# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_18
_database_code_depnum_ccdc_archive 'CCDC 2395570'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2025-01-14 deposited with the CCDC.	2025-03-06 downloaded from the CCDC.
;
_audit_creation_date             2024-07-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
;
methyl 4-((2R,3R)-2-(dimethoxyphosphoryl)-3-methyl-4-oxooxetan-2-yl)benzoate

;
_chemical_formula_moiety         'C14 H17 O7 P'
_chemical_formula_sum            'C14 H17 O7 P'
_chemical_formula_weight         328.24
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        P1
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.35385(12)
_cell_length_b                   7.76034(15)
_cell_length_c                   16.0686(3)
_cell_angle_alpha                92.9757(16)
_cell_angle_beta                 90.6187(17)
_cell_angle_gamma                101.8462(16)
_cell_volume                     774.21(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    17245
_cell_measurement_temperature    173
_cell_measurement_theta_max      30.4360
_cell_measurement_theta_min      2.5440
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.53a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            43057
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.342
_diffrn_reflns_theta_min         2.539
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P200K'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  89.00   0.50   10.00    --    0.00  -1.00-150.00  356
  2  ω   -108.00 -18.00   0.50   10.00    --  -18.30  -1.00-150.00  180
  3  ω   -108.00  71.00   0.50   10.00    --  -18.30  42.00   0.00  358
  4  ω   -108.00  71.00   0.50   10.00    --  -18.30  42.00-150.00  358
  5  ω   -108.00  71.00   0.50   10.00    --  -18.30  42.00-120.00  358
  6  ω   -108.00  71.00   0.50   10.00    --  -18.30  42.00 150.00  358
  7  ω   -108.00  71.00   0.50   10.00    --  -18.30  42.00  90.00  358
  8  ω   -108.00  71.00   0.50   10.00    --  -18.30  42.00 -90.00  358
  9  ω   -108.00  71.00   0.50   10.00    --  -18.30  42.00 -30.00  358
 10  ω   -108.00  71.00   0.50   10.00    --  -18.30  42.00 -30.00  358
 11  ω   -108.00  71.00   0.50   10.00    --  -18.30  42.00  60.00  358
 12  ω   -108.00  71.00   0.50   10.00    --  -18.30  42.00 -60.00  358
 13  ω   -108.00  71.00   0.50   10.00    --  -18.30  42.00  30.00  358
 14  ω   -108.00  71.00   0.50   10.00    --  -18.30  42.00 120.00  358
;
_diffrn_measurement_device       'AFC11: Quarter χ 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0049953000
_diffrn_orient_matrix_UB_12      -0.0004374000
_diffrn_orient_matrix_UB_13      0.0441056000
_diffrn_orient_matrix_UB_21      0.1001136000
_diffrn_orient_matrix_UB_22      -0.0267796000
_diffrn_orient_matrix_UB_23      -0.0022371000
_diffrn_orient_matrix_UB_31      0.0544867000
_diffrn_orient_matrix_UB_32      0.0896161000
_diffrn_orient_matrix_UB_33      0.0020990000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku FR-X'
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.851
_reflns_number_gt                8109
_reflns_number_total             8979
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 3584 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         8979
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0512P)²+0.0721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0876
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C27(H27)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C29(H29), C30(H30), C32(H32), C33(H33)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C),
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C36(H36A,H36B,H36C), C37(H37A,H37B,
 H37C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.50389(8) 0.21081(7) 0.33824(3) 0.02002(12) Uani 1 1 d . . . . .
P21 P 0.53533(8) 0.48495(7) 0.65982(3) 0.02030(12) Uani 1 1 d . . . . .
O1 O 0.6531(3) 0.2237(3) 0.40956(11) 0.0296(4) Uani 1 1 d . . . . .
O2 O 0.5783(3) 0.1374(2) 0.25292(10) 0.0262(4) Uani 1 1 d . . . . .
O3 O 0.2738(3) 0.0945(2) 0.34876(10) 0.0273(4) Uani 1 1 d . . . . .
O5 O 0.6691(2) 0.5502(2) 0.31449(10) 0.0236(3) Uani 1 1 d . . . . .
O6 O 0.7312(3) 0.7560(3) 0.42379(12) 0.0339(4) Uani 1 1 d . . . . .
O14 O 0.1035(4) 0.4721(4) -0.06584(13) 0.0625(7) Uani 1 1 d . . . . .
O15 O -0.1907(3) 0.3259(3) -0.00681(12) 0.0442(5) Uani 1 1 d . . . . .
O21 O 0.4023(3) 0.4337(2) 0.58381(10) 0.0261(4) Uani 1 1 d . . . . .
O22 O 0.4652(3) 0.3754(2) 0.73807(11) 0.0311(4) Uani 1 1 d . . . . .
O23 O 0.7773(3) 0.4730(2) 0.65504(11) 0.0281(4) Uani 1 1 d . . . . .
O25 O 0.3064(3) 0.7277(2) 0.69768(10) 0.0253(3) Uani 1 1 d . . . . .
O26 O 0.1909(3) 0.8967(3) 0.60175(13) 0.0386(5) Uani 1 1 d . . . . .
O34 O 0.8855(4) 0.8603(4) 1.07713(13) 0.0595(7) Uani 1 1 d . . . . .
O35 O 1.1845(3) 0.9674(3) 1.00829(12) 0.0428(5) Uani 1 1 d . . . . .
C2 C 0.6639(5) -0.0225(4) 0.25079(16) 0.0342(6) Uani 1 1 d . . . . .
H2A H 0.749301 -0.028242 0.200682 0.051 Uiso 1 1 calc R U . . .
H2B H 0.544911 -0.125413 0.249842 0.051 Uiso 1 1 calc R U . . .
H2C H 0.755232 -0.021660 0.300403 0.051 Uiso 1 1 calc R U . . .
C3 C 0.1621(5) 0.0961(4) 0.42787(17) 0.0346(6) Uani 1 1 d . . . . .
H3A H 0.068368 0.181837 0.427088 0.052 Uiso 1 1 calc R U . . .
H3B H 0.267922 0.129173 0.473756 0.052 Uiso 1 1 calc R U . . .
H3C H 0.075200 -0.021463 0.435744 0.052 Uiso 1 1 calc R U . . .
C4 C 0.4569(3) 0.4263(3) 0.31228(13) 0.0192(4) Uani 1 1 d . . . . .
C6 C 0.6175(4) 0.6364(3) 0.38590(14) 0.0226(4) Uani 1 1 d . . . . .
C7 C 0.3926(4) 0.5268(3) 0.39232(13) 0.0210(4) Uani 1 1 d . . . . .
H7 H 0.380910 0.451995 0.441566 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3372(3) 0.4286(3) 0.23081(13) 0.0195(4) Uani 1 1 d . . . . .
C9 C 0.4483(4) 0.4930(3) 0.16133(14) 0.0250(5) Uani 1 1 d . . . . .
H9 H 0.598198 0.541663 0.165752 0.030 Uiso 1 1 calc R U . . .
C10 C 0.3396(4) 0.4862(4) 0.08495(15) 0.0286(5) Uani 1 1 d . . . . .
H10 H 0.416170 0.529478 0.037337 0.034 Uiso 1 1 calc R U . . .
C11 C 0.1200(4) 0.4164(3) 0.07807(14) 0.0272(5) Uani 1 1 d . . . . .
C12 C 0.0076(4) 0.3537(3) 0.14814(14) 0.0261(5) Uani 1 1 d . . . . .
H12 H -0.142722 0.306945 0.143895 0.031 Uiso 1 1 calc R U . . .
C13 C 0.1159(4) 0.3598(3) 0.22415(13) 0.0240(5) Uani 1 1 d . . . . .
H13 H 0.039302 0.316983 0.271829 0.029 Uiso 1 1 calc R U . . .
C14 C 0.0129(5) 0.4097(4) -0.00561(15) 0.0345(6) Uani 1 1 d . . . . .
C16 C -0.3049(6) 0.3120(5) -0.08653(19) 0.0536(9) Uani 1 1 d . . . . .
H16A H -0.240889 0.239350 -0.126610 0.080 Uiso 1 1 calc R U . . .
H16B H -0.294369 0.429961 -0.107267 0.080 Uiso 1 1 calc R U . . .
H16C H -0.456531 0.257354 -0.079453 0.080 Uiso 1 1 calc R U . . .
C17 C 0.2096(4) 0.6244(4) 0.38871(17) 0.0328(6) Uani 1 1 d . . . . .
H17A H 0.215276 0.703094 0.438762 0.049 Uiso 1 1 calc R U . . .
H17B H 0.072177 0.539296 0.385885 0.049 Uiso 1 1 calc R U . . .
H17C H 0.223067 0.693995 0.339146 0.049 Uiso 1 1 calc R U . . .
C22 C 0.2407(5) 0.3015(5) 0.7504(2) 0.0485(8) Uani 1 1 d . . . . .
H22A H 0.185310 0.216583 0.704097 0.073 Uiso 1 1 calc R U . . .
H22B H 0.159492 0.396153 0.752642 0.073 Uiso 1 1 calc R U . . .
H22C H 0.224945 0.241636 0.802902 0.073 Uiso 1 1 calc R U . . .
C23 C 0.8829(4) 0.4823(4) 0.57479(16) 0.0314(5) Uani 1 1 d . . . . .
H23A H 0.793646 0.400295 0.533778 0.047 Uiso 1 1 calc R U . . .
H23B H 1.023401 0.450130 0.580604 0.047 Uiso 1 1 calc R U . . .
H23C H 0.902459 0.602581 0.556046 0.047 Uiso 1 1 calc R U . . .
C24 C 0.5372(3) 0.7147(3) 0.69368(13) 0.0207(4) Uani 1 1 d . . . . .
C26 C 0.3280(4) 0.8347(3) 0.63149(15) 0.0260(5) Uani 1 1 d . . . . .
C27 C 0.5654(4) 0.8404(3) 0.61954(14) 0.0230(4) Uani 1 1 d . . . . .
H27 H 0.590579 0.776198 0.566181 0.028 Uiso 1 1 calc R U . . .
C28 C 0.6518(4) 0.7739(3) 0.77584(13) 0.0217(4) Uani 1 1 d . . . . .
C29 C 0.5361(4) 0.7612(3) 0.84943(14) 0.0256(5) Uani 1 1 d . . . . .
H29 H 0.384204 0.722520 0.847379 0.031 Uiso 1 1 calc R U . . .
C30 C 0.6435(4) 0.8053(3) 0.92531(14) 0.0291(5) Uani 1 1 d . . . . .
H30 H 0.564422 0.797376 0.975289 0.035 Uiso 1 1 calc R U . . .
C31 C 0.8664(4) 0.8612(3) 0.92925(14) 0.0271(5) Uani 1 1 d . . . . .
C32 C 0.9816(4) 0.8755(4) 0.85564(15) 0.0289(5) Uani 1 1 d . . . . .
H32 H 1.133339 0.915773 0.857651 0.035 Uiso 1 1 calc R U . . .
C33 C 0.8737(4) 0.8305(3) 0.77919(14) 0.0269(5) Uani 1 1 d . . . . .
H33 H 0.952328 0.838690 0.729107 0.032 Uiso 1 1 calc R U . . .
C34 C 0.9750(5) 0.8956(4) 1.01289(16) 0.0351(6) Uani 1 1 d . . . . .
C36 C 1.3036(6) 0.9963(5) 1.08699(19) 0.0490(8) Uani 1 1 d . . . . .
H36A H 1.452945 1.054121 1.077527 0.073 Uiso 1 1 calc R U . . .
H36B H 1.300505 0.882865 1.111521 0.073 Uiso 1 1 calc R U . . .
H36C H 1.237756 1.071630 1.125130 0.073 Uiso 1 1 calc R U . . .
C37 C 0.7063(4) 1.0240(4) 0.62693(19) 0.0358(6) Uani 1 1 d . . . . .
H37A H 0.662432 1.095676 0.584098 0.054 Uiso 1 1 calc R U . . .
H37B H 0.856877 1.016080 0.619228 0.054 Uiso 1 1 calc R U . . .
H37C H 0.690532 1.078692 0.682234 0.054 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 1.4657(18) . ?
P1 O2 1.5721(17) . ?
P1 O3 1.5687(18) . ?
P1 C4 1.826(2) . ?
P21 O21 1.4676(17) . ?
P21 O22 1.5717(18) . ?
P21 O23 1.5615(18) . ?
P21 C24 1.835(2) . ?
O2 C2 1.452(3) . ?
O3 C3 1.463(3) . ?
O5 C4 1.486(3) . ?
O5 C6 1.375(3) . ?
O6 C6 1.188(3) . ?
O14 C14 1.204(4) . ?
O15 C14 1.322(4) . ?
O15 C16 1.454(3) . ?
O22 C22 1.444(4) . ?
O23 C23 1.458(3) . ?
O25 C24 1.492(3) . ?
O25 C26 1.374(3) . ?
O26 C26 1.186(3) . ?
O34 C34 1.201(4) . ?
O35 C34 1.338(4) . ?
O35 C36 1.450(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C7 1.571(3) . ?
C4 C8 1.509(3) . ?
C6 C7 1.513(3) . ?
C7 H7 1.0000 . ?
C7 C17 1.514(3) . ?
C8 C9 1.387(3) . ?
C8 C13 1.399(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.395(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(4) . ?
C11 C12 1.395(3) . ?
C11 C14 1.494(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(3) . ?
C13 H13 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C27 1.567(3) . ?
C24 C28 1.505(3) . ?
C26 C27 1.514(3) . ?
C27 H27 1.0000 . ?
C27 C37 1.517(4) . ?
C28 C29 1.396(3) . ?
C28 C33 1.387(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.383(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.393(4) . ?
C31 C32 1.395(3) . ?
C31 C34 1.490(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.393(3) . ?
C33 H33 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 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 O2 116.53(10) . . ?
O1 P1 O3 116.00(10) . . ?
O1 P1 C4 112.01(11) . . ?
O2 P1 C4 102.38(9) . . ?
O3 P1 O2 103.45(10) . . ?
O3 P1 C4 104.91(10) . . ?
O21 P21 O22 116.45(10) . . ?
O21 P21 O23 117.20(9) . . ?
O21 P21 C24 110.52(10) . . ?
O22 P21 C24 105.33(10) . . ?
O23 P21 O22 100.82(10) . . ?
O23 P21 C24 105.21(10) . . ?
C2 O2 P1 119.21(15) . . ?
C3 O3 P1 121.34(16) . . ?
C6 O5 C4 91.27(16) . . ?
C14 O15 C16 116.1(2) . . ?
C22 O22 P21 120.07(18) . . ?
C23 O23 P21 119.74(15) . . ?
C26 O25 C24 91.30(16) . . ?
C34 O35 C36 115.6(2) . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O3 C3 H3A 109.5 . . ?
O3 C3 H3B 109.5 . . ?
O3 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O5 C4 P1 107.37(13) . . ?
O5 C4 C7 89.38(15) . . ?
O5 C4 C8 111.57(17) . . ?
C7 C4 P1 110.09(14) . . ?
C8 C4 P1 115.16(15) . . ?
C8 C4 C7 119.84(17) . . ?
O5 C6 C7 96.15(17) . . ?
O6 C6 O5 126.1(2) . . ?
O6 C6 C7 137.7(2) . . ?
C4 C7 H7 111.3 . . ?
C6 C7 C4 83.15(16) . . ?
C6 C7 H7 111.3 . . ?
C6 C7 C17 116.6(2) . . ?
C17 C7 C4 120.52(19) . . ?
C17 C7 H7 111.3 . . ?
C9 C8 C4 119.95(19) . . ?
C9 C8 C13 119.7(2) . . ?
C13 C8 C4 120.27(18) . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.9(2) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 C14 118.1(2) . . ?
C12 C11 C14 122.2(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.3(2) . . ?
C12 C13 H13 119.8 . . ?
O14 C14 O15 123.6(2) . . ?
O14 C14 C11 123.4(3) . . ?
O15 C14 C11 113.0(2) . . ?
O15 C16 H16A 109.5 . . ?
O15 C16 H16B 109.5 . . ?
O15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O22 C22 H22A 109.5 . . ?
O22 C22 H22B 109.5 . . ?
O22 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O23 C23 H23A 109.5 . . ?
O23 C23 H23B 109.5 . . ?
O23 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O25 C24 P21 105.54(15) . . ?
O25 C24 C27 89.21(15) . . ?
O25 C24 C28 110.93(17) . . ?
C27 C24 P21 112.64(15) . . ?
C28 C24 P21 114.35(15) . . ?
C28 C24 C27 120.27(19) . . ?
O25 C26 C27 96.02(17) . . ?
O26 C26 O25 126.1(2) . . ?
O26 C26 C27 137.8(2) . . ?
C24 C27 H27 111.2 . . ?
C26 C27 C24 83.44(16) . . ?
C26 C27 H27 111.2 . . ?
C26 C27 C37 114.5(2) . . ?
C37 C27 C24 122.3(2) . . ?
C37 C27 H27 111.2 . . ?
C29 C28 C24 119.8(2) . . ?
C33 C28 C24 120.18(19) . . ?
C33 C28 C29 119.9(2) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.8(2) . . ?
C30 C29 H29 120.1 . . ?
C29 C30 H30 119.6 . . ?
C29 C30 C31 120.7(2) . . ?
C31 C30 H30 119.6 . . ?
C30 C31 C32 119.5(2) . . ?
C30 C31 C34 118.4(2) . . ?
C32 C31 C34 122.1(2) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 C31 119.8(2) . . ?
C33 C32 H32 120.1 . . ?
C28 C33 C32 120.3(2) . . ?
C28 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
O34 C34 O35 123.7(3) . . ?
O34 C34 C31 123.9(3) . . ?
O35 C34 C31 112.4(2) . . ?
O35 C36 H36A 109.5 . . ?
O35 C36 H36B 109.5 . . ?
O35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C27 C37 H37A 109.5 . . ?
C27 C37 H37B 109.5 . . ?
C27 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 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
P1 C4 C7 C6 106.84(15) . . . . ?
P1 C4 C7 C17 -136.3(2) . . . . ?
P1 C4 C8 C9 -103.0(2) . . . . ?
P1 C4 C8 C13 74.5(2) . . . . ?
P21 C24 C27 C26 105.37(16) . . . . ?
P21 C24 C27 C37 -139.67(19) . . . . ?
P21 C24 C28 C29 -92.9(2) . . . . ?
P21 C24 C28 C33 83.1(2) . . . . ?
O1 P1 O2 C2 47.9(2) . . . . ?
O1 P1 O3 C3 39.3(2) . . . . ?
O1 P1 C4 O5 44.69(16) . . . . ?
O1 P1 C4 C7 -51.18(17) . . . . ?
O1 P1 C4 C8 169.61(15) . . . . ?
O2 P1 O3 C3 168.15(18) . . . . ?
O2 P1 C4 O5 -80.90(14) . . . . ?
O2 P1 C4 C7 -176.77(15) . . . . ?
O2 P1 C4 C8 44.02(17) . . . . ?
O3 P1 O2 C2 -80.7(2) . . . . ?
O3 P1 C4 O5 171.34(12) . . . . ?
O3 P1 C4 C7 75.47(16) . . . . ?
O3 P1 C4 C8 -63.74(17) . . . . ?
O5 C4 C7 C6 -1.45(14) . . . . ?
O5 C4 C7 C17 115.4(2) . . . . ?
O5 C4 C8 C9 19.7(3) . . . . ?
O5 C4 C8 C13 -162.84(19) . . . . ?
O5 C6 C7 C4 1.58(16) . . . . ?
O5 C6 C7 C17 -119.2(2) . . . . ?
O6 C6 C7 C4 -177.9(3) . . . . ?
O6 C6 C7 C17 61.3(4) . . . . ?
O21 P21 O22 C22 -31.5(3) . . . . ?
O21 P21 O23 C23 24.3(2) . . . . ?
O21 P21 C24 O25 52.11(16) . . . . ?
O21 P21 C24 C27 -43.66(17) . . . . ?
O21 P21 C24 C28 174.31(16) . . . . ?
O22 P21 O23 C23 151.72(19) . . . . ?
O22 P21 C24 O25 -74.45(15) . . . . ?
O22 P21 C24 C27 -170.22(15) . . . . ?
O22 P21 C24 C28 47.75(18) . . . . ?
O23 P21 O22 C22 -159.5(2) . . . . ?
O23 P21 C24 O25 179.52(13) . . . . ?
O23 P21 C24 C27 83.75(16) . . . . ?
O23 P21 C24 C28 -58.28(18) . . . . ?
O25 C24 C27 C26 -1.17(16) . . . . ?
O25 C24 C27 C37 113.8(2) . . . . ?
O25 C24 C28 C29 26.3(3) . . . . ?
O25 C24 C28 C33 -157.7(2) . . . . ?
O25 C26 C27 C24 1.28(17) . . . . ?
O25 C26 C27 C37 -121.3(2) . . . . ?
O26 C26 C27 C24 179.1(3) . . . . ?
O26 C26 C27 C37 56.5(4) . . . . ?
C4 P1 O2 C2 170.47(19) . . . . ?
C4 P1 O3 C3 -84.9(2) . . . . ?
C4 O5 C6 O6 177.9(2) . . . . ?
C4 O5 C6 C7 -1.66(16) . . . . ?
C4 C8 C9 C10 176.5(2) . . . . ?
C4 C8 C13 C12 -176.7(2) . . . . ?
C6 O5 C4 P1 -109.30(14) . . . . ?
C6 O5 C4 C7 1.59(16) . . . . ?
C6 O5 C4 C8 123.64(18) . . . . ?
C7 C4 C8 C9 122.0(2) . . . . ?
C7 C4 C8 C13 -60.5(3) . . . . ?
C8 C4 C7 C6 -116.1(2) . . . . ?
C8 C4 C7 C17 0.7(3) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C9 C8 C13 C12 0.8(3) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C9 C10 C11 C14 -179.0(2) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C10 C11 C14 O14 -5.1(4) . . . . ?
C10 C11 C14 O15 173.9(2) . . . . ?
C11 C12 C13 C8 0.1(4) . . . . ?
C12 C11 C14 O14 175.6(3) . . . . ?
C12 C11 C14 O15 -5.4(4) . . . . ?
C13 C8 C9 C10 -1.0(3) . . . . ?
C14 C11 C12 C13 178.7(2) . . . . ?
C16 O15 C14 O14 -0.2(5) . . . . ?
C16 O15 C14 C11 -179.2(2) . . . . ?
C24 P21 O22 C22 91.3(2) . . . . ?
C24 P21 O23 C23 -98.96(19) . . . . ?
C24 O25 C26 O26 -179.5(3) . . . . ?
C24 O25 C26 C27 -1.33(18) . . . . ?
C24 C28 C29 C30 176.0(2) . . . . ?
C24 C28 C33 C32 -176.2(2) . . . . ?
C26 O25 C24 P21 -112.03(16) . . . . ?
C26 O25 C24 C27 1.28(17) . . . . ?
C26 O25 C24 C28 123.6(2) . . . . ?
C27 C24 C28 C29 128.2(2) . . . . ?
C27 C24 C28 C33 -55.8(3) . . . . ?
C28 C24 C27 C26 -115.1(2) . . . . ?
C28 C24 C27 C37 -0.1(3) . . . . ?
C28 C29 C30 C31 -0.4(4) . . . . ?
C29 C28 C33 C32 -0.2(4) . . . . ?
C29 C30 C31 C32 1.1(4) . . . . ?
C29 C30 C31 C34 -176.0(2) . . . . ?
C30 C31 C32 C33 -1.3(4) . . . . ?
C30 C31 C34 O34 8.3(4) . . . . ?
C30 C31 C34 O35 -172.8(2) . . . . ?
C31 C32 C33 C28 0.9(4) . . . . ?
C32 C31 C34 O34 -168.7(3) . . . . ?
C32 C31 C34 O35 10.1(4) . . . . ?
C33 C28 C29 C30 0.0(4) . . . . ?
C34 C31 C32 C33 175.7(2) . . . . ?
C36 O35 C34 O34 1.9(4) . . . . ?
C36 O35 C34 C31 -177.0(2) . . . . ?


#==END

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/hexane'
####################################################################### 
# 
# 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_26
_database_code_depnum_ccdc_archive 'CCDC 2395571'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2025-01-14 deposited with the CCDC.	2025-03-06 downloaded from the CCDC.
;
_audit_creation_date             2024-07-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
;
dimethyl ((2R,3R)-3-methyl-2-naphthalen-2-yl-4-oxooxetan-2-yl)phosphonate
;
_chemical_formula_moiety         'C16 H17 O5 P'
_chemical_formula_sum            'C16 H17 O5 P'
_chemical_formula_weight         320.26
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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 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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        P212121
_space_group_name_Hall           'P 2ac 2ab'
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                   6.2790(2)
_cell_length_b                   8.1645(3)
_cell_length_c                   30.2310(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1549.79(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11547
_cell_measurement_temperature    173
_cell_measurement_theta_max      67.8940
_cell_measurement_theta_min      5.7940
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.569
_exptl_absorpt_coefficient_mu    1.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0915
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16081
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.319
_diffrn_reflns_theta_min         2.923
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Dectris PILATUS P100K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ      0.00 200.00   0.50    1.00   0.00 -30.00   0.00    --   400
  2  ω    -72.00   1.00   0.50    1.00    --  -30.00 -72.00 -90.00  146
  3  ω   -111.00 -69.00   0.50    1.00    --  -30.00 180.00 -45.00   84
  4  φ      0.00 200.00   0.50    1.00   0.00 -67.00   0.00    --   400
  5  ω    -83.00 -11.00   0.50    1.00    --  -67.00  72.00  90.00  144
  6  ω   -133.00 -93.00   0.50    1.00    --  -67.00 180.00   0.00   80
  7  ω    -83.00 -10.00   0.50    1.00    --  -67.00  72.00 -90.00  146
  8  ω   -126.00 -86.00   0.50    1.00    --  -67.00 180.00-180.00   80
  9  φ      0.00 200.00   0.50    1.00 -25.00-110.00   0.00    --   400
 10  ω   -126.00 -20.00   0.50    1.00    -- -110.00  72.00-135.00  212
 11  ω   -126.00 -20.00   0.50    1.00    -- -110.00  72.00  45.00  212
 12  ω   -115.00 -20.00   0.50    1.00    -- -110.00  72.00 -45.00  190
 13  ω   -113.00 -23.00   0.50    1.00    -- -110.00  72.00 135.00  180
 14  ω   -141.00 -46.00   0.50    1.00    -- -110.00 180.00 -90.00  190
 15  ω   -141.00 -46.00   0.50    1.00    -- -110.00 180.00-180.00  190
 16  ω   -141.00 -59.00   0.50    1.00    -- -110.00 180.00  90.00  164
 17  ω   -141.00 -55.00   0.50    1.00    -- -110.00 180.00   0.00  172
 18  ω   -141.00 -59.00   0.50    1.00    -- -110.00 180.00  45.00  164
 19  ω   -141.00 -78.00   0.50    1.00    -- -110.00 180.00 -45.00  126
 20  ω   -140.00 -77.00   0.50    1.00    -- -110.00 180.00-135.00  126
 21  ω   -140.00 -56.00   0.50    1.00    -- -110.00 180.00 135.00  168
;
_diffrn_measurement_device       'AFC12: Kappa 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P100K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2352868000
_diffrn_orient_matrix_UB_12      -0.0399899000
_diffrn_orient_matrix_UB_13      -0.0096502000
_diffrn_orient_matrix_UB_21      0.0394612000
_diffrn_orient_matrix_UB_22      0.1800077000
_diffrn_orient_matrix_UB_23      -0.0128342000
_diffrn_orient_matrix_UB_31      0.0575195000
_diffrn_orient_matrix_UB_32      0.0399688000
_diffrn_orient_matrix_UB_33      0.0483540000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2601
_reflns_number_total             2816
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 
;
 Flack x determined using 997 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2816
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0895P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1135
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.60654(15) 0.35676(11) 0.69715(3) 0.0324(3) Uani 1 1 d . . . . .
O1 O 0.4246(5) 0.3236(4) 0.72575(8) 0.0452(7) Uani 1 1 d . . . . .
O2 O 0.7734(5) 0.4864(4) 0.71301(9) 0.0473(7) Uani 1 1 d . . . . .
O3 O 0.7497(4) 0.2034(3) 0.68676(8) 0.0364(6) Uani 1 1 d . . . . .
O5 O 0.7218(4) 0.5092(3) 0.62123(8) 0.0349(6) Uani 1 1 d . . . . .
O6 O 0.7248(6) 0.7816(4) 0.60541(10) 0.0552(9) Uani 1 1 d . . . . .
C2 C 0.8895(8) 0.4675(7) 0.75358(13) 0.0536(11) Uani 1 1 d . . . . .
H2A H 1.032358 0.425373 0.747143 0.080 Uiso 1 1 calc R U . . .
H2B H 0.814351 0.390244 0.772872 0.080 Uiso 1 1 calc R U . . .
H2C H 0.901128 0.573803 0.768413 0.080 Uiso 1 1 calc R U . . .
C3 C 0.6548(8) 0.0431(5) 0.68278(13) 0.0459(10) Uani 1 1 d . . . . .
H3A H 0.544457 0.045398 0.659854 0.069 Uiso 1 1 calc R U . . .
H3B H 0.590777 0.011745 0.711109 0.069 Uiso 1 1 calc R U . . .
H3C H 0.764605 -0.036722 0.674675 0.069 Uiso 1 1 calc R U . . .
C4 C 0.5300(6) 0.4463(5) 0.64433(11) 0.0318(8) Uani 1 1 d . . . . .
C6 C 0.6434(6) 0.6657(5) 0.62224(12) 0.0395(9) Uani 1 1 d . . . . .
C7 C 0.4447(6) 0.6263(5) 0.64795(12) 0.0370(8) Uani 1 1 d . . . . .
H7 H 0.455870 0.667286 0.679027 0.044 Uiso 1 1 calc R U . . .
C8 C 0.4126(6) 0.3254(4) 0.61540(10) 0.0298(7) Uani 1 1 d . . . . .
C9 C 0.5049(5) 0.2665(4) 0.57783(11) 0.0291(7) Uani 1 1 d . . . . .
H9 H 0.641251 0.305795 0.569295 0.035 Uiso 1 1 calc R U . . .
C10 C 0.4012(5) 0.1475(4) 0.55119(10) 0.0278(7) Uani 1 1 d . . . . .
C11 C 0.4950(6) 0.0856(5) 0.51205(11) 0.0343(8) Uani 1 1 d . . . . .
H11 H 0.631739 0.123025 0.503142 0.041 Uiso 1 1 calc R U . . .
C12 C 0.3894(7) -0.0280(5) 0.48699(11) 0.0390(8) Uani 1 1 d . . . . .
H12 H 0.453164 -0.068585 0.460692 0.047 Uiso 1 1 calc R U . . .
C13 C 0.1862(7) -0.0855(5) 0.49988(12) 0.0404(9) Uani 1 1 d . . . . .
H13 H 0.114955 -0.164953 0.482324 0.049 Uiso 1 1 calc R U . . .
C14 C 0.0923(7) -0.0277(5) 0.53728(11) 0.0372(8) Uani 1 1 d . . . . .
H14 H -0.044001 -0.067419 0.545696 0.045 Uiso 1 1 calc R U . . .
C15 C 0.1958(6) 0.0915(5) 0.56388(10) 0.0305(7) Uani 1 1 d . . . . .
C16 C 0.1029(6) 0.1556(5) 0.60277(11) 0.0343(7) Uani 1 1 d . . . . .
H16 H -0.034364 0.119011 0.611538 0.041 Uiso 1 1 calc R U . . .
C17 C 0.2073(6) 0.2695(5) 0.62813(11) 0.0333(8) Uani 1 1 d . . . . .
H17 H 0.142188 0.311095 0.654183 0.040 Uiso 1 1 calc R U . . .
C18 C 0.2337(8) 0.6736(6) 0.62777(18) 0.0579(12) Uani 1 1 d . . . . .
H18A H 0.224485 0.629672 0.597664 0.087 Uiso 1 1 calc R U . . .
H18B H 0.221844 0.793215 0.626839 0.087 Uiso 1 1 calc R U . . .
H18C H 0.117600 0.628578 0.645720 0.087 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 1.458(3) . ?
P1 O2 1.564(3) . ?
P1 O3 1.573(3) . ?
P1 C4 1.821(4) . ?
O2 C2 1.435(5) . ?
O3 C3 1.444(5) . ?
O5 C4 1.484(4) . ?
O5 C6 1.370(5) . ?
O6 C6 1.190(5) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C7 1.567(5) . ?
C4 C8 1.511(5) . ?
C6 C7 1.505(5) . ?
C7 H7 1.0000 . ?
C7 C18 1.509(6) . ?
C8 C9 1.363(5) . ?
C8 C17 1.421(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.420(5) . ?
C10 C11 1.415(5) . ?
C10 C15 1.421(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.369(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.414(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.360(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.420(5) . ?
C15 C16 1.413(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.372(5) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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 O2 117.96(16) . . ?
O1 P1 O3 114.73(17) . . ?
O1 P1 C4 112.80(17) . . ?
O2 P1 O3 102.54(17) . . ?
O2 P1 C4 100.00(16) . . ?
O3 P1 C4 107.17(15) . . ?
C2 O2 P1 121.9(3) . . ?
C3 O3 P1 120.2(3) . . ?
C6 O5 C4 91.2(3) . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O3 C3 H3A 109.5 . . ?
O3 C3 H3B 109.5 . . ?
O3 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O5 C4 P1 109.7(2) . . ?
O5 C4 C7 89.2(3) . . ?
O5 C4 C8 110.5(3) . . ?
C7 C4 P1 113.9(2) . . ?
C8 C4 P1 112.0(2) . . ?
C8 C4 C7 119.1(3) . . ?
O5 C6 C7 96.3(3) . . ?
O6 C6 O5 125.3(4) . . ?
O6 C6 C7 138.4(4) . . ?
C4 C7 H7 110.8 . . ?
C6 C7 C4 83.2(3) . . ?
C6 C7 H7 110.8 . . ?
C6 C7 C18 117.7(3) . . ?
C18 C7 C4 120.8(3) . . ?
C18 C7 H7 110.8 . . ?
C9 C8 C4 120.4(3) . . ?
C9 C8 C17 119.9(3) . . ?
C17 C8 C4 119.7(3) . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.3(3) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C15 118.9(3) . . ?
C11 C10 C9 121.8(3) . . ?
C11 C10 C15 119.3(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(4) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.3(4) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.7(4) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C10 118.9(3) . . ?
C16 C15 C10 118.7(3) . . ?
C16 C15 C14 122.4(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.3(3) . . ?
C17 C16 H16 119.4 . . ?
C8 C17 H17 120.0 . . ?
C16 C17 C8 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C7 C18 H18A 109.5 . . ?
C7 C18 H18B 109.5 . . ?
C7 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
P1 C4 C7 C6 113.9(3) . . . . ?
P1 C4 C7 C18 -127.8(4) . . . . ?
P1 C4 C8 C9 -111.1(3) . . . . ?
P1 C4 C8 C17 67.2(4) . . . . ?
O1 P1 O2 C2 59.9(4) . . . . ?
O1 P1 O3 C3 33.7(3) . . . . ?
O1 P1 C4 O5 167.9(2) . . . . ?
O1 P1 C4 C7 69.7(3) . . . . ?
O1 P1 C4 C8 -69.1(3) . . . . ?
O2 P1 O3 C3 162.9(3) . . . . ?
O2 P1 C4 O5 41.7(3) . . . . ?
O2 P1 C4 C7 -56.5(3) . . . . ?
O2 P1 C4 C8 164.7(3) . . . . ?
O3 P1 O2 C2 -67.2(3) . . . . ?
O3 P1 C4 O5 -64.9(3) . . . . ?
O3 P1 C4 C7 -163.0(2) . . . . ?
O3 P1 C4 C8 58.2(3) . . . . ?
O5 C4 C7 C6 2.7(2) . . . . ?
O5 C4 C7 C18 120.9(4) . . . . ?
O5 C4 C8 C9 11.5(5) . . . . ?
O5 C4 C8 C17 -170.2(3) . . . . ?
O5 C6 C7 C4 -2.9(3) . . . . ?
O5 C6 C7 C18 -124.2(4) . . . . ?
O6 C6 C7 C4 175.2(5) . . . . ?
O6 C6 C7 C18 53.9(7) . . . . ?
C4 P1 O2 C2 -177.5(3) . . . . ?
C4 P1 O3 C3 -92.3(3) . . . . ?
C4 O5 C6 O6 -175.4(4) . . . . ?
C4 O5 C6 C7 3.0(3) . . . . ?
C4 C8 C9 C10 177.3(3) . . . . ?
C4 C8 C17 C16 -177.8(3) . . . . ?
C6 O5 C4 P1 -118.1(3) . . . . ?
C6 O5 C4 C7 -2.9(3) . . . . ?
C6 O5 C4 C8 118.0(3) . . . . ?
C7 C4 C8 C9 112.5(4) . . . . ?
C7 C4 C8 C17 -69.2(4) . . . . ?
C8 C4 C7 C6 -110.4(3) . . . . ?
C8 C4 C7 C18 7.8(5) . . . . ?
C8 C9 C10 C11 179.8(3) . . . . ?
C8 C9 C10 C15 1.0(5) . . . . ?
C9 C8 C17 C16 0.5(5) . . . . ?
C9 C10 C11 C12 -179.4(3) . . . . ?
C9 C10 C15 C14 -179.9(3) . . . . ?
C9 C10 C15 C16 -0.5(5) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C10 C15 C16 C17 0.0(5) . . . . ?
C11 C10 C15 C14 1.2(5) . . . . ?
C11 C10 C15 C16 -179.3(3) . . . . ?
C11 C12 C13 C14 0.5(6) . . . . ?
C12 C13 C14 C15 0.2(6) . . . . ?
C13 C14 C15 C10 -1.1(5) . . . . ?
C13 C14 C15 C16 179.5(4) . . . . ?
C14 C15 C16 C17 179.4(3) . . . . ?
C15 C10 C11 C12 -0.6(5) . . . . ?
C15 C16 C17 C8 0.0(5) . . . . ?
C17 C8 C9 C10 -1.0(5) . . . . ?


#==END

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/hexane'
####################################################################### 
# 
# 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_55
_database_code_depnum_ccdc_archive 'CCDC 2395572'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2025-01-14 deposited with the CCDC.	2025-03-06 downloaded from the CCDC.
;
_audit_creation_date             2024-07-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
# start Validation Reply Form
_vrf_PLAT340_56                  
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01033 Ang.
RESPONSE: Crystal quality was not as high as ideally, leading to a somewhat
 elevated value of R(int), R1, wR2, and in turn, lower than ideal bond
 precision. Despite this, the structure is unambiguously determined.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        
'dimethyl ((2R,3R)-3-(benzo[b]thiophen-3-yl)-4-oxo-2-phenyloxetan-2-yl)phosphonate'
_chemical_formula_moiety         'C19 H17 O5 P S'
_chemical_formula_sum            'C19 H17 O5 P S'
_chemical_formula_weight         388.35
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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 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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        P21
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.3633(5)
_cell_length_b                   7.8457(3)
_cell_length_c                   12.0190(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.666(6)
_cell_angle_gamma                90
_cell_volume                     914.35(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14427
_cell_measurement_temperature    125
_cell_measurement_theta_max      74.0400
_cell_measurement_theta_min      3.9080
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.677
_exptl_absorpt_coefficient_mu    2.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1138
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33520
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.194
_diffrn_reflns_theta_min         3.931
_diffrn_ambient_temperature      125
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P200K'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  89.00   0.50    1.56    --    0.00  32.00  74.00  356
  2  ω   -186.00  -8.00   0.50    6.23    --  -97.10  32.00  74.00  356
  3  ω    -84.00  94.00   0.50    1.56    --    5.00  32.00  74.00  356
  4  ω   -121.00  57.00   0.50    1.56    --  -32.00  44.00 -24.61  356
  5  ω   -129.00  49.00   0.50    1.56    --  -40.00  53.00 118.08  356
  6  ω   -129.00  49.00   0.50    1.56    --  -40.00  55.00-133.01  356
  7  ω   -129.00  49.00   0.50    1.56    --  -40.00  53.00 118.08  356
  8  ω   -133.00  45.00   0.50    1.56    --  -44.00  55.00 -40.61  356
  9  ω   -137.00  41.00   0.50    1.56    --  -48.00  55.00-161.17  356
 10  ω   -141.00  37.00   0.50    6.23    --  -52.00  55.00  54.06  356
 11  ω   -141.00  37.00   0.50    6.23    --  -52.00  55.00 -51.74  356
 12  ω   -145.00  33.00   0.50    6.23    --  -56.00  54.00-125.08  356
 13  ω   -145.00  33.00   0.50    6.23    --  -56.00  55.00  91.96  356
 14  ω   -145.00  33.00   0.50    6.23    --  -56.00  55.00 132.59  356
 15  ω   -131.00  29.00   0.50    6.23    --  -60.00  55.00  17.55  320
 16  ω     -2.00  25.00   0.50    6.23    --  -64.00  55.00 -54.26   54
 17  ω    -34.00  25.00   0.50    6.23    --  -64.00  54.00-121.86  118
 18  ω   -119.00 -50.00   0.50    6.23    --  -64.00  54.00-121.86  138
 19  ω     -8.00  20.00   0.50    6.23    --  -68.00  53.00  72.49   56
 20  ω     -5.00  21.00   0.50    6.23    --  -68.00  55.00 -12.07   52
 21  ω     -8.00  20.00   0.50    6.23    --  -68.00  55.00-154.64   56
 22  ω    -11.00  21.00   0.50    6.23    --  -68.00  52.00 -76.59   64
 23  ω    -15.00  14.00   0.50    6.23    --  -72.00  55.00 148.21   58
 24  ω   -118.00 -92.00   0.50    6.23    --  -72.00  55.00 148.21   52
 25  ω    -13.00  13.00   0.50    6.23    --  -76.00  55.00 118.57   52
 26  ω    -22.00   9.00   0.50    6.23    --  -80.00  55.00 179.76   62
 27  ω    -25.00   8.00   0.50    6.23    --  -80.00  51.00  70.75   66
 28  ω   -160.00 -56.00   0.50    6.23    --  -80.00  55.00 179.76  208
 29  ω   -172.00   4.00   0.50    6.23    --  -84.00  49.00 -92.42  352
 30  ω   -110.00 -46.00   0.50    6.23    --  -88.00  55.00   2.95  128
 31  ω   -172.00-146.00   0.50    6.23    --  -88.00  55.00   2.95   52
 32  ω    -42.00  -1.00   0.50    6.23    --  -88.00  55.00   2.95   82
 33  ω    -33.00  -4.00   0.50    6.23    --  -92.00  55.00  76.94   58
 34  ω   -118.00 -79.00   0.50    6.23    --  -92.00  55.00  76.94   78
 35  ω   -181.00-123.00   0.50    6.23    --  -92.00  55.00  76.94  116
 36  ω   -132.00  -8.00   0.50    6.23    --  -96.00  54.00 -40.49  248
 37  ω   -169.00 -11.00   0.50    6.23    --  -96.00  54.00-167.29  316
 38  ω   -170.00 -12.00   0.50    6.23    --  -97.10  46.00  60.00  316
 39  ω   -180.00  -8.00   0.50    6.23    --  -97.10  55.00 -53.80  344
 40  ω   -124.00 -11.00   0.50    6.23    --  -97.10  46.00-150.00  226
 41  ω    -36.00  -9.00   0.50    6.23    --  -97.10  53.00  -7.06   54
 42  ω    -55.00 -11.00   0.50    6.23    --  -97.10  53.00-103.96   88
 43  ω   -117.00  -8.00   0.50    6.23    --  -97.10  46.00  30.00  218
 44  ω    -99.00 -64.00   0.50    6.23    --  -97.10  53.00-103.96   70
 45  ω   -184.00-158.00   0.50    6.23    --  -97.10  53.00-103.96   52
 46  ω    -73.00  -8.00   0.50    6.23    --  -97.10  55.00 122.97  130
 47  ω   -168.00 -10.00   0.50    6.23    --  -97.10  53.00 139.12  316
 48  ω   -101.00 -76.00   0.50    6.23    --  -97.10  55.00 122.97   50
;
_diffrn_measurement_device       'AFC11: Quarter χ 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0930665000
_diffrn_orient_matrix_UB_12      0.0517180000
_diffrn_orient_matrix_UB_13      -0.0698819000
_diffrn_orient_matrix_UB_21      -0.0261282000
_diffrn_orient_matrix_UB_22      0.1893952000
_diffrn_orient_matrix_UB_23      0.0184971000
_diffrn_orient_matrix_UB_31      0.1261061000
_diffrn_orient_matrix_UB_32      0.0009882000
_diffrn_orient_matrix_UB_33      0.1163983000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                3089
_reflns_number_total             3660
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 1166 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(2)
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3660
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0621
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0989P)²+0.3599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.1855
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S16 S 0.0980(2) 0.9085(2) 0.8321(2) 0.0750(6) Uani 1 1 d . . . . .
P1 P 0.41787(16) 0.2802(2) 0.70450(14) 0.0501(4) Uani 1 1 d . . . . .
O1 O 0.3092(5) 0.1742(6) 0.7190(4) 0.0575(11) Uani 1 1 d . . . . .
O2 O 0.5679(5) 0.2564(6) 0.7967(4) 0.0576(11) Uani 1 1 d . . . . .
O3 O 0.4387(4) 0.2631(6) 0.5823(4) 0.0573(11) Uani 1 1 d . . . . .
O5 O 0.5212(4) 0.6037(6) 0.7587(4) 0.0538(11) Uani 1 1 d . . . . .
O6 O 0.5970(5) 0.7287(6) 0.9415(4) 0.0656(13) Uani 1 1 d . . . . .
C2 C 0.6345(9) 0.0927(10) 0.8097(8) 0.074(2) Uani 1 1 d . . . . .
H2A H 0.644659 0.060520 0.734397 0.111 Uiso 1 1 calc R U . . .
H2B H 0.578478 0.007183 0.831160 0.111 Uiso 1 1 calc R U . . .
H2C H 0.725742 0.099103 0.872278 0.111 Uiso 1 1 calc R U . . .
C3 C 0.3219(9) 0.2210(12) 0.4722(7) 0.075(2) Uani 1 1 d . . . . .
H3A H 0.355765 0.154640 0.419108 0.112 Uiso 1 1 calc R U . . .
H3B H 0.279353 0.326563 0.432376 0.112 Uiso 1 1 calc R U . . .
H3C H 0.253406 0.154083 0.492408 0.112 Uiso 1 1 calc R U . . .
C4 C 0.3904(6) 0.5063(8) 0.7260(5) 0.0473(13) Uani 1 1 d . . . . .
C6 C 0.5157(7) 0.6439(8) 0.8674(6) 0.0540(15) Uani 1 1 d . . . . .
C7 C 0.3815(6) 0.5497(8) 0.8509(5) 0.0480(13) Uani 1 1 d . . . . .
H7 H 0.396172 0.447031 0.903226 0.058 Uiso 1 1 calc R U . . .
C8 C 0.2808(6) 0.5771(8) 0.6154(5) 0.0487(13) Uani 1 1 d . . . . .
C9 C 0.1473(7) 0.5173(10) 0.5836(6) 0.0586(16) Uani 1 1 d . . . . .
H9 H 0.124245 0.438823 0.633775 0.070 Uiso 1 1 calc R U . . .
C10 C 0.0469(8) 0.5708(11) 0.4792(6) 0.0650(18) Uani 1 1 d . . . . .
H10 H -0.045069 0.530486 0.457933 0.078 Uiso 1 1 calc R U . . .
C11 C 0.0822(9) 0.6843(11) 0.4059(6) 0.069(2) Uani 1 1 d . . . . .
H11 H 0.014978 0.719015 0.332548 0.082 Uiso 1 1 calc R U . . .
C12 C 0.2134(10) 0.7458(10) 0.4393(6) 0.071(2) Uani 1 1 d . . . . .
H12 H 0.235879 0.825982 0.389740 0.085 Uiso 1 1 calc R U . . .
C13 C 0.3147(8) 0.6938(9) 0.5439(6) 0.0573(16) Uani 1 1 d . . . . .
H13 H 0.405790 0.737572 0.566240 0.069 Uiso 1 1 calc R U . . .
C14 C 0.2638(6) 0.6549(8) 0.8536(5) 0.0481(13) Uani 1 1 d . . . . .
C15 C 0.2540(9) 0.8263(9) 0.8384(7) 0.0639(19) Uani 1 1 d . . . . .
H15 H 0.326641 0.894534 0.831829 0.077 Uiso 1 1 calc R U . . .
C17 C 0.0366(8) 0.7075(9) 0.8480(6) 0.0585(16) Uani 1 1 d . . . . .
C18 C -0.0923(8) 0.6665(12) 0.8504(6) 0.069(2) Uani 1 1 d . . . . .
H18 H -0.159384 0.752726 0.842326 0.082 Uiso 1 1 calc R U . . .
C19 C -0.1219(7) 0.4972(11) 0.8647(7) 0.0660(19) Uani 1 1 d . . . . .
H19 H -0.210460 0.466135 0.864850 0.079 Uiso 1 1 calc R U . . .
C20 C -0.0198(7) 0.3711(9) 0.8791(6) 0.0551(15) Uani 1 1 d . . . . .
H20 H -0.039805 0.255972 0.891355 0.066 Uiso 1 1 calc R U . . .
C21 C 0.1066(7) 0.4113(9) 0.8758(5) 0.0504(14) Uani 1 1 d . . . . .
H21 H 0.173600 0.324754 0.884523 0.060 Uiso 1 1 calc R U . . .
C22 C 0.1372(6) 0.5831(8) 0.8593(5) 0.0467(13) 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
S16 C15 1.717(8) . ?
S16 C17 1.736(8) . ?
P1 O1 1.459(5) . ?
P1 O2 1.570(5) . ?
P1 O3 1.563(5) . ?
P1 C4 1.829(7) . ?
O2 C2 1.440(9) . ?
O3 C3 1.481(8) . ?
O5 C4 1.483(7) . ?
O5 C6 1.365(8) . ?
O6 C6 1.190(7) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C7 1.573(8) . ?
C4 C8 1.517(8) . ?
C6 C7 1.525(9) . ?
C7 H7 1.0000 . ?
C7 C14 1.482(9) . ?
C8 C9 1.381(9) . ?
C8 C13 1.383(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(12) . ?
C11 H11 0.9500 . ?
C11 C12 1.363(12) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.355(9) . ?
C14 C22 1.451(9) . ?
C15 H15 0.9500 . ?
C17 C18 1.384(11) . ?
C17 C22 1.400(9) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(13) . ?
C19 H19 0.9500 . ?
C19 C20 1.414(10) . ?
C20 H20 0.9500 . ?
C20 C21 1.361(9) . ?
C21 H21 0.9500 . ?
C21 C22 1.415(9) . ?

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
C15 S16 C17 91.7(3) . . ?
O1 P1 O2 117.5(3) . . ?
O1 P1 O3 115.6(3) . . ?
O1 P1 C4 111.8(3) . . ?
O2 P1 C4 100.4(3) . . ?
O3 P1 O2 102.8(3) . . ?
O3 P1 C4 107.2(3) . . ?
C2 O2 P1 120.0(5) . . ?
C3 O3 P1 121.2(4) . . ?
C6 O5 C4 91.7(4) . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O3 C3 H3A 109.5 . . ?
O3 C3 H3B 109.5 . . ?
O3 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O5 C4 P1 111.3(4) . . ?
O5 C4 C7 89.5(4) . . ?
O5 C4 C8 112.0(5) . . ?
C7 C4 P1 114.1(4) . . ?
C8 C4 P1 109.7(4) . . ?
C8 C4 C7 118.6(5) . . ?
O5 C6 C7 96.2(5) . . ?
O6 C6 O5 126.0(6) . . ?
O6 C6 C7 137.8(6) . . ?
C4 C7 H7 112.3 . . ?
C6 C7 C4 82.6(5) . . ?
C6 C7 H7 112.3 . . ?
C14 C7 C4 117.9(5) . . ?
C14 C7 C6 116.5(5) . . ?
C14 C7 H7 112.3 . . ?
C9 C8 C4 119.1(6) . . ?
C9 C8 C13 120.1(6) . . ?
C13 C8 C4 120.7(6) . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.5(7) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.2(7) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.9(6) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.4(7) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C12 118.8(7) . . ?
C8 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C15 C14 C7 125.0(7) . . ?
C15 C14 C22 111.4(6) . . ?
C22 C14 C7 123.3(5) . . ?
S16 C15 H15 123.1 . . ?
C14 C15 S16 113.8(6) . . ?
C14 C15 H15 123.1 . . ?
C18 C17 S16 127.4(6) . . ?
C18 C17 C22 121.8(7) . . ?
C22 C17 S16 110.8(6) . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.8(7) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.8(7) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.4(7) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.4(6) . . ?
C22 C21 H21 120.3 . . ?
C17 C22 C14 112.3(6) . . ?
C17 C22 C21 118.8(6) . . ?
C21 C22 C14 128.9(6) . . ?

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
S16 C17 C18 C19 -179.6(5) . . . . ?
S16 C17 C22 C14 -0.5(7) . . . . ?
S16 C17 C22 C21 178.6(5) . . . . ?
P1 C4 C7 C6 113.5(4) . . . . ?
P1 C4 C7 C14 -130.4(5) . . . . ?
P1 C4 C8 C9 65.5(7) . . . . ?
P1 C4 C8 C13 -111.5(6) . . . . ?
O1 P1 O2 C2 59.3(6) . . . . ?
O1 P1 O3 C3 30.4(6) . . . . ?
O1 P1 C4 O5 157.5(4) . . . . ?
O1 P1 C4 C7 57.9(5) . . . . ?
O1 P1 C4 C8 -78.0(5) . . . . ?
O2 P1 O3 C3 159.7(6) . . . . ?
O2 P1 C4 O5 32.1(5) . . . . ?
O2 P1 C4 C7 -67.5(5) . . . . ?
O2 P1 C4 C8 156.7(4) . . . . ?
O3 P1 O2 C2 -68.8(6) . . . . ?
O3 P1 C4 O5 -75.0(4) . . . . ?
O3 P1 C4 C7 -174.5(4) . . . . ?
O3 P1 C4 C8 49.6(5) . . . . ?
O5 C4 C7 C6 0.2(4) . . . . ?
O5 C4 C7 C14 116.4(5) . . . . ?
O5 C4 C8 C9 -170.3(6) . . . . ?
O5 C4 C8 C13 12.7(8) . . . . ?
O5 C6 C7 C4 -0.2(5) . . . . ?
O5 C6 C7 C14 -117.7(5) . . . . ?
O6 C6 C7 C4 178.9(9) . . . . ?
O6 C6 C7 C14 61.4(11) . . . . ?
C4 P1 O2 C2 -179.3(6) . . . . ?
C4 P1 O3 C3 -94.9(6) . . . . ?
C4 O5 C6 O6 -179.0(7) . . . . ?
C4 O5 C6 C7 0.2(5) . . . . ?
C4 C7 C14 C15 -77.7(9) . . . . ?
C4 C7 C14 C22 94.9(7) . . . . ?
C4 C8 C9 C10 -175.8(6) . . . . ?
C4 C8 C13 C12 175.4(6) . . . . ?
C6 O5 C4 P1 -116.1(4) . . . . ?
C6 O5 C4 C7 -0.2(5) . . . . ?
C6 O5 C4 C8 120.6(5) . . . . ?
C6 C7 C14 C15 18.1(9) . . . . ?
C6 C7 C14 C22 -169.3(5) . . . . ?
C7 C4 C8 C9 -68.2(8) . . . . ?
C7 C4 C8 C13 114.9(7) . . . . ?
C7 C14 C15 S16 174.0(5) . . . . ?
C7 C14 C22 C17 -173.6(5) . . . . ?
C7 C14 C22 C21 7.4(10) . . . . ?
C8 C4 C7 C6 -114.8(6) . . . . ?
C8 C4 C7 C14 1.3(8) . . . . ?
C8 C9 C10 C11 0.7(11) . . . . ?
C9 C8 C13 C12 -1.5(10) . . . . ?
C9 C10 C11 C12 -2.2(12) . . . . ?
C10 C11 C12 C13 1.9(12) . . . . ?
C11 C12 C13 C8 0.0(11) . . . . ?
C13 C8 C9 C10 1.2(10) . . . . ?
C15 S16 C17 C18 -179.4(6) . . . . ?
C15 S16 C17 C22 0.8(5) . . . . ?
C15 C14 C22 C17 -0.1(8) . . . . ?
C15 C14 C22 C21 -179.1(6) . . . . ?
C17 S16 C15 C14 -0.9(6) . . . . ?
C17 C18 C19 C20 1.4(11) . . . . ?
C18 C17 C22 C14 179.6(6) . . . . ?
C18 C17 C22 C21 -1.2(9) . . . . ?
C18 C19 C20 C21 -1.9(10) . . . . ?
C19 C20 C21 C22 0.9(9) . . . . ?
C20 C21 C22 C14 179.6(6) . . . . ?
C20 C21 C22 C17 0.7(9) . . . . ?
C22 C14 C15 S16 0.7(8) . . . . ?
C22 C17 C18 C19 0.2(10) . . . . ?


#==END

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methyl tert-butyl ether/hexane'
