#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/30/7123073.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_7123073
loop_
_publ_author_name
'Krempner, Clemens'
'Brar, Amandeep'
'Unruh, Daniel K.'
'Aquino, Adelia'
_publ_section_title
;
 Lewis Acid Base Chemistry of Bestmann’s Ylide, Ph3PCCO, and its
 Bulkier Analogue, (Cyclohexyl)3PCCO
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01239G
_journal_year                    2019
_chemical_formula_sum            'C20 H15 O P'
_chemical_formula_weight         302.29
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-11-08T13:16:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-11-28 deposited with the CCDC.    2019-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.534(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.703(10)
_cell_length_b                   10.124(9)
_cell_length_c                   14.561(13)
_cell_measurement_reflns_used    8993
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.30
_cell_volume                     1575(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω 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  0.0303
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21843
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.139
_diffrn_reflns_theta_min         2.295
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       blade
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.465
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0311P)²+0.7433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0857
_reflns_Friedel_coverage         0
_reflns_number_gt                2868
_reflns_number_total             3466
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc01239g2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7123073
_shelx_estimated_absorpt_t_min   0.924
_shelx_estimated_absorpt_t_max   0.982
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
P1 P 0.40222(3) 0.78110(4) 0.76129(2) 0.02007(10) Uani 1 1 d . .
O1 O 0.55651(11) 1.09675(12) 0.87783(8) 0.0407(3) Uani 1 1 d . .
C1 C 0.49957(14) 0.90880(16) 0.77909(10) 0.0293(3) Uani 1 1 d . .
C2 C 0.52450(13) 1.00381(15) 0.83153(10) 0.0240(3) Uani 1 1 d . .
C3 C 0.33963(12) 0.77955(14) 0.64308(9) 0.0211(3) Uani 1 1 d . .
C4 C 0.34820(13) 0.89429(15) 0.59063(10) 0.0259(3) Uani 1 1 d . .
H4 H 0.388852 0.970225 0.616555 0.031 Uiso 1 1 calc R U
C5 C 0.29701(14) 0.89746(16) 0.50002(10) 0.0310(4) Uani 1 1 d . .
H5 H 0.303246 0.975321 0.464174 0.037 Uiso 1 1 calc R U
C6 C 0.23702(14) 0.78657(17) 0.46249(10) 0.0309(4) Uani 1 1 d . .
H6 H 0.201216 0.789279 0.401177 0.037 Uiso 1 1 calc R U
C7 C 0.22901(14) 0.67181(17) 0.51393(10) 0.0297(3) Uani 1 1 d . .
H7 H 0.187963 0.596303 0.4877 0.036 Uiso 1 1 calc R U
C8 C 0.28122(13) 0.66711(15) 0.60424(10) 0.0254(3) Uani 1 1 d . .
H8 H 0.277113 0.588092 0.639116 0.031 Uiso 1 1 calc R U
C9 C 0.27246(13) 0.78258(14) 0.83543(9) 0.0202(3) Uani 1 1 d . .
C10 C 0.29822(14) 0.81685(15) 0.92798(9) 0.0249(3) Uani 1 1 d . .
H10 H 0.381397 0.8376 0.949762 0.03 Uiso 1 1 calc R U
C11 C 0.20197(14) 0.82046(16) 0.98784(10) 0.0290(3) Uani 1 1 d . .
H11 H 0.219404 0.844064 1.05046 0.035 Uiso 1 1 calc R U
C12 C 0.07994(14) 0.78950(15) 0.95614(10) 0.0282(3) Uani 1 1 d . .
H12 H 0.014218 0.792485 0.997063 0.034 Uiso 1 1 calc R U
C13 C 0.05446(14) 0.75431(15) 0.86477(10) 0.0281(3) Uani 1 1 d . .
H13 H -0.028667 0.732442 0.843504 0.034 Uiso 1 1 calc R U
C14 C 0.14999(13) 0.75086(14) 0.80410(10) 0.0244(3) Uani 1 1 d . .
H14 H 0.132029 0.727011 0.741578 0.029 Uiso 1 1 calc R U
C15 C 0.48408(12) 0.62624(14) 0.78159(9) 0.0217(3) Uani 1 1 d . .
C16 C 0.45232(13) 0.53704(15) 0.84947(10) 0.0255(3) Uani 1 1 d . .
H16 H 0.38121 0.553024 0.883812 0.031 Uiso 1 1 calc R U
C17 C 0.52508(15) 0.42446(16) 0.86681(11) 0.0309(3) Uani 1 1 d . .
H17 H 0.503429 0.363644 0.912906 0.037 Uiso 1 1 calc R U
C18 C 0.62887(15) 0.40129(17) 0.81688(11) 0.0341(4) Uani 1 1 d . .
H18 H 0.67852 0.324775 0.829117 0.041 Uiso 1 1 calc R U
C19 C 0.66077(15) 0.48931(17) 0.74900(11) 0.0346(4) Uani 1 1 d . .
H19 H 0.731888 0.472667 0.714804 0.042 Uiso 1 1 calc R U
C20 C 0.58903(14) 0.60133(16) 0.73110(10) 0.0289(3) Uani 1 1 d . .
H20 H 0.610939 0.661352 0.684586 0.035 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C1 P1 C3 110.20(7)
C1 P1 C9 113.26(8)
C3 P1 C9 108.35(9)
C1 P1 C15 110.71(10)
C3 P1 C15 107.15(7)
C9 P1 C15 106.91(7)
C2 C1 P1 143.13(13)
O1 C2 C1 174.78(16)
C4 C3 C8 119.86(14)
C4 C3 P1 118.72(11)
C8 C3 P1 121.41(11)
C3 C4 C5 120.02(14)
C3 C4 H4 120
C5 C4 H4 120
C6 C5 C4 119.86(15)
C6 C5 H5 120.1
C4 C5 H5 120.1
C7 C6 C5 120.46(15)
C7 C6 H6 119.8
C5 C6 H6 119.8
C6 C7 C8 120.12(15)
C6 C7 H7 119.9
C8 C7 H7 119.9
C7 C8 C3 119.65(14)
C7 C8 H8 120.2
C3 C8 H8 120.2
C14 C9 C10 119.68(13)
C14 C9 P1 122.78(12)
C10 C9 P1 117.54(11)
C11 C10 C9 119.97(14)
C11 C10 H10 120
C9 C10 H10 120
C10 C11 C12 120.13(15)
C10 C11 H11 119.9
C12 C11 H11 119.9
C13 C12 C11 119.99(13)
C13 C12 H12 120
C11 C12 H12 120
C12 C13 C14 120.40(14)
C12 C13 H13 119.8
C14 C13 H13 119.8
C13 C14 C9 119.83(14)
C13 C14 H14 120.1
C9 C14 H14 120.1
C16 C15 C20 119.51(14)
C16 C15 P1 122.61(11)
C20 C15 P1 117.71(12)
C17 C16 C15 119.94(14)
C17 C16 H16 120
C15 C16 H16 120
C18 C17 C16 120.03(15)
C18 C17 H17 120
C16 C17 H17 120
C17 C18 C19 120.35(15)
C17 C18 H18 119.8
C19 C18 H18 119.8
C20 C19 C18 120.09(15)
C20 C19 H19 120
C18 C19 H19 120
C19 C20 C15 120.07(15)
C19 C20 H20 120
C15 C20 H20 120
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C1 1.6707(19)
P1 C3 1.808(2)
P1 C9 1.8110(18)
P1 C15 1.811(2)
O1 C2 1.1953(19)
C1 C2 1.247(2)
C3 C4 1.396(2)
C3 C8 1.401(2)
C4 C5 1.398(2)
C4 H4 0.95
C5 C6 1.388(2)
C5 H5 0.95
C6 C7 1.388(2)
C6 H6 0.95
C7 C8 1.398(2)
C7 H7 0.95
C8 H8 0.95
C9 C14 1.398(2)
C9 C10 1.402(2)
C10 C11 1.390(2)
C10 H10 0.95
C11 C12 1.394(2)
C11 H11 0.95
C12 C13 1.388(2)
C12 H12 0.95
C13 C14 1.392(2)
C13 H13 0.95
C14 H14 0.95
C15 C16 1.396(2)
C15 C20 1.403(2)
C16 C17 1.395(2)
C16 H16 0.95
C17 C18 1.385(2)
C17 H17 0.95
C18 C19 1.389(3)
C18 H18 0.95
C19 C20 1.385(2)
C19 H19 0.95
C20 H20 0.95
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 359581
