#------------------------------------------------------------------------------
#$Date: 2016-02-16 17:55:33 +0100 (mar 16 de feb de 2016) $
#$Revision: 176466 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/10/8101045.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_8101045
loop_
_publ_author_name
'Fruzinski, Andrzej'
'Karolak-Wojciechowska, Janina'
'Alibert-Franco, Sandrin'
'Santelli-Rouvier, Cristian'
'Barbe, Jaques'
_publ_section_title
;
Crystal structure of 11,12-dicyano-9,10-ethano-9,10-dihydroanthracene---
acetone (2/1), (C₃₄H₂₀N₂₀)₂ · C₃H₆O
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              471
_journal_page_last               473
_journal_volume                  216
_journal_year                    2001
_chemical_formula_moiety         'C34H20N2O * 0.5 C3H6O '
_chemical_formula_structural     'C68 H40 N40 .  C3 H6 O'
_chemical_formula_sum            'C71 H46 N4 O3'
_chemical_formula_weight         501.56
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 108.89(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.726(2)
_cell_length_b                   34.928(7)
_cell_length_c                   15.263(3)
_cell_measurement_temperature    293(2)
_cell_volume                     5410.1(18)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.232
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        ' C71 H46 N4 O3'
_cod_database_code               8101045
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O' O 0.02400(14) 0.21862(4) 0.90733(10) 0.0482(4) Uani 1 4 d . . .
C1A C 0.38014(19) 0.21896(6) 1.19504(14) 0.0426(5) Uani 1 4 d . . .
C1 C 0.3854(2) 0.20436(8) 1.28015(16) 0.0553(6) Uani 1 4 d . . .
H1 H 0.3270 0.2128 1.3097 0.083 Uiso 1 4 d R . .
C2 C 0.4797(3) 0.17661(8) 1.32105(18) 0.0642(7) Uani 1 4 d . . .
H2 H 0.4837 0.1664 1.3782 0.096 Uiso 1 4 d R . .
C3 C 0.5672(3) 0.16433(8) 1.27845(18) 0.0608(6) Uani 1 4 d . . .
H3 H 0.6297 0.1459 1.3068 0.091 Uiso 1 4 d R . .
C4 C 0.5629(2) 0.17917(7) 1.19348(17) 0.0526(6) Uani 1 4 d . . .
H4 H 0.6225 0.1709 1.1647 0.079 Uiso 1 4 d R . .
C4A C 0.46946(19) 0.20641(6) 1.15222(14) 0.0417(5) Uani 1 4 d . . .
C5 C 0.5508(3) 0.29382(8) 1.06520(18) 0.0608(6) Uani 1 4 d . . .
H5 H 0.6130 0.2854 1.0389 0.091 Uiso 1 4 d R . .
C5A C 0.4619(2) 0.26874(6) 1.08163(15) 0.0457(5) Uani 1 4 d . . .
C6 C 0.5451(3) 0.33203(9) 1.0891(2) 0.0783(9) Uani 1 4 d . . .
H6 H 0.6038 0.3494 1.0779 0.117 Uiso 1 4 d R . .
C7 C 0.4547(3) 0.34453(8) 1.1286(2) 0.0723(8) Uani 1 4 d . . .
H7 H 0.4533 0.3702 1.1442 0.108 Uiso 1 4 d R . .
C8 C 0.3655(3) 0.31923(7) 1.14556(17) 0.0588(6) Uani 1 4 d . . .
H8 H 0.3035 0.3277 1.1718 0.088 Uiso 1 4 d R . .
C8A C 0.3709(2) 0.28145(6) 1.12266(14) 0.0458(5) Uani 1 4 d . . .
C9 C 0.2856(2) 0.24922(6) 1.13927(14) 0.0442(5) Uani 1 4 d . . .
H9 H 0.2215 0.2591 1.1695 0.066 Uiso 1 4 d R . .
C10 C 0.4497(2) 0.22600(6) 1.06034(14) 0.0430(5) Uani 1 4 d . . .
H10 H 0.5210 0.2167 1.0282 0.064 Uiso 1 4 d R . .
C11 C 0.3044(2) 0.21926(6) 1.00321(14) 0.0425(5) Uani 1 4 d . . .
C12 C 0.2180(2) 0.23190(6) 1.04358(14) 0.0416(5) Uani 1 4 d . . .
C13 C 0.2776(2) 0.20124(8) 0.91577(16) 0.0533(6) Uani 1 4 d . . .
N14 N 0.2680(2) 0.18620(9) 0.84766(17) 0.0819(8) Uani 1 4 d . . .
C1'A C -0.1491(2) 0.21278(6) 1.00063(15) 0.0436(5) Uani 1 4 d . . .
C1' C -0.2120(2) 0.17967(7) 1.01263(18) 0.0551(6) Uani 1 4 d . . .
H1' H -0.1724 0.1633 1.0619 0.083 Uiso 1 4 d R . .
C2' C -0.3354(3) 0.17129(8) 0.9504(2) 0.0653(7) Uani 1 4 d . . .
H2' H -0.3793 0.1494 0.9588 0.098 Uiso 1 4 d R . .
C3' C -0.3928(2) 0.19485(9) 0.8769(2) 0.0650(7) Uani 1 4 d . . .
H3' H -0.4751 0.1887 0.8354 0.097 Uiso 1 4 d R . .
C4' C -0.3299(2) 0.22776(8) 0.86341(16) 0.0537(6) Uani 1 4 d . . .
H4' H -0.3690 0.2436 0.8130 0.081 Uiso 1 4 d R . .
C4'A C -0.2090(2) 0.23685(7) 0.92586(14) 0.0435(5) Uani 1 4 d . . .
C5'A C -0.09980(19) 0.29179(6) 1.01699(14) 0.0422(5) Uani 1 4 d . . .
C5' C -0.1259(2) 0.32945(7) 1.03227(18) 0.0566(6) Uani 1 4 d . . .
H5' H -0.1627 0.3459 0.9828 0.085 Uiso 1 4 d R . .
C6' C -0.0964(3) 0.34223(8) 1.1224(2) 0.0699(7) Uani 1 4 d . . .
H6' H -0.1138 0.3675 1.1334 0.105 Uiso 1 4 d R . .
C7' C -0.0418(3) 0.31816(8) 1.19556(19) 0.0682(7) Uani 1 4 d . . .
H7' H -0.0235 0.3271 1.2558 0.102 Uiso 1 4 d R . .
C8' C -0.0142(2) 0.28072(8) 1.18051(16) 0.0544(6) Uani 1 4 d . . .
H8' H 0.0229 0.2645 1.2304 0.082 Uiso 1 4 d R . .
C8'A C -0.04131(19) 0.26754(6) 1.09149(14) 0.0416(5) Uani 1 4 d . . .
C9' C -0.0175(2) 0.22708(6) 1.06226(14) 0.0416(5) Uani 1 4 d . . .
H9' H 0.0411 0.2087 1.1176 0.062 Uiso 1 4 d R . .
C10' C -0.1292(2) 0.27220(6) 0.92406(14) 0.0436(5) Uani 1 4 d . . .
H10' H -0.1591 0.2894 0.8716 0.065 Uiso 1 4 d R . .
C11' C 0.0067(2) 0.25855(6) 0.92341(14) 0.0442(5) Uani 1 4 d . . .
C12' C 0.07314(19) 0.23282(6) 1.00157(14) 0.0407(5) Uani 1 4 d . . .
C13' C 0.0832(2) 0.28482(7) 0.88855(17) 0.0552(6) Uani 1 4 d . . .
N14' N 0.1388(3) 0.30666(8) 0.8604(2) 0.0906(9) Uani 1 4 d . . .
O" O 0.94999(17) 0.08311(5) 0.12357(12) 0.0606(4) Uani 1 4 d . . .
C1*A C 0.8095(2) 0.03559(7) 0.35577(16) 0.0526(6) Uani 1 4 d . . .
C1* C 0.8589(3) 0.04951(8) 0.44455(19) 0.0722(8) Uani 1 4 d . . .
H1* H 0.9471 0.0461 0.4792 0.108 Uiso 1 4 d R . .
C2* C 0.7736(5) 0.06867(9) 0.4817(3) 0.0933(12) Uani 1 4 d . . .
H2* H 0.8058 0.0783 0.5417 0.140 Uiso 1 4 d R . .
C3* C 0.6451(5) 0.07362(9) 0.4320(3) 0.0931(11) Uani 1 4 d . . .
H3* H 0.5901 0.0864 0.4585 0.140 Uiso 1 4 d R . .
C4* C 0.5945(3) 0.05993(8) 0.3426(3) 0.0790(9) Uani 1 4 d . . .
H4* H 0.5059 0.0633 0.3088 0.119 Uiso 1 4 d R . .
C4*A C 0.6782(2) 0.04106(7) 0.30424(18) 0.0555(6) Uani 1 4 d . . .
C5*A C 0.6811(3) -0.01811(8) 0.22096(17) 0.0587(6) Uani 1 4 d . . .
C5* C 0.6001(3) -0.04901(9) 0.1866(2) 0.0770(8) Uani 1 4 d . . .
H5* H 0.5124 -0.0453 0.1512 0.116 Uiso 1 4 d R . .
C6* C 0.6508(5) -0.08548(10) 0.2051(3) 0.0936(11) Uani 1 4 d . . .
H6* H 0.5968 -0.1064 0.1819 0.140 Uiso 1 4 d R . .
C7* C 0.7811(4) -0.09115(9) 0.2577(3) 0.0917(11) Uani 1 4 d . . .
H7* H 0.8143 -0.1159 0.2699 0.138 Uiso 1 4 d R . .
C8* C 0.8613(3) -0.06004(8) 0.2918(2) 0.0740(8) Uani 1 4 d . . .
H8* H 0.9488 -0.0638 0.3277 0.111 Uiso 1 4 d R . .
C8*A C 0.8120(2) -0.02366(7) 0.27316(17) 0.0544(6) Uani 1 4 d . . .
C9* C 0.8855(2) 0.01385(7) 0.30364(16) 0.0511(6) Uani 1 4 d . . .
H9* H 0.9797 0.0129 0.3395 0.077 Uiso 1 4 d R . .
C10* C 0.6442(2) 0.02405(8) 0.20758(18) 0.0585(6) Uani 1 4 d . . .
H10* H 0.5405 0.0283 0.1728 0.088 Uiso 1 4 d R . .
C11* C 0.7423(2) 0.04204(7) 0.16568(16) 0.0559(6) Uani 1 4 d . . .
C12* C 0.8688(2) 0.03747(7) 0.21606(15) 0.0500(5) Uani 1 4 d . . .
C13* C 0.6922(3) 0.06199(9) 0.0807(2) 0.0758(9) Uani 1 4 d . . .
N14* N 0.6411(3) 0.07619(11) 0.0113(2) 0.1214(13) Uani 1 4 d . . .
C1"A C 1.2187(2) 0.08007(7) 0.33288(17) 0.0516(6) Uani 1 4 d . . .
C1" C 1.2847(3) 0.09260(8) 0.42116(19) 0.0676(7) Uani 1 4 d . . .
H1" H 1.2987 0.1186 0.4337 0.101 Uiso 1 4 d R . .
C2" C 1.3293(4) 0.06577(10) 0.4914(2) 0.0860(10) Uani 1 4 d . . .
H2" H 1.3737 0.0739 0.5514 0.129 Uiso 1 4 d R . .
C3" C 1.3106(3) 0.02744(9) 0.4731(2) 0.0814(9) Uani 1 4 d . . .
H3" H 1.3427 0.0098 0.5207 0.122 Uiso 1 4 d R . .
C4" C 1.2437(3) 0.01486(8) 0.3849(2) 0.0646(7) Uani 1 4 d . . .
H4" H 1.2316 -0.0112 0.3728 0.097 Uiso 1 4 d R . .
C4"A C 1.1946(2) 0.04101(7) 0.31480(17) 0.0506(5) Uani 1 4 d . . .
C5"A C 1.1859(2) 0.05030(8) 0.15570(18) 0.0578(6) Uani 1 4 d . . .
C5" C 1.2249(3) 0.03178(10) 0.0889(2) 0.0765(8) Uani 1 4 d . . .
H5" H 1.2075 0.0059 0.0768 0.115 Uiso 1 4 d R . .
C6" C 1.2911(4) 0.05286(14) 0.0402(2) 0.0945(11) Uani 1 4 d . . .
H6" H 1.3178 0.0409 -0.0051 0.142 Uiso 1 4 d R . .
C7" C 1.3172(3) 0.09083(13) 0.0580(3) 0.0924(10) Uani 1 4 d . . .
H7" H 1.3621 0.1043 0.0250 0.139 Uiso 1 4 d R . .
C8" C 1.2783(3) 0.10943(9) 0.1239(2) 0.0711(8) Uani 1 4 d . . .
H8" H 1.2959 0.1354 0.1353 0.107 Uiso 1 4 d R . .
C8"A C 1.2127(2) 0.08899(7) 0.17339(17) 0.0555(6) Uani 1 4 d . . .
C9" C 1.1626(2) 0.10485(7) 0.24737(17) 0.0512(5) Uani 1 4 d . . .
H9" H 1.2017 0.1343 0.2609 0.077 Uiso 1 4 d R . .
C10" C 1.1140(2) 0.03228(7) 0.21552(17) 0.0521(6) Uani 1 4 d . . .
H10" H 1.0806 0.0025 0.2044 0.078 Uiso 1 4 d R . .
C11" C 1.0135(2) 0.09640(7) 0.21680(17) 0.0507(5) Uani 1 4 d . . .
C12" C 0.9835(2) 0.05530(7) 0.19863(16) 0.0494(5) Uani 1 4 d . . .
C13" C 0.9329(2) 0.12043(8) 0.25296(19) 0.0600(6) Uani 1 4 d . . .
N14" N 0.8710(3) 0.14003(8) 0.2819(2) 0.0927(9) Uani 1 4 d . . .
C2R C 0.8534(4) 0.08636(10) 0.8104(3) 0.0920(11) Uani 1 4 d . . .
O2R O 0.8620(4) 0.06854(11) 0.7460(3) 0.1560(14) Uani 1 4 d . . .
C3R C 0.7295(9) 0.1017(3) 0.8017(6) 0.264(5) Uani 1 4 d . . .
H3RA H 0.6621 0.0857 0.7617 0.397 Uiso 1 4 d R . .
H3RB H 0.7228 0.1270 0.7758 0.397 Uiso 1 4 d R . .
H3RC H 0.7185 0.1030 0.8616 0.397 Uiso 1 4 d R . .
C1R C 0.9583(8) 0.0981(3) 0.8911(4) 0.238(4) Uani 1 4 d . . .
H1RA H 1.0206 0.0776 0.9113 0.357 Uiso 1 4 d R . .
H1RB H 0.9230 0.1045 0.9395 0.357 Uiso 1 4 d R . .
H1RC H 1.0015 0.1201 0.8765 0.357 Uiso 1 4 d R . .
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
O' C11' 1.439(3) . ?
O' C12' 1.450(2) . ?
C1A C1 1.380(3) . ?
C1A C4A 1.394(3) . ?
C1A C9 1.520(3) . ?
C1 C2 1.394(4) . ?
C1 H1 0.9299 . ?
C2 C3 1.372(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C4A 1.378(3) . ?
C4 H4 0.9300 . ?
C4A C10 1.512(3) . ?
C5 C5A 1.376(3) . ?
C5 C6 1.390(4) . ?
C5 H5 0.9301 . ?
C5A C8A 1.392(3) . ?
C5A C10 1.525(3) . ?
C6 C7 1.368(5) . ?
C6 H6 0.9299 . ?
C7 C8 1.387(4) . ?
C7 H7 0.9301 . ?
C8 C8A 1.371(3) . ?
C8 H8 0.9300 . ?
C8A C9 1.523(3) . ?
C9 C12 1.529(3) . ?
C9 H9 1.0053 . ?
C10 C11 1.537(3) . ?
C10 H10 1.0833 . ?
C11 C12 1.343(3) . ?
C11 C13 1.418(3) . ?
C12 C12' 1.477(3) . ?
C13 N14 1.139(3) . ?
C1'A C1' 1.380(3) . ?
C1'A C4'A 1.395(3) . ?
C1'A C9' 1.506(3) . ?
C1' C2' 1.387(4) . ?
C1' H1' 0.9301 . ?
C2' C3' 1.367(4) . ?
C2' H2' 0.9300 . ?
C3' C4' 1.381(4) . ?
C3' H3' 0.9300 . ?
C4' C4'A 1.375(3) . ?
C4' H4' 0.9300 . ?
C4'A C10' 1.508(3) . ?
C5'A C5' 1.380(3) . ?
C5'A C8'A 1.393(3) . ?
C5'A C10' 1.513(3) . ?
C5' C6' 1.381(4) . ?
C5' H5' 0.9299 . ?
C6' C7' 1.369(4) . ?
C6' H6' 0.9302 . ?
C7' C8' 1.377(4) . ?
C7' H7' 0.9300 . ?
C8' C8'A 1.374(3) . ?
C8' H8' 0.9299 . ?
C8'A C9' 1.528(3) . ?
C9' C12' 1.558(3) . ?
C9' H9' 1.0848 . ?
C10' C11' 1.536(3) . ?
C10' H10' 0.9697 . ?
C11' C13' 1.443(3) . ?
C11' C12' 1.479(3) . ?
C13' N14' 1.135(3) . ?
O" C11" 1.441(3) . ?
O" C12" 1.455(3) . ?
C1*A C1* 1.374(4) . ?
C1*A C4*A 1.386(3) . ?
C1*A C9* 1.514(4) . ?
C1* C2* 1.394(5) . ?
C1* H1* 0.9300 . ?
C2* C3* 1.352(6) . ?
C2* H2* 0.9299 . ?
C3* C4* 1.381(5) . ?
C3* H3* 0.9299 . ?
C4* C4*A 1.387(4) . ?
C4* H4* 0.9300 . ?
C4*A C10* 1.521(4) . ?
C5*A C5* 1.378(4) . ?
C5*A C8*A 1.385(4) . ?
C5*A C10* 1.521(4) . ?
C5* C6* 1.378(5) . ?
C5* H5* 0.9300 . ?
C6* C7* 1.382(6) . ?
C6* H6* 0.9299 . ?
C7* C8* 1.379(5) . ?
C7* H7* 0.9298 . ?
C8* C8*A 1.370(4) . ?
C8* H8* 0.9300 . ?
C8*A C9* 1.522(3) . ?
C9* C12* 1.531(3) . ?
C9* H9* 0.9815 . ?
C10* C11* 1.532(3) . ?
C10* H10* 1.0762 . ?
C11* C12* 1.334(3) . ?
C11* C13* 1.416(4) . ?
C12* C12" 1.479(3) . ?
C13* N14* 1.137(4) . ?
C1"A C1" 1.375(4) . ?
C1"A C4"A 1.399(3) . ?
C1"A C9" 1.519(3) . ?
C1" C2" 1.387(4) . ?
C1" H1" 0.9302 . ?
C2" C3" 1.369(4) . ?
C2" H2" 0.9301 . ?
C3" C4" 1.377(4) . ?
C3" H3" 0.9299 . ?
C4" C4"A 1.375(4) . ?
C4" H4" 0.9298 . ?
C4"A C10" 1.513(3) . ?
C5"A C5" 1.382(4) . ?
C5"A C8"A 1.390(4) . ?
C5"A C10" 1.510(3) . ?
C5" C6" 1.393(5) . ?
C5" H5" 0.9302 . ?
C6" C7" 1.364(5) . ?
C6" H6" 0.9298 . ?
C7" C8" 1.370(5) . ?
C7" H7" 0.9300 . ?
C8" C8"A 1.386(4) . ?
C8" H8" 0.9297 . ?
C8"A C9" 1.505(3) . ?
C9" C11" 1.543(3) . ?
C9" H9" 1.1032 . ?
C10" C12" 1.562(3) . ?
C10" H10" 1.0965 . ?
C11" C13" 1.437(4) . ?
C11" C12" 1.477(3) . ?
C13" N14" 1.137(3) . ?
C2R O2R 1.191(4) . ?
C2R C3R 1.399(7) . ?
C2R C1R 1.434(8) . ?
C3R H3RA 0.9600 . ?
C3R H3RB 0.9600 . ?
C3R H3RC 0.9600 . ?
C1R H1RA 0.9600 . ?
C1R H1RB 0.9600 . ?
C1R H1RC 0.9600 . ?
