#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/50/2015008.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_2015008
loop_
_publ_author_name
'Fernando Castañeda'
'Christian Aliaga'
'Clifford A. Bunton'
'María Teresa Garland'
'Ricardo Baggio'
_publ_section_title
;
 3-(Triphenylphosphoranylidene)pentane-2,4-dione and diethyl
 2-(triphenylphosphoranylidene)malonate
;
_journal_coeditor_code           GG1259
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o496
_journal_page_last               o499
_journal_paper_doi               10.1107/S0108270105015064
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C25 H25 O4 P'
_chemical_formula_moiety         'C25 H25 O4 P'
_chemical_formula_sum            'C25 H25 O4 P'
_chemical_formula_weight         420.42
_chemical_name_systematic
;
diethyl 2-(triphenylphosphoranylidene)malonate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.12(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.572(14)
_cell_length_b                   9.022(12)
_cell_length_c                   19.52(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      7.5
_cell_volume                     2214(4)
_computing_cell_refinement       P3/P4-PC
_computing_data_collection       'P3/P4-PC (Siemens, 1991)'
_computing_data_reduction        'XDISK in SHELXTL/PC (Sheldrick, 1991)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  SHELXL97
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'Siemens R3m'
_diffrn_measurement_method       ω/2θ
_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  0.027
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4069
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         1.62
_diffrn_standards_decay_%        1.8
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.22
_refine_ls_extinction_coef       0.0202(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.059P)²+1.0148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1287
_reflns_number_gt                3138
_reflns_number_total             3880
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg1259.cif
_cod_data_source_block           II
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015008
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_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
_atom_site_type_symbol
P1 0.28278(4) 0.23787(6) 0.08714(3) 0.03604(19) Uani d . 1 . . P
O1 0.40889(15) 0.4986(2) 0.14144(9) 0.0605(5) Uani d U 1 . . O
O2 0.32989(18) 0.4985(2) 0.24457(9) 0.0771(6) Uani d . 1 . . O
O3 0.08152(12) 0.26462(18) 0.14410(8) 0.0482(4) Uani d . 1 . . O
O4 0.11500(16) 0.4132(2) 0.23439(10) 0.0740(6) Uani d . 1 . . O
C1 0.25214(18) 0.3599(2) 0.15379(11) 0.0402(5) Uani d . 1 . . C
C2 0.3306(2) 0.4563(3) 0.18550(12) 0.0497(6) Uani d . 1 . . C
C3 0.5072(3) 0.5619(4) 0.17161(18) 0.0800(9) Uani d U 1 . . C
H3A 0.5203 0.5168 0.2159 0.096 Uiso calc R 1 . . H
H3B 0.5671 0.5394 0.1422 0.096 Uiso calc R 1 . . H
C4 0.4980(3) 0.7229(4) 0.1797(2) 0.0944(11) Uani d . 1 . . C
H4A 0.5625 0.7613 0.1993 0.142 Uiso calc R 1 . . H
H4B 0.4394 0.7452 0.2094 0.142 Uiso calc R 1 . . H
H4C 0.4861 0.7678 0.1358 0.142 Uiso calc R 1 . . H
C5 0.14746(19) 0.3514(3) 0.18333(11) 0.0451(6) Uani d . 1 . . C
C6 -0.0166(2) 0.2190(4) 0.17536(15) 0.0691(8) Uani d . 1 . . C
H6A -0.0587 0.3056 0.1869 0.083 Uiso calc R 1 . . H
H6B -0.0017 0.1651 0.2173 0.083 Uiso calc R 1 . . H
C7 -0.0765(2) 0.1240(4) 0.12803(19) 0.0892(11) Uani d . 1 . . C
H7A -0.1420 0.0942 0.1491 0.134 Uiso calc R 1 . . H
H7B -0.0351 0.0378 0.1172 0.134 Uiso calc R 1 . . H
H7C -0.0917 0.1780 0.0867 0.134 Uiso calc R 1 . . H
C11 0.23707(19) 0.0525(3) 0.11073(12) 0.0480(6) Uani d . 1 . . C
C21 0.2530(2) 0.0054(3) 0.17789(15) 0.0645(8) Uani d . 1 . . C
H21 0.2865 0.0674 0.2093 0.077 Uiso calc R 1 . . H
C31 0.2184(3) -0.1356(4) 0.1979(2) 0.0878(12) Uani d . 1 . . C
H31 0.2302 -0.1680 0.2425 0.105 Uiso calc R 1 . . H
C41 0.1674(3) -0.2260(3) 0.1521(2) 0.0973(14) Uani d . 1 . . C
H41 0.1443 -0.3194 0.1657 0.117 Uiso calc R 1 . . H
C51 0.1504(3) -0.1793(4) 0.0865(2) 0.1018(14) Uani d . 1 . . C
H51 0.1156 -0.2413 0.0556 0.122 Uiso calc R 1 . . H
C61 0.1846(3) -0.0396(3) 0.06506(16) 0.0738(9) Uani d . 1 . . C
H61 0.1723 -0.0085 0.0203 0.089 Uiso calc R 1 . . H
C12 0.22621(17) 0.2862(2) 0.00423(11) 0.0390(5) Uani d . 1 . . C
C22 0.2505(2) 0.2050(3) -0.05516(12) 0.0513(6) Uani d . 1 . . C
H22 0.2972 0.1253 -0.0526 0.062 Uiso calc R 1 . . H
C32 0.2052(2) 0.2430(3) -0.11772(13) 0.0637(8) Uani d . 1 . . C
H32 0.2206 0.1880 -0.1567 0.076 Uiso calc R 1 . . H
C42 0.1374(2) 0.3626(4) -0.12168(14) 0.0702(9) Uani d . 1 . . C
H42 0.1074 0.3886 -0.1636 0.084 Uiso calc R 1 . . H
C52 0.1137(2) 0.4444(4) -0.06362(15) 0.0670(8) Uani d . 1 . . C
H52 0.0678 0.5250 -0.0668 0.080 Uiso calc R 1 . . H
C62 0.15799(19) 0.4070(3) -0.00085(12) 0.0490(6) Uani d . 1 . . C
H62 0.1420 0.4627 0.0379 0.059 Uiso calc R 1 . . H
C13 0.42517(18) 0.2246(2) 0.07359(11) 0.0415(5) Uani d . 1 . . C
C23 0.47419(19) 0.3002(3) 0.01996(13) 0.0560(7) Uani d . 1 . . C
H23 0.4329 0.3523 -0.0114 0.067 Uiso calc R 1 . . H
C33 0.5831(2) 0.2986(4) 0.01300(14) 0.0667(8) Uani d . 1 . . C
H33 0.6148 0.3483 -0.0233 0.080 Uiso calc R 1 . . H
C43 0.6452(2) 0.2234(4) 0.05986(14) 0.0654(8) Uani d . 1 . . C
H43 0.7188 0.2231 0.0552 0.078 Uiso calc R 1 . . H
C53 0.5985(2) 0.1489(3) 0.11338(14) 0.0654(8) Uani d . 1 . . C
H53 0.6405 0.0994 0.1453 0.079 Uiso calc R 1 . . H
C63 0.4889(2) 0.1475(3) 0.11966(12) 0.0539(6) Uani d . 1 . . C
H63 0.4575 0.0945 0.1551 0.065 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 P1 C11 108.60(15) y
C1 P1 C12 115.14(16) y
C1 P1 C13 111.66(11) y
C11 P1 C12 108.71(12) y
C11 P1 C13 106.69(11) y
C12 P1 C13 105.68(13) y
C2 O1 C3 117.4(2) y
C5 O3 C6 116.4(2) y
P1 C1 C2 122.95(19) y
P1 C1 C5 117.87(17) y
C2 C1 C5 118.8(2) y
O1 C2 O2 121.2(2) ?
O1 C2 C1 112.9(2) ?
O2 C2 C1 125.9(2) ?
C4 C3 O1 111.0(3) ?
C4 C3 H3A 109.4 ?
O1 C3 H3A 109.4 ?
C4 C3 H3B 109.4 ?
O1 C3 H3B 109.4 ?
H3A C3 H3B 108.0 ?
C3 C4 H4A 109.5 ?
C3 C4 H4B 109.5 ?
H4A C4 H4B 109.5 ?
C3 C4 H4C 109.5 ?
H4A C4 H4C 109.5 ?
H4B C4 H4C 109.5 ?
O4 C5 O3 121.1(2) ?
O4 C5 C1 127.8(2) ?
O3 C5 C1 111.0(2) ?
O3 C6 C7 109.9(3) ?
O3 C6 H6A 109.7 ?
C7 C6 H6A 109.7 ?
O3 C6 H6B 109.7 ?
C7 C6 H6B 109.7 ?
H6A C6 H6B 108.2 ?
C6 C7 H7A 109.5 ?
C6 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C6 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C61 C11 C21 119.4(3) ?
C61 C11 P1 122.4(2) ?
C21 C11 P1 118.1(2) ?
C11 C21 C31 119.7(3) ?
C11 C21 H21 120.2 ?
C31 C21 H21 120.2 ?
C41 C31 C21 120.3(4) ?
C41 C31 H31 119.8 ?
C21 C31 H31 119.8 ?
C51 C41 C31 120.1(3) ?
C51 C41 H41 120.0 ?
C31 C41 H41 120.0 ?
C41 C51 C61 120.8(4) ?
C41 C51 H51 119.6 ?
C61 C51 H51 119.6 ?
C11 C61 C51 119.7(3) ?
C11 C61 H61 120.1 ?
C51 C61 H61 120.1 ?
C62 C12 C22 119.0(2) ?
C62 C12 P1 119.42(18) ?
C22 C12 P1 121.6(2) ?
C32 C22 C12 120.5(3) ?
C32 C22 H22 119.8 ?
C12 C22 H22 119.8 ?
C42 C32 C22 119.7(3) ?
C42 C32 H32 120.2 ?
C22 C32 H32 120.2 ?
C32 C42 C52 120.4(3) ?
C32 C42 H42 119.8 ?
C52 C42 H42 119.8 ?
C42 C52 C62 120.4(3) ?
C42 C52 H52 119.8 ?
C62 C52 H52 119.8 ?
C52 C62 C12 120.1(2) ?
C52 C62 H62 120.0 ?
C12 C62 H62 120.0 ?
C63 C13 C23 118.4(2) ?
C63 C13 P1 120.42(19) ?
C23 C13 P1 120.99(17) ?
C33 C23 C13 120.7(2) ?
C33 C23 H23 119.7 ?
C13 C23 H23 119.7 ?
C23 C33 C43 120.1(3) ?
C23 C33 H33 120.0 ?
C43 C33 H33 120.0 ?
C53 C43 C33 120.2(3) ?
C53 C43 H43 119.9 ?
C33 C43 H43 119.9 ?
C43 C53 C63 119.9(2) ?
C43 C53 H53 120.1 ?
C63 C53 H53 120.1 ?
C53 C63 C13 120.7(2) ?
C53 C63 H63 119.6 ?
C13 C63 H63 119.6 ?
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 . 1.748(3) y
P1 C11 . 1.828(3) y
P1 C12 . 1.819(4) y
P1 C13 . 1.814(3) y
O1 C2 . 1.363(3) y
O1 C3 . 1.482(4) y
O2 C2 . 1.214(4) y
O3 C5 . 1.372(3) y
O3 C6 . 1.438(3) y
O4 C5 . 1.214(3) y
C1 C2 . 1.453(3) y
C1 C5 . 1.440(4) y
C3 C4 . 1.466(5) y
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C6 C7 . 1.467(5) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C11 C61 . 1.384(4) ?
C11 C21 . 1.392(5) ?
C21 C31 . 1.400(4) ?
C21 H21 . 0.9300 ?
C31 C41 . 1.369(6) ?
C31 H31 . 0.9300 ?
C41 C51 . 1.364(6) ?
C41 H41 . 0.9300 ?
C51 C61 . 1.396(4) ?
C51 H51 . 0.9300 ?
C61 H61 . 0.9300 ?
C12 C62 . 1.390(3) ?
C12 C22 . 1.405(4) ?
C22 C32 . 1.389(4) ?
C22 H22 . 0.9300 ?
C32 C42 . 1.377(5) ?
C32 H32 . 0.9300 ?
C42 C52 . 1.386(5) ?
C42 H42 . 0.9300 ?
C52 C62 . 1.386(4) ?
C52 H52 . 0.9300 ?
C62 H62 . 0.9300 ?
C13 C63 . 1.389(4) ?
C13 C23 . 1.394(4) ?
C23 C33 . 1.376(4) ?
C23 H23 . 0.9300 ?
C33 C43 . 1.380(4) ?
C33 H33 . 0.9300 ?
C43 C53 . 1.375(4) ?
C43 H43 . 0.9300 ?
C53 C63 . 1.384(4) ?
C53 H53 . 0.9300 ?
C63 H63 . 0.9300 ?
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
C53 H53 O2 2_645 0.93 2.36 3.213(6) 152
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
_geom_torsion_publ_flag
P1 C1 C2 O2 -149.8(2) y
P1 C1 C5 O4 170.8(2) y
O4 C5 C1 C2 -2.3(4) ?
C5 C1 C2 O2 22.9(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 309044
