data_7051212
_journal_name_full  'New Journal of Chemistry'
_journal_year      2001
_journal_volume  25
_journal_page_first  1553
_publ_section_title
;
Design and synthesis of 4,4'-p-conjugated-[2,2']-bipyridines : a
versatile class of tuneable chromophores and fluorophores
;
loop_
_publ_author_name
'Olivier Maury'
'Jean-Paul Guegan'
'Thierry Renouard'
'Adam Hilton'
'Philippe Dupau'
'Nicolas Sandon'
'L. Toupet'
'H.Le Bozec'
_chemical_formula_sum  'C84 H108 N8'
_chemical_formula_weight  1229.78
_symmetry_cell_setting  Triclinic
_symmetry_space_group_name_H-M  'P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
_cell_length_a  11.915(3)
_cell_length_b  12.050(4)
_cell_length_c  13.544(2)
_cell_angle_alpha  105.67(2)
_cell_angle_beta  99.141(10)
_cell_angle_gamma  93.40(2)
_cell_volume  1837.9(8)
_cell_formula_units_Z  1
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.111
_diffrn_ambient_temperature  293(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
N1 N -0.3362(8) -0.9048(6) -0.1752(7) 0.068(2) Uani 1 1 d . . .
N2 N 0.3608(8) -0.2186(8) 0.1910(8) 0.082(3) Uani 1 1 d . . .
N3 N -0.4747(7) -0.6483(8) -0.0914(8) 0.078(3) Uani 1 1 d . . .
N4 N -1.1704(7) -1.3267(7) -0.4557(7) 0.076(3) Uani 1 1 d . . .
N51 N -0.3340(8) -0.3921(8) -0.1964(7) 0.076(3) Uani 1 1 d . . .
N52 N 0.3436(8) 0.2870(8) 0.2203(7) 0.082(3) Uani 1 1 d . . .
N53 N -0.4755(7) -0.1549(6) -0.0665(7) 0.068(2) Uani 1 1 d . . .
N54 N -1.1505(9) -0.8355(8) -0.4854(8) 0.085(3) Uani 1 1 d . . .
C2 C -0.3451(9) -0.7896(9) -0.1346(8) 0.064(3) Uani 1 1 d . . .
C3 C -0.2519(9) -0.7053(8) -0.0853(8) 0.063(3) Uani 1 1 d . . .
H3 H -0.2635 -0.6290 -0.0542 0.076 Uiso 1 1 calc R . .
C4 C -0.1424(9) -0.7381(9) -0.0840(7) 0.065(3) Uani 1 1 d . . .
C5 C -0.1354(9) -0.8579(9) -0.1257(8) 0.074(3) Uani 1 1 d . . .
H5 H -0.0648 -0.8869 -0.1210 0.089 Uiso 1 1 calc R . .
C6 C -0.2319(10) -0.9303(9) -0.1726(8) 0.075(3) Uani 1 1 d . . .
H6 H -0.2222 -1.0063 -0.2065 0.089 Uiso 1 1 calc R . .
C7 C -0.0372(9) -0.6611(9) -0.0361(7) 0.069(3) Uani 1 1 d . . .
H7 H 0.0299 -0.6947 -0.0232 0.083 Uiso 1 1 calc R . .
C8 C -0.0313(9) -0.5476(10) -0.0102(8) 0.073(3) Uani 1 1 d . . .
H8 H -0.0993 -0.5158 -0.0239 0.088 Uiso 1 1 calc R . .
C9 C 0.0720(8) -0.4649(9) 0.0385(8) 0.065(3) Uani 1 1 d . . .
C10 C 0.1790(11) -0.4993(9) 0.0606(9) 0.074(3) Uani 1 1 d . . .
H10 H 0.1883 -0.5779 0.0421 0.088 Uiso 1 1 calc R . .
C11 C 0.2743(11) -0.4182(11) 0.1104(8) 0.090(4) Uani 1 1 d . . .
H11 H 0.3444 -0.4456 0.1258 0.108 Uiso 1 1 calc R . .
C12 C 0.2694(9) -0.2991(9) 0.1380(8) 0.067(3) Uani 1 1 d . . .
C13 C 0.1584(8) -0.2658(9) 0.1088(8) 0.066(3) Uani 1 1 d . . .
H13 H 0.1496 -0.1874 0.1209 0.080 Uiso 1 1 calc R . .
C14 C 0.0637(9) -0.3461(9) 0.0631(9) 0.071(3) Uani 1 1 d . . .
H14 H -0.0073 -0.3201 0.0484 0.085 Uiso 1 1 calc R . .
C15 C 0.4704(10) -0.2578(10) 0.2263(8) 0.081(3) Uani 1 1 d . . .
H15A H 0.4559 -0.3239 0.2523 0.097 Uiso 1 1 calc R . .
H15B H 0.5144 -0.1962 0.2836 0.097 Uiso 1 1 calc R . .
C16 C 0.5413(8) -0.2922(9) 0.1398(9) 0.069(3) Uani 1 1 d . . .
H16A H 0.5671 -0.2242 0.1207 0.083 Uiso 1 1 calc R . .
H16B H 0.4952 -0.3467 0.0784 0.083 Uiso 1 1 calc R . .
C17 C 0.6434(12) -0.3475(12) 0.1806(13) 0.116(5) Uani 1 1 d . . .
H17A H 0.6173 -0.4176 0.1962 0.139 Uiso 1 1 calc R . .
H17B H 0.6868 -0.2944 0.2442 0.139 Uiso 1 1 calc R . .
C18 C 0.7195(13) -0.3767(13) 0.0974(10) 0.118(5) Uani 1 1 d . . .
H18A H 0.7872 -0.4058 0.1249 0.141 Uiso 1 1 calc R . .
H18B H 0.7404 -0.3081 0.0786 0.141 Uiso 1 1 calc R . .
H18C H 0.6783 -0.4345 0.0369 0.141 Uiso 1 1 calc R . .
C19 C 0.3518(12) -0.0943(10) 0.2130(10) 0.098(4) Uani 1 1 d D . .
H19A H 0.2966 -0.0809 0.1577 0.117 Uiso 1 1 calc R . .
H19B H 0.4252 -0.0553 0.2125 0.117 Uiso 1 1 calc R . .
C20 C 0.315(2) -0.0392(18) 0.3206(11) 0.238(14) Uani 1 1 d D . .
H20A H 0.2383 -0.0801 0.2977 0.286 Uiso 1 1 calc R . .
H20B H 0.3564 -0.0896 0.3545 0.286 Uiso 1 1 calc R . .
C21 C 0.299(3) 0.001(3) 0.3763(15) 0.34(2) Uani 1 1 d . . .
H21A H 0.2321 0.0266 0.3417 0.413 Uiso 1 1 calc R . .
H21B H 0.3587 0.0629 0.3840 0.413 Uiso 1 1 calc R . .
C22 C 0.2754(16) 0.0477(15) 0.4744(15) 0.169(8) Uani 1 1 d . . .
H22A H 0.2084 0.0878 0.4692 0.203 Uiso 1 1 calc R . .
H22B H 0.3389 0.1012 0.5167 0.203 Uiso 1 1 calc R . .
H22C H 0.2622 -0.0132 0.5058 0.203 Uiso 1 1 calc R . .
C32 C -0.4638(10) -0.7568(7) -0.1374(7) 0.063(3) Uani 1 1 d . . .
C33 C -0.5580(10) -0.8368(10) -0.1755(8) 0.073(3) Uani 1 1 d . . .
H33 H -0.5479 -0.9150 -0.1971 0.088 Uiso 1 1 calc R . .
C34 C -0.6695(8) -0.8037(9) -0.1829(8) 0.066(3) Uani 1 1 d . . .
C35 C -0.6805(10) -0.6882(9) -0.1356(9) 0.077(3) Uani 1 1 d . . .
H35 H -0.7524 -0.6628 -0.1320 0.092 Uiso 1 1 calc R . .
C36 C -0.5827(11) -0.6117(9) -0.0940(10) 0.086(4) Uani 1 1 d . . .
H36 H -0.5896 -0.5333 -0.0670 0.103 Uiso 1 1 calc R . .
C37 C -0.7730(10) -0.8863(10) -0.2272(9) 0.080(3) Uani 1 1 d . . .
H37 H -0.8413 -0.8534 -0.2355 0.096 Uiso 1 1 calc R . .
C38 C -0.7818(9) -0.9994(8) -0.2563(8) 0.070(3) Uani 1 1 d . . .
H38 H -0.7139 -1.0320 -0.2447 0.083 Uiso 1 1 calc R . .
C39 C -0.8828(9) -1.0817(9) -0.3045(8) 0.068(3) Uani 1 1 d . . .
C40 C -0.8802(10) -1.2014(10) -0.3281(8) 0.076(3) Uani 1 1 d . . .
H40 H -0.8111 -1.2281 -0.3077 0.092 Uiso 1 1 calc R . .
C41 C -0.9693(9) -1.2818(10) -0.3782(9) 0.077(3) Uani 1 1 d . . .
H41 H -0.9587 -1.3601 -0.3947 0.092 Uiso 1 1 calc R . .
C42 C -1.0745(9) -1.2492(9) -0.4045(8) 0.067(3) Uani 1 1 d . . .
C43 C -1.0868(7) -1.1292(8) -0.3787(9) 0.072(3) Uani 1 1 d . . .
H43 H -1.1586 -1.1042 -0.3915 0.087 Uiso 1 1 calc R . .
C44 C -0.9928(9) -1.0500(9) -0.3347(9) 0.076(3) Uani 1 1 d . . .
H44 H -1.0016 -0.9718 -0.3243 0.091 Uiso 1 1 calc R . .
C45 C -1.1697(10) -1.4493(10) -0.4801(9) 0.092(4) Uani 1 1 d . . .
H45A H -1.2421 -1.4814 -0.4698 0.110 Uiso 1 1 calc R . .
H45B H -1.1104 -1.4652 -0.4293 0.110 Uiso 1 1 calc R . .
C46 C -1.152(3) -1.5114(19) -0.580(2) 0.257(15) Uani 1 1 d . . .
H46A H -1.1064 -1.5702 -0.5645 0.308 Uiso 1 1 calc R . .
H46B H -1.2277 -1.5524 -0.6115 0.308 Uiso 1 1 calc R . .
C47 C -1.124(4) -1.499(2) -0.643(2) 0.35(2) Uani 1 1 d D . .
H47A H -1.0541 -1.4475 -0.6124 0.416 Uiso 1 1 calc R . .
H47B H -1.1780 -1.4513 -0.6677 0.416 Uiso 1 1 calc R . .
C48 C -1.0920(16) -1.5792(16) -0.7532(11) 0.156(7) Uani 1 1 d D . .
H48A H -1.0613 -1.5296 -0.7895 0.187 Uiso 1 1 calc R . .
H48B H -1.1599 -1.6249 -0.7963 0.187 Uiso 1 1 calc R . .
H48C H -1.0365 -1.6295 -0.7378 0.187 Uiso 1 1 calc R . .
C49 C -1.2799(9) -1.2862(10) -0.4932(9) 0.088(4) Uani 1 1 d . . .
H49A H -1.3204 -1.3456 -0.5543 0.105 Uiso 1 1 calc R . .
H49B H -1.2634 -1.2173 -0.5145 0.105 Uiso 1 1 calc R . .
C50 C -1.3559(11) -1.2594(12) -0.4147(10) 0.095(4) Uani 1 1 d . . .
H50A H -1.3834 -1.3313 -0.4031 0.114 Uiso 1 1 calc R . .
H50B H -1.3109 -1.2114 -0.3494 0.114 Uiso 1 1 calc R . .
C51 C -1.4576(9) -1.1982(11) -0.4436(9) 0.086(4) Uani 1 1 d . . .
H51A H -1.4299 -1.1273 -0.4569 0.104 Uiso 1 1 calc R . .
H51B H -1.5031 -1.2470 -0.5083 0.104 Uiso 1 1 calc R . .
C52 C -1.5318(12) -1.1690(14) -0.3677(13) 0.133(6) Uani 1 1 d . . .
H52A H -1.5908 -1.1266 -0.3919 0.159 Uiso 1 1 calc R . .
H52B H -1.4880 -1.1222 -0.3024 0.159 Uiso 1 1 calc R . .
H52C H -1.5659 -1.2388 -0.3584 0.159 Uiso 1 1 calc R . .
C62 C -0.3439(8) -0.2836(9) -0.1396(7) 0.057(2) Uani 1 1 d . . .
C63 C -0.2543(8) -0.1975(9) -0.0988(8) 0.060(2) Uani 1 1 d . . .
H63 H -0.2664 -0.1234 -0.0619 0.072 Uiso 1 1 calc R . .
C64 C -0.1454(7) -0.2240(9) -0.1141(8) 0.060(3) Uani 1 1 d . . .
C65 C -0.1367(9) -0.3316(10) -0.1767(8) 0.075(3) Uani 1 1 d . . .
H65 H -0.0664 -0.3503 -0.1942 0.090 Uiso 1 1 calc R . .
C66 C -0.2310(10) -0.4132(8) -0.2145(9) 0.074(3) Uani 1 1 d . . .
H66 H -0.2212 -0.4866 -0.2547 0.089 Uiso 1 1 calc R . .
C67 C -0.0476(9) -0.1371(9) -0.0726(9) 0.068(3) Uani 1 1 d . . .
H67 H 0.0130 -0.1439 -0.1088 0.082 Uiso 1 1 calc R . .
C68 C -0.0369(8) -0.0470(10) 0.0146(8) 0.069(3) Uani 1 1 d . . .
H68 H -0.0998 -0.0415 0.0478 0.083 Uiso 1 1 calc R . .
C69 C 0.0556(8) 0.0403(8) 0.0628(8) 0.059(2) Uani 1 1 d . . .
C70 C 0.0590(9) 0.1156(8) 0.1574(9) 0.070(3) Uani 1 1 d . . .
H70 H -0.0051 0.1144 0.1884 0.084 Uiso 1 1 calc R . .
C71 C 0.1522(11) 0.1947(9) 0.2112(9) 0.086(3) Uani 1 1 d . . .
H71 H 0.1501 0.2410 0.2779 0.103 Uiso 1 1 calc R . .
C72 C 0.2514(9) 0.2069(9) 0.1670(9) 0.069(3) Uani 1 1 d . . .
C73 C 0.2444(9) 0.1359(9) 0.0658(8) 0.075(3) Uani 1 1 d . . .
H73 H 0.3044 0.1427 0.0308 0.090 Uiso 1 1 calc R . .
C74 C 0.1512(9) 0.0555(9) 0.0157(8) 0.070(3) Uani 1 1 d . . .
H74 H 0.1513 0.0096 -0.0516 0.083 Uiso 1 1 calc R . .
C75 C 0.4378(11) 0.3024(10) 0.1758(10) 0.087(3) Uani 1 1 d . . .
H75A H 0.4798 0.3775 0.2125 0.105 Uiso 1 1 calc R . .
H75B H 0.4127 0.3010 0.1037 0.105 Uiso 1 1 calc R . .
C76 C 0.5180(12) 0.2054(11) 0.1804(11) 0.110(5) Uani 1 1 d . . .
H76A H 0.5500 0.2110 0.2522 0.132 Uiso 1 1 calc R . .
H76B H 0.4755 0.1296 0.1486 0.132 Uiso 1 1 calc R . .
C77 C 0.6102(14) 0.2221(16) 0.1228(13) 0.161(8) Uani 1 1 d . . .
H77A H 0.6556 0.2961 0.1566 0.193 Uiso 1 1 calc R . .
H77B H 0.5782 0.2202 0.0518 0.193 Uiso 1 1 calc R . .
C78 C 0.6932(13) 0.1094(14) 0.1237(13) 0.139(6) Uani 1 1 d . . .
H78A H 0.7549 0.1165 0.0872 0.167 Uiso 1 1 calc R . .
H78B H 0.6471 0.0369 0.0899 0.167 Uiso 1 1 calc R . .
H78C H 0.7237 0.1122 0.1944 0.167 Uiso 1 1 calc R . .
C79 C 0.3582(13) 0.3471(13) 0.3314(10) 0.111(4) Uani 1 1 d . . .
H79A H 0.4386 0.3605 0.3632 0.133 Uiso 1 1 calc R . .
H79B H 0.3181 0.3017 0.3668 0.133 Uiso 1 1 calc R . .
C80 C 0.3071(15) 0.4643(9) 0.3384(12) 0.142(6) Uani 1 1 d . . .
H80A H 0.3680 0.5145 0.3279 0.170 Uiso 1 1 calc R . .
H80B H 0.2491 0.4481 0.2759 0.170 Uiso 1 1 calc R . .
C81 C 0.269(2) 0.5208(14) 0.399(2) 0.259(15) Uani 1 1 d . . .
H81A H 0.3236 0.5323 0.4630 0.310 Uiso 1 1 calc R . .
H81B H 0.2033 0.4731 0.4055 0.310 Uiso 1 1 calc R . .
C82 C 0.2269(14) 0.6400(10) 0.4057(13) 0.132(5) Uani 1 1 d . . .
H82A H 0.2083 0.6721 0.4733 0.158 Uiso 1 1 calc R . .
H82B H 0.1602 0.6319 0.3531 0.158 Uiso 1 1 calc R . .
H82C H 0.2860 0.6906 0.3948 0.158 Uiso 1 1 calc R . .
C92 C -0.4621(9) -0.2601(8) -0.1226(8) 0.063(3) Uani 1 1 d . . .
C93 C -0.5539(9) -0.3448(9) -0.1648(8) 0.067(3) Uani 1 1 d . . .
H93 H -0.5409 -0.4165 -0.2061 0.081 Uiso 1 1 calc R . .
C94 C -0.6645(9) -0.3275(8) -0.1484(7) 0.063(3) Uani 1 1 d . . .
C95 C -0.6792(10) -0.2143(9) -0.0923(9) 0.072(3) Uani 1 1 d . . .
H95 H -0.7511 -0.1936 -0.0811 0.087 Uiso 1 1 calc R . .
C96 C -0.5840(11) -0.1356(11) -0.0548(9) 0.086(3) Uani 1 1 d . . .
H96 H -0.5950 -0.0613 -0.0175 0.103 Uiso 1 1 calc R . .
C97 C -0.7659(9) -0.4125(9) -0.1948(9) 0.070(3) Uani 1 1 d . . .
H97 H -0.8299 -0.4015 -0.1634 0.084 Uiso 1 1 calc R . .
C98 C -0.7735(9) -0.5020(8) -0.2765(9) 0.071(3) Uani 1 1 d . . .
H98 H -0.7085 -0.5120 -0.3066 0.085 Uiso 1 1 calc R . .
C99 C -0.8728(9) -0.5893(8) -0.3267(9) 0.066(3) Uani 1 1 d . . .
C100 C -0.9650(9) -0.6058(9) -0.2816(8) 0.066(3) Uani 1 1 d . . .
H100 H -0.9666 -0.5595 -0.2148 0.079 Uiso 1 1 calc R . .
C101 C -1.0548(7) -0.6883(9) -0.3317(8) 0.067(3) Uani 1 1 d . . .
H101 H -1.1149 -0.6985 -0.2977 0.081 Uiso 1 1 calc R . .
C102 C -1.0571(10) -0.7570(8) -0.4327(9) 0.072(3) Uani 1 1 d . . .
C103 C -0.9648(9) -0.7465(9) -0.4797(9) 0.078(3) Uani 1 1 d . . .
H103 H -0.9631 -0.7947 -0.5458 0.093 Uiso 1 1 calc R . .
C104 C -0.8750(11) -0.6640(11) -0.4281(10) 0.085(3) Uani 1 1 d . . .
H104 H -0.8131 -0.6567 -0.4608 0.102 Uiso 1 1 calc R . .
C105 C -1.1663(12) -0.8960(10) -0.5946(11) 0.101(4) Uani 1 1 d . . .
H105 H -1.2399 -0.8769 -0.6237 0.121 Uiso 1 1 calc R . .
H106 H -1.1101 -0.8552 -0.6204 0.121 Uiso 1 1 calc R . .
C106 C -1.1648(16) -1.0158(16) -0.6494(15) 0.076(5) Uiso 0.50 1 d P . .
H107 H -1.1827 -1.0289 -0.7243 0.091 Uiso 0.50 1 calc PR . .
H108 H -1.2178 -1.0657 -0.6288 0.091 Uiso 0.50 1 calc PR . .
C107 C -1.0503(14) -1.0327(14) -0.6165(13) 0.066(4) Uiso 0.50 1 d PD . .
H109 H -1.0331 -1.0245 -0.5423 0.079 Uiso 0.50 1 calc PR . .
H110 H -0.9967 -0.9807 -0.6342 0.079 Uiso 0.50 1 calc PR . .
C108 C -1.0523(16) -1.1623(16) -0.6836(15) 0.222(13) Uani 1 1 d D . .
H111 H -0.9786 -1.1884 -0.6688 0.266 Uiso 1 1 calc R . .
H112 H -1.0705 -1.1670 -0.7564 0.266 Uiso 1 1 calc R . .
H113 H -1.1090 -1.2103 -0.6665 0.266 Uiso 1 1 calc R . .
C109 C -1.2527(10) -0.8513(10) -0.4328(11) 0.095(4) Uani 1 1 d . . .
H114 H -1.2253 -0.8427 -0.3595 0.114 Uiso 1 1 calc R . .
H115 H -1.2911 -0.9291 -0.4641 0.114 Uiso 1 1 calc R . .
C110 C -1.3383(10) -0.7630(13) -0.4433(11) 0.129(6) Uani 1 1 d . . .
H116 H -1.2939 -0.6883 -0.4278 0.155 Uiso 1 1 calc R . .
H117 H -1.3738 -0.7832 -0.5163 0.155 Uiso 1 1 calc R . .
C111 C -1.4183(14) -0.7474(17) -0.3916(13) 0.176(9) Uani 1 1 d . . .
H118 H -1.3797 -0.7304 -0.3197 0.211 Uiso 1 1 calc R . .
H119 H -1.4593 -0.8240 -0.4079 0.211 Uiso 1 1 calc R . .
C112 C -1.5004(13) -0.6766(13) -0.3878(11) 0.126(5) Uani 1 1 d . . .
H120 H -1.5516 -0.6944 -0.3447 0.151 Uiso 1 1 calc R . .
H121 H -1.5421 -0.6868 -0.4569 0.151 Uiso 1 1 calc R . .
H122 H -1.4667 -0.5978 -0.3589 0.151 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.091(6) 0.040(4) 0.073(6) 0.018(4) 0.010(5) 0.012(4)
N2 0.066(6) 0.080(7) 0.091(7) 0.012(5) 0.018(5) -0.007(5)
N3 0.062(5) 0.078(6) 0.095(7) 0.033(5) 0.008(5) 0.005(5)
N4 0.064(6) 0.069(6) 0.081(6) 0.009(5) -0.001(5) 0.008(5)
N51 0.067(6) 0.077(6) 0.081(6) 0.019(5) 0.008(5) 0.010(5)
N52 0.066(6) 0.081(7) 0.087(7) 0.012(5) 0.003(5) -0.006(5)
N53 0.073(6) 0.049(5) 0.073(6) -0.001(4) 0.025(5) 0.006(4)
N54 0.091(7) 0.078(6) 0.090(7) 0.030(6) 0.020(6) 0.010(5)
C2 0.059(6) 0.081(7) 0.054(6) 0.024(5) 0.007(4) 0.011(5)
C3 0.074(7) 0.050(5) 0.059(6) 0.001(4) 0.017(5) 0.000(5)
C4 0.078(7) 0.069(7) 0.047(5) 0.009(5) 0.023(5) 0.002(5)
C5 0.065(6) 0.083(7) 0.065(6) 0.013(6) 0.001(5) 0.012(6)
C6 0.087(8) 0.064(6) 0.073(7) 0.013(5) 0.018(6) 0.036(6)
C7 0.070(7) 0.069(7) 0.056(6) -0.001(5) 0.008(5) -0.002(5)
C8 0.070(7) 0.094(8) 0.060(6) 0.031(6) 0.014(5) -0.004(6)
C9 0.053(6) 0.088(8) 0.058(6) 0.026(5) 0.014(5) -0.007(5)
C10 0.090(8) 0.061(6) 0.071(7) 0.018(5) 0.024(6) 0.003(6)
C11 0.099(9) 0.106(10) 0.065(7) 0.021(7) 0.010(6) 0.030(8)
C12 0.070(7) 0.057(6) 0.070(7) 0.005(5) 0.025(6) 0.007(5)
C13 0.062(6) 0.066(6) 0.072(6) 0.019(5) 0.014(5) 0.005(5)
C14 0.055(6) 0.063(6) 0.090(8) 0.016(6) 0.007(5) 0.007(5)
C15 0.085(7) 0.098(8) 0.056(6) 0.024(6) -0.004(5) 0.020(6)
C16 0.059(6) 0.068(6) 0.077(7) 0.012(5) 0.018(5) -0.004(5)
C17 0.112(10) 0.114(10) 0.153(13) 0.074(9) 0.037(10) 0.048(8)
C18 0.142(12) 0.139(13) 0.084(9) 0.034(8) 0.043(9) 0.034(10)
C19 0.106(9) 0.071(7) 0.123(10) 0.040(7) 0.021(8) 0.007(6)
C20 0.41(4) 0.178(18) 0.074(9) -0.046(10) 0.013(15) 0.10(2)
C21 0.46(4) 0.49(5) 0.086(12) -0.002(18) 0.138(19) 0.22(4)
C22 0.142(13) 0.122(12) 0.22(2) 0.006(12) 0.031(13) 0.038(10)
C32 0.086(8) 0.035(5) 0.064(6) 0.011(4) 0.013(5) -0.002(4)
C33 0.076(7) 0.073(7) 0.073(7) 0.026(5) 0.008(6) 0.010(6)
C34 0.062(6) 0.066(7) 0.074(7) 0.031(5) 0.004(5) 0.000(5)
C35 0.088(8) 0.064(7) 0.092(8) 0.035(6) 0.026(6) 0.020(6)
C36 0.094(9) 0.057(6) 0.107(9) 0.039(6) -0.001(7) -0.009(6)
C37 0.072(7) 0.082(8) 0.108(9) 0.050(7) 0.031(7) 0.034(6)
C38 0.071(7) 0.058(6) 0.080(7) 0.010(5) 0.023(6) 0.029(5)
C39 0.070(7) 0.067(7) 0.068(7) 0.014(5) 0.015(6) 0.026(5)
C40 0.076(7) 0.087(8) 0.074(7) 0.031(6) 0.019(6) 0.019(6)
C41 0.065(7) 0.064(7) 0.098(9) 0.015(6) 0.017(6) 0.008(5)
C42 0.058(6) 0.079(7) 0.060(6) 0.022(5) -0.001(5) 0.001(5)
C43 0.037(5) 0.055(6) 0.120(9) 0.017(6) 0.015(5) -0.001(4)
C44 0.079(7) 0.060(7) 0.084(8) 0.012(5) 0.014(6) 0.015(6)
C45 0.077(7) 0.075(8) 0.097(8) -0.010(6) 0.003(6) -0.010(6)
C46 0.44(4) 0.170(19) 0.24(3) 0.074(17) 0.22(3) 0.13(2)
C47 0.60(6) 0.29(3) 0.25(3) 0.15(3) 0.26(4) 0.03(3)
C48 0.197(17) 0.194(17) 0.099(9) 0.046(10) 0.073(10) 0.053(13)
C49 0.064(7) 0.091(8) 0.097(9) 0.008(6) 0.023(6) -0.021(6)
C50 0.087(9) 0.113(10) 0.082(9) 0.028(7) 0.004(7) 0.006(7)
C51 0.055(6) 0.125(10) 0.077(7) 0.031(7) 0.005(5) 0.008(6)
C52 0.084(9) 0.155(15) 0.158(14) 0.036(11) 0.018(9) 0.060(9)
C62 0.055(6) 0.066(6) 0.053(5) 0.012(4) 0.021(4) 0.011(4)
C63 0.058(6) 0.063(6) 0.062(6) 0.028(4) 0.006(5) 0.003(4)
C64 0.049(5) 0.066(6) 0.068(7) 0.018(5) 0.016(5) 0.013(5)
C65 0.055(6) 0.094(8) 0.081(8) 0.029(6) 0.014(5) 0.022(6)
C66 0.068(7) 0.044(5) 0.098(9) -0.001(5) 0.018(6) 0.005(5)
C67 0.053(6) 0.070(7) 0.075(7) 0.013(6) 0.009(5) 0.006(5)
C68 0.049(5) 0.097(8) 0.072(7) 0.037(6) 0.011(5) 0.025(5)
C69 0.044(5) 0.065(6) 0.065(6) 0.022(5) 0.001(4) 0.004(4)
C70 0.065(6) 0.057(6) 0.080(7) -0.001(5) 0.025(5) -0.004(5)
C71 0.125(10) 0.067(7) 0.076(7) 0.023(6) 0.040(7) 0.021(7)
C72 0.061(6) 0.073(7) 0.078(7) 0.029(6) 0.010(6) 0.013(5)
C73 0.082(7) 0.076(7) 0.064(7) 0.019(5) 0.003(6) 0.022(6)
C74 0.065(6) 0.074(7) 0.062(6) 0.004(5) 0.017(5) 0.011(5)
C75 0.093(8) 0.076(7) 0.087(7) 0.018(6) 0.015(6) -0.005(6)
C76 0.117(10) 0.112(9) 0.113(10) 0.063(8) 0.016(8) -0.027(8)
C77 0.140(13) 0.224(18) 0.123(12) 0.077(12) 0.011(10) -0.051(13)
C78 0.107(10) 0.142(13) 0.156(15) 0.021(11) 0.007(10) 0.064(10)
C79 0.113(10) 0.124(11) 0.073(8) 0.002(8) 0.002(8) -0.004(9)
C80 0.222(16) 0.054(6) 0.167(13) 0.008(7) 0.129(12) 0.012(8)
C81 0.42(3) 0.123(12) 0.38(3) 0.152(17) 0.33(3) 0.150(17)
C82 0.166(13) 0.082(7) 0.178(14) 0.055(8) 0.076(11) 0.049(8)
C92 0.062(6) 0.054(6) 0.068(6) 0.020(5) -0.006(5) -0.006(5)
C93 0.067(7) 0.066(6) 0.064(6) 0.000(5) 0.024(5) 0.014(5)
C94 0.073(7) 0.058(6) 0.059(6) 0.025(5) 0.004(5) 0.002(5)
C95 0.072(7) 0.060(6) 0.077(7) 0.006(5) 0.015(6) 0.007(5)
C96 0.086(8) 0.097(9) 0.071(7) 0.013(6) 0.015(6) 0.024(7)
C97 0.062(6) 0.072(7) 0.081(8) 0.027(6) 0.021(6) 0.008(5)
C98 0.076(7) 0.055(6) 0.080(7) 0.018(5) 0.017(6) -0.012(5)
C99 0.071(6) 0.061(6) 0.079(7) 0.033(5) 0.025(6) 0.018(5)
C100 0.067(6) 0.074(7) 0.062(6) 0.028(5) 0.008(5) 0.008(5)
C101 0.041(5) 0.073(7) 0.092(8) 0.025(6) 0.026(5) -0.003(4)
C102 0.084(8) 0.049(6) 0.077(7) 0.012(5) 0.007(6) -0.007(5)
C103 0.066(7) 0.071(7) 0.080(7) -0.001(6) 0.015(6) -0.017(5)
C104 0.081(8) 0.096(9) 0.085(8) 0.033(7) 0.027(7) 0.002(6)
C105 0.109(10) 0.069(8) 0.108(10) 0.008(7) 0.011(9) -0.019(7)
C108 0.173(17) 0.28(3) 0.168(16) -0.021(17) 0.098(14) -0.099(18)
C109 0.065(7) 0.076(7) 0.125(10) 0.007(7) 0.010(7) -0.009(6)
C110 0.072(7) 0.167(13) 0.124(11) -0.003(9) 0.004(7) 0.061(8)
C111 0.185(14) 0.27(2) 0.149(14) 0.123(14) 0.093(12) 0.187(15)
C112 0.139(13) 0.138(12) 0.091(9) 0.025(8) 0.004(9) 0.029(10)
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
N1 C6 1.295(14) . ?
N1 C2 1.366(13) . ?
N2 C12 1.376(12) . ?
N2 C19 1.459(14) . ?
N2 C15 1.468(14) . ?
N3 C32 1.311(12) . ?
N3 C36 1.383(15) . ?
N4 C42 1.390(12) . ?
N4 C45 1.426(14) . ?
N4 C49 1.482(14) . ?
N51 C66 1.315(14) . ?
N51 C62 1.349(12) . ?
N52 C75 1.381(15) . ?
N52 C72 1.380(12) . ?
N52 C79 1.461(15) . ?
N53 C92 1.324(12) . ?
N53 C96 1.353(14) . ?
N54 C102 1.379(13) . ?
N54 C105 1.438(15) . ?
N54 C109 1.531(16) . ?
C2 C3 1.406(13) . ?
C2 C32 1.488(8) . ?
C3 C4 1.384(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.414(14) . ?
C4 C7 1.461(14) . ?
C5 C6 1.355(14) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.312(14) . ?
C7 H7 0.9300 . ?
C8 C9 1.478(14) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(16) . ?
C9 C14 1.393(14) . ?
C10 C11 1.404(15) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(15) . ?
C11 H11 0.9300 . ?
C12 C13 1.431(14) . ?
C13 C14 1.385(13) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.534(15) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.520(16) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.537(18) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.575(16) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 0.833(19) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.38(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C32 C33 1.369(14) . ?
C33 C34 1.407(15) . ?
C33 H33 0.9300 . ?
C34 C35 1.389(14) . ?
C34 C37 1.472(15) . ?
C35 C36 1.382(15) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 C38 1.306(14) . ?
C37 H37 0.9300 . ?
C38 C39 1.454(15) . ?
C38 H38 0.9300 . ?
C39 C40 1.393(15) . ?
C39 C44 1.416(15) . ?
C40 C41 1.350(14) . ?
C40 H40 0.9300 . ?
C41 C42 1.358(14) . ?
C41 H41 0.9300 . ?
C42 C43 1.415(13) . ?
C43 C44 1.369(13) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?
C45 C46 1.42(2) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 C47 1.01(3) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C47 C48 1.652(18) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 C50 1.486(17) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 C51 1.509(17) . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C51 C52 1.446(17) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C62 C63 1.376(12) . ?
C62 C92 1.494(8) . ?
C63 C64 1.388(13) . ?
C63 H63 0.9300 . ?
C64 C65 1.365(14) . ?
C64 C67 1.449(13) . ?
C65 C66 1.380(14) . ?
C65 H65 0.9300 . ?
C66 H66 0.9300 . ?
C67 C68 1.354(14) . ?
C67 H67 0.9300 . ?
C68 C69 1.418(13) . ?
C68 H68 0.9300 . ?
C69 C70 1.349(14) . ?
C69 C74 1.417(14) . ?
C70 C71 1.383(15) . ?
C70 H70 0.9300 . ?
C71 C72 1.424(15) . ?
C71 H71 0.9300 . ?
C72 C73 1.393(14) . ?
C73 C74 1.382(14) . ?
C73 H73 0.9300 . ?
C74 H74 0.9300 . ?
C75 C76 1.560(19) . ?
C75 H75A 0.9700 . ?
C75 H75B 0.9700 . ?
C76 C77 1.478(19) . ?
C76 H76A 0.9700 . ?
C76 H76B 0.9700 . ?
C77 C78 1.73(2) . ?
C77 H77A 0.9700 . ?
C77 H77B 0.9700 . ?
C78 H78A 0.9600 . ?
C78 H78B 0.9600 . ?
C78 H78C 0.9600 . ?
C79 C80 1.556(19) . ?
C79 H79A 0.9700 . ?
C79 H79B 0.9700 . ?
C80 C81 1.096(17) . ?
C80 H80A 0.9700 . ?
C80 H80B 0.9700 . ?
C81 C82 1.533(17) . ?
C81 H81A 0.9700 . ?
C81 H81B 0.9700 . ?
C82 H82A 0.9600 . ?
C82 H82B 0.9600 . ?
C82 H82C 0.9600 . ?
C92 C93 1.385(13) . ?
C93 C94 1.389(14) . ?
C93 H93 0.9300 . ?
C94 C95 1.408(14) . ?
C94 C97 1.472(14) . ?
C95 C96 1.368(15) . ?
C95 H95 0.9300 . ?
C96 H96 0.9300 . ?
C97 C98 1.307(14) . ?
C97 H97 0.9300 . ?
C98 C99 1.477(14) . ?
C98 H98 0.9300 . ?
C99 C100 1.368(14) . ?
C99 C104 1.419(16) . ?
C100 C101 1.369(13) . ?
C100 H100 0.9300 . ?
C101 C102 1.391(14) . ?
C101 H101 0.9300 . ?
C102 C103 1.371(15) . ?
C103 C104 1.373(15) . ?
C103 H103 0.9300 . ?
C104 H104 0.9300 . ?
C105 C106 1.44(2) . ?
C105 H105 0.9700 . ?
C105 H106 0.9700 . ?
C106 C107 1.41(2) . ?
C106 H107 0.9700 . ?
C106 H108 0.9700 . ?
C107 C108 1.577(16) . ?
C107 H109 0.9700 . ?
C107 H110 0.9700 . ?
C108 H111 0.9600 . ?
C108 H112 0.9600 . ?
C108 H113 0.9600 . ?
C109 C110 1.536(17) . ?
C109 H114 0.9700 . ?
C109 H115 0.9700 . ?
C110 C111 1.263(19) . ?
C110 H116 0.9700 . ?
C110 H117 0.9700 . ?
C111 C112 1.334(17) . ?
C111 H118 0.9700 . ?
C111 H119 0.9700 . ?
C112 H120 0.9600 . ?
C112 H121 0.9600 . ?
C112 H122 0.9600 . ?