#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:28:40 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179531 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/00/4500061.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_4500061
loop_
_publ_author_name
'Kenneth E. Maly'
'Thierry Maris'
'Eric Gagnon'
'James D. Wuest'
_publ_section_title
;
 Inclusion Compounds of Hexakis(4-cyanophenyl)benzene: Open Networks
 Maintained by C-H---N Interactions
;
_journal_name_full               'Cryst. Growth & Design'
_journal_page_first              461
_journal_page_last               466
_journal_paper_doi               10.1021/cg050384a
_journal_volume                  6
_journal_year                    2006
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C48 H24 N6, 6(C2 H6 O S), 2(H2 O) '
_chemical_formula_sum            'C60 H64 N6 O8 S6'
_chemical_formula_weight         1189.53
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           155
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'R 3 2"'
_symmetry_space_group_name_H-M   'R 3 2 :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                   23.338(9)
_cell_length_b                   23.338(9)
_cell_length_c                   10.842(9)
_cell_measurement_reflns_used    2903
_cell_measurement_temperature    280(2)
_cell_measurement_theta_max      34.86
_cell_measurement_theta_min      9.72
_cell_volume                     5114(5)
_computing_cell_refinement       'SMART (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      280(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Montel 200 Optics'
_diffrn_radiation_source         'FR 591 Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_av_sigmaI/netI    0.0639
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20949
_diffrn_reflns_theta_full        67.69
_diffrn_reflns_theta_max         67.69
_diffrn_reflns_theta_min         3.79
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  1440
_diffrn_standards_number         112
_exptl_absorpt_coefficient_mu    2.272
_exptl_absorpt_correction_T_max  0.8500
_exptl_absorpt_correction_T_min  0.5200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1878
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), 775 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0732
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0680P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1681
_refine_ls_wR_factor_ref         0.1701
_reflns_number_gt                843
_reflns_number_total             1892
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            deposit.cif
_cod_data_source_block           jiw904
_cod_original_sg_symbol_H-M      R32
_cod_database_code               4500061
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -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'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+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'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0000 -0.0605(4) 0.0000 0.066(2) Uani 1 2 d S . .
C2 C 0.9408(4) -0.0592(4) 0.0000 0.0494(18) Uani 1 2 d S . .
C10 C 1.0000 -0.1246(4) 0.0000 0.060(2) Uani 1 2 d S . .
C11 C 0.9947(4) -0.1586(4) 0.1098(5) 0.097(2) Uani 1 1 d . . .
H11 H 0.9892 -0.1420 0.1862 0.116 Uiso 1 1 calc . . .
C12 C 0.9973(5) -0.2142(4) 0.1071(5) 0.098(2) Uani 1 1 d . . .
H12 H 0.9972 -0.2352 0.1823 0.118 Uiso 1 1 calc . . .
C13 C 1.0000 -0.2411(4) 0.0000 0.082(3) Uani 1 2 d S . .
C14 C 1.0000 -0.3075(6) 0.0000 0.109(4) Uani 1 2 d S . .
N15 N 1.0000 -0.3543(4) 0.0000 0.128(3) Uani 1 2 d S . .
C20 C 0.8760(4) -0.1240(4) 0.0000 0.068(3) Uani 1 2 d S . .
C21 C 0.8477(4) -0.1548(4) 0.1038(5) 0.104(2) Uani 1 1 d . . .
H21 H 0.8689 -0.1343 0.1791 0.125 Uiso 1 1 calc . . .
C22 C 0.7870(4) -0.2171(4) 0.1105(6) 0.111(3) Uani 1 1 d . . .
H22 H 0.7697 -0.2383 0.1873 0.134 Uiso 1 1 calc . . .
C23 C 0.7546(4) -0.2454(4) 0.0000 0.072(3) Uani 1 2 d S . .
C24 C 0.6949(5) -0.3051(5) 0.0000 0.073(3) Uani 1 2 d S . .
N25 N 0.6467(4) -0.3533(4) 0.0000 0.107(3) Uani 1 2 d S . .
S31 S 0.9125(4) -0.2318(4) 0.4380(5) 0.287(3) Uiso 0.729(7) 1 d P A 1
O34 O 0.8993(4) -0.1774(3) 0.3859(6) 0.279(3) Uiso 1 1 d . A 1
C31 C 0.8727(5) -0.2213(3) 0.5934(7) 0.216(4) Uiso 1 1 d . A 1
H31A H 0.9021 -0.1776 0.6288 0.325 Uiso 1 1 calc R A 1
H31B H 0.8670 -0.2556 0.6524 0.325 Uiso 1 1 calc R A 1
H31C H 0.8296 -0.2257 0.5751 0.325 Uiso 1 1 calc R A 1
C32 C 0.8410(7) -0.2961(5) 0.4195(8) 0.269(5) Uiso 1 1 d . A 1
H32A H 0.8074 -0.2827 0.4136 0.403 Uiso 1 1 calc R A 1
H32B H 0.8310 -0.3260 0.4899 0.403 Uiso 1 1 calc R A 1
H32C H 0.8408 -0.3190 0.3435 0.403 Uiso 1 1 calc R A 1
S32 S 0.8586(3) -0.2282(3) 0.4385(6) 0.100(3) Uiso 0.271(7) 1 d P A 2
O33 O 0.9617(3) -0.0134(12) 0.4190(7) 0.125(4) Uani 0.3333 1 d P . .
H31 H 0.9458 -0.0478 0.3708 0.300 Uiso 0.3333 1 d PR . .
H32 H 1.0000 0.0000 0.3864 0.300 Uiso 1 3 d SR . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C2 . 2_645 117.80(13) y
C2 C1 C10 . . 121.1(6) y
C2 C1 C10 2_645 . 121.1(6) y
C1 C2 C1 . 3_765 122.20(13) y
C1 C2 C20 . . 118.9(6) y
C1 C2 C20 3_765 . 118.9(6) y
C11 C10 C11 6_765 . 116.9(7) y
C11 C10 C1 6_765 . 121.5(4) y
C11 C10 C1 . . 121.5(4) y
C12 C11 C10 . . 120.0(6) y
C12 C11 H11 . . 120 ?
C10 C11 H11 . . 120 ?
C11 C12 C13 . . 120.9(6) y
C11 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C12 C13 C12 . 6_765 121.0(8) y
C12 C13 C14 . . 119.5(4) y
C12 C13 C14 6_765 . 119.5(4) y
N15 C14 C13 . . 180.000(2) y
C21 C20 C21 4_645 . 117.2(9) y
C21 C20 C2 4_645 . 121.4(4) y
C21 C20 C2 . . 121.4(4) y
C20 C21 C22 . . 124.3(7) y
C20 C21 H21 . . 117.8 ?
C22 C21 H21 . . 117.8 ?
C23 C22 C21 . . 117.6(6) y
C23 C22 H22 . . 121.2 ?
C21 C22 H22 . . 121.2 ?
C22 C23 C22 . 4_645 118.9(8) y
C22 C23 C24 . . 120.5(4) y
C22 C23 C24 4_645 . 120.5(4) y
N25 C24 C23 . . 179.997(2) y
O34 S31 C32 . . 100.3(7) y
O34 S31 C31 . . 84.9(5) y
C32 S31 C31 . . 83.7(6) y
O33 O33 H31 2_645 . 80.2 ?
O33 O33 H31 3_765 . 126.2 ?
H31 O33 H32 . . 88.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.397(14) y
C1 C2 2_645 1.397(14) y
C2 C1 3_765 1.397(14) y
C1 C10 . 1.495(11) y
C2 C20 . 1.514(12) y
C10 C11 6_765 1.403(7) y
C10 C11 . 1.403(7) y
C11 C12 . 1.330(8) y
C11 H11 . 0.95 ?
C12 C13 . 1.336(7) y
C12 H12 . 0.95 ?
C13 C12 6_765 1.336(7) y
C13 C14 . 1.550(15) y
C14 N15 . 1.091(12) y
C20 C21 4_645 1.320(7) y
C20 C21 . 1.320(7) y
C21 C22 . 1.439(9) y
C21 H21 . 0.95 ?
C22 C23 . 1.394(7) y
C22 H22 . 0.95 ?
C23 C22 4_645 1.394(7) y
C23 C24 . 1.395(13) y
C24 N25 . 1.124(11) y
S31 O34 . 1.556(9) y
S31 C32 . 1.605(11) y
S31 C31 . 1.997(10) y
C31 H31a . 0.98 ?
C31 H31b . 0.98 ?
C31 H31c . 0.98 ?
C32 H32a . 0.98 ?
C32 H32b . 0.98 ?
C32 H32c . 0.98 ?
O33 O33 2_645 1.360(11) y
O33 O33 3_765 1.360(11) y
O33 H31 . 0.8697 ?
O33 H32 . 0.8616 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 C1 C2 C1 2_645 3_765 0 y
C10 C1 C2 C1 . 3_765 180 y
C2 C1 C2 C20 2_645 . 180 y
C10 C1 C2 C20 . . 0 y
C2 C1 C10 C11 . 6_765 95.2(4) y
C2 C1 C10 C11 2_645 6_765 -84.8(4) y
C2 C1 C10 C11 . . -84.8(4) y
C2 C1 C10 C11 2_645 . 95.2(4) y
C1 C10 C11 C12 . . -177.5(6) y
C10 C11 C12 C13 . . -5.0(16) y
C11 C12 C13 C14 . . -177.4(6) y
C1 C2 C20 C21 . 4_645 -92.6(9) y
C1 C2 C20 C21 3_765 4_645 87.4(9) y
C1 C2 C20 C21 . . 87.4(9) y
C1 C2 C20 C21 3_765 . -92.6(9) y
C21 C20 C21 C22 4_645 . 1.4(16) y
C2 C20 C21 C22 . . -178.5(6) y
C20 C21 C22 C23 . . -2.7(15) y
C21 C22 C23 C22 . 4_645 1.2(14) y
C21 C22 C23 C24 . . -178.7(5) y
