# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_No15_1_2
_database_code_depnum_ccdc_archive 'CCDC 2130898'
loop_
_audit_author_name
_audit_author_address
'Makoto Sako'
;Osaka University
Japan
;
_audit_update_record             
;
2021-12-25 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C23 H23 O3 P'
_chemical_formula_moiety         'C23 H23 O3 P'
_chemical_formula_weight         378.41
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.79235(11)
_cell_length_b                   17.5021(3)
_cell_length_c                   19.5063(14)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1977.52(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    28333
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.033
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800.00
_exptl_absorpt_coefficient_mu    1.392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_T_max  0.955

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID 191R'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            39037
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_min         3.393
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3614
_reflns_number_gt                3071
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0873
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3614
_refine_ls_number_parameters     244
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0428P)²+0.4698P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1077 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.548(11)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.2955 0.4335
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.49079(16) 0.11810(5) 0.21617(4) 0.0317(2) Uani 1 1 d . . . . .
O1 O 0.7448(4) 0.11077(14) 0.20745(12) 0.0362(6) Uani 1 1 d . . . . .
O2 O 0.0015(5) -0.03401(13) 0.09132(13) 0.0483(7) Uani 1 1 d . . . . .
O3 O 0.2341(5) -0.13414(14) 0.10849(14) 0.0567(8) Uani 1 1 d . . . . .
C1 C 0.3972(6) 0.07936(19) 0.29710(17) 0.0319(8) Uani 1 1 d . . . . .
C2 C 0.1769(6) 0.04965(19) 0.30967(18) 0.0351(8) Uani 1 1 d . . . . .
H1 H 0.063092 0.050380 0.274618 0.042 Uiso 1 1 calc R U . . .
C3 C 0.1253(7) 0.01912(19) 0.37350(18) 0.0366(8) Uani 1 1 d . . . . .
H2 H -0.023631 -0.001753 0.381566 0.044 Uiso 1 1 calc R U . . .
C4 C 0.2869(7) 0.0186(2) 0.42540(19) 0.0371(9) Uani 1 1 d . . . . .
H3 H 0.249011 -0.002339 0.468886 0.044 Uiso 1 1 calc R U . . .
C5 C 0.5039(7) 0.04865(18) 0.41401(16) 0.0364(8) Uani 1 1 d . . . . .
H4 H 0.615223 0.048956 0.449775 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5588(6) 0.0785(2) 0.34998(18) 0.0357(9) Uani 1 1 d . . . . .
H5 H 0.708960 0.098512 0.342170 0.043 Uiso 1 1 calc R U . . .
C7 C 0.3983(6) 0.2167(2) 0.21546(18) 0.0333(8) Uani 1 1 d . . . . .
C8 C 0.5521(6) 0.2713(2) 0.19053(18) 0.0380(9) Uani 1 1 d . . . . .
H6 H 0.697502 0.255860 0.172780 0.046 Uiso 1 1 calc R U . . .
C9 C 0.4935(7) 0.3485(2) 0.19152(18) 0.0428(9) Uani 1 1 d . . . . .
H7 H 0.598347 0.385448 0.174122 0.051 Uiso 1 1 calc R U . . .
C10 C 0.2827(6) 0.3713(2) 0.21786(19) 0.0400(8) Uani 1 1 d . . . . .
H8 H 0.243577 0.423986 0.219407 0.048 Uiso 1 1 calc R U . . .
C11 C 0.1303(7) 0.3174(2) 0.2418(2) 0.0420(9) Uani 1 1 d . . . . .
H9 H -0.014686 0.333183 0.259600 0.050 Uiso 1 1 calc R U . . .
C12 C 0.1847(7) 0.2405(2) 0.24021(19) 0.0386(9) Uani 1 1 d . . . . .
H10 H 0.076131 0.203832 0.256070 0.046 Uiso 1 1 calc R U . . .
C13 C 0.3719(6) 0.10422(19) 0.08026(17) 0.0313(8) Uani 1 1 d . . . . .
C14 C 0.5827(6) 0.09085(19) 0.04815(18) 0.0321(8) Uani 1 1 d . . . . .
H11 H 0.697251 0.060916 0.070348 0.038 Uiso 1 1 calc R U . . .
C15 C 0.6256(6) 0.1214(2) -0.01657(17) 0.0346(8) Uani 1 1 d . . . . .
H12 H 0.768997 0.112068 -0.038645 0.041 Uiso 1 1 calc R U . . .
C16 C 0.4585(6) 0.16550(19) -0.04875(17) 0.0342(8) Uani 1 1 d . . . . .
H13 H 0.486799 0.185817 -0.093121 0.041 Uiso 1 1 calc R U . . .
C17 C 0.2517(6) 0.1798(2) -0.01637(18) 0.0340(8) Uani 1 1 d . . . . .
H14 H 0.137842 0.210360 -0.038223 0.041 Uiso 1 1 calc R U . . .
C18 C 0.2098(6) 0.14967(19) 0.04791(17) 0.0322(8) Uani 1 1 d . . . . .
H15 H 0.067549 0.160330 0.070212 0.039 Uiso 1 1 calc R U . . .
C19 C 0.3211(6) 0.07015(19) 0.15068(17) 0.0318(8) Uani 1 1 d . . . . .
H16 H 0.154563 0.079770 0.161044 0.038 Uiso 1 1 calc R U . . .
C20 C 0.3602(7) -0.0168(2) 0.15317(19) 0.0384(9) Uani 1 1 d . . . . .
H17A H 0.513525 -0.028771 0.133476 0.046 Uiso 1 1 calc R U . . .
H18B H 0.359816 -0.033925 0.201534 0.046 Uiso 1 1 calc R U . . .
C21 C 0.1763(7) -0.0599(2) 0.11392(19) 0.0388(9) Uani 1 1 d . . . . .
C22 C 0.0629(10) -0.1820(2) 0.0748(2) 0.0730(17) Uani 1 1 d . . . . .
H19B H 0.052036 -0.168721 0.025541 0.088 Uiso 1 1 calc R U . . .
H20A H -0.090674 -0.174474 0.096028 0.088 Uiso 1 1 calc R U . . .
C23 C 0.1393(11) -0.2626(3) 0.0831(3) 0.0885(19) Uani 1 1 d . . . . .
H21B H 0.027784 -0.296738 0.060971 0.106 Uiso 1 1 calc R U . . .
H22A H 0.291294 -0.269274 0.061862 0.106 Uiso 1 1 calc R U . . .
H23C H 0.149217 -0.275001 0.132036 0.106 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.487(2) . ?
P1 C1 1.802(4) . ?
P1 C7 1.807(4) . ?
P1 C19 1.817(4) . ?
O2 C21 1.194(4) . ?
O3 C21 1.347(4) . ?
O3 C22 1.455(5) . ?
C1 C6 1.393(5) . ?
C1 C2 1.400(5) . ?
C2 C3 1.387(5) . ?
C2 H1 0.9500 . ?
C3 C4 1.379(5) . ?
C3 H2 0.9500 . ?
C4 C5 1.380(5) . ?
C4 H3 0.9500 . ?
C5 C6 1.391(5) . ?
C5 H4 0.9500 . ?
C6 H5 0.9500 . ?
C7 C12 1.392(5) . ?
C7 C8 1.394(5) . ?
C8 C9 1.392(5) . ?
C8 H6 0.9500 . ?
C9 C10 1.384(5) . ?
C9 H7 0.9500 . ?
C10 C11 1.374(5) . ?
C10 H8 0.9500 . ?
C11 C12 1.383(5) . ?
C11 H9 0.9500 . ?
C12 H10 0.9500 . ?
C13 C18 1.383(5) . ?
C13 C14 1.392(5) . ?
C13 C19 1.526(4) . ?
C14 C15 1.393(5) . ?
C14 H11 0.9500 . ?
C15 C16 1.388(5) . ?
C15 H12 0.9500 . ?
C16 C17 1.377(5) . ?
C16 H13 0.9500 . ?
C17 C18 1.382(5) . ?
C17 H14 0.9500 . ?
C18 H15 0.9500 . ?
C19 C20 1.539(5) . ?
C19 H16 1.0000 . ?
C20 C21 1.513(5) . ?
C20 H17A 0.9900 . ?
C20 H18B 0.9900 . ?
C22 C23 1.489(6) . ?
C22 H19B 0.9900 . ?
C22 H20A 0.9900 . ?
C23 H21B 0.9800 . ?
C23 H22A 0.9800 . ?
C23 H23C 0.9800 . ?

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 111.44(15) . . ?
O1 P1 C7 112.02(15) . . ?
C1 P1 C7 106.09(16) . . ?
O1 P1 C19 114.52(15) . . ?
C1 P1 C19 106.22(16) . . ?
C7 P1 C19 105.98(15) . . ?
C21 O3 C22 114.9(3) . . ?
C6 C1 C2 118.6(3) . . ?
C6 C1 P1 116.8(3) . . ?
C2 C1 P1 124.6(3) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H1 120.1 . . ?
C1 C2 H1 120.1 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H2 119.5 . . ?
C2 C3 H2 119.5 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H3 120.1 . . ?
C5 C4 H3 120.1 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H4 120.1 . . ?
C6 C5 H4 120.1 . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 H5 119.5 . . ?
C1 C6 H5 119.5 . . ?
C12 C7 C8 119.0(3) . . ?
C12 C7 P1 123.1(3) . . ?
C8 C7 P1 117.9(3) . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H6 119.9 . . ?
C7 C8 H6 119.9 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H7 120.0 . . ?
C8 C9 H7 120.0 . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H8 120.2 . . ?
C9 C10 H8 120.2 . . ?
C10 C11 C12 121.0(4) . . ?
C10 C11 H9 119.5 . . ?
C12 C11 H9 119.5 . . ?
C11 C12 C7 120.1(3) . . ?
C11 C12 H10 120.0 . . ?
C7 C12 H10 120.0 . . ?
C18 C13 C14 119.1(3) . . ?
C18 C13 C19 120.3(3) . . ?
C14 C13 C19 120.6(3) . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H11 120.0 . . ?
C15 C14 H11 120.0 . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H12 120.0 . . ?
C14 C15 H12 120.0 . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 H13 120.0 . . ?
C15 C16 H13 120.0 . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H14 120.0 . . ?
C18 C17 H14 120.0 . . ?
C17 C18 C13 120.9(3) . . ?
C17 C18 H15 119.5 . . ?
C13 C18 H15 119.5 . . ?
C13 C19 C20 112.7(3) . . ?
C13 C19 P1 110.4(2) . . ?
C20 C19 P1 110.8(2) . . ?
C13 C19 H16 107.6 . . ?
C20 C19 H16 107.6 . . ?
P1 C19 H16 107.6 . . ?
C21 C20 C19 111.9(3) . . ?
C21 C20 H17A 109.2 . . ?
C19 C20 H17A 109.2 . . ?
C21 C20 H18B 109.2 . . ?
C19 C20 H18B 109.2 . . ?
H17A C20 H18B 107.9 . . ?
O2 C21 O3 123.2(4) . . ?
O2 C21 C20 126.5(3) . . ?
O3 C21 C20 110.2(3) . . ?
O3 C22 C23 107.1(4) . . ?
O3 C22 H19B 110.3 . . ?
C23 C22 H19B 110.3 . . ?
O3 C22 H20A 110.3 . . ?
C23 C22 H20A 110.3 . . ?
H19B C22 H20A 108.6 . . ?
C22 C23 H21B 109.5 . . ?
C22 C23 H22A 109.5 . . ?
H21B C23 H22A 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H21B C23 H23C 109.5 . . ?
H22A C23 H23C 109.5 . . ?

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 26.1(3) . . . . ?
C7 P1 C1 C6 -96.1(3) . . . . ?
C19 P1 C1 C6 151.4(3) . . . . ?
O1 P1 C1 C2 -153.0(3) . . . . ?
C7 P1 C1 C2 84.8(3) . . . . ?
C19 P1 C1 C2 -27.7(3) . . . . ?
C6 C1 C2 C3 -1.0(5) . . . . ?
P1 C1 C2 C3 178.1(3) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C4 C5 C6 C1 0.8(5) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
P1 C1 C6 C5 -179.1(3) . . . . ?
O1 P1 C7 C12 -162.5(3) . . . . ?
C1 P1 C7 C12 -40.7(3) . . . . ?
C19 P1 C7 C12 72.0(3) . . . . ?
O1 P1 C7 C8 15.7(3) . . . . ?
C1 P1 C7 C8 137.5(3) . . . . ?
C19 P1 C7 C8 -109.8(3) . . . . ?
C12 C7 C8 C9 1.0(5) . . . . ?
P1 C7 C8 C9 -177.3(3) . . . . ?
C7 C8 C9 C10 0.5(5) . . . . ?
C8 C9 C10 C11 -1.2(5) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C11 C12 C7 1.3(6) . . . . ?
C8 C7 C12 C11 -1.9(5) . . . . ?
P1 C7 C12 C11 176.3(3) . . . . ?
C18 C13 C14 C15 -1.8(5) . . . . ?
C19 C13 C14 C15 179.1(3) . . . . ?
C13 C14 C15 C16 0.4(5) . . . . ?
C14 C15 C16 C17 0.8(5) . . . . ?
C15 C16 C17 C18 -0.6(5) . . . . ?
C16 C17 C18 C13 -0.8(5) . . . . ?
C14 C13 C18 C17 2.0(5) . . . . ?
C19 C13 C18 C17 -178.9(3) . . . . ?
C18 C13 C19 C20 127.8(3) . . . . ?
C14 C13 C19 C20 -53.1(4) . . . . ?
C18 C13 C19 P1 -107.7(3) . . . . ?
C14 C13 C19 P1 71.4(3) . . . . ?
O1 P1 C19 C13 -61.7(3) . . . . ?
C1 P1 C19 C13 174.9(2) . . . . ?
C7 P1 C19 C13 62.3(3) . . . . ?
O1 P1 C19 C20 63.9(3) . . . . ?
C1 P1 C19 C20 -59.6(3) . . . . ?
C7 P1 C19 C20 -172.1(3) . . . . ?
C13 C19 C20 C21 -71.7(4) . . . . ?
P1 C19 C20 C21 164.1(2) . . . . ?
C22 O3 C21 O2 -2.0(6) . . . . ?
C22 O3 C21 C20 176.8(4) . . . . ?
C19 C20 C21 O2 -10.3(6) . . . . ?
C19 C20 C21 O3 170.9(3) . . . . ?
C21 O3 C22 C23 -171.5(4) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_No16_11_3_2
_database_code_depnum_ccdc_archive 'CCDC 2130899'
loop_
_audit_author_name
_audit_author_address
'Makoto Sako'
;Osaka University
Japan
;
_audit_update_record             
;
2021-12-25 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H21 O3 P'
_chemical_formula_moiety         'C18 H21 O3 P'
_chemical_formula_weight         316.34
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.4166(6)
_cell_length_b                   20.1330(18)
_cell_length_c                   15.3208(14)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.103(17)
_cell_angle_gamma                90.0000
_cell_volume                     1670.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1776
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      64.72
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.025
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672.00
_exptl_absorpt_coefficient_mu    1.540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_T_max  0.970

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID 191R'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            27195
_diffrn_reflns_av_unetI/netI     0.1429
_diffrn_reflns_av_R_equivalents  0.1664
_diffrn_reflns_theta_max         68.172
_diffrn_reflns_theta_min         3.626
_diffrn_reflns_theta_full        67.687
_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 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3055
_reflns_number_gt                1423
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1888
_refine_ls_R_factor_gt           0.0861
_refine_ls_wR_factor_ref         0.2048
_refine_ls_wR_factor_gt          0.1598
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3055
_refine_ls_number_parameters     199
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0769P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.41
_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 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.2955 0.4335
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.0226(3) 0.10954(7) 0.87514(9) 0.0418(4) Uani 1 1 d . . . . .
O1 O -0.2937(6) 0.10951(17) 0.8571(2) 0.0467(10) Uani 1 1 d . . . . .
O2 O 0.3821(8) 0.30907(19) 0.8408(2) 0.0580(12) Uani 1 1 d . . . . .
O3 O 0.0247(7) 0.3612(2) 0.8689(2) 0.0590(12) Uani 1 1 d . . . . .
C1 C 0.1376(10) 0.0412(3) 0.8311(3) 0.0456(15) Uani 1 1 d . . . . .
H1A H 0.313877 0.045025 0.845860 0.055 Uiso 1 1 calc R U . . .
H2B H 0.072847 -0.000155 0.855497 0.055 Uiso 1 1 calc R U . . .
H3C H 0.114943 0.040756 0.767470 0.055 Uiso 1 1 calc R U . . .
C2 C 0.0461(9) 0.1114(3) 0.9908(3) 0.0410(13) Uani 1 1 d . . . . .
C3 C 0.2634(10) 0.0856(3) 1.0286(4) 0.0446(14) Uani 1 1 d . . . . .
H4 H 0.378205 0.063081 0.992939 0.053 Uiso 1 1 calc R U . . .
C4 C 0.3129(10) 0.0924(3) 1.1172(4) 0.0488(16) Uani 1 1 d . . . . .
H5 H 0.459768 0.074147 1.142113 0.059 Uiso 1 1 calc R U . . .
C5 C 0.1485(11) 0.1258(3) 1.1693(4) 0.0447(15) Uani 1 1 d . . . . .
H6 H 0.182532 0.130828 1.230040 0.054 Uiso 1 1 calc R U . . .
C6 C -0.0651(10) 0.1518(3) 1.1327(4) 0.0456(15) Uani 1 1 d . . . . .
H7 H -0.177344 0.175205 1.168363 0.055 Uiso 1 1 calc R U . . .
C7 C -0.1174(10) 0.1440(3) 1.0447(4) 0.0408(14) Uani 1 1 d . . . . .
H8 H -0.267206 0.161302 1.020729 0.049 Uiso 1 1 calc R U . . .
C8 C 0.1317(10) 0.1835(3) 0.8338(3) 0.0410(14) Uani 1 1 d . . . . .
H9 H 0.308721 0.181136 0.853343 0.049 Uiso 1 1 calc R U . . .
C9 C 0.1264(10) 0.1852(2) 0.7345(4) 0.0401(14) Uani 1 1 d . . . . .
C10 C 0.3208(11) 0.1562(3) 0.6894(4) 0.0453(15) Uani 1 1 d . . . . .
H10 H 0.456746 0.137004 0.720282 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3118(11) 0.1560(3) 0.5986(4) 0.0516(16) Uani 1 1 d . . . . .
H11 H 0.444080 0.136231 0.568151 0.062 Uiso 1 1 calc R U . . .
C12 C 0.1191(12) 0.1833(3) 0.5513(4) 0.0537(16) Uani 1 1 d . . . . .
H12 H 0.116982 0.181877 0.489268 0.064 Uiso 1 1 calc R U . . .
C13 C -0.0709(12) 0.2126(3) 0.5955(4) 0.0531(16) Uani 1 1 d . . . . .
H13 H -0.204885 0.232391 0.564168 0.064 Uiso 1 1 calc R U . . .
C14 C -0.0658(10) 0.2131(3) 0.6866(4) 0.0492(15) Uani 1 1 d . . . . .
H14 H -0.198253 0.233290 0.716489 0.059 Uiso 1 1 calc R U . . .
C15 C 0.0196(10) 0.2458(2) 0.8756(4) 0.0438(15) Uani 1 1 d . . . . .
H15A H -0.151191 0.251869 0.852797 0.053 Uiso 1 1 calc R U . . .
H16B H 0.011497 0.239199 0.939522 0.053 Uiso 1 1 calc R U . . .
C16 C 0.1669(13) 0.3072(3) 0.8573(3) 0.0446(15) Uani 1 1 d . . . . .
C17 C 0.1475(14) 0.4245(3) 0.8600(4) 0.073(2) Uani 1 1 d . . . . .
H17A H 0.224964 0.427832 0.802135 0.088 Uiso 1 1 calc R U . . .
H18B H 0.277516 0.429697 0.905749 0.088 Uiso 1 1 calc R U . . .
C18 C -0.0466(16) 0.4772(3) 0.8693(5) 0.103(3) Uani 1 1 d . . . . .
H19C H 0.029265 0.521104 0.863666 0.124 Uiso 1 1 calc R U . . .
H20B H -0.173970 0.471439 0.823676 0.124 Uiso 1 1 calc R U . . .
H21A H -0.121663 0.473296 0.926809 0.124 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.489(3) . ?
P1 C1 1.768(5) . ?
P1 C2 1.805(5) . ?
P1 C8 1.827(5) . ?
O2 C16 1.198(6) . ?
O3 C16 1.347(6) . ?
O3 C17 1.445(6) . ?
C1 H1A 0.9800 . ?
C1 H2B 0.9800 . ?
C1 H3C 0.9800 . ?
C2 C7 1.388(7) . ?
C2 C3 1.401(7) . ?
C3 C4 1.386(7) . ?
C3 H4 0.9500 . ?
C4 C5 1.382(7) . ?
C4 H5 0.9500 . ?
C5 C6 1.379(7) . ?
C5 H6 0.9500 . ?
C6 C7 1.382(7) . ?
C6 H7 0.9500 . ?
C7 H8 0.9500 . ?
C8 C9 1.522(7) . ?
C8 C15 1.537(7) . ?
C8 H9 1.0000 . ?
C9 C14 1.382(7) . ?
C9 C10 1.398(7) . ?
C10 C11 1.391(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.374(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.376(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(7) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.501(7) . ?
C15 H15A 0.9900 . ?
C15 H16B 0.9900 . ?
C17 C18 1.501(9) . ?
C17 H17A 0.9900 . ?
C17 H18B 0.9900 . ?
C18 H19C 0.9800 . ?
C18 H20B 0.9800 . ?
C18 H21A 0.9800 . ?

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 114.7(2) . . ?
O1 P1 C2 111.5(2) . . ?
C1 P1 C2 107.3(3) . . ?
O1 P1 C8 113.1(2) . . ?
C1 P1 C8 105.7(2) . . ?
C2 P1 C8 103.7(2) . . ?
C16 O3 C17 115.8(5) . . ?
P1 C1 H1A 109.5 . . ?
P1 C1 H2B 109.5 . . ?
H1A C1 H2B 109.5 . . ?
P1 C1 H3C 109.5 . . ?
H1A C1 H3C 109.5 . . ?
H2B C1 H3C 109.5 . . ?
C7 C2 C3 118.1(5) . . ?
C7 C2 P1 118.2(4) . . ?
C3 C2 P1 123.6(4) . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H4 119.6 . . ?
C2 C3 H4 119.6 . . ?
C5 C4 C3 120.0(5) . . ?
C5 C4 H5 120.0 . . ?
C3 C4 H5 120.0 . . ?
C6 C5 C4 119.6(5) . . ?
C6 C5 H6 120.2 . . ?
C4 C5 H6 120.2 . . ?
C5 C6 C7 120.6(6) . . ?
C5 C6 H7 119.7 . . ?
C7 C6 H7 119.7 . . ?
C6 C7 C2 120.8(5) . . ?
C6 C7 H8 119.6 . . ?
C2 C7 H8 119.6 . . ?
C9 C8 C15 113.5(4) . . ?
C9 C8 P1 111.4(4) . . ?
C15 C8 P1 109.5(3) . . ?
C9 C8 H9 107.4 . . ?
C15 C8 H9 107.4 . . ?
P1 C8 H9 107.4 . . ?
C14 C9 C10 118.3(5) . . ?
C14 C9 C8 122.7(5) . . ?
C10 C9 C8 119.0(5) . . ?
C11 C10 C9 118.9(5) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C12 C11 C10 122.6(6) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12 C13 118.6(6) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C12 C13 C14 119.7(6) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C9 C14 C13 121.9(6) . . ?
C9 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C16 C15 C8 112.2(5) . . ?
C16 C15 H15A 109.2 . . ?
C8 C15 H15A 109.2 . . ?
C16 C15 H16B 109.2 . . ?
C8 C15 H16B 109.2 . . ?
H15A C15 H16B 107.9 . . ?
O2 C16 O3 124.3(6) . . ?
O2 C16 C15 126.1(6) . . ?
O3 C16 C15 109.5(5) . . ?
O3 C17 C18 106.8(6) . . ?
O3 C17 H17A 110.4 . . ?
C18 C17 H17A 110.4 . . ?
O3 C17 H18B 110.4 . . ?
C18 C17 H18B 110.4 . . ?
H17A C17 H18B 108.6 . . ?
C17 C18 H19C 109.5 . . ?
C17 C18 H20B 109.5 . . ?
H19C C18 H20B 109.5 . . ?
C17 C18 H21A 109.5 . . ?
H19C C18 H21A 109.5 . . ?
H20B C18 H21A 109.5 . . ?

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 C2 C7 -31.3(5) . . . . ?
C1 P1 C2 C7 -157.7(4) . . . . ?
C8 P1 C2 C7 90.6(4) . . . . ?
O1 P1 C2 C3 153.1(4) . . . . ?
C1 P1 C2 C3 26.7(5) . . . . ?
C8 P1 C2 C3 -84.9(5) . . . . ?
C7 C2 C3 C4 0.1(8) . . . . ?
P1 C2 C3 C4 175.7(4) . . . . ?
C2 C3 C4 C5 -0.9(8) . . . . ?
C3 C4 C5 C6 0.4(8) . . . . ?
C4 C5 C6 C7 0.7(8) . . . . ?
C5 C6 C7 C2 -1.5(8) . . . . ?
C3 C2 C7 C6 1.1(8) . . . . ?
P1 C2 C7 C6 -174.8(4) . . . . ?
O1 P1 C8 C9 -67.5(4) . . . . ?
C1 P1 C8 C9 58.8(4) . . . . ?
C2 P1 C8 C9 171.6(4) . . . . ?
O1 P1 C8 C15 58.8(4) . . . . ?
C1 P1 C8 C15 -174.9(4) . . . . ?
C2 P1 C8 C15 -62.1(4) . . . . ?
C15 C8 C9 C14 -35.9(7) . . . . ?
P1 C8 C9 C14 88.1(5) . . . . ?
C15 C8 C9 C10 145.4(5) . . . . ?
P1 C8 C9 C10 -90.6(5) . . . . ?
C14 C9 C10 C11 -0.7(8) . . . . ?
C8 C9 C10 C11 178.1(5) . . . . ?
C9 C10 C11 C12 0.1(8) . . . . ?
C10 C11 C12 C13 0.8(9) . . . . ?
C11 C12 C13 C14 -1.0(9) . . . . ?
C10 C9 C14 C13 0.5(8) . . . . ?
C8 C9 C14 C13 -178.2(5) . . . . ?
C12 C13 C14 C9 0.4(9) . . . . ?
C9 C8 C15 C16 -65.3(6) . . . . ?
P1 C8 C15 C16 169.7(4) . . . . ?
C17 O3 C16 O2 0.2(8) . . . . ?
C17 O3 C16 C15 175.5(5) . . . . ?
C8 C15 C16 O2 -25.0(8) . . . . ?
C8 C15 C16 O3 159.7(4) . . . . ?
C16 O3 C17 C18 176.3(5) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


