#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:28:40 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179531 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/00/4500056.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_4500056
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 unk
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C48 H24 N6, 2(C H4 O)'
_chemical_formula_sum            'C50 H32 N6 O2'
_chemical_formula_weight         748.82
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           94
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4n 2n'
_symmetry_space_group_name_H-M   'P 42 21 2'
_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            2
_cell_length_a                   15.118(2)
_cell_length_b                   15.118(2)
_cell_length_c                   9.1050(18)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    276(2)
_cell_measurement_theta_max      56.00
_cell_measurement_theta_min      2.10
_cell_volume                     2081.0(6)
_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      276(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart 2000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            26501
_diffrn_reflns_theta_full        68.36
_diffrn_reflns_theta_max         68.36
_diffrn_reflns_theta_min         4.14
_diffrn_standards_decay_%        -0.90
_diffrn_standards_number         128
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), 760 Friedel Pairs'
_refine_ls_extinction_coef       0.0028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1006P)²+0.0922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1602
_reflns_number_gt                1608
_reflns_number_total             1908
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            deposit.cif
_cod_data_source_block           jiw892
_cod_original_sg_symbol_H-M      P42212
_cod_database_code               4500056
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'y, x, -z'
'-y, -x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.41047(8) 0.47584(8) 0.00065(15) 0.0733(3) Uani 1 1 d . . .
C2 C 0.43437(8) 0.56563(8) 0.0000 0.0746(4) Uani 1 2 d S . .
C10 C 0.31456(8) 0.45135(8) 0.00268(16) 0.0724(3) Uani 1 1 d . . .
N10 N -0.02891(10) 0.36570(14) 0.0163(2) 0.1337(6) Uani 1 1 d . . .
C11 C 0.27285(9) 0.41732(10) -0.11966(17) 0.0860(4) Uani 1 1 d . . .
H11 H 0.3053 0.4090 -0.2053 0.103 Uiso 1 1 calc R . .
C12 C 0.18475(9) 0.39541(11) -0.11830(18) 0.0893(4) Uani 1 1 d . . .
H12 H 0.1581 0.3727 -0.2022 0.107 Uiso 1 1 calc R . .
C13 C 0.13603(8) 0.40729(9) 0.00803(17) 0.0803(4) Uani 1 1 d . . .
C14 C 0.17599(9) 0.44215(10) 0.13126(17) 0.0856(4) Uani 1 1 d . . .
H14 H 0.1431 0.4510 0.2163 0.103 Uiso 1 1 calc R . .
C15 C 0.26428(9) 0.46394(9) 0.12894(17) 0.0813(4) Uani 1 1 d . . .
H15 H 0.2907 0.4873 0.2126 0.098 Uiso 1 1 calc R . .
C16 C 0.04290(10) 0.38364(12) 0.0131(2) 0.0968(5) Uani 1 1 d . . .
C20 C 0.36425(9) 0.63575(9) 0.0000 0.0752(4) Uani 1 2 d S . .
N20 N 0.11639(12) 0.88361(12) 0.0000 0.1700(10) Uani 1 2 d S . .
C21 C 0.35147(10) 0.68886(9) 0.12145(18) 0.0887(4) Uani 1 1 d . . .
H21 H 0.3869 0.6814 0.2040 0.106 Uiso 1 1 calc R . .
C22 C 0.28711(10) 0.75231(10) 0.1214(2) 0.0966(5) Uani 1 1 d . . .
H22 H 0.2786 0.7872 0.2044 0.116 Uiso 1 1 calc R . .
C23 C 0.23500(9) 0.76500(9) 0.0000 0.0887(5) Uani 1 2 d S . .
C24 C 0.16786(12) 0.83214(12) 0.0000 0.1156(8) Uani 1 2 d S . .
C100 C 0.0970(4) 0.1579(5) -0.0024(8) 0.193(3) Uani 0.50 1 d P A -1
H10A H 0.0844 0.2114 0.0506 0.289 Uiso 0.50 1 calc PR A -1
H10B H 0.0619 0.1561 -0.0902 0.289 Uiso 0.50 1 calc PR A -1
H10C H 0.1586 0.1566 -0.0281 0.289 Uiso 0.50 1 calc PR A -1
O100 O 0.0749(5) 0.0773(5) 0.0947(11) 0.307(4) Uani 0.50 1 d P A -1
H100 H 0.0313 0.0519 0.0615 0.461 Uiso 0.50 1 calc P B -1
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
_geom_angle_publ_flag
C1 C1 C2 7 120.09(8) y
C1 C1 C10 7 120.68(6) y
C2 C1 C10 . 119.23(11) y
C1 C2 C1 8_665 119.81(16) y
C1 C2 C20 8_665 120.09(8) y
C1 C2 C20 . 120.09(8) y
C11 C10 C15 . 117.93(12) y
C11 C10 C1 . 121.68(13) y
C15 C10 C1 . 120.38(12) y
C12 C11 C10 . 121.76(14) y
C12 C11 H11 . 119.1 ?
C10 C11 H11 . 119.1 ?
C11 C12 C13 . 119.66(14) y
C11 C12 H12 . 120.2 ?
C13 C12 H12 . 120.2 ?
C12 C13 C14 . 119.67(12) y
C12 C13 C16 . 120.80(14) y
C14 C13 C16 . 119.52(14) y
C15 C14 C13 . 120.28(14) y
C15 C14 H14 . 119.9 ?
C13 C14 H14 . 119.9 ?
C14 C15 C10 . 120.69(13) y
C14 C15 H15 . 119.7 ?
C10 C15 H15 . 119.7 ?
N10 C16 C13 . 179.6(2) y
C21 C20 C21 8_665 118.62(18) y
C21 C20 C2 8_665 120.69(9) y
C21 C20 C2 . 120.69(9) y
C22 C21 C20 . 120.53(15) y
C22 C21 H21 . 119.7 ?
C20 C21 H21 . 119.7 ?
C21 C22 C23 . 120.51(16) y
C21 C22 H22 . 119.7 ?
C23 C22 H22 . 119.7 ?
C22 C23 C22 8_665 119.30(19) y
C22 C23 C24 8_665 120.35(10) y
C22 C23 C24 . 120.35(10) y
N20 C24 C23 . 180.0(2) y
C100 O100 H100 . 109.5 ?
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 C1 7 1.398(3) y
C1 C2 . 1.4047(15) y
C1 C10 . 1.4966(17) y
C2 C1 8_665 1.4047(15) y
C2 C20 . 1.499(3) y
C10 C11 . 1.380(2) y
C10 C15 . 1.391(2) y
N10 C16 . 1.119(2) y
C11 C12 . 1.373(2) y
C11 H11 . 0.93 ?
C12 C13 . 1.378(2) y
C12 H12 . 0.93 ?
C13 C14 . 1.379(2) y
C13 C16 . 1.4534(19) y
C14 C15 . 1.375(2) y
C14 H14 . 0.93 ?
C15 H15 . 0.93 ?
C20 C21 8_665 1.3802(18) y
C20 C21 . 1.3802(18) y
N20 C24 . 1.100(3) y
C21 C22 . 1.366(2) y
C21 H21 . 0.93 ?
C22 C23 . 1.371(2) y
C22 H22 . 0.93 ?
C23 C22 8_665 1.371(2) y
C23 C24 . 1.435(3) y
C100 O100 . 1.542(10) y
C100 H10a . 0.96 ?
C100 H10b . 0.96 ?
C100 H10c . 0.96 ?
O100 H100 . 0.82 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O100 H100 O100 0.82 2.55 3.255(13) 145.3 2
O100 H100 N20 0.82 2.5 3.074(8) 128.1 2_565
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 C2 C1 7 8_665 -0.56(13) y
C10 C1 C2 C1 . 8_665 179.47(14) y
C1 C1 C2 C20 7 . 179.44(13) y
C10 C1 C2 C20 . . -0.53(14) y
C1 C1 C10 C11 7 . -72.9(2) y
C2 C1 C10 C11 . . 107.08(14) y
C1 C1 C10 C15 7 . 108.22(19) y
C2 C1 C10 C15 . . -71.81(16) y
C15 C10 C11 C12 . . -0.6(2) y
C1 C10 C11 C12 . . -179.53(13) y
C10 C11 C12 C13 . . -0.1(2) y
C11 C12 C13 C14 . . 0.8(2) y
C11 C12 C13 C16 . . -179.24(15) y
C12 C13 C14 C15 . . -0.8(2) y
C16 C13 C14 C15 . . 179.25(15) y
C13 C14 C15 C10 . . 0.1(2) y
C11 C10 C15 C14 . . 0.6(2) y
C1 C10 C15 C14 . . 179.55(13) y
C1 C2 C20 C21 8_665 8_665 111.02(10) y
C1 C2 C20 C21 . 8_665 -68.98(10) y
C1 C2 C20 C21 8_665 . -68.98(10) y
C1 C2 C20 C21 . . 111.02(10) y
C21 C20 C21 C22 8_665 . 0.43(11) y
C2 C20 C21 C22 . . -179.57(11) y
C20 C21 C22 C23 . . -0.9(2) y
C21 C22 C23 C22 . 8_665 0.44(11) y
C21 C22 C23 C24 . . -179.56(11) y
