#------------------------------------------------------------------------------
#$Date: 2025-08-21 01:01:10 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301838 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/17/4321712.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4321712
loop_
_publ_author_name
'Erik D. Brady'
'Timothy P. Hanusa'
'Maren Pink'
'Victor G. Young'
_publ_section_title
;
 The First Noncoordinated Phosphonium Diylide, [Me2P(C13H8)2]-, and Its
 Ylidic and Cationic Counterparts: Synthesis, Structural Characterization,
 and Interaction with the Heavy Group 2 Metals
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6028
_journal_page_last               6037
_journal_paper_doi               10.1021/ic000838n
_journal_volume                  39
_journal_year                    2000
_chemical_formula_moiety         'C28 H24 I P'
_chemical_formula_sum            'C28 H24 I P'
_chemical_formula_weight         518.34
_chemical_name_common            98277
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.972(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3318(1)
_cell_length_b                   10.1580(1)
_cell_length_c                   14.8414(3)
_cell_measurement_reflns_used    4341
_cell_measurement_temperature    193(2)
_cell_volume                     1101.18(3)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'SMART Platform CCD, Siemens'
_diffrn_measurement_method       omega-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5585
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    1.540
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.878426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing (1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         1928
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0207
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0321P)²+0.5099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0539
_refine_ls_wR_factor_ref         0.0556
_reflns_number_gt                1705
_reflns_number_total             1928
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic000838n_1.cif
_cod_data_source_block           98277
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_database_code               4321712
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.0000 -0.25063(2) 0.2500 0.03266(10) Uani 1 2 d S . .
P1 P 0.5000 -0.02656(8) 0.2500 0.01852(17) Uani 1 2 d S . .
C1 C 0.2897(3) 0.0723(2) 0.23552(14) 0.0205(4) Uani 1 1 d . . .
C2 C 0.3082(3) 0.1902(2) 0.17365(14) 0.0205(4) Uani 1 1 d . . .
C3 C 0.3474(3) 0.1950(3) 0.08385(15) 0.0252(5) Uani 1 1 d . . .
C4 C 0.3597(3) 0.3178(3) 0.04296(17) 0.0309(5) Uani 1 1 d . . .
C5 C 0.3337(3) 0.4328(3) 0.09066(17) 0.0335(6) Uani 1 1 d . . .
C6 C 0.2882(3) 0.4287(2) 0.17944(17) 0.0308(5) Uani 1 1 d . . .
C7 C 0.2751(3) 0.3067(2) 0.22130(15) 0.0223(4) Uani 1 1 d . . .
C8 C 0.2246(3) 0.2720(2) 0.31189(15) 0.0231(5) Uani 1 1 d . . .
C9 C 0.1701(3) 0.3503(3) 0.38153(16) 0.0297(5) Uani 1 1 d . . .
C10 C 0.1228(3) 0.2906(3) 0.45990(17) 0.0334(6) Uani 1 1 d . . .
C11 C 0.1276(3) 0.1540(3) 0.46938(16) 0.0316(5) Uani 1 1 d . . .
C12 C 0.1802(3) 0.0739(3) 0.39984(15) 0.0263(5) Uani 1 1 d . . .
C13 C 0.2312(3) 0.1338(2) 0.32149(14) 0.0209(4) Uani 1 1 d . . .
C14 C 0.5003(3) -0.1347(2) 0.34557(16) 0.0262(5) Uani 1 1 d . . .
H1 H 0.207(3) 0.015(3) 0.2150(15) 0.026(6) Uiso 1 1 d . . .
H3 H 0.366(3) 0.114(3) 0.0493(18) 0.035(7) Uiso 1 1 d . . .
H4 H 0.384(4) 0.323(3) -0.013(2) 0.042(8) Uiso 1 1 d . . .
H6 H 0.268(3) 0.506(3) 0.2110(16) 0.027(6) Uiso 1 1 d . . .
H5 H 0.339(3) 0.514(3) 0.0620(17) 0.039(7) Uiso 1 1 d . . .
H9 H 0.167(4) 0.447(3) 0.3731(18) 0.044(8) Uiso 1 1 d . . .
H10 H 0.081(4) 0.339(3) 0.508(2) 0.053(9) Uiso 1 1 d . . .
H11 H 0.099(3) 0.116(3) 0.5229(17) 0.029(7) Uiso 1 1 d . . .
H12 H 0.178(3) -0.022(3) 0.4047(17) 0.037(7) Uiso 1 1 d . . .
H14A H 0.507(3) -0.086(3) 0.3985(18) 0.038(7) Uiso 1 1 d . . .
H14B H 0.386(4) -0.187(3) 0.3385(18) 0.039(7) Uiso 1 1 d . . .
H14C H 0.605(4) -0.189(3) 0.3416(19) 0.043(8) Uiso 1 1 d . . .
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 P1 C14 104.48(17) 2_655 . ?
C14 P1 C1 111.77(10) 2_655 2_655 ?
C14 P1 C1 107.37(10) . 2_655 ?
C14 P1 C1 107.37(10) 2_655 . ?
C14 P1 C1 111.77(10) . . ?
C1 P1 C1 113.73(15) 2_655 . ?
C13 C1 C2 103.30(18) . . ?
C13 C1 P1 115.01(14) . . ?
C2 C1 P1 112.51(14) . . ?
C13 C1 H1 109.3(15) . . ?
C2 C1 H1 114.0(16) . . ?
P1 C1 H1 103.1(16) . . ?
C3 C2 C7 120.7(2) . . ?
C3 C2 C1 130.1(2) . . ?
C7 C2 C1 109.23(18) . . ?
C2 C3 C4 118.4(2) . . ?
C2 C3 H3 121.2(15) . . ?
C4 C3 H3 120.4(15) . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119(2) . . ?
C3 C4 H4 120(2) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.0(16) . . ?
C4 C5 H5 119.9(16) . . ?
C5 C6 C7 118.8(2) . . ?
C5 C6 H6 120.8(15) . . ?
C7 C6 H6 120.4(15) . . ?
C6 C7 C2 120.1(2) . . ?
C6 C7 C8 130.9(2) . . ?
C2 C7 C8 109.0(2) . . ?
C9 C8 C13 120.2(2) . . ?
C9 C8 C7 130.9(2) . . ?
C13 C8 C7 108.80(19) . . ?
C10 C9 C8 118.9(2) . . ?
C10 C9 H9 122.3(16) . . ?
C8 C9 H9 118.7(16) . . ?
C9 C10 C11 121.0(2) . . ?
C9 C10 H10 122(2) . . ?
C11 C10 H10 117(2) . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 H11 119.3(16) . . ?
C10 C11 H11 119.9(16) . . ?
C13 C12 C11 118.3(2) . . ?
C13 C12 H12 120.4(15) . . ?
C11 C12 H12 121.3(15) . . ?
C12 C13 C8 120.7(2) . . ?
C12 C13 C1 129.7(2) . . ?
C8 C13 C1 109.55(18) . . ?
P1 C14 H14A 110.1(16) . . ?
P1 C14 H14B 107.5(16) . . ?
H14A C14 H14B 111(2) . . ?
P1 C14 H14C 104.5(17) . . ?
H14A C14 H14C 112(2) . . ?
H14B C14 H14C 112(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C14 1.794(2) 2_655 ?
P1 C14 1.794(2) . ?
P1 C1 1.837(2) 2_655 ?
P1 C1 1.837(2) . ?
C1 C13 1.516(3) . ?
C1 C2 1.522(3) . ?
C1 H1 0.87(3) . ?
C2 C3 1.388(3) . ?
C2 C7 1.410(3) . ?
C3 C4 1.393(4) . ?
C3 H3 0.99(3) . ?
C4 C5 1.388(4) . ?
C4 H4 0.86(3) . ?
C5 C6 1.388(4) . ?
C5 H5 0.93(3) . ?
C6 C7 1.394(3) . ?
C6 H6 0.93(3) . ?
C7 C8 1.468(3) . ?
C8 C9 1.390(3) . ?
C8 C13 1.411(3) . ?
C9 C10 1.382(4) . ?
C9 H9 0.99(3) . ?
C10 C11 1.395(4) . ?
C10 H10 0.93(3) . ?
C11 C12 1.395(3) . ?
C11 H11 0.93(3) . ?
C12 C13 1.392(3) . ?
C12 H12 0.97(3) . ?
C14 H14A 0.92(3) . ?
C14 H14B 0.99(3) . ?
C14 H14C 0.95(3) . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 P1 C1 C13 159.62(17) 2_655 . . . ?
C14 P1 C1 C13 45.6(2) . . . . ?
C1 P1 C1 C13 -76.19(16) 2_655 . . . ?
C14 P1 C1 C2 -82.48(18) 2_655 . . . ?
C14 P1 C1 C2 163.51(15) . . . . ?
C1 P1 C1 C2 41.72(13) 2_655 . . . ?
C13 C1 C2 C3 -175.6(2) . . . . ?
P1 C1 C2 C3 59.7(3) . . . . ?
C13 C1 C2 C7 3.3(2) . . . . ?
P1 C1 C2 C7 -121.30(16) . . . . ?
C7 C2 C3 C4 2.3(3) . . . . ?
C1 C2 C3 C4 -178.9(2) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -2.3(4) . . . . ?
C4 C5 C6 C7 2.2(3) . . . . ?
C5 C6 C7 C2 0.1(3) . . . . ?
C5 C6 C7 C8 -177.8(2) . . . . ?
C3 C2 C7 C6 -2.4(3) . . . . ?
C1 C2 C7 C6 178.5(2) . . . . ?
C3 C2 C7 C8 175.96(19) . . . . ?
C1 C2 C7 C8 -3.1(2) . . . . ?
C6 C7 C8 C9 2.1(4) . . . . ?
C2 C7 C8 C9 -176.0(2) . . . . ?
C6 C7 C8 C13 179.7(2) . . . . ?
C2 C7 C8 C13 1.6(2) . . . . ?
C13 C8 C9 C10 0.0(3) . . . . ?
C7 C8 C9 C10 177.4(2) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C11 C12 C13 C8 -1.8(3) . . . . ?
C11 C12 C13 C1 -178.5(2) . . . . ?
C9 C8 C13 C12 1.2(3) . . . . ?
C7 C8 C13 C12 -176.73(19) . . . . ?
C9 C8 C13 C1 178.5(2) . . . . ?
C7 C8 C13 C1 0.6(2) . . . . ?
C2 C1 C13 C12 174.7(2) . . . . ?
P1 C1 C13 C12 -62.3(3) . . . . ?
C2 C1 C13 C8 -2.3(2) . . . . ?
P1 C1 C13 C8 120.63(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139134344
