# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 
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data_jcs062_compound_2a
_database_code_depnum_ccdc_archive 'CCDC 1555966'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ((di-tert-butylphosphonio)methyl)diphenyl(phenylethynyl)borate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H36 B P'
_chemical_formula_sum            'C29 H36 B P'
_chemical_formula_weight         426.36

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.9924(6)
_cell_length_b                   16.5973(5)
_cell_length_c                   17.5163(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4940.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      4.5
_cell_measurement_theta_max      72.1

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.061
_shelx_estimated_absorpt_T_min   0.816
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7887
_exptl_absorpt_correction_T_max  0.9582
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   .

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 9+1 runs, 1476 frames, 16/32 sec./frame
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with Photon100 detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            39211
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.499
_diffrn_reflns_theta_max         72.167
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4859
_reflns_number_gt                4380
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       APEX3
_computing_cell_refinement       APEX3
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Shelxtl
_computing_publication_material  publCIF

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0554P)²+1.7627P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4859
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.73668(2) 0.59082(2) 0.75101(2) 0.01404(10) Uani 1 1 d . . . . .
H1 H 0.7003(9) 0.6086(9) 0.6900(9) 0.025(4) Uiso 1 1 d . . . . .
C1 C 0.80635(7) 0.51310(7) 0.73055(7) 0.0166(2) Uani 1 1 d . . . . .
H1A H 0.8600 0.5352 0.7375 0.020 Uiso 1 1 calc R U . . .
H1B H 0.7993 0.4692 0.7682 0.020 Uiso 1 1 calc R U . . .
B1 B 0.79967(8) 0.47350(8) 0.64165(7) 0.0158(3) Uani 1 1 d . . . . .
C2 C 0.78653(7) 0.68671(7) 0.77493(7) 0.0184(2) Uani 1 1 d . . . . .
C3 C 0.84447(8) 0.67614(8) 0.84141(8) 0.0252(3) Uani 1 1 d . . . . .
H3A H 0.8824 0.6336 0.8289 0.038 Uiso 1 1 calc R U . . .
H3B H 0.8726 0.7269 0.8502 0.038 Uiso 1 1 calc R U . . .
H3C H 0.8155 0.6612 0.8876 0.038 Uiso 1 1 calc R U . . .
C4 C 0.83252(8) 0.71171(8) 0.70313(7) 0.0242(3) Uani 1 1 d . . . . .
H4A H 0.8714 0.6701 0.6907 0.036 Uiso 1 1 calc R U . . .
H4B H 0.7960 0.7181 0.6603 0.036 Uiso 1 1 calc R U . . .
H4C H 0.8595 0.7629 0.7126 0.036 Uiso 1 1 calc R U . . .
C5 C 0.72629(8) 0.75295(7) 0.79283(8) 0.0245(3) Uani 1 1 d . . . . .
H5A H 0.6899 0.7587 0.7498 0.037 Uiso 1 1 calc R U . . .
H5B H 0.6967 0.7384 0.8388 0.037 Uiso 1 1 calc R U . . .
H5C H 0.7538 0.8041 0.8014 0.037 Uiso 1 1 calc R U . . .
C6 C 0.65790(7) 0.55918(7) 0.81840(7) 0.0202(3) Uani 1 1 d . . . . .
C7 C 0.68034(9) 0.57566(9) 0.90165(7) 0.0279(3) Uani 1 1 d . . . . .
H7A H 0.7285 0.5461 0.9143 0.042 Uiso 1 1 calc R U . . .
H7B H 0.6893 0.6335 0.9087 0.042 Uiso 1 1 calc R U . . .
H7C H 0.6376 0.5580 0.9352 0.042 Uiso 1 1 calc R U . . .
C8 C 0.58257(8) 0.60464(9) 0.79647(8) 0.0295(3) Uani 1 1 d . . . . .
H8A H 0.5694 0.5932 0.7431 0.044 Uiso 1 1 calc R U . . .
H8B H 0.5392 0.5871 0.8294 0.044 Uiso 1 1 calc R U . . .
H8C H 0.5909 0.6627 0.8029 0.044 Uiso 1 1 calc R U . . .
C9 C 0.64309(9) 0.46818(8) 0.80987(9) 0.0319(3) Uani 1 1 d . . . . .
H9A H 0.6286 0.4561 0.7569 0.048 Uiso 1 1 calc R U . . .
H9B H 0.6910 0.4386 0.8233 0.048 Uiso 1 1 calc R U . . .
H9C H 0.6002 0.4519 0.8440 0.048 Uiso 1 1 calc R U . . .
C10 C 0.85090(7) 0.39031(7) 0.64066(7) 0.0167(2) Uani 1 1 d . . . . .
C11 C 0.91790(7) 0.37829(7) 0.68607(7) 0.0205(3) Uani 1 1 d . . . . .
H11 H 0.9336 0.4197 0.7202 0.025 Uiso 1 1 calc R U . . .
C12 C 0.96217(8) 0.30780(8) 0.68288(8) 0.0245(3) Uani 1 1 d . . . . .
H12 H 1.0072 0.3018 0.7145 0.029 Uiso 1 1 calc R U . . .
C13 C 0.94061(8) 0.24622(7) 0.63352(8) 0.0262(3) Uani 1 1 d . . . . .
H13 H 0.9709 0.1982 0.6307 0.031 Uiso 1 1 calc R U . . .
C14 C 0.87421(8) 0.25573(7) 0.58844(7) 0.0247(3) Uani 1 1 d . . . . .
H14 H 0.8585 0.2137 0.5549 0.030 Uiso 1 1 calc R U . . .
C15 C 0.83055(7) 0.32639(7) 0.59206(7) 0.0198(2) Uani 1 1 d . . . . .
H15 H 0.7853 0.3316 0.5605 0.024 Uiso 1 1 calc R U . . .
C16 C 0.83471(7) 0.53936(7) 0.58104(6) 0.0153(2) Uani 1 1 d . . . . .
C17 C 0.91576(7) 0.54697(7) 0.56819(7) 0.0185(2) Uani 1 1 d . . . . .
H17 H 0.9506 0.5102 0.5924 0.022 Uiso 1 1 calc R U . . .
C18 C 0.94705(7) 0.60647(8) 0.52125(7) 0.0221(3) Uani 1 1 d . . . . .
H18 H 1.0023 0.6096 0.5136 0.027 Uiso 1 1 calc R U . . .
C19 C 0.89759(8) 0.66132(8) 0.48560(7) 0.0235(3) Uani 1 1 d . . . . .
H19 H 0.9188 0.7030 0.4547 0.028 Uiso 1 1 calc R U . . .
C20 C 0.81682(8) 0.65454(8) 0.49566(7) 0.0222(3) Uani 1 1 d . . . . .
H20 H 0.7824 0.6913 0.4709 0.027 Uiso 1 1 calc R U . . .
C21 C 0.78627(7) 0.59389(7) 0.54198(7) 0.0183(2) Uani 1 1 d . . . . .
H21 H 0.7308 0.5893 0.5473 0.022 Uiso 1 1 calc R U . . .
C22 C 0.70984(7) 0.45511(7) 0.62248(7) 0.0185(2) Uani 1 1 d . . . . .
C23 C 0.64118(7) 0.44256(7) 0.60883(7) 0.0209(3) Uani 1 1 d . . . . .
C24 C 0.55910(7) 0.42462(8) 0.59829(7) 0.0201(3) Uani 1 1 d . . . . .
C25 C 0.53390(8) 0.34467(8) 0.59105(8) 0.0265(3) Uani 1 1 d . . . . .
H25 H 0.5715 0.3023 0.5915 0.032 Uiso 1 1 calc R U . . .
C26 C 0.45482(9) 0.32686(9) 0.58323(9) 0.0326(3) Uani 1 1 d . . . . .
H26 H 0.4384 0.2723 0.5788 0.039 Uiso 1 1 calc R U . . .
C27 C 0.39938(8) 0.38804(9) 0.58182(8) 0.0303(3) Uani 1 1 d . . . . .
H27 H 0.3450 0.3756 0.5771 0.036 Uiso 1 1 calc R U . . .
C28 C 0.42356(8) 0.46729(9) 0.58724(8) 0.0302(3) Uani 1 1 d . . . . .
H28 H 0.3858 0.5094 0.5851 0.036 Uiso 1 1 calc R U . . .
C29 C 0.50269(8) 0.48577(8) 0.59579(8) 0.0271(3) Uani 1 1 d . . . . .
H29 H 0.5186 0.5404 0.6000 0.032 Uiso 1 1 calc R U . . .


_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 1.7871(12) . ?
P1 C2 1.8508(12) . ?
P1 C6 1.8606(12) . ?
P1 H1 1.270(15) . ?
C1 B1 1.6942(17) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
B1 C22 1.5924(17) . ?
B1 C10 1.6323(16) . ?
B1 C16 1.6359(17) . ?
C2 C5 1.5345(16) . ?
C2 C3 1.5350(17) . ?
C2 C4 1.5378(17) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.5318(18) . ?
C6 C8 1.5347(18) . ?
C6 C9 1.5385(18) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.4031(17) . ?
C10 C15 1.4035(16) . ?
C11 C12 1.3920(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3879(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3892(18) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.4013(17) . ?
C16 C21 1.4017(16) . ?
C17 C18 1.3907(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.3876(18) . ?
C18 H18 0.9500 . ?
C19 C20 1.3883(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.3932(17) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.2091(18) . ?
C23 C24 1.4380(17) . ?
C24 C29 1.3967(19) . ?
C24 C25 1.4001(18) . ?
C25 C26 1.383(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.385(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.381(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.3873(19) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 C2 111.28(6) . . ?
C1 P1 C6 113.58(5) . . ?
C2 P1 C6 115.36(6) . . ?
C1 P1 H1 108.8(7) . . ?
C2 P1 H1 102.4(7) . . ?
C6 P1 H1 104.4(7) . . ?
B1 C1 P1 114.83(8) . . ?
B1 C1 H1A 108.6 . . ?
P1 C1 H1A 108.6 . . ?
B1 C1 H1B 108.6 . . ?
P1 C1 H1B 108.6 . . ?
H1A C1 H1B 107.5 . . ?
C22 B1 C10 110.30(9) . . ?
C22 B1 C16 109.88(10) . . ?
C10 B1 C16 111.36(9) . . ?
C22 B1 C1 109.41(9) . . ?
C10 B1 C1 107.59(9) . . ?
C16 B1 C1 108.23(9) . . ?
C5 C2 C3 110.77(10) . . ?
C5 C2 C4 108.23(10) . . ?
C3 C2 C4 108.99(10) . . ?
C5 C2 P1 110.92(9) . . ?
C3 C2 P1 111.53(8) . . ?
C4 C2 P1 106.22(8) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C8 110.98(11) . . ?
C7 C6 C9 107.97(11) . . ?
C8 C6 C9 108.78(12) . . ?
C7 C6 P1 111.99(9) . . ?
C8 C6 P1 107.61(8) . . ?
C9 C6 P1 109.46(9) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 115.87(11) . . ?
C11 C10 B1 123.16(10) . . ?
C15 C10 B1 120.95(11) . . ?
C12 C11 C10 122.37(11) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C13 C12 C11 120.08(12) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 119.07(12) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 120.32(12) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 122.29(12) . . ?
C14 C15 H15 118.9 . . ?
C10 C15 H15 118.9 . . ?
C17 C16 C21 116.13(11) . . ?
C17 C16 B1 121.48(10) . . ?
C21 C16 B1 122.31(10) . . ?
C18 C17 C16 122.33(11) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C19 C18 C17 120.03(12) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 119.24(11) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C19 C20 C21 120.06(12) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 122.14(12) . . ?
C20 C21 H21 118.9 . . ?
C16 C21 H21 118.9 . . ?
C23 C22 B1 178.61(13) . . ?
C22 C23 C24 175.54(13) . . ?
C29 C24 C25 118.42(12) . . ?
C29 C24 C23 121.27(12) . . ?
C25 C24 C23 120.30(12) . . ?
C26 C25 C24 120.58(13) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 120.40(13) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C28 C27 C26 119.64(13) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C29 120.41(13) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C28 C29 C24 120.53(13) . . ?
C28 C29 H29 119.7 . . ?
C24 C29 H29 119.7 . . ?

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
C2 P1 C1 B1 -119.78(8) . . . . ?
C6 P1 C1 B1 108.04(9) . . . . ?
P1 C1 B1 C22 -46.06(11) . . . . ?
P1 C1 B1 C10 -165.90(8) . . . . ?
P1 C1 B1 C16 73.66(11) . . . . ?
C1 P1 C2 C5 -179.69(8) . . . . ?
C6 P1 C2 C5 -48.41(10) . . . . ?
C1 P1 C2 C3 -55.70(10) . . . . ?
C6 P1 C2 C3 75.58(10) . . . . ?
C1 P1 C2 C4 62.93(10) . . . . ?
C6 P1 C2 C4 -165.80(8) . . . . ?
C1 P1 C6 C7 90.34(10) . . . . ?
C2 P1 C6 C7 -39.84(11) . . . . ?
C1 P1 C6 C8 -147.43(9) . . . . ?
C2 P1 C6 C8 82.40(10) . . . . ?
C1 P1 C6 C9 -29.37(11) . . . . ?
C2 P1 C6 C9 -159.55(9) . . . . ?
C22 B1 C10 C11 -150.06(11) . . . . ?
C16 B1 C10 C11 87.66(13) . . . . ?
C1 B1 C10 C11 -30.79(15) . . . . ?
C22 B1 C10 C15 31.29(15) . . . . ?
C16 B1 C10 C15 -90.99(13) . . . . ?
C1 B1 C10 C15 150.57(10) . . . . ?
C15 C10 C11 C12 0.59(18) . . . . ?
B1 C10 C11 C12 -178.12(11) . . . . ?
C10 C11 C12 C13 0.02(19) . . . . ?
C11 C12 C13 C14 -0.72(19) . . . . ?
C12 C13 C14 C15 0.79(19) . . . . ?
C13 C14 C15 C10 -0.16(19) . . . . ?
C11 C10 C15 C14 -0.51(17) . . . . ?
B1 C10 C15 C14 178.23(11) . . . . ?
C22 B1 C16 C17 -158.85(10) . . . . ?
C10 B1 C16 C17 -36.33(14) . . . . ?
C1 B1 C16 C17 81.73(13) . . . . ?
C22 B1 C16 C21 24.40(15) . . . . ?
C10 B1 C16 C21 146.92(11) . . . . ?
C1 B1 C16 C21 -95.02(12) . . . . ?
C21 C16 C17 C18 1.81(17) . . . . ?
B1 C16 C17 C18 -175.13(11) . . . . ?
C16 C17 C18 C19 0.44(19) . . . . ?
C17 C18 C19 C20 -1.82(19) . . . . ?
C18 C19 C20 C21 0.90(19) . . . . ?
C19 C20 C21 C16 1.47(19) . . . . ?
C17 C16 C21 C20 -2.76(17) . . . . ?
B1 C16 C21 C20 174.15(11) . . . . ?
C29 C24 C25 C26 -1.3(2) . . . . ?
C23 C24 C25 C26 178.02(12) . . . . ?
C24 C25 C26 C27 0.5(2) . . . . ?
C25 C26 C27 C28 0.9(2) . . . . ?
C26 C27 C28 C29 -1.4(2) . . . . ?
C27 C28 C29 C24 0.6(2) . . . . ?
C25 C24 C29 C28 0.8(2) . . . . ?
C23 C24 C29 C28 -178.59(13) . . . . ?

_refine_diff_density_max         0.326
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_jcs071_compound_7b
_database_code_depnum_ccdc_archive 'CCDC 1555972'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'4,4,5-tri-tert-butyl-1,2,2-triphenyl-3,4-dihydro-2H-1λ⁴,4,2λ⁴-azaphosphaborol-4-ium trifluoromethanesulfonate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H44 B N P, C F3 O3 S'
_chemical_formula_sum            'C33 H44 B F3 N O3 P S'
_chemical_formula_weight         633.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   13.6317(8)
_cell_length_b                   11.9518(8)
_cell_length_c                   19.7278(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.210(2)
_cell_angle_gamma                90
_cell_volume                     3152.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9500
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      27.5

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.206
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9219
_exptl_absorpt_correction_T_max  0.9586
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 50 mm, 1 deg., 10+1 runs, 1543 frames, 10 sec./frame
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with Photon100 detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            63370
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.105
_diffrn_reflns_theta_max         27.547
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7264
_reflns_number_gt                7090
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       APEX3
_computing_cell_refinement       APEX3
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Shelxtl
_computing_publication_material  publCIF

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²+1.9794P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 3412 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.015(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7264
_refine_ls_number_parameters     389
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0682
_refine_ls_wR_factor_gt          0.0674
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.15961(3) 0.39544(4) 0.55095(3) 0.00948(11) Uani 1 1 d . . . . .
C1 C 0.11397(15) 0.51173(16) 0.49758(10) 0.0121(4) Uani 1 1 d . . . . .
H1A H 0.0409 0.5041 0.4810 0.015 Uiso 1 1 calc R U . . .
H1B H 0.1264 0.5818 0.5247 0.015 Uiso 1 1 calc R U . . .
B1 B 0.17048(17) 0.51738(19) 0.43135(11) 0.0110(4) Uani 1 1 d . . . . .
N1 N 0.25181(12) 0.41268(14) 0.44793(8) 0.0098(3) Uani 1 1 d . . . . .
C2 C 0.24145(15) 0.44999(18) 0.63149(11) 0.0141(4) Uani 1 1 d . . . . .
C3 C 0.30084(18) 0.3611(2) 0.67850(11) 0.0210(5) Uani 1 1 d . . . . .
H3A H 0.2544 0.3079 0.6932 0.032 Uiso 1 1 calc R U . . .
H3B H 0.3451 0.3212 0.6531 0.032 Uiso 1 1 calc R U . . .
H3C H 0.3409 0.3974 0.7192 0.032 Uiso 1 1 calc R U . . .
C4 C 0.17323(17) 0.51302(19) 0.67239(11) 0.0180(4) Uani 1 1 d . . . . .
H4A H 0.1349 0.5701 0.6428 0.027 Uiso 1 1 calc R U . . .
H4B H 0.1271 0.4600 0.6876 0.027 Uiso 1 1 calc R U . . .
H4C H 0.2143 0.5491 0.7128 0.027 Uiso 1 1 calc R U . . .
C5 C 0.31633(17) 0.53213(19) 0.60928(12) 0.0193(4) Uani 1 1 d . . . . .
H5A H 0.2798 0.5897 0.5791 0.029 Uiso 1 1 calc R U . . .
H5B H 0.3563 0.5676 0.6503 0.029 Uiso 1 1 calc R U . . .
H5C H 0.3606 0.4914 0.5843 0.029 Uiso 1 1 calc R U . . .
C6 C 0.04946(15) 0.30884(17) 0.56379(11) 0.0149(4) Uani 1 1 d . . . . .
C7 C -0.03355(16) 0.39162(19) 0.57449(12) 0.0190(4) Uani 1 1 d . . . . .
H7A H -0.0112 0.4337 0.6173 0.029 Uiso 1 1 calc R U . . .
H7B H -0.0475 0.4436 0.5354 0.029 Uiso 1 1 calc R U . . .
H7C H -0.0944 0.3499 0.5775 0.029 Uiso 1 1 calc R U . . .
C8 C 0.06814(18) 0.2310(2) 0.62689(13) 0.0222(5) Uani 1 1 d . . . . .
H8A H 0.0915 0.2751 0.6688 0.033 Uiso 1 1 calc R U . . .
H8B H 0.0058 0.1927 0.6306 0.033 Uiso 1 1 calc R U . . .
H8C H 0.1190 0.1754 0.6216 0.033 Uiso 1 1 calc R U . . .
C9 C 0.01258(17) 0.24412(19) 0.49646(12) 0.0213(5) Uani 1 1 d . . . . .
H9A H 0.0015 0.2964 0.4574 0.032 Uiso 1 1 calc R U . . .
H9B H 0.0629 0.1887 0.4900 0.032 Uiso 1 1 calc R U . . .
H9C H -0.0503 0.2060 0.4990 0.032 Uiso 1 1 calc R U . . .
C10 C 0.09097(15) 0.48481(17) 0.36116(10) 0.0125(4) Uani 1 1 d . . . . .
C11 C 0.03030(16) 0.57074(19) 0.32739(12) 0.0181(4) Uani 1 1 d . . . . .
H11 H 0.0406 0.6451 0.3444 0.022 Uiso 1 1 calc R U . . .
C12 C -0.04446(17) 0.5507(2) 0.26993(12) 0.0213(5) Uani 1 1 d . . . . .
H12 H -0.0852 0.6106 0.2490 0.026 Uiso 1 1 calc R U . . .
C13 C -0.05970(16) 0.4436(2) 0.24315(12) 0.0215(5) Uani 1 1 d . . . . .
H13 H -0.1099 0.4300 0.2033 0.026 Uiso 1 1 calc R U . . .
C14 C -0.00126(17) 0.3567(2) 0.27484(12) 0.0197(4) Uani 1 1 d . . . . .
H14 H -0.0104 0.2832 0.2564 0.024 Uiso 1 1 calc R U . . .
C15 C 0.07138(15) 0.37718(17) 0.33404(11) 0.0149(4) Uani 1 1 d . . . . .
H15 H 0.1087 0.3160 0.3566 0.018 Uiso 1 1 calc R U . . .
C16 C 0.22279(15) 0.63621(17) 0.42098(10) 0.0121(4) Uani 1 1 d . . . . .
C17 C 0.21684(15) 0.72916(17) 0.46308(10) 0.0142(4) Uani 1 1 d . . . . .
H17 H 0.1903 0.7197 0.5038 0.017 Uiso 1 1 calc R U . . .
C18 C 0.24872(16) 0.83547(17) 0.44721(11) 0.0165(4) Uani 1 1 d . . . . .
H18 H 0.2433 0.8968 0.4769 0.020 Uiso 1 1 calc R U . . .
C19 C 0.28809(18) 0.85158(18) 0.38859(12) 0.0197(4) Uani 1 1 d . . . . .
H19 H 0.3097 0.9237 0.3776 0.024 Uiso 1 1 calc R U . . .
C20 C 0.29570(17) 0.76121(19) 0.34598(11) 0.0191(4) Uani 1 1 d . . . . .
H20 H 0.3233 0.7711 0.3057 0.023 Uiso 1 1 calc R U . . .
C21 C 0.26304(16) 0.65624(18) 0.36192(11) 0.0158(4) Uani 1 1 d . . . . .
H21 H 0.2682 0.5956 0.3316 0.019 Uiso 1 1 calc R U . . .
C22 C 0.24529(14) 0.33761(16) 0.49420(10) 0.0108(4) Uani 1 1 d . . . . .
C23 C 0.30205(15) 0.22520(17) 0.50446(11) 0.0139(4) Uani 1 1 d . . . . .
C24 C 0.26431(17) 0.15230(18) 0.55775(12) 0.0178(4) Uani 1 1 d . . . . .
H24A H 0.2749 0.1914 0.6022 0.027 Uiso 1 1 calc R U . . .
H24B H 0.1928 0.1374 0.5421 0.027 Uiso 1 1 calc R U . . .
H24C H 0.3010 0.0813 0.5631 0.027 Uiso 1 1 calc R U . . .
C25 C 0.2825(2) 0.1576(2) 0.43668(13) 0.0284(6) Uani 1 1 d . . . . .
H25A H 0.3054 0.2006 0.4004 0.043 Uiso 1 1 calc R U . . .
H25B H 0.3190 0.0866 0.4437 0.043 Uiso 1 1 calc R U . . .
H25C H 0.2107 0.1427 0.4228 0.043 Uiso 1 1 calc R U . . .
C26 C 0.41559(17) 0.2419(2) 0.52918(16) 0.0287(6) Uani 1 1 d . . . . .
H26A H 0.4416 0.2885 0.4958 0.043 Uiso 1 1 calc R U . . .
H26B H 0.4282 0.2789 0.5744 0.043 Uiso 1 1 calc R U . . .
H26C H 0.4491 0.1690 0.5331 0.043 Uiso 1 1 calc R U . . .
C27 C 0.33192(15) 0.40914(17) 0.40817(10) 0.0127(4) Uani 1 1 d . . . . .
C28 C 0.42271(16) 0.45621(18) 0.43885(12) 0.0180(4) Uani 1 1 d . . . . .
H28 H 0.4308 0.4891 0.4834 0.022 Uiso 1 1 calc R U . . .
C29 C 0.50170(17) 0.4547(2) 0.40373(13) 0.0237(5) Uani 1 1 d . . . . .
H29 H 0.5643 0.4861 0.4246 0.028 Uiso 1 1 calc R U . . .
C30 C 0.48956(19) 0.4078(2) 0.33863(14) 0.0263(5) Uani 1 1 d . . . . .
H30 H 0.5443 0.4052 0.3153 0.032 Uiso 1 1 calc R U . . .
C31 C 0.39749(19) 0.3647(2) 0.30733(12) 0.0221(5) Uani 1 1 d . . . . .
H31 H 0.3891 0.3336 0.2622 0.027 Uiso 1 1 calc R U . . .
C32 C 0.31725(17) 0.36655(17) 0.34158(11) 0.0160(4) Uani 1 1 d . . . . .
H32 H 0.2535 0.3391 0.3197 0.019 Uiso 1 1 calc R U . . .
S1 S 0.15898(4) 0.88163(4) 0.62680(3) 0.01723(12) Uani 1 1 d . . . . .
O1 O 0.26388(14) 0.90034(18) 0.63065(11) 0.0348(4) Uani 1 1 d . . . . .
O2 O 0.09494(14) 0.95799(15) 0.58216(9) 0.0296(4) Uani 1 1 d . . . . .
O3 O 0.12703(15) 0.76696(15) 0.62163(10) 0.0331(4) Uani 1 1 d . . . . .
C1T C 0.14150(18) 0.9227(2) 0.71254(12) 0.0223(5) Uani 1 1 d . . . . .
F1 F 0.17274(13) 1.02701(13) 0.72825(8) 0.0340(4) Uani 1 1 d . . . . .
F2 F 0.04484(13) 0.91762(18) 0.71698(10) 0.0445(5) Uani 1 1 d . . . . .
F3 F 0.19068(15) 0.85616(15) 0.76155(8) 0.0429(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.781(2) . ?
P1 C2 1.872(2) . ?
P1 C6 1.881(2) . ?
P1 C22 1.898(2) . ?
C1 B1 1.642(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
B1 C16 1.620(3) . ?
B1 C10 1.631(3) . ?
B1 N1 1.662(3) . ?
N1 C22 1.295(3) . ?
N1 C27 1.464(3) . ?
C2 C3 1.534(3) . ?
C2 C5 1.540(3) . ?
C2 C4 1.541(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C9 1.535(3) . ?
C6 C8 1.535(3) . ?
C6 C7 1.548(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.399(3) . ?
C10 C11 1.403(3) . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.398(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.399(3) . ?
C16 C21 1.402(3) . ?
C17 C18 1.398(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.544(3) . ?
C23 C24 1.529(3) . ?
C23 C25 1.540(3) . ?
C23 C26 1.543(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C32 1.387(3) . ?
C27 C28 1.387(3) . ?
C28 C29 1.389(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.382(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.386(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.393(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
S1 O1 1.4346(19) . ?
S1 O3 1.4356(19) . ?
S1 O2 1.4394(18) . ?
S1 C1T 1.821(2) . ?
C1T F3 1.328(3) . ?
C1T F1 1.335(3) . ?
C1T F2 1.339(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 C2 108.18(10) . . ?
C1 P1 C6 108.22(10) . . ?
C2 P1 C6 115.91(10) . . ?
C1 P1 C22 96.88(9) . . ?
C2 P1 C22 107.09(9) . . ?
C6 P1 C22 118.54(9) . . ?
B1 C1 P1 109.78(13) . . ?
B1 C1 H1A 109.7 . . ?
P1 C1 H1A 109.7 . . ?
B1 C1 H1B 109.7 . . ?
P1 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C16 B1 C10 109.77(16) . . ?
C16 B1 C1 115.00(17) . . ?
C10 B1 C1 109.18(16) . . ?
C16 B1 N1 113.07(16) . . ?
C10 B1 N1 107.17(16) . . ?
C1 B1 N1 102.17(15) . . ?
C22 N1 C27 121.21(17) . . ?
C22 N1 B1 121.72(16) . . ?
C27 N1 B1 117.07(15) . . ?
C3 C2 C5 108.21(18) . . ?
C3 C2 C4 108.86(18) . . ?
C5 C2 C4 109.76(18) . . ?
C3 C2 P1 115.43(15) . . ?
C5 C2 P1 107.41(14) . . ?
C4 C2 P1 107.09(14) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C9 C6 C8 111.78(18) . . ?
C9 C6 C7 108.36(18) . . ?
C8 C6 C7 106.69(17) . . ?
C9 C6 P1 107.26(14) . . ?
C8 C6 P1 115.58(15) . . ?
C7 C6 P1 106.88(14) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 116.14(19) . . ?
C15 C10 B1 126.16(18) . . ?
C11 C10 B1 117.49(18) . . ?
C12 C11 C10 122.1(2) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 122.1(2) . . ?
C14 C15 H15 118.9 . . ?
C10 C15 H15 118.9 . . ?
C17 C16 C21 115.79(18) . . ?
C17 C16 B1 122.93(18) . . ?
C21 C16 B1 120.52(18) . . ?
C18 C17 C16 122.16(19) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.2(2) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C19 C20 C21 120.2(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 122.5(2) . . ?
C20 C21 H21 118.7 . . ?
C16 C21 H21 118.7 . . ?
N1 C22 C23 126.43(18) . . ?
N1 C22 P1 107.33(14) . . ?
C23 C22 P1 126.13(14) . . ?
C24 C23 C25 105.88(18) . . ?
C24 C23 C26 107.90(18) . . ?
C25 C23 C26 109.6(2) . . ?
C24 C23 C22 111.03(17) . . ?
C25 C23 C22 110.16(17) . . ?
C26 C23 C22 112.03(17) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 C27 C28 121.0(2) . . ?
C32 C27 N1 122.21(18) . . ?
C28 C27 N1 116.74(18) . . ?
C27 C28 C29 119.3(2) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C30 C29 C28 120.3(2) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 120.0(2) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 C32 120.4(2) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C27 C32 C31 118.9(2) . . ?
C27 C32 H32 120.6 . . ?
C31 C32 H32 120.6 . . ?
O1 S1 O3 115.98(12) . . ?
O1 S1 O2 114.41(12) . . ?
O3 S1 O2 114.98(11) . . ?
O1 S1 C1T 102.59(12) . . ?
O3 S1 C1T 103.32(12) . . ?
O2 S1 C1T 102.97(11) . . ?
F3 C1T F1 107.3(2) . . ?
F3 C1T F2 106.8(2) . . ?
F1 C1T F2 107.5(2) . . ?
F3 C1T S1 112.11(18) . . ?
F1 C1T S1 111.95(16) . . ?
F2 C1T S1 110.91(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 P1 C1 B1 106.97(14) . . . . ?
C6 P1 C1 B1 -126.70(14) . . . . ?
C22 P1 C1 B1 -3.58(15) . . . . ?
P1 C1 B1 C16 -126.23(16) . . . . ?
P1 C1 B1 C10 109.90(16) . . . . ?
P1 C1 B1 N1 -3.35(17) . . . . ?
C16 B1 N1 C22 138.10(18) . . . . ?
C10 B1 N1 C22 -100.8(2) . . . . ?
C1 B1 N1 C22 13.9(2) . . . . ?
C16 B1 N1 C27 -41.5(2) . . . . ?
C10 B1 N1 C27 79.6(2) . . . . ?
C1 B1 N1 C27 -165.71(16) . . . . ?
C1 P1 C2 C3 -170.65(16) . . . . ?
C6 P1 C2 C3 67.65(18) . . . . ?
C22 P1 C2 C3 -67.19(18) . . . . ?
C1 P1 C2 C5 -49.87(17) . . . . ?
C6 P1 C2 C5 -171.58(14) . . . . ?
C22 P1 C2 C5 53.59(16) . . . . ?
C1 P1 C2 C4 67.97(16) . . . . ?
C6 P1 C2 C4 -53.73(17) . . . . ?
C22 P1 C2 C4 171.44(14) . . . . ?
C1 P1 C6 C9 75.37(16) . . . . ?
C2 P1 C6 C9 -162.95(14) . . . . ?
C22 P1 C6 C9 -33.45(18) . . . . ?
C1 P1 C6 C8 -159.22(16) . . . . ?
C2 P1 C6 C8 -37.54(19) . . . . ?
C22 P1 C6 C8 91.96(17) . . . . ?
C1 P1 C6 C7 -40.67(17) . . . . ?
C2 P1 C6 C7 81.01(16) . . . . ?
C22 P1 C6 C7 -149.49(14) . . . . ?
C16 B1 C10 C15 144.0(2) . . . . ?
C1 B1 C10 C15 -89.1(2) . . . . ?
N1 B1 C10 C15 20.8(3) . . . . ?
C16 B1 C10 C11 -41.6(2) . . . . ?
C1 B1 C10 C11 85.3(2) . . . . ?
N1 B1 C10 C11 -164.73(17) . . . . ?
C15 C10 C11 C12 -0.6(3) . . . . ?
B1 C10 C11 C12 -175.6(2) . . . . ?
C10 C11 C12 C13 -1.5(4) . . . . ?
C11 C12 C13 C14 1.2(3) . . . . ?
C12 C13 C14 C15 1.0(3) . . . . ?
C13 C14 C15 C10 -3.1(3) . . . . ?
C11 C10 C15 C14 2.8(3) . . . . ?
B1 C10 C15 C14 177.4(2) . . . . ?
C10 B1 C16 C17 120.8(2) . . . . ?
C1 B1 C16 C17 -2.8(3) . . . . ?
N1 B1 C16 C17 -119.6(2) . . . . ?
C10 B1 C16 C21 -48.8(2) . . . . ?
C1 B1 C16 C21 -172.38(18) . . . . ?
N1 B1 C16 C21 70.8(2) . . . . ?
C21 C16 C17 C18 0.2(3) . . . . ?
B1 C16 C17 C18 -169.86(19) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C18 C19 C20 C21 0.7(3) . . . . ?
C19 C20 C21 C16 -0.8(4) . . . . ?
C17 C16 C21 C20 0.4(3) . . . . ?
B1 C16 C21 C20 170.7(2) . . . . ?
C27 N1 C22 C23 -13.3(3) . . . . ?
B1 N1 C22 C23 167.09(18) . . . . ?
C27 N1 C22 P1 163.02(14) . . . . ?
B1 N1 C22 P1 -16.6(2) . . . . ?
C1 P1 C22 N1 11.48(15) . . . . ?
C2 P1 C22 N1 -99.98(14) . . . . ?
C6 P1 C22 N1 126.58(14) . . . . ?
C1 P1 C22 C23 -172.20(17) . . . . ?
C2 P1 C22 C23 76.34(18) . . . . ?
C6 P1 C22 C23 -57.10(19) . . . . ?
N1 C22 C23 C24 -172.31(19) . . . . ?
P1 C22 C23 C24 12.1(2) . . . . ?
N1 C22 C23 C25 -55.3(3) . . . . ?
P1 C22 C23 C25 129.02(18) . . . . ?
N1 C22 C23 C26 67.0(3) . . . . ?
P1 C22 C23 C26 -108.7(2) . . . . ?
C22 N1 C27 C32 99.6(2) . . . . ?
B1 N1 C27 C32 -80.8(2) . . . . ?
C22 N1 C27 C28 -83.8(2) . . . . ?
B1 N1 C27 C28 95.8(2) . . . . ?
C32 C27 C28 C29 -3.7(3) . . . . ?
N1 C27 C28 C29 179.63(19) . . . . ?
C27 C28 C29 C30 0.6(3) . . . . ?
C28 C29 C30 C31 1.7(4) . . . . ?
C29 C30 C31 C32 -1.0(4) . . . . ?
C28 C27 C32 C31 4.3(3) . . . . ?
N1 C27 C32 C31 -179.18(19) . . . . ?
C30 C31 C32 C27 -1.9(3) . . . . ?
O1 S1 C1T F3 -64.9(2) . . . . ?
O3 S1 C1T F3 56.1(2) . . . . ?
O2 S1 C1T F3 176.07(18) . . . . ?
O1 S1 C1T F1 55.8(2) . . . . ?
O3 S1 C1T F1 176.71(17) . . . . ?
O2 S1 C1T F1 -63.30(19) . . . . ?
O1 S1 C1T F2 175.82(19) . . . . ?
O3 S1 C1T F2 -63.2(2) . . . . ?
O2 S1 C1T F2 56.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4A O3 0.98 2.39 3.220(3) 142.2 .
C7 H7C O1 0.98 2.45 3.171(3) 130.5 3_445

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_jcs061_compound_5c
_database_code_depnum_ccdc_archive 'CCDC 1555970'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
4,4-di-tert-butyl-5-methyl-2,2-diphenyl-3,4-dihydro-2H-1,4,2-azaphosphaborol-4-ium-2-uide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H33 B N P'
_chemical_formula_sum            'C23 H33 B N P'
_chemical_formula_weight         365.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4981(5)
_cell_length_b                   18.4460(11)
_cell_length_c                   13.8292(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.972(2)
_cell_angle_gamma                90
_cell_volume                     2151.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9878
_cell_measurement_theta_min      4.0
_cell_measurement_theta_max      72.2

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.150
_shelx_estimated_absorpt_T_min   0.837
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8805
_exptl_absorpt_correction_T_max  0.9424
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   .

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 8+1 runs, 1403 frames, 20/40 sec./frame
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with Photon100 detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            17000
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.014
_diffrn_reflns_theta_max         72.196
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4219
_reflns_number_gt                3682
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       APEX3
_computing_cell_refinement       APEX3
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Shelxtl
_computing_publication_material  publCIF

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0633P)²+0.8057P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4219
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.72718(4) 0.54047(2) 0.27091(2) 0.01664(12) Uani 1 1 d . . . . .
C1 C 0.63377(17) 0.48304(8) 0.35072(10) 0.0188(3) Uani 1 1 d . . . . .
H1A H 0.6935 0.4828 0.4168 0.023 Uiso 1 1 calc R U . . .
H1B H 0.5238 0.4991 0.3553 0.023 Uiso 1 1 calc R U . . .
B1 B 0.63579(18) 0.39985(9) 0.29891(11) 0.0174(3) Uani 1 1 d . . . . .
N1 N 0.74053(14) 0.40525(7) 0.21415(9) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.90562(18) 0.58398(8) 0.33816(11) 0.0209(3) Uani 1 1 d . . . . .
C3 C 0.8631(2) 0.62457(8) 0.42860(11) 0.0264(3) Uani 1 1 d . . . . .
H3A H 0.8102 0.5913 0.4695 0.040 Uiso 1 1 calc R U . . .
H3B H 0.9600 0.6433 0.4658 0.040 Uiso 1 1 calc R U . . .
H3C H 0.7919 0.6650 0.4081 0.040 Uiso 1 1 calc R U . . .
C4 C 1.01989(19) 0.52154(9) 0.36974(12) 0.0280(3) Uani 1 1 d . . . . .
H4A H 0.9688 0.4877 0.4108 0.042 Uiso 1 1 calc R U . . .
H4B H 1.0475 0.4961 0.3119 0.042 Uiso 1 1 calc R U . . .
H4C H 1.1164 0.5410 0.4067 0.042 Uiso 1 1 calc R U . . .
C5 C 0.9884(2) 0.63612(10) 0.27410(13) 0.0335(4) Uani 1 1 d . . . . .
H5A H 0.9169 0.6764 0.2533 0.050 Uiso 1 1 calc R U . . .
H5B H 1.0850 0.6551 0.3114 0.050 Uiso 1 1 calc R U . . .
H5C H 1.0161 0.6102 0.2167 0.050 Uiso 1 1 calc R U . . .
C6 C 0.58008(19) 0.60140(9) 0.20125(11) 0.0256(3) Uani 1 1 d . . . . .
C7 C 0.4489(3) 0.55239(11) 0.15182(18) 0.0534(6) Uani 1 1 d . . . . .
H7A H 0.4938 0.5190 0.1073 0.080 Uiso 1 1 calc R U . . .
H7B H 0.4019 0.5245 0.2014 0.080 Uiso 1 1 calc R U . . .
H7C H 0.3669 0.5822 0.1151 0.080 Uiso 1 1 calc R U . . .
C8 C 0.5095(3) 0.65284(12) 0.27004(15) 0.0502(6) Uani 1 1 d . . . . .
H8A H 0.4654 0.6249 0.3207 0.075 Uiso 1 1 calc R U . . .
H8B H 0.5923 0.6854 0.3004 0.075 Uiso 1 1 calc R U . . .
H8C H 0.4252 0.6815 0.2335 0.075 Uiso 1 1 calc R U . . .
C9 C 0.6487(3) 0.64473(17) 0.1225(2) 0.0692(8) Uani 1 1 d . . . . .
H9A H 0.6943 0.6114 0.0781 0.104 Uiso 1 1 calc R U . . .
H9B H 0.5645 0.6734 0.0858 0.104 Uiso 1 1 calc R U . . .
H9C H 0.7317 0.6773 0.1528 0.104 Uiso 1 1 calc R U . . .
C10 C 0.70488(16) 0.33921(7) 0.37859(10) 0.0178(3) Uani 1 1 d . . . . .
C11 C 0.80373(17) 0.28257(8) 0.35568(11) 0.0208(3) Uani 1 1 d . . . . .
H11 H 0.8424 0.2825 0.2940 0.025 Uiso 1 1 calc R U . . .
C12 C 0.84701(19) 0.22628(8) 0.42081(12) 0.0261(3) Uani 1 1 d . . . . .
H12 H 0.9164 0.1893 0.4036 0.031 Uiso 1 1 calc R U . . .
C13 C 0.78974(19) 0.22373(8) 0.51032(11) 0.0249(3) Uani 1 1 d . . . . .
H13 H 0.8153 0.1842 0.5533 0.030 Uiso 1 1 calc R U . . .
C14 C 0.69492(19) 0.27955(9) 0.53614(11) 0.0257(3) Uani 1 1 d . . . . .
H14 H 0.6563 0.2790 0.5978 0.031 Uiso 1 1 calc R U . . .
C15 C 0.65594(18) 0.33664(8) 0.47167(11) 0.0240(3) Uani 1 1 d . . . . .
H15 H 0.5937 0.3754 0.4917 0.029 Uiso 1 1 calc R U . . .
C16 C 0.45704(17) 0.37495(7) 0.25511(11) 0.0197(3) Uani 1 1 d . . . . .
C17 C 0.41831(19) 0.34971(8) 0.15984(11) 0.0245(3) Uani 1 1 d . . . . .
H17 H 0.4978 0.3487 0.1171 0.029 Uiso 1 1 calc R U . . .
C18 C 0.2653(2) 0.32603(9) 0.12603(12) 0.0315(4) Uani 1 1 d . . . . .
H18 H 0.2422 0.3092 0.0609 0.038 Uiso 1 1 calc R U . . .
C19 C 0.14736(19) 0.32685(9) 0.18670(14) 0.0322(4) Uani 1 1 d . . . . .
H19 H 0.0436 0.3105 0.1636 0.039 Uiso 1 1 calc R U . . .
C20 C 0.18183(19) 0.35169(9) 0.28126(14) 0.0325(4) Uani 1 1 d . . . . .
H20 H 0.1017 0.3525 0.3236 0.039 Uiso 1 1 calc R U . . .
C21 C 0.33392(19) 0.37538(9) 0.31405(13) 0.0286(4) Uani 1 1 d . . . . .
H21 H 0.3555 0.3926 0.3791 0.034 Uiso 1 1 calc R U . . .
C22 C 0.78864(17) 0.46659(8) 0.19096(10) 0.0196(3) Uani 1 1 d . . . . .
C23 C 0.8865(2) 0.48059(9) 0.10857(12) 0.0288(4) Uani 1 1 d . . . . .
H23A H 0.8882 0.4369 0.0684 0.043 Uiso 1 1 calc R U . . .
H23B H 0.9951 0.4933 0.1355 0.043 Uiso 1 1 calc R U . . .
H23C H 0.8397 0.5207 0.0684 0.043 Uiso 1 1 calc R U . . .


_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 1.7842(14) . ?
P1 C6 1.8605(15) . ?
P1 C2 1.8618(15) . ?
P1 C22 1.8689(14) . ?
C1 B1 1.694(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
B1 N1 1.5586(18) . ?
B1 C10 1.629(2) . ?
B1 C16 1.632(2) . ?
N1 C22 1.2579(19) . ?
C2 C5 1.535(2) . ?
C2 C4 1.535(2) . ?
C2 C3 1.538(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C8 1.518(2) . ?
C6 C9 1.523(3) . ?
C6 C7 1.531(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.401(2) . ?
C10 C15 1.401(2) . ?
C11 C12 1.394(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.398(2) . ?
C16 C21 1.402(2) . ?
C17 C18 1.397(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.512(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 C6 110.95(7) . . ?
C1 P1 C2 110.09(7) . . ?
C6 P1 C2 116.97(7) . . ?
C1 P1 C22 96.33(7) . . ?
C6 P1 C22 110.65(7) . . ?
C2 P1 C22 109.92(7) . . ?
B1 C1 P1 104.36(9) . . ?
B1 C1 H1A 110.9 . . ?
P1 C1 H1A 110.9 . . ?
B1 C1 H1B 110.9 . . ?
P1 C1 H1B 110.9 . . ?
H1A C1 H1B 108.9 . . ?
N1 B1 C10 111.14(11) . . ?
N1 B1 C16 109.25(11) . . ?
C10 B1 C16 107.50(11) . . ?
N1 B1 C1 107.23(11) . . ?
C10 B1 C1 110.92(11) . . ?
C16 B1 C1 110.81(11) . . ?
C22 N1 B1 118.82(12) . . ?
C5 C2 C4 108.42(13) . . ?
C5 C2 C3 109.50(13) . . ?
C4 C2 C3 109.69(12) . . ?
C5 C2 P1 112.60(11) . . ?
C4 C2 P1 105.51(10) . . ?
C3 C2 P1 111.01(10) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C6 C9 109.58(19) . . ?
C8 C6 C7 109.10(17) . . ?
C9 C6 C7 108.18(19) . . ?
C8 C6 P1 110.18(11) . . ?
C9 C6 P1 113.30(13) . . ?
C7 C6 P1 106.36(11) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 115.83(13) . . ?
C11 C10 B1 122.42(13) . . ?
C15 C10 B1 121.47(13) . . ?
C12 C11 C10 121.85(14) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C13 C12 C11 120.60(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 119.02(14) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 119.93(14) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 122.65(14) . . ?
C14 C15 H15 118.7 . . ?
C10 C15 H15 118.7 . . ?
C17 C16 C21 116.27(14) . . ?
C17 C16 B1 123.06(13) . . ?
C21 C16 B1 120.62(13) . . ?
C18 C17 C16 121.50(15) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C19 C18 C17 120.46(16) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.42(15) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 119.70(16) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C16 122.65(16) . . ?
C20 C21 H21 118.7 . . ?
C16 C21 H21 118.7 . . ?
N1 C22 C23 124.84(13) . . ?
N1 C22 P1 112.47(11) . . ?
C23 C22 P1 122.69(11) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
C6 P1 C1 B1 108.03(10) . . . . ?
C2 P1 C1 B1 -120.89(9) . . . . ?
C22 P1 C1 B1 -6.95(10) . . . . ?
P1 C1 B1 N1 8.90(13) . . . . ?
P1 C1 B1 C10 130.42(10) . . . . ?
P1 C1 B1 C16 -110.25(11) . . . . ?
C10 B1 N1 C22 -129.05(14) . . . . ?
C16 B1 N1 C22 112.49(14) . . . . ?
C1 B1 N1 C22 -7.66(17) . . . . ?
C1 P1 C2 C5 -178.13(11) . . . . ?
C6 P1 C2 C5 -50.30(14) . . . . ?
C22 P1 C2 C5 76.95(13) . . . . ?
C1 P1 C2 C4 63.79(11) . . . . ?
C6 P1 C2 C4 -168.38(10) . . . . ?
C22 P1 C2 C4 -41.13(12) . . . . ?
C1 P1 C2 C3 -54.96(12) . . . . ?
C6 P1 C2 C3 72.86(12) . . . . ?
C22 P1 C2 C3 -159.88(10) . . . . ?
C1 P1 C6 C8 64.36(15) . . . . ?
C2 P1 C6 C8 -63.05(16) . . . . ?
C22 P1 C6 C8 170.06(14) . . . . ?
C1 P1 C6 C9 -172.48(17) . . . . ?
C2 P1 C6 C9 60.11(18) . . . . ?
C22 P1 C6 C9 -66.78(18) . . . . ?
C1 P1 C6 C7 -53.75(15) . . . . ?
C2 P1 C6 C7 178.84(13) . . . . ?
C22 P1 C6 C7 51.94(15) . . . . ?
N1 B1 C10 C11 -22.26(18) . . . . ?
C16 B1 C10 C11 97.25(15) . . . . ?
C1 B1 C10 C11 -141.46(13) . . . . ?
N1 B1 C10 C15 164.16(13) . . . . ?
C16 B1 C10 C15 -76.33(16) . . . . ?
C1 B1 C10 C15 44.96(17) . . . . ?
C15 C10 C11 C12 1.6(2) . . . . ?
B1 C10 C11 C12 -172.33(13) . . . . ?
C10 C11 C12 C13 1.6(2) . . . . ?
C11 C12 C13 C14 -3.0(2) . . . . ?
C12 C13 C14 C15 1.2(2) . . . . ?
C13 C14 C15 C10 2.2(2) . . . . ?
C11 C10 C15 C14 -3.5(2) . . . . ?
B1 C10 C15 C14 170.51(14) . . . . ?
N1 B1 C16 C17 11.05(19) . . . . ?
C10 B1 C16 C17 -109.66(15) . . . . ?
C1 B1 C16 C17 128.98(14) . . . . ?
N1 B1 C16 C21 -171.43(13) . . . . ?
C10 B1 C16 C21 67.86(17) . . . . ?
C1 B1 C16 C21 -53.51(18) . . . . ?
C21 C16 C17 C18 -0.3(2) . . . . ?
B1 C16 C17 C18 177.32(14) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C17 C18 C19 C20 0.3(2) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C19 C20 C21 C16 -0.4(3) . . . . ?
C17 C16 C21 C20 0.6(2) . . . . ?
B1 C16 C21 C20 -177.11(15) . . . . ?
B1 N1 C22 C23 -178.01(14) . . . . ?
B1 N1 C22 P1 2.47(17) . . . . ?
C1 P1 C22 N1 3.38(12) . . . . ?
C6 P1 C22 N1 -111.85(12) . . . . ?
C2 P1 C22 N1 117.44(12) . . . . ?
C1 P1 C22 C23 -176.16(13) . . . . ?
C6 P1 C22 C23 68.61(14) . . . . ?
C2 P1 C22 C23 -62.09(14) . . . . ?

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_jcs074_compound_7a
_database_code_depnum_ccdc_archive 'CCDC 1555971'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'4,4-di-tert-butyl-1,2,2,5-tetraphenyl-3,4-dihydro-2H-1λ⁴,4,2λ⁴-azaphosphaborol-4-ium trifluoromethanesulfonate dichloromethane solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H40 B N P, C F3 O3 S, C H2 Cl2'
_chemical_formula_sum            'C36 H42 B Cl2 F3 N O3 P S'
_chemical_formula_weight         738.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.0882(5)
_cell_length_b                   17.6065(7)
_cell_length_c                   18.5479(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3621.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9672
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             1544
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.333
_shelx_estimated_absorpt_T_min   0.895
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8961
_exptl_absorpt_correction_T_max  0.9420
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 7+1 runs, 1242 frames, 10 sec./frame
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with Photon100 detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            157311
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.140
_diffrn_reflns_theta_max         27.552
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8349
_reflns_number_gt                7827
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       APEX3
_computing_cell_refinement       APEX3
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    shelxtl
_computing_publication_material  publCIF

_refine_special_details          
;
 One phenyl group, triflate anion and solvent CH2Cl2 disordered.
Use of constraints (EADP) and restraints  (SAME, SADI) in the
refinement. Disordered C-, O- and F-atoms refined isotropically.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)²+5.4513P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3342 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8349
_refine_ls_number_parameters     414
_refine_ls_number_restraints     151
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1350
_refine_ls_wR_factor_gt          0.1299
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.41611(7) 0.56426(4) 0.44060(4) 0.01245(16) Uani 1 1 d . . . . .
C1 C 0.3531(3) 0.58545(19) 0.35470(17) 0.0165(6) Uani 1 1 d . . . . .
H1A H 0.2683 0.5678 0.3528 0.020 Uiso 1 1 calc R U . . .
H1B H 0.3540 0.6410 0.3465 0.020 Uiso 1 1 calc R U . . .
B1 B 0.4335(4) 0.5421(2) 0.29126(19) 0.0175(7) Uani 1 1 d . . . . .
N1 N 0.5468(3) 0.50507(15) 0.33876(15) 0.0167(6) Uani 1 1 d . . . . .
C2 C 0.4632(3) 0.65128(18) 0.48897(18) 0.0174(7) Uani 1 1 d . . . . .
C3 C 0.5301(4) 0.6357(2) 0.5597(2) 0.0240(7) Uani 1 1 d . . . . .
H3A H 0.4775 0.6072 0.5925 0.036 Uiso 1 1 calc R U . . .
H3B H 0.6029 0.6059 0.5498 0.036 Uiso 1 1 calc R U . . .
H3C H 0.5528 0.6840 0.5822 0.036 Uiso 1 1 calc R U . . .
C4 C 0.5473(4) 0.6959(2) 0.4387(2) 0.0256(7) Uani 1 1 d . . . . .
H4A H 0.5056 0.7063 0.3931 0.038 Uiso 1 1 calc R U . . .
H4B H 0.5699 0.7440 0.4616 0.038 Uiso 1 1 calc R U . . .
H4C H 0.6200 0.6659 0.4292 0.038 Uiso 1 1 calc R U . . .
C5 C 0.3480(4) 0.6981(2) 0.5029(2) 0.0270(8) Uani 1 1 d . . . . .
H5A H 0.3065 0.7075 0.4571 0.040 Uiso 1 1 calc R U . . .
H5B H 0.2945 0.6699 0.5353 0.040 Uiso 1 1 calc R U . . .
H5C H 0.3698 0.7467 0.5251 0.040 Uiso 1 1 calc R U . . .
C6 C 0.3221(3) 0.4950(2) 0.49130(18) 0.0185(7) Uani 1 1 d . . . . .
C7 C 0.3326(4) 0.4186(2) 0.4517(2) 0.0239(8) Uani 1 1 d . . . . .
H7A H 0.3095 0.4252 0.4011 0.036 Uiso 1 1 calc R U . . .
H7B H 0.4161 0.4005 0.4543 0.036 Uiso 1 1 calc R U . . .
H7C H 0.2791 0.3814 0.4745 0.036 Uiso 1 1 calc R U . . .
C8 C 0.3579(4) 0.4861(2) 0.57078(19) 0.0249(8) Uani 1 1 d . . . . .
H8A H 0.3506 0.5353 0.5952 0.037 Uiso 1 1 calc R U . . .
H8B H 0.3044 0.4492 0.5940 0.037 Uiso 1 1 calc R U . . .
H8C H 0.4414 0.4683 0.5739 0.037 Uiso 1 1 calc R U . . .
C9 C 0.1890(3) 0.5209(3) 0.4882(2) 0.0306(9) Uani 1 1 d . . . . .
H9A H 0.1644 0.5269 0.4377 0.046 Uiso 1 1 calc R U . . .
H9B H 0.1379 0.4827 0.5115 0.046 Uiso 1 1 calc R U . . .
H9C H 0.1804 0.5696 0.5133 0.046 Uiso 1 1 calc R U . . .
C10 C 0.3617(3) 0.47114(16) 0.25010(16) 0.0308(9) Uani 1 1 d DG . . . .
C11 C 0.4159(3) 0.4270(2) 0.1971(2) 0.0312(13) Uiso 0.585(6) 1 d DG . P A 1
H11 H 0.4954 0.4384 0.1814 0.037 Uiso 0.585(6) 1 calc R U P A 1
C12 C 0.3538(5) 0.3662(2) 0.1671(2) 0.0258(11) Uiso 0.585(6) 1 d DG . P A 1
H12 H 0.3908 0.3360 0.1308 0.031 Uiso 0.585(6) 1 calc R U P A 1
C13 C 0.2374(5) 0.3495(2) 0.1900(2) 0.0232(11) Uiso 0.585(6) 1 d DG . P A 1
H13 H 0.1950 0.3079 0.1695 0.028 Uiso 0.585(6) 1 calc R U P A 1
C14 C 0.1832(3) 0.3936(3) 0.2431(3) 0.0259(11) Uiso 0.585(6) 1 d DG . P A 1
H14 H 0.1037 0.3822 0.2588 0.031 Uiso 0.585(6) 1 calc R U P A 1
C15 C 0.2454(3) 0.4545(2) 0.2731(2) 0.0307(14) Uiso 0.585(6) 1 d DG . P A 1
H15 H 0.2083 0.4846 0.3093 0.037 Uiso 0.585(6) 1 calc R U P A 1
C11A C 0.2501(5) 0.4387(5) 0.2637(5) 0.0312(13) Uiso 0.415(6) 1 d D . P A 2
H11A H 0.1971 0.4609 0.2981 0.037 Uiso 0.415(6) 1 calc R U P A 2
C12A C 0.2165(6) 0.3735(4) 0.2268(5) 0.0258(11) Uiso 0.415(6) 1 d D . P A 2
H12A H 0.1405 0.3506 0.2362 0.031 Uiso 0.415(6) 1 calc R U P A 2
C13A C 0.2935(8) 0.3414(4) 0.1761(4) 0.0232(11) Uiso 0.415(6) 1 d D . P A 2
H13A H 0.2710 0.2958 0.1523 0.028 Uiso 0.415(6) 1 calc R U P A 2
C14A C 0.4031(7) 0.3757(4) 0.1600(4) 0.0259(11) Uiso 0.415(6) 1 d D . P A 2
H14A H 0.4545 0.3548 0.1241 0.031 Uiso 0.415(6) 1 calc R U P A 2
C15A C 0.4368(6) 0.4410(4) 0.1970(4) 0.0307(14) Uiso 0.415(6) 1 d D . P A 2
H15A H 0.5112 0.4652 0.1861 0.037 Uiso 0.415(6) 1 calc R U P A 2
C16 C 0.4873(4) 0.60401(19) 0.23529(18) 0.0209(7) Uani 1 1 d . . . . .
C17 C 0.5884(4) 0.6495(2) 0.24780(19) 0.0262(8) Uani 1 1 d . . . . .
H17 H 0.6319 0.6430 0.2915 0.031 Uiso 1 1 calc R U . . .
C18 C 0.6278(5) 0.7042(2) 0.1987(2) 0.0331(10) Uani 1 1 d . . . . .
H18 H 0.6979 0.7334 0.2085 0.040 Uiso 1 1 calc R U . . .
C19 C 0.5637(5) 0.7155(2) 0.1355(2) 0.0365(11) Uani 1 1 d . . . . .
H19 H 0.5904 0.7520 0.1013 0.044 Uiso 1 1 calc R U . . .
C20 C 0.4605(5) 0.6732(2) 0.1221(2) 0.0354(10) Uani 1 1 d . . . . .
H20 H 0.4150 0.6818 0.0795 0.043 Uiso 1 1 calc R U . . .
C21 C 0.4237(4) 0.6183(2) 0.17129(19) 0.0285(8) Uani 1 1 d . . . . .
H21 H 0.3532 0.5895 0.1612 0.034 Uiso 1 1 calc R U . . .
C22 C 0.5510(3) 0.51322(18) 0.40799(17) 0.0146(6) Uani 1 1 d . . . . .
C23 C 0.6549(3) 0.4912(2) 0.45412(19) 0.0196(7) Uani 1 1 d . . . . .
C24 C 0.6469(4) 0.4385(2) 0.5095(2) 0.0259(8) Uani 1 1 d . . . . .
H24 H 0.5747 0.4102 0.5160 0.031 Uiso 1 1 calc R U . . .
C25 C 0.7438(4) 0.4269(3) 0.5556(3) 0.0417(11) Uani 1 1 d . . . . .
H25 H 0.7386 0.3900 0.5928 0.050 Uiso 1 1 calc R U . . .
C26 C 0.8474(5) 0.4690(3) 0.5472(3) 0.0524(14) Uani 1 1 d . . . . .
H26 H 0.9124 0.4628 0.5801 0.063 Uiso 1 1 calc R U . . .
C27 C 0.8572(4) 0.5202(3) 0.4913(4) 0.0518(15) Uani 1 1 d . . . . .
H27 H 0.9300 0.5479 0.4851 0.062 Uiso 1 1 calc R U . . .
C28 C 0.7616(3) 0.5317(2) 0.4438(3) 0.0327(9) Uani 1 1 d . . . . .
H28 H 0.7689 0.5666 0.4049 0.039 Uiso 1 1 calc R U . . .
C29 C 0.6341(4) 0.4552(2) 0.3036(2) 0.0239(8) Uani 1 1 d . . . . .
C30 C 0.7275(5) 0.4844(3) 0.2622(3) 0.0437(13) Uani 1 1 d . . . . .
H30 H 0.7410 0.5376 0.2592 0.052 Uiso 1 1 calc R U . . .
C31 C 0.8010(6) 0.4331(3) 0.2251(3) 0.0607(19) Uani 1 1 d . . . . .
H31 H 0.8660 0.4515 0.1967 0.073 Uiso 1 1 calc R U . . .
C32 C 0.7806(6) 0.3566(3) 0.2292(3) 0.0560(17) Uani 1 1 d . . . . .
H32 H 0.8302 0.3227 0.2026 0.067 Uiso 1 1 calc R U . . .
C33 C 0.6884(5) 0.3282(3) 0.2717(2) 0.0401(11) Uani 1 1 d . . . . .
H33 H 0.6755 0.2750 0.2749 0.048 Uiso 1 1 calc R U . . .
C34 C 0.6152(4) 0.3779(2) 0.3094(2) 0.0280(9) Uani 1 1 d . . . . .
H34 H 0.5522 0.3590 0.3391 0.034 Uiso 1 1 calc R U . . .
S1 S -0.00507(14) 0.64141(8) 0.34201(8) 0.0220(3) Uiso 0.6148(17) 1 d D . P B 1
O1 O -0.1277(4) 0.6675(3) 0.3534(3) 0.0274(9) Uiso 0.6148(17) 1 d D . P B 1
O2 O 0.0864(5) 0.6886(3) 0.3757(3) 0.0325(10) Uiso 0.6148(17) 1 d D . P B 1
O3 O 0.0146(4) 0.5609(2) 0.3492(2) 0.0292(8) Uiso 0.6148(17) 1 d D . P B 1
C1T C 0.0223(5) 0.6582(3) 0.2460(3) 0.0280(11) Uiso 0.6148(17) 1 d D . P B 1
F1 F -0.0442(5) 0.6141(4) 0.2013(3) 0.0437(9) Uiso 0.6148(17) 1 d D . P B 1
F2 F 0.1366(4) 0.6428(3) 0.2283(3) 0.0403(9) Uiso 0.6148(17) 1 d D . P B 1
F3 F 0.0018(4) 0.7311(2) 0.2296(3) 0.0430(9) Uiso 0.6148(17) 1 d D . P B 1
S1A S -0.0229(2) 0.68003(13) 0.32171(13) 0.0220(3) Uiso 0.3852(17) 1 d D . P B
2
O1A O -0.1489(6) 0.6638(5) 0.3348(5) 0.0274(9) Uiso 0.3852(17) 1 d D . P B 2
O2A O 0.0559(7) 0.6649(5) 0.3827(4) 0.0325(10) Uiso 0.3852(17) 1 d D . P B 2
O3A O 0.0002(7) 0.7484(4) 0.2820(4) 0.0292(8) Uiso 0.3852(17) 1 d D . P B 2
C1TA C 0.0144(7) 0.6042(5) 0.2588(5) 0.0280(11) Uiso 0.3852(17) 1 d D . P B 2
F1A F -0.0678(8) 0.6111(6) 0.2071(5) 0.0437(9) Uiso 0.3852(17) 1 d D . P B 2
F2A F 0.1268(6) 0.6100(5) 0.2340(4) 0.0403(9) Uiso 0.3852(17) 1 d D . P B 2
F3A F 0.0025(7) 0.5361(4) 0.2894(4) 0.0430(9) Uiso 0.3852(17) 1 d D . P B 2
C1C C 0.0476(6) 0.8189(5) 0.0830(6) 0.068(2) Uiso 0.761(6) 1 d D . P C 1
H1C1 H 0.0476 0.8637 0.0508 0.081 Uiso 0.761(6) 1 calc R U P C 1
H1C2 H 0.0539 0.8373 0.1333 0.081 Uiso 0.761(6) 1 calc R U P C 1
Cl1 Cl 0.1715(3) 0.7619(2) 0.0633(2) 0.0511(8) Uani 0.761(6) 1 d D U P C 1
Cl2 Cl -0.08999(18) 0.76821(16) 0.07218(12) 0.0575(7) Uani 0.761(6) 1 d D U P C
1
C1CA C 0.0692(15) 0.8024(15) 0.1253(13) 0.068(2) Uiso 0.239(6) 1 d D . P C 2
H1C3 H 0.0572 0.7791 0.1734 0.081 Uiso 0.239(6) 1 calc R U P C 2
H1C4 H 0.1165 0.8496 0.1319 0.081 Uiso 0.239(6) 1 calc R U P C 2
Cl1A Cl -0.0694(8) 0.8246(9) 0.0886(5) 0.089(3) Uani 0.239(6) 1 d D U P C 2
Cl2A Cl 0.1495(12) 0.7399(7) 0.0707(8) 0.062(3) Uani 0.239(6) 1 d D U P C 2


_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 1.780(3) . ?
P1 C22 1.847(3) . ?
P1 C2 1.851(3) . ?
P1 C6 1.860(3) . ?
C1 B1 1.662(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
B1 C16 1.619(5) . ?
B1 C10 1.667(4) . ?
B1 N1 1.667(5) . ?
N1 C22 1.293(4) . ?
N1 C29 1.461(4) . ?
C2 C3 1.533(5) . ?
C2 C4 1.535(5) . ?
C2 C5 1.542(5) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C8 1.535(5) . ?
C6 C7 1.536(5) . ?
C6 C9 1.545(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11A 1.386(2) . ?
C10 C11 1.3900 . ?
C10 C15 1.3900 . ?
C10 C15A 1.394(2) . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C11A C12A 1.389(2) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.389(2) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.390(2) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.391(2) . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9500 . ?
C16 C17 1.397(6) . ?
C16 C21 1.404(5) . ?
C17 C18 1.395(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.390(6) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.486(5) . ?
C23 C24 1.387(5) . ?
C23 C28 1.395(5) . ?
C24 C25 1.387(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.376(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.378(9) . ?
C26 H26 0.9500 . ?
C27 C28 1.394(7) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C34 1.380(6) . ?
C29 C30 1.387(6) . ?
C30 C31 1.398(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.367(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.384(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.384(6) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
S1 O3 1.440(4) . ?
S1 O1 1.450(5) . ?
S1 O2 1.452(5) . ?
S1 C1T 1.830(6) . ?
C1T F2 1.337(6) . ?
C1T F3 1.338(6) . ?
C1T F1 1.355(7) . ?
S1A O3A 1.434(6) . ?
S1A O1A 1.445(6) . ?
S1A O2A 1.454(6) . ?
S1A C1TA 1.822(9) . ?
C1TA F1A 1.328(8) . ?
C1TA F2A 1.333(8) . ?
C1TA F3A 1.333(8) . ?
C1C Cl1 1.740(8) . ?
C1C Cl2 1.778(8) . ?
C1C H1C1 0.9900 . ?
C1C H1C2 0.9900 . ?
C1CA Cl1A 1.725(12) . ?
C1CA Cl2A 1.741(12) . ?
C1CA H1C3 0.9900 . ?
C1CA H1C4 0.9900 . ?

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 C22 97.29(15) . . ?
C1 P1 C2 111.79(15) . . ?
C22 P1 C2 109.47(16) . . ?
C1 P1 C6 111.71(16) . . ?
C22 P1 C6 107.49(15) . . ?
C2 P1 C6 117.13(16) . . ?
B1 C1 P1 109.1(2) . . ?
B1 C1 H1A 109.9 . . ?
P1 C1 H1A 109.9 . . ?
B1 C1 H1B 109.9 . . ?
P1 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C16 B1 C1 110.0(3) . . ?
C16 B1 C10 112.8(3) . . ?
C1 B1 C10 114.3(3) . . ?
C16 B1 N1 108.9(3) . . ?
C1 B1 N1 102.1(2) . . ?
C10 B1 N1 108.0(3) . . ?
C22 N1 C29 119.1(3) . . ?
C22 N1 B1 120.6(3) . . ?
C29 N1 B1 119.9(3) . . ?
C3 C2 C4 108.5(3) . . ?
C3 C2 C5 110.7(3) . . ?
C4 C2 C5 109.4(3) . . ?
C3 C2 P1 113.8(2) . . ?
C4 C2 P1 107.5(2) . . ?
C5 C2 P1 106.9(3) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C6 C7 110.5(3) . . ?
C8 C6 C9 108.3(3) . . ?
C7 C6 C9 108.3(3) . . ?
C8 C6 P1 114.0(2) . . ?
C7 C6 P1 106.8(2) . . ?
C9 C6 P1 108.8(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 120.0 . . ?
C11A C10 C15A 120.4(3) . . ?
C11A C10 B1 130.7(3) . . ?
C11 C10 B1 122.5(2) . . ?
C15 C10 B1 117.5(2) . . ?
C15A C10 B1 108.8(3) . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.0 . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C10 C11A C12A 119.3(3) . . ?
C10 C11A H11A 120.3 . . ?
C12A C11A H11A 120.3 . . ?
C11A C12A C13A 120.4(3) . . ?
C11A C12A H12A 119.8 . . ?
C13A C12A H12A 119.8 . . ?
C12A C13A C14A 120.4(3) . . ?
C12A C13A H13A 119.8 . . ?
C14A C13A H13A 119.8 . . ?
C13A C14A C15A 119.2(3) . . ?
C13A C14A H14A 120.4 . . ?
C15A C14A H14A 120.4 . . ?
C14A C15A C10 120.2(3) . . ?
C14A C15A H15A 119.9 . . ?
C10 C15A H15A 119.9 . . ?
C17 C16 C21 116.2(3) . . ?
C17 C16 B1 125.1(3) . . ?
C21 C16 B1 118.5(4) . . ?
C18 C17 C16 122.6(4) . . ?
C18 C17 H17 118.7 . . ?
C16 C17 H17 118.7 . . ?
C19 C18 C17 119.4(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 119.8(4) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 119.9(4) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 122.1(4) . . ?
C20 C21 H21 118.9 . . ?
C16 C21 H21 118.9 . . ?
N1 C22 C23 124.8(3) . . ?
N1 C22 P1 110.5(2) . . ?
C23 C22 P1 124.5(2) . . ?
C24 C23 C28 119.9(4) . . ?
C24 C23 C22 123.5(3) . . ?
C28 C23 C22 116.4(3) . . ?
C23 C24 C25 120.3(4) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 119.9(5) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C27 120.2(4) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C28 120.8(5) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C27 C28 C23 118.9(4) . . ?
C27 C28 H28 120.6 . . ?
C23 C28 H28 120.6 . . ?
C34 C29 C30 121.5(4) . . ?
C34 C29 N1 117.2(3) . . ?
C30 C29 N1 121.2(3) . . ?
C29 C30 C31 117.9(4) . . ?
C29 C30 H30 121.1 . . ?
C31 C30 H30 121.1 . . ?
C32 C31 C30 120.9(5) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C31 C32 C33 120.6(4) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C32 C33 C34 119.5(4) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C29 C34 C33 119.6(4) . . ?
C29 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
O3 S1 O1 116.1(3) . . ?
O3 S1 O2 114.7(3) . . ?
O1 S1 O2 114.3(3) . . ?
O3 S1 C1T 103.0(3) . . ?
O1 S1 C1T 104.2(3) . . ?
O2 S1 C1T 102.1(3) . . ?
F2 C1T F3 107.5(5) . . ?
F2 C1T F1 104.4(5) . . ?
F3 C1T F1 108.5(5) . . ?
F2 C1T S1 111.3(4) . . ?
F3 C1T S1 110.4(4) . . ?
F1 C1T S1 114.4(5) . . ?
O3A S1A O1A 115.1(5) . . ?
O3A S1A O2A 116.5(5) . . ?
O1A S1A O2A 114.5(5) . . ?
O3A S1A C1TA 104.2(4) . . ?
O1A S1A C1TA 100.5(4) . . ?
O2A S1A C1TA 103.2(4) . . ?
F1A C1TA F2A 112.7(8) . . ?
F1A C1TA F3A 108.8(8) . . ?
F2A C1TA F3A 108.0(7) . . ?
F1A C1TA S1A 103.8(7) . . ?
F2A C1TA S1A 112.2(6) . . ?
F3A C1TA S1A 111.3(6) . . ?
Cl1 C1C Cl2 111.4(5) . . ?
Cl1 C1C H1C1 109.4 . . ?
Cl2 C1C H1C1 109.4 . . ?
Cl1 C1C H1C2 109.4 . . ?
Cl2 C1C H1C2 109.4 . . ?
H1C1 C1C H1C2 108.0 . . ?
Cl1A C1CA Cl2A 111.7(12) . . ?
Cl1A C1CA H1C3 109.3 . . ?
Cl2A C1CA H1C3 109.3 . . ?
Cl1A C1CA H1C4 109.3 . . ?
Cl2A C1CA H1C4 109.3 . . ?
H1C3 C1CA H1C4 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 P1 C1 B1 6.5(3) . . . . ?
C2 P1 C1 B1 120.9(2) . . . . ?
C6 P1 C1 B1 -105.6(2) . . . . ?
P1 C1 B1 C16 -121.1(3) . . . . ?
P1 C1 B1 C10 110.8(3) . . . . ?
P1 C1 B1 N1 -5.5(3) . . . . ?
C16 B1 N1 C22 118.1(3) . . . . ?
C1 B1 N1 C22 1.8(4) . . . . ?
C10 B1 N1 C22 -119.1(3) . . . . ?
C16 B1 N1 C29 -69.5(4) . . . . ?
C1 B1 N1 C29 174.1(3) . . . . ?
C10 B1 N1 C29 53.3(4) . . . . ?
C1 P1 C2 C3 -173.9(3) . . . . ?
C22 P1 C2 C3 -67.3(3) . . . . ?
C6 P1 C2 C3 55.4(3) . . . . ?
C1 P1 C2 C4 -53.7(3) . . . . ?
C22 P1 C2 C4 52.9(3) . . . . ?
C6 P1 C2 C4 175.6(2) . . . . ?
C1 P1 C2 C5 63.6(3) . . . . ?
C22 P1 C2 C5 170.2(2) . . . . ?
C6 P1 C2 C5 -67.1(3) . . . . ?
C1 P1 C6 C8 -168.8(2) . . . . ?
C22 P1 C6 C8 85.6(3) . . . . ?
C2 P1 C6 C8 -38.0(3) . . . . ?
C1 P1 C6 C7 68.8(3) . . . . ?
C22 P1 C6 C7 -36.8(3) . . . . ?
C2 P1 C6 C7 -160.4(2) . . . . ?
C1 P1 C6 C9 -47.9(3) . . . . ?
C22 P1 C6 C9 -153.5(3) . . . . ?
C2 P1 C6 C9 82.9(3) . . . . ?
C16 B1 C10 C11A -132.3(7) . . . . ?
C1 B1 C10 C11A -5.7(8) . . . . ?
N1 B1 C10 C11A 107.2(8) . . . . ?
C16 B1 C10 C11 55.2(4) . . . . ?
C1 B1 C10 C11 -178.1(3) . . . . ?
N1 B1 C10 C11 -65.2(4) . . . . ?
C16 B1 C10 C15 -127.9(3) . . . . ?
C1 B1 C10 C15 -1.2(4) . . . . ?
N1 B1 C10 C15 111.7(3) . . . . ?
C16 B1 C10 C15A 51.6(6) . . . . ?
C1 B1 C10 C15A 178.3(6) . . . . ?
N1 B1 C10 C15A -68.8(6) . . . . ?
C15 C10 C11 C12 0.0 . . . . ?
B1 C10 C11 C12 176.8(3) . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C10 0.0 . . . . ?
C11 C10 C15 C14 0.0 . . . . ?
B1 C10 C15 C14 -177.0(3) . . . . ?
C15A C10 C11A C12A 3.5(14) . . . . ?
B1 C10 C11A C12A -172.2(6) . . . . ?
C10 C11A C12A C13A -0.6(15) . . . . ?
C11A C12A C13A C14A -2.3(14) . . . . ?
C12A C13A C14A C15A 2.2(14) . . . . ?
C13A C14A C15A C10 0.6(14) . . . . ?
C11A C10 C15A C14A -3.5(13) . . . . ?
B1 C10 C15A C14A 173.1(8) . . . . ?
C1 B1 C16 C17 78.9(4) . . . . ?
C10 B1 C16 C17 -152.1(3) . . . . ?
N1 B1 C16 C17 -32.2(4) . . . . ?
C1 B1 C16 C21 -95.8(4) . . . . ?
C10 B1 C16 C21 33.2(4) . . . . ?
N1 B1 C16 C21 153.1(3) . . . . ?
C21 C16 C17 C18 -2.5(5) . . . . ?
B1 C16 C17 C18 -177.3(3) . . . . ?
C16 C17 C18 C19 1.4(6) . . . . ?
C17 C18 C19 C20 0.9(6) . . . . ?
C18 C19 C20 C21 -1.8(6) . . . . ?
C19 C20 C21 C16 0.5(6) . . . . ?
C17 C16 C21 C20 1.6(5) . . . . ?
B1 C16 C21 C20 176.7(3) . . . . ?
C29 N1 C22 C23 15.7(5) . . . . ?
B1 N1 C22 C23 -171.9(3) . . . . ?
C29 N1 C22 P1 -169.7(2) . . . . ?
B1 N1 C22 P1 2.8(4) . . . . ?
C1 P1 C22 N1 -5.7(3) . . . . ?
C2 P1 C22 N1 -121.9(2) . . . . ?
C6 P1 C22 N1 109.9(3) . . . . ?
C1 P1 C22 C23 169.0(3) . . . . ?
C2 P1 C22 C23 52.8(3) . . . . ?
C6 P1 C22 C23 -75.4(3) . . . . ?
N1 C22 C23 C24 -120.2(4) . . . . ?
P1 C22 C23 C24 65.9(4) . . . . ?
N1 C22 C23 C28 65.7(5) . . . . ?
P1 C22 C23 C28 -108.3(4) . . . . ?
C28 C23 C24 C25 1.2(6) . . . . ?
C22 C23 C24 C25 -172.8(4) . . . . ?
C23 C24 C25 C26 1.4(7) . . . . ?
C24 C25 C26 C27 -2.9(8) . . . . ?
C25 C26 C27 C28 1.9(9) . . . . ?
C26 C27 C28 C23 0.7(8) . . . . ?
C24 C23 C28 C27 -2.2(6) . . . . ?
C22 C23 C28 C27 172.1(4) . . . . ?
C22 N1 C29 C34 76.2(5) . . . . ?
B1 N1 C29 C34 -96.3(4) . . . . ?
C22 N1 C29 C30 -107.9(5) . . . . ?
B1 N1 C29 C30 79.6(5) . . . . ?
C34 C29 C30 C31 1.3(8) . . . . ?
N1 C29 C30 C31 -174.5(5) . . . . ?
C29 C30 C31 C32 0.5(10) . . . . ?
C30 C31 C32 C33 -1.6(11) . . . . ?
C31 C32 C33 C34 1.0(9) . . . . ?
C30 C29 C34 C33 -1.9(7) . . . . ?
N1 C29 C34 C33 174.0(4) . . . . ?
C32 C33 C34 C29 0.7(7) . . . . ?
O3 S1 C1T F2 -63.7(5) . . . . ?
O1 S1 C1T F2 174.7(4) . . . . ?
O2 S1 C1T F2 55.5(5) . . . . ?
O3 S1 C1T F3 177.1(4) . . . . ?
O1 S1 C1T F3 55.5(5) . . . . ?
O2 S1 C1T F3 -63.7(5) . . . . ?
O3 S1 C1T F1 54.3(5) . . . . ?
O1 S1 C1T F1 -67.3(5) . . . . ?
O2 S1 C1T F1 173.5(5) . . . . ?
O3A S1A C1TA F1A -65.9(7) . . . . ?
O1A S1A C1TA F1A 53.5(7) . . . . ?
O2A S1A C1TA F1A 172.0(7) . . . . ?
O3A S1A C1TA F2A 56.0(7) . . . . ?
O1A S1A C1TA F2A 175.5(6) . . . . ?
O2A S1A C1TA F2A -66.0(7) . . . . ?
O3A S1A C1TA F3A 177.2(6) . . . . ?
O1A S1A C1TA F3A -63.4(7) . . . . ?
O2A S1A C1TA F3A 55.1(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3C O2 0.98 2.40 3.376(6) 171.0 4_566
C7 H7C Cl1A 0.98 2.79 3.438(8) 124.4 3_545
C7 H7C Cl2A 0.98 2.89 3.563(14) 126.4 2_565
C9 H9A O3 0.98 2.41 3.298(6) 150.3 .
C1CA H1C3 O3A 0.99 2.18 3.15(3) 166.8 .

_refine_diff_density_max         0.947
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.071


# start Validation Reply Form
_vrf_PLAT201_jcs074_compound_7a  
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          5 Report
RESPONSE: phenyl group disordered, disordered C-atoms refined isotropically.
;
_vrf_PLAT410_jcs074_compound_7a  
;
PROBLEM: Short Intra H...H Contact  H1A    ..  H15     ..       1.80 Ang.  
RESPONSE: due to steric bulkiness (CH2 in the 5-membered ring vs. 
disordered phenyl-ring bonded at B1)
;
####################################################################### 
# 
# 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_jcs060_compound_5a
_database_code_depnum_ccdc_archive 'CCDC 1555969'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
4,4-di-tert-butyl-5-methyl-2,2-diphenyl-3,4-dihydro-2H-1,4,2-azaphosphaborol-4-ium-2-uide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H35 B N P'
_chemical_formula_sum            'C28 H35 B N P'
_chemical_formula_weight         427.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1447(2)
_cell_length_b                   16.6623(4)
_cell_length_c                   17.5476(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.644(1)
_cell_angle_gamma                90
_cell_volume                     2380.4(1)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9881
_cell_measurement_theta_min      5.5
_cell_measurement_theta_max      72.0

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.115
_shelx_estimated_absorpt_T_min   0.825
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8423
_exptl_absorpt_correction_T_max  0.9154
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   .

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 12+1 runs, 1873 frames, 12/18/24 sec./frame
;


_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with Photon100 detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            27593
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.659
_diffrn_reflns_theta_max         72.078
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4666
_reflns_number_gt                4261
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       APEX3
_computing_cell_refinement       APEX3
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Shelxtl
_computing_publication_material  publCIF

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²+1.2023P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00071(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4666
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.61156(12) 0.26089(6) 0.62984(6) 0.0156(2) Uani 1 1 d . . . . .
B1 B 0.50830(17) 0.33341(9) 0.59969(8) 0.0165(3) Uani 1 1 d . . . . .
C1 C 0.49041(16) 0.32177(8) 0.50440(7) 0.0193(3) Uani 1 1 d . . . . .
H1A H 0.5312 0.3700 0.4780 0.023 Uiso 1 1 calc R U . . .
H1B H 0.3741 0.3130 0.4886 0.023 Uiso 1 1 calc R U . . .
P1 P 0.61076(4) 0.23660(2) 0.48180(2) 0.01577(10) Uani 1 1 d . . . . .
C2 C 0.78803(17) 0.26739(9) 0.42286(8) 0.0235(3) Uani 1 1 d . . . . .
C3 C 0.87116(19) 0.19784(10) 0.38186(9) 0.0312(3) Uani 1 1 d . . . . .
H3A H 0.7918 0.1723 0.3465 0.047 Uiso 1 1 calc R U . . .
H3B H 0.9640 0.2184 0.3534 0.047 Uiso 1 1 calc R U . . .
H3C H 0.9108 0.1583 0.4195 0.047 Uiso 1 1 calc R U . . .
C4 C 0.91156(18) 0.30780(10) 0.47846(9) 0.0303(3) Uani 1 1 d . . . . .
H4A H 0.8577 0.3522 0.5045 0.046 Uiso 1 1 calc R U . . .
H4B H 0.9513 0.2685 0.5162 0.046 Uiso 1 1 calc R U . . .
H4C H 1.0045 0.3285 0.4501 0.046 Uiso 1 1 calc R U . . .
C5 C 0.7313(2) 0.32869(11) 0.36202(10) 0.0391(4) Uani 1 1 d . . . . .
H5A H 0.6775 0.3740 0.3867 0.059 Uiso 1 1 calc R U . . .
H5B H 0.8267 0.3481 0.3346 0.059 Uiso 1 1 calc R U . . .
H5C H 0.6537 0.3030 0.3260 0.059 Uiso 1 1 calc R U . . .
C6 C 0.47576(17) 0.15710(8) 0.43963(8) 0.0221(3) Uani 1 1 d . . . . .
C7 C 0.56718(19) 0.07793(9) 0.42624(9) 0.0281(3) Uani 1 1 d . . . . .
H7A H 0.6165 0.0590 0.4745 0.042 Uiso 1 1 calc R U . . .
H7B H 0.4897 0.0376 0.4062 0.042 Uiso 1 1 calc R U . . .
H7C H 0.6537 0.0867 0.3894 0.042 Uiso 1 1 calc R U . . .
C8 C 0.34041(18) 0.14097(9) 0.49724(9) 0.0299(3) Uani 1 1 d . . . . .
H8A H 0.2803 0.1908 0.5067 0.045 Uiso 1 1 calc R U . . .
H8B H 0.2643 0.1004 0.4765 0.045 Uiso 1 1 calc R U . . .
H8C H 0.3905 0.1215 0.5452 0.045 Uiso 1 1 calc R U . . .
C9 C 0.39739(19) 0.18788(9) 0.36440(9) 0.0299(3) Uani 1 1 d . . . . .
H9A H 0.3395 0.2384 0.3737 0.045 Uiso 1 1 calc R U . . .
H9B H 0.4834 0.1970 0.3274 0.045 Uiso 1 1 calc R U . . .
H9C H 0.3194 0.1479 0.3442 0.045 Uiso 1 1 calc R U . . .
C10 C 0.59847(15) 0.41730(8) 0.62478(8) 0.0185(3) Uani 1 1 d . . . . .
C11 C 0.66450(17) 0.47291(8) 0.57471(9) 0.0242(3) Uani 1 1 d . . . . .
H11 H 0.6577 0.4622 0.5215 0.029 Uiso 1 1 calc R U . . .
C12 C 0.74000(18) 0.54344(9) 0.59978(10) 0.0310(4) Uani 1 1 d . . . . .
H12 H 0.7848 0.5793 0.5638 0.037 Uiso 1 1 calc R U . . .
C13 C 0.75039(19) 0.56165(9) 0.67628(10) 0.0340(4) Uani 1 1 d . . . . .
H13 H 0.8014 0.6099 0.6933 0.041 Uiso 1 1 calc R U . . .
C14 C 0.68505(19) 0.50830(10) 0.72810(10) 0.0320(3) Uani 1 1 d . . . . .
H14 H 0.6908 0.5200 0.7811 0.038 Uiso 1 1 calc R U . . .
C15 C 0.61118(17) 0.43770(9) 0.70237(8) 0.0240(3) Uani 1 1 d . . . . .
H15 H 0.5676 0.4019 0.7387 0.029 Uiso 1 1 calc R U . . .
C16 C 0.32635(15) 0.32749(8) 0.63520(7) 0.0175(3) Uani 1 1 d . . . . .
C17 C 0.26603(17) 0.25810(8) 0.66928(8) 0.0221(3) Uani 1 1 d . . . . .
H17 H 0.3369 0.2132 0.6760 0.026 Uiso 1 1 calc R U . . .
C18 C 0.10489(18) 0.25269(9) 0.69373(8) 0.0263(3) Uani 1 1 d . . . . .
H18 H 0.0671 0.2043 0.7159 0.032 Uiso 1 1 calc R U . . .
C19 C 0.00008(17) 0.31762(10) 0.68571(8) 0.0266(3) Uani 1 1 d . . . . .
H19 H -0.1096 0.3141 0.7024 0.032 Uiso 1 1 calc R U . . .
C20 C 0.05640(17) 0.38764(9) 0.65321(8) 0.0265(3) Uani 1 1 d . . . . .
H20 H -0.0145 0.4327 0.6478 0.032 Uiso 1 1 calc R U . . .
C21 C 0.21678(16) 0.39223(8) 0.62843(8) 0.0222(3) Uani 1 1 d . . . . .
H21 H 0.2533 0.4408 0.6062 0.027 Uiso 1 1 calc R U . . .
C22 C 0.66889(15) 0.21089(8) 0.58356(7) 0.0167(3) Uani 1 1 d . . . . .
C23 C 0.75531(15) 0.13630(8) 0.60929(7) 0.0168(3) Uani 1 1 d . . . . .
C24 C 0.89400(18) 0.10540(9) 0.57508(8) 0.0254(3) Uani 1 1 d . . . . .
H24 H 0.9354 0.1309 0.5311 0.030 Uiso 1 1 calc R U . . .
C25 C 0.97234(18) 0.03774(9) 0.60458(9) 0.0278(3) Uani 1 1 d . . . . .
H25 H 1.0676 0.0177 0.5811 0.033 Uiso 1 1 calc R U . . .
C26 C 0.91290(18) -0.00064(8) 0.66783(8) 0.0245(3) Uani 1 1 d . . . . .
H26 H 0.9669 -0.0469 0.6879 0.029 Uiso 1 1 calc R U . . .
C27 C 0.77351(18) 0.02900(8) 0.70181(8) 0.0241(3) Uani 1 1 d . . . . .
H27 H 0.7311 0.0026 0.7450 0.029 Uiso 1 1 calc R U . . .
C28 C 0.69602(16) 0.09704(8) 0.67293(7) 0.0194(3) Uani 1 1 d . . . . .
H28 H 0.6013 0.1171 0.6969 0.023 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C22 1.2623(17) . ?
N1 B1 1.5561(17) . ?
B1 C16 1.6270(19) . ?
B1 C10 1.6336(19) . ?
B1 C1 1.6856(19) . ?
C1 P1 1.7760(13) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
P1 C6 1.8613(14) . ?
P1 C2 1.8717(14) . ?
P1 C22 1.8835(13) . ?
C2 C3 1.532(2) . ?
C2 C4 1.537(2) . ?
C2 C5 1.539(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.5361(19) . ?
C6 C9 1.5379(19) . ?
C6 C8 1.541(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.3953(19) . ?
C10 C15 1.4042(19) . ?
C11 C12 1.392(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.3973(19) . ?
C16 C21 1.4029(18) . ?
C17 C18 1.3953(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.391(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.4918(17) . ?
C23 C28 1.3925(18) . ?
C23 C24 1.3930(19) . ?
C24 C25 1.388(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.381(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.388(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.3864(19) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 N1 B1 120.01(11) . . ?
N1 B1 C16 108.18(10) . . ?
N1 B1 C10 109.78(10) . . ?
C16 B1 C10 110.86(10) . . ?
N1 B1 C1 106.16(10) . . ?
C16 B1 C1 108.61(10) . . ?
C10 B1 C1 113.03(11) . . ?
B1 C1 P1 106.31(8) . . ?
B1 C1 H1A 110.5 . . ?
P1 C1 H1A 110.5 . . ?
B1 C1 H1B 110.5 . . ?
P1 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
C1 P1 C6 109.50(6) . . ?
C1 P1 C2 110.11(6) . . ?
C6 P1 C2 115.58(6) . . ?
C1 P1 C22 95.47(6) . . ?
C6 P1 C22 110.15(6) . . ?
C2 P1 C22 114.16(6) . . ?
C3 C2 C4 109.84(12) . . ?
C3 C2 C5 107.71(13) . . ?
C4 C2 C5 109.13(13) . . ?
C3 C2 P1 114.23(10) . . ?
C4 C2 P1 105.71(9) . . ?
C5 C2 P1 110.14(10) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C9 110.25(12) . . ?
C7 C6 C8 108.04(12) . . ?
C9 C6 C8 109.53(12) . . ?
C7 C6 P1 112.86(10) . . ?
C9 C6 P1 109.26(10) . . ?
C8 C6 P1 106.80(10) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 115.51(13) . . ?
C11 C10 B1 125.24(12) . . ?
C15 C10 B1 119.24(12) . . ?
C12 C11 C10 122.45(14) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C13 C12 C11 120.57(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 118.91(14) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 C15 119.96(15) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 122.60(14) . . ?
C14 C15 H15 118.7 . . ?
C10 C15 H15 118.7 . . ?
C17 C16 C21 116.22(12) . . ?
C17 C16 B1 123.32(11) . . ?
C21 C16 B1 120.34(12) . . ?
C18 C17 C16 122.03(13) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C19 C18 C17 120.11(14) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.40(13) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C19 C20 C21 120.08(13) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 122.15(14) . . ?
C20 C21 H21 118.9 . . ?
C16 C21 H21 118.9 . . ?
N1 C22 C23 122.35(11) . . ?
N1 C22 P1 111.85(9) . . ?
C23 C22 P1 125.45(9) . . ?
C28 C23 C24 118.43(12) . . ?
C28 C23 C22 117.56(11) . . ?
C24 C23 C22 123.98(12) . . ?
C25 C24 C23 120.61(13) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C26 C25 C24 120.53(13) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 119.38(13) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C28 C27 C26 120.21(13) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C23 120.84(12) . . ?
C27 C28 H28 119.6 . . ?
C23 C28 H28 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
C22 N1 B1 C16 119.74(12) . . . . ?
C22 N1 B1 C10 -119.17(13) . . . . ?
C22 N1 B1 C1 3.32(15) . . . . ?
N1 B1 C1 P1 -4.40(12) . . . . ?
C16 B1 C1 P1 -120.53(10) . . . . ?
C10 B1 C1 P1 116.01(10) . . . . ?
B1 C1 P1 C6 117.36(9) . . . . ?
B1 C1 P1 C2 -114.51(9) . . . . ?
B1 C1 P1 C22 3.71(9) . . . . ?
C1 P1 C2 C3 -163.82(10) . . . . ?
C6 P1 C2 C3 -39.11(13) . . . . ?
C22 P1 C2 C3 90.19(11) . . . . ?
C1 P1 C2 C4 75.30(11) . . . . ?
C6 P1 C2 C4 -159.99(9) . . . . ?
C22 P1 C2 C4 -30.70(12) . . . . ?
C1 P1 C2 C5 -42.46(13) . . . . ?
C6 P1 C2 C5 82.24(12) . . . . ?
C22 P1 C2 C5 -148.46(11) . . . . ?
C1 P1 C6 C7 -173.89(10) . . . . ?
C2 P1 C6 C7 61.08(12) . . . . ?
C22 P1 C6 C7 -70.14(11) . . . . ?
C1 P1 C6 C9 63.07(11) . . . . ?
C2 P1 C6 C9 -61.95(12) . . . . ?
C22 P1 C6 C9 166.83(9) . . . . ?
C1 P1 C6 C8 -55.32(11) . . . . ?
C2 P1 C6 C8 179.66(9) . . . . ?
C22 P1 C6 C8 48.44(11) . . . . ?
N1 B1 C10 C11 114.62(14) . . . . ?
C16 B1 C10 C11 -125.91(13) . . . . ?
C1 B1 C10 C11 -3.70(17) . . . . ?
N1 B1 C10 C15 -66.23(15) . . . . ?
C16 B1 C10 C15 53.24(15) . . . . ?
C1 B1 C10 C15 175.46(11) . . . . ?
C15 C10 C11 C12 0.8(2) . . . . ?
B1 C10 C11 C12 -179.97(13) . . . . ?
C10 C11 C12 C13 -0.9(2) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C13 C14 C15 C10 -0.2(2) . . . . ?
C11 C10 C15 C14 -0.3(2) . . . . ?
B1 C10 C15 C14 -179.51(13) . . . . ?
N1 B1 C16 C17 -15.19(17) . . . . ?
C10 B1 C16 C17 -135.61(13) . . . . ?
C1 B1 C16 C17 99.64(14) . . . . ?
N1 B1 C16 C21 168.86(11) . . . . ?
C10 B1 C16 C21 48.44(16) . . . . ?
C1 B1 C16 C21 -76.32(14) . . . . ?
C21 C16 C17 C18 1.4(2) . . . . ?
B1 C16 C17 C18 -174.74(13) . . . . ?
C16 C17 C18 C19 -1.1(2) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
C18 C19 C20 C21 0.4(2) . . . . ?
C19 C20 C21 C16 -0.1(2) . . . . ?
C17 C16 C21 C20 -0.81(19) . . . . ?
B1 C16 C21 C20 175.42(12) . . . . ?
B1 N1 C22 C23 -174.21(11) . . . . ?
B1 N1 C22 P1 -0.60(15) . . . . ?
C1 P1 C22 N1 -2.17(11) . . . . ?
C6 P1 C22 N1 -115.27(10) . . . . ?
C2 P1 C22 N1 112.76(10) . . . . ?
C1 P1 C22 C23 171.20(11) . . . . ?
C6 P1 C22 C23 58.09(12) . . . . ?
C2 P1 C22 C23 -73.87(12) . . . . ?
N1 C22 C23 C28 37.19(18) . . . . ?
P1 C22 C23 C28 -135.52(11) . . . . ?
N1 C22 C23 C24 -140.65(14) . . . . ?
P1 C22 C23 C24 46.64(18) . . . . ?
C28 C23 C24 C25 -0.9(2) . . . . ?
C22 C23 C24 C25 176.88(13) . . . . ?
C23 C24 C25 C26 0.8(2) . . . . ?
C24 C25 C26 C27 0.1(2) . . . . ?
C25 C26 C27 C28 -0.7(2) . . . . ?
C26 C27 C28 C23 0.6(2) . . . . ?
C24 C23 C28 C27 0.3(2) . . . . ?
C22 C23 C28 C27 -177.68(12) . . . . ?

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_jcs066_compound_4
_database_code_depnum_ccdc_archive 'CCDC 1555968'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ((di-tert-butylphosphonio)methyl)triphenylborate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H36 B P'
_chemical_formula_sum            'C27 H36 B P'
_chemical_formula_weight         402.34

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.3762(6)
_cell_length_b                   15.4227(5)
_cell_length_c                   17.5727(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4709.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9633
_cell_measurement_theta_min      4.5
_cell_measurement_theta_max      71.2

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.083
_shelx_estimated_absorpt_T_min   0.781
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8216
_exptl_absorpt_correction_T_max  0.9154
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1.8 deg., 10+1 runs, 1192 frames, 18/24/30/36 sec./frame
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with Photon100 detector'
_diffrn_measurement_method       'rotation in φ and ω, 1.8°, shutterless'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            53352
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.585
_diffrn_reflns_theta_max         72.225
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4637
_reflns_number_gt                4137
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       APEX3
_computing_cell_refinement       APEX3
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Shelxtl
_computing_publication_material  publCIF
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+2.8303P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4637
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.66644(2) 0.23501(2) 0.19645(2) 0.01910(11) Uani 1 1 d . . . . .
H1 H 0.6205(10) 0.2853(11) 0.1574(10) 0.025(4) Uiso 1 1 d . . . . .
B1 B 0.62150(9) 0.35156(10) 0.32912(9) 0.0205(3) Uani 1 1 d . . . . .
C1 C 0.66677(11) 0.26215(12) 0.29492(9) 0.0382(4) Uani 1 1 d . . . . .
H1A H 0.6451 0.2117 0.3224 0.046 Uiso 1 1 calc R U . . .
H1B H 0.7214 0.2667 0.3105 0.046 Uiso 1 1 calc R U . . .
C2 C 0.62584(8) 0.12547(9) 0.18339(9) 0.0241(3) Uani 1 1 d . . . . .
C3 C 0.66619(10) 0.05941(10) 0.23495(11) 0.0351(4) Uani 1 1 d . . . . .
H3A H 0.6632 0.0789 0.2879 0.053 Uiso 1 1 calc R U . . .
H3B H 0.6409 0.0029 0.2300 0.053 Uiso 1 1 calc R U . . .
H3C H 0.7203 0.0542 0.2198 0.053 Uiso 1 1 calc R U . . .
C4 C 0.54083(9) 0.13348(11) 0.20730(11) 0.0367(4) Uani 1 1 d . . . . .
H4A H 0.5379 0.1522 0.2605 0.055 Uiso 1 1 calc R U . . .
H4B H 0.5151 0.1763 0.1749 0.055 Uiso 1 1 calc R U . . .
H4C H 0.5154 0.0771 0.2017 0.055 Uiso 1 1 calc R U . . .
C5 C 0.62982(10) 0.09623(11) 0.10016(10) 0.0348(4) Uani 1 1 d . . . . .
H5A H 0.6038 0.1390 0.0679 0.052 Uiso 1 1 calc R U . . .
H5B H 0.6838 0.0911 0.0846 0.052 Uiso 1 1 calc R U . . .
H5C H 0.6044 0.0399 0.0948 0.052 Uiso 1 1 calc R U . . .
C6 C 0.75994(9) 0.25727(10) 0.15108(10) 0.0318(4) Uani 1 1 d . . . . .
C7 C 0.78414(11) 0.34869(12) 0.17590(15) 0.0541(6) Uani 1 1 d . . . . .
H7A H 0.7444 0.3904 0.1609 0.081 Uiso 1 1 calc R U . . .
H7B H 0.7905 0.3501 0.2313 0.081 Uiso 1 1 calc R U . . .
H7C H 0.8329 0.3640 0.1514 0.081 Uiso 1 1 calc R U . . .
C8 C 0.82057(11) 0.19212(14) 0.17380(16) 0.0566(6) Uani 1 1 d . . . . .
H8A H 0.8045 0.1340 0.1577 0.085 Uiso 1 1 calc R U . . .
H8B H 0.8695 0.2070 0.1493 0.085 Uiso 1 1 calc R U . . .
H8C H 0.8271 0.1931 0.2292 0.085 Uiso 1 1 calc R U . . .
C9 C 0.74932(14) 0.25838(16) 0.06421(12) 0.0570(6) Uani 1 1 d . . . . .
H9A H 0.7098 0.3010 0.0506 0.085 Uiso 1 1 calc R U . . .
H9B H 0.7981 0.2741 0.0398 0.085 Uiso 1 1 calc R U . . .
H9C H 0.7333 0.2008 0.0468 0.085 Uiso 1 1 calc R U . . .
C10 C 0.57338(8) 0.39781(9) 0.25992(8) 0.0201(3) Uani 1 1 d . . . . .
C11 C 0.49908(8) 0.36954(9) 0.24037(8) 0.0221(3) Uani 1 1 d . . . . .
H11 H 0.4749 0.3270 0.2714 0.027 Uiso 1 1 calc R U . . .
C12 C 0.45942(8) 0.40124(10) 0.17750(8) 0.0258(3) Uani 1 1 d . . . . .
H12 H 0.4095 0.3798 0.1661 0.031 Uiso 1 1 calc R U . . .
C13 C 0.49255(9) 0.46395(10) 0.13144(9) 0.0283(3) Uani 1 1 d . . . . .
H13 H 0.4655 0.4863 0.0888 0.034 Uiso 1 1 calc R U . . .
C14 C 0.56572(9) 0.49354(10) 0.14863(9) 0.0286(3) Uani 1 1 d . . . . .
H14 H 0.5894 0.5361 0.1173 0.034 Uiso 1 1 calc R U . . .
C15 C 0.60478(9) 0.46109(9) 0.21177(8) 0.0238(3) Uani 1 1 d . . . . .
H15 H 0.6548 0.4827 0.2226 0.029 Uiso 1 1 calc R U . . .
C16 C 0.68425(8) 0.41632(10) 0.36991(8) 0.0236(3) Uani 1 1 d . . . . .
C17 C 0.67185(9) 0.50571(11) 0.37763(9) 0.0302(3) Uani 1 1 d . . . . .
H17 H 0.6279 0.5307 0.3542 0.036 Uiso 1 1 calc R U . . .
C18 C 0.72169(10) 0.55936(12) 0.41848(10) 0.0385(4) Uani 1 1 d . . . . .
H18 H 0.7115 0.6198 0.4219 0.046 Uiso 1 1 calc R U . . .
C19 C 0.78576(10) 0.52499(13) 0.45393(10) 0.0416(4) Uani 1 1 d . . . . .
H19 H 0.8197 0.5613 0.4819 0.050 Uiso 1 1 calc R U . . .
C20 C 0.79976(10) 0.43751(13) 0.44825(9) 0.0377(4) Uani 1 1 d . . . . .
H20 H 0.8435 0.4130 0.4726 0.045 Uiso 1 1 calc R U . . .
C21 C 0.75009(9) 0.38487(11) 0.40697(8) 0.0296(3) Uani 1 1 d . . . . .
H21 H 0.7612 0.3247 0.4037 0.036 Uiso 1 1 calc R U . . .
C22 C 0.56215(8) 0.32208(10) 0.39728(8) 0.0231(3) Uani 1 1 d . . . . .
C23 C 0.50891(8) 0.38259(11) 0.42503(8) 0.0271(3) Uani 1 1 d . . . . .
H23 H 0.5080 0.4387 0.4028 0.033 Uiso 1 1 calc R U . . .
C24 C 0.45746(9) 0.36469(13) 0.48330(9) 0.0364(4) Uani 1 1 d . . . . .
H24 H 0.4223 0.4079 0.4999 0.044 Uiso 1 1 calc R U . . .
C25 C 0.45751(10) 0.28376(15) 0.51712(10) 0.0439(5) Uani 1 1 d . . . . .
H25 H 0.4221 0.2706 0.5567 0.053 Uiso 1 1 calc R U . . .
C26 C 0.50938(12) 0.22266(13) 0.49271(12) 0.0472(5) Uani 1 1 d . . . . .
H26 H 0.5104 0.1671 0.5160 0.057 Uiso 1 1 calc R U . . .
C27 C 0.56070(10) 0.24156(11) 0.43378(10) 0.0364(4) Uani 1 1 d . . . . .
H27 H 0.5959 0.1981 0.4179 0.044 Uiso 1 1 calc R U . . .


_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 1.7804(16) . ?
P1 C6 1.8420(16) . ?
P1 C2 1.8451(15) . ?
P1 H1 1.307(17) . ?
B1 C10 1.639(2) . ?
B1 C16 1.643(2) . ?
B1 C22 1.645(2) . ?
B1 C1 1.697(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C5 1.532(2) . ?
C2 C3 1.533(2) . ?
C2 C4 1.541(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C8 1.510(2) . ?
C6 C7 1.535(2) . ?
C6 C9 1.538(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.402(2) . ?
C10 C11 1.405(2) . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.402(2) . ?
C16 C21 1.403(2) . ?
C17 C18 1.396(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.375(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C27 1.398(2) . ?
C22 C23 1.402(2) . ?
C23 C24 1.387(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.373(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.397(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 C6 111.96(9) . . ?
C1 P1 C2 109.72(8) . . ?
C6 P1 C2 117.01(7) . . ?
C1 P1 H1 111.8(7) . . ?
C6 P1 H1 101.6(7) . . ?
C2 P1 H1 104.2(7) . . ?
C10 B1 C16 113.43(12) . . ?
C10 B1 C22 109.92(11) . . ?
C16 B1 C22 105.45(11) . . ?
C10 B1 C1 109.11(11) . . ?
C16 B1 C1 109.92(12) . . ?
C22 B1 C1 108.90(12) . . ?
B1 C1 P1 122.25(11) . . ?
B1 C1 H1A 106.8 . . ?
P1 C1 H1A 106.8 . . ?
B1 C1 H1B 106.8 . . ?
P1 C1 H1B 106.8 . . ?
H1A C1 H1B 106.6 . . ?
C5 C2 C3 110.36(13) . . ?
C5 C2 C4 109.10(13) . . ?
C3 C2 C4 109.30(13) . . ?
C5 C2 P1 111.77(10) . . ?
C3 C2 P1 111.11(11) . . ?
C4 C2 P1 105.02(10) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C6 C7 110.19(16) . . ?
C8 C6 C9 110.71(17) . . ?
C7 C6 C9 107.74(17) . . ?
C8 C6 P1 112.15(13) . . ?
C7 C6 P1 106.86(12) . . ?
C9 C6 P1 109.01(12) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 115.21(13) . . ?
C15 C10 B1 123.50(13) . . ?
C11 C10 B1 121.00(12) . . ?
C12 C11 C10 122.71(14) . . ?
C12 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
C13 C12 C11 120.21(14) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 118.95(14) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 120.18(14) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 122.74(14) . . ?
C14 C15 H15 118.6 . . ?
C10 C15 H15 118.6 . . ?
C17 C16 C21 114.85(14) . . ?
C17 C16 B1 122.55(13) . . ?
C21 C16 B1 122.24(14) . . ?
C18 C17 C16 122.49(16) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C19 C18 C17 120.28(17) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 119.11(16) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 120.10(17) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 123.16(17) . . ?
C20 C21 H21 118.4 . . ?
C16 C21 H21 118.4 . . ?
C27 C22 C23 114.83(14) . . ?
C27 C22 B1 126.23(14) . . ?
C23 C22 B1 118.90(13) . . ?
C24 C23 C22 123.35(16) . . ?
C24 C23 H23 118.3 . . ?
C22 C23 H23 118.3 . . ?
C25 C24 C23 119.78(17) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C26 C25 C24 119.07(16) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C25 C26 C27 120.49(17) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C22 122.47(17) . . ?
C26 C27 H27 118.8 . . ?
C22 C27 H27 118.8 . . ?

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 B1 C1 P1 5.8(2) . . . . ?
C16 B1 C1 P1 -119.14(15) . . . . ?
C22 B1 C1 P1 125.80(14) . . . . ?
C6 P1 C1 B1 105.61(15) . . . . ?
C2 P1 C1 B1 -122.74(14) . . . . ?
C1 P1 C2 C5 -175.73(11) . . . . ?
C6 P1 C2 C5 -46.79(14) . . . . ?
C1 P1 C2 C3 -51.96(13) . . . . ?
C6 P1 C2 C3 76.98(13) . . . . ?
C1 P1 C2 C4 66.10(12) . . . . ?
C6 P1 C2 C4 -164.96(11) . . . . ?
C1 P1 C6 C8 73.51(16) . . . . ?
C2 P1 C6 C8 -54.35(17) . . . . ?
C1 P1 C6 C7 -47.34(16) . . . . ?
C2 P1 C6 C7 -175.20(13) . . . . ?
C1 P1 C6 C9 -163.51(13) . . . . ?
C2 P1 C6 C9 68.62(15) . . . . ?
C16 B1 C10 C15 33.56(18) . . . . ?
C22 B1 C10 C15 151.32(13) . . . . ?
C1 B1 C10 C15 -89.33(17) . . . . ?
C16 B1 C10 C11 -152.87(12) . . . . ?
C22 B1 C10 C11 -35.11(17) . . . . ?
C1 B1 C10 C11 84.24(16) . . . . ?
C15 C10 C11 C12 0.5(2) . . . . ?
B1 C10 C11 C12 -173.57(13) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C12 C13 C14 C15 -0.6(2) . . . . ?
C13 C14 C15 C10 0.5(2) . . . . ?
C11 C10 C15 C14 -0.4(2) . . . . ?
B1 C10 C15 C14 173.48(13) . . . . ?
C10 B1 C16 C17 33.04(19) . . . . ?
C22 B1 C16 C17 -87.29(16) . . . . ?
C1 B1 C16 C17 155.48(14) . . . . ?
C10 B1 C16 C21 -154.20(13) . . . . ?
C22 B1 C16 C21 85.46(15) . . . . ?
C1 B1 C16 C21 -31.76(18) . . . . ?
C21 C16 C17 C18 0.6(2) . . . . ?
B1 C16 C17 C18 173.86(14) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C21 0.3(2) . . . . ?
C19 C20 C21 C16 -0.4(2) . . . . ?
C17 C16 C21 C20 -0.1(2) . . . . ?
B1 C16 C21 C20 -173.38(14) . . . . ?
C10 B1 C22 C27 132.92(15) . . . . ?
C16 B1 C22 C27 -104.47(17) . . . . ?
C1 B1 C22 C27 13.4(2) . . . . ?
C10 B1 C22 C23 -49.64(17) . . . . ?
C16 B1 C22 C23 72.97(16) . . . . ?
C1 B1 C22 C23 -169.11(13) . . . . ?
C27 C22 C23 C24 -1.0(2) . . . . ?
B1 C22 C23 C24 -178.74(14) . . . . ?
C22 C23 C24 C25 0.3(2) . . . . ?
C23 C24 C25 C26 0.7(3) . . . . ?
C24 C25 C26 C27 -0.9(3) . . . . ?
C25 C26 C27 C22 0.1(3) . . . . ?
C23 C22 C27 C26 0.8(2) . . . . ?
B1 C22 C27 C26 178.34(16) . . . . ?

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_jcs077_compound_2b
_database_code_depnum_ccdc_archive 'CCDC 1555967'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ((di-tert-butylphosphonio)methyl)(3,3-dimethylbut-1-yn-1-yl)diphenylborate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H40 B P'
_chemical_formula_sum            'C27 H40 B P'
_chemical_formula_weight         406.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0726(4)
_cell_length_b                   11.0362(4)
_cell_length_c                   12.2129(4)
_cell_angle_alpha                88.259(1)
_cell_angle_beta                 69.614(1)
_cell_angle_gamma                78.174(1)
_cell_volume                     1244.34(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.5

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9362
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 3+1 runs, 654 frames, 40 sec./frame
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with Photon100 detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            21399
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.205
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5620
_reflns_number_gt                4651
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       APEX3
_computing_cell_refinement       APEX3
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    shelxtl
_computing_publication_material  publCIF

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+0.5744P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0122(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5620
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.62129(4) 0.70270(3) 0.21930(3) 0.01319(10) Uani 1 1 d . . . . .
H1 H 0.5268(16) 0.7895(13) 0.2931(12) 0.016 Uiso 1 1 d . U . . .
B1 B 0.35367(16) 0.60231(13) 0.27465(12) 0.0144(3) Uani 1 1 d . . . . .
C1 C 0.53450(14) 0.58250(12) 0.20245(11) 0.0153(3) Uani 1 1 d . . . . .
H1A H 0.5528 0.5705 0.1180 0.018 Uiso 1 1 calc R U . . .
H1B H 0.5821 0.5048 0.2278 0.018 Uiso 1 1 calc R U . . .
C2 C 0.75377(15) 0.64436(12) 0.29187(12) 0.0188(3) Uani 1 1 d . . . . .
C3 C 0.67332(16) 0.58075(13) 0.40183(12) 0.0228(3) Uani 1 1 d . . . . .
H3A H 0.5911 0.6411 0.4532 0.034 Uiso 1 1 calc R U . . .
H3B H 0.6381 0.5127 0.3789 0.034 Uiso 1 1 calc R U . . .
H3C H 0.7396 0.5480 0.4434 0.034 Uiso 1 1 calc R U . . .
C4 C 0.88252(16) 0.55068(15) 0.21107(14) 0.0300(4) Uani 1 1 d . . . . .
H4A H 0.8475 0.4832 0.1868 0.045 Uiso 1 1 calc R U . . .
H4B H 0.9342 0.5920 0.1419 0.045 Uiso 1 1 calc R U . . .
H4C H 0.9483 0.5168 0.2528 0.045 Uiso 1 1 calc R U . . .
C5 C 0.8058(2) 0.75108(16) 0.33120(16) 0.0363(4) Uani 1 1 d . . . . .
H5A H 0.7222 0.8101 0.3828 0.054 Uiso 1 1 calc R U . . .
H5B H 0.8712 0.7181 0.3734 0.054 Uiso 1 1 calc R U . . .
H5C H 0.8571 0.7932 0.2625 0.054 Uiso 1 1 calc R U . . .
C6 C 0.68350(15) 0.78660(13) 0.08364(12) 0.0189(3) Uani 1 1 d . . . . .
C7 C 0.55061(17) 0.82808(16) 0.04669(14) 0.0300(4) Uani 1 1 d . . . . .
H7A H 0.4727 0.8802 0.1097 0.045 Uiso 1 1 calc R U . . .
H7B H 0.5767 0.8754 -0.0241 0.045 Uiso 1 1 calc R U . . .
H7C H 0.5177 0.7550 0.0309 0.045 Uiso 1 1 calc R U . . .
C8 C 0.80541(17) 0.70510(16) -0.01463(13) 0.0312(4) Uani 1 1 d . . . . .
H8A H 0.7732 0.6313 -0.0295 0.047 Uiso 1 1 calc R U . . .
H8B H 0.8305 0.7519 -0.0858 0.047 Uiso 1 1 calc R U . . .
H8C H 0.8906 0.6799 0.0086 0.047 Uiso 1 1 calc R U . . .
C9 C 0.7319(2) 0.90280(15) 0.10833(15) 0.0333(4) Uani 1 1 d . . . . .
H9A H 0.6531 0.9542 0.1713 0.050 Uiso 1 1 calc R U . . .
H9B H 0.8169 0.8782 0.1319 0.050 Uiso 1 1 calc R U . . .
H9C H 0.7568 0.9502 0.0375 0.050 Uiso 1 1 calc R U . . .
C10 C 0.27027(13) 0.68316(12) 0.19386(11) 0.0146(3) Uani 1 1 d . . . . .
C11 C 0.19536(14) 0.80624(13) 0.21986(11) 0.0190(3) Uani 1 1 d . . . . .
H11 H 0.1850 0.8451 0.2916 0.023 Uiso 1 1 calc R U . . .
C12 C 0.13544(15) 0.87373(14) 0.14401(12) 0.0241(3) Uani 1 1 d . . . . .
H12 H 0.0868 0.9577 0.1639 0.029 Uiso 1 1 calc R U . . .
C13 C 0.14631(15) 0.81918(14) 0.03965(12) 0.0229(3) Uani 1 1 d . . . . .
H13 H 0.1057 0.8651 -0.0123 0.027 Uiso 1 1 calc R U . . .
C14 C 0.21728(15) 0.69667(14) 0.01229(12) 0.0221(3) Uani 1 1 d . . . . .
H14 H 0.2248 0.6577 -0.0585 0.026 Uiso 1 1 calc R U . . .
C15 C 0.27754(15) 0.63070(13) 0.08822(11) 0.0188(3) Uani 1 1 d . . . . .
H15 H 0.3256 0.5467 0.0678 0.023 Uiso 1 1 calc R U . . .
C16 C 0.31039(14) 0.46618(12) 0.29323(11) 0.0147(3) Uani 1 1 d . . . . .
C17 C 0.16726(15) 0.45760(13) 0.35837(12) 0.0194(3) Uani 1 1 d . . . . .
H17 H 0.0983 0.5317 0.3907 0.023 Uiso 1 1 calc R U . . .
C18 C 0.12215(16) 0.34568(14) 0.37758(12) 0.0239(3) Uani 1 1 d . . . . .
H18 H 0.0241 0.3443 0.4221 0.029 Uiso 1 1 calc R U . . .
C19 C 0.22009(17) 0.23603(14) 0.33186(13) 0.0249(3) Uani 1 1 d . . . . .
H19 H 0.1903 0.1589 0.3453 0.030 Uiso 1 1 calc R U . . .
C20 C 0.36175(17) 0.24045(13) 0.26648(13) 0.0250(3) Uani 1 1 d . . . . .
H20 H 0.4300 0.1659 0.2345 0.030 Uiso 1 1 calc R U . . .
C21 C 0.40502(15) 0.35386(12) 0.24727(12) 0.0202(3) Uani 1 1 d . . . . .
H21 H 0.5027 0.3546 0.2011 0.024 Uiso 1 1 calc R U . . .
C22 C 0.31144(14) 0.67661(12) 0.39628(11) 0.0145(3) Uani 1 1 d . . . . .
C23 C 0.28301(14) 0.74345(12) 0.48112(11) 0.0158(3) Uani 1 1 d . . . . .
C24 C 0.24788(15) 0.83424(12) 0.57926(11) 0.0172(3) Uani 1 1 d . . . . .
C25 C 0.12705(17) 0.94069(13) 0.57285(14) 0.0266(3) Uani 1 1 d . . . . .
H25A H 0.1026 1.0016 0.6373 0.040 Uiso 1 1 calc R U . . .
H25B H 0.1598 0.9805 0.4981 0.040 Uiso 1 1 calc R U . . .
H25C H 0.0413 0.9081 0.5790 0.040 Uiso 1 1 calc R U . . .
C26 C 0.1977(2) 0.77410(15) 0.69717(13) 0.0368(4) Uani 1 1 d . . . . .
H26A H 0.1752 0.8359 0.7605 0.055 Uiso 1 1 calc R U . . .
H26B H 0.1109 0.7422 0.7053 0.055 Uiso 1 1 calc R U . . .
H26C H 0.2748 0.7057 0.7013 0.055 Uiso 1 1 calc R U . . .
C27 C 0.38152(17) 0.88668(15) 0.56754(15) 0.0325(4) Uani 1 1 d . . . . .
H27A H 0.3580 0.9467 0.6325 0.049 Uiso 1 1 calc R U . . .
H27B H 0.4607 0.8190 0.5693 0.049 Uiso 1 1 calc R U . . .
H27C H 0.4113 0.9279 0.4933 0.049 Uiso 1 1 calc R U . . .


_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 1.7843(13) . ?
P1 C6 1.8484(13) . ?
P1 C2 1.8487(14) . ?
P1 H1 1.310(14) . ?
B1 C22 1.5971(18) . ?
B1 C16 1.6363(19) . ?
B1 C10 1.6408(19) . ?
B1 C1 1.6948(19) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C4 1.531(2) . ?
C2 C5 1.534(2) . ?
C2 C3 1.5397(19) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C8 1.531(2) . ?
C6 C9 1.535(2) . ?
C6 C7 1.537(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.3980(18) . ?
C10 C15 1.4026(18) . ?
C11 C12 1.3931(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3886(19) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.3948(18) . ?
C16 C17 1.4045(19) . ?
C17 C18 1.388(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.2053(18) . ?
C23 C24 1.4825(17) . ?
C24 C26 1.5304(19) . ?
C24 C25 1.5305(19) . ?
C24 C27 1.532(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C1 P1 C6 112.29(6) . . ?
C1 P1 C2 110.21(6) . . ?
C6 P1 C2 117.49(6) . . ?
C1 P1 H1 109.6(7) . . ?
C6 P1 H1 102.8(6) . . ?
C2 P1 H1 103.5(6) . . ?
C22 B1 C16 111.87(10) . . ?
C22 B1 C10 109.35(10) . . ?
C16 B1 C10 109.23(10) . . ?
C22 B1 C1 109.37(11) . . ?
C16 B1 C1 108.73(10) . . ?
C10 B1 C1 108.22(10) . . ?
B1 C1 P1 117.62(9) . . ?
B1 C1 H1A 107.9 . . ?
P1 C1 H1A 107.9 . . ?
B1 C1 H1B 107.9 . . ?
P1 C1 H1B 107.9 . . ?
H1A C1 H1B 107.2 . . ?
C4 C2 C5 110.52(13) . . ?
C4 C2 C3 109.86(12) . . ?
C5 C2 C3 108.00(12) . . ?
C4 C2 P1 110.70(10) . . ?
C5 C2 P1 111.21(10) . . ?
C3 C2 P1 106.42(9) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C6 C9 110.26(13) . . ?
C8 C6 C7 109.61(12) . . ?
C9 C6 C7 108.25(12) . . ?
C8 C6 P1 112.51(10) . . ?
C9 C6 P1 110.18(10) . . ?
C7 C6 P1 105.84(9) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 115.79(12) . . ?
C11 C10 B1 124.37(11) . . ?
C15 C10 B1 119.78(11) . . ?
C12 C11 C10 122.12(13) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C13 C12 C11 120.43(13) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 118.93(13) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 120.07(13) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 122.63(13) . . ?
C14 C15 H15 118.7 . . ?
C10 C15 H15 118.7 . . ?
C21 C16 C17 115.33(12) . . ?
C21 C16 B1 125.16(12) . . ?
C17 C16 B1 119.50(11) . . ?
C18 C17 C16 122.88(13) . . ?
C18 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
C19 C18 C17 119.97(13) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 118.99(13) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 120.30(14) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 122.52(13) . . ?
C16 C21 H21 118.7 . . ?
C20 C21 H21 118.7 . . ?
C23 C22 B1 173.02(13) . . ?
C22 C23 C24 175.38(13) . . ?
C23 C24 C26 111.06(11) . . ?
C23 C24 C25 108.52(11) . . ?
C26 C24 C25 109.37(12) . . ?
C23 C24 C27 109.63(11) . . ?
C26 C24 C27 109.56(13) . . ?
C25 C24 C27 108.65(12) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

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
C22 B1 C1 P1 -33.87(14) . . . . ?
C16 B1 C1 P1 -156.28(9) . . . . ?
C10 B1 C1 P1 85.17(12) . . . . ?
C6 P1 C1 B1 -110.74(10) . . . . ?
C2 P1 C1 B1 116.23(10) . . . . ?
C1 P1 C2 C4 68.96(11) . . . . ?
C6 P1 C2 C4 -61.36(12) . . . . ?
C1 P1 C2 C5 -167.76(11) . . . . ?
C6 P1 C2 C5 61.92(13) . . . . ?
C1 P1 C2 C3 -50.37(11) . . . . ?
C6 P1 C2 C3 179.30(9) . . . . ?
C1 P1 C6 C8 -66.74(12) . . . . ?
C2 P1 C6 C8 62.62(12) . . . . ?
C1 P1 C6 C9 169.78(10) . . . . ?
C2 P1 C6 C9 -60.86(12) . . . . ?
C1 P1 C6 C7 52.96(12) . . . . ?
C2 P1 C6 C7 -177.69(10) . . . . ?
C22 B1 C10 C11 10.29(17) . . . . ?
C16 B1 C10 C11 133.02(13) . . . . ?
C1 B1 C10 C11 -108.76(14) . . . . ?
C22 B1 C10 C15 -172.83(11) . . . . ?
C16 B1 C10 C15 -50.10(15) . . . . ?
C1 B1 C10 C15 68.12(15) . . . . ?
C15 C10 C11 C12 -1.9(2) . . . . ?
B1 C10 C11 C12 175.14(13) . . . . ?
C10 C11 C12 C13 1.2(2) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
C13 C14 C15 C10 -0.1(2) . . . . ?
C11 C10 C15 C14 1.3(2) . . . . ?
B1 C10 C15 C14 -175.80(12) . . . . ?
C22 B1 C16 C21 -126.41(13) . . . . ?
C10 B1 C16 C21 112.38(14) . . . . ?
C1 B1 C16 C21 -5.53(17) . . . . ?
C22 B1 C16 C17 54.72(15) . . . . ?
C10 B1 C16 C17 -66.49(14) . . . . ?
C1 B1 C16 C17 175.60(11) . . . . ?
C21 C16 C17 C18 0.79(19) . . . . ?
B1 C16 C17 C18 179.77(12) . . . . ?
C16 C17 C18 C19 0.1(2) . . . . ?
C17 C18 C19 C20 -0.6(2) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C17 C16 C21 C20 -1.3(2) . . . . ?
B1 C16 C21 C20 179.80(13) . . . . ?
C19 C20 C21 C16 0.9(2) . . . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_l0825b
_database_code_depnum_ccdc_archive 'CCDC 1557521'
_audit_update_record             
;
2017-06-21 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H39 B N P'
_chemical_formula_sum            'C26 H39 B N P'
_chemical_formula_weight         407.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   11.4364(4)
_cell_length_b                   14.5007(5)
_cell_length_c                   14.8879(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.698(2)
_cell_angle_gamma                90
_cell_volume                     2463.80(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    59068
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      35.05

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7101
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_process_details   SADABS-2014/4
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            71268
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.271
_diffrn_reflns_theta_max         35.008
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10849
_reflns_number_gt                9694
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       Apex2
_computing_cell_refinement       Peakref
_computing_data_reduction        'Eval15, SADABS-2014/4'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0743P)²+0.5075P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 4312 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         10849
_refine_ls_number_parameters     279
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1258
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.38441(3) 0.28130(3) 0.12277(3) 0.03117(9) Uani 1 1 d . . . . .
N1 N 0.40308(14) 0.38001(11) -0.02357(12) 0.0397(3) Uani 1 1 d . . . . .
C1 C 0.48947(16) 0.23320(13) 0.05286(11) 0.0361(3) Uani 1 1 d . . . . .
H1A H 0.470(3) 0.177(3) 0.036(2) 0.065(10) Uiso 1 1 d . . . . .
H1B H 0.563(3) 0.231(2) 0.086(2) 0.051(8) Uiso 1 1 d . . . . .
C2 C 0.4640(2) 0.3218(2) 0.22788(16) 0.0598(7) Uani 1 1 d . . . . .
C3 C 0.5222(3) 0.2380(3) 0.27716(17) 0.0777(10) Uani 1 1 d . . . . .
H3A H 0.5755 0.2598 0.3269 0.117 Uiso 1 1 calc R U . . .
H3B H 0.5665 0.2024 0.2349 0.117 Uiso 1 1 calc R U . . .
H3C H 0.4616 0.1989 0.3009 0.117 Uiso 1 1 calc R U . . .
C4 C 0.3853(4) 0.3757(4) 0.2901(3) 0.1049(18) Uani 1 1 d . . . . .
H4A H 0.3211 0.3359 0.3072 0.157 Uiso 1 1 calc R U . . .
H4B H 0.3530 0.4301 0.2584 0.157 Uiso 1 1 calc R U . . .
H4C H 0.4319 0.3952 0.3444 0.157 Uiso 1 1 calc R U . . .
C5 C 0.5589(3) 0.3892(3) 0.1970(2) 0.0763(9) Uani 1 1 d . . . . .
H5A H 0.6048 0.4131 0.2499 0.114 Uiso 1 1 calc R U . . .
H5B H 0.5211 0.4405 0.1638 0.114 Uiso 1 1 calc R U . . .
H5C H 0.6109 0.3565 0.1580 0.114 Uiso 1 1 calc R U . . .
C6 C 0.26623(15) 0.19415(11) 0.13568(12) 0.0346(3) Uani 1 1 d . . . . .
C7 C 0.1952(2) 0.19082(18) 0.04441(18) 0.0548(5) Uani 1 1 d . . . . .
H7A H 0.2487 0.1833 -0.0039 0.082 Uiso 1 1 calc R U . . .
H7B H 0.1511 0.2484 0.0353 0.082 Uiso 1 1 calc R U . . .
H7C H 0.1406 0.1387 0.0437 0.082 Uiso 1 1 calc R U . . .
C8 C 0.3182(2) 0.09791(13) 0.15386(17) 0.0482(4) Uani 1 1 d . . . . .
H8A H 0.3713 0.0997 0.2082 0.072 Uiso 1 1 calc R U . . .
H8B H 0.3617 0.0785 0.1025 0.072 Uiso 1 1 calc R U . . .
H8C H 0.2548 0.0540 0.1625 0.072 Uiso 1 1 calc R U . . .
C9 C 0.1857(2) 0.21511(16) 0.21198(18) 0.0506(5) Uani 1 1 d . . . . .
H9A H 0.1230 0.1691 0.2115 0.076 Uiso 1 1 calc R U . . .
H9B H 0.1515 0.2766 0.2031 0.076 Uiso 1 1 calc R U . . .
H9C H 0.2315 0.2130 0.2699 0.076 Uiso 1 1 calc R U . . .
C10 C 0.45351(15) 0.24821(13) -0.12871(11) 0.0369(3) Uani 1 1 d . . . . .
C11 C 0.4911(2) 0.15903(16) -0.14430(14) 0.0479(4) Uani 1 1 d . . . . .
H11 H 0.5407 0.1298 -0.0992 0.058 Uiso 1 1 calc R U . . .
C12 C 0.4596(3) 0.10967(19) -0.22338(16) 0.0567(6) Uani 1 1 d . . . . .
H12 H 0.4869 0.0484 -0.2304 0.068 Uiso 1 1 calc R U . . .
C13 C 0.3903(3) 0.1496(2) -0.28952(17) 0.0641(7) Uani 1 1 d . . . . .
H13 H 0.3685 0.1168 -0.3432 0.077 Uiso 1 1 calc R U . . .
C14 C 0.3520(3) 0.2383(3) -0.2778(2) 0.0721(9) Uani 1 1 d . . . . .
H14 H 0.3037 0.2669 -0.3241 0.087 Uiso 1 1 calc R U . . .
C15 C 0.3830(2) 0.28731(19) -0.19883(16) 0.0528(5) Uani 1 1 d . . . . .
H15 H 0.3554 0.3486 -0.1927 0.063 Uiso 1 1 calc R U . . .
C16 C 0.62200(14) 0.34960(11) -0.04585(9) 0.0313(3) Uani 1 1 d . . . . .
C17 C 0.72623(16) 0.30206(17) -0.02399(12) 0.0420(4) Uani 1 1 d . . . . .
H17 H 0.7221 0.2412 -0.0008 0.050 Uiso 1 1 calc R U . . .
C18 C 0.83630(17) 0.3406(2) -0.03496(13) 0.0499(5) Uani 1 1 d . . . . .
H18 H 0.9052 0.3064 -0.0185 0.060 Uiso 1 1 calc R U . . .
C19 C 0.84510(18) 0.42817(19) -0.06965(14) 0.0502(5) Uani 1 1 d . . . . .
H19 H 0.9198 0.4547 -0.0771 0.060 Uiso 1 1 calc R U . . .
C20 C 0.7439(2) 0.47712(16) -0.09364(15) 0.0481(4) Uani 1 1 d . . . . .
H20 H 0.7489 0.5372 -0.1186 0.058 Uiso 1 1 calc R U . . .
C21 C 0.63433(17) 0.43828(13) -0.08114(13) 0.0402(3) Uani 1 1 d . . . . .
H21 H 0.5659 0.4732 -0.0971 0.048 Uiso 1 1 calc R U . . .
C22 C 0.34150(17) 0.38079(12) 0.04223(17) 0.0458(4) Uani 1 1 d D . . . .
C23 C 0.2495(3) 0.45700(17) 0.0510(3) 0.0855(12) Uani 1 1 d D . . . .
C24 C 0.1552(4) 0.4368(2) 0.1146(4) 0.1128(19) Uani 1 1 d D . . . .
H24A H 0.1875 0.4435 0.1769 0.169 Uiso 1 1 calc R U . . .
H24B H 0.1267 0.3736 0.1050 0.169 Uiso 1 1 calc R U . . .
H24C H 0.0902 0.4801 0.1034 0.169 Uiso 1 1 calc R U . . .
C25 C 0.1863(4) 0.4683(3) -0.0439(4) 0.124(2) Uani 1 1 d D . . . .
H25A H 0.1530 0.4089 -0.0639 0.186 Uiso 1 1 calc R U . . .
H25B H 0.2427 0.4891 -0.0864 0.186 Uiso 1 1 calc R U . . .
H25C H 0.1234 0.5139 -0.0412 0.186 Uiso 1 1 calc R U . . .
C26 C 0.3141(5) 0.54622(19) 0.0712(4) 0.117(2) Uani 1 1 d D . . . .
H26A H 0.2586 0.5978 0.0670 0.175 Uiso 1 1 calc R U . . .
H26B H 0.3738 0.5551 0.0276 0.175 Uiso 1 1 calc R U . . .
H26C H 0.3520 0.5437 0.1321 0.175 Uiso 1 1 calc R U . . .
B1 B 0.49349(15) 0.30331(13) -0.03670(11) 0.0310(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.7818(16) . ?
P1 C2 1.854(2) . ?
P1 C6 1.8693(17) . ?
P1 C22 1.9194(18) . ?
N1 C22 1.243(3) . ?
N1 B1 1.540(2) . ?
C1 B1 1.680(2) . ?
C1 H1A 0.88(4) . ?
C1 H1B 0.95(3) . ?
C2 C4 1.545(4) . ?
C2 C3 1.547(5) . ?
C2 C5 1.552(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C8 1.534(2) . ?
C6 C9 1.538(3) . ?
C6 C7 1.538(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.387(3) . ?
C10 C15 1.398(3) . ?
C10 B1 1.626(3) . ?
C11 C12 1.405(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.354(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.374(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.400(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.397(2) . ?
C16 C21 1.400(2) . ?
C16 B1 1.629(2) . ?
C17 C18 1.397(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.397(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.538(3) . ?
C23 C24 1.509(4) . ?
C23 C26 1.511(5) . ?
C23 C25 1.553(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
C1 P1 C2 107.69(11) . . ?
C1 P1 C6 108.34(9) . . ?
C2 P1 C6 116.50(10) . . ?
C1 P1 C22 94.83(8) . . ?
C2 P1 C22 112.40(13) . . ?
C6 P1 C22 114.52(8) . . ?
C22 N1 B1 121.74(14) . . ?
B1 C1 P1 106.30(10) . . ?
B1 C1 H1A 111(2) . . ?
P1 C1 H1A 111(2) . . ?
B1 C1 H1B 111(2) . . ?
P1 C1 H1B 108(2) . . ?
H1A C1 H1B 109(3) . . ?
C4 C2 C3 111.2(3) . . ?
C4 C2 C5 107.7(3) . . ?
C3 C2 C5 110.3(3) . . ?
C4 C2 P1 113.1(3) . . ?
C3 C2 P1 108.9(2) . . ?
C5 C2 P1 105.34(18) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C6 C9 107.03(15) . . ?
C8 C6 C7 107.68(18) . . ?
C9 C6 C7 110.59(18) . . ?
C8 C6 P1 111.04(13) . . ?
C9 C6 P1 114.43(14) . . ?
C7 C6 P1 105.93(13) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 115.1(2) . . ?
C11 C10 B1 121.72(15) . . ?
C15 C10 B1 123.19(19) . . ?
C10 C11 C12 123.4(2) . . ?
C10 C11 H11 118.3 . . ?
C12 C11 H11 118.3 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 119.0(2) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 C15 121.1(3) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C10 C15 C14 121.6(3) . . ?
C10 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C17 C16 C21 115.82(16) . . ?
C17 C16 B1 122.54(15) . . ?
C21 C16 B1 121.54(15) . . ?
C18 C17 C16 122.5(2) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 119.29(18) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 122.24(19) . . ?
C20 C21 H21 118.9 . . ?
C16 C21 H21 118.9 . . ?
N1 C22 C23 119.95(19) . . ?
N1 C22 P1 110.51(13) . . ?
C23 C22 P1 129.50(18) . . ?
C24 C23 C26 113.7(4) . . ?
C24 C23 C22 115.7(2) . . ?
C26 C23 C22 107.7(3) . . ?
C24 C23 C25 106.4(4) . . ?
C26 C23 C25 106.5(4) . . ?
C22 C23 C25 106.2(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N1 B1 C10 107.90(14) . . ?
N1 B1 C16 109.25(14) . . ?
C10 B1 C16 109.77(13) . . ?
N1 B1 C1 106.46(13) . . ?
C10 B1 C1 110.54(14) . . ?
C16 B1 C1 112.75(13) . . ?

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
C2 P1 C1 B1 -112.90(15) . . . . ?
C6 P1 C1 B1 120.29(13) . . . . ?
C22 P1 C1 B1 2.46(14) . . . . ?
C1 P1 C2 C4 173.2(3) . . . . ?
C6 P1 C2 C4 -65.0(3) . . . . ?
C22 P1 C2 C4 70.0(3) . . . . ?
C1 P1 C2 C3 -62.60(19) . . . . ?
C6 P1 C2 C3 59.3(2) . . . . ?
C22 P1 C2 C3 -165.73(17) . . . . ?
C1 P1 C2 C5 55.7(3) . . . . ?
C6 P1 C2 C5 177.6(2) . . . . ?
C22 P1 C2 C5 -47.4(3) . . . . ?
C1 P1 C6 C8 44.29(16) . . . . ?
C2 P1 C6 C8 -77.24(18) . . . . ?
C22 P1 C6 C8 148.70(15) . . . . ?
C1 P1 C6 C9 165.58(14) . . . . ?
C2 P1 C6 C9 44.1(2) . . . . ?
C22 P1 C6 C9 -90.01(17) . . . . ?
C1 P1 C6 C7 -72.33(15) . . . . ?
C2 P1 C6 C7 166.14(18) . . . . ?
C22 P1 C6 C7 32.07(17) . . . . ?
C15 C10 C11 C12 -1.3(3) . . . . ?
B1 C10 C11 C12 -179.19(19) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C11 C10 C15 C14 1.0(3) . . . . ?
B1 C10 C15 C14 178.8(2) . . . . ?
C13 C14 C15 C10 -0.2(4) . . . . ?
C21 C16 C17 C18 1.1(3) . . . . ?
B1 C16 C17 C18 177.61(17) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C19 C20 C21 1.1(3) . . . . ?
C19 C20 C21 C16 -1.0(3) . . . . ?
C17 C16 C21 C20 -0.1(3) . . . . ?
B1 C16 C21 C20 -176.70(17) . . . . ?
B1 N1 C22 C23 -178.0(2) . . . . ?
B1 N1 C22 P1 3.8(3) . . . . ?
N1 C22 C23 C24 161.5(4) . . . . ?
P1 C22 C23 C24 -20.7(5) . . . . ?
N1 C22 C23 C26 -70.1(4) . . . . ?
P1 C22 C23 C26 107.7(3) . . . . ?
N1 C22 C23 C25 43.7(3) . . . . ?
P1 C22 C23 C25 -138.5(3) . . . . ?
C22 N1 B1 C10 116.7(2) . . . . ?
C22 N1 B1 C16 -124.0(2) . . . . ?
C22 N1 B1 C1 -1.9(3) . . . . ?
C11 C10 B1 N1 -158.12(17) . . . . ?
C15 C10 B1 N1 24.2(2) . . . . ?
C11 C10 B1 C16 82.92(19) . . . . ?
C15 C10 B1 C16 -94.8(2) . . . . ?
C11 C10 B1 C1 -42.1(2) . . . . ?
C15 C10 B1 C1 140.23(18) . . . . ?
C17 C16 B1 N1 154.67(15) . . . . ?
C21 C16 B1 N1 -29.0(2) . . . . ?
C17 C16 B1 C10 -87.20(17) . . . . ?
C21 C16 B1 C10 89.14(19) . . . . ?
C17 C16 B1 C1 36.5(2) . . . . ?
C21 C16 B1 C1 -147.15(16) . . . . ?
P1 C1 B1 N1 -1.10(18) . . . . ?
P1 C1 B1 C10 -118.04(14) . . . . ?
P1 C1 B1 C16 118.68(14) . . . . ?

_refine_diff_density_max         0.480
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.041

