#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/50/2015007.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_2015007
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          'C23 H21 O2 P'
_chemical_formula_moiety         'C23 H21 O2 P'
_chemical_formula_sum            'C23 H21 O2 P'
_chemical_formula_weight         360.37
_chemical_name_systematic
;
3-(Triphenylphosphoranylidene)pentane-2,4-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.907(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.9365(18)
_cell_length_b                   9.6588(13)
_cell_length_c                   13.7975(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      7.5
_cell_volume                     1894.1(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 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  '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  0.013
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3480
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.55
_diffrn_standards_decay_%        1.5
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0657P)²+0.5296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1062
_reflns_number_gt                2782
_reflns_number_total             3325
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg1259.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015007
_cod_database_fobs_code          2015007
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 0.75701(3) 0.15482(5) 0.09982(3) 0.03156(14) Uani d . 1 . . P
O1 0.74640(10) -0.11796(14) 0.15677(11) 0.0497(4) Uani d . 1 . . O
O2 0.51103(10) 0.11643(19) 0.15052(13) 0.0656(5) Uani d . 1 . . O
C1 0.66098(12) 0.08708(19) 0.13182(13) 0.0345(4) Uani d . 1 . . C
C2 0.66881(14) -0.0614(2) 0.14365(14) 0.0402(4) Uani d . 1 . . C
C3 0.58424(16) -0.1502(2) 0.13719(18) 0.0583(6) Uani d . 1 . . C
H3A 0.6014 -0.2461 0.1382 0.087 Uiso calc R 1 . . H
H3B 0.5353 -0.1303 0.0750 0.087 Uiso calc R 1 . . H
H3C 0.5622 -0.1309 0.1942 0.087 Uiso calc R 1 . . H
C4 0.58568(13) 0.1682(2) 0.14904(14) 0.0424(5) Uani d . 1 . . C
C5 0.59901(17) 0.3203(2) 0.17488(19) 0.0598(6) Uani d . 1 . . C
H5A 0.5614 0.3457 0.2173 0.090 Uiso calc R 1 . . H
H5B 0.5801 0.3738 0.1133 0.090 Uiso calc R 1 . . H
H5C 0.6641 0.3380 0.2105 0.090 Uiso calc R 1 . . H
C11 0.72720(12) 0.32283(18) 0.04038(14) 0.0349(4) Uani d . 1 . . C
C21 0.65632(14) 0.3268(2) -0.05256(15) 0.0443(5) Uani d . 1 . . C
H21 0.6320 0.2444 -0.0849 0.053 Uiso calc R 1 . . H
C31 0.62158(18) 0.4514(2) -0.09754(17) 0.0575(6) Uani d . 1 . . C
H31 0.5733 0.4527 -0.1591 0.069 Uiso calc R 1 . . H
C41 0.65868(19) 0.5737(2) -0.0510(2) 0.0630(6) Uani d . 1 . . C
H41 0.6351 0.6578 -0.0810 0.076 Uiso calc R 1 . . H
C51 0.73058(17) 0.5720(2) 0.0397(2) 0.0609(6) Uani d . 1 . . C
H51 0.7560 0.6548 0.0704 0.073 Uiso calc R 1 . . H
C61 0.76510(14) 0.4472(2) 0.08556(17) 0.0479(5) Uani d . 1 . . C
H61 0.8138 0.4466 0.1468 0.057 Uiso calc R 1 . . H
C12 0.86372(13) 0.1740(2) 0.20646(15) 0.0418(4) Uani d . 1 . . C
C22 0.94271(14) 0.2464(2) 0.20004(19) 0.0570(6) Uani d . 1 . . C
H22 0.9432 0.2851 0.1385 0.068 Uiso calc R 1 . . H
C32 1.02105(16) 0.2603(3) 0.2865(2) 0.0783(9) Uani d . 1 . . C
H32 1.0740 0.3079 0.2826 0.094 Uiso calc R 1 . . H
C42 1.0197(2) 0.2032(4) 0.3777(2) 0.0883(10) Uani d . 1 . . C
H42 1.0717 0.2129 0.4353 0.106 Uiso calc R 1 . . H
C52 0.9420(2) 0.1322(3) 0.3841(2) 0.0787(8) Uani d . 1 . . C
H52 0.9419 0.0936 0.4459 0.094 Uiso calc R 1 . . H
C62 0.86397(16) 0.1179(2) 0.29932(16) 0.0550(6) Uani d . 1 . . C
H62 0.8114 0.0705 0.3044 0.066 Uiso calc R 1 . . H
C13 0.77789(12) 0.04996(18) -0.00053(13) 0.0340(4) Uani d . 1 . . C
C23 0.86351(14) 0.0511(2) -0.01979(17) 0.0523(5) Uani d . 1 . . C
H23 0.9135 0.1018 0.0220 0.063 Uiso calc R 1 . . H
C33 0.87507(17) -0.0233(3) -0.10116(19) 0.0648(7) Uani d . 1 . . C
H33 0.9327 -0.0218 -0.1138 0.078 Uiso calc R 1 . . H
C43 0.80167(17) -0.0992(2) -0.16326(17) 0.0556(6) Uani d . 1 . . C
H43 0.8103 -0.1518 -0.2162 0.067 Uiso calc R 1 . . H
C53 0.71571(16) -0.0968(2) -0.14650(16) 0.0508(5) Uani d . 1 . . C
H53 0.6654 -0.1453 -0.1898 0.061 Uiso calc R 1 . . H
C63 0.70338(14) -0.0231(2) -0.06612(14) 0.0430(5) Uani d . 1 . . C
H63 0.6448 -0.0222 -0.0556 0.052 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 110.03(8) y
C1 P1 C12 114.62(9) y
C1 P1 C13 109.22(8) y
C11 P1 C12 107.92(9) y
C11 P1 C13 103.31(8) y
C12 P1 C13 111.14(8) y
C2 C1 P1 110.80(13) y
C4 C1 P1 125.20(14) y
C2 C1 C4 123.94(17) y
O1 C2 C1 119.51(17) ?
O1 C2 C3 119.03(18) ?
C1 C2 C3 121.43(18) ?
C2 C3 H3A 109.5 ?
C2 C3 H3B 109.5 ?
H3A C3 H3B 109.5 ?
C2 C3 H3C 109.5 ?
H3A C3 H3C 109.5 ?
H3B C3 H3C 109.5 ?
O2 C4 C1 122.5(2) ?
O2 C4 C5 116.51(18) ?
C1 C4 C5 120.79(17) ?
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 ?
C21 C11 C61 118.63(17) ?
C21 C11 P1 117.00(13) ?
C61 C11 P1 124.16(14) ?
C31 C21 C11 120.89(18) ?
C31 C21 H21 119.6 ?
C11 C21 H21 119.6 ?
C41 C31 C21 119.8(2) ?
C41 C31 H31 120.1 ?
C21 C31 H31 120.1 ?
C51 C41 C31 120.2(2) ?
C51 C41 H41 119.9 ?
C31 C41 H41 119.9 ?
C41 C51 C61 120.2(2) ?
C41 C51 H51 119.9 ?
C61 C51 H51 119.9 ?
C51 C61 C11 120.26(19) ?
C51 C61 H61 119.9 ?
C11 C61 H61 119.9 ?
C62 C12 C22 119.36(19) ?
C62 C12 P1 117.38(16) ?
C22 C12 P1 123.21(17) ?
C12 C22 C32 119.7(3) ?
C12 C22 H22 120.1 ?
C32 C22 H22 120.1 ?
C42 C32 C22 119.8(3) ?
C42 C32 H32 120.1 ?
C22 C32 H32 120.1 ?
C52 C42 C32 120.5(2) ?
C52 C42 H42 119.7 ?
C32 C42 H42 119.7 ?
C42 C52 C62 120.3(3) ?
C42 C52 H52 119.8 ?
C62 C52 H52 119.8 ?
C52 C62 C12 120.3(2) ?
C52 C62 H62 119.9 ?
C12 C62 H62 119.9 ?
C23 C13 C63 118.71(17) ?
C23 C13 P1 121.80(14) ?
C63 C13 P1 119.19(13) ?
C13 C23 C33 120.3(2) ?
C13 C23 H23 119.9 ?
C33 C23 H23 119.9 ?
C43 C33 C23 120.4(2) ?
C43 C33 H33 119.8 ?
C23 C33 H33 119.8 ?
C53 C43 C33 119.5(2) ?
C53 C43 H43 120.2 ?
C33 C43 H43 120.2 ?
C43 C53 C63 120.5(2) ?
C43 C53 H53 119.7 ?
C63 C53 H53 119.7 ?
C53 C63 C13 120.51(18) ?
C53 C63 H63 119.7 ?
C13 C63 H63 119.7 ?
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 . 1.7521(18) y
P1 C11 . 1.8109(18) y
P1 C12 . 1.8159(18) y
P1 C13 . 1.8182(18) y
O1 C2 . 1.243(2) y
O2 C4 . 1.228(2) y
C1 C2 . 1.444(3) y
C1 C4 . 1.449(3) y
C2 C3 . 1.507(3) y
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C4 C5 . 1.511(3) ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
C11 C21 . 1.390(3) ?
C11 C61 . 1.391(3) ?
C21 C31 . 1.380(3) ?
C21 H21 . 0.9300 ?
C31 C41 . 1.377(3) ?
C31 H31 . 0.9300 ?
C41 C51 . 1.376(3) ?
C41 H41 . 0.9300 ?
C51 C61 . 1.385(3) ?
C51 H51 . 0.9300 ?
C61 H61 . 0.9300 ?
C12 C62 . 1.390(3) ?
C12 C22 . 1.397(3) ?
C22 C32 . 1.397(3) ?
C22 H22 . 0.9300 ?
C32 C42 . 1.380(4) ?
C32 H32 . 0.9300 ?
C42 C52 . 1.374(4) ?
C42 H42 . 0.9300 ?
C52 C62 . 1.381(3) ?
C52 H52 . 0.9300 ?
C62 H62 . 0.9300 ?
C13 C23 . 1.384(3) ?
C13 C63 . 1.391(3) ?
C23 C33 . 1.387(3) ?
C23 H23 . 0.9300 ?
C33 C43 . 1.377(3) ?
C33 H33 . 0.9300 ?
C43 C53 . 1.373(3) ?
C43 H43 . 0.9300 ?
C53 C63 . 1.377(3) ?
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
C31 H31 O2 4_565 0.93 2.59 3.422(3) 149
C63 H63 O2 3_655 0.93 2.47 3.183(2) 134
C51 H51 O1 1_565 0.93 2.52 3.376(3) 153
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 O1 18.2(2) y
P1 C1 C4 O2 164.61(16) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2106316
