#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:18:03 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179054 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/16/4301660.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_4301660
loop_
_publ_author_name
'Allen T. Ekubo'
'Mark R. J. Elsegood'
'Andrew J. Lake'
'Martin B. Smith'
_publ_section_title
;
Intramolecular Hydrogen-Bonded Tertiary Phosphines as
1,3,5-Triaza-7-phosphaadamantane (PTA) Analogues
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2633
_journal_page_last               2638
_journal_paper_doi               10.1021/ic801709z
_journal_volume                  48
_journal_year                    2009
_chemical_formula_moiety         'C25 H31 N3 P1 1+, P1 F6 1-'
_chemical_formula_sum            'C25 H31 F6 N3 P2'
_chemical_formula_weight         549.47
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.9476(5)
_cell_length_b                   15.8400(5)
_cell_length_c                   19.1365(6)
_cell_measurement_reflns_used    17860
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      2.27
_cell_volume                     5440.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            62276
_diffrn_reflns_theta_full        30.55
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.9678
_exptl_absorpt_correction_T_min  0.8980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2007/2, Sheldrick, G.M., (2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         8335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0377
_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)+(0.0589P)²+1.3791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                6759
_reflns_number_total             8335
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic801709z_si_002_3.cif
_cod_data_source_block           3a
_cod_database_code               4301660
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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 0.090508(17) 0.54355(2) 0.054547(15) 0.02791(8) Uani 1 1 d . . .
C1 C 0.19089(6) 0.54006(7) 0.07609(6) 0.0256(2) Uani 1 1 d . . .
H1C H 0.2119 0.4876 0.0561 0.031 Uiso 1 1 calc R . .
H1D H 0.2156 0.5881 0.0524 0.031 Uiso 1 1 calc R . .
N1 N 0.21099(5) 0.54328(6) 0.15219(5) 0.02307(17) Uani 1 1 d . . .
H1A H 0.1937(8) 0.5886(9) 0.1697(7) 0.028 Uiso 1 1 d . . .
H1B H 0.1869(8) 0.5034(9) 0.1743(7) 0.028 Uiso 1 1 d . . .
C2 C 0.29312(6) 0.53678(8) 0.16468(6) 0.0288(2) Uani 1 1 d . . .
H2A H 0.3190 0.5824 0.1390 0.035 Uiso 1 1 calc R . .
H2B H 0.3115 0.4821 0.1465 0.035 Uiso 1 1 calc R . .
C3 C 0.31118(6) 0.54349(7) 0.24132(6) 0.0278(2) Uani 1 1 d . . .
C4 C 0.31942(7) 0.47110(9) 0.28185(8) 0.0371(3) Uani 1 1 d . . .
H4 H 0.3147 0.4170 0.2610 0.045 Uiso 1 1 calc R . .
C5 C 0.33465(8) 0.47805(11) 0.35310(8) 0.0467(4) Uani 1 1 d . . .
H5 H 0.3407 0.4286 0.3806 0.056 Uiso 1 1 calc R . .
C6 C 0.34094(8) 0.55676(12) 0.38376(7) 0.0458(4) Uani 1 1 d . . .
H6 H 0.3502 0.5613 0.4325 0.055 Uiso 1 1 calc R . .
C7 C 0.33377(7) 0.62915(10) 0.34357(7) 0.0411(3) Uani 1 1 d . . .
H7 H 0.3388 0.6832 0.3646 0.049 Uiso 1 1 calc R . .
C8 C 0.31917(7) 0.62233(8) 0.27236(6) 0.0325(2) Uani 1 1 d . . .
H8 H 0.3146 0.6719 0.2448 0.039 Uiso 1 1 calc R . .
C9 C 0.06006(7) 0.63561(7) 0.10536(6) 0.0274(2) Uani 1 1 d . . .
H9A H 0.0858 0.6864 0.0873 0.033 Uiso 1 1 calc R . .
H9B H 0.0059 0.6437 0.0981 0.033 Uiso 1 1 calc R . .
N2 N 0.07461(5) 0.62871(5) 0.18097(4) 0.02254(17) Uani 1 1 d . . .
C10 C 0.05351(7) 0.46130(7) 0.11261(6) 0.0283(2) Uani 1 1 d . . .
H10A H -0.0012 0.4581 0.1065 0.034 Uiso 1 1 calc R . .
H10B H 0.0747 0.4061 0.0986 0.034 Uiso 1 1 calc R . .
N3 N 0.07016(5) 0.47604(5) 0.18716(5) 0.02325(17) Uani 1 1 d . . .
C11 C 0.03622(6) 0.55533(6) 0.21110(6) 0.02308(19) Uani 1 1 d . . .
H11A H -0.0169 0.5565 0.1973 0.028 Uiso 1 1 calc R . .
H11B H 0.0388 0.5583 0.2627 0.028 Uiso 1 1 calc R . .
C12 C 0.04817(7) 0.70709(7) 0.21493(6) 0.0275(2) Uani 1 1 d . . .
H12A H -0.0062 0.7125 0.2075 0.033 Uiso 1 1 calc R . .
H12B H 0.0725 0.7561 0.1924 0.033 Uiso 1 1 calc R . .
C13 C 0.06396(6) 0.70951(7) 0.29209(6) 0.0265(2) Uani 1 1 d . . .
C14 C 0.13659(7) 0.71775(10) 0.31638(7) 0.0422(3) Uani 1 1 d . . .
H14 H 0.1765 0.7222 0.2840 0.051 Uiso 1 1 calc R . .
C15 C 0.15112(9) 0.71957(13) 0.38756(8) 0.0563(5) Uani 1 1 d . . .
H15 H 0.2010 0.7243 0.4038 0.068 Uiso 1 1 calc R . .
C16 C 0.09302(9) 0.71448(11) 0.43508(8) 0.0493(4) Uani 1 1 d . . .
H16 H 0.1031 0.7160 0.4838 0.059 Uiso 1 1 calc R . .
C17 C 0.02075(8) 0.70729(10) 0.41170(7) 0.0397(3) Uani 1 1 d . . .
H17 H -0.0192 0.7046 0.4442 0.048 Uiso 1 1 calc R . .
C18 C 0.00644(7) 0.70400(8) 0.34038(6) 0.0306(2) Uani 1 1 d . . .
H18 H -0.0434 0.6979 0.3244 0.037 Uiso 1 1 calc R . .
C19 C 0.03950(7) 0.40424(7) 0.22787(6) 0.0312(2) Uani 1 1 d . . .
H19A H 0.0585 0.3509 0.2077 0.037 Uiso 1 1 calc R . .
H19B H -0.0154 0.4041 0.2230 0.037 Uiso 1 1 calc R . .
C20 C 0.05883(7) 0.40671(8) 0.30405(7) 0.0334(3) Uani 1 1 d . . .
C21 C 0.13149(9) 0.39078(13) 0.32552(9) 0.0584(5) Uani 1 1 d . . .
H21 H 0.1691 0.3809 0.2916 0.070 Uiso 1 1 calc R . .
C22 C 0.14942(12) 0.38926(19) 0.39568(11) 0.0860(8) Uani 1 1 d . . .
H22 H 0.1992 0.3781 0.4099 0.103 Uiso 1 1 calc R . .
C23 C 0.09466(14) 0.40401(18) 0.44545(10) 0.0836(8) Uani 1 1 d . . .
H23 H 0.1071 0.4036 0.4937 0.100 Uiso 1 1 calc R . .
C24 C 0.02208(13) 0.41930(15) 0.42493(9) 0.0667(5) Uani 1 1 d . . .
H24 H -0.0155 0.4292 0.4590 0.080 Uiso 1 1 calc R . .
C25 C 0.00428(9) 0.42020(10) 0.35430(8) 0.0448(3) Uani 1 1 d . . .
H25 H -0.0457 0.4301 0.3402 0.054 Uiso 1 1 calc R . .
P2 P 0.234263(18) 0.288271(19) 0.091384(16) 0.02953(8) Uani 1 1 d . . .
F1 F 0.30627(6) 0.34512(6) 0.08016(6) 0.0588(3) Uani 1 1 d . . .
F2 F 0.16252(5) 0.23108(6) 0.10411(5) 0.0500(2) Uani 1 1 d . . .
F3 F 0.18930(7) 0.34266(6) 0.03570(5) 0.0601(3) Uani 1 1 d . . .
F4 F 0.26113(5) 0.22579(5) 0.03087(4) 0.0460(2) Uani 1 1 d . . .
F5 F 0.27837(5) 0.23250(5) 0.14777(4) 0.04177(19) Uani 1 1 d . . .
F6 F 0.20776(5) 0.35131(5) 0.15242(4) 0.0438(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'
F F 0.0171 0.0103 '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
C9 P1 C10 97.78(5) . . ?
C9 P1 C1 101.28(5) . . ?
C10 P1 C1 101.32(5) . . ?
N1 C1 P1 116.70(7) . . ?
C2 N1 C1 112.90(9) . . ?
N1 C2 C3 111.26(9) . . ?
C8 C3 C4 119.40(12) . . ?
C8 C3 C2 120.11(10) . . ?
C4 C3 C2 120.49(11) . . ?
C3 C4 C5 120.03(14) . . ?
C6 C5 C4 120.12(13) . . ?
C5 C6 C7 120.18(13) . . ?
C6 C7 C8 119.76(14) . . ?
C3 C8 C7 120.48(12) . . ?
N2 C9 P1 114.09(7) . . ?
C11 N2 C9 111.15(9) . . ?
C11 N2 C12 109.95(8) . . ?
C9 N2 C12 108.18(8) . . ?
N3 C10 P1 113.53(7) . . ?
C11 N3 C10 110.65(9) . . ?
C11 N3 C19 109.74(9) . . ?
C10 N3 C19 108.12(9) . . ?
N2 C11 N3 111.07(8) . . ?
N2 C12 C13 113.08(9) . . ?
C18 C13 C14 118.72(11) . . ?
C18 C13 C12 120.78(11) . . ?
C14 C13 C12 120.50(11) . . ?
C15 C14 C13 120.44(13) . . ?
C16 C15 C14 120.11(14) . . ?
C17 C16 C15 120.03(13) . . ?
C16 C17 C18 119.75(13) . . ?
C13 C18 C17 120.93(12) . . ?
N3 C19 C20 113.87(9) . . ?
C25 C20 C21 118.98(14) . . ?
C25 C20 C19 120.94(12) . . ?
C21 C20 C19 119.98(13) . . ?
C22 C21 C20 120.61(17) . . ?
C21 C22 C23 119.9(2) . . ?
C24 C23 C22 120.12(18) . . ?
C23 C24 C25 119.68(18) . . ?
C20 C25 C24 120.66(16) . . ?
F1 P2 F3 90.87(6) . . ?
F1 P2 F2 178.94(6) . . ?
F3 P2 F2 90.02(6) . . ?
F1 P2 F4 90.43(5) . . ?
F3 P2 F4 90.17(5) . . ?
F2 P2 F4 90.14(5) . . ?
F1 P2 F5 90.10(6) . . ?
F3 P2 F5 179.03(6) . . ?
F2 P2 F5 89.02(5) . . ?
F4 P2 F5 89.86(5) . . ?
F1 P2 F6 89.25(5) . . ?
F3 P2 F6 90.01(5) . . ?
F2 P2 F6 90.17(5) . . ?
F4 P2 F6 179.63(6) . . ?
F5 P2 F6 89.96(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 C9 1.8359(12) . ?
P1 C10 1.8366(13) . ?
P1 C1 1.8490(12) . ?
C1 N1 1.5013(14) . ?
N1 C2 1.4968(14) . ?
C2 C3 1.5058(16) . ?
C3 C8 1.3904(17) . ?
C3 C4 1.3922(17) . ?
C4 C5 1.395(2) . ?
C5 C6 1.383(2) . ?
C6 C7 1.387(2) . ?
C7 C8 1.3918(17) . ?
C9 N2 1.4743(14) . ?
N2 C11 1.4691(13) . ?
N2 C12 1.4796(13) . ?
C10 N3 1.4762(14) . ?
N3 C11 1.4691(13) . ?
N3 C19 1.4842(14) . ?
C12 C13 1.5041(16) . ?
C13 C18 1.3883(16) . ?
C13 C14 1.3901(17) . ?
C14 C15 1.387(2) . ?
C15 C16 1.386(2) . ?
C16 C17 1.377(2) . ?
C17 C18 1.3898(18) . ?
C19 C20 1.4991(18) . ?
C20 C25 1.389(2) . ?
C20 C21 1.390(2) . ?
C21 C22 1.381(2) . ?
C22 C23 1.388(3) . ?
C23 C24 1.382(3) . ?
C24 C25 1.389(2) . ?
P2 F1 1.5898(9) . ?
P2 F3 1.5903(9) . ?
P2 F2 1.5930(9) . ?
P2 F4 1.5977(8) . ?
P2 F5 1.6036(8) . ?
P2 F6 1.6086(8) . ?
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
N1 H1A F5 0.850(15) 2.372(15) 3.0045(13) 131.6(12) 8_665
N1 H1B N3 0.875(15) 2.154(15) 2.8234(13) 132.9(12) .
N1 H1B F6 0.875(15) 2.473(15) 3.0414(13) 123.2(12) .
N1 H1A N2 0.850(15) 2.241(15) 2.8506(13) 128.7(12) .
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
C9 P1 C1 N1 50.51(9) . . . . ?
C10 P1 C1 N1 -49.91(9) . . . . ?
P1 C1 N1 C2 177.78(8) . . . . ?
C1 N1 C2 C3 177.90(9) . . . . ?
N1 C2 C3 C8 -84.75(13) . . . . ?
N1 C2 C3 C4 94.74(13) . . . . ?
C8 C3 C4 C5 0.79(18) . . . . ?
C2 C3 C4 C5 -178.70(11) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C7 -1.4(2) . . . . ?
C5 C6 C7 C8 0.9(2) . . . . ?
C4 C3 C8 C7 -1.32(18) . . . . ?
C2 C3 C8 C7 178.18(11) . . . . ?
C6 C7 C8 C3 0.48(19) . . . . ?
C10 P1 C9 N2 45.18(9) . . . . ?
C1 P1 C9 N2 -58.08(9) . . . . ?
P1 C9 N2 C11 -59.80(11) . . . . ?
P1 C9 N2 C12 179.40(8) . . . . ?
C9 P1 C10 N3 -45.97(9) . . . . ?
C1 P1 C10 N3 57.25(9) . . . . ?
P1 C10 N3 C11 61.55(10) . . . . ?
P1 C10 N3 C19 -178.25(8) . . . . ?
C9 N2 C11 N3 69.91(11) . . . . ?
C12 N2 C11 N3 -170.33(9) . . . . ?
C10 N3 C11 N2 -70.88(11) . . . . ?
C19 N3 C11 N2 169.89(9) . . . . ?
C11 N2 C12 C13 61.66(12) . . . . ?
C9 N2 C12 C13 -176.80(9) . . . . ?
N2 C12 C13 C18 -110.56(12) . . . . ?
N2 C12 C13 C14 69.77(15) . . . . ?
C18 C13 C14 C15 0.6(2) . . . . ?
C12 C13 C14 C15 -179.70(14) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C16 C17 C18 0.9(2) . . . . ?
C14 C13 C18 C17 0.50(18) . . . . ?
C12 C13 C18 C17 -179.18(11) . . . . ?
C16 C17 C18 C13 -1.2(2) . . . . ?
C11 N3 C19 C20 -64.82(13) . . . . ?
C10 N3 C19 C20 174.41(10) . . . . ?
N3 C19 C20 C25 112.39(14) . . . . ?
N3 C19 C20 C21 -71.16(17) . . . . ?
C25 C20 C21 C22 -0.7(3) . . . . ?
C19 C20 C21 C22 -177.20(19) . . . . ?
C20 C21 C22 C23 -0.2(4) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C22 C23 C24 C25 -0.3(4) . . . . ?
C21 C20 C25 C24 1.1(2) . . . . ?
C19 C20 C25 C24 177.60(15) . . . . ?
C23 C24 C25 C20 -0.7(3) . . . . ?
