# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1549900'
_audit_update_record             
;
2017-05-13 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H36 B N2 O2 P'
_chemical_formula_sum            'C33 H36 B N2 O2 P'
_chemical_formula_weight         534.42

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'
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                   9.6725(4)
_cell_length_b                   11.3305(4)
_cell_length_c                   14.4827(6)
_cell_angle_alpha                101.512(2)
_cell_angle_beta                 100.403(2)
_cell_angle_gamma                101.893(2)
_cell_volume                     1480.66(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6592
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      25.77

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'SADABS; Bruker,2014'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25932
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.902
_diffrn_reflns_theta_max         25.847
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5701
_reflns_number_gt                4172
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0339P)²+0.6260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5701
_refine_ls_number_parameters     358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C1 C 0.41456(18) 0.58017(16) 0.29752(12) 0.0182(4) Uani 1 1 d . . . . .
N1 N 0.53993(15) 0.68151(13) 0.32035(10) 0.0184(3) Uani 1 1 d . . . . .
N2 N 0.28470(15) 0.58921(14) 0.29200(11) 0.0215(3) Uani 1 1 d . . . . .
P1 P 0.44714(5) 0.42197(4) 0.27983(4) 0.01974(12) Uani 1 1 d . . . . .
C20 C 0.66258(18) 0.67358(16) 0.38854(12) 0.0179(4) Uani 1 1 d . . . . .
C21 C 0.80065(19) 0.69796(17) 0.37049(14) 0.0221(4) Uani 1 1 d . . . . .
H21 H 0.814776 0.722016 0.313005 0.027 Uiso 1 1 calc R U . . .
C22 C 0.9173(2) 0.68723(17) 0.43606(14) 0.0253(4) Uani 1 1 d . . . . .
H22 H 1.011455 0.705566 0.423583 0.030 Uiso 1 1 calc R U . . .
C23 C 0.8997(2) 0.65025(17) 0.51979(14) 0.0249(4) Uani 1 1 d . . . . .
C24 C 0.7615(2) 0.62409(17) 0.53601(14) 0.0256(4) Uani 1 1 d . . . . .
H24 H 0.746784 0.596829 0.592231 0.031 Uiso 1 1 calc R U . . .
C25 C 0.6441(2) 0.63687(17) 0.47193(13) 0.0225(4) Uani 1 1 d . . . . .
H25 H 0.550309 0.620352 0.485261 0.027 Uiso 1 1 calc R U . . .
C26 C 1.0279(2) 0.6406(2) 0.59197(16) 0.0393(6) Uani 1 1 d . . . . .
H26A H 1.055951 0.713444 0.647212 0.059 Uiso 1 1 calc R U . . .
H26B H 1.109642 0.637267 0.561040 0.059 Uiso 1 1 calc R U . . .
H26C H 1.001449 0.564894 0.614552 0.059 Uiso 1 1 calc R U . . .
C27 C 0.24928(19) 0.70497(17) 0.31745(14) 0.0216(4) Uani 1 1 d . . . . .
C28 C 0.3115(2) 0.79146(18) 0.40563(14) 0.0276(5) Uani 1 1 d . . . . .
H28 H 0.387843 0.777603 0.450199 0.033 Uiso 1 1 calc R U . . .
C29 C 0.2625(2) 0.89788(18) 0.42871(15) 0.0304(5) Uani 1 1 d . . . . .
H29 H 0.305624 0.955743 0.489462 0.037 Uiso 1 1 calc R U . . .
C30 C 0.1522(2) 0.92197(18) 0.36543(15) 0.0280(5) Uani 1 1 d . . . . .
C31 C 0.0922(2) 0.83566(18) 0.27740(15) 0.0290(5) Uani 1 1 d . . . . .
H31 H 0.017765 0.850730 0.232136 0.035 Uiso 1 1 calc R U . . .
C32 C 0.1382(2) 0.72817(18) 0.25389(14) 0.0256(4) Uani 1 1 d . . . . .
H32 H 0.093460 0.669630 0.193668 0.031 Uiso 1 1 calc R U . . .
C33 C 0.0946(3) 1.0346(2) 0.39298(17) 0.0421(6) Uani 1 1 d . . . . .
H33A H 0.093776 1.079480 0.341718 0.063 Uiso 1 1 calc R U . . .
H33B H 0.156914 1.089389 0.453791 0.063 Uiso 1 1 calc R U . . .
H33C H -0.004475 1.008169 0.401373 0.063 Uiso 1 1 calc R U . . .
C8 C 0.27979(19) 0.32907(17) 0.19205(13) 0.0210(4) Uani 1 1 d . . . . .
C9 C 0.2265(2) 0.21022(18) 0.20284(15) 0.0293(5) Uani 1 1 d . . . . .
H9 H 0.274220 0.183738 0.255334 0.035 Uiso 1 1 calc R U . . .
C10 C 0.1047(2) 0.1300(2) 0.13804(17) 0.0392(6) Uani 1 1 d . . . . .
H10 H 0.069620 0.049001 0.146338 0.047 Uiso 1 1 calc R U . . .
C11 C 0.0343(2) 0.1666(2) 0.06196(17) 0.0390(6) Uani 1 1 d . . . . .
H11 H -0.049065 0.111182 0.017408 0.047 Uiso 1 1 calc R U . . .
C12 C 0.0856(2) 0.2852(2) 0.05051(15) 0.0331(5) Uani 1 1 d . . . . .
H12 H 0.037421 0.310899 -0.002236 0.040 Uiso 1 1 calc R U . . .
C13 C 0.2064(2) 0.36594(18) 0.11533(14) 0.0264(4) Uani 1 1 d . . . . .
H13 H 0.239753 0.447471 0.107494 0.032 Uiso 1 1 calc R U . . .
C2 C 0.58021(19) 0.43513(16) 0.20468(13) 0.0200(4) Uani 1 1 d . . . . .
C7 C 0.6905(2) 0.37479(18) 0.22038(14) 0.0260(4) Uani 1 1 d . . . . .
H7 H 0.692498 0.327293 0.267530 0.031 Uiso 1 1 calc R U . . .
C6 C 0.7972(2) 0.3829(2) 0.16839(15) 0.0336(5) Uani 1 1 d . . . . .
H6 H 0.870942 0.339923 0.179027 0.040 Uiso 1 1 calc R U . . .
C5 C 0.7964(2) 0.4533(2) 0.10114(15) 0.0323(5) Uani 1 1 d . . . . .
H5 H 0.870159 0.459620 0.065738 0.039 Uiso 1 1 calc R U . . .
C4 C 0.6886(2) 0.51480(19) 0.08516(14) 0.0296(5) Uani 1 1 d . . . . .
H4 H 0.688738 0.564054 0.039216 0.036 Uiso 1 1 calc R U . . .
C3 C 0.5804(2) 0.50491(17) 0.13579(13) 0.0233(4) Uani 1 1 d . . . . .
H3 H 0.505383 0.546134 0.123457 0.028 Uiso 1 1 calc R U . . .
B1 B 0.5453(2) 0.77446(19) 0.26634(16) 0.0208(5) Uani 1 1 d . . . . .
O1 O 0.65425(14) 0.88095(12) 0.28935(10) 0.0292(3) Uani 1 1 d . . . . .
O2 O 0.44180(13) 0.76156(11) 0.18448(9) 0.0243(3) Uani 1 1 d . . . . .
C14 C 0.6057(2) 0.95861(18) 0.22687(15) 0.0290(5) Uani 1 1 d . . . . .
C15 C 0.4960(2) 0.86112(18) 0.13992(15) 0.0279(5) Uani 1 1 d . . . . .
C16 C 0.7375(2) 1.0314(2) 0.20157(18) 0.0434(6) Uani 1 1 d . . . . .
H16A H 0.801828 1.089175 0.260452 0.065 Uiso 1 1 calc R U . . .
H16B H 0.706342 1.078344 0.155220 0.065 Uiso 1 1 calc R U . . .
H16C H 0.789739 0.973687 0.172682 0.065 Uiso 1 1 calc R U . . .
C17 C 0.5362(3) 1.0461(2) 0.28548(17) 0.0412(6) Uani 1 1 d . . . . .
H17A H 0.451901 0.997659 0.301911 0.062 Uiso 1 1 calc R U . . .
H17B H 0.504829 1.102207 0.247301 0.062 Uiso 1 1 calc R U . . .
H17C H 0.606892 1.095091 0.345111 0.062 Uiso 1 1 calc R U . . .
C18 C 0.5668(3) 0.8055(2) 0.06228(16) 0.0417(6) Uani 1 1 d . . . . .
H18A H 0.650932 0.779758 0.092561 0.063 Uiso 1 1 calc R U . . .
H18B H 0.598436 0.867813 0.027215 0.063 Uiso 1 1 calc R U . . .
H18C H 0.496585 0.733029 0.016931 0.063 Uiso 1 1 calc R U . . .
C19 C 0.3672(2) 0.9041(2) 0.09515(17) 0.0440(6) Uani 1 1 d . . . . .
H19A H 0.304191 0.837178 0.041049 0.066 Uiso 1 1 calc R U . . .
H19B H 0.401643 0.977426 0.071425 0.066 Uiso 1 1 calc R U . . .
H19C H 0.312419 0.925541 0.144020 0.066 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
C1 N2 1.271(2) . ?
C1 N1 1.424(2) . ?
C1 P1 1.8592(18) . ?
N1 B1 1.430(2) . ?
N1 C20 1.431(2) . ?
N2 C27 1.418(2) . ?
P1 C2 1.8317(18) . ?
P1 C8 1.8343(19) . ?
C20 C25 1.383(2) . ?
C20 C21 1.390(2) . ?
C21 C22 1.380(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(3) . ?
C23 C26 1.509(3) . ?
C24 C25 1.383(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C32 1.388(3) . ?
C27 C28 1.391(3) . ?
C28 C29 1.387(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.385(3) . ?
C30 C33 1.506(3) . ?
C31 C32 1.382(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C8 C9 1.390(3) . ?
C8 C13 1.391(3) . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.370(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C2 C7 1.390(3) . ?
C2 C3 1.391(2) . ?
C7 C6 1.382(3) . ?
C7 H7 0.9500 . ?
C6 C5 1.377(3) . ?
C6 H6 0.9500 . ?
C5 C4 1.380(3) . ?
C5 H5 0.9500 . ?
C4 C3 1.381(3) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
B1 O1 1.366(2) . ?
B1 O2 1.368(2) . ?
O1 C14 1.466(2) . ?
O2 C15 1.460(2) . ?
C14 C16 1.516(3) . ?
C14 C17 1.517(3) . ?
C14 C15 1.553(3) . ?
C15 C19 1.515(3) . ?
C15 C18 1.517(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
N2 C1 N1 125.72(16) . . ?
N2 C1 P1 117.93(13) . . ?
N1 C1 P1 116.30(12) . . ?
C1 N1 B1 119.92(15) . . ?
C1 N1 C20 116.10(14) . . ?
B1 N1 C20 123.38(14) . . ?
C1 N2 C27 122.71(15) . . ?
C2 P1 C8 102.74(8) . . ?
C2 P1 C1 100.54(8) . . ?
C8 P1 C1 101.19(8) . . ?
C25 C20 C21 119.05(16) . . ?
C25 C20 N1 120.13(15) . . ?
C21 C20 N1 120.78(15) . . ?
C22 C21 C20 120.02(17) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 121.34(17) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 118.07(17) . . ?
C24 C23 C26 120.81(18) . . ?
C22 C23 C26 121.11(18) . . ?
C23 C24 C25 121.21(17) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C20 C25 C24 120.28(17) . . ?
C20 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
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 118.46(17) . . ?
C32 C27 N2 117.82(17) . . ?
C28 C27 N2 123.52(17) . . ?
C29 C28 C27 120.19(18) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C30 C29 C28 121.68(19) . . ?
C30 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?
C31 C30 C29 117.51(18) . . ?
C31 C30 C33 121.09(19) . . ?
C29 C30 C33 121.34(19) . . ?
C32 C31 C30 121.55(18) . . ?
C32 C31 H31 119.2 . . ?
C30 C31 H31 119.2 . . ?
C31 C32 C27 120.60(18) . . ?
C31 C32 H32 119.7 . . ?
C27 C32 H32 119.7 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C9 C8 C13 118.35(17) . . ?
C9 C8 P1 115.84(14) . . ?
C13 C8 P1 125.78(14) . . ?
C10 C9 C8 120.76(19) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.49(19) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C8 120.59(19) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C7 C2 C3 118.38(17) . . ?
C7 C2 P1 117.44(14) . . ?
C3 C2 P1 124.13(14) . . ?
C6 C7 C2 120.96(18) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
C5 C6 C7 119.84(19) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C5 C4 120.03(18) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 C3 120.17(19) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C3 C2 120.61(17) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O1 B1 O2 114.16(16) . . ?
O1 B1 N1 123.81(17) . . ?
O2 B1 N1 122.01(17) . . ?
B1 O1 C14 105.95(14) . . ?
B1 O2 C15 106.51(14) . . ?
O1 C14 C16 108.28(16) . . ?
O1 C14 C17 106.47(16) . . ?
C16 C14 C17 110.48(18) . . ?
O1 C14 C15 102.51(14) . . ?
C16 C14 C15 114.77(18) . . ?
C17 C14 C15 113.56(17) . . ?
O2 C15 C19 107.81(16) . . ?
O2 C15 C18 106.80(15) . . ?
C19 C15 C18 110.53(18) . . ?
O2 C15 C14 102.40(14) . . ?
C19 C15 C14 115.03(17) . . ?
C18 C15 C14 113.46(17) . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
N2 C1 N1 B1 -53.4(3) . . . . ?
P1 C1 N1 B1 129.42(15) . . . . ?
N2 C1 N1 C20 135.18(18) . . . . ?
P1 C1 N1 C20 -41.98(19) . . . . ?
N1 C1 N2 C27 -6.2(3) . . . . ?
P1 C1 N2 C27 170.93(13) . . . . ?
N2 C1 P1 C2 138.21(14) . . . . ?
N1 C1 P1 C2 -44.40(14) . . . . ?
N2 C1 P1 C8 32.81(16) . . . . ?
N1 C1 P1 C8 -149.80(13) . . . . ?
C1 N1 C20 C25 -44.7(2) . . . . ?
B1 N1 C20 C25 144.21(18) . . . . ?
C1 N1 C20 C21 132.88(17) . . . . ?
B1 N1 C20 C21 -38.2(3) . . . . ?
C25 C20 C21 C22 -1.0(3) . . . . ?
N1 C20 C21 C22 -178.59(16) . . . . ?
C20 C21 C22 C23 1.1(3) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C21 C22 C23 C26 -179.03(18) . . . . ?
C22 C23 C24 C25 -1.4(3) . . . . ?
C26 C23 C24 C25 177.71(18) . . . . ?
C21 C20 C25 C24 -0.3(3) . . . . ?
N1 C20 C25 C24 177.30(16) . . . . ?
C23 C24 C25 C20 1.5(3) . . . . ?
C1 N2 C27 C32 132.96(18) . . . . ?
C1 N2 C27 C28 -52.4(3) . . . . ?
C32 C27 C28 C29 0.2(3) . . . . ?
N2 C27 C28 C29 -174.45(17) . . . . ?
C27 C28 C29 C30 -0.5(3) . . . . ?
C28 C29 C30 C31 -0.2(3) . . . . ?
C28 C29 C30 C33 176.99(19) . . . . ?
C29 C30 C31 C32 1.3(3) . . . . ?
C33 C30 C31 C32 -175.96(18) . . . . ?
C30 C31 C32 C27 -1.6(3) . . . . ?
C28 C27 C32 C31 0.9(3) . . . . ?
N2 C27 C32 C31 175.78(17) . . . . ?
C2 P1 C8 C9 112.41(15) . . . . ?
C1 P1 C8 C9 -143.95(15) . . . . ?
C2 P1 C8 C13 -65.37(17) . . . . ?
C1 P1 C8 C13 38.27(18) . . . . ?
C13 C8 C9 C10 0.9(3) . . . . ?
P1 C8 C9 C10 -177.03(16) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C8 1.1(3) . . . . ?
C9 C8 C13 C12 -1.4(3) . . . . ?
P1 C8 C13 C12 176.31(15) . . . . ?
C8 P1 C2 C7 -112.59(15) . . . . ?
C1 P1 C2 C7 143.27(15) . . . . ?
C8 P1 C2 C3 69.74(17) . . . . ?
C1 P1 C2 C3 -34.40(17) . . . . ?
C3 C2 C7 C6 -0.5(3) . . . . ?
P1 C2 C7 C6 -178.32(15) . . . . ?
C2 C7 C6 C5 1.1(3) . . . . ?
C7 C6 C5 C4 -0.6(3) . . . . ?
C6 C5 C4 C3 -0.6(3) . . . . ?
C5 C4 C3 C2 1.3(3) . . . . ?
C7 C2 C3 C4 -0.7(3) . . . . ?
P1 C2 C3 C4 176.96(15) . . . . ?
C1 N1 B1 O1 173.12(17) . . . . ?
C20 N1 B1 O1 -16.1(3) . . . . ?
C1 N1 B1 O2 -8.8(3) . . . . ?
C20 N1 B1 O2 161.92(16) . . . . ?
O2 B1 O1 C14 11.2(2) . . . . ?
N1 B1 O1 C14 -170.58(18) . . . . ?
O1 B1 O2 C15 8.3(2) . . . . ?
N1 B1 O2 C15 -169.89(17) . . . . ?
B1 O1 C14 C16 -146.09(18) . . . . ?
B1 O1 C14 C17 95.10(18) . . . . ?
B1 O1 C14 C15 -24.41(19) . . . . ?
B1 O2 C15 C19 -144.51(17) . . . . ?
B1 O2 C15 C18 96.68(18) . . . . ?
B1 O2 C15 C14 -22.80(18) . . . . ?
O1 C14 C15 O2 28.60(18) . . . . ?
C16 C14 C15 O2 145.75(16) . . . . ?
C17 C14 C15 O2 -85.82(18) . . . . ?
O1 C14 C15 C19 145.25(17) . . . . ?
C16 C14 C15 C19 -97.6(2) . . . . ?
C17 C14 C15 C19 30.8(2) . . . . ?
O1 C14 C15 C18 -86.11(18) . . . . ?
C16 C14 C15 C18 31.0(2) . . . . ?
C17 C14 C15 C18 159.47(17) . . . . ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1549899'
_audit_update_record             
;
2017-05-13 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H36 B N2 O2 P'
_chemical_formula_sum            'C25 H36 B N2 O2 P'
_chemical_formula_weight         438.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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                   10.7605(4)
_cell_length_b                   11.2811(4)
_cell_length_c                   12.5055(4)
_cell_angle_alpha                111.6550(10)
_cell_angle_beta                 98.380(2)
_cell_angle_gamma                110.8890(10)
_cell_volume                     1249.14(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7596
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      26.75

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.474
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'SADABS; Bruker, 2014'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29421
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_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         3.114
_diffrn_reflns_theta_max         26.862
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5350
_reflns_number_gt                4055
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0421P)²+0.3982P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5350
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.50507(16) 0.23994(16) 0.66819(14) 0.0164(3) Uani 1 1 d . . . . .
N1 N 0.38694(13) 0.24675(14) 0.60634(11) 0.0171(3) Uani 1 1 d . . . . .
N2 N 0.62985(14) 0.33656(15) 0.71446(13) 0.0229(3) Uani 1 1 d . . . . .
P1 P 0.46763(4) 0.06312(4) 0.66347(4) 0.01887(11) Uani 1 1 d . . . . .
C20 C 0.31469(18) 0.14188(18) 0.47535(14) 0.0220(4) Uani 1 1 d . . . . .
H20 H 0.358533 0.075191 0.455148 0.026 Uiso 1 1 calc R U . . .
C21 C 0.3381(2) 0.2162(2) 0.39533(16) 0.0323(4) Uani 1 1 d . . . . .
H21A H 0.295057 0.281619 0.412101 0.048 Uiso 1 1 calc R U . . .
H21B H 0.295275 0.144978 0.309785 0.048 Uiso 1 1 calc R U . . .
H21C H 0.439068 0.270036 0.412507 0.048 Uiso 1 1 calc R U . . .
C22 C 0.16001(19) 0.05337(19) 0.45068(17) 0.0314(4) Uani 1 1 d . . . . .
H22A H 0.149583 0.004241 0.501515 0.047 Uiso 1 1 calc R U . . .
H22B H 0.116728 -0.017100 0.364909 0.047 Uiso 1 1 calc R U . . .
H22C H 0.113773 0.115775 0.469670 0.047 Uiso 1 1 calc R U . . .
C23 C 0.67185(18) 0.46736(18) 0.69970(16) 0.0253(4) Uani 1 1 d . . . . .
H23 H 0.586472 0.475956 0.667501 0.030 Uiso 1 1 calc R U . . .
C24 C 0.7518(2) 0.4532(2) 0.6086(2) 0.0433(5) Uani 1 1 d . . . . .
H24A H 0.834078 0.442405 0.639637 0.065 Uiso 1 1 calc R U . . .
H24B H 0.782390 0.538735 0.596334 0.065 Uiso 1 1 calc R U . . .
H24C H 0.690554 0.369362 0.531167 0.065 Uiso 1 1 calc R U . . .
C25 C 0.7615(2) 0.5939(2) 0.8220(2) 0.0474(6) Uani 1 1 d . . . . .
H25A H 0.707576 0.596656 0.878870 0.071 Uiso 1 1 calc R U . . .
H25B H 0.789916 0.681826 0.813473 0.071 Uiso 1 1 calc R U . . .
H25C H 0.845262 0.585242 0.853021 0.071 Uiso 1 1 calc R U . . .
C8 C 0.61176(17) 0.10256(17) 0.78957(14) 0.0187(3) Uani 1 1 d . . . . .
C9 C 0.58498(18) 0.04682(19) 0.87078(16) 0.0249(4) Uani 1 1 d . . . . .
H9 H 0.490693 -0.002880 0.866432 0.030 Uiso 1 1 calc R U . . .
C10 C 0.69367(19) 0.0626(2) 0.95794(17) 0.0304(4) Uani 1 1 d . . . . .
H10 H 0.673414 0.023056 1.012103 0.036 Uiso 1 1 calc R U . . .
C11 C 0.83115(19) 0.1358(2) 0.96609(17) 0.0312(4) Uani 1 1 d . . . . .
H11 H 0.905776 0.148438 1.026823 0.037 Uiso 1 1 calc R U . . .
C12 C 0.85963(19) 0.1905(2) 0.88542(17) 0.0297(4) Uani 1 1 d . . . . .
H12 H 0.954181 0.240503 0.890537 0.036 Uiso 1 1 calc R U . . .
C13 C 0.75117(18) 0.17288(18) 0.79710(16) 0.0245(4) Uani 1 1 d . . . . .
H13 H 0.772018 0.209147 0.740988 0.029 Uiso 1 1 calc R U . . .
C2 C 0.31803(17) 0.02923(17) 0.72083(15) 0.0202(4) Uani 1 1 d . . . . .
C7 C 0.20954(18) -0.10879(19) 0.66435(17) 0.0285(4) Uani 1 1 d . . . . .
H7 H 0.216311 -0.181422 0.599593 0.034 Uiso 1 1 calc R U . . .
C6 C 0.09148(19) -0.1417(2) 0.7015(2) 0.0364(5) Uani 1 1 d . . . . .
H6 H 0.018893 -0.236623 0.662845 0.044 Uiso 1 1 calc R U . . .
C5 C 0.07934(19) -0.0376(2) 0.79365(19) 0.0336(5) Uani 1 1 d . . . . .
H5 H -0.002260 -0.060019 0.817885 0.040 Uiso 1 1 calc R U . . .
C4 C 0.18629(19) 0.1001(2) 0.85133(17) 0.0291(4) Uani 1 1 d . . . . .
H4 H 0.178449 0.172072 0.915880 0.035 Uiso 1 1 calc R U . . .
C3 C 0.30459(18) 0.13352(18) 0.81536(15) 0.0234(4) Uani 1 1 d . . . . .
H3 H 0.377414 0.228407 0.855431 0.028 Uiso 1 1 calc R U . . .
B1 B 0.34368(19) 0.34974(19) 0.66953(17) 0.0177(4) Uani 1 1 d . . . . .
O1 O 0.24516(12) 0.37801(12) 0.61391(10) 0.0224(3) Uani 1 1 d . . . . .
O2 O 0.39389(12) 0.42850(11) 0.79354(10) 0.0213(3) Uani 1 1 d . . . . .
C14 C 0.20318(18) 0.45851(18) 0.71064(15) 0.0224(4) Uani 1 1 d . . . . .
C15 C 0.33487(18) 0.53032(17) 0.82475(15) 0.0228(4) Uani 1 1 d . . . . .
C16 C 0.07383(19) 0.3504(2) 0.71593(18) 0.0309(4) Uani 1 1 d . . . . .
H16A H 0.001015 0.296503 0.636357 0.046 Uiso 1 1 calc R U . . .
H16B H 0.038655 0.400026 0.777019 0.046 Uiso 1 1 calc R U . . .
H16C H 0.098336 0.284736 0.737842 0.046 Uiso 1 1 calc R U . . .
C17 C 0.1679(2) 0.5623(2) 0.67813(19) 0.0358(5) Uani 1 1 d . . . . .
H17A H 0.247916 0.622113 0.662990 0.054 Uiso 1 1 calc R U . . .
H17B H 0.147304 0.622644 0.745453 0.054 Uiso 1 1 calc R U . . .
H17C H 0.085660 0.509080 0.604964 0.054 Uiso 1 1 calc R U . . .
C18 C 0.3029(2) 0.5465(2) 0.94195(16) 0.0339(5) Uani 1 1 d . . . . .
H18A H 0.238866 0.453014 0.931860 0.051 Uiso 1 1 calc R U . . .
H18B H 0.258730 0.610735 0.962372 0.051 Uiso 1 1 calc R U . . .
H18C H 0.390254 0.586114 1.007433 0.051 Uiso 1 1 calc R U . . .
C19 C 0.4459(2) 0.67087(19) 0.84199(19) 0.0365(5) Uani 1 1 d . . . . .
H19A H 0.532318 0.700923 0.904620 0.055 Uiso 1 1 calc R U . . .
H19B H 0.411970 0.743540 0.867153 0.055 Uiso 1 1 calc R U . . .
H19C H 0.464910 0.658803 0.765333 0.055 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
C1 N2 1.261(2) . ?
C1 N1 1.4306(19) . ?
C1 P1 1.8649(16) . ?
N1 B1 1.416(2) . ?
N1 C20 1.493(2) . ?
N2 C23 1.472(2) . ?
P1 C2 1.8309(17) . ?
P1 C8 1.8351(16) . ?
C20 C22 1.517(2) . ?
C20 C21 1.520(2) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C25 1.511(3) . ?
C23 C24 1.521(3) . ?
C23 H23 1.0000 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C8 C9 1.392(2) . ?
C8 C13 1.394(2) . ?
C9 C10 1.387(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C2 C7 1.392(2) . ?
C2 C3 1.395(2) . ?
C7 C6 1.389(3) . ?
C7 H7 0.9500 . ?
C6 C5 1.370(3) . ?
C6 H6 0.9500 . ?
C5 C4 1.384(3) . ?
C5 H5 0.9500 . ?
C4 C3 1.384(2) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
B1 O2 1.372(2) . ?
B1 O1 1.378(2) . ?
O1 C14 1.461(2) . ?
O2 C15 1.4617(19) . ?
C14 C17 1.518(2) . ?
C14 C16 1.518(2) . ?
C14 C15 1.562(2) . ?
C15 C18 1.515(2) . ?
C15 C19 1.520(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
N2 C1 N1 125.99(14) . . ?
N2 C1 P1 119.06(12) . . ?
N1 C1 P1 114.64(11) . . ?
B1 N1 C1 119.97(13) . . ?
B1 N1 C20 123.11(13) . . ?
C1 N1 C20 116.92(12) . . ?
C1 N2 C23 122.00(14) . . ?
C2 P1 C8 103.01(7) . . ?
C2 P1 C1 102.12(7) . . ?
C8 P1 C1 104.17(7) . . ?
N1 C20 C22 111.53(14) . . ?
N1 C20 C21 110.82(14) . . ?
C22 C20 C21 112.04(14) . . ?
N1 C20 H20 107.4 . . ?
C22 C20 H20 107.4 . . ?
C21 C20 H20 107.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 C25 108.67(15) . . ?
N2 C23 C24 106.72(15) . . ?
C25 C23 C24 112.08(17) . . ?
N2 C23 H23 109.8 . . ?
C25 C23 H23 109.8 . . ?
C24 C23 H23 109.8 . . ?
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 . . ?
C9 C8 C13 118.01(15) . . ?
C9 C8 P1 120.70(13) . . ?
C13 C8 P1 120.75(12) . . ?
C10 C9 C8 121.09(16) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 120.09(16) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.60(16) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.39(17) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.79(16) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C7 C2 C3 118.15(16) . . ?
C7 C2 P1 117.67(14) . . ?
C3 C2 P1 124.15(13) . . ?
C6 C7 C2 120.83(18) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
C5 C6 C7 120.26(18) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C5 C4 119.81(18) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C3 C4 C5 120.27(18) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C3 C2 120.68(16) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O2 B1 O1 113.49(15) . . ?
O2 B1 N1 122.66(15) . . ?
O1 B1 N1 123.83(15) . . ?
B1 O1 C14 105.96(12) . . ?
B1 O2 C15 107.11(12) . . ?
O1 C14 C17 108.63(14) . . ?
O1 C14 C16 106.43(13) . . ?
C17 C14 C16 110.35(15) . . ?
O1 C14 C15 102.61(12) . . ?
C17 C14 C15 114.52(15) . . ?
C16 C14 C15 113.60(14) . . ?
O2 C15 C18 108.16(14) . . ?
O2 C15 C19 106.99(14) . . ?
C18 C15 C19 110.49(15) . . ?
O2 C15 C14 102.12(12) . . ?
C18 C15 C14 114.82(15) . . ?
C19 C15 C14 113.50(15) . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
N2 C1 N1 B1 -63.1(2) . . . . ?
P1 C1 N1 B1 123.28(14) . . . . ?
N2 C1 N1 C20 116.87(18) . . . . ?
P1 C1 N1 C20 -56.73(16) . . . . ?
N1 C1 N2 C23 -5.9(3) . . . . ?
P1 C1 N2 C23 167.43(12) . . . . ?
N2 C1 P1 C2 132.40(14) . . . . ?
N1 C1 P1 C2 -53.52(13) . . . . ?
N2 C1 P1 C8 25.44(15) . . . . ?
N1 C1 P1 C8 -160.47(11) . . . . ?
B1 N1 C20 C22 -56.7(2) . . . . ?
C1 N1 C20 C22 123.34(15) . . . . ?
B1 N1 C20 C21 68.9(2) . . . . ?
C1 N1 C20 C21 -111.09(16) . . . . ?
C1 N2 C23 C25 133.51(18) . . . . ?
C1 N2 C23 C24 -105.44(19) . . . . ?
C2 P1 C8 C9 26.92(15) . . . . ?
C1 P1 C8 C9 133.21(14) . . . . ?
C2 P1 C8 C13 -161.63(13) . . . . ?
C1 P1 C8 C13 -55.34(15) . . . . ?
C13 C8 C9 C10 1.0(3) . . . . ?
P1 C8 C9 C10 172.70(14) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C8 1.4(3) . . . . ?
C9 C8 C13 C12 -2.0(3) . . . . ?
P1 C8 C13 C12 -173.71(14) . . . . ?
C8 P1 C2 C7 -112.79(13) . . . . ?
C1 P1 C2 C7 139.35(13) . . . . ?
C8 P1 C2 C3 68.80(14) . . . . ?
C1 P1 C2 C3 -39.06(15) . . . . ?
C3 C2 C7 C6 -0.2(2) . . . . ?
P1 C2 C7 C6 -178.72(13) . . . . ?
C2 C7 C6 C5 0.9(3) . . . . ?
C7 C6 C5 C4 -1.2(3) . . . . ?
C6 C5 C4 C3 0.7(3) . . . . ?
C5 C4 C3 C2 -0.1(2) . . . . ?
C7 C2 C3 C4 -0.2(2) . . . . ?
P1 C2 C3 C4 178.22(12) . . . . ?
C1 N1 B1 O2 -11.8(2) . . . . ?
C20 N1 B1 O2 168.21(15) . . . . ?
C1 N1 B1 O1 170.08(15) . . . . ?
C20 N1 B1 O1 -9.9(3) . . . . ?
O2 B1 O1 C14 -13.66(18) . . . . ?
N1 B1 O1 C14 164.61(16) . . . . ?
O1 B1 O2 C15 -6.14(18) . . . . ?
N1 B1 O2 C15 175.57(15) . . . . ?
B1 O1 C14 C17 147.54(15) . . . . ?
B1 O1 C14 C16 -93.65(15) . . . . ?
B1 O1 C14 C15 25.93(15) . . . . ?
B1 O2 C15 C18 143.11(15) . . . . ?
B1 O2 C15 C19 -97.86(16) . . . . ?
B1 O2 C15 C14 21.62(16) . . . . ?
O1 C14 C15 O2 -28.82(15) . . . . ?
C17 C14 C15 O2 -146.32(14) . . . . ?
C16 C14 C15 O2 85.63(16) . . . . ?
O1 C14 C15 C18 -145.60(14) . . . . ?
C17 C14 C15 C18 96.89(18) . . . . ?
C16 C14 C15 C18 -31.1(2) . . . . ?
O1 C14 C15 C19 85.96(16) . . . . ?
C17 C14 C15 C19 -31.5(2) . . . . ?
C16 C14 C15 C19 -159.58(15) . . . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.282
_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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1549901'
_audit_update_record             
;
2017-05-13 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 N O P'
_chemical_formula_sum            'C19 H22 N O P'
_chemical_formula_weight         311.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

_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'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, z+1/2'

_cell_length_a                   10.6648(7)
_cell_length_b                   34.271(2)
_cell_length_c                   9.4843(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3466.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      27.49

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.160
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'SADABS; Bruker, 2015'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12728
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.110
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_point_group_measured_fraction_full 0.879
_reflns_number_total             3235
_reflns_number_gt                2966
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.600
_reflns_Friedel_fraction_max     0.650
_reflns_Friedel_fraction_full    0.745

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0525P)²+4.3794P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1077 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3235
_refine_ls_number_parameters     203
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1301
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_restrained_S_all      1.202
_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
H1 H -0.034(5) 0.3736(16) 0.354(7) 0.077(19) Uiso 1 1 d . . . . .
C1 C 0.0358(3) 0.38523(11) 0.5388(4) 0.0327(8) Uani 1 1 d . . . . .
N1 N -0.0389(3) 0.36626(9) 0.4495(4) 0.0386(7) Uani 1 1 d . . . . .
O1 O 0.0445(3) 0.37671(8) 0.6634(3) 0.0468(8) Uani 1 1 d . . . . .
P1 P 0.12254(8) 0.42771(3) 0.45682(12) 0.0330(2) Uani 1 1 d . . . . .
C14 C -0.1103(3) 0.33171(11) 0.4915(4) 0.0346(9) Uani 1 1 d . . . . .
H14 H -0.148412 0.336731 0.586123 0.041 Uiso 1 1 calc R U . . .
C15 C -0.0250(4) 0.29602(11) 0.5029(5) 0.0435(10) Uani 1 1 d . . . . .
H15A H 0.040557 0.300842 0.574637 0.052 Uiso 1 1 calc R U . . .
H15B H 0.016901 0.291382 0.411248 0.052 Uiso 1 1 calc R U . . .
C16 C -0.1016(4) 0.25990(12) 0.5442(7) 0.0574(14) Uani 1 1 d . . . . .
H16A H -0.045879 0.236824 0.547735 0.069 Uiso 1 1 calc R U . . .
H13B H -0.137885 0.263745 0.639271 0.069 Uiso 1 1 calc R U . . .
C17 C -0.2066(4) 0.25262(13) 0.4387(8) 0.0619(15) Uani 1 1 d . . . . .
H17A H -0.170164 0.246559 0.345246 0.074 Uiso 1 1 calc R U . . .
H17B H -0.256831 0.229851 0.469384 0.074 Uiso 1 1 calc R U . . .
C18 C -0.2908(4) 0.28810(12) 0.4267(6) 0.0520(13) Uani 1 1 d . . . . .
H18A H -0.333598 0.292599 0.517951 0.062 Uiso 1 1 calc R U . . .
H18B H -0.355859 0.283259 0.354344 0.062 Uiso 1 1 calc R U . . .
C19 C -0.2154(4) 0.32447(13) 0.3867(5) 0.0435(10) Uani 1 1 d . . . . .
H19A H -0.179478 0.321013 0.291218 0.052 Uiso 1 1 calc R U . . .
H19B H -0.271758 0.347412 0.384343 0.052 Uiso 1 1 calc R U . . .
C8 C 0.2106(3) 0.44373(10) 0.6120(5) 0.0334(8) Uani 1 1 d . . . . .
C13 C 0.1411(4) 0.45895(11) 0.7233(5) 0.0399(9) Uani 1 1 d . . . . .
H13 H 0.052222 0.459924 0.716759 0.048 Uiso 1 1 calc R U . . .
C12 C 0.2002(4) 0.47271(11) 0.8436(5) 0.0449(10) Uani 1 1 d . . . . .
H12 H 0.151780 0.482347 0.920204 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3296(4) 0.47239(12) 0.8521(5) 0.0485(11) Uani 1 1 d . . . . .
H11 H 0.370604 0.482003 0.933915 0.058 Uiso 1 1 calc R U . . .
C10 C 0.3989(4) 0.45794(13) 0.7401(6) 0.0520(12) Uani 1 1 d . . . . .
H10 H 0.487832 0.457908 0.745095 0.062 Uiso 1 1 calc R U . . .
C9 C 0.3400(4) 0.44361(12) 0.6216(5) 0.0420(10) Uani 1 1 d . . . . .
H9 H 0.388713 0.433570 0.545982 0.050 Uiso 1 1 calc R U . . .
C2 C 0.2390(3) 0.40045(11) 0.3539(4) 0.0337(8) Uani 1 1 d . . . . .
C3 C 0.3016(4) 0.36781(11) 0.4063(5) 0.0412(9) Uani 1 1 d . . . . .
H3 H 0.282962 0.358411 0.498117 0.049 Uiso 1 1 calc R U . . .
C4 C 0.3910(4) 0.34905(13) 0.3248(6) 0.0490(11) Uani 1 1 d . . . . .
H4 H 0.433965 0.326941 0.361119 0.059 Uiso 1 1 calc R U . . .
C5 C 0.4178(4) 0.36259(13) 0.1900(6) 0.0528(13) Uani 1 1 d . . . . .
H5 H 0.479604 0.349824 0.134555 0.063 Uiso 1 1 calc R U . . .
C6 C 0.3550(4) 0.39444(14) 0.1366(5) 0.0520(12) Uani 1 1 d . . . . .
H6 H 0.373164 0.403501 0.044111 0.062 Uiso 1 1 calc R U . . .
C7 C 0.2649(4) 0.41338(13) 0.2181(5) 0.0402(9) Uani 1 1 d . . . . .
H7 H 0.221157 0.435193 0.180748 0.048 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
C1 O1 1.221(5) . ?
C1 N1 1.332(5) . ?
C1 P1 1.892(4) . ?
N1 C14 1.463(5) . ?
N1 H1 0.94(7) . ?
P1 C8 1.830(4) . ?
P1 C2 1.835(4) . ?
C14 C19 1.518(6) . ?
C14 C15 1.528(5) . ?
C14 H14 1.0000 . ?
C15 C16 1.534(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.522(8) . ?
C16 H16A 0.9900 . ?
C16 H13B 0.9900 . ?
C17 C18 1.516(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.531(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C8 C9 1.384(5) . ?
C8 C13 1.392(6) . ?
C13 C12 1.387(6) . ?
C13 H13 0.9500 . ?
C12 C11 1.383(6) . ?
C12 H12 0.9500 . ?
C11 C10 1.385(7) . ?
C11 H11 0.9500 . ?
C10 C9 1.378(6) . ?
C10 H10 0.9500 . ?
C9 H9 0.9500 . ?
C2 C7 1.390(6) . ?
C2 C3 1.395(5) . ?
C3 C4 1.385(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(6) . ?
C6 H6 0.9500 . ?
C7 H7 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
O1 C1 N1 123.0(4) . . ?
O1 C1 P1 123.0(3) . . ?
N1 C1 P1 114.0(3) . . ?
C1 N1 C14 122.2(4) . . ?
C1 N1 H1 117(4) . . ?
C14 N1 H1 120(4) . . ?
C8 P1 C2 103.50(17) . . ?
C8 P1 C1 98.71(17) . . ?
C2 P1 C1 99.07(17) . . ?
N1 C14 C19 109.8(3) . . ?
N1 C14 C15 110.9(3) . . ?
C19 C14 C15 110.8(3) . . ?
N1 C14 H14 108.4 . . ?
C19 C14 H14 108.4 . . ?
C15 C14 H14 108.4 . . ?
C14 C15 C16 110.3(3) . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 110.9(4) . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H13B 109.5 . . ?
C15 C16 H13B 109.5 . . ?
H16A C16 H13B 108.1 . . ?
C18 C17 C16 110.7(4) . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 C19 111.1(3) . . ?
C17 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C14 C19 C18 111.0(4) . . ?
C14 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
C14 C19 H19B 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C9 C8 C13 118.9(4) . . ?
C9 C8 P1 124.4(3) . . ?
C13 C8 P1 116.7(3) . . ?
C12 C13 C8 120.7(4) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C11 C12 C13 119.9(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C11 C10 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C9 C10 C11 120.7(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C7 C2 C3 119.4(4) . . ?
C7 C2 P1 117.7(3) . . ?
C3 C2 P1 122.9(3) . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.0(4) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 120.2(4) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?

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
O1 C1 N1 C14 -4.5(6) . . . . ?
P1 C1 N1 C14 177.7(3) . . . . ?
O1 C1 P1 C8 2.7(4) . . . . ?
N1 C1 P1 C8 -179.4(3) . . . . ?
O1 C1 P1 C2 108.0(4) . . . . ?
N1 C1 P1 C2 -74.2(3) . . . . ?
C1 N1 C14 C19 162.0(3) . . . . ?
C1 N1 C14 C15 -75.3(5) . . . . ?
N1 C14 C15 C16 -178.9(4) . . . . ?
C19 C14 C15 C16 -56.8(5) . . . . ?
C14 C15 C16 C17 57.1(5) . . . . ?
C15 C16 C17 C18 -56.9(6) . . . . ?
C16 C17 C18 C19 56.3(6) . . . . ?
N1 C14 C19 C18 179.2(3) . . . . ?
C15 C14 C19 C18 56.4(4) . . . . ?
C17 C18 C19 C14 -56.2(6) . . . . ?
C2 P1 C8 C9 15.6(4) . . . . ?
C1 P1 C8 C9 117.2(3) . . . . ?
C2 P1 C8 C13 -168.1(3) . . . . ?
C1 P1 C8 C13 -66.5(3) . . . . ?
C9 C8 C13 C12 -1.9(6) . . . . ?
P1 C8 C13 C12 -178.4(3) . . . . ?
C8 C13 C12 C11 1.8(6) . . . . ?
C13 C12 C11 C10 -0.6(7) . . . . ?
C12 C11 C10 C9 -0.6(7) . . . . ?
C11 C10 C9 C8 0.6(7) . . . . ?
C13 C8 C9 C10 0.7(6) . . . . ?
P1 C8 C9 C10 176.9(4) . . . . ?
C8 P1 C2 C7 -120.6(3) . . . . ?
C1 P1 C2 C7 138.1(3) . . . . ?
C8 P1 C2 C3 59.2(3) . . . . ?
C1 P1 C2 C3 -42.1(4) . . . . ?
C7 C2 C3 C4 1.5(6) . . . . ?
P1 C2 C3 C4 -178.3(3) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C4 C5 C6 C7 0.4(6) . . . . ?
C3 C2 C7 C6 -1.6(6) . . . . ?
P1 C2 C7 C6 178.2(3) . . . . ?
C5 C6 C7 C2 0.6(6) . . . . ?

_refine_diff_density_max         0.788
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1549904'
_audit_update_record             
;
2017-05-13 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H27 B N O3 P'
_chemical_formula_sum            'C21 H27 B N O3 P'
_chemical_formula_weight         383.21

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'
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                   6.2343(10)
_cell_length_b                   9.4532(13)
_cell_length_c                   17.992(3)
_cell_angle_alpha                86.725(5)
_cell_angle_beta                 89.957(6)
_cell_angle_gamma                84.737(5)
_cell_volume                     1054.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9863
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      33.19

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.607
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.087
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   0.914
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS; Bruker, 2015'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45511
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.046
_diffrn_reflns_theta_max         29.999
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6150
_reflns_number_gt                5216
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0384P)²+0.4300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6150
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0881
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
C1 C 0.32798(19) 0.35747(11) 0.29524(6) 0.0220(2) Uani 1 1 d . . . . .
O1 O 0.2877(2) 0.23389(9) 0.30013(6) 0.0435(3) Uani 1 1 d . . . . .
P1 P 0.50246(5) 0.42146(3) 0.21638(2) 0.01930(7) Uani 1 1 d . . . . .
N1 N 0.25936(15) 0.44963(9) 0.34913(5) 0.01888(18) Uani 1 1 d . . . . .
B1 B 0.3054(2) 0.59608(12) 0.35152(7) 0.0188(2) Uani 1 1 d . . . . .
O11 O 0.43682(13) 0.66164(8) 0.30311(4) 0.02110(16) Uani 1 1 d . . . . .
O12 O 0.21636(14) 0.68044(8) 0.40492(5) 0.02581(18) Uani 1 1 d . . . . .
C20 C 0.12151(19) 0.39208(12) 0.40860(6) 0.0232(2) Uani 1 1 d . . . . .
H20A H 0.134186 0.446293 0.453621 0.028 Uiso 1 1 calc R U . . .
H20B H 0.173506 0.291600 0.421562 0.028 Uiso 1 1 calc R U . . .
C21 C -0.1120(2) 0.4002(2) 0.38549(9) 0.0472(4) Uani 1 1 d . . . . .
H21A H -0.161195 0.498410 0.368940 0.071 Uiso 1 1 calc R U . . .
H21B H -0.198833 0.369895 0.427902 0.071 Uiso 1 1 calc R U . . .
H21C H -0.127721 0.337690 0.344615 0.071 Uiso 1 1 calc R U . . .
C2 C 0.30312(18) 0.52728(11) 0.15615(6) 0.0197(2) Uani 1 1 d . . . . .
C3 C 0.08786(19) 0.56101(13) 0.17380(7) 0.0255(2) Uani 1 1 d . . . . .
H3 H 0.032772 0.525639 0.219752 0.031 Uiso 1 1 calc R U . . .
C4 C -0.0473(2) 0.64618(15) 0.12463(8) 0.0338(3) Uani 1 1 d . . . . .
H4 H -0.193516 0.669784 0.137522 0.041 Uiso 1 1 calc R U . . .
C5 C 0.0301(3) 0.69661(16) 0.05711(8) 0.0396(3) Uani 1 1 d . . . . .
H5 H -0.062839 0.754325 0.023556 0.048 Uiso 1 1 calc R U . . .
C6 C 0.2435(3) 0.66270(15) 0.03854(7) 0.0385(3) Uani 1 1 d . . . . .
H6 H 0.296977 0.696564 -0.007964 0.046 Uiso 1 1 calc R U . . .
C7 C 0.3789(2) 0.57939(13) 0.08782(7) 0.0289(3) Uani 1 1 d . . . . .
H7 H 0.525444 0.557381 0.074943 0.035 Uiso 1 1 calc R U . . .
C8 C 0.53412(18) 0.25631(12) 0.16759(6) 0.0211(2) Uani 1 1 d . . . . .
C9 C 0.3686(2) 0.20121(13) 0.12941(6) 0.0257(2) Uani 1 1 d . . . . .
H9 H 0.228688 0.250435 0.127788 0.031 Uiso 1 1 calc R U . . .
C10 C 0.4071(2) 0.07516(13) 0.09384(7) 0.0306(3) Uani 1 1 d . . . . .
H10 H 0.293309 0.038020 0.068267 0.037 Uiso 1 1 calc R U . . .
C11 C 0.6112(2) 0.00317(13) 0.09550(7) 0.0334(3) Uani 1 1 d . . . . .
H11 H 0.636813 -0.083302 0.071151 0.040 Uiso 1 1 calc R U . . .
C12 C 0.7768(2) 0.05659(14) 0.13230(7) 0.0340(3) Uani 1 1 d . . . . .
H12 H 0.916654 0.007257 0.133090 0.041 Uiso 1 1 calc R U . . .
C13 C 0.7394(2) 0.18308(13) 0.16843(7) 0.0274(2) Uani 1 1 d . . . . .
H13 H 0.854066 0.219701 0.193753 0.033 Uiso 1 1 calc R U . . .
C14 C 0.40332(19) 0.81418(11) 0.31599(6) 0.0219(2) Uani 1 1 d . . . . .
C15 C 0.32526(19) 0.81160(12) 0.39827(7) 0.0243(2) Uani 1 1 d . . . . .
C16 C 0.6152(2) 0.87722(15) 0.30275(8) 0.0347(3) Uani 1 1 d . . . . .
H16A H 0.726828 0.824949 0.334512 0.052 Uiso 1 1 calc R U . . .
H16B H 0.600138 0.977444 0.314779 0.052 Uiso 1 1 calc R U . . .
H16C H 0.655935 0.870136 0.250390 0.052 Uiso 1 1 calc R U . . .
C17 C 0.2341(2) 0.87909(13) 0.26043(8) 0.0322(3) Uani 1 1 d . . . . .
H17A H 0.280449 0.857665 0.209917 0.048 Uiso 1 1 calc R U . . .
H17B H 0.215549 0.982446 0.264428 0.048 Uiso 1 1 calc R U . . .
H17C H 0.097052 0.839107 0.271060 0.048 Uiso 1 1 calc R U . . .
C18 C 0.5092(2) 0.79345(16) 0.45452(7) 0.0373(3) Uani 1 1 d . . . . .
H18A H 0.451638 0.775273 0.504507 0.056 Uiso 1 1 calc R U . . .
H18B H 0.583868 0.880387 0.453276 0.056 Uiso 1 1 calc R U . . .
H18C H 0.610733 0.712990 0.442023 0.056 Uiso 1 1 calc R U . . .
C19 C 0.1655(2) 0.93507(14) 0.41641(9) 0.0386(3) Uani 1 1 d . . . . .
H19A H 0.036619 0.935120 0.385234 0.058 Uiso 1 1 calc R U . . .
H19B H 0.231070 1.024597 0.406747 0.058 Uiso 1 1 calc R U . . .
H19C H 0.125229 0.925429 0.468998 0.058 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
C1 O1 1.2156(14) . ?
C1 N1 1.3820(13) . ?
C1 P1 1.8927(12) . ?
P1 C8 1.8295(11) . ?
P1 C2 1.8356(11) . ?
N1 B1 1.4424(14) . ?
N1 C20 1.4822(13) . ?
B1 O11 1.3579(14) . ?
B1 O12 1.3686(14) . ?
O11 C14 1.4694(13) . ?
O12 C15 1.4662(13) . ?
C20 C21 1.5082(19) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C2 C3 1.3914(16) . ?
C2 C7 1.3962(15) . ?
C3 C4 1.3916(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.3849(18) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.3958(17) . ?
C8 C13 1.3976(16) . ?
C9 C10 1.3862(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.3864(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3944(18) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C16 1.5113(17) . ?
C14 C17 1.5169(17) . ?
C14 C15 1.5576(16) . ?
C15 C19 1.5137(17) . ?
C15 C18 1.5217(19) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 120.78(10) . . ?
O1 C1 P1 119.63(9) . . ?
N1 C1 P1 119.46(8) . . ?
C8 P1 C2 100.51(5) . . ?
C8 P1 C1 97.73(5) . . ?
C2 P1 C1 101.69(5) . . ?
C1 N1 B1 126.03(9) . . ?
C1 N1 C20 116.25(9) . . ?
B1 N1 C20 117.71(9) . . ?
O11 B1 O12 114.60(9) . . ?
O11 B1 N1 124.48(10) . . ?
O12 B1 N1 120.92(10) . . ?
B1 O11 C14 106.12(8) . . ?
B1 O12 C15 105.80(8) . . ?
N1 C20 C21 112.29(10) . . ?
N1 C20 H20A 109.1 . . ?
C21 C20 H20A 109.1 . . ?
N1 C20 H20B 109.1 . . ?
C21 C20 H20B 109.1 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C2 C7 118.46(10) . . ?
C3 C2 P1 125.48(8) . . ?
C7 C2 P1 116.05(9) . . ?
C2 C3 C4 120.49(11) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.32(12) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.78(12) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 119.96(12) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 120.99(12) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
C9 C8 C13 118.80(11) . . ?
C9 C8 P1 124.30(8) . . ?
C13 C8 P1 116.90(9) . . ?
C10 C9 C8 120.45(11) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.14(13) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.22(11) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.02(12) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 120.37(12) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
O11 C14 C16 107.83(10) . . ?
O11 C14 C17 106.90(9) . . ?
C16 C14 C17 110.85(10) . . ?
O11 C14 C15 101.77(8) . . ?
C16 C14 C15 114.79(10) . . ?
C17 C14 C15 113.81(10) . . ?
O12 C15 C19 108.56(10) . . ?
O12 C15 C18 106.61(10) . . ?
C19 C15 C18 110.60(11) . . ?
O12 C15 C14 102.36(8) . . ?
C19 C15 C14 114.74(11) . . ?
C18 C15 C14 113.22(10) . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O1 C1 P1 C8 4.06(12) . . . . ?
N1 C1 P1 C8 180.00(9) . . . . ?
O1 C1 P1 C2 106.54(11) . . . . ?
N1 C1 P1 C2 -77.53(10) . . . . ?
O1 C1 N1 B1 176.85(12) . . . . ?
P1 C1 N1 B1 0.96(15) . . . . ?
O1 C1 N1 C20 -4.72(17) . . . . ?
P1 C1 N1 C20 179.40(8) . . . . ?
C1 N1 B1 O11 -4.79(18) . . . . ?
C20 N1 B1 O11 176.80(10) . . . . ?
C1 N1 B1 O12 175.42(11) . . . . ?
C20 N1 B1 O12 -2.99(16) . . . . ?
O12 B1 O11 C14 -11.44(13) . . . . ?
N1 B1 O11 C14 168.75(10) . . . . ?
O11 B1 O12 C15 -9.12(13) . . . . ?
N1 B1 O12 C15 170.69(10) . . . . ?
C1 N1 C20 C21 -83.38(14) . . . . ?
B1 N1 C20 C21 95.19(13) . . . . ?
C8 P1 C2 C3 107.64(10) . . . . ?
C1 P1 C2 C3 7.38(11) . . . . ?
C8 P1 C2 C7 -73.70(10) . . . . ?
C1 P1 C2 C7 -173.96(9) . . . . ?
C7 C2 C3 C4 -0.75(18) . . . . ?
P1 C2 C3 C4 177.88(10) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C5 C6 C7 C2 0.7(2) . . . . ?
C3 C2 C7 C6 -0.04(19) . . . . ?
P1 C2 C7 C6 -178.80(11) . . . . ?
C2 P1 C8 C9 -33.86(11) . . . . ?
C1 P1 C8 C9 69.62(10) . . . . ?
C2 P1 C8 C13 145.25(9) . . . . ?
C1 P1 C8 C13 -111.27(9) . . . . ?
C13 C8 C9 C10 0.83(17) . . . . ?
P1 C8 C9 C10 179.92(9) . . . . ?
C8 C9 C10 C11 -0.45(18) . . . . ?
C9 C10 C11 C12 -0.15(19) . . . . ?
C10 C11 C12 C13 0.35(19) . . . . ?
C11 C12 C13 C8 0.04(19) . . . . ?
C9 C8 C13 C12 -0.63(17) . . . . ?
P1 C8 C13 C12 -179.79(9) . . . . ?
B1 O11 C14 C16 146.49(10) . . . . ?
B1 O11 C14 C17 -94.26(11) . . . . ?
B1 O11 C14 C15 25.36(11) . . . . ?
B1 O12 C15 C19 145.85(11) . . . . ?
B1 O12 C15 C18 -94.97(11) . . . . ?
B1 O12 C15 C14 24.15(12) . . . . ?
O11 C14 C15 O12 -29.96(11) . . . . ?
C16 C14 C15 O12 -146.11(10) . . . . ?
C17 C14 C15 O12 84.66(11) . . . . ?
O11 C14 C15 C19 -147.34(10) . . . . ?
C16 C14 C15 C19 96.51(13) . . . . ?
C17 C14 C15 C19 -32.72(14) . . . . ?
O11 C14 C15 C18 84.40(11) . . . . ?
C16 C14 C15 C18 -31.75(14) . . . . ?
C17 C14 C15 C18 -160.98(10) . . . . ?

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
C17 H17B O1 0.98 2.58 3.5143(16) 160.3 1_565

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.259
_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_platon_sq
_database_code_depnum_ccdc_archive 'CCDC 1549902'
_audit_update_record             
;
2017-07-10 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H31 B N O3 P'
_chemical_formula_sum            'C23 H31 B N O3 P'
_chemical_formula_weight         411.27

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'
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                   9.5854(7)
_cell_length_b                   9.7989(8)
_cell_length_c                   15.9177(14)
_cell_angle_alpha                75.187(3)
_cell_angle_beta                 80.891(3)
_cell_angle_gamma                63.041(3)
_cell_volume                     1286.77(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9060
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      29.95

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.061
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.611
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   'SADABS; Bruker, 2015'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            65255
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.174
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7499
_reflns_number_gt                6126
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+0.5260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7499
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
C1 C 0.97738(12) 0.94362(13) 0.26555(7) 0.0200(2) Uani 1 1 d . . . . .
C20 C 0.78633(14) 1.16913(16) 0.32937(10) 0.0327(3) Uani 1 1 d . . . . .
C21 C 0.61029(17) 1.2414(2) 0.35243(14) 0.0523(5) Uani 1 1 d . . . . .
H21A H 0.552612 1.278467 0.299347 0.078 Uiso 1 1 calc R U . . .
H21B H 0.582834 1.329647 0.379973 0.078 Uiso 1 1 calc R U . . .
H21C H 0.582565 1.162379 0.392748 0.078 Uiso 1 1 calc R U . . .
C22 C 0.8257(2) 1.29078(18) 0.26394(16) 0.0592(5) Uani 1 1 d . . . . .
H22A H 0.939037 1.247440 0.250677 0.089 Uiso 1 1 calc R U . . .
H22B H 0.792290 1.383739 0.288352 0.089 Uiso 1 1 calc R U . . .
H22C H 0.771157 1.319836 0.210478 0.089 Uiso 1 1 calc R U . . .
C23 C 0.8741(2) 1.1127(3) 0.41276(13) 0.0559(5) Uani 1 1 d . . . . .
H23A H 0.846516 1.033383 0.452827 0.084 Uiso 1 1 calc R U . . .
H23B H 0.844977 1.201398 0.440231 0.084 Uiso 1 1 calc R U . . .
H23C H 0.987260 1.067057 0.398723 0.084 Uiso 1 1 calc R U . . .
C8 C 1.17226(14) 0.74123(14) 0.15435(8) 0.0236(2) Uani 1 1 d . . . . .
C13 C 1.15366(17) 0.85802(17) 0.07965(9) 0.0338(3) Uani 1 1 d . . . . .
H13 H 1.057669 0.950202 0.072412 0.041 Uiso 1 1 calc R U . . .
C12 C 1.2732(2) 0.8416(2) 0.01573(9) 0.0417(3) Uani 1 1 d . . . . .
H12 H 1.258993 0.922189 -0.034860 0.050 Uiso 1 1 calc R U . . .
C11 C 1.4127(2) 0.7083(2) 0.02569(10) 0.0447(4) Uani 1 1 d . . . . .
H11 H 1.494456 0.696332 -0.018285 0.054 Uiso 1 1 calc R U . . .
C10 C 1.43361(19) 0.5922(2) 0.09951(11) 0.0450(4) Uani 1 1 d . . . . .
H10 H 1.530395 0.500966 0.106555 0.054 Uiso 1 1 calc R U . . .
C9 C 1.31392(16) 0.60779(16) 0.16382(9) 0.0337(3) Uani 1 1 d . . . . .
H9 H 1.329114 0.526915 0.214343 0.040 Uiso 1 1 calc R U . . .
C2 C 1.08653(13) 0.61574(13) 0.32659(8) 0.0233(2) Uani 1 1 d . . . . .
C3 C 1.18207(16) 0.62301(16) 0.38113(9) 0.0329(3) Uani 1 1 d . . . . .
H3 H 1.205969 0.710397 0.369141 0.039 Uiso 1 1 calc R U . . .
C4 C 1.24257(19) 0.50313(19) 0.45295(10) 0.0418(3) Uani 1 1 d . . . . .
H4 H 1.307314 0.509375 0.489872 0.050 Uiso 1 1 calc R U . . .
C5 C 1.20959(18) 0.37510(17) 0.47122(10) 0.0420(4) Uani 1 1 d . . . . .
H5 H 1.251037 0.293645 0.520562 0.050 Uiso 1 1 calc R U . . .
C6 C 1.11636(19) 0.36628(17) 0.41752(11) 0.0421(4) Uani 1 1 d . . . . .
H6 H 1.094342 0.277728 0.429492 0.051 Uiso 1 1 calc R U . . .
C7 C 1.05384(16) 0.48618(15) 0.34564(9) 0.0325(3) Uani 1 1 d . . . . .
H7 H 0.988424 0.479452 0.309363 0.039 Uiso 1 1 calc R U . . .
C14 C 0.52483(14) 0.88643(14) 0.30752(8) 0.0240(2) Uani 1 1 d . . . . .
C15 C 0.48333(13) 1.01544(15) 0.22116(8) 0.0253(2) Uani 1 1 d . . . . .
C16 C 0.5938(2) 0.71996(18) 0.29291(12) 0.0481(4) Uani 1 1 d . . . . .
H16A H 0.678989 0.705196 0.247943 0.072 Uiso 1 1 calc R U . . .
H16B H 0.512098 0.702022 0.274112 0.072 Uiso 1 1 calc R U . . .
H16C H 0.634838 0.645548 0.347286 0.072 Uiso 1 1 calc R U . . .
C17 C 0.39480(18) 0.9103(2) 0.37763(10) 0.0468(4) Uani 1 1 d . . . . .
H17A H 0.431122 0.824102 0.428368 0.070 Uiso 1 1 calc R U . . .
H17B H 0.303879 0.912559 0.355458 0.070 Uiso 1 1 calc R U . . .
H17C H 0.365054 1.009686 0.394545 0.070 Uiso 1 1 calc R U . . .
C18 C 0.4706(2) 0.9614(2) 0.14396(11) 0.0482(4) Uani 1 1 d . . . . .
H18A H 0.444425 1.048427 0.093242 0.072 Uiso 1 1 calc R U . . .
H18B H 0.388204 0.924929 0.156286 0.072 Uiso 1 1 calc R U . . .
H18C H 0.570808 0.875375 0.131859 0.072 Uiso 1 1 calc R U . . .
C19 C 0.33752(17) 1.16483(18) 0.23187(13) 0.0458(4) Uani 1 1 d . . . . .
H19A H 0.347184 1.200540 0.281896 0.069 Uiso 1 1 calc R U . . .
H19B H 0.244873 1.143878 0.241445 0.069 Uiso 1 1 calc R U . . .
H19C H 0.326727 1.246128 0.179156 0.069 Uiso 1 1 calc R U . . .
B1 B 0.69955(14) 0.99265(14) 0.27719(8) 0.0187(2) Uani 1 1 d . . . . .
N1 N 0.82666(10) 1.03107(11) 0.28987(6) 0.01967(18) Uani 1 1 d . . . . .
O1 O 1.08769(10) 0.97346(11) 0.26717(6) 0.0294(2) Uani 1 1 d . . . . .
O11 O 0.65137(10) 0.89928(10) 0.34050(6) 0.02543(18) Uani 1 1 d . . . . .
O12 O 0.61449(10) 1.05799(10) 0.20534(5) 0.02535(18) Uani 1 1 d . . . . .
P1 P 1.00260(3) 0.76414(3) 0.22944(2) 0.02141(8) 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
C1 O1 1.2235(13) . ?
C1 N1 1.3570(14) . ?
C1 P1 1.8894(11) . ?
C20 N1 1.5030(15) . ?
C20 C22 1.515(2) . ?
C20 C23 1.527(2) . ?
C20 C21 1.5287(19) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C8 C9 1.3894(17) . ?
C8 C13 1.3935(18) . ?
C8 P1 1.8205(12) . ?
C13 C12 1.386(2) . ?
C13 H13 0.9500 . ?
C12 C11 1.377(2) . ?
C12 H12 0.9500 . ?
C11 C10 1.378(2) . ?
C11 H11 0.9500 . ?
C10 C9 1.3917(19) . ?
C10 H10 0.9500 . ?
C9 H9 0.9500 . ?
C2 C7 1.3912(17) . ?
C2 C3 1.3929(18) . ?
C2 P1 1.8266(12) . ?
C3 C4 1.3888(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C14 O11 1.4618(13) . ?
C14 C17 1.5108(18) . ?
C14 C16 1.5229(19) . ?
C14 C15 1.5731(17) . ?
C15 O12 1.4626(13) . ?
C15 C18 1.4983(19) . ?
C15 C19 1.5239(19) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
B1 O11 1.3528(14) . ?
B1 O12 1.3529(14) . ?
B1 N1 1.4830(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 125.09(10) . . ?
O1 C1 P1 122.27(8) . . ?
N1 C1 P1 112.63(8) . . ?
N1 C20 C22 109.68(13) . . ?
N1 C20 C23 108.99(12) . . ?
C22 C20 C23 112.13(14) . . ?
N1 C20 C21 108.59(10) . . ?
C22 C20 C21 108.68(14) . . ?
C23 C20 C21 108.71(14) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C9 C8 C13 118.57(12) . . ?
C9 C8 P1 123.39(10) . . ?
C13 C8 P1 117.78(10) . . ?
C12 C13 C8 120.94(13) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C11 C12 C13 119.89(14) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C11 C10 119.93(14) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C10 C9 120.47(14) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C8 C9 C10 120.20(13) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C7 C2 C3 118.57(12) . . ?
C7 C2 P1 117.00(10) . . ?
C3 C2 P1 124.42(9) . . ?
C4 C3 C2 120.32(13) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.66(15) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 119.49(13) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 120.50(14) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 120.46(14) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
O11 C14 C17 107.42(10) . . ?
O11 C14 C16 105.65(11) . . ?
C17 C14 C16 110.08(13) . . ?
O11 C14 C15 103.69(8) . . ?
C17 C14 C15 115.41(11) . . ?
C16 C14 C15 113.72(11) . . ?
O12 C15 C18 109.37(11) . . ?
O12 C15 C19 105.78(10) . . ?
C18 C15 C19 109.82(13) . . ?
O12 C15 C14 103.39(8) . . ?
C18 C15 C14 114.74(11) . . ?
C19 C15 C14 113.12(11) . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O11 B1 O12 114.93(10) . . ?
O11 B1 N1 121.84(10) . . ?
O12 B1 N1 122.98(10) . . ?
C1 N1 B1 120.55(9) . . ?
C1 N1 C20 120.30(9) . . ?
B1 N1 C20 119.15(9) . . ?
B1 O11 C14 108.00(9) . . ?
B1 O12 C15 108.19(9) . . ?
C8 P1 C2 103.32(5) . . ?
C8 P1 C1 98.87(5) . . ?
C2 P1 C1 99.45(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
C9 C8 C13 C12 0.4(2) . . . . ?
P1 C8 C13 C12 -173.99(11) . . . . ?
C8 C13 C12 C11 0.0(2) . . . . ?
C13 C12 C11 C10 -0.6(2) . . . . ?
C12 C11 C10 C9 0.8(3) . . . . ?
C13 C8 C9 C10 -0.2(2) . . . . ?
P1 C8 C9 C10 173.82(12) . . . . ?
C11 C10 C9 C8 -0.4(2) . . . . ?
C7 C2 C3 C4 -0.1(2) . . . . ?
P1 C2 C3 C4 -179.00(11) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C7 -0.7(2) . . . . ?
C3 C2 C7 C6 -0.35(19) . . . . ?
P1 C2 C7 C6 178.58(10) . . . . ?
C5 C6 C7 C2 0.8(2) . . . . ?
O11 C14 C15 O12 13.19(12) . . . . ?
C17 C14 C15 O12 130.36(12) . . . . ?
C16 C14 C15 O12 -101.03(12) . . . . ?
O11 C14 C15 C18 132.20(12) . . . . ?
C17 C14 C15 C18 -110.62(15) . . . . ?
C16 C14 C15 C18 17.99(16) . . . . ?
O11 C14 C15 C19 -100.74(12) . . . . ?
C17 C14 C15 C19 16.44(16) . . . . ?
C16 C14 C15 C19 145.05(13) . . . . ?
O1 C1 N1 B1 174.00(11) . . . . ?
P1 C1 N1 B1 -6.91(13) . . . . ?
O1 C1 N1 C20 -5.49(18) . . . . ?
P1 C1 N1 C20 173.60(9) . . . . ?
O11 B1 N1 C1 93.08(14) . . . . ?
O12 B1 N1 C1 -92.77(14) . . . . ?
O11 B1 N1 C20 -87.42(14) . . . . ?
O12 B1 N1 C20 86.72(14) . . . . ?
C22 C20 N1 C1 62.99(15) . . . . ?
C23 C20 N1 C1 -60.11(16) . . . . ?
C21 C20 N1 C1 -178.37(13) . . . . ?
C22 C20 N1 B1 -116.50(13) . . . . ?
C23 C20 N1 B1 120.39(13) . . . . ?
C21 C20 N1 B1 2.13(17) . . . . ?
O12 B1 O11 C14 4.92(14) . . . . ?
N1 B1 O11 C14 179.51(10) . . . . ?
C17 C14 O11 B1 -133.81(12) . . . . ?
C16 C14 O11 B1 108.70(12) . . . . ?
C15 C14 O11 B1 -11.18(12) . . . . ?
O11 B1 O12 C15 4.37(14) . . . . ?
N1 B1 O12 C15 -170.15(10) . . . . ?
C18 C15 O12 B1 -133.51(12) . . . . ?
C19 C15 O12 B1 108.27(12) . . . . ?
C14 C15 O12 B1 -10.85(12) . . . . ?
C9 C8 P1 C2 18.52(12) . . . . ?
C13 C8 P1 C2 -167.43(10) . . . . ?
C9 C8 P1 C1 120.51(11) . . . . ?
C13 C8 P1 C1 -65.44(11) . . . . ?
C7 C2 P1 C8 -109.10(10) . . . . ?
C3 C2 P1 C8 69.77(12) . . . . ?
C7 C2 P1 C1 149.37(10) . . . . ?
C3 C2 P1 C1 -31.77(12) . . . . ?
O1 C1 P1 C8 -28.83(11) . . . . ?
N1 C1 P1 C8 152.05(8) . . . . ?
O1 C1 P1 C2 76.38(11) . . . . ?
N1 C1 P1 C2 -102.74(9) . . . . ?

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
_geom_hbond_publ_flag
C21 H21C O11 0.98 2.67 3.2456(19) 117.5 . yes
C22 H22A O1 0.98 2.37 2.9761(19) 119.7 . yes
C23 H23C O1 0.98 2.39 3.0007(19) 120.1 . yes
C3 H3 O1 0.95 2.52 3.2278(17) 131.2 . yes
C17 H17B O1 0.98 2.45 3.4015(18) 164.0 1_455 yes
C19 H19B O1 0.98 2.64 3.5599(18) 156.7 1_455 yes

_refine_diff_density_max         0.557
_refine_diff_density_min         -0.391
_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_p-1
_database_code_depnum_ccdc_archive 'CCDC 1549903'
_audit_update_record             
;
2017-07-10 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H31 B N O2 P S'
_chemical_formula_sum            'C23 H31 B N O2 P S'
_chemical_formula_weight         427.33

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'
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      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                   10.3603(12)
_cell_length_b                   17.1280(19)
_cell_length_c                   26.966(3)
_cell_angle_alpha                92.761(4)
_cell_angle_beta                 93.308(4)
_cell_angle_gamma                90.282(4)
_cell_volume                     4771.5(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9330
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      29.61

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.724
_exptl_crystal_size_mid          0.341
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.221
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'SADABS; Bruker,2015'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            213108
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.780
_diffrn_reflns_theta_max         29.709
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             26943
_reflns_number_gt                23251
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0479P)²+6.0451P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         26943
_refine_ls_number_parameters     1111
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1507
_refine_ls_wR_factor_gt          0.1444
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.096
_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
C11 C 0.36124(18) 0.13936(11) 0.11434(7) 0.0226(3) Uani 1 1 d . . . . .
P1 P 0.32132(4) 0.03809(3) 0.13278(2) 0.02055(9) Uani 1 1 d . . . . .
S1 S 0.50950(5) 0.16339(3) 0.10042(2) 0.03521(12) Uani 1 1 d . . . . .
N1 N 0.25595(16) 0.18458(9) 0.11521(6) 0.0241(3) Uani 1 1 d . . . . .
B1 B 0.1262(2) 0.14689(12) 0.11721(8) 0.0220(4) Uani 1 1 d . . . . .
O11 O 0.06761(13) 0.13607(9) 0.16013(5) 0.0268(3) Uani 1 1 d . . . . .
O12 O 0.05353(13) 0.12673(9) 0.07485(5) 0.0250(3) Uani 1 1 d . . . . .
C12 C 0.36638(18) 0.04630(11) 0.19932(7) 0.0219(3) Uani 1 1 d . . . . .
C13 C 0.4532(2) 0.10081(13) 0.22197(8) 0.0337(5) Uani 1 1 d . . . . .
H13 H 0.495128 0.136712 0.202328 0.040 Uiso 1 1 calc R U . . .
C14 C 0.4793(3) 0.10327(15) 0.27316(9) 0.0409(6) Uani 1 1 d . . . . .
H14 H 0.537351 0.141580 0.288399 0.049 Uiso 1 1 calc R U . . .
C15 C 0.4216(2) 0.05053(17) 0.30181(8) 0.0411(6) Uani 1 1 d . . . . .
H15 H 0.440687 0.052037 0.336724 0.049 Uiso 1 1 calc R U . . .
C16 C 0.3359(2) -0.00459(18) 0.28008(9) 0.0426(6) Uani 1 1 d . . . . .
H16 H 0.296498 -0.041259 0.299925 0.051 Uiso 1 1 calc R U . . .
C17 C 0.3073(2) -0.00633(14) 0.22892(8) 0.0327(4) Uani 1 1 d . . . . .
H17 H 0.247015 -0.043701 0.214071 0.039 Uiso 1 1 calc R U . . .
C18 C 0.44721(19) -0.02173(11) 0.10655(7) 0.0228(3) Uani 1 1 d . . . . .
C19 C 0.5526(2) -0.05089(12) 0.13384(8) 0.0283(4) Uani 1 1 d . . . . .
H19 H 0.566876 -0.035625 0.168057 0.034 Uiso 1 1 calc R U . . .
C110 C 0.6373(2) -0.10233(14) 0.11124(9) 0.0371(5) Uani 1 1 d . . . . .
H110 H 0.708616 -0.122347 0.130253 0.045 Uiso 1 1 calc R U . . .
C111 C 0.6187(3) -0.12444(15) 0.06173(10) 0.0441(6) Uani 1 1 d . . . . .
H111 H 0.677072 -0.159375 0.046463 0.053 Uiso 1 1 calc R U . . .
C112 C 0.5144(3) -0.09553(18) 0.03427(10) 0.0520(7) Uani 1 1 d . . . . .
H112 H 0.501811 -0.110147 -0.000111 0.062 Uiso 1 1 calc R U . . .
C113 C 0.4284(3) -0.04540(15) 0.05658(9) 0.0402(5) Uani 1 1 d . . . . .
H113 H 0.355667 -0.026973 0.037581 0.048 Uiso 1 1 calc R U . . .
C120 C 0.2574(2) 0.27176(12) 0.10834(9) 0.0340(5) Uani 1 1 d . . . . .
C121 C 0.1234(3) 0.30312(15) 0.11894(14) 0.0565(8) Uani 1 1 d . . . . .
H12A H 0.058787 0.278281 0.095215 0.085 Uiso 1 1 calc R U . . .
H12B H 0.122390 0.359827 0.115545 0.085 Uiso 1 1 calc R U . . .
H12C H 0.103199 0.291374 0.152858 0.085 Uiso 1 1 calc R U . . .
C122 C 0.2867(4) 0.28714(16) 0.05471(11) 0.0546(8) Uani 1 1 d . . . . .
H12D H 0.373556 0.268302 0.048201 0.082 Uiso 1 1 calc R U . . .
H12E H 0.282296 0.343389 0.049745 0.082 Uiso 1 1 calc R U . . .
H12F H 0.223029 0.259583 0.031835 0.082 Uiso 1 1 calc R U . . .
C123 C 0.3538(3) 0.31248(14) 0.14637(10) 0.0424(6) Uani 1 1 d . . . . .
H12G H 0.335942 0.297076 0.179844 0.064 Uiso 1 1 calc R U . . .
H12H H 0.345354 0.369259 0.144655 0.064 Uiso 1 1 calc R U . . .
H12I H 0.441941 0.297171 0.138965 0.064 Uiso 1 1 calc R U . . .
C114 C -0.06541(19) 0.11021(14) 0.14653(8) 0.0297(4) Uani 1 1 d . . . . .
C115 C -0.06219(18) 0.08580(13) 0.08990(7) 0.0257(4) Uani 1 1 d . . . . .
C116 C -0.1505(3) 0.1807(2) 0.15713(12) 0.0580(9) Uani 1 1 d . . . . .
H11A H -0.132529 0.200614 0.191536 0.087 Uiso 1 1 calc R U . . .
H11B H -0.241678 0.165182 0.152276 0.087 Uiso 1 1 calc R U . . .
H11C H -0.131986 0.221769 0.134387 0.087 Uiso 1 1 calc R U . . .
C117 C -0.0982(3) 0.0443(2) 0.17953(10) 0.0534(8) Uani 1 1 d . . . . .
H11D H -0.032181 0.003728 0.177473 0.080 Uiso 1 1 calc R U . . .
H11E H -0.182806 0.021977 0.168380 0.080 Uiso 1 1 calc R U . . .
H11F H -0.100816 0.064838 0.214015 0.080 Uiso 1 1 calc R U . . .
C118 C -0.1773(2) 0.10994(18) 0.05761(9) 0.0414(6) Uani 1 1 d . . . . .
H11G H -0.186856 0.166826 0.060809 0.062 Uiso 1 1 calc R U . . .
H11H H -0.255434 0.084600 0.068174 0.062 Uiso 1 1 calc R U . . .
H11I H -0.164367 0.094102 0.022852 0.062 Uiso 1 1 calc R U . . .
C119 C -0.0360(2) -0.00087(14) 0.08008(9) 0.0375(5) Uani 1 1 d . . . . .
H11J H -0.024818 -0.011316 0.044538 0.056 Uiso 1 1 calc R U . . .
H11K H -0.109091 -0.031687 0.090177 0.056 Uiso 1 1 calc R U . . .
H11L H 0.042867 -0.015344 0.099211 0.056 Uiso 1 1 calc R U . . .
C21 C 0.02442(19) 0.63649(12) 0.11196(8) 0.0263(4) Uani 1 1 d . . . . .
P2 P 0.07083(4) 0.53644(3) 0.13121(2) 0.02101(9) Uani 1 1 d . . . . .
S2 S -0.12554(6) 0.65651(4) 0.09271(3) 0.05235(19) Uani 1 1 d . . . . .
N2 N 0.12796(17) 0.68510(9) 0.11734(7) 0.0256(3) Uani 1 1 d . . . . .
B2 B 0.2600(2) 0.65025(12) 0.11838(8) 0.0223(4) Uani 1 1 d . . . . .
O21 O 0.33345(14) 0.63733(9) 0.16003(5) 0.0281(3) Uani 1 1 d . . . . .
O22 O 0.31781(13) 0.63561(8) 0.07508(5) 0.0245(3) Uani 1 1 d . . . . .
C22 C 0.04190(18) 0.54528(11) 0.19732(7) 0.0232(3) Uani 1 1 d . . . . .
C23 C -0.0404(2) 0.59985(13) 0.21871(9) 0.0358(5) Uani 1 1 d . . . . .
H23 H -0.088333 0.634353 0.198279 0.043 Uiso 1 1 calc R U . . .
C24 C -0.0524(3) 0.60387(16) 0.26977(10) 0.0461(6) Uani 1 1 d . . . . .
H24 H -0.107318 0.641782 0.284212 0.055 Uiso 1 1 calc R U . . .
C25 C 0.0147(3) 0.55342(18) 0.29947(9) 0.0465(7) Uani 1 1 d . . . . .
H25 H 0.005404 0.556373 0.334351 0.056 Uiso 1 1 calc R U . . .
C26 C 0.0951(2) 0.49870(19) 0.27921(9) 0.0464(6) Uani 1 1 d . . . . .
H26 H 0.140571 0.463458 0.299912 0.056 Uiso 1 1 calc R U . . .
C27 C 0.1098(2) 0.49508(15) 0.22820(8) 0.0336(5) Uani 1 1 d . . . . .
H27 H 0.166934 0.457902 0.214294 0.040 Uiso 1 1 calc R U . . .
C28 C -0.06076(19) 0.47499(11) 0.10387(7) 0.0244(4) Uani 1 1 d . . . . .
C29 C -0.1633(2) 0.44777(13) 0.12929(8) 0.0305(4) Uani 1 1 d . . . . .
H29 H -0.171820 0.464196 0.163088 0.037 Uiso 1 1 calc R U . . .
C210 C -0.2537(2) 0.39634(15) 0.10522(10) 0.0390(5) Uani 1 1 d . . . . .
H210 H -0.322967 0.377200 0.122920 0.047 Uiso 1 1 calc R U . . .
C211 C -0.2436(3) 0.37292(15) 0.05587(10) 0.0447(6) Uani 1 1 d . . . . .
H211 H -0.306593 0.338617 0.039540 0.054 Uiso 1 1 calc R U . . .
C212 C -0.1421(3) 0.39946(18) 0.03047(9) 0.0483(6) Uani 1 1 d . . . . .
H212 H -0.135123 0.383655 -0.003518 0.058 Uiso 1 1 calc R U . . .
C213 C -0.0499(2) 0.44919(15) 0.05433(8) 0.0378(5) Uani 1 1 d . . . . .
H213 H 0.021460 0.465928 0.036826 0.045 Uiso 1 1 calc R U . . .
C220 C 0.1203(3) 0.77267(12) 0.11242(9) 0.0372(5) Uani 1 1 d . . . . .
C221 C 0.2545(3) 0.80691(15) 0.12677(14) 0.0588(9) Uani 1 1 d . . . . .
H22A H 0.282386 0.791717 0.160267 0.088 Uiso 1 1 calc R U . . .
H22B H 0.251330 0.864038 0.126205 0.088 Uiso 1 1 calc R U . . .
H22C H 0.315998 0.786939 0.103022 0.088 Uiso 1 1 calc R U . . .
C222 C 0.0824(4) 0.79114(16) 0.05883(11) 0.0588(9) Uani 1 1 d . . . . .
H22D H 0.143531 0.766312 0.036668 0.088 Uiso 1 1 calc R U . . .
H22E H 0.084425 0.847861 0.055548 0.088 Uiso 1 1 calc R U . . .
H22F H -0.004975 0.771127 0.049814 0.088 Uiso 1 1 calc R U . . .
C223 C 0.0282(3) 0.80757(14) 0.14954(11) 0.0476(7) Uani 1 1 d . . . . .
H22G H -0.059673 0.787920 0.140908 0.071 Uiso 1 1 calc R U . . .
H22H H 0.029371 0.864671 0.148422 0.071 Uiso 1 1 calc R U . . .
H22I H 0.055595 0.792526 0.183110 0.071 Uiso 1 1 calc R U . . .
C214 C 0.46187(19) 0.61434(14) 0.14469(8) 0.0309(4) Uani 1 1 d . . . . .
C215 C 0.43873(18) 0.59574(13) 0.08704(8) 0.0286(4) Uani 1 1 d . . . . .
C217 C 0.5504(3) 0.6846(2) 0.15722(12) 0.0597(9) Uani 1 1 d . . . . .
H21A H 0.523744 0.727639 0.136346 0.090 Uiso 1 1 calc R U . . .
H21B H 0.639748 0.670276 0.151048 0.090 Uiso 1 1 calc R U . . .
H21C H 0.544774 0.701131 0.192322 0.090 Uiso 1 1 calc R U . . .
C216 C 0.5065(3) 0.5456(2) 0.17450(11) 0.0549(8) Uani 1 1 d . . . . .
H21D H 0.521038 0.562759 0.209589 0.082 Uiso 1 1 calc R U . . .
H21E H 0.587197 0.525229 0.161931 0.082 Uiso 1 1 calc R U . . .
H21F H 0.440056 0.504474 0.171260 0.082 Uiso 1 1 calc R U . . .
C219 C 0.5410(2) 0.6257(2) 0.05499(10) 0.0493(7) Uani 1 1 d . . . . .
H21G H 0.519029 0.609980 0.020096 0.074 Uiso 1 1 calc R U . . .
H21H H 0.625018 0.603834 0.065289 0.074 Uiso 1 1 calc R U . . .
H21I H 0.545487 0.682902 0.058773 0.074 Uiso 1 1 calc R U . . .
C218 C 0.4117(2) 0.50914(15) 0.07352(10) 0.0425(6) Uani 1 1 d . . . . .
H21J H 0.343778 0.490219 0.093871 0.064 Uiso 1 1 calc R U . . .
H21K H 0.490733 0.479114 0.079785 0.064 Uiso 1 1 calc R U . . .
H21L H 0.383206 0.502660 0.038268 0.064 Uiso 1 1 calc R U . . .
C31 C -0.05339(18) 0.87347(11) 0.34006(7) 0.0231(3) Uani 1 1 d . . . . .
P3 P 0.04879(5) 0.82457(3) 0.38914(2) 0.02155(10) Uani 1 1 d . . . . .
S3 S 0.00187(6) 0.94991(3) 0.31226(2) 0.03764(13) Uani 1 1 d . . . . .
N3 N -0.16799(15) 0.83589(10) 0.33225(6) 0.0212(3) Uani 1 1 d . . . . .
B3 B -0.20885(19) 0.78130(12) 0.36990(7) 0.0193(4) Uani 1 1 d . . . . .
C32 C 0.14900(18) 0.76073(11) 0.35129(7) 0.0229(3) Uani 1 1 d . . . . .
C33 C 0.2003(2) 0.69540(12) 0.37429(8) 0.0277(4) Uani 1 1 d . . . . .
H33 H 0.180448 0.685946 0.407436 0.033 Uiso 1 1 calc R U . . .
C34 C 0.2800(2) 0.64423(13) 0.34909(9) 0.0346(5) Uani 1 1 d . . . . .
H34 H 0.315939 0.600685 0.365335 0.041 Uiso 1 1 calc R U . . .
C35 C 0.3072(2) 0.65628(14) 0.30065(10) 0.0373(5) Uani 1 1 d . . . . .
H35 H 0.361421 0.620974 0.283453 0.045 Uiso 1 1 calc R U . . .
C36 C 0.2556(3) 0.71962(15) 0.27721(10) 0.0403(5) Uani 1 1 d . . . . .
H36 H 0.273867 0.727547 0.243696 0.048 Uiso 1 1 calc R U . . .
C37 C 0.1770(2) 0.77220(13) 0.30212(8) 0.0334(4) Uani 1 1 d . . . . .
H37 H 0.142297 0.815891 0.285654 0.040 Uiso 1 1 calc R U . . .
C38 C 0.16058(19) 0.90193(11) 0.41334(7) 0.0240(4) Uani 1 1 d . . . . .
C39 C 0.1126(2) 0.96089(14) 0.44440(9) 0.0383(5) Uani 1 1 d . . . . .
H39 H 0.022811 0.962114 0.449877 0.046 Uiso 1 1 calc R U . . .
C310 C 0.1943(3) 1.01797(15) 0.46748(10) 0.0475(6) Uani 1 1 d . . . . .
H310 H 0.160114 1.058240 0.488237 0.057 Uiso 1 1 calc R U . . .
C311 C 0.3252(3) 1.01620(15) 0.46027(9) 0.0425(6) Uani 1 1 d . . . . .
H311 H 0.381275 1.054829 0.476339 0.051 Uiso 1 1 calc R U . . .
C312 C 0.3741(2) 0.95831(15) 0.42975(9) 0.0389(5) Uani 1 1 d . . . . .
H312 H 0.464101 0.957158 0.424731 0.047 Uiso 1 1 calc R U . . .
C313 C 0.2923(2) 0.90120(13) 0.40609(8) 0.0300(4) Uani 1 1 d . . . . .
H313 H 0.326924 0.861639 0.384918 0.036 Uiso 1 1 calc R U . . .
C320 C -0.26511(19) 0.85107(13) 0.28963(7) 0.0268(4) Uani 1 1 d . . . . .
C321 C -0.3791(2) 0.79403(19) 0.29201(10) 0.0472(6) Uani 1 1 d . . . . .
H32A H -0.347326 0.740222 0.290293 0.071 Uiso 1 1 calc R U . . .
H32B H -0.441490 0.801549 0.263968 0.071 Uiso 1 1 calc R U . . .
H32C H -0.421194 0.803901 0.323305 0.071 Uiso 1 1 calc R U . . .
C322 C -0.2029(3) 0.83454(16) 0.24045(8) 0.0402(5) Uani 1 1 d . . . . .
H32D H -0.133688 0.872789 0.237009 0.060 Uiso 1 1 calc R U . . .
H32E H -0.268198 0.838400 0.212935 0.060 Uiso 1 1 calc R U . . .
H32F H -0.166635 0.781773 0.239763 0.060 Uiso 1 1 calc R U . . .
C323 C -0.3161(3) 0.93405(16) 0.29444(11) 0.0465(6) Uani 1 1 d . . . . .
H32G H -0.355275 0.942168 0.326490 0.070 Uiso 1 1 calc R U . . .
H32H H -0.381286 0.942166 0.267413 0.070 Uiso 1 1 calc R U . . .
H32I H -0.244633 0.971264 0.292519 0.070 Uiso 1 1 calc R U . . .
O31 O -0.189(3) 0.7118(10) 0.3668(10) 0.0200(11) Uani 0.396(4) 1 d . U P A 1
O32 O -0.2899(16) 0.8044(14) 0.4054(8) 0.0201(11) Uani 0.396(4) 1 d . U P A 1
C314 C -0.261(2) 0.6612(13) 0.4039(10) 0.0221(13) Uani 0.396(4) 1 d . U P A 1
C315 C -0.302(2) 0.7295(9) 0.4349(9) 0.0207(12) Uani 0.396(4) 1 d . U P A 1
C316 C -0.3721(11) 0.6234(6) 0.3750(4) 0.0562(16) Uani 0.396(4) 1 d . U P A 1
H31A H -0.428674 0.663591 0.361214 0.084 Uiso 0.396(4) 1 calc R U P A 1
H31B H -0.420596 0.591509 0.396855 0.084 Uiso 0.396(4) 1 calc R U P A 1
H31C H -0.340489 0.589961 0.347825 0.084 Uiso 0.396(4) 1 calc R U P A 1
C317 C -0.1710(8) 0.6078(5) 0.4289(3) 0.0461(10) Uani 0.396(4) 1 d . U P A 1
H31D H -0.142240 0.568054 0.404689 0.069 Uiso 0.396(4) 1 calc R U P A 1
H31E H -0.214720 0.582299 0.455128 0.069 Uiso 0.396(4) 1 calc R U P A 1
H31F H -0.095944 0.637396 0.443661 0.069 Uiso 0.396(4) 1 calc R U P A 1
C318 C -0.2070(7) 0.7535(5) 0.4842(3) 0.0442(8) Uani 0.396(4) 1 d . U P A 1
H31G H -0.234841 0.803406 0.499196 0.066 Uiso 0.396(4) 1 calc R U P A 1
H31H H -0.117810 0.758462 0.474451 0.066 Uiso 0.396(4) 1 calc R U P A 1
H31I H -0.211658 0.712823 0.508443 0.066 Uiso 0.396(4) 1 calc R U P A 1
C319 C -0.4368(7) 0.7349(4) 0.4534(3) 0.0403(8) Uani 0.396(4) 1 d . U P A 1
H31J H -0.448914 0.694099 0.477038 0.060 Uiso 0.396(4) 1 calc R U P A 1
H31K H -0.500480 0.727705 0.425254 0.060 Uiso 0.396(4) 1 calc R U P A 1
H31L H -0.448238 0.786343 0.470015 0.060 Uiso 0.396(4) 1 calc R U P A 1
O51 O -0.1963(16) 0.6975(5) 0.3645(6) 0.0200(11) Uani 0.604(4) 1 d . U P A 2
O52 O -0.2666(9) 0.8085(9) 0.4117(5) 0.0201(11) Uani 0.604(4) 1 d . U P A 2
C514 C -0.2440(14) 0.6730(7) 0.4097(6) 0.0221(13) Uani 0.604(4) 1 d . U P A 2
C515 C -0.3137(14) 0.7452(5) 0.4377(5) 0.0207(12) Uani 0.604(4) 1 d . U P A 2
C516 C -0.3333(7) 0.6012(4) 0.3942(2) 0.0562(16) Uani 0.604(4) 1 d . U P A 2
H51A H -0.399374 0.616311 0.369026 0.084 Uiso 0.604(4) 1 calc R U P A 2
H51B H -0.375344 0.583680 0.423383 0.084 Uiso 0.604(4) 1 calc R U P A 2
H51C H -0.281379 0.558669 0.380402 0.084 Uiso 0.604(4) 1 calc R U P A 2
C517 C -0.1245(5) 0.6440(3) 0.4399(2) 0.0461(10) Uani 0.604(4) 1 d . U P A 2
H51D H -0.077359 0.606604 0.419189 0.069 Uiso 0.604(4) 1 calc R U P A 2
H51E H -0.152162 0.618338 0.469270 0.069 Uiso 0.604(4) 1 calc R U P A 2
H51F H -0.068045 0.688486 0.450421 0.069 Uiso 0.604(4) 1 calc R U P A 2
C518 C -0.4621(4) 0.7383(3) 0.4276(2) 0.0442(8) Uani 0.604(4) 1 d . U P A 2
H51G H -0.503226 0.785720 0.440757 0.066 Uiso 0.604(4) 1 calc R U P A 2
H51H H -0.494358 0.692845 0.444065 0.066 Uiso 0.604(4) 1 calc R U P A 2
H51I H -0.482705 0.731832 0.391740 0.066 Uiso 0.604(4) 1 calc R U P A 2
C519 C -0.2794(5) 0.7552(3) 0.49024(14) 0.0403(8) Uani 0.604(4) 1 d . U P A 2
H51J H -0.185292 0.760565 0.495476 0.060 Uiso 0.604(4) 1 calc R U P A 2
H51K H -0.308819 0.709621 0.507184 0.060 Uiso 0.604(4) 1 calc R U P A 2
H51L H -0.320721 0.802347 0.503740 0.060 Uiso 0.604(4) 1 calc R U P A 2
C41 C 0.50445(18) 0.37538(11) 0.33830(7) 0.0228(3) Uani 1 1 d . . . . .
P4 P 0.41801(5) 0.32644(3) 0.38774(2) 0.02122(9) Uani 1 1 d . . . . .
S4 S 0.44102(6) 0.45126(3) 0.31040(2) 0.03745(13) Uani 1 1 d . . . . .
B4 B 0.66905(19) 0.28394(12) 0.36785(7) 0.0205(4) Uani 1 1 d . . . . .
N4 N 0.61591(15) 0.33781(10) 0.32998(6) 0.0223(3) Uani 1 1 d . . . . .
C42 C 0.31426(19) 0.40334(11) 0.41194(7) 0.0238(4) Uani 1 1 d . . . . .
C43 C 0.3719(2) 0.46167(13) 0.44385(9) 0.0361(5) Uani 1 1 d . . . . .
H43 H 0.463173 0.462754 0.449900 0.043 Uiso 1 1 calc R U . . .
C44 C 0.2969(3) 0.51818(14) 0.46685(10) 0.0434(6) Uani 1 1 d . . . . .
H44 H 0.337196 0.558098 0.488124 0.052 Uiso 1 1 calc R U . . .
C45 C 0.1642(3) 0.51655(14) 0.45892(9) 0.0407(6) Uani 1 1 d . . . . .
H45 H 0.113054 0.554860 0.475040 0.049 Uiso 1 1 calc R U . . .
C46 C 0.1059(2) 0.45923(14) 0.42755(9) 0.0374(5) Uani 1 1 d . . . . .
H46 H 0.014447 0.458040 0.422179 0.045 Uiso 1 1 calc R U . . .
C47 C 0.1801(2) 0.40317(13) 0.40375(8) 0.0298(4) Uani 1 1 d . . . . .
H47 H 0.139199 0.364432 0.381740 0.036 Uiso 1 1 calc R U . . .
C48 C 0.30602(18) 0.26153(11) 0.35030(7) 0.0229(3) Uani 1 1 d . . . . .
C49 C 0.2625(2) 0.27264(14) 0.30134(8) 0.0341(5) Uani 1 1 d . . . . .
H49 H 0.291883 0.316562 0.284841 0.041 Uiso 1 1 calc R U . . .
C410 C 0.1760(2) 0.21969(15) 0.27643(10) 0.0407(5) Uani 1 1 d . . . . .
H410 H 0.147227 0.227486 0.242947 0.049 Uiso 1 1 calc R U . . .
C411 C 0.1319(2) 0.15606(14) 0.30009(10) 0.0381(5) Uani 1 1 d . . . . .
H411 H 0.072238 0.120420 0.283015 0.046 Uiso 1 1 calc R U . . .
C412 C 0.1743(2) 0.14409(13) 0.34857(9) 0.0351(5) Uani 1 1 d . . . . .
H412 H 0.143591 0.100324 0.364902 0.042 Uiso 1 1 calc R U . . .
C413 C 0.2617(2) 0.19597(12) 0.37346(8) 0.0280(4) Uani 1 1 d . . . . .
H413 H 0.291862 0.186868 0.406606 0.034 Uiso 1 1 calc R U . . .
C420 C 0.6988(2) 0.35209(13) 0.28657(7) 0.0287(4) Uani 1 1 d . . . . .
C421 C 0.8117(3) 0.29532(19) 0.28860(10) 0.0496(7) Uani 1 1 d . . . . .
H42A H 0.862296 0.303954 0.320245 0.074 Uiso 1 1 calc R U . . .
H42B H 0.866873 0.304024 0.261029 0.074 Uiso 1 1 calc R U . . .
H42C H 0.778509 0.241520 0.285820 0.074 Uiso 1 1 calc R U . . .
C422 C 0.6190(3) 0.33466(16) 0.23798(8) 0.0419(6) Uani 1 1 d . . . . .
H42D H 0.584070 0.281347 0.237521 0.063 Uiso 1 1 calc R U . . .
H42E H 0.674085 0.339577 0.209916 0.063 Uiso 1 1 calc R U . . .
H42F H 0.547696 0.371853 0.235254 0.063 Uiso 1 1 calc R U . . .
C423 C 0.7523(3) 0.43530(16) 0.29066(11) 0.0471(6) Uani 1 1 d . . . . .
H42G H 0.681874 0.472129 0.284270 0.071 Uiso 1 1 calc R U . . .
H42H H 0.817572 0.440983 0.266160 0.071 Uiso 1 1 calc R U . . .
H42I H 0.791854 0.446301 0.324171 0.071 Uiso 1 1 calc R U . . .
O41 O 0.6613(4) 0.2077(3) 0.36141(16) 0.0212(4) Uiso 0.472(4) 1 d . . P B 3
O42 O 0.7583(4) 0.3093(2) 0.40351(15) 0.0221(4) Uiso 0.472(4) 1 d . . P B 3
C414 C 0.7143(5) 0.1723(3) 0.4106(2) 0.0231(5) Uiso 0.472(4) 1 d . . P B 3
C415 C 0.8001(6) 0.2463(4) 0.4322(2) 0.0222(5) Uiso 0.472(4) 1 d . . P B 3
C416 C 0.7945(9) 0.1027(5) 0.3958(3) 0.0552(17) Uani 0.472(4) 1 d . U P B 3
H41A H 0.843504 0.084558 0.425146 0.083 Uiso 0.472(4) 1 calc R U P B 3
H41B H 0.854631 0.117813 0.371093 0.083 Uiso 0.472(4) 1 calc R U P B 3
H41C H 0.737594 0.060628 0.381436 0.083 Uiso 0.472(4) 1 calc R U P B 3
C417 C 0.6028(7) 0.1498(5) 0.4394(3) 0.0503(14) Uani 0.472(4) 1 d . U P B 3
H41D H 0.545052 0.114605 0.418671 0.075 Uiso 0.472(4) 1 calc R U P B 3
H41E H 0.555525 0.196795 0.449526 0.075 Uiso 0.472(4) 1 calc R U P B 3
H41F H 0.634452 0.123174 0.469075 0.075 Uiso 0.472(4) 1 calc R U P B 3
C418 C 0.9284(7) 0.2400(5) 0.4480(3) 0.0467(12) Uani 0.472(4) 1 d . U P B 3
H41G H 0.981678 0.237011 0.419144 0.070 Uiso 0.472(4) 1 calc R U P B 3
H41H H 0.940497 0.192696 0.466763 0.070 Uiso 0.472(4) 1 calc R U P B 3
H41I H 0.954384 0.285923 0.469476 0.070 Uiso 0.472(4) 1 calc R U P B 3
C419 C 0.7089(7) 0.2596(4) 0.4821(2) 0.0424(10) Uani 0.472(4) 1 d . U P B 3
H41J H 0.723935 0.216609 0.504454 0.064 Uiso 0.472(4) 1 calc R U P B 3
H41K H 0.617319 0.260473 0.470910 0.064 Uiso 0.472(4) 1 calc R U P B 3
H41L H 0.732866 0.309264 0.499880 0.064 Uiso 0.472(4) 1 calc R U P B 3
O61 O 0.6439(4) 0.2036(2) 0.36660(14) 0.0212(4) Uiso 0.528(4) 1 d . . P B 4
O62 O 0.7390(3) 0.3122(2) 0.40962(14) 0.0221(4) Uiso 0.528(4) 1 d . . P B 4
C614 C 0.7295(5) 0.1720(3) 0.40235(18) 0.0231(5) Uiso 0.528(4) 1 d . . P B 4
C615 C 0.7821(5) 0.2416(3) 0.4367(2) 0.0222(5) Uiso 0.528(4) 1 d . . P B 4
C616 C 0.8295(8) 0.1222(5) 0.3762(3) 0.0552(17) Uani 0.528(4) 1 d . U P B 4
H61A H 0.785437 0.079947 0.355927 0.083 Uiso 0.528(4) 1 calc R U P B 4
H61B H 0.889323 0.099896 0.401052 0.083 Uiso 0.528(4) 1 calc R U P B 4
H61C H 0.877782 0.154923 0.354718 0.083 Uiso 0.528(4) 1 calc R U P B 4
C617 C 0.6446(6) 0.1170(4) 0.4307(3) 0.0503(14) Uani 0.528(4) 1 d . U P B 4
H61D H 0.572365 0.146509 0.444006 0.075 Uiso 0.528(4) 1 calc R U P B 4
H61E H 0.696730 0.095351 0.458208 0.075 Uiso 0.528(4) 1 calc R U P B 4
H61F H 0.610946 0.074388 0.408029 0.075 Uiso 0.528(4) 1 calc R U P B 4
C618 C 0.9411(6) 0.2433(4) 0.4232(3) 0.0467(12) Uani 0.528(4) 1 d . U P B 4
H61G H 0.980354 0.293225 0.435393 0.070 Uiso 0.528(4) 1 calc R U P B 4
H61H H 0.947679 0.237128 0.387071 0.070 Uiso 0.528(4) 1 calc R U P B 4
H61I H 0.986572 0.200361 0.439247 0.070 Uiso 0.528(4) 1 calc R U P B 4
C619 C 0.7811(6) 0.2592(3) 0.48889(18) 0.0424(10) Uani 0.528(4) 1 d . U P B 4
H61J H 0.835605 0.305281 0.497782 0.064 Uiso 0.528(4) 1 calc R U P B 4
H61K H 0.814744 0.214562 0.506893 0.064 Uiso 0.528(4) 1 calc R U P B 4
H61L H 0.692401 0.269858 0.497884 0.064 Uiso 0.528(4) 1 calc R U P B 4


_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
C11 N1 1.342(2) . ?
C11 S1 1.6567(19) . ?
C11 P1 1.8779(19) . ?
P1 C18 1.817(2) . ?
P1 C12 1.8263(19) . ?
N1 B1 1.493(3) . ?
N1 C120 1.513(2) . ?
B1 O11 1.358(3) . ?
B1 O12 1.360(2) . ?
O11 C114 1.466(2) . ?
O12 C115 1.473(2) . ?
C12 C13 1.388(3) . ?
C12 C17 1.395(3) . ?
C13 C14 1.390(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.390(3) . ?
C18 C113 1.391(3) . ?
C19 C110 1.391(3) . ?
C19 H19 0.9500 . ?
C110 C111 1.373(4) . ?
C110 H110 0.9500 . ?
C111 C112 1.381(4) . ?
C111 H111 0.9500 . ?
C112 C113 1.384(4) . ?
C112 H112 0.9500 . ?
C113 H113 0.9500 . ?
C120 C121 1.528(4) . ?
C120 C122 1.530(4) . ?
C120 C123 1.531(3) . ?
C121 H12A 0.9800 . ?
C121 H12B 0.9800 . ?
C121 H12C 0.9800 . ?
C122 H12D 0.9800 . ?
C122 H12E 0.9800 . ?
C122 H12F 0.9800 . ?
C123 H12G 0.9800 . ?
C123 H12H 0.9800 . ?
C123 H12I 0.9800 . ?
C114 C117 1.519(4) . ?
C114 C116 1.525(3) . ?
C114 C115 1.566(3) . ?
C115 C118 1.507(3) . ?
C115 C119 1.524(3) . ?
C116 H11A 0.9800 . ?
C116 H11B 0.9800 . ?
C116 H11C 0.9800 . ?
C117 H11D 0.9800 . ?
C117 H11E 0.9800 . ?
C117 H11F 0.9800 . ?
C118 H11G 0.9800 . ?
C118 H11H 0.9800 . ?
C118 H11I 0.9800 . ?
C119 H11J 0.9800 . ?
C119 H11K 0.9800 . ?
C119 H11L 0.9800 . ?
C21 N2 1.352(3) . ?
C21 S2 1.652(2) . ?
C21 P2 1.871(2) . ?
P2 C28 1.818(2) . ?
P2 C22 1.824(2) . ?
N2 B2 1.495(3) . ?
N2 C220 1.514(2) . ?
B2 O21 1.348(3) . ?
B2 O22 1.356(2) . ?
O21 C214 1.466(2) . ?
O22 C215 1.457(2) . ?
C22 C27 1.391(3) . ?
C22 C23 1.395(3) . ?
C23 C24 1.388(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.371(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.372(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.391(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.388(3) . ?
C28 C213 1.398(3) . ?
C29 C210 1.393(3) . ?
C29 H29 0.9500 . ?
C210 C211 1.381(4) . ?
C210 H210 0.9500 . ?
C211 C212 1.375(4) . ?
C211 H211 0.9500 . ?
C212 C213 1.386(4) . ?
C212 H212 0.9500 . ?
C213 H213 0.9500 . ?
C220 C222 1.524(4) . ?
C220 C223 1.526(3) . ?
C220 C221 1.528(4) . ?
C221 H22A 0.9800 . ?
C221 H22B 0.9800 . ?
C221 H22C 0.9800 . ?
C222 H22D 0.9800 . ?
C222 H22E 0.9800 . ?
C222 H22F 0.9800 . ?
C223 H22G 0.9800 . ?
C223 H22H 0.9800 . ?
C223 H22I 0.9800 . ?
C214 C216 1.516(4) . ?
C214 C217 1.523(3) . ?
C214 C215 1.576(3) . ?
C215 C219 1.509(3) . ?
C215 C218 1.531(3) . ?
C217 H21A 0.9800 . ?
C217 H21B 0.9800 . ?
C217 H21C 0.9800 . ?
C216 H21D 0.9800 . ?
C216 H21E 0.9800 . ?
C216 H21F 0.9800 . ?
C219 H21G 0.9800 . ?
C219 H21H 0.9800 . ?
C219 H21I 0.9800 . ?
C218 H21J 0.9800 . ?
C218 H21K 0.9800 . ?
C218 H21L 0.9800 . ?
C31 N3 1.349(2) . ?
C31 S3 1.6555(19) . ?
C31 P3 1.8782(19) . ?
P3 C38 1.827(2) . ?
P3 C32 1.828(2) . ?
N3 B3 1.490(2) . ?
N3 C320 1.516(2) . ?
B3 O31 1.207(19) . ?
B3 O32 1.35(2) . ?
B3 O52 1.368(14) . ?
B3 O51 1.443(10) . ?
C32 C37 1.396(3) . ?
C32 C33 1.398(3) . ?
C33 C34 1.388(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.377(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.377(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.392(3) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 C313 1.390(3) . ?
C38 C39 1.393(3) . ?
C39 C310 1.390(3) . ?
C39 H39 0.9500 . ?
C310 C311 1.381(4) . ?
C310 H310 0.9500 . ?
C311 C312 1.375(4) . ?
C311 H311 0.9500 . ?
C312 C313 1.397(3) . ?
C312 H312 0.9500 . ?
C313 H313 0.9500 . ?
C320 C323 1.521(3) . ?
C320 C322 1.523(3) . ?
C320 C321 1.535(3) . ?
C321 H32A 0.9800 . ?
C321 H32B 0.9800 . ?
C321 H32C 0.9800 . ?
C322 H32D 0.9800 . ?
C322 H32E 0.9800 . ?
C322 H32F 0.9800 . ?
C323 H32G 0.9800 . ?
C323 H32H 0.9800 . ?
C323 H32I 0.9800 . ?
O31 C314 1.57(4) . ?
O32 C315 1.55(3) . ?
C314 C317 1.47(3) . ?
C314 C316 1.481(19) . ?
C314 C315 1.48(3) . ?
C315 C319 1.51(2) . ?
C315 C318 1.64(3) . ?
C316 H31A 0.9800 . ?
C316 H31B 0.9800 . ?
C316 H31C 0.9800 . ?
C317 H31D 0.9800 . ?
C317 H31E 0.9800 . ?
C317 H31F 0.9800 . ?
C318 H31G 0.9800 . ?
C318 H31H 0.9800 . ?
C318 H31I 0.9800 . ?
C319 H31J 0.9800 . ?
C319 H31K 0.9800 . ?
C319 H31L 0.9800 . ?
O51 C514 1.42(2) . ?
O52 C515 1.42(2) . ?
C514 C517 1.539(17) . ?
C514 C516 1.561(9) . ?
C514 C515 1.612(17) . ?
C515 C519 1.443(16) . ?
C515 C518 1.549(16) . ?
C516 H51A 0.9800 . ?
C516 H51B 0.9800 . ?
C516 H51C 0.9800 . ?
C517 H51D 0.9800 . ?
C517 H51E 0.9800 . ?
C517 H51F 0.9800 . ?
C518 H51G 0.9800 . ?
C518 H51H 0.9800 . ?
C518 H51I 0.9800 . ?
C519 H51J 0.9800 . ?
C519 H51K 0.9800 . ?
C519 H51L 0.9800 . ?
C41 N4 1.349(2) . ?
C41 S4 1.6531(19) . ?
C41 P4 1.8762(19) . ?
P4 C42 1.824(2) . ?
P4 C48 1.829(2) . ?
B4 O41 1.310(5) . ?
B4 O42 1.350(5) . ?
B4 O62 1.370(4) . ?
B4 O61 1.398(4) . ?
B4 N4 1.493(3) . ?
N4 C420 1.519(2) . ?
C42 C47 1.394(3) . ?
C42 C43 1.396(3) . ?
C43 C44 1.389(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.379(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.378(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.389(3) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 C49 1.393(3) . ?
C48 C413 1.399(3) . ?
C49 C410 1.393(3) . ?
C49 H49 0.9500 . ?
C410 C411 1.378(4) . ?
C410 H410 0.9500 . ?
C411 C412 1.380(4) . ?
C411 H411 0.9500 . ?
C412 C413 1.388(3) . ?
C412 H412 0.9500 . ?
C413 H413 0.9500 . ?
C420 C423 1.523(3) . ?
C420 C422 1.524(3) . ?
C420 C421 1.525(3) . ?
C421 H42A 0.9800 . ?
C421 H42B 0.9800 . ?
C421 H42C 0.9800 . ?
C422 H42D 0.9800 . ?
C422 H42E 0.9800 . ?
C422 H42F 0.9800 . ?
C423 H42G 0.9800 . ?
C423 H42H 0.9800 . ?
C423 H42I 0.9800 . ?
O41 C414 1.559(7) . ?
O42 C415 1.414(8) . ?
C414 C417 1.488(9) . ?
C414 C416 1.507(9) . ?
C414 C415 1.610(9) . ?
C415 C418 1.379(9) . ?
C415 C419 1.695(9) . ?
C416 H41A 0.9800 . ?
C416 H41B 0.9800 . ?
C416 H41C 0.9800 . ?
C417 H41D 0.9800 . ?
C417 H41E 0.9800 . ?
C417 H41F 0.9800 . ?
C418 H41G 0.9800 . ?
C418 H41H 0.9800 . ?
C418 H41I 0.9800 . ?
C419 H41J 0.9800 . ?
C419 H41K 0.9800 . ?
C419 H41L 0.9800 . ?
O61 C614 1.401(7) . ?
O62 C615 1.498(7) . ?
C614 C616 1.528(8) . ?
C614 C617 1.544(8) . ?
C614 C615 1.551(8) . ?
C615 C619 1.426(7) . ?
C615 C618 1.708(8) . ?
C616 H61A 0.9800 . ?
C616 H61B 0.9800 . ?
C616 H61C 0.9800 . ?
C617 H61D 0.9800 . ?
C617 H61E 0.9800 . ?
C617 H61F 0.9800 . ?
C618 H61G 0.9800 . ?
C618 H61H 0.9800 . ?
C618 H61I 0.9800 . ?
C619 H61J 0.9800 . ?
C619 H61K 0.9800 . ?
C619 H61L 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
N1 C11 S1 128.42(15) . . ?
N1 C11 P1 110.27(13) . . ?
S1 C11 P1 121.30(11) . . ?
C18 P1 C12 104.41(8) . . ?
C18 P1 C11 103.67(9) . . ?
C12 P1 C11 100.68(8) . . ?
C11 N1 B1 119.06(16) . . ?
C11 N1 C120 124.08(17) . . ?
B1 N1 C120 116.48(16) . . ?
O11 B1 O12 115.10(17) . . ?
O11 B1 N1 123.63(17) . . ?
O12 B1 N1 121.05(18) . . ?
B1 O11 C114 107.31(15) . . ?
B1 O12 C115 106.93(15) . . ?
C13 C12 C17 118.62(19) . . ?
C13 C12 P1 124.88(16) . . ?
C17 C12 P1 116.50(15) . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 119.8(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C12 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C19 C18 C113 118.61(19) . . ?
C19 C18 P1 124.57(15) . . ?
C113 C18 P1 116.52(16) . . ?
C18 C19 C110 120.3(2) . . ?
C18 C19 H19 119.9 . . ?
C110 C19 H19 119.9 . . ?
C111 C110 C19 120.6(2) . . ?
C111 C110 H110 119.7 . . ?
C19 C110 H110 119.7 . . ?
C110 C111 C112 119.5(2) . . ?
C110 C111 H111 120.2 . . ?
C112 C111 H111 120.2 . . ?
C111 C112 C113 120.3(2) . . ?
C111 C112 H112 119.8 . . ?
C113 C112 H112 119.8 . . ?
C112 C113 C18 120.6(2) . . ?
C112 C113 H113 119.7 . . ?
C18 C113 H113 119.7 . . ?
N1 C120 C121 107.84(19) . . ?
N1 C120 C122 109.54(19) . . ?
C121 C120 C122 109.5(2) . . ?
N1 C120 C123 110.23(18) . . ?
C121 C120 C123 107.1(2) . . ?
C122 C120 C123 112.5(2) . . ?
C120 C121 H12A 109.5 . . ?
C120 C121 H12B 109.5 . . ?
H12A C121 H12B 109.5 . . ?
C120 C121 H12C 109.5 . . ?
H12A C121 H12C 109.5 . . ?
H12B C121 H12C 109.5 . . ?
C120 C122 H12D 109.5 . . ?
C120 C122 H12E 109.5 . . ?
H12D C122 H12E 109.5 . . ?
C120 C122 H12F 109.5 . . ?
H12D C122 H12F 109.5 . . ?
H12E C122 H12F 109.5 . . ?
C120 C123 H12G 109.5 . . ?
C120 C123 H12H 109.5 . . ?
H12G C123 H12H 109.5 . . ?
C120 C123 H12I 109.5 . . ?
H12G C123 H12I 109.5 . . ?
H12H C123 H12I 109.5 . . ?
O11 C114 C117 108.21(18) . . ?
O11 C114 C116 105.91(19) . . ?
C117 C114 C116 110.1(2) . . ?
O11 C114 C115 103.49(15) . . ?
C117 C114 C115 114.7(2) . . ?
C116 C114 C115 113.6(2) . . ?
O12 C115 C118 108.79(18) . . ?
O12 C115 C119 105.38(16) . . ?
C118 C115 C119 109.81(19) . . ?
O12 C115 C114 103.00(15) . . ?
C118 C115 C114 115.72(18) . . ?
C119 C115 C114 113.32(18) . . ?
C114 C116 H11A 109.5 . . ?
C114 C116 H11B 109.5 . . ?
H11A C116 H11B 109.5 . . ?
C114 C116 H11C 109.5 . . ?
H11A C116 H11C 109.5 . . ?
H11B C116 H11C 109.5 . . ?
C114 C117 H11D 109.5 . . ?
C114 C117 H11E 109.5 . . ?
H11D C117 H11E 109.5 . . ?
C114 C117 H11F 109.5 . . ?
H11D C117 H11F 109.5 . . ?
H11E C117 H11F 109.5 . . ?
C115 C118 H11G 109.5 . . ?
C115 C118 H11H 109.5 . . ?
H11G C118 H11H 109.5 . . ?
C115 C118 H11I 109.5 . . ?
H11G C118 H11I 109.5 . . ?
H11H C118 H11I 109.5 . . ?
C115 C119 H11J 109.5 . . ?
C115 C119 H11K 109.5 . . ?
H11J C119 H11K 109.5 . . ?
C115 C119 H11L 109.5 . . ?
H11J C119 H11L 109.5 . . ?
H11K C119 H11L 109.5 . . ?
N2 C21 S2 128.43(15) . . ?
N2 C21 P2 110.21(14) . . ?
S2 C21 P2 121.35(12) . . ?
C28 P2 C22 104.72(9) . . ?
C28 P2 C21 103.31(9) . . ?
C22 P2 C21 100.49(9) . . ?
C21 N2 B2 118.44(16) . . ?
C21 N2 C220 123.88(18) . . ?
B2 N2 C220 116.59(17) . . ?
O21 B2 O22 115.47(18) . . ?
O21 B2 N2 124.82(17) . . ?
O22 B2 N2 119.49(18) . . ?
B2 O21 C214 107.25(15) . . ?
B2 O22 C215 107.28(16) . . ?
C27 C22 C23 118.5(2) . . ?
C27 C22 P2 116.98(16) . . ?
C23 C22 P2 124.49(16) . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 120.3(2) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.5(2) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C27 119.7(3) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C26 C27 C22 120.8(2) . . ?
C26 C27 H27 119.6 . . ?
C22 C27 H27 119.6 . . ?
C29 C28 C213 118.8(2) . . ?
C29 C28 P2 125.13(16) . . ?
C213 C28 P2 115.91(16) . . ?
C28 C29 C210 120.0(2) . . ?
C28 C29 H29 120.0 . . ?
C210 C29 H29 120.0 . . ?
C211 C210 C29 120.6(2) . . ?
C211 C210 H210 119.7 . . ?
C29 C210 H210 119.7 . . ?
C212 C211 C210 119.7(2) . . ?
C212 C211 H211 120.1 . . ?
C210 C211 H211 120.1 . . ?
C211 C212 C213 120.2(2) . . ?
C211 C212 H212 119.9 . . ?
C213 C212 H212 119.9 . . ?
C212 C213 C28 120.7(2) . . ?
C212 C213 H213 119.7 . . ?
C28 C213 H213 119.7 . . ?
N2 C220 C222 110.2(2) . . ?
N2 C220 C223 109.61(17) . . ?
C222 C220 C223 113.1(2) . . ?
N2 C220 C221 107.5(2) . . ?
C222 C220 C221 109.1(2) . . ?
C223 C220 C221 107.2(2) . . ?
C220 C221 H22A 109.5 . . ?
C220 C221 H22B 109.5 . . ?
H22A C221 H22B 109.5 . . ?
C220 C221 H22C 109.5 . . ?
H22A C221 H22C 109.5 . . ?
H22B C221 H22C 109.5 . . ?
C220 C222 H22D 109.5 . . ?
C220 C222 H22E 109.5 . . ?
H22D C222 H22E 109.5 . . ?
C220 C222 H22F 109.5 . . ?
H22D C222 H22F 109.5 . . ?
H22E C222 H22F 109.5 . . ?
C220 C223 H22G 109.5 . . ?
C220 C223 H22H 109.5 . . ?
H22G C223 H22H 109.5 . . ?
C220 C223 H22I 109.5 . . ?
H22G C223 H22I 109.5 . . ?
H22H C223 H22I 109.5 . . ?
O21 C214 C216 108.23(19) . . ?
O21 C214 C217 106.31(19) . . ?
C216 C214 C217 110.2(2) . . ?
O21 C214 C215 103.25(15) . . ?
C216 C214 C215 115.0(2) . . ?
C217 C214 C215 113.1(2) . . ?
O22 C215 C219 108.7(2) . . ?
O22 C215 C218 105.48(16) . . ?
C219 C215 C218 109.7(2) . . ?
O22 C215 C214 102.89(15) . . ?
C219 C215 C214 115.83(18) . . ?
C218 C215 C214 113.4(2) . . ?
C214 C217 H21A 109.5 . . ?
C214 C217 H21B 109.5 . . ?
H21A C217 H21B 109.5 . . ?
C214 C217 H21C 109.5 . . ?
H21A C217 H21C 109.5 . . ?
H21B C217 H21C 109.5 . . ?
C214 C216 H21D 109.5 . . ?
C214 C216 H21E 109.5 . . ?
H21D C216 H21E 109.5 . . ?
C214 C216 H21F 109.5 . . ?
H21D C216 H21F 109.5 . . ?
H21E C216 H21F 109.5 . . ?
C215 C219 H21G 109.5 . . ?
C215 C219 H21H 109.5 . . ?
H21G C219 H21H 109.5 . . ?
C215 C219 H21I 109.5 . . ?
H21G C219 H21I 109.5 . . ?
H21H C219 H21I 109.5 . . ?
C215 C218 H21J 109.5 . . ?
C215 C218 H21K 109.5 . . ?
H21J C218 H21K 109.5 . . ?
C215 C218 H21L 109.5 . . ?
H21J C218 H21L 109.5 . . ?
H21K C218 H21L 109.5 . . ?
N3 C31 S3 129.15(15) . . ?
N3 C31 P3 109.89(13) . . ?
S3 C31 P3 120.95(11) . . ?
C38 P3 C32 103.58(9) . . ?
C38 P3 C31 103.33(9) . . ?
C32 P3 C31 101.52(9) . . ?
C31 N3 B3 118.86(15) . . ?
C31 N3 C320 124.00(16) . . ?
B3 N3 C320 116.89(15) . . ?
O31 B3 O32 114.7(16) . . ?
O52 B3 O51 115.4(9) . . ?
O31 B3 N3 123.1(13) . . ?
O32 B3 N3 121.4(10) . . ?
O52 B3 N3 121.0(6) . . ?
O51 B3 N3 123.6(7) . . ?
C37 C32 C33 118.59(19) . . ?
C37 C32 P3 125.34(16) . . ?
C33 C32 P3 116.07(15) . . ?
C34 C33 C32 120.5(2) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C35 C34 C33 120.3(2) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C36 C35 C34 119.8(2) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C35 C36 C37 120.7(2) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 H36 119.7 . . ?
C36 C37 C32 120.0(2) . . ?
C36 C37 H37 120.0 . . ?
C32 C37 H37 120.0 . . ?
C313 C38 C39 118.50(19) . . ?
C313 C38 P3 123.52(16) . . ?
C39 C38 P3 117.71(16) . . ?
C310 C39 C38 120.8(2) . . ?
C310 C39 H39 119.6 . . ?
C38 C39 H39 119.6 . . ?
C311 C310 C39 120.1(2) . . ?
C311 C310 H310 120.0 . . ?
C39 C310 H310 120.0 . . ?
C312 C311 C310 119.8(2) . . ?
C312 C311 H311 120.1 . . ?
C310 C311 H311 120.1 . . ?
C311 C312 C313 120.4(2) . . ?
C311 C312 H312 119.8 . . ?
C313 C312 H312 119.8 . . ?
C38 C313 C312 120.4(2) . . ?
C38 C313 H313 119.8 . . ?
C312 C313 H313 119.8 . . ?
N3 C320 C323 110.55(17) . . ?
N3 C320 C322 109.38(17) . . ?
C323 C320 C322 112.2(2) . . ?
N3 C320 C321 108.20(17) . . ?
C323 C320 C321 108.4(2) . . ?
C322 C320 C321 108.0(2) . . ?
C320 C321 H32A 109.5 . . ?
C320 C321 H32B 109.5 . . ?
H32A C321 H32B 109.5 . . ?
C320 C321 H32C 109.5 . . ?
H32A C321 H32C 109.5 . . ?
H32B C321 H32C 109.5 . . ?
C320 C322 H32D 109.5 . . ?
C320 C322 H32E 109.5 . . ?
H32D C322 H32E 109.5 . . ?
C320 C322 H32F 109.5 . . ?
H32D C322 H32F 109.5 . . ?
H32E C322 H32F 109.5 . . ?
C320 C323 H32G 109.5 . . ?
C320 C323 H32H 109.5 . . ?
H32G C323 H32H 109.5 . . ?
C320 C323 H32I 109.5 . . ?
H32G C323 H32I 109.5 . . ?
H32H C323 H32I 109.5 . . ?
B3 O31 C314 116(2) . . ?
B3 O32 C315 102.3(16) . . ?
C317 C314 C316 115.5(14) . . ?
C317 C314 C315 115.5(18) . . ?
C316 C314 C315 111(2) . . ?
C317 C314 O31 111.0(19) . . ?
C316 C314 O31 106.6(19) . . ?
C315 C314 O31 94.4(17) . . ?
C314 C315 C319 121.7(18) . . ?
C314 C315 O32 109(2) . . ?
C319 C315 O32 103.4(13) . . ?
C314 C315 C318 115.8(17) . . ?
C319 C315 C318 104.1(13) . . ?
O32 C315 C318 100.0(14) . . ?
C314 C316 H31A 109.5 . . ?
C314 C316 H31B 109.5 . . ?
H31A C316 H31B 109.5 . . ?
C314 C316 H31C 109.5 . . ?
H31A C316 H31C 109.5 . . ?
H31B C316 H31C 109.5 . . ?
C314 C317 H31D 109.5 . . ?
C314 C317 H31E 109.5 . . ?
H31D C317 H31E 109.5 . . ?
C314 C317 H31F 109.5 . . ?
H31D C317 H31F 109.5 . . ?
H31E C317 H31F 109.5 . . ?
C315 C318 H31G 109.5 . . ?
C315 C318 H31H 109.5 . . ?
H31G C318 H31H 109.5 . . ?
C315 C318 H31I 109.5 . . ?
H31G C318 H31I 109.5 . . ?
H31H C318 H31I 109.5 . . ?
C315 C319 H31J 109.5 . . ?
C315 C319 H31K 109.5 . . ?
H31J C319 H31K 109.5 . . ?
C315 C319 H31L 109.5 . . ?
H31J C319 H31L 109.5 . . ?
H31K C319 H31L 109.5 . . ?
C514 O51 B3 102.0(10) . . ?
B3 O52 C515 110.3(10) . . ?
O51 C514 C517 105.1(12) . . ?
O51 C514 C516 105.0(8) . . ?
C517 C514 C516 108.4(10) . . ?
O51 C514 C515 109.7(12) . . ?
C517 C514 C515 112.6(9) . . ?
C516 C514 C515 115.3(11) . . ?
O52 C515 C519 110.9(10) . . ?
O52 C515 C518 109.2(9) . . ?
C519 C515 C518 111.2(9) . . ?
O52 C515 C514 100.4(11) . . ?
C519 C515 C514 114.8(10) . . ?
C518 C515 C514 109.8(9) . . ?
C514 C516 H51A 109.5 . . ?
C514 C516 H51B 109.5 . . ?
H51A C516 H51B 109.5 . . ?
C514 C516 H51C 109.5 . . ?
H51A C516 H51C 109.5 . . ?
H51B C516 H51C 109.5 . . ?
C514 C517 H51D 109.5 . . ?
C514 C517 H51E 109.5 . . ?
H51D C517 H51E 109.5 . . ?
C514 C517 H51F 109.5 . . ?
H51D C517 H51F 109.5 . . ?
H51E C517 H51F 109.5 . . ?
C515 C518 H51G 109.5 . . ?
C515 C518 H51H 109.5 . . ?
H51G C518 H51H 109.5 . . ?
C515 C518 H51I 109.5 . . ?
H51G C518 H51I 109.5 . . ?
H51H C518 H51I 109.5 . . ?
C515 C519 H51J 109.5 . . ?
C515 C519 H51K 109.5 . . ?
H51J C519 H51K 109.5 . . ?
C515 C519 H51L 109.5 . . ?
H51J C519 H51L 109.5 . . ?
H51K C519 H51L 109.5 . . ?
N4 C41 S4 128.99(15) . . ?
N4 C41 P4 109.86(13) . . ?
S4 C41 P4 121.12(11) . . ?
C42 P4 C48 103.77(9) . . ?
C42 P4 C41 103.31(9) . . ?
C48 P4 C41 101.48(9) . . ?
O41 B4 O42 114.1(3) . . ?
O62 B4 O61 114.4(3) . . ?
O41 B4 N4 122.6(3) . . ?
O42 B4 N4 120.8(2) . . ?
O62 B4 N4 121.0(2) . . ?
O61 B4 N4 124.3(2) . . ?
C41 N4 B4 118.72(15) . . ?
C41 N4 C420 124.23(16) . . ?
B4 N4 C420 116.80(15) . . ?
C47 C42 C43 118.51(19) . . ?
C47 C42 P4 123.59(16) . . ?
C43 C42 P4 117.66(16) . . ?
C44 C43 C42 120.5(2) . . ?
C44 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C45 C44 C43 120.3(2) . . ?
C45 C44 H44 119.9 . . ?
C43 C44 H44 119.9 . . ?
C46 C45 C44 119.9(2) . . ?
C46 C45 H45 120.1 . . ?
C44 C45 H45 120.1 . . ?
C45 C46 C47 120.4(2) . . ?
C45 C46 H46 119.8 . . ?
C47 C46 H46 119.8 . . ?
C46 C47 C42 120.5(2) . . ?
C46 C47 H47 119.8 . . ?
C42 C47 H47 119.8 . . ?
C49 C48 C413 118.47(19) . . ?
C49 C48 P4 125.18(16) . . ?
C413 C48 P4 116.35(15) . . ?
C48 C49 C410 120.4(2) . . ?
C48 C49 H49 119.8 . . ?
C410 C49 H49 119.8 . . ?
C411 C410 C49 120.4(2) . . ?
C411 C410 H410 119.8 . . ?
C49 C410 H410 119.8 . . ?
C410 C411 C412 120.0(2) . . ?
C410 C411 H411 120.0 . . ?
C412 C411 H411 120.0 . . ?
C411 C412 C413 120.0(2) . . ?
C411 C412 H412 120.0 . . ?
C413 C412 H412 120.0 . . ?
C412 C413 C48 120.8(2) . . ?
C412 C413 H413 119.6 . . ?
C48 C413 H413 119.6 . . ?
N4 C420 C423 110.21(18) . . ?
N4 C420 C422 109.20(17) . . ?
C423 C420 C422 112.3(2) . . ?
N4 C420 C421 108.26(17) . . ?
C423 C420 C421 108.7(2) . . ?
C422 C420 C421 108.0(2) . . ?
C420 C421 H42A 109.5 . . ?
C420 C421 H42B 109.5 . . ?
H42A C421 H42B 109.5 . . ?
C420 C421 H42C 109.5 . . ?
H42A C421 H42C 109.5 . . ?
H42B C421 H42C 109.5 . . ?
C420 C422 H42D 109.5 . . ?
C420 C422 H42E 109.5 . . ?
H42D C422 H42E 109.5 . . ?
C420 C422 H42F 109.5 . . ?
H42D C422 H42F 109.5 . . ?
H42E C422 H42F 109.5 . . ?
C420 C423 H42G 109.5 . . ?
C420 C423 H42H 109.5 . . ?
H42G C423 H42H 109.5 . . ?
C420 C423 H42I 109.5 . . ?
H42G C423 H42I 109.5 . . ?
H42H C423 H42I 109.5 . . ?
B4 O41 C414 107.4(4) . . ?
B4 O42 C415 109.9(4) . . ?
C417 C414 C416 112.1(6) . . ?
C417 C414 O41 108.6(5) . . ?
C416 C414 O41 106.5(5) . . ?
C417 C414 C415 117.1(5) . . ?
C416 C414 C415 113.1(5) . . ?
O41 C414 C415 97.8(4) . . ?
C418 C415 O42 120.3(5) . . ?
C418 C415 C414 122.6(6) . . ?
O42 C415 C414 105.3(5) . . ?
C418 C415 C419 109.7(5) . . ?
O42 C415 C419 100.9(4) . . ?
C414 C415 C419 92.3(4) . . ?
C414 C416 H41A 109.5 . . ?
C414 C416 H41B 109.5 . . ?
H41A C416 H41B 109.5 . . ?
C414 C416 H41C 109.5 . . ?
H41A C416 H41C 109.5 . . ?
H41B C416 H41C 109.5 . . ?
C414 C417 H41D 109.5 . . ?
C414 C417 H41E 109.5 . . ?
H41D C417 H41E 109.5 . . ?
C414 C417 H41F 109.5 . . ?
H41D C417 H41F 109.5 . . ?
H41E C417 H41F 109.5 . . ?
C415 C418 H41G 109.5 . . ?
C415 C418 H41H 109.5 . . ?
H41G C418 H41H 109.5 . . ?
C415 C418 H41I 109.5 . . ?
H41G C418 H41I 109.5 . . ?
H41H C418 H41I 109.5 . . ?
C415 C419 H41J 109.5 . . ?
C415 C419 H41K 109.5 . . ?
H41J C419 H41K 109.5 . . ?
C415 C419 H41L 109.5 . . ?
H41J C419 H41L 109.5 . . ?
H41K C419 H41L 109.5 . . ?
B4 O61 C614 106.8(3) . . ?
B4 O62 C615 105.7(3) . . ?
O61 C614 C616 109.2(5) . . ?
O61 C614 C617 104.5(4) . . ?
C616 C614 C617 108.0(5) . . ?
O61 C614 C615 106.5(4) . . ?
C616 C614 C615 116.7(5) . . ?
C617 C614 C615 111.2(4) . . ?
C619 C615 O62 108.9(4) . . ?
C619 C615 C614 133.3(5) . . ?
O62 C615 C614 103.8(4) . . ?
C619 C615 C618 105.6(5) . . ?
O62 C615 C618 98.2(4) . . ?
C614 C615 C618 101.5(4) . . ?
C614 C616 H61A 109.5 . . ?
C614 C616 H61B 109.5 . . ?
H61A C616 H61B 109.5 . . ?
C614 C616 H61C 109.5 . . ?
H61A C616 H61C 109.5 . . ?
H61B C616 H61C 109.5 . . ?
C614 C617 H61D 109.5 . . ?
C614 C617 H61E 109.5 . . ?
H61D C617 H61E 109.5 . . ?
C614 C617 H61F 109.5 . . ?
H61D C617 H61F 109.5 . . ?
H61E C617 H61F 109.5 . . ?
C615 C618 H61G 109.5 . . ?
C615 C618 H61H 109.5 . . ?
H61G C618 H61H 109.5 . . ?
C615 C618 H61I 109.5 . . ?
H61G C618 H61I 109.5 . . ?
H61H C618 H61I 109.5 . . ?
C615 C619 H61J 109.5 . . ?
C615 C619 H61K 109.5 . . ?
H61J C619 H61K 109.5 . . ?
C615 C619 H61L 109.5 . . ?
H61J C619 H61L 109.5 . . ?
H61K C619 H61L 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
N1 C11 P1 C18 158.19(14) . . . . ?
S1 C11 P1 C18 -22.57(14) . . . . ?
N1 C11 P1 C12 -93.97(14) . . . . ?
S1 C11 P1 C12 85.28(13) . . . . ?
S1 C11 N1 B1 165.87(15) . . . . ?
P1 C11 N1 B1 -15.0(2) . . . . ?
S1 C11 N1 C120 -6.8(3) . . . . ?
P1 C11 N1 C120 172.42(15) . . . . ?
C11 N1 B1 O11 93.8(2) . . . . ?
C120 N1 B1 O11 -93.0(2) . . . . ?
C11 N1 B1 O12 -91.8(2) . . . . ?
C120 N1 B1 O12 81.4(2) . . . . ?
O12 B1 O11 C114 -4.3(2) . . . . ?
N1 B1 O11 C114 170.43(18) . . . . ?
O11 B1 O12 C115 -9.6(2) . . . . ?
N1 B1 O12 C115 175.58(17) . . . . ?
C18 P1 C12 C13 84.42(19) . . . . ?
C11 P1 C12 C13 -22.84(19) . . . . ?
C18 P1 C12 C17 -96.05(16) . . . . ?
C11 P1 C12 C17 156.69(16) . . . . ?
C17 C12 C13 C14 -0.7(3) . . . . ?
P1 C12 C13 C14 178.78(18) . . . . ?
C12 C13 C14 C15 1.5(4) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C15 C16 C17 C12 1.2(4) . . . . ?
C13 C12 C17 C16 -0.6(3) . . . . ?
P1 C12 C17 C16 179.86(18) . . . . ?
C12 P1 C18 C19 -1.2(2) . . . . ?
C11 P1 C18 C19 103.82(18) . . . . ?
C12 P1 C18 C113 172.40(18) . . . . ?
C11 P1 C18 C113 -82.56(19) . . . . ?
C113 C18 C19 C110 0.3(3) . . . . ?
P1 C18 C19 C110 173.81(17) . . . . ?
C18 C19 C110 C111 0.6(4) . . . . ?
C19 C110 C111 C112 -0.3(4) . . . . ?
C110 C111 C112 C113 -0.8(4) . . . . ?
C111 C112 C113 C18 1.7(4) . . . . ?
C19 C18 C113 C112 -1.5(4) . . . . ?
P1 C18 C113 C112 -175.5(2) . . . . ?
C11 N1 C120 C121 -172.3(2) . . . . ?
B1 N1 C120 C121 14.9(3) . . . . ?
C11 N1 C120 C122 68.6(3) . . . . ?
B1 N1 C120 C122 -104.2(2) . . . . ?
C11 N1 C120 C123 -55.7(3) . . . . ?
B1 N1 C120 C123 131.5(2) . . . . ?
B1 O11 C114 C117 137.3(2) . . . . ?
B1 O11 C114 C116 -104.6(2) . . . . ?
B1 O11 C114 C115 15.2(2) . . . . ?
B1 O12 C115 C118 141.28(18) . . . . ?
B1 O12 C115 C119 -101.02(18) . . . . ?
B1 O12 C115 C114 18.0(2) . . . . ?
O11 C114 C115 O12 -20.0(2) . . . . ?
C117 C114 C115 O12 -137.6(2) . . . . ?
C116 C114 C115 O12 94.4(2) . . . . ?
O11 C114 C115 C118 -138.5(2) . . . . ?
C117 C114 C115 C118 103.8(3) . . . . ?
C116 C114 C115 C118 -24.2(3) . . . . ?
O11 C114 C115 C119 93.4(2) . . . . ?
C117 C114 C115 C119 -24.3(3) . . . . ?
C116 C114 C115 C119 -152.3(2) . . . . ?
N2 C21 P2 C28 -162.95(14) . . . . ?
S2 C21 P2 C28 18.11(16) . . . . ?
N2 C21 P2 C22 89.04(15) . . . . ?
S2 C21 P2 C22 -89.90(14) . . . . ?
S2 C21 N2 B2 -159.40(17) . . . . ?
P2 C21 N2 B2 21.8(2) . . . . ?
S2 C21 N2 C220 8.2(3) . . . . ?
P2 C21 N2 C220 -170.63(15) . . . . ?
C21 N2 B2 O21 -97.8(2) . . . . ?
C220 N2 B2 O21 93.7(2) . . . . ?
C21 N2 B2 O22 87.9(2) . . . . ?
C220 N2 B2 O22 -80.6(2) . . . . ?
O22 B2 O21 C214 3.2(2) . . . . ?
N2 B2 O21 C214 -171.34(18) . . . . ?
O21 B2 O22 C215 10.2(2) . . . . ?
N2 B2 O22 C215 -174.97(16) . . . . ?
C28 P2 C22 C27 97.17(17) . . . . ?
C21 P2 C22 C27 -155.93(16) . . . . ?
C28 P2 C22 C23 -84.57(19) . . . . ?
C21 P2 C22 C23 22.33(19) . . . . ?
C27 C22 C23 C24 0.6(3) . . . . ?
P2 C22 C23 C24 -177.62(18) . . . . ?
C22 C23 C24 C25 -1.2(4) . . . . ?
C23 C24 C25 C26 0.4(4) . . . . ?
C24 C25 C26 C27 0.8(4) . . . . ?
C25 C26 C27 C22 -1.3(4) . . . . ?
C23 C22 C27 C26 0.6(3) . . . . ?
P2 C22 C27 C26 178.98(18) . . . . ?
C22 P2 C28 C29 4.4(2) . . . . ?
C21 P2 C28 C29 -100.40(19) . . . . ?
C22 P2 C28 C213 -170.42(17) . . . . ?
C21 P2 C28 C213 84.77(18) . . . . ?
C213 C28 C29 C210 -0.7(3) . . . . ?
P2 C28 C29 C210 -175.36(18) . . . . ?
C28 C29 C210 C211 -1.0(4) . . . . ?
C29 C210 C211 C212 1.2(4) . . . . ?
C210 C211 C212 C213 0.3(4) . . . . ?
C211 C212 C213 C28 -2.0(4) . . . . ?
C29 C28 C213 C212 2.2(4) . . . . ?
P2 C28 C213 C212 177.3(2) . . . . ?
C21 N2 C220 C222 -67.5(3) . . . . ?
B2 N2 C220 C222 100.4(3) . . . . ?
C21 N2 C220 C223 57.6(3) . . . . ?
B2 N2 C220 C223 -134.6(2) . . . . ?
C21 N2 C220 C221 173.8(2) . . . . ?
B2 N2 C220 C221 -18.4(3) . . . . ?
B2 O21 C214 C216 -136.2(2) . . . . ?
B2 O21 C214 C217 105.4(2) . . . . ?
B2 O21 C214 C215 -13.9(2) . . . . ?
B2 O22 C215 C219 -141.05(19) . . . . ?
B2 O22 C215 C218 101.32(19) . . . . ?
B2 O22 C215 C214 -17.7(2) . . . . ?
O21 C214 C215 O22 19.0(2) . . . . ?
C216 C214 C215 O22 136.7(2) . . . . ?
C217 C214 C215 O22 -95.4(2) . . . . ?
O21 C214 C215 C219 137.5(2) . . . . ?
C216 C214 C215 C219 -104.9(3) . . . . ?
C217 C214 C215 C219 23.0(3) . . . . ?
O21 C214 C215 C218 -94.3(2) . . . . ?
C216 C214 C215 C218 23.3(3) . . . . ?
C217 C214 C215 C218 151.2(2) . . . . ?
N3 C31 P3 C38 -156.56(14) . . . . ?
S3 C31 P3 C38 24.79(15) . . . . ?
N3 C31 P3 C32 96.31(14) . . . . ?
S3 C31 P3 C32 -82.34(14) . . . . ?
S3 C31 N3 B3 -165.18(15) . . . . ?
P3 C31 N3 B3 16.3(2) . . . . ?
S3 C31 N3 C320 8.9(3) . . . . ?
P3 C31 N3 C320 -169.62(14) . . . . ?
C31 N3 B3 O31 -94.3(15) . . . . ?
C320 N3 B3 O31 91.2(15) . . . . ?
C31 N3 B3 O32 97.2(7) . . . . ?
C320 N3 B3 O32 -77.3(7) . . . . ?
C31 N3 B3 O52 82.8(4) . . . . ?
C320 N3 B3 O52 -91.7(4) . . . . ?
C31 N3 B3 O51 -99.9(8) . . . . ?
C320 N3 B3 O51 85.6(8) . . . . ?
C38 P3 C32 C37 -83.46(19) . . . . ?
C31 P3 C32 C37 23.5(2) . . . . ?
C38 P3 C32 C33 96.75(16) . . . . ?
C31 P3 C32 C33 -156.31(15) . . . . ?
C37 C32 C33 C34 1.6(3) . . . . ?
P3 C32 C33 C34 -178.57(16) . . . . ?
C32 C33 C34 C35 -1.5(3) . . . . ?
C33 C34 C35 C36 0.3(4) . . . . ?
C34 C35 C36 C37 0.6(4) . . . . ?
C35 C36 C37 C32 -0.4(4) . . . . ?
C33 C32 C37 C36 -0.7(3) . . . . ?
P3 C32 C37 C36 179.51(18) . . . . ?
C32 P3 C38 C313 -5.77(19) . . . . ?
C31 P3 C38 C313 -111.33(18) . . . . ?
C32 P3 C38 C39 -179.76(17) . . . . ?
C31 P3 C38 C39 74.68(19) . . . . ?
C313 C38 C39 C310 0.3(4) . . . . ?
P3 C38 C39 C310 174.6(2) . . . . ?
C38 C39 C310 C311 -0.8(4) . . . . ?
C39 C310 C311 C312 0.7(4) . . . . ?
C310 C311 C312 C313 -0.1(4) . . . . ?
C39 C38 C313 C312 0.3(3) . . . . ?
P3 C38 C313 C312 -173.64(17) . . . . ?
C311 C312 C313 C38 -0.4(3) . . . . ?
C31 N3 C320 C323 -64.3(3) . . . . ?
B3 N3 C320 C323 109.8(2) . . . . ?
C31 N3 C320 C322 59.6(3) . . . . ?
B3 N3 C320 C322 -126.19(19) . . . . ?
C31 N3 C320 C321 177.1(2) . . . . ?
B3 N3 C320 C321 -8.8(2) . . . . ?
O32 B3 O31 C314 0(3) . . . . ?
N3 B3 O31 C314 -168.9(13) . . . . ?
O31 B3 O32 C315 11.0(19) . . . . ?
N3 B3 O32 C315 -179.6(11) . . . . ?
B3 O31 C314 C317 -131(2) . . . . ?
B3 O31 C314 C316 102(2) . . . . ?
B3 O31 C314 C315 -12(3) . . . . ?
C317 C314 C315 C319 -107(2) . . . . ?
C316 C314 C315 C319 27(3) . . . . ?
O31 C314 C315 C319 137(2) . . . . ?
C317 C314 C315 O32 132.7(18) . . . . ?
C316 C314 C315 O32 -93(2) . . . . ?
O31 C314 C315 O32 17(2) . . . . ?
C317 C314 C315 C318 21(3) . . . . ?
C316 C314 C315 C318 155.4(17) . . . . ?
O31 C314 C315 C318 -95(2) . . . . ?
B3 O32 C315 C314 -19(2) . . . . ?
B3 O32 C315 C319 -149.5(11) . . . . ?
B3 O32 C315 C318 103.2(10) . . . . ?
O52 B3 O51 C514 -4.2(13) . . . . ?
N3 B3 O51 C514 178.4(7) . . . . ?
O51 B3 O52 C515 -6.3(12) . . . . ?
N3 B3 O52 C515 171.3(7) . . . . ?
B3 O51 C514 C517 -109.6(10) . . . . ?
B3 O51 C514 C516 136.1(10) . . . . ?
B3 O51 C514 C515 11.7(14) . . . . ?
B3 O52 C515 C519 134.1(6) . . . . ?
B3 O52 C515 C518 -103.1(7) . . . . ?
B3 O52 C515 C514 12.3(12) . . . . ?
O51 C514 C515 O52 -15.3(14) . . . . ?
C517 C514 C515 O52 101.4(11) . . . . ?
C516 C514 C515 O52 -133.5(11) . . . . ?
O51 C514 C515 C519 -134.3(12) . . . . ?
C517 C514 C515 C519 -17.6(15) . . . . ?
C516 C514 C515 C519 107.5(13) . . . . ?
O51 C514 C515 C518 99.7(12) . . . . ?
C517 C514 C515 C518 -143.7(9) . . . . ?
C516 C514 C515 C518 -18.5(16) . . . . ?
N4 C41 P4 C42 157.15(14) . . . . ?
S4 C41 P4 C42 -24.70(15) . . . . ?
N4 C41 P4 C48 -95.54(14) . . . . ?
S4 C41 P4 C48 82.61(13) . . . . ?
S4 C41 N4 B4 164.97(15) . . . . ?
P4 C41 N4 B4 -17.1(2) . . . . ?
S4 C41 N4 C420 -9.2(3) . . . . ?
P4 C41 N4 C420 168.81(14) . . . . ?
O41 B4 N4 C41 104.5(3) . . . . ?
O42 B4 N4 C41 -94.5(3) . . . . ?
O62 B4 N4 C41 -81.3(3) . . . . ?
O61 B4 N4 C41 93.0(3) . . . . ?
O41 B4 N4 C420 -80.9(3) . . . . ?
O42 B4 N4 C420 80.0(3) . . . . ?
O62 B4 N4 C420 93.3(3) . . . . ?
O61 B4 N4 C420 -92.5(3) . . . . ?
C48 P4 C42 C47 3.71(19) . . . . ?
C41 P4 C42 C47 109.29(18) . . . . ?
C48 P4 C42 C43 177.97(17) . . . . ?
C41 P4 C42 C43 -76.45(18) . . . . ?
C47 C42 C43 C44 0.0(3) . . . . ?
P4 C42 C43 C44 -174.58(19) . . . . ?
C42 C43 C44 C45 0.9(4) . . . . ?
C43 C44 C45 C46 -0.8(4) . . . . ?
C44 C45 C46 C47 -0.2(4) . . . . ?
C45 C46 C47 C42 1.1(4) . . . . ?
C43 C42 C47 C46 -1.0(3) . . . . ?
P4 C42 C47 C46 173.22(17) . . . . ?
C42 P4 C48 C49 83.18(19) . . . . ?
C41 P4 C48 C49 -23.8(2) . . . . ?
C42 P4 C48 C413 -96.72(16) . . . . ?
C41 P4 C48 C413 156.32(15) . . . . ?
C413 C48 C49 C410 0.5(3) . . . . ?
P4 C48 C49 C410 -179.41(18) . . . . ?
C48 C49 C410 C411 0.5(4) . . . . ?
C49 C410 C411 C412 -0.6(4) . . . . ?
C410 C411 C412 C413 -0.2(4) . . . . ?
C411 C412 C413 C48 1.2(3) . . . . ?
C49 C48 C413 C412 -1.3(3) . . . . ?
P4 C48 C413 C412 178.57(16) . . . . ?
C41 N4 C420 C423 64.4(3) . . . . ?
B4 N4 C420 C423 -109.8(2) . . . . ?
C41 N4 C420 C422 -59.4(3) . . . . ?
B4 N4 C420 C422 126.3(2) . . . . ?
C41 N4 C420 C421 -176.8(2) . . . . ?
B4 N4 C420 C421 8.9(3) . . . . ?
O42 B4 O41 C414 23.5(5) . . . . ?
N4 B4 O41 C414 -174.4(3) . . . . ?
O41 B4 O42 C415 -13.1(5) . . . . ?
N4 B4 O42 C415 -175.6(3) . . . . ?
B4 O41 C414 C417 100.0(5) . . . . ?
B4 O41 C414 C416 -139.1(5) . . . . ?
B4 O41 C414 C415 -22.1(5) . . . . ?
B4 O42 C415 C418 140.8(6) . . . . ?
B4 O42 C415 C414 -3.1(5) . . . . ?
B4 O42 C415 C419 -98.6(5) . . . . ?
C417 C414 C415 C418 116.1(7) . . . . ?
C416 C414 C415 C418 -16.6(8) . . . . ?
O41 C414 C415 C418 -128.3(6) . . . . ?
C417 C414 C415 O42 -101.0(6) . . . . ?
C416 C414 C415 O42 126.2(5) . . . . ?
O41 C414 C415 O42 14.5(5) . . . . ?
C417 C414 C415 C419 0.9(6) . . . . ?
C416 C414 C415 C419 -131.8(5) . . . . ?
O41 C414 C415 C419 116.5(4) . . . . ?
O62 B4 O61 C614 -16.5(4) . . . . ?
N4 B4 O61 C614 168.9(3) . . . . ?
O61 B4 O62 C615 8.5(4) . . . . ?
N4 B4 O62 C615 -176.7(3) . . . . ?
B4 O61 C614 C616 -110.4(5) . . . . ?
B4 O61 C614 C617 134.2(4) . . . . ?
B4 O61 C614 C615 16.4(5) . . . . ?
B4 O62 C615 C619 -144.3(4) . . . . ?
B4 O62 C615 C614 2.0(4) . . . . ?
B4 O62 C615 C618 106.1(4) . . . . ?
O61 C614 C615 C619 122.3(6) . . . . ?
C616 C614 C615 C619 -115.4(7) . . . . ?
C617 C614 C615 C619 9.0(8) . . . . ?
O61 C614 C615 O62 -11.5(5) . . . . ?
C616 C614 C615 O62 110.8(5) . . . . ?
C617 C614 C615 O62 -124.8(4) . . . . ?
O61 C614 C615 C618 -113.0(4) . . . . ?
C616 C614 C615 C618 9.2(6) . . . . ?
C617 C614 C615 C618 133.7(5) . . . . ?

_refine_diff_density_max         1.247
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.065

