# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Martin R. Bryce' 'Andrei S. Batsanov' 'Nezire Saygili' _publ_contact_author_name 'Prof Martin R Bryce' _publ_contact_author_address ; Department of Chemistry University of Durham Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email M.R.BRYCE@DURHAM.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; 5-Pyrimidylboronic acid and 2-methoxy-5-pyrimidylboronic acid: new heteroarylpyrimidine derivatives via Suzuki cross-coupling reactions ; data_(2) _database_code_depnum_ccdc_archive 'CCDC 224163' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-pyrimidylboronic acid hemihydrate ; _chemical_name_common ? _chemical_melting_point '>320\% C' _chemical_formula_moiety 'C4 H5 B N2 O2,0.5(H2 O)' _chemical_formula_sum 'C4 H6 B N2 O2.5' _chemical_formula_weight 132.92 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 0.0000 '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' B B 0.0013 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 7.6474(7) _cell_length_b 21.062(5) _cell_length_c 3.6345(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 585.41(15) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 983 _cell_measurement_theta_min 10.23 _cell_measurement_theta_max 24.84 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8954 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker,2001), R(int)=0.065 before correction' _exptl_special_details ; The data collection nominally covered full sphere of reciprocal space, by a combination of 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan (20 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.85 cm. ; _diffrn_ambient_temperature 120(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 'SMART 6K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 7717 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 29.95 _reflns_number_total 1039 _reflns_number_gt 936 _reflns_threshold_expression I>2\s(I) _reflns_Friedel_coverage 0.63 _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SMART version 5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXTL version 6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL version 6.12 (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 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. ; _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^)+(0.0489P)^2^+0.1055P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'undeterminable, Friedel equivalents merged, all \Df" set to 0' _refine_ls_number_reflns 1039 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0835 _refine_ls_wR_factor_gt 0.0797 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.70949(15) 0.55594(5) 0.5385(4) 0.0222(3) Uani 1 1 d . . . H01 H 0.803(3) 0.5456(11) 0.442(8) 0.036(6) Uiso 1 1 d . . . O2 O 0.76768(14) 0.65984(5) 0.3262(4) 0.0193(3) Uani 1 1 d . . . H02 H 0.729(3) 0.6970(13) 0.299(9) 0.051(8) Uiso 1 1 d . . . B B 0.6608(2) 0.61697(8) 0.4938(5) 0.0164(3) Uani 1 1 d . . . N1 N 0.19394(17) 0.59901(6) 0.8793(4) 0.0178(3) Uani 1 1 d . . . C2 C 0.14192(19) 0.65963(7) 0.8640(5) 0.0173(3) Uani 1 1 d . . . H2 H 0.022(2) 0.6684(9) 0.949(6) 0.022(5) Uiso 1 1 d . . . N3 N 0.23821(17) 0.70878(6) 0.7491(4) 0.0179(3) Uani 1 1 d . . . C4 C 0.40150(19) 0.69514(7) 0.6350(5) 0.0167(3) Uani 1 1 d . . . H4 H 0.472(2) 0.7303(9) 0.557(6) 0.018(5) Uiso 1 1 d . . . C5 C 0.47090(19) 0.63419(7) 0.6352(5) 0.0147(3) Uani 1 1 d . . . C6 C 0.3577(2) 0.58728(7) 0.7663(5) 0.0169(3) Uani 1 1 d . . . H6 H 0.395(2) 0.5432(9) 0.773(6) 0.016(5) Uiso 1 1 d . . . O3 O 0.0000 0.5000 1.2315(5) 0.0175(3) Uani 1 2 d S . . H03 H 0.049(3) 0.5293(10) 1.110(8) 0.042(7) 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 O1 0.0184(5) 0.0150(5) 0.0331(7) 0.0026(5) 0.0096(5) 0.0035(4) O2 0.0148(5) 0.0150(5) 0.0282(6) 0.0022(5) 0.0044(5) 0.0002(4) B 0.0146(7) 0.0159(7) 0.0188(7) -0.0015(7) 0.0012(7) -0.0004(6) N1 0.0157(6) 0.0168(6) 0.0208(6) -0.0005(5) 0.0017(5) -0.0013(5) C2 0.0137(6) 0.0188(7) 0.0196(7) 0.0011(6) 0.0013(6) 0.0004(5) N3 0.0151(5) 0.0163(5) 0.0224(6) 0.0017(5) 0.0006(5) 0.0009(4) C4 0.0148(6) 0.0156(6) 0.0198(7) 0.0017(6) 0.0007(6) -0.0012(5) C5 0.0124(6) 0.0150(6) 0.0167(7) -0.0007(6) 0.0007(6) 0.0001(5) C6 0.0167(6) 0.0134(6) 0.0207(7) -0.0001(6) 0.0009(6) -0.0013(5) O3 0.0141(7) 0.0146(7) 0.0238(8) 0.000 0.000 -0.0019(6) _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 B 1.348(2) . ? O1 H01 0.82(2) . ? O2 B 1.362(2) . ? O2 H02 0.84(3) . ? B C5 1.583(2) . ? N1 C2 1.3385(19) . ? N1 C6 1.341(2) . ? C2 N3 1.3373(19) . ? C2 H2 0.99(2) . ? N3 C4 1.3468(19) . ? C4 C5 1.3890(19) . ? C4 H4 0.959(19) . ? C5 C6 1.3974(19) . ? C6 H6 0.971(18) . ? O3 H03 0.85(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 B O1 H01 116.1(17) . . ? B O2 H02 117.5(19) . . ? O1 B O2 121.37(15) . . ? O1 B C5 115.64(14) . . ? O2 B C5 122.96(14) . . ? C2 N1 C6 116.14(13) . . ? N3 C2 N1 126.00(14) . . ? N3 C2 H2 117.7(11) . . ? N1 C2 H2 116.3(11) . . ? C2 N3 C4 116.20(13) . . ? N3 C4 C5 123.46(14) . . ? N3 C4 H4 116.5(11) . . ? C5 C4 H4 120.0(11) . . ? C4 C5 C6 114.64(13) . . ? C4 C5 B 124.21(13) . . ? C6 C5 B 121.14(13) . . ? N1 C6 C5 123.55(13) . . ? N1 C6 H6 116.2(11) . . ? C5 C6 H6 120.3(12) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H01 O3 0.82(2) 1.94(2) 2.7512(14) 166(2) 1_654 O2 H02 N3 0.84(3) 1.99(3) 2.7896(18) 158(2) 4_566 O3 H03 N1 0.85(2) 2.02(2) 2.8612(16) 172(3) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 29.95 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.280 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.045 #=============================================END data_(18) _database_code_depnum_ccdc_archive 'CCDC 224164' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,6-bis(2-methoxy-3-pyridyl)pyrimidine ; _chemical_name_common ? _chemical_melting_point '115--116\% C' _chemical_formula_moiety 'C16 H14 N4 O2' _chemical_formula_sum 'C16 H14 N4 O2' _chemical_formula_weight 294.31 _chemical_absolute_configuration un 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.1245(11) _cell_length_b 3.7622(7) _cell_length_c 20.595(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.806(4) _cell_angle_gamma 90.00 _cell_volume 703.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 947 _cell_measurement_theta_min 10.2 _cell_measurement_theta_max 25.7 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The data collection nominally covered full sphere of reciprocal space, by a combination of 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan (15 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.85 cm. Without merging Friedel equivalents, 4095 unique reflections. ; _diffrn_ambient_temperature 120(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 'SMART 6K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 10016 _diffrn_reflns_av_R_equivalents 0.0694 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 29.99 _reflns_number_total 2337 _reflns_number_gt 1881 _reflns_threshold_expression I>2\s(I) _reflns_Friedel_coverage 0.75 _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SMART version 5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXTL version 6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL version 6.12 (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 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. ; _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^)+(0.0608P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'undeterminable, Friedel equivalents merged, all \Df" set to 0' _refine_ls_number_reflns 2337 _refine_ls_number_parameters 255 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1040 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.000 _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 0.68620(14) 0.8452(4) 0.28622(7) 0.0230(3) Uani 1 1 d . . . O2 O 0.48002(14) 1.2336(5) 0.13854(6) 0.0275(3) Uani 1 1 d . . . N1 N 0.15461(17) 1.1754(5) 0.26666(8) 0.0255(4) Uani 1 1 d . . . C2 C 0.1791(2) 1.0683(7) 0.32825(10) 0.0278(5) Uani 1 1 d . . . H2 H 0.090(2) 1.002(7) 0.3484(10) 0.020(5) Uiso 1 1 d . . . N3 N 0.30919(17) 1.0342(5) 0.36433(8) 0.0242(4) Uani 1 1 d . . . C4 C 0.42792(19) 1.1183(5) 0.33355(9) 0.0186(4) Uani 1 1 d . . . C5 C 0.41532(19) 1.2348(6) 0.26939(9) 0.0196(4) Uani 1 1 d . . . H5 H 0.498(2) 1.301(6) 0.2497(10) 0.015(5) Uiso 1 1 d . . . C6 C 0.27480(19) 1.2604(5) 0.23644(9) 0.0200(4) Uani 1 1 d . . . C7 C 0.8155(2) 0.7014(7) 0.26121(11) 0.0259(4) Uani 1 1 d . . . H71 H 0.782(3) 0.595(8) 0.2191(12) 0.029(6) Uiso 1 1 d . . . H72 H 0.884(2) 0.885(8) 0.2547(11) 0.024(6) Uiso 1 1 d . . . H73 H 0.867(3) 0.518(10) 0.2938(14) 0.054(9) Uiso 1 1 d . . . C8 C 0.5789(3) 1.2028(7) 0.08878(11) 0.0315(5) Uani 1 1 d . . . H81 H 0.667(3) 1.083(8) 0.1111(11) 0.034(7) Uiso 1 1 d . . . H82 H 0.536(2) 1.056(8) 0.0533(11) 0.026(6) Uiso 1 1 d . . . H83 H 0.601(3) 1.435(9) 0.0713(14) 0.050(9) Uiso 1 1 d . . . N11 N 0.83219(17) 0.9552(5) 0.38229(8) 0.0231(4) Uani 1 1 d . . . C12 C 0.7005(2) 0.9673(5) 0.34819(9) 0.0189(4) Uani 1 1 d . . . C13 C 0.57228(19) 1.0944(5) 0.37344(8) 0.0190(4) Uani 1 1 d . . . C14 C 0.5867(2) 1.2017(6) 0.43784(9) 0.0214(4) Uani 1 1 d . . . H14 H 0.500(2) 1.286(7) 0.4566(10) 0.025(6) Uiso 1 1 d . . . C15 C 0.7234(2) 1.1889(6) 0.47465(9) 0.0248(4) Uani 1 1 d . . . H15 H 0.730(2) 1.272(7) 0.5187(11) 0.026(6) Uiso 1 1 d . . . C16 C 0.8408(2) 1.0669(6) 0.44450(10) 0.0263(4) Uani 1 1 d . . . H16 H 0.941(2) 1.048(7) 0.4683(10) 0.026(6) Uiso 1 1 d . . . N21 N 0.3178(2) 1.4933(5) 0.06008(8) 0.0271(4) Uani 1 1 d . . . C22 C 0.3464(2) 1.3768(6) 0.12083(9) 0.0231(4) Uani 1 1 d . . . C23 C 0.2446(2) 1.3893(5) 0.16836(9) 0.0212(4) Uani 1 1 d . . . C24 C 0.1065(2) 1.5269(6) 0.14756(10) 0.0254(4) Uani 1 1 d . . . H24 H 0.039(3) 1.545(8) 0.1796(11) 0.031(6) Uiso 1 1 d . . . C25 C 0.0747(2) 1.6496(6) 0.08420(10) 0.0294(5) Uani 1 1 d . . . H25 H -0.016(3) 1.752(9) 0.0707(12) 0.040(7) Uiso 1 1 d . . . C26 C 0.1835(2) 1.6308(6) 0.04291(10) 0.0287(5) Uani 1 1 d . . . H26 H 0.173(2) 1.713(8) -0.0018(11) 0.031(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 O1 0.0164(6) 0.0323(7) 0.0206(7) -0.0057(6) 0.0040(5) 0.0007(6) O2 0.0236(7) 0.0394(9) 0.0200(7) 0.0011(7) 0.0054(5) 0.0044(7) N1 0.0180(7) 0.0350(10) 0.0238(8) 0.0007(8) 0.0036(6) -0.0003(7) C2 0.0182(9) 0.0410(12) 0.0247(10) 0.0008(9) 0.0050(7) -0.0019(9) N3 0.0179(8) 0.0336(9) 0.0216(8) 0.0028(7) 0.0054(6) -0.0006(7) C4 0.0160(8) 0.0214(9) 0.0185(8) -0.0028(7) 0.0026(6) 0.0005(7) C5 0.0165(8) 0.0233(9) 0.0195(8) -0.0010(8) 0.0036(6) -0.0024(7) C6 0.0187(8) 0.0228(9) 0.0187(9) -0.0034(8) 0.0024(6) -0.0007(8) C7 0.0197(9) 0.0313(10) 0.0279(10) -0.0080(9) 0.0088(7) -0.0015(9) C8 0.0317(11) 0.0383(12) 0.0263(11) 0.0012(10) 0.0117(8) 0.0053(11) N11 0.0180(7) 0.0264(9) 0.0246(8) 0.0008(7) 0.0005(6) -0.0016(7) C12 0.0184(8) 0.0193(9) 0.0195(9) -0.0005(7) 0.0035(6) -0.0016(7) C13 0.0172(8) 0.0214(9) 0.0188(9) 0.0007(7) 0.0034(6) -0.0013(7) C14 0.0230(9) 0.0235(9) 0.0182(8) 0.0005(8) 0.0045(7) -0.0007(8) C15 0.0297(10) 0.0268(10) 0.0174(9) -0.0002(8) 0.0000(7) -0.0026(9) C16 0.0235(9) 0.0309(11) 0.0231(10) 0.0013(8) -0.0040(7) -0.0030(9) N21 0.0321(9) 0.0280(9) 0.0208(8) 0.0010(7) 0.0014(7) -0.0037(8) C22 0.0229(9) 0.0247(9) 0.0213(9) -0.0011(8) 0.0000(7) -0.0009(8) C23 0.0222(9) 0.0206(9) 0.0204(9) -0.0027(8) -0.0002(7) -0.0023(8) C24 0.0236(9) 0.0278(11) 0.0242(10) -0.0021(8) -0.0001(7) 0.0008(8) C25 0.0284(10) 0.0280(11) 0.0296(11) 0.0001(9) -0.0085(8) 0.0007(9) C26 0.0339(10) 0.0276(10) 0.0229(10) 0.0033(8) -0.0057(8) -0.0016(9) _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 C12 1.350(2) . ? O1 C7 1.440(2) . ? O2 C22 1.349(2) . ? O2 C8 1.437(2) . ? N1 C2 1.328(3) . ? N1 C6 1.353(2) . ? C2 N3 1.341(2) . ? N3 C4 1.347(2) . ? C4 C5 1.386(3) . ? C4 C13 1.483(2) . ? C5 C6 1.392(2) . ? C6 C23 1.483(3) . ? N11 C12 1.329(2) . ? N11 C16 1.343(3) . ? C12 C13 1.411(2) . ? C13 C14 1.380(3) . ? C14 C15 1.393(3) . ? C15 C16 1.371(3) . ? N21 C22 1.327(3) . ? N21 C26 1.344(3) . ? C22 C23 1.417(3) . ? C23 C24 1.389(3) . ? C24 C25 1.387(3) . ? C25 C26 1.373(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 C12 O1 C7 117.48(15) . . ? C22 O2 C8 117.04(16) . . ? C2 N1 C6 116.44(16) . . ? N1 C2 N3 127.72(18) . . ? C2 N3 C4 115.20(17) . . ? N3 C4 C5 122.00(16) . . ? N3 C4 C13 115.89(16) . . ? C5 C4 C13 122.06(15) . . ? C4 C5 C6 118.04(16) . . ? N1 C6 C5 120.60(16) . . ? N1 C6 C23 115.49(16) . . ? C5 C6 C23 123.89(16) . . ? C12 N11 C16 117.13(17) . . ? N11 C12 O1 118.92(16) . . ? N11 C12 C13 123.75(17) . . ? O1 C12 C13 117.31(16) . . ? C14 C13 C12 116.82(16) . . ? C14 C13 C4 120.52(16) . . ? C12 C13 C4 122.66(16) . . ? C13 C14 C15 120.41(17) . . ? C16 C15 C14 117.57(17) . . ? N11 C16 C15 124.30(18) . . ? C22 N21 C26 117.59(17) . . ? N21 C22 O2 118.29(17) . . ? N21 C22 C23 124.04(18) . . ? O2 C22 C23 117.67(17) . . ? C24 C23 C22 115.91(18) . . ? C24 C23 C6 119.33(17) . . ? C22 C23 C6 124.75(17) . . ? C25 C24 C23 120.77(19) . . ? C26 C25 C24 118.0(2) . . ? N21 C26 C25 123.7(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.236 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.048 #=============================================END