 
data_1
 
_audit_creation_method            'SHELXL-2019/3'
_shelx_SHELXL_version_number      '2019/3'
_chemical_formula_moiety          'C23 H21 B3 N2 O3'
_chemical_formula_sum	   'C23 H21 B3 N2 O3' 
_chemical_formula_weight          405.85

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'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            61
_space_group_name_H-M_alt         'P b c a'
_space_group_name_Hall            '-P 2ac 2ab'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z-1/2'
 '-x-1/2, y-1/2, z'
 
_cell_length_a                    6.81856(4)
_cell_length_b                    18.79523(11)
_cell_length_c                    32.85532(19)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      4210.62(4)
_cell_formula_units_Z             8
_cell_measurement_temperature     150.0(1) 
_cell_measurement_reflns_used     63787
_cell_measurement_theta_min       4.6840
_cell_measurement_theta_max       77.8260
 
_exptl_crystal_description        'prism'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_diffrn     1.280          
_exptl_crystal_F_000              1696
_exptl_crystal_size_max           0.23
_exptl_crystal_size_mid           0.12
_exptl_crystal_size_min           0.04
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
   0  -12   -2 0.0619
   0   12    2 0.0534
  -4    0   12 0.0988
   4    0  -12 0.0846
   0    0  -21 0.0137
   0    0   21 0.0261
  -4    1   -8 0.1054
   3   -1   14 0.0882
   0   -5  -20 0.0298
  -4   -4   -7 0.1118
   0   -9   14 0.0565

_exptl_absorpt_coefficient_mu     0.657
_exptl_absorpt_correction_T_min   0.883
_exptl_absorpt_correction_T_max   0.975
_exptl_absorpt_correction_type    analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature 	   150.0(1) 
_diffrn_ambient_environment 	   N~2~
_diffrn_source 	             'micro-focus sealed X-ray tube'
_diffrn_source_type 	             'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            'Cu K\a'
_diffrn_radiation_wavelength      1.54184
_diffrn_radiation_monochromator   mirror
_diffrn_measurement_device        'four-circle diffractometer'
_diffrn_measurement_device_type   'SuperNova, Dual, Cu at home/near, HyPix-Arc 100'
_diffrn_detector 		   'Hybrid Pixel Array Detector'
_diffrn_detector_type  	   'HyPix-Arc 100'
_diffrn_reflns_number             94888
_diffrn_reflns_av_unetI/netI      0.0114
_diffrn_reflns_av_R_equivalents   0.0349
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -22
_diffrn_reflns_limit_k_max        22
_diffrn_reflns_limit_l_min        -39
_diffrn_reflns_limit_l_max        39
_diffrn_reflns_theta_min          4.705
_diffrn_reflns_theta_max          66.590
_diffrn_reflns_theta_full         66.590
_diffrn_measured_fraction_theta_max   1.000
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    1.000
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   1.000
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              3713
_reflns_number_gt                 3408
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_cell_refinement        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction         'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_structure_solution     'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement   'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0443P)²+0.9773P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3713
_refine_ls_number_parameters      286
_refine_ls_number_restraints      5
_refine_ls_R_factor_all           0.0333
_refine_ls_R_factor_gt            0.0306
_refine_ls_wR_factor_ref          0.0824
_refine_ls_wR_factor_gt           0.0804
_refine_ls_goodness_of_fit_ref    1.036
_refine_ls_restrained_S_all       1.036
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
N1 N 0.18065(12) 0.55656(5) 0.58979(3) 0.0288(2) Uani 1 1 d . . . . .
C1 C 0.00691(15) 0.56541(6) 0.57023(3) 0.0320(2) Uani 1 1 d D . . . .
B1 B 0.33439(17) 0.62196(6) 0.59517(4) 0.0292(3) Uani 1 1 d . . . . .
O2 O 0.47495(11) 0.69897(4) 0.66311(2) 0.03549(19) Uani 1 1 d . . . . .
N2 N -0.04751(15) 0.63109(5) 0.55906(3) 0.0407(2) Uani 1 1 d D . . . .
H2N H -0.165(2) 0.6372(8) 0.5482(4) 0.061 Uiso 1 1 d D U . . .
H1N H 0.011(2) 0.6680(7) 0.5714(5) 0.061 Uiso 1 1 d D U . . .
C2 C -0.10934(17) 0.50568(6) 0.56073(4) 0.0392(3) Uani 1 1 d . . . . .
H2 H -0.228489 0.511608 0.546136 0.047 Uiso 1 1 calc R U . . .
B2 B 0.56600(18) 0.63633(6) 0.65148(4) 0.0298(3) Uani 1 1 d . . . . .
O3 O 0.22687(11) 0.68159(4) 0.61337(2) 0.03180(18) Uani 1 1 d . . . . .
C3 C -0.05112(18) 0.43951(6) 0.57245(4) 0.0412(3) Uani 1 1 d . . . . .
H3 H -0.128314 0.399118 0.565699 0.049 Uiso 1 1 calc R U . . .
B3 B 0.29793(18) 0.71784(6) 0.64560(4) 0.0314(3) Uani 1 1 d . . . . .
C4 C 0.12258(18) 0.43129(6) 0.59443(4) 0.0380(3) Uani 1 1 d . . . . .
H4 H 0.162825 0.385756 0.603794 0.046 Uiso 1 1 calc R U . . .
C5 C 0.23284(16) 0.49010(6) 0.60212(3) 0.0320(2) Uani 1 1 d . . . . .
H5 H 0.351908 0.484498 0.616786 0.038 Uiso 1 1 calc R U . . .
C6 C 0.41920(14) 0.64331(5) 0.55059(3) 0.0278(2) Uani 1 1 d . . . . .
C7 C 0.42354(16) 0.59798(6) 0.51703(3) 0.0324(2) Uani 1 1 d . . . . .
H7 H 0.366094 0.552087 0.519234 0.039 Uiso 1 1 calc R U . . .
C8 C 0.50959(16) 0.61804(6) 0.48043(4) 0.0366(3) Uani 1 1 d . . . . .
H8 H 0.509723 0.586035 0.458046 0.044 Uiso 1 1 calc R U . . .
C9 C 0.59493(16) 0.68439(6) 0.47648(3) 0.0363(3) Uani 1 1 d . . . . .
H9 H 0.653813 0.698106 0.451479 0.044 Uiso 1 1 calc R U . . .
C10 C 0.59394(15) 0.73067(6) 0.50924(3) 0.0336(2) Uani 1 1 d . . . . .
H10 H 0.652406 0.776359 0.506846 0.040 Uiso 1 1 calc R U . . .
C11 C 0.50735(15) 0.71014(6) 0.54555(3) 0.0306(2) Uani 1 1 d . . . . .
H11 H 0.507733 0.742444 0.567792 0.037 Uiso 1 1 calc R U . . .
C12 C 0.75684(15) 0.61312(6) 0.67428(3) 0.0297(2) Uani 1 1 d . . . . .
C13 C 0.83417(16) 0.54495(6) 0.66959(3) 0.0341(2) Uani 1 1 d . . . . .
H13 H 0.772045 0.512609 0.651496 0.041 Uiso 1 1 calc R U . . .
C14 C 0.99993(17) 0.52325(7) 0.69077(4) 0.0395(3) Uani 1 1 d . . . . .
H14 H 1.048491 0.476200 0.687592 0.047 Uiso 1 1 calc R U . . .
C15 C 1.09422(18) 0.57049(7) 0.71657(4) 0.0415(3) Uani 1 1 d . . . . .
H15 H 1.207805 0.555967 0.731106 0.050 Uiso 1 1 calc R U . . .
C16 C 1.02242(17) 0.63888(7) 0.72108(4) 0.0402(3) Uani 1 1 d . . . . .
H16 H 1.088009 0.671593 0.738415 0.048 Uiso 1 1 calc R U . . .
C17 C 0.85491(16) 0.65977(6) 0.70035(3) 0.0336(2) Uani 1 1 d . . . . .
H17 H 0.805989 0.706674 0.703945 0.040 Uiso 1 1 calc R U . . .
C18 C 0.18574(16) 0.78379(6) 0.66299(3) 0.0330(2) Uani 1 1 d . . . . .
C19 C 0.25433(19) 0.81983(6) 0.69727(4) 0.0398(3) Uani 1 1 d . . . . .
H19 H 0.372298 0.804561 0.709936 0.048 Uiso 1 1 calc R U . . .
C20 C 0.1535(2) 0.87750(7) 0.71320(4) 0.0459(3) Uani 1 1 d . . . . .
H20 H 0.201810 0.900987 0.736760 0.055 Uiso 1 1 calc R U . . .
C21 C -0.0166(2) 0.90084(7) 0.69492(4) 0.0464(3) Uani 1 1 d . . . . .
H21 H -0.084280 0.940941 0.705533 0.056 Uiso 1 1 calc R U . . .
C22 C -0.0887(2) 0.86570(7) 0.66104(4) 0.0448(3) Uani 1 1 d . . . . .
H22 H -0.206689 0.881350 0.648543 0.054 Uiso 1 1 calc R U . . .
C23 C 0.01142(17) 0.80768(6) 0.64539(4) 0.0374(3) Uani 1 1 d . . . . .
H23 H -0.039546 0.783691 0.622241 0.045 Uiso 1 1 calc R U . . .
O1 O 0.49225(10) 0.59627(4) 0.62099(2) 0.03098(18) 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
N1 C1 1.3579(14) . ?
N1 C5 1.3605(13) . ?
N1 B1 1.6251(15) . ?
C1 N2 1.3401(15) . ?
C1 C2 1.4093(16) . ?
B1 O1 1.4531(13) . ?
B1 O3 1.4667(14) . ?
B1 C6 1.6251(15) . ?
O2 B3 1.3833(15) . ?
O2 B2 1.3848(14) . ?
C2 C3 1.3611(17) . ?
B2 O1 1.3504(14) . ?
B2 C12 1.5635(16) . ?
O3 B3 1.3492(15) . ?
C3 C4 1.3958(17) . ?
B3 C18 1.5646(16) . ?
C4 C5 1.3604(16) . ?
C6 C7 1.3938(15) . ?
C6 C11 1.4023(15) . ?
C7 C8 1.3903(16) . ?
C8 C9 1.3822(17) . ?
C9 C10 1.3840(16) . ?
C10 C11 1.3860(15) . ?
C12 C13 1.3940(16) . ?
C12 C17 1.3962(15) . ?
C13 C14 1.3886(16) . ?
C14 C15 1.3857(18) . ?
C15 C16 1.3834(18) . ?
C16 C17 1.3866(16) . ?
C18 C19 1.3952(16) . ?
C18 C23 1.3959(16) . ?
C19 C20 1.3861(17) . ?
C20 C21 1.378(2) . ?
C21 C22 1.3843(19) . ?
C22 C23 1.3856(17) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C1 N1 C5 118.79(9) . . ?
C1 N1 B1 121.44(8) . . ?
C5 N1 B1 119.56(9) . . ?
N2 C1 N1 118.95(10) . . ?
N2 C1 C2 121.16(10) . . ?
N1 C1 C2 119.86(10) . . ?
O1 B1 O3 112.72(9) . . ?
O1 B1 C6 110.16(9) . . ?
O3 B1 C6 110.89(8) . . ?
O1 B1 N1 106.86(8) . . ?
O3 B1 N1 107.45(8) . . ?
C6 B1 N1 108.56(8) . . ?
B3 O2 B2 119.63(9) . . ?
C3 C2 C1 120.09(11) . . ?
O1 B2 O2 120.79(10) . . ?
O1 B2 C12 120.64(10) . . ?
O2 B2 C12 118.57(10) . . ?
B3 O3 B1 121.76(9) . . ?
C2 C3 C4 119.66(11) . . ?
O3 B3 O2 120.68(10) . . ?
O3 B3 C18 120.73(10) . . ?
O2 B3 C18 118.55(10) . . ?
C5 C4 C3 118.37(10) . . ?
C4 C5 N1 123.10(10) . . ?
C7 C6 C11 116.43(10) . . ?
C7 C6 B1 124.72(9) . . ?
C11 C6 B1 118.69(9) . . ?
C8 C7 C6 121.83(10) . . ?
C9 C8 C7 120.23(11) . . ?
C8 C9 C10 119.48(10) . . ?
C9 C10 C11 119.77(10) . . ?
C10 C11 C6 122.25(10) . . ?
C13 C12 C17 117.63(10) . . ?
C13 C12 B2 121.22(10) . . ?
C17 C12 B2 121.15(10) . . ?
C14 C13 C12 121.50(11) . . ?
C15 C14 C13 119.73(11) . . ?
C16 C15 C14 119.78(11) . . ?
C15 C16 C17 120.13(11) . . ?
C16 C17 C12 121.20(11) . . ?
C19 C18 C23 117.62(10) . . ?
C19 C18 B3 121.03(10) . . ?
C23 C18 B3 121.33(10) . . ?
C20 C19 C18 121.22(12) . . ?
C21 C20 C19 120.12(12) . . ?
C20 C21 C22 119.83(11) . . ?
C21 C22 C23 119.94(12) . . ?
C22 C23 C18 121.26(12) . . ?
B2 O1 B1 121.57(9) . . ?
 
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
C5 N1 C1 N2 178.15(10) . . . . ?
B1 N1 C1 N2 -7.25(15) . . . . ?
C5 N1 C1 C2 -4.13(15) . . . . ?
B1 N1 C1 C2 170.48(10) . . . . ?
C1 N1 B1 O1 173.92(9) . . . . ?
C5 N1 B1 O1 -11.51(12) . . . . ?
C1 N1 B1 O3 52.70(12) . . . . ?
C5 N1 B1 O3 -132.73(9) . . . . ?
C1 N1 B1 C6 -67.29(12) . . . . ?
C5 N1 B1 C6 107.28(10) . . . . ?
N2 C1 C2 C3 -179.92(12) . . . . ?
N1 C1 C2 C3 2.40(18) . . . . ?
B3 O2 B2 O1 5.29(15) . . . . ?
B3 O2 B2 C12 -175.01(9) . . . . ?
O1 B1 O3 B3 14.38(14) . . . . ?
C6 B1 O3 B3 -109.65(10) . . . . ?
N1 B1 O3 B3 131.85(9) . . . . ?
C1 C2 C3 C4 0.98(19) . . . . ?
B1 O3 B3 O2 -1.06(15) . . . . ?
B1 O3 B3 C18 176.72(9) . . . . ?
B2 O2 B3 O3 -9.54(15) . . . . ?
B2 O2 B3 C18 172.63(9) . . . . ?
C2 C3 C4 C5 -2.53(18) . . . . ?
C3 C4 C5 N1 0.76(17) . . . . ?
C1 N1 C5 C4 2.59(16) . . . . ?
B1 N1 C5 C4 -172.12(10) . . . . ?
O1 B1 C6 C7 93.46(12) . . . . ?
O3 B1 C6 C7 -141.05(10) . . . . ?
N1 B1 C6 C7 -23.22(13) . . . . ?
O1 B1 C6 C11 -81.87(11) . . . . ?
O3 B1 C6 C11 43.62(13) . . . . ?
N1 B1 C6 C11 161.44(8) . . . . ?
C11 C6 C7 C8 -0.37(15) . . . . ?
B1 C6 C7 C8 -175.80(10) . . . . ?
C6 C7 C8 C9 0.28(17) . . . . ?
C7 C8 C9 C10 -0.04(17) . . . . ?
C8 C9 C10 C11 -0.10(16) . . . . ?
C9 C10 C11 C6 0.00(16) . . . . ?
C7 C6 C11 C10 0.23(15) . . . . ?
B1 C6 C11 C10 175.95(9) . . . . ?
O1 B2 C12 C13 -12.67(15) . . . . ?
O2 B2 C12 C13 167.63(10) . . . . ?
O1 B2 C12 C17 167.90(10) . . . . ?
O2 B2 C12 C17 -11.80(15) . . . . ?
C17 C12 C13 C14 1.59(16) . . . . ?
B2 C12 C13 C14 -177.86(10) . . . . ?
C12 C13 C14 C15 -1.42(17) . . . . ?
C13 C14 C15 C16 0.09(18) . . . . ?
C14 C15 C16 C17 0.99(18) . . . . ?
C15 C16 C17 C12 -0.79(17) . . . . ?
C13 C12 C17 C16 -0.48(16) . . . . ?
B2 C12 C17 C16 178.97(10) . . . . ?
O3 B3 C18 C19 177.47(10) . . . . ?
O2 B3 C18 C19 -4.70(16) . . . . ?
O3 B3 C18 C23 -1.04(16) . . . . ?
O2 B3 C18 C23 176.80(10) . . . . ?
C23 C18 C19 C20 -0.29(17) . . . . ?
B3 C18 C19 C20 -178.85(11) . . . . ?
C18 C19 C20 C21 -0.75(19) . . . . ?
C19 C20 C21 C22 1.22(19) . . . . ?
C20 C21 C22 C23 -0.66(19) . . . . ?
C21 C22 C23 C18 -0.40(19) . . . . ?
C19 C18 C23 C22 0.86(17) . . . . ?
B3 C18 C23 C22 179.42(11) . . . . ?
O2 B2 O1 B1 9.61(15) . . . . ?
C12 B2 O1 B1 -170.08(9) . . . . ?
O3 B1 O1 B2 -18.62(14) . . . . ?
C6 B1 O1 B2 105.82(11) . . . . ?
N1 B1 O1 B2 -136.44(9) . . . . ?
 
_refine_diff_density_max    0.165
_refine_diff_density_min   -0.180
_refine_diff_density_rms    0.033




