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

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

data_pphi
_database_code_depnum_ccdc_archive 'CCDC 1545875'
_audit_update_record             
;
2017-04-25 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        YK_PPh_I
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H20 P, I, C H2 Cl2'
_chemical_formula_sum            'C27 H22 Cl2 I P'
_chemical_formula_weight         575.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
I I -0.4742 1.8119 '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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_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                   9.8866(2)
_cell_length_b                   21.0534(5)
_cell_length_c                   12.0079(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.878(2)
_cell_angle_gamma                90.00
_cell_volume                     2490.35(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    48571
_cell_measurement_theta_min      1.93
_cell_measurement_theta_max      26.5

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144
_exptl_absorpt_coefficient_mu    1.577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8842
_exptl_absorpt_correction_T_max  0.9542
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 Blessing, R. H., Acta Cryst., A51, 33-38 (1995).
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            48571
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         26.50
_reflns_number_total             5168
_reflns_number_gt                3904
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 '
_computing_molecular_graphics    'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)'
_computing_publication_material  
;Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)
;

_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)+(0.0348P)²+5.5212P] 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         5168
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.002
_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 0.41104(10) 0.19503(5) 0.23087(9) 0.0192(2) Uani 1 1 d . . .
C1 C 0.4468(4) 0.27903(19) 0.2164(3) 0.0224(9) Uani 1 1 d . . .
C2 C 0.3422(4) 0.3109(2) 0.2534(3) 0.0252(9) Uani 1 1 d . . .
H1 H 0.3412 0.3560 0.2558 0.030 Uiso 1 1 calc R . .
C3 C 0.2286(4) 0.2729(2) 0.2902(3) 0.0242(9) Uani 1 1 d . . .
C4 C 0.2491(4) 0.20733(19) 0.2845(3) 0.0213(8) Uani 1 1 d . . .
C5 C 0.1539(4) 0.1642(2) 0.3144(3) 0.0236(9) Uani 1 1 d . . .
H2 H 0.1691 0.1197 0.3099 0.028 Uiso 1 1 calc R . .
C6 C 0.0336(4) 0.1885(2) 0.3519(3) 0.0267(10) Uani 1 1 d . . .
H3 H -0.0337 0.1601 0.3742 0.032 Uiso 1 1 calc R . .
C7 C 0.0119(4) 0.2530(2) 0.3568(4) 0.0295(10) Uani 1 1 d . . .
H4 H -0.0705 0.2684 0.3819 0.035 Uiso 1 1 calc R . .
C8 C 0.1090(4) 0.2960(2) 0.3256(4) 0.0284(10) Uani 1 1 d . . .
H5 H 0.0930 0.3404 0.3286 0.034 Uiso 1 1 calc R . .
C9 C 0.5675(4) 0.30713(19) 0.1718(3) 0.0219(9) Uani 1 1 d . . .
C10 C 0.6798(4) 0.2701(2) 0.1476(3) 0.0245(9) Uani 1 1 d . . .
H6 H 0.6780 0.2254 0.1585 0.029 Uiso 1 1 calc R . .
C11 C 0.7934(4) 0.2984(2) 0.1080(4) 0.0292(10) Uani 1 1 d . . .
H7 H 0.8688 0.2729 0.0925 0.035 Uiso 1 1 calc R . .
C12 C 0.7974(5) 0.3628(2) 0.0911(4) 0.0319(10) Uani 1 1 d . . .
H8 H 0.8754 0.3819 0.0642 0.038 Uiso 1 1 calc R . .
C13 C 0.6875(5) 0.3996(2) 0.1135(4) 0.0313(10) Uani 1 1 d . . .
H9 H 0.6898 0.4441 0.1007 0.038 Uiso 1 1 calc R . .
C14 C 0.5736(4) 0.3727(2) 0.1544(3) 0.0257(9) Uani 1 1 d . . .
H10 H 0.4996 0.3989 0.1707 0.031 Uiso 1 1 calc R . .
C15 C 0.5303(4) 0.15756(19) 0.3307(3) 0.0199(8) Uani 1 1 d . . .
C16 C 0.5242(4) 0.0927(2) 0.3469(4) 0.0243(9) Uani 1 1 d . . .
H11 H 0.4622 0.0674 0.3011 0.029 Uiso 1 1 calc R . .
C17 C 0.6096(4) 0.0648(2) 0.4305(4) 0.0294(10) Uani 1 1 d . . .
H12 H 0.6054 0.0202 0.4423 0.035 Uiso 1 1 calc R . .
C18 C 0.7005(5) 0.1011(2) 0.4969(4) 0.0365(12) Uani 1 1 d . . .
H13 H 0.7582 0.0816 0.5544 0.044 Uiso 1 1 calc R . .
C19 C 0.7074(5) 0.1658(2) 0.4793(4) 0.0362(11) Uani 1 1 d . . .
H14 H 0.7710 0.1907 0.5242 0.043 Uiso 1 1 calc R . .
C20 C 0.6225(4) 0.1947(2) 0.3971(3) 0.0274(10) Uani 1 1 d . . .
H15 H 0.6267 0.2393 0.3857 0.033 Uiso 1 1 calc R . .
C21 C 0.3917(4) 0.15078(18) 0.1030(3) 0.0185(8) Uani 1 1 d . . .
C22 C 0.2664(4) 0.15211(19) 0.0399(3) 0.0213(8) Uani 1 1 d . . .
H16 H 0.1933 0.1763 0.0643 0.026 Uiso 1 1 calc R . .
C23 C 0.2500(5) 0.1178(2) -0.0587(3) 0.0273(10) Uani 1 1 d . . .
H17 H 0.1653 0.1186 -0.1025 0.033 Uiso 1 1 calc R . .
C24 C 0.3563(5) 0.0825(2) -0.0938(4) 0.0282(10) Uani 1 1 d . . .
H18 H 0.3446 0.0594 -0.1619 0.034 Uiso 1 1 calc R . .
C25 C 0.4801(5) 0.0806(2) -0.0301(4) 0.0267(10) Uani 1 1 d . . .
H19 H 0.5523 0.0558 -0.0542 0.032 Uiso 1 1 calc R . .
C26 C 0.4988(4) 0.11478(19) 0.0683(3) 0.0231(9) Uani 1 1 d . . .
H20 H 0.5837 0.1137 0.1118 0.028 Uiso 1 1 calc R . .
I1 I 0.73314(3) 0.511928(13) 0.71558(2) 0.02615(9) Uani 1 1 d . . .
C27 C 0.4059(5) 0.4361(2) 0.5867(4) 0.0315(10) Uani 1 1 d . . .
H21 H 0.3611 0.4659 0.5314 0.038 Uiso 1 1 calc R . .
H22 H 0.5029 0.4482 0.5989 0.038 Uiso 1 1 calc R . .
Cl1 Cl 0.32927(11) 0.44242(6) 0.71428(9) 0.0329(3) Uani 1 1 d . . .
Cl2 Cl 0.39277(11) 0.35782(5) 0.53357(10) 0.0342(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C15 1.791(4) . ?
P1 C21 1.792(4) . ?
P1 C4 1.795(4) . ?
P1 C1 1.815(4) . ?
C1 C2 1.339(6) . ?
C1 C9 1.474(6) . ?
C2 C3 1.477(6) . ?
C2 H1 0.9500 . ?
C3 C8 1.379(6) . ?
C3 C4 1.398(6) . ?
C4 C5 1.377(6) . ?
C5 C6 1.405(6) . ?
C5 H2 0.9500 . ?
C6 C7 1.376(6) . ?
C6 H3 0.9500 . ?
C7 C8 1.394(6) . ?
C7 H4 0.9500 . ?
C8 H5 0.9500 . ?
C9 C14 1.398(6) . ?
C9 C10 1.407(6) . ?
C10 C11 1.391(6) . ?
C10 H6 0.9500 . ?
C11 C12 1.372(6) . ?
C11 H7 0.9500 . ?
C12 C13 1.380(6) . ?
C12 H8 0.9500 . ?
C13 C14 1.387(6) . ?
C13 H9 0.9500 . ?
C14 H10 0.9500 . ?
C15 C16 1.382(6) . ?
C15 C20 1.398(6) . ?
C16 C17 1.386(6) . ?
C16 H11 0.9500 . ?
C17 C18 1.381(7) . ?
C17 H12 0.9500 . ?
C18 C19 1.381(7) . ?
C18 H13 0.9500 . ?
C19 C20 1.381(6) . ?
C19 H14 0.9500 . ?
C20 H15 0.9500 . ?
C21 C26 1.395(5) . ?
C21 C22 1.396(5) . ?
C22 C23 1.385(6) . ?
C22 H16 0.9500 . ?
C23 C24 1.382(6) . ?
C23 H17 0.9500 . ?
C24 C25 1.388(6) . ?
C24 H18 0.9500 . ?
C25 C26 1.382(6) . ?
C25 H19 0.9500 . ?
C26 H20 0.9500 . ?
C27 Cl2 1.768(5) . ?
C27 Cl1 1.771(4) . ?
C27 H21 0.9900 . ?
C27 H22 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 P1 C21 111.14(18) . . ?
C15 P1 C4 112.33(18) . . ?
C21 P1 C4 110.41(18) . . ?
C15 P1 C1 111.76(19) . . ?
C21 P1 C1 115.62(18) . . ?
C4 P1 C1 94.61(19) . . ?
C2 C1 C9 126.2(4) . . ?
C2 C1 P1 107.2(3) . . ?
C9 C1 P1 126.6(3) . . ?
C1 C2 C3 117.1(4) . . ?
C1 C2 H1 121.5 . . ?
C3 C2 H1 121.5 . . ?
C8 C3 C4 119.6(4) . . ?
C8 C3 C2 126.5(4) . . ?
C4 C3 C2 113.8(4) . . ?
C5 C4 C3 122.3(4) . . ?
C5 C4 P1 130.4(3) . . ?
C3 C4 P1 107.3(3) . . ?
C4 C5 C6 117.3(4) . . ?
C4 C5 H2 121.3 . . ?
C6 C5 H2 121.3 . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 H3 119.6 . . ?
C5 C6 H3 119.6 . . ?
C6 C7 C8 121.1(4) . . ?
C6 C7 H4 119.5 . . ?
C8 C7 H4 119.5 . . ?
C3 C8 C7 118.8(4) . . ?
C3 C8 H5 120.6 . . ?
C7 C8 H5 120.6 . . ?
C14 C9 C10 118.1(4) . . ?
C14 C9 C1 119.8(4) . . ?
C10 C9 C1 122.0(4) . . ?
C11 C10 C9 120.5(4) . . ?
C11 C10 H6 119.8 . . ?
C9 C10 H6 119.8 . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H7 119.7 . . ?
C10 C11 H7 119.7 . . ?
C11 C12 C13 119.5(4) . . ?
C11 C12 H8 120.2 . . ?
C13 C12 H8 120.2 . . ?
C12 C13 C14 121.1(4) . . ?
C12 C13 H9 119.5 . . ?
C14 C13 H9 119.5 . . ?
C13 C14 C9 120.2(4) . . ?
C13 C14 H10 119.9 . . ?
C9 C14 H10 119.9 . . ?
C16 C15 C20 120.4(4) . . ?
C16 C15 P1 119.7(3) . . ?
C20 C15 P1 119.7(3) . . ?
C15 C16 C17 119.3(4) . . ?
C15 C16 H11 120.4 . . ?
C17 C16 H11 120.4 . . ?
C18 C17 C16 120.7(4) . . ?
C18 C17 H12 119.6 . . ?
C16 C17 H12 119.6 . . ?
C17 C18 C19 119.7(4) . . ?
C17 C18 H13 120.1 . . ?
C19 C18 H13 120.1 . . ?
C18 C19 C20 120.6(4) . . ?
C18 C19 H14 119.7 . . ?
C20 C19 H14 119.7 . . ?
C19 C20 C15 119.2(4) . . ?
C19 C20 H15 120.4 . . ?
C15 C20 H15 120.4 . . ?
C26 C21 C22 120.6(4) . . ?
C26 C21 P1 120.7(3) . . ?
C22 C21 P1 118.7(3) . . ?
C23 C22 C21 119.2(4) . . ?
C23 C22 H16 120.4 . . ?
C21 C22 H16 120.4 . . ?
C24 C23 C22 120.3(4) . . ?
C24 C23 H17 119.8 . . ?
C22 C23 H17 119.8 . . ?
C23 C24 C25 120.3(4) . . ?
C23 C24 H18 119.8 . . ?
C25 C24 H18 119.8 . . ?
C26 C25 C24 120.3(4) . . ?
C26 C25 H19 119.8 . . ?
C24 C25 H19 119.8 . . ?
C25 C26 C21 119.2(4) . . ?
C25 C26 H20 120.4 . . ?
C21 C26 H20 120.4 . . ?
Cl2 C27 Cl1 111.0(2) . . ?
Cl2 C27 H21 109.4 . . ?
Cl1 C27 H21 109.4 . . ?
Cl2 C27 H22 109.4 . . ?
Cl1 C27 H22 109.4 . . ?
H21 C27 H22 108.0 . . ?

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 C1 C2 -114.8(3) . . . . ?
C21 P1 C1 C2 116.7(3) . . . . ?
C4 P1 C1 C2 1.5(3) . . . . ?
C15 P1 C1 C9 65.6(4) . . . . ?
C21 P1 C1 C9 -62.9(4) . . . . ?
C4 P1 C1 C9 -178.1(3) . . . . ?
C9 C1 C2 C3 177.4(4) . . . . ?
P1 C1 C2 C3 -2.2(5) . . . . ?
C1 C2 C3 C8 -176.5(4) . . . . ?
C1 C2 C3 C4 2.0(6) . . . . ?
C8 C3 C4 C5 -0.7(6) . . . . ?
C2 C3 C4 C5 -179.4(4) . . . . ?
C8 C3 C4 P1 178.0(3) . . . . ?
C2 C3 C4 P1 -0.7(4) . . . . ?
C15 P1 C4 C5 -66.0(4) . . . . ?
C21 P1 C4 C5 58.7(4) . . . . ?
C1 P1 C4 C5 178.2(4) . . . . ?
C15 P1 C4 C3 115.4(3) . . . . ?
C21 P1 C4 C3 -119.9(3) . . . . ?
C1 P1 C4 C3 -0.4(3) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
P1 C4 C5 C6 -178.6(3) . . . . ?
C4 C5 C6 C7 0.8(6) . . . . ?
C5 C6 C7 C8 -0.5(7) . . . . ?
C4 C3 C8 C7 1.1(6) . . . . ?
C2 C3 C8 C7 179.6(4) . . . . ?
C6 C7 C8 C3 -0.5(7) . . . . ?
C2 C1 C9 C14 -6.6(6) . . . . ?
P1 C1 C9 C14 172.9(3) . . . . ?
C2 C1 C9 C10 172.1(4) . . . . ?
P1 C1 C9 C10 -8.4(6) . . . . ?
C14 C9 C10 C11 0.2(6) . . . . ?
C1 C9 C10 C11 -178.5(4) . . . . ?
C9 C10 C11 C12 -0.4(6) . . . . ?
C10 C11 C12 C13 -0.1(7) . . . . ?
C11 C12 C13 C14 1.0(7) . . . . ?
C12 C13 C14 C9 -1.2(7) . . . . ?
C10 C9 C14 C13 0.6(6) . . . . ?
C1 C9 C14 C13 179.3(4) . . . . ?
C21 P1 C15 C16 -44.8(4) . . . . ?
C4 P1 C15 C16 79.5(4) . . . . ?
C1 P1 C15 C16 -175.6(3) . . . . ?
C21 P1 C15 C20 139.7(3) . . . . ?
C4 P1 C15 C20 -96.1(3) . . . . ?
C1 P1 C15 C20 8.8(4) . . . . ?
C20 C15 C16 C17 0.8(6) . . . . ?
P1 C15 C16 C17 -174.8(3) . . . . ?
C15 C16 C17 C18 -0.4(6) . . . . ?
C16 C17 C18 C19 -0.5(7) . . . . ?
C17 C18 C19 C20 1.0(7) . . . . ?
C18 C19 C20 C15 -0.7(7) . . . . ?
C16 C15 C20 C19 -0.2(6) . . . . ?
P1 C15 C20 C19 175.4(3) . . . . ?
C15 P1 C21 C26 -29.8(4) . . . . ?
C4 P1 C21 C26 -155.1(3) . . . . ?
C1 P1 C21 C26 99.0(3) . . . . ?
C15 P1 C21 C22 149.1(3) . . . . ?
C4 P1 C21 C22 23.7(4) . . . . ?
C1 P1 C21 C22 -82.1(3) . . . . ?
C26 C21 C22 C23 -0.8(6) . . . . ?
P1 C21 C22 C23 -179.6(3) . . . . ?
C21 C22 C23 C24 0.3(6) . . . . ?
C22 C23 C24 C25 0.6(6) . . . . ?
C23 C24 C25 C26 -0.9(6) . . . . ?
C24 C25 C26 C21 0.4(6) . . . . ?
C22 C21 C26 C25 0.5(6) . . . . ?
P1 C21 C26 C25 179.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.766
_refine_diff_density_rms         0.104
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane-diethyl ether'
####################################################################### 
# 
# 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_prpf6
_database_code_depnum_ccdc_archive 'CCDC 1545878'
_audit_update_record             
;
2017-04-25 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        YK_PR_PF6
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 O P, F6 P'
_chemical_formula_sum            'C22 H20 F6 O P2'
_chemical_formula_weight         476.32

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

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

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0781(4)
_cell_length_b                   10.6021(5)
_cell_length_c                   11.4141(4)
_cell_angle_alpha                76.150(3)
_cell_angle_beta                 87.971(3)
_cell_angle_gamma                86.907(3)
_cell_volume                     1064.79(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    17292
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      26.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9120
_exptl_absorpt_correction_T_max  0.9815
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 Blessing, R. H., Acta Cryst., A51, 33-38 (1995).
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            17292
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4068
_reflns_number_gt                4005
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    SIR-2014
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)'
_computing_publication_material  
;Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)
;

_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)+(0.0362P)²+0.9007P] 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         4068
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0923
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
P1 P 0.41932(4) 0.79673(4) 0.74418(3) 0.01657(11) Uani 1 1 d . . .
C1 C 0.40180(17) 0.79904(15) 0.58650(14) 0.0185(3) Uani 1 1 d . . .
C2 C 0.49098(18) 0.70223(16) 0.56198(14) 0.0203(3) Uani 1 1 d . . .
H1 H 0.5002 0.6873 0.4832 0.024 Uiso 1 1 calc R . .
C3 C 0.57305(17) 0.62111(15) 0.66355(14) 0.0195(3) Uani 1 1 d . . .
C4 C 0.54366(17) 0.65630(15) 0.77326(14) 0.0185(3) Uani 1 1 d . . .
C5 C 0.60389(17) 0.58548(16) 0.87997(15) 0.0204(3) Uani 1 1 d . . .
H2 H 0.5830 0.6101 0.9538 0.025 Uiso 1 1 calc R . .
C6 C 0.69619(18) 0.47674(16) 0.87630(15) 0.0231(3) Uani 1 1 d . . .
H3 H 0.7367 0.4253 0.9488 0.028 Uiso 1 1 calc R . .
C7 C 0.72926(19) 0.44315(17) 0.76783(16) 0.0254(4) Uani 1 1 d . . .
H4 H 0.7940 0.3700 0.7667 0.030 Uiso 1 1 calc R . .
C8 C 0.66862(19) 0.51544(17) 0.66033(16) 0.0240(3) Uani 1 1 d . . .
H5 H 0.6925 0.4926 0.5861 0.029 Uiso 1 1 calc R . .
C9 C 0.29751(17) 0.88541(16) 0.50488(14) 0.0198(3) Uani 1 1 d . . .
C10 C 0.22991(19) 0.83978(17) 0.41546(16) 0.0251(4) Uani 1 1 d . . .
H6 H 0.2511 0.7531 0.4084 0.030 Uiso 1 1 calc R . .
C11 C 0.1323(2) 0.92043(18) 0.33726(16) 0.0286(4) Uani 1 1 d . . .
H7 H 0.0868 0.8887 0.2770 0.034 Uiso 1 1 calc R . .
C12 C 0.10094(19) 1.04683(18) 0.34643(16) 0.0267(4) Uani 1 1 d . . .
H8 H 0.0346 1.1019 0.2922 0.032 Uiso 1 1 calc R . .
C13 C 0.16640(19) 1.09303(17) 0.43486(15) 0.0250(4) Uani 1 1 d . . .
H9 H 0.1449 1.1799 0.4412 0.030 Uiso 1 1 calc R . .
C14 C 0.26333(18) 1.01257(16) 0.51413(14) 0.0218(3) Uani 1 1 d . . .
H10 H 0.3068 1.0444 0.5752 0.026 Uiso 1 1 calc R . .
C15 C 0.24395(17) 0.76779(15) 0.81973(14) 0.0181(3) Uani 1 1 d . . .
C16 C 0.16822(18) 0.66501(16) 0.79791(15) 0.0213(3) Uani 1 1 d . . .
H11 H 0.2078 0.6176 0.7423 0.026 Uiso 1 1 calc R . .
C17 C 0.03515(19) 0.63238(16) 0.85768(16) 0.0244(4) Uani 1 1 d . . .
H12 H -0.0168 0.5624 0.8431 0.029 Uiso 1 1 calc R . .
C18 C -0.02230(18) 0.70217(17) 0.93903(15) 0.0239(3) Uani 1 1 d . . .
H13 H -0.1128 0.6788 0.9809 0.029 Uiso 1 1 calc R . .
C19 C 0.05155(18) 0.80553(17) 0.95931(15) 0.0234(3) Uani 1 1 d . . .
H14 H 0.0108 0.8535 1.0141 0.028 Uiso 1 1 calc R . .
C20 C 0.18546(18) 0.83965(16) 0.89972(15) 0.0212(3) Uani 1 1 d . . .
H15 H 0.2362 0.9107 0.9133 0.025 Uiso 1 1 calc R . .
C21 C 0.50274(18) 0.93937(16) 0.76818(15) 0.0212(3) Uani 1 1 d . . .
H16 H 0.5666 0.9761 0.6975 0.025 Uiso 1 1 calc R . .
H17 H 0.4242 1.0059 0.7750 0.025 Uiso 1 1 calc R . .
C22 C 0.59445(19) 0.90879(17) 0.88163(16) 0.0254(4) Uani 1 1 d . . .
H18 H 0.6825 0.8527 0.8715 0.030 Uiso 1 1 calc R . .
H19 H 0.6276 0.9900 0.8985 0.030 Uiso 1 1 calc R . .
O1 O 0.50210(14) 0.84341(13) 0.97749(11) 0.0286(3) Uani 1 1 d . . .
H20 H 0.5526 0.8141 1.0392 0.043 Uiso 1 1 calc R . .
P2 P 0.26453(5) 0.30359(4) 0.74738(4) 0.02239(12) Uani 1 1 d . . .
F1 F 0.23466(14) 0.17192(11) 0.84920(11) 0.0420(3) Uani 1 1 d . . .
F2 F 0.29909(13) 0.43369(10) 0.64917(9) 0.0324(3) Uani 1 1 d . . .
F3 F 0.09822(12) 0.35408(11) 0.76148(10) 0.0350(3) Uani 1 1 d . . .
F4 F 0.43295(12) 0.25085(11) 0.73653(11) 0.0347(3) Uani 1 1 d . . .
F5 F 0.22091(14) 0.23584(13) 0.64484(12) 0.0453(3) Uani 1 1 d . . .
F6 F 0.31130(13) 0.36955(11) 0.85242(9) 0.0332(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C15 1.7892(16) . ?
P1 C4 1.7915(16) . ?
P1 C1 1.8066(16) . ?
P1 C21 1.8088(16) . ?
C1 C2 1.349(2) . ?
C1 C9 1.471(2) . ?
C2 C3 1.467(2) . ?
C2 H1 0.9500 . ?
C3 C8 1.386(2) . ?
C3 C4 1.403(2) . ?
C4 C5 1.382(2) . ?
C5 C6 1.396(2) . ?
C5 H2 0.9500 . ?
C6 C7 1.387(2) . ?
C6 H3 0.9500 . ?
C7 C8 1.396(2) . ?
C7 H4 0.9500 . ?
C8 H5 0.9500 . ?
C9 C14 1.395(2) . ?
C9 C10 1.402(2) . ?
C10 C11 1.386(2) . ?
C10 H6 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H7 0.9500 . ?
C12 C13 1.386(3) . ?
C12 H8 0.9500 . ?
C13 C14 1.388(2) . ?
C13 H9 0.9500 . ?
C14 H10 0.9500 . ?
C15 C16 1.395(2) . ?
C15 C20 1.397(2) . ?
C16 C17 1.385(2) . ?
C16 H11 0.9500 . ?
C17 C18 1.391(2) . ?
C17 H12 0.9500 . ?
C18 C19 1.384(3) . ?
C18 H13 0.9500 . ?
C19 C20 1.394(2) . ?
C19 H14 0.9500 . ?
C20 H15 0.9500 . ?
C21 C22 1.524(2) . ?
C21 H16 0.9900 . ?
C21 H17 0.9900 . ?
C22 O1 1.420(2) . ?
C22 H18 0.9900 . ?
C22 H19 0.9900 . ?
O1 H20 0.8400 . ?
P2 F5 1.5839(12) . ?
P2 F3 1.5902(11) . ?
P2 F2 1.5935(11) . ?
P2 F6 1.6051(11) . ?
P2 F4 1.6104(11) . ?
P2 F1 1.6170(12) . ?

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 C4 113.16(7) . . ?
C15 P1 C1 109.37(7) . . ?
C4 P1 C1 94.07(7) . . ?
C15 P1 C21 113.22(8) . . ?
C4 P1 C21 112.35(8) . . ?
C1 P1 C21 113.21(7) . . ?
C2 C1 C9 127.33(15) . . ?
C2 C1 P1 107.93(12) . . ?
C9 C1 P1 124.53(12) . . ?
C1 C2 C3 116.44(14) . . ?
C1 C2 H1 121.8 . . ?
C3 C2 H1 121.8 . . ?
C8 C3 C4 119.66(15) . . ?
C8 C3 C2 126.61(15) . . ?
C4 C3 C2 113.70(14) . . ?
C5 C4 C3 121.65(15) . . ?
C5 C4 P1 130.58(13) . . ?
C3 C4 P1 107.76(12) . . ?
C4 C5 C6 118.18(15) . . ?
C4 C5 H2 120.9 . . ?
C6 C5 H2 120.9 . . ?
C7 C6 C5 120.66(15) . . ?
C7 C6 H3 119.7 . . ?
C5 C6 H3 119.7 . . ?
C6 C7 C8 120.85(16) . . ?
C6 C7 H4 119.6 . . ?
C8 C7 H4 119.6 . . ?
C3 C8 C7 118.95(16) . . ?
C3 C8 H5 120.5 . . ?
C7 C8 H5 120.5 . . ?
C14 C9 C10 118.69(15) . . ?
C14 C9 C1 121.60(15) . . ?
C10 C9 C1 119.71(15) . . ?
C11 C10 C9 120.34(16) . . ?
C11 C10 H6 119.8 . . ?
C9 C10 H6 119.8 . . ?
C12 C11 C10 120.36(17) . . ?
C12 C11 H7 119.8 . . ?
C10 C11 H7 119.8 . . ?
C11 C12 C13 119.92(16) . . ?
C11 C12 H8 120.0 . . ?
C13 C12 H8 120.0 . . ?
C12 C13 C14 120.09(16) . . ?
C12 C13 H9 120.0 . . ?
C14 C13 H9 120.0 . . ?
C13 C14 C9 120.60(16) . . ?
C13 C14 H10 119.7 . . ?
C9 C14 H10 119.7 . . ?
C16 C15 C20 120.57(15) . . ?
C16 C15 P1 116.30(12) . . ?
C20 C15 P1 123.10(12) . . ?
C17 C16 C15 119.74(15) . . ?
C17 C16 H11 120.1 . . ?
C15 C16 H11 120.1 . . ?
C16 C17 C18 119.91(16) . . ?
C16 C17 H12 120.0 . . ?
C18 C17 H12 120.0 . . ?
C19 C18 C17 120.41(15) . . ?
C19 C18 H13 119.8 . . ?
C17 C18 H13 119.8 . . ?
C18 C19 C20 120.34(15) . . ?
C18 C19 H14 119.8 . . ?
C20 C19 H14 119.8 . . ?
C19 C20 C15 119.01(15) . . ?
C19 C20 H15 120.5 . . ?
C15 C20 H15 120.5 . . ?
C22 C21 P1 112.17(12) . . ?
C22 C21 H16 109.2 . . ?
P1 C21 H16 109.2 . . ?
C22 C21 H17 109.2 . . ?
P1 C21 H17 109.2 . . ?
H16 C21 H17 107.9 . . ?
O1 C22 C21 106.69(13) . . ?
O1 C22 H18 110.4 . . ?
C21 C22 H18 110.4 . . ?
O1 C22 H19 110.4 . . ?
C21 C22 H19 110.4 . . ?
H18 C22 H19 108.6 . . ?
C22 O1 H20 109.5 . . ?
F5 P2 F3 91.03(7) . . ?
F5 P2 F2 90.81(7) . . ?
F3 P2 F2 91.08(6) . . ?
F5 P2 F6 178.71(7) . . ?
F3 P2 F6 89.99(6) . . ?
F2 P2 F6 89.95(6) . . ?
F5 P2 F4 89.77(7) . . ?
F3 P2 F4 178.62(7) . . ?
F2 P2 F4 90.03(6) . . ?
F6 P2 F4 89.19(6) . . ?
F5 P2 F1 90.53(7) . . ?
F3 P2 F1 90.30(6) . . ?
F2 P2 F1 178.06(7) . . ?
F6 P2 F1 88.68(7) . . ?
F4 P2 F1 88.57(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 P1 C1 C2 -118.85(12) . . . . ?
C4 P1 C1 C2 -2.55(12) . . . . ?
C21 P1 C1 C2 113.88(12) . . . . ?
C15 P1 C1 C9 56.27(15) . . . . ?
C4 P1 C1 C9 172.57(14) . . . . ?
C21 P1 C1 C9 -71.00(15) . . . . ?
C9 C1 C2 C3 -173.55(15) . . . . ?
P1 C1 C2 C3 1.39(18) . . . . ?
C1 C2 C3 C8 178.83(16) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C8 C3 C4 C5 -2.2(2) . . . . ?
C2 C3 C4 C5 175.83(14) . . . . ?
C8 C3 C4 P1 179.17(13) . . . . ?
C2 C3 C4 P1 -2.80(17) . . . . ?
C15 P1 C4 C5 -62.33(17) . . . . ?
C1 P1 C4 C5 -175.41(16) . . . . ?
C21 P1 C4 C5 67.43(17) . . . . ?
C15 P1 C4 C3 116.13(12) . . . . ?
C1 P1 C4 C3 3.05(12) . . . . ?
C21 P1 C4 C3 -114.11(12) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
P1 C4 C5 C6 178.40(12) . . . . ?
C4 C5 C6 C7 1.7(2) . . . . ?
C5 C6 C7 C8 -1.4(3) . . . . ?
C4 C3 C8 C7 2.4(2) . . . . ?
C2 C3 C8 C7 -175.31(16) . . . . ?
C6 C7 C8 C3 -0.7(3) . . . . ?
C2 C1 C9 C14 -149.76(17) . . . . ?
P1 C1 C9 C14 36.1(2) . . . . ?
C2 C1 C9 C10 30.4(2) . . . . ?
P1 C1 C9 C10 -143.78(14) . . . . ?
C14 C9 C10 C11 0.7(2) . . . . ?
C1 C9 C10 C11 -179.46(16) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C9 0.9(3) . . . . ?
C10 C9 C14 C13 -1.2(2) . . . . ?
C1 C9 C14 C13 178.96(15) . . . . ?
C4 P1 C15 C16 -55.31(14) . . . . ?
C1 P1 C15 C16 48.11(14) . . . . ?
C21 P1 C15 C16 175.38(12) . . . . ?
C4 P1 C15 C20 122.61(14) . . . . ?
C1 P1 C15 C20 -133.97(13) . . . . ?
C21 P1 C15 C20 -6.70(16) . . . . ?
C20 C15 C16 C17 -1.2(2) . . . . ?
P1 C15 C16 C17 176.81(13) . . . . ?
C15 C16 C17 C18 0.0(2) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
C18 C19 C20 C15 -0.2(2) . . . . ?
C16 C15 C20 C19 1.2(2) . . . . ?
P1 C15 C20 C19 -176.59(12) . . . . ?
C15 P1 C21 C22 87.51(13) . . . . ?
C4 P1 C21 C22 -42.22(14) . . . . ?
C1 P1 C21 C22 -147.27(11) . . . . ?
P1 C21 C22 O1 -52.50(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.048
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane--toluene'
####################################################################### 
# 
# 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_pmepf6
_database_code_depnum_ccdc_archive 'CCDC 1545874'
_audit_update_record             
;
2017-04-25 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 P1, P1 F6'
_chemical_formula_sum            'C21 H18 F6 P2'
_chemical_formula_weight         446.29

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'

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

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                   11.5651(2)
_cell_length_b                   8.32080(10)
_cell_length_c                   20.4281(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.8115(9)
_cell_angle_gamma                90.00
_cell_volume                     1958.89(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    32989
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      26.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9696
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 Blessing, R. H., Acta Cryst., A51, 33-38 (1995).
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            32989
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3843
_reflns_number_gt                3724
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    SIR-2014
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)'
_computing_publication_material  
;Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)
;

_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)+(0.0400P)²+1.9701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3843
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1001
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
P1 P 0.68917(4) 0.00444(6) 0.63245(2) 0.02566(14) Uani 1 1 d . . .
C1 C 0.83801(17) 0.0681(2) 0.63226(9) 0.0283(4) Uani 1 1 d . . .
C5 C 0.7875(2) -0.4331(3) 0.51905(11) 0.0372(5) Uani 1 1 d . . .
H5 H 0.814(2) -0.517(3) 0.4957(13) 0.045(7) Uiso 1 1 d . . .
C11 C 1.01612(19) 0.4453(3) 0.65283(12) 0.0392(5) Uani 1 1 d . . .
H11 H 1.080(2) 0.494(3) 0.6356(13) 0.048(7) Uiso 1 1 d . . .
C12 C 0.9616(2) 0.5261(3) 0.70041(11) 0.0410(5) Uani 1 1 d . . .
H12 H 0.992(2) 0.631(4) 0.7144(13) 0.054(8) Uiso 1 1 d . . .
C13 C 0.8675(2) 0.4585(3) 0.72646(11) 0.0408(5) Uani 1 1 d . . .
H13 H 0.830(2) 0.513(3) 0.7592(14) 0.053(8) Uiso 1 1 d . . .
C14 C 0.8261(2) 0.3093(3) 0.70476(11) 0.0352(5) Uani 1 1 d . . .
H14 H 0.763(2) 0.266(3) 0.7236(12) 0.039(6) Uiso 1 1 d . . .
C18 C 0.6888(2) -0.1511(3) 0.81985(11) 0.0365(5) Uani 1 1 d . . .
C19 C 0.5944(2) -0.0724(3) 0.84185(10) 0.0362(5) Uani 1 1 d . . .
H19 H 0.579(2) -0.082(3) 0.8866(13) 0.043(7) Uiso 1 1 d . . .
C20 C 0.5246(2) 0.0239(3) 0.80039(11) 0.0374(5) Uani 1 1 d . . .
H20 H 0.458(2) 0.076(3) 0.8143(12) 0.045(7) Uiso 1 1 d . . .
P2 P 0.74089(4) 0.12563(6) 0.41002(2) 0.02590(14) Uani 1 1 d . . .
F3 F 0.67210(13) -0.00255(17) 0.45051(7) 0.0491(4) Uani 1 1 d . . .
F2 F 0.82904(13) 0.15355(18) 0.47320(7) 0.0547(4) Uani 1 1 d . . .
F1 F 0.65178(13) 0.09743(18) 0.34788(7) 0.0535(4) Uani 1 1 d . . .
F5 F 0.66023(12) 0.26644(16) 0.43485(7) 0.0452(3) Uani 1 1 d . . .
C2 C 0.89574(18) -0.0462(3) 0.60132(10) 0.0306(4) Uani 1 1 d . . .
H2 H 0.978(2) -0.035(3) 0.5943(10) 0.028(5) Uiso 1 1 d . . .
C6 C 0.6710(2) -0.4238(3) 0.53174(10) 0.0347(5) Uani 1 1 d . . .
H6 H 0.618(2) -0.503(3) 0.5159(12) 0.036(6) Uiso 1 1 d . . .
C15 C 0.59291(19) 0.1440(3) 0.58938(10) 0.0299(4) Uani 1 1 d . . .
C16 C 0.64705(16) -0.0294(2) 0.71382(9) 0.0261(4) Uani 1 1 d . . .
C17 C 0.71620(19) -0.1296(3) 0.75564(10) 0.0330(4) Uani 1 1 d . . .
H17 H 0.783(2) -0.184(3) 0.7399(12) 0.044(7) Uiso 1 1 d . . .
C21 C 0.55039(18) 0.0466(3) 0.73590(10) 0.0314(4) Uani 1 1 d . . .
H21 H 0.501(2) 0.116(3) 0.7066(12) 0.043(7) Uiso 1 1 d . . .
F4 F 0.80895(13) 0.25321(17) 0.37066(7) 0.0530(4) Uani 1 1 d . . .
F6 F 0.82111(11) -0.01564(16) 0.38657(7) 0.0442(3) Uani 1 1 d . . .
C4 C 0.86595(19) -0.3131(3) 0.54079(10) 0.0344(5) Uani 1 1 d . . .
H4 H 0.948(2) -0.321(3) 0.5323(11) 0.034(6) Uiso 1 1 d . . .
C8 C 0.70947(18) -0.1776(2) 0.58825(9) 0.0280(4) Uani 1 1 d . . .
C7 C 0.63075(19) -0.2942(3) 0.56662(10) 0.0306(4) Uani 1 1 d . . .
H7 H 0.550(2) -0.286(3) 0.5754(11) 0.036(6) Uiso 1 1 d . . .
C9 C 0.88044(17) 0.2257(2) 0.65651(9) 0.0292(4) Uani 1 1 d . . .
C3 C 0.82641(17) -0.1848(2) 0.57592(9) 0.0292(4) Uani 1 1 d . . .
C10 C 0.97688(18) 0.2961(3) 0.63069(11) 0.0340(5) Uani 1 1 d . . .
H10 H 1.012(2) 0.239(3) 0.5951(13) 0.048(7) Uiso 1 1 d . . .
H22 H 0.598(2) 0.244(3) 0.6127(12) 0.041(7) Uiso 1 1 d . . .
H1 H 0.735(2) -0.219(3) 0.8487(13) 0.046(7) Uiso 1 1 d . . .
H23 H 0.516(2) 0.101(3) 0.5862(11) 0.037(6) Uiso 1 1 d . . .
H24 H 0.620(2) 0.157(3) 0.5455(13) 0.045(7) Uiso 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 1.788(2) . ?
P1 C8 1.789(2) . ?
P1 C16 1.7930(19) . ?
P1 C1 1.801(2) . ?
C1 C2 1.349(3) . ?
C1 C9 1.472(3) . ?
C5 C6 1.395(3) . ?
C5 C4 1.396(3) . ?
C5 H5 0.91(3) . ?
C11 C12 1.378(4) . ?
C11 C10 1.384(3) . ?
C11 H11 0.94(3) . ?
C12 C13 1.371(4) . ?
C12 H12 0.97(3) . ?
C13 C14 1.390(3) . ?
C13 H13 0.94(3) . ?
C14 C9 1.397(3) . ?
C14 H14 0.92(2) . ?
C18 C19 1.380(3) . ?
C18 C17 1.387(3) . ?
C18 H1 0.95(3) . ?
C19 C20 1.377(3) . ?
C19 H19 0.95(3) . ?
C20 C21 1.388(3) . ?
C20 H20 0.95(3) . ?
P2 F4 1.5808(13) . ?
P2 F1 1.5841(14) . ?
P2 F2 1.5933(14) . ?
P2 F6 1.5958(13) . ?
P2 F3 1.6015(13) . ?
P2 F5 1.6061(13) . ?
C2 C3 1.474(3) . ?
C2 H2 0.98(2) . ?
C6 C7 1.394(3) . ?
C6 H6 0.94(3) . ?
C15 H22 0.96(3) . ?
C15 H23 0.96(2) . ?
C15 H24 0.98(3) . ?
C16 C21 1.392(3) . ?
C16 C17 1.397(3) . ?
C17 H17 0.97(3) . ?
C21 H21 0.98(3) . ?
C4 C3 1.385(3) . ?
C4 H4 0.98(2) . ?
C8 C7 1.378(3) . ?
C8 C3 1.398(3) . ?
C7 H7 0.97(2) . ?
C9 C10 1.401(3) . ?
C10 H10 0.99(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 P1 C8 113.84(10) . . ?
C15 P1 C16 110.60(10) . . ?
C8 P1 C16 113.09(9) . . ?
C15 P1 C1 111.33(10) . . ?
C8 P1 C1 94.69(9) . . ?
C16 P1 C1 112.47(9) . . ?
C2 C1 C9 128.44(19) . . ?
C2 C1 P1 107.74(15) . . ?
C9 C1 P1 123.56(15) . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 120.5(17) . . ?
C4 C5 H5 118.6(17) . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 118.4(16) . . ?
C10 C11 H11 120.9(16) . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 122.0(16) . . ?
C11 C12 H12 118.1(17) . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13 120.4(17) . . ?
C14 C13 H13 119.2(17) . . ?
C13 C14 C9 120.4(2) . . ?
C13 C14 H14 118.4(15) . . ?
C9 C14 H14 121.2(16) . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H1 120.2(16) . . ?
C17 C18 H1 120.0(16) . . ?
C20 C19 C18 121.0(2) . . ?
C20 C19 H19 119.4(15) . . ?
C18 C19 H19 119.6(15) . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20 122.1(16) . . ?
C21 C20 H20 117.8(16) . . ?
F4 P2 F1 90.58(9) . . ?
F4 P2 F2 90.11(9) . . ?
F1 P2 F2 179.17(9) . . ?
F4 P2 F6 90.87(8) . . ?
F1 P2 F6 90.34(8) . . ?
F2 P2 F6 90.11(8) . . ?
F4 P2 F3 179.45(9) . . ?
F1 P2 F3 89.84(9) . . ?
F2 P2 F3 89.46(9) . . ?
F6 P2 F3 89.48(8) . . ?
F4 P2 F5 89.88(8) . . ?
F1 P2 F5 90.29(8) . . ?
F2 P2 F5 89.25(8) . . ?
F6 P2 F5 179.02(8) . . ?
F3 P2 F5 89.76(7) . . ?
C1 C2 C3 116.13(18) . . ?
C1 C2 H2 121.8(13) . . ?
C3 C2 H2 122.0(13) . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 118.9(15) . . ?
C5 C6 H6 120.6(15) . . ?
P1 C15 H22 108.2(15) . . ?
P1 C15 H23 109.2(15) . . ?
H22 C15 H23 112(2) . . ?
P1 C15 H24 106.7(15) . . ?
H22 C15 H24 111(2) . . ?
H23 C15 H24 110(2) . . ?
C21 C16 C17 120.49(18) . . ?
C21 C16 P1 121.13(15) . . ?
C17 C16 P1 118.34(15) . . ?
C18 C17 C16 119.4(2) . . ?
C18 C17 H17 120.3(15) . . ?
C16 C17 H17 120.3(15) . . ?
C20 C21 C16 119.2(2) . . ?
C20 C21 H21 120.2(15) . . ?
C16 C21 H21 120.6(15) . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 H4 120.7(14) . . ?
C5 C4 H4 120.4(14) . . ?
C7 C8 C3 122.38(19) . . ?
C7 C8 P1 130.31(16) . . ?
C3 C8 P1 107.29(15) . . ?
C8 C7 C6 117.9(2) . . ?
C8 C7 H7 120.8(15) . . ?
C6 C7 H7 121.3(15) . . ?
C14 C9 C10 118.48(19) . . ?
C14 C9 C1 121.58(19) . . ?
C10 C9 C1 119.94(19) . . ?
C4 C3 C8 119.54(19) . . ?
C4 C3 C2 126.30(19) . . ?
C8 C3 C2 114.14(18) . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 122.1(16) . . ?
C9 C10 H10 117.7(16) . . ?

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 C1 C2 -118.87(15) . . . . ?
C8 P1 C1 C2 -1.00(16) . . . . ?
C16 P1 C1 C2 116.37(15) . . . . ?
C15 P1 C1 C9 55.64(18) . . . . ?
C8 P1 C1 C9 173.50(16) . . . . ?
C16 P1 C1 C9 -69.13(18) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C9 0.6(3) . . . . ?
C17 C18 C19 C20 1.9(3) . . . . ?
C18 C19 C20 C21 -1.7(3) . . . . ?
C9 C1 C2 C3 -173.20(18) . . . . ?
P1 C1 C2 C3 1.0(2) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C15 P1 C16 C21 0.7(2) . . . . ?
C8 P1 C16 C21 -128.34(17) . . . . ?
C1 P1 C16 C21 125.84(17) . . . . ?
C15 P1 C16 C17 -176.97(16) . . . . ?
C8 P1 C16 C17 54.01(19) . . . . ?
C1 P1 C16 C17 -51.80(19) . . . . ?
C19 C18 C17 C16 -0.5(3) . . . . ?
C21 C16 C17 C18 -1.0(3) . . . . ?
P1 C16 C17 C18 176.70(16) . . . . ?
C19 C20 C21 C16 0.2(3) . . . . ?
C17 C16 C21 C20 1.1(3) . . . . ?
P1 C16 C21 C20 -176.47(16) . . . . ?
C6 C5 C4 C3 0.7(3) . . . . ?
C15 P1 C8 C7 -61.8(2) . . . . ?
C16 P1 C8 C7 65.5(2) . . . . ?
C1 P1 C8 C7 -177.62(19) . . . . ?
C15 P1 C8 C3 116.60(15) . . . . ?
C16 P1 C8 C3 -116.07(14) . . . . ?
C1 P1 C8 C3 0.79(15) . . . . ?
C3 C8 C7 C6 0.5(3) . . . . ?
P1 C8 C7 C6 178.74(16) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C13 C14 C9 C10 -0.2(3) . . . . ?
C13 C14 C9 C1 -179.6(2) . . . . ?
C2 C1 C9 C14 -159.5(2) . . . . ?
P1 C1 C9 C14 27.2(3) . . . . ?
C2 C1 C9 C10 21.1(3) . . . . ?
P1 C1 C9 C10 -152.18(17) . . . . ?
C5 C4 C3 C8 -0.6(3) . . . . ?
C5 C4 C3 C2 -178.5(2) . . . . ?
C7 C8 C3 C4 0.0(3) . . . . ?
P1 C8 C3 C4 -178.60(16) . . . . ?
C7 C8 C3 C2 178.16(18) . . . . ?
P1 C8 C3 C2 -0.4(2) . . . . ?
C1 C2 C3 C4 177.7(2) . . . . ?
C1 C2 C3 C8 -0.4(3) . . . . ?
C12 C11 C10 C9 0.2(3) . . . . ?
C14 C9 C10 C11 -0.2(3) . . . . ?
C1 C9 C10 C11 179.22(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.896
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.045
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane-diethyl ether'
####################################################################### 
# 
# 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_phppf6
_database_code_depnum_ccdc_archive 'CCDC 1545876'
_audit_update_record             
;
2017-04-25 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        YK_PPh_PF6
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 P, F6 P '
_chemical_formula_sum            'C26 H20 F6 P2'
_chemical_formula_weight         508.36

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

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

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                   9.1887(2)
_cell_length_b                   19.4913(3)
_cell_length_c                   13.1164(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.3225(14)
_cell_angle_gamma                90.00
_cell_volume                     2303.42(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    35987
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9355
_exptl_absorpt_correction_T_max  0.9634
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 Blessing, R. H., Acta Cryst., A51, 33-38 (1995).
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            35987
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4396
_reflns_number_gt                4326
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    SIR-2014
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)'
_computing_publication_material  
;Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)
;

_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)+(0.0361P)²+2.0543P] 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         4396
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0963
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.21806(4) 0.22666(2) 0.60659(3) 0.01964(12) Uani 1 1 d . . .
C1 C 0.36476(17) 0.25299(8) 0.71248(12) 0.0217(3) Uani 1 1 d . . .
C2 C 0.38907(19) 0.32053(9) 0.69943(13) 0.0249(3) Uani 1 1 d . . .
H1 H 0.4660 0.3446 0.7442 0.030 Uiso 1 1 calc R . .
C3 C 0.29090(19) 0.35472(9) 0.61273(13) 0.0242(3) Uani 1 1 d . . .
C4 C 0.18871(18) 0.31094(8) 0.55172(13) 0.0233(3) Uani 1 1 d . . .
C5 C 0.0835(2) 0.33445(9) 0.46937(13) 0.0273(4) Uani 1 1 d . . .
H2 H 0.0149 0.3038 0.4290 0.033 Uiso 1 1 calc R . .
C6 C 0.0808(2) 0.40443(10) 0.44700(14) 0.0307(4) Uani 1 1 d . . .
H3 H 0.0099 0.4219 0.3903 0.037 Uiso 1 1 calc R . .
C7 C 0.1809(2) 0.44884(9) 0.50694(15) 0.0310(4) Uani 1 1 d . . .
H4 H 0.1769 0.4964 0.4910 0.037 Uiso 1 1 calc R . .
C8 C 0.2870(2) 0.42471(9) 0.59011(14) 0.0290(4) Uani 1 1 d . . .
H5 H 0.3554 0.4554 0.6306 0.035 Uiso 1 1 calc R . .
C9 C 0.44070(17) 0.20818(9) 0.79674(12) 0.0223(3) Uani 1 1 d . . .
C10 C 0.55247(19) 0.23463(9) 0.87581(13) 0.0266(4) Uani 1 1 d . . .
H6 H 0.5795 0.2816 0.8747 0.032 Uiso 1 1 calc R . .
C11 C 0.6233(2) 0.19253(10) 0.95526(14) 0.0323(4) Uani 1 1 d . . .
H7 H 0.6986 0.2109 1.0083 0.039 Uiso 1 1 calc R . .
C12 C 0.5851(2) 0.12374(10) 0.95801(14) 0.0329(4) Uani 1 1 d . . .
H8 H 0.6343 0.0950 1.0126 0.039 Uiso 1 1 calc R . .
C13 C 0.4753(2) 0.09730(9) 0.88095(14) 0.0300(4) Uani 1 1 d . . .
H9 H 0.4489 0.0502 0.8827 0.036 Uiso 1 1 calc R . .
C14 C 0.40314(18) 0.13892(9) 0.80108(13) 0.0251(3) Uani 1 1 d . . .
H10 H 0.3274 0.1201 0.7487 0.030 Uiso 1 1 calc R . .
C15 C 0.05249(17) 0.19746(8) 0.64602(12) 0.0212(3) Uani 1 1 d . . .
C16 C -0.02879(18) 0.24599(9) 0.69044(13) 0.0239(3) Uani 1 1 d . . .
H11 H 0.0024 0.2925 0.6966 0.029 Uiso 1 1 calc R . .
C17 C -0.15491(19) 0.22560(9) 0.72527(13) 0.0269(4) Uani 1 1 d . . .
H12 H -0.2106 0.2582 0.7555 0.032 Uiso 1 1 calc R . .
C18 C -0.20001(18) 0.15737(10) 0.71589(13) 0.0276(4) Uani 1 1 d . . .
H13 H -0.2857 0.1433 0.7408 0.033 Uiso 1 1 calc R . .
C19 C -0.12049(19) 0.10974(9) 0.67037(14) 0.0279(4) Uani 1 1 d . . .
H14 H -0.1531 0.0634 0.6632 0.033 Uiso 1 1 calc R . .
C20 C 0.00665(18) 0.12923(8) 0.63512(13) 0.0243(3) Uani 1 1 d . . .
H15 H 0.0613 0.0966 0.6041 0.029 Uiso 1 1 calc R . .
C21 C 0.28191(18) 0.16524(8) 0.52396(13) 0.0217(3) Uani 1 1 d . . .
C22 C 0.18292(19) 0.13910(9) 0.43834(14) 0.0258(4) Uani 1 1 d . . .
H16 H 0.0825 0.1540 0.4236 0.031 Uiso 1 1 calc R . .
C23 C 0.2330(2) 0.09110(9) 0.37497(14) 0.0285(4) Uani 1 1 d . . .
H17 H 0.1670 0.0732 0.3161 0.034 Uiso 1 1 calc R . .
C24 C 0.37952(19) 0.06922(9) 0.39758(13) 0.0261(4) Uani 1 1 d . . .
H18 H 0.4124 0.0356 0.3548 0.031 Uiso 1 1 calc R . .
C25 C 0.47830(19) 0.09580(9) 0.48167(13) 0.0258(4) Uani 1 1 d . . .
H19 H 0.5787 0.0809 0.4959 0.031 Uiso 1 1 calc R . .
C26 C 0.43021(18) 0.14426(9) 0.54499(13) 0.0243(3) Uani 1 1 d . . .
H20 H 0.4977 0.1631 0.6024 0.029 Uiso 1 1 calc R . .
P2 P 0.21336(5) -0.05461(2) 0.70475(3) 0.02237(12) Uani 1 1 d . . .
F1 F 0.35058(13) -0.07179(7) 0.79694(10) 0.0469(3) Uani 1 1 d . . .
F2 F 0.07853(13) -0.03680(6) 0.61264(9) 0.0370(3) Uani 1 1 d . . .
F3 F 0.31867(12) -0.00599(6) 0.65257(9) 0.0387(3) Uani 1 1 d . . .
F4 F 0.10775(13) -0.10321(6) 0.75679(10) 0.0407(3) Uani 1 1 d . . .
F5 F 0.17166(12) 0.00904(5) 0.76996(8) 0.0333(3) Uani 1 1 d . . .
F6 F 0.25622(15) -0.11911(6) 0.64075(10) 0.0441(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C21 1.7894(16) . ?
P1 C4 1.7925(17) . ?
P1 C15 1.7931(16) . ?
P1 C1 1.8094(16) . ?
C1 C2 1.352(2) . ?
C1 C9 1.473(2) . ?
C2 C3 1.466(2) . ?
C2 H1 0.9500 . ?
C3 C8 1.395(2) . ?
C3 C4 1.398(2) . ?
C4 C5 1.379(2) . ?
C5 C6 1.394(3) . ?
C5 H2 0.9500 . ?
C6 C7 1.389(3) . ?
C6 H3 0.9500 . ?
C7 C8 1.395(3) . ?
C7 H4 0.9500 . ?
C8 H5 0.9500 . ?
C9 C14 1.397(2) . ?
C9 C10 1.406(2) . ?
C10 C11 1.384(3) . ?
C10 H6 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H7 0.9500 . ?
C12 C13 1.381(3) . ?
C12 H8 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H9 0.9500 . ?
C14 H10 0.9500 . ?
C15 C20 1.394(2) . ?
C15 C16 1.401(2) . ?
C16 C17 1.385(2) . ?
C16 H11 0.9500 . ?
C17 C18 1.391(3) . ?
C17 H12 0.9500 . ?
C18 C19 1.387(3) . ?
C18 H13 0.9500 . ?
C19 C20 1.391(2) . ?
C19 H14 0.9500 . ?
C20 H15 0.9500 . ?
C21 C22 1.395(2) . ?
C21 C26 1.397(2) . ?
C22 C23 1.389(2) . ?
C22 H16 0.9500 . ?
C23 C24 1.387(2) . ?
C23 H17 0.9500 . ?
C24 C25 1.384(2) . ?
C24 H18 0.9500 . ?
C25 C26 1.386(2) . ?
C25 H19 0.9500 . ?
C26 H20 0.9500 . ?
P2 F2 1.5898(11) . ?
P2 F5 1.5957(10) . ?
P2 F3 1.6008(11) . ?
P2 F1 1.6016(12) . ?
P2 F4 1.6017(11) . ?
P2 F6 1.6032(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
C21 P1 C4 114.29(8) . . ?
C21 P1 C15 111.10(8) . . ?
C4 P1 C15 109.72(8) . . ?
C21 P1 C1 111.79(8) . . ?
C4 P1 C1 94.53(8) . . ?
C15 P1 C1 114.52(7) . . ?
C2 C1 C9 127.37(15) . . ?
C2 C1 P1 107.20(12) . . ?
C9 C1 P1 125.43(12) . . ?
C1 C2 C3 116.69(15) . . ?
C1 C2 H1 121.7 . . ?
C3 C2 H1 121.7 . . ?
C8 C3 C4 119.27(16) . . ?
C8 C3 C2 126.56(16) . . ?
C4 C3 C2 114.11(15) . . ?
C5 C4 C3 122.29(16) . . ?
C5 C4 P1 130.26(14) . . ?
C3 C4 P1 107.35(12) . . ?
C4 C5 C6 118.10(17) . . ?
C4 C5 H2 120.9 . . ?
C6 C5 H2 120.9 . . ?
C7 C6 C5 120.52(17) . . ?
C7 C6 H3 119.7 . . ?
C5 C6 H3 119.7 . . ?
C6 C7 C8 121.09(16) . . ?
C6 C7 H4 119.5 . . ?
C8 C7 H4 119.5 . . ?
C7 C8 C3 118.73(17) . . ?
C7 C8 H5 120.6 . . ?
C3 C8 H5 120.6 . . ?
C14 C9 C10 118.33(15) . . ?
C14 C9 C1 121.27(15) . . ?
C10 C9 C1 120.39(15) . . ?
C11 C10 C9 120.33(16) . . ?
C11 C10 H6 119.8 . . ?
C9 C10 H6 119.8 . . ?
C10 C11 C12 120.56(17) . . ?
C10 C11 H7 119.7 . . ?
C12 C11 H7 119.7 . . ?
C13 C12 C11 119.58(17) . . ?
C13 C12 H8 120.2 . . ?
C11 C12 H8 120.2 . . ?
C12 C13 C14 120.47(17) . . ?
C12 C13 H9 119.8 . . ?
C14 C13 H9 119.8 . . ?
C13 C14 C9 120.72(16) . . ?
C13 C14 H10 119.6 . . ?
C9 C14 H10 119.6 . . ?
C20 C15 C16 120.79(15) . . ?
C20 C15 P1 121.99(13) . . ?
C16 C15 P1 117.22(12) . . ?
C17 C16 C15 119.50(16) . . ?
C17 C16 H11 120.3 . . ?
C15 C16 H11 120.3 . . ?
C16 C17 C18 119.95(16) . . ?
C16 C17 H12 120.0 . . ?
C18 C17 H12 120.0 . . ?
C19 C18 C17 120.33(16) . . ?
C19 C18 H13 119.8 . . ?
C17 C18 H13 119.8 . . ?
C18 C19 C20 120.53(16) . . ?
C18 C19 H14 119.7 . . ?
C20 C19 H14 119.7 . . ?
C19 C20 C15 118.89(16) . . ?
C19 C20 H15 120.6 . . ?
C15 C20 H15 120.6 . . ?
C22 C21 C26 120.56(15) . . ?
C22 C21 P1 119.50(12) . . ?
C26 C21 P1 119.94(13) . . ?
C23 C22 C21 119.16(16) . . ?
C23 C22 H16 120.4 . . ?
C21 C22 H16 120.4 . . ?
C24 C23 C22 120.07(16) . . ?
C24 C23 H17 120.0 . . ?
C22 C23 H17 120.0 . . ?
C25 C24 C23 120.80(16) . . ?
C25 C24 H18 119.6 . . ?
C23 C24 H18 119.6 . . ?
C24 C25 C26 119.75(16) . . ?
C24 C25 H19 120.1 . . ?
C26 C25 H19 120.1 . . ?
C25 C26 C21 119.63(16) . . ?
C25 C26 H20 120.2 . . ?
C21 C26 H20 120.2 . . ?
F2 P2 F5 90.25(6) . . ?
F2 P2 F3 89.55(6) . . ?
F5 P2 F3 89.88(6) . . ?
F2 P2 F1 179.21(7) . . ?
F5 P2 F1 89.67(6) . . ?
F3 P2 F1 89.67(7) . . ?
F2 P2 F4 90.34(6) . . ?
F5 P2 F4 90.12(6) . . ?
F3 P2 F4 179.89(8) . . ?
F1 P2 F4 90.44(7) . . ?
F2 P2 F6 90.47(7) . . ?
F5 P2 F6 179.19(7) . . ?
F3 P2 F6 90.52(6) . . ?
F1 P2 F6 89.62(7) . . ?
F4 P2 F6 89.48(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 P1 C1 C2 115.59(12) . . . . ?
C4 P1 C1 C2 -2.84(13) . . . . ?
C15 P1 C1 C2 -116.93(12) . . . . ?
C21 P1 C1 C9 -64.91(15) . . . . ?
C4 P1 C1 C9 176.66(14) . . . . ?
C15 P1 C1 C9 62.57(16) . . . . ?
C9 C1 C2 C3 -175.79(15) . . . . ?
P1 C1 C2 C3 3.70(18) . . . . ?
C1 C2 C3 C8 174.05(17) . . . . ?
C1 C2 C3 C4 -3.0(2) . . . . ?
C8 C3 C4 C5 0.1(3) . . . . ?
C2 C3 C4 C5 177.32(15) . . . . ?
C8 C3 C4 P1 -176.72(13) . . . . ?
C2 C3 C4 P1 0.53(17) . . . . ?
C21 P1 C4 C5 68.46(18) . . . . ?
C15 P1 C4 C5 -57.08(18) . . . . ?
C1 P1 C4 C5 -175.16(16) . . . . ?
C21 P1 C4 C3 -115.10(12) . . . . ?
C15 P1 C4 C3 119.36(12) . . . . ?
C1 P1 C4 C3 1.28(12) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
P1 C4 C5 C6 176.16(13) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C8 0.5(3) . . . . ?
C6 C7 C8 C3 -0.3(3) . . . . ?
C4 C3 C8 C7 0.0(3) . . . . ?
C2 C3 C8 C7 -176.90(16) . . . . ?
C2 C1 C9 C14 179.42(16) . . . . ?
P1 C1 C9 C14 0.0(2) . . . . ?
C2 C1 C9 C10 0.1(3) . . . . ?
P1 C1 C9 C10 -179.30(12) . . . . ?
C14 C9 C10 C11 0.3(2) . . . . ?
C1 C9 C10 C11 179.69(15) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C9 0.3(3) . . . . ?
C10 C9 C14 C13 -0.5(2) . . . . ?
C1 C9 C14 C13 -179.86(15) . . . . ?
C21 P1 C15 C20 15.44(16) . . . . ?
C4 P1 C15 C20 142.78(14) . . . . ?
C1 P1 C15 C20 -112.40(15) . . . . ?
C21 P1 C15 C16 -165.68(12) . . . . ?
C4 P1 C15 C16 -38.34(15) . . . . ?
C1 P1 C15 C16 66.48(15) . . . . ?
C20 C15 C16 C17 1.0(2) . . . . ?
P1 C15 C16 C17 -177.93(13) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 -1.0(3) . . . . ?
C17 C18 C19 C20 1.1(3) . . . . ?
C18 C19 C20 C15 -0.2(3) . . . . ?
C16 C15 C20 C19 -0.8(2) . . . . ?
P1 C15 C20 C19 178.01(13) . . . . ?
C4 P1 C21 C22 -74.34(15) . . . . ?
C15 P1 C21 C22 50.47(15) . . . . ?
C1 P1 C21 C22 179.77(13) . . . . ?
C4 P1 C21 C26 105.12(14) . . . . ?
C15 P1 C21 C26 -130.06(13) . . . . ?
C1 P1 C21 C26 -0.77(16) . . . . ?
C26 C21 C22 C23 1.0(3) . . . . ?
P1 C21 C22 C23 -179.57(13) . . . . ?
C21 C22 C23 C24 0.6(3) . . . . ?
C22 C23 C24 C25 -1.5(3) . . . . ?
C23 C24 C25 C26 0.8(3) . . . . ?
C24 C25 C26 C21 0.7(2) . . . . ?
C22 C21 C26 C25 -1.6(2) . . . . ?
P1 C21 C26 C25 178.91(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.893
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.044
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform-toluene'
####################################################################### 
# 
# 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_pri
_database_code_depnum_ccdc_archive 'CCDC 1545877'
_audit_update_record             
;
2017-04-25 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        YK_PR_I
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 O P, I'
_chemical_formula_sum            'C22 H20 I O P'
_chemical_formula_weight         458.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_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                   9.41250(10)
_cell_length_b                   22.5530(4)
_cell_length_c                   10.2457(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.7384(11)
_cell_angle_gamma                90.00
_cell_volume                     1942.39(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    108(2)
_cell_measurement_reflns_used    50099
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      26.5

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    1.738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5432
_exptl_absorpt_correction_T_max  0.8454
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 Blessing, R. H., Acta Cryst., A51, 33-38 (1995).
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      108(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            50099
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0115
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         26.50
_reflns_number_total             4015
_reflns_number_gt                3800
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    SHELXT-2013
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)'
_computing_publication_material  
;Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)
;

_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)+(0.0174P)²+1.3441P] 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         4015
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0168
_refine_ls_wR_factor_ref         0.0430
_refine_ls_wR_factor_gt          0.0417
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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
I1 I 0.771845(13) 0.135785(5) 0.595901(11) 0.02421(4) Uani 1 1 d . . .
P1 P 0.95975(5) 0.115729(17) 0.13819(4) 0.01660(8) Uani 1 1 d . . .
C1 C 0.90688(18) 0.03907(7) 0.14670(17) 0.0184(3) Uani 1 1 d . . .
C2 C 1.00008(19) 0.01897(7) 0.28271(18) 0.0207(3) Uani 1 1 d . . .
H1 H 0.9904 -0.0202 0.3116 0.025 Uiso 1 1 calc R . .
C3 C 1.11728(19) 0.06079(7) 0.38390(18) 0.0210(3) Uani 1 1 d . . .
C4 C 1.11090(18) 0.11734(7) 0.32303(18) 0.0200(3) Uani 1 1 d . . .
C5 C 1.21680(18) 0.16193(8) 0.40011(18) 0.0231(3) Uani 1 1 d . . .
H2 H 1.2125 0.1996 0.3570 0.028 Uiso 1 1 calc R . .
C6 C 1.3297(2) 0.14987(8) 0.5425(2) 0.0276(4) Uani 1 1 d . . .
H3 H 1.4026 0.1799 0.5982 0.033 Uiso 1 1 calc R . .
C7 C 1.3370(2) 0.09445(9) 0.60407(19) 0.0287(4) Uani 1 1 d . . .
H4 H 1.4150 0.0871 0.7014 0.034 Uiso 1 1 calc R . .
C8 C 1.2317(2) 0.04943(8) 0.52554(19) 0.0262(4) Uani 1 1 d . . .
H5 H 1.2382 0.0115 0.5684 0.031 Uiso 1 1 calc R . .
C9 C 0.77808(18) 0.00695(7) 0.02709(18) 0.0192(3) Uani 1 1 d . . .
C10 C 0.69469(19) -0.03773(7) 0.05934(18) 0.0214(3) Uani 1 1 d . . .
H6 H 0.7181 -0.0454 0.1581 0.026 Uiso 1 1 calc R . .
C11 C 0.5788(2) -0.07062(7) -0.0515(2) 0.0248(3) Uani 1 1 d . . .
H7 H 0.5231 -0.1006 -0.0282 0.030 Uiso 1 1 calc R . .
C12 C 0.5432(2) -0.06013(8) -0.1963(2) 0.0266(4) Uani 1 1 d . . .
H8 H 0.4650 -0.0833 -0.2718 0.032 Uiso 1 1 calc R . .
C13 C 0.6225(2) -0.01558(8) -0.23007(19) 0.0255(3) Uani 1 1 d . . .
H9 H 0.5976 -0.0080 -0.3292 0.031 Uiso 1 1 calc R . .
C14 C 0.73847(19) 0.01809(7) -0.11961(18) 0.0219(3) Uani 1 1 d . . .
H10 H 0.7911 0.0489 -0.1440 0.026 Uiso 1 1 calc R . .
C15 C 0.79141(17) 0.16184(7) 0.10344(17) 0.0178(3) Uani 1 1 d . . .
C16 C 0.75964(19) 0.17656(7) 0.21991(18) 0.0206(3) Uani 1 1 d . . .
H11 H 0.8278 0.1631 0.3158 0.025 Uiso 1 1 calc R . .
C17 C 0.6274(2) 0.21110(7) 0.19440(19) 0.0241(3) Uani 1 1 d . . .
H12 H 0.6059 0.2219 0.2734 0.029 Uiso 1 1 calc R . .
C18 C 0.52662(19) 0.22978(7) 0.0535(2) 0.0246(3) Uani 1 1 d . . .
H13 H 0.4374 0.2540 0.0367 0.030 Uiso 1 1 calc R . .
C19 C 0.5556(2) 0.21328(7) -0.06302(19) 0.0240(3) Uani 1 1 d . . .
H14 H 0.4843 0.2251 -0.1595 0.029 Uiso 1 1 calc R . .
C20 C 0.68885(19) 0.17945(7) -0.03869(18) 0.0214(3) Uani 1 1 d . . .
H15 H 0.7097 0.1685 -0.1179 0.026 Uiso 1 1 calc R . .
C21 C 1.03975(19) 0.12866(7) 0.01075(18) 0.0201(3) Uani 1 1 d . . .
H16 H 1.1004 0.0932 0.0080 0.024 Uiso 1 1 calc R . .
H17 H 0.9507 0.1341 -0.0881 0.024 Uiso 1 1 calc R . .
C22 C 1.1484(2) 0.18275(7) 0.0488(2) 0.0259(4) Uani 1 1 d . . .
H18 H 1.2494 0.1747 0.1370 0.031 Uiso 1 1 calc R . .
H19 H 1.1734 0.1922 -0.0330 0.031 Uiso 1 1 calc R . .
O1 O 1.06757(16) 0.23106(5) 0.07485(17) 0.0341(3) Uani 1 1 d . . .
H20 H 1.1181 0.2626 0.0818 0.051 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 C4 1.7854(17) . ?
P1 C15 1.7919(15) . ?
P1 C21 1.8004(16) . ?
P1 C1 1.8119(16) . ?
C1 C2 1.348(2) . ?
C1 C9 1.470(2) . ?
C2 C3 1.467(2) . ?
C2 H1 0.9500 . ?
C3 C8 1.388(2) . ?
C3 C4 1.409(2) . ?
C4 C5 1.386(2) . ?
C5 C6 1.392(2) . ?
C5 H2 0.9500 . ?
C6 C7 1.388(3) . ?
C6 H3 0.9500 . ?
C7 C8 1.394(3) . ?
C7 H4 0.9500 . ?
C8 H5 0.9500 . ?
C9 C14 1.399(2) . ?
C9 C10 1.405(2) . ?
C10 C11 1.384(2) . ?
C10 H6 0.9500 . ?
C11 C12 1.386(3) . ?
C11 H7 0.9500 . ?
C12 C13 1.385(2) . ?
C12 H8 0.9500 . ?
C13 C14 1.392(2) . ?
C13 H9 0.9500 . ?
C14 H10 0.9500 . ?
C15 C16 1.395(2) . ?
C15 C20 1.395(2) . ?
C16 C17 1.390(2) . ?
C16 H11 0.9500 . ?
C17 C18 1.389(2) . ?
C17 H12 0.9500 . ?
C18 C19 1.390(2) . ?
C18 H13 0.9500 . ?
C19 C20 1.391(2) . ?
C19 H14 0.9500 . ?
C20 H15 0.9500 . ?
C21 C22 1.526(2) . ?
C21 H16 0.9900 . ?
C21 H17 0.9900 . ?
C22 O1 1.422(2) . ?
C22 H18 0.9900 . ?
C22 H19 0.9900 . ?
O1 H20 0.8400 . ?

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
C4 P1 C15 114.22(7) . . ?
C4 P1 C21 111.86(8) . . ?
C15 P1 C21 112.51(7) . . ?
C4 P1 C1 94.21(8) . . ?
C15 P1 C1 109.01(7) . . ?
C21 P1 C1 113.76(7) . . ?
C2 C1 C9 127.25(14) . . ?
C2 C1 P1 107.79(12) . . ?
C9 C1 P1 124.87(12) . . ?
C1 C2 C3 116.56(14) . . ?
C1 C2 H1 121.7 . . ?
C3 C2 H1 121.7 . . ?
C8 C3 C4 119.24(15) . . ?
C8 C3 C2 127.12(15) . . ?
C4 C3 C2 113.60(14) . . ?
C5 C4 C3 121.88(15) . . ?
C5 C4 P1 130.16(13) . . ?
C3 C4 P1 107.81(12) . . ?
C4 C5 C6 118.03(16) . . ?
C4 C5 H2 121.0 . . ?
C6 C5 H2 121.0 . . ?
C7 C6 C5 120.69(17) . . ?
C7 C6 H3 119.7 . . ?
C5 C6 H3 119.7 . . ?
C6 C7 C8 121.13(16) . . ?
C6 C7 H4 119.4 . . ?
C8 C7 H4 119.4 . . ?
C3 C8 C7 119.02(16) . . ?
C3 C8 H5 120.5 . . ?
C7 C8 H5 120.5 . . ?
C14 C9 C10 118.33(15) . . ?
C14 C9 C1 121.90(14) . . ?
C10 C9 C1 119.74(14) . . ?
C11 C10 C9 120.60(15) . . ?
C11 C10 H6 119.7 . . ?
C9 C10 H6 119.7 . . ?
C10 C11 C12 120.54(16) . . ?
C10 C11 H7 119.7 . . ?
C12 C11 H7 119.7 . . ?
C13 C12 C11 119.57(16) . . ?
C13 C12 H8 120.2 . . ?
C11 C12 H8 120.2 . . ?
C12 C13 C14 120.40(16) . . ?
C12 C13 H9 119.8 . . ?
C14 C13 H9 119.8 . . ?
C13 C14 C9 120.53(15) . . ?
C13 C14 H10 119.7 . . ?
C9 C14 H10 119.7 . . ?
C16 C15 C20 120.76(14) . . ?
C16 C15 P1 118.62(12) . . ?
C20 C15 P1 120.50(12) . . ?
C17 C16 C15 119.42(15) . . ?
C17 C16 H11 120.3 . . ?
C15 C16 H11 120.3 . . ?
C18 C17 C16 120.04(15) . . ?
C18 C17 H12 120.0 . . ?
C16 C17 H12 120.0 . . ?
C17 C18 C19 120.35(15) . . ?
C17 C18 H13 119.8 . . ?
C19 C18 H13 119.8 . . ?
C18 C19 C20 120.17(16) . . ?
C18 C19 H14 119.9 . . ?
C20 C19 H14 119.9 . . ?
C19 C20 C15 119.21(15) . . ?
C19 C20 H15 120.4 . . ?
C15 C20 H15 120.4 . . ?
C22 C21 P1 113.29(12) . . ?
C22 C21 H16 108.9 . . ?
P1 C21 H16 108.9 . . ?
C22 C21 H17 108.9 . . ?
P1 C21 H17 108.9 . . ?
H16 C21 H17 107.7 . . ?
O1 C22 C21 107.86(13) . . ?
O1 C22 H18 110.1 . . ?
C21 C22 H18 110.1 . . ?
O1 C22 H19 110.1 . . ?
C21 C22 H19 110.1 . . ?
H18 C22 H19 108.4 . . ?
C22 O1 H20 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 P1 C1 C2 0.54(12) . . . . ?
C15 P1 C1 C2 -116.88(12) . . . . ?
C21 P1 C1 C2 116.66(12) . . . . ?
C4 P1 C1 C9 177.26(13) . . . . ?
C15 P1 C1 C9 59.84(14) . . . . ?
C21 P1 C1 C9 -66.62(15) . . . . ?
C9 C1 C2 C3 -177.99(14) . . . . ?
P1 C1 C2 C3 -1.37(17) . . . . ?
C1 C2 C3 C8 -175.91(16) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C8 C3 C4 C5 0.6(2) . . . . ?
C2 C3 C4 C5 -177.26(14) . . . . ?
C8 C3 C4 P1 176.69(13) . . . . ?
C2 C3 C4 P1 -1.21(17) . . . . ?
C15 P1 C4 C5 -70.95(17) . . . . ?
C21 P1 C4 C5 58.31(17) . . . . ?
C1 P1 C4 C5 176.01(16) . . . . ?
C15 P1 C4 C3 113.44(12) . . . . ?
C21 P1 C4 C3 -117.30(11) . . . . ?
C1 P1 C4 C3 0.41(12) . . . . ?
C3 C4 C5 C6 -1.3(2) . . . . ?
P1 C4 C5 C6 -176.33(13) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C4 C3 C8 C7 0.3(2) . . . . ?
C2 C3 C8 C7 177.85(16) . . . . ?
C6 C7 C8 C3 -0.5(3) . . . . ?
C2 C1 C9 C14 -150.16(17) . . . . ?
P1 C1 C9 C14 33.8(2) . . . . ?
C2 C1 C9 C10 27.7(2) . . . . ?
P1 C1 C9 C10 -148.38(13) . . . . ?
C14 C9 C10 C11 1.4(2) . . . . ?
C1 C9 C10 C11 -176.56(14) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C9 0.8(2) . . . . ?
C10 C9 C14 C13 -1.9(2) . . . . ?
C1 C9 C14 C13 176.02(15) . . . . ?
C4 P1 C15 C16 -23.57(15) . . . . ?
C21 P1 C15 C16 -152.50(12) . . . . ?
C1 P1 C15 C16 80.33(14) . . . . ?
C4 P1 C15 C20 160.42(13) . . . . ?
C21 P1 C15 C20 31.49(15) . . . . ?
C1 P1 C15 C20 -95.68(14) . . . . ?
C20 C15 C16 C17 -2.5(2) . . . . ?
P1 C15 C16 C17 -178.47(12) . . . . ?
C15 C16 C17 C18 1.1(2) . . . . ?
C16 C17 C18 C19 1.1(2) . . . . ?
C17 C18 C19 C20 -2.0(2) . . . . ?
C18 C19 C20 C15 0.7(2) . . . . ?
C16 C15 C20 C19 1.5(2) . . . . ?
P1 C15 C20 C19 177.46(12) . . . . ?
C4 P1 C21 C22 -49.19(14) . . . . ?
C15 P1 C21 C22 80.96(13) . . . . ?
C1 P1 C21 C22 -154.44(11) . . . . ?
P1 C21 C22 O1 -49.53(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.052
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane--toluene'
####################################################################### 
# 
# 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_sample1
_database_code_depnum_ccdc_archive 'CCDC 1545873'
_audit_update_record             
;
2017-04-25 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21 H18 I P'
_chemical_formula_moiety         'C21 H18 P +, I -'
_chemical_formula_weight         428.25
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.19717(17)
_cell_length_b                   19.1790(4)
_cell_length_c                   10.65593(19)
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.343(7)
_cell_angle_gamma                90.0000
_cell_volume                     1836.18(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    28287
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    103
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848.00
_exptl_absorpt_coefficient_mu    1.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_T_max  0.896

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      103
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            30889
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.107
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4200
_reflns_number_gt                4016
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0523
_refine_ls_wR_factor_gt          0.0516
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4200
_refine_ls_number_parameters     209
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0210P)²+2.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.003
_refine_diff_density_max         0.63
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
P P 0.1023 0.0942
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.21052(2) 0.66848(2) 0.24868(2) 0.02025(5) Uani 1 4 d . . .
P1 P 0.48274(5) 0.61020(2) 0.70506(4) 0.01111(9) Uani 1 4 d . . .
C1 C 0.4346(2) 0.51853(9) 0.69536(17) 0.0134(3) Uani 1 4 d . . .
C2 C 0.5299(2) 0.48534(10) 0.79057(18) 0.0174(4) Uani 1 4 d . . .
C3 C 0.6428(2) 0.52855(10) 0.87317(18) 0.0169(4) Uani 1 4 d . . .
C4 C 0.7566(2) 0.50607(11) 0.97285(19) 0.0228(4) Uani 1 4 d . . .
C5 C 0.8545(2) 0.55533(12) 1.0402(2) 0.0254(4) Uani 1 4 d . . .
C6 C 0.8411(2) 0.62562(12) 1.0091(2) 0.0245(4) Uani 1 4 d . . .
C7 C 0.7288(2) 0.64863(11) 0.90768(19) 0.0207(4) Uani 1 4 d . . .
C8 C 0.6314(2) 0.59987(10) 0.84199(17) 0.0152(3) Uani 1 4 d . . .
C9 C 0.5485(2) 0.64643(10) 0.57308(17) 0.0149(3) Uani 1 4 d . . .
C10 C 0.3342(2) 0.66287(9) 0.73598(17) 0.0127(3) Uani 1 4 d . . .
C11 C 0.3104(2) 0.66710(11) 0.8609(2) 0.0214(4) Uani 1 4 d . . .
C12 C 0.1923(3) 0.70653(13) 0.8842(2) 0.0300(5) Uani 1 4 d . . .
C13 C 0.0993(2) 0.74120(11) 0.7848(2) 0.0269(4) Uani 1 4 d . . .
C14 C 0.1229(2) 0.73709(11) 0.6613(2) 0.0228(4) Uani 1 4 d . . .
C15 C 0.2402(2) 0.69797(10) 0.63551(19) 0.0172(3) Uani 1 4 d . . .
C16 C 0.30881(19) 0.48761(9) 0.60338(17) 0.0140(3) Uani 1 4 d . . .
C17 C 0.2616(2) 0.51534(9) 0.48036(18) 0.0164(3) Uani 1 4 d . . .
C18 C 0.1465(2) 0.48415(10) 0.3923(2) 0.0202(4) Uani 1 4 d . . .
C19 C 0.0764(2) 0.42535(11) 0.4268(2) 0.0218(4) Uani 1 4 d . . .
C20 C 0.1202(2) 0.39811(10) 0.5496(2) 0.0214(4) Uani 1 4 d . . .
C21 C 0.2354(2) 0.42868(10) 0.63779(19) 0.0179(4) Uani 1 4 d . . .
H2 H 0.524 0.43649 0.8034 0.0208 Uiso 1 4 calc R . .
H4 H 0.76733 0.45804 0.99463 0.0273 Uiso 1 4 calc R . .
H5 H 0.93197 0.54047 1.10892 0.0305 Uiso 1 4 calc R . .
H6 H 0.90867 0.65825 1.05691 0.0294 Uiso 1 4 calc R . .
H7 H 0.71976 0.69654 0.88469 0.0248 Uiso 1 4 calc R . .
H9A H 0.46648 0.64862 0.49745 0.0179 Uiso 1 4 calc R . .
H9B H 0.62826 0.61703 0.55407 0.0179 Uiso 1 4 calc R . .
H9C H 0.58689 0.69351 0.59529 0.0179 Uiso 1 4 calc R . .
H11 H 0.3744 0.64325 0.92923 0.0256 Uiso 1 4 calc R . .
H12 H 0.17544 0.70968 0.96887 0.0360 Uiso 1 4 calc R . .
H13 H 0.01874 0.76803 0.80155 0.0323 Uiso 1 4 calc R . .
H14 H 0.0584 0.76116 0.5936 0.0274 Uiso 1 4 calc R . .
H15 H 0.25631 0.69514 0.55052 0.0206 Uiso 1 4 calc R . .
H17 H 0.30841 0.55591 0.45653 0.0196 Uiso 1 4 calc R . .
H18 H 0.11588 0.50315 0.30851 0.0243 Uiso 1 4 calc R . .
H19 H -0.00147 0.40376 0.36628 0.0262 Uiso 1 4 calc R . .
H20 H 0.07097 0.35829 0.57356 0.0256 Uiso 1 4 calc R . .
H21 H 0.26481 0.40969 0.72174 0.0215 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
P1 C1 1.8106(18) yes . .
P1 C8 1.7844(17) yes . .
P1 C9 1.786(2) yes . .
P1 C10 1.7853(19) yes . .
C1 C2 1.350(2) yes . .
C1 C16 1.472(2) yes . .
C2 C3 1.466(3) yes . .
C3 C4 1.390(3) yes . .
C3 C8 1.406(3) yes . .
C4 C5 1.394(3) yes . .
C5 C6 1.387(3) yes . .
C6 C7 1.397(3) yes . .
C7 C8 1.378(3) yes . .
C10 C11 1.397(3) yes . .
C10 C15 1.397(2) yes . .
C11 C12 1.389(3) yes . .
C12 C13 1.381(3) yes . .
C13 C14 1.381(3) yes . .
C14 C15 1.389(3) yes . .
C16 C17 1.395(3) yes . .
C16 C21 1.405(3) yes . .
C17 C18 1.390(2) yes . .
C18 C19 1.387(3) yes . .
C19 C20 1.387(3) yes . .
C20 C21 1.387(3) yes . .
C2 H2 0.950 no . .
C4 H4 0.950 no . .
C5 H5 0.950 no . .
C6 H6 0.950 no . .
C7 H7 0.950 no . .
C9 H9A 0.980 no . .
C9 H9B 0.980 no . .
C9 H9C 0.980 no . .
C11 H11 0.950 no . .
C12 H12 0.950 no . .
C13 H13 0.950 no . .
C14 H14 0.950 no . .
C15 H15 0.950 no . .
C17 H17 0.950 no . .
C18 H18 0.950 no . .
C19 H19 0.950 no . .
C20 H20 0.950 no . .
C21 H21 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 P1 C8 94.25(8) yes . . .
C1 P1 C9 116.92(9) yes . . .
C1 P1 C10 111.87(9) yes . . .
C8 P1 C9 110.97(9) yes . . .
C8 P1 C10 113.24(9) yes . . .
C9 P1 C10 109.05(9) yes . . .
P1 C1 C2 107.66(13) yes . . .
P1 C1 C16 125.25(12) yes . . .
C2 C1 C16 127.02(16) yes . . .
C1 C2 C3 116.58(17) yes . . .
C2 C3 C4 127.17(18) yes . . .
C2 C3 C8 113.59(15) yes . . .
C4 C3 C8 119.23(17) yes . . .
C3 C4 C5 118.75(19) yes . . .
C4 C5 C6 121.41(18) yes . . .
C5 C6 C7 120.32(19) yes . . .
C6 C7 C8 118.12(19) yes . . .
P1 C8 C3 107.87(13) yes . . .
P1 C8 C7 129.88(15) yes . . .
C3 C8 C7 122.17(16) yes . . .
P1 C10 C11 119.38(14) yes . . .
P1 C10 C15 120.26(15) yes . . .
C11 C10 C15 120.33(18) yes . . .
C10 C11 C12 119.32(18) yes . . .
C11 C12 C13 120.4(2) yes . . .
C12 C13 C14 120.4(2) yes . . .
C13 C14 C15 120.41(18) yes . . .
C10 C15 C14 119.23(19) yes . . .
C1 C16 C17 120.99(16) yes . . .
C1 C16 C21 120.23(16) yes . . .
C17 C16 C21 118.77(15) yes . . .
C16 C17 C18 120.61(17) yes . . .
C17 C18 C19 120.08(18) yes . . .
C18 C19 C20 119.89(18) yes . . .
C19 C20 C21 120.37(19) yes . . .
C16 C21 C20 120.24(18) yes . . .
C1 C2 H2 121.706 no . . .
C3 C2 H2 121.712 no . . .
C3 C4 H4 120.628 no . . .
C5 C4 H4 120.625 no . . .
C4 C5 H5 119.300 no . . .
C6 C5 H5 119.293 no . . .
C5 C6 H6 119.833 no . . .
C7 C6 H6 119.850 no . . .
C6 C7 H7 120.936 no . . .
C8 C7 H7 120.941 no . . .
P1 C9 H9A 109.476 no . . .
P1 C9 H9B 109.470 no . . .
P1 C9 H9C 109.478 no . . .
H9A C9 H9B 109.468 no . . .
H9A C9 H9C 109.473 no . . .
H9B C9 H9C 109.464 no . . .
C10 C11 H11 120.341 no . . .
C12 C11 H11 120.342 no . . .
C11 C12 H12 119.830 no . . .
C13 C12 H12 119.818 no . . .
C12 C13 H13 119.818 no . . .
C14 C13 H13 119.816 no . . .
C13 C14 H14 119.798 no . . .
C15 C14 H14 119.797 no . . .
C10 C15 H15 120.396 no . . .
C14 C15 H15 120.378 no . . .
C16 C17 H17 119.693 no . . .
C18 C17 H17 119.698 no . . .
C17 C18 H18 119.952 no . . .
C19 C18 H18 119.963 no . . .
C18 C19 H19 120.051 no . . .
C20 C19 H19 120.056 no . . .
C19 C20 H20 119.811 no . . .
C21 C20 H20 119.814 no . . .
C16 C21 H21 119.886 no . . .
C20 C21 H21 119.874 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 P1 C8 C3 1.76(13) no . . . .
C1 P1 C8 C7 178.36(17) no . . . .
C8 P1 C1 C2 -0.81(13) no . . . .
C8 P1 C1 C16 176.39(15) no . . . .
C9 P1 C1 C2 115.31(12) no . . . .
C9 P1 C1 C16 -67.49(17) no . . . .
C1 P1 C10 C11 78.72(13) no . . . .
C1 P1 C10 C15 -99.53(13) no . . . .
C10 P1 C1 C2 -117.95(12) no . . . .
C10 P1 C1 C16 59.25(17) no . . . .
C9 P1 C8 C3 -119.21(12) no . . . .
C9 P1 C8 C7 57.39(19) no . . . .
C8 P1 C10 C11 -26.31(16) no . . . .
C8 P1 C10 C15 155.44(12) no . . . .
C10 P1 C8 C3 117.76(12) no . . . .
C10 P1 C8 C7 -65.64(19) no . . . .
C9 P1 C10 C11 -150.38(11) no . . . .
C9 P1 C10 C15 31.37(15) no . . . .
P1 C1 C2 C3 -0.4(2) no . . . .
P1 C1 C16 C17 32.5(3) no . . . .
P1 C1 C16 C21 -148.42(13) no . . . .
C2 C1 C16 C17 -150.84(19) no . . . .
C2 C1 C16 C21 28.2(3) no . . . .
C16 C1 C2 C3 -177.51(17) no . . . .
C1 C2 C3 C4 -176.76(18) no . . . .
C1 C2 C3 C8 1.8(3) no . . . .
C2 C3 C4 C5 179.51(18) no . . . .
C2 C3 C8 P1 -2.3(2) no . . . .
C2 C3 C8 C7 -179.17(16) no . . . .
C4 C3 C8 P1 176.44(17) no . . . .
C4 C3 C8 C7 -0.5(3) no . . . .
C8 C3 C4 C5 1.0(3) no . . . .
C3 C4 C5 C6 -0.5(3) no . . . .
C4 C5 C6 C7 -0.6(3) no . . . .
C5 C6 C7 C8 1.1(3) no . . . .
C6 C7 C8 P1 -176.75(17) no . . . .
C6 C7 C8 C3 -0.6(3) no . . . .
P1 C10 C11 C12 -178.22(12) no . . . .
P1 C10 C15 C14 178.22(11) no . . . .
C11 C10 C15 C14 -0.0(3) no . . . .
C15 C10 C11 C12 0.0(3) no . . . .
C10 C11 C12 C13 0.0(3) no . . . .
C11 C12 C13 C14 -0.1(3) no . . . .
C12 C13 C14 C15 0.1(3) no . . . .
C13 C14 C15 C10 -0.0(3) no . . . .
C1 C16 C17 C18 177.43(15) no . . . .
C1 C16 C21 C20 -177.80(16) no . . . .
C17 C16 C21 C20 1.3(3) no . . . .
C21 C16 C17 C18 -1.7(3) no . . . .
C16 C17 C18 C19 0.7(3) no . . . .
C17 C18 C19 C20 0.7(3) no . . . .
C18 C19 C20 C21 -1.1(3) no . . . .
C19 C20 C21 C16 0.1(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
P1 C17 3.3315(17) no . .
C2 C21 3.046(3) no . .
C3 C6 2.786(3) no . .
C4 C7 2.819(3) no . .
C5 C8 2.747(3) no . .
C7 C9 3.597(3) no . .
C8 C11 3.266(3) no . .
C9 C15 3.204(3) no . .
C10 C13 2.770(3) no . .
C11 C14 2.781(3) no . .
C12 C15 2.782(3) no . .
C16 C19 2.796(2) no . .
C17 C20 2.775(3) no . .
C18 C21 2.780(3) no . .
C9 C16 3.595(3) no . 3_666
C16 C9 3.595(3) no . 3_666
C18 C19 3.553(3) no . 3_566
C18 C20 3.485(3) no . 3_566
C19 C18 3.553(3) no . 3_566
C20 C18 3.485(3) no . 3_566
P1 H2 3.4888 no . .
P1 H7 3.0617 no . .
P1 H11 2.8493 no . .
P1 H15 2.8699 no . .
P1 H17 2.9754 no . .
C1 H9A 3.3201 no . .
C1 H9B 3.1868 no . .
C1 H11 3.5816 no . .
C1 H17 2.6598 no . .
C1 H21 2.6574 no . .
C2 H4 2.7825 no . .
C2 H21 2.7965 no . .
C3 H5 3.2525 no . .
C3 H7 3.2953 no . .
C3 H11 3.4528 no . .
C4 H2 2.8222 no . .
C4 H6 3.2775 no . .
C5 H7 3.2769 no . .
C6 H4 3.2817 no . .
C7 H5 3.2682 no . .
C7 H9C 3.4157 no . .
C7 H11 3.3173 no . .
C8 H2 3.2847 no . .
C8 H4 3.2770 no . .
C8 H6 3.2413 no . .
C8 H9B 3.0797 no . .
C8 H9C 3.1374 no . .
C8 H11 2.8428 no . .
C9 H7 3.4920 no . .
C9 H15 2.8065 no . .
C9 H17 2.8741 no . .
C10 H9A 3.0556 no . .
C10 H9C 3.0794 no . .
C10 H12 3.2629 no . .
C10 H14 3.2627 no . .
C10 H17 3.5818 no . .
C11 H13 3.2587 no . .
C11 H15 3.2820 no . .
C12 H14 3.2513 no . .
C13 H11 3.2608 no . .
C13 H15 3.2617 no . .
C14 H12 3.2515 no . .
C15 H9A 2.9496 no . .
C15 H9C 3.3079 no . .
C15 H11 3.2817 no . .
C15 H13 3.2596 no . .
C15 H17 3.4592 no . .
C16 H2 2.7600 no . .
C16 H18 3.2752 no . .
C16 H20 3.2772 no . .
C17 H9A 3.1580 no . .
C17 H15 3.5310 no . .
C17 H19 3.2637 no . .
C17 H21 3.2695 no . .
C18 H20 3.2576 no . .
C19 H17 3.2610 no . .
C19 H21 3.2626 no . .
C20 H18 3.2587 no . .
C21 H2 2.8599 no . .
C21 H17 3.2696 no . .
C21 H19 3.2635 no . .
H2 H4 2.7170 no . .
H2 H21 2.4119 no . .
H4 H5 2.3424 no . .
H5 H6 2.3249 no . .
H6 H7 2.3585 no . .
H7 H9C 3.0652 no . .
H7 H11 3.4646 no . .
H9A H15 2.3064 no . .
H9A H17 2.2791 no . .
H9B H17 3.1306 no . .
H9C H15 2.9753 no . .
H11 H12 2.3411 no . .
H12 H13 2.3259 no . .
H13 H14 2.3251 no . .
H14 H15 2.3419 no . .
H15 H17 2.9272 no . .
H17 H18 2.3352 no . .
H18 H19 2.3370 no . .
H19 H20 2.3354 no . .
H20 H21 2.3323 no . .
I1 H2 3.3018 no . 3_666
I1 H4 3.5885 no . 3_666
I1 H6 3.0816 no . 1_454
I1 H7 2.9592 no . 4_464
I1 H9A 3.1696 no . .
I1 H9C 3.1900 no . 4_464
I1 H12 3.0344 no . 1_554
I1 H13 3.0254 no . 4_564
I1 H15 3.1945 no . .
I1 H17 3.0862 no . .
I1 H18 3.3846 no . .
I1 H20 3.5568 no . 3_566
C1 H17 3.4469 no . 3_666
C2 H17 3.3832 no . 3_666
C3 H18 3.2984 no . 3_666
C4 H5 3.2908 no . 3_767
C4 H11 3.3583 no . 3_667
C4 H18 3.4497 no . 3_666
C5 H4 3.5855 no . 3_767
C5 H5 3.3308 no . 3_767
C5 H18 3.4666 no . 1_656
C5 H21 3.0459 no . 3_667
C6 H12 3.5779 no . 1_655
C6 H15 3.5732 no . 4_565
C6 H21 3.2909 no . 3_667
C7 H14 3.2711 no . 4_565
C7 H15 3.3458 no . 4_565
C9 H12 3.2811 no . 4_564
C9 H13 3.2863 no . 4_564
C10 H19 3.2803 no . 3_566
C11 H4 3.0188 no . 3_667
C11 H14 3.2902 no . 4_565
C11 H19 3.5834 no . 3_566
C12 H4 3.4005 no . 3_667
C12 H9C 3.2574 no . 4_465
C12 H19 3.5602 no . 3_566
C13 H9A 3.5037 no . 4_465
C13 H9C 3.5621 no . 4_465
C13 H19 3.2423 no . 3_566
C13 H21 3.4707 no . 2_556
C14 H7 3.4968 no . 4_464
C14 H19 2.9137 no . 3_566
C14 H20 3.2987 no . 3_566
C15 H6 3.3558 no . 4_464
C15 H7 3.3252 no . 4_464
C15 H19 2.9343 no . 3_566
C15 H20 3.4047 no . 3_566
C16 H9B 2.7555 no . 3_666
C16 H19 3.5813 no . 3_566
C17 H9B 2.7867 no . 3_666
C17 H19 3.5314 no . 3_566
C18 H5 3.4108 no . 1_454
C18 H9B 2.8066 no . 3_666
C19 H9B 2.8005 no . 3_666
C20 H9B 2.7842 no . 3_666
C20 H18 3.4623 no . 3_566
C21 H5 3.4324 no . 3_667
C21 H9B 2.7598 no . 3_666
H2 I1 3.3018 no . 3_666
H2 H11 3.1923 no . 3_667
H2 H13 3.4141 no . 2_546
H2 H17 3.4488 no . 3_666
H4 I1 3.5885 no . 3_666
H4 C5 3.5855 no . 3_767
H4 C11 3.0188 no . 3_667
H4 C12 3.4005 no . 3_667
H4 H5 3.1893 no . 3_767
H4 H11 2.5658 no . 3_667
H4 H12 3.2692 no . 3_667
H5 C4 3.2908 no . 3_767
H5 C5 3.3308 no . 3_767
H5 C18 3.4108 no . 1_656
H5 C21 3.4324 no . 3_667
H5 H4 3.1893 no . 3_767
H5 H5 3.2567 no . 3_767
H5 H18 2.5216 no . 1_656
H5 H21 2.9735 no . 3_667
H6 I1 3.0816 no . 1_656
H6 C15 3.3558 no . 4_565
H6 H9C 3.2635 no . 4_565
H6 H12 2.9761 no . 1_655
H6 H15 3.1359 no . 4_565
H6 H21 3.3787 no . 3_667
H7 I1 2.9592 no . 4_565
H7 C14 3.4968 no . 4_565
H7 C15 3.3252 no . 4_565
H7 H13 3.3567 no . 1_655
H7 H14 3.0379 no . 4_565
H7 H15 2.7014 no . 4_565
H9A I1 3.1696 no . .
H9A C13 3.5037 no . 4_564
H9A H12 3.3797 no . 4_564
H9A H13 2.7519 no . 4_564
H9B C16 2.7555 no . 3_666
H9B C17 2.7867 no . 3_666
H9B C18 2.8066 no . 3_666
H9B C19 2.8005 no . 3_666
H9B C20 2.7842 no . 3_666
H9B C21 2.7598 no . 3_666
H9B H12 3.4967 no . 4_564
H9B H13 3.4577 no . 4_564
H9B H17 3.3736 no . 3_666
H9B H18 3.3943 no . 3_666
H9B H19 3.3787 no . 3_666
H9B H20 3.3666 no . 3_666
H9B H21 3.3322 no . 3_666
H9C I1 3.1900 no . 4_565
H9C C12 3.2574 no . 4_564
H9C C13 3.5621 no . 4_564
H9C H6 3.2635 no . 4_464
H9C H12 2.5287 no . 4_564
H9C H13 3.1457 no . 4_564
H11 C4 3.3583 no . 3_667
H11 H2 3.1923 no . 3_667
H11 H4 2.5658 no . 3_667
H11 H14 2.8329 no . 4_565
H12 I1 3.0344 no . 1_556
H12 C6 3.5779 no . 1_455
H12 C9 3.2811 no . 4_465
H12 H4 3.2692 no . 3_667
H12 H6 2.9761 no . 1_455
H12 H9A 3.3797 no . 4_465
H12 H9B 3.4967 no . 4_465
H12 H9C 2.5287 no . 4_465
H12 H14 3.5332 no . 4_565
H13 I1 3.0254 no . 4_465
H13 C9 3.2863 no . 4_465
H13 H2 3.4141 no . 2_556
H13 H7 3.3567 no . 1_455
H13 H9A 2.7519 no . 4_465
H13 H9B 3.4577 no . 4_465
H13 H9C 3.1457 no . 4_465
H13 H21 3.4084 no . 2_556
H14 C7 3.2711 no . 4_464
H14 C11 3.2902 no . 4_464
H14 H7 3.0379 no . 4_464
H14 H11 2.8329 no . 4_464
H14 H12 3.5332 no . 4_464
H14 H19 3.2492 no . 3_566
H14 H20 2.9884 no . 3_566
H15 I1 3.1945 no . .
H15 C6 3.5732 no . 4_464
H15 C7 3.3458 no . 4_464
H15 H6 3.1359 no . 4_464
H15 H7 2.7014 no . 4_464
H15 H19 3.2811 no . 3_566
H15 H20 3.1870 no . 3_566
H17 I1 3.0862 no . .
H17 C1 3.4469 no . 3_666
H17 C2 3.3832 no . 3_666
H17 H2 3.4488 no . 3_666
H17 H9B 3.3736 no . 3_666
H18 I1 3.3846 no . .
H18 C3 3.2984 no . 3_666
H18 C4 3.4497 no . 3_666
H18 C5 3.4666 no . 1_454
H18 C20 3.4623 no . 3_566
H18 H5 2.5216 no . 1_454
H18 H9B 3.3943 no . 3_666
H18 H20 3.5380 no . 3_566
H19 C10 3.2803 no . 3_566
H19 C11 3.5834 no . 3_566
H19 C12 3.5602 no . 3_566
H19 C13 3.2423 no . 3_566
H19 C14 2.9137 no . 3_566
H19 C15 2.9343 no . 3_566
H19 C16 3.5813 no . 3_566
H19 C17 3.5314 no . 3_566
H19 H9B 3.3787 no . 3_666
H19 H14 3.2492 no . 3_566
H19 H15 3.2811 no . 3_566
H20 I1 3.5568 no . 3_566
H20 C14 3.2987 no . 3_566
H20 C15 3.4047 no . 3_566
H20 H9B 3.3666 no . 3_666
H20 H14 2.9884 no . 3_566
H20 H15 3.1870 no . 3_566
H20 H18 3.5380 no . 3_566
H21 C5 3.0459 no . 3_667
H21 C6 3.2909 no . 3_667
H21 C13 3.4707 no . 2_546
H21 H5 2.9735 no . 3_667
H21 H6 3.3787 no . 3_667
H21 H9B 3.3322 no . 3_666
H21 H13 3.4084 no . 2_546

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        YK_PMe_I
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane-methanol'
