#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:28:40 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179531 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/00/4500063.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_4500063
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_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C48 H24 N6, 3(C2 H3 N), 6(C4 H8 O) '
_chemical_formula_sum            'C78 H81 N9 O6'
_chemical_formula_weight         1240.52
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           166
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3 2"'
_symmetry_space_group_name_H-M   'R -3 m :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                   23.6533(2)
_cell_length_b                   23.6533(2)
_cell_length_c                   10.1601(2)
_cell_measurement_reflns_used    8948
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      3.74
_cell_volume                     4922.80(11)
_computing_cell_refinement       'SMART (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_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      100(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart 2000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray Sealed Tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20954
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         3.74
_diffrn_standards_decay_%        1.03
_diffrn_standards_interval_time  1440
_diffrn_standards_number         121
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  0.9500
_exptl_absorpt_correction_T_min  0.7100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1980
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         1090
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0657
_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)+(0.1300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1619
_refine_ls_wR_factor_ref         0.1623
_reflns_number_gt                937
_reflns_number_total             1090
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            deposit.cif
_cod_data_source_block           jiw913
_cod_original_sg_symbol_H-M      R-3m
_cod_database_code               4500063
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'-x, -x+y, -z'
'x-y, -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+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, -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+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'x, x-y, z'
'-x+y, 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+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, 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+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, 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 0.3333 0.60760(4) 0.1667 0.0203(4) Uani 1 2 d S . .
C10 C 0.3333 0.54392(5) 0.1667 0.0241(4) Uani 1 2 d S . .
C11 C 0.31464(12) 0.50474(10) 0.0555(3) 0.0325(5) Uani 0.50 1 d PD A 1
H11 H 0.3009 0.5184 -0.0201 0.039 Uiso 0.50 1 calc P B 1
C12 C 0.31519(13) 0.44592(11) 0.0502(3) 0.0374(5) Uani 0.50 1 d PD A 1
H12 H 0.3039 0.4205 -0.0278 0.045 Uiso 0.50 1 calc P C 1
C11B C 0.34879(12) 0.52169(11) 0.0556(2) 0.0325(5) Uani 0.50 1 d PD A 2
H11B H 0.3598 0.5474 -0.0220 0.039 Uiso 0.50 1 calc P D 2
C12B C 0.34911(13) 0.46326(12) 0.0516(3) 0.0374(5) Uani 0.50 1 d PD A 2
H12B H 0.3597 0.4489 -0.0270 0.045 Uiso 0.50 1 calc P E 2
C13 C 0.3333 0.42608(5) 0.1667 0.0315(4) Uani 1 2 d S . .
C14 C 0.3333 0.36506(6) 0.1667 0.0394(5) Uani 1 2 d S A .
N14 N 0.3333 0.31705(5) 0.1667 0.0543(6) Uani 1 2 d S . .
O20 O 0.88224(10) 0.07970(10) -0.0613(2) 0.0711(8) Uani 0.50 1 d PD F -3
C20 C 0.87942(18) 0.07825(15) 0.0769(3) 0.0738(10) Uani 0.50 1 d PD F -3
H20A H 0.9178 0.0794 0.1187 0.089 Uiso 1 2 calc SR F -3
H20B H 0.8384 0.0416 0.1122 0.089 Uiso 0.50 1 calc PR F -3
C21 C 0.88139(18) 0.14396(15) 0.0812(3) 0.0717(14) Uani 0.50 1 d PD F -3
H21A H 0.8463 0.1408 0.1393 0.086 Uiso 0.50 1 calc PR F -3
H21B H 0.9238 0.1780 0.1169 0.086 Uiso 0.50 1 calc PR F -3
C22 C 0.87206(17) 0.16240(15) -0.0584(3) 0.0756(11) Uani 0.50 1 d PD F -3
H22A H 0.9124 0.2019 -0.0878 0.091 Uiso 0.50 1 calc PR F -3
H22B H 0.8360 0.1722 -0.0593 0.091 Uiso 0.50 1 calc PR F -3
C23 C 0.85621(12) 0.10540(12) -0.15151(18) 0.0738(10) Uani 0.50 1 d PD F -3
H23A H 0.8089 0.0767 -0.1673 0.089 Uiso 0.50 1 calc PR F -3
H23B H 0.8804 0.1191 -0.2358 0.089 Uiso 1 2 calc SR F -3
N30 N 0.97994(12) -0.01058(12) 0.12841(18) 0.0903(16) Uiso 0.50 2 d SPR F -4
C31 C 0.95604(12) 0.00811(12) 0.08031(18) 0.0948(13) Uiso 0.50 1 d PR F -4
H31A H 0.9490 0.0367 0.1396 0.142 Uiso 0.25 1 calc PR F -4
H31B H 0.9138 -0.0274 0.0499 0.142 Uiso 0.25 1 calc PR F -4
H31C H 0.9820 0.0334 0.0045 0.142 Uiso 0.25 1 calc PR F -4
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'
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
C1 C1 C1 27 26_455 119.994(1) y
C1 C1 C10 27 . 120 y
C1 C1 C10 26_455 . 120.002(1) y
C11B C10 C11B 11 . 117.7(2) y
C11B C10 C11 11 11 29.41(10) y
C11B C10 C11 . 11 110.14(13) y
C11B C10 C11 11 . 110.14(13) y
C11B C10 C11 . . 29.41(10) y
C11 C10 C11 11 . 118.8(2) y
C11B C10 C1 11 . 121.16(10) y
C11B C10 C1 . . 121.16(10) y
C11 C10 C1 11 . 120.6(1) y
C11 C10 C1 . . 120.6(1) y
C10 C11 C12 . . 122.5(2) y
C10 C11 H11 . . 118.7 ?
C12 C11 H11 . . 118.7 ?
C11 C12 C13 . . 116.9(2) y
C11 C12 H12 . . 121.5 ?
C13 C12 H12 . . 121.5 ?
C10 C11B C12B . . 122.8(2) y
C10 C11B H11B . . 118.6 ?
C12B C11B H11B . . 118.6 ?
C11B C12B C13 . . 118.1(2) y
C11B C12B H12B . . 121 ?
C13 C12B H12B . . 121 ?
C12B C13 C12B . 11 120.5(2) y
C12B C13 C12 . . 28.60(11) y
C12B C13 C12 11 . 113.50(14) y
C12B C13 C12 . 11 113.50(14) y
C12B C13 C12 11 11 28.60(11) y
C12 C13 C12 . 11 122.2(2) y
C12B C13 C14 . . 119.74(11) y
C12B C13 C14 11 . 119.74(11) y
C12 C13 C14 . . 118.88(11) y
C12 C13 C14 11 . 118.88(11) y
N14 C14 C13 . . 180 y
C23 O20 C20 . . 129.7(2) y
O20 C20 C21 . . 91.5(2) y
O20 C20 H20A . . 113.4 ?
C21 C20 H20A . . 113.4 ?
O20 C20 H20B . . 113.4 ?
C21 C20 H20B . . 113.4 ?
H20A C20 H20B . . 110.7 ?
C22 C21 C20 . . 109.1(2) y
C22 C21 H21A . . 109.9 ?
C20 C21 H21A . . 109.9 ?
C22 C21 H21B . . 109.9 ?
C20 C21 H21B . . 109.9 ?
H21A C21 H21B . . 108.3 ?
C21 C22 C23 . . 109.1(2) y
C21 C22 H22A . . 109.9 ?
C23 C22 H22A . . 109.9 ?
C21 C22 H22B . . 109.9 ?
C23 C22 H22B . . 109.9 ?
H22A C22 H22B . . 108.3 ?
O20 C23 C22 . . 90.61(19) y
O20 C23 H23A . . 113.5 ?
C22 C23 H23A . . 113.5 ?
O20 C23 H23B . . 113.5 ?
C22 C23 H23B . . 113.5 ?
H23A C23 H23B . . 110.8 ?
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 C1 27 1.3971(11) y
C1 C1 26_455 1.3972(11) y
C1 C10 . 1.5063(15) y
C10 C11b 11 1.369(2) y
C10 C11b . 1.369(2) y
C10 C11 11 1.386(2) y
C10 C11 . 1.386(2) y
C11 C12 . 1.399(3) y
C11 H11 . 0.95 ?
C12 C13 . 1.416(3) y
C12 H12 . 0.95 ?
C11b C12b . 1.386(3) y
C11b H11b . 0.95 ?
C12b C13 . 1.397(3) y
C12b H12b . 0.95 ?
C13 C12b 11 1.397(3) y
C13 C12 11 1.416(3) y
C13 C14 . 1.4432(19) y
C14 N14 . 1.136(2) y
O20 C23 . 1.401(3) y
O20 C20 . 1.406(4) y
C20 C21 . 1.532(3) y
C20 H20a . 0.99 ?
C20 H20b . 0.99 ?
C21 C22 . 1.531(4) y
C21 H21a . 0.99 ?
C21 H21b . 0.99 ?
C22 C23 . 1.533(3) y
C22 H22a . 0.99 ?
C22 H22b . 0.99 ?
C23 H23a . 0.99 ?
C23 H23b . 0.99 ?
N30 C31 . 1.0019 y
C31 H31a . 0.98 ?
C31 H31b . 0.98 ?
C31 H31c . 0.98 ?
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
C1 C1 C10 C11B 27 11 105.68(12) y
C1 C1 C10 C11B 26_455 11 -74.32(12) y
C1 C1 C10 C11B 27 . -74.32(12) y
C1 C1 C10 C11B 26_455 . 105.68(12) y
C1 C1 C10 C11 27 11 71.28(12) y
C1 C1 C10 C11 26_455 11 -108.72(12) y
C1 C1 C10 C11 27 . -108.73(12) y
C1 C1 C10 C11 26_455 . 71.28(12) y
C11B C10 C11 C12 11 . -32.3(2) y
C11B C10 C11 C12 . . 78.6(3) y
C11 C10 C11 C12 11 . -1.35(18) y
C1 C10 C11 C12 . . 178.65(18) y
C10 C11 C12 C13 . . 2.6(3) y
C10 C11B C12B C13 . . -0.4(3) y
C11 C12 C13 C12 . 11 -1.22(16) y
C11 C12 C13 C14 . . 178.77(16) y
C12 C13 C14 N14 . . -73(100) y
C12 C13 C14 N14 11 . 107(100) y
C23 O20 C20 C21 . . -33.5(4) y
O20 C20 C21 C22 . . 10.5(3) y
C20 C21 C22 C23 . . 6.4(4) y
C20 O20 C23 C22 . . 37.0(3) y
C21 C22 C23 O20 . . -19.6(3) y
