# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_compound1 _database_code_depnum_ccdc_archive 'CCDC 819257' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 Cl N3 O' _chemical_formula_weight 264.73 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1813(14) _cell_length_b 11.4717(15) _cell_length_c 13.7287(18) _cell_angle_alpha 92.490(2) _cell_angle_beta 91.719(2) _cell_angle_gamma 107.966(2) _cell_volume 1522.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 7395 _cell_measurement_theta_min 1.87 _cell_measurement_theta_max 25.34 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.155 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 0.244 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.935 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(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 'Bruker APEX CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7395 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0591 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.34 _reflns_number_total 5419 _reflns_number_gt 3465 _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^)+(0.1365P)^2^] 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 5419 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1146 _refine_ls_R_factor_gt 0.0779 _refine_ls_wR_factor_ref 0.2315 _refine_ls_wR_factor_gt 0.2134 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 C1 C 0.2948(3) 0.4329(3) 0.3565(3) 0.0380(8) Uani 1 1 d . . . C2 C 0.4186(3) 0.5293(3) 0.3771(3) 0.0395(9) Uani 1 1 d . . . C3 C 0.3899(4) 0.5977(3) 0.4535(3) 0.0421(9) Uani 1 1 d . . . C4 C 0.4786(4) 0.7104(4) 0.5085(3) 0.0568(11) Uani 1 1 d . . . H4A H 0.4675 0.7830 0.4785 0.085 Uiso 1 1 calc R . . H4B H 0.5755 0.7127 0.5069 0.085 Uiso 1 1 calc R . . H4C H 0.4513 0.7099 0.5763 0.085 Uiso 1 1 calc R . . C5 C 0.5550(3) 0.5510(4) 0.3292(3) 0.0405(9) Uani 1 1 d . . . H5A H 0.5645 0.4705 0.3080 0.049 Uiso 1 1 calc R . . H5B H 0.6305 0.5902 0.3785 0.049 Uiso 1 1 calc R . . C6 C 0.5736(3) 0.6310(3) 0.2411(3) 0.0412(9) Uani 1 1 d . . . H6A H 0.5735 0.7141 0.2635 0.049 Uiso 1 1 calc R . . H6B H 0.6652 0.6388 0.2147 0.049 Uiso 1 1 calc R . . C7 C 0.4648(4) 0.5831(3) 0.1600(3) 0.0414(9) Uani 1 1 d . . . H7A H 0.3758 0.5898 0.1826 0.050 Uiso 1 1 calc R . . H7B H 0.4906 0.6356 0.1039 0.050 Uiso 1 1 calc R . . C8 C 0.1706(4) 0.2391(3) 0.2556(3) 0.0401(9) Uani 1 1 d . . . C9 C 0.0454(4) 0.2021(4) 0.3008(3) 0.0552(12) Uani 1 1 d . . . H9 H 0.0300 0.2499 0.3549 0.066 Uiso 1 1 calc R . . C10 C -0.0556(4) 0.0977(4) 0.2681(4) 0.0719(15) Uani 1 1 d . . . H10 H -0.1390 0.0719 0.3018 0.086 Uiso 1 1 calc R . . C11 C -0.0393(4) 0.0283(4) 0.1866(4) 0.0689(14) Uani 1 1 d . . . C12 C 0.0847(4) 0.0620(4) 0.1424(4) 0.0606(13) Uani 1 1 d . . . H12 H 0.0997 0.0135 0.0886 0.073 Uiso 1 1 calc R . . C13 C 0.1874(4) 0.1664(3) 0.1763(3) 0.0491(10) Uani 1 1 d . . . H13 H 0.2725 0.1894 0.1445 0.059 Uiso 1 1 calc R . . C14 C 0.7939(3) 0.4478(3) 0.1292(2) 0.0315(8) Uani 1 1 d . . . C15 C 0.9258(3) 0.5370(3) 0.1242(2) 0.0314(8) Uani 1 1 d . . . C16 C 0.9081(3) 0.6075(3) 0.0498(2) 0.0328(8) Uani 1 1 d . . . C17 C 1.0096(4) 0.7129(3) 0.0063(3) 0.0424(9) Uani 1 1 d . . . H17A H 0.9822 0.7161 -0.0623 0.064 Uiso 1 1 calc R . . H17B H 1.1016 0.7026 0.0106 0.064 Uiso 1 1 calc R . . H17C H 1.0118 0.7894 0.0420 0.064 Uiso 1 1 calc R . . C18 C 1.0548(3) 0.5484(3) 0.1832(3) 0.0365(8) Uani 1 1 d . . . H18A H 1.1350 0.5830 0.1427 0.044 Uiso 1 1 calc R . . H18B H 1.0550 0.4653 0.1998 0.044 Uiso 1 1 calc R . . C19 C 1.0734(3) 0.6293(3) 0.2781(3) 0.0389(9) Uani 1 1 d . . . H19A H 1.1620 0.6325 0.3116 0.047 Uiso 1 1 calc R . . H19B H 1.0799 0.7138 0.2612 0.047 Uiso 1 1 calc R . . C20 C 0.9583(4) 0.5861(3) 0.3489(3) 0.0418(9) Uani 1 1 d . . . H20A H 0.9829 0.6390 0.4098 0.050 Uiso 1 1 calc R . . H20B H 0.8722 0.5956 0.3199 0.050 Uiso 1 1 calc R . . C21 C 0.6580(3) 0.2440(3) 0.1875(3) 0.0387(9) Uani 1 1 d . . . C22 C 0.5741(4) 0.1999(3) 0.1039(3) 0.0437(9) Uani 1 1 d . . . H22 H 0.5828 0.2487 0.0489 0.052 Uiso 1 1 calc R . . C23 C 0.4764(4) 0.0827(3) 0.1013(3) 0.0507(10) Uani 1 1 d . . . H23 H 0.4191 0.0522 0.0441 0.061 Uiso 1 1 calc R . . C24 C 0.4629(4) 0.0118(4) 0.1804(4) 0.0529(11) Uani 1 1 d . . . C25 C 0.5451(5) 0.0553(4) 0.2642(4) 0.0598(12) Uani 1 1 d . . . H25 H 0.5353 0.0062 0.3191 0.072 Uiso 1 1 calc R . . C26 C 0.6421(4) 0.1711(4) 0.2676(3) 0.0512(10) Uani 1 1 d . . . H26 H 0.6984 0.2012 0.3253 0.061 Uiso 1 1 calc R . . Cl1 Cl -0.17283(15) -0.10161(13) 0.14429(16) 0.1223(8) Uani 1 1 d . . . Cl2 Cl 0.34190(13) -0.13432(10) 0.17514(12) 0.0855(5) Uani 1 1 d . . . N1 N 0.2562(3) 0.5423(3) 0.4741(2) 0.0434(8) Uani 1 1 d . . . H1A H 0.2135 0.5698 0.5203 0.052 Uiso 1 1 calc R . . N2 N 0.1948(3) 0.4386(3) 0.4150(2) 0.0413(8) Uani 1 1 d . . . N3 N 0.2808(3) 0.3418(3) 0.2828(2) 0.0440(8) Uani 1 1 d . . . N4 N 0.7749(3) 0.5621(3) 0.0159(2) 0.0364(7) Uani 1 1 d . . . H4 H 0.7392 0.5931 -0.0319 0.044 Uiso 1 1 calc R . . N5 N 0.7023(3) 0.4626(2) 0.0645(2) 0.0340(7) Uani 1 1 d . . . N6 N 0.7626(3) 0.3572(3) 0.1972(2) 0.0421(8) Uani 1 1 d . . . O1 O 0.4456(2) 0.4582(2) 0.12759(17) 0.0388(6) Uani 1 1 d . . . H1 H 0.5188 0.4526 0.1041 0.058 Uiso 1 1 calc R . . O2 O 0.9329(2) 0.4594(2) 0.37263(18) 0.0399(6) Uani 1 1 d . . . H2 H 1.0075 0.4490 0.3916 0.060 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 C1 0.0264(18) 0.053(2) 0.035(2) 0.0078(16) -0.0023(15) 0.0130(16) C2 0.0277(18) 0.051(2) 0.042(2) 0.0085(17) 0.0002(16) 0.0149(16) C3 0.035(2) 0.056(2) 0.037(2) 0.0031(17) -0.0043(17) 0.0158(17) C4 0.049(2) 0.064(3) 0.057(3) -0.004(2) -0.001(2) 0.018(2) C5 0.0258(18) 0.056(2) 0.041(2) 0.0020(17) -0.0037(16) 0.0140(16) C6 0.0284(18) 0.043(2) 0.049(2) 0.0017(16) 0.0027(17) 0.0071(15) C7 0.0335(19) 0.046(2) 0.048(2) 0.0062(17) -0.0013(17) 0.0170(16) C8 0.0324(19) 0.0370(19) 0.054(2) 0.0149(17) 0.0083(17) 0.0137(15) C9 0.042(2) 0.045(2) 0.078(3) 0.002(2) 0.026(2) 0.0103(18) C10 0.046(2) 0.046(2) 0.120(4) -0.002(3) 0.040(3) 0.005(2) C11 0.046(2) 0.038(2) 0.114(4) -0.006(2) 0.025(3) 0.0010(19) C12 0.056(3) 0.037(2) 0.087(3) 0.000(2) 0.023(2) 0.0097(19) C13 0.041(2) 0.043(2) 0.062(3) 0.0029(18) 0.014(2) 0.0111(17) C14 0.0221(16) 0.0371(18) 0.0337(19) -0.0023(14) -0.0011(15) 0.0077(14) C15 0.0227(16) 0.0349(18) 0.0358(19) -0.0037(15) 0.0002(15) 0.0087(13) C16 0.0262(17) 0.0337(17) 0.038(2) -0.0060(14) 0.0021(15) 0.0093(14) C17 0.041(2) 0.037(2) 0.047(2) 0.0008(16) -0.0014(18) 0.0089(16) C18 0.0203(16) 0.044(2) 0.042(2) 0.0037(16) 0.0002(15) 0.0064(14) C19 0.0270(18) 0.0402(19) 0.044(2) -0.0005(16) -0.0069(16) 0.0037(15) C20 0.035(2) 0.049(2) 0.040(2) -0.0059(16) -0.0031(17) 0.0124(16) C21 0.0249(17) 0.040(2) 0.047(2) -0.0015(16) 0.0028(17) 0.0050(15) C22 0.033(2) 0.045(2) 0.052(2) 0.0010(18) -0.0009(18) 0.0113(16) C23 0.034(2) 0.042(2) 0.072(3) -0.010(2) -0.004(2) 0.0075(17) C24 0.034(2) 0.037(2) 0.081(3) 0.000(2) 0.002(2) 0.0027(17) C25 0.058(3) 0.045(2) 0.070(3) 0.014(2) 0.008(2) 0.005(2) C26 0.045(2) 0.049(2) 0.051(2) 0.0029(19) 0.000(2) 0.0020(18) Cl1 0.0726(9) 0.0596(8) 0.2056(19) -0.0464(10) 0.0527(11) -0.0192(7) Cl2 0.0627(8) 0.0413(6) 0.1345(13) 0.0062(7) -0.0029(8) -0.0097(5) N1 0.0377(17) 0.058(2) 0.0379(18) 0.0015(15) 0.0034(15) 0.0199(15) N2 0.0323(16) 0.0552(19) 0.0374(17) 0.0021(14) 0.0029(14) 0.0153(14) N3 0.0280(16) 0.0508(19) 0.0497(19) -0.0030(15) 0.0066(14) 0.0073(14) N4 0.0271(15) 0.0400(16) 0.0434(17) 0.0037(13) -0.0015(13) 0.0123(12) N5 0.0234(14) 0.0376(16) 0.0387(17) 0.0026(12) -0.0021(13) 0.0062(12) N6 0.0296(16) 0.0396(17) 0.0498(19) 0.0026(14) -0.0004(14) 0.0002(13) O1 0.0231(12) 0.0456(14) 0.0467(15) 0.0025(11) 0.0025(11) 0.0091(10) O2 0.0265(12) 0.0471(15) 0.0422(15) 0.0027(11) -0.0011(12) 0.0057(11) _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 C1 N2 1.331(4) . ? C1 N3 1.394(5) . ? C1 C2 1.408(5) . ? C2 C3 1.375(5) . ? C2 C5 1.509(4) . ? C3 N1 1.357(4) . ? C3 C4 1.488(5) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.530(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.506(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O1 1.434(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N3 1.381(4) . ? C8 C13 1.390(5) . ? C8 C9 1.388(5) . ? C9 C10 1.364(6) . ? C9 H9 0.9500 . ? C10 C11 1.390(6) . ? C10 H10 0.9500 . ? C11 C12 1.369(5) . ? C11 Cl1 1.742(4) . ? C12 C13 1.376(5) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 N5 1.323(4) . ? C14 N6 1.397(4) . ? C14 C15 1.422(4) . ? C15 C16 1.371(5) . ? C15 C18 1.489(5) . ? C16 N4 1.354(4) . ? C16 C17 1.489(4) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.539(5) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.522(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O2 1.449(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.387(5) . ? C21 C26 1.393(5) . ? C21 N6 1.400(4) . ? C22 C23 1.402(5) . ? C22 H22 0.9500 . ? C23 C24 1.370(6) . ? C23 H23 0.9500 . ? C24 C25 1.381(6) . ? C24 Cl2 1.745(4) . ? C25 C26 1.388(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? N1 N2 1.375(4) . ? N1 H1A 0.8800 . ? N4 N5 1.367(4) . ? N4 H4 0.8800 . ? O1 H1 0.8400 . ? O2 H2 0.8400 . ? 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 N2 C1 N3 124.5(3) . . ? N2 C1 C2 112.7(3) . . ? N3 C1 C2 122.8(3) . . ? C3 C2 C1 104.7(3) . . ? C3 C2 C5 127.1(3) . . ? C1 C2 C5 128.1(3) . . ? N1 C3 C2 106.6(3) . . ? N1 C3 C4 122.7(3) . . ? C2 C3 C4 130.7(3) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 C6 114.9(3) . . ? C2 C5 H5A 108.5 . . ? C6 C5 H5A 108.5 . . ? C2 C5 H5B 108.5 . . ? C6 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? C7 C6 C5 114.6(3) . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6B 108.6 . . ? C5 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? O1 C7 C6 113.9(3) . . ? O1 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? O1 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? N3 C8 C13 116.8(3) . . ? N3 C8 C9 125.8(3) . . ? C13 C8 C9 117.4(4) . . ? C10 C9 C8 120.6(4) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 121.4(4) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C12 C11 C10 118.7(4) . . ? C12 C11 Cl1 121.1(4) . . ? C10 C11 Cl1 120.2(3) . . ? C11 C12 C13 119.8(4) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C8 122.1(3) . . ? C12 C13 H13 119.0 . . ? C8 C13 H13 119.0 . . ? N5 C14 N6 123.6(3) . . ? N5 C14 C15 112.5(3) . . ? N6 C14 C15 123.9(3) . . ? C16 C15 C14 103.8(3) . . ? C16 C15 C18 128.0(3) . . ? C14 C15 C18 128.2(3) . . ? N4 C16 C15 107.5(3) . . ? N4 C16 C17 122.4(3) . . ? C15 C16 C17 130.1(3) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 C19 114.4(3) . . ? C15 C18 H18A 108.7 . . ? C19 C18 H18A 108.7 . . ? C15 C18 H18B 108.7 . . ? C19 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C20 C19 C18 114.7(3) . . ? C20 C19 H19A 108.6 . . ? C18 C19 H19A 108.6 . . ? C20 C19 H19B 108.6 . . ? C18 C19 H19B 108.6 . . ? H19A C19 H19B 107.6 . . ? O2 C20 C19 113.0(3) . . ? O2 C20 H20A 109.0 . . ? C19 C20 H20A 109.0 . . ? O2 C20 H20B 109.0 . . ? C19 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? C22 C21 C26 119.1(3) . . ? C22 C21 N6 124.6(3) . . ? C26 C21 N6 116.3(3) . . ? C21 C22 C23 119.6(4) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C24 C23 C22 120.6(4) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C25 120.3(4) . . ? C23 C24 Cl2 119.9(3) . . ? C25 C24 Cl2 119.8(3) . . ? C24 C25 C26 119.5(4) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C25 C26 C21 120.9(4) . . ? C25 C26 H26 119.5 . . ? C21 C26 H26 119.5 . . ? C3 N1 N2 112.7(3) . . ? C3 N1 H1A 123.6 . . ? N2 N1 H1A 123.6 . . ? C1 N2 N1 103.3(3) . . ? C8 N3 C1 130.5(3) . . ? C16 N4 N5 112.2(3) . . ? C16 N4 H4 123.9 . . ? N5 N4 H4 123.9 . . ? C14 N5 N4 104.0(3) . . ? C14 N6 C21 126.8(3) . . ? C7 O1 H1 109.5 . . ? C20 O2 H2 109.5 . . ? 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 H1 N5 0.84 1.93 2.764(3) 170.6 . O2 H2 N2 0.84 1.96 2.796(4) 169.9 1_655 N1 H1A O2 0.88 2.09 2.891(4) 151.3 2_666 N4 H4 O1 0.88 2.17 2.889(4) 138.4 2_665 _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.637 _refine_diff_density_min -0.554 _refine_diff_density_rms 0.076 data_3 _database_code_depnum_ccdc_archive 'CCDC 830538' #TrackingRef '2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'C14 H17 Cl0 N3 O' _chemical_melting_point ? _chemical_formula_moiety 'C14 H17 Cl0 N3 O' _chemical_formula_sum 'C14 H17 Cl0 N3 O' _chemical_formula_weight 243.31 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 orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.012(3) _cell_length_b 9.445(2) _cell_length_c 15.967(4) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 1359.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.52 _cell_measurement_theta_max 30.82 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.92 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Bruker APEX CCD area-detector' _diffrn_measurement_method 'w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% NO _diffrn_reflns_number 8510 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 26.05 _reflns_number_total 2677 _reflns_number_gt 2206 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0818P)^2^+0.2553P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(3) _refine_ls_number_reflns 2677 _refine_ls_number_parameters 171 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1480 _refine_ls_wR_factor_gt 0.1391 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 C1 C 0.3075(3) -0.2804(3) 0.20358(16) 0.0370(7) Uani 1 1 d . . . C2 C 0.4544(3) -0.2622(3) 0.18471(16) 0.0343(6) Uani 1 1 d . . . C3 C 0.4534(3) -0.1649(3) 0.11745(15) 0.0303(6) Uani 1 1 d . . . C4 C 0.0681(4) -0.1830(4) 0.1454(2) 0.0562(9) Uani 1 1 d . . . H4A H 0.0446 -0.1175 0.1014 0.084 Uiso 1 1 calc R . . H4B H 0.0305 -0.1476 0.1976 0.084 Uiso 1 1 calc R . . H4C H 0.0235 -0.2731 0.1334 0.084 Uiso 1 1 calc R . . C5 C 0.2364(4) -0.3682(4) 0.27064(19) 0.0545(9) Uani 1 1 d . . . H5A H 0.1306 -0.3585 0.2674 0.082 Uiso 1 1 calc R . . H5B H 0.2702 -0.3366 0.3245 0.082 Uiso 1 1 calc R . . H5C H 0.2631 -0.4657 0.2630 0.082 Uiso 1 1 calc R . . C6 C 0.5901(3) -0.3221(3) 0.22677(17) 0.0407(7) Uani 1 1 d . . . C7 C 0.6402(4) -0.4662(3) 0.19315(19) 0.0450(8) Uani 1 1 d . . . H7A H 0.7316 -0.4930 0.2210 0.054 Uiso 1 1 calc R . . H7B H 0.5657 -0.5363 0.2073 0.054 Uiso 1 1 calc R . . C8 C 0.6652(3) -0.4691(3) 0.09960(18) 0.0404(7) Uani 1 1 d . . . H8A H 0.7021 -0.5614 0.0830 0.048 Uiso 1 1 calc R . . H8B H 0.5721 -0.4525 0.0708 0.048 Uiso 1 1 calc R . . C9 C 0.5921(3) -0.0044(3) 0.02027(16) 0.0308(6) Uani 1 1 d . . . C10 C 0.4913(3) 0.1076(3) 0.01601(18) 0.0336(6) Uani 1 1 d . . . H10 H 0.4088 0.1085 0.0509 0.040 Uiso 1 1 calc R . . C11 C 0.5138(3) 0.2172(3) -0.04001(17) 0.0380(7) Uani 1 1 d . . . H11 H 0.4452 0.2907 -0.0428 0.046 Uiso 1 1 calc R . . C12 C 0.6364(3) 0.2195(3) -0.09187(18) 0.0427(7) Uani 1 1 d . . . H12 H 0.6509 0.2940 -0.1291 0.051 Uiso 1 1 calc R . . C13 C 0.7375(3) 0.1089(3) -0.08766(19) 0.0419(7) Uani 1 1 d . . . H13 H 0.8204 0.1092 -0.1223 0.050 Uiso 1 1 calc R . . C14 C 0.7159(3) -0.0015(3) -0.03236(16) 0.0350(6) Uani 1 1 d . . . H14 H 0.7847 -0.0749 -0.0301 0.042 Uiso 1 1 calc R . . N1 N 0.2266(3) -0.1993(2) 0.15098(14) 0.0382(6) Uani 1 1 d . . . N2 N 0.3162(2) -0.1255(2) 0.09654(14) 0.0370(6) Uani 1 1 d . . . N3 N 0.5800(3) -0.1169(3) 0.07634(16) 0.0375(6) Uani 1 1 d . . . O1 O 0.7692(2) -0.3632(2) 0.07697(14) 0.0388(5) Uani 1 1 d . . . H1N H 0.643(3) -0.187(4) 0.0698(19) 0.042(8) Uiso 1 1 d . . . H1O H 0.778(4) -0.381(5) 0.026(3) 0.080(14) 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 C1 0.0524(18) 0.0298(14) 0.0289(13) -0.0030(11) 0.0058(12) -0.0035(13) C2 0.0473(17) 0.0296(14) 0.0261(13) -0.0047(11) 0.0020(11) -0.0009(12) C3 0.0336(14) 0.0311(14) 0.0261(13) -0.0004(11) 0.0013(10) 0.0008(11) C4 0.0409(17) 0.059(2) 0.069(2) 0.0059(19) 0.0079(16) -0.0014(16) C5 0.067(2) 0.0507(19) 0.0461(18) 0.0044(15) 0.0186(16) -0.0082(17) C6 0.0511(18) 0.0426(16) 0.0283(14) 0.0017(13) -0.0056(12) 0.0064(14) C7 0.0476(18) 0.0400(17) 0.0473(17) 0.0141(14) 0.0025(14) 0.0047(14) C8 0.0397(15) 0.0302(14) 0.0513(17) -0.0048(13) 0.0022(13) 0.0018(12) C9 0.0363(14) 0.0285(14) 0.0277(13) -0.0035(11) -0.0041(10) -0.0054(11) C10 0.0369(15) 0.0309(14) 0.0331(13) -0.0004(11) 0.0025(11) -0.0018(12) C11 0.0434(17) 0.0291(14) 0.0416(16) 0.0002(12) -0.0032(12) 0.0037(12) C12 0.0521(18) 0.0353(15) 0.0406(16) 0.0080(13) 0.0012(14) -0.0078(13) C13 0.0420(15) 0.0440(16) 0.0396(15) 0.0030(13) 0.0104(13) -0.0037(13) C14 0.0322(14) 0.0298(14) 0.0430(16) -0.0022(12) 0.0006(11) -0.0019(12) N1 0.0367(13) 0.0369(12) 0.0410(13) -0.0034(11) 0.0065(10) -0.0039(10) N2 0.0400(13) 0.0352(12) 0.0357(12) 0.0004(10) 0.0021(10) -0.0035(11) N3 0.0355(12) 0.0344(13) 0.0425(13) 0.0047(11) 0.0042(11) 0.0067(11) O1 0.0401(11) 0.0358(11) 0.0405(12) -0.0002(9) 0.0038(9) 0.0012(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 C1 N1 1.350(4) . ? C1 C2 1.369(4) . ? C1 C5 1.498(4) . ? C2 C3 1.413(4) . ? C2 C6 1.506(4) . ? C3 N2 1.333(3) . ? C3 N3 1.392(3) . ? C4 N1 1.439(4) . ? C6 C7 1.531(4) . ? C7 C8 1.511(4) . ? C8 O1 1.418(3) . ? C9 N3 1.394(4) . ? C9 C10 1.395(4) . ? C9 C14 1.398(4) . ? C10 C11 1.383(4) . ? C11 C12 1.380(4) . ? C12 C13 1.388(4) . ? C13 C14 1.380(4) . ? N1 N2 1.376(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 N1 C1 C2 108.3(2) . . ? N1 C1 C5 121.9(3) . . ? C2 C1 C5 129.8(3) . . ? C1 C2 C3 104.0(2) . . ? C1 C2 C6 129.8(3) . . ? C3 C2 C6 126.1(3) . . ? N2 C3 N3 123.4(2) . . ? N2 C3 C2 112.2(2) . . ? N3 C3 C2 124.4(2) . . ? C2 C6 C7 114.6(2) . . ? C8 C7 C6 114.0(2) . . ? O1 C8 C7 109.7(2) . . ? N3 C9 C10 123.9(2) . . ? N3 C9 C14 117.6(2) . . ? C10 C9 C14 118.4(2) . . ? C11 C10 C9 120.2(3) . . ? C12 C11 C10 121.1(3) . . ? C11 C12 C13 119.0(3) . . ? C14 C13 C12 120.5(3) . . ? C13 C14 C9 120.8(3) . . ? C1 N1 N2 111.3(2) . . ? C1 N1 C4 129.4(3) . . ? N2 N1 C4 119.3(3) . . ? C3 N2 N1 104.2(2) . . ? C3 N3 C9 128.0(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.445 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.046