Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_spirnos _database_code_CSD 147145 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Eichen, Yoav' 'Godsi, Oded' 'Natan, Ezra' 'Peskin, Uri' _publ_contact_author_name 'Dr Yoav Eichen' _publ_contact_author_address ; Dr Yoav Eichen Department of Chemistry Technion - Israel Institute of Technology Technion City Haifa 32000 ISRAEL ; _publ_contact_author_email 'CHRYOAV@TX.TECHNION.AC.IL' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 1',3'-dihydro-1'-(n-propyl)-3',3'dimethyl-6-nitrospiro-[2H-13-benzopyran- 2,2'-(2H)-indoline] ; _chemical_melting_point 150.7 _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 N2 O3' _chemical_formula_weight 350.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.1910(5) _cell_length_b 12.4340(5) _cell_length_c 12.9160(4) _cell_angle_alpha 101.743(2) _cell_angle_beta 104.914(2) _cell_angle_gamma 90.647(2) _cell_volume 1848.09(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7753 _cell_measurement_theta_min 1.67 _cell_measurement_theta_max 27.5 _exptl_crystal_description 'prisms' _exptl_crystal_colour 'transparent' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6532 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0593 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.05 _reflns_number_total 6532 _reflns_number_gt 3935 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius(1997). KappaCCD Server Software.' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997).' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997).' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Molecular Structure Corporation (1999). ORTEP. TEXRAY Structure Analysis Package. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0599P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.026(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 6532 _refine_ls_number_parameters 646 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1080 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_restrained_S_all 0.934 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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 C1A C 0.73136(14) 0.06778(13) 0.25223(13) 0.0485(4) Uani 1 1 d . . . C2A C 0.67426(18) -0.03175(15) 0.23864(17) 0.0626(5) Uani 1 1 d . . . C3A C 0.6942(2) -0.08457(19) 0.3267(2) 0.0785(7) Uani 1 1 d . . . C4A C 0.7700(2) -0.03786(18) 0.42411(19) 0.0737(6) Uani 1 1 d . . . C5A C 0.82844(18) 0.06196(17) 0.43922(16) 0.0621(5) Uani 1 1 d . . . C6A C 0.80876(15) 0.11464(13) 0.35255(13) 0.0487(4) Uani 1 1 d . . . N7A N 0.85871(12) 0.21384(11) 0.34569(11) 0.0495(4) Uani 1 1 d . . . C8A C 0.92132(18) 0.29324(16) 0.44364(16) 0.0608(5) Uani 1 1 d . . . C9A C 1.0464(2) 0.2771(2) 0.4766(2) 0.0829(7) Uani 1 1 d . . . C10A C 1.1094(3) 0.3570(3) 0.5806(2) 0.0991(9) Uani 1 1 d . . . C11A C 0.78969(14) 0.25059(13) 0.25273(13) 0.0471(4) Uani 1 1 d . . . O12A O 0.69928(10) 0.31090(9) 0.29295(9) 0.0543(3) Uani 1 1 d . . . C13A C 0.65147(15) 0.39469(12) 0.24847(13) 0.0467(4) Uani 1 1 d . . . C14A C 0.55133(16) 0.42862(14) 0.27142(15) 0.0526(4) Uani 1 1 d . . . C15A C 0.49818(18) 0.51299(15) 0.22819(15) 0.0590(5) Uani 1 1 d . . . C16A C 0.54837(17) 0.56321(13) 0.16470(14) 0.0579(5) Uani 1 1 d . . . N17A N 0.49408(19) 0.65407(14) 0.11906(15) 0.0787(5) Uani 1 1 d . . . O18A O 0.54347(18) 0.70359(15) 0.07058(18) 0.1218(7) Uani 1 1 d . . . O19A O 0.39959(19) 0.67502(15) 0.13008(16) 0.1198(7) Uani 1 1 d . . . C20A C 0.65044(17) 0.53285(14) 0.14314(15) 0.0573(5) Uani 1 1 d . . . C21A C 0.70357(15) 0.44674(13) 0.18564(14) 0.0500(4) Uani 1 1 d . . . C22A C 0.81262(16) 0.41077(15) 0.17140(16) 0.0580(5) Uani 1 1 d . . . C23A C 0.85439(16) 0.32297(14) 0.20671(15) 0.0548(5) Uani 1 1 d . . . C24A C 0.73325(14) 0.14106(13) 0.17234(13) 0.0472(4) Uani 1 1 d . . . C25A C 0.61755(18) 0.15378(19) 0.09821(18) 0.0642(5) Uani 1 1 d . . . C26A C 0.81212(19) 0.09343(18) 0.10139(17) 0.0597(5) Uani 1 1 d . . . C1B C 0.23226(15) 0.32460(13) 0.24818(14) 0.0498(4) Uani 1 1 d . . . C2B C 0.17467(19) 0.41614(15) 0.23128(18) 0.0655(5) Uani 1 1 d . . . C3B C 0.1931(2) 0.50839(18) 0.3161(2) 0.0825(7) Uani 1 1 d . . . C4B C 0.2679(2) 0.50819(18) 0.4146(2) 0.0789(7) Uani 1 1 d . . . C5B C 0.32840(19) 0.41697(16) 0.43379(17) 0.0635(5) Uani 1 1 d . . . C6B C 0.30858(15) 0.32522(13) 0.34847(13) 0.0493(4) Uani 1 1 d . . . N7B N 0.35947(12) 0.22435(11) 0.34626(10) 0.0491(4) Uani 1 1 d . . . C8B C 0.42010(18) 0.19108(18) 0.44625(16) 0.0602(5) Uani 1 1 d . . . C9B C 0.5463(2) 0.2211(3) 0.4786(2) 0.0865(7) Uani 1 1 d . . . C10B C 0.6092(3) 0.1880(3) 0.5825(2) 0.1008(9) Uani 1 1 d . . . C11B C 0.28982(14) 0.14435(13) 0.25579(13) 0.0450(4) Uani 1 1 d . . . O12B O 0.19990(9) 0.10253(8) 0.29926(9) 0.0492(3) Uani 1 1 d . . . C13B C 0.15206(14) -0.00147(12) 0.25904(12) 0.0439(4) Uani 1 1 d . . . C14B C 0.05003(16) -0.02432(16) 0.28097(15) 0.0541(5) Uani 1 1 d . . . C15B C -0.00369(19) -0.12822(16) 0.24031(16) 0.0613(5) Uani 1 1 d . . . C16B C 0.04719(18) -0.20736(14) 0.18138(14) 0.0612(5) Uani 1 1 d . . . N17B N -0.0116(2) -0.31646(16) 0.13455(16) 0.0894(6) Uani 1 1 d . . . O18B O 0.0345(2) -0.38636(15) 0.0834(2) 0.1432(8) Uani 1 1 d . . . O19B O -0.1069(2) -0.33063(15) 0.14591(17) 0.1294(8) Uani 1 1 d . . . C20B C 0.15104(19) -0.18698(14) 0.16291(15) 0.0582(5) Uani 1 1 d . . . C21B C 0.20528(15) -0.08267(13) 0.20167(12) 0.0482(4) Uani 1 1 d . . . C22B C 0.31530(16) -0.05227(15) 0.18879(14) 0.0537(5) Uani 1 1 d . . . C23B C 0.35490(17) 0.05097(15) 0.21571(14) 0.0520(4) Uani 1 1 d . . . C24B C 0.23257(14) 0.21469(13) 0.17159(13) 0.0462(4) Uani 1 1 d . . . C25B C 0.30795(19) 0.22878(18) 0.09631(17) 0.0582(5) Uani 1 1 d . . . C26B C 0.11463(17) 0.16754(19) 0.10241(18) 0.0594(5) Uani 1 1 d . . . H2A H 0.6157(16) -0.0683(14) 0.1661(15) 0.068(5) Uiso 1 1 d . . . H3A H 0.6509(19) -0.1495(18) 0.3157(17) 0.093(7) Uiso 1 1 d . . . H4A H 0.7799(18) -0.0778(17) 0.4833(17) 0.090(7) Uiso 1 1 d . . . H5A H 0.8828(16) 0.0960(15) 0.5079(15) 0.067(6) Uiso 1 1 d . . . H8C H 0.8886(16) 0.2886(15) 0.5034(15) 0.071(6) Uiso 1 1 d . . . H8D H 0.9154(18) 0.3679(18) 0.4288(16) 0.090(7) Uiso 1 1 d . . . H9C H 1.080(3) 0.286(2) 0.419(2) 0.136(11) Uiso 1 1 d . . . H9D H 1.049(3) 0.203(3) 0.492(2) 0.152(13) Uiso 1 1 d . . . H10C H 1.096(3) 0.434(3) 0.565(3) 0.172(14) Uiso 1 1 d . . . H10D H 1.068(2) 0.356(2) 0.638(2) 0.127(10) Uiso 1 1 d . . . H10E H 1.190(3) 0.339(2) 0.600(2) 0.152(13) Uiso 1 1 d . . . H14A H 0.5154(14) 0.3929(13) 0.3147(13) 0.056(5) Uiso 1 1 d . . . H15A H 0.4282(18) 0.5307(15) 0.2423(15) 0.073(6) Uiso 1 1 d . . . H20A H 0.6863(16) 0.5715(15) 0.0935(15) 0.078(6) Uiso 1 1 d . . . H22A H 0.8579(16) 0.4527(14) 0.1360(14) 0.068(5) Uiso 1 1 d . . . H23A H 0.9312(17) 0.3007(14) 0.2011(14) 0.067(5) Uiso 1 1 d . . . H25C H 0.5869(15) 0.0821(15) 0.0496(14) 0.063(5) Uiso 1 1 d . . . H25D H 0.5632(19) 0.1757(16) 0.1404(16) 0.082(7) Uiso 1 1 d . . . H25E H 0.6322(18) 0.2101(17) 0.0506(16) 0.090(7) Uiso 1 1 d . . . H26C H 0.8241(16) 0.1459(15) 0.0538(15) 0.077(6) Uiso 1 1 d . . . H26D H 0.7805(19) 0.0172(19) 0.0544(18) 0.097(7) Uiso 1 1 d . . . H26E H 0.8969(19) 0.0830(15) 0.1497(16) 0.080(6) Uiso 1 1 d . . . H2B H 0.1283(16) 0.4187(14) 0.1612(15) 0.063(6) Uiso 1 1 d . . . H3B H 0.152(2) 0.569(2) 0.298(2) 0.123(9) Uiso 1 1 d . . . H4B H 0.2809(18) 0.5672(18) 0.4712(17) 0.088(7) Uiso 1 1 d . . . H5B H 0.3829(15) 0.4173(13) 0.4991(14) 0.053(5) Uiso 1 1 d . . . H8F H 0.3876(15) 0.2241(14) 0.5070(15) 0.064(5) Uiso 1 1 d . . . H8G H 0.4069(16) 0.1134(16) 0.4369(14) 0.074(6) Uiso 1 1 d . . . H9F H 0.554(3) 0.304(3) 0.493(3) 0.196(16) Uiso 1 1 d . . . H9G H 0.576(2) 0.191(2) 0.419(2) 0.118(10) Uiso 1 1 d . . . H10F H 0.579(2) 0.225(2) 0.635(2) 0.114(11) Uiso 1 1 d . . . H10G H 0.588(3) 0.113(2) 0.578(2) 0.133(12) Uiso 1 1 d . . . H10H H 0.699(3) 0.227(3) 0.614(3) 0.181(14) Uiso 1 1 d . . . H14B H 0.0183(15) 0.0318(15) 0.3181(14) 0.061(5) Uiso 1 1 d . . . H15B H -0.0732(18) -0.1406(14) 0.2547(14) 0.070(6) Uiso 1 1 d . . . H20B H 0.1842(15) -0.2436(14) 0.1253(13) 0.058(5) Uiso 1 1 d . . . H22B H 0.3537(15) -0.1164(14) 0.1569(13) 0.061(5) Uiso 1 1 d . . . H23B H 0.4228(15) 0.0716(13) 0.2084(13) 0.052(5) Uiso 1 1 d . . . H25F H 0.3858(18) 0.2608(14) 0.1374(14) 0.067(6) Uiso 1 1 d . . . H25G H 0.2684(17) 0.2793(16) 0.0480(16) 0.081(6) Uiso 1 1 d . . . H25H H 0.3138(15) 0.1613(15) 0.0501(14) 0.062(5) Uiso 1 1 d . . . H26F H 0.0850(17) 0.2155(16) 0.0526(16) 0.078(6) Uiso 1 1 d . . . H26G H 0.1171(16) 0.0954(16) 0.0563(15) 0.073(6) Uiso 1 1 d . . . H26H H 0.0666(18) 0.1656(16) 0.1502(16) 0.079(6) Uiso 1 1 d . . . 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 C1A 0.0464(11) 0.0492(10) 0.0542(10) 0.0169(8) 0.0166(8) 0.0080(8) C2A 0.0635(13) 0.0563(11) 0.0705(13) 0.0198(10) 0.0176(11) -0.0037(10) C3A 0.0861(17) 0.0670(14) 0.0939(17) 0.0367(13) 0.0296(14) -0.0042(13) C4A 0.0832(16) 0.0773(15) 0.0757(15) 0.0424(13) 0.0273(13) 0.0123(12) C5A 0.0671(14) 0.0683(13) 0.0569(12) 0.0244(10) 0.0180(11) 0.0135(11) C6A 0.0498(11) 0.0491(10) 0.0516(10) 0.0157(8) 0.0171(9) 0.0119(8) N7A 0.0483(9) 0.0467(8) 0.0508(8) 0.0126(6) 0.0066(7) 0.0057(7) C8A 0.0642(14) 0.0546(12) 0.0560(12) 0.0020(9) 0.0102(10) 0.0077(10) C9A 0.0634(15) 0.0911(18) 0.0724(15) -0.0103(13) 0.0013(12) 0.0026(13) C10A 0.087(2) 0.106(2) 0.0789(18) -0.0079(15) -0.0006(16) -0.0146(17) C11A 0.0409(10) 0.0498(9) 0.0570(10) 0.0192(8) 0.0177(8) 0.0119(8) O12A 0.0577(8) 0.0511(7) 0.0678(7) 0.0269(6) 0.0294(6) 0.0178(6) C13A 0.0498(11) 0.0388(9) 0.0525(9) 0.0140(8) 0.0118(8) 0.0087(8) C14A 0.0539(12) 0.0511(10) 0.0575(10) 0.0131(8) 0.0217(9) 0.0105(9) C15A 0.0563(13) 0.0564(11) 0.0647(12) 0.0110(9) 0.0177(10) 0.0175(10) C16A 0.0678(13) 0.0434(9) 0.0601(11) 0.0171(8) 0.0077(10) 0.0143(9) N17A 0.0915(15) 0.0641(11) 0.0800(12) 0.0245(9) 0.0138(11) 0.0279(11) O18A 0.1207(16) 0.1050(13) 0.1683(18) 0.0950(14) 0.0362(14) 0.0298(11) O19A 0.1279(16) 0.1221(14) 0.1397(16) 0.0644(12) 0.0572(13) 0.0824(13) C20A 0.0626(13) 0.0460(10) 0.0651(11) 0.0198(9) 0.0140(10) 0.0052(9) C21A 0.0507(11) 0.0423(9) 0.0583(10) 0.0149(8) 0.0140(9) 0.0014(8) C22A 0.0547(12) 0.0543(11) 0.0736(12) 0.0232(10) 0.0249(10) 0.0000(9) C23A 0.0457(11) 0.0547(11) 0.0710(12) 0.0212(9) 0.0219(9) 0.0070(9) C24A 0.0418(10) 0.0514(10) 0.0505(9) 0.0161(8) 0.0118(8) 0.0062(8) C25A 0.0502(13) 0.0705(14) 0.0676(13) 0.0204(11) 0.0037(11) 0.0033(10) C26A 0.0617(14) 0.0651(13) 0.0555(11) 0.0130(10) 0.0211(10) 0.0062(10) C1B 0.0467(10) 0.0477(10) 0.0561(10) 0.0094(8) 0.0170(9) 0.0029(8) C2B 0.0687(14) 0.0542(12) 0.0735(14) 0.0141(10) 0.0177(12) 0.0125(10) C3B 0.0855(18) 0.0539(13) 0.1063(19) 0.0109(13) 0.0266(15) 0.0177(12) C4B 0.0820(17) 0.0527(13) 0.0968(18) -0.0095(12) 0.0345(15) 0.0003(12) C5B 0.0631(14) 0.0603(12) 0.0602(12) -0.0003(10) 0.0150(11) -0.0067(10) C6B 0.0463(10) 0.0477(10) 0.0546(10) 0.0067(8) 0.0182(9) -0.0024(8) N7B 0.0469(9) 0.0492(8) 0.0475(8) 0.0105(6) 0.0058(7) -0.0029(7) C8B 0.0620(13) 0.0636(13) 0.0547(11) 0.0193(10) 0.0101(10) -0.0052(10) C9B 0.0613(15) 0.125(2) 0.0735(16) 0.0446(16) 0.0009(12) -0.0019(14) C10B 0.094(2) 0.128(3) 0.0732(18) 0.0389(18) -0.0051(16) 0.010(2) C11B 0.0376(10) 0.0475(9) 0.0501(9) 0.0087(7) 0.0137(8) -0.0021(7) O12B 0.0504(7) 0.0434(6) 0.0560(7) 0.0042(5) 0.0232(6) -0.0019(5) C13B 0.0462(10) 0.0426(9) 0.0421(9) 0.0121(7) 0.0080(8) 0.0003(8) C14B 0.0510(12) 0.0557(11) 0.0574(11) 0.0154(9) 0.0151(9) 0.0005(9) C15B 0.0577(13) 0.0660(13) 0.0605(11) 0.0255(10) 0.0074(10) -0.0109(10) C16B 0.0751(15) 0.0471(10) 0.0535(10) 0.0186(9) -0.0026(10) -0.0107(10) N17B 0.1095(18) 0.0625(13) 0.0807(13) 0.0207(10) -0.0052(12) -0.0257(13) O18B 0.167(2) 0.0581(11) 0.174(2) -0.0206(12) 0.0277(17) -0.0209(12) O19B 0.1348(18) 0.0986(13) 0.1415(17) 0.0206(12) 0.0200(14) -0.0612(13) C20B 0.0760(15) 0.0427(10) 0.0515(10) 0.0109(8) 0.0084(10) 0.0069(10) C21B 0.0560(11) 0.0416(9) 0.0450(9) 0.0100(7) 0.0093(8) 0.0068(8) C22B 0.0597(12) 0.0499(11) 0.0536(10) 0.0089(8) 0.0197(9) 0.0162(9) C23B 0.0433(11) 0.0581(12) 0.0580(11) 0.0126(8) 0.0192(9) 0.0081(9) C24B 0.0408(10) 0.0496(9) 0.0483(9) 0.0106(7) 0.0117(8) 0.0034(7) C25B 0.0582(14) 0.0628(13) 0.0570(12) 0.0141(10) 0.0204(10) 0.0040(11) C26B 0.0504(12) 0.0645(13) 0.0584(12) 0.0117(11) 0.0071(10) 0.0020(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1A C2A 1.370(2) . ? C1A C6A 1.400(2) . ? C1A C24A 1.513(2) . ? C2A C3A 1.396(3) . ? C3A C4A 1.367(3) . ? C4A C5A 1.377(3) . ? C5A C6A 1.380(2) . ? C6A N7A 1.398(2) . ? N7A C11A 1.439(2) . ? N7A C8A 1.461(2) . ? C8A C9A 1.502(3) . ? C9A C10A 1.513(3) . ? C11A O12A 1.4839(18) . ? C11A C23A 1.493(2) . ? C11A C24A 1.563(2) . ? O12A C13A 1.3566(18) . ? C13A C14A 1.380(2) . ? C13A C21A 1.397(2) . ? C14A C15A 1.378(2) . ? C15A C16A 1.377(3) . ? C16A C20A 1.384(3) . ? C16A N17A 1.466(2) . ? N17A O18A 1.215(2) . ? N17A O19A 1.221(2) . ? C20A C21A 1.393(2) . ? C21A C22A 1.451(2) . ? C22A C23A 1.325(2) . ? C24A C25A 1.517(3) . ? C24A C26A 1.536(2) . ? C1B C2B 1.370(3) . ? C1B C6B 1.385(2) . ? C1B C24B 1.516(2) . ? C2B C3B 1.386(3) . ? C3B C4B 1.362(3) . ? C4B C5B 1.390(3) . ? C5B C6B 1.385(2) . ? C6B N7B 1.404(2) . ? N7B C11B 1.440(2) . ? N7B C8B 1.456(2) . ? C8B C9B 1.508(3) . ? C9B C10B 1.503(3) . ? C11B O12B 1.4866(18) . ? C11B C23B 1.494(2) . ? C11B C24B 1.564(2) . ? O12B C13B 1.3549(18) . ? C13B C14B 1.384(2) . ? C13B C21B 1.395(2) . ? C14B C15B 1.379(3) . ? C15B C16B 1.373(3) . ? C16B C20B 1.377(3) . ? C16B N17B 1.463(3) . ? N17B O18B 1.215(3) . ? N17B O19B 1.223(3) . ? C20B C21B 1.384(2) . ? C21B C22B 1.449(2) . ? C22B C23B 1.311(2) . ? C24B C26B 1.522(2) . ? C24B C25B 1.532(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2A C1A C6A 120.24(16) . . ? C2A C1A C24A 131.23(16) . . ? C6A C1A C24A 108.42(14) . . ? C1A C2A C3A 118.8(2) . . ? C4A C3A C2A 120.4(2) . . ? C3A C4A C5A 121.7(2) . . ? C4A C5A C6A 118.1(2) . . ? C5A C6A N7A 129.33(17) . . ? C5A C6A C1A 120.79(17) . . ? N7A C6A C1A 109.86(13) . . ? C6A N7A C11A 108.70(13) . . ? C6A N7A C8A 121.65(14) . . ? C11A N7A C8A 120.63(14) . . ? N7A C8A C9A 113.50(16) . . ? C8A C9A C10A 112.9(2) . . ? N7A C11A O12A 105.37(12) . . ? N7A C11A C23A 113.49(14) . . ? O12A C11A C23A 110.54(13) . . ? N7A C11A C24A 103.38(12) . . ? O12A C11A C24A 107.92(13) . . ? C23A C11A C24A 115.42(13) . . ? C13A O12A C11A 120.96(12) . . ? O12A C13A C14A 116.95(15) . . ? O12A C13A C21A 121.40(15) . . ? C14A C13A C21A 121.61(15) . . ? C15A C14A C13A 119.78(17) . . ? C16A C15A C14A 118.70(18) . . ? C15A C16A C20A 122.62(16) . . ? C15A C16A N17A 119.62(18) . . ? C20A C16A N17A 117.75(18) . . ? O18A N17A O19A 123.01(19) . . ? O18A N17A C16A 119.1(2) . . ? O19A N17A C16A 117.9(2) . . ? C16A C20A C21A 118.77(17) . . ? C20A C21A C13A 118.48(16) . . ? C20A C21A C22A 123.35(16) . . ? C13A C21A C22A 118.13(15) . . ? C23A C22A C21A 120.27(17) . . ? C22A C23A C11A 123.02(17) . . ? C1A C24A C25A 114.60(15) . . ? C1A C24A C26A 108.16(14) . . ? C25A C24A C26A 109.17(16) . . ? C1A C24A C11A 100.92(13) . . ? C25A C24A C11A 113.63(15) . . ? C26A C24A C11A 110.03(14) . . ? C2B C1B C6B 120.13(17) . . ? C2B C1B C24B 131.03(17) . . ? C6B C1B C24B 108.80(14) . . ? C1B C2B C3B 119.1(2) . . ? C4B C3B C2B 120.5(2) . . ? C3B C4B C5B 121.7(2) . . ? C6B C5B C4B 117.1(2) . . ? C1B C6B C5B 121.48(17) . . ? C1B C6B N7B 110.29(14) . . ? C5B C6B N7B 128.22(18) . . ? C6B N7B C11B 108.03(13) . . ? C6B N7B C8B 121.92(15) . . ? C11B N7B C8B 120.17(14) . . ? N7B C8B C9B 113.43(16) . . ? C10B C9B C8B 113.7(2) . . ? N7B C11B O12B 105.11(11) . . ? N7B C11B C23B 112.65(14) . . ? O12B C11B C23B 109.71(13) . . ? N7B C11B C24B 103.73(12) . . ? O12B C11B C24B 107.91(12) . . ? C23B C11B C24B 116.94(13) . . ? C13B O12B C11B 120.80(11) . . ? O12B C13B C14B 116.84(14) . . ? O12B C13B C21B 121.53(15) . . ? C14B C13B C21B 121.59(15) . . ? C15B C14B C13B 119.40(19) . . ? C16B C15B C14B 119.0(2) . . ? C15B C16B C20B 122.20(17) . . ? C15B C16B N17B 119.1(2) . . ? C20B C16B N17B 118.7(2) . . ? O18B N17B O19B 123.7(2) . . ? O18B N17B C16B 118.7(2) . . ? O19B N17B C16B 117.6(2) . . ? C16B C20B C21B 119.56(18) . . ? C20B C21B C13B 118.19(17) . . ? C20B C21B C22B 124.38(17) . . ? C13B C21B C22B 117.42(15) . . ? C23B C22B C21B 120.73(16) . . ? C22B C23B C11B 123.51(17) . . ? C1B C24B C26B 113.66(15) . . ? C1B C24B C25B 108.58(14) . . ? C26B C24B C25B 109.52(16) . . ? C1B C24B C11B 100.59(12) . . ? C26B C24B C11B 113.22(14) . . ? C25B C24B C11B 110.94(14) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.134 _refine_diff_density_min -0.122 _refine_diff_density_rms 0.027