data_global
_audit_creation_method                  'APEX3 v2016.9-0'

_publ_requested_journal                 ?

_publ_contact_author_name               ?
_publ_contact_author_address            
;
;
_publ_contact_author_email              ?
_publ_contact_author_fax                ?
_publ_contact_author_phone              ?

_publ_section_title                     
;
;
_publ_section_abstract                  
;
;
_publ_section_references                
;
;
_publ_section_comment                   
;
;

data_yoshi60m
_chemical_name_systematic               ?
_chemical_name_common                   ?
_chemical_formula_moiety                ?
_chemical_formula_sum                   'C36 H37 O3 P'
_chemical_formula_iupac                 ?
_chemical_formula_weight                548.62

_chemical_melting_point                 ?

_space_group_crystal_system             monoclinic
_space_group_name_H-M_alt               'P 1 21/n 1'
_space_group_name_Hall                  '-P 2yn'
loop_
    _space_group_symop_operation_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                          7.5972(2)
_cell_length_b                          23.8844(6)
_cell_length_c                          15.6911(3)
_cell_angle_alpha                       90
_cell_angle_beta                        90.8293(10)
_cell_angle_gamma                       90
_cell_volume                            2846.92(12)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           7947
_cell_measurement_theta_min             2.5964
_cell_measurement_theta_max             28.2027
_cell_measurement_temperature           100.(2)

_exptl_crystal_description              block
_exptl_crystal_colour                   yellow
_exptl_crystal_size_max                 0.221
_exptl_crystal_size_mid                 0.190
_exptl_crystal_size_min                 0.154
_exptl_crystal_density_diffrn           1.280
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    1168

_exptl_absorpt_coefficient_mu           0.133
_exptl_absorpt_correction_type          'Numerical Mu Calculated'
_exptl_absorpt_process_details          
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min         0.87
_exptl_absorpt_correction_T_max         0.98

_exptl_special_details                  
;
; 

_diffrn_ambient_temperature             100.(2)

_diffrn_source                          'Incoatec microfocus source'
_diffrn_source_type                     'Bruker D8 Quest'

_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_monochromator         'Multilayer Mirror'

_diffrn_measurement_device_type         'Photon II CPADs detector'
_diffrn_measurement_method              'phi and omega scans'

_diffrn_detector_area_resol_mean        7.4074

_diffrn_reflns_number                   36188
_diffrn_reflns_av_R_equivalents         0.0725
_diffrn_reflns_av_unetI/netI            0.0599
_diffrn_reflns_theta_min                2.73
_diffrn_reflns_theta_max                28.29
_diffrn_reflns_theta_full               28.29
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full    0.995
_diffrn_reflns_limit_h_min              -10
_diffrn_reflns_limit_h_max              9
_diffrn_reflns_limit_k_min              -31
_diffrn_reflns_limit_k_max              31
_diffrn_reflns_limit_l_min              -20
_diffrn_reflns_limit_l_max              20

_refine_special_details                 
;
;

_reflns_number_total                    7026
_reflns_number_gt                       5336
_reflns_threshold_expression            'I > 2σ(I)'

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0788
_refine_ls_R_factor_gt                  0.0521
_refine_ls_wR_factor_gt                 0.1011
_refine_ls_wR_factor_ref                0.1137
_refine_ls_goodness_of_fit_ref          1.075
_refine_ls_restrained_S_all             1.075
_refine_ls_number_reflns                7026
_refine_ls_number_parameters            365
_refine_ls_number_restraints            0
_refine_ls_number_constraints           ?
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
    'w=1/[σ²(Fo²)+(0.0324P)²+1.9886P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            ?
_atom_sites_solution_secondary          ?

_refine_ls_shift/su_max                 0.000
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.435
_refine_diff_density_min                -0.372
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?

loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0033 0.0016 'International Tables 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'

_computing_data_collection              'APEX3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement              'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction               'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution           'XS, VERSION 2013/1'
_computing_structure_refinement         'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics           'XP (Bruker AXS Inc., 2016)'
_computing_publication_material         'APEX3 (Bruker AXS Inc., 2016)'

loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags_adp
    _atom_site_refinement_flags_occupancy
    _atom_site_refinement_flags_posn
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.5817(2) 0.19683(7) 0.23245(11) 0.0132(4) Uani d . . . 1 . .
    C C2 0.5374(2) 0.17979(7) 0.31094(11) 0.0126(4) Uani d . . . 1 . .
    C C3 0.5589(2) 0.22295(7) 0.37861(11) 0.0122(4) Uani d . . . 1 . .
    C C4 0.5176(2) 0.21401(8) 0.46366(11) 0.0147(4) Uani d . . . 1 . .
    H H4 0.4744 0.1786 0.4814 0.018 Uiso calc U . R 1 . .
    C C5 0.5394(2) 0.25649(7) 0.52191(11) 0.0143(4) Uani d . . . 1 . .
    H H5 0.511 0.2499 0.5798 0.017 Uiso calc U . R 1 . .
    C C6 0.6025(2) 0.30940(7) 0.49816(11) 0.0123(3) Uani d . . . 1 . .
    C C7 0.6156(2) 0.35401(7) 0.56217(11) 0.0135(4) Uani d . . . 1 . .
    C C8 0.5838(2) 0.34327(8) 0.64955(11) 0.0151(4) Uani d . . . 1 . .
    H H8 0.5608 0.306 0.6674 0.018 Uiso calc U . R 1 . .
    C C9 0.5854(2) 0.38552(8) 0.70873(11) 0.0152(4) Uani d . . . 1 . .
    C C10 0.6159(3) 0.44138(8) 0.68234(11) 0.0170(4) Uani d . . . 1 . .
    C C11 0.6518(3) 0.45207(8) 0.59852(11) 0.0163(4) Uani d . . . 1 . .
    H H11 0.6749 0.4895 0.5813 0.02 Uiso calc U . R 1 . .
    C C12 0.6552(2) 0.40873(7) 0.53715(11) 0.0146(4) Uani d . . . 1 . .
    C C13 0.7087(2) 0.41969(7) 0.44962(11) 0.0148(4) Uani d . . . 1 . .
    C C14 0.7679(3) 0.47317(8) 0.42475(12) 0.0208(4) Uani d . . . 1 . .
    H H14 0.7608 0.5033 0.464 0.025 Uiso calc U . R 1 . .
    C C15 0.8357(3) 0.48291(8) 0.34529(12) 0.0228(4) Uani d . . . 1 . .
    H H15 0.8729 0.5194 0.3297 0.027 Uiso calc U . R 1 . .
    C C16 0.8492(3) 0.43869(8) 0.28807(12) 0.0202(4) Uani d . . . 1 . .
    H H16 0.8996 0.4447 0.2338 0.024 Uiso calc U . R 1 . .
    C C17 0.7898(2) 0.38632(8) 0.31002(11) 0.0155(4) Uani d . . . 1 . .
    H H17 0.8001 0.3566 0.2702 0.019 Uiso calc U . R 1 . .
    C C18 0.7142(2) 0.37535(7) 0.38956(11) 0.0135(4) Uani d . . . 1 . .
    C C19 0.6477(2) 0.31958(7) 0.41168(11) 0.0118(3) Uani d . . . 1 . .
    C C20 0.6247(2) 0.27482(7) 0.35230(10) 0.0118(3) Uani d . . . 1 . .
    C C21 0.5002(2) 0.31167(7) 0.18225(10) 0.0132(4) Uani d . . . 1 . .
    C C22 0.3220(2) 0.31045(7) 0.20206(11) 0.0149(4) Uani d . . . 1 . .
    H H22 0.2821 0.2866 0.2463 0.018 Uiso calc U . R 1 . .
    C C23 0.2028(3) 0.34372(8) 0.15777(11) 0.0167(4) Uani d . . . 1 . .
    H H23 0.0816 0.3429 0.1718 0.02 Uiso calc U . R 1 . .
    C C24 0.2608(3) 0.37835(8) 0.09272(11) 0.0180(4) Uani d . . . 1 . .
    H H24 0.1792 0.4014 0.0627 0.022 Uiso calc U . R 1 . .
    C C25 0.4373(3) 0.37929(8) 0.07157(11) 0.0192(4) Uani d . . . 1 . .
    H H25 0.4763 0.4026 0.0266 0.023 Uiso calc U . R 1 . .
    C C26 0.5571(3) 0.34605(8) 0.11629(11) 0.0167(4) Uani d . . . 1 . .
    H H26 0.6781 0.3467 0.1019 0.02 Uiso calc U . R 1 . .
    C C27 0.5909(3) 0.16020(8) 0.15429(11) 0.0161(4) Uani d . . . 1 . .
    H H27A 0.4878 0.1349 0.1541 0.019 Uiso calc U . R 1 . .
    H H27B 0.6975 0.1365 0.1595 0.019 Uiso calc U . R 1 . .
    C C28 0.5954(3) 0.19008(8) 0.06841(11) 0.0169(4) Uani d . . . 1 . .
    H H28A 0.6876 0.2194 0.07 0.02 Uiso calc U . R 1 . .
    H H28B 0.4807 0.2086 0.0573 0.02 Uiso calc U . R 1 . .
    C C29 0.6334(3) 0.14895(8) -0.00342(11) 0.0196(4) Uani d . . . 1 . .
    H H29A 0.7452 0.1292 0.0094 0.024 Uiso calc U . R 1 . .
    H H29B 0.5383 0.1206 -0.0062 0.024 Uiso calc U . R 1 . .
    C C30 0.6468(3) 0.17778(9) -0.08975(11) 0.0251(5) Uani d . . . 1 . .
    H H30A 0.5351 0.1964 -0.1036 0.038 Uiso calc U . R 1 . .
    H H30B 0.6724 0.1499 -0.1336 0.038 Uiso calc U . R 1 . .
    H H30C 0.7416 0.2056 -0.0875 0.038 Uiso calc U . R 1 . .
    C C31 0.4854(2) 0.12107(7) 0.33338(11) 0.0141(4) Uani d . . . 1 . .
    H H31A 0.4297 0.103 0.283 0.017 Uiso calc U . R 1 . .
    H H31B 0.3979 0.122 0.3795 0.017 Uiso calc U . R 1 . .
    C C32 0.6453(2) 0.08655(7) 0.36260(11) 0.0153(4) Uani d . . . 1 . .
    H H32A 0.7241 0.0808 0.3137 0.018 Uiso calc U . R 1 . .
    H H32B 0.7117 0.1077 0.4068 0.018 Uiso calc U . R 1 . .
    C C33 0.5925(3) 0.03006(8) 0.39841(12) 0.0200(4) Uani d . . . 1 . .
    H H33A 0.5183 0.0102 0.3557 0.024 Uiso calc U . R 1 . .
    H H33B 0.5211 0.036 0.4499 0.024 Uiso calc U . R 1 . .
    C C34 0.7507(3) -0.00655(9) 0.42163(14) 0.0276(5) Uani d . . . 1 . .
    H H34A 0.8284 -0.0094 0.3725 0.041 Uiso calc U . R 1 . .
    H H34B 0.71 -0.044 0.4376 0.041 Uiso calc U . R 1 . .
    H H34C 0.8153 0.0102 0.4697 0.041 Uiso calc U . R 1 . .
    C C35 0.5511(3) 0.32330(8) 0.82624(12) 0.0203(4) Uani d . . . 1 . .
    H H35A 0.4523 0.3034 0.7993 0.03 Uiso calc U . R 1 . .
    H H35B 0.535 0.3243 0.8881 0.03 Uiso calc U . R 1 . .
    H H35C 0.6614 0.3039 0.8135 0.03 Uiso calc U . R 1 . .
    C C36 0.6352(3) 0.53749(8) 0.72013(13) 0.0250(5) Uani d . . . 1 . .
    H H36A 0.7552 0.5419 0.699 0.038 Uiso calc U . R 1 . .
    H H36B 0.6183 0.5621 0.7693 0.038 Uiso calc U . R 1 . .
    H H36C 0.5505 0.5474 0.6749 0.038 Uiso calc U . R 1 . .
    O O1 0.84011(17) 0.27614(5) 0.20393(8) 0.0156(3) Uani d . . . 1 . .
    O O2 0.55811(18) 0.37921(5) 0.79401(8) 0.0190(3) Uani d . . . 1 . .
    O O3 0.60813(19) 0.48057(5) 0.74520(8) 0.0228(3) Uani d . . . 1 . .
    P P1 0.65873(6) 0.26798(2) 0.23732(3) 0.01201(11) Uani d . . . 1 . .


_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . 1.345(2) ?
    C1 C27 . 1.509(2) ?
    C1 P1 . 1.7984(18) ?
    C2 C3 . 1.487(2) ?
    C2 C31 . 1.500(2) ?
    C3 C4 . 1.392(2) ?
    C3 C20 . 1.400(2) ?
    C4 C5 . 1.374(2) ?
    C5 C6 . 1.404(2) ?
    C6 C19 . 1.425(2) ?
    C6 C7 . 1.467(2) ?
    C7 C12 . 1.399(3) ?
    C7 C8 . 1.419(2) ?
    C8 C9 . 1.371(2) ?
    C9 O2 . 1.365(2) ?
    C9 C10 . 1.417(3) ?
    C10 O3 . 1.362(2) ?
    C10 C11 . 1.371(3) ?
    C11 C12 . 1.414(2) ?
    C12 C13 . 1.461(2) ?
    C13 C14 . 1.411(3) ?
    C13 C18 . 1.419(2) ?
    C14 C15 . 1.376(3) ?
    C15 C16 . 1.391(3) ?
    C16 C17 . 1.375(3) ?
    C17 C18 . 1.406(2) ?
    C18 C19 . 1.468(2) ?
    C19 C20 . 1.427(2) ?
    C20 P1 . 1.8336(17) ?
    C21 C22 . 1.393(3) ?
    C21 C26 . 1.395(2) ?
    C21 P1 . 1.8046(18) ?
    C22 C23 . 1.384(3) ?
    C23 C24 . 1.390(3) ?
    C24 C25 . 1.386(3) ?
    C25 C26 . 1.390(3) ?
    C27 C28 . 1.526(2) ?
    C28 C29 . 1.526(3) ?
    C29 C30 . 1.524(3) ?
    C31 C32 . 1.533(2) ?
    C32 C33 . 1.518(2) ?
    C33 C34 . 1.526(3) ?
    C35 O2 . 1.429(2) ?
    C36 O3 . 1.431(2) ?
    O1 P1 . 1.4941(14) ?

loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 C27 . . 125.73(16) ?
    C2 C1 P1 . . 109.43(13) ?
    C27 C1 P1 . . 124.31(13) ?
    C1 C2 C3 . . 114.70(16) ?
    C1 C2 C31 . . 124.63(16) ?
    C3 C2 C31 . . 120.45(15) ?
    C4 C3 C20 . . 120.32(16) ?
    C4 C3 C2 . . 123.66(16) ?
    C20 C3 C2 . . 116.01(15) ?
    C5 C4 C3 . . 119.85(17) ?
    C4 C5 C6 . . 121.77(16) ?
    C5 C6 C19 . . 119.61(15) ?
    C5 C6 C7 . . 119.49(16) ?
    C19 C6 C7 . . 120.87(16) ?
    C12 C7 C8 . . 118.72(16) ?
    C12 C7 C6 . . 119.96(16) ?
    C8 C7 C6 . . 121.29(16) ?
    C9 C8 C7 . . 121.42(17) ?
    O2 C9 C8 . . 125.62(17) ?
    O2 C9 C10 . . 114.72(15) ?
    C8 C9 C10 . . 119.66(16) ?
    O3 C10 C11 . . 125.31(17) ?
    O3 C10 C9 . . 115.25(16) ?
    C11 C10 C9 . . 119.43(16) ?
    C10 C11 C12 . . 121.51(17) ?
    C7 C12 C11 . . 119.12(16) ?
    C7 C12 C13 . . 119.67(16) ?
    C11 C12 C13 . . 121.13(16) ?
    C14 C13 C18 . . 118.63(17) ?
    C14 C13 C12 . . 121.07(16) ?
    C18 C13 C12 . . 120.13(16) ?
    C15 C14 C13 . . 121.92(18) ?
    C14 C15 C16 . . 119.26(18) ?
    C17 C16 C15 . . 120.08(18) ?
    C16 C17 C18 . . 122.11(17) ?
    C17 C18 C13 . . 117.85(16) ?
    C17 C18 C19 . . 121.69(16) ?
    C13 C18 C19 . . 120.44(16) ?
    C6 C19 C20 . . 117.70(15) ?
    C6 C19 C18 . . 117.92(15) ?
    C20 C19 C18 . . 124.38(15) ?
    C3 C20 C19 . . 120.73(15) ?
    C3 C20 P1 . . 105.51(12) ?
    C19 C20 P1 . . 133.74(13) ?
    C22 C21 C26 . . 119.37(16) ?
    C22 C21 P1 . . 121.65(13) ?
    C26 C21 P1 . . 118.94(14) ?
    C23 C22 C21 . . 120.44(17) ?
    C22 C23 C24 . . 119.87(18) ?
    C25 C24 C23 . . 120.22(17) ?
    C24 C25 C26 . . 119.90(17) ?
    C25 C26 C21 . . 120.20(18) ?
    C1 C27 C28 . . 116.65(15) ?
    C27 C28 C29 . . 111.00(15) ?
    C30 C29 C28 . . 112.43(17) ?
    C2 C31 C32 . . 111.25(15) ?
    C33 C32 C31 . . 112.11(15) ?
    C32 C33 C34 . . 112.73(17) ?
    C9 O2 C35 . . 117.18(14) ?
    C10 O3 C36 . . 116.49(15) ?
    O1 P1 C1 . . 114.18(8) ?
    O1 P1 C21 . . 111.66(8) ?
    C1 P1 C21 . . 108.15(8) ?
    O1 P1 C20 . . 118.52(8) ?
    C1 P1 C20 . . 94.33(8) ?
    C21 P1 C20 . . 108.48(8) ?



