# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_a
_database_code_depnum_ccdc_archive 'CCDC 1976108'
loop_
_audit_author_name
_audit_author_address
'Liu  Yongjun'
;Ningbo University of Technology
China
;
_audit_update_record             
;
2020-01-08 deposited with the CCDC.	2020-05-26 downloaded from the CCDC.
;
_audit_creation_date             2019-12-19
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.17(B C18 N O4)'
_chemical_formula_sum            'C H B N O'
_chemical_formula_weight         53.84
_chemical_absolute_configuration ?
_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 0.0033 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'
O O 0.0106 0.0060 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   7.2859(7)
_cell_length_b                   8.4515(8)
_cell_length_c                   25.879(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1593.6(3)
_cell_formula_units_Z            24
_cell_measurement_reflns_used    1801
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      21.97
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             648
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_unetI/netI     0.1414
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8560
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.444
_diffrn_reflns_theta_min         2.535
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                1802
_reflns_number_total             3610
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.516
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details 
;
 Flack x determined using 544 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2238
_refine_ls_R_factor_gt           0.1217
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.066
_refine_ls_shift/su_mean         0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1700P)²+3.9262P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2984
_refine_ls_wR_factor_ref         0.3555
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_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
O001 O 0.5612(8) 0.5466(6) 0.4166(2) 0.0313(15) Uiso 1 1 d . . . . .
O002 O 0.7806(9) 0.4695(7) 0.4823(2) 0.0390(16) Uiso 1 1 d . . . . .
O003 O 0.3685(11) 0.4922(9) 0.3520(3) 0.058(2) Uiso 1 1 d . . . . .
N004 N 0.7990(11) 0.3651(8) 0.3961(3) 0.0324(18) Uiso 1 1 d . . . . .
C005 C 0.7008(13) 0.8459(10) 0.3524(3) 0.032(2) Uiso 1 1 d . . . . .
O006 O 0.7773(13) 0.2427(11) 0.5261(3) 0.075(3) Uiso 1 1 d . . . . .
C007 C 0.8643(13) 0.7538(10) 0.3650(3) 0.029(2) Uiso 1 1 d . . . . .
C008 C 0.5159(14) 0.4767(11) 0.3731(3) 0.037(2) Uiso 1 1 d . . . . .
C009 C 0.8859(12) 0.6754(10) 0.4169(3) 0.029(2) Uiso 1 1 d . . . . .
C00A C 0.5639(14) 0.8816(11) 0.3894(4) 0.039(2) Uiso 1 1 d . . . . .
C00B C 0.6829(14) 0.9071(12) 0.3012(4) 0.040(2) Uiso 1 1 d . . . . .
C00C C 0.9972(14) 0.7343(12) 0.3286(4) 0.041(2) Uiso 1 1 d . . . . .
C00D C 1.0739(14) 0.6715(11) 0.4411(4) 0.038(2) Uiso 1 1 d . . . . .
C00E C 0.9321(15) 0.7832(12) 0.4626(4) 0.042(2) Uiso 1 1 d . . . . .
C00F C 0.6696(14) 0.3775(12) 0.3517(4) 0.041(2) Uiso 1 1 d . . . . .
C00G C 0.7409(15) 0.2418(12) 0.4335(4) 0.048(3) Uiso 1 1 d . . . . .
C00H C 0.7702(15) 0.3155(13) 0.4851(4) 0.047(3) Uiso 1 1 d . . . . .
C00I C 0.9915(16) 0.3353(13) 0.3769(4) 0.050(3) Uiso 1 1 d . . . . .
C00J C 0.9757(18) 0.7970(14) 0.2762(4) 0.059(3) Uiso 1 1 d . . . . .
C00K C 0.4095(16) 0.9668(13) 0.3760(4) 0.049(3) Uiso 1 1 d . . . . .
B00L B 0.7596(15) 0.5275(11) 0.4292(4) 0.027(2) Uiso 1 1 d . . . . .
C00M C 0.3919(18) 1.0201(15) 0.3248(5) 0.062(3) Uiso 1 1 d . . . . .
C00N C 0.5226(18) 0.9943(14) 0.2885(5) 0.060(3) Uiso 1 1 d . . . . .
C00O C 0.8226(16) 0.8786(13) 0.2646(4) 0.054(3) Uiso 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
O001 C008 1.315(10) . ?
O001 B00L 1.490(13) . ?
O002 C00H 1.306(12) . ?
O002 B00L 1.468(11) . ?
O003 C008 1.212(12) . ?
N004 C00F 1.489(12) . ?
N004 C00G 1.484(13) . ?
N004 C00I 1.508(14) . ?
N004 B00L 1.643(12) . ?
C005 C007 1.460(13) . ?
C005 C00A 1.415(13) . ?
C005 C00B 1.429(13) . ?
O006 C00H 1.228(12) . ?
C007 C009 1.507(12) . ?
C007 C00C 1.360(13) . ?
C008 C00F 1.505(13) . ?
C009 C00D 1.506(13) . ?
C009 C00E 1.530(13) . ?
C009 B00L 1.584(13) . ?
C00A C00K 1.380(15) . ?
C00B C00N 1.419(16) . ?
C00B C00O 1.411(15) . ?
C00C C00J 1.464(15) . ?
C00D C00E 1.506(14) . ?
C00G C00H 1.489(15) . ?
C00J C00O 1.346(16) . ?
C00K C00M 1.407(16) . ?
C00M C00N 1.355(17) . ?

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
C008 O001 B00L 112.4(7) . . ?
C00H O002 B00L 112.2(8) . . ?
C00F N004 C00I 110.3(7) . . ?
C00F N004 B00L 103.4(7) . . ?
C00G N004 C00F 111.8(8) . . ?
C00G N004 C00I 111.2(8) . . ?
C00G N004 B00L 101.3(6) . . ?
C00I N004 B00L 118.2(7) . . ?
C00A C005 C007 122.5(8) . . ?
C00A C005 C00B 119.1(8) . . ?
C00B C005 C007 118.3(8) . . ?
C005 C007 C009 121.3(8) . . ?
C00C C007 C005 119.4(8) . . ?
C00C C007 C009 119.3(8) . . ?
O001 C008 C00F 112.2(8) . . ?
O003 C008 O001 124.1(9) . . ?
O003 C008 C00F 123.7(9) . . ?
C007 C009 C00E 116.8(7) . . ?
C007 C009 B00L 117.7(7) . . ?
C00D C009 C007 118.3(8) . . ?
C00D C009 C00E 59.5(6) . . ?
C00D C009 B00L 115.4(7) . . ?
C00E C009 B00L 116.3(7) . . ?
C00K C00A C005 121.0(9) . . ?
C00N C00B C005 118.5(9) . . ?
C00O C00B C005 119.7(9) . . ?
C00O C00B C00N 121.8(9) . . ?
C007 C00C C00J 121.4(10) . . ?
C009 C00D C00E 61.1(7) . . ?
C00D C00E C009 59.5(6) . . ?
N004 C00F C008 103.1(7) . . ?
N004 C00G C00H 104.5(8) . . ?
O002 C00H C00G 112.1(9) . . ?
O006 C00H O002 123.0(10) . . ?
O006 C00H C00G 124.9(10) . . ?
C00O C00J C00C 118.8(11) . . ?
C00A C00K C00M 118.6(10) . . ?
O001 B00L N004 98.4(6) . . ?
O001 B00L C009 115.7(7) . . ?
O002 B00L O001 110.0(7) . . ?
O002 B00L N004 101.0(6) . . ?
O002 B00L C009 112.9(7) . . ?
C009 B00L N004 117.0(7) . . ?
C00N C00M C00K 122.6(12) . . ?
C00M C00N C00B 120.1(11) . . ?
C00J C00O C00B 122.4(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
