#------------------------------------------------------------------------------
#$Date: 2016-03-21 16:50:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178756 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/10/4101054.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_4101054
loop_
_publ_author_name
'Ilhan, Faysal'
'Tyson, Daniel'
'Stasko, Daniel'
'Kirschbaum, Kristin'
'Meador, Micheal A.'
_publ_section_title
;
Twisted, Z-Shaped Perylene Bisimide
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_year                    2006
_chemical_formula_moiety         'C52 H50 N2 O4'
_chemical_formula_sum            'C52 H50 N2 O4'
_chemical_formula_weight         766.94
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 93.089(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.0080(12)
_cell_length_b                   8.2920(5)
_cell_length_c                   22.3830(12)
_cell_measurement_temperature    150(1)
_cell_volume                     4078.7(4)
_diffrn_ambient_temperature      150(1)
_exptl_crystal_density_diffrn    1.249
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4101054
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
O1 O 0.82721(7) 0.6521(2) 0.32266(7) 0.0464(4) Uani 1 1 d . A .
O2 O 0.74208(7) 0.6095(3) 0.13416(8) 0.0573(5) Uani 1 1 d . A .
N1 N 0.77226(8) 0.6343(2) 0.23318(8) 0.0374(5) Uani 1 1 d . A .
C1 C 1.06856(10) 0.4540(3) 0.14980(9) 0.0332(5) Uani 1 1 d . A .
C2 C 1.04068(10) 0.4393(3) 0.09241(10) 0.0378(5) Uani 1 1 d . . .
C3 C 0.97990(10) 0.4675(3) 0.08316(10) 0.0379(5) Uani 1 1 d . . .
C4 C 0.94333(9) 0.5011(3) 0.13162(9) 0.0328(5) Uani 1 1 d . A .
C5 C 0.87922(10) 0.5301(3) 0.12188(10) 0.0353(5) Uani 1 1 d . . .
C6 C 0.84728(9) 0.5620(3) 0.17126(10) 0.0343(5) Uani 1 1 d . A .
C7 C 0.78151(10) 0.6029(3) 0.17375(10) 0.0395(6) Uani 1 1 d . . .
C8 C 0.82497(10) 0.6178(3) 0.27000(10) 0.0347(5) Uani 1 1 d . . .
C9 C 0.87361(9) 0.5615(2) 0.23048(9) 0.0311(5) Uani 1 1 d . A .
C10 C 0.93479(9) 0.5253(2) 0.24197(9) 0.0289(5) Uani 1 1 d . . .
C11 C 0.97104(9) 0.5078(2) 0.19077(9) 0.0292(5) Uani 1 1 d . A .
C12 C 1.03560(9) 0.4954(2) 0.19843(9) 0.0295(5) Uani 1 1 d . . .
C13A C 0.8493(2) 0.5528(7) 0.0627(2) 0.0216(13) Uiso 0.50 1 d P A 1
C14A C 0.8205(3) 0.4150(7) 0.0357(3) 0.0479(14) Uiso 0.50 1 d P A 1
H14A H 0.8195 0.3160 0.0569 0.057 Uiso 0.50 1 calc PR A 1
C15A C 0.7940(3) 0.4261(8) -0.0219(3) 0.0523(15) Uiso 0.50 1 d P A 1
H15A H 0.7751 0.3344 -0.0403 0.063 Uiso 0.50 1 calc PR A 1
C16A C 0.7952(2) 0.5726(7) -0.0528(2) 0.0252(10) Uiso 0.50 1 d P A 1
H16A H 0.7798 0.5791 -0.0931 0.030 Uiso 0.50 1 calc PR A 1
C17A C 0.8193(2) 0.7094(7) -0.0238(2) 0.0309(12) Uiso 0.50 1 d P A 1
H17A H 0.8168 0.8112 -0.0432 0.037 Uiso 0.50 1 calc PR A 1
C18A C 0.8462(3) 0.6977(8) 0.0318(3) 0.0374(17) Uiso 0.50 1 d P A 1
H18A H 0.8635 0.7916 0.0502 0.045 Uiso 0.50 1 calc PR A 1
C13B C 0.8509(3) 0.5079(8) 0.0573(3) 0.0350(17) Uiso 0.50 1 d P A 3
C14B C 0.8406(3) 0.3767(7) 0.0274(2) 0.0464(14) Uiso 0.50 1 d P A 3
H14B H 0.8522 0.2762 0.0449 0.056 Uiso 0.50 1 calc PR A 3
C15B C 0.8131(3) 0.3793(9) -0.0297(3) 0.0603(17) Uiso 0.50 1 d P A 3
H15B H 0.8066 0.2804 -0.0505 0.072 Uiso 0.50 1 calc PR A 3
C16B C 0.7965(3) 0.5082(9) -0.0548(3) 0.0529(17) Uiso 0.50 1 d P A 3
H16B H 0.7737 0.5043 -0.0920 0.064 Uiso 0.50 1 calc PR A 3
C17B C 0.8104(3) 0.6513(10) -0.0301(3) 0.0499(16) Uiso 0.50 1 d P A 3
H17B H 0.8013 0.7486 -0.0512 0.060 Uiso 0.50 1 calc PR A 3
C18B C 0.8393(3) 0.6549(10) 0.0292(3) 0.050(2) Uiso 0.50 1 d P A 3
H18B H 0.8500 0.7540 0.0483 0.060 Uiso 0.50 1 calc PR A 3
C19 C 0.71425(10) 0.6870(3) 0.25527(13) 0.0422(6) Uani 1 1 d . . .
C20 C 0.67508(11) 0.5478(3) 0.27412(12) 0.0423(6) Uani 1 1 d . A .
C21 C 0.61620(12) 0.6078(3) 0.29876(14) 0.0468(6) Uani 1 1 d . . .
C22 C 0.57488(13) 0.4770(3) 0.32028(15) 0.0639(8) Uani 1 1 d . A .
H22A H 0.5982 0.4087 0.3497 0.077 Uiso 1 1 calc R . .
H22B H 0.5617 0.4079 0.2859 0.077 Uiso 1 1 calc R . .
C23 C 0.51872(14) 0.5416(4) 0.34912(18) 0.0636(8) Uani 1 1 d . . .
C24A C 0.4676(3) 0.4097(7) 0.3562(3) 0.0515(13) Uiso 0.50 1 d P A 1
H24A H 0.4527 0.3738 0.3158 0.062 Uiso 0.50 1 calc PR A 1
H24B H 0.4860 0.3151 0.3772 0.062 Uiso 0.50 1 calc PR A 1
C25A C 0.4145(3) 0.4659(8) 0.3895(3) 0.0598(16) Uiso 0.50 1 d P A 1
H25A H 0.3802 0.3896 0.3831 0.072 Uiso 0.50 1 calc PR A 1
H25B H 0.4011 0.5732 0.3746 0.072 Uiso 0.50 1 calc PR A 1
C26A C 0.4334(4) 0.4763(11) 0.4569(4) 0.097(2) Uiso 0.50 1 d P A 1
H26A H 0.3990 0.5155 0.4789 0.145 Uiso 0.50 1 calc PR A 1
H26B H 0.4677 0.5509 0.4629 0.145 Uiso 0.50 1 calc PR A 1
H26C H 0.4454 0.3692 0.4718 0.145 Uiso 0.50 1 calc PR A 1
C24B C 0.4864(3) 0.4254(7) 0.3865(3) 0.0598(15) Uiso 0.50 1 d P A 3
H24C H 0.5149 0.3855 0.4189 0.072 Uiso 0.50 1 calc PR A 3
H24D H 0.4733 0.3318 0.3615 0.072 Uiso 0.50 1 calc PR A 3
C25B C 0.4294(3) 0.5000(9) 0.4149(4) 0.0720(19) Uiso 0.50 1 d P A 3
H25D H 0.4429 0.5879 0.4424 0.086 Uiso 0.50 1 calc PR A 3
H25E H 0.4025 0.5479 0.3828 0.086 Uiso 0.50 1 calc PR A 3
C26B C 0.3942(3) 0.3810(9) 0.4482(3) 0.084(2) Uiso 0.50 1 d P A 3
H26D H 0.3588 0.4341 0.4642 0.126 Uiso 0.50 1 calc PR A 3
H26E H 0.4201 0.3364 0.4811 0.126 Uiso 0.50 1 calc PR A 3
H26F H 0.3805 0.2938 0.4211 0.126 Uiso 0.50 1 calc PR A 3
H1 H 1.1118(11) 0.436(3) 0.1563(9) 0.031(6) Uiso 1 1 d . . .
H3 H 0.9615(11) 0.458(3) 0.0445(11) 0.041(6) Uiso 1 1 d . . .
H20B H 0.6643(12) 0.482(3) 0.2378(12) 0.055(8) Uiso 1 1 d . . .
H2 H 1.0643(11) 0.407(3) 0.0593(11) 0.044(6) Uiso 1 1 d . . .
H19B H 0.7248(11) 0.750(3) 0.2912(12) 0.050(7) Uiso 1 1 d . . .
H19A H 0.6934(12) 0.748(3) 0.2225(12) 0.053(7) Uiso 1 1 d . . .
H21B H 0.5950(14) 0.669(4) 0.2685(13) 0.070(9) Uiso 1 1 d . . .
H20A H 0.6989(12) 0.484(3) 0.3062(12) 0.055(7) Uiso 1 1 d . . .
H21A H 0.6289(14) 0.677(4) 0.3305(14) 0.073(10) Uiso 1 1 d . . .
H23B H 0.4953(17) 0.614(5) 0.3185(16) 0.097(12) Uiso 1 1 d . . .
H23A H 0.5348(15) 0.603(4) 0.3844(15) 0.077(10) Uiso 1 1 d . . .
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
O1 C8 1.211(3) . ?
O2 C7 1.208(3) . ?
N1 C7 1.381(3) . ?
N1 C8 1.393(3) . ?
N1 C19 1.460(3) . ?
C1 C12 1.383(3) . ?
C1 C2 1.399(3) . ?
C1 H1 0.97(2) . ?
C2 C3 1.363(3) . ?
C2 H2 0.96(3) . ?
C3 C4 1.413(3) . ?
C3 H3 0.94(2) . ?
C4 C11 1.429(3) . ?
C4 C5 1.436(3) . ?
C5 C6 1.367(3) . ?
C5 C13A 1.459(5) . ?
C5 C13B 1.555(6) . ?
C6 C9 1.418(3) . ?
C6 C7 1.491(3) . ?
C8 C9 1.499(3) . ?
C9 C10 1.390(3) . ?
C10 C11 1.439(3) . ?
C10 C12 1.474(3) 2_755 ?
C11 C12 1.426(3) . ?
C12 C10 1.474(3) 2_755 ?
C13A C18A 1.386(8) . ?
C13A C14A 1.426(8) . ?
C14A C15A 1.389(8) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.398(8) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.397(7) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.352(8) . ?
C17A H17A 0.9500 . ?
C18A H18A 0.9500 . ?
C13B C14B 1.291(9) . ?
C13B C18B 1.389(10) . ?
C14B C15B 1.384(8) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.252(10) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.337(10) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.439(10) . ?
C17B H17B 0.9500 . ?
C18B H18B 0.9500 . ?
C19 C20 1.514(3) . ?
C19 H19B 0.98(3) . ?
C19 H19A 0.98(3) . ?
C20 C21 1.519(3) . ?
C20 H20B 1.00(3) . ?
C20 H20A 1.02(3) . ?
C21 C22 1.511(4) . ?
C21 H21B 0.95(3) . ?
C21 H21A 0.94(3) . ?
C22 C23 1.522(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24B 1.483(7) . ?
C23 C24A 1.583(6) . ?
C23 H23B 1.03(4) . ?
C23 H23A 0.99(3) . ?
C24A C25A 1.494(8) . ?
C24A H24A 0.9900 . ?
C24A H24B 0.9900 . ?
C25A C26A 1.546(10) . ?
C25A H25A 0.9900 . ?
C25A H25B 0.9900 . ?
C26A H26A 0.9800 . ?
C26A H26B 0.9800 . ?
C26A H26C 0.9800 . ?
C24B C25B 1.563(9) . ?
C24B H24C 0.9900 . ?
C24B H24D 0.9900 . ?
C25B C26B 1.480(10) . ?
C25B H25D 0.9900 . ?
C25B H25E 0.9900 . ?
C26B H26D 0.9800 . ?
C26B H26E 0.9800 . ?
C26B H26F 0.9800 . ?
