#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/54/4065470.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_4065470
loop_
_publ_author_name
'Cui, Huiling'
'Goddard, Richard'
'Pörschke, Klaus-Richard'
_publ_section_title
;
 Synthesis and Coordination Chemistry ofN,N-Diallylbispidine
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              6241
_journal_paper_doi               10.1021/om200824c
_journal_volume                  30
_journal_year                    2011
_chemical_compound_source        tetrahydrofurane
_chemical_formula_moiety         'C13 H23 N2, F6 P'
_chemical_formula_sum            'C13 H23 F6 N2 P'
_chemical_formula_weight         352.30
_chemical_name_systematic
;
 3,7-Diallyl-3-diaza-7-diazonium-bicyclo[3.3.1]nonane(N,N'-Diallyl-bispidine)
 hexafluorophosphate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                CUI-CB-053-01
_audit_creation_date             2011-07-01
_cell_angle_alpha                90.00
_cell_angle_beta                 96.668(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3476(2)
_cell_length_b                   16.4450(10)
_cell_length_c                   11.7254(6)
_cell_measurement_reflns_used    54433
_cell_measurement_temperature    100
_cell_measurement_theta_max      34.9993
_cell_measurement_theta_min      2.7526
_cell_volume                     1598.73(13)
_computing_cell_refinement       'DENZO (Bruker AXS, 2006)'
_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'DENZO (Bruker AXS, 2006)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            49126
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         35.01
_diffrn_reflns_theta_min         2.75
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.14007
_exptl_absorpt_correction_T_min  0.04201
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.448
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.350
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         7036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0328
_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)+(0.0389P)²+0.3853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                6009
_reflns_number_total             7036
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om200824c_si_002.cif
_cod_data_source_block           9
_cod_original_sg_symbol_Hall     '-p 2yn'
_cod_original_sg_symbol_H-M      'p 21/n'
_cod_database_code               4065470
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
P1 P 0.23296(2) 0.144315(12) 0.255263(17) 0.01567(5) Uani 1 1 d .
F1 F 0.14365(7) 0.18011(4) 0.35923(5) 0.02646(11) Uani 1 1 d .
F2 F 0.10233(7) 0.19006(4) 0.16585(5) 0.03021(13) Uani 1 1 d .
F3 F 0.34611(7) 0.22358(3) 0.26046(5) 0.02659(11) Uani 1 1 d .
F4 F 0.32126(9) 0.10984(4) 0.15151(6) 0.03252(14) Uani 1 1 d .
F5 F 0.36147(7) 0.09943(4) 0.34573(6) 0.03189(13) Uani 1 1 d .
F6 F 0.11861(7) 0.06564(3) 0.25029(5) 0.02522(11) Uani 1 1 d .
N1 N 0.78374(8) 0.22670(4) 0.30935(5) 0.01575(11) Uani 1 1 d .
H1 H 0.8861(15) 0.2404(7) 0.3188(10) 0.020(3) Uiso 1 1 d .
N2 N 0.97844(8) 0.35965(4) 0.29793(5) 0.01575(11) Uani 1 1 d .
C1 C 0.70726(10) 0.27599(5) 0.39722(7) 0.01962(14) Uani 1 1 d .
H1B H 0.7631 0.2652 0.4730 0.024 Uiso 1 1 calc R
H1A H 0.5957 0.2594 0.3972 0.024 Uiso 1 1 calc R
C2 C 0.71374(10) 0.36711(5) 0.37218(8) 0.02156(14) Uani 1 1 d .
H2 H 0.6557 0.3959 0.4280 0.026 Uiso 1 1 calc R
C3 C 0.88675(10) 0.40002(5) 0.38208(7) 0.02042(14) Uani 1 1 d .
H3B H 0.8845 0.4582 0.3684 0.024 Uiso 1 1 calc R
H3A H 0.9395 0.3905 0.4591 0.024 Uiso 1 1 calc R
C4 C 0.89970(10) 0.37255(5) 0.18031(7) 0.01949(13) Uani 1 1 d .
H4A H 0.9603 0.3446 0.1264 0.023 Uiso 1 1 calc R
H4B H 0.8994 0.4301 0.1624 0.023 Uiso 1 1 calc R
C5 C 0.72601(10) 0.34078(5) 0.16721(7) 0.02079(14) Uani 1 1 d .
H5 H 0.6767 0.3523 0.0889 0.025 Uiso 1 1 calc R
C6 C 0.71907(9) 0.24916(5) 0.18761(6) 0.01878(13) Uani 1 1 d .
H6A H 0.6082 0.2308 0.1721 0.023 Uiso 1 1 calc R
H6B H 0.7817 0.2215 0.1347 0.023 Uiso 1 1 calc R
C7 C 0.62888(10) 0.38464(6) 0.25165(9) 0.02561(16) Uani 1 1 d .
H7A H 0.5189 0.3645 0.2443 0.031 Uiso 1 1 calc R
H7B H 0.6264 0.4427 0.2368 0.031 Uiso 1 1 calc R
C8 C 0.76376(10) 0.13638(5) 0.32500(7) 0.01888(13) Uani 1 1 d .
H8A H 0.6497 0.1234 0.3135 0.023 Uiso 1 1 calc R
H8B H 0.8151 0.1082 0.2663 0.023 Uiso 1 1 calc R
C9 C 0.83300(11) 0.10530(5) 0.44016(8) 0.02372(15) Uani 1 1 d .
H9 H 0.9416 0.1146 0.4642 0.028 Uiso 1 1 calc R
C10 C 0.74627(13) 0.06508(6) 0.50948(8) 0.02675(17) Uani 1 1 d .
H10A H 0.6320(19) 0.0588(9) 0.4902(12) 0.037(4) Uiso 1 1 d .
H10B H 0.7947(19) 0.0424(9) 0.5821(13) 0.038(4) Uiso 1 1 d .
C11 C 1.14553(9) 0.39008(5) 0.30588(7) 0.01746(13) Uani 1 1 d .
H11B H 1.1434 0.4485 0.2944 0.021 Uiso 1 1 calc R
H11A H 1.1987 0.3660 0.2448 0.021 Uiso 1 1 calc R
C12 C 1.24154(10) 0.37140(5) 0.41881(7) 0.01841(13) Uani 1 1 d .
H12 H 1.2402 0.3184 0.4463 0.022 Uiso 1 1 calc R
C13 C 1.32856(10) 0.42632(5) 0.48191(7) 0.02226(15) Uani 1 1 d .
H13A H 1.3288(18) 0.4821(9) 0.4552(12) 0.034(4) Uiso 1 1 d .
H13B H 1.3950(17) 0.4130(8) 0.5519(12) 0.027(3) Uiso 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.2000
0.00 0.00 1.00 0.2200
0.00 -1.00 0.00 0.1900
0.00 1.00 0.00 0.1600
1.00 0.00 0.00 0.2110
-1.00 0.00 0.00 0.2270
4.00 0.00 -3.00 0.2190
-1.00 0.00 1.00 0.2500
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
F4 P1 F5 90.46(4) y
F4 P1 F6 90.65(3) y
F5 P1 F6 90.13(3) y
F4 P1 F3 89.75(3) y
F5 P1 F3 90.19(3) y
F6 P1 F3 179.49(3) y
F4 P1 F2 90.43(4) y
F5 P1 F2 179.11(4) y
F6 P1 F2 89.89(3) y
F3 P1 F2 89.79(3) y
F4 P1 F1 179.33(3) y
F5 P1 F1 90.03(4) y
F6 P1 F1 89.80(3) y
F3 P1 F1 89.80(3) y
F2 P1 F1 89.09(4) y
C8 N1 C1 112.59(6) y
C8 N1 C6 108.85(6) y
C1 N1 C6 112.34(6) y
C8 N1 H1 111.0(8) y
C1 N1 H1 104.9(8) y
C6 N1 H1 107.0(8) y
C4 N2 C11 109.05(6) y
C4 N2 C3 110.60(6) y
C11 N2 C3 111.44(6) y
N1 C1 C2 111.59(6) y
N1 C1 H1B 109.3 n
C2 C1 H1B 109.3 n
N1 C1 H1A 109.3 n
C2 C1 H1A 109.3 n
H1B C1 H1A 108.0 n
C1 C2 C7 109.79(7) y
C1 C2 C3 112.65(7) y
C7 C2 C3 109.48(7) y
C1 C2 H2 108.3 n
C7 C2 H2 108.3 n
C3 C2 H2 108.3 n
N2 C3 C2 110.35(6) y
N2 C3 H3B 109.6 n
C2 C3 H3B 109.6 n
N2 C3 H3A 109.6 n
C2 C3 H3A 109.6 n
H3B C3 H3A 108.1 n
N2 C4 C5 111.04(6) y
N2 C4 H4A 109.4 n
C5 C4 H4A 109.4 n
N2 C4 H4B 109.4 n
C5 C4 H4B 109.4 n
H4A C4 H4B 108.0 n
C6 C5 C7 109.32(7) y
C6 C5 C4 111.91(7) y
C7 C5 C4 109.91(7) y
C6 C5 H5 108.5 n
C7 C5 H5 108.5 n
C4 C5 H5 108.5 n
N1 C6 C5 111.90(6) y
N1 C6 H6A 109.2 n
C5 C6 H6A 109.2 n
N1 C6 H6B 109.2 n
C5 C6 H6B 109.2 n
H6A C6 H6B 107.9 n
C5 C7 C2 106.55(7) y
C5 C7 H7A 110.4 n
C2 C7 H7A 110.4 n
C5 C7 H7B 110.4 n
C2 C7 H7B 110.4 n
H7A C7 H7B 108.6 n
C9 C8 N1 114.19(7) y
C9 C8 H8A 108.7 n
N1 C8 H8A 108.7 n
C9 C8 H8B 108.7 n
N1 C8 H8B 108.7 n
H8A C8 H8B 107.6 n
C10 C9 C8 122.85(8) y
C10 C9 H9 118.6 n
C8 C9 H9 118.6 n
C9 C10 H10A 120.5(9) y
C9 C10 H10B 121.8(9) y
H10A C10 H10B 117.7(12) y
N2 C11 C12 113.03(6) y
N2 C11 H11B 109.0 n
C12 C11 H11B 109.0 n
N2 C11 H11A 109.0 n
C12 C11 H11A 109.0 n
H11B C11 H11A 107.8 n
C13 C12 C11 123.68(7) y
C13 C12 H12 118.2 n
C11 C12 H12 118.2 n
C12 C13 H13A 119.0(9) y
C12 C13 H13B 123.0(8) y
H13A C13 H13B 118.0(12) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P1 F4 1.5978(6) y
P1 F5 1.5989(6) y
P1 F6 1.6049(6) y
P1 F3 1.6068(6) y
P1 F2 1.6090(6) y
P1 F1 1.6123(6) y
N1 C8 1.5081(10) y
N1 C1 1.5096(10) y
N1 C6 1.5121(10) y
N1 H1 0.878(13) y
N2 C4 1.4726(10) y
N2 C11 1.4747(10) y
N2 C3 1.4749(10) y
C1 C2 1.5291(12) y
C1 H1B 0.9700 n
C1 H1A 0.9700 n
C2 C7 1.5329(13) y
C2 C3 1.5340(12) y
C2 H2 0.9800 n
C3 H3B 0.9700 n
C3 H3A 0.9700 n
C4 C5 1.5320(12) y
C4 H4A 0.9700 n
C4 H4B 0.9700 n
C5 C6 1.5277(12) y
C5 C7 1.5311(13) y
C5 H5 0.9800 n
C6 H6A 0.9700 n
C6 H6B 0.9700 n
C7 H7A 0.9700 n
C7 H7B 0.9700 n
C8 C9 1.4958(12) y
C8 H8A 0.9700 n
C8 H8B 0.9700 n
C9 C10 1.3263(12) y
C9 H9 0.9300 n
C10 H10A 0.961(15) y
C10 H10B 0.973(15) y
C11 C12 1.4979(11) y
C11 H11B 0.9700 n
C11 H11A 0.9700 n
C12 C13 1.3289(11) y
C12 H12 0.9300 n
C13 H13A 0.970(14) y
C13 H13B 0.961(14) y
