# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_112
_database_code_depnum_ccdc_archive 'CCDC 1874220'
loop_
_audit_author_name
_audit_author_address
'Ruwei Shen'
;Nanjing Tech University
China
;
_audit_update_record             
;
2018-10-19 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H21 O2 P1'
_chemical_formula_sum            'C27 H21 O2 P1'
_chemical_formula_weight         408.41

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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.430(3)
_cell_length_b                   8.5473(14)
_cell_length_c                   20.666(3)
_cell_angle_alpha                90
_cell_angle_beta                 127.448(9)
_cell_angle_gamma                90
_cell_volume                     2163.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2625
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      25.00

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.148
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15509
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.662
_diffrn_reflns_theta_max         26.946
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4500
_reflns_number_gt                2876
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1196P)²+0.9256P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4300
_refine_ls_number_parameters     272
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.2242
_refine_ls_wR_factor_gt          0.1966
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.010
_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_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
P1 P 0.20493(6) 0.12436(9) 0.15392(4) 0.0552(3) Uani 1 1 d . . . . .
O1 O 0.18876(17) 0.0415(3) 0.08442(13) 0.0642(6) Uani 1 1 d . . . . .
O2 O -0.02742(17) 0.0741(3) 0.05581(12) 0.0668(6) Uani 1 1 d . . . . .
H2B H -0.0793 0.0187 0.0221 0.100 Uiso 1 1 d R U . . .
C1 C 0.1687(2) 0.3280(4) 0.13277(19) 0.0592(7) Uani 1 1 d . . . . .
C2 C 0.1508(3) 0.4176(4) 0.1796(2) 0.0805(10) Uani 1 1 d . . . . .
H2A H 0.1553 0.3721 0.2225 0.097 Uiso 1 1 calc R U . . .
C3 C 0.1261(4) 0.5749(5) 0.1623(3) 0.0948(13) Uani 1 1 d . . . . .
H3A H 0.1140 0.6352 0.1936 0.114 Uiso 1 1 calc R U . . .
C4 C 0.1195(4) 0.6420(5) 0.0992(3) 0.0925(12) Uani 1 1 d . . . . .
H4A H 0.1028 0.7477 0.0877 0.111 Uiso 1 1 calc R U . . .
C5 C 0.1371(3) 0.5561(5) 0.0541(3) 0.0844(11) Uani 1 1 d . . . . .
H5A H 0.1326 0.6026 0.0115 0.101 Uiso 1 1 calc R U . . .
C6 C 0.1619(3) 0.3991(4) 0.0702(2) 0.0699(9) Uani 1 1 d . . . . .
H6A H 0.1741 0.3409 0.0385 0.084 Uiso 1 1 calc R U . . .
C7 C 0.3478(3) 0.1168(4) 0.2395(2) 0.0654(8) Uani 1 1 d . . . . .
C8 C 0.4007(3) 0.2242(6) 0.3002(2) 0.1002(14) Uani 1 1 d . . . . .
H8A H 0.3617 0.3072 0.3002 0.120 Uiso 1 1 calc R U . . .
C9 C 0.5112(4) 0.2127(8) 0.3620(3) 0.1254(18) Uani 1 1 d . . . . .
H9A H 0.5452 0.2876 0.4030 0.150 Uiso 1 1 calc R U . . .
C10 C 0.5704(4) 0.0966(9) 0.3641(3) 0.126(2) Uani 1 1 d . . . . .
H10A H 0.6454 0.0924 0.4049 0.151 Uiso 1 1 calc R U . . .
C11 C 0.5194(4) -0.0154(9) 0.3055(4) 0.137(2) Uani 1 1 d . . . . .
H11A H 0.5595 -0.0987 0.3072 0.165 Uiso 1 1 calc R U . . .
C12 C 0.4087(3) -0.0072(6) 0.2435(3) 0.1075(15) Uani 1 1 d . . . . .
H12A H 0.3747 -0.0854 0.2042 0.129 Uiso 1 1 calc R U . . .
C13 C 0.1318(2) 0.0414(3) 0.18878(18) 0.0574(7) Uani 1 1 d . . . . .
C14 C 0.0201(2) 0.0167(3) 0.13103(18) 0.0572(7) Uani 1 1 d . . . . .
C15 C -0.0373(3) -0.0639(4) 0.1540(2) 0.0647(8) Uani 1 1 d . . . . .
C16 C 0.0188(3) -0.1073(4) 0.2353(2) 0.0763(10) Uani 1 1 d . . . . .
H16A H -0.0191 -0.1601 0.2504 0.092 Uiso 1 1 calc R U . . .
C17 C 0.1273(3) -0.0758(5) 0.2941(2) 0.0792(10) Uani 1 1 d . . . . .
C18 C 0.1833(3) -0.0021(4) 0.26920(19) 0.0676(8) Uani 1 1 d . . . . .
H18A H 0.2574 0.0185 0.3077 0.081 Uiso 1 1 calc R U . . .
C19 C 0.1836(4) -0.1190(7) 0.3821(3) 0.1182(18) Uani 1 1 d . . . . .
H19A H 0.2267 -0.0322 0.4164 0.177 Uiso 1 1 calc R U . . .
H19B H 0.2301 -0.2078 0.3960 0.177 Uiso 1 1 calc R U . . .
H19C H 0.1298 -0.1446 0.3898 0.177 Uiso 1 1 calc R U . . .
C20 C -0.1510(3) -0.0983(4) 0.0964(2) 0.0732(9) Uani 1 1 d . . . . .
C21 C -0.2454(3) -0.1285(5) 0.0503(2) 0.0811(10) Uani 1 1 d . . . . .
C22 C -0.3601(3) -0.1575(5) -0.0063(3) 0.0861(11) Uani 1 1 d . U . . .
C23 C -0.4127(5) -0.2483(8) 0.0135(4) 0.156(2) Uani 1 1 d . U . . .
H23A H -0.3746 -0.2961 0.0643 0.187 Uiso 1 1 calc R U . . .
C24 C -0.5268(6) -0.2690(10) -0.0448(5) 0.171(3) Uani 1 1 d . U . . .
H24A H -0.5637 -0.3277 -0.0306 0.206 Uiso 1 1 calc R U . . .
C25 C -0.5826(4) -0.2079(8) -0.1184(4) 0.1294(19) Uani 1 1 d . U . . .
H25A H -0.6585 -0.2116 -0.1534 0.155 Uiso 1 1 calc R U . . .
C26 C -0.5279(4) -0.1410(8) -0.1413(4) 0.134(2) Uani 1 1 d . U . . .
H26A H -0.5647 -0.1091 -0.1951 0.160 Uiso 1 1 calc R U . . .
C27 C -0.4170(4) -0.1183(7) -0.0862(3) 0.1205(17) Uani 1 1 d . U . . .
H27A H -0.3798 -0.0748 -0.1042 0.145 Uiso 1 1 calc R U . . .


_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 1.480(2) . ?
P1 C1 1.799(3) . ?
P1 C7 1.803(3) . ?
P1 C13 1.812(3) . ?
O2 C14 1.345(3) . ?
O2 H2B 0.8200 . ?
C1 C6 1.374(5) . ?
C1 C2 1.387(5) . ?
C2 C3 1.384(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.370(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.338(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.379(5) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.356(5) . ?
C7 C12 1.385(5) . ?
C8 C9 1.378(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.331(8) . ?
C9 H9A 0.9300 . ?
C10 C11 1.357(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.380(6) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C18 1.388(4) . ?
C13 C14 1.392(4) . ?
C14 C15 1.414(4) . ?
C15 C16 1.393(5) . ?
C15 C20 1.429(5) . ?
C16 C17 1.370(5) . ?
C16 H16A 0.9300 . ?
C17 C18 1.396(5) . ?
C17 C19 1.508(5) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.187(5) . ?
C21 C22 1.429(5) . ?
C22 C23 1.354(6) . ?
C22 C27 1.359(6) . ?
C23 C24 1.416(8) . ?
C23 H23A 0.9300 . ?
C24 C25 1.318(8) . ?
C24 H24A 0.9300 . ?
C25 C26 1.323(7) . ?
C25 H25A 0.9300 . ?
C26 C27 1.376(7) . ?
C26 H26A 0.9300 . ?
C27 H27A 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
O1 P1 C1 112.54(14) . . ?
O1 P1 C7 108.61(14) . . ?
C1 P1 C7 106.70(15) . . ?
O1 P1 C13 114.85(13) . . ?
C1 P1 C13 107.34(14) . . ?
C7 P1 C13 106.33(14) . . ?
C14 O2 H2B 109.6 . . ?
C6 C1 C2 118.6(3) . . ?
C6 C1 P1 119.4(2) . . ?
C2 C1 P1 121.9(3) . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C1 C6 C5 120.6(3) . . ?
C1 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C8 C7 C12 117.2(4) . . ?
C8 C7 P1 125.0(3) . . ?
C12 C7 P1 117.8(3) . . ?
C7 C8 C9 121.2(5) . . ?
C7 C8 H8A 119.4 . . ?
C9 C8 H8A 119.4 . . ?
C10 C9 C8 121.5(5) . . ?
C10 C9 H9A 119.3 . . ?
C8 C9 H9A 119.3 . . ?
C9 C10 C11 118.8(5) . . ?
C9 C10 H10A 120.6 . . ?
C11 C10 H10A 120.6 . . ?
C10 C11 C12 120.7(5) . . ?
C10 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
C11 C12 C7 120.4(5) . . ?
C11 C12 H12A 119.8 . . ?
C7 C12 H12A 119.8 . . ?
C18 C13 C14 119.7(3) . . ?
C18 C13 P1 122.6(2) . . ?
C14 C13 P1 117.6(2) . . ?
O2 C14 C13 117.2(3) . . ?
O2 C14 C15 123.6(3) . . ?
C13 C14 C15 119.2(3) . . ?
C16 C15 C14 118.5(3) . . ?
C16 C15 C20 120.0(3) . . ?
C14 C15 C20 121.5(3) . . ?
C17 C16 C15 123.1(3) . . ?
C17 C16 H16A 118.5 . . ?
C15 C16 H16A 118.5 . . ?
C16 C17 C18 117.3(3) . . ?
C16 C17 C19 121.2(4) . . ?
C18 C17 C19 121.5(4) . . ?
C13 C18 C17 122.0(3) . . ?
C13 C18 H18A 119.0 . . ?
C17 C18 H18A 119.0 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C15 178.0(4) . . ?
C20 C21 C22 177.4(5) . . ?
C23 C22 C27 116.5(5) . . ?
C23 C22 C21 121.5(4) . . ?
C27 C22 C21 121.0(4) . . ?
C22 C23 C24 118.6(6) . . ?
C22 C23 H23A 120.7 . . ?
C24 C23 H23A 120.7 . . ?
C25 C24 C23 122.3(6) . . ?
C25 C24 H24A 118.8 . . ?
C23 C24 H24A 118.8 . . ?
C26 C25 C24 118.3(5) . . ?
C26 C25 H25A 120.9 . . ?
C24 C25 H25A 120.9 . . ?
C25 C26 C27 120.6(6) . . ?
C25 C26 H26A 119.7 . . ?
C27 C26 H26A 119.7 . . ?
C22 C27 C26 122.0(5) . . ?
C22 C27 H27A 119.0 . . ?
C26 C27 H27A 119.0 . . ?

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
O1 P1 C1 C6 -18.9(3) . . . . ?
C7 P1 C1 C6 100.1(3) . . . . ?
C13 P1 C1 C6 -146.2(3) . . . . ?
O1 P1 C1 C2 163.3(3) . . . . ?
C7 P1 C1 C2 -77.7(3) . . . . ?
C13 P1 C1 C2 36.0(3) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
P1 C1 C2 C3 178.1(3) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C3 C4 C5 C6 0.1(7) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
P1 C1 C6 C5 -178.2(3) . . . . ?
C4 C5 C6 C1 0.2(6) . . . . ?
O1 P1 C7 C8 152.7(3) . . . . ?
C1 P1 C7 C8 31.2(4) . . . . ?
C13 P1 C7 C8 -83.2(4) . . . . ?
O1 P1 C7 C12 -26.7(4) . . . . ?
C1 P1 C7 C12 -148.2(3) . . . . ?
C13 P1 C7 C12 97.4(3) . . . . ?
C12 C7 C8 C9 1.9(7) . . . . ?
P1 C7 C8 C9 -177.5(4) . . . . ?
C7 C8 C9 C10 0.6(9) . . . . ?
C8 C9 C10 C11 -2.4(10) . . . . ?
C9 C10 C11 C12 1.8(10) . . . . ?
C10 C11 C12 C7 0.7(9) . . . . ?
C8 C7 C12 C11 -2.5(7) . . . . ?
P1 C7 C12 C11 176.9(4) . . . . ?
O1 P1 C13 C18 125.4(3) . . . . ?
C1 P1 C13 C18 -108.6(3) . . . . ?
C7 P1 C13 C18 5.3(3) . . . . ?
O1 P1 C13 C14 -52.4(3) . . . . ?
C1 P1 C13 C14 73.5(3) . . . . ?
C7 P1 C13 C14 -172.6(2) . . . . ?
C18 C13 C14 O2 174.0(3) . . . . ?
P1 C13 C14 O2 -8.1(4) . . . . ?
C18 C13 C14 C15 -5.0(4) . . . . ?
P1 C13 C14 C15 172.9(2) . . . . ?
O2 C14 C15 C16 -175.0(3) . . . . ?
C13 C14 C15 C16 3.9(5) . . . . ?
O2 C14 C15 C20 3.8(5) . . . . ?
C13 C14 C15 C20 -177.3(3) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C20 C15 C16 C17 -178.9(4) . . . . ?
C15 C16 C17 C18 -2.6(6) . . . . ?
C15 C16 C17 C19 177.4(4) . . . . ?
C14 C13 C18 C17 2.3(5) . . . . ?
P1 C13 C18 C17 -175.5(3) . . . . ?
C16 C17 C18 C13 1.5(5) . . . . ?
C19 C17 C18 C13 -178.5(4) . . . . ?
C27 C22 C23 C24 -12.7(9) . . . . ?
C21 C22 C23 C24 178.4(6) . . . . ?
C22 C23 C24 C25 2.6(13) . . . . ?
C23 C24 C25 C26 8.1(13) . . . . ?
C24 C25 C26 C27 -8.2(11) . . . . ?
C23 C22 C27 C26 13.0(9) . . . . ?
C21 C22 C27 C26 -178.1(5) . . . . ?
C25 C26 C27 C22 -2.5(10) . . . . ?

_refine_diff_density_max         0.849
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1874221'
loop_
_audit_author_name
_audit_author_address
'Ruwei Shen'
;Nanjing Tech University
China
;
_audit_update_record             
;
2018-10-19 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H29 O2 P??CH4O'
_chemical_formula_sum            'C20 H33 O3 P'
_chemical_formula_weight         352.43

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.624(2)
_cell_length_b                   16.463(3)
_cell_length_c                   10.9887(18)
_cell_angle_alpha                90
_cell_angle_beta                 105.891(2)
_cell_angle_gamma                90
_cell_volume                     2022.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4252
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.04

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'multi-scan '
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'multi-scan '
_exptl_absorpt_special_details   '(SADABS; Sheldrick, 2003)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14080
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.822
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_full        25.003
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3548
_reflns_number_gt                2912
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0741P)²+0.5720P] 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_number_reflns         3548
_refine_ls_number_parameters     218
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1386
_refine_ls_wR_factor_gt          0.1318
_refine_ls_goodness_of_fit_ref   1.080
_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_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 0.63770(17) 0.30091(13) 0.49381(18) 0.0426(5) Uani 1 1 d . . . . .
C2 C 0.5506(2) 0.36026(14) 0.4613(2) 0.0527(6) Uani 1 1 d . . . . .
H2B H 0.5534 0.3991 0.4008 0.063 Uiso 1 1 calc R U . . .
C3 C 0.4586(2) 0.36141(16) 0.5199(2) 0.0584(6) Uani 1 1 d . . . . .
H3A H 0.4003 0.4015 0.4975 0.070 Uiso 1 1 calc R U . . .
C4 C 0.45105(18) 0.30489(15) 0.6104(2) 0.0537(6) Uani 1 1 d . . . . .
C5 C 0.53980(17) 0.24625(13) 0.6422(2) 0.0458(5) Uani 1 1 d . . . . .
H5A H 0.5368 0.2076 0.7030 0.055 Uiso 1 1 calc R U . . .
C6 C 0.63346(16) 0.24355(12) 0.58575(18) 0.0393(5) Uani 1 1 d . . . . .
C7 C 0.3518(2) 0.3064(2) 0.6755(3) 0.0790(8) Uani 1 1 d . . . . .
H7A H 0.3625 0.2623 0.7348 0.118 Uiso 1 1 calc R U . . .
H7B H 0.3540 0.3570 0.7196 0.118 Uiso 1 1 calc R U . . .
H7C H 0.2759 0.3009 0.6135 0.118 Uiso 1 1 calc R U . . .
C8 C 0.8925(2) 0.29613(14) 0.7410(2) 0.0534(6) Uani 1 1 d . . . . .
H8A H 0.8365 0.3317 0.6833 0.064 Uiso 1 1 calc R U . . .
H8B H 0.8657 0.2899 0.8167 0.064 Uiso 1 1 calc R U . . .
C9 C 1.0161(2) 0.33455(16) 0.7758(3) 0.0715(7) Uani 1 1 d . . . . .
H9A H 1.0397 0.3454 0.6993 0.086 Uiso 1 1 calc R U . . .
H9B H 1.0134 0.3859 0.8181 0.086 Uiso 1 1 calc R U . . .
C10 C 1.1080(2) 0.28000(18) 0.8614(3) 0.0754(8) Uani 1 1 d . . . . .
H10A H 1.1865 0.3046 0.8775 0.090 Uiso 1 1 calc R U . . .
H10B H 1.0894 0.2738 0.9417 0.090 Uiso 1 1 calc R U . . .
C11 C 1.1091(2) 0.19776(18) 0.8012(3) 0.0719(8) Uani 1 1 d . . . . .
H11A H 1.1657 0.1627 0.8592 0.086 Uiso 1 1 calc R U . . .
H11B H 1.1353 0.2036 0.7251 0.086 Uiso 1 1 calc R U . . .
C12 C 0.98540(19) 0.15861(15) 0.7679(2) 0.0587(6) Uani 1 1 d . . . . .
H12A H 0.9615 0.1491 0.8446 0.070 Uiso 1 1 calc R U . . .
H12B H 0.9883 0.1066 0.7274 0.070 Uiso 1 1 calc R U . . .
C13 C 0.89336(17) 0.21336(12) 0.67895(19) 0.0410(5) Uani 1 1 d . . . . .
H13A H 0.9192 0.2215 0.6021 0.049 Uiso 1 1 calc R U . . .
C14 C 0.73272(17) 0.10189(12) 0.49387(18) 0.0418(5) Uani 1 1 d . . . . .
H14A H 0.7479 0.1365 0.4273 0.050 Uiso 1 1 calc R U . . .
C15 C 0.8220(2) 0.03275(18) 0.5162(3) 0.0792(9) Uani 1 1 d . . . . .
H15A H 0.8133 0.0002 0.5868 0.095 Uiso 1 1 calc R U . . .
H15B H 0.9024 0.0549 0.5388 0.095 Uiso 1 1 calc R U . . .
C16 C 0.8050(3) -0.0211(2) 0.4004(3) 0.0909(10) Uani 1 1 d . . . . .
H16A H 0.8255 0.0094 0.3338 0.109 Uiso 1 1 calc R U . . .
H16B H 0.8593 -0.0670 0.4215 0.109 Uiso 1 1 calc R U . . .
C17 C 0.6795(2) -0.05203(17) 0.3523(3) 0.0737(8) Uani 1 1 d . . . . .
H17A H 0.6715 -0.0816 0.2741 0.088 Uiso 1 1 calc R U . . .
H17B H 0.6628 -0.0893 0.4137 0.088 Uiso 1 1 calc R U . . .
C18 C 0.5919(3) 0.0151(2) 0.3295(3) 0.0890(10) Uani 1 1 d . . . . .
H18A H 0.5117 -0.0074 0.3057 0.107 Uiso 1 1 calc R U . . .
H18B H 0.6013 0.0479 0.2595 0.107 Uiso 1 1 calc R U . . .
C19 C 0.6067(2) 0.06915(19) 0.4459(3) 0.0770(9) Uani 1 1 d . . . . .
H19A H 0.5511 0.1143 0.4246 0.092 Uiso 1 1 calc R U . . .
H19B H 0.5872 0.0381 0.5126 0.092 Uiso 1 1 calc R U . . .
C20 C 0.8446(5) 0.0086(3) 1.0086(6) 0.154(2) Uani 1 1 d . . . . .
H20A H 0.8898 -0.0335 1.0610 0.232 Uiso 1 1 calc R U . . .
H20B H 0.7780 0.0235 1.0398 0.232 Uiso 1 1 calc R U . . .
H20C H 0.8948 0.0551 1.0103 0.232 Uiso 1 1 calc R U . . .
O1 O 0.73109(13) 0.29566(9) 0.44172(14) 0.0515(4) Uani 1 1 d . . . . .
H1A H 0.7187 0.3254 0.3796 0.077 Uiso 1 1 calc R U . . .
O2 O 0.72239(12) 0.11711(8) 0.74055(12) 0.0440(4) Uani 1 1 d . . . . .
O3 O 0.8047(5) -0.0181(2) 0.8911(5) 0.221(2) Uani 1 1 d . U . . .
H3B H 0.7788 0.0202 0.8438 0.265 Uiso 1 1 calc R U . . .
P1 P 0.74534(4) 0.16535(3) 0.63275(5) 0.03651(18) 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 O1 1.362(2) . ?
C1 C2 1.382(3) . ?
C1 C6 1.394(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.382(3) . ?
C4 C5 1.386(3) . ?
C4 C7 1.515(3) . ?
C5 C6 1.394(3) . ?
C6 P1 1.802(2) . ?
C8 C9 1.520(3) . ?
C8 C13 1.525(3) . ?
C9 C10 1.510(4) . ?
C10 C11 1.508(4) . ?
C11 C12 1.526(3) . ?
C12 C13 1.529(3) . ?
C13 P1 1.8341(19) . ?
C14 C19 1.514(3) . ?
C14 C15 1.514(3) . ?
C14 P1 1.8220(19) . ?
C15 C16 1.520(3) . ?
C16 C17 1.498(4) . ?
C17 C18 1.477(4) . ?
C18 C19 1.529(3) . ?
C20 O3 1.322(6) . ?
O2 P1 1.5093(14) . ?

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 C1 C2 123.27(19) . . ?
O1 C1 C6 116.89(17) . . ?
C2 C1 C6 119.83(18) . . ?
C1 C2 C3 119.5(2) . . ?
C4 C3 C2 122.2(2) . . ?
C3 C4 C5 117.4(2) . . ?
C3 C4 C7 122.4(2) . . ?
C5 C4 C7 120.2(2) . . ?
C4 C5 C6 121.9(2) . . ?
C1 C6 C5 119.23(18) . . ?
C1 C6 P1 121.73(14) . . ?
C5 C6 P1 119.05(16) . . ?
C9 C8 C13 111.25(19) . . ?
C10 C9 C8 111.6(2) . . ?
C11 C10 C9 110.5(2) . . ?
C10 C11 C12 111.3(2) . . ?
C11 C12 C13 110.7(2) . . ?
C8 C13 C12 109.27(18) . . ?
C8 C13 P1 112.83(13) . . ?
C12 C13 P1 111.22(15) . . ?
C19 C14 C15 110.1(2) . . ?
C19 C14 P1 110.13(14) . . ?
C15 C14 P1 113.62(15) . . ?
C14 C15 C16 112.1(2) . . ?
C17 C16 C15 112.6(2) . . ?
C18 C17 C16 111.5(2) . . ?
C17 C18 C19 112.3(2) . . ?
C14 C19 C18 112.0(2) . . ?
O2 P1 C6 109.39(8) . . ?
O2 P1 C14 111.38(9) . . ?
C6 P1 C14 106.46(9) . . ?
O2 P1 C13 111.32(9) . . ?
C6 P1 C13 108.68(9) . . ?
C14 P1 C13 109.47(9) . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.042

