# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_ic19718
_database_code_depnum_ccdc_archive 'CCDC 2064006'
loop_
_audit_author_name
_audit_author_address
'Gene-Hsiang Lee'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-06-15 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            'C30 H43 B F2 N2 O3'
_chemical_formula_weight         528.47

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.9360(4)
_cell_length_b                   13.5817(7)
_cell_length_c                   14.9895(8)
_cell_angle_alpha                67.7447(12)
_cell_angle_beta                 79.9145(13)
_cell_angle_gamma                76.0472(12)
_cell_volume                     1444.83(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9814
_cell_measurement_theta_min      3.58
_cell_measurement_theta_max      75.05

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.184
_exptl_absorpt_coefficient_mu    0.695
_shelx_estimated_absorpt_T_min   0.779
_shelx_estimated_absorpt_T_max   0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6928
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11230
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.583
_diffrn_reflns_theta_max         74.992
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5899
_reflns_number_gt                5533
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0548P)²+0.3653P] 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         5899
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_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
B1 B 0.53849(16) 0.48602(9) 0.69756(8) 0.0284(2) Uani 1 1 d . . . . .
F1 F 0.46904(9) 0.40108(5) 0.70160(5) 0.03608(17) Uani 1 1 d . . . . .
F2 F 0.68999(9) 0.45226(5) 0.74133(5) 0.03825(17) Uani 1 1 d . . . . .
N1 N 0.56865(11) 0.56633(7) 0.58778(6) 0.02524(18) Uani 1 1 d . . . . .
N2 N 0.46491(11) 0.66909(7) 0.57866(6) 0.02842(19) Uani 1 1 d . . . . .
O1 O 0.41011(11) 0.56246(6) 0.73467(5) 0.03589(19) Uani 1 1 d . . . . .
O2 O 1.13381(11) 0.19516(6) 0.46443(5) 0.03564(19) Uani 1 1 d . . . . .
O3 O -0.05355(10) 1.01173(6) 0.74471(5) 0.03370(18) Uani 1 1 d . . . . .
C1 C 0.66754(13) 0.55684(8) 0.51188(7) 0.0274(2) Uani 1 1 d . . . . .
H1 H 0.661274 0.620174 0.455344 0.033 Uiso 1 1 calc R U . . .
C2 C 0.78634(13) 0.46120(8) 0.50305(7) 0.0273(2) Uani 1 1 d . . . . .
C3 C 0.88359(14) 0.47275(8) 0.41361(8) 0.0294(2) Uani 1 1 d . . . . .
H3 H 0.868180 0.541432 0.362974 0.035 Uiso 1 1 calc R U . . .
C4 C 1.00207(14) 0.38660(9) 0.39678(8) 0.0306(2) Uani 1 1 d . . . . .
H4 H 1.067094 0.396237 0.335503 0.037 Uiso 1 1 calc R U . . .
C5 C 1.02427(13) 0.28600(9) 0.47083(8) 0.0288(2) Uani 1 1 d . . . . .
C6 C 0.92823(16) 0.27277(9) 0.56082(8) 0.0351(2) Uani 1 1 d . . . . .
H6 H 0.943899 0.203931 0.611248 0.042 Uiso 1 1 calc R U . . .
C7 C 0.81159(15) 0.35837(9) 0.57691(8) 0.0342(2) Uani 1 1 d . . . . .
H7 H 0.747210 0.348265 0.638403 0.041 Uiso 1 1 calc R U . . .
C8 C 0.38281(13) 0.65801(8) 0.66383(7) 0.0272(2) Uani 1 1 d . . . . .
C9 C 0.26369(13) 0.74789(8) 0.68629(8) 0.0280(2) Uani 1 1 d . . . . .
C10 C 0.22473(14) 0.84960(9) 0.61357(8) 0.0299(2) Uani 1 1 d . . . . .
H10 H 0.271917 0.859420 0.548677 0.036 Uiso 1 1 calc R U . . .
C11 C 0.11847(14) 0.93548(9) 0.63550(8) 0.0308(2) Uani 1 1 d . . . . .
H11 H 0.092871 1.004255 0.585847 0.037 Uiso 1 1 calc R U . . .
C12 C 0.04824(13) 0.92134(8) 0.73099(8) 0.0287(2) Uani 1 1 d . . . . .
C13 C 0.08462(15) 0.82052(9) 0.80366(8) 0.0323(2) Uani 1 1 d . . . . .
H13 H 0.036392 0.810575 0.868414 0.039 Uiso 1 1 calc R U . . .
C14 C 0.19204(15) 0.73443(9) 0.78083(8) 0.0324(2) Uani 1 1 d . . . . .
H14 H 0.216886 0.665512 0.830392 0.039 Uiso 1 1 calc R U . . .
C15 C 1.22819(14) 0.19779(9) 0.37266(8) 0.0304(2) Uani 1 1 d . . . . .
H15A H 1.308668 0.249546 0.351946 0.036 Uiso 1 1 calc R U . . .
H15B H 1.146547 0.220265 0.322483 0.036 Uiso 1 1 calc R U . . .
C16 C 1.32912(15) 0.08405(9) 0.38757(8) 0.0335(2) Uani 1 1 d . . . . .
H16A H 1.246622 0.033332 0.411179 0.040 Uiso 1 1 calc R U . . .
H16B H 1.409566 0.063293 0.438035 0.040 Uiso 1 1 calc R U . . .
C17 C 1.43381(14) 0.07284(9) 0.29542(8) 0.0306(2) Uani 1 1 d . . . . .
H17A H 1.519485 0.121465 0.273256 0.037 Uiso 1 1 calc R U . . .
H17B H 1.353966 0.096415 0.244184 0.037 Uiso 1 1 calc R U . . .
C18 C 1.53043(14) -0.04306(9) 0.30929(8) 0.0333(2) Uani 1 1 d . . . . .
H18A H 1.613807 -0.065745 0.358628 0.040 Uiso 1 1 calc R U . . .
H18B H 1.445452 -0.092223 0.333726 0.040 Uiso 1 1 calc R U . . .
C19 C 1.62908(14) -0.05396(9) 0.21568(8) 0.0314(2) Uani 1 1 d . . . . .
H19A H 1.714824 -0.005321 0.192145 0.038 Uiso 1 1 calc R U . . .
H19B H 1.545447 -0.029245 0.166179 0.038 Uiso 1 1 calc R U . . .
C20 C 1.72483(14) -0.16876(9) 0.22542(8) 0.0331(2) Uani 1 1 d . . . . .
H20A H 1.815492 -0.191488 0.270753 0.040 Uiso 1 1 calc R U . . .
H20B H 1.641130 -0.218616 0.253624 0.040 Uiso 1 1 calc R U . . .
C21 C 1.81039(14) -0.17897(9) 0.12934(9) 0.0350(2) Uani 1 1 d . . . . .
H21A H 1.893812 -0.128940 0.101082 0.042 Uiso 1 1 calc R U . . .
H21B H 1.719634 -0.156343 0.084075 0.042 Uiso 1 1 calc R U . . .
C22 C 1.90660(17) -0.29354(11) 0.13876(11) 0.0457(3) Uani 1 1 d . . . . .
H22A H 1.998909 -0.315841 0.182063 0.069 Uiso 1 1 calc R U . . .
H22B H 1.958321 -0.295040 0.074821 0.069 Uiso 1 1 calc R U . . .
H22C H 1.824421 -0.343403 0.165445 0.069 Uiso 1 1 calc R U . . .
C23 C -0.12457(14) 1.00534(9) 0.84114(8) 0.0307(2) Uani 1 1 d . . . . .
H23A H -0.029849 0.980779 0.884264 0.037 Uiso 1 1 calc R U . . .
H23B H -0.204792 0.953207 0.867080 0.037 Uiso 1 1 calc R U . . .
C24 C -0.22180(14) 1.11744(9) 0.83568(8) 0.0301(2) Uani 1 1 d . . . . .
H24A H -0.314746 1.141045 0.791578 0.036 Uiso 1 1 calc R U . . .
H24B H -0.140286 1.168731 0.808088 0.036 Uiso 1 1 calc R U . . .
C25 C -0.30339(14) 1.12168(9) 0.93454(8) 0.0316(2) Uani 1 1 d . . . . .
H25A H -0.386245 1.071218 0.961772 0.038 Uiso 1 1 calc R U . . .
H25B H -0.210740 1.097218 0.978940 0.038 Uiso 1 1 calc R U . . .
C26 C -0.39918(15) 1.23533(9) 0.92864(8) 0.0328(2) Uani 1 1 d . . . . .
H26A H -0.313637 1.284065 0.906211 0.039 Uiso 1 1 calc R U . . .
H26B H -0.483804 1.261915 0.879436 0.039 Uiso 1 1 calc R U . . .
C27 C -0.49580(16) 1.24277(10) 1.02328(8) 0.0375(3) Uani 1 1 d . . . . .
H27A H -0.410438 1.221449 1.071338 0.045 Uiso 1 1 calc R U . . .
H27B H -0.575989 1.190605 1.048176 0.045 Uiso 1 1 calc R U . . .
C28 C -0.60011(18) 1.35550(10) 1.01364(9) 0.0420(3) Uani 1 1 d . . . . .
H28A H -0.518480 1.406700 0.991239 0.050 Uiso 1 1 calc R U . . .
H28B H -0.680652 1.377896 0.962930 0.050 Uiso 1 1 calc R U . . .
C29 C -0.7041(2) 1.36570(13) 1.10406(12) 0.0638(4) Uani 1 1 d . . . . .
H29A H -0.622537 1.349029 1.153101 0.077 Uiso 1 1 calc R U . . .
H29B H -0.778755 1.310376 1.129375 0.077 Uiso 1 1 calc R U . . .
C30 C -0.8179(2) 1.47465(13) 1.09302(12) 0.0598(4) Uani 1 1 d . . . . .
H30A H -0.745045 1.529748 1.072234 0.090 Uiso 1 1 calc R U . . .
H30B H -0.883813 1.472741 1.155202 0.090 Uiso 1 1 calc R U . . .
H30C H -0.899186 1.492568 1.044425 0.090 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
B1 F2 1.3671(14) . ?
B1 F1 1.3712(13) . ?
B1 O1 1.4677(13) . ?
B1 N1 1.6072(14) . ?
N1 C1 1.2949(13) . ?
N1 N2 1.4090(11) . ?
N2 C8 1.2990(13) . ?
O1 C8 1.3266(13) . ?
O2 C5 1.3528(12) . ?
O2 C15 1.4385(12) . ?
O3 C12 1.3625(12) . ?
O3 C23 1.4345(12) . ?
C1 C2 1.4456(14) . ?
C2 C3 1.3979(14) . ?
C2 C7 1.4100(15) . ?
C3 C4 1.3880(14) . ?
C4 C5 1.3906(15) . ?
C5 C6 1.3982(15) . ?
C6 C7 1.3718(15) . ?
C8 C9 1.4631(14) . ?
C9 C14 1.3915(15) . ?
C9 C10 1.4013(15) . ?
C10 C11 1.3779(14) . ?
C11 C12 1.4002(14) . ?
C12 C13 1.3909(15) . ?
C13 C14 1.3896(15) . ?
C15 C16 1.5108(14) . ?
C16 C17 1.5224(14) . ?
C17 C18 1.5280(14) . ?
C18 C19 1.5233(14) . ?
C19 C20 1.5247(14) . ?
C20 C21 1.5224(15) . ?
C21 C22 1.5240(16) . ?
C23 C24 1.5104(14) . ?
C24 C25 1.5261(14) . ?
C25 C26 1.5241(14) . ?
C26 C27 1.5168(15) . ?
C27 C28 1.5211(16) . ?
C28 C29 1.4940(18) . ?
C29 C30 1.5018(19) . ?

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
F2 B1 F1 112.43(9) . . ?
F2 B1 O1 112.29(9) . . ?
F1 B1 O1 111.60(9) . . ?
F2 B1 N1 110.35(9) . . ?
F1 B1 N1 111.18(9) . . ?
O1 B1 N1 98.17(8) . . ?
C1 N1 N2 117.07(8) . . ?
C1 N1 B1 134.35(8) . . ?
N2 N1 B1 108.53(7) . . ?
C8 N2 N1 105.09(8) . . ?
C8 O1 B1 108.83(8) . . ?
C5 O2 C15 118.99(8) . . ?
C12 O3 C23 118.63(8) . . ?
N1 C1 C2 127.64(9) . . ?
C3 C2 C7 117.94(9) . . ?
C3 C2 C1 116.69(9) . . ?
C7 C2 C1 125.37(9) . . ?
C4 C3 C2 121.80(10) . . ?
C3 C4 C5 119.09(10) . . ?
O2 C5 C4 125.43(9) . . ?
O2 C5 C6 114.58(9) . . ?
C4 C5 C6 119.99(9) . . ?
C7 C6 C5 120.56(10) . . ?
C6 C7 C2 120.62(10) . . ?
N2 C8 O1 119.37(9) . . ?
N2 C8 C9 122.67(9) . . ?
O1 C8 C9 117.95(9) . . ?
C14 C9 C10 119.11(9) . . ?
C14 C9 C8 120.37(9) . . ?
C10 C9 C8 120.49(9) . . ?
C11 C10 C9 120.48(10) . . ?
C10 C11 C12 119.97(10) . . ?
O3 C12 C13 124.82(9) . . ?
O3 C12 C11 115.09(9) . . ?
C13 C12 C11 120.09(9) . . ?
C14 C13 C12 119.51(10) . . ?
C13 C14 C9 120.84(10) . . ?
O2 C15 C16 106.29(8) . . ?
C15 C16 C17 112.69(9) . . ?
C16 C17 C18 112.82(9) . . ?
C19 C18 C17 112.26(9) . . ?
C18 C19 C20 114.23(9) . . ?
C21 C20 C19 113.08(9) . . ?
C20 C21 C22 113.26(10) . . ?
O3 C23 C24 107.26(8) . . ?
C23 C24 C25 112.42(9) . . ?
C26 C25 C24 112.11(9) . . ?
C27 C26 C25 114.49(9) . . ?
C26 C27 C28 113.28(10) . . ?
C29 C28 C27 115.26(11) . . ?
C28 C29 C30 115.39(13) . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.034

