#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/63/1516326.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_1516326
loop_
_publ_author_name
'Kim, Yea Rin'
'Cho, Seungyoon'
'Lee, Phil Ho'
_publ_section_title
;
 Metal-Free Azaphosphaannulation of Phosphonamides through Intramolecular
 Oxidative C-N Bond Formation.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              3098
_journal_page_last               3101
_journal_paper_doi               10.1021/ol501207w
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C10 H12 N O3 P'
_chemical_formula_weight         225.18
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.90(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2030(14)
_cell_length_b                   8.5010(17)
_cell_length_c                   17.051(3)
_cell_measurement_reflns_used    1895
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.70
_cell_measurement_theta_min      2.39
_cell_volume                     1044.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5691
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_correction_T_min  0.9519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2050
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0441
_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)+(0.0617P)²+0.1808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1230
_reflns_number_gt                1765
_reflns_number_total             2050
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501207w_si_002.cif
_cod_data_source_block           ye172sadp21c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1516325--1516326.cif.
;
_cod_original_cell_volume        1043.9(4)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1516326
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
P1 P 0.37962(7) 0.83117(5) 0.07830(3) 0.0213(2) Uani 1 1 d .
N1 N 0.3029(2) 0.85107(18) -0.01414(9) 0.0246(4) Uani 1 1 d D
H1N H 0.326(3) 0.9332(16) -0.0417(11) 0.037 Uiso 1 1 d D
O1 O 0.2052(2) 0.70164(17) -0.11994(8) 0.0329(4) Uani 1 1 d .
O2 O 0.57164(19) 0.88374(15) 0.09435(7) 0.0266(3) Uani 1 1 d .
O3 O 0.24639(19) 0.92526(15) 0.13356(8) 0.0277(3) Uani 1 1 d .
C1 C 0.3320(3) 0.6255(2) 0.08021(11) 0.0214(4) Uani 1 1 d .
C2 C 0.3615(3) 0.5168(2) 0.14036(11) 0.0246(4) Uani 1 1 d .
C3 C 0.3142(3) 0.3612(2) 0.12340(12) 0.0284(5) Uani 1 1 d .
H3 H 0.3292 0.2837 0.1631 0.034 Uiso 1 1 calc R
C4 C 0.2455(3) 0.3163(2) 0.04980(13) 0.0297(5) Uani 1 1 d .
H4 H 0.2149 0.2092 0.0405 0.036 Uiso 1 1 calc R
C5 C 0.2211(3) 0.4253(2) -0.01002(12) 0.0268(5) Uani 1 1 d .
H5 H 0.1757 0.3945 -0.0603 0.032 Uiso 1 1 calc R
C6 C 0.2652(2) 0.5798(2) 0.00622(10) 0.0214(4) Uani 1 1 d .
C7 C 0.2516(3) 0.7121(2) -0.05143(11) 0.0233(4) Uani 1 1 d .
C8 C 0.4439(3) 0.5636(3) 0.21831(12) 0.0358(5) Uani 1 1 d .
H8A H 0.5797 0.5605 0.2157 0.054 Uiso 1 1 calc R
H8B H 0.4021 0.4904 0.2588 0.054 Uiso 1 1 calc R
H8C H 0.4039 0.6705 0.2314 0.054 Uiso 1 1 calc R
C9 C 0.0439(3) 0.9070(3) 0.13221(12) 0.0344(5) Uani 1 1 d .
H9A H 0.0041 0.8592 0.0817 0.041 Uiso 1 1 calc R
H9B H -0.0151 1.0118 0.1361 0.041 Uiso 1 1 calc R
C10 C -0.0195(4) 0.8058(3) 0.19819(15) 0.0483(7) Uani 1 1 d .
H10A H 0.0305 0.6994 0.1920 0.072 Uiso 1 1 calc R
H10B H -0.1554 0.8015 0.1978 0.072 Uiso 1 1 calc R
H10C H 0.0250 0.8501 0.2481 0.072 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
O2 P1 O3 108.29(8)
O2 P1 N1 116.07(9)
O3 P1 N1 108.52(8)
O2 P1 C1 118.29(8)
O3 P1 C1 111.62(8)
N1 P1 C1 93.20(8)
C7 N1 P1 115.32(13)
C7 N1 H1N 119.6(15)
P1 N1 H1N 122.2(16)
C9 O3 P1 123.53(12)
C2 C1 C6 121.75(17)
C2 C1 P1 129.53(15)
C6 C1 P1 108.63(13)
C1 C2 C3 116.23(18)
C1 C2 C8 121.97(17)
C3 C2 C8 121.78(18)
C2 C3 C4 121.87(18)
C2 C3 H3 119.1
C4 C3 H3 119.1
C5 C4 C3 121.19(18)
C5 C4 H4 119.4
C3 C4 H4 119.4
C6 C5 C4 117.55(18)
C6 C5 H5 121.2
C4 C5 H5 121.2
C5 C6 C1 121.38(17)
C5 C6 C7 124.89(17)
C1 C6 C7 113.71(16)
O1 C7 N1 124.80(18)
O1 C7 C6 126.26(18)
N1 C7 C6 108.93(16)
C2 C8 H8A 109.5
C2 C8 H8B 109.5
H8A C8 H8B 109.5
C2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O3 C9 C10 111.40(18)
O3 C9 H9A 109.3
C10 C9 H9A 109.3
O3 C9 H9B 109.3
C10 C9 H9B 109.3
H9A C9 H9B 108.0
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O2 1.4750(14)
P1 O3 1.5738(15)
P1 N1 1.6706(17)
P1 C1 1.7825(19)
N1 C7 1.389(2)
N1 H1N 0.860(2)
O1 C7 1.213(2)
O3 C9 1.467(2)
C1 C2 1.394(3)
C1 C6 1.398(3)
C2 C3 1.395(3)
C2 C8 1.501(3)
C3 C4 1.395(3)
C3 H3 0.9500
C4 C5 1.387(3)
C4 H4 0.9500
C5 C6 1.378(3)
C5 H5 0.9500
C6 C7 1.496(3)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C10 1.493(3)
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
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
O2 P1 N1 C7 119.26(15)
O3 P1 N1 C7 -118.57(15)
C1 P1 N1 C7 -4.50(16)
O2 P1 O3 C9 178.16(14)
N1 P1 O3 C9 51.36(16)
C1 P1 O3 C9 -49.94(17)
O2 P1 C1 C2 57.1(2)
O3 P1 C1 C2 -69.5(2)
N1 P1 C1 C2 179.12(19)
O2 P1 C1 C6 -119.34(14)
O3 P1 C1 C6 114.04(13)
N1 P1 C1 C6 2.67(15)
C6 C1 C2 C3 -2.2(3)
P1 C1 C2 C3 -178.27(15)
C6 C1 C2 C8 176.26(18)
P1 C1 C2 C8 0.2(3)
C1 C2 C3 C4 1.5(3)
C8 C2 C3 C4 -177.01(19)
C2 C3 C4 C5 0.0(3)
C3 C4 C5 C6 -0.8(3)
C4 C5 C6 C1 0.0(3)
C4 C5 C6 C7 178.61(17)
C2 C1 C6 C5 1.5(3)
P1 C1 C6 C5 178.32(15)
C2 C1 C6 C7 -177.20(17)
P1 C1 C6 C7 -0.4(2)
P1 N1 C7 O1 -174.56(17)
P1 N1 C7 C6 4.8(2)
C5 C6 C7 O1 -2.0(3)
C1 C6 C7 O1 176.72(19)
C5 C6 C7 N1 178.66(18)
C1 C6 C7 N1 -2.6(2)
P1 O3 C9 C10 101.38(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139043510
