Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_global _database_code_CSD 168943 _journal_coden_Cambridge 207 loop_ _publ_author_name 'Cave, Gareth W. V.' 'Raston, Colin' _publ_contact_author_name 'Prof Colin Raston' _publ_contact_author_address ; School of Chemistry University of Leeds Leeds West Yorkshire LS2 9JT UNITED KINGDOM ; _publ_contact_author_email 'C.RASTON@CHEM.LEEDS.AC.UK' _publ_reqested_journal 'Perkin Trans 1' _publ_section_title ; Efficient synthesis of pyridines via a sequential solventless aldol condensation and Michael addition ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 4'-(4-butoxyphenyl)-4,2';6',4''-terpyridine ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H23 N3 O' _chemical_formula_weight 381.46 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 10.8889(2) _cell_length_b 14.1687(8) _cell_length_c 14.6071(2) _cell_angle_alpha 117.946(1) _cell_angle_beta 91.825(1) _cell_angle_gamma 96.606(1) _cell_volume 1968.13(12) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9842 _exptl_absorpt_correction_T_max 0.9905 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method 'Phi and Omega scan ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28835 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0771 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 28.30 _reflns_number_total 9549 _reflns_number_gt 6158 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Enraf-Nonius) ' _computing_cell_refinement DENZO _computing_data_reduction DENZO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material ? _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^)+(0.1127P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9549 _refine_ls_number_parameters 525 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1111 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1920 _refine_ls_wR_factor_gt 0.1449 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.33788(12) 0.73761(10) 0.48332(10) 0.0231(3) Uani 1 1 d . . . N3 N 0.02510(14) 1.31498(12) 0.79401(12) 0.0181(4) Uani 1 1 d . . . C7 C -0.00410(17) 1.12060(15) 0.70789(14) 0.0173(4) Uani 1 1 d . . . H7 H -0.0596 1.0549 0.6823 0.021 Uiso 1 1 calc R . . C10 C 0.19949(17) 1.21839(15) 0.74188(15) 0.0183(4) Uani 1 1 d . . . H10 H 0.2868 1.2211 0.7389 0.022 Uiso 1 1 calc R . . C12 C 0.14843(17) 1.31370(15) 0.78910(14) 0.0172(4) Uani 1 1 d . . . N14 N 0.38406(16) 1.62056(13) 0.90268(13) 0.0261(4) Uani 1 1 d . . . C19 C 0.17463(17) 1.01646(15) 0.64372(14) 0.0168(4) Uani 1 1 d . . . C21 C -0.04896(17) 1.21888(15) 0.75447(14) 0.0171(4) Uani 1 1 d . . . C22 C 0.27886(18) 0.82582(15) 0.53321(15) 0.0187(4) Uani 1 1 d . . . C25 C 0.18132(18) 1.51312(15) 0.84678(15) 0.0208(4) Uani 1 1 d . . . H25 H 0.0946 1.5104 0.8336 0.025 Uiso 1 1 calc R . . C28 C 0.34771(17) 0.91537(15) 0.61734(15) 0.0198(4) Uani 1 1 d . . . H28 H 0.4301 0.9120 0.6378 0.024 Uiso 1 1 calc R . . N29 N -0.44029(15) 1.24024(14) 0.77133(14) 0.0263(4) Uani 1 1 d . . . C31 C -0.18427(17) 1.22370(15) 0.76233(15) 0.0172(4) Uani 1 1 d . . . C32 C 0.22918(17) 1.42058(15) 0.83147(14) 0.0178(4) Uani 1 1 d . . . C33 C 0.12290(17) 1.11889(15) 0.69889(14) 0.0173(4) Uani 1 1 d . . . C34 C 0.15667(18) 0.83100(15) 0.50589(15) 0.0205(4) Uani 1 1 d . . . H34 H 0.1079 0.7699 0.4499 0.025 Uiso 1 1 calc R . . C35 C -0.27355(17) 1.14147(16) 0.68948(16) 0.0218(4) Uani 1 1 d . . . H35 H -0.2495 1.0780 0.6355 0.026 Uiso 1 1 calc R . . C38 C 0.35709(18) 1.43142(16) 0.85435(16) 0.0242(5) Uani 1 1 d . . . H38 H 0.3944 1.3709 0.8463 0.029 Uiso 1 1 calc R . . C41 C 0.26101(19) 1.60963(16) 0.88144(16) 0.0235(5) Uani 1 1 d . . . H41 H 0.2262 1.6716 0.8906 0.028 Uiso 1 1 calc R . . C43 C 0.29647(17) 1.00892(15) 0.67106(15) 0.0191(4) Uani 1 1 d . . . H43 H 0.3448 1.0695 0.7278 0.023 Uiso 1 1 calc R . . C46 C 0.10657(18) 0.92594(15) 0.56096(15) 0.0197(4) Uani 1 1 d . . . H46 H 0.0236 0.9289 0.5414 0.024 Uiso 1 1 calc R . . C49 C -0.39815(18) 1.15376(17) 0.69703(17) 0.0247(5) Uani 1 1 d . . . H49 H -0.4575 1.0972 0.6463 0.030 Uiso 1 1 calc R . . C50 C -0.22698(18) 1.31358(16) 0.84028(15) 0.0213(4) Uani 1 1 d . . . H50 H -0.1698 1.3712 0.8922 0.026 Uiso 1 1 calc R . . C51 C -0.35345(18) 1.31813(16) 0.84137(16) 0.0246(5) Uani 1 1 d . . . H51 H -0.3803 1.3803 0.8951 0.030 Uiso 1 1 calc R . . C52 C 0.3567(2) 0.56441(16) 0.33981(16) 0.0291(5) Uani 1 1 d . . . H52A H 0.4355 0.6024 0.3335 0.035 Uiso 1 1 calc R . . H52B H 0.3184 0.5131 0.2685 0.035 Uiso 1 1 calc R . . C53 C 0.3860(2) 0.50116(17) 0.39452(18) 0.0327(5) Uani 1 1 d . . . H53A H 0.3073 0.4688 0.4074 0.039 Uiso 1 1 calc R . . H53B H 0.4329 0.5509 0.4629 0.039 Uiso 1 1 calc R . . C54 C 0.2711(2) 0.64612(15) 0.39296(16) 0.0266(5) Uani 1 1 d . . . H54A H 0.2384 0.6698 0.3443 0.032 Uiso 1 1 calc R . . H54B H 0.2000 0.6131 0.4140 0.032 Uiso 1 1 calc R . . C56 C 0.42881(19) 1.53087(16) 0.88880(17) 0.0280(5) Uani 1 1 d . . . H56 H 0.5157 1.5362 0.9037 0.034 Uiso 1 1 calc R . . C57 C 0.4616(3) 0.41186(18) 0.33197(19) 0.0440(7) Uani 1 1 d . . . H57A H 0.4214 0.3684 0.2608 0.066 Uiso 1 1 calc R . . H57B H 0.4667 0.3657 0.3648 0.066 Uiso 1 1 calc R . . H57C H 0.5455 0.4440 0.3301 0.066 Uiso 1 1 calc R . . O2 O 0.82310(12) 0.51147(10) 0.41648(11) 0.0242(3) Uani 1 1 d . . . N4 N 1.11124(14) -0.07566(12) 0.08235(12) 0.0174(4) Uani 1 1 d . . . C5 C 0.93722(17) 0.02210(15) 0.13149(14) 0.0170(4) Uani 1 1 d . . . H5 H 0.8496 0.0201 0.1287 0.020 Uiso 1 1 calc R . . C6 C 0.95707(18) -0.27560(15) -0.00016(15) 0.0191(4) Uani 1 1 d . . . H6 H 1.0439 -0.2735 0.0113 0.023 Uiso 1 1 calc R . . C8 C 0.98804(17) -0.07360(15) 0.08275(14) 0.0163(4) Uani 1 1 d . . . C9 C 1.14294(17) 0.11770(15) 0.18406(14) 0.0181(4) Uani 1 1 d . . . H9 H 1.1997 0.1828 0.2199 0.022 Uiso 1 1 calc R . . C11 C 0.87448(18) 0.42003(15) 0.35745(15) 0.0189(4) Uani 1 1 d . . . N13 N 1.57906(15) -0.00052(14) 0.11697(13) 0.0230(4) Uani 1 1 d . . . C15 C 1.01526(17) 0.12084(15) 0.18440(14) 0.0166(4) Uani 1 1 d . . . C16 C 0.90743(17) -0.18051(14) 0.02950(14) 0.0160(4) Uani 1 1 d . . . C17 C 1.32252(17) 0.01362(15) 0.12755(14) 0.0164(4) Uani 1 1 d . . . C18 C 0.80388(18) 0.32289(15) 0.33739(15) 0.0208(4) Uani 1 1 d . . . H18 H 0.7247 0.3226 0.3628 0.025 Uiso 1 1 calc R . . C20 C 0.96548(17) 0.22443(14) 0.24141(14) 0.0160(4) Uani 1 1 d . . . C23 C 1.18719(16) 0.01934(15) 0.13130(14) 0.0163(4) Uani 1 1 d . . . N24 N 0.75576(15) -0.38439(13) -0.06744(13) 0.0243(4) Uani 1 1 d . . . C26 C 1.03315(17) 0.32248(15) 0.26035(15) 0.0185(4) Uani 1 1 d . . . H26 H 1.1113 0.3228 0.2333 0.022 Uiso 1 1 calc R . . C27 C 0.77918(17) -0.19064(15) 0.00809(15) 0.0212(4) Uani 1 1 d . . . H27 H 0.7403 -0.1283 0.0262 0.025 Uiso 1 1 calc R . . C30 C 1.53476(18) 0.09166(16) 0.14074(15) 0.0232(5) Uani 1 1 d . . . H30 H 1.5923 0.1534 0.1539 0.028 Uiso 1 1 calc R . . C36 C 1.41002(17) 0.10266(16) 0.14728(15) 0.0206(4) Uani 1 1 d . . . H36 H 1.3842 0.1705 0.1651 0.025 Uiso 1 1 calc R . . C37 C 1.36797(18) -0.08293(16) 0.10175(15) 0.0203(4) Uani 1 1 d . . . H37 H 1.3125 -0.1463 0.0869 0.024 Uiso 1 1 calc R . . C39 C 0.87869(19) -0.37355(16) -0.04667(16) 0.0231(5) Uani 1 1 d . . . H39 H 0.9147 -0.4373 -0.0650 0.028 Uiso 1 1 calc R . . C40 C 1.49408(18) -0.08585(16) 0.09799(16) 0.0234(5) Uani 1 1 d . . . H40 H 1.5227 -0.1525 0.0809 0.028 Uiso 1 1 calc R . . C42 C 0.84916(17) 0.22693(15) 0.28053(15) 0.0193(4) Uani 1 1 d . . . H42 H 0.8005 0.1610 0.2676 0.023 Uiso 1 1 calc R . . C44 C 0.89965(18) 0.61357(15) 0.44952(17) 0.0242(5) Uani 1 1 d . . . H44A H 0.9205 0.6225 0.3883 0.029 Uiso 1 1 calc R . . H44B H 0.9780 0.6171 0.4881 0.029 Uiso 1 1 calc R . . C45 C 0.98908(18) 0.41969(15) 0.31787(15) 0.0209(4) Uani 1 1 d . . . H45 H 1.0369 0.4857 0.3302 0.025 Uiso 1 1 calc R . . C47 C 0.70960(19) -0.29217(16) -0.03973(16) 0.0247(5) Uani 1 1 d . . . H47 H 0.6227 -0.2970 -0.0540 0.030 Uiso 1 1 calc R . . C48 C 0.82831(19) 0.70187(16) 0.51905(17) 0.0269(5) Uani 1 1 d . . . H48A H 0.8838 0.7719 0.5485 0.032 Uiso 1 1 calc R . . H48B H 0.8050 0.6893 0.5778 0.032 Uiso 1 1 calc R . . C55 C 0.7117(2) 0.71016(19) 0.46540(18) 0.0351(6) Uani 1 1 d . . . H55A H 0.7305 0.7046 0.3973 0.042 Uiso 1 1 calc R . . H55B H 0.6475 0.6484 0.4518 0.042 Uiso 1 1 calc R . . C58 C 0.6600(2) 0.8136(2) 0.5277(2) 0.0577(9) Uani 1 1 d . . . H58A H 0.6431 0.8208 0.5960 0.087 Uiso 1 1 calc R . . H58B H 0.5826 0.8124 0.4907 0.087 Uiso 1 1 calc R . . H58C H 0.7204 0.8750 0.5369 0.087 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 O1 0.0221(7) 0.0156(7) 0.0261(8) 0.0051(6) 0.0032(6) 0.0041(6) N3 0.0146(8) 0.0185(8) 0.0207(9) 0.0092(7) 0.0016(7) 0.0008(7) C7 0.0148(10) 0.0171(10) 0.0208(10) 0.0100(8) 0.0028(8) 0.0006(8) C10 0.0130(9) 0.0198(10) 0.0231(10) 0.0108(8) 0.0031(8) 0.0024(8) C12 0.0156(10) 0.0173(10) 0.0200(10) 0.0099(8) 0.0030(8) 0.0019(8) N14 0.0223(9) 0.0193(9) 0.0319(10) 0.0088(8) 0.0044(8) 0.0005(7) C19 0.0153(10) 0.0169(10) 0.0201(10) 0.0098(8) 0.0053(8) 0.0035(8) C21 0.0136(9) 0.0200(10) 0.0185(10) 0.0098(8) 0.0032(7) 0.0018(8) C22 0.0193(10) 0.0172(10) 0.0211(10) 0.0096(8) 0.0063(8) 0.0041(8) C25 0.0171(10) 0.0229(11) 0.0225(11) 0.0105(9) 0.0031(8) 0.0042(8) C28 0.0138(10) 0.0199(10) 0.0251(11) 0.0100(9) 0.0028(8) 0.0026(8) N29 0.0192(9) 0.0281(10) 0.0357(11) 0.0175(9) 0.0077(8) 0.0067(8) C31 0.0146(9) 0.0178(10) 0.0232(10) 0.0128(8) 0.0050(8) 0.0029(8) C32 0.0166(10) 0.0170(10) 0.0182(10) 0.0071(8) 0.0041(8) 0.0014(8) C33 0.0184(10) 0.0175(10) 0.0168(10) 0.0085(8) 0.0035(8) 0.0034(8) C34 0.0201(10) 0.0183(10) 0.0203(10) 0.0080(8) -0.0009(8) -0.0010(8) C35 0.0170(10) 0.0192(10) 0.0286(11) 0.0109(9) 0.0046(8) 0.0024(8) C38 0.0179(10) 0.0177(10) 0.0360(12) 0.0117(9) 0.0037(9) 0.0038(8) C41 0.0238(11) 0.0172(10) 0.0282(11) 0.0090(9) 0.0043(9) 0.0052(8) C43 0.0156(10) 0.0179(10) 0.0206(10) 0.0071(8) 0.0018(8) 0.0001(8) C46 0.0153(10) 0.0209(10) 0.0230(11) 0.0107(9) 0.0008(8) 0.0025(8) C49 0.0163(10) 0.0245(11) 0.0321(12) 0.0134(10) 0.0017(9) -0.0008(9) C50 0.0196(10) 0.0219(10) 0.0228(11) 0.0113(9) 0.0025(8) 0.0022(8) C51 0.0226(11) 0.0234(11) 0.0298(12) 0.0128(9) 0.0088(9) 0.0086(9) C52 0.0413(13) 0.0198(11) 0.0221(11) 0.0054(9) 0.0018(9) 0.0102(10) C53 0.0392(14) 0.0266(12) 0.0335(13) 0.0148(10) 0.0029(10) 0.0074(10) C54 0.0334(12) 0.0163(10) 0.0226(11) 0.0037(9) -0.0057(9) 0.0029(9) C56 0.0166(10) 0.0233(11) 0.0392(13) 0.0109(10) 0.0036(9) 0.0028(9) C57 0.0651(18) 0.0271(13) 0.0349(14) 0.0084(11) -0.0023(12) 0.0197(12) O2 0.0224(7) 0.0137(7) 0.0319(8) 0.0066(6) 0.0072(6) 0.0039(6) N4 0.0154(8) 0.0165(8) 0.0201(8) 0.0087(7) 0.0024(6) 0.0015(7) C5 0.0138(9) 0.0169(10) 0.0208(10) 0.0094(8) 0.0030(8) 0.0022(8) C6 0.0140(9) 0.0209(10) 0.0222(10) 0.0099(8) 0.0031(8) 0.0032(8) C8 0.0140(9) 0.0177(10) 0.0172(10) 0.0089(8) 0.0012(7) 0.0004(8) C9 0.0166(10) 0.0148(10) 0.0202(10) 0.0069(8) 0.0008(8) -0.0009(8) C11 0.0200(10) 0.0158(10) 0.0210(10) 0.0084(8) 0.0008(8) 0.0047(8) N13 0.0154(9) 0.0276(10) 0.0263(9) 0.0129(8) 0.0031(7) 0.0034(7) C15 0.0167(10) 0.0172(10) 0.0168(10) 0.0087(8) 0.0032(7) 0.0030(8) C16 0.0168(10) 0.0144(10) 0.0159(9) 0.0068(8) 0.0027(7) 0.0006(8) C17 0.0132(9) 0.0181(10) 0.0160(10) 0.0070(8) 0.0022(7) 0.0010(8) C18 0.0162(10) 0.0203(10) 0.0254(11) 0.0103(9) 0.0046(8) 0.0027(8) C20 0.0148(9) 0.0154(10) 0.0167(10) 0.0070(8) 0.0002(7) 0.0016(8) C23 0.0125(9) 0.0182(10) 0.0187(10) 0.0096(8) 0.0010(7) 0.0005(8) N24 0.0231(10) 0.0185(9) 0.0270(10) 0.0081(8) 0.0016(7) -0.0007(7) C26 0.0133(9) 0.0184(10) 0.0231(10) 0.0093(8) 0.0025(8) 0.0024(8) C27 0.0160(10) 0.0174(10) 0.0284(11) 0.0095(9) 0.0015(8) 0.0024(8) C30 0.0169(10) 0.0228(11) 0.0255(11) 0.0094(9) -0.0016(8) -0.0029(8) C36 0.0157(10) 0.0176(10) 0.0278(11) 0.0102(9) 0.0015(8) 0.0022(8) C37 0.0175(10) 0.0203(10) 0.0257(11) 0.0127(9) 0.0062(8) 0.0041(8) C39 0.0237(11) 0.0167(10) 0.0279(11) 0.0096(9) 0.0043(9) 0.0041(8) C40 0.0199(10) 0.0229(11) 0.0294(11) 0.0132(9) 0.0060(9) 0.0064(9) C42 0.0167(10) 0.0183(10) 0.0231(10) 0.0104(9) 0.0026(8) 0.0007(8) C44 0.0205(11) 0.0163(10) 0.0318(12) 0.0087(9) 0.0017(9) 0.0011(8) C45 0.0180(10) 0.0153(10) 0.0278(11) 0.0099(9) 0.0014(8) -0.0013(8) C47 0.0143(10) 0.0229(11) 0.0321(12) 0.0102(9) 0.0004(8) -0.0015(8) C48 0.0260(11) 0.0189(11) 0.0304(12) 0.0070(9) 0.0047(9) 0.0039(9) C55 0.0376(13) 0.0361(13) 0.0359(13) 0.0179(11) 0.0103(11) 0.0167(11) C58 0.0369(16) 0.0373(15) 0.086(2) 0.0159(15) 0.0077(15) 0.0187(12) _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 O1 C22 1.366(2) . ? O1 C54 1.438(2) . ? N3 C21 1.349(2) . ? N3 C12 1.349(2) . ? C7 C21 1.389(3) . ? C7 C33 1.395(3) . ? C10 C12 1.390(3) . ? C10 C33 1.394(3) . ? C12 C32 1.493(3) . ? N14 C41 1.340(3) . ? N14 C56 1.342(3) . ? C19 C46 1.388(3) . ? C19 C43 1.404(3) . ? C19 C33 1.481(3) . ? C21 C31 1.488(3) . ? C22 C28 1.394(3) . ? C22 C34 1.397(3) . ? C25 C41 1.389(3) . ? C25 C32 1.389(3) . ? C28 C43 1.381(3) . ? N29 C51 1.341(3) . ? N29 C49 1.343(3) . ? C31 C50 1.395(3) . ? C31 C35 1.395(3) . ? C32 C38 1.396(3) . ? C34 C46 1.392(3) . ? C35 C49 1.389(3) . ? C38 C56 1.380(3) . ? C50 C51 1.386(3) . ? C52 C54 1.504(3) . ? C52 C53 1.505(3) . ? C53 C57 1.523(3) . ? O2 C11 1.373(2) . ? O2 C44 1.436(2) . ? N4 C8 1.345(2) . ? N4 C23 1.346(2) . ? C5 C8 1.395(3) . ? C5 C15 1.396(2) . ? C6 C39 1.387(3) . ? C6 C16 1.389(3) . ? C8 C16 1.489(2) . ? C9 C23 1.393(3) . ? C9 C15 1.396(3) . ? C11 C18 1.391(3) . ? C11 C45 1.391(3) . ? N13 C30 1.338(3) . ? N13 C40 1.344(3) . ? C15 C20 1.486(3) . ? C16 C27 1.397(3) . ? C17 C37 1.394(3) . ? C17 C36 1.395(3) . ? C17 C23 1.486(2) . ? C18 C42 1.380(3) . ? C20 C26 1.393(3) . ? C20 C42 1.403(3) . ? N24 C39 1.338(2) . ? N24 C47 1.339(3) . ? C26 C45 1.388(3) . ? C27 C47 1.380(3) . ? C30 C36 1.386(3) . ? C37 C40 1.381(3) . ? C44 C48 1.511(3) . ? C48 C55 1.516(3) . ? C55 C58 1.505(3) . ? 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 C22 O1 C54 117.27(15) . . ? C21 N3 C12 117.36(16) . . ? C21 C7 C33 119.69(17) . . ? C12 C10 C33 120.16(17) . . ? N3 C12 C10 122.58(17) . . ? N3 C12 C32 116.81(16) . . ? C10 C12 C32 120.51(17) . . ? C41 N14 C56 115.84(17) . . ? C46 C19 C43 117.59(17) . . ? C46 C19 C33 121.48(17) . . ? C43 C19 C33 120.88(17) . . ? N3 C21 C7 123.09(17) . . ? N3 C21 C31 115.75(16) . . ? C7 C21 C31 121.16(16) . . ? O1 C22 C28 116.18(16) . . ? O1 C22 C34 124.61(17) . . ? C28 C22 C34 119.21(17) . . ? C41 C25 C32 119.59(18) . . ? C43 C28 C22 120.19(18) . . ? C51 N29 C49 115.91(17) . . ? C50 C31 C35 117.12(17) . . ? C50 C31 C21 121.11(17) . . ? C35 C31 C21 121.70(17) . . ? C25 C32 C38 116.86(17) . . ? C25 C32 C12 121.66(17) . . ? C38 C32 C12 121.45(17) . . ? C10 C33 C7 117.04(17) . . ? C10 C33 C19 121.05(17) . . ? C7 C33 C19 121.89(16) . . ? C46 C34 C22 119.77(17) . . ? C49 C35 C31 119.05(18) . . ? C56 C38 C32 119.38(19) . . ? N14 C41 C25 123.94(19) . . ? C28 C43 C19 121.49(17) . . ? C19 C46 C34 121.72(18) . . ? N29 C49 C35 124.34(18) . . ? C51 C50 C31 119.50(18) . . ? N29 C51 C50 124.07(18) . . ? C54 C52 C53 114.66(19) . . ? C52 C53 C57 112.5(2) . . ? O1 C54 C52 109.55(17) . . ? N14 C56 C38 124.38(19) . . ? C11 O2 C44 117.19(15) . . ? C8 N4 C23 117.79(16) . . ? C8 C5 C15 119.89(17) . . ? C39 C6 C16 119.41(18) . . ? N4 C8 C5 122.73(16) . . ? N4 C8 C16 116.06(16) . . ? C5 C8 C16 121.21(16) . . ? C23 C9 C15 120.13(16) . . ? O2 C11 C18 115.74(17) . . ? O2 C11 C45 124.45(17) . . ? C18 C11 C45 119.81(17) . . ? C30 N13 C40 115.88(17) . . ? C5 C15 C9 116.89(17) . . ? C5 C15 C20 121.82(16) . . ? C9 C15 C20 121.27(16) . . ? C6 C16 C27 116.75(16) . . ? C6 C16 C8 120.96(17) . . ? C27 C16 C8 122.28(17) . . ? C37 C17 C36 116.58(17) . . ? C37 C17 C23 120.98(16) . . ? C36 C17 C23 122.43(17) . . ? C42 C18 C11 119.85(18) . . ? C26 C20 C42 117.59(17) . . ? C26 C20 C15 121.61(17) . . ? C42 C20 C15 120.78(16) . . ? N4 C23 C9 122.53(17) . . ? N4 C23 C17 116.08(16) . . ? C9 C23 C17 121.38(16) . . ? C39 N24 C47 115.41(16) . . ? C45 C26 C20 121.53(18) . . ? C47 C27 C16 119.27(18) . . ? N13 C30 C36 124.01(18) . . ? C30 C36 C17 119.69(18) . . ? C40 C37 C17 119.59(18) . . ? N24 C39 C6 124.45(19) . . ? N13 C40 C37 124.26(19) . . ? C18 C42 C20 121.51(18) . . ? O2 C44 C48 108.14(16) . . ? C26 C45 C11 119.68(18) . . ? N24 C47 C27 124.70(18) . . ? C44 C48 C55 114.67(17) . . ? C58 C55 C48 113.42(19) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.393 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.110