# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_ak-cis0809
_database_code_depnum_ccdc_archive 'CCDC 1900168'
loop_
_audit_author_name
_audit_author_address
'Kiyoshi Tsuge'
;University of Toyama
Japan
;
_audit_update_record             
;
2019-02-28 deposited with the CCDC.	2019-04-30 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C30 H33 B F4 N O4 P'
_chemical_formula_moiety         'C30 H33 B F4 N O4 P'
_chemical_formula_weight         589.37
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -1/2+X,+Y,-1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   10.49949(19)
_cell_length_b                   15.8323(3)
_cell_length_c                   35.2366(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     5857.41(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    39997
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      68.20
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2464.00
_exptl_absorpt_coefficient_mu    1.370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.680
_exptl_absorpt_correction_T_max  0.973

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            63297
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_theta_max         68.223
_diffrn_reflns_theta_min         4.903
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       42
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5355
_reflns_number_gt                3870
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.2004
_refine_ls_wR_factor_gt          0.1841
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5355
_refine_ls_number_parameters     391
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1027P)²+5.2183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.09
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.2955 0.4335
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.64588(9) 0.60383(6) 0.67841(2) 0.0377(3) Uani 1 1 d . . . . .
F1 F 0.4418(3) 1.00315(18) 0.60705(8) 0.0864(9) Uani 1 1 d . . . . .
F2 F 0.2916(3) 1.00334(18) 0.56194(9) 0.0917(10) Uani 1 1 d . . . . .
F3 F 0.4574(11) 0.9260(8) 0.5536(3) 0.135(4) Uani 0.5 1 d . . P . .
F4 F 0.3195(16) 0.8910(7) 0.5971(4) 0.180(6) Uani 0.5 1 d . . P . .
F5 F 0.4078(9) 0.8839(6) 0.5735(6) 0.153(7) Uani 0.5 1 d . . P . .
F6 F 0.2558(7) 0.9325(5) 0.61290(18) 0.0828(19) Uani 0.5 1 d . . P . .
O1 O 0.6672(2) 0.53002(14) 0.65292(6) 0.0421(6) Uani 1 1 d . . . . .
O2 O 0.2617(2) 0.67388(16) 0.50066(6) 0.0442(6) Uani 1 1 d . . . . .
O3 O 0.4018(2) 0.59057(15) 0.45352(6) 0.0431(6) Uani 1 1 d . . . . .
O4 O 0.8559(3) 0.41665(17) 0.64211(8) 0.0594(8) Uani 1 1 d . . . . .
N1 N 0.6543(3) 0.81910(17) 0.57733(8) 0.0419(7) Uani 1 1 d . . . . .
H1A H 0.582859 0.844782 0.568375 0.050 Uiso 1 1 calc R U . . .
H1B H 0.717124 0.822427 0.559596 0.050 Uiso 1 1 calc R U . . .
H1C H 0.680200 0.845306 0.598989 0.050 Uiso 1 1 calc R U . . .
C1 C 0.6258(3) 0.7275(2) 0.58570(9) 0.0367(8) Uani 1 1 d . . . . .
H1 H 0.559909 0.725325 0.606158 0.044 Uiso 1 1 calc R U . . .
C2 C 0.7458(3) 0.6803(2) 0.59998(9) 0.0393(8) Uani 1 1 d . . . . .
H2 H 0.716924 0.621883 0.606449 0.047 Uiso 1 1 calc R U . . .
C3 C 0.8414(3) 0.6704(2) 0.56742(10) 0.0435(9) Uani 1 1 d . . . . .
H3A H 0.919889 0.642971 0.576919 0.052 Uiso 1 1 calc R U . . .
H3B H 0.864525 0.726719 0.557335 0.052 Uiso 1 1 calc R U . . .
C4 C 0.7826(3) 0.6166(2) 0.53570(10) 0.0432(9) Uani 1 1 d . . . . .
H4A H 0.833362 0.624485 0.512287 0.052 Uiso 1 1 calc R U . . .
H4B H 0.788779 0.556319 0.542974 0.052 Uiso 1 1 calc R U . . .
C5 C 0.6450(3) 0.6369(2) 0.52708(9) 0.0374(8) Uani 1 1 d . . . . .
C6 C 0.5894(3) 0.6033(2) 0.49419(9) 0.0361(8) Uani 1 1 d . . . . .
H6 H 0.639559 0.569936 0.477509 0.043 Uiso 1 1 calc R U . . .
C7 C 0.4633(3) 0.6178(2) 0.48567(9) 0.0365(8) Uani 1 1 d . . . . .
C8 C 0.3880(3) 0.6647(2) 0.51076(10) 0.0373(8) Uani 1 1 d . . . . .
C9 C 0.4410(3) 0.6985(2) 0.54303(9) 0.0383(8) Uani 1 1 d . . . . .
H9 H 0.389895 0.730344 0.560065 0.046 Uiso 1 1 calc R U . . .
C10 C 0.5716(3) 0.6859(2) 0.55082(9) 0.0364(8) Uani 1 1 d . . . . .
C11 C 0.7996(3) 0.7170(2) 0.63642(10) 0.0401(8) Uani 1 1 d . . . . .
C12 C 0.7615(3) 0.6887(2) 0.67256(9) 0.0379(8) Uani 1 1 d . . . . .
C13 C 0.8094(4) 0.7284(2) 0.70481(10) 0.0450(9) Uani 1 1 d . . . . .
H13 H 0.783754 0.709102 0.729164 0.054 Uiso 1 1 calc R U . . .
C14 C 0.8936(4) 0.7953(2) 0.70210(11) 0.0485(9) Uani 1 1 d . . . . .
H14 H 0.923790 0.822495 0.724385 0.058 Uiso 1 1 calc R U . . .
C15 C 0.9332(4) 0.8219(2) 0.66716(11) 0.0505(10) Uani 1 1 d . . . . .
H15 H 0.992073 0.867198 0.665061 0.061 Uiso 1 1 calc R U . . .
C16 C 0.8870(4) 0.7825(2) 0.63468(11) 0.0475(9) Uani 1 1 d . . . . .
H16 H 0.916281 0.801051 0.610568 0.057 Uiso 1 1 calc R U . . .
C17 C 0.6520(4) 0.5702(2) 0.72730(10) 0.0433(8) Uani 1 1 d . . . . .
C18 C 0.7397(5) 0.5090(3) 0.73674(11) 0.0572(11) Uani 1 1 d . . . . .
H18 H 0.795931 0.487590 0.717921 0.069 Uiso 1 1 calc R U . . .
C19 C 0.7465(5) 0.4784(3) 0.77353(12) 0.0684(13) Uani 1 1 d . . . . .
H19 H 0.807781 0.436675 0.779962 0.082 Uiso 1 1 calc R U . . .
C20 C 0.6648(5) 0.5084(3) 0.80057(12) 0.0674(13) Uani 1 1 d . . . . .
H20 H 0.669098 0.487133 0.825738 0.081 Uiso 1 1 calc R U . . .
C21 C 0.5769(5) 0.5690(3) 0.79159(11) 0.0705(13) Uani 1 1 d . . . . .
H21 H 0.520130 0.589380 0.810465 0.085 Uiso 1 1 calc R U . . .
C22 C 0.5708(4) 0.6005(3) 0.75502(11) 0.0610(11) Uani 1 1 d . . . . .
H22 H 0.510501 0.643105 0.748927 0.073 Uiso 1 1 calc R U . . .
C23 C 0.4950(4) 0.6533(2) 0.66949(9) 0.0393(8) Uani 1 1 d . . . . .
C24 C 0.4676(4) 0.7353(3) 0.68102(11) 0.0535(10) Uani 1 1 d . . . . .
H24 H 0.527852 0.765807 0.695737 0.064 Uiso 1 1 calc R U . . .
C25 C 0.3537(5) 0.7727(3) 0.67126(14) 0.0680(13) Uani 1 1 d . . . . .
H25 H 0.335661 0.828648 0.679348 0.082 Uiso 1 1 calc R U . . .
C26 C 0.2659(4) 0.7289(3) 0.64977(14) 0.0676(12) Uani 1 1 d . . . . .
H26 H 0.187559 0.755040 0.643105 0.081 Uiso 1 1 calc R U . . .
C27 C 0.2908(4) 0.6483(3) 0.63799(12) 0.0573(11) Uani 1 1 d . . . . .
H27 H 0.230325 0.618737 0.622953 0.069 Uiso 1 1 calc R U . . .
C28 C 0.4055(4) 0.6093(2) 0.64811(10) 0.0452(9) Uani 1 1 d . . . . .
H28 H 0.422307 0.552876 0.640405 0.054 Uiso 1 1 calc R U . . .
C29 C 0.1743(4) 0.6951(3) 0.53012(11) 0.0529(10) Uani 1 1 d . . . . .
H29A H 0.087570 0.696276 0.519829 0.063 Uiso 1 1 calc R U . . .
H29B H 0.195715 0.750858 0.540393 0.063 Uiso 1 1 calc R U . . .
H29C H 0.179422 0.652840 0.550370 0.063 Uiso 1 1 calc R U . . .
C30 C 0.4764(4) 0.5418(2) 0.42702(9) 0.0450(9) Uani 1 1 d . . . . .
H30A H 0.422933 0.525169 0.405496 0.054 Uiso 1 1 calc R U . . .
H30B H 0.509095 0.491119 0.439694 0.054 Uiso 1 1 calc R U . . .
H30C H 0.547990 0.575950 0.417887 0.054 Uiso 1 1 calc R U . . .
B1 B 0.3624(6) 0.9563(4) 0.58450(19) 0.0721(17) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O1 1.491(2) . ?
P1 C23 1.795(4) . ?
P1 C17 1.804(4) . ?
P1 C12 1.823(4) . ?
F1 B1 1.370(6) . ?
F2 B1 1.319(6) . ?
F3 F5 1.097(16) . ?
F3 B1 1.552(12) . ?
F4 F6 1.090(15) . ?
F4 B1 1.213(11) . ?
F4 F5 1.252(17) . ?
F5 B1 1.300(10) . ?
F6 B1 1.548(10) . ?
O2 C8 1.380(4) . ?
O2 C29 1.426(4) . ?
O3 C7 1.373(4) . ?
O3 C30 1.443(4) . ?
N1 C1 1.509(4) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C1 C10 1.506(4) . ?
C1 C2 1.549(5) . ?
C1 H1 1.0000 . ?
C2 C11 1.519(5) . ?
C2 C3 1.533(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.535(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.511(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.376(5) . ?
C5 C6 1.403(4) . ?
C6 C7 1.377(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.399(5) . ?
C8 C9 1.375(5) . ?
C9 C10 1.413(5) . ?
C9 H9 0.9500 . ?
C11 C16 1.386(5) . ?
C11 C12 1.408(5) . ?
C12 C13 1.392(5) . ?
C13 C14 1.383(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.366(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.377(5) . ?
C17 C22 1.383(5) . ?
C18 C19 1.385(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.367(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.367(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.383(6) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.390(5) . ?
C23 C28 1.391(5) . ?
C24 C25 1.377(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.369(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.400(5) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C23 111.69(15) . . ?
O1 P1 C17 109.77(15) . . ?
C23 P1 C17 109.13(17) . . ?
O1 P1 C12 114.17(15) . . ?
C23 P1 C12 104.25(16) . . ?
C17 P1 C12 107.57(16) . . ?
F5 F3 B1 55.7(8) . . ?
F6 F4 B1 84.3(10) . . ?
F6 F4 F5 147.9(13) . . ?
B1 F4 F5 63.7(8) . . ?
F3 F5 F4 136.2(13) . . ?
F3 F5 B1 80.2(10) . . ?
F4 F5 B1 56.7(7) . . ?
F4 F6 B1 51.2(7) . . ?
C8 O2 C29 117.1(3) . . ?
C7 O3 C30 116.5(3) . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C10 C1 N1 109.6(3) . . ?
C10 C1 C2 111.2(3) . . ?
N1 C1 C2 111.5(3) . . ?
C10 C1 H1 108.2 . . ?
N1 C1 H1 108.2 . . ?
C2 C1 H1 108.2 . . ?
C11 C2 C3 115.4(3) . . ?
C11 C2 C1 113.1(3) . . ?
C3 C2 C1 109.8(3) . . ?
C11 C2 H2 105.9 . . ?
C3 C2 H2 105.9 . . ?
C1 C2 H2 105.9 . . ?
C2 C3 C4 109.8(3) . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 114.3(3) . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C10 C5 C6 118.9(3) . . ?
C10 C5 C4 122.2(3) . . ?
C6 C5 C4 118.9(3) . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O3 C7 C6 125.4(3) . . ?
O3 C7 C8 115.0(3) . . ?
C6 C7 C8 119.6(3) . . ?
C9 C8 O2 124.1(3) . . ?
C9 C8 C7 120.0(3) . . ?
O2 C8 C7 115.8(3) . . ?
C8 C9 C10 119.9(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C10 C9 120.3(3) . . ?
C5 C10 C1 122.1(3) . . ?
C9 C10 C1 117.6(3) . . ?
C16 C11 C12 117.8(3) . . ?
C16 C11 C2 119.7(3) . . ?
C12 C11 C2 122.5(3) . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 P1 118.7(3) . . ?
C11 C12 P1 121.8(3) . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 119.5(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 119.8(4) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 122.0(4) . . ?
C11 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C18 C17 C22 119.1(4) . . ?
C18 C17 P1 117.6(3) . . ?
C22 C17 P1 123.3(3) . . ?
C17 C18 C19 120.4(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 119.9(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.4(4) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C22 120.0(4) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 120.3(4) . . ?
C17 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C28 119.1(4) . . ?
C24 C23 P1 122.6(3) . . ?
C28 C23 P1 118.1(3) . . ?
C25 C24 C23 120.5(4) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 120.1(4) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 120.5(4) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 119.9(4) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C23 C28 C27 119.9(4) . . ?
C23 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
O2 C29 H29A 109.5 . . ?
O2 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O2 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O3 C30 H30A 109.5 . . ?
O3 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O3 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
F4 B1 F5 59.6(8) . . ?
F4 B1 F2 119.6(9) . . ?
F5 B1 F2 121.6(9) . . ?
F4 B1 F1 118.3(8) . . ?
F5 B1 F1 115.3(6) . . ?
F2 B1 F1 112.7(5) . . ?
F4 B1 F6 44.5(8) . . ?
F5 B1 F6 104.2(10) . . ?
F2 B1 F6 96.9(5) . . ?
F1 B1 F6 101.4(5) . . ?
F4 B1 F3 103.4(9) . . ?
F5 B1 F3 44.1(7) . . ?
F2 B1 F3 96.6(6) . . ?
F1 B1 F3 100.5(6) . . ?
F6 B1 F3 147.4(7) . . ?

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
B1 F3 F5 F4 9.7(19) . . . . ?
F6 F4 F5 F3 -10(5) . . . . ?
B1 F4 F5 F3 -11(2) . . . . ?
F6 F4 F5 B1 2(3) . . . . ?
F5 F4 F6 B1 -2(2) . . . . ?
C10 C1 C2 C11 -176.8(3) . . . . ?
N1 C1 C2 C11 60.6(4) . . . . ?
C10 C1 C2 C3 52.8(4) . . . . ?
N1 C1 C2 C3 -69.9(3) . . . . ?
C11 C2 C3 C4 168.4(3) . . . . ?
C1 C2 C3 C4 -62.4(4) . . . . ?
C2 C3 C4 C5 42.0(4) . . . . ?
C3 C4 C5 C10 -13.3(5) . . . . ?
C3 C4 C5 C6 168.1(3) . . . . ?
C10 C5 C6 C7 -0.7(5) . . . . ?
C4 C5 C6 C7 178.0(3) . . . . ?
C30 O3 C7 C6 1.0(5) . . . . ?
C30 O3 C7 C8 -179.8(3) . . . . ?
C5 C6 C7 O3 177.2(3) . . . . ?
C5 C6 C7 C8 -2.0(5) . . . . ?
C29 O2 C8 C9 -20.8(5) . . . . ?
C29 O2 C8 C7 159.5(3) . . . . ?
O3 C7 C8 C9 -176.9(3) . . . . ?
C6 C7 C8 C9 2.3(5) . . . . ?
O3 C7 C8 O2 2.8(4) . . . . ?
C6 C7 C8 O2 -178.0(3) . . . . ?
O2 C8 C9 C10 -179.7(3) . . . . ?
C7 C8 C9 C10 0.0(5) . . . . ?
C6 C5 C10 C9 3.1(5) . . . . ?
C4 C5 C10 C9 -175.6(3) . . . . ?
C6 C5 C10 C1 -177.2(3) . . . . ?
C4 C5 C10 C1 4.2(5) . . . . ?
C8 C9 C10 C5 -2.7(5) . . . . ?
C8 C9 C10 C1 177.5(3) . . . . ?
N1 C1 C10 C5 99.6(4) . . . . ?
C2 C1 C10 C5 -24.0(4) . . . . ?
N1 C1 C10 C9 -80.6(4) . . . . ?
C2 C1 C10 C9 155.7(3) . . . . ?
C3 C2 C11 C16 39.9(5) . . . . ?
C1 C2 C11 C16 -87.7(4) . . . . ?
C3 C2 C11 C12 -142.0(3) . . . . ?
C1 C2 C11 C12 90.4(4) . . . . ?
C16 C11 C12 C13 1.8(5) . . . . ?
C2 C11 C12 C13 -176.4(3) . . . . ?
C16 C11 C12 P1 179.3(3) . . . . ?
C2 C11 C12 P1 1.1(5) . . . . ?
O1 P1 C12 C13 -137.9(3) . . . . ?
C23 P1 C12 C13 99.9(3) . . . . ?
C17 P1 C12 C13 -15.9(3) . . . . ?
O1 P1 C12 C11 44.5(3) . . . . ?
C23 P1 C12 C11 -77.7(3) . . . . ?
C17 P1 C12 C11 166.6(3) . . . . ?
C11 C12 C13 C14 0.1(5) . . . . ?
P1 C12 C13 C14 -177.5(3) . . . . ?
C12 C13 C14 C15 -1.5(6) . . . . ?
C13 C14 C15 C16 1.0(6) . . . . ?
C12 C11 C16 C15 -2.3(6) . . . . ?
C2 C11 C16 C15 175.9(4) . . . . ?
C14 C15 C16 C11 1.0(6) . . . . ?
O1 P1 C17 C18 37.4(4) . . . . ?
C23 P1 C17 C18 160.1(3) . . . . ?
C12 P1 C17 C18 -87.3(3) . . . . ?
O1 P1 C17 C22 -140.3(3) . . . . ?
C23 P1 C17 C22 -17.6(4) . . . . ?
C12 P1 C17 C22 95.0(4) . . . . ?
C22 C17 C18 C19 -0.1(6) . . . . ?
P1 C17 C18 C19 -177.9(4) . . . . ?
C17 C18 C19 C20 0.7(7) . . . . ?
C18 C19 C20 C21 -0.5(7) . . . . ?
C19 C20 C21 C22 -0.3(7) . . . . ?
C18 C17 C22 C21 -0.7(6) . . . . ?
P1 C17 C22 C21 177.0(4) . . . . ?
C20 C21 C22 C17 0.9(7) . . . . ?
O1 P1 C23 C24 -161.0(3) . . . . ?
C17 P1 C23 C24 77.5(3) . . . . ?
C12 P1 C23 C24 -37.2(3) . . . . ?
O1 P1 C23 C28 14.9(3) . . . . ?
C17 P1 C23 C28 -106.6(3) . . . . ?
C12 P1 C23 C28 138.7(3) . . . . ?
C28 C23 C24 C25 -0.3(6) . . . . ?
P1 C23 C24 C25 175.5(3) . . . . ?
C23 C24 C25 C26 -0.2(7) . . . . ?
C24 C25 C26 C27 0.1(7) . . . . ?
C25 C26 C27 C28 0.7(7) . . . . ?
C24 C23 C28 C27 1.1(5) . . . . ?
P1 C23 C28 C27 -174.9(3) . . . . ?
C26 C27 C28 C23 -1.3(6) . . . . ?
F6 F4 B1 F5 -179.0(14) . . . . ?
F6 F4 B1 F2 -67.5(11) . . . . ?
F5 F4 B1 F2 111.5(12) . . . . ?
F6 F4 B1 F1 76.7(11) . . . . ?
F5 F4 B1 F1 -104.3(9) . . . . ?
F5 F4 B1 F6 179.0(14) . . . . ?
F6 F4 B1 F3 -173.3(8) . . . . ?
F5 F4 B1 F3 5.7(12) . . . . ?
F3 F5 B1 F4 172.0(16) . . . . ?
F3 F5 B1 F2 63.8(10) . . . . ?
F4 F5 B1 F2 -108.2(13) . . . . ?
F3 F5 B1 F1 -78.6(14) . . . . ?
F4 F5 B1 F1 109.4(10) . . . . ?
F3 F5 B1 F6 171.2(9) . . . . ?
F4 F5 B1 F6 -0.7(10) . . . . ?
F4 F5 B1 F3 -172.0(16) . . . . ?
F4 F6 B1 F5 0.9(13) . . . . ?
F4 F6 B1 F2 126.0(11) . . . . ?
F4 F6 B1 F1 -119.1(11) . . . . ?
F4 F6 B1 F3 12.2(14) . . . . ?
F5 F3 B1 F4 -7.1(14) . . . . ?
F5 F3 B1 F2 -129.7(11) . . . . ?
F5 F3 B1 F1 115.6(11) . . . . ?
F5 F3 B1 F6 -15.9(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A F3 . . . 2.799(12) 0.910 1.912 164.3 no
N1 H1A F5 . . . 2.787(10) 0.910 1.947 152.7 no
N1 H1B O2 . . 2_566 2.973(4) 0.910 2.175 145.9 no
N1 H1C O4 . . 6_765 2.758(4) 0.910 1.931 150.2 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_ak-trans2
_database_code_depnum_ccdc_archive 'CCDC 1900169'
loop_
_audit_author_name
_audit_author_address
'Kiyoshi Tsuge'
;University of Toyama
Japan
;
_audit_update_record             
;
2019-02-28 deposited with the CCDC.	2019-04-30 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C37 H39 B F4 N O3 P'
_chemical_formula_moiety         'C37 H39 B F4 N O3 P'
_chemical_formula_weight         663.50
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.93080(14)
_cell_length_b                   13.1455(2)
_cell_length_c                   17.4250(3)
_cell_angle_alpha                76.619(5)
_cell_angle_beta                 88.302(6)
_cell_angle_gamma                73.541(5)
_cell_volume                     1693.64(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15649
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      68.26
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696.00
_exptl_absorpt_coefficient_mu    1.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_T_max  0.929

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            19539
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_theta_max         68.231
_diffrn_reflns_theta_min         3.605
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6073
_reflns_number_gt                4610
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1644
_refine_ls_wR_factor_gt          0.1549
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6073
_refine_ls_number_parameters     454
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0935P)²+0.1158P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.2955 0.4335
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.58896(8) 0.19342(5) 0.86614(3) 0.03468(18) Uani 1 1 d . . . . .
F1 F 0.3600(2) 0.66123(14) 0.65955(11) 0.0740(5) Uani 1 1 d . . . . .
F2 F 0.1752(3) 0.62126(17) 0.75303(11) 0.1001(7) Uani 1 1 d . . . . .
F3 F 0.2419(3) 0.78168(15) 0.73358(11) 0.0910(6) Uani 1 1 d . . . . .
F4 F 0.0741(2) 0.75354(16) 0.64385(11) 0.0827(6) Uani 1 1 d . . . . .
O1 O 0.6418(2) 0.28993(13) 0.82004(8) 0.0429(4) Uani 1 1 d . . . . .
O2 O 0.2483(2) 0.64007(13) 0.41102(8) 0.0440(4) Uani 1 1 d . . . . .
O3 O 0.2293(2) 0.49000(13) 0.34125(8) 0.0468(4) Uani 1 1 d . . . . .
N1 N 0.4469(3) 0.42676(15) 0.69532(10) 0.0379(5) Uani 1 1 d . . . . .
H1A H 0.529832 0.412702 0.658980 0.045 Uiso 1 1 calc R U . . .
H1B H 0.491445 0.387191 0.744148 0.045 Uiso 1 1 calc R U . . .
H1C H 0.415876 0.499088 0.694776 0.045 Uiso 1 1 calc R U . . .
C1 C 0.2858(3) 0.39549(18) 0.67535(12) 0.0342(5) Uani 1 1 d . . . . .
H1 H 0.179637 0.445025 0.693374 0.041 Uiso 1 1 calc R U . . .
C2 C 0.3028(3) 0.27735(17) 0.72190(12) 0.0332(5) Uani 1 1 d . . . . .
H2 H 0.430032 0.235243 0.725443 0.040 Uiso 1 1 calc R U . . .
C3 C 0.2017(3) 0.22249(19) 0.67857(13) 0.0411(6) Uani 1 1 d . . . . .
H3A H 0.213462 0.147259 0.709381 0.049 Uiso 1 1 calc R U . . .
H3B H 0.075289 0.263341 0.673756 0.049 Uiso 1 1 calc R U . . .
C4 C 0.2728(4) 0.21929(19) 0.59648(13) 0.0436(6) Uani 1 1 d . . . . .
H4A H 0.396393 0.173176 0.601460 0.052 Uiso 1 1 calc R U . . .
H4B H 0.202952 0.186451 0.568475 0.052 Uiso 1 1 calc R U . . .
C5 C 0.2635(3) 0.33294(19) 0.54926(13) 0.0371(5) Uani 1 1 d . . . . .
C6 C 0.2486(3) 0.35724(19) 0.46659(13) 0.0390(6) Uani 1 1 d . . . . .
H6 H 0.242863 0.301953 0.440837 0.047 Uiso 1 1 calc R U . . .
C7 C 0.2420(3) 0.4592(2) 0.42219(12) 0.0384(6) Uani 1 1 d . . . . .
C8 C 0.2494(3) 0.54119(18) 0.45975(12) 0.0363(5) Uani 1 1 d . . . . .
C9 C 0.2601(3) 0.51905(18) 0.54117(12) 0.0359(5) Uani 1 1 d . . . . .
H9 H 0.261369 0.575333 0.566723 0.043 Uiso 1 1 calc R U . . .
C10 C 0.2692(3) 0.41463(18) 0.58646(12) 0.0338(5) Uani 1 1 d . . . . .
C11 C 0.2391(3) 0.27432(17) 0.80614(12) 0.0333(5) Uani 1 1 d . . . . .
C12 C 0.3521(3) 0.22923(17) 0.87444(12) 0.0327(5) Uani 1 1 d . . . . .
C13 C 0.2801(3) 0.22530(19) 0.94877(13) 0.0382(5) Uani 1 1 d . . . . .
H13 H 0.355778 0.194841 0.994611 0.046 Uiso 1 1 calc R U . . .
C14 C 0.1012(3) 0.2647(2) 0.95713(14) 0.0432(6) Uani 1 1 d . . . . .
H14 H 0.054155 0.260167 1.008176 0.052 Uiso 1 1 calc R U . . .
C15 C -0.0081(3) 0.31078(19) 0.89068(14) 0.0411(6) Uani 1 1 d . . . . .
H15 H -0.130869 0.340141 0.895736 0.049 Uiso 1 1 calc R U . . .
C16 C 0.0611(3) 0.31426(18) 0.81629(13) 0.0382(5) Uani 1 1 d . . . . .
H16 H -0.016285 0.345035 0.771038 0.046 Uiso 1 1 calc R U . . .
C17 C 0.6566(3) 0.0795(2) 0.82065(12) 0.0384(6) Uani 1 1 d . . . . .
C18 C 0.7889(3) 0.0773(2) 0.76581(13) 0.0495(7) Uani 1 1 d . . . . .
H18 H 0.839006 0.136389 0.751879 0.059 Uiso 1 1 calc R U . . .
C19 C 0.8468(4) -0.0112(3) 0.73186(15) 0.0622(8) Uani 1 1 d . . . . .
H19 H 0.936057 -0.012334 0.694203 0.075 Uiso 1 1 calc R U . . .
C20 C 0.7759(4) -0.0975(3) 0.75231(17) 0.0669(9) Uani 1 1 d . . . . .
H20 H 0.818559 -0.158688 0.729638 0.080 Uiso 1 1 calc R U . . .
C21 C 0.6439(4) -0.0958(3) 0.80527(18) 0.0657(8) Uani 1 1 d . . . . .
H21 H 0.593558 -0.154897 0.818369 0.079 Uiso 1 1 calc R U . . .
C22 C 0.5846(4) -0.0076(2) 0.83940(15) 0.0500(7) Uani 1 1 d . . . . .
H22 H 0.493598 -0.006549 0.876138 0.060 Uiso 1 1 calc R U . . .
C23 C 0.6831(3) 0.14750(18) 0.96499(12) 0.0342(5) Uani 1 1 d . . . . .
C24 C 0.7677(3) 0.03880(18) 0.99937(12) 0.0369(5) Uani 1 1 d . . . . .
H24 H 0.779706 -0.015136 0.969909 0.044 Uiso 1 1 calc R U . . .
C25 C 0.8347(3) 0.0089(2) 1.07681(13) 0.0431(6) Uani 1 1 d . . . . .
H25 H 0.891803 -0.065473 1.100292 0.052 Uiso 1 1 calc R U . . .
C26 C 0.8182(3) 0.0866(2) 1.11907(13) 0.0454(6) Uani 1 1 d . . . . .
H26 H 0.862987 0.065603 1.172119 0.054 Uiso 1 1 calc R U . . .
C27 C 0.7374(3) 0.1953(2) 1.08561(13) 0.0457(6) Uani 1 1 d . . . . .
H27 H 0.727940 0.248684 1.115303 0.055 Uiso 1 1 calc R U . . .
C28 C 0.6701(3) 0.2260(2) 1.00856(13) 0.0407(6) Uani 1 1 d . . . . .
H28 H 0.614895 0.300683 0.985313 0.049 Uiso 1 1 calc R U . . .
C29 C 0.2474(4) 0.7267(2) 0.44868(14) 0.0521(7) Uani 1 1 d . . . . .
H29A H 0.240422 0.793633 0.408360 0.063 Uiso 1 1 calc R U . . .
H29B H 0.355667 0.706598 0.481246 0.063 Uiso 1 1 calc R U . . .
H29C H 0.145429 0.738740 0.482107 0.063 Uiso 1 1 calc R U . . .
C30 C 0.2196(4) 0.4088(2) 0.30031(14) 0.0541(7) Uani 1 1 d . . . . .
H30A H 0.119156 0.381311 0.318419 0.065 Uiso 1 1 calc R U . . .
H30B H 0.328300 0.348484 0.311093 0.065 Uiso 1 1 calc R U . . .
H30C H 0.204757 0.441129 0.243428 0.065 Uiso 1 1 calc R U . . .
C31 C 0.4959(9) 0.5340(3) 0.9179(3) 0.1046(15) Uani 1 1 d . . . . .
C32 C 0.3541(8) 0.5053(3) 0.9549(3) 0.1026(14) Uani 1 1 d . . . . .
C33 C 0.3555(8) 0.4700(3) 1.0389(4) 0.1107(16) Uani 1 1 d . . . . .
C34 C 0.7362(8) 0.0441(4) 0.4590(3) 0.1142(16) Uani 1 1 d . . . . .
C35 C 0.5987(13) 0.0121(6) 0.4872(5) 0.079(2) Uani 0.5 1 d . . P . .
C36 C 0.7220(14) -0.0302(8) 0.5338(5) 0.097(3) Uani 0.5 1 d . . P . .
C37 C 0.5789(8) -0.0586(3) 0.5588(2) 0.0829(12) Uani 1 1 d . . . . .
C38 C 0.4431(14) -0.0871(6) 0.5842(4) 0.083(2) Uani 0.5 1 d . . P . .
C39 C 0.205(2) 0.5184(11) 0.9248(10) 0.085(5) Uani 0.25 1 d . . P . .
C40 C 0.234(2) 0.4309(10) 1.0718(7) 0.072(4) Uani 0.25 1 d . . P . .
B1 B 0.2116(5) 0.7065(3) 0.69883(19) 0.0540(8) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O1 1.4968(15) . ?
P1 C23 1.797(2) . ?
P1 C17 1.797(2) . ?
P1 C12 1.813(2) . ?
F1 B1 1.397(4) . ?
F2 B1 1.382(4) . ?
F3 B1 1.349(3) . ?
F4 B1 1.377(4) . ?
O2 C8 1.376(2) . ?
O2 C29 1.438(3) . ?
O3 C7 1.373(2) . ?
O3 C30 1.434(3) . ?
N1 C1 1.521(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C1 C10 1.514(3) . ?
C1 C2 1.547(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.532(3) . ?
C2 C11 1.534(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.527(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.512(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.388(3) . ?
C5 C6 1.402(3) . ?
C6 C7 1.371(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.400(3) . ?
C8 C9 1.381(3) . ?
C9 C10 1.399(3) . ?
C9 H9 0.9500 . ?
C11 C16 1.381(3) . ?
C11 C12 1.416(3) . ?
C12 C13 1.396(3) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.388(3) . ?
C17 C18 1.397(3) . ?
C18 C19 1.383(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.376(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.383(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.391(3) . ?
C23 C28 1.396(3) . ?
C24 C25 1.392(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.368(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.382(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.386(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.381(7) . ?
C31 C33 1.399(6) 2_667 ?
C32 C39 1.256(14) . ?
C32 C33 1.429(6) . ?
C33 C40 1.279(14) . ?
C34 C35 1.319(9) . ?
C34 C36 1.459(11) . ?
C34 C38 1.523(10) 2_656 ?
C35 C36 1.206(12) . ?
C35 C38 1.379(11) 2_656 ?
C35 C37 1.406(8) . ?
C35 C37 1.534(10) 2_656 ?
C35 C35 1.711(19) 2_656 ?
C36 C37 1.324(11) . ?
C37 C38 1.273(9) . ?

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
O1 P1 C23 112.25(10) . . ?
O1 P1 C17 111.85(10) . . ?
C23 P1 C17 107.03(11) . . ?
O1 P1 C12 109.91(10) . . ?
C23 P1 C12 106.82(10) . . ?
C17 P1 C12 108.78(11) . . ?
C8 O2 C29 116.75(16) . . ?
C7 O3 C30 116.88(18) . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C10 C1 N1 108.10(17) . . ?
C10 C1 C2 115.34(17) . . ?
N1 C1 C2 108.50(18) . . ?
C10 C1 H1 108.2 . . ?
N1 C1 H1 108.2 . . ?
C2 C1 H1 108.2 . . ?
C3 C2 C11 110.53(18) . . ?
C3 C2 C1 110.72(18) . . ?
C11 C2 C1 111.36(17) . . ?
C3 C2 H2 108.0 . . ?
C11 C2 H2 108.0 . . ?
C1 C2 H2 108.0 . . ?
C4 C3 C2 110.54(19) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 110.66(19) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C10 C5 C6 119.0(2) . . ?
C10 C5 C4 121.01(19) . . ?
C6 C5 C4 120.04(19) . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 O3 125.4(2) . . ?
C6 C7 C8 119.6(2) . . ?
O3 C7 C8 114.97(19) . . ?
O2 C8 C9 124.3(2) . . ?
O2 C8 C7 116.11(18) . . ?
C9 C8 C7 119.6(2) . . ?
C8 C9 C10 120.7(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C5 C10 C9 119.69(19) . . ?
C5 C10 C1 122.48(19) . . ?
C9 C10 C1 117.83(19) . . ?
C16 C11 C12 118.0(2) . . ?
C16 C11 C2 118.3(2) . . ?
C12 C11 C2 123.6(2) . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 P1 119.65(17) . . ?
C11 C12 P1 120.62(16) . . ?
C14 C13 C12 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 122.0(2) . . ?
C11 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C22 C17 C18 118.9(2) . . ?
C22 C17 P1 122.29(17) . . ?
C18 C17 P1 118.8(2) . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 119.6(3) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C17 120.8(3) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
C24 C23 C28 119.1(2) . . ?
C24 C23 P1 123.31(17) . . ?
C28 C23 P1 117.55(17) . . ?
C23 C24 C25 120.2(2) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 119.9(2) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.9(2) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C26 C27 C28 119.7(2) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C27 C28 C23 120.2(2) . . ?
C27 C28 H28 119.9 . . ?
C23 C28 H28 119.9 . . ?
O2 C29 H29A 109.5 . . ?
O2 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O2 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O3 C30 H30A 109.5 . . ?
O3 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O3 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 C33 121.4(5) . 2_667 ?
C39 C32 C31 127.8(10) . . ?
C39 C32 C33 111.0(10) . . ?
C31 C32 C33 120.6(5) . . ?
C40 C33 C31 121.5(9) . 2_667 ?
C40 C33 C32 120.0(9) . . ?
C31 C33 C32 118.0(5) 2_667 . ?
C35 C34 C36 51.2(6) . . ?
C35 C34 C38 57.5(6) . 2_656 ?
C36 C34 C38 108.6(7) . 2_656 ?
C36 C35 C34 70.4(9) . . ?
C36 C35 C38 139.1(11) . 2_656 ?
C34 C35 C38 68.7(6) . 2_656 ?
C36 C35 C37 60.3(7) . . ?
C34 C35 C37 130.7(10) . . ?
C38 C35 C37 160.4(10) 2_656 . ?
C36 C35 C37 169.0(9) . 2_656 ?
C34 C35 C37 120.2(7) . 2_656 ?
C38 C35 C37 51.5(6) 2_656 2_656 ?
C37 C35 C37 109.0(7) . 2_656 ?
C36 C35 C35 118.2(10) . 2_656 ?
C34 C35 C35 170.9(11) . 2_656 ?
C38 C35 C35 102.5(10) 2_656 2_656 ?
C37 C35 C35 58.0(5) . 2_656 ?
C37 C35 C35 51.0(6) 2_656 2_656 ?
C35 C36 C37 67.4(7) . . ?
C35 C36 C34 58.4(6) . . ?
C37 C36 C34 125.7(8) . . ?
C38 C37 C36 178.8(7) . . ?
C38 C37 C35 128.9(8) . . ?
C36 C37 C35 52.3(5) . . ?
C38 C37 C35 57.9(5) . 2_656 ?
C36 C37 C35 123.3(6) . 2_656 ?
C35 C37 C35 71.0(7) . 2_656 ?
C37 C38 C35 70.6(6) . 2_656 ?
C37 C38 C34 124.3(6) . 2_656 ?
C35 C38 C34 53.8(5) 2_656 2_656 ?
F3 B1 F4 110.6(3) . . ?
F3 B1 F2 112.1(2) . . ?
F4 B1 F2 109.2(3) . . ?
F3 B1 F1 110.4(3) . . ?
F4 B1 F1 107.6(2) . . ?
F2 B1 F1 106.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -31.7(3) . . . . ?
N1 C1 C2 C3 -153.07(18) . . . . ?
C10 C1 C2 C11 -155.1(2) . . . . ?
N1 C1 C2 C11 83.5(2) . . . . ?
C11 C2 C3 C4 -176.54(19) . . . . ?
C1 C2 C3 C4 59.6(3) . . . . ?
C2 C3 C4 C5 -56.8(3) . . . . ?
C3 C4 C5 C10 27.0(3) . . . . ?
C3 C4 C5 C6 -152.9(2) . . . . ?
C10 C5 C6 C7 0.9(4) . . . . ?
C4 C5 C6 C7 -179.2(2) . . . . ?
C5 C6 C7 O3 179.3(2) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C30 O3 C7 C6 1.0(3) . . . . ?
C30 O3 C7 C8 -179.4(2) . . . . ?
C29 O2 C8 C9 -4.0(3) . . . . ?
C29 O2 C8 C7 177.1(2) . . . . ?
C6 C7 C8 O2 177.8(2) . . . . ?
O3 C7 C8 O2 -1.9(3) . . . . ?
C6 C7 C8 C9 -1.1(4) . . . . ?
O3 C7 C8 C9 179.2(2) . . . . ?
O2 C8 C9 C10 -176.8(2) . . . . ?
C7 C8 C9 C10 2.0(4) . . . . ?
C6 C5 C10 C9 -0.1(3) . . . . ?
C4 C5 C10 C9 -179.9(2) . . . . ?
C6 C5 C10 C1 -179.8(2) . . . . ?
C4 C5 C10 C1 0.3(4) . . . . ?
C8 C9 C10 C5 -1.4(4) . . . . ?
C8 C9 C10 C1 178.3(2) . . . . ?
N1 C1 C10 C5 123.7(2) . . . . ?
C2 C1 C10 C5 2.1(3) . . . . ?
N1 C1 C10 C9 -56.0(3) . . . . ?
C2 C1 C10 C9 -177.6(2) . . . . ?
C3 C2 C11 C16 -53.1(3) . . . . ?
C1 C2 C11 C16 70.4(2) . . . . ?
C3 C2 C11 C12 124.5(2) . . . . ?
C1 C2 C11 C12 -111.9(2) . . . . ?
C16 C11 C12 C13 0.9(3) . . . . ?
C2 C11 C12 C13 -176.73(19) . . . . ?
C16 C11 C12 P1 -171.00(16) . . . . ?
C2 C11 C12 P1 11.3(3) . . . . ?
O1 P1 C12 C13 -117.38(18) . . . . ?
C23 P1 C12 C13 4.6(2) . . . . ?
C17 P1 C12 C13 119.85(18) . . . . ?
O1 P1 C12 C11 54.53(19) . . . . ?
C23 P1 C12 C11 176.54(16) . . . . ?
C17 P1 C12 C11 -68.24(19) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
P1 C12 C13 C14 171.80(17) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C13 C14 C15 C16 1.9(3) . . . . ?
C12 C11 C16 C15 -0.3(3) . . . . ?
C2 C11 C16 C15 177.5(2) . . . . ?
C14 C15 C16 C11 -1.2(3) . . . . ?
O1 P1 C17 C22 -162.5(2) . . . . ?
C23 P1 C17 C22 74.2(2) . . . . ?
C12 P1 C17 C22 -40.9(2) . . . . ?
O1 P1 C17 C18 19.0(2) . . . . ?
C23 P1 C17 C18 -104.35(19) . . . . ?
C12 P1 C17 C18 140.57(19) . . . . ?
C22 C17 C18 C19 -0.6(4) . . . . ?
P1 C17 C18 C19 178.03(19) . . . . ?
C17 C18 C19 C20 -0.6(4) . . . . ?
C18 C19 C20 C21 1.5(5) . . . . ?
C19 C20 C21 C22 -1.3(5) . . . . ?
C20 C21 C22 C17 0.2(4) . . . . ?
C18 C17 C22 C21 0.8(4) . . . . ?
P1 C17 C22 C21 -177.8(2) . . . . ?
O1 P1 C23 C24 -131.9(2) . . . . ?
C17 P1 C23 C24 -8.8(2) . . . . ?
C12 P1 C23 C24 107.6(2) . . . . ?
O1 P1 C23 C28 47.9(2) . . . . ?
C17 P1 C23 C28 170.97(18) . . . . ?
C12 P1 C23 C28 -72.7(2) . . . . ?
C28 C23 C24 C25 1.4(3) . . . . ?
P1 C23 C24 C25 -178.80(17) . . . . ?
C23 C24 C25 C26 -0.4(4) . . . . ?
C24 C25 C26 C27 -0.7(4) . . . . ?
C25 C26 C27 C28 0.8(4) . . . . ?
C26 C27 C28 C23 0.3(4) . . . . ?
C24 C23 C28 C27 -1.4(3) . . . . ?
P1 C23 C28 C27 178.82(18) . . . . ?
C33 C31 C32 C39 170.0(9) 2_667 . . . ?
C33 C31 C32 C33 -0.3(6) 2_667 . . . ?
C39 C32 C33 C40 17.0(11) . . . . ?
C31 C32 C33 C40 -171.3(8) . . . . ?
C39 C32 C33 C31 -171.5(7) . . . 2_667 ?
C31 C32 C33 C31 0.2(6) . . . 2_667 ?
C38 C34 C35 C36 -177.2(6) 2_656 . . . ?
C36 C34 C35 C38 177.2(6) . . . 2_656 ?
C36 C34 C35 C37 0.3(6) . . . . ?
C38 C34 C35 C37 -176.8(8) 2_656 . . . ?
C36 C34 C35 C37 176.9(8) . . . 2_656 ?
C38 C34 C35 C37 -0.2(5) 2_656 . . 2_656 ?
C34 C35 C36 C37 179.7(5) . . . . ?
C38 C35 C36 C37 175.7(10) 2_656 . . . ?
C37 C35 C36 C37 14(4) 2_656 . . . ?
C35 C35 C36 C37 2.6(7) 2_656 . . . ?
C38 C35 C36 C34 -4.0(9) 2_656 . . . ?
C37 C35 C36 C34 -179.7(5) . . . . ?
C37 C35 C36 C34 -166(4) 2_656 . . . ?
C35 C35 C36 C34 -177.1(8) 2_656 . . . ?
C38 C34 C36 C35 2.5(6) 2_656 . . . ?
C35 C34 C36 C37 -0.3(6) . . . . ?
C38 C34 C36 C37 2.2(9) 2_656 . . . ?
C34 C36 C37 C35 0.3(5) . . . . ?
C35 C36 C37 C35 -3.1(8) . . . 2_656 ?
C34 C36 C37 C35 -2.8(10) . . . 2_656 ?
C36 C35 C37 C38 179.9(7) . . . . ?
C34 C35 C37 C38 179.6(6) . . . . ?
C38 C35 C37 C38 8(2) 2_656 . . . ?
C37 C35 C37 C38 2.7(7) 2_656 . . . ?
C35 C35 C37 C38 2.7(7) 2_656 . . . ?
C34 C35 C37 C36 -0.4(6) . . . . ?
C38 C35 C37 C36 -171.5(19) 2_656 . . . ?
C37 C35 C37 C36 -177.3(7) 2_656 . . . ?
C35 C35 C37 C36 -177.3(7) 2_656 . . . ?
C36 C35 C37 C35 177.3(7) . . . 2_656 ?
C34 C35 C37 C35 176.9(9) . . . 2_656 ?
C38 C35 C37 C35 5.7(15) 2_656 . . 2_656 ?
C37 C35 C37 C35 0.002(0) 2_656 . . 2_656 ?
C35 C37 C38 C35 -3.0(8) . . . 2_656 ?
C35 C37 C38 C34 -2.7(10) . . . 2_656 ?
C35 C37 C38 C34 0.2(5) 2_656 . . 2_656 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O2 . . 2_666 3.055(2) 0.910 2.154 170.6 no
N1 H1A O3 . . 2_666 3.061(3) 0.910 2.582 113.5 no
N1 H1B O1 . . . 2.676(2) 0.910 1.803 159.8 no
N1 H1C F1 . . . 2.880(3) 0.910 1.998 163.0 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


