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#$Date: 2025-04-05 06:59:59 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299083 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160248.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_7160248
loop_
_publ_author_name
'Cao, Dingsheng'
'Wan, Jie-Ping'
'Liu, Yunyun'
_publ_section_title
;
 Metal-free hydrodifunctionalization of enaminones for the synthesis of
 ketomethylene-functionalized phosphoryl alcohols.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              799
_journal_page_last               802
_journal_paper_doi               10.1039/d4ob01779j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C21 H19 O3 P'
_chemical_formula_sum            'C21 H19 O3 P'
_chemical_formula_weight         350.33
_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   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2024-10-22 deposited with the CCDC.	2024-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                82.92(3)
_cell_angle_beta                 78.03(3)
_cell_angle_gamma                65.49(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5836(19)
_cell_length_b                   10.090(2)
_cell_length_c                   10.318(2)
_cell_measurement_reflns_used    5702
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     887.3(4)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.0968
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7062
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.064
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.821
_exptl_absorpt_correction_T_min  0.743
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0523
_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)+(0.0515P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1476
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2074
_reflns_number_total             3121
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01779j2.cif
_cod_data_source_block           shx97
_cod_depositor_comments          'Adding full bibliography for 7160248.cif.'
_cod_database_code               7160248
_shelx_shelxl_version_number     2016/6
_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'
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 0.33855(7) 0.17432(6) 0.68649(7) 0.0492(3) Uani 1 1 d . . . . .
O1 O 0.5308(2) 0.4154(2) 0.3405(3) 0.0886(8) Uani 1 1 d . . . . .
O2 O 0.35628(18) 0.22669(17) 0.43037(18) 0.0560(5) Uani 1 1 d . . . . .
H2B H 0.426913 0.153342 0.397448 0.084 Uiso 1 1 calc R U . . .
O3 O 0.4152(2) 0.01303(16) 0.67915(19) 0.0633(6) Uani 1 1 d . . . . .
C1 C 0.8378(4) 0.2750(3) 0.2004(3) 0.0789(10) Uani 1 1 d . . . . .
H1A H 0.762305 0.311425 0.146367 0.095 Uiso 1 1 calc R U . . .
C2 C 0.9924(5) 0.2381(4) 0.1442(5) 0.1011(15) Uani 1 1 d . . . . .
H2A H 1.021564 0.246618 0.052830 0.121 Uiso 1 1 calc R U . . .
C3 C 1.1022(5) 0.1890(4) 0.2250(6) 0.1018(17) Uani 1 1 d . . . . .
H3A H 1.205500 0.170068 0.188571 0.122 Uiso 1 1 calc R U . . .
C4 C 1.0618(4) 0.1672(4) 0.3585(5) 0.0930(13) Uani 1 1 d . . . . .
H4A H 1.137414 0.131106 0.412327 0.112 Uiso 1 1 calc R U . . .
C5 C 0.9069(4) 0.1997(3) 0.4126(4) 0.0723(9) Uani 1 1 d . . . . .
H5A H 0.879585 0.181123 0.502706 0.087 Uiso 1 1 calc R U . . .
C6 C 0.7936(3) 0.2587(3) 0.3355(3) 0.0547(7) Uani 1 1 d . . . . .
C7 C 0.6246(3) 0.3111(3) 0.3907(3) 0.0596(8) Uani 1 1 d . . . . .
C8 C 0.5739(3) 0.2321(3) 0.5146(3) 0.0552(7) Uani 1 1 d . . . . .
H8A H 0.632236 0.127831 0.506535 0.066 Uiso 1 1 calc R U . . .
H8B H 0.597713 0.260385 0.591117 0.066 Uiso 1 1 calc R U . . .
C9 C 0.4021(3) 0.2663(2) 0.5361(3) 0.0499(7) Uani 1 1 d . . . . .
H9A H 0.345093 0.371718 0.545656 0.060 Uiso 1 1 calc R U . . .
C10 C 0.3772(3) 0.2335(3) 0.8274(3) 0.0526(7) Uani 1 1 d . . . . .
C11 C 0.5037(4) 0.1456(4) 0.8832(4) 0.0919(12) Uani 1 1 d . . . . .
H11A H 0.571007 0.057247 0.845610 0.110 Uiso 1 1 calc R U . . .
C12 C 0.5339(4) 0.1856(5) 0.9948(4) 0.0988(12) Uani 1 1 d . . . . .
H12A H 0.620939 0.123499 1.030888 0.119 Uiso 1 1 calc R U . . .
C13 C 0.4394(5) 0.3126(4) 1.0519(4) 0.0840(11) Uani 1 1 d . . . . .
H13A H 0.459237 0.339099 1.127079 0.101 Uiso 1 1 calc R U . . .
C14 C 0.3165(6) 0.3989(4) 0.9967(4) 0.1126(15) Uani 1 1 d . . . . .
H14A H 0.251292 0.487666 1.034519 0.135 Uiso 1 1 calc R U . . .
C15 C 0.2808(4) 0.3629(3) 0.8854(4) 0.0890(11) Uani 1 1 d . . . . .
H15A H 0.192794 0.425727 0.850878 0.107 Uiso 1 1 calc R U . . .
C16 C 0.1301(3) 0.2412(2) 0.7051(3) 0.0504(7) Uani 1 1 d . . . . .
C17 C 0.0606(3) 0.1470(3) 0.7611(3) 0.0599(8) Uani 1 1 d . . . . .
H17A H 0.121768 0.051190 0.783860 0.072 Uiso 1 1 calc R U . . .
C18 C -0.1006(4) 0.1952(3) 0.7834(3) 0.0749(10) Uani 1 1 d . . . . .
H18A H -0.146582 0.131204 0.821149 0.090 Uiso 1 1 calc R U . . .
C19 C -0.1916(3) 0.3346(3) 0.7506(3) 0.0702(9) Uani 1 1 d . . . . .
H19A H -0.299349 0.366286 0.768201 0.084 Uiso 1 1 calc R U . . .
C20 C -0.1253(3) 0.4292(3) 0.6915(3) 0.0693(9) Uani 1 1 d . . . . .
H20A H -0.187629 0.523719 0.666125 0.083 Uiso 1 1 calc R U . . .
C21 C 0.0355(3) 0.3828(3) 0.6698(3) 0.0599(8) Uani 1 1 d . . . . .
H21A H 0.080376 0.447355 0.631296 0.072 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'
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 C10 111.06(13) . . ?
O3 P1 C16 112.19(10) . . ?
C10 P1 C16 106.18(12) . . ?
O3 P1 C9 111.93(10) . . ?
C10 P1 C9 108.89(11) . . ?
C16 P1 C9 106.30(13) . . ?
C9 O2 H2B 109.5 . . ?
C6 C1 C2 121.0(4) . . ?
C6 C1 H1A 119.5 . . ?
C2 C1 H1A 119.5 . . ?
C3 C2 C1 119.1(4) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 119.3(4) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 C7 123.2(3) . . ?
C1 C6 C7 118.2(3) . . ?
O1 C7 C6 120.9(3) . . ?
O1 C7 C8 121.1(2) . . ?
C6 C7 C8 118.0(3) . . ?
C9 C8 C7 111.9(3) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
O2 C9 C8 113.44(18) . . ?
O2 C9 P1 106.60(15) . . ?
C8 C9 P1 112.5(2) . . ?
O2 C9 H9A 108.1 . . ?
C8 C9 H9A 108.1 . . ?
P1 C9 H9A 108.1 . . ?
C11 C10 C15 117.7(3) . . ?
C11 C10 P1 119.7(2) . . ?
C15 C10 P1 122.5(3) . . ?
C10 C11 C12 121.2(3) . . ?
C10 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
C13 C12 C11 121.2(4) . . ?
C13 C12 H12A 119.4 . . ?
C11 C12 H12A 119.4 . . ?
C14 C13 C12 117.6(4) . . ?
C14 C13 H13A 121.2 . . ?
C12 C13 H13A 121.2 . . ?
C13 C14 C15 123.2(3) . . ?
C13 C14 H14A 118.4 . . ?
C15 C14 H14A 118.4 . . ?
C10 C15 C14 119.0(4) . . ?
C10 C15 H15A 120.5 . . ?
C14 C15 H15A 120.5 . . ?
C17 C16 C21 118.4(2) . . ?
C17 C16 P1 117.8(2) . . ?
C21 C16 P1 123.71(18) . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17A 119.9 . . ?
C18 C17 H17A 119.9 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18A 119.7 . . ?
C17 C18 H18A 119.7 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19A 119.8 . . ?
C20 C19 H19A 119.8 . . ?
C19 C20 C21 119.5(3) . . ?
C19 C20 H20A 120.2 . . ?
C21 C20 H20A 120.2 . . ?
C20 C21 C16 120.8(2) . . ?
C20 C21 H21A 119.6 . . ?
C16 C21 H21A 119.6 . . ?
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 1.4863(16) . ?
P1 C10 1.797(3) . ?
P1 C16 1.799(3) . ?
P1 C9 1.833(3) . ?
O1 C7 1.207(4) . ?
O2 C9 1.413(3) . ?
O2 H2B 0.8200 . ?
C1 C6 1.381(4) . ?
C1 C2 1.382(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.370(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.367(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.386(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.368(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.486(4) . ?
C7 C8 1.523(4) . ?
C8 C9 1.509(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9800 . ?
C10 C11 1.364(5) . ?
C10 C15 1.371(4) . ?
C11 C12 1.387(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.346(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.332(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.392(5) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.383(3) . ?
C16 C21 1.389(4) . ?
C17 C18 1.390(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.357(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.373(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.388(4) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
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
C6 C1 C2 C3 -2.0(5) . . . . ?
C1 C2 C3 C4 4.2(6) . . . . ?
C2 C3 C4 C5 -1.9(5) . . . . ?
C3 C4 C5 C6 -2.8(4) . . . . ?
C4 C5 C6 C1 4.9(4) . . . . ?
C4 C5 C6 C7 -172.8(2) . . . . ?
C2 C1 C6 C5 -2.5(4) . . . . ?
C2 C1 C6 C7 175.3(3) . . . . ?
C5 C6 C7 O1 145.5(3) . . . . ?
C1 C6 C7 O1 -32.2(4) . . . . ?
C5 C6 C7 C8 -32.7(3) . . . . ?
C1 C6 C7 C8 149.6(3) . . . . ?
O1 C7 C8 C9 18.4(4) . . . . ?
C6 C7 C8 C9 -163.4(2) . . . . ?
C7 C8 C9 O2 59.9(3) . . . . ?
C7 C8 C9 P1 -179.08(16) . . . . ?
O3 P1 C9 O2 62.12(19) . . . . ?
C10 P1 C9 O2 -174.71(15) . . . . ?
C16 P1 C9 O2 -60.70(16) . . . . ?
O3 P1 C9 C8 -62.79(19) . . . . ?
C10 P1 C9 C8 60.38(18) . . . . ?
C16 P1 C9 C8 174.39(15) . . . . ?
O3 P1 C10 C11 22.0(3) . . . . ?
C16 P1 C10 C11 144.2(3) . . . . ?
C9 P1 C10 C11 -101.7(3) . . . . ?
O3 P1 C10 C15 -155.6(2) . . . . ?
C16 P1 C10 C15 -33.4(3) . . . . ?
C9 P1 C10 C15 80.7(3) . . . . ?
C15 C10 C11 C12 0.1(5) . . . . ?
P1 C10 C11 C12 -177.7(3) . . . . ?
C10 C11 C12 C13 -0.1(6) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C12 C13 C14 C15 1.0(7) . . . . ?
C11 C10 C15 C14 0.4(5) . . . . ?
P1 C10 C15 C14 178.1(3) . . . . ?
C13 C14 C15 C10 -1.0(7) . . . . ?
O3 P1 C16 C17 24.8(3) . . . . ?
C10 P1 C16 C17 -96.7(2) . . . . ?
C9 P1 C16 C17 147.4(2) . . . . ?
O3 P1 C16 C21 -157.1(2) . . . . ?
C10 P1 C16 C21 81.4(3) . . . . ?
C9 P1 C16 C21 -34.4(3) . . . . ?
C21 C16 C17 C18 -1.2(4) . . . . ?
P1 C16 C17 C18 177.0(2) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
C17 C18 C19 C20 1.8(5) . . . . ?
C18 C19 C20 C21 -2.3(5) . . . . ?
C19 C20 C21 C16 1.2(4) . . . . ?
C17 C16 C21 C20 0.6(4) . . . . ?
P1 C16 C21 C20 -177.5(2) . . . . ?
