#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/11/4021129.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_4021129
loop_
_publ_author_name
'Monika Mazik'
'Wolfgang Radunz'
'Roland Boese'
_publ_section_title
;
 Molecular Recognition of Carbohydrates with Acyclic Pyridine-Based Receptors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7448
_journal_page_last               7462
_journal_paper_doi               10.1021/jo048979k
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C30 H30 N6 O3'
_chemical_formula_weight         522.60
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                104.882(2)
_cell_angle_beta                 93.929(2)
_cell_angle_gamma                119.408(2)
_cell_formula_units_Z            4
_cell_length_a                   14.4095(17)
_cell_length_b                   14.4662(17)
_cell_length_c                   15.2004(18)
_cell_measurement_temperature    203(2)
_cell_volume                     2595.4(5)
_diffrn_ambient_temperature      203(2)
_exptl_crystal_density_diffrn    1.337
_cod_database_code               4021129
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_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 0.16410(9) 0.47972(10) 0.42708(10) 0.0433(3) Uani 1 1 d . . .
O2 O -0.33013(9) 0.35044(10) 0.30847(9) 0.0395(3) Uani 1 1 d . . .
O3 O 0.05134(11) 0.82228(12) 0.33602(14) 0.0668(5) Uani 1 1 d . . .
N1 N -0.00091(11) 0.31440(12) 0.37487(11) 0.0360(3) Uani 1 1 d . . .
H1 H -0.0754 0.2738 0.3435 0.043 Uiso 1 1 d R . .
N2 N -0.06076(12) 0.13355(12) 0.36737(11) 0.0398(4) Uani 1 1 d . . .
N3 N -0.30381(11) 0.52463(12) 0.37368(10) 0.0353(3) Uani 1 1 d . . .
H3 H -0.2518 0.5895 0.4003 0.042 Uiso 1 1 d R . .
N4 N -0.41092(12) 0.59742(13) 0.40619(11) 0.0400(4) Uani 1 1 d . . .
N5 N 0.20607(11) 0.81947(12) 0.36154(11) 0.0396(4) Uani 1 1 d . . .
H5 H 0.2330 0.7800 0.3696 0.048 Uiso 1 1 d R . .
N6 N 0.38669(11) 0.94202(12) 0.37315(10) 0.0355(3) Uani 1 1 d . . .
C1 C 0.00930(13) 0.48798(13) 0.37821(11) 0.0291(3) Uani 1 1 d . . .
C2 C -0.10237(13) 0.44308(14) 0.36687(12) 0.0305(4) Uani 1 1 d . . .
H2 H -0.1494 0.3673 0.3658 0.037 Uiso 1 1 d R . .
C3 C -0.14694(13) 0.50748(13) 0.35664(11) 0.0293(4) Uani 1 1 d . . .
C4 C -0.07895(13) 0.61586(14) 0.35582(12) 0.0324(4) Uani 1 1 d . . .
H4 H -0.1093 0.6605 0.3494 0.039 Uiso 1 1 d R . .
C5 C 0.03303(13) 0.66076(13) 0.36366(12) 0.0313(4) Uani 1 1 d . . .
C6 C 0.07692(13) 0.59691(14) 0.37628(12) 0.0315(4) Uani 1 1 d . . .
H6 H 0.1542 0.6279 0.3836 0.038 Uiso 1 1 d R . .
C7 C 0.06523(13) 0.42722(14) 0.39516(12) 0.0300(4) Uani 1 1 d . . .
C8 C 0.02689(13) 0.23706(14) 0.38880(12) 0.0322(4) Uani 1 1 d . . .
C9 C 0.13355(15) 0.26575(16) 0.41982(13) 0.0385(4) Uani 1 1 d . . .
H9 H 0.1945 0.3410 0.4333 0.046 Uiso 1 1 d R . .
C10 C 0.14760(16) 0.18055(17) 0.42938(15) 0.0479(5) Uani 1 1 d . . .
H10 H 0.2195 0.1964 0.4518 0.057 Uiso 1 1 d R . .
C11 C 0.05880(17) 0.07299(17) 0.40728(15) 0.0498(5) Uani 1 1 d . . .
H11 H 0.0679 0.0136 0.4143 0.060 Uiso 1 1 d R . .
C12 C -0.04503(16) 0.05149(16) 0.37588(14) 0.0427(4) Uani 1 1 d . . .
C13 C -0.14452(18) -0.06596(17) 0.34722(17) 0.0580(6) Uani 1 1 d . . .
H13A H -0.1256 -0.1126 0.3689 0.070 Uiso 1 1 d R . .
H13B H -0.1652 -0.0960 0.2802 0.070 Uiso 1 1 d R . .
C14 C -0.2400(2) -0.0722(2) 0.3830(3) 0.0927(10) Uani 1 1 d . . .
H14A H -0.2168 -0.0295 0.4493 0.139 Uiso 1 1 d R . .
H14B H -0.2946 -0.1502 0.3733 0.139 Uiso 1 1 d R . .
H14C H -0.2711 -0.0413 0.3497 0.139 Uiso 1 1 d R . .
C15 C -0.26904(13) 0.45268(14) 0.34388(12) 0.0317(4) Uani 1 1 d . . .
C16 C -0.41108(13) 0.50247(15) 0.37183(12) 0.0327(4) Uani 1 1 d . . .
C17 C -0.50411(14) 0.39601(15) 0.33835(13) 0.0379(4) Uani 1 1 d . . .
H17 H -0.5000 0.3302 0.3151 0.045 Uiso 1 1 d R . .
C18 C -0.60368(15) 0.38862(17) 0.33968(15) 0.0460(5) Uani 1 1 d . . .
H18 H -0.6705 0.3163 0.3168 0.055 Uiso 1 1 d R . .
C19 C -0.60617(15) 0.48506(17) 0.37416(15) 0.0458(5) Uani 1 1 d . . .
H19 H -0.6745 0.4813 0.3748 0.055 Uiso 1 1 d R . .
C20 C -0.50861(15) 0.58772(16) 0.40773(14) 0.0425(5) Uani 1 1 d . . .
C21 C -0.50605(19) 0.69543(19) 0.44969(18) 0.0635(7) Uani 1 1 d . . .
H21A H -0.4311 0.7565 0.4721 0.076 Uiso 1 1 d R . .
H21B H -0.5388 0.6903 0.5025 0.076 Uiso 1 1 d R . .
C22 C -0.5627(3) 0.7213(2) 0.3862(2) 0.0979(11) Uani 1 1 d . . .
H22A H -0.5316 0.7243 0.3316 0.147 Uiso 1 1 d R . .
H22B H -0.5543 0.7934 0.4172 0.147 Uiso 1 1 d R . .
H22C H -0.6398 0.6630 0.3671 0.147 Uiso 1 1 d R . .
C23 C 0.09725(14) 0.77484(15) 0.35322(14) 0.0376(4) Uani 1 1 d . . .
C24 C 0.28545(13) 0.92138(14) 0.35121(12) 0.0331(4) Uani 1 1 d . . .
C25 C 0.26136(15) 0.99120(15) 0.31999(13) 0.0382(4) Uani 1 1 d . . .
H25 H 0.1876 0.9737 0.3041 0.046 Uiso 1 1 d R . .
C26 C 0.34950(15) 1.08710(15) 0.31269(14) 0.0416(4) Uani 1 1 d . . .
H26 H 0.3371 1.1375 0.2906 0.050 Uiso 1 1 d R . .
C27 C 0.45503(14) 1.11073(15) 0.33615(13) 0.0367(4) Uani 1 1 d . . .
H27 H 0.5158 1.1777 0.3315 0.044 Uiso 1 1 d R . .
C28 C 0.47142(14) 1.03608(14) 0.36671(12) 0.0333(4) Uani 1 1 d . . .
C29 C 0.58224(14) 1.05187(16) 0.39394(14) 0.0416(4) Uani 1 1 d . . .
H29A H 0.5848 0.9934 0.3491 0.050 Uiso 1 1 d R . .
H29B H 0.5884 1.0415 0.4535 0.050 Uiso 1 1 d R . .
C30 C 0.68133(15) 1.16401(18) 0.40131(15) 0.0499(5) Uani 1 1 d . . .
H30A H 0.6770 1.1754 0.3414 0.075 Uiso 1 1 d R . .
H30B H 0.7479 1.1646 0.4179 0.075 Uiso 1 1 d R . .
H30C H 0.6821 1.2239 0.4487 0.075 Uiso 1 1 d R . .
O4 O 0.43606(12) -0.29945(12) 0.13844(14) 0.0687(5) Uani 1 1 d . . .
O5 O 0.34024(9) 0.05491(10) 0.06295(9) 0.0420(3) Uani 1 1 d . . .
O6 O 0.83253(9) 0.18347(10) 0.18840(9) 0.0406(3) Uani 1 1 d . . .
N7 N 0.29429(11) -0.27378(12) 0.15010(11) 0.0366(3) Uani 1 1 d . . .
H7 H 0.2778 -0.2251 0.1528 0.044 Uiso 1 1 d R . .
N8 N 0.11121(11) -0.39262(12) 0.13402(10) 0.0354(3) Uani 1 1 d . . .
N9 N 0.50244(11) 0.22213(12) 0.12147(11) 0.0349(3) Uani 1 1 d . . .
H9A H 0.5739 0.2579 0.1538 0.042 Uiso 1 1 d R . .
N10 N 0.55527(12) 0.40406(12) 0.13713(11) 0.0366(3) Uani 1 1 d . . .
N11 N 0.80315(11) 0.00652(12) 0.13511(11) 0.0362(3) Uani 1 1 d . . .
H11A H 0.7547 -0.0596 0.1082 0.043 Uiso 1 1 d R . .
N12 N 0.90851(11) -0.06993(12) 0.11093(11) 0.0365(3) Uani 1 1 d . . .
C31 C 0.46607(13) -0.12444(14) 0.13587(12) 0.0317(4) Uani 1 1 d . . .
C32 C 0.42415(13) -0.06028(14) 0.11932(12) 0.0313(4) Uani 1 1 d . . .
H32 H 0.3465 -0.0919 0.1078 0.038 Uiso 1 1 d R . .
C33 C 0.49343(13) 0.04859(13) 0.11865(11) 0.0286(3) Uani 1 1 d . . .
C34 C 0.60581(13) 0.09349(14) 0.13337(11) 0.0295(4) Uani 1 1 d . . .
H34 H 0.6539 0.1692 0.1347 0.035 Uiso 1 1 d R . .
C35 C 0.64868(13) 0.02863(14) 0.14693(12) 0.0303(4) Uani 1 1 d . . .
C36 C 0.57889(13) -0.07943(14) 0.14803(12) 0.0328(4) Uani 1 1 d . . .
H36 H 0.6080 -0.1241 0.1575 0.039 Uiso 1 1 d R . .
C37 C 0.39810(14) -0.24050(15) 0.14142(14) 0.0373(4) Uani 1 1 d . . .
C38 C 0.20997(14) -0.37983(14) 0.14899(12) 0.0339(4) Uani 1 1 d . . .
C39 C 0.22730(15) -0.46207(16) 0.16270(15) 0.0442(5) Uani 1 1 d . . .
H39 H 0.2994 -0.4499 0.1734 0.053 Uiso 1 1 d R . .
C40 C 0.13620(16) -0.56130(16) 0.16012(16) 0.0491(5) Uani 1 1 d . . .
H40 H 0.1443 -0.6202 0.1698 0.059 Uiso 1 1 d R . .
C41 C 0.03262(15) -0.57698(16) 0.14364(14) 0.0434(5) Uani 1 1 d . . .
H41 H -0.0311 -0.6462 0.1412 0.052 Uiso 1 1 d R . .
C42 C 0.02262(14) -0.49068(15) 0.13007(12) 0.0352(4) Uani 1 1 d . . .
C43 C -0.08495(14) -0.49797(16) 0.10999(13) 0.0414(4) Uani 1 1 d . . .
H43A H -0.0910 -0.4827 0.0528 0.050 Uiso 1 1 d R . .
H43B H -0.0836 -0.4398 0.1588 0.050 Uiso 1 1 d R . .
C44 C -0.18699(15) -0.61010(18) 0.09986(15) 0.0499(5) Uani 1 1 d . . .
H44A H -0.1903 -0.6697 0.0499 0.075 Uiso 1 1 d R . .
H44B H -0.2516 -0.6067 0.0856 0.075 Uiso 1 1 d R . .
H44C H -0.1838 -0.6252 0.1582 0.075 Uiso 1 1 d R . .
C45 C 0.43826(13) 0.10888(14) 0.09855(11) 0.0297(4) Uani 1 1 d . . .
C46 C 0.47092(14) 0.29683(15) 0.10745(12) 0.0331(4) Uani 1 1 d . . .
C47 C 0.36432(15) 0.26326(17) 0.06873(14) 0.0406(4) Uani 1 1 d . . .
H47 H 0.3058 0.1858 0.0493 0.049 Uiso 1 1 d R . .
C48 C 0.34652(16) 0.34657(18) 0.06032(15) 0.0479(5) Uani 1 1 d . . .
H48 H 0.2747 0.3276 0.0331 0.057 Uiso 1 1 d R . .
C49 C 0.43193(16) 0.45708(18) 0.09031(15) 0.0480(5) Uani 1 1 d . . .
H49 H 0.4204 0.5153 0.0840 0.058 Uiso 1 1 d R . .
C50 C 0.53584(15) 0.48355(15) 0.12959(13) 0.0390(4) Uani 1 1 d . . .
C51 C 0.63013(17) 0.60370(16) 0.16735(16) 0.0499(5) Uani 1 1 d . . .
H51A H 0.6329 0.6338 0.2322 0.060 Uiso 1 1 d R . .
H51B H 0.6164 0.6463 0.1351 0.060 Uiso 1 1 d R . .
C52 C 0.74025(17) 0.61880(18) 0.15792(17) 0.0574(6) Uani 1 1 d . . .
H52A H 0.7560 0.5780 0.1920 0.086 Uiso 1 1 d R . .
H52B H 0.7966 0.6981 0.1834 0.086 Uiso 1 1 d R . .
H52C H 0.7387 0.5899 0.0925 0.086 Uiso 1 1 d R . .
C53 C 0.77009(13) 0.08091(14) 0.15899(12) 0.0320(4) Uani 1 1 d . . .
C54 C 0.90934(13) 0.02605(14) 0.13508(12) 0.0323(4) Uani 1 1 d . . .
C55 C 1.00248(14) 0.13180(15) 0.15640(13) 0.0369(4) Uani 1 1 d . . .
H55 H 1.0000 0.1990 0.1744 0.044 Uiso 1 1 d R . .
C56 C 1.09997(14) 0.13605(16) 0.15066(14) 0.0423(4) Uani 1 1 d . . .
H56 H 1.1665 0.2074 0.1640 0.051 Uiso 1 1 d R . .
C57 C 1.10198(14) 0.03830(16) 0.12558(14) 0.0409(4) Uani 1 1 d . . .
H57 H 1.1692 0.0408 0.1209 0.049 Uiso 1 1 d R . .
C58 C 1.00445(14) -0.06386(15) 0.10704(13) 0.0363(4) Uani 1 1 d . . .
C59 C 0.99744(16) -0.17559(17) 0.08259(17) 0.0513(5) Uani 1 1 d . . .
H59A H 0.9404 -0.2272 0.0273 0.062 Uiso 1 1 d R . .
H59B H 0.9765 -0.2049 0.1326 0.062 Uiso 1 1 d R . .
C60 C 1.10007(16) -0.17382(17) 0.06687(15) 0.0482(5) Uani 1 1 d . . .
H60A H 1.1233 -0.1426 0.0175 0.072 Uiso 1 1 d R . .
H60B H 1.0868 -0.2494 0.0489 0.072 Uiso 1 1 d R . .
H60C H 1.1569 -0.1270 0.1240 0.072 Uiso 1 1 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
O1 C7 1.2228(19) . ?
O2 C15 1.225(2) . ?
O3 C23 1.221(2) . ?
N1 C7 1.357(2) . ?
N1 C8 1.417(2) . ?
N2 C8 1.334(2) . ?
N2 C12 1.348(2) . ?
N3 C15 1.357(2) . ?
N3 C16 1.413(2) . ?
N4 C16 1.337(2) . ?
N4 C20 1.347(2) . ?
N5 C23 1.352(2) . ?
N5 C24 1.412(2) . ?
N6 C24 1.335(2) . ?
N6 C28 1.343(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.398(2) . ?
C1 C7 1.507(2) . ?
C2 C3 1.397(2) . ?
C3 C4 1.386(2) . ?
C3 C15 1.505(2) . ?
C4 C5 1.394(2) . ?
C5 C6 1.392(2) . ?
C5 C23 1.503(2) . ?
C8 C9 1.389(2) . ?
C9 C10 1.384(3) . ?
C10 C11 1.374(3) . ?
C11 C12 1.390(3) . ?
C12 C13 1.508(3) . ?
C13 C14 1.484(3) . ?
C16 C17 1.380(2) . ?
C17 C18 1.387(2) . ?
C18 C19 1.378(3) . ?
C19 C20 1.380(3) . ?
C20 C21 1.505(3) . ?
C21 C22 1.453(3) . ?
C24 C25 1.391(2) . ?
C25 C26 1.385(3) . ?
C26 C27 1.382(2) . ?
C27 C28 1.390(2) . ?
C28 C29 1.509(2) . ?
C29 C30 1.514(3) . ?
O4 C37 1.213(2) . ?
O5 C45 1.2217(19) . ?
O6 C53 1.226(2) . ?
N7 C37 1.356(2) . ?
N7 C38 1.408(2) . ?
N8 C38 1.337(2) . ?
N8 C42 1.346(2) . ?
N9 C45 1.355(2) . ?
N9 C46 1.417(2) . ?
N10 C50 1.339(2) . ?
N10 C46 1.342(2) . ?
N11 C53 1.358(2) . ?
N11 C54 1.413(2) . ?
N12 C54 1.336(2) . ?
N12 C58 1.348(2) . ?
C31 C32 1.393(2) . ?
C31 C36 1.399(2) . ?
C31 C37 1.501(2) . ?
C32 C33 1.394(2) . ?
C33 C34 1.392(2) . ?
C33 C45 1.507(2) . ?
C34 C35 1.398(2) . ?
C35 C36 1.388(2) . ?
C35 C53 1.501(2) . ?
C38 C39 1.390(2) . ?
C39 C40 1.378(3) . ?
C40 C41 1.389(3) . ?
C41 C42 1.388(3) . ?
C42 C43 1.505(2) . ?
C43 C44 1.522(3) . ?
C46 C47 1.392(2) . ?
C47 C48 1.383(3) . ?
C48 C49 1.377(3) . ?
C49 C50 1.394(3) . ?
C50 C51 1.503(3) . ?
C51 C52 1.514(3) . ?
C54 C55 1.384(2) . ?
C55 C56 1.385(2) . ?
C56 C57 1.382(3) . ?
C57 C58 1.389(2) . ?
C58 C59 1.512(3) . ?
C59 C60 1.503(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9504839
