# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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 1967674'
loop_
_audit_author_name
_audit_author_address
Meng
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2019-11-23 deposited with the CCDC.	2020-04-17 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         ?
_chemical_formula_sum            'C26 H25 B N4 O2'
_chemical_formula_weight         436.31

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'

_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                   10.2786(4)
_cell_length_b                   12.3930(5)
_cell_length_c                   17.3660(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.5770(10)
_cell_angle_gamma                90
_cell_volume                     2209.89(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    8364
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.58

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   0.975
_exptl_transmission_factor_max   0.983
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.084
_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      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28172
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.259
_diffrn_reflns_theta_max         27.572
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5095
_reflns_number_gt                3702
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1251P)²+0.0058P] 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         5095
_refine_ls_number_parameters     298
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.2008
_refine_ls_wR_factor_gt          0.1798
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.167
_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
O1 O 0.16083(13) 0.31567(10) 0.49425(8) 0.0394(4) Uani 1 1 d . . . . .
N3 N 0.51085(13) 0.74889(11) 0.46335(8) 0.0241(3) Uani 1 1 d . . . . .
N4 N 0.37104(13) 0.80186(11) 0.54425(8) 0.0255(3) Uani 1 1 d . . . . .
N2 N 0.44037(14) 0.89189(11) 0.52792(8) 0.0286(4) Uani 1 1 d . . . . .
O2 O 0.36218(16) 0.15746(12) 0.72187(9) 0.0564(5) Uani 1 1 d . . . . .
C21 C 0.41140(15) 0.71661(13) 0.50592(9) 0.0230(4) Uani 1 1 d . . . . .
C22 C 0.52303(16) 0.85635(13) 0.47900(10) 0.0263(4) Uani 1 1 d . . . . .
H22A H 0.585859 0.901161 0.456394 0.032 Uiso 1 1 calc R U . . .
C3 C 0.34710(15) 0.61016(13) 0.50686(9) 0.0226(4) Uani 1 1 d . . . . .
C8 C 0.27300(17) 0.23914(14) 0.60555(10) 0.0324(4) Uani 1 1 d . . . . .
C7 C 0.16861(19) 0.23927(15) 0.55184(11) 0.0355(5) Uani 1 1 d . . . . .
C13 C 0.47228(18) 0.32337(15) 0.67977(10) 0.0320(4) Uani 1 1 d . . . . .
C2 C 0.39528(15) 0.52643(13) 0.55328(9) 0.0234(4) Uani 1 1 d . . . . .
H2B H 0.468603 0.540053 0.587140 0.028 Uiso 1 1 calc R U . . .
C1 C 0.34049(15) 0.42299(13) 0.55229(9) 0.0237(4) Uani 1 1 d . . . . .
C6 C 0.22873(17) 0.41169(14) 0.50364(10) 0.0285(4) Uani 1 1 d . . . . .
C18 C 0.56178(19) 0.40259(16) 0.70288(10) 0.0350(5) Uani 1 1 d . . . . .
H18A H 0.580724 0.457494 0.666891 0.042 Uiso 1 1 calc R U . . .
C23 C 0.27713(17) 0.80740(15) 0.60593(11) 0.0351(5) Uani 1 1 d . . . . .
H23A H 0.241114 0.734635 0.614950 0.042 Uiso 1 1 calc R U . . .
H23B H 0.204105 0.855578 0.589705 0.042 Uiso 1 1 calc R U . . .
C14 C 0.4489(2) 0.24291(17) 0.73434(11) 0.0420(5) Uani 1 1 d . . . . .
C4 C 0.23610(18) 0.59408(15) 0.46002(10) 0.0323(4) Uani 1 1 d . . . . .
H4A H 0.201843 0.651159 0.428724 0.039 Uiso 1 1 calc R U . . .
C5 C 0.17608(18) 0.49545(16) 0.45910(11) 0.0356(5) Uani 1 1 d . . . . .
H5A H 0.098708 0.484307 0.428124 0.043 Uiso 1 1 calc R U . . .
N1 N 0.7101(2) 0.4897(2) 0.79565(11) 0.0645(6) Uani 1 1 d . . . . .
C16 C 0.6001(2) 0.3223(2) 0.82713(12) 0.0562(7) Uani 1 1 d . . . . .
H16A H 0.643054 0.320712 0.876707 0.067 Uiso 1 1 calc R U . . .
C9 C 0.2678(2) 0.16277(16) 0.66404(12) 0.0426(5) Uani 1 1 d . . . . .
C12 C 0.0688(2) 0.16403(17) 0.55095(14) 0.0482(6) Uani 1 1 d . . . . .
H12A H 0.001072 0.164880 0.511873 0.058 Uiso 1 1 calc R U . . .
C15 C 0.5133(2) 0.2425(2) 0.80589(12) 0.0561(7) Uani 1 1 d . . . . .
H15A H 0.497211 0.185849 0.841050 0.067 Uiso 1 1 calc R U . . .
C17 C 0.6255(2) 0.40657(19) 0.77558(11) 0.0442(6) Uani 1 1 d . . . . .
C11 C 0.0715(3) 0.08766(18) 0.60910(16) 0.0575(7) Uani 1 1 d . . . . .
H11A H 0.004926 0.034462 0.609237 0.069 Uiso 1 1 calc R U . . .
C10 C 0.1670(3) 0.08660(17) 0.66628(15) 0.0563(7) Uani 1 1 d . . . . .
H10A H 0.165368 0.035241 0.706837 0.068 Uiso 1 1 calc R U . . .
B1 B 0.3948(2) 0.31649(16) 0.59722(11) 0.0283(4) Uani 1 1 d . . . . .
C24 C 0.34222(19) 0.8495(2) 0.67986(11) 0.0515(6) Uani 1 1 d D U . . .
H24A H 0.278049 0.847284 0.720664 0.062 Uiso 1 1 calc R U . . .
H24B H 0.365597 0.926096 0.671987 0.062 Uiso 1 1 calc R U . . .
C25 C 0.4643(2) 0.7892(2) 0.70886(13) 0.0644(7) Uani 1 1 d D U . . .
H25A H 0.441951 0.713042 0.719432 0.077 Uiso 1 1 calc R U . . .
H25B H 0.529438 0.789947 0.668576 0.077 Uiso 1 1 calc R U . . .
C20 C 0.7228(3) 0.5791(3) 0.74671(15) 0.0745(9) Uani 1 1 d . . . . .
H20A H 0.786507 0.629645 0.769942 0.112 Uiso 1 1 calc R U . . .
H20B H 0.752398 0.554710 0.696745 0.112 Uiso 1 1 calc R U . . .
H20C H 0.638345 0.615196 0.739330 0.112 Uiso 1 1 calc R U . . .
C26 C 0.5221(3) 0.8410(3) 0.78183(14) 0.0934(12) Uani 1 1 d . . . . .
H26A H 0.600241 0.801191 0.799527 0.140 Uiso 1 1 calc R U . . .
H26B H 0.545404 0.916029 0.771146 0.140 Uiso 1 1 calc R U . . .
H26C H 0.458042 0.839234 0.821929 0.140 Uiso 1 1 calc R U . . .
C19 C 0.7793(3) 0.4918(3) 0.86951(15) 0.0966(13) Uani 1 1 d . . . . .
H19A H 0.834217 0.556437 0.873212 0.145 Uiso 1 1 calc R U . . .
H19B H 0.716800 0.493128 0.910473 0.145 Uiso 1 1 calc R U . . .
H19C H 0.834113 0.427334 0.875174 0.145 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 C7 1.377(2) . ?
O1 C6 1.385(2) . ?
N3 C21 1.349(2) . ?
N3 C22 1.364(2) . ?
N3 B1 1.672(2) 3_666 ?
N4 C21 1.325(2) . ?
N4 N2 1.3606(19) . ?
N4 C23 1.475(2) . ?
N2 C22 1.305(2) . ?
O2 C9 1.366(3) . ?
O2 C14 1.395(3) . ?
C21 C3 1.476(2) . ?
C22 H22A 0.9500 . ?
C3 C4 1.386(2) . ?
C3 C2 1.391(2) . ?
C8 C7 1.390(3) . ?
C8 C9 1.391(3) . ?
C8 B1 1.588(3) . ?
C7 C12 1.386(3) . ?
C13 C18 1.392(3) . ?
C13 C14 1.404(3) . ?
C13 B1 1.611(3) . ?
C2 C1 1.400(2) . ?
C2 H2B 0.9500 . ?
C1 C6 1.402(2) . ?
C1 B1 1.620(3) . ?
C6 C5 1.390(3) . ?
C18 C17 1.397(3) . ?
C18 H18A 0.9500 . ?
C23 C24 1.514(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C14 C15 1.381(3) . ?
C4 C5 1.369(3) . ?
C4 H4A 0.9500 . ?
C5 H5A 0.9500 . ?
N1 C17 1.383(3) . ?
N1 C20 1.406(4) . ?
N1 C19 1.439(3) . ?
C16 C15 1.371(4) . ?
C16 C17 1.408(4) . ?
C16 H16A 0.9500 . ?
C9 C10 1.403(3) . ?
C12 C11 1.383(3) . ?
C12 H12A 0.9500 . ?
C15 H15A 0.9500 . ?
C11 C10 1.365(4) . ?
C11 H11A 0.9500 . ?
C10 H10A 0.9500 . ?
C24 C25 1.5267(10) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.518(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C7 O1 C6 119.52(14) . . ?
C21 N3 C22 104.20(14) . . ?
C21 N3 B1 132.56(13) . 3_666 ?
C22 N3 B1 123.23(13) . 3_666 ?
C21 N4 N2 111.74(13) . . ?
C21 N4 C23 129.17(14) . . ?
N2 N4 C23 118.62(13) . . ?
C22 N2 N4 102.78(13) . . ?
C9 O2 C14 120.34(15) . . ?
N4 C21 N3 107.51(14) . . ?
N4 C21 C3 123.82(14) . . ?
N3 C21 C3 128.46(14) . . ?
N2 C22 N3 113.76(15) . . ?
N2 C22 H22A 123.1 . . ?
N3 C22 H22A 123.1 . . ?
C4 C3 C2 119.68(15) . . ?
C4 C3 C21 118.65(15) . . ?
C2 C3 C21 121.68(14) . . ?
C7 C8 C9 115.91(17) . . ?
C7 C8 B1 121.74(16) . . ?
C9 C8 B1 122.24(18) . . ?
O1 C7 C12 115.83(19) . . ?
O1 C7 C8 120.41(15) . . ?
C12 C7 C8 123.75(19) . . ?
C18 C13 C14 115.93(18) . . ?
C18 C13 B1 126.01(16) . . ?
C14 C13 B1 118.06(18) . . ?
C3 C2 C1 122.91(15) . . ?
C3 C2 H2B 118.5 . . ?
C1 C2 H2B 118.5 . . ?
C2 C1 C6 114.65(15) . . ?
C2 C1 B1 127.63(14) . . ?
C6 C1 B1 117.66(15) . . ?
O1 C6 C5 113.24(15) . . ?
O1 C6 C1 123.46(16) . . ?
C5 C6 C1 123.29(16) . . ?
C13 C18 C17 124.23(19) . . ?
C13 C18 H18A 117.9 . . ?
C17 C18 H18A 117.9 . . ?
N4 C23 C24 110.68(15) . . ?
N4 C23 H23A 109.5 . . ?
C24 C23 H23A 109.5 . . ?
N4 C23 H23B 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
C15 C14 O2 114.46(19) . . ?
C15 C14 C13 121.3(2) . . ?
O2 C14 C13 124.20(19) . . ?
C5 C4 C3 119.60(17) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 C6 119.77(16) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C17 N1 C20 120.60(18) . . ?
C17 N1 C19 121.2(3) . . ?
C20 N1 C19 118.0(2) . . ?
C15 C16 C17 120.1(2) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?
O2 C9 C8 121.35(18) . . ?
O2 C9 C10 116.60(19) . . ?
C8 C9 C10 122.1(2) . . ?
C11 C12 C7 117.5(2) . . ?
C11 C12 H12A 121.3 . . ?
C7 C12 H12A 121.3 . . ?
C16 C15 C14 121.3(2) . . ?
C16 C15 H15A 119.4 . . ?
C14 C15 H15A 119.4 . . ?
N1 C17 C18 121.2(2) . . ?
N1 C17 C16 121.7(2) . . ?
C18 C17 C16 117.1(2) . . ?
C10 C11 C12 121.8(2) . . ?
C10 C11 H11A 119.1 . . ?
C12 C11 H11A 119.1 . . ?
C11 C10 C9 118.8(2) . . ?
C11 C10 H10A 120.6 . . ?
C9 C10 H10A 120.6 . . ?
C8 B1 C13 108.13(15) . . ?
C8 B1 C1 106.25(15) . . ?
C13 B1 C1 122.11(15) . . ?
C8 B1 N3 104.28(13) . 3_666 ?
C13 B1 N3 107.94(14) . 3_666 ?
C1 B1 N3 106.80(13) . 3_666 ?
C23 C24 C25 115.87(18) . . ?
C23 C24 H24A 108.3 . . ?
C25 C24 H24A 108.3 . . ?
C23 C24 H24B 108.3 . . ?
C25 C24 H24B 108.3 . . ?
H24A C24 H24B 107.4 . . ?
C26 C25 C24 110.7(2) . . ?
C26 C25 H25A 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.887
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.053

