# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_20211224-myq
_database_code_depnum_ccdc_archive 'CCDC 2151731'
loop_
_audit_author_name
_audit_author_address
abc
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2022-02-13 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2021-12-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H33 B N2 S'
_chemical_formula_sum            'C20 H33 B N2 S'
_chemical_formula_weight         344.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 N1 S1 B1'
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'
S S 0.3331 0.5567 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.8039(2)
_cell_length_b                   17.1774(4)
_cell_length_c                   14.8916(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.570(2)
_cell_angle_gamma                90
_cell_volume                     1995.48(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6364
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.6940
_cell_measurement_theta_min      5.1530
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    1.439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9265
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.440
_diffrn_reflns_theta_min         3.930
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00 -54.00   1.00    1.00    --  -35.62 128.00 164.00   36
  2  ω    -55.00 -12.00   1.00    1.00    --  -35.62 143.00 -25.00   43
  3  ω     42.00  90.00   1.00    1.00    --   35.62-128.00  89.00   48
  4  ω    106.00 164.00   1.00    1.00    --  107.12 128.00 164.00   58
  5  ω    105.00 130.00   1.00    1.00    --  107.12 143.00 -25.00   25
  6  ω     55.00  80.00   1.00    1.00    --  107.12-128.00  89.00   25
  7  ω     46.00 130.00   1.00    1.00    --  107.12-143.00 -80.00   84
  8  ω   -101.00 -20.00   1.00    1.00    --  -35.62 -57.00 -90.00   81
  9  ω    -30.00  34.00   1.00    1.00    --   35.62 -57.00-180.00   64
 10  ω     19.00 104.00   1.00    1.00    --   35.62  38.00  30.00   85
 11  ω     38.00 129.00   1.00    1.00    --  107.12 -30.00-180.00   91
 12  ω    107.00 134.00   1.00    1.00    --  107.12 111.00 150.00   27
 13  ω    101.00 153.00   1.00    1.00    --  107.12 111.00-150.00   52
 14  ω     63.00 110.00   1.00    1.00    --  107.12 -95.00  60.00   47
 15  ω     90.00 174.00   1.00    1.00    --  107.12  30.00   0.00   84
 16  ω     41.00 130.00   1.00    1.00    --  107.12 -77.00-120.00   89
 17  ω     39.00 117.00   1.00    1.00    --  107.12 -30.00  30.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0450092000
_diffrn_orient_matrix_UB_12      0.0537548000
_diffrn_orient_matrix_UB_13      -0.0787818000
_diffrn_orient_matrix_UB_21      0.0211535000
_diffrn_orient_matrix_UB_22      -0.0715695000
_diffrn_orient_matrix_UB_23      -0.0610027000
_diffrn_orient_matrix_UB_31      -0.1910846000
_diffrn_orient_matrix_UB_32      0.0047488000
_diffrn_orient_matrix_UB_33      -0.0282573000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                3580
_reflns_number_total             3794
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3794
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.135
_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)+(0.0545P)²+2.4705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1347
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H,H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22), C19(H19), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 B8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C12(H12), C11(H11)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C15(H15A,H15B,
 H15C), C20(H20A,H20B,H20C), C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C17(H17A,
 H17B,H17C)
;
_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
S7 S 0.39873(6) 0.29934(3) 0.38329(3) 0.01271(15) Uani 1 1 d . . . . .
N13 N 0.8203(2) 0.39223(10) 0.45457(11) 0.0140(4) Uani 1 1 d . . . . .
N10 N 0.7862(2) 0.28578(10) 0.52725(12) 0.0148(4) Uani 1 1 d . . . . .
C9 C 0.6987(3) 0.34606(12) 0.48972(13) 0.0118(4) Uani 1 1 d . . . . .
C4 C 0.6819(2) 0.40367(12) 0.14335(13) 0.0103(4) Uani 1 1 d . . . . .
C6 C 0.4564(2) 0.41234(12) 0.25356(13) 0.0100(4) Uani 1 1 d . . . . .
C5 C 0.5444(3) 0.44255(12) 0.18029(13) 0.0111(4) Uani 1 1 d . . . . .
H5 H 0.509575 0.489958 0.155758 0.013 Uiso 1 1 calc R U . . .
C22 C 0.7825(3) 0.43473(12) 0.06481(13) 0.0117(4) Uani 1 1 d . . . . .
H22 H 0.904233 0.427514 0.080567 0.014 Uiso 1 1 calc R U . . .
C1 C 0.5081(2) 0.34049(11) 0.29036(13) 0.0104(4) Uani 1 1 d . . . . .
C3 C 0.7298(3) 0.33237(12) 0.18108(13) 0.0112(4) Uani 1 1 d . . . . .
H3 H 0.820741 0.305455 0.156558 0.013 Uiso 1 1 calc R U . . .
C19 C 0.3050(3) 0.45732(12) 0.28982(13) 0.0122(4) Uani 1 1 d . . . . .
H19 H 0.284639 0.437861 0.350470 0.015 Uiso 1 1 calc R U . . .
C2 C 0.6478(3) 0.29970(11) 0.25368(13) 0.0112(4) Uani 1 1 d . . . . .
C24 C 0.7460(3) 0.38723(13) -0.02053(14) 0.0180(5) Uani 1 1 d . . . . .
H24A H 0.774141 0.333601 -0.009524 0.027 Uiso 1 1 calc R U . . .
H24B H 0.814253 0.406791 -0.068220 0.027 Uiso 1 1 calc R U . . .
H24C H 0.626766 0.391496 -0.037375 0.027 Uiso 1 1 calc R U . . .
C16 C 0.7057(3) 0.22098(12) 0.29029(14) 0.0145(4) Uani 1 1 d . . . . .
H16 H 0.677163 0.219275 0.353941 0.017 Uiso 1 1 calc R U . . .
C12 C 0.9804(3) 0.36043(14) 0.46920(15) 0.0202(5) Uani 1 1 d . . . . .
H12 H 1.083920 0.381094 0.450935 0.024 Uiso 1 1 calc R U . . .
C21 C 0.3356(3) 0.54495(12) 0.29703(15) 0.0182(5) Uani 1 1 d . . . . .
H21A H 0.442736 0.554403 0.328313 0.027 Uiso 1 1 calc R U . . .
H21B H 0.244321 0.568465 0.329419 0.027 Uiso 1 1 calc R U . . .
H21C H 0.338854 0.567049 0.237894 0.027 Uiso 1 1 calc R U . . .
C23 C 0.7570(3) 0.52129(12) 0.04577(14) 0.0174(4) Uani 1 1 d . . . . .
H23A H 0.641524 0.530161 0.024272 0.026 Uiso 1 1 calc R U . . .
H23B H 0.835537 0.537752 0.001054 0.026 Uiso 1 1 calc R U . . .
H23C H 0.777785 0.550417 0.099992 0.026 Uiso 1 1 calc R U . . .
C15 C 0.7893(3) 0.46469(13) 0.40557(15) 0.0197(5) Uani 1 1 d . . . . .
H15A H 0.770131 0.453452 0.342949 0.030 Uiso 1 1 calc R U . . .
H15B H 0.887110 0.498189 0.412923 0.030 Uiso 1 1 calc R U . . .
H15C H 0.690093 0.490092 0.428622 0.030 Uiso 1 1 calc R U . . .
C20 C 0.1443(3) 0.44036(14) 0.23236(16) 0.0199(5) Uani 1 1 d . . . . .
H20A H 0.163821 0.454742 0.171192 0.030 Uiso 1 1 calc R U . . .
H20B H 0.049843 0.469847 0.254489 0.030 Uiso 1 1 calc R U . . .
H20C H 0.118135 0.385821 0.235261 0.030 Uiso 1 1 calc R U . . .
C14 C 0.7088(3) 0.22088(14) 0.57480(17) 0.0240(5) Uani 1 1 d . . . . .
H14A H 0.665062 0.239070 0.630667 0.036 Uiso 1 1 calc R U . . .
H14B H 0.793668 0.181442 0.586417 0.036 Uiso 1 1 calc R U . . .
H14C H 0.616664 0.199473 0.538576 0.036 Uiso 1 1 calc R U . . .
C11 C 0.9587(3) 0.29370(14) 0.51498(15) 0.0202(5) Uani 1 1 d . . . . .
H11 H 1.044407 0.259557 0.534523 0.024 Uiso 1 1 calc R U . . .
C18 C 0.8974(3) 0.20711(14) 0.28455(17) 0.0252(5) Uani 1 1 d . . . . .
H18A H 0.926567 0.200007 0.222883 0.038 Uiso 1 1 calc R U . . .
H18B H 0.928409 0.161367 0.318275 0.038 Uiso 1 1 calc R U . . .
H18C H 0.958334 0.251210 0.308878 0.038 Uiso 1 1 calc R U . . .
B8 B 0.4944(3) 0.35767(14) 0.48497(15) 0.0146(5) Uani 1 1 d . . . . .
H8A H 0.467240 0.412490 0.478091 0.017 Uiso 1 1 calc R U . . .
H8B H 0.445042 0.339360 0.540179 0.017 Uiso 1 1 calc R U . . .
C17 C 0.6041(4) 0.15646(14) 0.24253(19) 0.0377(7) Uani 1 1 d . . . . .
H17A H 0.483629 0.166003 0.248047 0.057 Uiso 1 1 calc R U . . .
H17B H 0.632860 0.107187 0.269376 0.057 Uiso 1 1 calc R U . . .
H17C H 0.631908 0.155619 0.180138 0.057 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
S7 C1 1.791(2) . ?
S7 B8 1.947(2) . ?
N13 C9 1.353(3) . ?
N13 C12 1.375(3) . ?
N13 C15 1.460(3) . ?
N10 C9 1.353(3) . ?
N10 C14 1.461(3) . ?
N10 C11 1.370(3) . ?
C9 B8 1.606(3) . ?
C4 C5 1.391(3) . ?
C4 C22 1.523(3) . ?
C4 C3 1.394(3) . ?
C6 C5 1.404(3) . ?
C6 C1 1.405(3) . ?
C6 C19 1.524(3) . ?
C5 H5 0.9300 . ?
C22 H22 0.9800 . ?
C22 C24 1.530(3) . ?
C22 C23 1.526(3) . ?
C1 C2 1.418(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.390(3) . ?
C19 H19 0.9800 . ?
C19 C21 1.527(3) . ?
C19 C20 1.527(3) . ?
C2 C16 1.522(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C16 H16 0.9800 . ?
C16 C18 1.520(3) . ?
C16 C17 1.527(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.347(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C11 H11 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
B8 H8A 0.9700 . ?
B8 H8B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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 S7 B8 102.53(9) . . ?
C9 N13 C12 110.46(18) . . ?
C9 N13 C15 125.76(18) . . ?
C12 N13 C15 123.76(18) . . ?
C9 N10 C14 125.00(19) . . ?
C9 N10 C11 110.85(18) . . ?
C11 N10 C14 124.16(19) . . ?
N13 C9 B8 128.02(18) . . ?
N10 C9 N13 104.87(18) . . ?
N10 C9 B8 127.06(18) . . ?
C5 C4 C22 123.74(18) . . ?
C5 C4 C3 117.63(18) . . ?
C3 C4 C22 118.63(17) . . ?
C5 C6 C1 119.13(18) . . ?
C5 C6 C19 119.23(17) . . ?
C1 C6 C19 121.62(17) . . ?
C4 C5 C6 121.93(18) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C4 C22 H22 106.8 . . ?
C4 C22 C24 111.28(16) . . ?
C4 C22 C23 114.62(17) . . ?
C24 C22 H22 106.8 . . ?
C23 C22 H22 106.8 . . ?
C23 C22 C24 110.17(17) . . ?
C6 C1 S7 120.70(15) . . ?
C6 C1 C2 119.94(18) . . ?
C2 C1 S7 119.35(15) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 C4 122.97(18) . . ?
C2 C3 H3 118.5 . . ?
C6 C19 H19 107.5 . . ?
C6 C19 C21 113.79(17) . . ?
C6 C19 C20 109.75(17) . . ?
C21 C19 H19 107.5 . . ?
C20 C19 H19 107.5 . . ?
C20 C19 C21 110.61(18) . . ?
C1 C2 C16 121.67(18) . . ?
C3 C2 C1 118.39(18) . . ?
C3 C2 C16 119.92(18) . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C2 C16 H16 107.5 . . ?
C2 C16 C17 109.43(17) . . ?
C18 C16 C2 113.72(18) . . ?
C18 C16 H16 107.5 . . ?
C18 C16 C17 111.1(2) . . ?
C17 C16 H16 107.5 . . ?
N13 C12 H12 126.5 . . ?
C11 C12 N13 107.0(2) . . ?
C11 C12 H12 126.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N13 C15 H15A 109.5 . . ?
N13 C15 H15B 109.5 . . ?
N13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N10 C14 H14A 109.5 . . ?
N10 C14 H14B 109.5 . . ?
N10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N10 C11 H11 126.6 . . ?
C12 C11 N10 106.81(19) . . ?
C12 C11 H11 126.6 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
S7 B8 H8A 109.8 . . ?
S7 B8 H8B 109.8 . . ?
C9 B8 S7 109.23(14) . . ?
C9 B8 H8A 109.8 . . ?
C9 B8 H8B 109.8 . . ?
H8A B8 H8B 108.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
S7 C1 C2 C3 179.44(14) . . . . ?
S7 C1 C2 C16 1.0(3) . . . . ?
N13 C9 B8 S7 94.3(2) . . . . ?
N13 C12 C11 N10 0.2(2) . . . . ?
N10 C9 B8 S7 -82.9(2) . . . . ?
C9 N13 C12 C11 -0.6(2) . . . . ?
C9 N10 C11 C12 0.3(2) . . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C4 C3 C2 C16 179.07(18) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C6 C1 C2 C16 -178.79(17) . . . . ?
C5 C4 C22 C24 -109.2(2) . . . . ?
C5 C4 C22 C23 16.6(3) . . . . ?
C5 C4 C3 C2 -0.7(3) . . . . ?
C5 C6 C1 S7 -179.54(15) . . . . ?
C5 C6 C1 C2 0.3(3) . . . . ?
C5 C6 C19 C21 -42.8(3) . . . . ?
C5 C6 C19 C20 81.7(2) . . . . ?
C22 C4 C5 C6 -179.12(18) . . . . ?
C22 C4 C3 C2 179.02(18) . . . . ?
C1 C6 C5 C4 -0.4(3) . . . . ?
C1 C6 C19 C21 138.58(19) . . . . ?
C1 C6 C19 C20 -96.9(2) . . . . ?
C1 C2 C16 C18 -147.4(2) . . . . ?
C1 C2 C16 C17 87.7(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C22 C24 71.0(2) . . . . ?
C3 C4 C22 C23 -163.12(18) . . . . ?
C3 C2 C16 C18 34.2(3) . . . . ?
C3 C2 C16 C17 -90.6(3) . . . . ?
C19 C6 C5 C4 -179.03(18) . . . . ?
C19 C6 C1 S7 -1.0(3) . . . . ?
C19 C6 C1 C2 178.86(18) . . . . ?
C12 N13 C9 N10 0.7(2) . . . . ?
C12 N13 C9 B8 -177.00(19) . . . . ?
C15 N13 C9 N10 179.15(18) . . . . ?
C15 N13 C9 B8 1.4(3) . . . . ?
C15 N13 C12 C11 -179.04(19) . . . . ?
C14 N10 C9 N13 179.19(19) . . . . ?
C14 N10 C9 B8 -3.0(3) . . . . ?
C14 N10 C11 C12 -179.5(2) . . . . ?
C11 N10 C9 N13 -0.6(2) . . . . ?
C11 N10 C9 B8 177.15(19) . . . . ?
B8 S7 C1 C6 -79.02(17) . . . . ?
B8 S7 C1 C2 101.16(17) . . . . ?

_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 1.440
_oxdiff_exptl_absorpt_empirical_full_min 0.588
####################################################################### 
# 
# 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_myq
_database_code_depnum_ccdc_archive 'CCDC 2151733'
loop_
_audit_author_name
_audit_author_address
abc
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2022-02-13 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2021-09-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 B N3 O'
_chemical_formula_sum            'C15 H20 B N3 O'
_chemical_formula_weight         269.15
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 O1 N1 B1 '
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'

_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                   6.2427(5)
_cell_length_b                   7.8871(6)
_cell_length_c                   29.178(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1436.64(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1659
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2160
_cell_measurement_theta_min      5.8180
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.994
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            3502
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.537
_diffrn_reflns_theta_min         5.811
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00  -4.00   1.00    2.99    --  -35.75 -17.00-127.00   82
  2  ω    -73.00 -41.00   1.00    2.99    --  -35.75 109.00-179.00   32
  3  ω    100.00 143.00   1.00   11.97    --  107.12 109.00-179.00   43
  4  ω     40.00  66.00   1.00   11.97    --  107.12 -17.00-127.00   26
  5  ω     42.00  91.00   1.00   11.97    --  107.12-132.00-171.00   49
  6  ω     64.00 108.00   1.00    2.99    --   35.75 178.00-150.00   44
  7  ω     43.00  99.00   1.00    2.99    --   35.75  57.00-120.00   56
  8  ω     77.00 111.00   1.00   11.97    --  107.12-111.00  60.00   34
  9  ω     39.00 117.00   1.00   11.97    --  107.12 -30.00 -90.00   78
 10  ω     42.00 121.00   1.00   11.97    --  107.12 -61.00-180.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0376419000
_diffrn_orient_matrix_UB_12      -0.1300647000
_diffrn_orient_matrix_UB_13      0.0385791000
_diffrn_orient_matrix_UB_21      -0.0340447000
_diffrn_orient_matrix_UB_22      0.1401129000
_diffrn_orient_matrix_UB_23      0.0360974000
_diffrn_orient_matrix_UB_31      -0.2413904000
_diffrn_orient_matrix_UB_32      -0.0399652000
_diffrn_orient_matrix_UB_33      0.0008880000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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         0.688
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                1869
_reflns_number_total             2428
_reflns_odcompleteness_completeness 99.42
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.096
_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)+(0.0255P)²+0.9137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1264
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C5(H5), C8(H8), C14(H14), C7(H7), C6(H6)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_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
O19 O -0.2213(5) -0.6492(4) -0.42281(11) 0.0508(9) Uani 1 1 d . . . . .
N16 N -0.7124(6) -0.0367(5) -0.39628(11) 0.0383(8) Uani 1 1 d . . . . .
N10 N -0.4049(6) -0.6738(5) -0.35607(13) 0.0407(9) Uani 1 1 d . . . . .
N13 N -0.5312(6) -0.0583(5) -0.45778(11) 0.0417(9) Uani 1 1 d . . . . .
C1 C -0.3672(6) -0.5973(6) -0.39780(14) 0.0368(10) Uani 1 1 d . . . . .
C2 C -0.5062(6) -0.4511(6) -0.41026(13) 0.0354(9) Uani 1 1 d . . . . .
H2 H -0.512291 -0.447044 -0.443804 0.042 Uiso 1 1 calc R U . . .
C12 C -0.5433(7) -0.1184(6) -0.41454(14) 0.0374(10) Uani 1 1 d . . . . .
C4 C -0.7377(6) -0.5239(5) -0.34297(13) 0.0359(9) Uani 1 1 d . . . . .
C3 C -0.7368(6) -0.4792(5) -0.39315(13) 0.0362(9) Uani 1 1 d . . . . .
H3A H -0.820067 -0.376862 -0.397988 0.043 Uiso 1 1 calc R U . . .
H3B H -0.802927 -0.569996 -0.410543 0.043 Uiso 1 1 calc R U . . .
C9 C -0.5695(7) -0.6207(6) -0.32575(14) 0.0372(10) Uani 1 1 d . . . . .
C15 C -0.8047(8) 0.0708(6) -0.42791(17) 0.0475(11) Uani 1 1 d . . . . .
H15 H -0.924685 0.138543 -0.423267 0.057 Uiso 1 1 calc R U . . .
C5 C -0.9043(8) -0.4797(6) -0.31390(16) 0.0475(11) Uani 1 1 d . . . . .
H5 H -1.017734 -0.415603 -0.325174 0.057 Uiso 1 1 calc R U . . .
C8 C -0.5691(9) -0.6697(6) -0.27981(15) 0.0503(13) Uani 1 1 d . . . . .
H8 H -0.455461 -0.732324 -0.268064 0.060 Uiso 1 1 calc R U . . .
C14 C -0.6904(8) 0.0598(6) -0.46628(16) 0.0472(12) Uani 1 1 d . . . . .
H14 H -0.713003 0.119396 -0.493354 0.057 Uiso 1 1 calc R U . . .
C18 C -0.7916(8) -0.0575(7) -0.34936(15) 0.0506(12) Uani 1 1 d . . . . .
H18A H -0.701855 -0.136297 -0.333242 0.076 Uiso 1 1 calc R U . . .
H18B H -0.935744 -0.099835 -0.350137 0.076 Uiso 1 1 calc R U . . .
H18C H -0.789164 0.050048 -0.333959 0.076 Uiso 1 1 calc R U . . .
C20 C -0.2660(8) -0.8150(6) -0.34328(17) 0.0544(13) Uani 1 1 d . . . . .
H20A H -0.151009 -0.774078 -0.324438 0.082 Uiso 1 1 calc R U . . .
H20B H -0.208114 -0.866248 -0.370445 0.082 Uiso 1 1 calc R U . . .
H20C H -0.347422 -0.897678 -0.326557 0.082 Uiso 1 1 calc R U . . .
C7 C -0.7388(10) -0.6246(7) -0.25178(16) 0.0589(15) Uani 1 1 d . . . . .
H7 H -0.739945 -0.659475 -0.221336 0.071 Uiso 1 1 calc R U . . .
C6 C -0.9048(9) -0.5293(8) -0.26836(16) 0.0608(15) Uani 1 1 d . . . . .
H6 H -1.017087 -0.498043 -0.249187 0.073 Uiso 1 1 calc R U . . .
C17 C -0.3670(9) -0.1034(8) -0.49094(17) 0.0714(18) Uani 1 1 d . . . . .
H17A H -0.341635 -0.223374 -0.489728 0.107 Uiso 1 1 calc R U . . .
H17B H -0.236956 -0.044012 -0.483857 0.107 Uiso 1 1 calc R U . . .
H17C H -0.414100 -0.072673 -0.521143 0.107 Uiso 1 1 calc R U . . .
B11 B -0.3997(8) -0.2679(7) -0.39277(18) 0.0383(11) Uani 1 1 d . . . . .
H11A H -0.403(6) -0.254(5) -0.3526(13) 0.027(10) Uiso 1 1 d . . . . .
H11B H -0.233(8) -0.266(6) -0.4055(15) 0.059(15) 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
O19 C1 1.237(5) . ?
N16 C12 1.347(5) . ?
N16 C15 1.379(6) . ?
N16 C18 1.465(5) . ?
N10 C1 1.379(5) . ?
N10 C9 1.419(5) . ?
N10 C20 1.460(5) . ?
N13 C12 1.350(5) . ?
N13 C14 1.385(6) . ?
N13 C17 1.454(6) . ?
C1 C2 1.488(6) . ?
C2 H2 0.9800 . ?
C2 C3 1.540(5) . ?
C2 B11 1.671(7) . ?
C12 B11 1.612(7) . ?
C4 C3 1.506(5) . ?
C4 C9 1.392(6) . ?
C4 C5 1.387(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C9 C8 1.395(6) . ?
C15 H15 0.9300 . ?
C15 C14 1.330(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(7) . ?
C8 H8 0.9300 . ?
C8 C7 1.385(7) . ?
C14 H14 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C7 H7 0.9300 . ?
C7 C6 1.369(8) . ?
C6 H6 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
B11 H11A 1.18(4) . ?
B11 H11B 1.11(5) . ?

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
C12 N16 C15 110.9(4) . . ?
C12 N16 C18 125.5(4) . . ?
C15 N16 C18 123.6(4) . . ?
C1 N10 C9 123.0(4) . . ?
C1 N10 C20 117.3(4) . . ?
C9 N10 C20 119.7(4) . . ?
C12 N13 C14 111.3(4) . . ?
C12 N13 C17 125.1(4) . . ?
C14 N13 C17 123.5(4) . . ?
O19 C1 N10 120.1(4) . . ?
O19 C1 C2 122.8(4) . . ?
N10 C1 C2 117.1(4) . . ?
C1 C2 H2 107.0 . . ?
C1 C2 C3 110.8(4) . . ?
C1 C2 B11 111.3(3) . . ?
C3 C2 H2 107.0 . . ?
C3 C2 B11 113.4(3) . . ?
B11 C2 H2 107.0 . . ?
N16 C12 N13 104.2(4) . . ?
N16 C12 B11 129.1(4) . . ?
N13 C12 B11 126.5(4) . . ?
C9 C4 C3 118.5(4) . . ?
C5 C4 C3 122.6(4) . . ?
C5 C4 C9 118.9(4) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 C2 110.6(3) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C4 C9 N10 118.9(4) . . ?
C4 C9 C8 120.0(4) . . ?
C8 C9 N10 121.1(4) . . ?
N16 C15 H15 126.3 . . ?
C14 C15 N16 107.4(4) . . ?
C14 C15 H15 126.3 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.2(5) . . ?
C6 C5 H5 119.4 . . ?
C9 C8 H8 120.2 . . ?
C7 C8 C9 119.7(5) . . ?
C7 C8 H8 120.2 . . ?
N13 C14 H14 126.9 . . ?
C15 C14 N13 106.2(4) . . ?
C15 C14 H14 126.9 . . ?
N16 C18 H18A 109.5 . . ?
N16 C18 H18B 109.5 . . ?
N16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N10 C20 H20A 109.5 . . ?
N10 C20 H20B 109.5 . . ?
N10 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 C7 H7 119.6 . . ?
C6 C7 C8 120.8(4) . . ?
C6 C7 H7 119.6 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.5(5) . . ?
C7 C6 H6 120.2 . . ?
N13 C17 H17A 109.5 . . ?
N13 C17 H17B 109.5 . . ?
N13 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 B11 H11A 112(2) . . ?
C2 B11 H11B 106(3) . . ?
C12 B11 C2 106.9(4) . . ?
C12 B11 H11A 108(2) . . ?
C12 B11 H11B 112(3) . . ?
H11A B11 H11B 110(3) . . ?

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
O19 C1 C2 C3 144.6(4) . . . . ?
O19 C1 C2 B11 -88.3(5) . . . . ?
N16 C12 B11 C2 93.0(5) . . . . ?
N16 C15 C14 N13 1.3(5) . . . . ?
N10 C1 C2 C3 -36.4(5) . . . . ?
N10 C1 C2 B11 90.8(5) . . . . ?
N10 C9 C8 C7 -176.0(5) . . . . ?
N13 C12 B11 C2 -80.1(5) . . . . ?
C1 N10 C9 C4 19.2(6) . . . . ?
C1 N10 C9 C8 -163.3(5) . . . . ?
C1 C2 C3 C4 51.8(5) . . . . ?
C1 C2 B11 C12 171.6(4) . . . . ?
C12 N16 C15 C14 -1.2(5) . . . . ?
C12 N13 C14 C15 -0.9(6) . . . . ?
C4 C9 C8 C7 1.4(8) . . . . ?
C4 C5 C6 C7 -0.5(9) . . . . ?
C3 C2 B11 C12 -62.7(4) . . . . ?
C3 C4 C9 N10 -0.2(6) . . . . ?
C3 C4 C9 C8 -177.7(4) . . . . ?
C3 C4 C5 C6 177.1(5) . . . . ?
C9 N10 C1 O19 -180.0(4) . . . . ?
C9 N10 C1 C2 1.0(6) . . . . ?
C9 C4 C3 C2 -34.6(5) . . . . ?
C9 C4 C5 C6 0.4(7) . . . . ?
C9 C8 C7 C6 -1.4(8) . . . . ?
C15 N16 C12 N13 0.6(5) . . . . ?
C15 N16 C12 B11 -173.7(5) . . . . ?
C5 C4 C3 C2 148.7(4) . . . . ?
C5 C4 C9 N10 176.6(4) . . . . ?
C5 C4 C9 C8 -0.8(7) . . . . ?
C8 C7 C6 C5 1.0(9) . . . . ?
C14 N13 C12 N16 0.2(5) . . . . ?
C14 N13 C12 B11 174.7(4) . . . . ?
C18 N16 C12 N13 -179.6(4) . . . . ?
C18 N16 C12 B11 6.1(8) . . . . ?
C18 N16 C15 C14 179.0(4) . . . . ?
C20 N10 C1 O19 0.3(6) . . . . ?
C20 N10 C1 C2 -178.8(4) . . . . ?
C20 N10 C9 C4 -161.0(4) . . . . ?
C20 N10 C9 C8 16.4(7) . . . . ?
C17 N13 C12 N16 177.3(5) . . . . ?
C17 N13 C12 B11 -8.2(8) . . . . ?
C17 N13 C14 C15 -178.1(5) . . . . ?
B11 C2 C3 C4 -74.3(4) . . . . ?

_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 1.265
_oxdiff_exptl_absorpt_empirical_full_min 0.642
####################################################################### 
# 
# 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_20210628-myq
_database_code_depnum_ccdc_archive 'CCDC 2151732'
loop_
_audit_author_name
_audit_author_address
abc
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2022-02-13 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2021-11-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 B N2 O2'
_chemical_formula_sum            'C16 H21 B N2 O2'
_chemical_formula_weight         284.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 B1 O1'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0836(6)
_cell_length_b                   9.1558(8)
_cell_length_c                   11.0863(8)
_cell_angle_alpha                114.228(8)
_cell_angle_beta                 106.840(6)
_cell_angle_gamma                93.503(6)
_cell_volume                     787.46(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2568
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3540
_cell_measurement_theta_min      5.1990
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5210
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.566
_diffrn_reflns_theta_min         4.662
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  25.00   1.00    1.00    --  -35.75  57.00 168.00   40
  2  ω    -99.00 -55.00   1.00    1.00    --  -35.75 -57.00  26.00   44
  3  ω     21.00  83.00   1.00    1.00    --   35.75  57.00 168.00   62
  4  ω      9.00  35.00   1.00    1.00    --   35.75 -57.00  26.00   26
  5  ω    123.00 173.00   1.00    2.19    --  107.12  57.00 168.00   50
  6  ω     57.00  84.00   1.00    2.19    --  107.12 -57.00  26.00   27
  7  ω   -108.00 -37.00   1.00    1.00    --  -35.75-178.00 -30.00   71
  8  ω     37.00  70.00   1.00    1.00    --   35.75 -99.00-180.00   33
  9  ω     22.00  75.00   1.00    1.00    --   35.75 -99.00 -30.00   53
 10  ω      6.00 107.00   1.00    1.00    --   35.75  19.00  30.00  101
 11  ω     20.00 103.00   1.00    1.00    --   35.75  57.00 -90.00   83
 12  ω     58.00 107.00   1.00    1.00    --   35.75 178.00 -30.00   49
 13  ω    104.00 148.00   1.00    2.19    --  107.12  61.00 150.00   44
 14  ω     39.00 125.00   1.00    2.19    --  107.12 -45.00  60.00   86
 15  ω     58.00 149.00   1.00    2.19    --  107.12 178.00 -60.00   91
 16  ω     62.00  88.00   1.00    2.19    --  107.12 -95.00  60.00   26
 17  ω     51.00 110.00   1.00    2.19    --  107.12-111.00 -30.00   59
 18  ω     52.00 109.00   1.00    2.19    --  107.12 -95.00   0.00   57
 19  ω     55.00  89.00   1.00    2.19    --  107.12 -95.00-120.00   34
 20  ω     40.00 124.00   1.00    2.19    --  107.12 -45.00 -60.00   84
 21  ω     92.00 149.00   1.00    2.19    --  107.12  45.00 -60.00   57
 22  ω     61.00 113.00   1.00    2.19    --  107.12-111.00 150.00   52
 23  ω     81.00 122.00   1.00    2.19    --  107.12  77.00-150.00   41
 24  ω     90.00 161.00   1.00    2.19    --  107.12  30.00  90.00   71
 25  ω    113.00 151.00   1.00    2.19    --  107.12 111.00  90.00   38
 26  ω    106.00 160.00   1.00    2.19    --  107.12 111.00  30.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0750863000
_diffrn_orient_matrix_UB_12      -0.1441454000
_diffrn_orient_matrix_UB_13      0.0151414000
_diffrn_orient_matrix_UB_21      0.0619577000
_diffrn_orient_matrix_UB_22      -0.1192512000
_diffrn_orient_matrix_UB_23      -0.1098749000
_diffrn_orient_matrix_UB_31      0.1526954000
_diffrn_orient_matrix_UB_32      0.0236170000
_diffrn_orient_matrix_UB_33      0.1186285000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                2347
_reflns_number_total             2990
_reflns_odcompleteness_completeness 99.89
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2990
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0668P)²+0.2016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1538
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C15(H15), C14(H14)
2.d Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C20(H20a,H20b,H20c), C18(H18a,H18b,H18c), C17(H17a,H17b,
 H17c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O10 O 0.30814(15) 0.59113(16) 0.78691(15) 0.0511(4) Uani 1 1 d . . . . .
O19 O 0.13415(17) 0.3764(2) 0.72775(18) 0.0667(5) Uani 1 1 d . . . . .
N16 N 0.1319(2) 0.2874(3) 0.3927(2) 0.0663(5) Uani 1 1 d . . . . .
N13 N 0.1352(2) 0.0531(3) 0.3927(2) 0.0667(6) Uani 1 1 d . . . . .
C6 C 0.5885(2) 0.5954(2) 0.85700(18) 0.0397(4) Uani 1 1 d . . . . .
C1 C 0.4634(2) 0.6668(2) 0.82296(19) 0.0420(4) Uani 1 1 d . . . . .
C5 C 0.7395(2) 0.6866(2) 0.90283(19) 0.0442(4) Uani 1 1 d . . . . .
C9 C 0.2701(2) 0.4271(2) 0.7500(2) 0.0478(4) Uani 1 1 d . . . . .
C8 C 0.3918(2) 0.3307(2) 0.7302(2) 0.0477(5) Uani 1 1 d . . . . .
H8 H 0.363775 0.231188 0.738805 0.057 Uiso 1 1 calc R U . . .
C3 C 0.6314(3) 0.9080(2) 0.8673(2) 0.0498(5) Uani 1 1 d . . . . .
C4 C 0.7578(2) 0.8406(2) 0.9071(2) 0.0506(5) Uani 1 1 d . . . . .
H4 H 0.858952 0.900572 0.937831 0.061 Uiso 1 1 calc R U . . .
C7 C 0.5559(2) 0.4229(2) 0.8382(2) 0.0482(5) Uani 1 1 d . . . . .
H7A H 0.563215 0.425038 0.927994 0.058 Uiso 1 1 calc R U . . .
H7B H 0.634310 0.366068 0.806774 0.058 Uiso 1 1 calc R U . . .
C2 C 0.4822(2) 0.8190(2) 0.8260(2) 0.0498(5) Uani 1 1 d . . . . .
H2 H 0.394634 0.861691 0.800262 0.060 Uiso 1 1 calc R U . . .
C12 C 0.2218(2) 0.2057(3) 0.4515(2) 0.0550(5) Uani 1 1 d . . . . .
C21 C 0.8815(2) 0.6189(3) 0.9470(3) 0.0624(6) Uani 1 1 d . . . . .
H21A H 0.878893 0.594666 1.022879 0.094 Uiso 1 1 calc R U . . .
H21B H 0.975224 0.698218 0.977707 0.094 Uiso 1 1 calc R U . . .
H21C H 0.881010 0.520545 0.868497 0.094 Uiso 1 1 calc R U . . .
C15 C -0.0101(3) 0.1851(5) 0.2974(3) 0.0881(10) Uani 1 1 d . . . . .
H15 H -0.092249 0.212531 0.243513 0.106 Uiso 1 1 calc R U . . .
C20 C 0.6538(3) 1.0720(3) 0.8666(3) 0.0759(7) Uani 1 1 d . . . . .
H20A H 0.764087 1.117775 0.900532 0.114 Uiso 1 1 calc R U . . .
H20B H 0.605031 1.144253 0.926645 0.114 Uiso 1 1 calc R U . . .
H20C H 0.606535 1.058624 0.772268 0.114 Uiso 1 1 calc R U . . .
C14 C -0.0074(3) 0.0401(5) 0.2972(3) 0.0912(10) Uani 1 1 d . . . . .
H14 H -0.087155 -0.053061 0.242584 0.109 Uiso 1 1 calc R U . . .
B11 B 0.3949(3) 0.2761(3) 0.5673(3) 0.0528(6) Uani 1 1 d . . . . .
C18 C 0.1770(4) 0.4574(4) 0.4228(3) 0.0850(8) Uani 1 1 d . . . . .
H18A H 0.199817 0.526648 0.521245 0.127 Uiso 1 1 calc R U . . .
H18B H 0.092297 0.486915 0.368103 0.127 Uiso 1 1 calc R U . . .
H18C H 0.268645 0.470839 0.398752 0.127 Uiso 1 1 calc R U . . .
C17 C 0.1844(3) -0.0787(3) 0.4251(3) 0.0870(9) Uani 1 1 d . . . . .
H17A H 0.291765 -0.079693 0.430721 0.130 Uiso 1 1 calc R U . . .
H17B H 0.118767 -0.181391 0.352155 0.130 Uiso 1 1 calc R U . . .
H17C H 0.175119 -0.061936 0.513667 0.130 Uiso 1 1 calc R U . . .
H11A H 0.451(3) 0.383(3) 0.560(2) 0.060(6) Uiso 1 1 d . . . . .
H11B H 0.469(3) 0.181(3) 0.546(3) 0.068(7) 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
O10 C1 1.398(2) . ?
O10 C9 1.375(2) . ?
O19 C9 1.209(2) . ?
N16 C12 1.348(3) . ?
N16 C15 1.381(3) . ?
N16 C18 1.456(3) . ?
N13 C12 1.348(3) . ?
N13 C14 1.377(4) . ?
N13 C17 1.453(4) . ?
C6 C1 1.381(2) . ?
C6 C5 1.394(3) . ?
C6 C7 1.504(2) . ?
C1 C2 1.379(2) . ?
C5 C4 1.390(3) . ?
C5 C21 1.507(3) . ?
C9 C8 1.466(3) . ?
C8 H8 0.9800 . ?
C8 C7 1.533(3) . ?
C8 B11 1.675(3) . ?
C3 C4 1.382(3) . ?
C3 C2 1.382(3) . ?
C3 C20 1.506(3) . ?
C4 H4 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C2 H2 0.9300 . ?
C12 B11 1.601(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C14 1.328(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C14 H14 0.9300 . ?
B11 H11A 1.12(2) . ?
B11 H11B 1.12(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C9 O10 C1 120.54(14) . . ?
C12 N16 C15 109.9(3) . . ?
C12 N16 C18 125.6(2) . . ?
C15 N16 C18 124.5(3) . . ?
C12 N13 C14 110.0(3) . . ?
C12 N13 C17 125.2(2) . . ?
C14 N13 C17 124.8(3) . . ?
C1 C6 C5 117.57(16) . . ?
C1 C6 C7 118.94(17) . . ?
C5 C6 C7 123.45(16) . . ?
C6 C1 O10 121.97(16) . . ?
C2 C1 O10 115.22(16) . . ?
C2 C1 C6 122.78(17) . . ?
C6 C5 C21 120.44(17) . . ?
C4 C5 C6 119.34(17) . . ?
C4 C5 C21 120.21(18) . . ?
O10 C9 C8 117.87(16) . . ?
O19 C9 O10 114.91(19) . . ?
O19 C9 C8 127.00(19) . . ?
C9 C8 H8 108.5 . . ?
C9 C8 C7 113.11(17) . . ?
C9 C8 B11 108.62(16) . . ?
C7 C8 H8 108.5 . . ?
C7 C8 B11 109.51(17) . . ?
B11 C8 H8 108.5 . . ?
C4 C3 C20 121.6(2) . . ?
C2 C3 C4 117.84(18) . . ?
C2 C3 C20 120.5(2) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 C5 122.48(19) . . ?
C3 C4 H4 118.8 . . ?
C6 C7 C8 110.97(15) . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C1 C2 C3 119.90(18) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
N16 C12 B11 127.0(2) . . ?
N13 C12 N16 105.6(2) . . ?
N13 C12 B11 127.4(2) . . ?
C5 C21 H21A 109.5 . . ?
C5 C21 H21B 109.5 . . ?
C5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N16 C15 H15 126.4 . . ?
C14 C15 N16 107.2(3) . . ?
C14 C15 H15 126.4 . . ?
C3 C20 H20A 109.5 . . ?
C3 C20 H20B 109.5 . . ?
C3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N13 C14 H14 126.3 . . ?
C15 C14 N13 107.4(3) . . ?
C15 C14 H14 126.3 . . ?
C8 B11 H11A 110.9(12) . . ?
C8 B11 H11B 107.4(12) . . ?
C12 B11 C8 111.82(17) . . ?
C12 B11 H11A 108.5(11) . . ?
C12 B11 H11B 110.5(13) . . ?
H11A B11 H11B 107.7(16) . . ?
N16 C18 H18A 109.5 . . ?
N16 C18 H18B 109.5 . . ?
N16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N13 C17 H17A 109.5 . . ?
N13 C17 H17B 109.5 . . ?
N13 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O10 C1 C2 C3 176.73(17) . . . . ?
O10 C9 C8 C7 39.1(2) . . . . ?
O10 C9 C8 B11 -82.7(2) . . . . ?
O19 C9 C8 C7 -146.5(2) . . . . ?
O19 C9 C8 B11 91.7(2) . . . . ?
N16 C12 B11 C8 98.5(2) . . . . ?
N16 C15 C14 N13 0.4(3) . . . . ?
N13 C12 B11 C8 -81.2(3) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C6 C5 C4 C3 0.0(3) . . . . ?
C1 O10 C9 O19 176.44(17) . . . . ?
C1 O10 C9 C8 -8.5(3) . . . . ?
C1 C6 C5 C4 -2.5(3) . . . . ?
C1 C6 C5 C21 177.68(18) . . . . ?
C1 C6 C7 C8 22.9(2) . . . . ?
C5 C6 C1 O10 -174.75(16) . . . . ?
C5 C6 C1 C2 3.3(3) . . . . ?
C5 C6 C7 C8 -154.85(18) . . . . ?
C9 O10 C1 C6 -16.3(3) . . . . ?
C9 O10 C1 C2 165.56(17) . . . . ?
C9 C8 C7 C6 -44.8(2) . . . . ?
C9 C8 B11 C12 -46.6(2) . . . . ?
C4 C3 C2 C1 -1.2(3) . . . . ?
C7 C6 C1 O10 7.4(3) . . . . ?
C7 C6 C1 C2 -174.60(18) . . . . ?
C7 C6 C5 C4 175.27(18) . . . . ?
C7 C6 C5 C21 -4.6(3) . . . . ?
C7 C8 B11 C12 -170.62(17) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
C12 N16 C15 C14 -0.2(3) . . . . ?
C12 N13 C14 C15 -0.5(3) . . . . ?
C21 C5 C4 C3 179.8(2) . . . . ?
C15 N16 C12 N13 -0.1(2) . . . . ?
C15 N16 C12 B11 -179.9(2) . . . . ?
C20 C3 C4 C5 -177.3(2) . . . . ?
C20 C3 C2 C1 178.0(2) . . . . ?
C14 N13 C12 N16 0.4(2) . . . . ?
C14 N13 C12 B11 -179.8(2) . . . . ?
B11 C8 C7 C6 76.5(2) . . . . ?
C18 N16 C12 N13 -179.4(2) . . . . ?
C18 N16 C12 B11 0.9(4) . . . . ?
C18 N16 C15 C14 179.0(2) . . . . ?
C17 N13 C12 N16 -179.5(2) . . . . ?
C17 N13 C12 B11 0.2(4) . . . . ?
C17 N13 C14 C15 179.4(2) . . . . ?

_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 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.673
