# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_erk7611
_database_code_depnum_ccdc_archive 'CCDC 1419592'
_audit_update_record             
;
2015-08-19 deposited with the CCDC.
2015-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H29 O P'
_chemical_formula_weight         340.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   15.6981(4)
_cell_length_b                   7.4997(2)
_cell_length_c                   16.6619(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.155(1)
_cell_angle_gamma                90.00
_cell_volume                     1958.65(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4604
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9841
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16993
_diffrn_reflns_av_R_equivalents  0.071
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.41
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3359
_reflns_number_gt                2313
_reflns_threshold_expression     >2sigma(I)

_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0326P)²+2.3251P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3359
_refine_ls_number_parameters     271
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.1669
_refine_ls_wR_factor_gt          0.1440
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.23904(7) 0.18787(15) 0.00073(6) 0.0571(3) Uani 1 1 d D . .
C1 C 0.2727(11) 0.3944(17) -0.0419(7) 0.099(5) Uani 0.599(7) 1 d PDU A 1
H1 H 0.2929 0.4832 -0.0058 0.118 Uiso 0.599(7) 1 calc PR A 1
C2 C 0.2719(7) 0.4307(13) -0.1142(5) 0.068(3) Uani 0.599(7) 1 d PDU A 1
H2 H 0.2574 0.3341 -0.1482 0.082 Uiso 0.599(7) 1 calc PR A 1
C3 C 0.2894(5) 0.5964(9) -0.1569(4) 0.066(2) Uani 0.599(7) 1 d PDU A 1
H3A H 0.2489 0.6035 -0.2037 0.079 Uiso 0.599(7) 1 calc PR A 1
H3B H 0.3466 0.5860 -0.1774 0.079 Uiso 0.599(7) 1 calc PR A 1
C4 C 0.2857(6) 0.7663(13) -0.1136(6) 0.087(3) Uani 0.599(7) 1 d PDU A 1
H4A H 0.3016 0.7483 -0.0565 0.105 Uiso 0.599(7) 1 calc PR A 1
H4B H 0.3256 0.8518 -0.1354 0.105 Uiso 0.599(7) 1 calc PR A 1
O1 O 0.1988(4) 0.8344(9) -0.1234(4) 0.098(2) Uani 0.599(7) 1 d PDU A 1
H1A H 0.1974 0.9382 -0.1062 0.147 Uiso 0.599(7) 1 calc PR A 1
C1A C 0.2794(13) 0.4134(15) -0.0204(9) 0.052(3) Uani 0.401(7) 1 d PDU A 2
H1A1 H 0.3019 0.4792 0.0239 0.062 Uiso 0.401(7) 1 calc PR A 2
C2A C 0.2798(13) 0.4866(17) -0.0871(8) 0.077(5) Uani 0.401(7) 1 d PDU A 2
H2A H 0.2510 0.4228 -0.1289 0.092 Uiso 0.401(7) 1 calc PR A 2
C3A C 0.3185(8) 0.6604(18) -0.1130(9) 0.073(4) Uani 0.401(7) 1 d PDU A 2
H3A1 H 0.3373 0.7308 -0.0658 0.088 Uiso 0.401(7) 1 calc PR A 2
H3A2 H 0.3681 0.6370 -0.1447 0.088 Uiso 0.401(7) 1 calc PR A 2
C4A C 0.2528(10) 0.7598(19) -0.1622(10) 0.107(5) Uani 0.401(7) 1 d PDU A 2
H4A1 H 0.2510 0.7241 -0.2188 0.128 Uiso 0.401(7) 1 calc PR A 2
H4A2 H 0.1960 0.7479 -0.1413 0.128 Uiso 0.401(7) 1 calc PR A 2
O1A O 0.2852(7) 0.9252(12) -0.1508(5) 0.104(4) Uani 0.401(7) 1 d PDU A 2
H1A2 H 0.3358 0.9264 -0.1630 0.156 Uiso 0.401(7) 1 calc PR A 2
C11 C 0.1612(2) 0.2650(5) 0.0712(2) 0.0511(9) Uani 1 1 d . A .
C12 C 0.1808(2) 0.3224(5) 0.1505(2) 0.0527(9) Uani 1 1 d . . .
C13 C 0.1153(3) 0.3730(5) 0.1982(2) 0.0614(10) Uani 1 1 d . A .
H13 H 0.1293 0.4115 0.2510 0.074 Uiso 1 1 calc R . .
C14 C 0.0307(3) 0.3696(5) 0.1718(3) 0.0669(11) Uani 1 1 d . . .
C15 C 0.0120(3) 0.3173(5) 0.0931(3) 0.0672(11) Uani 1 1 d . A .
H15 H -0.0452 0.3164 0.0734 0.081 Uiso 1 1 calc R . .
C16 C 0.0750(2) 0.2657(5) 0.0421(2) 0.0575(10) Uani 1 1 d . . .
C17 C 0.2708(2) 0.3314(6) 0.1869(2) 0.0691(11) Uani 1 1 d . A .
H17A H 0.2727 0.4097 0.2333 0.104 Uiso 1 1 calc R . .
H17B H 0.3083 0.3772 0.1474 0.104 Uiso 1 1 calc R . .
H17C H 0.2894 0.2129 0.2034 0.104 Uiso 1 1 calc R . .
C18 C -0.0389(3) 0.4192(7) 0.2263(3) 0.0927(15) Uani 1 1 d . A .
H18A H -0.0786 0.4999 0.1983 0.139 Uiso 1 1 calc R . .
H18B H -0.0140 0.4772 0.2740 0.139 Uiso 1 1 calc R . .
H18C H -0.0688 0.3124 0.2416 0.139 Uiso 1 1 calc R . .
C19 C 0.0483(3) 0.2114(6) -0.0428(2) 0.0767(13) Uani 1 1 d . A .
H19A H 0.0582 0.0847 -0.0494 0.115 Uiso 1 1 calc R . .
H19B H 0.0814 0.2776 -0.0802 0.115 Uiso 1 1 calc R . .
H19C H -0.0119 0.2369 -0.0533 0.115 Uiso 1 1 calc R . .
C21 C 0.3235(2) 0.0718(5) 0.06161(19) 0.0500(9) Uani 1 1 d . A .
C22 C 0.2969(2) -0.0872(5) 0.0983(2) 0.0533(9) Uani 1 1 d . . .
C23 C 0.3571(3) -0.1914(5) 0.1415(2) 0.0621(10) Uani 1 1 d . A .
H23 H 0.3387 -0.2953 0.1668 0.075 Uiso 1 1 calc R . .
C24 C 0.4426(3) -0.1483(6) 0.1486(2) 0.0659(11) Uani 1 1 d . . .
C25 C 0.4671(3) 0.0049(6) 0.1107(2) 0.0639(11) Uani 1 1 d . A .
H25 H 0.5253 0.0355 0.1140 0.077 Uiso 1 1 calc R . .
C26 C 0.4105(2) 0.1168(5) 0.0679(2) 0.0574(10) Uani 1 1 d . . .
C27 C 0.2047(3) -0.1483(5) 0.0943(2) 0.0666(11) Uani 1 1 d . A .
H27A H 0.1722 -0.0749 0.1296 0.100 Uiso 1 1 calc R . .
H27B H 0.2019 -0.2718 0.1111 0.100 Uiso 1 1 calc R . .
H27C H 0.1809 -0.1371 0.0395 0.100 Uiso 1 1 calc R . .
C28 C 0.5056(3) -0.2654(7) 0.1963(3) 0.1027(18) Uani 1 1 d . A .
H28A H 0.4946 -0.3895 0.1830 0.154 Uiso 1 1 calc R . .
H28B H 0.4993 -0.2470 0.2533 0.154 Uiso 1 1 calc R . .
H28C H 0.5632 -0.2346 0.1831 0.154 Uiso 1 1 calc R . .
C29 C 0.4479(3) 0.2844(6) 0.0336(3) 0.0757(12) Uani 1 1 d . A .
H29A H 0.5095 0.2828 0.0430 0.114 Uiso 1 1 calc R . .
H29B H 0.4247 0.3879 0.0597 0.114 Uiso 1 1 calc R . .
H29C H 0.4336 0.2900 -0.0237 0.114 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.796(10) . ?
P1 C11 1.834(4) . ?
P1 C21 1.843(4) . ?
P1 C1A 1.846(11) . ?
C1 C2 1.235(11) . ?
C1 H1 0.9400 . ?
C2 C3 1.465(9) . ?
C2 H2 0.9400 . ?
C3 C4 1.467(9) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 O1 1.457(10) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
O1 H1A 0.8300 . ?
C1A C2A 1.241(13) . ?
C1A H1A1 0.9400 . ?
C2A C3A 1.511(12) . ?
C2A H2A 0.9400 . ?
C3A C4A 1.482(13) . ?
C3A H3A1 0.9800 . ?
C3A H3A2 0.9800 . ?
C4A O1A 1.350(14) . ?
C4A H4A1 0.9800 . ?
C4A H4A2 0.9800 . ?
O1A H1A2 0.8300 . ?
C11 C12 1.408(5) . ?
C11 C16 1.412(5) . ?
C12 C13 1.387(5) . ?
C12 C17 1.508(5) . ?
C13 C14 1.376(5) . ?
C13 H13 0.9400 . ?
C14 C15 1.384(6) . ?
C14 C18 1.505(5) . ?
C15 C16 1.394(5) . ?
C15 H15 0.9400 . ?
C16 C19 1.509(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C21 C26 1.405(5) . ?
C21 C22 1.414(5) . ?
C22 C23 1.395(5) . ?
C22 C27 1.517(5) . ?
C23 C24 1.378(6) . ?
C23 H23 0.9400 . ?
C24 C25 1.376(6) . ?
C24 C28 1.515(6) . ?
C25 C26 1.391(5) . ?
C25 H25 0.9400 . ?
C26 C29 1.513(5) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 H27C 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 H28C 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 H29C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 C11 101.7(6) . . ?
C1 P1 C21 114.0(6) . . ?
C11 P1 C21 106.32(16) . . ?
C1 P1 C1A 12.3(7) . . ?
C11 P1 C1A 94.6(5) . . ?
C21 P1 C1A 107.1(7) . . ?
C2 C1 P1 126.1(11) . . ?
C2 C1 H1 117.0 . . ?
P1 C1 H1 117.0 . . ?
C1 C2 C3 132.0(10) . . ?
C1 C2 H2 114.0 . . ?
C3 C2 H2 114.0 . . ?
C2 C3 C4 118.9(8) . . ?
C2 C3 H3A 107.6 . . ?
C4 C3 H3A 107.6 . . ?
C2 C3 H3B 107.6 . . ?
C4 C3 H3B 107.6 . . ?
H3A C3 H3B 107.0 . . ?
O1 C4 C3 108.2(7) . . ?
O1 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
O1 C4 H4B 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
C2A C1A P1 126.5(13) . . ?
C2A C1A H1A1 116.7 . . ?
P1 C1A H1A1 116.7 . . ?
C1A C2A C3A 131.3(14) . . ?
C1A C2A H2A 114.3 . . ?
C3A C2A H2A 114.3 . . ?
C4A C3A C2A 108.3(11) . . ?
C4A C3A H3A1 110.0 . . ?
C2A C3A H3A1 110.0 . . ?
C4A C3A H3A2 110.0 . . ?
C2A C3A H3A2 110.0 . . ?
H3A1 C3A H3A2 108.4 . . ?
O1A C4A C3A 98.0(11) . . ?
O1A C4A H4A1 112.2 . . ?
C3A C4A H4A1 112.2 . . ?
O1A C4A H4A2 112.2 . . ?
C3A C4A H4A2 112.2 . . ?
H4A1 C4A H4A2 109.8 . . ?
C4A O1A H1A2 109.5 . . ?
C12 C11 C16 118.5(3) . . ?
C12 C11 P1 125.3(3) . . ?
C16 C11 P1 116.2(3) . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 C17 117.8(3) . . ?
C11 C12 C17 122.9(3) . . ?
C14 C13 C12 123.0(4) . . ?
C14 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
C13 C14 C15 117.3(4) . . ?
C13 C14 C18 121.5(4) . . ?
C15 C14 C18 121.3(4) . . ?
C14 C15 C16 122.4(4) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
C15 C16 C11 119.4(4) . . ?
C15 C16 C19 118.5(4) . . ?
C11 C16 C19 122.1(3) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C26 C21 C22 118.6(3) . . ?
C26 C21 P1 126.4(3) . . ?
C22 C21 P1 114.6(3) . . ?
C23 C22 C21 119.2(4) . . ?
C23 C22 C27 118.2(3) . . ?
C21 C22 C27 122.6(3) . . ?
C24 C23 C22 122.8(4) . . ?
C24 C23 H23 118.6 . . ?
C22 C23 H23 118.6 . . ?
C25 C24 C23 116.9(4) . . ?
C25 C24 C28 122.2(4) . . ?
C23 C24 C28 120.9(4) . . ?
C24 C25 C26 123.5(4) . . ?
C24 C25 H25 118.2 . . ?
C26 C25 H25 118.2 . . ?
C25 C26 C21 119.0(4) . . ?
C25 C26 C29 116.4(4) . . ?
C21 C26 C29 124.6(4) . . ?
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 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 P1 C1 C2 -125.9(16) . . . . ?
C21 P1 C1 C2 120.1(16) . . . . ?
C1A P1 C1 C2 178(7) . . . . ?
P1 C1 C2 C3 173.3(10) . . . . ?
C1 C2 C3 C4 -19(2) . . . . ?
C2 C3 C4 O1 -90.0(11) . . . . ?
C1 P1 C1A C2A 4(4) . . . . ?
C11 P1 C1A C2A -121.9(19) . . . . ?
C21 P1 C1A C2A 129.5(19) . . . . ?
P1 C1A C2A C3A -173.0(15) . . . . ?
C1A C2A C3A C4A -132(2) . . . . ?
C2A C3A C4A O1A 156.6(13) . . . . ?
C1 P1 C11 C12 -85.4(6) . . . . ?
C21 P1 C11 C12 34.1(3) . . . . ?
C1A P1 C11 C12 -75.2(7) . . . . ?
C1 P1 C11 C16 94.5(6) . . . . ?
C21 P1 C11 C16 -145.9(3) . . . . ?
C1A P1 C11 C16 104.8(7) . . . . ?
C16 C11 C12 C13 1.7(5) . . . . ?
P1 C11 C12 C13 -178.3(3) . . . . ?
C16 C11 C12 C17 -178.4(3) . . . . ?
P1 C11 C12 C17 1.5(5) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C17 C12 C13 C14 -179.6(4) . . . . ?
C12 C13 C14 C15 -1.8(6) . . . . ?
C12 C13 C14 C18 177.7(4) . . . . ?
C13 C14 C15 C16 1.4(6) . . . . ?
C18 C14 C15 C16 -178.1(4) . . . . ?
C14 C15 C16 C11 0.5(6) . . . . ?
C14 C15 C16 C19 -179.8(4) . . . . ?
C12 C11 C16 C15 -2.1(5) . . . . ?
P1 C11 C16 C15 178.0(3) . . . . ?
C12 C11 C16 C19 178.3(4) . . . . ?
P1 C11 C16 C19 -1.7(5) . . . . ?
C1 P1 C21 C26 -9.1(7) . . . . ?
C11 P1 C21 C26 -120.3(3) . . . . ?
C1A P1 C21 C26 -20.0(6) . . . . ?
C1 P1 C21 C22 177.4(6) . . . . ?
C11 P1 C21 C22 66.3(3) . . . . ?
C1A P1 C21 C22 166.5(5) . . . . ?
C26 C21 C22 C23 1.9(5) . . . . ?
P1 C21 C22 C23 175.9(3) . . . . ?
C26 C21 C22 C27 -179.4(3) . . . . ?
P1 C21 C22 C27 -5.4(4) . . . . ?
C21 C22 C23 C24 -1.5(5) . . . . ?
C27 C22 C23 C24 179.7(3) . . . . ?
C22 C23 C24 C25 0.0(6) . . . . ?
C22 C23 C24 C28 179.8(4) . . . . ?
C23 C24 C25 C26 1.1(6) . . . . ?
C28 C24 C25 C26 -178.7(4) . . . . ?
C24 C25 C26 C21 -0.7(6) . . . . ?
C24 C25 C26 C29 177.0(4) . . . . ?
C22 C21 C26 C25 -0.8(5) . . . . ?
P1 C21 C26 C25 -174.0(3) . . . . ?
C22 C21 C26 C29 -178.3(3) . . . . ?
P1 C21 C26 C29 8.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.042
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_erk7924
_database_code_depnum_ccdc_archive 'CCDC 1419593'
_audit_update_record             
;
2015-08-19 deposited with the CCDC.
2015-12-23 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H29 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         324.42

_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                   8.3322(2)
_cell_length_b                   8.5865(3)
_cell_length_c                   13.0867(4)
_cell_angle_alpha                87.8330(10)
_cell_angle_beta                 85.9450(10)
_cell_angle_gamma                86.3220(10)
_cell_volume                     931.49(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9925
_cell_measurement_theta_min      5.1647
_cell_measurement_theta_max      67.8181
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352

_exptl_absorpt_coefficient_mu    1.262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.88

_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  'KappaCCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            23717
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_theta_min         3.39
_diffrn_reflns_theta_max         68.15
_diffrn_reflns_theta_full        68.15
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
The cyclopropane ring is disordered over two positions. 
Several restraints (SADI, SAME, ISOR and SIMU) were used in order
to improve refinement stability.
;

_reflns_number_total             3344
_reflns_number_gt                2937
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0925
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.059
_refine_ls_number_reflns         3344
_refine_ls_number_parameters     242
_refine_ls_number_restraints     52
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0413P)²+0.4035P] 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         0.304
_refine_diff_density_min         -0.272
_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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 v.2014.5-0 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'SHELXL2014 (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 0.69479(4) 0.40671(4) 0.20257(3) 0.02122(12) Uani d . . . 1.0 . .
C C1 0.6944(2) 0.61588(19) 0.23567(15) 0.0339(4) Uani d . . D 1.0 . .
H H1A 0.7195 0.6803 0.1729 0.041 Uiso calc U P R 0.615(5) A 1
H H1B 0.5862 0.6517 0.2651 0.041 Uiso calc U P R 0.615(5) A 1
H H1C 0.6519 0.6849 0.1802 0.041 Uiso calc U P R 0.385(5) A 2
H H1D 0.6283 0.6361 0.3002 0.041 Uiso calc U P R 0.385(5) A 2
C C2 0.8206(3) 0.6360(3) 0.3138(2) 0.0242(8) Uani d U P D 0.615(5) A 1
H H2 0.8076 0.5759 0.3805 0.029 Uiso calc U P R 0.615(5) A 1
C C3 0.9894(4) 0.6549(3) 0.2698(2) 0.0322(9) Uani d U P D 0.615(5) A 1
H H3A 1.0092 0.6552 0.1943 0.039 Uiso calc U P R 0.615(5) A 1
H H3B 1.0788 0.6067 0.3085 0.039 Uiso calc U P R 0.615(5) A 1
C C4 0.8907(13) 0.7917(8) 0.3161(10) 0.036(2) Uani d U P D 0.615(5) A 1
H H4A 0.9198 0.8273 0.3831 0.044 Uiso calc U P R 0.615(5) A 1
H H4B 0.8503 0.8757 0.2689 0.044 Uiso calc U P R 0.615(5) A 1
C C2A 0.8783(6) 0.6422(5) 0.2484(4) 0.0266(13) Uani d U P D 0.385(5) A 2
H H2A 0.9597 0.6046 0.1935 0.032 Uiso calc U P R 0.385(5) A 2
C C3A 0.9234(6) 0.6276(5) 0.3577(4) 0.0342(14) Uani d U P D 0.385(5) A 2
H H3A1 1.0326 0.5824 0.3709 0.041 Uiso calc U P R 0.385(5) A 2
H H3A2 0.838 0.6028 0.4112 0.041 Uiso calc U P R 0.385(5) A 2
C C4A 0.910(2) 0.7866(12) 0.3030(14) 0.031(3) Uani d U P D 0.385(5) A 2
H H4A1 0.8164 0.8585 0.3233 0.037 Uiso calc U P R 0.385(5) A 2
H H4A2 1.0109 0.8381 0.2829 0.037 Uiso calc U P R 0.385(5) A 2
C C11 0.67236(18) 0.31641(17) 0.33356(12) 0.0221(3) Uani d . . . 1.0 . .
C C12 0.52873(18) 0.32357(18) 0.39797(12) 0.0240(3) Uani d . . . 1.0 . .
C C13 0.5260(2) 0.24512(19) 0.49324(12) 0.0273(4) Uani d . . . 1.0 . .
H H13 0.4283 0.2484 0.5354 0.033 Uiso calc U . R 1.0 . .
C C14 0.6604(2) 0.16252(18) 0.52892(12) 0.0274(4) Uani d . . . 1.0 . .
C C15 0.80164(19) 0.16061(18) 0.46624(13) 0.0270(4) Uani d . . . 1.0 . .
H H15 0.8959 0.1072 0.4901 0.032 Uiso calc U . R 1.0 . .
C C16 0.81048(18) 0.23409(17) 0.36950(12) 0.0247(3) Uani d . . . 1.0 . .
C C17 0.37429(19) 0.4109(2) 0.36951(12) 0.0291(4) Uani d . . . 1.0 . .
H H17A 0.32 0.349 0.3225 0.044 Uiso calc U . R 1.0 . .
H H17B 0.399 0.5113 0.336 0.044 Uiso calc U . R 1.0 . .
H H17C 0.3036 0.429 0.4316 0.044 Uiso calc U . R 1.0 . .
C C18 0.6536(2) 0.0782(2) 0.63205(13) 0.0357(4) Uani d . . . 1.0 . .
H H18A 0.6511 -0.0343 0.6227 0.054 Uiso calc U . R 1.0 . .
H H18B 0.5562 0.1152 0.6727 0.054 Uiso calc U . R 1.0 . .
H H18C 0.749 0.0989 0.6679 0.054 Uiso calc U . R 1.0 . .
C C19 0.96947(19) 0.2203(2) 0.30634(15) 0.0329(4) Uani d . . . 1.0 . .
H H19A 1.0525 0.1708 0.3483 0.049 Uiso calc U . R 1.0 . .
H H19B 1.0004 0.3246 0.2828 0.049 Uiso calc U . R 1.0 . .
H H19C 0.9585 0.1567 0.2469 0.049 Uiso calc U . R 1.0 . .
C C21 0.50503(17) 0.36262(17) 0.14738(11) 0.0193(3) Uani d . . . 1.0 . .
C C22 0.49249(18) 0.20076(17) 0.13364(11) 0.0208(3) Uani d . . . 1.0 . .
C C23 0.35545(19) 0.14840(17) 0.09455(11) 0.0230(3) Uani d . . . 1.0 . .
H H23 0.3471 0.0393 0.0886 0.028 Uiso calc U . R 1.0 . .
C C24 0.23051(18) 0.25030(18) 0.06393(11) 0.0230(3) Uani d . . . 1.0 . .
C C25 0.24846(18) 0.40894(18) 0.07171(11) 0.0217(3) Uani d . . . 1.0 . .
H H25 0.1665 0.4807 0.0482 0.026 Uiso calc U . R 1.0 . .
C C26 0.38139(17) 0.46757(17) 0.11246(11) 0.0196(3) Uani d . . . 1.0 . .
C C27 0.62515(19) 0.07987(17) 0.15835(13) 0.0264(4) Uani d . . . 1.0 . .
H H27A 0.6331 0.0712 0.2327 0.04 Uiso calc U . R 1.0 . .
H H27B 0.7278 0.1113 0.1252 0.04 Uiso calc U . R 1.0 . .
H H27C 0.6006 -0.0214 0.1331 0.04 Uiso calc U . R 1.0 . .
C C28 0.08232(19) 0.1905(2) 0.02278(13) 0.0302(4) Uani d . . . 1.0 . .
H H28A -0.0111 0.2622 0.0401 0.045 Uiso calc U . R 1.0 . .
H H28B 0.0635 0.0867 0.0533 0.045 Uiso calc U . R 1.0 . .
H H28C 0.0983 0.1837 -0.0519 0.045 Uiso calc U . R 1.0 . .
C C29 0.38250(18) 0.64312(17) 0.11644(12) 0.0232(3) Uani d . . . 1.0 . .
H H29A 0.2909 0.6915 0.0814 0.035 Uiso calc U . R 1.0 . .
H H29B 0.4832 0.6779 0.0824 0.035 Uiso calc U . R 1.0 . .
H H29C 0.3741 0.6738 0.1881 0.035 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 C21 . 1.8504(15) ?
P1 C11 . 1.8567(16) ?
P1 C1 . 1.8631(17) ?
C1 C2 . 1.539(3) ?
C1 C2A . 1.585(5) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C1 H1C . 0.99 ?
C1 H1D . 0.99 ?
C2 C4 . 1.495(8) ?
C2 C3 . 1.498(4) ?
C2 H2 . 1.0 ?
C3 C4 . 1.511(9) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C2A C4A . 1.501(11) ?
C2A C3A . 1.503(7) ?
C2A H2A . 1.0 ?
C3A C4A . 1.519(13) ?
C3A H3A1 . 0.99 ?
C3A H3A2 . 0.99 ?
C4A H4A1 . 0.99 ?
C4A H4A2 . 0.99 ?
C11 C16 . 1.411(2) ?
C11 C12 . 1.414(2) ?
C12 C13 . 1.394(2) ?
C12 C17 . 1.510(2) ?
C13 C14 . 1.386(2) ?
C13 H13 . 0.95 ?
C14 C15 . 1.386(2) ?
C14 C18 . 1.506(2) ?
C15 C16 . 1.392(2) ?
C15 H15 . 0.95 ?
C16 C19 . 1.511(2) ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C21 C26 . 1.414(2) ?
C21 C22 . 1.420(2) ?
C22 C23 . 1.390(2) ?
C22 C27 . 1.511(2) ?
C23 C24 . 1.388(2) ?
C23 H23 . 0.95 ?
C24 C25 . 1.388(2) ?
C24 C28 . 1.508(2) ?
C25 C26 . 1.393(2) ?
C25 H25 . 0.95 ?
C26 C29 . 1.511(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 ?

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
C21 P1 C11 . . 102.63(7) ?
C21 P1 C1 . . 111.67(7) ?
C11 P1 C1 . . 99.54(8) ?
C2 C1 P1 . . 109.89(13) ?
C2A C1 P1 . . 103.94(18) ?
C2 C1 H1A . . 109.7 ?
P1 C1 H1A . . 109.7 ?
C2 C1 H1B . . 109.7 ?
P1 C1 H1B . . 109.7 ?
H1A C1 H1B . . 108.2 ?
C2A C1 H1C . . 111.0 ?
P1 C1 H1C . . 111.0 ?
C2A C1 H1D . . 111.0 ?
P1 C1 H1D . . 111.0 ?
H1C C1 H1D . . 109.0 ?
C4 C2 C3 . . 60.6(5) ?
C4 C2 C1 . . 117.7(5) ?
C3 C2 C1 . . 115.9(3) ?
C4 C2 H2 . . 116.9 ?
C3 C2 H2 . . 116.9 ?
C1 C2 H2 . . 116.9 ?
C2 C3 C4 . . 59.6(4) ?
C2 C3 H3A . . 117.8 ?
C4 C3 H3A . . 117.8 ?
C2 C3 H3B . . 117.8 ?
C4 C3 H3B . . 117.8 ?
H3A C3 H3B . . 115.0 ?
C2 C4 C3 . . 59.8(3) ?
C2 C4 H4A . . 117.8 ?
C3 C4 H4A . . 117.8 ?
C2 C4 H4B . . 117.8 ?
C3 C4 H4B . . 117.8 ?
H4A C4 H4B . . 114.9 ?
C4A C2A C3A . . 60.7(7) ?
C4A C2A C1 . . 115.5(8) ?
C3A C2A C1 . . 113.5(4) ?
C4A C2A H2A . . 118.1 ?
C3A C2A H2A . . 118.1 ?
C1 C2A H2A . . 118.1 ?
C2A C3A C4A . . 59.6(6) ?
C2A C3A H3A1 . . 117.8 ?
C4A C3A H3A1 . . 117.8 ?
C2A C3A H3A2 . . 117.8 ?
C4A C3A H3A2 . . 117.8 ?
H3A1 C3A H3A2 . . 115.0 ?
C2A C4A C3A . . 59.7(4) ?
C2A C4A H4A1 . . 117.8 ?
C3A C4A H4A1 . . 117.8 ?
C2A C4A H4A2 . . 117.8 ?
C3A C4A H4A2 . . 117.8 ?
H4A1 C4A H4A2 . . 114.9 ?
C16 C11 C12 . . 118.70(14) ?
C16 C11 P1 . . 116.37(12) ?
C12 C11 P1 . . 124.93(11) ?
C13 C12 C11 . . 119.24(14) ?
C13 C12 C17 . . 116.95(14) ?
C11 C12 C17 . . 123.80(14) ?
C14 C13 C12 . . 122.56(15) ?
C14 C13 H13 . . 118.7 ?
C12 C13 H13 . . 118.7 ?
C15 C14 C13 . . 117.51(15) ?
C15 C14 C18 . . 121.14(15) ?
C13 C14 C18 . . 121.35(15) ?
C14 C15 C16 . . 122.41(15) ?
C14 C15 H15 . . 118.8 ?
C16 C15 H15 . . 118.8 ?
C15 C16 C11 . . 119.54(15) ?
C15 C16 C19 . . 117.92(14) ?
C11 C16 C19 . . 122.54(15) ?
C12 C17 H17A . . 109.5 ?
C12 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C12 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C14 C18 H18A . . 109.5 ?
C14 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C14 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C16 C19 H19A . . 109.5 ?
C16 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C16 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C26 C21 C22 . . 118.01(13) ?
C26 C21 P1 . . 128.74(11) ?
C22 C21 P1 . . 113.11(11) ?
C23 C22 C21 . . 120.08(14) ?
C23 C22 C27 . . 117.45(13) ?
C21 C22 C27 . . 122.46(13) ?
C24 C23 C22 . . 122.13(14) ?
C24 C23 H23 . . 118.9 ?
C22 C23 H23 . . 118.9 ?
C23 C24 C25 . . 117.31(14) ?
C23 C24 C28 . . 121.11(14) ?
C25 C24 C28 . . 121.57(14) ?
C24 C25 C26 . . 122.90(14) ?
C24 C25 H25 . . 118.5 ?
C26 C25 H25 . . 118.5 ?
C25 C26 C21 . . 119.36(13) ?
C25 C26 C29 . . 116.53(13) ?
C21 C26 C29 . . 124.11(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 ?

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
C21 P1 C1 C2 . . . . 160.01(15) ?
C11 P1 C1 C2 . . . . 52.22(17) ?
C21 P1 C1 C2A . . . . -163.3(2) ?
C11 P1 C1 C2A . . . . 88.9(2) ?
P1 C1 C2 C4 . . . . 153.8(5) ?
P1 C1 C2 C3 . . . . 84.9(2) ?
C1 C2 C3 C4 . . . . 108.7(6) ?
C1 C2 C4 C3 . . . . -105.7(4) ?
P1 C1 C2A C4A . . . . -163.8(8) ?
P1 C1 C2A C3A . . . . -96.3(3) ?
C1 C2A C3A C4A . . . . -107.1(9) ?
C1 C2A C4A C3A . . . . 103.8(6) ?
C21 P1 C11 C16 . . . . 137.86(11) ?
C1 P1 C11 C16 . . . . -107.21(12) ?
C21 P1 C11 C12 . . . . -41.66(14) ?
C1 P1 C11 C12 . . . . 73.27(14) ?
C16 C11 C12 C13 . . . . -2.2(2) ?
P1 C11 C12 C13 . . . . 177.35(11) ?
C16 C11 C12 C17 . . . . 178.53(14) ?
P1 C11 C12 C17 . . . . -2.0(2) ?
C11 C12 C13 C14 . . . . 1.5(2) ?
C17 C12 C13 C14 . . . . -179.11(14) ?
C12 C13 C14 C15 . . . . 0.4(2) ?
C12 C13 C14 C18 . . . . -179.71(15) ?
C13 C14 C15 C16 . . . . -1.8(2) ?
C18 C14 C15 C16 . . . . 178.34(15) ?
C14 C15 C16 C11 . . . . 1.2(2) ?
C14 C15 C16 C19 . . . . -178.14(15) ?
C12 C11 C16 C15 . . . . 0.9(2) ?
P1 C11 C16 C15 . . . . -178.68(11) ?
C12 C11 C16 C19 . . . . -179.86(14) ?
P1 C11 C16 C19 . . . . 0.6(2) ?
C11 P1 C21 C26 . . . . 117.96(13) ?
C1 P1 C21 C26 . . . . 12.19(16) ?
C11 P1 C21 C22 . . . . -66.53(11) ?
C1 P1 C21 C22 . . . . -172.31(11) ?
C26 C21 C22 C23 . . . . -5.1(2) ?
P1 C21 C22 C23 . . . . 178.85(11) ?
C26 C21 C22 C27 . . . . 173.81(13) ?
P1 C21 C22 C27 . . . . -2.22(18) ?
C21 C22 C23 C24 . . . . 2.7(2) ?
C27 C22 C23 C24 . . . . -176.31(14) ?
C22 C23 C24 C25 . . . . 1.3(2) ?
C22 C23 C24 C28 . . . . -179.37(14) ?
C23 C24 C25 C26 . . . . -2.8(2) ?
C28 C24 C25 C26 . . . . 177.85(14) ?
C24 C25 C26 C21 . . . . 0.3(2) ?
C24 C25 C26 C29 . . . . -179.51(13) ?
C22 C21 C26 C25 . . . . 3.7(2) ?
P1 C21 C26 C25 . . . . 178.97(11) ?
C22 C21 C26 C29 . . . . -176.52(13) ?
P1 C21 C26 C29 . . . . -1.2(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_erk7949
_database_code_depnum_ccdc_archive 'CCDC 1419594'
_audit_update_record             
;
2015-08-19 deposited with the CCDC.
2015-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H37 B F15 O P Si'
_chemical_formula_weight         924.60

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   10.8091(2)
_cell_length_b                   25.3584(3)
_cell_length_c                   16.9567(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.133(1)
_cell_angle_gamma                90.00
_cell_volume                     4621.25(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    10495
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9603
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32591
_diffrn_reflns_av_R_equivalents  0.064
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.12
_diffrn_reflns_theta_max         25.00
_reflns_number_total             8012
_reflns_number_gt                5621
_reflns_threshold_expression     >2sigma(I)

_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.

 A disordered dichloromethan molecule was found in the asymmetrical unit
 and could not be satisfactorily refined. The program SQUEEZE (A. L. Spek
 J. Appl. Cryst., 2003, 36, 7-13) was therefore used to remove 
 mathematically the effect of the solvent.
 The quoted formula and derived parameters are not included the squeezed
 solvent molecule.  
;

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.000 302 36 ' '
2 0.500 0.500 0.500 302 36 ' '




_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0882P)²+4.8400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8012
_refine_ls_number_parameters     568
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.1966
_refine_ls_wR_factor_gt          0.1800
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.37417(8) 0.31516(3) 0.20392(5) 0.0338(2) Uani 1 1 d . . .
C1 C 0.2176(3) 0.32983(13) 0.2249(2) 0.0349(8) Uani 1 1 d . . .
H1 H 0.2070 0.3354 0.2815 0.042 Uiso 1 1 calc R . .
C2 C 0.2377(3) 0.27269(12) 0.2008(2) 0.0329(7) Uani 1 1 d . . .
H2 H 0.2001 0.2631 0.1469 0.039 Uiso 1 1 calc R . .
C3 C 0.2381(3) 0.22888(13) 0.2626(2) 0.0345(8) Uani 1 1 d . . .
H3A H 0.2636 0.2438 0.3151 0.041 Uiso 1 1 calc R . .
H3B H 0.3001 0.2024 0.2518 0.041 Uiso 1 1 calc R . .
C4 C 0.1428(4) 0.36604(13) 0.1676(2) 0.0421(9) Uani 1 1 d . . .
H4A H 0.1584 0.3573 0.1132 0.050 Uiso 1 1 calc R . .
H4B H 0.0539 0.3611 0.1720 0.050 Uiso 1 1 calc R . .
O1 O 0.1756(3) 0.41905(10) 0.18396(17) 0.0527(7) Uani 1 1 d . . .
Si1 Si 0.08720(13) 0.46476(4) 0.22001(7) 0.0527(3) Uani 1 1 d . . .
C5 C -0.0750(5) 0.45956(18) 0.1731(3) 0.0658(13) Uani 1 1 d . . .
H5A H -0.0770 0.4657 0.1165 0.099 Uiso 1 1 calc R . .
H5B H -0.1262 0.4856 0.1961 0.099 Uiso 1 1 calc R . .
H5C H -0.1069 0.4246 0.1821 0.099 Uiso 1 1 calc R . .
C6 C 0.1605(6) 0.52729(17) 0.1945(3) 0.0758(16) Uani 1 1 d . . .
H6A H 0.1652 0.5287 0.1378 0.114 Uiso 1 1 calc R . .
H6B H 0.2437 0.5294 0.2222 0.114 Uiso 1 1 calc R . .
H6C H 0.1111 0.5567 0.2102 0.114 Uiso 1 1 calc R . .
C7 C 0.0890(6) 0.4574(2) 0.3284(3) 0.0775(15) Uani 1 1 d . . .
H7A H 0.0607 0.4223 0.3405 0.116 Uiso 1 1 calc R . .
H7B H 0.0343 0.4834 0.3482 0.116 Uiso 1 1 calc R . .
H7C H 0.1731 0.4626 0.3535 0.116 Uiso 1 1 calc R . .
C11 C 0.4290(3) 0.34192(14) 0.1156(2) 0.0400(8) Uani 1 1 d . . .
C12 C 0.4918(4) 0.39122(15) 0.1233(2) 0.0486(10) Uani 1 1 d . . .
C13 C 0.5437(4) 0.41016(19) 0.0569(3) 0.0637(13) Uani 1 1 d . . .
H13 H 0.5873 0.4423 0.0613 0.076 Uiso 1 1 calc R . .
C14 C 0.5343(4) 0.3841(2) -0.0151(3) 0.0626(12) Uani 1 1 d . . .
C15 C 0.4687(4) 0.33756(19) -0.0210(2) 0.0577(11) Uani 1 1 d . . .
H15 H 0.4589 0.3201 -0.0702 0.069 Uiso 1 1 calc R . .
C16 C 0.4157(4) 0.31498(16) 0.0429(2) 0.0439(9) Uani 1 1 d . . .
C17 C 0.5027(5) 0.42342(17) 0.1976(3) 0.0654(13) Uani 1 1 d . . .
H17A H 0.5485 0.4555 0.1893 0.098 Uiso 1 1 calc R . .
H17B H 0.5466 0.4033 0.2405 0.098 Uiso 1 1 calc R . .
H17C H 0.4203 0.4323 0.2110 0.098 Uiso 1 1 calc R . .
C18 C 0.5949(6) 0.4056(3) -0.0847(4) 0.096(2) Uani 1 1 d . . .
H18A H 0.6676 0.3847 -0.0925 0.144 Uiso 1 1 calc R . .
H18B H 0.6197 0.4419 -0.0741 0.144 Uiso 1 1 calc R . .
H18C H 0.5362 0.4042 -0.1321 0.144 Uiso 1 1 calc R . .
C19 C 0.3461(4) 0.26383(17) 0.0282(2) 0.0548(11) Uani 1 1 d . . .
H19A H 0.2573 0.2705 0.0242 0.082 Uiso 1 1 calc R . .
H19B H 0.3690 0.2398 0.0718 0.082 Uiso 1 1 calc R . .
H19C H 0.3672 0.2483 -0.0209 0.082 Uiso 1 1 calc R . .
C21 C 0.4843(3) 0.30207(15) 0.2886(2) 0.0404(9) Uani 1 1 d . . .
C22 C 0.5669(3) 0.25956(15) 0.2815(2) 0.0420(9) Uani 1 1 d . . .
C23 C 0.6491(4) 0.24604(18) 0.3476(2) 0.0514(10) Uani 1 1 d . . .
H23 H 0.7057 0.2183 0.3433 0.062 Uiso 1 1 calc R . .
C24 C 0.6499(4) 0.2719(2) 0.4186(2) 0.0589(12) Uani 1 1 d . . .
C25 C 0.5701(4) 0.3139(2) 0.4237(2) 0.0598(12) Uani 1 1 d . . .
H25 H 0.5733 0.3325 0.4718 0.072 Uiso 1 1 calc R . .
C26 C 0.4849(4) 0.33022(17) 0.3608(2) 0.0486(10) Uani 1 1 d . . .
C27 C 0.5691(4) 0.22884(16) 0.2057(2) 0.0498(10) Uani 1 1 d . . .
H27A H 0.6353 0.2029 0.2121 0.075 Uiso 1 1 calc R . .
H27B H 0.5834 0.2527 0.1629 0.075 Uiso 1 1 calc R . .
H27C H 0.4899 0.2111 0.1931 0.075 Uiso 1 1 calc R . .
C28 C 0.7362(5) 0.2545(3) 0.4901(3) 0.0866(18) Uani 1 1 d . . .
H28A H 0.7068 0.2214 0.5099 0.130 Uiso 1 1 calc R . .
H28B H 0.7375 0.2811 0.5313 0.130 Uiso 1 1 calc R . .
H28C H 0.8195 0.2498 0.4750 0.130 Uiso 1 1 calc R . .
C29 C 0.3993(5) 0.3754(2) 0.3754(3) 0.0743(15) Uani 1 1 d . . .
H29A H 0.3299 0.3624 0.4016 0.111 Uiso 1 1 calc R . .
H29B H 0.3683 0.3913 0.3251 0.111 Uiso 1 1 calc R . .
H29C H 0.4447 0.4016 0.4087 0.111 Uiso 1 1 calc R . .
B1 B 0.1023(4) 0.19968(15) 0.2641(2) 0.0339(9) Uani 1 1 d . . .
C31 C 0.1102(3) 0.15618(13) 0.3384(2) 0.0364(8) Uani 1 1 d . . .
F32 F -0.0781(2) 0.17962(10) 0.39043(14) 0.0561(6) Uani 1 1 d . . .
C32 C 0.0247(4) 0.14904(15) 0.3919(2) 0.0441(9) Uani 1 1 d . . .
F33 F -0.0556(3) 0.10618(11) 0.49998(15) 0.0784(8) Uani 1 1 d . . .
C33 C 0.0316(4) 0.11013(17) 0.4500(2) 0.0526(11) Uani 1 1 d . . .
F34 F 0.1378(3) 0.03673(10) 0.51044(15) 0.0829(9) Uani 1 1 d . . .
C34 C 0.1285(5) 0.07549(16) 0.4561(2) 0.0547(12) Uani 1 1 d . . .
F35 F 0.3111(3) 0.04476(9) 0.40631(16) 0.0696(8) Uani 1 1 d . . .
C35 C 0.2163(4) 0.07967(14) 0.4038(2) 0.0501(10) Uani 1 1 d . . .
F36 F 0.2935(2) 0.11858(9) 0.29576(15) 0.0580(6) Uani 1 1 d . . .
C36 C 0.2052(4) 0.11888(14) 0.3468(2) 0.0439(9) Uani 1 1 d . . .
C41 C 0.0586(4) 0.16231(13) 0.1857(2) 0.0375(8) Uani 1 1 d . . .
F42 F -0.1420(2) 0.15347(8) 0.22736(13) 0.0507(6) Uani 1 1 d . . .
C42 C -0.0589(4) 0.14068(14) 0.1757(2) 0.0415(9) Uani 1 1 d . . .
F43 F -0.2183(3) 0.08675(11) 0.11124(16) 0.0766(8) Uani 1 1 d . . .
C43 C -0.1013(4) 0.10528(15) 0.1167(2) 0.0512(10) Uani 1 1 d . . .
F44 F -0.0620(3) 0.05578(10) 0.00473(15) 0.0826(9) Uani 1 1 d . . .
C44 C -0.0227(5) 0.09007(15) 0.0631(2) 0.0569(12) Uani 1 1 d . . .
F45 F 0.1726(3) 0.09712(11) 0.01493(15) 0.0788(9) Uani 1 1 d . . .
C45 C 0.0941(5) 0.11055(16) 0.0682(2) 0.0553(11) Uani 1 1 d . . .
F46 F 0.2504(2) 0.16347(9) 0.12818(15) 0.0603(6) Uani 1 1 d . . .
C46 C 0.1308(4) 0.14579(14) 0.1283(2) 0.0445(9) Uani 1 1 d . . .
C51 C 0.0031(3) 0.24829(13) 0.27493(19) 0.0332(8) Uani 1 1 d . . .
F52 F -0.0871(2) 0.24950(8) 0.14062(12) 0.0515(6) Uani 1 1 d . . .
C52 C -0.0801(3) 0.26939(13) 0.2153(2) 0.0369(8) Uani 1 1 d . . .
F53 F -0.2360(2) 0.32923(9) 0.16282(15) 0.0610(7) Uani 1 1 d . . .
C53 C -0.1572(3) 0.31211(14) 0.2245(2) 0.0441(9) Uani 1 1 d . . .
F54 F -0.2268(2) 0.37777(9) 0.30663(18) 0.0716(8) Uani 1 1 d . . .
C54 C -0.1517(4) 0.33657(14) 0.2964(3) 0.0484(10) Uani 1 1 d . . .
F55 F -0.0632(3) 0.34280(10) 0.42781(16) 0.0743(8) Uani 1 1 d . . .
C55 C -0.0697(4) 0.31909(15) 0.3568(2) 0.0486(10) Uani 1 1 d . . .
F56 F 0.0863(2) 0.26210(9) 0.40828(13) 0.0569(6) Uani 1 1 d . . .
C56 C 0.0060(3) 0.27656(15) 0.3450(2) 0.0425(9) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C21 1.795(3) . ?
P1 C11 1.802(4) . ?
P1 C1 1.804(4) . ?
P1 C2 1.822(3) . ?
C1 C4 1.508(5) . ?
C1 C2 1.527(5) . ?
C1 H1 0.9900 . ?
C2 C3 1.527(5) . ?
C2 H2 0.9900 . ?
C3 B1 1.647(5) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 O1 1.410(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
O1 Si1 1.660(3) . ?
Si1 C6 1.844(5) . ?
Si1 C7 1.846(5) . ?
Si1 C5 1.851(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C11 C16 1.403(5) . ?
C11 C12 1.422(5) . ?
C12 C13 1.397(6) . ?
C12 C17 1.494(6) . ?
C13 C14 1.382(7) . ?
C13 H13 0.9400 . ?
C14 C15 1.375(7) . ?
C14 C18 1.512(6) . ?
C15 C16 1.401(5) . ?
C15 H15 0.9400 . ?
C16 C19 1.507(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C21 C22 1.413(5) . ?
C21 C26 1.418(5) . ?
C22 C23 1.397(5) . ?
C22 C27 1.506(5) . ?
C23 C24 1.371(6) . ?
C23 H23 0.9400 . ?
C24 C25 1.379(7) . ?
C24 C28 1.515(6) . ?
C25 C26 1.394(6) . ?
C25 H25 0.9400 . ?
C26 C29 1.509(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 H27C 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 H28C 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 H29C 0.9700 . ?
B1 C51 1.657(5) . ?
B1 C41 1.660(5) . ?
B1 C31 1.670(5) . ?
C31 C32 1.374(5) . ?
C31 C36 1.392(5) . ?
F32 C32 1.354(5) . ?
C32 C33 1.391(5) . ?
F33 C33 1.337(5) . ?
C33 C34 1.362(6) . ?
F34 C34 1.344(4) . ?
C34 C35 1.370(6) . ?
F35 C35 1.352(5) . ?
C35 C36 1.383(5) . ?
F36 C36 1.355(4) . ?
C41 C46 1.376(5) . ?
C41 C42 1.377(5) . ?
F42 C42 1.359(4) . ?
C42 C43 1.386(5) . ?
F43 C43 1.343(5) . ?
C43 C44 1.364(6) . ?
F44 C44 1.351(5) . ?
C44 C45 1.360(7) . ?
F45 C45 1.347(5) . ?
C45 C46 1.382(6) . ?
F46 C46 1.369(5) . ?
C51 C56 1.385(5) . ?
C51 C52 1.387(5) . ?
F52 C52 1.357(4) . ?
C52 C53 1.386(5) . ?
F53 C53 1.347(4) . ?
C53 C54 1.364(6) . ?
F54 C54 1.345(4) . ?
C54 C55 1.356(6) . ?
F55 C55 1.340(4) . ?
C55 C56 1.381(5) . ?
F56 C56 1.356(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 P1 C11 119.05(17) . . ?
C21 P1 C1 115.87(17) . . ?
C11 P1 C1 119.01(16) . . ?
C21 P1 C2 112.31(16) . . ?
C11 P1 C2 122.37(17) . . ?
C1 P1 C2 49.81(15) . . ?
C4 C1 C2 119.2(3) . . ?
C4 C1 P1 116.6(3) . . ?
C2 C1 P1 65.70(18) . . ?
C4 C1 H1 115.4 . . ?
C2 C1 H1 115.4 . . ?
P1 C1 H1 115.4 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 P1 117.8(2) . . ?
C1 C2 P1 64.49(18) . . ?
C3 C2 H2 115.1 . . ?
C1 C2 H2 115.1 . . ?
P1 C2 H2 115.1 . . ?
C2 C3 B1 113.6(3) . . ?
C2 C3 H3A 108.8 . . ?
B1 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
B1 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
O1 C4 C1 110.3(3) . . ?
O1 C4 H4A 109.6 . . ?
C1 C4 H4A 109.6 . . ?
O1 C4 H4B 109.6 . . ?
C1 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C4 O1 Si1 126.6(3) . . ?
O1 Si1 C6 103.6(2) . . ?
O1 Si1 C7 110.5(2) . . ?
C6 Si1 C7 111.2(2) . . ?
O1 Si1 C5 110.37(19) . . ?
C6 Si1 C5 111.8(2) . . ?
C7 Si1 C5 109.2(3) . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Si1 C6 H6A 109.5 . . ?
Si1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
Si1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C16 C11 C12 120.9(4) . . ?
C16 C11 P1 122.3(3) . . ?
C12 C11 P1 116.8(3) . . ?
C13 C12 C11 117.2(4) . . ?
C13 C12 C17 119.3(4) . . ?
C11 C12 C17 123.6(4) . . ?
C14 C13 C12 123.4(4) . . ?
C14 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
C15 C14 C13 117.6(4) . . ?
C15 C14 C18 121.1(5) . . ?
C13 C14 C18 121.3(5) . . ?
C14 C15 C16 123.0(4) . . ?
C14 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
C15 C16 C11 117.9(4) . . ?
C15 C16 C19 117.5(4) . . ?
C11 C16 C19 124.5(3) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C21 C26 120.9(3) . . ?
C22 C21 P1 116.4(3) . . ?
C26 C21 P1 122.7(3) . . ?
C23 C22 C21 118.2(4) . . ?
C23 C22 C27 119.4(4) . . ?
C21 C22 C27 122.4(3) . . ?
C24 C23 C22 122.1(4) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C23 C24 C25 118.6(4) . . ?
C23 C24 C28 120.6(5) . . ?
C25 C24 C28 120.8(5) . . ?
C24 C25 C26 123.2(4) . . ?
C24 C25 H25 118.4 . . ?
C26 C25 H25 118.4 . . ?
C25 C26 C21 116.9(4) . . ?
C25 C26 C29 117.8(4) . . ?
C21 C26 C29 125.2(4) . . ?
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 . . ?
C3 B1 C51 104.8(3) . . ?
C3 B1 C41 115.0(3) . . ?
C51 B1 C41 112.4(3) . . ?
C3 B1 C31 109.6(3) . . ?
C51 B1 C31 112.9(3) . . ?
C41 B1 C31 102.4(3) . . ?
C32 C31 C36 112.6(3) . . ?
C32 C31 B1 127.0(3) . . ?
C36 C31 B1 120.2(3) . . ?
F32 C32 C31 121.4(3) . . ?
F32 C32 C33 113.6(4) . . ?
C31 C32 C33 124.9(4) . . ?
F33 C33 C34 119.5(4) . . ?
F33 C33 C32 120.9(4) . . ?
C34 C33 C32 119.5(4) . . ?
F34 C34 C33 121.6(4) . . ?
F34 C34 C35 119.6(4) . . ?
C33 C34 C35 118.8(4) . . ?
F35 C35 C34 120.2(4) . . ?
F35 C35 C36 120.1(4) . . ?
C34 C35 C36 119.6(4) . . ?
F36 C36 C35 115.3(4) . . ?
F36 C36 C31 120.1(3) . . ?
C35 C36 C31 124.6(4) . . ?
C46 C41 C42 112.2(3) . . ?
C46 C41 B1 127.3(3) . . ?
C42 C41 B1 120.4(3) . . ?
F42 C42 C41 119.4(3) . . ?
F42 C42 C43 115.4(4) . . ?
C41 C42 C43 125.2(4) . . ?
F43 C43 C44 120.3(4) . . ?
F43 C43 C42 120.8(4) . . ?
C44 C43 C42 118.9(4) . . ?
F44 C44 C45 120.6(4) . . ?
F44 C44 C43 120.1(4) . . ?
C45 C44 C43 119.4(4) . . ?
F45 C45 C44 120.6(4) . . ?
F45 C45 C46 120.4(4) . . ?
C44 C45 C46 119.0(4) . . ?
F46 C46 C41 120.6(3) . . ?
F46 C46 C45 114.0(4) . . ?
C41 C46 C45 125.4(4) . . ?
C56 C51 C52 112.3(3) . . ?
C56 C51 B1 121.6(3) . . ?
C52 C51 B1 125.7(3) . . ?
F52 C52 C53 114.9(3) . . ?
F52 C52 C51 120.3(3) . . ?
C53 C52 C51 124.8(3) . . ?
F53 C53 C54 120.7(3) . . ?
F53 C53 C52 120.2(4) . . ?
C54 C53 C52 119.2(3) . . ?
F54 C54 C55 120.7(4) . . ?
F54 C54 C53 120.0(4) . . ?
C55 C54 C53 119.3(3) . . ?
F55 C55 C54 120.0(4) . . ?
F55 C55 C56 120.4(4) . . ?
C54 C55 C56 119.7(4) . . ?
F56 C56 C55 115.8(3) . . ?
F56 C56 C51 119.5(3) . . ?
C55 C56 C51 124.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 P1 C1 C4 150.0(3) . . . . ?
C11 P1 C1 C4 -2.4(3) . . . . ?
C2 P1 C1 C4 -111.8(3) . . . . ?
C21 P1 C1 C2 -98.2(2) . . . . ?
C11 P1 C1 C2 109.4(2) . . . . ?
C4 C1 C2 C3 -143.0(3) . . . . ?
P1 C1 C2 C3 108.8(3) . . . . ?
C4 C1 C2 P1 108.1(3) . . . . ?
C21 P1 C2 C3 -6.0(3) . . . . ?
C11 P1 C2 C3 145.8(3) . . . . ?
C1 P1 C2 C3 -111.7(3) . . . . ?
C21 P1 C2 C1 105.7(2) . . . . ?
C11 P1 C2 C1 -102.5(2) . . . . ?
C1 C2 C3 B1 95.1(4) . . . . ?
P1 C2 C3 B1 170.1(2) . . . . ?
C2 C1 C4 O1 -156.0(3) . . . . ?
P1 C1 C4 O1 -80.3(4) . . . . ?
C1 C4 O1 Si1 -111.1(3) . . . . ?
C4 O1 Si1 C6 -161.0(3) . . . . ?
C4 O1 Si1 C7 79.8(4) . . . . ?
C4 O1 Si1 C5 -41.2(4) . . . . ?
C21 P1 C11 C16 118.3(3) . . . . ?
C1 P1 C11 C16 -90.3(3) . . . . ?
C2 P1 C11 C16 -31.8(4) . . . . ?
C21 P1 C11 C12 -59.2(4) . . . . ?
C1 P1 C11 C12 92.2(3) . . . . ?
C2 P1 C11 C12 150.8(3) . . . . ?
C16 C11 C12 C13 -2.7(6) . . . . ?
P1 C11 C12 C13 174.8(3) . . . . ?
C16 C11 C12 C17 176.3(4) . . . . ?
P1 C11 C12 C17 -6.2(5) . . . . ?
C11 C12 C13 C14 1.5(6) . . . . ?
C17 C12 C13 C14 -177.5(4) . . . . ?
C12 C13 C14 C15 0.9(7) . . . . ?
C12 C13 C14 C18 -178.5(5) . . . . ?
C13 C14 C15 C16 -2.3(7) . . . . ?
C18 C14 C15 C16 177.1(5) . . . . ?
C14 C15 C16 C11 1.1(6) . . . . ?
C14 C15 C16 C19 180.0(4) . . . . ?
C12 C11 C16 C15 1.5(5) . . . . ?
P1 C11 C16 C15 -175.9(3) . . . . ?
C12 C11 C16 C19 -177.3(4) . . . . ?
P1 C11 C16 C19 5.3(5) . . . . ?
C11 P1 C21 C22 -70.2(3) . . . . ?
C1 P1 C21 C22 137.5(3) . . . . ?
C2 P1 C21 C22 82.7(3) . . . . ?
C11 P1 C21 C26 113.7(3) . . . . ?
C1 P1 C21 C26 -38.7(4) . . . . ?
C2 P1 C21 C26 -93.5(3) . . . . ?
C26 C21 C22 C23 0.0(6) . . . . ?
P1 C21 C22 C23 -176.3(3) . . . . ?
C26 C21 C22 C27 -179.9(4) . . . . ?
P1 C21 C22 C27 3.9(5) . . . . ?
C21 C22 C23 C24 1.4(6) . . . . ?
C27 C22 C23 C24 -178.8(4) . . . . ?
C22 C23 C24 C25 -2.6(6) . . . . ?
C22 C23 C24 C28 177.0(4) . . . . ?
C23 C24 C25 C26 2.5(7) . . . . ?
C28 C24 C25 C26 -177.1(4) . . . . ?
C24 C25 C26 C21 -1.3(7) . . . . ?
C24 C25 C26 C29 177.5(4) . . . . ?
C22 C21 C26 C25 0.0(6) . . . . ?
P1 C21 C26 C25 176.0(3) . . . . ?
C22 C21 C26 C29 -178.7(4) . . . . ?
P1 C21 C26 C29 -2.7(6) . . . . ?
C2 C3 B1 C51 -53.8(4) . . . . ?
C2 C3 B1 C41 70.1(4) . . . . ?
C2 C3 B1 C31 -175.3(3) . . . . ?
C3 B1 C31 C32 134.9(4) . . . . ?
C51 B1 C31 C32 18.5(5) . . . . ?
C41 B1 C31 C32 -102.6(4) . . . . ?
C3 B1 C31 C36 -51.1(4) . . . . ?
C51 B1 C31 C36 -167.6(3) . . . . ?
C41 B1 C31 C36 71.3(4) . . . . ?
C36 C31 C32 F32 -176.4(3) . . . . ?
B1 C31 C32 F32 -2.1(5) . . . . ?
C36 C31 C32 C33 1.7(5) . . . . ?
B1 C31 C32 C33 176.0(3) . . . . ?
F32 C32 C33 F33 -2.1(5) . . . . ?
C31 C32 C33 F33 179.7(3) . . . . ?
F32 C32 C33 C34 177.8(3) . . . . ?
C31 C32 C33 C34 -0.5(6) . . . . ?
F33 C33 C34 F34 1.1(6) . . . . ?
C32 C33 C34 F34 -178.8(3) . . . . ?
F33 C33 C34 C35 179.2(4) . . . . ?
C32 C33 C34 C35 -0.7(6) . . . . ?
F34 C34 C35 F35 0.6(6) . . . . ?
C33 C34 C35 F35 -177.6(4) . . . . ?
F34 C34 C35 C36 178.6(3) . . . . ?
C33 C34 C35 C36 0.5(6) . . . . ?
F35 C35 C36 F36 0.6(5) . . . . ?
C34 C35 C36 F36 -177.4(3) . . . . ?
F35 C35 C36 C31 179.0(3) . . . . ?
C34 C35 C36 C31 0.9(6) . . . . ?
C32 C31 C36 F36 176.4(3) . . . . ?
B1 C31 C36 F36 1.6(5) . . . . ?
C32 C31 C36 C35 -1.9(5) . . . . ?
B1 C31 C36 C35 -176.7(3) . . . . ?
C3 B1 C41 C46 12.7(5) . . . . ?
C51 B1 C41 C46 132.5(4) . . . . ?
C31 B1 C41 C46 -106.1(4) . . . . ?
C3 B1 C41 C42 -172.6(3) . . . . ?
C51 B1 C41 C42 -52.8(4) . . . . ?
C31 B1 C41 C42 68.6(4) . . . . ?
C46 C41 C42 F42 -179.5(3) . . . . ?
B1 C41 C42 F42 5.1(5) . . . . ?
C46 C41 C42 C43 1.5(5) . . . . ?
B1 C41 C42 C43 -173.9(3) . . . . ?
F42 C42 C43 F43 1.7(5) . . . . ?
C41 C42 C43 F43 -179.2(3) . . . . ?
F42 C42 C43 C44 -179.3(3) . . . . ?
C41 C42 C43 C44 -0.2(6) . . . . ?
F43 C43 C44 F44 -0.7(6) . . . . ?
C42 C43 C44 F44 -179.7(3) . . . . ?
F43 C43 C44 C45 177.9(4) . . . . ?
C42 C43 C44 C45 -1.1(6) . . . . ?
F44 C44 C45 F45 0.2(6) . . . . ?
C43 C44 C45 F45 -178.5(4) . . . . ?
F44 C44 C45 C46 179.5(4) . . . . ?
C43 C44 C45 C46 0.9(6) . . . . ?
C42 C41 C46 F46 179.5(3) . . . . ?
B1 C41 C46 F46 -5.4(5) . . . . ?
C42 C41 C46 C45 -1.7(5) . . . . ?
B1 C41 C46 C45 173.4(3) . . . . ?
F45 C45 C46 F46 -1.2(5) . . . . ?
C44 C45 C46 F46 179.4(3) . . . . ?
F45 C45 C46 C41 179.9(3) . . . . ?
C44 C45 C46 C41 0.6(6) . . . . ?
C3 B1 C51 C56 -69.2(4) . . . . ?
C41 B1 C51 C56 165.2(3) . . . . ?
C31 B1 C51 C56 50.0(4) . . . . ?
C3 B1 C51 C52 102.9(4) . . . . ?
C41 B1 C51 C52 -22.7(5) . . . . ?
C31 B1 C51 C52 -137.9(3) . . . . ?
C56 C51 C52 F52 174.2(3) . . . . ?
B1 C51 C52 F52 1.5(5) . . . . ?
C56 C51 C52 C53 -3.2(5) . . . . ?
B1 C51 C52 C53 -176.0(3) . . . . ?
F52 C52 C53 F53 3.2(5) . . . . ?
C51 C52 C53 F53 -179.2(3) . . . . ?
F52 C52 C53 C54 -176.5(3) . . . . ?
C51 C52 C53 C54 1.1(6) . . . . ?
F53 C53 C54 F54 1.0(6) . . . . ?
C52 C53 C54 F54 -179.3(3) . . . . ?
F53 C53 C54 C55 -178.7(4) . . . . ?
C52 C53 C54 C55 1.0(6) . . . . ?
F54 C54 C55 F55 0.3(6) . . . . ?
C53 C54 C55 F55 179.9(4) . . . . ?
F54 C54 C55 C56 179.7(4) . . . . ?
C53 C54 C55 C56 -0.7(6) . . . . ?
F55 C55 C56 F56 -1.4(6) . . . . ?
C54 C55 C56 F56 179.2(4) . . . . ?
F55 C55 C56 C51 177.5(4) . . . . ?
C54 C55 C56 C51 -1.9(6) . . . . ?
C52 C51 C56 F56 -177.5(3) . . . . ?
B1 C51 C56 F56 -4.4(5) . . . . ?
C52 C51 C56 C55 3.6(6) . . . . ?
B1 C51 C56 C55 176.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_erk7976
_database_code_depnum_ccdc_archive 'CCDC 1419595'
_audit_update_record             
;
2015-08-19 deposited with the CCDC.
2015-12-23 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H6 B F15 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         618.11

_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                   9.4516(4)
_cell_length_b                   12.1427(5)
_cell_length_c                   12.2399(4)
_cell_angle_alpha                110.4140(10)
_cell_angle_beta                 100.0700(10)
_cell_angle_gamma                97.1110(10)
_cell_volume                     1269.99(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9800
_cell_measurement_theta_min      2.5324
_cell_measurement_theta_max      27.5170
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.113
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608

_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.95
_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 10.4167

_diffrn_reflns_number            51651
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         27.61
_diffrn_reflns_theta_full        27.61
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             5853
_reflns_number_gt                4788
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0979
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_number_reflns         5853
_refine_ls_number_parameters     379
_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)+(0.0465P)²+0.6325P] 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         0.373
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.500 0.000 163.6 21.3
_platon_squeeze_details          
;
 A badly disordered half toluene molecule was found in the asymmetrical unit 
 and could not be satisfactorily refined. The program SQUEEZE (A. L. Spek
 J. Appl. Cryst., 2003, 36, 7-13) was therefore used to remove mathematically
 the effect of the solvent. 
 The quoted formula and derived parameters are not included the squeezed
 solvent molecule.
;

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (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
B B1 0.42516(17) 0.26233(13) 0.58031(14) 0.0135(3) Uani d . . . 1 . .
C C1 0.43946(15) 0.47859(12) 0.71172(12) 0.0148(3) Uani d . . . 1 . .
H H1 0.5337 0.4781 0.7539 0.018 Uiso calc U . R 1 . .
O O1 0.37180(10) 0.38676(8) 0.62391(9) 0.0136(2) Uani d . . . 1 . .
C C2 0.37989(15) 0.58532(12) 0.75141(12) 0.0148(3) Uani d . . . 1 . .
C C3 0.45653(16) 0.67822(13) 0.85909(14) 0.0192(3) Uani d . . . 1 . .
H H3 0.5468 0.6712 0.9019 0.023 Uiso calc U . R 1 . .
C C4 0.39951(18) 0.78032(13) 0.90266(14) 0.0227(3) Uani d . . . 1 . .
H H4 0.4497 0.8433 0.9763 0.027 Uiso calc U . R 1 . .
C C5 0.26861(18) 0.79025(13) 0.83819(15) 0.0223(3) Uani d . . . 1 . .
H H5 0.2297 0.8604 0.8682 0.027 Uiso calc U . R 1 . .
C C6 0.19350(17) 0.69853(14) 0.72994(14) 0.0216(3) Uani d . . . 1 . .
H H6 0.105 0.7071 0.6861 0.026 Uiso calc U . R 1 . .
C C7 0.24774(15) 0.59510(13) 0.68645(13) 0.0168(3) Uani d . . . 1 . .
H H7 0.1961 0.5316 0.6136 0.02 Uiso calc U . R 1 . .
C C11 0.32828(15) 0.18070(12) 0.63312(13) 0.0143(3) Uani d . . . 1 . .
C C12 0.23702(15) 0.06945(12) 0.56601(13) 0.0160(3) Uani d . . . 1 . .
F F12 0.22559(10) 0.01567(8) 0.44726(8) 0.0231(2) Uani d . . . 1 . .
C C13 0.15355(15) 0.00485(12) 0.61430(14) 0.0177(3) Uani d . . . 1 . .
F F13 0.06930(10) -0.10343(8) 0.54384(9) 0.0258(2) Uani d . . . 1 . .
C C14 0.15668(16) 0.05115(13) 0.73456(14) 0.0185(3) Uani d . . . 1 . .
F F14 0.07541(10) -0.00997(9) 0.78233(9) 0.0264(2) Uani d . . . 1 . .
C C15 0.24605(16) 0.16092(14) 0.80611(13) 0.0193(3) Uani d . . . 1 . .
F F15 0.25196(11) 0.20690(9) 0.92371(8) 0.0314(2) Uani d . . . 1 . .
C C16 0.32905(15) 0.22128(12) 0.75465(13) 0.0164(3) Uani d . . . 1 . .
F F16 0.41797(10) 0.32727(8) 0.83064(8) 0.0224(2) Uani d . . . 1 . .
C C21 0.60287(15) 0.28962(12) 0.63051(12) 0.0134(3) Uani d . . . 1 . .
C C22 0.69130(15) 0.37024(12) 0.60073(12) 0.0153(3) Uani d . . . 1 . .
F F22 0.62749(9) 0.43473(8) 0.54245(8) 0.02056(19) Uani d . . . 1 . .
C C23 0.84260(16) 0.39003(13) 0.62716(14) 0.0188(3) Uani d . . . 1 . .
F F23 0.92045(10) 0.46903(9) 0.59485(9) 0.0278(2) Uani d . . . 1 . .
C C24 0.91416(15) 0.32811(13) 0.68738(13) 0.0189(3) Uani d . . . 1 . .
F F24 1.06066(9) 0.34495(9) 0.71226(9) 0.0266(2) Uani d . . . 1 . .
C C25 0.83262(16) 0.24864(13) 0.72124(13) 0.0167(3) Uani d . . . 1 . .
F F25 0.90020(10) 0.18796(8) 0.78002(8) 0.0237(2) Uani d . . . 1 . .
C C26 0.68077(15) 0.23128(12) 0.69257(13) 0.0153(3) Uani d . . . 1 . .
F F26 0.60987(9) 0.15061(8) 0.72712(8) 0.0219(2) Uani d . . . 1 . .
C C31 0.38042(15) 0.21358(12) 0.43410(12) 0.0141(3) Uani d . . . 1 . .
C C32 0.25766(15) 0.23410(13) 0.36810(13) 0.0163(3) Uani d . . . 1 . .
F F32 0.16883(9) 0.30132(8) 0.42405(8) 0.0232(2) Uani d . . . 1 . .
C C33 0.21522(16) 0.18496(13) 0.24409(13) 0.0189(3) Uani d . . . 1 . .
F F33 0.09590(11) 0.20904(9) 0.18585(8) 0.0283(2) Uani d . . . 1 . .
C C34 0.29471(17) 0.10894(13) 0.17992(13) 0.0194(3) Uani d . . . 1 . .
F F34 0.25360(11) 0.05851(9) 0.05982(8) 0.0289(2) Uani d . . . 1 . .
C C35 0.41659(17) 0.08538(12) 0.24051(13) 0.0179(3) Uani d . . . 1 . .
F F35 0.49488(10) 0.01150(8) 0.17927(8) 0.0236(2) Uani d . . . 1 . .
C C36 0.45657(15) 0.13711(12) 0.36406(13) 0.0159(3) Uani d . . . 1 . .
F F36 0.57397(10) 0.10530(8) 0.41666(8) 0.0240(2) Uani d . . . 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
B1 O1 . 1.5945(17) ?
B1 C31 . 1.633(2) ?
B1 C21 . 1.633(2) ?
B1 C11 . 1.633(2) ?
C1 O1 . 1.2468(17) ?
C1 C2 . 1.4387(19) ?
C1 H1 . 0.95 ?
C2 C3 . 1.400(2) ?
C2 C7 . 1.401(2) ?
C3 C4 . 1.384(2) ?
C3 H3 . 0.95 ?
C4 C5 . 1.389(2) ?
C4 H4 . 0.95 ?
C5 C6 . 1.395(2) ?
C5 H5 . 0.95 ?
C6 C7 . 1.383(2) ?
C6 H6 . 0.95 ?
C7 H7 . 0.95 ?
C11 C12 . 1.390(2) ?
C11 C16 . 1.393(2) ?
C12 F12 . 1.3477(17) ?
C12 C13 . 1.386(2) ?
C13 F13 . 1.3477(17) ?
C13 C14 . 1.374(2) ?
C14 F14 . 1.3421(16) ?
C14 C15 . 1.380(2) ?
C15 F15 . 1.3380(17) ?
C15 C16 . 1.379(2) ?
C16 F16 . 1.3606(16) ?
C21 C26 . 1.3892(19) ?
C21 C22 . 1.3938(19) ?
C22 F22 . 1.3571(16) ?
C22 C23 . 1.381(2) ?
C23 F23 . 1.3452(17) ?
C23 C24 . 1.380(2) ?
C24 F24 . 1.3383(16) ?
C24 C25 . 1.380(2) ?
C25 F25 . 1.3395(16) ?
C25 C26 . 1.387(2) ?
C26 F26 . 1.3465(16) ?
C31 C36 . 1.3932(19) ?
C31 C32 . 1.3946(19) ?
C32 F32 . 1.3494(16) ?
C32 C33 . 1.385(2) ?
C33 F33 . 1.3458(17) ?
C33 C34 . 1.381(2) ?
C34 F34 . 1.3417(17) ?
C34 C35 . 1.375(2) ?
C35 F35 . 1.3429(16) ?
C35 C36 . 1.380(2) ?
C36 F36 . 1.3508(16) ?

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
O1 B1 C31 . . 104.66(10) ?
O1 B1 C21 . . 107.89(10) ?
C31 B1 C21 . . 111.12(11) ?
O1 B1 C11 . . 103.21(10) ?
C31 B1 C11 . . 112.62(11) ?
C21 B1 C11 . . 116.23(11) ?
O1 C1 C2 . . 122.31(13) ?
O1 C1 H1 . . 118.8 ?
C2 C1 H1 . . 118.8 ?
C1 O1 B1 . . 125.23(11) ?
C3 C2 C7 . . 120.93(13) ?
C3 C2 C1 . . 117.75(13) ?
C7 C2 C1 . . 121.30(13) ?
C4 C3 C2 . . 119.41(14) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C3 C4 C5 . . 119.71(14) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C4 C5 C6 . . 120.87(14) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C7 C6 C5 . . 120.05(14) ?
C7 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C6 C7 C2 . . 119.01(13) ?
C6 C7 H7 . . 120.5 ?
C2 C7 H7 . . 120.5 ?
C12 C11 C16 . . 113.51(13) ?
C12 C11 B1 . . 125.70(12) ?
C16 C11 B1 . . 120.77(12) ?
F12 C12 C13 . . 114.97(12) ?
F12 C12 C11 . . 121.35(13) ?
C13 C12 C11 . . 123.68(13) ?
F13 C13 C14 . . 119.74(13) ?
F13 C13 C12 . . 120.31(13) ?
C14 C13 C12 . . 119.95(13) ?
F14 C14 C13 . . 120.58(13) ?
F14 C14 C15 . . 120.33(14) ?
C13 C14 C15 . . 119.09(13) ?
F15 C15 C16 . . 120.96(14) ?
F15 C15 C14 . . 120.00(13) ?
C16 C15 C14 . . 119.03(14) ?
F16 C16 C15 . . 116.10(13) ?
F16 C16 C11 . . 119.18(12) ?
C15 C16 C11 . . 124.71(13) ?
C26 C21 C22 . . 113.90(12) ?
C26 C21 B1 . . 126.44(12) ?
C22 C21 B1 . . 119.35(12) ?
F22 C22 C23 . . 116.70(13) ?
F22 C22 C21 . . 119.22(12) ?
C23 C22 C21 . . 124.08(13) ?
F23 C23 C24 . . 119.90(13) ?
F23 C23 C22 . . 120.59(13) ?
C24 C23 C22 . . 119.51(13) ?
F24 C24 C25 . . 120.60(13) ?
F24 C24 C23 . . 120.30(14) ?
C25 C24 C23 . . 119.10(13) ?
F25 C25 C24 . . 119.94(13) ?
F25 C25 C26 . . 120.59(13) ?
C24 C25 C26 . . 119.46(13) ?
F26 C26 C25 . . 115.51(12) ?
F26 C26 C21 . . 120.55(12) ?
C25 C26 C21 . . 123.93(13) ?
C36 C31 C32 . . 113.95(13) ?
C36 C31 B1 . . 121.50(12) ?
C32 C31 B1 . . 124.29(12) ?
F32 C32 C33 . . 115.74(12) ?
F32 C32 C31 . . 120.61(13) ?
C33 C32 C31 . . 123.61(13) ?
F33 C33 C34 . . 119.82(13) ?
F33 C33 C32 . . 120.59(13) ?
C34 C33 C32 . . 119.57(13) ?
F34 C34 C35 . . 120.31(14) ?
F34 C34 C33 . . 120.46(14) ?
C35 C34 C33 . . 119.22(13) ?
F35 C35 C34 . . 119.88(13) ?
F35 C35 C36 . . 120.55(13) ?
C34 C35 C36 . . 119.56(13) ?
F36 C36 C35 . . 115.72(12) ?
F36 C36 C31 . . 120.17(12) ?
C35 C36 C31 . . 124.06(13) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 C1 O1 B1 . . . . -175.35(12) ?
C31 B1 O1 C1 . . . . -141.21(13) ?
C21 B1 O1 C1 . . . . -22.79(17) ?
C11 B1 O1 C1 . . . . 100.77(14) ?
O1 C1 C2 C3 . . . . 172.53(13) ?
O1 C1 C2 C7 . . . . -5.8(2) ?
C7 C2 C3 C4 . . . . 1.0(2) ?
C1 C2 C3 C4 . . . . -177.39(14) ?
C2 C3 C4 C5 . . . . -1.1(2) ?
C3 C4 C5 C6 . . . . 0.1(2) ?
C4 C5 C6 C7 . . . . 1.1(2) ?
C5 C6 C7 C2 . . . . -1.2(2) ?
C3 C2 C7 C6 . . . . 0.2(2) ?
C1 C2 C7 C6 . . . . 178.51(13) ?
O1 B1 C11 C12 . . . . 123.97(13) ?
C31 B1 C11 C12 . . . . 11.67(18) ?
C21 B1 C11 C12 . . . . -118.16(15) ?
O1 B1 C11 C16 . . . . -54.50(15) ?
C31 B1 C11 C16 . . . . -166.81(12) ?
C21 B1 C11 C16 . . . . 63.37(17) ?
C16 C11 C12 F12 . . . . -178.55(12) ?
B1 C11 C12 F12 . . . . 2.9(2) ?
C16 C11 C12 C13 . . . . 0.5(2) ?
B1 C11 C12 C13 . . . . -178.10(13) ?
F12 C12 C13 F13 . . . . 0.13(19) ?
C11 C12 C13 F13 . . . . -178.95(13) ?
F12 C12 C13 C14 . . . . -179.96(12) ?
C11 C12 C13 C14 . . . . 1.0(2) ?
F13 C13 C14 F14 . . . . -0.7(2) ?
C12 C13 C14 F14 . . . . 179.41(12) ?
F13 C13 C14 C15 . . . . 178.53(13) ?
C12 C13 C14 C15 . . . . -1.4(2) ?
F14 C14 C15 F15 . . . . 0.0(2) ?
C13 C14 C15 F15 . . . . -179.21(13) ?
F14 C14 C15 C16 . . . . 179.57(13) ?
C13 C14 C15 C16 . . . . 0.4(2) ?
F15 C15 C16 F16 . . . . 1.4(2) ?
C14 C15 C16 F16 . . . . -178.14(13) ?
F15 C15 C16 C11 . . . . -179.22(13) ?
C14 C15 C16 C11 . . . . 1.2(2) ?
C12 C11 C16 F16 . . . . 177.76(12) ?
B1 C11 C16 F16 . . . . -3.59(19) ?
C12 C11 C16 C15 . . . . -1.6(2) ?
B1 C11 C16 C15 . . . . 177.08(13) ?
O1 B1 C21 C26 . . . . 129.74(13) ?
C31 B1 C21 C26 . . . . -116.06(15) ?
C11 B1 C21 C26 . . . . 14.48(19) ?
O1 B1 C21 C22 . . . . -57.06(16) ?
C31 B1 C21 C22 . . . . 57.13(16) ?
C11 B1 C21 C22 . . . . -172.33(12) ?
C26 C21 C22 F22 . . . . -178.43(12) ?
B1 C21 C22 F22 . . . . 7.55(19) ?
C26 C21 C22 C23 . . . . 1.3(2) ?
B1 C21 C22 C23 . . . . -172.67(13) ?
F22 C22 C23 F23 . . . . -0.6(2) ?
C21 C22 C23 F23 . . . . 179.66(13) ?
F22 C22 C23 C24 . . . . 179.37(13) ?
C21 C22 C23 C24 . . . . -0.4(2) ?
F23 C23 C24 F24 . . . . -1.0(2) ?
C22 C23 C24 F24 . . . . 179.08(13) ?
F23 C23 C24 C25 . . . . 179.13(13) ?
C22 C23 C24 C25 . . . . -0.8(2) ?
F24 C24 C25 F25 . . . . 0.3(2) ?
C23 C24 C25 F25 . . . . -179.83(13) ?
F24 C24 C25 C26 . . . . -178.91(13) ?
C23 C24 C25 C26 . . . . 1.0(2) ?
F25 C25 C26 F26 . . . . -0.34(19) ?
C24 C25 C26 F26 . . . . 178.84(12) ?
F25 C25 C26 C21 . . . . -179.13(13) ?
C24 C25 C26 C21 . . . . 0.1(2) ?
C22 C21 C26 F26 . . . . -179.89(12) ?
B1 C21 C26 F26 . . . . -6.4(2) ?
C22 C21 C26 C25 . . . . -1.2(2) ?
B1 C21 C26 C25 . . . . 172.36(13) ?
O1 B1 C31 C36 . . . . 153.54(12) ?
C21 B1 C31 C36 . . . . 37.34(17) ?
C11 B1 C31 C36 . . . . -95.06(15) ?
O1 B1 C31 C32 . . . . -32.65(17) ?
C21 B1 C31 C32 . . . . -148.85(13) ?
C11 B1 C31 C32 . . . . 78.75(16) ?
C36 C31 C32 F32 . . . . 176.53(12) ?
B1 C31 C32 F32 . . . . 2.3(2) ?
C36 C31 C32 C33 . . . . -0.9(2) ?
B1 C31 C32 C33 . . . . -175.14(13) ?
F32 C32 C33 F33 . . . . 2.8(2) ?
C31 C32 C33 F33 . . . . -179.59(13) ?
F32 C32 C33 C34 . . . . -176.01(13) ?
C31 C32 C33 C34 . . . . 1.6(2) ?
F33 C33 C34 F34 . . . . -0.2(2) ?
C32 C33 C34 F34 . . . . 178.65(13) ?
F33 C33 C34 C35 . . . . 179.82(13) ?
C32 C33 C34 C35 . . . . -1.3(2) ?
F34 C34 C35 F35 . . . . 0.0(2) ?
C33 C34 C35 F35 . . . . 179.93(13) ?
F34 C34 C35 C36 . . . . -179.41(13) ?
C33 C34 C35 C36 . . . . 0.6(2) ?
F35 C35 C36 F36 . . . . -2.0(2) ?
C34 C35 C36 F36 . . . . 177.34(13) ?
F35 C35 C36 C31 . . . . -179.31(13) ?
C34 C35 C36 C31 . . . . 0.1(2) ?
C32 C31 C36 F36 . . . . -177.07(12) ?
B1 C31 C36 F36 . . . . -2.7(2) ?
C32 C31 C36 C35 . . . . 0.1(2) ?
B1 C31 C36 C35 . . . . 174.50(13) ?

