#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/71/2217198.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_2217198
loop_
_publ_author_name
'Wang, Aichen'
'Wang, Qibao'
'Li, Xiaoyan'
_publ_section_title
;
 (2,5-Diphenylpent-4-yn-1-en-3-ylidene)triphenylphosphorane
;
_journal_coeditor_code           LW2053
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o68
_journal_page_last               o68
_journal_paper_doi               10.1107/S1600536807062034
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C35 H27 P'
_chemical_formula_moiety         'C35 H27 P'
_chemical_formula_sum            'C35 H27 P'
_chemical_formula_weight         478.54
_chemical_name_systematic
;
(2,5-Diphenylpent-4-yn-1-en-3-ylidene)triphenylphosphorane
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                116.00(3)
_cell_angle_beta                 97.24(3)
_cell_angle_gamma                108.47(3)
_cell_formula_units_Z            2
_cell_length_a                   11.439(2)
_cell_length_b                   11.609(2)
_cell_length_c                   11.913(2)
_cell_measurement_reflns_used    5612
_cell_measurement_temperature    383(2)
_cell_measurement_theta_max      23.23
_cell_measurement_theta_min      2.21
_cell_volume                     1281.9(7)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction
'SAINT (Bruker, 2001) and SHELXTL (Sheldrick, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      383(2)
_diffrn_measured_fraction_theta_full 1.97
_diffrn_measured_fraction_theta_max 1.97
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_method       'ω scans'
_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  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9166
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        0.015
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.9721
_exptl_absorpt_correction_T_min  0.9659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            'Purple red'
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.293
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         4661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                4077
_reflns_number_total             4661
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            lw2053.cif
_cod_data_source_block           I
_cod_original_cell_volume        1281.9(4)
_cod_database_code               2217198
_cod_database_fobs_code          2217198
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_occupancy
P P1 0.68533(3) 0.36252(4) 0.11133(3) 0.01164(15) Uani d 1
C C1 0.56521(14) 0.24722(17) -0.05062(14) 0.0144(3) Uani d 1
C C2 0.47129(15) 0.11909(18) -0.07668(15) 0.0164(3) Uani d 1
C C3 0.38692(16) 0.02065(19) -0.20295(16) 0.0187(4) Uani d 1
C C4 0.39421(15) 0.04989(18) -0.30372(15) 0.0193(4) Uani d 1
C C5 0.48380(16) 0.1796(2) -0.27692(16) 0.0206(4) Uani d 1
C C6 0.56947(15) 0.27875(19) -0.15066(15) 0.0168(3) Uani d 1
C C7 0.76840(14) 0.52987(17) 0.12146(14) 0.0147(3) Uani d 1
C C8 0.74427(15) 0.64557(19) 0.19848(16) 0.0188(4) Uani d 1
C C9 0.80051(17) 0.7702(2) 0.19820(18) 0.0242(4) Uani d 1
C C10 0.88218(17) 0.7816(2) 0.12299(18) 0.0243(4) Uani d 1
C C11 0.90960(16) 0.6678(2) 0.04955(16) 0.0223(4) Uani d 1
C C12 0.85367(15) 0.54293(18) 0.04849(15) 0.0163(3) Uani d 1
C C13 0.80689(14) 0.29439(18) 0.11596(14) 0.0142(3) Uani d 1
C C14 0.92794(15) 0.38344(19) 0.21428(15) 0.0163(3) Uani d 1
C C15 1.01613(16) 0.3280(2) 0.22863(16) 0.0197(4) Uani d 1
C C16 0.98606(16) 0.1863(2) 0.14545(17) 0.0222(4) Uani d 1
C C17 0.86805(17) 0.0994(2) 0.04615(17) 0.0224(4) Uani d 1
C C18 0.77842(16) 0.15322(18) 0.03089(16) 0.0191(4) Uani d 1
C C19 0.61694(14) 0.36449(17) 0.23325(14) 0.0135(3) Uani d 1
C C20 0.68991(14) 0.36051(16) 0.33433(14) 0.0132(3) Uani d 1
C C21 0.75197(14) 0.35583(17) 0.42069(14) 0.0156(3) Uani d 1
C C22 0.80550(14) 0.30986(17) 0.49926(14) 0.0153(3) Uani d 1
C C23 0.90307(15) 0.26281(19) 0.47269(16) 0.0199(4) Uani d 1
C C24 0.94525(16) 0.2043(2) 0.53938(17) 0.0232(4) Uani d 1
C C25 0.89336(17) 0.1928(2) 0.63495(16) 0.0233(4) Uani d 1
C C26 0.80095(17) 0.24431(19) 0.66597(16) 0.0211(4) Uani d 1
C C27 0.75698(15) 0.30231(18) 0.59963(15) 0.0182(3) Uani d 1
C C28 0.48816(14) 0.36477(17) 0.22947(14) 0.0142(3) Uani d 1
C C29 0.42860(16) 0.4080(2) 0.16165(16) 0.0205(4) Uani d 1
C C30 0.41673(14) 0.30236(17) 0.30066(14) 0.0143(3) Uani d 1
C C31 0.34931(15) 0.36725(18) 0.37822(15) 0.0167(3) Uani d 1
C C32 0.27977(15) 0.30599(19) 0.44037(16) 0.0199(4) Uani d 1
C C33 0.27776(17) 0.1813(2) 0.42805(17) 0.0234(4) Uani d 1
C C34 0.34548(17) 0.1160(2) 0.35238(18) 0.0233(4) Uani d 1
C C35 0.41519(15) 0.17774(18) 0.29087(15) 0.0185(3) Uani d 1
H H21 0.3514(19) 0.457(2) 0.3947(19) 0.024(5) Uiso d 1
H H5 0.630(2) 0.366(2) -0.1330(17) 0.017(4) Uiso d 1
H H1 0.4642(19) 0.099(2) -0.0043(18) 0.021(5) Uiso d 1
H H14 0.844(2) 0.003(3) -0.013(2) 0.042(6) Uiso d 1
H H2 0.328(2) -0.064(2) -0.2167(19) 0.025(5) Uiso d 1
H H6 0.691(2) 0.639(2) 0.2514(19) 0.023(5) Uiso d 1
H H23 0.229(2) 0.134(2) 0.4727(19) 0.027(5) Uiso d 1
H H11 0.9484(19) 0.480(2) 0.2726(19) 0.021(5) Uiso d 1
H H3 0.338(2) -0.017(2) -0.390(2) 0.023(5) Uiso d 1
H H10 0.871(2) 0.462(3) -0.004(2) 0.030(5) Uiso d 1
H H16 0.9390(19) 0.268(2) 0.4059(19) 0.021(5) Uiso d 1
H H24 0.348(2) 0.034(3) 0.343(2) 0.032(6) Uiso d 1
H H19 0.768(2) 0.240(2) 0.735(2) 0.028(5) Uiso d 1
H H27 0.475(2) 0.451(2) 0.1141(19) 0.025(5) Uiso d 1
H H4 0.487(2) 0.202(2) -0.345(2) 0.028(5) Uiso d 1
H H15 0.698(2) 0.092(2) -0.0382(19) 0.021(5) Uiso d 1
H H18 0.921(2) 0.153(2) 0.682(2) 0.029(5) Uiso d 1
H H13 1.050(2) 0.147(2) 0.1566(19) 0.027(5) Uiso d 1
H H12 1.095(2) 0.388(2) 0.295(2) 0.025(5) Uiso d 1
H H22 0.234(2) 0.355(2) 0.496(2) 0.028(5) Uiso d 1
H H25 0.461(2) 0.133(3) 0.238(2) 0.034(6) Uiso d 1
H H7 0.787(2) 0.853(3) 0.255(2) 0.042(6) Uiso d 1
H H20 0.693(2) 0.338(2) 0.621(2) 0.031(5) Uiso d 1
H H17 1.009(2) 0.167(2) 0.513(2) 0.032(6) Uiso d 1
H H8 0.924(2) 0.870(3) 0.125(2) 0.032(6) Uiso d 1
H H9 0.966(2) 0.670(3) 0.001(2) 0.033(6) Uiso d 1
H H26 0.339(2) 0.390(2) 0.1535(18) 0.022(5) Uiso d 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'
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
C19 P1 C13 108.20(7) y
C19 P1 C7 117.53(8) y
C13 P1 C7 105.18(7) y
C19 P1 C1 111.39(7) y
C13 P1 C1 107.73(7) y
C7 P1 C1 106.29(8) y
C6 C1 C2 119.66(15) ?
C6 C1 P1 121.88(13) ?
C2 C1 P1 118.32(12) ?
C3 C2 C1 120.33(15) ?
C3 C2 H1 119.9(12) ?
C1 C2 H1 119.8(12) ?
C4 C3 C2 119.99(17) ?
C4 C3 H2 122.2(12) ?
C2 C3 H2 117.8(12) ?
C3 C4 C5 119.77(16) ?
C3 C4 H3 120.6(13) ?
C5 C4 H3 119.6(13) ?
C4 C5 C6 120.66(16) ?
C4 C5 H4 120.6(13) ?
C6 C5 H4 118.8(13) ?
C1 C6 C5 119.49(16) ?
C1 C6 H5 120.1(11) ?
C5 C6 H5 120.4(11) ?
C8 C7 C12 119.35(16) ?
C8 C7 P1 120.06(12) ?
C12 C7 P1 120.55(13) ?
C9 C8 C7 119.84(15) ?
C9 C8 H6 120.2(13) ?
C7 C8 H6 119.9(13) ?
C8 C9 C10 120.66(16) ?
C8 C9 H7 119.9(15) ?
C10 C9 H7 119.4(15) ?
C11 C10 C9 119.51(18) ?
C11 C10 H8 119.9(13) ?
C9 C10 H8 120.5(12) ?
C12 C11 C10 120.36(16) ?
C12 C11 H9 116.2(15) ?
C10 C11 H9 123.4(15) ?
C11 C12 C7 120.22(16) ?
C11 C12 H10 120.6(14) ?
C7 C12 H10 119.1(14) ?
C18 C13 C14 120.01(15) ?
C18 C13 P1 120.91(12) ?
C14 C13 P1 118.87(12) ?
C15 C14 C13 119.37(16) ?
C15 C14 H11 119.8(12) ?
C13 C14 H11 120.7(12) ?
C14 C15 C16 120.36(16) ?
C14 C15 H12 117.8(13) ?
C16 C15 H12 121.8(13) ?
C17 C16 C15 120.25(15) ?
C17 C16 H13 120.0(12) ?
C15 C16 H13 119.8(13) ?
C16 C17 C18 120.08(17) ?
C16 C17 H14 123.3(15) ?
C18 C17 H14 116.6(15) ?
C17 C18 C13 119.88(16) ?
C17 C18 H15 118.6(12) ?
C13 C18 H15 121.5(12) ?
C20 C19 C28 121.62(13) ?
C20 C19 P1 115.92(10) ?
C28 C19 P1 122.42(11) ?
C21 C20 C19 179.42(18) y
C20 C21 C22 164.32(18) y
C23 C22 C27 118.19(15) ?
C23 C22 C21 120.51(14) ?
C27 C22 C21 121.19(14) ?
C24 C23 C22 120.55(15) ?
C24 C23 H16 119.4(12) ?
C22 C23 H16 120.1(12) ?
C23 C24 C25 120.65(15) ?
C23 C24 H17 117.8(13) ?
C25 C24 H17 121.4(13) ?
C26 C25 C24 119.34(16) ?
C26 C25 H18 118.5(12) ?
C24 C25 H18 122.1(12) ?
C27 C26 C25 120.76(15) ?
C27 C26 H19 120.4(13) ?
C25 C26 H19 118.8(13) ?
C26 C27 C22 120.41(15) ?
C26 C27 H20 121.1(13) ?
C22 C27 H20 118.5(13) ?
C29 C28 C19 125.09(15) ?
C29 C28 C30 118.87(14) ?
C19 C28 C30 115.91(13) ?
C28 C29 H27 120.4(11) ?
C28 C29 H26 118.9(12) ?
H27 C29 H26 120.5(16) ?
C35 C30 C31 118.12(15) ?
C35 C30 C28 120.97(13) ?
C31 C30 C28 120.91(15) ?
C32 C31 C30 120.45(16) ?
C32 C31 H21 116.8(12) ?
C30 C31 H21 122.6(12) ?
C33 C32 C31 120.64(15) ?
C33 C32 H22 120.8(13) ?
C31 C32 H22 118.5(13) ?
C32 C33 C34 119.68(16) ?
C32 C33 H23 122.9(12) ?
C34 C33 H23 117.5(12) ?
C35 C34 C33 119.51(18) ?
C35 C34 H24 118.0(13) ?
C33 C34 H24 122.4(14) ?
C34 C35 C30 121.56(15) ?
C34 C35 H25 119.7(14) ?
C30 C35 H25 118.7(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C19 1.7294(15) y
P1 C13 1.8104(15) y
P1 C7 1.8132(18) y
P1 C1 1.8178(19) y
C1 C6 1.394(2) ?
C1 C2 1.401(2) ?
C2 C3 1.389(2) ?
C2 H1 0.99(2) ?
C3 C4 1.388(2) ?
C3 H2 0.92(2) ?
C4 C5 1.392(3) ?
C4 H3 0.95(2) ?
C5 C6 1.394(3) ?
C5 H4 0.96(2) ?
C6 H5 0.94(2) ?
C7 C8 1.393(2) ?
C7 C12 1.402(2) ?
C8 C9 1.387(3) ?
C8 H6 0.94(2) ?
C9 C10 1.389(3) ?
C9 H7 0.98(2) ?
C10 C11 1.388(3) ?
C10 H8 0.97(3) ?
C11 C12 1.381(3) ?
C11 H9 0.92(2) ?
C12 H10 0.97(2) ?
C13 C18 1.393(2) ?
C13 C14 1.407(2) ?
C14 C15 1.388(2) ?
C14 H11 0.95(2) ?
C15 C16 1.390(3) ?
C15 H12 0.93(2) ?
C16 C17 1.388(3) ?
C16 H13 1.00(2) ?
C17 C18 1.390(2) ?
C17 H14 0.95(3) ?
C18 H15 0.95(2) ?
C19 C20 1.403(2) ?
C19 C28 1.4693(19) ?
C20 C21 1.206(2) y
C21 C22 1.427(2) ?
C22 C23 1.403(2) ?
C22 C27 1.405(2) ?
C23 C24 1.382(2) ?
C23 H16 0.96(2) ?
C24 C25 1.385(3) ?
C24 H17 0.98(2) ?
C25 C26 1.384(2) ?
C25 H18 0.95(2) ?
C26 C27 1.383(2) ?
C26 H19 0.96(2) ?
C27 H20 0.96(2) ?
C28 C29 1.343(2) y
C28 C30 1.500(2) ?
C29 H27 1.00(2) ?
C29 H26 0.96(2) ?
C30 C35 1.394(2) ?
C30 C31 1.398(2) ?
C31 C32 1.392(2) ?
C31 H21 0.96(2) ?
C32 C33 1.382(3) ?
C32 H22 0.99(2) ?
C33 C34 1.391(2) ?
C33 H23 1.02(2) ?
C34 C35 1.390(2) ?
C34 H24 0.92(2) ?
C35 H25 0.96(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119550
