#------------------------------------------------------------------------------
#$Date: 2016-02-16 00:06:40 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176451 $
#$URL: svn://www.crystallography.net/cod/cif/5/00/03/5000391.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_5000391
loop_
_publ_author_name
'Lisa Barnett'
'Douglas M. Ho'
'Kim K. Baldridge'
'Robert A. Pascal'
_publ_section_title
;
The Structure of Hexabenzotriphenylene and the Problem of Overcrowded
"D3h" Polycyclic Aromatic Compounds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              727
_journal_page_last               733
_journal_paper_doi               10.1021/ja983471i
_journal_volume                  121
_journal_year                    1999
_chemical_formula_moiety
;
C42 H24
;
_chemical_formula_sum            'C42 H24'
_chemical_name_common
;
Hexabenzotriphenylene
;
_chemical_name_systematic
;
Dibenzo(f,j)phenanthro(9,10-s)picene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 103.846(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.8971(8)
_cell_length_b                   6.9274(2)
_cell_length_c                   19.4153(8)
_cell_measurement_reflns_used    57890
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.05
_cell_volume                     2598.350
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      110
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method
'oscillations; 1300 deg data in 2 deg increments'
_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  0.102
_diffrn_reflns_av_sigmaI/netI    0.0584
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            57890
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.05
_exptl_absorpt_coefficient_mu    0.077
_exptl_crystal_colour            orange.
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_preparation       nitrobenzene
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.054
_refine_ls_goodness_of_fit_obs   1.176
_refine_ls_hydrogen_treatment    'xyz refined, isotropic'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         5952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_restrained_S_obs      1.176
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_obs          0.0563
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0901P)²+0.1060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1621
_refine_ls_wR_factor_obs         0.1417
_reflns_number_observed          3809
_reflns_number_total             5952
_reflns_observed_criterion       >2sigma(I)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0901P)^2^+0.1060P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0901P)^2^+0.1060P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               5000391
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 x,1/2-y,1/2+z
3 -x,-y,-z
4 -x,-1/2+y,-1/2-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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
C1 C 0.16341(10) 0.8137(2) 0.13480(10) 0.0215(4) Uani 1 d . .
C2 C 0.18715(10) 0.6881(2) 0.08893(10) 0.0217(4) Uani 1 d . .
C3 C 0.25526(10) 0.6070(3) 0.11082(10) 0.0224(4) Uani 1 d . .
C4 C 0.30233(10) 0.6872(3) 0.16821(10) 0.0230(4) Uani 1 d . .
C5 C 0.27807(10) 0.8122(3) 0.21592(10) 0.0233(4) Uani 1 d . .
C6 C 0.21223(10) 0.8944(3) 0.19448(10) 0.0230(4) Uani 1 d . .
C7 C 0.08799(10) 0.8310(2) 0.12478(11) 0.0231(4) Uani 1 d . .
C8 C 0.05847(11) 0.8726(3) 0.18213(11) 0.0258(4) Uani 1 d . .
H8 H 0.0889(10) 0.8998(26) 0.2277(11) 0.021(5) Uiso 1 d . .
C9 C -0.01232(11) 0.8673(3) 0.17468(12) 0.0294(5) Uani 1 d . .
H9 H -0.0297(11) 0.8898(29) 0.2176(12) 0.033(6) Uiso 1 d . .
C10 C -0.05635(11) 0.8221(3) 0.10960(12) 0.0313(5) Uani 1 d . .
H10 H -0.1076(11) 0.8138(27) 0.1055(11) 0.031(6) Uiso 1 d . .
C11 C -0.02859(11) 0.7767(3) 0.05347(12) 0.0294(5) Uani 1 d . .
H11 H -0.0608(10) 0.7375(27) 0.0077(12) 0.026(5) Uiso 1 d . .
C12 C 0.04341(10) 0.7776(3) 0.05984(11) 0.0249(4) Uani 1 d . .
C13 C 0.07339(10) 0.7196(2) 0.00153(11) 0.0254(4) Uani 1 d . .
C14 C 0.03434(11) 0.7187(3) -0.06894(12) 0.0313(5) Uani 1 d . .
H14 H -0.0156(11) 0.7491(27) -0.0773(11) 0.025(5) Uiso 1 d . .
C15 C 0.06402(12) 0.6718(3) -0.12384(12) 0.0324(5) Uani 1 d . .
H15 H 0.0335(12) 0.6752(29) -0.1744(13) 0.040(6) Uiso 1 d . .
C16 C 0.13418(11) 0.6310(3) -0.10957(12) 0.0290(5) Uani 1 d . .
H16 H 0.1560(10) 0.6032(27) -0.1492(11) 0.024(5) Uiso 1 d . .
C17 C 0.17345(11) 0.6313(3) -0.04098(11) 0.0253(4) Uani 1 d . .
H17 H 0.2261(11) 0.6079(28) -0.0322(11) 0.031(6) Uiso 1 d . .
C18 C 0.14376(10) 0.6705(2) 0.01645(10) 0.0230(4) Uani 1 d . .
C19 C 0.27650(10) 0.4265(3) 0.08134(10) 0.0237(4) Uani 1 d . .
C20 C 0.22718(11) 0.2907(3) 0.04771(11) 0.0263(5) Uani 1 d . .
H20 H 0.1763(11) 0.3172(26) 0.0409(11) 0.024(5) Uiso 1 d . .
C21 C 0.24677(12) 0.1134(3) 0.02666(12) 0.0318(5) Uani 1 d . .
H21 H 0.2095(10) 0.0203(28) 0.0031(10) 0.026(5) Uiso 1 d . .
C22 C 0.31682(12) 0.0656(3) 0.03938(12) 0.0350(5) Uani 1 d . .
H22 H 0.3305(11) -0.0673(31) 0.0261(12) 0.034(6) Uiso 1 d . .
C23 C 0.36558(12) 0.1949(3) 0.07338(11) 0.0323(5) Uani 1 d . .
H23 H 0.4154(12) 0.1562(29) 0.0861(12) 0.036(6) Uiso 1 d . .
C24 C 0.34679(11) 0.3781(3) 0.09483(11) 0.0270(5) Uani 1 d . .
C25 C 0.39807(10) 0.5156(3) 0.13136(10) 0.0274(5) Uani 1 d . .
C26 C 0.46744(11) 0.5108(3) 0.12715(12) 0.0326(5) Uani 1 d . .
H26 H 0.4826(12) 0.3999(35) 0.0989(13) 0.048(7) Uiso 1 d . .
C27 C 0.51399(11) 0.6491(3) 0.15924(12) 0.0353(5) Uani 1 d . .
H27 H 0.5632(13) 0.6387(32) 0.1529(13) 0.052(7) Uiso 1 d . .
C28 C 0.49242(11) 0.7979(3) 0.19750(12) 0.0327(5) Uani 1 d . .
H28 H 0.5267(12) 0.9010(33) 0.2208(13) 0.045(7) Uiso 1 d . .
C29 C 0.42475(10) 0.8058(3) 0.20257(11) 0.0280(5) Uani 1 d . .
H29 H 0.4084(12) 0.9229(33) 0.2267(13) 0.044(6) Uiso 1 d . .
C30 C 0.37628(10) 0.6644(3) 0.17106(10) 0.0249(4) Uani 1 d . .
C31 C 0.31507(10) 0.8377(3) 0.29042(11) 0.0254(4) Uani 1 d . .
C32 C 0.36140(10) 0.6962(3) 0.32612(11) 0.0274(5) Uani 1 d . .
H32 H 0.3714(10) 0.5814(27) 0.2966(11) 0.023(5) Uiso 1 d . .
C33 C 0.39116(11) 0.7094(3) 0.39724(12) 0.0316(5) Uani 1 d . .
H33 H 0.4262(11) 0.6048(30) 0.4222(12) 0.034(6) Uiso 1 d . .
C34 C 0.37552(11) 0.8658(3) 0.43612(12) 0.0323(5) Uani 1 d . .
H34 H 0.3973(12) 0.8763(30) 0.4874(13) 0.040(6) Uiso 1 d . .
C35 C 0.32897(11) 1.0031(3) 0.40323(11) 0.0300(5) Uani 1 d . .
H35 H 0.3173(11) 1.1176(31) 0.4318(12) 0.035(6) Uiso 1 d . .
C36 C 0.29705(10) 0.9911(3) 0.33047(11) 0.0257(4) Uani 1 d . .
C37 C 0.24490(10) 1.1282(3) 0.29459(11) 0.0266(5) Uani 1 d . .
C38 C 0.23733(12) 1.3105(3) 0.32373(12) 0.0323(5) Uani 1 d . .
H38 H 0.2694(11) 1.3478(30) 0.3708(13) 0.037(6) Uiso 1 d . .
C39 C 0.18838(12) 1.4400(3) 0.28887(13) 0.0352(5) Uani 1 d . .
H39 H 0.1854(11) 1.5720(33) 0.3107(12) 0.042(6) Uiso 1 d . .
C40 C 0.14648(12) 1.3912(3) 0.22296(13) 0.0326(5) Uani 1 d . .
H40 H 0.1118(10) 1.4834(28) 0.1952(11) 0.027(5) Uiso 1 d . .
C41 C 0.15300(11) 1.2131(3) 0.19345(12) 0.0267(5) Uani 1 d . .
H41 H 0.1222(11) 1.1869(28) 0.1452(12) 0.032(6) Uiso 1 d . .
C42 C 0.20106(10) 1.0765(3) 0.22900(11) 0.0244(4) Uani 1 d . .
loop_
_atom_type_symbol
_atom_type_radius_bond
C 0.68
H 0.23
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
_geom_angle_publ_flag
C2 C1 C6 119.2(2) . . yes
C2 C1 C7 116.9(2) . . yes
C6 C1 C7 123.2(2) . . yes
C1 C2 C3 119.5(2) . . yes
C1 C2 C18 116.7(2) . . yes
C3 C2 C18 123.3(2) . . yes
C4 C3 C2 119.3(2) . . yes
C4 C3 C19 116.7(2) . . yes
C2 C3 C19 123.6(2) . . yes
C3 C4 C5 119.6(2) . . yes
C3 C4 C30 117.7(2) . . yes
C5 C4 C30 122.0(2) . . yes
C6 C5 C4 119.4(2) . . yes
C6 C5 C31 117.2(2) . . yes
C4 C5 C31 122.8(2) . . yes
C5 C6 C1 119.2(2) . . yes
C5 C6 C42 116.5(2) . . yes
C1 C6 C42 123.7(2) . . yes
C12 C7 C8 118.0(2) . . yes
C12 C7 C1 120.1(2) . . yes
C8 C7 C1 121.2(2) . . yes
C9 C8 C7 121.3(2) . . yes
C9 C8 H8 120.2(12) . . ?
C7 C8 H8 118.5(12) . . ?
C8 C9 C10 120.4(2) . . yes
C8 C9 H9 117.5(12) . . ?
C10 C9 H9 122.0(12) . . ?
C11 C10 C9 119.2(2) . . yes
C11 C10 H10 121.2(12) . . ?
C9 C10 H10 119.4(13) . . ?
C10 C11 C12 121.6(2) . . yes
C10 C11 H11 118.2(12) . . ?
C12 C11 H11 120.1(12) . . ?
C7 C12 C11 119.3(2) . . yes
C7 C12 C13 118.8(2) . . yes
C11 C12 C13 121.9(2) . . yes
C18 C13 C14 119.6(2) . . yes
C18 C13 C12 118.7(2) . . yes
C14 C13 C12 121.7(2) . . yes
C15 C14 C13 121.1(2) . . yes
C15 C14 H14 121.6(12) . . ?
C13 C14 H14 117.3(12) . . ?
C14 C15 C16 119.5(2) . . yes
C14 C15 H15 118.2(13) . . ?
C16 C15 H15 122.3(13) . . ?
C17 C16 C15 120.4(2) . . yes
C17 C16 H16 120.1(12) . . ?
C15 C16 H16 119.6(12) . . ?
C16 C17 C18 121.3(2) . . yes
C16 C17 H17 118.6(12) . . ?
C18 C17 H17 120.0(12) . . ?
C13 C18 C17 118.1(2) . . yes
C13 C18 C2 120.4(2) . . yes
C17 C18 C2 120.9(2) . . yes
C24 C19 C20 118.9(2) . . yes
C24 C19 C3 119.7(2) . . yes
C20 C19 C3 121.0(2) . . yes
C21 C20 C19 121.3(2) . . yes
C21 C20 H20 118.0(11) . . ?
C19 C20 H20 120.6(11) . . ?
C20 C21 C22 120.0(2) . . yes
C20 C21 H21 118.4(11) . . ?
C22 C21 H21 121.6(11) . . ?
C23 C22 C21 119.5(2) . . yes
C23 C22 H22 121.1(12) . . ?
C21 C22 H22 119.3(12) . . ?
C22 C23 C24 121.5(2) . . yes
C22 C23 H23 119.4(12) . . ?
C24 C23 H23 119.0(12) . . ?
C19 C24 C23 118.8(2) . . yes
C19 C24 C25 119.2(2) . . yes
C23 C24 C25 121.9(2) . . yes
C26 C25 C30 118.8(2) . . yes
C26 C25 C24 122.9(2) . . yes
C30 C25 C24 118.2(2) . . yes
C27 C26 C25 121.6(2) . . yes
C27 C26 H26 120.6(13) . . ?
C25 C26 H26 117.8(13) . . ?
C26 C27 C28 119.7(2) . . yes
C26 C27 H27 117.4(13) . . ?
C28 C27 H27 122.9(13) . . ?
C29 C28 C27 119.9(2) . . yes
C29 C28 H28 120.4(13) . . ?
C27 C28 H28 119.7(13) . . ?
C28 C29 C30 121.5(2) . . yes
C28 C29 H29 119.1(13) . . ?
C30 C29 H29 119.3(13) . . ?
C29 C30 C25 118.4(2) . . yes
C29 C30 C4 121.2(2) . . yes
C25 C30 C4 119.5(2) . . yes
C32 C31 C36 118.4(2) . . yes
C32 C31 C5 121.0(2) . . yes
C36 C31 C5 120.0(2) . . yes
C33 C32 C31 121.6(2) . . yes
C33 C32 H32 121.3(11) . . ?
C31 C32 H32 117.1(11) . . ?
C32 C33 C34 119.9(2) . . yes
C32 C33 H33 120.1(12) . . ?
C34 C33 H33 120.0(12) . . ?
C35 C34 C33 119.9(2) . . yes
C35 C34 H34 120.1(13) . . ?
C33 C34 H34 120.0(13) . . ?
C34 C35 C36 121.2(2) . . yes
C34 C35 H35 119.9(12) . . ?
C36 C35 H35 118.9(12) . . ?
C35 C36 C31 119.0(2) . . yes
C35 C36 C37 122.8(2) . . yes
C31 C36 C37 118.2(2) . . yes
C38 C37 C42 119.3(2) . . yes
C38 C37 C36 121.7(2) . . yes
C42 C37 C36 118.9(2) . . yes
C39 C38 C37 121.2(2) . . yes
C39 C38 H38 119.7(12) . . ?
C38 C39 C40 119.5(2) . . yes
C38 C39 H39 119.2(13) . . ?
C40 C39 H39 121.3(13) . . ?
C41 C40 C39 120.3(2) . . yes
C41 C40 H40 118.0(12) . . ?
C39 C40 H40 121.7(11) . . ?
C40 C41 C42 121.3(2) . . yes
C40 C41 H41 116.8(11) . . ?
C42 C41 H41 121.9(11) . . ?
C41 C42 C37 118.4(2) . . yes
C41 C42 C6 120.9(2) . . yes
C37 C42 C6 120.1(2) . . yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.406(3) . yes
C1 C6 1.435(3) . yes
C1 C7 1.471(3) . yes
C2 C3 1.434(3) . yes
C2 C18 1.469(3) . yes
C3 C4 1.388(3) . yes
C3 C19 1.479(3) . yes
C4 C5 1.434(3) . yes
C4 C30 1.468(3) . yes
C5 C6 1.397(3) . yes
C5 C31 1.468(3) . yes
C6 C42 1.471(3) . yes
C7 C12 1.406(3) . yes
C7 C8 1.407(3) . yes
C8 C9 1.382(3) . yes
C8 H8 0.96(2) . ?
C9 C10 1.390(3) . yes
C9 H9 0.99(2) . ?
C10 C11 1.371(3) . yes
C10 H10 1.00(2) . ?
C11 C12 1.408(3) . yes
C11 H11 1.00(2) . ?
C12 C13 1.457(3) . yes
C13 C18 1.402(3) . yes
C13 C14 1.402(3) . yes
C14 C15 1.375(3) . yes
C14 H14 0.99(2) . ?
C15 C16 1.386(3) . yes
C15 H15 1.02(2) . ?
C16 C17 1.373(3) . yes
C16 H16 0.99(2) . ?
C17 C18 1.407(3) . yes
C17 H17 1.03(2) . ?
C19 C24 1.400(3) . yes
C19 C20 1.403(3) . yes
C20 C21 1.380(3) . yes
C20 H20 1.01(2) . ?
C21 C22 1.396(3) . yes
C21 H21 1.01(2) . ?
C22 C23 1.368(3) . yes
C22 H22 1.01(2) . ?
C23 C24 1.414(3) . yes
C23 H23 1.00(2) . ?
C24 C25 1.451(3) . yes
C25 C26 1.402(3) . yes
C25 C30 1.416(3) . yes
C26 C27 1.374(3) . yes
C26 H26 1.03(2) . ?
C27 C28 1.397(3) . yes
C27 H27 1.02(3) . ?
C28 C29 1.374(3) . yes
C28 H28 1.02(2) . ?
C29 C30 1.407(3) . yes
C29 H29 1.03(2) . ?
C31 C32 1.409(3) . yes
C31 C36 1.412(3) . yes
C32 C33 1.369(3) . yes
C32 H32 1.03(2) . ?
C33 C34 1.398(3) . yes
C33 H33 1.04(2) . ?
C34 C35 1.374(3) . yes
C34 H34 0.99(2) . ?
C35 C36 1.406(3) . yes
C35 H35 1.03(2) . ?
C36 C37 1.455(3) . yes
C37 C38 1.407(3) . yes
C37 C42 1.407(3) . yes
C38 C39 1.377(3) . yes
C38 H38 1.02(2) . ?
C39 C40 1.391(3) . yes
C39 H39 1.02(2) . ?
C40 C41 1.380(3) . yes
C40 H40 1.00(2) . ?
C41 C42 1.403(3) . yes
C41 H41 1.01(2) . ?
