#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/90/2019018.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_2019018
loop_
_publ_author_name
'Levason, William'
'Pugh, David'
'Reid, Gillian'
_publ_section_title
;
 Tribenzylphosphane and its hydrochloride salt, tribenzylphosphonium
 hydrogen dichloride--tribenzylphosphane (1/1)
;
_journal_coeditor_code           YF3030
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              560
_journal_page_last               564
_journal_paper_doi               10.1107/S0108270113010226
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C42 H43 P2 +, H Cl2 -'
_chemical_formula_moiety         'C42 H43 P2 +, H Cl2 -'
_chemical_formula_sum            'C42 H44 Cl2 P2'
_chemical_formula_weight         681.61
_chemical_name_systematic
;
Tribenzylphosphonium hydrogen dichloride--tribenzylphosphane (1/1)
;
_space_group_IT_number           146
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   13.941(5)
_cell_length_b                   13.941(5)
_cell_length_c                   15.693(7)
_cell_measurement_reflns_used    2232
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.1
_cell_volume                     2641.3(18)
_computing_cell_refinement
;
CrystalClear-SM Expert (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert (Rigaku, 2011)
;
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material
;
PLATON (Spek, 2009), WinGX (Farrugia, 2012), enCIFer (Allen
et al., 2004),
publCIF (Westrip, 2010) and Mercury (Macrae et al.,
2006).
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0492
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2521
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(CrystalClear-SM Expert; Rigaku, 2011)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.571
_refine_ls_abs_structure_details 'Flack (1983), 325 Friedel pairs'
_refine_ls_abs_structure_Flack   0.34(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1664
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0419
_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)+(0.0533P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                1414
_reflns_number_total             1664
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            yf3030.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               2019018
_cod_database_fobs_code          2019018
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.7408(4) 0.2664(3) 0.5748(2) 0.0219(9) Uani d . 1 1
H H1A 0.6962 0.1861 0.5870 0.026 Uiso calc R 1 1
H H1B 0.7503 0.2757 0.5123 0.026 Uiso calc R 1 1
C C2 0.8536(3) 0.3121(3) 0.6161(2) 0.0179(8) Uani d . 1 1
C C3 0.8675(4) 0.2586(3) 0.6871(2) 0.0188(8) Uani d . 1 1
H H3 0.8054 0.1945 0.7100 0.023 Uiso calc R 1 1
C C4 0.9695(4) 0.2979(4) 0.7236(2) 0.0246(10) Uani d . 1 1
H H4 0.9784 0.2599 0.7705 0.030 Uiso calc R 1 1
C C5 1.0613(3) 0.3944(4) 0.6917(2) 0.0215(9) Uani d . 1 1
H H5 1.1320 0.4225 0.7175 0.026 Uiso calc R 1 1
C C6 1.0482(4) 0.4478(4) 0.6232(2) 0.0228(9) Uani d . 1 1
H H6 1.1098 0.5131 0.6013 0.027 Uiso calc R 1 1
C C7 0.9445(3) 0.4062(3) 0.5858(2) 0.0209(9) Uani d . 1 1
H H7 0.9363 0.4436 0.5382 0.025 Uiso calc R 1 1
C C8 0.5926(4) 0.3968(4) 0.9179(2) 0.0238(9) Uani d . 1 1
H H8A 0.5855 0.3801 0.9796 0.029 Uiso calc R 1 1
H H8B 0.6363 0.4782 0.9109 0.029 Uiso calc R 1 1
C C9 0.4792(3) 0.3541(3) 0.8800(2) 0.0188(8) Uani d . 1 1
C C10 0.3866(3) 0.2587(3) 0.9116(2) 0.0212(9) Uani d . 1 1
H H10 0.3949 0.2210 0.9589 0.025 Uiso calc R 1 1
C C11 0.2836(4) 0.2187(4) 0.8749(2) 0.0225(9) Uani d . 1 1
H H11 0.2216 0.1535 0.8965 0.027 Uiso calc R 1 1
C C12 0.2708(3) 0.2744(4) 0.8057(2) 0.0234(9) Uani d . 1 1
H H12 0.1998 0.2482 0.7810 0.028 Uiso calc R 1 1
C C13 0.3610(4) 0.3671(4) 0.7734(2) 0.0225(10) Uani d . 1 1
H H13 0.3524 0.4043 0.7259 0.027 Uiso calc R 1 1
C C14 0.4654(4) 0.4070(4) 0.8102(2) 0.0244(10) Uani d . 1 1
H H14 0.5276 0.4708 0.7871 0.029 Uiso calc R 1 1
P P1 0.6667 0.3333 0.61180(14) 0.0249(4) Uani d S 1 3
P P2 0.6667 0.3333 0.86636(12) 0.0258(5) Uani d S 1 3
Cl Cl1 0.6667 0.3333 0.15629(12) 0.0371(5) Uani d S 1 3
Cl Cl2 0.6667 0.3333 0.35858(12) 0.0363(5) Uani d S 1 3
H H1 0.6667 0.3333 0.273(4) 0.05(2) Uiso d S 1 3
H H2 0.6667 0.3333 0.790(5) 0.064 Uiso d S 1 3
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 P1 . . 112.9(3) ?
C2 C1 H1A . . 109.0 ?
P1 C1 H1A . . 109.0 ?
C2 C1 H1B . . 109.0 ?
P1 C1 H1B . . 109.0 ?
H1A C1 H1B . . 107.8 ?
C7 C2 C3 . . 118.3(4) ?
C7 C2 C1 . . 121.4(3) ?
C3 C2 C1 . . 120.3(4) ?
C4 C3 C2 . . 120.7(4) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C5 . . 120.1(4) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C6 C5 C4 . . 119.6(4) ?
C6 C5 H5 . . 120.2 ?
C4 C5 H5 . . 120.2 ?
C5 C6 C7 . . 119.9(4) ?
C5 C6 H6 . . 120.1 ?
C7 C6 H6 . . 120.1 ?
C2 C7 C6 . . 121.5(4) ?
C2 C7 H7 . . 119.3 ?
C6 C7 H7 . . 119.3 ?
C9 C8 P2 . . 111.5(3) ?
C9 C8 H8A . . 109.3 ?
P2 C8 H8A . . 109.3 ?
C9 C8 H8B . . 109.3 ?
P2 C8 H8B . . 109.3 ?
H8A C8 H8B . . 108.0 ?
C14 C9 C10 . . 118.5(4) ?
C14 C9 C8 . . 119.9(4) ?
C10 C9 C8 . . 121.5(3) ?
C11 C10 C9 . . 120.9(4) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C10 C11 C12 . . 119.7(4) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
C13 C12 C11 . . 119.9(4) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C14 . . 120.3(4) ?
C12 C13 H13 . . 119.9 ?
C14 C13 H13 . . 119.9 ?
C9 C14 C13 . . 120.6(4) ?
C9 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C1 P1 C1 . 3_665 110.14(15) y
C1 P1 C1 . 2_655 110.14(15) ?
C1 P1 C1 3_665 2_655 110.14(15) ?
C8 P2 C8 2_655 3_665 102.28(16) ?
C8 P2 C8 2_655 . 102.28(16) ?
C8 P2 C8 3_665 . 102.28(16) y
C8 P2 H2 2_655 . 115.95(14) ?
C8 P2 H2 3_665 . 115.95(14) ?
C8 P2 H2 . . 115.95(13) y
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
C1 C2 . 1.515(5) ?
C1 P1 . 1.800(4) y
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C7 . 1.376(5) ?
C2 C3 . 1.407(5) ?
C3 C4 . 1.368(6) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.405(6) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.371(5) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.389(6) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C9 . 1.506(5) ?
C8 P2 . 1.847(4) y
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C14 . 1.386(5) ?
C9 C10 . 1.402(5) ?
C10 C11 . 1.380(6) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.397(5) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.372(6) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.397(6) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
P1 C1 3_665 1.800(4) ?
P1 C1 2_655 1.800(4) ?
P2 C8 2_655 1.847(4) ?
P2 C8 3_665 1.847(4) ?
P2 H2 . 1.19(7) y
Cl2 H1 . 1.35(7) y
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
Cl2 H1 Cl1 1.35(7) 1.83(7) 3.175(3) 180.0
P2 H2 P1 1.19(7) 2.80(7) 3.995(3) 180.0000(10)
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_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
P1 C1 C2 C7 . -83.3(4) y
P1 C1 C2 C3 . 96.5(4) y
C7 C2 C3 C4 . -1.6(6) ?
C1 C2 C3 C4 . 178.5(3) ?
C2 C3 C4 C5 . 1.8(6) ?
C3 C4 C5 C6 . -1.0(6) ?
C4 C5 C6 C7 . 0.0(6) ?
C3 C2 C7 C6 . 0.6(6) ?
C1 C2 C7 C6 . -179.5(3) ?
C5 C6 C7 C2 . 0.2(6) ?
P2 C8 C9 C14 . -88.9(4) y
P2 C8 C9 C10 . 88.5(4) y
C14 C9 C10 C11 . -0.8(6) ?
C8 C9 C10 C11 . -178.2(4) ?
C9 C10 C11 C12 . -0.6(6) ?
C10 C11 C12 C13 . 1.5(6) ?
C11 C12 C13 C14 . -0.9(6) ?
C10 C9 C14 C13 . 1.4(6) ?
C8 C9 C14 C13 . 178.8(4) ?
C12 C13 C14 C9 . -0.5(6) ?
C2 C1 P1 C1 3_665 -169.8(3) ?
C2 C1 P1 C1 2_655 68.5(4) ?
C9 C8 P2 C8 2_655 -78.7(4) ?
C9 C8 P2 C8 3_665 175.6(3) ?
