Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_section_title ;A diversity orientated approach to functionalised pyridazinones ; _publ_contact_author_name 'Joseph Harrity' _publ_contact_author_email J.HARRITY@SHEFFIELD.AC.UK loop_ _publ_author_name 'Joseph Harrity' 'Matthew D. Helm' 'Andrew Plant' data_ohj78_0m _database_code_depnum_ccdc_archive 'CCDC 620790' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H15 Cl N2 O2' _chemical_formula_weight 278.73 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.227(2) _cell_length_b 12.144(3) _cell_length_c 12.904(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.550(15) _cell_angle_gamma 90.00 _cell_volume 1445.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1835 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 22.80 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.264 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9590 _exptl_absorpt_correction_T_max 0.9895 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'apex2 area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11319 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 27.62 _reflns_number_total 3280 _reflns_number_gt 1865 _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^)+(0.0605P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3280 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0916 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1266 _refine_ls_wR_factor_gt 0.1055 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _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 0.42904(7) 0.44579(5) 0.15126(5) 0.0816(3) Uani 1 1 d . . . N1 N 0.55625(18) 0.32228(13) 0.28546(12) 0.0534(4) Uani 1 1 d . . . N2 N 0.65159(18) 0.24359(13) 0.31456(12) 0.0501(4) Uani 1 1 d . . . H2 H 0.6462 0.2253 0.3888 0.087(8) Uiso 1 1 d R . . O1 O 0.61488(17) 0.31862(11) 0.01315(10) 0.0654(5) Uani 1 1 d . . . O2 O 0.81789(14) 0.10848(11) 0.29183(11) 0.0583(4) Uani 1 1 d . . . C1 C 0.5498(2) 0.34426(15) 0.18732(15) 0.0481(5) Uani 1 1 d . . . C2 C 0.6312(2) 0.29094(15) 0.10603(14) 0.0459(5) Uani 1 1 d . . . C3 C 0.7284(2) 0.20712(15) 0.14273(14) 0.0453(5) Uani 1 1 d . . . C4 C 0.7337(2) 0.18904(15) 0.24687(15) 0.0445(5) Uani 1 1 d . . . C5 C 0.9600(2) 0.13492(18) 0.32356(14) 0.0509(5) Uani 1 1 d . . . C6 C 1.0351(3) 0.0497(2) 0.37113(18) 0.0741(7) Uani 1 1 d . . . H6 H 0.9919 -0.0187 0.3796 0.089 Uiso 1 1 calc R . . C7 C 1.1763(3) 0.0685(3) 0.4060(2) 0.0974(10) Uani 1 1 d . . . H7 H 1.2290 0.0119 0.4377 0.117 Uiso 1 1 calc R . . C8 C 1.2382(3) 0.1697(3) 0.3941(2) 0.1011(11) Uani 1 1 d . . . H8 H 1.3325 0.1818 0.4189 0.121 Uiso 1 1 calc R . . C9 C 1.1637(3) 0.2532(3) 0.3465(2) 0.0856(8) Uani 1 1 d . . . H9 H 1.2077 0.3214 0.3378 0.103 Uiso 1 1 calc R . . C10 C 1.0202(2) 0.2363(2) 0.31042(18) 0.0641(6) Uani 1 1 d . . . H10 H 0.9678 0.2929 0.2784 0.077 Uiso 1 1 calc R . . C11 C 0.8103(2) 0.13814(18) 0.06699(16) 0.0580(6) Uani 1 1 d . . . H11A H 0.8926 0.1039 0.1025 0.070 Uiso 1 1 calc R . . H11B H 0.8469 0.1851 0.0128 0.070 Uiso 1 1 calc R . . C12 C 0.7130(2) 0.04845(17) 0.01807(17) 0.0584(6) Uani 1 1 d . . . H12A H 0.6780 0.0013 0.0727 0.070 Uiso 1 1 calc R . . H12B H 0.6294 0.0833 -0.0153 0.070 Uiso 1 1 calc R . . C13 C 0.7882(3) -0.0221(2) -0.0608(2) 0.0785(7) Uani 1 1 d . . . H13A H 0.8256 0.0250 -0.1146 0.094 Uiso 1 1 calc R . . H13B H 0.8700 -0.0590 -0.0271 0.094 Uiso 1 1 calc R . . C14 C 0.6893(3) -0.1075(2) -0.1102(2) 0.0929(9) Uani 1 1 d . . . H14A H 0.6497 -0.1532 -0.0572 0.139 Uiso 1 1 calc R . . H14B H 0.7435 -0.1523 -0.1566 0.139 Uiso 1 1 calc R . . H14C H 0.6120 -0.0714 -0.1480 0.139 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 Cl1 0.0899(5) 0.0829(4) 0.0708(4) -0.0129(3) -0.0194(3) 0.0445(3) N1 0.0555(11) 0.0653(11) 0.0392(10) -0.0074(8) -0.0015(8) 0.0089(9) N2 0.0545(11) 0.0640(11) 0.0315(9) 0.0012(8) -0.0024(8) 0.0003(9) O1 0.0924(12) 0.0732(10) 0.0302(8) 0.0002(7) -0.0043(7) 0.0188(8) O2 0.0481(9) 0.0583(9) 0.0677(10) 0.0172(7) -0.0132(7) -0.0021(7) C1 0.0491(12) 0.0542(11) 0.0406(11) -0.0080(9) -0.0058(9) 0.0093(9) C2 0.0513(12) 0.0526(11) 0.0334(11) -0.0046(9) -0.0044(9) 0.0023(9) C3 0.0425(11) 0.0527(11) 0.0405(11) -0.0007(9) -0.0002(8) 0.0037(9) C4 0.0388(11) 0.0479(10) 0.0462(12) 0.0029(9) -0.0081(9) -0.0013(9) C5 0.0409(12) 0.0727(13) 0.0388(11) 0.0005(10) -0.0069(9) 0.0079(10) C6 0.0687(16) 0.0922(18) 0.0606(15) 0.0093(13) -0.0115(12) 0.0200(13) C7 0.0681(19) 0.144(3) 0.079(2) 0.0066(19) -0.0213(15) 0.0343(19) C8 0.0540(18) 0.167(3) 0.081(2) -0.022(2) -0.0207(15) 0.013(2) C9 0.0603(17) 0.116(2) 0.0802(19) -0.0204(16) -0.0018(14) -0.0204(16) C10 0.0520(14) 0.0781(15) 0.0620(14) -0.0075(12) -0.0037(11) -0.0034(12) C11 0.0529(13) 0.0702(14) 0.0511(13) 0.0001(11) 0.0076(10) 0.0143(11) C12 0.0593(14) 0.0616(13) 0.0544(13) -0.0063(10) 0.0057(10) 0.0113(11) C13 0.0737(17) 0.0832(16) 0.0795(18) -0.0175(14) 0.0164(13) 0.0158(14) C14 0.106(2) 0.0841(18) 0.089(2) -0.0325(15) 0.0106(17) 0.0031(16) _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 Cl1 C1 1.7176(19) . ? N1 C1 1.294(2) . ? N1 N2 1.346(2) . ? N2 C4 1.346(2) . ? N2 H2 0.9859 . ? O1 C2 1.250(2) . ? O2 C4 1.369(2) . ? O2 C5 1.401(2) . ? C1 C2 1.458(3) . ? C2 C3 1.429(2) . ? C3 C4 1.361(3) . ? C3 C11 1.506(3) . ? C5 C10 1.364(3) . ? C5 C6 1.380(3) . ? C6 C7 1.386(3) . ? C6 H6 0.9300 . ? C7 C8 1.367(4) . ? C7 H7 0.9300 . ? C8 C9 1.362(4) . ? C8 H8 0.9300 . ? C9 C10 1.406(3) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.536(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.513(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.511(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 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 N2 115.59(16) . . ? N1 N2 C4 122.93(16) . . ? N1 N2 H2 112.4 . . ? C4 N2 H2 124.3 . . ? C4 O2 C5 118.45(15) . . ? N1 C1 C2 126.97(17) . . ? N1 C1 Cl1 115.18(15) . . ? C2 C1 Cl1 117.84(14) . . ? O1 C2 C3 124.60(18) . . ? O1 C2 C1 121.27(17) . . ? C3 C2 C1 114.13(16) . . ? C4 C3 C2 116.59(17) . . ? C4 C3 C11 123.07(17) . . ? C2 C3 C11 120.18(17) . . ? N2 C4 C3 123.75(17) . . ? N2 C4 O2 113.56(16) . . ? C3 C4 O2 122.59(18) . . ? C10 C5 C6 122.1(2) . . ? C10 C5 O2 123.51(18) . . ? C6 C5 O2 114.39(19) . . ? C5 C6 C7 118.5(3) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C8 C7 C6 120.2(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C9 C8 C7 120.9(3) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 120.0(3) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C5 C10 C9 118.3(2) . . ? C5 C10 H10 120.9 . . ? C9 C10 H10 120.9 . . ? C3 C11 C12 111.30(17) . . ? C3 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? C3 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C13 C12 C11 113.87(18) . . ? C13 C12 H12A 108.8 . . ? C11 C12 H12A 108.8 . . ? C13 C12 H12B 108.8 . . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C12 113.0(2) . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13B 109.0 . . ? C12 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.62 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.218 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.035 # Attachment 'ohj84.cif' data_ohj84 _database_code_depnum_ccdc_archive 'CCDC 620791' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 Cl N3 O4' _chemical_formula_weight 411.83 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 Tetragonal _symmetry_space_group_name_H-M P4/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y+1/2, x, z' 'y, -x+1/2, z' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y-1/2, -x, -z' '-y, x-1/2, -z' _cell_length_a 25.7394(10) _cell_length_b 25.7394(10) _cell_length_c 5.9168(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3920.0(5) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3469 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 19.83 _exptl_crystal_description NEEDLE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9600 _exptl_absorpt_correction_T_max 0.9864 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 53474 _diffrn_reflns_av_R_equivalents 0.1151 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3445 _reflns_number_gt 2407 _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^)+(0.0469P)^2^+2.7885P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3445 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0801 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 Cl1 Cl 1.07694(3) 0.29855(3) 0.29056(13) 0.0377(2) Uani 1 1 d . . . N1 N 1.00185(9) 0.32784(8) 0.5440(4) 0.0261(5) Uani 1 1 d . . . N2 N 0.96464(8) 0.32339(8) 0.7017(4) 0.0242(5) Uani 1 1 d . . . N3 N 0.92711(9) -0.04133(9) 1.2129(4) 0.0273(5) Uani 1 1 d . . . O1 O 0.97804(7) 0.18745(6) 0.8654(3) 0.0211(4) Uani 1 1 d . . . O2 O 0.93255(7) 0.15901(7) 0.5636(3) 0.0278(5) Uani 1 1 d . . . O3 O 0.95222(7) -0.04921(7) 1.3854(3) 0.0320(5) Uani 1 1 d . . . O4 O 0.89687(9) -0.07288(8) 1.1317(4) 0.0430(6) Uani 1 1 d . . . C1 C 1.03042(10) 0.28668(10) 0.4954(5) 0.0244(6) Uani 1 1 d . . . C2 C 0.95664(10) 0.27815(9) 0.8069(4) 0.0200(6) Uani 1 1 d . . . C3 C 0.98661(10) 0.23446(9) 0.7518(4) 0.0200(6) Uani 1 1 d . . . C4 C 1.02505(10) 0.23717(10) 0.5898(5) 0.0229(6) Uani 1 1 d . . . C5 C 0.94936(10) 0.15089(10) 0.7491(5) 0.0208(6) Uani 1 1 d . . . C6 C 0.94420(9) 0.10180(10) 0.8783(4) 0.0195(6) Uani 1 1 d . . . C7 C 0.91479(10) 0.06251(10) 0.7784(4) 0.0213(6) Uani 1 1 d . . . H7 H 0.8986 0.0681 0.6362 0.026 Uiso 1 1 calc R . . C8 C 0.90932(10) 0.01513(10) 0.8884(4) 0.0221(6) Uani 1 1 d . . . H8 H 0.8896 -0.0122 0.8228 0.027 Uiso 1 1 calc R . . C9 C 0.93323(10) 0.00884(9) 1.0955(4) 0.0206(6) Uani 1 1 d . . . C10 C 0.96248(10) 0.04727(10) 1.1983(5) 0.0217(6) Uani 1 1 d . . . H10 H 0.9785 0.0415 1.3409 0.026 Uiso 1 1 calc R . . C11 C 0.96770(10) 0.09431(10) 1.0872(4) 0.0213(6) Uani 1 1 d . . . H11 H 0.9874 0.1215 1.1538 0.026 Uiso 1 1 calc R . . C12 C 0.91371(10) 0.27894(9) 0.9749(4) 0.0201(6) Uani 1 1 d . . . C13 C 0.91582(10) 0.25135(10) 1.1786(4) 0.0216(6) Uani 1 1 d . . . H13 H 0.9449 0.2298 1.2104 0.026 Uiso 1 1 calc R . . C14 C 0.87587(10) 0.25537(10) 1.3338(5) 0.0241(6) Uani 1 1 d . . . H14 H 0.8777 0.2368 1.4723 0.029 Uiso 1 1 calc R . . C15 C 0.83299(10) 0.28648(10) 1.2878(5) 0.0264(6) Uani 1 1 d . . . H15 H 0.8055 0.2891 1.3944 0.032 Uiso 1 1 calc R . . C16 C 0.83052(11) 0.31352(10) 1.0869(5) 0.0271(6) Uani 1 1 d . . . H16 H 0.8011 0.3347 1.0552 0.033 Uiso 1 1 calc R . . C17 C 0.87039(10) 0.31016(10) 0.9310(5) 0.0241(6) Uani 1 1 d . . . H17 H 0.8684 0.3291 0.7936 0.029 Uiso 1 1 calc R . . C18 C 1.05840(11) 0.19155(11) 0.5194(5) 0.0304(7) Uani 1 1 d . . . H18A H 1.0612 0.1913 0.3525 0.036 Uiso 1 1 calc R . . H18B H 1.0409 0.1590 0.5658 0.036 Uiso 1 1 calc R . . C19 C 1.11307(11) 0.19212(12) 0.6195(5) 0.0376(8) Uani 1 1 d . . . H19A H 1.1316 0.1603 0.5710 0.045 Uiso 1 1 calc R . . H19B H 1.1322 0.2223 0.5578 0.045 Uiso 1 1 calc R . . C20 C 1.11394(12) 0.19494(12) 0.8712(6) 0.0400(8) Uani 1 1 d . . . H20A H 1.0908 0.1677 0.9333 0.048 Uiso 1 1 calc R . . H20B H 1.1002 0.2291 0.9196 0.048 Uiso 1 1 calc R . . C21 C 1.16864(13) 0.18764(13) 0.9686(7) 0.0542(10) Uani 1 1 d . . . H21A H 1.1815 0.1530 0.9293 0.081 Uiso 1 1 calc R . . H21B H 1.1674 0.1913 1.1334 0.081 Uiso 1 1 calc R . . H21C H 1.1919 0.2140 0.9054 0.081 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 Cl1 0.0395(4) 0.0345(4) 0.0392(5) 0.0121(4) 0.0150(4) 0.0031(3) N1 0.0291(13) 0.0231(12) 0.0261(13) 0.0021(10) -0.0002(11) -0.0031(10) N2 0.0260(12) 0.0203(12) 0.0263(13) 0.0005(10) -0.0010(11) -0.0009(10) N3 0.0303(13) 0.0236(13) 0.0281(14) 0.0044(11) 0.0010(11) 0.0030(11) O1 0.0257(10) 0.0159(9) 0.0218(10) 0.0027(8) -0.0006(8) -0.0013(8) O2 0.0347(11) 0.0248(10) 0.0240(11) 0.0035(8) -0.0068(9) -0.0021(9) O3 0.0326(11) 0.0312(11) 0.0321(12) 0.0108(9) -0.0087(10) 0.0024(9) O4 0.0586(15) 0.0276(12) 0.0428(14) 0.0062(10) -0.0160(12) -0.0179(11) C1 0.0243(15) 0.0240(15) 0.0249(15) 0.0027(12) 0.0007(12) -0.0034(12) C2 0.0223(14) 0.0179(13) 0.0197(14) -0.0002(11) -0.0056(11) -0.0012(11) C3 0.0239(14) 0.0159(13) 0.0201(14) 0.0015(11) -0.0044(12) -0.0016(11) C4 0.0228(14) 0.0208(14) 0.0250(15) -0.0008(12) -0.0009(12) -0.0008(11) C5 0.0185(13) 0.0191(14) 0.0250(15) -0.0024(12) 0.0004(12) 0.0030(11) C6 0.0173(13) 0.0205(14) 0.0208(14) 0.0021(11) 0.0018(11) 0.0028(11) C7 0.0201(13) 0.0241(14) 0.0197(14) 0.0029(12) -0.0016(11) 0.0038(11) C8 0.0212(14) 0.0196(14) 0.0254(15) -0.0034(12) -0.0006(12) -0.0005(11) C9 0.0205(14) 0.0185(14) 0.0228(15) 0.0025(11) 0.0035(12) 0.0032(11) C10 0.0206(14) 0.0228(14) 0.0217(14) 0.0004(12) -0.0025(12) 0.0027(11) C11 0.0203(14) 0.0206(14) 0.0230(14) -0.0017(12) -0.0013(12) -0.0018(11) C12 0.0225(14) 0.0161(13) 0.0217(14) -0.0030(11) -0.0027(12) -0.0005(11) C13 0.0208(14) 0.0220(14) 0.0220(14) -0.0013(12) -0.0038(12) 0.0007(11) C14 0.0260(15) 0.0228(14) 0.0236(15) -0.0001(12) -0.0028(12) -0.0006(12) C15 0.0277(15) 0.0269(15) 0.0247(15) -0.0025(13) 0.0037(13) 0.0012(12) C16 0.0242(15) 0.0264(15) 0.0307(16) -0.0002(13) -0.0018(13) 0.0050(12) C17 0.0311(16) 0.0168(13) 0.0244(15) 0.0017(12) -0.0030(12) 0.0008(12) C18 0.0359(17) 0.0268(16) 0.0284(17) 0.0037(13) 0.0107(13) 0.0048(13) C19 0.0302(17) 0.0310(17) 0.051(2) 0.0114(15) 0.0116(15) 0.0061(13) C20 0.0357(18) 0.0288(17) 0.056(2) -0.0063(16) -0.0056(16) 0.0044(14) C21 0.043(2) 0.040(2) 0.080(3) 0.0079(19) -0.017(2) 0.0074(16) _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 Cl1 C1 1.731(3) . ? N1 C1 1.321(3) . ? N1 N2 1.342(3) . ? N2 C2 1.336(3) . ? N3 O4 1.223(3) . ? N3 O3 1.225(3) . ? N3 C9 1.475(3) . ? O1 C5 1.380(3) . ? O1 C3 1.402(3) . ? O2 C5 1.198(3) . ? C1 C4 1.398(4) . ? C2 C3 1.402(3) . ? C2 C12 1.487(4) . ? C3 C4 1.379(4) . ? C4 C18 1.513(4) . ? C5 C6 1.482(3) . ? C6 C11 1.390(4) . ? C6 C7 1.394(4) . ? C7 C8 1.389(4) . ? C7 H7 0.9500 . ? C8 C9 1.381(4) . ? C8 H8 0.9500 . ? C9 C10 1.384(3) . ? C10 C11 1.385(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C17 1.399(4) . ? C12 C13 1.400(3) . ? C13 C14 1.382(4) . ? C13 H13 0.9500 . ? C14 C15 1.390(4) . ? C14 H14 0.9500 . ? C15 C16 1.379(4) . ? C15 H15 0.9500 . ? C16 C17 1.382(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.527(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.491(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.533(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 N2 118.7(2) . . ? C2 N2 N1 120.5(2) . . ? O4 N3 O3 123.6(2) . . ? O4 N3 C9 117.7(2) . . ? O3 N3 C9 118.8(2) . . ? C5 O1 C3 115.72(19) . . ? N1 C1 C4 126.1(2) . . ? N1 C1 Cl1 113.3(2) . . ? C4 C1 Cl1 120.6(2) . . ? N2 C2 C3 120.4(2) . . ? N2 C2 C12 114.5(2) . . ? C3 C2 C12 125.1(2) . . ? C4 C3 O1 119.3(2) . . ? C4 C3 C2 121.0(2) . . ? O1 C3 C2 119.6(2) . . ? C3 C4 C1 113.2(2) . . ? C3 C4 C18 124.0(2) . . ? C1 C4 C18 122.8(2) . . ? O2 C5 O1 122.1(2) . . ? O2 C5 C6 126.1(2) . . ? O1 C5 C6 111.9(2) . . ? C11 C6 C7 120.8(2) . . ? C11 C6 C5 122.5(2) . . ? C7 C6 C5 116.7(2) . . ? C8 C7 C6 119.6(2) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C9 C8 C7 118.2(2) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? C8 C9 C10 123.3(2) . . ? C8 C9 N3 118.2(2) . . ? C10 C9 N3 118.5(2) . . ? C11 C10 C9 118.0(2) . . ? C11 C10 H10 121.0 . . ? C9 C10 H10 121.0 . . ? C10 C11 C6 120.1(2) . . ? C10 C11 H11 119.9 . . ? C6 C11 H11 119.9 . . ? C17 C12 C13 118.8(2) . . ? C17 C12 C2 118.4(2) . . ? C13 C12 C2 122.7(2) . . ? C14 C13 C12 120.3(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 120.3(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 119.7(3) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 120.6(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C12 120.3(3) . . ? C16 C17 H17 119.9 . . ? C12 C17 H17 119.9 . . ? C4 C18 C19 114.1(2) . . ? C4 C18 H18A 108.7 . . ? C19 C18 H18A 108.7 . . ? C4 C18 H18B 108.7 . . ? C19 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C20 C19 C18 113.7(3) . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19A 108.8 . . ? C20 C19 H19B 108.8 . . ? C18 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C19 C20 C21 112.5(3) . . ? C19 C20 H20A 109.1 . . ? C21 C20 H20A 109.1 . . ? C19 C20 H20B 109.1 . . ? C21 C20 H20B 109.1 . . ? H20A C20 H20B 107.8 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.340 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.053