# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jianweipengsuanzhi
_database_code_depnum_ccdc_archive 'CCDC 2005208'
loop_
_audit_author_name
_audit_author_address
'Weilong Che'
;Tianjin University
China
;
_audit_update_record             
;
2020-05-22 deposited with the CCDC.	2020-08-26 downloaded from the CCDC.
;
_audit_creation_date             2020-05-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 B O3'
_chemical_formula_sum            'C19 H21 B O3'
_chemical_formula_weight         308.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H21 B O3'
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'
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/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                   6.3536(2)
_cell_length_b                   11.4414(4)
_cell_length_c                   23.5584(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.688(3)
_cell_angle_gamma                90
_cell_volume                     1710.67(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2557
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.1270
_cell_measurement_theta_min      5.4030
_shelx_estimated_absorpt_T_max   0.869
_shelx_estimated_absorpt_T_min   0.830
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73554
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.925
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5525
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         3.757
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -101.00 -19.00   1.00    1.34    --  -40.87 -57.00 120.00   82
  2  ω   -106.00 -62.00   1.00    1.34    --  -40.87-148.00 164.00   44
  3  ω      2.00  59.00   1.00    1.34    --   40.87 -57.00 -60.00   57
  4  ω     82.00 116.00   1.00    5.35    --  105.32-125.00-120.00   34
  5  ω     32.00 104.00   1.00    5.35    --  105.32-125.00  60.00   72
  6  ω    136.00 168.00   1.00    5.35    --  105.32 125.00 -60.00   32
  7  ω     63.00 128.00   1.00    5.35    --  105.32 -30.00  60.00   65
  8  ω     96.00 174.00   1.00    5.35    --  105.32 125.00-120.00   78
  9  ω    149.00 174.00   1.00    5.35    --  105.32 125.00  30.00   25
 10  ω     79.00 158.00   1.00    5.35    --  105.32  45.00 -60.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0309053000
_diffrn_orient_matrix_UB_12      -0.1328544000
_diffrn_orient_matrix_UB_13      0.0072112000
_diffrn_orient_matrix_UB_21      -0.0754645000
_diffrn_orient_matrix_UB_22      -0.0188054000
_diffrn_orient_matrix_UB_23      -0.0624394000
_diffrn_orient_matrix_UB_31      0.2284965000
_diffrn_orient_matrix_UB_32      0.0118161000
_diffrn_orient_matrix_UB_33      -0.0183385000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2459
_reflns_number_total             2875
_reflns_odcompleteness_completeness 93.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.060
_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     212
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0742
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1069P)²+1.0856P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1977
_refine_ls_wR_factor_ref         0.2074
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C19, C22
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C16, C23
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C17(H17),
 C18(H18)
3.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8532(4) 0.9667(2) 0.08990(9) 0.0422(5) Uani 1 1 d . . . . .
O2 O 0.8637(3) 0.56511(18) 0.17130(10) 0.0731(7) Uani 1 1 d . . . . .
C3 C 0.8388(4) 0.7742(2) 0.13357(10) 0.0457(6) Uani 1 1 d . . . . .
C4 C 0.9462(4) 0.8767(2) 0.12245(9) 0.0436(6) Uani 1 1 d . . . . .
H4 H 1.0838 0.8858 0.1371 0.052 Uiso 1 1 calc R . . . .
O5 O 1.1282(3) 0.68545(18) 0.19982(10) 0.0754(7) Uani 1 1 d . . . . .
C6 C 0.8875(4) 1.1812(2) 0.05472(10) 0.0454(6) Uani 1 1 d . . . . .
C7 C 0.6477(4) 0.9527(2) 0.06849(10) 0.0491(6) Uani 1 1 d . . . . .
H7 H 0.5833 1.0119 0.0469 0.059 Uiso 1 1 calc R . . . .
C8 C 0.5381(4) 0.8515(3) 0.07894(12) 0.0569(7) Uani 1 1 d . . . . .
H8 H 0.4002 0.8428 0.0645 0.068 Uiso 1 1 calc R . . . .
C9 C 0.6327(4) 0.7628(2) 0.11086(12) 0.0545(6) Uani 1 1 d . . . . .
H9 H 0.5579 0.6946 0.1173 0.065 Uiso 1 1 calc R . . . .
C10 C 0.9944(4) 1.2450(2) 0.01509(11) 0.0501(6) Uani 1 1 d . . . . .
H10 H 1.1214 1.2170 0.0024 0.060 Uiso 1 1 calc R . . . .
C11 C 0.9851(4) 1.0698(2) 0.07578(11) 0.0490(6) Uani 1 1 d . . . . .
B12 B 0.9454(5) 0.6733(3) 0.16906(11) 0.0462(6) Uani 1 1 d . . . . .
O13 O 1.1763(3) 1.0626(2) 0.08004(13) 0.0879(8) Uani 1 1 d . . . . .
C14 C 0.6996(5) 1.2247(3) 0.07373(13) 0.0630(8) Uani 1 1 d . . . . .
H14 H 0.6258 1.1830 0.1002 0.076 Uiso 1 1 calc R . . . .
C15 C 0.9146(5) 1.3491(3) -0.00559(13) 0.0642(8) Uani 1 1 d . . . . .
H15 H 0.9859 1.3903 -0.0328 0.077 Uiso 1 1 calc R . . . .
C16 C 1.0248(5) 0.4910(3) 0.19904(15) 0.0713(8) Uani 1 1 d . U . . .
C17 C 0.7307(6) 1.3919(3) 0.01371(18) 0.0820(10) Uani 1 1 d . . . . .
H17 H 0.6786 1.4630 0.0001 0.098 Uiso 1 1 calc R . . . .
C18 C 0.6219(6) 1.3307(3) 0.05311(17) 0.0818(10) Uani 1 1 d . . . . .
H18 H 0.4964 1.3602 0.0659 0.098 Uiso 1 1 calc R . . . .
C19 C 1.1513(5) 0.5793(3) 0.23466(14) 0.0702(8) Uani 1 1 d . U . . .
C20 C 1.3800(5) 0.5576(4) 0.24715(17) 0.0859(11) Uani 1 1 d . . . . .
H20A H 1.4525 0.5577 0.2123 0.129 Uiso 1 1 calc GR . . . .
H20B H 1.3983 0.4831 0.2655 0.129 Uiso 1 1 calc GR . . . .
H20C H 1.4366 0.6180 0.2717 0.129 Uiso 1 1 calc GR . . . .
C21 C 0.9219(6) 0.3936(3) 0.2292(2) 0.0903(12) Uani 1 1 d . . . . .
H21A H 0.8276 0.4251 0.2560 0.135 Uiso 1 1 calc GR . . . .
H21B H 1.0276 0.3471 0.2490 0.135 Uiso 1 1 calc GR . . . .
H21C H 0.8442 0.3457 0.2021 0.135 Uiso 1 1 calc GR . . . .
C22 C 1.0344(9) 0.6007(4) 0.29129(15) 0.1072(15) Uani 1 1 d . U . . .
H22A H 1.0988 0.6652 0.3115 0.161 Uiso 1 1 calc GR . . . .
H22B H 1.0443 0.5318 0.3145 0.161 Uiso 1 1 calc GR . . . .
H22C H 0.8888 0.6182 0.2823 0.161 Uiso 1 1 calc GR . . . .
C23 C 1.1678(10) 0.4421(4) 0.15143(19) 0.1188(17) Uani 1 1 d . U . . .
H23A H 1.0804 0.4077 0.1216 0.178 Uiso 1 1 calc GR . . . .
H23B H 1.2619 0.3840 0.1675 0.178 Uiso 1 1 calc GR . . . .
H23C H 1.2481 0.5049 0.1362 0.178 Uiso 1 1 calc GR . . . .


_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
C1 C4 1.398(3) . ?
C1 C7 1.387(3) . ?
C1 C11 1.492(3) . ?
O2 B12 1.345(4) . ?
O2 C16 1.460(4) . ?
C3 C4 1.388(3) . ?
C3 C9 1.398(4) . ?
C3 B12 1.560(4) . ?
O5 B12 1.347(3) . ?
O5 C19 1.469(3) . ?
C6 C10 1.387(4) . ?
C6 C11 1.493(3) . ?
C6 C14 1.387(4) . ?
C7 C8 1.380(4) . ?
C8 C9 1.383(4) . ?
C10 C15 1.375(4) . ?
C11 O13 1.217(3) . ?
C14 C18 1.388(4) . ?
C15 C17 1.364(5) . ?
C16 C19 1.519(5) . ?
C16 C21 1.489(4) . ?
C16 C23 1.579(6) . ?
C17 C18 1.375(5) . ?
C19 C20 1.490(5) . ?
C19 C22 1.576(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C1 C11 118.5(2) . . ?
C7 C1 C4 118.7(2) . . ?
C7 C1 C11 122.6(2) . . ?
B12 O2 C16 106.8(2) . . ?
C4 C3 C9 117.8(2) . . ?
C4 C3 B12 121.4(2) . . ?
C9 C3 B12 120.8(2) . . ?
C3 C4 C1 121.8(2) . . ?
B12 O5 C19 106.1(2) . . ?
C10 C6 C11 117.6(2) . . ?
C14 C6 C10 119.0(2) . . ?
C14 C6 C11 123.3(2) . . ?
C8 C7 C1 120.5(2) . . ?
C7 C8 C9 120.2(2) . . ?
C8 C9 C3 121.0(2) . . ?
C15 C10 C6 120.6(2) . . ?
C1 C11 C6 121.3(2) . . ?
O13 C11 C1 119.8(2) . . ?
O13 C11 C6 118.8(2) . . ?
O2 B12 C3 122.9(2) . . ?
O2 B12 O5 113.5(2) . . ?
O5 B12 C3 123.6(2) . . ?
C6 C14 C18 119.8(3) . . ?
C17 C15 C10 120.0(3) . . ?
O2 C16 C19 101.7(2) . . ?
O2 C16 C21 109.5(3) . . ?
O2 C16 C23 107.6(3) . . ?
C19 C16 C23 108.7(3) . . ?
C21 C16 C19 117.8(3) . . ?
C21 C16 C23 110.7(3) . . ?
C15 C17 C18 120.5(3) . . ?
C17 C18 C14 120.0(3) . . ?
O5 C19 C16 101.8(2) . . ?
O5 C19 C20 108.6(3) . . ?
O5 C19 C22 107.8(3) . . ?
C16 C19 C22 108.2(3) . . ?
C20 C19 C16 119.0(3) . . ?
C20 C19 C22 110.7(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 2.057
_oxdiff_exptl_absorpt_empirical_full_min 0.621
####################################################################### 
# 
# 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_danpelight
_database_code_depnum_ccdc_archive 'CCDC 2005210'
loop_
_audit_author_name
_audit_author_address
'Weilong Che'
;Tianjin University
China
;
_audit_update_record             
;
2020-05-22 deposited with the CCDC.	2020-08-26 downloaded from the CCDC.
;
_audit_creation_date             2019-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 B O3'
_chemical_formula_sum            'C19 H21 B O3'
_chemical_formula_weight         308.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H21 O3 B'
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'
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/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                   6.27903(10)
_cell_length_b                   10.62604(17)
_cell_length_c                   25.7596(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.8497(15)
_cell_angle_gamma                90
_cell_volume                     1717.81(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6717
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7710
_cell_measurement_theta_min      4.4840
_shelx_estimated_absorpt_T_max   0.842
_shelx_estimated_absorpt_T_min   0.793
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10687
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.057
_diffrn_reflns_theta_max         67.057
_diffrn_reflns_theta_min         3.433
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_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    -90.00 -12.00   1.00    5.07    --  -41.12 125.00  90.00   78
  2  ω   -110.00 -29.00   1.00    5.07    --  -41.12 -37.00 -90.00   81
  3  ω    -97.00 -71.00   1.00    5.07    --  -41.12-150.00 -31.00   26
  4  ω   -117.00  -9.00   1.00    5.07    --  -41.12 -77.00  30.00  108
  5  ω     -2.00  51.00   1.00    5.07    --   41.12 -37.00-180.00   53
  6  ω     79.00 105.00   1.00   20.29    --  105.32 150.00  13.00   26
  7  ω     76.00 106.00   1.00   20.29    --  105.32-125.00  90.00   30
  8  ω     43.00  86.00   1.00   20.29    --  105.32 -61.00 150.00   43
  9  ω     62.00 116.00   1.00   20.29    --  105.32-125.00-180.00   54
 10  ω    112.00 154.00   1.00   20.29    --  105.32  45.00-120.00   42
 11  ω     36.00  72.00   1.00   20.29    --  105.32-125.00  90.00   36
 12  ω     24.00 109.00   1.00   20.29    --  105.32 -94.00 -60.00   85
 13  ω     92.00 130.00   1.00   20.29    --  105.32 -45.00 120.00   38
 14  ω    129.00 170.00   1.00   20.29    --  105.32 150.00  13.00   41
 15  ω     46.00  72.00   1.00   20.29    --  105.32 -45.00 120.00   26
 16  ω     29.00 178.00   1.00   20.29    --  105.32   0.00-150.00  149
 17  ω     34.00 129.00   1.00   20.29    --  105.32 -45.00  30.00   95
 18  ω     33.00 116.00   1.00   20.29    --  105.32 -45.00 -90.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0120955000
_diffrn_orient_matrix_UB_12      -0.0241331000
_diffrn_orient_matrix_UB_13      -0.0588096000
_diffrn_orient_matrix_UB_21      -0.0249897000
_diffrn_orient_matrix_UB_22      -0.1423274000
_diffrn_orient_matrix_UB_23      0.0094183000
_diffrn_orient_matrix_UB_31      -0.2438699000
_diffrn_orient_matrix_UB_32      0.0134099000
_diffrn_orient_matrix_UB_33      -0.0058447000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2790
_reflns_number_total             3081
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3081
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.057
_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)+(0.0752P)²+0.3749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1382
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C13(H13), C15(H15), C16(H16), C18(H18),
 C20(H20)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C0AA(H0AA,H0AB,H0AC), C1AA(H1AA,
 H1AB,H1AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.60826(18) 0.86560(10) 0.19617(5) 0.0598(3) Uani 1 1 d . . . . .
O2 O 0.33957(18) 0.98212(10) 0.15934(5) 0.0615(3) Uani 1 1 d . . . . .
C3 C 0.3553(2) 0.52278(13) 0.12131(5) 0.0469(3) Uani 1 1 d . . . . .
H3 H 0.4352 0.4491 0.1218 0.056 Uiso 1 1 calc R . . . .
C4 C 0.3249(2) 0.74388(13) 0.14284(5) 0.0445(3) Uani 1 1 d . . . . .
C5 C 0.1518(2) 0.52396(13) 0.09809(5) 0.0449(3) Uani 1 1 d . . . . .
C6 C 0.1211(2) 0.74347(14) 0.11943(6) 0.0499(4) Uani 1 1 d . . . . .
H6 H 0.0421 0.8175 0.1183 0.060 Uiso 1 1 calc R . . . .
C7 C 0.4382(2) 0.63140(14) 0.14364(5) 0.0465(3) Uani 1 1 d . . . . .
H7 H 0.5732 0.6291 0.1596 0.056 Uiso 1 1 calc R . . . .
C8 C 0.0351(2) 0.63501(14) 0.09796(6) 0.0501(4) Uani 1 1 d . . . . .
H8 H -0.1022 0.6363 0.0833 0.060 Uiso 1 1 calc R . . . .
B9 B 0.4257(3) 0.86599(15) 0.16640(6) 0.0459(4) Uani 1 1 d . . . . .
C10 C 0.1801(2) 0.32063(14) 0.04343(6) 0.0490(4) Uani 1 1 d . . . . .
C11 C 0.0510(2) 0.40858(15) 0.07471(6) 0.0541(4) Uani 1 1 d . . . . .
O12 O -0.1376(2) 0.38887(14) 0.08071(7) 0.0896(5) Uani 1 1 d . . . . .
C13 C 0.3718(3) 0.35510(14) 0.02265(6) 0.0529(4) Uani 1 1 d . . . . .
H13 H 0.4274 0.4346 0.0298 0.063 Uiso 1 1 calc R . . . .
C14 C 0.6296(2) 0.99163(15) 0.21861(6) 0.0555(4) Uani 1 1 d . . . . .
C15 C 0.4035(3) 0.15710(18) -0.01912(8) 0.0720(5) Uani 1 1 d . . . . .
H15 H 0.4776 0.1022 -0.0401 0.086 Uiso 1 1 calc R . . . .
C16 C 0.4823(3) 0.27409(16) -0.00849(6) 0.0593(4) Uani 1 1 d . . . . .
H16 H 0.6107 0.2993 -0.0222 0.071 Uiso 1 1 calc R . . . .
C17 C 0.4977(3) 1.07254(15) 0.17939(7) 0.0609(4) Uani 1 1 d . . . . .
C18 C 0.1022(3) 0.20152(18) 0.03223(9) 0.0775(6) Uani 1 1 d . . . . .
H18 H -0.0265 0.1757 0.0456 0.093 Uiso 1 1 calc R . . . .
C19 C 0.8634(3) 1.0243(2) 0.22393(9) 0.0785(6) Uani 1 1 d . . . . .
H19A H 0.9321 0.9688 0.2487 0.118 Uiso 1 1 calc GR . . . .
H19B H 0.8788 1.1097 0.2356 0.118 Uiso 1 1 calc GR . . . .
H19C H 0.9280 1.0152 0.1909 0.118 Uiso 1 1 calc GR . . . .
C20 C 0.2147(4) 0.12096(19) 0.00127(11) 0.0952(8) Uani 1 1 d . . . . .
H20 H 0.1613 0.0409 -0.0058 0.114 Uiso 1 1 calc R . . . .
C21 C 0.5310(4) 0.9857(2) 0.27173(8) 0.0880(7) Uani 1 1 d . . . . .
H21A H 0.3828 0.9642 0.2677 0.132 Uiso 1 1 calc GR . . . .
H21B H 0.5448 1.0661 0.2885 0.132 Uiso 1 1 calc GR . . . .
H21C H 0.6030 0.9229 0.2926 0.132 Uiso 1 1 calc GR . . . .
C0AA C 0.6255(5) 1.1141(2) 0.13295(9) 0.0982(8) Uani 1 1 d . . . . .
H0AA H 0.7054 1.0440 0.1204 0.147 Uiso 1 1 calc GR . . . .
H0AB H 0.7215 1.1803 0.1434 0.147 Uiso 1 1 calc GR . . . .
H0AC H 0.5299 1.1440 0.1059 0.147 Uiso 1 1 calc GR . . . .
C1AA C 0.3827(4) 1.18359(19) 0.20175(12) 0.0958(8) Uani 1 1 d . . . . .
H1AA H 0.2934 1.2217 0.1752 0.144 Uiso 1 1 calc GR . . . .
H1AB H 0.4849 1.2441 0.2147 0.144 Uiso 1 1 calc GR . . . .
H1AC H 0.2966 1.1558 0.2297 0.144 Uiso 1 1 calc GR . . . .


_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 B9 1.358(2) . ?
O1 C14 1.4632(18) . ?
O2 B9 1.357(2) . ?
O2 C17 1.4636(18) . ?
C3 C5 1.393(2) . ?
C3 C7 1.384(2) . ?
C4 C6 1.397(2) . ?
C4 C7 1.391(2) . ?
C4 B9 1.558(2) . ?
C5 C8 1.389(2) . ?
C5 C11 1.497(2) . ?
C6 C8 1.381(2) . ?
C10 C11 1.491(2) . ?
C10 C13 1.383(2) . ?
C10 C18 1.384(2) . ?
C11 O12 1.2170(19) . ?
C13 C16 1.379(2) . ?
C14 C17 1.547(2) . ?
C14 C19 1.510(2) . ?
C14 C21 1.521(2) . ?
C15 C16 1.363(2) . ?
C15 C20 1.367(3) . ?
C17 C0AA 1.527(3) . ?
C17 C1AA 1.507(3) . ?
C18 C20 1.380(3) . ?

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
B9 O1 C14 106.58(12) . . ?
B9 O2 C17 106.67(12) . . ?
C7 C3 C5 119.92(13) . . ?
C6 C4 B9 121.70(13) . . ?
C7 C4 C6 117.69(13) . . ?
C7 C4 B9 120.59(12) . . ?
C3 C5 C11 122.37(13) . . ?
C8 C5 C3 119.03(13) . . ?
C8 C5 C11 118.57(13) . . ?
C8 C6 C4 121.10(14) . . ?
C3 C7 C4 121.67(13) . . ?
C6 C8 C5 120.56(13) . . ?
O1 B9 C4 122.82(14) . . ?
O2 B9 O1 113.81(13) . . ?
O2 B9 C4 123.37(13) . . ?
C13 C10 C11 122.60(13) . . ?
C13 C10 C18 117.90(15) . . ?
C18 C10 C11 119.43(14) . . ?
C10 C11 C5 120.02(12) . . ?
O12 C11 C5 119.37(14) . . ?
O12 C11 C10 120.60(14) . . ?
C16 C13 C10 121.37(14) . . ?
O1 C14 C17 102.13(12) . . ?
O1 C14 C19 108.83(14) . . ?
O1 C14 C21 106.41(14) . . ?
C19 C14 C17 115.47(16) . . ?
C19 C14 C21 110.54(16) . . ?
C21 C14 C17 112.67(16) . . ?
C16 C15 C20 119.52(17) . . ?
C15 C16 C13 120.01(16) . . ?
O2 C17 C14 102.04(12) . . ?
O2 C17 C0AA 106.32(15) . . ?
O2 C17 C1AA 108.73(15) . . ?
C0AA C17 C14 112.84(17) . . ?
C1AA C17 C14 116.01(17) . . ?
C1AA C17 C0AA 110.09(19) . . ?
C20 C18 C10 120.24(17) . . ?
C15 C20 C18 120.96(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.257
_oxdiff_exptl_absorpt_empirical_full_min 0.785
####################################################################### 
# 
# 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_danfumed
_database_code_depnum_ccdc_archive 'CCDC 2005209'
loop_
_audit_author_name
_audit_author_address
'Weilong Che'
;Tianjin University
China
;
_audit_update_record             
;
2020-05-22 deposited with the CCDC.	2020-08-26 downloaded from the CCDC.
;
_audit_creation_date             2019-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 B O3'
_chemical_formula_sum            'C19 H21 B O3'
_chemical_formula_weight         308.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 O3 B H21'
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'
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                   12.4558(2)
_cell_length_b                   12.11252(15)
_cell_length_c                   12.7411(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.325(2)
_cell_angle_gamma                90
_cell_volume                     1765.17(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6751
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8200
_cell_measurement_theta_min      5.2280
_shelx_estimated_absorpt_T_max   0.841
_shelx_estimated_absorpt_T_min   0.792
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11621
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.071
_diffrn_reflns_theta_max         67.071
_diffrn_reflns_theta_min         3.865
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_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   -116.00 -91.00   1.00    4.23    --  -41.12 -37.00-120.00   25
  2  ω    -80.00 -17.00   1.00    4.23    --  -41.12 -37.00-120.00   63
  3  ω   -121.00  -4.00   1.00    4.23    --  -41.12 -19.00 120.00  117
  4  ω      7.00  66.00   1.00    4.23    --   41.12 -57.00 120.00   59
  5  ω     23.00  96.00   1.00    4.23    --   41.12-125.00  30.00   73
  6  ω    -23.00  33.00   1.00    4.23    --   41.12 -37.00  30.00   56
  7  ω     35.00 104.00   1.00   16.93    --  105.32 -94.00 120.00   69
  8  ω     80.00 166.00   1.00   16.93    --  105.32  45.00  30.00   86
  9  ω     83.00 128.00   1.00   16.93    --  105.32  61.00-120.00   45
 10  ω     36.00  61.00   1.00   16.93    --  105.32 -94.00-120.00   25
 11  ω     90.00 158.00   1.00   16.93    --  105.32 -15.00 -30.00   68
 12  ω     45.00 138.00   1.00   16.93    --  105.32 -77.00 -60.00   93
 13  ω     73.00 104.00   1.00   16.93    --  105.32-125.00-120.00   31
 14  ω     73.00 176.00   1.00   16.93    --  105.32  77.00  60.00  103
 15  ω    100.00 175.00   1.00   16.93    --  105.32  77.00-150.00   75
 16  ω     40.00 128.00   1.00   16.93    --  105.32 -45.00  90.00   88
 17  ω     41.00 117.00   1.00   16.93    --  105.32-125.00 -60.00   76
 18  ω     83.00 108.00   1.00   16.93    --  105.32-115.00  68.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1114896000
_diffrn_orient_matrix_UB_12      0.0486643000
_diffrn_orient_matrix_UB_13      0.0930046000
_diffrn_orient_matrix_UB_21      0.0558843000
_diffrn_orient_matrix_UB_22      -0.1157765000
_diffrn_orient_matrix_UB_23      0.0228465000
_diffrn_orient_matrix_UB_31      0.0510438000
_diffrn_orient_matrix_UB_32      0.0207628000
_diffrn_orient_matrix_UB_33      -0.0902211000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2781
_reflns_number_total             3144
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0805
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1355P)²+0.6493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2187
_refine_ls_wR_factor_ref         0.2267
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C14(H14), C15(H15), C16(H16),
 C18(H18)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C0AA(H0AA,H0AB,H0AC), C1AA(H1AA,
 H1AB,H1AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.49795(15) 0.65399(16) 0.08796(15) 0.0719(5) Uani 1 1 d . . . . .
O2 O 0.43034(16) 0.68002(15) 0.22753(14) 0.0698(5) Uani 1 1 d . . . . .
C3 C 0.31202(17) 0.77047(17) 0.03374(17) 0.0495(5) Uani 1 1 d . . . . .
C4 C 0.12925(19) 0.90046(17) -0.11688(18) 0.0516(5) Uani 1 1 d . . . . .
C5 C 0.30284(18) 0.79192(18) -0.07700(18) 0.0542(5) Uani 1 1 d . . . . .
H5 H 0.3586 0.7632 -0.1010 0.065 Uiso 1 1 calc R . . . .
C6 C 0.1379(2) 0.88075(19) -0.00641(19) 0.0559(5) Uani 1 1 d . . . . .
H6 H 0.0836 0.9116 0.0182 0.067 Uiso 1 1 calc R . . . .
C7 C 0.2125(2) 0.85500(19) -0.15188(18) 0.0555(6) Uani 1 1 d . . . . .
H7 H 0.2073 0.8672 -0.2258 0.067 Uiso 1 1 calc R . . . .
C8 C 0.2265(2) 0.81596(18) 0.06657(18) 0.0542(5) Uani 1 1 d . . . . .
H8 H 0.2298 0.8019 0.1396 0.065 Uiso 1 1 calc R . . . .
C9 C 0.0342(2) 0.97455(19) -0.1931(2) 0.0587(6) Uani 1 1 d . . . . .
B10 B 0.4144(2) 0.6999(2) 0.1180(2) 0.0536(6) Uani 1 1 d . . . . .
C11 C -0.02878(19) 0.94692(18) -0.3160(2) 0.0545(5) Uani 1 1 d . . . . .
C12 C -0.0354(2) 0.8395(2) -0.3573(2) 0.0643(6) Uani 1 1 d . . . . .
H12 H 0.0028 0.7827 -0.3074 0.077 Uiso 1 1 calc R . . . .
O13 O 0.0077(2) 1.05705(17) -0.15342(17) 0.0892(7) Uani 1 1 d . . . . .
C14 C -0.0871(2) 1.0305(2) -0.3926(2) 0.0630(6) Uani 1 1 d . . . . .
H14 H -0.0848 1.1024 -0.3662 0.076 Uiso 1 1 calc R . . . .
C15 C -0.1479(2) 1.0081(2) -0.5067(2) 0.0723(7) Uani 1 1 d . . . . .
H15 H -0.1859 1.0646 -0.5571 0.087 Uiso 1 1 calc R . . . .
C16 C -0.0978(2) 0.8167(2) -0.4709(3) 0.0771(8) Uani 1 1 d . . . . .
H16 H -0.1035 0.7445 -0.4972 0.093 Uiso 1 1 calc R . . . .
C17 C 0.5267(2) 0.6021(2) 0.2746(2) 0.0726(7) Uani 1 1 d . . . . .
C18 C -0.1522(2) 0.9013(2) -0.5464(3) 0.0794(8) Uani 1 1 d . . . . .
H18 H -0.1918 0.8862 -0.6238 0.095 Uiso 1 1 calc R . . . .
C19 C 0.5877(2) 0.6087(3) 0.1901(2) 0.0770(8) Uani 1 1 d . . . . .
C21 C 0.6862(3) 0.6964(4) 0.2244(4) 0.1199(14) Uani 1 1 d . . . . .
H21A H 0.7063 0.7113 0.1603 0.180 Uiso 1 1 calc GR . . . .
H21B H 0.7538 0.6691 0.2870 0.180 Uiso 1 1 calc GR . . . .
H21C H 0.6597 0.7632 0.2470 0.180 Uiso 1 1 calc GR . . . .
C23 C 0.6017(4) 0.6336(5) 0.3938(3) 0.141(2) Uani 1 1 d . . . . .
H23A H 0.6244 0.7096 0.3958 0.211 Uiso 1 1 calc GR . . . .
H23B H 0.6703 0.5879 0.4212 0.211 Uiso 1 1 calc GR . . . .
H23C H 0.5590 0.6237 0.4415 0.211 Uiso 1 1 calc GR . . . .
C0AA C 0.6359(4) 0.5055(4) 0.1602(3) 0.1346(18) Uani 1 1 d . . . . .
H0AA H 0.5751 0.4511 0.1316 0.202 Uiso 1 1 calc GR . . . .
H0AB H 0.6983 0.4774 0.2271 0.202 Uiso 1 1 calc GR . . . .
H0AC H 0.6652 0.5219 0.1027 0.202 Uiso 1 1 calc GR . . . .
C1AA C 0.4673(4) 0.4911(4) 0.2667(6) 0.169(3) Uani 1 1 d . . . . .
H1AA H 0.4873 0.4619 0.3421 0.253 Uiso 1 1 calc GR . . . .
H1AB H 0.4931 0.4410 0.2230 0.253 Uiso 1 1 calc GR . . . .
H1AC H 0.3841 0.5002 0.2298 0.253 Uiso 1 1 calc GR . . . .


_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 B10 1.361(3) . ?
O1 C19 1.447(3) . ?
O2 B10 1.351(3) . ?
O2 C17 1.456(3) . ?
C3 C5 1.394(3) . ?
C3 C8 1.402(3) . ?
C3 B10 1.558(3) . ?
C4 C6 1.389(3) . ?
C4 C7 1.394(3) . ?
C4 C9 1.497(3) . ?
C5 C7 1.382(3) . ?
C6 C8 1.373(3) . ?
C9 C11 1.485(3) . ?
C9 O13 1.223(3) . ?
C11 C12 1.393(3) . ?
C11 C14 1.395(3) . ?
C12 C16 1.373(4) . ?
C14 C15 1.374(4) . ?
C15 C18 1.382(4) . ?
C16 C18 1.384(4) . ?
C17 C19 1.546(4) . ?
C17 C23 1.484(5) . ?
C17 C1AA 1.519(5) . ?
C19 C21 1.550(5) . ?
C19 C0AA 1.501(4) . ?

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
B10 O1 C19 107.82(19) . . ?
B10 O2 C17 107.53(19) . . ?
C5 C3 C8 117.46(19) . . ?
C5 C3 B10 121.10(19) . . ?
C8 C3 B10 121.43(19) . . ?
C6 C4 C7 119.1(2) . . ?
C6 C4 C9 119.02(19) . . ?
C7 C4 C9 121.77(19) . . ?
C7 C5 C3 121.32(19) . . ?
C8 C6 C4 120.3(2) . . ?
C5 C7 C4 120.2(2) . . ?
C6 C8 C3 121.6(2) . . ?
C11 C9 C4 120.07(18) . . ?
O13 C9 C4 119.7(2) . . ?
O13 C9 C11 120.2(2) . . ?
O1 B10 C3 122.6(2) . . ?
O2 B10 O1 113.7(2) . . ?
O2 B10 C3 123.7(2) . . ?
C12 C11 C9 122.4(2) . . ?
C12 C11 C14 118.5(2) . . ?
C14 C11 C9 119.1(2) . . ?
C16 C12 C11 120.7(2) . . ?
C15 C14 C11 120.9(2) . . ?
C14 C15 C18 119.8(2) . . ?
C12 C16 C18 120.1(3) . . ?
O2 C17 C19 103.4(2) . . ?
O2 C17 C23 109.7(3) . . ?
O2 C17 C1AA 104.3(2) . . ?
C23 C17 C19 114.5(3) . . ?
C23 C17 C1AA 112.9(4) . . ?
C1AA C17 C19 111.1(4) . . ?
C15 C18 C16 120.1(3) . . ?
O1 C19 C17 103.2(2) . . ?
O1 C19 C21 103.7(3) . . ?
O1 C19 C0AA 109.4(2) . . ?
C17 C19 C21 113.1(3) . . ?
C0AA C19 C17 119.4(3) . . ?
C0AA C19 C21 106.9(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.114
_oxdiff_exptl_absorpt_empirical_full_min 0.656
####################################################################### 
# 
# 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_2wei-pengsuanzhi
_database_code_depnum_ccdc_archive 'CCDC 2005211'
loop_
_audit_author_name
_audit_author_address
'Weilong Che'
;Tianjin University
China
;
_audit_update_record             
;
2020-05-22 deposited with the CCDC.	2020-08-26 downloaded from the CCDC.
;
_audit_creation_date             2020-04-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 B O3'
_chemical_formula_sum            'C19 H21 B O3'
_chemical_formula_weight         308.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H21 O3 B'
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'
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                   8.73519(9)
_cell_length_b                   9.35255(9)
_cell_length_c                   21.1327(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.4281(10)
_cell_angle_gamma                90
_cell_volume                     1692.23(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9434
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.1010
_cell_measurement_theta_min      4.2450
_shelx_estimated_absorpt_T_max   0.839
_shelx_estimated_absorpt_T_min   0.790
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0120
_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       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13713
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.068
_diffrn_reflns_theta_max         67.067
_diffrn_reflns_theta_min         4.269
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_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   -117.00 -14.00   1.00    1.52    --  -41.12 -77.00  60.00  103
  2  ω    -44.00  31.00   1.00    1.52    --  -41.12  37.00   0.00   75
  3  ω     23.00  66.00   1.00    1.52    --   41.12  37.00 150.00   43
  4  ω     10.00  56.00   1.00    1.52    --   41.12  77.00-180.00   46
  5  ω    -31.00  43.00   1.00    1.52    --   41.12 -37.00  60.00   74
  6  ω     29.00  72.00   1.00    1.52    --   41.12  57.00-180.00   43
  7  ω     26.00  87.00   1.00    1.52    --   41.12-125.00  90.00   61
  8  ω     77.00 102.00   1.00    6.07    --  105.32  61.00  90.00   25
  9  ω     76.00 122.00   1.00    6.07    --  105.32  61.00 150.00   46
 10  ω    124.00 150.00   1.00    6.07    --  105.32  61.00-180.00   26
 11  ω     79.00 106.00   1.00    6.07    --  105.32  45.00 150.00   27
 12  ω     79.00 111.00   1.00    6.07    --  105.32  45.00-180.00   32
 13  ω     81.00 107.00   1.00    6.07    --  105.32  45.00 120.00   26
 14  ω     76.00 102.00   1.00    6.07    --  105.32  61.00 120.00   26
 15  ω    112.00 177.00   1.00    6.07    --  105.32  77.00  90.00   65
 16  ω     73.00 100.00   1.00    6.07    --  105.32  77.00  90.00   27
 17  ω     76.00 103.00   1.00    6.07    --  105.32  61.00-180.00   27
 18  ω     73.00  99.00   1.00    6.07    --  105.32  77.00 150.00   26
 19  ω     99.00 124.00   1.00    6.07    --  105.32 125.00 -90.00   25
 20  ω    140.00 177.00   1.00    6.07    --  105.32 125.00 -90.00   37
 21  ω     73.00 103.00   1.00    6.07    --  105.32  77.00  60.00   30
 22  ω    108.00 173.00   1.00    6.07    --  105.32  77.00  60.00   65
 23  ω     74.00  99.00   1.00    6.07    --  105.32  77.00 120.00   25
 24  ω     73.00  99.00   1.00    6.07    --  105.32  77.00-180.00   26
 25  ω     77.00 103.00   1.00    6.07    --  105.32  30.00-150.00   26
 26  ω     81.00 165.00   1.00    6.07    --  105.32  45.00-150.00   84
 27  ω    126.00 151.00   1.00    6.07    --  105.32  61.00 120.00   25
 28  ω     95.00 168.00   1.00    6.07    --  105.32 125.00-150.00   73
 29  ω     82.00 109.00   1.00    6.07    --  105.32  45.00  90.00   27
 30  ω     23.00  85.00   1.00    6.07    --  105.32 -94.00  60.00   62
 31  ω     67.00 117.00   1.00    6.07    --  105.32-125.00 -30.00   50
 32  ω     96.00 172.00   1.00    6.07    --  105.32 125.00 120.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0218942000
_diffrn_orient_matrix_UB_12      -0.0457368000
_diffrn_orient_matrix_UB_13      -0.0676737000
_diffrn_orient_matrix_UB_21      -0.1713241000
_diffrn_orient_matrix_UB_22      0.0394014000
_diffrn_orient_matrix_UB_23      -0.0279592000
_diffrn_orient_matrix_UB_31      0.0505502000
_diffrn_orient_matrix_UB_32      0.1532329000
_diffrn_orient_matrix_UB_33      -0.0130183000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2850
_reflns_number_total             3035
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3035
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.064
_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)+(0.0610P)²+0.3112P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1088
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C19(H19), C12(H12), C21(H21), C23(H23), C20(H20),
 C22(H22), C13(H13)
2.b Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C5(H5a,H5b,H5c), C1(H1a,H1b,H1c), C3(H3a,H3b,H3c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O8 O 0.30098(10) 0.77405(9) 0.18321(4) 0.0408(2) Uani 1 1 d . . . . .
O6 O 0.38805(11) 1.00412(9) 0.19239(4) 0.0470(2) Uani 1 1 d . . . . .
O17 O 0.13602(10) 0.88491(11) 0.05572(5) 0.0522(3) Uani 1 1 d . . . . .
C11 C 0.62055(15) 0.88298(14) 0.10788(6) 0.0444(3) Uani 1 1 d . . . . .
H11 H 0.6750 0.9140 0.1479 0.053 Uiso 1 1 calc R . . . .
C18 C 0.12002(14) 0.71391(13) -0.02687(6) 0.0386(3) Uani 1 1 d . . . . .
C16 C 0.20754(14) 0.80803(13) 0.02497(6) 0.0391(3) Uani 1 1 d . . . . .
C15 C 0.38152(14) 0.81250(13) 0.03822(6) 0.0385(3) Uani 1 1 d . . . . .
C14 C 0.46247(16) 0.78958(16) -0.01123(7) 0.0496(3) Uani 1 1 d . . . . .
H14 H 0.4097 0.7569 -0.0512 0.060 Uiso 1 1 calc R . . . .
C10 C 0.45994(13) 0.85886(12) 0.09924(6) 0.0371(3) Uani 1 1 d . . . . .
C2 C 0.23238(14) 0.83789(13) 0.23429(6) 0.0400(3) Uani 1 1 d . . . . .
C4 C 0.33734(15) 0.97167(14) 0.25279(6) 0.0437(3) Uani 1 1 d . . . . .
B1 B 0.37536(15) 0.88077(14) 0.15747(6) 0.0361(3) Uani 1 1 d . . . . .
C19 C -0.01752(14) 0.76516(15) -0.06466(6) 0.0441(3) Uani 1 1 d . . . . .
H19 H -0.0491 0.8587 -0.0595 0.053 Uiso 1 1 calc R . . . .
C12 C 0.70049(15) 0.86171(16) 0.05820(7) 0.0521(3) Uani 1 1 d . . . . .
H12 H 0.8074 0.8788 0.0650 0.063 Uiso 1 1 calc R . . . .
C21 C -0.06348(19) 0.53717(18) -0.11666(7) 0.0603(4) Uani 1 1 d . . . . .
H21 H -0.1259 0.4775 -0.1463 0.072 Uiso 1 1 calc R . . . .
C23 C 0.16623(16) 0.57393(15) -0.03527(6) 0.0485(3) Uani 1 1 d . . . . .
H23 H 0.2598 0.5396 -0.0112 0.058 Uiso 1 1 calc R . . . .
C20 C -0.10759(16) 0.67738(18) -0.11000(7) 0.0550(4) Uani 1 1 d . . . . .
H20 H -0.1980 0.7128 -0.1361 0.066 Uiso 1 1 calc R . . . .
C22 C 0.07272(19) 0.48596(16) -0.07948(7) 0.0580(4) Uani 1 1 d . . . . .
H22 H 0.1022 0.3916 -0.0841 0.070 Uiso 1 1 calc R . . . .
C7 C 0.06378(16) 0.87509(18) 0.20456(8) 0.0561(4) Uani 1 1 d . . . . .
H7A H 0.0620 0.9480 0.1724 0.084 Uiso 1 1 calc GR . . . .
H7B H 0.0119 0.9094 0.2376 0.084 Uiso 1 1 calc GR . . . .
H7C H 0.0112 0.7914 0.1849 0.084 Uiso 1 1 calc GR . . . .
C13 C 0.62175(17) 0.81529(18) -0.00109(7) 0.0574(4) Uani 1 1 d . . . . .
H13 H 0.6754 0.8011 -0.0344 0.069 Uiso 1 1 calc R . . . .
C5 C 0.2554(2) 1.10219(16) 0.27201(8) 0.0650(4) Uani 1 1 d . . . . .
H5A H 0.3283 1.1798 0.2810 0.098 Uiso 1 1 calc GR . . . .
H5B H 0.2142 1.0811 0.3099 0.098 Uiso 1 1 calc GR . . . .
H5C H 0.1715 1.1286 0.2373 0.098 Uiso 1 1 calc GR . . . .
C1 C 0.23760(19) 0.72906(16) 0.28770(7) 0.0562(4) Uani 1 1 d . . . . .
H1A H 0.1711 0.6498 0.2719 0.084 Uiso 1 1 calc GR . . . .
H1B H 0.2022 0.7726 0.3234 0.084 Uiso 1 1 calc GR . . . .
H1C H 0.3428 0.6957 0.3017 0.084 Uiso 1 1 calc GR . . . .
C3 C 0.48429(19) 0.9396(2) 0.30285(8) 0.0702(5) Uani 1 1 d . . . . .
H3A H 0.5319 0.8537 0.2910 0.105 Uiso 1 1 calc GR . . . .
H3B H 0.4573 0.9271 0.3444 0.105 Uiso 1 1 calc GR . . . .
H3C H 0.5563 1.0177 0.3047 0.105 Uiso 1 1 calc GR . . . .


_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
O8 C2 1.4619(14) . ?
O8 B1 1.3617(16) . ?
O6 C4 1.4634(14) . ?
O6 B1 1.3620(16) . ?
O17 C16 1.2208(14) . ?
C11 C10 1.3968(17) . ?
C11 C12 1.3857(19) . ?
C18 C16 1.4926(17) . ?
C18 C19 1.3896(18) . ?
C18 C23 1.3916(18) . ?
C16 C15 1.4904(17) . ?
C15 C14 1.3896(17) . ?
C15 C10 1.4035(17) . ?
C14 C13 1.386(2) . ?
C10 B1 1.5693(17) . ?
C2 C4 1.5546(17) . ?
C2 C7 1.5226(19) . ?
C2 C1 1.5137(18) . ?
C4 C5 1.511(2) . ?
C4 C3 1.523(2) . ?
C19 C20 1.383(2) . ?
C12 C13 1.375(2) . ?
C21 C20 1.382(2) . ?
C21 C22 1.375(2) . ?
C23 C22 1.384(2) . ?

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 O8 C2 107.06(9) . . ?
B1 O6 C4 106.90(9) . . ?
C12 C11 C10 121.44(12) . . ?
C19 C18 C16 118.51(11) . . ?
C19 C18 C23 119.39(12) . . ?
C23 C18 C16 121.95(11) . . ?
O17 C16 C18 119.76(11) . . ?
O17 C16 C15 119.59(11) . . ?
C15 C16 C18 120.62(10) . . ?
C14 C15 C16 120.42(11) . . ?
C14 C15 C10 120.68(11) . . ?
C10 C15 C16 118.37(10) . . ?
C13 C14 C15 120.11(13) . . ?
C11 C10 C15 117.69(11) . . ?
C11 C10 B1 119.54(11) . . ?
C15 C10 B1 122.75(10) . . ?
O8 C2 C4 101.93(9) . . ?
O8 C2 C7 107.04(10) . . ?
O8 C2 C1 108.64(10) . . ?
C7 C2 C4 113.20(11) . . ?
C1 C2 C4 115.12(11) . . ?
C1 C2 C7 110.19(11) . . ?
O6 C4 C2 102.30(9) . . ?
O6 C4 C5 107.96(11) . . ?
O6 C4 C3 106.72(11) . . ?
C5 C4 C2 115.50(12) . . ?
C5 C4 C3 110.59(13) . . ?
C3 C4 C2 112.95(12) . . ?
O8 B1 O6 113.48(11) . . ?
O8 B1 C10 123.61(11) . . ?
O6 B1 C10 122.35(11) . . ?
C20 C19 C18 120.13(13) . . ?
C13 C12 C11 119.98(12) . . ?
C22 C21 C20 119.96(14) . . ?
C22 C23 C18 119.88(13) . . ?
C21 C20 C19 120.14(14) . . ?
C21 C22 C23 120.44(14) . . ?
C12 C13 C14 120.09(13) . . ?

_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 1.118
_oxdiff_exptl_absorpt_empirical_full_min 0.896
