#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/68/7106840.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_7106840
loop_
_publ_author_name
'Olga Ekkert'
'Gerald Kehr'
'Roland Frohlich'
'Gerhard Erker'
_publ_section_title
;
 Phosphirenium-borate zwitterion: formation in the 1,1-carboboration
 reaction of phosphinylalkynes
;
_journal_name_full               Chem.Commun.
_journal_page_first              10482
_journal_paper_doi               10.1039/c1cc13008k
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C27 H29 P'
_chemical_formula_weight         384.47
_chemical_name_systematic
;
?
;
_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                96.462(2)
_cell_angle_beta                 107.570(4)
_cell_angle_gamma                109.165(4)
_cell_formula_units_Z            2
_cell_length_a                   10.1751(5)
_cell_length_b                   10.6783(4)
_cell_length_c                   11.6493(7)
_cell_measurement_reflns_used    3486
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     1107.88(11)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15949
_diffrn_reflns_theta_full        66.89
_diffrn_reflns_theta_max         66.89
_diffrn_reflns_theta_min         4.10
_exptl_absorpt_coefficient_mu    1.142
_exptl_absorpt_correction_T_max  0.9451
_exptl_absorpt_correction_T_min  0.7633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0665P)²+0.4553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1227
_reflns_number_gt                3388
_reflns_number_total             3784
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc13008k.txt
_cod_data_source_block           erk5812
_cod_original_cell_volume        1107.87(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7106840
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
P1 P 0.31544(5) 0.63889(5) 0.17816(4) 0.03461(16) Uani 1 1 d . . .
C1 C 0.4790(2) 0.66526(19) 0.30368(17) 0.0397(4) Uani 1 1 d . . .
C2 C 0.5900(2) 0.6579(2) 0.37232(17) 0.0404(4) Uani 1 1 d . . .
C3 C 0.7278(2) 0.65474(18) 0.44971(16) 0.0373(4) Uani 1 1 d . . .
C4 C 0.8574(2) 0.7122(2) 0.42527(18) 0.0448(5) Uani 1 1 d . . .
H4 H 0.8549 0.7554 0.3591 0.054 Uiso 1 1 calc R . .
C5 C 0.9896(2) 0.7064(2) 0.49711(18) 0.0471(5) Uani 1 1 d . . .
H5 H 1.0759 0.7454 0.4787 0.057 Uiso 1 1 calc R . .
C6 C 0.9981(2) 0.64450(19) 0.59583(17) 0.0408(4) Uani 1 1 d . . .
C7 C 0.8691(2) 0.5866(2) 0.61995(17) 0.0436(5) Uani 1 1 d . . .
H7 H 0.8725 0.5436 0.6863 0.052 Uiso 1 1 calc R . .
C8 C 0.7353(2) 0.5907(2) 0.54844(17) 0.0421(4) Uani 1 1 d . . .
H8 H 0.6489 0.5503 0.5663 0.051 Uiso 1 1 calc R . .
C9 C 1.1442(2) 0.6413(2) 0.6742(2) 0.0550(5) Uani 1 1 d . . .
H9A H 1.2061 0.7298 0.7306 0.082 Uiso 1 1 calc R . .
H9B H 1.1950 0.6197 0.6212 0.082 Uiso 1 1 calc R . .
H9C H 1.1257 0.5724 0.7213 0.082 Uiso 1 1 calc R . .
C11 C 0.40683(19) 0.68960(18) 0.06647(15) 0.0333(4) Uani 1 1 d . . .
C12 C 0.5136(2) 0.82120(18) 0.08397(17) 0.0369(4) Uani 1 1 d . . .
C13 C 0.5785(2) 0.8470(2) -0.00457(18) 0.0435(5) Uani 1 1 d . . .
H13 H 0.6479 0.9351 0.0061 0.052 Uiso 1 1 calc R . .
C14 C 0.5447(2) 0.7474(2) -0.10800(18) 0.0459(5) Uani 1 1 d . . .
C15 C 0.4422(2) 0.6191(2) -0.12232(17) 0.0426(4) Uani 1 1 d . . .
H15 H 0.4192 0.5503 -0.1915 0.051 Uiso 1 1 calc R . .
C16 C 0.3716(2) 0.58753(18) -0.03790(16) 0.0362(4) Uani 1 1 d . . .
C17 C 0.5624(2) 0.9353(2) 0.19563(19) 0.0478(5) Uani 1 1 d . . .
H17A H 0.6305 1.0182 0.1862 0.072 Uiso 1 1 calc R . .
H17B H 0.6123 0.9110 0.2696 0.072 Uiso 1 1 calc R . .
H17C H 0.4758 0.9500 0.2028 0.072 Uiso 1 1 calc R . .
C18 C 0.6188(3) 0.7766(3) -0.2020(2) 0.0717(7) Uani 1 1 d . . .
H18A H 0.7007 0.7455 -0.1850 0.108 Uiso 1 1 calc R . .
H18B H 0.6566 0.8739 -0.1967 0.108 Uiso 1 1 calc R . .
H18C H 0.5466 0.7290 -0.2845 0.108 Uiso 1 1 calc R . .
C19 C 0.2585(2) 0.44436(19) -0.06568(18) 0.0458(5) Uani 1 1 d . . .
H19A H 0.2626 0.4162 0.0112 0.069 Uiso 1 1 calc R . .
H19B H 0.2807 0.3829 -0.1178 0.069 Uiso 1 1 calc R . .
H19C H 0.1594 0.4419 -0.1083 0.069 Uiso 1 1 calc R . .
C21 C 0.24189(19) 0.76990(18) 0.21331(16) 0.0343(4) Uani 1 1 d . . .
C22 C 0.1342(2) 0.78320(19) 0.11065(17) 0.0390(4) Uani 1 1 d . . .
C23 C 0.0610(2) 0.8683(2) 0.12914(19) 0.0446(5) Uani 1 1 d . . .
H23 H -0.0101 0.8764 0.0601 0.053 Uiso 1 1 calc R . .
C24 C 0.0887(2) 0.9415(2) 0.2452(2) 0.0449(5) Uani 1 1 d . . .
C25 C 0.1925(2) 0.9258(2) 0.34480(19) 0.0440(5) Uani 1 1 d . . .
H25 H 0.2130 0.9751 0.4245 0.053 Uiso 1 1 calc R . .
C26 C 0.2684(2) 0.84070(19) 0.33302(17) 0.0381(4) Uani 1 1 d . . .
C27 C 0.0923(2) 0.7069(2) -0.02001(18) 0.0520(5) Uani 1 1 d . . .
H27A H -0.0011 0.7094 -0.0718 0.078 Uiso 1 1 calc R . .
H27B H 0.0809 0.6129 -0.0211 0.078 Uiso 1 1 calc R . .
H27C H 0.1700 0.7492 -0.0514 0.078 Uiso 1 1 calc R . .
C28 C 0.0076(3) 1.0335(3) 0.2623(3) 0.0658(7) Uani 1 1 d . . .
H28A H -0.0061 1.0341 0.3412 0.099 Uiso 1 1 calc R . .
H28B H -0.0889 1.0003 0.1958 0.099 Uiso 1 1 calc R . .
H28C H 0.0658 1.1254 0.2610 0.099 Uiso 1 1 calc R . .
C29 C 0.3707(2) 0.8255(2) 0.45036(17) 0.0479(5) Uani 1 1 d . . .
H29A H 0.3664 0.8784 0.5216 0.072 Uiso 1 1 calc R . .
H29B H 0.4721 0.8583 0.4516 0.072 Uiso 1 1 calc R . .
H29C H 0.3392 0.7302 0.4533 0.072 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.2955 0.4335 '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
C1 P1 C11 96.85(8) . . ?
C1 P1 C21 109.04(8) . . ?
C11 P1 C21 106.90(8) . . ?
C2 C1 P1 165.01(17) . . ?
C1 C2 C3 176.1(2) . . ?
C4 C3 C8 118.20(17) . . ?
C4 C3 C2 120.19(17) . . ?
C8 C3 C2 121.57(17) . . ?
C5 C4 C3 120.65(18) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.40(19) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 118.08(17) . . ?
C7 C6 C9 121.44(18) . . ?
C5 C6 C9 120.48(19) . . ?
C6 C7 C8 121.33(17) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C3 120.33(18) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C16 C11 C12 119.47(16) . . ?
C16 C11 P1 116.78(13) . . ?
C12 C11 P1 123.67(13) . . ?
C13 C12 C11 118.79(17) . . ?
C13 C12 C17 118.16(17) . . ?
C11 C12 C17 123.04(16) . . ?
C14 C13 C12 122.35(18) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
C15 C14 C13 117.98(18) . . ?
C15 C14 C18 120.4(2) . . ?
C13 C14 C18 121.6(2) . . ?
C14 C15 C16 122.35(18) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
C15 C16 C11 119.03(17) . . ?
C15 C16 C19 117.32(17) . . ?
C11 C16 C19 123.64(17) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C26 C21 C22 118.71(16) . . ?
C26 C21 P1 125.48(14) . . ?
C22 C21 P1 115.17(13) . . ?
C23 C22 C21 119.64(17) . . ?
C23 C22 C27 117.41(17) . . ?
C21 C22 C27 122.94(16) . . ?
C24 C23 C22 122.45(18) . . ?
C24 C23 H23 118.8 . . ?
C22 C23 H23 118.8 . . ?
C23 C24 C25 117.22(17) . . ?
C23 C24 C28 121.3(2) . . ?
C25 C24 C28 121.53(19) . . ?
C24 C25 C26 123.29(18) . . ?
C24 C25 H25 118.4 . . ?
C26 C25 H25 118.4 . . ?
C25 C26 C21 118.64(17) . . ?
C25 C26 C29 117.70(16) . . ?
C21 C26 C29 123.63(16) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
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 C1 1.7657(19) . ?
P1 C11 1.8464(17) . ?
P1 C21 1.8515(18) . ?
C1 C2 1.204(3) . ?
C2 C3 1.433(3) . ?
C3 C4 1.390(3) . ?
C3 C8 1.398(3) . ?
C4 C5 1.379(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.383(3) . ?
C6 C9 1.505(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.9400 . ?
C8 H8 0.9400 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C11 C16 1.406(2) . ?
C11 C12 1.413(3) . ?
C12 C13 1.390(3) . ?
C12 C17 1.509(3) . ?
C13 C14 1.386(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.378(3) . ?
C14 C18 1.512(3) . ?
C15 C16 1.393(3) . ?
C15 H15 0.9400 . ?
C16 C19 1.508(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C21 C26 1.411(3) . ?
C21 C22 1.414(2) . ?
C22 C23 1.388(3) . ?
C22 C27 1.504(3) . ?
C23 C24 1.380(3) . ?
C23 H23 0.9400 . ?
C24 C25 1.383(3) . ?
C24 C28 1.507(3) . ?
C25 C26 1.392(3) . ?
C25 H25 0.9400 . ?
C26 C29 1.510(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 H27C 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 H28C 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 H29C 0.9700 . ?
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
C11 P1 C1 C2 -68.9(7) . . . . ?
C21 P1 C1 C2 -179.4(7) . . . . ?
P1 C1 C2 C3 86(3) . . . . ?
C1 C2 C3 C4 -5(3) . . . . ?
C1 C2 C3 C8 177(3) . . . . ?
C8 C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C4 C5 -178.23(18) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C4 C5 C6 C9 -179.06(19) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C9 C6 C7 C8 179.43(18) . . . . ?
C6 C7 C8 C3 -0.3(3) . . . . ?
C4 C3 C8 C7 0.6(3) . . . . ?
C2 C3 C8 C7 178.56(17) . . . . ?
C1 P1 C11 C16 115.08(14) . . . . ?
C21 P1 C11 C16 -132.59(13) . . . . ?
C1 P1 C11 C12 -61.65(16) . . . . ?
C21 P1 C11 C12 50.68(16) . . . . ?
C16 C11 C12 C13 1.5(2) . . . . ?
P1 C11 C12 C13 178.13(13) . . . . ?
C16 C11 C12 C17 -177.64(16) . . . . ?
P1 C11 C12 C17 -1.0(2) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C17 C12 C13 C14 177.74(18) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C12 C13 C14 C18 -178.71(19) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C18 C14 C15 C16 179.81(19) . . . . ?
C14 C15 C16 C11 -0.7(3) . . . . ?
C14 C15 C16 C19 178.38(17) . . . . ?
C12 C11 C16 C15 -0.5(2) . . . . ?
P1 C11 C16 C15 -177.34(13) . . . . ?
C12 C11 C16 C19 -179.47(16) . . . . ?
P1 C11 C16 C19 3.7(2) . . . . ?
C1 P1 C21 C26 -24.43(18) . . . . ?
C11 P1 C21 C26 -128.13(16) . . . . ?
C1 P1 C21 C22 164.93(13) . . . . ?
C11 P1 C21 C22 61.24(15) . . . . ?
C26 C21 C22 C23 2.1(3) . . . . ?
P1 C21 C22 C23 173.38(14) . . . . ?
C26 C21 C22 C27 -176.97(18) . . . . ?
P1 C21 C22 C27 -5.7(2) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C27 C22 C23 C24 178.94(19) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
C22 C23 C24 C28 179.8(2) . . . . ?
C23 C24 C25 C26 -0.2(3) . . . . ?
C28 C24 C25 C26 179.19(19) . . . . ?
C24 C25 C26 C21 2.1(3) . . . . ?
C24 C25 C26 C29 -175.74(18) . . . . ?
C22 C21 C26 C25 -3.0(3) . . . . ?
P1 C21 C26 C25 -173.29(14) . . . . ?
C22 C21 C26 C29 174.71(18) . . . . ?
P1 C21 C26 C29 4.4(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653330
