##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL
_journal_date_recd_electronic     2008-05-04
_journal_date_accepted     2008-06-16
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2008
_journal_volume     64
_journal_issue      7
_journal_page_first     o405
_journal_page_last     o410
_journal_paper_category     FO
_journal_coeditor_code     AV3152
_publ_contact_author_name     'Fernando Castañeda'
_publ_contact_author_address
;
Departamento de Química Orgánica y Fisicoquímica
Facultad de Ciencias Químicas y Farmacéuticas
Universidad de Chile
Casilla 233
Santiago
Chile
;
_publ_contact_author_email     fcastane@ciq.uchile.cl
_publ_contact_author_fax     56-2-696_7359
_publ_contact_author_phone     56-2-678_4519
_publ_section_title
;
Favoured conformations of methyl isopropyl, ethyl isopropyl, methyl
tert-butyl, and ethyl tert-butyl
2-(triphenylphosphoranyliden)malonate
;
loop_
    _publ_author_name
    _publ_author_address
    "Fernando Castañeda"
;
Departamento de Química Orgánica y Fisicoquímica
Facultad de Ciencias Químicas y Farmacéuticas
Universidad de Chile
Casilla 233
Santiago
Chile
;
    "Paul Silva"
;
Departamento de Química Orgánica y Fisicoquímica
Facultad de Ciencias Químicas y Farmacéuticas
Universidad de Chile
Casilla 233
Santiago
Chile
;
    "Clifford A. Bunton"
;
Department of Chemistry and Biochemistry
University of California
Santa Barbara
CA 93106
USA
;
    "María Teresa Garland"
;
CIMAT
Departamento de Física
Facultad de Ciencias Físicas y Matemáticas
Universidad de Chile
Casilla 487-3
Santiago de Chile
Chile
;
    "Ricardo Baggio"
;
Departamento de Física
Comisión Nacional de Energía Atómica
Avenida Gral Paz 1499
1650 Buenos Aires
Argentina
;
_exptl_special_details
;
Methyl isopropyl 2-triphenylphosphoranylidene malonate, (Ia).
¹H NMR (CDCl₃, δ, p.p.m.): 0.70 (d, 6H), 3.40 (s, 3H), 4.75 (m, 1H),
7.3--8.0 (m, 15H); IR (KBr): 1678, 1638 cm⁻¹.
Ethyl isopropyl 2-triphenylphosphoranylidene malonate, (Ib).
¹H NMR (CDCl₃, δ, p.p.m.): 0.76 (d, 6H), 0.88 (t, 3H, J = 7.2 Hz),
3.86 (q, 2H, J = 7.2 Hz), 7.3--8.0 (m, 15H); IR (KBr): 1678, 1612 cm⁻¹.
Methyl tert-butyl 2-triphenylphosphoranylidene malonate, (IIa).
¹H NMR (CDCl₃, δ, p.p.m.): 0.98 (d, 9H), 3.45 (s, 3H), 7.3--8.1 (m, 15H);
IR (KBr): 1667, 1649 cm⁻¹.
Ethyl tert-butyl 2-triphenylphosphoranylidene malonate, (IIb).
¹H NMR (CDCl₃, δ, p.p.m.): 0.88 (t, 3H, J = 7.2 Hz), 1.04 (s,9H), 3.86
(q, 2H, J = 7.2 Hz), 7.2--8.0 (m, 15H); IR (KBr): 1678, 1613 cm⁻¹.
;
data_Ia
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
methyl isopropyl 2-(triphenylphosphoranyliden)malonate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C25 H25 O4 P'
_chemical_formula_sum     'C25 H25 O4 P'
_chemical_formula_iupac     'C25 H25 O4 P'
_chemical_formula_weight     420.42
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.8033(6)
_cell_length_b     10.4492(7)
_cell_length_c     11.2169(7)
_cell_angle_alpha     100.573(2)
_cell_angle_beta     94.878(2)
_cell_angle_gamma     102.446(3)
_cell_volume     1093.64(12)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1718
_cell_measurement_theta_min     2.46
_cell_measurement_theta_max     21.88
_cell_measurement_temperature     273(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.17
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.277
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     444
_exptl_absorpt_coefficient_mu     0.154
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     273(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9176
_diffrn_reflns_av_R_equivalents     0.0249
_diffrn_reflns_av_sigmaI/netI     0.0480
_diffrn_reflns_theta_min     1.86
_diffrn_reflns_theta_max     27.76
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.904
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     4675
_reflns_number_gt     3133
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0820
_refine_ls_R_factor_gt     0.0523
_refine_ls_wR_factor_gt     0.1181
_refine_ls_wR_factor_ref     0.1338
_refine_ls_goodness_of_fit_ref     1.014
_refine_ls_restrained_S_all     1.014
_refine_ls_number_reflns     4675
_refine_ls_number_parameters     282
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0646P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.273
_refine_diff_density_min     -0.169
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART-NT (Bruker, 2001)'
_computing_cell_refinement     'SAINT-NT (Bruker, 2001)'
_computing_data_reduction     'SAINT-NT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL-NT (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL-NT (Sheldrick, 2008) and PLATON (Spek, 2003)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    P P1 0.15100(5) 0.32873(5) 0.22639(5) 0.04233(17) Uani d . 1 . .
    O O1 0.37276(15) 0.23368(13) 0.12939(14) 0.0538(4) Uani d . 1 . .
    O O2 0.36216(19) 0.04992(16) 0.20754(18) 0.0788(6) Uani d . 1 . .
    O O3 0.2072(16) 0.0425(8) 0.3867(10) 0.0620(16) Uani d PD 0.66(2) A 1
    C C7 0.1996(15) 0.0002(13) 0.5010(12) 0.067(2) Uani d PD 0.66(2) A 1
    H H7A 0.2688 -0.0506 0.5119 0.101 Uiso calc PR 0.66(2) A 1
    H H7B 0.1074 -0.0545 0.5011 0.101 Uiso calc PR 0.66(2) A 1
    H H7C 0.2175 0.0774 0.5666 0.101 Uiso calc PR 0.66(2) A 1
    O O3' 0.221(3) 0.0571(15) 0.4171(15) 0.0620(16) Uani d PD 0.34(2) A 2
    C C7' 0.189(3) 0.022(3) 0.5312(17) 0.067(2) Uani d PD 0.34(2) A 2
    H H7'A 0.1025 0.0448 0.5505 0.101 Uiso calc PR 0.34(2) A 2
    H H7'B 0.2640 0.0703 0.5947 0.101 Uiso calc PR 0.34(2) A 2
    H H7'C 0.1793 -0.0725 0.5246 0.101 Uiso calc PR 0.34(2) A 2
    O O4 0.14402(17) 0.23495(16) 0.46638(14) 0.0638(4) Uani d . 1 A .
    C C1 0.2189(2) 0.20166(19) 0.27093(19) 0.0444(5) Uani d . 1 A .
    C C2 0.3203(2) 0.1497(2) 0.2025(2) 0.0510(5) Uani d . 1 . .
    C C3 0.1872(2) 0.1672(2) 0.3853(2) 0.0490(5) Uani d D 1 . .
    C C4 0.4666(2) 0.1924(2) 0.0455(2) 0.0575(6) Uani d . 1 . .
    H H4 0.5222 0.1391 0.0827 0.069 Uiso calc R 1 . .
    C C5 0.3833(3) 0.1088(3) -0.0698(3) 0.0808(8) Uani d . 1 . .
    H H5A 0.3202 0.0327 -0.0520 0.121 Uiso calc R 1 . .
    H H5B 0.4458 0.0787 -0.1241 0.121 Uiso calc R 1 . .
    H H5C 0.3299 0.1608 -0.1078 0.121 Uiso calc R 1 . .
    C C6 0.5634(3) 0.3176(3) 0.0289(3) 0.0889(9) Uani d . 1 . .
    H H6A 0.5101 0.3695 -0.0096 0.133 Uiso calc R 1 . .
    H H6B 0.6325 0.2948 -0.0216 0.133 Uiso calc R 1 . .
    H H6C 0.6098 0.3691 0.1073 0.133 Uiso calc R 1 . .
    C C11 0.2649(2) 0.49492(19) 0.27479(18) 0.0438(5) Uani d . 1 . .
    C C12 0.3953(2) 0.5102(2) 0.3400(2) 0.0540(6) Uani d . 1 . .
    H H12 0.4224 0.4358 0.3598 0.065 Uiso calc R 1 . .
    C C13 0.4854(3) 0.6352(3) 0.3759(2) 0.0692(7) Uani d . 1 . .
    H H13 0.5739 0.6448 0.4184 0.083 Uiso calc R 1 . .
    C C14 0.4447(3) 0.7456(2) 0.3490(3) 0.0728(7) Uani d . 1 . .
    H H14 0.5053 0.8299 0.3745 0.087 Uiso calc R 1 . .
    C C15 0.3155(3) 0.7322(2) 0.2850(2) 0.0666(7) Uani d . 1 . .
    H H15 0.2883 0.8074 0.2677 0.080 Uiso calc R 1 . .
    C C16 0.2259(2) 0.6077(2) 0.2464(2) 0.0534(6) Uani d . 1 . .
    H H16 0.1391 0.5985 0.2012 0.064 Uiso calc R 1 . .
    C C21 -0.0163(2) 0.3286(2) 0.28335(18) 0.0449(5) Uani d . 1 . .
    C C22 -0.0486(2) 0.4440(2) 0.3444(2) 0.0534(6) Uani d . 1 . .
    H H22 0.0186 0.5248 0.3597 0.064 Uiso calc R 1 . .
    C C23 -0.1797(3) 0.4405(3) 0.3830(2) 0.0640(7) Uani d . 1 . .
    H H23 -0.1998 0.5183 0.4247 0.077 Uiso calc R 1 . .
    C C24 -0.2795(3) 0.3221(3) 0.3595(2) 0.0654(7) Uani d . 1 . .
    H H24 -0.3682 0.3202 0.3837 0.079 Uiso calc R 1 . .
    C C25 -0.2496(2) 0.2072(3) 0.3011(2) 0.0623(6) Uani d . 1 . .
    H H25 -0.3178 0.1271 0.2862 0.075 Uiso calc R 1 . .
    C C26 -0.1183(2) 0.2088(2) 0.2637(2) 0.0552(6) Uani d . 1 . .
    H H26 -0.0983 0.1295 0.2252 0.066 Uiso calc R 1 . .
    C C31 0.1138(2) 0.29891(19) 0.06101(18) 0.0436(5) Uani d . 1 . .
    C C32 0.0160(2) 0.1853(2) -0.0032(2) 0.0598(6) Uani d . 1 . .
    H H32 -0.0332 0.1261 0.0395 0.072 Uiso calc R 1 . .
    C C33 -0.0098(3) 0.1588(3) -0.1287(2) 0.0678(7) Uani d . 1 . .
    H H33 -0.0768 0.0827 -0.1698 0.081 Uiso calc R 1 . .
    C C34 0.0622(3) 0.2432(3) -0.1932(2) 0.0646(7) Uani d . 1 . .
    H H34 0.0456 0.2244 -0.2782 0.078 Uiso calc R 1 . .
    C C35 0.1591(3) 0.3557(2) -0.1321(2) 0.0668(7) Uani d . 1 . .
    H H35 0.2080 0.4140 -0.1757 0.080 Uiso calc R 1 . .
    C C36 0.1851(2) 0.3833(2) -0.0061(2) 0.0574(6) Uani d . 1 . .
    H H36 0.2517 0.4601 0.0342 0.069 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    P1 C1 . 1.7388(19) y
    P1 C11 . 1.809(2) ?
    P1 C21 . 1.810(2) ?
    P1 C31 . 1.815(2) ?
    O1 C2 . 1.360(2) ?
    O1 C4 . 1.445(3) ?
    O2 C2 . 1.208(2) y
    O3 C3 . 1.362(4) ?
    O3 C7 . 1.434(5) ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    O3' C3 . 1.361(7) ?
    O3' C7' . 1.435(8) ?
    C7' H7'A . 0.9600 ?
    C7' H7'B . 0.9600 ?
    C7' H7'C . 0.9600 ?
    O4 C3 . 1.211(2) y
    C1 C3 . 1.436(3) y
    C1 C2 . 1.443(3) y
    C4 C5 . 1.483(3) ?
    C4 C6 . 1.494(3) ?
    C4 H4 . 0.9800 ?
    C5 H5A . 0.9600 ?
    C5 H5B . 0.9600 ?
    C5 H5C . 0.9600 ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
    C11 C12 . 1.380(3) ?
    C11 C16 . 1.395(3) ?
    C12 C13 . 1.377(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.374(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.368(4) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.374(3) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C21 C22 . 1.386(3) ?
    C21 C26 . 1.392(3) ?
    C22 C23 . 1.385(3) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.368(3) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.361(3) ?
    C24 H24 . 0.9300 ?
    C25 C26 . 1.385(3) ?
    C25 H25 . 0.9300 ?
    C26 H26 . 0.9300 ?
    C31 C36 . 1.378(3) ?
    C31 C32 . 1.388(3) ?
    C32 C33 . 1.374(3) ?
    C32 H32 . 0.9300 ?
    C33 C34 . 1.361(3) ?
    C33 H33 . 0.9300 ?
    C34 C35 . 1.366(3) ?
    C34 H34 . 0.9300 ?
    C35 C36 . 1.379(3) ?
    C35 H35 . 0.9300 ?
    C36 H36 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 P1 C11 . . 114.92(9) ?
    C1 P1 C21 . . 109.49(9) ?
    C11 P1 C21 . . 108.93(9) ?
    C1 P1 C31 . . 110.74(9) ?
    C11 P1 C31 . . 106.43(9) ?
    C21 P1 C31 . . 105.91(9) ?
    C2 O1 C4 . . 118.34(16) ?
    C3 O3 C7 . . 116.3(7) ?
    C3 O3' C7' . . 120.6(18) ?
    O3' C7' H7'A . . 109.5 ?
    O3' C7' H7'B . . 109.5 ?
    H7'A C7' H7'B . . 109.5 ?
    O3' C7' H7'C . . 109.5 ?
    H7'A C7' H7'C . . 109.5 ?
    H7'B C7' H7'C . . 109.5 ?
    C3 C1 C2 . . 122.36(18) ?
    C3 C1 P1 . . 117.71(15) ?
    C2 C1 P1 . . 119.26(15) ?
    O2 C2 O1 . . 121.2(2) ?
    O2 C2 C1 . . 128.4(2) ?
    O1 C2 C1 . . 110.30(17) ?
    O4 C3 O3' . . 113.3(8) ?
    O4 C3 O3 . . 124.7(5) ?
    O4 C3 C1 . . 126.00(19) ?
    O3' C3 C1 . . 120.3(9) ?
    O3 C3 C1 . . 109.2(5) ?
    O1 C4 C5 . . 109.69(18) ?
    O1 C4 C6 . . 106.54(19) ?
    C5 C4 C6 . . 113.9(2) ?
    O1 C4 H4 . . 108.9 ?
    C5 C4 H4 . . 108.9 ?
    C6 C4 H4 . . 108.9 ?
    C4 C5 H5A . . 109.5 ?
    C4 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    C4 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    C4 C6 H6A . . 109.5 ?
    C4 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C4 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    C12 C11 C16 . . 119.1(2) ?
    C12 C11 P1 . . 118.92(16) ?
    C16 C11 P1 . . 121.99(16) ?
    C13 C12 C11 . . 120.2(2) ?
    C13 C12 H12 . . 119.9 ?
    C11 C12 H12 . . 119.9 ?
    C14 C13 C12 . . 120.1(2) ?
    C14 C13 H13 . . 120.0 ?
    C12 C13 H13 . . 120.0 ?
    C15 C14 C13 . . 120.4(2) ?
    C15 C14 H14 . . 119.8 ?
    C13 C14 H14 . . 119.8 ?
    C14 C15 C16 . . 120.0(2) ?
    C14 C15 H15 . . 120.0 ?
    C16 C15 H15 . . 120.0 ?
    C15 C16 C11 . . 120.2(2) ?
    C15 C16 H16 . . 119.9 ?
    C11 C16 H16 . . 119.9 ?
    C22 C21 C26 . . 118.1(2) ?
    C22 C21 P1 . . 122.64(17) ?
    C26 C21 P1 . . 119.22(16) ?
    C23 C22 C21 . . 120.9(2) ?
    C23 C22 H22 . . 119.5 ?
    C21 C22 H22 . . 119.5 ?
    C24 C23 C22 . . 119.8(2) ?
    C24 C23 H23 . . 120.1 ?
    C22 C23 H23 . . 120.1 ?
    C25 C24 C23 . . 120.4(2) ?
    C25 C24 H24 . . 119.8 ?
    C23 C24 H24 . . 119.8 ?
    C24 C25 C26 . . 120.5(2) ?
    C24 C25 H25 . . 119.8 ?
    C26 C25 H25 . . 119.8 ?
    C25 C26 C21 . . 120.3(2) ?
    C25 C26 H26 . . 119.9 ?
    C21 C26 H26 . . 119.9 ?
    C36 C31 C32 . . 117.4(2) ?
    C36 C31 P1 . . 122.03(16) ?
    C32 C31 P1 . . 120.52(16) ?
    C33 C32 C31 . . 121.3(2) ?
    C33 C32 H32 . . 119.4 ?
    C31 C32 H32 . . 119.4 ?
    C34 C33 C32 . . 120.4(2) ?
    C34 C33 H33 . . 119.8 ?
    C32 C33 H33 . . 119.8 ?
    C33 C34 C35 . . 119.4(2) ?
    C33 C34 H34 . . 120.3 ?
    C35 C34 H34 . . 120.3 ?
    C34 C35 C36 . . 120.5(2) ?
    C34 C35 H35 . . 119.7 ?
    C36 C35 H35 . . 119.7 ?
    C31 C36 C35 . . 121.0(2) ?
    C31 C36 H36 . . 119.5 ?
    C35 C36 H36 . . 119.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C11 P1 C1 C3 . . . . 91.24(18) ?
    C21 P1 C1 C3 . . . . -31.72(19) ?
    C31 P1 C1 C3 . . . . -148.13(16) ?
    C11 P1 C1 C2 . . . . -79.61(19) ?
    C21 P1 C1 C2 . . . . 157.44(16) ?
    C31 P1 C1 C2 . . . . 41.02(19) ?
    C4 O1 C2 O2 . . . . 8.0(3) ?
    C4 O1 C2 C1 . . . . -174.49(17) ?
    C3 C1 C2 O2 . . . . 22.0(4) ?
    P1 C1 C2 O2 . . . . -167.6(2) ?
    C3 C1 C2 O1 . . . . -155.35(19) ?
    P1 C1 C2 O1 . . . . 15.0(2) ?
    C7' O3' C3 O4 . . . . 7(3) ?
    C7' O3' C3 O3 . . . . -136(10) ?
    C7' O3' C3 C1 . . . . -180(2) ?
    C7 O3 C3 O4 . . . . -11.2(16) ?
    C7 O3 C3 O3' . . . . 30(7) ?
    C7 O3 C3 C1 . . . . 171.4(10) ?
    C2 C1 C3 O4 . . . . 153.5(2) ?
    P1 C1 C3 O4 . . . . -17.0(3) ?
    C2 C1 C3 O3' . . . . -18.5(15) ?
    P1 C1 C3 O3' . . . . 171.0(15) ?
    C2 C1 C3 O3 . . . . -29.1(8) ?
    P1 C1 C3 O3 . . . . 160.3(7) ?
    C2 O1 C4 C5 . . . . 85.8(2) ?
    C2 O1 C4 C6 . . . . -150.5(2) ?
    C1 P1 C11 C12 . . . . 1.1(2) ?
    C21 P1 C11 C12 . . . . 124.33(17) ?
    C31 P1 C11 C12 . . . . -121.88(17) ?
    C1 P1 C11 C16 . . . . 179.97(17) ?
    C21 P1 C11 C16 . . . . -56.78(19) ?
    C31 P1 C11 C16 . . . . 57.00(19) ?
    C16 C11 C12 C13 . . . . -0.2(3) ?
    P1 C11 C12 C13 . . . . 178.70(17) ?
    C11 C12 C13 C14 . . . . 1.3(4) ?
    C12 C13 C14 C15 . . . . -0.9(4) ?
    C13 C14 C15 C16 . . . . -0.5(4) ?
    C14 C15 C16 C11 . . . . 1.6(4) ?
    C12 C11 C16 C15 . . . . -1.2(3) ?
    P1 C11 C16 C15 . . . . 179.91(17) ?
    C1 P1 C21 C22 . . . . 131.52(18) ?
    C11 P1 C21 C22 . . . . 5.1(2) ?
    C31 P1 C21 C22 . . . . -109.04(18) ?
    C1 P1 C21 C26 . . . . -49.68(19) ?
    C11 P1 C21 C26 . . . . -176.12(16) ?
    C31 P1 C21 C26 . . . . 69.76(18) ?
    C26 C21 C22 C23 . . . . -1.0(3) ?
    P1 C21 C22 C23 . . . . 177.79(16) ?
    C21 C22 C23 C24 . . . . -0.7(3) ?
    C22 C23 C24 C25 . . . . 1.6(4) ?
    C23 C24 C25 C26 . . . . -0.6(4) ?
    C24 C25 C26 C21 . . . . -1.2(3) ?
    C22 C21 C26 C25 . . . . 2.0(3) ?
    P1 C21 C26 C25 . . . . -176.85(16) ?
    C1 P1 C31 C36 . . . . -115.23(18) ?
    C11 P1 C31 C36 . . . . 10.3(2) ?
    C21 P1 C31 C36 . . . . 126.16(18) ?
    C1 P1 C31 C32 . . . . 61.69(19) ?
    C11 P1 C31 C32 . . . . -172.75(17) ?
    C21 P1 C31 C32 . . . . -56.92(19) ?
    C36 C31 C32 C33 . . . . -0.6(3) ?
    P1 C31 C32 C33 . . . . -177.64(18) ?
    C31 C32 C33 C34 . . . . 0.9(4) ?
    C32 C33 C34 C35 . . . . -0.9(4) ?
    C33 C34 C35 C36 . . . . 0.6(4) ?
    C32 C31 C36 C35 . . . . 0.3(3) ?
    P1 C31 C36 C35 . . . . 177.29(17) ?
    C34 C35 C36 C31 . . . . -0.3(4) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    P1 . O1 . . . 2.799(2) .
    P1 . O4 . . . 3.030(2) .
    C5 H5C Cg3 . 0.96 2.89 3.657(3) 138
    C23 H23 O4 2_566 0.93 2.56 3.430(3) 156
data_Ib
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
ethyl isopropyl 2-(triphenylphosphoranyliden)malonate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C26 H27 O4 P'
_chemical_formula_sum     'C26 H27 O4 P'
_chemical_formula_iupac     'C26 H27 O4 P'
_chemical_formula_weight     434.45
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c '
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     12.5175(16)
_cell_length_b     9.1555(12)
_cell_length_c     20.351(3)
_cell_angle_alpha     90.00
_cell_angle_beta     96.342(2)
_cell_angle_gamma     90.00
_cell_volume     2318.0(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1773
_cell_measurement_theta_min     2.43
_cell_measurement_theta_max     18.82
_cell_measurement_temperature     140(5)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.18
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.245
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     920
_exptl_absorpt_coefficient_mu     0.148
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     140(5)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19001
_diffrn_reflns_av_R_equivalents     0.0532
_diffrn_reflns_av_sigmaI/netI     0.0773
_diffrn_reflns_theta_min     2.01
_diffrn_reflns_theta_max     28.08
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.931
_diffrn_measured_fraction_theta_full     1.00
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     26
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     5252
_reflns_number_gt     2713
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1048
_refine_ls_R_factor_gt     0.0565
_refine_ls_wR_factor_gt     0.1255
_refine_ls_wR_factor_ref     0.1396
_refine_ls_goodness_of_fit_ref     0.856
_refine_ls_restrained_S_all     0.862
_refine_ls_number_reflns     5252
_refine_ls_number_parameters     300
_refine_ls_number_restraints     7
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0649P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.332
_refine_diff_density_min     -0.274
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART-NT (Bruker, 2001)'
_computing_cell_refinement     'SAINT-NT (Bruker, 2001)'
_computing_data_reduction     'SAINT-NT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL-NT (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL-NT (Sheldrick, 2008) and PLATON (Spek, 2003)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    P P1 0.73850(5) 0.02844(7) 0.17875(3) 0.0439(2) Uani d . 1 . .
    O O1 0.62126(16) 0.2614(2) 0.10059(10) 0.0973(8) Uani d . 1 . .
    O O2 0.73010(15) 0.2958(2) 0.02568(9) 0.0903(7) Uani d . 1 . .
    O O3 0.9224(3) 0.1642(6) 0.0498(2) 0.0647(15) Uani d PD 0.616(4) A 1
    O O3' 0.9339(5) 0.2182(8) 0.0701(4) 0.070(3) Uani d PD 0.384(4) A 2
    O O4 0.95195(13) 0.04885(19) 0.14924(9) 0.0686(5) Uani d . 1 A .
    C C1 0.77891(17) 0.1334(2) 0.11455(10) 0.0456(6) Uani d . 1 A .
    C C2 0.71144(19) 0.2344(3) 0.07458(12) 0.0510(6) Uani d . 1 . .
    C C3 0.8908(2) 0.1173(3) 0.10908(13) 0.0595(7) Uani d D 1 . .
    C C4 0.5427(2) 0.3578(4) 0.06629(17) 0.0883(10) Uani d . 1 . .
    H H4 0.5727 0.4019 0.0285 0.106 Uiso calc R 1 . .
    C C5 0.4466(3) 0.2731(4) 0.04265(18) 0.1286(14) Uani d . 1 . .
    H H5A 0.4660 0.1958 0.0144 0.193 Uiso calc R 1 . .
    H H5B 0.3950 0.3358 0.0184 0.193 Uiso calc R 1 . .
    H H5C 0.4159 0.2321 0.0797 0.193 Uiso calc R 1 . .
    C C6 0.5222(3) 0.4721(4) 0.11353(19) 0.1204(13) Uani d . 1 . .
    H H6A 0.5880 0.5221 0.1279 0.181 Uiso calc R 1 . .
    H H6B 0.4940 0.4289 0.1510 0.181 Uiso calc R 1 . .
    H H6C 0.4710 0.5405 0.0927 0.181 Uiso calc R 1 . .
    C C7 1.0358(3) 0.1456(6) 0.0431(3) 0.0897(17) Uani d PD 0.616(4) A 1
    H H7A 1.0459 0.1293 -0.0029 0.108 Uiso calc PR 0.616(4) A 1
    H H7B 1.0637 0.0615 0.0685 0.108 Uiso calc PR 0.616(4) A 1
    C C7' 1.0485(5) 0.2473(9) 0.0793(5) 0.0897(17) Uani d PD 0.384(4) A 2
    H H7'A 1.0751 0.2396 0.1258 0.108 Uiso calc PR 0.384(4) A 2
    H H7'B 1.0626 0.3455 0.0645 0.108 Uiso calc PR 0.384(4) A 2
    C C8 1.0953(6) 0.2825(8) 0.0683(4) 0.185(4) Uani d PD 0.616(4) A 1
    H H8A 1.0629 0.3663 0.0457 0.278 Uiso calc PR 0.616(4) A 1
    H H8B 1.1692 0.2756 0.0601 0.278 Uiso calc PR 0.616(4) A 1
    H H8C 1.0914 0.2923 0.1149 0.278 Uiso calc PR 0.616(4) A 1
    C C8' 1.1053(8) 0.1363(14) 0.0393(6) 0.185(4) Uani d PD 0.384(4) A 2
    H H8'A 1.0862 0.1536 -0.0070 0.278 Uiso calc PR 0.384(4) A 2
    H H8'B 1.0837 0.0394 0.0502 0.278 Uiso calc PR 0.384(4) A 2
    H H8'C 1.1817 0.1460 0.0496 0.278 Uiso calc PR 0.384(4) A 2
    C C11 0.78585(17) -0.1571(2) 0.17111(12) 0.0472(6) Uani d . 1 . .
    C C12 0.82857(19) -0.2374(3) 0.22506(12) 0.0571(7) Uani d . 1 . .
    H H12 0.8358 -0.1957 0.2670 0.069 Uiso calc R 1 . .
    C C13 0.8607(2) -0.3802(3) 0.21667(16) 0.0739(8) Uani d . 1 . .
    H H13 0.8901 -0.4339 0.2531 0.089 Uiso calc R 1 . .
    C C14 0.8498(2) -0.4429(3) 0.15545(18) 0.0774(9) Uani d . 1 . .
    H H14 0.8701 -0.5396 0.1503 0.093 Uiso calc R 1 . .
    C C15 0.8090(2) -0.3634(3) 0.10210(15) 0.0775(8) Uani d . 1 . .
    H H15 0.8021 -0.4059 0.0603 0.093 Uiso calc R 1 . .
    C C16 0.7780(2) -0.2208(3) 0.10917(13) 0.0622(7) Uani d . 1 . .
    H H16 0.7515 -0.1669 0.0722 0.075 Uiso calc R 1 . .
    C C21 0.78327(17) 0.0933(2) 0.26071(11) 0.0447(6) Uani d . 1 . .
    C C22 0.74220(18) 0.0353(3) 0.31610(11) 0.0544(6) Uani d . 1 . .
    H H22 0.6935 -0.0416 0.3109 0.065 Uiso calc R 1 . .
    C C23 0.7725(2) 0.0898(3) 0.37771(12) 0.0631(7) Uani d . 1 . .
    H H23 0.7435 0.0505 0.4140 0.076 Uiso calc R 1 . .
    C C24 0.8454(2) 0.2020(3) 0.38665(13) 0.0670(8) Uani d . 1 . .
    H H24 0.8656 0.2390 0.4287 0.080 Uiso calc R 1 . .
    C C25 0.8880(2) 0.2588(3) 0.33310(14) 0.0661(7) Uani d . 1 . .
    H H25 0.9383 0.3337 0.3389 0.079 Uiso calc R 1 . .
    C C26 0.85643(19) 0.2052(3) 0.27018(12) 0.0560(7) Uani d . 1 . .
    H H26 0.8851 0.2455 0.2340 0.067 Uiso calc R 1 . .
    C C31 0.59357(18) 0.0143(3) 0.17709(11) 0.0483(6) Uani d . 1 . .
    C C32 0.5370(2) -0.0903(3) 0.13930(14) 0.0718(8) Uani d . 1 . .
    H H32 0.5733 -0.1551 0.1144 0.086 Uiso calc R 1 . .
    C C33 0.4269(2) -0.1000(4) 0.13799(18) 0.0948(11) Uani d . 1 . .
    H H33 0.3892 -0.1696 0.1114 0.114 Uiso calc R 1 . .
    C C34 0.3730(2) -0.0081(4) 0.17536(19) 0.0952(11) Uani d . 1 . .
    H H34 0.2988 -0.0163 0.1750 0.114 Uiso calc R 1 . .
    C C35 0.4283(2) 0.0969(4) 0.21374(15) 0.0805(9) Uani d . 1 . .
    H H35 0.3919 0.1598 0.2394 0.097 Uiso calc R 1 . .
    C C36 0.5376(2) 0.1081(3) 0.21376(12) 0.0627(7) Uani d . 1 . .
    H H36 0.5747 0.1804 0.2390 0.075 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    P1 C1 . 1.741(2) y
    P1 C21 . 1.801(2) ?
    P1 C11 . 1.811(2) ?
    P1 C31 . 1.815(2) ?
    O1 C2 . 1.322(3) ?
    O1 C4 . 1.442(3) ?
    O2 C2 . 1.188(3) y
    O3 C3 . 1.379(4) ?
    O3 C7 . 1.451(3) ?
    O3' C3 . 1.367(7) ?
    O3' C7' . 1.451(3) ?
    O4 C3 . 1.228(3) y
    C1 C3 . 1.425(3) y
    C1 C2 . 1.441(3) y
    C4 C6 . 1.463(4) ?
    C4 C5 . 1.467(4) ?
    C4 H4 . 0.9800 ?
    C5 H5A . 0.9600 ?
    C5 H5B . 0.9600 ?
    C5 H5C . 0.9600 ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
    C7 C8 . 1.518(3) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C7' C8' . 1.526(3) ?
    C7' H7'A . 0.9700 ?
    C7' H7'B . 0.9700 ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C8' H8'A . 0.9600 ?
    C8' H8'B . 0.9600 ?
    C8' H8'C . 0.9600 ?
    C11 C12 . 1.379(3) ?
    C11 C16 . 1.382(3) ?
    C12 C13 . 1.384(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.365(4) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.359(4) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.375(3) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C21 C26 . 1.373(3) ?
    C21 C22 . 1.395(3) ?
    C22 C23 . 1.364(3) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.373(3) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.368(3) ?
    C24 H24 . 0.9300 ?
    C25 C26 . 1.387(3) ?
    C25 H25 . 0.9300 ?
    C26 H26 . 0.9300 ?
    C31 C32 . 1.375(3) ?
    C31 C36 . 1.378(3) ?
    C32 C33 . 1.379(4) ?
    C32 H32 . 0.9300 ?
    C33 C34 . 1.362(4) ?
    C33 H33 . 0.9300 ?
    C34 C35 . 1.377(4) ?
    C34 H34 . 0.9300 ?
    C35 C36 . 1.372(3) ?
    C35 H35 . 0.9300 ?
    C36 H36 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 P1 C21 . . 115.24(11) ?
    C1 P1 C11 . . 109.17(11) ?
    C21 P1 C11 . . 108.51(11) ?
    C1 P1 C31 . . 113.44(10) ?
    C21 P1 C31 . . 104.40(11) ?
    C11 P1 C31 . . 105.51(11) ?
    C2 O1 C4 . . 119.2(2) ?
    C3 O3 C7 . . 115.1(4) ?
    C3 O3' C7' . . 119.8(7) ?
    C3 C1 C2 . . 122.8(2) ?
    C3 C1 P1 . . 111.77(17) ?
    C2 C1 P1 . . 125.22(17) ?
    O2 C2 O1 . . 120.1(2) ?
    O2 C2 C1 . . 128.2(2) ?
    O1 C2 C1 . . 111.5(2) ?
    O4 C3 O3' . . 118.4(4) ?
    O4 C3 O3 . . 121.5(3) ?
    O4 C3 C1 . . 123.1(2) ?
    O3' C3 C1 . . 115.4(4) ?
    O3 C3 C1 . . 114.6(3) ?
    O1 C4 C6 . . 106.2(3) ?
    O1 C4 C5 . . 109.0(3) ?
    C6 C4 C5 . . 113.3(3) ?
    O1 C4 H4 . . 109.4 ?
    C6 C4 H4 . . 109.4 ?
    C5 C4 H4 . . 109.4 ?
    C4 C5 H5A . . 109.5 ?
    C4 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    C4 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    C4 C6 H6A . . 109.5 ?
    C4 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C4 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    O3 C7 C8 . . 108.7(4) ?
    O3 C7 H7A . . 110.0 ?
    C8 C7 H7A . . 110.0 ?
    O3 C7 H7B . . 110.0 ?
    C8 C7 H7B . . 110.0 ?
    H7A C7 H7B . . 108.3 ?
    O3' C7' C8' . . 108.7(6) ?
    O3' C7' H7'A . . 109.9 ?
    C8' C7' H7'A . . 109.9 ?
    O3' C7' H7'B . . 109.9 ?
    C8' C7' H7'B . . 109.9 ?
    H7'A C7' H7'B . . 108.3 ?
    C7' C8' H8'A . . 109.5 ?
    C7' C8' H8'B . . 109.5 ?
    H8'A C8' H8'B . . 109.5 ?
    C7' C8' H8'C . . 109.5 ?
    H8'A C8' H8'C . . 109.5 ?
    H8'B C8' H8'C . . 109.5 ?
    C12 C11 C16 . . 118.9(2) ?
    C12 C11 P1 . . 122.24(19) ?
    C16 C11 P1 . . 118.85(18) ?
    C11 C12 C13 . . 119.9(2) ?
    C11 C12 H12 . . 120.1 ?
    C13 C12 H12 . . 120.1 ?
    C14 C13 C12 . . 120.6(3) ?
    C14 C13 H13 . . 119.7 ?
    C12 C13 H13 . . 119.7 ?
    C15 C14 C13 . . 119.7(3) ?
    C15 C14 H14 . . 120.2 ?
    C13 C14 H14 . . 120.2 ?
    C14 C15 C16 . . 120.7(3) ?
    C14 C15 H15 . . 119.6 ?
    C16 C15 H15 . . 119.6 ?
    C15 C16 C11 . . 120.2(3) ?
    C15 C16 H16 . . 119.9 ?
    C11 C16 H16 . . 119.9 ?
    C26 C21 C22 . . 118.1(2) ?
    C26 C21 P1 . . 120.69(18) ?
    C22 C21 P1 . . 121.22(18) ?
    C23 C22 C21 . . 120.9(2) ?
    C23 C22 H22 . . 119.5 ?
    C21 C22 H22 . . 119.5 ?
    C22 C23 C24 . . 120.6(2) ?
    C22 C23 H23 . . 119.7 ?
    C24 C23 H23 . . 119.7 ?
    C25 C24 C23 . . 119.4(2) ?
    C25 C24 H24 . . 120.3 ?
    C23 C24 H24 . . 120.3 ?
    C24 C25 C26 . . 120.3(2) ?
    C24 C25 H25 . . 119.8 ?
    C26 C25 H25 . . 119.8 ?
    C21 C26 C25 . . 120.7(2) ?
    C21 C26 H26 . . 119.7 ?
    C25 C26 H26 . . 119.7 ?
    C32 C31 C36 . . 118.4(2) ?
    C32 C31 P1 . . 120.77(19) ?
    C36 C31 P1 . . 120.80(19) ?
    C31 C32 C33 . . 120.5(3) ?
    C31 C32 H32 . . 119.8 ?
    C33 C32 H32 . . 119.8 ?
    C34 C33 C32 . . 120.4(3) ?
    C34 C33 H33 . . 119.8 ?
    C32 C33 H33 . . 119.8 ?
    C33 C34 C35 . . 119.9(3) ?
    C33 C34 H34 . . 120.0 ?
    C35 C34 H34 . . 120.0 ?
    C36 C35 C34 . . 119.5(3) ?
    C36 C35 H35 . . 120.3 ?
    C34 C35 H35 . . 120.3 ?
    C35 C36 C31 . . 121.3(3) ?
    C35 C36 H36 . . 119.4 ?
    C31 C36 H36 . . 119.4 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C21 P1 C1 C3 . . . . 72.0(2) ?
    C11 P1 C1 C3 . . . . -50.4(2) ?
    C31 P1 C1 C3 . . . . -167.72(17) ?
    C21 P1 C1 C2 . . . . -103.2(2) ?
    C11 P1 C1 C2 . . . . 134.5(2) ?
    C31 P1 C1 C2 . . . . 17.1(2) ?
    C4 O1 C2 O2 . . . . 4.5(4) ?
    C4 O1 C2 C1 . . . . -178.6(2) ?
    C3 C1 C2 O2 . . . . 15.0(4) ?
    P1 C1 C2 O2 . . . . -170.4(2) ?
    C3 C1 C2 O1 . . . . -161.6(2) ?
    P1 C1 C2 O1 . . . . 13.0(3) ?
    C7' O3' C3 O4 . . . . -3.2(8) ?
    C7' O3' C3 O3 . . . . -107.7(12) ?
    C7' O3' C3 C1 . . . . 157.5(5) ?
    C7 O3 C3 O4 . . . . -8.6(6) ?
    C7 O3 C3 O3' . . . . 82.9(10) ?
    C7 O3 C3 C1 . . . . -178.8(3) ?
    C2 C1 C3 O4 . . . . 168.6(2) ?
    P1 C1 C3 O4 . . . . -6.7(3) ?
    C2 C1 C3 O3' . . . . 8.9(5) ?
    P1 C1 C3 O3' . . . . -166.4(4) ?
    C2 C1 C3 O3 . . . . -21.4(4) ?
    P1 C1 C3 O3 . . . . 163.3(3) ?
    C2 O1 C4 C6 . . . . -125.0(3) ?
    C2 O1 C4 C5 . . . . 112.5(3) ?
    C3 O3 C7 C8 . . . . -90.3(6) ?
    C3 O3' C7' C8' . . . . 85.6(10) ?
    C1 P1 C11 C12 . . . . 138.36(19) ?
    C21 P1 C11 C12 . . . . 12.0(2) ?
    C31 P1 C11 C12 . . . . -99.4(2) ?
    C1 P1 C11 C16 . . . . -42.3(2) ?
    C21 P1 C11 C16 . . . . -168.59(19) ?
    C31 P1 C11 C16 . . . . 80.0(2) ?
    C16 C11 C12 C13 . . . . -1.2(4) ?
    P1 C11 C12 C13 . . . . 178.16(19) ?
    C11 C12 C13 C14 . . . . -0.5(4) ?
    C12 C13 C14 C15 . . . . 1.4(4) ?
    C13 C14 C15 C16 . . . . -0.5(4) ?
    C14 C15 C16 C11 . . . . -1.3(4) ?
    C12 C11 C16 C15 . . . . 2.1(4) ?
    P1 C11 C16 C15 . . . . -177.3(2) ?
    C1 P1 C21 C26 . . . . -8.9(2) ?
    C11 P1 C21 C26 . . . . 113.87(19) ?
    C31 P1 C21 C26 . . . . -133.97(19) ?
    C1 P1 C21 C22 . . . . 168.92(18) ?
    C11 P1 C21 C22 . . . . -68.4(2) ?
    C31 P1 C21 C22 . . . . 43.8(2) ?
    C26 C21 C22 C23 . . . . 1.1(3) ?
    P1 C21 C22 C23 . . . . -176.75(18) ?
    C21 C22 C23 C24 . . . . -0.9(4) ?
    C22 C23 C24 C25 . . . . -0.2(4) ?
    C23 C24 C25 C26 . . . . 1.1(4) ?
    C22 C21 C26 C25 . . . . -0.2(3) ?
    P1 C21 C26 C25 . . . . 177.64(18) ?
    C24 C25 C26 C21 . . . . -0.9(4) ?
    C1 P1 C31 C32 . . . . 85.3(2) ?
    C21 P1 C31 C32 . . . . -148.4(2) ?
    C11 P1 C31 C32 . . . . -34.1(2) ?
    C1 P1 C31 C36 . . . . -94.8(2) ?
    C21 P1 C31 C36 . . . . 31.5(2) ?
    C11 P1 C31 C36 . . . . 145.8(2) ?
    C36 C31 C32 C33 . . . . 0.4(4) ?
    P1 C31 C32 C33 . . . . -179.7(2) ?
    C31 C32 C33 C34 . . . . -1.6(5) ?
    C32 C33 C34 C35 . . . . 1.2(5) ?
    C33 C34 C35 C36 . . . . 0.2(5) ?
    C34 C35 C36 C31 . . . . -1.3(4) ?
    C32 C31 C36 C35 . . . . 1.0(4) ?
    P1 C31 C36 C35 . . . . -178.9(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    P1 . O1 . . . 2.953(2) .
    P1 . O4 . . . 2.809(2) .
    C5 H5C Cg3 . 0.96 2.93 3.663(4) 134
    C25 H25 O4 2_755 0.93 2.40 3.323(3) 172.3
data_IIa
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
methyl tert-butyl 2-(triphenylphosphoranyliden)malonate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C26 H27 O4 P'
_chemical_formula_sum     'C26 H27 O4 P'
_chemical_formula_iupac     'C26 H27 O4 P'
_chemical_formula_weight     434.45
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n '
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     9.8140(7)
_cell_length_b     15.889(2)
_cell_length_c     15.404(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.413(2)
_cell_angle_gamma     90.00
_cell_volume     2402.0(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     7347
_cell_measurement_theta_min     2.43
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     140(5)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.16
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.201
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     920
_exptl_absorpt_coefficient_mu     0.143
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     140(5)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19840
_diffrn_reflns_av_R_equivalents     0.0208
_diffrn_reflns_av_sigmaI/netI     0.0192
_diffrn_reflns_theta_min     1.84
_diffrn_reflns_theta_max     27.82
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.930
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     5292
_reflns_number_gt     4501
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0597
_refine_ls_R_factor_gt     0.0516
_refine_ls_wR_factor_gt     0.1358
_refine_ls_wR_factor_ref     0.1444
_refine_ls_goodness_of_fit_ref     1.036
_refine_ls_restrained_S_all     1.036
_refine_ls_number_reflns     5292
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0764P)²+0.8536P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.008
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.595
_refine_diff_density_min     -0.453
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART-NT (Bruker, 2001)'
_computing_cell_refinement     'SAINT-NT (Bruker, 2001)'
_computing_data_reduction     'SAINT-NT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL-NT (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL-NT (Sheldrick, 2008) and PLATON (Spek, 2003)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    P P1 0.14127(4) 0.18082(3) 0.47388(3) 0.03449(14) Uani d . 1 . .
    O O1 -0.03175(14) 0.28668(8) 0.56513(8) 0.0484(3) Uani d . 1 . .
    O O2 -0.04149(14) 0.22305(9) 0.69524(8) 0.0525(3) Uani d . 1 . .
    O O3 0.11969(15) 0.08631(9) 0.70944(8) 0.0583(4) Uani d . 1 . .
    O O4 0.2686(2) 0.06909(18) 0.60761(12) 0.1345(12) Uani d . 1 . .
    C C1 0.09323(16) 0.16494(10) 0.58150(10) 0.0365(3) Uani d . 1 . .
    C C2 0.00120(17) 0.22425(10) 0.62166(10) 0.0392(4) Uani d . 1 . .
    C C3 0.16718(18) 0.10306(12) 0.63060(11) 0.0464(4) Uani d . 1 . .
    C C4 -0.1236(3) 0.35562(14) 0.58826(14) 0.0665(6) Uani d . 1 . .
    C C5 -0.1376(4) 0.40236(18) 0.50279(19) 0.0982(10) Uani d . 1 . .
    H H5A -0.0491 0.4191 0.4831 0.147 Uiso calc R 1 . .
    H H5B -0.1933 0.4514 0.5109 0.147 Uiso calc R 1 . .
    H H5C -0.1795 0.3662 0.4604 0.147 Uiso calc R 1 . .
    C C6 -0.0546(5) 0.40994(18) 0.6566(2) 0.1148(13) Uani d . 1 . .
    H H6A -0.0497 0.3796 0.7104 0.172 Uiso calc R 1 . .
    H H6B -0.1063 0.4606 0.6646 0.172 Uiso calc R 1 . .
    H H6C 0.0357 0.4240 0.6380 0.172 Uiso calc R 1 . .
    C C7 -0.2604(3) 0.3214(2) 0.6159(2) 0.1119(13) Uani d . 1 . .
    H H7A -0.2498 0.2907 0.6692 0.168 Uiso calc R 1 . .
    H H7B -0.2955 0.2846 0.5717 0.168 Uiso calc R 1 . .
    H H7C -0.3226 0.3672 0.6245 0.168 Uiso calc R 1 . .
    C C8 0.1943(3) 0.02723(16) 0.76090(15) 0.0767(7) Uani d . 1 . .
    H H8A 0.1602 0.0277 0.8192 0.115 Uiso calc R 1 . .
    H H8B 0.2890 0.0423 0.7615 0.115 Uiso calc R 1 . .
    H H8C 0.1839 -0.0281 0.7367 0.115 Uiso calc R 1 . .
    C C11 0.26076(17) 0.26686(10) 0.46337(11) 0.0387(4) Uani d . 1 . .
    C C12 0.3300(2) 0.28250(12) 0.38661(11) 0.0477(4) Uani d . 1 . .
    H H12A 0.3128 0.2493 0.3380 0.057 Uiso calc R 1 . .
    C C13 0.4241(2) 0.34692(14) 0.38185(14) 0.0588(5) Uani d . 1 . .
    H H13 0.4692 0.3575 0.3301 0.071 Uiso calc R 1 . .
    C C14 0.4506(3) 0.39522(15) 0.45370(16) 0.0708(7) Uani d . 1 . .
    H H14 0.5143 0.4384 0.4506 0.085 Uiso calc R 1 . .
    C C15 0.3836(3) 0.38024(15) 0.53036(15) 0.0707(7) Uani d . 1 . .
    H H15 0.4021 0.4134 0.5788 0.085 Uiso calc R 1 . .
    C C16 0.2890(2) 0.31607(12) 0.53573(12) 0.0512(5) Uani d . 1 . .
    H H16 0.2444 0.3059 0.5877 0.061 Uiso calc R 1 . .
    C C21 0.22434(17) 0.09091(10) 0.42527(10) 0.0387(4) Uani d . 1 . .
    C C22 0.1478(2) 0.03033(12) 0.38286(13) 0.0517(4) Uani d . 1 . .
    H H22 0.0537 0.0360 0.3789 0.062 Uiso calc R 1 . .
    C C23 0.2116(3) -0.03907(13) 0.34610(16) 0.0658(6) Uani d . 1 . .
    H H23 0.1600 -0.0800 0.3178 0.079 Uiso calc R 1 . .
    C C24 0.3503(3) -0.04726(14) 0.35148(16) 0.0666(6) Uani d . 1 . .
    H H24 0.3925 -0.0938 0.3268 0.080 Uiso calc R 1 . .
    C C25 0.4274(2) 0.01279(14) 0.39303(14) 0.0602(5) Uani d . 1 . .
    H H25 0.5216 0.0069 0.3962 0.072 Uiso calc R 1 . .
    C C26 0.36547(19) 0.08184(13) 0.43009(13) 0.0500(4) Uani d . 1 . .
    H H26 0.4179 0.1224 0.4583 0.060 Uiso calc R 1 . .
    C C31 -0.00707(18) 0.20010(11) 0.40597(11) 0.0418(4) Uani d . 1 . .
    C C32 -0.1290(2) 0.16113(13) 0.42658(14) 0.0539(5) Uani d . 1 . .
    H H32 -0.1345 0.1261 0.4748 0.065 Uiso calc R 1 . .
    C C33 -0.2431(2) 0.17488(16) 0.37440(17) 0.0695(6) Uani d . 1 . .
    H H33 -0.3251 0.1489 0.3882 0.083 Uiso calc R 1 . .
    C C34 -0.2367(3) 0.22568(18) 0.30367(17) 0.0772(7) Uani d . 1 . .
    H H34 -0.3143 0.2351 0.2700 0.093 Uiso calc R 1 . .
    C C35 -0.1165(3) 0.26294(19) 0.28190(16) 0.0804(8) Uani d . 1 . .
    H H35 -0.1117 0.2965 0.2326 0.096 Uiso calc R 1 . .
    C C36 -0.0010(2) 0.25077(15) 0.33332(14) 0.0625(5) Uani d . 1 . .
    H H36 0.0805 0.2769 0.3187 0.075 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    P1 C1 . 1.7451(16) y
    P1 C11 . 1.8092(17) ?
    P1 C21 . 1.8097(17) ?
    P1 C31 . 1.8126(17) ?
    O1 C2 . 1.357(2) ?
    O1 C4 . 1.464(2) ?
    O2 C2 . 1.211(2) y
    O3 C3 . 1.331(2) ?
    O3 C8 . 1.427(2) ?
    O4 C3 . 1.188(2) y
    C1 C3 . 1.434(2) y
    C1 C2 . 1.447(2) y
    C4 C7 . 1.512(4) ?
    C4 C6 . 1.516(4) ?
    C4 C5 . 1.517(3) ?
    C5 H5A . 0.9600 ?
    C5 H5B . 0.9600 ?
    C5 H5C . 0.9600 ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C11 C16 . 1.388(2) ?
    C11 C12 . 1.390(2) ?
    C12 C13 . 1.381(3) ?
    C12 H12A . 0.9300 ?
    C13 C14 . 1.370(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.376(3) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.382(3) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C21 C22 . 1.382(2) ?
    C21 C26 . 1.394(2) ?
    C22 C23 . 1.390(3) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.369(3) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.373(3) ?
    C24 H24 . 0.9300 ?
    C25 C26 . 1.380(3) ?
    C25 H25 . 0.9300 ?
    C26 H26 . 0.9300 ?
    C31 C36 . 1.380(3) ?
    C31 C32 . 1.386(3) ?
    C32 C33 . 1.391(3) ?
    C32 H32 . 0.9300 ?
    C33 C34 . 1.358(4) ?
    C33 H33 . 0.9300 ?
    C34 C35 . 1.364(4) ?
    C34 H34 . 0.9300 ?
    C35 C36 . 1.392(3) ?
    C35 H35 . 0.9300 ?
    C36 H36 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 P1 C11 . . 111.96(8) ?
    C1 P1 C21 . . 113.86(8) ?
    C11 P1 C21 . . 105.38(8) ?
    C1 P1 C31 . . 110.57(8) ?
    C11 P1 C31 . . 109.82(8) ?
    C21 P1 C31 . . 104.89(8) ?
    C2 O1 C4 . . 122.33(14) ?
    C3 O3 C8 . . 117.18(16) ?
    C3 C1 C2 . . 122.41(15) ?
    C3 C1 P1 . . 117.44(12) ?
    C2 C1 P1 . . 119.05(12) ?
    O2 C2 O1 . . 121.96(15) ?
    O2 C2 C1 . . 127.64(15) ?
    O1 C2 C1 . . 110.37(14) ?
    O4 C3 O3 . . 118.73(17) ?
    O4 C3 C1 . . 125.16(17) ?
    O3 C3 C1 . . 116.04(15) ?
    O1 C4 C7 . . 110.4(2) ?
    O1 C4 C6 . . 108.8(2) ?
    C7 C4 C6 . . 113.7(3) ?
    O1 C4 C5 . . 101.97(18) ?
    C7 C4 C5 . . 110.2(2) ?
    C6 C4 C5 . . 111.2(2) ?
    C4 C5 H5A . . 109.5 ?
    C4 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    C4 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    C4 C6 H6A . . 109.5 ?
    C4 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C4 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    C4 C7 H7A . . 109.5 ?
    C4 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C4 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    O3 C8 H8A . . 109.5 ?
    O3 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    O3 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C16 C11 C12 . . 119.09(16) ?
    C16 C11 P1 . . 118.67(13) ?
    C12 C11 P1 . . 122.16(13) ?
    C13 C12 C11 . . 120.58(17) ?
    C13 C12 H12A . . 119.7 ?
    C11 C12 H12A . . 119.7 ?
    C14 C13 C12 . . 119.70(18) ?
    C14 C13 H13 . . 120.1 ?
    C12 C13 H13 . . 120.1 ?
    C13 C14 C15 . . 120.47(19) ?
    C13 C14 H14 . . 119.8 ?
    C15 C14 H14 . . 119.8 ?
    C14 C15 C16 . . 120.27(19) ?
    C14 C15 H15 . . 119.9 ?
    C16 C15 H15 . . 119.9 ?
    C15 C16 C11 . . 119.88(17) ?
    C15 C16 H16 . . 120.1 ?
    C11 C16 H16 . . 120.1 ?
    C22 C21 C26 . . 119.29(16) ?
    C22 C21 P1 . . 120.04(14) ?
    C26 C21 P1 . . 120.66(14) ?
    C21 C22 C23 . . 120.03(19) ?
    C21 C22 H22 . . 120.0 ?
    C23 C22 H22 . . 120.0 ?
    C24 C23 C22 . . 120.1(2) ?
    C24 C23 H23 . . 120.0 ?
    C22 C23 H23 . . 120.0 ?
    C23 C24 C25 . . 120.43(19) ?
    C23 C24 H24 . . 119.8 ?
    C25 C24 H24 . . 119.8 ?
    C24 C25 C26 . . 120.1(2) ?
    C24 C25 H25 . . 119.9 ?
    C26 C25 H25 . . 119.9 ?
    C25 C26 C21 . . 120.04(19) ?
    C25 C26 H26 . . 120.0 ?
    C21 C26 H26 . . 120.0 ?
    C36 C31 C32 . . 119.25(18) ?
    C36 C31 P1 . . 121.82(15) ?
    C32 C31 P1 . . 118.91(14) ?
    C31 C32 C33 . . 119.4(2) ?
    C31 C32 H32 . . 120.3 ?
    C33 C32 H32 . . 120.3 ?
    C34 C33 C32 . . 121.0(2) ?
    C34 C33 H33 . . 119.5 ?
    C32 C33 H33 . . 119.5 ?
    C33 C34 C35 . . 120.1(2) ?
    C33 C34 H34 . . 120.0 ?
    C35 C34 H34 . . 120.0 ?
    C34 C35 C36 . . 120.1(2) ?
    C34 C35 H35 . . 119.9 ?
    C36 C35 H35 . . 119.9 ?
    C31 C36 C35 . . 120.2(2) ?
    C31 C36 H36 . . 119.9 ?
    C35 C36 H36 . . 119.9 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C11 P1 C1 C3 . . . . -94.67(15) ?
    C21 P1 C1 C3 . . . . 24.74(16) ?
    C31 P1 C1 C3 . . . . 142.52(14) ?
    C11 P1 C1 C2 . . . . 73.63(15) ?
    C21 P1 C1 C2 . . . . -166.96(13) ?
    C31 P1 C1 C2 . . . . -49.18(15) ?
    C4 O1 C2 O2 . . . . -1.5(3) ?
    C4 O1 C2 C1 . . . . 179.97(17) ?
    C3 C1 C2 O2 . . . . -11.8(3) ?
    P1 C1 C2 O2 . . . . -179.49(15) ?
    C3 C1 C2 O1 . . . . 166.58(16) ?
    P1 C1 C2 O1 . . . . -1.12(19) ?
    C8 O3 C3 O4 . . . . -0.7(3) ?
    C8 O3 C3 C1 . . . . -177.8(2) ?
    C2 C1 C3 O4 . . . . -158.2(3) ?
    P1 C1 C3 O4 . . . . 9.6(3) ?
    C2 C1 C3 O3 . . . . 18.6(3) ?
    P1 C1 C3 O3 . . . . -173.51(14) ?
    C2 O1 C4 C7 . . . . -57.8(3) ?
    C2 O1 C4 C6 . . . . 67.6(3) ?
    C2 O1 C4 C5 . . . . -174.9(2) ?
    C1 P1 C11 C16 . . . . -7.33(18) ?
    C21 P1 C11 C16 . . . . -131.61(15) ?
    C31 P1 C11 C16 . . . . 115.91(16) ?
    C1 P1 C11 C12 . . . . 169.37(15) ?
    C21 P1 C11 C12 . . . . 45.09(17) ?
    C31 P1 C11 C12 . . . . -67.39(17) ?
    C16 C11 C12 C13 . . . . -1.0(3) ?
    P1 C11 C12 C13 . . . . -177.70(17) ?
    C11 C12 C13 C14 . . . . 0.8(4) ?
    C12 C13 C14 C15 . . . . -0.3(4) ?
    C13 C14 C15 C16 . . . . 0.2(4) ?
    C14 C15 C16 C11 . . . . -0.4(4) ?
    C12 C11 C16 C15 . . . . 0.8(3) ?
    P1 C11 C16 C15 . . . . 177.62(19) ?
    C1 P1 C21 C22 . . . . 89.73(16) ?
    C11 P1 C21 C22 . . . . -147.19(15) ?
    C31 P1 C21 C22 . . . . -31.27(17) ?
    C1 P1 C21 C26 . . . . -90.24(16) ?
    C11 P1 C21 C26 . . . . 32.84(16) ?
    C31 P1 C21 C26 . . . . 148.75(15) ?
    C26 C21 C22 C23 . . . . 0.5(3) ?
    P1 C21 C22 C23 . . . . -179.50(16) ?
    C21 C22 C23 C24 . . . . -0.3(3) ?
    C22 C23 C24 C25 . . . . 0.0(4) ?
    C23 C24 C25 C26 . . . . 0.3(4) ?
    C24 C25 C26 C21 . . . . -0.1(3) ?
    C22 C21 C26 C25 . . . . -0.2(3) ?
    P1 C21 C26 C25 . . . . 179.73(15) ?
    C1 P1 C31 C36 . . . . 149.13(17) ?
    C11 P1 C31 C36 . . . . 25.08(19) ?
    C21 P1 C31 C36 . . . . -87.72(18) ?
    C1 P1 C31 C32 . . . . -32.46(18) ?
    C11 P1 C31 C32 . . . . -156.51(15) ?
    C21 P1 C31 C32 . . . . 90.70(16) ?
    C36 C31 C32 C33 . . . . -0.9(3) ?
    P1 C31 C32 C33 . . . . -179.39(16) ?
    C31 C32 C33 C34 . . . . 0.1(3) ?
    C32 C33 C34 C35 . . . . 1.2(4) ?
    C33 C34 C35 C36 . . . . -1.7(4) ?
    C32 C31 C36 C35 . . . . 0.5(3) ?
    P1 C31 C36 C35 . . . . 178.9(2) ?
    C34 C35 C36 C31 . . . . 0.8(4) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    P1 . O1 . . . 2.729(2) .
    P1 . O4 . . . 2.986(2) .
    C5 H5C Cg3 . 0.96 2.99 3.788(3) 141
    C23 H23 O2 3_556 0.93 2.56 3.424(2) 154
    C25 H25 O4 3_656 0.93 2.39 3.255(3) 155
    C34 H34 O2 4_565 0.93 2.59 3.511(3) 171
    C13 H13 O3 4_665 0.93 2.54 3.455(3) 166
data_IIb
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
ethyl tert-butyl 2-(triphenylphosphoranyliden)malonate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C27 H29 O4 P'
_chemical_formula_sum     'C27 H29 O4 P'
_chemical_formula_iupac     'C27 H29 O4 P'
_chemical_formula_weight     448.47
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.9616(7)
_cell_length_b     10.3589(8)
_cell_length_c     14.5644(11)
_cell_angle_alpha     97.388(2)
_cell_angle_beta     107.705(3)
_cell_angle_gamma     105.338(2)
_cell_volume     1209.55(16)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2361
_cell_measurement_theta_min     2.28
_cell_measurement_theta_max     23.79
_cell_measurement_temperature     140(5)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.231
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     476
_exptl_absorpt_coefficient_mu     0.144
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     140(5)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10154
_diffrn_reflns_av_R_equivalents     0.0193
_diffrn_reflns_av_sigmaI/netI     0.0360
_diffrn_reflns_theta_min     2.09
_diffrn_reflns_theta_max     27.88
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.897
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     5183
_reflns_number_gt     3919
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0672
_refine_ls_R_factor_gt     0.0502
_refine_ls_wR_factor_gt     0.1251
_refine_ls_wR_factor_ref     0.1356
_refine_ls_goodness_of_fit_ref     1.026
_refine_ls_restrained_S_all     1.026
_refine_ls_number_reflns     5183
_refine_ls_number_parameters     299
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0700P)²+0.1417P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.018
_refine_ls_shift/su_mean     0.004
_refine_diff_density_max     0.355
_refine_diff_density_min     -0.157
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART-NT (Bruker, 2001)'
_computing_cell_refinement     'SAINT-NT (Bruker, 2001)'
_computing_data_reduction     'SAINT-NT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL-NT (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL-NT (Sheldrick, 2008) and PLATON (Spek, 2003)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    P P1 0.42921(4) 0.76990(4) 0.21270(3) 0.03683(9) Uani d . 1 . .
    O O1 0.61257(12) 0.58687(10) 0.27373(8) 0.0503(3) Uani d . 1 . .
    O O2 0.84030(12) 0.68548(12) 0.24039(9) 0.0627(3) Uani d . 1 . .
    O O3 0.89536(17) 0.95837(9) 0.25831(11) 0.0572(4) Uani d PD 0.747(4) A 1
    C C8 0.9971(3) 1.10238(17) 0.29425(10) 0.0817(7) Uani d PD 0.747(4) A 1
    H H8A 1.0887 1.1173 0.2703 0.098 Uiso calc PR 0.747(4) A 1
    H H8B 0.9315 1.1587 0.2671 0.098 Uiso calc PR 0.747(4) A 1
    C C9 1.0620(4) 1.1465(4) 0.40136(14) 0.0982(11) Uani d PD 0.747(4) A 1
    H H9A 1.1305 1.2410 0.4207 0.147 Uiso calc PR 0.747(4) A 1
    H H9B 1.1265 1.0908 0.4289 0.147 Uiso calc PR 0.747(4) A 1
    H H9C 0.9720 1.1367 0.4254 0.147 Uiso calc PR 0.747(4) A 1
    O O3' 0.8921(5) 0.97469(16) 0.2822(3) 0.0572(4) Uani d PD 0.253(4) A 2
    C C8' 1.0056(6) 1.1099(3) 0.2922(3) 0.0817(7) Uani d PD 0.253(4) A 2
    H H8'A 1.1063 1.1042 0.2825 0.098 Uiso calc PR 0.253(4) A 2
    H H8'B 0.9546 1.1598 0.2469 0.098 Uiso calc PR 0.253(4) A 2
    C C9' 1.0355(14) 1.1705(14) 0.3943(4) 0.0982(11) Uani d PD 0.253(4) A 2
    H H9'A 1.1079 1.2637 0.4118 0.147 Uiso calc PR 0.253(4) A 2
    H H9'B 1.0860 1.1186 0.4368 0.147 Uiso calc PR 0.253(4) A 2
    H H9'C 0.9324 1.1695 0.4017 0.147 Uiso calc PR 0.253(4) A 2
    O O4 0.67961(12) 1.03388(11) 0.26410(8) 0.0535(3) Uani d . 1 A .
    C C1 0.63747(16) 0.79704(14) 0.23226(10) 0.0389(3) Uani d . 1 A .
    C C2 0.71058(17) 0.68898(15) 0.24759(11) 0.0437(4) Uani d . 1 . .
    C C3 0.73341(17) 0.93876(16) 0.25398(11) 0.0434(4) Uani d . 1 . .
    C C4 0.6506(2) 0.45896(17) 0.28767(14) 0.0604(5) Uani d . 1 . .
    C C5 0.5013(3) 0.3781(2) 0.30767(18) 0.0906(7) Uani d . 1 . .
    H H5A 0.4969 0.4265 0.3671 0.136 Uiso calc R 1 . .
    H H5B 0.5095 0.2894 0.3156 0.136 Uiso calc R 1 . .
    H H5C 0.4027 0.3670 0.2531 0.136 Uiso calc R 1 . .
    C C6 0.6591(3) 0.3845(2) 0.19436(17) 0.0876(7) Uani d . 1 . .
    H H6A 0.7545 0.4366 0.1825 0.131 Uiso calc R 1 . .
    H H6B 0.5610 0.3740 0.1395 0.131 Uiso calc R 1 . .
    H H6C 0.6671 0.2955 0.2016 0.131 Uiso calc R 1 . .
    C C7 0.8083(3) 0.4914(2) 0.37591(19) 0.1079(9) Uani d D 1 . .
    H H7A 0.7975 0.5395 0.4332 0.162 Uiso calc R 1 . .
    H H7B 0.8995 0.5478 0.3624 0.162 Uiso calc R 1 . .
    H H7C 0.8280 0.4074 0.3880 0.162 Uiso calc R 1 . .
    C C11 0.38572(16) 0.79984(15) 0.32493(10) 0.0408(4) Uani d . 1 . .
    C C12 0.23174(17) 0.80506(16) 0.32664(12) 0.0484(4) Uani d . 1 . .
    H H12 0.1475 0.7972 0.2679 0.058 Uiso calc R 1 . .
    C C13 0.2051(2) 0.82173(17) 0.41457(12) 0.0557(4) Uani d . 1 . .
    H H13 0.1027 0.8250 0.4152 0.067 Uiso calc R 1 . .
    C C14 0.3288(2) 0.83371(18) 0.50179(13) 0.0601(5) Uani d . 1 . .
    H H14 0.3101 0.8453 0.5613 0.072 Uiso calc R 1 . .
    C C15 0.4802(2) 0.82852(19) 0.50116(12) 0.0600(5) Uani d . 1 . .
    H H15 0.5637 0.8365 0.5603 0.072 Uiso calc R 1 . .
    C C16 0.50869(18) 0.81148(16) 0.41330(11) 0.0479(4) Uani d . 1 . .
    H H16 0.6113 0.8078 0.4134 0.058 Uiso calc R 1 . .
    C C21 0.35241(16) 0.87693(14) 0.13323(10) 0.0387(3) Uani d . 1 . .
    C C22 0.35132(18) 0.85366(16) 0.03733(11) 0.0482(4) Uani d . 1 . .
    H H22 0.3908 0.7853 0.0161 0.058 Uiso calc R 1 . .
    C C23 0.2925(2) 0.93023(17) -0.02746(12) 0.0541(4) Uani d . 1 . .
    H H23 0.2928 0.9135 -0.0917 0.065 Uiso calc R 1 . .
    C C24 0.2337(2) 1.03107(17) 0.00327(13) 0.0584(5) Uani d . 1 . .
    H H24 0.1929 1.0823 -0.0403 0.070 Uiso calc R 1 . .
    C C25 0.2354(2) 1.05596(18) 0.09807(14) 0.0659(5) Uani d . 1 . .
    H H25 0.1954 1.1243 0.1187 0.079 Uiso calc R 1 . .
    C C26 0.2958(2) 0.98094(17) 0.16349(12) 0.0549(4) Uani d . 1 . .
    H H26 0.2984 1.0003 0.2282 0.066 Uiso calc R 1 . .
    C C31 0.30318(16) 0.59683(14) 0.14338(11) 0.0408(4) Uani d . 1 . .
    C C32 0.16589(19) 0.52632(17) 0.16322(13) 0.0542(4) Uani d . 1 . .
    H H32 0.1432 0.5649 0.2166 0.065 Uiso calc R 1 . .
    C C33 0.0628(2) 0.39923(18) 0.10418(15) 0.0628(5) Uani d . 1 . .
    H H33 -0.0288 0.3526 0.1182 0.075 Uiso calc R 1 . .
    C C34 0.0946(2) 0.34161(17) 0.02529(14) 0.0603(5) Uani d . 1 . .
    H H34 0.0238 0.2567 -0.0149 0.072 Uiso calc R 1 . .
    C C35 0.2306(2) 0.40903(17) 0.00554(13) 0.0578(5) Uani d . 1 . .
    H H35 0.2525 0.3693 -0.0478 0.069 Uiso calc R 1 . .
    C C36 0.33556(19) 0.53558(16) 0.06426(11) 0.0491(4) Uani d . 1 . .
    H H36 0.4285 0.5801 0.0508 0.059 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    P1 C1 . 1.7383(14) y
    P1 C11 . 1.8004(15) ?
    P1 C31 . 1.8107(14) ?
    P1 C21 . 1.8142(15) ?
    O1 C2 . 1.3603(18) ?
    O1 C4 . 1.476(2) ?
    O2 C2 . 1.2080(18) y
    O3 C3 . 1.392(2) ?
    O3 C8 . 1.4560(17) ?
    C8 C9 . 1.451(2) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    O3' C3 . 1.287(4) ?
    O3' C8' . 1.4560(19) ?
    C8' C9' . 1.451(2) ?
    C8' H8'A . 0.9700 ?
    C8' H8'B . 0.9700 ?
    C9' H9'A . 0.9600 ?
    C9' H9'B . 0.9600 ?
    C9' H9'C . 0.9600 ?
    O4 C3 . 1.2174(19) y
    C1 C3 . 1.429(2) y
    C1 C2 . 1.448(2) y
    C4 C6 . 1.507(3) ?
    C4 C5 . 1.511(3) ?
    C4 C7 . 1.515(3) ?
    C5 H5A . 0.9600 ?
    C5 H5B . 0.9600 ?
    C5 H5C . 0.9600 ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C11 C16 . 1.383(2) ?
    C11 C12 . 1.403(2) ?
    C12 C13 . 1.370(2) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.374(2) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.374(2) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.378(2) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C21 C22 . 1.383(2) ?
    C21 C26 . 1.384(2) ?
    C22 C23 . 1.381(2) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.373(2) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.366(3) ?
    C24 H24 . 0.9300 ?
    C25 C26 . 1.380(2) ?
    C25 H25 . 0.9300 ?
    C26 H26 . 0.9300 ?
    C31 C32 . 1.388(2) ?
    C31 C36 . 1.388(2) ?
    C32 C33 . 1.381(2) ?
    C32 H32 . 0.9300 ?
    C33 C34 . 1.368(3) ?
    C33 H33 . 0.9300 ?
    C34 C35 . 1.368(2) ?
    C34 H34 . 0.9300 ?
    C35 C36 . 1.380(2) ?
    C35 H35 . 0.9300 ?
    C36 H36 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 P1 C11 . . 113.80(6) ?
    C1 P1 C31 . . 111.58(7) ?
    C11 P1 C31 . . 107.85(7) ?
    C1 P1 C21 . . 110.05(7) ?
    C11 P1 C21 . . 109.51(7) ?
    C31 P1 C21 . . 103.53(6) ?
    C2 O1 C4 . . 122.35(13) ?
    C3 O3 C8 . . 112.12(16) ?
    C9 C8 O3 . . 113.2(2) ?
    C9 C8 H8A . . 108.9 ?
    O3 C8 H8A . . 108.9 ?
    C9 C8 H8B . . 108.9 ?
    O3 C8 H8B . . 108.9 ?
    H8A C8 H8B . . 107.7 ?
    C8 C9 H9A . . 109.5 ?
    C8 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C8 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C3 O3' C8' . . 127.1(3) ?
    C9' C8' O3' . . 99.5(6) ?
    C9' C8' H8'A . . 111.9 ?
    O3' C8' H8'A . . 111.9 ?
    C9' C8' H8'B . . 111.8 ?
    O3' C8' H8'B . . 111.9 ?
    H8'A C8' H8'B . . 109.6 ?
    C8' C9' H9'A . . 109.5 ?
    C8' C9' H9'B . . 109.5 ?
    H9'A C9' H9'B . . 109.5 ?
    C8' C9' H9'C . . 109.5 ?
    H9'A C9' H9'C . . 109.5 ?
    H9'B C9' H9'C . . 109.5 ?
    C3 C1 C2 . . 123.02(12) ?
    C3 C1 P1 . . 113.73(11) ?
    C2 C1 P1 . . 121.77(10) ?
    O2 C2 O1 . . 122.42(15) ?
    O2 C2 C1 . . 127.20(15) ?
    O1 C2 C1 . . 110.38(12) ?
    O4 C3 O3' . . 114.29(16) ?
    O4 C3 O3 . . 122.50(13) ?
    O4 C3 C1 . . 124.35(13) ?
    O3' C3 C1 . . 120.22(15) ?
    O3 C3 C1 . . 113.09(13) ?
    O1 C4 C6 . . 110.87(15) ?
    O1 C4 C5 . . 101.49(15) ?
    C6 C4 C5 . . 110.16(16) ?
    O1 C4 C7 . . 109.66(14) ?
    C6 C4 C7 . . 112.54(19) ?
    C5 C4 C7 . . 111.59(18) ?
    C4 C5 H5A . . 109.5 ?
    C4 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    C4 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    C4 C6 H6A . . 109.5 ?
    C4 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C4 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    C4 C7 H7A . . 109.5 ?
    C4 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C4 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    C16 C11 C12 . . 118.70(14) ?
    C16 C11 P1 . . 117.81(12) ?
    C12 C11 P1 . . 123.41(11) ?
    C13 C12 C11 . . 120.20(14) ?
    C13 C12 H12 . . 119.9 ?
    C11 C12 H12 . . 119.9 ?
    C12 C13 C14 . . 120.39(16) ?
    C12 C13 H13 . . 119.8 ?
    C14 C13 H13 . . 119.8 ?
    C13 C14 C15 . . 120.02(16) ?
    C13 C14 H14 . . 120.0 ?
    C15 C14 H14 . . 120.0 ?
    C14 C15 C16 . . 120.26(15) ?
    C14 C15 H15 . . 119.9 ?
    C16 C15 H15 . . 119.9 ?
    C15 C16 C11 . . 120.44(15) ?
    C15 C16 H16 . . 119.8 ?
    C11 C16 H16 . . 119.8 ?
    C22 C21 C26 . . 118.28(14) ?
    C22 C21 P1 . . 118.11(12) ?
    C26 C21 P1 . . 123.61(12) ?
    C23 C22 C21 . . 121.10(16) ?
    C23 C22 H22 . . 119.4 ?
    C21 C22 H22 . . 119.5 ?
    C24 C23 C22 . . 119.78(16) ?
    C24 C23 H23 . . 120.1 ?
    C22 C23 H23 . . 120.1 ?
    C25 C24 C23 . . 119.73(16) ?
    C25 C24 H24 . . 120.1 ?
    C23 C24 H24 . . 120.1 ?
    C24 C25 C26 . . 120.77(17) ?
    C24 C25 H25 . . 119.6 ?
    C26 C25 H25 . . 119.6 ?
    C25 C26 C21 . . 120.31(16) ?
    C25 C26 H26 . . 119.8 ?
    C21 C26 H26 . . 119.8 ?
    C32 C31 C36 . . 118.47(13) ?
    C32 C31 P1 . . 121.13(12) ?
    C36 C31 P1 . . 120.25(11) ?
    C33 C32 C31 . . 120.42(17) ?
    C33 C32 H32 . . 119.8 ?
    C31 C32 H32 . . 119.8 ?
    C34 C33 C32 . . 120.36(16) ?
    C34 C33 H33 . . 119.8 ?
    C32 C33 H33 . . 119.8 ?
    C33 C34 C35 . . 119.91(15) ?
    C33 C34 H34 . . 120.0 ?
    C35 C34 H34 . . 120.0 ?
    C34 C35 C36 . . 120.46(17) ?
    C34 C35 H35 . . 119.8 ?
    C36 C35 H35 . . 119.8 ?
    C35 C36 C31 . . 120.36(15) ?
    C35 C36 H36 . . 119.8 ?
    C31 C36 H36 . . 119.8 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C3 O3 C8 C9 . . . . 82.8(3) ?
    C3 O3' C8' C9' . . . . 89.8(7) ?
    C11 P1 C1 C3 . . . . -78.64(12) ?
    C31 P1 C1 C3 . . . . 159.04(11) ?
    C21 P1 C1 C3 . . . . 44.70(13) ?
    C11 P1 C1 C2 . . . . 87.90(13) ?
    C31 P1 C1 C2 . . . . -34.42(14) ?
    C21 P1 C1 C2 . . . . -148.77(12) ?
    C4 O1 C2 O2 . . . . -4.9(2) ?
    C4 O1 C2 C1 . . . . 175.87(12) ?
    C3 C1 C2 O2 . . . . -32.2(2) ?
    P1 C1 C2 O2 . . . . 162.53(13) ?
    C3 C1 C2 O1 . . . . 146.98(14) ?
    P1 C1 C2 O1 . . . . -18.30(17) ?
    C8' O3' C3 O4 . . . . -22.0(5) ?
    C8' O3' C3 O3 . . . . 103.0(5) ?
    C8' O3' C3 C1 . . . . 169.7(3) ?
    C8 O3 C3 O4 . . . . 10.9(2) ?
    C8 O3 C3 O3' . . . . -51.4(2) ?
    C8 O3 C3 C1 . . . . -171.79(13) ?
    C2 C1 C3 O4 . . . . -162.15(15) ?
    P1 C1 C3 O4 . . . . 4.2(2) ?
    C2 C1 C3 O3' . . . . 4.9(3) ?
    P1 C1 C3 O3' . . . . 171.3(2) ?
    C2 C1 C3 O3 . . . . 20.5(2) ?
    P1 C1 C3 O3 . . . . -173.11(11) ?
    C2 O1 C4 C6 . . . . -58.90(18) ?
    C2 O1 C4 C5 . . . . -175.89(14) ?
    C2 O1 C4 C7 . . . . 66.0(2) ?
    C1 P1 C11 C16 . . . . -13.50(15) ?
    C31 P1 C11 C16 . . . . 110.86(12) ?
    C21 P1 C11 C16 . . . . -137.12(12) ?
    C1 P1 C11 C12 . . . . 169.76(12) ?
    C31 P1 C11 C12 . . . . -65.88(14) ?
    C21 P1 C11 C12 . . . . 46.14(14) ?
    C16 C11 C12 C13 . . . . 0.2(2) ?
    P1 C11 C12 C13 . . . . 176.87(12) ?
    C11 C12 C13 C14 . . . . 0.1(2) ?
    C12 C13 C14 C15 . . . . -0.2(3) ?
    C13 C14 C15 C16 . . . . 0.1(3) ?
    C14 C15 C16 C11 . . . . 0.2(3) ?
    C12 C11 C16 C15 . . . . -0.3(2) ?
    P1 C11 C16 C15 . . . . -177.20(13) ?
    C1 P1 C21 C22 . . . . 63.88(12) ?
    C11 P1 C21 C22 . . . . -170.31(10) ?
    C31 P1 C21 C22 . . . . -55.49(12) ?
    C1 P1 C21 C26 . . . . -115.75(13) ?
    C11 P1 C21 C26 . . . . 10.05(14) ?
    C31 P1 C21 C26 . . . . 124.87(13) ?
    C26 C21 C22 C23 . . . . -1.2(2) ?
    P1 C21 C22 C23 . . . . 179.17(11) ?
    C21 C22 C23 C24 . . . . -0.1(2) ?
    C22 C23 C24 C25 . . . . 0.7(2) ?
    C23 C24 C25 C26 . . . . 0.1(3) ?
    C24 C25 C26 C21 . . . . -1.4(3) ?
    C22 C21 C26 C25 . . . . 1.9(2) ?
    P1 C21 C26 C25 . . . . -178.43(13) ?
    C1 P1 C31 C32 . . . . 143.80(13) ?
    C11 P1 C31 C32 . . . . 18.12(15) ?
    C21 P1 C31 C32 . . . . -97.89(14) ?
    C1 P1 C31 C36 . . . . -40.81(14) ?
    C11 P1 C31 C36 . . . . -166.49(12) ?
    C21 P1 C31 C36 . . . . 77.51(13) ?
    C36 C31 C32 C33 . . . . -1.1(2) ?
    P1 C31 C32 C33 . . . . 174.34(14) ?
    C31 C32 C33 C34 . . . . -0.2(3) ?
    C32 C33 C34 C35 . . . . 1.0(3) ?
    C33 C34 C35 C36 . . . . -0.5(3) ?
    C34 C35 C36 C31 . . . . -0.8(3) ?
    C32 C31 C36 C35 . . . . 1.6(2) ?
    P1 C31 C36 C35 . . . . -173.87(13) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    P1 . O1 . . . 2.877(2) .
    P1 . O4 . . . 2.877(2) .
    C5 H5C Cg3 . 0.96 3.07 3.944(2) 152
    C34 H34 Cg2 2_565 0.93 2.90 3.712(2) 146
    C12 H12 O2 1_455 0.93 2.57 3.168(2) 123
