#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:20:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178466 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/87/4028772.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_4028772
loop_
_publ_author_name
'Elena D. Matveeva'
'Tatyana A. Podrugina'
'Marina A. Taranova'
'Dmitriy S. Vinogradov'
'Rolf Gleiter'
'Nikolay S. Zefirov'
_publ_section_title
;
 Phosphonium-Iodonium Ylides with Heteroatomic Groups in the Synthesis of
 Annelated P-Containing Heterocycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11691
_journal_page_last               11697
_journal_paper_doi               10.1021/jo401514d
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C31 H30 O3 P2'
_chemical_formula_weight         512.49
_chemical_name_systematic
; 
 ? 
;
_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                 94.720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.170(2)
_cell_length_b                   12.496(2)
_cell_length_c                   23.338(3)
_cell_measurement_temperature    293(2)
_cell_volume                     2665.2(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6145
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4662
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0929P)²+1.8963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1708
_reflns_number_gt                3463
_reflns_number_total             4662
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401514d_si_001.cif
_cod_data_source_block           z2
_cod_database_code               4028772
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 0.28421(8) 0.20933(6) 0.12145(3) 0.0378(2) Uani 1 1 d . . .
P2 P 0.61145(9) 0.20324(8) 0.15488(3) 0.0460(3) Uani 1 1 d D . .
O3 O 0.7329(2) 0.29247(19) 0.15119(11) 0.0552(6) Uani 1 1 d . A .
C1 C 0.3916(3) 0.3037(2) 0.00628(12) 0.0356(6) Uani 1 1 d . A .
C3 C 0.1745(3) 0.2698(2) 0.06309(12) 0.0370(7) Uani 1 1 d . . .
C2 C 0.2350(3) 0.3086(2) 0.01336(12) 0.0360(6) Uani 1 1 d . . .
C10 C 0.4512(3) 0.3357(2) -0.04902(12) 0.0365(6) Uani 1 1 d . . .
C4 C 0.0231(3) 0.2793(3) 0.06884(15) 0.0493(8) Uani 1 1 d . . .
H4A H -0.0158 0.2532 0.1017 0.059 Uiso 1 1 calc R . .
C11 C 0.5666(3) 0.4080(2) -0.04991(13) 0.0412(7) Uani 1 1 d . . .
H11A H 0.6042 0.4394 -0.0157 0.049 Uiso 1 1 calc R . .
C22 C 0.2284(3) 0.2630(3) 0.18895(13) 0.0423(7) Uani 1 1 d . . .
C9 C 0.4879(3) 0.2739(2) 0.05074(12) 0.0388(7) Uani 1 1 d . . .
H9A H 0.5859 0.2768 0.0433 0.047 Uiso 1 1 calc R A .
C15 C 0.3968(4) 0.2916(3) -0.10164(13) 0.0458(7) Uani 1 1 d . . .
H15A H 0.3188 0.2439 -0.1026 0.055 Uiso 1 1 calc R . .
C16 C 0.2422(3) 0.0672(3) 0.12390(14) 0.0453(7) Uani 1 1 d . . .
C7 C 0.1376(3) 0.3584(3) -0.02857(14) 0.0471(8) Uani 1 1 d . . .
H7A H 0.1738 0.3862 -0.0615 0.057 Uiso 1 1 calc R . .
C6 C -0.0093(4) 0.3667(3) -0.02178(16) 0.0571(9) Uani 1 1 d . . .
H6A H -0.0709 0.3999 -0.0501 0.068 Uiso 1 1 calc R . .
C8 C 0.4615(3) 0.2386(3) 0.10739(12) 0.0407(7) Uani 1 1 d . A .
C12 C 0.6267(3) 0.4341(3) -0.10081(13) 0.0462(8) Uani 1 1 d . . .
H12A H 0.7042 0.4822 -0.1004 0.055 Uiso 1 1 calc R . .
C23 C 0.2853(4) 0.3593(3) 0.20849(14) 0.0509(8) Uani 1 1 d . . .
H23A H 0.3578 0.3921 0.1891 0.061 Uiso 1 1 calc R . .
C5 C -0.0665(4) 0.3262(3) 0.02675(17) 0.0602(10) Uani 1 1 d . . .
H5A H -0.1664 0.3310 0.0306 0.072 Uiso 1 1 calc R . .
C21 C 0.3068(4) 0.0026(3) 0.16709(17) 0.0621(10) Uani 1 1 d . . .
H21A H 0.3648 0.0333 0.1973 0.075 Uiso 1 1 calc R . .
C14 C 0.4576(4) 0.3178(3) -0.15252(13) 0.0499(8) Uani 1 1 d . . .
H14A H 0.4205 0.2870 -0.1870 0.060 Uiso 1 1 calc R . .
C27 C 0.1186(4) 0.2144(3) 0.21717(16) 0.0569(9) Uani 1 1 d . . .
H27A H 0.0785 0.1498 0.2040 0.068 Uiso 1 1 calc R . .
C17 C 0.1533(4) 0.0196(3) 0.08044(17) 0.0617(10) Uani 1 1 d . . .
H17A H 0.1075 0.0613 0.0513 0.074 Uiso 1 1 calc R . .
C13 C 0.5715(4) 0.3887(3) -0.15224(13) 0.0497(8) Uani 1 1 d . . .
H13A H 0.6116 0.4063 -0.1863 0.060 Uiso 1 1 calc R . .
C26 C 0.0694(5) 0.2636(4) 0.26547(17) 0.0701(11) Uani 1 1 d . . .
H26A H -0.0037 0.2314 0.2848 0.084 Uiso 1 1 calc R . .
C24 C 0.2365(4) 0.4080(3) 0.25659(15) 0.0625(10) Uani 1 1 d . . .
H24A H 0.2761 0.4727 0.2699 0.075 Uiso 1 1 calc R . .
C25 C 0.1276(4) 0.3584(4) 0.28445(16) 0.0688(11) Uani 1 1 d . . .
H25A H 0.0936 0.3906 0.3167 0.083 Uiso 1 1 calc R . .
C20 C 0.2861(5) -0.1069(3) 0.16582(19) 0.0709(11) Uani 1 1 d . . .
H20A H 0.3313 -0.1493 0.1948 0.085 Uiso 1 1 calc R . .
C19 C 0.2003(5) -0.1529(3) 0.1225(2) 0.0766(12) Uani 1 1 d . . .
H19A H 0.1879 -0.2268 0.1216 0.092 Uiso 1 1 calc R . .
C18 C 0.1323(5) -0.0910(3) 0.0803(2) 0.0811(13) Uani 1 1 d . . .
H18A H 0.0715 -0.1227 0.0513 0.097 Uiso 1 1 calc R . .
C29 C 0.8370(5) 0.4650(4) 0.1726(2) 0.0842(13) Uani 1 1 d . A .
H29A H 0.8141 0.5373 0.1825 0.126 Uiso 1 1 calc R . .
H29B H 0.8837 0.4645 0.1373 0.126 Uiso 1 1 calc R . .
H29C H 0.9016 0.4344 0.2027 0.126 Uiso 1 1 calc R . .
C28 C 0.7035(5) 0.4027(4) 0.1657(2) 0.0862(14) Uani 1 1 d . . .
H28A H 0.6380 0.4341 0.1355 0.103 Uiso 1 1 calc R A .
H28B H 0.6552 0.4048 0.2011 0.103 Uiso 1 1 calc R . .
O1 O 0.5685(8) 0.1652(6) 0.21072(19) 0.0634(16) Uani 0.746(10) 1 d PD A 1
O2 O 0.7023(6) 0.1157(4) 0.1233(3) 0.0581(15) Uani 0.746(10) 1 d PD A 1
C30 C 0.6396(6) 0.0176(4) 0.0993(2) 0.0655(18) Uani 0.746(10) 1 d PD A 1
H30A H 0.6468 -0.0381 0.1283 0.079 Uiso 0.746(10) 1 calc PR A 1
H30B H 0.5368 0.0287 0.0874 0.079 Uiso 0.746(10) 1 calc PR A 1
C31 C 0.7156(12) -0.0152(8) 0.0506(4) 0.128(3) Uani 0.746(10) 1 d PDU A 1
H31A H 0.6677 -0.0766 0.0329 0.192 Uiso 0.746(10) 1 calc PR A 1
H31B H 0.8148 -0.0331 0.0632 0.192 Uiso 0.746(10) 1 calc PR A 1
H31C H 0.7148 0.0423 0.0233 0.192 Uiso 0.746(10) 1 calc PR A 1
O1' O 0.577(2) 0.2093(13) 0.2158(4) 0.053(4) Uani 0.254(10) 1 d PDU A 2
O2' O 0.706(2) 0.1022(12) 0.1429(6) 0.060(5) Uani 0.254(10) 1 d PDU A 2
C30' C 0.711(2) 0.0721(19) 0.0840(7) 0.097(7) Uani 0.254(10) 1 d PDU A 2
H30C H 0.8065 0.0405 0.0812 0.117 Uiso 0.254(10) 1 calc PR A 2
H30D H 0.7107 0.1388 0.0627 0.117 Uiso 0.254(10) 1 calc PR A 2
C31' C 0.609(2) 0.003(2) 0.0513(11) 0.098(7) Uani 0.254(10) 1 d PDU A 2
H31D H 0.6571 -0.0297 0.0207 0.147 Uiso 0.254(10) 1 calc PR A 2
H31E H 0.5273 0.0444 0.0354 0.147 Uiso 0.254(10) 1 calc PR A 2
H31F H 0.5754 -0.0514 0.0760 0.147 Uiso 0.254(10) 1 calc PR A 2
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
C8 P1 C3 104.18(14)
C8 P1 C16 114.74(15)
C3 P1 C16 109.18(15)
C8 P1 C22 114.98(15)
C3 P1 C22 108.75(14)
C16 P1 C22 104.89(15)
O1 P2 O2' 95.2(6)
O1 P2 O3 121.1(3)
O2' P2 O3 98.9(9)
O1 P2 O2 112.1(3)
O2' P2 O2 17.7(6)
O3 P2 O2 93.5(3)
O1 P2 O1' 22.1(6)
O2' P2 O1' 112.1(9)
O3 P2 O1' 102.9(7)
O2 P2 O1' 129.8(7)
O1 P2 C8 112.9(3)
O2' P2 C8 120.5(6)
O3 P2 C8 107.89(14)
O2 P2 C8 107.1(2)
O1' P2 C8 112.0(8)
C28 O3 P2 120.8(2)
C9 C1 C2 120.6(3)
C9 C1 C10 118.2(2)
C2 C1 C10 121.2(2)
C4 C3 C2 120.4(3)
C4 C3 P1 117.3(2)
C2 C3 P1 122.4(2)
C3 C2 C7 116.8(3)
C3 C2 C1 122.3(3)
C7 C2 C1 120.7(3)
C11 C10 C15 117.3(3)
C11 C10 C1 121.2(3)
C15 C10 C1 121.4(3)
C5 C4 C3 120.5(3)
C12 C11 C10 121.4(3)
C23 C22 C27 119.8(3)
C23 C22 P1 118.9(2)
C27 C22 P1 121.0(3)
C1 C9 C8 129.9(3)
C14 C15 C10 121.1(3)
C17 C16 C21 118.3(3)
C17 C16 P1 120.7(3)
C21 C16 P1 120.8(3)
C6 C7 C2 121.6(3)
C7 C6 C5 120.5(3)
C9 C8 P1 118.3(2)
C9 C8 P2 118.6(2)
P1 C8 P2 122.00(17)
C13 C12 C11 120.2(3)
C22 C23 C24 121.0(3)
C4 C5 C6 120.2(3)
C20 C21 C16 120.8(4)
C13 C14 C15 120.5(3)
C22 C27 C26 119.2(4)
C16 C17 C18 120.0(4)
C14 C13 C12 119.5(3)
C25 C26 C27 120.3(4)
C25 C24 C23 118.6(4)
C26 C25 C24 121.1(3)
C19 C20 C21 120.4(4)
C20 C19 C18 120.0(4)
C19 C18 C17 120.4(4)
C29 C28 O3 111.4(4)
C30 O2 P2 123.7(5)
C31 C30 O2 110.1(6)
C30' O2' P2 116.2(13)
O2' C30' C31' 127(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C8 1.724(3)
P1 C3 1.792(3)
P1 C16 1.819(3)
P1 C22 1.824(3)
P2 O1 1.471(4)
P2 O2' 1.571(9)
P2 O3 1.583(3)
P2 O2 1.592(4)
P2 O1' 1.483(8)
P2 C8 1.751(3)
O3 C28 1.449(5)
C1 C9 1.358(4)
C1 C2 1.461(4)
C1 C10 1.497(4)
C3 C4 1.411(4)
C3 C2 1.412(4)
C2 C7 1.414(4)
C10 C11 1.393(4)
C10 C15 1.400(4)
C4 C5 1.360(5)
C11 C12 1.389(4)
C22 C23 1.373(5)
C22 C27 1.387(5)
C9 C8 1.433(4)
C15 C14 1.392(5)
C16 C17 1.383(5)
C16 C21 1.386(5)
C7 C6 1.373(5)
C6 C5 1.383(5)
C12 C13 1.385(5)
C23 C24 1.384(5)
C21 C20 1.381(6)
C14 C13 1.370(5)
C27 C26 1.391(5)
C17 C18 1.396(6)
C26 C25 1.360(6)
C24 C25 1.382(6)
C20 C19 1.357(6)
C19 C18 1.361(6)
C29 C28 1.448(6)
O2 C30 1.447(6)
C30 C31 1.440(7)
O2' C30' 1.430(11)
C30' C31' 1.442(11)
