#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:18:03 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179054 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/16/4301658.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_4301658
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 H28 F3 N3 P 1+, Cl 1-'
_chemical_formula_sum            'C25 H28 Cl F3 N3 P'
_chemical_formula_weight         493.92
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           40
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'A 2 -2a'
_symmetry_space_group_name_H-M   'A m a 2'
_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            4
_cell_length_a                   13.7194(15)
_cell_length_b                   18.513(2)
_cell_length_c                   9.5476(10)
_cell_measurement_reflns_used    8376
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.92
_cell_measurement_theta_min      2.20
_cell_volume                     2425.0(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_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 1.000
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'Bruker SMART 1000 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  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10554
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.97
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.257
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.257
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0546
_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)+(0.0000P)²+10.4569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1281
_reflns_number_gt                2902
_reflns_number_total             2932
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic801709z_si_002_1.cif
_cod_data_source_block           1b
_cod_database_code               4301658
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y, z'
'-x+1/2, y, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-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
P1 P 0.7500 -0.04821(6) 0.65910(13) 0.0211(2) Uani 1 2 d S . .
C1 C 0.7500 -0.0511(2) 0.4664(5) 0.0219(10) Uani 1 2 d S . .
H1C H 0.8081 -0.0785 0.4355 0.026 Uiso 0.50 1 calc PR . .
H1D H 0.6919 -0.0785 0.4355 0.026 Uiso 0.50 1 calc PR . .
N1 N 0.7500 0.0208(2) 0.3925(5) 0.0382(13) Uani 1 2 d S . .
H1A H 0.6958 0.0465 0.4197 0.046 Uiso 0.50 1 calc PR . .
H1B H 0.8042 0.0465 0.4197 0.046 Uiso 0.50 1 calc PR . .
C2 C 0.7500 0.0138(3) 0.2384(5) 0.0252(11) Uani 1 2 d S . .
H2A H 0.6916 -0.0135 0.2084 0.030 Uiso 0.50 1 calc PR . .
H2B H 0.8084 -0.0135 0.2084 0.030 Uiso 0.50 1 calc PR . .
C3 C 0.7500 0.0872(2) 0.1686(5) 0.0210(9) Uani 1 2 d S . .
C4 C 0.8367(3) 0.12167(19) 0.1368(4) 0.0265(7) Uani 1 1 d . . .
H4 H 0.8966 0.0983 0.1574 0.032 Uiso 1 1 calc R . .
C5 C 0.8380(3) 0.1897(2) 0.0753(4) 0.0295(8) Uani 1 1 d . . .
H5 H 0.8976 0.2136 0.0544 0.035 Uiso 1 1 calc R . .
C6 C 0.7500 0.2208(3) 0.0462(5) 0.0277(11) Uani 1 2 d S . .
F1 F 0.7500 0.28774(17) -0.0154(4) 0.0410(9) Uani 1 2 d S . .
C7 C 0.8527(2) 0.01388(16) 0.6932(4) 0.0226(7) Uani 1 1 d . . .
H7A H 0.8638 0.0166 0.7955 0.027 Uiso 1 1 calc R . .
H7B H 0.9124 -0.0063 0.6500 0.027 Uiso 1 1 calc R . .
N2 N 0.8371(2) 0.08776(14) 0.6389(3) 0.0227(6) Uani 1 1 d . . .
C8 C 0.7500 0.1189(2) 0.7041(5) 0.0193(9) Uani 1 2 d S . .
H8A H 0.7500 0.1084 0.8058 0.023 Uiso 1 2 calc SR . .
H8B H 0.7500 0.1720 0.6916 0.023 Uiso 1 2 calc SR . .
C9 C 0.9242(2) 0.13211(18) 0.6678(5) 0.0330(9) Uani 1 1 d . . .
H9A H 0.9816 0.1098 0.6221 0.040 Uiso 1 1 calc R . .
H9B H 0.9364 0.1331 0.7700 0.040 Uiso 1 1 calc R . .
C10 C 0.9122(2) 0.20820(18) 0.6151(4) 0.0256(8) Uani 1 1 d . . .
C11 C 0.9183(2) 0.2662(2) 0.7075(4) 0.0263(7) Uani 1 1 d . . .
H11 H 0.9300 0.2571 0.8040 0.032 Uiso 1 1 calc R . .
C12 C 0.9077(3) 0.33742(18) 0.6615(4) 0.0282(7) Uani 1 1 d . . .
H12 H 0.9131 0.3770 0.7244 0.034 Uiso 1 1 calc R . .
C13 C 0.8891(3) 0.3477(2) 0.5228(4) 0.0333(9) Uani 1 1 d . . .
F2 F 0.8781(2) 0.41719(12) 0.4756(3) 0.0495(7) Uani 1 1 d . . .
C14 C 0.8815(3) 0.2929(3) 0.4271(4) 0.0388(10) Uani 1 1 d . . .
H14 H 0.8687 0.3026 0.3311 0.047 Uiso 1 1 calc R . .
C15 C 0.8933(3) 0.2225(2) 0.4756(4) 0.0314(8) Uani 1 1 d . . .
H15 H 0.8883 0.1834 0.4114 0.038 Uiso 1 1 calc R . .
Cl1 Cl 1.0000 0.5000 0.87079(15) 0.0381(3) Uani 1 2 d S . .
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'
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
C1 P1 C7 101.21(15) . . ?
C1 P1 C7 101.21(15) . 4_655 ?
C7 P1 C7 99.4(2) . 4_655 ?
N1 C1 P1 116.2(3) . . ?
C2 N1 C1 112.9(4) . . ?
N1 C2 C3 111.2(4) . . ?
C4 C3 C4 118.5(4) . 4_655 ?
C4 C3 C2 120.7(2) . . ?
C4 C3 C2 120.7(2) 4_655 . ?
C3 C4 C5 121.5(4) . . ?
C6 C5 C4 117.1(4) . . ?
C5 C6 C5 124.2(5) 4_655 . ?
C5 C6 F1 117.9(2) 4_655 . ?
C5 C6 F1 117.9(2) . . ?
N2 C7 P1 113.8(2) . . ?
C8 N2 C9 111.2(3) . . ?
C8 N2 C7 109.4(3) . . ?
C9 N2 C7 109.4(3) . . ?
N2 C8 N2 109.2(4) 4_655 . ?
N2 C9 C10 111.6(3) . . ?
C15 C10 C11 118.3(3) . . ?
C15 C10 C9 121.4(4) . . ?
C11 C10 C9 120.2(4) . . ?
C10 C11 C12 121.5(4) . . ?
C13 C12 C11 117.1(4) . . ?
C12 C13 C14 124.1(4) . . ?
C12 C13 F2 118.1(4) . . ?
C14 C13 F2 117.9(4) . . ?
C13 C14 C15 117.6(4) . . ?
C10 C15 C14 121.4(4) . . ?
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 1.841(5) . ?
P1 C7 1.847(3) . ?
P1 C7 1.847(3) 4_655 ?
C1 N1 1.506(6) . ?
N1 C2 1.477(6) . ?
C2 C3 1.512(7) . ?
C3 C4 1.384(4) . ?
C3 C4 1.384(4) 4_655 ?
C4 C5 1.390(5) . ?
C5 C6 1.366(5) . ?
C6 C5 1.366(5) 4_655 ?
C6 F1 1.372(6) . ?
C7 N2 1.478(4) . ?
N2 C8 1.466(4) . ?
N2 C9 1.476(4) . ?
C8 N2 1.466(4) 4_655 ?
C9 C10 1.505(5) . ?
C10 C15 1.383(6) . ?
C10 C11 1.392(5) . ?
C11 C12 1.398(5) . ?
C12 C13 1.362(6) . ?
C13 C14 1.368(6) . ?
C13 F2 1.372(4) . ?
C14 C15 1.394(6) . ?
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 H1B N2 0.92 2.27 2.915(5) 126.4 .
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
C7 P1 C1 N1 -51.04(11) . . . . ?
C7 P1 C1 N1 51.04(11) 4_655 . . . ?
P1 C1 N1 C2 180.0 . . . . ?
C1 N1 C2 C3 180.0 . . . . ?
N1 C2 C3 C4 89.6(4) . . . . ?
N1 C2 C3 C4 -89.6(4) . . . 4_655 ?
C4 C3 C4 C5 0.5(7) 4_655 . . . ?
C2 C3 C4 C5 -178.6(4) . . . . ?
C3 C4 C5 C6 -0.7(6) . . . . ?
C4 C5 C6 C5 0.9(8) . . . 4_655 ?
C4 C5 C6 F1 -179.5(4) . . . . ?
C1 P1 C7 N2 63.4(3) . . . . ?
C7 P1 C7 N2 -40.1(3) 4_655 . . . ?
P1 C7 N2 C8 59.7(3) . . . . ?
P1 C7 N2 C9 -178.3(3) . . . . ?
C9 N2 C8 N2 162.5(3) . . . 4_655 ?
C7 N2 C8 N2 -76.6(4) . . . 4_655 ?
C8 N2 C9 C10 -58.7(5) . . . . ?
C7 N2 C9 C10 -179.7(3) . . . . ?
N2 C9 C10 C15 -58.2(5) . . . . ?
N2 C9 C10 C11 120.8(4) . . . . ?
C15 C10 C11 C12 -1.2(5) . . . . ?
C9 C10 C11 C12 179.8(3) . . . . ?
C10 C11 C12 C13 1.2(5) . . . . ?
C11 C12 C13 C14 -0.7(6) . . . . ?
C11 C12 C13 F2 179.8(4) . . . . ?
C12 C13 C14 C15 0.2(7) . . . . ?
F2 C13 C14 C15 179.7(4) . . . . ?
C11 C10 C15 C14 0.6(6) . . . . ?
C9 C10 C15 C14 179.6(4) . . . . ?
C13 C14 C15 C10 -0.1(6) . . . . ?
