#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:52:30 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179601 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/65/4506531.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_4506531
loop_
_publ_author_name
'Peuronen, Anssi'
'Valkonen, Arto'
'Kortelainen, Minna'
'Rissanen, Kari'
'Lahtinen, Manu'
_publ_section_title
;
 Halogen Bonding-Based “Catch and Release”: Reversible
 Solid-State Entrapment of Elemental Iodine with Monoalkylated DABCO Salts
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4157
_journal_paper_doi               10.1021/cg300669t
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C16 H33 N2, F6 P'
_chemical_formula_sum            'C16 H33 F6 N2 P'
_chemical_formula_weight         398.41
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m 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            4
_cell_length_a                   7.9020(3)
_cell_length_b                   6.9120(4)
_cell_length_c                   37.3530(19)
_cell_measurement_reflns_used    2510
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.407
_cell_volume                     2040.17(18)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       Collect
_computing_data_reduction        DENZO-SMN
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type
'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            8028
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.09
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008/1 (Bruker,2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1889
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0730
_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)+(0.0749P)²+2.2760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1982
_refine_ls_wR_factor_ref         0.2375
_reflns_number_gt                1204
_reflns_number_total             1889
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg300669t_si_002.cif
_cod_data_source_block           4PF6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               4506531
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -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
P1 P 0.3863(2) -0.2500 0.66758(5) 0.0792(7) Uani 1 2 d S
N2 N -0.1216(5) 0.2500 0.65661(10) 0.0464(10) Uani 1 2 d S
F1 F 0.3519(5) -0.1057(4) 0.69568(11) 0.1360(14) Uani 1 1 d .
N1 N -0.2277(6) 0.2500 0.72274(11) 0.0618(12) Uani 1 2 d S
F3 F 0.1627(5) -0.2500 0.65852(14) 0.1156(16) Uani 1 2 d S
F2 F 0.4169(5) -0.1077(4) 0.63822(11) 0.1348(14) Uani 1 1 d .
C5 C -0.0653(7) 0.2500 0.61798(13) 0.0563(13) Uani 1 2 d S
H5A H -0.1135 0.3630 0.6064 0.068 Uiso 0.50 1 calc PR
H5B H -0.1135 0.1370 0.6064 0.068 Uiso 0.50 1 calc PR
C12 C 0.9367(8) 0.2500 0.46814(15) 0.0752(17) Uani 1 2 d S
H12A H 0.9855 0.3632 0.4795 0.090 Uiso 0.50 1 calc PR
H12B H 0.9855 0.1368 0.4795 0.090 Uiso 0.50 1 calc PR
C9 C 0.4543(8) 0.2500 0.52322(15) 0.0700(16) Uani 1 2 d S
H9A H 0.4049 0.3632 0.5120 0.084 Uiso 0.50 1 calc PR
H9B H 0.4049 0.1368 0.5120 0.084 Uiso 0.50 1 calc PR
C4 C -0.0495(6) 0.0945(5) 0.67574(11) 0.0736(12) Uani 1 1 d .
H4A H 0.0729 0.1043 0.6753 0.088 Uiso 1 1 calc R
H4B H -0.0816 -0.0272 0.6647 0.088 Uiso 1 1 calc R
C1 C -0.3954(7) 0.2500 0.69860(15) 0.0700(16) Uani 1 2 d S
H1A H -0.4631 0.1360 0.7035 0.084 Uiso 0.50 1 calc PR
H1B H -0.4631 0.3640 0.7035 0.084 Uiso 0.50 1 calc PR
C6 C 0.1497(7) 0.2500 0.61004(15) 0.0650(15) Uani 1 2 d S
H6A H 0.1997 0.3634 0.6211 0.078 Uiso 0.50 1 calc PR
H6B H 0.1997 0.1366 0.6211 0.078 Uiso 0.50 1 calc PR
C8 C 0.4065(7) 0.2500 0.56200(15) 0.0690(16) Uani 1 2 d S
H8A H 0.4560 0.3632 0.5732 0.083 Uiso 0.50 1 calc PR
H8B H 0.4560 0.1368 0.5732 0.083 Uiso 0.50 1 calc PR
F4 F 0.6101(5) -0.2500 0.67481(15) 0.1240(18) Uani 1 2 d S
C11 C 0.7204(8) 0.2500 0.47602(15) 0.0745(17) Uani 1 2 d S
H11A H 0.6716 0.3632 0.4647 0.089 Uiso 0.50 1 calc PR
H11B H 0.6716 0.1368 0.4647 0.089 Uiso 0.50 1 calc PR
C7 C 0.1906(7) 0.2500 0.57042(15) 0.0671(15) Uani 1 2 d S
H7A H 0.1403 0.3634 0.5594 0.080 Uiso 0.50 1 calc PR
H7B H 0.1403 0.1366 0.5594 0.080 Uiso 0.50 1 calc PR
C10 C 0.6703(8) 0.2500 0.51483(16) 0.0717(16) Uani 1 2 d S
H10A H 0.7194 0.3631 0.5261 0.086 Uiso 0.50 1 calc PR
H10B H 0.7194 0.1369 0.5261 0.086 Uiso 0.50 1 calc PR
C3 C -0.1129(6) 0.1010(6) 0.71441(12) 0.0784(13) Uani 1 1 d .
H3A H -0.1666 -0.0219 0.7198 0.094 Uiso 1 1 calc R
H3B H -0.0157 0.1133 0.7301 0.094 Uiso 1 1 calc R
C2 C -0.3369(7) 0.2500 0.65986(15) 0.0631(14) Uani 1 2 d S
H2A H -0.3815 0.3635 0.6479 0.076 Uiso 0.50 1 calc PR
H2B H -0.3815 0.1365 0.6479 0.076 Uiso 0.50 1 calc PR
C13 C 0.9867(9) 0.2500 0.42929(17) 0.086(2) Uani 1 2 d S
H13A H 0.9380 0.3632 0.4179 0.104 Uiso 0.50 1 calc PR
H13B H 0.9380 0.1368 0.4179 0.104 Uiso 0.50 1 calc PR
C14 C 1.2017(11) 0.2500 0.4216(2) 0.111(3) Uani 1 2 d S
H14A H 1.2225 0.2500 0.3962 0.167 Uiso 1 2 calc SR
H14B H 1.2512 0.1366 0.4321 0.167 Uiso 0.50 1 calc PR
H14C H 1.2512 0.3634 0.4321 0.167 Uiso 0.50 1 calc PR
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
F1 P1 F1 85.2(3) 8 .
F1 P1 F2 177.9(2) 8 .
F1 P1 F2 96.2(2) . .
F1 P1 F2 96.2(2) 8 8
F1 P1 F2 177.9(2) . 8
F2 P1 F2 82.4(3) . 8
F1 P1 F4 94.3(2) 8 .
F1 P1 F4 94.3(2) . .
F2 P1 F4 87.2(2) . .
F2 P1 F4 87.2(2) 8 .
F1 P1 F3 87.3(2) 8 .
F1 P1 F3 87.3(2) . .
F2 P1 F3 91.2(2) . .
F2 P1 F3 91.2(2) 8 .
F4 P1 F3 177.8(3) . .
C4 N2 C4 99.3(4) 8_565 .
C4 N2 C5 111.4(3) 8_565 .
C4 N2 C5 111.4(3) . .
C4 N2 C2 111.5(3) 8_565 .
C4 N2 C2 111.5(3) . .
C5 N2 C2 111.2(3) . .
C3 N1 C3 94.1(5) 8_565 .
C3 N1 C1 114.1(3) 8_565 .
C3 N1 C1 114.1(3) . .
N2 C5 C6 117.0(4) . .
N2 C5 H5A 108.0 . .
C6 C5 H5A 108.0 . .
N2 C5 H5B 108.0 . .
C6 C5 H5B 108.0 . .
H5A C5 H5B 107.3 . .
C13 C12 C11 115.0(5) . .
C13 C12 H12A 108.5 . .
C11 C12 H12A 108.5 . .
C13 C12 H12B 108.5 . .
C11 C12 H12B 108.5 . .
H12A C12 H12B 107.5 . .
C8 C9 C10 115.0(5) . .
C8 C9 H9A 108.5 . .
C10 C9 H9A 108.5 . .
C8 C9 H9B 108.5 . .
C10 C9 H9B 108.5 . .
H9A C9 H9B 107.5 . .
N2 C4 C3 108.9(3) . .
N2 C4 H4A 109.9 . .
C3 C4 H4A 109.9 . .
N2 C4 H4B 109.9 . .
C3 C4 H4B 109.9 . .
H4A C4 H4B 108.3 . .
C2 C1 N1 106.5(4) . .
C2 C1 H1A 110.4 . .
N1 C1 H1A 110.4 . .
C2 C1 H1B 110.4 . .
N1 C1 H1B 110.4 . .
H1A C1 H1B 108.6 . .
C7 C6 C5 112.2(4) . .
C7 C6 H6A 109.2 . .
C5 C6 H6A 109.2 . .
C7 C6 H6B 109.2 . .
C5 C6 H6B 109.2 . .
H6A C6 H6B 107.9 . .
C9 C8 C7 115.0(5) . .
C9 C8 H8A 108.5 . .
C7 C8 H8A 108.5 . .
C9 C8 H8B 108.5 . .
C7 C8 H8B 108.5 . .
H8A C8 H8B 107.5 . .
C10 C11 C12 115.0(5) . .
C10 C11 H11A 108.5 . .
C12 C11 H11A 108.5 . .
C10 C11 H11B 108.5 . .
C12 C11 H11B 108.5 . .
H11A C11 H11B 107.5 . .
C6 C7 C8 112.7(4) . .
C6 C7 H7A 109.0 . .
C8 C7 H7A 109.0 . .
C6 C7 H7B 109.0 . .
C8 C7 H7B 109.0 . .
H7A C7 H7B 107.8 . .
C11 C10 C9 115.7(5) . .
C11 C10 H10A 108.4 . .
C9 C10 H10A 108.4 . .
C11 C10 H10B 108.4 . .
C9 C10 H10B 108.4 . .
H10A C10 H10B 107.4 . .
N1 C3 C4 116.2(3) . .
N1 C3 H3A 108.2 . .
C4 C3 H3A 108.2 . .
N1 C3 H3B 108.2 . .
C4 C3 H3B 108.2 . .
H3A C3 H3B 107.4 . .
C1 C2 N2 111.8(4) . .
C1 C2 H2A 109.3 . .
N2 C2 H2A 109.3 . .
C1 C2 H2B 109.3 . .
N2 C2 H2B 109.3 . .
H2A C2 H2B 107.9 . .
C12 C13 C14 114.9(5) . .
C12 C13 H13A 108.6 . .
C14 C13 H13A 108.6 . .
C12 C13 H13B 108.6 . .
C14 C13 H13B 108.6 . .
H13A C13 H13B 107.5 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 F1 1.473(3) 8
P1 F1 1.473(3) .
P1 F2 1.493(3) .
P1 F2 1.493(3) 8
P1 F4 1.788(4) .
P1 F3 1.799(4) .
N2 C4 1.411(4) 8_565
N2 C4 1.411(4) .
N2 C5 1.510(6) .
N2 C2 1.706(6) .
N1 C3 1.408(5) 8_565
N1 C3 1.408(5) .
N1 C1 1.602(7) .
C5 C6 1.725(7) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C12 C13 1.504(8) .
C12 C11 1.735(8) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C9 C8 1.497(7) .
C9 C10 1.736(8) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C4 C3 1.530(6) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C1 C2 1.519(7) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C6 C7 1.515(8) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C8 C7 1.735(7) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C11 C10 1.503(8) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C13 C14 1.723(9) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
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
C4 N2 C5 C6 54.9(3) 8_565
C4 N2 C5 C6 -54.9(3) .
C2 N2 C5 C6 180.000(3) .
C4 N2 C4 C3 63.2(5) 8_565
C5 N2 C4 C3 -179.3(4) .
C2 N2 C4 C3 -54.4(4) .
C3 N1 C1 C2 53.3(3) 8_565
C3 N1 C1 C2 -53.3(3) .
N2 C5 C6 C7 180.000(3) .
C10 C9 C8 C7 180.000(3) .
C13 C12 C11 C10 180.000(3) .
C5 C6 C7 C8 180.000(3) .
C9 C8 C7 C6 180.000(3) .
C12 C11 C10 C9 180.000(3) .
C8 C9 C10 C11 180.000(3) .
C3 N1 C3 C4 -61.3(6) 8_565
C1 N1 C3 C4 57.4(5) .
N2 C4 C3 N1 1.4(6) .
N1 C1 C2 N2 0.000(3) .
C4 N2 C2 C1 -55.0(3) 8_565
C4 N2 C2 C1 55.0(3) .
C5 N2 C2 C1 180.000(3) .
C11 C12 C13 C14 180.000(3) .
