#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/67/1506711.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_1506711
loop_
_publ_author_name
'Loeb, Stephen J.'
'Tiburcio, Jorge'
'Vella, Sarah J.'
_publ_contact_author
;
 Stephen J. Loeb
 Department of Chemistry and Biochemistry
 University of Windsor
 Windsor, Ontario, Canada
 N9B 3P4
;
_publ_section_title
;
 [2]pseudorotaxane formation with N-benzylanilinium axles and 24-crown-8
 ether wheels.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              4923
_journal_page_last               4926
_journal_paper_doi               10.1021/ol051786e
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C16 H15 F6 N O4 S'
_chemical_formula_weight         431.35
_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                   17.1855(11)
_cell_length_b                   8.6653(6)
_cell_length_c                   24.9779(16)
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      1.5
_cell_volume                     3719.6(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL XPREP'
_computing_molecular_graphics    'Bruker SHELXTL XP'
_computing_publication_material  'Bruker SHELXTL XCIF'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'hemisphere scans'
_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  0.0787
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17634
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%
;
;
_diffrn_standards_number         50
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.464560
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas
;
;
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0885
_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+14.1817P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1656
_refine_ls_wR_factor_ref         0.1718
_reflns_number_gt                2111
_reflns_number_total             2426
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051786esi20050728_035806.cif
_cod_data_source_block           Axle
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1506711
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
O1 O 0.1867(3) 0.7192(6) 0.47131(18) 0.0734(14) Uani 1 1 d .
N1 N 0.1355(2) 0.7058(5) 0.25038(19) 0.0476(12) Uani 1 1 d .
H1A H 0.1307 0.6046 0.2398 0.057 Uiso 1 1 calc R
H1E H 0.1773 0.7476 0.2325 0.057 Uiso 1 1 calc R
F1 F -0.0513(4) 0.8635(5) -0.00408(18) 0.124(2) Uani 1 1 d .
F2 F -0.0925(3) 0.6394(6) 0.00778(18) 0.1041(17) Uani 1 1 d .
F3 F 0.0219(3) 0.6733(7) -0.01775(18) 0.1061(17) Uani 1 1 d .
C1 C 0.2250(4) 0.8445(9) 0.4960(3) 0.083(2) Uani 1 1 d .
H1B H 0.2292 0.8253 0.5346 0.124 Uiso 1 1 calc R
H1C H 0.1952 0.9393 0.4899 0.124 Uiso 1 1 calc R
H1D H 0.2772 0.8559 0.4807 0.124 Uiso 1 1 calc R
C2 C 0.1757(4) 0.7257(8) 0.4171(3) 0.0561(17) Uani 1 1 d .
C3 C 0.2093(4) 0.8338(8) 0.3838(3) 0.0604(19) Uani 1 1 d .
H3A H 0.2416 0.9121 0.3985 0.072 Uiso 1 1 calc R
C4 C 0.1961(4) 0.8286(8) 0.3290(3) 0.0613(19) Uani 1 1 d .
H4A H 0.2179 0.9043 0.3060 0.074 Uiso 1 1 calc R
C5 C 0.1507(3) 0.7112(7) 0.3087(2) 0.0452(14) Uani 1 1 d .
C6 C 0.1172(4) 0.6041(7) 0.3409(3) 0.0542(17) Uani 1 1 d .
H6A H 0.0852 0.5255 0.3260 0.065 Uiso 1 1 calc R
C7 C 0.1300(4) 0.6104(8) 0.3956(3) 0.0606(18) Uani 1 1 d .
H7A H 0.1072 0.5351 0.4183 0.073 Uiso 1 1 calc R
C8 C 0.0639(4) 0.7915(7) 0.2353(2) 0.0558(17) Uani 1 1 d .
H8A H 0.0721 0.9030 0.2418 0.067 Uiso 1 1 calc R
H8B H 0.0204 0.7571 0.2584 0.067 Uiso 1 1 calc R
C9 C 0.0419(3) 0.7671(7) 0.1772(2) 0.0448(15) Uani 1 1 d .
C10 C 0.0848(3) 0.8332(7) 0.1368(2) 0.0480(16) Uani 1 1 d .
H10A H 0.1309 0.8888 0.1450 0.058 Uiso 1 1 calc R
C11 C 0.0610(3) 0.8187(7) 0.0841(2) 0.0502(16) Uani 1 1 d .
H11A H 0.0902 0.8663 0.0563 0.060 Uiso 1 1 calc R
C12 C -0.0046(3) 0.7360(7) 0.0718(2) 0.0453(15) Uani 1 1 d .
C13 C -0.0470(4) 0.6681(7) 0.1122(3) 0.0587(18) Uani 1 1 d .
H13A H -0.0924 0.6103 0.1037 0.070 Uiso 1 1 calc R
C14 C -0.0241(4) 0.6835(8) 0.1647(3) 0.0571(17) Uani 1 1 d .
H14A H -0.0537 0.6365 0.1924 0.068 Uiso 1 1 calc R
C15 C -0.0319(4) 0.7284(9) 0.0153(3) 0.0650(19) Uani 1 1 d .
S1 S 0.15535(8) 0.28981(18) 0.20347(6) 0.0449(4) Uani 1 1 d .
O2 O 0.1400(3) 0.1369(5) 0.22040(19) 0.0805(16) Uani 1 1 d .
O3 O 0.1045(2) 0.4021(5) 0.22659(17) 0.0585(12) Uani 1 1 d .
O4 O 0.2341(2) 0.3369(6) 0.2031(2) 0.0816(16) Uani 1 1 d .
C16 C 0.1284(4) 0.2936(10) 0.1339(3) 0.071(2) Uani 1 1 d .
F4 F 0.0549(3) 0.2574(8) 0.1276(2) 0.130(2) Uani 1 1 d .
F5 F 0.1411(3) 0.4290(6) 0.11258(17) 0.1002(16) Uani 1 1 d .
F6 F 0.1686(3) 0.1912(6) 0.10641(18) 0.1136(18) 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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 '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
C2 O1 C1 117.7(6)
C5 N1 C8 112.3(4)
O1 C2 C7 115.8(6)
O1 C2 C3 124.5(6)
C7 C2 C3 119.6(6)
C2 C3 C4 120.3(6)
C5 C4 C3 118.7(6)
C6 C5 C4 121.8(6)
C6 C5 N1 119.1(5)
C4 C5 N1 119.0(5)
C5 C6 C7 119.3(6)
C2 C7 C6 120.3(6)
N1 C8 C9 112.3(5)
C14 C9 C10 119.5(5)
C14 C9 C8 119.6(5)
C10 C9 C8 120.8(5)
C9 C10 C11 120.1(6)
C12 C11 C10 120.2(6)
C11 C12 C13 119.7(6)
C11 C12 C15 119.7(6)
C13 C12 C15 120.6(6)
C14 C13 C12 120.4(6)
C13 C14 C9 120.1(6)
F1 C15 F2 105.8(6)
F1 C15 F3 105.6(7)
F2 C15 F3 104.6(6)
F1 C15 C12 113.0(6)
F2 C15 C12 114.4(6)
F3 C15 C12 112.6(6)
O2 S1 O4 116.8(3)
O2 S1 O3 113.7(3)
O4 S1 O3 113.1(3)
O2 S1 C16 104.9(4)
O4 S1 C16 103.6(3)
O3 S1 C16 102.7(3)
F5 C16 F4 109.2(7)
F5 C16 F6 107.7(6)
F4 C16 F6 106.4(7)
F5 C16 S1 111.5(5)
F4 C16 S1 111.0(5)
F6 C16 S1 110.8(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.367(7)
O1 C1 1.412(8)
N1 C5 1.481(7)
N1 C8 1.486(7)
F1 C15 1.309(8)
F2 C15 1.310(8)
F3 C15 1.329(8)
C2 C7 1.381(9)
C2 C3 1.379(9)
C3 C4 1.388(9)
C4 C5 1.379(8)
C5 C6 1.356(8)
C6 C7 1.384(9)
C8 C9 1.515(8)
C9 C14 1.381(8)
C9 C10 1.375(8)
C10 C11 1.385(8)
C11 C12 1.370(8)
C12 C13 1.376(8)
C12 C15 1.489(9)
C13 C14 1.377(8)
S1 O2 1.416(5)
S1 O4 1.413(4)
S1 O3 1.430(4)
S1 C16 1.799(7)
C16 F5 1.306(8)
C16 F4 1.311(8)
C16 F6 1.318(8)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21156974 ChemSpider
