# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

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

data_289
_database_code_depnum_ccdc_archive 'CCDC 1062715'
_audit_update_record             
;
2015-04-30 deposited with the CCDC.
2015-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H17 O3 P'
_chemical_formula_sum            'C26 H17 O3 P'
_chemical_formula_weight         408.37
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   8.4926(17)
_cell_length_b                   12.013(2)
_cell_length_c                   19.248(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1963.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8061
_cell_measurement_theta_min      3.68
_cell_measurement_theta_max      66.76

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    1.455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5721
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8910
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.34
_diffrn_reflns_theta_max         67.01
_reflns_number_total             3380
_reflns_number_gt                3338
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_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)+(0.0930P)²+0.1263P] 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     SHELXL
_refine_ls_extinction_coef       0.0020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(2)
_refine_ls_number_reflns         3380
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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 0.85919(6) 0.67986(5) 0.84138(2) 0.04452(19) Uani 1 1 d . . .
O1 O 0.82365(17) 0.57747(13) 0.79073(7) 0.0461(3) Uani 1 1 d . . .
O2 O 0.85799(19) 0.78517(12) 0.79113(8) 0.0515(4) Uani 1 1 d . . .
O3 O 0.75002(18) 0.68480(18) 0.89949(8) 0.0626(5) Uani 1 1 d . . .
C1 C 0.9263(2) 0.56085(15) 0.73496(10) 0.0418(4) Uani 1 1 d . . .
C2 C 0.8536(3) 0.52765(16) 0.67199(11) 0.0475(5) Uani 1 1 d . . .
C3 C 0.6890(3) 0.5126(2) 0.66579(13) 0.0588(6) Uani 1 1 d . . .
H3B H 0.6241 0.5224 0.7042 0.071 Uiso 1 1 calc R . .
C4 C 0.6258(4) 0.4838(2) 0.60317(15) 0.0726(7) Uani 1 1 d . . .
H4A H 0.5177 0.4734 0.5992 0.087 Uiso 1 1 calc R . .
C5 C 0.7227(5) 0.4698(3) 0.54467(14) 0.0773(8) Uani 1 1 d . . .
H5A H 0.6780 0.4515 0.5021 0.093 Uiso 1 1 calc R . .
C6 C 0.8787(4) 0.4825(2) 0.54981(13) 0.0727(8) Uani 1 1 d . . .
H6A H 0.9406 0.4721 0.5105 0.087 Uiso 1 1 calc R . .
C7 C 0.9529(3) 0.51162(18) 0.61375(12) 0.0550(6) Uani 1 1 d . . .
C8 C 1.1160(3) 0.5273(2) 0.62101(12) 0.0605(6) Uani 1 1 d . . .
H8A H 1.1813 0.5160 0.5829 0.073 Uiso 1 1 calc R . .
C9 C 1.1806(3) 0.5586(2) 0.68295(12) 0.0544(5) Uani 1 1 d . . .
H9A H 1.2891 0.5680 0.6860 0.065 Uiso 1 1 calc R . .
C10 C 1.0866(2) 0.57704(16) 0.74254(11) 0.0449(4) Uani 1 1 d . . .
C11 C 1.1546(3) 0.61158(16) 0.80959(10) 0.0447(4) Uani 1 1 d . . .
C12 C 1.3132(3) 0.5951(2) 0.82589(13) 0.0552(5) Uani 1 1 d . . .
H12A H 1.3798 0.5626 0.7934 0.066 Uiso 1 1 calc R . .
C13 C 1.3723(3) 0.6268(2) 0.89012(15) 0.0643(6) Uani 1 1 d . . .
H13A H 1.4786 0.6159 0.8997 0.077 Uiso 1 1 calc R . .
C14 C 1.2785(3) 0.6735(3) 0.93949(13) 0.0652(6) Uani 1 1 d . . .
H14A H 1.3201 0.6931 0.9825 0.078 Uiso 1 1 calc R . .
C15 C 1.1208(3) 0.6917(2) 0.92535(12) 0.0563(5) Uani 1 1 d . . .
H15A H 1.0557 0.7238 0.9586 0.068 Uiso 1 1 calc R . .
C16 C 1.0607(2) 0.66148(18) 0.86079(11) 0.0456(5) Uani 1 1 d . . .
C17 C 0.7402(3) 0.79867(17) 0.74061(12) 0.0502(5) Uani 1 1 d . . .
C18 C 0.5853(3) 0.7988(2) 0.75746(14) 0.0615(6) Uani 1 1 d . . .
H18A H 0.5542 0.7912 0.8035 0.074 Uiso 1 1 calc R . .
C19 C 0.4717(3) 0.8105(3) 0.70460(17) 0.0747(7) Uani 1 1 d . . .
H19A H 0.3651 0.8106 0.7156 0.090 Uiso 1 1 calc R . .
C20 C 0.5186(4) 0.8218(3) 0.63724(17) 0.0770(8) Uani 1 1 d . . .
H20A H 0.4429 0.8280 0.6026 0.092 Uiso 1 1 calc R . .
C21 C 0.6776(4) 0.8243(2) 0.61915(13) 0.0641(6) Uani 1 1 d . . .
C22 C 0.7304(6) 0.8372(3) 0.54993(16) 0.0900(10) Uani 1 1 d . . .
H22A H 0.6569 0.8408 0.5142 0.108 Uiso 1 1 calc R . .
C23 C 0.8859(6) 0.8443(3) 0.53450(18) 0.0959(12) Uani 1 1 d . . .
H23A H 0.9175 0.8544 0.4887 0.115 Uiso 1 1 calc R . .
C24 C 0.9980(5) 0.8367(3) 0.58661(18) 0.0862(9) Uani 1 1 d . . .
H24A H 1.1043 0.8420 0.5754 0.103 Uiso 1 1 calc R . .
C25 C 0.9542(3) 0.8216(2) 0.65441(14) 0.0656(6) Uani 1 1 d . . .
H25A H 1.0305 0.8163 0.6889 0.079 Uiso 1 1 calc R . .
C26 C 0.7945(3) 0.81412(18) 0.67177(12) 0.0527(5) 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 O3 1.4540(16) . ?
P1 O2 1.5925(16) . ?
P1 O1 1.5982(15) . ?
P1 C16 1.765(2) . ?
O1 C1 1.397(2) . ?
O2 C17 1.404(3) . ?
C1 C10 1.383(3) . ?
C1 C2 1.418(3) . ?
C2 C3 1.414(4) . ?
C2 C7 1.416(3) . ?
C3 C4 1.364(3) . ?
C3 H3B 0.9300 . ?
C4 C5 1.405(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.337(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.426(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.405(4) . ?
C8 C9 1.365(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.415(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.474(3) . ?
C11 C12 1.397(3) . ?
C11 C16 1.403(3) . ?
C12 C13 1.388(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.361(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.384(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.392(3) . ?
C15 H15A 0.9300 . ?
C17 C18 1.355(4) . ?
C17 C26 1.415(3) . ?
C18 C19 1.409(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.363(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.395(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.414(4) . ?
C21 C26 1.423(3) . ?
C22 C23 1.356(6) . ?
C22 H22A 0.9300 . ?
C23 C24 1.386(6) . ?
C23 H23A 0.9300 . ?
C24 C25 1.369(4) . ?
C24 H24A 0.9300 . ?
C25 C26 1.400(4) . ?
C25 H25A 0.9300 . ?

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
O3 P1 O2 115.51(10) . . ?
O3 P1 O1 112.34(10) . . ?
O2 P1 O1 103.87(7) . . ?
O3 P1 C16 117.41(10) . . ?
O2 P1 C16 103.54(9) . . ?
O1 P1 C16 102.47(9) . . ?
C1 O1 P1 117.44(12) . . ?
C17 O2 P1 121.13(14) . . ?
C10 C1 O1 120.87(18) . . ?
C10 C1 C2 124.0(2) . . ?
O1 C1 C2 115.18(18) . . ?
C3 C2 C7 120.3(2) . . ?
C3 C2 C1 122.6(2) . . ?
C7 C2 C1 117.1(2) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3B 120.1 . . ?
C2 C3 H3B 120.1 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C7 122.0(3) . . ?
C5 C6 H6A 119.0 . . ?
C7 C6 H6A 119.0 . . ?
C8 C7 C2 119.4(2) . . ?
C8 C7 C6 123.7(3) . . ?
C2 C7 C6 116.9(3) . . ?
C9 C8 C7 121.3(2) . . ?
C9 C8 H8A 119.3 . . ?
C7 C8 H8A 119.3 . . ?
C8 C9 C10 121.6(2) . . ?
C8 C9 H9A 119.2 . . ?
C10 C9 H9A 119.2 . . ?
C1 C10 C9 116.6(2) . . ?
C1 C10 C11 121.19(19) . . ?
C9 C10 C11 122.20(19) . . ?
C12 C11 C16 116.8(2) . . ?
C12 C11 C10 122.3(2) . . ?
C16 C11 C10 120.84(19) . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C14 C13 C12 121.5(2) . . ?
C14 C13 H13A 119.2 . . ?
C12 C13 H13A 119.2 . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H14A 120.2 . . ?
C15 C14 H14A 120.2 . . ?
C14 C15 C16 119.3(2) . . ?
C14 C15 H15A 120.3 . . ?
C16 C15 H15A 120.3 . . ?
C15 C16 C11 122.0(2) . . ?
C15 C16 P1 120.79(18) . . ?
C11 C16 P1 117.14(15) . . ?
C18 C17 O2 121.7(2) . . ?
C18 C17 C26 122.7(2) . . ?
O2 C17 C26 115.6(2) . . ?
C17 C18 C19 119.5(3) . . ?
C17 C18 H18A 120.3 . . ?
C19 C18 H18A 120.3 . . ?
C20 C19 C18 119.8(3) . . ?
C20 C19 H19A 120.1 . . ?
C18 C19 H19A 120.1 . . ?
C19 C20 C21 121.5(3) . . ?
C19 C20 H20A 119.2 . . ?
C21 C20 H20A 119.2 . . ?
C20 C21 C22 123.0(3) . . ?
C20 C21 C26 119.7(3) . . ?
C22 C21 C26 117.3(3) . . ?
C23 C22 C21 121.5(4) . . ?
C23 C22 H22A 119.3 . . ?
C21 C22 H22A 119.3 . . ?
C22 C23 C24 120.4(3) . . ?
C22 C23 H23A 119.8 . . ?
C24 C23 H23A 119.8 . . ?
C25 C24 C23 120.8(3) . . ?
C25 C24 H24A 119.6 . . ?
C23 C24 H24A 119.6 . . ?
C24 C25 C26 119.9(3) . . ?
C24 C25 H25A 120.0 . . ?
C26 C25 H25A 120.0 . . ?
C25 C26 C17 123.2(2) . . ?
C25 C26 C21 120.0(2) . . ?
C17 C26 C21 116.8(2) . . ?

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
O3 P1 O1 C1 -176.71(13) . . . . ?
O2 P1 O1 C1 57.77(14) . . . . ?
C16 P1 O1 C1 -49.79(15) . . . . ?
O3 P1 O2 C17 -78.89(17) . . . . ?
O1 P1 O2 C17 44.59(16) . . . . ?
C16 P1 O2 C17 151.34(16) . . . . ?
P1 O1 C1 C10 38.7(2) . . . . ?
P1 O1 C1 C2 -141.01(14) . . . . ?
C10 C1 C2 C3 -179.5(2) . . . . ?
O1 C1 C2 C3 0.2(3) . . . . ?
C10 C1 C2 C7 -0.7(3) . . . . ?
O1 C1 C2 C7 178.98(16) . . . . ?
C7 C2 C3 C4 -0.7(4) . . . . ?
C1 C2 C3 C4 178.0(2) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C3 C2 C7 C8 179.8(2) . . . . ?
C1 C2 C7 C8 1.0(3) . . . . ?
C3 C2 C7 C6 1.3(3) . . . . ?
C1 C2 C7 C6 -177.6(2) . . . . ?
C5 C6 C7 C8 -179.1(3) . . . . ?
C5 C6 C7 C2 -0.6(4) . . . . ?
C2 C7 C8 C9 -0.6(3) . . . . ?
C6 C7 C8 C9 177.9(2) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
O1 C1 C10 C9 -179.71(17) . . . . ?
C2 C1 C10 C9 -0.1(3) . . . . ?
O1 C1 C10 C11 0.4(3) . . . . ?
C2 C1 C10 C11 -179.97(18) . . . . ?
C8 C9 C10 C1 0.5(3) . . . . ?
C8 C9 C10 C11 -179.6(2) . . . . ?
C1 C10 C11 C12 159.2(2) . . . . ?
C9 C10 C11 C12 -20.7(3) . . . . ?
C1 C10 C11 C16 -19.7(3) . . . . ?
C9 C10 C11 C16 160.4(2) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
C10 C11 C12 C13 -178.7(2) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C15 -1.0(4) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C11 0.9(4) . . . . ?
C14 C15 C16 P1 178.4(2) . . . . ?
C12 C11 C16 C15 -1.1(3) . . . . ?
C10 C11 C16 C15 177.9(2) . . . . ?
C12 C11 C16 P1 -178.65(16) . . . . ?
C10 C11 C16 P1 0.4(3) . . . . ?
O3 P1 C16 C15 -23.5(2) . . . . ?
O2 P1 C16 C15 105.1(2) . . . . ?
O1 P1 C16 C15 -147.09(19) . . . . ?
O3 P1 C16 C11 154.11(17) . . . . ?
O2 P1 C16 C11 -77.29(18) . . . . ?
O1 P1 C16 C11 30.52(18) . . . . ?
P1 O2 C17 C18 55.7(3) . . . . ?
P1 O2 C17 C26 -125.43(18) . . . . ?
O2 C17 C18 C19 -178.8(2) . . . . ?
C26 C17 C18 C19 2.4(4) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C18 C19 C20 C21 -1.3(5) . . . . ?
C19 C20 C21 C22 -179.2(3) . . . . ?
C19 C20 C21 C26 0.4(5) . . . . ?
C20 C21 C22 C23 176.9(3) . . . . ?
C26 C21 C22 C23 -2.7(5) . . . . ?
C21 C22 C23 C24 1.4(6) . . . . ?
C22 C23 C24 C25 0.2(5) . . . . ?
C23 C24 C25 C26 -0.3(5) . . . . ?
C24 C25 C26 C17 -179.9(3) . . . . ?
C24 C25 C26 C21 -1.1(4) . . . . ?
C18 C17 C26 C25 175.6(2) . . . . ?
O2 C17 C26 C25 -3.3(3) . . . . ?
C18 C17 C26 C21 -3.2(3) . . . . ?
O2 C17 C26 C21 177.94(19) . . . . ?
C20 C21 C26 C25 -177.1(3) . . . . ?
C22 C21 C26 C25 2.6(4) . . . . ?
C20 C21 C26 C17 1.8(4) . . . . ?
C22 C21 C26 C17 -178.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        67.01
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.065
