####################################################################### 
# 
# 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_mh031_0m
_audit_block_doi                 10.5517/cc13ytnj
_database_code_depnum_ccdc_archive 'CCDC 1041558'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5SC00051C 2015
_audit_update_record             
;
2014-12-30 deposited with the CCDC.
2015-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H26 F4 P2'
_chemical_formula_sum            'C34 H26 F4 P2'
_chemical_formula_weight         572.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   9.2062(7)
_cell_length_b                   16.7452(12)
_cell_length_c                   17.6319(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.286(3)
_cell_angle_gamma                90.00
_cell_volume                     2665.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    149(2)
_cell_measurement_reflns_used    4799
_cell_measurement_theta_min      5.261
_cell_measurement_theta_max      53.808

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7198
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
'SADABS. Area-Detector Integration Software. (Siemens Industrial Automation, 1995, Inc.: Madison, WI)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      149(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24302
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         27.55
_reflns_number_total             6136
_reflns_number_gt                3558
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'Bruker SMART. Area-Detector Software Package. (Siemens Industrial Automation, 1993, Inc.: Madison, WI)'
_computing_cell_refinement       
'Bruker SMART. Area-Detector Software Package. (Siemens Industrial Automation, 1993, Inc.: Madison, WI)'
_computing_data_reduction        
'Bruker SAINT. Area-Detector Integration Software. (Siemens Industrial Automation, 1995, Inc.: Madison, WI)'
_computing_structure_solution    
'SHELX-97. Programs for Crystal Structure Analysis. (G. M. Sheldrick, 1997, Release 97-2, University of Gttingen, Germany)'
_computing_structure_refinement  
'SHELX-97. Programs for Crystal Structure Analysis. (G. M. Sheldrick, 1997, Release 97-2, University of Gttingen, Germany)'
_computing_molecular_graphics    
'Ortep for Windows (L. J. Farrugia, J. Appl. Cryst. 1997, 30, 565)'
_computing_publication_material  
'WinGX v1.70.01 (L. J. Farrugia, J. Appl. Cryst. 1999, 32, 837)'

_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)+(0.0766P)²+0.4159P] 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         6136
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1615
_refine_ls_wR_factor_gt          0.1335
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0044(3) 0.54292(19) 0.19938(18) 0.0240(7) Uani 1 1 d . . .
C2 C 0.9757(4) 0.4836(2) 0.1461(2) 0.0363(9) Uani 1 1 d . . .
H2 H 0.9539 0.4983 0.0930 0.044 Uiso 1 1 calc R . .
C3 C 0.9760(4) 0.4015(2) 0.1644(2) 0.0411(10) Uani 1 1 d . . .
H3 H 0.9470 0.3625 0.1252 0.049 Uiso 1 1 calc R . .
C4 C 1.0183(4) 0.3806(2) 0.2381(2) 0.0397(9) Uani 1 1 d . . .
H4 H 1.0305 0.3255 0.2509 0.048 Uiso 1 1 calc R . .
C5 C 1.0457(4) 0.4384(2) 0.2985(2) 0.0317(8) Uani 1 1 d . . .
C6 C 1.0258(3) 0.52205(18) 0.28134(19) 0.0252(7) Uani 1 1 d . . .
C7 C 1.0294(3) 0.57311(19) 0.34920(18) 0.0252(7) Uani 1 1 d . . .
C8 C 1.0890(4) 0.5422(2) 0.42058(19) 0.0316(8) Uani 1 1 d . . .
H8 H 1.1033 0.5775 0.4636 0.038 Uiso 1 1 calc R . .
C9 C 1.1302(4) 0.4620(2) 0.4342(2) 0.0399(9) Uani 1 1 d . . .
H9 H 1.1801 0.4451 0.4840 0.048 Uiso 1 1 calc R . .
C10 C 1.0981(4) 0.4101(2) 0.3761(2) 0.0383(9) Uani 1 1 d . . .
H10 H 1.1097 0.3544 0.3859 0.046 Uiso 1 1 calc R . .
C11 C 1.2263(4) 0.62915(18) 0.12079(18) 0.0245(7) Uani 1 1 d . . .
C12 C 1.3617(4) 0.6592(2) 0.1608(2) 0.0305(8) Uani 1 1 d . . .
H12 H 1.3673 0.6826 0.2103 0.037 Uiso 1 1 calc R . .
C13 C 1.4870(4) 0.6550(2) 0.1291(2) 0.0444(10) Uani 1 1 d . . .
H13 H 1.5778 0.6759 0.1570 0.053 Uiso 1 1 calc R . .
C14 C 1.4820(4) 0.6209(2) 0.0573(2) 0.0436(10) Uani 1 1 d . . .
H14 H 1.5685 0.6189 0.0356 0.052 Uiso 1 1 calc R . .
C15 C 1.3510(5) 0.5901(2) 0.0176(2) 0.0419(10) Uani 1 1 d . . .
H15 H 1.3475 0.5657 -0.0313 0.050 Uiso 1 1 calc R . .
C16 C 1.2241(4) 0.5942(2) 0.04822(19) 0.0328(8) Uani 1 1 d . . .
H16 H 1.1341 0.5730 0.0197 0.039 Uiso 1 1 calc R . .
C17 C 0.9836(3) 0.73952(19) 0.14591(18) 0.0243(7) Uani 1 1 d . . .
C18 C 0.8375(4) 0.7532(2) 0.10891(18) 0.0292(8) Uani 1 1 d . . .
H18 H 0.7721 0.7093 0.0955 0.035 Uiso 1 1 calc R . .
C19 C 0.7871(4) 0.8296(2) 0.0917(2) 0.0374(9) Uani 1 1 d . . .
H19 H 0.6862 0.8387 0.0688 0.045 Uiso 1 1 calc R . .
C20 C 0.8835(4) 0.8931(2) 0.1077(2) 0.0394(9) Uani 1 1 d . . .
H20 H 0.8495 0.9457 0.0940 0.047 Uiso 1 1 calc R . .
C21 C 1.0273(4) 0.8810(2) 0.1431(2) 0.0381(9) Uani 1 1 d . . .
H21 H 1.0931 0.9250 0.1537 0.046 Uiso 1 1 calc R . .
C22 C 1.0778(4) 0.8044(2) 0.16377(19) 0.0306(8) Uani 1 1 d . . .
H22 H 1.1771 0.7964 0.1902 0.037 Uiso 1 1 calc R . .
C23 C 0.9785(4) 0.77060(19) 0.33650(18) 0.0268(7) Uani 1 1 d . . .
C24 C 0.8681(4) 0.82276(19) 0.30132(19) 0.0291(8) Uani 1 1 d . . .
H24 H 0.7740 0.8023 0.2774 0.035 Uiso 1 1 calc R . .
C25 C 0.8939(4) 0.9045(2) 0.3009(2) 0.0413(10) Uani 1 1 d . . .
H25 H 0.8170 0.9400 0.2784 0.050 Uiso 1 1 calc R . .
C26 C 1.0335(5) 0.9336(2) 0.3336(2) 0.0509(11) Uani 1 1 d . . .
H26 H 1.0531 0.9893 0.3329 0.061 Uiso 1 1 calc R . .
C27 C 1.1425(4) 0.8819(2) 0.3669(3) 0.0493(11) Uani 1 1 d . . .
H27 H 1.2384 0.9021 0.3879 0.059 Uiso 1 1 calc R . .
C28 C 1.1161(4) 0.8011(2) 0.3704(2) 0.0413(9) Uani 1 1 d . . .
H28 H 1.1918 0.7665 0.3960 0.050 Uiso 1 1 calc R . .
C29 C 0.7449(3) 0.65814(18) 0.37584(17) 0.0211(7) Uani 1 1 d . . .
C30 C 0.7073(4) 0.70423(19) 0.43487(18) 0.0267(7) Uani 1 1 d . . .
H30 H 0.7783 0.7392 0.4640 0.032 Uiso 1 1 calc R . .
C31 C 0.5656(4) 0.6991(2) 0.4512(2) 0.0385(9) Uani 1 1 d . . .
H31 H 0.5397 0.7313 0.4909 0.046 Uiso 1 1 calc R . .
C32 C 0.4628(4) 0.6476(2) 0.4101(2) 0.0420(10) Uani 1 1 d . . .
H32 H 0.3669 0.6436 0.4221 0.050 Uiso 1 1 calc R . .
C33 C 0.4990(4) 0.6018(2) 0.3516(2) 0.0409(9) Uani 1 1 d . . .
H33 H 0.4281 0.5662 0.3234 0.049 Uiso 1 1 calc R . .
C34 C 0.6375(4) 0.60754(19) 0.33399(19) 0.0290(8) Uani 1 1 d . . .
H34 H 0.6607 0.5766 0.2927 0.035 Uiso 1 1 calc R . .
F1 F 0.9507(2) 0.61673(11) 0.07470(10) 0.0319(5) Uani 1 1 d . . .
F2 F 1.15472(18) 0.66245(11) 0.24662(9) 0.0252(4) Uani 1 1 d . . .
F3 F 0.85086(18) 0.65692(10) 0.25771(9) 0.0252(4) Uani 1 1 d . . .
F4 F 1.0012(2) 0.68128(11) 0.44463(10) 0.0314(5) Uani 1 1 d . . .
P1 P 1.05834(9) 0.63830(5) 0.16025(5) 0.0224(2) Uani 1 1 d . . .
P2 P 0.92664(9) 0.66732(5) 0.35099(5) 0.0217(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.357(4) . ?
C1 C6 1.462(4) . ?
C1 P1 1.846(3) . ?
C2 C3 1.413(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.330(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.424(5) . ?
C4 H4 0.9500 . ?
C5 C10 1.439(5) . ?
C5 C6 1.438(4) . ?
C6 C7 1.466(4) . ?
C7 C8 1.372(4) . ?
C7 P2 1.843(3) . ?
C8 C9 1.404(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.333(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.400(4) . ?
C11 C16 1.404(4) . ?
C11 P1 1.822(3) . ?
C12 C13 1.377(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.371(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.387(4) . ?
C17 C18 1.395(4) . ?
C17 P1 1.828(3) . ?
C18 C19 1.376(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.377(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.364(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.389(5) . ?
C23 C24 1.391(4) . ?
C23 P2 1.825(3) . ?
C24 C25 1.389(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.368(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.378(5) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C34 1.398(4) . ?
C29 C30 1.393(4) . ?
C29 P2 1.817(3) . ?
C30 C31 1.392(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.377(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.377(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.373(5) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
F1 P1 1.6740(18) . ?
F2 P1 1.6556(17) . ?
F3 P2 1.6653(18) . ?
F4 P2 1.6756(18) . ?

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
C2 C1 C6 118.7(3) . . ?
C2 C1 P1 113.9(2) . . ?
C6 C1 P1 125.6(2) . . ?
C1 C2 C3 124.3(3) . . ?
C1 C2 H2 117.9 . . ?
C3 C2 H2 117.9 . . ?
C4 C3 C2 117.8(3) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 121.8(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C10 117.7(3) . . ?
C4 C5 C6 120.5(3) . . ?
C10 C5 C6 121.8(3) . . ?
C5 C6 C1 115.4(3) . . ?
C5 C6 C7 114.5(3) . . ?
C1 C6 C7 130.1(3) . . ?
C8 C7 C6 118.1(3) . . ?
C8 C7 P2 114.9(2) . . ?
C6 C7 P2 125.7(2) . . ?
C7 C8 C9 124.3(3) . . ?
C7 C8 H8 117.8 . . ?
C9 C8 H8 117.8 . . ?
C10 C9 C8 118.8(3) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C5 119.9(3) . . ?
C9 C10 H10 120.0 . . ?
C5 C10 H10 120.0 . . ?
C12 C11 C16 117.5(3) . . ?
C12 C11 P1 121.1(2) . . ?
C16 C11 P1 121.4(3) . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.8(4) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 119.4(4) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 121.0(3) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C22 C17 C18 118.8(3) . . ?
C22 C17 P1 119.5(2) . . ?
C18 C17 P1 121.3(2) . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.8(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 120.1(3) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C28 C23 C24 119.1(3) . . ?
C28 C23 P2 122.0(3) . . ?
C24 C23 P2 118.0(2) . . ?
C23 C24 C25 120.7(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 119.2(4) . . ?
C26 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C27 C26 C25 119.8(4) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C28 121.3(4) . . ?
C26 C27 H27 119.3 . . ?
C28 C27 H27 119.3 . . ?
C27 C28 C23 119.7(4) . . ?
C27 C28 H28 120.1 . . ?
C23 C28 H28 120.1 . . ?
C34 C29 C30 118.5(3) . . ?
C34 C29 P2 120.9(2) . . ?
C30 C29 P2 120.6(2) . . ?
C31 C30 C29 120.0(3) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C32 C31 C30 120.3(3) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C33 C32 C31 120.0(3) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C34 120.1(3) . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C33 C34 C29 121.0(3) . . ?
C33 C34 H34 119.5 . . ?
C29 C34 H34 119.5 . . ?
F2 P1 F1 176.08(10) . . ?
F2 P1 C11 91.70(12) . . ?
F1 P1 C11 91.98(12) . . ?
F2 P1 C17 91.15(12) . . ?
F1 P1 C17 86.28(12) . . ?
C11 P1 C17 110.46(14) . . ?
F2 P1 C1 90.14(12) . . ?
F1 P1 C1 89.73(12) . . ?
C11 P1 C1 112.35(14) . . ?
C17 P1 C1 137.11(15) . . ?
F3 P2 F4 177.93(10) . . ?
F3 P2 C29 90.10(12) . . ?
F4 P2 C29 89.61(12) . . ?
F3 P2 C23 91.79(12) . . ?
F4 P2 C23 86.44(12) . . ?
C29 P2 C23 113.10(14) . . ?
F3 P2 C7 90.62(12) . . ?
F4 P2 C7 91.35(12) . . ?
C29 P2 C7 115.57(14) . . ?
C23 P2 C7 131.25(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -5.1(5) . . . . ?
P1 C1 C2 C3 160.2(3) . . . . ?
C1 C2 C3 C4 -5.4(6) . . . . ?
C2 C3 C4 C5 7.4(6) . . . . ?
C3 C4 C5 C10 -177.0(3) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
C4 C5 C6 C1 -11.1(4) . . . . ?
C10 C5 C6 C1 166.9(3) . . . . ?
C4 C5 C6 C7 168.6(3) . . . . ?
C10 C5 C6 C7 -13.4(4) . . . . ?
C2 C1 C6 C5 12.9(4) . . . . ?
P1 C1 C6 C5 -150.6(2) . . . . ?
C2 C1 C6 C7 -166.8(3) . . . . ?
P1 C1 C6 C7 29.7(5) . . . . ?
C5 C6 C7 C8 17.1(4) . . . . ?
C1 C6 C7 C8 -163.2(3) . . . . ?
C5 C6 C7 P2 -149.0(3) . . . . ?
C1 C6 C7 P2 30.7(5) . . . . ?
C6 C7 C8 C9 -8.2(5) . . . . ?
P2 C7 C8 C9 159.4(3) . . . . ?
C7 C8 C9 C10 -6.4(6) . . . . ?
C8 C9 C10 C5 10.5(5) . . . . ?
C4 C5 C10 C9 177.7(3) . . . . ?
C6 C5 C10 C9 -0.3(5) . . . . ?
C16 C11 C12 C13 0.7(5) . . . . ?
P1 C11 C12 C13 -177.2(3) . . . . ?
C11 C12 C13 C14 -0.2(6) . . . . ?
C12 C13 C14 C15 -0.8(6) . . . . ?
C13 C14 C15 C16 1.2(6) . . . . ?
C14 C15 C16 C11 -0.7(6) . . . . ?
C12 C11 C16 C15 -0.3(5) . . . . ?
P1 C11 C16 C15 177.7(3) . . . . ?
C22 C17 C18 C19 -1.1(5) . . . . ?
P1 C17 C18 C19 -173.5(3) . . . . ?
C17 C18 C19 C20 3.1(5) . . . . ?
C18 C19 C20 C21 -2.4(6) . . . . ?
C19 C20 C21 C22 -0.4(6) . . . . ?
C18 C17 C22 C21 -1.6(5) . . . . ?
P1 C17 C22 C21 170.9(3) . . . . ?
C20 C21 C22 C17 2.4(5) . . . . ?
C28 C23 C24 C25 -0.8(5) . . . . ?
P2 C23 C24 C25 168.6(3) . . . . ?
C23 C24 C25 C26 2.3(5) . . . . ?
C24 C25 C26 C27 -1.1(6) . . . . ?
C25 C26 C27 C28 -1.7(6) . . . . ?
C26 C27 C28 C23 3.1(6) . . . . ?
C24 C23 C28 C27 -1.9(5) . . . . ?
P2 C23 C28 C27 -170.8(3) . . . . ?
C34 C29 C30 C31 0.2(5) . . . . ?
P2 C29 C30 C31 177.3(2) . . . . ?
C29 C30 C31 C32 1.1(5) . . . . ?
C30 C31 C32 C33 -1.1(5) . . . . ?
C31 C32 C33 C34 -0.2(6) . . . . ?
C32 C33 C34 C29 1.5(5) . . . . ?
C30 C29 C34 C33 -1.5(5) . . . . ?
P2 C29 C34 C33 -178.6(3) . . . . ?
C12 C11 P1 F2 -14.1(3) . . . . ?
C16 C11 P1 F2 168.0(3) . . . . ?
C12 C11 P1 F1 164.5(3) . . . . ?
C16 C11 P1 F1 -13.4(3) . . . . ?
C12 C11 P1 C17 77.8(3) . . . . ?
C16 C11 P1 C17 -100.1(3) . . . . ?
C12 C11 P1 C1 -104.9(3) . . . . ?
C16 C11 P1 C1 77.2(3) . . . . ?
C22 C17 P1 F2 45.6(3) . . . . ?
C18 C17 P1 F2 -142.1(3) . . . . ?
C22 C17 P1 F1 -137.4(3) . . . . ?
C18 C17 P1 F1 34.9(3) . . . . ?
C22 C17 P1 C11 -46.7(3) . . . . ?
C18 C17 P1 C11 125.7(3) . . . . ?
C22 C17 P1 C1 137.0(3) . . . . ?
C18 C17 P1 C1 -50.6(4) . . . . ?
C2 C1 P1 F2 -152.5(3) . . . . ?
C6 C1 P1 F2 11.6(3) . . . . ?
C2 C1 P1 F1 31.4(3) . . . . ?
C6 C1 P1 F1 -164.4(3) . . . . ?
C2 C1 P1 C11 -60.7(3) . . . . ?
C6 C1 P1 C11 103.5(3) . . . . ?
C2 C1 P1 C17 115.6(3) . . . . ?
C6 C1 P1 C17 -80.2(3) . . . . ?
C34 C29 P2 F3 35.1(3) . . . . ?
C30 C29 P2 F3 -141.9(2) . . . . ?
C34 C29 P2 F4 -146.9(3) . . . . ?
C30 C29 P2 F4 36.0(3) . . . . ?
C34 C29 P2 C23 127.1(3) . . . . ?
C30 C29 P2 C23 -49.9(3) . . . . ?
C34 C29 P2 C7 -55.6(3) . . . . ?
C30 C29 P2 C7 127.3(3) . . . . ?
C28 C23 P2 F3 -136.8(3) . . . . ?
C24 C23 P2 F3 54.1(3) . . . . ?
C28 C23 P2 F4 44.2(3) . . . . ?
C24 C23 P2 F4 -124.9(3) . . . . ?
C28 C23 P2 C29 132.3(3) . . . . ?
C24 C23 P2 C29 -36.8(3) . . . . ?
C28 C23 P2 C7 -44.4(4) . . . . ?
C24 C23 P2 C7 146.5(2) . . . . ?
C8 C7 P2 F3 -165.3(3) . . . . ?
C6 C7 P2 F3 1.2(3) . . . . ?
C8 C7 P2 F4 15.3(3) . . . . ?
C6 C7 P2 F4 -178.2(3) . . . . ?
C8 C7 P2 C29 -74.9(3) . . . . ?
C6 C7 P2 C29 91.6(3) . . . . ?
C8 C7 P2 C23 101.8(3) . . . . ?
C6 C7 P2 C23 -91.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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_rh004_0m
_audit_block_doi                 10.5517/cc13ytpk
_database_code_depnum_ccdc_archive 'CCDC 1041559'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5SC00051C 2015
_audit_update_record             
;
2014-12-30 deposited with the CCDC.
2015-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 F4 P2'
_chemical_formula_sum            'C25 H22 F4 P2'
_chemical_formula_weight         460.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2'
_symmetry_space_group_name_Hall  'C 2y'

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

_cell_length_a                   21.0973(18)
_cell_length_b                   8.3882(7)
_cell_length_c                   6.3567(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.383(3)
_cell_angle_gamma                90.00
_cell_volume                     1098.76(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5976
_cell_measurement_theta_min      5.243
_cell_measurement_theta_max      54.937

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6837
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
'SADABS. Area-Detector Integration Software. (Siemens Industrial Automation, 1995, Inc.: Madison, WI)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8224
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         27.51
_reflns_number_total             2417
_reflns_number_gt                2243
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'Bruker SMART. Area-Detector Software Package. (Siemens Industrial Automation, 1993, Inc.: Madison, WI)'
_computing_cell_refinement       
'Bruker SMART. Area-Detector Software Package. (Siemens Industrial Automation, 1993, Inc.: Madison, WI)'
_computing_data_reduction        
'Bruker SAINT. Area-Detector Integration Software. (Siemens Industrial Automation, 1995, Inc.: Madison, WI)'
_computing_structure_solution    
'SHELX-97. Programs for Crystal Structure Analysis. (G. M. Sheldrick, 1997, Release 97-2, University of Gttingen, Germany)'
_computing_structure_refinement  
'SHELX-97. Programs for Crystal Structure Analysis. (G. M. Sheldrick, 1997, Release 97-2, University of Gttingen, Germany)'
_computing_molecular_graphics    
'Ortep for Windows (L. J. Farrugia, J. Appl. Cryst. 1997, 30, 565)'
_computing_publication_material  
'WinGX v1.70.01 (L. J. Farrugia, J. Appl. Cryst. 1999, 32, 837)'

_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)+(0.0349P)²+0.3479P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_number_reflns         2417
_refine_ls_number_parameters     141
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0660
_refine_ls_wR_factor_gt          0.0639
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.424770(18) 0.33030(4) 0.45774(6) 0.01543(10) Uani 1 1 d . . .
F1 F 0.41253(5) 0.39317(12) 0.69584(15) 0.0210(2) Uani 1 1 d . . .
F2 F 0.44053(5) 0.27068(12) 0.22279(15) 0.0225(2) Uani 1 1 d . . .
C1 C 0.24161(10) 0.6001(3) 0.1153(3) 0.0346(5) Uani 1 1 d . . .
H1 H 0.2043 0.6587 0.0469 0.042 Uiso 1 1 calc R . .
C2 C 0.24518(9) 0.5370(2) 0.3177(4) 0.0335(5) Uani 1 1 d . . .
H5 H 0.2101 0.5512 0.3876 0.040 Uiso 1 1 calc R . .
C3 C 0.29970(8) 0.4529(2) 0.4199(3) 0.0238(4) Uani 1 1 d . . .
H6 H 0.3018 0.4100 0.5595 0.029 Uiso 1 1 calc R . .
C4 C 0.35167(7) 0.43107(19) 0.3178(3) 0.0171(3) Uani 1 1 d . . .
C5 C 0.5000 0.4462(3) 0.5000 0.0239(5) Uani 1 2 d S . .
H11 H 0.5018 0.5161 0.6267 0.029 Uiso 0.50 1 calc PR . .
H12 H 0.4982 0.5161 0.3733 0.029 Uiso 0.50 1 calc PR . .
C6 C 0.41831(7) 0.12423(19) 0.5398(3) 0.0169(3) Uani 1 1 d . . .
C7 C 0.43155(8) 0.0799(2) 0.7557(3) 0.0195(3) Uani 1 1 d . . .
H8 H 0.4450 0.1581 0.8642 0.023 Uiso 1 1 calc R . .
C8 C 0.42512(8) -0.0779(2) 0.8134(3) 0.0242(4) Uani 1 1 d . . .
H9 H 0.4354 -0.1076 0.9610 0.029 Uiso 1 1 calc R . .
C9 C 0.40390(9) -0.1923(2) 0.6577(3) 0.0301(4) Uani 1 1 d . . .
H2 H 0.3991 -0.3000 0.6979 0.036 Uiso 1 1 calc R . .
C10 C 0.38967(10) -0.1487(2) 0.4426(3) 0.0335(4) Uani 1 1 d . . .
H7 H 0.3746 -0.2266 0.3350 0.040 Uiso 1 1 calc R . .
C11 C 0.39729(9) 0.0077(2) 0.3833(3) 0.0249(4) Uani 1 1 d . . .
H10 H 0.3882 0.0360 0.2351 0.030 Uiso 1 1 calc R . .
C12 C 0.29232(10) 0.5781(2) 0.0115(3) 0.0322(5) Uani 1 1 d . . .
H4 H 0.2898 0.6217 -0.1280 0.039 Uiso 1 1 calc R . .
C13 C 0.34684(9) 0.4926(2) 0.1104(3) 0.0241(4) Uani 1 1 d . . .
H3 H 0.3810 0.4758 0.0370 0.029 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 F1 1.6743(11) . ?
P1 F2 1.6746(11) . ?
P1 C4 1.8154(16) . ?
P1 C6 1.8190(17) . ?
P1 C5 1.8314(14) . ?
C1 C2 1.378(3) . ?
C1 C12 1.384(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(3) . ?
C2 H5 0.9500 . ?
C3 C4 1.401(2) . ?
C3 H6 0.9500 . ?
C4 C13 1.399(2) . ?
C5 P1 1.8314(14) 2_656 ?
C5 H11 0.9900 . ?
C5 H12 0.9900 . ?
C6 C7 1.392(2) . ?
C6 C11 1.398(2) . ?
C7 C8 1.388(3) . ?
C7 H8 0.9500 . ?
C8 C9 1.382(3) . ?
C8 H9 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H2 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H7 0.9500 . ?
C11 H10 0.9500 . ?
C12 C13 1.386(3) . ?
C12 H4 0.9500 . ?
C13 H3 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 P1 F2 177.35(6) . . ?
F1 P1 C4 90.96(6) . . ?
F2 P1 C4 90.71(6) . . ?
F1 P1 C6 90.27(7) . . ?
F2 P1 C6 90.76(7) . . ?
C4 P1 C6 118.36(7) . . ?
F1 P1 C5 89.83(5) . . ?
F2 P1 C5 87.58(5) . . ?
C4 P1 C5 116.30(8) . . ?
C6 P1 C5 125.34(8) . . ?
C2 C1 C12 120.02(18) . . ?
C2 C1 H1 120.0 . . ?
C12 C1 H1 120.0 . . ?
C1 C2 C3 120.43(19) . . ?
C1 C2 H5 119.8 . . ?
C3 C2 H5 119.8 . . ?
C2 C3 C4 120.18(18) . . ?
C2 C3 H6 119.9 . . ?
C4 C3 H6 119.9 . . ?
C13 C4 C3 118.82(15) . . ?
C13 C4 P1 121.08(13) . . ?
C3 C4 P1 120.07(13) . . ?
P1 C5 P1 115.85(14) . 2_656 ?
P1 C5 H11 108.3 . . ?
P1 C5 H11 108.3 2_656 . ?
P1 C5 H12 108.3 . . ?
P1 C5 H12 108.3 2_656 . ?
H11 C5 H12 107.4 . . ?
C7 C6 C11 118.77(17) . . ?
C7 C6 P1 121.67(12) . . ?
C11 C6 P1 119.52(14) . . ?
C8 C7 C6 120.33(16) . . ?
C8 C7 H8 119.8 . . ?
C6 C7 H8 119.8 . . ?
C9 C8 C7 120.53(17) . . ?
C9 C8 H9 119.7 . . ?
C7 C8 H9 119.7 . . ?
C8 C9 C10 119.47(18) . . ?
C8 C9 H2 120.3 . . ?
C10 C9 H2 120.3 . . ?
C11 C10 C9 120.42(18) . . ?
C11 C10 H7 119.8 . . ?
C9 C10 H7 119.8 . . ?
C10 C11 C6 120.46(18) . . ?
C10 C11 H10 119.8 . . ?
C6 C11 H10 119.8 . . ?
C1 C12 C13 120.26(19) . . ?
C1 C12 H4 119.9 . . ?
C13 C12 H4 119.9 . . ?
C12 C13 C4 120.25(18) . . ?
C12 C13 H3 119.9 . . ?
C4 C13 H3 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C1 C2 C3 0.8(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C13 -1.3(3) . . . . ?
C2 C3 C4 P1 176.66(14) . . . . ?
F1 P1 C4 C13 148.83(14) . . . . ?
F2 P1 C4 C13 -29.11(14) . . . . ?
C6 P1 C4 C13 -120.35(14) . . . . ?
C5 P1 C4 C13 58.54(15) . . . . ?
F1 P1 C4 C3 -29.09(14) . . . . ?
F2 P1 C4 C3 152.98(14) . . . . ?
C6 P1 C4 C3 61.74(16) . . . . ?
C5 P1 C4 C3 -119.37(13) . . . . ?
F1 P1 C5 P1 111.70(4) . . . 2_656 ?
F2 P1 C5 P1 -67.71(4) . . . 2_656 ?
C4 P1 C5 P1 -157.31(6) . . . 2_656 ?
C6 P1 C5 P1 21.50(7) . . . 2_656 ?
F1 P1 C6 C7 -24.74(14) . . . . ?
F2 P1 C6 C7 152.82(13) . . . . ?
C4 P1 C6 C7 -115.97(14) . . . . ?
C5 P1 C6 C7 65.24(15) . . . . ?
F1 P1 C6 C11 152.89(14) . . . . ?
F2 P1 C6 C11 -29.56(14) . . . . ?
C4 P1 C6 C11 61.65(16) . . . . ?
C5 P1 C6 C11 -117.13(13) . . . . ?
C11 C6 C7 C8 1.3(2) . . . . ?
P1 C6 C7 C8 178.90(13) . . . . ?
C6 C7 C8 C9 -1.7(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C10 C11 C6 -1.2(3) . . . . ?
C7 C6 C11 C10 0.2(3) . . . . ?
P1 C6 C11 C10 -177.53(15) . . . . ?
C2 C1 C12 C13 0.0(3) . . . . ?
C1 C12 C13 C4 -1.5(3) . . . . ?
C3 C4 C13 C12 2.1(3) . . . . ?
P1 C4 C13 C12 -175.86(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_3_[(C10H6)(Ph2P)(Ph2PF)][B(C6F5)4]
_audit_block_doi                 10.5517/cc13ytql
_database_code_depnum_ccdc_archive 'CCDC 1041560'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5SC00051C 2015
_audit_update_record             
;
2014-12-30 deposited with the CCDC.
2015-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 B F20, C34 H26 F P2'
_chemical_formula_sum            'C58 H26 B F21 P2'
_chemical_formula_weight         1194.54

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   8.4256(12)
_cell_length_b                   21.123(3)
_cell_length_c                   13.804(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.055(7)
_cell_angle_gamma                90.00
_cell_volume                     2447.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      4.853
_cell_measurement_theta_max      48.604

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1196
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6987
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
'SADABS. Area-Detector Integration Software. (Siemens Industrial Automation, 1995, Inc.: Madison, WI)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            41120
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.1006
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         27.46
_reflns_number_total             10858
_reflns_number_gt                7111
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'Bruker SMART. Area-Detector Software Package. (Siemens Industrial Automation, 1993, Inc.: Madison, WI)'
_computing_cell_refinement       
'Bruker SMART. Area-Detector Software Package. (Siemens Industrial Automation, 1993, Inc.: Madison, WI)'
_computing_data_reduction        
'Bruker SAINT. Area-Detector Integration Software. (Siemens Industrial Automation, 1995, Inc.: Madison, WI)'
_computing_structure_solution    
'SHELX-97. Programs for Crystal Structure Analysis. (G. M. Sheldrick, 1997, Release 97-2, University of Gttingen, Germany)'
_computing_structure_refinement  
'SHELX-97. Programs for Crystal Structure Analysis. (G. M. Sheldrick, 1997, Release 97-2, University of Gttingen, Germany)'
_computing_molecular_graphics    
'Ortep for Windows (L. J. Farrugia, J. Appl. Cryst. 1997, 30, 565)'
_computing_publication_material  
'WinGX v1.70.01 (L. J. Farrugia, J. Appl. Cryst. 1999, 32, 837)'

_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)+(0.0309P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_number_reflns         10858
_refine_ls_number_parameters     739
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.0852
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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 0.43371(10) 0.48157(4) 0.52415(6) 0.01911(19) Uani 1 1 d . . .
P2 P 0.16059(11) 0.51177(4) 0.44719(6) 0.0230(2) Uani 1 1 d . . .
F1 F -0.0147(2) 0.53106(8) 0.39493(13) 0.0318(5) Uani 1 1 d . . .
F2 F 1.3829(3) 0.29981(10) 1.35596(16) 0.0531(7) Uani 1 1 d . . .
F3 F 0.5241(3) 0.02653(10) 1.02240(17) 0.0574(7) Uani 1 1 d . . .
F4 F 1.2867(2) 0.06976(9) 0.71507(14) 0.0376(5) Uani 1 1 d . . .
F5 F 1.2440(2) 0.02586(9) 0.89643(14) 0.0394(5) Uani 1 1 d . . .
F6 F 1.1378(2) 0.10354(8) 1.02991(13) 0.0311(5) Uani 1 1 d . . .
F7 F 1.0511(2) 0.26224(8) 0.78739(13) 0.0318(5) Uani 1 1 d . . .
F8 F 1.1860(2) 0.18938(9) 0.66325(13) 0.0402(6) Uani 1 1 d . . .
F9 F 0.9242(2) 0.14891(9) 1.18417(13) 0.0323(5) Uani 1 1 d . . .
F10 F 0.7089(3) 0.05852(9) 1.18630(15) 0.0456(6) Uani 1 1 d . . .
F11 F 0.5537(2) 0.09254(10) 0.85258(16) 0.0453(6) Uani 1 1 d . . .
F12 F 0.7555(2) 0.18862(8) 0.85110(13) 0.0307(5) Uani 1 1 d . . .
F13 F 1.1936(2) 0.32881(8) 0.94715(14) 0.0328(5) Uani 1 1 d . . .
F14 F 1.1078(3) 0.44765(9) 0.90028(15) 0.0451(6) Uani 1 1 d . . .
F15 F 0.7956(3) 0.48347(9) 0.89665(15) 0.0501(6) Uani 1 1 d . . .
F16 F 0.5762(3) 0.39882(9) 0.95212(15) 0.0456(6) Uani 1 1 d . . .
F17 F 0.6556(2) 0.28081(8) 0.99189(15) 0.0364(5) Uani 1 1 d . . .
F18 F 0.8886(2) 0.28069(8) 1.17505(14) 0.0340(5) Uani 1 1 d . . .
F19 F 1.0603(3) 0.31583(10) 1.33618(15) 0.0546(7) Uani 1 1 d . . .
F20 F 1.5285(3) 0.24651(11) 1.20600(16) 0.0513(6) Uani 1 1 d . . .
F21 F 1.3607(2) 0.20944(10) 1.04457(15) 0.0385(5) Uani 1 1 d . . .
C1 C 0.7823(4) 0.63542(15) 0.6472(3) 0.0300(9) Uani 1 1 d . . .
H1 H 0.8566 0.6667 0.6711 0.036 Uiso 1 1 calc R . .
C2 C 0.7212(4) 0.59305(15) 0.7104(2) 0.0266(8) Uani 1 1 d . . .
H7 H 0.7515 0.5960 0.7782 0.032 Uiso 1 1 calc R . .
C3 C 0.6158(4) 0.54619(15) 0.6753(2) 0.0217(8) Uani 1 1 d . . .
H8 H 0.5747 0.5170 0.7191 0.026 Uiso 1 1 calc R . .
C4 C 0.5701(4) 0.54183(13) 0.5756(2) 0.0199(7) Uani 1 1 d . . .
C5 C 0.2032(4) 0.59263(15) 0.4818(2) 0.0252(8) Uani 1 1 d . . .
C6 C 0.2326(4) 0.61119(16) 0.5789(3) 0.0284(9) Uani 1 1 d . . .
H9 H 0.2410 0.5803 0.6290 0.034 Uiso 1 1 calc R . .
C7 C 0.2495(4) 0.67465(17) 0.6018(3) 0.0410(10) Uani 1 1 d . . .
H10 H 0.2666 0.6874 0.6679 0.049 Uiso 1 1 calc R . .
C8 C 0.2416(5) 0.71980(18) 0.5284(4) 0.0485(12) Uani 1 1 d . . .
H2 H 0.2555 0.7633 0.5442 0.058 Uiso 1 1 calc R . .
C9 C 0.4259(5) 0.31501(18) 0.7383(3) 0.0412(10) Uani 1 1 d . . .
H3 H 0.4231 0.2809 0.7829 0.049 Uiso 1 1 calc R . .
C10 C 0.3724(4) 0.37447(17) 0.7627(3) 0.0330(9) Uani 1 1 d . . .
H26 H 0.3325 0.3811 0.8241 0.040 Uiso 1 1 calc R . .
C11 C 0.3769(4) 0.42404(16) 0.6977(2) 0.0248(8) Uani 1 1 d . . .
H4 H 0.3366 0.4643 0.7138 0.030 Uiso 1 1 calc R . .
C12 C 0.4405(4) 0.41540(14) 0.6080(2) 0.0203(7) Uani 1 1 d . . .
C13 C 0.7348(4) 0.63213(16) 0.5488(3) 0.0339(9) Uani 1 1 d . . .
H6 H 0.7753 0.6619 0.5057 0.041 Uiso 1 1 calc R . .
C14 C 0.6292(4) 0.58598(15) 0.5123(3) 0.0278(8) Uani 1 1 d . . .
H5 H 0.5971 0.5843 0.4447 0.033 Uiso 1 1 calc R . .
C15 C 0.5069(4) 0.45546(14) 0.4130(2) 0.0205(8) Uani 1 1 d . . .
C16 C 0.6586(4) 0.43369(15) 0.4042(2) 0.0276(8) Uani 1 1 d . . .
H23 H 0.7347 0.4341 0.4592 0.033 Uiso 1 1 calc R . .
C17 C 0.7028(5) 0.41094(15) 0.3148(3) 0.0319(9) Uani 1 1 d . . .
H22 H 0.8073 0.3951 0.3097 0.038 Uiso 1 1 calc R . .
C18 C 0.5939(5) 0.41173(16) 0.2351(3) 0.0347(10) Uani 1 1 d . . .
H21 H 0.6250 0.3963 0.1749 0.042 Uiso 1 1 calc R . .
C19 C 0.4374(4) 0.43452(15) 0.2390(2) 0.0286(9) Uani 1 1 d . . .
C20 C 0.3255(5) 0.43495(17) 0.1568(3) 0.0376(10) Uani 1 1 d . . .
H20 H 0.3560 0.4202 0.0962 0.045 Uiso 1 1 calc R . .
C21 C 0.1746(5) 0.45623(19) 0.1632(3) 0.0472(11) Uani 1 1 d . . .
H19 H 0.1003 0.4556 0.1073 0.057 Uiso 1 1 calc R . .
C22 C 0.1276(5) 0.47926(17) 0.2522(2) 0.0366(9) Uani 1 1 d . . .
H18 H 0.0222 0.4947 0.2550 0.044 Uiso 1 1 calc R . .
C23 C 0.2323(4) 0.47982(15) 0.3357(2) 0.0235(8) Uani 1 1 d . . .
C24 C 0.1937(4) 0.63829(17) 0.4083(3) 0.0348(9) Uani 1 1 d . . .
H12 H 0.1737 0.6260 0.3422 0.042 Uiso 1 1 calc R . .
C25 C 0.2136(5) 0.70149(18) 0.4324(4) 0.0463(11) Uani 1 1 d . . .
H11 H 0.2079 0.7326 0.3825 0.056 Uiso 1 1 calc R . .
C26 C 0.0777(4) 0.45809(15) 0.5308(2) 0.0206(7) Uani 1 1 d . . .
C27 C -0.0140(4) 0.48140(16) 0.6021(2) 0.0257(8) Uani 1 1 d . . .
H17 H -0.0305 0.5257 0.6082 0.031 Uiso 1 1 calc R . .
C28 C -0.0810(4) 0.43930(17) 0.6644(3) 0.0304(9) Uani 1 1 d . . .
H16 H -0.1410 0.4549 0.7144 0.036 Uiso 1 1 calc R . .
C29 C -0.0607(4) 0.37464(17) 0.6538(3) 0.0302(9) Uani 1 1 d . . .
H15 H -0.1078 0.3460 0.6960 0.036 Uiso 1 1 calc R . .
C30 C 0.0280(4) 0.35175(16) 0.5820(3) 0.0320(9) Uani 1 1 d . . .
H13 H 0.0409 0.3074 0.5746 0.038 Uiso 1 1 calc R . .
C31 C 0.0980(4) 0.39304(15) 0.5210(2) 0.0254(8) Uani 1 1 d . . .
H14 H 0.1601 0.3771 0.4722 0.031 Uiso 1 1 calc R . .
C32 C 0.3918(4) 0.45716(15) 0.3308(2) 0.0240(8) Uani 1 1 d . . .
C33 C 0.4920(4) 0.35523(15) 0.5840(3) 0.0300(9) Uani 1 1 d . . .
H25 H 0.5332 0.3483 0.5230 0.036 Uiso 1 1 calc R . .
C34 C 0.4834(4) 0.30571(17) 0.6485(3) 0.0406(10) Uani 1 1 d . . .
H24 H 0.5174 0.2647 0.6310 0.049 Uiso 1 1 calc R . .
C35 C 1.2971(5) 0.28210(16) 1.2730(3) 0.0365(10) Uani 1 1 d . . .
C36 C 1.1339(5) 0.29029(15) 1.2625(3) 0.0338(9) Uani 1 1 d . . .
C37 C 1.0482(4) 0.27048(15) 1.1785(2) 0.0253(8) Uani 1 1 d . . .
C38 C 1.1128(4) 0.24153(14) 1.1002(2) 0.0215(8) Uani 1 1 d . . .
C39 C 0.8520(4) 0.17556(14) 1.0173(2) 0.0192(7) Uani 1 1 d . . .
C40 C 0.7491(4) 0.15754(15) 0.9374(2) 0.0233(8) Uani 1 1 d . . .
C41 C 0.6421(4) 0.10844(16) 0.9359(3) 0.0275(8) Uani 1 1 d . . .
C42 C 0.6272(4) 0.07463(16) 1.0205(3) 0.0361(10) Uani 1 1 d . . .
C43 C 1.2199(4) 0.10724(17) 0.7797(2) 0.0278(8) Uani 1 1 d . . .
C44 C 1.2022(4) 0.08609(16) 0.8724(3) 0.0269(8) Uani 1 1 d . . .
C45 C 1.1432(4) 0.12679(15) 0.9385(2) 0.0223(8) Uani 1 1 d . . .
C46 C 1.0900(4) 0.18802(14) 0.9179(2) 0.0200(7) Uani 1 1 d . . .
C47 C 1.1054(4) 0.20530(15) 0.8223(2) 0.0233(8) Uani 1 1 d . . .
C48 C 1.1720(4) 0.16740(16) 0.7543(2) 0.0240(8) Uani 1 1 d . . .
C49 C 0.8307(4) 0.13974(15) 1.1000(2) 0.0248(8) Uani 1 1 d . . .
C50 C 0.7210(4) 0.09143(16) 1.1022(3) 0.0305(9) Uani 1 1 d . . .
C51 C 0.9298(4) 0.29686(14) 0.9670(2) 0.0215(8) Uani 1 1 d . . .
C52 C 1.0356(4) 0.34330(15) 0.9453(2) 0.0255(8) Uani 1 1 d . . .
C53 C 0.9952(5) 0.40525(15) 0.9215(2) 0.0306(9) Uani 1 1 d . . .
C54 C 0.8388(5) 0.42361(15) 0.9215(2) 0.0301(9) Uani 1 1 d . . .
C55 C 0.7279(5) 0.38073(16) 0.9467(3) 0.0300(9) Uani 1 1 d . . .
C56 C 0.7740(4) 0.31900(15) 0.9678(2) 0.0260(8) Uani 1 1 d . . .
C57 C 1.3684(5) 0.25439(17) 1.1982(3) 0.0330(9) Uani 1 1 d . . .
C58 C 1.2771(4) 0.23537(15) 1.1145(2) 0.0263(8) Uani 1 1 d . . .
B1 B 0.9963(5) 0.22559(17) 1.0010(3) 0.0212(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 C15 1.790(3) . ?
P1 C12 1.812(3) . ?
P1 C4 1.817(3) . ?
P1 P2 2.5299(13) . ?
P2 F1 1.637(2) . ?
P2 C5 1.801(3) . ?
P2 C26 1.802(3) . ?
P2 C23 1.831(3) . ?
F2 C35 1.352(4) . ?
F3 C42 1.338(4) . ?
F4 C43 1.352(4) . ?
F5 C44 1.353(4) . ?
F6 C45 1.359(4) . ?
F7 C47 1.360(4) . ?
F8 C48 1.355(4) . ?
F9 C49 1.359(4) . ?
F10 C50 1.364(4) . ?
F11 C41 1.356(4) . ?
F12 C40 1.365(4) . ?
F13 C52 1.364(4) . ?
F14 C53 1.355(4) . ?
F15 C54 1.352(4) . ?
F16 C55 1.343(4) . ?
F17 C56 1.347(4) . ?
F18 C37 1.358(4) . ?
F19 C36 1.349(4) . ?
F20 C57 1.354(4) . ?
F21 C58 1.359(4) . ?
C1 C2 1.381(5) . ?
C1 C13 1.383(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(4) . ?
C2 H7 0.9500 . ?
C3 C4 1.399(4) . ?
C3 H8 0.9500 . ?
C4 C14 1.399(4) . ?
C5 C6 1.397(5) . ?
C5 C24 1.397(5) . ?
C6 C7 1.382(5) . ?
C6 H9 0.9500 . ?
C7 C8 1.389(6) . ?
C7 H10 0.9500 . ?
C8 C25 1.380(6) . ?
C8 H2 0.9500 . ?
C9 C34 1.384(5) . ?
C9 C10 1.386(5) . ?
C9 H3 0.9500 . ?
C10 C11 1.382(5) . ?
C10 H26 0.9500 . ?
C11 C12 1.403(4) . ?
C11 H4 0.9500 . ?
C12 C33 1.393(4) . ?
C13 C14 1.385(5) . ?
C13 H6 0.9500 . ?
C14 H5 0.9500 . ?
C15 C16 1.375(4) . ?
C15 C32 1.427(4) . ?
C16 C17 1.404(4) . ?
C16 H23 0.9500 . ?
C17 C18 1.370(5) . ?
C17 H22 0.9500 . ?
C18 C19 1.409(5) . ?
C18 H21 0.9500 . ?
C19 C20 1.409(5) . ?
C19 C32 1.439(4) . ?
C20 C21 1.358(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.409(5) . ?
C21 H19 0.9500 . ?
C22 C23 1.389(4) . ?
C22 H18 0.9500 . ?
C23 C32 1.434(5) . ?
C24 C25 1.382(5) . ?
C24 H12 0.9500 . ?
C25 H11 0.9500 . ?
C26 C31 1.393(4) . ?
C26 C27 1.394(4) . ?
C27 C28 1.391(4) . ?
C27 H17 0.9500 . ?
C28 C29 1.386(5) . ?
C28 H16 0.9500 . ?
C29 C30 1.380(5) . ?
C29 H15 0.9500 . ?
C30 C31 1.381(4) . ?
C30 H13 0.9500 . ?
C31 H14 0.9500 . ?
C33 C34 1.380(5) . ?
C33 H25 0.9500 . ?
C34 H24 0.9500 . ?
C35 C57 1.371(5) . ?
C35 C36 1.381(5) . ?
C36 C37 1.377(5) . ?
C37 C38 1.394(4) . ?
C38 C58 1.387(5) . ?
C38 B1 1.647(5) . ?
C39 C49 1.395(4) . ?
C39 C40 1.395(4) . ?
C39 B1 1.642(5) . ?
C40 C41 1.374(4) . ?
C41 C42 1.384(5) . ?
C42 C50 1.366(5) . ?
C43 C48 1.369(5) . ?
C43 C44 1.377(5) . ?
C44 C45 1.378(4) . ?
C45 C46 1.390(4) . ?
C46 C47 1.386(4) . ?
C46 B1 1.652(5) . ?
C47 C48 1.389(4) . ?
C49 C50 1.379(5) . ?
C51 C52 1.376(4) . ?
C51 C56 1.394(4) . ?
C51 B1 1.660(5) . ?
C52 C53 1.385(5) . ?
C53 C54 1.374(5) . ?
C54 C55 1.367(5) . ?
C55 C56 1.384(4) . ?
C57 C58 1.389(5) . ?

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
C15 P1 C12 108.41(14) . . ?
C15 P1 C4 107.29(15) . . ?
C12 P1 C4 107.91(15) . . ?
C15 P1 P2 94.99(12) . . ?
C12 P1 P2 116.03(11) . . ?
C4 P1 P2 120.53(10) . . ?
F1 P2 C5 91.84(13) . . ?
F1 P2 C26 93.06(13) . . ?
C5 P2 C26 120.41(15) . . ?
F1 P2 C23 94.19(13) . . ?
C5 P2 C23 119.99(15) . . ?
C26 P2 C23 118.77(15) . . ?
F1 P2 P1 178.68(8) . . ?
C5 P2 P1 88.56(11) . . ?
C26 P2 P1 87.82(11) . . ?
C23 P2 P1 84.53(11) . . ?
C2 C1 C13 119.8(3) . . ?
C2 C1 H1 120.1 . . ?
C13 C1 H1 120.1 . . ?
C1 C2 C3 120.3(3) . . ?
C1 C2 H7 119.9 . . ?
C3 C2 H7 119.9 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H8 119.9 . . ?
C4 C3 H8 119.9 . . ?
C14 C4 C3 119.2(3) . . ?
C14 C4 P1 118.1(3) . . ?
C3 C4 P1 122.7(2) . . ?
C6 C5 C24 119.8(3) . . ?
C6 C5 P2 122.3(3) . . ?
C24 C5 P2 117.7(3) . . ?
C7 C6 C5 119.9(3) . . ?
C7 C6 H9 120.1 . . ?
C5 C6 H9 120.1 . . ?
C6 C7 C8 120.1(4) . . ?
C6 C7 H10 120.0 . . ?
C8 C7 H10 120.0 . . ?
C25 C8 C7 120.1(4) . . ?
C25 C8 H2 120.0 . . ?
C7 C8 H2 120.0 . . ?
C34 C9 C10 119.5(3) . . ?
C34 C9 H3 120.2 . . ?
C10 C9 H3 120.2 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H26 120.0 . . ?
C9 C10 H26 120.0 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H4 119.7 . . ?
C12 C11 H4 119.7 . . ?
C33 C12 C11 118.7(3) . . ?
C33 C12 P1 123.0(3) . . ?
C11 C12 P1 118.0(2) . . ?
C1 C13 C14 120.9(3) . . ?
C1 C13 H6 119.6 . . ?
C14 C13 H6 119.6 . . ?
C13 C14 C4 119.7(3) . . ?
C13 C14 H5 120.2 . . ?
C4 C14 H5 120.2 . . ?
C16 C15 C32 120.7(3) . . ?
C16 C15 P1 125.0(3) . . ?
C32 C15 P1 114.4(2) . . ?
C15 C16 C17 120.9(3) . . ?
C15 C16 H23 119.5 . . ?
C17 C16 H23 119.5 . . ?
C18 C17 C16 119.4(3) . . ?
C18 C17 H22 120.3 . . ?
C16 C17 H22 120.3 . . ?
C17 C18 C19 122.4(3) . . ?
C17 C18 H21 118.8 . . ?
C19 C18 H21 118.8 . . ?
C18 C19 C20 122.2(3) . . ?
C18 C19 C32 118.1(3) . . ?
C20 C19 C32 119.7(3) . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 120.5(4) . . ?
C20 C21 H19 119.8 . . ?
C22 C21 H19 119.8 . . ?
C23 C22 C21 121.3(4) . . ?
C23 C22 H18 119.3 . . ?
C21 C22 H18 119.3 . . ?
C22 C23 C32 119.1(3) . . ?
C22 C23 P2 118.0(3) . . ?
C32 C23 P2 122.9(2) . . ?
C25 C24 C5 119.6(4) . . ?
C25 C24 H12 120.2 . . ?
C5 C24 H12 120.2 . . ?
C8 C25 C24 120.6(4) . . ?
C8 C25 H11 119.7 . . ?
C24 C25 H11 119.7 . . ?
C31 C26 C27 119.8(3) . . ?
C31 C26 P2 120.1(3) . . ?
C27 C26 P2 120.0(2) . . ?
C28 C27 C26 119.4(3) . . ?
C28 C27 H17 120.3 . . ?
C26 C27 H17 120.3 . . ?
C29 C28 C27 120.3(3) . . ?
C29 C28 H16 119.9 . . ?
C27 C28 H16 119.9 . . ?
C30 C29 C28 120.1(3) . . ?
C30 C29 H15 120.0 . . ?
C28 C29 H15 120.0 . . ?
C29 C30 C31 120.3(3) . . ?
C29 C30 H13 119.9 . . ?
C31 C30 H13 119.9 . . ?
C30 C31 C26 120.1(3) . . ?
C30 C31 H14 120.0 . . ?
C26 C31 H14 120.0 . . ?
C15 C32 C23 123.0(3) . . ?
C15 C32 C19 118.5(3) . . ?
C23 C32 C19 118.5(3) . . ?
C34 C33 C12 120.2(3) . . ?
C34 C33 H25 119.9 . . ?
C12 C33 H25 119.9 . . ?
C33 C34 C9 120.9(3) . . ?
C33 C34 H24 119.6 . . ?
C9 C34 H24 119.6 . . ?
F2 C35 C57 121.3(4) . . ?
F2 C35 C36 120.5(4) . . ?
C57 C35 C36 118.2(3) . . ?
F19 C36 C37 121.0(4) . . ?
F19 C36 C35 119.4(3) . . ?
C37 C36 C35 119.6(3) . . ?
F18 C37 C36 115.1(3) . . ?
F18 C37 C38 119.7(3) . . ?
C36 C37 C38 125.1(3) . . ?
C58 C38 C37 112.5(3) . . ?
C58 C38 B1 127.9(3) . . ?
C37 C38 B1 119.3(3) . . ?
C49 C39 C40 112.6(3) . . ?
C49 C39 B1 127.7(3) . . ?
C40 C39 B1 118.9(3) . . ?
F12 C40 C41 115.3(3) . . ?
F12 C40 C39 119.3(3) . . ?
C41 C40 C39 125.4(3) . . ?
F11 C41 C40 120.7(3) . . ?
F11 C41 C42 120.3(3) . . ?
C40 C41 C42 119.1(3) . . ?
F3 C42 C50 120.7(3) . . ?
F3 C42 C41 121.0(3) . . ?
C50 C42 C41 118.3(3) . . ?
F4 C43 C48 120.4(3) . . ?
F4 C43 C44 120.6(3) . . ?
C48 C43 C44 119.0(3) . . ?
F5 C44 C43 119.1(3) . . ?
F5 C44 C45 121.7(3) . . ?
C43 C44 C45 119.2(3) . . ?
F6 C45 C44 115.6(3) . . ?
F6 C45 C46 119.3(3) . . ?
C44 C45 C46 125.1(3) . . ?
C47 C46 C45 112.6(3) . . ?
C47 C46 B1 128.7(3) . . ?
C45 C46 B1 118.0(3) . . ?
F7 C47 C46 120.9(3) . . ?
F7 C47 C48 114.4(3) . . ?
C46 C47 C48 124.6(3) . . ?
F8 C48 C43 120.5(3) . . ?
F8 C48 C47 120.2(3) . . ?
C43 C48 C47 119.3(3) . . ?
F9 C49 C50 115.2(3) . . ?
F9 C49 C39 121.0(3) . . ?
C50 C49 C39 123.7(3) . . ?
F10 C50 C42 119.3(3) . . ?
F10 C50 C49 119.8(3) . . ?
C42 C50 C49 120.9(3) . . ?
C52 C51 C56 113.0(3) . . ?
C52 C51 B1 119.9(3) . . ?
C56 C51 B1 126.6(3) . . ?
F13 C52 C51 119.1(3) . . ?
F13 C52 C53 115.8(3) . . ?
C51 C52 C53 125.1(3) . . ?
F14 C53 C54 120.2(3) . . ?
F14 C53 C52 120.9(4) . . ?
C54 C53 C52 118.8(3) . . ?
F15 C54 C55 120.6(3) . . ?
F15 C54 C53 120.0(3) . . ?
C55 C54 C53 119.3(3) . . ?
F16 C55 C54 120.0(3) . . ?
F16 C55 C56 120.5(3) . . ?
C54 C55 C56 119.5(3) . . ?
F17 C56 C55 114.6(3) . . ?
F17 C56 C51 121.3(3) . . ?
C55 C56 C51 124.1(3) . . ?
F20 C57 C35 119.5(3) . . ?
F20 C57 C58 120.4(4) . . ?
C35 C57 C58 120.1(4) . . ?
F21 C58 C38 120.6(3) . . ?
F21 C58 C57 115.0(3) . . ?
C38 C58 C57 124.4(3) . . ?
C39 B1 C38 114.3(3) . . ?
C39 B1 C46 101.0(2) . . ?
C38 B1 C46 112.9(3) . . ?
C39 B1 C51 112.7(3) . . ?
C38 B1 C51 102.2(3) . . ?
C46 B1 C51 114.2(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
C15 P1 P2 F1 -9(4) . . . . ?
C12 P1 P2 F1 -122(4) . . . . ?
C4 P1 P2 F1 104(4) . . . . ?
C15 P1 P2 C5 -116.62(15) . . . . ?
C12 P1 P2 C5 130.09(16) . . . . ?
C4 P1 P2 C5 -3.17(17) . . . . ?
C15 P1 P2 C26 122.87(14) . . . . ?
C12 P1 P2 C26 9.58(15) . . . . ?
C4 P1 P2 C26 -123.68(16) . . . . ?
C15 P1 P2 C23 3.70(14) . . . . ?
C12 P1 P2 C23 -109.60(15) . . . . ?
C4 P1 P2 C23 117.14(16) . . . . ?
C13 C1 C2 C3 1.7(5) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C14 -1.3(5) . . . . ?
C2 C3 C4 P1 179.6(2) . . . . ?
C15 P1 C4 C14 40.8(3) . . . . ?
C12 P1 C4 C14 157.4(2) . . . . ?
P2 P1 C4 C14 -66.0(3) . . . . ?
C15 P1 C4 C3 -140.2(3) . . . . ?
C12 P1 C4 C3 -23.5(3) . . . . ?
P2 P1 C4 C3 113.0(3) . . . . ?
F1 P2 C5 C6 119.2(3) . . . . ?
C26 P2 C5 C6 24.6(4) . . . . ?
C23 P2 C5 C6 -144.9(3) . . . . ?
P1 P2 C5 C6 -62.0(3) . . . . ?
F1 P2 C5 C24 -55.7(3) . . . . ?
C26 P2 C5 C24 -150.3(3) . . . . ?
C23 P2 C5 C24 40.2(3) . . . . ?
P1 P2 C5 C24 123.0(3) . . . . ?
C24 C5 C6 C7 1.1(5) . . . . ?
P2 C5 C6 C7 -173.8(3) . . . . ?
C5 C6 C7 C8 -1.7(5) . . . . ?
C6 C7 C8 C25 1.3(6) . . . . ?
C34 C9 C10 C11 -0.2(6) . . . . ?
C9 C10 C11 C12 -2.2(5) . . . . ?
C10 C11 C12 C33 2.9(5) . . . . ?
C10 C11 C12 P1 177.1(3) . . . . ?
C15 P1 C12 C33 -1.3(3) . . . . ?
C4 P1 C12 C33 -117.2(3) . . . . ?
P2 P1 C12 C33 104.0(3) . . . . ?
C15 P1 C12 C11 -175.3(3) . . . . ?
C4 P1 C12 C11 68.8(3) . . . . ?
P2 P1 C12 C11 -69.9(3) . . . . ?
C2 C1 C13 C14 -1.4(5) . . . . ?
C1 C13 C14 C4 -0.3(5) . . . . ?
C3 C4 C14 C13 1.6(5) . . . . ?
P1 C4 C14 C13 -179.3(3) . . . . ?
C12 P1 C15 C16 -62.5(3) . . . . ?
C4 P1 C15 C16 53.8(3) . . . . ?
P2 P1 C15 C16 177.9(3) . . . . ?
C12 P1 C15 C32 115.9(2) . . . . ?
C4 P1 C15 C32 -127.8(2) . . . . ?
P2 P1 C15 C32 -3.6(2) . . . . ?
C32 C15 C16 C17 -1.9(5) . . . . ?
P1 C15 C16 C17 176.5(2) . . . . ?
C15 C16 C17 C18 1.4(5) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 C20 -179.7(3) . . . . ?
C17 C18 C19 C32 -0.5(5) . . . . ?
C18 C19 C20 C21 178.9(3) . . . . ?
C32 C19 C20 C21 -0.3(5) . . . . ?
C19 C20 C21 C22 0.9(6) . . . . ?
C20 C21 C22 C23 -1.2(6) . . . . ?
C21 C22 C23 C32 0.7(5) . . . . ?
C21 C22 C23 P2 179.1(3) . . . . ?
F1 P2 C23 C22 -2.3(3) . . . . ?
C5 P2 C23 C22 -96.9(3) . . . . ?
C26 P2 C23 C22 93.5(3) . . . . ?
P1 P2 C23 C22 178.0(3) . . . . ?
F1 P2 C23 C32 176.0(3) . . . . ?
C5 P2 C23 C32 81.4(3) . . . . ?
C26 P2 C23 C32 -88.2(3) . . . . ?
P1 P2 C23 C32 -3.7(3) . . . . ?
C6 C5 C24 C25 0.0(5) . . . . ?
P2 C5 C24 C25 175.1(3) . . . . ?
C7 C8 C25 C24 -0.2(6) . . . . ?
C5 C24 C25 C8 -0.4(6) . . . . ?
F1 P2 C26 C31 109.6(3) . . . . ?
C5 P2 C26 C31 -156.5(3) . . . . ?
C23 P2 C26 C31 13.1(3) . . . . ?
P1 P2 C26 C31 -69.4(3) . . . . ?
F1 P2 C26 C27 -67.0(3) . . . . ?
C5 P2 C26 C27 26.9(3) . . . . ?
C23 P2 C26 C27 -163.5(3) . . . . ?
P1 P2 C26 C27 114.0(3) . . . . ?
C31 C26 C27 C28 1.6(5) . . . . ?
P2 C26 C27 C28 178.2(3) . . . . ?
C26 C27 C28 C29 -1.9(5) . . . . ?
C27 C28 C29 C30 0.8(6) . . . . ?
C28 C29 C30 C31 0.6(6) . . . . ?
C29 C30 C31 C26 -0.8(5) . . . . ?
C27 C26 C31 C30 -0.2(5) . . . . ?
P2 C26 C31 C30 -176.8(3) . . . . ?
C16 C15 C32 C23 -179.5(3) . . . . ?
P1 C15 C32 C23 2.0(4) . . . . ?
C16 C15 C32 C19 1.1(5) . . . . ?
P1 C15 C32 C19 -177.4(2) . . . . ?
C22 C23 C32 C15 -179.4(3) . . . . ?
P2 C23 C32 C15 2.3(4) . . . . ?
C22 C23 C32 C19 -0.1(5) . . . . ?
P2 C23 C32 C19 -178.4(2) . . . . ?
C18 C19 C32 C15 0.0(4) . . . . ?
C20 C19 C32 C15 179.2(3) . . . . ?
C18 C19 C32 C23 -179.3(3) . . . . ?
C20 C19 C32 C23 -0.1(5) . . . . ?
C11 C12 C33 C34 -1.4(5) . . . . ?
P1 C12 C33 C34 -175.3(3) . . . . ?
C12 C33 C34 C9 -0.9(6) . . . . ?
C10 C9 C34 C33 1.7(6) . . . . ?
F2 C35 C36 F19 -0.4(5) . . . . ?
C57 C35 C36 F19 178.2(3) . . . . ?
F2 C35 C36 C37 -178.4(3) . . . . ?
C57 C35 C36 C37 0.2(5) . . . . ?
F19 C36 C37 F18 2.2(5) . . . . ?
C35 C36 C37 F18 -179.9(3) . . . . ?
F19 C36 C37 C38 -177.6(3) . . . . ?
C35 C36 C37 C38 0.4(5) . . . . ?
F18 C37 C38 C58 179.2(3) . . . . ?
C36 C37 C38 C58 -1.1(5) . . . . ?
F18 C37 C38 B1 5.0(4) . . . . ?
C36 C37 C38 B1 -175.2(3) . . . . ?
C49 C39 C40 F12 179.7(3) . . . . ?
B1 C39 C40 F12 -9.7(4) . . . . ?
C49 C39 C40 C41 -2.8(5) . . . . ?
B1 C39 C40 C41 167.8(3) . . . . ?
F12 C40 C41 F11 1.4(5) . . . . ?
C39 C40 C41 F11 -176.2(3) . . . . ?
F12 C40 C41 C42 -179.6(3) . . . . ?
C39 C40 C41 C42 2.8(5) . . . . ?
F11 C41 C42 F3 -1.1(5) . . . . ?
C40 C41 C42 F3 179.8(3) . . . . ?
F11 C41 C42 C50 178.6(3) . . . . ?
C40 C41 C42 C50 -0.4(5) . . . . ?
F4 C43 C44 F5 -3.9(5) . . . . ?
C48 C43 C44 F5 177.5(3) . . . . ?
F4 C43 C44 C45 175.9(3) . . . . ?
C48 C43 C44 C45 -2.7(5) . . . . ?
F5 C44 C45 F6 3.3(5) . . . . ?
C43 C44 C45 F6 -176.4(3) . . . . ?
F5 C44 C45 C46 -176.4(3) . . . . ?
C43 C44 C45 C46 3.8(5) . . . . ?
F6 C45 C46 C47 179.0(3) . . . . ?
C44 C45 C46 C47 -1.3(5) . . . . ?
F6 C45 C46 B1 -9.5(5) . . . . ?
C44 C45 C46 B1 170.2(3) . . . . ?
C45 C46 C47 F7 176.2(3) . . . . ?
B1 C46 C47 F7 5.9(5) . . . . ?
C45 C46 C47 C48 -2.4(5) . . . . ?
B1 C46 C47 C48 -172.8(3) . . . . ?
F4 C43 C48 F8 2.2(5) . . . . ?
C44 C43 C48 F8 -179.2(3) . . . . ?
F4 C43 C48 C47 -179.2(3) . . . . ?
C44 C43 C48 C47 -0.7(5) . . . . ?
F7 C47 C48 F8 3.3(4) . . . . ?
C46 C47 C48 F8 -178.0(3) . . . . ?
F7 C47 C48 C43 -175.3(3) . . . . ?
C46 C47 C48 C43 3.4(5) . . . . ?
C40 C39 C49 F9 177.6(3) . . . . ?
B1 C39 C49 F9 8.0(5) . . . . ?
C40 C39 C49 C50 0.6(5) . . . . ?
B1 C39 C49 C50 -169.0(3) . . . . ?
F3 C42 C50 F10 0.1(5) . . . . ?
C41 C42 C50 F10 -179.6(3) . . . . ?
F3 C42 C50 C49 178.1(3) . . . . ?
C41 C42 C50 C49 -1.6(5) . . . . ?
F9 C49 C50 F10 2.4(5) . . . . ?
C39 C49 C50 F10 179.6(3) . . . . ?
F9 C49 C50 C42 -175.6(3) . . . . ?
C39 C49 C50 C42 1.6(5) . . . . ?
C56 C51 C52 F13 176.5(3) . . . . ?
B1 C51 C52 F13 3.5(5) . . . . ?
C56 C51 C52 C53 -3.2(5) . . . . ?
B1 C51 C52 C53 -176.2(3) . . . . ?
F13 C52 C53 F14 0.9(5) . . . . ?
C51 C52 C53 F14 -179.4(3) . . . . ?
F13 C52 C53 C54 -177.8(3) . . . . ?
C51 C52 C53 C54 2.0(5) . . . . ?
F14 C53 C54 F15 2.7(5) . . . . ?
C52 C53 C54 F15 -178.7(3) . . . . ?
F14 C53 C54 C55 -177.5(3) . . . . ?
C52 C53 C54 C55 1.1(5) . . . . ?
F15 C54 C55 F16 -3.7(5) . . . . ?
C53 C54 C55 F16 176.5(3) . . . . ?
F15 C54 C55 C56 177.2(3) . . . . ?
C53 C54 C55 C56 -2.6(5) . . . . ?
F16 C55 C56 F17 0.8(5) . . . . ?
C54 C55 C56 F17 179.9(3) . . . . ?
F16 C55 C56 C51 -177.9(3) . . . . ?
C54 C55 C56 C51 1.2(5) . . . . ?
C52 C51 C56 F17 -177.0(3) . . . . ?
B1 C51 C56 F17 -4.6(5) . . . . ?
C52 C51 C56 C55 1.6(5) . . . . ?
B1 C51 C56 C55 174.1(3) . . . . ?
F2 C35 C57 F20 -2.3(5) . . . . ?
C36 C35 C57 F20 179.2(3) . . . . ?
F2 C35 C57 C58 178.6(3) . . . . ?
C36 C35 C57 C58 0.0(5) . . . . ?
C37 C38 C58 F21 -178.5(3) . . . . ?
B1 C38 C58 F21 -5.0(5) . . . . ?
C37 C38 C58 C57 1.3(5) . . . . ?
B1 C38 C58 C57 174.9(3) . . . . ?
F20 C57 C58 F21 -0.2(5) . . . . ?
C35 C57 C58 F21 179.0(3) . . . . ?
F20 C57 C58 C38 180.0(3) . . . . ?
C35 C57 C58 C38 -0.9(5) . . . . ?
C49 C39 B1 C38 -9.2(5) . . . . ?
C40 C39 B1 C38 -178.3(3) . . . . ?
C49 C39 B1 C46 112.3(3) . . . . ?
C40 C39 B1 C46 -56.7(4) . . . . ?
C49 C39 B1 C51 -125.4(3) . . . . ?
C40 C39 B1 C51 65.6(4) . . . . ?
C58 C38 B1 C39 124.7(3) . . . . ?
C37 C38 B1 C39 -62.2(4) . . . . ?
C58 C38 B1 C46 9.9(4) . . . . ?
C37 C38 B1 C46 -177.0(3) . . . . ?
C58 C38 B1 C51 -113.2(3) . . . . ?
C37 C38 B1 C51 59.9(4) . . . . ?
C47 C46 B1 C39 114.2(3) . . . . ?
C45 C46 B1 C39 -55.8(4) . . . . ?
C47 C46 B1 C38 -123.3(4) . . . . ?
C45 C46 B1 C38 66.8(4) . . . . ?
C47 C46 B1 C51 -7.1(5) . . . . ?
C45 C46 B1 C51 -177.0(3) . . . . ?
C52 C51 B1 C39 -176.6(3) . . . . ?
C56 C51 B1 C39 11.5(5) . . . . ?
C52 C51 B1 C38 60.2(4) . . . . ?
C56 C51 B1 C38 -111.7(4) . . . . ?
C52 C51 B1 C46 -62.1(4) . . . . ?
C56 C51 B1 C46 126.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_4_[(C10H6)(Ph2PF2)(Ph2PF)][B(C6F5)4]
_audit_block_doi                 10.5517/cc13ytrm
_database_code_depnum_ccdc_archive 'CCDC 1041561'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5SC00051C 2015
_audit_update_record             
;
2014-12-30 deposited with the CCDC.
2015-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 B F20, C34 H26 F3 P2, C1.25, H2.5 Cl2.5'
_chemical_formula_sum            'C59.25 H28.50 B Cl2.50 F23 P2'
_chemical_formula_weight         1338.70

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   18.8002(9)
_cell_length_b                   17.1372(10)
_cell_length_c                   17.8001(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.564(2)
_cell_angle_gamma                90.00
_cell_volume                     5597.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    149(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      4.689
_cell_measurement_theta_max      54.694

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2674
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6807
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
'SADABS. Area-Detector Integration Software. (Siemens Industrial Automation, 1995, Inc.: Madison, WI)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      149(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            50339
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         27.55
_reflns_number_total             12911
_reflns_number_gt                8842
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'Bruker SMART. Area-Detector Software Package. (Siemens Industrial Automation, 1993, Inc.: Madison, WI)'
_computing_cell_refinement       
'Bruker SMART. Area-Detector Software Package. (Siemens Industrial Automation, 1993, Inc.: Madison, WI)'
_computing_data_reduction        
'Bruker SAINT. Area-Detector Integration Software. (Siemens Industrial Automation, 1995, Inc.: Madison, WI)'
_computing_structure_solution    
'SHELX-97. Programs for Crystal Structure Analysis. (G. M. Sheldrick, 1997, Release 97-2, University of Gttingen, Germany)'
_computing_structure_refinement  
'SHELX-97. Programs for Crystal Structure Analysis. (G. M. Sheldrick, 1997, Release 97-2, University of Gttingen, Germany)'
_computing_molecular_graphics    
'Ortep for Windows (L. J. Farrugia, J. Appl. Cryst. 1997, 30, 565)'
_computing_publication_material  
'WinGX v1.70.01 (L. J. Farrugia, J. Appl. Cryst. 1999, 32, 837)'


_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)+(0.0638P)²+0.0000P] 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         12911
_refine_ls_number_parameters     757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.57756(11) 0.71553(15) 0.95892(12) 0.0316(5) Uani 1 1 d . . .
H2 H 0.5810 0.7065 0.9072 0.038 Uiso 1 1 calc R . .
C3 C 0.50914(11) 0.73357(16) 0.97355(14) 0.0385(6) Uani 1 1 d . . .
H3 H 0.4682 0.7408 0.9322 0.046 Uiso 1 1 calc R . .
C4 C 0.50195(11) 0.74057(16) 1.04677(15) 0.0432(7) Uani 1 1 d . . .
H4 H 0.4551 0.7490 1.0571 0.052 Uiso 1 1 calc R . .
C5 C 0.56346(11) 0.73556(16) 1.10864(13) 0.0377(6) Uani 1 1 d . . .
C6 C 0.63501(10) 0.72812(13) 1.09385(11) 0.0239(4) Uani 1 1 d . . .
C7 C 0.69331(10) 0.74076(13) 1.15934(11) 0.0246(5) Uani 1 1 d . . .
C8 C 0.68128(12) 0.74484(17) 1.23285(13) 0.0417(7) Uani 1 1 d . . .
H8 H 0.7214 0.7526 1.2750 0.050 Uiso 1 1 calc R . .
C9 C 0.61116(13) 0.7377(2) 1.24656(15) 0.0663(11) Uani 1 1 d . . .
H9 H 0.6037 0.7334 1.2975 0.080 Uiso 1 1 calc R . .
C10 C 0.55401(13) 0.7371(2) 1.18505(16) 0.0628(10) Uani 1 1 d . . .
H10 H 0.5059 0.7376 1.1938 0.075 Uiso 1 1 calc R . .
C11 C 0.67256(10) 0.55925(14) 0.94818(11) 0.0245(5) Uani 1 1 d . . .
C12 C 0.62766(11) 0.51767(14) 0.98552(12) 0.0291(5) Uani 1 1 d . . .
H12 H 0.6181 0.5370 1.0324 0.035 Uiso 1 1 calc R . .
C13 C 0.59641(12) 0.44823(15) 0.95543(14) 0.0381(6) Uani 1 1 d . . .
H13 H 0.5645 0.4207 0.9807 0.046 Uiso 1 1 calc R . .
C14 C 0.61174(13) 0.41923(16) 0.88864(15) 0.0458(7) Uani 1 1 d . . .
H14 H 0.5908 0.3713 0.8680 0.055 Uiso 1 1 calc R . .
C15 C 0.65677(15) 0.45901(19) 0.85221(16) 0.0548(8) Uani 1 1 d . . .
H15 H 0.6678 0.4381 0.8066 0.066 Uiso 1 1 calc R . .
C16 C 0.68684(13) 0.52958(16) 0.88059(13) 0.0417(6) Uani 1 1 d . . .
H16 H 0.7172 0.5576 0.8538 0.050 Uiso 1 1 calc R . .
C17 C 0.80883(10) 0.65924(13) 0.98785(11) 0.0235(5) Uani 1 1 d . . .
C18 C 0.85465(10) 0.60040(14) 1.02281(12) 0.0294(5) Uani 1 1 d . . .
H18 H 0.8360 0.5594 1.0489 0.035 Uiso 1 1 calc R . .
C19 C 0.92815(12) 0.60114(16) 1.01977(14) 0.0403(6) Uani 1 1 d . . .
H19 H 0.9591 0.5597 1.0424 0.048 Uiso 1 1 calc R . .
C20 C 0.95601(12) 0.66125(19) 0.98432(14) 0.0463(7) Uani 1 1 d . . .
H20 H 1.0063 0.6617 0.9830 0.056 Uiso 1 1 calc R . .
C21 C 0.91142(13) 0.72095(18) 0.95061(14) 0.0456(7) Uani 1 1 d . . .
H21 H 0.9312 0.7630 0.9271 0.055 Uiso 1 1 calc R . .
C22 C 0.83699(12) 0.72001(15) 0.95078(12) 0.0325(5) Uani 1 1 d . . .
H22 H 0.8059 0.7603 0.9259 0.039 Uiso 1 1 calc R . .
C23 C 0.85532(10) 0.70960(12) 1.18620(11) 0.0213(4) Uani 1 1 d . . .
C24 C 0.92325(10) 0.72995(13) 1.17276(11) 0.0254(5) Uani 1 1 d . . .
H24 H 0.9291 0.7765 1.1458 0.031 Uiso 1 1 calc R . .
C25 C 0.98205(11) 0.68129(15) 1.19932(13) 0.0337(5) Uani 1 1 d . . .
H25 H 1.0283 0.6935 1.1891 0.040 Uiso 1 1 calc R . .
C26 C 0.97366(12) 0.61570(16) 1.24023(14) 0.0424(6) Uani 1 1 d . . .
H26 H 1.0147 0.5834 1.2594 0.051 Uiso 1 1 calc R . .
C27 C 0.90655(13) 0.59555(15) 1.25423(15) 0.0446(6) Uani 1 1 d . . .
H27 H 0.9017 0.5499 1.2829 0.053 Uiso 1 1 calc R . .
C28 C 0.84632(11) 0.64211(14) 1.22633(12) 0.0315(5) Uani 1 1 d . . .
H28 H 0.7997 0.6281 1.2345 0.038 Uiso 1 1 calc R . .
C29 C 0.79903(10) 0.86486(12) 1.20277(11) 0.0221(4) Uani 1 1 d . . .
C30 C 0.75469(12) 0.92762(14) 1.17419(12) 0.0323(5) Uani 1 1 d . . .
H30 H 0.7150 0.9207 1.1315 0.039 Uiso 1 1 calc R . .
C31 C 0.76845(14) 1.00026(15) 1.20796(14) 0.0401(6) Uani 1 1 d . . .
H31 H 0.7391 1.0437 1.1876 0.048 Uiso 1 1 calc R . .
C32 C 0.82496(13) 1.00939(16) 1.27128(14) 0.0413(6) Uani 1 1 d . . .
H32 H 0.8342 1.0592 1.2947 0.050 Uiso 1 1 calc R . .
C33 C 0.86783(13) 0.94727(16) 1.30068(14) 0.0408(6) Uani 1 1 d . . .
H33 H 0.9061 0.9542 1.3448 0.049 Uiso 1 1 calc R . .
C34 C 0.85577(11) 0.87434(14) 1.26661(12) 0.0303(5) Uani 1 1 d . . .
H34 H 0.8859 0.8314 1.2867 0.036 Uiso 1 1 calc R . .
C35 C 0.83487(9) 0.30277(12) 0.28425(10) 0.0175(4) Uani 1 1 d . . .
C36 C 0.89027(9) 0.34517(12) 0.26262(10) 0.0189(4) Uani 1 1 d . . .
C37 C 0.91871(10) 0.32753(13) 0.19946(11) 0.0232(4) Uani 1 1 d . . .
C38 C 0.89322(11) 0.26460(14) 0.15457(11) 0.0257(5) Uani 1 1 d . . .
C39 C 0.83854(11) 0.22043(13) 0.17237(10) 0.0238(4) Uani 1 1 d . . .
C40 C 0.81058(10) 0.24091(12) 0.23488(10) 0.0204(4) Uani 1 1 d . . .
C41 C 0.83453(10) 0.39008(12) 0.41566(10) 0.0204(4) Uani 1 1 d . . .
C42 C 0.80557(11) 0.45559(14) 0.44291(11) 0.0275(5) Uani 1 1 d . . .
C43 C 0.84241(14) 0.50209(14) 0.50210(13) 0.0368(6) Uani 1 1 d . . .
C44 C 0.91175(13) 0.48255(15) 0.53920(12) 0.0369(6) Uani 1 1 d . . .
C45 C 0.94377(12) 0.41807(14) 0.51556(12) 0.0299(5) Uani 1 1 d . . .
C46 C 0.90509(10) 0.37434(13) 0.45561(10) 0.0227(4) Uani 1 1 d . . .
C47 C 0.77852(9) 0.25452(12) 0.40811(10) 0.0193(4) Uani 1 1 d . . .
C48 C 0.73092(10) 0.26172(14) 0.45752(11) 0.0243(5) Uani 1 1 d . . .
C49 C 0.72492(11) 0.20885(15) 0.51403(11) 0.0307(5) Uani 1 1 d . . .
C50 C 0.76843(11) 0.14445(15) 0.52532(11) 0.0314(5) Uani 1 1 d . . .
C51 C 0.81685(11) 0.13341(14) 0.47861(12) 0.0295(5) Uani 1 1 d . . .
C52 C 0.82039(10) 0.18793(13) 0.42201(11) 0.0225(4) Uani 1 1 d . . .
C53 C 0.71497(9) 0.36278(13) 0.29720(10) 0.0211(4) Uani 1 1 d . . .
C54 C 0.71642(10) 0.43332(13) 0.25993(11) 0.0252(5) Uani 1 1 d . . .
C55 C 0.65855(11) 0.46610(15) 0.20909(12) 0.0340(6) Uani 1 1 d . . .
C56 C 0.59436(11) 0.42509(18) 0.18986(12) 0.0416(7) Uani 1 1 d . . .
C57 C 0.58976(11) 0.35441(17) 0.22352(12) 0.0381(6) Uani 1 1 d . . .
C58 C 0.64866(10) 0.32462(14) 0.27624(11) 0.0272(5) Uani 1 1 d . . .
XC1 C 0.64001(10) 0.71028(13) 1.01579(11) 0.0227(4) Uani 1 1 d . . .
B1 B 0.79062(10) 0.32743(14) 0.35150(12) 0.0174(4) Uani 1 1 d . . .
F1 F 0.73246(5) 0.61636(7) 1.07606(6) 0.0220(3) Uani 1 1 d . . .
F2 F 0.69394(6) 0.69399(8) 0.90072(6) 0.0315(3) Uani 1 1 d . . .
F3 F 0.77745(6) 0.79434(7) 1.06990(6) 0.0245(3) Uani 1 1 d . . .
F4 F 0.92018(6) 0.40784(7) 0.30368(6) 0.0258(3) Uani 1 1 d . . .
F5 F 0.97219(6) 0.37175(9) 0.18217(7) 0.0366(3) Uani 1 1 d . . .
F6 F 0.92191(7) 0.24560(9) 0.09386(7) 0.0384(3) Uani 1 1 d . . .
F7 F 0.81252(7) 0.15832(8) 0.12854(7) 0.0364(3) Uani 1 1 d . . .
F8 F 0.75516(6) 0.19591(7) 0.24808(6) 0.0287(3) Uani 1 1 d . . .
F9 F 0.73647(7) 0.47906(9) 0.41182(7) 0.0414(3) Uani 1 1 d . . .
F10 F 0.81078(9) 0.56627(9) 0.52317(9) 0.0593(4) Uani 1 1 d . . .
F11 F 0.94817(9) 0.52672(10) 0.59768(8) 0.0584(5) Uani 1 1 d . . .
F12 F 1.01174(7) 0.39842(9) 0.55144(7) 0.0441(4) Uani 1 1 d . . .
F13 F 0.94006(6) 0.31098(7) 0.43614(6) 0.0277(3) Uani 1 1 d . . .
F14 F 0.68757(6) 0.32597(8) 0.45199(7) 0.0350(3) Uani 1 1 d . . .
F15 F 0.67737(6) 0.22140(10) 0.56001(7) 0.0445(4) Uani 1 1 d . . .
F16 F 0.76467(7) 0.09286(9) 0.58101(7) 0.0470(4) Uani 1 1 d . . .
F17 F 0.86159(8) 0.07143(8) 0.48861(8) 0.0449(4) Uani 1 1 d . . .
F18 F 0.87110(6) 0.17138(7) 0.38021(6) 0.0272(3) Uani 1 1 d . . .
F19 F 0.77875(6) 0.47564(7) 0.27302(7) 0.0311(3) Uani 1 1 d . . .
F20 F 0.66390(7) 0.53686(9) 0.17889(8) 0.0480(4) Uani 1 1 d . . .
F21 F 0.53699(7) 0.45454(12) 0.13944(8) 0.0662(5) Uani 1 1 d . . .
F22 F 0.52737(7) 0.31305(11) 0.20487(8) 0.0596(5) Uani 1 1 d . . .
F23 F 0.63755(6) 0.25436(8) 0.30631(7) 0.0358(3) Uani 1 1 d . . .
P1 P 0.71156(2) 0.65091(3) 0.98677(3) 0.01941(12) Uani 1 1 d . . .
P2 P 0.78167(2) 0.77402(3) 1.15518(3) 0.01909(12) 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
C2 XC1 1.376(3) . ?
C2 C3 1.401(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.345(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.415(3) . ?
C4 H4 0.9500 . ?
C5 C10 1.410(3) . ?
C5 C6 1.431(3) . ?
C6 C7 1.432(3) . ?
C6 XC1 1.446(3) . ?
C7 C8 1.377(3) . ?
C7 P2 1.7730(19) . ?
C8 C9 1.397(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.357(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.381(3) . ?
C11 C16 1.385(3) . ?
C11 P1 1.805(2) . ?
C12 C13 1.382(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.376(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.357(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.383(3) . ?
C17 C22 1.397(3) . ?
C17 P1 1.8303(19) . ?
C18 C19 1.395(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.370(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.400(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.389(3) . ?
C23 C24 1.394(3) . ?
C23 P2 1.763(2) . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.367(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.382(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.386(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C34 1.389(3) . ?
C29 C30 1.388(3) . ?
C29 P2 1.768(2) . ?
C30 C31 1.382(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.379(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.369(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.386(3) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C40 1.389(3) . ?
C35 C36 1.391(3) . ?
C35 B1 1.654(3) . ?
C36 F4 1.351(2) . ?
C36 C37 1.379(3) . ?
C37 F5 1.347(2) . ?
C37 C38 1.366(3) . ?
C38 F6 1.349(2) . ?
C38 C39 1.368(3) . ?
C39 F7 1.347(2) . ?
C39 C40 1.376(3) . ?
C40 F8 1.357(2) . ?
C41 C42 1.381(3) . ?
C41 C46 1.388(3) . ?
C41 B1 1.652(3) . ?
C42 F9 1.357(2) . ?
C42 C43 1.381(3) . ?
C43 F10 1.342(3) . ?
C43 C44 1.369(3) . ?
C44 F11 1.347(2) . ?
C44 C45 1.368(3) . ?
C45 F12 1.341(2) . ?
C45 C46 1.375(3) . ?
C46 F13 1.353(2) . ?
C47 C52 1.378(3) . ?
C47 C48 1.390(3) . ?
C47 B1 1.652(3) . ?
C48 F14 1.361(2) . ?
C48 C49 1.376(3) . ?
C49 F15 1.354(2) . ?
C49 C50 1.362(3) . ?
C50 F16 1.342(2) . ?
C50 C51 1.373(3) . ?
C51 F17 1.342(3) . ?
C51 C52 1.386(3) . ?
C52 F18 1.361(2) . ?
C53 C54 1.382(3) . ?
C53 C58 1.385(3) . ?
C53 B1 1.651(3) . ?
C54 F19 1.354(2) . ?
C54 C55 1.375(3) . ?
C55 F20 1.339(3) . ?
C55 C56 1.374(3) . ?
C56 F21 1.343(2) . ?
C56 C57 1.362(4) . ?
C57 F22 1.349(2) . ?
C57 C58 1.384(3) . ?
C58 F23 1.352(3) . ?
XC1 P1 1.848(2) . ?
F1 P1 1.6610(11) . ?
F2 P1 1.6674(12) . ?
F3 P2 1.5426(11) . ?

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
XC1 C2 C3 123.3(2) . . ?
XC1 C2 H2 118.4 . . ?
C3 C2 H2 118.4 . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C10 C5 C4 119.8(2) . . ?
C10 C5 C6 120.0(2) . . ?
C4 C5 C6 120.2(2) . . ?
C5 C6 C7 114.85(17) . . ?
C5 C6 XC1 117.12(17) . . ?
C7 C6 XC1 128.03(16) . . ?
C8 C7 C6 121.75(17) . . ?
C8 C7 P2 111.86(15) . . ?
C6 C7 P2 124.94(15) . . ?
C7 C8 C9 121.2(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 118.1(2) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C9 C10 C5 122.3(2) . . ?
C9 C10 H10 118.8 . . ?
C5 C10 H10 118.8 . . ?
C12 C11 C16 118.9(2) . . ?
C12 C11 P1 120.41(15) . . ?
C16 C11 P1 120.71(17) . . ?
C11 C12 C13 120.7(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 119.8(2) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C18 C17 C22 119.54(19) . . ?
C18 C17 P1 118.09(16) . . ?
C22 C17 P1 122.25(17) . . ?
C17 C18 C19 120.1(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.4(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 119.4(2) . . ?
C17 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C28 C23 C24 121.01(19) . . ?
C28 C23 P2 120.48(15) . . ?
C24 C23 P2 118.43(16) . . ?
C25 C24 C23 119.0(2) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C26 C25 C24 120.1(2) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 121.1(2) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C26 C27 C28 119.9(2) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C27 C28 C23 118.8(2) . . ?
C27 C28 H28 120.6 . . ?
C23 C28 H28 120.6 . . ?
C34 C29 C30 120.2(2) . . ?
C34 C29 P2 121.58(17) . . ?
C30 C29 P2 118.24(15) . . ?
C31 C30 C29 119.9(2) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C32 119.7(2) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C33 C32 C31 120.6(2) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C32 C33 C34 120.5(2) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C29 C34 C33 119.1(2) . . ?
C29 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C40 C35 C36 112.73(16) . . ?
C40 C35 B1 120.32(16) . . ?
C36 C35 B1 126.26(17) . . ?
F4 C36 C37 115.19(16) . . ?
F4 C36 C35 120.94(16) . . ?
C37 C36 C35 123.87(19) . . ?
F5 C37 C38 119.67(17) . . ?
F5 C37 C36 120.26(19) . . ?
C38 C37 C36 120.07(18) . . ?
F6 C38 C39 120.2(2) . . ?
F6 C38 C37 120.59(19) . . ?
C39 C38 C37 119.16(17) . . ?
F7 C39 C38 119.97(17) . . ?
F7 C39 C40 121.04(18) . . ?
C38 C39 C40 119.00(19) . . ?
F8 C40 C39 115.97(17) . . ?
F8 C40 C35 118.89(16) . . ?
C39 C40 C35 125.14(18) . . ?
C42 C41 C46 112.57(18) . . ?
C42 C41 B1 126.54(17) . . ?
C46 C41 B1 120.40(18) . . ?
F9 C42 C43 114.6(2) . . ?
F9 C42 C41 120.87(18) . . ?
C43 C42 C41 124.5(2) . . ?
F10 C43 C44 119.9(2) . . ?
F10 C43 C42 120.5(2) . . ?
C44 C43 C42 119.6(2) . . ?
F11 C44 C45 120.5(2) . . ?
F11 C44 C43 120.4(2) . . ?
C45 C44 C43 119.1(2) . . ?
F12 C45 C44 119.59(19) . . ?
F12 C45 C46 121.4(2) . . ?
C44 C45 C46 119.0(2) . . ?
F13 C46 C45 115.58(18) . . ?
F13 C46 C41 119.21(17) . . ?
C45 C46 C41 125.2(2) . . ?
C52 C47 C48 112.41(18) . . ?
C52 C47 B1 125.93(16) . . ?
C48 C47 B1 120.80(18) . . ?
F14 C48 C49 116.26(17) . . ?
F14 C48 C47 118.94(18) . . ?
C49 C48 C47 124.8(2) . . ?
F15 C49 C50 119.58(19) . . ?
F15 C49 C48 120.5(2) . . ?
C50 C49 C48 119.93(19) . . ?
F16 C50 C49 121.1(2) . . ?
F16 C50 C51 120.3(2) . . ?
C49 C50 C51 118.57(19) . . ?
F17 C51 C50 120.51(19) . . ?
F17 C51 C52 120.12(19) . . ?
C50 C51 C52 119.4(2) . . ?
F18 C52 C47 121.02(17) . . ?
F18 C52 C51 114.02(18) . . ?
C47 C52 C51 124.94(18) . . ?
C54 C53 C58 113.22(17) . . ?
C54 C53 B1 119.84(16) . . ?
C58 C53 B1 126.49(19) . . ?
F19 C54 C55 115.20(19) . . ?
F19 C54 C53 119.50(17) . . ?
C55 C54 C53 125.30(19) . . ?
F20 C55 C56 120.1(2) . . ?
F20 C55 C54 121.1(2) . . ?
C56 C55 C54 118.8(2) . . ?
F21 C56 C57 120.6(2) . . ?
F21 C56 C55 120.6(2) . . ?
C57 C56 C55 118.79(19) . . ?
F22 C57 C56 119.60(19) . . ?
F22 C57 C58 119.9(2) . . ?
C56 C57 C58 120.5(2) . . ?
F23 C58 C53 121.41(18) . . ?
F23 C58 C57 115.29(18) . . ?
C53 C58 C57 123.3(2) . . ?
C2 XC1 C6 118.01(17) . . ?
C2 XC1 P1 112.76(15) . . ?
C6 XC1 P1 126.07(14) . . ?
C41 B1 C53 113.80(17) . . ?
C41 B1 C47 100.62(14) . . ?
C53 B1 C47 114.79(15) . . ?
C41 B1 C35 114.33(15) . . ?
C53 B1 C35 100.07(14) . . ?
C47 B1 C35 113.95(17) . . ?
F1 P1 F2 174.35(7) . . ?
F1 P1 C11 92.63(8) . . ?
F2 P1 C11 93.01(8) . . ?
F1 P1 C17 89.42(7) . . ?
F2 P1 C17 88.48(8) . . ?
C11 P1 C17 113.21(9) . . ?
F1 P1 XC1 87.93(7) . . ?
F2 P1 XC1 90.10(8) . . ?
C11 P1 XC1 109.00(9) . . ?
C17 P1 XC1 137.79(10) . . ?
F3 P2 C23 108.56(8) . . ?
F3 P2 C29 103.72(8) . . ?
C23 P2 C29 110.53(9) . . ?
F3 P2 C7 105.40(8) . . ?
C23 P2 C7 117.70(10) . . ?
C29 P2 C7 109.87(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
XC1 C2 C3 C4 -5.2(4) . . . . ?
C2 C3 C4 C5 4.6(4) . . . . ?
C3 C4 C5 C10 -175.1(3) . . . . ?
C3 C4 C5 C6 4.2(4) . . . . ?
C10 C5 C6 C7 -13.8(4) . . . . ?
C4 C5 C6 C7 166.9(2) . . . . ?
C10 C5 C6 XC1 167.1(3) . . . . ?
C4 C5 C6 XC1 -12.2(4) . . . . ?
C5 C6 C7 C8 11.8(3) . . . . ?
XC1 C6 C7 C8 -169.3(2) . . . . ?
C5 C6 C7 P2 -153.35(19) . . . . ?
XC1 C6 C7 P2 25.6(3) . . . . ?
C6 C7 C8 C9 -0.8(4) . . . . ?
P2 C7 C8 C9 166.1(3) . . . . ?
C7 C8 C9 C10 -8.6(5) . . . . ?
C8 C9 C10 C5 6.4(5) . . . . ?
C4 C5 C10 C9 -175.5(3) . . . . ?
C6 C5 C10 C9 5.2(5) . . . . ?
C16 C11 C12 C13 -1.1(3) . . . . ?
P1 C11 C12 C13 178.65(17) . . . . ?
C11 C12 C13 C14 1.7(3) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
C13 C14 C15 C16 -1.1(4) . . . . ?
C14 C15 C16 C11 1.8(4) . . . . ?
C12 C11 C16 C15 -0.6(4) . . . . ?
P1 C11 C16 C15 179.6(2) . . . . ?
C22 C17 C18 C19 -1.2(3) . . . . ?
P1 C17 C18 C19 174.98(16) . . . . ?
C17 C18 C19 C20 2.1(3) . . . . ?
C18 C19 C20 C21 -0.8(4) . . . . ?
C19 C20 C21 C22 -1.3(4) . . . . ?
C18 C17 C22 C21 -0.9(3) . . . . ?
P1 C17 C22 C21 -176.91(16) . . . . ?
C20 C21 C22 C17 2.2(3) . . . . ?
C28 C23 C24 C25 0.7(3) . . . . ?
P2 C23 C24 C25 177.65(16) . . . . ?
C23 C24 C25 C26 -2.1(3) . . . . ?
C24 C25 C26 C27 1.6(4) . . . . ?
C25 C26 C27 C28 0.2(4) . . . . ?
C26 C27 C28 C23 -1.6(4) . . . . ?
C24 C23 C28 C27 1.1(3) . . . . ?
P2 C23 C28 C27 -175.76(18) . . . . ?
C34 C29 C30 C31 2.0(3) . . . . ?
P2 C29 C30 C31 -177.36(17) . . . . ?
C29 C30 C31 C32 -1.9(3) . . . . ?
C30 C31 C32 C33 0.4(4) . . . . ?
C31 C32 C33 C34 0.9(4) . . . . ?
C30 C29 C34 C33 -0.7(3) . . . . ?
P2 C29 C34 C33 178.66(17) . . . . ?
C32 C33 C34 C29 -0.8(3) . . . . ?
C40 C35 C36 F4 179.48(16) . . . . ?
B1 C35 C36 F4 9.1(3) . . . . ?
C40 C35 C36 C37 -0.6(3) . . . . ?
B1 C35 C36 C37 -170.95(18) . . . . ?
F4 C36 C37 F5 -0.3(3) . . . . ?
C35 C36 C37 F5 179.71(17) . . . . ?
F4 C36 C37 C38 179.01(17) . . . . ?
C35 C36 C37 C38 -0.9(3) . . . . ?
F5 C37 C38 F6 1.1(3) . . . . ?
C36 C37 C38 F6 -178.26(17) . . . . ?
F5 C37 C38 C39 -179.55(18) . . . . ?
C36 C37 C38 C39 1.1(3) . . . . ?
F6 C38 C39 F7 -0.9(3) . . . . ?
C37 C38 C39 F7 179.74(18) . . . . ?
F6 C38 C39 C40 179.63(17) . . . . ?
C37 C38 C39 C40 0.3(3) . . . . ?
F7 C39 C40 F8 -1.2(3) . . . . ?
C38 C39 C40 F8 178.29(17) . . . . ?
F7 C39 C40 C35 178.55(18) . . . . ?
C38 C39 C40 C35 -2.0(3) . . . . ?
C36 C35 C40 F8 -178.22(16) . . . . ?
B1 C35 C40 F8 -7.2(3) . . . . ?
C36 C35 C40 C39 2.1(3) . . . . ?
B1 C35 C40 C39 173.07(18) . . . . ?
C46 C41 C42 F9 -178.65(18) . . . . ?
B1 C41 C42 F9 -6.8(3) . . . . ?
C46 C41 C42 C43 1.4(3) . . . . ?
B1 C41 C42 C43 173.3(2) . . . . ?
F9 C42 C43 F10 -2.2(3) . . . . ?
C41 C42 C43 F10 177.8(2) . . . . ?
F9 C42 C43 C44 178.1(2) . . . . ?
C41 C42 C43 C44 -2.0(4) . . . . ?
F10 C43 C44 F11 1.0(3) . . . . ?
C42 C43 C44 F11 -179.2(2) . . . . ?
F10 C43 C44 C45 -178.3(2) . . . . ?
C42 C43 C44 C45 1.5(3) . . . . ?
F11 C44 C45 F12 0.6(3) . . . . ?
C43 C44 C45 F12 179.9(2) . . . . ?
F11 C44 C45 C46 -179.9(2) . . . . ?
C43 C44 C45 C46 -0.6(3) . . . . ?
F12 C45 C46 F13 0.2(3) . . . . ?
C44 C45 C46 F13 -179.24(18) . . . . ?
F12 C45 C46 C41 179.56(19) . . . . ?
C44 C45 C46 C41 0.1(3) . . . . ?
C42 C41 C46 F13 178.86(17) . . . . ?
B1 C41 C46 F13 6.4(3) . . . . ?
C42 C41 C46 C45 -0.4(3) . . . . ?
B1 C41 C46 C45 -172.87(19) . . . . ?
C52 C47 C48 F14 178.08(17) . . . . ?
B1 C47 C48 F14 8.1(3) . . . . ?
C52 C47 C48 C49 -0.4(3) . . . . ?
B1 C47 C48 C49 -170.44(18) . . . . ?
F14 C48 C49 F15 0.7(3) . . . . ?
C47 C48 C49 F15 179.26(18) . . . . ?
F14 C48 C49 C50 -177.48(18) . . . . ?
C47 C48 C49 C50 1.1(3) . . . . ?
F15 C49 C50 F16 0.4(3) . . . . ?
C48 C49 C50 F16 178.65(18) . . . . ?
F15 C49 C50 C51 -179.22(18) . . . . ?
C48 C49 C50 C51 -1.0(3) . . . . ?
F16 C50 C51 F17 -0.8(3) . . . . ?
C49 C50 C51 F17 178.86(19) . . . . ?
F16 C50 C51 C52 -179.25(18) . . . . ?
C49 C50 C51 C52 0.4(3) . . . . ?
C48 C47 C52 F18 -178.94(16) . . . . ?
B1 C47 C52 F18 -9.5(3) . . . . ?
C48 C47 C52 C51 -0.2(3) . . . . ?
B1 C47 C52 C51 169.18(18) . . . . ?
F17 C51 C52 F18 0.5(3) . . . . ?
C50 C51 C52 F18 179.03(17) . . . . ?
F17 C51 C52 C47 -178.24(18) . . . . ?
C50 C51 C52 C47 0.2(3) . . . . ?
C58 C53 C54 F19 -177.77(17) . . . . ?
B1 C53 C54 F19 -5.0(3) . . . . ?
C58 C53 C54 C55 2.4(3) . . . . ?
B1 C53 C54 C55 175.2(2) . . . . ?
F19 C54 C55 F20 -3.5(3) . . . . ?
C53 C54 C55 F20 176.3(2) . . . . ?
F19 C54 C55 C56 176.9(2) . . . . ?
C53 C54 C55 C56 -3.3(4) . . . . ?
F20 C55 C56 F21 1.5(4) . . . . ?
C54 C55 C56 F21 -178.9(2) . . . . ?
F20 C55 C56 C57 -177.8(2) . . . . ?
C54 C55 C56 C57 1.8(4) . . . . ?
F21 C56 C57 F22 1.2(4) . . . . ?
C55 C56 C57 F22 -179.5(2) . . . . ?
F21 C56 C57 C58 -179.1(2) . . . . ?
C55 C56 C57 C58 0.1(4) . . . . ?
C54 C53 C58 F23 179.27(18) . . . . ?
B1 C53 C58 F23 7.1(3) . . . . ?
C54 C53 C58 C57 -0.3(3) . . . . ?
B1 C53 C58 C57 -172.4(2) . . . . ?
F22 C57 C58 F23 -0.9(3) . . . . ?
C56 C57 C58 F23 179.5(2) . . . . ?
F22 C57 C58 C53 178.7(2) . . . . ?
C56 C57 C58 C53 -0.9(4) . . . . ?
C3 C2 XC1 C6 -3.2(4) . . . . ?
C3 C2 XC1 P1 158.0(2) . . . . ?
C5 C6 XC1 C2 11.5(3) . . . . ?
C7 C6 XC1 C2 -167.4(2) . . . . ?
C5 C6 XC1 P1 -146.88(19) . . . . ?
C7 C6 XC1 P1 34.2(3) . . . . ?
C42 C41 B1 C53 20.6(3) . . . . ?
C46 C41 B1 C53 -168.13(17) . . . . ?
C42 C41 B1 C47 -102.7(2) . . . . ?
C46 C41 B1 C47 68.6(2) . . . . ?
C42 C41 B1 C35 134.7(2) . . . . ?
C46 C41 B1 C35 -54.0(2) . . . . ?
C54 C53 B1 C41 51.3(2) . . . . ?
C58 C53 B1 C41 -137.0(2) . . . . ?
C54 C53 B1 C47 166.47(17) . . . . ?
C58 C53 B1 C47 -21.9(3) . . . . ?
C54 C53 B1 C35 -71.1(2) . . . . ?
C58 C53 B1 C35 100.6(2) . . . . ?
C52 C47 B1 C41 -99.1(2) . . . . ?
C48 C47 B1 C41 69.5(2) . . . . ?
C52 C47 B1 C53 138.29(19) . . . . ?
C48 C47 B1 C53 -53.1(2) . . . . ?
C52 C47 B1 C35 23.7(3) . . . . ?
C48 C47 B1 C35 -167.69(16) . . . . ?
C40 C35 B1 C41 168.75(17) . . . . ?
C36 C35 B1 C41 -21.5(3) . . . . ?
C40 C35 B1 C53 -69.2(2) . . . . ?
C36 C35 B1 C53 100.5(2) . . . . ?
C40 C35 B1 C47 53.8(2) . . . . ?
C36 C35 B1 C47 -136.51(18) . . . . ?
C12 C11 P1 F1 43.43(17) . . . . ?
C16 C11 P1 F1 -136.84(18) . . . . ?
C12 C11 P1 F2 -136.44(17) . . . . ?
C16 C11 P1 F2 43.29(19) . . . . ?
C12 C11 P1 C17 133.93(17) . . . . ?
C16 C11 P1 C17 -46.3(2) . . . . ?
C12 C11 P1 XC1 -45.29(19) . . . . ?
C16 C11 P1 XC1 134.44(18) . . . . ?
C18 C17 P1 F1 39.54(16) . . . . ?
C22 C17 P1 F1 -144.42(17) . . . . ?
C18 C17 P1 F2 -145.70(16) . . . . ?
C22 C17 P1 F2 30.34(17) . . . . ?
C18 C17 P1 C11 -53.07(18) . . . . ?
C22 C17 P1 C11 122.96(18) . . . . ?
C18 C17 P1 XC1 125.83(17) . . . . ?
C22 C17 P1 XC1 -58.1(2) . . . . ?
C2 XC1 P1 F1 -142.12(17) . . . . ?
C6 XC1 P1 F1 17.20(18) . . . . ?
C2 XC1 P1 F2 43.17(17) . . . . ?
C6 XC1 P1 F2 -157.50(18) . . . . ?
C2 XC1 P1 C11 -50.05(19) . . . . ?
C6 XC1 P1 C11 109.28(18) . . . . ?
C2 XC1 P1 C17 131.02(17) . . . . ?
C6 XC1 P1 C17 -69.7(2) . . . . ?
C28 C23 P2 F3 -132.00(16) . . . . ?
C24 C23 P2 F3 51.05(17) . . . . ?
C28 C23 P2 C29 114.86(18) . . . . ?
C24 C23 P2 C29 -62.09(17) . . . . ?
C28 C23 P2 C7 -12.5(2) . . . . ?
C24 C23 P2 C7 170.57(15) . . . . ?
C34 C29 P2 F3 -128.98(16) . . . . ?
C30 C29 P2 F3 50.35(17) . . . . ?
C34 C29 P2 C23 -12.79(19) . . . . ?
C30 C29 P2 C23 166.54(16) . . . . ?
C34 C29 P2 C7 118.75(17) . . . . ?
C30 C29 P2 C7 -61.92(18) . . . . ?
C8 C7 P2 F3 -159.97(18) . . . . ?
C6 C7 P2 F3 6.4(2) . . . . ?
C8 C7 P2 C23 78.9(2) . . . . ?
C6 C7 P2 C23 -114.7(2) . . . . ?
C8 C7 P2 C29 -48.8(2) . . . . ?
C6 C7 P2 C29 117.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.055
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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 0.000 426 99 ' '
2 0.500 0.500 0.500 425 99 ' '
_platon_squeeze_details          
;
The unit cell contains 5 methylene chloride molecules 
which have been treated as a diffuse contribution to the 
overall scattering without specific atom positions by 
SQUEEZE/PLATON.
;
