#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:27:37 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178900 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/29/4112997.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_4112997
loop_
_publ_author_name
'Christos A. Ilioudis'
'Derek A. Tocher'
'Jonathan W. Steed'
_publ_section_title
;
 A Highly Efficient, Preorganized Macrobicyclic Receptor for Halides Based
 on CH... and NH...Anion Interactions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12395
_journal_page_last               12402
_journal_paper_doi               10.1021/ja047070g
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C69 H87 Cl6 N7 O12 S6'
_chemical_formula_weight         1611.61
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           146
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_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                120.00
_cell_formula_units_Z            3
_cell_length_a                   16.3404(23)
_cell_length_b                   16.3404(23)
_cell_length_c                   28.0178(27)
_cell_measurement_temperature    120(2)
_cell_volume                     6478.7(14)
_computing_cell_refinement       'DENZO SMN'
_computing_data_collection       'NONIUS COLLECT'
_computing_data_reduction        'DENZO SMN'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'KAPPA CCD'
_diffrn_measurement_method       '2o phi frames'
_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  0.1939
_diffrn_reflns_av_sigmaI/netI    0.3169
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            10189
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.97
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.400
_exptl_absorpt_correction_type   scalepack
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       plate
_exptl_crystal_F_000             2514
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.515
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.169
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(2)
_refine_ls_extinction_coef       0.0021(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.498
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         5656
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.496
_refine_ls_R_factor_all          0.2773
_refine_ls_R_factor_gt           0.2118
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3166
_refine_ls_wR_factor_ref         0.3388
_reflns_number_gt                3732
_reflns_number_total             5656
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja047070gsi20040519_073146.cif
_cod_data_source_block           c:\structs\chris\tc2\rhomt2
_cod_original_cell_volume        6479.0(18)
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               4112997
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
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
S1 S 0.82855(18) 0.10476(19) 0.12616(10) 0.0202(7) Uani 1 1 d .
S2 S 0.6398(2) -0.1806(2) -0.00621(10) 0.0245(7) Uani 1 1 d .
O1 O 0.8371(5) 0.1131(6) 0.0750(3) 0.030(2) Uani 1 1 d .
O3 O 0.5883(5) -0.1682(6) 0.0313(3) 0.034(2) Uani 1 1 d .
N1 N 1.0000 0.0000 0.1972(6) 0.017(4) Uani 1 3 d S
C16 C 0.5798(8) -0.3015(8) -0.0241(4) 0.022(3) Uani 1 1 d U
O2 O 0.8842(6) 0.1844(6) 0.1546(3) 0.033(2) Uani 1 1 d .
C7 C 0.8457(7) 0.0007(8) 0.1942(4) 0.018(2) Uani 1 1 d .
H7A H 0.8090 -0.0687 0.1987 0.021 Uiso 1 1 calc R
H7B H 0.8117 0.0281 0.2110 0.021 Uiso 1 1 calc R
N2 N 0.8489(6) 0.0217(7) 0.1424(3) 0.025(2) Uani 1 1 d .
C13 C 0.5480(10) -0.0068(12) 0.1186(5) 0.052(4) Uani 1 1 d .
H13 H 0.4998 -0.0388 0.0954 0.062 Uiso 1 1 calc R
C1 C 0.9859(7) -0.0915(7) -0.0125(4) 0.018(2) Uani 1 1 d U
H1 H 0.9755 -0.1542 -0.0129 0.022 Uiso 1 1 calc R
O4 O 0.6614(7) -0.1234(6) -0.0481(3) 0.041(2) Uani 1 1 d .
C2 C 0.9081(8) -0.0756(7) -0.0122(3) 0.014(2) Uani 1 1 d .
C21 C 0.6002(7) -0.3262(8) -0.0671(4) 0.020(3) Uani 1 1 d U
H21 H 0.6428 -0.2786 -0.0883 0.025 Uiso 1 1 calc R
C5 C 0.7444(8) -0.1398(8) 0.1054(4) 0.022(3) Uani 1 1 d U
H5A H 0.6947 -0.1221 0.1040 0.027 Uiso 1 1 calc R
H5B H 0.7349 -0.1762 0.1351 0.027 Uiso 1 1 calc R
C18 C 0.4669(9) -0.4632(9) -0.0089(5) 0.036(3) Uani 1 1 d .
H18 H 0.4199 -0.5101 0.0111 0.044 Uiso 1 1 calc R
C14 C 0.6378(8) 0.0157(8) 0.1083(4) 0.029(3) Uani 1 1 d U
H14 H 0.6515 -0.0057 0.0794 0.035 Uiso 1 1 calc R
N3 N 0.7409(6) -0.1595(6) 0.0161(3) 0.025(2) Uani 1 1 d .
C4 C 0.7332(8) -0.2014(8) 0.0636(4) 0.023(3) Uani 1 1 d U
H4A H 0.7817 -0.2206 0.0659 0.028 Uiso 1 1 calc R
H4B H 0.6706 -0.2595 0.0659 0.028 Uiso 1 1 calc R
C3 C 0.8089(8) -0.1623(9) -0.0175(4) 0.027(3) Uani 1 1 d .
H3B H 0.7864 -0.1651 -0.0505 0.033 Uiso 1 1 calc R
H3A H 0.8123 -0.2203 -0.0117 0.033 Uiso 1 1 calc R
C10 C 0.6859(9) 0.0962(10) 0.1826(4) 0.034(3) Uani 1 1 d .
H10 H 0.7353 0.1347 0.2041 0.041 Uiso 1 1 calc R
C6 C 0.8384(7) -0.0522(7) 0.1073(4) 0.019(2) Uani 1 1 d .
H6B H 0.8530 -0.0234 0.0751 0.023 Uiso 1 1 calc R
H6A H 0.8864 -0.0704 0.1148 0.023 Uiso 1 1 calc R
C9 C 0.7104(8) 0.0708(9) 0.1405(4) 0.023(3) Uani 1 1 d .
C17 C 0.5107(8) -0.3680(10) 0.0039(5) 0.038(3) Uani 1 1 d .
H17 H 0.4923 -0.3497 0.0323 0.045 Uiso 1 1 calc R
C8 C 0.9402(8) 0.0375(8) 0.2167(4) 0.025(3) Uani 1 1 d U
C11 C 0.6016(11) 0.0717(11) 0.1949(5) 0.047(4) Uani 1 1 d .
H11 H 0.5887 0.0895 0.2250 0.056 Uiso 1 1 calc R
C19 C 0.4926(8) -0.4882(8) -0.0508(6) 0.037(4) Uani 1 1 d .
C20 C 0.5594(8) -0.4199(8) -0.0798(4) 0.028(3) Uani 1 1 d U
H20 H 0.5775 -0.4372 -0.1086 0.033 Uiso 1 1 calc R
C12 C 0.5258(11) 0.0157(12) 0.1614(7) 0.058(4) Uani 1 1 d .
Cl1 Cl 0.4921(9) 0.1436(8) 0.0559(5) 0.212(5) Uani 1 1 d .
Cl2 Cl 0.4568(18) 0.1933(12) -0.0323(5) 0.324(11) Uani 1 1 d .
C22 C 0.4494(11) -0.5910(14) -0.0642(8) 0.082(6) Uani 1 1 d .
H22A H 0.4775 -0.6204 -0.0447 0.123 Uiso 1 1 calc R
H22C H 0.4617 -0.5960 -0.0980 0.123 Uiso 1 1 calc R
H22B H 0.3811 -0.6233 -0.0587 0.123 Uiso 1 1 calc R
C15 C 0.4158(13) -0.0204(15) 0.1719(8) 0.082(6) Uani 1 1 d U
H15B H 0.4038 0.0323 0.1681 0.123 Uiso 1 1 calc R
H15A H 0.4003 -0.0447 0.2046 0.123 Uiso 1 1 calc R
H15C H 0.3764 -0.0709 0.1494 0.123 Uiso 1 1 calc R
C23 C 0.4819(19) 0.2307(18) 0.0205(9) 0.112(8) Uani 1 1 d U
H23A H 0.4317 0.2412 0.0337 0.134 Uiso 1 1 calc R
H23B H 0.5423 0.2915 0.0211 0.134 Uiso 1 1 calc R
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'
S S 0.1246 0.1234 '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
O2 S1 O1 119.4(5) . .
O2 S1 N2 108.0(5) . .
O1 S1 N2 108.0(5) . .
O2 S1 C9 105.1(5) . .
O1 S1 C9 107.1(5) . .
N2 S1 C9 108.9(5) . .
O3 S2 O4 118.9(5) . .
O3 S2 N3 107.1(5) . .
O4 S2 N3 106.4(5) . .
O3 S2 C16 109.2(5) . .
O4 S2 C16 108.3(5) . .
N3 S2 C16 106.2(5) . .
C8 N1 C8 107.4(8) 3_765 .
C8 N1 C8 107.4(8) 3_765 2_645
C8 N1 C8 107.4(8) . 2_645
C17 C16 C21 120.2(11) . .
C17 C16 S2 120.1(10) . .
C21 C16 S2 119.7(9) . .
N2 C7 C8 114.2(9) . .
C7 N2 C6 118.5(9) . .
C7 N2 S1 118.1(7) . .
C6 N2 S1 120.2(7) . .
C14 C13 C12 121.1(14) . .
C2 C1 C2 119.5(10) 2_645 .
C1 C2 C1 120.5(10) 3_765 .
C1 C2 C3 121.8(10) 3_765 .
C1 C2 C3 117.4(9) . .
C16 C21 C20 120.2(11) . .
C6 C5 C4 113.3(9) . .
C19 C18 C17 119.2(12) . .
C13 C14 C9 119.4(11) . .
C4 N3 C3 116.9(9) . .
C4 N3 S2 113.9(7) . .
C3 N3 S2 116.7(8) . .
N3 C4 C5 116.2(9) . .
N3 C3 C2 112.1(9) . .
C11 C10 C9 124.7(13) . .
C5 C6 N2 116.5(9) . .
C10 C9 C14 117.8(10) . .
C10 C9 S1 122.5(9) . .
C14 C9 S1 119.8(8) . .
C16 C17 C18 120.1(13) . .
C7 C8 N1 116.1(9) . .
C10 C11 C12 118.1(13) . .
C20 C19 C18 120.1(11) . .
C20 C19 C22 119.8(14) . .
C18 C19 C22 120.1(14) . .
C19 C20 C21 119.9(11) . .
C13 C12 C11 118.7(13) . .
C13 C12 C15 117.5(17) . .
C11 C12 C15 123.8(16) . .
Cl2 C23 Cl1 108.6(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.405(9) .
S1 O1 1.439(9) .
S1 N2 1.616(10) .
S1 C9 1.768(11) .
S2 O3 1.423(8) .
S2 O4 1.431(9) .
S2 N3 1.634(9) .
S2 C16 1.783(12) .
N1 C8 1.492(13) 3_765
N1 C8 1.492(13) .
N1 C8 1.492(13) 2_645
C16 C17 1.358(16) .
C16 C21 1.364(16) .
C7 N2 1.487(14) .
C7 C8 1.487(15) .
N2 C6 1.500(14) .
C13 C14 1.354(18) .
C13 C12 1.36(2) .
C1 C2 1.364(14) 2_645
C1 C2 1.418(15) .
C2 C1 1.364(14) 3_765
C2 C3 1.536(15) .
C21 C20 1.376(16) .
C5 C6 1.487(15) .
C5 C4 1.496(16) .
C18 C19 1.376(19) .
C18 C17 1.395(18) .
C14 C9 1.401(16) .
N3 C4 1.472(14) .
N3 C3 1.474(14) .
C10 C11 1.274(18) .
C10 C9 1.375(16) .
C11 C12 1.46(2) .
C19 C20 1.370(18) .
C19 C22 1.51(2) .
C12 C15 1.61(2) .
Cl1 C23 1.81(2) .
Cl2 C23 1.57(3) .
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_4
O3 S2 C16 C17 -14.4(11) . .
O4 S2 C16 C17 -145.2(9) . .
N3 S2 C16 C17 100.8(10) . .
O3 S2 C16 C21 162.3(9) . .
O4 S2 C16 C21 31.5(10) . .
N3 S2 C16 C21 -82.5(9) . .
C8 C7 N2 C6 96.1(11) . .
C8 C7 N2 S1 -103.9(10) . .
O2 S1 N2 C7 48.7(9) . .
O1 S1 N2 C7 179.0(7) . .
C9 S1 N2 C7 -65.0(9) . .
O2 S1 N2 C6 -151.7(8) . .
O1 S1 N2 C6 -21.3(9) . .
C9 S1 N2 C6 94.6(8) . .
C2 C1 C2 C1 1(2) 2_645 3_765
C2 C1 C2 C3 174.2(8) 2_645 .
C17 C16 C21 C20 -8.0(16) . .
S2 C16 C21 C20 175.3(8) . .
C12 C13 C14 C9 -6(2) . .
O3 S2 N3 C4 42.9(9) . .
O4 S2 N3 C4 171.1(8) . .
C16 S2 N3 C4 -73.7(8) . .
O3 S2 N3 C3 -176.2(8) . .
O4 S2 N3 C3 -48.0(9) . .
C16 S2 N3 C3 67.2(9) . .
C3 N3 C4 C5 126.9(11) . .
S2 N3 C4 C5 -92.3(10) . .
C6 C5 C4 N3 -61.3(13) . .
C4 N3 C3 C2 -88.5(12) . .
S2 N3 C3 C2 131.8(9) . .
C1 C2 C3 N3 -50.7(14) 3_765 .
C1 C2 C3 N3 136.3(10) . .
C4 C5 C6 N2 168.7(9) . .
C7 N2 C6 C5 67.6(12) . .
S1 N2 C6 C5 -91.9(11) . .
C11 C10 C9 C14 1(2) . .
C11 C10 C9 S1 -178.4(12) . .
C13 C14 C9 C10 2.9(18) . .
C13 C14 C9 S1 -177.3(11) . .
O2 S1 C9 C10 -21.9(12) . .
O1 S1 C9 C10 -149.8(11) . .
N2 S1 C9 C10 93.7(11) . .
O2 S1 C9 C14 158.3(9) . .
O1 S1 C9 C14 30.4(11) . .
N2 S1 C9 C14 -86.1(10) . .
C21 C16 C17 C18 6.4(17) . .
S2 C16 C17 C18 -176.9(9) . .
C19 C18 C17 C16 -1.9(18) . .
N2 C7 C8 N1 -61.0(13) . .
C8 N1 C8 C7 168.0(9) 3_765 .
C8 N1 C8 C7 -76.6(15) 2_645 .
C9 C10 C11 C12 -2(2) . .
C17 C18 C19 C20 -1.0(18) . .
C17 C18 C19 C22 177.1(13) . .
C18 C19 C20 C21 -0.6(18) . .
C22 C19 C20 C21 -178.7(12) . .
C16 C21 C20 C19 5.0(17) . .
C14 C13 C12 C11 5(2) . .
C14 C13 C12 C15 -175.7(15) . .
C10 C11 C12 C13 -1(2) . .
C10 C11 C12 C15 180.0(15) . .
