# Electronic Supplementary Material (ESI) for ChemComm.
# 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_kitamoto20170112
_database_code_depnum_ccdc_archive 'CCDC 1570941'
_audit_update_record             
;
2017-08-26 deposited with the CCDC.	2021-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H14 B N O2'
_chemical_formula_weight         359.17

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'
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   10.9490(12)
_cell_length_b                   19.966(2)
_cell_length_c                   7.4024(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.4220(10)
_cell_angle_gamma                90.00
_cell_volume                     1596.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2741
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      27.88

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6375
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4595
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         27.89
_reflns_number_total             1866
_reflns_number_gt                1677
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEXII'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0759P)²+0.9757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1866
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.014

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0000 0.47634(7) 0.2500 0.0144(3) Uani 1 2 d S . .
O1 O 0.20581(6) 0.47877(4) 0.17059(10) 0.0159(2) Uani 1 1 d . . .
C3 C 0.10987(9) 0.58630(5) 0.21198(13) 0.0138(3) Uani 1 1 d . . .
B1 B 0.0000 0.55006(8) 0.2500 0.0148(3) Uani 1 2 d S . .
C5 C 0.10393(9) 0.44285(5) 0.21026(13) 0.0146(2) Uani 1 1 d . . .
C6 C 0.20933(9) 0.54861(5) 0.17094(13) 0.0140(2) Uani 1 1 d . . .
N1 N 0.0000 0.68965(6) 0.2500 0.0133(3) Uani 1 2 d S . .
C8 C 0.10766(9) 0.65663(5) 0.21134(13) 0.0130(2) Uani 1 1 d . . .
C9 C 0.0000 0.76168(7) 0.2500 0.0136(3) Uani 1 2 d S . .
C10 C 0.21235(9) 0.68981(5) 0.16783(13) 0.0148(2) Uani 1 1 d . . .
H1 H 0.2160 0.7363 0.1660 0.018 Uiso 1 1 calc R . .
C13 C 0.10537(9) 0.37337(5) 0.20953(14) 0.0166(3) Uani 1 1 d . . .
H2 H 0.1734 0.3496 0.1833 0.020 Uiso 1 1 calc R . .
C15 C 0.31275(9) 0.58096(5) 0.12726(14) 0.0162(2) Uani 1 1 d . . .
H3 H 0.3802 0.5572 0.0992 0.019 Uiso 1 1 calc R . .
C17 C 0.31085(9) 0.65106(5) 0.12731(15) 0.0162(2) Uani 1 1 d . . .
H4 H 0.3797 0.6734 0.0985 0.019 Uiso 1 1 calc R . .
C19 C 0.0000 0.34063(7) 0.2500 0.0179(3) Uani 1 2 d S . .
H5 H 0.0000 0.2941 0.2500 0.021 Uiso 1 2 calc SR . .
C20 C -0.07599(10) 0.86612(5) 0.11263(15) 0.0185(3) Uani 1 1 d . . .
H6 H -0.1276 0.8895 0.0219 0.022 Uiso 1 1 calc R . .
C21 C -0.07488(9) 0.79630(5) 0.11069(14) 0.0158(2) Uani 1 1 d . . .
H7 H -0.1239 0.7730 0.0168 0.019 Uiso 1 1 calc R . .
C22 C 0.0000 0.90061(7) 0.2500 0.0200(3) Uani 1 2 d S . .
H8 H 0.0000 0.9472 0.2500 0.024 Uiso 1 2 calc SR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0148(7) 0.0136(7) 0.0151(7) 0.000 0.0032(5) 0.000
O1 0.0138(4) 0.0133(4) 0.0218(5) 0.0003(3) 0.0064(3) 0.0012(3)
C3 0.0139(5) 0.0137(5) 0.0142(5) -0.0001(3) 0.0035(4) 0.0008(3)
B1 0.0150(8) 0.0144(8) 0.0154(8) 0.000 0.0036(6) 0.000
C5 0.0139(5) 0.0158(5) 0.0144(5) 0.0004(3) 0.0027(4) -0.0007(3)
C6 0.0144(5) 0.0135(5) 0.0139(5) 0.0003(3) 0.0019(4) 0.0008(3)
N1 0.0120(6) 0.0116(6) 0.0169(6) 0.000 0.0045(5) 0.000
C8 0.0120(5) 0.0147(5) 0.0126(5) 0.0001(3) 0.0031(4) 0.0009(3)
C9 0.0127(6) 0.0127(6) 0.0171(7) 0.000 0.0071(5) 0.000
C10 0.0151(5) 0.0137(5) 0.0160(5) 0.0006(4) 0.0036(4) -0.0010(4)
C13 0.0175(5) 0.0146(5) 0.0177(6) -0.0002(4) 0.0027(4) 0.0028(4)
C15 0.0128(5) 0.0191(5) 0.0176(5) 0.0004(4) 0.0051(4) 0.0024(4)
C17 0.0128(5) 0.0193(5) 0.0173(5) 0.0017(4) 0.0047(4) -0.0020(4)
C19 0.0219(7) 0.0115(6) 0.0199(7) 0.000 0.0025(6) 0.000
C20 0.0178(5) 0.0176(5) 0.0221(6) 0.0048(4) 0.0086(4) 0.0043(4)
C21 0.0138(5) 0.0176(5) 0.0168(5) -0.0002(4) 0.0053(4) -0.0003(3)
C22 0.0229(7) 0.0137(6) 0.0267(8) 0.000 0.0138(6) 0.000

_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
C1 C5 1.3922(12) . ?
C1 C5 1.3922(12) 2 ?
C1 B1 1.472(2) . ?
O1 C6 1.3951(12) . ?
O1 C5 1.3971(12) . ?
C3 C6 1.3974(13) . ?
C3 C8 1.4045(14) . ?
C3 B1 1.4699(13) . ?
B1 C3 1.4699(13) 2 ?
C5 C13 1.3875(15) . ?
C6 C15 1.3870(13) . ?
N1 C8 1.4200(11) 2 ?
N1 C8 1.4200(11) . ?
N1 C9 1.4382(17) . ?
C8 C10 1.4062(13) . ?
C9 C21 1.3916(12) 2 ?
C9 C21 1.3916(12) . ?
C10 C17 1.3991(14) . ?
C10 H1 0.9300 . ?
C13 C19 1.4004(12) . ?
C13 H2 0.9300 . ?
C15 C17 1.3997(14) . ?
C15 H3 0.9300 . ?
C17 H4 0.9300 . ?
C19 C13 1.4003(12) 2 ?
C19 H5 0.9300 . ?
C20 C22 1.3869(13) . ?
C20 C21 1.3943(14) . ?
C20 H6 0.9300 . ?
C21 H7 0.9300 . ?
C22 C20 1.3869(13) 2 ?
C22 H8 0.9300 . ?

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
C5 C1 C5 122.59(13) . 2 ?
C5 C1 B1 118.70(7) . . ?
C5 C1 B1 118.70(7) 2 . ?
C6 O1 C5 122.38(7) . . ?
C6 C3 C8 123.45(9) . . ?
C6 C3 B1 117.90(10) . . ?
C8 C3 B1 118.59(10) . . ?
C3 B1 C3 121.03(14) 2 . ?
C3 B1 C1 119.49(7) 2 . ?
C3 B1 C1 119.48(7) . . ?
C13 C5 C1 119.42(9) . . ?
C13 C5 O1 120.16(9) . . ?
C1 C5 O1 120.41(10) . . ?
C15 C6 O1 119.24(8) . . ?
C15 C6 C3 119.66(10) . . ?
O1 C6 C3 121.09(9) . . ?
C8 N1 C8 124.68(12) 2 . ?
C8 N1 C9 117.66(6) 2 . ?
C8 N1 C9 117.66(6) . . ?
C3 C8 C10 117.23(9) . . ?
C3 C8 N1 118.55(9) . . ?
C10 C8 N1 124.21(10) . . ?
C21 C9 C21 120.44(13) 2 . ?
C21 C9 N1 119.78(6) 2 . ?
C21 C9 N1 119.78(6) . . ?
C17 C10 C8 118.33(10) . . ?
C17 C10 H1 120.8 . . ?
C8 C10 H1 120.8 . . ?
C5 C13 C19 117.10(9) . . ?
C5 C13 H2 121.4 . . ?
C19 C13 H2 121.5 . . ?
C6 C15 C17 116.93(9) . . ?
C6 C15 H3 121.5 . . ?
C17 C15 H3 121.5 . . ?
C10 C17 C15 124.40(9) . . ?
C10 C17 H4 117.8 . . ?
C15 C17 H4 117.8 . . ?
C13 C19 C13 124.36(13) 2 . ?
C13 C19 H5 117.8 2 . ?
C13 C19 H5 117.8 . . ?
C22 C20 C21 119.92(10) . . ?
C22 C20 H6 120.0 . . ?
C21 C20 H6 120.0 . . ?
C9 C21 C20 119.61(10) . . ?
C9 C21 H7 120.2 . . ?
C20 C21 H7 120.2 . . ?
C20 C22 C20 120.46(13) . 2 ?
C20 C22 H8 119.8 . . ?
C20 C22 H8 119.8 2 . ?

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
C6 C3 B1 C3 -177.89(9) . . . 2 ?
C8 C3 B1 C3 -0.45(6) . . . 2 ?
C6 C3 B1 C1 2.11(9) . . . . ?
C8 C3 B1 C1 179.55(6) . . . . ?
C5 C1 B1 C3 178.78(6) . . . 2 ?
C5 C1 B1 C3 -1.22(6) 2 . . 2 ?
C5 C1 B1 C3 -1.22(6) . . . . ?
C5 C1 B1 C3 178.78(6) 2 . . . ?
C5 C1 C5 C13 0.06(6) 2 . . . ?
B1 C1 C5 C13 -179.94(6) . . . . ?
C5 C1 C5 O1 179.77(10) 2 . . . ?
B1 C1 C5 O1 -0.23(10) . . . . ?
C6 O1 C5 C13 -179.48(8) . . . . ?
C6 O1 C5 C1 0.81(12) . . . . ?
C5 O1 C6 C15 -178.94(8) . . . . ?
C5 O1 C6 C3 0.15(13) . . . . ?
C8 C3 C6 C15 0.19(15) . . . . ?
B1 C3 C6 C15 177.50(8) . . . . ?
C8 C3 C6 O1 -178.90(9) . . . . ?
B1 C3 C6 O1 -1.59(13) . . . . ?
C6 C3 C8 C10 -0.41(14) . . . . ?
B1 C3 C8 C10 -177.70(7) . . . . ?
C6 C3 C8 N1 178.17(8) . . . . ?
B1 C3 C8 N1 0.88(12) . . . . ?
C8 N1 C8 C3 -0.46(6) 2 . . . ?
C9 N1 C8 C3 179.54(6) . . . . ?
C8 N1 C8 C10 178.01(10) 2 . . . ?
C9 N1 C8 C10 -1.99(10) . . . . ?
C8 N1 C9 C21 109.65(6) 2 . . 2 ?
C8 N1 C9 C21 -70.35(6) . . . 2 ?
C8 N1 C9 C21 -70.35(6) 2 . . . ?
C8 N1 C9 C21 109.65(6) . . . . ?
C3 C8 C10 C17 0.36(13) . . . . ?
N1 C8 C10 C17 -178.13(8) . . . . ?
C1 C5 C13 C19 -0.11(12) . . . . ?
O1 C5 C13 C19 -179.82(7) . . . . ?
O1 C6 C15 C17 179.18(8) . . . . ?
C3 C6 C15 C17 0.08(14) . . . . ?
C8 C10 C17 C15 -0.11(15) . . . . ?
C6 C15 C17 C10 -0.11(15) . . . . ?
C5 C13 C19 C13 0.06(6) . . . 2 ?
C21 C9 C21 C20 -0.94(6) 2 . . . ?
N1 C9 C21 C20 179.06(6) . . . . ?
C22 C20 C21 C9 1.88(13) . . . . ?
C21 C20 C22 C20 -0.94(6) . . . 2 ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        27.89
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.055
