# 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_huang0317
_database_code_depnum_ccdc_archive 'CCDC 2004088'
loop_
_audit_author_name
_audit_author_address
BN-NH
;Jiujiang University
China
;
_audit_update_record             
;
2020-05-15 deposited with the CCDC.	2020-08-29 downloaded from the CCDC.
;
_audit_creation_date             2019-03-18
_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         'C27 H21 B N2'
_chemical_formula_sum            'C27 H21 B N2'
_chemical_formula_weight         384.27
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   18.5896(5)
_cell_length_b                   8.4699(2)
_cell_length_c                   24.5627(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3867.45(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2789
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.9460
_cell_measurement_theta_min      3.5750
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64289
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9720
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.653
_diffrn_reflns_theta_min         3.599
_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 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00 -19.00   1.00    2.00    --  -40.98 -38.00  60.00   25
  2  ω    -66.00  22.00   1.00    2.00    --  -40.98  38.00  60.00   88
  3  ω     65.00  97.00   1.00    2.00    --   40.98-125.00   0.00   32
  4  ω     71.00 104.00   1.00    4.00    --  106.95 -95.00  60.00   33
  5  ω     36.00  67.00   1.00    4.00    --  106.95 -95.00  60.00   31
  6  ω     81.00 170.00   1.00    4.00    --  106.95  45.00  90.00   89
  7  ω    108.00 168.00   1.00    4.00    --  106.95 125.00 -90.00   60
  8  ω    114.00 176.00   1.00    4.00    --  106.95  45.00-180.00   62
  9  ω    -87.00 -62.00   1.00    2.00    --  -40.98-147.00-165.00   25
 10  ω   -114.00 -85.00   1.00    2.00    --  -40.98 -38.00  60.00   29
;
_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      0.0528707000
_diffrn_orient_matrix_UB_12      0.0056542000
_diffrn_orient_matrix_UB_13      0.0482772000
_diffrn_orient_matrix_UB_21      -0.0627163000
_diffrn_orient_matrix_UB_22      -0.0289882000
_diffrn_orient_matrix_UB_23      0.0397879000
_diffrn_orient_matrix_UB_31      0.0118002000
_diffrn_orient_matrix_UB_32      -0.1793768000
_diffrn_orient_matrix_UB_33      -0.0049067000
_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                2911
_reflns_number_total             3806
_reflns_odcompleteness_completeness 99.97
_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         0.286
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3806
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0526
_refine_ls_restrained_S_all      1.027
_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)+(0.0704P)²+1.1007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1437
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C5(H5), C14(H14), C4(H4), C11(H11), C20(H20), C17(H17),
 C2(H2A), C22(H22), C3(H3), C25(H25), C9(H9), C8(H8), C18(H18), C23(H23),
 C10(H10), C26(H26)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_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 0.60326(8) 0.03773(18) 0.48691(7) 0.0225(4) Uani 1 1 d . . . . .
H1 H 0.579132 -0.025652 0.466540 0.027 Uiso 1 1 calc R . . . .
N2 N 0.68891(9) 0.6237(2) 0.40327(7) 0.0272(4) Uani 1 1 d . . . . .
H2 H 0.732479 0.650518 0.410547 0.033 Uiso 1 1 calc R . . . .
C1 C 0.67001(10) 0.0728(2) 0.63436(8) 0.0209(4) Uani 1 1 d . . . . .
C13 C 0.66138(10) 0.1074(2) 0.57607(8) 0.0206(4) Uani 1 1 d . . . . .
C6 C 0.64694(10) -0.0741(2) 0.65586(8) 0.0210(4) Uani 1 1 d . . . . .
C12 C 0.60041(10) -0.1738(2) 0.56516(8) 0.0217(4) Uani 1 1 d . . . . .
C16 C 0.62477(10) 0.1810(2) 0.46529(8) 0.0209(4) Uani 1 1 d . . . . .
C15 C 0.66979(10) 0.2811(2) 0.49645(8) 0.0211(4) Uani 1 1 d . . . . .
C7 C 0.61826(10) -0.2021(2) 0.62029(8) 0.0221(4) Uani 1 1 d . . . . .
C5 C 0.65125(10) -0.0974(2) 0.71239(8) 0.0240(4) Uani 1 1 d . . . . .
H5 H 0.635028 -0.192196 0.727014 0.029 Uiso 1 1 calc R . . . .
C14 C 0.68781(10) 0.2403(2) 0.55141(8) 0.0213(4) Uani 1 1 d . . . . .
H14 H 0.718418 0.306125 0.570940 0.026 Uiso 1 1 calc R . . . .
C19 C 0.66616(10) 0.4779(2) 0.42406(8) 0.0233(4) Uani 1 1 d . . . . .
C4 C 0.67878(10) 0.0161(2) 0.74692(8) 0.0242(4) Uani 1 1 d . . . . .
H4 H 0.681366 -0.002924 0.784160 0.029 Uiso 1 1 calc R . . . .
C21 C 0.64912(10) 0.7304(2) 0.37212(8) 0.0223(4) Uani 1 1 d . . . . .
C11 C 0.57226(10) -0.2980(2) 0.53409(8) 0.0243(4) Uani 1 1 d . . . . .
H11 H 0.559505 -0.279543 0.498036 0.029 Uiso 1 1 calc R . . . .
C20 C 0.69033(10) 0.4281(2) 0.47430(8) 0.0226(4) Uani 1 1 d . . . . .
H20 H 0.720993 0.493090 0.494111 0.027 Uiso 1 1 calc R . . . .
C17 C 0.60145(10) 0.2314(2) 0.41367(8) 0.0241(4) Uani 1 1 d . . . . .
H17 H 0.572237 0.165720 0.392874 0.029 Uiso 1 1 calc R . . . .
C2 C 0.69762(10) 0.1866(2) 0.67062(8) 0.0236(4) Uani 1 1 d . . . . .
H2A H 0.712904 0.283381 0.656949 0.028 Uiso 1 1 calc R . . . .
C22 C 0.68563(10) 0.8476(2) 0.34379(8) 0.0238(4) Uani 1 1 d . . . . .
H22 H 0.735485 0.853341 0.346235 0.029 Uiso 1 1 calc R . . . .
C3 C 0.70259(10) 0.1587(2) 0.72572(8) 0.0247(4) Uani 1 1 d . . . . .
H3 H 0.721856 0.235124 0.748655 0.030 Uiso 1 1 calc R . . . .
C25 C 0.53800(11) 0.8346(2) 0.33535(8) 0.0263(4) Uani 1 1 d . . . . .
H25 H 0.488139 0.829280 0.332827 0.032 Uiso 1 1 calc R . . . .
C9 C 0.58300(11) -0.4759(2) 0.60912(9) 0.0268(4) Uani 1 1 d . . . . .
H9 H 0.578166 -0.576907 0.623510 0.032 Uiso 1 1 calc R . . . .
C8 C 0.60995(10) -0.3563(2) 0.64112(9) 0.0257(4) Uani 1 1 d . . . . .
H8 H 0.622868 -0.377434 0.676968 0.031 Uiso 1 1 calc R . . . .
C18 C 0.62128(11) 0.3763(2) 0.39357(8) 0.0247(4) Uani 1 1 d . . . . .
H18 H 0.604973 0.407976 0.359478 0.030 Uiso 1 1 calc R . . . .
C23 C 0.64899(11) 0.9559(2) 0.31199(8) 0.0251(4) Uani 1 1 d . . . . .
H23 H 0.674685 1.034313 0.293978 0.030 Uiso 1 1 calc R . . . .
C10 C 0.56299(10) -0.4473(2) 0.55565(9) 0.0257(4) Uani 1 1 d . . . . .
H10 H 0.543520 -0.527710 0.534517 0.031 Uiso 1 1 calc R . . . .
C26 C 0.57388(11) 0.7262(2) 0.36818(8) 0.0258(4) Uani 1 1 d . . . . .
H26 H 0.547933 0.650952 0.387524 0.031 Uiso 1 1 calc R . . . .
C24 C 0.57418(11) 0.9500(2) 0.30636(8) 0.0244(4) Uani 1 1 d . . . . .
C27 C 0.53545(12) 1.0687(3) 0.27088(9) 0.0326(5) Uani 1 1 d . . . . .
H27A H 0.499406 1.015695 0.249695 0.049 Uiso 1 1 calc GR . . . .
H27B H 0.569360 1.118761 0.246975 0.049 Uiso 1 1 calc GR . . . .
H27C H 0.513025 1.147071 0.293454 0.049 Uiso 1 1 calc GR . . . .
B1 B 0.61901(11) -0.0099(3) 0.54100(9) 0.0216(4) 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 C16 1.383(2) . ?
N1 B1 1.419(3) . ?
N2 C19 1.401(2) . ?
N2 C21 1.396(2) . ?
C1 C13 1.470(3) . ?
C1 C6 1.418(3) . ?
C1 C2 1.410(3) . ?
C13 C14 1.369(3) . ?
C13 B1 1.533(3) . ?
C6 C7 1.490(3) . ?
C6 C5 1.405(3) . ?
C12 C7 1.415(3) . ?
C12 C11 1.401(3) . ?
C12 B1 1.549(3) . ?
C16 C15 1.416(3) . ?
C16 C17 1.406(3) . ?
C15 C14 1.433(3) . ?
C15 C20 1.412(3) . ?
C7 C8 1.412(3) . ?
C5 C4 1.380(3) . ?
C19 C20 1.379(3) . ?
C19 C18 1.414(3) . ?
C4 C3 1.388(3) . ?
C21 C22 1.389(3) . ?
C21 C26 1.402(3) . ?
C11 C10 1.381(3) . ?
C17 C18 1.374(3) . ?
C2 C3 1.377(3) . ?
C22 C23 1.384(3) . ?
C25 C26 1.392(3) . ?
C25 C24 1.384(3) . ?
C9 C8 1.377(3) . ?
C9 C10 1.386(3) . ?
C23 C24 1.399(3) . ?
C24 C27 1.513(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
C16 N1 B1 123.29(17) . . ?
C21 N2 C19 127.61(16) . . ?
C6 C1 C13 120.32(17) . . ?
C2 C1 C13 121.23(17) . . ?
C2 C1 C6 118.37(18) . . ?
C1 C13 B1 118.29(17) . . ?
C14 C13 C1 123.76(17) . . ?
C14 C13 B1 117.94(18) . . ?
C1 C6 C7 121.85(17) . . ?
C5 C6 C1 118.28(18) . . ?
C5 C6 C7 119.86(17) . . ?
C7 C12 B1 117.77(17) . . ?
C11 C12 C7 118.81(18) . . ?
C11 C12 B1 123.22(18) . . ?
N1 C16 C15 119.24(17) . . ?
N1 C16 C17 121.54(17) . . ?
C17 C16 C15 119.20(18) . . ?
C16 C15 C14 120.20(17) . . ?
C20 C15 C16 118.67(18) . . ?
C20 C15 C14 120.83(17) . . ?
C12 C7 C6 121.47(17) . . ?
C8 C7 C6 119.97(18) . . ?
C8 C7 C12 118.54(18) . . ?
C4 C5 C6 122.08(18) . . ?
C13 C14 C15 122.06(17) . . ?
N2 C19 C18 121.43(18) . . ?
C20 C19 N2 119.83(18) . . ?
C20 C19 C18 118.68(18) . . ?
C5 C4 C3 119.58(18) . . ?
N2 C21 C26 123.35(17) . . ?
C22 C21 N2 118.57(17) . . ?
C22 C21 C26 118.08(18) . . ?
C10 C11 C12 121.66(19) . . ?
C19 C20 C15 121.78(18) . . ?
C18 C17 C16 120.84(18) . . ?
C3 C2 C1 121.86(18) . . ?
C23 C22 C21 121.06(18) . . ?
C2 C3 C4 119.81(18) . . ?
C24 C25 C26 122.07(18) . . ?
C8 C9 C10 120.65(19) . . ?
C9 C8 C7 120.93(19) . . ?
C17 C18 C19 120.81(19) . . ?
C22 C23 C24 121.43(18) . . ?
C11 C10 C9 119.34(18) . . ?
C25 C26 C21 120.08(18) . . ?
C25 C24 C23 117.24(18) . . ?
C25 C24 C27 122.32(18) . . ?
C23 C24 C27 120.42(18) . . ?
N1 B1 C13 116.62(18) . . ?
N1 B1 C12 124.56(18) . . ?
C13 B1 C12 118.71(18) . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.390
_oxdiff_exptl_absorpt_empirical_full_min 0.708
