#------------------------------------------------------------------------------
#$Date: 2023-04-13 15:19:33 +0300 (Thu, 13 Apr 2023) $
#$Revision: 282621 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/90/7159082.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7159082
loop_
_publ_author_name
'Varga, Petra Regina'
'Karaghiosoff, Konstantin'
'Sári, Éva Viktória'
'Simon, András'
'Hegedűs, László'
'Drahos, László'
'Keglevich, György'
_publ_section_title
;
 New N-acyl- as well as N-phosphonoylmethyl- and
 N-phosphinoylmethyl-α-amino-benzylphosphonates by acylation and a tandem
 Kabachnik--Fields protocol
;
_journal_issue                   8
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              1709
_journal_page_last               1718
_journal_paper_doi               10.1039/D3OB00010A
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C14 H22 N O4 P'
_chemical_formula_sum            'C14 H22 N O4 P'
_chemical_formula_weight         299.29
_chemical_name_systematic
'diethyl (phenyl(propionamido)methyl)phosphonate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2022-10-11 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                91.681(3)
_cell_angle_beta                 102.741(3)
_cell_angle_gamma                101.624(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2778(2)
_cell_length_b                   10.1592(4)
_cell_length_c                   10.8460(4)
_cell_measurement_reflns_used    4518
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      32.2390
_cell_measurement_theta_min      2.6860
_cell_volume                     763.84(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_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).
;
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13665
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.053
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95795
_exptl_absorpt_correction_type   multi-scan
_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.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane : methanol 0.97 : 0.03'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0390
_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)+(0.0613P)²+0.1897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1072
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3188
_reflns_number_total             3790
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00010a3.cif
_cod_data_source_block           test1
_cod_depositor_comments          'Adding full bibliography for 7159082.cif.'
_cod_database_code               7159082
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2018/1
_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.
;
_shelx_estimated_absorpt_t_min   0.927
_shelx_estimated_absorpt_t_max   0.981
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 . . .
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'
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_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_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) . . . . ?
