# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_test1
_database_code_depnum_ccdc_archive 'CCDC 2212310'
loop_
_audit_author_name
_audit_author_address
'matyas czugler'
;Retired, from HungAcadSci and Budapest Univ Technol
Hungary
;
_audit_update_record             
;
2022-10-11 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
'diethyl (phenyl(propionamido)methyl)phosphonate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 N O4 P'
_chemical_formula_sum            'C14 H22 N O4 P'
_chemical_formula_weight         299.29

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2778(2)
_cell_length_b                   10.1592(4)
_cell_length_c                   10.8460(4)
_cell_angle_alpha                91.681(3)
_cell_angle_beta                 102.741(3)
_cell_angle_gamma                101.624(3)
_cell_volume                     763.84(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4518
_cell_measurement_theta_min      2.6860
_cell_measurement_theta_max      32.2390

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.192
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95795
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            13665
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.053
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3790
_reflns_number_gt                3188
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0613P)²+0.1897P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3790
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P -0.22691(5) -0.06988(3) 0.28004(3) 0.01796(11) Uani 1 1 d . . . . .
O2 O -0.36027(13) -0.02771(10) 0.15990(9) 0.0201(2) Uani 1 1 d . . . . .
O1 O -0.28247(14) -0.22805(10) 0.27747(9) 0.0225(2) Uani 1 1 d . . . . .
C5 C 0.01062(18) -0.03042(13) 0.24452(12) 0.0179(3) Uani 1 1 d . . . . .
H5 H 0.0015(2) -0.0747(8) 0.1660(14) 0.021 Uiso 1 1 calc R U . . .
O4 O 0.18039(15) -0.24565(11) 0.20212(9) 0.0272(2) Uani 1 1 d . . . . .
N1 N 0.14197(16) -0.08618(12) 0.33972(11) 0.0192(2) Uani 1 1 d . . . . .
H1 H 0.162(3) -0.0602(18) 0.4140(18) 0.026(4) Uiso 1 1 d . . . . .
C12 C 0.21142(19) -0.19446(14) 0.31067(13) 0.0200(3) Uani 1 1 d . . . . .
O3 O -0.23447(14) -0.00806(11) 0.40222(9) 0.0241(2) Uani 1 1 d . . . . .
C13 C 0.3252(2) -0.24931(15) 0.42401(14) 0.0248(3) Uani 1 1 d . . . . .
H13A H 0.4037(11) -0.1757(10) 0.4822(8) 0.030 Uiso 1 1 calc R U . . .
H13B H 0.4093(11) -0.2999(7) 0.3966(4) 0.030 Uiso 1 1 calc R U . . .
C6 C 0.07397(18) 0.11969(13) 0.23364(12) 0.0186(3) Uani 1 1 d . . . . .
C8 C 0.0677(2) 0.31149(15) 0.10613(14) 0.0247(3) Uani 1 1 d . . . . .
H8 H 0.0283(8) 0.3467(7) 0.0271(15) 0.030 Uiso 1 1 calc R U . . .
C3 C -0.50797(19) 0.04858(14) 0.16954(14) 0.0227(3) Uani 1 1 d . . . . .
H3A H -0.5387(5) 0.03951(19) 0.2501(10) 0.027 Uiso 1 1 calc R U . . .
H3B H -0.6220(15) 0.0135(5) 0.1060(8) 0.027 Uiso 1 1 calc R U . . .
C1 C -0.3486(2) -0.31241(14) 0.15843(14) 0.0265(3) Uani 1 1 d . . . . .
H1A H -0.2850(8) -0.2709(5) 0.0947(8) 0.032 Uiso 1 1 calc R U . . .
H1B H -0.4873(18) -0.32232(19) 0.1274(4) 0.032 Uiso 1 1 calc R U . . .
C11 C 0.1797(2) 0.20667(14) 0.33821(13) 0.0230(3) Uani 1 1 d . . . . .
H11 H 0.2184(7) 0.1711(7) 0.4197(15) 0.028 Uiso 1 1 calc R U . . .
C10 C 0.2300(2) 0.34440(15) 0.32608(15) 0.0275(3) Uani 1 1 d . . . . .
H10 H 0.2993(15) 0.3993(12) 0.3932(15) 0.033 Uiso 1 1 calc R U . . .
C7 C 0.01954(19) 0.17328(15) 0.11758(13) 0.0216(3) Uani 1 1 d . . . . .
H7 H -0.0494(13) 0.1164(11) 0.0474(14) 0.026 Uiso 1 1 calc R U . . .
C9 C 0.1734(2) 0.39738(15) 0.21052(15) 0.0277(3) Uani 1 1 d . . . . .
H9 H 0.2059(7) 0.489(2) 0.2033(2) 0.033 Uiso 1 1 calc R U . . .
C4 C -0.4367(2) 0.19403(15) 0.15328(15) 0.0271(3) Uani 1 1 d . . . . .
H4A H -0.3268(17) 0.2307(5) 0.2207(10) 0.041 Uiso 1 1 calc R U . . .
H4B H -0.5368(12) 0.2421(6) 0.1552(11) 0.041 Uiso 1 1 calc R U . . .
H4C H -0.4007(16) 0.2026(2) 0.0735(10) 0.041 Uiso 1 1 calc R U . . .
C14 C 0.1908(2) -0.33989(17) 0.49116(15) 0.0330(4) Uani 1 1 d . . . . .
H14A H 0.1136(16) -0.2871(7) 0.5250(11) 0.050 Uiso 1 1 calc R U . . .
H14B H 0.2664(9) -0.3789(11) 0.5598(11) 0.050 Uiso 1 1 calc R U . . .
H14C H 0.1068(16) -0.4113(11) 0.4314(8) 0.050 Uiso 1 1 calc R U . . .
C2 C -0.3010(3) -0.44770(16) 0.18192(18) 0.0385(4) Uani 1 1 d . . . . .
H2A H -0.1618(17) -0.4367(2) 0.2142(13) 0.058 Uiso 1 1 calc R U . . .
H2B H -0.3420(18) -0.5051(8) 0.1026(10) 0.058 Uiso 1 1 calc R U . . .
H2C H -0.3680(17) -0.4896(8) 0.2444(12) 0.058 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 O3 1.4666(10) . ?
P1 O2 1.5703(10) . ?
P1 O1 1.5738(10) . ?
P1 C5 1.8224(13) . ?
O2 C3 1.4655(16) . ?
O1 C1 1.4587(17) . ?
C5 N1 1.4553(16) . ?
C5 C6 1.5176(18) . ?
C5 H5 0.934(17) . ?
O4 C12 1.2276(17) . ?
N1 C12 1.3560(17) . ?
N1 H1 0.813(19) . ?
C12 C13 1.5115(19) . ?
C13 C14 1.525(2) . ?
C13 H13A 0.962(12) . ?
C13 H13B 0.962(12) . ?
C6 C11 1.3935(19) . ?
C6 C7 1.3946(18) . ?
C8 C9 1.387(2) . ?
C8 C7 1.393(2) . ?
C8 H8 0.946(18) . ?
C3 C4 1.493(2) . ?
C3 H3A 0.951(12) . ?
C3 H3B 0.951(12) . ?
C1 C2 1.499(2) . ?
C1 H1A 0.975(12) . ?
C1 H1B 0.975(12) . ?
C11 C10 1.391(2) . ?
C11 H11 0.970(18) . ?
C10 C9 1.390(2) . ?
C10 H10 0.892(19) . ?
C7 H7 0.924(18) . ?
C9 H9 0.919(19) . ?
C4 H4A 0.959(11) . ?
C4 H4B 0.959(11) . ?
C4 H4C 0.959(11) . ?
C14 H14A 0.969(12) . ?
C14 H14B 0.969(12) . ?
C14 H14C 0.969(12) . ?
C2 H2A 0.978(12) . ?
C2 H2B 0.978(12) . ?
C2 H2C 0.978(12) . ?

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
O3 P1 O2 115.78(6) . . ?
O3 P1 O1 110.54(6) . . ?
O2 P1 O1 106.99(5) . . ?
O3 P1 C5 113.99(6) . . ?
O2 P1 C5 102.93(5) . . ?
O1 P1 C5 105.82(6) . . ?
C3 O2 P1 122.17(8) . . ?
C1 O1 P1 121.59(9) . . ?
N1 C5 C6 114.46(11) . . ?
N1 C5 P1 107.94(8) . . ?
C6 C5 P1 110.94(9) . . ?
N1 C5 H5 107.8 . . ?
C6 C5 H5 107.8 . . ?
P1 C5 H5 107.8 . . ?
C12 N1 C5 121.46(11) . . ?
C12 N1 H1 118.0(13) . . ?
C5 N1 H1 119.9(13) . . ?
O4 C12 N1 122.91(12) . . ?
O4 C12 C13 122.88(12) . . ?
N1 C12 C13 114.18(12) . . ?
C12 C13 C14 110.80(12) . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C11 C6 C7 118.86(13) . . ?
C11 C6 C5 121.57(12) . . ?
C7 C6 C5 119.53(12) . . ?
C9 C8 C7 119.98(13) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
O2 C3 C4 110.15(11) . . ?
O2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
O2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
O1 C1 C2 108.36(12) . . ?
O1 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
O1 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
C10 C11 C6 120.18(13) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C9 C10 C11 120.69(14) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C8 C7 C6 120.83(13) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C8 C9 C10 119.45(14) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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
O3 P1 O2 C3 -10.65(12) . . . . ?
O1 P1 O2 C3 113.06(10) . . . . ?
C5 P1 O2 C3 -135.68(10) . . . . ?
O3 P1 O1 C1 159.28(10) . . . . ?
O2 P1 O1 C1 32.40(11) . . . . ?
C5 P1 O1 C1 -76.85(11) . . . . ?
O3 P1 C5 N1 63.22(10) . . . . ?
O2 P1 C5 N1 -170.59(8) . . . . ?
O1 P1 C5 N1 -58.46(10) . . . . ?
O3 P1 C5 C6 -62.92(10) . . . . ?
O2 P1 C5 C6 63.27(10) . . . . ?
O1 P1 C5 C6 175.40(8) . . . . ?
C6 C5 N1 C12 -126.94(13) . . . . ?
P1 C5 N1 C12 109.02(12) . . . . ?
C5 N1 C12 O4 5.5(2) . . . . ?
C5 N1 C12 C13 -172.67(11) . . . . ?
O4 C12 C13 C14 -97.03(16) . . . . ?
N1 C12 C13 C14 81.19(15) . . . . ?
N1 C5 C6 C11 -31.50(17) . . . . ?
P1 C5 C6 C11 90.92(13) . . . . ?
N1 C5 C6 C7 150.90(12) . . . . ?
P1 C5 C6 C7 -86.68(13) . . . . ?
P1 O2 C3 C4 100.63(12) . . . . ?
P1 O1 C1 C2 153.55(11) . . . . ?
C7 C6 C11 C10 -0.2(2) . . . . ?
C5 C6 C11 C10 -177.80(12) . . . . ?
C6 C11 C10 C9 0.9(2) . . . . ?
C9 C8 C7 C6 0.9(2) . . . . ?
C11 C6 C7 C8 -0.73(19) . . . . ?
C5 C6 C7 C8 176.94(11) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C11 C10 C9 C8 -0.7(2) . . . . ?

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.060


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane : methanol 0.97 : 0.03'
