# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dg153

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 P'
_chemical_formula_sum            'C24 H21 P'
_chemical_formula_weight         340.38

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '

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

_cell_length_a                   7.6281(5)
_cell_length_b                   29.8493(19)
_cell_length_c                   8.0370(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.421(4)
_cell_angle_gamma                90.00
_cell_volume                     1821.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2381
_cell_measurement_theta_min      1.364
_cell_measurement_theta_max      22.498

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.320
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.479
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
'SADABS. Bruker Nonius area detector scaling and absorption correction - V2.10, Bruker AXS Inc., Madison, Wisconsin, USA (2003).'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2381
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         22.50
_reflns_number_total             2381
_reflns_number_gt                2128
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0378P)²+2.8401P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    calc
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2381
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1373
_refine_ls_wR_factor_gt          0.1347
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_restrained_S_all      1.198
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2966(4) 0.37899(10) 0.9839(4) 0.0225(8) Uani 1 1 d . . .
C2 C 0.3145(4) 0.39752(10) 1.1549(4) 0.0224(8) Uani 1 1 d . . .
C3 C 0.3349(4) 0.36824(11) 1.2915(4) 0.0246(8) Uani 1 1 d . . .
H3 H 0.3289 0.3375 1.2725 0.030 Uiso 1 1 calc R . .
C4 C 0.3637(4) 0.38375(12) 1.4532(4) 0.0290(8) Uani 1 1 d . . .
H4 H 0.3750 0.3637 1.5421 0.035 Uiso 1 1 calc R . .
C5 C 0.3757(4) 0.42930(12) 1.4824(4) 0.0322(9) Uani 1 1 d . . .
H5 H 0.3976 0.4401 1.5909 0.039 Uiso 1 1 calc R . .
C6 C 0.3549(4) 0.45872(12) 1.3499(4) 0.0299(9) Uani 1 1 d . . .
H6 H 0.3646 0.4893 1.3709 0.036 Uiso 1 1 calc R . .
C7 C 0.3198(4) 0.44415(11) 1.1850(4) 0.0235(8) Uani 1 1 d . . .
C8 C 0.2974(4) 0.47793(11) 1.0533(5) 0.0303(9) Uani 1 1 d . . .
H8 H 0.3523 0.5052 1.0784 0.036 Uiso 1 1 calc R . .
C9 C 0.2095(5) 0.47518(11) 0.9026(5) 0.0302(9) Uani 1 1 d . . .
H9 H 0.2122 0.5009 0.8376 0.036 Uiso 1 1 calc R . .
C10 C 0.1095(4) 0.43797(11) 0.8241(4) 0.0249(8) Uani 1 1 d . . .
C11 C -0.0253(5) 0.44766(12) 0.6987(4) 0.0304(9) Uani 1 1 d . . .
H11 H -0.0446 0.4773 0.6661 0.037 Uiso 1 1 calc R . .
C12 C -0.1300(5) 0.41469(12) 0.6224(5) 0.0355(9) Uani 1 1 d . . .
H12 H -0.2194 0.4221 0.5402 0.043 Uiso 1 1 calc R . .
C13 C -0.1019(5) 0.37055(12) 0.6685(4) 0.0328(9) Uani 1 1 d . . .
H13 H -0.1738 0.3481 0.6191 0.039 Uiso 1 1 calc R . .
C14 C 0.0340(4) 0.35975(11) 0.7885(4) 0.0274(8) Uani 1 1 d . . .
H14 H 0.0533 0.3299 0.8178 0.033 Uiso 1 1 calc R . .
C15 C 0.1427(4) 0.39268(11) 0.8665(4) 0.0237(8) Uani 1 1 d . . .
C16 C 0.6038(4) 0.32569(10) 1.0672(4) 0.0211(8) Uani 1 1 d . . .
C17 C 0.6054(4) 0.28032(10) 1.1169(4) 0.0225(8) Uani 1 1 d . . .
C18 C 0.4589(4) 0.24891(11) 1.0548(4) 0.0282(8) Uani 1 1 d . . .
H18A H 0.4866 0.2191 1.0940 0.042 Uiso 1 1 calc R . .
H18B H 0.4457 0.2491 0.9348 0.042 Uiso 1 1 calc R . .
H18C H 0.3509 0.2585 1.0960 0.042 Uiso 1 1 calc R . .
C19 C 0.7412(4) 0.26502(11) 1.2288(4) 0.0238(8) Uani 1 1 d . . .
H19 H 0.7405 0.2353 1.2632 0.029 Uiso 1 1 calc R . .
C20 C 0.8781(4) 0.29257(11) 1.2912(4) 0.0238(8) Uani 1 1 d . . .
C21 C 1.0286(5) 0.27432(12) 1.4072(4) 0.0304(8) Uani 1 1 d . . .
H21A H 1.1128 0.2602 1.3427 0.046 Uiso 1 1 calc R . .
H21B H 0.9842 0.2528 1.4813 0.046 Uiso 1 1 calc R . .
H21C H 1.0843 0.2984 1.4713 0.046 Uiso 1 1 calc R . .
C22 C 0.8753(4) 0.33692(11) 1.2411(4) 0.0244(8) Uani 1 1 d . . .
H22 H 0.9654 0.3559 1.2836 0.029 Uiso 1 1 calc R . .
C23 C 0.7414(4) 0.35414(10) 1.1286(4) 0.0228(8) Uani 1 1 d . . .
C24 C 0.7476(5) 0.40272(11) 1.0806(5) 0.0306(9) Uani 1 1 d . . .
H24A H 0.6634 0.4192 1.1376 0.046 Uiso 1 1 calc R . .
H24B H 0.7200 0.4056 0.9620 0.046 Uiso 1 1 calc R . .
H24C H 0.8635 0.4143 1.1113 0.046 Uiso 1 1 calc R . .
P1 P 0.43405(12) 0.34222(3) 0.90261(11) 0.0259(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
C1 C2 1.476(5) . ?
C1 C15 1.492(5) . ?
C1 P1 1.691(3) . ?
C2 C3 1.400(5) . ?
C2 C7 1.413(5) . ?
C3 C4 1.378(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.460(5) . ?
C8 C9 1.330(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.457(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.400(5) . ?
C10 C15 1.411(5) . ?
C11 C12 1.375(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.396(5) . ?
C14 H14 0.9300 . ?
C16 C23 1.403(5) . ?
C16 C17 1.412(5) . ?
C16 P1 1.829(3) . ?
C17 C19 1.383(5) . ?
C17 C18 1.507(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.386(5) . ?
C19 H19 0.9300 . ?
C20 C22 1.383(5) . ?
C20 C21 1.510(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.396(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.502(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C15 119.0(3) . . ?
C2 C1 P1 126.6(2) . . ?
C15 C1 P1 114.4(2) . . ?
C3 C2 C7 118.8(3) . . ?
C3 C2 C1 119.3(3) . . ?
C7 C2 C1 121.8(3) . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 122.2(3) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C2 118.0(3) . . ?
C6 C7 C8 118.1(3) . . ?
C2 C7 C8 123.8(3) . . ?
C9 C8 C7 129.2(3) . . ?
C9 C8 H8 115.4 . . ?
C7 C8 H8 115.4 . . ?
C8 C9 C10 129.8(3) . . ?
C8 C9 H9 115.1 . . ?
C10 C9 H9 115.1 . . ?
C11 C10 C15 118.3(3) . . ?
C11 C10 C9 118.2(3) . . ?
C15 C10 C9 123.4(3) . . ?
C12 C11 C10 122.0(3) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 121.5(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 118.7(3) . . ?
C14 C15 C1 119.3(3) . . ?
C10 C15 C1 121.9(3) . . ?
C23 C16 C17 119.7(3) . . ?
C23 C16 P1 123.1(2) . . ?
C17 C16 P1 116.7(2) . . ?
C19 C17 C16 119.1(3) . . ?
C19 C17 C18 119.8(3) . . ?
C16 C17 C18 121.1(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 C20 122.1(3) . . ?
C17 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C22 C20 C19 118.2(3) . . ?
C22 C20 C21 121.0(3) . . ?
C19 C20 C21 120.8(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 C23 122.1(3) . . ?
C20 C22 H22 119.0 . . ?
C23 C22 H22 119.0 . . ?
C22 C23 C16 118.8(3) . . ?
C22 C23 C24 118.9(3) . . ?
C16 C23 C24 122.3(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 P1 C16 108.53(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 C1 C2 C3 126.4(3) . . . . ?
P1 C1 C2 C3 -53.0(4) . . . . ?
C15 C1 C2 C7 -56.6(4) . . . . ?
P1 C1 C2 C7 124.1(3) . . . . ?
C7 C2 C3 C4 -1.4(5) . . . . ?
C1 C2 C3 C4 175.7(3) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C3 C4 C5 C6 1.4(5) . . . . ?
C4 C5 C6 C7 0.8(5) . . . . ?
C5 C6 C7 C2 -3.2(5) . . . . ?
C5 C6 C7 C8 179.1(3) . . . . ?
C3 C2 C7 C6 3.4(5) . . . . ?
C1 C2 C7 C6 -173.6(3) . . . . ?
C3 C2 C7 C8 -179.0(3) . . . . ?
C1 C2 C7 C8 4.0(5) . . . . ?
C6 C7 C8 C9 -155.2(4) . . . . ?
C2 C7 C8 C9 27.3(6) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C8 C9 C10 C11 154.7(4) . . . . ?
C8 C9 C10 C15 -25.9(6) . . . . ?
C15 C10 C11 C12 3.0(5) . . . . ?
C9 C10 C11 C12 -177.6(3) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C11 C12 C13 C14 -1.4(5) . . . . ?
C12 C13 C14 C15 0.9(5) . . . . ?
C13 C14 C15 C10 1.5(5) . . . . ?
C13 C14 C15 C1 -174.7(3) . . . . ?
C11 C10 C15 C14 -3.4(5) . . . . ?
C9 C10 C15 C14 177.3(3) . . . . ?
C11 C10 C15 C1 172.8(3) . . . . ?
C9 C10 C15 C1 -6.6(5) . . . . ?
C2 C1 C15 C14 -125.6(3) . . . . ?
P1 C1 C15 C14 53.8(4) . . . . ?
C2 C1 C15 C10 58.3(4) . . . . ?
P1 C1 C15 C10 -122.3(3) . . . . ?
C23 C16 C17 C19 1.6(5) . . . . ?
P1 C16 C17 C19 173.7(2) . . . . ?
C23 C16 C17 C18 179.4(3) . . . . ?
P1 C16 C17 C18 -8.5(4) . . . . ?
C16 C17 C19 C20 -1.4(5) . . . . ?
C18 C17 C19 C20 -179.3(3) . . . . ?
C17 C19 C20 C22 1.2(5) . . . . ?
C17 C19 C20 C21 -177.2(3) . . . . ?
C19 C20 C22 C23 -1.1(5) . . . . ?
C21 C20 C22 C23 177.3(3) . . . . ?
C20 C22 C23 C16 1.2(5) . . . . ?
C20 C22 C23 C24 179.9(3) . . . . ?
C17 C16 C23 C22 -1.5(5) . . . . ?
P1 C16 C23 C22 -173.0(2) . . . . ?
C17 C16 C23 C24 179.9(3) . . . . ?
P1 C16 C23 C24 8.4(4) . . . . ?
C2 C1 P1 C16 3.9(3) . . . . ?
C15 C1 P1 C16 -175.5(2) . . . . ?
C23 C16 P1 C1 -73.1(3) . . . . ?
C17 C16 P1 C1 115.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        22.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.056
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes'
_chemical_properties_physical    Air-sensitive
_database_code_depnum_ccdc_archive 'CCDC 1013549'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dg074_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H23 P'
_chemical_formula_sum            'C26 H23 P'
_chemical_formula_weight         366.41

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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                   12.054(5)
_cell_length_b                   9.298(5)
_cell_length_c                   18.724(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 99.348(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2070.7(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4928
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      27.9

_exptl_crystal_description       irregular
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          1.1
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 APEX 2'
_diffrn_measurement_method       'area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13929
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         27.90
_reflns_number_total             4928
_reflns_number_gt                3787
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0432P)²+0.7756P] 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         4928
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.70630(12) -0.01269(18) 0.34104(8) 0.0320(3) Uani 1 1 d . . .
C2 C 0.70194(14) -0.16273(19) 0.34961(9) 0.0390(4) Uani 1 1 d . . .
C3 C 0.59267(18) -0.2443(2) 0.33290(12) 0.0550(5) Uani 1 1 d . . .
H3A H 0.5487 -0.2292 0.3719 0.082 Uiso 1 1 calc R . .
H3B H 0.6084 -0.3471 0.3288 0.082 Uiso 1 1 calc R . .
H3C H 0.5499 -0.2095 0.2871 0.082 Uiso 1 1 calc R . .
C4 C 0.80110(17) -0.2367(2) 0.37626(9) 0.0499(5) Uani 1 1 d . . .
H4 H 0.7986 -0.3382 0.3812 0.060 Uiso 1 1 calc R . .
C5 C 0.90260(16) -0.1664(3) 0.39557(10) 0.0513(5) Uani 1 1 d . . .
C6 C 1.00930(19) -0.2496(3) 0.42342(12) 0.0773(8) Uani 1 1 d . . .
H6A H 1.0524 -0.2640 0.3839 0.116 Uiso 1 1 calc R . .
H6B H 0.9896 -0.3433 0.4418 0.116 Uiso 1 1 calc R . .
H6C H 1.0548 -0.1953 0.4625 0.116 Uiso 1 1 calc R . .
C7 C 0.90500(14) -0.0192(2) 0.38709(9) 0.0477(5) Uani 1 1 d . . .
H7 H 0.9742 0.0301 0.4007 0.057 Uiso 1 1 calc R . .
C8 C 0.80962(13) 0.0600(2) 0.35929(9) 0.0387(4) Uani 1 1 d . . .
C9 C 0.82023(15) 0.2197(2) 0.34974(11) 0.0508(5) Uani 1 1 d . . .
H9A H 0.7989 0.2695 0.3916 0.076 Uiso 1 1 calc R . .
H9B H 0.7705 0.2502 0.3056 0.076 Uiso 1 1 calc R . .
H9C H 0.8982 0.2435 0.3457 0.076 Uiso 1 1 calc R . .
C10 C 0.53891(11) 0.19939(15) 0.35250(7) 0.0234(3) Uani 1 1 d . . .
C11 C 0.58838(11) 0.23110(14) 0.42860(7) 0.0220(3) Uani 1 1 d . . .
C12 C 0.62532(12) 0.12434(15) 0.47905(8) 0.0261(3) Uani 1 1 d . . .
H12 H 0.6191 0.0261 0.4650 0.031 Uiso 1 1 calc R . .
C13 C 0.67097(13) 0.15995(17) 0.54946(8) 0.0326(3) Uani 1 1 d . . .
H13 H 0.6956 0.0860 0.5833 0.039 Uiso 1 1 calc R . .
C14 C 0.68097(14) 0.30215(18) 0.57088(9) 0.0356(4) Uani 1 1 d . . .
H14 H 0.7126 0.3260 0.6192 0.043 Uiso 1 1 calc R . .
C15 C 0.64472(14) 0.40925(17) 0.52168(9) 0.0369(4) Uani 1 1 d . . .
H15 H 0.6520 0.5073 0.5360 0.044 Uiso 1 1 calc R . .
C16 C 0.59771(13) 0.37402(16) 0.45141(8) 0.0307(3) Uani 1 1 d . . .
H16 H 0.5714 0.4484 0.4182 0.037 Uiso 1 1 calc R . .
C17 C 0.44230(12) 0.29120(15) 0.31967(7) 0.0242(3) Uani 1 1 d . . .
C18 C 0.45023(14) 0.37549(17) 0.26036(8) 0.0338(3) Uani 1 1 d . . .
H18 H 0.5175 0.3742 0.2401 0.041 Uiso 1 1 calc R . .
C19 C 0.35980(15) 0.46422(19) 0.22901(9) 0.0408(4) Uani 1 1 d . . .
H19 H 0.3674 0.5223 0.1883 0.049 Uiso 1 1 calc R . .
C20 C 0.26261(14) 0.46711(18) 0.25647(9) 0.0372(4) Uani 1 1 d . . .
H20 H 0.2024 0.5264 0.2345 0.045 Uiso 1 1 calc R . .
C21 C 0.24967(12) 0.38287(15) 0.31754(8) 0.0280(3) Uani 1 1 d . . .
C22 C 0.14990(13) 0.38666(17) 0.34819(9) 0.0346(4) Uani 1 1 d . . .
H22 H 0.0895 0.4465 0.3271 0.042 Uiso 1 1 calc R . .
C23 C 0.13903(13) 0.30617(18) 0.40720(9) 0.0357(4) Uani 1 1 d . . .
H23 H 0.0719 0.3116 0.4276 0.043 Uiso 1 1 calc R . .
C24 C 0.22695(12) 0.21477(17) 0.43830(8) 0.0308(3) Uani 1 1 d . . .
H24 H 0.2183 0.1571 0.4789 0.037 Uiso 1 1 calc R . .
C25 C 0.32476(11) 0.20888(15) 0.41019(7) 0.0244(3) Uani 1 1 d . . .
H25 H 0.3834 0.1467 0.4316 0.029 Uiso 1 1 calc R . .
C26 C 0.34032(11) 0.29365(14) 0.34987(7) 0.0227(3) Uani 1 1 d . . .
P1 P 0.57949(3) 0.07750(5) 0.29514(2) 0.02996(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.406(3) . ?
C1 C8 1.409(2) . ?
C1 P1 1.8307(16) . ?
C2 C4 1.399(2) . ?
C2 C3 1.508(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C7 1.379(3) . ?
C5 C6 1.519(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.393(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.504(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.4821(19) . ?
C10 C17 1.4933(19) . ?
C10 P1 1.6876(15) . ?
C11 C12 1.3926(19) . ?
C11 C16 1.395(2) . ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.375(2) . ?
C17 C26 1.434(2) . ?
C18 C19 1.416(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.354(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.415(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.415(2) . ?
C21 C26 1.4261(19) . ?
C22 C23 1.358(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.409(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.368(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.414(2) . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C8 119.73(15) . . ?
C2 C1 P1 117.66(12) . . ?
C8 C1 P1 122.13(14) . . ?
C4 C2 C1 118.86(17) . . ?
C4 C2 C3 119.60(18) . . ?
C1 C2 C3 121.51(15) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C2 121.98(19) . . ?
C5 C4 H4 119.0 . . ?
C2 C4 H4 119.0 . . ?
C7 C5 C4 118.25(17) . . ?
C7 C5 C6 120.9(2) . . ?
C4 C5 C6 120.9(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 C8 122.41(18) . . ?
C5 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
C7 C8 C1 118.73(18) . . ?
C7 C8 C9 119.02(16) . . ?
C1 C8 C9 122.25(15) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C17 116.56(12) . . ?
C11 C10 P1 129.23(10) . . ?
C17 C10 P1 114.15(10) . . ?
C12 C11 C16 118.06(13) . . ?
C12 C11 C10 123.00(12) . . ?
C16 C11 C10 118.94(12) . . ?
C13 C12 C11 120.63(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.53(14) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 119.62(14) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.03(14) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 121.11(14) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C18 C17 C26 119.06(13) . . ?
C18 C17 C10 120.43(13) . . ?
C26 C17 C10 120.51(12) . . ?
C17 C18 C19 121.13(15) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C20 C19 C18 120.62(15) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 120.76(14) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C22 C21 C20 121.77(14) . . ?
C22 C21 C26 119.05(14) . . ?
C20 C21 C26 119.18(14) . . ?
C23 C22 C21 121.13(14) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 120.21(15) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 120.17(15) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 121.28(13) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C25 C26 C21 118.12(13) . . ?
C25 C26 C17 122.64(12) . . ?
C21 C26 C17 119.24(13) . . ?
C10 P1 C1 108.36(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
C8 C1 C2 C4 0.0(2) . . . . ?
P1 C1 C2 C4 172.16(12) . . . . ?
C8 C1 C2 C3 178.13(16) . . . . ?
P1 C1 C2 C3 -9.7(2) . . . . ?
C1 C2 C4 C5 1.2(3) . . . . ?
C3 C2 C4 C5 -176.99(17) . . . . ?
C2 C4 C5 C7 -0.9(3) . . . . ?
C2 C4 C5 C6 -179.18(16) . . . . ?
C4 C5 C7 C8 -0.7(3) . . . . ?
C6 C5 C7 C8 177.66(17) . . . . ?
C5 C7 C8 C1 1.8(3) . . . . ?
C5 C7 C8 C9 -178.19(17) . . . . ?
C2 C1 C8 C7 -1.4(2) . . . . ?
P1 C1 C8 C7 -173.22(12) . . . . ?
C2 C1 C8 C9 178.56(16) . . . . ?
P1 C1 C8 C9 6.8(2) . . . . ?
C17 C10 C11 C12 141.27(14) . . . . ?
P1 C10 C11 C12 -41.7(2) . . . . ?
C17 C10 C11 C16 -38.08(18) . . . . ?
P1 C10 C11 C16 138.99(13) . . . . ?
C16 C11 C12 C13 -0.7(2) . . . . ?
C10 C11 C12 C13 179.96(13) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C11 -1.5(3) . . . . ?
C12 C11 C16 C15 1.5(2) . . . . ?
C10 C11 C16 C15 -179.12(14) . . . . ?
C11 C10 C17 C18 118.38(15) . . . . ?
P1 C10 C17 C18 -59.13(16) . . . . ?
C11 C10 C17 C26 -61.11(17) . . . . ?
P1 C10 C17 C26 121.39(12) . . . . ?
C26 C17 C18 C19 0.1(2) . . . . ?
C10 C17 C18 C19 -179.39(14) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C18 C19 C20 C21 0.7(3) . . . . ?
C19 C20 C21 C22 178.52(15) . . . . ?
C19 C20 C21 C26 -0.4(2) . . . . ?
C20 C21 C22 C23 -179.41(15) . . . . ?
C26 C21 C22 C23 -0.5(2) . . . . ?
C21 C22 C23 C24 -1.2(2) . . . . ?
C22 C23 C24 C25 1.4(2) . . . . ?
C23 C24 C25 C26 0.1(2) . . . . ?
C24 C25 C26 C21 -1.8(2) . . . . ?
C24 C25 C26 C17 179.25(13) . . . . ?
C22 C21 C26 C25 2.00(19) . . . . ?
C20 C21 C26 C25 -179.09(13) . . . . ?
C22 C21 C26 C17 -179.02(13) . . . . ?
C20 C21 C26 C17 -0.1(2) . . . . ?
C18 C17 C26 C25 179.16(13) . . . . ?
C10 C17 C26 C25 -1.3(2) . . . . ?
C18 C17 C26 C21 0.2(2) . . . . ?
C10 C17 C26 C21 179.73(12) . . . . ?
C11 C10 P1 C1 -2.65(15) . . . . ?
C17 C10 P1 C1 174.47(10) . . . . ?
C2 C1 P1 C10 120.55(13) . . . . ?
C8 C1 P1 C10 -67.49(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.90
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.040
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes'
_chemical_properties_physical    Air-sensitive
_database_code_depnum_ccdc_archive 'CCDC 1013550'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dg095_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H25 P'
_chemical_formula_sum            'C30 H25 P'
_chemical_formula_weight         416.47

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   19.514(2)
_cell_length_b                   13.3010(14)
_cell_length_c                   20.028(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.5190(10)
_cell_angle_gamma                90.00
_cell_volume                     4523.6(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5459
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      28.1

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1760
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            47661
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         28.09
_reflns_number_total             5459
_reflns_number_gt                4278
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0581P)²+4.3843P] 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         5459
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1372
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.25824(10) -0.15614(14) 0.19509(10) 0.0416(4) Uani 1 1 d . . .
C2 C 0.25615(12) -0.13395(15) 0.26278(11) 0.0507(5) Uani 1 1 d . . .
C3 C 0.31526(17) -0.0648(2) 0.32311(13) 0.0772(8) Uani 1 1 d . . .
H16A H 0.3013 -0.0544 0.3634 0.116 Uiso 1 1 calc R . .
H16B H 0.3151 0.0000 0.2997 0.116 Uiso 1 1 calc R . .
H16C H 0.3678 -0.0949 0.3455 0.116 Uiso 1 1 calc R . .
C4 C 0.19889(13) -0.17881(17) 0.27532(11) 0.0540(5) Uani 1 1 d . . .
H12 H 0.1965 -0.1620 0.3202 0.065 Uiso 1 1 calc R . .
C5 C 0.14590(11) -0.24668(16) 0.22445(11) 0.0506(5) Uani 1 1 d . . .
C6 C 0.08422(14) -0.2946(2) 0.23891(15) 0.0720(7) Uani 1 1 d . . .
H15A H 0.0321 -0.2850 0.1939 0.108 Uiso 1 1 calc R . .
H15B H 0.0855 -0.2632 0.2837 0.108 Uiso 1 1 calc R . .
H15C H 0.0951 -0.3666 0.2485 0.108 Uiso 1 1 calc R . .
C7 C 0.15115(10) -0.27150(14) 0.15961(10) 0.0455(4) Uani 1 1 d . . .
H10 H 0.1158 -0.3200 0.1249 0.055 Uiso 1 1 calc R . .
C8 C 0.20624(10) -0.22778(13) 0.14405(10) 0.0402(4) Uani 1 1 d . . .
C9 C 0.21028(13) -0.25978(16) 0.07363(12) 0.0529(5) Uani 1 1 d . . .
H14A H 0.1741 -0.3161 0.0488 0.079 Uiso 1 1 calc R . .
H14B H 0.2641 -0.2807 0.0887 0.079 Uiso 1 1 calc R . .
H14C H 0.1952 -0.2032 0.0377 0.079 Uiso 1 1 calc R . .
C10 C 0.29383(10) -0.01258(12) 0.11391(9) 0.0363(3) Uani 1 1 d . . .
C11 C 0.34161(10) 0.03572(13) 0.08383(9) 0.0377(4) Uani 1 1 d . . .
C12 C 0.40460(11) -0.01323(15) 0.08389(11) 0.0486(4) Uani 1 1 d . . .
H3 H 0.4167 -0.0803 0.1023 0.058 Uiso 1 1 calc R . .
C13 C 0.45004(13) 0.03394(18) 0.05767(13) 0.0579(5) Uani 1 1 d . . .
H4 H 0.4935 -0.0005 0.0592 0.069 Uiso 1 1 calc R . .
C14 C 0.43274(12) 0.13021(18) 0.02944(12) 0.0581(5) Uani 1 1 d . . .
H5 H 0.4638 0.1624 0.0112 0.070 Uiso 1 1 calc R . .
C15 C 0.37044(12) 0.17930(16) 0.02790(13) 0.0572(5) Uani 1 1 d . . .
H6 H 0.3579 0.2456 0.0078 0.069 Uiso 1 1 calc R . .
C16 C 0.32535(11) 0.13351(14) 0.05528(11) 0.0468(4) Uani 1 1 d . . .
H7 H 0.2828 0.1692 0.0546 0.056 Uiso 1 1 calc R . .
C17 C 0.21498(9) 0.02982(12) 0.09077(9) 0.0336(3) Uani 1 1 d . . .
C18 C 0.15325(9) 0.03114(11) 0.01140(9) 0.0334(3) Uani 1 1 d . . .
C19 C 0.16462(11) -0.00884(13) -0.04794(9) 0.0403(4) Uani 1 1 d . . .
H19 H 0.2134 -0.0398 -0.0353 0.048 Uiso 1 1 calc R . .
C20 C 0.10671(12) -0.00383(16) -0.12318(10) 0.0476(4) Uani 1 1 d . . .
H20 H 0.1156 -0.0302 -0.1624 0.057 Uiso 1 1 calc R . .
C21 C 0.03501(11) 0.04011(15) -0.14173(10) 0.0480(4) Uani 1 1 d . . .
H21 H -0.0051 0.0441 -0.1939 0.058 Uiso 1 1 calc R . .
C22 C 0.02142(10) 0.07768(13) -0.08592(9) 0.0414(4) Uani 1 1 d . . .
H22 H -0.0285 0.1064 -0.1000 0.050 Uiso 1 1 calc R . .
C23 C 0.07979(9) 0.07488(11) -0.00776(9) 0.0340(3) Uani 1 1 d . . .
C24 C 0.06636(9) 0.11771(11) 0.05162(9) 0.0351(3) Uani 1 1 d . . .
C25 C -0.00513(10) 0.16203(13) 0.03734(11) 0.0423(4) Uani 1 1 d . . .
H25 H -0.0482 0.1637 -0.0136 0.051 Uiso 1 1 calc R . .
C26 C -0.01378(12) 0.20290(14) 0.09580(12) 0.0506(5) Uani 1 1 d . . .
H26 H -0.0626 0.2327 0.0845 0.061 Uiso 1 1 calc R . .
C27 C 0.04758(13) 0.20139(16) 0.17121(13) 0.0555(5) Uani 1 1 d . . .
H27 H 0.0410 0.2301 0.2111 0.067 Uiso 1 1 calc R . .
C28 C 0.11722(12) 0.15811(15) 0.18699(11) 0.0492(5) Uani 1 1 d . . .
H28 H 0.1591 0.1562 0.2385 0.059 Uiso 1 1 calc R . .
C29 C 0.12839(10) 0.11596(12) 0.12817(9) 0.0381(4) Uani 1 1 d . . .
C30 C 0.20121(10) 0.07196(13) 0.14494(9) 0.0382(4) Uani 1 1 d . . .
H30 H 0.2426 0.0719 0.1967 0.046 Uiso 1 1 calc R . .
P1 P 0.33602(3) -0.10631(4) 0.17876(3) 0.04899(16) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C8 1.400(3) . ?
C1 C2 1.408(3) . ?
C1 P1 1.8273(18) . ?
C2 C4 1.394(3) . ?
C2 C3 1.505(3) . ?
C3 H16A 0.9800 . ?
C3 H16B 0.9800 . ?
C3 H16C 0.9800 . ?
C4 C5 1.373(3) . ?
C4 H12 0.9500 . ?
C5 C7 1.392(3) . ?
C5 C6 1.511(3) . ?
C6 H15A 0.9800 . ?
C6 H15B 0.9800 . ?
C6 H15C 0.9800 . ?
C7 C8 1.386(2) . ?
C7 H10 0.9500 . ?
C8 C9 1.512(3) . ?
C9 H14A 0.9800 . ?
C9 H14B 0.9800 . ?
C9 H14C 0.9800 . ?
C10 C17 1.483(2) . ?
C10 C11 1.483(2) . ?
C10 P1 1.6926(16) . ?
C11 C12 1.390(3) . ?
C11 C16 1.393(2) . ?
C12 C13 1.384(3) . ?
C12 H3 0.9500 . ?
C13 C14 1.373(3) . ?
C13 H4 0.9500 . ?
C14 C15 1.367(3) . ?
C14 H5 0.9500 . ?
C15 C16 1.386(3) . ?
C15 H6 0.9500 . ?
C16 H7 0.9500 . ?
C17 C30 1.360(2) . ?
C17 C18 1.446(2) . ?
C18 C23 1.414(2) . ?
C18 C19 1.416(2) . ?
C19 C20 1.369(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.364(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.411(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.454(2) . ?
C24 C25 1.408(2) . ?
C24 C29 1.410(2) . ?
C25 C26 1.375(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.390(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.362(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.415(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.416(2) . ?
C30 H30 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C1 C2 119.42(17) . . ?
C8 C1 P1 118.90(14) . . ?
C2 C1 P1 121.14(15) . . ?
C4 C2 C1 119.33(19) . . ?
C4 C2 C3 118.8(2) . . ?
C1 C2 C3 121.8(2) . . ?
C2 C3 H16A 109.5 . . ?
C2 C3 H16B 109.5 . . ?
H16A C3 H16B 109.5 . . ?
C2 C3 H16C 109.5 . . ?
H16A C3 H16C 109.5 . . ?
H16B C3 H16C 109.5 . . ?
C5 C4 C2 121.69(18) . . ?
C5 C4 H12 119.2 . . ?
C2 C4 H12 119.2 . . ?
C4 C5 C7 118.27(18) . . ?
C4 C5 C6 121.0(2) . . ?
C7 C5 C6 120.7(2) . . ?
C5 C6 H15A 109.5 . . ?
C5 C6 H15B 109.5 . . ?
H15A C6 H15B 109.5 . . ?
C5 C6 H15C 109.5 . . ?
H15A C6 H15C 109.5 . . ?
H15B C6 H15C 109.5 . . ?
C8 C7 C5 122.15(19) . . ?
C8 C7 H10 118.9 . . ?
C5 C7 H10 118.9 . . ?
C7 C8 C1 119.01(17) . . ?
C7 C8 C9 119.63(17) . . ?
C1 C8 C9 121.35(16) . . ?
C8 C9 H14A 109.5 . . ?
C8 C9 H14B 109.5 . . ?
H14A C9 H14B 109.5 . . ?
C8 C9 H14C 109.5 . . ?
H14A C9 H14C 109.5 . . ?
H14B C9 H14C 109.5 . . ?
C17 C10 C11 118.14(13) . . ?
C17 C10 P1 123.89(12) . . ?
C11 C10 P1 117.74(12) . . ?
C12 C11 C16 117.39(16) . . ?
C12 C11 C10 121.96(15) . . ?
C16 C11 C10 120.65(16) . . ?
C13 C12 C11 121.26(18) . . ?
C13 C12 H3 119.4 . . ?
C11 C12 H3 119.4 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H4 119.8 . . ?
C12 C13 H4 119.8 . . ?
C15 C14 C13 119.37(19) . . ?
C15 C14 H5 120.3 . . ?
C13 C14 H5 120.3 . . ?
C14 C15 C16 120.80(19) . . ?
C14 C15 H6 119.6 . . ?
C16 C15 H6 119.6 . . ?
C15 C16 C11 120.80(18) . . ?
C15 C16 H7 119.6 . . ?
C11 C16 H7 119.6 . . ?
C30 C17 C18 119.13(15) . . ?
C30 C17 C10 119.32(14) . . ?
C18 C17 C10 121.50(14) . . ?
C23 C18 C19 118.96(14) . . ?
C23 C18 C17 119.17(14) . . ?
C19 C18 C17 121.86(15) . . ?
C20 C19 C18 121.32(17) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 119.46(17) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C22 C21 C20 120.82(16) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 121.49(17) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C22 C23 C18 117.92(15) . . ?
C22 C23 C24 121.62(15) . . ?
C18 C23 C24 120.43(14) . . ?
C25 C24 C29 117.50(16) . . ?
C25 C24 C23 123.90(15) . . ?
C29 C24 C23 118.60(15) . . ?
C26 C25 C24 121.18(17) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C25 C26 C27 121.20(18) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C28 C27 C26 119.01(18) . . ?
C28 C27 H27 120.5 . . ?
C26 C27 H27 120.5 . . ?
C27 C28 C29 121.31(18) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 H28 119.3 . . ?
C24 C29 C28 119.79(17) . . ?
C24 C29 C30 119.24(15) . . ?
C28 C29 C30 120.97(16) . . ?
C17 C30 C29 123.41(15) . . ?
C17 C30 H30 118.3 . . ?
C29 C30 H30 118.3 . . ?
C10 P1 C1 105.76(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C1 C2 C4 -4.2(3) . . . . ?
P1 C1 C2 C4 -175.76(14) . . . . ?
C8 C1 C2 C3 174.39(19) . . . . ?
P1 C1 C2 C3 2.8(3) . . . . ?
C1 C2 C4 C5 2.1(3) . . . . ?
C3 C2 C4 C5 -176.5(2) . . . . ?
C2 C4 C5 C7 1.0(3) . . . . ?
C2 C4 C5 C6 180.00(19) . . . . ?
C4 C5 C7 C8 -2.0(3) . . . . ?
C6 C5 C7 C8 178.99(17) . . . . ?
C5 C7 C8 C1 -0.1(3) . . . . ?
C5 C7 C8 C9 178.52(17) . . . . ?
C2 C1 C8 C7 3.2(2) . . . . ?
P1 C1 C8 C7 174.98(13) . . . . ?
C2 C1 C8 C9 -175.40(17) . . . . ?
P1 C1 C8 C9 -3.7(2) . . . . ?
C17 C10 C11 C12 -161.55(16) . . . . ?
P1 C10 C11 C12 23.7(2) . . . . ?
C17 C10 C11 C16 19.5(2) . . . . ?
P1 C10 C11 C16 -155.28(14) . . . . ?
C16 C11 C12 C13 0.9(3) . . . . ?
C10 C11 C12 C13 -178.09(18) . . . . ?
C11 C12 C13 C14 -1.3(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C11 -1.1(3) . . . . ?
C12 C11 C16 C15 0.2(3) . . . . ?
C10 C11 C16 C15 179.27(18) . . . . ?
C11 C10 C17 C30 -115.03(17) . . . . ?
P1 C10 C17 C30 59.3(2) . . . . ?
C11 C10 C17 C18 62.4(2) . . . . ?
P1 C10 C17 C18 -123.22(15) . . . . ?
C30 C17 C18 C23 -0.9(2) . . . . ?
C10 C17 C18 C23 -178.34(14) . . . . ?
C30 C17 C18 C19 178.14(15) . . . . ?
C10 C17 C18 C19 0.7(2) . . . . ?
C23 C18 C19 C20 1.5(2) . . . . ?
C17 C18 C19 C20 -177.56(16) . . . . ?
C18 C19 C20 C21 -0.8(3) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C20 C21 C22 C23 1.1(3) . . . . ?
C21 C22 C23 C18 -0.4(2) . . . . ?
C21 C22 C23 C24 178.02(16) . . . . ?
C19 C18 C23 C22 -0.9(2) . . . . ?
C17 C18 C23 C22 178.21(14) . . . . ?
C19 C18 C23 C24 -179.29(14) . . . . ?
C17 C18 C23 C24 -0.2(2) . . . . ?
C22 C23 C24 C25 2.0(2) . . . . ?
C18 C23 C24 C25 -179.62(15) . . . . ?
C22 C23 C24 C29 -177.42(15) . . . . ?
C18 C23 C24 C29 1.0(2) . . . . ?
C29 C24 C25 C26 0.6(2) . . . . ?
C23 C24 C25 C26 -178.83(16) . . . . ?
C24 C25 C26 C27 -0.4(3) . . . . ?
C25 C26 C27 C28 -0.3(3) . . . . ?
C26 C27 C28 C29 0.7(3) . . . . ?
C25 C24 C29 C28 -0.2(2) . . . . ?
C23 C24 C29 C28 179.30(15) . . . . ?
C25 C24 C29 C30 179.94(15) . . . . ?
C23 C24 C29 C30 -0.6(2) . . . . ?
C27 C28 C29 C24 -0.5(3) . . . . ?
C27 C28 C29 C30 179.38(18) . . . . ?
C18 C17 C30 C29 1.3(2) . . . . ?
C10 C17 C30 C29 178.81(15) . . . . ?
C24 C29 C30 C17 -0.6(2) . . . . ?
C28 C29 C30 C17 179.55(17) . . . . ?
C17 C10 P1 C1 11.37(16) . . . . ?
C11 C10 P1 C1 -174.23(13) . . . . ?
C8 C1 P1 C10 83.62(15) . . . . ?
C2 C1 P1 C10 -104.78(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        28.09
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.044
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes'
_database_code_depnum_ccdc_archive 'CCDC 1013551'
