#------------------------------------------------------------------------------ #$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: svn://www.crystallography.net/cod/cif/2/2006192.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_2006192 _journal_name_full 'Acta Crystallographica Section C' _journal_year 1997 _journal_volume 53 _journal_page_first 716 _journal_page_last 718 _publ_section_title ; 6-L-Alanineferrirubin, a Ferrichrome-type Siderophore from the Fungus Aspergillus ochraceous ; _space_group_IT_number 4 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _[local]_cod_cif_authors_sg_H-M 'P 21' loop_ _publ_author_name 'Hossain, M. Bilayet' 'Jalal, Mahbubul A. F.' 'van der Helm, Dick' _chemical_name_common 'Asperchrome A' _chemical_formula_moiety ' C41 H64 Fe N9 O16, 14.0(H2 O)' _chemical_formula_sum 'C41 H92 Fe N9 O30' _chemical_formula_iupac '[Fe (C41 H64 N9 O16)], 14H2 O1' _chemical_formula_weight 1247.07 _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 19.903(6) _cell_length_b 13.757(5) _cell_length_c 10.966(4) _cell_angle_alpha 90 _cell_angle_beta 90.39(2) _cell_angle_gamma 90 _cell_volume 3002.5(18) _cell_formula_units_Z 2 _cell_measurement_temperature 163(2) _exptl_crystal_density_diffrn 1.379 _diffrn_ambient_temperature 163(2) _refine_ls_R_factor_obs .0648 _refine_ls_wR_factor_obs .1628 loop_ _atom_site_label _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_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol Fe1 .39748(4) .24957(7) 1.01011(7) .0146(2) Uani d . 1 . Fe O11 .3091(2) .2516(4) .9201(4) .0186(8) Uani d . 1 . O O12 .4225(2) .3225(3) .8565(4) .0184(9) Uani d . 1 . O O21 .4071(2) .1124(3) .9554(4) .0190(9) Uani d . 1 . O O22 .4925(2) .2191(3) 1.0600(4) .0203(10) Uani d . 1 . O O31 .3543(2) .2078(3) 1.1629(4) .0177(9) Uani d . 1 . O O32 .3853(2) .3782(3) 1.0983(4) .0205(10) Uani d . 1 . O N1 .2464(3) -.0479(4) .5905(5) .0204(12) Uani d . 1 . N H1A .2059(3) -.0534(4) .6164(5) .024 Uiso calc R 1 . H C101 .2987(3) -.0211(5) .6767(5) .0157(13) Uani d . 1 . C H10A .3400(3) -.0546(5) .6524(5) .019 Uiso calc R 1 . H C102 .2780(3) -.0612(5) .8023(5) .0147(12) Uani d . 1 . C O1 .2335(2) -.1233(4) .8097(4) .0224(10) Uani d . 1 . O C103 .3132(3) .0887(5) .6766(6) .0188(13) Uani d . 1 . C H10B .3496(3) .1025(5) .7334(6) .023 Uiso calc R 1 . H H10C .3275(3) .1084(5) .5959(6) .023 Uiso calc R 1 . H C104 .2518(3) .1462(5) .7123(6) .0204(13) Uani d . 1 . C H10D .2369(3) .1245(5) .7918(6) .025 Uiso calc R 1 . H H10E .2160(3) .1329(5) .6542(6) .025 Uiso calc R 1 . H C105 .2640(3) .2566(6) .7169(6) .0223(13) Uani d . 1 . C H10F .2751(3) .2798(6) .6360(6) .027 Uiso calc R 1 . H H10G .2232(3) .2890(6) .7423(6) .027 Uiso calc R 1 . H N11 .3183(3) .2811(4) .8010(5) .0175(11) Uani d . 1 . N C107 .3775(3) .3174(5) .7738(6) .0173(13) Uani d . 1 . C C108 .3897(3) .3524(5) .6467(6) .0221(14) Uani d . 1 . C H10H .3558(3) .3882(5) .6089(6) .027 Uiso calc R 1 . H C109 .4448(4) .3362(5) .5844(6) .0230(14) Uani d . 1 . C C110 .5038(4) .2777(7) .6276(7) .039(2) Uani d . 1 . C H11A .5375(4) .2765(7) .5653(7) .059 Uiso calc R 1 . H H11B .4896(4) .2124(7) .6449(7) .059 Uiso calc R 1 . H H11C .5221(4) .3065(7) .7002(7) .059 Uiso calc R 1 . H C111 .4523(4) .3759(6) .4560(6) .031(2) Uani d . 1 . C H11D .4674(4) .3238(6) .4032(6) .037 Uiso calc R 1 . H H11E .4085(4) .3968(6) .4267(6) .037 Uiso calc R 1 . H C112 .5007(5) .4600(8) .4460(8) .045(2) Uani d . 1 . C H11F .5441(5) .4414(8) .4795(8) .054 Uiso calc R 1 . H H11G .5067(5) .4771(8) .3609(8) .054 Uiso calc R 1 . H O112 .4749(3) .5420(5) .5116(6) .044(2) Uani d . 1 . O H11H .4384(3) .5577(5) .4827(6) .066 Uiso calc R 1 . H N2 .3120(3) -.0301(4) .8998(4) .0154(11) Uani d . 1 . N H2A .3434(3) .0124(4) .8926(4) .018 Uiso calc R 1 . H C201 .2947(3) -.0700(5) 1.0205(5) .0169(13) Uani d . 1 . C H20A .2922(3) -.1409(5) 1.0136(5) .020 Uiso calc R 1 . H C202 .2260(3) -.0326(5) 1.0621(6) .0184(13) Uani d . 1 . C O2 .1839(3) -.0873(4) 1.1070(5) .0259(11) Uani d . 1 . O C203 .3477(3) -.0450(5) 1.1172(5) .0194(13) Uani d . 1 . C H20B .3319(3) -.0682(5) 1.1954(5) .023 Uiso calc R 1 . H H20C .3511(3) .0252(5) 1.1224(5) .023 Uiso calc R 1 . H C204 .4183(3) -.0861(5) 1.0965(6) .0207(14) Uani d . 1 . C H20D .4138(3) -.1544(5) 1.0764(6) .025 Uiso calc R 1 . H H20E .4427(3) -.0823(5) 1.1733(6) .025 Uiso calc R 1 . H C205 .4619(3) -.0383(5) .9977(6) .0213(14) Uani d . 1 . C H20H .5076(3) -.0622(5) 1.0054(6) .026 Uiso calc R 1 . H H20F .4450(3) -.0572(5) .9180(6) .026 Uiso calc R 1 . H N21 .4625(3) .0691(4) 1.0062(5) .0178(11) Uani d . 1 . N C207 .5069(3) .1272(5) 1.0585(5) .0182(13) Uani d . 1 . C C208 .5706(3) .0893(5) 1.1045(6) .0209(14) Uani d . 1 . C H20G .5803(3) .0247(5) 1.0867(6) .025 Uiso calc R 1 . H C209 .6163(4) .1380(6) 1.1696(6) .0237(15) Uani d . 1 . C C210 .6087(4) .2387(6) 1.2192(7) .033(2) Uani d . 1 . C H21A .6488(4) .2566(6) 1.2627(7) .049 Uiso calc R 1 . H H21B .5711(4) .2407(6) 1.2736(7) .049 Uiso calc R 1 . H H21C .6013(4) .2833(6) 1.1532(7) .049 Uiso calc R 1 . H C211 .6837(4) .0896(6) 1.1952(7) .029(2) Uani d . 1 . C H21D .6803(4) .0211(6) 1.1751(7) .035 Uiso calc R 1 . H H21E .6937(4) .0946(6) 1.2817(7) .035 Uiso calc R 1 . H C212 .7415(4) .1342(7) 1.1236(8) .037(2) Uani d . 1 . C H21F .7426(4) .2038(7) 1.1378(8) .044 Uiso calc R 1 . H H21G .7837(4) .1070(7) 1.1525(8) .044 Uiso calc R 1 . H O212 .7345(3) .1160(5) .9947(5) .0399(13) Uani d . 1 . O H21H .7662(3) .1406(5) .9585(5) .060 Uiso calc R 1 . H N3 .2157(3) .0640(4) 1.0515(5) .0198(12) Uani d . 1 . N H3A .2424(3) .0974(4) 1.0067(5) .024 Uiso calc R 1 . H C301 .1608(3) .1138(5) 1.1135(6) .0212(14) Uani d . 1 . C H30A .1438(3) .0696(5) 1.1762(6) .025 Uiso calc R 1 . H C302 .1020(3) .1396(5) 1.0297(6) .0214(14) Uani d . 1 . C O3 .0529(2) .1828(4) 1.0730(5) .0281(12) Uani d . 1 . O C303 .1897(4) .2039(5) 1.1794(6) .0216(14) Uani d . 1 . C H30B .2152(4) .2424(5) 1.1220(6) .026 Uiso calc R 1 . H H30C .1529(4) .2436(5) 1.2089(6) .026 Uiso calc R 1 . H C304 .2348(3) .1755(5) 1.2862(6) .0221(14) Uani d . 1 . C H30D .2609(3) .1189(5) 1.2636(6) .026 Uiso calc R 1 . H H30E .2069(3) .1575(5) 1.3548(6) .026 Uiso calc R 1 . H C305 .2823(3) .2563(6) 1.3254(5) .0201(12) Uani d . 1 . C H30F .2566(3) .3121(6) 1.3526(5) .024 Uiso calc R 1 . H H30G .3100(3) .2342(6) 1.3931(5) .024 Uiso calc R 1 . H N31 .3255(3) .2849(4) 1.2234(5) .0161(11) Uani d . 1 . N C307 .3437(3) .3726(5) 1.1868(5) .0182(13) Uani d . 1 . C C308 .3124(3) .4579(5) 1.2429(6) .0214(14) Uani d . 1 . C H30H .2704(3) .4480(5) 1.2773(6) .026 Uiso calc R 1 . H C309 .3370(4) .5479(6) 1.2506(6) .025(2) Uani d . 1 . C C310 .4054(4) .5791(6) 1.2058(8) .037(2) Uani d . 1 . C H31A .4116(4) .6471(6) 1.2215(8) .056 Uiso calc R 1 . H H31B .4083(4) .5673(6) 1.1197(8) .056 Uiso calc R 1 . H H31C .4396(4) .5426(6) 1.2476(8) .056 Uiso calc R 1 . H C311 .2950(4) .6268(6) 1.3127(7) .032(2) Uani d . 1 . C H31D .2906(4) .6820(6) 1.2584(7) .039 Uiso calc R 1 . H H31E .2503(4) .6016(6) 1.3282(7) .039 Uiso calc R 1 . H C312 .3262(4) .6598(6) 1.4312(7) .033(2) Uani d . 1 . C H31F .3689(4) .6910(6) 1.4148(7) .040 Uiso calc R 1 . H H31G .2971(4) .7074(6) 1.4691(7) .040 Uiso calc R 1 . H O312 .3366(3) .5817(5) 1.5124(5) .0410(14) Uani d . 1 . O H31H .3005(3) .5558(5) 1.5276(5) .062 Uiso calc R 1 . H N4 .1053(3) .1118(5) .9142(5) .0221(12) Uani d . 1 . N H4A .1422(3) .0866(5) .8889(5) .027 Uiso calc R 1 . H C401 .0497(3) .1215(5) .8275(6) .0211(14) Uani d . 1 . C H40A .0084(3) .0992(5) .8670(6) .025 Uiso calc R 1 . H C402 .0655(3) .0522(5) .7223(6) .0215(14) Uani d . 1 . C O4 .1184(2) .0029(4) .7225(4) .0242(10) Uani d . 1 . O C403 .0392(4) .2249(6) .7851(7) .032(2) Uani d . 1 . C H40B -.0014(4) .2280(6) .7358(7) .038 Uiso calc R 1 . H H40C .0327(4) .2662(6) .8557(7) .038 Uiso calc R 1 . H O42 .0933(3) .2612(4) .7166(5) .0310(11) Uani d . 1 . O H42A .0986(3) .2273(4) .6559(5) .046 Uiso calc R 1 . H N5 .0209(3) .0476(5) .6315(5) .0218(12) Uani d . 1 . N H5A -.0133(3) .0859(5) .6306(5) .026 Uiso calc R 1 . H C501 .0304(3) -.0239(6) .5321(6) .0219(14) Uani d . 1 . C H50A .0262(3) -.0899(6) .5647(6) .026 Uiso calc R 1 . H C502 .0982(3) -.0117(5) .4745(6) .0216(14) Uani d . 1 . C O5 .1200(3) .0690(4) .4408(5) .0297(12) Uani d . 1 . O C503 -.0226(4) -.0077(6) .4318(7) .029(2) Uani d . 1 . C H50B -.0666(4) -.0149(6) .4656(7) .044 Uiso calc R 1 . H H50C -.0164(4) -.0547(6) .3681(7) .044 Uiso calc R 1 . H H50D -.0178(4) .0566(6) .3989(7) .044 Uiso calc R 1 . H N6 .1330(3) -.0925(5) .4574(5) .0235(12) Uani d . 1 . N H6A .1169(3) -.1467(5) .4829(5) .028 Uiso calc R 1 . H C601 .1983(4) -.0924(6) .3965(6) .027(2) Uani d . 1 . C H60A .1958(4) -.0479(6) .3280(6) .032 Uiso calc R 1 . H H60B .2062(4) -.1569(6) .3639(6) .032 Uiso calc R 1 . H C602 .2581(4) -.0642(5) .4752(6) .0225(14) Uani d . 1 . C O6 .3149(3) -.0566(5) .4272(4) .0351(13) Uani d . 1 . O O1W .1221(3) .4824(6) .1308(8) .064(2) Uani d . 1 . O O2W .5884(3) .5881(5) .6404(6) .048(2) Uani d . 1 . O O3W .9219(3) .0836(6) .1097(7) .055(2) Uani d . 1 . O O4W .0629(3) .2473(5) .4701(5) .0349(11) Uani d . 1 . O O5W .9219(3) .2349(5) .4380(7) .052(2) Uani d . 1 . O O6W .8916(3) .2789(5) .1948(7) .053(2) Uani d . 1 . O O7W .0113(4) .3685(6) .1152(8) .066(2) Uani d . 1 . O O8W .1431(3) .3938(5) .3708(6) .050(2) Uani d . 1 . O O9W .2271(3) .4156(4) -.0182(5) .0281(11) Uani d . 1 . O O10W .8502(3) -.0604(4) .2243(5) .0324(12) Uani d . 1 . O O11W .2241(3) .4596(6) 1.5582(6) .056(2) Uani d . 1 . O O12W .8872(3) .1225(5) .6478(7) .054(2) Uani d . 1 . O O13W .1614(4) -.2895(6) 1.1410(7) .065(2) Uani d . 1 . O O14W .0351(3) -.0551(6) 1.1092(8) .060(2) Uani d . 1 . O loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Fe1 .0191(4) .0113(4) .0132(4) -.0004(4) .0008(3) .0002(4) O11 .020(2) .018(2) .017(2) .000(2) -.002(2) .001(2) O12 .023(2) .016(2) .016(2) -.003(2) -.002(2) .000(2) O21 .027(2) .012(2) .018(2) .005(2) -.004(2) .001(2) O22 .022(2) .015(2) .023(2) .000(2) -.002(2) .000(2) O31 .026(2) .011(2) .016(2) -.003(2) .006(2) .000(2) O32 .031(2) .012(2) .019(2) .000(2) .003(2) -.003(2) N1 .029(3) .020(3) .012(2) -.001(2) -.001(2) .000(2) C101 .027(3) .015(3) .005(2) .001(3) .002(2) -.001(2) C102 .013(3) .016(3) .015(3) .003(2) .000(2) .001(2) O1 .028(2) .017(2) .022(2) -.003(2) -.001(2) .004(2) C103 .022(3) .018(3) .016(3) -.004(3) .002(2) -.001(3) C104 .023(3) .017(3) .022(3) -.003(3) .000(3) -.001(3) C105 .023(3) .019(3) .026(3) .003(3) -.004(2) -.001(3) N11 .024(3) .013(3) .016(2) .004(2) -.002(2) .003(2) C107 .028(3) .008(3) .016(3) .007(3) .002(2) .000(2) C108 .026(3) .019(3) .022(3) .001(3) -.004(3) .004(3) C109 .032(4) .020(4) .017(3) .004(3) .001(3) -.005(3) C110 .042(4) .046(6) .030(4) .025(4) -.004(3) -.007(4) C111 .037(4) .033(4) .023(3) .004(4) .010(3) -.003(3) C112 .042(5) .057(6) .036(4) .009(5) .011(4) .015(4) O112 .045(3) .037(4) .051(4) .001(3) -.006(3) .010(3) N2 .025(3) .009(3) .013(2) -.002(2) .000(2) .002(2) C201 .024(3) .013(3) .013(3) -.003(3) -.001(2) .001(2) C202 .021(3) .017(3) .017(3) -.006(3) -.001(2) .000(3) O2 .032(3) .019(3) .027(2) -.007(2) .009(2) -.001(2) C203 .026(3) .019(3) .013(3) .001(3) .002(2) .000(3) C204 .025(3) .016(3) .020(3) .005(3) -.004(3) .004(3) C205 .028(3) .011(3) .025(3) .001(3) .000(3) -.006(3) N21 .017(3) .010(3) .026(3) .006(2) -.002(2) .000(2) C207 .024(3) .019(3) .012(3) -.001(3) .005(2) .000(2) C208 .024(3) .014(3) .024(3) .001(3) -.004(3) .004(3) C209 .028(4) .024(4) .019(3) .001(3) -.002(3) .006(3) C210 .034(4) .023(4) .041(4) .008(3) -.013(3) -.005(4) C211 .031(4) .026(4) .029(4) .003(3) -.005(3) -.002(3) C212 .038(4) .031(5) .041(4) .006(4) -.001(3) -.001(4) O212 .047(3) .036(3) .037(3) .005(3) .010(2) .002(3) N3 .020(3) .016(3) .023(3) -.003(2) .006(2) -.003(2) C301 .017(3) .021(4) .026(3) -.002(3) .003(2) -.003(3) C302 .023(3) .016(3) .025(3) -.003(3) -.001(3) -.002(3) O3 .017(2) .035(3) .032(3) .004(2) .003(2) -.013(2) C303 .028(3) .012(3) .025(3) -.001(3) .002(3) -.004(3) C304 .026(3) .016(3) .024(3) -.003(3) .003(3) .001(3) C305 .027(3) .021(3) .012(3) -.005(3) .006(2) .000(3) N31 .024(3) .013(3) .011(2) -.002(2) .006(2) -.002(2) C307 .021(3) .021(3) .012(3) -.006(3) -.002(2) -.005(3) C308 .022(3) .018(3) .024(3) -.003(3) .008(3) -.004(3) C309 .031(4) .026(4) .020(3) .000(3) .003(3) -.002(3) C310 .047(5) .025(4) .040(4) -.013(4) .012(4) -.005(4) C311 .039(4) .025(4) .033(4) .000(3) .003(3) -.003(3) C312 .033(4) .034(5) .032(4) -.002(3) .010(3) -.007(3) O312 .045(3) .050(4) .028(3) -.010(3) .003(2) -.002(3) N4 .019(3) .028(3) .019(3) -.002(2) .005(2) -.004(2) C401 .020(3) .023(4) .020(3) -.003(3) .000(2) .003(3) C402 .024(3) .014(3) .027(3) -.006(3) .005(3) .001(3) O4 .031(3) .021(3) .020(2) .001(2) -.002(2) .001(2) C403 .036(4) .024(4) .035(4) .004(3) -.004(3) .000(3) O42 .037(3) .025(3) .031(2) -.004(3) -.004(2) .000(2) N5 .020(3) .023(3) .022(3) -.001(2) .005(2) .000(2) C501 .022(3) .023(4) .021(3) -.007(3) .002(3) -.004(3) C502 .023(3) .028(4) .013(3) -.005(3) -.003(2) -.003(3) O5 .037(3) .016(3) .036(3) -.005(2) .012(2) .009(2) C503 .023(3) .035(5) .029(4) -.005(3) .003(3) -.001(3) N6 .032(3) .020(3) .019(3) -.003(3) -.003(2) -.006(2) C601 .035(4) .025(4) .020(3) .006(3) -.002(3) -.011(3) C602 .035(4) .016(3) .017(3) .008(3) -.006(3) -.005(3) O6 .037(3) .053(4) .015(2) .004(3) .002(2) -.005(2) O1W .037(3) .063(5) .092(5) -.009(3) .024(4) -.033(4) O2W .048(3) .053(4) .042(3) -.002(3) -.011(3) .000(3) O3W .046(4) .059(5) .061(4) -.013(4) .009(3) -.003(4) O4W .043(3) .027(3) .034(3) .001(3) .002(2) .001(3) O5W .052(4) .028(4) .075(4) .006(3) -.008(3) -.010(3) O6W .037(3) .040(4) .082(5) .008(3) -.007(3) -.009(3) O7W .050(4) .056(5) .093(6) .013(4) .001(4) -.010(4) O8W .057(4) .038(4) .055(4) -.003(3) .023(3) -.010(3) O9W .035(3) .022(3) .027(3) .005(2) -.003(2) -.003(2) O10W .036(3) .027(3) .034(3) -.003(2) -.010(2) .000(2) O11W .054(4) .067(5) .046(4) -.013(4) -.012(3) .029(4) O12W .035(3) .041(4) .084(5) .004(3) .008(3) .005(4) O13W .086(5) .041(4) .069(5) .015(4) .022(4) .009(4) O14W .047(4) .048(4) .085(5) -.004(3) .012(4) -.001(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Fe1 O31 . 1.974(4) yes Fe1 O21 . 1.989(5) yes Fe1 O22 . 2.010(5) yes Fe1 O11 . 2.012(4) yes Fe1 O12 . 2.026(4) yes Fe1 O32 . 2.031(5) yes O11 N11 . 1.380(7) yes O12 C107 . 1.271(8) yes O21 N21 . 1.368(7) yes O22 C207 . 1.296(9) yes O31 N31 . 1.377(7) yes O32 C307 . 1.282(8) yes N1 C602 . 1.307(8) yes N1 C101 . 1.449(8) yes C101 C103 . 1.538(9) yes C101 C102 . 1.543(8) yes C102 O1 . 1.233(8) yes C102 N2 . 1.332(8) yes C103 C104 . 1.510(9) no C104 C105 . 1.538(11) no C105 N11 . 1.456(8) yes N11 C107 . 1.316(9) yes C107 C108 . 1.496(9) no C108 C109 . 1.316(10) no C109 C110 . 1.498(10) no C109 C111 . 1.518(10) no C111 C112 . 1.511(13) no C112 O112 . 1.435(12) no N2 C201 . 1.476(8) yes C201 C202 . 1.534(9) yes C201 C203 . 1.529(9) yes C202 O2 . 1.231(8) yes C202 N3 . 1.349(9) yes C203 C204 . 1.534(9) no C204 C205 . 1.540(9) no C205 N21 . 1.481(9) yes N21 C207 . 1.319(9) yes C207 C208 . 1.458(9) no C208 C209 . 1.333(10) no C209 C210 . 1.496(11) no C209 C211 . 1.522(10) no C211 C212 . 1.527(11) no C212 O212 . 1.441(10) no N3 C301 . 1.462(8) yes C301 C302 . 1.524(9) yes C301 C303 . 1.543(9) yes C302 O3 . 1.241(8) yes C302 N4 . 1.325(9) yes C303 C304 . 1.522(10) no C304 C305 . 1.521(10) no C305 N31 . 1.468(7) yes N31 C307 . 1.323(9) yes C307 C308 . 1.466(10) no C308 C309 . 1.334(11) no C309 C310 . 1.512(10) no C309 C311 . 1.532(11) no C311 C312 . 1.506(11) no C312 O312 . 1.410(11) no N4 C401 . 1.460(8) yes C401 C403 . 1.511(10) yes C401 C402 . 1.531(10) yes C402 O4 . 1.252(9) yes C402 N5 . 1.330(9) yes C403 O42 . 1.409(9) yes N5 C501 . 1.481(9) yes C501 C502 . 1.504(9) yes C501 C503 . 1.535(9) yes C502 O5 . 1.249(9) yes C502 N6 . 1.323(10) yes N6 C601 . 1.464(9) yes C601 C602 . 1.517(10) yes C602 O6 . 1.254(9) yes _cod_database_code 2006192