . . . . .
H24 H 0.828737 0.410878 -0.008056 0.101 Uiso 1 1 calc R U . . .
C3 C 0.1739(6) 0.7391(6) 0.4287(2) 0.0943(19) Uani 1 1 d . . . . .
H3 H 0.168414 0.780395 0.394272 0.113 Uiso 1 1 calc R U . . .
C8 C 0.4087(6) 0.4814(5) 0.5970(3) 0.0964(19) Uani 1 1 d . . . . .
H8A H 0.459747 0.541450 0.567818 0.145 Uiso 1 1 calc R U . . .
H8B H 0.432874 0.399978 0.593245 0.145 Uiso 1 1 calc R U . . .
H8C H 0.439507 0.536574 0.638924 0.145 Uiso 1 1 calc R U . . .
C1 C 0.2295(6) 0.5635(5) 0.4736(3) 0.0825(17) Uani 1 1 d . . . . .
H1 H 0.261763 0.490312 0.468846 0.099 Uiso 1 1 calc R U . . .
C21 C 0.5458(6) 1.3519(6) 0.8229(2) 0.0844(16) Uani 1 1 d . . . . .
H21 H 0.624278 1.351865 0.847318 0.101 Uiso 1 1 calc R U . . .
C19 C 0.4009(7) 1.4741(5) 0.7958(3) 0.0878(17) Uani 1 1 d . . . . .
H19 H 0.382389 1.555974 0.802099 0.105 Uiso 1 1 calc R U . . .
C30 C 0.2603(7) 0.2729(6) -0.0305(2) 0.1020(19) Uani 1 1 d . . . . .
H30A H 0.192963 0.266215 0.001196 0.153 Uiso 1 1 calc R U . . .
H30B H 0.217991 0.283247 -0.068626 0.153 Uiso 1 1 calc R U . . .
H30C H 0.354099 0.355536 -0.016674 0.153 Uiso 1 1 calc R U . . .
C2 C 0.2213(7) 0.6274(7) 0.4237(3) 0.101(2) Uani 1 1 d . . . . .
H2 H 0.247958 0.595908 0.385364 0.121 Uiso 1 1 calc R U . . .


_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 C39 1.946(4) . ?
Se1 C38 1.947(4) . ?
Se2 C17 1.948(4) . ?
Se2 C16 1.951(4) . ?
N1 C10 1.304(5) . ?
N1 C5 1.409(5) . ?
F2 C42 1.381(5) . ?
O1 C9 1.245(5) . ?
N3 C32 1.303(5) . ?
N3 C27 1.396(5) . ?
F1 C20 1.379(5) . ?
N2 C9 1.391(5) . ?
N2 C6 1.407(5) . ?
N2 C7 1.499(5) . ?
N4 C31 1.390(5) . ?
N4 C28 1.406(5) . ?
N4 C29 1.500(5) . ?
O2 C31 1.245(5) . ?
C16 C15 1.405(5) . ?
C16 C11 1.422(5) . ?
C11 C12 1.404(5) . ?
C11 C10 1.503(5) . ?
C10 C9 1.508(5) . ?
C17 C18 1.384(5) . ?
C17 C22 1.385(6) . ?
C27 C26 1.409(6) . ?
C27 C28 1.413(6) . ?
C5 C6 1.403(6) . ?
C5 C4 1.415(6) . ?
C32 C33 1.484(5) . ?
C32 C31 1.506(6) . ?
C39 C44 1.399(5) . ?
C39 C40 1.410(6) . ?
C33 C34 1.412(5) . ?
C33 C38 1.436(5) . ?
C44 C43 1.397(6) . ?
C37 C36 1.386(6) . ?
C37 C38 1.400(5) . ?
C15 C14 1.387(6) . ?
C12 C13 1.391(5) . ?
C28 C23 1.407(6) . ?
C6 C1 1.421(6) . ?
C34 C35 1.384(6) . ?
C4 C3 1.387(6) . ?
C42 C43 1.373(7) . ?
C42 C41 1.398(6) . ?
C40 C41 1.398(6) . ?
C36 C35 1.405(6) . ?
C14 C13 1.400(6) . ?
C26 C25 1.380(6) . ?
C18 C19 1.398(6) . ?
C29 C30 1.526(6) . ?
C7 C8 1.535(6) . ?
C20 C21 1.362(7) . ?
C20 C19 1.365(7) . ?
C22 C21 1.400(6) . ?
C23 C24 1.397(7) . ?
C25 C24 1.401(7) . ?
C3 C2 1.409(8) . ?
C1 C2 1.374(7) . ?

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
C39 Se1 C38 96.45(17) . . ?
C17 Se2 C16 98.38(16) . . ?
C10 N1 C5 118.9(3) . . ?
C32 N3 C27 119.3(4) . . ?
C9 N2 C6 122.0(3) . . ?
C9 N2 C7 116.9(4) . . ?
C6 N2 C7 121.1(3) . . ?
C31 N4 C28 122.0(4) . . ?
C31 N4 C29 116.9(4) . . ?
C28 N4 C29 121.1(4) . . ?
C15 C16 C11 119.2(4) . . ?
C15 C16 Se2 119.6(3) . . ?
C11 C16 Se2 121.1(3) . . ?
C12 C11 C16 118.5(3) . . ?
C12 C11 C10 119.9(3) . . ?
C16 C11 C10 121.6(3) . . ?
N1 C10 C11 118.2(3) . . ?
N1 C10 C9 123.1(4) . . ?
C11 C10 C9 118.7(3) . . ?
C18 C17 C22 118.9(4) . . ?
C18 C17 Se2 120.7(3) . . ?
C22 C17 Se2 120.2(3) . . ?
N3 C27 C26 117.6(4) . . ?
N3 C27 C28 122.3(4) . . ?
C26 C27 C28 120.1(4) . . ?
C6 C5 N1 122.3(4) . . ?
C6 C5 C4 120.5(4) . . ?
N1 C5 C4 117.2(4) . . ?
N3 C32 C33 117.5(4) . . ?
N3 C32 C31 122.8(4) . . ?
C33 C32 C31 119.7(4) . . ?
C44 C39 C40 119.8(4) . . ?
C44 C39 Se1 119.6(3) . . ?
C40 C39 Se1 120.6(3) . . ?
C34 C33 C38 117.9(4) . . ?
C34 C33 C32 122.5(4) . . ?
C38 C33 C32 119.6(3) . . ?
C43 C44 C39 119.5(4) . . ?
O2 C31 N4 121.8(4) . . ?
O2 C31 C32 122.6(5) . . ?
N4 C31 C32 115.6(4) . . ?
C36 C37 C38 121.8(4) . . ?
C37 C38 C33 118.9(4) . . ?
C37 C38 Se1 120.0(3) . . ?
C33 C38 Se1 121.1(3) . . ?
C14 C15 C16 121.2(4) . . ?
O1 C9 N2 121.6(4) . . ?
O1 C9 C10 123.0(4) . . ?
N2 C9 C10 115.4(4) . . ?
C13 C12 C11 121.6(4) . . ?
N4 C28 C23 123.1(5) . . ?
N4 C28 C27 117.9(4) . . ?
C23 C28 C27 119.0(5) . . ?
C5 C6 N2 118.2(4) . . ?
C5 C6 C1 118.5(5) . . ?
N2 C6 C1 123.2(4) . . ?
C35 C34 C33 122.1(4) . . ?
C3 C4 C5 120.5(5) . . ?
C43 C42 F2 119.1(5) . . ?
C43 C42 C41 122.6(5) . . ?
F2 C42 C41 118.3(5) . . ?
C42 C43 C44 119.7(4) . . ?
C41 C40 C39 120.7(4) . . ?
C37 C36 C35 119.7(4) . . ?
C15 C14 C13 119.8(4) . . ?
C25 C26 C27 120.4(5) . . ?
C34 C35 C36 119.5(4) . . ?
C17 C18 C19 120.7(5) . . ?
N4 C29 C30 112.3(3) . . ?
N2 C7 C8 112.9(3) . . ?
C21 C20 C19 122.5(4) . . ?
C21 C20 F1 118.2(6) . . ?
C19 C20 F1 119.3(5) . . ?
C40 C41 C42 117.7(5) . . ?
C12 C13 C14 119.7(4) . . ?
C17 C22 C21 120.6(4) . . ?
C24 C23 C28 119.8(5) . . ?
C26 C25 C24 119.6(5) . . ?
C23 C24 C25 121.0(5) . . ?
C4 C3 C2 118.4(5) . . ?
C2 C1 C6 119.9(5) . . ?
C20 C21 C22 118.6(5) . . ?
C20 C19 C18 118.6(4) . . ?
C1 C2 C3 122.1(5) . . ?

_refine_diff_density_max         0.558
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.070

