#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:27:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178783 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/37/4103733.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_4103733
loop_
_publ_author_name
'Kenneth E. Maly'
'Thierry Maris'
'James D. Wuest'
_publ_section_title
;
 Engineering Hydrogen-Bonded Molecular Crystals Built from Derivatives of
 Hexaphenylbenzene and Related Compounds
;
_journal_name_full               'J. Am. Chem. Soc.'
_journal_page_first              4306
_journal_page_last               4322
_journal_paper_doi               10.1021/ja067571x
_journal_volume                  129
_journal_year                    2007
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C60 H48 N30'
_chemical_formula_sum            'C60 H48 N30'
_chemical_formula_weight         1189.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_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                   22.8070(9)
_cell_length_b                   22.8070(9)
_cell_length_c                   17.2915(16)
_cell_measurement_reflns_used    12264
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      50.36
_cell_measurement_theta_min      3.40
_cell_volume                     7789.3(8)
_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      200(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.057
_diffrn_reflns_av_sigmaI/netI    0.0563
_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       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33045
_diffrn_reflns_theta_full        53.34
_diffrn_reflns_theta_max         53.34
_diffrn_reflns_theta_min         3.40
_diffrn_standards_decay_%        -0.61
_diffrn_standards_number         183
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.9400
_exptl_absorpt_correction_T_min  0.9000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    0.761
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1854
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0614
_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)+(0.0870P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1520
_reflns_number_gt                1259
_reflns_number_total             2012
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            deposit.cif
_cod_data_source_block           jiw992
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               4103733
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'
'-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
C1 C -0.06313(11) -0.06151(11) 0.00269(15) 0.0406(8) Uani 1 1 d .
C2 C -0.12962(12) -0.12529(12) 0.0073(2) 0.0452(8) Uani 1 1 d .
C3 C -0.15393(15) -0.15064(16) 0.0804(2) 0.0722(10) Uani 1 1 d .
H3 H -0.1292 -0.1272 0.1252 0.087 Uiso 1 1 calc R
C4 C -0.21530(15) -0.21119(15) 0.0871(2) 0.0670(10) Uani 1 1 d .
H4 H -0.2320 -0.2284 0.1373 0.080 Uiso 1 1 calc R
C5 C -0.25285(12) -0.24726(12) 0.0233(2) 0.0467(8) Uani 1 1 d .
C6 C -0.22667(15) -0.22037(15) -0.0483(2) 0.0686(9) Uani 1 1 d .
H6 H -0.2512 -0.2442 -0.0930 0.082 Uiso 1 1 calc R
C7 C -0.16622(17) -0.16017(17) -0.0580(2) 0.0799(10) Uani 1 1 d .
H7 H -0.1500 -0.1430 -0.1083 0.096 Uiso 1 1 calc R
C8 C -0.31581(13) -0.30730(13) 0.0365(2) 0.0541(9) Uani 1 1 d .
C9 C -0.40554(17) -0.38212(16) 0.1140(3) 0.0678(9) Uani 1 1 d .
C10 C -0.40779(15) -0.40383(16) -0.0230(3) 0.0614(9) Uani 1 1 d .
N1 N -0.34546(11) -0.34515(11) -0.02895(16) 0.0606(7) Uani 1 1 d .
N2 N -0.34265(14) -0.32291(13) 0.1101(2) 0.0814(9) Uani 1 1 d .
N3 N -0.43749(12) -0.42211(11) 0.0497(2) 0.0660(8) Uani 1 1 d .
N4 N -0.43294(14) -0.39925(13) 0.1811(2) 0.0788(9) Uani 1 1 d .
H4A H -0.4723 -0.4366 0.1867 0.095 Uiso 1 1 calc R
H4B H -0.4124 -0.3737 0.2215 0.095 Uiso 1 1 calc R
N5 N -0.43640(12) -0.43909(12) -0.08097(18) 0.0706(8) Uani 1 1 d .
H5A H -0.4170 -0.4268 -0.1267 0.085 Uiso 1 1 calc R
H5B H -0.4760 -0.4762 -0.0762 0.085 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 0.0181 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'
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 11 12 119.58(5) y
C1 C1 C2 11 . 119.34(17) y
C1 C1 C2 12 . 120.89(17) y
C3 C2 C7 . . 120.0(3) y
C3 C2 C1 . . 117.1(3) y
C7 C2 C1 . . 122.8(3) y
C2 C3 C4 . . 118.9(3) y
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C5 C4 C3 . . 122.5(3) y
C5 C4 H4 . . 118.8 ?
C3 C4 H4 . . 118.8 ?
C6 C5 C4 . . 116.7(2) y
C6 C5 C8 . . 125.2(3) y
C4 C5 C8 . . 118.0(3) y
C5 C6 C7 . . 123.0(3) y
C5 C6 H6 . . 118.5 ?
C7 C6 H6 . . 118.5 ?
C6 C7 C2 . . 118.8(3) y
C6 C7 H7 . . 120.6 ?
C2 C7 H7 . . 120.6 ?
N2 C8 N1 . . 125.5(2) y
N2 C8 C5 . . 120.1(3) y
N1 C8 C5 . . 114.5(3) y
N4 C9 N3 . . 120.5(3) y
N4 C9 N2 . . 116.6(4) y
N3 C9 N2 . . 122.9(4) y
N5 C10 N1 . . 121.1(4) y
N5 C10 N3 . . 121.0(3) y
N1 C10 N3 . . 117.9(3) y
C8 N1 C10 . . 119.2(3) y
C8 N2 C9 . . 113.8(3) y
C10 N3 C9 . . 120.6(3) y
C9 N4 H4A . . 120 ?
C9 N4 H4B . . 120 ?
H4A N4 H4B . . 120 ?
C10 N5 H5A . . 120 ?
C10 N5 H5B . . 120 ?
H5A N5 H5B . . 120 ?
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 11 1.425(2) y
C1 C1 12 1.425(5) y
C1 C2 . 1.489(3) y
C2 C3 . 1.385(4) y
C2 C7 . 1.393(4) y
C3 C4 . 1.395(4) y
C3 H3 . 0.95 ?
C4 C5 . 1.387(4) y
C4 H4 . 0.95 ?
C5 C6 . 1.378(4) y
C5 C8 . 1.422(4) y
C6 C7 . 1.386(4) y
C6 H6 . 0.95 ?
C7 H7 . 0.95 ?
C8 N2 . 1.378(4) y
C8 N1 . 1.379(4) y
C9 N4 . 1.281(4) y
C9 N3 . 1.392(4) y
C9 N2 . 1.396(4) y
C10 N5 . 1.246(4) y
C10 N1 . 1.386(4) y
C10 N3 . 1.389(4) y
N4 H4a . 0.88 ?
N4 H4b . 0.88 ?
N5 H5a . 0.88 ?
N5 H5b . 0.88 ?
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
N4 H4B N1 0.88 2.14 2.975(4) 157.1 6_445
N5 H5B N3 0.88 2.21 3.079(3) 167.2 10_445
N5 H5A N2 0.88 2.37 3.197(4) 157.4 8_444
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
_geom_torsion_publ_flag
C1 C1 C2 C3 11 -94.5(4) y
C1 C1 C2 C3 12 90.6(4) y
C1 C1 C2 C7 11 87.2(4) y
C1 C1 C2 C7 12 -87.7(4) y
C7 C2 C3 C4 . -0.1(4) y
C1 C2 C3 C4 . -178.5(2) y
C2 C3 C4 C5 . 0.3(4) y
C3 C4 C5 C6 . -0.1(4) y
C3 C4 C5 C8 . -178.0(2) y
C4 C5 C6 C7 . -0.4(4) y
C8 C5 C6 C7 . 177.4(2) y
C5 C6 C7 C2 . 0.7(4) y
C3 C2 C7 C6 . -0.4(4) y
C1 C2 C7 C6 . 177.9(2) y
C6 C5 C8 N2 . -168.3(2) y
C4 C5 C8 N2 . 9.5(3) y
C6 C5 C8 N1 . 10.8(3) y
C4 C5 C8 N1 . -171.4(2) y
N2 C8 N1 C10 . 0.7(4) y
C5 C8 N1 C10 . -178.4(2) y
N5 C10 N1 C8 . 179.5(2) y
N3 C10 N1 C8 . -0.4(3) y
N1 C8 N2 C9 . -0.9(4) y
C5 C8 N2 C9 . 178.1(2) y
N4 C9 N2 C8 . 179.9(2) y
N3 C9 N2 C8 . 1.0(4) y
N5 C10 N3 C9 . -179.4(2) y
N1 C10 N3 C9 . 0.5(4) y
N4 C9 N3 C10 . -179.7(2) y
N2 C9 N3 C10 . -0.9(4) y
