#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/81/2018187.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2018187
loop_
_publ_author_name
'Castañeda, Fernando'
'Silva, Paul'
'Bunton, Clifford A.'
'Garland, María Teresa'
'Baggio, Ricardo'
_publ_section_title
;
 Conformations of diester triphenylphosphonium ylides with an ylidic
 ester or keto and ester ylidic groups
;
_journal_coeditor_code           GT3033
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o319
_journal_page_last               o323
_journal_paper_doi               10.1107/S0108270111027508
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C26 H27 O4 P'
_chemical_formula_moiety         'C26 H27 O4 P'
_chemical_formula_sum            'C26 H27 O4 P'
_chemical_formula_weight         434.45
_chemical_name_systematic
;
diethyl 2-(triphenylphosphoranylidene)succinate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.7357(10)
_cell_length_b                   16.8280(18)
_cell_length_c                   31.896(4)
_cell_measurement_reflns_used    982
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      50.12
_cell_measurement_theta_min      4.23
_cell_volume                     4688.9(9)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker SMART? CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0856
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            36723
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0767P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1386
_reflns_number_gt                3279
_reflns_number_total             5370
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gt3033.cif
_cod_data_source_block           III
_cod_database_code               2018187
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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_symmetry_multiplicity
P P1 0.38078(5) 0.69916(3) 0.386546(14) 0.03634(15) Uani d . 1 1
C C1 0.4447(2) 0.79581(10) 0.38635(5) 0.0408(4) Uani d . 1 1
C C2 0.3418(2) 0.85878(11) 0.39276(6) 0.0448(5) Uani d . 1 1
C C4 0.0842(3) 0.89068(13) 0.41259(7) 0.0634(6) Uani d . 1 1
H H4E -0.0206 0.8718 0.4062 0.076 Uiso calc R 1 1
H H4D 0.0996 0.9419 0.3979 0.076 Uiso calc R 1 1
C C5 0.0989(3) 0.90361(17) 0.45882(8) 0.0937(9) Uani d . 1 1
H H5F 0.0228 0.9427 0.4680 0.141 Uiso calc R 1 1
H H5D 0.2019 0.9233 0.4652 0.141 Uiso calc R 1 1
H H5E 0.0817 0.8533 0.4735 0.141 Uiso calc R 1 1
C C7 0.6443(2) 0.84084(12) 0.33282(6) 0.0486(5) Uani d . 1 1
C C8 0.8441(3) 0.88952(18) 0.28885(7) 0.0786(8) Uani d . 1 1
H H8A 0.7728 0.9290 0.2767 0.094 Uiso calc R 1 1
H H8B 0.8510 0.8437 0.2695 0.094 Uiso calc R 1 1
C C9 0.9968(3) 0.92536(15) 0.29493(7) 0.0758(7) Uani d . 1 1
H H9A 1.0368 0.9435 0.2679 0.114 Uiso calc R 1 1
H H9B 1.0665 0.8857 0.3068 0.114 Uiso calc R 1 1
H H9C 0.9886 0.9707 0.3141 0.114 Uiso calc R 1 1
C C10 0.6092(2) 0.81764(11) 0.37734(6) 0.0442(5) Uani d . 1 1
H H10A 0.6381 0.8624 0.3959 0.053 Uiso calc R 1 1
H H10B 0.6747 0.7718 0.3849 0.053 Uiso calc R 1 1
O O1 0.19299(15) 0.83379(8) 0.39720(4) 0.0532(4) Uani d . 1 1
O O2 0.37471(17) 0.92975(8) 0.39475(5) 0.0646(4) Uani d . 1 1
O O5 0.55822(19) 0.84003(12) 0.30378(5) 0.0841(5) Uani d . 1 1
O O6 0.78997(16) 0.86372(9) 0.32963(4) 0.0647(4) Uani d . 1 1
C C1A 0.2689(2) 0.66724(11) 0.34156(5) 0.0394(4) Uani d . 1 1
C C2A 0.2356(2) 0.58718(11) 0.33495(6) 0.0494(5) Uani d . 1 1
H H2A 0.2702 0.5487 0.3545 0.059 Uiso calc R 1 1
C C3A 0.1535(3) 0.56328(13) 0.30046(6) 0.0583(6) Uani d . 1 1
H H3A 0.1305 0.5086 0.2964 0.070 Uiso calc R 1 1
C C4A 0.1043(3) 0.61895(15) 0.27166(7) 0.0674(6) Uani d . 1 1
H H4A 0.0469 0.6027 0.2479 0.081 Uiso calc R 1 1
C C5A 0.1384(3) 0.69795(14) 0.27739(7) 0.0716(7) Uani d . 1 1
H H5A 0.1049 0.7361 0.2575 0.086 Uiso calc R 1 1
C C6A 0.2215(3) 0.72220(12) 0.31208(6) 0.0578(6) Uani d . 1 1
H H6A 0.2460 0.7768 0.3156 0.069 Uiso calc R 1 1
C C1B 0.5467(2) 0.63510(10) 0.38504(6) 0.0426(4) Uani d . 1 1
C C2B 0.5955(2) 0.59260(13) 0.41934(7) 0.0619(6) Uani d . 1 1
H H2B 0.5397 0.5945 0.4449 0.074 Uiso calc R 1 1
C C3B 0.7286(3) 0.54631(14) 0.41617(10) 0.0831(8) Uani d . 1 1
H H3B 0.7617 0.5160 0.4396 0.100 Uiso calc R 1 1
C C4B 0.8107(3) 0.54424(14) 0.38006(11) 0.0811(8) Uani d . 1 1
H H4B 0.9014 0.5132 0.3785 0.097 Uiso calc R 1 1
C C5B 0.7631(3) 0.58684(15) 0.34599(9) 0.0778(7) Uani d . 1 1
H H5B 0.8214 0.5859 0.3209 0.093 Uiso calc R 1 1
C C6B 0.6299(2) 0.63142(13) 0.34803(7) 0.0604(6) Uani d . 1 1
H H6B 0.5954 0.6596 0.3240 0.072 Uiso calc R 1 1
C C1C 0.2735(2) 0.67433(10) 0.43362(5) 0.0394(4) Uani d . 1 1
C C2C 0.3098(3) 0.71111(13) 0.47069(6) 0.0642(6) Uani d . 1 1
H H2C 0.3878 0.7504 0.4709 0.077 Uiso calc R 1 1
C C3C 0.2359(3) 0.69245(14) 0.50755(6) 0.0712(7) Uani d . 1 1
H H3C 0.2633 0.7188 0.5328 0.085 Uiso calc R 1 1
C C4C 0.1240(3) 0.63659(14) 0.50794(7) 0.0648(6) Uani d . 1 1
H H4C 0.0707 0.6245 0.5331 0.078 Uiso calc R 1 1
C C5C 0.0896(3) 0.59846(19) 0.47187(8) 0.1050(11) Uani d . 1 1
H H5C 0.0147 0.5575 0.4721 0.126 Uiso calc R 1 1
C C6C 0.1614(3) 0.61794(17) 0.43466(7) 0.0891(9) Uani d . 1 1
H H6C 0.1324 0.5917 0.4095 0.107 Uiso calc R 1 1
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
C1 P1 C1B 107.68(9)
C1 P1 C1A 116.83(8)
C1B P1 C1A 103.53(8)
C1 P1 C1C 112.80(8)
C1B P1 C1C 107.35(8)
C1A P1 C1C 107.88(9)
C2 C1 C10 116.92(16)
C2 C1 P1 120.37(15)
C10 C1 P1 122.64(14)
O2 C2 O1 120.86(17)
O2 C2 C1 126.21(19)
O1 C2 C1 112.93(16)
O1 C4 C5 112.15(18)
O1 C4 H4E 109.2
C5 C4 H4E 109.2
O1 C4 H4D 109.2
C5 C4 H4D 109.2
H4E C4 H4D 107.9
C4 C5 H5F 109.5
C4 C5 H5D 109.5
H5F C5 H5D 109.5
C4 C5 H5E 109.5
H5F C5 H5E 109.5
H5D C5 H5E 109.5
O5 C7 O6 123.05(19)
O5 C7 C10 126.98(19)
O6 C7 C10 109.97(17)
O6 C8 C9 107.42(19)
O6 C8 H8A 110.2
C9 C8 H8A 110.2
O6 C8 H8B 110.2
C9 C8 H8B 110.2
H8A C8 H8B 108.5
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
C7 C10 C1 115.89(16)
C7 C10 H10A 108.3
C1 C10 H10A 108.3
C7 C10 H10B 108.3
C1 C10 H10B 108.3
H10A C10 H10B 107.4
C2 O1 C4 117.24(16)
C7 O6 C8 117.79(16)
C6A C1A C2A 118.75(18)
C6A C1A P1 120.03(15)
C2A C1A P1 121.15(13)
C3A C2A C1A 120.87(18)
C3A C2A H2A 119.6
C1A C2A H2A 119.6
C2A C3A C4A 119.8(2)
C2A C3A H3A 120.1
C4A C3A H3A 120.1
C5A C4A C3A 120.0(2)
C5A C4A H4A 120.0
C3A C4A H4A 120.0
C4A C5A C6A 120.3(2)
C4A C5A H5A 119.8
C6A C5A H5A 119.8
C1A C6A C5A 120.2(2)
C1A C6A H6A 119.9
C5A C6A H6A 119.9
C2B C1B C6B 119.45(19)
C2B C1B P1 122.52(16)
C6B C1B P1 117.98(15)
C1B C2B C3B 119.2(2)
C1B C2B H2B 120.4
C3B C2B H2B 120.4
C4B C3B C2B 120.9(2)
C4B C3B H3B 119.6
C2B C3B H3B 119.6
C3B C4B C5B 120.0(2)
C3B C4B H4B 120.0
C5B C4B H4B 120.0
C4B C5B C6B 120.1(2)
C4B C5B H5B 119.9
C6B C5B H5B 119.9
C5B C6B C1B 120.2(2)
C5B C6B H6B 119.9
C1B C6B H6B 119.9
C6C C1C C2C 117.32(18)
C6C C1C P1 123.35(14)
C2C C1C P1 119.27(15)
C1C C2C C3C 121.6(2)
C1C C2C H2C 119.2
C3C C2C H2C 119.2
C4C C3C C2C 120.2(2)
C4C C3C H3C 119.9
C2C C3C H3C 119.9
C5C C4C C3C 118.8(2)
C5C C4C H4C 120.6
C3C C4C H4C 120.6
C4C C5C C6C 121.2(2)
C4C C5C H5C 119.4
C6C C5C H5C 119.4
C1C C6C C5C 120.8(2)
C1C C6C H6C 119.6
C5C C6C H6C 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C1 1.7196(18) y
P1 C1B 1.8073(19) y
P1 C1A 1.8172(18) y
P1 C1C 1.8186(18) y
C1 C2 1.404(3) y
C1 C10 1.511(3) y
C2 O2 1.230(2) y
C2 O1 1.374(2) y
C4 O1 1.435(2) y
C4 C5 1.496(3) ?
C4 H4E 0.9900 ?
C4 H4D 0.9900 ?
C5 H5F 0.9800 ?
C5 H5D 0.9800 ?
C5 H5E 0.9800 ?
C7 O5 1.193(2) ?
C7 O6 1.334(2) ?
C7 C10 1.504(3) ?
C8 O6 1.451(2) ?
C8 C9 1.477(3) ?
C8 H8A 0.9900 ?
C8 H8B 0.9900 ?
C9 H9A 0.9800 ?
C9 H9B 0.9800 ?
C9 H9C 0.9800 ?
C10 H10A 0.9900 .
C10 H10B 0.9900 ?
C1A C6A 1.383(3) ?
C1A C2A 1.394(3) ?
C2A C3A 1.374(3) ?
C2A H2A 0.9500 ?
C3A C4A 1.380(3) ?
C3A H3A 0.9500 ?
C4A C5A 1.375(3) ?
C4A H4A 0.9500 ?
C5A C6A 1.385(3) ?
C5A H5A 0.9500 ?
C6A H6A 0.9500 ?
C1B C2B 1.375(3) ?
C1B C6B 1.388(3) ?
C2B C3B 1.404(3) ?
C2B H2B 0.9500 ?
C3B C4B 1.357(4) ?
C3B H3B 0.9500 ?
C4B C5B 1.367(4) ?
C4B H4B 0.9500 ?
C5B C6B 1.386(3) ?
C5B H5B 0.9500 ?
C6B H6B 0.9500 ?
C1C C6C 1.364(3) ?
C1C C2C 1.372(3) ?
C2C C3C 1.378(3) ?
C2C H2C 0.9500 ?
C3C C4C 1.356(3) ?
C3C H3C 0.9500 ?
C4C C5C 1.351(3) ?
C4C H4C 0.9500 ?
C5C C6C 1.382(3) ?
C5C H5C 0.9500 ?
C6C H6C 0.9500 ?
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
C4B H4B O2 8_755 0.95 2.46 3.389(3) 165
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
C1B P1 C1 C2 -171.83(14)
C1A P1 C1 C2 72.30(16)
C1C P1 C1 C2 -53.57(17)
C1B P1 C1 C10 11.26(17)
C1A P1 C1 C10 -104.62(15)
C1C P1 C1 C10 129.52(14)
C10 C1 C2 O2 -5.6(3)
P1 C1 C2 O2 177.28(16)
C10 C1 C2 O1 174.82(15)
P1 C1 C2 O1 -2.3(2)
O5 C7 C10 C1 -4.0(3)
O6 C7 C10 C1 175.86(16)
C2 C1 C10 C7 -81.0(2)
P1 C1 C10 C7 96.03(19)
O2 C2 O1 C4 -12.4(3)
C1 C2 O1 C4 167.14(16)
C5 C4 O1 C2 -76.2(2)
O5 C7 O6 C8 0.7(3)
C10 C7 O6 C8 -179.09(18)
C9 C8 O6 C7 169.7(2)
C1 P1 C1A C6A -8.67(19)
C1B P1 C1A C6A -126.82(17)
C1C P1 C1A C6A 119.61(16)
C1 P1 C1A C2A 168.22(15)
C1B P1 C1A C2A 50.07(17)
C1C P1 C1A C2A -63.50(17)
C6A C1A C2A C3A -1.8(3)
P1 C1A C2A C3A -178.78(16)
C1A C2A C3A C4A 0.7(3)
C2A C3A C4A C5A 0.4(4)
C3A C4A C5A C6A -0.3(4)
C2A C1A C6A C5A 2.0(3)
P1 C1A C6A C5A 178.93(18)
C4A C5A C6A C1A -0.9(4)
C1 P1 C1B C2B 106.72(17)
C1A P1 C1B C2B -128.96(17)
C1C P1 C1B C2B -15.00(19)
C1 P1 C1B C6B -71.05(17)
C1A P1 C1B C6B 53.28(17)
C1C P1 C1B C6B 167.24(15)
C6B C1B C2B C3B 0.0(3)
P1 C1B C2B C3B -177.73(17)
C1B C2B C3B C4B 1.2(4)
C2B C3B C4B C5B -0.8(4)
C3B C4B C5B C6B -0.8(4)
C4B C5B C6B C1B 2.0(4)
C2B C1B C6B C5B -1.6(3)
P1 C1B C6B C5B 176.23(17)
C1 P1 C1C C6C 151.7(2)
C1B P1 C1C C6C -89.8(2)
C1A P1 C1C C6C 21.2(2)
C1 P1 C1C C2C -31.1(2)
C1B P1 C1C C2C 87.31(18)
C1A P1 C1C C2C -161.69(16)
C6C C1C C2C C3C -0.3(4)
P1 C1C C2C C3C -177.67(18)
C1C C2C C3C C4C -0.1(4)
C2C C3C C4C C5C 1.7(4)
C3C C4C C5C C6C -2.9(5)
C2C C1C C6C C5C -0.8(4)
P1 C1C C6C C5C 176.4(2)
C4C C5C C6C C1C 2.5(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8155945
