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#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/40/7014069.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_7014069
loop_
_publ_author_name
'Bickley, Jamie F.'
'Copsey, May C.'
'Jeffery, John C.'
'Leedham, Angela P.'
'Russell, Christopher A.'
'Stalke, Dietmar'
'Steiner, Alexander'
'Stey, Thomas'
'Zacchini, Stefano'
_publ_section_title
;
 From the tetra(amino) phosphonium cation, [P(NHPh)4]+, to the
 tetra(imino) phosphate trianion, [P(NPh)4]3-, two-faced ligands that
 bind anions and cations.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              989
_journal_page_last               995
_journal_paper_doi               10.1039/b400798k
_journal_year                    2004
_chemical_formula_sum            'C24 H24 Cl N4 P'
_chemical_formula_weight         434.89
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 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                 107.901(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.332(8)
_cell_length_b                   10.106(3)
_cell_length_c                   18.831(6)
_cell_measurement_temperature    150(2)
_cell_volume                     4587(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.939
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'Bruker APEX CCD'
_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  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4619
_diffrn_reflns_theta_full        23.29
_diffrn_reflns_theta_max         23.29
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_type   'not applied'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0374
_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)+(0.0459P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                2404
_reflns_number_total             3105
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b400798k.txt
_cod_data_source_block           1Cl
_cod_original_cell_volume        4587(3)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7014069
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_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
C11 C 0.17550(10) 0.6192(2) 0.47748(12) 0.0316(6) Uani 1 1 d . . .
C12 C 0.14260(11) 0.7258(2) 0.44667(14) 0.0398(7) Uani 1 1 d . . .
H12 H 0.1175 0.7204 0.3975 0.048 Uiso 1 1 calc R . .
C13 C 0.14625(11) 0.8408(3) 0.48761(14) 0.0437(7) Uani 1 1 d . . .
H13 H 0.1237 0.9145 0.4662 0.052 Uiso 1 1 calc R . .
C14 C 0.18221(12) 0.8497(3) 0.55897(16) 0.0519(8) Uani 1 1 d . . .
H14 H 0.1845 0.9289 0.5869 0.062 Uiso 1 1 calc R . .
C15 C 0.21464(13) 0.7429(3) 0.58928(15) 0.0603(9) Uani 1 1 d . . .
H15 H 0.2396 0.7485 0.6385 0.072 Uiso 1 1 calc R . .
C16 C 0.21146(11) 0.6281(3) 0.54944(14) 0.0454(7) Uani 1 1 d . . .
H16 H 0.2340 0.5545 0.5712 0.054 Uiso 1 1 calc R . .
C21 C 0.11483(10) 0.1950(2) 0.31025(12) 0.0304(6) Uani 1 1 d . . .
C22 C 0.12741(12) 0.0662(3) 0.33021(14) 0.0461(7) Uani 1 1 d . . .
H22 H 0.1547 0.0458 0.3762 0.055 Uiso 1 1 calc R . .
C23 C 0.10055(13) -0.0340(3) 0.28359(15) 0.0591(9) Uani 1 1 d . . .
H23 H 0.1094 -0.1234 0.2979 0.071 Uiso 1 1 calc R . .
C24 C 0.06107(12) -0.0070(3) 0.21659(14) 0.0494(7) Uani 1 1 d . . .
H24 H 0.0425 -0.0767 0.1849 0.059 Uiso 1 1 calc R . .
C25 C 0.04932(14) 0.1202(3) 0.19683(16) 0.0710(10) Uani 1 1 d . . .
H25 H 0.0222 0.1403 0.1506 0.085 Uiso 1 1 calc R . .
C26 C 0.07634(14) 0.2223(3) 0.24323(16) 0.0689(10) Uani 1 1 d . . .
H26 H 0.0680 0.3116 0.2282 0.083 Uiso 1 1 calc R . .
C31 C 0.15871(10) 0.5656(2) 0.25854(12) 0.0290(6) Uani 1 1 d . . .
C32 C 0.14585(11) 0.6626(2) 0.20396(13) 0.0384(6) Uani 1 1 d . . .
H32 H 0.1105 0.7044 0.1901 0.046 Uiso 1 1 calc R . .
C33 C 0.18491(12) 0.6981(3) 0.16978(14) 0.0469(7) Uani 1 1 d . . .
H33 H 0.1762 0.7642 0.1321 0.056 Uiso 1 1 calc R . .
C34 C 0.23601(12) 0.6390(3) 0.18978(14) 0.0457(7) Uani 1 1 d . . .
H34 H 0.2629 0.6653 0.1668 0.055 Uiso 1 1 calc R . .
C35 C 0.24830(11) 0.5414(3) 0.24325(14) 0.0416(7) Uani 1 1 d . . .
H35 H 0.2836 0.4995 0.2565 0.050 Uiso 1 1 calc R . .
C36 C 0.20994(10) 0.5037(3) 0.27788(13) 0.0372(6) Uani 1 1 d . . .
H36 H 0.2186 0.4359 0.3146 0.045 Uiso 1 1 calc R . .
C41 C 0.04038(10) 0.3863(2) 0.42401(12) 0.0332(6) Uani 1 1 d . . .
C42 C -0.01473(11) 0.4069(2) 0.41802(13) 0.0368(6) Uani 1 1 d . . .
H42 H -0.0360 0.4690 0.3828 0.044 Uiso 1 1 calc R . .
C43 C -0.03908(12) 0.3379(3) 0.46299(14) 0.0469(7) Uani 1 1 d . . .
H43 H -0.0770 0.3525 0.4588 0.056 Uiso 1 1 calc R . .
C44 C -0.00842(12) 0.2477(3) 0.51384(14) 0.0521(8) Uani 1 1 d . . .
H44 H -0.0252 0.1988 0.5442 0.063 Uiso 1 1 calc R . .
C45 C 0.04656(12) 0.2288(3) 0.52055(14) 0.0515(8) Uani 1 1 d . . .
H45 H 0.0678 0.1677 0.5564 0.062 Uiso 1 1 calc R . .
C46 C 0.07166(11) 0.2977(3) 0.47574(13) 0.0443(7) Uani 1 1 d . . .
H46 H 0.1097 0.2840 0.4806 0.053 Uiso 1 1 calc R . .
Cl1 Cl 0.2500 0.2500 0.5000 0.0740(4) Uani 1 2 d S . .
Cl2 Cl 0.0000 0.66944(8) 0.2500 0.0352(2) Uani 1 2 d S . .
N1 N 0.17344(9) 0.4976(2) 0.43847(11) 0.0329(5) Uani 1 1 d . . .
H1 H 0.1975(10) 0.438(2) 0.4598(12) 0.031(7) Uiso 1 1 d . . .
N2 N 0.14387(9) 0.2955(2) 0.36018(11) 0.0325(5) Uani 1 1 d . . .
H2 H 0.1701(9) 0.268(2) 0.3963(12) 0.025(7) Uiso 1 1 d . . .
N3 N 0.11744(9) 0.5322(2) 0.29199(10) 0.0307(5) Uani 1 1 d . . .
H3 H 0.0867(9) 0.568(2) 0.2773(10) 0.013(6) Uiso 1 1 d . . .
N4 N 0.06297(9) 0.4574(2) 0.37484(11) 0.0340(5) Uani 1 1 d . . .
H4 H 0.0445(9) 0.512(2) 0.3487(11) 0.014(6) Uiso 1 1 d . . .
P1 P 0.12440(3) 0.44587(6) 0.36664(3) 0.0292(2) Uani 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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C11 C16 119.5(2) . . ?
C12 C11 N1 122.5(2) . . ?
C16 C11 N1 118.0(2) . . ?
C11 C12 C13 119.7(2) . . ?
C14 C13 C12 120.7(3) . . ?
C15 C14 C13 119.2(3) . . ?
C14 C15 C16 120.8(3) . . ?
C15 C16 C11 120.1(3) . . ?
C26 C21 C22 119.2(2) . . ?
C26 C21 N2 122.9(2) . . ?
C22 C21 N2 117.9(2) . . ?
C21 C22 C23 119.9(2) . . ?
C22 C23 C24 121.2(3) . . ?
C25 C24 C23 118.7(3) . . ?
C24 C25 C26 120.7(3) . . ?
C21 C26 C25 120.3(3) . . ?
C36 C31 C32 120.2(2) . . ?
C36 C31 N3 122.4(2) . . ?
C32 C31 N3 117.5(2) . . ?
C33 C32 C31 119.4(2) . . ?
C34 C33 C32 120.7(2) . . ?
C33 C34 C35 119.8(2) . . ?
C34 C35 C36 120.7(3) . . ?
C35 C36 C31 119.4(2) . . ?
C46 C41 C42 120.2(2) . . ?
C46 C41 N4 121.9(2) . . ?
C42 C41 N4 117.9(2) . . ?
C43 C42 C41 120.3(2) . . ?
C44 C43 C42 119.9(3) . . ?
C45 C44 C43 119.7(2) . . ?
C44 C45 C46 121.0(3) . . ?
C41 C46 C45 118.9(3) . . ?
C11 N1 P1 127.42(18) . . ?
C21 N2 P1 127.80(18) . . ?
C31 N3 P1 128.07(18) . . ?
C41 N4 P1 128.15(19) . . ?
N2 P1 N4 113.62(11) . . ?
N2 P1 N1 101.18(12) . . ?
N4 P1 N1 114.34(11) . . ?
N2 P1 N3 113.35(11) . . ?
N4 P1 N3 101.16(11) . . ?
N1 P1 N3 113.79(11) . . ?
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
C11 C12 1.377(3) . ?
C11 C16 1.384(3) . ?
C11 N1 1.424(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.375(4) . ?
C14 C15 1.370(4) . ?
C15 C16 1.371(4) . ?
C21 C26 1.365(4) . ?
C21 C22 1.365(3) . ?
C21 N2 1.425(3) . ?
C22 C23 1.375(4) . ?
C23 C24 1.375(4) . ?
C24 C25 1.345(4) . ?
C25 C26 1.389(4) . ?
C31 C36 1.385(3) . ?
C31 C32 1.385(3) . ?
C31 N3 1.417(3) . ?
C32 C33 1.383(3) . ?
C33 C34 1.369(4) . ?
C34 C35 1.375(4) . ?
C35 C36 1.380(3) . ?
C41 C46 1.380(3) . ?
C41 C42 1.381(3) . ?
C41 N4 1.424(3) . ?
C42 C43 1.381(3) . ?
C43 C44 1.376(4) . ?
C44 C45 1.373(4) . ?
C45 C46 1.389(3) . ?
N1 P1 1.617(2) . ?
N2 P1 1.614(2) . ?
N3 P1 1.617(2) . ?
N4 P1 1.615(2) . ?
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
_geom_hbond_site_symmetry_A
N4 H4 Cl2 0.79(2) 2.45(2) 3.219(2) 167(2) .
N3 H3 Cl2 0.83(2) 2.33(2) 3.155(2) 173.4(18) .
N2 H2 Cl1 0.84(2) 2.35(2) 3.165(2) 165(2) .
N1 H1 Cl1 0.86(2) 2.31(2) 3.160(2) 168(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12995934
