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#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/38/1513861.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_1513861
loop_
_publ_author_name
'Kortmann, Felix A.'
'Chang, Mu-Chieh'
'Otten, Edwin'
'Couzijn, Erik P. A.'
'Lutz, Martin'
'Minnaard, Adriaan J.'
_publ_section_title
;
 Consecutive dynamic resolutions of phosphine oxides
;
_journal_issue                   4
_journal_name_full               'Chemical Science'
_journal_page_first              1322
_journal_paper_doi               10.1039/c3sc52913d
_journal_volume                  5
_journal_year                    2014
_chemical_formula_sum            'C17 H21 O2 P'
_chemical_formula_weight         288.31
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 116.360(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.4308(14)
_cell_length_b                   6.0890(4)
_cell_length_c                   13.0171(8)
_cell_measurement_reflns_used    7613
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      54.104
_cell_measurement_theta_min      6.363
_cell_volume                     1522.01(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15838
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_correction_T_min  0.9349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3320
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0352P)²+0.7414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0764
_reflns_number_gt                2992
_reflns_number_total             3320
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc52913d.txt
_cod_data_source_block           mo_molan083_0m
_cod_original_sg_symbol_H-M      C2
_cod_database_code               1513861
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
P1 P 0.66365(2) 0.78981(7) 0.27051(4) 0.01543(11) Uani 1 1 d .
O1 O 0.68328(6) 0.5520(2) 0.29481(11) 0.0193(3) Uani 1 1 d .
O2 O 0.73670(7) 0.8915(2) 0.48374(11) 0.0191(3) Uani 1 1 d .
H2 H 0.7654 0.9700 0.5367 0.029 Uiso 1 1 calc R
C1 C 0.73037(9) 0.9689(3) 0.37601(15) 0.0165(4) Uani 1 1 d .
H1 H 0.7137 1.1244 0.3639 0.020 Uiso 1 1 calc R
C2 C 0.79830(9) 0.9520(3) 0.36629(15) 0.0167(4) Uani 1 1 d .
C3 C 0.82137(10) 1.1275(3) 0.32314(16) 0.0210(4) Uani 1 1 d .
H3 H 0.7941 1.2571 0.2979 0.025 Uiso 1 1 calc R
C4 C 0.88431(10) 1.1122(3) 0.31718(17) 0.0244(4) Uani 1 1 d .
H4 H 0.9001 1.2324 0.2885 0.029 Uiso 1 1 calc R
C5 C 0.92419(10) 0.9235(4) 0.35271(18) 0.0258(5) Uani 1 1 d .
H5 H 0.9671 0.9139 0.3481 0.031 Uiso 1 1 calc R
C6 C 0.90125(10) 0.7483(3) 0.39512(17) 0.0253(5) Uani 1 1 d .
H6 H 0.9284 0.6182 0.4195 0.030 Uiso 1 1 calc R
C7 C 0.83856(9) 0.7634(4) 0.40188(16) 0.0213(4) Uani 1 1 d .
H7 H 0.8231 0.6434 0.4312 0.026 Uiso 1 1 calc R
C8 C 0.66052(9) 0.8756(3) 0.13508(16) 0.0177(4) Uani 1 1 d .
C9 C 0.67822(9) 0.7215(3) 0.07459(16) 0.0216(4) Uani 1 1 d .
H9 H 0.6901 0.5766 0.1039 0.026 Uiso 1 1 calc R
C10 C 0.67882(9) 0.7761(4) -0.02884(15) 0.0244(4) Uani 1 1 d .
H10 H 0.6914 0.6693 -0.0695 0.029 Uiso 1 1 calc R
C11 C 0.66095(10) 0.9871(3) -0.07220(17) 0.0247(5) Uani 1 1 d .
H11 H 0.6603 1.0241 -0.1436 0.030 Uiso 1 1 calc R
C12 C 0.64402(11) 1.1441(3) -0.01159(17) 0.0263(5) Uani 1 1 d .
H12 H 0.6320 1.2887 -0.0413 0.032 Uiso 1 1 calc R
C13 C 0.64453(10) 1.0904(3) 0.09252(17) 0.0226(4) Uani 1 1 d .
H13 H 0.6341 1.1992 0.1349 0.027 Uiso 1 1 calc R
C14 C 0.57840(9) 0.8426(3) 0.26885(16) 0.0195(4) Uani 1 1 d .
C15 C 0.52405(10) 0.7158(4) 0.16645(18) 0.0314(5) Uani 1 1 d .
H15A H 0.5372 0.5605 0.1727 0.047 Uiso 1 1 calc R
H15B H 0.5218 0.7764 0.0951 0.047 Uiso 1 1 calc R
H15C H 0.4784 0.7296 0.1660 0.047 Uiso 1 1 calc R
C16 C 0.55919(12) 1.0850(4) 0.2594(2) 0.0335(5) Uani 1 1 d .
H16A H 0.5160 1.1029 0.2670 0.050 Uiso 1 1 calc R
H16B H 0.5526 1.1412 0.1847 0.050 Uiso 1 1 calc R
H16C H 0.5967 1.1670 0.3206 0.050 Uiso 1 1 calc R
C17 C 0.58071(9) 0.7492(4) 0.38001(17) 0.0251(5) Uani 1 1 d .
H17A H 0.6160 0.8279 0.4459 0.038 Uiso 1 1 calc R
H17B H 0.5926 0.5928 0.3860 0.038 Uiso 1 1 calc R
H17C H 0.5350 0.7673 0.3791 0.038 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'
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
O1 P1 C8 111.65(8)
O1 P1 C1 111.25(8)
C8 P1 C1 103.69(8)
O1 P1 C14 110.71(8)
C8 P1 C14 109.25(8)
C1 P1 C14 110.07(8)
O2 C1 C2 112.51(14)
O2 C1 P1 103.97(12)
C2 C1 P1 110.74(12)
C7 C2 C3 119.29(17)
C7 C2 C1 120.32(16)
C3 C2 C1 120.38(17)
C4 C3 C2 119.87(18)
C5 C4 C3 120.55(18)
C4 C5 C6 119.75(18)
C5 C6 C7 119.87(19)
C2 C7 C6 120.67(19)
C9 C8 C13 119.27(18)
C9 C8 P1 117.25(14)
C13 C8 P1 123.40(15)
C8 C9 C10 120.77(19)
C11 C10 C9 119.68(19)
C12 C11 C10 120.13(18)
C11 C12 C13 120.13(19)
C12 C13 C8 119.98(19)
C16 C14 C15 110.13(17)
C16 C14 C17 109.21(17)
C15 C14 C17 109.10(16)
C16 C14 P1 113.61(13)
C15 C14 P1 106.77(13)
C17 C14 P1 107.89(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.5016(13)
P1 C8 1.8111(19)
P1 C1 1.8372(18)
P1 C14 1.8456(18)
O2 C1 1.427(2)
C1 C2 1.520(2)
C2 C7 1.387(3)
C2 C3 1.396(3)
C3 C4 1.388(3)
C4 C5 1.383(3)
C5 C6 1.388(3)
C6 C7 1.388(3)
C8 C9 1.382(3)
C8 C13 1.402(3)
C9 C10 1.392(3)
C10 C11 1.387(3)
C11 C12 1.387(3)
C12 C13 1.389(3)
C14 C16 1.523(3)
C14 C15 1.533(3)
C14 C17 1.535(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139042086
