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#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/30/7203081.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_7203081
loop_
_publ_author_name
'Zhang, Jianfeng'
'Cui, Zhanwei'
'Wang, Fei'
'Wang, Yadan'
'Miao, Zhiwei'
'Chen, Ruyu'
_publ_section_title
;
 Mannich type reactions of chlorophosphites, phosphoramides and
 aldehydes (ketones) under solvent-free and catalyst-free
 conditions---synthesis of N-phosphoramino α-aminophosphonates
;
_journal_issue                   12
_journal_name_full               'Green Chemistry'
_journal_page_first              1341
_journal_paper_doi               10.1039/b710008f
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C16 H27 N O7 P2'
_chemical_formula_sum            'C16 H27 N O7 P2'
_chemical_formula_weight         407.33
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.689(9)
_cell_angle_beta                 98.771(7)
_cell_angle_gamma                111.382(16)
_cell_formula_units_Z            2
_cell_length_a                   9.955(9)
_cell_length_b                   10.404(9)
_cell_length_c                   10.839(9)
_cell_measurement_reflns_used    2306
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.6
_cell_volume                     1011.0(15)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10348
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3551
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0632P)²+0.2781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1388
_reflns_number_gt                2931
_reflns_number_total             3551
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b710008f.txt
_cod_data_source_block           shelxl
_cod_database_code               7203081
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.32939(9) 0.40280(8) 0.15140(7) 0.0227(2) Uani 1 1 d . . .
P2 P 0.71709(9) 0.38095(8) 0.25502(7) 0.0226(2) Uani 1 1 d . . .
O1 O 0.3172(2) 0.4513(2) 0.03069(19) 0.0293(5) Uani 1 1 d . . .
O2 O 0.2109(2) 0.4188(2) 0.22605(18) 0.0246(5) Uani 1 1 d . . .
O3 O 0.3018(2) 0.2404(2) 0.12769(19) 0.0282(5) Uani 1 1 d . . .
O4 O 0.6432(2) 0.2840(2) 0.33408(18) 0.0248(5) Uani 1 1 d . . .
O5 O 0.8708(2) 0.4905(2) 0.33767(19) 0.0300(5) Uani 1 1 d . . .
O6 O 0.7647(2) 0.3160(2) 0.13907(19) 0.0292(5) Uani 1 1 d . . .
O7 O 0.4363(2) 0.6199(2) 0.4651(2) 0.0285(5) Uani 1 1 d . . .
H7 H 0.410(4) 0.660(4) 0.531(3) 0.043 Uiso 1 1 d . . .
N1 N 0.6169(3) 0.4596(3) 0.1943(2) 0.0224(6) Uani 1 1 d D . .
H1 H 0.633(3) 0.483(3) 0.1233(17) 0.034 Uiso 1 1 d D . .
C1 C 0.1680(3) 0.3334(3) 0.3214(3) 0.0282(7) Uani 1 1 d . . .
H1A H 0.0836 0.3469 0.3506 0.034 Uiso 1 1 calc R . .
H1B H 0.2515 0.3653 0.3962 0.034 Uiso 1 1 calc R . .
C2 C 0.1245(3) 0.1772(3) 0.2672(3) 0.0303(8) Uani 1 1 d . . .
C3 C 0.2568(4) 0.1598(3) 0.2254(3) 0.0326(8) Uani 1 1 d . . .
H3A H 0.3404 0.1920 0.3002 0.039 Uiso 1 1 calc R . .
H3B H 0.2314 0.0587 0.1914 0.039 Uiso 1 1 calc R . .
C4 C -0.0083(3) 0.1232(3) 0.1539(3) 0.0366(8) Uani 1 1 d . . .
H4A H 0.0200 0.1705 0.0839 0.055 Uiso 1 1 calc R . .
H4B H -0.0898 0.1434 0.1801 0.055 Uiso 1 1 calc R . .
H4C H -0.0401 0.0212 0.1252 0.055 Uiso 1 1 calc R . .
C5 C 0.0871(4) 0.0955(4) 0.3735(3) 0.0415(9) Uani 1 1 d . . .
H5A H 0.0674 -0.0039 0.3425 0.062 Uiso 1 1 calc R . .
H5B H -0.0007 0.1030 0.3987 0.062 Uiso 1 1 calc R . .
H5C H 0.1707 0.1352 0.4473 0.062 Uiso 1 1 calc R . .
C6 C 0.5107(3) 0.4962(3) 0.2565(3) 0.0217(7) Uani 1 1 d . . .
H6 H 0.5092 0.4603 0.3376 0.026 Uiso 1 1 calc R . .
C7 C 0.5487(3) 0.6543(3) 0.2891(3) 0.0215(6) Uani 1 1 d . . .
C8 C 0.5075(3) 0.7106(3) 0.3945(3) 0.0218(6) Uani 1 1 d . . .
C9 C 0.5409(3) 0.8550(3) 0.4259(3) 0.0282(7) Uani 1 1 d . . .
H9 H 0.5132 0.8924 0.4981 0.034 Uiso 1 1 calc R . .
C10 C 0.6148(3) 0.9446(3) 0.3512(3) 0.0296(7) Uani 1 1 d . . .
H10 H 0.6377 1.0429 0.3723 0.036 Uiso 1 1 calc R . .
C11 C 0.6545(3) 0.8891(3) 0.2463(3) 0.0315(8) Uani 1 1 d . . .
H11 H 0.7038 0.9495 0.1946 0.038 Uiso 1 1 calc R . .
C12 C 0.6228(3) 0.7452(3) 0.2159(3) 0.0256(7) Uani 1 1 d . . .
H12 H 0.6521 0.7086 0.1444 0.031 Uiso 1 1 calc R . .
C13 C 0.9665(4) 0.6004(4) 0.2836(4) 0.0533(11) Uani 1 1 d . . .
H13A H 0.9124 0.6564 0.2509 0.064 Uiso 1 1 calc R . .
H13B H 0.9966 0.5572 0.2114 0.064 Uiso 1 1 calc R . .
C14 C 1.0977(4) 0.6926(4) 0.3815(3) 0.0463(10) Uani 1 1 d . . .
H14A H 1.0675 0.7354 0.4526 0.070 Uiso 1 1 calc R . .
H14B H 1.1616 0.7670 0.3449 0.070 Uiso 1 1 calc R . .
H14C H 1.1520 0.6372 0.4124 0.070 Uiso 1 1 calc R . .
C15 C 0.6591(4) 0.2161(4) 0.0276(3) 0.0393(9) Uani 1 1 d . . .
H15A H 0.5696 0.2374 0.0102 0.047 Uiso 1 1 calc R . .
H15B H 0.6291 0.1188 0.0427 0.047 Uiso 1 1 calc R . .
C16 C 0.7334(5) 0.2299(5) -0.0839(3) 0.0540(11) Uani 1 1 d . . .
H16A H 0.7665 0.3276 -0.0955 0.081 Uiso 1 1 calc R . .
H16B H 0.6632 0.1670 -0.1613 0.081 Uiso 1 1 calc R . .
H16C H 0.8188 0.2040 -0.0674 0.081 Uiso 1 1 calc R . .
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
O1 P1 O2 111.67(12) . . ?
O1 P1 O3 111.28(13) . . ?
O2 P1 O3 106.27(11) . . ?
O1 P1 C6 112.81(13) . . ?
O2 P1 C6 108.08(14) . . ?
O3 P1 C6 106.36(13) . . ?
O4 P2 O6 116.97(13) . . ?
O4 P2 O5 108.81(13) . . ?
O6 P2 O5 101.44(13) . . ?
O4 P2 N1 112.83(13) . . ?
O6 P2 N1 104.85(13) . . ?
O5 P2 N1 111.39(14) . . ?
C1 O2 P1 119.88(18) . . ?
C3 O3 P1 119.58(19) . . ?
C13 O5 P2 120.5(2) . . ?
C15 O6 P2 123.0(2) . . ?
C6 N1 P2 124.0(2) . . ?
O2 C1 C2 111.3(2) . . ?
C3 C2 C1 108.0(2) . . ?
C3 C2 C5 108.9(3) . . ?
C1 C2 C5 108.4(3) . . ?
C3 C2 C4 110.3(3) . . ?
C1 C2 C4 110.7(3) . . ?
C5 C2 C4 110.5(3) . . ?
O3 C3 C2 111.5(2) . . ?
N1 C6 C7 113.6(2) . . ?
N1 C6 P1 107.3(2) . . ?
C7 C6 P1 111.33(19) . . ?
C12 C7 C8 118.6(3) . . ?
C12 C7 C6 121.8(3) . . ?
C8 C7 C6 119.6(2) . . ?
O7 C8 C9 121.9(3) . . ?
O7 C8 C7 117.5(3) . . ?
C9 C8 C7 120.5(3) . . ?
C8 C9 C10 120.1(3) . . ?
C11 C10 C9 119.5(3) . . ?
C10 C11 C12 120.4(3) . . ?
C7 C12 C11 120.9(3) . . ?
O5 C13 C14 109.7(3) . . ?
O6 C15 C16 107.6(3) . . ?
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 1.468(2) . ?
P1 O2 1.572(2) . ?
P1 O3 1.587(2) . ?
P1 C6 1.816(3) . ?
P2 O4 1.475(2) . ?
P2 O6 1.565(2) . ?
P2 O5 1.575(2) . ?
P2 N1 1.623(3) . ?
O2 C1 1.465(3) . ?
O3 C3 1.461(4) . ?
O5 C13 1.454(4) . ?
O6 C15 1.458(4) . ?
O7 C8 1.360(3) . ?
N1 C6 1.470(3) . ?
C1 C2 1.525(4) . ?
C2 C3 1.519(4) . ?
C2 C5 1.533(4) . ?
C2 C4 1.534(4) . ?
C6 C7 1.525(4) . ?
C7 C12 1.391(4) . ?
C7 C8 1.399(4) . ?
C8 C9 1.396(4) . ?
C9 C10 1.396(4) . ?
C10 C11 1.382(4) . ?
C11 C12 1.394(4) . ?
C13 C14 1.464(5) . ?
C15 C16 1.507(5) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.860(10) 1.950(11) 2.808(4) 176(3) 2_665
O7 H7 O4 0.90(4) 1.73(4) 2.624(3) 172(3) 2_666
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 O2 C1 158.0(2) . . . . ?
O3 P1 O2 C1 36.5(2) . . . . ?
C6 P1 O2 C1 -77.3(2) . . . . ?
O1 P1 O3 C3 -158.2(2) . . . . ?
O2 P1 O3 C3 -36.4(2) . . . . ?
C6 P1 O3 C3 78.5(2) . . . . ?
O4 P2 O5 C13 -179.1(3) . . . . ?
O6 P2 O5 C13 57.0(3) . . . . ?
N1 P2 O5 C13 -54.1(3) . . . . ?
O4 P2 O6 C15 67.6(3) . . . . ?
O5 P2 O6 C15 -174.2(2) . . . . ?
N1 P2 O6 C15 -58.2(3) . . . . ?
O4 P2 N1 C6 31.3(3) . . . . ?
O6 P2 N1 C6 159.7(2) . . . . ?
O5 P2 N1 C6 -91.4(2) . . . . ?
P1 O2 C1 C2 -51.5(3) . . . . ?
O2 C1 C2 C3 59.9(3) . . . . ?
O2 C1 C2 C5 177.8(2) . . . . ?
O2 C1 C2 C4 -61.0(3) . . . . ?
P1 O3 C3 C2 51.5(3) . . . . ?
C1 C2 C3 O3 -60.1(3) . . . . ?
C5 C2 C3 O3 -177.6(3) . . . . ?
C4 C2 C3 O3 61.0(3) . . . . ?
P2 N1 C6 C7 117.4(2) . . . . ?
P2 N1 C6 P1 -119.1(2) . . . . ?
O1 P1 C6 N1 -65.9(2) . . . . ?
O2 P1 C6 N1 170.16(17) . . . . ?
O3 P1 C6 N1 56.4(2) . . . . ?
O1 P1 C6 C7 59.1(2) . . . . ?
O2 P1 C6 C7 -64.9(2) . . . . ?
O3 P1 C6 C7 -178.68(18) . . . . ?
N1 C6 C7 C12 30.5(4) . . . . ?
P1 C6 C7 C12 -90.8(3) . . . . ?
N1 C6 C7 C8 -150.0(3) . . . . ?
P1 C6 C7 C8 88.7(3) . . . . ?
C12 C7 C8 O7 -179.5(3) . . . . ?
C6 C7 C8 O7 1.0(4) . . . . ?
C12 C7 C8 C9 -0.4(4) . . . . ?
C6 C7 C8 C9 -179.9(3) . . . . ?
O7 C8 C9 C10 179.7(3) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C9 C10 C11 C12 -0.8(5) . . . . ?
C8 C7 C12 C11 -0.4(4) . . . . ?
C6 C7 C12 C11 179.1(3) . . . . ?
C10 C11 C12 C7 1.0(5) . . . . ?
P2 O5 C13 C14 176.7(2) . . . . ?
P2 O6 C15 C16 153.5(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139195000
