# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_95z
_audit_block_doi                 10.5517/ccdc.csd.cc2g18ng
_database_code_depnum_ccdc_archive 'CCDC 2265345'
loop_
_audit_author_name
_audit_author_address
'Jiuzhong Huang'
;Gannan Medical University
China
;
_audit_update_record             
;
2023-05-25 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_audit_creation_date             2022-12-07
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 B F N O2'
_chemical_formula_sum            'C22 H23 B F N O2'
_chemical_formula_weight         363.22
_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'
F F 0.0171 0.0103 '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      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                   9.8733(9)
_cell_length_b                   11.5417(10)
_cell_length_c                   17.0581(17)
_cell_angle_alpha                90
_cell_angle_beta                 95.130(9)
_cell_angle_gamma                90
_cell_volume                     1936.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3402
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      28.6150
_cell_measurement_theta_min      2.7320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light black'
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8907
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.133
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  16.00   1.00    2.00    --  -11.43 -99.00  30.00   26
  2  ω    -61.00  33.00   1.00    2.00    --   12.05 -38.00-120.00   94
  3  ω    -12.00  76.00   1.00    2.00    --   12.05  38.00  60.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0312511000
_diffrn_orient_matrix_UB_12      -0.0516664000
_diffrn_orient_matrix_UB_13      -0.0152039000
_diffrn_orient_matrix_UB_21      -0.0146306000
_diffrn_orient_matrix_UB_22      -0.0161468000
_diffrn_orient_matrix_UB_23      0.0385004000
_diffrn_orient_matrix_UB_31      -0.0632907000
_diffrn_orient_matrix_UB_32      0.0290909000
_diffrn_orient_matrix_UB_33      -0.0055749000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2718
_reflns_number_total             3417
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.045
_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)+(0.0508P)²+0.6104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1198
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_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
F1 F 0.90228(14) 0.52439(14) 0.25328(10) 0.0846(5) Uani 1 1 d . . . . .
O1 O 0.36850(13) 0.44750(10) 0.38161(7) 0.0366(3) Uani 1 1 d . . . . .
O2 O 0.31332(15) 0.57684(10) 0.28456(7) 0.0455(4) Uani 1 1 d . . . . .
N1 N 0.66257(15) 0.85364(14) 0.49354(10) 0.0463(4) Uani 1 1 d . . . . .
H1A H 0.704997 0.841731 0.451991 0.056 Uiso 1 1 d R U . . .
H1B H 0.659739 0.927495 0.502264 0.056 Uiso 1 1 d R U . . .
C1 C 0.29473(18) 0.80769(15) 0.51148(10) 0.0328(4) Uani 1 1 d . . . . .
C2 C 0.1850(2) 0.85471(17) 0.54972(11) 0.0443(5) Uani 1 1 d . . . . .
H2 H 0.200833 0.918583 0.584462 0.053 Uiso 1 1 calc R U . . .
C3 C 0.0576(2) 0.80946(19) 0.53724(13) 0.0538(6) Uani 1 1 d . . . . .
H3 H -0.014606 0.842729 0.562836 0.065 Uiso 1 1 calc R U . . .
C4 C 0.0319(2) 0.71459(19) 0.48720(13) 0.0502(5) Uani 1 1 d . . . . .
H4 H -0.057350 0.683479 0.479097 0.060 Uiso 1 1 calc R U . . .
C5 C 0.13506(18) 0.66670(16) 0.44999(11) 0.0389(5) Uani 1 1 d . . . . .
H5 H 0.116624 0.602095 0.416203 0.047 Uiso 1 1 calc R U . . .
C6 C 0.26886(17) 0.71124(14) 0.46067(9) 0.0293(4) Uani 1 1 d . . . . .
C7 C 0.37740(16) 0.66386(14) 0.42069(9) 0.0277(4) Uani 1 1 d . . . . .
C8 C 0.50532(17) 0.71285(14) 0.43095(9) 0.0289(4) Uani 1 1 d . . . . .
C9 C 0.53053(17) 0.81008(15) 0.48183(10) 0.0325(4) Uani 1 1 d . . . . .
C10 C 0.42718(18) 0.85451(15) 0.52102(10) 0.0353(4) Uani 1 1 d . . . . .
H10 H 0.445066 0.918433 0.555486 0.042 Uiso 1 1 calc R U . . .
C11 C 0.61662(16) 0.66535(14) 0.38648(10) 0.0310(4) Uani 1 1 d . . . . .
C12 C 0.67831(19) 0.56056(16) 0.40786(12) 0.0411(5) Uani 1 1 d . . . . .
H12 H 0.653392 0.520843 0.453190 0.049 Uiso 1 1 calc R U . . .
C13 C 0.7760(2) 0.51323(19) 0.36372(14) 0.0521(6) Uani 1 1 d . . . . .
H13 H 0.818586 0.441665 0.378342 0.063 Uiso 1 1 calc R U . . .
C14 C 0.80940(19) 0.5722(2) 0.29865(14) 0.0531(6) Uani 1 1 d . . . . .
C15 C 0.7532(2) 0.67596(19) 0.27592(13) 0.0507(5) Uani 1 1 d . . . . .
H15 H 0.779579 0.715140 0.230731 0.061 Uiso 1 1 calc R U . . .
C16 C 0.65643(18) 0.72261(16) 0.32073(11) 0.0400(5) Uani 1 1 d . . . . .
H16 H 0.616472 0.795252 0.306198 0.048 Uiso 1 1 calc R U . . .
C17 C 0.32028(17) 0.37786(14) 0.31278(10) 0.0300(4) Uani 1 1 d . . . . .
C19 C 0.4138(2) 0.27555(16) 0.30746(12) 0.0468(5) Uani 1 1 d . . . . .
H19A H 0.508241 0.302489 0.310567 0.070 Uiso 1 1 calc R U . . .
H19B H 0.391714 0.235426 0.257313 0.070 Uiso 1 1 calc R U . . .
H19C H 0.402216 0.222179 0.351047 0.070 Uiso 1 1 calc R U . . .
C20 C 0.1787(2) 0.33719(19) 0.32738(14) 0.0545(6) Uani 1 1 d . . . . .
H20A H 0.182024 0.296925 0.378094 0.082 Uiso 1 1 calc R U . . .
H20B H 0.144716 0.284165 0.285254 0.082 Uiso 1 1 calc R U . . .
H20C H 0.117886 0.404188 0.328221 0.082 Uiso 1 1 calc R U . . .
C21 C 0.3237(2) 0.46551(15) 0.24427(10) 0.0364(4) Uani 1 1 d . . . . .
C22 C 0.4585(3) 0.4671(2) 0.20772(14) 0.0640(7) Uani 1 1 d . . . . .
H22A H 0.461081 0.533918 0.172413 0.096 Uiso 1 1 calc R U . . .
H22B H 0.468226 0.395592 0.177782 0.096 Uiso 1 1 calc R U . . .
H22C H 0.533262 0.472913 0.249404 0.096 Uiso 1 1 calc R U . . .
C23 C 0.2061(2) 0.45618(19) 0.18150(12) 0.0590(6) Uani 1 1 d . . . . .
H23A H 0.120419 0.467206 0.205405 0.089 Uiso 1 1 calc R U . . .
H23B H 0.206725 0.379423 0.156972 0.089 Uiso 1 1 calc R U . . .
H23C H 0.214999 0.515871 0.141420 0.089 Uiso 1 1 calc R U . . .
B1 B 0.35262(18) 0.56024(16) 0.36147(11) 0.0267(4) 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
F1 C14 1.368(2) . ?
O1 C17 1.4666(19) . ?
O1 B1 1.351(2) . ?
O2 C21 1.465(2) . ?
O2 B1 1.348(2) . ?
N1 H1A 0.8659 . ?
N1 H1B 0.8662 . ?
N1 C9 1.395(2) . ?
C1 C2 1.421(3) . ?
C1 C6 1.420(2) . ?
C1 C10 1.411(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.361(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.364(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.414(2) . ?
C6 C7 1.429(2) . ?
C7 C8 1.381(2) . ?
C7 B1 1.571(2) . ?
C8 C9 1.427(2) . ?
C8 C11 1.494(2) . ?
C9 C10 1.369(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(2) . ?
C11 C16 1.388(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.367(3) . ?
C14 C15 1.361(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(3) . ?
C16 H16 0.9500 . ?
C17 C19 1.507(2) . ?
C17 C20 1.516(2) . ?
C17 C21 1.548(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.519(3) . ?
C21 C23 1.511(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
B1 O1 C17 107.59(13) . . ?
B1 O2 C21 107.80(13) . . ?
H1A N1 H1B 108.8 . . ?
C9 N1 H1A 109.9 . . ?
C9 N1 H1B 109.6 . . ?
C6 C1 C2 118.47(16) . . ?
C10 C1 C2 122.51(17) . . ?
C10 C1 C6 119.01(16) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.89(18) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.75(19) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.93(19) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.37(18) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 119.31(15) . . ?
C5 C6 C1 118.60(16) . . ?
C5 C6 C7 122.08(15) . . ?
C6 C7 B1 121.20(14) . . ?
C8 C7 C6 119.95(15) . . ?
C8 C7 B1 118.78(15) . . ?
C7 C8 C9 120.47(16) . . ?
C7 C8 C11 119.43(15) . . ?
C9 C8 C11 120.08(15) . . ?
N1 C9 C8 118.72(16) . . ?
C10 C9 N1 121.54(16) . . ?
C10 C9 C8 119.65(16) . . ?
C1 C10 H10 119.2 . . ?
C9 C10 C1 121.60(16) . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C8 120.77(16) . . ?
C16 C11 C8 120.64(15) . . ?
C16 C11 C12 118.53(17) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.69(19) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.8 . . ?
C14 C13 C12 118.32(19) . . ?
C14 C13 H13 120.8 . . ?
C13 C14 F1 118.8(2) . . ?
C15 C14 F1 118.1(2) . . ?
C15 C14 C13 123.18(19) . . ?
C14 C15 H15 121.0 . . ?
C14 C15 C16 117.9(2) . . ?
C16 C15 H15 121.0 . . ?
C11 C16 H16 119.3 . . ?
C15 C16 C11 121.32(18) . . ?
C15 C16 H16 119.3 . . ?
O1 C17 C19 108.72(14) . . ?
O1 C17 C20 106.04(14) . . ?
O1 C17 C21 102.63(12) . . ?
C19 C17 C20 110.25(16) . . ?
C19 C17 C21 114.31(15) . . ?
C20 C17 C21 114.15(16) . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 C17 102.22(13) . . ?
O2 C21 C22 106.41(15) . . ?
O2 C21 C23 108.24(15) . . ?
C22 C21 C17 113.39(16) . . ?
C23 C21 C17 114.89(16) . . ?
C23 C21 C22 110.85(17) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 B1 C7 124.19(15) . . ?
O2 B1 O1 113.64(15) . . ?
O2 B1 C7 122.17(15) . . ?

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
F1 C14 C15 C16 178.24(18) . . . . ?
O1 C17 C21 O2 -24.03(16) . . . . ?
O1 C17 C21 C22 90.09(17) . . . . ?
O1 C17 C21 C23 -141.00(15) . . . . ?
N1 C9 C10 C1 -177.57(16) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C1 C6 C7 C8 -0.8(2) . . . . ?
C1 C6 C7 B1 -177.67(15) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C2 C1 C6 C7 179.01(15) . . . . ?
C2 C1 C10 C9 -178.02(17) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 -178.47(17) . . . . ?
C5 C6 C7 C8 177.77(15) . . . . ?
C5 C6 C7 B1 0.9(2) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C6 C1 C10 C9 0.8(3) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C6 C7 C8 C11 -177.69(14) . . . . ?
C6 C7 B1 O1 -92.5(2) . . . . ?
C6 C7 B1 O2 87.7(2) . . . . ?
C7 C8 C9 N1 176.99(15) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
C7 C8 C11 C12 -74.5(2) . . . . ?
C7 C8 C11 C16 102.64(19) . . . . ?
C8 C7 B1 O1 90.6(2) . . . . ?
C8 C7 B1 O2 -89.2(2) . . . . ?
C8 C9 C10 C1 -1.1(3) . . . . ?
C8 C11 C12 C13 176.16(17) . . . . ?
C8 C11 C16 C15 -175.78(17) . . . . ?
C9 C8 C11 C12 107.25(19) . . . . ?
C9 C8 C11 C16 -75.6(2) . . . . ?
C10 C1 C2 C3 177.97(19) . . . . ?
C10 C1 C6 C5 -178.47(16) . . . . ?
C10 C1 C6 C7 0.2(2) . . . . ?
C11 C8 C9 N1 -4.8(2) . . . . ?
C11 C8 C9 C10 178.61(15) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C11 C16 C15 1.4(3) . . . . ?
C12 C13 C14 F1 -177.86(18) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C16 C11 C12 C13 -1.0(3) . . . . ?
C17 O1 B1 O2 -6.9(2) . . . . ?
C17 O1 B1 C7 173.30(15) . . . . ?
C19 C17 C21 O2 -141.55(15) . . . . ?
C19 C17 C21 C22 -27.4(2) . . . . ?
C19 C17 C21 C23 101.47(19) . . . . ?
C20 C17 C21 O2 90.22(17) . . . . ?
C20 C17 C21 C22 -155.66(17) . . . . ?
C20 C17 C21 C23 -26.8(2) . . . . ?
C21 O2 B1 O1 -9.9(2) . . . . ?
C21 O2 B1 C7 169.88(15) . . . . ?
B1 O1 C17 C19 140.85(15) . . . . ?
B1 O1 C17 C20 -100.61(16) . . . . ?
B1 O1 C17 C21 19.43(17) . . . . ?
B1 O2 C21 C17 21.09(18) . . . . ?
B1 O2 C21 C22 -98.07(18) . . . . ?
B1 O2 C21 C23 142.74(17) . . . . ?
B1 C7 C8 C9 177.49(15) . . . . ?
B1 C7 C8 C11 -0.7(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 1.839
_oxdiff_exptl_absorpt_empirical_full_min 0.693
####################################################################### 
# 
# 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_99-1
_audit_block_doi                 10.5517/ccdc.csd.cc2g18ph
_database_code_depnum_ccdc_archive 'CCDC 2265346'
loop_
_audit_author_name
_audit_author_address
'Jiuzhong Huang'
;Gannan Medical University
China
;
_audit_update_record             
;
2023-05-25 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_audit_creation_date             2022-10-07
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H26 B N O2'
_chemical_formula_sum            'C23 H26 B N O2'
_chemical_formula_weight         359.26
_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 0.0181 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                   7.0732(3)
_cell_length_b                   12.8154(5)
_cell_length_c                   12.8838(5)
_cell_angle_alpha                109.101(4)
_cell_angle_beta                 103.862(4)
_cell_angle_gamma                102.475(4)
_cell_volume                     1014.75(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6404
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      71.4160
_cell_measurement_theta_min      3.8450
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10644
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.598
_diffrn_reflns_theta_min         3.854
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     82.00 123.00   0.50    0.63    --   42.30  77.00 -30.00   82
  2  ω    -46.00  45.00   0.50    0.63    --   42.30 -77.00-180.00  182
  3  ω     86.00 127.00   0.50    0.63    --   42.30  77.00  30.00   82
  4  ω     91.00 117.00   0.50    0.63    --   42.30  77.00  90.00   52
  5  ω    -33.00  77.00   0.50    0.63    --   42.30 -82.00 -60.00  220
  6  ω     15.00 134.00   0.50    0.50    --  101.60 -64.00 -30.00  238
  7  ω     79.00 141.00   0.50    0.50    --  101.60 -77.00 120.00  124
  8  ω     34.00  98.00   0.50    0.50    --  101.60 -64.00 150.00  128
  9  ω    146.00 179.00   0.50    0.50    --  101.60  82.00   0.00   66
 10  ω     87.00 115.00   0.50    0.50    --  101.60  82.00   0.00   56
 11  ω     87.00 191.00   0.50    0.50    --  101.60  82.00 -90.00  208
 12  ω     87.00 126.00   0.50    0.50    --  101.60  82.00-120.00   78
 13  ω     99.00 126.00   0.50    0.50    --  101.60  50.00  60.00   54
 14  ω    150.00 183.00   0.50    0.50    --  101.60  50.00  60.00   66
 15  ω    105.00 131.00   0.50    0.50    --  101.60 -64.00 150.00   52
 16  ω    153.00 178.00   0.50    0.50    --  101.60 -25.00  90.00   50
 17  ω     38.00 124.00   0.50    0.50    --  101.60 -25.00  90.00  172
 18  ω     43.00  69.00   0.50    0.63    --   42.30  57.00-150.00   52
 19  ω     90.00 116.00   0.50    0.63    --   42.30  77.00-120.00   52
 20  ω     85.00 112.00   0.50    0.63    --   42.30  57.00-150.00   54
 21  ω    100.00 126.00   0.50    0.50    --  101.60 -50.00 150.00   52
 22  ω     42.00  68.00   0.50    0.50    --  101.60 -50.00 150.00   52
 23  ω    102.00 128.00   0.50    0.50    --  101.60 -12.00 -30.00   52
 24  ω     45.00  80.00   0.50    0.50    --  101.60 -12.00 -30.00   70
 25  ω    -20.00  71.00   0.50    0.50    --   42.30 -57.00  30.00  182
 26  ω     16.00  82.00   0.50    0.50    --   42.30 -82.00  30.00  132
 27  ω     50.00  76.00   0.50    0.50    --   42.30 -82.00-120.00   52
 28  ω     -4.00  27.00   0.50    0.50    --   42.30 -82.00-120.00   62
 29  ω     65.00 101.00   0.50    0.50    --  101.60 -82.00 120.00   72
 30  ω     14.00  40.00   0.50    0.50    --  101.60 -12.00  30.00   52
 31  ω     83.00 138.00   0.50    0.50    --  101.60 -82.00-180.00  110
 32  ω     82.00 108.00   0.50    0.50    --  101.60 -82.00   0.00   52
 33  ω     13.00  40.00   0.50    0.50    --  101.60 -82.00 120.00   54
 34  ω     64.00 110.00   0.50    0.50    --  101.60 -82.00-120.00   92
 35  ω     94.00 180.00   0.50    0.50    --  101.60 -12.00  30.00  172
 36  ω     73.00 109.00   0.50    0.50    --  101.60 -82.00  60.00   72
 37  ω     70.00 100.00   0.50    0.50    --  101.60  50.00 150.00   60
 38  ω    149.00 175.00   0.50    0.50    --  101.60  50.00 150.00   52
 39  ω     57.00 105.00   0.50    0.50    --  101.60 -50.00-150.00   96
 40  ω     64.00  90.00   0.50    0.50    --  101.60 -12.00  30.00   52
 41  ω     12.00 143.00   0.50    0.50    --  101.60 -82.00 -30.00  262
 42  ω    148.00 175.00   0.50    0.50    --  101.60  50.00-180.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0495798000
_diffrn_orient_matrix_UB_12      -0.1044082000
_diffrn_orient_matrix_UB_13      0.0205444000
_diffrn_orient_matrix_UB_21      0.1031566000
_diffrn_orient_matrix_UB_22      0.0763793000
_diffrn_orient_matrix_UB_23      0.1314269000
_diffrn_orient_matrix_UB_31      -0.2073923000
_diffrn_orient_matrix_UB_32      -0.0362495000
_diffrn_orient_matrix_UB_33      0.0186915000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3460
_reflns_number_total             3847
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3847
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0838
_refine_ls_restrained_S_all      1.037
_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)+(0.1384P)²+0.6023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2317
_refine_ls_wR_factor_ref         0.2377
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C)
;
_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
O1 O 0.3731(2) 0.72155(15) 0.30405(15) 0.0460(5) Uani 1 1 d . . . . .
O2 O 0.6289(2) 0.65768(16) 0.37707(17) 0.0493(5) Uani 1 1 d . . . . .
N1 N 0.0086(4) 0.0116(2) 0.2362(2) 0.0678(7) Uani 1 1 d . . . . .
C1 C 0.1096(3) 0.40052(19) 0.23916(18) 0.0339(5) Uani 1 1 d . . . . .
C2 C 0.0956(3) 0.4406(2) 0.1501(2) 0.0418(5) Uani 1 1 d . . . . .
H2 H 0.116325 0.521124 0.168253 0.050 Uiso 1 1 calc R U . . .
C3 C 0.0521(4) 0.3654(2) 0.0354(2) 0.0488(6) Uani 1 1 d . . . . .
H3 H 0.044060 0.394583 -0.023864 0.059 Uiso 1 1 calc R U . . .
C4 C 0.0205(4) 0.2478(2) 0.0079(2) 0.0490(6) Uani 1 1 d . . . . .
H4 H -0.007032 0.195992 -0.070100 0.059 Uiso 1 1 calc R U . . .
C5 C 0.0292(3) 0.2061(2) 0.0950(2) 0.0429(6) Uani 1 1 d . . . . .
H5 H 0.004878 0.125049 0.075515 0.051 Uiso 1 1 calc R U . . .
C6 C 0.0726(3) 0.2801(2) 0.21022(19) 0.0360(5) Uani 1 1 d . . . . .
C7 C 0.0870(3) 0.23585(19) 0.30654(19) 0.0397(5) Uani 1 1 d . . . . .
H7A H 0.227182 0.274929 0.364762 0.048 Uiso 1 1 calc R U . . .
H7B H -0.010773 0.258226 0.346173 0.048 Uiso 1 1 calc R U . . .
C8 C 0.0431(4) 0.1095(2) 0.2665(2) 0.0486(6) Uani 1 1 d . . . . .
C9 C 0.1615(3) 0.48087(19) 0.36131(18) 0.0331(5) Uani 1 1 d . . . . .
H9 H 0.093637 0.452459 0.406663 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2944(3) 0.58994(18) 0.41547(17) 0.0316(5) Uani 1 1 d . . . . .
C11 C 0.3406(3) 0.65681(18) 0.54237(18) 0.0325(5) Uani 1 1 d . . . . .
C12 C 0.3502(3) 0.60222(19) 0.62047(19) 0.0344(5) Uani 1 1 d . . . . .
H12 H 0.319762 0.519981 0.591741 0.041 Uiso 1 1 calc R U . . .
C13 C 0.4033(3) 0.6660(2) 0.73877(19) 0.0394(5) Uani 1 1 d . . . . .
H13 H 0.407551 0.626507 0.789753 0.047 Uiso 1 1 calc R U . . .
C14 C 0.4506(3) 0.7868(2) 0.7850(2) 0.0416(5) Uani 1 1 d . . . . .
C15 C 0.4412(4) 0.8413(2) 0.7081(2) 0.0435(6) Uani 1 1 d . . . . .
H15 H 0.471751 0.923587 0.737431 0.052 Uiso 1 1 calc R U . . .
C16 C 0.3878(3) 0.77821(19) 0.5888(2) 0.0385(5) Uani 1 1 d . . . . .
H16 H 0.383327 0.818037 0.538126 0.046 Uiso 1 1 calc R U . . .
C17 C 0.5115(4) 0.8560(3) 0.9139(2) 0.0576(7) Uani 1 1 d . . . . .
H17A H 0.387929 0.860167 0.934674 0.086 Uiso 1 1 calc R U . . .
H17B H 0.600825 0.934909 0.934724 0.086 Uiso 1 1 calc R U . . .
H17C H 0.585292 0.817838 0.956516 0.086 Uiso 1 1 calc R U . . .
C18 C 0.5597(3) 0.7903(2) 0.2958(2) 0.0437(6) Uani 1 1 d . . . . .
C19 C 0.6376(5) 0.9092(3) 0.3967(3) 0.0654(8) Uani 1 1 d . . . . .
H19A H 0.529260 0.945728 0.393226 0.098 Uiso 1 1 calc R U . . .
H19B H 0.758381 0.958628 0.391257 0.098 Uiso 1 1 calc R U . . .
H19C H 0.675340 0.899895 0.470718 0.098 Uiso 1 1 calc R U . . .
C20 C 0.5041(4) 0.8065(3) 0.1842(3) 0.0641(9) Uani 1 1 d . . . . .
H20A H 0.445559 0.730148 0.118466 0.096 Uiso 1 1 calc R U . . .
H20B H 0.627504 0.852087 0.177432 0.096 Uiso 1 1 calc R U . . .
H20C H 0.402684 0.847890 0.183335 0.096 Uiso 1 1 calc R U . . .
C21 C 0.7059(4) 0.7188(2) 0.3103(3) 0.0502(6) Uani 1 1 d . . . . .
C22 C 0.9290(5) 0.7858(4) 0.3729(5) 0.0999(16) Uani 1 1 d . . . . .
H22A H 0.948340 0.838843 0.452101 0.150 Uiso 1 1 calc R U . . .
H22B H 0.978638 0.830930 0.330891 0.150 Uiso 1 1 calc R U . . .
H22C H 1.006356 0.731498 0.376937 0.150 Uiso 1 1 calc R U . . .
C23 C 0.6774(9) 0.6221(3) 0.1933(4) 0.1046(17) Uani 1 1 d . . . . .
H23A H 0.736996 0.563867 0.208099 0.157 Uiso 1 1 calc R U . . .
H23B H 0.746665 0.656132 0.149023 0.157 Uiso 1 1 calc R U . . .
H23C H 0.530457 0.584636 0.148332 0.157 Uiso 1 1 calc R U . . .
B1 B 0.4306(4) 0.6547(2) 0.3605(2) 0.0343(5) 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
O1 C18 1.467(3) . ?
O1 B1 1.358(3) . ?
O2 C21 1.460(3) . ?
O2 B1 1.357(3) . ?
N1 C8 1.134(3) . ?
C1 C2 1.394(3) . ?
C1 C6 1.412(3) . ?
C1 C9 1.473(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C6 C7 1.515(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.464(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.343(3) . ?
C10 C11 1.490(3) . ?
C10 B1 1.576(3) . ?
C11 C12 1.398(3) . ?
C11 C16 1.400(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.394(3) . ?
C14 C15 1.383(4) . ?
C14 C17 1.503(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.521(4) . ?
C18 C20 1.492(3) . ?
C18 C21 1.540(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.493(4) . ?
C21 C23 1.541(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
B1 O1 C18 107.12(17) . . ?
B1 O2 C21 107.20(17) . . ?
C2 C1 C6 118.5(2) . . ?
C2 C1 C9 121.5(2) . . ?
C6 C1 C9 119.98(19) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.5(2) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.5(2) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C7 118.85(19) . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 122.0(2) . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 C6 114.2(2) . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
N1 C8 C7 179.4(3) . . ?
C1 C9 H9 116.5 . . ?
C10 C9 C1 127.03(19) . . ?
C10 C9 H9 116.5 . . ?
C9 C10 C11 120.20(18) . . ?
C9 C10 B1 126.00(19) . . ?
C11 C10 B1 113.51(17) . . ?
C12 C11 C10 121.58(19) . . ?
C12 C11 C16 117.4(2) . . ?
C16 C11 C10 120.88(18) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.5(2) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C17 121.3(2) . . ?
C15 C14 C13 117.7(2) . . ?
C15 C14 C17 121.0(2) . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.4(2) . . ?
C16 C15 H15 119.3 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.9(2) . . ?
C15 C16 H16 119.6 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C18 C19 107.6(2) . . ?
O1 C18 C20 108.60(19) . . ?
O1 C18 C21 102.39(17) . . ?
C19 C18 C21 111.7(2) . . ?
C20 C18 C19 108.6(2) . . ?
C20 C18 C21 117.4(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 C18 102.79(18) . . ?
O2 C21 C22 109.4(2) . . ?
O2 C21 C23 105.2(2) . . ?
C18 C21 C23 112.0(3) . . ?
C22 C21 C18 116.8(3) . . ?
C22 C21 C23 109.8(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 B1 C10 124.9(2) . . ?
O2 B1 O1 113.49(19) . . ?
O2 B1 C10 121.31(19) . . ?

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
O1 C18 C21 O2 -25.9(2) . . . . ?
O1 C18 C21 C22 -145.7(3) . . . . ?
O1 C18 C21 C23 86.5(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C1 C6 C7 C8 179.26(19) . . . . ?
C1 C9 C10 C11 -175.63(18) . . . . ?
C1 C9 C10 B1 -2.2(3) . . . . ?
C2 C1 C6 C5 1.7(3) . . . . ?
C2 C1 C6 C7 -179.85(19) . . . . ?
C2 C1 C9 C10 -36.8(3) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C6 C7 -178.7(2) . . . . ?
C5 C6 C7 C8 -2.4(3) . . . . ?
C6 C1 C2 C3 -1.8(3) . . . . ?
C6 C1 C9 C10 143.2(2) . . . . ?
C9 C1 C2 C3 178.3(2) . . . . ?
C9 C1 C6 C5 -178.32(18) . . . . ?
C9 C1 C6 C7 0.1(3) . . . . ?
C9 C10 C11 C12 35.7(3) . . . . ?
C9 C10 C11 C16 -148.1(2) . . . . ?
C9 C10 B1 O1 90.6(3) . . . . ?
C9 C10 B1 O2 -96.6(3) . . . . ?
C10 C11 C12 C13 176.71(18) . . . . ?
C10 C11 C16 C15 -176.68(19) . . . . ?
C11 C10 B1 O1 -95.6(3) . . . . ?
C11 C10 B1 O2 77.2(3) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C11 C16 C15 -0.3(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C12 C13 C14 C17 -179.0(2) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
C17 C14 C15 C16 179.1(2) . . . . ?
C18 O1 B1 O2 -8.7(3) . . . . ?
C18 O1 B1 C10 164.6(2) . . . . ?
C19 C18 C21 O2 88.9(2) . . . . ?
C19 C18 C21 C22 -30.9(3) . . . . ?
C19 C18 C21 C23 -158.7(2) . . . . ?
C20 C18 C21 O2 -144.7(2) . . . . ?
C20 C18 C21 C22 95.5(3) . . . . ?
C20 C18 C21 C23 -32.3(3) . . . . ?
C21 O2 B1 O1 -9.2(3) . . . . ?
C21 O2 B1 C10 177.3(2) . . . . ?
B1 O1 C18 C19 -96.3(2) . . . . ?
B1 O1 C18 C20 146.4(2) . . . . ?
B1 O1 C18 C21 21.5(3) . . . . ?
B1 O2 C21 C18 21.9(3) . . . . ?
B1 O2 C21 C22 146.6(3) . . . . ?
B1 O2 C21 C23 -95.5(3) . . . . ?
B1 C10 C11 C12 -138.5(2) . . . . ?
B1 C10 C11 C16 37.7(3) . . . . ?

_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 3.430
_oxdiff_exptl_absorpt_empirical_full_min 0.259
####################################################################### 
# 
# 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_2822
_audit_block_doi                 10.5517/ccdc.csd.cc2g18rk
_database_code_depnum_ccdc_archive 'CCDC 2265348'
loop_
_audit_author_name
_audit_author_address
'Jiuzhong Huang'
;Gannan Medical University
China
;
_audit_update_record             
;
2023-05-25 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_audit_creation_date             2022-10-06
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H28 B N O2'
_chemical_formula_sum            'C20 H28 B N O2'
_chemical_formula_weight         325.24
_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 0.0181 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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.9832(5)
_cell_length_b                   9.6904(4)
_cell_length_c                   13.4858(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.376(3)
_cell_angle_gamma                90
_cell_volume                     1926.03(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5145
_cell_measurement_temperature    166(20)
_cell_measurement_theta_max      71.2190
_cell_measurement_theta_min      5.4340
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10323
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.355
_diffrn_reflns_theta_min         2.998
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      166(20)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     80.00 115.00   0.50    0.50    --   42.30  77.00  60.00   70
  2  ω    104.00 129.00   0.50    0.50    --   42.30  77.00 -60.00   50
  3  ω    -13.00  13.00   0.50    0.50    --   42.30 -82.00 -90.00   52
  4  ω     34.00  84.00   0.50    0.50    --   42.30  57.00-180.00  100
  5  ω     88.00 120.00   0.50    0.50    --   42.30  77.00 -30.00   64
  6  ω     92.00 132.00   0.50    0.50    --   42.30  77.00-180.00   80
  7  ω     83.00 119.00   0.50    0.50    --   42.30  77.00 120.00   72
  8  ω     44.00  86.00   0.50    0.50    --   42.30 -82.00 -90.00   84
  9  ω     81.00 127.00   0.50    0.50    --   42.30  77.00  30.00   92
 10  ω     88.00 191.00   0.50    1.00    --  101.60  82.00-120.00  206
 11  ω     46.00 131.00   0.50    1.00    --  101.60 -50.00 120.00  170
 12  ω     87.00 144.00   0.50    1.00    --  101.60  82.00   0.00  114
 13  ω     82.00 154.00   0.50    1.00    --  101.60  64.00 -30.00  144
 14  ω    134.00 169.00   0.50    1.00    --  101.60  82.00 -30.00   70
 15  ω     70.00 146.00   0.50    1.00    --  101.60  50.00 -30.00  152
 16  ω     70.00 189.00   0.50    1.00    --  101.60  50.00 -60.00  238
 17  ω     64.00 145.00   0.50    1.00    --  101.60 -82.00-120.00  162
 18  ω      3.00  29.00   0.50    0.50    --   42.10 -77.00  60.00   52
 19  ω    105.00 132.00   0.50    0.50    --   42.10  77.00   0.00   54
 20  ω     74.00 124.00   0.50    1.00    --  101.60  50.00-180.00  100
 21  ω    166.00 191.00   0.50    1.00    --  101.60  82.00 120.00   50
 22  ω    143.00 184.00   0.50    1.00    --  101.60  82.00   0.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0249845000
_diffrn_orient_matrix_UB_12      0.1210167000
_diffrn_orient_matrix_UB_13      0.0738408000
_diffrn_orient_matrix_UB_21      0.0883873000
_diffrn_orient_matrix_UB_22      0.0222855000
_diffrn_orient_matrix_UB_23      -0.0409945000
_diffrn_orient_matrix_UB_31      -0.0498668000
_diffrn_orient_matrix_UB_32      0.1005774000
_diffrn_orient_matrix_UB_33      -0.0798346000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3160
_reflns_number_total             3658
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3658
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0634
_refine_ls_restrained_S_all      1.086
_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)+(0.0802P)²+1.2441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1779
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C21(H21A,H21B,H21C)
;
_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
O1 O 0.74787(10) 0.56541(14) 0.65893(10) 0.0349(4) Uani 1 1 d . . . . .
O2 O 0.82173(10) 0.43551(15) 0.78886(11) 0.0409(4) Uani 1 1 d . . . . .
N1 N 0.37793(16) 0.0601(2) 0.49377(16) 0.0551(6) Uani 1 1 d . . . . .
C1 C 0.55820(13) 0.35421(19) 0.64361(14) 0.0293(4) Uani 1 1 d . . . . .
C2 C 0.56470(13) 0.4232(2) 0.73632(14) 0.0335(4) Uani 1 1 d . . . . .
H2 H 0.618207 0.413370 0.785673 0.040 Uiso 1 1 calc R U . . .
C3 C 0.49463(15) 0.5050(2) 0.75714(15) 0.0378(5) Uani 1 1 d . . . . .
H3 H 0.500567 0.550849 0.820271 0.045 Uiso 1 1 calc R U . . .
C4 C 0.41604(14) 0.5205(2) 0.68649(16) 0.0390(5) Uani 1 1 d . . . . .
H4 H 0.368546 0.578455 0.700134 0.047 Uiso 1 1 calc R U . . .
C5 C 0.40727(13) 0.4506(2) 0.59556(15) 0.0358(5) Uani 1 1 d . . . . .
H5 H 0.352904 0.459536 0.547385 0.043 Uiso 1 1 calc R U . . .
C6 C 0.47711(13) 0.3675(2) 0.57392(14) 0.0303(4) Uani 1 1 d . . . . .
C7 C 0.46138(14) 0.2908(2) 0.47338(14) 0.0353(5) Uani 1 1 d . . . . .
H7A H 0.424258 0.348587 0.420988 0.042 Uiso 1 1 calc R U . . .
H7B H 0.520345 0.272915 0.452451 0.042 Uiso 1 1 calc R U . . .
C8 C 0.41503(14) 0.1605(2) 0.48263(14) 0.0358(5) Uani 1 1 d . . . . .
C9 C 0.63422(14) 0.2697(2) 0.62087(14) 0.0325(4) Uani 1 1 d . . . . .
H9 H 0.6172(16) 0.181(3) 0.5847(19) 0.045(6) Uiso 1 1 d . . . . .
C10 C 0.72265(13) 0.3003(2) 0.64552(14) 0.0337(5) Uani 1 1 d . . . . .
C12 C 0.86226(14) 0.5730(2) 0.80473(15) 0.0368(5) Uani 1 1 d . . . . .
C13 C 0.87233(19) 0.6079(3) 0.91602(17) 0.0533(6) Uani 1 1 d . . . . .
H13A H 0.813244 0.599773 0.937015 0.080 Uiso 1 1 calc R U . . .
H13B H 0.894855 0.702553 0.927405 0.080 Uiso 1 1 calc R U . . .
H13C H 0.915395 0.543843 0.955439 0.080 Uiso 1 1 calc R U . . .
C14 C 0.95470(16) 0.5630(3) 0.7744(2) 0.0626(8) Uani 1 1 d . . . . .
H14A H 0.990644 0.491423 0.814731 0.094 Uiso 1 1 calc R U . . .
H14B H 0.985960 0.651885 0.786202 0.094 Uiso 1 1 calc R U . . .
H14C H 0.947252 0.539093 0.702801 0.094 Uiso 1 1 calc R U . . .
C15 C 0.79345(14) 0.6645(2) 0.73336(14) 0.0344(5) Uani 1 1 d . . . . .
C16 C 0.8363(2) 0.7754(3) 0.6775(2) 0.0589(7) Uani 1 1 d . . . . .
H16A H 0.875264 0.731992 0.635392 0.088 Uiso 1 1 calc R U . . .
H16B H 0.872714 0.837187 0.726318 0.088 Uiso 1 1 calc R U . . .
H16C H 0.788487 0.828468 0.634833 0.088 Uiso 1 1 calc R U . . .
C17 C 0.72077(16) 0.7278(3) 0.7840(2) 0.0510(6) Uani 1 1 d . . . . .
H17A H 0.674135 0.770498 0.732973 0.077 Uiso 1 1 calc R U . . .
H17B H 0.748065 0.798044 0.832398 0.077 Uiso 1 1 calc R U . . .
H17C H 0.693089 0.655654 0.819488 0.077 Uiso 1 1 calc R U . . .
C18 C 0.79284(15) 0.2005(2) 0.61834(18) 0.0429(5) Uani 1 1 d . . . . .
H18A H 0.760994 0.123507 0.578593 0.051 Uiso 1 1 calc R U . . .
H18B H 0.828055 0.161268 0.681164 0.051 Uiso 1 1 calc R U . . .
C19 C 0.85885(16) 0.2673(3) 0.55764(18) 0.0480(6) Uani 1 1 d . . . . .
H19A H 0.895183 0.337534 0.600508 0.058 Uiso 1 1 calc R U . . .
H19B H 0.901237 0.195576 0.541942 0.058 Uiso 1 1 calc R U . . .
C20 C 0.8150(2) 0.3346(4) 0.4610(2) 0.0647(8) Uani 1 1 d . . . . .
H20A H 0.771347 0.404972 0.475969 0.078 Uiso 1 1 calc R U . . .
H20B H 0.780435 0.264201 0.416670 0.078 Uiso 1 1 calc R U . . .
C21 C 0.8822(3) 0.4026(4) 0.4056(2) 0.0822(10) Uani 1 1 d . . . . .
H21A H 0.849811 0.444493 0.343288 0.123 Uiso 1 1 calc R U . . .
H21B H 0.924899 0.333217 0.389211 0.123 Uiso 1 1 calc R U . . .
H21C H 0.915658 0.474155 0.448385 0.123 Uiso 1 1 calc R U . . .
B1 B 0.76231(15) 0.4372(2) 0.69953(16) 0.0314(5) 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
O1 C15 1.466(2) . ?
O1 B1 1.360(3) . ?
O2 C12 1.464(3) . ?
O2 B1 1.363(3) . ?
N1 C8 1.144(3) . ?
C1 C2 1.405(3) . ?
C1 C6 1.402(3) . ?
C1 C9 1.479(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C6 C7 1.527(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.458(3) . ?
C9 H9 1.00(3) . ?
C9 C10 1.340(3) . ?
C10 C18 1.521(3) . ?
C10 B1 1.577(3) . ?
C12 C13 1.519(3) . ?
C12 C14 1.516(3) . ?
C12 C15 1.555(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.519(3) . ?
C15 C17 1.515(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.536(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.499(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.509(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
B1 O1 C15 107.61(15) . . ?
B1 O2 C12 107.84(16) . . ?
C2 C1 C9 121.00(17) . . ?
C6 C1 C2 117.74(18) . . ?
C6 C1 C9 121.26(17) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.28(18) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.34(18) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.3(2) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.86(19) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 121.81(18) . . ?
C5 C6 C1 120.41(17) . . ?
C5 C6 C7 117.78(17) . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 C6 110.21(16) . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
N1 C8 C7 177.1(2) . . ?
C1 C9 H9 116.1(14) . . ?
C10 C9 C1 126.17(18) . . ?
C10 C9 H9 117.8(14) . . ?
C9 C10 C18 119.68(18) . . ?
C9 C10 B1 125.05(18) . . ?
C18 C10 B1 115.25(17) . . ?
O2 C12 C13 108.17(18) . . ?
O2 C12 C14 106.12(19) . . ?
O2 C12 C15 102.56(15) . . ?
C13 C12 C15 114.90(19) . . ?
C14 C12 C13 110.3(2) . . ?
C14 C12 C15 113.9(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 C12 102.99(16) . . ?
O1 C15 C16 108.07(17) . . ?
O1 C15 C17 106.83(16) . . ?
C16 C15 C12 114.72(19) . . ?
C17 C15 C12 113.69(18) . . ?
C17 C15 C16 109.9(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 H18A 108.8 . . ?
C10 C18 H18B 108.8 . . ?
C10 C18 C19 113.58(18) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C18 C19 H19A 108.5 . . ?
C18 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C20 C19 C18 115.0(2) . . ?
C20 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
C19 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
C19 C20 C21 113.1(3) . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 B1 O2 113.45(18) . . ?
O1 B1 C10 124.28(17) . . ?
O2 B1 C10 122.02(19) . . ?

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
O2 C12 C15 O1 -23.05(19) . . . . ?
O2 C12 C15 C16 -140.23(19) . . . . ?
O2 C12 C15 C17 92.1(2) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C6 C7 C8 93.6(2) . . . . ?
C1 C9 C10 C18 178.75(18) . . . . ?
C1 C9 C10 B1 -3.1(3) . . . . ?
C2 C1 C6 C5 2.2(3) . . . . ?
C2 C1 C6 C7 -176.78(18) . . . . ?
C2 C1 C9 C10 -39.1(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C4 C5 C6 C7 178.39(19) . . . . ?
C5 C6 C7 C8 -85.5(2) . . . . ?
C6 C1 C2 C3 -2.0(3) . . . . ?
C6 C1 C9 C10 141.3(2) . . . . ?
C9 C1 C2 C3 178.44(18) . . . . ?
C9 C1 C6 C5 -178.20(18) . . . . ?
C9 C1 C6 C7 2.8(3) . . . . ?
C9 C10 C18 C19 125.8(2) . . . . ?
C9 C10 B1 O1 -63.7(3) . . . . ?
C9 C10 B1 O2 122.4(2) . . . . ?
C10 C18 C19 C20 -57.2(3) . . . . ?
C12 O2 B1 O1 -8.7(2) . . . . ?
C12 O2 B1 C10 165.81(18) . . . . ?
C13 C12 C15 O1 -140.16(19) . . . . ?
C13 C12 C15 C16 102.7(2) . . . . ?
C13 C12 C15 C17 -25.0(3) . . . . ?
C14 C12 C15 O1 91.2(2) . . . . ?
C14 C12 C15 C16 -26.0(3) . . . . ?
C14 C12 C15 C17 -153.6(2) . . . . ?
C15 O1 B1 O2 -7.3(2) . . . . ?
C15 O1 B1 C10 178.26(18) . . . . ?
C18 C10 B1 O1 114.6(2) . . . . ?
C18 C10 B1 O2 -59.4(3) . . . . ?
C18 C19 C20 C21 178.2(2) . . . . ?
B1 O1 C15 C12 18.9(2) . . . . ?
B1 O1 C15 C16 140.7(2) . . . . ?
B1 O1 C15 C17 -101.1(2) . . . . ?
B1 O2 C12 C13 141.50(19) . . . . ?
B1 O2 C12 C14 -100.1(2) . . . . ?
B1 O2 C12 C15 19.7(2) . . . . ?
B1 C10 C18 C19 -52.5(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 1.503
_oxdiff_exptl_absorpt_empirical_full_min 0.281
####################################################################### 
# 
# 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_h-385-1
_audit_block_doi                 10.5517/ccdc.csd.cc2hmdsb
_database_code_depnum_ccdc_archive 'CCDC 2312562'
loop_
_audit_author_name
_audit_author_address
'Jiuzhong Huang'
;Gannan Medical University
China
;
_audit_update_record             
;
2023-12-07 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_audit_creation_date             2023-11-30
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 B N O2'
_chemical_formula_sum            'C22 H24 B N O2'
_chemical_formula_weight         345.23
_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 0.0181 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                   10.1597(2)
_cell_length_b                   10.2937(2)
_cell_length_c                   11.2498(3)
_cell_angle_alpha                79.933(2)
_cell_angle_beta                 89.723(2)
_cell_angle_gamma                76.120(2)
_cell_volume                     1123.73(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10955
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.4480
_cell_measurement_theta_min      3.9780
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.501
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.020
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13108
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.549
_diffrn_reflns_theta_min         3.994
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  17.00   0.50    0.20    --  -48.13  87.00 -38.00  174
  2  ω   -105.00 -80.00   0.50    0.40    -- -104.00  87.00 -38.00   50
  3  ω    -41.00 -15.00   0.50    0.20    --  -48.13 125.00  60.00   52
  4  ω    -64.00 -32.00   0.50    0.40    -- -104.00  57.00 150.00   64
  5  ω    -57.00 -32.00   0.50    0.40    -- -104.00  57.00 120.00   50
  6  ω    -86.00 -60.00   0.50    0.40    -- -104.00  77.00  90.00   52
  7  ω    -61.00 -32.00   0.50    0.40    -- -104.00  57.00-120.00   58
  8  ω    -59.00 -32.00   0.50    0.40    -- -104.00  57.00-180.00   54
  9  ω    -37.00  18.00   0.50    0.20    --  -48.13  38.00 -90.00  110
 10  ω    -40.00  12.00   0.50    0.20    --  -48.13  38.00-150.00  104
 11  ω    144.00 173.00   0.50    0.40    --  104.75  38.00  90.00   58
 12  ω     86.00 154.00   0.50    0.40    --  104.75  87.00 -38.00  136
 13  ω     93.00 135.00   0.50    0.40    --  104.75  57.00 -90.00   84
 14  ω    148.00 173.00   0.50    0.40    --  104.75  57.00 -90.00   50
 15  ω     94.00 177.00   0.50    0.40    --  104.75  38.00-120.00  166
 16  ω     21.00  55.00   0.50    0.20    --   48.13-125.00 120.00   68
 17  ω     37.00  63.00   0.50    0.40    --  104.75 -99.00  30.00   52
 18  ω     38.00 111.00   0.50    0.40    --  104.75-125.00   0.00  146
 19  ω     44.00 106.00   0.50    0.40    --  104.75 -99.00  60.00  124
 20  ω     47.00 102.00   0.50    0.40    --  104.75 -99.00 120.00  110
 21  ω     73.00 106.00   0.50    0.40    --  104.75 -99.00 -30.00   66
 22  ω     51.00 100.00   0.50    0.40    --  104.75 -99.00 -60.00   98
 23  ω     67.00  98.00   0.50    0.40    --  104.75 -99.00-120.00   62
 24  ω     36.00 100.00   0.50    0.40    --  104.75-125.00-150.00  128
 25  ω     48.00 108.00   0.50    0.40    --  104.75-107.00-141.20  120
 26  ω     58.00  84.00   0.50    0.40    --  104.75 -87.00-155.00   52
 27  ω      1.00  56.00   0.50    0.20    --   48.13 -87.00-155.00  110
 28  ω     66.00 100.00   0.50    0.40    --  104.75 -99.00  30.00   68
 29  ω     42.00  68.00   0.50    0.40    --  104.75 -77.00  90.00   52
 30  ω     71.00  96.00   0.50    0.40    --  104.75 -77.00  90.00   50
 31  ω     36.00  64.00   0.50    0.40    --  104.75 -57.00   0.00   56
 32  ω     42.00  68.00   0.50    0.40    --  104.75 -57.00 -30.00   52
 33  ω     37.00  66.00   0.50    0.40    --  104.75 -57.00-120.00   58
 34  ω     42.00  67.00   0.50    0.40    --  104.75 -57.00-150.00   50
 35  ω    -23.00  28.00   0.50    0.20    --   48.13 -19.00 -60.00  102
 36  ω    -17.00  45.00   0.50    0.20    --   48.13 -38.00  30.00  124
 37  ω   -168.00-134.00   0.50    0.40    -- -104.00 -19.00 -30.00   68
 38  ω   -171.00 -97.00   0.50    0.40    -- -104.00 -38.00  60.00  148
 39  ω   -124.00 -94.00   0.50    0.40    -- -104.00 -19.00 -30.00   60
 40  ω   -157.00-117.00   0.50    0.40    -- -104.00 -87.00-155.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0757286000
_diffrn_orient_matrix_UB_12      0.1144938000
_diffrn_orient_matrix_UB_13      -0.0154026000
_diffrn_orient_matrix_UB_21      0.0486089000
_diffrn_orient_matrix_UB_22      -0.0341531000
_diffrn_orient_matrix_UB_23      -0.1233381000
_diffrn_orient_matrix_UB_31      -0.1278119000
_diffrn_orient_matrix_UB_32      0.1013722000
_diffrn_orient_matrix_UB_33      -0.0626400000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4316
_reflns_number_total             4524
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4524
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0649
_refine_ls_restrained_S_all      1.065
_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)+(0.0691P)²+0.7494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1641
_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 Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C17(H17), C18(H18), C19(H19),
 C21(H21)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
_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
O1 O 0.86581(18) 0.63224(13) 0.87701(13) 0.0598(5) Uani 1 1 d . . . . .
O2 O 0.75029(14) 0.83457(12) 0.77302(11) 0.0435(3) Uani 1 1 d . . . . .
N1 N 0.8153(2) 0.9993(2) 0.20590(19) 0.0636(6) Uani 1 1 d . . . . .
C1 C 0.60203(19) 1.03288(18) 0.33623(17) 0.0400(4) Uani 1 1 d . . . . .
H1A H 0.519547 1.074813 0.283677 0.048 Uiso 1 1 calc R U . . .
H1B H 0.609704 1.095319 0.392109 0.048 Uiso 1 1 calc R U . . .
C2 C 0.83282(18) 0.45656(18) 0.45433(17) 0.0369(4) Uani 1 1 d . . . . .
H2 H 0.804339 0.551375 0.423795 0.044 Uiso 1 1 calc R U . . .
C3 C 0.8456(2) 0.3649(2) 0.37573(18) 0.0435(4) Uani 1 1 d . . . . .
H3 H 0.825984 0.397348 0.291802 0.052 Uiso 1 1 calc R U . . .
C4 C 0.8868(2) 0.2265(2) 0.4186(2) 0.0465(5) Uani 1 1 d . . . . .
H4 H 0.893803 0.163983 0.364563 0.056 Uiso 1 1 calc R U . . .
C5 C 0.9177(2) 0.1796(2) 0.5401(2) 0.0495(5) Uani 1 1 d . . . . .
H5 H 0.946521 0.084647 0.569861 0.059 Uiso 1 1 calc R U . . .
C6 C 0.90659(19) 0.27126(18) 0.61894(19) 0.0422(4) Uani 1 1 d . . . . .
H6 H 0.930216 0.238222 0.702214 0.051 Uiso 1 1 calc R U . . .
C7 C 0.85212(17) 0.50158(17) 0.66720(16) 0.0339(4) Uani 1 1 d . . . . .
H7 H 0.908102 0.463503 0.738162 0.041 Uiso 1 1 calc R U . . .
C8 C 0.77773(16) 0.62916(16) 0.66507(15) 0.0305(3) Uani 1 1 d . . . . .
C10 C 0.6468(2) 0.9004(3) 0.9492(2) 0.0678(8) Uani 1 1 d . . . . .
H10A H 0.587541 0.980841 0.899793 0.102 Uiso 1 1 calc R U . . .
H10B H 0.661876 0.919764 1.029634 0.102 Uiso 1 1 calc R U . . .
H10C H 0.603716 0.823866 0.956854 0.102 Uiso 1 1 calc R U . . .
C11 C 0.78153(17) 0.86435(17) 0.88961(15) 0.0332(4) Uani 1 1 d . . . . .
C12 C 0.8434(3) 0.9842(2) 0.8719(3) 0.0705(8) Uani 1 1 d . . . . .
H12A H 0.919868 0.968603 0.818408 0.106 Uiso 1 1 calc R U . . .
H12B H 0.875630 0.996458 0.950151 0.106 Uiso 1 1 calc R U . . .
H12C H 0.775155 1.066064 0.835373 0.106 Uiso 1 1 calc R U . . .
C13 C 0.87882(17) 0.72764(16) 0.95431(15) 0.0331(4) Uani 1 1 d . . . . .
C14 C 0.8409(3) 0.6738(2) 1.0795(2) 0.0666(7) Uani 1 1 d . . . . .
H14A H 0.750314 0.656651 1.076162 0.100 Uiso 1 1 calc R U . . .
H14B H 0.840784 0.740821 1.131603 0.100 Uiso 1 1 calc R U . . .
H14C H 0.906986 0.588759 1.112381 0.100 Uiso 1 1 calc R U . . .
C15 C 1.0264(2) 0.7302(2) 0.9564(3) 0.0728(8) Uani 1 1 d . . . . .
H15A H 1.082212 0.637663 0.982782 0.109 Uiso 1 1 calc R U . . .
H15B H 1.041879 0.788304 1.012631 0.109 Uiso 1 1 calc R U . . .
H15C H 1.051241 0.766321 0.875203 0.109 Uiso 1 1 calc R U . . .
C16 C 0.67463(15) 0.70366(15) 0.56725(14) 0.0281(3) Uani 1 1 d . . . . .
C17 C 0.56295(17) 0.65323(16) 0.54433(16) 0.0326(4) Uani 1 1 d . . . . .
H17 H 0.553634 0.569497 0.590353 0.039 Uiso 1 1 calc R U . . .
C18 C 0.46584(17) 0.72394(18) 0.45536(17) 0.0373(4) Uani 1 1 d . . . . .
H18 H 0.390340 0.688666 0.440840 0.045 Uiso 1 1 calc R U . . .
C19 C 0.47839(17) 0.84607(18) 0.38735(16) 0.0370(4) Uani 1 1 d . . . . .
H19 H 0.411775 0.894118 0.326079 0.044 Uiso 1 1 calc R U . . .
C20 C 0.58828(16) 0.89817(16) 0.40875(15) 0.0319(4) Uani 1 1 d . . . . .
C21 C 0.68510(16) 0.82746(16) 0.49928(15) 0.0299(3) Uani 1 1 d . . . . .
H21 H 0.759287 0.864135 0.514902 0.036 Uiso 1 1 calc R U . . .
C22 C 0.7206(2) 1.01509(18) 0.26196(16) 0.0398(4) Uani 1 1 d . . . . .
C23 C 0.86136(16) 0.41091(17) 0.57790(16) 0.0328(4) Uani 1 1 d . . . . .
B1 B 0.79919(19) 0.70039(18) 0.77246(17) 0.0305(4) 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
O1 C13 1.449(2) . ?
O1 B1 1.351(2) . ?
O2 C11 1.451(2) . ?
O2 B1 1.352(2) . ?
N1 C22 1.142(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C20 1.518(2) . ?
C1 C22 1.456(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(3) . ?
C2 C23 1.396(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(3) . ?
C6 H6 0.9500 . ?
C6 C23 1.394(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.345(2) . ?
C7 C23 1.474(2) . ?
C8 C16 1.492(2) . ?
C8 B1 1.560(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 C11 1.516(3) . ?
C11 C12 1.497(3) . ?
C11 C13 1.571(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.505(3) . ?
C13 C15 1.507(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.398(2) . ?
C16 C21 1.394(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(2) . ?
C20 C21 1.393(2) . ?
C21 H21 0.9500 . ?

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
B1 O1 C13 109.68(13) . . ?
B1 O2 C11 109.54(13) . . ?
H1A C1 H1B 108.0 . . ?
C20 C1 H1A 109.3 . . ?
C20 C1 H1B 109.3 . . ?
C22 C1 H1A 109.3 . . ?
C22 C1 H1B 109.3 . . ?
C22 C1 C20 111.46(15) . . ?
C3 C2 H2 119.7 . . ?
C3 C2 C23 120.63(17) . . ?
C23 C2 H2 119.7 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.48(19) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.69(18) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.99(18) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C23 121.10(18) . . ?
C23 C6 H6 119.5 . . ?
C8 C7 H7 114.6 . . ?
C8 C7 C23 130.84(15) . . ?
C23 C7 H7 114.6 . . ?
C7 C8 C16 123.38(15) . . ?
C7 C8 B1 117.68(14) . . ?
C16 C8 B1 118.93(14) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
O2 C11 C10 105.82(16) . . ?
O2 C11 C12 109.68(18) . . ?
O2 C11 C13 103.34(12) . . ?
C10 C11 C13 113.68(16) . . ?
C12 C11 C10 109.3(2) . . ?
C12 C11 C13 114.43(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 C11 103.06(12) . . ?
O1 C13 C14 108.12(17) . . ?
O1 C13 C15 106.31(18) . . ?
C14 C13 C11 115.34(16) . . ?
C14 C13 C15 109.2(2) . . ?
C15 C13 C11 114.06(16) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C8 120.80(14) . . ?
C21 C16 C8 120.71(14) . . ?
C21 C16 C17 118.46(14) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.73(16) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.22(15) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.02(15) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C1 120.52(15) . . ?
C19 C20 C21 119.62(15) . . ?
C21 C20 C1 119.84(15) . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 120.93(15) . . ?
C20 C21 H21 119.5 . . ?
N1 C22 C1 178.5(2) . . ?
C2 C23 C7 124.02(15) . . ?
C6 C23 C2 118.06(16) . . ?
C6 C23 C7 117.87(16) . . ?
O1 B1 O2 112.86(15) . . ?
O1 B1 C8 122.89(15) . . ?
O2 B1 C8 124.22(15) . . ?

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
O2 C11 C13 O1 -11.75(18) . . . . ?
O2 C11 C13 C14 -129.34(19) . . . . ?
O2 C11 C13 C15 103.0(2) . . . . ?
C1 C20 C21 C16 179.90(15) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C2 C23 C6 1.8(3) . . . . ?
C3 C2 C23 C7 179.13(17) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C23 1.6(3) . . . . ?
C5 C6 C23 C2 -2.6(3) . . . . ?
C5 C6 C23 C7 179.89(18) . . . . ?
C7 C8 C16 C17 60.4(2) . . . . ?
C7 C8 C16 C21 -121.78(19) . . . . ?
C7 C8 B1 O1 -14.2(3) . . . . ?
C7 C8 B1 O2 168.02(18) . . . . ?
C8 C7 C23 C2 25.3(3) . . . . ?
C8 C7 C23 C6 -157.31(19) . . . . ?
C8 C16 C17 C18 178.57(16) . . . . ?
C8 C16 C21 C20 -179.27(15) . . . . ?
C10 C11 C13 O1 102.5(2) . . . . ?
C10 C11 C13 C14 -15.1(3) . . . . ?
C10 C11 C13 C15 -142.7(2) . . . . ?
C11 O2 B1 O1 -1.7(2) . . . . ?
C11 O2 B1 C8 176.32(16) . . . . ?
C12 C11 C13 O1 -130.9(2) . . . . ?
C12 C11 C13 C14 111.5(2) . . . . ?
C12 C11 C13 C15 -16.1(3) . . . . ?
C13 O1 B1 O2 -6.8(2) . . . . ?
C13 O1 B1 C8 175.18(16) . . . . ?
C16 C8 B1 O1 164.51(18) . . . . ?
C16 C8 B1 O2 -13.3(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C16 C21 C20 -1.4(2) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C18 C19 C20 C1 -179.04(16) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C16 1.2(3) . . . . ?
C21 C16 C17 C18 0.7(2) . . . . ?
C22 C1 C20 C19 -115.07(19) . . . . ?
C22 C1 C20 C21 66.3(2) . . . . ?
C23 C2 C3 C4 0.1(3) . . . . ?
C23 C7 C8 C16 5.3(3) . . . . ?
C23 C7 C8 B1 -176.10(17) . . . . ?
B1 O1 C13 C11 11.4(2) . . . . ?
B1 O1 C13 C14 133.96(19) . . . . ?
B1 O1 C13 C15 -108.9(2) . . . . ?
B1 O2 C11 C10 -111.23(18) . . . . ?
B1 O2 C11 C12 130.95(18) . . . . ?
B1 O2 C11 C13 8.52(19) . . . . ?
B1 C8 C16 C17 -118.22(17) . . . . ?
B1 C8 C16 C21 59.6(2) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 0.500 0.000 228.5 49.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.273
_oxdiff_exptl_absorpt_empirical_full_min 0.749
####################################################################### 
# 
# 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_385-8_2
_audit_block_doi                 10.5517/ccdc.csd.cc2hmdtc
_database_code_depnum_ccdc_archive 'CCDC 2312563'
loop_
_audit_author_name
_audit_author_address
'Jiuzhong Huang'
;Gannan Medical University
China
;
_audit_update_record             
;
2023-12-07 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_audit_creation_date             2023-12-06
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 B N O2'
_chemical_formula_sum            'C22 H24 B N O2'
_chemical_formula_weight         345.23
_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      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                   9.6547(10)
_cell_length_b                   10.2621(13)
_cell_length_c                   10.6861(15)
_cell_angle_alpha                102.169(11)
_cell_angle_beta                 105.217(10)
_cell_angle_gamma                103.684(10)
_cell_volume                     949.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3179
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.7220
_cell_measurement_theta_min      2.2730
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7165
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.064
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  71.00   1.00    1.50    --   11.90  57.00 -30.00   87
  2  ω     48.00  78.00   1.00    1.50    --   11.90 178.00 -60.00   30
  3  ω    -36.00  61.00   1.00    1.50    --  -11.27  57.00-180.00   97
  4  ω    -77.00  13.00   1.00    1.50    --  -11.27 -57.00  30.00   90
  5  ω    -82.00 -57.00   1.00    1.50    --  -11.27 -38.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0032808000
_diffrn_orient_matrix_UB_12      -0.0026766000
_diffrn_orient_matrix_UB_13      -0.0659968000
_diffrn_orient_matrix_UB_21      0.0758989000
_diffrn_orient_matrix_UB_22      0.0442712000
_diffrn_orient_matrix_UB_23      0.0284629000
_diffrn_orient_matrix_UB_31      0.0252838000
_diffrn_orient_matrix_UB_32      -0.0596813000
_diffrn_orient_matrix_UB_33      -0.0020003000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2706
_reflns_number_total             3351
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3351
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.076
_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)+(0.0472P)²+0.3589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1232
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C)
;
_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
O1 O 0.85648(16) 0.56777(12) 0.57958(13) 0.0319(3) Uani 1 1 d . . . . .
O2 O 0.76813(16) 0.74250(12) 0.66270(12) 0.0320(3) Uani 1 1 d . . . . .
N1 N 0.3967(2) -0.12060(19) 0.5811(2) 0.0517(5) Uani 1 1 d . . . . .
C1 C 0.7605(2) 0.33722(17) 0.86583(18) 0.0234(4) Uani 1 1 d . . . . .
C2 C 0.8075(2) 0.38735(18) 1.00683(18) 0.0275(4) Uani 1 1 d . . . . .
H2 H 0.854799 0.484771 1.050918 0.033 Uiso 1 1 calc R U . . .
C3 C 0.7852(2) 0.29519(19) 1.08233(18) 0.0308(5) Uani 1 1 d . . . . .
H3 H 0.817961 0.329931 1.178371 0.037 Uiso 1 1 calc R U . . .
C4 C 0.7161(2) 0.15343(19) 1.02027(18) 0.0292(4) Uani 1 1 d . . . . .
H4 H 0.699346 0.091755 1.073539 0.035 Uiso 1 1 calc R U . . .
C5 C 0.6710(2) 0.10075(17) 0.88062(18) 0.0253(4) Uani 1 1 d . . . . .
C6 C 0.6946(2) 0.19309(18) 0.80495(18) 0.0248(4) Uani 1 1 d . . . . .
H6 H 0.665124 0.157331 0.709175 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6034(2) -0.05594(19) 0.81495(19) 0.0331(5) Uani 1 1 d . . . . .
H7A H 0.684617 -0.095531 0.802407 0.040 Uiso 1 1 calc R U . . .
H7B H 0.560311 -0.098996 0.876483 0.040 Uiso 1 1 calc R U . . .
C8 C 0.4862(2) -0.09282(19) 0.6845(2) 0.0345(5) Uani 1 1 d . . . . .
C9 C 0.7804(2) 0.42749(17) 0.77751(17) 0.0244(4) Uani 1 1 d . . . . .
H9 H 0.789485 0.382617 0.694013 0.029 Uiso 1 1 calc R U . . .
C10 C 0.78801(19) 0.56278(17) 0.79547(17) 0.0231(4) Uani 1 1 d . . . . .
C11 C 0.7687(2) 0.65467(17) 0.91399(17) 0.0234(4) Uani 1 1 d . . . . .
C12 C 0.8835(2) 0.77743(19) 0.99368(19) 0.0303(4) Uani 1 1 d . . . . .
H12 H 0.975474 0.800327 0.974501 0.036 Uiso 1 1 calc R U . . .
C13 C 0.8654(3) 0.8665(2) 1.1004(2) 0.0372(5) Uani 1 1 d . . . . .
H13 H 0.945269 0.949468 1.154632 0.045 Uiso 1 1 calc R U . . .
C14 C 0.7324(3) 0.8358(2) 1.12873(19) 0.0359(5) Uani 1 1 d . . . . .
H14 H 0.720617 0.896990 1.202564 0.043 Uiso 1 1 calc R U . . .
C15 C 0.6165(2) 0.7158(2) 1.0495(2) 0.0336(5) Uani 1 1 d . . . . .
H15 H 0.523970 0.694781 1.067911 0.040 Uiso 1 1 calc R U . . .
C16 C 0.6347(2) 0.62588(18) 0.94310(19) 0.0281(4) Uani 1 1 d . . . . .
H16 H 0.554316 0.543166 0.889164 0.034 Uiso 1 1 calc R U . . .
C17 C 1.0428(2) 0.7597(2) 0.5639(2) 0.0400(5) Uani 1 1 d . . . . .
H17A H 1.061673 0.813321 0.657480 0.060 Uiso 1 1 calc R U . . .
H17B H 1.064043 0.824408 0.510860 0.060 Uiso 1 1 calc R U . . .
H17C H 1.108415 0.700035 0.563320 0.060 Uiso 1 1 calc R U . . .
C18 C 0.8783(2) 0.66843(19) 0.50197(19) 0.0322(5) Uani 1 1 d . . . . .
C19 C 0.8446(3) 0.5885(2) 0.35623(19) 0.0395(5) Uani 1 1 d . . . . .
H19A H 0.920746 0.541311 0.349895 0.059 Uiso 1 1 calc R U . . .
H19B H 0.846575 0.653638 0.301124 0.059 Uiso 1 1 calc R U . . .
H19C H 0.744429 0.518465 0.322950 0.059 Uiso 1 1 calc R U . . .
C20 C 0.8133(3) 0.90033(19) 0.5286(2) 0.0355(5) Uani 1 1 d . . . . .
H20A H 0.735469 0.941971 0.543984 0.053 Uiso 1 1 calc R U . . .
H20B H 0.825225 0.906413 0.441565 0.053 Uiso 1 1 calc R U . . .
H20C H 0.909236 0.951189 0.601707 0.053 Uiso 1 1 calc R U . . .
C21 C 0.7669(2) 0.74898(19) 0.52654(18) 0.0310(5) Uani 1 1 d . . . . .
C22 C 0.6056(2) 0.6723(2) 0.4308(2) 0.0406(5) Uani 1 1 d . . . . .
H22A H 0.579953 0.572877 0.426585 0.061 Uiso 1 1 calc R U . . .
H22B H 0.597709 0.681703 0.339997 0.061 Uiso 1 1 calc R U . . .
H22C H 0.535580 0.713307 0.464398 0.061 Uiso 1 1 calc R U . . .
B1 B 0.8058(2) 0.6255(2) 0.6780(2) 0.0236(5) 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
O1 C18 1.466(2) . ?
O1 B1 1.357(2) . ?
O2 C21 1.468(2) . ?
O2 B1 1.364(2) . ?
N1 C8 1.139(3) . ?
C1 C2 1.395(2) . ?
C1 C6 1.396(2) . ?
C1 C9 1.472(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
C5 C6 1.386(2) . ?
C5 C7 1.514(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.454(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.342(2) . ?
C10 C11 1.494(2) . ?
C10 B1 1.555(3) . ?
C11 C12 1.390(3) . ?
C11 C16 1.388(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.375(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 C18 1.523(3) . ?
C18 C19 1.508(3) . ?
C18 C21 1.545(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C21 1.505(3) . ?
C21 C22 1.529(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
B1 O1 C18 106.49(14) . . ?
B1 O2 C21 106.34(14) . . ?
C2 C1 C6 118.35(16) . . ?
C2 C1 C9 123.63(16) . . ?
C6 C1 C9 117.99(16) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.93(17) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.95(17) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.22(17) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 118.82(16) . . ?
C4 C5 C7 119.44(16) . . ?
C6 C5 C7 121.69(16) . . ?
C1 C6 H6 119.2 . . ?
C5 C6 C1 121.70(16) . . ?
C5 C6 H6 119.2 . . ?
C5 C7 H7A 109.0 . . ?
C5 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C5 113.01(15) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
N1 C8 C7 178.5(2) . . ?
C1 C9 H9 114.7 . . ?
C10 C9 C1 130.65(17) . . ?
C10 C9 H9 114.7 . . ?
C9 C10 C11 125.33(16) . . ?
C9 C10 B1 117.19(16) . . ?
C11 C10 B1 117.29(14) . . ?
C12 C11 C10 119.90(17) . . ?
C16 C11 C10 121.86(16) . . ?
C16 C11 C12 118.12(17) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.43(19) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.66(18) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 121.00(18) . . ?
C15 C16 H16 119.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
O1 C18 C17 106.85(15) . . ?
O1 C18 C19 108.65(15) . . ?
O1 C18 C21 101.96(15) . . ?
C17 C18 C21 113.06(16) . . ?
C19 C18 C17 110.64(18) . . ?
C19 C18 C21 114.93(16) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
O2 C21 C18 101.59(14) . . ?
O2 C21 C20 108.74(14) . . ?
O2 C21 C22 106.89(16) . . ?
C20 C21 C18 115.53(18) . . ?
C20 C21 C22 110.82(17) . . ?
C22 C21 C18 112.45(16) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 B1 O2 113.56(16) . . ?
O1 B1 C10 123.58(16) . . ?
O2 B1 C10 122.84(17) . . ?

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
O1 C18 C21 O2 30.94(17) . . . . ?
O1 C18 C21 C20 148.43(15) . . . . ?
O1 C18 C21 C22 -82.99(18) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C9 C10 C11 -3.5(3) . . . . ?
C1 C9 C10 B1 -178.40(17) . . . . ?
C2 C1 C6 C5 2.1(3) . . . . ?
C2 C1 C9 C10 -28.4(3) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C3 C4 C5 C7 176.54(18) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C4 C5 C7 C8 145.31(19) . . . . ?
C6 C1 C2 C3 -1.5(3) . . . . ?
C6 C1 C9 C10 153.46(19) . . . . ?
C6 C5 C7 C8 -37.3(3) . . . . ?
C7 C5 C6 C1 -178.31(17) . . . . ?
C9 C1 C2 C3 -179.59(17) . . . . ?
C9 C1 C6 C5 -179.69(16) . . . . ?
C9 C10 C11 C12 121.9(2) . . . . ?
C9 C10 C11 C16 -62.1(2) . . . . ?
C9 C10 B1 O1 -19.6(3) . . . . ?
C9 C10 B1 O2 158.77(18) . . . . ?
C10 C11 C12 C13 177.44(16) . . . . ?
C10 C11 C16 C15 -176.89(16) . . . . ?
C11 C10 B1 O1 165.05(17) . . . . ?
C11 C10 B1 O2 -16.6(3) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C11 C16 C15 -0.8(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C16 C11 C12 C13 1.3(3) . . . . ?
C17 C18 C21 O2 -83.40(18) . . . . ?
C17 C18 C21 C20 34.1(2) . . . . ?
C17 C18 C21 C22 162.67(17) . . . . ?
C18 O1 B1 O2 9.9(2) . . . . ?
C18 O1 B1 C10 -171.60(16) . . . . ?
C19 C18 C21 O2 148.26(16) . . . . ?
C19 C18 C21 C20 -94.3(2) . . . . ?
C19 C18 C21 C22 34.3(2) . . . . ?
C21 O2 B1 O1 11.4(2) . . . . ?
C21 O2 B1 C10 -167.12(16) . . . . ?
B1 O1 C18 C17 93.44(18) . . . . ?
B1 O1 C18 C19 -147.17(17) . . . . ?
B1 O1 C18 C21 -25.41(18) . . . . ?
B1 O2 C21 C18 -26.19(18) . . . . ?
B1 O2 C21 C20 -148.48(17) . . . . ?
B1 O2 C21 C22 91.83(17) . . . . ?
B1 C10 C11 C12 -63.2(2) . . . . ?
B1 C10 C11 C16 112.80(18) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.623
_oxdiff_exptl_absorpt_empirical_full_min 0.603
