# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_d8v20637
_database_code_depnum_ccdc_archive 'CCDC 2159995'
loop_
_audit_author_name
_audit_author_address
'Guangming Wang'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2022-07-17 downloaded from the CCDC.
;
_audit_creation_date             2022-01-25
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2021.12.21 svn.raa29eb21 for OlexSys, GUI svn.r6440)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H13 B F2 O3'
_chemical_formula_sum            'C16 H13 B F2 O3'
_chemical_formula_weight         302.07
_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'
F F 0.0171 0.0103 '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'

_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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   28.975(2)
_cell_length_b                   7.2581(5)
_cell_length_c                   6.7960(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1429.22(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2838
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.280
_cell_measurement_theta_min      6.278
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6622
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         3.139
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1187
_reflns_number_total             1505
_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 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.053(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.034
_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)+(0.0526P)²+0.2915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1296
_refine_special_details          
;
 ? 
;
_olex2_refinement_description    
;
1. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5)
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
F1 F 0.41704(4) 0.59544(14) 0.99113(13) 0.0693(4) Uani 1 1 d . . . . .
O1 O 0.38557(5) 0.7500 0.7237(2) 0.0583(5) Uani 1 2 d S T P . .
O2 O 0.46846(5) 0.7500 0.7896(2) 0.0607(5) Uani 1 2 d S T P . .
O3 O 0.66465(6) 0.7500 0.4142(3) 0.0904(8) Uani 1 2 d S T P . .
C1 C 0.35475(8) 0.7500 0.4042(4) 0.0648(7) Uani 1 2 d S T P . .
H1A H 0.3309 0.6737 0.4588 0.097 Uiso 0.5 1 calc R U P . .
H1B H 0.3637 0.7028 0.2778 0.097 Uiso 0.5 1 calc R U P . .
H1C H 0.3434 0.8736 0.3897 0.097 Uiso 0.5 1 calc R U P . .
C2 C 0.39539(8) 0.7500 0.5378(3) 0.0470(6) Uani 1 2 d S T P . .
C3 C 0.43991(8) 0.7500 0.4715(3) 0.0502(6) Uani 1 2 d S T P . .
H3 H 0.4458 0.7500 0.3370 0.060 Uiso 1 2 calc R U P . .
C4 C 0.47625(7) 0.7500 0.6030(3) 0.0423(5) Uani 1 2 d S T P . .
C5 C 0.52496(7) 0.7500 0.5459(3) 0.0421(5) Uani 1 2 d S T P . .
C6 C 0.53890(8) 0.7500 0.3500(3) 0.0488(6) Uani 1 2 d S T P . .
H6 H 0.5167 0.7500 0.2511 0.059 Uiso 1 2 calc R U P . .
C7 C 0.58521(8) 0.7500 0.2999(3) 0.0509(6) Uani 1 2 d S T P . .
H7 H 0.5942 0.7500 0.1686 0.061 Uiso 1 2 calc R U P . .
C8 C 0.61773(8) 0.7500 0.4476(3) 0.0553(6) Uani 1 2 d S T P . .
C9 C 0.60483(8) 0.7500 0.6428(4) 0.0668(8) Uani 1 2 d S T P . .
H9 H 0.6271 0.7500 0.7412 0.080 Uiso 1 2 calc R U P . .
C10 C 0.55879(8) 0.7500 0.6911(3) 0.0562(6) Uani 1 2 d S T P . .
H10 H 0.5501 0.7500 0.8228 0.067 Uiso 1 2 calc R U P . .
C11 C 0.68175(8) 0.7500 0.2227(4) 0.0615(7) Uani 1 2 d S T P . .
C12 C 0.69195(7) 0.5865(3) 0.1331(3) 0.0730(6) Uani 1 1 d . . . . .
H12 H 0.6846 0.4755 0.1941 0.088 Uiso 1 1 calc R U . . .
C13 C 0.71311(7) 0.5873(3) -0.0481(3) 0.0770(6) Uani 1 1 d . . . . .
H13 H 0.7201 0.4764 -0.1097 0.092 Uiso 1 1 calc R U . . .
C14 C 0.72391(9) 0.7500 -0.1379(4) 0.0741(8) Uani 1 2 d S T P . .
H14 H 0.7385 0.7500 -0.2597 0.089 Uiso 1 2 calc R U P . .
B1 B 0.42182(9) 0.7500 0.8786(4) 0.0510(7) Uani 1 2 d S T P . .


_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
F1 B1 1.3649(16) . ?
O1 C2 1.295(3) . ?
O1 B1 1.487(3) . ?
O2 C4 1.288(2) . ?
O2 B1 1.480(3) . ?
O3 C8 1.378(3) . ?
O3 C11 1.393(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.487(3) . ?
C2 C3 1.366(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(3) . ?
C4 C5 1.464(3) . ?
C5 C6 1.391(3) . ?
C5 C10 1.391(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.377(3) . ?
C8 C9 1.378(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(2) 7_575 ?
C11 C12 1.366(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(3) . ?
C14 C13 1.366(3) 7_575 ?
C14 H14 0.9300 . ?
B1 F1 1.3648(16) 7_575 ?

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 O1 B1 122.37(18) . . ?
C4 O2 B1 124.19(18) . . ?
C8 O3 C11 120.32(18) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 114.9(2) . . ?
O1 C2 C3 122.0(2) . . ?
C3 C2 C1 123.1(2) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
O2 C4 C3 120.22(19) . . ?
O2 C4 C5 115.47(18) . . ?
C3 C4 C5 124.31(19) . . ?
C6 C5 C4 122.25(19) . . ?
C6 C5 C10 118.3(2) . . ?
C10 C5 C4 119.43(19) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 118.9(2) . . ?
C8 C7 H7 120.5 . . ?
O3 C8 C9 115.2(2) . . ?
C7 C8 O3 123.7(2) . . ?
C7 C8 C9 121.1(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.5(2) . . ?
C10 C9 H9 120.2 . . ?
C5 C10 H10 119.5 . . ?
C9 C10 C5 121.0(2) . . ?
C9 C10 H10 119.5 . . ?
C12 C11 O3 119.56(12) . . ?
C12 C11 O3 119.56(12) 7_575 . ?
C12 C11 C12 120.6(2) 7_575 . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.4(2) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C13 119.7(3) 7_575 . ?
C13 C14 H14 120.2 7_575 . ?
C13 C14 H14 120.2 . . ?
F1 B1 F1 110.56(18) 7_575 . ?
F1 B1 O1 108.97(14) 7_575 . ?
F1 B1 O1 108.98(14) . . ?
F1 B1 O2 108.75(14) 7_575 . ?
F1 B1 O2 108.74(14) . . ?
O2 B1 O1 110.85(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1B F1 0.96 2.61 3.521(3) 159.2 1_554
C1 H1B F1 0.96 2.89 3.521(3) 124.5 7_574
C1 H1B F1 0.96 2.89 3.521(3) 124.5 7_574
C1 H1B F1 0.96 2.89 3.521(3) 124.5 7_574

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
O1 C2 C3 C4 0.000(0) . . . . ?
O2 C4 C5 C6 180.000(0) . . . . ?
O2 C4 C5 C10 0.000(0) . . . . ?
O3 C8 C9 C10 180.000(0) . . . . ?
O3 C11 C12 C13 -173.52(18) . . . . ?
C1 C2 C3 C4 180.000(0) . . . . ?
C2 O1 B1 F1 119.64(13) . . . 7_575 ?
C2 O1 B1 F1 -119.64(13) . . . . ?
C2 O1 B1 O2 0.000(0) . . . . ?
C2 C3 C4 O2 0.000(0) . . . . ?
C2 C3 C4 C5 180.000(0) . . . . ?
C3 C4 C5 C6 0.000(0) . . . . ?
C3 C4 C5 C10 180.000(0) . . . . ?
C4 O2 B1 F1 119.78(13) . . . . ?
C4 O2 B1 F1 -119.78(13) . . . 7_575 ?
C4 O2 B1 O1 0.000(0) . . . . ?
C4 C5 C6 C7 180.000(0) . . . . ?
C4 C5 C10 C9 180.000(0) . . . . ?
C5 C6 C7 C8 0.000(0) . . . . ?
C6 C5 C10 C9 0.000(0) . . . . ?
C6 C7 C8 O3 180.000(0) . . . . ?
C6 C7 C8 C9 0.000(0) . . . . ?
C7 C8 C9 C10 0.000(0) . . . . ?
C8 O3 C11 C12 92.89(19) . . . 7_575 ?
C8 O3 C11 C12 -92.88(19) . . . . ?
C8 C9 C10 C5 0.000(0) . . . . ?
C10 C5 C6 C7 0.000(0) . . . . ?
C11 O3 C8 C7 0.000(0) . . . . ?
C11 O3 C8 C9 180.000(0) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C11 C12 C13 0.6(4) 7_575 . . . ?
C12 C13 C14 C13 -0.8(4) . . . 7_575 ?
B1 O1 C2 C1 180.000(0) . . . . ?
B1 O1 C2 C3 0.000(0) . . . . ?
B1 O2 C4 C3 0.000(0) . . . . ?
B1 O2 C4 C5 180.000(0) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
