# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_mo_20171213YKD_ZB_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc1yt9pr
_database_code_depnum_ccdc_archive 'CCDC 1811785'
_audit_update_record             
;
2017-12-16 deposited with the CCDC.
2018-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H25 O2 P'
_chemical_formula_weight         484.50

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   11.149(2)
_cell_length_b                   11.921(2)
_cell_length_c                   18.456(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2452.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4903
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      25.42
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.142
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14706
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.034
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_full        25.010
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4296
_reflns_number_gt                3943
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.984

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0841P)²+0.7332P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1557 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.42(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4296
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1252
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7208(3) 0.5130(3) 0.5202(2) 0.0291(7) Uani 1 1 d . . . . .
C2 C 0.6387(4) 0.5120(3) 0.4630(2) 0.0362(9) Uani 1 1 d . . . . .
H2 H 0.565675 0.548793 0.468250 0.043 Uiso 1 1 calc R U . . .
C3 C 0.6637(5) 0.4576(4) 0.3990(2) 0.0466(11) Uani 1 1 d . . . . .
H3 H 0.607154 0.456509 0.361918 0.056 Uiso 1 1 calc R U . . .
C4 C 0.7735(5) 0.4042(3) 0.3898(3) 0.0477(11) Uani 1 1 d . . . . .
H4 H 0.792792 0.371088 0.345685 0.057 Uiso 1 1 calc R U . . .
C5 C 0.8529(4) 0.4007(4) 0.4461(3) 0.0452(11) Uani 1 1 d . . . . .
H5 H 0.925615 0.363590 0.439935 0.054 Uiso 1 1 calc R U . . .
C6 C 0.8277(3) 0.4519(3) 0.5134(2) 0.0328(8) Uani 1 1 d . . . . .
C7 C 0.9080(3) 0.4394(3) 0.5765(2) 0.0349(9) Uani 1 1 d . . . . .
C8 C 1.0008(4) 0.3600(4) 0.5777(3) 0.0534(12) Uani 1 1 d . . . . .
H8 H 1.013950 0.315258 0.537200 0.064 Uiso 1 1 calc R U . . .
C9 C 1.0729(4) 0.3471(4) 0.6379(4) 0.0652(16) Uani 1 1 d . . . . .
H9 H 1.133695 0.293625 0.637458 0.078 Uiso 1 1 calc R U . . .
C10 C 1.0561(4) 0.4117(4) 0.6979(3) 0.0547(14) Uani 1 1 d . . . . .
H10 H 1.105297 0.402574 0.738208 0.066 Uiso 1 1 calc R U . . .
C11 C 0.9655(3) 0.4909(4) 0.6987(2) 0.0415(10) Uani 1 1 d . . . . .
H11 H 0.954200 0.535506 0.739418 0.050 Uiso 1 1 calc R U . . .
C12 C 0.8912(3) 0.5041(3) 0.6388(2) 0.0313(8) Uani 1 1 d . . . . .
C13 C 0.7933(3) 0.5873(3) 0.6434(2) 0.0306(8) Uani 1 1 d . . . . .
C14 C 0.6899(3) 0.5797(3) 0.58807(19) 0.0285(8) Uani 1 1 d . . . . .
C15 C 0.5858(3) 0.5236(4) 0.6298(2) 0.0349(9) Uani 1 1 d . . . . .
C16 C 0.5627(4) 0.4104(4) 0.6220(2) 0.0496(12) Uani 1 1 d . . . . .
H16 H 0.608855 0.368318 0.590002 0.059 Uiso 1 1 calc R U . . .
C17 C 0.4720(5) 0.3582(6) 0.6611(3) 0.0662(17) Uani 1 1 d . . . . .
H17 H 0.458507 0.281755 0.655308 0.079 Uiso 1 1 calc R U . . .
C18 C 0.4021(4) 0.4189(6) 0.7081(3) 0.0702(19) Uani 1 1 d . . . . .
H18 H 0.339581 0.384818 0.733174 0.084 Uiso 1 1 calc R U . . .
C19 C 0.4269(5) 0.5324(6) 0.7176(4) 0.090(2) Uani 1 1 d . . . . .
H19 H 0.381561 0.574160 0.750205 0.108 Uiso 1 1 calc R U . . .
C20 C 0.5174(5) 0.5833(5) 0.6794(3) 0.0663(17) Uani 1 1 d . . . . .
H20 H 0.533078 0.659011 0.686849 0.080 Uiso 1 1 calc R U . . .
C21 C 0.6595(3) 0.7027(3) 0.5665(2) 0.0279(8) Uani 1 1 d . . . . .
H21A H 0.643501 0.746195 0.609873 0.033 Uiso 1 1 calc R U . . .
H21B H 0.587789 0.703454 0.536781 0.033 Uiso 1 1 calc R U . . .
C22 C 0.8422(3) 0.6908(3) 0.3809(2) 0.0334(9) Uani 1 1 d . . . . .
H22 H 0.912099 0.665848 0.403192 0.040 Uiso 1 1 calc R U . . .
C23 C 0.8232(4) 0.6692(3) 0.3081(2) 0.0398(10) Uani 1 1 d . . . . .
H23 H 0.880463 0.630188 0.281439 0.048 Uiso 1 1 calc R U . . .
C24 C 0.7191(4) 0.7057(3) 0.2751(2) 0.0407(9) Uani 1 1 d . . . . .
H24 H 0.706595 0.691730 0.226143 0.049 Uiso 1 1 calc R U . . .
C25 C 0.6331(4) 0.7630(3) 0.3147(2) 0.0372(9) Uani 1 1 d . . . . .
H25 H 0.562701 0.786225 0.292231 0.045 Uiso 1 1 calc R U . . .
C26 C 0.6514(3) 0.7858(3) 0.3873(2) 0.0299(8) Uani 1 1 d . . . . .
H26 H 0.593795 0.824748 0.413667 0.036 Uiso 1 1 calc R U . . .
C27 C 0.7571(3) 0.7499(3) 0.42084(19) 0.0262(7) Uani 1 1 d . . . . .
C28 C 0.7764(4) 0.9139(3) 0.53761(19) 0.0343(8) Uani 1 1 d . . . . .
C29 C 0.7767(5) 0.9976(3) 0.4883(2) 0.0501(11) Uani 1 1 d . . . . .
H29 H 0.771194 0.980023 0.439365 0.060 Uiso 1 1 calc R U . . .
C30 C 0.7851(6) 1.1087(4) 0.5089(3) 0.0591(13) Uani 1 1 d . . . . .
H30 H 0.787395 1.164540 0.473815 0.071 Uiso 1 1 calc R U . . .
C31 C 0.7900(5) 1.1364(4) 0.5792(3) 0.0587(13) Uani 1 1 d . . . . .
H31 H 0.781937 1.210801 0.593499 0.070 Uiso 1 1 calc R U . . .
C32 C 0.8074(6) 1.0514(4) 0.6309(3) 0.0674(15) Uani 1 1 d . . . . .
H32 H 0.823069 1.069815 0.678942 0.081 Uiso 1 1 calc R U . . .
C33 C 0.8012(5) 0.9407(4) 0.6098(3) 0.0575(13) Uani 1 1 d . . . . .
H33 H 0.813470 0.883953 0.643591 0.069 Uiso 1 1 calc R U . . .
O1 O 0.9013(2) 0.7175(2) 0.53805(15) 0.0367(6) Uani 1 1 d . . . . .
O2 O 0.7887(3) 0.6557(3) 0.69240(14) 0.0456(7) Uani 1 1 d . . . . .
P1 P 0.78379(8) 0.76654(8) 0.51638(5) 0.0274(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.398(5) . ?
C1 C6 1.403(5) . ?
C1 C14 1.523(5) . ?
C2 C3 1.376(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.477(6) . ?
C7 C12 1.397(6) . ?
C7 C8 1.402(6) . ?
C8 C9 1.380(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.363(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.477(5) . ?
C13 O2 1.218(5) . ?
C13 C14 1.543(5) . ?
C14 C15 1.545(5) . ?
C14 C21 1.556(5) . ?
C15 C16 1.381(7) . ?
C15 C20 1.388(7) . ?
C16 C17 1.390(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.392(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.373(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 P1 1.832(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.384(6) . ?
C22 C27 1.393(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.381(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.384(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.398(5) . ?
C26 H26 0.9300 . ?
C27 P1 1.799(4) . ?
C28 C29 1.350(6) . ?
C28 C33 1.398(6) . ?
C28 P1 1.802(4) . ?
C29 C30 1.381(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.338(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.405(8) . ?
C31 H31 0.9300 . ?
C32 C33 1.377(7) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
O1 P1 1.489(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
C2 C1 C6 119.0(4) . . ?
C2 C1 C14 118.6(3) . . ?
C6 C1 C14 122.5(3) . . ?
C3 C2 C1 121.4(4) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.8(4) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 118.2(4) . . ?
C1 C6 C7 119.8(4) . . ?
C5 C6 C7 122.0(4) . . ?
C12 C7 C8 117.3(4) . . ?
C12 C7 C6 120.8(3) . . ?
C8 C7 C6 121.8(4) . . ?
C9 C8 C7 121.2(5) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 120.7(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.6(4) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.4(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.8(4) . . ?
C11 C12 C13 118.1(4) . . ?
C7 C12 C13 121.1(3) . . ?
O2 C13 C12 121.6(3) . . ?
O2 C13 C14 119.9(3) . . ?
C12 C13 C14 118.3(3) . . ?
C1 C14 C13 114.0(3) . . ?
C1 C14 C15 110.7(3) . . ?
C13 C14 C15 104.9(3) . . ?
C1 C14 C21 109.3(3) . . ?
C13 C14 C21 106.1(3) . . ?
C15 C14 C21 111.8(3) . . ?
C16 C15 C20 117.8(4) . . ?
C16 C15 C14 120.7(4) . . ?
C20 C15 C14 121.3(4) . . ?
C15 C16 C17 121.3(5) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 120.4(6) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 118.6(5) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C20 C19 C18 120.7(6) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C15 121.1(6) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
C14 C21 P1 110.8(2) . . ?
C14 C21 H21A 109.5 . . ?
P1 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
P1 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C23 C22 C27 120.2(4) . . ?
C23 C22 H22 119.9 . . ?
C27 C22 H22 119.9 . . ?
C24 C23 C22 119.8(4) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 120.4(4) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.4(4) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C27 119.5(4) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C22 C27 C26 119.6(3) . . ?
C22 C27 P1 117.5(3) . . ?
C26 C27 P1 122.7(3) . . ?
C29 C28 C33 118.2(4) . . ?
C29 C28 P1 125.0(3) . . ?
C33 C28 P1 114.9(3) . . ?
C28 C29 C30 121.6(4) . . ?
C28 C29 H29 119.2 . . ?
C30 C29 H29 119.2 . . ?
C31 C30 C29 120.4(4) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C32 119.0(4) . . ?
C30 C31 H31 120.5 . . ?
C32 C31 H31 120.5 . . ?
C33 C32 C31 119.5(5) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C32 C33 C28 119.9(5) . . ?
C32 C33 H33 120.1 . . ?
C28 C33 H33 120.1 . . ?
O1 P1 C27 111.44(16) . . ?
O1 P1 C28 111.36(18) . . ?
C27 P1 C28 108.23(16) . . ?
O1 P1 C21 111.51(16) . . ?
C27 P1 C21 108.92(16) . . ?
C28 P1 C21 105.12(18) . . ?

_refine_diff_density_max         0.665
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.053

