# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Roberto Quesada' _publ_contact_author_email rquesada@ubu.es loop_ _publ_author_name 'Paulina Iglesias Hernandez' 'Daniel Moreno' 'A.Araujo Javier' 'Toms Torroba' 'Ricardo Perez-Tomas' ; R.Quesada ; data_1 _database_code_depnum_ccdc_archive 'CCDC 804441' #TrackingRef 'web_deposit_cif_file_0_RobertoQuesada_1292092843.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H16 N3 O, H2 O, Cl' _chemical_formula_sum 'C12 H18 Cl N3 O2' _chemical_formula_weight 271.74 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.739(5) _cell_length_b 7.0220(18) _cell_length_c 21.543(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.563(4) _cell_angle_gamma 90.00 _cell_volume 2830.8(13) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3838 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 22.69 _exptl_crystal_description prism _exptl_crystal_colour YELLOW _exptl_crystal_size_max 1.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.730966 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (SHELDRICK, 2001' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12247 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2491 _reflns_number_gt 2188 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0578P)^2^+2.4372P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2491 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1204 _refine_ls_wR_factor_gt 0.1157 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 Cl1 Cl 0.18089(3) 0.44479(10) 0.15424(3) 0.0681(2) Uani 1 1 d . . . N1 N 0.11974(9) 0.6315(3) -0.12208(8) 0.0537(5) Uani 1 1 d . . . H1B H 0.1461 0.6610 -0.1456 0.064 Uiso 1 1 calc R . . N2 N 0.24338(8) 0.4698(2) 0.03537(7) 0.0429(4) Uani 1 1 d . . . H2B H 0.2182 0.4562 0.0611 0.051 Uiso 1 1 calc R . . N3 N 0.34162(10) 0.3264(3) 0.16284(8) 0.0521(4) Uani 1 1 d . . . O1 O 0.40241(7) 0.4614(2) -0.00409(7) 0.0602(4) Uani 1 1 d . . . O2 O 0.29324(14) 0.7851(4) 0.20288(11) 0.0876(6) Uani 1 1 d . . . C1 C 0.04777(12) 0.6452(4) -0.14100(12) 0.0692(7) Uani 1 1 d . . . H1 H 0.0188 0.6892 -0.1815 0.083 Uiso 1 1 calc R . . C2 C 0.02481(13) 0.5849(4) -0.09194(13) 0.0740(7) Uani 1 1 d . . . H2 H -0.0225 0.5790 -0.0926 0.089 Uiso 1 1 calc R . . C3 C 0.08478(12) 0.5326(4) -0.03988(12) 0.0612(6) Uani 1 1 d . . . H3 H 0.0849 0.4858 0.0006 0.073 Uiso 1 1 calc R . . C4 C 0.14379(11) 0.5634(3) -0.05976(10) 0.0457(5) Uani 1 1 d . . . C5 C 0.21793(10) 0.5259(3) -0.02758(9) 0.0421(4) Uani 1 1 d . . . C6 C 0.27445(10) 0.5336(3) -0.05335(9) 0.0450(5) Uani 1 1 d . . . H6 H 0.2717 0.5684 -0.0957 0.054 Uiso 1 1 calc R . . C7 C 0.33512(10) 0.4795(3) -0.00376(10) 0.0449(5) Uani 1 1 d . . . C8 C 0.31630(10) 0.4375(3) 0.05256(9) 0.0424(4) Uani 1 1 d . . . C9 C 0.41349(13) 0.5145(4) -0.06428(12) 0.0707(7) Uani 1 1 d . . . H9A H 0.3841 0.4370 -0.0992 0.106 Uiso 1 1 calc R . . H9B H 0.4628 0.4962 -0.0606 0.106 Uiso 1 1 calc R . . H9C H 0.4010 0.6461 -0.0734 0.106 Uiso 1 1 calc R . . C10 C 0.36005(10) 0.3700(3) 0.11156(9) 0.0460(5) Uani 1 1 d . . . H10 H 0.4080 0.3536 0.1154 0.055 Uiso 1 1 calc R . . C11 C 0.39047(12) 0.2511(4) 0.22375(10) 0.0631(6) Uani 1 1 d . . . H11A H 0.4339 0.2082 0.2161 0.076 Uiso 1 1 calc R . . H11B H 0.3686 0.1416 0.2372 0.076 Uiso 1 1 calc R . . C12 C 0.40905(17) 0.3925(5) 0.27690(13) 0.0995(11) Uani 1 1 d . . . H12A H 0.4325 0.4990 0.2646 0.149 Uiso 1 1 calc R . . H12B H 0.4405 0.3356 0.3160 0.149 Uiso 1 1 calc R . . H12C H 0.3663 0.4352 0.2848 0.149 Uiso 1 1 calc R . . H13 H 0.2631(17) 0.696(5) 0.1964(16) 0.095(11) Uiso 1 1 d . . . H14 H 0.3012(19) 0.807(6) 0.243(2) 0.125(14) Uiso 1 1 d . . . H15 H 0.2957(13) 0.349(3) 0.1613(11) 0.060(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 Cl1 0.0530(3) 0.1051(5) 0.0503(3) -0.0011(3) 0.0220(3) 0.0025(3) N1 0.0500(10) 0.0628(11) 0.0447(9) -0.0002(8) 0.0100(8) 0.0071(8) N2 0.0435(9) 0.0498(9) 0.0366(8) -0.0027(7) 0.0147(7) 0.0013(7) N3 0.0463(10) 0.0701(12) 0.0377(9) -0.0026(8) 0.0103(7) 0.0044(9) O1 0.0414(8) 0.0888(11) 0.0530(9) 0.0066(8) 0.0188(7) 0.0010(7) O2 0.1143(17) 0.0986(16) 0.0596(12) -0.0046(11) 0.0413(11) -0.0247(14) C1 0.0534(13) 0.0824(17) 0.0593(14) -0.0024(12) 0.0003(11) 0.0187(12) C2 0.0439(12) 0.097(2) 0.0809(18) -0.0071(15) 0.0202(12) 0.0130(12) C3 0.0500(12) 0.0761(16) 0.0609(14) 0.0007(11) 0.0225(11) 0.0094(11) C4 0.0469(11) 0.0457(11) 0.0442(10) -0.0056(8) 0.0141(9) 0.0041(9) C5 0.0440(10) 0.0398(10) 0.0412(10) -0.0049(8) 0.0119(8) 0.0004(8) C6 0.0477(11) 0.0498(11) 0.0391(10) 0.0003(8) 0.0158(9) -0.0018(9) C7 0.0410(10) 0.0486(11) 0.0460(11) -0.0046(9) 0.0148(8) -0.0044(8) C8 0.0402(10) 0.0457(11) 0.0398(10) -0.0048(8) 0.0105(8) -0.0009(8) C9 0.0522(13) 0.104(2) 0.0624(14) 0.0068(14) 0.0278(11) -0.0006(13) C10 0.0412(10) 0.0516(12) 0.0434(11) -0.0088(9) 0.0109(8) -0.0010(9) C11 0.0592(13) 0.0812(16) 0.0433(12) 0.0054(11) 0.0085(10) 0.0021(12) C12 0.092(2) 0.141(3) 0.0500(15) -0.0200(17) -0.0002(14) 0.023(2) _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 N1 C1 1.351(3) . ? N1 C4 1.360(3) . ? N1 H1B 0.8600 . ? N2 C5 1.346(2) . ? N2 C8 1.386(2) . ? N2 H2B 0.8600 . ? N3 C10 1.305(3) . ? N3 C11 1.458(3) . ? N3 H15 0.91(2) . ? O1 C7 1.337(2) . ? O1 C9 1.431(3) . ? O2 H13 0.84(3) . ? O2 H14 0.84(4) . ? C1 C2 1.344(4) . ? C1 H1 0.9300 . ? C2 C3 1.396(3) . ? C2 H2 0.9300 . ? C3 C4 1.380(3) . ? C3 H3 0.9300 . ? C4 C5 1.430(3) . ? C5 C6 1.397(3) . ? C6 C7 1.380(3) . ? C6 H6 0.9300 . ? C7 C8 1.409(3) . ? C8 C10 1.374(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10 0.9300 . ? C11 C12 1.471(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 C1 N1 C4 109.02(19) . . ? C1 N1 H1B 125.5 . . ? C4 N1 H1B 125.5 . . ? C5 N2 C8 109.87(16) . . ? C5 N2 H2B 125.1 . . ? C8 N2 H2B 125.1 . . ? C10 N3 C11 124.35(19) . . ? C10 N3 H15 118.1(15) . . ? C11 N3 H15 117.5(15) . . ? C7 O1 C9 114.75(16) . . ? H13 O2 H14 101(3) . . ? C2 C1 N1 109.0(2) . . ? C2 C1 H1 125.5 . . ? N1 C1 H1 125.5 . . ? C1 C2 C3 107.6(2) . . ? C1 C2 H2 126.2 . . ? C3 C2 H2 126.2 . . ? C4 C3 C2 107.0(2) . . ? C4 C3 H3 126.5 . . ? C2 C3 H3 126.5 . . ? N1 C4 C3 107.31(19) . . ? N1 C4 C5 121.65(18) . . ? C3 C4 C5 130.9(2) . . ? N2 C5 C6 108.81(17) . . ? N2 C5 C4 122.56(18) . . ? C6 C5 C4 128.60(18) . . ? C7 C6 C5 106.73(17) . . ? C7 C6 H6 126.6 . . ? C5 C6 H6 126.6 . . ? O1 C7 C6 129.86(18) . . ? O1 C7 C8 121.31(18) . . ? C6 C7 C8 108.82(17) . . ? C10 C8 N2 126.67(18) . . ? C10 C8 C7 127.50(18) . . ? N2 C8 C7 105.77(16) . . ? O1 C9 H9A 109.5 . . ? O1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 C8 126.99(19) . . ? N3 C10 H10 116.5 . . ? C8 C10 H10 116.5 . . ? N3 C11 C12 112.7(2) . . ? N3 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? N3 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 -0.6(3) . . . . ? N1 C1 C2 C3 0.5(3) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C1 N1 C4 C3 0.5(2) . . . . ? C1 N1 C4 C5 177.23(19) . . . . ? C2 C3 C4 N1 -0.2(3) . . . . ? C2 C3 C4 C5 -176.5(2) . . . . ? C8 N2 C5 C6 -0.6(2) . . . . ? C8 N2 C5 C4 177.78(17) . . . . ? N1 C4 C5 N2 175.74(18) . . . . ? C3 C4 C5 N2 -8.4(3) . . . . ? N1 C4 C5 C6 -6.2(3) . . . . ? C3 C4 C5 C6 169.6(2) . . . . ? N2 C5 C6 C7 0.2(2) . . . . ? C4 C5 C6 C7 -178.05(19) . . . . ? C9 O1 C7 C6 3.1(3) . . . . ? C9 O1 C7 C8 -178.3(2) . . . . ? C5 C6 C7 O1 179.0(2) . . . . ? C5 C6 C7 C8 0.3(2) . . . . ? C5 N2 C8 C10 -176.57(19) . . . . ? C5 N2 C8 C7 0.7(2) . . . . ? O1 C7 C8 C10 -2.2(3) . . . . ? C6 C7 C8 C10 176.67(19) . . . . ? O1 C7 C8 N2 -179.44(17) . . . . ? C6 C7 C8 N2 -0.6(2) . . . . ? C11 N3 C10 C8 178.5(2) . . . . ? N2 C8 C10 N3 -1.2(3) . . . . ? C7 C8 C10 N3 -177.9(2) . . . . ? C10 N3 C11 C12 106.5(3) . . . . ? 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 N3 H15 Cl1 0.91(2) 2.32(2) 3.228(2) 173(2) . O2 H14 Cl1 0.84(4) 2.34(4) 3.161(2) 166(4) 4 O2 H13 Cl1 0.84(3) 2.37(3) 3.201(3) 167(3) . N2 H2B Cl1 0.86 2.35 3.1815(17) 163.2 . N1 H1B O2 0.86 2.01 2.868(3) 176.7 7_565 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.231 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.038 # Attachment 'web_deposit_cif_file_1_RobertoQuesada_1292092843.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 804442' #TrackingRef 'web_deposit_cif_file_1_RobertoQuesada_1292092843.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H24 N3 O, H2 O, Cl' _chemical_formula_sum 'C20 H26 Cl N3 O2' _chemical_formula_weight 375.89 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' Cl Cl 0.1484 0.1585 '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)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.720(5) _cell_length_b 6.994(5) _cell_length_c 21.180(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 108.909(5) _cell_angle_gamma 90.000(5) _cell_volume 2062.8(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4499 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 21.71 _exptl_crystal_description PLATE _exptl_crystal_colour YELLOW _exptl_crystal_size_max 1.10 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.203 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8490 _exptl_absorpt_correction_T_max 0.9800 _exptl_absorpt_process_details 'SADABS (SHELDRICK, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 19322 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3630 _reflns_number_gt 2871 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1091P)^2^+0.6657P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3630 _refine_ls_number_parameters 247 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0610 _refine_ls_wR_factor_ref 0.1871 _refine_ls_wR_factor_gt 0.1769 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.001 _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 O2 O 0.2737(2) 0.5057(4) 0.67988(11) 0.0939(8) Uani 1 1 d D . . Cl1 Cl 0.11620(5) 0.19454(11) 0.67687(3) 0.0619(3) Uani 1 1 d . . . N1 N -0.1525(2) 0.3069(4) 0.56154(15) 0.0851(9) Uani 1 1 d . . . H1A H -0.1086 0.2715 0.5975 0.102 Uiso 1 1 calc R . . N2 N 0.02368(16) 0.2377(3) 0.51937(10) 0.0486(5) Uani 1 1 d . . . H2C H 0.0380 0.2284 0.5620 0.058 Uiso 1 1 calc R . . N3 N 0.22891(16) 0.1181(3) 0.57249(10) 0.0521(6) Uani 1 1 d . . . H3A H 0.1998 0.1401 0.6010 0.062 Uiso 1 1 calc R . . O1 O 0.07287(15) 0.2172(3) 0.36858(9) 0.0661(6) Uani 1 1 d . . . C1 C -0.2461(3) 0.3573(6) 0.55583(19) 0.0801(10) Uani 1 1 d . . . H1 H -0.2730 0.3592 0.5900 0.096 Uiso 1 1 calc R . . C2 C -0.2912(2) 0.4035(5) 0.49051(17) 0.0739(9) Uani 1 1 d . . . H2 H -0.3548 0.4422 0.4724 0.089 Uiso 1 1 calc R . . C3 C -0.22953(16) 0.3843(3) 0.45679(12) 0.0430(6) Uani 1 1 d . . . H3 H -0.2431 0.4081 0.4115 0.052 Uiso 1 1 calc R . . C4 C -0.1428(2) 0.3238(4) 0.49966(13) 0.0506(6) Uani 1 1 d . . . C5 C -0.06294(19) 0.2854(3) 0.47735(12) 0.0476(6) Uani 1 1 d . . . C6 C -0.0588(2) 0.2869(4) 0.41205(13) 0.0522(7) Uani 1 1 d . . . H6 H -0.1089 0.3161 0.3734 0.063 Uiso 1 1 calc R . . C7 C 0.0330(2) 0.2374(4) 0.41610(13) 0.0513(6) Uani 1 1 d . . . C8 C 0.0867(2) 0.2057(3) 0.48426(12) 0.0495(6) Uani 1 1 d . . . C9 C 0.0124(3) 0.2638(6) 0.30238(15) 0.0817(10) Uani 1 1 d . . . H9A H -0.0415 0.1782 0.2893 0.123 Uiso 1 1 calc R . . H9B H 0.0483 0.2514 0.2720 0.123 Uiso 1 1 calc R . . H9C H -0.0100 0.3929 0.3015 0.123 Uiso 1 1 calc R . . C10 C 0.1807(2) 0.1510(4) 0.50913(13) 0.0512(6) Uani 1 1 d . . . H10 H 0.2137 0.1357 0.4787 0.061 Uiso 1 1 calc R . . C11 C 0.32394(18) 0.0499(4) 0.59739(12) 0.0486(6) Uani 1 1 d . . . C12 C 0.35134(19) -0.0462(4) 0.65679(12) 0.0532(7) Uani 1 1 d . . . H12 H 0.3095 -0.0552 0.6815 0.064 Uiso 1 1 calc R . . C13 C 0.4406(2) -0.1293(4) 0.68009(13) 0.0577(7) Uani 1 1 d . . . H13 H 0.4571 -0.1979 0.7198 0.069 Uiso 1 1 calc R . . C14 C 0.5069(2) -0.1145(4) 0.64640(13) 0.0578(7) Uani 1 1 d . . . C15 C 0.4793(2) -0.0068(6) 0.58907(15) 0.0745(9) Uani 1 1 d . . . H15 H 0.5228 0.0117 0.5661 0.089 Uiso 1 1 calc R . . C16 C 0.3897(2) 0.0746(5) 0.56443(15) 0.0713(9) Uani 1 1 d . . . H16 H 0.3735 0.1465 0.5254 0.086 Uiso 1 1 calc R . . C17 C 0.6023(2) -0.2222(6) 0.67210(16) 0.0731(9) Uani 1 1 d . . . C18 C 0.6738(3) -0.1607(10) 0.6382(3) 0.137(2) Uani 1 1 d . . . H18A H 0.7309 -0.2370 0.6545 0.205 Uiso 1 1 calc R . . H18B H 0.6898 -0.0284 0.6479 0.205 Uiso 1 1 calc R . . H18C H 0.6460 -0.1776 0.5909 0.205 Uiso 1 1 calc R . . C19 C 0.6480(3) -0.1961(10) 0.7467(2) 0.141(2) Uani 1 1 d . . . H19A H 0.7116 -0.2487 0.7606 0.211 Uiso 1 1 calc R . . H19B H 0.6101 -0.2606 0.7694 0.211 Uiso 1 1 calc R . . H19C H 0.6512 -0.0622 0.7573 0.211 Uiso 1 1 calc R . . C20 C 0.5818(3) -0.4359(8) 0.6597(3) 0.1338(19) Uani 1 1 d . . . H20A H 0.5683 -0.4631 0.6131 0.201 Uiso 1 1 calc R . . H20B H 0.5275 -0.4706 0.6729 0.201 Uiso 1 1 calc R . . H20C H 0.6369 -0.5081 0.6853 0.201 Uiso 1 1 calc R . . H2A H 0.231(3) 0.420(6) 0.688(2) 0.145(19) Uiso 1 1 d D . . H2B H 0.296(3) 0.555(6) 0.7217(13) 0.124(15) Uiso 1 1 d 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 O2 0.113(2) 0.0957(19) 0.0532(13) 0.0003(13) 0.0003(13) -0.0333(16) Cl1 0.0735(5) 0.0732(5) 0.0380(4) -0.0003(3) 0.0167(3) 0.0025(3) N1 0.104(2) 0.088(2) 0.0643(17) -0.0033(14) 0.0279(16) 0.0087(17) N2 0.0623(14) 0.0446(12) 0.0338(10) -0.0020(9) 0.0086(10) 0.0016(10) N3 0.0585(13) 0.0546(13) 0.0429(12) -0.0025(10) 0.0162(10) 0.0039(10) O1 0.0765(14) 0.0797(14) 0.0435(11) -0.0019(9) 0.0213(10) -0.0007(11) C1 0.081(2) 0.092(3) 0.077(2) -0.0091(19) 0.0393(19) 0.0092(19) C2 0.0641(18) 0.072(2) 0.079(2) -0.0051(17) 0.0148(17) 0.0040(16) C3 0.0441(13) 0.0430(13) 0.0372(12) -0.0047(10) 0.0066(10) -0.0005(10) C4 0.0667(17) 0.0398(13) 0.0421(14) -0.0074(10) 0.0129(13) -0.0003(12) C5 0.0603(16) 0.0371(13) 0.0403(13) -0.0035(10) 0.0091(12) -0.0015(11) C6 0.0646(17) 0.0488(15) 0.0366(13) -0.0014(11) 0.0074(12) 0.0007(12) C7 0.0648(17) 0.0458(14) 0.0419(14) -0.0032(11) 0.0153(12) -0.0033(12) C8 0.0637(17) 0.0414(14) 0.0405(13) -0.0032(10) 0.0128(12) -0.0021(12) C9 0.095(3) 0.104(3) 0.0443(17) 0.0074(17) 0.0210(17) -0.004(2) C10 0.0650(17) 0.0431(14) 0.0433(14) -0.0020(11) 0.0147(12) -0.0017(12) C11 0.0536(15) 0.0478(14) 0.0439(13) -0.0018(11) 0.0154(11) -0.0001(12) C12 0.0536(15) 0.0671(17) 0.0405(13) -0.0009(12) 0.0174(11) -0.0039(13) C13 0.0585(16) 0.0709(18) 0.0399(14) 0.0055(13) 0.0108(12) -0.0003(14) C14 0.0577(16) 0.0718(18) 0.0441(14) -0.0038(13) 0.0166(12) 0.0002(14) C15 0.0643(18) 0.106(3) 0.0611(18) 0.0156(18) 0.0311(15) 0.0066(18) C16 0.075(2) 0.089(2) 0.0549(17) 0.0224(16) 0.0269(15) 0.0118(18) C17 0.0599(19) 0.101(3) 0.0575(19) 0.0005(16) 0.0178(15) 0.0127(17) C18 0.071(3) 0.219(6) 0.127(4) 0.046(4) 0.043(3) 0.033(3) C19 0.087(3) 0.236(7) 0.076(3) -0.014(3) -0.005(2) 0.065(4) C20 0.103(3) 0.109(4) 0.181(5) 0.001(4) 0.033(3) 0.038(3) _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 O2 H2A 0.933(19) . ? O2 H2B 0.908(19) . ? N1 C4 1.369(4) . ? N1 C1 1.389(5) . ? N1 H1A 0.8600 . ? N2 C5 1.339(3) . ? N2 C8 1.382(3) . ? N2 H2C 0.8600 . ? N3 C10 1.319(3) . ? N3 C11 1.409(3) . ? N3 H3A 0.8600 . ? O1 C7 1.326(3) . ? O1 C9 1.434(4) . ? C1 C2 1.365(5) . ? C1 H1 0.9300 . ? C2 C3 1.331(4) . ? C2 H2 0.9300 . ? C3 C4 1.372(4) . ? C3 H3 0.9300 . ? C4 C5 1.427(4) . ? C5 C6 1.404(4) . ? C6 C7 1.371(4) . ? C6 H6 0.9300 . ? C7 C8 1.420(4) . ? C8 C10 1.367(4) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10 0.9300 . ? C11 C12 1.367(4) . ? C11 C16 1.376(4) . ? C12 C13 1.374(4) . ? C12 H12 0.9300 . ? C13 C14 1.387(4) . ? C13 H13 0.9300 . ? C14 C15 1.374(4) . ? C14 C17 1.530(4) . ? C15 C16 1.375(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C19 1.513(5) . ? C17 C18 1.515(5) . ? C17 C20 1.531(7) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 H2A O2 H2B 97(3) . . ? C4 N1 C1 107.7(3) . . ? C4 N1 H1A 126.2 . . ? C1 N1 H1A 126.2 . . ? C5 N2 C8 110.1(2) . . ? C5 N2 H2C 125.0 . . ? C8 N2 H2C 125.0 . . ? C10 N3 C11 125.5(2) . . ? C10 N3 H3A 117.2 . . ? C11 N3 H3A 117.2 . . ? C7 O1 C9 115.5(2) . . ? C2 C1 N1 106.9(3) . . ? C2 C1 H1 126.6 . . ? N1 C1 H1 126.6 . . ? C3 C2 C1 109.1(3) . . ? C3 C2 H2 125.4 . . ? C1 C2 H2 125.4 . . ? C2 C3 C4 109.0(2) . . ? C2 C3 H3 125.5 . . ? C4 C3 H3 125.5 . . ? N1 C4 C3 107.3(3) . . ? N1 C4 C5 130.8(3) . . ? C3 C4 C5 121.9(2) . . ? N2 C5 C6 108.7(2) . . ? N2 C5 C4 122.4(2) . . ? C6 C5 C4 128.9(2) . . ? C7 C6 C5 107.0(2) . . ? C7 C6 H6 126.5 . . ? C5 C6 H6 126.5 . . ? O1 C7 C6 130.4(2) . . ? O1 C7 C8 121.2(3) . . ? C6 C7 C8 108.4(2) . . ? C10 C8 N2 127.6(2) . . ? C10 C8 C7 126.5(3) . . ? N2 C8 C7 105.8(2) . . ? O1 C9 H9A 109.5 . . ? O1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 C8 125.8(3) . . ? N3 C10 H10 117.1 . . ? C8 C10 H10 117.1 . . ? C12 C11 C16 118.9(2) . . ? C12 C11 N3 118.2(2) . . ? C16 C11 N3 123.0(2) . . ? C11 C12 C13 120.1(2) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C14 122.3(3) . . ? C12 C13 H13 118.9 . . ? C14 C13 H13 118.9 . . ? C15 C14 C13 116.1(3) . . ? C15 C14 C17 123.9(3) . . ? C13 C14 C17 119.9(3) . . ? C14 C15 C16 122.3(3) . . ? C14 C15 H15 118.8 . . ? C16 C15 H15 118.8 . . ? C15 C16 C11 120.1(3) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? C19 C17 C18 108.5(4) . . ? C19 C17 C14 111.0(3) . . ? C18 C17 C14 113.0(3) . . ? C19 C17 C20 107.0(4) . . ? C18 C17 C20 108.9(4) . . ? C14 C17 C20 108.2(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 0.1(4) . . . . ? N1 C1 C2 C3 -0.3(4) . . . . ? C1 C2 C3 C4 0.4(4) . . . . ? C1 N1 C4 C3 0.2(3) . . . . ? C1 N1 C4 C5 -178.2(3) . . . . ? C2 C3 C4 N1 -0.3(3) . . . . ? C2 C3 C4 C5 178.2(3) . . . . ? C8 N2 C5 C6 -0.3(3) . . . . ? C8 N2 C5 C4 179.0(2) . . . . ? N1 C4 C5 N2 -6.1(4) . . . . ? C3 C4 C5 N2 175.8(2) . . . . ? N1 C4 C5 C6 173.1(3) . . . . ? C3 C4 C5 C6 -5.0(4) . . . . ? N2 C5 C6 C7 0.4(3) . . . . ? C4 C5 C6 C7 -178.9(3) . . . . ? C9 O1 C7 C6 3.7(4) . . . . ? C9 O1 C7 C8 -176.6(3) . . . . ? C5 C6 C7 O1 179.4(3) . . . . ? C5 C6 C7 C8 -0.3(3) . . . . ? C5 N2 C8 C10 -178.7(3) . . . . ? C5 N2 C8 C7 0.1(3) . . . . ? O1 C7 C8 C10 -0.8(4) . . . . ? C6 C7 C8 C10 178.9(3) . . . . ? O1 C7 C8 N2 -179.6(2) . . . . ? C6 C7 C8 N2 0.1(3) . . . . ? C11 N3 C10 C8 175.6(2) . . . . ? N2 C8 C10 N3 0.2(4) . . . . ? C7 C8 C10 N3 -178.4(3) . . . . ? C10 N3 C11 C12 -154.8(3) . . . . ? C10 N3 C11 C16 24.8(4) . . . . ? C16 C11 C12 C13 -5.2(4) . . . . ? N3 C11 C12 C13 174.4(2) . . . . ? C11 C12 C13 C14 2.2(4) . . . . ? C12 C13 C14 C15 1.8(5) . . . . ? C12 C13 C14 C17 -175.6(3) . . . . ? C13 C14 C15 C16 -3.0(5) . . . . ? C17 C14 C15 C16 174.3(3) . . . . ? C14 C15 C16 C11 0.1(6) . . . . ? C12 C11 C16 C15 4.0(5) . . . . ? N3 C11 C16 C15 -175.5(3) . . . . ? C15 C14 C17 C19 136.3(4) . . . . ? C13 C14 C17 C19 -46.5(5) . . . . ? C15 C14 C17 C18 14.2(5) . . . . ? C13 C14 C17 C18 -168.6(4) . . . . ? C15 C14 C17 C20 -106.5(4) . . . . ? C13 C14 C17 C20 70.7(4) . . . . ? 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 O2 H2B Cl1 0.908(19) 2.33(2) 3.223(3) 168(4) 2_556 O2 H2A Cl1 0.933(19) 2.26(2) 3.166(3) 163(4) . N3 H3A Cl1 0.86 2.35 3.210(2) 178.2 . N2 H2C Cl1 0.86 2.34 3.183(2) 165.6 . N1 H1A Cl1 0.86 3.23 3.996(4) 149.0 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.512 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.053