# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

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

data_erk9523
_database_code_depnum_ccdc_archive 'CCDC 1953115'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-09-12 deposited with the CCDC.	2020-06-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H31 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         398.50

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0785(3)
_cell_length_b                   10.6049(4)
_cell_length_c                   13.1636(5)
_cell_angle_alpha                94.492(2)
_cell_angle_beta                 96.6290(10)
_cell_angle_gamma                110.7610(10)
_cell_volume                     1167.39(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      2.5482
_cell_measurement_theta_max      27.4505
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.162
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428

_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            21644
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_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

_refine_special_details          
;

Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             5318
_reflns_number_gt                4688
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1103
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_number_reflns         5318
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²+0.7889P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.58747(4) 0.34791(4) 0.72855(3) 0.01550(10) Uani d . . . 1 . .
C C1 0.50144(17) 0.45662(15) 0.66365(12) 0.0182(3) Uani d . . . 1 . .
H H1 0.4416 0.4266 0.5964 0.022 Uiso calc U . R 1 . .
C C2 0.5231(2) 0.57815(17) 0.71116(14) 0.0276(4) Uani d . . . 1 . .
H H2A 0.5831 0.6077 0.7784 0.033 Uiso calc U . R 1 . .
H H2B 0.4787 0.6358 0.678 0.033 Uiso calc U . R 1 . .
C C3 0.64291(18) 0.26521(16) 0.62174(13) 0.0218(3) Uani d . . . 1 . .
H H3 0.6542 0.181 0.631 0.026 Uiso calc U . R 1 . .
C C4 0.6694(2) 0.31053(18) 0.53188(13) 0.0262(3) Uani d . . . 1 . .
H H4A 0.6597 0.3943 0.5188 0.031 Uiso calc U . R 1 . .
H H4B 0.698 0.2592 0.4806 0.031 Uiso calc U . R 1 . .
C C11 0.42003(17) 0.20459(14) 0.76296(11) 0.0142(3) Uani d . . . 1 . .
C C12 0.46109(17) 0.14305(14) 0.84789(11) 0.0157(3) Uani d . . . 1 . .
C C13 0.34359(18) 0.03871(15) 0.88400(12) 0.0196(3) Uani d . . . 1 . .
H H13 0.3722 -0.0026 0.9407 0.024 Uiso calc U . R 1 . .
C C14 0.18599(19) -0.00513(16) 0.83808(13) 0.0235(3) Uani d . . . 1 . .
H H14 0.1063 -0.0746 0.8641 0.028 Uiso calc U . R 1 . .
C C15 0.14521(18) 0.05291(16) 0.75388(12) 0.0201(3) Uani d . . . 1 . .
H H15 0.037 0.0221 0.7222 0.024 Uiso calc U . R 1 . .
C C16 0.25991(17) 0.15567(14) 0.71470(11) 0.0155(3) Uani d . . . 1 . .
C C21 0.63035(17) 0.18382(15) 0.89962(11) 0.0158(3) Uani d . . . 1 . .
C C22 0.72114(19) 0.10703(16) 0.87266(11) 0.0201(3) Uani d . . . 1 . .
C C23 0.87879(19) 0.14765(18) 0.92063(13) 0.0249(3) Uani d . . . 1 . .
H H23 0.9409 0.0964 0.902 0.03 Uiso calc U . R 1 . .
C C24 0.94782(18) 0.26083(18) 0.99491(13) 0.0253(4) Uani d . . . 1 . .
C C25 0.85394(19) 0.33212(17) 1.02366(12) 0.0232(3) Uani d . . . 1 . .
H H25 0.8985 0.4081 1.0759 0.028 Uiso calc U . R 1 . .
C C26 0.69570(18) 0.29481(15) 0.97767(11) 0.0187(3) Uani d . . . 1 . .
C C27 0.6497(2) -0.02080(19) 0.79595(13) 0.0303(4) Uani d . . . 1 . .
H H27A 0.5789 -0.0941 0.8283 0.045 Uiso calc U . R 1 . .
H H27B 0.7353 -0.0474 0.7741 0.045 Uiso calc U . R 1 . .
H H27C 0.5888 -0.0036 0.7358 0.045 Uiso calc U . R 1 . .
C C28 1.1200(2) 0.3030(2) 1.04419(16) 0.0370(5) Uani d . . . 1 . .
H H28A 1.154 0.3926 1.085 0.056 Uiso calc U . R 1 . .
H H28B 1.187 0.3074 0.9903 0.056 Uiso calc U . R 1 . .
H H28C 1.1304 0.2363 1.0892 0.056 Uiso calc U . R 1 . .
C C29 0.5955(2) 0.37310(17) 1.01094(13) 0.0250(3) Uani d . . . 1 . .
H H29A 0.5666 0.4175 0.9534 0.037 Uiso calc U . R 1 . .
H H29B 0.6564 0.4421 1.0694 0.037 Uiso calc U . R 1 . .
H H29C 0.4984 0.3105 1.0316 0.037 Uiso calc U . R 1 . .
C C31 0.20386(16) 0.20454(14) 0.61935(11) 0.0149(3) Uani d . . . 1 . .
C C32 0.21917(17) 0.14952(14) 0.52257(11) 0.0171(3) Uani d . . . 1 . .
C C33 0.17027(18) 0.19880(15) 0.43487(11) 0.0186(3) Uani d . . . 1 . .
H H33 0.1862 0.1655 0.3696 0.022 Uiso calc U . R 1 . .
C C34 0.09907(17) 0.29498(15) 0.43974(11) 0.0186(3) Uani d . . . 1 . .
C C35 0.07878(17) 0.34362(15) 0.53643(12) 0.0182(3) Uani d . . . 1 . .
H H35 0.0284 0.4081 0.5411 0.022 Uiso calc U . R 1 . .
C C36 0.13013(17) 0.30064(15) 0.62632(11) 0.0162(3) Uani d . . . 1 . .
C C37 0.27791(19) 0.03319(16) 0.51027(12) 0.0222(3) Uani d . . . 1 . .
H H37A 0.1865 -0.0531 0.4959 0.033 Uiso calc U . R 1 . .
H H37B 0.3458 0.0338 0.574 0.033 Uiso calc U . R 1 . .
H H37C 0.3395 0.0435 0.453 0.033 Uiso calc U . R 1 . .
C C38 0.0424(2) 0.34260(17) 0.34294(12) 0.0248(3) Uani d . . . 1 . .
H H38A 0.1062 0.4389 0.3426 0.037 Uiso calc U . R 1 . .
H H38B -0.07 0.3309 0.3409 0.037 Uiso calc U . R 1 . .
H H38C 0.0541 0.289 0.2824 0.037 Uiso calc U . R 1 . .
C C39 0.1076(2) 0.35838(17) 0.72919(12) 0.0225(3) Uani d . . . 1 . .
H H39A 0.0719 0.4344 0.72 0.034 Uiso calc U . R 1 . .
H H39B 0.2089 0.3907 0.7764 0.034 Uiso calc U . R 1 . .
H H39C 0.0273 0.2876 0.7581 0.034 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C3 . 1.8118(16) ?
P1 C1 . 1.8186(15) ?
P1 C11 . 1.8587(14) ?
C1 C2 . 1.325(2) ?
C1 H1 . 0.95 ?
C2 H2A . 0.95 ?
C2 H2B . 0.95 ?
C3 C4 . 1.327(2) ?
C3 H3 . 0.95 ?
C4 H4A . 0.95 ?
C4 H4B . 0.95 ?
C11 C16 . 1.4095(19) ?
C11 C12 . 1.4160(19) ?
C12 C13 . 1.397(2) ?
C12 C21 . 1.5011(19) ?
C13 C14 . 1.383(2) ?
C13 H13 . 0.95 ?
C14 C15 . 1.385(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.395(2) ?
C15 H15 . 0.95 ?
C16 C31 . 1.4980(19) ?
C21 C22 . 1.402(2) ?
C21 C26 . 1.403(2) ?
C22 C23 . 1.394(2) ?
C22 C27 . 1.513(2) ?
C23 C24 . 1.390(3) ?
C23 H23 . 0.95 ?
C24 C25 . 1.388(2) ?
C24 C28 . 1.513(2) ?
C25 C26 . 1.395(2) ?
C25 H25 . 0.95 ?
C26 C29 . 1.510(2) ?
C27 H27A . 0.98 ?
C27 H27B . 0.98 ?
C27 H27C . 0.98 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C29 H29A . 0.98 ?
C29 H29B . 0.98 ?
C29 H29C . 0.98 ?
C31 C32 . 1.402(2) ?
C31 C36 . 1.406(2) ?
C32 C33 . 1.394(2) ?
C32 C37 . 1.512(2) ?
C33 C34 . 1.389(2) ?
C33 H33 . 0.95 ?
C34 C35 . 1.392(2) ?
C34 C38 . 1.509(2) ?
C35 C36 . 1.390(2) ?
C35 H35 . 0.95 ?
C36 C39 . 1.508(2) ?
C37 H37A . 0.98 ?
C37 H37B . 0.98 ?
C37 H37C . 0.98 ?
C38 H38A . 0.98 ?
C38 H38B . 0.98 ?
C38 H38C . 0.98 ?
C39 H39A . 0.98 ?
C39 H39B . 0.98 ?
C39 H39C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 P1 C1 . . 101.56(7) ?
C3 P1 C11 . . 101.64(7) ?
C1 P1 C11 . . 107.27(7) ?
C2 C1 P1 . . 119.31(12) ?
C2 C1 H1 . . 120.3 ?
P1 C1 H1 . . 120.3 ?
C1 C2 H2A . . 120.0 ?
C1 C2 H2B . . 120.0 ?
H2A C2 H2B . . 120.0 ?
C4 C3 P1 . . 126.53(13) ?
C4 C3 H3 . . 116.7 ?
P1 C3 H3 . . 116.7 ?
C3 C4 H4A . . 120.0 ?
C3 C4 H4B . . 120.0 ?
H4A C4 H4B . . 120.0 ?
C16 C11 C12 . . 118.53(13) ?
C16 C11 P1 . . 126.41(10) ?
C12 C11 P1 . . 115.04(10) ?
C13 C12 C11 . . 120.16(13) ?
C13 C12 C21 . . 118.03(13) ?
C11 C12 C21 . . 121.78(12) ?
C14 C13 C12 . . 120.67(14) ?
C14 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
C13 C14 C15 . . 119.54(14) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
C14 C15 C16 . . 121.29(14) ?
C14 C15 H15 . . 119.4 ?
C16 C15 H15 . . 119.4 ?
C15 C16 C11 . . 119.74(13) ?
C15 C16 C31 . . 116.62(13) ?
C11 C16 C31 . . 123.60(12) ?
C22 C21 C26 . . 119.94(14) ?
C22 C21 C12 . . 119.72(13) ?
C26 C21 C12 . . 120.28(13) ?
C23 C22 C21 . . 118.83(15) ?
C23 C22 C27 . . 119.77(14) ?
C21 C22 C27 . . 121.36(14) ?
C24 C23 C22 . . 122.01(15) ?
C24 C23 H23 . . 119.0 ?
C22 C23 H23 . . 119.0 ?
C25 C24 C23 . . 118.26(14) ?
C25 C24 C28 . . 121.22(17) ?
C23 C24 C28 . . 120.51(16) ?
C24 C25 C26 . . 121.52(15) ?
C24 C25 H25 . . 119.2 ?
C26 C25 H25 . . 119.2 ?
C25 C26 C21 . . 119.32(14) ?
C25 C26 C29 . . 120.55(14) ?
C21 C26 C29 . . 120.13(13) ?
C22 C27 H27A . . 109.5 ?
C22 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C22 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C24 C28 H28A . . 109.5 ?
C24 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C24 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C26 C29 H29A . . 109.5 ?
C26 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
C26 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
C32 C31 C36 . . 120.05(13) ?
C32 C31 C16 . . 119.52(13) ?
C36 C31 C16 . . 120.37(13) ?
C33 C32 C31 . . 118.73(13) ?
C33 C32 C37 . . 119.22(13) ?
C31 C32 C37 . . 121.95(13) ?
C34 C33 C32 . . 122.24(14) ?
C34 C33 H33 . . 118.9 ?
C32 C33 H33 . . 118.9 ?
C33 C34 C35 . . 117.86(13) ?
C33 C34 C38 . . 120.90(14) ?
C35 C34 C38 . . 121.23(14) ?
C36 C35 C34 . . 121.95(14) ?
C36 C35 H35 . . 119.0 ?
C34 C35 H35 . . 119.0 ?
C35 C36 C31 . . 119.05(13) ?
C35 C36 C39 . . 119.75(13) ?
C31 C36 C39 . . 121.20(13) ?
C32 C37 H37A . . 109.5 ?
C32 C37 H37B . . 109.5 ?
H37A C37 H37B . . 109.5 ?
C32 C37 H37C . . 109.5 ?
H37A C37 H37C . . 109.5 ?
H37B C37 H37C . . 109.5 ?
C34 C38 H38A . . 109.5 ?
C34 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C34 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C36 C39 H39A . . 109.5 ?
C36 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C36 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 P1 C1 C2 . . . . -144.18(14) ?
C11 P1 C1 C2 . . . . 109.60(14) ?
C1 P1 C3 C4 . . . . 22.47(17) ?
C11 P1 C3 C4 . . . . 133.04(15) ?
C3 P1 C11 C16 . . . . -82.48(13) ?
C1 P1 C11 C16 . . . . 23.68(14) ?
C3 P1 C11 C12 . . . . 99.09(12) ?
C1 P1 C11 C12 . . . . -154.74(11) ?
C16 C11 C12 C13 . . . . -1.7(2) ?
P1 C11 C12 C13 . . . . 176.87(11) ?
C16 C11 C12 C21 . . . . 176.45(13) ?
P1 C11 C12 C21 . . . . -4.99(18) ?
C11 C12 C13 C14 . . . . -0.5(2) ?
C21 C12 C13 C14 . . . . -178.70(14) ?
C12 C13 C14 C15 . . . . 1.6(2) ?
C13 C14 C15 C16 . . . . -0.5(2) ?
C14 C15 C16 C11 . . . . -1.8(2) ?
C14 C15 C16 C31 . . . . 176.16(14) ?
C12 C11 C16 C15 . . . . 2.8(2) ?
P1 C11 C16 C15 . . . . -175.59(11) ?
C12 C11 C16 C31 . . . . -174.98(13) ?
P1 C11 C16 C31 . . . . 6.6(2) ?
C13 C12 C21 C22 . . . . 80.97(18) ?
C11 C12 C21 C22 . . . . -97.20(17) ?
C13 C12 C21 C26 . . . . -96.37(17) ?
C11 C12 C21 C26 . . . . 85.45(18) ?
C26 C21 C22 C23 . . . . -3.5(2) ?
C12 C21 C22 C23 . . . . 179.16(13) ?
C26 C21 C22 C27 . . . . 174.30(14) ?
C12 C21 C22 C27 . . . . -3.1(2) ?
C21 C22 C23 C24 . . . . 0.7(2) ?
C27 C22 C23 C24 . . . . -177.14(15) ?
C22 C23 C24 C25 . . . . 2.0(2) ?
C22 C23 C24 C28 . . . . -179.12(14) ?
C23 C24 C25 C26 . . . . -1.9(2) ?
C28 C24 C25 C26 . . . . 179.22(15) ?
C24 C25 C26 C21 . . . . -0.8(2) ?
C24 C25 C26 C29 . . . . 179.41(14) ?
C22 C21 C26 C25 . . . . 3.6(2) ?
C12 C21 C26 C25 . . . . -179.08(13) ?
C22 C21 C26 C29 . . . . -176.68(14) ?
C12 C21 C26 C29 . . . . 0.7(2) ?
C15 C16 C31 C32 . . . . -95.38(17) ?
C11 C16 C31 C32 . . . . 82.44(18) ?
C15 C16 C31 C36 . . . . 81.90(17) ?
C11 C16 C31 C36 . . . . -100.27(17) ?
C36 C31 C32 C33 . . . . 4.4(2) ?
C16 C31 C32 C33 . . . . -178.31(13) ?
C36 C31 C32 C37 . . . . -171.97(13) ?
C16 C31 C32 C37 . . . . 5.3(2) ?
C31 C32 C33 C34 . . . . -3.6(2) ?
C37 C32 C33 C34 . . . . 172.87(14) ?
C32 C33 C34 C35 . . . . 0.8(2) ?
C32 C33 C34 C38 . . . . -177.86(14) ?
C33 C34 C35 C36 . . . . 1.3(2) ?
C38 C34 C35 C36 . . . . 179.91(14) ?
C34 C35 C36 C31 . . . . -0.4(2) ?
C34 C35 C36 C39 . . . . 178.99(14) ?
C32 C31 C36 C35 . . . . -2.5(2) ?
C16 C31 C36 C35 . . . . -179.73(13) ?
C32 C31 C36 C39 . . . . 178.15(13) ?
C16 C31 C36 C39 . . . . 0.9(2) ?


####################################################################### 
# 
# 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_erk9477
_database_code_depnum_ccdc_archive 'CCDC 1953116'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-09-12 deposited with the CCDC.	2020-06-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C49 H41 B F10 N P'
_chemical_formula_iupac          ?
_chemical_formula_weight         875.61

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.3195(4)
_cell_length_b                   12.0466(3)
_cell_length_c                   19.8048(8)
_cell_angle_alpha                78.2740(10)
_cell_angle_beta                 83.6580(10)
_cell_angle_gamma                79.969(3)
_cell_volume                     2595.93(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5628
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904

_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'Mo rotating anode'
_diffrn_source_type              'Mo rotating anode'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Montel mirror'

_diffrn_measurement_device_type  'rotating anode Nonius FR591'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            21730
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23

_refine_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.

A mixture of badly disordered pentane and dichloromethane
molecules was found in the asymmetrical unit and could not be 
satisfactorily refined. The program SQUEEZE (Spek, A.L. (2015). 
Acta Cryst. C71, 9-18.) was therefore used to remove mathematically
the effect of the solvent.
The quoted formula and derived parameters are not included the squeezed
solvent molecules. 

One C6F5 group is disordered over two positions. Several restraints (SADI,
SAME, ISOR and SIMU) were used in order to improve refinement stability.
;


_reflns_number_total             8847
_reflns_number_gt                6757
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0756
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.1829
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.063
_refine_ls_number_reflns         8847
_refine_ls_number_parameters     667
_refine_ls_number_restraints     230
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+4.4798P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.298
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;

Collect (Nonius B.V., 1998)
;
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.27527(8) 0.64426(7) 0.24267(4) 0.0337(2) Uani d . . . 1.0 . .
C C1 0.2106(3) 0.7743(3) 0.27930(17) 0.0386(8) Uani d . . . 1.0 . .
H H1A 0.1253 0.7719 0.2962 0.046 Uiso calc U . R 1.0 . .
H H1B 0.2558 0.779 0.3184 0.046 Uiso calc U . R 1.0 . .
C C2 0.2211(3) 0.8799(3) 0.21970(17) 0.0370(8) Uani d . . . 1.0 . .
H H2 0.1384 0.9249 0.215 0.044 Uiso calc U . R 1.0 . .
C C4 0.2208(4) 0.7183(3) 0.15762(17) 0.0432(9) Uani d . . . 1.0 . .
H H4A 0.2597 0.6786 0.1199 0.052 Uiso calc U . R 1.0 . .
H H4B 0.1323 0.7252 0.1579 0.052 Uiso calc U . R 1.0 . .
C C3 0.2603(4) 0.8352(3) 0.15140(18) 0.0476(9) Uani d . . . 1.0 . .
H H3A 0.2229 0.89 0.1124 0.057 Uiso calc U . R 1.0 . .
H H3B 0.3488 0.8279 0.1423 0.057 Uiso calc U . R 1.0 . .
C C11 0.1788(3) 0.5345(3) 0.28066(16) 0.0316(7) Uani d . . . 1.0 . .
C C12 0.1488(3) 0.5119(3) 0.35280(17) 0.0354(7) Uani d . . . 1.0 . .
C C13 0.0819(3) 0.4244(3) 0.38175(18) 0.0413(8) Uani d . . . 1.0 . .
H H13 0.0607 0.4105 0.4302 0.05 Uiso calc U . R 1.0 . .
C C14 0.0461(3) 0.3576(3) 0.34113(19) 0.0437(9) Uani d . . . 1.0 . .
H H14 -0.0014 0.2998 0.3613 0.052 Uiso calc U . R 1.0 . .
C C15 0.0796(3) 0.3751(3) 0.27086(19) 0.0415(8) Uani d . . . 1.0 . .
H H15 0.0571 0.3275 0.2432 0.05 Uiso calc U . R 1.0 . .
C C16 0.1463(3) 0.4620(3) 0.24019(17) 0.0353(7) Uani d . . . 1.0 . .
C C21 0.1867(3) 0.5770(3) 0.40154(16) 0.0351(7) Uani d . . . 1.0 . .
C C22 0.1025(3) 0.6579(3) 0.43067(17) 0.0377(8) Uani d . . . 1.0 . .
C C23 0.1387(3) 0.7188(3) 0.47478(18) 0.0432(9) Uani d . . . 1.0 . .
H H23 0.0808 0.7734 0.494 0.052 Uiso calc U . R 1.0 . .
C C24 0.2564(3) 0.7028(3) 0.49164(17) 0.0436(9) Uani d . . . 1.0 . .
C C25 0.3395(3) 0.6218(3) 0.46337(18) 0.0418(8) Uani d . . . 1.0 . .
H H25 0.4206 0.6095 0.4748 0.05 Uiso calc U . R 1.0 . .
C C26 0.3075(3) 0.5582(3) 0.41895(17) 0.0367(8) Uani d . . . 1.0 . .
C C27 -0.0270(3) 0.6798(4) 0.4137(2) 0.0531(10) Uani d . . . 1.0 . .
H H27A -0.0683 0.6178 0.4403 0.08 Uiso calc U . R 1.0 . .
H H27B -0.0305 0.6827 0.3642 0.08 Uiso calc U . R 1.0 . .
H H27C -0.0664 0.7531 0.4257 0.08 Uiso calc U . R 1.0 . .
C C28 0.2928(4) 0.7685(4) 0.5416(2) 0.0638(12) Uani d . . . 1.0 . .
H H28A 0.2771 0.851 0.5228 0.096 Uiso calc U . R 1.0 . .
H H28B 0.3787 0.745 0.5481 0.096 Uiso calc U . R 1.0 . .
H H28C 0.246 0.752 0.5861 0.096 Uiso calc U . R 1.0 . .
C C29 0.4010(3) 0.4695(3) 0.39151(19) 0.0459(9) Uani d . . . 1.0 . .
H H29A 0.4215 0.4965 0.3422 0.069 Uiso calc U . R 1.0 . .
H H29B 0.369 0.3972 0.3977 0.069 Uiso calc U . R 1.0 . .
H H29C 0.4734 0.457 0.4168 0.069 Uiso calc U . R 1.0 . .
C C31 0.1822(3) 0.4755(3) 0.16401(17) 0.0362(8) Uani d . . . 1.0 . .
C C32 0.0971(3) 0.5264(3) 0.11631(19) 0.0446(9) Uani d . . . 1.0 . .
C C33 0.1356(4) 0.5477(4) 0.04599(19) 0.0524(10) Uani d . . . 1.0 . .
H H33 0.0784 0.5836 0.0134 0.063 Uiso calc U . R 1.0 . .
C C34 0.2545(4) 0.5181(4) 0.0223(2) 0.0553(11) Uani d . . . 1.0 . .
C C35 0.3348(4) 0.4604(3) 0.0706(2) 0.0512(10) Uani d . . . 1.0 . .
H H35 0.4156 0.4353 0.0549 0.061 Uiso calc U . R 1.0 . .
C C36 0.3012(3) 0.4380(3) 0.14113(18) 0.0417(8) Uani d . . . 1.0 . .
C C37 -0.0324(3) 0.5635(4) 0.1387(2) 0.0551(10) Uani d . . . 1.0 . .
H H37A -0.0716 0.4957 0.1559 0.083 Uiso calc U . R 1.0 . .
H H37B -0.0732 0.6113 0.0992 0.083 Uiso calc U . R 1.0 . .
H H37C -0.037 0.6078 0.1755 0.083 Uiso calc U . R 1.0 . .
C C38 0.2950(5) 0.5478(5) -0.0538(2) 0.0755(14) Uani d . . . 1.0 . .
H H38A 0.3189 0.6242 -0.064 0.113 Uiso calc U . R 1.0 . .
H H38B 0.2286 0.5474 -0.0816 0.113 Uiso calc U . R 1.0 . .
H H38C 0.3636 0.491 -0.0651 0.113 Uiso calc U . R 1.0 . .
C C39 0.3928(4) 0.3738(4) 0.1905(2) 0.0557(10) Uani d . . . 1.0 . .
H H39A 0.4287 0.4286 0.209 0.084 Uiso calc U . R 1.0 . .
H H39B 0.4559 0.3267 0.1661 0.084 Uiso calc U . R 1.0 . .
H H39C 0.3535 0.3242 0.2287 0.084 Uiso calc U . R 1.0 . .
C C41 0.2800(3) 1.0280(3) 0.29940(17) 0.0362(8) Uani d . . . 1.0 . .
F F42 0.0839(2) 0.9818(2) 0.33067(13) 0.0620(6) Uani d . . . 1.0 . .
C C42 0.1772(4) 1.0289(3) 0.34356(19) 0.0450(9) Uani d . . . 1.0 . .
F F43 0.0592(3) 1.0730(2) 0.44338(14) 0.0863(9) Uani d . . . 1.0 . .
C C43 0.1623(4) 1.0746(4) 0.4026(2) 0.0582(11) Uani d . . . 1.0 . .
F F44 0.2371(3) 1.1718(3) 0.47665(14) 0.0928(10) Uani d . . . 1.0 . .
C C44 0.2526(5) 1.1265(4) 0.4192(2) 0.0616(12) Uani d . . . 1.0 . .
F F45 0.4447(3) 1.1778(2) 0.39303(16) 0.0835(9) Uani d . . . 1.0 . .
C C45 0.3548(4) 1.1293(3) 0.3770(2) 0.0568(11) Uani d . . . 1.0 . .
F F46 0.4720(2) 1.08593(19) 0.27921(12) 0.0566(6) Uani d . . . 1.0 . .
C C46 0.3663(3) 1.0827(3) 0.31901(19) 0.0434(9) Uani d . . . 1.0 . .
B B1 0.3086(4) 0.9679(3) 0.2306(2) 0.0364(9) Uani d . . . 1.0 . .
C C51 0.3355(13) 1.0598(15) 0.1561(10) 0.029(3) Uani d U P D 0.50(2) A 1
F F52 0.1307(16) 1.1442(19) 0.1731(9) 0.048(3) Uani d U P D 0.50(2) A 1
C C52 0.2377(12) 1.1393(12) 0.1331(7) 0.033(3) Uani d U P D 0.50(2) A 1
F F53 0.1315(13) 1.2789(14) 0.0493(8) 0.067(3) Uani d U P D 0.50(2) A 1
C C53 0.2338(13) 1.2081(11) 0.0679(6) 0.041(3) Uani d U P D 0.50(2) A 1
F F54 0.3392(15) 1.2693(11) -0.0364(6) 0.083(3) Uani d U P D 0.50(2) A 1
C C54 0.3385(15) 1.1995(11) 0.0260(6) 0.047(3) Uani d U P D 0.50(2) A 1
F F55 0.5408(14) 1.1255(17) 0.0056(9) 0.092(4) Uani d U P D 0.50(2) A 1
C C55 0.4402(13) 1.1265(10) 0.0488(6) 0.045(3) Uani d U P D 0.50(2) A 1
F F56 0.5376(17) 0.990(2) 0.1323(12) 0.066(4) Uani d U P D 0.50(2) A 1
C C56 0.4361(14) 1.0604(15) 0.1137(8) 0.040(3) Uani d U P D 0.50(2) A 1
C C51A 0.3054(15) 1.0639(18) 0.1633(10) 0.038(4) Uani d U P . 0.50(2) A 2
F F52A 0.1056(16) 1.1428(19) 0.1891(9) 0.048(3) Uani d U P . 0.50(2) A 2
C C52A 0.2013(15) 1.1377(12) 0.1430(7) 0.032(3) Uani d U P . 0.50(2) A 2
F F53A 0.0887(14) 1.2771(15) 0.0644(9) 0.078(4) Uani d U P . 0.50(2) A 2
C C53A 0.1917(14) 1.2102(11) 0.0805(7) 0.043(3) Uani d U P . 0.50(2) A 2
F F54A 0.2789(15) 1.2753(12) -0.0328(7) 0.084(3) Uani d U P . 0.50(2) A 2
C C54A 0.2886(15) 1.2094(11) 0.0318(7) 0.046(3) Uani d U P . 0.50(2) A 2
F F55A 0.4916(14) 1.1364(16) -0.0011(8) 0.083(3) Uani d U P . 0.50(2) A 2
C C55A 0.3943(15) 1.1425(13) 0.0449(7) 0.050(3) Uani d U P . 0.50(2) A 2
F F56A 0.5109(16) 0.996(2) 0.1206(11) 0.060(3) Uani d U P . 0.50(2) A 2
C C56A 0.4009(14) 1.0682(15) 0.1092(9) 0.042(3) Uani d U P . 0.50(2) A 2
C C5 0.4336(3) 0.8829(3) 0.24780(17) 0.0373(8) Uani d . . . 1.0 . .
N N1 0.5068(3) 0.8105(2) 0.27020(14) 0.0367(6) Uani d . . . 1.0 . .
C C61 0.5892(3) 0.7228(3) 0.30479(18) 0.0388(8) Uani d . . . 1.0 . .
C C62 0.6470(3) 0.6370(3) 0.2692(2) 0.0471(9) Uani d . . . 1.0 . .
C C63 0.7264(3) 0.5499(3) 0.3067(2) 0.0545(11) Uani d . . . 1.0 . .
H H63 0.7696 0.4898 0.285 0.065 Uiso calc U . R 1.0 . .
C C64 0.7426(3) 0.5501(4) 0.3743(2) 0.0582(11) Uani d . . . 1.0 . .
H H64 0.7957 0.4893 0.399 0.07 Uiso calc U . R 1.0 . .
C C65 0.6835(3) 0.6366(4) 0.4071(2) 0.0548(10) Uani d . . . 1.0 . .
H H65 0.6964 0.6347 0.454 0.066 Uiso calc U . R 1.0 . .
C C66 0.6056(3) 0.7261(3) 0.37280(18) 0.0423(8) Uani d . . . 1.0 . .
C C67 0.6263(4) 0.6396(4) 0.1952(2) 0.0618(11) Uani d . . . 1.0 . .
H H67A 0.5424 0.6316 0.1922 0.093 Uiso calc U . R 1.0 . .
H H67B 0.68 0.5762 0.1784 0.093 Uiso calc U . R 1.0 . .
H H67C 0.6428 0.7128 0.1669 0.093 Uiso calc U . R 1.0 . .
C C68 0.5435(4) 0.8236(4) 0.4063(2) 0.0534(10) Uani d . . . 1.0 . .
H H68A 0.5595 0.8072 0.4552 0.08 Uiso calc U . R 1.0 . .
H H68B 0.4567 0.8331 0.4023 0.08 Uiso calc U . R 1.0 . .
H H68C 0.5738 0.8943 0.3832 0.08 Uiso calc U . R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C11 . 1.850(3) ?
P1 C4 . 1.855(3) ?
P1 C1 . 1.861(3) ?
C1 C2 . 1.561(4) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.548(5) ?
C2 B1 . 1.631(5) ?
C2 H2 . 1.0 ?
C4 C3 . 1.528(5) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C11 C12 . 1.413(4) ?
C11 C16 . 1.415(4) ?
C12 C13 . 1.397(5) ?
C12 C21 . 1.499(5) ?
C13 C14 . 1.381(5) ?
C13 H13 . 0.95 ?
C14 C15 . 1.385(5) ?
C14 H14 . 0.95 ?
C15 C16 . 1.396(5) ?
C15 H15 . 0.95 ?
C16 C31 . 1.502(5) ?
C21 C22 . 1.405(5) ?
C21 C26 . 1.416(5) ?
C22 C23 . 1.384(5) ?
C22 C27 . 1.507(5) ?
C23 C24 . 1.380(5) ?
C23 H23 . 0.95 ?
C24 C25 . 1.391(5) ?
C24 C28 . 1.515(5) ?
C25 C26 . 1.390(5) ?
C25 H25 . 0.95 ?
C26 C29 . 1.508(5) ?
C27 H27A . 0.98 ?
C27 H27B . 0.98 ?
C27 H27C . 0.98 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C29 H29A . 0.98 ?
C29 H29B . 0.98 ?
C29 H29C . 0.98 ?
C31 C32 . 1.398(5) ?
C31 C36 . 1.400(5) ?
C32 C33 . 1.398(5) ?
C32 C37 . 1.502(5) ?
C33 C34 . 1.387(6) ?
C33 H33 . 0.95 ?
C34 C35 . 1.387(6) ?
C34 C38 . 1.515(6) ?
C35 C36 . 1.392(5) ?
C35 H35 . 0.95 ?
C36 C39 . 1.506(5) ?
C37 H37A . 0.98 ?
C37 H37B . 0.98 ?
C37 H37C . 0.98 ?
C38 H38A . 0.98 ?
C38 H38B . 0.98 ?
C38 H38C . 0.98 ?
C39 H39A . 0.98 ?
C39 H39B . 0.98 ?
C39 H39C . 0.98 ?
C41 C42 . 1.376(5) ?
C41 C46 . 1.397(5) ?
C41 B1 . 1.645(5) ?
F42 C42 . 1.353(4) ?
C42 C43 . 1.372(5) ?
F43 C43 . 1.344(5) ?
C43 C44 . 1.387(6) ?
F44 C44 . 1.342(4) ?
C44 C45 . 1.351(6) ?
F45 C45 . 1.353(5) ?
C45 C46 . 1.362(5) ?
F46 C46 . 1.360(4) ?
B1 C51A . 1.576(19) ?
B1 C5 . 1.620(5) ?
B1 C51 . 1.688(18) ?
C51 C56 . 1.34(2) ?
C51 C52 . 1.384(13) ?
F52 C52 . 1.371(13) ?
C52 C53 . 1.386(12) ?
F53 C53 . 1.351(13) ?
C53 C54 . 1.371(11) ?
F54 C54 . 1.348(13) ?
C54 C55 . 1.379(11) ?
F55 C55 . 1.347(13) ?
C55 C56 . 1.369(13) ?
F56 C56 . 1.342(15) ?
C51A C52A . 1.391(18) ?
C51A C56A . 1.44(2) ?
F52A C52A . 1.339(17) ?
C52A C53A . 1.366(16) ?
F53A C53A . 1.326(17) ?
C53A C54A . 1.378(15) ?
F54A C54A . 1.367(15) ?
C54A C55A . 1.340(16) ?
F55A C55A . 1.351(17) ?
C55A C56A . 1.401(18) ?
F56A C56A . 1.400(19) ?
C5 N1 . 1.147(4) ?
N1 C61 . 1.400(4) ?
C61 C66 . 1.389(5) ?
C61 C62 . 1.397(5) ?
C62 C63 . 1.401(6) ?
C62 C67 . 1.502(6) ?
C63 C64 . 1.372(6) ?
C63 H63 . 0.95 ?
C64 C65 . 1.375(6) ?
C64 H64 . 0.95 ?
C65 C66 . 1.380(5) ?
C65 H65 . 0.95 ?
C66 C68 . 1.496(5) ?
C67 H67A . 0.98 ?
C67 H67B . 0.98 ?
C67 H67C . 0.98 ?
C68 H68A . 0.98 ?
C68 H68B . 0.98 ?
C68 H68C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 P1 C4 . . 108.00(15) ?
C11 P1 C1 . . 106.20(15) ?
C4 P1 C1 . . 89.55(16) ?
C2 C1 P1 . . 106.7(2) ?
C2 C1 H1A . . 110.4 ?
P1 C1 H1A . . 110.4 ?
C2 C1 H1B . . 110.4 ?
P1 C1 H1B . . 110.4 ?
H1A C1 H1B . . 108.6 ?
C3 C2 C1 . . 108.2(3) ?
C3 C2 B1 . . 110.6(3) ?
C1 C2 B1 . . 116.3(3) ?
C3 C2 H2 . . 107.1 ?
C1 C2 H2 . . 107.1 ?
B1 C2 H2 . . 107.1 ?
C3 C4 P1 . . 100.7(2) ?
C3 C4 H4A . . 111.6 ?
P1 C4 H4A . . 111.6 ?
C3 C4 H4B . . 111.6 ?
P1 C4 H4B . . 111.6 ?
H4A C4 H4B . . 109.4 ?
C4 C3 C2 . . 109.1(3) ?
C4 C3 H3A . . 109.9 ?
C2 C3 H3A . . 109.9 ?
C4 C3 H3B . . 109.9 ?
C2 C3 H3B . . 109.9 ?
H3A C3 H3B . . 108.3 ?
C12 C11 C16 . . 118.4(3) ?
C12 C11 P1 . . 120.1(2) ?
C16 C11 P1 . . 121.1(2) ?
C13 C12 C11 . . 119.9(3) ?
C13 C12 C21 . . 117.0(3) ?
C11 C12 C21 . . 123.1(3) ?
C14 C13 C12 . . 121.0(3) ?
C14 C13 H13 . . 119.5 ?
C12 C13 H13 . . 119.5 ?
C13 C14 C15 . . 119.7(3) ?
C13 C14 H14 . . 120.1 ?
C15 C14 H14 . . 120.1 ?
C14 C15 C16 . . 120.7(3) ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
C15 C16 C11 . . 120.1(3) ?
C15 C16 C31 . . 118.3(3) ?
C11 C16 C31 . . 121.6(3) ?
C22 C21 C26 . . 118.9(3) ?
C22 C21 C12 . . 120.3(3) ?
C26 C21 C12 . . 120.8(3) ?
C23 C22 C21 . . 119.9(3) ?
C23 C22 C27 . . 119.6(3) ?
C21 C22 C27 . . 120.5(3) ?
C24 C23 C22 . . 122.0(3) ?
C24 C23 H23 . . 119.0 ?
C22 C23 H23 . . 119.0 ?
C23 C24 C25 . . 118.1(3) ?
C23 C24 C28 . . 120.8(4) ?
C25 C24 C28 . . 121.1(4) ?
C26 C25 C24 . . 122.1(3) ?
C26 C25 H25 . . 118.9 ?
C24 C25 H25 . . 118.9 ?
C25 C26 C21 . . 119.0(3) ?
C25 C26 C29 . . 119.6(3) ?
C21 C26 C29 . . 121.4(3) ?
C22 C27 H27A . . 109.5 ?
C22 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C22 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C24 C28 H28A . . 109.5 ?
C24 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C24 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C26 C29 H29A . . 109.5 ?
C26 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
C26 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
C32 C31 C36 . . 120.3(3) ?
C32 C31 C16 . . 119.9(3) ?
C36 C31 C16 . . 119.7(3) ?
C33 C32 C31 . . 118.7(4) ?
C33 C32 C37 . . 119.3(4) ?
C31 C32 C37 . . 122.0(3) ?
C34 C33 C32 . . 122.0(4) ?
C34 C33 H33 . . 119.0 ?
C32 C33 H33 . . 119.0 ?
C33 C34 C35 . . 117.8(4) ?
C33 C34 C38 . . 120.9(4) ?
C35 C34 C38 . . 121.3(4) ?
C34 C35 C36 . . 122.3(4) ?
C34 C35 H35 . . 118.9 ?
C36 C35 H35 . . 118.9 ?
C35 C36 C31 . . 118.7(3) ?
C35 C36 C39 . . 119.4(3) ?
C31 C36 C39 . . 121.9(3) ?
C32 C37 H37A . . 109.5 ?
C32 C37 H37B . . 109.5 ?
H37A C37 H37B . . 109.5 ?
C32 C37 H37C . . 109.5 ?
H37A C37 H37C . . 109.5 ?
H37B C37 H37C . . 109.5 ?
C34 C38 H38A . . 109.5 ?
C34 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C34 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C36 C39 H39A . . 109.5 ?
C36 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C36 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
C42 C41 C46 . . 113.2(3) ?
C42 C41 B1 . . 126.7(3) ?
C46 C41 B1 . . 120.0(3) ?
F42 C42 C43 . . 115.9(4) ?
F42 C42 C41 . . 120.4(3) ?
C43 C42 C41 . . 123.7(4) ?
F43 C43 C42 . . 120.6(4) ?
F43 C43 C44 . . 119.5(4) ?
C42 C43 C44 . . 119.8(4) ?
F44 C44 C45 . . 121.6(4) ?
F44 C44 C43 . . 119.5(4) ?
C45 C44 C43 . . 118.9(4) ?
C44 C45 F45 . . 119.7(4) ?
C44 C45 C46 . . 119.5(4) ?
F45 C45 C46 . . 120.8(4) ?
F46 C46 C45 . . 117.0(3) ?
F46 C46 C41 . . 118.1(3) ?
C45 C46 C41 . . 124.8(4) ?
C51A B1 C5 . . 119.3(7) ?
C51A B1 C2 . . 106.1(8) ?
C5 B1 C2 . . 102.5(3) ?
C51A B1 C41 . . 109.6(9) ?
C5 B1 C41 . . 101.5(3) ?
C2 B1 C41 . . 118.3(3) ?
C5 B1 C51 . . 107.5(5) ?
C2 B1 C51 . . 110.9(7) ?
C41 B1 C51 . . 114.3(7) ?
C56 C51 C52 . . 115.6(14) ?
C56 C51 B1 . . 128.6(10) ?
C52 C51 B1 . . 115.6(11) ?
F52 C52 C51 . . 119.5(13) ?
F52 C52 C53 . . 115.2(11) ?
C51 C52 C53 . . 124.8(12) ?
F53 C53 C54 . . 124.1(11) ?
F53 C53 C52 . . 120.1(11) ?
C54 C53 C52 . . 115.8(9) ?
F54 C54 C53 . . 117.1(11) ?
F54 C54 C55 . . 121.8(10) ?
C53 C54 C55 . . 121.0(9) ?
F55 C55 C56 . . 122.9(12) ?
F55 C55 C54 . . 117.6(10) ?
C56 C55 C54 . . 119.6(10) ?
C51 C56 F56 . . 120.5(15) ?
C51 C56 C55 . . 122.8(13) ?
F56 C56 C55 . . 116.5(16) ?
C52A C51A C56A . . 111.9(15) ?
C52A C51A B1 . . 123.3(12) ?
C56A C51A B1 . . 123.4(13) ?
F52A C52A C53A . . 117.4(14) ?
F52A C52A C51A . . 118.0(15) ?
C53A C52A C51A . . 124.6(14) ?
F53A C53A C52A . . 121.1(12) ?
F53A C53A C54A . . 119.3(11) ?
C52A C53A C54A . . 119.4(11) ?
C55A C54A F54A . . 117.4(12) ?
C55A C54A C53A . . 121.9(11) ?
F54A C54A C53A . . 120.7(11) ?
C54A C55A F55A . . 124.6(13) ?
C54A C55A C56A . . 117.2(11) ?
F55A C55A C56A . . 118.1(13) ?
F56A C56A C55A . . 116.1(15) ?
F56A C56A C51A . . 119.1(15) ?
C55A C56A C51A . . 124.8(14) ?
N1 C5 B1 . . 165.7(3) ?
C5 N1 C61 . . 173.6(3) ?
C66 C61 C62 . . 124.7(3) ?
C66 C61 N1 . . 117.4(3) ?
C62 C61 N1 . . 117.9(3) ?
C61 C62 C63 . . 115.6(4) ?
C61 C62 C67 . . 121.9(4) ?
C63 C62 C67 . . 122.6(4) ?
C64 C63 C62 . . 120.9(4) ?
C64 C63 H63 . . 119.6 ?
C62 C63 H63 . . 119.6 ?
C63 C64 C65 . . 121.3(4) ?
C63 C64 H64 . . 119.3 ?
C65 C64 H64 . . 119.3 ?
C64 C65 C66 . . 120.8(4) ?
C64 C65 H65 . . 119.6 ?
C66 C65 H65 . . 119.6 ?
C65 C66 C61 . . 116.7(4) ?
C65 C66 C68 . . 122.0(4) ?
C61 C66 C68 . . 121.3(3) ?
C62 C67 H67A . . 109.5 ?
C62 C67 H67B . . 109.5 ?
H67A C67 H67B . . 109.5 ?
C62 C67 H67C . . 109.5 ?
H67A C67 H67C . . 109.5 ?
H67B C67 H67C . . 109.5 ?
C66 C68 H68A . . 109.5 ?
C66 C68 H68B . . 109.5 ?
H68A C68 H68B . . 109.5 ?
C66 C68 H68C . . 109.5 ?
H68A C68 H68C . . 109.5 ?
H68B C68 H68C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 P1 C1 C2 . . . . -141.3(2) ?
C4 P1 C1 C2 . . . . -32.7(2) ?
P1 C1 C2 C3 . . . . 9.4(3) ?
P1 C1 C2 B1 . . . . -115.7(3) ?
C11 P1 C4 C3 . . . . 152.9(2) ?
C1 P1 C4 C3 . . . . 46.0(3) ?
P1 C4 C3 C2 . . . . -48.3(3) ?
C1 C2 C3 C4 . . . . 25.6(4) ?
B1 C2 C3 C4 . . . . 154.0(3) ?
C4 P1 C11 C12 . . . . -143.7(3) ?
C1 P1 C11 C12 . . . . -48.7(3) ?
C4 P1 C11 C16 . . . . 44.2(3) ?
C1 P1 C11 C16 . . . . 139.2(3) ?
C16 C11 C12 C13 . . . . -3.9(5) ?
P1 C11 C12 C13 . . . . -176.2(3) ?
C16 C11 C12 C21 . . . . 175.2(3) ?
P1 C11 C12 C21 . . . . 2.9(4) ?
C11 C12 C13 C14 . . . . 1.1(5) ?
C21 C12 C13 C14 . . . . -178.0(3) ?
C12 C13 C14 C15 . . . . 1.9(5) ?
C13 C14 C15 C16 . . . . -2.0(5) ?
C14 C15 C16 C11 . . . . -0.9(5) ?
C14 C15 C16 C31 . . . . 178.8(3) ?
C12 C11 C16 C15 . . . . 3.8(5) ?
P1 C11 C16 C15 . . . . 176.1(3) ?
C12 C11 C16 C31 . . . . -175.9(3) ?
P1 C11 C16 C31 . . . . -3.7(4) ?
C13 C12 C21 C22 . . . . -74.6(4) ?
C11 C12 C21 C22 . . . . 106.3(4) ?
C13 C12 C21 C26 . . . . 105.5(4) ?
C11 C12 C21 C26 . . . . -73.7(4) ?
C26 C21 C22 C23 . . . . 1.0(5) ?
C12 C21 C22 C23 . . . . -179.0(3) ?
C26 C21 C22 C27 . . . . -179.7(3) ?
C12 C21 C22 C27 . . . . 0.4(5) ?
C21 C22 C23 C24 . . . . -0.1(5) ?
C27 C22 C23 C24 . . . . -179.5(3) ?
C22 C23 C24 C25 . . . . -0.6(5) ?
C22 C23 C24 C28 . . . . -178.4(4) ?
C23 C24 C25 C26 . . . . 0.4(5) ?
C28 C24 C25 C26 . . . . 178.2(3) ?
C24 C25 C26 C21 . . . . 0.4(5) ?
C24 C25 C26 C29 . . . . -178.4(3) ?
C22 C21 C26 C25 . . . . -1.1(5) ?
C12 C21 C26 C25 . . . . 178.9(3) ?
C22 C21 C26 C29 . . . . 177.7(3) ?
C12 C21 C26 C29 . . . . -2.4(5) ?
C15 C16 C31 C32 . . . . 76.1(4) ?
C11 C16 C31 C32 . . . . -104.2(4) ?
C15 C16 C31 C36 . . . . -104.6(4) ?
C11 C16 C31 C36 . . . . 75.1(4) ?
C36 C31 C32 C33 . . . . -5.3(5) ?
C16 C31 C32 C33 . . . . 174.0(3) ?
C36 C31 C32 C37 . . . . 177.5(3) ?
C16 C31 C32 C37 . . . . -3.1(5) ?
C31 C32 C33 C34 . . . . 1.2(6) ?
C37 C32 C33 C34 . . . . 178.4(4) ?
C32 C33 C34 C35 . . . . 3.3(6) ?
C32 C33 C34 C38 . . . . -176.8(4) ?
C33 C34 C35 C36 . . . . -3.8(6) ?
C38 C34 C35 C36 . . . . 176.3(4) ?
C34 C35 C36 C31 . . . . -0.2(6) ?
C34 C35 C36 C39 . . . . 179.4(4) ?
C32 C31 C36 C35 . . . . 4.9(5) ?
C16 C31 C36 C35 . . . . -174.4(3) ?
C32 C31 C36 C39 . . . . -174.7(3) ?
C16 C31 C36 C39 . . . . 6.0(5) ?
C46 C41 C42 F42 . . . . 178.3(3) ?
B1 C41 C42 F42 . . . . -3.4(5) ?
C46 C41 C42 C43 . . . . -2.6(5) ?
B1 C41 C42 C43 . . . . 175.7(3) ?
F42 C42 C43 F43 . . . . -1.1(5) ?
C41 C42 C43 F43 . . . . 179.8(3) ?
F42 C42 C43 C44 . . . . -178.8(3) ?
C41 C42 C43 C44 . . . . 2.0(6) ?
F43 C43 C44 F44 . . . . 1.7(6) ?
C42 C43 C44 F44 . . . . 179.5(4) ?
F43 C43 C44 C45 . . . . -178.8(4) ?
C42 C43 C44 C45 . . . . -1.0(6) ?
F44 C44 C45 F45 . . . . 0.7(6) ?
C43 C44 C45 F45 . . . . -178.8(4) ?
F44 C44 C45 C46 . . . . -179.7(4) ?
C43 C44 C45 C46 . . . . 0.8(6) ?
C44 C45 C46 F46 . . . . -178.7(4) ?
F45 C45 C46 F46 . . . . 0.9(5) ?
C44 C45 C46 C41 . . . . -1.6(6) ?
F45 C45 C46 C41 . . . . 178.0(3) ?
C42 C41 C46 F46 . . . . 179.5(3) ?
B1 C41 C46 F46 . . . . 1.0(5) ?
C42 C41 C46 C45 . . . . 2.4(5) ?
B1 C41 C46 C45 . . . . -176.1(3) ?
C3 C2 B1 C51A . . . . 54.9(8) ?
C1 C2 B1 C51A . . . . 178.8(8) ?
C3 C2 B1 C5 . . . . -71.0(3) ?
C1 C2 B1 C5 . . . . 52.9(4) ?
C3 C2 B1 C41 . . . . 178.4(3) ?
C1 C2 B1 C41 . . . . -57.7(4) ?
C3 C2 B1 C51 . . . . 43.5(7) ?
C1 C2 B1 C51 . . . . 167.4(6) ?
C42 C41 B1 C51A . . . . 109.2(8) ?
C46 C41 B1 C51A . . . . -72.6(8) ?
C42 C41 B1 C5 . . . . -123.7(4) ?
C46 C41 B1 C5 . . . . 54.5(4) ?
C42 C41 B1 C2 . . . . -12.5(5) ?
C46 C41 B1 C2 . . . . 165.7(3) ?
C42 C41 B1 C51 . . . . 120.9(6) ?
C46 C41 B1 C51 . . . . -60.9(7) ?
C5 B1 C51 C56 . . . . 5.(2) ?
C2 B1 C51 C56 . . . . -105.8(19) ?
C41 B1 C51 C56 . . . . 117.3(19) ?
C5 B1 C51 C52 . . . . 179.8(13) ?
C2 B1 C51 C52 . . . . 68.4(16) ?
C41 B1 C51 C52 . . . . -68.4(16) ?
C56 C51 C52 F52 . . . . 179.6(19) ?
B1 C51 C52 F52 . . . . 5.(3) ?
C56 C51 C52 C53 . . . . 7.(3) ?
B1 C51 C52 C53 . . . . -167.7(14) ?
F52 C52 C53 F53 . . . . 4.(2) ?
C51 C52 C53 F53 . . . . 176.7(17) ?
F52 C52 C53 C54 . . . . -176.7(17) ?
C51 C52 C53 C54 . . . . -4.(2) ?
F53 C53 C54 F54 . . . . 2.(2) ?
C52 C53 C54 F54 . . . . -176.9(14) ?
F53 C53 C54 C55 . . . . 179.0(15) ?
C52 C53 C54 C55 . . . . 0.(2) ?
F54 C54 C55 F55 . . . . -1.(2) ?
C53 C54 C55 F55 . . . . -177.8(15) ?
F54 C54 C55 C56 . . . . 177.5(15) ?
C53 C54 C55 C56 . . . . 1.(2) ?
C52 C51 C56 F56 . . . . 177.(2) ?
B1 C51 C56 F56 . . . . -8.(3) ?
C52 C51 C56 C55 . . . . -6.(3) ?
B1 C51 C56 C55 . . . . 167.9(15) ?
F55 C55 C56 C51 . . . . -178.7(19) ?
C54 C55 C56 C51 . . . . 3.(3) ?
F55 C55 C56 F56 . . . . -2.(3) ?
C54 C55 C56 F56 . . . . 179.1(18) ?
C5 B1 C51A C52A . . . . 177.4(15) ?
C2 B1 C51A C52A . . . . 63.(2) ?
C41 B1 C51A C52A . . . . -66.(2) ?
C5 B1 C51A C56A . . . . 12.(2) ?
C2 B1 C51A C56A . . . . -103.1(18) ?
C41 B1 C51A C56A . . . . 128.1(18) ?
C56A C51A C52A F52A . . . . -179.3(19) ?
B1 C51A C52A F52A . . . . 14.(3) ?
C56A C51A C52A C53A . . . . -3.(3) ?
B1 C51A C52A C53A . . . . -170.1(15) ?
F52A C52A C53A F53A . . . . -5.(3) ?
C51A C52A C53A F53A . . . . 179.1(19) ?
F52A C52A C53A C54A . . . . 178.9(17) ?
C51A C52A C53A C54A . . . . 3.(3) ?
F53A C53A C54A C55A . . . . -179.2(15) ?
C52A C53A C54A C55A . . . . -3.(2) ?
F53A C53A C54A F54A . . . . -1.(2) ?
C52A C53A C54A F54A . . . . 175.6(14) ?
F54A C54A C55A F55A . . . . 0.(2) ?
C53A C54A C55A F55A . . . . 178.7(15) ?
F54A C54A C55A C56A . . . . -175.0(14) ?
C53A C54A C55A C56A . . . . 3.(2) ?
C54A C55A C56A F56A . . . . 177.7(17) ?
F55A C55A C56A F56A . . . . 2.(2) ?
C54A C55A C56A C51A . . . . -4.(3) ?
F55A C55A C56A C51A . . . . -179.8(18) ?
C52A C51A C56A F56A . . . . -178.1(19) ?
B1 C51A C56A F56A . . . . -11.(3) ?
C52A C51A C56A C55A . . . . 4.(3) ?
B1 C51A C56A C55A . . . . 170.9(15) ?
C51A B1 C5 N1 . . . . -169.5(16) ?
C2 B1 C5 N1 . . . . -52.7(14) ?
C41 B1 C5 N1 . . . . 70.0(14) ?
C51 B1 C5 N1 . . . . -169.7(15) ?
C66 C61 C62 C63 . . . . -0.1(5) ?
N1 C61 C62 C63 . . . . -178.6(3) ?
C66 C61 C62 C67 . . . . -179.2(4) ?
N1 C61 C62 C67 . . . . 2.4(5) ?
C61 C62 C63 C64 . . . . 1.2(5) ?
C67 C62 C63 C64 . . . . -179.7(4) ?
C62 C63 C64 C65 . . . . -1.3(6) ?
C63 C64 C65 C66 . . . . 0.1(6) ?
C64 C65 C66 C61 . . . . 1.0(5) ?
C64 C65 C66 C68 . . . . -177.7(4) ?
C62 C61 C66 C65 . . . . -1.0(5) ?
N1 C61 C66 C65 . . . . 177.5(3) ?
C62 C61 C66 C68 . . . . 177.7(3) ?
N1 C61 C66 C68 . . . . -3.8(5) ?



####################################################################### 
# 
# 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_erk9525
_database_code_depnum_ccdc_archive 'CCDC 1953118'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-09-12 deposited with the CCDC.	2020-06-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H46 B F10 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         818.60

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6994(2)
_cell_length_b                   23.0965(6)
_cell_length_c                   20.3461(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.2480(10)
_cell_angle_gamma                90
_cell_volume                     4076.82(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      2.6360
_cell_measurement_theta_max      27.4285
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1704

_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            69520
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_refine_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.

One pentane molecule is disordered over two positions. Several 
restraints (SADI, SAME, ISOR and SIMU) were used in order to improve
refinement stability.

The hydrogen at B1 and P1 atoms were refined freely.
;

_reflns_number_total             9331
_reflns_number_gt                7586
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1299
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.078
_refine_ls_number_reflns         9331
_refine_ls_number_parameters     574
_refine_ls_number_restraints     127
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+3.2946P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.322
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.53172(5) 0.70683(2) 0.40445(2) 0.01692(11) Uani d . . . 1.0 . .
H H01 0.622(3) 0.6685(10) 0.3829(11) 0.027(6) Uiso d . . . 1.0 . .
B B1 0.6744(2) 0.75483(10) 0.27366(11) 0.0211(4) Uani d . . . 1.0 . .
H H02 0.737(2) 0.7231(9) 0.3090(10) 0.018(5) Uiso d . . . 1.0 . .
C C1 0.4224(2) 0.73723(9) 0.33353(9) 0.0217(4) Uani d . . . 1.0 . .
H H1A 0.4009 0.7079 0.2986 0.026 Uiso calc U . R 1.0 . .
H H1B 0.324 0.7543 0.3457 0.026 Uiso calc U . R 1.0 . .
C C2 0.5349(2) 0.78449(8) 0.31187(9) 0.0204(4) Uani d . . . 1.0 . .
H H2 0.4773 0.8123 0.2815 0.024 Uiso calc U . R 1.0 . .
C C4 0.6417(2) 0.77066(8) 0.42932(9) 0.0204(4) Uani d . . . 1.0 . .
H H4A 0.6178 0.7836 0.4738 0.024 Uiso calc U . R 1.0 . .
H H4B 0.7538 0.7632 0.4293 0.024 Uiso calc U . R 1.0 . .
C C3 0.5888(2) 0.81604(9) 0.37647(10) 0.0242(4) Uani d . . . 1.0 . .
H H3A 0.5031 0.8394 0.392 0.029 Uiso calc U . R 1.0 . .
H H3B 0.6751 0.8425 0.3686 0.029 Uiso calc U . R 1.0 . .
C C11 0.4337(2) 0.66896(8) 0.46708(9) 0.0179(4) Uani d . . . 1.0 . .
C C12 0.3116(2) 0.69454(8) 0.49834(9) 0.0193(4) Uani d . . . 1.0 . .
C C13 0.2424(2) 0.66342(9) 0.54664(9) 0.0241(4) Uani d . . . 1.0 . .
H H13 0.1608 0.6805 0.5684 0.029 Uiso calc U . R 1.0 . .
C C14 0.2904(2) 0.60791(9) 0.56349(10) 0.0258(4) Uani d . . . 1.0 . .
H H14 0.2412 0.5871 0.5963 0.031 Uiso calc U . R 1.0 . .
C C15 0.4104(2) 0.58264(9) 0.53259(10) 0.0234(4) Uani d . . . 1.0 . .
H H15 0.4422 0.5444 0.5443 0.028 Uiso calc U . R 1.0 . .
C C16 0.4849(2) 0.61251(8) 0.48464(9) 0.0192(4) Uani d . . . 1.0 . .
C C21 0.2516(2) 0.75364(8) 0.47996(9) 0.0193(4) Uani d . . . 1.0 . .
C C22 0.3113(2) 0.80314(9) 0.51245(9) 0.0234(4) Uani d . . . 1.0 . .
C C23 0.2539(2) 0.85721(9) 0.49209(10) 0.0279(4) Uani d . . . 1.0 . .
H H23 0.2954 0.891 0.5132 0.033 Uiso calc U . R 1.0 . .
C C24 0.1379(2) 0.86305(9) 0.44192(11) 0.0291(5) Uani d . . . 1.0 . .
C C25 0.0752(2) 0.81300(9) 0.41244(10) 0.0268(4) Uani d . . . 1.0 . .
H H25 -0.0061 0.8164 0.3788 0.032 Uiso calc U . R 1.0 . .
C C26 0.1286(2) 0.75844(9) 0.43098(9) 0.0227(4) Uani d . . . 1.0 . .
C C27 0.4288(3) 0.79940(10) 0.57074(10) 0.0303(5) Uani d . . . 1.0 . .
H H27A 0.5031 0.8311 0.5686 0.045 Uiso calc U . R 1.0 . .
H H27B 0.483 0.7623 0.5698 0.045 Uiso calc U . R 1.0 . .
H H27C 0.3765 0.8024 0.6116 0.045 Uiso calc U . R 1.0 . .
C C28 0.0788(3) 0.92204(11) 0.41995(14) 0.0442(6) Uani d . . . 1.0 . .
H H28A 0.0982 0.9498 0.456 0.066 Uiso calc U . R 1.0 . .
H H28B -0.0322 0.9198 0.4079 0.066 Uiso calc U . R 1.0 . .
H H28C 0.1321 0.9347 0.3817 0.066 Uiso calc U . R 1.0 . .
C C29 0.0565(2) 0.70471(9) 0.39956(10) 0.0264(4) Uani d . . . 1.0 . .
H H29A -0.0196 0.7159 0.3639 0.04 Uiso calc U . R 1.0 . .
H H29B 0.0055 0.6825 0.4328 0.04 Uiso calc U . R 1.0 . .
H H29C 0.1367 0.6809 0.3817 0.04 Uiso calc U . R 1.0 . .
C C31 0.6213(2) 0.58505(8) 0.45615(9) 0.0191(4) Uani d . . . 1.0 . .
C C32 0.7650(2) 0.58744(9) 0.49232(10) 0.0261(4) Uani d . . . 1.0 . .
C C33 0.8929(2) 0.56401(9) 0.46471(12) 0.0313(5) Uani d . . . 1.0 . .
H H33 0.99 0.565 0.4893 0.038 Uiso calc U . R 1.0 . .
C C34 0.8828(2) 0.53929(9) 0.40264(11) 0.0290(5) Uani d . . . 1.0 . .
C C35 0.7391(2) 0.53662(9) 0.36784(11) 0.0260(4) Uani d . . . 1.0 . .
H H35 0.7305 0.5193 0.3254 0.031 Uiso calc U . R 1.0 . .
C C36 0.6074(2) 0.55870(8) 0.39381(10) 0.0211(4) Uani d . . . 1.0 . .
C C37 0.7816(3) 0.61525(11) 0.55958(12) 0.0413(6) Uani d . . . 1.0 . .
H H37A 0.7378 0.6544 0.557 0.062 Uiso calc U . R 1.0 . .
H H37B 0.891 0.6175 0.5748 0.062 Uiso calc U . R 1.0 . .
H H37C 0.7267 0.592 0.5907 0.062 Uiso calc U . R 1.0 . .
C C38 1.0245(3) 0.51710(12) 0.37203(15) 0.0471(7) Uani d . . . 1.0 . .
H H38A 1.0611 0.5465 0.3421 0.071 Uiso calc U . R 1.0 . .
H H38B 0.9987 0.4816 0.3473 0.071 Uiso calc U . R 1.0 . .
H H38C 1.1055 0.5088 0.4068 0.071 Uiso calc U . R 1.0 . .
C C39 0.4536(2) 0.55461(10) 0.35475(11) 0.0301(5) Uani d . . . 1.0 . .
H H39A 0.4687 0.5403 0.3103 0.045 Uiso calc U . R 1.0 . .
H H39B 0.4056 0.593 0.3517 0.045 Uiso calc U . R 1.0 . .
H H39C 0.3866 0.5279 0.3768 0.045 Uiso calc U . R 1.0 . .
C C41 0.8087(2) 0.79913(9) 0.25123(9) 0.0245(4) Uani d . . . 1.0 . .
C C42 0.8069(2) 0.85889(10) 0.25037(11) 0.0324(5) Uani d . . . 1.0 . .
F F42 0.67613(16) 0.88842(6) 0.26077(7) 0.0406(3) Uani d . . . 1.0 . .
C C43 0.9343(3) 0.89301(12) 0.24051(12) 0.0442(6) Uani d . . . 1.0 . .
F F43 0.9264(2) 0.95091(7) 0.24478(9) 0.0662(5) Uani d . . . 1.0 . .
C C44 1.0710(3) 0.86704(15) 0.22644(12) 0.0494(8) Uani d . . . 1.0 . .
F F44 1.19542(19) 0.89939(10) 0.21710(9) 0.0752(6) Uani d U . . 1.0 . .
C C45 1.0772(2) 0.80787(14) 0.22279(11) 0.0433(7) Uani d . . . 1.0 . .
F F45 1.20828(15) 0.78131(9) 0.20764(8) 0.0630(5) Uani d U . . 1.0 . .
C C46 0.9487(2) 0.77570(11) 0.23566(10) 0.0303(5) Uani d . . . 1.0 . .
F F46 0.96569(14) 0.71748(6) 0.23344(6) 0.0374(3) Uani d . . . 1.0 . .
C C51 0.6033(2) 0.71713(9) 0.21028(10) 0.0240(4) Uani d . . . 1.0 . .
C C52 0.5201(2) 0.74348(10) 0.15767(10) 0.0263(4) Uani d . . . 1.0 . .
F F52 0.50299(13) 0.80180(6) 0.15740(6) 0.0297(3) Uani d . . . 1.0 . .
C C53 0.4506(2) 0.71400(12) 0.10464(10) 0.0378(6) Uani d . . . 1.0 . .
F F53 0.36964(17) 0.74246(8) 0.05552(7) 0.0548(4) Uani d . . . 1.0 . .
C C54 0.4626(3) 0.65487(13) 0.10221(12) 0.0448(7) Uani d . . . 1.0 . .
F F54 0.3915(2) 0.62498(9) 0.05183(8) 0.0688(6) Uani d . . . 1.0 . .
C C55 0.5459(3) 0.62622(11) 0.15236(13) 0.0446(6) Uani d . . . 1.0 . .
F F55 0.5583(2) 0.56812(7) 0.15109(9) 0.0692(5) Uani d . . . 1.0 . .
C C56 0.6133(3) 0.65765(10) 0.20475(11) 0.0337(5) Uani d . . . 1.0 . .
F F56 0.69113(19) 0.62647(6) 0.25299(7) 0.0487(4) Uani d . . . 1.0 . .
C C61 1.1682(9) 0.6051(3) 0.2125(4) 0.0465(14) Uani d U P D 0.709(6) A 1
H H61A 1.2666 0.6096 0.2387 0.07 Uiso calc U P R 0.709(6) A 1
H H61B 1.1626 0.633 0.1761 0.07 Uiso calc U P R 0.709(6) A 1
H H61C 1.0831 0.6122 0.2405 0.07 Uiso calc U P R 0.709(6) A 1
C C62 1.1560(5) 0.5446(2) 0.1851(2) 0.0497(11) Uani d U P D 0.709(6) A 1
H H62A 1.2433 0.5374 0.1576 0.06 Uiso calc U P R 0.709(6) A 1
H H62B 1.1638 0.5166 0.222 0.06 Uiso calc U P R 0.709(6) A 1
C C63 1.0098(9) 0.5351(3) 0.1451(4) 0.074(2) Uani d U P D 0.709(6) A 1
H H63A 1.0034 0.5638 0.1088 0.089 Uiso calc U P R 0.709(6) A 1
H H63B 0.9239 0.5433 0.1731 0.089 Uiso calc U P R 0.709(6) A 1
C C64 0.9852(6) 0.4767(2) 0.1158(3) 0.0686(15) Uani d U P D 0.709(6) A 1
H H64A 1.0739 0.467 0.09 0.082 Uiso calc U P R 0.709(6) A 1
H H64B 0.9825 0.448 0.1519 0.082 Uiso calc U P R 0.709(6) A 1
C C65 0.8417(8) 0.4716(3) 0.0726(5) 0.094(3) Uani d U P D 0.709(6) A 1
H H65A 0.8326 0.4321 0.055 0.141 Uiso calc U P R 0.709(6) A 1
H H65B 0.753 0.4801 0.098 0.141 Uiso calc U P R 0.709(6) A 1
H H65C 0.8444 0.4992 0.0361 0.141 Uiso calc U P R 0.709(6) A 1
C C61A 0.8747(18) 0.4602(7) 0.0377(6) 0.063(4) Uani d U P D 0.291(6) A 2
H H61D 0.778 0.439 0.0283 0.094 Uiso calc U P R 0.291(6) A 2
H H61E 0.8888 0.4878 0.002 0.094 Uiso calc U P R 0.291(6) A 2
H H61F 0.961 0.4329 0.041 0.094 Uiso calc U P R 0.291(6) A 2
C C62A 0.8691(13) 0.4926(5) 0.1018(5) 0.047(3) Uani d U P D 0.291(6) A 2
H H62C 0.7799 0.5193 0.0983 0.056 Uiso calc U P R 0.291(6) A 2
H H62D 0.8521 0.4645 0.1373 0.056 Uiso calc U P R 0.291(6) A 2
C C63A 1.0110(16) 0.5264(6) 0.1207(5) 0.041(3) Uani d U P D 0.291(6) A 2
H H63C 1.0289 0.5544 0.0852 0.049 Uiso calc U P R 0.291(6) A 2
H H63D 1.1003 0.4998 0.125 0.049 Uiso calc U P R 0.291(6) A 2
C C64A 1.0006(13) 0.5587(5) 0.1845(5) 0.061(3) Uani d U P D 0.291(6) A 2
H H64C 0.9213 0.5894 0.1786 0.073 Uiso calc U P R 0.291(6) A 2
H H64D 0.9697 0.5318 0.219 0.073 Uiso calc U P R 0.291(6) A 2
C C65A 1.151(2) 0.5849(8) 0.2053(12) 0.063(6) Uani d U P D 0.291(6) A 2
H H65D 1.1435 0.6059 0.2468 0.095 Uiso calc U P R 0.291(6) A 2
H H65E 1.2292 0.5544 0.2116 0.095 Uiso calc U P R 0.291(6) A 2
H H65F 1.1809 0.6119 0.1713 0.095 Uiso calc U P R 0.291(6) A 2


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C4 . 1.8093(19) ?
P1 C11 . 1.8101(19) ?
P1 C1 . 1.8101(18) ?
P1 H01 . 1.28(2) ?
B1 C51 . 1.638(3) ?
B1 C2 . 1.639(3) ?
B1 C41 . 1.643(3) ?
B1 H02 . 1.14(2) ?
C1 C2 . 1.552(3) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.545(3) ?
C2 H2 . 1.0 ?
C4 C3 . 1.547(3) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C11 C12 . 1.408(3) ?
C11 C16 . 1.415(3) ?
C12 C13 . 1.390(3) ?
C12 C21 . 1.499(3) ?
C13 C14 . 1.384(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.386(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.393(3) ?
C15 H15 . 0.95 ?
C16 C31 . 1.499(3) ?
C21 C22 . 1.401(3) ?
C21 C26 . 1.411(3) ?
C22 C23 . 1.396(3) ?
C22 C27 . 1.509(3) ?
C23 C24 . 1.388(3) ?
C23 H23 . 0.95 ?
C24 C25 . 1.395(3) ?
C24 C28 . 1.512(3) ?
C25 C26 . 1.386(3) ?
C25 H25 . 0.95 ?
C26 C29 . 1.511(3) ?
C27 H27A . 0.98 ?
C27 H27B . 0.98 ?
C27 H27C . 0.98 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C29 H29A . 0.98 ?
C29 H29B . 0.98 ?
C29 H29C . 0.98 ?
C31 C32 . 1.403(3) ?
C31 C36 . 1.404(3) ?
C32 C33 . 1.393(3) ?
C32 C37 . 1.509(3) ?
C33 C34 . 1.383(3) ?
C33 H33 . 0.95 ?
C34 C35 . 1.392(3) ?
C34 C38 . 1.511(3) ?
C35 C36 . 1.393(3) ?
C35 H35 . 0.95 ?
C36 C39 . 1.507(3) ?
C37 H37A . 0.98 ?
C37 H37B . 0.98 ?
C37 H37C . 0.98 ?
C38 H38A . 0.98 ?
C38 H38B . 0.98 ?
C38 H38C . 0.98 ?
C39 H39A . 0.98 ?
C39 H39B . 0.98 ?
C39 H39C . 0.98 ?
C41 C42 . 1.380(3) ?
C41 C46 . 1.390(3) ?
C42 F42 . 1.357(3) ?
C42 C43 . 1.387(3) ?
C43 F43 . 1.342(3) ?
C43 C44 . 1.380(4) ?
C44 F44 . 1.341(3) ?
C44 C45 . 1.370(4) ?
C45 F45 . 1.350(3) ?
C45 C46 . 1.384(3) ?
C46 F46 . 1.354(3) ?
C51 C56 . 1.382(3) ?
C51 C52 . 1.387(3) ?
C52 F52 . 1.355(3) ?
C52 C53 . 1.377(3) ?
C53 F53 . 1.350(3) ?
C53 C54 . 1.371(4) ?
C54 F54 . 1.347(3) ?
C54 C55 . 1.376(4) ?
C55 F55 . 1.347(3) ?
C55 C56 . 1.384(3) ?
C56 F56 . 1.357(3) ?
C61 C62 . 1.505(6) ?
C61 H61A . 0.98 ?
C61 H61B . 0.98 ?
C61 H61C . 0.98 ?
C62 C63 . 1.475(8) ?
C62 H62A . 0.99 ?
C62 H62B . 0.99 ?
C63 C64 . 1.484(8) ?
C63 H63A . 0.99 ?
C63 H63B . 0.99 ?
C64 C65 . 1.478(8) ?
C64 H64A . 0.99 ?
C64 H64B . 0.99 ?
C65 H65A . 0.98 ?
C65 H65B . 0.98 ?
C65 H65C . 0.98 ?
C61A C62A . 1.508(12) ?
C61A H61D . 0.98 ?
C61A H61E . 0.98 ?
C61A H61F . 0.98 ?
C62A C63A . 1.487(12) ?
C62A H62C . 0.99 ?
C62A H62D . 0.99 ?
C63A C64A . 1.506(12) ?
C63A H63C . 0.99 ?
C63A H63D . 0.99 ?
C64A C65A . 1.477(13) ?
C64A H64C . 0.99 ?
C64A H64D . 0.99 ?
C65A H65D . 0.98 ?
C65A H65E . 0.98 ?
C65A H65F . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 P1 C11 . . 117.63(9) ?
C4 P1 C1 . . 98.21(9) ?
C11 P1 C1 . . 120.10(8) ?
C4 P1 H01 . . 109.5(10) ?
C11 P1 H01 . . 103.8(10) ?
C1 P1 H01 . . 107.1(10) ?
C51 B1 C2 . . 110.26(15) ?
C51 B1 C41 . . 110.29(16) ?
C2 B1 C41 . . 115.98(17) ?
C51 B1 H02 . . 106.9(10) ?
C2 B1 H02 . . 108.0(11) ?
C41 B1 H02 . . 104.9(10) ?
C2 C1 P1 . . 101.17(12) ?
C2 C1 H1A . . 111.5 ?
P1 C1 H1A . . 111.5 ?
C2 C1 H1B . . 111.5 ?
P1 C1 H1B . . 111.5 ?
H1A C1 H1B . . 109.4 ?
C3 C2 C1 . . 104.37(15) ?
C3 C2 B1 . . 114.35(15) ?
C1 C2 B1 . . 110.21(16) ?
C3 C2 H2 . . 109.2 ?
C1 C2 H2 . . 109.2 ?
B1 C2 H2 . . 109.2 ?
C3 C4 P1 . . 103.50(12) ?
C3 C4 H4A . . 111.1 ?
P1 C4 H4A . . 111.1 ?
C3 C4 H4B . . 111.1 ?
P1 C4 H4B . . 111.1 ?
H4A C4 H4B . . 109.0 ?
C2 C3 C4 . . 109.13(15) ?
C2 C3 H3A . . 109.9 ?
C4 C3 H3A . . 109.9 ?
C2 C3 H3B . . 109.9 ?
C4 C3 H3B . . 109.9 ?
H3A C3 H3B . . 108.3 ?
C12 C11 C16 . . 120.43(17) ?
C12 C11 P1 . . 121.72(14) ?
C16 C11 P1 . . 117.84(14) ?
C13 C12 C11 . . 118.91(17) ?
C13 C12 C21 . . 119.06(17) ?
C11 C12 C21 . . 122.01(16) ?
C14 C13 C12 . . 121.02(18) ?
C14 C13 H13 . . 119.5 ?
C12 C13 H13 . . 119.5 ?
C13 C14 C15 . . 120.09(18) ?
C13 C14 H14 . . 120.0 ?
C15 C14 H14 . . 120.0 ?
C14 C15 C16 . . 120.94(18) ?
C14 C15 H15 . . 119.5 ?
C16 C15 H15 . . 119.5 ?
C15 C16 C11 . . 118.60(17) ?
C15 C16 C31 . . 118.95(17) ?
C11 C16 C31 . . 122.37(16) ?
C22 C21 C26 . . 120.29(17) ?
C22 C21 C12 . . 120.99(16) ?
C26 C21 C12 . . 118.67(17) ?
C23 C22 C21 . . 118.51(18) ?
C23 C22 C27 . . 119.41(18) ?
C21 C22 C27 . . 122.00(18) ?
C24 C23 C22 . . 122.0(2) ?
C24 C23 H23 . . 119.0 ?
C22 C23 H23 . . 119.0 ?
C23 C24 C25 . . 118.40(19) ?
C23 C24 C28 . . 121.2(2) ?
C25 C24 C28 . . 120.4(2) ?
C26 C25 C24 . . 121.61(19) ?
C26 C25 H25 . . 119.2 ?
C24 C25 H25 . . 119.2 ?
C25 C26 C21 . . 119.01(19) ?
C25 C26 C29 . . 120.75(18) ?
C21 C26 C29 . . 120.24(17) ?
C22 C27 H27A . . 109.5 ?
C22 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C22 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C24 C28 H28A . . 109.5 ?
C24 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C24 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C26 C29 H29A . . 109.5 ?
C26 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
C26 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
C32 C31 C36 . . 120.32(18) ?
C32 C31 C16 . . 118.68(17) ?
C36 C31 C16 . . 120.98(16) ?
C33 C32 C31 . . 118.70(19) ?
C33 C32 C37 . . 120.37(19) ?
C31 C32 C37 . . 120.93(19) ?
C34 C33 C32 . . 122.04(19) ?
C34 C33 H33 . . 119.0 ?
C32 C33 H33 . . 119.0 ?
C33 C34 C35 . . 118.46(19) ?
C33 C34 C38 . . 121.2(2) ?
C35 C34 C38 . . 120.3(2) ?
C34 C35 C36 . . 121.6(2) ?
C34 C35 H35 . . 119.2 ?
C36 C35 H35 . . 119.2 ?
C35 C36 C31 . . 118.86(18) ?
C35 C36 C39 . . 119.96(18) ?
C31 C36 C39 . . 121.17(17) ?
C32 C37 H37A . . 109.5 ?
C32 C37 H37B . . 109.5 ?
H37A C37 H37B . . 109.5 ?
C32 C37 H37C . . 109.5 ?
H37A C37 H37C . . 109.5 ?
H37B C37 H37C . . 109.5 ?
C34 C38 H38A . . 109.5 ?
C34 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C34 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C36 C39 H39A . . 109.5 ?
C36 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C36 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
C42 C41 C46 . . 113.3(2) ?
C42 C41 B1 . . 128.22(18) ?
C46 C41 B1 . . 118.28(19) ?
F42 C42 C41 . . 120.63(19) ?
F42 C42 C43 . . 115.2(2) ?
C41 C42 C43 . . 124.2(2) ?
F43 C43 C44 . . 119.7(2) ?
F43 C43 C42 . . 120.7(3) ?
C44 C43 C42 . . 119.5(3) ?
F44 C44 C45 . . 120.8(3) ?
F44 C44 C43 . . 120.3(3) ?
C45 C44 C43 . . 118.9(2) ?
F45 C45 C44 . . 120.2(2) ?
F45 C45 C46 . . 120.5(3) ?
C44 C45 C46 . . 119.3(2) ?
F46 C46 C45 . . 115.8(2) ?
F46 C46 C41 . . 119.60(19) ?
C45 C46 C41 . . 124.6(2) ?
C56 C51 C52 . . 113.9(2) ?
C56 C51 B1 . . 124.75(18) ?
C52 C51 B1 . . 121.25(19) ?
F52 C52 C53 . . 116.51(19) ?
F52 C52 C51 . . 119.35(18) ?
C53 C52 C51 . . 124.1(2) ?
F53 C53 C54 . . 119.7(2) ?
F53 C53 C52 . . 120.9(2) ?
C54 C53 C52 . . 119.4(2) ?
F54 C54 C53 . . 120.4(3) ?
F54 C54 C55 . . 120.3(3) ?
C53 C54 C55 . . 119.3(2) ?
F55 C55 C54 . . 120.2(2) ?
F55 C55 C56 . . 120.5(3) ?
C54 C55 C56 . . 119.2(2) ?
F56 C56 C51 . . 120.0(2) ?
F56 C56 C55 . . 116.0(2) ?
C51 C56 C55 . . 124.0(2) ?
C62 C61 H61A . . 109.5 ?
C62 C61 H61B . . 109.5 ?
H61A C61 H61B . . 109.5 ?
C62 C61 H61C . . 109.5 ?
H61A C61 H61C . . 109.5 ?
H61B C61 H61C . . 109.5 ?
C63 C62 C61 . . 112.1(5) ?
C63 C62 H62A . . 109.2 ?
C61 C62 H62A . . 109.2 ?
C63 C62 H62B . . 109.2 ?
C61 C62 H62B . . 109.2 ?
H62A C62 H62B . . 107.9 ?
C62 C63 C64 . . 116.7(6) ?
C62 C63 H63A . . 108.1 ?
C64 C63 H63A . . 108.1 ?
C62 C63 H63B . . 108.1 ?
C64 C63 H63B . . 108.1 ?
H63A C63 H63B . . 107.3 ?
C65 C64 C63 . . 113.7(6) ?
C65 C64 H64A . . 108.8 ?
C63 C64 H64A . . 108.8 ?
C65 C64 H64B . . 108.8 ?
C63 C64 H64B . . 108.8 ?
H64A C64 H64B . . 107.7 ?
C64 C65 H65A . . 109.5 ?
C64 C65 H65B . . 109.5 ?
H65A C65 H65B . . 109.5 ?
C64 C65 H65C . . 109.5 ?
H65A C65 H65C . . 109.5 ?
H65B C65 H65C . . 109.5 ?
C62A C61A H61D . . 109.5 ?
C62A C61A H61E . . 109.5 ?
H61D C61A H61E . . 109.5 ?
C62A C61A H61F . . 109.5 ?
H61D C61A H61F . . 109.5 ?
H61E C61A H61F . . 109.5 ?
C63A C62A C61A . . 113.8(10) ?
C63A C62A H62C . . 108.8 ?
C61A C62A H62C . . 108.8 ?
C63A C62A H62D . . 108.8 ?
C61A C62A H62D . . 108.8 ?
H62C C62A H62D . . 107.7 ?
C62A C63A C64A . . 112.4(11) ?
C62A C63A H63C . . 109.1 ?
C64A C63A H63C . . 109.1 ?
C62A C63A H63D . . 109.1 ?
C64A C63A H63D . . 109.1 ?
H63C C63A H63D . . 107.9 ?
C65A C64A C63A . . 110.0(13) ?
C65A C64A H64C . . 109.7 ?
C63A C64A H64C . . 109.7 ?
C65A C64A H64D . . 109.7 ?
C63A C64A H64D . . 109.7 ?
H64C C64A H64D . . 108.2 ?
C64A C65A H65D . . 109.5 ?
C64A C65A H65E . . 109.5 ?
H65D C65A H65E . . 109.5 ?
C64A C65A H65F . . 109.5 ?
H65D C65A H65F . . 109.5 ?
H65E C65A H65F . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 P1 C1 C2 . . . . 28.52(14) ?
C11 P1 C1 C2 . . . . 157.21(12) ?
P1 C1 C2 C3 . . . . -46.71(16) ?
P1 C1 C2 B1 . . . . 76.51(15) ?
C51 B1 C2 C3 . . . . 174.23(16) ?
C41 B1 C2 C3 . . . . -59.5(2) ?
C51 B1 C2 C1 . . . . 57.04(19) ?
C41 B1 C2 C1 . . . . -176.72(15) ?
C11 P1 C4 C3 . . . . -132.04(13) ?
C1 P1 C4 C3 . . . . -1.70(14) ?
C1 C2 C3 C4 . . . . 49.57(19) ?
B1 C2 C3 C4 . . . . -70.9(2) ?
P1 C4 C3 C2 . . . . -26.85(18) ?
C4 P1 C11 C12 . . . . 65.62(17) ?
C1 P1 C11 C12 . . . . -53.69(18) ?
C4 P1 C11 C16 . . . . -113.59(15) ?
C1 P1 C11 C16 . . . . 127.10(15) ?
C16 C11 C12 C13 . . . . 0.0(3) ?
P1 C11 C12 C13 . . . . -179.23(14) ?
C16 C11 C12 C21 . . . . -178.46(16) ?
P1 C11 C12 C21 . . . . 2.3(2) ?
C11 C12 C13 C14 . . . . -0.8(3) ?
C21 C12 C13 C14 . . . . 177.67(18) ?
C12 C13 C14 C15 . . . . 0.6(3) ?
C13 C14 C15 C16 . . . . 0.4(3) ?
C14 C15 C16 C11 . . . . -1.2(3) ?
C14 C15 C16 C31 . . . . 175.62(18) ?
C12 C11 C16 C15 . . . . 1.0(3) ?
P1 C11 C16 C15 . . . . -179.75(14) ?
C12 C11 C16 C31 . . . . -175.69(16) ?
P1 C11 C16 C31 . . . . 3.5(2) ?
C13 C12 C21 C22 . . . . 90.3(2) ?
C11 C12 C21 C22 . . . . -91.3(2) ?
C13 C12 C21 C26 . . . . -87.1(2) ?
C11 C12 C21 C26 . . . . 91.3(2) ?
C26 C21 C22 C23 . . . . -4.4(3) ?
C12 C21 C22 C23 . . . . 178.32(18) ?
C26 C21 C22 C27 . . . . 172.23(18) ?
C12 C21 C22 C27 . . . . -5.1(3) ?
C21 C22 C23 C24 . . . . 1.4(3) ?
C27 C22 C23 C24 . . . . -175.3(2) ?
C22 C23 C24 C25 . . . . 1.6(3) ?
C22 C23 C24 C28 . . . . -179.1(2) ?
C23 C24 C25 C26 . . . . -1.6(3) ?
C28 C24 C25 C26 . . . . 179.1(2) ?
C24 C25 C26 C21 . . . . -1.3(3) ?
C24 C25 C26 C29 . . . . 178.51(19) ?
C22 C21 C26 C25 . . . . 4.3(3) ?
C12 C21 C26 C25 . . . . -178.28(17) ?
C22 C21 C26 C29 . . . . -175.46(18) ?
C12 C21 C26 C29 . . . . 1.9(3) ?
C15 C16 C31 C32 . . . . -79.7(2) ?
C11 C16 C31 C32 . . . . 97.0(2) ?
C15 C16 C31 C36 . . . . 101.9(2) ?
C11 C16 C31 C36 . . . . -81.4(2) ?
C36 C31 C32 C33 . . . . 0.9(3) ?
C16 C31 C32 C33 . . . . -177.45(18) ?
C36 C31 C32 C37 . . . . -179.58(19) ?
C16 C31 C32 C37 . . . . 2.0(3) ?
C31 C32 C33 C34 . . . . 0.9(3) ?
C37 C32 C33 C34 . . . . -178.6(2) ?
C32 C33 C34 C35 . . . . -1.7(3) ?
C32 C33 C34 C38 . . . . 176.6(2) ?
C33 C34 C35 C36 . . . . 0.7(3) ?
C38 C34 C35 C36 . . . . -177.6(2) ?
C34 C35 C36 C31 . . . . 1.0(3) ?
C34 C35 C36 C39 . . . . -179.59(19) ?
C32 C31 C36 C35 . . . . -1.9(3) ?
C16 C31 C36 C35 . . . . 176.47(17) ?
C32 C31 C36 C39 . . . . 178.76(18) ?
C16 C31 C36 C39 . . . . -2.9(3) ?
C51 B1 C41 C42 . . . . 114.3(2) ?
C2 B1 C41 C42 . . . . -11.9(3) ?
C51 B1 C41 C46 . . . . -71.3(2) ?
C2 B1 C41 C46 . . . . 162.48(17) ?
C46 C41 C42 F42 . . . . 176.20(18) ?
B1 C41 C42 F42 . . . . -9.2(3) ?
C46 C41 C42 C43 . . . . -5.1(3) ?
B1 C41 C42 C43 . . . . 169.5(2) ?
F42 C42 C43 F43 . . . . 3.3(3) ?
C41 C42 C43 F43 . . . . -175.4(2) ?
F42 C42 C43 C44 . . . . -177.0(2) ?
C41 C42 C43 C44 . . . . 4.3(4) ?
F43 C43 C44 F44 . . . . 0.0(4) ?
C42 C43 C44 F44 . . . . -179.7(2) ?
F43 C43 C44 C45 . . . . 179.5(2) ?
C42 C43 C44 C45 . . . . -0.2(4) ?
F44 C44 C45 F45 . . . . -2.1(3) ?
C43 C44 C45 F45 . . . . 178.5(2) ?
F44 C44 C45 C46 . . . . 177.1(2) ?
C43 C44 C45 C46 . . . . -2.4(3) ?
F45 C45 C46 F46 . . . . 1.5(3) ?
C44 C45 C46 F46 . . . . -177.66(19) ?
F45 C45 C46 C41 . . . . -179.57(19) ?
C44 C45 C46 C41 . . . . 1.3(3) ?
C42 C41 C46 F46 . . . . -178.77(17) ?
B1 C41 C46 F46 . . . . 6.0(3) ?
C42 C41 C46 C45 . . . . 2.3(3) ?
B1 C41 C46 C45 . . . . -172.88(19) ?
C2 B1 C51 C56 . . . . -113.7(2) ?
C41 B1 C51 C56 . . . . 116.9(2) ?
C2 B1 C51 C52 . . . . 63.4(2) ?
C41 B1 C51 C52 . . . . -66.0(2) ?
C56 C51 C52 F52 . . . . -179.73(17) ?
B1 C51 C52 F52 . . . . 2.9(3) ?
C56 C51 C52 C53 . . . . 1.0(3) ?
B1 C51 C52 C53 . . . . -176.43(18) ?
F52 C52 C53 F53 . . . . -0.2(3) ?
C51 C52 C53 F53 . . . . 179.14(19) ?
F52 C52 C53 C54 . . . . -179.47(19) ?
C51 C52 C53 C54 . . . . -0.2(3) ?
F53 C53 C54 F54 . . . . -1.3(3) ?
C52 C53 C54 F54 . . . . 178.0(2) ?
F53 C53 C54 C55 . . . . 179.7(2) ?
C52 C53 C54 C55 . . . . -1.0(3) ?
F54 C54 C55 F55 . . . . 0.7(4) ?
C53 C54 C55 F55 . . . . 179.6(2) ?
F54 C54 C55 C56 . . . . -177.7(2) ?
C53 C54 C55 C56 . . . . 1.2(4) ?
C52 C51 C56 F56 . . . . -179.80(18) ?
B1 C51 C56 F56 . . . . -2.5(3) ?
C52 C51 C56 C55 . . . . -0.7(3) ?
B1 C51 C56 C55 . . . . 176.6(2) ?
F55 C55 C56 F56 . . . . 0.4(3) ?
C54 C55 C56 F56 . . . . 178.8(2) ?
F55 C55 C56 C51 . . . . -178.7(2) ?
C54 C55 C56 C51 . . . . -0.4(4) ?
C61 C62 C63 C64 . . . . -179.8(6) ?
C62 C63 C64 C65 . . . . -175.8(6) ?
C61A C62A C63A C64A . . . . 179.3(12) ?
C62A C63A C64A C65A . . . . 172.4(13) ?


####################################################################### 
# 
# 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_erk9555
_database_code_depnum_ccdc_archive 'CCDC 1953117'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-09-12 deposited with the CCDC.	2020-06-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H31 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         398.50

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1976(4)
_cell_length_b                   18.0312(7)
_cell_length_c                   15.7056(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.521(2)
_cell_angle_gamma                90
_cell_volume                     2247.33(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9934
_cell_measurement_theta_min      2.5666
_cell_measurement_theta_max      27.3596
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.118
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856

_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            41145
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;

Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             5143
_reflns_number_gt                4479
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1087
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_number_reflns         5143
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+1.9041P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.282
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.45167(5) 0.31712(2) 0.68715(3) 0.01336(10) Uani d . . . 1 . .
C C1 0.3052(2) 0.24071(8) 0.63846(10) 0.0188(3) Uani d . . . 1 . .
H H1A 0.1921 0.2482 0.6488 0.023 Uiso calc U . R 1 . .
H H1B 0.2945 0.2359 0.5745 0.023 Uiso calc U . R 1 . .
C C2 0.3922(2) 0.17449(8) 0.68794(11) 0.0198(3) Uani d . . . 1 . .
H H2 0.3773 0.1258 0.6643 0.024 Uiso calc U . R 1 . .
C C3 0.4922(2) 0.18895(8) 0.76780(10) 0.0186(3) Uani d . . . 1 . .
H H3 0.5544 0.1513 0.8043 0.022 Uiso calc U . R 1 . .
C C4 0.4989(2) 0.26905(8) 0.79546(10) 0.0175(3) Uani d . . . 1 . .
H H4A 0.6117 0.2826 0.8321 0.021 Uiso calc U . R 1 . .
H H4B 0.413 0.2803 0.8281 0.021 Uiso calc U . R 1 . .
C C11 0.32193(17) 0.39915(7) 0.69611(9) 0.0117(3) Uani d . . . 1 . .
C C12 0.18545(18) 0.42090(8) 0.62553(9) 0.0132(3) Uani d . . . 1 . .
C C13 0.10002(19) 0.48693(8) 0.63070(10) 0.0170(3) Uani d . . . 1 . .
H H13 0.0073 0.5005 0.5836 0.02 Uiso calc U . R 1 . .
C C14 0.1478(2) 0.53322(8) 0.70324(10) 0.0189(3) Uani d . . . 1 . .
H H14 0.0881 0.5779 0.7061 0.023 Uiso calc U . R 1 . .
C C15 0.28313(19) 0.51345(8) 0.77131(10) 0.0167(3) Uani d . . . 1 . .
H H15 0.3165 0.5453 0.8208 0.02 Uiso calc U . R 1 . .
C C16 0.37213(18) 0.44768(8) 0.76895(9) 0.0129(3) Uani d . . . 1 . .
C C21 0.12951(18) 0.37612(8) 0.54264(9) 0.0129(3) Uani d . . . 1 . .
C C22 0.22589(18) 0.37592(8) 0.48037(10) 0.0144(3) Uani d . . . 1 . .
C C23 0.17349(19) 0.33277(8) 0.40453(10) 0.0157(3) Uani d . . . 1 . .
H H23 0.2396 0.3325 0.3627 0.019 Uiso calc U . R 1 . .
C C24 0.02752(19) 0.29031(8) 0.38849(10) 0.0160(3) Uani d . . . 1 . .
C C25 -0.06953(18) 0.29338(8) 0.44971(10) 0.0157(3) Uani d . . . 1 . .
H H25 -0.171 0.2655 0.4392 0.019 Uiso calc U . R 1 . .
C C26 -0.02235(18) 0.33603(8) 0.52572(9) 0.0140(3) Uani d . . . 1 . .
C C27 0.3812(2) 0.42357(9) 0.49156(11) 0.0209(3) Uani d . . . 1 . .
H H27A 0.4706 0.4043 0.5402 0.031 Uiso calc U . R 1 . .
H H27B 0.3544 0.4746 0.5046 0.031 Uiso calc U . R 1 . .
H H27C 0.4193 0.4227 0.4372 0.031 Uiso calc U . R 1 . .
C C28 -0.0280(2) 0.24504(9) 0.30565(11) 0.0223(3) Uani d . . . 1 . .
H H28A -0.1162 0.2718 0.2631 0.033 Uiso calc U . R 1 . .
H H28B -0.0724 0.1973 0.3195 0.033 Uiso calc U . R 1 . .
H H28C 0.0684 0.2365 0.2805 0.033 Uiso calc U . R 1 . .
C C29 -0.13575(19) 0.33839(9) 0.58788(10) 0.0195(3) Uani d . . . 1 . .
H H29A -0.2024 0.3841 0.5782 0.029 Uiso calc U . R 1 . .
H H29B -0.067 0.3371 0.6487 0.029 Uiso calc U . R 1 . .
H H29C -0.2115 0.2955 0.5772 0.029 Uiso calc U . R 1 . .
C C31 0.51880(18) 0.43251(8) 0.84562(9) 0.0128(3) Uani d . . . 1 . .
C C32 0.68495(19) 0.44436(8) 0.83887(10) 0.0155(3) Uani d . . . 1 . .
C C33 0.81860(19) 0.42897(8) 0.91117(11) 0.0183(3) Uani d . . . 1 . .
H H33 0.9306 0.4372 0.9066 0.022 Uiso calc U . R 1 . .
C C34 0.79299(19) 0.40192(8) 0.98999(10) 0.0185(3) Uani d . . . 1 . .
C C35 0.6275(2) 0.39192(8) 0.99578(10) 0.0169(3) Uani d . . . 1 . .
H H35 0.6077 0.3737 1.049 0.02 Uiso calc U . R 1 . .
C C36 0.49038(18) 0.40795(8) 0.92566(10) 0.0145(3) Uani d . . . 1 . .
C C37 0.7210(2) 0.47358(9) 0.75525(11) 0.0210(3) Uani d . . . 1 . .
H H37A 0.8408 0.4861 0.7662 0.031 Uiso calc U . R 1 . .
H H37B 0.653 0.518 0.736 0.031 Uiso calc U . R 1 . .
H H37C 0.6925 0.4355 0.7093 0.031 Uiso calc U . R 1 . .
C C38 0.9395(2) 0.38449(10) 1.06702(12) 0.0271(4) Uani d . . . 1 . .
H H38A 0.9586 0.4262 1.1083 0.041 Uiso calc U . R 1 . .
H H38B 1.0409 0.3761 1.046 0.041 Uiso calc U . R 1 . .
H H38C 0.9143 0.3398 1.0968 0.041 Uiso calc U . R 1 . .
C C39 0.31405(19) 0.39751(9) 0.93698(10) 0.0191(3) Uani d . . . 1 . .
H H39A 0.316 0.3608 0.9833 0.029 Uiso calc U . R 1 . .
H H39B 0.24 0.3801 0.8816 0.029 Uiso calc U . R 1 . .
H H39C 0.2719 0.4449 0.9535 0.029 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C11 . 1.8476(14) ?
P1 C1 . 1.8611(16) ?
P1 C4 . 1.8613(16) ?
C1 C2 . 1.503(2) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.341(2) ?
C2 H2 . 0.95 ?
C3 C4 . 1.505(2) ?
C3 H3 . 0.95 ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C11 C16 . 1.4171(19) ?
C11 C12 . 1.4185(19) ?
C12 C13 . 1.394(2) ?
C12 C21 . 1.5026(19) ?
C13 C14 . 1.387(2) ?
C13 H13 . 0.95 ?
C14 C15 . 1.381(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.398(2) ?
C15 H15 . 0.95 ?
C16 C31 . 1.4981(19) ?
C21 C22 . 1.403(2) ?
C21 C26 . 1.406(2) ?
C22 C23 . 1.397(2) ?
C22 C27 . 1.509(2) ?
C23 C24 . 1.389(2) ?
C23 H23 . 0.95 ?
C24 C25 . 1.394(2) ?
C24 C28 . 1.507(2) ?
C25 C26 . 1.391(2) ?
C25 H25 . 0.95 ?
C26 C29 . 1.508(2) ?
C27 H27A . 0.98 ?
C27 H27B . 0.98 ?
C27 H27C . 0.98 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C29 H29A . 0.98 ?
C29 H29B . 0.98 ?
C29 H29C . 0.98 ?
C31 C36 . 1.406(2) ?
C31 C32 . 1.409(2) ?
C32 C33 . 1.394(2) ?
C32 C37 . 1.511(2) ?
C33 C34 . 1.395(2) ?
C33 H33 . 0.95 ?
C34 C35 . 1.394(2) ?
C34 C38 . 1.509(2) ?
C35 C36 . 1.392(2) ?
C35 H35 . 0.95 ?
C36 C39 . 1.512(2) ?
C37 H37A . 0.98 ?
C37 H37B . 0.98 ?
C37 H37C . 0.98 ?
C38 H38A . 0.98 ?
C38 H38B . 0.98 ?
C38 H38C . 0.98 ?
C39 H39A . 0.98 ?
C39 H39B . 0.98 ?
C39 H39C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 P1 C1 . . 107.43(7) ?
C11 P1 C4 . . 107.16(7) ?
C1 P1 C4 . . 89.75(7) ?
C2 C1 P1 . . 101.67(10) ?
C2 C1 H1A . . 111.4 ?
P1 C1 H1A . . 111.4 ?
C2 C1 H1B . . 111.4 ?
P1 C1 H1B . . 111.4 ?
H1A C1 H1B . . 109.3 ?
C3 C2 C1 . . 115.37(13) ?
C3 C2 H2 . . 122.3 ?
C1 C2 H2 . . 122.3 ?
C2 C3 C4 . . 115.22(13) ?
C2 C3 H3 . . 122.4 ?
C4 C3 H3 . . 122.4 ?
C3 C4 P1 . . 101.48(10) ?
C3 C4 H4A . . 111.5 ?
P1 C4 H4A . . 111.5 ?
C3 C4 H4B . . 111.5 ?
P1 C4 H4B . . 111.5 ?
H4A C4 H4B . . 109.3 ?
C16 C11 C12 . . 118.20(12) ?
C16 C11 P1 . . 119.98(10) ?
C12 C11 P1 . . 121.21(11) ?
C13 C12 C11 . . 120.00(13) ?
C13 C12 C21 . . 117.43(13) ?
C11 C12 C21 . . 122.55(12) ?
C14 C13 C12 . . 121.28(14) ?
C14 C13 H13 . . 119.4 ?
C12 C13 H13 . . 119.4 ?
C15 C14 C13 . . 119.15(14) ?
C15 C14 H14 . . 120.4 ?
C13 C14 H14 . . 120.4 ?
C14 C15 C16 . . 121.47(14) ?
C14 C15 H15 . . 119.3 ?
C16 C15 H15 . . 119.3 ?
C15 C16 C11 . . 119.84(13) ?
C15 C16 C31 . . 116.92(13) ?
C11 C16 C31 . . 123.25(12) ?
C22 C21 C26 . . 119.58(13) ?
C22 C21 C12 . . 120.16(13) ?
C26 C21 C12 . . 120.23(13) ?
C23 C22 C21 . . 119.29(13) ?
C23 C22 C27 . . 119.11(14) ?
C21 C22 C27 . . 121.56(13) ?
C24 C23 C22 . . 121.88(14) ?
C24 C23 H23 . . 119.1 ?
C22 C23 H23 . . 119.1 ?
C23 C24 C25 . . 117.88(14) ?
C23 C24 C28 . . 121.01(14) ?
C25 C24 C28 . . 121.06(14) ?
C26 C25 C24 . . 121.99(14) ?
C26 C25 H25 . . 119.0 ?
C24 C25 H25 . . 119.0 ?
C25 C26 C21 . . 119.27(14) ?
C25 C26 C29 . . 119.16(13) ?
C21 C26 C29 . . 121.56(13) ?
C22 C27 H27A . . 109.5 ?
C22 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C22 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C24 C28 H28A . . 109.5 ?
C24 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C24 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C26 C29 H29A . . 109.5 ?
C26 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
C26 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
C36 C31 C32 . . 119.67(13) ?
C36 C31 C16 . . 119.77(13) ?
C32 C31 C16 . . 120.54(13) ?
C33 C32 C31 . . 119.07(14) ?
C33 C32 C37 . . 119.49(14) ?
C31 C32 C37 . . 121.43(13) ?
C32 C33 C34 . . 122.02(14) ?
C32 C33 H33 . . 119.0 ?
C34 C33 H33 . . 119.0 ?
C35 C34 C33 . . 117.95(14) ?
C35 C34 C38 . . 120.86(15) ?
C33 C34 C38 . . 121.19(15) ?
C36 C35 C34 . . 121.83(15) ?
C36 C35 H35 . . 119.1 ?
C34 C35 H35 . . 119.1 ?
C35 C36 C31 . . 119.38(14) ?
C35 C36 C39 . . 119.15(14) ?
C31 C36 C39 . . 121.46(13) ?
C32 C37 H37A . . 109.5 ?
C32 C37 H37B . . 109.5 ?
H37A C37 H37B . . 109.5 ?
C32 C37 H37C . . 109.5 ?
H37A C37 H37C . . 109.5 ?
H37B C37 H37C . . 109.5 ?
C34 C38 H38A . . 109.5 ?
C34 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C34 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C36 C39 H39A . . 109.5 ?
C36 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C36 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 P1 C1 C2 . . . . -142.70(10) ?
C4 P1 C1 C2 . . . . -34.77(11) ?
P1 C1 C2 C3 . . . . 26.01(17) ?
C1 C2 C3 C4 . . . . 0.9(2) ?
C2 C3 C4 P1 . . . . -27.38(17) ?
C11 P1 C4 C3 . . . . 143.37(10) ?
C1 P1 C4 C3 . . . . 35.17(11) ?
C1 P1 C11 C16 . . . . 143.70(12) ?
C4 P1 C11 C16 . . . . 48.42(13) ?
C1 P1 C11 C12 . . . . -45.43(13) ?
C4 P1 C11 C12 . . . . -140.71(12) ?
C16 C11 C12 C13 . . . . -2.7(2) ?
P1 C11 C12 C13 . . . . -173.76(11) ?
C16 C11 C12 C21 . . . . 175.82(13) ?
P1 C11 C12 C21 . . . . 4.79(19) ?
C11 C12 C13 C14 . . . . 1.3(2) ?
C21 C12 C13 C14 . . . . -177.31(14) ?
C12 C13 C14 C15 . . . . 0.3(2) ?
C13 C14 C15 C16 . . . . -0.5(2) ?
C14 C15 C16 C11 . . . . -1.0(2) ?
C14 C15 C16 C31 . . . . 178.89(14) ?
C12 C11 C16 C15 . . . . 2.6(2) ?
P1 C11 C16 C15 . . . . 173.73(11) ?
C12 C11 C16 C31 . . . . -177.32(13) ?
P1 C11 C16 C31 . . . . -6.18(19) ?
C13 C12 C21 C22 . . . . 104.36(16) ?
C11 C12 C21 C22 . . . . -74.23(18) ?
C13 C12 C21 C26 . . . . -73.66(18) ?
C11 C12 C21 C26 . . . . 107.76(16) ?
C26 C21 C22 C23 . . . . -3.2(2) ?
C12 C21 C22 C23 . . . . 178.74(13) ?
C26 C21 C22 C27 . . . . 174.29(13) ?
C12 C21 C22 C27 . . . . -3.7(2) ?
C21 C22 C23 C24 . . . . 0.5(2) ?
C27 C22 C23 C24 . . . . -177.07(14) ?
C22 C23 C24 C25 . . . . 1.7(2) ?
C22 C23 C24 C28 . . . . 179.11(14) ?
C23 C24 C25 C26 . . . . -1.3(2) ?
C28 C24 C25 C26 . . . . -178.65(14) ?
C24 C25 C26 C21 . . . . -1.4(2) ?
C24 C25 C26 C29 . . . . 178.36(14) ?
C22 C21 C26 C25 . . . . 3.7(2) ?
C12 C21 C26 C25 . . . . -178.31(13) ?
C22 C21 C26 C29 . . . . -176.10(13) ?
C12 C21 C26 C29 . . . . 1.9(2) ?
C15 C16 C31 C36 . . . . 76.11(18) ?
C11 C16 C31 C36 . . . . -103.98(17) ?
C15 C16 C31 C32 . . . . -102.35(16) ?
C11 C16 C31 C32 . . . . 77.56(19) ?
C36 C31 C32 C33 . . . . 2.2(2) ?
C16 C31 C32 C33 . . . . -179.36(13) ?
C36 C31 C32 C37 . . . . -177.58(13) ?
C16 C31 C32 C37 . . . . 0.9(2) ?
C31 C32 C33 C34 . . . . 0.3(2) ?
C37 C32 C33 C34 . . . . -179.99(14) ?
C32 C33 C34 C35 . . . . -1.4(2) ?
C32 C33 C34 C38 . . . . 179.04(14) ?
C33 C34 C35 C36 . . . . 0.2(2) ?
C38 C34 C35 C36 . . . . 179.71(14) ?
C34 C35 C36 C31 . . . . 2.2(2) ?
C34 C35 C36 C39 . . . . -178.62(14) ?
C32 C31 C36 C35 . . . . -3.4(2) ?
C16 C31 C36 C35 . . . . 178.14(13) ?
C32 C31 C36 C39 . . . . 177.48(13) ?
C16 C31 C36 C39 . . . . -1.0(2) ?


####################################################################### 
# 
# 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_erk9472
_database_code_depnum_ccdc_archive 'CCDC 1953120'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-09-12 deposited with the CCDC.	2020-06-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C55 H44 B F10 O P'
_chemical_formula_iupac          ?
_chemical_formula_weight         952.68

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0862(3)
_cell_length_b                   17.6699(4)
_cell_length_c                   21.1798(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.9670(10)
_cell_angle_gamma                90
_cell_volume                     4454.93(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      3.2778
_cell_measurement_theta_max      66.5595
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1968

_exptl_absorpt_coefficient_mu    1.273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            62367
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_theta_min         4.24
_diffrn_reflns_theta_max         66.74
_diffrn_reflns_theta_full        66.74
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;

Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             7865
_reflns_number_gt                6395
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1021
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_number_reflns         7865
_refine_ls_number_parameters     619
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+1.3930P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.334
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.54753(4) 0.70220(3) 0.70236(2) 0.01551(12) Uani d . . . 1 . .
C C1 0.49285(15) 0.63466(10) 0.64001(9) 0.0176(4) Uani d . . . 1 . .
H H1A 0.4535 0.6612 0.6014 0.021 Uiso calc U . R 1 . .
H H1B 0.5546 0.6041 0.6279 0.021 Uiso calc U . R 1 . .
C C2 0.40996(15) 0.58348(10) 0.66890(9) 0.0179(4) Uani d . . . 1 . .
H H2 0.4101 0.5326 0.6481 0.021 Uiso calc U . R 1 . .
C C4 0.50137(15) 0.65254(10) 0.76822(9) 0.0172(4) Uani d . . . 1 . .
H H4A 0.5635 0.6477 0.8052 0.021 Uiso calc U . R 1 . .
H H4B 0.4379 0.6793 0.7823 0.021 Uiso calc U . R 1 . .
C C3 0.46433(16) 0.57414(10) 0.74001(9) 0.0193(4) Uani d . . . 1 . .
H H3A 0.4097 0.5513 0.7642 0.023 Uiso calc U . R 1 . .
H H3B 0.5302 0.5401 0.7436 0.023 Uiso calc U . R 1 . .
B B1 0.28085(18) 0.61519(12) 0.65462(10) 0.0181(5) Uani d . . . 1 . .
O O1 0.28107(11) 0.69935(7) 0.66875(6) 0.0180(3) Uani d . . . 1 . .
C C5 0.48032(16) 0.79758(10) 0.69467(9) 0.0185(4) Uani d . . . 1 . .
H H5 0.5391 0.8325 0.6834 0.022 Uiso calc U . R 1 . .
C C6 0.38502(16) 0.80186(10) 0.63897(9) 0.0188(4) Uani d . . . 1 . .
H H6 0.3878 0.8419 0.6093 0.023 Uiso calc U . R 1 . .
C C7 0.29679(16) 0.75537(10) 0.62667(9) 0.0181(4) Uani d . . . 1 . .
C C11 0.69862(15) 0.71643(10) 0.70484(9) 0.0155(4) Uani d . . . 1 . .
C C12 0.78205(15) 0.68810(10) 0.75434(9) 0.0170(4) Uani d . . . 1 . .
C C13 0.89475(16) 0.70364(11) 0.75258(9) 0.0200(4) Uani d . . . 1 . .
H H13 0.9507 0.6865 0.7867 0.024 Uiso calc U . R 1 . .
C C14 0.92685(16) 0.74300(11) 0.70281(9) 0.0219(4) Uani d . . . 1 . .
H H14 1.0041 0.7527 0.7026 0.026 Uiso calc U . R 1 . .
C C15 0.84632(16) 0.76824(11) 0.65330(9) 0.0219(4) Uani d . . . 1 . .
H H15 0.8691 0.7945 0.6186 0.026 Uiso calc U . R 1 . .
C C16 0.73259(16) 0.75628(10) 0.65276(9) 0.0182(4) Uani d . . . 1 . .
C C21 0.76394(15) 0.63722(10) 0.80870(9) 0.0168(4) Uani d . . . 1 . .
C C22 0.76284(15) 0.55880(11) 0.79866(9) 0.0198(4) Uani d . . . 1 . .
C C23 0.75650(16) 0.51063(11) 0.84997(10) 0.0227(4) Uani d . . . 1 . .
H H23 0.7546 0.4575 0.8431 0.027 Uiso calc U . R 1 . .
C C24 0.75290(16) 0.53845(11) 0.91123(10) 0.0220(4) Uani d . . . 1 . .
C C25 0.75579(15) 0.61649(11) 0.91987(9) 0.0192(4) Uani d . . . 1 . .
H H25 0.7531 0.6363 0.9613 0.023 Uiso calc U . R 1 . .
C C26 0.76244(15) 0.66650(11) 0.87014(9) 0.0177(4) Uani d . . . 1 . .
C C27 0.77349(18) 0.52555(11) 0.73410(10) 0.0252(5) Uani d . . . 1 . .
H H27A 0.7082 0.5403 0.7023 0.038 Uiso calc U . R 1 . .
H H27B 0.777 0.4702 0.7373 0.038 Uiso calc U . R 1 . .
H H27C 0.8422 0.5446 0.7209 0.038 Uiso calc U . R 1 . .
C C28 0.75000(19) 0.48558(12) 0.96688(10) 0.0312(5) Uani d . . . 1 . .
H H28A 0.7746 0.5127 1.0072 0.047 Uiso calc U . R 1 . .
H H28B 0.8003 0.4427 0.9641 0.047 Uiso calc U . R 1 . .
H H28C 0.6732 0.467 0.9655 0.047 Uiso calc U . R 1 . .
C C29 0.76893(17) 0.75038(11) 0.88350(10) 0.0238(4) Uani d . . . 1 . .
H H29A 0.693 0.7719 0.8759 0.036 Uiso calc U . R 1 . .
H H29B 0.8141 0.7748 0.8551 0.036 Uiso calc U . R 1 . .
H H29C 0.8038 0.759 0.9282 0.036 Uiso calc U . R 1 . .
C C31 0.65394(15) 0.78502(11) 0.59471(9) 0.0184(4) Uani d . . . 1 . .
C C32 0.62054(16) 0.73698(11) 0.54175(9) 0.0189(4) Uani d . . . 1 . .
C C33 0.54840(16) 0.76544(11) 0.48813(9) 0.0203(4) Uani d . . . 1 . .
H H33 0.5236 0.7325 0.4531 0.024 Uiso calc U . R 1 . .
C C34 0.51190(16) 0.83997(11) 0.48433(9) 0.0206(4) Uani d . . . 1 . .
C C35 0.55250(16) 0.88755(11) 0.53527(9) 0.0200(4) Uani d . . . 1 . .
H H35 0.5308 0.9393 0.5328 0.024 Uiso calc U . R 1 . .
C C36 0.62357(16) 0.86207(11) 0.58961(9) 0.0192(4) Uani d . . . 1 . .
C C37 0.66623(17) 0.65794(11) 0.53873(10) 0.0245(4) Uani d . . . 1 . .
H H37A 0.7185 0.6566 0.5082 0.037 Uiso calc U . R 1 . .
H H37B 0.6041 0.6228 0.5248 0.037 Uiso calc U . R 1 . .
H H37C 0.7058 0.6431 0.5813 0.037 Uiso calc U . R 1 . .
C C38 0.43435(18) 0.86938(12) 0.42596(10) 0.0274(5) Uani d . . . 1 . .
H H38A 0.4105 0.8274 0.3965 0.041 Uiso calc U . R 1 . .
H H38B 0.4739 0.9072 0.4044 0.041 Uiso calc U . R 1 . .
H H38C 0.3683 0.8926 0.4391 0.041 Uiso calc U . R 1 . .
C C39 0.66885(18) 0.91908(12) 0.64064(10) 0.0271(5) Uani d . . . 1 . .
H H39A 0.7264 0.9501 0.6258 0.041 Uiso calc U . R 1 . .
H H39B 0.702 0.8925 0.68 0.041 Uiso calc U . R 1 . .
H H39C 0.6075 0.9516 0.6493 0.041 Uiso calc U . R 1 . .
C C41 0.20869(15) 0.57056(10) 0.70303(9) 0.0174(4) Uani d . . . 1 . .
F F42 0.18924(10) 0.67218(6) 0.77475(5) 0.0266(3) Uani d . . . 1 . .
C C42 0.16916(16) 0.59918(10) 0.75589(9) 0.0195(4) Uani d . . . 1 . .
F F43 0.07525(10) 0.58837(6) 0.84524(5) 0.0293(3) Uani d . . . 1 . .
C C43 0.10788(16) 0.55752(11) 0.79324(9) 0.0215(4) Uani d . . . 1 . .
F F44 0.02308(10) 0.44201(7) 0.81442(6) 0.0310(3) Uani d . . . 1 . .
C C44 0.08172(16) 0.48311(11) 0.77816(9) 0.0222(4) Uani d . . . 1 . .
F F45 0.09909(10) 0.37794(6) 0.71260(6) 0.0296(3) Uani d . . . 1 . .
C C45 0.12053(16) 0.45131(10) 0.72698(9) 0.0205(4) Uani d . . . 1 . .
F F46 0.22154(9) 0.45743(6) 0.64397(5) 0.0228(3) Uani d . . . 1 . .
C C46 0.18326(15) 0.49441(11) 0.69221(9) 0.0182(4) Uani d . . . 1 . .
C C51 0.21336(15) 0.59751(10) 0.58088(9) 0.0176(4) Uani d . . . 1 . .
F F52 0.36711(9) 0.54690(6) 0.53634(5) 0.0253(3) Uani d . . . 1 . .
C C52 0.25641(16) 0.56573(11) 0.53037(9) 0.0200(4) Uani d . . . 1 . .
F F53 0.24035(10) 0.51615(7) 0.42486(5) 0.0296(3) Uani d . . . 1 . .
C C53 0.19317(17) 0.54937(11) 0.47098(9) 0.0228(4) Uani d . . . 1 . .
F F54 0.01931(10) 0.55171(8) 0.40122(6) 0.0374(3) Uani d . . . 1 . .
C C54 0.08087(17) 0.56711(11) 0.45881(9) 0.0244(5) Uani d . . . 1 . .
F F55 -0.07785(10) 0.61548(7) 0.49601(6) 0.0341(3) Uani d . . . 1 . .
C C55 0.03269(16) 0.59886(11) 0.50683(10) 0.0243(4) Uani d . . . 1 . .
F F56 0.04428(9) 0.64181(6) 0.61089(5) 0.0250(3) Uani d . . . 1 . .
C C56 0.09830(16) 0.61232(11) 0.56563(9) 0.0208(4) Uani d . . . 1 . .
C C61 0.45676(16) 0.82604(10) 0.75906(9) 0.0192(4) Uani d . . . 1 . .
C C62 0.54322(17) 0.86080(10) 0.80101(9) 0.0214(4) Uani d . . . 1 . .
H H62 0.6149 0.8665 0.789 0.026 Uiso calc U . R 1 . .
C C63 0.52599(18) 0.88722(11) 0.86018(10) 0.0249(4) Uani d . . . 1 . .
H H63 0.586 0.9102 0.8886 0.03 Uiso calc U . R 1 . .
C C64 0.42161(18) 0.88008(11) 0.87782(10) 0.0270(5) Uani d . . . 1 . .
H H64 0.4096 0.8984 0.9182 0.032 Uiso calc U . R 1 . .
C C65 0.33418(18) 0.84595(11) 0.83619(10) 0.0268(5) Uani d . . . 1 . .
H H65 0.2624 0.841 0.8482 0.032 Uiso calc U . R 1 . .
C C66 0.35163(17) 0.81905(11) 0.77701(10) 0.0234(4) Uani d . . . 1 . .
H H66 0.2917 0.7958 0.7487 0.028 Uiso calc U . R 1 . .
C C71 0.20912(16) 0.77086(11) 0.56917(9) 0.0202(4) Uani d . . . 1 . .
C C72 0.23414(17) 0.76451(11) 0.50752(10) 0.0232(4) Uani d . . . 1 . .
H H72 0.3059 0.7466 0.5019 0.028 Uiso calc U . R 1 . .
C C73 0.15572(18) 0.78399(12) 0.45473(11) 0.0297(5) Uani d . . . 1 . .
H H73 0.1732 0.7786 0.4129 0.036 Uiso calc U . R 1 . .
C C74 0.05144(18) 0.81144(13) 0.46237(11) 0.0348(6) Uani d . . . 1 . .
H H74 -0.0024 0.8252 0.426 0.042 Uiso calc U . R 1 . .
C C75 0.02638(18) 0.81871(14) 0.52330(11) 0.0382(6) Uani d . . . 1 . .
H H75 -0.045 0.8375 0.5287 0.046 Uiso calc U . R 1 . .
C C76 0.10443(17) 0.79880(12) 0.57647(10) 0.0287(5) Uani d . . . 1 . .
H H76 0.0865 0.8042 0.6182 0.034 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C4 . 1.8155(19) ?
P1 C1 . 1.8173(19) ?
P1 C11 . 1.8351(18) ?
P1 C5 . 1.8659(19) ?
C1 C2 . 1.552(3) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.544(3) ?
C2 B1 . 1.636(3) ?
C2 H2 . 1.0 ?
C4 C3 . 1.544(3) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
B1 O1 . 1.517(2) ?
B1 C41 . 1.656(3) ?
B1 C51 . 1.662(3) ?
O1 C7 . 1.367(2) ?
C5 C6 . 1.501(3) ?
C5 C61 . 1.526(3) ?
C5 H5 . 1.0 ?
C6 C7 . 1.336(3) ?
C6 H6 . 0.95 ?
C7 C71 . 1.495(3) ?
C11 C12 . 1.414(3) ?
C11 C16 . 1.428(3) ?
C12 C13 . 1.396(3) ?
C12 C21 . 1.506(3) ?
C13 C14 . 1.374(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.376(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.389(3) ?
C15 H15 . 0.95 ?
C16 C31 . 1.506(3) ?
C21 C22 . 1.402(3) ?
C21 C26 . 1.403(3) ?
C22 C23 . 1.393(3) ?
C22 C27 . 1.514(3) ?
C23 C24 . 1.395(3) ?
C23 H23 . 0.95 ?
C24 C25 . 1.391(3) ?
C24 C28 . 1.509(3) ?
C25 C26 . 1.388(3) ?
C25 H25 . 0.95 ?
C26 C29 . 1.508(3) ?
C27 H27A . 0.98 ?
C27 H27B . 0.98 ?
C27 H27C . 0.98 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C29 H29A . 0.98 ?
C29 H29B . 0.98 ?
C29 H29C . 0.98 ?
C31 C32 . 1.409(3) ?
C31 C36 . 1.409(3) ?
C32 C33 . 1.400(3) ?
C32 C37 . 1.507(3) ?
C33 C34 . 1.387(3) ?
C33 H33 . 0.95 ?
C34 C35 . 1.389(3) ?
C34 C38 . 1.509(3) ?
C35 C36 . 1.387(3) ?
C35 H35 . 0.95 ?
C36 C39 . 1.509(3) ?
C37 H37A . 0.98 ?
C37 H37B . 0.98 ?
C37 H37C . 0.98 ?
C38 H38A . 0.98 ?
C38 H38B . 0.98 ?
C38 H38C . 0.98 ?
C39 H39A . 0.98 ?
C39 H39B . 0.98 ?
C39 H39C . 0.98 ?
C41 C42 . 1.387(3) ?
C41 C46 . 1.390(3) ?
F42 C42 . 1.360(2) ?
C42 C43 . 1.385(3) ?
F43 C43 . 1.348(2) ?
C43 C44 . 1.377(3) ?
F44 C44 . 1.344(2) ?
C44 C45 . 1.374(3) ?
F45 C45 . 1.347(2) ?
C45 C46 . 1.375(3) ?
F46 C46 . 1.360(2) ?
C51 C52 . 1.387(3) ?
C51 C56 . 1.397(3) ?
F52 C52 . 1.363(2) ?
C52 C53 . 1.385(3) ?
F53 C53 . 1.348(2) ?
C53 C54 . 1.373(3) ?
F54 C54 . 1.342(2) ?
C54 C55 . 1.376(3) ?
F55 C55 . 1.348(2) ?
C55 C56 . 1.376(3) ?
F56 C56 . 1.354(2) ?
C61 C62 . 1.392(3) ?
C61 C66 . 1.393(3) ?
C62 C63 . 1.386(3) ?
C62 H62 . 0.95 ?
C63 C64 . 1.382(3) ?
C63 H63 . 0.95 ?
C64 C65 . 1.391(3) ?
C64 H64 . 0.95 ?
C65 C66 . 1.390(3) ?
C65 H65 . 0.95 ?
C66 H66 . 0.95 ?
C71 C76 . 1.392(3) ?
C71 C72 . 1.395(3) ?
C72 C73 . 1.378(3) ?
C72 H72 . 0.95 ?
C73 C74 . 1.386(3) ?
C73 H73 . 0.95 ?
C74 C75 . 1.382(3) ?
C74 H74 . 0.95 ?
C75 C76 . 1.383(3) ?
C75 H75 . 0.95 ?
C76 H76 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 P1 C1 . . 96.86(9) ?
C4 P1 C11 . . 118.74(9) ?
C1 P1 C11 . . 110.23(8) ?
C4 P1 C5 . . 108.45(9) ?
C1 P1 C5 . . 115.58(9) ?
C11 P1 C5 . . 107.14(8) ?
C2 C1 P1 . . 105.94(12) ?
C2 C1 H1A . . 110.5 ?
P1 C1 H1A . . 110.5 ?
C2 C1 H1B . . 110.5 ?
P1 C1 H1B . . 110.5 ?
H1A C1 H1B . . 108.7 ?
C3 C2 C1 . . 104.60(15) ?
C3 C2 B1 . . 116.62(15) ?
C1 C2 B1 . . 112.81(15) ?
C3 C2 H2 . . 107.5 ?
C1 C2 H2 . . 107.5 ?
B1 C2 H2 . . 107.5 ?
C3 C4 P1 . . 104.08(13) ?
C3 C4 H4A . . 110.9 ?
P1 C4 H4A . . 110.9 ?
C3 C4 H4B . . 110.9 ?
P1 C4 H4B . . 110.9 ?
H4A C4 H4B . . 109.0 ?
C4 C3 C2 . . 109.12(15) ?
C4 C3 H3A . . 109.9 ?
C2 C3 H3A . . 109.9 ?
C4 C3 H3B . . 109.9 ?
C2 C3 H3B . . 109.9 ?
H3A C3 H3B . . 108.3 ?
O1 B1 C2 . . 109.29(15) ?
O1 B1 C41 . . 109.13(15) ?
C2 B1 C41 . . 108.06(15) ?
O1 B1 C51 . . 110.71(15) ?
C2 B1 C51 . . 114.00(16) ?
C41 B1 C51 . . 105.47(15) ?
C7 O1 B1 . . 125.23(14) ?
C6 C5 C61 . . 116.70(16) ?
C6 C5 P1 . . 112.17(13) ?
C61 C5 P1 . . 111.44(13) ?
C6 C5 H5 . . 105.1 ?
C61 C5 H5 . . 105.1 ?
P1 C5 H5 . . 105.1 ?
C7 C6 C5 . . 126.90(17) ?
C7 C6 H6 . . 116.6 ?
C5 C6 H6 . . 116.6 ?
C6 C7 O1 . . 120.97(17) ?
C6 C7 C71 . . 118.41(17) ?
O1 C7 C71 . . 120.32(16) ?
C12 C11 C16 . . 118.94(16) ?
C12 C11 P1 . . 123.43(14) ?
C16 C11 P1 . . 117.60(14) ?
C13 C12 C11 . . 118.96(17) ?
C13 C12 C21 . . 114.16(16) ?
C11 C12 C21 . . 126.77(16) ?
C14 C13 C12 . . 121.76(18) ?
C14 C13 H13 . . 119.1 ?
C12 C13 H13 . . 119.1 ?
C13 C14 C15 . . 119.51(18) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
C14 C15 C16 . . 121.71(18) ?
C14 C15 H15 . . 119.1 ?
C16 C15 H15 . . 119.1 ?
C15 C16 C11 . . 119.03(17) ?
C15 C16 C31 . . 116.06(16) ?
C11 C16 C31 . . 124.88(16) ?
C22 C21 C26 . . 120.25(17) ?
C22 C21 C12 . . 118.23(16) ?
C26 C21 C12 . . 121.04(16) ?
C23 C22 C21 . . 119.08(18) ?
C23 C22 C27 . . 119.49(17) ?
C21 C22 C27 . . 121.37(17) ?
C22 C23 C24 . . 121.68(18) ?
C22 C23 H23 . . 119.2 ?
C24 C23 H23 . . 119.2 ?
C25 C24 C23 . . 117.88(18) ?
C25 C24 C28 . . 120.97(18) ?
C23 C24 C28 . . 121.12(18) ?
C26 C25 C24 . . 122.33(18) ?
C26 C25 H25 . . 118.8 ?
C24 C25 H25 . . 118.8 ?
C25 C26 C21 . . 118.74(17) ?
C25 C26 C29 . . 119.42(17) ?
C21 C26 C29 . . 121.84(17) ?
C22 C27 H27A . . 109.5 ?
C22 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C22 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C24 C28 H28A . . 109.5 ?
C24 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C24 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C26 C29 H29A . . 109.5 ?
C26 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
C26 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
C32 C31 C36 . . 119.08(17) ?
C32 C31 C16 . . 120.01(17) ?
C36 C31 C16 . . 120.49(17) ?
C33 C32 C31 . . 118.81(17) ?
C33 C32 C37 . . 118.66(17) ?
C31 C32 C37 . . 122.37(17) ?
C34 C33 C32 . . 122.37(18) ?
C34 C33 H33 . . 118.8 ?
C32 C33 H33 . . 118.8 ?
C33 C34 C35 . . 117.63(18) ?
C33 C34 C38 . . 121.40(18) ?
C35 C34 C38 . . 120.93(18) ?
C36 C35 C34 . . 122.22(18) ?
C36 C35 H35 . . 118.9 ?
C34 C35 H35 . . 118.9 ?
C35 C36 C31 . . 119.53(17) ?
C35 C36 C39 . . 118.26(18) ?
C31 C36 C39 . . 122.18(18) ?
C32 C37 H37A . . 109.5 ?
C32 C37 H37B . . 109.5 ?
H37A C37 H37B . . 109.5 ?
C32 C37 H37C . . 109.5 ?
H37A C37 H37C . . 109.5 ?
H37B C37 H37C . . 109.5 ?
C34 C38 H38A . . 109.5 ?
C34 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C34 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C36 C39 H39A . . 109.5 ?
C36 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C36 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
C42 C41 C46 . . 112.87(17) ?
C42 C41 B1 . . 128.18(17) ?
C46 C41 B1 . . 118.94(16) ?
F42 C42 C43 . . 114.98(17) ?
F42 C42 C41 . . 120.95(17) ?
C43 C42 C41 . . 124.08(18) ?
F43 C43 C44 . . 119.20(17) ?
F43 C43 C42 . . 120.85(18) ?
C44 C43 C42 . . 119.94(18) ?
F44 C44 C45 . . 121.02(18) ?
F44 C44 C43 . . 120.40(18) ?
C45 C44 C43 . . 118.53(17) ?
F45 C45 C44 . . 119.59(17) ?
F45 C45 C46 . . 120.97(17) ?
C44 C45 C46 . . 119.42(17) ?
F46 C46 C45 . . 115.29(16) ?
F46 C46 C41 . . 119.65(16) ?
C45 C46 C41 . . 125.07(18) ?
C52 C51 C56 . . 112.88(17) ?
C52 C51 B1 . . 127.77(17) ?
C56 C51 B1 . . 119.30(17) ?
F52 C52 C53 . . 114.33(17) ?
F52 C52 C51 . . 121.36(17) ?
C53 C52 C51 . . 124.30(18) ?
F53 C53 C54 . . 119.46(17) ?
F53 C53 C52 . . 120.86(18) ?
C54 C53 C52 . . 119.67(18) ?
F54 C54 C53 . . 119.91(19) ?
F54 C54 C55 . . 121.03(18) ?
C53 C54 C55 . . 119.04(18) ?
F55 C55 C54 . . 119.79(18) ?
F55 C55 C56 . . 121.00(18) ?
C54 C55 C56 . . 119.21(18) ?
F56 C56 C55 . . 115.73(17) ?
F56 C56 C51 . . 119.41(17) ?
C55 C56 C51 . . 124.86(18) ?
C62 C61 C66 . . 118.97(18) ?
C62 C61 C5 . . 118.71(17) ?
C66 C61 C5 . . 122.32(18) ?
C63 C62 C61 . . 120.79(19) ?
C63 C62 H62 . . 119.6 ?
C61 C62 H62 . . 119.6 ?
C64 C63 C62 . . 120.0(2) ?
C64 C63 H63 . . 120.0 ?
C62 C63 H63 . . 120.0 ?
C63 C64 C65 . . 119.8(2) ?
C63 C64 H64 . . 120.1 ?
C65 C64 H64 . . 120.1 ?
C66 C65 C64 . . 120.2(2) ?
C66 C65 H65 . . 119.9 ?
C64 C65 H65 . . 119.9 ?
C65 C66 C61 . . 120.2(2) ?
C65 C66 H66 . . 119.9 ?
C61 C66 H66 . . 119.9 ?
C76 C71 C72 . . 118.76(18) ?
C76 C71 C7 . . 120.30(18) ?
C72 C71 C7 . . 120.66(17) ?
C73 C72 C71 . . 120.61(19) ?
C73 C72 H72 . . 119.7 ?
C71 C72 H72 . . 119.7 ?
C72 C73 C74 . . 120.3(2) ?
C72 C73 H73 . . 119.9 ?
C74 C73 H73 . . 119.9 ?
C75 C74 C73 . . 119.5(2) ?
C75 C74 H74 . . 120.3 ?
C73 C74 H74 . . 120.3 ?
C74 C75 C76 . . 120.5(2) ?
C74 C75 H75 . . 119.7 ?
C76 C75 H75 . . 119.7 ?
C75 C76 C71 . . 120.3(2) ?
C75 C76 H76 . . 119.8 ?
C71 C76 H76 . . 119.8 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 P1 C1 C2 . . . . 14.90(13) ?
C11 P1 C1 C2 . . . . 138.98(12) ?
C5 P1 C1 C2 . . . . -99.37(13) ?
P1 C1 C2 C3 . . . . -36.54(16) ?
P1 C1 C2 B1 . . . . 91.18(16) ?
C1 P1 C4 C3 . . . . 11.38(13) ?
C11 P1 C4 C3 . . . . -106.22(13) ?
C5 P1 C4 C3 . . . . 131.28(12) ?
P1 C4 C3 C2 . . . . -35.60(17) ?
C1 C2 C3 C4 . . . . 47.60(19) ?
B1 C2 C3 C4 . . . . -77.8(2) ?
C3 C2 B1 O1 . . . . 74.8(2) ?
C1 C2 B1 O1 . . . . -46.3(2) ?
C3 C2 B1 C41 . . . . -43.9(2) ?
C1 C2 B1 C41 . . . . -164.98(15) ?
C3 C2 B1 C51 . . . . -160.76(15) ?
C1 C2 B1 C51 . . . . 78.1(2) ?
C2 B1 O1 C7 . . . . 85.7(2) ?
C41 B1 O1 C7 . . . . -156.33(16) ?
C51 B1 O1 C7 . . . . -40.7(2) ?
C4 P1 C5 C6 . . . . -104.02(14) ?
C1 P1 C5 C6 . . . . 3.40(17) ?
C11 P1 C5 C6 . . . . 126.69(13) ?
C4 P1 C5 C61 . . . . 28.92(15) ?
C1 P1 C5 C61 . . . . 136.34(13) ?
C11 P1 C5 C61 . . . . -100.37(14) ?
C61 C5 C6 C7 . . . . -77.2(2) ?
P1 C5 C6 C7 . . . . 53.1(2) ?
C5 C6 C7 O1 . . . . 4.7(3) ?
C5 C6 C7 C71 . . . . 178.40(17) ?
B1 O1 C7 C6 . . . . -117.1(2) ?
B1 O1 C7 C71 . . . . 69.3(2) ?
C4 P1 C11 C12 . . . . 2.58(19) ?
C1 P1 C11 C12 . . . . -107.74(16) ?
C5 P1 C11 C12 . . . . 125.73(16) ?
C4 P1 C11 C16 . . . . -179.40(13) ?
C1 P1 C11 C16 . . . . 70.27(16) ?
C5 P1 C11 C16 . . . . -56.25(16) ?
C16 C11 C12 C13 . . . . 3.6(3) ?
P1 C11 C12 C13 . . . . -178.45(14) ?
C16 C11 C12 C21 . . . . -172.25(17) ?
P1 C11 C12 C21 . . . . 5.7(3) ?
C11 C12 C13 C14 . . . . -2.7(3) ?
C21 C12 C13 C14 . . . . 173.64(17) ?
C12 C13 C14 C15 . . . . 0.2(3) ?
C13 C14 C15 C16 . . . . 1.3(3) ?
C14 C15 C16 C11 . . . . -0.3(3) ?
C14 C15 C16 C31 . . . . -178.33(18) ?
C12 C11 C16 C15 . . . . -2.1(3) ?
P1 C11 C16 C15 . . . . 179.77(14) ?
C12 C11 C16 C31 . . . . 175.72(17) ?
P1 C11 C16 C31 . . . . -2.4(2) ?
C13 C12 C21 C22 . . . . -88.6(2) ?
C11 C12 C21 C22 . . . . 87.4(2) ?
C13 C12 C21 C26 . . . . 83.4(2) ?
C11 C12 C21 C26 . . . . -100.6(2) ?
C26 C21 C22 C23 . . . . 2.1(3) ?
C12 C21 C22 C23 . . . . 174.20(17) ?
C26 C21 C22 C27 . . . . -175.20(17) ?
C12 C21 C22 C27 . . . . -3.1(3) ?
C21 C22 C23 C24 . . . . -1.0(3) ?
C27 C22 C23 C24 . . . . 176.39(18) ?
C22 C23 C24 C25 . . . . 0.0(3) ?
C22 C23 C24 C28 . . . . -177.90(19) ?
C23 C24 C25 C26 . . . . -0.2(3) ?
C28 C24 C25 C26 . . . . 177.70(18) ?
C24 C25 C26 C21 . . . . 1.4(3) ?
C24 C25 C26 C29 . . . . -178.08(18) ?
C22 C21 C26 C25 . . . . -2.3(3) ?
C12 C21 C26 C25 . . . . -174.16(17) ?
C22 C21 C26 C29 . . . . 177.14(17) ?
C12 C21 C26 C29 . . . . 5.3(3) ?
C15 C16 C31 C32 . . . . 91.9(2) ?
C11 C16 C31 C32 . . . . -86.0(2) ?
C15 C16 C31 C36 . . . . -80.7(2) ?
C11 C16 C31 C36 . . . . 101.4(2) ?
C36 C31 C32 C33 . . . . -6.6(3) ?
C16 C31 C32 C33 . . . . -179.27(17) ?
C36 C31 C32 C37 . . . . 168.83(17) ?
C16 C31 C32 C37 . . . . -3.9(3) ?
C31 C32 C33 C34 . . . . 2.4(3) ?
C37 C32 C33 C34 . . . . -173.19(17) ?
C32 C33 C34 C35 . . . . 2.1(3) ?
C32 C33 C34 C38 . . . . 179.86(18) ?
C33 C34 C35 C36 . . . . -2.5(3) ?
C38 C34 C35 C36 . . . . 179.78(18) ?
C34 C35 C36 C31 . . . . -1.7(3) ?
C34 C35 C36 C39 . . . . 176.32(18) ?
C32 C31 C36 C35 . . . . 6.3(3) ?
C16 C31 C36 C35 . . . . 178.95(17) ?
C32 C31 C36 C39 . . . . -171.67(18) ?
C16 C31 C36 C39 . . . . 1.0(3) ?
O1 B1 C41 C42 . . . . -10.4(3) ?
C2 B1 C41 C42 . . . . 108.3(2) ?
C51 B1 C41 C42 . . . . -129.40(19) ?
O1 B1 C41 C46 . . . . 170.53(16) ?
C2 B1 C41 C46 . . . . -70.7(2) ?
C51 B1 C41 C46 . . . . 51.6(2) ?
C46 C41 C42 F42 . . . . 178.06(16) ?
B1 C41 C42 F42 . . . . -1.0(3) ?
C46 C41 C42 C43 . . . . -1.8(3) ?
B1 C41 C42 C43 . . . . 179.10(18) ?
F42 C42 C43 F43 . . . . -2.0(3) ?
C41 C42 C43 F43 . . . . 177.83(17) ?
F42 C42 C43 C44 . . . . 179.38(17) ?
C41 C42 C43 C44 . . . . -0.7(3) ?
F43 C43 C44 F44 . . . . 0.8(3) ?
C42 C43 C44 F44 . . . . 179.44(17) ?
F43 C43 C44 C45 . . . . -176.67(17) ?
C42 C43 C44 C45 . . . . 1.9(3) ?
F44 C44 C45 F45 . . . . 0.4(3) ?
C43 C44 C45 F45 . . . . 177.86(17) ?
F44 C44 C45 C46 . . . . -177.94(17) ?
C43 C44 C45 C46 . . . . -0.4(3) ?
F45 C45 C46 F46 . . . . -0.6(3) ?
C44 C45 C46 F46 . . . . 177.65(16) ?
F45 C45 C46 C41 . . . . 179.28(17) ?
C44 C45 C46 C41 . . . . -2.4(3) ?
C42 C41 C46 F46 . . . . -176.66(16) ?
B1 C41 C46 F46 . . . . 2.5(3) ?
C42 C41 C46 C45 . . . . 3.4(3) ?
B1 C41 C46 C45 . . . . -177.39(18) ?
O1 B1 C51 C52 . . . . 117.8(2) ?
C2 B1 C51 C52 . . . . -5.9(3) ?
C41 B1 C51 C52 . . . . -124.31(19) ?
O1 B1 C51 C56 . . . . -65.1(2) ?
C2 B1 C51 C56 . . . . 171.20(16) ?
C41 B1 C51 C56 . . . . 52.8(2) ?
C56 C51 C52 F52 . . . . -179.59(16) ?
B1 C51 C52 F52 . . . . -2.3(3) ?
C56 C51 C52 C53 . . . . -0.6(3) ?
B1 C51 C52 C53 . . . . 176.72(18) ?
F52 C52 C53 F53 . . . . 1.3(3) ?
C51 C52 C53 F53 . . . . -177.80(17) ?
F52 C52 C53 C54 . . . . -178.77(17) ?
C51 C52 C53 C54 . . . . 2.1(3) ?
F53 C53 C54 F54 . . . . -0.4(3) ?
C52 C53 C54 F54 . . . . 179.68(17) ?
F53 C53 C54 C55 . . . . 178.00(17) ?
C52 C53 C54 C55 . . . . -1.9(3) ?
F54 C54 C55 F55 . . . . -0.6(3) ?
C53 C54 C55 F55 . . . . -178.92(17) ?
F54 C54 C55 C56 . . . . 178.67(18) ?
C53 C54 C55 C56 . . . . 0.3(3) ?
F55 C55 C56 F56 . . . . 0.9(3) ?
C54 C55 C56 F56 . . . . -178.34(17) ?
F55 C55 C56 C51 . . . . -179.43(17) ?
C54 C55 C56 C51 . . . . 1.4(3) ?
C52 C51 C56 F56 . . . . 178.48(16) ?
B1 C51 C56 F56 . . . . 0.9(3) ?
C52 C51 C56 C55 . . . . -1.2(3) ?
B1 C51 C56 C55 . . . . -178.74(18) ?
C6 C5 C61 C62 . . . . -146.41(18) ?
P1 C5 C61 C62 . . . . 82.95(19) ?
C6 C5 C61 C66 . . . . 33.0(3) ?
P1 C5 C61 C66 . . . . -97.63(19) ?
C66 C61 C62 C63 . . . . 0.9(3) ?
C5 C61 C62 C63 . . . . -179.66(17) ?
C61 C62 C63 C64 . . . . -0.8(3) ?
C62 C63 C64 C65 . . . . 0.4(3) ?
C63 C64 C65 C66 . . . . 0.0(3) ?
C64 C65 C66 C61 . . . . 0.1(3) ?
C62 C61 C66 C65 . . . . -0.5(3) ?
C5 C61 C66 C65 . . . . -179.92(18) ?
C6 C7 C71 C76 . . . . -107.7(2) ?
O1 C7 C71 C76 . . . . 66.1(2) ?
C6 C7 C71 C72 . . . . 66.2(3) ?
O1 C7 C71 C72 . . . . -120.0(2) ?
C76 C71 C72 C73 . . . . -1.4(3) ?
C7 C71 C72 C73 . . . . -175.35(18) ?
C71 C72 C73 C74 . . . . 1.1(3) ?
C72 C73 C74 C75 . . . . -0.4(3) ?
C73 C74 C75 C76 . . . . 0.0(4) ?
C74 C75 C76 C71 . . . . -0.3(4) ?
C72 C71 C76 C75 . . . . 1.0(3) ?
C7 C71 C76 C75 . . . . 174.9(2) ?



#=============================================================================
#  end of cif data for "erk9472" (compound 12)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================
####################################################################### 
# 
# 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_erk9479
_database_code_depnum_ccdc_archive 'CCDC 1953119'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-09-12 deposited with the CCDC.	2020-06-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H38 B F10 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         846.56

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.0403(3)
_cell_length_b                   13.4516(3)
_cell_length_c                   13.5382(3)
_cell_angle_alpha                111.4550(10)
_cell_angle_beta                 95.2410(10)
_cell_angle_gamma                97.459(2)
_cell_volume                     2000.43(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4786
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872

_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'Mo rotating anode'
_diffrn_source_type              'Mo rotating anode'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Montel mirror'

_diffrn_measurement_device_type  'rotating anode Nonius FR591'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            17312
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_theta_min         4.08
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15

_refine_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.

The hydrogen at P1 atom was refined freely.
;

_reflns_number_total             6858
_reflns_number_gt                5698
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0734
_refine_ls_wR_factor_gt          0.1814
_refine_ls_wR_factor_ref         0.1987
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_number_reflns         6858
_refine_ls_number_parameters     551
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0884P)²+3.9831P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.494
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;

Collect (Nonius B.V., 1998)
;
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.71219(8) 0.42482(7) 0.24782(7) 0.0275(2) Uani d . . . 1 . .
H H1 0.762(3) 0.520(3) 0.265(3) 0.027(9) Uiso d . . . 1 . .
C C1 0.7635(3) 0.3910(3) 0.3589(3) 0.0280(7) Uani d . . . 1 . .
H H1A 0.7999 0.3261 0.3336 0.034 Uiso calc U . R 1 . .
H H1B 0.8193 0.4521 0.412 0.034 Uiso calc U . R 1 . .
C C2 0.6570(3) 0.3682(3) 0.4090(3) 0.0250(7) Uani d . . . 1 . .
H H2 0.6176 0.2923 0.365 0.03 Uiso calc U . R 1 . .
C C4 0.5679(3) 0.4321(3) 0.2742(3) 0.0331(8) Uani d . . . 1 . .
H H4A 0.5417 0.495 0.2641 0.04 Uiso calc U . R 1 . .
H H4B 0.5151 0.3647 0.2278 0.04 Uiso calc U . R 1 . .
C C3 0.5802(3) 0.4458(3) 0.3934(3) 0.0295(8) Uani d . . . 1 . .
H H3A 0.614 0.5217 0.4401 0.035 Uiso calc U . R 1 . .
H H3B 0.5049 0.4285 0.413 0.035 Uiso calc U . R 1 . .
B B1 0.6900(3) 0.3774(3) 0.5345(3) 0.0269(8) Uani d . . . 1 . .
C C11 0.7382(3) 0.3450(3) 0.1149(3) 0.0253(7) Uani d . . . 1 . .
C C12 0.7949(3) 0.3991(3) 0.0579(3) 0.0277(7) Uani d . . . 1 . .
C C13 0.8176(3) 0.3379(3) -0.0436(3) 0.0340(8) Uani d . . . 1 . .
H H13 0.855 0.3734 -0.0836 0.041 Uiso calc U . R 1 . .
C C14 0.7867(3) 0.2263(3) -0.0870(3) 0.0401(9) Uani d . . . 1 . .
H H14 0.8039 0.1858 -0.1559 0.048 Uiso calc U . R 1 . .
C C15 0.7308(3) 0.1732(3) -0.0307(3) 0.0341(8) Uani d . . . 1 . .
H H15 0.7102 0.0964 -0.0613 0.041 Uiso calc U . R 1 . .
C C16 0.7044(3) 0.2305(3) 0.0697(3) 0.0292(8) Uani d . . . 1 . .
C C21 0.8372(3) 0.5186(3) 0.1023(3) 0.0294(8) Uani d . . . 1 . .
C C22 0.7691(3) 0.5898(3) 0.0847(3) 0.0324(8) Uani d . . . 1 . .
C C23 0.8105(3) 0.7002(3) 0.1295(3) 0.0366(9) Uani d . . . 1 . .
H H23 0.7654 0.7484 0.1165 0.044 Uiso calc U . R 1 . .
C C24 0.9163(4) 0.7429(3) 0.1931(3) 0.0393(9) Uani d . . . 1 . .
C C25 0.9825(3) 0.6710(3) 0.2077(3) 0.0360(8) Uani d . . . 1 . .
H H25 1.0553 0.6991 0.2499 0.043 Uiso calc U . R 1 . .
C C26 0.9462(3) 0.5596(3) 0.1629(3) 0.0296(8) Uani d . . . 1 . .
C C27 0.6527(4) 0.5479(4) 0.0192(4) 0.0498(11) Uani d . . . 1 . .
H H27A 0.6126 0.6088 0.0277 0.075 Uiso calc U . R 1 . .
H H27B 0.6102 0.4965 0.0439 0.075 Uiso calc U . R 1 . .
H H27C 0.6596 0.5113 -0.0567 0.075 Uiso calc U . R 1 . .
C C28 0.9572(5) 0.8639(4) 0.2436(4) 0.0560(12) Uani d . . . 1 . .
H H28A 1.029 0.8796 0.2913 0.084 Uiso calc U . R 1 . .
H H28B 0.9006 0.8989 0.2851 0.084 Uiso calc U . R 1 . .
H H28C 0.9685 0.892 0.1872 0.084 Uiso calc U . R 1 . .
C C29 1.0215(3) 0.4825(3) 0.1758(3) 0.0415(9) Uani d . . . 1 . .
H H29A 1.0927 0.5241 0.2222 0.062 Uiso calc U . R 1 . .
H H29B 1.0378 0.4372 0.1053 0.062 Uiso calc U . R 1 . .
H H29C 0.9831 0.4362 0.2084 0.062 Uiso calc U . R 1 . .
C C31 0.6405(3) 0.1703(3) 0.1261(3) 0.0291(7) Uani d . . . 1 . .
C C32 0.5213(3) 0.1573(3) 0.1133(3) 0.0317(8) Uani d . . . 1 . .
C C33 0.4624(3) 0.1041(3) 0.1686(3) 0.0355(8) Uani d . . . 1 . .
H H33 0.3825 0.0993 0.1637 0.043 Uiso calc U . R 1 . .
C C34 0.5178(3) 0.0579(3) 0.2308(3) 0.0353(8) Uani d . . . 1 . .
C C35 0.6339(3) 0.0649(3) 0.2364(3) 0.0346(8) Uani d . . . 1 . .
H H35 0.6718 0.0312 0.2768 0.041 Uiso calc U . R 1 . .
C C36 0.6973(3) 0.1196(3) 0.1848(3) 0.0313(8) Uani d . . . 1 . .
C C37 0.4567(3) 0.1961(3) 0.0373(3) 0.0391(9) Uani d . . . 1 . .
H H37A 0.451 0.1436 -0.0365 0.059 Uiso calc U . R 1 . .
H H37B 0.4967 0.2668 0.0433 0.059 Uiso calc U . R 1 . .
H H37C 0.3805 0.203 0.0558 0.059 Uiso calc U . R 1 . .
C C38 0.4512(4) 0.0010(4) 0.2910(4) 0.0497(11) Uani d . . . 1 . .
H H38A 0.4307 -0.0768 0.2468 0.074 Uiso calc U . R 1 . .
H H38B 0.3823 0.0315 0.3066 0.074 Uiso calc U . R 1 . .
H H38C 0.4979 0.0114 0.3585 0.074 Uiso calc U . R 1 . .
C C39 0.8236(3) 0.1221(3) 0.1913(3) 0.0416(9) Uani d . . . 1 . .
H H39A 0.8526 0.1135 0.2572 0.062 Uiso calc U . R 1 . .
H H39B 0.8608 0.1917 0.1921 0.062 Uiso calc U . R 1 . .
H H39C 0.8392 0.0628 0.1289 0.062 Uiso calc U . R 1 . .
C C41 0.5848(3) 0.3265(3) 0.5824(3) 0.0272(7) Uani d . . . 1 . .
F F42 0.44440(18) 0.26137(19) 0.42630(17) 0.0408(5) Uani d . . . 1 . .
C C42 0.4766(3) 0.2728(3) 0.5285(3) 0.0296(8) Uani d . . . 1 . .
F F43 0.29444(19) 0.1731(2) 0.5135(2) 0.0552(7) Uani d . . . 1 . .
C C43 0.3962(3) 0.2267(3) 0.5720(3) 0.0359(8) Uani d . . . 1 . .
F F44 0.3442(2) 0.1822(2) 0.7175(2) 0.0515(6) Uani d . . . 1 . .
C C44 0.4197(3) 0.2303(3) 0.6743(3) 0.0369(9) Uani d . . . 1 . .
F F45 0.5496(2) 0.2889(2) 0.83405(18) 0.0495(6) Uani d . . . 1 . .
C C45 0.5248(3) 0.2847(3) 0.7332(3) 0.0360(9) Uani d . . . 1 . .
F F46 0.70573(19) 0.37602(19) 0.74778(17) 0.0414(5) Uani d . . . 1 . .
C C46 0.6028(3) 0.3289(3) 0.6861(3) 0.0303(8) Uani d . . . 1 . .
C C51 0.7937(3) 0.3062(3) 0.5313(3) 0.0255(7) Uani d . . . 1 . .
F F52 0.66686(17) 0.14047(16) 0.48901(18) 0.0387(5) Uani d . . . 1 . .
C C52 0.7740(3) 0.1949(3) 0.5048(3) 0.0294(8) Uani d . . . 1 . .
F F53 0.8288(2) 0.02361(18) 0.4613(2) 0.0543(7) Uani d . . . 1 . .
C C53 0.8571(3) 0.1307(3) 0.4888(3) 0.0357(8) Uani d . . . 1 . .
F F54 1.0502(2) 0.1173(2) 0.4869(2) 0.0541(7) Uani d . . . 1 . .
C C54 0.9690(3) 0.1780(3) 0.5015(3) 0.0352(8) Uani d . . . 1 . .
F F55 1.10367(18) 0.33639(19) 0.5460(2) 0.0460(6) Uani d . . . 1 . .
C C55 0.9944(3) 0.2885(3) 0.5307(3) 0.0346(8) Uani d . . . 1 . .
F F56 0.94362(17) 0.45631(17) 0.56941(18) 0.0370(5) Uani d . . . 1 . .
C C56 0.9088(3) 0.3490(3) 0.5442(3) 0.0284(7) Uani d . . . 1 . .
C C5 0.7288(3) 0.5009(3) 0.6119(3) 0.0274(7) Uani d . . . 1 . .
C C6 0.7570(3) 0.5952(3) 0.6717(3) 0.0318(8) Uani d . . . 1 . .
C C61 0.7973(3) 0.7061(3) 0.7432(3) 0.0306(8) Uani d . . . 1 . .
C C62 0.8159(3) 0.7874(3) 0.7024(3) 0.0392(9) Uani d . . . 1 . .
H H62 0.7998 0.7693 0.6272 0.047 Uiso calc U . R 1 . .
C C63 0.8572(4) 0.8933(3) 0.7695(4) 0.0452(10) Uani d . . . 1 . .
H H63 0.8698 0.9473 0.7401 0.054 Uiso calc U . R 1 . .
C C64 0.8805(3) 0.9224(3) 0.8796(4) 0.0460(10) Uani d . . . 1 . .
H H64 0.9079 0.9959 0.9258 0.055 Uiso calc U . R 1 . .
C C65 0.8632(4) 0.8422(4) 0.9214(3) 0.0451(10) Uani d . . . 1 . .
H H65 0.8799 0.8608 0.9966 0.054 Uiso calc U . R 1 . .
C C66 0.8218(3) 0.7354(3) 0.8540(3) 0.0375(9) Uani d . . . 1 . .
H H66 0.8099 0.6814 0.8835 0.045 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C1 . 1.804(3) ?
P1 C11 . 1.807(3) ?
P1 C4 . 1.813(4) ?
P1 H1 . 1.27(4) ?
C1 C2 . 1.551(5) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.538(5) ?
C2 B1 . 1.665(5) ?
C2 H2 . 1.0 ?
C4 C3 . 1.547(5) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
B1 C5 . 1.585(5) ?
B1 C41 . 1.657(5) ?
B1 C51 . 1.664(5) ?
C11 C12 . 1.404(5) ?
C11 C16 . 1.420(5) ?
C12 C13 . 1.393(5) ?
C12 C21 . 1.492(5) ?
C13 C14 . 1.381(6) ?
C13 H13 . 0.95 ?
C14 C15 . 1.382(6) ?
C14 H14 . 0.95 ?
C15 C16 . 1.386(5) ?
C15 H15 . 0.95 ?
C16 C31 . 1.492(5) ?
C21 C22 . 1.408(5) ?
C21 C26 . 1.409(5) ?
C22 C23 . 1.384(5) ?
C22 C27 . 1.506(5) ?
C23 C24 . 1.393(6) ?
C23 H23 . 0.95 ?
C24 C25 . 1.385(6) ?
C24 C28 . 1.509(6) ?
C25 C26 . 1.386(5) ?
C25 H25 . 0.95 ?
C26 C29 . 1.509(5) ?
C27 H27A . 0.98 ?
C27 H27B . 0.98 ?
C27 H27C . 0.98 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C29 H29A . 0.98 ?
C29 H29B . 0.98 ?
C29 H29C . 0.98 ?
C31 C36 . 1.408(5) ?
C31 C32 . 1.411(5) ?
C32 C33 . 1.390(5) ?
C32 C37 . 1.512(5) ?
C33 C34 . 1.389(6) ?
C33 H33 . 0.95 ?
C34 C35 . 1.382(6) ?
C34 C38 . 1.520(5) ?
C35 C36 . 1.392(5) ?
C35 H35 . 0.95 ?
C36 C39 . 1.510(5) ?
C37 H37A . 0.98 ?
C37 H37B . 0.98 ?
C37 H37C . 0.98 ?
C38 H38A . 0.98 ?
C38 H38B . 0.98 ?
C38 H38C . 0.98 ?
C39 H39A . 0.98 ?
C39 H39B . 0.98 ?
C39 H39C . 0.98 ?
C41 C46 . 1.387(5) ?
C41 C42 . 1.396(5) ?
F42 C42 . 1.349(4) ?
C42 C43 . 1.373(5) ?
F43 C43 . 1.351(4) ?
C43 C44 . 1.370(6) ?
F44 C44 . 1.345(4) ?
C44 C45 . 1.385(6) ?
F45 C45 . 1.349(4) ?
C45 C46 . 1.374(5) ?
F46 C46 . 1.362(4) ?
C51 C52 . 1.387(5) ?
C51 C56 . 1.399(5) ?
F52 C52 . 1.355(4) ?
C52 C53 . 1.385(5) ?
F53 C53 . 1.337(4) ?
C53 C54 . 1.380(5) ?
F54 C54 . 1.336(4) ?
C54 C55 . 1.374(5) ?
F55 C55 . 1.350(4) ?
C55 C56 . 1.379(5) ?
F56 C56 . 1.353(4) ?
C5 C6 . 1.211(5) ?
C6 C61 . 1.438(5) ?
C61 C66 . 1.396(5) ?
C61 C62 . 1.398(5) ?
C62 C63 . 1.374(6) ?
C62 H62 . 0.95 ?
C63 C64 . 1.386(6) ?
C63 H63 . 0.95 ?
C64 C65 . 1.392(7) ?
C64 H64 . 0.95 ?
C65 C66 . 1.384(6) ?
C65 H65 . 0.95 ?
C66 H66 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 P1 C11 . . 118.79(16) ?
C1 P1 C4 . . 98.20(16) ?
C11 P1 C4 . . 119.82(16) ?
C1 P1 H1 . . 107.4(16) ?
C11 P1 H1 . . 103.7(16) ?
C4 P1 H1 . . 108.3(16) ?
C2 C1 P1 . . 105.2(2) ?
C2 C1 H1A . . 110.7 ?
P1 C1 H1A . . 110.7 ?
C2 C1 H1B . . 110.7 ?
P1 C1 H1B . . 110.7 ?
H1A C1 H1B . . 108.8 ?
C3 C2 C1 . . 104.8(3) ?
C3 C2 B1 . . 116.0(3) ?
C1 C2 B1 . . 112.2(3) ?
C3 C2 H2 . . 107.8 ?
C1 C2 H2 . . 107.8 ?
B1 C2 H2 . . 107.8 ?
C3 C4 P1 . . 101.2(2) ?
C3 C4 H4A . . 111.5 ?
P1 C4 H4A . . 111.5 ?
C3 C4 H4B . . 111.5 ?
P1 C4 H4B . . 111.5 ?
H4A C4 H4B . . 109.3 ?
C2 C3 C4 . . 108.2(3) ?
C2 C3 H3A . . 110.1 ?
C4 C3 H3A . . 110.1 ?
C2 C3 H3B . . 110.1 ?
C4 C3 H3B . . 110.1 ?
H3A C3 H3B . . 108.4 ?
C5 B1 C41 . . 107.1(3) ?
C5 B1 C51 . . 112.0(3) ?
C41 B1 C51 . . 108.2(3) ?
C5 B1 C2 . . 109.7(3) ?
C41 B1 C2 . . 114.4(3) ?
C51 B1 C2 . . 105.5(3) ?
C12 C11 C16 . . 120.6(3) ?
C12 C11 P1 . . 118.2(3) ?
C16 C11 P1 . . 121.2(3) ?
C13 C12 C11 . . 118.5(3) ?
C13 C12 C21 . . 118.0(3) ?
C11 C12 C21 . . 123.4(3) ?
C14 C13 C12 . . 121.1(3) ?
C14 C13 H13 . . 119.5 ?
C12 C13 H13 . . 119.5 ?
C13 C14 C15 . . 120.3(3) ?
C13 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
C14 C15 C16 . . 120.9(3) ?
C14 C15 H15 . . 119.5 ?
C16 C15 H15 . . 119.5 ?
C15 C16 C11 . . 118.6(3) ?
C15 C16 C31 . . 119.1(3) ?
C11 C16 C31 . . 122.3(3) ?
C22 C21 C26 . . 120.1(3) ?
C22 C21 C12 . . 120.7(3) ?
C26 C21 C12 . . 119.2(3) ?
C23 C22 C21 . . 118.8(3) ?
C23 C22 C27 . . 120.0(3) ?
C21 C22 C27 . . 121.2(3) ?
C22 C23 C24 . . 122.0(4) ?
C22 C23 H23 . . 119.0 ?
C24 C23 H23 . . 119.0 ?
C25 C24 C23 . . 118.1(4) ?
C25 C24 C28 . . 121.3(4) ?
C23 C24 C28 . . 120.6(4) ?
C24 C25 C26 . . 122.3(4) ?
C24 C25 H25 . . 118.8 ?
C26 C25 H25 . . 118.8 ?
C25 C26 C21 . . 118.6(3) ?
C25 C26 C29 . . 121.5(3) ?
C21 C26 C29 . . 119.9(3) ?
C22 C27 H27A . . 109.5 ?
C22 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C22 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C24 C28 H28A . . 109.5 ?
C24 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C24 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C26 C29 H29A . . 109.5 ?
C26 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
C26 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
C36 C31 C32 . . 119.9(3) ?
C36 C31 C16 . . 120.7(3) ?
C32 C31 C16 . . 119.3(3) ?
C33 C32 C31 . . 119.1(3) ?
C33 C32 C37 . . 119.7(3) ?
C31 C32 C37 . . 121.2(3) ?
C34 C33 C32 . . 121.5(4) ?
C34 C33 H33 . . 119.3 ?
C32 C33 H33 . . 119.3 ?
C35 C34 C33 . . 118.6(3) ?
C35 C34 C38 . . 121.1(4) ?
C33 C34 C38 . . 120.3(4) ?
C34 C35 C36 . . 122.3(4) ?
C34 C35 H35 . . 118.9 ?
C36 C35 H35 . . 118.9 ?
C35 C36 C31 . . 118.4(3) ?
C35 C36 C39 . . 120.0(3) ?
C31 C36 C39 . . 121.6(3) ?
C32 C37 H37A . . 109.5 ?
C32 C37 H37B . . 109.5 ?
H37A C37 H37B . . 109.5 ?
C32 C37 H37C . . 109.5 ?
H37A C37 H37C . . 109.5 ?
H37B C37 H37C . . 109.5 ?
C34 C38 H38A . . 109.5 ?
C34 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C34 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C36 C39 H39A . . 109.5 ?
C36 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C36 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
C46 C41 C42 . . 112.6(3) ?
C46 C41 B1 . . 119.5(3) ?
C42 C41 B1 . . 127.8(3) ?
F42 C42 C43 . . 114.8(3) ?
F42 C42 C41 . . 120.9(3) ?
C43 C42 C41 . . 124.3(3) ?
F43 C43 C44 . . 118.7(3) ?
F43 C43 C42 . . 120.8(3) ?
C44 C43 C42 . . 120.4(3) ?
F44 C44 C43 . . 121.7(4) ?
F44 C44 C45 . . 120.0(4) ?
C43 C44 C45 . . 118.2(3) ?
F45 C45 C46 . . 121.6(3) ?
F45 C45 C44 . . 119.1(3) ?
C46 C45 C44 . . 119.2(3) ?
F46 C46 C45 . . 115.4(3) ?
F46 C46 C41 . . 119.4(3) ?
C45 C46 C41 . . 125.2(3) ?
C52 C51 C56 . . 112.6(3) ?
C52 C51 B1 . . 123.0(3) ?
C56 C51 B1 . . 124.1(3) ?
F52 C52 C53 . . 115.0(3) ?
F52 C52 C51 . . 120.2(3) ?
C53 C52 C51 . . 124.8(3) ?
F53 C53 C54 . . 120.3(3) ?
F53 C53 C52 . . 120.1(3) ?
C54 C53 C52 . . 119.7(3) ?
F54 C54 C55 . . 121.2(3) ?
F54 C54 C53 . . 120.4(3) ?
C55 C54 C53 . . 118.3(3) ?
F55 C55 C54 . . 119.2(3) ?
F55 C55 C56 . . 120.8(3) ?
C54 C55 C56 . . 120.1(3) ?
F56 C56 C55 . . 114.8(3) ?
F56 C56 C51 . . 120.7(3) ?
C55 C56 C51 . . 124.5(3) ?
C6 C5 B1 . . 179.1(4) ?
C5 C6 C61 . . 176.6(4) ?
C66 C61 C62 . . 118.1(3) ?
C66 C61 C6 . . 121.6(3) ?
C62 C61 C6 . . 120.3(3) ?
C63 C62 C61 . . 120.9(4) ?
C63 C62 H62 . . 119.5 ?
C61 C62 H62 . . 119.5 ?
C62 C63 C64 . . 120.8(4) ?
C62 C63 H63 . . 119.6 ?
C64 C63 H63 . . 119.6 ?
C63 C64 C65 . . 119.0(4) ?
C63 C64 H64 . . 120.5 ?
C65 C64 H64 . . 120.5 ?
C66 C65 C64 . . 120.4(4) ?
C66 C65 H65 . . 119.8 ?
C64 C65 H65 . . 119.8 ?
C65 C66 C61 . . 120.8(4) ?
C65 C66 H66 . . 119.6 ?
C61 C66 H66 . . 119.6 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 P1 C1 C2 . . . . -122.4(2) ?
C4 P1 C1 C2 . . . . 8.3(3) ?
P1 C1 C2 C3 . . . . -33.5(3) ?
P1 C1 C2 B1 . . . . -160.2(2) ?
C1 P1 C4 C3 . . . . 18.9(3) ?
C11 P1 C4 C3 . . . . 149.0(2) ?
C1 C2 C3 C4 . . . . 50.8(4) ?
B1 C2 C3 C4 . . . . 175.2(3) ?
P1 C4 C3 C2 . . . . -42.4(3) ?
C3 C2 B1 C5 . . . . -47.2(4) ?
C1 C2 B1 C5 . . . . 73.3(3) ?
C3 C2 B1 C41 . . . . 73.2(4) ?
C1 C2 B1 C41 . . . . -166.3(3) ?
C3 C2 B1 C51 . . . . -168.0(3) ?
C1 C2 B1 C51 . . . . -47.5(3) ?
C1 P1 C11 C12 . . . . -124.0(3) ?
C4 P1 C11 C12 . . . . 115.9(3) ?
C1 P1 C11 C16 . . . . 54.9(3) ?
C4 P1 C11 C16 . . . . -65.3(3) ?
C16 C11 C12 C13 . . . . -0.3(5) ?
P1 C11 C12 C13 . . . . 178.5(3) ?
C16 C11 C12 C21 . . . . -177.3(3) ?
P1 C11 C12 C21 . . . . 1.6(4) ?
C11 C12 C13 C14 . . . . -0.9(5) ?
C21 C12 C13 C14 . . . . 176.3(3) ?
C12 C13 C14 C15 . . . . 0.9(6) ?
C13 C14 C15 C16 . . . . 0.2(6) ?
C14 C15 C16 C11 . . . . -1.4(5) ?
C14 C15 C16 C31 . . . . 177.9(3) ?
C12 C11 C16 C15 . . . . 1.5(5) ?
P1 C11 C16 C15 . . . . -177.4(3) ?
C12 C11 C16 C31 . . . . -177.9(3) ?
P1 C11 C16 C31 . . . . 3.3(5) ?
C13 C12 C21 C22 . . . . 91.0(4) ?
C11 C12 C21 C22 . . . . -92.1(4) ?
C13 C12 C21 C26 . . . . -89.4(4) ?
C11 C12 C21 C26 . . . . 87.6(4) ?
C26 C21 C22 C23 . . . . -1.2(5) ?
C12 C21 C22 C23 . . . . 178.5(3) ?
C26 C21 C22 C27 . . . . 179.3(4) ?
C12 C21 C22 C27 . . . . -1.0(5) ?
C21 C22 C23 C24 . . . . -1.3(6) ?
C27 C22 C23 C24 . . . . 178.2(4) ?
C22 C23 C24 C25 . . . . 2.4(6) ?
C22 C23 C24 C28 . . . . -178.0(4) ?
C23 C24 C25 C26 . . . . -1.0(6) ?
C28 C24 C25 C26 . . . . 179.4(4) ?
C24 C25 C26 C21 . . . . -1.3(5) ?
C24 C25 C26 C29 . . . . 177.4(4) ?
C22 C21 C26 C25 . . . . 2.5(5) ?
C12 C21 C26 C25 . . . . -177.2(3) ?
C22 C21 C26 C29 . . . . -176.3(3) ?
C12 C21 C26 C29 . . . . 4.1(5) ?
C15 C16 C31 C36 . . . . 82.6(4) ?
C11 C16 C31 C36 . . . . -98.1(4) ?
C15 C16 C31 C32 . . . . -92.6(4) ?
C11 C16 C31 C32 . . . . 86.8(4) ?
C36 C31 C32 C33 . . . . 6.8(5) ?
C16 C31 C32 C33 . . . . -178.0(3) ?
C36 C31 C32 C37 . . . . -170.7(3) ?
C16 C31 C32 C37 . . . . 4.5(5) ?
C31 C32 C33 C34 . . . . -3.9(5) ?
C37 C32 C33 C34 . . . . 173.6(3) ?
C32 C33 C34 C35 . . . . -0.5(5) ?
C32 C33 C34 C38 . . . . 179.5(4) ?
C33 C34 C35 C36 . . . . 2.2(5) ?
C38 C34 C35 C36 . . . . -177.9(4) ?
C34 C35 C36 C31 . . . . 0.7(5) ?
C34 C35 C36 C39 . . . . -178.4(3) ?
C32 C31 C36 C35 . . . . -5.2(5) ?
C16 C31 C36 C35 . . . . 179.7(3) ?
C32 C31 C36 C39 . . . . 173.9(3) ?
C16 C31 C36 C39 . . . . -1.3(5) ?
C5 B1 C41 C46 . . . . -58.7(4) ?
C51 B1 C41 C46 . . . . 62.2(4) ?
C2 B1 C41 C46 . . . . 179.5(3) ?
C5 B1 C41 C42 . . . . 125.7(4) ?
C51 B1 C41 C42 . . . . -113.4(4) ?
C2 B1 C41 C42 . . . . 3.9(5) ?
C46 C41 C42 F42 . . . . -179.2(3) ?
B1 C41 C42 F42 . . . . -3.4(5) ?
C46 C41 C42 C43 . . . . -0.2(5) ?
B1 C41 C42 C43 . . . . 175.7(3) ?
F42 C42 C43 F43 . . . . 1.2(5) ?
C41 C42 C43 F43 . . . . -177.9(3) ?
F42 C42 C43 C44 . . . . 178.2(3) ?
C41 C42 C43 C44 . . . . -0.8(6) ?
F43 C43 C44 F44 . . . . -0.2(6) ?
C42 C43 C44 F44 . . . . -177.3(3) ?
F43 C43 C44 C45 . . . . 179.4(3) ?
C42 C43 C44 C45 . . . . 2.3(6) ?
F44 C44 C45 F45 . . . . -0.3(6) ?
C43 C44 C45 F45 . . . . -179.9(3) ?
F44 C44 C45 C46 . . . . 176.9(3) ?
C43 C44 C45 C46 . . . . -2.7(6) ?
F45 C45 C46 F46 . . . . 0.4(5) ?
C44 C45 C46 F46 . . . . -176.8(3) ?
F45 C45 C46 C41 . . . . 178.9(3) ?
C44 C45 C46 C41 . . . . 1.7(6) ?
C42 C41 C46 F46 . . . . 178.2(3) ?
B1 C41 C46 F46 . . . . 1.9(5) ?
C42 C41 C46 C45 . . . . -0.2(5) ?
B1 C41 C46 C45 . . . . -176.5(3) ?
C5 B1 C51 C52 . . . . 155.3(3) ?
C41 B1 C51 C52 . . . . 37.5(4) ?
C2 B1 C51 C52 . . . . -85.4(4) ?
C5 B1 C51 C56 . . . . -31.5(5) ?
C41 B1 C51 C56 . . . . -149.3(3) ?
C2 B1 C51 C56 . . . . 87.8(4) ?
C56 C51 C52 F52 . . . . -179.8(3) ?
B1 C51 C52 F52 . . . . -5.8(5) ?
C56 C51 C52 C53 . . . . -2.0(5) ?
B1 C51 C52 C53 . . . . 171.9(3) ?
F52 C52 C53 F53 . . . . -0.9(5) ?
C51 C52 C53 F53 . . . . -178.7(3) ?
F52 C52 C53 C54 . . . . 179.2(3) ?
C51 C52 C53 C54 . . . . 1.4(6) ?
F53 C53 C54 F54 . . . . -0.2(6) ?
C52 C53 C54 F54 . . . . 179.6(3) ?
F53 C53 C54 C55 . . . . -179.4(4) ?
C52 C53 C54 C55 . . . . 0.5(6) ?
F54 C54 C55 F55 . . . . -0.7(6) ?
C53 C54 C55 F55 . . . . 178.4(3) ?
F54 C54 C55 C56 . . . . 179.4(3) ?
C53 C54 C55 C56 . . . . -1.5(6) ?
F55 C55 C56 F56 . . . . 2.3(5) ?
C54 C55 C56 F56 . . . . -177.8(3) ?
F55 C55 C56 C51 . . . . -179.1(3) ?
C54 C55 C56 C51 . . . . 0.8(6) ?
C52 C51 C56 F56 . . . . 179.5(3) ?
B1 C51 C56 F56 . . . . 5.6(5) ?
C52 C51 C56 C55 . . . . 0.9(5) ?
B1 C51 C56 C55 . . . . -172.9(3) ?
C66 C61 C62 C63 . . . . 0.0(6) ?
C6 C61 C62 C63 . . . . -178.3(4) ?
C61 C62 C63 C64 . . . . -0.5(6) ?
C62 C63 C64 C65 . . . . 1.0(6) ?
C63 C64 C65 C66 . . . . -0.9(6) ?
C64 C65 C66 C61 . . . . 0.3(6) ?
C62 C61 C66 C65 . . . . 0.1(6) ?
C6 C61 C66 C65 . . . . 178.4(4) ?


