# 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_111
_database_code_depnum_ccdc_archive 'CCDC 2021616'
loop_
_audit_author_name
_audit_author_address
'Jin Jibiao'
;NJUPT
China
;
_audit_update_record             
;
2020-08-05 deposited with the CCDC.	2021-01-14 downloaded from the CCDC.
;
_audit_creation_date             2019-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        Orthorhombic
_chemical_formula_moiety         'C39 H25 B F2 N2 O2'
_chemical_formula_sum            'C39 H25 B F2 N2 O2'
_chemical_formula_weight         602.42
_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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   6.9869(11)
_cell_length_b                   19.139(3)
_cell_length_c                   22.504(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3009.3(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4861
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.187
_cell_measurement_theta_min      2.313
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            25027
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.356
_diffrn_reflns_theta_min         2.128
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1805
_reflns_number_total             3744
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    ?
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1888
_refine_ls_R_factor_gt           0.0942
_refine_ls_restrained_S_all      1.036
_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)+(0.0521P)²+3.3258P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1744
_refine_ls_wR_factor_ref         0.2124
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed U12: C3(0) B15(0)
 Fixed U23: C3(0) B15(0)
 Fixed Uiso: H3(0.068) H5(0.073) H7(0.081) H8(0.077) H9(0.074) H16(0.097)
 H17(0.115) H18(0.108) H20(0.14) H22(0.142) H23(0.123) H24(0.136) H25(0.132)
 Fixed X: C3(0) H3(0) H5(0.7028) H7(0.4624) H8(0.2121) H9(0.4504) B15(0)
 H16(0.7491) H17(1.235) H18(0.6705) H20(1.0973) H22(1.2019) H23(1.1978)
 H24(0.8386) H25(0.9604)
 Fixed Y: H3(-0.1091) H5(-0.0178) H7(-0.2061) H8(-0.1575) H9(0.0312) H16(-
 0.2392) H17(-0.2806) H18(-0.0405) H20(-0.0873) H22(-0.35) H23(-0.1766) H24(-
 0.0202) H25(-0.3306)
 Fixed Z: C3(0.25) H3(0.25) H5(0.3737) H7(0.3579) H8(0.3066) H9(0.3242)
 B15(0.25) H16(0.3095) H17(0.4462) H18(0.4813) H20(0.5945) H22(0.3642)
 H23(0.5353) H24(0.57) H25(0.2981)
;
_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
O1 O 0.1468(3) 0.04245(13) 0.27888(12) 0.0809(8) Uani 1 1 d . . . . .
N2 N 0.7613(4) -0.14622(16) 0.40343(12) 0.0633(8) Uani 1 1 d . . . . .
C3 C 0.0000 -0.0605(2) 0.2500 0.0568(12) Uani 1 2 d S T P . .
H3 H 0.0000 -0.1091 0.2500 0.068 Uiso 1 2 calc R U P . .
C4 C 0.3036(4) -0.05784(18) 0.30974(14) 0.0532(8) Uani 1 1 d . . . . .
C5 C 0.6026(5) -0.04589(19) 0.36069(15) 0.0612(9) Uani 1 1 d . . . . .
H5 H 0.7028 -0.0178 0.3737 0.073 Uiso 1 1 calc R U . . .
C6 C 0.1443(4) -0.02488(18) 0.27841(14) 0.0543(8) Uani 1 1 d . . . . .
C7 C 0.4598(5) -0.15824(19) 0.35108(16) 0.0679(10) Uani 1 1 d . . . . .
H7 H 0.4624 -0.2061 0.3579 0.081 Uiso 1 1 calc R U . . .
C8 C 0.3104(5) -0.12906(18) 0.32042(15) 0.0640(9) Uani 1 1 d . . . . .
H8 H 0.2121 -0.1575 0.3066 0.077 Uiso 1 1 calc R U . . .
C9 C 0.4526(5) -0.01676(18) 0.33070(15) 0.0616(9) Uani 1 1 d . . . . .
H9 H 0.4504 0.0312 0.3242 0.074 Uiso 1 1 calc R U . . .
C10 C 0.6061(4) -0.11660(18) 0.37178(14) 0.0569(8) Uani 1 1 d . . . . .
C11 C 0.9950(5) -0.1630(2) 0.47146(16) 0.0715(11) Uani 1 1 d . . . . .
C12 C 0.8389(5) -0.1207(2) 0.45641(15) 0.0689(10) Uani 1 1 d . . . . .
C13 C 1.0125(5) -0.2161(2) 0.42738(18) 0.0715(11) Uani 1 1 d . . . . .
C14 C 0.8656(5) -0.2048(2) 0.38601(16) 0.0628(9) Uani 1 1 d . . . . .
B15 B 0.0000 0.0835(3) 0.2500 0.0726(17) Uani 1 2 d S T P . .
C16 C 0.8455(6) -0.2469(2) 0.33723(19) 0.0812(12) Uani 1 1 d . . . . .
H16 H 0.7491 -0.2392 0.3095 0.097 Uiso 1 1 calc R U . . .
C17 C 1.1380(6) -0.2719(3) 0.4189(2) 0.0957(15) Uani 1 1 d . . . . .
H17 H 1.2350 -0.2806 0.4462 0.115 Uiso 1 1 calc R U . . .
C18 C 0.7757(7) -0.0676(2) 0.49176(17) 0.0900(13) Uani 1 1 d . . . . .
H18 H 0.6705 -0.0405 0.4813 0.108 Uiso 1 1 calc R U . . .
F19 F -0.0819(5) 0.1217(2) 0.29033(15) 0.201(2) Uani 1 1 d . . . . .
C20 C 1.0321(9) -0.0965(4) 0.5593(2) 0.117(2) Uani 1 1 d . . . . .
H20 H 1.0973 -0.0873 0.5945 0.140 Uiso 1 1 calc R U . . .
C22 C 1.1174(8) -0.3132(3) 0.3705(3) 0.1184(18) Uani 1 1 d . . . . .
H22 H 1.2019 -0.3500 0.3642 0.142 Uiso 1 1 calc R U . . .
C23 C 1.0929(7) -0.1496(3) 0.5243(2) 0.1029(17) Uani 1 1 d . . . . .
H23 H 1.1978 -0.1766 0.5353 0.123 Uiso 1 1 calc R U . . .
C24 C 0.8768(9) -0.0559(3) 0.5446(2) 0.1131(18) Uani 1 1 d . . . . .
H24 H 0.8386 -0.0202 0.5700 0.136 Uiso 1 1 calc R U . . .
C25 C 0.9728(8) -0.3011(2) 0.3307(2) 0.1098(16) Uani 1 1 d . . . . .
H25 H 0.9604 -0.3306 0.2981 0.132 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
O1 C6 1.289(4) . ?
O1 B15 1.446(4) . ?
N2 C10 1.416(4) . ?
N2 C12 1.397(4) . ?
N2 C14 1.394(4) . ?
C3 C6 1.375(4) 4 ?
C3 C6 1.375(4) . ?
C4 C6 1.461(4) . ?
C4 C8 1.385(4) . ?
C4 C9 1.387(4) . ?
C5 C9 1.365(4) . ?
C5 C10 1.376(5) . ?
C7 C8 1.370(4) . ?
C7 C10 1.378(4) . ?
C11 C12 1.400(5) . ?
C11 C13 1.425(5) . ?
C11 C23 1.397(5) . ?
C12 C18 1.365(5) . ?
C13 C14 1.402(5) . ?
C13 C17 1.395(6) . ?
C14 C16 1.369(5) . ?
B15 O1 1.446(4) 4 ?
B15 F19 1.298(4) . ?
B15 F19 1.298(4) 4 ?
C16 C25 1.374(6) . ?
C17 C22 1.353(7) . ?
C18 C24 1.401(6) . ?
C20 C23 1.354(7) . ?
C20 C24 1.375(7) . ?
C22 C25 1.369(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
C6 O1 B15 122.0(3) . . ?
C12 N2 C10 125.9(3) . . ?
C14 N2 C10 125.5(3) . . ?
C14 N2 C12 108.5(3) . . ?
C6 C3 C6 120.6(4) . 4 ?
C8 C4 C6 122.3(3) . . ?
C8 C4 C9 118.2(3) . . ?
C9 C4 C6 119.4(3) . . ?
C9 C5 C10 120.3(3) . . ?
O1 C6 C3 120.6(3) . . ?
O1 C6 C4 114.7(3) . . ?
C3 C6 C4 124.7(3) . . ?
C8 C7 C10 120.0(3) . . ?
C7 C8 C4 121.0(3) . . ?
C5 C9 C4 120.8(3) . . ?
C5 C10 N2 119.9(3) . . ?
C5 C10 C7 119.6(3) . . ?
C7 C10 N2 120.5(3) . . ?
C12 C11 C13 108.1(3) . . ?
C23 C11 C12 118.8(5) . . ?
C23 C11 C13 133.0(4) . . ?
N2 C12 C11 107.9(4) . . ?
C18 C12 N2 129.2(4) . . ?
C18 C12 C11 122.8(4) . . ?
C14 C13 C11 106.8(4) . . ?
C17 C13 C11 134.0(4) . . ?
C17 C13 C14 119.2(4) . . ?
N2 C14 C13 108.7(3) . . ?
C16 C14 N2 130.2(3) . . ?
C16 C14 C13 121.1(4) . . ?
O1 B15 O1 114.2(5) 4 . ?
F19 B15 O1 107.71(17) 4 4 ?
F19 B15 O1 107.71(17) . . ?
F19 B15 O1 107.9(2) . 4 ?
F19 B15 O1 107.9(2) 4 . ?
F19 B15 F19 111.5(7) 4 . ?
C14 C16 C25 117.6(4) . . ?
C22 C17 C13 119.3(4) . . ?
C12 C18 C24 116.8(5) . . ?
C23 C20 C24 122.1(5) . . ?
C17 C22 C25 120.4(5) . . ?
C20 C23 C11 118.7(5) . . ?
C20 C24 C18 120.8(5) . . ?
C22 C25 C16 122.4(5) . . ?

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
N2 C12 C18 C24 176.5(4) . . . . ?
N2 C14 C16 C25 178.8(4) . . . . ?
C6 O1 B15 O1 0.0(2) . . . 4 ?
C6 O1 B15 F19 -119.7(4) . . . 4 ?
C6 O1 B15 F19 119.8(5) . . . . ?
C6 C3 C6 O1 0.0(2) 4 . . . ?
C6 C3 C6 C4 -180.0(3) 4 . . . ?
C6 C4 C8 C7 -178.6(3) . . . . ?
C6 C4 C9 C5 179.3(3) . . . . ?
C8 C4 C6 O1 171.3(3) . . . . ?
C8 C4 C6 C3 -8.7(5) . . . . ?
C8 C4 C9 C5 0.4(5) . . . . ?
C8 C7 C10 N2 -179.9(3) . . . . ?
C8 C7 C10 C5 -1.0(5) . . . . ?
C9 C4 C6 O1 -7.5(4) . . . . ?
C9 C4 C6 C3 172.4(3) . . . . ?
C9 C4 C8 C7 0.3(5) . . . . ?
C9 C5 C10 N2 -179.4(3) . . . . ?
C9 C5 C10 C7 1.7(5) . . . . ?
C10 N2 C12 C11 -177.3(3) . . . . ?
C10 N2 C12 C18 6.6(6) . . . . ?
C10 N2 C14 C13 177.4(3) . . . . ?
C10 N2 C14 C16 -0.8(6) . . . . ?
C10 C5 C9 C4 -1.4(5) . . . . ?
C10 C7 C8 C4 0.0(5) . . . . ?
C11 C12 C18 C24 1.0(6) . . . . ?
C11 C13 C14 N2 0.6(4) . . . . ?
C11 C13 C14 C16 179.0(3) . . . . ?
C11 C13 C17 C22 -178.8(4) . . . . ?
C12 N2 C10 C5 47.5(5) . . . . ?
C12 N2 C10 C7 -133.6(4) . . . . ?
C12 N2 C14 C13 -1.1(4) . . . . ?
C12 N2 C14 C16 -179.3(4) . . . . ?
C12 C11 C13 C14 0.1(4) . . . . ?
C12 C11 C13 C17 -180.0(4) . . . . ?
C12 C11 C23 C20 0.6(6) . . . . ?
C12 C18 C24 C20 0.0(7) . . . . ?
C13 C11 C12 N2 -0.7(4) . . . . ?
C13 C11 C12 C18 175.6(3) . . . . ?
C13 C11 C23 C20 -175.4(4) . . . . ?
C13 C14 C16 C25 0.8(6) . . . . ?
C13 C17 C22 C25 -1.1(8) . . . . ?
C14 N2 C10 C5 -130.7(4) . . . . ?
C14 N2 C10 C7 48.2(5) . . . . ?
C14 N2 C12 C11 1.1(4) . . . . ?
C14 N2 C12 C18 -174.9(4) . . . . ?
C14 C13 C17 C22 1.1(6) . . . . ?
C14 C16 C25 C22 -0.8(7) . . . . ?
B15 O1 C6 C3 0.0(4) . . . . ?
B15 O1 C6 C4 180.0(2) . . . . ?
C17 C13 C14 N2 -179.3(3) . . . . ?
C17 C13 C14 C16 -1.0(5) . . . . ?
C17 C22 C25 C16 1.0(8) . . . . ?
C23 C11 C12 N2 -177.6(3) . . . . ?
C23 C11 C12 C18 -1.3(5) . . . . ?
C23 C11 C13 C14 176.3(4) . . . . ?
C23 C11 C13 C17 -3.7(7) . . . . ?
C23 C20 C24 C18 -0.7(8) . . . . ?
C24 C20 C23 C11 0.4(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
