#------------------------------------------------------------------------------
#$Date: 2025-08-21 01:01:10 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301838 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/17/4321714.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_4321714
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_compound_source        'Prof. T. Hanusa - Vanderbilt'
_chemical_formula_sum            'C28 H23 P'
_chemical_formula_weight         390.43
_chemical_name_common            00032a
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 110.621(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7330(7)
_cell_length_b                   17.8237(12)
_cell_length_c                   12.3659(8)
_cell_measurement_temperature    173(2)
_cell_volume                     2007.8(2)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_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  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10376
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7474
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       Needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.994
_refine_ls_goodness_of_fit_obs   1.116
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_restrained_S_obs      1.116
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_obs          0.0442
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0627P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1132
_refine_ls_wR_factor_obs         0.1041
_reflns_number_observed          2454
_reflns_number_total             3542
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic000838n_3.cif
_cod_data_source_block           00032a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0627P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0627P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

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 

2020-11-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C56 H46 P2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     780.87
_cod_database_code               4321714
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
P1 P 0.51274(7) 0.24134(3) 0.91266(5) 0.0252(2) Uani 1 d . .
C1 C 0.6755(3) 0.18879(12) 0.9255(2) 0.0353(6) Uani 1 d . .
H1A H 0.6678(7) 0.1692(7) 0.8495(3) 0.053 Uiso 1 calc R .
H1B H 0.6858(9) 0.1469(5) 0.9791(10) 0.053 Uiso 1 calc R .
H1C H 0.7615(3) 0.2216(2) 0.9548(12) 0.053 Uiso 1 calc R .
C2 C 0.3694(3) 0.17252(12) 0.8631(2) 0.0348(6) Uani 1 d . .
H2A H 0.3646(11) 0.1534(6) 0.7876(6) 0.052 Uiso 1 calc R .
H2B H 0.2753(4) 0.1956(2) 0.8562(12) 0.052 Uiso 1 calc R .
H2C H 0.3902(9) 0.1310(4) 0.9185(7) 0.052 Uiso 1 calc R .
C3 C 0.5280(2) 0.26635(11) 1.0614(2) 0.0244(5) Uani 1 d . .
H3A H 0.5414(2) 0.22096(11) 1.1116(2) 0.029 Uiso 1 calc R .
C4 C 0.6508(3) 0.32267(12) 1.1115(2) 0.0274(5) Uani 1 d . .
C5 C 0.8004(3) 0.31251(15) 1.1531(2) 0.0392(6) Uani 1 d . .
H5A H 0.8414(3) 0.26414(15) 1.1530(2) 0.047 Uiso 1 calc R .
C6 C 0.8914(3) 0.3747(2) 1.1956(2) 0.0514(8) Uani 1 d . .
H6A H 0.9950(3) 0.3686(2) 1.2250(2) 0.062 Uiso 1 calc R .
C7 C 0.8305(3) 0.4450(2) 1.1950(2) 0.0545(8) Uani 1 d . .
H7A H 0.8937(3) 0.4869(2) 1.2223(2) 0.065 Uiso 1 calc R .
C8 C 0.6814(3) 0.45586(14) 1.1558(2) 0.0427(7) Uani 1 d . .
H8A H 0.6414(3) 0.50439(14) 1.1565(2) 0.051 Uiso 1 calc R .
C9 C 0.5897(3) 0.39395(12) 1.1148(2) 0.0300(6) Uani 1 d . .
C10 C 0.4314(3) 0.38649(12) 1.0810(2) 0.0290(5) Uani 1 d . .
C11 C 0.3231(3) 0.43865(14) 1.0796(2) 0.0392(7) Uani 1 d . .
H11A H 0.3467(3) 0.49024(14) 1.0945(2) 0.047 Uiso 1 calc R .
C12 C 0.1815(3) 0.4135(2) 1.0563(2) 0.0455(7) Uani 1 d . .
H12A H 0.1072(3) 0.4485(2) 1.0548(2) 0.055 Uiso 1 calc R .
C13 C 0.1453(3) 0.3384(2) 1.0349(2) 0.0431(7) Uani 1 d . .
H13A H 0.0474(3) 0.3224(2) 1.0209(2) 0.052 Uiso 1 calc R .
C14 C 0.2512(3) 0.28631(14) 1.0339(2) 0.0327(6) Uani 1 d . .
H14A H 0.2262(3) 0.23492(14) 1.0182(2) 0.039 Uiso 1 calc R .
C15 C 0.3930(2) 0.31057(12) 1.0561(2) 0.0255(5) Uani 1 d . .
C16 C 0.4838(2) 0.31687(12) 0.8202(2) 0.0243(5) Uani 1 d . .
C17 C 0.5953(2) 0.35903(11) 0.7938(2) 0.0244(5) Uani 1 d . .
C18 C 0.7490(3) 0.36031(12) 0.8409(2) 0.0306(6) Uani 1 d . .
H18A H 0.7990(3) 0.32964(12) 0.9057(2) 0.037 Uiso 1 calc R .
C19 C 0.8283(3) 0.40561(13) 0.7942(2) 0.0352(6) Uani 1 d . .
H19A H 0.9325(3) 0.40427(13) 0.8253(2) 0.042 Uiso 1 calc R .
C20 C 0.7580(3) 0.45362(13) 0.7016(2) 0.0379(6) Uani 1 d . .
H20A H 0.8144(3) 0.48489(13) 0.6709(2) 0.045 Uiso 1 calc R .
C21 C 0.6078(3) 0.45545(12) 0.6552(2) 0.0318(6) Uani 1 d . .
H21A H 0.5601(3) 0.48859(12) 0.5932(2) 0.038 Uiso 1 calc R .
C22 C 0.5244(2) 0.40851(12) 0.6992(2) 0.0249(5) Uani 1 d . .
C23 C 0.3688(2) 0.39852(11) 0.6669(2) 0.0252(5) Uani 1 d . .
C24 C 0.2513(3) 0.43167(12) 0.5787(2) 0.0317(6) Uani 1 d . .
H24A H 0.2695(3) 0.46756(12) 0.5286(2) 0.038 Uiso 1 calc R .
C25 C 0.1095(3) 0.41204(13) 0.5651(2) 0.0365(6) Uani 1 d . .
H25A H 0.0297(3) 0.43215(13) 0.5029(2) 0.044 Uiso 1 calc R .
C26 C 0.0834(3) 0.36217(13) 0.6435(2) 0.0350(6) Uani 1 d . .
H26A H -0.0150(3) 0.35092(13) 0.6358(2) 0.042 Uiso 1 calc R .
C27 C 0.1968(3) 0.32900(12) 0.7313(2) 0.0311(6) Uani 1 d . .
H27A H 0.1762(3) 0.29591(12) 0.7839(2) 0.037 Uiso 1 calc R .
C28 C 0.3429(2) 0.34438(11) 0.7427(2) 0.0249(5) Uani 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'
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
C16 P1 C2 112.41(11) . . ?
C16 P1 C1 113.46(11) . . ?
C2 P1 C1 103.21(12) . . ?
C16 P1 C3 114.16(10) . . ?
C2 P1 C3 106.54(10) . . ?
C1 P1 C3 106.18(10) . . ?
C15 C3 C4 102.7(2) . . ?
C15 C3 P1 108.57(14) . . ?
C4 C3 P1 109.96(14) . . ?
C5 C4 C9 120.7(2) . . ?
C5 C4 C3 130.1(2) . . ?
C9 C4 C3 109.2(2) . . ?
C4 C5 C6 118.9(2) . . ?
C7 C6 C5 120.1(3) . . ?
C8 C7 C6 121.7(3) . . ?
C7 C8 C9 118.6(3) . . ?
C8 C9 C4 120.0(2) . . ?
C8 C9 C10 130.8(2) . . ?
C4 C9 C10 108.9(2) . . ?
C11 C10 C15 119.6(2) . . ?
C11 C10 C9 131.3(2) . . ?
C15 C10 C9 108.9(2) . . ?
C12 C11 C10 118.6(2) . . ?
C11 C12 C13 121.5(2) . . ?
C12 C13 C14 120.5(2) . . ?
C15 C14 C13 118.8(2) . . ?
C14 C15 C10 121.0(2) . . ?
C14 C15 C3 129.7(2) . . ?
C10 C15 C3 109.4(2) . . ?
C17 C16 C28 106.5(2) . . ?
C17 C16 P1 126.5(2) . . ?
C28 C16 P1 126.6(2) . . ?
C18 C17 C22 117.8(2) . . ?
C18 C17 C16 133.6(2) . . ?
C22 C17 C16 108.6(2) . . ?
C19 C18 C17 120.6(2) . . ?
C18 C19 C20 121.1(2) . . ?
C21 C20 C19 119.9(2) . . ?
C20 C21 C22 120.1(2) . . ?
C21 C22 C17 120.3(2) . . ?
C21 C22 C23 131.7(2) . . ?
C17 C22 C23 108.0(2) . . ?
C24 C23 C28 120.7(2) . . ?
C24 C23 C22 131.0(2) . . ?
C28 C23 C22 108.3(2) . . ?
C25 C24 C23 119.8(2) . . ?
C24 C25 C26 119.7(2) . . ?
C27 C26 C25 121.7(2) . . ?
C26 C27 C28 119.7(2) . . ?
C27 C28 C23 118.2(2) . . ?
C27 C28 C16 133.3(2) . . ?
C23 C28 C16 108.5(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 C16 1.724(2) . ?
P1 C2 1.795(2) . ?
P1 C1 1.798(2) . ?
P1 C3 1.847(2) . ?
C3 C15 1.513(3) . ?
C3 C4 1.516(3) . ?
C4 C5 1.375(3) . ?
C4 C9 1.410(3) . ?
C5 C6 1.400(4) . ?
C6 C7 1.386(4) . ?
C7 C8 1.372(4) . ?
C8 C9 1.397(3) . ?
C9 C10 1.453(3) . ?
C10 C11 1.401(3) . ?
C10 C15 1.409(3) . ?
C11 C12 1.379(4) . ?
C12 C13 1.385(4) . ?
C13 C14 1.391(3) . ?
C14 C15 1.379(3) . ?
C16 C17 1.448(3) . ?
C16 C28 1.454(3) . ?
C17 C18 1.402(3) . ?
C17 C22 1.433(3) . ?
C18 C19 1.377(3) . ?
C19 C20 1.400(3) . ?
C20 C21 1.370(3) . ?
C21 C22 1.403(3) . ?
C22 C23 1.434(3) . ?
C23 C24 1.403(3) . ?
C23 C28 1.428(3) . ?
C24 C25 1.375(3) . ?
C25 C26 1.402(3) . ?
C26 C27 1.380(3) . ?
C27 C28 1.406(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
C16 P1 C3 C15 54.5(2) . . . . ?
C2 P1 C3 C15 -70.2(2) . . . . ?
C1 P1 C3 C15 -179.74(15) . . . . ?
C16 P1 C3 C4 -57.2(2) . . . . ?
C2 P1 C3 C4 178.1(2) . . . . ?
C1 P1 C3 C4 68.6(2) . . . . ?
C15 C3 C4 C5 168.8(2) . . . . ?
P1 C3 C4 C5 -75.8(3) . . . . ?
C15 C3 C4 C9 -9.3(2) . . . . ?
P1 C3 C4 C9 106.2(2) . . . . ?
C9 C4 C5 C6 -1.9(3) . . . . ?
C3 C4 C5 C6 -179.7(2) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C5 C6 C7 C8 1.6(4) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
C7 C8 C9 C4 -1.6(3) . . . . ?
C7 C8 C9 C10 172.0(2) . . . . ?
C5 C4 C9 C8 2.9(3) . . . . ?
C3 C4 C9 C8 -178.8(2) . . . . ?
C5 C4 C9 C10 -172.0(2) . . . . ?
C3 C4 C9 C10 6.2(2) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C4 C9 C10 C11 174.0(2) . . . . ?
C8 C9 C10 C15 -174.4(2) . . . . ?
C4 C9 C10 C15 -0.2(2) . . . . ?
C15 C10 C11 C12 1.5(3) . . . . ?
C9 C10 C11 C12 -172.2(2) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C14 -1.5(4) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C10 0.9(3) . . . . ?
C13 C14 C15 C3 179.4(2) . . . . ?
C11 C10 C15 C14 -2.1(3) . . . . ?
C9 C10 C15 C14 172.9(2) . . . . ?
C11 C10 C15 C3 179.1(2) . . . . ?
C9 C10 C15 C3 -5.9(2) . . . . ?
C4 C3 C15 C14 -169.5(2) . . . . ?
P1 C3 C15 C14 74.0(2) . . . . ?
C4 C3 C15 C10 9.1(2) . . . . ?
P1 C3 C15 C10 -107.3(2) . . . . ?
C2 P1 C16 C17 -144.4(2) . . . . ?
C1 P1 C16 C17 -27.8(2) . . . . ?
C3 P1 C16 C17 94.1(2) . . . . ?
C2 P1 C16 C28 27.0(2) . . . . ?
C1 P1 C16 C28 143.7(2) . . . . ?
C3 P1 C16 C28 -94.5(2) . . . . ?
C28 C16 C17 C18 177.2(2) . . . . ?
P1 C16 C17 C18 -9.9(4) . . . . ?
C28 C16 C17 C22 -2.5(2) . . . . ?
P1 C16 C17 C22 170.3(2) . . . . ?
C22 C17 C18 C19 -2.6(3) . . . . ?
C16 C17 C18 C19 177.7(2) . . . . ?
C17 C18 C19 C20 2.5(3) . . . . ?
C18 C19 C20 C21 -0.7(4) . . . . ?
C19 C20 C21 C22 -1.0(3) . . . . ?
C20 C21 C22 C17 0.8(3) . . . . ?
C20 C21 C22 C23 -179.2(2) . . . . ?
C18 C17 C22 C21 1.0(3) . . . . ?
C16 C17 C22 C21 -179.3(2) . . . . ?
C18 C17 C22 C23 -179.0(2) . . . . ?
C16 C17 C22 C23 0.8(2) . . . . ?
C21 C22 C23 C24 1.7(4) . . . . ?
C17 C22 C23 C24 -178.3(2) . . . . ?
C21 C22 C23 C28 -178.6(2) . . . . ?
C17 C22 C23 C28 1.3(2) . . . . ?
C28 C23 C24 C25 0.1(3) . . . . ?
C22 C23 C24 C25 179.7(2) . . . . ?
C23 C24 C25 C26 3.5(3) . . . . ?
C24 C25 C26 C27 -3.3(4) . . . . ?
C25 C26 C27 C28 -0.8(3) . . . . ?
C26 C27 C28 C23 4.4(3) . . . . ?
C26 C27 C28 C16 -176.7(2) . . . . ?
C24 C23 C28 C27 -4.1(3) . . . . ?
C22 C23 C28 C27 176.2(2) . . . . ?
C24 C23 C28 C16 176.8(2) . . . . ?
C22 C23 C28 C16 -2.9(2) . . . . ?
C17 C16 C28 C27 -175.6(2) . . . . ?
P1 C16 C28 C27 11.6(4) . . . . ?
C17 C16 C28 C23 3.3(2) . . . . ?
P1 C16 C28 C23 -169.5(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 15501957
