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

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

data_z0924m
_database_code_depnum_ccdc_archive 'CCDC 1046595'
_audit_update_record             
;
2015-01-31 deposited with the CCDC.
2015-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H26 O3 P2'
_chemical_formula_weight         544.49

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_space_group_name_Hall           '-P 1'

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

_cell_length_a                   10.554(2)
_cell_length_b                   12.782(3)
_cell_length_c                   12.959(3)
_cell_angle_alpha                79.295(4)
_cell_angle_beta                 67.900(4)
_cell_angle_gamma                76.462(4)
_cell_volume                     1565.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9202
_exptl_absorpt_correction_T_max  0.9653
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5414
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5414
_reflns_number_gt                4812
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0596P)²+1.1193P] 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         5414
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1347
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.84176(6) 0.31832(5) 0.35630(5) 0.02924(17) Uani 1 1 d . . .
P2 P 0.63479(6) 0.34325(5) 0.22230(5) 0.03154(18) Uani 1 1 d . . .
O1 O 0.7780(2) 0.41405(14) 0.41789(15) 0.0413(4) Uani 1 1 d . . .
O2 O 0.62845(18) 0.28100(15) 0.13906(15) 0.0412(4) Uani 1 1 d . . .
O3 O 0.9960(2) 0.25555(19) -0.36242(18) 0.0623(6) Uani 1 1 d . . .
C1 C 0.8055(2) 0.32430(18) 0.2292(2) 0.0299(5) Uani 1 1 d . . .
C2 C 0.9252(2) 0.31440(18) 0.1400(2) 0.0304(5) Uani 1 1 d . . .
C3 C 1.0531(2) 0.29719(19) 0.1682(2) 0.0331(5) Uani 1 1 d . . .
C4 C 1.1891(3) 0.2832(2) 0.0949(2) 0.0411(6) Uani 1 1 d . . .
H4A H 1.2096 0.2824 0.0171 0.049 Uiso 1 1 calc R . .
C5 C 1.2951(3) 0.2704(2) 0.1375(3) 0.0501(7) Uani 1 1 d . . .
H5A H 1.3890 0.2615 0.0878 0.060 Uiso 1 1 calc R . .
C6 C 1.2674(3) 0.2703(2) 0.2493(3) 0.0499(7) Uani 1 1 d . . .
H6A H 1.3419 0.2610 0.2763 0.060 Uiso 1 1 calc R . .
C7 C 1.1323(3) 0.2837(2) 0.3234(2) 0.0390(6) Uani 1 1 d . . .
H7A H 1.1129 0.2831 0.4013 0.047 Uiso 1 1 calc R . .
C8 C 1.0261(3) 0.29786(19) 0.2820(2) 0.0321(5) Uani 1 1 d . . .
C9 C 0.8071(2) 0.19387(19) 0.4408(2) 0.0325(5) Uani 1 1 d . . .
C10 C 0.8652(3) 0.0954(2) 0.3982(2) 0.0428(6) Uani 1 1 d . . .
H10A H 0.9235 0.0928 0.3219 0.051 Uiso 1 1 calc R . .
C11 C 0.8385(3) 0.0011(2) 0.4664(3) 0.0574(8) Uani 1 1 d . . .
H11A H 0.8782 -0.0669 0.4377 0.069 Uiso 1 1 calc R . .
C12 C 0.7535(4) 0.0062(3) 0.5768(3) 0.0635(9) Uani 1 1 d . . .
H12A H 0.7353 -0.0589 0.6243 0.076 Uiso 1 1 calc R . .
C13 C 0.6955(4) 0.1027(3) 0.6186(3) 0.0653(9) Uani 1 1 d . . .
H13A H 0.6359 0.1047 0.6946 0.078 Uiso 1 1 calc R . .
C14 C 0.7222(3) 0.1980(2) 0.5517(2) 0.0478(7) Uani 1 1 d . . .
H14A H 0.6827 0.2655 0.5814 0.057 Uiso 1 1 calc R . .
C15 C 0.9349(2) 0.3216(2) 0.0221(2) 0.0324(5) Uani 1 1 d . . .
C16 C 0.8923(3) 0.4190(2) -0.0325(2) 0.0365(6) Uani 1 1 d . . .
H16A H 0.8595 0.4824 0.0050 0.044 Uiso 1 1 calc R . .
C17 C 0.8972(3) 0.4248(2) -0.1421(2) 0.0380(6) Uani 1 1 d . . .
H17A H 0.8669 0.4922 -0.1787 0.046 Uiso 1 1 calc R . .
C18 C 0.9455(2) 0.3338(2) -0.1983(2) 0.0350(5) Uani 1 1 d . . .
C19 C 0.9922(3) 0.2372(2) -0.1437(2) 0.0468(7) Uani 1 1 d . . .
H19A H 1.0278 0.1742 -0.1821 0.056 Uiso 1 1 calc R . .
C20 C 0.9881(3) 0.2304(2) -0.0362(2) 0.0443(6) Uani 1 1 d . . .
H20A H 1.0217 0.1634 -0.0010 0.053 Uiso 1 1 calc R . .
C21 C 0.9460(3) 0.3356(2) -0.3141(2) 0.0398(6) Uani 1 1 d . . .
C22 C 0.8830(4) 0.4362(3) -0.3674(2) 0.0566(8) Uani 1 1 d . . .
H22A H 0.8913 0.4247 -0.4426 0.085 Uiso 1 1 calc R . .
H22B H 0.9313 0.4949 -0.3730 0.085 Uiso 1 1 calc R . .
H22C H 0.7845 0.4555 -0.3220 0.085 Uiso 1 1 calc R . .
C23 C 0.5226(2) 0.30337(19) 0.3615(2) 0.0326(5) Uani 1 1 d . . .
C24 C 0.5220(3) 0.1938(2) 0.3930(2) 0.0412(6) Uani 1 1 d . . .
H24A H 0.5865 0.1426 0.3450 0.049 Uiso 1 1 calc R . .
C25 C 0.4286(3) 0.1586(2) 0.4935(3) 0.0453(7) Uani 1 1 d . . .
H25A H 0.4295 0.0833 0.5148 0.054 Uiso 1 1 calc R . .
C26 C 0.3340(3) 0.2321(2) 0.5631(2) 0.0462(7) Uani 1 1 d . . .
H26A H 0.2683 0.2076 0.6317 0.055 Uiso 1 1 calc R . .
C27 C 0.3344(3) 0.3411(2) 0.5336(2) 0.0442(6) Uani 1 1 d . . .
H27A H 0.2698 0.3917 0.5822 0.053 Uiso 1 1 calc R . .
C28 C 0.4289(3) 0.3772(2) 0.4330(2) 0.0384(6) Uani 1 1 d . . .
H28A H 0.4294 0.4525 0.4129 0.046 Uiso 1 1 calc R . .
C29 C 0.5798(2) 0.4866(2) 0.1948(2) 0.0342(5) Uani 1 1 d . . .
C30 C 0.4897(3) 0.5206(2) 0.1353(2) 0.0405(6) Uani 1 1 d . . .
H30A H 0.4606 0.4692 0.1087 0.049 Uiso 1 1 calc R . .
C31 C 0.4424(3) 0.6305(2) 0.1150(2) 0.0481(7) Uani 1 1 d . . .
H31A H 0.3802 0.6543 0.0747 0.058 Uiso 1 1 calc R . .
C32 C 0.4845(3) 0.7046(2) 0.1524(2) 0.0517(8) Uani 1 1 d . . .
H32A H 0.4526 0.7798 0.1374 0.062 Uiso 1 1 calc R . .
C33 C 0.5737(4) 0.6703(2) 0.2122(3) 0.0539(8) Uani 1 1 d . . .
H33A H 0.6017 0.7219 0.2394 0.065 Uiso 1 1 calc R . .
C34 C 0.6220(3) 0.5616(2) 0.2326(3) 0.0479(7) Uani 1 1 d . . .
H34A H 0.6845 0.5384 0.2727 0.057 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 O1 1.4698(18) . ?
P1 C9 1.785(2) . ?
P1 C8 1.796(3) . ?
P1 C1 1.811(2) . ?
P2 O2 1.4831(18) . ?
P2 C1 1.795(2) . ?
P2 C29 1.799(3) . ?
P2 C23 1.803(3) . ?
O3 C21 1.207(3) . ?
C1 C2 1.353(3) . ?
C2 C15 1.478(3) . ?
C2 C3 1.486(3) . ?
C3 C4 1.383(4) . ?
C3 C8 1.393(3) . ?
C4 C5 1.389(4) . ?
C5 C6 1.367(4) . ?
C6 C7 1.378(4) . ?
C7 C8 1.378(3) . ?
C9 C10 1.381(4) . ?
C9 C14 1.381(4) . ?
C10 C11 1.374(4) . ?
C11 C12 1.377(5) . ?
C12 C13 1.355(5) . ?
C13 C14 1.378(4) . ?
C15 C16 1.379(3) . ?
C15 C20 1.395(4) . ?
C16 C17 1.391(3) . ?
C17 C18 1.378(4) . ?
C18 C19 1.386(4) . ?
C18 C21 1.494(4) . ?
C19 C20 1.365(4) . ?
C21 C22 1.479(4) . ?
C23 C24 1.385(4) . ?
C23 C28 1.387(4) . ?
C24 C25 1.376(4) . ?
C25 C26 1.376(4) . ?
C26 C27 1.374(4) . ?
C27 C28 1.386(4) . ?
C29 C34 1.377(4) . ?
C29 C30 1.386(3) . ?
C30 C31 1.387(4) . ?
C31 C32 1.364(4) . ?
C32 C33 1.381(4) . ?
C33 C34 1.375(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C9 113.70(11) . . ?
O1 P1 C8 117.74(11) . . ?
C9 P1 C8 106.04(11) . . ?
O1 P1 C1 115.51(10) . . ?
C9 P1 C1 109.49(11) . . ?
C8 P1 C1 92.13(11) . . ?
O2 P2 C1 113.34(11) . . ?
O2 P2 C29 112.62(11) . . ?
C1 P2 C29 106.74(11) . . ?
O2 P2 C23 111.09(11) . . ?
C1 P2 C23 106.18(11) . . ?
C29 P2 C23 106.39(11) . . ?
C2 C1 P2 124.82(18) . . ?
C2 C1 P1 110.34(17) . . ?
P2 C1 P1 124.82(14) . . ?
C1 C2 C15 125.3(2) . . ?
C1 C2 C3 114.4(2) . . ?
C15 C2 C3 120.4(2) . . ?
C4 C3 C8 119.6(2) . . ?
C4 C3 C2 127.1(2) . . ?
C8 C3 C2 113.3(2) . . ?
C3 C4 C5 118.5(3) . . ?
C6 C5 C4 121.4(3) . . ?
C5 C6 C7 120.7(2) . . ?
C6 C7 C8 118.5(3) . . ?
C7 C8 C3 121.3(2) . . ?
C7 C8 P1 128.9(2) . . ?
C3 C8 P1 109.78(17) . . ?
C10 C9 C14 120.2(2) . . ?
C10 C9 P1 121.5(2) . . ?
C14 C9 P1 118.2(2) . . ?
C11 C10 C9 119.9(3) . . ?
C10 C11 C12 119.3(3) . . ?
C13 C12 C11 120.9(3) . . ?
C12 C13 C14 120.5(3) . . ?
C13 C14 C9 119.1(3) . . ?
C16 C15 C20 118.7(2) . . ?
C16 C15 C2 120.5(2) . . ?
C20 C15 C2 120.8(2) . . ?
C15 C16 C17 120.4(2) . . ?
C18 C17 C16 120.7(2) . . ?
C17 C18 C19 118.3(2) . . ?
C17 C18 C21 122.3(2) . . ?
C19 C18 C21 119.3(2) . . ?
C20 C19 C18 121.5(3) . . ?
C19 C20 C15 120.3(2) . . ?
O3 C21 C22 120.8(3) . . ?
O3 C21 C18 120.1(3) . . ?
C22 C21 C18 119.1(2) . . ?
C24 C23 C28 119.2(2) . . ?
C24 C23 P2 117.51(19) . . ?
C28 C23 P2 123.00(19) . . ?
C25 C24 C23 120.4(3) . . ?
C24 C25 C26 120.2(3) . . ?
C27 C26 C25 120.0(3) . . ?
C26 C27 C28 120.1(3) . . ?
C27 C28 C23 120.0(2) . . ?
C34 C29 C30 120.0(2) . . ?
C34 C29 P2 122.24(19) . . ?
C30 C29 P2 117.7(2) . . ?
C29 C30 C31 119.3(3) . . ?
C32 C31 C30 120.6(3) . . ?
C31 C32 C33 119.9(3) . . ?
C34 C33 C32 120.3(3) . . ?
C33 C34 C29 120.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.051

# SQUEEZE RESULTS (APPEND TO CIF)
_platon_squeeze_details          
;
SQUEEZE removed two disordered methanol molecules per formula unit.
;

_vrf_PLAT601_squeeze             
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of . 292 Ang3
RESPONSE: This is caused by the omission of two disordered 
methanol molecules by SQUEEZE.
;

# end Validation Reply Form

