#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/06/7050641.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_7050641
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            'C36 H52 O P2'
_chemical_formula_weight         562.72
_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                 103.64(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.235(2)
_cell_length_b                   14.236(3)
_cell_length_c                   21.449(4)
_cell_measurement_temperature    150(2)
_cell_volume                     3333.8(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0829
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            28003
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.000(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         5856
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0751
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0771P)²+2.3882P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1751
_refine_ls_wR_factor_ref         0.1900
_reflns_number_gt                4270
_reflns_number_total             5856
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b306607j.txt
_cod_data_source_block           compound_5b
_cod_original_cell_volume        3333.8(11)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7050641
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 0.84736(8) 0.84618(6) 0.18166(4) 0.0450(3) Uani 1 1 d . . .
P2 P 0.89532(8) 0.73972(6) 0.26112(4) 0.0480(3) Uani 1 1 d . . .
O1 O 0.8261(2) 0.94261(16) 0.20359(11) 0.0567(6) Uani 1 1 d . . .
C1 C 0.7101(3) 0.8002(3) 0.12375(15) 0.0495(8) Uani 1 1 d . . .
C2 C 0.7077(3) 0.7151(3) 0.09750(17) 0.0600(10) Uani 1 1 d . . .
H2 H 0.6336 0.6989 0.0698 0.072 Uiso 1 1 calc R . .
C3 C 0.8049(4) 0.6415(3) 0.10539(19) 0.0643(10) Uani 1 1 d . . .
C4 C 0.8811(4) 0.6389(3) 0.0640(3) 0.0849(13) Uani 1 1 d . . .
H4 H 0.8730 0.6844 0.0322 0.102 Uiso 1 1 calc R . .
C5 C 0.9701(5) 0.5701(4) 0.0686(4) 0.113(2) Uani 1 1 d . . .
H5 H 1.0217 0.5693 0.0404 0.136 Uiso 1 1 calc R . .
C6 C 0.9801(6) 0.5039(5) 0.1151(4) 0.125(2) Uani 1 1 d U . .
H6 H 1.0413 0.4587 0.1195 0.151 Uiso 1 1 calc R . .
C7 C 0.9035(7) 0.5016(4) 0.1555(3) 0.118(2) Uani 1 1 d U . .
H7 H 0.9111 0.4545 0.1863 0.142 Uiso 1 1 calc R . .
C8 C 0.8140(5) 0.5699(3) 0.1505(2) 0.0960(16) Uani 1 1 d . . .
H8 H 0.7600 0.5681 0.1774 0.115 Uiso 1 1 calc R . .
C9 C 0.5987(3) 0.8678(3) 0.10404(17) 0.0583(9) Uani 1 1 d . . .
C10 C 0.6365(4) 0.9543(3) 0.0712(2) 0.0731(12) Uani 1 1 d . . .
H10A H 0.7051 0.9840 0.0994 0.110 Uiso 1 1 calc R . .
H10B H 0.5692 0.9976 0.0609 0.110 Uiso 1 1 calc R . .
H10C H 0.6589 0.9355 0.0325 0.110 Uiso 1 1 calc R . .
C11 C 0.4921(4) 0.8211(4) 0.0558(2) 0.0906(15) Uani 1 1 d . . .
H11A H 0.5198 0.8003 0.0191 0.136 Uiso 1 1 calc R . .
H11B H 0.4268 0.8656 0.0425 0.136 Uiso 1 1 calc R . .
H11C H 0.4629 0.7682 0.0757 0.136 Uiso 1 1 calc R . .
C12 C 0.5519(4) 0.8991(4) 0.1624(2) 0.0819(13) Uani 1 1 d . . .
H12A H 0.5259 0.8452 0.1826 0.123 Uiso 1 1 calc R . .
H12B H 0.4841 0.9413 0.1488 0.123 Uiso 1 1 calc R . .
H12C H 0.6165 0.9306 0.1925 0.123 Uiso 1 1 calc R . .
C13 C 0.9767(3) 0.8455(3) 0.14208(16) 0.0505(8) Uani 1 1 d . . .
H13 H 1.0060 0.7807 0.1416 0.061 Uiso 1 1 calc R . .
C14 C 0.9400(3) 0.8809(3) 0.07231(17) 0.0614(10) Uani 1 1 d . . .
H14A H 0.8741 0.8423 0.0479 0.074 Uiso 1 1 calc R . .
H14B H 0.9105 0.9451 0.0716 0.074 Uiso 1 1 calc R . .
C15 C 1.0486(4) 0.8770(4) 0.0418(2) 0.0802(13) Uani 1 1 d . . .
H15A H 1.0739 0.8121 0.0398 0.096 Uiso 1 1 calc R . .
H15B H 1.0242 0.9007 -0.0018 0.096 Uiso 1 1 calc R . .
C16 C 1.1554(4) 0.9338(4) 0.0787(2) 0.0876(14) Uani 1 1 d . . .
H16A H 1.1337 0.9998 0.0762 0.105 Uiso 1 1 calc R . .
H16B H 1.2248 0.9256 0.0595 0.105 Uiso 1 1 calc R . .
C17 C 1.1908(4) 0.9034(4) 0.1485(2) 0.0798(13) Uani 1 1 d . . .
H17A H 1.2540 0.9450 0.1721 0.096 Uiso 1 1 calc R . .
H17B H 1.2243 0.8404 0.1512 0.096 Uiso 1 1 calc R . .
C18 C 1.0816(3) 0.9052(3) 0.17911(19) 0.0627(10) Uani 1 1 d . . .
H18A H 1.1067 0.8822 0.2228 0.075 Uiso 1 1 calc R . .
H18B H 1.0537 0.9695 0.1807 0.075 Uiso 1 1 calc R . .
C19 C 1.0237(3) 0.8051(3) 0.31500(16) 0.0491(8) Uani 1 1 d . . .
C20 C 0.9989(3) 0.8905(3) 0.33345(15) 0.0518(8) Uani 1 1 d . . .
H20 H 0.9180 0.9088 0.3175 0.062 Uiso 1 1 calc R . .
C21 C 1.0757(3) 0.9626(3) 0.37481(16) 0.0537(9) Uani 1 1 d . . .
C22 C 1.1201(5) 1.0369(3) 0.3467(2) 0.0930(16) Uani 1 1 d . . .
H22 H 1.1046 1.0402 0.3022 0.112 Uiso 1 1 calc R . .
C23 C 1.1872(6) 1.1065(4) 0.3830(3) 0.120(2) Uani 1 1 d . . .
H23 H 1.2175 1.1556 0.3627 0.144 Uiso 1 1 calc R . .
C24 C 1.2097(5) 1.1051(4) 0.4470(3) 0.0992(17) Uani 1 1 d . . .
H24 H 1.2551 1.1529 0.4711 0.119 Uiso 1 1 calc R . .
C25 C 1.1660(5) 1.0335(4) 0.4766(2) 0.0942(16) Uani 1 1 d . . .
H25 H 1.1813 1.0319 0.5211 0.113 Uiso 1 1 calc R . .
C26 C 1.0974(4) 0.9617(3) 0.4401(2) 0.0796(13) Uani 1 1 d . . .
H26 H 1.0665 0.9131 0.4606 0.096 Uiso 1 1 calc R . .
C27 C 1.1444(3) 0.7498(3) 0.33552(18) 0.0590(10) Uani 1 1 d . . .
C28 C 1.1339(5) 0.6846(4) 0.3904(3) 0.119(2) Uani 1 1 d U . .
H28A H 1.1159 0.7209 0.4248 0.178 Uiso 1 1 calc R . .
H28B H 1.2098 0.6517 0.4055 0.178 Uiso 1 1 calc R . .
H28C H 1.0692 0.6401 0.3754 0.178 Uiso 1 1 calc R . .
C29 C 1.2559(4) 0.8126(4) 0.3583(3) 0.1010(18) Uani 1 1 d . . .
H29A H 1.2545 0.8623 0.3279 0.152 Uiso 1 1 calc R . .
H29B H 1.3292 0.7761 0.3621 0.152 Uiso 1 1 calc R . .
H29C H 1.2545 0.8390 0.3994 0.152 Uiso 1 1 calc R . .
C30 C 1.1712(4) 0.6903(3) 0.2811(2) 0.0904(15) Uani 1 1 d . . .
H30A H 1.1069 0.6451 0.2675 0.136 Uiso 1 1 calc R . .
H30B H 1.2478 0.6581 0.2959 0.136 Uiso 1 1 calc R . .
H30C H 1.1758 0.7302 0.2456 0.136 Uiso 1 1 calc R . .
C31 C 0.7628(3) 0.7558(2) 0.29959(16) 0.0505(8) Uani 1 1 d . . .
H31 H 0.7367 0.8217 0.2954 0.061 Uiso 1 1 calc R . .
C32 C 0.8006(3) 0.7295(3) 0.37135(17) 0.0643(10) Uani 1 1 d . . .
H32A H 0.8345 0.6665 0.3757 0.077 Uiso 1 1 calc R . .
H32B H 0.8639 0.7723 0.3934 0.077 Uiso 1 1 calc R . .
C33 C 0.6928(4) 0.7337(3) 0.40252(18) 0.0720(11) Uani 1 1 d . . .
H33A H 0.7188 0.7121 0.4465 0.086 Uiso 1 1 calc R . .
H33B H 0.6663 0.7985 0.4034 0.086 Uiso 1 1 calc R . .
C34 C 0.5864(4) 0.6750(3) 0.36775(19) 0.0690(11) Uani 1 1 d . . .
H34A H 0.6092 0.6091 0.3716 0.083 Uiso 1 1 calc R . .
H34B H 0.5178 0.6838 0.3874 0.083 Uiso 1 1 calc R . .
C35 C 0.5485(3) 0.7011(3) 0.29794(19) 0.0713(11) Uani 1 1 d . . .
H35A H 0.5173 0.7649 0.2939 0.086 Uiso 1 1 calc R . .
H35B H 0.4833 0.6597 0.2762 0.086 Uiso 1 1 calc R . .
C36 C 0.6569(3) 0.6937(3) 0.26622(17) 0.0595(10) Uani 1 1 d . . .
H36A H 0.6842 0.6290 0.2676 0.071 Uiso 1 1 calc R . .
H36B H 0.6305 0.7121 0.2215 0.071 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C13 110.60(15) . . ?
O1 P1 C1 111.52(15) . . ?
C13 P1 C1 108.07(15) . . ?
O1 P1 P2 114.18(10) . . ?
C13 P1 P2 105.71(12) . . ?
C1 P1 P2 106.39(12) . . ?
C19 P2 C31 104.09(15) . . ?
C19 P2 P1 98.35(11) . . ?
C31 P2 P1 100.22(11) . . ?
C2 C1 C9 120.8(3) . . ?
C2 C1 P1 122.3(3) . . ?
C9 C1 P1 116.9(3) . . ?
C1 C2 C3 130.4(3) . . ?
C4 C3 C8 118.5(4) . . ?
C4 C3 C2 119.8(4) . . ?
C8 C3 C2 121.5(4) . . ?
C3 C4 C5 121.5(5) . . ?
C6 C5 C4 118.4(6) . . ?
C7 C6 C5 122.1(6) . . ?
C6 C7 C8 119.4(6) . . ?
C7 C8 C3 120.0(5) . . ?
C10 C9 C12 109.2(4) . . ?
C10 C9 C11 107.1(3) . . ?
C12 C9 C11 108.2(3) . . ?
C10 C9 C1 109.3(3) . . ?
C12 C9 C1 111.5(3) . . ?
C11 C9 C1 111.4(3) . . ?
C18 C13 C14 108.8(3) . . ?
C18 C13 P1 110.8(2) . . ?
C14 C13 P1 112.6(2) . . ?
C15 C14 C13 110.4(3) . . ?
C16 C15 C14 112.1(4) . . ?
C15 C16 C17 110.9(4) . . ?
C16 C17 C18 111.7(3) . . ?
C13 C18 C17 111.7(3) . . ?
C20 C19 C27 128.0(3) . . ?
C20 C19 P2 117.0(3) . . ?
C27 C19 P2 115.0(3) . . ?
C19 C20 C21 132.4(3) . . ?
C26 C21 C22 117.6(4) . . ?
C26 C21 C20 122.9(4) . . ?
C22 C21 C20 119.3(3) . . ?
C21 C22 C23 121.2(5) . . ?
C24 C23 C22 121.2(5) . . ?
C23 C24 C25 119.4(5) . . ?
C24 C25 C26 120.0(5) . . ?
C21 C26 C25 120.5(5) . . ?
C29 C27 C28 108.5(4) . . ?
C29 C27 C30 106.0(4) . . ?
C28 C27 C30 108.5(4) . . ?
C29 C27 C19 113.2(3) . . ?
C28 C27 C19 108.0(3) . . ?
C30 C27 C19 112.6(3) . . ?
C36 C31 C32 109.2(3) . . ?
C36 C31 P2 109.6(2) . . ?
C32 C31 P2 110.4(2) . . ?
C33 C32 C31 111.7(3) . . ?
C34 C33 C32 112.5(3) . . ?
C35 C34 C33 111.2(3) . . ?
C34 C35 C36 110.9(3) . . ?
C31 C36 C35 111.5(3) . . ?
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 1.489(2) . ?
P1 C13 1.848(3) . ?
P1 C1 1.856(3) . ?
P1 P2 2.2493(13) . ?
P2 C19 1.870(3) . ?
P2 C31 1.878(3) . ?
C1 C2 1.334(5) . ?
C1 C9 1.556(5) . ?
C2 C3 1.494(5) . ?
C3 C4 1.371(6) . ?
C3 C8 1.392(6) . ?
C4 C5 1.387(7) . ?
C5 C6 1.359(9) . ?
C6 C7 1.358(9) . ?
C7 C8 1.385(8) . ?
C9 C10 1.529(5) . ?
C9 C12 1.534(5) . ?
C9 C11 1.537(5) . ?
C13 C18 1.517(5) . ?
C13 C14 1.540(5) . ?
C14 C15 1.516(5) . ?
C15 C16 1.506(7) . ?
C16 C17 1.519(6) . ?
C17 C18 1.522(5) . ?
C19 C20 1.329(5) . ?
C19 C27 1.539(5) . ?
C20 C21 1.492(5) . ?
C21 C26 1.364(5) . ?
C21 C22 1.368(6) . ?
C22 C23 1.371(7) . ?
C23 C24 1.337(7) . ?
C24 C25 1.352(7) . ?
C25 C26 1.402(7) . ?
C27 C29 1.523(6) . ?
C27 C28 1.526(6) . ?
C27 C30 1.530(6) . ?
C31 C36 1.520(5) . ?
C31 C32 1.543(5) . ?
C32 C33 1.517(5) . ?
C33 C34 1.505(6) . ?
C34 C35 1.504(5) . ?
C35 C36 1.532(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139175201
