#Supplementary Material (ESI) for Chemical Communications #This journal is (c) 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_address ;Department of Inorganic and Physical Chemistry Indian Institute of Science Bangalore 560 012. INDIA ; _publ_contact_author_email arc@ipc.iisc.ernet.in _publ_contact_author_fax 91-080-23600683 _publ_contact_author_phone 91-080-22932533 _publ_contact_author_name 'Prof. A. R. Chakravarty' _publ_author_name 'A. R. Chakravarty' data_arc1 _database_code_depnum_ccdc_archive 'CCDC 803983' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H8 Cl N3 O4 S' _chemical_formula_sum 'C13 H8 Cl N3 O4 S' _chemical_formula_weight 337.73 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' S S 0.1246 0.1234 '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 P21/n 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 7.9977(3) _cell_length_b 17.1647(6) _cell_length_c 9.7786(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.152(2) _cell_angle_gamma 90.00 _cell_volume 1338.86(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 30.53 _exptl_crystal_description plate _exptl_crystal_colour greenish-yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.464 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.878 _exptl_absorpt_correction_T_max 0.920 _exptl_absorpt_process_details SADABS(Sheldrick,1997) _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Smart CCD Area Detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15171 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 30.53 _reflns_number_total 4081 _reflns_number_gt 2457 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.1139P)^2^+0.4783P] 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 SHELXL _refine_ls_extinction_coef 0.033(3) _refine_ls_number_reflns 4081 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0909 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1688 _refine_ls_wR_factor_gt 0.1308 _refine_ls_goodness_of_fit_ref 0.822 _refine_ls_restrained_S_all 0.822 _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 0.32548(8) 0.13715(4) -0.01280(6) 0.04140(18) Uani 1 1 d . . . S1 S -0.10257(9) 0.24744(4) 0.14926(7) 0.0461(2) Uani 1 1 d . . . O1 O 0.4552(3) 0.12379(15) -0.1018(3) 0.0713(7) Uani 1 1 d . . . O2 O 0.2701(3) 0.06455(13) 0.0396(3) 0.0693(7) Uani 1 1 d . . . O3 O 0.1868(3) 0.17424(13) -0.0889(3) 0.0687(6) Uani 1 1 d . . . O4 O 0.3858(3) 0.18636(14) 0.0972(2) 0.0765(7) Uani 1 1 d . . . N1 N 0.1842(3) 0.14223(12) 0.4294(2) 0.0385(5) Uani 1 1 d . . . N2 N 0.1132(3) 0.19866(12) 0.3563(2) 0.0434(5) Uani 1 1 d . . . N3 N -0.0288(2) 0.10587(11) 0.20675(19) 0.0323(4) Uani 1 1 d . . . C1 C 0.2873(3) -0.13203(15) 0.5177(3) 0.0440(6) Uani 1 1 d . . . H1 H 0.2716 -0.1838 0.4919 0.053 Uiso 1 1 calc R . . C2 C 0.3859(3) -0.11421(18) 0.6337(3) 0.0496(7) Uani 1 1 d . . . H2 H 0.4382 -0.1540 0.6853 0.059 Uiso 1 1 calc R . . C3 C 0.4089(3) -0.03691(17) 0.6754(3) 0.0448(6) Uani 1 1 d . . . H3 H 0.4751 -0.0257 0.7550 0.054 Uiso 1 1 calc R . . C4 C 0.3342(3) 0.02275(16) 0.5995(2) 0.0392(5) Uani 1 1 d . . . H4 H 0.3499 0.0741 0.6282 0.047 Uiso 1 1 calc R . . C5 C 0.2338(3) 0.00631(13) 0.4782(2) 0.0323(5) Uani 1 1 d . . . C6 C 0.2091(3) -0.07218(14) 0.4370(2) 0.0356(5) Uani 1 1 d . . . C7 C 0.1041(3) -0.08969(15) 0.3172(3) 0.0411(6) Uani 1 1 d . . . H7 H 0.0894 -0.1415 0.2912 0.049 Uiso 1 1 calc R . . C8 C 0.0244(3) -0.03311(14) 0.2392(2) 0.0382(5) Uani 1 1 d . . . H8 H -0.0449 -0.0459 0.1620 0.046 Uiso 1 1 calc R . . C9 C 0.0495(3) 0.04524(13) 0.2785(2) 0.0314(5) Uani 1 1 d . . . C10 C 0.1537(3) 0.06665(13) 0.3936(2) 0.0313(5) Uani 1 1 d . . . C11 C 0.0063(3) 0.18023(14) 0.2484(2) 0.0377(5) Uani 1 1 d . . . C12 C -0.1936(3) 0.17449(16) 0.0520(3) 0.0431(6) Uani 1 1 d . . . H12 H -0.2700 0.1834 -0.0227 0.052 Uiso 1 1 calc R . . C13 C -0.1446(3) 0.10274(16) 0.0935(2) 0.0392(5) Uani 1 1 d . . . H13 H -0.1832 0.0568 0.0518 0.047 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 0.0442(3) 0.0362(3) 0.0427(3) -0.0016(2) -0.0043(2) -0.0048(2) S1 0.0520(4) 0.0357(3) 0.0490(4) 0.0038(3) -0.0075(3) 0.0070(3) O1 0.0604(13) 0.0789(17) 0.0771(16) -0.0133(13) 0.0215(12) -0.0112(12) O2 0.0792(16) 0.0516(13) 0.0776(16) 0.0194(12) 0.0088(13) -0.0122(11) O3 0.0646(13) 0.0512(13) 0.0853(16) 0.0039(12) -0.0282(12) 0.0026(11) O4 0.1004(18) 0.0640(15) 0.0602(14) -0.0243(12) -0.0279(12) 0.0044(13) N1 0.0409(11) 0.0328(10) 0.0405(11) -0.0043(8) -0.0065(8) 0.0025(8) N2 0.0510(12) 0.0295(10) 0.0478(12) -0.0034(9) -0.0091(10) -0.0004(9) N3 0.0325(9) 0.0321(10) 0.0320(9) -0.0015(8) -0.0007(7) -0.0003(8) C1 0.0482(14) 0.0345(13) 0.0499(15) 0.0069(11) 0.0081(11) 0.0060(11) C2 0.0438(14) 0.0517(16) 0.0538(16) 0.0206(13) 0.0073(12) 0.0111(12) C3 0.0383(12) 0.0540(16) 0.0415(14) 0.0078(12) -0.0012(10) 0.0018(11) C4 0.0373(12) 0.0421(13) 0.0380(13) 0.0027(10) -0.0002(10) -0.0010(10) C5 0.0300(10) 0.0330(11) 0.0339(11) 0.0013(9) 0.0025(8) 0.0005(9) C6 0.0376(12) 0.0323(12) 0.0374(12) 0.0028(9) 0.0069(9) 0.0037(9) C7 0.0493(14) 0.0312(12) 0.0427(13) -0.0040(10) 0.0026(11) -0.0011(10) C8 0.0428(12) 0.0355(12) 0.0356(12) -0.0071(10) -0.0015(10) -0.0038(10) C9 0.0327(10) 0.0290(11) 0.0322(11) -0.0003(9) 0.0007(8) -0.0008(9) C10 0.0319(10) 0.0310(11) 0.0308(11) -0.0017(9) 0.0018(8) -0.0001(9) C11 0.0390(12) 0.0328(12) 0.0405(13) -0.0016(10) -0.0030(10) 0.0030(10) C12 0.0421(13) 0.0503(15) 0.0359(13) 0.0034(11) -0.0038(10) 0.0029(11) C13 0.0383(12) 0.0431(14) 0.0352(12) -0.0010(10) -0.0049(10) -0.0007(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.420(2) . ? Cl1 O4 1.424(2) . ? Cl1 O2 1.430(2) . ? Cl1 O3 1.439(2) . ? S1 C12 1.704(3) . ? S1 C11 1.705(2) . ? N1 N2 1.309(3) . ? N1 C10 1.361(3) . ? N2 C11 1.347(3) . ? N3 C11 1.363(3) . ? N3 C9 1.380(3) . ? N3 C13 1.392(3) . ? C1 C2 1.368(4) . ? C1 C6 1.414(3) . ? C1 H1 0.9300 . ? C2 C3 1.396(4) . ? C2 H2 0.9300 . ? C3 C4 1.375(3) . ? C3 H3 0.9300 . ? C4 C5 1.412(3) . ? C4 H4 0.9300 . ? C5 C6 1.416(3) . ? C5 C10 1.446(3) . ? C6 C7 1.423(3) . ? C7 C8 1.364(3) . ? C7 H7 0.9300 . ? C8 C9 1.409(3) . ? C8 H8 0.9300 . ? C9 C10 1.401(3) . ? C12 C13 1.346(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? 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 O1 Cl1 O4 109.65(16) . . ? O1 Cl1 O2 109.76(15) . . ? O4 Cl1 O2 110.03(15) . . ? O1 Cl1 O3 108.93(16) . . ? O4 Cl1 O3 109.55(14) . . ? O2 Cl1 O3 108.89(14) . . ? C12 S1 C11 90.01(12) . . ? N2 N1 C10 120.1(2) . . ? N1 N2 C11 118.7(2) . . ? C11 N3 C9 118.59(19) . . ? C11 N3 C13 112.6(2) . . ? C9 N3 C13 128.8(2) . . ? C2 C1 C6 120.4(3) . . ? C2 C1 H1 119.8 . . ? C6 C1 H1 119.8 . . ? C1 C2 C3 120.7(2) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 120.5(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.2(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 119.2(2) . . ? C4 C5 C10 122.6(2) . . ? C6 C5 C10 118.2(2) . . ? C1 C6 C5 119.0(2) . . ? C1 C6 C7 121.1(2) . . ? C5 C6 C7 119.8(2) . . ? C8 C7 C6 122.3(2) . . ? C8 C7 H7 118.9 . . ? C6 C7 H7 118.9 . . ? C7 C8 C9 118.4(2) . . ? C7 C8 H8 120.8 . . ? C9 C8 H8 120.8 . . ? N3 C9 C10 115.62(19) . . ? N3 C9 C8 122.1(2) . . ? C10 C9 C8 122.3(2) . . ? N1 C10 C9 122.8(2) . . ? N1 C10 C5 118.16(19) . . ? C9 C10 C5 119.0(2) . . ? N2 C11 N3 124.0(2) . . ? N2 C11 S1 123.75(19) . . ? N3 C11 S1 112.22(17) . . ? C13 C12 S1 113.62(19) . . ? C13 C12 H12 123.2 . . ? S1 C12 H12 123.2 . . ? C12 C13 N3 111.5(2) . . ? C12 C13 H13 124.2 . . ? N3 C13 H13 124.2 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.327 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.058 # Attachment 'cif_Compound 2.cif' data_arc2 _database_code_depnum_ccdc_archive 'CCDC 803984' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H10 Cl N3 O4' _chemical_formula_sum 'C15 H10 Cl N3 O4' _chemical_formula_weight 331.71 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 6.449(13) _cell_length_b 8.009(16) _cell_length_c 14.00(3) _cell_angle_alpha 77.16(3) _cell_angle_beta 84.58(3) _cell_angle_gamma 86.44(3) _cell_volume 701(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.50 _cell_measurement_theta_max 25.00 _exptl_crystal_description plate _exptl_crystal_colour greenish-yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.298 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.928 _exptl_absorpt_correction_T_max 0.948 _exptl_absorpt_process_details SADABS(Sheldrick,1997) _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Smart CCD Area Detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6714 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2480 _reflns_number_gt 2159 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.2000P)^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 SHELXL _refine_ls_extinction_coef 0.033(3) _refine_ls_number_reflns 2480 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1047 _refine_ls_R_factor_gt 0.0976 _refine_ls_wR_factor_ref 0.3247 _refine_ls_wR_factor_gt 0.3088 _refine_ls_goodness_of_fit_ref 1.482 _refine_ls_restrained_S_all 1.482 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.004 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 0.57847(15) 0.82393(12) 0.84314(7) 0.0602(5) Uani 1 1 d . . . O1 O 0.7915(7) 0.8402(8) 0.8549(4) 0.132(2) Uani 1 1 d . . . O2 O 0.5605(7) 0.8228(6) 0.7435(3) 0.1045(13) Uani 1 1 d . . . O3 O 0.4568(10) 0.9602(7) 0.8655(4) 0.1340(19) Uani 1 1 d . . . O4 O 0.5125(7) 0.6661(6) 0.9064(4) 0.1130(14) Uani 1 1 d . . . N1 N 1.1890(6) 0.6995(6) 0.6378(4) 0.0832(13) Uani 1 1 d . . . N2 N 1.2020(6) 0.7908(6) 0.5422(4) 0.0843(13) Uani 1 1 d . . . N3 N 0.8708(6) 0.6957(5) 0.5105(3) 0.0654(10) Uani 1 1 d . . . C1 C 0.7822(9) 0.2930(7) 0.8851(4) 0.0789(14) Uani 1 1 d . . . H1 H 0.6606 0.2330 0.9031 0.095 Uiso 1 1 calc R . . C2 C 0.9358(10) 0.2743(8) 0.9493(4) 0.0911(18) Uani 1 1 d . . . H2 H 0.9203 0.2001 1.0107 0.109 Uiso 1 1 calc R . . C3 C 1.1163(9) 0.3691(9) 0.9207(4) 0.0919(18) Uani 1 1 d . . . H3 H 1.2208 0.3583 0.9634 0.110 Uiso 1 1 calc R . . C4 C 1.1379(7) 0.4755(8) 0.8316(4) 0.0774(14) Uani 1 1 d . . . H4 H 1.2569 0.5389 0.8140 0.093 Uiso 1 1 calc R . . C5 C 0.9884(5) 0.4927(5) 0.7659(3) 0.0469(9) Uani 1 1 d . . . C6 C 0.8111(7) 0.4025(6) 0.7931(3) 0.0611(11) Uani 1 1 d . . . C7 C 0.6565(6) 0.4131(5) 0.7296(3) 0.0520(9) Uani 1 1 d . . . H7 H 0.5361 0.3524 0.7505 0.062 Uiso 1 1 calc R . . C8 C 0.6780(5) 0.5060(5) 0.6421(3) 0.0459(9) Uani 1 1 d . . . H8 H 0.5733 0.5112 0.6000 0.055 Uiso 1 1 calc R . . C9 C 0.8531(6) 0.5973(5) 0.6101(3) 0.0516(10) Uani 1 1 d . . . C10 C 1.0136(6) 0.5986(5) 0.6711(3) 0.0556(10) Uani 1 1 d . . . C11 C 1.0469(6) 0.7903(5) 0.4779(3) 0.0595(11) Uani 1 1 d . . . C12 C 1.0669(8) 0.8865(6) 0.3783(4) 0.0722(13) Uani 1 1 d . . . H12 H 1.1853 0.9487 0.3550 0.087 Uiso 1 1 calc R . . C13 C 0.9136(9) 0.8875(6) 0.3175(4) 0.0755(14) Uani 1 1 d . . . H13 H 0.9277 0.9516 0.2533 0.091 Uiso 1 1 calc R . . C14 C 0.7348(8) 0.7932(6) 0.3505(3) 0.0713(13) Uani 1 1 d . . . H14 H 0.6315 0.7950 0.3081 0.086 Uiso 1 1 calc R . . C15 C 0.7115(6) 0.6974(5) 0.4458(3) 0.0578(10) Uani 1 1 d . . . H15 H 0.5930 0.6347 0.4677 0.069 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 0.0624(8) 0.0582(8) 0.0613(8) -0.0109(5) -0.0116(5) -0.0101(5) O1 0.085(3) 0.179(5) 0.118(3) 0.027(3) -0.040(2) -0.057(3) O2 0.111(3) 0.129(4) 0.083(3) -0.036(2) -0.009(2) -0.037(3) O3 0.174(5) 0.110(4) 0.122(4) -0.045(3) -0.014(3) 0.028(3) O4 0.104(3) 0.097(3) 0.122(3) 0.013(2) -0.006(2) -0.028(2) N1 0.058(2) 0.085(3) 0.114(3) -0.038(3) -0.012(2) 0.003(2) N2 0.058(2) 0.072(3) 0.121(4) -0.022(3) 0.002(2) 0.0004(19) N3 0.062(2) 0.060(2) 0.077(2) -0.0261(18) -0.0031(17) 0.0073(17) C1 0.086(3) 0.086(3) 0.067(3) -0.026(2) -0.004(2) 0.003(3) C2 0.108(5) 0.107(4) 0.057(3) -0.020(3) -0.015(3) 0.024(4) C3 0.074(3) 0.132(5) 0.076(3) -0.035(3) -0.031(3) 0.021(3) C4 0.056(3) 0.108(4) 0.077(3) -0.036(3) -0.016(2) 0.006(2) C5 0.0382(18) 0.057(2) 0.0524(19) -0.0272(16) -0.0092(14) 0.0099(15) C6 0.061(2) 0.065(3) 0.062(2) -0.026(2) -0.0078(18) 0.0103(19) C7 0.0417(18) 0.062(2) 0.056(2) -0.0213(18) -0.0024(15) -0.0085(16) C8 0.0384(17) 0.050(2) 0.053(2) -0.0180(16) -0.0092(14) -0.0034(14) C9 0.0447(19) 0.053(2) 0.062(2) -0.0254(17) -0.0064(16) 0.0104(15) C10 0.0386(18) 0.059(2) 0.078(3) -0.035(2) -0.0054(16) 0.0046(16) C11 0.048(2) 0.048(2) 0.085(3) -0.025(2) 0.0039(18) 0.0025(16) C12 0.076(3) 0.051(2) 0.085(3) -0.017(2) 0.021(2) 0.000(2) C13 0.090(4) 0.057(3) 0.076(3) -0.016(2) 0.007(3) 0.006(2) C14 0.090(3) 0.061(3) 0.065(3) -0.020(2) -0.009(2) 0.010(2) C15 0.056(2) 0.054(2) 0.067(2) -0.0195(18) -0.0070(17) 0.0020(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O3 1.380(5) . ? Cl1 O2 1.412(5) . ? Cl1 O1 1.416(5) . ? Cl1 O4 1.436(5) . ? N1 N2 1.372(7) . ? N1 C10 1.413(7) . ? N2 C11 1.408(7) . ? N3 C11 1.388(6) . ? N3 C15 1.429(6) . ? N3 C9 1.439(6) . ? C1 C2 1.379(8) . ? C1 C6 1.391(7) . ? C1 H1 0.9300 . ? C2 C3 1.406(9) . ? C2 H2 0.9300 . ? C3 C4 1.346(8) . ? C3 H3 0.9300 . ? C4 C5 1.374(6) . ? C4 H4 0.9300 . ? C5 C6 1.369(6) . ? C5 C10 1.408(6) . ? C6 C7 1.383(6) . ? C7 C8 1.284(5) . ? C7 H7 0.9300 . ? C8 C9 1.368(6) . ? C8 H8 0.9300 . ? C9 C10 1.405(6) . ? C11 C12 1.434(7) . ? C12 C13 1.363(8) . ? C12 H12 0.9300 . ? C13 C14 1.402(8) . ? C13 H13 0.9300 . ? C14 C15 1.383(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? 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 O3 Cl1 O2 108.0(3) . . ? O3 Cl1 O1 111.6(4) . . ? O2 Cl1 O1 107.9(3) . . ? O3 Cl1 O4 110.3(4) . . ? O2 Cl1 O4 111.1(3) . . ? O1 Cl1 O4 108.0(3) . . ? N2 N1 C10 117.7(4) . . ? N1 N2 C11 122.8(4) . . ? C11 N3 C15 120.2(4) . . ? C11 N3 C9 118.5(4) . . ? C15 N3 C9 121.3(4) . . ? C2 C1 C6 119.3(6) . . ? C2 C1 H1 120.4 . . ? C6 C1 H1 120.4 . . ? C1 C2 C3 119.1(6) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 120.0(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 121.6(5) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C6 C5 C4 118.9(4) . . ? C6 C5 C10 119.1(3) . . ? C4 C5 C10 122.0(4) . . ? C5 C6 C7 121.5(4) . . ? C5 C6 C1 121.0(4) . . ? C7 C6 C1 117.5(5) . . ? C8 C7 C6 120.5(4) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 120.8(4) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C8 C9 C10 122.3(4) . . ? C8 C9 N3 118.3(4) . . ? C10 C9 N3 119.5(4) . . ? C9 C10 C5 115.8(4) . . ? C9 C10 N1 121.3(5) . . ? C5 C10 N1 122.9(4) . . ? N3 C11 N2 120.1(5) . . ? N3 C11 C12 118.7(4) . . ? N2 C11 C12 121.1(4) . . ? C13 C12 C11 120.4(5) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 120.8(5) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C15 C14 C13 120.2(5) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 N3 119.5(4) . . ? C14 C15 H15 120.3 . . ? N3 C15 H15 120.3 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.731 _refine_diff_density_min -0.709 _refine_diff_density_rms 0.163