# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_jjh0925
_database_code_depnum_ccdc_archive 'CCDC 2004086'
loop_
_audit_author_name
_audit_author_address
BN
;Jiujiang University
China
;
_audit_update_record             
;
2020-05-15 deposited with the CCDC.	2020-08-29 downloaded from the CCDC.
;
_audit_creation_date             2018-09-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 B N'
_chemical_formula_sum            'C20 H14 B N'
_chemical_formula_weight         279.13
_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 0.0181 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'
N N 0.0311 0.0180 '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      monoclinic
_space_group_IT_number           15
_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                   20.7768(7)
_cell_length_b                   5.8224(2)
_cell_length_c                   24.2057(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.115(4)
_cell_angle_gamma                90
_cell_volume                     2749.58(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3033
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.5130
_cell_measurement_theta_min      4.2320
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.917
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            4684
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.534
_diffrn_reflns_theta_min         3.890
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  33.00   1.00    1.00    --  -40.98  38.00  90.00   27
  2  ω    -66.00  33.00   1.00    1.00    --  -40.98  38.00   0.00   99
  3  ω    -66.00 -24.00   1.00    1.00    --  -40.98  38.00  90.00   42
  4  ω     32.00 111.00   1.00    1.00    --   40.98  38.00-120.00   79
  5  ω     90.00 176.00   1.00    1.00    --  106.95  45.00 -60.00   86
  6  ω     68.00  95.00   1.00    1.00    --   40.98-128.00-171.00   27
  7  ω     42.00 104.00   1.00    1.00    --  106.95 -95.00-180.00   62
  8  ω     35.00 135.00   1.00    1.00    --  106.95 -77.00  30.00  100
  9  ω     30.00 150.00   1.00    1.00    --  106.95 -15.00 120.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0718621000
_diffrn_orient_matrix_UB_12      0.0057339000
_diffrn_orient_matrix_UB_13      0.0475540000
_diffrn_orient_matrix_UB_21      -0.0327230000
_diffrn_orient_matrix_UB_22      0.0138223000
_diffrn_orient_matrix_UB_23      0.0481703000
_diffrn_orient_matrix_UB_31      -0.0001877000
_diffrn_orient_matrix_UB_32      -0.2641655000
_diffrn_orient_matrix_UB_33      0.0035567000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2413
_reflns_number_total             2652
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2652
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0616
_refine_ls_restrained_S_all      1.069
_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)+(0.0914P)²+5.3845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.1792
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(B1)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C5(H5), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C20(H20), C17(H17), C2(H2), C18(H18), C3(H3), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.39027(8) 0.5772(3) 0.20850(7) 0.0207(3) Uani 1 1 d . . . . .
H1 H 0.409903 0.697364 0.200987 0.025 Uiso 1 1 calc R . . . .
C7 C 0.32222(9) 0.1890(3) 0.23030(7) 0.0148(4) Uani 1 1 d . . . . .
H7 H 0.298441 0.061480 0.236233 0.018 Uiso 1 1 calc R . . . .
C15 C 0.43088(9) 0.6421(3) 0.37427(8) 0.0199(4) Uani 1 1 d . . . . .
C6 C 0.35959(9) 0.4216(3) 0.16276(8) 0.0185(4) Uani 1 1 d . . . . .
C14 C 0.39099(9) 0.4461(3) 0.38510(8) 0.0195(4) Uani 1 1 d . . . . .
C16 C 0.42844(9) 0.7011(3) 0.31679(8) 0.0201(4) Uani 1 1 d . . . . .
C5 C 0.36310(9) 0.4559(3) 0.10620(8) 0.0205(4) Uani 1 1 d . . . . .
H5 H 0.384785 0.585687 0.098600 0.025 Uiso 1 1 calc R . . . .
C4 C 0.33453(9) 0.2978(4) 0.06206(8) 0.0217(4) Uani 1 1 d . . . . .
H4 H 0.337099 0.321301 0.024869 0.026 Uiso 1 1 calc R . . . .
C10 C 0.31804(10) 0.1101(3) 0.35309(8) 0.0215(4) Uani 1 1 d . . . . .
H10 H 0.293507 0.010550 0.323236 0.026 Uiso 1 1 calc R . . . .
C9 C 0.35290(9) 0.2952(3) 0.33912(8) 0.0193(4) Uani 1 1 d . . . . .
C11 C 0.31884(10) 0.0705(4) 0.40967(8) 0.0235(4) Uani 1 1 d . . . . .
H11 H 0.295587 -0.054274 0.417781 0.028 Uiso 1 1 calc R . . . .
C1 C 0.32599(9) 0.2253(3) 0.17381(8) 0.0182(4) Uani 1 1 d . . . . .
C12 C 0.35507(10) 0.2207(4) 0.45424(8) 0.0242(5) Uani 1 1 d . . . . .
H12 H 0.355709 0.197473 0.492433 0.029 Uiso 1 1 calc R . . . .
C13 C 0.39001(10) 0.4037(4) 0.44196(8) 0.0231(4) Uani 1 1 d . . . . .
H13 H 0.413749 0.502439 0.472330 0.028 Uiso 1 1 calc R . . . .
C20 C 0.47232(10) 0.7786(4) 0.42129(8) 0.0234(4) Uani 1 1 d . . . . .
H20 H 0.475755 0.740462 0.459505 0.028 Uiso 1 1 calc R . . . .
C17 C 0.46364(10) 0.8971(4) 0.30920(8) 0.0230(4) Uani 1 1 d . . . . .
H17 H 0.460296 0.939307 0.271255 0.028 Uiso 1 1 calc R . . . .
C2 C 0.29759(10) 0.0663(3) 0.12799(8) 0.0206(4) Uani 1 1 d . . . . .
H2 H 0.275809 -0.064465 0.134907 0.025 Uiso 1 1 calc R . . . .
C18 C 0.50297(10) 1.0297(4) 0.35564(9) 0.0252(5) Uani 1 1 d . . . . .
H18 H 0.525809 1.158794 0.349244 0.030 Uiso 1 1 calc R . . . .
C3 C 0.30171(10) 0.1024(3) 0.07312(8) 0.0217(4) Uani 1 1 d . . . . .
H3 H 0.282581 -0.003716 0.043241 0.026 Uiso 1 1 calc R . . . .
C19 C 0.50780(10) 0.9663(4) 0.41235(9) 0.0253(5) Uani 1 1 d . . . . .
H19 H 0.535132 1.051164 0.444377 0.030 Uiso 1 1 calc R . . . .
C8 C 0.35260(9) 0.3361(3) 0.27759(8) 0.0214(4) Uani 1 1 d . . . . .
B1 B 0.39032(11) 0.5455(4) 0.26594(9) 0.0207(3) 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
N1 C6 1.403(2) . ?
N1 B1 1.402(3) . ?
C7 C1 1.412(2) . ?
C7 C8 1.395(3) . ?
C15 C14 1.486(3) . ?
C15 C16 1.417(2) . ?
C15 C20 1.412(3) . ?
C6 C5 1.410(2) . ?
C6 C1 1.412(3) . ?
C14 C9 1.425(3) . ?
C14 C13 1.405(2) . ?
C16 C17 1.401(3) . ?
C16 B1 1.514(3) . ?
C5 C4 1.380(3) . ?
C4 C3 1.399(3) . ?
C10 C9 1.403(3) . ?
C10 C11 1.383(3) . ?
C9 C8 1.506(2) . ?
C11 C12 1.392(3) . ?
C1 C2 1.409(3) . ?
C12 C13 1.378(3) . ?
C20 C19 1.376(3) . ?
C17 C18 1.377(3) . ?
C2 C3 1.376(3) . ?
C18 C19 1.391(3) . ?
C8 B1 1.527(3) . ?

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
B1 N1 C6 122.86(17) . . ?
C8 C7 C1 122.88(17) . . ?
C16 C15 C14 121.70(17) . . ?
C20 C15 C14 120.85(17) . . ?
C20 C15 C16 117.44(18) . . ?
N1 C6 C5 120.92(17) . . ?
N1 C6 C1 119.57(16) . . ?
C5 C6 C1 119.50(17) . . ?
C9 C14 C15 121.98(16) . . ?
C13 C14 C15 120.31(17) . . ?
C13 C14 C9 117.72(18) . . ?
C15 C16 B1 119.03(18) . . ?
C17 C16 C15 118.82(17) . . ?
C17 C16 B1 122.10(17) . . ?
C4 C5 C6 120.35(18) . . ?
C5 C4 C3 120.16(17) . . ?
C11 C10 C9 122.37(18) . . ?
C14 C9 C8 119.14(17) . . ?
C10 C9 C14 118.65(16) . . ?
C10 C9 C8 122.20(17) . . ?
C10 C11 C12 118.80(19) . . ?
C6 C1 C7 120.00(17) . . ?
C2 C1 C7 121.10(17) . . ?
C2 C1 C6 118.90(16) . . ?
C13 C12 C11 120.23(17) . . ?
C12 C13 C14 122.23(18) . . ?
C19 C20 C15 122.10(18) . . ?
C18 C17 C16 122.65(18) . . ?
C3 C2 C1 120.76(18) . . ?
C17 C18 C19 118.55(19) . . ?
C2 C3 C4 120.33(17) . . ?
C20 C19 C18 120.32(18) . . ?
C7 C8 C9 124.15(18) . . ?
C7 C8 B1 117.05(17) . . ?
C9 C8 B1 118.75(17) . . ?
N1 B1 C16 123.29(18) . . ?
N1 B1 C8 117.58(18) . . ?
C16 B1 C8 119.06(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.593
_oxdiff_exptl_absorpt_empirical_full_min 0.597
