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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/7/05/06/7050643.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_7050643
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 H27 O P'
_chemical_formula_weight         290.37
_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                 95.05(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3490(13)
_cell_length_b                   14.028(3)
_cell_length_c                   19.120(4)
_cell_measurement_temperature    150(2)
_cell_volume                     1696.3(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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0975
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29071
_diffrn_reflns_theta_full        25.94
_diffrn_reflns_theta_max         25.94
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0119(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0408
_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)+(0.0441P)²+0.6276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                2636
_reflns_number_total             3294
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b306607j.txt
_cod_data_source_block           compound_6
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7050643
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
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.51968(7) 0.73991(3) 0.28184(2) 0.02474(15) Uani 1 1 d . . .
O1 O 0.32274(18) 0.79719(9) 0.28194(6) 0.0350(3) Uani 1 1 d . . .
C1 C 0.7565(3) 0.79786(11) 0.32215(8) 0.0225(4) Uani 1 1 d . . .
C2 C 0.8601(3) 0.86212(12) 0.28637(8) 0.0249(4) Uani 1 1 d . . .
H2 H 0.9799 0.8887 0.3103 0.030 Uiso 1 1 calc R . .
C3 C 0.8085(3) 0.89633(11) 0.21361(8) 0.0242(4) Uani 1 1 d . . .
C4 C 0.6105(3) 0.93226(12) 0.18968(9) 0.0302(4) Uani 1 1 d . . .
H4 H 0.5053 0.9373 0.2204 0.036 Uiso 1 1 calc R . .
C5 C 0.5693(3) 0.96061(12) 0.12017(10) 0.0356(5) Uani 1 1 d . . .
H5 H 0.4367 0.9845 0.1046 0.043 Uiso 1 1 calc R . .
C6 C 0.7237(3) 0.95354(13) 0.07422(10) 0.0379(5) Uani 1 1 d . . .
H6 H 0.6947 0.9716 0.0276 0.046 Uiso 1 1 calc R . .
C7 C 0.9219(3) 0.91956(14) 0.09757(10) 0.0375(5) Uani 1 1 d . . .
H7 H 1.0265 0.9151 0.0666 0.045 Uiso 1 1 calc R . .
C8 C 0.9652(3) 0.89218(12) 0.16705(9) 0.0298(4) Uani 1 1 d . . .
H8 H 1.0999 0.8709 0.1827 0.036 Uiso 1 1 calc R . .
C9 C 0.8352(3) 0.76595(12) 0.39705(9) 0.0264(4) Uani 1 1 d . . .
C10 C 0.9341(3) 0.66633(13) 0.39369(9) 0.0337(4) Uani 1 1 d . . .
H10A H 0.9863 0.6466 0.4401 0.051 Uiso 1 1 calc R . .
H10B H 1.0488 0.6682 0.3642 0.051 Uiso 1 1 calc R . .
H10C H 0.8291 0.6219 0.3747 0.051 Uiso 1 1 calc R . .
C11 C 0.6513(3) 0.76441(14) 0.44409(9) 0.0347(4) Uani 1 1 d . . .
H11A H 0.5456 0.7202 0.4253 0.052 Uiso 1 1 calc R . .
H11B H 0.5906 0.8270 0.4457 0.052 Uiso 1 1 calc R . .
H11C H 0.7027 0.7451 0.4907 0.052 Uiso 1 1 calc R . .
C12 C 1.0054(3) 0.83319(13) 0.43088(9) 0.0353(4) Uani 1 1 d . . .
H12A H 1.0474 0.8122 0.4778 0.053 Uiso 1 1 calc R . .
H12B H 0.9496 0.8967 0.4321 0.053 Uiso 1 1 calc R . .
H12C H 1.1258 0.8327 0.4038 0.053 Uiso 1 1 calc R . .
C13 C 0.5719(2) 0.69074(12) 0.19726(8) 0.0237(4) Uani 1 1 d . . .
H13 H 0.5937 0.7438 0.1654 0.028 Uiso 1 1 calc R . .
C14 C 0.7710(3) 0.62843(12) 0.20236(9) 0.0272(4) Uani 1 1 d . . .
H14A H 0.8928 0.6667 0.2187 0.033 Uiso 1 1 calc R . .
H14B H 0.7565 0.5777 0.2361 0.033 Uiso 1 1 calc R . .
C15 C 0.8051(3) 0.58538(13) 0.13091(9) 0.0300(4) Uani 1 1 d . . .
H15A H 0.8329 0.6361 0.0984 0.036 Uiso 1 1 calc R . .
H15B H 0.9278 0.5439 0.1356 0.036 Uiso 1 1 calc R . .
C16 C 0.6133(3) 0.52868(13) 0.10145(10) 0.0335(4) Uani 1 1 d . . .
H16A H 0.5939 0.4742 0.1315 0.040 Uiso 1 1 calc R . .
H16B H 0.6374 0.5050 0.0552 0.040 Uiso 1 1 calc R . .
C17 C 0.4141(3) 0.58983(13) 0.09644(9) 0.0322(4) Uani 1 1 d . . .
H17A H 0.2934 0.5508 0.0803 0.039 Uiso 1 1 calc R . .
H17B H 0.4273 0.6400 0.0622 0.039 Uiso 1 1 calc R . .
C18 C 0.3763(3) 0.63439(13) 0.16723(9) 0.0280(4) Uani 1 1 d . . .
H18A H 0.3450 0.5846 0.1999 0.034 Uiso 1 1 calc R . .
H18B H 0.2552 0.6767 0.1614 0.034 Uiso 1 1 calc R . .
H1 H 0.510(3) 0.6587(12) 0.3202(9) 0.026(4) 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 115.22(8) . . ?
O1 P1 C1 114.94(8) . . ?
C13 P1 C1 109.77(8) . . ?
C2 C1 C9 122.44(15) . . ?
C2 C1 P1 120.61(12) . . ?
C9 C1 P1 116.89(12) . . ?
C1 C2 C3 128.32(15) . . ?
C4 C3 C8 118.66(15) . . ?
C4 C3 C2 122.98(16) . . ?
C8 C3 C2 118.36(15) . . ?
C5 C4 C3 120.39(17) . . ?
C6 C5 C4 120.34(18) . . ?
C5 C6 C7 119.87(17) . . ?
C6 C7 C8 120.18(18) . . ?
C7 C8 C3 120.52(17) . . ?
C12 C9 C10 107.57(14) . . ?
C12 C9 C11 107.79(15) . . ?
C10 C9 C11 110.27(15) . . ?
C12 C9 C1 111.85(14) . . ?
C10 C9 C1 109.01(13) . . ?
C11 C9 C1 110.31(14) . . ?
C14 C13 C18 111.37(14) . . ?
C14 C13 P1 111.97(11) . . ?
C18 C13 P1 108.83(11) . . ?
C15 C14 C13 110.49(14) . . ?
C16 C15 C14 111.48(15) . . ?
C15 C16 C17 111.22(15) . . ?
C16 C17 C18 111.64(14) . . ?
C17 C18 C13 110.82(14) . . ?
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 1.4865(13) . ?
P1 C13 1.8153(17) . ?
P1 C1 1.8197(17) . ?
C1 C2 1.339(2) . ?
C1 C9 1.541(2) . ?
C2 C3 1.481(2) . ?
C3 C4 1.394(2) . ?
C3 C8 1.394(3) . ?
C4 C5 1.390(2) . ?
C5 C6 1.376(3) . ?
C6 C7 1.383(3) . ?
C7 C8 1.387(2) . ?
C9 C12 1.534(2) . ?
C9 C10 1.536(2) . ?
C9 C11 1.536(3) . ?
C13 C14 1.533(2) . ?
C13 C18 1.540(2) . ?
C14 C15 1.526(2) . ?
C15 C16 1.521(2) . ?
C16 C17 1.524(2) . ?
C17 C18 1.529(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139175203
