# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_n200110a
_database_code_depnum_ccdc_archive 'CCDC 2075408'
loop_
_audit_author_name
_audit_author_address
'Dawei Tian'
;Tianjin Normal University
China
;
_audit_update_record             
;
2021-04-05 deposited with the CCDC.	2021-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 B N S'
_chemical_formula_weight         235.10

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'
S S 0.1246 0.1234 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.977(7)
_cell_length_b                   8.264(10)
_cell_length_c                   24.38(3)
_cell_angle_alpha                89.28(2)
_cell_angle_beta                 101.30(3)
_cell_angle_gamma                90.04(2)
_cell_volume                     1181(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2697
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.91

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   0.948
_exptl_transmission_factor_max   0.957
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.246
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4977
_diffrn_reflns_av_unetI/netI     0.1185
_diffrn_reflns_av_R_equivalents  0.1151
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.704
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             2391
_reflns_number_gt                1813
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1846P)²+5.1417P] 
 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         2391
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1569
_refine_ls_R_factor_gt           0.1273
_refine_ls_wR_factor_ref         0.3864
_refine_ls_wR_factor_gt          0.3732
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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
S1 S -0.1127(3) 0.1673(3) 0.20698(8) 0.0465(6) Uani 1 1 d . . . . .
N1 N 0.4932(9) 0.3575(7) 0.2847(2) 0.0389(13) Uani 1 1 d . . . . .
H1 H 0.6108 0.3995 0.2747 0.047 Uiso 1 1 calc R U . . .
B1 B 0.3070(12) 0.3064(9) 0.2428(3) 0.0363(15) Uani 1 1 d . . . . .
C1 C 0.1067(10) 0.2208(8) 0.2629(3) 0.0375(14) Uani 1 1 d . . . . .
C2 C 0.1080(11) 0.1994(8) 0.3191(3) 0.0404(15) Uani 1 1 d . . . . .
H2 H -0.0109 0.1456 0.3311 0.049 Uiso 1 1 calc R U . . .
C3 C 0.3001(11) 0.2629(9) 0.3595(3) 0.0399(15) Uani 1 1 d . . . . .
C4 C 0.3026(13) 0.2532(11) 0.4178(3) 0.0513(18) Uani 1 1 d . . . . .
H4 H 0.1811 0.2042 0.4302 0.062 Uiso 1 1 calc R U . . .
C5 C 0.4809(16) 0.3148(12) 0.4565(3) 0.061(2) Uani 1 1 d . . . . .
H5 H 0.4798 0.3065 0.4946 0.073 Uiso 1 1 calc R U . . .
C6 C 0.6643(15) 0.3900(11) 0.4381(3) 0.059(2) Uani 1 1 d . . . . .
H6 H 0.7826 0.4332 0.4643 0.070 Uiso 1 1 calc R U . . .
C7 C 0.6732(12) 0.4015(10) 0.3821(3) 0.0500(18) Uani 1 1 d . . . . .
H7 H 0.7987 0.4487 0.3709 0.060 Uiso 1 1 calc R U . . .
C8 C 0.4906(11) 0.3413(8) 0.3417(3) 0.0393(15) Uani 1 1 d . . . . .
C9 C 0.2518(11) 0.3261(8) 0.1778(3) 0.0388(14) Uani 1 1 d . . . . .
C10 C 0.3672(13) 0.3997(9) 0.1389(3) 0.0470(16) Uani 1 1 d . . . . .
H10 H 0.5110 0.4441 0.1512 0.056 Uiso 1 1 calc R U . . .
C11 C 0.2678(15) 0.4066(11) 0.0820(3) 0.057(2) Uani 1 1 d . . . . .
H11 H 0.3435 0.4580 0.0568 0.069 Uiso 1 1 calc R U . . .
C12 C 0.0555(16) 0.3364(12) 0.0631(3) 0.061(2) Uani 1 1 d . . . . .
H12 H -0.0060 0.3387 0.0250 0.074 Uiso 1 1 calc R U . . .
C13 C -0.0686(13) 0.2625(10) 0.0996(3) 0.0492(17) Uani 1 1 d . . . . .
H13 H -0.2112 0.2174 0.0863 0.059 Uiso 1 1 calc R U . . .
C14 C 0.0293(11) 0.2587(8) 0.1568(3) 0.0404(15) 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
S1 C1 1.757(7) . ?
S1 C14 1.781(7) . ?
N1 C8 1.397(9) . ?
N1 B1 1.423(9) . ?
N1 H1 0.8600 . ?
B1 C1 1.548(9) . ?
B1 C9 1.560(10) . ?
C1 C2 1.379(10) . ?
C2 C3 1.460(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.420(10) . ?
C3 C8 1.446(10) . ?
C4 C5 1.380(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(13) . ?
C5 H5 0.9300 . ?
C6 C7 1.379(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.414(10) . ?
C7 H7 0.9300 . ?
C9 C10 1.409(10) . ?
C9 C14 1.443(9) . ?
C10 C11 1.398(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.399(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.402(10) . ?
C13 H13 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
C1 S1 C14 92.3(3) . . ?
C8 N1 B1 122.0(6) . . ?
C8 N1 H1 119.0 . . ?
B1 N1 H1 119.0 . . ?
N1 B1 C1 117.0(6) . . ?
N1 B1 C9 133.0(6) . . ?
C1 B1 C9 109.9(6) . . ?
C2 C1 B1 120.9(6) . . ?
C2 C1 S1 126.8(5) . . ?
B1 C1 S1 112.2(5) . . ?
C1 C2 C3 118.5(6) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C8 117.7(6) . . ?
C4 C3 C2 120.7(6) . . ?
C8 C3 C2 121.5(6) . . ?
C5 C4 C3 121.6(7) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 119.5(7) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 121.7(8) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 119.7(7) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
N1 C8 C7 120.4(6) . . ?
N1 C8 C3 119.9(6) . . ?
C7 C8 C3 119.8(6) . . ?
C10 C9 C14 117.7(6) . . ?
C10 C9 B1 133.5(6) . . ?
C14 C9 B1 108.8(6) . . ?
C11 C10 C9 120.7(7) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 119.9(7) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 122.2(7) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C12 C13 C14 117.8(7) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
C13 C14 C9 121.7(6) . . ?
C13 C14 S1 121.7(6) . . ?
C9 C14 S1 116.6(5) . . ?

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
C8 N1 B1 C1 -4.1(9) . . . . ?
C8 N1 B1 C9 172.2(7) . . . . ?
N1 B1 C1 C2 1.6(9) . . . . ?
C9 B1 C1 C2 -175.5(6) . . . . ?
N1 B1 C1 S1 179.1(5) . . . . ?
C9 B1 C1 S1 2.0(7) . . . . ?
C14 S1 C1 C2 174.4(6) . . . . ?
C14 S1 C1 B1 -2.8(5) . . . . ?
B1 C1 C2 C3 1.5(9) . . . . ?
S1 C1 C2 C3 -175.5(5) . . . . ?
C1 C2 C3 C4 176.0(7) . . . . ?
C1 C2 C3 C8 -2.4(10) . . . . ?
C8 C3 C4 C5 -0.6(11) . . . . ?
C2 C3 C4 C5 -179.0(7) . . . . ?
C3 C4 C5 C6 0.4(13) . . . . ?
C4 C5 C6 C7 -1.2(13) . . . . ?
C5 C6 C7 C8 2.1(13) . . . . ?
B1 N1 C8 C7 -176.5(7) . . . . ?
B1 N1 C8 C3 3.4(9) . . . . ?
C6 C7 C8 N1 177.6(7) . . . . ?
C6 C7 C8 C3 -2.2(11) . . . . ?
C4 C3 C8 N1 -178.4(6) . . . . ?
C2 C3 C8 N1 0.0(9) . . . . ?
C4 C3 C8 C7 1.4(10) . . . . ?
C2 C3 C8 C7 179.9(7) . . . . ?
N1 B1 C9 C10 0.5(13) . . . . ?
C1 B1 C9 C10 176.9(7) . . . . ?
N1 B1 C9 C14 -176.2(7) . . . . ?
C1 B1 C9 C14 0.3(7) . . . . ?
C14 C9 C10 C11 0.1(11) . . . . ?
B1 C9 C10 C11 -176.3(7) . . . . ?
C9 C10 C11 C12 -1.8(12) . . . . ?
C10 C11 C12 C13 2.2(13) . . . . ?
C11 C12 C13 C14 -0.8(13) . . . . ?
C12 C13 C14 C9 -0.9(11) . . . . ?
C12 C13 C14 S1 -179.8(6) . . . . ?
C10 C9 C14 C13 1.3(10) . . . . ?
B1 C9 C14 C13 178.5(7) . . . . ?
C10 C9 C14 S1 -179.8(5) . . . . ?
B1 C9 C14 S1 -2.5(7) . . . . ?
C1 S1 C14 C13 -177.8(6) . . . . ?
C1 S1 C14 C9 3.3(5) . . . . ?

_refine_diff_density_max         0.605
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.105

_shelxl_version_number           2013-2



