# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_20201204
_database_code_depnum_ccdc_archive 'CCDC 2057404'
loop_
_audit_author_name
_audit_author_address
SeBPH
;Tokyo metropolitan university
Japan
;
_audit_update_record             
;
2021-01-20 deposited with the CCDC.	2021-03-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 B2 F4 N4 Se2'
_chemical_formula_iupac          ?
_chemical_formula_weight         648.03

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   25.0876(11)
_cell_length_b                   5.2205(2)
_cell_length_c                   22.5474(9)
_cell_angle_alpha                90
_cell_angle_beta                 120.3860(10)
_cell_angle_gamma                90
_cell_volume                     2547.39(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8291
_cell_measurement_theta_min      3.5296
_cell_measurement_theta_max      66.5470
_cell_measurement_temperature    120.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1288

_exptl_absorpt_coefficient_mu    4.101
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_T_max  0.49

_exptl_special_details           
;
;

_diffrn_ambient_temperature      120.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            9290
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_theta_min         4.08
_diffrn_reflns_theta_max         66.54
_diffrn_reflns_theta_full        66.54
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             2160
_reflns_number_gt                2143
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0604
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_restrained_S_all      1.171
_refine_ls_number_reflns         2160
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+5.9672P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   isomor

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.320
_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 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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se Se1 0.34540(2) 0.74246(4) 0.58820(2) 0.01890(11) Uani d . . . 1 . .
B B1 0.40524(10) 0.0629(4) 0.44528(11) 0.0146(4) Uani d . . . 1 . .
F F1 0.39062(5) 0.2018(2) 0.38667(6) 0.0206(3) Uani d . . . 1 . .
N N1 0.40942(8) 0.2356(3) 0.50176(9) 0.0145(4) Uani d . . . 1 . .
C C1 0.33952(11) 0.2730(5) 0.76270(12) 0.0268(5) Uani d . . . 1 . .
H H00J 0.33774 0.180493 0.797938 0.032 Uiso calc U . R 1 . .
N N2 0.52701(7) 0.0565(3) 0.52628(8) 0.0139(3) Uani d . . . 1 . .
F F2 0.36495(5) -0.1381(2) 0.42973(6) 0.0202(3) Uani d . . . 1 . .
C C2 0.30393(10) 0.4892(5) 0.73483(11) 0.0265(5) Uani d . . . 1 . .
H H00K 0.277871 0.546656 0.751339 0.032 Uiso calc U . R 1 . .
C C3 0.30583(10) 0.6233(4) 0.68300(11) 0.0223(5) Uani d . . . 1 . .
H H3 0.280612 0.770473 0.663534 0.027 Uiso calc U . R 1 . .
C C4 0.34475(9) 0.5423(4) 0.65935(10) 0.0161(4) Uani d . . . 1 . .
C C5 0.38120(9) 0.3257(4) 0.68767(11) 0.0192(4) Uani d . . . 1 . .
H H5 0.408063 0.270258 0.672033 0.023 Uiso calc U . R 1 . .
C C6 0.37813(10) 0.1912(5) 0.73875(11) 0.0250(5) Uani d . . . 1 . .
H H00L 0.402589 0.041754 0.757675 0.03 Uiso calc U . R 1 . .
C C10 0.45409(9) 0.5151(4) 0.59194(10) 0.0154(4) Uani d . . . 1 . .
C C11 0.50080(10) 0.6657(4) 0.65260(11) 0.0211(4) Uani d . . . 1 . .
H H00B 0.540999 0.655122 0.65537 0.032 Uiso calc U . R 1 . .
H H11 0.504258 0.595356 0.694713 0.032 Uiso calc U . R 1 . .
H H00F 0.487723 0.845155 0.647451 0.032 Uiso calc U . R 1 . .
C C12 0.46563(9) 0.3337(4) 0.55358(10) 0.0142(4) Uani d . . . 1 . .
C C13 0.52105(9) 0.2416(4) 0.56227(10) 0.0148(4) Uani d . . . 1 . .
H H13 0.557943 0.318851 0.597241 0.018 Uiso calc U . R 1 . .
C C8 0.36337(9) 0.3525(4) 0.50584(10) 0.0157(4) Uani d . . . 1 . .
C C7 0.29711(10) 0.3022(5) 0.45556(11) 0.0214(4) Uani d . . . 1 . .
H H00G 0.289521 0.324601 0.408756 0.032 Uiso calc U . R 1 . .
H H00H 0.271372 0.422423 0.463513 0.032 Uiso calc U . R 1 . .
H H00I 0.28678 0.126325 0.461281 0.032 Uiso calc U . R 1 . .
C C9 0.39000(9) 0.5233(4) 0.56207(10) 0.0160(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Se1 C9 . 1.8906(19) ?
Se1 C4 . 1.922(2) ?
B1 F2 . 1.374(3) ?
B1 F1 . 1.384(3) ?
B1 N1 . 1.520(3) ?
B1 N2 5_656 1.608(3) ?
N1 C8 . 1.350(3) ?
N1 C12 . 1.396(3) ?
C1 C2 . 1.378(4) ?
C1 C6 . 1.393(4) ?
C1 H00J . 0.95 ?
N2 C13 . 1.318(3) ?
N2 N2 5_656 1.401(3) ?
C2 C3 . 1.384(3) ?
C2 H00K . 0.95 ?
C3 C4 . 1.394(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.390(3) ?
C5 C6 . 1.384(3) ?
C5 H5 . 0.95 ?
C6 H00L . 0.95 ?
C10 C9 . 1.395(3) ?
C10 C12 . 1.408(3) ?
C10 C11 . 1.497(3) ?
C11 H00B . 0.98 ?
C11 H11 . 0.98 ?
C11 H00F . 0.98 ?
C12 C13 . 1.388(3) ?
C13 H13 . 0.95 ?
C8 C9 . 1.411(3) ?
C8 C7 . 1.487(3) ?
C7 H00G . 0.98 ?
C7 H00H . 0.98 ?
C7 H00I . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 Se1 C4 . . 100.80(8) ?
F2 B1 F1 . . 110.55(16) ?
F2 B1 N1 . . 113.39(16) ?
F1 B1 N1 . . 111.23(17) ?
F2 B1 N2 . 5_656 107.36(16) ?
F1 B1 N2 . 5_656 107.45(15) ?
N1 B1 N2 . 5_656 106.54(15) ?
C8 N1 C12 . . 108.29(17) ?
C8 N1 B1 . . 128.78(17) ?
C12 N1 B1 . . 122.09(16) ?
C2 C1 C6 . . 119.4(2) ?
C2 C1 H00J . . 120.3 ?
C6 C1 H00J . . 120.3 ?
C13 N2 N2 . 5_656 117.83(19) ?
C13 N2 B1 . 5_656 117.69(16) ?
N2 N2 B1 5_656 5_656 123.31(19) ?
C1 C2 C3 . . 120.6(2) ?
C1 C2 H00K . . 119.7 ?
C3 C2 H00K . . 119.7 ?
C2 C3 C4 . . 120.0(2) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C5 C4 C3 . . 119.76(19) ?
C5 C4 Se1 . . 122.98(15) ?
C3 C4 Se1 . . 117.26(16) ?
C6 C5 C4 . . 119.6(2) ?
C6 C5 H5 . . 120.2 ?
C4 C5 H5 . . 120.2 ?
C5 C6 C1 . . 120.6(2) ?
C5 C6 H00L . . 119.7 ?
C1 C6 H00L . . 119.7 ?
C9 C10 C12 . . 105.61(17) ?
C9 C10 C11 . . 127.12(18) ?
C12 C10 C11 . . 127.26(18) ?
C10 C11 H00B . . 109.5 ?
C10 C11 H11 . . 109.5 ?
H00B C11 H11 . . 109.5 ?
C10 C11 H00F . . 109.5 ?
H00B C11 H00F . . 109.5 ?
H11 C11 H00F . . 109.5 ?
C13 C12 N1 . . 120.43(18) ?
C13 C12 C10 . . 130.45(19) ?
N1 C12 C10 . . 109.05(17) ?
N2 C13 C12 . . 125.76(19) ?
N2 C13 H13 . . 117.1 ?
C12 C13 H13 . . 117.1 ?
N1 C8 C9 . . 108.32(17) ?
N1 C8 C7 . . 122.22(18) ?
C9 C8 C7 . . 129.43(18) ?
C8 C7 H00G . . 109.5 ?
C8 C7 H00H . . 109.5 ?
H00G C7 H00H . . 109.5 ?
C8 C7 H00I . . 109.5 ?
H00G C7 H00I . . 109.5 ?
H00H C7 H00I . . 109.5 ?
C10 C9 C8 . . 108.70(17) ?
C10 C9 Se1 . . 125.98(15) ?
C8 C9 Se1 . . 125.20(15) ?

