# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_20230308-sw-11
_database_code_depnum_ccdc_archive 'CCDC 2269472'
loop_
_audit_author_name
_audit_author_address
'Lin Guo'
;Harbin Institute of Technology (Shenzhen)
China
;
_audit_update_record             
;
2023-06-13 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_audit_creation_date             2023-03-09
_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         'C20 H22 B P'
_chemical_formula_sum            'C20 H22 B P'
_chemical_formula_weight         304.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H P 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'
P P 0.2955 0.4335 '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                   6.76040(10)
_cell_length_b                   16.4043(3)
_cell_length_c                   15.8328(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.946(2)
_cell_angle_gamma                90
_cell_volume                     1746.40(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7208
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      75.9870
_cell_measurement_theta_min      2.6630
_shelx_estimated_absorpt_T_max   0.891
_shelx_estimated_absorpt_T_min   0.837
_exptl_absorpt_coefficient_mu    1.313
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10413
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         3.891
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  26.00   0.50    0.05    --  -46.72  49.00 -63.00  164
  2  ω   -110.00 -31.00   0.50    0.07    --  -95.00  49.00 -63.00  158
  3  ω   -159.00 -87.00   0.50    0.07    --  -95.00 -94.00 -90.00  144
  4  ω   -143.00 -80.00   0.50    0.07    --  -95.00 -49.00 148.00  126
  5  ω   -119.00 -53.00   0.50    0.05    --  -46.72 -49.00 148.00  132
  6  ω     72.00  98.00   0.50    0.05    --   46.72  49.00 -63.00   52
  7  ω     98.00 129.00   0.50    0.07    --  107.00  49.00 -63.00   62
  8  ω    100.00 159.00   0.50    0.07    --  107.00  15.00 -30.00  118
  9  ω     92.00 160.00   0.50    0.07    --  107.00  30.00  30.00  136
 10  ω     91.00 158.00   0.50    0.07    --  107.00  15.00  90.00  134
 11  ω     69.00  95.00   0.50    0.07    --  107.00 -94.00 -30.00   52
 12  ω     75.00 101.00   0.50    0.07    --  107.00 -94.00   0.00   52
 13  ω     36.00  68.00   0.50    0.07    --  107.00 -94.00 -30.00   64
 14  ω     40.00  66.00   0.50    0.07    --  107.00 -94.00   0.00   52
 15  ω     47.00 110.00   0.50    0.07    --  107.00-125.00 150.00  126
 16  ω    -24.00  32.00   0.50    0.05    --   46.72 -49.00 148.00  112
 17  ω     34.00  59.00   0.50    0.07    --  107.00 -49.00 148.00   50
 18  ω     20.00  90.00   0.50    0.05    --   46.72-125.00   0.00  140
;
_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      -0.0936875000
_diffrn_orient_matrix_UB_12      -0.0417087000
_diffrn_orient_matrix_UB_13      -0.0818086000
_diffrn_orient_matrix_UB_21      0.2027739000
_diffrn_orient_matrix_UB_22      -0.0382362000
_diffrn_orient_matrix_UB_23      -0.0129018000
_diffrn_orient_matrix_UB_31      -0.0517441000
_diffrn_orient_matrix_UB_32      -0.0749252000
_diffrn_orient_matrix_UB_33      0.0520113000
_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                2732
_reflns_number_total             3073
_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 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3073
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0981P)²+0.5739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1532
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
1.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C18(H18), C19(H19), C20(H20)
1.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_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
P1 P 0.36895(7) 0.53149(3) 0.84132(3) 0.0274(2) Uani 1 1 d . . . . .
C1 C 0.2707(3) 0.55264(11) 0.73250(12) 0.0286(4) Uani 1 1 d . . . . .
C2 C 0.3933(3) 0.58689(13) 0.67705(14) 0.0415(5) Uani 1 1 d . . . . .
H2 H 0.525022 0.598835 0.695896 0.050 Uiso 1 1 calc R U . . .
C3 C 0.3209(4) 0.60334(16) 0.59397(16) 0.0529(6) Uani 1 1 d . . . . .
H3 H 0.403688 0.626953 0.557453 0.063 Uiso 1 1 calc R U . . .
C4 C 0.1271(4) 0.58505(13) 0.56489(14) 0.0458(6) Uani 1 1 d . . . . .
H4 H 0.079073 0.596297 0.508925 0.055 Uiso 1 1 calc R U . . .
C5 C 0.0046(3) 0.55001(13) 0.61898(14) 0.0409(5) Uani 1 1 d . . . . .
H5 H -0.125911 0.536951 0.599172 0.049 Uiso 1 1 calc R U . . .
C6 C 0.0744(3) 0.53411(11) 0.70267(14) 0.0345(5) Uani 1 1 d . . . . .
H6 H -0.009591 0.511045 0.739027 0.041 Uiso 1 1 calc R U . . .
C8 C 0.2854(3) 0.42851(12) 0.86061(12) 0.0324(4) Uani 1 1 d . . . . .
C9 C 0.1170(3) 0.41050(12) 0.89999(14) 0.0382(5) Uani 1 1 d . . . . .
H9 H 0.044396 0.452247 0.921870 0.046 Uiso 1 1 calc R U . . .
C10 C 0.0566(4) 0.32998(14) 0.90675(16) 0.0528(6) Uani 1 1 d . . . . .
H10 H -0.055463 0.317897 0.933894 0.063 Uiso 1 1 calc R U . . .
C11 C 0.1610(5) 0.26855(14) 0.87369(17) 0.0609(8) Uani 1 1 d . . . . .
H11 H 0.118685 0.214873 0.877641 0.073 Uiso 1 1 calc R U . . .
C12 C 0.3273(5) 0.28561(15) 0.8349(2) 0.0679(8) Uani 1 1 d . . . . .
H12 H 0.398237 0.243484 0.812793 0.081 Uiso 1 1 calc R U . . .
C13 C 0.3908(4) 0.36553(14) 0.82823(17) 0.0526(7) Uani 1 1 d . . . . .
H13 H 0.504552 0.376805 0.801948 0.063 Uiso 1 1 calc R U . . .
C14 C 0.2355(3) 0.59932(11) 0.90784(12) 0.0309(4) Uani 1 1 d . . . . .
H14A H 0.094621 0.586878 0.899364 0.037 Uiso 1 1 calc R U . . .
H14B H 0.281028 0.589347 0.967063 0.037 Uiso 1 1 calc R U . . .
C15 C 0.2660(3) 0.68837(11) 0.88797(12) 0.0305(4) Uani 1 1 d . . . . .
C16 C 0.4428(3) 0.72811(12) 0.91582(12) 0.0343(5) Uani 1 1 d . . . . .
H16 H 0.542757 0.699606 0.948068 0.041 Uiso 1 1 calc R U . . .
C17 C 0.4729(3) 0.80979(12) 0.89638(13) 0.0361(5) Uani 1 1 d . . . . .
C18 C 0.3202(3) 0.85159(12) 0.84994(14) 0.0402(5) Uani 1 1 d . . . . .
H18 H 0.336878 0.906356 0.837268 0.048 Uiso 1 1 calc R U . . .
C19 C 0.1428(3) 0.81305(13) 0.82208(15) 0.0417(5) Uani 1 1 d . . . . .
H19 H 0.041612 0.841949 0.791037 0.050 Uiso 1 1 calc R U . . .
C20 C 0.1165(3) 0.73116(12) 0.84059(14) 0.0379(5) Uani 1 1 d . . . . .
H20 H -0.001649 0.705065 0.821145 0.045 Uiso 1 1 calc R U . . .
C21 C 0.6674(4) 0.85136(15) 0.92359(18) 0.0533(6) Uani 1 1 d . . . . .
H21A H 0.760896 0.812104 0.948846 0.080 Uiso 1 1 calc R U . . .
H21B H 0.646973 0.893107 0.964283 0.080 Uiso 1 1 calc R U . . .
H21C H 0.718529 0.875409 0.875013 0.080 Uiso 1 1 calc R U . . .
B1 B 0.6539(4) 0.54065(17) 0.85853(18) 0.0413(6) Uani 1 1 d . . . . .
H1A H 0.692(4) 0.6009(16) 0.8373(17) 0.050(7) Uiso 1 1 d . . . . .
H1B H 0.714(4) 0.4957(17) 0.8182(19) 0.060(8) Uiso 1 1 d . . . . .
H1C H 0.691(4) 0.5263(17) 0.927(2) 0.063(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.815(2) . ?
P1 C8 1.8170(19) . ?
P1 C14 1.8323(18) . ?
P1 B1 1.923(3) . ?
C1 C2 1.388(3) . ?
C1 C6 1.395(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9300 . ?
C8 C9 1.386(3) . ?
C8 C13 1.383(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.390(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.366(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.365(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(4) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.513(3) . ?
C15 C16 1.392(3) . ?
C15 C20 1.386(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.394(3) . ?
C17 C18 1.386(3) . ?
C17 C21 1.504(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
B1 H1A 1.08(3) . ?
B1 H1B 1.08(3) . ?
B1 H1C 1.11(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
C1 P1 C8 104.34(9) . . ?
C1 P1 C14 106.02(9) . . ?
C1 P1 B1 112.48(11) . . ?
C8 P1 C14 106.74(9) . . ?
C8 P1 B1 111.90(11) . . ?
C14 P1 B1 114.62(11) . . ?
C2 C1 P1 119.61(16) . . ?
C2 C1 C6 118.93(19) . . ?
C6 C1 P1 121.45(15) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.7(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.08(19) . . ?
C5 C6 H6 120.0 . . ?
C9 C8 P1 123.92(15) . . ?
C9 C8 C13 119.1(2) . . ?
C13 C8 P1 116.82(16) . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 119.9(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
P1 C14 H14A 109.1 . . ?
P1 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 P1 112.40(13) . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C16 C15 C14 121.16(18) . . ?
C20 C15 C14 119.61(18) . . ?
C20 C15 C16 119.23(18) . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.37(19) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 C21 121.1(2) . . ?
C18 C17 C16 118.3(2) . . ?
C18 C17 C21 120.6(2) . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 121.04(19) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 120.1(2) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
P1 B1 H1A 107.2(13) . . ?
P1 B1 H1B 107.3(15) . . ?
P1 B1 H1C 104.3(16) . . ?
H1A B1 H1B 109(2) . . ?
H1A B1 H1C 117(2) . . ?
H1B B1 H1C 112(2) . . ?

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
P1 C1 C2 C3 179.97(18) . . . . ?
P1 C1 C6 C5 -179.15(15) . . . . ?
P1 C8 C9 C10 175.47(17) . . . . ?
P1 C8 C13 C12 -175.2(2) . . . . ?
P1 C14 C15 C16 -76.3(2) . . . . ?
P1 C14 C15 C20 103.17(19) . . . . ?
C1 P1 C8 C9 -96.60(19) . . . . ?
C1 P1 C8 C13 78.74(19) . . . . ?
C1 P1 C14 C15 -60.12(16) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C8 P1 C1 C2 -133.23(17) . . . . ?
C8 P1 C1 C6 45.81(18) . . . . ?
C8 P1 C14 C15 -170.94(14) . . . . ?
C8 C9 C10 C11 -0.9(4) . . . . ?
C9 C8 C13 C12 0.4(4) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C10 C11 C12 C13 -0.4(5) . . . . ?
C11 C12 C13 C8 -0.3(5) . . . . ?
C13 C8 C9 C10 0.2(3) . . . . ?
C14 P1 C1 C2 114.27(17) . . . . ?
C14 P1 C1 C6 -66.69(17) . . . . ?
C14 P1 C8 C9 15.4(2) . . . . ?
C14 P1 C8 C13 -169.28(18) . . . . ?
C14 C15 C16 C17 178.83(17) . . . . ?
C14 C15 C20 C19 179.90(18) . . . . ?
C15 C16 C17 C18 1.5(3) . . . . ?
C15 C16 C17 C21 -177.4(2) . . . . ?
C16 C15 C20 C19 -0.7(3) . . . . ?
C16 C17 C18 C19 -1.1(3) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C18 C19 C20 C15 1.0(3) . . . . ?
C20 C15 C16 C17 -0.6(3) . . . . ?
C21 C17 C18 C19 177.8(2) . . . . ?
B1 P1 C1 C2 -11.7(2) . . . . ?
B1 P1 C1 C6 167.30(16) . . . . ?
B1 P1 C8 C9 141.51(19) . . . . ?
B1 P1 C8 C13 -43.1(2) . . . . ?
B1 P1 C14 C15 64.58(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
;
_oxdiff_exptl_absorpt_empirical_full_max 3.121
_oxdiff_exptl_absorpt_empirical_full_min 0.337
####################################################################### 
# 
# 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_20230510-sw-13
_database_code_depnum_ccdc_archive 'CCDC 2269473'
loop_
_audit_author_name
_audit_author_address
'Lin Guo'
;Harbin Institute of Technology (Shenzhen)
China
;
_audit_update_record             
;
2023-06-13 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_audit_creation_date             2023-06-09
_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         'C19 H24 B P'
_chemical_formula_sum            'C19 H24 B P'
_chemical_formula_weight         294.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H P 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'
P P 0.2955 0.4335 '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                   6.60160(10)
_cell_length_b                   17.7257(4)
_cell_length_c                   14.5686(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.613(2)
_cell_angle_gamma                90
_cell_volume                     1669.89(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8047
_cell_measurement_temperature    180.3(7)
_cell_measurement_theta_max      76.2170
_cell_measurement_theta_min      2.4520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.352
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11292
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.508
_diffrn_reflns_theta_min         3.977
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.3(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  60.00   0.50    0.05    --   46.97-121.00 117.00   50
  2  ω     77.00 110.00   0.50    0.10    --  107.00-121.00 117.00   66
  3  ω     71.00  96.00   0.50    0.05    --   46.97-151.00 -43.00   50
  4  ω     43.00 106.00   0.50    0.10    --  107.00 -94.00-120.00  126
  5  ω    102.00 128.00   0.50    0.10    --  107.00-151.00 -43.00   52
  6  ω     35.00 102.00   0.50    0.10    --  107.00 -94.00 120.00  134
  7  ω   -119.00 -32.00   0.50    0.05    --  -46.97 -57.00  30.00  174
  8  ω   -112.00 -87.00   0.50    0.05    --  -46.97-151.00 -43.00   50
  9  ω   -137.00 -88.00   0.50    0.10    --  -95.00-121.00 117.00   98
 10  ω   -113.00 -71.00   0.50    0.10    --  -95.00  15.00  90.00   84
 11  ω    -64.00 -20.00   0.50    0.10    --  -95.00  15.00  90.00   88
 12  ω   -111.00 -24.00   0.50    0.10    --  -95.00  61.00  30.00  174
 13  ω   -127.00 -28.00   0.50    0.10    --  -95.00 151.00   0.00  198
 14  ω   -110.00 -21.00   0.50    0.10    --  -95.00  30.00-120.00  178
 15  ω     95.00 143.00   0.50    0.10    --  107.00  30.00 -60.00   96
 16  ω     71.00 118.00   0.50    0.05    --   46.97 151.00   0.00   94
 17  ω    112.00 138.00   0.50    0.10    --  107.00 151.00   0.00   52
 18  ω     86.00 117.00   0.50    0.05    --   46.97  57.00  60.00   62
 19  ω     32.00  71.00   0.50    0.05    --   46.97  57.00  60.00   78
;
_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      0.0881548000
_diffrn_orient_matrix_UB_12      -0.0805340000
_diffrn_orient_matrix_UB_13      0.0002350000
_diffrn_orient_matrix_UB_21      0.2206893000
_diffrn_orient_matrix_UB_22      0.0315110000
_diffrn_orient_matrix_UB_23      0.0306578000
_diffrn_orient_matrix_UB_31      -0.0157060000
_diffrn_orient_matrix_UB_32      -0.0091290000
_diffrn_orient_matrix_UB_33      0.1034729000
_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                3056
_reflns_number_total             3261
_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 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.975
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0625
_refine_ls_restrained_S_all      1.094
_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)+(0.0790P)²+2.1350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1659
_refine_ls_wR_factor_ref         0.1725
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 C1, C6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C6 \\sim C1: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C6(H6)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B)
4.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_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
P1 P 0.53500(9) 0.79197(4) 0.31899(4) 0.0277(2) Uani 1 1 d . . . . .
C1 C 0.7417(4) 0.82956(15) 0.40927(16) 0.0306(5) Uani 1 1 d . U . . .
H1 H 0.875125 0.816491 0.393834 0.037 Uiso 1 1 calc R U . . .
C2 C 0.7319(5) 0.91654(17) 0.4229(2) 0.0477(7) Uani 1 1 d . . . . .
H2A H 0.842910 0.941568 0.400222 0.057 Uiso 1 1 calc R U . . .
H2B H 0.600654 0.936619 0.389863 0.057 Uiso 1 1 calc R U . . .
C3 C 0.7553(6) 0.9269(2) 0.5266(2) 0.0551(8) Uani 1 1 d . . . . .
H3 H 0.721880 0.977625 0.545923 0.066 Uiso 1 1 calc R U . . .
C4 C 0.9668(5) 0.8969(2) 0.5762(2) 0.0515(8) Uani 1 1 d . . . . .
H4A H 1.075167 0.915132 0.545677 0.062 Uiso 1 1 calc R U . . .
H4B H 0.997820 0.912540 0.641298 0.062 Uiso 1 1 calc R U . . .
C5 C 0.9480(6) 0.8124(2) 0.5685(2) 0.0559(8) Uani 1 1 d . . . . .
H5A H 0.959072 0.789700 0.629853 0.067 Uiso 1 1 calc R U . . .
H5B H 1.054781 0.791601 0.538964 0.067 Uiso 1 1 calc R U . . .
C6 C 0.7351(5) 0.79888(17) 0.50840(19) 0.0417(6) Uani 1 1 d . U . . .
H6 H 0.678690 0.747953 0.510900 0.050 Uiso 1 1 calc R U . . .
C7 C 0.6101(5) 0.8653(2) 0.5462(2) 0.0519(8) Uani 1 1 d . . . . .
H7A H 0.470667 0.870998 0.509890 0.062 Uiso 1 1 calc R U . . .
H7B H 0.607684 0.860384 0.612252 0.062 Uiso 1 1 calc R U . . .
C8 C 0.5629(4) 0.83663(14) 0.20926(16) 0.0312(5) Uani 1 1 d . . . . .
C9 C 0.3914(5) 0.84038(17) 0.13616(19) 0.0426(7) Uani 1 1 d . . . . .
H9 H 0.266332 0.819534 0.143488 0.051 Uiso 1 1 calc R U . . .
C10 C 0.4061(6) 0.87523(19) 0.0520(2) 0.0525(8) Uani 1 1 d . . . . .
H10 H 0.290546 0.877610 0.003504 0.063 Uiso 1 1 calc R U . . .
C11 C 0.5902(6) 0.90613(17) 0.0400(2) 0.0497(8) Uani 1 1 d . . . . .
H11 H 0.599067 0.929412 -0.016254 0.060 Uiso 1 1 calc R U . . .
C12 C 0.7617(5) 0.90240(17) 0.1120(2) 0.0460(7) Uani 1 1 d . . . . .
H12 H 0.886611 0.923049 0.104114 0.055 Uiso 1 1 calc R U . . .
C13 C 0.7478(4) 0.86764(16) 0.19650(19) 0.0371(6) Uani 1 1 d . . . . .
H13 H 0.863797 0.865295 0.244702 0.045 Uiso 1 1 calc R U . . .
B B 0.2598(5) 0.8049(2) 0.3406(2) 0.0405(7) Uani 1 1 d . . . . .
C15 C 0.5964(4) 0.69249(14) 0.30882(16) 0.0300(5) Uani 1 1 d . . . . .
C16 C 0.7993(4) 0.66582(15) 0.32681(19) 0.0366(6) Uani 1 1 d . . . . .
H16 H 0.908522 0.699264 0.345145 0.044 Uiso 1 1 calc R U . . .
C17 C 0.8390(5) 0.58973(17) 0.3175(2) 0.0446(7) Uani 1 1 d . . . . .
H17 H 0.974676 0.572351 0.329827 0.053 Uiso 1 1 calc R U . . .
C18 C 0.6782(6) 0.53957(16) 0.2899(2) 0.0468(7) Uani 1 1 d . . . . .
H18 H 0.705479 0.488614 0.283259 0.056 Uiso 1 1 calc R U . . .
C19 C 0.4768(5) 0.56534(17) 0.2724(2) 0.0465(7) Uani 1 1 d . . . . .
H19 H 0.368235 0.531653 0.254057 0.056 Uiso 1 1 calc R U . . .
C20 C 0.4362(5) 0.64127(16) 0.28195(18) 0.0387(6) Uani 1 1 d . . . . .
H20 H 0.300000 0.658152 0.270259 0.046 Uiso 1 1 calc R U . . .
HA H 0.251(5) 0.7753(19) 0.405(2) 0.046(9) Uiso 1 1 d . . . . .
HB H 0.154(5) 0.777(2) 0.279(3) 0.052(9) Uiso 1 1 d . . . . .
HC H 0.228(6) 0.869(2) 0.344(3) 0.059(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.820(3) . ?
P1 C8 1.826(3) . ?
P1 B 1.919(3) . ?
P1 C15 1.822(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.558(4) . ?
C1 C6 1.552(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.498(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.533(5) . ?
C3 C7 1.518(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.505(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.518(4) . ?
C6 H6 0.9800 . ?
C6 C7 1.598(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.391(4) . ?
C8 C13 1.385(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.394(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.397(4) . ?
C13 H13 0.9300 . ?
B HA 1.09(3) . ?
B HB 1.13(4) . ?
B HC 1.16(4) . ?
C15 C16 1.395(4) . ?
C15 C20 1.389(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.380(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(4) . ?
C20 H20 0.9300 . ?

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 P1 C8 106.32(12) . . ?
C1 P1 B 115.74(13) . . ?
C1 P1 C15 105.45(12) . . ?
C8 P1 B 110.94(14) . . ?
C15 P1 C8 106.57(11) . . ?
C15 P1 B 111.25(14) . . ?
P1 C1 H1 109.0 . . ?
C2 C1 P1 114.22(19) . . ?
C2 C1 H1 109.0 . . ?
C6 C1 P1 112.77(18) . . ?
C6 C1 H1 109.0 . . ?
C6 C1 C2 102.6(2) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 C1 104.6(3) . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C2 C3 H3 114.8 . . ?
C2 C3 C4 109.4(3) . . ?
C2 C3 C7 99.2(3) . . ?
C4 C3 H3 114.8 . . ?
C7 C3 H3 114.8 . . ?
C7 C3 C4 102.2(3) . . ?
C3 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C5 C4 C3 104.9(3) . . ?
C5 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
C4 C5 H5A 110.8 . . ?
C4 C5 H5B 110.8 . . ?
C4 C5 C6 104.7(3) . . ?
H5A C5 H5B 108.9 . . ?
C6 C5 H5A 110.8 . . ?
C6 C5 H5B 110.8 . . ?
C1 C6 H6 116.1 . . ?
C1 C6 C7 100.1(2) . . ?
C5 C6 C1 106.6(2) . . ?
C5 C6 H6 116.1 . . ?
C5 C6 C7 99.6(3) . . ?
C7 C6 H6 116.1 . . ?
C3 C7 C6 94.4(2) . . ?
C3 C7 H7A 112.9 . . ?
C3 C7 H7B 112.9 . . ?
C6 C7 H7A 112.9 . . ?
C6 C7 H7B 112.9 . . ?
H7A C7 H7B 110.3 . . ?
C9 C8 P1 118.7(2) . . ?
C13 C8 P1 122.44(19) . . ?
C13 C8 C9 118.8(2) . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.7(3) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 120.6(3) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
P1 B HA 107.4(17) . . ?
P1 B HB 105.5(18) . . ?
P1 B HC 108.0(19) . . ?
HA B HB 111(3) . . ?
HA B HC 113(3) . . ?
HB B HC 112(3) . . ?
C16 C15 P1 122.25(19) . . ?
C20 C15 P1 119.1(2) . . ?
C20 C15 C16 118.6(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.1(3) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.8(3) . . ?
C19 C20 H20 119.6 . . ?

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
P1 C1 C2 C3 131.1(2) . . . . ?
P1 C1 C6 C5 161.2(2) . . . . ?
P1 C1 C6 C7 -95.5(2) . . . . ?
P1 C8 C9 C10 178.9(2) . . . . ?
P1 C8 C13 C12 -178.9(2) . . . . ?
P1 C15 C16 C17 -179.5(2) . . . . ?
P1 C15 C20 C19 179.2(2) . . . . ?
C1 P1 C8 C9 -157.4(2) . . . . ?
C1 P1 C8 C13 21.9(3) . . . . ?
C1 P1 C15 C16 -30.0(2) . . . . ?
C1 P1 C15 C20 150.2(2) . . . . ?
C1 C2 C3 C4 62.3(3) . . . . ?
C1 C2 C3 C7 -44.2(3) . . . . ?
C1 C6 C7 C3 -54.0(3) . . . . ?
C2 C1 C6 C5 -75.4(3) . . . . ?
C2 C1 C6 C7 27.9(3) . . . . ?
C2 C3 C4 C5 -72.6(3) . . . . ?
C2 C3 C7 C6 59.8(3) . . . . ?
C3 C4 C5 C6 4.6(3) . . . . ?
C4 C3 C7 C6 -52.4(3) . . . . ?
C4 C5 C6 C1 66.5(3) . . . . ?
C4 C5 C6 C7 -37.1(3) . . . . ?
C5 C6 C7 C3 54.9(3) . . . . ?
C6 C1 C2 C3 8.7(3) . . . . ?
C7 C3 C4 C5 31.8(3) . . . . ?
C8 P1 C1 C2 61.4(2) . . . . ?
C8 P1 C1 C6 178.08(19) . . . . ?
C8 P1 C15 C16 82.7(2) . . . . ?
C8 P1 C15 C20 -97.1(2) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
C9 C8 C13 C12 0.3(4) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?
C11 C12 C13 C8 0.0(4) . . . . ?
C13 C8 C9 C10 -0.4(4) . . . . ?
B P1 C1 C2 -62.3(2) . . . . ?
B P1 C1 C6 54.4(3) . . . . ?
B P1 C8 C9 -30.8(3) . . . . ?
B P1 C8 C13 148.5(2) . . . . ?
B P1 C15 C16 -156.3(2) . . . . ?
B P1 C15 C20 24.0(2) . . . . ?
C15 P1 C1 C2 174.3(2) . . . . ?
C15 P1 C1 C6 -69.0(2) . . . . ?
C15 P1 C8 C9 90.5(2) . . . . ?
C15 P1 C8 C13 -90.3(2) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C16 C15 C20 C19 -0.6(4) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C20 0.3(4) . . . . ?
C18 C19 C20 C15 0.3(4) . . . . ?
C20 C15 C16 C17 0.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.181
_oxdiff_exptl_absorpt_empirical_full_min 0.486
