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#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/06/7050644.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_7050644
loop_
_publ_author_name
'Brym, Markus'
'Jones, Cameron'
'Waugh, Mark'
'Hey-Hawkins, Evamarie'
'Majoumo, Felecite'
_publ_section_title
;
 Reactions of phosphavinyl Grignard reagents with aldehydes: synthesis,
 characterisation and further reactivity of ?-phosphaallylic alcohols
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1614
_journal_paper_doi               10.1039/b306607j
_journal_volume                  27
_journal_year                    2003
_chemical_formula_sum            'C18 H29 O2 P'
_chemical_formula_weight         308.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.12(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0830(12)
_cell_length_b                   19.234(4)
_cell_length_c                   14.925(3)
_cell_measurement_temperature    150(2)
_cell_volume                     1719.1(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_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  0.1020
_diffrn_reflns_av_sigmaI/netI    0.0701
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16590
_diffrn_reflns_theta_full        24.92
_diffrn_reflns_theta_max         24.92
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0556
_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)+(0.0285P)²+1.6792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                2257
_reflns_number_total             2988
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b306607j.txt
_cod_data_source_block           compound_2
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7050644
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.25614(11) 0.71502(4) 0.83116(5) 0.0233(2) Uani 1 1 d . . .
O1 O 0.4453(3) 0.70372(10) 0.78054(13) 0.0321(5) Uani 1 1 d . . .
O2 O 0.1564(4) 0.64649(11) 0.63561(14) 0.0385(5) Uani 1 1 d . . .
C1 C 0.0007(4) 0.67145(14) 0.77525(17) 0.0223(6) Uani 1 1 d . . .
H1 H -0.1261 0.6980 0.7932 0.027 Uiso 1 1 calc R . .
C2 C -0.0214(5) 0.68074(15) 0.67031(19) 0.0301(7) Uani 1 1 d . . .
H2 H -0.1634 0.6573 0.6419 0.036 Uiso 1 1 calc R . .
C3 C -0.0444(4) 0.75702(14) 0.64319(17) 0.0249(6) Uani 1 1 d . . .
C4 C -0.2318(4) 0.79442(15) 0.65864(18) 0.0277(6) Uani 1 1 d . . .
H4 H -0.3469 0.7713 0.6825 0.033 Uiso 1 1 calc R . .
C5 C -0.2507(5) 0.86424(16) 0.6397(2) 0.0337(7) Uani 1 1 d . . .
H5 H -0.3782 0.8890 0.6509 0.040 Uiso 1 1 calc R . .
C6 C -0.0857(5) 0.89881(16) 0.6044(2) 0.0351(7) Uani 1 1 d . . .
H6 H -0.0978 0.9473 0.5926 0.042 Uiso 1 1 calc R . .
C7 C 0.0960(5) 0.86239(16) 0.58636(19) 0.0333(7) Uani 1 1 d . . .
H7 H 0.2082 0.8857 0.5609 0.040 Uiso 1 1 calc R . .
C8 C 0.1171(5) 0.79159(15) 0.60515(17) 0.0297(7) Uani 1 1 d . . .
H8 H 0.2425 0.7668 0.5919 0.036 Uiso 1 1 calc R . .
C9 C -0.0227(4) 0.59484(14) 0.80860(18) 0.0261(6) Uani 1 1 d . . .
C10 C -0.2043(5) 0.55589(15) 0.7430(2) 0.0337(7) Uani 1 1 d . . .
H10A H -0.2361 0.5115 0.7702 0.051 Uiso 1 1 calc R . .
H10B H -0.1521 0.5473 0.6855 0.051 Uiso 1 1 calc R . .
H10C H -0.3405 0.5841 0.7314 0.051 Uiso 1 1 calc R . .
C11 C -0.0986(5) 0.59847(16) 0.90149(19) 0.0328(7) Uani 1 1 d . . .
H11A H -0.2443 0.6215 0.8945 0.049 Uiso 1 1 calc R . .
H11B H 0.0110 0.6249 0.9442 0.049 Uiso 1 1 calc R . .
H11C H -0.1108 0.5513 0.9249 0.049 Uiso 1 1 calc R . .
C12 C 0.1948(5) 0.55321(15) 0.8181(2) 0.0348(7) Uani 1 1 d . . .
H12A H 0.1680 0.5054 0.8360 0.052 Uiso 1 1 calc R . .
H12B H 0.3081 0.5747 0.8647 0.052 Uiso 1 1 calc R . .
H12C H 0.2477 0.5529 0.7598 0.052 Uiso 1 1 calc R . .
C13 C 0.1969(4) 0.80557(14) 0.85123(18) 0.0243(6) Uani 1 1 d . . .
H13 H 0.1174 0.8256 0.7926 0.029 Uiso 1 1 calc R . .
C14 C 0.4135(5) 0.84645(15) 0.8798(2) 0.0308(7) Uani 1 1 d . . .
H14A H 0.4956 0.8280 0.9381 0.037 Uiso 1 1 calc R . .
H14B H 0.5097 0.8411 0.8332 0.037 Uiso 1 1 calc R . .
C15 C 0.3600(5) 0.92312(15) 0.8905(2) 0.0349(7) Uani 1 1 d . . .
H15A H 0.5004 0.9491 0.9107 0.042 Uiso 1 1 calc R . .
H15B H 0.2879 0.9421 0.8309 0.042 Uiso 1 1 calc R . .
C16 C 0.2060(5) 0.93339(16) 0.9593(2) 0.0351(7) Uani 1 1 d . . .
H16A H 0.1660 0.9832 0.9614 0.042 Uiso 1 1 calc R . .
H16B H 0.2854 0.9199 1.0205 0.042 Uiso 1 1 calc R . .
C17 C -0.0068(5) 0.89015(16) 0.9351(2) 0.0394(8) Uani 1 1 d . . .
H17A H -0.0960 0.8946 0.9843 0.047 Uiso 1 1 calc R . .
H17B H -0.0975 0.9085 0.8785 0.047 Uiso 1 1 calc R . .
C18 C 0.0443(5) 0.81360(15) 0.9220(2) 0.0328(7) Uani 1 1 d . . .
H18A H -0.0968 0.7880 0.9015 0.039 Uiso 1 1 calc R . .
H18B H 0.1180 0.7934 0.9807 0.039 Uiso 1 1 calc R . .
H19 H 0.306(8) 0.660(3) 0.682(3) 0.111(17) Uiso 1 1 d . . .
H20 H 0.301(4) 0.6889(14) 0.9174(18) 0.027(7) Uiso 1 1 d . . .
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
O1 P1 C13 114.49(12) . . ?
O1 P1 C1 111.63(12) . . ?
C13 P1 C1 109.70(12) . . ?
O1 P1 H20 112.2(11) . . ?
C13 P1 H20 102.2(11) . . ?
C1 P1 H20 106.0(11) . . ?
C2 O2 H19 105(3) . . ?
C2 C1 C9 115.4(2) . . ?
C2 C1 P1 108.77(18) . . ?
C9 C1 P1 113.69(18) . . ?
C2 C1 H1 106.1 . . ?
C9 C1 H1 106.1 . . ?
P1 C1 H1 106.1 . . ?
O2 C2 C3 112.7(2) . . ?
O2 C2 C1 111.8(2) . . ?
C3 C2 C1 111.4(2) . . ?
O2 C2 H2 106.8 . . ?
C3 C2 H2 106.8 . . ?
C1 C2 H2 106.8 . . ?
C8 C3 C4 118.4(3) . . ?
C8 C3 C2 122.2(3) . . ?
C4 C3 C2 119.4(2) . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 120.5(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 120.3(3) . . ?
C3 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C12 C9 C10 108.5(2) . . ?
C12 C9 C11 109.4(2) . . ?
C10 C9 C11 107.5(2) . . ?
C12 C9 C1 113.3(2) . . ?
C10 C9 C1 110.5(2) . . ?
C11 C9 C1 107.5(2) . . ?
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 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 110.7(2) . . ?
C14 C13 P1 110.69(18) . . ?
C18 C13 P1 111.88(19) . . ?
C14 C13 H13 107.8 . . ?
C18 C13 H13 107.8 . . ?
P1 C13 H13 107.8 . . ?
C15 C14 C13 109.7(2) . . ?
C15 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C16 C15 C14 111.4(2) . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C17 111.5(2) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C18 C17 C16 111.9(2) . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 C13 110.4(2) . . ?
C17 C18 H18A 109.6 . . ?
C13 C18 H18A 109.6 . . ?
C17 C18 H18B 109.6 . . ?
C13 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
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 1.4992(19) . ?
P1 C13 1.814(3) . ?
P1 C1 1.832(3) . ?
P1 H20 1.36(3) . ?
O2 C2 1.438(3) . ?
O2 H19 1.07(5) . ?
C1 C2 1.559(4) . ?
C1 C9 1.570(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.522(4) . ?
C2 H2 1.0000 . ?
C3 C8 1.387(4) . ?
C3 C4 1.401(4) . ?
C4 C5 1.373(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.375(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C12 1.532(4) . ?
C9 C10 1.536(4) . ?
C9 C11 1.538(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.529(4) . ?
C13 C18 1.532(4) . ?
C13 H13 1.0000 . ?
C14 C15 1.525(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.519(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.528(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.525(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139175204
